US4465815A
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Polyhydroxy oligomers for high solids coatings II
Assignee: EIDP Inc
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Filing: 1981-12-28
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Granted: 1984-08-14
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Expires: 2001-12-28
Abstract
Abstract A novel polyhydroxy oligomer crosslinkable with amine-aldehyde to form a coating composition adapted for use as an automotive topcoat which upon curing forms a hard, glossy, durable coating with outstanding weatherability and excellent resistance to solvents and water. The coating composition comprises: (A) a polyhydroxy oligomer having a number average (M n ) molecular weight of between about 300-2000 and being the reaction product of: (i) an acid ester made by reacting (a) a C 3 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and (ii) a monoepoxide C 2 -C 10 monomer, the monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide groups for each acid group of the acid ester; (B) an amine-aldehyde crosslinking agent; and (C) optionally a hydroxy functional additive. The amine-aldehyde crosslinking agent is included in the composition in an amount sufficient to provide at least about 0.60 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxyl functionality included in the composition either on the polyhydroxy oligomer or as a hydroxyl group of the hydroxy functional additive.
Inventors
- 👤 Mohinder S. Chattha
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 17:22
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4205; C08G18/423; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31681; Y10T428/31688
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
208 words
A thermosetting coating composition adapted for low temperature bake applications comprising: (A) a polyhydroxy oligomer having a number average (M n ) molecular weight of between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester; (B) an amine-aldehyde crosslinking agent; and (C) 0-50 weight percent based on the total weight of (A), (B) and (C) of a hydroxy functional additive having a number average molecular weight (M n ) of between about 150-6000, said amine-aldehyde crosslinking agent being included in said composition in an amount sufficient to provide at least about 0.60 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxyl functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 2
Dependent Claim
208 words
A thermosetting coating composition adapted for low temperature bake applications comprising: (A) a polyhydroxy oligomer having a number average (M n ) molecular weight of between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester; (B) an amine-aldehyde crosslinking agent; and (C) 0-50 weight percent based on the total weight of (A), (B) and (C) of a hydroxy functional additive having a number average molecular weight (M n ) of between about 150-6000, said amine-aldehyde crosslinking agent being included in said composition in an amount sufficient to provide at least about 0.60 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxyl functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 3
Dependent Claim
21 words
A coating composition according to claim 1, wherein the hydroxy groups of said diol are not attached to adjacent carbon atoms.
Claim 4
Dependent Claim
13 words
A coating composition according to claim 2, wherein said diol is 2-ethyl-1,3-hexane diol.
Claim 5
Dependent Claim
27 words
A coating composition according to claim 1, wherein the alkyl group of said alkyl hexahydrophthalic anhydride comprises a lower alkyl group having up to about seven carbons.
Claim 6
Dependent Claim
16 words
A coating composition according to claim 3 or 4, wherein said anhydride is methyl hexahydrophthalic anhydride.
Claim 7
Dependent Claim
31 words
A coating composition according to claim 4, wherein said monoepoxide C 2 -C 10 monomer is selected from the group consisting of alkylene monoepoxides, glycidyl esters, glycidyl ethers, and mixtures thereof.
Claim 8
Dependent Claim
29 words
A coating composition according to claims 1 or 6, wherein said polyhydroxy oligomer is a dihydroxy oligomer and said monoepoxide C 2 -C 10 monomer contains no hydroxyl functionality.
Claim 9
Dependent Claim
15 words
A coating composition according to claim 7, wherein said alkyl hexahydropthalic is methyl hexahydrophthalic anhydride.
Claim 10
Dependent Claim
14 words
A coating composition according to claim 8, wherein said branched diol is 2-ethyl-1,3-hexane diol.
Claim 11
Dependent Claim
14 words
A coating composition according to claim 9, wherein said monoepoxide monomer is propylene oxide.
Claim 12
Dependent Claim
80 words
A coating composition according to claim 1, wherein said amine-aldehyde crosslinking agent is selected from the group consisting of condensation products of formaldehyde with melamine, substituted melamine, urea, benzoguanamine and substituted benzoguanamine, and mixtures of said condensation products in an amount sufficient to provide between about 0.75 and about 3.75 equivalents of nitrogen crosslinking functionalilty for each equivalent of hydroxy functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 13
Dependent Claim
79 words
A coating composition according to claim 1, wherein said hydroxy functional additive is a polyol selected from the group consisting of (i) hydroxy functional polyesters, (ii) hydroxy functional polyethers, (iii) hydroxy functional oligoesters, (iv) monomeric polyols, (v) hydroxy functional copolymers formed from monoethylenically unsaturated monomers, one or more of which bears hydroxy functionality and which is included in said copolymer in amounts ranging from about 10 to about 50 weight percent of said copolymer, and (vi) mixtures of (i)-(v).
Claim 14
Dependent Claim
30 words
A coating composition according to claim 1, wherein said composition further comprises up to 15 weight percent, based on the total weight of said composition, of a flow control additive.
Claim 15
Dependent Claim
43 words
A coating composition according to claim 1, wherein said acid ester is a dicarboxylic acid ester made by combining said diol and said anhydride in the reaction mixture in amounts and under conditions sufficient to result in reaction in a 1:2 molar ratio.
Claim 16
Dependent Claim
14 words
A coating composition according to claim 14, wherein said anhydride is methyl hexadrophthalic anhydride.
Claim 17
Dependent Claim
13 words
A coating composition according to claim 15, wherein said diol is 2-ethyl-1,3-hexane diol.
Claim 18
Dependent Claim
33 words
A coating composition according to claim 14 or 16, wherein said monoepoxide C 2 -C 10 monomer is selected from the group consisting of alkylene monoepoxides, glycidyl ethers, glycidyl esters, and mixtures thereof.
Claim 19
Dependent Claim
15 words
A coating composition according to claim 17, wherein said monoepoxide monomer contains no hydroxy functionality.
Claim 20
Dependent Claim
106 words
A polyhydroxy oligomer having a number average (M n ) molecular weight between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio greater than 1:1 up to 1:2; (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester.
Claim 21
Dependent Claim
106 words
A polyhydroxy oligomer having a number average (M n ) molecular weight between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio greater than 1:1 up to 1:2; (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester.
Claim 22
Dependent Claim
21 words
A polyhydroxy oligomer according to claim 19, wherein the hydroxy groups of said diol are not attached to adjacent carbon atoms.
Claim 23
Dependent Claim
14 words
A polyhydroxy oligomer according to claim 20, wherein said branched diol is 2-ethyl-1,3-hexane diol.
Claim 24
Dependent Claim
23 words
A polyhydroxy oligomer according to claim 19, wherein said alkyl hexahydrophthalic anhydride comprises a lower alkyl group having up to about seven carbons.
Claim 25
Dependent Claim
16 words
A polyhydroxy oligomer according to claim 19 or 21, wherein said anhydride is methyl hexahydrophthalic anhydride.
Claim 26
Dependent Claim
31 words
A polyhydroxy oligomer according to claim 22, wherein said monoepoxide C 2 -C 10 monomer is selected from the group consisting of alkylene monoepoxides, glycidyl esters, glycidyl ethers, and mixtures thereof.
Claim 27
Dependent Claim
29 words
A polyhydroxy oligomer according to claim 19 or 24, wherein said polyhydroxy oligomer is a dihydroxy oligomer and said monoepoxide C 2 -C 10 monomer contains no hydroxy functionality.
Claim 28
Dependent Claim
16 words
A polyhydroxy oligomer according to claim 25, wherein said alkyl hexahydrophthalic anhydride is methyl hexahydrophthalic anhydride.
Claim 29
Dependent Claim
14 words
A polyhydroxy oligomer according to claim 26, wherein said branched diol is 2-ethyl-1,3-hexane diol.
Claim 30
Dependent Claim
18 words
A polyhydroxy oligomer according to claim 27, wherein said monoepoxide C 2 -C 10 monomer is propylene oxide.
Claim 31
Dependent Claim
43 words
A polylhydroxy oligomer according to claim 19, wherein said acid ester is a dicarboxylic acid ester made by combining said diol and said anhydride in the reaction mixture in amounts and under conditions sufficient to result in reaction in a 1:2 molar ratio.
Claim 32
Dependent Claim
14 words
A polyhydroxy oligomer according to claim 29, wherein said branched diol is 2-ethyl-1,3-hexane diol.
Claim 33
Dependent Claim
14 words
A polyhydroxy oligomer according to claim 30, wherein said anhydride is methyl hexahydrophthalic anhydride.
Claim 34
Dependent Claim
26 words
A polyhydroxy oligomer according to claim 31, wherein said monomer is selected from the group consisting of alkylene monoepoxides, glycidyl esters, glycidyl ethers and mixtures thereof.
Claim 35
Dependent Claim
15 words
A polyhydroxy oligomer according to claim 32, wherein said monoepoxide monomer contains no hydroxyl functionality.
Claim 36
Dependent Claim
251 words
A high solids thermosetting coating composition which contains greater than about 60 percent by weight of nonvolatile solids, and which exclusive of pigments, solvents, and other nonreactive components consists essentially of: (A) a polyhydroxy oligomer having a number average (M n ) molecular weight of between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester; (B) an amine-aldehyde crosslinking agent; (C) 0-50 weight percent based on the total weight of (A), (B), (C) and (D) of a hydroxy functional additive having a number average molecular weight (M n ) of between about 150-6000; and (D) up to 15 weight percent based on the total weight of (A), (B), (C) and (D) of a flow control additive, said amine-aldehyde crosslinking agent being included in said composition in an amount sufficient to provide at least about 0.60 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxyl functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 37
Dependent Claim
251 words
A high solids thermosetting coating composition which contains greater than about 60 percent by weight of nonvolatile solids, and which exclusive of pigments, solvents, and other nonreactive components consists essentially of: (A) a polyhydroxy oligomer having a number average (M n ) molecular weight of between about 300-2000 and comprising the reaction product of: (i) an acid ester made by reacting: (a) a C 4 -C 10 aliphatic branched diol, and (b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and (ii) a monoepoxide C 2 -C 10 monomer, wherein said monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide group for each acid group of said acid ester; (B) an amine-aldehyde crosslinking agent; (C) 0-50 weight percent based on the total weight of (A), (B), (C) and (D) of a hydroxy functional additive having a number average molecular weight (M n ) of between about 150-6000; and (D) up to 15 weight percent based on the total weight of (A), (B), (C) and (D) of a flow control additive, said amine-aldehyde crosslinking agent being included in said composition in an amount sufficient to provide at least about 0.60 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxyl functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 38
Dependent Claim
23 words
A high solids coating composition according to claim 34, wherein the hydroxy groups of said diol are not attached to adjacent carbon atoms.
Claim 39
Dependent Claim
15 words
A high solids coating composition according to claim 35, wherein said diol is 2-ethyl-1,3-hexane diol.
Claim 40
Dependent Claim
29 words
A high solid coating composition according to claim 34, wherein the alkyl group of said alkyl hexahydropthalic anhydride comprises a lower alkyl group having up to about seven carbons.
Claim 41
Dependent Claim
18 words
A high solids coating composition according to claim 36 or 37, wherein said anhydride is methyl hexahydrophthalic anhydride.
Claim 42
Dependent Claim
33 words
A high solids coating composition according to claim 37, wherein said monoepoxide C 2 -C 10 monomer is selected from the group consisting of alkylene monoepoxides, glycidyl ethers, glycidyl esters, and mixtures thereof.
Claim 43
Dependent Claim
31 words
A high solids coating composition according to claims 34 or 39, wherein said polyhydroxy oligomer is a dihydroxy oligomer and said monoepoxide C 2 -C 10 monomer contains no hydroxyl functionality.
Claim 44
Dependent Claim
16 words
A high solids coating composition according to claim 40, wherein said monoepoxide monomer is propylene oxide.
Claim 45
Dependent Claim
82 words
A high solids coating composition according to claim 34, wherein said amine-aldehyded crosslinking agent is selected from the group consisting of condensation products of formaldehyde with melamine, substituted melamine, urea, benzoquanamine and substituted benzoquanamine, and mixtures of said condensation products in an amount sufficient to provide between about 0.75 and about 3.75 equivalents of nitrogen crosslinking functionality for each equivalent of hydroxy functionality included in said composition either on said polyhydroxy oligomer or as a hydroxyl group of said hydroxy functional additive.
Claim 46
Dependent Claim
81 words
A high solids coating composition according to claim 34, wherein said hydroxy functional additive is a polyol selected from the group consisting of (i) hydroxy functional polyester, (ii) hydroxy functional polyethers, (iii) hydroxy functional oligoesters, (iv) monomeric polyols, (v) hydroxy functional copolymers formed from monoethylenically usaturated monomers, one or more of which bears hydroxy functionality and which is included in said copolymer in amounts ranging from about 10 to about 50 weight percent of said copolymer, and (vi) mixtures of (i)-(v).
Claim 47
Dependent Claim
45 words
A high solids coating composition according to claim 34, wherein said acid ester is a dicarboxylic acid ester made by combining said diol and said anhydride in the reaction mixture in amounts and under conditions sufficient to result in reaction in a 1:2 molar ratio.
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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) | 1987-08-14 | 1988-02-13 | 1988-08-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-14 | 1992-02-13 | 1992-08-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-14 | 1996-02-13 | 1996-08-14 | $7700.00 | Window Closed / Lapsed |