Patent GB-1103144-A (GB)
Title: Esters containing an alkylhydroxyphenyl group and the stabilisation of organic material therewith
Inventor: MARTIN DEXTER
IPC: C07C69/732
Filed: 1965-04-12
Abstract: As agents for stabilizing the materials specified below against deterioration due to oxidation, heat and/or light, use is made of esters of the formula <FORM:1103144/C3/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and z denotes hydrogen or the group <FORM:1103144/C3/2> (see Division C2).  Specific esters described are n-propyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert. - butyl - hydroxyphenyl)propionate], ethy 1,1,1 - tris[methylene - 3 - (3,5 - di - tert.- butyl - 4 - hydroxyphenyl)propionate] and tetra[methylene - 3 - (3,5 - di - tert.- butyl - 4 - hydroxyphenyl propionate] - methane.  The specified materials are (1) polymers or copolymers of vinyl halides, a number of copolymeric compounds being mentioned, (2) polyolefines, e.g. polyethylene, polypropylene, polybutylene and polyisoprene, (3) polyurethanes, (4) polyamides, e.g. polyhexamethylene adipamide, (5) polyesters, e.g. polymethylene terephthalates, (6) polycarbonates, (7) polyacetals, (8) polystyrene, (9) polyethylene oxide, and (10) copolymers of butadiene and styrene and (or) acrylonitrile.  A comparative example of the treatment of polypropylene is given.ALSO:As agents for stabilizing the materials specified below against deterioration due to oxidation, heat and (or) light, use is made of esters of the formula <FORM:1103144/C4-C5/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and z denotes hydrogen or the group <FORM:1103144/C4-C5/2> (see Division C2).  Specific esters described are n - propyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate], ethyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate] and tetra[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate] - methane.  The specified materials are (1) animal and vegetable fats and oils, a number of which are specified; (2) hydrocarbons, including gasoline and fuel oil; (e) waxes; (4) fatty acids; and (5) soaps.ALSO:The invention comprises esters of the formula <FORM:1103144/C2/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and Z denotes hydrogen or the group <FORM:1103144/C2/2> The esters are obtainable by reacting an alkane polyol with an acid having a radical of the second formula above, the acid being taken as such or as its anhydride or acid halide. Reference is made also to the manufacture of the esters by transesterification. Examples are given of the preparation of n-propyl 1,1,1-tris [methylene - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate], ethyl 1,1,1-tris [methylene - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate] and tetra[methylene-3-(3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate]-methane, and these esters are specifically claimed. The esters are useful for stabilizing organic materials against deterioration due to oxidation, heat or light, and reference is made to the stabilization of lubricating oils of the aliphatic ester type, e.g. di(2-ethylhexyl) azelate or pentaerythritol tetracaproate.