US4568709A
Expired / Lapsed
US
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Cathodically depositable electrodeposition paint binders based on reaction products of epoxy resin-amino adduct with formaldehyde and phenols
Assignee: Allnex Austria GmbH
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Filing: 1985-03-18
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Granted: 1986-02-04
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Expires: 2005-03-18
Abstract
Abstract Cathodically depositable electrodeposition paint binders comprising the reaction product of an epoxy resin with at least two epoxy groups with amines carrying primary amino groups and, optionally, with a carboxylic acid compound to provide an epoxy resin-amino adduct which is then reacted with a phenol and formaldehyde. The binders have excellent corrosion resistance and crosslink to provide coating films at relatively low stoving temperatures without splitting off of substances harmful to the environment.
Inventors
- 👤 Willibald Paar
- 👤 Johann Gmoser
- 👤 Helmut Honig
- 👤 Wolfgang Daimer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:30
CPC Classifications
C; C09; C09D; C09D5/00; C09D5/44; C09D5/4419; C08; C08G; C08G14/00; C08G14/14; Y; Y10; Y10S; Y10S524/00; Y10S524/901
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
164 words
Process for producing cathodically depositable electrodeposition paint binders based on modified epoxy resins characterized in that an epoxy resin with at least two epoxy groups and having an epoxy equivalent weight of from about 180 to 1000 is reacted at from about 50° to 120° C. with 0.6 to 1.0 moles of primary amino groups on a primary monoalkyl amine or a primary alkylene diamine or a primary-tertiary alkylene diamine per each available epoxy group and 0 to 0.4 moles of a carboxylic compound or a secondary amine per each available epoxy group to provide an epoxy resin-amino adduct having an epoxy value of substantially zero, said epoxy resin-amino adduct thereafter being reacted at from about 50° to 90° C., calculated on one mole of NH-groups, with 0.5 to 1.0 moles phenol, and with 0.25 to 0.9 moles of formaldehyde per formaldehyde-reactive site, until the formaldehyde is substantially bound and the reaction product, upon partial or total neutralization with acids, is dilutable with water.
Claim 2
Dependent Claim
164 words
Process for producing cathodically depositable electrodeposition paint binders based on modified epoxy resins characterized in that an epoxy resin with at least two epoxy groups and having an epoxy equivalent weight of from about 180 to 1000 is reacted at from about 50° to 120° C. with 0.6 to 1.0 moles of primary amino groups on a primary monoalkyl amine or a primary alkylene diamine or a primary-tertiary alkylene diamine per each available epoxy group and 0 to 0.4 moles of a carboxylic compound or a secondary amine per each available epoxy group to provide an epoxy resin-amino adduct having an epoxy value of substantially zero, said epoxy resin-amino adduct thereafter being reacted at from about 50° to 90° C., calculated on one mole of NH-groups, with 0.5 to 1.0 moles phenol, and with 0.25 to 0.9 moles of formaldehyde per formaldehyde-reactive site, until the formaldehyde is substantially bound and the reaction product, upon partial or total neutralization with acids, is dilutable with water.
Claim 3
Dependent Claim
16 words
The process according to claim 1 wherein the said phenol is a mono- or polynuclear phenol.
Claim 4
Dependent Claim
18 words
The process according to claim 2 wherein said mono- or polynuclear phenol is substituted with an alkyl group.
Claim 5
Dependent Claim
19 words
The process according to claim 2 wherein the amine is a primary monoalkylamine with at least four carbon atoms.
Claim 6
Dependent Claim
19 words
The process according to claim 1 wherein said phenol is an amino-alkylation product of a monosubstituted or dinuclear phenol.
Claim 7
Dependent Claim
18 words
The process according to claim 1 wherein a portion of said phenol is substituted with a formaldehyde-reactive compound.
Claim 8
Dependent Claim
15 words
The process according to claim 6 wherein said formaldehyde-reactive compound is urea, melamine, or guanamine.
Claim 9
Dependent Claim
22 words
The process according to claim 7 wherein the carboxylic compound is a monocarboxylic acid which has from 7 to 20 carbon atoms.
Claim 10
Dependent Claim
23 words
The process according to claim 7 wherein the carboxylic compound is a semiester of a dicarboxylic acid with monoalcohols or an oxazolidine compound.
Claim 11
Dependent Claim
19 words
The process according to claim 1 wherein the epoxy resin is based on bisphenol A or a phenol novolak.
Claim 12
Dependent Claim
19 words
The process according to claim 1 wherein the amine is a blend of primary monoalkylamines and primary alkylene diamines.
Claim 13
Dependent Claim
24 words
The process according to claim 1 wherein the reaction of the epoxy groups with the amines is carried out at 50° to 90° C.
Claim 14
Dependent Claim
26 words
The process according to claim 1 wherein the reaction of the epoxy groups with the carboxylic compounds is carried out at from 90° to 120° C.
Claim 15
Dependent Claim
59 words
The process according to claim 13 wherein the carboxylic compound is an addition product of maleic acid anhydride to an unsaturated oil or the hydroxy-free esters of an oil fatty acid with a polyol or a low molecular unsaturated hydrocarbon polymer or oligomer, the anhydride groups of maleic acid having been opened through semiester formation with a monohydroxy compound.
Claim 16
Dependent Claim
21 words
The process according to claim 14 wherein the carboxylic compounds have an acid value of from 30 to 130 mg KOH/g.
Claim 17
Dependent Claim
22 words
The process according to claim 15 wherein the number of carboxy groups of the semiesters is reduced through reaction with monoepoxy compounds.
Claim 18
Dependent Claim
42 words
The process according to claim 1 wherein an auxiliary organic solvent is utilized in the process and, after neutralization with acids and dilution with water, the solvent is at least partly vacuum-stripped from the reaction product at from 30° to 60° C.
Claim 19
Dependent Claim
161 words
Cathodically depositable electrodeposition paint binders based on modified epoxy resins comprising the reaction product at from about 50° to 120° C. of an epoxy resin with at least two epoxy groups and an epoxy equivalent weight of from about 180 to 1000 with 0.6 to 1.0 moles of primary amino groups on a primary monoalkyl or a primary alkylene diamine or a primary-tertiary alkylene diamine per each available epoxy group and 0 to 0.4 moles of a carboxylic compound or a secondary amine per each available epoxy group to provide an epoxy resin-amino adduct having an epoxy value of substantially zero, said epoxy resin-amino adduct thereafter reacted at from about 50° to 90° C. per mole of NH-groups, with 0.5 to 1.0 moles of a phenol and 0.25 to 0.9 moles of formaldehyde per formaldehyde-reactive site to provide a product wherein said formaldehyde is substantially bound and said reaction product, upon partial or total neutralization with acids, is dilutable with water.
Claim 20
Dependent Claim
161 words
Cathodically depositable electrodeposition paint binders based on modified epoxy resins comprising the reaction product at from about 50° to 120° C. of an epoxy resin with at least two epoxy groups and an epoxy equivalent weight of from about 180 to 1000 with 0.6 to 1.0 moles of primary amino groups on a primary monoalkyl or a primary alkylene diamine or a primary-tertiary alkylene diamine per each available epoxy group and 0 to 0.4 moles of a carboxylic compound or a secondary amine per each available epoxy group to provide an epoxy resin-amino adduct having an epoxy value of substantially zero, said epoxy resin-amino adduct thereafter reacted at from about 50° to 90° C. per mole of NH-groups, with 0.5 to 1.0 moles of a phenol and 0.25 to 0.9 moles of formaldehyde per formaldehyde-reactive site to provide a product wherein said formaldehyde is substantially bound and said reaction product, upon partial or total neutralization with acids, is dilutable with water.
Claim 21
Dependent Claim
16 words
The binder according to claim 18 wherein the said phenol is a mono- or polynuclear phenol.
Claim 22
Dependent Claim
18 words
The binder according to claim 19 wherein said mono- or polynuclear phenol is substituted with an alkyl group.
Claim 23
Dependent Claim
19 words
The binder according to claim 19 wherein the amine is a primary monoalkylamine with at least four carbon atoms.
Claim 24
Dependent Claim
19 words
The binder according to claim 18 wherein said phenol is an amino-alkylation product of a monosubstituted or dinuclear phenol.
Claim 25
Dependent Claim
18 words
The binder according to claim 18 wherein a portion of said phenol is substituted with a formaldehyde-reactive compound.
Claim 26
Dependent Claim
19 words
The binder according to claim 18 wherein the epoxy resin is based on bisphenol A or a phenol novolak.
Claim 27
Dependent Claim
19 words
The binder according to claim 18 wherein the amine is a blend of primary monoalkylamines and primary alkylene diamines.
Claim 28
Dependent Claim
22 words
The binder according to claim 18 wherein the carboxylic compound is a monocarboxylic acid which has from 7 to 20 carbon atoms.
Claim 29
Dependent Claim
59 words
The binder according to claim 26 wherein the carboxylic compound is an addition product of maleic acid anhydride to an unsaturated oil or the hydroxy-free esters of an oil fatty acid with a polyol or a low molecular unsaturated hydrocarbon polymer or oligomer, the anhydride groups of maleic acid having been opened through semiester formation with a monohydroxy compound.
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) | 1989-02-03 | 1989-08-05 | 1990-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-03 | 1993-08-05 | 1994-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-03 | 1997-08-05 | 1998-02-04 | $7700.00 | Window Closed / Lapsed |