Reactive dyestuffs containing monohagenotriazine and...

Details Reactive dyestuffs containing monohagenotriazine and... Reactive dyestuffs containing monohagenotriazine and...

1999-10-26

2002-04-23

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Azo

C534S617000, C534S642000

Reexamination Certificate

active

06376656

ABSTRACT:

The invention relates to new bi- and polyfunctional reactive dyestuffs, their preparation and their use.
Although bifunctional reactive dyestuffs are known, for example, from DE-A-2 614 550, EP-A-70 807, EP-A-70 806 and EP-A-74 928 and tri- and tetrafunctional reactive dyestuffs are known, for example, from EP-A-395 951, the known reactive dyestuffs still have diverse disadvantages in terms of their use, for example too low a fixing yield.
The present invention relates to new reactive dyestuffs of the formula
wherein
D is the radical of an organic dyestuff from the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone or the nitroaryl series,
W denotes a direct bond or bridge member, in particular represents a direct bond,
R
1
denotes H or C
1
-C
4
-alkyl, which can be substituted, for example, by OR, OSO
3
H, SO
3
H, COOH or halogen,
R represents H, CH
3
or C
2
H
5
,
R
2
denotes C
1
-C
4
-alkyl, in particular methyl,
Z represents —CH
2
—CH
2
—OSO
3
H or —CH═CH
2
,
X represents F, Cl or Br and
n denotes 1 or 2.
The following statements apply to the alkyl, aryl, aralkyl, hetaryl, alkoxy, halogen and acylamino radicals mentioned in the present Application and to the bridge members:
Alkyl groups are understood as meaning, in particular, those having 1 to 4 C atoms, which can optionally contain substituents, for example halogen, such as Cl or Br, OH, CN, CO
2
H, SO
3
H or OSO
3
H.
Alkoxy radicals are understood as meaning, in particular, those having 1 to 4 C atoms.
Halogen is understood as meaning, in particular, chlorine or fluorine.
Acylamino radicals are understood as meaning, in particular, those having 1 to 4 C atoms, such as formylamino, acetylamino, propionylamino and n-butyrylamino.
Suitable bridge members W are, for example:
wherein R
w
represents hydrogen or alkyl, and Alkylene denotes an alkylene radical having 1 to 6 C atoms, where * identifies the atom or group bonded to the chromophore D.
Alkylene radicals which may be mentioned are:
The invention furthermore relates to the preparation of the reactive dyestuffs of the formula (I):
a) either by condensation of dyestuffs of the formula
wherein
D, W, R
1
and n have the abovementioned meaning, with n moles of trihalogenotriazines of the formula
 to give compounds of the formula
 and further condensation of the compounds of the formula (IV) with n moles of the components of the formula
R
2
—NH—CH
2
CH
2
—SO
2
—Z  (V),
wherein
R
2
and Z have the abovementioned meaning, or
b) in the reverse sequence, by condensation of trihalogenotriazines of the formula (III) with the components of the formula (V) to give the primary condensation products
wherein
R
2
and Z have the abovementioned meaning, and further condensation of n moles of the compounds of the formula (VI) with the dyestuffs of the formula (II) or
c) by condensation of suitable precursors with the trihalogenotriazines (III) and the components of the formula (V) or by condensation of suitable precursors with the primary condensation products of the formula (VI) and subsequent dyestuff synthesis.
The invention furthermore relates to a process for the preparation of compounds of the formula (V), characterized in that compounds of the formula
R
2
—NH—C
2
H
4
—S—C
2
H
4
—OH,
which are obtained by reaction of 3-alkyl-2-oxo-oxazolidinones of the general formula
with 2-mercaptoethanol, are converted by oxidation, in particular with H
2
O
2
, into compounds of the formula
R
2
—NH—C
2
H
4
—SO
2
—C
2
H
4
—OH
and these are then converted into compounds of the general formula (V) in the customary manner.
The condensations of the starting components with the trihalogenotriazines are carried out in aqueous or organic-aqueous media in the presence of acid-binding agents, regardless of the sequence. Depending on the nature of the starting components, the first stage of the condensation is carried out here in pH ranges of 2 to 8, preferably 3 to 7, and at temperatures of 0 to 40° C., preferably 0 to 25° C. Replacement of the second halogen atom of the triazine takes place in the pH range from 4 to 10, preferably 5 to 9, and in the temperature range from 0 to 60° C., preferably 0 to 30° C.
Acid-binding agents are, for example, carbonates, hydroxides or phosphates, such as sodium carbonate, sodium bicarbonate, dilute sodium hydroxide solution, di- or trisodium phosphate or sodium fluoride.
If the condensation or the dyestuff synthesis is to lead directly to a dyestuff solution or to a liquid dyestuff preparation, it may be advantageous to use lithium carbonates or lithium hydroxide, if appropriate together with solubilizing agents and/or stabilizing buffer systems. Other conversion reactions of the dyestuffs or precursors thereof, such as metallization reactions, sulphonations or introduction of acylamino groupings, can in general be carried out at any desired stages of the dyestuff syntheses.
Particularly useful dyestuffs from the anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone or nitroaryl series are water-soluble formazan, anthraquinone and phthalocyanine dyestuffs, and in particular those which contain sulphonic acid and/or carboxylic acid groups. The dyestuffs can be either metal-free or metal-containing, the copper, nickel, chromium and cobalt complexes being of preferred interest under the metal complexes.
Suitable dyestuff radicals D of this class or the dyestuffs containing amino groups on which the dyestuffs of the formula (I) are based are described in a very large number in the literature. Examples which may be mentioned here are:
EP-A 54 515, EP-A 69 703, EP-A 70 807, DE-3 222 726,
DE-A 2 650 555, DE-A 3 023 855, DE-A 2 847 938,
DE-A 2 817 780, GB-A 2 057 479, DE-A 2 916 715,
DE-A 2 814 206, DE-A 3 019 936, EP-A 45 488 and
Venkataraman: The Chemistry of Synthetic Dyes, Volume VI, Chapter II, pages 211-325, New York, London; 1972.
A radical which contains one or more groups which confer water-solubility, in particular sulpho groups, but no further fibre-reactive radicals being a particularly suitable radical of an organic dyestuff of this class.
Preferred dyestuffs are those of the following formula (1) to (8), wherein, in general, B′ comprises a radical of the formula
and R
1
, X, R
2
and Z have the abovementioned meaning
wherein
R
3
=H, methyl, methoxy or chlorine
R
4
=H or SO
3
H and
R
5
=H, methyl or ethyl
 wherein
B denotes a radical of the formula
 in which the substituents X, R
2
and Z have the above-mentioned meaning, and
 wherein
A represents an optionally substituted phenylene or an optionally substituted aromatic-aliphatic bridge member, or represents a straight-chain or branched C
1
-C
6
-alkylene which is optionally interrupted by groupings containing heteroatoms, such as NR
6
, O or S, and can be substituted by C
1
-C
6
-alkoxy, OSO
3
H, SO
3
H, COOR or halogen,
and wherein, within a bridge member A, the group NR
6
can also form a heterocyclic aliphatic ring with the group NR
1
, in particular
T
1
and T
2
=independently of one another H, Cl, Br, C
1
-C
2
-alkyl, OCH
3
, OC
2
H
5
, acylamino, C
1
-C
2
-alkoxycarbonyl,
R
6
and R
7
=independently of one another H or C
1
-C
4
-alkyl, which can be substituted by OR, OSO
3
H, SO
3
H, COOR or halogen,
R=H, CH
3
or C
2
H
5
.
wherein
Me=Cu or Ni,
Pc=the radical of a phthalocyanine,
u+v+w=3.4-4.0, with the proviso that
u=0.8-2.0,
v=0-1.0 and
w=1.0-3.0, and
A has the abovementioned meaning,
R
7
has the abovementioned meaning,
R
8
and R
9
=H or C
1
-C
2
-alkyl, which is optionally substituted by OH, OSO
3
H, SO
3
H or COOH.
wherein
v1 and w1=0 or 1, where w1 is not identical to v1,
R
10
and R
11
independently of one another are H, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, OH, halogen, COOH, NO
2
, SO
3
H, sulphonamido, C
1
-C
4
-alkylcarbonylamino, optionally sub

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