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EP0205607A1 - Composes organiques ameliores - Google Patents

Composes organiques ameliores

Info

Publication number
EP0205607A1
EP0205607A1 EP19860900670 EP86900670A EP0205607A1 EP 0205607 A1 EP0205607 A1 EP 0205607A1 EP 19860900670 EP19860900670 EP 19860900670 EP 86900670 A EP86900670 A EP 86900670A EP 0205607 A1 EP0205607 A1 EP 0205607A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
groups
formula
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19860900670
Other languages
German (de)
English (en)
Inventor
Günther AUERBACH
Werner Koch
Peter Matzinger
Jürg STEIGER
Hans Rudolf Von Tobel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of EP0205607A1 publication Critical patent/EP0205607A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • C09B62/4413—Non-metallized monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring

Definitions

  • 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.
  • each of F 1 and F 2 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
  • R 1 is alkyl or substituted alkyl, p is 0 or 1,
  • B 2 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,
  • F 1 and F 2 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 Q 1 to Q 5 : -
  • the group Q 1 is most preferred.
  • 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 1 -atom.
  • Any alkyl as R is preferably linear or branched C 1-4 alkyl. 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 C 3 - 8 alkyl group, or More preferably it is a monohydroxysubstituted C 2-4 alkyl group, dihydroxysubstituted Chalkyl or -CH 2 CH 2 OCH 2 CH 2 OH. Most preferably it is 2-hydroxyethyl or 2,3-dihydroxypropyl.
  • R is preferably R a , where R a is hydrogen, methyl, ethyl, monohydroxy-C 2-8 alkyl, dihydroxy-C 3-8 alkyl, or More preferably R is R b , where R b is hydrogen, methyl, monohydroxy-C 2-4 alkyl, dihydroxy-C 3-4 alkyl or
  • R c is hydrogen, -CH 2 CH 2 OH, or -CH 2 CH 2 OCH 2 CH 2 OH.
  • R d is hydrogen or -CH 2 CH 2 OH.
  • 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 2-4 alkyl, dihydroxysubstituted C 3-4 alkyl or -CH 2 CH 2 OCH 2 CH 2 OH.
  • the group (Q a ) preferably signifies either the group , more preferably the group ,
  • group -NH-Q a in which groups Q a is most preferably Q 1 ; or the group -NH-Q d , in which Q d is hydrogen, monohydroxy- C 2-4 alkyl, dihydroxy-C 3-4 alkyl or -CH 2 CH 2 OCH 2 CH 2 OH; more preferably Q d is hydrogen or -C H2 CH 2 OH.
  • 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.
  • B is a chain-type bridge member, it preferably denotes mono- or dihydroxysubstituted C 3-6 alkylene or -CO(CH 2 ) 1-3 -; especially , or -COCH 2 -.
  • Any branching in B preferably takes place through a heteroaromatic ring system, especially through triazine rings.
  • Q b is hydrogen, alkyl, substituted alkyl or one of the groups Q 1 to Q 5 as defined above,
  • R 2 is chlorine, or -OR 5 , each R 3 is independently hydrogen, alkyl or substituted alkyl,
  • R 5 is monohydroxysubstituted C 2-6 alkyl, di- or polyhydroxy- substituted C 3-8 alkyl, or and
  • R 4 is (i) monohydroxysubstituted C 2-6 alkylene or di- or polyhydroxysubstituted C 3-8 alkylene,
  • R 2 is defined as .
  • R 4 is a group as defined under (i) or (ii).
  • R 1 is preferably monohydroxy-C 2-4 alkyl, dihydroxy-C 3-8 alkyl, more preferably, R 1 is -CH 2 CH 2 OH or -CH 2 CH(OH)CH 2 OH.
  • B 1 is preferably a C 3-6 alkyleneamine group which is linear or branched and may be substituted by one or two hydroxy groups, or is -CO(CH 2 ) 1-5 NH-. Most preferably, B 1 is or -CO(CH 2 ) 1-5 NH-.
  • B 2 is preferably a tri- or tetravalent, especially trivalent bridge member containing triazine rings.
  • -B 2 -NH-Q a is a group of formula (a)
  • R 2 , R 3 and R 4 are as defined above, and Q c is one of the groups Q 1 to Q 5 as defined above.
  • B a is mono- or dihydroxysubstituted C 3 _ 6 alkylene or
  • R is R a or
  • R 2 , R 3 , R 4 and Q b 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 b is a fibre-reactive group; and in which a) in the case where n is 1, F 1 -NH- has one of the following preferred significances: -
  • t is 0 or 1 ;
  • t is 0 or 1 , and subst. is H, CH 3 , OCH 3 or NHCOCH 3 ;
  • each t is independently 0 or 1 , the sulpho group is in position 3 or 4;
  • S 1 is H, CH 3 , OCH 3 , NHCOCH 3 or NHCONH 2
  • S 2 is H or OCH 3 ;
  • 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.
  • 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 F 1 as given for the compounds of formula la.
  • R 2 , R 3 , R 4 and Q a are as defined above, and F 1 and F 2 have one of the following preferred significances: - a) F 1 -NH- is a group of the formula,
  • F 2 -NH- is a group of the formula
  • F 1 -NH- is a group of the formula
  • F 2 -NH- is a group of the formul,
  • each S 1 is independently H, CH 3 , OCH 3 , NHCOCH 3 or NHCONH 2
  • each S 2 is independently H or OCH 3 .
  • B 1 is NH- or -CO(CH 2 ) 1 _ 5 NH-
  • R 1 is monohydroxysubstituted C 2-4 alkyl, dihydroxysubstituted C 3-8 alkyl, i s a group of the formula
  • 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 1 -R 1 or
  • S 3 is -NH-B 1 -R 1 and S 4 is H.
  • the fibre- reactive group is Q 1 .
  • 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.
  • 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,
  • 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
  • Hal is halogen
  • 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.
  • 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.
  • various ways of preparation may be used. All these methods concern processes known per se which therefore are analogous preparation processes.
  • step (1a) 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.
  • S is a protecting group, either with a bifunctional chlorohydrin such as epichloro hydrin, or with an ⁇ -chloro-acid chloride such as chloroacetic acid chloride;
  • 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.
  • 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.
  • 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 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.
  • Cellulose fibres may be dyed with the dyestuffs listed in the tables, in particular using the conventional exhaust dyeing method.
  • 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.
  • the resultant cotton dyeings have good light and wet fastness properties, they are especially resistant to any oxidative influences.
  • X is -NHCH 2 CH 2 OH; for Example 136, X is each of them dyes cotton a navy shade.
  • 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.
  • 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.
  • a printing paste consisting of
  • 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.
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Des nouveaux composés solubles dans l'eau et fibro-réactifs ont la formule (I), dans laquelle les symboles ont la définition donnée dans la revendication 1, à condition qu'un composé ayant la formule (I) contienne au moins un des groupes suivants: a) groupes hydroxyles, b) groupes d'éthers, c) groupes carbonyles, d) groupes carboxyles, ces groupes étant présents dans les composés de la formule (II) et/ou en R. Ces composés sont préparés de la manière conventionnelle par condensation d'un composé Qa-Hal avec un composé initiateur approprié contenant un groupe amine primaire ou secondaire. Les composés ayant la formule (I) sont utiles comme colorants fibro-réactifs pour teindre ou imprimer des substrats organiques contenant de l'azote ou des groupes hydroxyles, spécialement du coton. La température préférée de teinture se situe dans la plage de la teinture à froid. Les teintures et motifs imprimés ainsi obtenus ont de bonnes propriétés générales de solidité et sont stables sous n'importe quelle forme d'influence oxydante.
EP19860900670 1984-12-31 1985-12-23 Composes organiques ameliores Withdrawn EP0205607A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3447891 1984-12-31
DE3447891 1984-12-31

Publications (1)

Publication Number Publication Date
EP0205607A1 true EP0205607A1 (fr) 1986-12-30

Family

ID=6254168

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19860900670 Withdrawn EP0205607A1 (fr) 1984-12-31 1985-12-23 Composes organiques ameliores

Country Status (3)

Country Link
EP (1) EP0205607A1 (fr)
JP (2) JPS62501371A (fr)
WO (1) WO1986004080A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH666298A5 (de) * 1984-12-31 1988-07-15 Sandoz Ag Faserreaktive monoazoverbindungen.
US5227476A (en) * 1987-01-14 1993-07-13 Sandoz Ltd. 2-(3,6,8-trisulfonaphth-2-ylazo)-5-[2-chloro-4-[2-(5-chloro-2,4-difluoropyrimid-6-ylamino)-2-methyl-ethyl]amino-1,3,5-triazin-6-ylamino]phenyl urea salts thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB952620A (en) * 1959-08-24 1964-03-18 Ici Ltd New pyrimidine azo dyestuffs
CH467838A (de) * 1961-02-07 1969-01-31 Bayer Ag Verfahren zur Herstellung metallfreier Azofarbstoffe
US3822263A (en) * 1967-09-01 1974-07-02 Bayer Ag Reactive anthraquinone dyestuffs containing a fluoropyrimidinyl group
US4007164A (en) * 1968-03-19 1977-02-08 Bayer Aktiengesellschaft Azo dyestuffs containing 6-fluoro-pyrimidinyl 4-reactive group
GB1272119A (en) * 1968-10-01 1972-04-26 Interquim Sa Ind Y Com New fibre-reactive halotriazine dyes, process for obtaining the same and process for dyeing textile fibres with said dyes
JPS596149B2 (ja) * 1976-05-31 1984-02-09 三菱電機株式会社 電流形インバ−タの転流コンデンサ電圧検出回路
EP0069703B1 (fr) * 1981-07-07 1986-04-23 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8604080A1 *

Also Published As

Publication number Publication date
JPS62501371A (ja) 1987-06-04
WO1986004080A1 (fr) 1986-07-17
JPS61162556A (ja) 1986-07-23

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