CA2266623C - Light-stable elastomeric polyurethane mouldings and process for the production thereof - Google Patents
Light-stable elastomeric polyurethane mouldings and process for the production thereof Download PDFInfo
- Publication number
- CA2266623C CA2266623C CA002266623A CA2266623A CA2266623C CA 2266623 C CA2266623 C CA 2266623C CA 002266623 A CA002266623 A CA 002266623A CA 2266623 A CA2266623 A CA 2266623A CA 2266623 C CA2266623 C CA 2266623C
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- weight
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- isocyanate
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 58
- 230000008569 process Effects 0.000 title claims abstract description 57
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 31
- 238000000465 moulding Methods 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 92
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 239000012948 isocyanate Substances 0.000 claims abstract description 50
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 42
- 238000010107 reaction injection moulding Methods 0.000 claims abstract description 41
- 239000003999 initiator Substances 0.000 claims abstract description 37
- 239000011541 reaction mixture Substances 0.000 claims abstract description 32
- 239000013638 trimer Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 239000006096 absorbing agent Substances 0.000 claims abstract description 13
- 238000005538 encapsulation Methods 0.000 claims abstract description 13
- 239000000049 pigment Substances 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
- 239000004970 Chain extender Substances 0.000 claims abstract description 9
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 8
- 230000001413 cellular effect Effects 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 4
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 4
- 229920005862 polyol Polymers 0.000 claims description 53
- 150000003077 polyols Chemical class 0.000 claims description 51
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 31
- -1 polytetramethylene Polymers 0.000 claims description 23
- 239000004606 Fillers/Extenders Substances 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 11
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 10
- 239000004971 Cross linker Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 238000007654 immersion Methods 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000004604 Blowing Agent Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 2
- 229920001971 elastomer Polymers 0.000 description 28
- 239000000806 elastomer Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 26
- 239000011521 glass Substances 0.000 description 23
- 239000003292 glue Substances 0.000 description 15
- 230000009257 reactivity Effects 0.000 description 15
- 229920003225 polyurethane elastomer Polymers 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 8
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 8
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 230000000007 visual effect Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920005903 polyol mixture Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical group CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- VQPKAMAVKYTPLB-UHFFFAOYSA-N lead;octanoic acid Chemical compound [Pb].CCCCCCCC(O)=O VQPKAMAVKYTPLB-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000004707 phenolate Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 101150116295 CAT2 gene Proteins 0.000 description 1
- 101100392078 Caenorhabditis elegans cat-4 gene Proteins 0.000 description 1
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 101100005280 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-3 gene Proteins 0.000 description 1
- 101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- JDIBGQFKXXXXPN-UHFFFAOYSA-N bismuth(3+) Chemical class [Bi+3] JDIBGQFKXXXXPN-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical class [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
-
- 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
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0016—Foam properties semi-rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/0066—≥ 150kg/m3
-
- 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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96202738 | 1996-10-01 | ||
| EP96202738.9 | 1996-10-01 | ||
| PCT/BE1997/000112 WO1998014492A1 (en) | 1996-10-01 | 1997-10-01 | Light-stable elastomeric polyurethane mouldings and process for the production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2266623A1 CA2266623A1 (en) | 1998-04-09 |
| CA2266623C true CA2266623C (en) | 2009-12-15 |
Family
ID=8224452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002266623A Expired - Fee Related CA2266623C (en) | 1996-10-01 | 1997-10-01 | Light-stable elastomeric polyurethane mouldings and process for the production thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6242555B1 (en, 2012) |
| EP (1) | EP0929586B1 (en, 2012) |
| JP (1) | JP3911030B2 (en, 2012) |
| KR (1) | KR100551978B1 (en, 2012) |
| AT (1) | ATE200683T1 (en, 2012) |
| AU (1) | AU4446697A (en, 2012) |
| BR (1) | BR9712182A (en, 2012) |
| CA (1) | CA2266623C (en, 2012) |
| CZ (1) | CZ299115B6 (en, 2012) |
| DE (1) | DE69704626T2 (en, 2012) |
| DK (1) | DK0929586T3 (en, 2012) |
| ES (1) | ES2157600T3 (en, 2012) |
| HU (1) | HU223496B1 (en, 2012) |
| ID (1) | ID21506A (en, 2012) |
| IN (1) | IN1997CH00157A (en, 2012) |
| MX (1) | MX216281B (en, 2012) |
| PL (1) | PL192282B1 (en, 2012) |
| PT (1) | PT929586E (en, 2012) |
| RU (1) | RU2201940C2 (en, 2012) |
| SK (1) | SK285340B6 (en, 2012) |
| WO (1) | WO1998014492A1 (en, 2012) |
| ZA (1) | ZA978803B (en, 2012) |
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| EP0995568A1 (en) * | 1998-10-21 | 2000-04-26 | Recticel | Method for manufacturing a multilayered moulded synthetic part and thus obtained part |
| JP4320846B2 (ja) * | 1999-06-10 | 2009-08-26 | 旭硝子株式会社 | 光硬化性組成物 |
| JP4540079B2 (ja) * | 2000-04-28 | 2010-09-08 | Ｊｓｒ株式会社 | 光ファイバ用硬化性樹脂組成物およびその硬化物 |
| EP1177949A1 (en) * | 2000-08-01 | 2002-02-06 | Recticel | Method for manufacturing a trim part for the interior of an automobile vehicle or at least a skin therefor |
| DE10142296C1 (de) | 2001-08-29 | 2003-02-13 | Bayer Ag | Polyurethanelastomere, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6919486B2 (en) * | 2001-12-21 | 2005-07-19 | Basf Corporation | Polyetherols produced using aluminium phosphonate catalysts |
| US20030213189A1 (en) * | 2002-05-16 | 2003-11-20 | Goldman Arthur S. | Thermoplastic polymer extrusion bending |
| AU2003238574A1 (en) * | 2002-06-21 | 2004-01-06 | Recticel | Micro-cellular or non-cellular light-stable polyurethane material and method for the production thereof |
| US6825238B2 (en) * | 2003-01-29 | 2004-11-30 | Air Products And Chemicals, Inc. | Low acid organometallic catalyst for the production of flexible, semi-flexible and rigid polyurethane foams |
| US7878373B2 (en) | 2003-04-18 | 2011-02-01 | Mayex Usa Kft. | Dispensing cap |
| WO2005089085A2 (en) | 2003-07-14 | 2005-09-29 | Rhodia Inc | Improved color stability of isocyanates |
| US7296388B2 (en) | 2003-08-12 | 2007-11-20 | Valentz Arthur J | Skylight having a molded plastic frame |
| EP1510322A1 (en) | 2003-08-27 | 2005-03-02 | Recticel | Method for manufacturing a composite trim part for the interior of an automotive vehicle |
| US20050143478A1 (en) * | 2003-12-24 | 2005-06-30 | Kao Corporation | Catalyst for preparing polyurethane |
| DE102004009740A1 (de) * | 2004-02-25 | 2005-09-15 | Basf Ag | Zinn- und Übergangsmetallfreie Polyurethanschaumstoffe |
| US7021498B2 (en) | 2004-04-06 | 2006-04-04 | Advanced Controls And Engineering | Urethane spray gun assembly |
| MXPA06013028A (es) * | 2004-05-12 | 2008-03-11 | Nauer Fritz Ag | Espuma de poliuretano flexible. |
| US7268170B2 (en) * | 2004-10-13 | 2007-09-11 | Bayer Materialscience Llc | Foam modifier, foams prepared from this novel foam modifier and a process for the preparation of these foams |
| EP1657267A1 (en) * | 2004-11-10 | 2006-05-17 | INSA (Institut National des Sciences Appliqées) | Two-part polyisocyanate/polyol composition and its use for making casted products, in particular ophthalmic lenses |
| US8188208B2 (en) * | 2005-01-13 | 2012-05-29 | Bayer Materialscience Llc | Solid polyurethane elastomers which exhibit reduced dimensional shrinkage |
| US20060160977A1 (en) * | 2005-01-14 | 2006-07-20 | Jung-Shun Ou | Prescription for preparation of non-yellowing polyurethane foam |
| CA2596870A1 (en) * | 2005-02-04 | 2006-08-10 | The Procter & Gamble Company | Absorbent structure with improved water-absorbing material |
| US20060225776A1 (en) * | 2005-04-08 | 2006-10-12 | Portable Pipe Hangers, Inc. | Skylight solar panel assembly |
| PL1757446T3 (pl) * | 2005-08-23 | 2011-10-31 | Recticel Automobilsysteme Gmbh | Płytowy laminat i powłoka do wytwarzania takiego laminatu |
| US20070142607A1 (en) * | 2005-12-15 | 2007-06-21 | Bayer Materialscience Llc | Weather resistant polyurethane elastomer |
| US7772353B2 (en) * | 2005-12-15 | 2010-08-10 | Bayer Materialscience Llc | Fast curing aliphatic RIM elastomers |
| US20070142601A1 (en) * | 2005-12-15 | 2007-06-21 | Bayer Materialscience Llc | RIM elastomers based on isocyanurates of isophorone diisocyanate and prepolymers thereof |
| US20070142610A1 (en) * | 2005-12-15 | 2007-06-21 | Harasin Stephen J | Polyurethane elastomers comprising allophanate modified isocyanates |
| US20070185302A1 (en) * | 2006-02-08 | 2007-08-09 | Bayer Materialscience Llc | Polyurethane elastomers comprising allophanate modified isocyanates |
| DE102006016617B4 (de) * | 2006-04-06 | 2008-02-28 | Carl Freudenberg Kg | Polyurethanformteil, Verfahren zu dessen Herstellung und dessen Verwendung |
| RU2565080C2 (ru) * | 2006-05-30 | 2015-10-20 | Ректисел Аутомобилзюстем Гмбх | Способ изготовления гибкой эластомерной полиуретановой кожи |
| WO2007144292A1 (en) * | 2006-06-14 | 2007-12-21 | Huntsman International Llc | Cross-linkable thermoplastic polyurethanes |
| WO2008025561A1 (en) * | 2006-08-31 | 2008-03-06 | Pilkington Italia S.P.A. | Method for encapsulating the edge of a glass sheet |
| DE102007005960A1 (de) * | 2007-02-07 | 2008-08-14 | Bayer Materialscience Ag | Ruß-gefüllte Polyurethane mit hoher Dielektrizitätskonstante und Durchschlagsfestigkeit |
| JP5368716B2 (ja) * | 2007-03-01 | 2013-12-18 | 花王株式会社 | ポリウレタン成形品の製造方法 |
| EP2009039A1 (en) | 2007-06-27 | 2008-12-31 | Universiteit Gent | Functionalised polyurethanes |
| WO2009015149A1 (en) * | 2007-07-23 | 2009-01-29 | Dow Global Technologies Inc. | Two part polyurethane curable composition having substantially consistent g-modulus across the range of use temperatures |
| MX2010002339A (es) * | 2007-08-27 | 2010-04-30 | Dow Global Technologies Inc | Catalisis de espumas viscoelasticas con sales de bismuto. |
| JP5154187B2 (ja) * | 2007-10-03 | 2013-02-27 | アイカ工業株式会社 | 上水道用表面ウレタン樹脂組成物 |
| US8722752B2 (en) | 2007-10-15 | 2014-05-13 | Mitsui Chemicals, Inc. | Polyurethane resin |
| WO2009051104A1 (ja) * | 2007-10-15 | 2009-04-23 | Mitsui Chemicals Polyurethanes, Inc. | 粒子状ポリウレタン樹脂組成物およびその成形品 |
| US20100305294A1 (en) * | 2007-11-28 | 2010-12-02 | Mitsui Chemicals, Inc. | Polyurethane resin composition for reaction injection molding and molded article |
| DE102008008391A1 (de) * | 2008-02-09 | 2009-08-13 | Bayer Materialscience Ag | Geschäumte, lichtechte Polyurethanformteile |
| CN101412798B (zh) | 2008-11-21 | 2011-08-10 | 优洁（亚洲）有限公司 | 软质聚氨酯低回弹泡沫及其制备方法 |
| DE102009005712A1 (de) | 2009-01-22 | 2010-07-29 | Bayer Materialscience Ag | Polyurethanvergussmassen |
| JP5267207B2 (ja) * | 2009-02-25 | 2013-08-21 | 宇部興産株式会社 | フェノール性水酸基含有ポリウレタン |
| JP2010214298A (ja) | 2009-03-17 | 2010-09-30 | Japan Gore Tex Inc | 透湿性隔膜材料 |
| EP2269794A1 (en) | 2009-07-02 | 2011-01-05 | RECTICEL Automobilsysteme GmbH | Method of making an elastomeric skin and skin obtained by that method |
| CN101768251B (zh) * | 2009-12-31 | 2012-08-08 | 南京汇科高分子材料有限公司 | 用于汽车玻璃包边的聚氨酯弹性体及其制备方法 |
| EP2365012A1 (en) * | 2010-03-05 | 2011-09-14 | RECTICEL Automobilsysteme GmbH | Method for producing a skin layer of a flexible, elastomeric, thermoset, phase-separated polyurethane material |
| WO2012020027A1 (de) | 2010-08-12 | 2012-02-16 | Bayer Materialscience Ag | Lichtechte polyurethane und ihre verwendung |
| ES2527249T3 (es) | 2010-09-07 | 2015-01-21 | Bayer Intellectual Property Gmbh | Piezas de moldeo de poliuretano espumadas, aligeradas |
| EP2522684A1 (en) | 2011-05-12 | 2012-11-14 | Recticel | Method for functionalising a thermoset isocyanate-based polymeric solid material. |
| KR101319684B1 (ko) | 2011-06-07 | 2013-10-17 | 금호미쓰이화학 주식회사 | 내열성 변성 이소시아네이트 조성물 및 이를 포함하는 내열성을 갖는 파이프 단열용 폴리우레탄 발포체 조성물 및 그 발포방법 |
| EP2679380A1 (en) | 2012-06-28 | 2014-01-01 | RECTICEL Automobilsysteme GmbH | Method for manufacturing a flexible skin having at least one insert adhered thereto. |
| ITMI20131026A1 (it) * | 2013-06-20 | 2014-12-20 | Dow Global Technologies Llc | Processo per la produzione di un espanso poliuretanico che utilizza un catalizzatore tetraalchilstannossi |
| ES2560475T3 (es) | 2013-04-30 | 2016-02-19 | Webasto SE | Método y molde para producir un conjunto de panel |
| DE102013022173B4 (de) | 2013-12-23 | 2017-03-30 | Gt Elektrotechnische Produkte Gmbh | Polyurethan-Elastomere auf der Basis von Polyetheralkoholgemischen und trimerisierten Diisocyanaten |
| EP2923812A1 (en) | 2014-03-25 | 2015-09-30 | Johan Ria Hugo Van Dyck | Method and mould for producing a panel assembly |
| EP3009248A1 (en) | 2014-10-13 | 2016-04-20 | RECTICEL Automobilsysteme GmbH | Method for producing an elastomeric skin having a grained surface |
| TWI713479B (zh) * | 2014-12-15 | 2020-12-21 | 美商陶氏全球科技責任有限公司 | 黏著劑組合物 |
| DE102015218869B4 (de) | 2015-09-30 | 2017-10-26 | Lisa Dräxlmaier GmbH | Verfahren und Vorrichtung zur Herstellung eines Zuschnitts einer Sprühhaut |
| PL3559070T3 (pl) * | 2017-04-28 | 2020-11-16 | Recticel Automobilsysteme Gmbh | Pokrycia z kompozytu elastomeru poliuretanowego |
| CN110799502B (zh) * | 2017-07-07 | 2022-12-30 | 奇钛科技股份有限公司 | 反应型紫外光吸收剂及其应用 |
| US11046850B2 (en) | 2017-09-27 | 2021-06-29 | Evonik Operations Gmbh | Mixed metal catalyst compositions and methods for making polyurethane foam |
| US20210388150A1 (en) | 2018-11-19 | 2021-12-16 | Covestro Intellectual Property Gmbh & Co. Kg | A process for producing a polyurethane elastomer |
| CN111196871A (zh) * | 2018-11-19 | 2020-05-26 | 科思创德国股份有限公司 | 一种制备聚氨酯弹性体的方法 |
| CN110183843B (zh) * | 2019-05-16 | 2021-12-14 | 美瑞新材料股份有限公司 | 一种耐黄变的热塑性聚氨酯发泡材料及其制备方法 |
| WO2021130104A1 (en) * | 2019-12-24 | 2021-07-01 | Covestro Deutschland Ag | Flexible foam |
| WO2021144285A1 (en) | 2020-01-16 | 2021-07-22 | Ascorium Gmbh | Skin for a vehicle interior trim part comprising a light source |
| MX2022007400A (es) | 2020-01-16 | 2022-09-19 | Ascorium Gmbh | Cubierta para una pieza de revestimiento interior de un vehiculo que contiene un elemento operativo. |
| PL3862375T3 (pl) * | 2020-02-10 | 2025-02-24 | Indresmat Bv | Zastosowanie izocyjanianu alifatycznego jako środka ograniczającego toksyczne opary w piankach poliuretanowych |
| JP7469611B2 (ja) * | 2020-02-27 | 2024-04-17 | 東ソー株式会社 | ウレタンプレポリマー組成物 |
| JP7413927B2 (ja) * | 2020-05-26 | 2024-01-16 | 東ソー株式会社 | ウレタンプレポリマー組成物 |
| EP4323421A1 (en) * | 2021-04-13 | 2024-02-21 | Basf Se | Non-solvent pu system, an artificial leather comprising the same and a process for producing the artificial leather |
| PE20242279A1 (es) * | 2021-07-13 | 2024-11-29 | Akzo Nobel Coatings Int Bv | Composicion de adhesivo curable con humedad de un componente |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931381A (en) * | 1970-09-04 | 1976-01-06 | The General Tire & Rubber Company | Mold release method for polyurethane integral-skin foam |
| LU81024A1 (fr) * | 1979-03-09 | 1980-09-24 | Prb Sa | Procede pour la preparation de polyurethanne a peau integrale et polyurethanne obtenu |
| DE2914134A1 (de) * | 1979-04-07 | 1980-10-23 | Bayer Ag | Verfahren zur herstellung von polyurethan-schaumstoffen |
| US4452924A (en) * | 1983-05-05 | 1984-06-05 | Mobay Chemical Corporation | Flexible polyurethane foams having improved load bearing characteristics |
| SU1275018A1 (ru) * | 1985-03-15 | 1986-12-07 | Казанский Ордена Трудового Красного Знамени Химико-Технологический Институт Им.С.М.Кирова | Способ получени эластичных пенополиуретанов |
| EP0275010B1 (de) * | 1987-01-14 | 1991-11-21 | Bayer Ag | Verfahren zur Herstellung von Polyurethan-Formteilen |
| US5656677A (en) * | 1989-01-20 | 1997-08-12 | Recticel | Method for preparing and applying a sprayable, light stable polyurethane |
| US5100997A (en) * | 1990-05-29 | 1992-03-31 | Olin Corporation | Preparation of elastomers using high molecular weight polyols or polyamines, said polyols prepared using a double metal cyanide complex catalyst |
| US5502147A (en) * | 1993-12-21 | 1996-03-26 | Bayer Corporation | Aliphatic rim elastomers |
| CA2174305C (en) * | 1995-06-07 | 2007-07-03 | Ronald A. Cageao | Method of producing gaskets from polyurethane/urea compositions and gaskets produced therefrom |
-
1997
- 1997-09-30 IN IN157CH1997 patent/IN1997CH00157A/en unknown
- 1997-10-01 ID IDW990286A patent/ID21506A/id unknown
- 1997-10-01 BR BR9712182-7A patent/BR9712182A/pt not_active IP Right Cessation
- 1997-10-01 SK SK400-99A patent/SK285340B6/sk not_active IP Right Cessation
- 1997-10-01 JP JP51606098A patent/JP3911030B2/ja not_active Expired - Lifetime
- 1997-10-01 US US09/068,516 patent/US6242555B1/en not_active Expired - Lifetime
- 1997-10-01 DE DE69704626T patent/DE69704626T2/de not_active Expired - Lifetime
- 1997-10-01 HU HU0000054A patent/HU223496B1/hu not_active IP Right Cessation
- 1997-10-01 RU RU99108990/04A patent/RU2201940C2/ru not_active IP Right Cessation
- 1997-10-01 MX MX9903192A patent/MX216281B/es not_active IP Right Cessation
- 1997-10-01 ES ES97942719T patent/ES2157600T3/es not_active Expired - Lifetime
- 1997-10-01 PT PT97942719T patent/PT929586E/pt unknown
- 1997-10-01 CA CA002266623A patent/CA2266623C/en not_active Expired - Fee Related
- 1997-10-01 WO PCT/BE1997/000112 patent/WO1998014492A1/en active IP Right Grant
- 1997-10-01 AU AU44466/97A patent/AU4446697A/en not_active Abandoned
- 1997-10-01 DK DK97942719T patent/DK0929586T3/da active
- 1997-10-01 PL PL332552A patent/PL192282B1/pl not_active IP Right Cessation
- 1997-10-01 ZA ZA9708803A patent/ZA978803B/xx unknown
- 1997-10-01 EP EP97942719A patent/EP0929586B1/en not_active Expired - Lifetime
- 1997-10-01 AT AT97942719T patent/ATE200683T1/de active
- 1997-10-01 KR KR1019997002826A patent/KR100551978B1/ko not_active Expired - Lifetime
- 1997-10-01 CZ CZ0109299A patent/CZ299115B6/cs not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX216281B (es) | 2003-09-09 |
| DK0929586T3 (da) | 2001-08-13 |
| DE69704626D1 (de) | 2001-05-23 |
| JP2001501241A (ja) | 2001-01-30 |
| KR100551978B1 (ko) | 2006-02-20 |
| ATE200683T1 (de) | 2001-05-15 |
| CZ299115B6 (cs) | 2008-04-23 |
| KR20000048830A (ko) | 2000-07-25 |
| HUP0000054A3 (en) | 2000-09-28 |
| HU223496B1 (hu) | 2004-08-30 |
| JP3911030B2 (ja) | 2007-05-09 |
| SK40099A3 (en) | 2000-07-11 |
| EP0929586A1 (en) | 1999-07-21 |
| RU2201940C2 (ru) | 2003-04-10 |
| HUP0000054A2 (hu) | 2000-05-28 |
| US6242555B1 (en) | 2001-06-05 |
| BR9712182A (pt) | 1999-08-31 |
| CZ109299A3 (cs) | 1999-09-15 |
| SK285340B6 (sk) | 2006-11-03 |
| PT929586E (pt) | 2001-09-28 |
| ZA978803B (en) | 1998-04-17 |
| PL192282B1 (pl) | 2006-09-29 |
| MX9903192A (es) | 1999-08-31 |
| EP0929586B1 (en) | 2001-04-18 |
| WO1998014492A1 (en) | 1998-04-09 |
| ES2157600T3 (es) | 2001-08-16 |
| CA2266623A1 (en) | 1998-04-09 |
| DE69704626T2 (de) | 2001-11-08 |
| ID21506A (id) | 1999-06-17 |
| AU4446697A (en) | 1998-04-24 |
| IN1997CH00157A (en, 2012) | 2006-06-09 |
| PL332552A1 (en) | 1999-09-13 |
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Effective date: 20141001 |