Reactive dyes containing a linkage

Details Reactive dyes containing a linkage Reactive dyes containing a linkage

2001-01-31

2002-03-19

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S605000, C534S612000, C008S549000

Reexamination Certificate

active

06359121

ABSTRACT:

This invention relates to reactive dyes having a bridging group between triazinylamino groups each attached to a chromophore.
GB-A-1283771 and EP-A-0625551 disclose respective general ranges of reactive dyes of the formula (A)
where D is a chromophore (which in the case of GB-A-1283771 is specifically a naphthylazo-phenylene or -naphthalene containing at least 3 sulphonic acid groups and in the case of EP-A-0625551 is any of a wide range of chromophores), R is H or an optionally substituted C
1-4
alkyl group and X specifically a linking group which, in the case of GB-A-1283771, is an aromatic group selected from phenylene, diphenylene and naphthalene nuclei, and in the case of EP-A-0625551 is an aliphatic linking group, the group —NHXNH— forming a bridging group between receptive triazine nuclei. The dyes of GB-A-1283771 offer a degree of fixation over a wide range of liquor to goods ratios and provide shades of very good light fastness, while those of EP-A-0625551 show good fastness and build up properties.
JP-A-62-172062 discloses a wide range of dyestuffs in which chromophores are linked by the specific group
wherein Y is hydrogen, halogen or alkyl and Z is the reactive group —CH═CH
2
or —CH
2
CH
2
OSO
3
H.
One of many examples of dyes disclosed has the following formula
In our WO-A-99/05224, we describe a range of dyes in which the bridging group is derived from an aminoalkyl piperazine, which dyes have the formula (B)
wherein:
each of R
1
, R
2
, R
3
and R
4
, independently, is H or an optionally substituted alkyl group;
each of X
1
and X
2
, independently, is a labile atom or group;
each of x and y, independently, is 0 or 1 and at least one of x and y is 1;
each of a and b, independently, is 2 to 5;
z is zero or is 1 to 4; and
when each of x and y is 1, a>b;
the or each R
5
, independently, is alkyl; and
each of D
1
and D
2
, independently, is a monoazo or polyazo chromophore, or a metallized derivative thereof.
We have found surprisingly that if, in dyes of the above formula (A), the chromophore D is a particular disazo dye, defined below, then such dyes, especially when used for exhaust dyeing of cellulosic materials, can exhibit excellent all-round fastness properties and build-up and compatibility with other dyes whose preferred exhaust temperature is 80° C. or, more preferably, above.
Thus, according to one aspect, the invention provides a dye of the formula (I)
D
1
—Y—D
2
  (I)
wherein each of D
1
and D
2
independently is a chromophore of the formula
in which
X is fluorine, chlorine or optionally substituted pyridinium;
an SO
3
H is present in the 5- or 6-position (preferably the 6-position) of the naphthalene nucleus;
n is zero or 1 (preferably 1); and
in which
Z is a C
5-12
aliphatic or aromatic cyclic hydrocarbon group, optionally additionally containing at least one hetero atom selected from N, O and S and optionally substituted by at least one of C
1-4
alkyl and SO
3
H (or a salt thereof); or
at least two said cyclic hydrocarbon groups linked together; or
a C
1-15
alkylene or C
2-15
alkenylene chain, which said chain
(a) optionally additionally contains, so as to be interrupted or terminated by, at least one of (1) at least one hetero atom selected from N, O and S and (2) at least one C
5-12
aliphatic or aromatic cyclic hydrocarbon group, which said cyclic hydrocarbon group optionally additionally contains at least one hetero atom selected from N, O and S and is optionally substituted by at least one of C
1-4
alkyl and SO
3
H (or a salt thereof); and
(b) is optionally substituted by C
1-4
alkyl, hydroxy-C
1-4
alkyl, amino-C
1-4
alkyl, hydroxyl, carboxyl or amino, which amino group or moiety is optionally substituted by one or two C
1-4
alkyl groups, or by a substituent group which, together with (i) one of R
1
, R
2
and R
3
(each defined below), (ii) the nitrogen atom to which R
1
, R
2
or R
3
is attached and (iii) a chain length of Z between the said nitrogen and the substituent group, forms a heterocyclic group; and
each of R
1
, R
2
and R
3
, independently, is hydrogen, a C
1-4
alkyl, hydroxy-C
1-4
alkyl or amino-C
1-4
alkyl group or each of R
1
and R
2
, together with the respective nitrogen atoms to which they are attached and the chain Z therebetween, forms a heterocyclic group or (as defined above) one of R
1
, R
2
and R
3
, together with (i) the nitrogen atom to which it is attached, (ii) the said substituent group on the chain Z and (iii) the said chain length between the said nitrogen atom and the said substituent group, forms a heterocyclic group; and
Y is other than
 (and preferably contains no reactive group); or a sulphonic acid salt of the said dye of the formula (I).
When X is a substituted pyridinium, preferred substituents are 3-carboxyl, 3-carbonamido and 4-carboxyl.
In one preferred range of dyes, Z is a C
1-10
alkylene chain optionally substituted by at least one group selected from C
1-4
alkyl, hydroxy and carboxyl. Such chains may be free from any hetero atom or may contain additionally at least one hetero atom selected from O and N. More preferably, the chain is a C
2-8
-alkylene chain which is unsubstituted or substituted by at least one group selected from methyl, hydroxy and carboxyl. Still more preferably the chain is of the formula
[CH
2
]
x
wherein x is 2 or 3, which alkylene chain is unsubstituted or substituted by one or two methyl groups or a hydroxy or carboxyl group and each of R
1
, R
2
and R
3
independently is selected from hydrogen, C
1-4
alkyl and hydroxyethyl.
Examples of the group Y in which Z is a C
1-10
alkylene chain optionally substituted by at least one of C
1-4
alkyl, hydroxy and carboxyl are HNC
2
H
4
NH; HNC
3
H
6
NH; HNC
4
H
8
NH; HNC
5
H
10
NH; HNC
6
H
12
NH; HNC
8
H
16
NH; HNC
2
H
4
N(CH
3
); HNC
3
H
6
N(CH
3
); HNC
2
H
4
N(C
2
H
4
OH); HNC
2
H
4
N(C
3
H
6
OH); HNC
3
H
6
N(C
2
H
4
OH); HNC
2
H
4
N(C
2
H
5
); HNC
2
H
4
N(n-C
3
H
7
); HNC
3
H
6
N(C
2
H
5
); HNC
3
H
6
N(n-C
3
H
7
); (H
3
C)NC
2
H
4
N(CH
3
); (H
3
C)NC
3
H
6
N(CH
3
); (H
3
C)NC
2
H
4
N(C
2
H
5
); HNC
2
H
4
NH[CH(CH
3
)
2
]; (H
5
C
2
)NC
2
H
4
N(C
2
H
5
); HNC
2
H
4
NH[CH(CH
3
) (C
2
H
5
)]; HNC
2
H
4
N(n-C
4
H
9
); HNC
2
H
4
N[CH
2
CH(CH
3
) (OH)]; HNCH(CH
3
)CH
2
NH; HNC(CH
3
)
2
CH
2
NH; HNCH
2
CH(OH)CH
2
NH; HNCH
2
C(CH
3
)
2
CH
2
NH; HNCH(C
2
H
5
)CH
2
NH; HNCH
2
CH(CH
3
)C
3
H
6
NH; HNCH
2
CH(CH
3
)N [CH(CH
3
)
2
]; NHCH
2
C(CH
3
)
2
CH[CH(CH
3
)
2
]NH; HNC
2
H
4
S and HNCH(CO
2
H)CH
2
S.
Examples of the group Y in which Z is a C
1-10
alkylene chain additionally containing a hetero atom are HNC
3
H
6
N(CH
3
)C
3
H
6
NH; HNC
2
H
4
OC
2
H
4
OC
2
H
4
NH; and HNC
2
H
4
OC
2
H
4
NH.
The C
1-10
alkylene chain of Z may additionally contain an aliphatic or aromatic ring structure and examples of the group Y in which Z is such a chain are:
where n is 2 or 3, which is an example of the group Y in which Z is C
1-10
alkylene chain interrupted by an aliphatic ring containing at least one hetero atom. Of these groups,
are especially preferred.
Especially preferred examples of the group Y in which Z is a C
1-10
alkylene chain are NHC
2
H
4
NH; NHC
3
H
6
NH; NHCH(CH
3
)CH
2
NH; NHC
2
H
4
N(CH
3
); NHC
3
H
6
N(CH
3
); NHCH
2
CH(OH)CH
2
NH; NHC
2
H
4
N(C
2
H
4
OH); NHC(CH
3
)
2
CH
2
NH; NHC
3
H
6
N(C
2
H
4
OH); NHC
2
H
4
S; NHC
2
H
4
N(C
2
H
5), N(CH
3
)C
2
H
4
N(CH
3
); NHC
3
H
6
N(C
3
H
7
); N(C
2
H
4
OH)C
2
H
4
N(C
2
H
4
OH); HNCH(CO
2
H)CH
2
S; N[CH(CH
3
)
2
]CH(CH
3
)CH
2
NH; HNC
6
H
12
NH; HNC
3
H
6
N(CH
3
)C
3
H
6
NH; HNC
2
H
4
OC
2
H
4
NH; and HNC
2
H
4
OC
2
H
4
OC
2
H
4
NH.
In another preferred range of dyes, Z is a phenylene group, optionally substituted by a sulphonic acid group or one or more methyl group(s). Examples of the group Y in which Z is a phenylene group are:
or mixtures thereof, for example, a mixture of
In yet another preferred range of dyes Z is a C
1-15
alkylene chain and is substituted by a substituent group, preferably a C
1-10
alkylene group, which, together with (i) one of R
1
, R
2
and

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