GB1589927A - Disazo-thiazole dyestuffs - Google Patents

Disazo-thiazole dyestuffs Download PDF

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GB1589927A
GB1589927A GB16167/77A GB1616777A GB1589927A GB 1589927 A GB1589927 A GB 1589927A GB 16167/77 A GB16167/77 A GB 16167/77A GB 1616777 A GB1616777 A GB 1616777A GB 1589927 A GB1589927 A GB 1589927A
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aniline
ethyl
optionally substituted
dyestuff
blue
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Priority to GB16167/77A priority Critical patent/GB1589927A/en
Priority to DE19782816629 priority patent/DE2816629A1/en
Priority to IT22406/78A priority patent/IT1174363B/en
Priority to JP4582078A priority patent/JPS53130729A/en
Priority to FR7811419A priority patent/FR2388025A1/en
Priority to ES468949A priority patent/ES468949A1/en
Publication of GB1589927A publication Critical patent/GB1589927A/en
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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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes

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  • Organic Chemistry (AREA)
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Description

(54) DISAZO-THIAZOLE DYESTUFFS (71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, Imperial Chemical House, Millbank, London SW1P 3JF, a British Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to dyestuffs and more particularly to disazo dyestuffs containing a heterocyclic nucleus.
According to the present invention there are provided disazo dyestuffs, devoid of ionic water-solubilising groups and having the formula:
wherein A represents the residue of a diazo component; E represents the residue of a coupling component; and R represents hydrogen or a substituent. Examples of the substituent R include optionally substituted hydrocarbon radicals, e.g. alkyl, aryl, cycloalkyl or aralkyl radicals, or hydroxy, alkoxy, acyloxy, halogen, acylamido, cyano, alkylthio, aryi-thio, alkoxycarbonyl or aminocarbonyl.
The residue A may be an optionally substituted aryl or heterocyclic radical.
As examples of the optionally substituted aryl radicals represented by A there may be mentioned optionally substituted naphthyl radicals, and preferably optionally substituted phenyl radicals, in particular phenyl radicals containing one or more substituents such as chlorine, bromine, cyano, trifluoromethyl, nitro, alkyl such as methyl, alkoxy such as methoxy and ethoxy, alkyl sulphonyl such as methylsulphonyl, alkyl carbonyl such as acetyl, acylamino such as acetylamino, phthalyl (so as to form an anthraquinone nucleus) alkoxy carbonyl such as methoxycarbonyl and ethoxycarbonyl and hydroxy and alkoxy substituted derivatives thereof such as p-methoxy- ethoxycarbonyl, fi-hydroxyethoxycarbonyl and ss-Gss' ethoxyethoxy) ethoxycarbonyl, aminosulphonyl, and N-alkyl, N::N-di-alkyl and N-phenyl derivatives thereof such as N-methylaminosulphonyl, N,N-diethylaminosulphonyl, N-phenylaminosulphonyl and N-ethyl-N-phenylaminosulphonyl, aminocarbonyl and N-alkyl and N,N-di-alkyl derivatives thereof such as N-methylaminocarbonyl and N,N-diethylaminocarbonyl, and aminosulphonyloxy and N-alkyl and N,N-di-alkyl derivatives thereof.
As examples of the optionally substituted heterocyclic radicals represented by A there may be mentioned: 2-(thienyl) 3-(pyrazolyl) 2- or 5-(imidazolyl) 3-( 1,2,4-triazolyl) S-(1,2,3,4-tetrazolyl) 2-(thiazolyl) 5-(isothiazolyl) 5-(1,2,4-thiadiazolyl) 2-(1,3,4-thiadiazolyl) 3-(pyridyl) 2-(benzoxazolyl) 2-(benzthiazolyl) 3-(benz-2,1-isothiazolyl) 3-(indazolyl) 3-(thienyl-2,3-b-pyridine) 3 -(isothiazolyl-3,4-d-pyrimidine) 3-(isothiazolyl-3,4-b-pyridine) 3-(isothiazolyl-3 ,4-b-thiophene) The residue E may be the residue of a coupling component of the acylacetarylamide, pyrazolone, aminopyrazole, phenol, 2,6-di-hydroxypyridine, naphthol or arylamine series, and is preferably of the formula::
wherein R' and R2 each independently represent a hydrogen atom or an optionally substituted hydrocarbon radical, especially an optionally substituted lower alkyl radical, and the benzene ring B can contain additional substituents or form part of an optionally further substituted naphthalene or quinoline ring.
E especially represents a radical of the formula:
wherein W is hydrogen, lower alkyl or lower alkoxy, V is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, trifluoromethyl, cyano, -SO2T3 or acylamino, in particular au acylamino group of the formula -NHCOT2 or -NHSO2T3, wherein T2 is hydrogen, alkyl especially lower alkyl, aryl or -NHT4, T3 is optionally substituted lower alkyl or aryl, T4 is hydrogen, alkyl or aryl, R3 is hydrogen or an optionally substituted alkyl especially lower alkyl radical, and R4 is hydrogen or an optionally substituted alkyl, especially lower alkyl, or optionally substituted aryl or cycloalkyl.
As examples of the optionally substituted lower alkyl radicals represented by R3 and R4 there may be mentioned hydroxy lower alkyl such as ss-hydroxyethyl, ssor γ-hydroxypropyl and #-hydroxybutyl, lower alkoxy lower alkyl such as ss-(methoxy or ethoxy)ethyl and γ;-methoxypropyl, cyano lower alkyl such as ss-cyanoethyl aryl lower alkyl such as benzyl and ss-phenylethyl, carboxy lower alkyl such as ss-carboxyethyl and #-carboxybutyl lower alkoxy carbonyl lower alkyl such as ss-methoxycarbonylethyl, hydroxy lower alkoxy lower alkyl such as ss-(ss'-hydroxyethoxy)ethyl, lower alkoxy lower alkoxy lower alkyl such as ss-(ss'-methoxyethoxy)ethyl, lower alkoxy lower alkoxy carbonyl lower alkyl such as ss-(ss'-methoxyethoxycarbonyl)ethyl, acyloxy lower alkyl in particular lower alkylcarbonyloxy lower alkyl such as ss-acetoxyethyl and #-acetoxybutyl, chloro lower alkyl such as ss-chloroethyl and γ-chloropropyl, lower alkoxycarbonyloxy lower alkyl such as ss-ethoxycarbonyloxy-ethyl, lower alkylcarbonyl lower alkyl, γ;-chloro-ss-hydroxypropyl, lower alkoxycarbonyl lower alkoxycarbonyl lower alkyl, cyano lower alkoxy lower alkyl, lower alkoxycarbonyl lower alkylthio lower alkyl, lower alkoxy lower alkoxy lower alkoxycarbonyl lower alkyl, cyano alkoxycarbonyl lower alkyl, lower alkylsulphonylamino lower alkyl, lower alkylsulphonyl lower alkyl and hydroxy lower alkoxycarbonyl lower alkyl.
As examples of cycloalkyl radicals represented by R3 and R4 there may be mentioned cyclopentyl and cyclohexyl.
It is preferred that the alkyl and alkoxy radicals listed above are lower alkyl and lower alkoxy radicals.
Throughout this specification the terms "lower alkyl" and "lower alkoxy" are used to denote alkyl and alkoxy radicals respectively containing from 1 to 4 carbon atoms.
According to a further feature of the invention there is provided a process for the manufacture of the disazo dyestuffs as hereinbefore defined which comprises diazotising an amine of the formula -A-NH2, wherein A has the meaning defined above, coupling the resulting diazo compound with an aminothiazole of the formula:
wherein R has the meaning defined above, diazotising the azo intermediate of the formula:
so obtained and coupling the resulting diazo compound with a coupling component of the formula E-H wherein E has the meaning deiined above.
The diazotisation and coupling may be carried out by methods conventionally used for these reactions. For example, the process of the invention may be con ventionally carried out by adding sodium nitrite to a solution or dispersion of the amine A-NH2 in a strong inorganic acid or an aqueous solution thereof, or by stirring the amine with nitrosulsulphuric acid, and adding the resulting solution or dispersion of the diazo component to a solution of the thiazole coupling component in water or in a mixture of water and a water-miscible organic liquid, if necessary adjusting the pH of the mixture to facilitate the coupling reaction, and isolating the resulting azo aminothiazole intermediate by conventional methods.A similar method is then applied to diazotisation of the azo aminothiazole intermediate and subsequent coupling of the diazo compound so obtained with the coupling component E-H.
As examples of the amines of the formula A-NH2 there may be mentioned 1 naphthylamine or 2-chloro-1-naphthylamine, but more especially amines of the benzene series such as aniline, o-, m- or p-toluidine, o-, m- or p-anisidine, o-, m- or p-chloro aniline, o-, m- or p-bromoaniline, o-, m- or p-nitroaniline, 2: 5-dichloroaniline, 2: 4 dinitroaniline, 2: 4-dinitro-6-(chloro or bromo)aniline, 4-methanesulphonylaniline, 4 aminobenzotrifluoride, 4- or 5-nitro-2-toluidine, 4- or 5-nitro-2-anisidine, 4- or 5 chloro-2-anisidine, 4- or 5-chloro-2-toluidine, 4- or 5-bromo-2-anisidine, 2:6-di(chloro or bromo-)A-nitroaniline, 2 :4: 6-trinitroaniline, 2: 4-dinitro-6-carbomethoxyaniline, 2-amino-5-nitrobenzotrifluoride, 2 : 4-bis(methanesulphonyl)aniline, 2-(chloro- or bromo-)-4-nitroaniline, methylanthranilate, 4- or 5-nitromethylanthranilate, 4-amino benzamide, 2 : 6-di(chloro- or bromo-)-aniline-4-sulphonamide, 2: 6di(chloro- or bromo-)-4-methylsulphonylaniline, 2: 5-di(chloro- or bromo-)-4: 6-di-nitroaniline, 2 amino-3: 5-dinitrobenzotrifluoride, 3-amino-2-(chloro- or bromo-)-4: 6-dinitro-(toluene or anisole), 3-aminoAKchloro- or bromo-)-2:6-dinitro-(toluene or anisole), 2- or 4 cyanoaniline, 4-nitro-2-cyanoaniline, 2: 4-dinitro-6-cyanoaniline, 2-nitro-4-cyanoaniline, 2-chloro-4-cyanoaniline, 4-aminodiphenyl, 1- or 2-aminoanthraquinone, 3-amino 2:4:6-trinitrotoluene, 2-(chloro- or bromo-)-4-methylsulphonylaniline, 3-(chloro- or bromo-)-4-thiocyanatoaniline, 2-(chloro- or bromo-)-4-sulphamylaniline, 2-amino-5 nitrophenylmethanesulphone, 2-amino-3:5-dinitrophenylmethylsulphone, 2-amino-3 (chloro- or bromo-)-5-nitrophenylmethylsulphone, 2-sulphamyl-4-nitroaniline, 2 methylsulphamyl-4-nitroaniline, 2-ethylsulphamyl-4-nitroaniline, 2-butylsulphamyl-4nitroaniline, 2-dimethylsulphamyl-4-nitroaniline, 2-methylsulphamyl-4: :6-dinitroaniline, 2-methylsulphamyl-4-nitro-6-(chloro- or bromo-)aniline, 2-phenylsulphamyl-4-nitro aniline, methyl 2-amino-3-(chloro- or bromo-)-5-nitrobenzoate, dimethyl 2-amino terephthalate, dimethyl 2-amino-5-nitroterephthalate, uB-methoxyethyl 4-aminobenzoate, fl-hydroxyethyl 4-aminobenzoate, aniline 2-, 3- or 4-sulphamate, 2-amino-4-chloro phenyl sulphamate and aniline 2-, 3- or 4-N: N-dimethylsulphamate.
As examples of the 2-aminotbiazoles of formula
which may be used as middle components there may be mentioned: 2-aminothiazole, 2-amino-4-methylthiazole, 2-amino-4-phenylthiazole, 2-amino-4(2'tolyl)thiazole, 2-amino-4-(3'-nitrophenyl)thiazole, 2-amino-4-ethylthiazole, 2-amino-4 (4'-methoxyphenyl)thiazole, 2-amino-4-(4'-ethoxyphenyl)thiazole, 2-amino-4-(4'chlorophenyl)thiazole, 2-amino-4-(2'-methoxyphenyl)thiazole, 2-amino-4-benzylthiazole, 2-amino-4-(4'-thiomethoxyphenyl)thiazole, 2-amino-4-(3',4'-dihydroxyphenyl)thiazole, 2-amino-4-(3',4'-dimethoxyphenyl)thiazole, 2-amino-4-4-(2'-furyl)thiazole, 2-amino-4cyanothiazole, 2-amino-4-(ethoxycarbonyl)thiazole, 2-amino-4-chloro-thiazole, 2amino-4-bromo-thiazole, 2-amino-4-iodothiazole, 2-amino-4-butoxymethylthiazole, 2amino-4-vinylthiazole, 2-amino-4-(4'-toly)thiazole, 2-amino-4-(2'-nitrophenyl)thiazole, 2-amino-4-(2'-chloro-phenyl)thiazole, 2-amino-4-(4'-nitrophenyl)thiazole, 2-amino-4 (3'-chlorophenyl)thiazole, 2-amino-4-(4'-bromophenyl)thiazole, 2-amino-4-(3'-bromophenyl)thiazole, 2-amino-4-(4'-toluenesulphonylmethyl)thiazole, 2-amino-4-(2',4'-dichlorophenyl)thiazole, 2-amino-4-(2',5'-dichlorophenyl)thiazole, 2-amino-4-chloromethylthiazole and 2-amino-4-carboxythiazole.
As examples of coupling components E-H there may be mentioned acylacetarylamides such as acetoacetanilide and acetoacet-2:5-dimethoxyanilide; aminopyrazoles such as 1-phenyl-3-methyl-5-aminopyrazole; pyrazolones such as 1:3-dimethyl-5 pyrazolone but more particularly 1-phenyl-3-(methyl, carbonamido or carbomethoxy)-5pyrazolones in which the phenyl radical is optionally substituted by for example methyl, methoxy, ethoxy, chlorine, bromine, nitro, sulphonamido or acetylamino; 2:6-dihydroxy-pyridines such as 3-cyano-4-methyl-2:6-dihydroxypyridine and 1-ethyl-3cyano-4-methyl-6-hydroxypyrid-2-one, phenols such as phenol, o-cresol, resorcinol and 3-acetylaminophenol; but more especially arylamines of the naphthylamine series such as 1-naphthylamine and more particularly of the aniline series such as 2:5-dimethoxyaniline, N:N-diethylaniline, N:N-di(ss-hydroxyethyl)-m-toluidine, N:N-di(ss-cyano ethyl)-aniline, N-ethyl-N-(ss-ethoxyethyl)aniline, N:N-di(ss-methoxycarbonylethyl)-m toluidine, N-[ss-(ss'-methoxyethoxycarbonyl)ethyl]-m-toluidine, 2-methoxy-5-acetyl amino-N-[ss-(ss'-methoxyethoxycarbonyl)ethyl]aniline, N:N-di(ss-acetoxyethyl)-m toluidine, N-ethyl-N-(ss-cyanoethyl)aniline, N-ethyl-N-(#-acetoxybutyl)aniline, N-ethyl N-benzyl-m-toluidine.
N:N-di(ss-acetoxyethyl)aniline N:N-di(ss-n-propylcarbonyloxy)-m-toluidine N:N-di(ss-methoxycarbonylethyl)aniline 3-acetylamino-N:N-di(ss-methoxycarbonylethyl)aniline N:N-diethyl-m-toluidine N-ethyl-N-(ss-hydroxyethyl)-m-toluidine N-ethyl-N-(ss-methoxycarbonylethyl)aniline N-ethyl-N-(ss-methoxycarbonylethyl)-m-toluidine N-ethyl-N-(ss-acetylethyl)-m-toluidine N-ethyl-N-(p-acetoxyethyl)-m-toluidine N-ethyl-N(#-hydroxy-n-pentyl)-m-toluidine N-ethyl-N-(#-acetoxy-n-butyl)-m-toluidine N-ethyl-N-(α-methyl-ss-methoxycarbonylethyl)-m-toluidine N-ethyl-N-(γ-chloro-ss-hydroxypropyl)-m-toluidine 3-methoxy-N:N-diethylaniline 3-methoxy-N-ethyl-N-(ss-hydroxyethyl)aniline N-cyclopentylaniline N::N-di(ss-propionyloxyethyl)-m-toluidine N-ethyl-N-[ss-(ss'-methoxycarbonylethoxycarbonyl)ethyl]-m-toluidine N-ethyl-N-[ss-(ss'-cyanoethoxy)ethyl]-m-toluidine N-ethyl-N-[ss-(ss'-methoxycarbonylethylthio)ethyl]-m-toluidine N-ethyl-N-(ss-methoxyethyl)-m-toluidine N-methyl-N-(ss-hydroxyethyl)-2:5-dimethylaniline N:N-diethyl-2:5-dimethoxyaniline 3-acetylamino-N-(ss-cyanoethyl)-N-[ss-(ss'-methoxyethoxycarbonyl)ethyl]aniline 3-acetylamino-N-[ss-(ss'-ethoxyethoxycarbonyl)ethyl]aniline 3 -acetylamino-N: N-di(ss-hydroxyethyl)aniline 3-(N-ethylureido)-N: N-di(ss-acetoxyethyl)aniline N-ethyl-N-(ss-methoxycarbonyloxyethyl)aniline 3-(methylsulphenylamino)aniline 3-chloro-N-ethyl-N-(ss-chloroethyl)aniline 3-bromo-N:N-di(ss-hydroxyethyl)aniline 3-ureidoaniline 2:5-dimethyl-N-(ss-methoxycarbonylethyl)aniline 3-acetylamino-N::N-di(ss-acetoxyethyl)aniline N:N-di(ss-ethoxycarbonylethyl)-m-toluidine 2-ethoxy-S -acetylamino-N: N-ditss-acetoxyethyl)aniline 3 -chloro-N-ethyl-N-(ss-methoxycarbonyloxyethyl)aniline 2-ethoxy-5-formylamino-N-[ss-(ss'-ethoxyethoxycarbonyl)ethyl]aniline 3-(N:N-diethylureido)-N:N-diethylaniline 2-methoxy-5-acetylamino-N-ethyl-N-[ss-(ss'-methoxyethoxycarbonyl)ethyl]aniline 2-methoxy-5-acetylamino-N-[ss-(ss'-{ss"-methoxy}ethoxycarbonyl)ethyl]aniline 3-acetyl-N: N-di(p-acetoxyethyl)aniline N:N-di [ss-(p-bromobenzoyloxy)ethyl] aniline N-ethyl-N-(m-methylsulphonylbenzyl)aniline 2-methyl-5-(methylsulphonylamino)aniline N-methyl-N-(ss-cyanoethyl)aniline N-n-butyl-N-(ss-cyanoethyl)-m-toluidine N-ethyl-N-(ss:α-dihydroxypropyl)-m-toluidine N-ethyl-N-[α:ss-di(ethoxycarbonyl)ethyl]aniline N-ethyl-N-(ss-phenylethyl)aniline 3 -trifluoromethyl-N : N-diethylaniline N:N-di[ss-(cyanomethoxycarbonyl)ethyl]aniline 2-methoxy-5-benzoylamino-N:N-di(ss-acetoxyethyl)aniline 3-acetylamino-N:N-di [ss-(methylsulphonyloxy)ethyl] aniline 3-(ss-chloropropionylamino)-N:N-diethylaniline 3-(isopropionylamino)-N:N-dibenzylaniline N-ethyl-N-(ss-succinimidoethyl)-m-toluidine N-ethyl-N-[ss-(methylsulphonylamino)ethyl]-m-toluidine N-ethyl-N-(ss-ethylsulphonylethyl)-m-toluidine 3-ethoxyvarbonyl-N: N-diethylaniline 3-cyano-N: N-diethylaniline 3-ethylthio-N:N-di(ss-methoxycarbonylethyl)aniline 3-(N-ethylacetylamino)-N:N-di(ss-methoxycarbonylethyl)aniline 3-(dimethylaminosulphonylamino)-N:N-diethylaniline N-phenylmorpholine N-phenylpyrrolidine 1-(N-ss-hydroxyethylamino)naphthalene N:N-di(ss-ethoxycarbonylethyl)aniline 3-acetylamino-N,N-diethylaniline 3-acetylamino-N:N-di(ss-ethoxycarbonylethyl)aniline 3-ureido-N:N-di(ss-methoxycarbonylethyl)aniline 3-(N-methylureido)-N:N-di(ss-methoxycarbonylethyl)aniline 3-propionylamino-N::N-di(ss-methoxycarbonylethyl)aniline 3-(methoxycarbonylamino)-N:N-di(ss-methoxycarbonylethyl)aniline 3-(methylsulphonylamino)-N:N-di(ss-methoxycarbonylethyl)aniline 3-methoxy-N:N-di(ss-methoxycarbonylethyl)aniline 3-ethoxy-N:N-di(ss-methoxycarbonylethyl)aniline 3-chloro-N:N-di(ss-methoxycarbonylethyl)aniline 3-bromo-N:N-di(ss-methoxycarbonylethyl)aniline 3-cyano-N:N-di(ss-methoxycarbonylethyl)aniline 3-methylsulphonyl-N:N-di(ss-methoxycarbonylethyl)aniline 3-sulphamoyl-N:N-di(ss-methoxycarbonylethyl)aniline 2-methyl-N:N-di(ss-methoxycarbonylethyl)aniline 2-methoxy-N:N-di(ss-methoxycarbonylethyl)aniline 2-methoxy-5-methyl-N:N-di(ss-methoxycarbonylethyl)aniline N-ethyl-N-ss-cyanoethyl-m-toluidine.
2:5-dimethoxy-N:N-di(ss-methoxycarbonylethyl)aniline 2-methoxy-5-acetylamino-N:N-di(ss-methoxycarbonylethyl)aniline 3-methyl-N:N-di[ss-(ss'-methoxyethoxycarbonyl)ethyl]aniline 3-methyl-N: N-di [ss-(ss'-hydroxyethoxycarbonyl)ethyl] aniline 3-methyl-N-(ss-carboxyethyl)-N-(ss-ethoxycarbonylethyl)aniline N-ethyl-N-(ss-carboxyethyl)aniline 3 -methyl-N-(ss-cyanoethyl)-N-tR-carboxyethyl)aniline 2-methoxy-S -acetylamino-N: N-di [fiKP'-methoxyethoxycarbonyl)ethyl] aniline 3 -acetylamino-N: N-di [p-(P'-methoxyethoxycarbonyl)ethyl] aniline 3-acetylamino-N:N-di [ ss-(cyanomethoxycarbonyl)ethyl] aniline The disazo dyestuffs of the invention are valuable for colouring synthetic textile materials in particular secondary cellulose acetate and cellulose triacetate textile materials, polyamide textile materials such as polyhexamethylene adipamide textile materials, and, above all, aromatic polyester textile materials such as polyethylene terephthalate textile materials. Such materials can be in the form of filaments, fibres or woven or knitted materials.
The said disazo dyestuffs can be applied to the synthetic textile materials optionally in conjunction with other disperse dyestuffs by methods which are con ventionally employed in applying disperse dyestuffs to such textile materials. Thus the dyestuffs in the form of aqueous dispersions can be applied by dyeing, padding or printing processes using the conditions and other additives which are conventionally used in carrying out such processes. Alternatively the said dyestuffs can be applied to synthetic textile materials by solvent methods of dyeing, for example by applying a solution or dispersion of the dyestuff in perchloroethylene optionally containing a minor amount of water to the textile material preferably at elevated temperature.
The said dyestuffs can also be used in the melt colouration of synthetic polymers, for example by late injection techniques, the coloured polymers then being melt spun into fibres or filaments. The said dyestuffs can also be applied to synthetic textile materials by the process of transfer colour printing, optionally under reduced air pressure or under wet or humid conditions.
When applied to synthetic textile materials the disazo dyestuffs of the invention give orange through to greenish-blue colourations which have excellent fastness to light and to wet and to dry heat treatments, both before and after heat setting. The said dyestuffs also have high tinctorial strength, excellent dyeing, levelling, temperature range and excellent build up properties on synthetic textile materials, particularly aromatic polyester textile materials, thus enabling heavy depths of shade to be readily obtained.
The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.
Example 1.
6.37 Parts of 4-chloroaniline are dissolved in a solution containing 15 parts of concentrated hydrochloric acid and 125 parts of water. The solution is stirred and cooled to a temperature of 015"C and 25 parts of a 14% aqueous solution of sodium nitrite are then added, the temperature of the mixture being maintained between 0 C and 5"C by external cooling. The mixture is stirred for 15 minutes and is then added to a solution of 7.52 parts of 2-amino-4-methylthiazole hydrochloride in 200 parts of glacial acetic acid and 40 parts of water, simultaneously adding dropwise a 32 % aqueous solution of sodium acetate to maintain the pH of the mixture just acid to Congo Red indicator paper.The mixture is then stirred for 2 hours and the precipitate yellow solid is filtered off, washed with water and dried.
2.52 Parts of the solid intermediate prepared as described above are stirred in a mixture of 20 parts of phosphoric acid (s.g. 1.700) and 20 parts of glacial acetic acid. The mixture is cooled to 0 C and 2.6 parts of a 40% solution of nitrosyl sulphuric acid are added during 1 hour, maintaining the temperature of the mixture at 0--2"C by external cooling. The mixture is then stirred for a further 2 hours at 0-2 C and is then added to a solution of 1.7 parts of N-ethyl-N-ss-cyanoethylaniline in 40 parts of glacial acetic acid and 5 parts of water containing 0.2 part of sulphamic acid, the pH of the mixture being maintained at 1-2 by the simultaneous addition of a 32% aqueous solution of sodium acetate. The resulting mixture is stirred for 2 hours and the precipitated dyestuff is filtered off, washed with water and dried.
When dispersed in water the dyestuff dyes aromatic polyester textile material in heavy violet shades.
Example 2.
The procedure described in Example 1 is repeated except that the 1.7 parts of N-ethyl-N-ss-cyanoethylaniline are replaced by 2.06 parts of N,N-diethyl-m-aminoacetanilide.
When dispersed in water the resulting dyestuff dyes aromatic polyester textile material in greenish blue shades.
Example 3.
The procedure described in Example 1 is repeated except the 1.7 parts of N ethyl-N-ss-cyanoethylaniline are replaced by 1.88 parts of N-ethyl-N-ss-cyanoethyl-m- toluidine.
When dispersed in water the resulting dyestuff dyes aromatic polyester textile material in navy blue shades.
Example 4.
The procedure described in Example 1 is repeated except that the 1.7 parts of N-ethyl-N-fi-cyanoethylaniline are replaced by 2.65 parts of N,N-bis(acetoxyethyl) aniline.
When dispersed in water the resulting dyestuff dyes aromatic polyester textile material in violet shades.
Example 5.
The procedure described in Example 1 is repeated except that the 1.7 parts of N-ethyl-N-p-cyanoethylaniline are replaced by 2.79 parts of N,N-bis(acetoxyethyl)m-toluidine.
When dispersed in water the resulting dyestuff dyes aromatic polyester textile material in reddish blue shades.
Example 6.
6.9 Parts of 4-nitroaniline are diazotised, and coupled with 7.52 parts of 2-amino4-methylthiazole hydrochloride as described in Example 1.
To a mixture of 20 parts phosphoric acid (S.G. 1.700) and 20 parts glacial acetic acid is added, with external cooling, 5 parts of a 40% solution of nitrosyl sulphuric acid over 5 minutes. This solution is further cooled to 0"--5" and 2.63 parts of the solid intermediate prepared as described above are added over 5 minutes.
The mixture is stirred a further 25 minutes at 0 5 then added to a solution of 2.1 parts of N-ethyl-N-(p-acetoxyethyl)aniline in 40 parts glacial acetic acid and 5 parts of water containing 0.4 parts of sulphamic acid. The resulting mixture is stirred for 2 hours and the precipitated dyestuff is filtered off, washed with water and dried.
When dispersed in water the dyestuff dyes aromatic polyester textile material in blue shades.
Example 7.
The procedure described in Example 6 is repeated except that 2.06 parts of N,N-di-ethyl-m-aminoacetanilide replace the 2.1 parts of N-ethyl-N-(ss-acetoxyethyl) aniline.
When dispersed in water the resulting dyestuff dyes aromatic polyester textile materials in blue shades.
Examples 8 to 57.
The following dyestuffs are obtained by the method described in Example 1, by diazotising the amine given in the second column of Table 1 below, coupling the diazo component so obtained with the 2-aminothiazole given in the third column, diazotising the resulting azo intermediate and coupling the diazo compound so obtained with the coupling component given in the fourth column. The shade obtained when an aqueous dispersion of the dyestuff is applied to aromatic polyester textile material is given in the fifth column.
TABLE I
R I l} N Example Amine R= NH2 H2 Coupling Component Shade
8 4-chloroaniline methyl 3 -ac e ty lamino-N-e thy l-N- Reddish (ss-cyanoethyl)aniline blue 9 " " N,N-diethyl-m-toluidine Greenish blue 10 " " 3-acetylamino-N,N-bis(ss- Reddish acetoxyethyl)aniline. blue 11 4-methylaniline " N-ethyl-N-(ss-cyanoethyl)- Violet m-toluidine.
12 4-nitroan iline " 3-propiony lamino-N,N- Bluish diethylaniline green 13 " " N-ethyl-N-(ss-propionyloxy- Blue ethyl)aniline 14 " " N,N-bis(ss-acetoxyethyl)- Greenish m-toluidine blue 15 4-chloroani line hydrogen 3-acetylamino-N ,N-diethyl aniline 16 " " N,N-bis(ss-acetoxyethyl)- Reddish m-toluidine blue 17 " " N,N-diethyl-m-toluidine Greenish blue 18 " " 3-acetylamino-N,N-bis(ss hydroxyethyl)aniline 19 " " 3-acetylamino-N,N-bis(ss- Reddish acetoxyethyl)aniline blue 20 aniline methyl N-ethyl-N-(ss-cyanoethyl)- Violet m-toluidine 21 " " 3-acetylamino-N,N-diethyl- Blue aniline 22 " " N,N-bis(ss-acetoxyethyl)- Violet m-toluidine 23 " " 3-acetylamino-N,N-bis(ss- Blue hydroxyethyl)aniline 24 " " 3-acetylamino-N,N-bis(ss- Blue acetoxyethyl)aniline violet 25 " " 3-acetylamino-N-ethyl- Violet N-(ss-cyanoethyl)aniline 26 ,, N,N-diethyl-m-toluidine Blue TABLE I (Cont.)
R Example Amine R=ts)L H2 Coupling Component Shade
27 4-ch loroan i line me they l N -n-buty l-N-(ss-cyanoe thy 1)- Violet aniline 28 " N-n-buty l-N-(P-cyanoe thy 1)- Navy blue m-toluidine 29 " " 3-acetylamino-N,N-di-n- Greenish propylaniline blue 30 " " N,N-bis(ss-propionyloxy- Violet ethyl)aniline 31 ,, " N,N-bi s(P-propiony loxy- Reddish ethyl)-m-toluidine blue 32 " " N,N-bis(ss-hydroxyethyl)- Blue m-toluidine 33 " " 3-acetylamino-N,N-bis(ss- Greenish hydroxyethyl)aniline blue 34 aniline hydrogen 3-acety lamino-N,N-diethy I- Blue aniline 35 " " N,N-bis(ss-acetoxyethyl)- Violet m-toluidine 36 " " N,N-diethyl-m-toluidine Blue 37 " " 3-acety lamino-N,N-bis(P- Reddish hydroxyethyl)aniline blue 38 " " 3-acetylamino-N,N-bis(ss- Blue acetoxyethyl)aniline violet 39 4-nitroaniline " 3-acetylamino-N,N-diethyl- Bluish aniline green 40 " ,, N-ethy l-N-(P-acetoxyethy 1)- Blue aniline 41 " " N,N-bis(ss-acetoxyethyl)-m- Blue toluidine 42 " " N,N-diethyl-m-toluidine Greenish blue 43 aniline phenyl N,N-bis(ss-acetoxyethyl)-m- Reddish toluidine blue 44 " " N,N-diethyl-m-toluidine Greenish blue 45 " " 3-acetylamino-N,N-bis- Greenish (ss-hydroxyethyl)aniline blue TABLE I (Cont.)
R Example Amine R= NH2 2 Coupling Component Shade
46 aniline phenyl 3-acetylamino-N,N-bis- Blue (ss-acetoxyethyl)aniline 47 " " 3-acetylamino-N-ethyl-N- Reddish (ss-cyanoethyl)aniline blue 48 4-chloroaniline " N,N-bis(ss-acetoxyethyl)- Blue m-toluidine 49 " " N,N-diethyl-m-toluidine Bluish green 50 " " 3-acetylamino-N,N-bis- Bluish (ss-hydroxyethyl)aniline green 51 " " 3-acetylamino-N,N-bis- Greenish (ss-acetoxyethyl)aniline blue 52 " " 3-acetylamino-N-ethyl-N- Blue (ss-cyanoethyl)aniline 53 4-nitroaniline " 3-acetylamino-N,N-diethyl- Green aniline 54 " " N-ethyl-N-(ss-acetoxy- Greenish ethyl)aniline blue 55 " " N,N-bis(ss-acetoxyethyl)- Greenish m-toluidine blue 56 " " N,N-diethyl-m-toluidine Green 57 " " N-ethy l-N-(B-cyanoethyl)- Greenish m-toluidine blue Examples 58 to 160.
The following dyestuffs are obtained by the method described in Example 1, by diazotising the amine given in the second column of Table 2 below, coupling the diazo component so obtained with 2-amino-4-methylthiazole, diazotising the resulting azo intermediate and coupling the diazo compound so obtained with the coupling component given in the third column. The shade obtained when an aqueous dispersion of the dyestuff is applied to aromatic polyester textile material is given in the fourth column.
TABLE 2
Example Amine Coupling Component Shade 58 2-bromo-4-nitroaniline N-ethyl-N-(ss-cyanoethyl)- Greenish-blue m-toluidine 59 4-cyanoaniline " Blue 60 2-cyano-4-ni troan iline " Bluish-green 61 4-nitro-2-(trifluoro- " Greenish-blue methyl)aniline 62 2,4-dicyanoaniline " Greenish-blue 63 3-nitroaniline " Reddish-blue 64 4-me thy 1-2 -nitroaniline " Blue 65 2-methoxy-4-nitroaniline " Greenish-blue 66 4-(methylsulphonyl)aniline " Reddish-blue 63 2-chloro-4-(methylsulphonyl)- " Blue aniline 68 2-chloro-4-nitroaniline " Greenish-blue 69 4-aminoacetophenone " Reddish-blue 70 4-aminobenzaldehyde " Blue 71 4-e thoxy carbony lan i line N-ethy l-N-(ss-cy ano- Reddish-blue ethyl)aniline 72 4-(ss-methoxyethoxy)- " " carbony laniline 73 4-(aminosulphonyl)aniline line 74 4-(N,N-dimethylamino- " " sulphonyl)aniline 75 4-(aminocarbonyl)aniline " " 76 4-(N-ethylaminocarbonyl)aniline " " 77 4-aminoacetanilide 78 3-(N,N-dimethylamino- " Violet sulphonyloxy)aniline 79 2-amino-3,5-dini trothiophene " Green 80 2-amino-3-nitro-5-acetylthiophene " 81 2-amino-3-methoxy-carbonyl- " " " 5-nitrothiophene 82 2-amino-3-cyano-5-nitro- " thiophene 83 2-amino-3,5-dicyano-4- " " methylthiophene TABLE 2 (Cont.)
Example Amine Coupling Component | Shade 84 2-amino-5-nitrothiazole N-ethyl-N-(B-cyanoethyl)- Green aniline 85 5-amino-3 -phenyl- " Greenish-blue 1,2,4-thiadiazole 86 2-amino-6-methyl- ,, Bluish-green sulphonylbenzothiazole 87 2-amino-6-thiocyanatobenzo- " " thiazole 88 2-amino-6-nitrobenzothiazole ,, Green 89 2-amino-6-chlorobenzothiazole " Greenish-blue 90 2-amino-6-methoxybenzo- " " thiazole 91 2-aminobenzothiazole 92 3-amino-5-nitrobenzo- ,, Green 2,1-isothiazole 93 2,5-dichloroaniline " Blue-violet 94 2,4, 5-trichloroani line " Reddish-blue 95 4-chloroaniline 2-me thoxy-5-methy l-N,N- Greenish-blue bis(ss-acetoxyethyl)aniline 96 " 2-me thy 1-N-(ss-cyanoethyl)- Violet aniline 97 " 2-chloro-N-(ss-hydroxy ethyl)ani line 98 " 2-me thoxy-5-me thy l-N-n- Greenish-blue butylaniline 99 ,, 3-aminoacetanilide Bluish-violet 100 " 3-acetylaminoN-ethyl- Blue aniline 101 " 3-acetylamino-N,N-bis- Reddish-blue (ss-methoxycarbonyl ethyl)aniline 102 " 2,5-dimethoxy-N,N-bis- Greenish-blue (ss-acetoxyethyl)aniline 103 " 3-chloro-N,N-bis(ss- Reddish-blue hydroxyethyl)aniline 104 ,, 3-bromo-N,N-bi s(P-methoxy- Violet carbony lethyl)aniline 105 " 3-trifluoromethyl-N,N-bis- " (ss-acetoxyethyl)aniline TABLE 2 (Cont.)
Example Amine Coupling Component Shade 106 4-chloroaniline 3-cyano-N,N-bis(ss-acetoxy- Violet ethyl)aniline 107 " 3-(methylsulphonyl)-N,N- Reddish-blue diethylaniline 108 " 3-(ethylaminosulphonyl)- Violet N,N-bis(ss-acetoxyethyl) aniline.
109 " 3-(aminosulphonyl)-N,N- Reddish-blue diethylaniline 110 ,, 3-(dimethy laminosulphonyl)- Violet N,N-bis(-acetoxyethyl)- aniline 111 ,, 3-(propiony lamino)-N ,N- Greenish-blue diethylaniline 112 " 3-(ss-methoxyethoxycarbonyl amino)-N ,N-diethylaniline 113 ,, 3-benzoylamino-N,N-bis- " (ss-hydroxyethyl)aniline 114 " 3-formylamino-N,N-bis- Reddish-blue (ss-acetoxyethyl)aniline 115 ,, 3-ureidoN ,N-diethyl- Greenish-blue aniline 116 " 3-(ethylaminocarbonylamino)- " N,N-diethylaniline 117 " 3-(pheny laminocarbonyl- Reddish-blue amino)-N,N-bis(ss-acetoxy ethy l)ani line 118 ,, 5-acety lamino-2-ethoxy- Greenish-blue N,N-bis(B-acetoxyethyl)- aniline 119 " 5-acetylamino-2-methoxy- Bluish-green N,N-diethylaniline 120 " 5-acetylamino-2-methoxy- Greenish-blue N-ethylaniline 121 " 3-acetylaminoN-(ss-methoxy- Reddish-blue carbonylethyl)aniline 122 ,, 3-acetylamino-N-[ss-(ss'- Bluish-violet ethoxyethoxycarbonyl) ethyl]aniline.
123 " 3-acetylamino-N-(ss-cyano- " ethyl)N-(ss-methoxycarbonyl ethyl)aniline.
TABLE 2 (Cont.)
Example Amine Coupling Component Shade 124 4-chloroaniline 3-acetylamino-N-(ss-cyanoethyl)- Bluish-violet N-[(ss-methoxyethoxycarbonyl) ethyl] aniline 125 ,, 3-(ethoxycarbonylamino)-N,N- Greenish-blue diethylaniline 126 " 3-(methoxycarbonylamino)- Reddish-blue N,N-bis(ss-methoxycarbonyl ethyl)aniline 127 " N-ethyl-N-(ss-hydroxyethyl)- Blue aniline 128 " 3-methyl-N-ethyl-N-(ss,γ-di- " hydroxypropyl)aniline 129 ,, 3-methyl-N-ethyl-N-(y-chloro 129 " @-methyl@@@ethyl@@@(γ;-chloro- " ss-hydroxypropyl)aniline 130 " N,N-bis(ss-methoxyethyl)aniline " 131 " 3-methyl-N-(ss-cyanoethyl)- Reddish-blue N-(ss-ethoxyethyl)aniline 132 " 3-acetylamino-N-(ss-cyanoethyl)- " N-(y-methoxypropy I) aniline 133 " N-benzyl-N-(ss-cyanoethyl)- Violet aniline 134 " 3-methyl-N-(ss-acetoxyethyl)- Reddish-blue N-(ss-phenylethyl)aniline 135 ,, N ,N-bi s(ss-me thoxy carbony lethy l)- Violet aniline 136 ,, 3-methyl-N,N-bi s(P-ethoxy- Reddish-blue carbonylethyl)aniline 137 " 5-acetylamino-2-methoxy-N,N- Greenish-blue bis(ss-methoxycarbonylethyl) aniline 138 ,, N-(ss-cyanoethyl)-N-(ss-ethoxy- Violet carbonylethyl)aniline 139 " N-(ss-cyanoethyl)-N-(ss-acetoxy ethyl)aniline 140 " N-(ss-cyanoethyl)-N-(ss-phenoxy- " ethyl)aniline 141 ,, N-e thy l-N-[(P-cyanomethoxy- Reddish-blue carbonyl)ethyl]aniline 142 " N-(ss-cyanoethyl)-N-[(ss- Violet hydroxyethoxycarbonyl) ethyl]aniline TABLE 2 (Cont.)
Example | Amine Coupling Component Shade 143 4-chloroaniline N-(ss-cyanoethyl)-N-[(ss- Violet acetoxyethoxycarbonyl) ethyl]aniline 144 " 5-acetylamino-2-methoxy- Greenish-blue N-[(ss-methoxyethoxycarbonyl) ethy Ijaniline 145 " 5-acetylamino-2-methoxy- Bluish-green N-ethyl-N-[(ss-methoxyethoxy carbonyl)ethyl]aniline 146 " 3-methyl-N,N-bis[(ss-ethoxy- Reddish-blue carbonyloxy)ethyl]aniline 147 " 3-methyl-N-(ss-cyanoethyl)- Violet N-[(ss-methylcarbonyl)ethyl] aniline 148 " N-ethyl-N-[ss-(ss'-cyanoethoxy)- Reddish-blue ethyl]aniline 149 " 3-acetylamino-N-ethyl-N-{ss-[ss'-Bluish-violet (ss"-methoxyethoxy)ethoxy carbonyl]ethyl laniline 150 ,, 3-methy l-N-ethy 1-N-(ss- Reddish-blue ethylsulphonylethy I)aniline 151 ,, 3-methy I-N-ethy 1-N-[(ss-ethy 1- Blue aminocarbonyloxy)ethyl]aniline 152 ,, acetoacetanilide Yellow 153 " 1 -pheny 1-3-methy 1-5-pyrazolone Orange 154 ,, 1-phenyl-3-methyl-5-amino- Red pyrazole 155 ,, 3-methyl-5-pyrazolone Yellow 156 ,, 3-cyano-4-methy 1-6-hydroxy- Yellow pyrid-2-one 157 ,, 1-ethyl-3-cyano-4-methyl-6- Yellow hydroxypyrid-2-one 158 " 1-n-butyl-3-cyano-4-methyl- Yellow 6-hydroxypyrid-2-one 159 " 6hydroxypyrid-2-one phenol Yellow 160 ,, o-cresol Yellow Examples 161 to 187.
The following dyestuffs are obtained by the method described in Example 1, by diazotising the amine given in the second column of Table 3 below, coupling the diazo component so obtained with the 2-aminothiazole given in the third column, diazotising the resulting azo intermediate and coupling the diazo compound so obtained with the coupling component given in the fourth column. The shade obtained when an aqueous dispersion of the dyestuff is applied to aromatic polyester textile material is given in the fifth column.
TABLE 3
B Example Amine R= \JL 2 Coupling Component Shade
161 2-cyano-4,6- methyl N-ethy!-N-(ss-cyano-ethyl)- Green dinitroaniline m-toluidine 162 2,6-dicyano-4- " N-n-butyl-N-((3-cyanoethyi) nitroaniline m-toluidine 163 4-chloroaniline " ss-naphthol Violet 164 ,, " a-naphthol 165 ,, " diphenylamine 166 " " N-cyclohexylaniline 167 " " N-(ss-hydroxyethyl)-α;- Greenish naphthylamine blue 168 " " 8-(ss-hydroxyethyl)- aminoquinoline 169 4-aminodi- " N-ethyl-N-(ss-cyanoethyl)- " phenyl- aniline sulphone 170 4-chloroaniline " 3-benzoylamino-N,N- Reddish bis(ss-acetoxyethyl)- blue aniline 171 " " N-ethyl-N-(ss-phenoxy- Blue ethyl)m-toluidine 172 " " N-(ss-acetoxyethyl)-N- Bluish (ss-phenoxyethyl)- violet aniline 173 " " N-ethyl-N-(ss-p-tolyl- Reddish sulphonylethyl)m- blue toluidine 174 " 4-methoxyphenyl N-ethy 1-N-(ss-cyano- Blue ethy l)-m-toluidine 175 " 4-tolyl 176 " 2-nitrophenyl 177 ,, 3-nitrophenyl 178 " 4-chlorophenyl 179 " 3-chlorophenyl ,, 180 " 2-chlorophenyl N-ethyl-N-(ss-cyanoethyl)- ' m-toluidine TABLE 3 (Cont.)
~ R N {;rn;;};;mine R1 NH2 Coupling Component Shade
181 4-chloro- 4-bromophenyl N-ethyl-N-(ss-cyanoethyl)- Blue aniline m-toluidine 182 " 3-bromophenyl 183 " p-tolylsulphonyl methyl 184 " 2,4-dichloro phenyl 185 " 2,5-dichlorophenyl 186 " ethyl " Reddish blue 187 " cyano " " Specification No. 1,519,680 describes and claims A disazo-thiazole dyestuff which in the form of the free acid corresponds to the general formula
in which D denotes a radical of an aromatic carbocyclic or heterocyclic diazo component, K denotes a radical of a carbocyclic or heterocyclic coupling component, A and B independently denote a direct bond or a bridge member, R1 denotes a hydrogen atom or a C1 to C4 alkyl, optionally substituted phenyl or naphthyl, carbon, to C4 alkoxy, cyano or an optionally substituted carboxamide group in which the substituents may form with the N atom a piperidine, pyrrolidine or morpholine ring, R2 denotes a C1 to C4 alkyl or optionally substituted phenyl or naphthyl radical and m and n are 0, 1 or 2, and the sum of m and n is 1 or 2.
We make no claim to any dyestuff claimed in Specification No. 1,519,680.
Subject to the above disclaimer.
WHAT WE CLAIM IS: 1. A disazo dyestuff, devoid of ionic water-solubilising groups and having the formula:
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (18)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    TABLE 3 (Cont.)
    ~ R N {;rn;;};mine R1 NH2 Coupling Component Shade
    181 4-chloro- 4-bromophenyl N-ethyl-N-(ss-cyanoethyl)- Blue aniline m-toluidine 182 " 3-bromophenyl 183 " p-tolylsulphonyl methyl 184 " 2,4-dichloro phenyl 185 " 2,5-dichlorophenyl 186 " ethyl " Reddish blue 187 " cyano " " Specification No. 1,519,680 describes and claims A disazo-thiazole dyestuff which in the form of the free acid corresponds to the general formula
    in which D denotes a radical of an aromatic carbocyclic or heterocyclic diazo component, K denotes a radical of a carbocyclic or heterocyclic coupling component, A and B independently denote a direct bond or a bridge member, R1 denotes a hydrogen atom or a C1 to C4 alkyl, optionally substituted phenyl or naphthyl, carbon, to C4 alkoxy, cyano or an optionally substituted carboxamide group in which the substituents may form with the N atom a piperidine, pyrrolidine or morpholine ring, R2 denotes a C1 to C4 alkyl or optionally substituted phenyl or naphthyl radical and m and n are 0, 1 or 2, and the sum of m and n is 1 or 2.
    We make no claim to any dyestuff claimed in Specification No. 1,519,680.
    Subject to the above disclaimer.
    WHAT WE CLAIM IS: 1. A disazo dyestuff, devoid of ionic water-solubilising groups and having the formula:
    wherein A represents the residue of a diazo component; E represents the residue of a coupling component and R represents hydrogen or a substituent.
  2. 2. A dyestuff as claimed in claim 1 wherein A is an optionally substituted aryl or heterocyclic radical.
  3. 3. A dyestuff as claimed in claim 2 wherein the optionally substituted aryl radical is an optionally substituted phenyl radical.
  4. 4. A dyestuff as claimed in any one of claims 1 to 3 wherein E has the formula:
    where Rl and R2 each independently represent a hydrogen atom or an optionally substituted hydrocarbon radical, and the benzene ring B may contain additional substituents or form part of an optionally further substituted naphthalene or quinoline ring.
  5. 5. A dyestuff as claimed in claim 4 wherein the optionally substituted hydrocarbon radical represented by R1 and R2 in an optionally substituted lower alkyl radical.
  6. 6. A dyestuff as claimed in any one of claims 1 to 3 wherein E has the formula:
    wherein W is hydrogen, lower alkyl or lower alkoxy, V is hydrogen, lower alkyl, lower alkoxy, chlorine, bromine, trifluoromethyl, cyano, acylamino or --SOzT3 wherein T3 is optionally substituted lower alkyl or aryl, R1 is hydrogen or an optionally substituted alkyl radical and R4 is hydrogen or an optionally substituted alkyl, optionally substituted aryl or a cycloalkyl radical.
  7. 7. A dyestuff as claimed in claim 6 wherein the acylamino radical represented by V has the formula -NHCOT2 or -NHSO1T3, wherein T2 is hydrogen, alkyl, aryl or -NHT4, T3 has the meaning stated in claim 6 and T4 is hydrogen, alkyl or aryl.
  8. 8. A dyestuff as claimed in claim 6 or claim 7 wherein the optionally substituted alkyl radicals represented by R3 and Rl, and the alkyl radicals represented by T2 and T4, are optionally substituted lower alkyl radicals and lower alkyl radicals respectively.
  9. 9. A disazo dyestuff, devoid of ionic water-solubilising groups, substantially as hereinbefore described in any one of the foregoing Examples 1 to 5.
  10. 10. A disazo dyestuff, devoid of ionic water-solubilising groups, substantially as hereinbefore described in any one of the foregoing Examples 6 to 187.
  11. 11. A process for the manufacture of the disazo dyestuffs claimed in claim 1 which comprises diazotising an amine of the formula A-NH2, wherein A has the meaning stated in claim 1, coupling the resulting diazo compound with a 2-aminothiazole of the formula:
    wherein R has the meaning stated in claim 1, diazotising the azo intermediate of the formula:
    so obtained and coupling the resulting diazo compound with a coupling component of the formula E-H wherein E has the meaning stated in claim 1.
  12. 12. A process for the manufacture of disazo dyestuffs substantially as hereinbefore described in any one of the foregoing Examples 1 to 5.
  13. 13. A process for the manufacture of disazo dyestuffs substantially as hereinbefore described in any one of the foregoing Examples 6 to 187.
  14. 14. Disazo dyestuffs whenever obtained by a process as claimed in claim 11 or claim 12.
  15. 15. Disazo dyestuffs whenever obtained by a process as claimed in claim 13.
  16. 16. A process for the colouration of synthetic textile materials which comprises applying to the synthetic textile material by a dyeing, padding or printing process an aqueous dispersion of a disazo dyestuff as claimed in claim 1.
  17. 17. A process as claimed in claim 16 wherein the synthetic textile material is an aromatic polyester textile material.
  18. 18. Coloured synthetic textile materials whenever obtained by a process as claimed in claim 16 or claim 17.
GB16167/77A 1977-04-19 1977-04-19 Disazo-thiazole dyestuffs Expired GB1589927A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB16167/77A GB1589927A (en) 1977-04-19 1977-04-19 Disazo-thiazole dyestuffs
DE19782816629 DE2816629A1 (en) 1977-04-19 1978-04-17 DISAZO DYES
IT22406/78A IT1174363B (en) 1977-04-19 1978-04-17 DIAZIOIC COLARANTS THAT CONTAIN A HETEROCYCLIC CORE
JP4582078A JPS53130729A (en) 1977-04-19 1978-04-18 Heterocycliccnucleusscontaining disazo dye* containing no ionic* waterrsoluble group method of making same and dyeing synthetic fiber material using same
FR7811419A FR2388025A1 (en) 1977-04-19 1978-04-18 DISPERSED BIS-AZOIC DYES DERIVED FROM 2-AMINOTHIAZOLE
ES468949A ES468949A1 (en) 1977-04-19 1978-04-19 Disazo-thiazole dyestuffs

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GB1589927A true GB1589927A (en) 1981-05-20

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JP (1) JPS53130729A (en)
DE (1) DE2816629A1 (en)
ES (1) ES468949A1 (en)
FR (1) FR2388025A1 (en)
GB (1) GB1589927A (en)
IT (1) IT1174363B (en)

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* Cited by examiner, † Cited by third party
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DE2910806A1 (en) * 1979-03-20 1980-10-02 Basf Ag THIAZOL SERIES DYES
JPS57177060A (en) * 1981-04-24 1982-10-30 Mitsubishi Chem Ind Ltd Disazo dye for polyester fiber
DE3321518A1 (en) * 1983-06-15 1984-12-20 Basf Ag, 6700 Ludwigshafen ISOTHIAZOLDISAZO DYES
GB8704727D0 (en) * 1987-02-27 1987-08-05 Ici Plc Aromatic disazo compound

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US3158435A (en) * 1959-12-24 1964-11-24 Montedison Spa Process for dyeing polyolefins
DE2438496A1 (en) * 1974-08-10 1976-02-26 Bayer Ag DISAZO DYES
DE2640542A1 (en) * 1976-09-09 1978-03-23 Basf Ag AZO DYES

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ES468949A1 (en) 1978-12-16
IT7822406A0 (en) 1978-04-17
DE2816629A1 (en) 1978-10-26
JPS53130729A (en) 1978-11-15
FR2388025A1 (en) 1978-11-17

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