Patent GB-659678-A (GB)
Title: Improvements in or relating to polyamide resins
IPC: C08G69/34
Filed: 1949-08-17
Abstract: Polyamides soluble in methanol and ethanol are prepared by condensing a di-primary amine in which one amine group is directly linked to a saturated tertiary carbon atom with the dimer of an olefinically unsaturated monocarboxylic acid containing 16 to 22 carbon atoms and derived from a natural oil or with a reactive derivative of such a dimer.  Specified diamines are 1 : 2-diamino-2-methyl propane, 2 : 3-diamino-2-methyl butane, 2 : 4-diamino-2-methyl pentane, 2 : 3-diamino-2 : 3-dimethylbutane, 2 : 5 - diamino - 2 : 5 - dimethylhexane, 3 : 4 - diamino - 3 : 4 - dimethylhexane, 2 : 6 - diamino - 2 : 6 - dimethylheptane, 2 : 7-diamino-2 : 7-dimethyloctane and a mixture of 3 : 5 - diamino - 3 : 4 - dimethylhexane and 3 : 5 - diamino - 3 - methylheptane. Suitable diamines may be prepared by hydrogenating aldehyde-ketone condensates (see Group IV (b)). Specified acids are dimers of mono-olefinic acids, e.g. palmitoleic, oleic, petroselenic, vaccenic, gadoleic, cetoleic, or erucic and dimers of polyene acids, e.g. hiragonic, linoleic, elaeostearic, licanic, arachidonic, and clupudonic derived for example from linseed, soy bean, corn, cotton seed, hemp seed, kapok seed, herring, perilla, poppy seed, pilchard, whale, menhaden, mustard, peanut, rape seed, salmon, sardine, walnut, dehydrated castor, rubber seed, safflower, sesame, tung or oiticica oils.  The dimerized acids may be mixed with other dicarboxylic acids or anhydrides, e.g. succinic, adipic or sebacic acids or with fatty acids, e.g. stearic, oleic and linoleic.  In examples (1) and (2) dimerized linseed oil, 2 : 4-diamino-2-methyl pentane and xylene are heated in a current of natural gas or nitrogen; (3) polymerized cotton seed oil fatty acid is heated with 2 : 4-diamino-2-methyl pentane in a current of nitrogen; (4) the polymerized methyl ester of soy bean fatty acids is heated with 2 : 4-diamino-2-methyl pentane in a current of nitrogen; (5) the polyamide of example (2) and chlorinated rubber are dissolved in a mixture of methyl isobutyl carbinol and toluene to form a surface coating composition.  The polyamides may be used to plasticize nitro-cellulose, cellulose acetate, polyvinyl butyrol and copolymers of vinyl chloride and vinyl acetate and may be heated in a molecular still to produce super-polyamides.  U.S.A. Specifications 2,379,413 and 2,071,250 are referred to.ALSO:Di-primary aliphatic amines are prepared by hydrogenating a ketone-ammonia condensate.  In an example acetone and ammonia are heated to 30-40 DEG  C. in the presence of hydrochloric acid to form 2 : 2 : 4 : 4 : 6-pentamethyltetrahydropyrimidine which is distilled out and reacted at 140-150 DEG  C. with liquid ammonia and hydrogen at 500-1500 pounds per square inch in the presence of Raney nickel to give 2 : 4-diamino-2-methyl pentane.  Methyl ethyl ketone similarly reacts to give 3 : 5-diamino-3 : 4 - dimethylhexane and 3 : 5 - diamino - 3 - methyl-heptane.  Di-carboxylic acids having 32-44 carbon atoms are prepared by dimerizing an olefinically unsaturated aliphatic monocarboxylic acid derived from a natural oil and containing 16-22 carbon atoms or a reactive derivative of such an unsaturated acid. In examples: (1) monoolefinic acids (many specified), or their methyl esters, are heated in the presence of a boron trifluoride, aluminium chloride or stannic chloride catalyst, the catalyst is washed out and unchanged monomer distilled out and the dimer extracted with, e.g., alcohols, ketones, nitriles, or lower paraffins and preferably a mixture of amyl alcohol and acetonitrile; (2) methyl esters of polyene acids (many specified) are heated at 300 DEG  C. under a carbon dioxide or nitrogen atmosphere (see Industrial and Engineering Chemistry, Vol. 32, pp. 802-809), unreacted material is distilled out and the residue saponified by sodium hydroxide and acidified with a mineral acid; (3) polyene acids (many specified) are heated at 330-360 DEG  C. under 85-400 pounds per square inch steam pressure. The amines and acids may be condensed together to polyamides (see Group IV (a)].