Water-soluble disazo compound having arylcarboxamide diazo...

Details Water-soluble disazo compound having arylcarboxamide diazo... Water-soluble disazo compound having arylcarboxamide diazo...

2000-04-19

2001-08-28

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C008S549000

Reexamination Certificate

active

06281340

ABSTRACT:

DESCRIPTION
The present invention relates to the technical field of fiber-reactive disazo dyes. Various patent documents disclose disazo dyes which have fiber-reactive dye properties and dye for example cotton in dark blue to black shades. These include dyes which contain a diazo component having a carboxamide function formed from an aromatic carboxylic acid derivative and an aliphatic amine. Examples are DE-A 39 05 074, DE-A 39 05 270, EP-A 208 655, EP-A 221 013, EP-A 284 568, EP-A 309 406, EP-A 381 133 and EP-A 559 617. The application properties of these dyes, for example color strength and build-up behavior as a function of the dyeing process, are in need of improvement in some instances, however.
It has now been found that disazo class reactive dyes based on 1-amino-8-hydroxy-naphthalenedisulfonic acids which contain at least one diazo component having an N arylcarboxamide function formed from an aromatic carboxylic acid derivative and an aromatic amine have improved application properties.
The present invention thus provides reactive dyes of the general formula I
where
D
1
and D
2
each represent a group of the general formula II
where
R
1
is hydrogen, (C
1
-C
4
)-alkyl, aryl or substituted aryl; and
R
2
and R
3
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido or halogen;
A is a phenylene group of the general formula III
where
R
4
and R
5
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido or halogen;
a naphthylene group of the general formula IV
where
R
6
and R
7
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido or halogen;
or a polymethylene group of the general formula V
—(CR
8
R
9
)
k
—  (V)
 where
k is an integer greater than 1; and
R
8
and R
9
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, cyano, amido, halogen or aryl; and
X is hydrogen or —SO
2
—Z; or
represent a phenyl radical of the general formula VI
where
R
10
and R
11
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido or halogen; and
X
2
has one of the meanings of X
1
; or
represent a naphthyl radical of the general formula VII
where
R
12
and R
13
are independently hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido or halogen;
X
3
has one of the meanings of X
1
;
Z is —CH═CH
2
, —CH
2
CH
2
Z
1
or hydroxyl,
where
Z
1
is hydroxyl or an alkali-detachable group; and
M is hydrogen or an alkali metal;
where at least one of D
1
and D
2
is a group of the general formula II;
where, if A is a group of the general formula V, R
1
is aryl or substituted aryl; and
where the reactive dye of the general formula I contains at least one —SO
2
—Z group.
The individual symbols in the general formulae can be identical to or different from each other within the scope of their definitions. (C
1
-C
4
)-Alkyl R may be straight-chain or branched and is in particular methyl, ethyl, n-propyl, isopropyol, n-butyl, isobutyl, sec-butyl or tert-butyl. Methyl and ethyl are preferred. The same logic applies to (C
1
-C
4
)-alkoxy groups. Aryl R is in particular phenyl. Substituted aryl R
1
is in particular phenyl substituted by one, two or three independent groups selected from the group consisting of (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxyl, sulfo, carboxyl, amido and halogen. Halogen R is in particular fluorine, chlorine or bromine, and chlorine and bromine are preferred.
Alkali-eliminable Z
1
in the &bgr;-position of the ethyl group of Z include for example halogen atoms, such as chlorine and bromine, ester groups of organic carboxylic and sulfonic acids, as of alkylcarboxylic acids, substituted or unsubstituted benzenecarboxylic acids and substituted or unsubstituted benzenesulfonic acids, such as alkanoyloxy of 2 to 5 carbon atoms, especially acetyloxy, benzoyloxy, sulfobenzoyloxy, phenylsulfonyloxy and toluylsulfonyloxy, also acidic ester groups of inorganic acids, as of phosphoric acid, sulfuric acid and thiosulfuric acid (phosphato, sulfato and thiosulfato groups), similarly dialkylamino groups having alkyl groups of 1 to 4 carbon atoms in each case, such as dimethylamino and diethylamino. Z is preferably vinyl, &bgr;-chloroethyl and particularly preferably &bgr;-sulfatoethyl.
The groups “sulfo”, “carboxyl”, “thiosulfato”, “phosphato” and “sulfato” include not only their acid form but also their salt form. Accordingly, sulfo groups are groups conforming to the general formula —SO
3
M, thiosulfato groups are groups conforming to the general formula —S—SO
3
M, carboxyl groups are groups conforming to the general formula —COOM, phosphato groups are groups conforming to the general formula —OPO
3
M
2
and sulfato groups are groups conforming to the general formula —OSO
3
M, in each of which M is as defined above.
The dyes of the general formula I may possess different fiber-reactive groups —SO
2
Z within the meaning of Z. More particularly, the fiber-reactive groups —SO
2
Z may be on the one hand vinylsulfonyl groups and on the other —CH
2
CH
2
Z
1
groups, preferably &bgr;-sulfatoethylsulfonyl groups. If the dyes of the general formula I contain vinylsulfonyl groups in some instances, then the fraction of the respective dye with the vinyisulfonyl group is up to about 30 mol %, based on the respective amount of total dye.
Alkali M is in particular lithium, sodium or potassium. M is preferably hydrogen or sodium.
k is preferably 2 or 3.
R
1
to R
13
are each preferably hydrogen and R
6
, R
7
, R
12
and R
13
are each preferably sulfo as well.
When A is phenylene and X
1
is —SO
2
Z, the SO
2
Z group is preferably disposed meta or para relative to the nitrogen atom. In the group of the general formula II, the carboxamide group is preferably disposed para or meta relative to the diazo group. When A is naphthylene, the bond leading to the nitrogen atom is preferably attached to the naphthalene nucleus in the &bgr;-position. When D
1
or D
2
is a group of the general formula VII, then the bond which leads to the diazo group is preferably attached to the naphthalene nucleus in the &bgr;-position.
When D
1
or D
2
is a group of the general formula VI and X
2
is —SO
2
Z, then the SO
2
Z group is preferably disposed meta or para relative to the diazo group.
Examples of substituents A are in particular 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2-chloro-1,4-phenylene, 2-chloro-1,5-phenylene, 2-bromo-1,4-phenylene, 2-sulfo-1,4-phenylene, 2-sulfo-1,5-phenylene, 2-methoxy-1,5-phenylene, 2-ethoxy-1,5-phenylene, 2,5-dimethoxy-1,4-phenylene, 2-methoxy-5-methyl-1,4-phenylene, 2-methyl-1,4-phenylene, 2,6-naphthylene, 2,8-naphthylene, 1-sulfo-2,6-naphthylene, 6-sulfo-2,8-naphthylene or 1,2-ethylene and 1,3-propylene. A is particularly preferably 1,3-phenylene, 1,4-phenylene, 2-sulfo-1,4-phenylene, 2-methoxy-1,5-phenylene, 2,5-dimethoxy-1,4-phenylene, 2-methoxy-5-methyl-1,4-phenylene or 1,2-ethylene and 1,3-propylene, and in the case of the two last-mentioned alkylene groups R
1
is preferably phenyl or 2-sulfophenyl.
Examples of groups D
1
and D
2
of the general formulae VI and VII are 2-(&bgr;-sulfatoethylsulfonyl)-phenyl, 3-(&bgr;-sulfatoethylsulfonyl)-phenyl, 4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-carboxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-chloro-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-chloro-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-bromo-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-sulfo-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-sulfo-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methoxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-ethoxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2,5-dimethoxy-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methoxy-5-methyl-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methyl-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2- or 3- or 4-(&bgr;-thiosulfatoethylsulfonyl)-phenyl, 2-methoxy-5-(&bgr;-thiosulfatoethylsulfonyl)-phenyl, 2-sulfo-4-(&bgr;-phosphatoethylsulfonyl)-phenyl, 2- or 3- or 4-vinylsulfonyl-phenyl, 2-sulfo-4-vinylsu

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