GB882547A - Improvements in and relating to catalysts for isocyanate reactions - Google Patents
Improvements in and relating to catalysts for isocyanate reactionsInfo
- Publication number
- GB882547A GB882547A GB41186/59A GB4118659A GB882547A GB 882547 A GB882547 A GB 882547A GB 41186/59 A GB41186/59 A GB 41186/59A GB 4118659 A GB4118659 A GB 4118659A GB 882547 A GB882547 A GB 882547A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- compounds
- arsenic
- reactive
- atom
- 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
- 238000006243 chemical reaction Methods 0.000 title abstract 7
- 239000003054 catalyst Substances 0.000 title abstract 4
- 239000012948 isocyanate Substances 0.000 title abstract 4
- 150000002513 isocyanates Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 10
- 229910052785 arsenic Inorganic materials 0.000 abstract 8
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 8
- 150000002894 organic compounds Chemical class 0.000 abstract 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 229920000728 polyester Polymers 0.000 abstract 6
- 229920000570 polyether Polymers 0.000 abstract 6
- 150000003512 tertiary amines Chemical class 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 5
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 229910052787 antimony Inorganic materials 0.000 abstract 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 4
- 229910052797 bismuth Inorganic materials 0.000 abstract 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 4
- 239000007795 chemical reaction product Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 4
- 229920001228 polyisocyanate Polymers 0.000 abstract 4
- 239000005056 polyisocyanate Substances 0.000 abstract 4
- XAZAQTBGMXGTBD-UHFFFAOYSA-N tributylarsane Chemical compound CCCC[As](CCCC)CCCC XAZAQTBGMXGTBD-UHFFFAOYSA-N 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229920000768 polyamine Polymers 0.000 abstract 3
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 abstract 2
- JKCNWCFOTQFHLC-UHFFFAOYSA-N 1-diethylstiborylethane Chemical compound CC[Sb](=O)(CC)CC JKCNWCFOTQFHLC-UHFFFAOYSA-N 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- FVVXWRGARUACNW-UHFFFAOYSA-N 3-methylisoquinoline Chemical compound C1=CC=C2C=NC(C)=CC2=C1 FVVXWRGARUACNW-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical group CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 abstract 2
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001414 amino alcohols Chemical class 0.000 abstract 2
- 229920001400 block copolymer Polymers 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 239000006260 foam Substances 0.000 abstract 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 2
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 229920003986 novolac Polymers 0.000 abstract 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002902 organometallic compounds Chemical class 0.000 abstract 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 2
- 229920005862 polyol Polymers 0.000 abstract 2
- 150000003077 polyols Chemical class 0.000 abstract 2
- 229920001451 polypropylene glycol Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- BXJWDOYMROEHEN-UHFFFAOYSA-N tributylstibane Chemical compound CCCC[Sb](CCCC)CCCC BXJWDOYMROEHEN-UHFFFAOYSA-N 0.000 abstract 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 abstract 1
- GSMSOLOCRKCJMR-UHFFFAOYSA-N 4-octadecylmorpholine Chemical class CCCCCCCCCCCCCCCCCCN1CCOCC1 GSMSOLOCRKCJMR-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 abstract 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 abstract 1
- RGAMPJYGTCSRAG-UHFFFAOYSA-N bis[2-(diethylamino)ethyl] hexanedioate Chemical compound CCN(CC)CCOC(=O)CCCCC(=O)OCCN(CC)CC RGAMPJYGTCSRAG-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 abstract 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 abstract 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 abstract 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000011496 polyurethane foam Substances 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- KKOFCVMVBJXDFP-UHFFFAOYSA-N triethylstibane Chemical compound CC[Sb](CC)CC KKOFCVMVBJXDFP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth 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
- C08G18/08—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
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A method for accelerating the reaction of an organic compound containing a reactive -NCY group in which Y is an oxygen or sulphur atom (such as a polyisocyanate or polyisothiocyanate) with a compound containing an active hydrogen atom (such as a polyester, polyether, polyesterether or polyesteramide) comprises reacting such compounds in the presence of a catalyst composition comprising a tertiary amine and an organic compound of the arsenic family, i.e. of arsenic, antimony or bismuth, such compound having at least one direct bond between carbon and an atom of arsenic, antimony or bismuth. The specified organic compounds of the arsenic family are those referred to in Specification 845,827. Tertiary amines specified are triethylamine, tributylamine, trioctylamine, N-methyl, ethyl and octadecylmorpholines, N-methyl or ethyldiethanolamine, N,N-dimethylethanolamine, N,N,N1,N1-tetramethylethylenediamine, N,N,N1,N1-tetramethyl-1,3-propanediamine, 1,-4-diazabicyclo[2.2.2]octane, N,N-dimethylbenzylamine, N,N-dimethyl- or diethylcyclohexylamine, benzyltriethylammonium bromide, bis(N,N-diethylaminoethyl)adipate, N-ethylhexamethyleneamine, N-ethylpiperidine, a -methylbenzyldimethylamine, dimethylhexadecylamine, 3-methylisoquinoline, dimethylcetylamine, and isocyanates and organometallic compounds containing tertiary nitrogen atoms; triethanolamine, triisopropanolamine, reaction products of alkylene oxides with triethanolamine, triisopropanolamine, ethylene diamine, ethanolamine and diethylenetriamine and polyesters derived from alkanolamines and/or polycarboxylic acids containing tertiary nitrogen. Suitable polyethers are listed, including straight polyoxyalkylene ethers, block copolymers of alkylene oxides and branched polyethers based on tri- and higher functional polyols, polyamines and aminoalcohols, urea-formaldehyde condensation products and novolaks. Starting materials for the polyesters and polyesteramides are also given. The polyisocyanates specified are substantially the same as those referred to in Specification 845,827. Examples describe the preparations of foams by the reaction of (1) polypropylene glycol, glycerol/propylene oxide reaction product, water, siloxane-oxyalkylene copolymer as emulsifier, 1,4-diaza-bicyclo-[2.2.2.]octane, and tributylarsine; (2) and (3) similar mixtures, replacing tributylarsine by tributylstibine and triethylstibine oxide, respectively.ALSO:A method for accelerating the reaction of an organic compound containing a reactive -NCY group in which Y is an oxygen or sulphur atom with a compound containing an active hydrogen atom comprises reacting such compounds in the presence of a catalyst composition comprising a tertiary amine and an organic compound having at least one direct bond between carbon and an atom of arsenic, antimony or bismuth. Specified for the latter compounds are those referred to in Specification 845,827. Lists of tertiary amines unreactive with isocyanate groups and those containing hydrogen atoms reactive with isocyanate groups are given. In an example phenyl isocyanate is reacted with butanol in the presence of triethyl stibine oxide and triethylamine, N,N,N1,N1-tetramethybutane diamine, and 1,4-diazabicyclo-[2.2.2] octane respectively.ALSO:A method of accelerating the reaction of an organic compound containing a reactive-NCY group in which Y is an oxygen or sulphur atom with a compound containing an active hydrogen atom (e.g. the reaction of a polyisocyanate or polyisothiocyanate with a polyester, polyether, polyester-ether or polyesteramide to give a polyurethane foam) comprises reacting such compounds in the preence of a catalyst composition comprising a tertiary amine and an organic compound of the arsenic family, such compound having at least one direct bond between carbon and an atom of arsenic, antimony or bismuth. The specified organic compounds of the arsenic family are those referred to in Specification 845,827. Tertiary amines (reactive and non-reactive with isocyanates) are listed, including as well as the more usual compounds also isocyanates and organo-metallic compounds containing tertiary nitrogen atoms, reaction products of alkylene oxides with alkanolamines, or polyamines, and polyesters derived from alkanolamines or polycarboxylic acids containing tertiary nitrogen. Suitable polyethers are listed, including straight polyoxyalkylene ethers, block copolymers of alkylene oxides and branched polyethers based on tri- and higher functional polyols, polyamines and amino-alcohols, urea formaldehyde condensation products and novolaks. Starting materials for the polyesters and polyesteramides are also given. The polyisocyanates specified are substantially the same as those referred to in Specification 845,827. Examples describe the preparation of foams by the reaction of (1) polypropylene glycol, glycerol/propylene oxide reaction product, water, siloxane-oxyalkylene copolymer as emulsifier, 1,4-diaza-bicyclo-[2.2.2.] octane, and tributylarsine; (2) and (3) similar mixtures in which the tributylarsine is replaced by tributylstibine and triethylstibine oxide, respectively.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US882547XA | 1958-12-08 | 1958-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882547A true GB882547A (en) | 1961-11-15 |
Family
ID=22210291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41186/59A Expired GB882547A (en) | 1958-12-08 | 1959-12-04 | Improvements in and relating to catalysts for isocyanate reactions |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1120131B (en) |
| FR (1) | FR1243115A (en) |
| GB (1) | GB882547A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140516A (en) * | 1977-05-31 | 1979-02-20 | Stauffer Chemical Company | Encapsulation process employing phase transfer catalysts |
| LU81024A1 (en) * | 1979-03-09 | 1980-09-24 | Prb Sa | PROCESS FOR THE PREPARATION OF FULL-SKIN POLYURETHANE AND POLYURETHANE OBTAINED |
| EP0427295A1 (en) * | 1985-05-28 | 1991-05-15 | The Dow Chemical Company | A process for preparing a polyurethane backed substrate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE958774C (en) * | 1953-08-22 | 1957-02-21 | Bayer Ag | Process for the production of foams based on polyurethane |
| DE1034850B (en) * | 1955-12-21 | 1958-07-24 | Bayer Ag | Accelerating the conversion of polyoxy compounds with polyisocyanates |
| BE548886A (en) * | 1956-06-22 | 1900-01-01 |
-
1959
- 1959-12-02 DE DEU6698A patent/DE1120131B/en active Pending
- 1959-12-04 GB GB41186/59A patent/GB882547A/en not_active Expired
- 1959-12-08 FR FR812452A patent/FR1243115A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1243115A (en) | 1960-10-07 |
| DE1120131B (en) | 1961-12-21 |
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