GB1087623A - Thermosetting coating compositions - Google Patents

Thermosetting coating compositions

Info

Publication number
GB1087623A
GB1087623A GB1494166A GB1494166A GB1087623A GB 1087623 A GB1087623 A GB 1087623A GB 1494166 A GB1494166 A GB 1494166A GB 1494166 A GB1494166 A GB 1494166A GB 1087623 A GB1087623 A GB 1087623A
Authority
GB
United Kingdom
Prior art keywords
weight
ester
pigments
alkanol
acids
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
GB1494166A
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.)
Beck Koller and Company England Ltd
Original Assignee
Beck Koller and Company England 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
Application filed by Beck Koller and Company England Ltd filed Critical Beck Koller and Company England Ltd
Publication of GB1087623A publication Critical patent/GB1087623A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D131/00Coating 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
    • C09D131/02Homopolymers or copolymers of esters of monocarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F18/00Homopolymers 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
    • C08F18/02Esters of monocarboxylic acids
    • C08F18/04Vinyl esters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D133/00Coating 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08Homopolymers or copolymers of acrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen

Landscapes

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

Abstract

Thermosetting coating compositions comprise a mixture dissolved in an organic solvent of (A) 55 to 95% by weight of a thermoplastic copolymer obtained by copolymerization of a mixture consisting of (a) 10 to 50% by weight of a versatic acid 911 vinyl ester, (b) 0 to 6% by weight of a copolymerizable a ,b -ethylenically unsaturated mono-, di- and/or poly-carboxylic acid or a partial ester of such a di- or poly-carboxylic acid derived from a C1-C8 alkanol, (c) 20 to 50% by weight of methyl methacrylate, (d) 20 to 50% by weight of an ester of acrylic acid and a C4-C18 alkanol, (e) 5 to 20% by weight of a hydroxyalkyl or hydroxyaralkyl ester of an a ,b -ethylenically unsaturated carboxylic acid; and (B) 5 to 45% by weight of a resin-forming condensate of an aldehyde and urea, N,N1 - ethyleneurea, dicyanodiamide or an aminotriazine, alkylated with cyclohexanol or a C1-C6 alkanol. Specified components (b) are acrylic, methacrylic, ethacrylic, phenylacrylic, maleic, fumaric, itaconic, citraconic and crotonic acids and, where existent, the partial alkyl esters of such acids. Component (e) may be derived from the same acids as used in component (b) and preferably contains at least one primary or secondary hydroxyl group. The aminoplast precondensate is preferably derived from formaldehyde although other aldhydes such as acetaldehyde, crotonaldehyde and acrolein are also suitable. In examples an etherified melamine-formaldehyde product is used. Suitable solvents include aromatic hydrocarbons, aliphatic and cyloaliphatic alcohols and ketones, aliphatic esters and ethers, dioxan, dimethyl formamide, dimethyl acetamide, acetonitrile and nitroalkanes. The composition may also include pigments, extenders and hardening catalysts. Pigments include chrome yellow, Prussian blue, Brunswick green, titanium pigments possibly extended with alkaline earth metal sulphates, titanate salts, zinc compounds, antimony oxide, and organic pigments including calcium and barium lakes and azo dyes. Suitable hardening catalysts include inorganic acids and their ammonium salts and organic acids and their amine salts and certain esters. The copolymers can be prepared by polymerizing the respective monomers in a solvent using a catalyst such as benzoyl peroxide, di-t.-butyl peroxide, t.-butyl hydroperoxide, cumene hydroperoxide or azoisobutyro-nitrile and, if desired, a chain transfer agent, e.g. butyl or lauryl mercaptan or thioglycollic acid.ALSO:Thermosetting compositions suitable for coating vehicle bodies, paper, textiles, leather, wood, synthetic materials, ceramics, bricks, concrete and metals comprise a mixture dissolved in an organic solvent of (A) 55 to 95% of a thermoplastic copolymer of (i) a versatic acid 911 vinyl ester (ii) methyl methacrylate (iii) an ester of acrylic acid with a C4-C18 alkanol (iv) a hydroxyalkyl or hydroxyaralkyl ester of an a , b -ethylenically unsaturated carboxylic acid and, optionally, (v) an a , b -ethylenically unsaturated mono-, di- and/or polycarboxylic acid or a partial ester of such a di- or poly-carboxylic acid with a C1-C8 alkanol; and (B) 5 to 45% by weight of a resin-forming condensate of an aldehyde with urea, N,N\sv-ethyleneurea, dicyanodiamide or an aminotriazine (e.g. melamine), alkylated with cyclohexanol or a C1-C6 alkanol. Suitable solvents include aromatic hydrocarbons, aliphatic and cycloaliphatic alcohols and ketones, aliphatic esters and ethers, dioxan, dimethyl formamide, dimethyl acetamide, acetonitrile and nitroalkanes. The composition may also include pigments, extenders and hardening catalysts. Pigments include chrome yellow, Prussian blue, Brunswick green, titanium pigments possibly extended with alkaline earth metal sulphates, titanate salts, zinc compounds, antimony oxide, and organic pigments including calcium and barium lakes and azo dyes. Suitable hardening catalysts include inorganic acids and their ammonium salts, and organic acids and their amine salts and certain esters. The compositions may be applied in various ways, e.g. by coating, spraying, dipping or roller-coating. The coatings can be dried at room temperature or up to 100 DEG C, and hardened at 80-230 DEG C. In Examples the coatings are applied to iron sheets, deep-drawn metal sheets and phosphated metal sheets.
GB1494166A 1965-07-03 1966-04-04 Thermosetting coating compositions Expired GB1087623A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DER0041011 1965-07-03
DE1965R0041010 DE1289936B (en) 1965-07-03 1965-07-03 Heat-curable coating agents based on organic solvents, thermoplastic copolymers containing hydroxyl groups and amino resins

Publications (1)

Publication Number Publication Date
GB1087623A true GB1087623A (en) 1967-10-18

Family

ID=25991906

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1212266A Expired GB1145564A (en) 1965-07-03 1966-03-18 A process for the production of thermoplastic copolymers
GB1494166A Expired GB1087623A (en) 1965-07-03 1966-04-04 Thermosetting coating compositions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1212266A Expired GB1145564A (en) 1965-07-03 1966-03-18 A process for the production of thermoplastic copolymers

Country Status (3)

Country Link
CH (1) CH493611A (en)
DE (2) DE1289936B (en)
GB (2) GB1145564A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3669942A (en) * 1969-07-03 1972-06-13 Shell Oil Co Copolymers of vinyl esters of branched acids
US4164488A (en) 1974-03-29 1979-08-14 E. I. Du Pont De Nemours And Company Aqueous thermosetting acrylic enamel
US6228941B1 (en) * 1997-12-24 2001-05-08 Shell Oil Company Powder coating of glycidyl-functional copolymer, dicarboxylic acid and acid-functional polyester

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8924983D0 (en) * 1989-11-06 1989-12-28 Shell Int Research Interpolymer latices from esters of(meth)acrylic acid and vinyl esters of branched chain carboxylic acids
GB9013722D0 (en) * 1990-06-20 1990-08-08 Shell Int Research Interpolymer dispersions from vinyl esters of branched chain carboxylic acids and ethylenically unsaturated acids and/or their esters
EP0546640B1 (en) * 1991-12-13 1997-03-05 Shell Internationale Researchmaatschappij B.V. Interpolymer-based binders
US5641829A (en) * 1991-12-30 1997-06-24 Ppg Industries, Inc. Coating compositions prepared from base neutralized, stable aqueous dispersion of hydroxyl functional acrylic polymers
US5464897A (en) * 1991-12-30 1995-11-07 Ppg Industries, Inc. Aqueous fluoropolymer dispersions
US5342878A (en) * 1991-12-30 1994-08-30 Ppg Industries, Inc. Base neutralized, stable, aqueous dispersion of a hydroxyl functional acrylic polymer and coating compositions prepared therefrom
DE4218663A1 (en) * 1992-06-05 1993-12-09 Wacker Chemie Gmbh Coating agent for coating aluminum
US5288828A (en) * 1993-03-08 1994-02-22 The Sherwin-Williams Company Dispersant polymers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681897A (en) * 1950-10-06 1954-06-22 American Cyanamid Co Surface coating compositions comprising aminoplast resins and a thermoplastic copolymer containing a polymerized hydroxy alkyl ester of an alpha, beta ethylenically unsaturated carboxylic acid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3669942A (en) * 1969-07-03 1972-06-13 Shell Oil Co Copolymers of vinyl esters of branched acids
US4164488A (en) 1974-03-29 1979-08-14 E. I. Du Pont De Nemours And Company Aqueous thermosetting acrylic enamel
US6228941B1 (en) * 1997-12-24 2001-05-08 Shell Oil Company Powder coating of glycidyl-functional copolymer, dicarboxylic acid and acid-functional polyester

Also Published As

Publication number Publication date
CH493611A (en) 1970-07-15
DE1595243A1 (en) 1970-01-02
DE1595243B2 (en) 1973-06-28
GB1145564A (en) 1969-03-19
DE1289936B (en) 1969-02-27
DE1595243C3 (en) 1974-01-31

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