GB740537A - Improvements in or relating to new composition of matter and method of making the same - Google Patents
Improvements in or relating to new composition of matter and method of making the sameInfo
- Publication number
- GB740537A GB740537A GB260452A GB260452A GB740537A GB 740537 A GB740537 A GB 740537A GB 260452 A GB260452 A GB 260452A GB 260452 A GB260452 A GB 260452A GB 740537 A GB740537 A GB 740537A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyanoethyl
- tert
- disulphide
- mol
- diamino
- 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
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention comprises diamino sulphides having the general formula <FORM:0740537/IV(a)/1> where R1 and R2 are methylene, alkylmethylene, polymethylene or alkylpolymethylene groups containing less than 5 carbon atoms and R3 and R4 are tertiary alkyl groups containing at least 8 carbon atoms or substituted alkyl groups in which the substituents are chloro, cyano, alkoxy, amino or N-cyanoalkylaminoalkyl groups, and x is an integer. Such compounds are obtained by reacting a sulphur halide with an aminoalkyl nitrile having the formula NC-R1-NH-R3. Where R3 and R4 in the product are both N-cyanoalkylaminoalkyl groups the product can be reacted with an additional molecular proportion of a sulphur monohalide. In examples: (1) one molecular proportion of di-(b -cyanoethyl) amine is reacted in benzene with 0.25 molecular proportion of sulphur monochloride, by-product amine hydrochloride is treated with sodium hydroxide, and the reaction then completed by the addition of a further 0.25 molecular proportion of sulphur monochloride and a further 0.5 mol. of sodium hydroxide, to give N,N,N1,N1-tetra-(b -cyanoethyl)-diamino disulphide; (2) 1 mol. of N,N1-di - (b - cyanoethyl) - 1,6 - hexamethylene diamine (obtained by the reaction of 1 mol. of 1,6-hexamethylene diamine with 2 mols. of acrylonitrile in aqueous medium) is reacted with 0.5 mol. of sulphur monochloride to give N,N1 - di - (b - cyanoethyl) - N,N1 - di - (o - [b - cyanoethylamino) - n - hexyl) - diamino disulphide which is further reacted with 0.5 mols. of sulphur monochloride in the presence of sodium hydroxide to give N,N1-di-(b -cyanoethyl - N(1),N1(6) - hexamethylenediamino disulphide of the formula <FORM:0740537/IV(a)/2> where n is 1 or 2 and probably 2; (3) one mol. of b - tert. - octylaminopropionitrile is reacted with 0.25 mol. of sulphur monochloride, and after the addition of sodium hydroxide with a further 0.25 mol. to give N,N1-di-(b -cyanoethyl) - N,N1 - di - b - tert. - octyldiamino disulphide. Other compounds mentioned are the sulphides of b -tert.-decylaminopropionitrile, b -tert. - dodecylaminopropionitrile and b - tert. - pentadecylaminopropionitrile. The products are useful as vulcanization agents for rubber (see Group V).ALSO:As curing agents for rubber there are specified compounds of the formula <FORM:0740537/V/1> in which x is an integer and R1 and R2 are like or unlike methylene, alkylmethylene, polymethylene or alkylpolymethylene groups containing less than 5 carbon atoms and R3 and R4 are tertiary alkyl groups containing at least eight carbon atoms or substituted alkyl groups in which the substituents are chloro, cyano, alkoxy, amino or N-cyanoalkylaminoalkyl groups. The preparation is described (see Group IV(b)) of N.N.N1.N1-tetra- (b -cyanoethyl)-diamino disulphide, N.N1-di (b -cyanoethyl)-N(1).N(6)-hexamethylenediamino disulphide having the formula <FORM:0740537/V/2> where n is 1 or 2, and probably 2, and of N.N1-di (b -cyanoethyl)-N.N1-di-b -tert. octyldiamino disulphide. Also mentioned are the sulphides of b -tert. decylaminopropionitrile, and b -tert. dodecylaminopropionitrile p and b -tert. pentadecylaminopropionitrile. As an illustration: to a composition of smoked sheet rubber, carbon black, zinc oxide, mineral hydrocarbons softener, stearic acid para-amino-diphenyl-acetone reaction product, and N-cyclohexyl-2-benzothiazole there is added N.N.N1-N1-tetra-(b -cyanoethyl) diamino disulphide, and the mixture is cured by heating in a press at 292 DEG F.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US740537XA | 1949-11-29 | 1949-11-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB740537A true GB740537A (en) | 1955-11-16 |
Family
ID=9742495
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2674950A Expired GB708627A (en) | 1949-11-29 | 1950-11-02 | Sulphides of secondary amines |
GB260452A Expired GB740537A (en) | 1949-11-29 | 1952-01-31 | Improvements in or relating to new composition of matter and method of making the same |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2674950A Expired GB708627A (en) | 1949-11-29 | 1950-11-02 | Sulphides of secondary amines |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE869488C (en) |
FR (1) | FR1029005A (en) |
GB (2) | GB708627A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1262017B (en) * | 1957-01-05 | 1968-02-29 | Firestone Tire & Rubber Co | Process for vulcanizing rubber mixtures containing furnace soot |
-
1950
- 1950-11-02 GB GB2674950A patent/GB708627A/en not_active Expired
- 1950-11-26 DE DE1950M0007646 patent/DE869488C/en not_active Expired
- 1950-11-27 FR FR1029005D patent/FR1029005A/en not_active Expired
-
1952
- 1952-01-31 GB GB260452A patent/GB740537A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1262017B (en) * | 1957-01-05 | 1968-02-29 | Firestone Tire & Rubber Co | Process for vulcanizing rubber mixtures containing furnace soot |
Also Published As
Publication number | Publication date |
---|---|
GB708627A (en) | 1954-05-05 |
FR1029005A (en) | 1953-05-29 |
DE869488C (en) | 1953-03-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4520154A (en) | Organic thiosulphates and thiosulphonates useful as stabilizing agents for rubber vulcanizates | |
JPH01174548A (en) | Modified rubber and composition, manufacturing method thereof | |
JPS58167634A (en) | Vulcanizable rubber composition | |
GB740537A (en) | Improvements in or relating to new composition of matter and method of making the same | |
US3138571A (en) | Antioxidants and antiozonants | |
US3839303A (en) | Inhibiting premature vulcanization with aminothiopyrimidines | |
EP0129527B1 (en) | Vulcanisable rubber composition and compounds useful as stabilising agents for rubber vulcanisates | |
KR20010045644A (en) | The rubber compound for tire | |
US2757174A (en) | New compositions of matter | |
GB377253A (en) | New sulphur-containing compounds and their application as vulcanisation accelerators for rubber and rubber like substances | |
US2340650A (en) | Vulcanization of rubber | |
US1874639A (en) | Rubber vulcanization accelerator | |
GB711236A (en) | Improvements in or relating to process of vulcanizing rubber and the vulcanized rubber resulting from the said process | |
US3496153A (en) | Sulfur vulcanizate of a diene rubber using a carbazinate derivative as accelerator | |
DE2540018A1 (en) | THIOAMINOPHOSPHAZENE | |
US2382792A (en) | Plasticizing neoprene | |
US2582670A (en) | Method of vulcanizing rubber and products thereof | |
US2167385A (en) | Vulcanization accelerator | |
US1779375A (en) | Method of vulcanizing caoutchouc and the product derived therefrom | |
US1674122A (en) | Process of accelerating rubber vulcanization and product thereof | |
US3796683A (en) | Vulcanization of natural and synthetic rubbers from halogen free dienes | |
US2647935A (en) | Method of vulcanizing rubber and products thereof | |
US2013117A (en) | Vulcanization of rubber | |
US3271453A (en) | 2, 5-di-tert-butyl-nu, nu'-diaryl-p-phenylenediamines | |
US1946704A (en) | Vulcanization of rubber |