US4486555A
Expired / Lapsed
US
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Thermosetting coating composition comprising polymeric catalyst-II
Assignee: EIDP Inc
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Filing: 1982-09-30
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Granted: 1984-12-04
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Expires: 2002-09-30
Abstract
Abstract A novel organic solvent based, thermosetting coating composition comprises novel epoxy ester resin having number average molecular weight (M n ) about 1000 to about 5000 and being the reaction product of diepoxide, for example bisphenol-A epichlorohydrin epoxy resin, with (i) dicarboxylic acid, for example the dimerization reaction product of C-18 fatty acid, in chain extension reaction and (ii) fatty acid, for example Soya fatty acid, in chain terminating esterification reaction, which chain extension reaction and esterification reaction occur at least in part substantially simultaneously. Preferably, catalyst is employed for said chain extension and esterification reactions. The coating composition further comprises polyfunctional aminoplast crosslinking agent, for example, hexamethoxymethylmelamine, and polycarboxy functional polymeric catalyst. Also provided is a method of making a humidity and solvent resistant coating on a substrate, adapted to provide corrosion protection to the substrate, for example, to bare sheet metal of an automotive vehicle body, which method comprises applying the novel coating composition of the invention to the substrate, for example, by spraying techniques, and subjecting the applied coating to an elevated temperature for a time sufficient to cure the coating.
Inventors
- 👤 Panagiotis I. Kordomenos
- 👤 Kenneth R. Kurple
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 22:19
CPC Classifications
C; C09; C09D; C09D163/00; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/066; C08G59/12; C08G59/18; C08G59/68; C09D163/10
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
148 words
A novel, organic solvent based, thermosetting coating composition comprising: A. epoxy ester resin of number average molecular weight (M n ) about 1000 to about 5000, being the reaction product of diepoxide with (i) dicarboxylic acid in chain extension reaction and (ii) monobasic fatty acid in chain terminating esterification reaction, which chain extension and esterification reactions occur substantially simultaneously at a reaction temperature reaching at least about 135° C., wherein the epoxy functionality, dicarboxylic acid carboxyl functionality and fatty acid carboxyl functionality are employed in relative proportions of about 1:0.3-0.8:0.3-0.8 equivalents, respectively; B. polyfunctional aminoplast crosslinking agent; and C. polycarboxy functional polymeric catalyst of number average molecular weight (M n ) about 1,000-10,000 being substantially unreactive at room temperature with the epoxy ester resin and the polyfunctional aminoplast crosslinking agent, in an amount of about 2% to about 15% by weight of resin solids in the coating composition.
Claim 2
Dependent Claim
148 words
A novel, organic solvent based, thermosetting coating composition comprising: A. epoxy ester resin of number average molecular weight (M n ) about 1000 to about 5000, being the reaction product of diepoxide with (i) dicarboxylic acid in chain extension reaction and (ii) monobasic fatty acid in chain terminating esterification reaction, which chain extension and esterification reactions occur substantially simultaneously at a reaction temperature reaching at least about 135° C., wherein the epoxy functionality, dicarboxylic acid carboxyl functionality and fatty acid carboxyl functionality are employed in relative proportions of about 1:0.3-0.8:0.3-0.8 equivalents, respectively; B. polyfunctional aminoplast crosslinking agent; and C. polycarboxy functional polymeric catalyst of number average molecular weight (M n ) about 1,000-10,000 being substantially unreactive at room temperature with the epoxy ester resin and the polyfunctional aminoplast crosslinking agent, in an amount of about 2% to about 15% by weight of resin solids in the coating composition.
Claim 3
Dependent Claim
24 words
The solvent based, thermosetting coating composition of claim 1, wherein said epoxy ester resin number average molecular weight is about 1000 to about 3000.
Claim 4
Dependent Claim
21 words
The solvent based, thermosetting coating composition of claim 2, wherein said diepoxide has a number average molecular weight of about 100-1000.
Claim 5
Dependent Claim
41 words
The solvent based, thermosetting coating composition of claim 1, wherein said diepoxide is selected from the group consisting of bisphenol-A epichlorohydrin epoxy resin, hydantoin epoxy resin, cyclic and acyclic aliphatic diepoxide, and the like and a mixture of any of them.
Claim 6
Dependent Claim
17 words
The solvent based, thermosetting coating composition of claim 1, wherein said diepoxide bears two terminal epoxide groups.
Claim 7
Dependent Claim
19 words
The solvent based, thermosetting coating composition of claim 1, wherein said diepoxide consists essentially of diglycidyl ether bisphenol-A resin.
Claim 8
Dependent Claim
22 words
The solvent based, thermosetting coating composition of claim 1, wherein the dicarboxylic acid has a number average molecular weight of about 145-1000.
Claim 9
Dependent Claim
31 words
The solvent based, thermosetting coating composition of claim 1 or 6, wherein said dicarboxylic acid is saturated or unsaturated, cyclic or acyclic aliphatic or aromatic dicarboxylic acid or a mixture thereof.
Claim 10
Dependent Claim
36 words
The solvent based, thermosetting coating composition of claim 1, wherein said dicarboxylic acid is of the general formula: HOOC--R--COOH wherein R is a divalent linking moiety substantially unreactive with the epoxy functionality of the diepoxide resin.
Claim 11
Dependent Claim
40 words
The solvent based, thermosetting coating composition of claim 9, wherein R is selected from the group consisting of a straight or branched alkylene or alkylidene moiety of about 4 to about 42 carbons and the like and a mixture thereof.
Claim 12
Dependent Claim
18 words
The solvent based, thermosetting coating composition of claim 1, wherein said dicarboxylic acid provides two terminal carboxyl groups.
Claim 13
Dependent Claim
26 words
The solvent based, thermosetting coating composition of claim 1, wherein said dicarboxylic acid consists essentially of substantially saturated, acyclic, aliphatic dimer acid of about 4-42 carbons.
Claim 14
Dependent Claim
25 words
The solvent based, thermosetting coating composition of claim 1, wherein said dicarboxylic acid consists essentially of the dimer acid reaction product of C-18 fatty acid.
Claim 15
Dependent Claim
37 words
The solvent based, thermosetting coating composition of claim 1, wherein said monobasic fatty acid is selected from the group consisting of fatty acids of about 8 to about 18 carbons and a mixture of any of them.
Claim 16
Dependent Claim
23 words
The solvent based, thermosetting coating composition of claim 1, wherein said monobasic fatty acid consists essentially of substantially saturated, acyclic, aliphatic fatty acid.
Claim 17
Dependent Claim
23 words
The solvent based, thermosetting coating composition of claim 1, 6 or 13 wherein said monobasic fatty acid consists essentially of Soya fatty acid.
Claim 18
Dependent Claim
27 words
The solvent based, thermosetting coating composition of claim 16, wherein said polyfunctional aminoplast crosslinking agent consists essentially of hexa(methoxymethyl)melamine or the like or a compatible mixture thereof.
Claim 19
Dependent Claim
29 words
The solvent based, thermosetting coating composition of claim 16, wherein said diepoxide, said dicarboxylic acid and said fatty acid are employed in relative amounts of about 1:0.4-0.6:0.4-0.6 equivalents, respectively.
Claim 20
Dependent Claim
26 words
The solvent based, thermosetting coating composition of claim 1, wherein said polycarboxy functional polymeric catalyst has a number average molecular weight (M n ) about 1,500-3,000.
Claim 21
Dependent Claim
59 words
The solvent based, thermosetting coating composition of claim 1, 6, 13 or 15 wherein said polycarboxy functional polymeric catalyst comprises the reaction product of (i) ethylenically unsaturated carboxylic acid, with (ii) ethylenically unsaturated copolymerization monomer which provides to said reaction product no functionality substantially reactive at room temperature with said epoxy ester resin or said polyfunctional aminoplast crosslinking agent.
Claim 22
Dependent Claim
37 words
The solvent based, thermosetting coating composition of claim 20, wherein said carboxylic acid is selected from the group consisting of acrylic acid, methacrylic acid, butanoic acid and the like and a compatible mixture of any of them.
Claim 23
Dependent Claim
38 words
The solvent based, thermosetting coating composition of claim 21, wherein said copolymerizable monomer is selected from the group consisting of glycidyl acrylate, glycidyl methacrylate, styrene, vinyl ether and the like or a compatible mixture of any of them.
Claim 24
Dependent Claim
40 words
The solvent based, thermosetting coating composition of claim 20, wherein said polycarboxy functional polymeric catalyst consists essentially of the reaction product of about 20-45% by weight of said carboxylic acid monomers with about 55-80% by weight of said copolymerization monomers.
Claim 25
Dependent Claim
36 words
The solvent based, thermosetting coating composition of claim 23, wherein said polycarboxy functional polymeric catalyst consists essentially of the polymerization reaction product of about 30% by weight acrylic acid with about 70% by weight butyl methacrylate.
Claim 26
Dependent Claim
35 words
The solvent based, thermosetting coating composition of claim 1, wherein said polycarboxy functional polymeric catalyst is used in an amount of about 5% to about 10% by weight of resin solids in the coating composition.
Claim 27
Dependent Claim
37 words
The solvent based, thermosetting coating composition of claim 1, wherein said polycarboxy functional polymeric catalyst is used in an amount sufficient to raise the acid level of the epoxy ester resin to about 15 to about 35.
Claim 28
Dependent Claim
31 words
The solvent based, thermosetting coating composition of claim 16, wherein said polycarboxy functional polymeric catalyst is mixed with the epoxy ester resin at a temperature at or above about 105° C.
Claim 29
Dependent Claim
50 words
A sprayable, pigmented high solids primer adapted for use on bare metal substrate, comprising the coating composition of claim 1, 6, 13 or 15 wherein the volatile organic content is less than about 400 g/l and the viscosity no greater than about 35 sec., #4 Ford Cup at 27° C.
Claim 30
Dependent Claim
22 words
The sprayable, pigmented, high solids primer of claim 28 wherein the pigment to resin ratio is about 1:1 to about 2:1, respectively.
Claim 31
Dependent Claim
178 words
A novel, organic solvent based, thermosetting coating compositions comprising: A. epoxy ester resin of number average molecular weight (M n ) about 1000 to about 3000, being the reaction product of diepoxide, consisting essentially of diglycidyl ether bisphenol-A resin, with (i) dicarboxylic acid consisting essentially of the dimer acid reaction product of C-18 fatty acid, in chain extension reaction, (ii) monobasic fatty acid consisting essentially of Soya fatty acid, in chain termination esterification reaction, and (iii) catalyst for said chain extension and esterification reactions, which reactions occur substantially simultaneously at a reaction temperature reaching at least about 135° C., wherein the epoxy functionality, dicarboxylic acid carboxyl functionality and fatty acid carboxyl functionality are employed in relative proportions of about 1:0.4-0.6:0.4-0.6 equivalents, respectively; B. polyfunctional aminoplast crosslinking agent; and C. polycarboxy functional polymeric catalyst of number average molecular weight (M n ) about 1,000-10,000 being substantially unreactive at room temperature with the epoxy ester resin and the polyfunctional aminoplast crosslinking agent, in an amount of about 2% to about 15% by weight of resin solids in the coating composition.
Claim 32
Dependent Claim
178 words
A novel, organic solvent based, thermosetting coating compositions comprising: A. epoxy ester resin of number average molecular weight (M n ) about 1000 to about 3000, being the reaction product of diepoxide, consisting essentially of diglycidyl ether bisphenol-A resin, with (i) dicarboxylic acid consisting essentially of the dimer acid reaction product of C-18 fatty acid, in chain extension reaction, (ii) monobasic fatty acid consisting essentially of Soya fatty acid, in chain termination esterification reaction, and (iii) catalyst for said chain extension and esterification reactions, which reactions occur substantially simultaneously at a reaction temperature reaching at least about 135° C., wherein the epoxy functionality, dicarboxylic acid carboxyl functionality and fatty acid carboxyl functionality are employed in relative proportions of about 1:0.4-0.6:0.4-0.6 equivalents, respectively; B. polyfunctional aminoplast crosslinking agent; and C. polycarboxy functional polymeric catalyst of number average molecular weight (M n ) about 1,000-10,000 being substantially unreactive at room temperature with the epoxy ester resin and the polyfunctional aminoplast crosslinking agent, in an amount of about 2% to about 15% by weight of resin solids in the coating composition.
Claim 33
Dependent Claim
46 words
A sprayable, pigmented, high solids primer adapted for use on bare metal substrate, comprising the coating composition of claim 30 wherein the volatile organic content is less than about 400 g/l and the viscosity no greater than about 35 sec., #4 Ford Cup at 27° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-12-04 | 1988-06-04 | 1988-12-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-04 | 1992-06-04 | 1992-12-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-04 | 1996-06-04 | 1996-12-04 | $7700.00 | Window Closed / Lapsed |