Patent US4454265A successfully refreshed from Google Patents.
US4454265A
Expired / Lapsed
US
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Aqueous epoxy-phenolic coatings
Assignee: DeSoto Inc
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Filing: 1983-03-21
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Granted: 1984-06-12
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Expires: 2003-03-21
Abstract
Abstract Aqueous thermosetting coating compositions adapted for roll coat application are disclosed in which water has dispersed therein an adduct of a diglycidyl ether of a bisphenol having a 1,2-epoxy equivalency of at least 1.2 and an average molecular weight of from about 2000 to about 5000 with a stoichiometric proportion, based on epoxy and secondary amine, of diprimary amine having a single secondary amine group and each primary amine group blocked by a ketimine group. At least about 50% of the amine groups of this adduct are protonated with a volatile acid, and the ketimine groups hydrolyze in the water to provide primary amine functionality and ketone solvent in the aqueous medium. From 20% to 50%, based on total resin solids, of water insoluble, heat-hardening phenol-formaldehyde resin curing agent is employed for cure. The curing agents are added to the adduct in solution in water-miscible organic solvent, and cresol-formaldehyde curing agents are preferred.
Inventors
- 👤 Anthony J. Tortorello
- 👤 Donald R. Roberts
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:34
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4042; C09; C09D; C09D163/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
119 words
An aqueous coating composition adapted to thermoset on baking comprising, water having dispersed therein diglycidyl ether of a bisphenol having a 1,2-epoxy equivalency of at least 1.2 and an average molecular weight of from about 2000 to about 5000, adducted with a stoichiometric proportion, based on epoxy and secondary amine, of diprimary amine having a single secondary amine group and each primary amine group blocked by a ketimine group, at least about 50% of the amine groups of said adduct being protonated with a volatile acid, said ketimine groups being hydrolyzed in the aqueous medium to provide primary amine groups therein, and from 20% to 50%, based on total resin solids, of water insoluble, heat-hardening phenol-formaldehyde resin curing agent.
Claim 2
Dependent Claim
119 words
An aqueous coating composition adapted to thermoset on baking comprising, water having dispersed therein diglycidyl ether of a bisphenol having a 1,2-epoxy equivalency of at least 1.2 and an average molecular weight of from about 2000 to about 5000, adducted with a stoichiometric proportion, based on epoxy and secondary amine, of diprimary amine having a single secondary amine group and each primary amine group blocked by a ketimine group, at least about 50% of the amine groups of said adduct being protonated with a volatile acid, said ketimine groups being hydrolyzed in the aqueous medium to provide primary amine groups therein, and from 20% to 50%, based on total resin solids, of water insoluble, heat-hardening phenol-formaldehyde resin curing agent.
Claim 3
Dependent Claim
29 words
An aqueous coating composition as recited in claim 1 in which said diglycidyl ether is a derivative of bisphenol A having a 1,2-epoxy equivalency of from 1.6 to 2.0.
Claim 4
Dependent Claim
19 words
An aqueous coating composition as recited in claim 2 in which said ketimine-blocked diprimary amine is diketimine-blocked diethylene triamine.
Claim 5
Dependent Claim
20 words
An aqueous coating composition as recited in claim 3 in which said diethylene triamine is ketimine-blocked with methyl isobutyl ketone.
Claim 6
Dependent Claim
30 words
An aqueous coating composition as recited in claim 2 in which said phenol-formaldehyde resin curing agent is a cresol-formaldehyde resin containing about 1 mol of formaldehyde per mol of cresol.
Claim 7
Dependent Claim
15 words
An aqueous coating composition as recited in claim 5 in which said cresol is ortho-cresol.
Claim 8
Dependent Claim
20 words
An aqueous coating composition as recited in claim 5 in which said phenol-formaldehyde resin curing agent is a polymethylol phenol.
Claim 9
Dependent Claim
18 words
An aqueous coating composition as recited in claim 7 in which said polymethylol phenol is ammonia or amine-bridged.
Claim 10
Dependent Claim
23 words
An aqueous coating composition as recited in claim 1 in which said coating composition contains from 20% to 45% of total resin solids.
Claim 11
Dependent Claim
19 words
An aqueous coating composition as recited in claim 9 in which said coating composition is of roll coating viscosity.
Claim 12
Independent Claim
169 words
A method of providing an aqueous coating composition adapted to thermoset on baking comprising adducting a diglycidyl ether of a bisphenol having a 1,2-epoxy equivalency of at least 1.2 and an average molecular weight of from about 2000 to about 5000, with a stoichiometric proportion, based on epoxy and secondary amine, of diprimary amine having a single secondary amine group and each primary amine group blocked by a ketimine group, dissolving from 20% to 50%, based on total resin solids, of water insoluble, heat-hardening phenol-formaldehyde resin curing agent in said adduct in the presence of from 20% to 40% of water-miscible organic solvent, based on the weight of the solution, and dispersing said adduct-curing agent solution in water with at least about 50% of the amine groups of said adduct protonated with a volatile acid to stably disperse said adduct and said curing agent in the aqueous medium and to cause said ketimine groups to become hydrolyzed to provide primary amine groups and ketone solvent in the aqueous medium.
Claim 13
Independent Claim
169 words
A method of providing an aqueous coating composition adapted to thermoset on baking comprising adducting a diglycidyl ether of a bisphenol having a 1,2-epoxy equivalency of at least 1.2 and an average molecular weight of from about 2000 to about 5000, with a stoichiometric proportion, based on epoxy and secondary amine, of diprimary amine having a single secondary amine group and each primary amine group blocked by a ketimine group, dissolving from 20% to 50%, based on total resin solids, of water insoluble, heat-hardening phenol-formaldehyde resin curing agent in said adduct in the presence of from 20% to 40% of water-miscible organic solvent, based on the weight of the solution, and dispersing said adduct-curing agent solution in water with at least about 50% of the amine groups of said adduct protonated with a volatile acid to stably disperse said adduct and said curing agent in the aqueous medium and to cause said ketimine groups to become hydrolyzed to provide primary amine groups and ketone solvent in the aqueous medium.
Claim 14
Dependent Claim
44 words
A method as recited in claim 11 in which said diglycidyl ether is a derivative of bisphenol A having a 1,2-epoxy equivalency of from 1.6 to 2.0, and diethylene triamine which has been ketimine-blocked with methyl isobutyl ketone is adducted with said diglycidyl ether.
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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) | 1987-06-12 | 1987-12-12 | 1988-06-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-12 | 1991-12-12 | 1992-06-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-12 | 1995-12-12 | 1996-06-12 | $7700.00 | Window Closed / Lapsed |