GB2036780A - Disazo dyestuffs - Google Patents
Disazo dyestuffs Download PDFInfo
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- GB2036780A GB2036780A GB7940712A GB7940712A GB2036780A GB 2036780 A GB2036780 A GB 2036780A GB 7940712 A GB7940712 A GB 7940712A GB 7940712 A GB7940712 A GB 7940712A GB 2036780 A GB2036780 A GB 2036780A
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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
- C09B62/09—Disazo or polyazo dyes
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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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
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Abstract
Dyestuffs of the formula <IMAGE> in which R1 is H, halogen, alkoxy or acylamino, R2 and R3 are independently H, halogen, alkyl, alkoxy, or acylamino, R4 is halogen, OR5, SR5 or NR6R7 wherein R5 is H, C1-C6-alkyl, aryl, heteroaryl, aralkyl, or cycloalkyl, and R6 and R7 are independently H, amino, optionally substituted C1-C6 alkyl, aryl, heteroaryl, aralkyl or cycloalkyl, or together may complete a 5-or 6- membered hetero ring optionally containing further hetero atoms, and wherein rings A and B may be optionally substituted and their use for the dyeing of cellulose containing materials in bright yellow shades.
Description
SPECIFICATION
Disazo dyestuffs
The invention relates to new yellow disazo dyestuffs of the general formula I
in which R, denotes hydrogen, halogen, alkoxy or acylamino,
R2 and R3 independently of one another denote hydrogen, halogen, alkyl, alkoxy or acylamino and
R4 denotes halogen, OR5, SR5 or NR6R,, wherein
R5 denotes hydrogen, low-molecular alkyl, aryl, hetaryl, aralkyl or cycloalkyl and Re and R, independently of one another denote hydrogen, amino, low-molecular alkyl, aryl, hetaryl,
aralkyl or cycloalkyl, or together form a 5-membered or 6-membered ring, optionally with the
inclusion of one or more hetero-atoms, in particular oxygen and/or nitrogen, it being possible for
alkyl, aryl, hetaryl and aralkyl to be in turn substituted, and in which
the rings A and B can optionally be substituted, and to a process for their preparation, characterised in that one mol of a cyanuric trihalide, one mol of an aminoazo compound of the general formula II
in which
R1, R2 and R3 have the abovementioned meaning one mol of an aminoazo compound of the general formula III
in which
the rings A and B can optionally be substituted, and optionally one mol of a compound of the general formula IV
HR4 IV in which
R4 is other than halogen, are reacted with one another in any desired sequence in the presence of an acid-binding agent, the aminoazo compounds of the general formulae II and Ill being prepared in a known manner.
Advantageous dyestuffs are those of the general formula V
in which
R1, R2, R3 and R4 have the abovementioned meaning and o,p,q,r and s are 0 or 1, but
o + p + q + r + s equals 2, and in which
the rings A and B can optionally be substituted.
Particularly advantageous dyestuffs are those of the general formulae I and V in which R4, o, p, q, rand s have the abovementioned meaning and
R, denotes NHCOCH3 or NHCONH2 when
R2 and R3 represent H, or
R2 denotes H, CH3, OCH3 or OC2H5 wheri- R1 and R3 represent H, and in which
the rings A and B can optionally be substituted.
Very particularly advantageous dyestuffs are those of the general formulae I and V in which
R1, R2, R3, o, p, q, r and s have the abovementioned meaning,
R4 denotes OH, OCH3, OC2H4OCH3, NH2, NHC2H4OH, N(C2H4OH)2, NC2H4OC2H4, NHC6H5,
N(CH3)C6H5, NH(3-C6H4SO3H) or NH(4-C6H4SO3H), N(CH3)C2H4OH, N(C2H5)C2H4OH, NHCH2CH(CH3)OH or N(CH2CH(CH3)OH)2 and
the rings A and B can optionally be substituted.
Interesting dyestuffs are those of the general formulae I and V in which
R1, R2, R3, o, p, q, r and s have the abovementioned meaning,
R4 denotes NH2, NHC2H4OH, N(C2H4OH)2 or N(CH3)C2H4OH and
the rings A and B can optionally be substituted.
Dyestuffs of the general formulae I and B which are prepared using compounds of the general formula VI
in which
R8 and R9 independently of one another denote H, Cl, OH, OCH3, OC2H5, OCOCH3, OCOC@H5, OSO2CH3, OSO2C6H5, CH3, CH2SO3H, NH2, NHCOCH3, NHCOCH2OH, NHCOC6H5, NHCONH2,
NHSO2CH3, NHSO2C6H5, COOH or SO3H, and in which
the ring B can optionally be substituted, as compounds of the general formula lil are preferred.
Dyestuffs of the general formulae I and V which are prepared using compounds of the general formula VII
in which
R10 denotes H, CH3, CI, OCH3, OC2H5 or SO3H and Rt, denotes H, CH3, Cl, OCH3, OC2H5, NHCOCH3 or NHCONH2, and in which
the ring B can optionally be substituted, as compounds of the general formula III are particularly preferred.
Dyestuffs of the general formulae I and V which are prepared using compounds of the general formula VIII
in which R.2 denotes H, Cl, CH3, OCH3, OC2H5 or OH and
S, and S2 independently of one another denote H, SO3H, COOH orCH2SO3H, and in which the ring A can optionally be substituted, as compounds of the general formula Ill are very particularly preferred.
Particularly interesting dyestuffs are those of the general formulae I and V which are prepared using compounds of the general formula VIII in which
R12 denotes 4-H, 4-CH3, 4-OH or 4-OCH3, when
S1 represents 3-SO3H, 3-COOH or 3-CH2SO3H and S2 represents H, or
R12 denotes 3-H, when S1 represents 4-SO3H, 4-OOOH or 4-OH2SO3H and S2 represents H, and in which
the ring A can optionally be substituted, as compounds of the general formula Ill.
Dyestuffs of the general formula IX
in which
o,p,q,r and s are 0 or 1, but o + p + q + r + s equals 2, and in which
R1 denotes NHCQCH3 or NHCONH2, when
R2 and R3 represent H, or
R2 denotes H, OCH3 or OC2H5, when
R1 and R3 represent H, and
R4 denotes NH2, NHC2H4OH, N(C2H40H)2 or N(CH3)C 2H40H, R10 denotes H, CH3, Cl, OCH3, OC2Hs or SO3H, R11 denotes H, CH3, Cl, OCH3, OC2H5, NHCOCH3 or NHCONH2 and
R12 denotes 4-H, 4-OH3, 4-OH or 4-OCH3, when
S represents 3-SO3H, 3-OOOH or 3-OH2SO3H, or
R12 denotes 3-H, when
S represents 4-SO3H, 4-OOOH or 4-OH2SO3H, are of very particular interest.
Examples of aminoazo compounds of the general formula II are those which are obtained by
diazotising 2-aminonaphthalenedisulphonic acids, such as, for example, 2-aminonaphthalene-1 5
disulphonic acid, 2-aminonaphthalene-3,6-disulphonic acid, 2-Aminonaphthalene-3,7-disulphonic acid,
2-aminonaphthalene-4,8-disulphonic acid, 2-aminonaphthalene-5,7-disulfonic acid or 2aminonaphthalene-6,8-disulphonic acid, and coupling the diazotisation products to aminobenzenes which are optionally substituted in the 2-position or in the 3-position, such as, for example, aniline, 2
methylaniline, 2-methoxyaniline, 2-ethoxyaniline, 2-chloroaniline, 3-acetylaniline or 3aminophenylurea; the #-methanesulphonic acids of the abovementioned aminobenzenes can equally well be used as coupling components, the protective group being split off again, by treatment with acids
or alkalis, after the coupling.
Examples of aminoazo compounds of the general formula III are those which are obtained by diazotising optionally substituted aminobenzenes, such as, for example, aniline, 2-chloroaniline, 3chloroaniline, 4-chloroaniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 2-methoxyaniline, 3
methoxyaniline, 4-methoxyaniline, 2-ethoxyaniline, 3-ethoxyaniline, 4-ethoxyaniline, 2aminobenzenesulphonic acid, 3-aminobenzenesulphonic acid, 4-aminobenzenesulphonic acid, anthranilic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 5-amino-2-hydroxybenzoic acid, 5amino 2-methylbenzenesulphonic acid, 3-aminophenylmethanesulphonic acid or 4aminophenylmethanesulphonic acid, and coupling the diazotisation products to optionally substituted aminobenzenes, such as, for example, aniline, 2-methylaniline, 3-methylaniline, 2-methoxyaniline, 3 methoxyaniline, 2-ethoxyaniline, 3-ethoxyaniline, 2-methoxy-5-methylaniline, 2-ethoxy-5
methylaniline, 5-methoxy-2-methylaniline, 2-aminophenol, 3-aminophenol, 2,5-dimethylaniline, 3,5dimethylaniline, 2,5-dimethoxyaniline, 3-acetylaminoaniline, 3-methylsulphonylaminoaniline, 3aminophenylurea, 1,3-diaminobenzene, 3-amino-4-methylbenzenesulphonic acid, 3-amino-4hydroxybenzenesulphonic acid, 3-amino-4-methoxybenzenesulphonic acid or 3 aminophenylmethanesulphonic acid; the w-methanesulphonic acids of the abovementioned aminobenzenes can equally well be used as coupling components, the protective group being split off again, by treatment with acids or alkalis, after the coupling.
Examples of aminoazo compounds of the general formula Ill are also those which are obtained by diazotising optionally further substituted 4-nitroaminobenzenes, such as, for example, 4-nitroaniline, 4- nitro-2-methoxyaniline, 4-nitroaniline-2-sulphonic acid or 4-nitro-5-methoxyaniline-2-sulphonic acid, and coupling the diazotisation products to optionally substituted hydroxybenzenes, such as, for example, phenol, salicylic acid, 3-hydroxybenzoic acid, 2-hydroxy-6-methylbenzoic acid, 2hydroxybenzenesulphonic acid or 3-hydroxybenzenesulphonic acid, and then reducing the nitroazo compound to give the aminoazo compound.
Examples of aminoazo compounds of the general formula Ill are also those which are obtained on treating other aminoazo compounds of the general formula Ill with agents with which sulphonic acid radicals can be introduced, such as, for example, sulphuric acid, oleum or sulphur trioxide, an example being 4-amino-3,4'-azobenzenedisulphonic acid.
Examples of compounds of the general formula IV are water, methanol, ethanol, glycol, 2methoxyethanol, phenol, thiophenol, ammonia, hydrazine, methylamine, ethylamine, dimethylamine, diethylamine, ethanolamine, diethanolamine, N-methylethanolamine, N-ethylethanolamine, glycine, Nmethylglycine, taurine, N-methyltaurine, aminomethanesulphonic acid, Nmethylaminomethanesulphonic acid, aniline, N-methylaniline, 3-aminobenzenesulphonic acid, 4- aminobenzenesulphonic acid, 2-aminonaphthalene-4,8-disulphonic acid, 2-aminopyridine, 2aminothiazole, benzylamine, pyrrolidine, piperidine, morpholine, 1 -amino-2-propanol and bis-(2hydroxypropyl)-amine.
The reaction between the cyanuric halide, for example cyanuric fluoride, cyanuric chloride or cyanuric bromide, the aminoazo compounds of the general formulae II and Ill and the compounds of the general formula IV is carried out in three stages in any desired sequence, the first stage being carried out at about 0--100, the second at about 3550 and the third at about 80-11000, and the acid thereby formed being neutralised with alkaline agents, such as, for example, sodium acetate, sodium bicarbonate, sodium carbonate, sodium hydroxide solution, lithium carbonate, lithium hydroxide, potassium carbonate or potassium hydroxide.
Those aminoazo compounds or compounds of the general formula IV which carry groups conferring solubility in water are advantageously reacted first.
The dyestuffs are precipitated from the solution by adding salt and are isolated and dried or isolated by spray-drying. In general, they are obtained in the form of salts, in particular the alkali metal salts, and preferably the sodium salts. The formulae given are those of the free acids.
The new dyestuffs dye cellulose-containing materials in clear yellow colour shades.
In the examples which follow, "parts" denote parts by weight, "percentages" denote percentages by weight and the temperature is given in degrees Centigrade.
EXAMPLE 1
29.5 parts of the aminoazo compound, of the general formula II, obtained from 2 aminonaphthalene-4,8-disulphonic acid and aniline are dissolved in 1,000 parts of water, and a solution of 13.5 parts of cyanuric chloride in 100 parts of acetone is added at 00, the hydrochloric acid liberated being neutralised by adding 46.5 parts of an aqueous 20% strength solution of sodium carbonate,
When the first reaction stage has ended, 22.2 parts of the aminoazo compound, of the general formula
Ill, obtained from 3-aminobenzenesulphonic acid and 2-methoxyaniline are dissolved in 1,000 parts of water and the solution is added to the first mixture. The temperature is increased to 400 and the hydrochloric acid liberated is neutralised by adding 46.5 parts of 20% strength sodium carbonate solution.When the second reaction stage has ended, 15.2 parts of diethanolamine are added. The temperature is increased to 900, and the mixture is then stirred at this temperature for a further 3 hours.
The dyestuff is precipitated by adding 450 parts of potassium chloride and is isolated. After drying, an orange-coloured powder, an aqueous solution of which dyes cellulose-containing materials in greenishtinged yellow shades, is obtained.
EXAMPLES 2 to 4
Very similar dyestuffs are obtained if, instead of the diethanolamine used in Example 1, 1 8 parts of an aqueous 25% strength solution of ammonia or 8.9 parts of ethanolamine or N-methylethanolamine are used.
EXAMPLE 5
18.6 parts of the aminoazo compound, of the general formula Ill, which is obtained bydiazotising 4-nitroaniline, coupling the diazotisation product to salicylic acid and then reducing the coupling product are dissolved in 1,000 parts of water and the solution is reacted with a suspension of 1 3.5 parts of cyanuric chloride in 100 parts of water at 00, the hydrochloric acid liberated being neutralised by adding 46.5 parts of an aqueous 20% strength solution of sodium carbonate.When the first reaction stage has ended, 29.5 parts of the aminoazo compound, of the general formula II, which is obtained
Compound of the general formula III, Compound of the Example obtained from general formula IV 66 4-aminophenylmethanesulphonic acid and ammonia 3-acetylaminoaniline 67 3-aminophenyl methanesul phonic acid and diethanolamine 3-acetylaminoaniline 68 .. ethanolamine 69 .. ammonia 70 4-aminobenzenesul phonic acid and diethanolami ne 3-aminophenylurea 71 1, ethanolamine 72 .. ammonia 73 3-am i nobenzenesu I phonic acid and diethanolamine 3-aminophenylurea 74 " ethanolamine 75 " ammonia 76 4-aminobenzoic acid and 3-aminophenylurea diethanolamine 77 .. ethanolamine 78 " ammonia 79 3-aminobenzoic acid and 3-aminophenylurea diethanolamine 80 It ethanolamine 81 " ammonia 82 5-amino-2-methylbenzenesulphonic acid and diethanolamine 3-aminophenylurea 83 .. ethanolamine 84 " ammonia 85 4-aminophenylmethanesulphonic acid and diethanolamine 3-aminophenylurea 86 " ethanolamine 87 " ammonia 88 3-aminophenylmethanesu Iphonic acid and diethanolamine 3-aminophenylurea 89 .. ethanolamine 90 .. ammonia 91 4-nitroaniline and salicylic acid diethanolamine 92 " ethanolamine 93 " ammonia
Compound of the general formula III, Compound of the Example obtained from general formula IV 38 3-aminobenzolc acid and 2-methoxyaniline ethanolamine 39 " ammonia 40 5-amino-2-methylbenzenesulphonic acid and diethanolamine 2-methoxyaniline 41 .. ethanolamine 42 1, ammonia 43 4-aminophenylmethanesulphonic acid and diethanolamine 2-methoxyaniline 44 " ethanolamine 45 " ammonia 46 3-aminophenylmethanesulphonic acid and diethanolamine 2-methoxyaniline 47 ,, ethanolamine 48 " ammonia 49 4-aminobenzenesulphonic acid and diethanolamine 3-acetylaminoanil ine 50 .. ethanolamine 51 1, ammonia 52 3-aminobenzenesulphonic acid and diethanolamine 3-acetylaminoaniline 53 .. ethanolamine 54 1, ammonia 55 4-aminobenzoic acid and 3-acetylaminoaniline diethanolamine 56 .. ethanolamine 57 ,, ammonia 58 3-aminobenzoic acid and 3-acetylaminoaniline diethanolamine 59 " ethanolamine 60 55 ammonia 61 5-amino-2-methylbenzenesulphonic acid and diethanolamine 3-acetylaminoaniline 62 55 ethanolamine 63 .. ammonia 64 4-aminophenylmethanesulphonic acid and diethanolamine 3-acetylaminoaniline 65 " ethanolamine
Compound of the general formula III, Compound of the Example obtained from general formula IV 7 4-aminobenzenesulphonic acid and aniline diethanolamine 8 " ethanolamine 9 .. ammonia 10 3-am inobenzeneaul phon i c acid and aniline diethanol gamine 11 .. ethanolamine 12 .. ammonia 13 4-aminobenzoic acid and aniline diethanolamine 14 .. ethanolamine 15 " ammonia 16 3-aminobenzoic acid and aniline diethanolamine 17 1, ethanolamine 18 " ammonia 19 5-amino-2-methylbenzenesulphonic acid and aniline diethanolamine 20 " ethanolamine 21 .. ammonia 22 4-aminopheny I methanesu Iphonic acid and aniline diethanolamine 23 .. ethanolamine 24 55 ammonia 25 3-aminophenylmethanesulphonic acid and aniline diethanolamine 26 " ethanolamine 27 " ammonia 28 4-aminobenzenesulphonic acid and 2-methoxyaniline diethanolamine 29 .. ethanolamine 30 " ammonia 31 3-aminobenzenesulphonic acid and 2-methoxyaniline diethanolamine 32 " ethanolamine 33 " ammonia 34 4-aminobenzoic acid and 2-methoxyaniline diethanolamine 35 " ethanolamine 36 55 ammonia 37 3-aminobenzoic acid and 2-methoxyaniline diethanolamine from 2-aminonaphthalene-4,8-disulphonic acid and aniline are dissolved in 1,000 parts of water and the solution is added to the first mixture.The temperature is increased to 400 and the subsequent procedure is as in Example 1. An orange-coloured powder, an aqueous solution of which dyes cellulosecontaining materials in greenish-tinged yellow shades, is obtained.
EXAMPLE 6
Very similar dyestuffs are obtained if, instead of the diethanolamine used in Example 5, 18 parts of an aqueous 25% strength solution of ammonia, 8.9 parts of ethanolamine or 10.9 parts of Nmethylethanolamine are used.
EXAMPLES 7 to 96
If the procedure of the processes indicated in Examples 1-6 is followed and the product obtained from 2-aminonaphthalene-4,8-disulphonic acid and aniline is used as the compound of the general formula II and the compounds indicated in the table below are used as the compounds of the general formulae Ill and IV, yellow dyestuffs for cellulose-containing materials are likewise obtained::
Compound of the general formula Ill, Compound of the Example obtained from general formula IV 94 4-aminoazobenzene and 2 mols of S03 diethanolamine (4-ami noazobenzene-2,4 '-di su I phoni c acid) 95 .. ethanolamine 98 It ammonia Similarly good dyestuffs are obtained using N-methylethanolamine as compound IV.
Similarly good dyestuffs are obtained if, instead of the compound of the general formula II used in
Examples 1-96, those obtained from 2-aminonaphthalene-4,8-disulphonic acid and 2-methoxyaniline or 3-acetaminoaniline and 3-aminophenylurea are used.
Claims (15)
1. A dyestuff of the general formula
in which
R, denotes a hydrogen or halogen atom or an alkoxy or acylamino group,
R2 and R3 independently of each other denote a hydrogen or halogen atom or an alkyl, alkoxy, or
acylamino group and
R4 denotes a halogen atom or an OR5, SR5 or NR6R7 group in which Rs denotes a hydrogen atom, C1 to C6 alkyl, aryl, hetaryl, aralkyl or cycloalkyl and R6 and R7 independently of each other denote a hydrogen atom or an amino, C, to C6a alkyl, aryl, hetaryl, aralkyl or cycloalkyl group, or together form a 5-membered or 6-membered ring,
optionally with the inclusion of one or more hetero-atoms, and the alkyl, aryl, hetaryl and aralkyl
groups are optionally substituted, and in which
the rings A and B are optionally substituted.
2. A dyestuff according to claim 1 in which R6 and R7 together form a 5-membered or 6membered ring with the inclusion of one or more oxygen and/or nitrogen atoms.
3. A dyestuff according to claim of the general formula
in which R1,R2, R3 and R4 have the same meanings as in claim 1 and
o,p,q,r and s are 0 or 1, but o + p + q + r + s equals 2, and in which
the rings A and B are optionally substituted.
4. A dyestuff according to any of the foregoing claims in which R4 has the same meaning as in claim, o, q, r rand s have the same meaning as in claim 3 and
R, denotes NHCOCH3 or NHCONH2 when
R2 and R3 denote hydrogen atoms, or
R2 denotes a hydrogen atom or a methyl, methoxy, or ethoxy group when
R1 and R3 denote hydrogen atoms, and in which
the rings A and B are optionally substituted.
5. A dyestuff according to any of the foregoing claims in which R1, R2 and R3 have the same meanings as in claim 1 or 4,
op, q, rand s have the same meaning as in claim 3 and
R4 denotes OH, OCH3, OC2H4OCH3, NH2, NHC2H4OH, N(C2H4OH)2, N(CH3)C2H4OH, N(C2H5)C2H4OH, NHCH2CH(CH3)OH, N(CH2CH(CH3)OH2, NC2H4OC2H4-, NHC6H5, N(CH3)C6H5, NH(3-C6H4SO3H)
or NH(4-C6H4SO3H) and in which
the rings A and B are optionally substituted.
6. A dyestuff according to claim 5, in which
R1, R2 and R3 have the same meaning as in claim 1 or 4,
o, p, q, rand shave the same meaning as in claim 3, and
R4 denotes NH2, NHC2H4OH, N(C2H4OH)2 or N(CH3)C2H4OH, and in which
the rings A and B are optionally substituted.
7. A dyestuff according to any of the foregoing claims in which the moiety consisting of rings A and B and the invervening azo bridge is a radical of the general formula
in which
R8 ano R9 independently of each other denote a hydrogen or chlorine atom or an OH, OCH3, OC2H5,
OCOCH3, OCOC6H5, OSO2CH3, OSO2C6H5, CH3, CH2SO3H, NH2, NHCOCH3, NHCOCH2OH, NHCOC6H5, NHCONH2, NHSO2CH3, NHSO2C6H5 COOH or SO3H group, and in which
the ring B is optionally substituted.
8. A dyestuff according to claim 7 in which the radical (Va) is of the general formula
in which
Rio denotes H, CH3, Cl, OCH3, OC2H5 or SO3H and
R1, denotes H, CH3, Cl, OCH3, OC2H5, NHCOCH3 or NHCONH2, and in which
the ring B is optionally substituted.
9. A dyestuff according to any of the foregoing claims in which the moiety consisting of rings A and B and the intervening azo bridge is a radical of the general formula
in which R.2 denotes a hydrogen or chlorine atom or a methyl, methoxy, ethoxy or hydroxyl group
S1 and S2 independently of each other denote a hydrogen atom or a SO3H, COOH or CH2SO3H
group, and in which
the ring A is optionally substituted.
10. A dyestuff according to claim 9 in which
R12 denotes 4-H, 4-OH3, 4-OH or 4-OCH3, when
S1 denotes 3-SO3H, 3-COOH or 3-CH2SO3H and S2 denotes a hydrogen atom,
R12 denotes 3-H, when
S, denotes 4-SO3H, 4-OOOH or 4-CH2SO3H and S2 denotes a hydrogen atom.
and in which
the ring A can optionally be substituted.
11. A dyestuff according to claim 1 of the general formula
in which o, p, q, r and s are 0 or 1, but o + p + q + r + s equals 2, and in which
R1, R2 and R3 have the same meanings as in claim 4, R, has the same meaning as in claim 6,
R10 and R11 have the same meanings as in claim 8, and R12 and S have the same meanings as in claim 10.
1 2. A dyestuff according to claim 1 as hereinbefore specifically identified.
13. A process for the production of a dyestuff as claimed in claims in which, per mol a cyanuric trihalide, one mol of an aminoazo compound of the general formula
in which R1,R2 and R3 have the same meanings as in claim 1, one mol of an aminoazo compound of the general formula
in which
the rings A and B are optionally substituted, if R4 is other than a halogen atom, one mol of a compound of the general formula HR4 in which
R4 has the same meaning as in claim 1, other than a halogen atom, are reacted with one another in any desired sequence in the presence of an acid-binding agent.
14. A process for the production of a dyestuff as claimed in claim 1 when carried out substantially as described in any one of the Examples.
15. A dyestuff as claimed in claim 1 when produced by the process of claim 14.
1 6. A process for dyeing a cellulose-containing material comprising treating the material with a dyestuff as claimed in any of claims 1 to 1 2 and 1 5.
1 7. A cellulose-containing material when dyed by the process of claim 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782851787 DE2851787A1 (en) | 1978-11-30 | 1978-11-30 | DISAZO DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2036780A true GB2036780A (en) | 1980-07-02 |
| GB2036780B GB2036780B (en) | 1982-12-01 |
Family
ID=6055940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7940712A Expired GB2036780B (en) | 1978-11-30 | 1979-11-26 | Disazo dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5578059A (en) |
| BR (1) | BR7907757A (en) |
| DE (1) | DE2851787A1 (en) |
| FR (1) | FR2442873B1 (en) |
| GB (1) | GB2036780B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4997919A (en) * | 1988-06-21 | 1991-03-05 | Ciba-Geigy Corporation | Azo direct dyes containing a non-reactive triazinyl moiety |
| EP0465420A1 (en) * | 1990-07-02 | 1992-01-08 | Ciba-Geigy Ag | Azo dyestuffs |
| US5519121A (en) * | 1994-03-03 | 1996-05-21 | Bayer Aktiengesellschaft | Triazinyl-amino bridge-containing disazo dyestuffs |
| EP0714955A1 (en) * | 1994-12-02 | 1996-06-05 | Ciba-Geigy Ag | Azodyestuffs, process for their preparation and the use thereof |
| WO2002092698A1 (en) * | 2001-05-11 | 2002-11-21 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| WO2004007618A1 (en) * | 2002-07-16 | 2004-01-22 | Avecia Limited | Disazo dyes and ink jet inks containing them |
| WO2009013459A1 (en) * | 2007-07-25 | 2009-01-29 | Fujifilim Imaging Colorants Limited | Compound, ink, process and use |
| US20110216117A1 (en) * | 2008-06-19 | 2011-09-08 | Nippon Kayaku Kabushiki Kaisha | Water-soluble azo compound or salt thereof, ink composition, and colored matter |
| WO2012072210A1 (en) | 2010-11-29 | 2012-06-07 | Dystar Colours Distribution Gmbh | Metal free acid dyes, methods for the production thereof and their use |
| EP2740769A1 (en) | 2012-12-10 | 2014-06-11 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for the production thereof and their use |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2752115B1 (en) * | 1996-07-31 | 1999-01-29 | Inside Technologies | PROGRAMMABLE SWITCH, ADJUSTABLE CAPACITY AND RESONANT CIRCUIT MADE BY SUCH A SWITCH |
| JP2007307032A (en) * | 2006-05-17 | 2007-11-29 | Matsushita Electric Ind Co Ltd | Iron |
| TW201022368A (en) * | 2008-09-30 | 2010-06-16 | Nippon Kayaku Kk | Water soluble azo compound or its salt, ink composition and coloured article |
| JPWO2011068046A1 (en) * | 2009-12-02 | 2013-04-18 | 日本化薬株式会社 | Water-soluble azo compound or salt thereof, ink composition and colored body |
-
1978
- 1978-11-30 DE DE19782851787 patent/DE2851787A1/en not_active Withdrawn
-
1979
- 1979-11-26 GB GB7940712A patent/GB2036780B/en not_active Expired
- 1979-11-29 FR FR7929408A patent/FR2442873B1/en not_active Expired
- 1979-11-29 BR BR7907757A patent/BR7907757A/en unknown
- 1979-11-29 JP JP15495579A patent/JPS5578059A/en active Granted
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4997919A (en) * | 1988-06-21 | 1991-03-05 | Ciba-Geigy Corporation | Azo direct dyes containing a non-reactive triazinyl moiety |
| EP0465420A1 (en) * | 1990-07-02 | 1992-01-08 | Ciba-Geigy Ag | Azo dyestuffs |
| US5328995A (en) * | 1990-07-02 | 1994-07-12 | Ciba-Geigy Corporation | Azo dyes containing triazine middle components and a 1,4-phenylene-2,5-disubstituted coupling component |
| EP0719838A1 (en) * | 1990-07-02 | 1996-07-03 | Ciba-Geigy Ag | Azo dyestuffs |
| US5519121A (en) * | 1994-03-03 | 1996-05-21 | Bayer Aktiengesellschaft | Triazinyl-amino bridge-containing disazo dyestuffs |
| EP0714955A1 (en) * | 1994-12-02 | 1996-06-05 | Ciba-Geigy Ag | Azodyestuffs, process for their preparation and the use thereof |
| US5644040A (en) * | 1994-12-02 | 1997-07-01 | Ciba-Geigy Corporation | Azo dyes having two monoazo-chromophores bound to a halotriazinyl radical processes for their preparation and their use |
| US7029503B2 (en) | 2001-05-11 | 2006-04-18 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and method of dyeing cellulose or cellulose-containing fibers |
| WO2002092698A1 (en) * | 2001-05-11 | 2002-11-21 | Nippon Kayaku Kabushiki Kaisha | Disazo compound, reactive dye composition, and methods of dyeing cellulose or cellulose-containing fiber |
| WO2004007618A1 (en) * | 2002-07-16 | 2004-01-22 | Avecia Limited | Disazo dyes and ink jet inks containing them |
| WO2004007619A1 (en) * | 2002-07-16 | 2004-01-22 | Avecia Limited | Disazo dyes and ink jet inks containing them |
| GB2405150A (en) * | 2002-07-16 | 2005-02-23 | Avecia Ltd | Disazo dyes and ink jet inks containing them |
| GB2405150B (en) * | 2002-07-16 | 2005-10-19 | Avecia Ltd | Disazo dyes and ink jet inks containing them |
| US7150783B2 (en) | 2002-07-16 | 2006-12-19 | Fujifilm Imaging Colorants Limited | Disazo dyes and ink jet inks containing them |
| US7163576B2 (en) | 2002-07-16 | 2007-01-16 | Fujifilm Imaging Colorants Limited | Disazo dyes and ink jet inks containing them |
| GB2462403A (en) * | 2007-07-25 | 2010-02-10 | Fujifilm Imaging Colorants Ltd | Compound, ink, process and use |
| WO2009013459A1 (en) * | 2007-07-25 | 2009-01-29 | Fujifilim Imaging Colorants Limited | Compound, ink, process and use |
| US7927411B2 (en) | 2007-07-25 | 2011-04-19 | Fujifilm Imaging Colorants Limited | Compound, ink, process and use |
| GB2462403B (en) * | 2007-07-25 | 2012-08-08 | Fujifilm Imaging Colorants Ltd | Ink containing 1,3,5 - triazine compound |
| US20110216117A1 (en) * | 2008-06-19 | 2011-09-08 | Nippon Kayaku Kabushiki Kaisha | Water-soluble azo compound or salt thereof, ink composition, and colored matter |
| WO2012072210A1 (en) | 2010-11-29 | 2012-06-07 | Dystar Colours Distribution Gmbh | Metal free acid dyes, methods for the production thereof and their use |
| US8979947B2 (en) | 2010-11-29 | 2015-03-17 | Dystar Colours Distribution Gmbh | Metal free acid dyes, methods for the production thereof and their use |
| EP2740769A1 (en) | 2012-12-10 | 2014-06-11 | DyStar Colours Distribution GmbH | Metal free acid dyes, process for the production thereof and their use |
| US9714347B2 (en) | 2012-12-10 | 2017-07-25 | Dystar Colours Distribution Gmbh | Metal free acid dyes, process for the production thereof and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2851787A1 (en) | 1980-06-12 |
| FR2442873A1 (en) | 1980-06-27 |
| JPS5578059A (en) | 1980-06-12 |
| FR2442873B1 (en) | 1986-08-22 |
| JPS6252784B2 (en) | 1987-11-06 |
| GB2036780B (en) | 1982-12-01 |
| BR7907757A (en) | 1980-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19961126 |