Patent GB-1011839-A (GB)
Title: Phosphorus stabilizers
IPC: C07F9/6571
Filed: 1963-05-09
Abstract: A polymer of a C2 to C4 olefin is stabilized with a phosphorothiolothionic acid or a salt, ester or a disulphide derivative thereof.  Other stabilizers which may be present are esters of thiodipropionic acid, alkaline earth metal salts of fatty acids, and phenolic antioxidants. Example 22 describes the preparation of dioctylsilicon bis-(o,o-1,3-neopentylene phosphorothiolothionate <FORM:1011839/C3/1> by heating sodium neopentylene phosphorothiolothionate and dioctyl silicon dichloride in acetonitrile.ALSO:Various dithiophosphoric esters are obtained by reacting 2 moles of alcohol or 1 mole of glycol with 0.5 mole of P2S5 in benzene and then isolating the products by removing the benzene under reduced pressure.  Metal derivatives or organometallic derivates of the dithiophosphoric esters may be obtained by reaction of the ester/benzene solution with metal oxide or organo-metallic oxide.  The products obtained are:-(1) o,o-di-n-hexyl phosphorothiolothionic acid, (2) o,o-1,3-butylene phosphorothiolothionic acid, <FORM:1011839/C2/1> (3) o,o - 2 - ethyl - 1,3 - hexylene phosphorothiolothionic acid, <FORM:1011839/C2/2> (4) o,o - di - p - cresyl phosphorothiolothionic acid, (5) o,o - di - (2,2,4 - trimethylpentyl) phosphorothiolothionic acid, (6) o,o-1,3-neopentylene phosphorothiolothionic acid, <FORM:1011839/C2/3> (7) barium bis - (o.o - di - n - butyl phosphorothiolothionate), <FORM:1011839/C2/4> (8) zinc bis-(o,o-diisooctyl phosphorothiolo thionate), (9) dibutyltin bis - (o,o - dibutyl phosphorothiolothionate), <FORM:1011839/C2/5> (10) dibutyltin bis - (o,o - di - n - hexyl phosphorothiolothionate), (11) dibutyltin bis - (o,o-di - (2,2,4 - triMepentyl) phosphorothiolothionate), (12) dibutyltin - bis - (o o - 2 - ethyl-1,3 - hexylene phosphorothiolothionate), (13) dibutyltin bis - (o,o - 1,3 - neo - pentylene phosphorothiolothionate), <FORM:1011839/C2/6> (14) dibutyltin bis - (o,o - di - p - cresyl phosphorothiolothionate), (15) dioctyltin bis - (o,o-di - n - hexyl phosphorothiolothionate), (16) dioctyl tin bis - (o,o - 1,3 - butylene phosphorothiolothionate), (17) dioctyltin bis - (o,o - 2-ethyl - 1,3 - hexylene phosphorothiolothionate), (18) dioctyl tin bis - (o,o - di - (2,2,4 - triMepentyl) phosphorothiolothionate), (19) dioctyl tin bis - (o,o - 1,3 - neopentylene phosphorothiolothionate), (20) tributyl tin (o,o - diethyl phosphorothiolothionate, (21) (diethoxyphosphinothioyl) thio-(tributyltin) acetate. <FORM:1011839/C2/7> In Examples (23) o,o-1,3-neopentylene-S-(1,2 - dicarboethoxyethyl) - phosphorothiolothionate <FORM:1011839/C2/8> is obtained from o,o-1,3-neopentylene phosphorothiolothioni acid and diethyl maleate. (24) o,o - 2 - ethyl - 1,3 - hexylene S - lauryl phosphorothiolothionate is prepared from o,o-2 - ethyl - 1,3 - hexylene phosphorothiolothionic acid by treatment with sodium methoxide followed by dodecyl iodide; (25), (26) and (27) bis - [di - (2,2,4 - triMepentoxy) phosphinothioyl)] disulphide, <FORM:1011839/C2/9> bis - (di - n - hexoxy phosphinothioyl) disulphide, and bis-(1,3-oxybutylene phosphinothioyl) disulphide are prepared by hydrogen peroxide oxidation of the corresponding thiolothionic acids.