Patent GB-1001351-A (GB)
Title: Halogenated bisphenols and applications thereof
Inventor: ORLOFF HAROLD DAVID
IPC: C10M131/10
Filed: 1963-04-05
Abstract: As stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone, use is made of the formula <FORM:1001351/C4-C5/1> in which X is chlorine, bromine or iodine (see Division C2). Materials which may be so stabilized include the following:-  Animal, vegetable and fish oils and fats.-A number of products which may be stabilized are specified.  A synergistic effect is produced by using the stabilizers in association with citric acid, phosphoric acid, ascorbic acid, ethyl acid phosphate, gluconolactone, phytic acid, tartaric acid or aconitic acid. Specific compositions are described in Examples 33-37.  Silicone lubricants.-These may be polyalkyl, polyaryl, polyalkoxy or polyaryloxy siloxanes or silanes, a number being specified. Examples 15-19 describe specific compositions.  Lubricant greases.-Examples 11, 13 and 14 describe specific compositions.  Other materials which may be stabilized are: (1) petroleum products, including gasolenes, mineral lubricating oils, di-ester oils, tricresyl phosphate, hydraulic fluids and hydrocarbon waxes, (2) polyalkylene glycol lubricants prepared from an aliphatic alcohol and an alkylene oxide; (3) chlorinated lubricants, specified compounds being chlorodiphenyls, chloronaphthalenes, chloro-diphenyl oxides and chlorinated paraffin waxes, (4) polymeric fluorocarbon lubricants containing recurring groups -CF2-CF-Cl-, (5) anti-knock compositions containing a lead tetra-alkyl compound and a scavenger, a number of which are specified, and (6) soaps used in the preparation of lubricating greases. The lubricant compositions may contain known additives, a number of which are specified.ALSO:As stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone, use is made of bisphenols of the formula <FORM:1001351/C3/1> in which X is chlorine, bromine or iodine (see Division C2). Materials which may be so stabilized include (1) elastomers, which may be natural or synthetic rubber, a number of types of synthetic rubbers being specified; Examples 38-46 describe natural or synthetic rubber compositions; (2) silicones, which may be polyalkyl, polyaryl, polyalkoxy or polyaryloxy siloxanes or silanes, a number being specified; Examples 15-19 describe specific compositions; (3) polyester resins, (4) polymers of monoolefines, such as polyethylene and polypropylene; (5) epoxide resins, and (6) polystyrene, polyvinyl chloride and polyvinyl acetate.ALSO:The invention comprises bisphenols of the formula <FORM:1001351/C2/1> in which X is chlorine, bromine or iodine.  The compounds are obtainable by reacting a 4-halogen-6-tert-butylphenol with formaldehyde in the presence of an alkali-metal hydroxide and a non-aqueous solvent.  Details are given in examples 49-51.  The products are useful as stabilizing agents for organic materials which tend to deteriorate in the presence of air, oxygen or ozone. Materials which may be so stabilized include the following.  Esters having lubricating properties.-A number of acids and alcohols from which such esters can be prepared are specified, and reference is made to the stabilization of diisooctyl azelate, di-(2-ethylhexyl) sebacate, di-sec.-amyl sebacate, diisooctyl adipate, di-(2-ethylhexyl) adipate, di-(2-ethylhexyl) azelate, di - (1 - methyl - 4 - ethyloctyl) glutarate, di-isoamyl adipate, di-(2-ethylhexyl) glutarate, di-(2-ethylbutyl) adipate, di-tetradecyl sebacate, di-(2-ethylhexyl) pinate, diethyl oxalate, di-sec.-butyl malonate, di-(2-hexyl) succinate, diisoheptyl pimelate, di-(3-decyl) suberate, di-sec.-amyl glutarate, diisobutyl glutarate, di - (2 - ethylbutyl) glutarate, di - (3 - methylbutyl) adipate, diethyl adipate, di-sec.-amyl azelate, diisobutyl azelate and di-sec-butyl sebacate.  Organic phosphoric acid esters of the general formula OP(OR)(OR1)(OR11), in which R, R1 and R11 are hydrogen or organic radicals, at least one being an organic radical.  Example 25 describes the stabilization of tricresyl phosphate. Other phosphoric esters which may be treated are also specified.  Organic lead compounds for use in anti-knock compositions. Specified compounds are tetramethyl lead, tetraethyl lead, tetrapropyl lead, dimethyldiethyl lead, trimethylethyl lead and triethyl lead bromide.  Other materials which may be stabilized include chlorinated lubricants, specified compounds being chlorodiphenyls, chloronaphthalenes, chlorodiphenyl oxides and chlorinated paraffin waxes.