Patent GB-753998-A (GB)
Title: Hydrocarbontin derivatives of esters of aliphatic and aromatic hydroxy acids
Inventor: WEINBERG ELLIOTT L
IPC: C07F7/22
Filed: 1954-03-01
Abstract: Polyvinyl chloride compositions containing if desired, plasticizers such as dioctyl phthalate are stabilized against heat and light deterioration by incorporation of a hydrocarbon tin derivative of an alkyl, aryl or aralkyl ester of a saturated or unsaturated aliphatic or aromatic hydroxy acid, of general formula <FORM:0753998/IV(a)/1> where R is an alkyl, aryl or aralkyl group, R1 is an aliphatic or aromatic hydrocarbon radical, R11 is an aliphatic hydrocarbon, ether-linked hydrocarbon or aromatic hydrocarbon radical, n is 2 or 3, m is the number of COOH groups in the acid molecule and is 1, 2 or 3, and x represents the number of OH groups in the alcohol or glycol molecule and is 1 or 2 (see Group IV (b)).  Specified stabilizers include the dibutyl tin derivatives of diethylene glycol diricinoleate, methyl ricinoleate, methyl salicylate, dibutyl tartrate, tributyl citrate, ethyl lactate, ethyl x-hydroxy isobutyrate, triethyl citrate and the trimethyl tin derivative of tributyl citrate.ALSO:The invention comprises hydrocarbon tin derivatives of alkyl, aryl or aralkyl esters of saturated or unsaturated aliphatic or aromatic hydroxy acids.  The derivatives may be of general formula <FORM:0753998/IV(a)/1> where R is an alkyl, aryl or aralkyl group, R1 is an aliphatic or aromatic hydrocarbon radical, R11 is an aliphatic hydrocarbon, ether-linked hydrocarbon or aromatic hydrocarbon radical, n is 2 or 3, m is the number of COOH groups in the acid molecule and is 1, 2 or 3, and x represents the number of OH groups in the alcohol or glycol molecule and is 1 or 2. When R11 is the residue of a glycol, the -COO-grouping may form part of a heterocyclic ring.  R may be methyl, butyl, lauryl or phenyl and R1 may be derived from ricinoleic, salicylic, tartaric, citric or lactic acid.  The compounds may be prepared by reacting a hydrocarbon-tin mono- or dihalide with a hydroxy-acid ester in the presence of a neutralizing agent, e.g. sodium hydroxide, sodium carbonate, butylamine, ammonia or pyridine.  Reaction may be conducted at temperatures above 100 DEG  C. to remove water of reaction, or at lower temperatures with subsequent further heating to remove water of reaction.  Inert organic solvents (toluene, benzene or ether) may be used to facilitate the reaction.  In an example the dibutyl tin derivative of diethylene glycol diricinoleate is prepared by reacting dibutyl tin dichloride and diethylene glycol diricinoleate in the presence of pyridine using ether as a reaction medium.  Other examples describe the preparation of dibutyl tin derivatives of methyl ricinoleate, methyl salicylate, dibutyl tartrate, tributyl citrate, ethyl lactate, ethyl a -hydroxy isobutyrate, triethyl citrate, and the trimethyl tin dreivative of tributyl citrate.ALSO:Hydrocarbon tin derivatives of alkyl, aryl or aralkyl esters of saturated or unsaturated aliphatic or aromatic hydroxy acids are used as rubber accelerators and anti - oxidants. The compounds are of formula:-  <FORM:0753998/V/1> where R is an alkyl, aryl or aralkyl group, R1 is an aliphatic or aromatic hydrocarbon radical, R11 is an aliphatic hydrocarbon, ether-linked hydrocarbon or aromatic hydrocarbon radical, n is 2 or 3, m is the number of COOH groups in the acid molecule and is 1, 2 or 3 and x represents the number of OH groups in the alcohol or glycol molecule and is 1 or 2 (see Group IV(b)).  Specified stabilizers include the dibutyl tin derivatives of dietheylene glycol diricinoleate, methyl ricinoleate, methyl salicylate, dibutyl tartrate, tributyl citrate, ethyl lactate, ethyl a  - hydroxy isobutyrate, triethyl citrate, and the trimethyl tin derivative of tributyl citrate.