GB839185A - Improvements in or relating to the manufacture of cellular polymeric materials - Google Patents

Improvements in or relating to the manufacture of cellular polymeric materials

Info

Publication number
GB839185A
GB839185A GB34412/55A GB3441255A GB839185A GB 839185 A GB839185 A GB 839185A GB 34412/55 A GB34412/55 A GB 34412/55A GB 3441255 A GB3441255 A GB 3441255A GB 839185 A GB839185 A GB 839185A
Authority
GB
United Kingdom
Prior art keywords
acid
salts
diethylaminoethyl
salt
sulphonic
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
GB34412/55A
Inventor
Eric Arthur Packer
John Francis Wood
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
Priority to NL104983D priority Critical patent/NL104983C/xx
Priority to BE545745D priority patent/BE545745A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB34412/55A priority patent/GB839185A/en
Priority to DEI11365A priority patent/DE1056820B/en
Priority to FR1146869D priority patent/FR1146869A/en
Publication of GB839185A publication Critical patent/GB839185A/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
    • 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
    • C08G18/1875Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0008Foam properties flexible
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0025Foam properties rigid
    • 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
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent

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

Salts of tertiary amines with organic carboxylic or sulphonic acids may be made by mixing stoichiometric proportions of the ingredients in presence or absence of a solvent or diluent. Salts may be isolated as crystalline solids. Excess acid may be used and polybasic acids may yield the acid salts. The salts may be formed in a mixture of materials used for making polyurethanes. Amines mentioned are: triethylamine, N-ethylpiperidine, N : N - dimethylcyclohexylamine, triethanolamine, diethylaminoethanol, N - diethylaminoethyl benzamide, N - diethyl aminoethyl acetamide, di - (b - diethylaminoethyl) - adipate, the di - (b - diethylaminoethyl)-urethane of toluylene diisocyanate and pyridine. Acids mentioned are: oxalic, malonic, fumaric, maleic, glutaric, phthalic, isophthalic, terephthalic, formic, acetic, benzoic, salicylic, m- or p-hydroxybenzoic, hydroxy naphthoic, mono-, di- or tri-chloracetic, trifluoracetic, a -naphthalene sulphonic, citric, methacrylic and p-toluene sulphonic.ALSO:Cellular polymeric materials are made by the catalytic interaction of branched polyesters and organic polyisocyanates and, if desired, water (e.g. up to 10% by weight of the polyester), a salt of a tertiary amine with an organic carboxylic or sulphonic acid being used a catalyst. For making rigid cellular materials the catalyst is a salt of a sulphonic or a monocarboxylic acid. For resilient cellular materials, the polyester is one prepared from ingredients comprising 2-18 molar percentage based on the total dicarboxylic acid of at least one compound containing more than two isocyanate reactive groups, e.g. as described in Specification 790,420. Suitable tertiary amines are triethylamine, N - ethylpiperidine, N,N1 - dimethylcyclohexylamine, triethanolamine, diethylaminoethanol, N - diethylaminoethyl benzamide, N - diethylaminoethyl acetamide, di - (b -diethylaminoethyl) adipate, and the di-(b -diethylaminoethyl) urethane of toluylene diisocyanate and pyridine. Suitable organic acids for making the salts are oxalic, malonic, fumaric, maleic, glutaric, phthalic, isophthalic, terephthalic, formic, acetic, benzoic, salicyclic, m- or p-hydroxybenzoic, hydroxynaphthoic, monochloracetic, dichloracetic, trichloracetic, trifluoroacetic, a -naphthalene sulphonic, citric, methacrylic, and p-toluenesulphonic acids. The salts may be made by mixing the amine and acid in stoichiometric proportions in presence or absence of a solvent or diluent. The salt may be isolated or not before use. Excess acid may be used and in the case of a polyfunctional acid the salt may be an acid one. The salt may be formed by mixing the ingredients in situ in the reaction mixture. Conventional additives may be included, e.g. pigments, fillers, flame-proofing materials such as 2-chloroethyl phosphate, extenders such as tricresyl phosphate, ground polyester scrap, structure modifiers such as polyorganosiloxanes, and emulsifying agents such as soaps or ethylene oxide condensates. Blending of ingredients may be discontinuous or continuous as in Specification 839,183, and the ingredients may be mixed in any order. In a typical example (1) a liquid polymer from diethylene glycol, adipic acid and hexanetriol (OH value 46.1 mg. KOH/gram; acid value 5.1 mg. KOH/gram; viscosity 122 poises at 25 DEG C.) is mixed with a mixture of 2.4 and 2.6 toluylene diisocyanates. Water, an octyl phenol-ethylene oxide condensate and the monochloroacetate of diethylaminoethanol are added. A resilient cellular foam is obtained. The products may be formed into supported or unsupported sheets by spreading on to fabric or metal, e.g. with a doctor knife. Specifications 553,733, 760,782, 839,187, and German Specification 901,471 also are referred to.ALSO:In the production of cellular polyurethanes by reacting branched polyesters and polyisocyanates possibly in the presence of water, the catalyst used is a salt of a tertiary amine with an organic carboxylic of sulphic acid. The salt may be formed in situ in the reaction mixture. Sulphonic or monocarboxylic acid salts are used for rigid products. Specified polyesters are used for resilient products. The specifications lists a large number of suitable salts. Blending of ingredients may be in any order and may be discontinuous or continuous as in Specification 839,183. The products may be formed into supported or unsupported sheets by spreading on to fabric or metal.
GB34412/55A 1955-03-04 1955-03-04 Improvements in or relating to the manufacture of cellular polymeric materials Expired GB839185A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL104983D NL104983C (en) 1955-03-04
BE545745D BE545745A (en) 1955-03-04
GB34412/55A GB839185A (en) 1955-03-04 1955-03-04 Improvements in or relating to the manufacture of cellular polymeric materials
DEI11365A DE1056820B (en) 1955-03-04 1956-03-02 Process for the production of polyurethane foams
FR1146869D FR1146869A (en) 1955-03-04 1956-03-02 Manufacture of polymer materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB34412/55A GB839185A (en) 1955-03-04 1955-03-04 Improvements in or relating to the manufacture of cellular polymeric materials

Publications (1)

Publication Number Publication Date
GB839185A true GB839185A (en) 1960-06-29

Family

ID=10365314

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34412/55A Expired GB839185A (en) 1955-03-04 1955-03-04 Improvements in or relating to the manufacture of cellular polymeric materials

Country Status (5)

Country Link
BE (1) BE545745A (en)
DE (1) DE1056820B (en)
FR (1) FR1146869A (en)
GB (1) GB839185A (en)
NL (1) NL104983C (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4857560A (en) * 1986-03-08 1989-08-15 Bayer Aktiengesellschaft Reaction products useful as catalysts in the production of isocyanate-based plastics
GB2232990A (en) * 1989-05-19 1991-01-02 Bp Chem Int Ltd Process for preparing low density polyurethane foam
EP0656383B1 (en) * 1993-11-29 1999-03-10 OSi SPECIALTIES LTD. Improved process for preparing polyurethane foam
US6207725B1 (en) 1996-11-04 2001-03-27 Imperial Chemical Industries Plc Rigid polyurethane foams
US6403665B1 (en) 1996-11-04 2002-06-11 Imperial Chemical Industries Plc Rigid polyurethane foams
EP1622856A2 (en) * 2003-05-01 2006-02-08 Huntsman Petrochemical Corporation Heat activated tertiary amine urethane catalysts

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE589560A (en) * 1959-04-08
IL22629A (en) * 1963-12-23 1968-07-25 Allied Chem Method for making rigid cellular polyurethanes containing antimonates (iii)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE896413C (en) * 1944-01-18 1953-11-12 Bayer Ag Process for the production of high molecular weight plastics with the character of vulcanized rubber or leather
DE919072C (en) * 1944-06-13 1954-10-11 Dynamit Nobel Ag Process for accelerating the reaction of polyfunctional isocyanates or similar substances with compounds containing polyoxy or polycarboxyl groups
GB731071A (en) * 1951-07-19 1955-06-01 Du Pont Preparation of elastomers from polyalkylene ether glycols and diisocyanates
BE516512A (en) * 1951-12-24
DE926880C (en) * 1952-01-30 1955-04-25 Bayer Ag Process for the production of foams with a very low specific weight
DE950151C (en) * 1953-06-16 1956-10-04 Bayer Ag Process for accelerating the reaction of isocyanates with compounds containing hydroxyl groups in the production of foams
DE955993C (en) * 1953-08-19 1957-01-10 Bayer Ag Process for the production of, in particular, elastic foams from linear or branched polyesters and diisocyanates in the presence of water
DE962113C (en) * 1953-08-19 1957-04-18 Bayer Ag Process for the production of foams based on polyesters containing urethane groups

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4857560A (en) * 1986-03-08 1989-08-15 Bayer Aktiengesellschaft Reaction products useful as catalysts in the production of isocyanate-based plastics
GB2232990A (en) * 1989-05-19 1991-01-02 Bp Chem Int Ltd Process for preparing low density polyurethane foam
EP0656383B1 (en) * 1993-11-29 1999-03-10 OSi SPECIALTIES LTD. Improved process for preparing polyurethane foam
US6207725B1 (en) 1996-11-04 2001-03-27 Imperial Chemical Industries Plc Rigid polyurethane foams
US6346205B2 (en) 1996-11-04 2002-02-12 Huntsman International Llc Rigid polyurethane foams
US6403665B1 (en) 1996-11-04 2002-06-11 Imperial Chemical Industries Plc Rigid polyurethane foams
US6528549B2 (en) 1996-11-04 2003-03-04 Imperial Chemical Industries Plc Rigid polyurethane foams
EP1622856A2 (en) * 2003-05-01 2006-02-08 Huntsman Petrochemical Corporation Heat activated tertiary amine urethane catalysts
EP1622856A4 (en) * 2003-05-01 2008-08-27 Huntsman Spec Chem Corp Heat activated tertiary amine urethane catalysts
US7579426B2 (en) 2003-05-01 2009-08-25 Huntsman Petrochemical Corporation Heat activated tertiary amine urethane catalysts

Also Published As

Publication number Publication date
BE545745A (en)
DE1056820B (en) 1959-05-06
NL104983C (en)
FR1146869A (en) 1957-11-15

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