US4029621A
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Reaction products of a polyepoxide with a thiol having a group hydroyzable to carboxyl, and aqueous solubilized products
Assignee: PPG Industries Inc
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Filing: 1976-04-28
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Granted: 1977-06-14
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Expires: 1996-04-28
Abstract
Abstract Aqueous coating compositions which may be applied by conventional coating techniques as well as by electrodeposition are provided by reacting an epoxy-containing organic material with a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group. Examples of such hydrolyzable groups include ester groups, amide groups and nitrile groups. The resultant product is then hydrolyzed and solubilized using hydrolyzing agents such as aqueous alkali metal hydroxides and aqueous solutions of various amines.
Inventors
- 👤 Marvis E. Hartman
- 👤 Thomas R. Hockswender
- 👤 Rostyslaw Dowbenko
- 👤 Roger M. Christenson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:09
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/66; C08G59/14; C08G59/1433; C08G59/1483; C08G59/42; C08G59/4207
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
75 words
An aqueous composition comprising the solubilized reaction product of: A. a polyepoxide containing a 1,2-epoxy equivalency greater then 1.0; and B. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group.
Claim 2
Dependent Claim
75 words
An aqueous composition comprising the solubilized reaction product of: A. a polyepoxide containing a 1,2-epoxy equivalency greater then 1.0; and B. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group.
Claim 3
Dependent Claim
27 words
The aqueous composition of claim 1, wherein the equivalent ratio of epoxy groups in the polyepoxide to mercaptan groups in said compound is between 1:0.25 and 1:1.25.
Claim 4
Dependent Claim
15 words
The aqeuous composition of claim 2, wherein said equivalent ratio is between 1:0.5 and 1:1.
Claim 5
Dependent Claim
49 words
The aqueous composition of claim 1, wherein W is selected from the group consisting of --COOR', --CON(R") 2 , and --CN, where R' is an alkyl group of from 1 to 10 carbon atoms and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof.
Claim 6
Dependent Claim
16 words
The aqueous composition of claim 1, wherein said compound is an alkyl ester of mercaptoacetic acid.
Claim 7
Dependent Claim
19 words
The aqueous composition of claim 1, wherein said compound is an alkyl ester of α-mercaptopropionic acid or β-mercaptopropionic acid.
Claim 8
Dependent Claim
19 words
The aqueous composition of claim 1, wherein said compound is ethyl thioglycolate, n-butyl thioglycolate, isooctyl thioglycolate or isooctyl mercaptoproprionate.
Claim 9
Dependent Claim
18 words
The aqueous composition of claim 1, further comprising an active-hydrogen containing material having an average functionality of 2.
Claim 10
Dependent Claim
74 words
An aqueous composition comprising the solubilized reaction product of: A. a polyepoxide having a 1,2-epoxy equivalency greater than 1.0; and B. a compound containing a mercaptan group and an ester group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(COOR').sub.m wherein m is 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and R' is an alkyl group having from 1 to 10 carbon atoms.
Claim 11
Dependent Claim
74 words
An aqueous composition comprising the solubilized reaction product of: A. a polyepoxide having a 1,2-epoxy equivalency greater than 1.0; and B. a compound containing a mercaptan group and an ester group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(COOR').sub.m wherein m is 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and R' is an alkyl group having from 1 to 10 carbon atoms.
Claim 12
Dependent Claim
27 words
The aqueous composition of claim 9, wherein the equivalent ratio of epoxy groups in the polyepoxide to mercaptan groups in said compound is between 1:0.25 and 1:1.25.
Claim 13
Dependent Claim
19 words
The aqueous composition of claim 9, wherein said compound is ethyl thioglycolate, n-butyl thioglycolate, isooctyl thioglycolate or isooctyl mercaptopropionate.
Claim 14
Independent Claim
80 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 a mercapto group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1to 5, R is an organic radical having from 1 to 10 carbon atoms and wherein W is a group hydrolyzable to a carboxyl group; and B. solubilizing the reaction product.
Claim 15
Independent Claim
80 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 a mercapto group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1to 5, R is an organic radical having from 1 to 10 carbon atoms and wherein W is a group hydrolyzable to a carboxyl group; and B. solubilizing the reaction product.
Claim 16
Dependent Claim
27 words
The method of claim 12, wherein the equivalent ratio of 1,2-epoxy groups in the polyepoxide to mercaptan groups in said compound is between about 1:0.25 and 1:1.25.
Claim 17
Dependent Claim
48 words
The method of claim 12, wherein W is selected from the group consisting of --COOR', --CON(R") 2 , and --CN, where R' is an alkyl group of from 1 to 10 carbon atoms and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof.
Claim 18
Dependent Claim
15 words
The method of claim 12, wherein said compound is an alkyl ester of mercaptoacetic acid.
Claim 19
Dependent Claim
18 words
The method of claim 12, wherein said compound is an alkyl ester of α-mercaptopropionic acid or β-mercaptopropionic acid.
Claim 20
Dependent Claim
18 words
The method of claim 12, wherein said compound is n-butyl thioglycolate, ethyl thioglycolate, isooctyl thioglycolate or isooctyl mercaptopropionate.
Claim 21
Dependent Claim
34 words
The method of claim 12, wherein said reaction product is solubilized with an aqueous solution of a basic compound selected from the group consisting of alkali metal hydroxides, ammonia, amines, and quaternary ammonium compounds.
Claim 22
Dependent Claim
18 words
The method of claim 12, wherein said reaction product is solubilized with an aqueous alkali metal hydroxide solution.
Claim 23
Dependent Claim
36 words
The method of claim 12, further comprising the steps of: C. reacting an acid with the solubilized reaction product; D. filtering off the resultant salt formed; and E. reacting its filtrate with an aqueous amine solution.
Claim 24
Dependent Claim
80 words
An aqueous composition comprising: A. the solubilized product of: 1. a polyepoxide containing a 1,2-epoxy equivalency greater than 1.0; and 2. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer for 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group; and B. a curing agent.
Claim 25
Dependent Claim
80 words
An aqueous composition comprising: A. the solubilized product of: 1. a polyepoxide containing a 1,2-epoxy equivalency greater than 1.0; and 2. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer for 1 to 5, R is an organic radical having from 1 to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group; and B. a curing agent.
Claim 26
Dependent Claim
27 words
The aqueous composition of claim 21, wherein the equivalent ratio of epoxy groups in the polyepoxide to mercaptan groups in said compounds is between 1:0.25 and 1:1.25.
Claim 27
Dependent Claim
49 words
The aqueous composition of claim 21, wherein W is selected from the group consisting of --COOR', --CON(R") 2 , and --CN, where R' is an alkyl group of from 1 to 10 carbon atoms and R" is selected from the group consisting of hydrogen, lower alkyl and mixtures thereof.
Claim 28
Dependent Claim
22 words
The aqueous composition of claim 21, wherein said compound is an alkyl ester of mercaptoacetic acid or α-mercaptopropionic acid or β-mercaptopropionic acid.
Claim 29
Dependent Claim
27 words
The aqueous composition of claim 21, wherein said curing agent is selected from the group consisting of aminoplast resins, phenolic resins and a blocked or semi-blocked polyisocyanate.
Claim 30
Dependent Claim
106 words
An aqueous composition comprising: A. the solubilized reaction product of: 2. a polyepoxide having a 1,2-epoxy equivalency greater than 1.0; and 2. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1 to 5, R is an organic radical having from 1 `to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group; and B. a resin selected from the group consisting of phenolic resins, hydrocarbon resins, acrylic polymers, high molecular weight acrylic latex polymers, polyisocyanates, blocked or semi-blocked polyisocyanates and mixtures thereof.
Claim 31
Dependent Claim
106 words
An aqueous composition comprising: A. the solubilized reaction product of: 2. a polyepoxide having a 1,2-epoxy equivalency greater than 1.0; and 2. a compound containing a mercaptan group and at least one group hydrolyzable to a carboxyl group, said compound having the structural formula: HS--R--(W).sub.m wherein m is an integer from 1 to 5, R is an organic radical having from 1 `to 10 carbon atoms and W is a group hydrolyzable to a carboxyl group; and B. a resin selected from the group consisting of phenolic resins, hydrocarbon resins, acrylic polymers, high molecular weight acrylic latex polymers, polyisocyanates, blocked or semi-blocked polyisocyanates and mixtures thereof.
Claim 32
Dependent Claim
42 words
The aqueous composition of claim 26 wherein said composition based on the total weight of (A) and (B) contains from about 20 to about 80 percent by weight of (A) and from about 80 to about 20 percent by weight of (B).
Claim 33
Dependent Claim
12 words
The aqueous composition of claim 26 wherein said composition further contains pigment.
Claim 34
Dependent Claim
17 words
The aqueous composition of claim 26 wherein said resin is a high molecular weight acrylic latex polymer.
Claim 35
Dependent Claim
21 words
The aqueous composition of claim 29 wherein said acrylic polymer has a weight average molecular weight of at least about 100,000.
Claim 36
Dependent Claim
94 words
A coating composition comprising a liquid medium and a reaction product represented by the structure: ##STR3## or a mixture of (1) and (2), wherein A represents the organic radical portion of a polyepoxide resin having a 1,2-epoxy equivalent of greater than 1.0, R is an organic radical having from 1 to 10 carbon atoms, m is an integer from 1 to 5 and X is hydrogen or a moiety formed by reacting the carboxylic group with a basic compound selected from the group consisting of alkali metal hydroxides, ammonia, amines or quaternary ammonium compounds.
Claim 37
Dependent Claim
94 words
A coating composition comprising a liquid medium and a reaction product represented by the structure: ##STR3## or a mixture of (1) and (2), wherein A represents the organic radical portion of a polyepoxide resin having a 1,2-epoxy equivalent of greater than 1.0, R is an organic radical having from 1 to 10 carbon atoms, m is an integer from 1 to 5 and X is hydrogen or a moiety formed by reacting the carboxylic group with a basic compound selected from the group consisting of alkali metal hydroxides, ammonia, amines or quaternary ammonium compounds.
Claim 38
Dependent Claim
19 words
The coating composition of claim 31 wherein the liquid medium thereof is water, organic solvent or a mixture thereof.
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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) | 1980-06-13 | 1980-12-13 | 1981-06-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-13 | 1984-12-13 | 1985-06-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-13 | 1988-12-13 | 1989-06-14 | $7700.00 | Window Closed / Lapsed |