DE60001154T2 - Hochtemperaturbeständige polyurethanpolymere - Google Patents
Hochtemperaturbeständige polyurethanpolymereInfo
- Publication number
- DE60001154T2 DE60001154T2 DE60001154T DE60001154T DE60001154T2 DE 60001154 T2 DE60001154 T2 DE 60001154T2 DE 60001154 T DE60001154 T DE 60001154T DE 60001154 T DE60001154 T DE 60001154T DE 60001154 T2 DE60001154 T2 DE 60001154T2
- Authority
- DE
- Germany
- Prior art keywords
- polyurethane
- butylene oxide
- present
- composition
- polyisocyanate prepolymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 59
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 59
- 229920000642 polymer Polymers 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 48
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 229920005862 polyol Polymers 0.000 claims description 43
- 150000003077 polyols Chemical class 0.000 claims description 42
- 229920000768 polyamine Polymers 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 239000000806 elastomer Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000010107 reaction injection moulding Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 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 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- -1 poly(oxybutyleneoxyethylene) Polymers 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920002396 Polyurea Polymers 0.000 description 6
- 230000007547 defect Effects 0.000 description 6
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 208000002352 blister Diseases 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- 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 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- OMXAWIAIGXKAQA-UHFFFAOYSA-N 1-(2-tert-butylphenyl)-2,2-dimethylpropane-1,1-diamine Chemical compound CC(C)(C)C1=CC=CC=C1C(N)(N)C(C)(C)C OMXAWIAIGXKAQA-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000004000 hexols Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- C08G18/48—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
- C08G18/70—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
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene 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
- C08G18/28—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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Artificial Filaments (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12150299P | 1999-02-23 | 1999-02-23 | |
| PCT/US2000/004550 WO2000050484A1 (en) | 1999-02-23 | 2000-02-23 | High temperature resistant polyurethane polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60001154D1 DE60001154D1 (en) | 2003-02-13 |
| DE60001154T2 true DE60001154T2 (de) | 2003-07-17 |
Family
ID=22397124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60001154T Expired - Lifetime DE60001154T2 (de) | 1999-02-23 | 2000-02-23 | Hochtemperaturbeständige polyurethanpolymere |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6613864B1 (enExample) |
| EP (1) | EP1161472B1 (enExample) |
| JP (1) | JP2002537455A (enExample) |
| KR (1) | KR100602805B1 (enExample) |
| CN (1) | CN1152071C (enExample) |
| AT (1) | ATE230769T1 (enExample) |
| AU (1) | AU3240600A (enExample) |
| CA (1) | CA2362141C (enExample) |
| DE (1) | DE60001154T2 (enExample) |
| ES (1) | ES2190404T3 (enExample) |
| WO (1) | WO2000050484A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6287442B1 (en) * | 2000-05-24 | 2001-09-11 | Patent Holding Company | Injection molded thermoplastic integrated front end reinforcement and method of making same |
| DE10038941C2 (de) * | 2000-08-09 | 2002-08-14 | Skw Bauwerkstoffe Deutschland | Polyurethan-(Polymer-Hybrid-)Dispersion mit verringerter Hydrophilie, Verfahren zu ihrer Herstellung sowie deren Verwendung |
| MXPA03011419A (es) * | 2001-06-15 | 2004-06-30 | Huntsman Spec Chem Corp | Extensores sinergicos de cadena de amina en elastomeros de rocio de poliurea. |
| DE10160375B4 (de) * | 2001-12-10 | 2012-12-13 | Basf Se | Polyurethane und deren Verwendung als Karosserieaußenteile |
| DE102006005648A1 (de) * | 2006-02-08 | 2007-08-09 | Deutsche Titan Gmbh | Verfahren zum Erzeugen einer Schutzschicht auf einem aus einem Titan-basierten Werkstoff gefertigten Produkt |
| NL1035148C2 (nl) * | 2008-03-04 | 2009-09-07 | Erik Jeroen Eenkhoorn | Werkwijze en systeem voor het beperken van de afname van het drijfvermogen van een vaartuig. |
| US7926565B2 (en) | 2008-10-13 | 2011-04-19 | Baker Hughes Incorporated | Shape memory polyurethane foam for downhole sand control filtration devices |
| US8365833B2 (en) | 2010-03-26 | 2013-02-05 | Baker Hughes Incorporated | Variable Tg shape memory polyurethane for wellbore devices |
| US9068437B2 (en) | 2010-03-26 | 2015-06-30 | Baker Hughes Incorporated | Variable Tg shape memory materials for wellbore devices |
| JP5877131B2 (ja) * | 2012-06-29 | 2016-03-02 | 第一工業製薬株式会社 | ポリウレタン樹脂形成性組成物及びポリウレタン樹脂 |
| WO2015050811A1 (en) * | 2013-10-02 | 2015-04-09 | Dow Global Technologies Llc | Sprayable polyurethane based protective coating |
| WO2017083380A1 (en) | 2015-11-12 | 2017-05-18 | Dow Global Technologies Llc | High molecular weight hydrophobic polyol |
| EP3464407A1 (en) * | 2016-05-31 | 2019-04-10 | Dow Global Technologies LLC | Low cathodic disbondment coating compositions |
| CN106854270A (zh) * | 2016-12-30 | 2017-06-16 | 山东诺威聚氨酯股份有限公司 | 多硬度聚氨酯弹性体及其制备方法 |
| CN119507077B (zh) * | 2024-12-16 | 2025-10-17 | 江南大学 | 一种高强度、可编织的导电疏水聚氨酯共晶凝胶纤维及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169934A (en) | 1961-09-05 | 1965-02-16 | Dow Chemical Co | Rigid butylene-ethylene-ether type polyurethane foams |
| US3274134A (en) * | 1961-09-14 | 1966-09-20 | Ramos Thomas | Very soft urethane vulcanizates which comprise a fully saturated urethane prepolymer and an organotin compound |
| US3634306A (en) | 1967-09-01 | 1972-01-11 | Textron Inc | Moisture-curing polyurethanes soluble in mineral spirits |
| US4301110A (en) | 1980-08-25 | 1981-11-17 | Texaco Inc. | Rim elastomers with improved heat distortion and tear properties |
| US4374209A (en) | 1980-10-01 | 1983-02-15 | Interchem International S.A. | Polymer-modified polyols useful in polyurethane manufacture |
| US4745170A (en) * | 1985-07-25 | 1988-05-17 | The Dow Chemical Company | Polyurethane elastomers from EO/BO polyether polyols |
| DE4104199A1 (de) * | 1991-02-12 | 1992-08-13 | Basf Ag | Verfahren zur herstellung von polyurethan-elastomeren und hierfuer geeignete mischungen aus polyoxybutylen-polyoxyalkylen-glykolen und glycidylverbindungen |
| US5317076A (en) | 1993-04-12 | 1994-05-31 | Texaco Chemical Co. | Polyurea elastomer with reduced moisture vapor transmission |
| FR2764893A1 (fr) | 1997-06-20 | 1998-12-24 | Roland Alexandre Ganga | Elastomeres polyurethannes-polyurees a tres haute tenue en temperature et/ou ignifuges |
| JP3936065B2 (ja) * | 1998-04-15 | 2007-06-27 | 中外商工株式会社 | 土舗装材用結合剤組成物、土舗装材、自然土舗装方法、及び土舗装体 |
-
2000
- 2000-02-23 US US09/913,816 patent/US6613864B1/en not_active Expired - Fee Related
- 2000-02-23 AU AU32406/00A patent/AU3240600A/en not_active Abandoned
- 2000-02-23 EP EP00910288A patent/EP1161472B1/en not_active Expired - Lifetime
- 2000-02-23 AT AT00910288T patent/ATE230769T1/de not_active IP Right Cessation
- 2000-02-23 KR KR1020017010628A patent/KR100602805B1/ko not_active Expired - Fee Related
- 2000-02-23 CN CNB008046263A patent/CN1152071C/zh not_active Expired - Fee Related
- 2000-02-23 WO PCT/US2000/004550 patent/WO2000050484A1/en not_active Ceased
- 2000-02-23 DE DE60001154T patent/DE60001154T2/de not_active Expired - Lifetime
- 2000-02-23 ES ES00910288T patent/ES2190404T3/es not_active Expired - Lifetime
- 2000-02-23 CA CA002362141A patent/CA2362141C/en not_active Expired - Fee Related
- 2000-02-23 JP JP2000601060A patent/JP2002537455A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1161472A1 (en) | 2001-12-12 |
| US6613864B1 (en) | 2003-09-02 |
| CN1152071C (zh) | 2004-06-02 |
| KR20010102299A (ko) | 2001-11-15 |
| DE60001154D1 (en) | 2003-02-13 |
| JP2002537455A (ja) | 2002-11-05 |
| WO2000050484A1 (en) | 2000-08-31 |
| AU3240600A (en) | 2000-09-14 |
| CN1342177A (zh) | 2002-03-27 |
| CA2362141A1 (en) | 2000-08-31 |
| ES2190404T3 (es) | 2003-08-01 |
| CA2362141C (en) | 2009-05-26 |
| ATE230769T1 (de) | 2003-01-15 |
| KR100602805B1 (ko) | 2006-07-20 |
| EP1161472B1 (en) | 2003-01-08 |
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