GB817039A - New benzthiazolylsulphenimides and their use as vulcanisation accelerators - Google Patents
New benzthiazolylsulphenimides and their use as vulcanisation acceleratorsInfo
- Publication number
- GB817039A GB817039A GB1461957A GB1461957A GB817039A GB 817039 A GB817039 A GB 817039A GB 1461957 A GB1461957 A GB 1461957A GB 1461957 A GB1461957 A GB 1461957A GB 817039 A GB817039 A GB 817039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary
- benzthiazolyl
- group
- prepared
- compound
- 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
- 238000004073 vulcanization Methods 0.000 title abstract 3
- -1 1,1,3,3-tetramethylbutyl compound Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 3
- 229920001971 elastomer Polymers 0.000 abstract 3
- 239000005060 rubber Substances 0.000 abstract 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229920003051 synthetic elastomer Polymers 0.000 abstract 2
- 239000005061 synthetic rubber Substances 0.000 abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- GAHCNYHAKKGGHF-UHFFFAOYSA-N 5,5-dimethylhexan-1-amine Chemical compound CC(C)(C)CCCCN GAHCNYHAKKGGHF-UHFFFAOYSA-N 0.000 abstract 1
- FEIQOMCWGDNMHM-UHFFFAOYSA-M 5-phenylpenta-2,4-dienoate Chemical compound [O-]C(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-M 0.000 abstract 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N Chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 abstract 1
- 229940117389 Dichlorobenzene Drugs 0.000 abstract 1
- 240000008528 Hevea brasiliensis Species 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 230000000111 anti-oxidant Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
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
Abstract
Natural or synthetic rubbers are vulcanized after the incorporation of a N-tertiary-octyl-bis-(benzthiazolyl-2-sulphen)-imide, e.g. the 1,1,3,3-tetramethylbutyl compound, a delayed-action accelerator of vulcanization, useful particularly in preventing scorching of the vulcanizate. The sulphenimide may be incorporated in amounts of up to 10 per cent of the rubber, preferably 0.2-3.0 per cent. The vulcanization may be effected by known methods, e.g. by heating with sulphur at 140 DEG C. for 20-30 minutes. Specified synthetic rubbers are polymers of butadiene-1,3, iso-butene and 2-chlorobutadiene-1,3 and copolymers of these with acrylonitrile, styrene, and methyl methacrylate. The rubbers may also contain fillers, channel and furnace blacks, antioxidants and pigments. An example is of a natural rubber (smoked sheet) mix containing N-1,1,3,3-tetramethylbutyl-bis-(benzthiazolyl-2-sulphen)-imide, and the properties of the vulcanizate. According to the Provisional Specification, any N-tertiary-alkyl-bis-(benzthiazolyl-2-sulphen)-imide may be used, tertiary alkyl groups specified being the tertiary butyl, amyl and hexyl radicals, and tertiary cycloalkyl groups such as 1-methyl-cyclohexyl. The N-tertiary butyl compound is used in an additional example. This material does not appear in the accepted Complete Specification.ALSO:The invention comprises benzthiazolylsulphenimides of the formula <FORM:0817039/IV (b)/1> where R is a tertiary octyl radical, e.g. the 1,1,3,3-tetramethylbutyl group. The compounds may be prepared by reacting a benzthiazolyl-2-sulphenhalide, e.g. the chloride, with a tertiary octylamine in an inert substantially anhydrous organic solvent, e.g. carbon tetrachloride, chloroform, benzene, chlorobenzene, dichlorobenzene and dibutyl ether, preferably one boiling below about 100 DEG C. Suitable temperatures are from 0-75 DEG C., preferably 20-40 DEG C. An acid acceptor is preferably present e.g. pyridine, an alkyl pyridine, or triethylamine. The compounds of the invention may also be prepared by reading benzthiazolyl-2-sulphenchloride (which may be obtained by chlorination of the benzthiazolyl disulphide) with an N-tertiary-octyl-benzthiazolyl-2-sulphenamide in an inert substantially anhydrous solvent, preferably in the presence of an acid acceptor. In examples, the compound is prepared in which R is the 1,1,3,3-tetramethylbutyl group. The compounds are useful in vulcanizing rubber (see Group IV (a)). According to the Provisional Specification, the group R may be any tertiary alkyl group, including cycloalkyl radicals, such as the tertiary butyl, amyl and hexyl groups, and 1-methyl-cyclohexyl radicals. In an example the compound in which R is tertiary butyl is prepared. This material does not appear in the accepted Complete Specification.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US731127A US2962481A (en) | 1957-05-08 | 1958-04-28 | Vulcanization of natural and synthetic rubber |
| DEI14803A DE1090665B (en) | 1957-05-08 | 1958-05-07 | Process for the preparation of N-alkyl-bis (benzthiazolyl-2-sulfen) -imides |
| FR1206095D FR1206095A (en) | 1957-05-08 | 1958-05-07 | New organic nitrogen compounds of the benzothiazylsulfenimide type |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB817039A true GB817039A (en) | 1959-07-22 |
Family
ID=1730882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1461957A Expired GB817039A (en) | 1957-05-08 | 1957-05-08 | New benzthiazolylsulphenimides and their use as vulcanisation accelerators |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB817039A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7291741B2 (en) | 2001-08-10 | 2007-11-06 | Duslo A.S. | Process of production of n-alkyl-2-benzthiazolysulfeneimides, device for their production and method of their purification |
-
1957
- 1957-05-08 GB GB1461957A patent/GB817039A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7291741B2 (en) | 2001-08-10 | 2007-11-06 | Duslo A.S. | Process of production of n-alkyl-2-benzthiazolysulfeneimides, device for their production and method of their purification |
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