Patent GB-728258-A (GB)
Title: Epoxy esters and vinyl polymers and copolymers plasticised therewith
IPC: C11C3/04
Filed: 1953-01-26
Abstract: Vinyl chloride polymers, e.g. copolymers of vinyl chloride with vinyl acetate or vinylidene chloride are plasticized by acylated epoxy ricinoleates having the general formula <FORM:0728258/IV (a)/1> wherein R and R1 are C1-5 alkyl groups and T is an alkylene group having 2-6 carbon atoms, an alkylene oxyalkylene group having 4-8 carbon atoms or a polyalkylene oxyalkylene group having 6-10 carbon atoms.  The esters may be used with other plasticizers.  Specified esters are 21-acetoxy ethyl 9,10-epoxy-12-acetoxy octadecanoate, 21-(211-acetoxyethoxy)-ethyl 9,10-epoxy-12-acetoxy octadecanoate, 21-propionyl oxyethyl, 9,10-epoxy-12-acetoxy octadecanoate, 31-butyryloxypropyl, 9,10-epoxy-12-acetoxy or propionyloxy-octadecanoate, 21-(211-acetoxyethoxy) ethyl, 9,10-epoxy-12-valeroyloxy octadecanoate, 31-(311-acetoxy propoxy)-propyl, 9,10-epoxy-12-acetoxy or valeroyloxy-octadecanoate and 21-211-(2111-acetoxyethoxy)-ethoxy ethyl, 9,10-epoxy-12-acetoxy octadecanoate.  Their preparation is described (see Group IV (b)).ALSO:The invention relates to epoxy acylricinoleates having the general formula <FORM:0728258/IV (b)/1> in which R and R1 are alkyl groups having from 1 to 5 carbon atoms and T is an alkylene group having from 2 to 6 carbon atoms, an alkylene-oxyalkylene group having from 4 to 8 carbon atoms or a polyalkylene oxyalkylene group having from 6 to 10 carbon atoms. They may be prepared by treating acylated ricinoleates of the general formula <FORM:0728258/IV (b)/2> in which R, R1 and T are as defined above, with a solution of hydrogen peroxide in a C1 - 4 fatty acid or with a C1 - 4 fatty per-acid or perbenzoic acid at ordinary or slightly raised temperatures.  The acylated ricinoleates may themselves be prepared by condensing an appropriate acylated ricinoleic acid with a suitable alkylene glycol or polyalkylene glycol and reacting the resulting hydroxy ester with a C2 - 6 fatty acid or anhydride thereof.  The epoxy acylated ricinoleates may be used as textile-treating agents, lubricant additives as plasticizers for vinyl chloride polymers and copolymers (see Group IV (a)).  In an example 21 - (211 - acetoxyethoxy) - ethyl - 12 - acetoxy - D .9-octadecenoate is prepared by esterifying with acetyl chloride or acetic anhydride 21-(211-hydroxyethoxy) - ethyl - 12 - acetoxy - D .9-octadecenoate and epoxylating the product by treating with hydrogen peroxide in formic acid solution.  Other expoxy esters referred to are 21 - acetoxyethyl 9,10 - epoxy - 12 - acetoxyoctadecanoate, 21 - propionyloxyethyl 9,10-epoxy - 12 - acetoxyoctadecanoate, 31 - butyryloxypropyl 9,10 - epoxy - 12 - propionyl oxyoctadecanoate, 21 - (211 - acetoxyethoxy) - ethyl 9,10 - epoxy - 12 - valeroyloxy octadecanoate, 31 - (311 - acetoxypropoxy) - propyl 9,10-epoxy - 12 - acetoxyoctadecanoate, 31 - butyryloxy propyl 9,10 - epoxy - 12 - acetoxy octadecanoate, 31 - (311 - acetoxy propoxy) - propyl 9,10 - epoxy - 12 - valeroyloxy octadecanoate and 21 - 211 - (2111 - acetoxyethoxy) - ethoxyethyl 9,10 - epoxy - 12 - acetoxyoctadecanoate.  Other specified oxidizing agents are hydrogen peroxide solutions in acetic, propionic or butyric acid and performic, peracetic, perpropionic and perbutyric acids.