GB708627A - Sulphides of secondary amines - Google Patents

Sulphides of secondary amines

Info

Publication number
GB708627A
GB708627A GB2674950A GB2674950A GB708627A GB 708627 A GB708627 A GB 708627A GB 2674950 A GB2674950 A GB 2674950A GB 2674950 A GB2674950 A GB 2674950A GB 708627 A GB708627 A GB 708627A
Authority
GB
United Kingdom
Prior art keywords
cyanoethyl
cyclohexyl
sulphur
butyl
groups
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
Application number
GB2674950A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB708627A publication Critical patent/GB708627A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/0008Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025Crosslinking 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

Diamino disulphides having the general formula NC-R1-N(R3)-Sx-N(R4)-R2-CN i which R1 and R2 are methylene, alkylmethylene, polymethylene or alkylpolymethylene groups, R3 and R4 are aromatic, araliphatic, aliphatic or cycloaliphatic groups, and x is 1, 2, 3 or 4 are used as vulcanization agents for synthetic rubbers such as butadiene-1:3-styrene or -acrylonitrile copolymers. Exemplary of R1 and R2 are methylene, methyl-methylene, dimethylene, methyl-dimethylene, trimethylene and tetramethylene groups. Exemplary of R3 and R4 are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, amyl, isoamyl, ter. amyl, hexyl, octyl, decyl, dodecyl, pentadecyl, cyclohexyl, methyl cyclohexyl, cyclohexyl substituted-cyclohexyl, benzyl hexahydrobenzyl, b -phenethyl, phenyl, chlorophenyl, chlorobenzyl, methoxyphenyl, ethoxy phenyl and tolyl groups. Sulphur-containing accelerators of the thiazole type may also be added.ALSO:The invention comprises compounds of the general formula NC-R1-N(R3)-Sx-N(R4)-R2-CN where R1 and R2 are methylene, alkylmethylene, polymethylene or alkylpolymethylene groups, R3 and R4 are aromatic, aralphatic, aliphatic or cycloaliphatic groups and x is 1, 2, 3 or 4. They are prepared by condensing a sulphur halide with an amine of the general formula NC-R1-NHR3. R1 and R2 may be methylene, methyl methylene, ethylene, methyl ethylene, propylene or butylene groups. R3 and R4 may be methyl, ethyl, propyl, isopropyl, n-butyl, sec.-butyl, amyl, isoamyl, ter.-amyl, hexyl, octyl, decyl, dodecyl, pentadecyl, cyclohexyl, methyl cyclohexyl, cyclohexyl-cyclohexyl, benzyl, hexahydrobenzyl, b -phenethyl, phenyl, chlorophenyl, methoxy-phenyl, ethoxyphenyl or tolyl radicals, many amines containing such groups being specified. The sulphides obtained may be converted to higher polysulphides by heating with sulphur or sulphur halides. In examples: (1) four molecular proportions of N-b -cyanoethyl-N-cyclohexylamine are reacted together with one molecular proportion of sulphur monochloride to give N,N1 - di - b - (cyanoethyl) - N,N1 - dicyclohexyldiamino disulphide. Heating one mol. of this product with sulphur yields higher sulphides, e.g. the corresponding tetrasulphide; (2) N,N1 - di - (b - cyanoethyl) - N,N1 - di - (n - butyl) diamino disulphide is obtained by reacting together 4 mols. of N-b -cyanoethyl-N-n-butyl amine with 1 mol. of sulphur monochloride; N : N1 - di - (b - cyanoethyl) - N,N1 - di - (n - butyl) diamino monosulphide (NC-CH2CH2-N(C4H9) -S-N(C4H9) -CH2CH2-CN) is obtained similarly using sulphur dichloride in place of sulphur monochloride; (3) N,N1 - di - (b - cyanoethyl) - N,N1 - diethyl diamino disulphide containing some higher sulphides is obtained by reacting together N-b -cyanoethyl N-ethylamine (1.5 mols.) and sulphur monochloride (0.54 mols.). N,N1-Di-(a - cyanobutyl) - N,N1 - diphenyl diamino trisulphide and N,N1-dicyanomethyl-N,N1-dicyclohexyldiamino trisulphide are also mentioned. The products are of use as vulcanization accelerators (see Groups IV (a) and V) and as insecticides and fungicides.ALSO:Diamino sulphides having the general formula NC-R1-N(R3)-Sx-N(R4)-R2-CN in p which R1 and R2 are methylene, alkylmethylene, polymethylene, or alkylpolymethylene groups, R3 and R4 are aromatic, araliphatic, aliphatic or cycloaliphatic groups, and x is 1, 2, 3 or 4 are used as vulcanization agents for natural and synthetic rubber. Exemplary of R1 and R2 are methylene, methylmethylene, dimethylene, methyl-dimethylene, trimethylene and tetramethylene groups. Exemplary of R3 and R4 are methyl, ethyl, propyl, isopropyl, n-butyl, sec. butyl, amyl, isoamyl, ter-amyl, hexyl, octyl, decyl, dodecyl, pentadecyl, cyclohexyl, methylcyclohexyl, cyclohexyl substituted-cyclohexyl, benzyl, hexahydrobenzyl, b -phenethyl, phenyl, chlorophenyl chlorobenzyl, methoxy-phenyl, ethoxy-phenyl and tolyl groups. Sulphur-containing accelerators of the thiazole type may be employed. An example describes the vulcanization of a natural rubber stock comprising smoked sheet rubber, zinc oxide, stearic acid and N-cyclohexyl 2-benzothiazole sulphenamide with N, N1-di(b -cyanoethyl) N, N1-diethyl diamino disulphide, or with N, N1-di(b -cyanoethyl)-N, N1-di(n-butyl) diamino disulphide as vulcanization agent. Another example describes the vulcanization of stocks comprising smoked sheets rubber, furnace carbon black, zinc oxide, mineral hydrocarbon softener, stearic acid, p-amino diphenyl-acetone reaction product, N-cyclohexyl 2-benzothiazole sulphenamide, with various amounts of N, N1-di(b -cyanoethyl)-N, N1-dicyclohexylamino disulphide as vulcanization agent, and also (for comparision purposes) with sulphur. Comparison of non-scorching properties is made between the vulcanized products of stocks of the above type using N, N1-di(b -cyanoethyl))-N, N1-di(n-butyl) diamino disulphide and sulphur, respectively, as vulcanization agents, a mixture of 2, 4-dinitrophenyl-thiobenzthiazole and diphenyl guanidine phthalate being employed as vulcanization accelerator in place of the sulphenamide. Examples of the preparation of the above-mentioned vulcanization agents and of N, N1-di(b -cyanoethyl)-N, N1-dicyclohexyldiamino tetrasulphide, and N, N1-di-(b -cyanoethyl)-N, N1-di(n-butyl) diamino monosulphide (see Group IV (b)). The application of the agents to the vulcanization of synthetic rubbers is also described (see Group IV (a)).
GB2674950A 1949-11-29 1950-11-02 Sulphides of secondary amines Expired GB708627A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US740537XA 1949-11-29 1949-11-29

Publications (1)

Publication Number Publication Date
GB708627A true GB708627A (en) 1954-05-05

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 After (1)

Application Number Title Priority Date Filing Date
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

Country Status (3)

Country Link
DE (1) DE869488C (en)
FR (1) FR1029005A (en)
GB (2) GB708627A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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
FR1029005A (en) 1953-05-29
GB740537A (en) 1955-11-16
DE869488C (en) 1953-03-05

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