Patent GB-750106-A (GB)
Title: Hydrocarbontin derivatives of monomercapto-borate esters
Inventor: RAMSDEN HUGH EDWIN
IPC: C10M159/18
Filed: 1953-11-26
Abstract: Vinyl chloride and vinylidene chloride polymers and copolymers containing a plasticiser (di-2-ethylhexyl phthalate) are stabilised against heat deterioration by incorporation of a hydrocarbon tin derivative of a monomercapto borate ester, of formula <FORM:0750106/IV(a)/1> where R is a hydrocarbon radical, R1 is the residue of an alcohol, glycol, polyglycol or phenol, R11 is an unsubstituted alkylene or arylene radical, n has a value of 1 to 3 and x is 1 or 2 (see Group IV (b)).  Stabilisers specified include dibutyl tin di-s.s-(bis-dihydroabietyl mercaptoethyl borate), dibutyl tin bis-s.s-(di-2-ethylhexyl-b -mercaptoethyl borate), dibutyl tin bis-s.s-(di-2-butyl octyl mercaptoethyl borate), diphenyl tin bis-s.s-(di-phenyl mercaptoethyl borate) and a compound of formula <FORM:0750106/IV(a)/2>ALSO:The invention comprises hydrocarbon-tin derivatives of monomercapto borate esters of formula <FORM:0750106/IV(a)/1> where R is a hydrocarbon radical, R1 is the residue of an alcohol, glycol, polyglycol or phenol, R11 is an unsubstituted alkylene or arylene radical, n has a value of 1 to 3 and x is 1 or 2.  R11 may be derived from mercapto ethanol, mercapto phenol or substituted mercapto ethanols or mercapto phenols.  The compounds may be prepared by reacting a hydrocarbon tin compound such as an oxide, hydroxide or stannoic acid with a mercapto borate ester, preferably at a temperature slightly above 100 DEG  C. in order to remove water of reaction.  If the reaction is carried out below 100 DEG  C., the reaction mixture may be subsequently heated to above 100 DEG  C.  Inert organic solvents such as toluene or benzene may be used to facilitate the reaction.  The compounds of the invention may be used as stabilizers for chlorine-containing plastics especially polyvinyl chloride and polyvinylidene chloride, as rubber accelerators and antioxidants, polymerization accelerators and petroleum additives.  In an example dihydroabietyl alcohol, mercapto ethanol and boric acid are reacted in toluene to give bis-(dihydroabietyl) mercaptoethyl borate, which is further reacted with dibutyl tin oxide to give dibutyl tin di-S.S-(bisdihydroabietyl mercaptoethyl borate). Other examples describe the preparation of dibutyl tin bis-S.S-(di-2-ethylhexyl-b -mercaptoethyl borate), dibutyl tin bis-S.S-(di-2-butyloctyl mercaptoethyl borate), and diphenyl tin bis-S.S-(diphenyl mercaptoethyl borate), and a compound of formula <FORM:0750106/IV(a)/2> The preparation of the following intermediates is also described: di-(2-ethylhexyl)-b -mercaptoethyl borate, di-(2-butyloctyl)-mercaptoethyl borate, diphenyl-mercaptoethyl borate and the reaction product from ethylene glycol, mercaptoethanol and boric acid.ALSO:Hydrocarbon tin derivatives of monomercapto borate esters of formula:- <FORM:0750106/V/1> where R is a hydrocarbon radical, R1 is the residue of an alcohol, glycol or polyglycol or phenol, R11 is an unsubstituted alkylene or arylene radical, n has a value of 1 to 3 and x is 1 or 2 (see Group IV(b)) are used as rubber antioxidants and accelerators.  Specified compounds include dibutyl tin di-S.S-(bis-dihydroabietyl mercaptoethyl borate), dibutyl tin bis-S.S.-(di-2-ethylhexyl b -mercaptoethyl borate), dibutyl tin bis-S.S.-(di-2 butyloctyl mercaptoethyl borate), diphenyl tin bis-S.S.-(diphenyl mercaptoethyl borate) and a compound of formula:- <FORM:0750106/V/2>