WO1997021750A1 - Polyurethane elastomers - Google Patents
Polyurethane elastomers Download PDFInfo
- Publication number
- WO1997021750A1 WO1997021750A1 PCT/EP1996/005035 EP9605035W WO9721750A1 WO 1997021750 A1 WO1997021750 A1 WO 1997021750A1 EP 9605035 W EP9605035 W EP 9605035W WO 9721750 A1 WO9721750 A1 WO 9721750A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- average
- polyol
- tan
- storage modulus
- Prior art date
Links
- 229920003225 polyurethane elastomer Polymers 0.000 title description 8
- 229920001971 elastomer Polymers 0.000 claims abstract description 22
- 239000000806 elastomer Substances 0.000 claims abstract description 22
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 21
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 21
- 238000003860 storage Methods 0.000 claims abstract description 16
- 229920005862 polyol Polymers 0.000 claims description 64
- 150000003077 polyols Chemical class 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000006353 oxyethylene group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004970 Chain extender Substances 0.000 claims description 9
- -1 poly(oxyethylene-oxypropylene) Polymers 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- SAMYCKUDTNLASP-UHFFFAOYSA-N hexane-2,2-diol Chemical compound CCCCC(C)(O)O SAMYCKUDTNLASP-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
-
- 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
- C08G18/48—Polyethers
-
- 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
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
-
- 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
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6552—Compounds of group C08G18/63
- C08G18/6558—Compounds of group C08G18/63 with compounds of group C08G18/32 or polyamines of C08G18/38
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
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- 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
- C08G2410/00—Soles
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- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/914—Polyurethane cellular product formed from a polyol which has been derived from at least two 1,2 epoxides as reactants
Definitions
- the present invention relates to novel polyurethane elastomers and a method for the preparation thereof.
- Polyurethane elastomers are made by reacting diisocyanates, such as toluene diisocyanate (TDI), 1,5 naphthalene diisocyanate (NDI) or 4,4' diphenylmethane diisocyanate (4, 4'-MDI), with high molecular weight polyols, such as polyester polyols or polyether polyols, and low molecular weight polyols or polyamines, such as ethylene glycol or butane diol.
- diisocyanates such as toluene diisocyanate (TDI), 1,5 naphthalene diisocyanate (NDI) or 4,4' diphenylmethane diisocyanate (4, 4'-MDI
- high molecular weight polyols such as polyester polyols or polyether polyols
- low molecular weight polyols or polyamines such as ethylene glycol or butane diol.
- High molecular weight polyether polyols mainly used are polytetrahydrofuran or polypropyleneoxide.
- Formulations comprising high amounts of 4, 4'-MDI and polyether polyols having high EO-contents have already been used to prepare flexible polyurethane foams, see for example EP-A-547764, EP-A-547765 and EP-A-549120. None of the known isocyanate-based elastomers however shows satisfactory dynamic modulus behaviour over a broad temperature range.
- the present invention relates to polyisocyanate-based elastomers having a ratio of the storage modulus (E') at 20°C and the storage modulus (E') at 120°C of between 0.75 and 1.5, a tan ⁇ at 100°C of less than 0.1 and a maximum value of the tan ⁇ of more than 0.8, the tan ⁇ being the ratio of the loss modulus (E'') and the storage modulus (E').
- the maximum value of the tan ⁇ is more than 1.0.
- the ratio of the storage modulus (E') at 20°C and the storage modulus (E') at 120°C is preferably between 0.8 and 1.2, and most preferably between 0.85 and 1 . 1 .
- tan ⁇ at 100°C is less than 0.05. Most preferably the tan ⁇ at 100°C is less than 0.03.
- the prime maximum of the tan ⁇ preferably occurs at a temperature below 0°C, most preferably below -10°C.
- the storage and loss modulus are measured by Dynamic Mechanical Thermal Analysis (DMTA measured according to ISO/DIS 6721-5).
- DMTA Dynamic Mechanical Thermal Analysis
- novel polyurethane elastomers can be made from formulations containing polyols having high oxyethylene contents or polyol blends containing polyester polyols and high concentrations of polyols having high oxyethylene contents, substantially pure 4,4'-MDI or a derivative thereof, and a low molecular weight chain extender and optionally a crosslinking agent.
- a method for the preparation of polyurethane elastomers from a reaction mixture comprising a polyisocyanate component, a polyol composition, a chain extender and optionally a crosslinking agent wherein the polyisocyanate component contains at least 85% by weight of 4,4'-diphenylmethane diisocyanate or a variant thereof, the polyol composition comprises at least one polyoxyalkylene polyol containing oxyethylene residues, said polyol composition having an average nominal hydroxyl functionality of from 2 to 4, an average hydroxyl equivalent weight of from 500 to 7000 and an average oxyethylene content of between 50 and 85% by weight, and the chain extender has an average hydroxyl equivalent weight of up to 250.
- the polyisocyanate component used in the invention may be any aromatic or aliphatic polyisocyanate such as TDI, NDI or pure 4,4'-diphenylmethane diisocyanate or mixtures of that diisocyanate with one or more other organic polyisocyanates, especially other diphenylmethane diisocyanate isomers, for example the 2,4'-isomer optionally in conjunction with the 2,2'-isomer.
- the polyisocyanate component may also be an MDI variant derived from a polyisocyanate composition containing at least 85% by weight of 4,4'-diphenyImethane diisocyanate.
- MDI variants are well known in the art and, for use in accordance with the invention, particularly include liquid products obtained by introducing uretonimine and/or carbodiimide groups into said polyisocyanate composition and/or by reacting with one or more polyols.
- Preferred as the polyisocyanate component are polyisocyanate compositions containing at least 90% by weight of 4,4'-diphenylmethane diisocyanate.
- Polyisocyanate compositions containing at least 95% by weight of 4,4'-diphenyImethane diisocyanate are most preferred.
- the polyol composition may consist of one or more polyether polyols optionally blended with other polyols, such as polyester polyols.
- the composition may comprise a single polyoxyalkylene polyol which preferably is a poly(oxyethylene-oxypropylene) polyol having the required functionality, equivalent weight and oxyethylene content.
- polyols are known in the art and may be obtained in conventional manner by reacting ethylene and propylene oxides simultaneously and/or sequentially in any order with an initiator such as water, a polyol, a hydroxyiamine, a polyamine and the like having from 2 to 4 active hydrogen atoms.
- the polyol composition may comprise a mixture of two or more polyoxyalkylene polyols such that the total composition has the required average functionality, equivalent weight and oxyethylene content.
- the polyoxyalkylene polyols present in such mixtures are preferably poly(oxyethylene-oxypropylene) polyols but one or more polyoxyethylene polyols and/or polyoxypropylene polyols may also be present.
- Preferred polyether polyol compositions comprise:
- a first polyol component comprising at least one polyoxyalkylene polyol containing oxyethylene residues, said polyol component having an average nominal hydroxyl functionality of from 2 to 4, an average hydroxyl equivalent weight of from 1000 to 5000 and an average oxyethylene content of from 60 to 85% by weight, and (b) from 25 to 0% by weight of another polyol component.
- Polyol component (b) suitably has an average functionality of from 2 to 4, an average equivalent weight of 1000 to 3000 and may be, for example, a polyoxypropylene polyol, a polyoxyethylene polyol or a poly (oxyethyleneoxypropylene) polyol containing less than 60% or more than 85% by weight of oxyethylene residues.
- average nominal hydroxyl functionality is used herein to indicate the average functionality (number of hydroxyl groups per molecule) of the polyol composition on the assumption that the average functionality of the polyoxyalkylene polyols present therein is identical with the average functionality (number of active hydrogen atoms per molecule) of the initiator(s) used in their preparation although in practice it will often be somewhat less because of some terminal unsaturation.
- the average nominal hydroxyl functionality of the polyol composition is from 2 to 3.
- the polyoxyalkylene polyol may contain dispersed polymer particles.
- Such polymer modified polyols have been fully described in the prior art and include products obtained by the in situ polymerisation of one or more vinyl monomers, for example acrylonitrile and styrene, in polyoxyalkylene polyols or by the in situ reaction between a polyisocyanate and an amino-or hydroxy-functional compound, for example triethanolamine, in the polyoxyalkylene.
- polyester polyols are also suitable as polyol (b) are polyester polyols.
- Polyester polyols which may be used include hydroxyl-terminated reaction products of polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,4-butanediol, bis (hydroxyethyl) terephthalate, glycerol, trimethylolpropane, hexanediol, neopentyl glycol, methylpentane diol, pentaerythritol or polyether polyols or mixtures of such polyhydric alcohols, and polycarboxylic acids, especially dicarboxylic acids or their ester-forming derivatives, for example succinic, glutaric and adipic acids or their dimethyl esters, sebacic acid, phthalic anhydride, tetrachlorophthalic anhydride or dimethyl terephthalate or mixtures thereof.
- polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, di
- Preferred polyesters have a number average molecular weight of 750-4000, especially 750-2500, and an average nominal functionality of 2-3.
- Suitable chain extenders include low molecular weight diols, aminoalcohols or diamines such as ethylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, propanediol, butanediol, pentanediol, hexanediol, 3- methylpentane-1,5-diol, ethanolamine or diethyltoluenediamine.
- Low molecular weight isocyanate-reactive compounds having an average functionality of 3 or more, such as glycerol, pentaerythritol or triethanolamine, may be added as crosslinking agents. It is preferred to add small amounts of water, most preferably less than 2% by weight based on the total weight of the isocyanate-reactive, to the formulation.
- the isocyanate-index of the reaction system taking account of the polyol composition, water and any other isocyanate-reactive species, for example chain extenders and opt. crosslinking agents, may be as low as 85 or as high as 120. Preferably, the isocyanate index is between 90 and 110. The most preferred isocyanate-index is between 95 and 105.
- the elastomer-forming reaction mixture may contain one or more of the additives conventional to such reaction mixtures.
- additives include catalysts, for example tertiary amines and tin compounds, surface-active agents and foam stabilisers, for example siloxane-oxyalkylene copolymers, flame retardants, organic and inorganic fillers, pigments, and internal mould release agents.
- the invention furthermore provides a reaction system comprising:
- polyol composition comprising at least one polyoxyalkylene polyol containing oxyethylene residues, said polyol composition having an average nominal hydroxyl functionality of from 2 to 4, an average hydroxyl equivalent weight of from 500 to 7000 and an average oxyethylene content of between 50 and 85% by weight;
- the known one-shot, semi-prepolymer or full prepolymer techniques may be applied together with mixing equipment conventionally used in the preparation of elastomers.
- the elastomers according to the invention are particularly suitable for use in applications where good energy-absorbing and fatigue properties are required and a good elastomeric behaviour over a broad temperature range, e.g. in the automotive and footwear industry.
- the invention is illustrated by the following examples in which all parts , percentages and ratios are by weight.
- Elastomers were bench mixed and moulded in a 15 ⁇ 10 ⁇ 1 cm mould in a conventional manner using the formulations given in Table I and the properties indicated in Table I were measured.
- the E' (20°C)/E(120°C) ratio of the elastomers according to the comparative examples is higher than 1.5 and their maximum value of the tan ⁇ is less than 0.8.
- Measurements were carried out according to ISO/DIS 6721-5 on a Rheometric Scientific DMTA apparatus using a 3-point bending method. Sample test dimensions were: length 1.0 cm, width 1.3 cm, thickness 0.4 cm. Applied strain amplitude 64 ⁇ 10 -4 cm, frequency 1 Hz, heating rate 2°C/min. The elastomer samples were pre-conditioned at 23°C/50% RH for 24 hours prior testing. The elastomer samples were quenched to -120°C (cooling rate 8.5°C/min) and held at that temperature for 5 minutes before heating of the sample was started.
- Figures 1-4 show the DMTA-curves of the examples 1-4.
- the DMTA-curves of the comparative examples 1 and 2 are shown in figures 5 and 6.
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002239482A CA2239482C (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomers |
DK96939064T DK0865458T4 (en) | 1995-12-08 | 1996-11-14 | polyurethane elastomers |
EP96939064A EP0865458B2 (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomers |
AT96939064T ATE198756T1 (en) | 1995-12-08 | 1996-11-14 | POLYURETHANE ELASTOMERS |
DE69611623T DE69611623T3 (en) | 1995-12-08 | 1996-11-14 | POLYURETHANE ELASTOMERS |
BR9611977A BR9611977A (en) | 1995-12-08 | 1996-11-14 | Elastomer based on polyisocyanate and process for the preparation of elastomers |
AU76258/96A AU718820B2 (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomers |
PL96327198A PL187124B1 (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomers |
ES96939064T ES2153601T5 (en) | 1995-12-08 | 1996-11-14 | ELASTOMEROS DE POLIURETANO. |
JP52164897A JP3892042B2 (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP95203405.6 | 1995-12-08 | ||
EP95203405 | 1995-12-08 |
Publications (1)
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WO1997021750A1 true WO1997021750A1 (en) | 1997-06-19 |
Family
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PCT/EP1996/005035 WO1997021750A1 (en) | 1995-12-08 | 1996-11-14 | Polyurethane elastomers |
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US (1) | US7307136B2 (en) |
EP (1) | EP0865458B2 (en) |
JP (2) | JP3892042B2 (en) |
KR (1) | KR100441926B1 (en) |
CN (1) | CN1210324C (en) |
AR (1) | AR005001A1 (en) |
AT (1) | ATE198756T1 (en) |
AU (1) | AU718820B2 (en) |
BR (1) | BR9611977A (en) |
CA (1) | CA2239482C (en) |
DE (1) | DE69611623T3 (en) |
DK (1) | DK0865458T4 (en) |
ES (1) | ES2153601T5 (en) |
ID (1) | ID19591A (en) |
MY (1) | MY129258A (en) |
PL (1) | PL187124B1 (en) |
PT (1) | PT865458E (en) |
TR (1) | TR199801042T2 (en) |
TW (1) | TW419489B (en) |
WO (1) | WO1997021750A1 (en) |
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WO2000055232A1 (en) * | 1999-03-17 | 2000-09-21 | Huntsman International Llc | Process for preparing moulded polyurethane material |
WO2002064656A2 (en) * | 2001-02-12 | 2002-08-22 | Noveon Ip Holdings Corp. | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
US6884824B2 (en) | 2000-07-14 | 2005-04-26 | Huntsman International Llc | Process for preparing an elastomer |
US7687548B2 (en) | 2002-07-01 | 2010-03-30 | Huntsman International Llc | Process for preparing a moulded polyurethane material |
EP2860208A1 (en) * | 2013-10-10 | 2015-04-15 | Yamaha Corporation | Urethane foam rubber and composition for forming urethane foam rubber |
WO2015156657A1 (en) * | 2013-04-09 | 2015-10-15 | Dow Química Mexicana S.A. De C.V. | Fast-curing adhesive composition |
US10823314B2 (en) | 2015-11-30 | 2020-11-03 | Junkosha Inc. | Polyurethane tube |
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DE10303172A1 (en) * | 2003-01-27 | 2004-07-29 | Basf Ag | Production of integral polyurethane foam for use in shoe soles and car manufacture involves reacting polyisocyanate with a special mixture of polyether-ol compounds plus chain extenders and other components |
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RU2613635C2 (en) | 2012-09-26 | 2017-03-21 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Polyurethane flexural stiffener |
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WO2017094699A1 (en) * | 2015-11-30 | 2017-06-08 | 株式会社 潤工社 | Polyurethane tube |
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WO2000055232A1 (en) * | 1999-03-17 | 2000-09-21 | Huntsman International Llc | Process for preparing moulded polyurethane material |
US6884824B2 (en) | 2000-07-14 | 2005-04-26 | Huntsman International Llc | Process for preparing an elastomer |
WO2002064656A2 (en) * | 2001-02-12 | 2002-08-22 | Noveon Ip Holdings Corp. | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
WO2002064656A3 (en) * | 2001-02-12 | 2002-10-24 | Noveon Ip Holdings Corp | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
US6734273B2 (en) | 2001-02-12 | 2004-05-11 | Noveon Ip Holdings Corp. | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
US7687548B2 (en) | 2002-07-01 | 2010-03-30 | Huntsman International Llc | Process for preparing a moulded polyurethane material |
WO2015156657A1 (en) * | 2013-04-09 | 2015-10-15 | Dow Química Mexicana S.A. De C.V. | Fast-curing adhesive composition |
EP2860208A1 (en) * | 2013-10-10 | 2015-04-15 | Yamaha Corporation | Urethane foam rubber and composition for forming urethane foam rubber |
US10823314B2 (en) | 2015-11-30 | 2020-11-03 | Junkosha Inc. | Polyurethane tube |
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