Patent GB-795356-A (GB)
Title: Improvements in and relating to the production of artificial filaments, threads, fibres, bands and the like
Inventor: REEDER FRANK
IPC: D01F4/00
Filed: 1955-07-06
Abstract: Tris (2 : 3-epoxypropyl) amine is prepared by two stages, the intermediate product tris (3-chloro-2-hydroxy propyl) amine being first prepared (a) by the method described by Tauconnier in Comptes Rendues, 1888, Volume 107, pages 115-117, in which epichlorhydrin is subjected, with cooling, to a number of treatments with a stream of dry ammonia gas; or (b) by the addition of an aqueous solution of ammonia to a vigorously stirred mixture of epichlorhydrin and water, the temperature not being allowed to exceed 60 DEG  C.; or (c) by passing ammonia gas into vigorously stirred epichlorhydrin containing 15 per cent by weight of previously prepared tris (3-chloro-2-hydroxy propyl) amines, to promote absorption and reaction, at temperatures below 45 DEG  C.  Tris (2 : 3-epoxypropyl) amine is then obtained (i) by treating tris-(3-chloro-2-hydroxypropyl) amine with an aqueous solution of sodium hydroxide; or (ii) by the addition of powdered sodium hydroxide, or a concentrated aqueous solution of sodium hydroxide, to a warm mixture of the tris-chlorhydrin and methylene chloride; or (iii) by a method similar to (i) carried out in aqueous solution.  N,N1 - bis - (2 : 3 - epoxypropyl) tetra - (3-chloro - 2 - hydroxypropyl) ethylene diammonium chloride is prepared by heating epichlorhydrin with N,N1 - bis - (3 - chloro - 2 - hydroxypropyl) ethylene diamine, prepared by the action of epichlorhydrin on ethylene diamine in methylene chloride solution at room temperature. Methyl tris (2 : 3-epoxypropyl) ammonium methosulphate is prepared by adding a solution of tris-(2 : 3-epoxypropyl) amine in methylene chloride to a solution of dimethyl sulphate in methylene chloride.  A polyepoxide from epichlorhydrin and tetramethylene pentamine is prepared by the addition of tetraethylene pentamine to a mixture of epichlorhydrin and methylene chloride.ALSO:In the production of protein threads by extruding a solution of a protein into an aqueous coagulating bath and hardening the resultant threads in a bath containing formaldehyde and one or more metal salts, the wet properties of the threads are improved by reacting them with a polyepoxy compound, the molecule of which contains at least three epoxy groups.  Examples of suitable epoxy compounds are tris (2:3-epoxypropyl) amine, methyl tris (2:3-epoxypropyl) ammonium methosulphate, the polyepoxy compound obtained by further epoxidation of symmetrical NN1-bis-(2:3-epoxypropyl)-tetra(3 - chloro - 2 - hydroxy propyl) ethylene diammonium chloride, and the poly-epoxide compound obtained by reacting epichlorhydrin and tetraethylene pentamine.  The poly-epoxy compound may be applied to the threads as such, or in the form of a compound which is free from epoxy groups but contains three or more chlorhydrin groups which are converted to epoxy groups under the reaction conditions, or as a compound containing at least one epoxy group and at least one chlorhydrin group which is convertible into an epoxy group on the thread, the total number of epoxy groups after such conversion being at least three.  If the treatment is to be combined with a cyanate treatment as described in Specifications 614,506 and 701,645, [both in Group IV (a)], the latter may be effected before, simultaneously with or after treatment with the epoxy compound.  The threads obtained possess a reduced water imbibition and dyed threads, particularly those dyed with acid levelling dyes, e.g. Azo Geranine 2G or Azo Rubinole 3 G.P, show an improved wash fastness.  The water imbibition is further reduced if treatment is followed by heat treating the dried threads. Specifications 463,043, [Group IV], and 686,117, [Group IV (a)], also are referred to.ALSO:In the production of protein threads by extruding a solution of a protein into an aqueous coagulating bath and hardening the resultant threads in a bath containing formaldehyde and one or more metal salts, the wet properties of the threads are improved by reacting them with a polyepoxy compound, the molecule of which contains at least three epoxy groups.  Examples of suitable epoxy compounds are tris - (2 : 3 - epoxypropyl) amine, methyl tris - (2 : 3 - epoxypropyl) ammonium methosulphate, the poly-epoxy compound obtained by further epoxidation of symmetrical N,N1 - bis - (2 : 3 - epoxypropyl)-tetra - (3 - chloro - 2 - hydroxy - propyl) ethylene di-ammonium chloride, and the poly-epoxide compound obtained by reacting epichlorhydrin and tetraethylene pentamine.  The poly-epoxy compound may be applied to the threads as such, or in the form of a compound which is free from epoxy groups but contains three or more chlorhydrin groups which are converted to epoxy groups under the reaction conditions, or as a compound containing at least one epoxy group and at least one chlorhydrin group which is convertible into an epoxy group on the thread, the total number of epoxy groups after such conversion being at least three.  If the treatment is to be combined with a cyanate treatment as described in Specifications 614,506 and 701,645, the latter may be effected before, simultaneously with or after treatment with the epoxy compound.  The threads obtained possess a reduced water imbibition and dyed threads, particularly those dyed with acidlevelling dyes, e.g. Azo Geranine 2G or Azo Rubinole 3 G.P., show an improved wash fastness.  The water imbibition is further reduced if the treatment is followed by heattreating the dried threads.  Specifications 463,043, [Group IV], and 686,117 also are referred to.