GB891007A - Improvements in or relating to the manufacture of foamed polymeric materials - Google Patents

Improvements in or relating to the manufacture of foamed polymeric materials

Info

Publication number
GB891007A
GB891007A GB14017/59A GB1401759A GB891007A GB 891007 A GB891007 A GB 891007A GB 14017/59 A GB14017/59 A GB 14017/59A GB 1401759 A GB1401759 A GB 1401759A GB 891007 A GB891007 A GB 891007A
Authority
GB
United Kingdom
Prior art keywords
polyisocyanate
diphenylmethane diisocyanate
weight
composition
diethylaminoethyl
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
GB14017/59A
Inventor
Arthur Lowe
Joseph Simons
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 GB14017/59A priority Critical patent/GB891007A/en
Publication of GB891007A publication Critical patent/GB891007A/en
Expired legal-status Critical Current

Links

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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
    • C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
    • C08G18/425—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids the polyols containing one or two ether groups
    • 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
    • C08G18/089—Reaction retarding agents
    • 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
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • 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
    • C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/0058—≥50 and <150kg/m3
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/60—Compositions for foaming; Foamed or intumescent adhesives

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 there are used (a) a polyisocyanate composition containing sufficient carbamylchloride derivatives to provide an ionizable chlorine content of between 0,1% and 0,25% by weight, at least 5% by weight of a polyisocyanate containing more than two isocyanate groups and a major proportion of diphenylmethane diisocyanate, the isocyanate content of the composition being between 85% and 95% calculated as diphenylmethane diisocyanate, (b) a linear or slightly branched polyester, and (c) a catalyst consisting of an alkali metal hydroxide or an alkali metal salt of a weak acid. The carbamyl chloride derivatives of the polyisocyanate composition comprise the diisocyanate and trisocyanate compounds of the composition wherein some or all of the isocyanate groups have been converted to N-substituted carbamyl chloride groups, for example by direct addition of hydrogen chloride. The preferred polyesters are of the kind described in Specification 790,420. In addition to the catalyst (c) there is advantageously used a tertiary amine such as triethylamine, di(diethylaminoethyl)-adipate, diethylaminoethyl carbanilate, diethylaminopropionamide, diethylaminoethyl benzyl ether, N-methyl morpholine, N-ethyl-piperidine, dimethylcyclohexylamine, N-ethylhexamethyleneimine, triethylene diamine and N,N,N1, N1-tetramethylhexamethylene diamine. The reaction mixture may also contain surface-active agents, fillers such as carbon black, silica, mica, French chalk, starch, colouring matters, flame-proofing agents, e.g. tri-chlorethyl phosphate and additional gas forming materials such as fluorinated alkanes. The mixture of reactants can be put into moulds or on to substrates such as woven or unwoven textiles, linoleum, plastic films such as polyvinyl chloride, copolymers of styrene, butadiene and acrylonitrile, piping, and tufted carpets, where foaming takes place. In Examples (1) a cellular product is obtained by reacting a diethylene glycol/pentaerythritol/adipic acid polyester, aqueous sodium carbonate solution and a polyisocyanate composition with a strenght of 87,5% calculated as diphenylmethane diisocyanate and an ionizable chlorine content of 0,12%, obtained by phosgenating a crude diaminodiphenyl methane containing about 15% by weight of polyamines, mainly triamines; (7) in a similar process trichlorofluoromethane is dissolved in the polyisocyanate before it is added to the reaction mixture. Uses. Carpet backing, coated plastic films, packaging, facia panels, seats, arm-rests.ALSO:In an improvement or modification of the process of the parent Specification there are used (a) a polyisocyanate composition containing sufficient carbamyl chloride derivatives to provide an ionisable chlorine content of between 0,1% and 0,25% by weight, at least 5% by weight of a polyisocyanate containing more than two isocyanate groups and a major proportion of diphenylmethane diisocyanate, the isocyanate content of the composition being between 85% and 95% calculated as diphenylmethane diisocyanate, (b) a linear or slightly branched polyester, and (c) a catalyst consisting of an alkali metal hydroxide or an alkali metal salt of a weak acid. The carbamyl chloride derivatives of the polyisocyanate composition comprise the diisocyanate and triisocyanate compounds of the composition wherein some or all of the isocyanate groups have been convered to N-substituted carbamyl chloride groups, for example by direct addition of hydrogen chloride. The preferred polyesters are of the kind described in Specification 790,420. In addition to the catalyst (c) there is advantageously used a tertiary amine such as triethylamine, di(diethylamino-ethyl)-adipate, diethylaminoethyl carbanilate, di-ethylaminopropionamide, diethylaminoethyl benzyl ether, N-methyl morpholine, N-ethyl-piperidine, dimethylcyclohexylamine, N-ethyl-hexamethyleneimine, triethylene diamine and N,N,N1,N1-tetramethyl-hexamethylene diamine. The reaction mixture may also contain surface active agents, fillers such as carbon black, silica, mica, French chalk, starch, colouring matters, flameproofing agents, e.g., tri-chlorethyl phosphate and additional gas forming materials such as fluorinated alkanes. The mixture of reactants can be put into moulds or on to substrates such as woven or unwoven textiles, linoleum, plastic films such as polyvinyl chloride, copolymers of styrene, butadiene and acrylonitrile, piping and tufted carpets, where foaming takes place. In Examples (1) a cellular product is obtained by reacting a diethylene glycol/pentaerythritol/adipic acid polyester, aqueous sodium carbonate solution and a polyisocyanate composition with a strength of 87,5% calculated as diphenylmethane diisocyanate and an ionisable chlorine content of 0,12%, obtained by phosgenating a crude diaminodiphenyl methane containing about 15% by weight of polyamines, mainly triamines; (7) in a similar process trichlorofluoromethane is dissolved in the polyisocyanate before it is added to the reaction mixture.
GB14017/59A 1959-04-24 1959-04-24 Improvements in or relating to the manufacture of foamed polymeric materials Expired GB891007A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB14017/59A GB891007A (en) 1959-04-24 1959-04-24 Improvements in or relating to the manufacture of foamed polymeric materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB14017/59A GB891007A (en) 1959-04-24 1959-04-24 Improvements in or relating to the manufacture of foamed polymeric materials

Publications (1)

Publication Number Publication Date
GB891007A true GB891007A (en) 1962-03-07

Family

ID=10033476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14017/59A Expired GB891007A (en) 1959-04-24 1959-04-24 Improvements in or relating to the manufacture of foamed polymeric materials

Country Status (1)

Country Link
GB (1) GB891007A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3620985A (en) * 1968-09-16 1971-11-16 M & T Chemicals Inc Urethane foam catalyst and process for preparing urethane foam
US4009130A (en) * 1975-06-11 1977-02-22 Texaco Development Corporation Preparation of isocyanurate foams using alkali metal tertiaryamino dithiocarbamate salt catalysts
US4067832A (en) 1976-03-01 1978-01-10 The Procter & Gamble Company Flexible polyurethane foam
US4107069A (en) * 1975-07-02 1978-08-15 M&T Chemicals Inc. Storage-stable precursors for rigid polyurethane foams
US4150206A (en) 1976-03-12 1979-04-17 S.A. Prb Process for preparing polyurethane with integral skin
US4242463A (en) 1979-12-19 1980-12-30 Sheller-Globe Corporation Color stable integral skin foam
CN112225859A (en) * 2020-09-29 2021-01-15 苏州思德新材料科技有限公司 Catalyst for polyurethane foam production and preparation method thereof
US11414160B2 (en) 2017-11-20 2022-08-16 Svitzer A/S Tugboat

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3620985A (en) * 1968-09-16 1971-11-16 M & T Chemicals Inc Urethane foam catalyst and process for preparing urethane foam
US4009130A (en) * 1975-06-11 1977-02-22 Texaco Development Corporation Preparation of isocyanurate foams using alkali metal tertiaryamino dithiocarbamate salt catalysts
US4107069A (en) * 1975-07-02 1978-08-15 M&T Chemicals Inc. Storage-stable precursors for rigid polyurethane foams
US4067832A (en) 1976-03-01 1978-01-10 The Procter & Gamble Company Flexible polyurethane foam
US4150206A (en) 1976-03-12 1979-04-17 S.A. Prb Process for preparing polyurethane with integral skin
US4242463A (en) 1979-12-19 1980-12-30 Sheller-Globe Corporation Color stable integral skin foam
DE3022093A1 (en) * 1979-12-19 1981-07-02 Sheller-Globe Corp., Toledo, Ohio COLOR-RESISTANT INTEGRAL SKIN FOAM
US11414160B2 (en) 2017-11-20 2022-08-16 Svitzer A/S Tugboat
US11702173B2 (en) 2017-11-20 2023-07-18 Svitzer A/S Tugboat
CN112225859A (en) * 2020-09-29 2021-01-15 苏州思德新材料科技有限公司 Catalyst for polyurethane foam production and preparation method thereof

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