Patent GB-1042898-A (GB)
Title: Polyphenyl thioethers, their production and use
IPC: C08L81/02
Filed: 1964-01-22
Abstract: Functional fluids for lubricating purposes comprise polyphenyl thioethers, of formula <FORM:1042898/C4-C5/1> wherein a is 0 or 1, Q is hydrogen or phenyl mercapto, and A and B are the same or different, and are:  (1) phenylmercapto or phenylmercaptophenylmercapto, when a is 0, and Q is 0 and Q is phenylmercapto; (3) phenylmercapto, phenylmercaptophenylmercapto, or phenylmercaptophenylmercaptophenylmercapto, or one only of A and B is hydrogen, when a is 1 and Q is hydrogen, together with a polyphenyl ether, or a phenoxy biphenyl.  The polyphenyl ether is defined as a compound of formula <FORM:1042898/C4-C5/2> wherein R1 to R6 are hydrogen, alkyl, alkoxy, phenyl, alkylphenyl, cycloalkyl, trifluoromethyl halogen, hydroxy, or a -cumyl; and x is 1 to 6. Examples are given for compositions comprising: (1) a polyphenyl ether mixture of about 65% m-bis (m-phenoxyphenoxy)benzene, 30% m - [(n - phenoxyphenoxy)(p - phenoxyphenoxy)] benzene, and 5% m-bis(p-phenoxyphenoxy) benzene, parts being by weight, with the following parts by weight of compounds of the invention:  (a) m-bis(phenylmercapto)-benzene:-0.5%, 1.0%, 2.0%, and 3.0%; (b) p-bis(phenylmercapto) benzene:-2.0%; (c) p-bis(phenylmercaptophenyl) sulphide:-1.5%; (d) m-bis(phenylmercaptophenyl) sulphide:-1.0%; (e) m-bis(m-phenylmercaptophenylmercapto) benzene:-1.0%, (f) 1,2,4-tris(phenylmercapto) benzene:-1.0%; (g) o-bis(phenylmercapto) benzene:-1.0%; (h) bis(phenylmercapto) biphenyl:-1.0%; (2) a mixture of four ring polyphenyl ethers with m-bis(phenylmercaptobenzene), 1.5% by weight; (3) m-bis-(m-phenoxyphenoxy) phenyl ether with m-bis-(phenylmercapto) benzene, 1.5% by weight. Other additives may be present, such as pour-point depressants, crystallization inhibitors or suppressants, viscosity index improvers, dyes, rust inhibitors or other oxidation inhibitors and extreme pressure lubricating property improvers.ALSO:The invention comprises polyphenyl thioethers, of formula <FORM:1042898/C2/1> wherein a is 0 or 1, Q is hydrogen or phenylmercapto, and A and B are the same or different and are : (1) phenylmercapto or phenylmercaptophenylmercapto, when a is 0, and Q is hydrogen; (2) each phenyl mercapto, when a is 0, and Q is phenylmercapto; (3) phenylmercapto, or phenylmercaptophenylmercapto, or phenylmercaptophenylmercaptophenylmercapto, or one only of A or B is hydrogen, when a is 1 and Q is hydrogen.  The compounds may be prepared by an appropriate one of the following alternatives: (a) reaction of alkali metal thiophenate with a dihalobenzene; (b) reaction of an alkali metal salt of phenylmercapto benzene-thiol with a halophenyl phenyl sulphide; (c) reaction of an alkali metal salt of a phenylmercapto benzenethiol with a dihalobenzene; (d) reaction of an alkali metal salt of thiophenol with a trihalobenzene.  Examples are given for the preparation of: (1) m-bis(phenylmercapto) benzene; (2) bis(m-phenylmercaptophenyl)sulphide; (3) 1,2,4-tris(phenylmercapto)benzene; (4) bis(phenylmercapto)biphenyl; (5) m-bis(m-phenylmercaptophenylmercapto)benzene. The compounds are suitable for use as additives to phenoxy biphenyls or polyphenyl ethers when used as lubricants (see Division C5); also the meta-linked polyphenyl thioethers may be used per se as functional fluids in heat transfer devices, and as hydraulic fluids and lubricants; m-bis(phenyl mercapto)benzene is also useful as a herbicide and insecticide (see Division A5).ALSO:m-Bis (phenylmercapto) benzene, <FORM:1042898/A5-A6/1> wherein m is one, is useful as a pre-emergent herbicide, and also as an insecticide. Examples are given for synthesis of this compound (see Division C2).