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US4111870A Expired / Lapsed US ⏱️ 0.0 years remaining

Primer composition of an acrylic epoxy ester graft copolymer, a high molecular weight epoxy resin and a heat reactive condensate

Assignee: EIDP Inc
•
Filing: 1977-05-24
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Granted: 1978-09-05
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Expires: 1997-05-24
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Abstract

Abstract A coating composition of film-forming constituents in an organic solvent wherein the film-forming constituents are (1) a graft copolymer having a backbone primarily of methyl methacrylate or styrene and side chains of an epoxy ester of an epoxy resin and dimer fatty acids terminated with monocarboxylic acid. (2) a high molecular weight epoxy hydroxy polyether resin; and (3) a heat reactive condensate such as an alkylated benzoguanamine formaldehyde, an alkylated urea formaldehyde or an alkylate melamine formaldehyde; The coating composition is a high quality primer for metal substrates and is used in the manufacture of automobile and truck bodies.

Inventors

  • 👤 Herman Charles Den Hartog
  • 👤 Aloysius Norbert Walus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 00:38
CPC Classifications
C; C09; C09D; C09D163/00; C09D187/00; C09D187/005; Y; Y10; Y10S; Y10S525/00; Y10S525/93; Y10T; Y10T428/00; Y10T428/26; Y10T428/263; Y10T428/269; Y10T428/31504; Y10T428/31511; Y10T428/31515; Y10T428/31522

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 385 words
A coating composition comprising a solution of 5-60% by weight of film-forming constituents in an organic solvent; wherein the film-forming constituents consist essentially of (1) 20-85% by weight of an acrylic epoxy ester graft copolymer having a relative viscosity of about 1.040-1.100 measured at 0.5% polymer solids in dichloroethylene solvent at 25° C. and consisting essentially of 10-75% by weight of a polymeric backbone segment and 90-25% by weight of polymer side chain segments; wherein (a) the polymeric backbone segment of the graft copolymer consists essentially of polymerized monomers selected from the group consisting of methyl methacrylate, styrene and mixtures thereof; and about 0.5-5% by weight, based on the weight of the copolymer, of polymerized methacrylic acid or acrylic acid monomers; and about 0.5-10% by weight, based on the weight of the copolymer, of polymerized adhesion promoting acrylic monomers selected from the group consisting of hydroxyaminopropyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, 2-aminopropyl methacrylate, 2-aminoethyl methacrylate, t-butyl aminoethyl methacrylate, 2-(1-aziridinyl)-ethyl methacrylate, N-2-hydroxypropyl methacrylamide, N-2-hydroxyethyl methacrylamide and 3-(2-methacryloxyethyl)-2,2-spirocyclohexyloxazolidine; (b) the polymeric side chain segments are grafted into the backbone segment and consist essentially of the following formula which is shown as being grafted into the backbone segment ##STR11## wherein R is H or CH 3; Z is the residual of an epoxy hydroxy polyether resin that has the following recurring structural unit ##STR12## where n is a positive integer sufficiently large to provide a weight average molecular weight of 500-4,000 and R 1 is an alkylene group; X is the residual of a dimer dicarboxylic fatty acid in which the carboxyl groups of the fatty acid are reacted with terminal epoxy groups of th expoxy hydroxy polyether resin; and Y is the residual of an aromatic, cycloaliphatic or aliphatic monocarboxylic acid in which the carboxyl group is reacted with a terminal epoxy group of the epoxy hydroxy polyether resin; (2) 5-70% by weight of an epoxy hydroxy polyether resin of the formula ##STR13## where R 1 is an alkylene group and n is an integer sufficiently large to provide a weight average molecular weight of about 30,000-200,000; and (3) 10-35% by weight of a heat reactive condensate selected from the group consisting of an alkylated melamine formaldehyde, an alkylated urea formaldehyde, an alkylated benzoguanamine formaldehyde or mixtures thereof wherein the alkyl groups have 1-4 carbon atoms. pg,27
Claim 2
Dependent Claim 385 words
A coating composition comprising a solution of 5-60% by weight of film-forming constituents in an organic solvent; wherein the film-forming constituents consist essentially of (1) 20-85% by weight of an acrylic epoxy ester graft copolymer having a relative viscosity of about 1.040-1.100 measured at 0.5% polymer solids in dichloroethylene solvent at 25° C. and consisting essentially of 10-75% by weight of a polymeric backbone segment and 90-25% by weight of polymer side chain segments; wherein (a) the polymeric backbone segment of the graft copolymer consists essentially of polymerized monomers selected from the group consisting of methyl methacrylate, styrene and mixtures thereof; and about 0.5-5% by weight, based on the weight of the copolymer, of polymerized methacrylic acid or acrylic acid monomers; and about 0.5-10% by weight, based on the weight of the copolymer, of polymerized adhesion promoting acrylic monomers selected from the group consisting of hydroxyaminopropyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, 2-aminopropyl methacrylate, 2-aminoethyl methacrylate, t-butyl aminoethyl methacrylate, 2-(1-aziridinyl)-ethyl methacrylate, N-2-hydroxypropyl methacrylamide, N-2-hydroxyethyl methacrylamide and 3-(2-methacryloxyethyl)-2,2-spirocyclohexyloxazolidine; (b) the polymeric side chain segments are grafted into the backbone segment and consist essentially of the following formula which is shown as being grafted into the backbone segment ##STR11## wherein R is H or CH 3; Z is the residual of an epoxy hydroxy polyether resin that has the following recurring structural unit ##STR12## where n is a positive integer sufficiently large to provide a weight average molecular weight of 500-4,000 and R 1 is an alkylene group; X is the residual of a dimer dicarboxylic fatty acid in which the carboxyl groups of the fatty acid are reacted with terminal epoxy groups of th expoxy hydroxy polyether resin; and Y is the residual of an aromatic, cycloaliphatic or aliphatic monocarboxylic acid in which the carboxyl group is reacted with a terminal epoxy group of the epoxy hydroxy polyether resin; (2) 5-70% by weight of an epoxy hydroxy polyether resin of the formula ##STR13## where R 1 is an alkylene group and n is an integer sufficiently large to provide a weight average molecular weight of about 30,000-200,000; and (3) 10-35% by weight of a heat reactive condensate selected from the group consisting of an alkylated melamine formaldehyde, an alkylated urea formaldehyde, an alkylated benzoguanamine formaldehyde or mixtures thereof wherein the alkyl groups have 1-4 carbon atoms. pg,27
Claim 3
Dependent Claim 16 words
The coating composition of claim 1 containing pigment in a pigment volume concentration of about 0.1-60%.
Claim 4
Dependent Claim 20 words
The coating composition of claim 2 in which the pigment consists essentially of titanium dioxide, carbon black and aluminum silicate.
Claim 5
Dependent Claim 16 words
The coating composition of claim 3 in which R 1 is either CH 2 or ##STR14##
Claim 6
Dependent Claim 23 words
The coating composition of claim 4 in which the heat reactive condensate is a mixture of methylated urea formaldehyde and butylated benzoguanamine formaldehyde.
Claim 7
Dependent Claim 16 words
The coating composition of claim 4 in which the heat reactive condensate is methylated urea formaldehyde.
Claim 8
Dependent Claim 27 words
The coating composition of claim 4 in which the adhesion promoting acrylic monomers are selected from the group consisting of tertiary butylamino ethyl methacrylate and diethylaminoethyl methacrylate.
Claim 9
Dependent Claim 38 words
The coating composition of claim 4 containing about 0.5-3.0% by weight, based on the weight of the film forming constituents, of cellulose acetate butyrate having a butyryl content of 17-55% by weight and a viscosity of 1-6 seconds.
Claim 10
Dependent Claim 14 words
The coating composition of claim 4 in which the monocarboxylic acid is benzoic acid.
Claim 11
Dependent Claim 169 words
The coating composition of claim 3 in which the film-forming constituents consist essentially of (1) 55-65% by weight of the acrylic epoxy ester graft copolymer comprises 30-50% by weight of backbone segment and 70-50% by weight of side chain segment, (a) the polymeric backbone segment consist essentially of methyl methacrylate acrylic acid and diethylaminoethyl methacrylate; and (b) the polymeric side chains consist essentially of residual of an epoxy hydroxy polyether resin in which R 1 is ##STR15## and where n is sufficiently large to provide a weight average molecular weight of about 1500 to 3500; and X is the residual of a dimer dicarboxylic fatty acid in which the dimerization product is of 18 carbon atom fatty acids; and Y is the residual of benzoic acid (2) 15-25% by weight of an epoxy hydroxy polyether resin in which R 1 is ##STR16## and having a weight average molecular weight of about 30,000-100,000; (3) 5-15% by weight of butylated benzoguanamine formaldehyde; and (4) 5-15% by weight of methylated urea formaldehyde.
Claim 12
Dependent Claim 153 words
The coating composition of claim 3 in which the film-forming constituents consist essentially of (1) 35-45% by weight of the acrylic epoxy ester graft copolymer wherein (a) the polymeric backbone segment consist essentially of methyl methacrylate, acrylic acid and diethylaminoethyl methacrylate; and (b) the polymeric side chains consist essentially of the residual of an epoxy hydroxy polyether resin in which R 1 is ##STR17## and where n is sufficiently large to provide a weight average molecular weight of about 1500 to 3500; and X the residual of a dimer dicarboxylic fatty acid in which the dimerization product is of 18 carbon fatty acids; and Y is the residual of benzoic acid (2) 35-45% by weight of an epoxy hydroxy polyether resin in which R 1 is ##STR18## and having a weight average molecular weight of about 30,000-100,000; (3) 5-15% by weight of methylated urea formaldehyde; (4) 5-15% by weight of butylated benzoguanamine formaldehyde.
Claim 13
Dependent Claim 146 words
The coating composition of claim 3 in which the film-forming constituents consist essentially of (1) 55-65% by weight of the acrylic epoxy ester graft copolymer wherein (a) the polymeric backbone segment consist essentially of methyl methacrylate, acrylic acid and diethylaminoethyl methacrylate; and (b) the polymeric side chains consist essentially of the residual of an epoxy hydroxy polyether resin in which R 1 is ##STR19## and where n is sufficiently large to provide a weight average molecular weight of about 1500 to 3500; and X the residual of a dimer dicarboxylic fatty acid in which the dimerization product is of 18 carbon fatty acids; and Y is the residual of benzoic acid (2) 10-35% by weight of an epoxy hydroxy polyether resin in which R 1 is ##STR20## and having a weight average molecular weight of about 30,000-100,000; P1 (3) 15-25% by weight of methylated urea formaldehyde.
Claim 14
Dependent Claim 36 words
The coating composition of claim 12 containing 0.5-3% by weight, based on the weight of the film-forming constituents, of cellulose acetate butyrate having a butyryl content of 17-55% by weight and a viscosity of 1-6 seconds.
Claim 15
Dependent Claim 18 words
A metal substrate coated with a 0.5-5.0 mil thick layer of a dried cured composition of claim 1.
Claim 16
Dependent Claim 37 words
A phosphatized steel sheet coated with a 1.0-3.0 mil thick layer of a dried cured composition of claim 3 and having superimposed thereon a 1-5 mil thick layer of a dried coalesced or cured acrylic coating composition.

References Cited (Backward Citations)

US3276905A Cited
US3272647A Cited
US3509086A Cited
US3707516A Cited
US3816557A Cited
US3819567A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-09-04 1982-03-06 1982-09-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-09-04 1986-03-06 1986-09-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-09-04 1990-03-06 1990-09-05 $7700.00 Window Closed / Lapsed

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