Patent GB-535888-A (GB)
Abstract: 535,888. Textile treating agents. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 30, 1939, Nos. 15872 and 15873. Convention date, May 3], 1938, and May 23, 1939. [Classes 2 (iii) and 15 (ii)] In a process for improving fibrous materials, particularly textile, the materials are treated with a compound of the general formula R 1 -X-CH 2 -R 2   where R 1  is an aliphatic residue containing at least one reactive halogen atom and at most 9 carbon atoms, X is an O atom, which may be in the form of an ester-like bridge, or an -NR- bridge, which may be in the form of an amidelike residue, R 2  is a residue containing or consisting of quaternary ammonium groups or of radicles of thioureas in salt form, which residue is united to the CH 2  group through a hetero atom (O, S or N) and R is hydrogen or a hydrocarbon residue, and the treated material is heated. Cellulose materials thereby acquire affinity for acid wool dyes, or the fastness of dyeings is improved by the treatment. Compounds of the general formula in which X represents the N-atom of a -CO-NH-group may be made by reacting carboxylic acid amides, such as chloracetamide, #-chloropropionic and amide, α-bromobutyric acid amide or chlorosuccinic acid diamide with formaldehyde and a salt of a tertiary amine, e.g. trimethylamine, triethylamine, dimethylcyclohexylamine, dimethylaniline, pyridine, a C-alkylpyridine or quinoline. The amides may also be converted into the halogenmethyl derivative by reaction with formaldehyde and hydrogen halide and the product reacted with the tertiary amine. Similar products may be obtained from compounds in which X represents the N-atom of a - O-CO-NR 4 - or -N(COOR 4 )- group, where R 4  is a hydrogen atom or aliphatic residue. Products of the general formula in which R 2  is a thiourea residue may be obtained from N- methylolamides of aliphatic carboxylic acids which contain at least one halogen atom in the aliphatic residue, by the process described in Specification 524,068. Products in which X = O may be obtained by reacting thiourea with α- halogenmethylethers of alcohols containing a reactive halogen atom. Products of the general formula which may be used also include those in which R 2  represents the grouping -V-R 5 -W, where V is an O-atom, if desired in the form of an ester-like bridge, an S-atom, or the N-atom of a -CO-NR- group, R 5  is an organic residue, and W is a quaternary ammonium group or a radical of a thiourea in salt form. Such products may be made by the process described in Specification 523,396 from parent materials in which the residue R 1  contains a halogen atom. In carrying the invention into effect, the products of the general formula are caused to act on textile material by impregnating the material with a solution or dispersion of the product, if desired in the presence of a weak acid or acid salt. The subsequent heat treatment is carried out preferably at a temperature of 115-120‹ C. In examples (1) cotton is impregnated with (a) #-chlorethoxymethylpyridinium chloride or (b) chloracetaminomethylpyridinium chloride or α-bromovalerianaminomethylpyridinium chloride, or (c) the condensation product from chloromethyl-#-chlorethyl ether and thiourea, or (d) the condensation product from 2-chloromethoxy-1:3-dichloropropane and thiourea ; the treated material is then squeezed, dried and heated, when it acquires a pronounced affinity for acid wool dyes, and (2) a cotton fabric dyed with Direct Fast Violet 2RL is treated with a solution of . #-chlorethoxymetbylpyridinium chloride in presence of sodium acetate, squeezed, dried and heated ; the dyeing has a pronounced fastness to washing. The Specification as open to inspection under Sect. 91 comprises also the treatment of fibrous materials with compounds of the general formula R 1 -X-CH 2 -R 2  in which R 1  is any organic residue having at least one reactive group, X is an -O-, -S-, or -NR- bridge, and R 2  is any residue which determines or enhances solubility in water and which is united with the -CH  2 - group through a hetero-atom. The treated material may be subjected to a further treatment which converts the reactive group in the residue R 1  into a basic group. A large number of additional compounds of the general formula is specified, and numerous additional examples are given, some of which now appear in Specification 533,073. This subject-matter does not appear in the Specification as accepted.