Reactive dyes, process for their preparation and their use

Details Reactive dyes, process for their preparation and their use Reactive dyes, process for their preparation and their use

2000-03-24

2002-09-17

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Reactive dye composition, process, or product

Alkylene sulfato, halotriazine, halodiazine,...

C008S918000, C008S687000, C008S688000, C534S635000, C534S637000, C534S642000

Reexamination Certificate

active

06451072

ABSTRACT:

The present invention relates to novel reactive dyes, to processes for their preparation and to their use for dyeing or printing fibre materials.
The practice of dyeing with reactive dyes has given rise in recent times to more stringent demands being made on the quality of the dyeings and on the economy of the dyeing process. For this reason, there is still a need for novel reactive dyes with improved properties, especially application properties.
Dyeing today calls for reactive dyes which have sufficient substantivity and which at the same time have good washing off properties with respect to unfixed dye. In addition, the dyes shall have a good tinctorial yield and high reactivity, and they shall also give, in particular, dyeings with high degrees of fixation. The dyes of the prior art do not meet these requirements in all respects.
This invention therefore has for its object to provide novel improved reactive dyes for dyeing and printing fibre materials and which have the above specified qualities to a high degree. The novel dyes shall be distinguished in particular by excellent fixation yields and superior fibre-dye bond stability, and further they shall have the property of being easily washed off to remove unfixed dye. They shall also produce dyeings with good allround fastness properties, for example lightfastness and wetfastness.
It has been found that this object is substantially achieved with the novel reactive dyes defined below.
This invention thus relates to reactive dyes of formula (1)
wherein
A is phenyl or naphthyl, each of which is unsubstituted or substituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxy, sulfo or a fibre-reactive group of formula (2a), (2b), (2c), (2d) or (2e)
—SO
2
—Y  (2a),
—NH—CO—(CH
2
)
1
—SO
2
—Y  (2b),
—CONH—(CH
2
)
m
—SO
2
—Y  (2c),
—NH—CO—CH(Hal)—CH
2
Hal  (2d)
or
—NH—CO—C(Hal)═CH
2
  (2e),
B is an aliphatic linking group,
D is the radical of a diazo component of the benzene or naphthalene series,
R
1
is hydrogen or unsubstituted or substituted C
1
-C
4
alkyl,
R
2
is hydrogen, cyano, carbamoyl or sulfomethyl,
R
3
is hydrogen or C
1
-C
4
alkyl,
R is hydrogen or unsubstituted or substituted C
1
-C
4
alkyl or corresponds to a radical of formula (3)
wherein B, D, R
2
and R
3
have the meanings cited above,
X
1
is halogen, hydroxy, C
1
-C
4
alkoxy, unsubstituted or substituted C
1
-C
4
alkylthio or amino, or a N-heterocycle which may contain additional heteroatoms,
Hal is chloro or bromo,
Y is vinyl or a —CH
2
—CH
2
—U radical, U is a group a which is removable with alkali, and l and m are each independently of the other the number 2, 3 or 4,
with the proviso that A and D are not simultaneously a phenyl radical which is substituted by the radical of formula (2a) if R is &bgr;-hydroxyethyl or &bgr;-sulfatoethyl and R
1
is C
1
-C
4
alkyl.
The novel dyes of formula (1) are fibre-reactive. Fibre-reactive compounds are to be understood as meaning compounds which are capable of reacting with the hydroxyl groups of the cellulose, amino, carboxy, hydroxy or thiol groups in wool and silk, or with the amino and, optionally, with the carboxy groups of synthetic polyamides with formation of covalent chemical bonds.
In the novel reactive dyes of formula (1) at least one of the radicals A and D contains a fibre-reactive group, or X
1
is halogen.
The dyes of formula (1) contain at least one, preferably 2 to 6 and, more preferably, 2 to 4, sulfo groups, which are either in the form of their free acid or, preferably, in the form of their salts. Suitable salts are, for example, the alkali metal salts, alkaline earth metal salts or ammonium salts, the salts of an organic amine, or mixtures thereof. Examples to be mentioned are the sodium, lithium, potassium or ammonium salts, the salt of mono-, di- or tri-ethanolamine, or Na/Li— or Na/Li/NH
4
mixed salts.
R and R
1
defined as unsubstituted or substituted C
1
-C
4
alkyl may be methyl, ethyl, n- or isopropyl or n-, sec-, tert- or isobutyl which is unsubstituted or substituted e.g. by hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C
1
-C
4
alkoxycarbonyl or carbamoyl, preferably by hydroxy, sulfo, sulfato or carboxy.
R is preferably hydrogen, unsubstituted or hydroxy-substituted C
1
-C
4
alkyl or a radical of formula (3), particularly preferably hydrogen, methyl, ethyl or &bgr;-hydroxyethyl or a radical (3) and, very particularly preferably, hydrogen or a radical (3), wherein B, D, R
2
and R
3
have the meanings cited above. In a very particularly preferred embodiment of this invention, R is a radical of formula (3).
R
1
is preferably hydrogen or C
1
-C
4
alkyl, particularly preferably hydrogen, methyl or ethyl and, very particularly preferably, hydrogen.
R
2
is preferably carbamoyl or sulfomethyl, more preferably carbamoyl.
R
3
defined as C
1
-C
4
alkyl is, for example, methyl, ethyl, n- or isopropyl or n-, sec-, tert- or isobutyl, preferably methyl or ethyl.
R
3
is preferably methyl or ethyl, more preferably methyl.
R
2
is preferably carbamoyl or sulfomethyl, more preferably carbamoyl, and R
3
is C
1
-C
4
alkyl, more preferably methyl.
The aliphatic linking group B is, for example, straight-chain or branched C
2
-C
12
alkylene which is unsubstituted or substituted by hydroxy, C
1
-C
4
alkoxy, sulfato or sulfo and/or interrupted once or several times by —O— or —NR
4
—, wherein R
4
is hydrogen or C
1
-C
4
alkyl, preferably hydrogen, methyl or ethyl, particularly preferably hydrogen. B is preferably straight-chain or branched C
2
-C
6
alkylene which is unsubstituted or substituted by hydroxy, sulfo or sulfato and, particularly preferably, unsubstituted straight-chain or branched C
2
-C6alkylene. Examples of particularly preferred linking groups B are 1,2-ethylene, 1,3-propylene, 2-hydroxy-1,3-propylene, 1,4-butylene, 2-methyl-1,5-pentylene, 1,6-hexylene, particularly preferably 1,2-propylene and 1,2-ethylene and, very particularly preferably, 1,2-ethylene.
X
1
defined as halogen is e.g. fluoro, chloro or bromo.
X
1
defined as C
1
-C
4
alkoxy is suitably, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy and, particularly preferably, methoxy.
X
1
defined as C
1
-C
4
alkylthio is, for example, methylthio, ethylthio, n-propylthio, isopropylthio or n-butylthio, preferably ethylthio or n-propylthio. The cited radicals are unsubstituted or substituted in the alkyl moiety by hydroxy, carboxy or sulfo. The substituted radicals are preferred.
X
1
defined as unsubstituted or substituted amino is amino which is unsubstituted or substituted at the N-atom, for example the following radicals:
N-mono- or N,N-di-C
1
-C
4
alkylamino, which encompasses both the unsubstituted radicals and the radicals which are substituted in the alkyl moiety, for example by C
1
-C
4
alkoxy, hydroxy, carboxy, sulfo or sulfato; the radicals substituted in the alkyl moiety being preferred;
C
5
-C
7
cycloalkylamino, which encompasses both the unsubstituted radicals and the radicals which are substituted in the cycloalkyl ring, for example by C
1
-C
4
alkyl, preferably methyl; of such radicals the corresponding cyclohexyl radicals are preferred;
phenylamino or N—C
1
-C
4
alkyl-N-phenylamino, which encompasses both the unsubstituted radicals and the radicals which are substituted in the phenyl ring, for example by C
1
-C
4
alkyl,
C
1
-C
4
alkoxy, halogen, carboxy or sulfo; these radicals are preferably unsubstituted or sulfo-substituted in the phenyl ring.
X
1
defined as a N-heterocycle which may contain further heteroatoms is suitably, for example, morpholino or piperidin-1-yl.
X
1
is preferably fluoro or chloro.
The group U which may be removed with alkali is suitably, for example, —Cl, —Br, —F, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OPO
3
H
2
, —OCO—C
6
H
5
, —OSO
2
—C
1
-C
4
alkyl or —OSO
2
—N(C
1
-C
4
alkyl)
2
. U is preferably a group of formula —Cl, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OCO—C
6
H
5
or —OPO
3
H
2
, more preferably —Cl or —OSO
3
H and, particularly preferably —OSO
3
H.
Examples of suitable radical

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