Patent GB-832400-A (GB)
Title: New anthraquinonoid dyestuffs
Inventor: HESLOP ROBERT NORMAN
IPC: G05B19/12
Filed: 1957-07-22
Abstract: The invention comprises dyestuffs which in the form of their free acids are of the formula <FORM:0832400/IV(c)/1> where X is a bridging group containing at least one anionic solubilizing group, Y is a chlorine or bromine atom, Q is an oxygen or sulphur atom or -NR1-, and R and R1 may be the same or different and R is hydrogen or a hydrocarbon or substituted hydrocarbon radical having no dyestuff character and R1 is hydrogen, alkyl or substituted alkyl, and a process for making the dyestuffs by interacting a cyanuric chloride or bromide on the one hand with a compound of the formula <FORM:0832400/IV(c)/2> and on the other hand with a compound of the formula H-Q-R, under such conditions that the product still contains a halogen atom attached to the triazine ring.  Hydrocarbon or substituted hydrocarbon radicals represented by R include methyl, beta-ethoxyethyl, cyclohexyl, benzyl, phenyl, tolyl, chlorophenyl and sulphophenyl, radicals represented by R1 include methyl and beta-ethoxyethyl, and R and R1 may be joined to form an N-morpholino radical.  Bridging groups represented by X include phenylene and diphenylene radicals and the radical -C6H4- -N = N-C6H4- each of which is substituted by at least one anionic water-solubilizing groups such as sulphonic acid or carboxylic acid and may be further substituted by methyl, methoxy or chloro groups. Compounds of the formula H-Q-R include methanol, ethanol, iso-butanol, octanol, beta-ethoxyethanol, cyclohexanol, benzyl alcohol, phenylethyl alcohol, phenol, o-, m- and p-cresols, xylenols, chlorophenols, sulphophenols, dialkylaminophenols, sulphonaphthols, ammonia, methylamine, diethylamine, hydroxyethylamine, taurine, glycine, benzylamine, cyclohexylamine, aniline, toluidine, chloroaniline, anisidine, aminoacetanilide, orthanilic, metanilic and sulphanilic acids, thiophenol, thiocresol and p-sulphothiophenol.  The reaction may be conducted at between 15 DEG  and 50 DEG  C. at a pH between 4 and 7 in aqueous medium in the presence of an acid-binding agent. The dyes colour cellulose textiles, wool, silk, and fibres of ardein, casein, polyamide or modified polyacrylonitrile greenish blue and green shades.  In examples: 1-amino-4-(41-aminoanilino) anthraquinone - 2 : 31 : 5 - trisulphonic acid is reacted with cyanuric chloride; and (2) ammonia, (5) sodium 4-acetylamino phenate, (6) phenol, (7) thio - p - cresol, (8) o - cresol, (9) 4 - methoxyphenol, (10) 3 - (N : N - diethylamino)-phenol and (11) 3-sulphoaniline, or with (1) 2 : 4 - dichloro - 6 - methoxy - s - triazine; in further examples, (3) sodium 1-amino-4-(41-[411 - aminostyryl]anilino) - anthraquinone-2 : 211 : 31 : 5 - tetrasulphonate is reacted with 2 - betamethoxyethoxy - 4 : 6 - dichloro - s-triazine: (4) sodium 1 - amino - 4 - (41 - [411-aminophenyl] - anilino) - anthraquinone - 2 : 311 : 5-trisulphonate is reacted with cyanuric chloride and sodium metanilate; (12) 1-amino-4-(41-aminoanilino) anthraquinone - 2 : 31 : 6 - trisulphonic acid is reacted with cyanuric chloride and methanol; and (13) 1 - amino - 4 - (41-[411 - aminobenzeneazo] anilino) anthraquinone - 2 : 211 : 5 - tri sulphonic acid is reacted with cyanuric chloride and 3-sulphoaniline.  The Provisional Specification also relates to dyestuffs of the above general formula where Q is a direct linkage and where R may be a hydrocarbon or substituted hydrocarbon radical in general. Specification 798,121 also is referred to.