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US4128510A Expired / Lapsed US ⏱️ 0.0 years remaining

Vulcanizing halogen-containing polymers

Assignee: Hercules LLC
•
Filing: 1977-04-18
•
Granted: 1978-12-05
•
Expires: 1997-04-18
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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 16:25
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.

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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) 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

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