Patent GB-1047707-A (GB)
Title: Aromatic hydrocarbon resins
IPC: C07C59/60
Filed: 1963-06-21
Abstract: The invention comprises difunctional resinous compounds of formula <FORM:1047707/C2/1> where X is a reactive atom or group (other than hydrogen), each R is an alkyl group containing 1 to 4 carbon atoms, each R1 is hydrogen or a hydrocarbon radical containing 1 to 6 carbon atoms, and n is greater than 1.  The aromatic rings may be derived from durene, prehuitene, isodurene and 1,3-dimethyl-2,5-di-n-butyl benzene. Compounds wherein X is R2COO- may be obtained by condensing an aromatic hydrocarbon with an aldehyde and an acid R2COOH, where R2 is a hydrocarbon radical of 1 to 20 carbon atoms.  Compounds wherein X is R2COO- may be converted to compounds wherein X is -OH by alkaline hydrolysis. Compounds wherein X is -OR3-CN, where R3 is a hydrocarbon radical of 1 to 2 carbon atoms, are obtained either by reacting an alkali metal salt of a compound wherein X is -OH with a compound B-R3-A, where A and B are different halogens, and then with a cyanide, or by reacting a compound wherein X is -OH with a nitrile containing the structure -CH=C-CN. Compounds wherein X is -OR3-CN may be hydrolysed to obtain compounds wherein X is -OR3-COOH, or they may be reacted with lithium aluminium hydride or with hydrogen in the presence of platinum oxide, and then hydrolysed, to obtain compounds wherein X is -OR3-NH2.  Compounds wherein X is halogen are obtained by reacting compounds wherein X is -OH with a gaseous hydrogen halide, and may be converted to compounds wherein X is -NH2 by reaction with ammonia.  Examples are given. Other radicals which may terminate the resins are mentioned.  The compounds may be reacted with other polyfunctional compounds to obtain high molecular weight polymers.ALSO:The invention comprises synthetic resins of formula <FORM:1047707/C3/1> where X is a reactive atom or group (other than hydrogen), each R is an alkyl group containing 1 to 4 carbon atoms, each R1 is hydrogen or a hydrocarbon radical containing 1 to 6 carbon atoms, and n is greater than 1.  The aromatic rings may be derived from durene, prehuitene, isodurene, and 1,3-dimethyl-2,5-di-n-butyl benzene. Resins wherein X is R2COO- may be obtained by condensing an aromatic hydrocarbon with an aldehyde and an acid R2COOH, where R2 is a hydrocarbon radical of 1 to 20 carbon atoms.  Resins wherein X is R2COO-may be converted to resins wherein X is -OH by alkaline hydrolysis.  Resins wherein X is -OR3-CN, where R3 is a hydrocarbon radical of 1 to 2 carbon atoms, are obtained either by reacting an alkali metal salt of a resin wherein X is -OH with a compound B-R3-A, where A and B are different halogens, and then with a cyanide, or by reacting a resin wherein X is -OH with a nitrile containing the structure -CH = C-CN.  Resins wherein X is -OR3-CN may be hydrolysed to obtain resins wherein X is -OR3-COOH, or they may be reacted with lithium aluminium hydride or with hydrogen in the presence of platinum oxide, and then hydrolysed, to obtain resins wherein X is -OR3-NH2.  Resins wherein X is halogen are obtained by reacting resins wherein X is -OH with a gaseous hydrogen halide, and may be converted to resins wherein X is -NH2 by reaction with ammonia.  The resins may be used to form higher molecular weight polymers by reaction with other polyfunctional compounds.  Examples are given. Other radicals which may terminate the resins are mentioned.