EP0205607A1 - Improvements in or relating to organic compounds - Google Patents

Abstract

New water-soluble and fiber-reactive compounds have the formula (I), in which the symbols have the definition given in claim 1, provided that a compound having the formula (I) contains at least one of the groups following: a) hydroxyl groups, b) ethers groups, c) carbonyl groups, d) carboxyl groups, these groups being present in the compounds of formula (II) and / or in R. These compounds are prepared in the manner conventional by condensation of a Qa-Hal compound with an appropriate initiator compound containing a primary or secondary amine group. The compounds having the formula (I) are useful as fiber-reactive dyes for dyeing or printing organic substrates containing nitrogen or hydroxyl groups, especially cotton. The preferred dye temperature is within the range of cold dye. The dyes and printed patterns thus obtained have good general solidity properties and are stable under any form of oxidizing influence.

Description

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

The invention relates to water-soluble compounds containing a fibre-reactive group which compounds are suitable as dyestuffs in conventional dyeing and printing processes. Their dyeings and prints are resistant to any oxidative influences.

According to the invention there is provided a compound corresponding to formula I

in which each of F₁ and F₂ is independently a water-soluble organic dyestuff radical, each Y is independently -O- or , each B is independently a divalent bridge member, m is independently 0 or 1 , each R is independently hydrogen, alky! or substituted alkyl, n is 0, 1 or 2, each Q is independently hydrogen, alkyl, substituted alkyl or a cellulose fibre-reactive group, provided that at least one of the two possible groups Q is a cellulose fibre- reactive group;

B is a divalent bridge member,

R₁ is alkyl or substituted alkyl, p is 0 or 1,

B₂ is a tri- or tetravalent bridge member, Q_a i s a cellulose fibre-reactive group, r is 1 or 2, q is 0 or 1, whereby n + q is at least 1, and q is 0 if n is 1 or 2, provided that a compound of formula I contains at least one of the groups listed below,

(a) hydroxy groups

(b) ether groupings

(c) carbonyl groups

(d) carboxy groups which is present in one of the groups -Y-B- ; -Y-B₁-R₁ ; and R, respectively, and salts of a compound of formula I.

F₁ and F₂ are preferably an organic dyestuff radical of the metal-free or metallised mono-, dis- or polyazo, anthraquinone, phthalocyanine, oxazine, dioxazine, nitro or formazan series which contains water-solubilising groups. Particularly preferred are dyestuff radicals belonging to the metal-free or metallised mono- or disazo series. Any fibre-reactive group as A or Q_a is preferably one of the following groups Q₁ to Q_{5 : -}

The group Q₁ is most preferred.

In the specification, in any hydroxysubstituted alkyl group which is attached to a nitrogen atom, the hydroxy group is bound to a carbon atom other than to the C₁-atom.

Any alkyl as R is preferably linear or branched C_1-4alkyl. More preferably it is methyl or ethyl, especially methyl.

Any substituted alkyl as R is preferably a monohydroxysubstituted C_{2 -8}alkyl group, a dihydroxysubstituted C₃-₈alkyl group, or More preferably it is a monohydroxysubstituted C_2-4alkyl group, dihydroxysubstituted Chalkyl or -CH₂CH₂OCH₂CH₂OH. Most preferably it is 2-hydroxyethyl or 2,3-dihydroxypropyl.

R is preferably R_a, where R_a is hydrogen, methyl, ethyl, monohydroxy-C_2-8alkyl, dihydroxy-C_3-8alkyl, or More preferably R is R_b, where R_b is hydrogen, methyl, monohydroxy-C_2-4alkyl, dihydroxy-C_3-4alkyl or

-CH₂CH₂OCH₂CH₂OH. Even more preferably it is R_c, where R_c is hydrogen, -CH₂CH₂OH, or -CH₂CH₂OCH₂CH₂OH. Most pre ferably, R is R_d, where R_d is hydrogen or -CH₂CH₂OH.

Y is preferably -O- , -NH- or ; especially -NH-.

Any alkyl as Q is straight chain or branched; any unsubstituted alkyl preferably contains 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms. Any substituted alkyl as Q is preferably monohydroxysubstituted C_2-4alkyl, dihydroxysubstituted C_3-4alkyl or -CH₂CH₂OCH₂CH₂OH.

The group (Q_a) preferably signifies either the group , more preferably the group ,

especially the group -NH-Q_a, in which groups Q_a is most preferably Q₁; or the group -NH-Q_d, in which Q_d is hydrogen, monohydroxy- C_2-4alkyl, dihydroxy-C_3-4alkyl or -CH₂CH₂OCH₂CH₂OH; more preferably Q_d is hydrogen or -C_H2CH₂OH.

B is preferably a chain-type, linear or branched bridge member or a bridge member which is branched by a cycloaliphatic, aromatic or heteroaromatic ring system, which bridge members additionally contain at least one of the above-listed groups (a) to (d), especially a hydroxy or carbonyl group thereof.

If B is a chain-type bridge member, it preferably denotes mono- or dihydroxysubstituted C_3-6alkylene or -CO(CH₂)_1-3-; especially , or -COCH₂-.

Any branching in B preferably takes place through a heteroaromatic ring system, especially through triazine rings.

More preferably is a group of the formula

in which

Q_b is hydrogen, alkyl, substituted alkyl or one of the groups Q₁ to Q₅ as defined above,

R₂ is chlorine, or -OR₅ , each R₃ is independently hydrogen, alkyl or substituted alkyl,

R₅ is monohydroxysubstituted C_2-6alkyl, di- or polyhydroxy- substituted C_3-8alkyl, or and

R₄ is (i) monohydroxysubstituted C_2-6alkylene or di- or polyhydroxysubstituted C_3-8alkylene,

(ii) C_2-6alkylene or,

(iii) together with the groups -NR₃-(wherein R₃ is hydrogen) to which R₄ is attached, forms a piperazine ring,

provided that in case of (ii) and (iii), R₂ is defined as .

More preferably R₄ is a group as defined under (i) or (ii). R₁ is preferably monohydroxy-C_2-4alkyl, dihydroxy-C_3-8alkyl, more preferably, R₁ is -CH₂CH₂OH or -CH₂CH(OH)CH₂OH.

B₁ is preferably a C_3-6alkyleneamine group which is linear or branched and may be substituted by one or two hydroxy groups, or is -CO(CH₂)_1-5 NH-. Most preferably, B ₁ is or -CO(CH₂)_1-5NH-.

B₂ is preferably a tri- or tetravalent, especially trivalent bridge member containing triazine rings. Particularly, -B₂-NH-Q_a is a group of formula (a),

in which R₂, R₃ and R₄ are as defined above, and Q_c is one of the groups Q₁ to Q₅ as defined above.

Particularly preferred are compounds of formula I corresponding to formula la (with p and q = 0; m = 1 and n = 1 or 2); formula lb (with m, p and q = 0 and n = 1 or 2); formula Ic (with n and p = 0 and q = 1); and formula Id (with m and q = 0 and n and p = 1): -

Compounds of formula la,

in which

B_a is mono- or dihydroxysubstituted C₃_₆alkylene or

-CO(CH₂)_1-3- ; more preferably it is or -COCH₂- , and

R is R_a or

in which is a group

wherein R₂, R₃, R₄ and Q_b are as defined above, and R₄ is more preferably a group as defined under (i) or (ii), provided that at least one of the two possible Q or Q_b is a fibre-reactive group; and in which a) in the case where n is 1, F₁-NH- has one of the following preferred significances: -

wherein t is 0 or 1 ;

wherein t is 0 or 1 , and subst. is H, CH₃, OCH₃ or NHCOCH₃;

wherein each t is independently 0 or 1 , the sulpho group is in position 3 or 4;

S₁ is H, CH₃, OCH₃, NHCOCH₃ or NHCONH₂, S₂ is H or OCH₃;

b) in the case where n is 2, - has the following preferred significance: -

in which formula each of the -NH- groups is independently in the 4- or 5-position; in which compounds of formula la both groups may be the same or different and in particular, only one of both groups Q is a fibre-reactive group.

Compounds of formula lb,

in which R is preferably R_b, and more preferably R_c, and in the case where n is 1, as well as in the case where n is 2, the same definitions apply to F₁ as given for the compounds of formula la.

Compounds of formula Ic,

in which -B₂ -NH-Q_a is a group of formula (a'),

R₂, R₃, R₄ and Q_aare as defined above, and F₁ and F₂ have one of the following preferred significances: - a) F₁-NH- is a group of the formula,

and F₂-NH- is a group of the formula,

b) F₁-NH- is a group of the formula,

and F₂-NH- is a group of the formul,,

in which each t is independently 0 or 1 and each sulpho group is independently in the 3- or 4-position, each S₁ is independently H, CH₃, OCH₃, NHCOCH₃ or NHCONH₂, and each S₂ is independently H or OCH₃.

Compounds of formula Id,

in which Q_a is as defined above, Y is -O- or -NH-,

B₁ is NH- or -CO(CH₂)₁_₅ NH- , and R₁ is monohydroxysubstituted C_2-4alkyl, dihydroxysubstituted C_3-8alkyl, i^s a group of the formula,

in which each t is independently 0 or 1 and the sulpho group is in the 3- or 4-position,

S₃ is H or CH₃ and S₄ is -O-B₁-R₁ or

S₃ is -NH-B₁-R₁ and S₄ is H.

Preferably, in a compound of formulae la to Id, the fibre- reactive group is Q₁.

When a compound of formula I containing sulpho and/or carboxy groups is in the salt form, the cation of any sulpho and carboxy groups is not critical and may be any of those non-chromophoric cations conventional in the field of reactive dyestuffs provided that the corresponding salts as obtained are water-soluble. Examples of such cations are alkali metal cations and unsubstituted or substituted ammonium cations, e.g., lithium, sodium, potassium, ammonium, mono-, di-, tri- and tetra-methylammonium, triethyl-ammonium, mono-, di- and tri-ethanolammonium.

The preferred cations are the alkali metal cations and ammonium, with sodium being the most preferred.

In a compound of formula I the cations of any sulpho and carboxy groups can be the same or different, i.e. they can also be a mixture of the above mentioned cations meaning that the compound of formula I can be in a mixed salt form.

The present invention further provides a process for the preparation of the compounds of formula I comprising reacting a compound of formula II,

in which

R_x is hydrogen, alkyl or substituted alkyl, and each n' is independently 0 or 1 , with a compound of formula II^I,

Q_a—Hal III in which Q_a is a cellulose fibre-reactive group, and

Hal is halogen,

using the corresponding amount of a compound of formula III necessary to "introduce 1 or 2 groups Q_a per molecule of a compound of formula II,

This condensation may be effected in accordance with conventional methods.

The compounds of formula I may be isolated in accordance with known methods, for example, by conventional salting out with alkali metal salts, filtering and drying in vacuo.

Depending on the reaction and isolation conditions a compound of formula I containing sulpho and/or carboxy groups is obtained in free acid or preferably salt form or even mixed salt form containing, for example, one or more of the above-mentioned cations. It may be converted from free acid form to a salt form or mixtureof salt forms or vice versa or from one salt form to another by conventional means.

The starting compounds of formula II are known with regard to their chromophoric part. In order to introduce into the compounds of formula II those groups containing one or more of the groups (a) to (d) according to the invention, various ways of preparation may be used. All these methods concern processes known per se which therefore are analogous preparation processes.

For example, the following principles of synthesis are possible: -

(1) Preparation of compounds of formula II of type

in which Y is -NR- and B is a triazine bridge of the formula

comprising the following steps

(1a) reacting a compound F₁-NHR with cyanuric chloride;

(1b) subsequently,reacting the resulting condensation product with a hydroxy group containing amino compound;

(1c) subsequently, reacting with a hydroxy group containing diamino compound.

Similarly, compounds of formula II corresponding to type

in which B₂ is a group

may be prepared using in step (1a), instead of cyanuric chloride, the condensation product consisting of two cyanuric chloride radicals linked together by a bridge; the process is otherwise effected in analogous manner.

(2) Preparation of compounds of formula II of type F₁— Y—B—NHR

in which Y is -O- or -NR-, B is hydroxysubstituted alkylene and R is hydrogen or substituted alkyl, comprising the following steps (2a) reaction of F₁-NHR or F₁-OH with a bifunctional chlorohydrin such as epichlorohydrin;

(2b) subsequent reaction with a hydroxy group containing amino compound.

(3) Preparation of compounds of formula II of tpye F₁—Y—B—NHR in which Y is -NH- and B is -CO(CH₂)—_1-5 , comprising the steps

(3a) reaction of F₁-NH₂ with an α-chloro-acid chloride such as chloroacetic acid chloride; (3b) subsequent reaction with a hydroxy group containing amino compound.

(4) Preparation of compounds of formula II of tpye

in which Y is -O- or -NH-, B₁ is hydroxysubstituted alkylene or -CO(CH₂)—_1-5 and R₁ is hydroxysubstituted alkyl, comprising the steps

(4a) reaction of or

in which S is a protecting group, either with a bifunctional chlorohydrin such as epichloro hydrin, or with an α-chloro-acid chloride such as chloroacetic acid chloride;

(4b) subsequent reaction with a hydroxy group containing amino compound; (4c) splitting off the protecting group.

The compounds of formula I and mixtures thereof are useful as fibre-reactive dyestuffs for dyeing or printing hydroxy group or nitrogen containing organic substrates. Preferred substrates are leather and fibre materials containing or consisting of natural or synthetic polyamides and, particularly, of natural or regenerated cellulose such as cotton, viscose and spun rayon. The most preferred substrate is textile material containing or consisting of cotton.

Dyeing or printing is effected in accordance with known methods conventional in the reactive dyestuff field. Especially preferred is the exhaust dyeing method. The most favourable and therefore preferred dyeing temperature is within the cold-dyeing range of from 30 to 60°C.

The compounds of this invention are well compatible with other reactive dyes; they may be applied per se or in combination with appropriate fibre-reactive dyestuffs of the same class having analogous dyeing properties, e.g., concerning common fastness properties, extent of ability to exhaust from the dyebath onto the fibre etc. The dyeings obtained with such combination mixtures have good fastness properties and are comparable to those obtained with a single dyestuff.

In view of their good build-up power the compounds of formula I give high exhaust and fixation yields. The dyeings and prints obtained show particularly good light fastness, but also good wet fastness properties such as fastness to washing, water, sea water and sweat. In particular, the present dyestuffs give dyeings and prints which show good resistance to any oxidative influences, e.g., chlorinated water, hypochlorite bleach and peroxide or perborate containing wash liquors.

The following examples further serve to illustrate the invention. In the examples all parts and percentages are by weight or volume. The temperatures are in degrees Centigrade.

Example 1

18.5 Parts of cyanuric chloride are added to a mixture of 70 parts of water and 70 parts of ice. A solution of 57.2 parts of a compound of the formula

in the trisodium salt form (having a pH of approximately 7) is added to the suspension obtained. Stirring is effected at pH 5.5-6.5 until any free amino group is no longer detectable. Subsequently, 10.5 parts of diethylene glycole amine are added. The mixture is heated to 40°, and stirring is effected for one hour. During the reaction, the pH is kept at 7.0-7.5 by adding dilute sodium carbonate solution. To this reaction mixture 18 parts of 1,3-diaminopropanol-2 are then added. The mixture is stirred at 50° during four hours, whereby a pH in the range of 10.0-10.5 is kept by adding sodium hydroxide solution.

The dyestuff thus obtained is salted out using an appropriate amount of sodium chloride, and is filtered off. 13.5 Parts of 5-chloro-2,4,6-trifluoropyrimidine are added to the dye paste which is dissolved in 900 parts of water. Stirring is effected for two hours at 30-40°, and the pH is kept at 5-6 by adding dilute sodium carbonate solution. The obtained dyestuff is salted out with sodium chloride and isolated in conventional manner, it corresponds, in free acid form, to the formula

The dyestuff when dried is a dark-red powder which dissolves in water in a red colour. This dyestuff dyes cotton a red shade. The dyeings obtained show good light and wet fastness properties, especially they are stable to any oxidative influences.

Examples 2 to 134

By analogy with the method described in Example 1 further compounds of formula I may be prepared which are listed in the following Tables 1 to 5. Concerning the preparation processes with respectto the used starting materials, intermediate compounds prior to introducing the fibre-reactive group, reference is made to the corresponding passages in the description.

Examples 2 to 64

The compounds are listed in Table 1; they correspond to formula IV,

in which the symbols are as defined in Table 1. Examples 65 to 88

The compounds are listed in Table 2; they correspond to formula V,

in which the symbols are as defined in Table 2. Examples 89 to 109

The compounds are listed in Table 3; they correspond to formula VI,

in which the symbols are as defined in Table 3. Examples 110 to 118

The compounds are listed in Table 4; they correspond to formula VII,

in which the symbols are as defined in Table 4. Examples 119 to 134

The compounds are listed in Table 5; they correspond to formula VIII,

in which the symbols are as defined in Table 5. Cellulose fibres may be dyed with the dyestuffs listed in the tables, in particular using the conventional exhaust dyeing method. In column I of each of the Tables 1 to 4 the shade of the dyeing on cotton is given, whereby a is greenish-yellow h is bluish-red b is yellow i is ruby c is golden-yellow j is violet d is orange k is blue e is red-orange l is greenish-blue f is scarlet m is turquoise g is red n is navy.

The cotton dyeings obtained with the compounds of Table 5 are all reddish-yellow.

Generally, the resultant cotton dyeings have good light and wet fastness properties, they are especially resistant to any oxidative influences.

27

Further compounds of formula I which may be prepared by analogous method as described in Example 1 are given by the following examples :-

Examples 135 and 136

The compounds correspond to the formula

i n which for Example 135, X is -NHCH₂CH₂OH; for Example 136, X is each of them dyes cotton a navy shade.

Example 137

The compound corresponds to the formula

and dyes cotton a bluish-red shade.

In the following list maximum absorption wavelengths (α_max. in nm) as available for the exemplified dyestuffs are given. The values were determined using an aqueous solution of the dyestuffs.

Ex.No. α_max.(nm) Ex.No. α_max.(nm) α_max.(nm)

1 540 33 503 75 505

2 542 34 506 76 496

3 545 35 485 78 541

4 545 36 482 80 606

5 542 37 515 81 605

6 515 38 496 82 606

7 512 39 498 83 514

8 512 40 600 84 515

9 515 41 384 85 485

10 402 42 386 86 487

11 404 43 492 87 485

12 405 44 493 88 485

13 402 47 555 119 384

14 418 50 540 120 384

15 416 53 596 121 382

16 416 54 606 122 382

17 400 55 606 123 381

18 402 56 604 124 382

19 401 57 606 125 384

20 401 58 607 126 383

21 424 59 606 127 384

22 426 60 604 128 383

23 426 65 541 129 382

24 424 66 516 130 382

25 418 67 515 131 381

26 410 68 402 132 382

27 496 69 401 133 384

28 495 70 400 134 384

29 496 71 424 135 605

30 497 72 496 136 606

31 505 73 497 137 512

32 503 74 506 In accordance with the method as described the dyestuffs of Examples 1 to 137 are obtained in the sodium salt form. They may, depending on the reaction/isolation conditions or by reacting the sodium salts in accordance with known methods, also be obtained in free acid form or in other salt forms, for example those salt forms containing one or more cations indicated in the description above.

In the following examples the application of the compounds of this invention is illustrated.

Application Example A (exhaust dyeing)

0.3 Parts of the dyestuff of Example 1 or 135 are dissolved in 300 parts of demineralised water and 15 parts of Glauber's salt (calcined) are added. The dyebath is heated to 40°, then 10 parts of cotton fabric (bleached) are added. After 30 minutes at 40°, 6 parts of sodium carbonate (calcined) are added to the bath portionwise every 10 minutes applying quantities of 0.2, 0.6, 1.2 and finally 4.0 parts thereof. During the addition of sodium carbonate the temperature is kept at 40°. Subsequently, dyeing is effected for a further one hour at 40°. The dyed fabric is then rinsed with running cold water for 3 minutes and afterwards with running hot water for a further 3 minutes. The dyeing is soaped at the boil for 15 minutes in 500 parts of demineralised water and 0.25 parts of sodium lauryl sulphonate. After rinsing with running hot water (for 3 minutes) and centrifuging, the dyeing is dried in a cabinet dryer at ca. 70°. A red (navy) cotton dyeing is obtained which shows good light fastness and wet fastness properties and which is resistant to any oxidative influences. Application Example B (printing)

A printing paste consisting of

40 parts of the dyestuff of Example 6 or 38

100 parts of urea 340 parts of water

500 parts of a 4% sodium alginate thickener and

20 parts of sodium carbonate

1000 parts

is applied to cotton fabric in accordance with a conventional printing method.

The printed fabric is dried and fixed in steam at 105° for one minute. It is then rinsed in hot water, soaped at the boil (according to the method described in Application Example A) and dried. A red (red-orange) print is obtained which has good general fastness properties and is stable to any oxidative influences.

Similarly, the dyestuffs of the other examples or mixtures of the dyestuffs of Examples 1 to 137 may be employed to dye or print cotton in accordance with the method given for Application Examples A and B.

Claims

CLAIMS: -

1. A compound which corresponds to formula I,

and salts thereof, in which each of F₁ and F₂ is independently a water-soluble organic dyestuff radical, each Y is independently -O- or , each B is independently a divalent bridge member, m is independently 0 or 1, each R is independently hydrogen, alkyl or substituted alkyl, n is 0, 1 or 2, each Q is independently hydrogen, alkyl, substituted alkyl or a cellulose fibre-reactive group, provided that at least one of the two possible groups Q is a cellulose fibre- reactive group;

B is a divalent bridge member,

R₁ is alkyl or substituted alkyl, p is 0 or 1,

B₂ is a tri- or tetravalent bridge member, Q_a is a cellulose fibre-reactive group, r is 1 or 2, q is 0 or 1, whereby n + q is at least 1, and q is 0 if n is 1 or 2, provided that a compound of formula I contains at least one of the groups listed below, —

(a) hydroxy groups

(b) ether groupings

(c) carbonyl groups

(d) carboxy groups which is present in one of the groups -Y-B- ; -Y-B₁-R₁ ; and R, respectively.

2. A compound according to Claim 1, in which each of F₁ and F₂ is independently a water-soluble dyestuff radical of the metalfree or metallised mono-, dis- or polyazo, anthraquinone, phthalocyanine, oxazine, dioxazine, nitro or formazan series.

3. A compound according to Claim 1 or 2, in which Q or Q_a is one of the following groups Q₁ to Q₅: -

in which X₁ is alkyl or halogen substituted alkyl;

in which X₂ is NH₂ or any amine group;

4. A compound according to any one of Claims 1 to 3, in which m is 1 and n is 1 or 2, Y is -NR- and -B-NR-Q is a group of the formula,

in which

Q_b is hydrogen, alkyl, substituted alkyl or is one of the groups Q₁ to Q₅ as defined in Claim 3, provided that at least one of the two possible Q_b is a fibre-reactive group,

R₂ is chlorine, or -OR₅,

R₃ is independently hydrogen, alkyl or substituted alkyl,

R₅ is monohydroxy substituted C_2-6alkyl, di- or polyhydroxy substituted C_3-8alkyl, and

R₄ is (i) monohydroxy substituted C_2-6alkylene or di- or polyhydroxy substituted C_3-8alkylene, (ii) C_2-6alkylene, or (iii) together with the groups -NR₃- to which R₄ is attached and in which R₃ is hydrogen, forms a piperazine ring, provided that in case of (ii) and (iii), R₂ is defined as

5. A compound according to any one of Claims 1 to 3, in which m is 1, n is 1 or 2 and p is 0, B is mono- or dihydroxy substituted C_3-6alkylene or -CO(CH₂)_1-3-,

Y is -O- or - NH-,

R is monohydroxy substituted C_2-8alkyl, dihydroxy substituted C_3-8alkyl, or , provided that at least one of the two possible Q is one of the groups Q₁ to Q₅ as defined in Claim 3.

6. A compound according to any one of Claims 1 to 3, in which m and p are 0 and n is 1 or 2, and R is monohydroxy substituted C_2-8alkyl, dihydroxy substituted C_3-8alkyl or

7. A compound according to any one of Claims 1 to 3, in which m and q are 0, p is 1 and n is 1 or 2, R is hydrogen,

Y is -O- or -NH-,

B₁ is or -CO(CH₂)_1-5-NH-, R₁ is monohydroxy substituted C_2-4alkyl, dihydroxy substituted C_3-8alkyl, provided that at least one of the two possible Q is one of the groups Q₁ to Q₅ as defined in Claim 3.

8. A compound according to any one of Claims 1 to 3, in which p and n are 0, q and r are 1,

Y is -NH-,

R is hydrogen and -B₂-NH-Q_a is a group (a),

in which R₂ is chlorine, or -OR₅, R₃ is independently hydrogen, alkyl or substituted alkyl, R₅ is monohydroxy substituted C_2-6alkyl, di- or polyhydroxy substituted C_3-8alkyl, or ( CH₂)_1-5-COOH, and

R₄ is (i) monohydroxy substituted C_2-6alkylene or di- or polyhydroxy substituted C_3-8alkylene, (ii) C_2-6alkylene, or

(iii) together with the groups -NR₃- to which R₄ is attached and in which R₃ is hydrogen, forms a piperazine ring, provided that in case of (ii) and (iii), R₂ is defined as and

Q_c is one of the groups Q₁ to Q₅ as defined in Claim 3.

9. A process for the preparation of a compound of formula I, defined in Claim 1, comprising reacting a compound of formula II,

in which

R_x is hydrogen, alkyl or substituted alkyl, and each n' is independently 0 or 1, with a compound of formula III,

Q_a-Hal III in which

Q_a is a cellulose fibre-reactive group, and

Hal is halogen, using the corresponding amount of a compound of formula III necessary to introduce 1 or 2 groups Q_a per molecule of a compound of formula II.

10. A process for dyeing or printing hydroxy group or nitrogen containing organic substrates comprising applying to the substrate a compound of formula I, according to any one of Claims 1 to 8, or a mixture thereof as dyeing or printing agent.