CA2411086C - Liquid stable mdi prepolymers and liquid stable curative systems suitable for room temperature casting which yield high performance urethane elastomers - Google Patents
Liquid stable mdi prepolymers and liquid stable curative systems suitable for room temperature casting which yield high performance urethane elastomers Download PDFInfo
- Publication number
- CA2411086C CA2411086C CA 2411086 CA2411086A CA2411086C CA 2411086 C CA2411086 C CA 2411086C CA 2411086 CA2411086 CA 2411086 CA 2411086 A CA2411086 A CA 2411086A CA 2411086 C CA2411086 C CA 2411086C
- Authority
- CA
- Canada
- Prior art keywords
- prepolymer
- weight
- polyoxypropylene
- equivalent weight
- room temperature
- 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 - Fee Related
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 53
- 229920006311 Urethane elastomer Polymers 0.000 title claims abstract description 11
- 238000005266 casting Methods 0.000 title abstract description 9
- -1 polyoxypropylene Polymers 0.000 claims description 117
- 229920001451 polypropylene glycol Polymers 0.000 claims description 76
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 62
- 150000002009 diols Chemical class 0.000 claims description 49
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 33
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 28
- 238000007872 degassing Methods 0.000 claims description 28
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 13
- 239000004970 Chain extender Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 229920001971 elastomer Polymers 0.000 abstract description 5
- 239000000806 elastomer Substances 0.000 abstract description 5
- 230000000295 complement effect Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 78
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 52
- 239000000203 mixture Substances 0.000 description 48
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- 239000004721 Polyphenylene oxide Substances 0.000 description 35
- 229920000570 polyether Polymers 0.000 description 35
- 238000013019 agitation Methods 0.000 description 29
- 239000004615 ingredient Substances 0.000 description 20
- 239000004971 Cross linker Substances 0.000 description 18
- 239000004814 polyurethane Substances 0.000 description 18
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 18
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- 229920002635 polyurethane Polymers 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000005484 gravity Effects 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 150000004072 triols Chemical class 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920013701 VORANOL™ Polymers 0.000 description 3
- 125000006177 alkyl benzyl group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- KESQFSZFUCZCEI-UHFFFAOYSA-N 2-(5-nitropyridin-2-yl)oxyethanol Chemical compound OCCOC1=CC=C([N+]([O-])=O)C=N1 KESQFSZFUCZCEI-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-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
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical class O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-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
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/593,913 US6830705B1 (en) | 2000-06-14 | 2000-06-14 | Liquid stable MDI prepolymers and liquid stable curative systems suitable for room temperature casting which yield high performance urethane elastomers |
| US09/593,913 | 2000-06-14 | ||
| PCT/US2001/018441 WO2001096435A1 (en) | 2000-06-14 | 2001-06-07 | Liquid stable mdi prepolymers and liquid stable curative systems suitable for room temperature casting which yield high performance urethane elastomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2411086A1 CA2411086A1 (en) | 2001-12-20 |
| CA2411086C true CA2411086C (en) | 2008-08-05 |
Family
ID=24376733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2411086 Expired - Fee Related CA2411086C (en) | 2000-06-14 | 2001-06-07 | Liquid stable mdi prepolymers and liquid stable curative systems suitable for room temperature casting which yield high performance urethane elastomers |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6830705B1 (OSRAM) |
| JP (1) | JP4071102B2 (OSRAM) |
| KR (1) | KR100573044B1 (OSRAM) |
| CN (1) | CN1246357C (OSRAM) |
| AU (1) | AU2001275359A1 (OSRAM) |
| CA (1) | CA2411086C (OSRAM) |
| GB (1) | GB2380485B (OSRAM) |
| WO (1) | WO2001096435A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003220550A1 (en) * | 2002-03-29 | 2003-10-20 | Huntsman International Llc | Process for filament winding |
| JP4671105B2 (ja) * | 2005-02-25 | 2011-04-13 | 日本ポリウレタン工業株式会社 | 紙送りロール製造用組成物、紙送りロールおよびその製造方法 |
| JP5642047B2 (ja) * | 2010-12-21 | 2014-12-17 | ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ | 接着剤組成物 |
| CN102174169A (zh) * | 2011-01-30 | 2011-09-07 | 哈尔滨工业大学 | 一种mdi/peg体系的弹性固化剂及其制备方法 |
| US8889630B2 (en) | 2011-12-23 | 2014-11-18 | Carlos Lopez | Method for hair regrowth using Granulocyte-Colony Stimulating Factor |
| KR101204905B1 (ko) | 2012-02-21 | 2012-11-26 | 주식회사 유한인터텍 | 무용제 우레탄형 바인더를 이용한 플로킹 인공피혁 제조방법 및 이를 이용한 가공품 |
| US11738487B2 (en) | 2021-01-22 | 2023-08-29 | Covestro Llc | Processes for making molded flexible foams and flexible foams produced thereby |
| CN114591484B (zh) * | 2022-03-15 | 2023-05-30 | 北京理工大学 | 一种力学性能优异的不发泡聚氨酯弹性体的制备方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE567937A (OSRAM) | 1957-05-23 | |||
| US3161993A (en) | 1963-11-12 | 1964-12-22 | Roto Finish Co | Finishing apparatus and method |
| DE2221756C3 (de) | 1972-05-04 | 1980-06-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von lösungsmittelbeständigen, lichtechten, knick- und reibfesten Polyurethanüberzügen auf textlien Substraten, Leder oder Kunstleder oder von Folien |
| US4134883A (en) | 1977-08-23 | 1979-01-16 | Westinghouse Electric Corp. | Abrasion resistant polyurethane article having a high rolling coefficient of friction |
| US4307544A (en) | 1979-11-28 | 1981-12-29 | Roto-Finish Company, Inc. | Finishing machine with abrasive lined chamber and method of finishing |
| US4294951A (en) | 1980-07-14 | 1981-10-13 | Mitsui-Nisso Corporation | Rapid curing polyurethane elastomer prepared from a diphenylmethanediisocyanate based liquid prepolymer and a curing agent containing a polytetramethylene ether glycol, a diol and an organometallic catalyst |
| US4379904A (en) * | 1980-11-24 | 1983-04-12 | The Upjohn Company | Novel polyurethane product |
| DE3148838A1 (de) | 1981-12-10 | 1983-06-23 | Bayer Ag, 5090 Leverkusen | Verwendung fluessiger, kalthaertender polyurethanbildender komponenten fuer korrosionshemmende, verschleissschuetzende beschichtungen von metall- und kunststoff-flaechen und -formkoerpern sowie von gestein und beton |
| US4385133A (en) * | 1982-06-07 | 1983-05-24 | The Upjohn Company | Novel compositions and process |
| US4520042A (en) | 1983-06-20 | 1985-05-28 | Thermocell Development, Ltd. | High-modulus, flexible urethane coating and method of preparation |
| US4701476A (en) | 1985-12-27 | 1987-10-20 | The Dow Chemical Company | Polyurethane elastomers prepared from high molecular weight prepolymers |
| US4695618A (en) | 1986-05-23 | 1987-09-22 | Ameron, Inc. | Solventless polyurethane spray compositions and method for applying them |
| DE3912531C2 (de) | 1989-04-17 | 1998-08-27 | Basf Ag | Glasklare, heißdampfsterilisierbare, kompakte Polyurethan-Vergußmassen, Verfahren zu ihrer Herstellung und ihre Verwendung, insbesondere für medizinisch technische Artikel |
| US5115007A (en) | 1989-11-30 | 1992-05-19 | Gencorp Inc. | Abrasion resistant polyurethane blend compositions |
| US5130404A (en) | 1991-06-04 | 1992-07-14 | Azon Usa Inc. | Castable thermosetting polyurethane polymer having improved heat stability |
| US5194558A (en) | 1991-09-30 | 1993-03-16 | Xerox Corporation | Disk stacker with novel paddle wheel wiper made of polyether urethane |
| US6376698B1 (en) * | 1991-12-17 | 2002-04-23 | Imperial Chemical Industries Plc | Prepolymers |
| US5621016A (en) | 1992-04-16 | 1997-04-15 | Imperial Chemical Industries Plc | Polyisocyanate compositions and low density flexible polyurethane foams produced therewith |
| US5565498A (en) | 1993-02-02 | 1996-10-15 | Imperial Chemical Industries Plc | Process for making flexible foams |
| US5350778A (en) | 1993-10-28 | 1994-09-27 | Miles Inc. | Polyisocyanate based upon 4,4'- and 2,4'-diphenylmethane diisocyanates and use thereof in a rim process |
| DE69530928T2 (de) | 1994-08-22 | 2003-12-24 | Zeon Corp., Tokio | Gegenstand aus polyurethane in einer tubularen ballon form |
| US5554713A (en) | 1995-01-06 | 1996-09-10 | Azon Usa Inc. | Thermosetting castable and curable polyurethane-urea polymers having improved flow and end-waste characteristics for insulating thermal barriers |
| DE19826398A1 (de) | 1998-06-12 | 1999-12-16 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Elastomern |
-
2000
- 2000-06-14 US US09/593,913 patent/US6830705B1/en not_active Expired - Fee Related
-
2001
- 2001-06-07 AU AU2001275359A patent/AU2001275359A1/en not_active Abandoned
- 2001-06-07 CN CNB018125379A patent/CN1246357C/zh not_active Expired - Fee Related
- 2001-06-07 GB GB0300829A patent/GB2380485B/en not_active Expired - Fee Related
- 2001-06-07 WO PCT/US2001/018441 patent/WO2001096435A1/en not_active Ceased
- 2001-06-07 CA CA 2411086 patent/CA2411086C/en not_active Expired - Fee Related
- 2001-06-07 JP JP2002510567A patent/JP4071102B2/ja not_active Expired - Fee Related
- 2001-11-26 US US09/992,780 patent/US6767985B2/en not_active Expired - Fee Related
-
2002
- 2002-12-14 KR KR1020027017101A patent/KR100573044B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001096435A1 (en) | 2001-12-20 |
| JP4071102B2 (ja) | 2008-04-02 |
| CN1441816A (zh) | 2003-09-10 |
| KR20030010723A (ko) | 2003-02-05 |
| US6767985B2 (en) | 2004-07-27 |
| CA2411086A1 (en) | 2001-12-20 |
| GB2380485A (en) | 2003-04-09 |
| CN1246357C (zh) | 2006-03-22 |
| KR100573044B1 (ko) | 2006-04-25 |
| GB0300829D0 (en) | 2003-02-12 |
| US6830705B1 (en) | 2004-12-14 |
| GB2380485B (en) | 2004-03-24 |
| US20020055604A1 (en) | 2002-05-09 |
| AU2001275359A1 (en) | 2001-12-24 |
| JP2004503628A (ja) | 2004-02-05 |
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| EEER | Examination request | ||
| MKLA | Lapsed |