Patent GB-1100809-A (GB)
Title: Method of stabilizing solid polymers
IPC: C10M139/00
Filed: 1965-05-11
Abstract: Solid polymers are stabilized against weathering by incorporating 0.0001 to 25 weight per cent of polyalkyl polyhydroxyalkyl alkylene polyamine of formula <FORM:1100809/C3/1> where R is C4- 50 alkyl, R1 is C2- 6 alkylene, R11 is C2- 6 alkylene and n is 0 to 4, or a borate of such a polyalkyl polyhydroxyalkyl alkylene polyamine. Phenolic antioxidants, e.g. 2,6 - di - t.-butyl-4-methylphenol may also be incorporated. The polymer may be a polymer or copolymer of ethylene, propylene, butylene, styrene, vinyl chloride, vinylidene chloride, vinyl acetate, acrylic and methacrylic esters and nitriles, and alkyl fumarates and maleates; or a polyvinyl acetal, polyformaldehyde, polyamide, polyester, polycarbonate, cellulose derivative, a phenol-, urea- or melamine-formaldehyde resin or a natural or synthetic rubber. The stabilized polymers may be used for making shaped articles and in coating compositions, particularly for exterior use. Many suitable polymers and stabilizers are listed and examples describe compositions comprising polyethylene, polypropylene or polystyrene and N,N1-di-sec.-octyl-N,N1-di(2-hydroxyethyl)-ethylene diamine, N1,N3 - di - sec. - octyl - N1,N2,N3 - tri-(2-hydroxyethyl) diethylene triamine, N1,N3-di-sec. - pentatriacontyl - N1,N2,N3 - tri - (2 - hydroxyethyl) diethylene triamine, N1,N2-di-sec. - butyl - N1,N2 - di - (2 - hydroxyethyl)-ethylene diamine, N1,N4-di-sec.-decyl -N1,N2,-N3,N4 - tetra - (3 - hydroxypropyl tripropylene tetramine; and reaction products of N,N1-di-sec. - octyl - N,N1 - di - (2 - hydroxyethyl)-ethylene diamine with isodecyl alcohol and boric acid or with tri-n-butyl borate; of N1,N3-di - sec. - octyl - N1,N2,N3 - tri - (2 - hydroxyethyl) diethylene triamine with boric acid; of N1,N3 - di - sec. - pentatriacontyl - N1,N2,N3 - tri - (2 - hydroxyethyl) diethylene triamine with boric acid; and of N,N1-di-sec.-butyl-N,N1 -di-(2-hydroxyethyl) ethylene diamine with boric acid and butyl mercaptan.ALSO:Polyalkyl polyhydroxyalkyl alkylene polyamine of formula <FORM:1100809/C2/1> where R is C4- 50 alkyl, R1 and R11 are C2- 6 alkylene and n is 0 to 4, may be prepared by reductive alkylation and subsequent oxyalkylenation of alkylene polyamines.  Alkylation may be effected by reacting the alkylene polyamine in the presence of hydrogen and a catalyst, e.g. a platinum/alumina/halogen complex or a mixture of copper, chromium and barium oxides.  After oxyalkylenation the products may be converted to borate esters, e.g. by reacting with boric acid, trialkyl borates, alkyl, cycloalkyl and aryl boric acids and boric oxide. Esterification or transesterification may be effected in organic solvents and in the presence of catalysts, e.g. alkali metal hydrogen sulphates, tin oxide and alkyl and alkoxy derivatives of tin, titanium and aluminium. Many suitable reactants are listed and examples describe the preparation of (1) N,N1 - di - (1 - methylheptyl) - N,N1 - di - di - (2hydroxyethyl) ethylene diamine from N,N1di - di - (1 methylheptyl) ethylene diamine and ethylene oxide; (2) N1,N3-di-(1-ethyl-3-methyl)pentyl - N1,N2,N3 - tri - (2 - hydroxyethyl) diethylene triamine from N1,N3-di-(1-ethyl-3 methylpentyl) diethylene triamine and ethylene oxide; (3) N1,N3 - di - sec. - pentatriacontyl N1,N2,N3 - tri - (2 - hydroxyethyl) diethylene triamine from diethylene triamine, pentatriacontanone and ethylene oxide; (5) N,N1-disec. - butyl - N,N1 - di - (2 - hydroxyethyl) ethylene diamine from ethylene diamine, methyl ethyl ketone and ethylene oxide; (6) N,N4 - di - sec. - decyl - N1,N2,N3, N4 - tetra(3 - hydroxypropyl) tripropylene tetramine from tripropylene tetramine, methyl octyl ketone and propylene oxide; and borates by reacting (7) amine (1) with boric acid and isodecyl alcohol; (8) amine (1) with tri-n-butyl borate; (9) amine (2) with boric acid; (10) amine (3) with boric acid; and (11) amine (5) with boric acid and butyl mercaptan.