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GB773897A - Production of synthetic resinous condensation products and adhesives - Google Patents

Production of synthetic resinous condensation products and adhesives

Info

Publication number
GB773897A
GB773897A GB22903/54A GB2290354A GB773897A GB 773897 A GB773897 A GB 773897A GB 22903/54 A GB22903/54 A GB 22903/54A GB 2290354 A GB2290354 A GB 2290354A GB 773897 A GB773897 A GB 773897A
Authority
GB
United Kingdom
Prior art keywords
reaction
hydroxides
normal
ethyl
catalyst
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
GB22903/54A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical 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 Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB773897A publication Critical patent/GB773897A/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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

In making a resinous condensation product by reacting in the liquid state and under substantially anhydrous conditions an organic poly-isocyanate or -isothiocyanate with an organic compound containing a plurality of substituents containing active hydrogen atoms, an oxide, hydroxide, or alcoholate of an alkali metal or a quaternary ammonium base, as a catalyst, is present initially or is added during the course of the reaction. Long lists of reactants are given of which (a) cellulose, cellulose esters of acetic, propionic, butyric and nitric acids, cellulose mixed esters, methyl, ethyl, carboxylated and regenerated celluloses, and (b) polyvinyl alcohol acetate and propionate, polyvinyl acetal, polyvinyl ketals, polymers of acrylic, methacrylic and fumaric acids, and synthetic rubbers, e.g. neoprene and butadiene and substituted butadiene polymers and copolymers form two small groups exemplary of compounds containing active hydrogen. Catalysts specified are the oxides, hydroxides and alcoholates of sodium and potassium, benzyltrimethyl-, tetramethyl-, trimethylphenyl- and tetraethyl-ammonium hydroxides, and may be used in conjunction with tertiary amines, e.g. N-methyl- and N-ethyl-morpholines, triethyl-, tripropyl- and triamyl-amines, pyridine and quinoline. The catalyst is usually used in amount of 0.001 to 5 per cent by weight of the reactants. The reaction may be effected in the presence or absence of solvents, e.g. benzene, toluene, xylene, carbon tetrachloride, acetone, methylethylketone, ethyl acetate and amyl acetate, diluents or plasticisers, at normal, subor super-atmospheric pressures and at normal or elevated temperatures. In examples are given the curing rates of the condensation product of polyethylene glycol and tolylene diisocyanate (1) with different amounts of benzyltrimethylammonium hydroxide; (2) with different catalysts; and (3) with and without potassium hydroxide as catalyst. The products are useful in the production of films, fibres, textile finishing agents, bristles and coating or moulding compositions, bubble-free resins, resinous foams, potting resins, protective coatings, paints, varnishes, lacquers, laminates, vibration suppressors, radomes, abrasive articles, sound, heat and electrical insulators, condensers, insulating-rods and bushings, coil forms, coil mounting strips, safety glass, plastic articles, packaging materials and adhesives. Specification 486,878, [Group V], and U.S.A. Specifications 1,640,363, 1,915,808, 1,988,448 and 2,060,175 are referred to.ALSO:In making a condensation product by reacting in the liquid state and under substantially anhydrous conditions an organic poly-isocyanate or -isothiocyanate with a starch, dextrine or a protein or protein-like material, e.g. gelatine, casein, zein or leather, an oxide, hydroxide or alcoholate of an alkali metal or a quaternary ammonium base, as a catalyst, is present initially or is added during the course of the reaction. A long list of poly-isocyanates and -isothiocyanates is given. Catalysts specified are the oxides, hydroxides and alcoholates of sodium and potassium, benzyl-trimethyl-, tetramethyl -, trimethylphenyl - and tetraethyl - ammonium hydroxides, and may be used in conjunction with tertiary amines, e.g. N-methyl- and N-ethyl-morpholines, triethyl-, tripropyl- and triamyl-amines, pyridine and quinoline. The reaction may be effected in the presence or absence of solvents, e.g. benzene, toluene, xylene, carbon tetrachloride, acetone, methylethyl-ketone, ethyl acetate and amyl acetate, diluents or plasticisers, at normal, sub-or super-atmospheric pressures and at normal or elevated temperatures.ALSO:In making a resinous condensation product by reacting in the liquid state and under substantially anhydrous conditions an organic polyisocyanate or -isothiocyanate with natural rubber, balata, gutta percha, modified rubber or neoprene, an oxide, hydroxide or alcoholate of an alkali metal or a quaternary ammonium base, as a catalyst, is present initially or is added during the course of the reaction. A long list of isocyanates and isothiocyanates is given. Catalysts specified are the oxides, hydroxides and alcoholates of sodium and potassium, benzyltrimethyl-, tetramethyl-, trimethylphenyl- and tetraethylammonium hydroxides, and may be used in conjunction with tertiary amines, e.g. N-methyl- and N-ethyl-morpholines, triethyl-, tripropyl- and triamyl-amines, pyridine and quinoline. The reaction may be effected in the presence or absence of solvents, e.g. benzene, toluene, xylene, carbon tetrachloride, acetone, methylethylketone, ethyl acetate and amyl acetate, diluents or plasticizers, at normal sub- or superatmospheric pressures and at normal, or elevated temperatures.
GB22903/54A 1953-08-07 1954-08-06 Production of synthetic resinous condensation products and adhesives Expired GB773897A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US773897XA 1953-08-07 1953-08-07

Publications (1)

Publication Number Publication Date
GB773897A true GB773897A (en) 1957-05-01

Family

ID=22137769

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22903/54A Expired GB773897A (en) 1953-08-07 1954-08-06 Production of synthetic resinous condensation products and adhesives

Country Status (1)

Country Link
GB (1) GB773897A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3011984A (en) * 1957-06-14 1961-12-05 Exxon Research Engineering Co Oxonation of butyl rubber and covulcanization products of same with natural rubber or butadiene-styrene copolymer
US3040002A (en) * 1957-06-27 1962-06-19 Exxon Research Engineering Co Isocyanates
US3050489A (en) * 1958-03-26 1962-08-21 Exxon Research Engineering Co Method of stabilizing oxidized drying oils for isocyanate-sulphur dioxide curing
US3108100A (en) * 1957-06-12 1963-10-22 Ici Ltd Polymerization of organic isocyanates with organic hydroxides
US3207709A (en) * 1958-09-05 1965-09-21 Bayer Ag Preparation of cellular polyurethane plastics
US3346524A (en) * 1963-06-24 1967-10-10 Allied Chem Gloss retaining urethane coating composition
US3349049A (en) * 1963-09-30 1967-10-24 Emery Industries Inc Urethane coatings from hydroxyl terminated polyesters prepared from dimer acids

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3108100A (en) * 1957-06-12 1963-10-22 Ici Ltd Polymerization of organic isocyanates with organic hydroxides
US3011984A (en) * 1957-06-14 1961-12-05 Exxon Research Engineering Co Oxonation of butyl rubber and covulcanization products of same with natural rubber or butadiene-styrene copolymer
US3040002A (en) * 1957-06-27 1962-06-19 Exxon Research Engineering Co Isocyanates
US3112984A (en) * 1957-06-27 1963-12-03 Exxon Research Engineering Co Waterproofing agents and waterproofed materials
US3050489A (en) * 1958-03-26 1962-08-21 Exxon Research Engineering Co Method of stabilizing oxidized drying oils for isocyanate-sulphur dioxide curing
US3207709A (en) * 1958-09-05 1965-09-21 Bayer Ag Preparation of cellular polyurethane plastics
US3346524A (en) * 1963-06-24 1967-10-10 Allied Chem Gloss retaining urethane coating composition
US3349049A (en) * 1963-09-30 1967-10-24 Emery Industries Inc Urethane coatings from hydroxyl terminated polyesters prepared from dimer acids

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