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

2000-04-18

2001-04-10

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C008S549000

Reexamination Certificate

active

06214977

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to dark-blue bisazo compounds or salts thereof usable in dyeing or printing on fiber materials, particularly cellulose fiber materials, and their applications on fiber materials.
As reactive dyes of dark-blue color usable in dyeing or printing on cellulose fiber materials, dyes disclosed in JP-A-57-78458, JP-A-57-198757 and the like have been known.
The present inventors have conducted extensive researches for developing bisazocompounds or salts thereof capable of giving dyed products of dark-blue color which are superior in dyeing power, dyeing reproducibility, leveling property and dyeing performances such as 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, perspiration-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 and the one triazine ring being substituted with one vinylsulfone fiber-reactive group through a divalent connecting group. The present invention thus have been completed.
SUMMARY OF THE INVENTION
The present invention provides a bisazo compound represented by the following general formula (1):
wherein R
1
and R
2
, which are the same to or different from each other, represent hydrogen or alkyl which may be optionally substituted, U represents a group selected from the groups represented by the following formulae (2a), (2b) or (2c):
wherein R
3
represents hydrogen or alkyl which may be optionally substituted, R
4
and R
5
represent hydrogen, alkyl which may be optionally substituted or phenyl, A
1
represents phenylene which may be optionally substituted or naphthylene which may be optionally substi tuted, A
2
represents alkylene which may be optionally substituted, Q
1
represents —O—, —S— or —NR
6
— wherein R
6
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
7
—(CH
2
)
m
—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
7
represents hydrogen or alkyl having 1 to 4 carbon atoms, and
m is an integer of 1 to 6,
X
1
and X
2
, which are the same to or different from each other, represent a group selected from fluoro, chloro, pyridinio which may be optionally substituted,
T represents a non-fiber reactive group represented by the following formulae (4a), (4b) or (4c):
 wherein R
8
represents hydrogen or alkyl which may be optionally substituted, R
9
represents alkyl which may be optionally substituted, cyano or phenyl which may be optionally substituted by one or two substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, carboxy, halogeno, hydroxyl, cyano, carbamoyl, carboxylic ester, amino, acylamino and alkylamino having 1 to 4 carbon atoms, R
10
represent hydrogen, alkyl which may be optionally substituted or phenyl which may be optionally substituted, Q
2
represents —CH
2
—, —O—, —S—, —SO
2
— or —NR
11
— wherein R
11
represents hydrogen or alkyl which may be optionally substituted, and n is 1, 2 or 3, and one of the two bonds marked with a symbol * means a bond connected to —U and the other means a bond connected to —T;
, and a salt thereof.
The present invention also provides a method for dyeing or printing a fiber material using the bisazo compound represented by the formula (1) 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.
In the formula (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, hydroxyalkoxy 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-(2-hydroxyethoxy)ethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, 1-hydroxymethyl-1-bmethylethyl, 1,1-di(hydroxymethyl)ethyl, 1,1-di(hydroxymethyl)-2-hydroxyethyl, 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.
U in the formula (1) represents a group selected from the groups represented by the formulae (2a), (2b) or (2c), described above. R
3
in the formula (2a) represents hydrogen or alkyl which may be optionally substituted. R
4
in the formula (2b) and R
5
in the formula (2c) represent hydrogen, alkyl which may be optionally substituted, or phenyl.
Examples of said alkyl represented by R
3
, R
4
or R
5
include alkyl same to those listed above as examples of R
1
and R
2
R
3
, R
4
and R
5
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 unsubstituted phenylene and phenylene 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 symbol # mean bonds connected to the group of —NR
3
—.
Particularly preferred examples of the phenylene include unsubstituted phenylene and phenylene substituted with one or two groups selected from methyl and methoxy.
Examples of the naphthylene represented by A
1
in the formula (2a) include naphthylene which may be bptionally substituted with one or two substituents selected from alkyl having 1 to 4 carbon atoms, alko

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