GB840097A - Production of high molecular weight polyurethane plastics - Google Patents
Production of high molecular weight polyurethane plasticsInfo
- Publication number
- GB840097A GB840097A GB831658A GB831658A GB840097A GB 840097 A GB840097 A GB 840097A GB 831658 A GB831658 A GB 831658A GB 831658 A GB831658 A GB 831658A GB 840097 A GB840097 A GB 840097A
- Authority
- GB
- United Kingdom
- Prior art keywords
- castor oil
- polyhydroxy compound
- reacted
- oleic
- ester
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 229920003023 plastic Polymers 0.000 title 1
- 239000004033 plastic Substances 0.000 title 1
- 229920002635 polyurethane Polymers 0.000 title 1
- 239000004814 polyurethane Substances 0.000 title 1
- 239000004359 castor oil Substances 0.000 abstract 10
- 235000019438 castor oil Nutrition 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 10
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 6
- 235000021313 oleic acid Nutrition 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- -1 fatty acid ester Chemical class 0.000 abstract 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 4
- 235000021314 Palmitic acid Nutrition 0.000 abstract 3
- 235000021355 Stearic acid Nutrition 0.000 abstract 3
- 150000002943 palmitic acids Chemical class 0.000 abstract 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005642 Oleic acid Substances 0.000 abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000006260 foam Substances 0.000 abstract 2
- 150000002334 glycols Chemical class 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 229940049964 oleate Drugs 0.000 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 2
- 229920001228 polyisocyanate Polymers 0.000 abstract 2
- 239000005056 polyisocyanate Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- DHTGRDDBCWWKQJ-UHFFFAOYSA-N 2-(2,2-dihydroxyethoxy)ethane-1,1-diol Chemical compound OC(O)COCC(O)O DHTGRDDBCWWKQJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 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
- C08G18/56—Polyacetals
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)
Abstract
In an improvement or modification of the process of the parent Specification a fatty acid ester containing at least two hydroxyl groups in the molecule is incorporated into or mixed with the polyhydroxy compound specified in the parent Specification. The ester may be mixed with the polyhydroxy compound or may be incorporated into the polyhydroxy compound during its manufacture by inclusion with the reactants used to form the polyhydroxy compound. Alternatively the ester and the polyhydroxy compound may be linked by reaction with a diisocyanate to give a material still containing OH groups, which is then reacted with polyisocyanate. Specified fatty acid esters are castor oil, hydrogenated castor oil, ricinoleic glycol esters, ricinoleic - 5,18 - octadecenediol monoesters, reaction products of castor oil, oleic acid, phthalic acid and glycol, monoglycerides of oleic, stearic, and palmitic acids, the OH groups of which have been reacted with ethylene oxide, and hydroxyethylated monoesters of oleic, stearic and palmitic acids with trimethylol propane or pentaerythritol. In a typical example, (1) a hydroxy compound obtained by condensing 1,4-butane-b -dihydroxyethyl ether, castor oil and paraformaldehyde in the presence of p-toluene sulphonic acid is reacted with toluylene diisocyanate and water in the presence of ethyl g -dimethylaminopropyl ether, diethyl ammonium oleate and aqueous sulphonated castor oil, to give a foam.ALSO:In an improvement or modification of the process of the parent Specification a fatty acid ester containing at least two hydroxyl groups in the molecule is incorporated into or mixed with the polyhydroxy compound specified in the parent Specification. The ester may be mixed with the polyhydroxy compound or may be incorporated into the polyhydroxy compound during its manufacture by inclusion with the reactants used to form the polyhydroxy compound. Alternatively the ester and the polyhydroxy compound may be linked by reaction with a diisocyanate to give a material still containing OH groups, which is then reacted with polyisocyanate. Specified fatty acid esters are castor oil, hydrogenated castor oil, ricinoleic glycol esters, ricinoleic-5, 18-octadecenediol monoesters, reaction products of castor oil, oleic acid, phthalic acid and glycol, monoglycerides of oleic, stearic and pamiltic acids, the OH groups of which have been reacted with ethylene oxide, and hydroxyethylated monoesters of oleic, stearic and palmitic acids with trimethylol propane or pentaerythritol. In a typical example (1) a hydroxy compound obtained by condensing 1, 4-butane-b dihydroxyethyl ether, castor oil and paraformaldehyde in the presence of p-toluene sulphonic acid is reacted with toluylene diisocyanate and water in the presence of ethyl g -dimethylaminopropyl ether, diethyl ammonium oleate and aqueous sulphonated castor oil, to give a foam.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22619A DE1045095B (en) | 1957-03-19 | 1957-03-19 | Process for the production of high molecular weight plastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB840097A true GB840097A (en) | 1960-07-06 |
Family
ID=7090512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB831658A Expired GB840097A (en) | 1957-03-19 | 1958-03-14 | Production of high molecular weight polyurethane plastics |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1045095B (en) |
| FR (1) | FR1165085A (en) |
| GB (1) | GB840097A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006118995A1 (en) * | 2005-04-29 | 2006-11-09 | Dow Global Technologies, Inc. | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131002B (en) * | 1960-10-13 | 1962-06-07 | Bayer Ag | Process for the production of foams containing urethane groups |
-
1956
- 1956-10-24 FR FR1165085D patent/FR1165085A/en not_active Expired
-
1957
- 1957-03-19 DE DEF22619A patent/DE1045095B/en active Pending
-
1958
- 1958-03-14 GB GB831658A patent/GB840097A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006118995A1 (en) * | 2005-04-29 | 2006-11-09 | Dow Global Technologies, Inc. | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
| US7750108B2 (en) | 2005-04-29 | 2010-07-06 | Dow Global Technologies Inc. | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1045095B (en) | 1958-11-27 |
| FR1165085A (en) | 1958-10-17 |
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