CA1165929A - Stable emulsions of polyols and crosslinkers for polyurethanes - Google Patents
Stable emulsions of polyols and crosslinkers for polyurethanesInfo
- Publication number
- CA1165929A CA1165929A CA000376810A CA376810A CA1165929A CA 1165929 A CA1165929 A CA 1165929A CA 000376810 A CA000376810 A CA 000376810A CA 376810 A CA376810 A CA 376810A CA 1165929 A CA1165929 A CA 1165929A
- Authority
- CA
- Canada
- Prior art keywords
- molecular weight
- ethylene oxide
- polyol
- emulsion
- pbw
- 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
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 33
- 150000003077 polyols Chemical class 0.000 title claims abstract description 33
- 239000000839 emulsion Substances 0.000 title claims abstract description 27
- 239000004814 polyurethane Substances 0.000 title claims abstract description 7
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 7
- 239000004971 Cross linker Substances 0.000 title description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 71
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 34
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000002009 diols Chemical class 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 229920001400 block copolymer Polymers 0.000 claims description 6
- 239000004970 Chain extender Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 22
- 229920001577 copolymer Polymers 0.000 abstract description 6
- 229920003023 plastic Polymers 0.000 abstract description 3
- 239000004033 plastic Substances 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 27
- 238000010107 reaction injection moulding Methods 0.000 description 20
- 229920000570 polyether Polymers 0.000 description 16
- 239000004721 Polyphenylene oxide Substances 0.000 description 15
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 229920001983 poloxamer Polymers 0.000 description 7
- 229920006389 polyphenyl polymer Polymers 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 propylene, butylene Chemical group 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Natural products O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- 241000143957 Vanessa atalanta Species 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229920005676 ethylene-propylene block copolymer Polymers 0.000 description 1
- 210000003195 fascia Anatomy 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960005419 nitrogen Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 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
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 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 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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
- C08G18/65—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
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
-
- 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
- C08G2130/00—Compositions of compatibilising agents used in mixtures of high-molecular-weight compounds having active hydrogen with other compounds having active hydrogen
-
- 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
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US149,287 | 1980-05-12 | ||
| US06/149,287 US4273884A (en) | 1980-05-12 | 1980-05-12 | Stable emulsions of polyols and crosslinkers for polyurethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1165929A true CA1165929A (en) | 1984-04-17 |
Family
ID=22529575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000376810A Expired CA1165929A (en) | 1980-05-12 | 1981-05-04 | Stable emulsions of polyols and crosslinkers for polyurethanes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4273884A (en:Method) |
| JP (1) | JPS5915335B2 (en:Method) |
| BE (1) | BE888102A (en:Method) |
| CA (1) | CA1165929A (en:Method) |
| DE (1) | DE3112492A1 (en:Method) |
| FR (1) | FR2481946A1 (en:Method) |
| GB (1) | GB2075997B (en:Method) |
| IT (1) | IT1136969B (en:Method) |
| MX (1) | MX7255E (en:Method) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57119915A (en) * | 1981-01-16 | 1982-07-26 | Bridgestone Corp | Preparation of urethane modified isocyanurate foam |
| DE3126517A1 (de) * | 1981-07-04 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls zellhaltigen polyurethan-elastomeren |
| US4362823A (en) * | 1981-08-21 | 1982-12-07 | Manville Service Corporation | Method and composition for closed cell foam formation |
| DE3219822A1 (de) | 1982-05-26 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | Einphasig lagerstabile, salzhaltige polyolkompositionen mit hohem ethylenglykol- oder butandiol-anteil und ihre verwendung zur herstellung von polyurethanen |
| DE3219759A1 (de) * | 1982-05-26 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | Einphasig lagerstabile polyolkompositionen mit hohem ethylenglykol-anteil und ihre verwendung zur herstellung von polyurethanen |
| US4385133A (en) * | 1982-06-07 | 1983-05-24 | The Upjohn Company | Novel compositions and process |
| US4578412A (en) * | 1983-07-05 | 1986-03-25 | Texaco Inc. | Extended amine curing agents [and epoxy resins cured therewith] |
| US4552933A (en) * | 1983-07-05 | 1985-11-12 | Texaco Inc. | Extended amine curing agents and epoxy resins cured therewith |
| US4514530A (en) * | 1983-07-05 | 1985-04-30 | Texaco Inc. | Modified amine curing agents and epoxy resins cured therewith |
| US4485031A (en) * | 1983-09-12 | 1984-11-27 | The Dow Chemical Company | Compatible mixtures of aminated polyether polyols and low molecular weight glycols |
| US4485032A (en) * | 1983-09-12 | 1984-11-27 | The Dow Chemical Company | Compatible polyol blends |
| DE3347574A1 (de) * | 1983-12-30 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | Einphasig lagerstabile, salzhaltige gemische und ihre verwendung zur herstellung von polyurethanen |
| US4661529A (en) * | 1984-08-09 | 1987-04-28 | The Dow Chemical Company | Polyurethane and urethane-modified isocyanurate foams and a polyol composition useful in their preparation |
| JPS6197935U (en:Method) * | 1984-12-03 | 1986-06-23 | ||
| JPS61171720A (ja) * | 1985-01-24 | 1986-08-02 | Sanyo Chem Ind Ltd | ポリウレタンの製法 |
| US4673696A (en) * | 1986-07-03 | 1987-06-16 | Ashland Oil, Inc. | Thermoset molding compositions |
| US5103062A (en) * | 1987-04-10 | 1992-04-07 | Texaco Inc. | Modified normally liquid, water-soluble polyoxyalkylene polyamines |
| GB9028096D0 (en) * | 1990-12-27 | 1991-02-13 | Ici Plc | Isocyanate-reactive compositions |
| DE4138246A1 (de) * | 1991-11-21 | 1993-05-27 | Bayer Ag | Zweikomponenten-polyurethan-reaktivmassen |
| US9045718B2 (en) | 2007-04-09 | 2015-06-02 | Innovation Services, Inc. | Residue cleaning composition and method |
| WO2015009926A1 (en) * | 2013-07-19 | 2015-01-22 | Innovation Services, Inc. | Pretreatment composition, residue cleaning composition, and method of use |
| CN111253734B (zh) * | 2020-01-23 | 2022-08-05 | 上海锦湖日丽塑料有限公司 | 一种高阻尼耐热老化聚酰胺组合物及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328320A (en) * | 1963-02-25 | 1967-06-27 | Ici Ltd | Manufacture of flexible polyurethane foams utilizing polyether-polyisocyanate dispersion |
| FR1487457A (fr) * | 1966-05-26 | 1967-07-07 | Naphtachimie Sa | Mousses de polyuréthane |
| US3489698A (en) * | 1967-05-03 | 1970-01-13 | Union Carbide Corp | Stable emulsions of incompatible polyols containing ethylene oxide-propylene oxide block copolymers as emulsifiers |
| DE1694247A1 (de) * | 1968-02-17 | 1971-06-09 | Bayer Ag | Verfahren zur Herstellung von elastischen Formkoerpern mit kompakter Oberflaeche aus Polyurethanen |
| US3857800A (en) * | 1970-06-19 | 1974-12-31 | Dunlop Holdings Ltd | Flexible polyurethane foams prepared from a mixture of polyether polyols |
| FR2268036A1 (en) * | 1974-04-19 | 1975-11-14 | Naphtachimie Sa | Polyurethane soft foams - obtd. from particular polyether polyols, polyisocyantes and crosslinking agents |
| US3945939A (en) * | 1974-05-20 | 1976-03-23 | The Dow Chemical Company | Mixtures of high and low molecular weight polyols resistant to phase separation |
-
1980
- 1980-05-12 US US06/149,287 patent/US4273884A/en not_active Expired - Lifetime
-
1981
- 1981-02-20 GB GB8105510A patent/GB2075997B/en not_active Expired
- 1981-03-24 FR FR8105839A patent/FR2481946A1/fr active Granted
- 1981-03-24 BE BE0/204243A patent/BE888102A/fr not_active IP Right Cessation
- 1981-03-27 MX MX819382U patent/MX7255E/es unknown
- 1981-03-27 IT IT20780/81A patent/IT1136969B/it active
- 1981-03-30 DE DE19813112492 patent/DE3112492A1/de not_active Withdrawn
- 1981-04-21 JP JP56059352A patent/JPS5915335B2/ja not_active Expired
- 1981-05-04 CA CA000376810A patent/CA1165929A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3112492A1 (de) | 1981-12-24 |
| US4273884A (en) | 1981-06-16 |
| GB2075997A (en) | 1981-11-25 |
| FR2481946B1 (en:Method) | 1984-04-13 |
| FR2481946A1 (fr) | 1981-11-13 |
| JPS5915335B2 (ja) | 1984-04-09 |
| JPS575750A (en) | 1982-01-12 |
| MX7255E (es) | 1988-02-26 |
| IT1136969B (it) | 1986-09-03 |
| GB2075997B (en) | 1983-06-08 |
| BE888102A (fr) | 1981-09-24 |
| IT8120780A0 (it) | 1981-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |