Patent GB-494602-A (GB)
Title: Improvements in and relating to accelerators of vulcanization
IPC: C07D293/12
Filed: 1937-06-29
Abstract: The vulcanization of rubber is accelerated by the addition to the mix of a selenazyl-2-sulphide compound other than mercaptobenzoselenazole its salts and its compounds of the formula <FORM:0494602/IV/1> <FORM:0494602/IV/2> where R stands for an acyl, aryl, or substituted aminomethyl group and X stands for a valency link, or for a -CO- or -CH2-group.  Compounds mentioned as suitable for use according to the present invention include the 2-mercapto-selenazoles other than 2-mercaptobenzo-selenazole; the diselenazyl sulphides other than di(benzoselenazole)disulphide such as di(benzoselenazole) monosulphide, the metal salts of the 2-mercapto-selenazoles, such as the zinc, lead, cadmium, mercury, calcium, sodium, potassium and barium salts, excluding those of 2-mercaptobenzoselenazole; the reaction products of alkali metal salts of the mercapto selenazoles with chlorinated organic compounds such as with chlorinated ketones, mono-, and dichloracetates, mono-, and dichlor acetamides, benzal, chloride and chlor benzothiazole.  Also the reaction product of 2-mercaptobenzoselenazole with formaldehyde; of ortho nitro phenyl sulphur halides and aryl seleno halides with sodium benzoselenazyl-2-sulphides.  Addition products of amines with zinc selenazyl 2-mercaptides.  Amines mentioned include piperidine, cyclohexylamine benzyl amine, diamylamine, di-n-butyl amine, diisopropyl amine, hexahydro phenetidine, hexahydro toluidene, ethylene diamine, tetrahydro alpha furfuryl amine, N-methyl cyclohexylamine, amyl aminebutyl amine and hexylamine.  Other compounds include the reaction products of sodium benzoselenazole-2-sulphide with the following chloro compounds, N-chlor piperidine N-chlor morpholine, dimethyl chlor amine, dibutyl chlor amine, mono- and dichlor acetophenone, diphenyl carbamine chloride, imino methylene dichlorides and dichlor di-imides.  Still other compounds are the reaction products of 2-mercapto selenazoles with formaldehyde, with methylol guanidines, with the reaction product of diphenyl guanidine and formaldehyde and with methylol amides.  A number of 2-mercapto selenazoles are mentioned which are suitable for use in the reactions described above.  The term selenazyl 2-sulphide compounds and benzoselenazole 2-sulphide compounds includes compounds embodying a selenazyl or a benzoselenazyl radical with a sulphur atom attached to the mu carbon atom of the selenazole ring.  In examples: (1) metal and amine salts are prepared by adding an aqueous solution of a metal salt or an amine salt to an alkali metal salt of a 2-mercapto selenazole; (2) the preparation of guanidine and ammonia salts is described; (3) the urea, formaldehyde and 2-mercapto selenazole reaction product is prepared; (4) 2-mercapto benzoselenazole and 2-chlor benzothiazole are reacted in the presence of aluminium chloride to give benzothiazyl-benzoselenazyl monosulphide; (5) selenazyl-2-sulphide compounds are prepared by reacting a 2-mercapto selenazole, formaldehyde and a primary or a secondary amine.  Specification 298,942, [Class 70], is referred to.ALSO:The vulcanization of rubber is accelerated by the addition to the mix of a selenazyl-2 sulphide compound other than mercaptobenzoselenazole its salts and its compounds of the formula <FORM:0494602/V/1> or <FORM:0494602/V/2> where R stands for an acyl, aryl, or substituted aminomethyl group and X stands for a valency link, or for a -CO-or-CH2- group.