Patent GB-856388-A (GB)
Title: Improvements in or relating to synthetic polymers
Inventor: TYLER GEOFFREY JAMES
IPC: C08G69/40
Filed: 1957-09-26
Abstract: Dicarboxylic acids consisting of two p-carboxy-methoxyphenyl groups joined by an oxygen, methylene, ethylene, or trimethylene linkage, including compounds in which the phenyl rings bear alkyl substituents (see Group IV(b)), or their salts, esters, or other functional derivatives, are used in the production of synthetic linear polymers, particularly polyamides, polyesters, and polyesteramides.  For the production of polyamides, these dicarboxylic acids may be heated with aliphatic diamines containing 4-12 carbon atoms, the carbon chains being interrupted if desired by hetero atoms.  The polymerization my take place in presence of diluents such as xylene, or dyes, pigments, plasticizers, delustrants, or resins.  Small proportions of monoamines, monobasic acids or other monofunctional compounds may be present in order to control the degree of polymerization.  The diamines may be present in the form of their N-formyl derivatives and the acids may be present in the form of their ethyl esters. Specified diamines include hexamethylene, decamethylene, and N, N1-dimethylhexamethylene diamines, and ethylene bis-(3-aminopropyl) ether, and 1, 6-diamino-6-methylheptane.  In examples, a salt of 1, 2-bis-p-carboxymethoxyphenyl-ethane with hexamethylene diamine is formed and then heated under pressure in an atmosphere of nitrogen to form a polyamide which may be converted into cold-drawable filaments; the hexamethylene diammonium salt of 1, 3-di (p-carboxymethoxyphenyl) propane is formed and is then heated with acetic acid under pressure in an atmosphere of nitrogen; a methanol solution of di-(p-carboxymethoxy-phenyl) ether is mixed with a methanol solution of hexamethylene diamine, and the salt obtained is heated in nitrogen with acetic acid under pressure to form a polyamide which may be melt-spun to form filaments which after cold drawing have high tenacity.  Specification 639,733 is referred to.ALSO:The invention comprises dicarboxylic acids consisting of two p-carboxymethoxyphenyl groups joined by an oxygen, methylene, ethylene or trimethylene linkage, including compounds in which the phenyl rings contain alkyl substituents, and polyamide-yielding functional derivatives of such acids.  Specified acids are bis-p-carboxymethoxyphenyl oxide and the o-methyl substitution derivative thereof, bis-p-carboxymethoxyphenyl methane and the corresponding ethane and propane compounds.  The acids may be used as components in the production of synthetic condensation polymers such as polyamides, polyesters, and polyesteramides (see Group IV(a)).  They may be employed in the form of the free acids, their salts with aliphatic diamines, or their ethyl esters.  Diamines specified include hexamethylene diamine, decamethylene diamine, ethylene bis-(3-aminopropyl) ether, and N.N1-dimethylhexamethylene diamine.  In an example, 4-41-dinitrodibenzyl is subjected to catalytic hydrogenation to form 1-2-di (p-amino-phenyl) ethane which is diazotised and boiled to form 1-2 di (p-hydroxyphenyl)-ethane, and this compound is boiled with a solution of sodium monochloracetate to form the sodium salt of 1-2-bis (p-carboxymethoxyphenyl)-ethane, the free acid being obtained by acidification with hydrochloric acid.  In another example, 4-41-dimethoxychalcone is hydrogenated to form 1-3-di (p-methoxyphenyl) propane, which is hydrolysed to the corresponding hydroxy compound, and this is treated with sodium chloracetate to form the sodium salt of 1-3-bis-p-carboxymethoxy-phenylpropane.  In another example, 4-41-dihydroxydiphenyl ether is treated with sodium chloracetate to form di-(p-carboxymethoxyphenyl) ether. Specification 639,733 is referred to.