Patent US3960795A successfully refreshed from Google Patents.
US3960795A
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Hydrolyzed reaction product of a polyepoxide with a phenolic compound having a group hydrolyzable to carboxyl
Assignee: PPG Industries Inc
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Filing: 1974-08-13
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Granted: 1976-06-01
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Expires: 1994-08-13
Abstract
Abstract Coating compositions applicable by conventional coating techniques as well as by electrodeposition are provided by reacting an epoxy-containing organic material with a compound containing at least one phenolic hydroxyl group and a group hydrolyzable to a carboxyl group. Examples of such hydrolyzable groups include ester groups, amide groups and nitrile groups. Compounds include esters of benzoic, salicylic and diphenolic acids, and phenolphthalein. The resultant product may then be hydrolyzed and solubilized, using any of the known hydrolyzing agents, e.g., aqueous potassium hydroxide, aqueous sodium hydroxide and aqueous solutions of the various amines used in the art.
Inventors
- 👤 Rostyslaw Dowbenko
- 👤 Joseph R. Marchetti
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:34
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/62; C08G59/625; C09; C09D; C09D5/00; C09D5/44; C09D5/4419; C09D5/4423; C09D5/4426; Y; Y10; Y10S; Y10S524/00; Y10S524/901
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
153 words
A solubilized aqueous composition formed from reacting and then subsequently hydrolyzing A. a polyepoxide having an epoxy equivalency greater than 1.0; and B. a compound containing at least one phenolic hydroxyl group and containing at least one group hydrolyzable to a carboxyl group and having the following structural formula: (HO).sub.n R--W).sub.m wherein n and m are integers of at least 1 and preferably 1 to 4, wherein R is an organic radical containing at least one aryl group, and wherein at least one of the hydroxyl groups is attached to at least one of the aryl groups of R; W is a group hydrolyzable to a carboxyl group selected from the group consisting of --COOR', --CON(R") 2 and --CN, where R' is a lower alkyl group of from 1 to 4 carbon atoms, and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof or wherein (B) is phenolphthalein.
Claim 2
Dependent Claim
153 words
A solubilized aqueous composition formed from reacting and then subsequently hydrolyzing A. a polyepoxide having an epoxy equivalency greater than 1.0; and B. a compound containing at least one phenolic hydroxyl group and containing at least one group hydrolyzable to a carboxyl group and having the following structural formula: (HO).sub.n R--W).sub.m wherein n and m are integers of at least 1 and preferably 1 to 4, wherein R is an organic radical containing at least one aryl group, and wherein at least one of the hydroxyl groups is attached to at least one of the aryl groups of R; W is a group hydrolyzable to a carboxyl group selected from the group consisting of --COOR', --CON(R") 2 and --CN, where R' is a lower alkyl group of from 1 to 4 carbon atoms, and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof or wherein (B) is phenolphthalein.
Claim 3
Dependent Claim
17 words
The aqueous composition of claim 1, wherein said compound is an alkyl ester of hydroxy benzoic acid.
Claim 4
Dependent Claim
18 words
The aqueous composition of claim 2, wherein said alkyl ester of hydroxy benzoic acid is methyl p-hydroxy benzoate.
Claim 5
Dependent Claim
17 words
The aqueous composition of claim 2, wherein said alkyl ester of hydroxy benzoic acid is methyl salicylate.
Claim 6
Dependent Claim
16 words
The aqueous composition of claim 1, wherein said compound is an alkyl ester of 4,4-bis(p-hydroxyphenyl)pentanoic acid.
Claim 7
Dependent Claim
12 words
The aqueous composition of claim 1 wherein said compound is phenol phthalein.
Claim 8
Dependent Claim
30 words
The aqueous composition of claim 1 wherein the equivalent ratio of epoxy groups in the epoxy-containing organic material to hydroxyl groups in said compound is between about 1:0.25 and 1:1.25.
Claim 9
Dependent Claim
16 words
The aqueous composition of claim 7 wherein said equivalent ratio is between about 1:0.5 and 1:1.
Claim 10
Independent Claim
158 words
A method of preparing an aqueous composition comprising: A. reacting a polyepoxide having a 1,2-epoxy equivalency greater than 1.0 with a compound containing at least one phenolic hydroxyl group and containing at least one group hydrolyzable to a carboxyl group having the following structural formula: (HO).sub.n R--W).sub.m wherein n and m are integers of at least 1 and preferably 1 to 4, wherein R is an organic radical containing at least one aryl group, and wherein at least one of the hydroxyl groups is attached to at least one of the aryl groups of R; W is a group hydrolyzable to a carboxyl group selected from the group consisting of --COOR', --CON(R") 2 and --CN, where R' is a lower alkyl group of from 1 to 4 carbon atoms, and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof or wherein the compound is phenolphthalein; and B. hydrolyzing and solubilizing the resultant product.
Claim 11
Independent Claim
158 words
A method of preparing an aqueous composition comprising: A. reacting a polyepoxide having a 1,2-epoxy equivalency greater than 1.0 with a compound containing at least one phenolic hydroxyl group and containing at least one group hydrolyzable to a carboxyl group having the following structural formula: (HO).sub.n R--W).sub.m wherein n and m are integers of at least 1 and preferably 1 to 4, wherein R is an organic radical containing at least one aryl group, and wherein at least one of the hydroxyl groups is attached to at least one of the aryl groups of R; W is a group hydrolyzable to a carboxyl group selected from the group consisting of --COOR', --CON(R") 2 and --CN, where R' is a lower alkyl group of from 1 to 4 carbon atoms, and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof or wherein the compound is phenolphthalein; and B. hydrolyzing and solubilizing the resultant product.
Claim 12
Dependent Claim
29 words
The method of claim 9 wherein the equivalent ratio of epoxy groups in the epoxy-containing organic material to hydroxyl groups in said compound is between about 1:0.25 and 1:1.25.
Claim 13
Dependent Claim
15 words
The method of claim 10 wherein said equivalent ratio is between about 1:0.5 and 1:1.
Claim 14
Dependent Claim
16 words
The method of claim 9 wherein said compound is an alkyl ester of hydroxy benzoic acid.
Claim 15
Dependent Claim
26 words
The method of claim 12 wherein said alkyl ester of hydroxy benzoic acid is selected from the group consisting of methyl p-hydroxy benzoate and methyl salicylate.
Claim 16
Dependent Claim
16 words
The method of claim 9 wherein said compound is an alkyl ester of 4,4-bis(p-hydroxy phenyl)pentanoic acid.
Claim 17
Dependent Claim
28 words
The method of claim 9 wherein said reaction product is solubilized with a member selected from the group consisting of metal hydroxides, ammonia, amines and quaternary ammonium compounds.
Claim 18
Dependent Claim
17 words
The method of claim 15 wherein said reaction product is solubilized with an aqueous metal hydroxide solution.
Claim 19
Dependent Claim
12 words
The method of claim 16 wherein said metal hydroxide is potassium hydroxide.
Claim 20
Dependent Claim
36 words
The method of claim 16 further comprising the steps of C. reacting an acid with the solubilized reaction product; D. filtering off the resultant salt formed; and E. reacting the filtrate with an aqueous amine solution.
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) | 1979-06-01 | 1979-12-01 | 1980-06-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-01 | 1983-12-01 | 1984-06-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-01 | 1987-12-01 | 1988-06-01 | $7700.00 | Window Closed / Lapsed |