Patent GB-448126-A (GB)
Title: Improvements in or relating to the vulcanisation of rubber
IPC: C08K5/00
Filed: 1934-11-30
Abstract: Compounds of the general formula <FORM:0448126/IV/1> where RN stands for pyridine, quinoline or isoquinoline, X is a salt forming anion and, Y is a hydrocarbon radical may be prepared by reacting the cyclic nitrogen compound directly with esters or with organic halides.  In examples: (1) Benzylpyridine chloride is prepared by the interaction of pyridine and benzyl chloride at 150 DEG  C.; (2) Ethylpyridine chloride by reacting equimolecular proportions of pyridine and ethyl chloride under pressure; (3) Ethylpyridine tartrate by the interaction of two mols. of ethylpyridine chloride with one mol. of sodium tartrate; (4) Methylpyridine formate by interacting one mol. of pyridine and one mol. of methyl formate; (5) Benzylisoquinoline chloride by heating together for 1 hour at 160 DEG C. isoquinoline and benzyl chloride; (6) Benzylpyridine thioethylate by heating one mol. of sodium ethyl mercaptide with benzylpyridine chloride in absolute alcohol; (7) Benzylpyridine ethyl trithiocarbonate by treating benzylpyridine thioethylate in alcohol solution with carbon disulphide.ALSO:The vulcanization of rubber is accelerated by the incorporation in the mix of compounds of the general formula <FORM:0448126/V/1> where R N stands for pyridine quinoline or isoquinoline which may be substituted in the nucleus by alkyl, aryl, aralkyl, halogen, nitro, amino, alkoxyl and aryloxyl, X is a salt forming anion and Y is a hydrocarbon radical which when aryl may be substituted. Examples of anions which may be represented by X are:-chlorine, bromine, iodine, sulphate, thiosulphate, nitrate, acetate, formate, tartrate, thiocyanate, hydroxyl, sulphur, mercapto, carbonate, monothiocarbonate, dithiocarbonate, trithiocarbonate, phthalate, borate, nitrite, polysulphide, and those represented by -OR1 and -SR1 where R is an organic radical having a carbon atom directly attached to the oxygen or sulphur.  The radical -OR1 may represent alkoxy or aryloxy groups such as methoxy, ethoxy, butoxy, phenoxy, naphthoxy groups, and their homologues.  The radical OR1 may also represent the alkyl, aralkyl and aryl carbonates and thio-carbonates having the structure <FORM:0448126/V/2> and <FORM:0448126/V/3> where R2 represents an alkyl, aralkyl or aryl radical such as methyl, ethyl, propyl, benzyl, phenyl, or naphthyl. The radical -SR1 may represent thioalkylates or arylates such as thiomethylate or thiophenylate.  The radical -SR1 may also represent the alkyl aralkyl and aryl mono and tri-thiocarbonates having the formula <FORM:0448126/V/4> and <FORM:0448126/V/5> where R2 represents an alkyl, aralkyl, or aryl radical. Examples of organic radicals which may be represented by Y in the general formula are methyl, ethyl, propyl, isopropyl, butyl, amyl, vinyl, allyl, crotyl, lauryl, benzyl, toluyl, xylyl, phenyl, naphthyl, dinitrophenyl, dinitro-naphthyl, and 9 : 10-dihydroanthraquinyl.  A large number of compounds falling within the ambit of the general formula is given. The preparation of compounds of this type is generally effected by reacting the cyclic nitrogen compound directly with esters or organic halides. In examples: (1) Benzylpyridine chloride is prepared by the interaction of pyridine and benzyl chloride at 150 DEG  C.; (2) Ethylpyridine chloride, by reacting equimolecular proportions of pyridine and ethyl chloride under pressure; (3) Ethylpyridine tartrate, by the interaction of two mols. of ethylpyridine chloride and one mol of sodium tartrate; (4) Methylpyridine formate, by interacting one mol. of pyridine and one mol. of methyl formate; (5) Benzylisoquinoline chloride by heating together for 1 hour at 160 DEG C. isoquinoline and benzyl chloride; (6) Benzylpyridine thioethylate, by heating one mol. of sodium ethyl mercaptide with benzylpyridine chloride in absolute alcohol; (7) Benzylpyridine ethyl trithiocarbonate, by treating benzylpyridine thioethylate in alcohol solution with carbon disulphide.  Specifications 421,533 and 422,136 are referred to.  The Specification as open to inspection under Sect. 91 comprises also the use as accelerators of vulcanization of compounds of the general formula <FORM:0448126/V/6> in which R and R1 are the terminal carbon atoms of a closed chain which may include an arylene grouping.  X and Y have the same significance as in the accepted Specification.  This subject-matter does not appear in the Specification as accepted.