GB2036778A - Reactive dyes - Google Patents

Reactive dyes Download PDF

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Publication number
GB2036778A
GB2036778A GB7937989A GB7937989A GB2036778A GB 2036778 A GB2036778 A GB 2036778A GB 7937989 A GB7937989 A GB 7937989A GB 7937989 A GB7937989 A GB 7937989A GB 2036778 A GB2036778 A GB 2036778A
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unsubstituted
alkyl
amino
sulfonic acid
acid
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BASF SE
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BASF SE
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    • 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
    • C09B62/04—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 to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/085—Monoazo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)

Abstract

Novel reactive dyes in the form of the free acids have the general formula I <IMAGE> where X is chlorine or bromine, R<1> is hydrogen or C1-C4-alkyl, R<2> is hydrogen or unsubstituted or substituted C1-C4-alkyl and R<3> is phenyl which is unsubstituted or is monosubstituted or polysubstituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano, amino, dimethylamino, diethylamino, C1-C4-alkoxycarbonyl, carbamyl which is unsubstituted or N-monosubstituted or N,N-disubstituted by C1-C4- alkyl, sulfamyl which is unsubstituted or N-monosubstituted or N,N- disubstituted by C1-C4-alkyl, or hydroxysulfonyl, or R<3> is naphthyl which is unsubstituted or is monosubstituted or polysubstituted by hydroxysulfonyl, with the proviso that if R<2> is unsubstituted C1-C4-alkyl, any phenyl radical R<3> is substituted. The dyes of the formula are exceptionally suitable for dyeing cellulosic textile material, leather and polyamides.

Description

SPECIFICATION Reactive dyes The present invention relates to reactive dyes.
According to the invention there are provided compounds which in the form of the free acids have the general formula I
where X is chlorine or bromine, R1 is hydrogen or C,~4-alkyl, R2 is hydrogen or unsubstituted or substituted C,-C4-alkyl, and R3 is phenyl which is unsubstituted or is mono-substituted or polysubstituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano, amino, dimethylamino, diethylamino, C,-C4- alkoxycarbonyl, carbamyl which is unsubstituted or N-monosubstituted or N,N-disubstituted by C,-C4alkyl, sulfamyl which is unsubstituted or N-monosubstituted or N,N-disubstituted by C,-C4-alkyl, or hydroxysulfonyl, or R3 is naphthyl which is unsubstituted or is monosubstituted or polysubstituted by hydroxysulfonyl, with the proviso that if R2 is unsubstituted C1-C4-alkyl, any phenyl radical R3 is substituted.
Examples of unsubstituted and substituted alkyl radicals R2 are C2H5, C3H7, C4Hg, CH2C 6H5, C2H4CN, C2H40H and especially methyl.
A compound of the formula I may be prepared by reacting a diazonium compound of the amine of the formula
with a coupling component of the formula
The individual structural moieties of a dye of the formula I can also be combined with one another in a different sequence.
The reactions are known in principle. Details of suitable ways of performing the reactions may be found in the Examples, where parts and percentages are by weight, unless stated otherwise.
The dyes of the formula I are yellowish red and give brilliant dyeings, distinguished by good fastness characteristics, e.g. lightfastness and wetfastness, on cellulosic fibers. They are in the main intended for exhaustion dyeing at an elevated temperature (60-800 C) and, in some cases, for printing, as well as for use with leather and polyamides.
Particularly important compounds are those of the formula la
where B is phenyl which is unsubstituted or substituted by methyl, methoxy, chlorine, carboxyl or hydroxysulfonyl, or is sulfonaphthyl, and R4 is hydrogen or methyl.
EXAMPLE 1 A solution of 21.8 parts of 1 -naphthylamine-6-sulfonic acid in 300 parts of water is added to the condensation product of 23.9 parts of 2-amino-5-hydroxynaphthalene-7-sulfonic acid and 18.8 parts of cyanuric chloride. The mixture is heated at 4O-500C and the acylation is completed at pH 5, obtained by adding 6.8 parts of sodium bicarbonate. The reaction mixture is then cooled to 100C with ice, after which a diazo suspension obtained by diazotizing 37.5 parts of 2-aminonaphthalene-3,6,8-trisulfonic acid is introduced. The coupling is carried out at a temperature of, preferably, from 1 O-200C, the pH during coupling being kept at 6 by means of 16.8 parts of sodium bicarbonate.The dye is precipitated from a neutral solution by adding sodium chloride, and is dried. A reddish brown powder is obtained which dyes'c'otto'n iii fast'clear yellowish red hues.
EXAMPLE 2 18.8 parts of cyanuric chloride are condensed, in aqueous solution, with 23.9 parts of 2-amino-5 hydroxynaphthalene-7-sulfonic acid at OOC, the pH during the acylation being kept at 5 by means of 50 parts of 1 M sodium carbonate solution.
A solution obtained by dissolving 13.4 parts of 2-aminobenzoic acid in sufficient water to give 200 parts is then added to the reaction mixture, the temperature is raised to 400C and during the second condensation the pH is kept at 5 by means of 6.8 parts of sodium bicarbonate. 37.5 parts of 2 naphthylamine--3,6,8-tnsulfonic acid are diazotized in the conventional manner and introduced into the coupling component solution, which has been cooled to 1 OOC with ice. Coupling is carried out at a temperature of, preferably, from 1 0-200C whilst keeping the pH at 6 by means of 16.8 parts of sodium bicarbonate. The dye is precipitated from a neutral solution by adding sodium chloride, and is dried.
Another method of isolating the dye is to spray-dry the reaction mixture.
On cotton, the dye gives fast, clear, yellowish red hues.
Table 1 lists further dyes obtainable by the processes described in Examples 1 and 2.
No. Diazo component Coupling component Triazine Amine component Hue 3 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 3-Aminobenzoic acid yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 4 " " " 4-Aminobenzoic acid " 5 " " " 2-Aminobenzenesulfonic acid " 6 " " " 3-Aminobenzenesulfonic acid " 7 " " " 4-Aminobenzenesulfonic acid " 8 " " " 2-(N-Methylamino)benzoic acid " 9 " " " 3-(N-Methylamino)benzene- " sulfonic acid 10 " " " 2-Amino-4-sulfobenzoic acid " 11 " " " 2-Amino-5-sulfobenzoic acid " 12 " " " 1-Aminobenzene-2,5-di- " sulfonic acid 13 " " " 1-Aminobenzene-2,4-di- " aulfonic acid No.Diazo component Coupling component Triazine Amine component Hue 14 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 3-Amino-6-chlorobenzene- yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid sulfonic acid 15 " " " 3-Amino-4-chlorobenzene- " sulfonic acid 16 " " " 2-Amino-4-chlorobenzene- " sulfonic acid 17 " " " 2-Amino-5-chlorobenzene- " sulfonic acid 18 " " " 2-Amino-5-methylbenzene- " sulfonic acid 19 " " " 4-Amino-5-methylbenzene- " sulfonic acid 20 " " " 4-Amino-6-methylbenzene- " sulfonic acid 21 " " " 2-Amino-5-methoxybenzene- " sulfonic acid 22 " " " 3-Amino-6-methoxybenzene- " sulfonic acid No.Diazo component Coupling component Triazine Amine component Hue 23 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 2-Amino-4-methyl-5-chloro- yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid benzenesulfonic acid 24 " " " 2-Amino-4-chloro-5-methyl- " benzenesulfonic acid 25 " " " 3-Amino-4-hydroxybenzene- " sulfonic acid 26 " " " 2-Amino-5-chlorobenzoic acid " 27 " " " 3-Amino-6-chlorobenzoic acid " 28 " " " 2,4-Diaminobenzene- " sulfonic acid 29 " " " 2,5-Diaminobenzene- " sulfonic acid 30 " " " 3-Amino-6-acetylamino- " benzenesulfonic acid 31 " " " 4-Amino-6-acetylamino- " benzenesulfonic acid No. Diazo component Coupling component Triazine Amine component Hue 32 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 2-Aminotoluene-4,5- yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid disulfonic acid 33 " 2-N-Methylamino-5-hydroxy- " 3-Amino-benzene- " naphthalene-7-sulfonic acid sulfonic acid 34 " " " 2-N-Methylamino- " benzoic acid 35 " 2-Amino-5-hydroxy- " 1-Aminonaphthalene-6- " naphthalene-7-sulfonic acid sulfonic acid 36 " " " 1-Aminonaphthalene-5- " sulfonic acid 37 " " " 1-Aminonaphthalene-4- " sulfonic acid 38 " " " 1-Aminonaphthalene-3- " sulfonic acid 39 " " " 1-Aminonaphthalene-7- " sulfonic acid 40 " " " 1-Aminonaphthalene-3,6- " disulfonic acid No.Diazo component Coupling component Triazine Amine component Hue 41 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 1-Aminonaphthalene-3,7- yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid disulfonic acid 42 " " " 2-Aminonaphthalene-5- " sulfonic acid 43 " " " 2-Aminonaphthalene-6- " sulfonic acid 44 " " " 2-Aminonaphthalene-7- " sulfonic acid 45 " " " 2-Aminonaphthalene-5,7- " disulfonic acid 46 " 2-N-Methylamino-5-hydroxy- " 1-Aminonaphthalene-5- " naphthalene-7-sulfonic acid sulfonic acid 47 " " " 1-Aminonaphthalene-6- " sulfonic acid 48 " " " 2-Aminonaphthalene-6- " sulfonic acid EXAMPLE 49 The reaction solution of the secondary condensation product obtained from 23.9 parts of 2amino 5-hydroxynaphthailene-7-sulfonic acid, 18.8 parts of cyanuric chloride and 9.3 parts of aniline is cooled to 100C with ice and a suspension obtained by diazotizing 37.5 parts of 2-naphthylamine-3,6,8trisulfonic acid is introduced. Coupling is carried out at an elevated temperature, preferably 1 0-200C, whilst keeping the pH at 6 by means of 16.8 parts of sodium bicarbonate. The dye is precipitated from a neutral solution by introducing sodium chloride, and is dried. The dye can also be isolated by spray- - drying the reaction mixture. A brownish red powder is obtained, which dyes cotton in fast yellowish red hues.
Table 2 lists further dyes obtainable by the method described in Example 49.
No. Diazo component Coupling component Triazine Amine component Hue 50 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric acid N-Cyanoethylaniline yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 51 " " " N-Hydroxyethylaniline " 52 " " " N-Benzylaniline " 53 " " " N-Methyl-o-toluidine " 54 " " " N-Ethyl-o-toluidine " 55 " " " N-Butyl-o-toluidine " 56 " " " N-Butyl-m-toluidine " 57 " " " N-Cyanoethyl-m-toluidine " 58 " " " o-Toluidine " 59 " " " m-Toluidine " 60 " " " p-Toluidine " 61 " " Cyanuric chloride o-Chloroaniline " No.Diazo component Coupling component Triazine Amine component Hue 62 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride m-Chloroaniline yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 63 " " " p-Chloroaniline " 64 " " " o-Anisidine " 65 " " " m-Anisidine " 66 " " " p-Anisidine " 67 " " " 2,5-Dimethylaniline " 68 " " " 2,4-Diemthylaniline " 69 " " " 2,3-Dimethylaniline " 70 " " " 2,4-Dimethoxyaniline " 71 " " " 2,5-Dimethoxyaniline " 72 " " " 2,4-Dichloroaniline " 73 " " " 2,5-Dichloroaniline " No.Diazo component Coupling component Triazine Amine component Hue 74 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 3,4-Dichloroaniline yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 75 " " " 3,5-Dichloroaniline " 76 " " " 3-Chloro-4-methylaniline " 77 " " " 2-Methyl-4-chloroaniline " 78 " " " 2-Methyl-5-chloroaniline " 79 " " " 2-Chloro-5-methylaniline " 80 " " " 3-Chloro-4-methoxyaniline " 81 " " " 2-Methoxy-5-chloroaniline " 82 " " " 2-Methoxy-4-chloroaniline " 83 " " " 2-Methyl-4-methoxyaniline " 84 " " " 2-Methoxy-5-methylaniline " 85 " " " 3-Methoxy-4-methylaniline " No.Diazo component Coupling component Triazine Amine component Hue 86 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 2-Methoxycarbonylaniline yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 87 " " " 2-Ethoxycarbonylaniline " 88 " " " 2,5-Diethoxycarbonylaniline " 89 " " " 4-Methoxycarbonylaniline " 90 " " " 4-Ethoxycarbonylaniline " 91 " " " 4-Dimethylaminoaniline " 92 " " " 4-Diethylaminoaniline " 93 " " " 3-Acetylaminoaniline " 94 " " " 4-Acetylaminoaniline " 95 " " " 2-Cyanoaniline " 96 " " " 4-Cyanoaniline " 97 " " " 4-Ethoxyaniline " No. Diazo component Coupling component Triazine Amine component Hue 98 2-Aminonaphthalene- 2-Amino-5-hydroxy- Cyanuric chloride 2-Ethoxyaniline yellowish red 3,6,8-trisulfonic acid naphthalene-7-sulfonic acid 99 " " " p-Aminobenzenesulfonamide " 100 " " " m-Aminobenzenesulfonamide " 101 " " " o-Aminobenzenecarboxamide " 102 " " " p-Aminobenzenecarboxamide " 103 " " " 1-Aminonaphthalene " 104 " " " 2-Aminonaphthalene " 105 " " " 1-N-Ethylaminonaphthalene " 106 " 2-N-Methylamino-5-hydroxy- " p-Aminobenzenesulfonamide " naphthalene-7-sulfonic acid 107 " " " 2-Methoxycarbonylaniline " 108 " " " 2,5-Dimethylaniline " 109 " " " 2-Chloroaniline " 110 " " " o-Toluidine "

Claims (4)

  1. CLAIMS 1. A reactive dye which in the form of the free acid have the general formula I
    where X is chlorine or bromine, R1 is hydrogen or C1-C4-alkyl, R2 is hydrogeri or unsubstituted or substituted C-C4-alkyl, and R3 is phenyl which is unsubstituted or is mono-substituted or polysubstituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxyl, cyano, amino, dimethylamino, diethylamino, C1-C4 alkoxycarbonyl, carbamyl which is unsubstituted or N-monosubstituted or N,N-disubstituted by C1-C4 alkyl, sulfamyl which is unsubstituted or N-monosubstituted or N,N-disubstituted by C1-C4-alkyl, or hydroxysulfonyl, or R3 is naphthyl which is unsubstituted or is monosubstituted or polysubstituted by hydroxysulfonyl, with the proviso that if R2 is unsubstituted C1-C4-alkyl, any phenyl radical R3 is substituted.
  2. 2. A dye as claimed in claim 1, of the formula
    where B is phenyl which is unsubstituted or substituted by methyl, methpxy, chlorine, carboxyl or hydroxysulfonyl, or is sulfonaphthyl, and R4 is hydrogen or methyl.
  3. 3. A dye as claimed in claim 1 and identified in any of the foregoing Examples
  4. 4. A process for dyeing a polyarnide, leather or a cellulosic textile wherein a dye as claimed in any of claims 1 to 3 is used.
GB7937989A 1978-11-04 1979-11-02 Reactive dyes Expired GB2036778B (en)

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DE2847916A DE2847916C2 (en) 1978-11-04 1978-11-04 Reactive dyes and their use

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GB2036778A true GB2036778A (en) 1980-07-02
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JP (1) JPS5565259A (en)
CH (1) CH641486A5 (en)
DE (1) DE2847916C2 (en)
FR (1) FR2440385B1 (en)
GB (1) GB2036778B (en)
IT (1) IT1124857B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284554A (en) 1977-12-23 1981-08-18 Sandoz Ltd. Monoazo compounds having a 6-(2'-N-alkylanilino--4-chloro-1',3',5'-triazinyl-6'-amino or alkylamino)-1-hydroxy-3-sulfonaphthalene coupling component radical

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH655735A5 (en) * 1982-09-17 1986-05-15 Sandoz Ag REACTIVE MONOAZO CONNECTIONS.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB908194A (en) * 1960-08-03 1962-10-17 Ici Ltd New triazine monoazo dyestuffs
JPS49104923A (en) * 1973-02-05 1974-10-04
CH629839A5 (en) * 1976-07-12 1982-05-14 Ciba Geigy Ag Process for preparing fibre-reactive azo dyes
DE2711150A1 (en) * 1977-03-15 1978-09-28 Bayer Ag METHOD OF PREPARING AZOREACTIVE DYES
LU78485A1 (en) * 1977-11-10 1979-06-13 Ciba Geigy Ag REACTIVE COLORS, THEIR PRODUCTION AND USE
CH641197A5 (en) * 1977-12-23 1984-02-15 Sandoz Ag REACTIVE MONOAZO DYES AND METHOD FOR THE PRODUCTION THEREOF.
DE2838271A1 (en) * 1978-09-01 1980-03-13 Bayer Ag AZOREACTIVE DYES
DE2838608A1 (en) * 1978-09-05 1980-03-20 Bayer Ag AZO REACTIVE DYES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284554A (en) 1977-12-23 1981-08-18 Sandoz Ltd. Monoazo compounds having a 6-(2'-N-alkylanilino--4-chloro-1',3',5'-triazinyl-6'-amino or alkylamino)-1-hydroxy-3-sulfonaphthalene coupling component radical

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FR2440385A1 (en) 1980-05-30
CH641486A5 (en) 1984-02-29
JPS5565259A (en) 1980-05-16
DE2847916C2 (en) 1984-04-26
FR2440385B1 (en) 1985-08-23
JPS6329709B2 (en) 1988-06-15
IT7926943A0 (en) 1979-10-30
DE2847916A1 (en) 1980-05-22
GB2036778B (en) 1983-08-17
IT1124857B (en) 1986-05-14

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