US 4,336,377 A · Basic dioxazine compounds

Abstract

Novel dioxazine compounds of the formula ##STR1## in which Z is a basic group, which can be quaternized, Y is an anionic group and X and X.sub.1 independently of one another are identical or different substituents from the category comprising: hydrogen, halogen, CN, substituted or unsubstituted alkyl (C.sub.1 -C.sub.4); substituted or unsubstituted phenyl; NHCOR.sub.1 in which R.sub.1 is alkyl (C.sub.1 -C.sub.4), cycloalkyl, substituted or unsubstituted aryl or a heterocyclic radical; and OCOR.sub.2 in which R.sub.2 is substituted or unsubstituted alkyl (C.sub.1 -C.sub.4) or cycloalkyl; or X and X.sub.1 are the group ##STR2## in which R.sub.4 and R.sub.5 independently of one another are: hydrogen, substituted or unsubstituted alkyl (C.sub.1 -C.sub.4), cycloalkyl or aryl, or R.sub.4 together with R.sub.5 and with the inclusion of the N atom forms a heterocyclic ring, or X and X.sub.1 are the group COOR.sub.6, in which R.sub.6 is hydrogen, substituted or unsubstituted alkyl or cycloalkyl; n is a number from 1 to 4 and m is a number from 0 to 2, with the proviso that the number m is smaller than n, and in which the benzo radicals A and A.sub.1 can be identical or different and can have one or more further substituents, their preparation and their use as dyes, in particular for dyeing and printing natural and regenerated cellulose materials without the addition of salt, are described.

A dioxazine compound of the formula I ##STR67## wherein Z is (a) a basic group of the formula ##STR68## wherein T.sub.1 is hydrogen;

C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH;
cyclohexyl which is unsubstituted or substituted by 1-3 methyl groups;
or phenyl;
T.sub.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl;
or T.sub.1 and T.sub.2, together with the nitrogen atom to which they are attached, form a pyrrolidine, pyridine, morpholine or piperazine ring;
and W is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH or C.sub.1 -C.sub.4 alkoxy;
or (b) a cationic group of the formula
--CH.sub.2 --NH--CO-alkylene(C.sub.1 -C.sub.4)-K.sup..sym. A.sup..crclbar.(i)
in which K.sup..sym. is a radical of the formula ##STR69## wherein R.sub.7 and R.sub.8, each independently of the other, is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH, carbamoyl or cyano, or R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a pyrrolidine, piperidine or morpholine ring;
R.sub.9 and R.sub.10 are H or C.sub.1 -C.sub.4 alkyl;
or R.sub.7 and R.sub.9 and R.sub.8 and R.sub.10 together with the nitrogen atoms to which they are attached, form a 1,2-diazabicyclo-(3.3.0)-octane ring system;
R.sub.11 is H or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH;
R.sub.12 and R.sub.13, each independently of the other, is hydrogen, phenyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH, carbamoyl or NH.sub.2 ;
or R.sub.11 and R.sub.12, together with the nitrogen atom to which they are attached, form a piperadine, pyrrolidine or morpholine ring;
or R.sub.11, R.sub.12 and R.sub.13, together with the nitrogen atom to which they are attached, form a pyridine ring which is unsubstituted or substituted by methyl, OH, NH.sub.2, carboxy or CN or is annulated to form a quinoline radical;
or R.sub.11, R.sub.12 and R.sub.13, together with the nitrogen atom to which there are attached, form a 1,4-diazabicyclo-(2.2.2.)-octane ring system;
or Z is a cationic group of the formula ##STR70## wherein alkylene is an alkylene bridge which can be interrupted by --O--, --S--, --NH-- or ##STR71## R.sub.14 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.15 and R.sub.17, each independently of the other, is C.sub.1 -C.sub.4 alkyl;
R.sub.16 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NH.sub.2 ;
or R.sub.15 and R.sub.16 together with the nitrogen to which they are attached is pyridinium;
A.sup.- is an anion;
Y is an anionic group;
each of X and X.sub.1, independently of the other, is H;
halogen;
CN;
C.sub.1 -C.sub.4 alkyl;
phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or halogen;
NHCOR.sub.1 wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, cyclohexyl, aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or halogen, or R.sub.1 is a heterocycle selected from the group consisting of furane, thiophene, pyridine, quinoline, phenylthiazole and phenyltriazole;
OCOR.sub.2 wherein R.sub.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by phenyl, or R.sub.2 is cyclohexyl;
##STR72## wherein R.sub.4 and R.sub.5, each independently of the other, is hydrogen, cyclohexyl, aryl, C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by phenyl, ##STR73## wherein T.sub.1, T.sub.2, R.sub.15, R.sub.16 and R.sub.17 are as defined above, or R.sub.4 and R.sub.5, together with the nitrogen atom to which they are attached, form a pyrrolidine, piperidine or morpholine ring;
or COOR.sub.6 wherein R.sub.6 is hydrogen, cyclohexyl or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by OH or phenyl;
each of the benzene radicals A and A.sub.1, independently of the other, is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen;
CN;
C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by phenyl;
phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
COOH;
NO.sub.2 ;
NH.sub.2 ;
mono- or di-(C.sub.1 -C.sub.4)-alkyl amino;
NHCO--C.sub.6 H.sub.5 ;
NHCOR.sub.18 where R.sub.18 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by phenyl, C.sub.1 -C.sub.4 alkoxy, cyclohexyl or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, NO.sub.2 or CN;
SCN;
benzothiazole which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, OH or phenyl;
phenoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl;
NHR.sub.19 wherein R.sub.19 is H or phenyl which is unsubstituted or fused with a hetero ring to form a benzoxazole, benzthiazole or benzimidazole;
C.sub.1 -C.sub.4 alkylsulfonyl;
or CONHR.sub.20, wherein R.sub.20 is phenyl which is unsubstituted or substituted by halogen, phenyl or C.sub.1 -C.sub.4 alkyl;
n is a number from 1 to 4 and m a number from 0 to 2, with the proviso that number m is small than n.

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Basic dioxazine compounds

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Basic dioxazine compounds

Life of this patent

Abstract

Claims10