GB1073906A - Method of manufacturing resinoids - Google Patents

Method of manufacturing resinoids

Info

Publication number
GB1073906A
GB1073906A GB4138564A GB4138564A GB1073906A GB 1073906 A GB1073906 A GB 1073906A GB 4138564 A GB4138564 A GB 4138564A GB 4138564 A GB4138564 A GB 4138564A GB 1073906 A GB1073906 A GB 1073906A
Authority
GB
United Kingdom
Prior art keywords
methylol
resin
butylated
bisphenol
butylated methylol
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
GB4138564A
Inventor
Shigeyoshi Tanaka
Toshiro Minami
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.)
Showa Denko Materials Co ltd
Original Assignee
Hitachi Chemical Co 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 Hitachi Chemical Co Ltd filed Critical Hitachi Chemical Co Ltd
Publication of GB1073906A publication Critical patent/GB1073906A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/04—Polymerisation in solution
    • C08F2/06—Organic solvent
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • 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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Abstract

Resins are made by solution copolymerization of two "vinyl" components (1) 4 to 40 parts by weight of a mixture of 2 to 20 parts by weight a ,b -unsaturated monocarboxylic acid and 2 to 20 parts by weight of one or more a ,b -unsaturated monocarboxylic amide or N-C1- 4 alkyl derivatives thereof and (2) 30 to 80 parts by weight of other "vinyl" compounds, in the presence of 3 to 35 parts by weight of epoxide having an epoxy equivalent of 50 to 4000, and a polymerization catalyst, component (1) providing 0.5 to 4.0 functional group equivalents per epoxy equivalent. Suitable epoxides are condensates of epichlorohydrin with bisphenol-A, ethylene glycol or glycerol, epoxidized vegetable oils, the 3,4-epoxy-6-methylcyclohexylmethyl ester of 3,4-epoxy-6-methylcyclohexane carboxylic acid and the 3,4-epoxycyclohexyl methyl ester of 3,4-epoxycyclohexane carboxylic acid. Specified acids are acrylic and methacrylic acid. Specified amides are acrylamide, methacrylamide and the N-methyl, N-ethyl, N-n-propyl and N-n-butyl derivatives thereof. Other vinyl compounds are styrene, a -methyl styrene, vinyl toluene, acrylonitrile, methacrylonitrile, vinyl acetate, alkyl vinyl ethers and C1- 12 alkyl acrylates and methacrylates. Specified catalysts are benzoyl peroxide, di-t.-butyl peroxide, cumene hydroperoxide and azodiisobutyronitrile. Specified solvents are alcohols, toluene, xylene, methylethylketone, butoxyethanol, dioxane and mixtures. The products are useful in heat curable coating compositions, and may be compounded with pigments, e.g. titanium dioxide; and alkyletherified amine/aldehyde and phenol/aldehyde resins, e.g. methylated methylolurea, methylol - N,N1 - ethyleneurea, methyloldicyandiamide, methylolmelamine and methylolbenzoguanamine; butylated methylol-N,N1-ethyleneurea, methyloldicyandiamide and methylolbenzoguanamine; and butylated methylol p-octylphenol, methylol p-t.-butyl phenol, methylol p-cyclohexylphenol, methylol bisphenol-A, methylol o-cresol, methylol m-cresol and methylol p-cresol. In examples resins are prepared by polymerizing acrylamide with (1) styrene, ethyl acrylate and methacrylic acid, (2) methyl methacrylate, ethyl acrylate and methacrylic acid and (3) vinyl toluene, n-butyl acrylate and acrylic acid, in the presence of epichlorohydrin/bisphenol-A condensates. Coating compositions are prepared from (4) resin (1), butylated methylol melamine and titanium dioxide; (5) resin (1), butylated methylol melamine, butylated methylol urea and titanium dioxide; (6) resin (2), methylated methylol benzoguanamine and titanium dioxide; (7) resin (3), butylated methylol melamine and titanium dioxide; resin (1) and (8) butylated methylol bisphenol-A or (9) butylated methylol p-t.-butyl phenol; resin (2) and (10) butylated methylol m-cresol or (11) butylated methylol bisphenol-A; (12) resin (1), butylated methylol melamine and butylated methylol bisphenol-A; (13) resin (2), butylated methylol benzoguanamine and butylated methylol bisphenol-A; and (14) resin 3, butylated methylol urea and butylated methylol p-cresol.ALSO:Metal substrates may be coated with heat curable compositions comprising resins made by solution copolymerisation of two "vinyl" components (1) 4 to 40 parts by weight of a mixture of 2 to 20 parts by weight of a , b -unsaturated monocarboxylic acid and 2 to 20 parts by weight of a , b -unsaturated monocarboxylic amide or N-C1-4 alkyl derivatives thereof and (2) 30 to 80 parts by weight of other "vinyl" compounds, in the presence of 3 to 35 parts by weight of an epoxide having an epoxy equivalent of 50 to 4,000, and a polymerisation catalyst, component (1) providing 0.5 to 4.0 functional group equivalents per epoxy equivalent. The compositions may also comprise pigments, e.g. titanium dioxide, and alkyletherified amine/aldehyde and phenol-aldehyde resins. The substrate may be steel. Specified resin precursors are:- condensates of epichloro-hydrin with bisphenol-A, ethylene glycol or glycerol, epoxidised vegetable oils, the 3,4-epoxy-6-methylcyclo-hexylmethyl ester of 3,4-epoxy-6-methylcyclohexane carboxylic acid and the 3,4-epoxycyclohexylmethyl ester of 3,4-epoxycyclohexane carboxylic acid; acrylic and methacrylic acids; the amides and N-methyl, N-ethyl, N-n-propyl and N-n-butyl derivatives of acrylic and methacrylic acids; styrene, a -methylstyrene, vinyltoluene, acrylonitrile, methacrylonitrile, vinyl acetate, alkyl vinyl ethers, and C1-12 alkyl acrylates and methacrylates. Specified amine and phenol resins are condensates of formaldehyde with urea, N,N\sv-ethylene urea, dicyandiamide, melamine, benzoguanamine, p-octylphenol, p-t-butylphenol, p-cyclohexylphenol, cresols, xylenol and bisphenol-A, etherified with C1-6 alcohols. Examples describe the preparation of resins from epichlorohydrin/bisphenol-A condensates and acryl-amide together with (1) styrene, ethyl acrylate and methacrylic acid, (2) methyl methacrylate, ethyl acrylate and methacrylic acid and (3) vinyl toluene, n-butyl acrylate and acrylic acid, in xylene/butanol solvent; and the coating of steel panels with compositions comprising (4) resin (1), butylated methylol melamine and titanium dioxide; (5) resin (1), butylated methylol melamine, butylated methylol urea and titanium dioxide; (6) resin (2), methylated methylol benzoguanamine and titanium dioxide; (7) resin (3), butylated methylol melamine and titanium dioxide; resin (1) and (8) butylated methylol bisphenol-A or (9) butylated methylol p-t-butylphenol; resin (2) and (10) butylated methylol m-cresol or (11) butylated methylol bisphenol-A; (12) resin (1), butylated methylol melamine and butylated methylol bisphenol-A; (13) resin (2), butylated methylol benzoguanamine and butylated methylol bisphenol-A; and (14) resin (3), butylated methylol urea and butylated methylol p-cresol.
GB4138564A 1964-10-10 1964-10-09 Method of manufacturing resinoids Expired GB1073906A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1317364A CH481153A (en) 1964-10-10 1964-10-10 Process for making resinoids and using the same

Publications (1)

Publication Number Publication Date
GB1073906A true GB1073906A (en) 1967-06-28

Family

ID=4389982

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4138564A Expired GB1073906A (en) 1964-10-10 1964-10-09 Method of manufacturing resinoids

Country Status (2)

Country Link
CH (1) CH481153A (en)
GB (1) GB1073906A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2517320A1 (en) * 1981-12-01 1983-06-03 Illinois Tool Works ACRYLIC / EPOXIDE ADHESIVES, QUICK-TAKING ROOM TEMPERATURE-CURABLE ADHESIVES, AND METHODS OF BONDING
US4708996A (en) * 1983-07-25 1987-11-24 The Dow Chemical Company Stable dispersions of polymers in polyepoxides
US4789712A (en) * 1983-07-25 1988-12-06 The Dow Chemical Company Stable dispersions of polymers in polyepoxides
US5116888A (en) * 1989-09-22 1992-05-26 The Glidden Company Epoxy-acrylic graft copolymers with phosphonium cocatalysts carbon-graft
EP1457524A2 (en) * 2003-03-12 2004-09-15 Surface Specialities Austria GmbH Epoxy resin compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1585486A (en) * 1976-05-11 1981-03-04 Scm Corp Epoxy resins processes for making and using same and substrates coated therewith

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2517320A1 (en) * 1981-12-01 1983-06-03 Illinois Tool Works ACRYLIC / EPOXIDE ADHESIVES, QUICK-TAKING ROOM TEMPERATURE-CURABLE ADHESIVES, AND METHODS OF BONDING
US4708996A (en) * 1983-07-25 1987-11-24 The Dow Chemical Company Stable dispersions of polymers in polyepoxides
US4789712A (en) * 1983-07-25 1988-12-06 The Dow Chemical Company Stable dispersions of polymers in polyepoxides
US5116888A (en) * 1989-09-22 1992-05-26 The Glidden Company Epoxy-acrylic graft copolymers with phosphonium cocatalysts carbon-graft
EP1457524A2 (en) * 2003-03-12 2004-09-15 Surface Specialities Austria GmbH Epoxy resin compositions
EP1457524A3 (en) * 2003-03-12 2004-12-15 Surface Specialities Austria GmbH Epoxy resin compositions

Also Published As

Publication number Publication date
CH481153A (en) 1969-11-15

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