GB871291A - Production of hydrophilic polyester-urethane foamed or cellular products - Google Patents

Production of hydrophilic polyester-urethane foamed or cellular products

Info

Publication number
GB871291A
GB871291A GB760/58A GB76058A GB871291A GB 871291 A GB871291 A GB 871291A GB 760/58 A GB760/58 A GB 760/58A GB 76058 A GB76058 A GB 76058A GB 871291 A GB871291 A GB 871291A
Authority
GB
United Kingdom
Prior art keywords
polyester
acids
bisulphite
polyol
reacted
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
GB760/58A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB871291A publication Critical patent/GB871291A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/36After-treatment
    • C08J9/40Impregnation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
    • C08J2375/06Polyurethanes from polyesters

Abstract

A method of imparting hydrophilicity to a polyester-polyurethane foam by introducing therein sulphonate and/or sulphonic acid groups comprises treating a foamed polyester-polyurethane mass with an aqueous solution of an alkali metal sulphite or bisulphite at a temperature from room temperature to 100 DEG C., said foamed mass being formed by the reaction, in the presence of water or a compound that releases water, of (a) one or more polyisocyanates and (b) one or more polyester resins each obtained from a mixture comprising a polyol component and a dicarboxylic acid component, at least 10 mole per cent of the dicarboxylate groups in the polyester resin or mixture of resins being derived from one or more alphabeta ethylenically unsaturated aliphatic dicarboxylic acids, anhydrides or esters. The polyester may be derived from such unsaturated acids as maleic, citraconic, mesaconic, fumaric and itaconic, and it may be mixed with a polyester obtained from saturated reactants. Alternatively, a combination polyester form mixed saturated and unsaturated acids can be used. The polyol may be a diol, such as ethylene, diethylene, propylene, dipropylene or trimethylene glycols, or 1, 3- or 1, 4-butane-diol or 1, 5-pentanediol. Higher polyols include glycerol, sorbitol, pentaerythritol, inositol, tetramethylcyclohexanol, di- and poly-pentaerythritol and trimethylolpropane. The polyol and dicarboxylic acids are reacted in the molar ratio 1,2 to 1,8 : 1. Sulphuri or toluene sulphonic acids, zinc chloride and phosphorous pentoxide are suitable esterification catalysts. The polyester may be modified with a fatty acid having 8-30 carbon atoms, such as lauric, stearic, oleic, linoleic, linolenic, palmitic or ricinoleic acids, by reaction directly or as its glycerol ester with the polyol or hydroxypolyester. Preferably the modifier is reacted with the polyol before the reaction with the dicarboxylic acid. Hydrophilic fillers such as cotton and regenerated cellulose rayon fibres and filaments may be incorporated in the products. The treatment of the polyurethane foam with the alkali metal sulphite or bisulphite is preferably effected at a pH of 5,5-13. A metabisulphite may be used if caustic soda or potash is added to convert it to a simple bisulphite. The solution may be entirely aqueous or may contain, for example, isopropanol, ethanol, butanol, acetone, methyl ethyl ketone, dimethylformamide or glycol. Wetting agents may also be present. In Examples (1) a polyester prepared from adipic, maleic and capric acids and glycerol is reacted with N-alkylmorpholine, water silicone fluid and 2, 4- and 2, 6-toluene diisocyanates to give a polyurethane foam. This is treated with saturated sodium bisulphite solution at 60 DEG C.; (2) a polyester from adipic acid, maleic anhydride, diethylene glycol and trimethylolmethane is reacted similarly; (3) in a process similar to (2) the bisulphite treatment is preceded by immersion of the foam in isopropanol to cause swelling; (4) a mixture of water, sodium metabisulphite, sodium hydroxide and isopropanol is used in the final treatment; (5) the final step is effected at 100 DEG C.ALSO:A method of imparting hydrophilicity to a polyester-polyurethane foam by introducing therein sulphonate and/or sulphonic acid groups comprises treating a foamed polyester-polyurethane mass with an aqueous solution of an alkali metal sulphite or bisulphite at a temperature from room temperature to 100 DEG C., said foamed mass being formed by the reaction, in the presence of water or a compound that releases water, of (a) one or more polyisocyanates and (b) one or more polyester resins each obtained from a mixture comprising a polyol component and a dicarboxylic acid component, at least 10 mole per cent. of the dicarboxylate groups in the polyester resin or mixture of resins being derived from one or more alphabeta ethylenically unsaturated aliphatic dicarboxylic acids, anhydrides or esters. The polyester may be derived from such unsaturated acids as maleic, citraconic, mesaconic, fumaric and itaconic, and it may be mixed with a polyester obtained from saturated reactants. Alternatively, a combination polyester form mixed saturated and unsaturated acids can be used. The polyol may be a diol, such as ethylene, diethylene, propylene, dipropylene or trimethylene glycols, or 1, 3- or 1, 4-butane-diol or 1, 5-pentanediol. Higher polyols include glycerol, sorbitol, pentaerythritol, inositol, tetramethylcyclohexanol, di- and poly-pentaerythritol and trimethylolpropane. The polyol and dicarboxylic acids are reacted in the molar ratio 1,2 to 1,8 : 1. Sulphuric or toluene sulphonic acids, zinc chloride and phosphorus pentoxide are suitable esterification catalysts. The polyester may be modified with a fatty acid having 8 to 30 carbon atoms, such as lauric, sterric, oleic, linoloic, linolenic, palmitic or ricinoleic acids, by reaction directly or as its glycerol ester with the polyol or hydroxy-polyester. Preferably the modifier is reacted with the polypol before the reaction with the dicarboxylic acid. Hydrophilic fillers such as cotton and regenerated cellulose rayon fibres and filaments may be incorporated in the products. The treatment of the polyurethane foam with the alkali metal sulphite or bisulphite is preferably effected at a pH of 5,5 to 13. A metabisulphite may be used if caustic soda or potash is added to convert it to a simple bisulphite. The solution may be entirely aqueous or may contain, for example, isopropanol, ethanol, butanol, acetone, methyl ethyl ketone, dimethylformamide or glycol. Wetting agents may also be present. In Examples (1) a polyester prepared from adipic, maleic and capric acids and glycorol is reacted with N-alkylmorpholine, water silicone fluid and 2, 4- and 2, 6- toluene diisocyanates to give a polyurethane foam. This is treated with saturated sodium bisulphite solution at 60 DEG C.; (2) a polyester from adipic acid, maleic anhydride, diethylene glycol and trimethylolmethane is reacted similarly; (3) in a process similar to (2) the bisulphite treatment is preceded by immersion of the foam in isopropanol to cause swelling; (4) a mixture of water, sodium metabisulphite, sodium hydroxide and isopropanol is used in the final treatment; (5) the final step is effected at 100 DEG C.
GB760/58A 1957-01-14 1958-01-08 Production of hydrophilic polyester-urethane foamed or cellular products Expired GB871291A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US871291XA 1957-01-14 1957-01-14

Publications (1)

Publication Number Publication Date
GB871291A true GB871291A (en) 1961-06-28

Family

ID=22203288

Family Applications (1)

Application Number Title Priority Date Filing Date
GB760/58A Expired GB871291A (en) 1957-01-14 1958-01-08 Production of hydrophilic polyester-urethane foamed or cellular products

Country Status (1)

Country Link
GB (1) GB871291A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130237624A1 (en) * 2010-11-22 2013-09-12 Bayer Intellectual Property Gmbh Method for producing flexible polyurethane foams
US8906497B2 (en) 2009-01-22 2014-12-09 Eurofoam Gmbh Foam element with hydrophilic substances incorporated in it
WO2016061068A1 (en) 2014-10-13 2016-04-21 Air Products And Chemicals, Inc. Polyurethane catalysts from sulfur based salts
CN114853996A (en) * 2022-05-18 2022-08-05 中南民族大学 High-temperature-resistant hyperbranched polyester, preparation method, application and nylon composite material
CN115368538A (en) * 2022-09-16 2022-11-22 四川亭江新材料股份有限公司 Polyurethane type leather fatting agent and preparation method thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8906497B2 (en) 2009-01-22 2014-12-09 Eurofoam Gmbh Foam element with hydrophilic substances incorporated in it
US20130237624A1 (en) * 2010-11-22 2013-09-12 Bayer Intellectual Property Gmbh Method for producing flexible polyurethane foams
WO2016061068A1 (en) 2014-10-13 2016-04-21 Air Products And Chemicals, Inc. Polyurethane catalysts from sulfur based salts
WO2017065832A1 (en) 2014-10-13 2017-04-20 Air Products And Chemicals, Inc. Polyurethane catalysts from sulfur based salts
US10472459B2 (en) 2014-10-13 2019-11-12 Evonik Degussa Gmbh Polyurethane catalysts from a sulfur based salts
US10570245B2 (en) 2014-10-13 2020-02-25 Evonik Operations Gmbh Polyurethane catalysts from sulfur based salts
CN114853996A (en) * 2022-05-18 2022-08-05 中南民族大学 High-temperature-resistant hyperbranched polyester, preparation method, application and nylon composite material
CN114853996B (en) * 2022-05-18 2024-02-02 中南民族大学 High-temperature-resistant hyperbranched polyester, preparation method, application and nylon composite material
CN115368538A (en) * 2022-09-16 2022-11-22 四川亭江新材料股份有限公司 Polyurethane type leather fatting agent and preparation method thereof
CN115368538B (en) * 2022-09-16 2023-12-26 四川亭江新材料股份有限公司 Polyurethane leather fatting agent and preparation method thereof

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