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US4299747A Expired / Lapsed US ⏱️ 0.0 years remaining

Reaction products of a polyglycidyl ether of a polyphenol and an amino acid and aqueous solubilized products therefrom

Assignee: PPG Industries Inc
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Filing: 1977-03-08
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Granted: 1981-11-10
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Expires: 1997-03-08
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Abstract

Abstract Coating compositions which may be applied by conventional techniques as well as by electrodeposition are provided by reacting a polyglycidyl ether of a polyphenol with an amino acid containing at least one amine group and one carboxyl group, wherein the amine group of the acid is preferentially reactive with the epoxy groups of the polyglycidyl ether. The resultant product can then be solubilized by neutralizing at least a portion of the acid functionality thereof with an amine or other base. Especially useful amino acids are the aminobenzoic acids.

Inventors

  • 👤 William J. Birkmeyer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 10:40
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C08G59/52; C09; C09D; C09D163/00; Y; Y10; Y10S; Y10S524/00; Y10S524/901; Y10S525/00; Y10S525/917

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 70 words
A curable, carboxyl-containing precondensate prepared by reacting at a temperature from about 200° to about 350° F. (1) a polyglycidyl ether of a polyphenol with (2) an amino-substituted aromatic carboxylic acid selected from the class consisting of anthranilic acid, p-aminobenzoic acid, m-aminobenzoic acid, 3-amino-p-toluic acid, 3-amino-salicylic acid, 3-amino-4-methoxybenzoic acid, 6-amino-m-toluic acid, 3-amino-4-chlorobenzoic acid, 2-amino-5-nitrobenzoic acid, 2-nitro-5-aminobenzoic acid and 5-amino-isophthalic acid; said precondensate having an acid number of at least 15.
Claim 2
Dependent Claim 70 words
A curable, carboxyl-containing precondensate prepared by reacting at a temperature from about 200° to about 350° F. (1) a polyglycidyl ether of a polyphenol with (2) an amino-substituted aromatic carboxylic acid selected from the class consisting of anthranilic acid, p-aminobenzoic acid, m-aminobenzoic acid, 3-amino-p-toluic acid, 3-amino-salicylic acid, 3-amino-4-methoxybenzoic acid, 6-amino-m-toluic acid, 3-amino-4-chlorobenzoic acid, 2-amino-5-nitrobenzoic acid, 2-nitro-5-aminobenzoic acid and 5-amino-isophthalic acid; said precondensate having an acid number of at least 15.
Claim 3
Dependent Claim 18 words
The precondensate of claim 1 wherein the polyglycidyl ether of a polyphenol is a glycidyl polyether of 2,2-bis(4-hydroxyphenyl)propane.
Claim 4
Dependent Claim 25 words
The precondensate of claim 1 wherein the amino-substituted aromatic carboxylic acid is selected from the class consisting of anthranilic acid, p-aminobenzoic acid and m-aminobenzoic acid.
Claim 5
Dependent Claim 14 words
The precondensate of claim 3 wherein the amino-substituted aromatic carboxylic acid is p-aminobenzoic acid.
Claim 6
Dependent Claim 12 words
A curable composition comprising the polycondensate of claim 1 and a polyamide.
Claim 7
Dependent Claim 87 words
An anionic aqueous composition comprising water and an at least partially base neutralized reaction product of: (a) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency greater than 1.0; and (b) an aromatic amino acid selected from the class consisting of an anthranilic acid, p-amino benzoic acid, m-amino benzoic acid, 3-amino-p-toluic acid, 3-amino-4-methoxy benzoic acid, 6-amino-m-toluic acid, 3-amino-4-chloro-benzoic acid, 2-amino-5-nitro benzoic acid, 2-nitro-5-amino benzoic acid, 5-amino isophthalic acid; said reaction product having unreacted carboxylic acid groups which are neutralized with base to form anionic salt groups.
Claim 8
Dependent Claim 87 words
An anionic aqueous composition comprising water and an at least partially base neutralized reaction product of: (a) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency greater than 1.0; and (b) an aromatic amino acid selected from the class consisting of an anthranilic acid, p-amino benzoic acid, m-amino benzoic acid, 3-amino-p-toluic acid, 3-amino-4-methoxy benzoic acid, 6-amino-m-toluic acid, 3-amino-4-chloro-benzoic acid, 2-amino-5-nitro benzoic acid, 2-nitro-5-amino benzoic acid, 5-amino isophthalic acid; said reaction product having unreacted carboxylic acid groups which are neutralized with base to form anionic salt groups.
Claim 9
Dependent Claim 29 words
The aqueous composition of claim 6 wherein the equivalent ratio of epoxy groups in said polyglycidyl ether to amine groups in said amino acid is between 1:0.20 and 1:1.25.
Claim 10
Dependent Claim 19 words
The aqueous composition of claim 6 wherein said reaction product is at least partially neutralized with a volatile base.
Claim 11
Dependent Claim 12 words
The aqueous composition of claim 8 wherein said base is an amine.
Claim 12
Dependent Claim 12 words
The aqueous composition of claim 6 wherein said polyphenol is bisphenol A.
Claim 13
Dependent Claim 13 words
The aqueous composition of claim 6 wherein said amino acid is anthranilic acid.
Claim 14
Dependent Claim 13 words
The aqueous composition of claim 6 wherein said amino acid is p-aminobenzoic acid.
Claim 15
Dependent Claim 13 words
The aqueous composition of claim 6 wherein said amino acid is m-aminobenzoic acid.
Claim 16
Dependent Claim 116 words
An anionic aqueous composition comprising water and: (a) an at least partially base neutralized reaction product of: (1) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency of greater than 1.0; and (2) an aromatic amino acid selected from the class consisting of an anthranilic acid, p-amino benzoic acid, m-amino benzoic acid, 3-amino-p-toluic acid, 3-amino-4-methoxy benzoic acid, 6-amino-m-toluic acid, 3-amino-4-chloro-benzoic acid, 2-amino-5-nitro benzoic acid, 2-nitro-5-amino benzoic acid, 5-amino isophthalic acid; said reaction product having unreacted carboxylic acid groups which are neutralizable with base to form anionic salt groups; and (b) a resin selected from the group consisting of hydrocarbon resins, water-soluble acrylic resins, acrylic polymer emulsions, aqueous dispersions of amide-containing acrylic interpolymers, or combinations thereof.
Claim 17
Dependent Claim 116 words
An anionic aqueous composition comprising water and: (a) an at least partially base neutralized reaction product of: (1) a polyglycidyl ether of a polyphenol having a 1,2-epoxy equivalency of greater than 1.0; and (2) an aromatic amino acid selected from the class consisting of an anthranilic acid, p-amino benzoic acid, m-amino benzoic acid, 3-amino-p-toluic acid, 3-amino-4-methoxy benzoic acid, 6-amino-m-toluic acid, 3-amino-4-chloro-benzoic acid, 2-amino-5-nitro benzoic acid, 2-nitro-5-amino benzoic acid, 5-amino isophthalic acid; said reaction product having unreacted carboxylic acid groups which are neutralizable with base to form anionic salt groups; and (b) a resin selected from the group consisting of hydrocarbon resins, water-soluble acrylic resins, acrylic polymer emulsions, aqueous dispersions of amide-containing acrylic interpolymers, or combinations thereof.
Claim 18
Dependent Claim 11 words
The aqueous composition of claim 14 further containing a curing agent.
Claim 19
Dependent Claim 41 words
The aqueous composition of claim 14 wherein said composition based on total weight of (a) and (b) contains from about 5 to about 95 percent by weight of (a) and from about 95 to about 5 percent by weight of (b).
Claim 20
Dependent Claim 14 words
The aqueous composition of claim 14 wherein said resin is an acrylic polymer emulsion.
Claim 21
Dependent Claim 18 words
The aqueous composition of claim 14 wherein said resin is an aqueous dispersion of an amide-containing acrylic interpolymer.
Claim 22
Dependent Claim 12 words
The aqueous composition of claim 14 further containing a pigment or pigments.

References Cited (Backward Citations)

US3479310A Cited
GB1204862A Cited
US3839252A Cited
US3928156A Cited
US3945952A Cited
GB1448134A Cited
US4119609A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-11-09 1985-05-11 1985-11-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-11-09 1989-05-11 1989-11-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-11-09 1993-05-11 1993-11-10 $7700.00 Window Closed / Lapsed

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