DE2211663B2 - Azo dyes - using 2,6-diaminopyridine deriv coupling component - Google Patents
Azo dyes - using 2,6-diaminopyridine deriv coupling componentInfo
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- DE2211663B2 DE2211663B2 DE19722211663 DE2211663A DE2211663B2 DE 2211663 B2 DE2211663 B2 DE 2211663B2 DE 19722211663 DE19722211663 DE 19722211663 DE 2211663 A DE2211663 A DE 2211663A DE 2211663 B2 DE2211663 B2 DE 2211663B2
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
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- 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
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
- C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
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- 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
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- 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
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
- C09B62/82—Azo dyes
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Abstract
Description
NH-RNH-R
in der D der Rest einer Diazokomponente der Benzol-, Naphthalin-, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe, X Cyan oder Carbonamid, einer der Reste R Phenyl und der andere Rest R Wasserstoff oder gegebenenfalls durch Hydroxy, Methoxy, Äthoxy, Hydroxyalkoxy *> mit 2 bis 4 C-Atomen, Methoxyäthoxy, Acyloxy mit 1 bis 4 C-Atomen oder Acyloxyalkoxy mit 2 bis 4 C-Atomen in der Alkoxygruppe sowie 1 bis 4 C-Atomen in der Acylgnippe substituiertes Alkyl mit 1 bis 6 C-Atomen sind. »5in D the remainder of a diazo component of the benzene, naphthalene, benzthiazole, benzisothiazole, Thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series, X cyano or Carbonamide, one of the radicals R is phenyl and the other radical R is hydrogen or optionally by hydroxy, methoxy, ethoxy, hydroxyalkoxy *> with 2 to 4 carbon atoms, methoxyethoxy, acyloxy with 1 to 4 carbon atoms or acyloxyalkoxy with 2 to 4 carbon atoms in the alkoxy group and 1 to 4 carbon atoms in the acyl group Are alkyl with 1 to 6 carbon atoms. »5
2. Ein Verfahren zur Herstellung von Azofarbstoffen der im Anspruch 1 angegebenen Formel, dadurch gekennzeichnet, daß man Diazoniumverbindungen von Aminen der allgemeinen Formel 2. A process for the preparation of azo dyes of the formula given in claim 1, characterized in that one diazonium compounds of amines of the general formula
D-NH,D-NH,
mit Kupplungskomponenten der allgemeinen Formel CH3
Xwith coupling components of the general formula CH 3
X
RHNRHN
NHRNHR
umsetzt und hydroxylgruppenhaltige Farbstoffe gegebenenfalls verestert, wobei in den Formeln D, X und R die im Anspruch 1 angegebenen Bedeutungen haben.reacted and hydroxyl-containing dyes optionally esterified, where in the formulas D, X and R have the meanings given in claim 1.
3. Farbstoffzubereitungen zum Färben von Polyamiden, Acrylnitrilpolymerisaten oder Polyestern, enthaltend neben üblichen Bestandteilen Azofarbstoffe gemäß Anspruch 1.3. Dyestuff preparations for dyeing polyamides, acrylonitrile polymers or polyesters, containing, in addition to the usual constituents, azo dyes as claimed in claim 1.
SSSS
Die Erfindung betrifft Azofarbstoffe mit 2,6-Diaminopyridinen als Kupplungskomponenten der allgemeinen FormelThe invention relates to azo dyes with 2,6-diaminopyridines as coupling components of the general type formula
D-N=ND-N = N
(D
R-HN NH-R (D
R-HN NH-R
in der D der Rest einer Diazokomponente der Benzol-, Naphthalin-, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe, X Cyan oder Carbonamid, einer der Reste R Phenyl und der andere Rest R Wasserstoff oder gegebenenfalb durch Hydroxy, Methoxy, Äthoxy, Hydroxyalkoxy mit 2 bis 4 C-Atomen, Methoxyäthoxy, Acyloxy mit 1 bis 4 C-Atomen oder Acyloxyalkoxy mit 2 bis 4 C-Atomen in der Alkoxygruppe sowie 1 bis 4 C-Atomen in der Acylgnippe substituiertes Alkyl mit 1 bis 6 C-Atomen sind, ein Verfahren zur Herstellung dieser Azofarbstoffe, das dadurch gekennzeichnet ist, daß man Diazoniumverbindungen von Aminen der allgemeinen Formelin D the remainder of a diazo component of the benzene, Naphthalene, benzothiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or Anthraquinone series, X cyano or carbonamide, one of the radicals R is phenyl and the other radical R is hydrogen or optionally by hydroxy, methoxy, ethoxy, hydroxyalkoxy with 2 to 4 carbon atoms, methoxyethoxy, Acyloxy with 1 to 4 carbon atoms or acyloxyalkoxy with 2 to 4 carbon atoms in the alkoxy group and 1 to 4 carbon atoms in the acyl group are substituted alkyl having 1 to 6 carbon atoms Process for the preparation of these azo dyes, which is characterized in that one diazonium compounds of amines of the general formula
D-NH,D-NH,
(H)(H)
mit Kupplungskomponenten der allgemeinen Formel CH3 with coupling components of the general formula CH 3
AAAA
RHN NHRRHN NHR
umsetzt und hydroxylgruppenhaltige Farbstoffe gegebenenfalls verestert, wobei in den Formeln D, X und R die vorstehend angegebenen Bedeutungen haben, sowie Farbstoffzubereitungen zum Färben von Polyamiden, Acrylnitrilpolymeiisaten oder Polyestern, enthaltend neben üblichen Bestandteilen die vorstehend genannteu Farbstoffe.reacted and hydroxyl-containing dyes optionally esterified, where in the formulas D, X and R have the meanings given above, as well as dye preparations for dyeing of polyamides, acrylonitrile polymers or polyesters containing, in addition to the usual components, the the aforesaid dyes.
Gegenüber nächstvergleichbaren aus der USA.-Patentschrift 2029 315 und der deutschen Offenlegungsschrift 1917 278 bekannten Farbstoffen haben die neuen Farbstoffe in unvorhersehbarem Maße Vorteile in der Farbstärke, Lichtechtheit und Thermofixierechtheit.Compared to the next comparable from the USA patent specification 2029 315 and the German Offenlegungsschrift 1917 278 known dyes the new dyes have unpredictable advantages in terms of color strength, lightfastness and Thermoset fastness.
Als Substituenten für die Reste D der D'azokomponenten sind beispielsweise zu nennen: in der Benzolreihe: Chlor, Brom, Nitro, Cyan, Trifluormethyl, Methylsulfonyl, Äthylsulfonyl, Phenylsulfonyl, Carbomethoxy, Carbobutoxy, Carbo- β -methoxy -äthoxy, Carbo-/?-hydroxy-äthoxy, gegebenenfalls N-mono- oder N-disubstituiertes Carbon- oder Sulfonamid, Methyl, Äthyl, Methoxy oder Äthoxy.Examples of substituents for the radicals D of the D'azo components are: in the benzene series: chlorine, bromine, nitro, cyano, trifluoromethyl, methylsulphonyl, ethylsulphonyl, phenylsulphonyl, carbomethoxy, carbobutoxy, carbo- β- methoxy-ethoxy, carbo- / ? -hydroxy-ethoxy, optionally N-mono- or N-disubstituted carbon or sulfonamide, methyl, ethyl, methoxy or ethoxy.
N-Substituenten der Carbon- oder Sulfonamide sind dabei z. B. Methyl, Äthyl, Propyl, Butyl, /ϊ-Hydroxyäthyl, γ- Hydroxy -propyl, β- Methoxy äthyl, y-Methoxy-propyl oder y-Äthoxypropyl sowie das Pyrrolidid, Piperidid oder Morpholid.N-substituents of the carbon or sulfonamides are z. B. methyl, ethyl, propyl, butyl, / ϊ-hydroxyethyl, γ- hydroxy-propyl, β- methoxy ethyl, y-methoxypropyl or y-ethoxypropyl and the pyrrolidide, piperidide or morpholide.
In der Azobenzolreihe: Chlor, Brom, Nitro, Cyan, Methyl, Äthyl, Methoxy oder Äthoxy. In der Naphthalinreihe: Nitro, in den genannten heterocyclischen Reihen: Chlor, Brom, Nitro, Cyan, Methyl, Äthyl, Phenyl, Methoxy, Äthoxy, Methylmercapto, /i-Carbomethoxy-äthyl-mercapto, /ϊ-Carboäthoxy-äthylmercapto, Carbomethoxy, Carboäthoxy, Acetyl, Methylsulfonyl oder Äthylsulfonyl.In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy. In the naphthalene series: Nitro, in the named heterocyclic series: chlorine, bromine, nitro, cyano, methyl, ethyl, Phenyl, methoxy, ethoxy, methyl mercapto, / i-carbomethoxy-ethyl-mercapto, / ϊ-Carboethoxy-ethylmercapto, carbomethoxy, carboethoxy, acetyl, methylsulfonyl or ethylsulfonyl.
Der Rest D leitet sich im einzelnen z. B. von folgenden Aminen ab: Anilin o-, m- oder p-Toluidin, o-, m- oder p-Nitroanilin, o-, m- oder p-Cyananilin, 2,4-Dicyananilin, o-, m- oder p-Chloranilin, o-, m- oder p-Bromanilin, 2,4,6-Tribromanilin, 2-Chlor-4 - nitroanilin, 2 - Brom - 4 - nitroanilin, 2 - Cyan-4 - nitroanilin, 2 - Methylsulfonyl - 4 - nitroanilin,The remainder D is derived in detail z. B. of the following amines: aniline o-, m- or p-toluidine, o-, m- or p-nitroaniline, o-, m- or p-cyananiline, 2,4-dicyaniline, o-, m- or p-chloroaniline, o-, m- or p-bromoaniline, 2,4,6-tribromaniline, 2-chloro-4 - nitroaniline, 2 - bromo - 4 - nitroaniline, 2 - cyano-4 - nitroaniline, 2 - methylsulfonyl - 4 - nitroaniline,
IO 1,3,4 - thiadiazol, 3 - Methylmercapto - 5 - amino-1,2,4 - thiadiazol, 3 - β - Carbomethoxy - äthylmercapto-5-amino-l ,2,4-tniadiazol. IO 1,3,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3- β -carbomethoxy-ethylmercapto-5-amino-1,2,4-tniadiazole.
Geeignete Diazokomponenten der Aminoazobenzolreihe sind beispielsweise:Suitable diazo components of the aminoazobenzene series are, for example:
4-Aminoazobenzol,4-aminoazobenzene,
2',3-Dimethyl-4-aminoazobenzol,2 ', 3-dimethyl-4-aminoazobenzene,
3',2-Dimethyl-4-aminoazobenzol,3 ', 2-dimethyl-4-aminoazobenzene,
2,5-Dimethyl-4-aminoazobenzol,2,5-dimethyl-4-aminoazobenzene,
2-Methyl-5-methoxy-4-aminoazobenzol,2-methyl-5-methoxy-4-aminoazobenzene,
2-iviethyl-4',5-dimethoxy-4-aminoazobc3zol,2-iviethyl-4 ', 5-dimethoxy-4-aminoazobc3zol,
^-CbJor^-metbyl-S-methoxy-^aminoazobenzol,^ -CbJor ^ -metbyl-S-methoxy- ^ aminoazobenzene,
4r-Niiro-2-methyl-5-metooxy-4-aminoazobenzol,4 r -Niiro-2-methyl-5-metooxy-4-aminoazobenzene,
4'-Chlor-2-methyl-4-aminoazobenzol,4'-chloro-2-methyl-4-aminoazobenzene,
2>5-Dimethoxy-4-aminoazobenzol,2 > 5-dimethoxy-4-aminoazobenzene,
4'-Chlor-2,5-dimethoxy-4-aminoazobenzol,4'-chloro-2,5-dimethoxy-4-aminoazobenzene,
4 '-Nitro-2,5-dimethoxy-4-aminoazobenzoL4'-nitro-2,5-dimethoxy-4-aminoazobenzoL
4'-Cblor-2,5-dimethyl-4-aminoazobenzol,4'-Cblor-2,5-dimethyl-4-aminoazobenzene,
4'..Methoxy-2,5-dimethyl-4-aminoazobenzol,4 '.. methoxy-2,5-dimethyl-4-aminoazobenzene,
4'-Nitro-4-aminoazobenzol,4'-nitro-4-aminoazobenzene,
S^Dibrom^amin, 2,3'-Dichlor-4-aminoazobenzol, S-Methoxy-^aminoazobenzol.S ^ dibrom ^ amine, 2,3'-dichloro-4-aminoazobenzene, S-methoxy- ^ aminoazobenzene.
Als Reste R sind neben Phenyl und Wasserstoff z. B. zu nennen: die Alkylreste Methyl, Äthyl, Propyl oder Butyl, die Hydroxyalkylreste, 0-Hydroxyathyl oder -propyl, rHydroxypropyl, ω-Hydroxyhexyl, so-As radicals R are in addition to phenyl and hydrogen, for. B. to mention: the alkyl radicals methyl, ethyl, propyl or butyl, the hydroxyalkyl radicals, 0-hydroxyethyl or -propyl, r hydroxypropyl, ω-hydroxyhexyl, so-
— CH2 — CH2 — O- CH 2 - CH 2 - O
2 - Methyl - 4 - nitroanilin, 2 - Methoxy - 4 - nitroanilin 4 - Chlor - 2 - nitroanilin, 4 - Methyl - 2 - nitroanilin! 4. Methoxy - 2 - nitroanilin, 1 - Amino - 2 - trifluormethyl - 4 - chlorbenzol, 2 - Chlor - 5 - amino - benzonitril, 2 - Amino - 5 - chlorbenzonitril, 1 - Amino-2 - nitrobenzol - 4 - sulfonsäure - η - butylamid oder .β - methoxyäthylamid, 2,4 - Dinitroanilin, 2,4 - Dinitro - 6 - chloranilin, 2,4 - Dinitro - 6 - bromanilin,2 - methyl - 4 - nitroaniline, 2 - methoxy - 4 - nitroaniline 4 - chlorine - 2 - nitroaniline, 4 - methyl - 2 - nitroaniline! 4.Methoxy - 2 - nitroaniline, 1 - amino - 2 - trifluoromethyl - 4 - chlorobenzene, 2 - chloro - 5 - amino - benzonitrile, 2 - amino - 5 - chlorobenzonitrile, 1 - amino-2 - nitrobenzene - 4 - sulfonic acid - η - butylamide or .β - methoxyethylamide, 2,4 - dinitroaniline, 2,4 - dinitro - 6 - chloraniline, 2,4 - dinitro - 6 - bromaniline,
2.4 - Dinitro - 6 - cyananilin, 1 - Amino - 2,4 - dinitrobenzol - 6 - methylsulfon, 2,6 - Dichlor - 4 - nitroanilin, 2,6-Dibrom-4-nitroanilin, 2-Chlor-6-brom-4-nitroanilin, 2,6-Dicyan-4-nitroanilin, 2 - Cyan - 4 - nitro-6 - chloranilin, 2 - Cyan - 4 - nitro - 6 - bromanilin, 1 - Aminobenzol - 4 - methylsulfon, 1 - Amino - 2,6 - dibrom - benzol - 4 - methylsulfon, 1 - Amino - 2,6 - di- 15 chlorbenzol-4-methylsulfon, 1 - Amino -2,4- dinitrobenzol - 6 - carbonsäure - methylester oder -/< - methoxyäthylester, 3,5- Dichloranthranilsäure - propylester,2.4 - dinitro - 6 - cyananiline, 1 - amino - 2,4 - dinitrobenzene - 6 - methylsulfone, 2,6 - dichloro - 4 - nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2 - cyano - 4 - nitro-6 - chloroaniline, 2 - cyano - 4 - nitro - 6 - bromaniline, 1 - aminobenzene - 4 - methylsulfone, 1 - amino - 2,6 - dibromo - benzene - 4 - methylsulfone, 1 - amino - 2,6 - di - 15 chlorobenzene-4-methylsulfone, 1 - amino -2,4-dinitrobenzene - 6 - carboxylic acid methyl ester or - / < - methoxyethyl ester, 3,5- dichloroanthranilic acid - propyl ester,
3.5 - Dibromanthranilsäure - β - rnahoxyäthylesier',3.5 - dibromanthranilic acid - β - rnahoxyäthylesier ',
N - Acetyl - ρ - phenylendiamin, 4 - Amino - acetophenon, 4- oder 2-Amino-benzophenon, 2- und 4-Aminodiphenylsulfon, 2-, 3- oder 4-Aminobenzoesäure - methylester, -äthylester, -propylester, -butylester, -isobutylester, -β- methoxy -äthylester, -,·< -äthoxy - äthylester, -methyl - diglykolester, -äthyl-diglykolester, -methyl-triglykolester, -ä t hyl - triglykolc st er, -ß-hydroxyäthylester, -/i-acetoxy-äthylester, -,Hi -hydroxy - äthoxy) - äthylester, -β - hydroxy - pro pylester, 'N - acetyl - ρ - phenylenediamine, 4 - amino - acetophenone, 4- or 2-amino-benzophenone, 2- and 4-aminodiphenylsulfone, 2-, 3- or 4-aminobenzoic acid methyl ester, ethyl ester, propyl ester, butyl ester , -isobutyl ester, -β- methoxy -ethyl ester, -, · <-ethoxy - ethyl ester, -methyl - diglycol ester, -ethyl-diglycol ester, -methyl-triglycol ester, -ä thyl - triglycol ester, -ß-hydroxyethyl ester, - / i-acetoxy-ethyl ester, -, Hi -hydroxy - ethoxy) - ethyl ester, -β - hydroxy - pro pyl ester, '
-γ - hydroxy - propylester, -υ, - hydroxy - butylester, r._r..., , .., -γ - hydroxy - propyl ester, -υ, - hydroxy - butyl ester, r ._ r ...,, ..,
-o) - hydroxy - hexylester, 5 - Nitro - anthranilsäure- 30 wie die Reste der Formern methylester, -isobutylester, -methyl - diglykolester, -0-methoxy-äthylester. -/i-butoxy-äthylester-, -,f-acetoxy - äthylester, 3- oder 4 - Aminophthalsäure-, 5-Amino - isophthalsäure- oder Amino-terephthalsäure - di - methylester, -di - äthylester, -di - propyl- 35 ester, -di-butylester, 3- oder 4-Amino-benzoesäure- -o) - hydroxy - hexyl ester, 5 - nitro - anthranilic acid - 30 like the residues of the formers methyl ester, isobutyl ester, methyl diglycol ester, -0-methoxy-ethyl ester. - / i-butoxy-ethyl ester, -, f-acetoxy - ethyl ester, 3- or 4-aminophthalic acid, 5-amino-isophthalic acid or amino-terephthalic acid - dimethyl ester, -di - ethyl ester, -di - propyl- 35 ester, di-butyl ester, 3- or 4-amino-benzoic acid
amid, -methylamid, -propylamid, -butylamid, -iso-amide, methylamide, propylamide, butylamide, iso-
butylamid, -cyclohexylamid, -ß - äthyl - hexylamid,butylamide, -cyclohexylamide, -ß - ethyl - hexylamide,
-γ - methoxy - propylamid, -7 - äthoxy - propylamid, -γ - methoxy - propylamide, -7 - ethoxy - propylamide,
2-, 3- oder 4-Aminobenzoesäure-dimethylamid, -di-2-, 3- or 4-aminobenzoic acid dimethylamide, -di
äthylamid, -pyrrolidid, -morpholid, N-methyl-N-,i-hy-ethyl amide, pyrrolidide, morpholide, N-methyl-N-, i-hy-
droxy - äthylamid, 5 - Amino - isophthalsäurediamid,droxy - ethylamide, 5 - amino - isophthalic acid diamide,
-bis - γ- methoxy - propylamid, Aminoterephthalsäure--bis - γ- methoxy - propylamide, aminoterephthalic acid-
bis - diäthylamid, 3- oder 4 - Amino - phthalsäure-bis - diethylamide, 3 or 4 - amino phthalic acid
imid, -ß - hydroxy - äthylimid-, -γ - hydroxy - propyi-imide, -ß - hydroxy - ethylimide-, -γ - hydroxy - propyi-
amid, 3 - Amino - 6 - nitro - phthalsäure - β - hydroxy-amide, 3 - amino - 6 - nitro - phthalic acid - β - hydroxy
äthylimid, 2-, 3- oder 4 - Aminobenzosulfonsäure-ethylimide, 2-, 3- or 4-aminobenzenesulfonic acid
dimethylamid, -diäthylamid, -pyrrolidid, -morpholid,dimethylamide, diethylamide, pyrrolidide, morpholide,
Methylsulfonsäure-2'-, -3'- oder ^'-amino-phenyl-Methylsulfonic acid-2'-, -3'- or ^ '- amino-phenyl-
ester, Äthylsulfonsäure - 2'-, -3'- oder -4' - amino-ester, ethyl sulfonic acid - 2'-, -3'- or -4 '- amino-
phenylester, Butylsulfonsäure-2'-, -3'- oder -4'-amino-phenyl ester, butyl sulfonic acid 2'-, -3'- or -4'-amino-
phenylester, Benzolsulfonsäure-2'-, -3'- oder 4'-amino-phenyl ester, benzenesulfonic acid 2'-, -3'- or 4'-amino-
phenylester, 4 - Amino - naphthalsäure - äthylimid,phenyl ester, 4 - amino - naphthalic acid - ethylimide,
-butylimid, -ß - methoxy - äthylimid, -γ - methoxy--butylimide, -ß - methoxy - ethylimide, -γ - methoxy-
propylimid, 4- und 5-Nitro-l-amino-naphthalin,propylimide, 4- and 5-nitro-l-amino-naphthalene,
2 - Amino - anthrachinon, 1 - Amino - 4 - chloranthra-2 - amino - anthraquinone, 1 - amino - 4 - chloranthra-
chinon, 3- oder 4-Aminodiphenylenoxid, 2-Amino-quinone, 3- or 4-aminodiphenylene oxide, 2-amino-
benzthiazol, 2 - Amino - 6 - carbonsäure - methylester-benzthiazole, 2 - amino - 6 - carboxylic acid methyl ester
benzthiazol, 2 - Amino - 6 - methyl - sulfonyl - benz-benzthiazole, 2 - amino - 6 - methyl - sulfonyl - benz-
thiazol, 2 - Amino - 6 - cyanbenzthiazol, 2 - Amino-thiazole, 2 - amino - 6 - cyanobenzothiazole, 2 - amino
f)-nitro-benzthiazol, 5,6- oder 6,7-Dichlor-2-amino-f) -nitro-benzothiazole, 5,6- or 6,7-dichloro-2-amino-
benzthiazol, 4 -Amino- 5 - brom - 7 - nitro -1,2 - benzisothiazol, 3 - Amino - 5 - nitro - 2,1 - benzisothiazol, 3 - Amino - 5 - nitro - 7 - brom - 2,1 - benzisothiazol, 2-Amino-thiazol, 2-Amino-5-nitro-thiazol, 2-Amino-4-methyl-thiazol-5-carbonsäure-äthylester, 2-Amino-4-methyl-5-acetyl-thiazol, 2-Amino-3-cyan-4-methylthiophen - 5 - carbonsäureester, 2 - Phenyl - 5 - amino-CH,-CH2-OH benzthiazole, 4-amino- 5 - bromo - 7 - nitro -1,2 - benzisothiazole, 3 - amino - 5 - nitro - 2,1 - benzisothiazole, 3 - amino - 5 - nitro - 7 - bromo - 2,1 - benzisothiazole, 2-amino-thiazole, 2-amino-5-nitro-thiazole, 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester, 2-amino-4-methyl-5-acetyl-thiazole, 2- Amino-3-cyano-4-methylthiophene-5-carboxylic acid ester, 2-phenyl-5-amino-CH, -CH 2 -OH
-(CH2)3-O -(CH2)*- OH- (CH 2 ) 3 -O - (CH 2 ) * - OH
die Alkoxyalkylreste 0-Methoxyäthyl, y-Methoxypropyl, /3-Äthoxyäthyl, y-Äthoxypropyl oder der Restthe alkoxyalkyl radicals 0-methoxyethyl, y-methoxypropyl, / 3-ethoxyethyl, y-ethoxypropyl or the rest
der Formelthe formula
(CHj)3OC2H4OCH3 (CHj) 3 OC 2 H 4 OCH 3
die Acyloxyalkylreste der Formelnthe acyloxyalkyl radicals of the formulas
CH2—CH2—O—Acyl (CH2)3—O—AcylCH 2 —CH 2 —O — acyl (CH 2 ) 3 —O — acyl
CH2-CH- Ο— Acyl CH3 CH 2 -CH- Ο- acyl CH 3
(CH2)6—Ο—Acyl (CH2)2— Ο—(CH2)2— Ο—Acyl(CH 2 ) 6 - - acyl (CH 2 ) 2 - Ο— (CH 2 ) 2 - Ο - acyl
oderor
(CH2)3-O-(CH2)4-O—Acyl(CH 2 ) 3 -O- (CH 2 ) 4 -O-acyl
wobei Acyl beispielsweisewhere acyl is for example
CO-H CO-CH3 CO-CH2Cl CO-CH2-CO-CH3 CO-CH=CH2 CO-H CO-CH 3 CO-CH 2 Cl CO-CH 2 -CO-CH 3 CO-CH = CH 2
ist.is.
Bei der Herstellung der Farbstoffe der allgemeinen Formel I erfolgt die Diazotierung der Amine wie üblich. Die Kupplung wird ebenfalls wie üblich in wäßrigem Medium, gegebenenfalls unter Zusatz von Lösungsmitteln, bei schwach- bis starksaurer P*eaktion durchgeführtIn the preparation of the dyes of the general formula I, the amines are diazotized as common. The coupling is also carried out as usual in an aqueous medium, optionally with the addition of Solvents, carried out with weak to strongly acidic reaction
Die Herstellung der Kupplungskomponenten der allgemeinen Formel III ist im Prinzip in der deutschen Offenlegungsschrift 2062 717 beschrieben, die Angaben dort gelten bier sinngemäß. <°The preparation of the coupling components of the general formula III is in principle in the German Offenlegungsschrift 2062 717 described, the Information there apply accordingly. <°
Enthalten die erfindungsgemrlßen Farbstoffe der , Formel I eine Estergruppe in den Rest R, so kann die Herstellung der Verbindungen der Formel I im Prinzip nach dem angegebenen Verfahren erfolgen, wenn die entsprechende Estergruppe schon in der Kupplungskomponenie enthalten ist In manchen Fällen ist es aber auch zweckmäßig, den Säurerest (Acyl) in den fertigen Farbstoff der Formel I einzuführen. Dazu eignen sich die freien Säuren, ihre Anhydride, Chloride oder Ester, wobei zweckmäßigerweise inerte Verdünnungs- oder Lösungsmittel, wie Mono-, Dioder Trichlorbenzol, Tetrahydrofuran, Dioxan, Dimethylformamid, N-Methylpyrrolidon oder Pyridin zugesetzt werden.Do the dyes of the invention contain the , Formula I an ester group in the radical R, the preparation of the compounds of the formula I can in principle take place according to the specified procedure if the corresponding ester group is already in the coupling component In some cases it is also useful to use the acid residue (acyl) to be introduced into the finished dye of the formula I. The free acids, their anhydrides, Chlorides or esters, in which case it is expedient to use inert diluents or solvents, such as mono-, di- or Trichlorobenzene, tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone or pyridine can be added.
Bei der Veresterung mit freien Säuren kann es von Vorteil sein, anorganische oder organische Katalysatoren, z. B. HCl-Gas oder p-Toluolsulfonsäure, zuzusetzen und das entstehende Wasser aus dem Reaktionsgemisch durch Verdampfen entweichen zu lassen. Werden Säureanhydride oder -chloride zur Veresterung eingesetzt, so können als Lösungsmittel in speziellen Fällen auch die betreffenden Säuren verwendet werden. So läßt sich die Umsetzung mit Acetanhydrid in Eisessig durchführen. Bei der Verwendung von Säurechloriden als Veresterungsmittel ist es von Vorteil, dem Reaktionsgemisch säurebindende Mittel hinzuzusetzen, z. B. Natriumcarbonat oder -acetat, Magnesiumoxid oder Pyridin. Als Veresterungsmittel seien im einzelnen beispielsweise genannt: Ameisensäure, Essigsäure, Chloressigsäure sowie die Ester, Anhydride oder Chloride dieser Säuren, weiterhin Chlorameisensäureäthylester oder Diketen.When esterifying with free acids, it can be advantageous to use inorganic or organic catalysts, z. B. HCl gas or p-toluenesulfonic acid to be added and to allow the water formed to escape from the reaction mixture by evaporation. Acid anhydrides or chlorides become esterified used, the acids in question can also be used as solvents in special cases will. For example, the reaction with acetic anhydride can be carried out in glacial acetic acid. When using Acid chlorides as esterifying agents, it is advantageous to add acid-binding agents to the reaction mixture to add, e.g. B. sodium carbonate or acetate, magnesium oxide or pyridine. As an esterifying agent are specifically mentioned for example: formic acid, acetic acid, chloroacetic acid and the esters, Anhydrides or chlorides of these acids, also ethyl chloroformate or diketene.
Technisch besonders wertvoll sind Farbstoffe und Farbstoffgemische der allgemeinen Formel I aDyes and dye mixtures of the general formula I a are particularly useful industrially
4545
(la)(la)
Y2 R1- HN Y 2 R 1 - HN
NH-R1 NH-R 1
C2H4OCH3 C 2 H 4 OCH 3
C2H4OC2H5 C 2 H 4 OC 2 H 5
C3H6OCH3 C 3 H 6 OCH 3
C3H6OC2H5 C 3 H 6 OC 2 H 5
CH2CH2OCHOCH 2 CH 2 OCHO
CH2CH2CH2OCHUCH 2 CH 2 CH 2 OCHU
CH2CH2OCOCH3 CH 2 CH 2 OCOCH 3
CH2CH2OCH2Ch2OCHOCH 2 CH 2 OCH 2 Ch 2 OCHO
5555
in der Y Nitro, Cyan, Chlor, Brom, Carbomethoxy, Carboäthoxy, Methylsulfonyl, Äthylsulfonyl, Methyl, Methoxy, Phenylazo, Y1 Wasserstoff, Nitro, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy, Carboäthoxy, Methvlsulfonyl oder Äthylsulfonyl und Y2 Wasserstoff, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy oder Carboäthoxy, ein R1 Phenyl und das andere «j-Hydroxyhexyl, ^-Hydroxyäthyl. /f-Hydroxypropyl, y-Hydroxypropyl oder einen Rest der Formelnin Y nitro, cyano, chlorine, bromine, carbomethoxy, carboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy, phenylazo, Y 1 hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methoxy sulfonyl or ethylsulfonyl and Y 2 hydrogen, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy or carboethoxy, one R 1 phenyl and the other «j-hydroxyhexyl, ^ -hydroxyethyl. / f-hydroxypropyl, γ-hydroxypropyl or a residue of the formulas
-(CH2J2 -O -(CH2J2OH
(CH2)3O(CH2)4OH- (CH 2 J 2 -O - (CH 2 J 2 OH
(CH 2 ) 3 O (CH 2 ) 4 OH
Bei Farbstoffen mit Estergruppen sind solche mit bis 4 C-Atomen im Acylrest bevorzugt.In the case of dyes with ester groups, those with up to 4 carbon atoms in the acyl radical are preferred.
Weiterhin sind besonders wertvoll die entsprechenden Farbstoffe, die als Diazokomponenten gegebenenfalls durch Nitro, Chlor, Brom, Cyan, Methyl, Methylmercapto, ,tf-CarboEEethoxy-aihylmercapto. β - Carboäthoxy - äthylmercapto, Carbomethoxy, Carboäthoxy oder Acetyl substituiertes Benzthiazol, Benzisothiazol, Thiazol, Thiadiazol oder Thiophen enthalten.Furthermore, the corresponding dyestuffs, which are optionally substituted as diazo components by nitro, chlorine, bromine, cyano, methyl, methyl mercapto,, tf-CarboEEethoxy-alkylmercapto, are particularly valuable. β - Carboethoxy - äthylmercapto, Carbomethoxy, Carboethoxy or Acetyl-substituted benzothiazole, benzisothiazole, thiazole, thiadiazole or thiophene contain.
Von den besonders wertvollen Diazokomponenten seien im einzelnen genannt:Some of the particularly valuable diazo components are:
4-Nitro-anilin,4-nitro-aniline,
2-Chlor-4-nitro-anilin,2-chloro-4-nitro-aniline,
2-Brom-4-nitro-anilin,2-bromo-4-nitro-aniline,
2-Cyan-4-nitro-anilin,2-cyano-4-nitro-aniline,
2-Methoxy-4-nitro-anilin,2-methoxy-4-nitro-aniline,
2-Ammo-5-nitro-phenylsulfonsäuredimethylamid, 2-Ammo-5-nitro-phenylsulfonic acid dimethylamide,
2-Amino-5-nitro-phenylsulfonsäure-butylamid. 2-Amino-5-nitro-phenylsulfonsäure-2-Amino-5-nitro-phenylsulfonic acid-butylamide. 2-amino-5-nitro-phenylsulfonic acid
/<-methoxy-äthylamid,
2-Amino-benzonitril,
3-Ch lor-4-amino-benzonitril,
2-Chlor-5-amino-benzonitril,
2-Amino-5-chlor-benzonitril,
2,5-Dichlor-4-amino-benzonitril, 1 -Amino-2,4-dicyanbenzol,
l-Amino-^-dicyan-o-chlor-benzol,
2-Chlor-4-amino-5-nitro-benzonitril, 2-Amino-3-chlor-5-nitro-benzonitril,
2-Amino-3-brom-5-nitro-benzonitril, 2,6-Dicyan-4-nitro-anilin,
2,5-Dichlor-4-nitroanilin,
2,6-Dichlor-4-nitro-anilin,
2,6-Dibrom-4-nitro-aniiin,
2-Chlor-6-brom-4-nitro-anilin,
2,4-Dinitro-anilin,
2,4-Dinitro-6-chlor-anilin,
2,4-Dinitro-6-brom-anilin,
2-Amino-3,5-dinitro-benzonitril, !-Amino^-nitrobenzol^-methylsulfon,
l-Amino-4-nitrobenzol-2-äthylsulfon, 4-Methylsulfonyl-anilin,
l-Amino-2-chlorbenzol-4-methylsulfon. l-Amino-2,6-dibrombenzol-4-methylsulfon,/ <- methoxy-ethylamide,
2-amino-benzonitrile,
3-chloro-4-aminobenzonitrile,
2-chloro-5-aminobenzonitrile,
2-amino-5-chlorobenzonitrile,
2,5-dichloro-4-aminobenzonitrile, 1-amino-2,4-dicyanobenzene,
l-Amino - ^ - dicyan-o-chlorobenzene, 2-chloro-4-amino-5-nitro-benzonitrile, 2-amino-3-chloro-5-nitro-benzonitrile, 2-amino-3-bromo 5-nitro-benzonitrile, 2,6-dicyano-4-nitro-aniline,
2,5-dichloro-4-nitroaniline,
2,6-dichloro-4-nitro-aniline,
2,6-dibromo-4-nitro-aniiine,
2-chloro-6-bromo-4-nitro-aniline, 2,4-dinitro-aniline,
2,4-dinitro-6-chloro-aniline,
2,4-dinitro-6-bromo-aniline,
2-amino-3,5-dinitro-benzonitrile,! -Amino ^ -nitrobenzene ^ -methylsulfone, l-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonyl-aniline,
1-amino-2-chlorobenzene-4-methylsulfone. l-amino-2,6-dibromobenzene-4-methylsulfone,
l-Amino^o-dichlorbenzoM-methylsuifon, 2- und 4-Amino-benzoesäureester, 2-Amino-5-nitro-benzoesäureester, l-Amino-S-chlor-S-nitro-benzoesäureester, 2-Atnino-3,5-dichlor-benzoesäureester, 2-Amino-3,5-dibrom-benzoesäureester, 2-Amino-3,5-dinitro-benzoesäure-methylesterl-Amino ^ o-dichlorobenzoM-methyl sulfone, 2- and 4-amino-benzoic acid ester, 2-amino-5-nitro-benzoic acid ester, l-amino-S-chloro-S-nitro-benzoic acid ester, 2-atnino-3,5-dichloro-benzoic acid ester, 2-amino-3,5-dibromo-benzoic acid ester, 2-Amino-3,5-dinitro-benzoic acid methyl ester
oder -ß-methoxy-äthylester, 2-Atnino-terephthalsäure-diäthylester,
4-Amino-azobenzol,
2,3'-Dimethyl-4-amino-azobenzol, 2',3-Dimcthyl-4-amino-azobenzol,
2,5-Dimethyl-4-amino-azobenzol, 3,5-Dibrom-4-amino-azobenzol,
l-Methyl-S-methoxy^-amino-azobenzol.or -ß-methoxy-ethyl ester, 2-atnino-terephthalic acid diethyl ester, 4-amino-azobenzene,
2,3'-dimethyl-4-amino-azobenzene, 2 ', 3-dimethyl-4-amino-azobenzene, 2,5-dimethyl-4-amino-azobenzene, 3,5-dibromo-4-amino-azobenzene, 1-methyl-S-methoxy ^ -amino-azobenzene.
Von den besonders wertvollen heterocyclischen Diazokomponenten seien erwähnt:Of the particularly valuable heterocyclic diazo components are mentioned:
2-Aminoo-nitro-thiazol,2-aminoo-nitro-thiazole,
2-Aminπ-4-methyl-5-nitro-thiazol, 2-Amino-4-methyl-thiazol-5-carbonsäureäthylester. 2-Aminπ-4-methyl-5-nitro-thiazole, 2-Amino-4-methyl-thiazole-5-carboxylic acid ethyl ester.
2-Amino-j-phenyl-l,3,4-thiadiazol, S-Phenyl-S-amino- I ,2,4-thiadiazol, 3-Methyl-mercapto-5-amino-l,2,4-thiadiazol. S-ß-Carbometnoxy-äthylTnercapto-S-amino-2-Amino-j-phenyl-l, 3,4-thiadiazole, S-phenyl-S-amino-I, 2,4-thiadiazole, 3-methyl-mercapto-5-amino-1,2,4-thiadiazole. S-ß-Carbometnoxy-ethylTnercapto-S-amino-
1,2,4-thiadiazol,
S-zi-Carboathoxy-athylmercaplo-S-amino-1,2,4-thiadiazole,
S-zi-Carboathoxy-ethylmercaplo-S-amino-
1,2,4-thiadiazol.
2-Amino-6-cyan-benzthiazol,
I-Amino-o-carbonsäuremethyl-esterbenzthiazol.
Z-Amino-o-nitro-benzthiazol.
2-Amino-3-cyan-4-methyl-thiophen-1,2,4-thiadiazole.
2-amino-6-cyano-benzothiazole,
I-amino-o-carboxylic acid methyl ester benzothiazole. Z-amino-o-nitro-benzothiazole.
2-amino-3-cyano-4-methyl-thiophene
Niederschlag der wahrscheinlichen FormelPrecipitation of the probable formula
CH3 CNCH 3 CN
NHNH
3-Amir.o-5-r.itro-2,l-benzisothiazol, 3-Amino-5-nitro-7-chlor-2,1-benzisothiazol, 3-Amino-5-nitro-7-brom-2,l-benzisothiazol, 4-Amino-7-nitro-l,2-benzisothiazol, 4-Amino-5-brom-1,2-benzisothiazoL 4-Amino-5-brom-7-nitro-1,2-benzisothiazol, 4-Amino-5-cyan-7-nitro-l .2-benzisothiazol. 4-Amino-5-chlor-7-nitro-1,2-benzisothiazol.3-Amir.o-5-r.itro-2, l-benzisothiazole, 3-Amino-5-nitro-7-chloro-2,1-benzisothiazole, 3-Amino-5-nitro-7-bromo-2, l-benzisothiazole, 4-Amino-7-nitro-1,2-benzisothiazole, 4-amino-5-bromo-1,2-benzisothiazole 4-Amino-5-bromo-7-nitro-1,2-benzisothiazole, 4-Amino-5-cyano-7-nitro-1,2-benzisothiazole. 4-Amino-5-chloro-7-nitro-1,2-benzisothiazole.
Die neuen Farbstoffe sind gelb bis blau und eignen sich zum Färben von Textümaterialien aus Acrylnitrilpolymerisaten, synthetischen Polyamiden, Celluloseestern, wie 2V2- oder Triacetat, und insbesondere von synthetischen linearen Polyestern, wie PoIyäthylenglykolterephthalat oder chemisch analog aufgebauten Polymeren. Man erhält farbstarke Färbungen, die sich durch hervorragende Echtheiten auszeichnen. The new dyes are yellow to blue and are suitable for dyeing textile materials made from acrylonitrile polymers, synthetic polyamides, cellulose esters such as 2V 2 - or triacetate, and in particular synthetic linear polyesters such as polyethylene glycol terephthalate or chemically analogous polymers. Strong dyeings are obtained which are distinguished by excellent fastness properties.
Die Angaben über Teile und Prozente beziehen sich in den folgenden Beispielen auf das Gewicht, wenn es nicht anders vermerkt ist.The data on parts and percentages in the following examples relate to weight, if it is not otherwise noted.
Ein Gemisch aus 187 Teilen 2,6-Dichlor-3-cyan-4-methyl-pyridin, 200 Teilen Isopropanol und 300 Teilen Anilin wird 8 Stunden bei ungefähr 90 bis 100cC gerührt. Dann läßt man erkalten und gießt das Ge- 6s misch unter Rühren in etwa 1500 Teile Wasser. Teile konzentrierte Salzsäure und 200 Teile Eis. Man rührt noch 1 Stunde, saugt den ausgefallenenA mixture of 187 parts of 2,6-dichloro-3-cyano-4-methyl-pyridine, 200 parts of isopropanol and 300 parts of aniline was stirred for 8 hours at about 90 to 100 c C. It is then allowed to cool and the mixture is poured into about 1500 parts of water while stirring. Parts of concentrated hydrochloric acid and 200 parts of ice. The mixture is stirred for a further 1 hour and the precipitated product is sucked off
ab und wäscht ihn mit Wasser neutral. Nach dem Trocknen erhält man ungefähr 240 Teile eines farblosen
Pulvers, das bei 135 bis 1400C schmilzt,
12,2 Teile dieses Pulvers werden mit 40 Teilen }-Hydroxy-propylamin 6 Stunden bei 145 bis 160"1C
gerührt. Dann läßt man erkalten, versetzt das Gemisch mit 100 Teilen Wasser und säuert mit Salzsäure auf
einen pH-Wert von etwa 0 bis 1 an. Man erhält — gegebenenfalls unter Zusatz von etwas Eisessig
oder Dimethylformamid — eine Lösung der Kupplungskomponente der wahrscheinlichen Formeland washes it neutral with water. After drying, about 240 parts of a colorless powder which melts at 135 to 140 ° C. are obtained,
12.2 parts of this powder are mixed with 40 parts} -hydroxy-propylamine 6 hours at 145 to 160 "C for 1, then allowed to cool, the mixture was mixed with 100 parts of water and acidified with hydrochloric acid to a pH of about 0 to 1. A solution of the coupling component of the probable formula is obtained - optionally with the addition of a little glacial acetic acid or dimethylformamide
CH,CH,
CNCN
NH-CH2-CH2-CH2-OHNH-CH 2 -CH 2 -CH 2 -OH
Die Lösung (oder Suspension) dieser Kupplungskomponente wird durch Zugabe von Eis auf O bis 30C abgekühlt und mit einer Diazoniumsalzlösung versetzt, die man wie folgt erhält:The solution (or suspension) of this coupling component is cooled to 0 to 3 ° C. by adding ice and a diazonium salt solution is added, which is obtained as follows:
6,9 Teile p-Nitroanilin werden mit ungefähr 30 Teilen konzentrierter Salzsäure (30%ig) und 80 Teilen Wasser versetzt, dann wird das Gemisch auf 00C abgekühlt und in Anteilen mit 15 Raumteilen 23%iger Natriumnitritlösung versetzt. Man rührt 2 Stunden nach, beseitigt einen gegebenenfalls vorhandenen Überschuß an salpetriger Säure wie üblich und filtriert. About 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water are added to 6.9 parts of p-nitroaniline, then the mixture is cooled to 0 ° C. and 15 parts by volume of 23% sodium nitrite solution are added. The mixture is stirred for a further 2 hours, any excess of nitrous acid which may be present is eliminated as usual and the mixture is filtered.
Das Filtrat wird zum Kupplungsgemisch gegeben und man fügt dann unter Rühren nach und nach so viel Natriumacetat oder Natronlauge zu, daß der pH-Wert des Kupplungsgemisches etwa 2 bis 3 beträgt. Falls das Gemisch schwer rührbar wird, kann Eiswasser zugesetzt werden. Nach beendeter Kupplung wird das Gemisch auf 70 bis 80" C erhitzt, nitriert, mit Wasser gewaschen und getrocknet. Man erhält ungefähr 20 Teile eines rotbraunen Pulvers der wahrscheinlichen FormelThe filtrate is added to the coupling mixture and then gradually added with stirring a lot of sodium acetate or caustic soda so that the pH of the coupling mixture is about 2 to 3 amounts to. If the mixture becomes difficult to stir, ice water can be added. After finished Coupling, the mixture is heated to 70 to 80 ° C., nitrated, washed with water and dried gets about 20 parts of a red-brown powder of the likely formula
CH, CNCH, CN
NH-CH1-CH2-CH1-OHNH-CH 1 -CH 2 -CH 1 -OH
das sich in Dimethylformamid mit roter Farbe löst und Polyäthylenterephthalgewebe in kräftigen, klaren scharlachroten Tönen mit hervorragenden Echtheiten färbt.which dissolves in dimethylformamide with a red color and polyethylene terephthalmic fabric in strong, clear dyes scarlet shades with excellent fastness properties.
Analog der beschriebenen Verfahrensweise können die folgenden durch Diazo- und Kupplungskomponente charakterisierten Farbstoffe erhalten werden. The following dyes characterized by diazo and coupling components can be obtained analogously to the procedure described.
409522/404409522/404
Tabelle 1 KupplungskomponenteTable 1 coupling component
CH3 CNCH 3 CN
1010
NHR2 NHR 2
Nr.example
No.
3
42
3
4th
^^NHjCOOCH 3
^^ NHj
—CH2-CH2-OH
—CH,- CHj—CHj- OH-CH 2 -CHj-CH 2 -O-CH 3
-CH 2 -CH 2 -OH
-CH, -CHj-CHj-OH
Goldgelb
RotstichiggelbRolstichig yellow
Golden yellow
Reddish yellow
9
108th
9
10
<J>-NHj CN
<J> -NHj
—CH2-CHj—OH
-CH2-CH2-CH2-OHH
-CH 2 -CHj-OH
-CH 2 -CH 2 -CH 2 -OH
Rotstichiggelb
RotstichiggelbReddish yellow
Reddish yellow
Reddish yellow
14
1513th
14th
15th
Cl-^/j^NHjCN
Cl - ^ / j ^ NHj
—CHj—CHj— OH
—CH,-CH2- CH2-OH-H
—CHj — CHj — OH
-CH, -CH 2 -CH 2 -OH
Goldgelb
GoldgelbReddish yellow
Golden yellow
Golden yellow
19
2018th
19th
20th
Br-Zj^-NH2 CN
Br-Zj ^ -NH 2
-CH2-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
Goldgelb
GoldgelbGolden yellow
Golden yellow
Golden yellow
I-CH 2 -CH-OH
I.
Fortsetzungcontinuation
Nr.example
No.
-CH2-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
2524
25th
ScharlachScarlet fever
Scarlet fever
Br I.
Br
scharlachBrownish tinge
Scarlet fever
\
CH3 —CH, -CH
\
CH 3
scharlachRed orange
Scarlet fever
OO 1414th
Fortsetzungcontinuation
Nr.example
No.
Orangeorange
orange
6463
64
-CH2-CHj-O-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CHj -O-CH 2 -CH 2 -OH
ν^Γΐ2 V-O 7 ν_Γ12 vJ Γιν ^ Γΐ2 V-O 7 ν_Γ12 vJ Γι
NI.
N
titi
89 9089 90
1515th
Fortsetzungcontinuation
Nr.example
No.
8382
83
CH3-N- S-^ V"NH2
OI Ii / Γ \ χ
CH 3 -N- S- ^ V "NH 2
O
—CH2-CH2-O—CHj—CHj—OH-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CHj-CHj-OH
Orangeorange
orange
OH-CHj-CH 2 -CH 2 -OH
OH
CH2-CH2-O-CH3 CH2 CH 2 -CH 2 -O-CH 3 CH 2
V=OV = O
>— NH,> - NH,
CH2-CH2-OH
-CH2-CH2-CH2-OH
-CH2-CH2-O-CH2-CH2-OHCH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
91 CH3-O-CH2-CH2-N-C-^f VnH; 91 CH 3 -O-CH 2 -CH 2 -NC- ^ f VnH ;
92 j H 92 j H
93 9493 94
HH
Nil,Nile,
-CHj-CH,—OH
CH,- CH- -CH,-OH-CHj-CH, -OH
CH, - CH- -CH, -OH
JH- dl· OllJH- dl · Oll
, !,- CU, CH, OH,!, - CU, CH, OH
Goldgelborange Go'dgelborange GoldgelborangeGolden yellow orange golden yellow orange
Orange i O ran ccOrange i O ran cc
.orange >range.orange> range
Tabelle 2 K upplungskomponenteTable 2 coupling component
CH3 CN
/>-NH—R1 CH 3 CN
/> - NH-R 1
YnYn
NH-/ SNH- / S
/0/ 0
Nr.example
No.
scharlachBrownish tinge
Scarlet fever
scharlachBrownish tinge
Scarlet fever
Cl-/ V-NHj I.
Cl- / V-NHj
Fortsetzung Continuation
Nr.No.
114
115113
114
115
NCH 2 -CH 2 -OH
N
-CH2-CH2-CH2-OH
-CH2-CH2-CH2-O-CH3 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -O-CH 3
Orange
Orangeorange
orange
orange
24,4 Teile des Umsetzungsproduktes von Anilin mit 2,6-Dichlor-3-cyan-4-methylpyridin (s. Beispiel 1) werden mit 80 Teilen j^Methoxypropylamin 8 Slunden unter Druck bei 140 bis 160° C gerührt, dann läßt man erkalten, setzt 8 Teile 50%ige Natronlauge zu und destilliert überschüssiges y-Methoxy-propylamin und Wasser ab. Der Rückstand wird mit 100 Teilen 85%iger Schwefelsäure 5 Stunden bei 1000C behandelt. Nach dem Erkalten gießt man das Gemisch in eine Mischung von etwa 500 Teilen Wasser, 600 Teilen Eis und 100 Teilen 50%iger Natronlauge. Zu dem auf O0C abgekühlten Gemisch, das die Kupplungskomponente der wahrscheinlichen Formel24.4 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) are stirred with 80 parts of methoxypropylamine for 8 hours under pressure at 140 to 160 ° C., then left cool, 8 parts of 50% sodium hydroxide solution are added and excess γ-methoxypropylamine and water are distilled off. The residue is treated with 100 parts of 85% sulfuric acid at 100 ° C. for 5 hours. After cooling, the mixture is poured into a mixture of about 500 parts of water, 600 parts of ice and 100 parts of 50% sodium hydroxide solution. To the mixture cooled to O 0 C, which is the coupling component of the probable formula
CH3 CONH,CH 3 CONH,
(Vnh(Vnh
rN r N
NH-CH2-CH2-CH2-O-CH3 NH-CH 2 -CH 2 -CH 2 -O-CH 3
enthält, gibt man dann in Anteilen eine Lösung von diazotiertem 3-Amino-5-nitro-2,l-benzisothiazol, die wie folgt hergestellt wird:contains, one is then in proportions a solution of diazotized 3-amino-5-nitro-2, l-benzisothiazole, the is made as follows:
19,5 Teile 3-Amino-5-nitro-2,l-benzisothiazol werden unter Rühren bei 15 bis 2b°C in Portionen zu ungefähr 75 bis 85 Teilen 96%iger Schwefelsäure gegeben und auf 0 bis 4° C abgekühlt. Dann tropft man bei dieser Temperatur 32,5 Teile 23%ige Nitrosylschwefelsäure zu. Die Diazotierung ist nach etwa 4stündigem Rühren bei 0 bis 5°C beendet. Nach dem Versetzten des Kupplungsgemisches mit der Diazoniumlösung wird der pH-Wert des Gemisches durch Zugabe eines säurebindenden Mittels wie Natriumacetat (oder Natronlauge) auf ungefähr 1,5 bis 2,5 erhöht. Um eine gute Rührung bei 0 bis 5° C zu erreichen, setzt man dabei zweckmäßigerweise Eis und Eiswasser zu. Nach beendeter Kupplung wird das Gemisch auf 60 bis 80° C erwärmt, der ausgefallene Farbstoff abgesaugt und mit heißem Wasser gewaschen. Nach dem Trocknen erhält man etwa 40 Teile eines schwarzen Farbstoffpulvers der wahrscheinlichen Formel19.5 parts of 3-amino-5-nitro-2, l-benzisothiazole become with stirring at 15 to 2 ° C. in portions of approximately 75 to 85 parts of 96% strength sulfuric acid given and cooled to 0 to 4 ° C. 32.5 parts of 23% strength nitrosylsulfuric acid are then added dropwise at this temperature to. The diazotization is complete after about 4 hours of stirring at 0 to 5 ° C. After this Adding the diazonium solution to the coupling mixture increases the pH of the mixture Add an acid binding agent such as sodium acetate (or caustic soda) to about 1.5 to 2.5 elevated. In order to achieve good stirring at 0 to 5 ° C., it is expedient to use ice and ice water too. After the coupling has ended, the mixture is heated to 60 to 80 ° C., the precipitated one Sucked off dye and washed with hot water. After drying you get about 40 parts of a black dye powder of the likely formula
122 Teile des Umsetzungsproduktes von Anilin mit 2,6-Dichlor-3-cyan-4-methylpyridin (s. Beispiel 1) werden mit 150 feilen N-Methylpyrrolidon und ungefähr JOOO Teilen 25%igem Ammoniak 15 Stunden bei 180° C im Autoklav behandelt. Nach dem Erkalten wird das ausgefallene Produkt der wahrscheinlichen Formel122 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) be with 150 files N-methylpyrrolidone and approximately JOOO parts of 25% ammonia treated in an autoclave at 180 ° C. for 15 hours. After cooling down becomes the failed product of the probable formula
CNCN
abfiltriert, mit Wasser gewaschen und getrocknet.filtered off, washed with water and dried.
Man erhält etwa 108 Teile eines farblosen Produktes.About 108 parts of a colorless product are obtained.
22,4 Teile dieses Produktes werden in ungefähr22.4 parts of this product will be roughly
100 Teilen Eisessig gelöst, dann durch Zugabe vonDissolve 100 parts of glacial acetic acid, then by adding
Eis auf 0 bis 20C abgekühlt und mit etwas Amido-Ice cooled to 0 to 2 0 C and with a little amido
sulfonsäure versetzt. Zu diesem Kupplungsgemisch gibt man bei 00C in Anteilen eine Lösung von diazotiertem 2-Amino-5-nitro-benzonitril, die wie folgt hergestellt wird:sulfonic acid added. For this coupling mixture at 0 0 C is added in portions a solution of diazotized 2-amino-5-nitro-benzonitrile, which is prepared as follows:
16,3 Teile 2-Amino-5-nitro-benzonitril werden in Anteilen zu einem auf O0C abgekühlten Gemisch von ungefähr 90 Teilen 96%iger Schwefelsäure und16.3 parts of 2-amino-5-nitro-benzonitrile are added in proportions to a mixture of approximately 90 parts of 96% strength sulfuric acid and cooled to 0 ° C.
32,5 Teilen 23%iger Nitrosylschwefelsäure gegeben,32.5 parts of 23% nitrosylsulfuric acid added,
Nach 4- bis 5stündigem Rühren bei 0 bis 4° C ist die Diazoticrung beendet.After stirring for 4 to 5 hours at 0 to 4 ° C, the Diazotization ended.
Um die Kupplung rasch und vollständig durchzu-In order to quickly and completely pass through the coupling
führen, wird das Kupplungsgemisch — das mit Eis und Eiswasser verdünnt werden kann — bei 0 bis 5°C durch Zugabe von Natriumacetatlösung auf der pH-Wert von etwa 2,5 eingestellt. Nach beendetei Kupplung wird das Gemisch auf etwa 8O0C erhitztlead, the coupling mixture - which can be diluted with ice and ice water - is adjusted to a pH of about 2.5 at 0 to 5 ° C. by adding sodium acetate solution. After beendetei coupling, the mixture is heated to about 8O 0 C
der ausgefallene Farbstoff der wahrscheinlichen Formel the fancy dye of the likely formula
O7NO 7 N
CH3 CH 3
CNCN
N=NN = N
NHNH
NO,NO,
NH,NH,
CH, CONH2 CH, CONH 2
N=NN = N
NHNH
-N
I
NH-CH2 -N
I.
NH-CH 2
CH2-CH2-O-CH3 CH 2 -CH 2 -O-CH 3
das sich in Dimethylformamid mit blauer Farbe lösl und Polyäthylenterephthalatgewebe in grünstichigblauen Tönen mit sehr guten Echtheilen färbl.which is soluble in dimethylformamide with blue color and polyethylene terephthalate fabric in greenish blue tones with very good real healings.
abfiltriert und mit heißem Wasser gewaschen. Mar erhält ungefähr 38 Teile eines dunkelbraunen Pulvers das sich in Dimethylformamid mit roter Farbe lösi und Polyäthylenterephthalatgewebe mit vorzüglicher Echtheiten in kräftigen rosa bis roten Tönen färbt.filtered off and washed with hot water. Mar receives about 38 parts of a dark brown powder which dissolves in dimethylformamide with red color and polyethylene terephthalate fabric with excellent Dyes fastness properties in strong pink to red tones.
Analog zu der in den Beispielen 1, 116 und II/ beschriebenen Arbeitsweise lassen sich die in den folgenden Tabellen durch Diazo- und Kupplungskomponente charakterisierten Farbstoffe herstellen.Analogously to the procedure described in Examples 1, 116 and II /, the in the The following tables produce dyes characterized by diazo and coupling components.
ΪΙΪΙ
KupplungskomponenteCoupling component
NH-R,NH-R,
Nr.example
No.
CH3 I.
CH 3
ιBr
ι
-CH2-CH-OHCH 2 CH 2 CH 2 OH
-CH 2 -CH-OH
134133
134
Rubinruby
ruby
Forlsclziin«Forlsclziin "
Nr.Br-Kpiel
No.
Ι^.Γΐ2 ν- ri 2 V_,ri2— vJriΙ ^ .Γΐ2 ν- ri 2 V_, ri2— vJri
-CH2-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
156155
156
DunkelrotDark red
Dark red
BrBr
Fortsetzungcontinuation
Nr.icigame
No.
2727
Fortsetzungcontinuation
(C(C.
2828
Beispiel Nr.Example no.
190 191 192190 191 192
193 194 195 196193 194 195 196
DiazokomponenteDiazo component
NH2 NH 2
CH 2 CH 2 "CH2*~~OHCH 2 CH 2 "CH2 * ~~ OH
-CH2-CH-OH-CH 2 -CH-OH
CH3 CH 3
-CH2-CH2-O-CH2-CH2-OH
-(CHj)6-OH
-(CHj)3-O-(CHj)4-OH
-CH2-CHj-CHj-O-C-CH3 -CH 2 -CH 2 -O-CH 2 -CH 2 -OH
- (CHj) 6 -OH
- (CHj) 3 -O- (CHj) 4 -OH
-CH 2 -CHj-CHj-OC-CH 3
Farbtonhue
RotstichigblaReddish blue
MarineblauNavy blue
MarineblauNavy blue
Marineblau Marineblau Marineblau RotstichigblaNavy blue Navy blue Navy blue Reddish blue
197197
NH2 NH 2
Br(Cl) —CHj-CH2- O—CHj—CHj— OHBr (Cl) -CHJ-CH 2 - O-CHj-OH CHj-
Blaublue
(Blau)(Blue)
198 199198 199
O NH2 O NH 2
-CHj—CH2- CH2- OH-CHJ-CH 2 - CH 2 - OH
-CHj— CHj— O—CHj—CHj-OH-CHj-CHj-O-CHj-CHj-OH
Rotbraun RotbraunRed-brown red-brown
200 201200 201
SO2C6H5
-CH2-CH2-CH2- OH
-CH2-CH2-O-CHj-CHj-OHSO 2 C 6 H 5 -CH 2 -CH 2 -CH 2 - OH
-CH 2 -CH 2 -O-CHj -CHj-OH
Goldgelb GoldgelbGolden yellow golden yellow
202 203202 203
204 205 206204 205 206
207207
-CHj-CH2-O-CH2-CH2-OH
-(CHj)3-O-H-CHj-CH 2 -O-CH 2 -CH 2 -OH
- (CHj) 3 -OH
Goldgelb GoldgelbGolden yellow golden yellow
— CHj—CHj—OH- CHj-CHj-OH
—CH2-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH2-CH-OH-CH 2 -CH-OH
OH
—CH2-CHj-O-CHj-CH2-OHOH
-CH 2 -CHj-O-CHj -CH 2 -OH
Violett
Violett
Violettviolet
violet
violet
Violettviolet
Fortsetzungcontinuation
Nr.example
No.
Br I.
Br
LrIi LlT.2 ^* ^-·*~*2 "1_^Γΐ2*" KJ Γί / "■ τι f ^ lj Γ \ i ^ U (~ * \ JC \ U
LrIi LlT.2 ^ * ^ - · * ~ * 2 "1_ ^ Γΐ2 *" KJ Γί
1./.-1I1./.- 1 I.
3131
Fortsetzungcontinuation
DiazokomponenteDiazo component
225 226225 226
227227
228 229 230 231228 229 230 231
CNCN
O2N-<ζ\O 2 N- <ζ \
S jfr S jfr
N 'N '
SO2C2HSO 2 C 2 H
2C2H5 2 C 2 H 5
O,NO, N
-N-N
-NH, -CH2-CH2-CH2-OH
-CH1-CH2-O-CH2-CH2-OH-NH, -CH 2 -CH 2 -CH 2 -OH
-CH 1 -CH 2 -O-CH 2 -CH 2 -OH
CH2-CH2-OHCH 2 -CH 2 -OH
CH2-CH2-CH2-OH
-CH2-CH2-O-CH2-CH2-OHCH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
Farbtonhue
Violett
Violettviolet
violet
Rubinruby
Rotorange Scharlach Scharlach ScharlachRed-orange scarlet scarlet scarlet fever
232 233 234232 233 234
235 236235 236
237 238 239237 238 239
IiIi
CH3O-C-C2H4- S —[ι NCH 3 OCC 2 H 4 - S - [ι N
L-NH- -CH2-CH2-OH L -NH- -CH 2 -CH 2 -OH
-CH2-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH2-CH-OH-CH 2 -CH-OH
CH3 CH 3
-CH2-CH2-O-CH2-CH2-OH
-H-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-H
240 241 242 243240 241 242 243
244 245 246244 245 246
JL-J L -
NH,NH,
CH1-O-CCH 1 -OC
-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH2-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH2-CH2-OH
-CH2-CH2-CH2-OH
-CH2-CH2-O-CH2-CH2-OH
-CH2-CH-OH-CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH 2 -CH-OH
CH3 CH 3
CH3 CH 3
CNCN
C2H5-O-CC 2 H 5 -OC
il ο CH2-CH2-OH
-CH2-CH2-CH2-OH
CH; -CH2-O-CH2-CH2-OH il ο CH 2 -CH 2 -OH
-CH 2 -CH 2 -CH 2 -OH
CH; -CH 2 -O-CH 2 -CH 2 -OH
Scharlach Scharlach Sche-'achScarlet Fever Scarlet She-'ach
Scharlach RotorangeScarlet red-orange
Violett
Violelt
Violettviolet
Violelt
violet
Blaustichigrot Rotviolelt Rotviolett RotvioleliBluish red red-violet red-violet red-violet
Rolviolelt Rotviolelt RotviolettRolviolelt Red-violet Red-violet
409 522/404409 522/404
Fortsetzung continuation
(S(P
Nr.example
No.
CNι
CN
\ /
SO 2 N - '■! / —NH,
\ /
S.
Kupplungskomponente CH3 CNCoupling component CH 3 CN
NH-/NH- /
Nr.example
No.
Rot
RotRed
Red
Red
255
256254
255
256
-CH2-CHj-CH2-OH
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH 2 -CHj-CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
Rot
Rosa
Dunkclrot
Rosa
Rosa
Dunkelroipink
Red
pink
Dark red
pink
pink
Darkroi
258
259
260
261
262
263257
258
259
260
261
262
263
OjN-/j^NHj ·CN
OjN- / j ^ NHj
-CH2-CH2-OH
-CH2-CH2-O-COCH3
-CH2-CH2-CH2- OH
-CH2-CH2-O-CH2-CH2-OH
-CH2-CH2-O-CH2-Ch2OCHO
-(CH2),,-OH LJ
-CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-COCH 3
-CH 2 -CH 2 -CH 2 - OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -Ch 2 OCHO
- (CH 2 ) ,, - OH
Fortsetzungcontinuation
'9'9 3636
-CH2-CH2-CH2-OH -CH1-CH1-O-CH2-CH1-OH-CH 2 -CH 2 -CH 2 -OH -CH 1 -CH 1 -O-CH 2 -CH 1 -OH
Rubin Rubin Rubin RubinRuby ruby ruby ruby
— H- H
-CH2-CH2-OH -CH2-CH2-CH2-OH —CH,- CH-OH-CH 2 -CH 2 -OH -CH 2 -CH 2 -CH 2 -OH -CH, -CH-OH
-CH1-CH1-O-CH2-CH2-OH-CH 1 -CH 1 -O-CH 2 -CH 2 -OH
Rubin Rubin Rubin RubinRuby ruby ruby ruby
CH2-CH2-OH CH2-CH2-CH2-OHCH 2 -CH 2 -OH CH 2 -CH 2 -CH 2 -OH
CH2-CH2-O-CH2-CH2-OHCH 2 -CH 2 -O-CH 2 -CH 2 -OH
■(CH,)3—O—(CH2U—OH■ (CH,) 3 -O- (CH 2 U-OH
-CH1-CH2-CH2-OH-CH 1 -CH 2 -CH 2 -OH
CH5-CH2-CH2-OH -CH2-O-CH2-CH2-OHCH 5 -CH 2 -CH 2 -OH -CH 2 -O-CH 2 -CH 2 -OH
-CH5-CH2-CH2-OH-CH 5 -CH 2 -CH 2 -OH
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
Marineblau MarineblauNavy blue navy blue
-CH2-CH2-OH-CH 2 -CH 2 -OH
2
CH2-CH2-O-CH2-CH2-OH 2
CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-O-CH2-CH2-OH-O-CH 2 -CH 2 -OH
-CH1-CH2 -CH 1 -CH 2
3737
Fortsetzungcontinuation
IoIo
3838
R1 R 1
FarbionColor ion
-CH1-CH2-O-CH2-CH2-OH Blau -CH 1 -CH 2 -O-CH 2 -CH 2 -OH blue
-CH2-CH2-OH-CH 2 -CH 2 -OH
-CH1-CH2-CH2-OH-CH 1 -CH 2 -CH 2 -OH
-CH-CH2-O-CH-CH2-OH-CH-CH 2 -O-CH-CH 2 -OH
-CH2-CH2-CH2-OH
-CH2-CH2- 0-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 - O-CH 2 -CH 2 -OH
-CH1-CH2-CH2-OH
-CH2-CH2-O-CH2-CH2-OH-CH 1 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH2-CH2-CH2-OH
-CH1-CH7-O-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH 1 -CH 7 -O-CH 2 -CH 2 -OH
Kupplungskomponente
CH3 CONH2 Coupling component
CH 3 CONH 2
Vn V n
NH-R2 NH-R 2
Nr.No.
293 294 295 296293 294 295 296
Ο,Ν—<rΟ, Ν— <r
NH, CH2-CH2-O-COCH,
CH2-CH2-CH2-O-COCH3
CH2-CH2-CH2-OH
CH2-CH2-O-CH3 NH, CH 2 -CH 2 -O-COCH,
CH 2 -CH 2 -CH 2 -O-COCH 3
CH 2 -CH 2 -CH 2 -OH
CH 2 -CH 2 -O-CH 3
Dunkelrot Dunkelrot DunkelrotDark red Dark red Dark red
Violett ViolettViolet violet
Violett ViolettViolet violet
Rot RotRed Red
Farbtonhue
Rot Rot Rot Rot Red red red red
Beispiel Nr.Example no.
297 298 299 300 30! 302297 298 299 300 30! 302
Nr.No.
319 320319 320
3939
Fortsetzungcontinuation
4040
DiazokomponenteDiazo component
CNCN
Ο,ΝΟ, Ν
NH,NH,
DiazokomponenteDiazo component
ClCl
Ο,ΝΟ, Ν
// ν // ν
NH, -CH2-CH2-OCOCH3 NH, -CH 2 -CH 2 -OCOCH 3
-CH2-CH2-CH2-OCOCh3 -CH 2 -CH 2 -CH 2 -OCOCh 3
—CIi2 CH2 C-H. 2 OH- Cli2 CH2 C-H. 2 OH
-CH2-CH2-O-CH2-CH2-OCOCh3 -CH 2 -CH 2 -O-CH 2 -CH 2 -OCOCh 3
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH2-CH2-O-CH3 -CH 2 -CH 2 -O-CH 3
-CH2-CH2-CH2-OCOCh3
-CH2-CH2-CH2-OH
-CH2-CH2-O -CH2-CH2-OCOCH3
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OCOCh 3
-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O -CH 2 -CH 2 -OCOCH 3
-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
CH2 CH3
-CH2-CH2-CH2-O-CH3 CH 2 CH 3
-CH 2 -CH 2 -CH 2 -O-CH 3
Ο—COCH2-COCH3
-OCOCH3
-CH2-O-COCH3
-CH2-OH
-Ο—CH3
-CH2-O-C2H5
-Ο—CH2-CH2-OCHO
-0-CH2-CH2-OH
-0-CH2-CH2-O-COCH3 Ο — COCH 2 -COCH 3
-OCOCH 3
-CH 2 -O-COCH 3
-CH 2 -OH
-Ο — CH 3
-CH 2 -OC 2 H 5
-Ο — CH 2 -CH 2 -OCHO
-0-CH 2 -CH 2 -OH
-0-CH 2 -CH 2 -O-COCH 3
-CH2-Ch2-O-CH2-CH2-O-COCH3 -CH 2 -Ch 2 -O-CH 2 -CH 2 -O-COCH 3
Farbtonhue
Blaustichigrot Blaustichigrot Blaustichigrot Blaustichigrot Blaustichigrot BlaustichigrolBluish red bluish red bluish red bluish red bluish red Bluish tint
Violett
Violett
Violett
Violett
Violett
Violettviolet
violet
violet
violet
violet
violet
Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau GrünstichigblauGreenish blue Greenish blue Greenish blue Greenish blue Greenish blue Greenish blue Greenish blue Greenish blue Greenish blue
GrünstichigblaiGreenish blue
Kupplungskomponente
CH3 CONH2 Coupling component
CH 3 CONH 2
<^V-NH—R1 <^ V-NH-R 1
VnVn
-CH2-Ch2-CH2-OCOCH3
-CH2-CH2-CH2-OH-CH 2 -Ch 2 -CH 2 -OCOCH 3
-CH 2 -CH 2 -CH 2 -OH
FarbionColor ion
Rot
RotRed
Red
409522409522
321 322 323 324321 322 323 324
4141
Fortsetzungcontinuation
DiazokomponenteDiazo component
CNCN
O2NO 2 N
// ν // ν
NH, -CH2-Ch2-CH2-OCOCH3
-CH2-CH2-CH2-OH
-CH2-CH2-O-Ch2-CH2-OCOCH3
-CH2-CH2-O-Ch2-CH2-OCHONH, -CH 2 -Ch 2 -CH 2 -OCOCH 3
-CH 2 -CH 2 -CH 2 -OH
-CH 2 -CH 2 -O-Ch 2 -CH 2 -OCOCH 3
-CH 2 -CH 2 -O-Ch 2 -CH 2 -OCHO
FarbionColor ion
Blaustichigrot
Blaustichigrot
Blauslichigrot
BlaustichigrotBluish red
Bluish red
Bluish red
Bluish red
325 326 327325 326 327
328 329 330 331 332 333328 329 330 331 332 333
O2NO 2 N
NH, -CH2-CH2-CH2-O-COCH3 NH, -CH 2 -CH 2 -CH 2 -O-COCH 3
-CH3-Ch2-O-CH2-CH2-OCHO-CH 3 -Ch 2 -O-CH 2 -CH 2 -OCHO
-CH2-CH2-O-CH2-Ch2-O-COCH3 -CH 2 -CH 2 -O-CH 2 -Ch 2 -O-COCH 3
Violett
Violett
Violettviolet
violet
violet
-CH2-CH2-CH2-O-COCH3 -CH 2 -CH 2 -CH 2 -O-COCH 3
-CH2-CH2-CH2-OCOCH2-COCh3 -CH 2 -CH 2 -CH 2 -OCOCH 2 -COCh 3
-CH2-CH2-CH2-OH-CH 2 -CH 2 -CH 2 -OH
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
-CH2-Ch2-O-CH2-CH2-OCHO-CH 2 -Ch 2 -O-CH 2 -CH 2 -OCHO
-CH2-CH2-O-CH2-CH2-OCOCh3 -CH 2 -CH 2 -O-CH 2 -CH 2 -OCOCh 3
Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau Grünstichigblau GrünstichigblauGreenish blue Greenish blue Greenish blue Greenish blue Greenish blue Greenish blue
334 335 336 337334 335 336 337
O2NO 2 N
NH, -CH2-CH2-O-CH2-CH2- OCH O
-CH2-CH2-O-CH2-Ch2-O-COCH3
-CH2- CH2- 0-CH2-CH2- OH
-(CH2I3-O-(CH2V- OHNH, -CH 2 -CH 2 -O-CH 2 -CH 2 - OCH O
-CH 2 -CH 2 -O-CH 2 -Ch 2 -O-COCH 3
-CH 2 - CH 2 - O-CH 2 -CH 2 - OH
- (CH 2 I 3 -O- (CH 2 V- OH
Grünstichigblau Grünstichigblau Grünstichigblau GrünstichigblauGreenish blue Greenish blue Greenish blue Greenish blue
338 339338 339
NH, -CH2-CH2-O-CH2-CH2-OCOCh3
—CH2 CH2 CH2 O CH3 NH, -CH 2 -CH 2 -O-CH 2 -CH 2 -OCOCh 3
-CH 2 CH 2 CH 2 O CH 3
Grünstichigblau GrünstichigblauGreenish blue Greenish blue
Analog können die folgenden Farbstoffe hergestellt werden:The following dyes can be prepared analogously:
Nr.No.
340340
341341
N=N-N = N-
NH-NH-
RotRed
NH-CH2-CH2-O-CH2-Ch2-OHNH-CH 2 -CH 2 -O-CH 2 -Ch 2 -OH
CH3 CNCH 3 CN
CH1OCH2CH2-NCH 1 OCH 2 CH 2 -N
BlaustichigrotBluish red
NH-CH2-CH2-O-Ch2-CH2-OHNH-CH 2 -CH 2 -O-Ch 2 -CH 2 -OH
4343
Fortsetzungcontinuation
Beispiel Nr.Example no.
342342
Beispiel 11 Teile des Farbstoffs der FormelExample 11 parts of the dye of the formula
0 ran nc0 ran nc
N H-^ % ScharlachN H- ^ % scarlet fever
NH-CH2-CH2-O-Ch2-CH1-OHNH-CH 2 -CH 2 -O-Ch 2 -CH 1 -OH
ϊο filtriert den ausgefallenen Niederschlag der Formel CN CH1 CNϊο filtered the precipitate of the formula CN CH 1 CN
Ο,Ν—^ \—κι=>Ο, Ν— ^ \ —κι =>
NH-CH2-CH2-OH (Beispiel 118)NH-CH 2 -CH 2 -OH (Example 118)
NH-CH2-CH2-O-C-CNH-CH 2 -CH 2 -OCC
ab, wäscht ihn mit Wasser und trocknet. Man crhiil ungefähr 11 Teile eines dunkelbraunen Pulvers, da;wash it off with water and dry it. Man crhiil about 11 parts of a dark brown powder, da;
werden mit 100 Raumteilen Ameisensäure 4 Stunden sich in Dimethylformamid mit roter Farbe löst um unter Rückflußkühlung erhitzt. Nach dem Erkalten Polyäthylcnterephthalatgewcbein rosa bis roten Tönet setzt man unter Rühren ungefähr 100 Teile Wasser zu, 35 mit hervorragenden Echtheiten färbt.100 parts by volume of formic acid are dissolved in dimethylformamide with a red color for 4 hours heated to reflux. After cooling, polyethylene terephthalate fabric pink to red tones about 100 parts of water are added with stirring, dyeing with excellent fastness properties.
Claims (1)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722211663 DE2211663C3 (en) | 1972-03-10 | 1972-03-10 | Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations |
| CH321773A CH596263A5 (en) | 1972-03-10 | 1973-03-05 | |
| IN502/CAL/73A IN139039B (en) | 1972-03-10 | 1973-03-07 | |
| CS163973A CS178421B2 (en) | 1972-03-10 | 1973-03-07 | |
| US05/338,859 US4042578A (en) | 1972-03-10 | 1973-03-07 | Azo dyes having 2,6-diaminopyridine derivatives as coupling components |
| DD169311A DD106192A5 (en) | 1972-03-10 | 1973-03-08 | |
| NL7303378A NL7303378A (en) | 1972-03-10 | 1973-03-09 | |
| GB1140873A GB1422650A (en) | 1972-03-10 | 1973-03-09 | Azo dyes having 2,6-diaminopyridine derivatives as coupling components |
| FR7308567A FR2187857B1 (en) | 1972-03-10 | 1973-03-09 | |
| SU1891749A SU521848A3 (en) | 1972-03-10 | 1973-03-09 | The method of obtaining 2,6-diaminopyridine azo dye |
| BE128597A BE796542A (en) | 1972-03-10 | 1973-03-09 | AZOIC DYES OBTAINED FROM COPULANTS CONSISTING OF 2,6-DIAMINOPYRIDINE DERIVATIVES |
| IT48707/73A IT979789B (en) | 1972-03-10 | 1973-03-09 | AZOCOLORANTS WITH 2, 6 DIAMMINOPYRIDINE DERIVATIVES AS COPULATION COMPONENTS |
| JP48027651A JPS6139347B2 (en) | 1972-03-10 | 1973-03-10 | |
| US05/711,863 USRE29640E (en) | 1970-12-19 | 1976-08-05 | Certain substituted 2,6-diamino-4-methyl-nicotinitriles the corresponding nicotinamides and derivatives thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722211663 DE2211663C3 (en) | 1972-03-10 | 1972-03-10 | Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2211663A1 DE2211663A1 (en) | 1973-09-20 |
| DE2211663B2 true DE2211663B2 (en) | 1974-05-30 |
| DE2211663C3 DE2211663C3 (en) | 1975-01-16 |
Family
ID=5838560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722211663 Expired DE2211663C3 (en) | 1970-12-19 | 1972-03-10 | Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE796542A (en) |
| DE (1) | DE2211663C3 (en) |
| IN (1) | IN139039B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT373930B (en) | 1975-10-29 | 1984-03-12 | Basf Ag | DYE PREPARATIONS FOR DYEING AND PRINTING CELLULOSE AND CELLULOSE-CONTAINING TEXTILE MATERIAL |
| DE2832020C2 (en) * | 1978-07-21 | 1982-12-23 | Basf Ag, 6700 Ludwigshafen | Disazo dyes with pyridine coupling components, their preparation and use |
| DE3021294A1 (en) * | 1980-06-06 | 1981-12-24 | Basf Ag, 6700 Ludwigshafen | METHOD FOR COLORING COATING MASKS, ORGANIC SOLVENTS AND MINERAL OIL PRODUCTS, AND NEW DYES |
| EP0433693B1 (en) * | 1989-11-22 | 1994-02-02 | Hoechst Mitsubishi Kasei Co., Ltd. | Water-insoluble monoazo dyes and mixture thereof |
| JP3234004B2 (en) * | 1991-12-13 | 2001-12-04 | ダイスタージャパン株式会社 | Disperse dye mixture |
| DE19706245A1 (en) * | 1997-02-18 | 1998-08-20 | Basf Ag | Trifluoromethyl substituted azo dyes |
-
1972
- 1972-03-10 DE DE19722211663 patent/DE2211663C3/en not_active Expired
-
1973
- 1973-03-07 IN IN502/CAL/73A patent/IN139039B/en unknown
- 1973-03-09 BE BE128597A patent/BE796542A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE796542A (en) | 1973-09-10 |
| DE2211663A1 (en) | 1973-09-20 |
| DE2211663C3 (en) | 1975-01-16 |
| IN139039B (en) | 1976-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete disclaimer |