Naphtholsulphonic acid compounds, their preparation and use as coupling components

Claim 2

A naphtholsulphonic acid substituted with an ammonium group and, in the betaine form, corresponding to the formula wherein X is --CO-- or --SO 2 --, R 1 is hydrogen or alkyl, R 2 and R 3 each independently is alkyl, alkenyl or phenylalkyl, R 4 is alkyl, alkenyl, phenylalkyl or ##STR31## Y is alkylene or xylylene, m is 1 or 2, n is 0 or 1, R 5 and R 6 each independently is hydrogen, alkyl, alkoxy or halogen, and in addition, if n=1, R 2 or R 4 may be amino, alkylamino, dialkylamino, cycloalkyl, phenyl, or phenyl substituted by halogen, C 1-4 -alkyl, C 1-4 -alkoxy or cyano, R 2 and R 3 , together with the nitrogen atom to which they are bonded may form optionally C 1 -C 4 -alkyl-substituted pyrrolidine, piperidine, morpholine, piperazine or N-hydroxyethyl-piperazine, R 2 , R 3 and R 4 , together with the nitrogen atom to which they are bonded may form a pyridinium ring, or a group of the formula ##STR32## R 2 , R 3 and R 4 may be hydrogen, Y is phenylene, which is optionally substituted by hydroxyl, halogen, cyano, C 1-4 -alkyl or C 1 -C 4 -alkoxy, benzylene or a radical of the formula ##STR33## Z is a direct bond, --(CH 2 ) p --, --O--, --O--(CH 2 ) p --O, --SO 2 --, --NHCO--, --NHCONH--, --NHCO--(CH 2 ) p --CONH-- or --CONH--(CH 2 ) p --NHCO--, p is 1, 2 or 3, and R 7 is hydrogen, alkyl, alkoxy or halogen.

Claim 3

A substituted naphtholsulphonic acid which, in the betaine form is of the formula ##STR34## wherein X is --CO-- or --SO 2 --, R 1 ' is hydrogen or C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, R 2 ', R 3 ' and R 4 ', each independently is C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, or benzyl or phenylethyl which is optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or R 4 ' may be ##STR35## Y' is C 1 -C 8 -alkylene which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, or xylylene which is optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, m is 1 or 2, n is 0 or 1, and R 5 ' and R 6 ', each independently is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, and in addition, if n=1, R 2 ' or R 4 ' may be amino, C 1 -C 4 -alkylamino or C 1 -C 4 -dialkylamino which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, phenyl which is optionally substituted by hydroxyl, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or optionally C 1 -C 4 -alkyl-substituted cyclopentyl or cyclohexyl, or R 2 ' and R 3 ', together with the N atom to which they are bonded form optionally C 1 -C 4 -alkyl-substituted pyrrolidine, piperidine, morpholine, piperazine or N-hydroxyethylpiperazine, or R 2 ', R 3 ' and R 4 ', together with the N atom to which they are bonded form a pyridinium ring, or a group of the formula ##STR36## or R 2 ', R 3 ' and R 4 ' may be hydrogen, and Y' is phenylene which is optionally substituted by hydroxyl, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, benzylene or a radical of the formula ##STR37## R 7 ' denotes hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, and Z is a direct bond, --(CH 2 ) p --, --O--, --O--(CH 2 ) p --O, --SO 2 --, --NHCO--, --NHCONH--, --NHCO--(CH 2 ) p --CONH-- or --CONH--(CH 2 ) p --NHCO-- and p is 1, 2 or 3.

Claim 4

A substituted naphtholsulphonic acid which, in the betaine form is of the formula ##STR34## wherein X is --CO-- or --SO 2 --, R 1 ' is hydrogen or C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, R 2 ', R 3 ' and R 4 ', each independently is C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, or benzyl or phenylethyl which is optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or R 4 ' may be ##STR35## Y' is C 1 -C 8 -alkylene which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, or xylylene which is optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, m is 1 or 2, n is 0 or 1, and R 5 ' and R 6 ', each independently is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, and in addition, if n=1, R 2 ' or R 4 ' may be amino, C 1 -C 4 -alkylamino or C 1 -C 4 -dialkylamino which is optionally substituted by hydroxyl, halogen, cyano or C 1 -C 4 -alkoxy, phenyl which is optionally substituted by hydroxyl, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or optionally C 1 -C 4 -alkyl-substituted cyclopentyl or cyclohexyl, or R 2 ' and R 3 ', together with the N atom to which they are bonded form optionally C 1 -C 4 -alkyl-substituted pyrrolidine, piperidine, morpholine, piperazine or N-hydroxyethylpiperazine, or R 2 ', R 3 ' and R 4 ', together with the N atom to which they are bonded form a pyridinium ring, or a group of the formula ##STR36## or R 2 ', R 3 ' and R 4 ' may be hydrogen, and Y' is phenylene which is optionally substituted by hydroxyl, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, benzylene or a radical of the formula ##STR37## R 7 ' denotes hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, and Z is a direct bond, --(CH 2 ) p --, --O--, --O--(CH 2 ) p --O, --SO 2 --, --NHCO--, --NHCONH--, --NHCO--(CH 2 ) p --CONH-- or --CONH--(CH 2 ) p --NHCO-- and p is 1, 2 or 3.

Claim 5

A substituted naphtholsulphonic acid according to claim 2, wherein: m is 1, R 1 ' is hydrogen or methyl, R 2 ', R 3 ' and R 4 ', each independently is C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, chlorine, bromine, cyano or C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, or benzyl or phenylethyl which is optionally substituted by chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or R 4 ' may be ##STR38## Y' is C 1 -C 4 -alkylene which is optionally substituted by hydroxyl, chlorine, bromine, cyano or C 1 -C 4 -alkoxy, or xylylene which is optionally substituted by chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and R 5 ' and R 6 ', each independently is hydrogen, methyl, methoxy, ethoxy or chlorine, and in addition, if n=1, R 2 ' or R 4 ' is amino, phenyl which is optionally substituted by hydroxyl, chlorine, bromine, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or optionally C 1 -C 4 -alkyl-substituted cyclopentyl or cyclohexyl, or R 2 ' and R 3 ', together with the N atom to which they are bonded form pyrrolidine, piperidine, morpholine, piperazine, N-methyl-piperazine or N-hydroxyethylpiperazine, or R 2 ', R 3 ' and R 4 ', together with the N atom to which they are bonded form a pyridinium ring, or R 2 ', R 3 ' and R 4 ' are hydrogen.

Claim 6

Naphtholsulphonic acid compounds which, in the betaine form, correspond to the general formula ##STR39## wherein R 1 " denotes hydrogen or methyl, R 2 "', R 3 "' and R 4 "', independently of one another, denote C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, chlorine, bromine, cyano or C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, or benzyl or phenylethyl which is optionally substituted by chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and R 5 "' and R 6 "', independently of one another, denote hydrogen, methyl, methoxy, ethoxy, chlorine or bromine.

Claim 7

Naphtholsulphonic acid compounds which, in the betaine form, correspond to the general formula ##STR39## wherein R 1 " denotes hydrogen or methyl, R 2 "', R 3 "' and R 4 "', independently of one another, denote C 1 -C 4 -alkyl which is optionally substituted by hydroxyl, chlorine, bromine, cyano or C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, or benzyl or phenylethyl which is optionally substituted by chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, and R 5 "' and R 6 "', independently of one another, denote hydrogen, methyl, methoxy, ethoxy, chlorine or bromine.