GB783615A - Diisocyanate-modified polyesters and rubber-like materials derived therefrom - Google Patents

Diisocyanate-modified polyesters and rubber-like materials derived therefrom

Info

Publication number
GB783615A
GB783615A GB2470554A GB2470554A GB783615A GB 783615 A GB783615 A GB 783615A GB 2470554 A GB2470554 A GB 2470554A GB 2470554 A GB2470554 A GB 2470554A GB 783615 A GB783615 A GB 783615A
Authority
GB
United Kingdom
Prior art keywords
diisocyanate
water
acid
cross
rubber
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
GB2470554A
Inventor
Laurence Stephen Rayn Er
Mervyn Frederick Vincent
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 BE540800D priority Critical patent/BE540800A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2470554A priority patent/GB783615A/en
Priority to FR1141434D priority patent/FR1141434A/en
Publication of GB783615A publication Critical patent/GB783615A/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
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • 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
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/22Catalysts containing metal compounds
    • C08G18/225Catalysts containing metal compounds of alkali or alkaline earth metals

Abstract

A material convertible into a rubber is made by reacting a molar excess of a diisocyanate with a polyethylene glutarate of molecular weight at least 1000 and preferably 3000 to 7000. Reaction may be effected in two stages in the first of which less than an equivalent amount of diisocyanate is used and in the second of which additional diisocyanate is dispersed in the composition. A small amount of water may be present during the reaction and the reaction may be moderated by adding acidic materials, e.g. sulphur dioxide, boric acid, adipic acid, salicylic acid or butadiene sulphone (which decomposes into butadiene and sulphur dioxide). The diisocyanate modified polyester may be converted into a rubber (a) by heating it with a basic catalyst, e.g. lithium, sodium, potassium, beryllium, magnesium, calcium or barium hydroxide; sodium methoxide or ethoxide; or pyridine, trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, tribenzylamine or dimethylaniline and/or (b) by heating with a cross-linking agent, e.g. water, glycerol, triethanolamine, ethylene glycol, 1 : 3-propane diol, 1 : 4-butane diol, ethylene diamine, trimethylene diamine, tetramethylene diamine, m-phenylene diamine, o- or m-dichlorobenzidine, dianisidine, 4,41-diamino-diphenyl methane, naphthylene diamines, tolylene 2,4-diamine, p-aminobenzyl aniline, o- or p-aminodiphenyl-amine, 2-amino ethyl alcohol, 2-amino1 - naphthol, m - aminophenol, glycollic acid, alpha-hydroxy propionic acid, amino acetic acid and amino benzoic acid. When water is used as cross-linking agent it may be added in the form of a salt containing water of crystallization, e.g. cobaltous chloride hexahydrate or the diisocyanate modified polyester may be made to take up water by heating it in an oven having an atmosphere of low humidity or by exposing it to the atmosphere. After adding the catalyst or cross-linking agent the composition may be converted into chips, ribbons, films, sheets, fibres, filaments, solutions or dispersions. When the composition is fluid and a cross-linking agent giving rise to evolution of a gas is used (e.g. water or steam), an expanded material may be obtained by heating in a suitable mould. The cross-linking reaction may be controlled by methods described in Specifications 767,017 and 773,991. Carbon black may be added to the reactants during the preparation of the rubber.
GB2470554A 1954-08-25 1954-08-25 Diisocyanate-modified polyesters and rubber-like materials derived therefrom Expired GB783615A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE540800D BE540800A (en) 1954-08-25
GB2470554A GB783615A (en) 1954-08-25 1954-08-25 Diisocyanate-modified polyesters and rubber-like materials derived therefrom
FR1141434D FR1141434A (en) 1954-08-25 1955-08-10 New artificial resins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2470554A GB783615A (en) 1954-08-25 1954-08-25 Diisocyanate-modified polyesters and rubber-like materials derived therefrom

Publications (1)

Publication Number Publication Date
GB783615A true GB783615A (en) 1957-09-25

Family

ID=10215955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2470554A Expired GB783615A (en) 1954-08-25 1954-08-25 Diisocyanate-modified polyesters and rubber-like materials derived therefrom

Country Status (3)

Country Link
BE (1) BE540800A (en)
FR (1) FR1141434A (en)
GB (1) GB783615A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3107235A (en) * 1958-04-07 1963-10-15 Goodyear Tire & Rubber Composition comprising a polyester, dichlorobenzidine and 3, 3'-dimethyl-4, 4'-diphenylene dhsocyanate and tire made therefrom
US3192185A (en) * 1959-05-19 1965-06-29 Eagle Picher Co Homogenized crosslinked polyurethanes
US3218215A (en) * 1960-04-27 1965-11-16 Eagle Picher Co Adhering polyurethane to metal
US3259516A (en) * 1960-05-25 1966-07-05 Thiokol Chemical Corp Method of thermally insulating articles with a filled polyurethane composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3107235A (en) * 1958-04-07 1963-10-15 Goodyear Tire & Rubber Composition comprising a polyester, dichlorobenzidine and 3, 3'-dimethyl-4, 4'-diphenylene dhsocyanate and tire made therefrom
US3192185A (en) * 1959-05-19 1965-06-29 Eagle Picher Co Homogenized crosslinked polyurethanes
US3218215A (en) * 1960-04-27 1965-11-16 Eagle Picher Co Adhering polyurethane to metal
US3259516A (en) * 1960-05-25 1966-07-05 Thiokol Chemical Corp Method of thermally insulating articles with a filled polyurethane composition

Also Published As

Publication number Publication date
BE540800A (en)
FR1141434A (en) 1957-09-02

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