Patent GB-542213-A (GB)
Title: Dyestuffs derived from 2-amino-3-naphthoic acid
IPC: C09B29/32
Filed: 1940-04-26
Abstract: 542,213. Dyes. COMPAGNIE NATIONALE DE MATIERES COLORANTES ET MANUFACTURES DE PRODUITS CHIMIQUES DU NORD REUNIES ETABLISSEMENTS KUHLMANN. April 26, 1940, No. 7506. Convention date, April 27, 1939. [Classes 2 (ii), 2 (iii) and 15 (ii)] Monoa o dyes substantially insoluble in water are obtained by coupling diazotized 2-amino-3- naphthoic acid with an arylamide of an acylacetic acid and may be treated with agents yielding metal, e.g. chromium, nickel, cobalt, iron or copper, to obtain metalliferous complexes suitable for colouring cellulosic lacquers, paints and cellulose ester solutions from which pellicles and fibres are formed. By using sulphonated components in preparing the dyestuffs, or by sulphonating the dyestuffs, water-soluble products are obtained which are suitable for dyeing or printing protein fibres, e.g. of wool, silk, leather or casein, or animalized cellulosic fibres, with fixation of the dyeings by afterchroming, for colouring lacquers, paints, printing inks, plastic masses, paper, cosmetics, etc., and for the manufacture of lakes. These sulphonated dyestuffs may be treated with an agent yielding metal, e.g. chromium, or the aoove metal complexes of the unsulphonated dyestuffs may be sulphonated to obtain, for example, primary or secondary chromium complexes according to whether the chroming is effected in a neutral or an acid medium, such complexes being suitable for dyeing or printing animal fibres, especially leather, or, in the form of the free acids, for colouring lacquers or solutions from which films or pellicles are formed. Examples (1) to (6) relate to the manufacture of (1) the dyestuff, 2-amino-3-naphthoic acid # the anilide of acetoacetic acid, and its secondary chromium complex ; (2) the dyestuff, 2-amino- 3-naphthoic monosulphonic acid # the ptoluidide of acetoacetic acid, which dyes wool a green-yellow, scarcely cnanged in shade and made fast to rubbing, fulling and light on afterchroming ; (3) the corresponding dyestuff having as coupling component 1-acetoacetylamino- 2:4-dimetbylbenzene, which dyes chromed leather intense fast greenish-yellow shades (4) 2-amino-3-naphthoic disulphonic acid # the o-anisidide of acetoacetic acid, which dyes animal fibres green-yellow, made fast to fulling and to light by after-chroming ; (5) and (6) the secondary chromium complexes of the dyestuffs in (2) and (4) repectively, which dye wool fast yellow-green shades. Example (7) relates to the colouring of a nitrocellulose lacquer an intense yellow-green, fast to light and to offsetting, with the chromium complex of (1). Example (8) relates to the dyeing of wool with the dyestuff of (2) from a boiling aqueous bath containing ammonium sulphate and acetic acid witn a later addition of sulphuric acid, and to after-chroming of the dyeing. Example (9) relates to the dyeing of chromed leather with the dyestuff of (3) from an aqueous bath. Example (10) relates to the treatment of the dyestuff of (2), (3) or (4) with blanc fixe, aluminium sulphate and barium chloride to obtain a lake. A table is also given showing the uses of dyestuffs from various components and of their chromium compounds, additional coupling components specified being acetoacetylcresidine and acetoacetylaminohydroquinone diethyl ether. Specifications 12249/15, 15127/15, 116,530, 275,307, [all in Class 2 (iii)], and 446,820 are referred to. 2- Amino- 3-naphthoic mono- and di-sulphonic acids are obtained by sulphonation of 2-amino- 3-naphthoic acid with sulphuric acid monohydrate and oleum respectively. The Specification as open to inspection under Sect. 91 comprises also the manufacture and similar use of the corresponding dyestuffs and their sulphonated and/or metallized derivatives, from diazotized 2-amino-3- naphthoic acid and any coupling component, other than 2:5:7-aminonaphtholsulphonic acid, coupling in o-position to an amino or hydroxy group, e.g. a #-diketone, a pyrazolone, a phenol or naphthol, an aromatic diamine, a naphthylamine or an aminonaphthol. Additional examples relate to the manufacture of the dyestuffs, 2-amino-3-naphthoic acid # resorcinol and its secondary chromium and cobalt complexes, 2-amino-3-naphthoic acid # 2- naphthol, its sulphonation product and its secondary chromium complex, 2-amino-3-napbthoic acid # 1-(4<SP>1</SP>-sulpho)phenyl-3-methyl-5- pyrazolone and its secondary chromium complex, 2-amino-3-naphthoic mono- or disulphonic acid # 1-phenyl-3-methyl-5-pyrazolone and the secondary chromium complex of the monosulphonated product 2-amino-3- naphthoic monosulphonic acid # resorcinol, 2-naphthol, p-cresol, 1:3-phenylenedianiine, 1:4- naphthol-sulphonic acid, 2-naphthylamine or 1:8:4-aminonaphtholsulphonic acid, 2-amino-3- naphthoic acid # 2:6-naphtholsulphonic acid, the copper complex of 2-amino-3-naphthoic. monosulphonic acid # 1:3-phenylenediamine. An example is also given of the dyeing of wool with the secondary chromium complex of the dyestuff, 2-amino-3-naphthoic acid # 1-(4<SP>1</SP>-sulpho) phenyl-3-methyl-5-pyrazolone from a boiling aqueous bath containing ammonium sulphate and sulphuric acid. In a table showing the uses of dyestuffs from various components and their chromium compounds, addi ional specified coupling components are 1-(2<SP>1</SP>-chloro-5<SP>1</SP>-sulpho) phenyl - 3 - methyl - 5 - pyrazolone and 1:3- phenylenediamine sulphonic acid. This subject-matter does not appear in the Specification as accepted.