US4174333A
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Carboxylated amide polymers and coating compositions containing same
Assignee: PPG Industries Inc
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Filing: 1978-11-02
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Granted: 1979-11-13
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Expires: 1998-11-02
Abstract
Abstract Carboxylated amide polymers and coating compositions containing same are especially useful for the coating of food and beverage containers. The carboxylated amide polymers are the reaction product of (1) a compound of formula: ##STR1## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 or R 4 is hydrogen, and n is at least 1.0 with (2) a cyclic anhydride of a dibasic carboxylic acid. The carboxylated amide polymers can be made water reducible by neutralizing the polymer with an organic or inorganic base and used in aqueous coating compositions.
Inventors
- 👤 Marvis E. Hartman
- 👤 Thomas R. Hockswender
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 16:54
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C08G59/56; C08G59/58; C08G69/00
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
120 words
A carboxylated amide polymer, said polymer being the reaction product of (1) a compound having the formula ##STR6## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 group is hydrogen and n is greater than 1.0 with (2) a cyclic anhydride of a dicarboxylic acid.
Claim 2
Dependent Claim
120 words
A carboxylated amide polymer, said polymer being the reaction product of (1) a compound having the formula ##STR6## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 group is hydrogen and n is greater than 1.0 with (2) a cyclic anhydride of a dicarboxylic acid.
Claim 3
Dependent Claim
15 words
The carboxylated amide polymer of claim 1 wherein x is 0 and y is 1.
Claim 4
Dependent Claim
11 words
The carboxylated amide polymer of claim 1 wherein y is 0.
Claim 5
Dependent Claim
18 words
The carboxylated amide polymer of claim 1 wherein x is 1 and y is from 1 to 4.
Claim 6
Dependent Claim
14 words
The carboxylated amide polymer of claims 2 or 4 wherein R 1 is hydrogen.
Claim 7
Dependent Claim
21 words
The carboxylated amide polymer of claims 2, 3 or 4 wherein R 1 , R 3 and R 4 are hydrogens.
Claim 8
Dependent Claim
16 words
The carboxylated amide polymer of claim 3 wherein R 3 is a C 1-6 alkyl group.
Claim 9
Dependent Claim
18 words
The carboxylated amide polymer of claim 6 wherein the cyclic anhydride has from 4 to 14 carbon atoms.
Claim 10
Dependent Claim
14 words
The carboxylated amide polymer of claim 8 wherein the cyclic anhydride is succinic anhydride.
Claim 11
Dependent Claim
18 words
The carboxylated amide polymer of claim 1 wherein A is derived from a polyglycidyl ether of a polyphenol.
Claim 12
Dependent Claim
20 words
The carboxylated amide polymer of claim 1 wherein A is derived from an addition polymerized polymer containing pendent epoxy groups.
Claim 13
Dependent Claim
17 words
The carboxylated amide polymer of claim 11 wherein A is derived from a glycidyl acrylate or methacrylate.
Claim 14
Dependent Claim
150 words
A process of making carboxylated amide polymers, comprising the steps of: (a) reacting a polyepoxide resin with ammonia or an amine having at least two active hydrogen atoms to obtain compounds of the formula: ##STR7## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on the polyepoxide with the ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 is hydrogen and n is greater than 1.0; and (b) reacting the product of step (a) with a cyclic anhydride of a dicarboxylic acid to obtain the carboxylated amide polymer.
Claim 15
Dependent Claim
150 words
A process of making carboxylated amide polymers, comprising the steps of: (a) reacting a polyepoxide resin with ammonia or an amine having at least two active hydrogen atoms to obtain compounds of the formula: ##STR7## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on the polyepoxide with the ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 is hydrogen and n is greater than 1.0; and (b) reacting the product of step (a) with a cyclic anhydride of a dicarboxylic acid to obtain the carboxylated amide polymer.
Claim 16
Dependent Claim
27 words
The process of claim 13 wherein a molar excess of ammonia or amine of up to about 10:1 is used in the reaction with the polyepoxide resin.
Claim 17
Dependent Claim
13 words
The process of claim 14 wherein ammonia is reacted with the polyepoxide resin.
Claim 18
Dependent Claim
15 words
The process of claim 14 wherein a primary amine is reacted with the polyepoxide resin.
Claim 19
Dependent Claim
16 words
The process of claim 14 wherein a di- or polyamine is reacted with the polyepoxide resin.
Claim 20
Dependent Claim
19 words
The process or claims 15, 16 or 17 wherein A is derived from a polyglycidyl ether of a polyphenol.
Claim 21
Dependent Claim
21 words
The process of claims 15, 16 or 17 wherein A is derived from an addition polymerized polymer having pendent epoxy groups.
Claim 22
Dependent Claim
19 words
The process of claims 15, 16 or 17 wherein the cyclic anhydride has from 4 to 14 carbon atoms.
Claim 23
Dependent Claim
16 words
The process of claim 20 wherein the product of step (a) is reacted with succinic anhydride.
Claim 24
Dependent Claim
39 words
The process of claims 15, 16 or 17 additionally comprising the step of reacting the product of step (b) with an organic or inorganic basic compound to partially neutralize or neutralize the polymer to impart water-reducibility to the polymers.
Claim 25
Dependent Claim
153 words
A coating composition consisting essentially of, on a solids basis; (a) from about 25 percent to about 99 percent of a carboxylated amide polymer, said polymer being the reaction product of (1) compounds having the formula ##STR8## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, and R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 is hydrogen and n is at least 1.0 with (2) a cyclic anhydride of a dicarboxylic acid; and (b) from about 1 percent to about 75 percent of a crosslinking agent.
Claim 26
Dependent Claim
153 words
A coating composition consisting essentially of, on a solids basis; (a) from about 25 percent to about 99 percent of a carboxylated amide polymer, said polymer being the reaction product of (1) compounds having the formula ##STR8## wherein A is the organic residue resulting from a ring opening reaction of a 1,2-epoxy group on a polyepoxide with ammonia or amine, R 1 is hydrogen or a C 1-4 alkyl group, R 2 is a C 2-12 alkylene group, x is 0 or 1, y is from 0 to 4, R 3 is hydrogen or a C 1-6 alkyl group, and R 4 is hydrogen or a C 1-6 alkyl group, provided at least one R 1 , R 3 and R 4 is hydrogen and n is at least 1.0 with (2) a cyclic anhydride of a dicarboxylic acid; and (b) from about 1 percent to about 75 percent of a crosslinking agent.
Claim 27
Dependent Claim
40 words
The coating composition of claim 23 wherein the resin is neutralized with an organic or inorganic base to impart water reducibility to the resin and the composition additionally consists essentially of water or a mixture of water and organic solvent.
Claim 28
Dependent Claim
14 words
The coating composition of claim 24 wherein x is 0 and y is 1.
Claim 29
Dependent Claim
10 words
The coating composition of claim 24 wherein y is 0.
Claim 30
Dependent Claim
17 words
The coating composition of claim 24 wherein x is 1 and y is from 1 to 4.
Claim 31
Dependent Claim
13 words
The coating composition of claims 25 or 27 wherein R 1 is hydrogen.
Claim 32
Dependent Claim
20 words
The coating composition of claims 25, 26 or 27 wherein R 1 , R 3 and R 4 are hydrogens.
Claim 33
Dependent Claim
15 words
The coating composition of claim 26 wherein R 3 is a C 1-6 alkyl group.
Claim 34
Dependent Claim
17 words
The coating composition of claim 29 wherein the cyclic anhydride has from 4 to 14 carbon atoms.
Claim 35
Dependent Claim
17 words
The coating composition of claim 23 wherein A is derived from a polyglycidyl ether of a polyphenol.
Claim 36
Dependent Claim
19 words
The coating composition of claim 23 wherein A is derived from an addition polymerized polymer containing pendent epoxy groups.
Claim 37
Dependent Claim
17 words
The coating composition of claim 33 wherein the polymer is derived from a glycidyl acrylate or methacrylate.
Claim 38
Dependent Claim
29 words
The coating composition of claim 24 wherein the cross-linking agent is selected from the group consisting of an aminoplast resin, phenolic resin, blocked or semi-blocked polyisocyanate, and mixtures thereof.
Claim 39
Dependent Claim
15 words
The coating composition of claim 35 wherein the crosslinking agent is an etherified melamine-formaldehyde resin.
Claim 40
Dependent Claim
47 words
The coating composition of claim 35 wherein the carboxylated amide polymer is present at a level of from about 75 percent to about 99 percent and the crosslinking agent is present at a level of from about 1 percent to about 25 percent, on a solids basis.
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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) | 1982-11-12 | 1983-05-14 | 1983-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-12 | 1987-05-14 | 1987-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-12 | 1991-05-14 | 1991-11-13 | $7700.00 | Window Closed / Lapsed |