US4092293A
Expired / Lapsed
US
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Polymercaptans for curing epoxy resins and method of preparation thereof
Assignee: Diamond Shamrock Corp
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Filing: 1976-06-24
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Granted: 1978-05-30
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Expires: 1996-06-24
Abstract
Abstract Disclosed is a polymercaptan material and method for preparation thereof useful in the curing of epoxy resins to impart a more hydrophobic characteristic to the resultant thermoset polymers for use in applications where there is frequent contact with water. The compound described and prepared is a propoxylated ether polythiol of the structure: <IMAGE> WHEREIN Y IS AN INTEGER OF AT LEAST 1, X IS AN INTEGER OF AT LEAST 2, R is a polyol consisting of atoms of carbon, hydrogen and oxygen and free of reactive functional groups and the total number carbon atoms in R and <IMAGE> IS GREATER THAN 15.
Inventors
- 👤 Richard L. Harris
- 👤 Paul H. Goble
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 00:23
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/66
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
89 words
A polymercaptan particularly useful for curing epoxy resins to impart particular resistance to the absorption of water by the resultant thermoset polymers comprising: a propoxylated ether polythiol of the structure ##STR9## wherein y is an integer of at least 1, x is an integer of at least 2, and R is a polyol consisting of atoms of carbon, hydrogen, and oxygen having from 2 to 6 hydroxyl groups and free of reactive functional groups and the total number of carbon atoms in R and ##STR10## is greater than 15.
Claim 2
Dependent Claim
89 words
A polymercaptan particularly useful for curing epoxy resins to impart particular resistance to the absorption of water by the resultant thermoset polymers comprising: a propoxylated ether polythiol of the structure ##STR9## wherein y is an integer of at least 1, x is an integer of at least 2, and R is a polyol consisting of atoms of carbon, hydrogen, and oxygen having from 2 to 6 hydroxyl groups and free of reactive functional groups and the total number of carbon atoms in R and ##STR10## is greater than 15.
Claim 3
Dependent Claim
10 words
A polymercaptan according to claim 1 wherein R equals pentaerythritol.
Claim 4
Dependent Claim
10 words
A polymercaptan according to claim 1 wherein R equals dipentaerythritol.
Claim 5
Dependent Claim
10 words
A polymercaptan according to claim 1 wherein R equals glycerin.
Claim 6
Dependent Claim
11 words
A polymercaptan according to claim 1 wherein R equals propylene glycol.
Claim 7
Dependent Claim
10 words
A polymercaptan according to claim 1 wherein R equals trimethylolpropane.
Claim 8
Dependent Claim
10 words
A polymercaptan according to claim 1 wherein R equals sorbitol.
Claim 9
Dependent Claim
134 words
A thermoset polymer resulting from the reaction of a propoxylated ether polythiol and an epoxy resin in the presence of an amine catalyst comprising: a propoxylated ether polythiol of the structure ##STR11## wherein y is an integer of at least 1, x is an integer of at least 2 and R is polyol consisting of atoms of carbon, hydrogen and oxygen having from 2 to 6 hydroxyl groups and free of reactive functional groups, and the total number of carbon atoms in R and ##STR12## is greater than 15; and an epoxy resin wherein the resultant thermoset polymer exhibits a water absorption rate over a period of not less than six weeks of less than 0.050 grams per square inch (0.00775 grams per square centimeter) when reacted in the presence of an amine catalyst.
Claim 10
Dependent Claim
134 words
A thermoset polymer resulting from the reaction of a propoxylated ether polythiol and an epoxy resin in the presence of an amine catalyst comprising: a propoxylated ether polythiol of the structure ##STR11## wherein y is an integer of at least 1, x is an integer of at least 2 and R is polyol consisting of atoms of carbon, hydrogen and oxygen having from 2 to 6 hydroxyl groups and free of reactive functional groups, and the total number of carbon atoms in R and ##STR12## is greater than 15; and an epoxy resin wherein the resultant thermoset polymer exhibits a water absorption rate over a period of not less than six weeks of less than 0.050 grams per square inch (0.00775 grams per square centimeter) when reacted in the presence of an amine catalyst.
Claim 11
Dependent Claim
16 words
A thermoset polymer according to claim 8 having a Shore D hardness of greater than 50.
Claim 12
Dependent Claim
164 words
A process for the manufacture of polymercaptans useful in curing epoxy resins to produce thermoset polymers which exhibit particular resistance the absorption of water comprising the steps of: introducing into a reactor an allyl ether, sufficient benzene to produce a benzene to allyl ether ratio in the range of 10/1 to .001/1, and an azo catalyst having a low decomposition temperature; introducing hydrogen sulfide to obtain a substantial excess over the stoichiometric amount so that the reactants are saturated under a pressure in the range of 80 to 388 psi (5.6 to 27.3 kg. per sq. cm.) and at a temperature in the range of 20° to 90° C; gradually raising the temperature within the range of 20° to 90° C to promote the reaction; after a period of time in the range of 0 to 15 hours, venting the excess hydrogen sulfide; cooling the reaction mixture to nearly room temperature; and stripping the solvent from the reaction mixture to obtain the polymercaptan product.
Claim 13
Dependent Claim
164 words
A process for the manufacture of polymercaptans useful in curing epoxy resins to produce thermoset polymers which exhibit particular resistance the absorption of water comprising the steps of: introducing into a reactor an allyl ether, sufficient benzene to produce a benzene to allyl ether ratio in the range of 10/1 to .001/1, and an azo catalyst having a low decomposition temperature; introducing hydrogen sulfide to obtain a substantial excess over the stoichiometric amount so that the reactants are saturated under a pressure in the range of 80 to 388 psi (5.6 to 27.3 kg. per sq. cm.) and at a temperature in the range of 20° to 90° C; gradually raising the temperature within the range of 20° to 90° C to promote the reaction; after a period of time in the range of 0 to 15 hours, venting the excess hydrogen sulfide; cooling the reaction mixture to nearly room temperature; and stripping the solvent from the reaction mixture to obtain the polymercaptan product.
References Cited (Backward Citations)
US3258495A
Cited
US3472913A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-29 | 1981-11-28 | 1982-05-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-29 | 1985-11-28 | 1986-05-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-29 | 1989-11-28 | 1990-05-30 | $7700.00 | Window Closed / Lapsed |