Patent GB-498524-A (GB)
Title: A method of improving the age resisting characteristics of rubber and similar deteriorable organic materials
IPC: C08K11/00
Filed: 1937-07-12
Abstract: The age-resisting characteristics of rubber and similar deteriorable organic materials, are improved by incorporating therewith the reaction products of anhydro amino benzyl alcohols and secondary aryl amines.  The preferred anhydro amino benzyl alcohol is anhydro para amino benzyl alcohol of the formula <FORM:0498524/III/1> and the preferred amines are secondary diaryl amines.  The products are usually soft resins of unknown chemical constitution, and are used directly without any attempt to separate them into their component constituents.  The anhydro compounds are prepared by reacting formaldehyde with the appropriate amine hydrochloride in hydrochloric acid solution.  In the present application the term anhydro compound is used to denote the product obtained by reacting formaldehyde with an aromatic amine hydrochloride in acid solution.  Anhydro compounds mentioned include anhydro para amino benzyl alcohol, 2-methyl-, 3-methyl-, 2-ethyl-, 3-ethyl-, 2-methoxy-, 3-methoxy-, 2-isopropyl-, 3-isopropyl-, 2-ethoxy-and 3-ethoxy anhydro amino benzyl alcohols. The secondary amines mentioned include: diphenylamine, phenyl tolyl amine, ditolylamine, 4-methoxy and 4-ethoxy diphenylamine, phenyl alpha- and beta naphthylamine, diphenyl para phenylene diamine or other similar compounds in which preferably at least one of the para positions to the secondary amino group is unsubstituted.  In examples: (1) an alcoholic solution of phenyl beta naphthylamine is acidified with hydrochloric acid and reacted with anhydro para amino benzyl alcohol for 8 hours on a steam bath.  The product is made alkaline with sodium carbonate to yield a soft resin.  (2) The reaction between diphenyl para phenylene diamine and anhydro para amino benzyl alcohol is carried out as described in example (1).  The anti-agers prepared in examples (1) and (2) above were incorporated in a standard rubber mix, and the resulting stock tested for age resistance and flexing.  The term "rubber" includes in addition to natural rubber, rubber like materials such as balata guttapercha, reclaimed rubber, and synthetic rubber.ALSO:The age-resisting characteristics of rubber and similar deteriorable organic materials, are improved by incorporating therewith the reaction products of anhydro amino benzyl alcohols and secondary aryl amines.  The preferred anhydro amino benzyl alcohol is anhydro para amino benzyl alcohol of the formula <FORM:0498524/IV/1> and the preferred amines are secondary diaryl amines.  The products are usually soft resins of unknown chemical constitution, and are used directly without any attempt to separate them into their component constituents.  The anhydro compounds are prepared by reacting formaldehyde with the appropriate amine hydrochloride in hydrochloric acid solution.  In the present application, the term anhydro compound is used to denote the product obtained by reacting formaldehyde with an aromatic amine hydrochloride in acid solution.  Anhydro compounds mentioned include anhydro para amino benzyl alcohol, 2-methyl-, 3-methyl-, 2-ethyl-, 3-ethyl-, 2-methoxy-, 3-methoxy-, 2-isopropyl-, 3-isopropyl-, 2-ethoxy-, and 3-ethoxy anhydro amino benzyl alcohols.  The secondary amines mentioned include: diphenylamine, phenyl tolyl amine, ditolylamine, 4-methoxy and 4-ethoxy diphenylamine, phenyl alpha- and beta-naphthylamine, diphenyl para phenylene diamine or other similar compounds in which preferably at least one of the para positions to the secondary amino group is unsubstituted.  In examples: (1) an alcoholic solution of phenyl beta naphthylamine is acidified with hydrochloric acid and reacted with anhydro para amino benzyl alcohol for 8 hours on a steam bath.  The product is made alkaline with sodium carbonate to yield a soft resin; (2) the reaction between diphenyl para phenylene diamine and anhydro para amino benzyl alcohol is carried out as described in example (1). The anti-agers prepared in examples (1) and (2) above were incorporated in a standard rubber mix, and the resulting stock tested for age resistance and flexing. The term "rubber" includes in addition to natural rubber, rubber-like materials such as balata, guttapercha, reclaimed rubber, and synthetic rubber.ALSO:The age resisting characteristics of rubber and similar deteriorable organic materials, are improved by incorporating therewith the reaction products of anhydro amino benzyl alcohols and secondary aryl amines.  The preferred anhydro amino benzyl alcohol is anhydro para amino benzyl alcohol of the formula <FORM:0498524/V/1> , and the preferred amines are secondary diaryl amines.  The term "rubber" includes in addition to natural rubber, rubber like materials such as balata, guttapercha, reclaimed rubber, and synthetic rubber.