Bisazo compounds and process for dyeing or printing using them

Details Bisazo compounds and process for dyeing or printing using them Bisazo compounds and process for dyeing or printing using them

2000-03-24

2001-04-24

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S612000, C534S635000, C534S637000

Reexamination Certificate

active

06222023

ABSTRACT:

BACKGROUND OF THE INVENTION
The present Invention relates to dark-blue bisazo compounds usable in dyeing or printing on fiber materials, particularly cellulose fiber materials.
As reactive dyes of dark-blue color usable in dyeing or printing on fiber materials, dyes disclosedin JP-A-57-78458, JP-A-57-198757 and the like have been known.
The present inventors have conducted extensive researches for developing reactive dyes capable of giving dyed products of dark-blue color which are superior in dyeing power, dyeing reproducibility and dyeing performances such as leveling property, build-up property, effective dyeing rate and washing-off property compared with the known dark-blue dyes described above, and which are excellent in various fastness such as chlorine fastness, light fastness, perspiration fastness, perapiration-sunlight fastness, acid-hydrolysis fastness, alkali fastness, washing fastness and peroxide washing fastness. As the result, they have found that the aim can be attained with specific diazo compounds or salts thereof having two triazine rings on the terminal of their molecular structure, one triazine ring being substituted with two chloro and the other triazine ring being substituted with at least one vinylsulfone fiber-reactive group. The present invention thus have been completed.
SUMMARY OF THE INVENTION
The present invention provide a bisazo compound represented by the following general formula (1):
wherein one of X
1
and X
2
is hydroxyl and the other is amino, R
1
and R
2
which are the same to or different from each other, represent hydrogen or alkyl which may be optionally substituted, R
3
and R
4
, which are the same to or different from each other, represent hydrogen, sulfo, methyl, methoxy or chloro, m and n, which are the same to or different from each other, represent 0 or 1, U represents a group selected from the groups represented by the following formulae (2a), (2b) or (2c):
wherein R
5
represents hydrogen or alkyl which may be optionally substituted, R
6
and R
7
represent hydrogen, alkyl which may be optionally substituted or phenyl which may be optionally substituted, A
1
represents phenylene which may be optionally substituted or naphthylene which may be optionally substituted, A
2
represents alxylene which may be optionally substituted, Q
1
represents —O—, —S— or —NR
8
— wherein R
8
represents hydrogen, alkyl which may be optionally substituted or phenyl which may be optionally substituted, r and s, which are the same to or different from each other, represent 2, 3 or 4, Z
1
, Z
2
and Z
3
represent a fiber-reactive group selected from the groups represented by the following formulae (3a) or (3b):
—SO
2
—Y
1
  (3a)
—CONR
9
—(CH
2
)
p
—SO
2
—Y
2
,   (3b)
wherein Y
1
and Y
2
which are the same to or different from each other, represent —CH═CH
2
or —CH
2
CH
2
L wherein L is a group which can be eliminated by the action of an alkali, R
9
represents hydrogen or alkyl which may be optionally substituted, and p is an integer of 1 to 6, T represents a group selected from the groups represented by the formulae (2a), (2b) or (2c), fluoro, chloro, pyridinio which may be optionally substituted or a group selected from the groups represented by the following formulae (4a), (4b) or (4c):
wherein R
10
and R
11
, which are the same to or different from each other, represent hydrogen, alkyl which may be optionally substituted, cycloalkyl which may be optionally substituted or phenyl which may be optionally substituted, R
12
represent hydrogen, alkyl which may be optionally substituted, cycloalkyl which may be optionally substituted or phenyl which may be optionally substituted, Q
2
represents —CH
2
—, —O—, —S—, —SO
2
— or —NR
12
— wherein R
13
represents hydrogen or alkyl which may be optionally substituted, and q is 1, 2 or 3, or a salt thereof.
DETAILED DESCRIPTION OF THE INVENTION
The bisazo compound of the present invention is a compound represented by the general formula (1), shown above, wherein one of X
1
and X
2
represents hydroxyl and the other represents amino, and m and n, which are the same to or different from each other, represent 0 or 1. Preferably, at least one of m and n is 1.
R
1
and R
2
, which are the same to or different from each other, represent hydrogen or alkyl which may be optionally substituted. Said alkyl has preferably 1 to 4 carbon atoms. Examples of substituents on said alkyl include hydroxyl, cyano, alkoxy having 1 to 4 carbon atoms, halogeno, carbamoyl, carboxy, alkoxycarbonyl wherein the alkoxy has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl has 1 to 4 carbon atoms, sulfo and sulfamoyl.
The above alkyl, alkoxy as a substituent on said alkyl, alkoxycarbonyl wherein alkoxy has 1 to 4 carbon atoms and alkylcarbonyloxy wherein alkyl has 1 to 4 carbon atoms may be straight chain or branched chain.
Specific examples of alkyl which may be optionally substituted, represented by R
1
and R
2
, include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, 2,3-dihydroxypropyl, 3,4-dihydroxybutyl, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 2-hydroxy-3-methoxypropyl, chloromethyl, bromomethyl, 2-chloroethyl, 2-bromoethyl, 3-chloropropyl, 3-bromopropyl, 4-chlorobutyl, 4-bromobutyl, carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 1,2-dicarboxyethyl, carbamoylmethyl, 2-carbamoylethyl, 3-carbamoylpropyl, 4-carbamoylbutyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 4-ethoxycarbonylbutyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 2-methylcarbonyloxyethyl, 2-ethylcarbonyloxyethyl, 3-methylcarbonyloxypropyl, 3-ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl, 4-ethylcarbonyloxybutyl, sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, sulfamoylmethyl, 2-sulfamoylethyl, 3-sulfamoylpropyl and 4-sulfamoylbutyl.
R
1
and R
2
in the formula (I) are preferably hydrogen, methyl or ethyl, with hydrogen being particularly preferred.
R
3
and R
4
in the formula (I), which are the same to or different from each other, represent hydrogen, sulfo, methyl, methoxy or chloro, with hydrogen, sulfo, methyl and methoxy being preferred and hydrogen and sulfo being particularly preferred.
U in the formula (1) represents a group selected from the groups represented by the formulae (2a), (2b) or (2c), described above. R
5
in the formula (2a) represents hydrogen or alkyl which may be optionally substituted. Examples of said alkyl represented by R
5
has preferably 1 to 4 carbon atoms. Examples of substituents on said alkyl represented by R
5
include hydroxyl, cyano, alkoxy having 1 to 4 carbon atoms, halogeno, carbamoyl, carboxy, alkoxycarbonyl wherein the alkoxy has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl has 1 to 4 carbon atoms, sulfo and sulfamoyl.
R
6
in the formula (2b) and R
7
in the formula (2c) either have the same meaning as R
5
or they represent phenyl which may be optionally substituted.
R
5
is preferably hydrogen, methyl or ethyl,, and R
6
and R
7
are preferably hydrogen, methyl or ethyl.
In the formula (2a) described above, A
1
represents phenylene which may be optionally substituted or naphthylene which may be optionally substituted. Examples of the phenylene represented by A
1
include phenylene groups which may be optionally substituted with one or two substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo and halogeno, and the like.
Preferred examples of the phenylene represented by A
1
include phenylene which may be optionally substituted with one or two substituents selected from methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo.
Specific examples of the phenylene represented by A
1
include:
wherein bonds marked with a symbol # mean bonds connected to the gro

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