Patent GB-675665-A (GB)
Title: Improvements in and relating to the production of polymeric compounds
IPC: C08G65/22
Filed: 1949-03-02
Abstract: Polymeric compounds, capable of being drawn into fibres, are produced by reacting in substantially equimolecular proportions epichlorhydrin and an amine of formula R.NH2, where R is an aryl or aralkyl group containing only carbon and hydrogen, together with alkali in an amount at least equivalent to the chlorine content of the epichlorhydrin.  Specified amines are aniline, benzylamine and paratoluidine or mixtures thereof.  The amine may be replaced in part by a carboxyl substituted primary amine (e.g. para-amino benzoic acid) or by a dihydric phenol in which the carbon atoms linked to the hydroxyl groups are separated by at least one other carbon atom (e.g. hydroquinone).  The reaction may be performed (a) by heating the amine, epichlorhydrin and alkali together; (b) by reacting epichlorhydrin and the amine to form a compound R.NH.CH(OH).CH2Cl which is heated with alkali to form a compound <FORM:0675665/IV (a)/1> which may or may not be isolated prior to heating it to polymerize it; (c) by reacting epichlorhydrin, the dihydric phenol and alkali to form a bisglycidyl ether which is then heated with the amine.  In examples: (1) aniline (1 mol.) and epichlorhydrin (1 mol.) are heated together and the product is dissolved in alcohol and refluxed with caustic soda (1.15 mol.); (2) aniline (1 mol.), epichlorhydrin (1 mol.) and sodium carbonate (0.56 mol.) are refluxed in presence of water and alcohol.  The product is dissolved in dilute hydrochloric acid and precipitated with aqueous caustic soda solution; (3) aniline (1 mol.) and epichlorhydrin (1 mol.) are allowed to stand at room temperature and the product refluxed with sodium bicarbonate (1.1 mol.) in presence of water and alcohol; (4) aniline (1 mol.), epichlorhydrin (1 mol.), water and alcohol are refluxed, caustic soda (1.1 mol.) added and the mixture refluxed; (5) benzylamine (1 mol.), epichlorhydrin (1 mol.) and alcohol are mixed, sodium carbonate (0.56 mol.) added and the mixture refluxed; (6) aniline (1 mol.), epichlorhydrin (1.1 mol.), and alcohol are refluxed, sufficient alcoholic potash added to precipitate all the potassium chloride, the alcohol and excess epichlorhydrin removed by distillation, the residue distilled at 2 mm. of mercury and the distillate heated to yield a polymer soluble in hot dilute aqueous mineral acid; (7) aniline (1 mol.), epichlorhydrin (1 mol.), sodium bicarbonate (1.1 mol.) and water are refluxed; (8) aniline (1 mol.), hydroquinone bis-glycidyl ether (1 mol.) alcohol, and aqueous caustic soda solution are refluxed.  Specifications 438,523, 628,821, 652,024 and 652,030 are referred to.ALSO:Compounds of formula <FORM:0675665/IV (b)/1> where R is an aryl or aralkyl hydrocarbon group, are produced by reacting a primary amine of formula R.NH2 with epichlorhydrin.  Specified primary amines are aniline, benzylamine and paratoluidine.  The compounds of formula NHR.CH2.CH(OH).CH2Cl react with alkalies to give compounds of formula <FORM:0675665/IV (b)/2> The latter compounds polymerize on heating (see Group IV (a)). Specification 438,523 is referred to.