Reactive diamine-linked azo dyes

Details Reactive diamine-linked azo dyes Reactive diamine-linked azo dyes

2000-01-24

2001-01-30

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S612000

Reexamination Certificate

active

06180765

ABSTRACT:

This invention relates to reactive dyes containing two units each comprising a monoazo or disazo chromophore linked to a triazinylamino group, each of which units is linked by a diamine unit disposed between the triazine rings.
GB-A-1 283771 discloses a range of reactive diamine dyes of the formula (A)
where D is naphthylazo-phenylene or naphthalene containing at least 3 sulphonic acid groups, R is H or an optional substituted C
1-4
alkyl group and X is specifically a phenylene, diphenylene or naphthalene nucleus. They offer a degree of fixation over a wide range of liquor to goods ratios and provide shades of very good light fastness.
U.S. Pat. No. 5,149,789 discloses a range of dyestuffs some of which have two or three halotriazine rings interconnected by an aromatic diamine unit or two aromatic diamine units respectively. In one such dye (Example 53), the linking diamine unit carries a phenylazo group. The dye has the formula
However, in contrast to the range of dyes disclosed in GB-A-1283771 above, neither substitution on the respective halotriazinylamino groups is a chromophore as such. Accordingly such a dye does not have a particularly high dyeing strength.
We have found surprisingly that if, in a dyestuff of the formula (A), the linking diamine additionally carries an arylazo group, then excellent build up properties can be achieved, as well as excellent light fastness and aqueous solubility. Moreover the dyes still offer a degree of fixation over a wide range of liquor to goods ratios. These properties manifest themselves especially when the dyes are used to exhaust dye cotton.
Thus according to one aspect the invention provides a dye of the formula (I)
wherein:
Ar
1
is an optionally substituted arylene group;
Ar
2
is an optionally substituted aryl group;
each of D
1
and D
2
, independently, is a chromophoric group;
each of R
1
, R
2
, R
3
and R
4
, independently, is H or alkyl; and
each of X
1
and X
2
independently, is a labile atom or group.
Preferably, each of X
1
and X
2
, independently, is a halogen atom or a pyridinium salt (typically a 3- or 4-carboxy pyridinium salt derived respectively from nicotinic and isonicotinic acid), and is more preferably F or Cl. Still more preferably, each of X
1
and X
2
is Cl.
It is also preferred that each of R
1
, R
2
, R
3
and R
4
, independently, is H or C
1-4
alkyl, more preferably hydrogen, methyl, ethyl or n- or I-propyl.
In the formula (I), it is preferred that Ar
1
, be an optionally substituted phenylene, naphthalene or diphenylene group; and a still more preferred range of dyes has the formula (II)
wherein
Ar
1
, is a phenylene, naphthalene or diphenylene group;
each of A
11
and B
11
, independently, is optionally present and is a halogen atom, an alkoxy group, hydroxy group or a sulphonic acid group or a salt thereof; and
each of D
1
, D
2
, R
1
, R
2
, R
3
, R
4
, X
1
, X
2
and Ar
2
are as defined above.
An especially preferred range of dyes has the formula (III)
wherein each of D
1
, D
2
, R
1
, R
2
, R
3
, R
4
, X
1
, X
2
, A
11
, B
11
and Ar
2
are as defined above.
It is also preferred for Ar
2
, in the formula (I), to be an optionally substituted phenyl group, still more preferably a phenyl group substituted by a vinylsulphone or a precursor thereof. Preferred precursors are a &bgr;-sulphatoethylsulphone, a &bgr;-acyloxy- (more preferably C
2-5
acyloxy-) ethylsulphone or allylsulphone, especially a &bgr;-sulphatoethylsulphone.
Each of D
1
and D
2
, independently, may be an optionally metallized monoazo chromophore of the formula (IV)
A—N═N—E  (IV)
wherein
one of A and E is attached to the reactive triazinylamino group;
A is derived from a diazotizable amine; and
E is derived from a coupling component.
Preferably in the formula (IV),
A Is an optionally substituted aryl group and when A is attached to the triazinylamino group the attachment may be from the aryl group or from a substituent thereon; and
E is an optionally substituted aryl or heteroaryl group and when E is attached to the triazinylamino group the attachment may be from the aryl or heteroaryl group or from a substituent thereon, or E is an acetoacetamidoaryl group wherein the aryl moiety is optionally substituted and wherein the azo linkage in the formula (IV) is linked to the methylene group of the acetoacetamidoaryl group and when E is attached to the triazinylamino group the attachment may be from the aryl moiety or from a substituent thereon.
Still more preferably,
the group E is attached to the triazinylamino group in formula (I);
A is a phenyl or naphthyl group, optionally substituted by at least one of an alkyl, halo, cyano, hydroxy, aryloxy, alkylsulphonyl or arylsulphonyl group or a carboxylic or sulphonic acid group or salt thereof; and
E is as aryl or heteroaryl group selected from phenyl, naphthyl, pyrazolyl, pyrazolonyl, pyridyl, pyridonyl and pyrimidinyl groups or is an acetoacetamidoaryl group;
which said aryl or heteroaryl group or aryl moiety of the acetoacetamidoaryl group is optionally substituted by an alkyl, phenyl, naphthyl or amino- (which may bear a C
1-4
alkyl group), amido- or sulphonamido-phenyl or naphthyl group and E may be attached to the triazinylamino group from the said substituted alkyl group, phenyl or naphthyl group or phenyl or naphthyl moiety of the said substituent;
which said aryl or heteroaryl group is further optionally substituted at least so as to provide the coupling component from which the group E is derived, with sufficient electron donating capacity to allow the coupling;
which said aryl moiety of the acetoacetamidoaryl group is optionally substituted, preferably by at least one of alkyl, alkoxy, halo, H
2
NCONH, CH
3
CONH or SO
3
H (or a salt thereof), more preferred alkyl and alkoxy being C
1-4
alkyl and C
1-4
alkoxy; and
when A is an &agr;-naphthol, which dye is optionally metallized.
The group E may be a pyrazolyl, pyrazolonyl, pyridyl, pyridonyl or pyrimidinyl group and is substituted by a hydroxyl, mercapto or amino group, which amino group is optionally substituted by at least one alkyl group.
However, more preferably, the group E is a phenyl or naphthyl group optionally substituted by an alkyl, alkoxy, ureido, acylamino, alkylsulphonyl, halo, hydroxyl or amino group, which amino group is optionally substituted by at least one alkyl group, or is a carboxylic or sulphonic acid group or a salt thereof. In these groups, the alkyl groups or moiety is preferably a C
1-4
alkyl group.
In a still more preferred range of dyes, in at least one of D
1
and D
2
, E is an optionally substituted phenylene group such as to provide, in the dye, at least one chromophore of the formula (V)
wherein:
A
1
is a phenyl or naphthyl group, optionally substituted by at least one of an alkyl, halo, cyano, hydroxy, aryloxy, alkylsulphonyl or arylsulphonyl group or a carboxylic or sulphonic acid group or salt thereof;
the or each R
6
, independently, is alkyl (preferably C
1-4
alkyl), alkoxy (preferably C
1-4
alkoxy), halo, H
2
NCONH, H
3
CCONH or SO
3
H (or a salt thereof); and
p is zero or is 1-4, preferably zero or 1-3, more preferably 1 or2.
For the avoidance of doubt it is confirmed that, in the above formula (V) and in subsequent formulae the unsubstituted bond {circle around (1)} indicates a link to a triazinylamino in the formula (I)
In one especially preferred range of dyestuffs, at least one of D
1
- and D
2
- has the formula (VI)
wherein:
A
1
is as defined above;
R
7
is alkyl (preferably C
1-4
alkyl),alkoxy (preferably C
1-4
alkoxy), halo, H
2
NCONH or H
3
CCONH; and R
8
is H, alkyl (preferably C
1-4
alkyl),alkoxy (preferably C
1-4
alkoxy) or halo.
Such chromophores tend to be yellow in colour.
Most preferably R
7
is H
2
NCONH and R
8
is hydrogen or R
7
is CH
3
CONH and R
8
is CH
3
O.
In the above dyes A
1
is especially preferably a phenyl or naphthyl group substituted by at least one SO
3
H group, or a salt thereof.
In another preferred range of monoazo dyes, at least one and more preferably each of D
1
and D
2
, independently, is a monoazo chromophore of

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