Patent GB-926999-A (GB)
Title: Improvements in or relating to synthetic polyamides
Inventor: WHITTAKER KENNETH
IPC: C07C59/66
Filed: 1960-05-28
Abstract: Linear polyamides of high molecular weight are obtained by heating an aliphatic diamine containing 4 to 12 carbon atoms with a naphthylene di-(O)-glycollic acid, the glycollic acid residues being situated one in each ring but not in the peri position, or a polyamide-yielding functional derivative of said diamine and/or acid, or a salt derived from said diamine and acid, so as to effect condensation polymerization.  The process may be carried out in the presence of adjuvants or diluents, e.g. xylenes, and preferably in the presence of an inert atmosphere.  Suitable aliphatic diamines specified are hexamethylene diamine, 3-methylhexamethylene diamine, tetramethylene diamine, decamethylene diamine, octamethylene diamine, ethylene bis-(3-aminopropyl)-ether, 1:6-diamino-6-methyl heptane and N:N1-dimethyl-hexamethylene diamine.  The diamines may be used in the form of the N-formyl derivatives and the acids in the form of their ethyl esters.  Preferably equimolar proportions of the diamine and dibasic acid are employed.  The process may be carried out in the presence of viscosity stabilizers, e.g. acetic acid, and other adjuvants, e.g. dyes, pigments, dyestuff formers, plasticizers, delustrants and resins may be incorporated into the polyamides at any convenient stage in their manufacture. Interpolyamides derived from the above homopolyamides may be made by heating together the aliphatic diamine and naphthylene-di-(O)-glycollic acid with other polyamide-forming reagents, e.g. aliphatic amino carboxylic acids having from 5 to 11 carbon atoms or their lactams, or other dicarboxy acids, or by heating the above homopolyamides with another linear homopolyamide.  In the examples homopolyamides are prepared by reacting (6) hexamethylene diamine with 1:5-naphthylene di-(O)-glycollic acid (7) decamethylene diamine with 2:6-naphthylene di-(O)-glycollic acid and (8) hexamethylene diamine with 2:7-naphthylene di-(O)-glycollic acid; interpolyamides are prepared by reacting (9) hexamethylene diammonium adipate with hexamethylene diammonium naphthylene 2:7-di-(O)-glycollate and (10) polyhexamethylene adipamide with polyhexamethylene naphthylene 2:7-di-(O)-glycollamide. Specification 639,733 is referred to.ALSO:Naphthylene di-(O)-glycollic acids, the glycollic acid residues being situated one in each ring but not in the peri position, are prepared by reacting monochloracetic acid with the corresponding dihydroxy naphthalene.  In Example (1) a mixture of 1:5 dihydroxy naphthalene, monochloracetic acid and dioxan is heated under reflex until the dioxan boils.  An aqueous solution of potassium hydroxide is added to the stirred mixture followed by water and the mixture heated to maintain boiling and stirred for 15 minutes.  The mixture is cooled, acidified with HCl and solid filtered off.  After drying the solid is added to a mixture of methanol, dioxan and sulphuric acid and the whole boiled under reflux for 8 hours.  After cooling the dimethylester g 1:5 naphthylene di-(O)-glycollic acid is filtered off and recrystallised from glacial acetic acid.  The ester is hydrolysed to the dicarboxylic acid by boiling under reflux with a solution of KOH in equal parts of methanol and water and adding HCl.  The other acids are prepared in an analogous manner.  Specification 639,733 is referred to.