CA2456556A1 - Method for repairing fuel tanks - Google Patents
Method for repairing fuel tanks Download PDFInfo
- Publication number
- CA2456556A1 CA2456556A1 CA002456556A CA2456556A CA2456556A1 CA 2456556 A1 CA2456556 A1 CA 2456556A1 CA 002456556 A CA002456556 A CA 002456556A CA 2456556 A CA2456556 A CA 2456556A CA 2456556 A1 CA2456556 A1 CA 2456556A1
- Authority
- CA
- Canada
- Prior art keywords
- amine
- occurrence
- separately
- complex
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000002828 fuel tank Substances 0.000 title claims abstract description 40
- 239000000853 adhesive Substances 0.000 claims abstract description 54
- 230000001070 adhesive effect Effects 0.000 claims abstract description 54
- 238000003825 pressing Methods 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 150000001412 amines Chemical class 0.000 claims description 51
- -1 alkyl cycloalkyl borane Chemical compound 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 25
- 150000003141 primary amines Chemical class 0.000 claims description 23
- 150000002466 imines Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- 229910000085 borane Inorganic materials 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 150000001409 amidines Chemical class 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000446 fuel Substances 0.000 claims description 10
- 229920001903 high density polyethylene Polymers 0.000 claims description 10
- 239000004700 high-density polyethylene Substances 0.000 claims description 10
- 239000010410 layer Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000004888 barrier function Effects 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
- 230000009878 intermolecular interaction Effects 0.000 claims description 6
- 230000008863 intramolecular interaction Effects 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000002356 single layer Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004715 ethylene vinyl alcohol Substances 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 claims description 2
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 claims description 2
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 239000002650 laminated plastic Substances 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920006163 vinyl copolymer Polymers 0.000 claims description 2
- 239000002759 woven fabric Substances 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 21
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 18
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 229910000906 Bronze Inorganic materials 0.000 claims 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000010974 bronze Substances 0.000 claims 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000010935 stainless steel Substances 0.000 claims 1
- 229910001220 stainless steel Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 241000282337 Nasua nasua Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920000571 Nylon 11 Polymers 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 229920006226 ethylene-acrylic acid Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000003856 thermoforming Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000004046 wet winding Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- VWSLLSXLURJCDF-UHFFFAOYSA-N 2-methyl-4,5-dihydro-1h-imidazole Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- FRAKHUZTNLUGPB-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C2NCC1(C)CC(C)(C)C2 FRAKHUZTNLUGPB-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- CXOSLKWXWSIHIO-UHFFFAOYSA-N 3-imino-1-n,1-n,2-n,2-n-tetramethylcyclopropene-1,2-diamine Chemical compound CN(C)C1=C(N(C)C)C1=N CXOSLKWXWSIHIO-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- UTOXFQVLOTVLSD-UHFFFAOYSA-N 3-propoxypropan-1-amine Chemical compound CCCOCCCN UTOXFQVLOTVLSD-UHFFFAOYSA-N 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920000577 Nylon 6/66 Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000004957 Zytel Substances 0.000 description 1
- 229920006102 Zytel® Polymers 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- TZYHIGCKINZLPD-UHFFFAOYSA-N azepan-2-one;hexane-1,6-diamine;hexanedioic acid Chemical compound NCCCCCCN.O=C1CCCCCN1.OC(=O)CCCCC(O)=O TZYHIGCKINZLPD-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012792 core layer Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- UUZLJPRHSPEASP-UHFFFAOYSA-N cyclohexylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCCCC1 UUZLJPRHSPEASP-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IZOKYNNJMLYHSO-UHFFFAOYSA-N hexane-1,4,4-triamine Chemical compound CCC(N)(N)CCCN IZOKYNNJMLYHSO-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 229920004889 linear high-density polyethylene Polymers 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000007746 phosphate conversion coating Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C73/00—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D
- B29C73/04—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements
- B29C73/06—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements using plugs sealing in the hole
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D90/00—Component parts, details or accessories for large containers
- B65D90/02—Wall construction
- B65D90/06—Coverings, e.g. for insulating purposes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C73/00—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D
- B29C73/04—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements
- B29C73/10—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements using patches sealing on the surface of the article
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/12—Materials for stopping leaks, e.g. in radiators, in tanks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C73/00—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D
- B29C73/24—Apparatus or accessories not otherwise provided for
- B29C73/26—Apparatus or accessories not otherwise provided for for mechanical pretreatment
- B29C2073/264—Apparatus or accessories not otherwise provided for for mechanical pretreatment for cutting out or grooving the area to be repaired
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C73/00—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D
- B29C73/04—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements
- B29C73/10—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements using patches sealing on the surface of the article
- B29C73/105—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using preformed elements using patches sealing on the surface of the article provided with a centering element
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2031/00—Other particular articles
- B29L2031/712—Containers; Packaging elements or accessories, Packages
- B29L2031/7172—Fuel tanks, jerry cans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/16—Metal
- C09J2400/163—Metal in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/22—Presence of unspecified polymer
- C09J2400/226—Presence of unspecified polymer in the substrate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T29/00—Metal working
- Y10T29/49—Method of mechanical manufacture
- Y10T29/49718—Repairing
- Y10T29/49732—Repairing by attaching repair preform, e.g., remaking, restoring, or patching
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T29/00—Metal working
- Y10T29/49—Method of mechanical manufacture
- Y10T29/49718—Repairing
- Y10T29/49732—Repairing by attaching repair preform, e.g., remaking, restoring, or patching
- Y10T29/49734—Repairing by attaching repair preform, e.g., remaking, restoring, or patching and removing damaged material
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Cooling, Air Intake And Gas Exhaust, And Fuel Tank Arrangements In Propulsion Units (AREA)
- Rigid Containers With Two Or More Constituent Elements (AREA)
- Sealing Material Composition (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
A method for repairing fuel tanks having detected leaks comprises (1) fillin g the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks or (2) providing a fuel tank having a surface with detected leaks, providing a patch having a surface to be attached to the fuel tank surface having detected leaks, coati ng one or both surfaces with an adhesive, applying the patch over the detected leak(s) such that the adhesive is interposed between the patch surface and t he tank surface, pressing the patch against the tank and allowing the adhesive to cure to bond the two surfaces together.
Description
METHOD FOR REPAIRING FUEL TANKS
The present invention relates to fuel tanks and, more particularly, to methods for repairing fuel tanks.
Fuel tanks can be damaged during the production process or during use.
Presently, fuel tanks are repaired by welding, soldering, or gluing the local spot that appears to be leaking.
Because replacement fuel tanks are quite costly, it would be desirable to have a method for repairing fuel tanks which is less expensive than a replacement tank, and which is easily and speedily performed.
In a f rst aspect, the present invention is a method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, filling the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks.
In a second aspect, the present invention is a method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, providing a patch having a surface to be attached to the fuel tank surface, coating the tank surface and/or the patch surface with an adhesive, placing the patch over the detected leaks) such that the adhesive is interposed between the tank surface and the patch surface, pressing the patch against the tank and allowing the adhesive to cure to bond the two surfaces together.
Figs. 1 a, 1b and 1 c show patch or plug designs used for in-plant repairs.
Fig. 1 C shows a "donut" design of a "patch" or "plug" for redundant sealing mechanism.
Figs. 2a, 2b and 2c show patch or plug designs used for after-market and/or warranty repairs.
The fuel tank, patch and/or plug can be made of metal or a monolayer or multilayer plastic laminate.
The patch can be made also of woven or non-woven fabric or a composite material, such as a fiber composite.
Preferably, the fuel tank, patch and/or plug comprise a multilayer laminate structure having one or more layers of a low energy surface material and one or more layers of a polymer having fuel barrier property.
More preferably, the fuel tank, patch and/or plug comprise a three-layer laminate structure having two outer layers of a low energy surface material and a core layer of a polymer having fuel barrier property.
The multilayer or three-layer laminate structure can be prepared by known techniques, such as co-extrusion or slot casting, both of which are known in the art.
The patches can be prepared by cutting a piece of metal or a monolayer or multilayer laminate structure or fiber composite into the desired size and shape for the patch, or by using conventional thermoforming techniques. A typical thermoforming process comprises heating a thermoplastic sheet to its softening point and then shaping the sheet at a forming station utilizing various molds and/or vacuum or air pressure assists or plug assists.
The plugs can be made by known processes, such as those described in U.S.
Patent Nos. 4,058,234; 4,160,465; 4,058,234; and 4,160,465 Composites, such as fiber composites, are known in the art and are described, for example, in U.S. Patent 5,458,258. A fiber composite typically comprises reinforcing fibers or filaments embedded in a resin matrix. The resin can be applied on the filaments using either the prepreg method or the wet winding method. In the prepreg method, the filament is impregnated with a liquid resin and partially cured and then usually stored at low temperature to retard the curing process until required for winding. In the wet winding method, the filaments are impregnated with liquid resin just before winding on the mandrel.
The low energy surface materials which can be employed in the practice of the present invention include any material which meets original equipment manufacturers' (OEM) requirements, such as, for example, polyolefins, polytetrafluoroethylene (PTFE), polyethylene terephthalate (PET), acetal (polyoxymethylene) hornopolymers and copolymers, nylon, poly(butylene terephalate) (PBT), liquid crystal polymers, polyvinylidene fluoride (PVDF), polyvinylidene chloride (PVDC) and ethylene vinyl alcohol (EVOH).
The polyolefins which can be employed in the practice of the present invention for preparing the multilayer laminate structure include polypropylene, polyethylene, and copolymers and blends thereof, as well as ethylene-propylene-dime terpolymers.
The present invention relates to fuel tanks and, more particularly, to methods for repairing fuel tanks.
Fuel tanks can be damaged during the production process or during use.
Presently, fuel tanks are repaired by welding, soldering, or gluing the local spot that appears to be leaking.
Because replacement fuel tanks are quite costly, it would be desirable to have a method for repairing fuel tanks which is less expensive than a replacement tank, and which is easily and speedily performed.
In a f rst aspect, the present invention is a method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, filling the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks.
In a second aspect, the present invention is a method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, providing a patch having a surface to be attached to the fuel tank surface, coating the tank surface and/or the patch surface with an adhesive, placing the patch over the detected leaks) such that the adhesive is interposed between the tank surface and the patch surface, pressing the patch against the tank and allowing the adhesive to cure to bond the two surfaces together.
Figs. 1 a, 1b and 1 c show patch or plug designs used for in-plant repairs.
Fig. 1 C shows a "donut" design of a "patch" or "plug" for redundant sealing mechanism.
Figs. 2a, 2b and 2c show patch or plug designs used for after-market and/or warranty repairs.
The fuel tank, patch and/or plug can be made of metal or a monolayer or multilayer plastic laminate.
The patch can be made also of woven or non-woven fabric or a composite material, such as a fiber composite.
Preferably, the fuel tank, patch and/or plug comprise a multilayer laminate structure having one or more layers of a low energy surface material and one or more layers of a polymer having fuel barrier property.
More preferably, the fuel tank, patch and/or plug comprise a three-layer laminate structure having two outer layers of a low energy surface material and a core layer of a polymer having fuel barrier property.
The multilayer or three-layer laminate structure can be prepared by known techniques, such as co-extrusion or slot casting, both of which are known in the art.
The patches can be prepared by cutting a piece of metal or a monolayer or multilayer laminate structure or fiber composite into the desired size and shape for the patch, or by using conventional thermoforming techniques. A typical thermoforming process comprises heating a thermoplastic sheet to its softening point and then shaping the sheet at a forming station utilizing various molds and/or vacuum or air pressure assists or plug assists.
The plugs can be made by known processes, such as those described in U.S.
Patent Nos. 4,058,234; 4,160,465; 4,058,234; and 4,160,465 Composites, such as fiber composites, are known in the art and are described, for example, in U.S. Patent 5,458,258. A fiber composite typically comprises reinforcing fibers or filaments embedded in a resin matrix. The resin can be applied on the filaments using either the prepreg method or the wet winding method. In the prepreg method, the filament is impregnated with a liquid resin and partially cured and then usually stored at low temperature to retard the curing process until required for winding. In the wet winding method, the filaments are impregnated with liquid resin just before winding on the mandrel.
The low energy surface materials which can be employed in the practice of the present invention include any material which meets original equipment manufacturers' (OEM) requirements, such as, for example, polyolefins, polytetrafluoroethylene (PTFE), polyethylene terephthalate (PET), acetal (polyoxymethylene) hornopolymers and copolymers, nylon, poly(butylene terephalate) (PBT), liquid crystal polymers, polyvinylidene fluoride (PVDF), polyvinylidene chloride (PVDC) and ethylene vinyl alcohol (EVOH).
The polyolefins which can be employed in the practice of the present invention for preparing the multilayer laminate structure include polypropylene, polyethylene, and copolymers and blends thereof, as well as ethylene-propylene-dime terpolymers.
The preferred polyolefins are polypropylene, linear high density polyethylene (HDPE), heterogeneously-branched linear low density polyethylene (LLDPE) such as DOWLEXTM polyethylene resin (a trademark of The Dow Chemical Company), heterogeneously branched ultra low linear density polyethylene (ULDPE) such as ATTANETM ULDPE (a trademark of The Dow Chemical Company); homogeneously-branched, linear ethylene/a-olefin copolymers such as TAFMERTM (a trademark of Mitsui Petrochemicals Company Limited) and EXACTTM (a trademark of Exxon Chemical Company); homogeneously branched, substantially linear ethylene/cx-olefin polymers such as AFFINITYTM (a trademark of The Dow Chemical Company) and ENGAGES (a trademark DuPont Dow Elastomers L.L. C) of polyolefin elastomers, which can be prepared as disclosed in U.S. Patents 5,272,236 and 5,278,272; and high pressure, free radical polymerized ethylene polymers and copolymers such as low density polyethylene (LDPE), ethylene-acrylic acid (EAA) copolymers such as PRIMACORTM (trademark of The Dow Chemical Company), and ethylene-vinyl acetate (EVA) copolymers such as ESCORENETM
polymers (a trademark of Exxon Chemical Company), and ELVAXTM (a trademark of E.I.
du Pont de Nemours & Co.).
The more preferred polyolefms are the homogeneously-branched linear and substantially linear ethylene copolymers with a density (measured in accordance with ASTM D-792) of 0.85 to 0.99 g/cm3, a weight average molecular weight to number average molecular weight ratio (Mw/Mn) from 1.5 to 3.0, a measured melt index (measured in accordance with ASTM D-1238 (190/2.16)) of 0.01 to 100 g/10 min, and an I10/I2 of 6 to 20 (measured in accordance with ASTM D-1238 (190/10)). The most preferred polyolefln is a high density polyethylene. In general, high density polyethylene (HDPE) has a density of at least 0.94 grams per cubic centimeter (g/cc) (ASTM Test Method D-1505).
HDPE is commonly produced using techniques similar to the preparation of linear low density polyethylenes. Such techniques are described in U.S. Patents 2,825,721;
2,993,876;
polymers (a trademark of Exxon Chemical Company), and ELVAXTM (a trademark of E.I.
du Pont de Nemours & Co.).
The more preferred polyolefms are the homogeneously-branched linear and substantially linear ethylene copolymers with a density (measured in accordance with ASTM D-792) of 0.85 to 0.99 g/cm3, a weight average molecular weight to number average molecular weight ratio (Mw/Mn) from 1.5 to 3.0, a measured melt index (measured in accordance with ASTM D-1238 (190/2.16)) of 0.01 to 100 g/10 min, and an I10/I2 of 6 to 20 (measured in accordance with ASTM D-1238 (190/10)). The most preferred polyolefln is a high density polyethylene. In general, high density polyethylene (HDPE) has a density of at least 0.94 grams per cubic centimeter (g/cc) (ASTM Test Method D-1505).
HDPE is commonly produced using techniques similar to the preparation of linear low density polyethylenes. Such techniques are described in U.S. Patents 2,825,721;
2,993,876;
3,250,825 and 4,204,050. The preferred HDPE employed in the practice of the present invention has a density of from 0.94 to 0.99 g/cc and a melt index of from 0.01 to 35 grams per 10 minutes as determined by ASTM Test Method D-1238.
The polymers having fuel barrier property which can be employed in the practice of the present invention for preparing the plastic fuel tank and the patch or plug include polyamides, polyetrafluroethylene (PTFE), polyamides, fluoroelastomers, polyacetal homopolymers and copolymers, sulfonated and fluorinated HDPE, ethylene vinyl alcohol polymers and copolymers, hydroxy-fixnctionalized polyethers and polyesters, and branched polyesters.
Specific examples of polyamides include nylon 6, nylon 66, nylon 610, nylon 9, nylon 11, nylon 12, nylon 6/66, nylon 66/610, nylon 6/11, AMODELTM, (a trademark of BP Amoco) and ZYTEL HTNTM (a trademark of E.I. du Pont de Nemours &
Co.).
The tie layer, also commonly referred to as an adhesive layer, which can be employed in the practice of the present invention for adhering one layer to an adjacent layer of the multilayer structure is made of an adhesive material, such as a modified polyethylene elastomer. Preferably, the adhesive material is a malefic anhydride grafted polyethylene or polypropylene such as ADMERT"" (trademark of Mitsui Petrochemicals) adhesive resin or ethylene-vinyl acetate copolymer resins such as ELVAXTM (trademark of DuPont).
The adhesives which can be employed in the practice of the present invention for repairing fuel tanks include those adhesives which can support a load of 1334N.
Advantageously, the adhesive has a fuel vapor permeation rate of not more than 46 g-mm/m2/day and, more advantageously, not more than 12 g-mm/m2/day, as determined by ASTM E 96 - 94.
Preferably the adhesives are those which bond to low energy surface plastic materials, such as the adhesive commercially known as LEA and described in an advertisement in the SPE Plastics Engineering magazine, March 2001 page 22;
and adhesives comprising an amine/organoborane complex, such as those described in a series ofpatents issued to Skoultchi (IJS PatentNos. 5,106,928, 5,143,884, 5,286,821, 5,310,835 and 5,376,746). These patents disclose a two-part initiator system that is reportedly usefixl in acrylic adhesive compositions. The first part of the two-part system includes a stable organoborane/amine complex and the second part includes a destabilizer or activator such as an organic acid or an aldehyde. The organoborane compound of the complex has three ligands which can be selected from Cl_io alkyl groups or phenyl groups. Useful amines disclosed include octylamine, 1,6 diaminohexane, diethylamine, dibutylamine, diethylenetriamine, dipropylenediamine, 1,3 propylene diamine, and 1,2 propylene diamine.
Other preferred adhesives which can be employed in the practice of the present invention for repairing fizel tanks include those adhesives disclosed by Zharov et al.
The polymers having fuel barrier property which can be employed in the practice of the present invention for preparing the plastic fuel tank and the patch or plug include polyamides, polyetrafluroethylene (PTFE), polyamides, fluoroelastomers, polyacetal homopolymers and copolymers, sulfonated and fluorinated HDPE, ethylene vinyl alcohol polymers and copolymers, hydroxy-fixnctionalized polyethers and polyesters, and branched polyesters.
Specific examples of polyamides include nylon 6, nylon 66, nylon 610, nylon 9, nylon 11, nylon 12, nylon 6/66, nylon 66/610, nylon 6/11, AMODELTM, (a trademark of BP Amoco) and ZYTEL HTNTM (a trademark of E.I. du Pont de Nemours &
Co.).
The tie layer, also commonly referred to as an adhesive layer, which can be employed in the practice of the present invention for adhering one layer to an adjacent layer of the multilayer structure is made of an adhesive material, such as a modified polyethylene elastomer. Preferably, the adhesive material is a malefic anhydride grafted polyethylene or polypropylene such as ADMERT"" (trademark of Mitsui Petrochemicals) adhesive resin or ethylene-vinyl acetate copolymer resins such as ELVAXTM (trademark of DuPont).
The adhesives which can be employed in the practice of the present invention for repairing fuel tanks include those adhesives which can support a load of 1334N.
Advantageously, the adhesive has a fuel vapor permeation rate of not more than 46 g-mm/m2/day and, more advantageously, not more than 12 g-mm/m2/day, as determined by ASTM E 96 - 94.
Preferably the adhesives are those which bond to low energy surface plastic materials, such as the adhesive commercially known as LEA and described in an advertisement in the SPE Plastics Engineering magazine, March 2001 page 22;
and adhesives comprising an amine/organoborane complex, such as those described in a series ofpatents issued to Skoultchi (IJS PatentNos. 5,106,928, 5,143,884, 5,286,821, 5,310,835 and 5,376,746). These patents disclose a two-part initiator system that is reportedly usefixl in acrylic adhesive compositions. The first part of the two-part system includes a stable organoborane/amine complex and the second part includes a destabilizer or activator such as an organic acid or an aldehyde. The organoborane compound of the complex has three ligands which can be selected from Cl_io alkyl groups or phenyl groups. Useful amines disclosed include octylamine, 1,6 diaminohexane, diethylamine, dibutylamine, diethylenetriamine, dipropylenediamine, 1,3 propylene diamine, and 1,2 propylene diamine.
Other preferred adhesives which can be employed in the practice of the present invention for repairing fizel tanks include those adhesives disclosed by Zharov et al.
in a series of US Patents (LJS 5,539,070; US 5,690,780; and US 5,691,065), all patents.
These patents describe polymerizable acrylic compositions which are particularly useful as adhesives wherein organoborane/amine complexes are used to initiate cure. The organoboranes used have three ligands attached to the borane atom which are selected from C1_to alkyl groups and phenyl. The amine is an alkanol amine or a diamine where the first amine group can be a primary or secondary amine and the second amine is a primary amine. It is disclosed that these complexes are good for initiating polymerization of an adhesive which bonds to low surface energy substrates.
Pocius in a series of patents (US 5,616,796; US 5,6211,43; US 5,681,910; US
5,686,544; US 5,718,977; and US 5,795,657), discloses amine/organoborane complexes with a variety of amines such as polyoxyalkylene polyamines and polyamines which are the reaction product of diprimary amines and compound having at least two groups which react with a primary amine.
The most preferred adhesive materials which can be employed in the practice of the present invention for repairing fuel tanks comprise a preferred class of an amine/organoborane complex described in copending application U.S. Serial No.
09/466,321, filed December 17, 1999. These adhesives are formulated such that no preparation or pre-treatment of the surfaces to be bonded is required.
The organoborane in the amine/organoborane complex is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
Preferably, the trialkyl borane or alkyl cycloalkyl borane corresponds to Formula 1:
Formula 1 B-~ R2 ) 3 -$-wherein B represents Boron; and R2 is separately in each occurrence a Cl_io alkyl, C3_lo cycloalkyl , or two or more of R2 may combine to form a cycloaliphatic ring.
Preferably Ra is C1~ alkyl, even more preferably C2~ alkyl, and most preferably C3_4 alkyl.
The amine comprises a compound having a primary amine and one or more hydrogen bond accepting groups, wherein there are at least two carbon atoms, preferably at least three, between the primary amine and hydrogen bond accepting groups.
Hydrogen bond accepting group means herein a functional group that through either inter-or intramolecular interaction with a hydrogen of the borane-complexing amine increases the electron density of the nitrogen of the amine group complexing with the borane. Preferred hydrogen bond accepting groups include primary amines, secondary amines, tertiary amines, ethers, halogen, polyethers, and polyamines.
Preferably, the amine corresponds to Formula 2:
NH2 C~H~~C ~R 1)2~X Formula 2 wherein Rl is separately in each occurrence hydrogen or a Ci_io alkyl or C3_lo cycloalkyl; X
is hydrogen bond accepting moiety; a is an integer of 1 to 10; and b is separately in each occurrence an integer of 0 to 1, and the sum of a and b is from 2 to 10.
Preferably Rl is hydrogen or methyl. Preferably X is separately in each occurrence a hydrogen accepting moiety with the proviso that when the hydrogen accepting, moiety is an amine it is a tertiary or a secondary amine. More preferably X is separately in each occurrence N(R$)e, -ORl°, or a halogen wherein R8 is separately in each occurrence Ci_lo alkyl, C3_lo cycloalkyl or -(C(Rl)a)a-W; Rl° is separately in each occurrence, Cl_lo alkyl, C3_io cycloalkyl, or -(C(Rl)a)a-W; and a is 0, 1, or 2. More preferably X is N(R8)~ or -ORl°.
Preferably, Rg and Rl° are C1_4 alkyl or -(C(Rl)2)a-W, more preferably C1~ alkyl and most preferably methyl; W is separately in each occurrence hydrogen or Cl_lo alkyl or X and more preferably hydrogen or Ci_4 alkyl. Preferably, a is 1 or greater and more preferably 2 or greater.
Preferably a is 6 or less, and most preferably 4 or less. Preferably, b is 1. Preferably, the sum of a and b is an integer 2 or greater and most preferably 3 or greater. Preferably the sum of a and b are 6 or less and more preferably 4 or less. Preferably d is separately in each occurrence an integer of 1 to 4, more preferably 2 to 4, and most preferably 2 to 3.
These patents describe polymerizable acrylic compositions which are particularly useful as adhesives wherein organoborane/amine complexes are used to initiate cure. The organoboranes used have three ligands attached to the borane atom which are selected from C1_to alkyl groups and phenyl. The amine is an alkanol amine or a diamine where the first amine group can be a primary or secondary amine and the second amine is a primary amine. It is disclosed that these complexes are good for initiating polymerization of an adhesive which bonds to low surface energy substrates.
Pocius in a series of patents (US 5,616,796; US 5,6211,43; US 5,681,910; US
5,686,544; US 5,718,977; and US 5,795,657), discloses amine/organoborane complexes with a variety of amines such as polyoxyalkylene polyamines and polyamines which are the reaction product of diprimary amines and compound having at least two groups which react with a primary amine.
The most preferred adhesive materials which can be employed in the practice of the present invention for repairing fuel tanks comprise a preferred class of an amine/organoborane complex described in copending application U.S. Serial No.
09/466,321, filed December 17, 1999. These adhesives are formulated such that no preparation or pre-treatment of the surfaces to be bonded is required.
The organoborane in the amine/organoborane complex is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
Preferably, the trialkyl borane or alkyl cycloalkyl borane corresponds to Formula 1:
Formula 1 B-~ R2 ) 3 -$-wherein B represents Boron; and R2 is separately in each occurrence a Cl_io alkyl, C3_lo cycloalkyl , or two or more of R2 may combine to form a cycloaliphatic ring.
Preferably Ra is C1~ alkyl, even more preferably C2~ alkyl, and most preferably C3_4 alkyl.
The amine comprises a compound having a primary amine and one or more hydrogen bond accepting groups, wherein there are at least two carbon atoms, preferably at least three, between the primary amine and hydrogen bond accepting groups.
Hydrogen bond accepting group means herein a functional group that through either inter-or intramolecular interaction with a hydrogen of the borane-complexing amine increases the electron density of the nitrogen of the amine group complexing with the borane. Preferred hydrogen bond accepting groups include primary amines, secondary amines, tertiary amines, ethers, halogen, polyethers, and polyamines.
Preferably, the amine corresponds to Formula 2:
NH2 C~H~~C ~R 1)2~X Formula 2 wherein Rl is separately in each occurrence hydrogen or a Ci_io alkyl or C3_lo cycloalkyl; X
is hydrogen bond accepting moiety; a is an integer of 1 to 10; and b is separately in each occurrence an integer of 0 to 1, and the sum of a and b is from 2 to 10.
Preferably Rl is hydrogen or methyl. Preferably X is separately in each occurrence a hydrogen accepting moiety with the proviso that when the hydrogen accepting, moiety is an amine it is a tertiary or a secondary amine. More preferably X is separately in each occurrence N(R$)e, -ORl°, or a halogen wherein R8 is separately in each occurrence Ci_lo alkyl, C3_lo cycloalkyl or -(C(Rl)a)a-W; Rl° is separately in each occurrence, Cl_lo alkyl, C3_io cycloalkyl, or -(C(Rl)a)a-W; and a is 0, 1, or 2. More preferably X is N(R8)~ or -ORl°.
Preferably, Rg and Rl° are C1_4 alkyl or -(C(Rl)2)a-W, more preferably C1~ alkyl and most preferably methyl; W is separately in each occurrence hydrogen or Cl_lo alkyl or X and more preferably hydrogen or Ci_4 alkyl. Preferably, a is 1 or greater and more preferably 2 or greater.
Preferably a is 6 or less, and most preferably 4 or less. Preferably, b is 1. Preferably, the sum of a and b is an integer 2 or greater and most preferably 3 or greater. Preferably the sum of a and b are 6 or less and more preferably 4 or less. Preferably d is separately in each occurrence an integer of 1 to 4, more preferably 2 to 4, and most preferably 2 to 3.
Among preferred amines corresponding to Formula 2 are dimethylaminopropyl amine, methoxypropyl amine, dimethylaminoethylamine, dimethylaminobutylamine, methoxybutyl amine, methoxyethyl amine, ethoxypropylamine, propoxypropylamine, amine terminated polyalkylene ethers (such as trimethylolpropane tris(poly(propyleneglycol), amine terminated)ether), aminopropylmorpholine, isophoronediamine, and aminopropylpropanediamine.
In one embodiment the preferred amine complex corresponds to Formula 3:
C R2~B ~---NHS ~CH~~C CR 1~2~--J b~ l Formula 3 wherein Rl, RZ, X, a and b are as defined hereinbefore.
In another embodiment the amine is an aliphatic heterocycle having at least one nitrogen in the heterocycle. The heterocyclic compound may also contain one or more of nitrogen, oxygen, sulfur or double bonds.
In addition, the heterocycle may comprise multiple rings wherein at least one of the rings has a nitrogen in the ring. Preferably the aliphatic heterocylic amine corresponds to Formula 4:
3~
X
H y Formula 4 3\
JX
wherein R3 is separately in each occurrence hydrogen, a C1_lo alkyl or C3_lo cycloalkyl; Z is separately in each occurrence oxygen or NR4 wherein R4 is hydrogen, Cl_lo alkyl, or C 6_io aryl or alkaryl; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x should be from 2 to 10; and y is separately in each occurrence 0 or 1. Preferably, R3 is separately in each occurrence hydrogen or methyl.
Preferably Z is NR4. Preferably, R4 is hydrogen or Cl~ alkyl, and more preferably hydrogen or methyl. Preferably x is from 1 to 5 and the total of all the occurrences of x is 3 to 5. Preferred compounds corresponding to Formula 4 include morpholine, piperidine, pyrolidine, piperazine,1,3,3 trimethyl 6-azabicyclo[3,2,1] octane, thiazolidine, homopiperazine, aziridine, 1,4-diazabicylo[2.2.2]octane (DABCO), 1-amino-4-methylpiperazine, and 3-pyrroline. Complexes using aliphatic heterocyclic amines preferably correspond to Formula 5:
3\
v JX
c R2~--B
Formula 5 3\
JX
wherein R2, R3, Z, x and y are as defined hereinbefore.
In yet another embodiment, the amine which is complexed with the organoborane is an amidine. Any compound with amidine structure wherein the amidine has sufficient binding energy as described hereinbefore with the organoborane, may be used. Preferable amidine compounds correspond to Formula 6:
R~ /hT(RS J 2 C
Formula 6 \ R7 wherein R5, R6, and R~ are separately in each occurrence hydrogen, a C1_lo alkyl or C3_io cycloalkyl; two or more of R5, R6, and R' may combine in any combination to form a ring structure, which may have one or more rings. Preferably R5, R6 and R' are separately in each occurrence hydrogen, Cl~. alkyl or CS_6 cycloalkyl. Most preferably R' is H or methyl.
In the embodiment where two or more of R5, R6 and R' combine to form a ring structure the ring structure is preferably a single or a double ring structure. Among preferred amidines are I,8 diazabicyclo[5,4lundec-7-ene; tetrahydropyrimidine; 2-methyl-2-imidazoline; and 1,1,3,3-tetramethylguanidine.
The organoborane amidine complexes preferably correspond to Formula 7:
Formula 7 R~ /N(Rs ~ 2 C
C R~~ B E-- N~
_g_ wherein R2, R5, R6 and R' are as defined earlier.
In yet another embodiment, the amine which is complexed with the organoborane is a conjugated imine. Any compound with a conjugated imine structure, wherein the imine has sufficient binding energy as described hereinbefore with the organoborane, rnay be used. The conjugated imine can be a straight or branched chain imine or a cylic imine. Preferable imine compounds correspond to Formula 8:
NR~ CR9 ~ CR9 CR9 ~ c Y Formula 8 wherein Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, halogen or an alkylene group which forms a cyclic ring with an R~ or R9. R4 is hydrogen, C1_lo alkyl, or C 6_1o aryl or alkaryl. Preferably R4 is hydrogen or methyl. R' is as described previously. R9 is independently in each occurrence hydrogen, Y, C1_lo alkyl, C3_lo cycloalkyl-, (C(R9)2-(CRg=CR9)~ Y or two or more of R9 can combine to form a ring structure provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; and c is an integer of from 1 to 10. Preferably, R9 is hydrogen or methyl.
Y is preferably N(R4)Z, or OR4, or an alkylene group which forms a cyclic ring with R~ or Rg.
Y is more preferably N(R4)a or an alkylene group which forms a cyclic ring with R' or R9. Preferably, c is an integer of from 1 to 5, and most preferably 1. Among preferred conjugated imines useful in this invention are 4-dimethylaminopyridine; 2,3-bis(dimethylamino)cyclopropeneimine;(dimethylamine)acroleinimine; and 3-(dimethylamino)methacroleinimine.
Among preferred cyclic imines are those corresponding to the following structures:
N I N R
R9 w R9 1 9 R9 \R9 The complexes with the conjugated imines preferably correspond to Formula 9:
C rt2~BE NR~ CR9 ~ CR9 CR9 ~ c Formula 9 wherein R2, R', R9, c and Y are as defined hereinbefore.
The molar ratio of amine compound to borane compound in the complex is relatively important., In some complexes if the molar ratio of amine compound to organoborane compound is too low, the complex is pyrophoric. Preferably the molar ratio of amine compound to organoborane compound is from 1.0:1.0 to 3.0:1Ø Below the ratio of 1.0:1.0 there may be problems with polymerization, stability of the complex and for adhesive uses, adhesion. Crreater than a 3.0:1.0 ratio may be used although there is no benefit from using a ratio greater than 3.0:1Ø If too much amine is present, this may negatively impact the stability of the adhesive or polymer compositions.
Preferably the molar ratio of amine compound to organoborane compound is from 2.0:1.0 to 1.0:1Ø
The polymerizable compounds which may be used in the polymerization compositions of the adhesive include acrylate and/or methacrylate based compounds, with methylinethacrylate, butylmethacrylate, 2-ethylhexylmethacrylate, isobornylmethacrylate, tetrahydrofurfuryl methacrylate, and cyclohexylmethylmethacrylate as the most preferred.
Adhesives which do not bond to low energy surface materials can be used also in the practice of the present invention. These adhesives require pretreatment of the surfaces of the materials to be joined. Such adhesives, include, for example, polyurethane-, epoxy-, polyimide-, phenolic/resorcinolic-, or acrylate-based adhesives.
Surface pretreatments of metals include, for example, phosphate conversion coating, passivation, pickling, grit-blasting, various plasma treatments, for example oxygen, helium, argon, air, nitrous oxide, carbon dioxide, nitrogen, and ammonia;
flame-carried silane (Pyrosil~), sandpaper delivered silicate, various solvent soaks and wipes, abrading, alkali cleaning, silane-based primers, peel ply and artificial surface coatings, that is e-coat.
Surface pretreatments of plastics include, for example, etching, aluminum-alkali and electrochemical treatments, solvent cleaning, flame treatments, chemical treatments, plasma treatments, artificial coatings, UV irradiation and photochemical treatments.
The adhesive can be applied to the detected leaks, fuel tank surface with detected leaks or to the patch surface with the aid of customary methods, for example, by spraying, knife coating, dipping or brushing.
Referring now to Figs. la and 1b, there is shown HDPE fuel tank 10 with a crack puncture 13. Disposed directly over crack/puncture 13 is a plastic patch or plug 21 attached to the surface immediately surrounding crack/puncture 13 by adhesive 12.
Adhesive 12 comprises the most preferred adhesive as described previously.
In Fig.lb, there is shown stand off 14 which limits the compression of adhesive 12.
Shown in Figures 2a, 2b and 2c is an example of the use of a patch or plug after fuel contamination of the exterior surface of a fuel tank. The crack/puncture 23 is cut out to a diameter that would exceed fuel contamination of the outer substrate.
Patch or plug 21 is applied over the crack or puncture. Patch or plug 21 is attached to the fuel tank 20 by adhesive 22. In Fig. 2, there is shown tank outer substrate 34 and its portion 34' contaminated with fuel. The contaminated portion 24' is cut out as shown in Fig. 2B and patch 21 is placed over tank 20 as shown to cover the hole left by the cut out contaminated portion 24'. Patch 21 is attached to the tank by adhesive 22. In Fig. 2C, patch 21 is provided with snapfit 23. Snap fit 23 and/or an interference fit, or other mechanical attachment, such as, for example, a clip, clamp or nut and bolt, is used to temporarily hold the patch and the tank surface together while adhesive 22 cures to an acceptable green strength.
In one embodiment the preferred amine complex corresponds to Formula 3:
C R2~B ~---NHS ~CH~~C CR 1~2~--J b~ l Formula 3 wherein Rl, RZ, X, a and b are as defined hereinbefore.
In another embodiment the amine is an aliphatic heterocycle having at least one nitrogen in the heterocycle. The heterocyclic compound may also contain one or more of nitrogen, oxygen, sulfur or double bonds.
In addition, the heterocycle may comprise multiple rings wherein at least one of the rings has a nitrogen in the ring. Preferably the aliphatic heterocylic amine corresponds to Formula 4:
3~
X
H y Formula 4 3\
JX
wherein R3 is separately in each occurrence hydrogen, a C1_lo alkyl or C3_lo cycloalkyl; Z is separately in each occurrence oxygen or NR4 wherein R4 is hydrogen, Cl_lo alkyl, or C 6_io aryl or alkaryl; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x should be from 2 to 10; and y is separately in each occurrence 0 or 1. Preferably, R3 is separately in each occurrence hydrogen or methyl.
Preferably Z is NR4. Preferably, R4 is hydrogen or Cl~ alkyl, and more preferably hydrogen or methyl. Preferably x is from 1 to 5 and the total of all the occurrences of x is 3 to 5. Preferred compounds corresponding to Formula 4 include morpholine, piperidine, pyrolidine, piperazine,1,3,3 trimethyl 6-azabicyclo[3,2,1] octane, thiazolidine, homopiperazine, aziridine, 1,4-diazabicylo[2.2.2]octane (DABCO), 1-amino-4-methylpiperazine, and 3-pyrroline. Complexes using aliphatic heterocyclic amines preferably correspond to Formula 5:
3\
v JX
c R2~--B
Formula 5 3\
JX
wherein R2, R3, Z, x and y are as defined hereinbefore.
In yet another embodiment, the amine which is complexed with the organoborane is an amidine. Any compound with amidine structure wherein the amidine has sufficient binding energy as described hereinbefore with the organoborane, may be used. Preferable amidine compounds correspond to Formula 6:
R~ /hT(RS J 2 C
Formula 6 \ R7 wherein R5, R6, and R~ are separately in each occurrence hydrogen, a C1_lo alkyl or C3_io cycloalkyl; two or more of R5, R6, and R' may combine in any combination to form a ring structure, which may have one or more rings. Preferably R5, R6 and R' are separately in each occurrence hydrogen, Cl~. alkyl or CS_6 cycloalkyl. Most preferably R' is H or methyl.
In the embodiment where two or more of R5, R6 and R' combine to form a ring structure the ring structure is preferably a single or a double ring structure. Among preferred amidines are I,8 diazabicyclo[5,4lundec-7-ene; tetrahydropyrimidine; 2-methyl-2-imidazoline; and 1,1,3,3-tetramethylguanidine.
The organoborane amidine complexes preferably correspond to Formula 7:
Formula 7 R~ /N(Rs ~ 2 C
C R~~ B E-- N~
_g_ wherein R2, R5, R6 and R' are as defined earlier.
In yet another embodiment, the amine which is complexed with the organoborane is a conjugated imine. Any compound with a conjugated imine structure, wherein the imine has sufficient binding energy as described hereinbefore with the organoborane, rnay be used. The conjugated imine can be a straight or branched chain imine or a cylic imine. Preferable imine compounds correspond to Formula 8:
NR~ CR9 ~ CR9 CR9 ~ c Y Formula 8 wherein Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, halogen or an alkylene group which forms a cyclic ring with an R~ or R9. R4 is hydrogen, C1_lo alkyl, or C 6_1o aryl or alkaryl. Preferably R4 is hydrogen or methyl. R' is as described previously. R9 is independently in each occurrence hydrogen, Y, C1_lo alkyl, C3_lo cycloalkyl-, (C(R9)2-(CRg=CR9)~ Y or two or more of R9 can combine to form a ring structure provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; and c is an integer of from 1 to 10. Preferably, R9 is hydrogen or methyl.
Y is preferably N(R4)Z, or OR4, or an alkylene group which forms a cyclic ring with R~ or Rg.
Y is more preferably N(R4)a or an alkylene group which forms a cyclic ring with R' or R9. Preferably, c is an integer of from 1 to 5, and most preferably 1. Among preferred conjugated imines useful in this invention are 4-dimethylaminopyridine; 2,3-bis(dimethylamino)cyclopropeneimine;(dimethylamine)acroleinimine; and 3-(dimethylamino)methacroleinimine.
Among preferred cyclic imines are those corresponding to the following structures:
N I N R
R9 w R9 1 9 R9 \R9 The complexes with the conjugated imines preferably correspond to Formula 9:
C rt2~BE NR~ CR9 ~ CR9 CR9 ~ c Formula 9 wherein R2, R', R9, c and Y are as defined hereinbefore.
The molar ratio of amine compound to borane compound in the complex is relatively important., In some complexes if the molar ratio of amine compound to organoborane compound is too low, the complex is pyrophoric. Preferably the molar ratio of amine compound to organoborane compound is from 1.0:1.0 to 3.0:1Ø Below the ratio of 1.0:1.0 there may be problems with polymerization, stability of the complex and for adhesive uses, adhesion. Crreater than a 3.0:1.0 ratio may be used although there is no benefit from using a ratio greater than 3.0:1Ø If too much amine is present, this may negatively impact the stability of the adhesive or polymer compositions.
Preferably the molar ratio of amine compound to organoborane compound is from 2.0:1.0 to 1.0:1Ø
The polymerizable compounds which may be used in the polymerization compositions of the adhesive include acrylate and/or methacrylate based compounds, with methylinethacrylate, butylmethacrylate, 2-ethylhexylmethacrylate, isobornylmethacrylate, tetrahydrofurfuryl methacrylate, and cyclohexylmethylmethacrylate as the most preferred.
Adhesives which do not bond to low energy surface materials can be used also in the practice of the present invention. These adhesives require pretreatment of the surfaces of the materials to be joined. Such adhesives, include, for example, polyurethane-, epoxy-, polyimide-, phenolic/resorcinolic-, or acrylate-based adhesives.
Surface pretreatments of metals include, for example, phosphate conversion coating, passivation, pickling, grit-blasting, various plasma treatments, for example oxygen, helium, argon, air, nitrous oxide, carbon dioxide, nitrogen, and ammonia;
flame-carried silane (Pyrosil~), sandpaper delivered silicate, various solvent soaks and wipes, abrading, alkali cleaning, silane-based primers, peel ply and artificial surface coatings, that is e-coat.
Surface pretreatments of plastics include, for example, etching, aluminum-alkali and electrochemical treatments, solvent cleaning, flame treatments, chemical treatments, plasma treatments, artificial coatings, UV irradiation and photochemical treatments.
The adhesive can be applied to the detected leaks, fuel tank surface with detected leaks or to the patch surface with the aid of customary methods, for example, by spraying, knife coating, dipping or brushing.
Referring now to Figs. la and 1b, there is shown HDPE fuel tank 10 with a crack puncture 13. Disposed directly over crack/puncture 13 is a plastic patch or plug 21 attached to the surface immediately surrounding crack/puncture 13 by adhesive 12.
Adhesive 12 comprises the most preferred adhesive as described previously.
In Fig.lb, there is shown stand off 14 which limits the compression of adhesive 12.
Shown in Figures 2a, 2b and 2c is an example of the use of a patch or plug after fuel contamination of the exterior surface of a fuel tank. The crack/puncture 23 is cut out to a diameter that would exceed fuel contamination of the outer substrate.
Patch or plug 21 is applied over the crack or puncture. Patch or plug 21 is attached to the fuel tank 20 by adhesive 22. In Fig. 2, there is shown tank outer substrate 34 and its portion 34' contaminated with fuel. The contaminated portion 24' is cut out as shown in Fig. 2B and patch 21 is placed over tank 20 as shown to cover the hole left by the cut out contaminated portion 24'. Patch 21 is attached to the tank by adhesive 22. In Fig. 2C, patch 21 is provided with snapfit 23. Snap fit 23 and/or an interference fit, or other mechanical attachment, such as, for example, a clip, clamp or nut and bolt, is used to temporarily hold the patch and the tank surface together while adhesive 22 cures to an acceptable green strength.
Claims (15)
1. A method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, filling the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks.
2. The method of Claim 1 wherein the adhesive comprises an amine/organoborane complex.
3. The method of Claim 2 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
and (4) conjugated imines.
4. The method of Claim 3 wherein the complex of the organoborane and the primary amine corresponds to the formula the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula ~
and the organoborane conjugated imine complex corresponds to the formula wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl or alkaryl; R5, R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
and the organoborane conjugated imine complex corresponds to the formula wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl or alkaryl; R5, R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
5. The method of Claim 2 wherein the organo borane/amine complex comprises an aliphatic heterocylic amine which is a five or six membered heterocylic compound.
6. The method of Claim 2 wherein the organo borane compound of the complex has three ligands selected from C1-10 alkyl groups or phenyl groups, and the amine compound is selected from 1,6 diaminohexane, diethylamine, dibutylamine, diethylenetriamine, dipropylenediamine, 1,3 propylene diamine, and 1,2 propylene diamine.
7. The method of Claim 2 wherein the organoborane compound of the complex has three ligands attached to the borane atom and which are selected from C1_m alkyl groups and phenyl and the amine compound is an alkanol amine or a diamine wherein the first amine group is a primary or secondary amine and the second amine is a primary amine.
8. The method of Claim 2 wherein the amine compound of the complex is a polyoxyalkylene polyamine or a polyamine which is the reaction product of a diprimary amine and a compound having at least two groups which react with a primary amine.
9. The method of Claim 1 wherein the fuel tank is made of stainless steel, pre-coated or post-coated low-carbon steel, aluminum, bronze, electroplated zinc, nickel or galvanneal.
10. The method of Claim 1 wherein the fuel tank is made of metal or a multilayer structure having one or more layers of a polymer having fuel barrier property and one or more layers of a low energy surface material.
11. The method of Claim 10 wherein the low energy surface material is high density polyethylene and the fuel barrier polymer is selected from the group consisting of polyamides, fluoroelastomers, polyacetal homopolymers and copolymers, sulfonated and fluorinated HDPE, ethylene vinyl alcohol polymers and copolymers, hydroxy-functionalized polyethers and polyesters, and branched polyesters.
12. The method of Claim 1 wherein the adhesive comprises an adhesive having fuel barrier property and which bonds to low energy surface materials.
13. The method of Claim 12 wherein the adhesive comprises an amine/organoborane complex.
14. The method of Claim 13 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
15. The method of Claim 14 wherein the complex of the organoborane and the primary amine corresponds to the formula the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl or alkaryl; R5 , R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y
or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
16. The method of Claim 14 wherein the organo borane/amine complex comprises an aliphatic heterocylic amine which is a five or six membered heterocylic compound.
17. The method of Claim 13 wherein the organo borane compound of the complex has three ligands selected from C1-10 alkyl groups or phenyl groups, and the amine compound is selected from 1,6 diaminohexane, diethylamine, dibutylamine, diethylenetriamine, dipropylenediamine, 1,3 propylene diamine, and 1,2 propylene diamine.
18. The method of Claim 13 wherein the organoborane compound of the complex has three ligands attached to the borane atom and which are selected from C1-10 alkyl groups and phenyl and the amine compound is an alkanol amine or a diamine wherein the first amine group is a primary or secondary amine and the second amine is a primary amine.
19. The method of Claim 13 wherein the amine compound of the complex is a polyoxyalkylene polyamine or a polyamine which is the reaction product of a diprimary amine and a compound having at least two groups which react with a primary amine.
20. The method of Claim 1 wherein the fuel tank is made of metal or a monolayer or multilayer plastic.
21. The method of Claim 1 wherein the adhesive comprises a polyurethane-, epoxy-, polyimide-, phenolic/resorcinolic-, or acrylate-based adhesive.
22. The method of Claim 1 wherein the fuel tank surface is cleaned and/or pre-treated to provide adequate bonding between the adhesive and the fuel tank.
23. The method of Claim 22 wherein the exterior and/or interior surface of the fuel tank is cleaned with water and or soap, or solvent.
24. The method of Claim 22 wherein the exterior and/or interior surface of the fuel tank is sanded or sandblasted.
25. A method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, providing a patch or plug having a surface to be attached to the fuel tank surface with detected leaks, coating the tank surface and/or the patch or plug surface with an adhesive, placing the patch or plug over the detected leaks) such that the adhesive is sandwiched between the patch or plug surface and the tank surface, pressing the patch or plug against the tank and allowing the adhesive to cure to bond together the patch or plug surface and the tank surface.
26. The method of Claim 25 wherein the patch is made of woven or non-woven fabric, a composite material or a monolayer or multilayer plastic laminate.
WHAT IS CLAIMED IS:
1. A method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, filling the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks.
2. The method of Claim 1 wherein the adhesive comprises an amine/organoborane complex.
3. The method of Claim 2 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
4. The method of Claim 3 wherein the complex of the organoborane and the primary amine corresponds to the formula the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula (R2~B.rarw.NR7~CR9~(R9~CR9~Y;
wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C 6-10 aryl or alkaryl;
R5, R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y
or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
14. The method of Claim 13 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
15. The method of Claim 14 wherein the complex of the organoborane and the primary amine corresponds to the formula the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl or alkaryl; R5 , R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y
or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
16. The method of Claim 14 wherein the organo borane/amine complex comprises an aliphatic heterocylic amine which is a five or six membered heterocylic compound.
17. The method of Claim 13 wherein the organo borane compound of the complex has three ligands selected from C1-10 alkyl groups or phenyl groups, and the amine compound is selected from 1,6 diaminohexane, diethylamine, dibutylamine, diethylenetriamine, dipropylenediamine, 1,3 propylene diamine, and 1,2 propylene diamine.
18. The method of Claim 13 wherein the organoborane compound of the complex has three ligands attached to the borane atom and which are selected from C1-10 alkyl groups and phenyl and the amine compound is an alkanol amine or a diamine wherein the first amine group is a primary or secondary amine and the second amine is a primary amine.
19. The method of Claim 13 wherein the amine compound of the complex is a polyoxyalkylene polyamine or a polyamine which is the reaction product of a diprimary amine and a compound having at least two groups which react with a primary amine.
20. The method of Claim 1 wherein the fuel tank is made of metal or a monolayer or multilayer plastic.
21. The method of Claim 1 wherein the adhesive comprises a polyurethane-, epoxy-, polyimide-, phenolic/resorcinolic-, or acrylate-based adhesive.
22. The method of Claim 1 wherein the fuel tank surface is cleaned and/or pre-treated to provide adequate bonding between the adhesive and the fuel tank.
23. The method of Claim 22 wherein the exterior and/or interior surface of the fuel tank is cleaned with water and or soap, or solvent.
24. The method of Claim 22 wherein the exterior and/or interior surface of the fuel tank is sanded or sandblasted.
25. A method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, providing a patch or plug having a surface to be attached to the fuel tank surface with detected leaks, coating the tank surface and/or the patch or plug surface with an adhesive, placing the patch or plug over the detected leaks) such that the adhesive is sandwiched between the patch or plug surface and the tank surface, pressing the patch or plug against the tank and allowing the adhesive to cure to bond together the patch or plug surface and the tank surface.
26. The method of Claim 25 wherein the patch is made of woven or non-woven fabric, a composite material or a monolayer or multilayer plastic laminate.
WHAT IS CLAIMED IS:
1. A method for repairing fuel tanks which comprises providing a fuel tank having a surface with detected leaks, filling the detected leaks by applying an adhesive over the detected leaks and allowing the adhesive to cure to seal the detected leaks.
2. The method of Claim 1 wherein the adhesive comprises an amine/organoborane complex.
3. The method of Claim 2 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
4. The method of Claim 3 wherein the complex of the organoborane and the primary amine corresponds to the formula the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula (R2~B.rarw.NR7~CR9~(R9~CR9~Y;
wherein B is boron; R1 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R2 is separately in each occurrence a C1-10 alkyl, C3-10 cycloalkyl or two or more of R2 may combine to form a cycloaliphatic ring structure; R3 is separately in each occurrence hydrogen, a C1-10 alkyl or C3-10 cycloalkyl; R4 is separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C 6-10 aryl or alkaryl;
R5, R6, and R7 are separately in each occurrence hydrogen, C1-10 alkyl, C3-10 cycloalkyl, or two or more of R5, R6 and R7 in any combination can combine to form a ring structure which can be a single ring or a multiple ring structure and the ring structure can include one or more of nitrogen, oxygen or unsaturation in the ring structure; R9 is independently in each occurrence hydrogen, C1-10 alkyl or C3-10 cycloalkyl, Y, -(C(R9)2-(CR9=CR9)c-Y
or two or more of R9 can combine to form a ring structure, or one or more of R9 can form a ring structure with Y provided the ring structure is conjugated with respect to the double bond of the imine nitrogen; X is a hydrogen-bond accepting group with the proviso that where the hydrogen bond accepting group is an amine it must be secondary or tertiary;
Y is independently in each occurrence hydrogen, N(R4)2, OR4, C(O)OR4, a halogen or an alkylene group which forms a cyclic ring with R7 or R9; Z is separately in each occurrence oxygen or NR4; a is separately in each occurrence an integer of from 1 to 10; b is separately in each occurrence 0 or 1, with the proviso that the sum of a and b should be from 2 to 10; c is separately in each occurrence an integer of from 1 to 10; x is separately in each occurrence an integer of 1 to 10, with the proviso that the total of all occurrences of x is from 2 to 10; and y is separately in each occurrence 0 or 1.
14. The method of Claim 13 wherein the organoborane is a trialkyl borane or alkyl cycloalkyl borane and the amine is selected from the group consisting of (1) amines having an amidine structural component; (2) aliphatic heterocycles having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; (3) primary amines which in addition have one or more hydrogen bond accepting groups wherein there are at least two carbon atoms, preferably at least three carbon atoms, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B-N bond is increased;
and (4) conjugated imines.
and (4) conjugated imines.
15. The method of Claim 14 wherein the complex of the organoborane and the primary amine corresponds to the formula (R2~B .rarw.NH2(CH2~C(R1)2~X ;
the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula (R2~B.rarw.NR7~CR9~(CR9~CR9~Y;
the organoborane heterocyclic amine complex corresponds to the formula the organoborane amidine complex corresponds to the formula and the organoborane conjugated imine complex corresponds to the formula (R2~B.rarw.NR7~CR9~(CR9~CR9~Y;
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/935,900 | 2001-08-23 | ||
US09/935,900 US20030047268A1 (en) | 2001-08-23 | 2001-08-23 | Method for repairing fuel tanks |
PCT/US2002/026700 WO2003018705A1 (en) | 2001-08-23 | 2002-08-21 | Method for repairing fuel tanks |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2456556A1 true CA2456556A1 (en) | 2003-03-06 |
Family
ID=25467863
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002456556A Abandoned CA2456556A1 (en) | 2001-08-23 | 2002-08-21 | Method for repairing fuel tanks |
Country Status (8)
Country | Link |
---|---|
US (2) | US20030047268A1 (en) |
EP (1) | EP1421149A1 (en) |
JP (1) | JP2005511414A (en) |
KR (1) | KR20040027987A (en) |
CN (1) | CN1545543A (en) |
BR (1) | BR0212568A (en) |
CA (1) | CA2456556A1 (en) |
WO (1) | WO2003018705A1 (en) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1201722A1 (en) * | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
IE20020293A1 (en) * | 2002-04-23 | 2003-10-29 | Loctite R & D Ltd | Initiator systems, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
WO2003089536A2 (en) * | 2002-04-19 | 2003-10-30 | Loctite (R & D) Limited | Polymerisation initiators based on ammonium tetraalkyl boranes, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
US7098279B2 (en) * | 2002-10-22 | 2006-08-29 | Loctite (R&D) Limited | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
US7341285B2 (en) | 2004-03-24 | 2008-03-11 | Ips Corporation Weld-On Division | Chemical fusion of non-metallic pipe joints |
US8746747B2 (en) | 2004-03-24 | 2014-06-10 | IPS Corporation—Weld-On Division | Pipe joints |
DE102004018047A1 (en) * | 2004-04-08 | 2005-11-10 | Tesa Ag | Process for permanently closing holes, in particular in metal sheets or in plastic parts of automobile bodies |
US7360552B2 (en) * | 2004-04-23 | 2008-04-22 | Dow Global Technologies Inc. | Injectable structural adhesive |
FR2874019B1 (en) * | 2004-08-04 | 2006-11-10 | Electricite De France | AUTOMATED METHOD FOR IN SITU REPAIR OF A ZONE WHICH CAN INCLUDE FISSURE ON THE SURFACE OF AN ENCLOSURE |
FR2874020B1 (en) * | 2004-08-04 | 2006-12-08 | Electricite De France | METHOD FOR IN SITU REPAIR OF A ZONE WHICH CAN INCLUDE FISSURE ON THE SURFACE OF AN ENCLOSURE |
DE102004055324A1 (en) * | 2004-11-16 | 2006-05-18 | Tesa Ag | Punch for permanent sealing of holes, especially in sheet metal or in plastic parts of car bodies |
US8202932B2 (en) * | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
US7408012B1 (en) | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
US7297364B2 (en) | 2005-12-19 | 2007-11-20 | The Magni Group, Inc. | Method for refurbishing lamp surfaces |
US9987025B2 (en) * | 2006-05-26 | 2018-06-05 | Bruce B. Becker | Increased axial load carrying sheathed irrigating balloon catheter |
DE102006038322A1 (en) * | 2006-08-15 | 2008-02-21 | Tesa Ag | Punching in particular for the permanent closing of holes |
US7896568B2 (en) * | 2008-03-05 | 2011-03-01 | Richard Warren Atkinson | Articulite |
US9017499B2 (en) * | 2008-12-05 | 2015-04-28 | The Boeing Company | Bonded patches with bond line control |
US8734604B2 (en) * | 2008-12-05 | 2014-05-27 | The Boeing Company | Bond line control process |
US10022922B2 (en) | 2008-12-05 | 2018-07-17 | The Boeing Company | Bonded patches with bond line control |
US8795455B2 (en) * | 2008-12-05 | 2014-08-05 | The Boeing Company | Bonded patches with bond line control |
US9492975B2 (en) | 2009-03-09 | 2016-11-15 | The Boeing Company | Structural bonded patch with tapered adhesive design |
US8524356B1 (en) | 2009-03-09 | 2013-09-03 | The Boeing Company | Bonded patch having multiple zones of fracture toughness |
US8617694B1 (en) | 2009-03-09 | 2013-12-31 | The Boeing Company | Discretely tailored multi-zone bondline for fail-safe structural repair |
US8540909B2 (en) * | 2009-03-09 | 2013-09-24 | The Boeing Company | Method of reworking an area of a composite structure containing an inconsistency |
US8449703B2 (en) | 2009-03-09 | 2013-05-28 | The Boeing Company | Predictable bonded rework of composite structures using tailored patches |
US8468709B2 (en) | 2010-11-04 | 2013-06-25 | The Boeing Company | Quick composite repair template tool and method |
CN103727230B (en) * | 2012-10-10 | 2016-05-11 | 李华容 | A kind of method of can seam sealing |
CN103031069B (en) * | 2012-12-20 | 2014-10-15 | 中航通飞华南飞机工业有限公司 | Connecting method of transparent part and composite frame |
US9757898B2 (en) | 2014-08-18 | 2017-09-12 | Lord Corporation | Method for low temperature bonding of elastomers |
JP5739576B1 (en) * | 2014-10-07 | 2015-06-24 | 鈴木 英雄 | Integrated puncture repair material |
JP6261534B2 (en) * | 2015-03-11 | 2018-01-17 | 株式会社神鋼環境ソリューション | Steel plate digestion tank repair method |
US10422428B2 (en) | 2015-04-01 | 2019-09-24 | The Boeing Company | Self-forming fuel tank sealant system |
CN105670522A (en) * | 2016-04-22 | 2016-06-15 | 山西平阳重工机械有限责任公司 | Complex thin-wall partitioned bin sealing and bonding method |
KR101842579B1 (en) * | 2017-03-17 | 2018-03-27 | 포항공과대학교 산학협력단 | Stave |
FR3114817B1 (en) * | 2020-10-02 | 2022-08-26 | Bouygues Energies & Services | Method for repairing a leak at the bottom of a container comprising a reversible sealing of the leak |
Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU34020A1 (en) * | 1953-01-27 | 1956-02-06 | ||
US2993876A (en) * | 1957-04-22 | 1961-07-25 | Phillips Petroleum Co | Ethylene polymer-polyisobutylene composition, method of making same, and electrical wire coated therewith |
US3250825A (en) * | 1962-11-09 | 1966-05-10 | Phillips Petroleum Co | Blends of crystalline polyethylene or ethylene-butene copolymer with amorphous ethylene-higher alpha-olefin copolymers |
US3251461A (en) * | 1963-10-01 | 1966-05-17 | Permanent Tank Bottom Company | Tank repair mechanism |
US3556831A (en) * | 1969-09-16 | 1971-01-19 | Rainer Schinabeck | Method for sealing leaks in pressurized vessels |
US4058234A (en) * | 1975-05-29 | 1977-11-15 | The United States Of America As Represented By The Administrator, Environmental Protection Agency | System for sealing and repairing leaks in ruptured containers |
US4160465A (en) * | 1977-04-19 | 1979-07-10 | Hsu Charles J | Emergency water leak plug |
US4204050A (en) * | 1978-11-09 | 1980-05-20 | The Dow Chemical Company | Polymerization of α-olefins with a dual transition metal catalyst |
FR2453204A1 (en) * | 1979-04-06 | 1980-10-31 | Aerospatiale | SEALING METHOD BASED ON LOADED EPOXY RESIN, PARTICULARLY FOR FUEL TANK |
DE3017632A1 (en) * | 1980-05-08 | 1981-11-12 | Robert Edmund 6634 Wallerfangen Kornbrust | Sealing leak in pressurised pipe - polyester is applied to edge of sand-blasted strip on seal round leak |
US4405048A (en) * | 1982-02-25 | 1983-09-20 | Peake Gilbert R | Fuel tank drain kit and process |
US4574971A (en) * | 1984-12-24 | 1986-03-11 | Leonard Clayborn T | Sealing assembly for vessels |
SU1523565A1 (en) * | 1987-10-06 | 1989-11-23 | В.Н.Николаев и И.В.Николаев | Adhesive composition |
US5272236A (en) * | 1991-10-15 | 1993-12-21 | The Dow Chemical Company | Elastic substantially linear olefin polymers |
US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
US5143884A (en) * | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
US5166007A (en) * | 1991-09-11 | 1992-11-24 | Smith W Novis | Repair compositions and structure |
US5278272A (en) * | 1991-10-15 | 1994-01-11 | The Dow Chemical Company | Elastic substantialy linear olefin polymers |
US5286821A (en) * | 1992-03-17 | 1994-02-15 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
US5458258A (en) * | 1993-09-02 | 1995-10-17 | The Dow Chemical Company | Storage tanks for compressed natural gas with a hydroxy-phenoxyether polymer barrier liner |
US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
CN1054136C (en) * | 1994-02-22 | 2000-07-05 | 美国3M公司 | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
US5928745A (en) * | 1994-06-23 | 1999-07-27 | Cellresin Technologies, Llc | Thermoplastic fuel tank having reduced fuel vapor emissions |
US5690780A (en) * | 1995-02-22 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
US5616796A (en) * | 1995-04-14 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive composition made therewith |
US5621143A (en) * | 1995-04-14 | 1997-04-15 | Minnesota Mining And Manufacturing Company | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
US5686544A (en) * | 1995-08-11 | 1997-11-11 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
CA2236939A1 (en) * | 1995-11-07 | 1997-05-15 | E. John Deviny | Initiator system and adhesive composition made therewith |
JPH09165438A (en) * | 1995-12-18 | 1997-06-24 | Teijin Meton Kk | Method repairing molded article of crosslinked polymer |
US6102641A (en) * | 1998-10-14 | 2000-08-15 | Hildebrandt; David J. | Hole plug |
US6252023B1 (en) * | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
US6806330B1 (en) * | 1999-12-17 | 2004-10-19 | Dow Global Technologies Inc. | Amine organoborane complex polymerization initiators and polymerizable compositions |
-
2001
- 2001-08-23 US US09/935,900 patent/US20030047268A1/en not_active Abandoned
-
2002
- 2002-08-21 CA CA002456556A patent/CA2456556A1/en not_active Abandoned
- 2002-08-21 JP JP2003523557A patent/JP2005511414A/en active Pending
- 2002-08-21 WO PCT/US2002/026700 patent/WO2003018705A1/en not_active Application Discontinuation
- 2002-08-21 CN CNA028162943A patent/CN1545543A/en active Pending
- 2002-08-21 BR BR0212568-4A patent/BR0212568A/en not_active IP Right Cessation
- 2002-08-21 EP EP02750492A patent/EP1421149A1/en not_active Withdrawn
- 2002-08-21 KR KR10-2004-7002610A patent/KR20040027987A/en not_active Application Discontinuation
-
2004
- 2004-08-31 US US10/930,237 patent/US20050022923A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP1421149A1 (en) | 2004-05-26 |
CN1545543A (en) | 2004-11-10 |
KR20040027987A (en) | 2004-04-01 |
US20030047268A1 (en) | 2003-03-13 |
JP2005511414A (en) | 2005-04-28 |
US20050022923A1 (en) | 2005-02-03 |
BR0212568A (en) | 2004-10-13 |
WO2003018705A1 (en) | 2003-03-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2456556A1 (en) | Method for repairing fuel tanks | |
EP1923254A2 (en) | Fuel tank and fuel tank component | |
JP5520830B2 (en) | How to make the joint | |
US20090173441A1 (en) | Method for joining piping systems and piping to equipment, fixtures, devices, structures, and appliances | |
US20020195453A1 (en) | Fuel tanks and fuel transport lines | |
CA2450647A1 (en) | Automobile assembly | |
US20130333838A1 (en) | Low temperature curable epoxy tape and method of making same | |
CN1181102A (en) | Melt-flowable materials and method of sealing surfaces | |
CN113710763B (en) | Elastic single component structural adhesive tape | |
CN101080473A (en) | Adhesive articles comprising fibrous webs | |
KR20070073832A (en) | Method of primerless bonding | |
US20160184943A1 (en) | Method for fabricating vacuum fixturing using granular media | |
US20050145632A1 (en) | Lined container for curable liquid materials | |
US20090090454A1 (en) | Method for joining piping systems and piping to equipment, fixtures, devices, structures, and appliances | |
US4824726A (en) | Layered patching composition | |
CN105636767A (en) | Aircraft water tank and manufacturing method therefor | |
WO2003046102A1 (en) | Laminate structures for automotive trim components, and methods and tie layers | |
EP1134036A3 (en) | Method for treating coating film | |
CN207294676U (en) | Steel structure seam mending-leakage clad aluminum foil single-coated foam | |
JP2022530065A (en) | Self-adhesive prepreg | |
CN117465558A (en) | Polycarbonate solar automobile top cover and preparation method thereof | |
JPH04320827A (en) | Anticorrosive coating method of steel material | |
JP2017211004A (en) | Carbon fibers-bonded member, method for manufacturing the same, method for bonding carbon fiber members, method for manufacturing carbon fiber-reinforced member, method for manufacturing pressure container, and pressure container | |
JPH0519459B2 (en) | ||
JPS61255835A (en) | Method for corrosion-proof surface coating of metal material |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |