Patent GB-1117110-A (GB)
Title: Improvements relating to acid anthraquinone dyestuffs and their use
IPC: C09B1/30
Filed: 1965-12-22
Abstract: The invention comprises acid anthraquinone dyestuffs of the formula <FORM:1117110/C4-C5/1> wherein R1 is a secondary alkyl or cycloalkyl group, R12 is an aralkyl group which may be ring-substituted by C1-C4 alkyl or alkoxy, or halogen and it can be monovalent when R13 is aralkyl, otherwise it is polyvalent; R13 is an alkyl, cycloalkyl or a monovalent or polyvalent aralkyl group optionally ring-substituted by C1-C4 alkyl or alkoxy, or halogens; R4 is H or C1-C4 alkyl, A is an alkenyl group optionally containing at least one substituent which can be split as an ion, which alkenyl radical can be further substituted or it represents an alkyl group containing at least one substituent which can be split off as an ion, which alkyl group may be further substituted, m and n each represents 1 or 2, and in so far as R12 and R13 contain a sulphonic acid group and a group <FORM:1117110/C4-C5/2> they are linked to these groups by a ring carbon atom.  They may be obtained by (1) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/3> wherein X is a Cl, Br, OH, C1-C4 alkoxy, NO2 or amino group, with an aralkylamine containing at least two exchangeable hydrogen atoms in the aryl moiety, of the formula <FORM:1117110/C4-C5/4> wherein R2 is an aralkyl group optionally ring-substituted by C1-C4 alkyl or alkoxy, or halogens and R3 is an alkyl group, a cycloalkyl group or an aralkyl group optionally ring substituted by C1-C4 alkyl or alkoxy or halogens, to form the corresponding 1-sec. alkylamino- or 1 - cycloalkylamino - 4 - aralkylaminoanthraquinone compound and, in any order, condensing this with n mol. of sulphonating agent and with m mol. of a compound of the formula <FORM:1117110/C4-C5/5> (2) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/6> wherein Y is an acyl radical, with an aralkylamine of Formula II to form the corresponding 1 - (N - sec. alkyl - N - acylamino)- or 1 - (N-cycloalkyl - N - acylamino) - 4 - aralkylamino-anthraquinone compound and, in any order, saponifying and condensing this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a reactive functional derivative thereof; (3) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/7> wherein W is a Cl, Br, OH, C1- 4 alkoxy, NO2 or amino group with a sec. alkylamine or a cycloalkylamine of the formula <FORM:1117110/C4-C5/8> to form the corresponding 1-sec. alkylamino- or 1 cycloakylamino - 4 - aralkylamino - anthraquinone compound and, in any order, condensing this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a functional derivative thereof; and (4) condensing an anthraquinone compound of the formula <FORM:1117110/C4-C5/9> with a sec. alkylamine or a cycloalkylamine of Formula VII to form the corresponding 1-sec. alkylamino- or 1 - cycloalkylamino - 4 - (N - aralkyl - N - acylamino) - anthraquinone compound and, in any order, saponifying and reacting this with n mol. of a sulphonifying and reacting this with n mol. of a sulphonating agent and m mol. of a compound of Formula III or a functional derivative thereof. Specified acyl groups for Y are carbacyl groups, e.g. alkanoyl or aroyl radicals, alkyl- or aryl-sulphonyl radicals.  Specified substituents which may be split off as an ion, i.e. cation or anion, are halogens, alcoholic hudroxyl esterified with sulphuric acid or with aliphatic or aromatic sulphonic acid, or the groups R-O-, R-S-and R-SO2, wherein R is an organic radical; quaternary ammonium groups, the group <FORM:1117110/C4-C5/100> Examples are given for the production of the dyes.  They may be used for dyeing or printing natural or synthetic polymide fibres blue shades, and also for the dyeing of cellulos materials.