WO1999005194A1 - Beschichtungsmittel und verfahren zu dessen herstellung - Google Patents
Beschichtungsmittel und verfahren zu dessen herstellung Download PDFInfo
- Publication number
- WO1999005194A1 WO1999005194A1 PCT/EP1998/004438 EP9804438W WO9905194A1 WO 1999005194 A1 WO1999005194 A1 WO 1999005194A1 EP 9804438 W EP9804438 W EP 9804438W WO 9905194 A1 WO9905194 A1 WO 9905194A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- isocyanate
- ring structure
- coating composition
- groups
- Prior art date
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000012948 isocyanate Substances 0.000 claims abstract description 45
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 22
- 239000011230 binding agent Substances 0.000 claims abstract description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 19
- 239000013638 trimer Substances 0.000 claims abstract description 15
- 125000000524 functional group Chemical group 0.000 claims abstract description 11
- 125000006413 ring segment Chemical group 0.000 claims abstract description 11
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 7
- -1 Pinan Natural products 0.000 claims description 32
- 239000005056 polyisocyanate Substances 0.000 claims description 25
- 229920001228 polyisocyanate Polymers 0.000 claims description 25
- 239000008199 coating composition Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 229920000058 polyacrylate Polymers 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 229920003180 amino resin Polymers 0.000 claims description 3
- 150000001541 aziridines Chemical class 0.000 claims description 3
- BEWYHVAWEKZDPP-UHFFFAOYSA-N camphane Natural products C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- BWRHOYDPVJPXMF-UHFFFAOYSA-N cis-Caran Natural products C1C(C)CCC2C(C)(C)C12 BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003918 triazines Chemical class 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001743 benzylic group Chemical group 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000002298 terpene group Chemical group 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 41
- 239000002253 acid Substances 0.000 description 30
- 238000012360 testing method Methods 0.000 description 25
- 229920005862 polyol Polymers 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 16
- 239000000049 pigment Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000004922 lacquer Substances 0.000 description 14
- 230000009477 glass transition Effects 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- 239000004925 Acrylic resin Substances 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000004576 sand Substances 0.000 description 9
- 239000003973 paint Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 229920005749 polyurethane resin Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 238000006384 oligomerization reaction Methods 0.000 description 4
- 239000003791 organic solvent mixture Substances 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229920001567 vinyl ester resin Chemical class 0.000 description 4
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
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- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- 229930006742 bornane Natural products 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- SQHOHKQMTHROSF-UHFFFAOYSA-N but-1-en-2-ylbenzene Chemical compound CCC(=C)C1=CC=CC=C1 SQHOHKQMTHROSF-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
- 229930006741 carane Natural products 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical class [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- CQAZHDHHROTUHL-UHFFFAOYSA-N cyclohexane;methanol;prop-2-enoic acid Chemical compound OC.OC.OC(=O)C=C.C1CCCCC1 CQAZHDHHROTUHL-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical class CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical class CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical class CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical class CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- SKHDXTZKLIHWBC-UHFFFAOYSA-N n-(1-chlorohexan-2-ylidene)hydroxylamine Chemical compound CCCCC(CCl)=NO SKHDXTZKLIHWBC-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XVNKRRXASPPECQ-UHFFFAOYSA-N phenyl n-phenylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1 XVNKRRXASPPECQ-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003505 terpenes Chemical group 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Definitions
- the present invention relates to a two-component coating composition (2K system) which contains (I) at least one isocyanate as crosslinking agent and (II) at least one binder with functional groups which react with isocyanates, and the use thereof
- Two-component coating - or 2K systems for short - is a container made up of two different, separately manufactured and stored coating components, which are always traded in conjunction with one another and which are intended by a user who wants to produce a coating from a coating agent the production of the coating to be mixed with the coating agent.
- Such two-component systems are used, inter alia, for the production of top coats.
- the term top coats is understood here to mean lacquers which are used to produce the top lacquer layer.
- the top lacquer layer can be single-layer or multi-layer, in particular two-layer Two-coat top coats consist of a pigmented basecoat and an unpigmented clearcoat applied to the basecoat or only pigmented with transparent pigments.
- 2K systems which are mainly used for painting automobiles, usually consist of hydroxy-functional polyacrylates and / or polyesters and free isocyanate trimers of hexamethylene diisocyanate or isophorone diisocyanate (see, for example, the patents DE-4432260, DE-4432985)
- paints with good acid resistance have only a moderate scratch resistance.
- the acid resistance is insufficient
- the present invention is therefore based on the object of providing a two-component system which contains at least one isocyanate as crosslinking agent in its component (I) and at least one binder with functional groups which react with isocyanates in its component (II) and no longer has the disadvantages mentioned above, but in particular has good scratch resistance with good acid resistance at the same time
- Ia contains at least one isocyanate with at least one diisocyanate structural unit, which
- ii) has two isocyanate groups bonded to the ring structure, wherein iii) in the case of a non-aromatic ring structure
- At least one of the two isocyanate groups is or are connected to the ring structure via linear C2-C9-alkyl and / or linear C2-C] o-etheralkyl, which two radicals have no benzylic hydrogen atoms. and or
- Isocyanate units especially a trimer
- Ic) at least one partially blocked isocyanate Ia) and / or a partially blocked oligomer Ib), in particular a trimer Ib),
- the essential component of component (i) according to the invention is at least one isocyanate Ia) to be used according to the invention.
- This has at least one diisocyanate structural unit with a special structure
- the isocyanate Ia) to be used according to the invention can have two or more of these diisocyanate structural units, it has proven useful to use only one.
- the diisocyanate structural unit has the following features according to the invention:
- diisocyanate structural unit of the diisocyanate Ia) to be used according to the invention there are various possibilities for further training, which are described below
- the rings are hetero rings.
- the ring structure also contains different ring atoms, such as N atoms, O atoms or Si atoms.
- saturated hetero rings can be saturated or unsaturated act or aromatic hetero rings
- suitable saturated hetero rings are the silacyclopentane, silacyclohexane, oxolane, oxane, dioxane, morpholine, pyrrolidine, imidazolidine, pyrazolidine, piperidine or quinuclidine rings
- suitable unsaturated or aromatic hetero rings are pyrrole , Imidazole, pyrazole, pyridine, pyrimidine, pyrazine, pyridazine or triazine rings. It is preferred if the ring structure contains only carbon atoms as ring atoms
- the ring structure can be bridge-free on the one hand.
- the ring structure is a bicyclic terpene backbone, decalin, adamantane or quinuclidine
- bridges can be included.
- suitable terpene backbones are carane, norcarane, pinane, camphane or norbonane - basic frameworks
- the hydrogen atoms of a diisocyanate structural unit in particular the ring structure, can be substituted by groups or atoms which do not react either with isocyanates or with component (II) described below.
- suitable groups are nitro, alkyl, cycloalkyl, perfluoroalkyl, perfluorocycloalkyl - or aryl groups
- suitable atoms are halogen atoms, in particular fluorine
- the ring structure advantageously consists of 6 carbon atoms, in particular in the form of cyclohexane or benzene
- linear C 1 -C 4 -alkyl examples include methylene or ethylene and tri, tetra, penta-, hexa-, hepta-, octa- or nonamethylene residues, especially methylene residues
- the linear C 2 -Cjo ether alkyls are connected to the ring structure either via the oxygen atoms or via the alkanediyl radicals contained therein. They are preferably connected to them via the oxygen atoms.
- the indices 2 to 10 mean that 2 to 10 C atoms are contained in the ether alkyls
- the ether alkyls can only contain 1 oxygen atom. According to the invention, it is advantageous if 2 to 10, in particular 2 to 5, oxygen atoms are present in the chain. Then there are 1 or more, but in particular 2, C atoms between 2 oxygen atoms
- isocyanate Ia) to be used according to the invention is at least one
- both isocyanate groups can be bound via -CH2-, preferably to positions 1 and 3 of the ring system.
- the diisocyanate structural unit or the isocyanate Ia) to be used according to the invention then has, for example, the formula CgHg ⁇ C ⁇ -NCO ⁇
- one of the two isocyanate groups to be bonded directly to a ring atom of a non-aromatic ring system, in particular cyclohexane
- the second isocyanate group to be linked to a further ring atom, preferably in 1, via C -C 9 alkyl, in particular C3 alkyl , 2 configuration
- the diisocyanate structural unit or the isocyanate Ia) to be used according to the invention then has, for example, the formula C (5Hg (-N
- the isocyanate Ia) to be used according to the invention contains at least one diisocyanate structural unit with an unsaturated or aromatic ring system, in particular benzene, both isocyanate groups can be linked to this via C 2 -C -alkyl.
- the alkanediyl radicals contain no benzylic hydrogen atoms, but on in their place bear substituents R and R 2 which do not react either with isocyanates or with component (II).
- substituents R 1 and R 2 are C ] -C 10 alkyl, aryl or halogen, preferably -CH3
- the alkanediyl groups described above are preferably bonded to positions 1 and 3 of the benzene ring. However, binding to positions 1,2 and 1,4 is also possible in this case.
- the diisocyanate structural unit or the isocyanate Ia) to be used according to the invention then has, for example, the formula CgH4 (-C (CH3) 2-C2H4-NCO) 2
- the two isocyanate groups can, however, also be connected to the unsaturated or aromatic ring system, in particular benzene, via the C -C 0 ether alkyls described above. According to the invention, it is essential that the ether alkyls not carry any benzylic hydrogen atoms.
- one of the two isocyanate groups is bonded directly to a ring atom of an unsaturated or aromatic ring system, preferably a benzene ring, and that the second isocyanate group is bonded to another ring atom, for example via C3-Cg-alkyl, which has no benzylic hydrogen atoms , preferably in 1,2 configuration, the diisocanate structural unit or the isocyanate Ia) to be used according to the invention then has, for example, the formula CgH ⁇ -NCOX-
- At least one of the isocyanates Ia) to be used according to the invention described in detail above can be used as such as a crosslinking agent in component (I) according to the invention
- At least one oligomer Ib) can be used as the crosslinking agent in component (I) according to the invention.
- Oligomer Ib) is produced from isocyanate Ia), advantageously 2 to 10 monomer units being reacted and the trimerization Oligomerization and trimerization can be carried out with the aid of customary and known suitable catalysts 3 lead to the formation of uretdione, biuret, isocyanurate, urea and / or allophanate groups.
- oligomerization is also possible by reaction with low molecular weight polyols such as trimethylolpropane or homotrimethylolpropane, glycerin, neopentylglycol, dimethylolcyclohexane, ethylene glycol, diethylene glycol, methyl glycol, 2-propylene glycol, methyl glycol, propylene glycol -2-propylpropanediol-1,3, 2-ethyl-2-butylpropanediol-l, 3,2,2,4-trimethylpentanediol-1, 5 and 2,2,5-trimethylhexanediol-1,6, which, if necessary, are partially ethoxylated and / or propoxylated or otherwise hydrophilized
- At least one partially blocked isocyanate Ia) and / or at least one partially blocked oligomer Ib) can be used as crosslinking agent Ic) in component (I) according to the invention.
- suitable Blocking agents are the blocking agents known from US Pat. No.
- 4,444,954 such as i) phenols such as phenol, cresol, xylenol, nitrophenol, chlorophenol, ethylphenol, t-butylphenol, hydroxybenzoic acid, esters of this acid or 2,5-di-t-butyl-4- hydroxytoluene, ii) lactams, such as ⁇ -caprolactam, ⁇ -valerolactam, ⁇ -butyrolactam or ß-propiolactam, iii) active methylenic compounds, such as diethylmalonate, dimethylmalonate, ethyl acetoacetate, methyl acetoacetate or acetylacetone, iv) alcohols such as methanol, ethanol, n- Propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-amyl alcohol, t-amyl alcohol
- Methylolmelamine diacetone alcohol, ethylene chlorohydrin, ethylene bromohydrin, 1,3-dichloro-2-propanol or acetocyanhydrin
- mercaptans such as butyl mercaptan, hexyl mercaptan, t-butyl mercaptan, t-dodecyl mercaptan, 2-mercaptobenzothiazole, thiophenol, methylthiophenol or ethylthiophenol or methylthiophenol or ⁇ o acid amides such as acetoanilide, acetoanisidinamide, acrylamide, methacrylamide, acetic acid amide, stearic acid amide or benzamide, vii) imides such as succinimide, phthalimide or maleimide, viii) amines such as diphenylamine, phenylnaphthylamine, xylidine, n-
- oligomers Ib) or Ic) and trimers Ib) or Ic) to be used according to the invention described above advantageously have an NCO functionality of 2.0-5.0, preferably 2.2-4.0, in particular 2.5- 3.8
- the isocyanates Ia) to be used according to the invention described in detail above, their oligomers Ib) and / or trimers Ib) to be used according to the invention and / or the crosslinking agents Ic) to be used according to the invention can be the only crosslinking agents present in component (I) according to the invention
- crosslinking agents may also be present in component (I) according to the invention, preferably in a proportion by weight of 10-90%, in particular 40-60%, based on the total amount of crosslinking agents in component (I) U
- the above-mentioned isocyanates Ia) and / or their oligomers Ib) and / or trimers Ib), whose free isocyanate groups have been completely blocked with the conventional and known blocking agents described above, are particularly suitable as additional crosslinking agents
- customary and known isocyanates and / or their trimers and / or oligomers are suitable as additional crosslinking agents. These are any organic polyisocyanates with aliphatic, cycloaliphatic, araliphatic and / or aromatically bound isocyanate groups.
- Polyisocyanates with 2 to 5 isocyanate groups are preferred used per molecule and with viscosities of 100 to 2000 mPa s (at 23 ° C.)
- small amounts of organic solvent preferably 1 to 25% by weight, based on pure polyisocyanate, can be added to the polyisocyanates, in order to improve the incorporation of the isocyanate to improve and, if necessary, lower the viscosity of the polyisocyanate to a value within the abovementioned ranges.
- Solvents suitable as additives for the polyisocyanates are, for example, ethoxyethyl propionate, butyl acetate and the like
- Suitable isocyanates are, for example, in "Methods of Organic Chemistry", Houben-Weyl, Volume 14/2, 4th Edition, Georg Thieme Verlag, Stuttgart 1963, pages 61 to 70, W Siefken, Liebigs Ann Chem 562, 75 to 136, European patent EP-A-101 832 or US Pat. Nos. 3,290,350, UP-PS-4, 130,577 and US-PS-4,439,616. Some of them are also commercially available like 1,3-bis (2nd - Isocyanatoprop-2-yl) benzene from the American Cyanamid Company under the trade name TMXDI (META) R
- polyisocyanates examples include phenylene diisocyanate, tolylene diisocyanate, xylylidene diisocyanate, 1,3-bis (2-isocyanatoprop-2-yl) benzene ⁇ X (tetramethylxylylidene diisocyanate), bisphenylene diisocyanate,
- customary and known polyurethane prepolymers containing isocyanate groups which can be prepared by reacting the above-mentioned polyols with an excess of these polyisocyanates and which are preferably low-viscosity. It is also possible to use the customary and known isocyanurate groups, biuret groups, allophanate groups, urethane groups, urea groups and / or Polyisocyanates containing uretdione groups are used.
- Polyisocyanates containing urethane groups are obtained, for example, by reacting some of the isocyanate groups with the above-mentioned polyols , 4'-diisocyanate or dicyclohexylmethane-4,4'-diisocyanate or mixtures a Uses of these polyisocyanates Very particularly preferably, mixtures of uretdione, isocyanurate and / or allophanate groups containing polyisocyanates based on hexamethylene diisocyanate, such as those formed by catalytic oligomerization of hexamethylene diisocyanate using suitable catalysts, are used
- component (I) can be added as further crosslinkers
- component (II) The other essential constituent of the two-component system according to the invention is component (II). Its essential constituent, in turn, is binders based on polymers which contain functional groups which react with isocyanate groups
- polymers which are particularly suitable according to the invention are polyacrylates, polyesters, polyurethanes, acrylated polyurethanes or acrylated polyesters.
- a functional group which is particularly suitable according to the invention is the hydroxyl group.
- binders which are particularly suitable according to the invention are the abovementioned polymers with an OH number in the range 20 -400, especially in the 80-250 range, especially in the 80-200 range
- polyurethanes used as binders are known in principle.
- the polyurethane resins described in the literature for use in waterborne basecoats are suitable.
- highly suitable polyurethane resins are from European and German patents EP-A-355433, DE-OS m 3545618, DE-OS 3813866 are known or are described in the as yet unpublished German patent application DE 4005961 8.
- EP-A-355433 European and German patents EP-A-355433
- DE-OS m 3545618, DE-OS 3813866 are known or are described in the as yet unpublished German patent application DE 4005961 8.
- these polyurethane resins are dissolved in one or more organic solvents commitment
- the prepolymer containing isocyanate groups can be prepared by reacting polyols with a hydroxyl number of 10 to 1800, preferably 50 to 1200 mg KOH / g, with excess polyisocyanates at temperatures of up to 150 ° C., preferably 50 to 130 ° C., in organic solvents. which cannot react with isocyanates take place.
- the equivalent ratio of NCO to OH groups is between 2.0 1.0 and> 1.0 1.0, preferably between 1.4 1 and 1.1 1
- the polyols used to prepare the prepolymer can be low molecular weight and / or high molecular weight and they can contain inert anionic groups.
- low molecular weight polyols can be used. They have a molecular weight of 60 to about 400 and can be aliphatic, alicyclic or contain aromatic groups. Amounts of up to 30% by weight of the total polyol constituents are used. preferably about 2 to 20% by weight
- a high proportion of a predominantly linear polyol with a preferred OH number of 30 to 150 mg KOH / g is preferably added.
- polyester diols Up to 97% by weight of the total polyol can be obtained from saturated and unsaturated polyesters and / or polyethers with a molecular weight M n of 400 to 5000.
- the selected polyether diols should not introduce excessive amounts of ether groups, because otherwise the polymers formed swell in water.
- Polyester diols are produced by esterification of organic dicarboxylic acids or their anhydrides with organic diols or are derived from a hydroxy carboxylic acid or a lactone To produce branched polyester polyols, polyols or polycarboxylic acids with a higher valency can be used to a small extent
- Aliphatic, cycloaliphatic and / or aromatic polyisocyanates with at least two isocyanate groups per molecule are used as typical multifunctional isocyanates.
- the isomers or isomer mixtures of organic diisocyanates are preferred. Because of their good resistance to ultraviolet light, (cyclo) aliphatic diisocyanates give products with a low tendency to yellowing
- the polyisocyanate component used to form the prepolymer can also contain a proportion of high-quality polyisocyanates, provided that this does not cause gel formation.
- Triisocyanates have retained products which are obtained by trimerization or oligomerization of diisocyanates or by reaction of diisocyanates with polyfunctional OH or NH groups containing compounds are formed.
- the average functionality can optionally be reduced by adding monoisocyanates
- polyisocyanates examples include the polyisocyanates described as additional crosslinking agents in component (I) according to the invention and / or their oligomers or trimers in unblocked or partially blocked form
- carrier groups Compounds which contain two H-active groups which react with isocyanate groups and at least one group which ensures water dispersibility (carrier groups) can be used to produce water-compatible polyurethanes.
- Suitable carrier groups are nonionic groups (e.g. polyether), anionic groups, mixtures of these two groups or cationic groups
- Such a large number of acids can be incorporated into the polyurethane resin that the neutralized product can be stably dispersed in water.
- This is done by compounds which contain two H-active groups which react with isocyanate groups and at least one group capable of forming anions.
- Suitable groups which react with isocyanate groups are especially hydroxyl groups and primary and / or secondary amino groups.
- Groups that are capable of forming anions are carboxyl, sulfonic acid and / or phosphonic acid groups. Carboxylic acid or carboxylate groups are preferably used.
- the isocyanate groups of the diisocyanate are preferably compared to the others Reacting isocyanate group-reactive groups of the molecule
- alkanoic acids with two substituents on the ⁇ -position carbon atom are used.
- the substituent can be a hydroxyl group, an alkyl group or an alkylol group.
- These polyols have at least one, in a Generally 1 to 3 carboxyl groups in the molecule. They have two to about 25, preferably 3 to 10 carbon atoms.
- the polyol containing carboxyl groups can make up 3 to 100% by weight, preferably 5 to 50% by weight, of the total polyol component in the NCO prepolymer
- the amount of ionizable carboxyl groups available in salt form is generally at least 0.4% by weight, preferably at least 0.7% by weight, based on the solid.
- the upper limit is about 6% by weight.
- the amount of dihydroxy acidic acids in the unneutralized prepolymer gives an acid number of at least 5, preferably at least 10 In the case of very low acid numbers, further measures are generally necessary to achieve water dispersibility.
- the upper limit of the acid number is 70, preferably 40 mg KOH / g, based on the solid
- Advantageous NCO prepolymers can be prepared by simultaneously reacting the polyol or polyol mixture with an excess of diisocyanate. On the other hand, the reaction can also be carried out stepwise in a prescribed order. Examples are described in German patents DE-OS 26 24 442 and DE-OS 32 10 051 The reaction temperature is up to 150 ° C, with a temperature in the range of 50 to 130 ° C being preferred
- Advantageous NCO prepolymers contain at least about 0.5% by weight of isocyanate groups, preferably at least 1% by weight of NCO, based on solids.
- the upper limit is about 15% by weight, preferably 10% by weight, particularly preferably 5% by weight.
- the reaction can optionally be carried out in the presence of a catalyst, such as organotin compounds and / or tertiary amines.
- a catalyst such as organotin compounds and / or tertiary amines.
- the amount of solvent can vary within wide limits and should be sufficient to form a prepolymer solution with a suitable viscosity. In general, 10 to 70% by weight of solvent, preferably 20 to 50% by weight -% solvent, based on the solids used
- the isocyanate groups still present in the prepolymer are reacted with a modifier. This reaction leads in particular to further linking and increasing the molecular weight.
- the amount of this modifier is determined by its functionality and the NCO content of the prepolymer.
- the equivalent ratio of the active hydrogen atoms in the modifier to the NCO- Groups in the prepolymer should generally be less than 3 1 and preferably in the range between 1 1 and 2 1
- Preferred modifiers for the reaction with the prepolymer are di-, particularly preferably tri- and / or polyols
- modifiers for example polyamines
- the reaction of the prepolymer with the modifier can be carried out (controllable) in an organic solvent and that no undesired reactions, such as e.g. B the gelation frequently observed when using polyamines occurs at the dropping point of the amine
- Trimethylolpropane Trimethylolpropane, glycerol, erythritol, mesoerythritol, arabitol, adonite, etc. are mentioned as examples of polyols containing at least three hydroxyl groups. Trimethylolpropane is preferably used.
- the reaction of the prepolymer with the tri- and / or polyols is preferably controlled by the stochiometry of the compounds used so that there are chain extensions '3
- polyacrylate resins used as binders are also known and are described, for example, in DE-OS 3832826.
- Water-thinnable or water-dispersible polyacrylate resins are generally suitable. They can advantageously be prepared in the form of organic solutions
- Polyacrylate resins are preferably used for clearcoats
- Hydroxyl numbers from 40 to 240 preferably 60 to 210, very particularly preferably 100 to 200, acid numbers from 0 to 35, preferably 0 to 23, very particularly preferably 3.9 to 15.5, glass transition temperatures from -35 to +70
- 0C preferably -20 to +40 ° C, very particularly preferably -10 to + 15 ° C, and number average molecular weights M "from 1500 to 30,000, preferably 2000 to 15000, very particularly preferably 2500 to 5000, the ratio M w / M n is between 1.2 and 5.0, preferably 1, 2 and 4.0
- the glass transition temperature of the polyacrylate resins is determined by the type and amount of the monomers used and can be estimated in a customary and known manner from the number of n different monomers polymerized in the polyacrylate resin, the weight fraction of the nth monomer and the glass transition temperature of the homopolymer from the nth monomer
- the selection of the monomers can therefore be carried out in a simple manner by the person skilled in the art
- Measures for controlling the molecular weight e.g. selection of appropriate polymerization initiators, use of
- the hydroxy-functional binder component used is, for example, polyacrylate resins which can be prepared by (al) 10 to 92, preferably 20 to 60% by weight of an alkyl or cycloalkylacrylate or an alkyl or cycloalkylmethacrylate having 1 to 18, preferably 4 to 13, carbon atoms in the alkyl - or cycloalkyl radical or mixtures of such monomers, (b1) 8 to 60, preferably 12.5 to 38.5% by weight of a hydroxyalkyl (meth) acrylate and / or a hydroxycycloalkyl (meth) acrylate with 2 to 4 carbon atoms in the hydroxyalkyl radical or Mixtures of such monomers, (cl) 0.0 to 5.0, preferably 0.7 to 3.0% by weight of acrylic acid or methacrylic acid or mixtures of these monomers and (dl) 0 to 50, preferably 0
- Examples of (bl) components are hydroxyethyl, hydroxypropyl hydroxybutyl or cyclohexane dimethanol acrylate or methacrylate and adduct and (meth) acrylic acid
- Examples of (dl) components are vinylaromatics, such as styrene, vinyltoluene, methylstyrene, ⁇ -ethylstyrene, nucleus-substituted diethylstyrenes, Isopropyl styrene, butyl styrenes and methoxystyrenes, vinyl ethers, such as, for example, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether and isobutyl vinyl ether and vinyl esters, such as, for example, vinyl acetate, Vinyl propionate, vinyl butyrate, vinyl pivalate and the vinyl ester of 2-methyl
- Polyhydroxy resins which are obtainable by (AI) 10 to 51% by weight, preferably 25 to 41% by weight, 4-hydroxy-n-butyl acrylate or 4-hydroxy-n-butyl methacrylate or a are also used, for example, as the hydroxy-functional binder component Mixture of 4-hydroxy-n-butyl acrylate and 4-hydroxy-n-butyl methacrylate, preferably 4-hydroxy-n-butyl acrylate, (A2) 0 to 36% by weight o, preferably 0.1 to 20% by weight, one of (AI) various hydroxyl-containing esters of acrylic acid or a hydroxyl-containing ester of methacrylic acid or a mixture of such monomers, (A3) 28 to 85% by weight, preferably 40 to 70% by weight> one of (AI) and (A2) different aliphatic or cycloaliphatic ester of methacrylic acid with at least 4 carbon atoms in the alcohol residue or a mixture of such monomers, (A4) 0 to 3% by weight
- component (A3) are aliphatic esters of methacrylic acid with 4 to 20 carbon atoms in the alcohol radical, such as, for example, n-butyl, isobutyl, tert-Butyl, 2-ethylhexyl, stearyl and lauryl methacrylate, and cycloaliphatic esters of methacrylic acid such as, for example, cyclohexyl methacrylate.
- component (A4) preference is given to using acrylic acid and / or methacrylic acid.
- component (A5) examples are vinylaromatic hydrocarbons , for example styrene, ⁇ -alkylstyrene and vinyltuluol, amides of acrylic acid and methacrylic acid, for example methacrylamide and acrylic lamide, nitriles of acrylic acid and methacrylic acid, vinyl ether and vinyl ester
- component (A5) preferably vinyl aromatic hydrocarbons, in particular styrene, are used.
- the composition of component (A5) should preferably be such that when component (A5) is polymerized alone, a polymer with a glass transition temperature of +70 to +120 degrees C, preferably from +80 to +100 degrees C.
- the acid number can be set by the person skilled in the art by using appropriate amounts of component (A4). The same applies analogously to the setting of the hydroxyl number Quantity of component (AI) and (A2) controllable
- component (AI) is used with 21-62, preferably 41-57% by weight component (A3) is used with 28-75, preferably 34-54% by weight % used
- Component (A3) is chosen with regard to its composition so that when component (A3) is polymerized alone, a polymethacrylate resin with a glass transition temperature 2 2 »ture from +10 to +100 degrees C, preferably from +20 to +60 degrees C, is obtained.
- component (A2) examples are: hydroxyalkyl esters of acrylic acid, such as, for example, hydroxyethyl acrylate and hydroxypropyl acrylate, and hydroxyalkyl esters of methacrylic acid, such as, for example, hydroxyethyl methacrylate and hydroxypropyl methacrylate, the choice being such that component (A2) is polymerized alone Polyacrylate resin with a glass transition temperature of 0 to +80 degrees C, preferably from +20 to +60 degrees C is obtained.
- component (A3) examples are aliphatic esters of methacrylic acid with 4 to 20 carbon atoms in the alcohol radical, such as, for example, n-butyl, isobutyl, tert-butyl, 2-ethylhexyl, stearyl and Lauryl methacrylate, and cycloaliphatic esters of methacrylic acid such as, for example, cyclohexyl methacrylate.
- Acrylic acid and / or methacrylic acid are preferably used as component (A4).
- component (A5) vinylaromatic hydrocarbons, for example styrene, ⁇ -alkylstyrene and vinyltuluol, amides of acrylic acid and methacrylic acid, for example methacrylamide and acrylamide, nitriles of acrylic acid and methacrylic acid, vinyl ethers and vinyl esters.
- Vinylaromatic hydrocarbons, in particular styrene are preferably used as component (A5).
- the composition of component (A5) should preferably be such that when component (A5) is polymerized alone, a polymer with a glass transition temperature of +70 to +120 degrees C. , preferably from +80 to + 100 degrees C.
- the acid number can be set by a person skilled in the art by using appropriate amounts of component (A4). The same applies to the setting of the hydroxyl number. It can be controlled via the amount of component (AI) and (A2) used.
- Component (AI) is used with 21-62, preferably 41-57% by weight.
- Component (A3) is used with 28-75, preferably 34-54 wt .-%.
- the component (A3) will Q chosen with regard to the composition so that when component (A3) is polymerized alone, a polymer with a glass transition temperature of 0 to
- Component (A5) is selected with regard to its composition such that when component (A5) is polymerized alone, a polymer with a glass transition temperature of +70 to +120 ° C. is obtained
- the hydroxyl number of the polyacrylate resin obtained is in the range 100-240, preferably in the range 160-220, most preferably in the range 170-200. It is preferred if the acrylate resin has many primary hydroxyl groups (for example 50-100%) of the OH groups in total) It is further preferred if the acrylic resin has a glass transition temperature of at most 70 ° C. preferably -40 to +30 ° C, finally it is preferred if the polyacrylate resin is selected so that the hardened coating agent in the rubber-elastic range
- Memory module E ' more than 10 ⁇ 5 Pa, preferably more than 10' - 'Pa, and one
- polyacrylate resins can be prepared by generally well-known polymerization processes (see, for example, Houben-Weyl, Methods of Organic Chemistry, 4th edition, volume 14/1, pages 24 to 255 (1961)) preferably produced with the aid of solvent polymerization.
- An organic solvent or solvent mixture is usually introduced and heated to boiling.
- the monomer mixture to be polymerized and one or more polymerization initiators are then continuously added to this organic solvent or solvent mixture.
- the polymerization is carried out at temperatures between 100 and 180 ° C, preferably between 130 and 150 ° C. Free radical initiators are preferably used as the polymerization initiators.
- initiators are usually chosen so that the supply of radicals is as constant as possible during the feed phase
- initiators that can be used include dialkyl peroxides such as di-tert-butyl peroxide and dicumyl peroxide, hydroperoxides such as cumene hydroperoxide and tert-butyl hydroperoxide, peresters such as tert-butyl perbenzoate, tert-butyl perpivalate, tert-butyl per-3,5,5-trimethylhexanoate and tert - Butylper-2-ethylhexanoate or azo compounds such as azobisisobutyronitrile
- the polymerization conditions (reaction temperature, feed time of the monomer mixture, amount and type of organic solvents and polymerization initiators, possibly also the use of molecular weight regulators, for example mercaptans, thioglycolic acid esters and Hydrogen chloride) are selected so that the polyacrylate resins
- Water-thinnable or water-dispersible polyester resins which can be prepared in the form of organic solutions can also be used as binders.
- binders For example, corresponding commercially available water-thinnable or water-dispersible polyester resins and the polyester resins normally used in water-based paints are used
- the hydroxy-functional binder component used in particular for clearcoats for example, polyester resins or alkyd resins, which can be prepared by (a) a cycloaliphatic or aliphatic polycarboxylic acid or a mixture of such polycarboxylic acids or their anhydrides (b) an aliphatic or cycloaliphatic polyol with more than two hydroxyl groups in the molecule or a mixture of such polyols (c) an aliphatic or cycloaliphatic diol or a mixture of such diols and (d) an aliphatic linear or branched saturated monocarboxylic acid or a mixture of such monocarboxylic acids in
- component (b2) Camphoric anhydride, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimeline acid, cork acid, azelaic acid and sebacic acid.
- component (b2) are pentaerythritol, trimethylolpropane, trimethylol han and glycolic glycol , Propylene glycol, neopentyl glycol, 2-methyl-2-propylpropanediol-1, 3,2-ethyl-2-butylpropanediol-1,3, 2,2,4-trimethylpentanediol-1,5, 2,2,5-trimethylhexanediol - 1,6, hydroxypivalic acid neopentylglycol ester and dimethylolcyclohexane
- component (d2) include 2-ethylhexanoic acid, lauric acid, isooctanoic acid, isononanoic
- component (II) can additionally contain other water-thinnable or water-dispersible binders
- Component (II) may also contain crosslinking agents which only react with the reactive functional groups of the binders at relatively high temperatures.
- suitable crosslinking agents are the completely blocked isocyanates to be used according to the invention and / or customary and known polyisocyanates described in component (I) , the tris (alkoxyarbonylamino) triazines and / or the customary and known melamine resins, aminoplast resins, carbodiimides, aziridines, epoxides and / or siloxanes
- the 2K system according to the invention can contain UV absorbers, preferably triazine or benzotriazole compounds and radical scavengers in at least one of the two components (I) and / or (II).
- the 2K system according to the invention can also contain rheological agents, catalysts such as organotin compounds or containing bismuth compounds and other paint auxiliaries in at least one of the two components (I) and / or (II).
- pigments of any kind for example color pigments such as azo pigments, phthalocyanine pigments, carbonyl pigments, dioxazine pigments, titanium dioxide, carbon black, iron oxides and chromium or cobalt oxides, can also be present , or effect pigments such as metal plate pigments, in particular Aluminum plate pigments and pearlescent pigments, to be incorporated in at least one of the two components (I) and / or (II).
- no or transparent pigments are provided
- composition of the 2K system according to the invention contains the components (I) and (II) essential to the invention in broadly varying weight ratios which essentially depend on the concentrations of the reactive functional components present in components (I) and (II) Groups and according to the application conditions for the 2K system.
- the person skilled in the art can therefore determine the weight ratios required for a special application in a simple manner
- the amounts of components (I) and (II) in the ratios to one another are chosen such that the ratio “functional groups which react with isocyanate groups NCO”, in particular “OH groups NCO”, 1.0 0.5 to 1.0 2.0, preferably 1.0 0.8 to 1.0 1.5, in particular 1.0 0.8 to 1.0 1.3
- the two components (I) and (II) are produced using the customary methods from the individual constituents with stirring.
- the two-component system according to the invention is produced from components (I) and (II) likewise by stirring or using the dispersion Devices usually used, for example by means of a dissolver or the like or by means of 2-component metering and mixing systems which are also usually used, or by means of the device described in German Patent DE-A-195 10 651, page 2, line 62, to page 4, line 5, Process described for the preparation of aqueous 2-component polyurethane coatings ⁇ 5
- the components, in particular component (II) can be formulated as non-aqueous (ie with organic solvents) or as aqueous components.
- components (I) and (II) can also be formulated to be largely anhydrous and largely free of organic solvents, but as being dispersible in water Aqueous coating compositions obtained by mixing the components and adding water.
- a water-dispersible or soluble component (II) can be formulated in a customary manner, for example by introducing acidic groups into the binder, which are then mixed with a customary base, for example ammonia or an orga African amine such as triethylamine can be neutralized.
- the solution or dispersion of a water-dispersible component (I) and / or (II) in water is carried out in the usual manner, for example by vigorous stirring, if necessary with gentle heating.
- a solution or dispersion in water using nonionic emulsifiers In this respect, reference is also made to standard processes for the production of aqueous paints
- the invention also relates to the use of the 2K system according to the invention for coating a substrate.
- Component (I) and component (II) are mixed together, applied and baked together before the application, preferably immediately before the application, to form the coating composition
- Component (I) and component (II) can optionally be applied using a special two-component application device and baked together
- Primed or non-primed plastic parts and plastic films such as ABS, AMMA, ASA, CA, CAB, EP, UF, CF, MF, MPF, PF, PAN, PA, PC can be used with the aqueous lacquers produced using the two-component system according to the invention , PE, HDPE, LDPE, LLDPE, UFTMWPE, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (short names painted according to DIN 7728T1)
- the plastic parts and films to be coated can of course also consist of polymer blends, modified plastics or fiber-reinforced plastics.
- the coating compositions according to the invention are preferred for coating PPE / PA blends, polycarbonate blends (e.g. PC / AS A, PC / PBT) and polypropylene -Blends used
- the coating compositions according to the invention are used for the plastics typically used in vehicle construction, in particular motor vehicle construction
- non-functionalized and / or non-polar substrate surfaces these must be subjected to a pretreatment, such as plasma or flame treatment, before coating
- the two-component system according to the invention is used for the production of single- or multi-layer lacquers and preferably for the production of top coats.
- it can also be used for the production of a clear lacquer to be applied over a basecoat film, for example a clear lacquer of a multi-layer lacquer produced by the wet-on-wet method his
- the plastics or the other substrates can also be coated directly with the clear coat or top coat
- the coating compositions can also be applied to other substrates, such as metal, wood, glass or paper.
- the application is carried out using customary methods, for example spraying, knife coating, dipping or brushing
- the two-component systems according to the invention are usually cured at temperatures from room temperature of up to 250 ° C., preferably at temperatures between 60 and 180 ° C. and particularly preferably at temperatures between 60 and 150 ° C. Higher curing temperatures can also be used in special application forms
- the 2-component systems according to the invention are preferably used for the production of top coats.
- the 2-component systems according to the invention can be used both for the serial and also for the refinishing of automobile bodies
- composition B An inventive (composition B) and a conventional 2-component system (composition A) were produced from the components listed in Table 1 and applied to test panels.
- composition A Composition B
- a) dissolution of a polyisocyanate based on hexamethylene diisocyanate (80% dissolution of Desmodur N 3390 from Bayer AG in butyl acetate / solvent naphtha)
- b) dissolving of the polyisocyanate Ia) to be used according to the invention, isocyanate of 1,3-bis- (methylene isocyanate) -cyclohexane with an NCO-
- Methoxypropylacetate / Solventnaphtha c) usual and known acrylate resin from styrene, n-butyl methacrylate, t-butyl acrylate, hydroxypropyl methacrylate and acrylic acid, as described in DE 197 25 188.9, diluted to 53% solids content with a
- the varnish surface was damaged with a sieve fabric that was loaded with a mass.
- the sieve fabric and the varnish surface were liberally wetted with a detergent solution.
- the test panel was pushed back and forth under the sieve fabric by means of a motor drive
- test panels To produce the test panels, first an electro-dip lacquer with a layer thickness of 18 - 22 ⁇ m, then a filler with a layer thickness of 35 - 40 ⁇ m, then a black basecoat with a layer thickness of 20 - 25 ⁇ m and finally the coating agent to be tested with a layer thickness 40 - 45 ⁇ m applied and harded in each case. After the lacquers had been applied, the panels were stored at room temperature for 2 weeks before the test was carried out
- the test specimen was an eraser (4.5 ⁇ 2.0 cm, wide side perpendicular to the direction of scratching) covered with nylon mesh (No. 11.3 ⁇ m mesh, Tg 50 ° C.).
- the coating weight was 2000 g
- the scratch resistance was determined after the sand test.
- the lacquer surface was loaded with sand (20 g quartz-silver sand 1.5-2.0 mm).
- the sand was placed in a beaker (floor cut off flat), which was firmly attached to the test board
- the same test boards were used as described in the burst test above.
- the table with the cup and the sand was shaken by means of a motor drive.
- the movement of the loose sand caused damage to the paint surface (100 double strokes in 20 s) Abrasion cleaned, carefully wiped under a cold water jet and then dried with compressed air.
- the gloss was measured according to DIN 67530 before and after damage
- the BART BASF ACID RESISTANCE TEST
- the coating on a gradient oven was exposed to further temperature loads after baking (30 min 40 ° C, 50 ° C, 60 ° C and 70 ° C)
- Each individual marking (spot) was evaluated and the result for each coating was recorded in a suitable form (e.g. grade sums for a temperature)
- Table 3 The acid resistance of the coatings produced from the (B) and the conventional (A) two-component systems according to the invention
- composition A Composition B
- Demineralized water 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
- Demineralized water 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE59805833T DE59805833D1 (de) | 1997-07-22 | 1998-07-16 | Beschichtungsmittel und verfahren zu dessen herstellung |
US09/463,054 US6630537B1 (en) | 1997-07-22 | 1998-07-16 | Coating agent and method for producing same |
EP98940238A EP0998508B1 (de) | 1997-07-22 | 1998-07-16 | Beschichtungsmittel und verfahren zu dessen herstellung |
AU88622/98A AU8862298A (en) | 1997-07-22 | 1998-07-16 | Coating agent and method for producing same |
BR9811522-7A BR9811522A (pt) | 1997-07-22 | 1998-07-16 | Agente de revestimento e processos para a sua preparação |
JP2000504182A JP2001510868A (ja) | 1997-07-22 | 1998-07-16 | 塗料及びその製法 |
PL98338431A PL338431A1 (en) | 1997-07-22 | 1998-07-16 | Coating material and method of obtaining same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19731384.1 | 1997-07-22 | ||
DE19731384 | 1997-07-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999005194A1 true WO1999005194A1 (de) | 1999-02-04 |
Family
ID=7836475
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/004438 WO1999005194A1 (de) | 1997-07-22 | 1998-07-16 | Beschichtungsmittel und verfahren zu dessen herstellung |
Country Status (11)
Country | Link |
---|---|
US (1) | US6630537B1 (de) |
EP (1) | EP0998508B1 (de) |
JP (1) | JP2001510868A (de) |
AU (1) | AU8862298A (de) |
BR (1) | BR9811522A (de) |
DE (1) | DE59805833D1 (de) |
ES (1) | ES2185202T3 (de) |
MX (1) | MX215723B (de) |
PL (1) | PL338431A1 (de) |
WO (1) | WO1999005194A1 (de) |
ZA (1) | ZA986520B (de) |
Cited By (3)
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---|---|---|---|---|
US6649706B1 (en) | 1999-05-25 | 2003-11-18 | Basf Coatings Ag | Thixotroping agent |
US6652916B1 (en) | 1999-05-25 | 2003-11-25 | Basf Coatings Ag | Coating material comprising a mixture that consists of at least one wetting agent and of ureas and/or urea derivatives serving as thixotropic agents |
US7019042B2 (en) | 2000-08-26 | 2006-03-28 | Basf Coatings Ag | Thixotropic agent that can be activated using actinic radiation, a method for its production and the use thereof |
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EP1193279A3 (de) * | 2000-09-28 | 2002-05-08 | Kansai Paint Co. Ltd. | Grundierbeschichtungszusammensetzung und Reparaturbeschichtungsverfahren |
DE10126647A1 (de) * | 2001-06-01 | 2002-12-12 | Basf Coatings Ag | Rheologiehilfsmittel, Verfahren zu seiner Herstellung und seine Verwendung |
DE10139262C1 (de) * | 2001-08-09 | 2003-01-02 | Basf Coatings Ag | Rheologiehilfsmittel, Verfahren zu seiner Herstellung und seine Verwendung |
DE10140156A1 (de) * | 2001-08-16 | 2003-03-20 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbare Beschichtungsstoffe und ihre Verwendung |
US8686090B2 (en) * | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
US7682665B2 (en) * | 2004-12-15 | 2010-03-23 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing novel aspartic amine compounds |
US7674499B2 (en) * | 2004-12-15 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing novel aspartic amine compounds |
US7608303B2 (en) * | 2004-12-15 | 2009-10-27 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing aspartic amine compounds |
US20110021694A1 (en) * | 2009-07-23 | 2011-01-27 | E.I. Du Pont De Nemours And Company | Polyesterurethane for coating compositions |
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- 1998-07-16 AU AU88622/98A patent/AU8862298A/en not_active Abandoned
- 1998-07-16 WO PCT/EP1998/004438 patent/WO1999005194A1/de active IP Right Grant
- 1998-07-16 EP EP98940238A patent/EP0998508B1/de not_active Expired - Lifetime
- 1998-07-16 JP JP2000504182A patent/JP2001510868A/ja active Pending
- 1998-07-16 ES ES98940238T patent/ES2185202T3/es not_active Expired - Lifetime
- 1998-07-16 BR BR9811522-7A patent/BR9811522A/pt active Search and Examination
- 1998-07-16 US US09/463,054 patent/US6630537B1/en not_active Expired - Fee Related
- 1998-07-16 PL PL98338431A patent/PL338431A1/xx unknown
- 1998-07-22 ZA ZA986520A patent/ZA986520B/xx unknown
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2000
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6649706B1 (en) | 1999-05-25 | 2003-11-18 | Basf Coatings Ag | Thixotroping agent |
US6652916B1 (en) | 1999-05-25 | 2003-11-25 | Basf Coatings Ag | Coating material comprising a mixture that consists of at least one wetting agent and of ureas and/or urea derivatives serving as thixotropic agents |
US7019042B2 (en) | 2000-08-26 | 2006-03-28 | Basf Coatings Ag | Thixotropic agent that can be activated using actinic radiation, a method for its production and the use thereof |
Also Published As
Publication number | Publication date |
---|---|
PL338431A1 (en) | 2000-11-06 |
AU8862298A (en) | 1999-02-16 |
BR9811522A (pt) | 2000-08-22 |
US6630537B1 (en) | 2003-10-07 |
ZA986520B (en) | 1999-03-18 |
MXPA00000666A (es) | 2001-07-01 |
ES2185202T3 (es) | 2003-04-16 |
EP0998508B1 (de) | 2002-10-02 |
DE59805833D1 (de) | 2002-11-07 |
JP2001510868A (ja) | 2001-08-07 |
MX215723B (es) | 2003-08-08 |
EP0998508A1 (de) | 2000-05-10 |
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