GB896437A - Improvements in or relating to the manufacture of polymeric materials - Google Patents

Improvements in or relating to the manufacture of polymeric materials

Info

Publication number
GB896437A
GB896437A GB4057159A GB4057159A GB896437A GB 896437 A GB896437 A GB 896437A GB 4057159 A GB4057159 A GB 4057159A GB 4057159 A GB4057159 A GB 4057159A GB 896437 A GB896437 A GB 896437A
Authority
GB
United Kingdom
Prior art keywords
reaction
compounds
ended
water
polyethers
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
Application number
GB4057159A
Inventor
Francis George Jeffers
Derrick Michael O'mant
George Woods
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB4057159A priority Critical patent/GB896437A/en
Publication of GB896437A publication Critical patent/GB896437A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20Heterocyclic amines; Salts thereof
    • C08G18/2009Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2018Heterocyclic amines; Salts thereof containing one heterocyclic ring having one nitrogen atom in the ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/18Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20Heterocyclic amines; Salts thereof
    • C08G18/2081Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings

Abstract

A process for the manufacture of foamed polyurethane products by the interaction of secondary hydroxyl-ended polyethers and organic polyisocyanates or the isocyanate-ended reaction products of secondary hydroxyl-ended polyethers and organic polyisocyanates with water in the presence of a catalyst, is characterized in that the catalyst comprises an N-alkyl pyrrolidine. By an N-alkylpyrrolidine is meant a compound containing at least one pyrrolidine ring which carries an alkyl substituent on the nitrogen atom; the pyrrolidine ring and/or the alkyl group may carry other substituents. Suitable compounds are N-methyl, ethyl, propyl, butyl and octylpyrrolidines, 1:6-bis(pyrrolidino)hexane, 3:7-dimethyl 3:7-diaza bicyclo(3.3.0)octane and compounds of the general formula <FORM:0896437/IV (a)/1> where n is 0 or an integer from 1 to 6. As well as polymerization products of cyclic oxides there can also be used polyethers obtained by reaction of cyclic oxides with water, glycols, di- or polyethylene glycols, glyerol, triethanolamine, trimethylolpropane, pentaerythritol, sorbitol, sucrose, ethylene diamine, diethanolamine or dihydroxy stearic acid. The amount of polyisocyanate used is preferably such that after reaction with the end groups of the polyether, there is an excess of 3% to 5% by weight over the amount equivalent to the water used. The reaction may be modified by the incorporation of other ingredients and catalysts such as dimethylcyclohexylamine, N-methylmorpholine, potassium carbonate, potassium acetate, potassium naphthenate, manganous and manganic acetyl-acetonates, dialkyl tin compounds, ricinoleic acid, surface-active agents, silicone oil, ethyl cellulose, trimethylol propane, pigments, plasticizers such as dialkyl phthalates, tri-(b -chlorethyl) phosphate and antimony compounds.ALSO:A process for the manufacture of foamed polyurethane products by the interaction of secondary hydroxyl-ended polyethers and organic polyisocyanates or the isocyanate-ended reaction products of secondary hydroxyl-ended polyethers and organic polyisocyanates with water in the presence of a catalyst is characterized in that the catalyst comprises an N-alkyl pyrrolidine. By an N-alkyl-pyrrolidine is meant a compound containing at least one pyrrolidine ring which carries an alkyl substituent on the nitrogen atom; the pyrrolidine ring and/or the alkyl group may carry other substituents. Suitable compounds are N-methyl, ethyl, propyl, butyl and octylpyrrolidines, 1:6-bis (pyrrolidino)-hexane, 3:7-dimethyl 3:7-diaza bicyclo-(3.3.0) octane and compounds of the formula <FORM:0896437/V/1> where n is O or an integer from 1 to 6. As well as polymerization products of cyclic oxides there can also be used polyethers obtained by reaction of cyclic oxides with water, glycols, di- or polyethylene glycols, glycerol, triethanolamine, trimethylolpropane, pentaerythritol, sorbitol, sucrose, ethylene diamine diethanolamine or dihydroxy-stearic acid. The amount of polyisocyanate used is preferably such that after reaction with the end groups of the polyether, there is an excess of 3% to 5% by weight over the amount equivalent to the water used. The reaction may be modified by the incorporation of other ingredients and catalysts such as dimethylcyclohexylamine, N-methyl-morpholine, potassium carbonate, potassium naphthenate, managanous and manganic acetyl-acetonates, dialkyl tin compounds, ricinoleic acid surface-active agents, silicone oil, ethyl cellulose, trimethylol propane, pigments, plasticisers such as dialkyl phthalates, tri-(b -chlorethyl) phosphate and antimony compounds.
GB4057159A 1959-11-30 1959-11-30 Improvements in or relating to the manufacture of polymeric materials Expired GB896437A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4057159A GB896437A (en) 1959-11-30 1959-11-30 Improvements in or relating to the manufacture of polymeric materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4057159A GB896437A (en) 1959-11-30 1959-11-30 Improvements in or relating to the manufacture of polymeric materials

Publications (1)

Publication Number Publication Date
GB896437A true GB896437A (en) 1962-05-16

Family

ID=10415560

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4057159A Expired GB896437A (en) 1959-11-30 1959-11-30 Improvements in or relating to the manufacture of polymeric materials

Country Status (1)

Country Link
GB (1) GB896437A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0495249A1 (en) * 1991-01-12 1992-07-22 Bayer Ag Use of N-(aminoalkyl)-pyrrolidines as a catalyst for the polyisocyanate-poly-addition process, process for the preparation of polyurethane-ureas
WO2015200408A1 (en) 2014-06-27 2015-12-30 Huntsman Petrochemical Llc Pyrrolidine-based catalysts for use in polyurethane materials
WO2016020139A1 (en) * 2014-08-05 2016-02-11 Evonik Degussa Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
WO2016020138A1 (en) * 2014-08-05 2016-02-11 Evonik Degussa Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
EP3177659B1 (en) 2014-08-05 2020-12-09 Evonik Operations GmbH Nitrogen-containing compounds suitable for use in the production of polyurethanes
EP3999232A4 (en) * 2019-07-18 2023-06-07 Huntsman Petrochemical LLC Acid-blocked pyrrolidine catalysts for polyurethane foam

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0495249A1 (en) * 1991-01-12 1992-07-22 Bayer Ag Use of N-(aminoalkyl)-pyrrolidines as a catalyst for the polyisocyanate-poly-addition process, process for the preparation of polyurethane-ureas
WO2015200408A1 (en) 2014-06-27 2015-12-30 Huntsman Petrochemical Llc Pyrrolidine-based catalysts for use in polyurethane materials
CN106164117A (en) * 2014-06-27 2016-11-23 亨斯迈石油化学有限责任公司 Pyrrolidines catalyst for polyurethane material
EP3161029A4 (en) * 2014-06-27 2018-01-17 Huntsman Petrochemical LLC Pyrrolidine-based catalysts for use in polyurethane materials
US9988483B2 (en) 2014-06-27 2018-06-05 Huntsman Petrochemical Llc Pyrrolidine-based catalysts for use in polyurethane materials
CN106164117B (en) * 2014-06-27 2020-01-17 亨斯迈石油化学有限责任公司 Pyrrolidine catalysts for polyurethane materials
WO2016020139A1 (en) * 2014-08-05 2016-02-11 Evonik Degussa Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
WO2016020138A1 (en) * 2014-08-05 2016-02-11 Evonik Degussa Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
US10457769B2 (en) 2014-08-05 2019-10-29 Evonik Degussa Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
US10703851B2 (en) 2014-08-05 2020-07-07 Evonik Operations Gmbh Nitrogen-containing compounds suitable for use in the production of polyurethanes
EP3177659B1 (en) 2014-08-05 2020-12-09 Evonik Operations GmbH Nitrogen-containing compounds suitable for use in the production of polyurethanes
EP3999232A4 (en) * 2019-07-18 2023-06-07 Huntsman Petrochemical LLC Acid-blocked pyrrolidine catalysts for polyurethane foam

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