Patent GB-759382-A (GB)
Title: Hydrocarbontin derivatives of mercapto-aliohol esters
IPC: C07F7/22
Filed: 1953-11-19
Abstract: Hydrocarbon tin derivatives of mercapto alcohol esters in which the tin atom is joined directly to at least one sulphur atom of general formula RnSn(SR1OR11)4-n where R is an alkyl, alkenyl, alkynyl, aryl or aralkyl radical, R1 is an alkylene or arylene radical, R11 is an acyl radical and n is 1, 2 or 3 (see Group IV (b)) are used as stabilizers against light and heat deterioration of polyvinyl chloride and polyvinylidene chloride compositions containing plasticizers, e.g. di-2-ethyl hexyl phthalate.  Stabilizers specified include dibutyl tin derivatives of b -mercaptoethyl laurate, decanoate, caproate, benzoate, abietate, phthalate and sebacate; diphenyl tin bis(b -mercapto)-ethyl laurate, dilauryl tin bis(p-mercaptobenzyl caproate), dimethyl tin S,S1-bis(b -phenyl-b -mercaptoethyl butyrate) and the dibutyl tin derivative of 2-ethylhexyl-b -mercapto ethyl phthalate.  Specifications 742,975, 749,722 and 750,106 are referred to.ALSO:The invention comprises hydrocarbon derivatives of mercapto-alcohol esters in which the tin atom is joined directly to at least one sulphur atom of general formula RnSn(SR1OR11)4-n where R is an alkyl, alkenyl, alkynyl, aryl or aralkyl radical, R1 is an alkylene or arylene radical, R11 is an acyl radical and n is 1, 2 or 3.  R1\h may be derived from mercapto alcohols such as beta-mercaptoethanol; 3-mercaptopropanol-1; 2-mercaptopropanol-1; 1-mercaptopropanol-2; 2-, 3- and 4-mercapto-n-butanol-1; and o-, m- and p-mercaptobenzyl alcohol.  R11 may be derived from any monobasic or polybasic aliphatic or aromatic acid, from acid chlorides and acid anhydrides provided the hydroxyl group and not the sulphhydryl group is esterified.  Specified acid and acid derivatives are acetic acid, acetic anhydride, propionic acid, valeric acid, caprylic acid, 2-ethyl hexanoic acid, lauric acid, stearic acid, abietic acid, benzoic acid, maleic acid, phthalic acid, succinic acid, adipic acid, sebacic acid and their lower alkyl esters capable of conversion to the mercapto-alcohol esters by alcoholysis.  Hydrocarbon tin oxides, hydroxides, halides and stannoic acids may be condensed with the mercapto-alcohol esters to give the compounds of the invention: when using the halides, neutralizing agents such as sodium hydroxide, sodium carbonate, sodium bicarbonate, tertiary amines and pyridine are used to remove the hydrohalic acid produced during the condensation.  The condensation may be carried out at temperatures slightly above 100 DEG  C. to remove water of reaction, or at lower temperatures followed by heating.  Organic solvents (toluene, benzene) may be used as reaction medium.  The examples describe the preparation of dibutyl tin bis(b -mercaptoethyl laurate), dibutyl tin bis(b -mercaptoethyl decanoate), dibutyl tin bis(b -mercaptoethyl caproate), dibutyl tin S,S1 bis(b -mercaptoethyl benzoate), dibutyl tin S,S1-bis(b -mercaptoethyl abietate), diphenyl tin S1S1-bis(b -mercaptoethyl laurate), dilauryl tin S1S1-bis(p - mercaptobenzyl caproate), dimethyl tin S1S1-bis(b -phenyl-b -mercaptoethyl butyrate), and the condensation products from dibutyl tin and b -mercaptoethyl phthalate, dibutyl tin and 2-ethylhexyl-b -mercaptoethyl phthalate, and dibutyl tin and b -mercaptoethyl sebacate.  The preparation of the following mercapto-alcohol esters is described: b -mercaptoethyl laurate, b -mercaptoethyl decanoate, b -mercaptoethyl phthalate, b -mercaptoethyl caproate, 2 - ethylhexyl - b  - mercaptoethyl phthalate, b  - mercaptoethyl sebacate and b -phenyl - b  - mercaptoethyl butyrate. Specifications 742,975, 749,722 and 750,106 are referred to.ALSO:Hydrocarbon tin derivatives of mercaptoalcohol esters in which the tin atom is joined directly to at least one sulphur atom of general formula RnSn(SR1OR11)n-n where R is an alkyl, alkenyl, alkynyl, aryl or aralkyl-radical, R1 is an alkylene or arylene radical, R11 is an acyl radical and n is 1, 2 or 3 (see Group IV(b)) are used as rubber antioxidants and accelerators.  Compounds specified include dibutyl tin derivatives of b -mercapto-ethyl laurate, decanoate, caproate, benzoate, abietate, phthalate and sebacate; diphenyl tin bis (b -mercapto-ethyl laurate, dilauryl tin bis (p-mercaptobenzyl caproate), dimethyl tin S, S1-bis (b -phenyl-b -mercaptoethyl butyrate), and the dibutyl tin derivative of 2 - ethylhexyl - b  - mercapto ethyl phthalate. Specifications 742,975, 749,722 and 750,106 are referred to.