WO1988005441A1 - Thermoset acrylic coatings having improved gloss retention - Google Patents
Thermoset acrylic coatings having improved gloss retention Download PDFInfo
- Publication number
- WO1988005441A1 WO1988005441A1 PCT/US1987/000092 US8700092W WO8805441A1 WO 1988005441 A1 WO1988005441 A1 WO 1988005441A1 US 8700092 W US8700092 W US 8700092W WO 8805441 A1 WO8805441 A1 WO 8805441A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- weight
- percent
- amount
- total weight
- Prior art date
Links
Classifications
-
- 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
- C09D131/04—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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- 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
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
Definitions
- the present invention pertains to acrylic polymers containing hydroxybutyl acrylate and to coatings prepared therefrom.
- Thermoset acrylic coatings have been employed in the automobile industry for top coatings on automobiles. While these coatings are very durable and withstand extreme variations in temperature and moisture environments, there is a need to improve their weatherability in terms of gloss retention.
- the present invention provides a method for improving the gloss retention of thermoset acrylic coatings by replacing at least a portion of the hydroxy functional component with hydroxybutyl acrylate or hydroxybutyl methacrylate or a combination thereof.
- One aspect of the present invention concerns an acrylic polymeric composition comprising
- aromatic and aryl shall refer to "the six-carbon ring characteristic of the molecules of all organic compounds of benzene and related series, or the condensed six-carbon rings of naphthalene, anthracene, phenanthrene, etc.” as defined by the CONDENSED
- Another aspect of the present invention pertains to an acrylic coating composition
- an acrylic coating composition comprising
- Another aspect of the present invention pertains to an article coated with one or more layers of the aforementioned acrylic coating compositions.
- the acrylic polymers of the present invention can be prepared by polymerizing a mixture of the monomers in the presence of a suitable catalyst or mixture of catalysts and In the presence of a suitable solvent or mixture of solvents.
- the temperature can be from 70°C to 165°C, preferably from 125°C to 150°C.
- Suitable polymerizable monoethylenically unsaturated monocarboxylic acids which can be employed herein include, for example, acrylic acid, methacrylic acid, crotonic acid, vinyl benzoic acid, or mixtures thereof.
- Suitable polymerizable alkyl or aryl esters of monounsaturated monocarboxylic acids which can be employed herein include, for example, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, amyl acrylate, amyl methacrylate, hexyl acrylate, hexyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, or mixtures thereof.
- Suitable polymerizable monoethylenically unsaturated esters of saturated aliphatic or aromatic monocarboxylic acids which can be employed herein include, for example, vinyl acetate, vinyl propionate, vinyl benzoate, allyl acetate, allyl propionate, allyl benzoate, or mixtures thereof.
- Suitable hydroxyalkyl esters of monoethylenically unsaturated monocarboxylic acids which can be employed herein include, for example, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, or mixtures thereof.
- Suitable polymerizable alkyl or aryl esters of monoethylenically unsaturated dicarboxylic acids which can be employed herein include, for example, diethyl maleate, dibutyl maleate, diethyl fumarate, dibutyl fumarate, di (2-ethylhexyl) maleate, di(2-ethyl- hexyl) fumarate, or mixtures thereof.
- Suitable polymerizable monoethylenically unsaturated aromatic monomers which can be employed herein include, for example, styrene, a methyl styrene, t-butyl styrene, chlorostyrene, vinyl toluene, or mixtures thereof.
- Suitable solvents which can be employed herein include, for example, aliphatic esters, alcohols, ketones, aromatic hydrocarbons, C 8 to C 12 aliphatic or cycloaliphatic hydrocarbons, hydroxyethers, glycol ethers, alkoxycarboxylic esters, or mixtures thereof.
- Particularly suitable solvents include, for example, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, octyl acetate, toluene, xylene, methyl ethyl ketone, methyl propyl ketone, methyl butyl ketone, methyl amyl ketone, 2-ethoxyethyl acetate, 1-methoxypropyl-2-acetate, n-butanol, 1-methoxypropyl-2-propio- nate, 1-methoxypropyl-2-butyrate, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 2-butyoxyethanol, 2-ethoxyethanol, octane, nonane, decane, undecane, dodecane, or mixtures thereof.
- Suitable polymerization catalysts or initiators which can be employed herein include, for example, organic peroxide and organic azo compounds such as, for example, dicumyl peroxide, t-butyl peracetate, benzoyl peroxide, di-t-butyl peroxide, tertbutylazo(lsovalero- nitrlle) ethyl 3,3-di(t-amylperoxy)butyrate, 2,4- pentane- dione peroxide, 1,1'-azobis(cyclohexane carbonitrlle), or mixtures thereof.
- organic peroxide and organic azo compounds such as, for example, dicumyl peroxide, t-butyl peracetate, benzoyl peroxide, di-t-butyl peroxide, tertbutylazo(lsovalero- nitrlle) ethyl 3,3-di(t-amylperoxy)butyrate, 2,
- Suitable curing agents which can be employed herein include, for example, melamine-formaldehyde resins, particularly the methylated form, hexamethoxymethyl melamine, or the mixed methylated/butylated forms; urea-formaldehyde resins; or poly(isocyanate) compounds, such as isophorone diisocyanate as the free Isocyanate or in the blocked form, or mixtures thereof.
- Particularly suitable curing agents include, for example, hexamethoxymethyl melamine.
- the coatings can be cured by heating at temperatures of from 70°C to 150°C, preferably from 100°C to 125°C in the presence of a suitable catalyst.
- the coating compositions of the present invention can be applied to any suitable substrate which can withstand the curing conditions. They are particularly suitable for coating metals, previously coated metals, composite structures such as polyester- -fiber glass, epoxy resin-fiber glass, extruded plastic objects having softening points above the bake temperatures and the like.
- the coat i ng compos i t ions of the present invention can also contain, if desired, pigments, fillers, dyes, flow and leveling agents, flatting agents, curing catalysts, and the like in any combination.
- the copolymer prepared In A above was formulated Into a white baking enamel by blending in a one pint (237 ml) paint can by means of a high-shear mechanical disperser, known as a Cowels Dissolver, the following components.
- the five enamels prepared as above were air- sprayed onto primed 24-gauge (0.7 mm) Bonderite 40 panels to give dry-film thicknesses of 1.5-2.0 mils (0.0381-0.0508 mm) after baking 20 minutes at 150°C. These coated panels were then exposed outdoors on a rack facing south and inclined 45° to the vertical, in Freeport, Texas. The panels were tested after twenty months' exposure for gloss retention and after thirty months' exposure for gloss retention and chalking. The results are given in the following Tables II and III. The thirty month evaluation was more detailed than the twenty month evaluation. The gloss measurements were taken as is, after rinsing with deionized water, and after washing with deionized water and a soft cotton cloth. Gloss measurements were made at both 60° and 20°C. The coatings were tested for chalking before rinsing and the forward impact resistance was measured for comparison to the original values.
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)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The weatherability of acrylic coatings is enhanced by incorporating into the acrylic polymer 2-hydroxybutyl acrylate or 2-hydroxybutyl methacrylate.
Description
THERMOSET ACRYLIC COATINGS HAVING IMPROVED GLOSS RETENTION
The present invention pertains to acrylic polymers containing hydroxybutyl acrylate and to coatings prepared therefrom.
Thermoset acrylic coatings have been employed in the automobile industry for top coatings on automobiles. While these coatings are very durable and withstand extreme variations in temperature and moisture environments, there is a need to improve their weatherability in terms of gloss retention.
The present invention provides a method for improving the gloss retention of thermoset acrylic coatings by replacing at least a portion of the hydroxy functional component with hydroxybutyl acrylate or hydroxybutyl methacrylate or a combination thereof.
One aspect of the present invention concerns an acrylic polymeric composition comprising
(I) a curable polymer resulting from polyermizing a monomer composition consisting of
(A) at least one polymerizable
monoethylenically unsaturated ester of a saturated aliphatic or aromatic monocarboxylic acid in an amount of from 0 to 40, preferably 0 to 14, percent by weight of the total weight of the monomer composition;
(B) at least one polymerizable alkyl or aryl ester of a monoethylenically unsaturated monocarboxylic acid in an amount of from 30 to 60, preferably 40 to 54, percent by weight of the total weight of the monomer composition;
(C) at least one polymerizable hydroxyalkyl ester of a monoethylenically unsaturated monocarboxylic acid in an amount of from 10 to 40, preferably 25 to 39. percent by weight of the total weight of the monomer composition,
(D) at least one polymerizable monoethylenically unsaturated monocarboxylic acid free of ester groups in an amount of from 0 to 3, preferably 1 to 2, percent by weight of the total weight of the monomer composition;
(E) acrylonitrile, methyacrylonitrile or mixture thereof in an amount of from 0 to 15, preferably 0 to 14, percent by weight of the total weight of the monomer composition; (F) at least one polymerizable alkyl or aryl ester of a monoethylenically
unsaturated dicarboxylic acid in an amount of from 0 to 20, preferably 0 to 14, percent by weight of the total weight of the monomer composition; and (G) at least one polymerizable monoethylenically unsaturated aromatic monomer free of acid and ester groups in an amount of from 0 to 50, preferably 20 to 34, percent by weight of the total weight of the monomer composition; and (II) a suitable solvent or mixture of solvents wherein component(I) is present in an amount of from 40 to 80, preferably 65 to 75, percent by weight of the total weight of the polymeric composition and component (II) is present in an amount of from 20 to 60, preferably 25 to 35, percent by weight of the total weight of the polymeric composition characterized by employing 2- hydroxybutyl acrylate or 2-hydroxybutyl methacrylate or a combination thereof as at least a portion of component (C) in an amount such that at least 75 equivalent percent of the hydroxyl groups contained in component (C) is derived from 2- hydroxybutyl acrylate, 2-hydroxybutyl methacrylate or a combination thereof.
For the purposes of this application, the terms "aromatic" and "aryl" shall refer to "the six-carbon ring characteristic of the molecules of all organic compounds of benzene and related series, or the
condensed six-carbon rings of naphthalene, anthracene, phenanthrene, etc." as defined by the CONDENSED
CHEMICAL DICTIONARY, Reinhold Publishing Corp., page
108 for "aromatic nucleus" and page 112 for "aryl".
Another aspect of the present invention pertains to an acrylic coating composition comprising
(A) one or more of the aforementioned polymeric compositions and (B) a curing quantity of one or more curing agents for component (A).
Another aspect of the present invention pertains to an article coated with one or more layers of the aforementioned acrylic coating compositions.
The acrylic polymers of the present invention can be prepared by polymerizing a mixture of the monomers in the presence of a suitable catalyst or mixture of catalysts and In the presence of a suitable solvent or mixture of solvents. The temperature can be from 70°C to 165°C, preferably from 125°C to 150°C.
Suitable polymerizable monoethylenically unsaturated monocarboxylic acids which can be employed herein include, for example, acrylic acid, methacrylic acid, crotonic acid, vinyl benzoic acid, or mixtures thereof.
Suitable polymerizable alkyl or aryl esters of monounsaturated monocarboxylic acids which can be employed herein Include, for example, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, amyl acrylate, amyl methacrylate, hexyl acrylate, hexyl
methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, or mixtures thereof.
Suitable polymerizable monoethylenically unsaturated esters of saturated aliphatic or aromatic monocarboxylic acids which can be employed herein include, for example, vinyl acetate, vinyl propionate, vinyl benzoate, allyl acetate, allyl propionate, allyl benzoate, or mixtures thereof.
Suitable hydroxyalkyl esters of monoethylenically unsaturated monocarboxylic acids which can be employed herein include, for example, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, or mixtures thereof.
Suitable polymerizable alkyl or aryl esters of monoethylenically unsaturated dicarboxylic acids which can be employed herein include, for example, diethyl maleate, dibutyl maleate, diethyl fumarate, dibutyl fumarate, di (2-ethylhexyl) maleate, di(2-ethyl- hexyl) fumarate, or mixtures thereof.
Suitable polymerizable monoethylenically unsaturated aromatic monomers which can be employed herein include, for example, styrene, a methyl styrene, t-butyl styrene, chlorostyrene, vinyl toluene, or mixtures thereof.
Suitable solvents which can be employed herein include, for example, aliphatic esters, alcohols, ketones, aromatic hydrocarbons, C8 to C12 aliphatic or cycloaliphatic hydrocarbons, hydroxyethers, glycol ethers, alkoxycarboxylic esters, or mixtures thereof.
Particularly suitable solvents include, for example, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, octyl acetate, toluene, xylene, methyl ethyl ketone, methyl propyl ketone, methyl butyl ketone, methyl amyl ketone, 2-ethoxyethyl acetate, 1-methoxypropyl-2-acetate, n-butanol, 1-methoxypropyl-2-propio- nate, 1-methoxypropyl-2-butyrate, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 2-butyoxyethanol, 2-ethoxyethanol, octane, nonane, decane, undecane, dodecane, or mixtures thereof.
Suitable polymerization catalysts or initiators which can be employed herein include, for example, organic peroxide and organic azo compounds such as, for example, dicumyl peroxide, t-butyl peracetate, benzoyl peroxide, di-t-butyl peroxide, tertbutylazo(lsovalero- nitrlle) ethyl 3,3-di(t-amylperoxy)butyrate, 2,4- pentane- dione peroxide, 1,1'-azobis(cyclohexane carbonitrlle), or mixtures thereof.
Suitable curing agents which can be employed herein include, for example, melamine-formaldehyde resins, particularly the methylated form, hexamethoxymethyl melamine, or the mixed methylated/butylated forms; urea-formaldehyde resins; or poly(isocyanate) compounds, such as isophorone diisocyanate as the free Isocyanate or in the blocked form, or mixtures thereof. Particularly suitable curing agents Include, for example, hexamethoxymethyl melamine.
The coatings can be cured by heating at temperatures of from 70°C to 150°C, preferably from 100°C to 125°C in the presence of a suitable catalyst.
The coating compositions of the present invention can be applied to any suitable substrate which can withstand the curing conditions. They are particularly suitable for coating metals, previously coated metals, composite structures such as polyester- -fiber glass, epoxy resin-fiber glass, extruded plastic objects having softening points above the bake temperatures and the like.
The coat i ng compos i t ions of the present invention can also contain, if desired, pigments, fillers, dyes, flow and leveling agents, flatting agents, curing catalysts, and the like in any combination.
The following examples are illustrative of the invention but are not to be construed as to limiting the scope thereof in any manner.
EXAMPLE 1
A. Preparation of Polymer
In a conventional glass polymerization vessel was charged 257 g of 2-ethoxyethyl acetate solvent.
After heating to reflux temperature (145°C) with stirring, a mixture consisting of 87.6 g of styre-ne,
87.6 g of methyl methacrylate, 265 g of butyl acrylate,
142.5 g(1 hydroxy equivalent) of hydroxybutyl acrylate, 29.4 g of acrylic acid and 18 g of tertbutylazo (isovaleronitrile) was added dropwise over a period of 6.75 hours at 140°C to 150°C. The mixture was maintained at
150°C for 5.25 hours more and then cooled and stored in a suitable container.
The above procedure was repeated substituting one at a time the following hydroxyalkyl acrylate or methacrylate monomers for the hydroxybutyl acrylate.
116.4 g (1 hydroxyl equiv.) of 2-hydroxyethyl acrylate 130.5 g (1 hydroxy equiv.) of 2-hydroxypropyl acrylate 130.5 g (1 hydroxy equiv.) of 2-hydroxyethyl methacrylate 142.5 g (1 hydroxy equiv.) of 2-hydroxypropyl methacrylate
The properties of the resulting copolymers are given in the following Table I.
B. Preparation of White Pigmented Baking Enamel
The copolymer prepared In A above was formulated Into a white baking enamel by blending in a one pint (237 ml) paint can by means of a high-shear mechanical disperser, known as a Cowels Dissolver, the following components.
ENAMEL RECIPE
Pigment Grind
copolymer solution from A above 146 g
Cymel® 325*, curing agent 42.6 g n-butanol, solvent 32.1 g methyl amyl ketone, solvent 17.4 g
Dow-Corning Paint additive #57 0. 6 g 20% p-toluenesulfonic acid in i-propanol 0.11 g
TiPure R-902 TiO, pigment 111 g
*Cymel® 325 is hexamethoxy methyl melamine commercially available from American Cyanamid Co.
Diluent
methyl amyl ketone to provide the coating with a viscosity of 120 cp (0.12 Pa"s)
C. Coating Substrate and Baking Enamel
The five enamels prepared as above were air- sprayed onto primed 24-gauge (0.7 mm) Bonderite 40 panels to give dry-film thicknesses of 1.5-2.0 mils (0.0381-0.0508 mm) after baking 20 minutes at 150°C. These coated panels were then exposed outdoors on a rack facing south and inclined 45° to the vertical, in Freeport, Texas. The panels were tested after twenty months' exposure for gloss retention and after thirty months' exposure for gloss retention and chalking. The results are given in the following Tables II and III. The thirty month evaluation was more detailed than the twenty month evaluation. The gloss measurements were taken as is, after rinsing with deionized water, and after washing with deionized water and a soft cotton cloth. Gloss measurements were made at both 60° and 20°C. The coatings were tested for chalking before rinsing and the forward impact resistance was measured for comparison to the original values.
Claims
1. A polymeric composition comprising: (I) a curable polymer resulting from polymerizing a monomer composition consisting of
(A) at least one polymerizable monoethylenically unsaturated ester of a saturated aliphatic or aromatic monocarboxylic acid in an amount of from 0 to 40, preferably 0 to 14, percent by weight of the total weight of the monomer composition;
(B) at least one polymerizable alkyl or aryl ester of a monoethylenically unsaturated monocarboxylic acid in an amount of from 30 to 60, preferably 40 to 54, percent by weight of the total weight of the monomer composition;
(C) at least one polymerizable hydroxyalkyl ester of a monoethylenically unsaturated monocarboxylic acid in an amount of from 10 to 40, preferably 25 to 39, percent by weight of the total weight of the monomer composition, (D) at least one polymerizable monoethylenically unsaturated monocarboxylic acid free of ester groups in an amount of from 0 to 3, preferably 1 to 2, percent by weight of the total weight of the monomer composition;
(E) acrylonitrile, methyacrylonitrile or mixture thereof in an amount of from 0 to 15', preferably 0 to 14, percent by weight of the total weight of the monomer composition;
(F) at least one polymerizable alkyl or aryl ester of a monoethylenically unsaturated dicarboxylic acid in an amount of from 0 to 20, preferably 0 to 14, percent by weight of the total weight of the monomer composition; and
(G) at least one polymerizable monoethylenically unsaturated aromatic monomer free of acid and ester groups in an amount of from 0 to 50, preferably 20 to 34, percent by weight of the total weight of the monomer composition; and
(II) a suitable, solvent or mixture of solvents wherein component(I) is present in an amount of from 40 to 80, preferably 65 to 75, percent by weight of the total weight of the polymeric composition and component (II) is present in an amount of from 20 to 60, preferably 25 to 35, percent by weight of the total weight of the polymeric composition characterized by employing 2- hydroxybutyl acrylate or 2-hydroxybutyl methacrylate or combination thereof as at least a portion of component (C) in an amount such that at least 75 equivalent percent of the hydroxyl groups contained in component (C) is derived from 2- hydroxybutyl acrylate, 2-hydroxybutyl- methacrylate or a combination thereof.
2. The acrylic polymeric composition of Claim 1 wherein
(i) component (I-A) is vinyl acetate, vinyl propionate, vinyl benzoate, or mixture thereof;
(ii) component (I-B) is ethyl acrylate, n- butyl acrylate, i-butyl acrylate, 2- butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, n-butyl methacrylate, octyl methacrylate, or mixture thereof; (iii) component (I-C) is 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate or combination thereof;
(iv) component (I-D) is acrylic acid, methacrylic acid, crotonic acid, vinyl benzole acid, or mixture thereof;
(v) component (I-F) is diethyl maleate, dibutyl maleate, diethyl fumarate, dibutyl fumarate, or mixture thereof;
(vi) component (I-G) is styrene, a methyl styrene, or mixture thereof; and (vii) component (II) is selected from ketones, alcohols, glycol ethers, aromatic hydro carbons, esters, glycol ether-esters, and mixtures thereof.
3. The acrylic polymeric composition of Claim
2 wherein
(i) component (I-A) is vinyl acetate;
(ii) component (I-B) is n-butyl acrylate;
(iii) component (I-D) is acrylic acid; (iv) component (I-E) is acrylonitrile;
(v) component (I-F) is dibutyl maleate;
(vi) component (I-G) is styrene; and
(vii) component (I-C) is 2-hydroxybutyl acrylate.
4. An acrylic coating composition comprising (1) at least one polymer composition of Claim 1 and (2) a curing quantity of one or more curing agents for component (1).
5. An acrylic coating composition of Claim 4 wherein said curing agent is a melamine-formaldehyde resin.
6. An acrylic coating composition of Claim 5 wherein said curing agent is hexamethoxymethyl melamine.
7. An article coated with one or more layers of an acrylic coating composition of any of Claims 4 to 6-
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/779,001 US4654398A (en) | 1985-09-23 | 1985-09-23 | Thermoset acrylic coatings having improved gloss retention |
| JP87500946A JPH02501143A (en) | 1987-01-14 | 1987-01-14 | Thermoset acrylic coating with improved gloss retention |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/779,001 US4654398A (en) | 1985-09-23 | 1985-09-23 | Thermoset acrylic coatings having improved gloss retention |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1988005441A1 true WO1988005441A1 (en) | 1988-07-28 |
Family
ID=25115000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1987/000092 WO1988005441A1 (en) | 1985-09-23 | 1987-01-14 | Thermoset acrylic coatings having improved gloss retention |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU609710B2 (en) |
| WO (1) | WO1988005441A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670512A (en) * | 1986-03-14 | 1987-06-02 | The Dow Chemical Company | Acrylic coating compositions and method therefor |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686172A (en) * | 1951-05-22 | 1954-08-10 | Goodrich Co B F | Tough, strong, and easily processed vinyl chloride interpolymers containing free side-chain hydroxyl groups |
| US3542741A (en) * | 1967-02-23 | 1970-11-24 | Basf Ag | Production of polyisocyanate-hydroxy copolymer coating compositions |
| US3832217A (en) * | 1970-12-15 | 1974-08-27 | Mitsubishi Rayon Co | Process for forming exterior finish coating films for automobile bodies |
| US3844993A (en) * | 1971-06-28 | 1974-10-29 | Du Pont | Floor mop having pivotable handle for changing directions air-drying coating composition of an acrylic enamel and an isocyanate cross-linking agent |
| US3883453A (en) * | 1972-07-11 | 1975-05-13 | Toray Industries | Coating compositions containing acrylic polymers polymerized in the presence of cellulose acetate butyrate |
| US3941912A (en) * | 1973-08-15 | 1976-03-02 | Sumitomo Naugatuck Co., Ltd. | Copolymer latex and paper coating composition thereof |
| DE2460329A1 (en) * | 1974-12-20 | 1976-07-01 | Bayer Ag | LOW MOLECULAR ACRYLATE RESINS WITH LOW DISPERSALITY AND A METHOD FOR THEIR PRODUCTION |
| JPS54126054A (en) * | 1978-03-24 | 1979-09-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
| US4237038A (en) * | 1977-10-24 | 1980-12-02 | Vianova Kunstharz, A.G. | Cathodically depositable resins and process of preparing same |
| US4259224A (en) * | 1976-10-02 | 1981-03-31 | Hoechst Aktiengesellschaft | Copolymer solution of acrylic resin, process for its manufacture and use thereof in reactive lacquers |
| US4435556A (en) * | 1983-03-28 | 1984-03-06 | Masler Iii William F | Method of making and using novel scale inhibiting terpolymer |
| US4440894A (en) * | 1982-10-08 | 1984-04-03 | Desoto, Inc. | Thermosetting vinyl acetate tetrapolymer coatings |
| US4501868A (en) * | 1982-06-28 | 1985-02-26 | Exxon Research & Engineering Co. | Superior solvent blends for synthesis of acrylic resins for high solids coatings |
| US4530957A (en) * | 1983-01-05 | 1985-07-23 | Ford Motor Company | Non-aqueous dispersions based on capped stabilizers and reactants comprising polyfunctional monomers I |
| US4532294A (en) * | 1983-12-07 | 1985-07-30 | Exxon Research & Engineering Co. | Superior high solids coatings |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE34762T1 (en) * | 1984-08-17 | 1988-06-15 | Akzo Nv | LIQUID, CROSSLINKABLE COATING COMPOSITION WITH A HYDROXY GROUP-CONTAINING ADDITION POLYMER AS A BINDER. |
| GB2172292A (en) * | 1985-03-08 | 1986-09-17 | Mitsubishi Rayon Co | Acrylic copolymer coatings |
| JPH01501485A (en) * | 1986-11-24 | 1989-05-25 | イー・アイ・デユポン・ド・ネモアース・アンド・コンパニー | Aqueous polymer dispersion for use in automotive base coats under solvent clear coats |
-
1987
- 1987-01-14 WO PCT/US1987/000092 patent/WO1988005441A1/en unknown
- 1987-01-14 AU AU68916/87A patent/AU609710B2/en not_active Ceased
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686172A (en) * | 1951-05-22 | 1954-08-10 | Goodrich Co B F | Tough, strong, and easily processed vinyl chloride interpolymers containing free side-chain hydroxyl groups |
| US3542741A (en) * | 1967-02-23 | 1970-11-24 | Basf Ag | Production of polyisocyanate-hydroxy copolymer coating compositions |
| US3832217A (en) * | 1970-12-15 | 1974-08-27 | Mitsubishi Rayon Co | Process for forming exterior finish coating films for automobile bodies |
| US3844993A (en) * | 1971-06-28 | 1974-10-29 | Du Pont | Floor mop having pivotable handle for changing directions air-drying coating composition of an acrylic enamel and an isocyanate cross-linking agent |
| US3883453A (en) * | 1972-07-11 | 1975-05-13 | Toray Industries | Coating compositions containing acrylic polymers polymerized in the presence of cellulose acetate butyrate |
| US3941912A (en) * | 1973-08-15 | 1976-03-02 | Sumitomo Naugatuck Co., Ltd. | Copolymer latex and paper coating composition thereof |
| DE2460329A1 (en) * | 1974-12-20 | 1976-07-01 | Bayer Ag | LOW MOLECULAR ACRYLATE RESINS WITH LOW DISPERSALITY AND A METHOD FOR THEIR PRODUCTION |
| US4259224A (en) * | 1976-10-02 | 1981-03-31 | Hoechst Aktiengesellschaft | Copolymer solution of acrylic resin, process for its manufacture and use thereof in reactive lacquers |
| US4237038A (en) * | 1977-10-24 | 1980-12-02 | Vianova Kunstharz, A.G. | Cathodically depositable resins and process of preparing same |
| JPS54126054A (en) * | 1978-03-24 | 1979-09-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
| US4501868A (en) * | 1982-06-28 | 1985-02-26 | Exxon Research & Engineering Co. | Superior solvent blends for synthesis of acrylic resins for high solids coatings |
| US4440894A (en) * | 1982-10-08 | 1984-04-03 | Desoto, Inc. | Thermosetting vinyl acetate tetrapolymer coatings |
| US4530957A (en) * | 1983-01-05 | 1985-07-23 | Ford Motor Company | Non-aqueous dispersions based on capped stabilizers and reactants comprising polyfunctional monomers I |
| US4435556A (en) * | 1983-03-28 | 1984-03-06 | Masler Iii William F | Method of making and using novel scale inhibiting terpolymer |
| US4532294A (en) * | 1983-12-07 | 1985-07-30 | Exxon Research & Engineering Co. | Superior high solids coatings |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6891687A (en) | 1988-08-10 |
| AU609710B2 (en) | 1991-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5407707A (en) | Powder coating composition based on epoxy containing polymers and polyacid curing agents | |
| EP0450963B1 (en) | Thermosetting resin composition | |
| US4338379A (en) | High-solids thermosetting enamel coating composition | |
| US3622651A (en) | Novel polymer having pendent ester groups for low temperature bake coatings | |
| US3674734A (en) | Thermosetting acrylic enamel | |
| JPH0312269A (en) | Film forming method | |
| JPH0270772A (en) | Multi-component coating resin which contain anhydride-containing polymer, glycidyl component, and self-stabilizing dispersion resin | |
| GB1576207A (en) | Monomer compositions | |
| US5612434A (en) | Copolymers comprising cyclic or polycyclic monomers having a specific isomer distribution, methods for their manufacture, and their use | |
| US3702836A (en) | Polymer dispersions | |
| US4548963A (en) | Internally crosslinkable acrylic polymers and diglycidyl esters of dibasic acids | |
| US4654398A (en) | Thermoset acrylic coatings having improved gloss retention | |
| US4371667A (en) | Baking lacquer | |
| US5780541A (en) | Nonaqueous paints | |
| US3488307A (en) | Coating compositions comprising mixtures of nitrogen-containing acrylic polymers | |
| GB2169911A (en) | Acrylic resin for use in high solids paints | |
| KR960014552B1 (en) | POLYMERS PREPARED BY POLYMERIZING Ñß,ÑÔ- ETHYLENICALLY UNSATURATED ACIDS AND EPOXY COMPOUNDS | |
| DE69804313T2 (en) | FILM-FORMING COMPOSITION | |
| US3753935A (en) | Nonyellowing acrylic enamel containing an acid phosphate catalyst | |
| NZ200291A (en) | Coating compositions containing hydroxyl-group-containing addition polymer and alkylated melamine-formaldehyde resin | |
| CA2046866C (en) | Coating composition based on an addition polymer containing hydroxyl groups and on an aminoplastic resin crosslinking agent, containing acid catalysts with hydroxyl groups | |
| US4238573A (en) | Methacrylate coating compositions | |
| AU604002B2 (en) | Two component coating composition of an anhydride containing polymer and a clycidyl component | |
| US5068288A (en) | Acid etch resistant clear coats | |
| EP0398387B1 (en) | High solids low VOC paint compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU JP |