US4153586A
Expired / Lapsed
US
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Process of making epoxy resins modified with mercaptocarboxylates
Assignee: PPG Industries Inc
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Filing: 1978-03-13
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Granted: 1979-05-08
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Expires: 1998-03-13
Abstract
Abstract A process of making modified epoxy resins wherein a polyepoxide resin is reacted with a mercaptan compound of the formula HS--R--(COOX) m wherein R is an organic radical having from 1 to 10 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxyl group with a basic compound to form its salt and m is an integer of from 1 to 5. The compounds are reacted in the presence of a tin catalyst to produce resins of the structure B [--S--R--(COOX).sub.m ].sub.n wherein B is the residue from the ring opening reaction of an epoxide group on the polyepoxide resin molecule and the sulfhydryl hydrogen, R, X and m are as defined previously and n is at least 1. The aforementioned resins are produced without the need of a hydrolysis step. The modified epoxy resins are useful in formulating coating compositions having excellent physical and chemical properties. The resins can be dissolved or dispersed in water to form aqueous coating compositions.
Inventors
- 👤 Thomas R. Hockswender
- 👤 Marvis E. Hartman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 17:02
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/66; C09; C09D; C09D5/00; C09D5/44; C09D5/4419; C09D5/443; C09D5/4434; C09D5/4442; C09D5/4446
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
128 words
A process of making modified epoxy resins comprising reacting a polyepoxide having a 1,2-epoxy equivalency of greater than 1.0 with a mercaptan compound having the structure HS--R--(COOX) m , wherein R is an organic radical having from 1 to 10 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxylic acid with a basic compound to form its salt and m is an integer of from 1 to 5 wherein the equivalent ratio of epoxy groups in the polyepoxide to mercaptan groups is from about 1.0:0.25 to about 1.0:1.25, said process occurring in the presence of a tin catalyst so as to produce the modified epoxy resins resulting from the ring opening reaction of an epoxide group on the polyepoxide molecule and the sulfhydryl hydrogen.
Claim 2
Dependent Claim
128 words
A process of making modified epoxy resins comprising reacting a polyepoxide having a 1,2-epoxy equivalency of greater than 1.0 with a mercaptan compound having the structure HS--R--(COOX) m , wherein R is an organic radical having from 1 to 10 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxylic acid with a basic compound to form its salt and m is an integer of from 1 to 5 wherein the equivalent ratio of epoxy groups in the polyepoxide to mercaptan groups is from about 1.0:0.25 to about 1.0:1.25, said process occurring in the presence of a tin catalyst so as to produce the modified epoxy resins resulting from the ring opening reaction of an epoxide group on the polyepoxide molecule and the sulfhydryl hydrogen.
Claim 3
Dependent Claim
27 words
The process of claim 1 wherein a level of tin catalyst of from about 0.1 percent to about 5 percent based on the polyepoxide solids is present.
Claim 4
Dependent Claim
45 words
The process of claim 2 wherein the tin catalyst is selected from the group consisting of stannous chloride, stannous fluoride, stannous sulfate, tin naphthanate, tin benzoate, stannous octoate, tin butyrate, tin-2-ethylhexanoate, dibutyl tin dioctoate, dibutyl tin dilaurate, dibutyl tin diacetate, stannous acetate and mixtures thereof.
Claim 5
Dependent Claim
16 words
The process of claim 3 wherein the tin catalyst is dibutyl tin dilaurate or stannous octoate.
Claim 6
Dependent Claim
27 words
The process of claim 3 wherein the equivalent ratio of epoxy groups contained in the polyepoxide to the mercaptan groups is from about 1.0:0.5 to about 1.0:1.0.
Claim 7
Dependent Claim
20 words
The process of claim 5 wherein the level of tin catalyst is from about 0.2 percent to about 2 percent.
Claim 8
Dependent Claim
15 words
The process of claim 5 wherein the polyepoxide is a polyglycidyl ether of a polyphenol.
Claim 9
Dependent Claim
12 words
The process of claim 7 wherein the mercaptan compound is mercaptoacetic acid.
Claim 10
Dependent Claim
51 words
The process of claim 1 wherein the mercaptan compound is prepared by neutralizing a mercapto acid having a structure HS--R--(COOH) m with a tertiary amine having the structure ##STR5## wherein R 1 , R 2 and R 3 are alkyl groups or alkanol radicals having from 1 to 10 carbon atoms.
Claim 11
Dependent Claim
14 words
The process of claim 9 wherein the tertiary amine is triethanolamine, diethylethanolamine or ethyldiethanolamine.
Claim 12
Dependent Claim
18 words
The process of claim 1 wherein the reaction is carried out in the presence of an organic solvent.
Claim 13
Dependent Claim
32 words
The process of claim 5 wherein the reaction is carried out at a temperature of from about 20° C. to about 150° C. for from about 30 minutes to about 24 hours.
Claim 14
Dependent Claim
32 words
The process of claim 12 wherein the reaction is carried out at a temperature of from about 60° C. to about 100° C. for from about 1 hour to about 4 hours.
Claim 15
Dependent Claim
133 words
A process of making modified epoxy resins comprising reacting a polyepoxide having a 1,2-epoxy equivalency of greater than 1.0 with a mercaptan compound having the structure HS--R--(COOX) m wherein R is an organic radical having from 1 to 3 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxylic group with a basic compound selected from the group consisting of alkali metal hydroxide and alkoxide, ammonia, amine, quaternary ammonium and mixtures thereof and m is an integer of from 1 to 5 in the presence of from about 0.1 percent to about 5 percent of a tin catalyst selected from the group consisting of dibutyl tin dilaurate, stannous octoate and mixtures thereof, and wherein the equivalent ratio of epoxy groups to mercaptan groups is from about 1.0:0.25 to about 1.0:1.25.
Claim 16
Dependent Claim
133 words
A process of making modified epoxy resins comprising reacting a polyepoxide having a 1,2-epoxy equivalency of greater than 1.0 with a mercaptan compound having the structure HS--R--(COOX) m wherein R is an organic radical having from 1 to 3 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxylic group with a basic compound selected from the group consisting of alkali metal hydroxide and alkoxide, ammonia, amine, quaternary ammonium and mixtures thereof and m is an integer of from 1 to 5 in the presence of from about 0.1 percent to about 5 percent of a tin catalyst selected from the group consisting of dibutyl tin dilaurate, stannous octoate and mixtures thereof, and wherein the equivalent ratio of epoxy groups to mercaptan groups is from about 1.0:0.25 to about 1.0:1.25.
Claim 17
Dependent Claim
15 words
The process of claim 14 wherein the polyepoxide is a polyglycidyl ether of a polyphenol.
Claim 18
Dependent Claim
12 words
The process of claim 15 wherein the mercaptan compound is mercaptoacetic acid.
Claim 19
Dependent Claim
33 words
The process of claim 14 wherein the reaction is carried out at a temperature of from about 60° C. to about 100° C. and for from about 1 hour to about 4 hours.
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) | 1982-05-07 | 1982-11-06 | 1983-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-07 | 1986-11-06 | 1987-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-07 | 1990-11-06 | 1991-05-08 | $7700.00 | Window Closed / Lapsed |