Patent GB-829011-A (GB)
Title: Improvements in and relating to polyesteramides
IPC: C08G69/44
Filed: 1956-04-26
Abstract: New amide group containing dicarboxylic acids and their esters have the formula <FORM:0829011/IV (b)/1> wherein R1 is an alkylene group having 4-8 carbon atoms and R11 is hydrogen or an alkyl, aryl or aralkyl group, e.g. a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl or a phenyl group.  The compounds are made by reacting at least 2 mols. of p-amino benzoic acid or an ester thereof with 1 mol. of a halide of a straight or branched chain alkylene dicarboxylic acid of formula HOOC.R1.COOH.  In examples: (1) bis-(N-p-carbethoxyphenyl) adipamide is made by dissolving ethyl p-aminobenzoate in benzene, adding alternately in small volumes adipyl chloride and sodium hydroxide solution and finally recrystallizing the reaction product from ethanol; (2), (3) and (4) bis-(N-p-carbethoxyphenyl) - sebacamide, suberamide and azelamide are similarly prepared using sebacoyl chloride, suberoyl chloride and azeloyl chloride.  The acids or esters are polycondensed with glycols to produce polyesteramides (see Group IV (a)).  Intermediates in the production of such polyesteramides are bis-glycol esters of formula <FORM:0829011/IV (b)/2> where R is an alkylene group of 2-10 carbon atoms.  Specification 824,308 is referred to.ALSO:New polysteramides having a high melting-point, good dyeability and good process ability are made by polyesterifying a glycol of formula -OH-R-OH, where R is an alkylene group of 2-10 carbon atoms, with a dicarboxylic acid or ester thereof of formula <FORM:0829011/IV (a)/1> where R1 is an alkylene group containing 4-8 carbon atoms and R11 is a hydrogen atom or an alkyl, aryl or aralkyl group.  The glycols are preferably straight-chain glycols but other glycols, e.g. 2,2-dimethyl-propanediol-1,3, may be used alone although more preferably in admixture with the straight-chain glycols. Copolyesteramides are made by including in the reaction mixture terephthalic, isophthalic or bis-sulphonyl-p-dibenzoic acid, or an acid of formula HOOC-R1-COOH, where R1 is an alkylene group containing 4-8 carbon atoms or esters of such acids. Polyesterification is effected by heating the reactants at 100-300 DEG  C. at atmospheric pressure and in the presence of an ester-interchange catalyst to form the glycol esters of the acids and heating these esters at above 200 DEG  C. under reduced pressure, either in the melt phase or in the form of a powder.  The catalyst may be a metal or a hydride, oxide, alcoholate or salt thereof or a double metal alcoholate or salt, many such catalysts being specified. The preferred catalysts are titanium butoxide and sodium hydrogen titanium ethoxide butoxide together with water as co-catalyst.  The polyesteramides are useful in the manufacture of films and fibres, which may be drawn, and of tubing and the films are useful as photographic film bases.  Examples describe the making of polyesters from bis - (N - p - carbethoxyphenyl) - azelamide, bis - (N - p - carbethoxyphenyl) - suberamide or bis - (N - p - carbethoxyphenyl) - sebacamide and 1,4-butanediol or 1,6-hexanediol.  The polyesteramides of bis-(N-p-carbethoxyphenyl)-adipamide and ethylene glycol, 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol are also referred to.  Specification 824,308 is referred to.