GB839185A - Improvements in or relating to the manufacture of cellular polymeric materials - Google Patents
Improvements in or relating to the manufacture of cellular polymeric materialsInfo
- 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
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
- C08G18/08—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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
-
- 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
- C08G2110/0025—Foam properties rigid
-
- 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
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.
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)
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)
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)
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 |
-
0
- NL NL104983D patent/NL104983C/xx active
- BE BE545745D patent/BE545745A/xx unknown
-
1955
- 1955-03-04 GB GB34412/55A patent/GB839185A/en not_active Expired
-
1956
- 1956-03-02 FR FR1146869D patent/FR1146869A/en not_active Expired
- 1956-03-02 DE DEI11365A patent/DE1056820B/en active Pending
Cited By (10)
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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