GB1023295A - Process for the preparation of curable compositions of alkenyl resins - Google Patents

Process for the preparation of curable compositions of alkenyl resins

Info

Publication number
GB1023295A
GB1023295A GB984064A GB984064A GB1023295A GB 1023295 A GB1023295 A GB 1023295A GB 984064 A GB984064 A GB 984064A GB 984064 A GB984064 A GB 984064A GB 1023295 A GB1023295 A GB 1023295A
Authority
GB
United Kingdom
Prior art keywords
copolymer
esters
acids
branched acids
vinyl esters
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
GB984064A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB1023295A publication Critical patent/GB1023295A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
    • C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C08L31/04—Homopolymers or copolymers of vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F18/02—Esters of monocarboxylic acids
    • C08F18/04—Vinyl esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F18/02—Esters of monocarboxylic acids
    • C08F18/04—Vinyl esters
    • C08F18/10—Vinyl esters of monocarboxylic acids containing three or more carbon atoms
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
    • C09D131/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Epoxy Resins (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Synthetic resins curable by heat with or without a polyfunctional compound are prepared by copolymerization of one or more alkenyl esters of saturated aliphatic C9- 19 monocarboxylic acids in which the carboxyl groups are attached direct to tertiary and/or quarernary carbon atoms, with one or more olefinically unsaturated compounds containing as reactive groups hydroxyl, epoxy, carboxyl, carboxylic anhydride, isocyanate, carbamyl, hydroxymethylcarbamyl and/or alkoxymethylcarbamyl groups. Specified alkenyl esters are the vinyl and allyl esters of acids prepared by reacting olefins with formic acid or with carbon monoxide and water. Many suitable comonomers containing reactive groups are listed including alkenols, alkenyl esters of hydroxy acids, partial akenyl ethers of polyhydric compounds, hydroxyalkyl and glycidyl esters of olefinically unsaturated acids, alkenyl esters of epoxy acids, alkenyl glycidyl ethers, olefinically unsaturated carboxylic acids and anhydrides, partial alkenyl esters of polycarboxylic acids, unsaturated amides and alkenyl isocyanates. Comonomers not containing reactive groups, e.g. alkenes and vinyl aromatic compounds, unsaturated esters and nitriles and vinyl halides, may also be present. Polymerization may be effected batchwise or continuously in bulk, solution, suspension or emulsion, in the presence of catalysts, e.g. organic peroxides, azo compounds and redox systems. Polymers containing carbamyl groups may be reacted with aldehydes, optionally together with alcohols, and polymers containing carboxyl and/or carboxylic anhydride groups may be reacted with epoxides. Polymers containing hydroxyl and/or carboxyl groups may be cured with phenol/formaldehyde, urea/formaldehyde or melamine/formaldehyde resins. The compositions may also comprise curing catalysts, e.g. p-toluene sulphonic acid and boron trifluoride. Examples describe curable coating compositions comprising (I) a copolymer of vinyl esters of C9- 11 branched acids, allyl glycolate and vinyl acetate, urea/formaldehyde resin, butanol and p-toluenesulphonic acid; (II) a copolymer of vinyl esters of C9- 11 branched acids, allyl hydroxystearate and vinyl pivalate, melamine/formaldehyde resin, xylene, butanol and p-toluenesulphonic acid; (III) a copolymer of vinyl esters of C9- 11 branched acids and acrylic acid, an epoxy resin based on diphenylol propane, xylene, n-butanol and cyclohexane; (IV) a copolymer of vinyl esters of C9- 11 branched acids, monoallyl phthalate and monoallyl ether of trimethylolpropane, melamine/formaldehyde resin and xylene; (V) a copolymer of vinyl esters of C9- 11 branched acids and monoallyl phthalate, urea/formaldehyde resin, epoxy resin, butanol and benzene; (VI) a butoxymethylated copolymer of vinyl esters of C9- 11 branched acids and acrylamide, toluene and benzene; (VII) a copolymer of vinyl esters of C9- 11 branched acids, methyl methacrylate, acrylic acid and glycidyl acrylate; (VIII) a copolymer of vinyl esters of C9- 11 branched acids and maleic anhydride, urea/formaldehyde resin, xylene and butanol; (IX) a copolymer of vinyl esters of C9- 11 branched acids and maleic anhydride reacted with glycidyl esters of C9- 11 branched acids, urea/formaldehyde resin and butanol; (X) a copolymer of vinyl esters of C9 branched acids and allyl glycidyl ether, butyl acetate and benzyldimethylamine; and (XI) a copolymer of vinyl esters of C9 branched acids and methacrylic acid reacted with glycidyl esters of C9- 11 branched acids, melamine/formaldehyde resin, butanol and butyl acetate.ALSO:Substrates are coated with curable resin compositions containing macromolecular compounds prepared by copolymerization of one or more alkenyl esters of saturated aliphatic C9-19 monocarboxylic acids in which the carboxyl groups are attached direct to tertiary and/or quaternary carbon atoms, with one or more olefinically unsaturated compounds containing as reactive groups hydroxyl, epoxy, carboxyl, carboxylic anhydride; isocyanate, carbamyl, hydroxymethyl carbamyl and/or alkoxymethyl carbamyl groups. In examples steel panels are coated with curable compositions comprising (I) a copolymer of vinyl esters of C9-11 branched acids, allyl glycolate and vinyl acetate, urea/formaldehyde resin, butanol and p-toluene sulphonic acid; (II) a copolymer of vinyl esters of C9-11 branched acids, allyl hydroxystearate and vinyl pivalate, melamine/formaldehyde resin, xylene, butanol and p-toluenesulphonic acid; (III) a copolymer of vinyl esters of C9-11 branched acids and acrylic acid, an epoxy resin based on diphenylolpropane, xylene, butanol and cyclohexane; (IV) a copolymer of vinyl esters of C9-11 branched acids, monoallyl phthalate and monoallyl ether of trimethylolpropane, melamine/formaldehyde resin and xylene; (V) a copolymer of vinyl esters of C9-11 branched acids and monoallyl phthalate, urea/formaldehyde resin, epoxy resin, butanol and benzene; (VI) a butoxymethylated copolymer of vinyl esters of C9-11 branched acids and acrylamide, toluene and benzene; (VII) a copolymer of vinyl esters of C9-11 branched acids, methyl methacrylate, acrylic acid and glycidyl acrylate; (VIII) tin plate coated with a copolymer of vinyl esters of C9-11 branched acids and maleic anhydride, urea/formaldehyde resin, xylene and butanol; (IX) a copolymer of vinyl esters of C9-11 branched acids and maleic anhydride reacted with glycidyl esters of C9-11 branched acids, urea/formaldehyde resin and butanol; (X) a copolymer of vinyl esters of C9 branched acids and allyl glycidyl ether, butyl acetate and benzyldimethylamine; and (XI) a copolymer of vinyl esters of C9 branched acids and methacrylic acid reacted with glycidyl esters of C9-11 branched acids, melamine/formaldehyde resin, butanol and butyl acetate. The coatings are cured at elevated temperature.
GB984064A 1963-03-11 1964-03-09 Process for the preparation of curable compositions of alkenyl resins Expired GB1023295A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL290025 1963-03-11

Publications (1)

Publication Number Publication Date
GB1023295A true GB1023295A (en) 1966-03-23

Family

ID=19754505

Family Applications (1)

Application Number Title Priority Date Filing Date
GB984064A Expired GB1023295A (en) 1963-03-11 1964-03-09 Process for the preparation of curable compositions of alkenyl resins

Country Status (8)

Country Link
BE (1) BE644921A (en)
CH (1) CH449969A (en)
DE (1) DE1494521C3 (en)
DK (1) DK115580B (en)
ES (1) ES297417A1 (en)
GB (1) GB1023295A (en)
NL (2) NL135761C (en)
SE (1) SE301550B (en)

Also Published As

Publication number Publication date
DE1494521B2 (en) 1974-11-21
SE301550B (en) 1968-06-10
DE1494521A1 (en) 1972-03-09
DK115580B (en) 1969-10-20
ES297417A1 (en) 1964-09-01
NL290025A (en)
DE1494521C3 (en) 1975-06-26
CH449969A (en) 1968-01-15
BE644921A (en) 1964-09-09
NL135761C (en)

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