Patent GB-1062804-A (GB)
Title: Sulphur-contaning substituted succinic acid diesters and their use in the stabilization of organic material
IPC: C08K5/372
Filed: 1965-06-04
Abstract: Lubricating oils, fats and oils of animal and vegetable origin, natural and synthetic gasolines, jet fuels, diesel, mineral and fuel oils are stabilized by incorporating therein a stabilizing quantity of a compound of the formula <FORM:1062804/C4-C5/1> where R1 is C8- 18 alkyl and R2 and R3 are C12- 18 alkyl.  The compounds are preferably used in a concentration of from 0.005% to about 10% by weight of the total composition together with one or more phenolic antioxidant stabilizers, e.g. phenolic triazines, phenolic phosphonates, phenolic esters or phenolic hydrocarbons, one or more U.V. light absorbers, e.g. 2 - hydroxy - 4 - methoxybenzophenone, 2 - (21 - hydroxy - 51 - methyl - phenyl) benztriazole, and one or more phosphite compounds e.g. trioctyl-, dilauryl- and tris-(nonylphenyl)-phosphites and other conventional additives, including carbon black, may also be present. The lubricating oils may be those of the aliphatic ester type and specified animal and vegetable oils and fats are linseed, menhaden, cod liver, castor, olive, rapeseed, coconut, palm, corn, sesame, peanut and cotton seed oils, butter, fat, lard and beef tallow.ALSO:The invention comprises compounds of the formula <FORM:1062804/C2/1> wherein R1 is C8- 18 alkyl and R2 and R3 are C12- 18 alkyl.  They may be prepared (i) by reacting itaconic anhydride with a suitable alcohol in the presence of p-toluene sulphonic acid and reacting the resulting itaconic acid diester with an alkylmercaptan in the presence of sodium methylate, or (ii) by reacting mercaptomethyl-succinic acid with an appropriate alcohol or a mixture of appropriate alcohols, or (iii) by reacting an alkylmercapto-methyl-succinic acid with a suitable alcohol.  The compounds are useful as stabilizers for organic materials.  In one of the examples didodecyl itaconate is obtained by reacting itaconic anhydride with n-dodecyl alcohol in the presence of p-toluene-sulphonic acid, hydroquinone and toluene.ALSO:Polymeric materials are stabilized by incorporating therein a stabilizing quantity of a compound of the formula <FORM:1062804/C3/1> where R1 is C8- 18 alkyl and R2 and R3 are C12- 18 alkyl.  The compounds are preferably used in a concentration of from 0.005% to about 10% by wt. of the total composition together with one or more phenolic antioxidant stabilizers e.g. phenolic triazines, phenolic phosphonates, phenolic esters or phenolic hydrocarbons, one or more U.V. light absorbers e.g. 2-hydroxy-4-methoxy benzophenone, 2-(21-hydroxy-51-methyl phenyl) benztriazole, and one or more phosphite compounds e.g. tri-octyl-, dilauryl-and tris (nonyl phenyl)-phosphites and other conventional additives including carbon black may also be present.  The polymeric materials include synthetic organic polymeric substances such as vinyl resins formed by the polymerization of vinyl halides or from the copolymerization of vinyl halides with unsaturated polymerizable compounds e.g. vinyl esters, a -b -unsaturated esters, a ,b -unsaturated acids, a ,b -unsaturated ketones or aldehydes and unsaturated hydrocarbons such as butadiene and styrene; poly-a -olefins and copolymers thereof; polyurethanes; polyamides such as poly(hexamethylene adipamide); polyesters such as poly (methylene terephthalates; polycarbonates; polyacetals; polystyrene; poly (ethylene oxide); copolymers such as those formed by the copolymerization of acrylonitrile, butadiene and/or styrene and urea-formaldehyde-alkyd finishes.