Patent GB-828703-A (GB)
Title: Amides of 4, 4-bis (hydroxyphenyl)-pentanoic acids and their use in synthetic resin compositions
IPC: C07C233/00
Filed: 1956-04-24
Abstract: The invention comprises the amides derived from nuclear substituted or unsubstituted 4 : 4 - bis - (hydroxyphenyl) - pentanoic acids, said substituents being alkyl groups of 1 to 5 carbon atoms or halogens, and ammonia or a monoamine, the radicals attached to the amino nitrogen atom of said monoamine consisting of at least one hydrogen atom and at least one aliphatic or aromatic radical; and also the amides derived from the acids specified above and rosin amines.  They are prepared by reacting together the acid and a suitable amine in known manner.  Specified amines include methylamine, laurylamine, stearylamine, octadecadienylamine, naphthylamines and amines derived from vegetable or fish oils or from rosin acids.  The amides may be reacted further with polyepoxides or formaldehyde (see Group IV (a)).  In examples, 4 : 4-bis-(41-hydroxyphenyl)-pentanoic acid is reacted with ammonia and the following amines: diallyl, allyl, dehydroabietyl, octyl, decyl, dodecyl, octadecyl, n-butyl and di-n-butyl amines, aniline and mixtures of hexadecyl, octadecyl, octadecenyl and octadecadienyl amines or of hexadecyl, octadecyl and octadecenyl amines.  The 4 : 4-bis-(41 - hydroxyphenyl) - pentanoic acid used in the examples may be replaced by 4 : 4-bis-(41-hydroxy-31-methyl, ethyl, amyl or chlorophenyl)- or (41-hydroxy-21-ethylphenyl)- or (41 - hydroxy - 31 : 51 - di - isopropyl or -bromo - phenyl) - or (21 - hydroxy - 41 - butyl-phenyl) - or (41 - hydroxy - 21 : 51 - diamylphenyl) - or (21 - hydroxy - 51 - methyl - 31 - chlorophenyl) - or (41 - hydroxy - 31 - methyl - 51 - chlorophenyl) - pentanoic acid.  Specifications 768,206 and 790,373 are referred to.ALSO:The amides derived from (a) nuclear substituted or unsubstituted 4 : 4 - bis - (hydroxyphenyl)-pentanoic acids, said substituents being alkyl groups of 1-5 carbon atoms or halogens, and (b) ammonia, a monoamine which has attached to the amino nitrogen atom at least one hydrogen atom and at least one aliphatic or aromatic radical, or a rosin amine (see Group IV (b)), may be reacted with polyepoxide resins or formaldehyde.  In Examples (14)-(16) a polyepoxide prepared by reacting bis - (4 - hydroxyphenyl)-dimethylmethane with an excess of epichlorhydrin, an amide prepared by reacting 4 : 4-bis-(41-hydroxyphenyl)-pentanoic acid with octylamine, octadecylamine or di-n-butylamine, and sodium ethoxide are dissolved in methyl isobutyl ketone and the mixture is formed into films which are cured by heating.  In Example (17) the amine used is aniline and the sodium ethoxide is replaced by sodium 4,4-bis - (41 - hydroxyphenyl) - pentanoate.  In Example (18) a mixture of 4 : 4-bis-(41-hydroxyphenyl)-pentanamide, formaldehyde in the form of formalin and oxalic acid as catalyst is heated with removal of water to give the methylol substitution product of the amide, which is dissolved in a mixture of butanol and methyl ethyl ketone and the solution formed nto films which are heat cured.  It is also stated that the polymers are useful for coating, moulding and adhesives.  Specifications 768,206 and 790,373 are referred to.