GB802079A - Benzthiazyl sulphenamides and their use as vulcanization accelerators - Google Patents
Benzthiazyl sulphenamides and their use as vulcanization acceleratorsInfo
- Publication number
- GB802079A GB802079A GB2221955A GB2221955A GB802079A GB 802079 A GB802079 A GB 802079A GB 2221955 A GB2221955 A GB 2221955A GB 2221955 A GB2221955 A GB 2221955A GB 802079 A GB802079 A GB 802079A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzthiazyl
- reaction
- compounds
- sulphenamide
- vulcanization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A process for the vulcanization of natural or synthetic rubber comprises incorporating in the rubber before vulcanization an N-1-alkylcyclohexylbenzthiazole-2-sulphenamide of the formula: <FORM:0802079/IV (a)/1> wherein R stands for an alkyl radical, e.g. methyl, ethyl, n-propyl or a higher straight chain homologue, and then vulcanizing the mixture so obtained. The synthetic rubbers used include polymers of butadiene-1 : 3, iso-buteneALSO:The invention comprises N-1-alkylcyclohexylbenzthiazyl-2-sulphenamides of the formula <FORM:0802079/IV (b)/1> wherein R stands for an alkyl radical. The novel compounds may be obtained by reaction of benzthiazyl-2-sulphenamide with a 1-alkylcyclohexylamine, preferably by heating the reactants together, in the presence or absence of a solvent, at temperatures between 35 DEG and 80 DEG C. It is preferred to use an excess of the amine and to remove the excess after reaction by, for example, distillation under atmospheric or reduced pressure, or by washing with a solvent for the amine, e.g. water. The compounds may also be obtained by reaction of N-monochloro - 1 - alkyl - cyclohexylamine with sodium 2-mercaptobenzthiazole, or by reaction of 2-benzthiazylsulphenyl chloride with a 1-alkylcyclohexylamine. The alkyl radical in the compounds may be, for example, methyl, ethyl, n-propyl or a higher straight-chain homologue. The compounds are useful as delayed-action accelerators in the vulcanization of natural and synthetic rubbers. In an example, benzthiazyl - 2 - sulphenamide and 1 - methylcyclohexylamine are heated at 55-60 DEG C. with stirring for 5 hours to obtain benzthiazyl-2-sulphen-(11-methylcyclohexyl)-amide.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE549939D BE549939A (en) | 1955-08-02 | ||
| NL97935D NL97935C (en) | 1955-08-02 | ||
| GB2221955A GB802079A (en) | 1955-08-02 | 1955-08-02 | Benzthiazyl sulphenamides and their use as vulcanization accelerators |
| DEI12017A DE1049087B (en) | 1955-08-02 | 1956-08-01 | Vulcanization accelerator |
| FR1155349D FR1155349A (en) | 1955-08-02 | 1956-08-02 | New nitrogenous organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2221955A GB802079A (en) | 1955-08-02 | 1955-08-02 | Benzthiazyl sulphenamides and their use as vulcanization accelerators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB802079A true GB802079A (en) | 1958-10-01 |
Family
ID=10175853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2221955A Expired GB802079A (en) | 1955-08-02 | 1955-08-02 | Benzthiazyl sulphenamides and their use as vulcanization accelerators |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE549939A (en) |
| DE (1) | DE1049087B (en) |
| FR (1) | FR1155349A (en) |
| GB (1) | GB802079A (en) |
| NL (1) | NL97935C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB865334A (en) * | 1958-06-05 | 1961-04-12 | Firestone Tire & Rubber Co | N-(propynyl)-2-(thiazole) sulfenamides |
| FR2989227B1 (en) | 2012-04-06 | 2014-05-02 | Commissariat Energie Atomique | BATTERY OF ACCUMULATORS PROTECTED AGAINST ELECTRIC ARCS |
-
0
- NL NL97935D patent/NL97935C/xx active
- BE BE549939D patent/BE549939A/xx unknown
-
1955
- 1955-08-02 GB GB2221955A patent/GB802079A/en not_active Expired
-
1956
- 1956-08-01 DE DEI12017A patent/DE1049087B/en active Pending
- 1956-08-02 FR FR1155349D patent/FR1155349A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL97935C (en) | |
| DE1049087B (en) | 1959-01-22 |
| FR1155349A (en) | 1958-04-25 |
| BE549939A (en) |
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