US4288576A
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2,5-Dimercapto-1,3,4-thiadiazole as a cross-linker for saturated, halogen-containing polymers
Assignee: Hercules LLC
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Filing: 1979-06-29
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Granted: 1981-09-08
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Expires: 1999-06-29
Abstract
Abstract It has been found that saturated, halogen-containing polymers can be cross-linked to yield stable vulcanizates using 2,5-dimercapto-1,3,4-thiadiazole in the presence of certain basic materials in normal vulcanization procedures.
Inventors
- 👤 John R. Richwine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:06
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/45; C08K5/46; C08K13/00; C08K13/02
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
125 words
The process of cross-linking a halogen-containing polymer which contains at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation, which comprises heating said polymer in the presence of 2,5-dimercapto-1,3,4-thiadiazole and a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolylguanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 2
Dependent Claim
125 words
The process of cross-linking a halogen-containing polymer which contains at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation, which comprises heating said polymer in the presence of 2,5-dimercapto-1,3,4-thiadiazole and a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolylguanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 3
Dependent Claim
15 words
The process of claim 1 wherein the saturated halogen-containing polymer is a homopolymer of epichlorohydrin.
Claim 4
Dependent Claim
18 words
The process of claim 1 wherein the saturated halogen-containing polymer is a copolymer of epichlorohydrin and ethylene oxide.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the saturated halogen-containing polymer is chlorinated polyethylene.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein the saturated halogen-containing polymer is poly(vinyl chloride).
Claim 7
Dependent Claim
13 words
The process of claim 1 wherein the saturated halogen-containing polymer is chlorosulfonated polyethylene.
Claim 8
Dependent Claim
27 words
The process of claim 1 wherein the basic material is an amine having a boiling point above about 110° C. and a pK value below about 4.5.
Claim 9
Dependent Claim
23 words
The process of claim 7 wherein the amine is selected from primary, secondary and tertiary aliphatic amines containing four to twenty carbon atoms.
Claim 10
Dependent Claim
10 words
The process of claim 7 wherein the amine is dicyclohexylamine.
Claim 11
Dependent Claim
10 words
The process of claim 7 wherein the amine is 2,2'-diethyldihexylamine.
Claim 12
Dependent Claim
32 words
The process of claim 1 wherein the basic material is a salt of an amine having a pK value below about 4.5 with an acid having a pK value above about 2.0.
Claim 13
Dependent Claim
10 words
The process of claim 1 wherein the salt is mono(2,2'-diethyldihexylammonium)-1,3,4-thiadiazole-5-thio-2-thioate.
Claim 14
Dependent Claim
27 words
The process of claim 1 wherein the basic material is a quaternary ammonium hydroxide or its salt with an acid having a pK value above about 2.0.
Claim 15
Dependent Claim
13 words
The process of claim 13 wherein the quaternary ammonium hydroxide is tetrabutylammonium hydroxide.
Claim 16
Dependent Claim
24 words
The process of claim 13 wherein the quaternary ammonium hydroxide salt with an acid having a pK value above about 2.0 is tetraethylammonium benzoate.
Claim 17
Dependent Claim
11 words
The process of claim 1 wherein the basic material is diphenyl-guanidine.
Claim 18
Dependent Claim
11 words
The process of claim 1 wherein the basic material is ditolyl-guanidine.
Claim 19
Dependent Claim
38 words
The process of claim 1 wherein the basic material is the condensation product of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 20
Dependent Claim
16 words
The process of claim 18 wherein the condensation product is the condensate of aniline with butyraldehyde.
Claim 21
Dependent Claim
15 words
The process of claim 18 wherein the inorganic base is an alkaline earth metal oxide.
Claim 22
Dependent Claim
14 words
The process of claim 20 wherein the alkaline earth metal oxide is magnesium oxide.
Claim 23
Dependent Claim
14 words
The process of claim 20 wherein the alkaline earth metal oxide is calcium oxide.
Claim 24
Dependent Claim
15 words
The process of claim 18 wherein the inorganic base is an alkaline earth metal salt.
Claim 25
Dependent Claim
15 words
The process of claim 18 wherein the inorganic base is an alkaline earth metal hydroxide.
Claim 26
Dependent Claim
119 words
A saturated halogen-containing polymer containing at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation cross-linked by heating in the presence of 2,5-dimercapto-1,3,4-thiadiazole and a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolyl-guanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 27
Dependent Claim
119 words
A saturated halogen-containing polymer containing at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation cross-linked by heating in the presence of 2,5-dimercapto-1,3,4-thiadiazole and a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolyl-guanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 28
Dependent Claim
120 words
A cross-linkable composition comprising (a) a saturated, halogen-containing polymer containing at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation, (b) 2,5-dimercapto- 1,3,4-thiadiazole and (c) a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolyl-guanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
Claim 29
Dependent Claim
120 words
A cross-linkable composition comprising (a) a saturated, halogen-containing polymer containing at least about 2% by weight of halogen and less than 0.1 mole % ethylenic unsaturation, (b) 2,5-dimercapto- 1,3,4-thiadiazole and (c) a basic material selected from (1) amines having a boiling point above about 110° C. and a pK value below about 4.5; (2) salts of amines having pK values below about 4.5 with acids having pK values above about 2.0; (3) quaternary ammonium hydroxides and their salts with acids having pK values above about 2.0; (4) diphenyl- and ditolyl-guanidines; and (5) the condensation products of aniline and at least one mono-aldehyde containing one to seven carbon atoms in combination with at least an equal amount of an inorganic base.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1984-09-07 | 1985-03-09 | 1985-09-08 | $2000.00 | Window Closed / Lapsed |
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