Patent GB-513414-A (GB)
Title: Process for the colouring of organic derivatives of cellulose
IPC: D06P3/34
Filed: 1938-01-07
Abstract: 513,414. Dyeing textiles azo dyes. KODAK, Ltd. Jan. 7, 1938, Nos. 477, 478, 479, 480 and 481. Convention dates, Jan. 14, 1937, and Jan. 23, 1937. [Classes 2 (iii) and 15 (ii)] Colourations fast to light and washing are obtained on organic derivative of cellulose materials by applying thereto or forming therein a nuclear non-sulphonated azo derivative of barbituric acid or a substituted barbituric acid other than 2-imino-3-cyanobarbituric acid. The process of Specification 482,184 is disclaimed. Specified substituted barbituric acids include thiobarbituric, 2- iminobarbituric, 2 - alkyliminobarbituric, 6- iminobarbituric, 6 - iminothiobarbituric, 1 - methyl- or ethyl-barbituric, 1:3-dimethylbarbituric, 1-methyl-3-ethylbarbituric, 1-phenylbarbituric acids and others of the general formulae wherein X represents O, S or NH, Y represents O, NH or NR<1> and R and R<1> represent H, alkyl or non-sulphonated aryl, or wherein X represents O or S, R represents H, alkyl or non-sulphonated aralkyl or aryl and R1 represents alkyl or non-sulphonated aralkyl or aryl, or wherein X represents O or S and R represents H, alkyl or non-sulphonated aralkyl or aryl. The diazo component may be an arylamine or an aminothiazole. Certain of the dyes are obtainable by the process of Specification 513,462. Examples are given of the preparation of the following dyestuffs for use in the process : (1) 2:4-dinitroaniline#barbituric acid, (2) 4- aminoacetanilide #barbituric acid, (3) 2-nitroaniline# cresidine# barbituric acid, (4) 2-#- hydroxyphenetidine# barbituric acid, (5) 2- #-methoxyphenetidine# barbituric acid, (6) 2- aminodiphenyl etherbarbituric acid, (7) 2-anisidine# barbituric acid, (8) 6-methoxy-1- aminobenzothiazole# barbituric or thiobarbituric acid, (9) 2-aminothiazole# thiobarbituric acid, (10) aniline# 1-methyl-barbituric or thiobarbituric acid, (11) 2-anisidine# 1:3-dimethylbarbituric acid or -thiobarbituric acid, (12) 2- phenetidine# 1-methyl-3-ethyl - barbituric or -thiobarbituric acid, (13) 2-#-hydroxyphenetidine# 1-phenyl-barbituric or -thiobarbituric acid, (14) 2-#-methoxyphenetidine# 1-(4<1>-methoxy)phenyl-3-#-hydroxyethyl-barbituric or - thiobarbituric acid, (15) 3-methoxy-4-aminophenyl methyl ketone# 1-benzyl-barbituric or - thiobarbituric acid, (16) 2-nitraniline# 1-ethylbarbituric or -thiobarbituric acid, (17) 2-nitro- 4 - chloraniline# 1:3 - dimethyl - barbituric or - thiobarbituric acid, (18) 2-nitro-4-methylaniline - 1-benzyl-3-#-hydroxyethyl-barbituric or -thiobarbituric acid, (19) 4-amino-3:2<1>-dinitroazobenzene# 1-methyl-3-ethylthiobarbituric acid, (20) 2:4-dinitroaniline# 1:3-di-#-hydroxyethylthiobarbituric acid. Tables are also given showing the shades obtainable on cellulose acetate artificial silk with the dyestuffs from numerous combinations of components. In examples of the dyeing process, (A) a cellulose acetate taffeta is passed twice through an aqueous dispersion at 100‹F. of 2- or 4-anisidine # barbituric acid, whereupon the temperature is raised to 200‹F. and dyeing continued for 1 hour to obtain a greenish yellow shade, fast to light; (B) a mixed fabric of cellulose acetate and viscose yarns is similarly dyed with 4- phenetidine# thiobarbituric acid, dispersed with soap or oleylglyceryl sulphate ; the cellulose acetate only is dyed orange yellow ; the viscose may be coloured by adding Chloramine red 3B or Direct blue 2B to the bath ; (C) cellulose acetate artificial silk taffeta or thread is entered into an aqueous soap dispersion at 45- 55‹C. of 2-anisidine# 6-iminobarbituric acid, whereupon the temperature is raised to 80- 85‹C. and dyeing continued for several hours to obtain a greenish yellow shade ; (D) similar material is similarly dyed with 2-phenetidine# 2-iminobarbituric acid ; (E), (F) and (G) cellulose acetate artificial silk yarn or fabric as in (C) with (E) 2-anisidine# 1:3-dimethylbarbituric acid, (F) 2-phenetidine# 1-methyl-3- ethylbarbituric acid, (G) 2-nitraniline# 1-ethylthiobarbituric acid. 1-Methyl 3 - ethylbarbituric acid, 1 -benzylbarbituric acid 1-#-hydroxyethylbarbituric acid, 1-methyl-3-#-hydroxyethyrbarbituric acid, 1:3-di- (#-hydroxyethyl) barbituric acid, 1-benzyl-3- methylbarbituric acid, 1-benzyl-3-#-hydroxyethylbarbituric acid and 1-benzyl-3-#-methoxyethylbarbituric acid are obtained by condensing the correspondingly substituted ureas with diethyl malonate. The Specification as open to inspection under Sect. 91 comprises also the manufacture of certain of the dyestuffs and of analogous sulphonated dyestuffs for cotton,. silk and wool. This subject-matter is covered by Specification 513,462 and does not appear in the present Specification as accepted.