Water soluble reactive axodyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule

Claim 2

A reactive dyestuff of the formula ##STR52## wherein D stands for the radical of a water-soluble sulfonic acid containing azo dyestuff; R stands for hydrogen or lower alkyl; Q stands for CO, SO 2 , CH 2 , CH 2 CO, ##STR53## n stands for 0 or 1, --(Q) n --N(R) being linked with a nuclear aromatic carbon atom of D; R 1 stands for NH 2 , hydroxy; mercapto; methyl; trichloromethyl; phenyl; methylphenyl; chlorophenyl; sulfophenyl; hydroxyphenyl; morpholino; piperidino; hydrazino; N-methylhydrazino; N--(R 10 )--R'; wherein R 10 stands for lower alkyl, cyano lower alkyl, hydroxy lower alkyl, phenyl or phenyl substituted by a member selected from the class consisting of chlorine, bromine, lower alkyl, lower alkoxy, sulfo, and carboxy; and R' stands for hydrogen, lower alkyl, hydroxy lower alkyl, cyano lower alkyl or benzyl; OR 11 wherein R 11 stands for phenyl, sulfophenyl, lower alkyl or lower alkoxy substituted lower alkyl; or SR 12 wherein R 12 stands for lower alkyl, hydroxy lower alkyl, phenyl, chlorophenyl, sulfophenyl; and F is fluoro.

Claim 3

A water-soluble reactive dyestuff of claim 1 of the formula ##STR54## wherein A stands for the radical ##STR55## wherein R' 1 is NH 2 ; lower alkyl amino; cyanoloweralkylamino, hydroxy lower alkyl amino; benzylamino; phenylamino; sulfophenylamino; chlorophenylamino; gromophenylamino; lower alkyl phenylamino; lower alkoxy phenylamino; carboxy phenylamino; N,N di lower alkylamino; N-lower alkyl-N-cyano lower alkylamino; N-lower alkyl-N-hydroxy lower alkylamino; N-lower alkyl-N-benzylamino; N-lower alkyl-N-phenylamino; N-lower alkyl-N-sulfophenylamino; N-lower alkyl-N-chlorophenylamino; N-lower alkyl N-bromophenyl amino; N-lower alkyl-N-lower alkoxy phenylamino; N lower alkyl-N-carboxy phenylamino; N,N-dihydroxy lower alkylamino; N-hydroxy lower alkyl-N-cyano lower alkylamino; N-hydroxy lower alkyl-N-benzylamino; N-hydroxy lower alkyl-N-phenyl amino; N-hydroxy lower alkyl-N-sulfophenylamino; N-hydroxy lower alkyl-N-chlorophenylamino; N-hydroxy lower alkyl-N-lower alkyl phenylamino; N-hydroxy lower alkyl N-lower alkoxy phenylamino; N-hydroxy lower alkyl-N-carboxy lower alkylamino; N,N-dicyano lower alkyl amino; N-cyano lower alkyl-N-benzylamino; N-cyano lower alkyl-N-phenylamino; N-cyano lower alkyl-N-sulfophenylamino; N-cyano lower alkyl-N-chlorophenylamino; N-cyano lower alkyl-N-bromophenylamino; N-cyano lower alkyl-N-lower alkoxy phenylamino; N-cyano lower alkyl-N-carboxyphenylamino; N,N-dibenzylamino; N-benzyl-N-phenylamino; N-benzyl-N-sulfophenylamino; N-benzyl-N-chlorophenylamino; N-benzyl-N-bromophenylamino; N-benzyl-N-lower alkoxy phenylamino; N-benzyl-N-carboxy phenylamino; lower alkoxy, or lower alkoxy substituted lower alkoxy; F stands for fluro; R' stands for hydrogen or methyl; (o) indicates the substituents standing in adjacent position in the aryl nucleus; Me stands for Cu, Cr or Co; R 3 stands for --CH 3 or --COOH; R 3 ' stands for --OH or NH 2 ; R 4 stands for hydrogen, chlorine or methyl; R 4 ' stands for hydrogen, chlorine or methyl; R 5 stands for hydrogen, methoxy or acylamino wherein acyl stands for acetyl, hydroxy acetyl, sulfoacetyl, benzoyl, aminobenzoyl, methanesulfonylamino, or aminophenyl sulfonylamido; R 6 stands for hydrogen, hydroxyl or nitro; R 7 stands for hydrogen, chlorine or nitro; R 8 stands for NH 2 or acylamino, wherein acyl is as defined above; R 9 stands for NH 2 or alkyl amino having 1-4 carbon atoms in the alkyl group; R 10 stands for acylamino, where acyl is as defined above; q stands for the number 0 or 1; p stands for the number 0, 1 or 2; s stands for an integer ranging from 0 to 3; t stands for an integer ranging from 1 to 3; and k stands for the number 1 or 2, the dyestuff must contain at least one sulfo group.

Claim 4

A reactive dyestuff of claim 1 where R stands for hydrogen or methyl; R 1 stands for amino; lower alkyl amino; cyanoloweralkylamino, hydroxy lower alkyl amino, benzylamino, phenylamine, sulfophenylamino, chlorophenylamino, bromophenylamino, loweralkyl phenylamino, lower alkoxy phenylamino, carboxy phenylamino, N,N di lower alkylamino, N-lower alkyl-N-cyano lower alkylamino, N-lower alkyl-N-hydroxy lower alkylamino, N-lower alkyl-N-benzylamino, N-lower alkyl-N-phenylamino, N-lower alkyl-N-sulfophenylamino, N-lower alkyl-N-chlorophenylamino, N-lower alkyl N-bromophenyl amino, N-lower alkyl-N-lower alkoxy phenylamino, N lower alkyl-N-carboxy phenyl amino, N,N-dihydroxy lower alkylamino, N-hydroxy lower alkyl-N-cyano lower alkylamino, N-hydroxy lower alkyl-N-benzylamino, N-hydroxy lower alkyl-N-phenyl amino, N-hydroxy lower alkyl-N-sulfophenylamino, N-hydroxy lower alkyl-N-chlorophenylamino, N-hydroxy lower alkyl-N-bromophenylamino, N-hydroxy lower alkyl-N-lower alkyl phenyl amino, N-hydroxy lower alkyl N-lower alkoxy phenylamino, N-hydroxy lower alkyl-N-carboxy lower alkylamino, N,N-dicyanolower alkyl amino, N-cyano lower alkyl-N-benzylamino, N-cyano lower alkyl-N-phenylamino, N-cyano lower alkyl-N-sulfophenyl amino, N-cyanolower alkyl-N-chlorophenylamino, N-cyano lower alkyl-N-bromophenylamino, N-cyano lower alkyl-N-lower alkyl phenylamino, N-cyano lower alkyl-N-lower alkoxy phenylamino, N-cyano lower alkyl-N-carboxyphenylamino, N,N-dibenzylamino, N-benzyl-N-phenylamino, N-benzyl-N-sulfophenylamino, N-benzyl-N-chlorophenylamino, N-benzyl-N-bromophenylamino, N-benzyl-N-lower alkoxy phenylamino, N-benzyl-N-carboxy phenylamino, lower alkoxy, or lower alkoxy substituted lower alkoxy; and F is fluoro.

Claim 5

Dyestuff of claim 1 wherein D is a monovalent metal-free or metal-containing mono or polyazo dyestuff radical.

Claim 6

The dyestuff of claim 1 of the formula ##STR56##

Claim 7

The dyestuff of claim 1 of the formula ##STR57##

Claim 8

The dyestuff of claim 1 of the formula ##STR58##

Claim 9

The dyestuff of claim 1 of the formula ##STR59##

Claim 10

The dyestuff of claim 1 of the formula ##STR60##

Claim 11

The dyestuff of claim 1 of the formula ##STR61##

Claim 12

The dyestuff of claim 1 of the formula ##STR62##

Claim 13

The dyestuff of claim 1 of the formula ##STR63##

Claim 14

The dyestuff of claim 1 of the formula ##STR64##

Claim 15

The dyestuff of claim 1 of the formula ##STR65##

Claim 16

The dyestuff of claim 1 of the formula ##STR66##

Claim 17

The dyestuff of claim 1 of the formula ##STR67##

Claim 18

The dyestuff of claim 1 of the formula ##STR68##

Claim 19

The dyestuff of claim 1 of the formula ##STR69##

Claim 20

The dyestuff of claim 1 of the formula ##STR70##

Claim 21

The dyestuff of claim 1 of the formula ##STR71##

Claim 22

The dyestuff of claim 1 of the formula ##STR72##

Claim 23

The dyestuff of claim 1 of the formula ##STR73##

Claim 24

The dyestuff of claim 1 of the formula ##STR74##

Claim 25

A water-soluble reactive dyestuff of the formula ##STR75## wherein B is the radical of a carbocyclic diazo component of the benzene or naphthalene series; and E is the radical of a coupling component of the hydroxy benzene, hydroxy naphthalene, aminonaphthalene, 5-pyrazolone, or acetoacetic acid arylamide series said radicals bound with a ring carbon atom to the azo bridge or if E is of the acetoacetic acid arylamide series said radical is bound with an acyclic carbon atom to the azo bridge; B--N═N--E contains sulfonic acid groups; R stands for hydrogen, or lower alkyl; R 1 stands for NH 2 ; hydroxy; mercapto; methyl; trichloromethyl; phenyl; methylphenyl; chlorophenyl; sulfophenyl; hydroxyphenyl; morpholino; piperidino; hydrazino, N-methylhydrazino; lower alkyl amino; cyanoloweralkylamino, hydroxy lower alkyl amino, benzylamino, phenylamino, sulfophenyl amino, chlorophenylamino, bromophenylamino, lower alkylphenylamino, lower alkoxy phenylamino, carboxy phenylamino, N,N-dilower alkylamino, N-lower alkyl-N-cyano lower alkylamino, N-lower alkyl-N-hydroxy lower alkylamino, N-lower alkyl-N-benzylamino, N-lower alkyl-N-phenylamino, N-loweralkyl-N-sulfophenylamino, N-lower alkyl-N-chlorophenylamino, N-lower alkyl-N-bromophenyl amino, N-lower alkyl-N-lower alkylphenylamino, N-lower alkyl-N-lower alkoxyphenylamino, N-lower alkyl-N-carboxyphenylamino, N,N-dihydroxy lower alkylamino, N-hydroxy lower alkyl-N-cyano lower alkylamino; N-hydroxy lower alkyl-N-benzylamino, N-hydroxy lower alkyl-N-phenylamino, N-hydroxy lower alkyl-N-sulfophenylamino, N-hyroxy lower alkyl-N-chlorophenylamino, N-hydroxy lower alkyl-N-bromophenylamino, N-hydroxy lower alkyl-N-lower alkylphenylamino, N-hydroxy lower alkyl-N-lower alkoxyphenylamino, N-hydroxy lower alkyl-N-carboxy lower alkylamino, N,N-dicyano lower alkylamino, N-cyano lower alkyl-N-benzylamino, N-cyano lower alkyl-N-phenylamino, N-cyano lower alkyl-N-sulfophenylamino, N-cyano lower alkyl-N-chlorophenylamino, N-cyano lower alkyl-N-bromophenylamino, N-cyano lower alkyl-N-lower alkyl phenylamino, N-cyano lower alkyl-N-lower alkoxy phenylamino, N-cyano lower alkyl-N-carboxylphenylamino, N,N-dibenzylamino, N-benzyl-N-phenylamino, N-benzyl-N-sulfophenylamino, N-benzyl-N-chlorophenylamino, N-benzyl-N-bromophenylamino, N-benzyl-N-lower alkoxyphenylamino, N-benzyl-N-carboxyphenylamino, phenyloxy, sulfophenyloxy, lower alkoxy, lower alkoxy substituted lower alkoxy, lower alkylmercapto, hydroxy lower alkylmercapto, phenylmercapto, chlorophenylmercapto, or sulfophenylmercapto; and F is fluoro.

Claim 26

A water-soluble reactive dyestuff of the formula ##STR75## wherein B is the radical of a carbocyclic diazo component of the benzene or naphthalene series; and E is the radical of a coupling component of the hydroxy benzene, hydroxy naphthalene, aminonaphthalene, 5-pyrazolone, or acetoacetic acid arylamide series said radicals bound with a ring carbon atom to the azo bridge or if E is of the acetoacetic acid arylamide series said radical is bound with an acyclic carbon atom to the azo bridge; B--N═N--E contains sulfonic acid groups; R stands for hydrogen, or lower alkyl; R 1 stands for NH 2 ; hydroxy; mercapto; methyl; trichloromethyl; phenyl; methylphenyl; chlorophenyl; sulfophenyl; hydroxyphenyl; morpholino; piperidino; hydrazino, N-methylhydrazino; lower alkyl amino; cyanoloweralkylamino, hydroxy lower alkyl amino, benzylamino, phenylamino, sulfophenyl amino, chlorophenylamino, bromophenylamino, lower alkylphenylamino, lower alkoxy phenylamino, carboxy phenylamino, N,N-dilower alkylamino, N-lower alkyl-N-cyano lower alkylamino, N-lower alkyl-N-hydroxy lower alkylamino, N-lower alkyl-N-benzylamino, N-lower alkyl-N-phenylamino, N-loweralkyl-N-sulfophenylamino, N-lower alkyl-N-chlorophenylamino, N-lower alkyl-N-bromophenyl amino, N-lower alkyl-N-lower alkylphenylamino, N-lower alkyl-N-lower alkoxyphenylamino, N-lower alkyl-N-carboxyphenylamino, N,N-dihydroxy lower alkylamino, N-hydroxy lower alkyl-N-cyano lower alkylamino; N-hydroxy lower alkyl-N-benzylamino, N-hydroxy lower alkyl-N-phenylamino, N-hydroxy lower alkyl-N-sulfophenylamino, N-hyroxy lower alkyl-N-chlorophenylamino, N-hydroxy lower alkyl-N-bromophenylamino, N-hydroxy lower alkyl-N-lower alkylphenylamino, N-hydroxy lower alkyl-N-lower alkoxyphenylamino, N-hydroxy lower alkyl-N-carboxy lower alkylamino, N,N-dicyano lower alkylamino, N-cyano lower alkyl-N-benzylamino, N-cyano lower alkyl-N-phenylamino, N-cyano lower alkyl-N-sulfophenylamino, N-cyano lower alkyl-N-chlorophenylamino, N-cyano lower alkyl-N-bromophenylamino, N-cyano lower alkyl-N-lower alkyl phenylamino, N-cyano lower alkyl-N-lower alkoxy phenylamino, N-cyano lower alkyl-N-carboxylphenylamino, N,N-dibenzylamino, N-benzyl-N-phenylamino, N-benzyl-N-sulfophenylamino, N-benzyl-N-chlorophenylamino, N-benzyl-N-bromophenylamino, N-benzyl-N-lower alkoxyphenylamino, N-benzyl-N-carboxyphenylamino, phenyloxy, sulfophenyloxy, lower alkoxy, lower alkoxy substituted lower alkoxy, lower alkylmercapto, hydroxy lower alkylmercapto, phenylmercapto, chlorophenylmercapto, or sulfophenylmercapto; and F is fluoro.