Patent US4128510A successfully refreshed from Google Patents.
US4128510A
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Vulcanizing halogen-containing polymers
Assignee: Hercules LLC
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Filing: 1977-04-18
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Granted: 1978-12-05
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Expires: 1997-04-18
Abstract
Abstract Halogen-containing polymers can be crosslinked by heating with certain derivatives of 2,5-dimercapto-1,3,4-thiadiazole, such as the monobenzoate derivative, and a basic material to produce useful vulcanizates of increased strength and insolubility in organic solvents. Concentrates of the derivatives of 2,5-dimercapto-1,3,4-thiadiazole may be prepared by incorporating the thiadiazole in a binder material such as a polymer, wax, rosin, etc. for subsequent compounding with the halogen-containing polymer to be crosslinked.
Inventors
- 👤 John R. Richwine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:28
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/45; C08K5/46
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
211 words
The process of crosslinking a halogen-containing polymer which consists essentially of heating said polymer in the presence of a basic material and a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR8## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR9## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR10## --SO 2 --, --SS--, ##STR11## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 2
Dependent Claim
211 words
The process of crosslinking a halogen-containing polymer which consists essentially of heating said polymer in the presence of a basic material and a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR8## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR9## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR10## --SO 2 --, --SS--, ##STR11## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein the said derivative of 2,5-dimercapto-1,3,4-thiadiazole is the monobenzoate derivative.
Claim 4
Dependent Claim
15 words
The process of claim 1 wherein the said derivative of 2,5-dimercapto-1,3,4-thiadiazole is the dibenzoate derivative.
Claim 5
Dependent Claim
15 words
The process of claim 1 wherein the said basic material is a basic metal oxide.
Claim 6
Dependent Claim
13 words
The process of claim 4 wherein the basic metal oxide is magnesium oxide.
Claim 7
Dependent Claim
15 words
The process of claim 1 wherein the said basic material is a basic metal salt.
Claim 8
Dependent Claim
13 words
The process of claim 6 wherein the basic metal salt is barium carbonate.
Claim 9
Dependent Claim
15 words
The process of claim 1 wherein the said basic material is a basic metal hydroxide.
Claim 10
Dependent Claim
13 words
The process of claim 8 wherein the basic metal hydroxide is calcium hydroxide.
Claim 11
Dependent Claim
14 words
The process of claim 1 wherein the halogen-containing polymer is a polymer of epihalohydrin.
Claim 12
Dependent Claim
203 words
A halogen-containing polymer crosslinked by heating in the presence of a basic material and a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR12## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR13## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR14## --SO 2 --, --SS--, ##STR15## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 13
Dependent Claim
203 words
A halogen-containing polymer crosslinked by heating in the presence of a basic material and a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR12## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR13## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR14## --SO 2 --, --SS--, ##STR15## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 14
Dependent Claim
13 words
The product of claim 11 wherein said halogen-containing polymer is an epihalohydrin polymer.
Claim 15
Dependent Claim
15 words
The process of claim 1 wherein the said derivative of 2,5-dimercapto-1,3,4-thiadiazole has the formula ##STR16##
Claim 16
Dependent Claim
85 words
The process of claim 1 wherein the said derivative of 2,5-dimercapto-1,3,4-thiadiazole has the formula ##STR17## wherein m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR18## --SO 2 --, --SS--, ##STR19## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 17
Dependent Claim
11 words
The process of claim 1 wherein the halogen-containing polymer is polychloroprene.
Claim 18
Dependent Claim
14 words
The process of claim 1 wherein the halogen-containing polymer is chlorinated high density polyethylene.
Claim 19
Dependent Claim
11 words
The product of claim 11 wherein the halogen-containing polymer is polychloroprene.
Claim 20
Dependent Claim
14 words
The product of claim 11 wherein the halogen-containing polymer is chlorinated high density polyethylene.
Claim 21
Dependent Claim
205 words
A crosslinkable composition consisting essentially of (a) a halogen-containing polymer, (b) a basic material, and (c) a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR20## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR21## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR22## --SO 2 --, --SS--, ##STR23## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
Claim 22
Dependent Claim
205 words
A crosslinkable composition consisting essentially of (a) a halogen-containing polymer, (b) a basic material, and (c) a derivative of 2,5-dimercapto-1,3,4-thiadiazole selected from those derivatives having one of the following formulas: ##STR20## wherein X is a substituent selected from hydrogen, --CRR'OH, --(CH 2 --CH 2 --O) n H, ##STR21## where n is an integer from 1 to 5, R and R' are selected from hydrogen, alkyl groups containing 1-8 carbon atoms, and aryl, alkaryl and aralkyl groups containing 6 to 8 carbon atoms; R 2 is selected from alkyl groups containing 1-17 carbon atoms, aryl groups containing one to two rings, alkaryl groups containing 7-14 carbon atoms, aralkyl groups containing 7-8 carbon atoms and cyclohexyl groups; R 3 is an alkyl group containing 1-8 carbon atoms; X' is the same as X with the exception of hydrogen; m is an integer from 1 to 10; and Y is selected from zinc, lead, --CRR'--, --CO--, --S--, ##STR22## --SO 2 --, --SS--, ##STR23## where R 4 is selected from alkylene and alkenylene groups containing 1-8 carbon atoms and cycloalkylene, arylene and alkarylene groups containing 6-8 carbon atoms; z is 0 or 1; and R 5 is selected from alkylene groups containing 2-8 carbon atoms, phenylene, methylphenylene and methylenediphenylene.
References Cited (Backward Citations)
US2685588A
Cited
US2760933A
Cited
US2736729A
Cited
US2983715A
Cited
US3026305A
Cited
GB974915A
Cited
US3341491A
Cited
US3357956A
Cited
US3700650A
Cited
US3732191A
Cited
US3898203A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |