Reactive dyes containing a halobenzene nucleus

Details Reactive dyes containing a halobenzene nucleus Reactive dyes containing a halobenzene nucleus

2000-07-24

2002-06-04

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S618000, C534S634000, C534S635000, C534S636000, C534S637000, C534S638000, C534S642000, C540S126000, C540S134000, C544S076000, C544S189000

Reexamination Certificate

active

06399751

ABSTRACT:

This invention relates to reactive dyes containing a halobenzene nucleus and, in particular, reactive dyes of this type containing two or more reactive components.
Dyes are known which contain a halobenzene nucleus linked via an azo group to another aromatic nucleus such that the halobenzene nucleus forms part of the chromophoric chain (see for example GB-A-882001). Dyes of this type which contain two such halobenzene nuclei are disclosed in CA64,14316d (1966), which is an English language abstract of an article by Matsui et al, Yuki Gosei Kagaku Kyokai Shi (1966), 24(2), 132-136.
Dyes are also known in which the halobenzene nucleus is attached to a chromophoric group by a sulphonamide or amide linkage; see, for example, GB-A-978162 and CA59,12949g (1963), which is an English language abstract of an article by Matsui et al in Yuki Gosei Kagaku Kyokai Shi (1962), 20,1100-1112. Again dyes of this type may contain two such halobenzene nuclei; see GB-A-978162.
In other known dyes the halobenzene nucleus is linked to a chromophoric group by an amine linkage; see U.S. Pat. No. 3,301,847 and CA61,16193f (1964) which is an English language abstract of an article by Matsui et al in Kogyo Kagaku Zasshi, (1964), 67(1),94-97. However, such dyes contain only one reactive group.
We have now found surprisingly that dyes having at least one halobenzene nucleus linked to a chromophoric group via an amino linkage and additionally containing a second reactive group have particularly high build up, especially in warm dyeing applications.
According to the invention there is provided a dye containing
at least one chromophore D;
at least a first, halobenzene, reactive group Z
1
, of the formula (I)
in which:
n is 1 or 2
X, or each X independently, is an electron withdrawing group; and
Y is a halogen atom;
at least a second reactive group Z
2
selected from
(1) a group of the formula (I), given and defined above, but selected independently thereof;
(2) a group of the formula (II)
wherein
m is 1 or 2; p is 0 or 1; when m is 1, p is 1; and when m is 2, p is 0;
Y
1
, or each Y
1
independently, is a halogen atom or an optionally substituted pyridinium group; and
T is C
1-4
alkoxy, C
1-4
thioalkoxy or N(R
1
)(R
2
), in which each of R
1
and R
2
independently is hydrogen, optionally substituted C
1-4
alkyl or optionally substituted aryl;
(3) a group of the formula (III)
wherein:
x is 1, 2 or 3; y is zero, 1 or 2; and
x+y≦3;
Y
2
, or each Y
2
independently, is a halogen atom or an optionally substituted pyridinium group; and
U or each U independently, is C
1-4
alkyl or C
1-4
alkylsulphonyl;
(4) a group of the formula (IV)
—SO
2
CH
2
CH
2
X
1
  (IV)
wherein X
1
is an eliminatable group;
(5) a group of the formula (V)
—SO
2
(CH
2
)
z
CH═CH
2
  (V)
wherein z is zero or 1; and
(6) a group of formula (VI)
—W—C(R
10
)═CH
2
  (VI)
wherein:
R
10
is hydrogen, C
1-4
alkyl or halogen; and
W is —OC(═O)— or —N(R
11
)C(═O)— in which R
11
is hydrogen or C
1-4
alkyl;
at least a first linking group L
1
, linking the said first, halobenzene, reactive group Z
1
to one of components (i) the or a chromophore D and (ii) the second reactive group Z
2
, which said first linking group L
1
presents an amino nitrogen to the reactive group Z
1
and to the component (i) or (ii) or, when component (i) contains a heterocyclic nitrogen atom, is linked directly to the nitrogen atom and which said first linking group L
1
optionally includes a hydrocarbon bridging group, which hydrocarbon bridging group B has at least two carbon atoms, is optionally substituted, optionally includes at least one hetero atom and is optionally a chromophore; and
when Z
2
is selected from the said groups (I)-(III), at least a second linking group L
2
linking the second reactive group Z
2
to one of (i) the or a chromophore D and (ii) the said first reactive group Z
1
, which said linking group L
2
is selected from
(1) a linking group L
1
, but selected independently thereof; or
(2) an amide linkage; and
(3) a sulphonamide linkage; and
optionally at least one aromatic group Ar which, when Z
2
is selected from the said groups (IV)-(VI), may carry the said reactive group Z
2
.
Preferably, the linking group L
1
has the formula (VII)
1
N(R)  (VII)
1
wherein R is hydrogen or optionally substituted C
1-4
alkyl, such that the same amino group presents itself to each of the reactive group Z
1
and the component (i) or (ii), as defined above; or
is a piperazinoalkylamino group of the formula (VII)
2
wherein each R, independently, is as defined above, such that respective amino nitrogens, one of the piperazine group and the other of the alkylamino group, present themselves respectively, to the reactive group Z
1
and to the component (i) or (ii), as defined above; or
has the formula (VII)
3
—N(R)BN(R)—  (VII)
3
wherein B is a hydrocarbon bridging group as defined above, each R, independently, is as defined above and B is optionally linked additionally to at least one additional group —N(R).
The hydrocarbon bridging group B may be a straight or branched, optionally substituted, C
2-6
alkylene group optionally interrupted by at least one hetero atom, for example, O, S or N. Optional substituents are OH alkoxy, carboxy, carboxylic ester or carboxamide. Alternatively the bonding group B may be an optionally substituted arylene especially phenylene group. Optional substituents are SO
3
H and salts thereof, C
1-4
alkyl, C
1-4
alkoxy and chloro. The bridging group B is especially preferably an optionally substituted aryl group.
An especially preferred dye embodying the invention has the formula (VIII)
Z
1
—L
1
—D—(L
2
)
a
—Z
2
  (VIII)
wherein:
D is a chromophore;
each of L
1
and L
2
is an amine or piperazine linkage of the formula
—N(R)— (VII)
1
;
wherein:
R, or each R independently, is hydrogen or C
1-4
alkyl;
B is a hydrocarbon bridging group which has at least two carbon atoms, is optionally substituted, optionally includes at least one hetero atom and is optionally a chromophore;
a is zero or 1; and
b is from 2 to 6 inclusive;
Z
1
is a group
in which:
n is 1 or 2;
X, or each X independently, is an electron withdrawing group; and
Y is a halogen atom; and
when a is 1, Z
2
is:
a group of the formula (I), given and defined above but selected independently thereof; or
a group of the formula (II)
wherein:
m is 1 or 2; p is 0 or 1; when m is 1, p is 1; and when m is 2, p is 0;
Y
1
, or each Y
1
independently, is a halogen atom or an optionally substituted pyridinium group; and
T is C
1-4
alkoxy, thioalkoxy or N(R
1
)(R
2
) in which R
1
is hydrogen, optionally substituted C
1-4
alkyl or optionally substituted aryl and
R
2
is hydrogen or optionally substituted C
1-4
alkyl; or
a group of the formula (III)
wherein:
x is 1, 2 or 3; y is zero, 1 or 2; and x+y≦3;
Y
2
, or each Y
2
independently, is a halogen atom; and
U, or each U independently, is C
1-4
alkyl or C
1-4
alkylsulphonyl; and
when a is zero, Z
2
is:
—SO
2
CH
2
CH
2
X
1
  (IV)
in which X
1
is an eliminatable group; or
—SO
2
(CH
2
)
z
CH—CH
2
  (V)
wherein
z is zero or 1; or
a group of formula (VI)
—W—C(R
10
)═CH
2
  (VI)
wherein:
R
10
is hydrogen, C
1-4
alkyl or halogen; and
W is —OC(═O)— or —N(R
11
)C(═O)— in which R
11
is hydrogen or C
1-4
alkyl.
In the halobenzene nucleus of the formula (I), X or each X independently, may be selected from nitro, cyano, alkylsulphonyl, dialkylaminosulphonyl and sulphonic acid groups and salts thereof. Preferably, X or each X independently, is selected from nitro and cyano.
The halogen atom in the halobenzene nucleus of formula (I) is preferably fluorine or chlorine.
The group R in the linking group L
1
of formulae (1)-(3) may be any of hydrogen, methyl, ethyl, n- or i-propyl or n-, s- or t-butyl, but is preferably hydrogen.
In the dye of formula (VII), each of Z
1
and Z
2
, independently, is preferably a group of the above mentioned formula (I). Moreover, it is even more preferred that each of Z
1
and Z
2

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