IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

Abstract: New water-soluble, fibre-reactive compounds correspond to formula (I) in which the symbols are as defined in Claim 1, provided that a compound of formula (I) contains at least one of the following groups: (a) hydroxy groups, (b) ether groupings, (c) carbonyl groups, (d) carboxy groups, which group(s) is (are) in the compounds of formula (II) and/or in R. These compounds are prepared in conventional manner by condensation of a compound Qa-Hal with an appropriate starting compound containing a primary or secondary amine group. The compounds of formula (I) are suitable as fibre-reactive dyes for dyeing or printing hydroxy group or nitrogen containing organic substrates, especially cotton. The preferred dyeing temperature is in the cold-dyeing range. The dyeings and prints obtained have good general fastness properties and are stable to any oxidative influences.

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 N - Q I R in which each of F, and F is independently a water-soluble organic dyestuff radical, R each Y is independently -0- or -N- , each B is independently a divalent bridge member, m is independently 0 or 1 , each R is independently hydrogen, alky! or substituted alkyl, n i s 0 , 1 or 2 , each Q is independently hydrogen, alkyl, substituted alkyl or a cellulose fibre-reacti e group, provided that at least one of the two possible groups Q is a cellulose fibre- reactive group; B is a divalent bridge member, R 1 i s alkyl or substituted alkyl, s 0 or 1, B 2 is a tri- or tetravalent bridge member, s a cellulose fibre-reactive group, s 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-B.-R. ; and R, respectively, and salts of a compound of formula I. F^ and F~ 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 Ca i s preferably one of the following groups Q, to Q 5 in which X. is alkyl or halogen- substituted alkyl ; in which X 2 is H 2 or any amine group; The group Q. 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 C.-atom. Any alkyl as R is preferably linear or branched C, 4 alkyl. More preferably it is methyl or ethyl, especially methyl. Any substituted alkyl as R is preferably a monohydroxy¬ substituted Chalky1 group, a dihydroxysubstituted C,_ 8 alkyl group, -fCH ? CH ? Q ), 1,_-3, -CCHH 2 CCHH 2 00HH or - CU,-} -C00H. More 2 1-5 preferably it is a monohydroxysubstituted C- .alkyl group, di- hydroxysubstituted Chalky1 or -CH 2 CH 2 0CH 2 CH 2 0H. Most preferably it is 2-hydroxyethyl or 2,3-dihydroxypropyl . R is preferably R a , where R is hydrogen, methyl, ethyl, a a monohydroxy-C 2 _ 8 al kyl , di hydroxy-C 3 _ 8 al kyl , — (rC ^C^O ■ _----- CH 2 CH 2 0H or "fCHg ) . f . COOH. More preferably R i s R, , where R, i s hydrogen , methyl , monohydroxy-C 2 _ 4 al yl , dihydroxy-C, 4 al ky1 or -CH 2 CH 2 0CH 2 CH 2 0H. Even more preferably it is R , where R c is hydrogen , -CH 2 CH 2 0H, or -CH 2 CH 2 0CH 2 CH 2 0H. Most pre- ferably, R is R . , where R , is hydrogen or -CrLCr OH. Y is preferably -0- , -NH- or -N- ; especial ly -NH- . CH 3 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 mono¬ hydroxysubstituted C 2 _ 4 alkyl, dihydroxysubstituted C- .alkyl or -CH 2 CH 2 0CH 2 CH 2 0H. The group -N-Q (CL) preferably signifies i a -e—ith—er- the group -Ni-Qa, , more preferably the group -Ni-Qa, , R c R d especially the group -NH-Qa. in which groups Qa, is most pre- ferably O^; or the group -NH-Q., in which Q, is hydrogen, onohydroxy- C 2 _ 4 alkyl, dihydroxy-C 3 _ 4 alkyl or -CH 2 CH 2 0CH 2 CH 2 0H; more preferably Q d is hydrogen or -Cr CrLOH. 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~ g alkylene or -CO(CHp)., especially -CH 2 CHCH 2 ~ , -CHCH 2 - or -C0CH 2 ~. OH CH 2 OH Any branching in B preferably takes place through a hetero- aromatic ring system, especially through triazine rings. R More preferably -B-N-Q is a group of the formula in which Q, is hydrogen, alkyl, substituted alkyl or one of the groups Q. to Q 5 as defined above, R 2 is chlorine, -N-R 5 or -ORr , each R 3 is independently hydrogen, alkyl or substituted alkyl, R 5 is monohydroxysubstituted C 2 _ g a1kyl, di- or polyhydroxy- substituted C 3 _ 8 alkyl, -(-CH 2 CH 2 0) 1 _ 3 -CH 2 CH 2 0H or -( • CH 2 ) 1 _ 5 -C00H, and R 4 is (i) monohydroxysubstituted C 2 _ g alkylene or di- or polyhydroxysubstituted C 3 _ 8 alkylene, (ii) C 2 _ g alkylene or, (iii) together with the groups -NR 3 ~(wherein R 3 is hydrogen) to which R 4 is attached, forms a piperazine ring, provided that in case of (ii) and (iii), R 2 is defined as -N—R ς . More preferably R, is a group as defined under (i) or (ii). R , is preferably monohydroxy-C^al yl , dihydroxy-C 3 _ 8 al yl , -(-CH 2 CH 2 0) 1 _- 3 CH 2 CH 2 0H or more preferably, R ] is -CH 2 CH 2 0H or -CH 2 CH(0H)CH 2 0H. B, is preferably a C, g alkyleneamine group which is linear or branched and may be substituted by one or two hydroxy groups, or is -C0(CH 2 ) 1 _ 5 NH-. Most preferably, B 1 is -CH^CH^^NH- or -C0(CH 2 ) 1 _ 5 NH-. 0H B 2 is preferably a tri- or tetravalent, especially trivalent bridge member containing triazine rings. Particularly, -B^-NH-Q., 1 c. a is a group of formula (a), in which R 2 , R 3 and R 4 are as defined above, and Q is one of the groups Q, to Q 5 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, i n which B is mono- or dihydroxysubstituted C 3 _ g alkylene or -C0(CH 2 ) 1 _ 3 - ; more preferably it is -CH 2 CHCH 2 - OH -CHCH 2 - or -C0CH 2 - , and CH 2 0H R is R. or in which -Ba-NI-Q is a group wherein R 2 , R 3 , R 4 and Q, are as defined above, and R 4 is more preferably a group as defined under (i) or (ii), provided that at least one of the two possible Q or Q. is a fibre-reactive group; and in which a) in the case where n is 1, F.-NH- has one of the following preferred significances: - S0 3 H wherein t is 0 or 1 ; wherein t is 0 or 1 , and subst. is H, CH 3 , OCH 3 or NHCOCH 3 ; indepen¬ e sulpho ion 3 or 4; 3 , NHC0CH 3 < b) in the case where n is 2, F.—NH) 2 - as 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 -B -N-Q may be the a i R 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. , and more preferably R , and in the case where n is 1, as well as in the case where n is 2, the same definitions apply to F, as given for the compounds of formula la. Compounds of formula Ic, F - NH — B _ NH _ Qa Ic NH-F 2 i n which -B -NH-Q 3 is a group of formul a (a 1 ) , i c. a R- 3 R 2 , R 3 , R 4 and Q are as defined above, and F, and F„ have one of the following preferred significances: - a) F.-NH- is a group of the formula. and F -NH- is a group of the formula, wherein t is 0 or 1 b) F.-NH- is a group of the formula, and F 2 ~NH- is a group of the formula, in which each t is independently 0 or 1 and each sulpho group is independently in the 3- or 4-position, each S, is independently H, CH 3 , 0CH 3 , NHC0CH 3 or NHC0NH 2 , and each S 2 is independently H or OCH.,. Compounds of formula Id, ~ \ R 1 Id F—NH-Q a in which Q is as defined above, Y is -0- or -NH-, a B 1 is -CH 2 CH(CH 2 ) 1 _ 3 NH- or -C0(CH 2 ) 1 _ 5 NH- , and R 1 is OH monohydroxysubstituted C 2 _ 4 alkyl, dihydroxysubstituted C 3 _ 8 alkyl, -(-CH 2 CH 2 0) 1 3 -CH 2 CH 2 0H or is a group of the formul a , in which each t is independently 0 or 1 and the sulpho group is in the 3- or 4-position, S 3 is H or CH 3 and S 4 is -O-B ^ -R, or S 3 is -NH-B 1 -R 1 and S 4 is H. Preferably, in a compound of formulae la to Id, the fibre- reactive group is Q,. 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 Λ is hydrogen, alkyl or substituted alkyl, and each n' is independently 0 or 1 , with a compound of formula III, ■ Hal III in which Qa is a cellulose fibre-reactive group, and Hal is halogen, using the corresponding amount of a compound of formula III nneecceessssaarryy ttoo "introduce 1 or 2 groups Qa, per molecule of a compound of formula II, This condensation may be effected in accordance with con¬ ventional 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 con¬ taining, for example, one or more of the above-mentioned cations. It may be converted from free acid form to a salt form or mixture of 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 F-_—Y— B—NHR in which Y is -NR- and B is a triazine bridge of the formula comprising the following steps (1a) reacting a compound F.-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 NHR in which Bp is a group -for? N - R 4 4 " N _~-τ Nr I N-R„ 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 F — Y- B-NHR 1 in which Y is -0- or -NR-, B is hydroxysubstituted alkylene and R is hydrogen or substituted alkyl, comprising the following steps (2a) reaction of F,-NHR or F.-OH with a bifunctional chloro- hydrin such as epichlorohydrin; (2b) subsequent reaction with a hydroxy group containing amino compound. (3) Preparation of compounds of formula II of tpye F -Y-B-NHR in which Y is -NH-'and B is -C0(CH 2 )^g , comprising the steps (3a) reaction of F.-NH 2 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 F r γ - B ι- R ι NH 2 in which Y is -0- or -NH-, B, is hydroxysubstituted alkylene or -C0(CH 2 )ττ 5 and R, is hydroxysubstituted alkyl, comprising the steps (4a) reaction of F,-0H or F.-NHp I I NH-S NH-S 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 chl oro- acetic 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 l,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-chl oro-2,4,6-tri fl uoropyrimidi ne are added to the dye paste which is dissolved in 900 parts of water. Stirring i s effected for two hours at 30-40° , and the pH is kept at 5-6 by adding di l ute sodium carbonate sol ution . The obtained dyestuff is salted out wi th sodium chloride and i solated in conventional manner, i t 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, espe¬ cially they are stable to any oxidative influences. Examples 2 to 134 By analogy with the method described in Example 1 further com¬ pounds of formula I may be prepared which are listed in the follow¬ ing Tables 1 to 5. Concerning the preparation processes with respect to the used starting materials, intermediate compounds prior to in- troducing the fibre-reactive group, reference is made to the corre¬ sponding passages in the description. Examples 2 to 64 The compounds are listed in Table 1; they correspond to for¬ in which the symbols are as defined in Table 1. Examples 65 to 88 The compounds are listed in Table 2; they correspond to for¬ in which the symbols are as defined in Table 2. Examples 89 to 109 The compounds are listed in Table 3; they correspond to for¬ mula VI , F ι-÷ γ - 8 V!^ VI R in which the symbols are as defined in Table 3. Examples -110 to 118 The compounds are listed in Table 4; they correspond to for¬ mula in which the symbols are as defined in Table 4. Examples 119 to 134 The compounds are listed in Table 5; they correspond to for¬ in which the symbol s are as defined in Table 5. Cel lul ose fibres may be dyed with the dyestuffs l i sted 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-yel low h is bl uish-red b is yel l ow i i s ruby c is golden-yel low j is vi olet d is orange k is blue e is red-orange 1 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 oxi- dative influences. Table 1 (compounds of formula IV) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) 27 Table 1 (continued) Table 2 (compounds of formula V) Table 2 (continued) Table 2 (continued) Table 3 (continued) Table 4 (compounds of formula VII) Table 5 (compounds of formula VIII) Table 5 (continued) Further compounds of formula I which may be prepared by ana¬ logous method as described in Example 1 are given by the following examples:- Examples 135 and 136 The compounds correspond to the formula in which for Example 135, X is -NHCH 2 CH 2 0H; for Example 136, X is -NHCH 2 CHCH 2 0H ; OH each of them dyes cotton a navy shade. Example 137 The compound corresponds to the formula and dyes cotton a bluish-red shade. I Inn tthhee ffoolllloowwiinngg lliisstt mmaaxxiimmuumm absorption wavelengths ( max ιn nm) as available for the exemplified dyestuffs are given. The values were determined using an aqueous solution of the dyestuffs. Ex.No. (nm) Ex.No. (nm) Ex.No. 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 .f 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 centr fuging, 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. Appl cation 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 o 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 F, and F 2 is independently a water-soluble organic dyestuff radical, R I each Y is independently -0- or -N- , 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, R- j is alkyl or substituted alkyl, p is 0 or 1, B 2 is a tri- or tetravalent bridge member, Q a is a cel lulose 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-B-.-R, ; and R, respectively. 2. A compound according to Claim 1, in which each of F, and F 2 is independently a water-soluble dyestuff radical of the metal- free or metallised mono-, dis- or polyazo, anthraquinone, phthalo¬ cyanine, oxazine, dioxazine, nitro or formazan series. 3. A compound according to Claim 1 or 2, in which Q or Q_ is one of the following groups Cu to Q 5 : - in which X, is alkyl or halogen substituted alkyl; in which X 2 is NH 2 or any a ine 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 Q, to Qc as defined in Claim 3, provided that at least one of the two possible Q. is a fi bre-reactive group, R 2 i s chl orine, -N i -R 5 c or -0R C 5, R 3 R 3 is independently hydrogen, alkyl or substituted alkyl, R 5 is monohydroxy substituted C 2 _ g a1ky1, di- or polyhydroxy substi¬ tuted C 3 _ 8 alky1,-^CH 2 CH 2 0) 1 _- 3 CH 2 CH 2 0H or -CH 2 ) 1 _ 5 -C00H, and R. is (i) monohydroxy substituted C 2 _ g a1ky1ene or di- or polyhydroxy substituted C 3 _ 8 alkylene, (ii) C 2 _ g alky1ene, or (iii) together with the groups -NR 3 - to which R, is attached and in which R 3 is hydrogen, forms a piperazine ring, provided that in case of (ii) and (iii), R 2 is defined as -N-R c . i 0 R 3 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 _ g a1ky1ene or -C0(CH 2 ), --, Y is -0- or - NH-, R is monohydroxy substituted C 2 _ 8 alkyl, dihydroxy substituted C 3 _ 8 a1kyl,-fCH 2 CH 2 0) 1 _- 3 CH 2 CH 2 0H or -{CH^^-COOH, provided that at least one of the two possible Q is one of the groups Q, to Q g 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 substi¬ tuted C 2 _ 8 a1ky1, dihydroxy substituted Chalky! or-jCH^-μ-gCOOH. 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 -0- or -NH-, B 1 is -CH 2 CH(CH 2 ) 1 _ 3 -NH- or -C0(CH 2 ) 1 _ 5 -NH-, OH R-, is monohydroxy substituted Chalky!, dihydroxy substituted C 3 _ 8 a1kyl, ' -fCH 2 CH 2 0) 1-3 -CH 2 CH 2 0H or -fCH^^-COOH, provided that at least one of the two possible Q is one of the groups Q-, to Q 5 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 -B 2 -NH-Q a is a group (a), - q < • > in which R 2 is chlorine, -N-Rg or -ORg, . R 3 R 3 is independently hydrogen, alkyl or substituted alkyl, R 5 is monohydroxy substituted C 2 _ g alky1, di- or polyhydroxy substi¬ tuted C 3 _ 8 a1kyl,-fCH 2 CH 2 0) 1 _ 3 -CH 2 CH 2 0H or ( CH^^-COOH, and R4 is (i) monohydroxy substituted C 2 _ g alkylene or di- or polyhydroxy substituted C 3 _ g a1kylene, (ii) C 2 _ g alkylene, or (iii) together with the groups -NR 3 - to which R, is attached and in which R 3 is hydrogen, forms a piperazine ring, provided that in case of (ii) and (iii), R ? is defined as -N-R c , and i R 3 Q is one of the groups Q, to Q g 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, i n whi ch R 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 a Hal is halogen, using the corresponding amount of a compound of formula III necessary to introduce 1 or 2 groups Qa, 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.

Inventors: AUERBACH GUENTHER, KOCH WERNER, MATZINGER PETER, STEIGER JUERG, VON TOBEL HANS RUDOLF, AUERBACH, GUENTHER, KOCH, WERNER, MATZINGER, PETER, STEIGER, JUERG, VON TOBEL, HANS, RUDOLF
Applicants: SANDOZ AG
Application year: 1985
Main classification: C09B62
IPC codes: C09B62, D06P1, D06P3