DE2251702A1 - DISPERSION DYES OF THE 2,6 DIAMINOPYRIDINE SERIES - Google Patents
DISPERSION DYES OF THE 2,6 DIAMINOPYRIDINE SERIESInfo
- Publication number
- DE2251702A1 DE2251702A1 DE19722251702 DE2251702A DE2251702A1 DE 2251702 A1 DE2251702 A1 DE 2251702A1 DE 19722251702 DE19722251702 DE 19722251702 DE 2251702 A DE2251702 A DE 2251702A DE 2251702 A1 DE2251702 A1 DE 2251702A1
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- red
- yellow
- orange
- amino
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/78—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/78—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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- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
- C09B29/0022—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings from diazotized aminoanthracene
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0092—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
-
- 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
- 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
-
- 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
- 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
Description
Badische Anilin- & Soda-Fabrik AG « -> r? α η η η Badische Anilin- & Soda-Fabrik AG «-> r? α η η η
lib \ /\Jllib \ / \ Jl
Unser Zeichen: Ö.Z. 29 472 Bg/Wn 6700 Ludwigshafen, 19.10.1972 Our reference: Ö.Z. 29 472 Bg / Wn 6700 Ludwigshafen, October 19, 1972
Dispersionsfarbstoffe der 2,6-Diamiraopyridinreihe Die Erfindung betrifft Farbstoffe der Formel I Disperse dyes of the 2,6-diamiraopyridine series The invention relates to dyes of the formula I
RZ
D-N=N-^i- NH-YRZ
DN = N- ^ i-NH-Y
NH-X 'NH-X '
in derin the
D den Rest einer Diazokomponente,D the remainder of a diazo component,
R Wasserstoff, gegebenenfalls substituiertes Alkyl mit 2 bisR is hydrogen, optionally substituted alkyl with 2 to
7 C-Atomen oder Phenyl,
X und Y Wasserstoff oder einen gegebenenfalls substituierten7 carbon atoms or phenyl,
X and Y are hydrogen or an optionally substituted one
Alkyl-, Cycloalkyl-, Aralkyl- oder Phenylrest und Z Wasserstoff, Carbamoyl oder Cyan bedeuten«Alkyl, cycloalkyl, aralkyl or phenyl radical and Z denotes hydrogen, carbamoyl or cyano «
Die Reste D leiten sich z.B. von Aminen der Benzol-, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe ab.The radicals D derive e.g. from amines of the benzene, benzothiazole, Benzisothiazole, thiazole, thiadiazole, thiophene, Azobenzene or anthraquinone series.
610/72 -2-610/72 -2-
409818/1004 BAD original409818/1004 BAD original
- 2 - O.Z. 2'J Λγ?- 2 - OZ 2'J Λγ?
Als Substituenten für die Reste D der Diazokomponente]! sind beispielsweise zu nennen:As substituents for the radicals D of the diazo component]! are to name for example:
In der Benzolreihe: Chlor, Brom, Nitro, Cyan, Trtfluormethyl, Methylsulfonyl, Äthylsulfonyl, Phenylsulfonyl, Carbomethoxy, Carbobutoxy, Carbo-'S-methoxyäthoxy, Carbo-ii-hydroxyMthoxy, gegebenenfalls N-mono- oder N-disubstituiertes. Carbon- oder Sulfonamid, Methyl, Äthyl, Methoxy und Äthoxy.In the benzene series: chlorine, bromine, nitro, cyano, trtfluoromethyl, Methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbomethoxy, Carbobutoxy, Carbo-'S-methoxyethoxy, Carbo-ii-hydroxyMthoxy, optionally N-mono- or N-disubstituted. Carbon or Sulfonamide, methyl, ethyl, methoxy and ethoxy.
N-Substltuenten der Carbon- oder Sulfonamide sind dabei z.B. Methyl, Äthyl, Propyl, Butyl, 3-Hydroxyäthyl, /--Hydroxypropyl, 3-Methoxyäthyl, /--Methoxy propyl oder f-"4thoxypropyl sowie das Pyrrolidid, Piperidid oder Morpholid.N-substituents of the carbon or sulfonamides are e.g. Methyl, ethyl, propyl, butyl, 3-hydroxyethyl, / - hydroxypropyl, 3-methoxyethyl, / - methoxy propyl or f- "4thoxypropyl as well as the pyrrolidide, piperidide or morpholide.
In der Azobenzolreihe: Chlor, Brom, Nitro, Cyan, Methyl, Hydroxy, ftthy1, Methoxy oder Äthoxy. In der heterocyclischen Reihe: Chlor, Brom, Nitro, Cyan, Methyl, Äthyl, Phenyl, Methoxy, 'Ithoxy, Methylmercapto, 3-Carbomethoxyäthylmercapto, ß-Carboäthoxyäthylmercapto, Carbomethoxy, Carböäthoxy, Acetyl, Methylsulfonyl oder Äthyisulfonyl.In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, Hydroxy, ftthy1, methoxy or ethoxy. In the heterocyclic Series: chlorine, bromine, nitro, cyano, methyl, ethyl, phenyl, methoxy, 'itoxy, methylmercapto, 3-carbomethoxyethylmercapto, ß-Carboäthoxyäthylmercapto, Carbomethoxy, Carböäthoxy, Acetyl, methylsulfonyl or ethyl sulfonyl.
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-Brorn-4-nitroanilin, , 2-Cyan-4-nitroanilin, 2-Methylsulfonyl-4-nitroanilin» 2-Methyl-4-nitroanilin, 2-Methoxy-4-nitroanilin,The radical D is derived in detail, for example, from the following amines: aniline, o-, m- or p-toluidine, o-, m- or. ■ .. ■ . <■■■ p-nitroaniline, o-, m- or p-cyananiline, 2,4-dicyananiline, ■■ 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 »2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline,
-5-409818/1004 BAD ORIGINAL-5-409818 / 1004 BAD ORIGINAL
' - 3 - O.'Δ. ?-9 '- 3 - O. ' Δ. ? -9
4-Chlor-2-nitroanilin, 4-Methyl-2-nitroanilin, 4-Kethoxy-2-nitroanilin, i-Amino^-trifluormethyl-^-chlorbenzol, 2-Chlor-5-3.minobenzortitril, 2-Amino-5-chlorbenzonitril, 1 -Amino-2-nitrobenzol-4-Gulfonsäure-n-butylamid oder -ß-methoxyäthylamid, 2,4-Dinitronnilin, 2,4-Dinitro-6-chloranilin, 2,4-Dinitro-6-l}ronianilin, ?,4-I>Initro-6-cyananilin, 1-Amino-2,4-dinitrobenzol-6-methylsulfon, 2,6-Dichlor-4-nitroanilin, 2,6-Dibroin-4-ni"troaiiilin, 2-Chlor-6-brom-4-nItroanilin, 2,6-Dicyan-4-nitroanilin, 2-Cyan-4-nitro-6-chloraniliri, 2-Cyan-4-nitr.o-6-bromanilint 1 -AminoT3enzol-4-methylsulfon, i-Amlno^jö-dibrom'-benzol^-niethylSuifon, 1-Amiao-2,6-dichlorbenzol-4-methylsulfon, 1-Amino-2,4-dinitrobenzol-6-earbonsäure-methylester oder -ß-methoxyäthylester, 3,5-Mchloranthranilsäure-propylester, 3,5-Dibrom-anthranilsäure-ß-methoxyäthylester, M-Acetyl-p-phenylendiamin» 4--&™in.o-acetophenon, 4- oder 2-Amino-"beHzophenon, 2- und 4-Aminodiphenylsulfon, 2-, 3- oder 4-Aminobenzoesäure-metIaylester, -äthylester, -propylester, -butylester, -isobutylestexs -ß-methoxyäthyiester, -ß-äthoxy-äthylester, -methyl-diglykolester, -äthyldiglykolester, -methyl-triglykolester, -äthyltriglykolester, -ß-hydroxyäthylester, -ß-acetoxy-äthylester, -ß-(ß'-hydroxy-äthoxy)-äthylester, -ß-hydroxy-propylester, -y-hydroxy-propylester, - (J-hydroxy-butylester, -ω-hydroxy-hexylester, 5-Nitro-amthranilsäuremethylester, -isobutylester, -methyl-diglykolestert -ß-methoxyäthylester, -ß-butoxy-äthylester-, -ß-acetoxy-äthylester,. 3- oder 4-Aminophthalsäure-, 5-Aminoisophthalsäure- oder Amino-terephthal-4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 4-kethoxy-2-nitroaniline, i-amino ^ -trifluoromethyl - ^ - chlorobenzene, 2-chloro-5-3.minobenzortitrile, 2-amino-5 -chlorbenzonitrile, 1-amino-2-nitrobenzene-4-gulfonic acid-n-butylamide or -ß-methoxyethylamide, 2,4-dinitro-niline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-l} ronianiline, ?, 4-I> initro-6-cyananiline, 1-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro-4-nitroaniline, 2,6-dibroin-4-ni "troaiiline, 2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline, 2-cyano-4-nitr.o-6-bromoaniline t 1 - AminoT3enzol-4-methylsulphone, i-Amlno ^ jö-dibromo'-benzene ^ -niethylSulfon, 1-Amiao-2,6-dichlorobenzene-4-methylsulphone, 1-amino-2,4-dinitrobenzene-6-carboxylic acid methyl ester or -ß-methoxyethyl ester, 3,5-Mchloranthranilic acid propyl ester, 3,5-Dibromanthranilic acid-ß-methoxyethyl ester, M-acetyl-p-phenylenediamine »4 - & ™ in.o-acetophenone, 4- or 2-amino - "beHzophenon, 2- and 4-aminodiphenylsulfone, 2-, 3- or 4-aminobenzoic acid metIaylester, -ät ethyl ester, propyl ester, butyl ester, isobutyl ester, -ß-methoxyethyl ester, -ß-ethoxy-ethyl ester, -methyl diglycol ester, -ethyl diglycol ester, -methyl triglycol ester, -ethyl triglycol ester, -ß-hydroxyethyl ester, -ß-acetoxy, -ß- (ß'-hydroxy-ethoxy) -ethyl ester, -ß-hydroxy-propyl ester, -y-hydroxy-propyl ester, - (J-hydroxy-butyl ester, -ω-hydroxy-hexyl ester, 5-nitro-amthranilic acid methyl ester, - isobutyl ester, methyl diglycol ester, -ß-methoxyethyl ester, -ß-butoxy-ethyl ester, -ß-acetoxy-ethyl ester. 3- or 4-aminophthalic acid, 5-aminoisophthalic acid or amino terephthalic acid
4098 18/10044098 18/1004
BAD ORIGINALBATH ORIGINAL
" 4 " O.Z. 29 472" 4 " OZ 29 472
säure-dimethylester, -diäthylester, -dipropylester, -dibutylester, 3- oder 4-Aminobenzoesäure-amid, -methylamid, -propylamid, -butylamid, -isobutylamid, -cyclohexylamid, -ß-äthyl-hexylamid, -y-methoxypropylamid, -y-äthoxy-propylamid, 2-,t 3- oder 4-AAiHO^eIiZOesäure-dimethylamid, -diäthylamid, -pyrrolidid, -morpholid, N-methyl-N-ß-hydroxy-äthylamid, 5-Amino-ieophthalsäurediamid, -bie-y-methoxy-propylamid, Aminoterephthaisäure-bis-diäthylamid, 3- oder 4-Amino-phthalsäure-imid, -fl-hydroxy-äthylamid-, y-hydroxy-propylamid, J-Amino-ö-nitro-phthalsäiire-fl-hydroxy-äthylamid, 2-, 3- oder 4-Aminobenzosulfonsäure-dimethylainid, -diäthylamid, -pyrrolididt -morpholid, Methylsulfonsäure-21-, -3'- oder 4'-amino-phenyleBter, Äthylsulfonsäure-2'-, -3'- oder -4t-amino-phenylestert Butyleulfonsäure-2'-, -31- oder -4'-aminophenylester, Benzolsulfonsäure-2'-, -31- oder 4'-aminophenylester, 2-Amino-anthrachinon, i-Amino-4-chlor-anthrachinon, 3- oder 4-Aminodiphenylenoxid, 2-Amino-1)enζ-thiazol, 2-Amino-6-car'bonsäure-methylester-'benzthiazolf 2-Amino-6-methyl-sulfonyl-benzthiazol, 2-Amino-6-cyanbenzthiazol, 2-Amino-6-nitro-benzthiazol, 5*6- oder ö^-Dichlor^-amino-benzthiazol, 4-Amino-5-brom-7-nitro-1,2-benzisothiazol, 3-Amino-5-nitxo-2t1-benzisothiazol, 3-^^0-5^1^0-7-13*0111-2,1 -benzisothiazol, 2-Aminothiazol, 2-Amino-5-nitrothiazol, 2-Amino-4-Illβthyl-thiazol-5-oarbonsäure-äthylester, 2-Amino-4-methyl-5-aoetyl-thiazolf 2-Aaino-3-cyan-4-methyl-thiophen-5-carbonsäureester, 2-Phenyl-5-amino-1»3,4-thiadiazol, 3-Methylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carbomethoxy-äthylmercapto-5-amino-1,2f4-thiadiazol·acid dimethyl ester, diethyl ester, dipropyl ester, dibutyl ester, 3- or 4-aminobenzoic acid amide, -methylamide, -propylamide, -butylamide, -isobutylamide, -cyclohexylamide, -ß-ethyl-hexylamide, -y-methoxypropylamide, - y-ethoxy-propylamide, 2-, t 3- or 4-AAiHO ^ eIiZOesäure-dimethylamide, -diethylamide, -pyrrolidid, -morpholide, N-methyl-N-ß-hydroxy-ethylamide, 5-amino-ieophthalic acid diamide, -bie -y-methoxy-propylamide, aminoterephthalic acid bis-diethylamide, 3- or 4-amino-phthalic acid-imide, -fl-hydroxy-ethylamide-, y-hydroxy-propylamide, J-amino-ö-nitro-phthalic acid-fl- hydroxyethylamide, 2-, 3- or 4-aminobenzenesulphonic acid dimethylainide, diethylamide, pyrrolidide morpholide, methylsulphonic acid 2 1 -, -3'- or 4'-aminophenyl ester, ethylsulphonic acid 2'-, -3 '- or -4 t -amino-phenyl ester t butyl sulfonic acid 2'-, -3 1 - or -4'-aminophenyl ester, benzenesulfonic acid 2'-, -3 1 - or 4'-aminophenyl ester, 2-amino-anthraquinone, i-Amino-4-chloro-anthraquinone, 3- or 4-aminodiphenylene oxide, 2-amino-1) enζ-thiazole , 2-Amino-6-carboxylic acid methyl ester-'benzthiazole f 2-Amino-6-methyl-sulfonyl-benzthiazole, 2-Amino-6-cyanobenzthiazole, 2-Amino-6-nitro-benzothiazole, 5 * 6- or ö ^ -Dichlor ^ -amino-benzothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 3-amino-5-nitxo-2 t 1-benzisothiazole, 3 - ^^ 0-5 ^ 1 ^ 0-7-13 * 0111-2,1 -benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-Illβthyl-thiazole-5-carboxylic acid ethyl ester, 2-amino-4 -methyl-5-aoetyl-thiazole f 2-aaino-3-cyano-4-methyl-thiophene-5-carboxylic acid ester, 2-phenyl-5-amino-1 »3,4-thiadiazole, 3-methylmercapto-5-amino -1,2,4-thiadiazole, 3-ß-carbomethoxy-ethylmercapto-5-amino-1,2 f 4-thiadiazole
409818/1004409818/1004
- 5 - O.Z. 22 472- 5 - O.Z. 22 472
Geeignete Diazokomponente!! der Aminoazobenzölreihe sind beispielsweise: 4-Aminoazob'enzol, 2 · , J-Mmethyl^-'-aminoazobenzol, 3'*2-Dimethyl-4-aminoazobenzol, 2,5-Dimethyl-4-äminoäzobenzol, 2-Methyl-5-methoxy-4-aminoazobenzol, 2-Methyl-4'*S-ä-imethoxy^-aminoäzö-"benzol, 4l-Chlo£~2-methyl-5-methoxy-4-"aminoazobenzol, 4!-Mtro-2-methyl-5-3nethoxy-4-aminoazobenzol, 4f-Chlor^-methyl^-aminoazobenzol, 2, 5^Diniethoxy-4-a2iiiioazobenzol, 4' -Chlor-2,5-cLimethoxy-4-aminoazobenzol, 4' -Mtro-2,5-dimethoxy-4-aminoazobenzol, 4' -Chlor- l, 5-dimethyl-4-aminoazobenzol, 4' -Methoxy-2,5-dimethyl*-4-aiainoazobenzol, 4*-Mtro-4-'aminoazobenzol, 3»5-Dibrom-4-aminoazobenzol, 2,3'-Dichlor-4-aminoazobenzol, 3-Methoxy-4-aπlinoazobenzol, 4'-Hydroxy-2'-methyl-4-aminoazöbenzol* Suitable diazo component !! the Aminoazobenzölreihe are for example: 4- Am i noa zob'enzol, 2 X, J-Mmethyl -'- ^ aminoazobenzene, 3 '* 2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-äminoäzobenzol, 2-methyl -5-methoxy-4-aminoazobenzene, 2-methyl-4 '* S-ä-imethoxy ^ -aminoäzö- "benzene, 4 l -Chl o £ ~ 2-methyl-5-methoxy-4-" aminoazobenzene, 4 ! -Mtro-2-methyl-5-3nethoxy-4-aminoazobenzene, 4-chloro ^ -methyl ^ f -aminoazobenzol, 2, 5 ^ Diniethoxy-4-a2iiiioazobenzol, 4 '-chloro-2,5-cLimethoxy-4-aminoazobenzene , 4 '-Mtro-2,5-dimethoxy-4-aminoazobenzene, 4' -chloro- l, 5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dimethyl * -4-aiainoazobenzene, 4 * - Mtro-4-'aminoazobenzene , 3 »5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene, 3-methoxy-4-aπlinoazobenzene, 4'-hydroxy-2'-methyl-4-aminoazoebenzene *
Die Reste X und Y, die gleich oder verschieden sein können, sind neben Wasserstoff beispielsweise Alkyl- mit 1 bis 8 C-Atomen, gegebenenfalls durch Hydroxy- Alkoxy mit 1 bis 8 C-Atomen, Phenoxy, Phenoxyäthoxy oder Benzyloxy substituiertes Alkyl, Cyclohexyl, Benzyl, Phenyläthyl, Phenylhydroxyäthyl, Phenylpropyl, Phenylbutyl, gegebenenfalls durch Chlor, Methyl, Methoxy oder A'thöxy substituiertes Phenyl, Polyalkoxyalkyl, HydroxypoIyalkoxyalkyl, Alkanoyloxyalkyl oder Alkoxycarbonylalkyl.The radicals X and Y, which can be the same or different, are in addition to hydrogen, for example, alkyl with 1 to 8 carbon atoms, optionally by hydroxyalkoxy with 1 to 8 carbon atoms, phenoxy, Phenoxyethoxy or benzyloxy substituted alkyl, cyclohexyl, Benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl, phenylbutyl, phenyl, polyalkoxyalkyl, hydroxypolyalkoxyalkyl, optionally substituted by chlorine, methyl, methoxy or ethoxy, Alkanoyloxyalkyl or alkoxycarbonylalkyl.
- 6 - - O.Z.- 6 - - O.Z.
Einzelne Reste X und Y sind beispielsweise: Die Alkylreste Methyl, üthyl, Propyl, Butyl, die Hydroxyalkylreste ß-Hydroxyäthyl oder -propyl, γ-Bydroxypropyl, w-Hydroxyhexyl sowie die leste 4er Formeln Individual radicals X and Y are for example: The alkyl radicals methyl, üthyl, propyl, butyl, the hydroxyalkyl radicals ß-hydroxyethyl or -propyl, γ-hydroxypropyl, w-hydroxyhexyl and the last four formulas
-GH2-CII2-O-CH2-CH2-OH, -(CH2J5-O-(CH2J4-OH1 -GH 2 -CII 2 -O-CH 2 -CH 2 -OH, - (CH 2 J 5 -O- (CH 2 J 4 -OH 1
CH, CH,CH, CH,
1 5 t 51 5 t 5
-CH-(CH0 J1-C-OH. -CH0-CH-C^H.., -CH-CH0-CH 1 2 3 1 t Z 1 0 0 2 -CH- (CH 0 J 1 -C-OH. -CH 0 -CH-C ^ H .., -CH-CH 0 -CH 1 2 3 1 t Z 1 0 0 2
CH, CH, OHCH, CH, OH
-CH2-CK-O-C6H5, -CH2-CH-C6H5, -(CH2J3-O-(CH2J2-O-C6H5, CH3 CH5 -CH 2 -CK-OC 6 H 5 , -CH 2 -CH-C 6 H 5 , - (CH 2 J 3 -O- (CH 2 J 2 -OC 6 H 5 , CH 3 CH 5
-(CH2J5-O-CH2-C6H5, -C6H5, -CH2-CH2-O-CH5, -CH2-CH2- -(CH2J5-O-(CH2J2-O-CH5, -(CH2J5-O-(CH2J2-O-(CH2J2-O-CH3, -(CH2J5-O-CH(CH5J2 und die Acyloxyalkylreste der Formeln- (CH 2 J 5 -O-CH 2 -C 6 H 5 , -C 6 H 5 , -CH 2 -CH 2 -O-CH 5 , -CH 2 -CH 2 - - (CH 2 J 5 -O - (CH 2 J 2 -O-CH 5 , - (CH 2 J 5 -O- (CH 2 J 2 -O- (CH 2 J 2 -O-CH 3 , - (CH 2 J 5 -O-CH (CH 5 J 2 and the acyloxyalkyl radicals of the formulas
-CH2-CH2-O-ACyI, -(CH2J5-O-ACyI, -CH2-CH-O-ACyI,-CH 2 -CH 2 -O-ACyI, - (CH 2 J 5 -O-ACyI, -CH 2 -CH-O-ACyI,
CH5 CH 5
-(CH2J6-O-ACyI, -(CH2J2-O-(CH2J2-O-ACyI,- (CH 2 J 6 -O-ACyI, - (CH 2 J 2 -O- (CH 2 J 2 -O-ACyI,
-CH0-CH-C^H,., wobei Acyl beispielsweise -COH, -COCH, od·» ^ ι ο 5 J.-CH 0 -CH-C ^ H,., Where acyl is for example -COH, -COCH, od · »^ ι ο 5 J.
O-Acyl -COCH9-O-C6H- sein kann. Acylreste sind ferner COOB und CONHB, wobei B Alkyl oder Aryl ist.O-acyl -COCH 9 -OC 6 H- can be. Acyl radicals are also COOB and CONHB, where B is alkyl or aryl.
Zur Herstellung der Farbstoffe der Formel I kann stan ein· Diazoverbindung von Aminen der Formel II A diazo compound of amines of the formula II can be used to prepare the dyes of the formula I
D-HH2 II,D-HH 2 II,
- T -· 409818/1004 - T - 409818/1004
- 7 - O.Z. 29 472- 7 - O.Z. 29 472
mit Kupplungskomponenten der Formel IIIwith coupling components of the formula III
jfVz injfV z in
XHN / NHY
•ansetzen, wobei D, R,X,Yund Z die angegebene Bedeutung haben.XHN / NHY
• begin, where D, R, X, Y and Z have the meaning given.
Die Biazotierung der Amine erfolgt wie üblich. Die Kupplung wird ebenfalls wie üblich in wäßrigem Medium, gegebenenfalls' unter Zusatz von Lösungsmitteln, bei schwach bis stark saurer Reaktion durchgeführt.The amines are biazotized as usual. 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 Formel III ist imThe preparation of the coupling components of the formula III is in
Prinzip in dem Patent · · (Patentanmeldung P 20 62 717.2)Principle in the patent (patent application P 20 62 717.2)
beschrieben, die Angaben dort gelten hier sinngemäß.The information there applies accordingly here.
Enthalten die erfindungsgemäßen Farbstoffe der Formel I eine Estergruppe in dem Rest X oder Y, so kann die Herstellung der Verbindungen der Formel I im Prinzip nach dem angegebenen Verfahren erfolgen, wenn die entsprechende Estergruppe schon in der Kupplungskomponente 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-, Di- oder Trichlorbenzol,If the dyes of the formula I according to the invention contain an ester group in the radical X or Y, the compounds can be prepared of the formula I can in principle be carried out by the process indicated if the corresponding ester group is already in the coupling component is included. In some cases, however, it is also useful to add the acid residue (acyl) to the finished dye Introduce Formula I. The free acids, their anhydrides, chlorides or esters are suitable for this purpose, in which case it is expedient to use inert diluents or solvents such as mono-, di- or trichlorobenzene,
409818/100 4409818/100 4
- 8 - ο.Ζ. 29- 8 - ο.Ζ. 29
Tetrahydrofuran, Dioxan, Dimethylformamid, Nitrobenzbl, N-Methylpyrrolidon oder Pyridin zugesetzt werden.Tetrahydrofuran, dioxane, dimethylformamide, nitrobenzbl, 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. NatriumcarbonatIn the esterification with free acids, it can be advantageous to use inorganic or organic catalysts, e.g. B. HCl gas or p-Toluenesulfonic acid, add and remove the resulting water to allow the reaction mixture to escape by evaporation. If acid anhydrides or chlorides are used for esterification, so The acids in question can also be used as solvents in special cases. So can the reaction with acetic anhydride perform in glacial acetic acid. When using acid chlorides as esterifying agents, it is advantageous to add to the reaction mixture to add acid-binding agents, e.g. B. sodium carbonate
Acylierungsmittel und oder -acetat, Magnesiumoxid oder Pyridin. Als Veresterungsmittel / seien im einzelnen beispielsweise genannt: Ameisensäure, Essigsäure, Chloressigsäure, sowie die Ester, Anhydride oder ChlorideAcylating agent and 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
dieser Säuren, weiterhin Chlorameisensäureäthylester oder Diketen-sowie Isocyanate.of these acids, also ethyl chloroformate or diketene as well Isocyanates.
Einzelheiten der Umsetzungen sind den Beispielen zu entnehmen.Details of the conversions can be found in the examples.
Technisch besonders wertvoll sind Farbstoffe und Farbstoffgemische der Formel I aDyes and dye mixtures are particularly valuable from a technical point of view of formula I a
A R CN A R CN
A1 A 1
N=N Z=V. NH-Y1 I aN = NZ = V. NH-Y 1 I a
NH-XNH-X
409818/1004409818/1004
- 9 - ο,ζ. 29 kfe - 9 - ο, ζ. 29 kfe
in derin the
A ITitro» Cyan, Chlor, Brom, Carbomethoxy, Carboäthoxy, ß-Methoxycarbäthoxy, Methylsulfonyl, Äthylsulfonyl, Methyl, Methoxy, Phenylsulfonyl, Phenylazo,A ITitro »cyano, chlorine, bromine, carbomethoxy, carboethoxy, ß-methoxycarbethoxy, Methylsulfonyl, ethylsulfonyl, methyl, methoxy, Phenylsulfonyl, phenylazo,
A Wasserstoff, Hit ro, Chlor, Brom» Cyan, Methyl, Methoxy., Carbomethöxy, Carboäthoxy, Methylsulfonyl,A hydrogen, hit ro, chlorine, bromine »cyano, methyl, methoxy., Carbomethoxy, Carboethoxy, methylsulfonyl,
2
A Wasserstoff, Chlor, Brom, Cyan, Methyl, Methoxy, Hitro,2
A hydrogen, chlorine, bromine, cyano, methyl, methoxy, nitro,
11
X und Y ß-Hydroxyäthyl, γ-Hydroxypropyl oder einen Rest der Formeini X and Y ß-hydroxyethyl, γ-hydroxypropyl or a radical of the formeini
/ OTT ι C\ ι /**TX ι Λ^ΤΤ ι Λ^ΤΧ 1 f\ f f^TT ι ^^TT OTT ■ /*1TT O XT/ OTT ι C \ ι / ** TX ι Λ ^ ΤΤ ι Λ ^ ΤΧ 1 f \ f f ^ TT ι ^^ TT OTT ■ / * 1TT O XT
OHOH
-(CHg)6-OH, -CH2-CH2-C6H5, -CH2-CH-C6H5, -(CH2J3-O-(CH2J2-O-CgH5,- (CHg) 6 -OH, -CH 2 -CH 2 -C 6 H 5 , -CH 2 -CH-C 6 H 5 , - (CH 2 J 3 -O- (CH 2 J 2 -O-CgH 5 ,
CH3 CH 3
— ( CH-).,—0—CHO—CjfH_, "C^En* -CnH4-O-CH^, — C^H^·—OCH7, -CH2-CH2-OCHO, -CH2-CH2-CH2-O-CHO, -CH2-CH2-OCOCH3,- (CH -)., - O — CH O —CjfH_, "C ^ E n * -C n H 4 -O-CH ^, - C ^ H ^ · -OCH 7 , -CH 2 -CH 2 -OCHO , -CH 2 -CH 2 -CH 2 -O-CHO, -CH 2 -CH 2 -OCOCH 3 ,
-CH2-CH2-O-Ch2-CH2-OCHO, -CH2-CH2-OCQCH2-O-C6H5 und Wasserstoff, und-CH 2 -CH 2 -O-Ch 2 -CH 2 -OCHO, -CH 2 -CH 2 -OCQCH 2 -OC 6 H 5 and hydrogen, and
R einen Alkylrest mit 2 bis 7 Kohlenstoffatomen oder Wasserstoff bedeuten.R is an alkyl radical having 2 to 7 carbon atoms or hydrogen.
Besonders bevorzugt sind weiterhin Farbstoffe mit mindestens einem hydroxylgruppenhaltigen Alkyl- oder Aralkyliest.Furthermore, dyes with at least one are particularly preferred hydroxyl-containing alkyl or aralkyl esters.
- 10 -- 10 -
4Ö9818/100Ä4Ö9818 / 100Ä
- 10 - Q.Z. 29- 10 - Q.Z. 29
' uch
Besonders wertvoll sind'die entsprechenden Farbstoffe, die als
Diazokomponenten gegebenenfalls durch Hitro, Chlor, Brom, Cyan,
Hethylt Ilethylmercapto, ß-Carbomethoxy-äthylmercapto, Ö-Carbonethoxyäthoxy-äthylmercapto,
Carbomethoxy oder Acetyl substituiertes
Benzthiazol, Benzisothiazol, Thiazol, Thiadiazol oder Thiophen
enthalten.'uch
Especially valuable sind'die corresponding dyes as diazo components optionally HITRO, chlorine, bromine, cyano, Hethyl t Ilethylmercapto, ß-carbomethoxy-äthylmercapto, east-Carbonethoxyäthoxy-äthylmercapto, carbomethoxy or acetyl substituted benzothiazole, benzisothiazole, thiazole, thiadiazole or thiophene contain.
Von den besonders wertvollen Diazokomponenten seien im einzelnen genannt: 4-Nitro-anilin, 2-Chlor-4-nitro-anilin, 2-Broia-4-nitrO"· anilin, 2-Cyan-4-nitro-anilin, 2-Methoxy-4-nitro-anilint 2-Amino-5-nitro-phenyl8Ulfonsäuredimethylamidt 2-Amino-5-nitro-pli*nylsulfonsäure-butylamid, Z-Amino-S-nitro-phenylsulfoneäure-ß-methoxy-äthylamid, 2-Amino-benzonitril, 3-Chlor-4-aaiino-benzonit:cilt 2-Chlor-5-amino-benzonitrilt 2-Amino-5-chlor-benzonitrilt 3t 5-Dichlor-2-amino-benzonitril, 1-Amino-2,4-dicyanbenzolt 1-A«iiio-2t4-dicyan-6-chlor-benzol, 2-Chlor-4-amino-5-nitro-benzonitΓilϊ 2-Amino-3-chlor-5-nitro-benzonitril, 2-Amino-3-brom*5-"Hitro-benzonitril, 2t6-Dicyan-4-nitro-anilin, 2l5-Dichlor-4-aitroanilinl 2t6-Dichlor-4-nitro-anilin, 2, ö-DibroB^-nitro-anilin, 2-Chlor-6-brom-4-nitro-anilin, 2,4-Dinitro-anilin, 2,4-MnItTO-O-ChIOranilin, 2t4-Dinitro-6-brom-anilin, 2-lmino-3,5-dinitro-beiizonitrili 1 -Amino-4-nitrobenzol-2-Biethylsulfon, i-Amino^-nitrobeaiol^- äthylsulfon, 4-ilethylsulfonyl-anilin, 1 -Amilιo-2-ehlorbβnβol-4-ll»βthyleulfon, i-Amino-2t6-dibroniben2ol-4^»tthylsttlfon, 1-Aaiao-2t6*&iohlor- Particularly valuable diazo components are: 4-nitro-aniline, 2-chloro-4-nitro-aniline, 2-broia-4-nitrO "· aniline, 2-cyano-4-nitro-aniline, 2-methoxy -4-nitro-aniline t 2-amino-5-nitro-phenyl8Ulfonsäuredimethylamid t 2-amino-5-nitro-pli * nylsulfonsäure-butylamid, Z-amino-S-nitro-phenylsulfonäure-ß-methoxy-ethyl-amide, 2-amino -benzonitrile, 3-chloro-4-aaiino-benzonite: cil t 2-chloro-5-aminobenzonitrile t 2-amino-5-chlorobenzonitrile t 3t 5- dichloro-2-aminobenzonitrile, 1-amino -2,4-dicyanobenzene t 1-A «iiio-2 t 4-dicyano-6-chlorobenzene, 2-chloro-4-amino-5-nitro-benzonitol ϊ 2-amino-3-chloro-5-nitro -benzonitrile, 2-amino-3-bromo * 5- "Hitro-benzonitrile, 2 t 6-dicyano-4-nitro-aniline, 2 l 5-dichloro-4-aitroaniline l 2 t 6-dichloro-4-nitro- aniline, 2, δ-dibroB ^ -nitro-aniline, 2-chloro-6-bromo-4-nitro-aniline, 2,4-dinitro-aniline, 2,4-MnItTO-O-ChIOraniline, 2 t 4-dinitro -6-bromo-aniline, 2-lmino-3,5-dinitro-beiizonitrile i 1 -amino-4-nitrobenzene-2-diethylsulfone, i-amino ^ -nitrobeaiol ^ - ethylsulfone, 4-i ethylsulfonyl-aniline, 1-amilio-2-ehlorbβnβol-4-ll »βthyleulfon, i-amino-2 t 6-dibroniben2ol-4 ^» tthylsttlfon, 1-Aaiao-2 t 6 * & iohlor-
409818/1004409818/1004
O.Z. 29 472O.Z. 29 472
benzol-4-methylsulfon, 2- und 4-Ainino-benzoesäxireester, 2-Amino-5-nitro-benzoesäureester, 2-AiIiIiIO-J-ChIOr-5-nitro-"benzoesäureester, 2-Amino-3» 5-dichlor-benzoesäureester, 2-Amino-3» 5-dibrom-benzoesäureester, 2-Amino-3»5-dinitro-benzoesäure-methylester oder -ß-methoxy-äthylester, 2-Amino-terephthalsäure-diäthylester, 4-Amino-azobenzol, 2,3 ·-Dimethyl-4-amino-azobenzol, 21,3-Mmethyl-4-amino-azobenzol, 2,5-Diπlethyl-4-amino-azobenzol, 3»5-I>ibrom-4-amino-azobenzol. benzene-4-methylsulfone, 2- and 4-amino-benzoic acid esters, 2-amino-5-nitro-benzoic acid esters, 2-AiIiIiIO-J-ChIor-5-nitro- "benzoic acid esters, 2-amino-3» 5-dichloro- benzoic acid ester, 2-amino-3 »5-dibromo-benzoic acid ester, 2-amino-3» 5-dinitro-benzoic acid methyl ester or -β-methoxy-ethyl ester, 2-amino-terephthalic acid-diethyl ester, 4-amino-azobenzene, 2 , 3 · -Dimethyl-4-amino-azobenzene, 2 1 , 3-Mmethyl-4-amino-azobenzene, 2,5-dimethyl-4-amino-azobenzene, 3 »5-I-bromo-4-amino-azobenzene .
Von den besonders wertvollen heterocyclischen Biazokomponenten seien erwähnt: 2-Amino-5-nitro-thiazol, 2-Amino-4-Eiethyl-5-n-itro·» thiazol, 2-Amino-4-πιethyl-thiazol-5-carbonsäureäthylester, 2-Amino-5-phenyl-1,3»4-thiadiazol, 3-Phenyl-5-amino-1,2,4-thiadiazol, 3-Methyl-mercapto-5-amino=1 92,4-thiadiazol9 3-ß-Carbomethoxy-äthylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carboäthoxy-äthylmercapto-5-amino-1,2,4-thiadiazol, 2-Amino-6~cyan™benzthiazol, 2-Amino-6-carbonsäuremethylester-benzthiazol, 2-Amino-6«'nitxo-benzthiazol, 2-AHlino-3-cyan-4-Jnethyl-thiophen-5-carbonester, 3-Amino-5-nitro-2,1-benzisothiazol, 3-Amino-5-nitro~7-chlor-2,1-benzisothiazol, 3-Ämino-5-nitro-7-brom-2,1-benzisothiazol, ^-Amino-l-nitxo^,2-benzisothiazol, 4-Amino-5-brom-1,2-benzisothiazol, 4--AmIIiO-7-nitro-1,2-benzisothiazol, 4-Amino-5-cyan-7-nitro-1,2-benzisothiazol, 4-Amino-5-chlor-7-nitro-1,2-benzisothiazol.Of the particularly valuable heterocyclic biazo components are mentioned: 2-amino-5-nitro-thiazole, 2-amino-4-ethyl-5-n-itro · »thiazole, 2-amino-4-πιethyl-thiazole-5-carboxylic acid ethyl ester, 2-Amino-5-phenyl-1,3 »4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-methyl-mercapto-5-amino = 1 9 2 , 4-thiadiazole 9 3-ß-Carbomethoxy-ethylmercapto-5-amino-1,2,4-thiadiazole, 3-ß-Carboethoxy-ethylmercapto-5-amino-1,2,4-thiadiazole, 2-Amino-6 ~ cyan ™ benzthiazole, 2-Amino-6-carboxylic acid methyl ester-benzothiazole, 2-Amino-6 "'nitxo-benzothiazole, 2-AHlino-3-cyano-4-methyl-thiophene-5-carboxylate, 3-amino-5-nitro-2,1 -benzisothiazole, 3-amino-5-nitro ~ 7-chloro-2,1-benzisothiazole, 3-Ämino-5-nitro-7-bromo-2,1-benzisothiazole, ^ -amino-l-nitxo ^ , 2- benzisothiazole, 4-amino-5-bromo-1,2-benzisothiazole, 4 - AmIIiO-7-nitro-1,2-benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzisothiazole, 4 -Amino-5-chloro-7-nitro-1,2-benzisothiazole.
- 12 -- 12 -
09 818/100 409 818/100 4
- 12 - O.Z. 29 472- 12 - O.Z. 29 472
Die neuen Farbstoffe sind gelb bis blau und eignen sich zum Färben von Textilmaterialien aus Acrylnitrilpolymerisaten, synthetischen Polyamiden, Celluloseestern, wie 2 1/2- oder Triacetat, und insbesondere von synthetischen linearen Polyestern, wie Polyäthylenglykolterephthalat oder chemisch analog aufgebauten Polymeren.The new dyes are yellow to blue and are suitable for dyeing of textile materials made of acrylonitrile polymers, synthetic Polyamides, cellulose esters such as 2 1/2 or triacetate, and in particular of synthetic linear polyesters such as polyethylene glycol terephthalate or polymers with a chemically analogous structure.
Die Farbstoffe können aus organischen Lösungsmitteln wie z. B. Perchloräthylen, nach dem Transfer-Verfahren und insbesondere auch aus wäßrigen Dispersionen und nach dem Thermosolverfahren appliziert werden. Man erhält farbstarke Färbungen, die sich durch hervorragende Echtheiten auszeichnen.The dyes can be prepared from organic solvents such as. B. perchlorethylene, applied by the transfer process and in particular also from aqueous dispersions and by the thermosol process will. Strong dyeings are obtained which are distinguished by excellent fastness properties.
Die Angaben über Teile und Prozente beziehen sich in den Beispielen auf das Gewicht, wenn es nicht anders vermerkt ist.The data on parts and percentages relate to the examples on weight, unless otherwise noted.
409818/1004409818/1004
ο.Ζ. 29 472ο.Ζ. 29 472
Ein Gemisch aus 187 Teilen 2,6-Dichlor-^-cyan-4-äth7/-lpyridin, 500 Teilen !-!ethanol und 135 Teilen 2-Phenylpropylamin-(i ) wird eine Stunde bei ungefähr 25 bis maximal 55 C gerührt, dann setzt man 105 Teile Triäthylamin innerhalb von 15 Minuten zu und rührt weitere 6 Stunden bei ungefähr 45 "bis 55 0C. Dann destilliert man unter vermindertem Druck bei 50 bis 55 °C etwa 250 Raumteile Methanol und überschüssiges Triäthylamin ab, läßt etwas abkühlen und gibt denA mixture of 187 parts of 2,6-dichloro - ^ - cyano-4-eth7 / -lpyridine, 500 parts of! -! Ethanol and 135 parts of 2-phenylpropylamine- (i) is stirred for one hour at about 25 to a maximum of 55 ° C, then sets to 105 parts of triethylamine within 15 minutes and stirred for a further 6 hours at about 45 "to 55 0 C. then distilled under reduced pressure at 50 to 55 ° C about 250 parts by volume of methanol and excess of triethylamine from, allowed to cool slightly and gives the
Rückstand unter Rühren in ein Gemisch aus etwa 1500 Teilen Wasser, 500.Teilen Eis und 50 Teilen konzentrierter Salzsäure. Man rührt noch 1 Stunde, saugt den ausgefallenen Niederschlag ab und trocknet. Man erhält etwa 265 Teile eines farblosen Pulvers, das bei 85 bis 90 0C schmilzt.Mix the residue with stirring in a mixture of about 1500 parts of water, 500 parts of ice and 50 parts of concentrated hydrochloric acid. The mixture is stirred for a further 1 hour, the precipitate which has separated out is filtered off with suction and dried. About 265 parts of a colorless powder which melts at 85 to 90 ° C. are obtained.
27,5 Teile dieses Pulvers werden mit etwa 60 Teilen ß-Hydroxyäthylamin 4 his 5 Stunden bei 130 "bis 155 C gerührt. Dann läßt man erkalten und versetzt das Gemisch mit^ 200 Raumteilen Eisessig und 30 Raumteilen konzentrierter Salzsäure. Man erhält eine Lösung der Kupplungskomponente der wahrscheinlichen Formel27.5 parts of this powder are mixed with about 60 parts of ß-hydroxyethylamine Stirred for 4 to 5 hours at 130 "to 155 ° C. It is then allowed to cool and the mixture is mixed with ^ 200 parts by volume of glacial acetic acid and 30 parts by volume of concentrated hydrochloric acid. A solution of the coupling component of the probable formula is obtained
CN CH,CN CH,
ι 5ι 5
ITH-CH2-CH2-OHITH-CH 2 -CH 2 -OH
- 14 -- 14 -
40-981 8/-1 0 0.440-981 8 / -1 0 0.4
0.2. 29 4f20.2. 29 4f2
die einen kleineren Anteil der Kupplungskomponente der wahrschein lichen Formelwhich has a smaller proportion of the coupling component of the probable union formula
C2H5CN C 2 H 5CN
enthält.contains.
Das Kupplungskomponentengemisch wird mit etwa 50 Teilen Eis versetzt und auf etwa 0 C abgekühlt. Dann gibt man in Anteilen gleichzeitig etwa 100 Teile Eis und eine Lösung von diazotiertem 2-Amino-5-nitrobenzonitril zu, die wie folgt hergestellt wird» 16,3 Teile 2-Amino-5-nitrobenzonitril werden unter Rühren bei 0 bis 4 C so in ein Gemisch aus 50 Teilen konzentrierter Schwefelsäure und 13 Teilen 23 ^iger liitrosylschwefelsäure gegeben» daß die Temperatur zu keiner Zeit über 4 C steigt. Man rührt 4 Stunden bei 0 bis 5 C und kuppelt dann,wie oben beschrieben. Zur raschen Beendigung der Kupplung, die bei etwa 0 0C verlaufen soll, wird der pH des Gemisches durch Zugabe von Natriumacetat auf den Wert von 1,5 bis 2,5 eingestellt. Falls das Gemisch während der Kupplung schwer rührbar wird, kann man Eiswasser zusetzen. Man rührt das Gemisch noch 1 Stunde, erhitzt dann mit Wasserdampf auf 60 bis 80 C, saugt ab, wäscht mit Wasser und trocknet. Man erhält etwa 47 Teile eines rotbraunen Pulvers der wahrscheinlichen FormelAbout 50 parts of ice are added to the coupling component mixture and the mixture is cooled to about 0.degree. About 100 parts of ice and a solution of diazotized 2-amino-5-nitrobenzonitrile, which is prepared as follows, are then added in portions at the same time: 16.3 parts of 2-amino-5-nitrobenzonitrile are so stirred at 0 to 4 ° C added to a mixture of 50 parts of concentrated sulfuric acid and 13 parts of 23% liitrosylsulphuric acid so that the temperature never rises above 4 ° C. The mixture is stirred for 4 hours at 0 to 5 ° C. and then coupled as described above. To quickly end the coupling, which should take place at about 0 ° C., the pH of the mixture is adjusted to a value of 1.5 to 2.5 by adding sodium acetate. If the mixture becomes difficult to stir during coupling, ice water can be added. The mixture is stirred for a further hour, then heated to 60 to 80 ° C. with steam, filtered off with suction, washed with water and dried. About 47 parts of a red-brown powder of the probable formula are obtained
- 15 -4098 1 8/ 1004- 15 -4098 1 8/1004
- 15 - O.ζ. 29- 15 - O.ζ. 29
CN 0^CN CH3 CN 0 ^ CN CH 3
NH-CH2-CH2-OHNH-CH 2 -CH 2 -OH
das einen kleineren Fartstoffanteil des 2,6-Alkylaminopyridin-Isomeren enthält, sich in Dimethylformamid mit roter Farbe löst und Polyäthylenterephthalat-Gewebe in kräftigen roten Tönen mit vorzüglichen Echtheiten färbt.that has a smaller proportion of the solids content of the 2,6-alkylaminopyridine isomer contains, dissolves in dimethylformamide with red color and polyethylene terephthalate fabric in strong red tones with excellent Dyes fastness properties.
16,5 Teile der Diazokomponente der Formel16.5 parts of the diazo component of the formula
COOCH2CH2OCH3 COOCH 2 CH 2 OCH 3
0„N -V Τ" NH,0 "N -V Τ" NH,
werden mit 180 Raiimteilen Eisessig5 18 Raumteilen konzentrierter
Salzsäure und 20 Raumteilen Wasser versetzt. Man kühlt auf 0 bis 5 0C ab, tropft I9 Raumteile 23 $ige Natriuranitritlösung zu und
rührt 2 bis 5 Stunden bei 0 bis 5 C. Dann verdünnt man die
DiazoniumsalzlÖsung mit etwa 800 Teilen Eiswasser, zerstört überschüssige
salpetrige Säure wie üblich und versetzt das Diazoniumsalzgemisch in Anteilen mit 19»5 Teilen einer Lösung oder Suspension
der Kupplungskomponente der Formelare treated with 180 of glacial acetic acid Raiimteilen 5 18 parts by volume of concentrated hydrochloric acid and 20 parts by volume of water. It is cooled to 0 to 5 0 C., dropwise I9 space parts 23 $ strength Natriuranitritlösung added and stirred for 2 to 5 hours at 0 to 5 C. Then the mixture is diluted
Diazonium salt solution with about 800 parts of ice water, destroys excess nitrous acid as usual and adds 19-5 parts of a solution or suspension of the coupling component of the formula to the diazonium salt mixture
- 16 -- 16 -
409818/1Q(H409818 / 1Q (H.
- 16 - O.Z. 29 472- 16 - O.Z. 29 472
C5H7 (η)
ClIC 5 H 7 (η)
ClI
in einem Gemisch aus 150 Teilen Eisessig, 20 Teilen konzentrierter Salzsäure und etwa 30 Teilen Wasser. Während der Kupplung kühlt man durch Zugabe von etwas Eis auf 0 bis 5 C und setzt verdünnte Matronlauge zu, bis der pH-Wert des Gemisches etwa 2,5 beträgt. Nach beendeter Kupplung verdünnt man das Gemisch mit etwa 1000 Teilen Wasser, saugt den ausgefallenen Farbstoff der Formelin a mixture of 150 parts of glacial acetic acid, 20 parts more concentrated Hydrochloric acid and about 30 parts of water. You cool down during the clutch by adding some ice to 0 to 5 C and continues diluted Add matron lye until the pH of the mixture is around 2.5. After the coupling has ended, the mixture is diluted with about 1000 parts Water, soaks up the precipitated dye of the formula
COOCH-CH-OCH CH (n) <L ά ? ^ 'CNCOOCH-CH-OCH CH (n) <L ά ? ^ 'CN
N = N /^N = N / ^
NH-CH2-CH2-OHNH-CH 2 -CH 2 -OH
ab, wäscht mit Wasser und trocknet.off, wash with water and dry.
Man erhält ein dunkelrotes Pulver, das sich in Dimethylformamid mit roter Farbe löst und Polyäthylenterephthalatgewebe nach Hochtemperatur-Färbeverfahren in kräftigen roten Tönen mit sehr guten Echtheiten färbt.A dark red powder is obtained, which dissolves in dimethylformamide with red color dissolves and polyethylene terephthalate fabric after high-temperature dyeing process dyes in strong red shades with very good fastness properties.
- 17 -- 17 -
409818/1004409818/1004
- 17 - O.Z. 29 4?2- 17 - O.Z. 29 4? 2
• 22517• 22517
22 Teile 2,6-Dxchlor-3-cyan-4-(n)-propjlpyridin werden mit 100 Teilen !-!ethanol gelöst, dann gibt man bei 45 bis 55 C 15 Teile des Amins der Formel HN-(GH2),-0(CHp)-OH zu, rührt 30 Minuten, versetzt mit 20 Teilen Triäthylamin und rührt weitere 5 Stunden bei 45 bis 55 G* Dann destilliert man nach Zugabe von 30 Teilen γ-Hydroxypropylamin Methanol und Triäthylamin ab und rührt den' Rückstand 4 Stunden bei 130 bis 145 C Nach dem Erkalten wird daa Reaktionsgemisch mit 60 Raumteilen Dimethylformamid versetzt und unter Rühren zu folgender Diazoniumsalzlösung gegeben: 13»8 Teile p-Nitroanilin werden mit 100 Raumteilen Wasser und 30 Raumteilen konzentrierter Salzsäure 1 Stunde gerührt, dann gibt man etwa 160 Raumteile Wasser zu, kühlt auf 0 °C ab, versetzt mit 33 Raumteilen 23 ^iger Uatriumnitritlösung, rührt 2 Stunden, filtriert und zerstört einen etwa vorhandenen Überschuß an salpetriger Säure wie üblich.22 parts of 2,6-chloro-3-cyano-4- (n) -propylpyridine are dissolved in 100 parts of! -! Ethanol, then 15 parts of the amine of the formula HN- (GH 2 ) are added at 45 to 55 C, -0 (CHp) -OH, stirred for 30 minutes, mixed with 20 parts of triethylamine and stirred for a further 5 hours at 45 to 55 G * Then, after the addition of 30 parts of γ-hydroxypropylamine, methanol and triethylamine are distilled off and the residue 4 is stirred Hours at 130 to 145 ° C. After cooling, 60 parts by volume of dimethylformamide are added to the reaction mixture and the following diazonium salt solution is added with stirring: 13 »8 parts of p-nitroaniline are stirred with 100 parts by volume of water and 30 parts by volume of concentrated hydrochloric acid for 1 hour, then added for about 160 parts by volume of water are added, the mixture is cooled to 0 ° C., 33 parts by volume of 23% sodium nitrite solution are added, the mixture is stirred for 2 hours, filtered and any excess of nitrous acid that may be present is destroyed as usual.
Das Kupplungsgemisch läßt man 1 Stunde sauer rühren, dann setzt man wäßrige natronlauge zu, bis der pH-Wert des Gemisches etwa 2 beträgt, saugt den ausgefallenen Farbstoff ab, wäscht mit Wasser und trocknet.The coupling mixture is allowed to stir acidic for 1 hour, then it is set aqueous sodium hydroxide solution until the pH of the mixture is about 2, sucks off the precipitated dye, washes with water and dries.
Man erhält etwa 50 Teile eines roten Farbstoffpulvers der FormelAbout 50 parts of a red dye powder of the formula are obtained
V/ \VN=HV / \ VN = H
- 18 - O.Z. 29 K7Z - 18 - OZ 29 K7Z
(η) CN νχ ^IiH-CH2-CH2-CH2-O-CH2-CH2-CH2-CH2-OH (η) CN νχ ^ IiH-CH 2 -CH 2 -CH 2 -O-CH 2 -CH 2 -CH 2 -CH 2 -OH
HH-CHn-CIU-CH0-OHHH-CH n -CIU-CH 0 -OH
das einen kleineren Anteil des Farbstoffes der Formelthat a smaller proportion of the dye of the formula
C5Ii7 (n) CNC 5 Ii 7 (n) CN
V-HV-H
o2nY/ \Vk-io 2 nY / \ Vk-i
enthält und Polyäthylenterephthalatgewebe in kräftigen orangefarbenen Tönen mit vorzüglichen Echtheiten nach Hochtemperatür-Färbeverfahren färbt. Farbe der Lösung in Dimethylformamid: rotstichiges orange.Contains and polyethylene terephthalate fabric in bright orange Shades with excellent fastness properties after high-temperature dyeing processes colors. Color of the solution in dimethylformamide: reddish orange.
10 Teile des Farbstoffes der Formel10 parts of the dye of the formula
C5H7 (n)
ClT
Cl ft~ C 5 H 7 (n)
ClT
Cl ft ~
Cl NH-CH2-CH2-CH2-OHCl NH-CH 2 -CH 2 -CH 2 -OH
werden mit Θ0 Raumteilen im©isensäure 10 Staaten unter. S&ckflußkühlung gerührt,· dann destilliert man etwa JO Eawrtailewith Θ0 parts of volume in © isenic acid 10 states below. Reflux cooling stirred, · then about JO Eawrtaile is distilled
säure ab» versetzt den Rückstand mit etwa. 151Q Teilen Vaseex,acid off »adds about. 15 1 Q Share Vaseex,
409818/1004409818/1004
O.Z. 29 472O.Z. 29 472
erkalten, saugt den Farbstoff der Formelcool, soaks up the dye of the formula
C5H7 (n)
CN yjS
C1-^\\_N=N "4 />- NH-CH2-CH2-CH2-OCHoC 5 H 7 (n)
CN yjS
C1 - ^ \\ _ N = N "4 /> - NH-CH 2 -CH 2 -CH 2 -OCHo
Cl NH-CH2-Ch2-CH2-OCHO ·Cl NH-CH 2 -Ch 2 -CH 2 -OCHO
ab, wäscht mit Wasser und trocknet. Man erhält ein scharlachrotes Pulver, das sich in Dimethylformamid orangefarben löst und PoIyäthylenterephthalatgewebe in orangefarbenen Tönen mit sehr guten Echtheiten färbt.off, wash with water and dry. A scarlet powder is obtained, which dissolves in orange dimethylformamide, and polyethylene terephthalate fabric dyes in orange shades with very good fastness properties.
11,8 Teile 2-Aminobenzonitril werden in 300 Raumteilen Wasser und /!'." Raumteilen konzentrierter Salzsäure gelöst. Dann gibt man 300 Teile Bis und 33 Raumteile 23 '^ige Hatriumnitritlösung hinzu, rührt das Gemisch 2 Stunden bei 0 bis 5 C- und filtriert. Ein etwa vorhandener Überschuß an salpetriger Säure wird wie üblich zerstört, dann läßt man die Diazoniumsalzlosung unter Rühren zu einer auf 5 C-abgekühlten Lösung oder Suspension von 24 Teilen der Kupplungskomponente der Formel11.8 parts of 2-aminobenzonitrile are dissolved in 300 parts by volume of water and / or parts by volume of concentrated hydrochloric acid. 300 parts of bis and 33 parts by volume of 23% sodium nitrite solution are then added and the mixture is stirred at 0 to 5 ° C. for 2 hours. Any excess nitrous acid present is destroyed as usual, then the diazonium salt solution is left with stirring to form a solution or suspension of 24 parts of the coupling component of the formula which has been cooled to 5 C
CoHc CoH c
NH-Ch0-CH0-O-CO-CH0-O-C-EL ά ά do? NH-Ch 0 -CH 0 -O-CO-CH 0 -OC-EL ά ά do?
- 20 -- 20 -
409818/1004 BAD ORIGINAL409818/1004 ORIGINAL BATHROOM
- 20 - O.Z. 29 472- 20 - O.Z. 29 472
in einem Gemisch aus etwa 5OO Teilen Wasser und 20 Teilen Salzsäure laufen. Man rührt die saure Mischung etwa I5 Minuten und gibt dann innerhalb von etwa 30 Minuten wäßrige Natronlauge zufbis der pH-Wert des Kupplungsgemisches etwa 3 ist. Nach Rühren über Nacht wird der Farbstoff der Formelrun in a mixture of about 500 parts of water and 20 parts of hydrochloric acid. The acidic mixture was stirred for about l5 minutes, and then within about 30 minutes aqueous sodium hydroxide solution to f until the pH of the coupling mixture is about 3. After stirring overnight the dye becomes of the formula
C2II5
CNC 2 II 5
CN
N
NH-CH0-CH0-O-COCH0-O-C^h,.N
NH-CH 0 -CH 0 -O-COCH 0 -OC ^ h ,.
abfiltriert, mit Wasser gewaschen und getrocknet. Man erhält ein gelbes Pulver, das sich in Dimethylformamid mit gelber Farbe löst und Polyathylenterephthalatgewebe in kräftigen gelben Tönen mit vorzüglichen Echtheiten färbt.filtered off, washed with water and dried. A yellow powder is obtained which dissolves in dimethylformamide with a yellow color and dyes polyethylene terephthalate fabric in strong yellow shades with excellent fastness properties.
Analog zu den in den Beispielen 1 bis 5 beschriebenen Arbeitsweisen werden die in den folgenden Tabellen beschriebenen Farbstoffe hergestellt.Analogous to the procedures described in Examples 1 to 5 the dyes described in the following tables are produced.
Die Farbtonangabe in den Tabellenbeispielen bezieht sich auf Färbungen auf Polyathylenterephthalatgewebe.The color shade information in the table examples relates to colorations on polyethylene terephthalate fabric.
- 21 -- 21 -
409818/1004409818/1004
-■ 21 -- ■ 21 -
OvZ. 29OvZ. 29
CU R GUCU R GU
M-YM-Y
KH-XKH-X
2 ι by
OH-CH 0 -GH-CrH 1 ,
2 ι by
OH
2 ι b 5
OH ΓίΤΤ ΓΙ TI / ™ 1 TJ
2 ι b 5
OH
^ ι ο y
' OH-CH 0 -CH-CrHr-
^ ι ο y
' OH
j -C 3 H 7 (η)
j
2 ι ο 3
OH rtTT λιTT * ^ t TT
2 ι ο 3
OH
: om ! "2" ii "" β 5
: om
2;2 -2 ; 2 -
O. Z. 29O. Z. 29
TOf bluish tint
TOf
OE-CH 2 -CH-C 6 H 5
OE
I -:■ ,. i red,
I -: ■,.
iSStii/1iSStii / 1
Ό.Ζ. 29 472Ό.Ζ. 29 472
-CHg-OH-CHg-CHg-CHg-CH 2 -CHg-
-CHg-OH
-CHg-OH-CH 2 -CH 2 -CHg-CHg-CHg-
-CHg-OH
d , 6 5
OH—CH 0 —CH-C / -Hr-
d , 6 5
OH
409818/1004409818/1004
- 24 -- 24 -
O.Z. 29 '472O.Z. 29 '472
- 25 -- 25 -
409818/1006409818/1006
-ZS-ZS
ο« ζ. 29 472ο «ζ. 29 472
CN R ClTCN R ClT
ITH-YITH-Y
Cl HÜ-XCl HÜ-X
2 ι 6 5
OH-CH 0 -CH-C ^ H 1 -
2 ι 6 5
OH
OH2) 65
OH
** \j χι« ~ u Jl *- O /· Ji p-
2 ι 6 5
OH / ™ ITT / TCT Ci XT
** \ j χι «~ u Jl * - O / · Ji p-
2 ι 6 5
OH
409818/1004409818/1004
0.2. 29 *70.2. 29 * 7
*"" I/IIa ·' V/ Ju-*■" ν/"· \j Ja.« ■■" w Jl^ *" ^ Π
^jJL fm £». f% ττ jpiTT / \ Λττ / ^ O Λ TX
* "" I / IIa · 'V / Ju- * ■ "ν /" · \ j Yes. «■■" w Jl ^ * "^ Π
^ jJL fm £ ».
rotbluish tint
Red
rotbluish tint
Red
2 , 6 5
OH-CH 0 -CH-C ^ H 1 .
2, 6 5
OH
rotbluish tint
Red
rotbluish tint
Red
2 ι 6 5
OH-CH 0 -CH-C ^ Hi-
2 ι 6 5
OH
rotbluish tint
Red
rotbluish tint
Red
ro* ,s : · «;.bluish tint
ro *, s : · «;.
rot ' ■'■ " bluish
red '■' ■ "
I I/XI« / -» ""Vl V ** "■*** J jj Va/JutI I / XI «/ -» "" Vl V ** "■ *** J yy Va / Jut
rotbluish tint
Red
rotbluish tint
Red
409818/1004409818/1004
O.ζ- 29O.- 29
CIT R CNCIT R CN
N=N-Z=X. NH-YN = N-Z = X. NH-Y
Br HN-XBr HN-X
ίΐ ι O 5-CH n -CH-Cz-H, -
ίΐ ι O 5
OHI •
OH
- 28 -- 28 -
409818/1004409818/1004
O.Z. 29O.Z. 29
rotbluish tint
Red
rotbluish tint
Red
OH-CH 2 -CH-C 6 H 5
OH
rotbluish tint
Red
rotbluish tint
Red
2 ι O 5
OH-CH_-CH-C £ H C
2 ι O 5
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
- 29 -- 29 -
409818/1004409818/1004
0,7,. 29 2^T2 0.7 ,. 29 2 ^ T2
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rH: vrH: v
NO R CNNO R CN
OJ-AO YES
2 Λζζ/ 2 Λζζ /
NH-XNH-X
0,2. 29 '!720.2. 29 '! 72
C2H5 -CH-C 4 H,
C 2 H 5
OH-CHg-CH-C 6 H 5
OH
2 I 6 5
OH-CH-CH-CH,
2 I 6 5
OH
A09818/1004A09818 / 1004
O.Z. 29 472O.Z. 29 472
rotbluish tint
Red
5 7-CE
5 7
2 1 6 D -CE 0 -CH-C ^ H, -
2 1 6 D
OE«- ι ^ j
OE
2 I 6 5-CE n -CH-C ^ H 1 .
2 I 6 5
Cl DO-CH 0 -CE-C ^ E 1 .
Cl DO
OE- I w - /
OE
- 32 -- 32 -
A09818/1004 -A09818 / 1004 -
O.Z. 29 472OZ 29 472
4_ (L L·. . -CH 9 -CH 9 -CH-OH
4_ (LL ·..
ϊ_ U -C 2 H 5
ϊ_ U
409818/TQCU409818 / TQCU
-JS --JS -
0.3. 29 V^0.3. 29 V ^
onon
Cl R CNCl R CN
N=N ~vy- 1 N = N ~ vy- 1
NH-YNH-Y
Rι
R.
Farbton 1
hue
^ I \jXX _ j __ W"~ V OXl a J j "Π^ I \ j XX _ j __ W "~ V OXl a J j" Π
^j 2 4-ι Λίτΐ jf ^ ι / ** tt ι Ott
^ j 2 4-
OH-CH 2 -CH-C 6 H 5
OH
409818/10Ö4409818 / 10Ö4
- 34 -- 34 -
O.Z. 29 472O.Z. 29 472
OHI ο '
OH
"" ι V/XX 7 -φ KJ ·™ V O£La% / λ *^ ζ' r~"" ι V / XX 7 -φ KJ · ™ VO £ La% / λ * ^ ζ 'r ~
ά 2 ? -CH 9 -CH -CH 9 -O-CH,
ά 2 ?
- 35 -- 35 -
409818/1004409818/1004
ο. ζ. 29ο. ζ. 29
rotyellowish
Red
rotyellowish
Red
2 5-CH
2 5
40981 8/ .1.0 0.440981 8 / .1.0 0.4
Br R CNBr R CN
ν 2 Ν=ν 2 Ν =
NH-YNH-Y
NH-XNH-X
O.Z. 29 472O.Z. 29 472
5 2 4- (CEL) -O- (CH) -OH
5 2 4
Cl Oj -CH - CH-C, H
Cl Oj
409818/1004409818/1004
O.Z. 29 4/2O.Z. 29 4/2
OH-CH 2 -CH-CgH 5
OH
- 58 - - 58 -
409818/1004409818/1004
0.3. 390.3. 39
rotyellowish
Red
rotyellowish
Red
409818/1004409818/1004
O. Z. 2SJ kr;2 OZ 2SJ k r ; 2
R CNR CN
O Ji -f X= O Ji -f X =
NH-YNH-Y
IiH-XIiH-X
2 ( 05
OH-CH 0 -CH-C, H 1 .
2 (05
OH
2 1 6 5
OH-CH 0 -CH-C ^ H 1 .
2 1 6 5
OH
2 2-CH -CH-OH
2 2
ges orangerotstichi
total orange
409618/1004409618/1004
- 40 -- 40 -
u.Z. £9u.z. £ 9
RR.
!
OHI.
!
OH
ges orangerotstichi
total orange
ge s orangerotstichi
ge s orange
orangereddish
orange
2 l -CH -CH-OH
2 l
ges orangerotstichi
total orange
2 2 2 2-CH -CH -0-CH -CH 0 -OH
2 2 2 2
409818/1004409818/1004
- 41 -- 41 -
mm V OXX / \j *■· ι OXX ) '. *"™ w XX mm V OXX / \ j * ■ ι OXX ) '. * "™ w XX
orange ι
orange
2 ι 6 5
OH-CH 0 -CH-C ^ H
2 ι 6 5
OH
2 t- 2 ^- - (CH) -0- (CH) 0 -OCHO
2 t- 2 ^ -
- 42 -- 42 -
409818/1004409818/1004
OnIIO n II
NaK--ν/Λ- ME-YNaK - ν / Λ- ME-Y
IiH-XIiH-X
0,7. 29 47?0.7. 29 47?
Pι
P.
ν 2 3 2'4- (CH) -0- (CE) -OH
ν 2 3 2'4
2 ι 6 5
OE-CH 0 -CH-C ^ E 1 .
2 ι 6 5
OE
OH-CH 2 -CH-C 6 H 5
OH
*"* V \/Χ1 J —τ"~ \J *"■ V, ν/Xl λ* "* V \ / Χ1 J -τ " ~ \ J * "■ V, ν / Xl λ
- 43 -- 43 -
409818/1004409818/1004
u.Z. 29 472u.z. 29 472
2 2-CH -CH -OH
2 2
2 l 6 5
CH3
--CH -CH-C H
2 l 6 5
CH 3
-
2 2-CH-CH -OH
2 2
2 I 6 5
CH3
1-CH -CH-C, E
2 I 6 5
CH 3
1
174173
174
-C3H7U)-C 2 H 5
-C 3 H 7 U)
O OO O
I II I
cm CJcm CJ
tu tudo do
CJ CJCJ CJ
IU IUIU IU
'0 ü'0 above
rubinrotRuby red
Ruby red
2 1 65
OH-CH 0 -CH-C ^ H 1 .
2 1 65
OH
d -> \
0H5-CH- (CH 0 ), -C-OH
d -> \
0H 5
- 44. -- 44. -
4098 18/10044098 18/1004
0.2. 290.2. 29
C6H5-CH-CH-O-CO-CH 2 -O-
C 6 H 5
- 45 -- 45 -
409818/100,4 ,409818 / 100.4,
O.Z. 29 472O.Z. 29 472
CU R CN NH-XCU R CN NH-X
2 ι 6 5
OH-CH 0 -CH-C ^ -H
2 ι 6 5
OH
409818/1004409818/1004
CZ. 29 472CZ. 29 472
bis orangegolden yellow
to orange
bis orangegolden yellow
to orange
c. \ OS-CH -CH-CH
c. \ OS
409818/1004409818/1004
- 47 -- 47 -
O.Z. 29 472O.Z. 29 472
CH5 -CH 2 -CH-C 6 H 5
CH 5
2 ι op
OH,-CH 0 -CH-C ^ H, -
2 ι op
OH,
2 ι 65
CH5 -CH -CH-Cx-H
2 ι 65
CH 5
2 2-CH -CH -OH
2 2
OH-CH 2 -CH-C 6 H 5
OH
40981.87 10.04.40981.87 04/10.
CN R CN /7 V^N=N-/' XV NH-YCN R CN / 7 V ^ N = N- / ' X V NH-Y
NH-XNH-X
O Z. 29 472O line 29 472
gelbgreenish
yellow
gelbgreenish
yellow
gelbgreenish
yellow
C2H5 -CH-C 4 H 9
C 2 H 5
409818/1004409818/1004
- 49 -- 49 -
O. Z. 29 47dO. Z. 29 47d
Xί
X
: -CH2-CEg-OE1
: -CH 2 -CEg-OE
OE-CEg-CE-C I
OE
OE-CE 2 -CE-CgE 5
OE
ά ι 6 ς
OE ° -CE 0 -CH-C E
ά ι 6 ς
OE °
2 ι 6 5
OE-CH 9 -CH-C ^ H 1 .
2 ι 6 5
OE
2 , 6 5
OH-CH o -CH-CH c
2, 6 5
OH
2 ι Ο 5
OH-CH 0 -CH-C ^ H
2 ι Ο 5
OH
2 , 6 5
OH-CH 0 -CH-C ^ H n
2, 6 5
OH
2 ι 6 5
OH.-CE 0 -CE-C ^ H ,.
2 ι 6 5
OH.
OH-CH 2 -CE-CgE 5
OH
OH-CEg-CE-CgH 5
OH
098187 10 04098 187 10 04
- 50 -- 50 -
λ-/ · LJ ·λ- / LJ
29 47-'29 47- '
2 ι 65
OH-CH 0 -CH-C ^ H
2 ι 65
OH
A09818/100AA09818 / 100A
G.Z. 29 ^72G.Z. 29 ^ 72
d. ι DR-CH 0 -CH-CrH
d. ι DR
2 ι ο S-CH-CH-CrH
2 ι ο S
-52 --52 -
'4 0 9 8 T 8 / 1 0 0 A'4 0 9 8 T 8/1 0 0 A
R CNR CN
NH-XNH-X
CZ. 29 472CZ. 29 472
409818/1004409818/1004
- 55 -- 55 -
O.Z. 29 47?O.Z. 29 47?
R ClTR ClT
UH-UH-
gelbreddish
yellow
gelbreddish
yellow
gelbreddish
yellow
3-CH
3
rotbluish tint
Red
J -H
J
rotbluish tint
Red
rotyellowish
Red
409818/1004409818/1004
- 54 -- 54 -
R CNR CN
NH-XNH-X
O.Z. £9 Vr;O.Z. £ 9 VR;
rotbluish tint
Red
rotbluish tint
Red
409818/1004409818/1004
- 55 -- 55 -
O.Z. 29 472O.Z. 29 472
OJ-M- N=N-^- NH-Y NH-XOJ-M- N = N - ^ - NH-Y NH-X
rotyellowish
Red
rotyellowish
Red
2 ι 6 5
OH-CH O -CH-C, H, -
2 ι 6 5
OH
rotyellowish
Red
2 , 6 5
OH-CH 0 -CH-CH
2, 6 5
OH
rotyellowish
Red
rotyellowish
Red
CH3 I j
CH 3
O.Z. 29 ^7?O.Z. 29 ^ 7?
2 ι 6 5
CH5 -CH 0 -CH-C ^ H
2 ι 6 5
CH 5
dt 05-CH 0 -CH-C ^ H 1 ,
German 05
Ι 3 /3
-CH-(CH0),-C-OH
d 5 \ CH- Μ
Ι 3/3
-CH- (CH 0 ), -C-OH
d 5 \
OHI s
OH
rotyellowish
Red
rotyellowish
Red
409818/1004409818/1004
O.Z. 29 ^72O.Z. 29 ^ 72
R CNR CN
N=N -e 7-NH-YN = N -e 7-NH-Y
■Τϊ NH-X■ Τϊ NH-X
2 ι ο 0
OH"GH λ""U Η ·· G A-tic
2 ι ο 0
OH
rotyellowish
Red
2 ι 0 5
OH-CH 0 -CH-CrH 1 . ·
2 ι 0 5
OH
rotyellowish
Red
2 ι 6 5
OH-CH 0 -CH-CrH, -
2 ι 6 5
OH
rotyellowish
Red
^l b 5
OH-CH 0 -CH-CrH
^ l b 5
OH
rotyellowish
Red
OH-CHg-CH-C 6 H 5
OH
rotyellowish
Red
OH-CH 2 -CH-C 6 H 5
OH
rotyellowish
Red
2 2 -CH -CH 0 -OH
2 2
409818/1004409818/1004
CZ. 29 «72 CZ. 29 «72
/125 1702/ 125 1702
chig rotyellow
chig red
CHj I J
CHj
-H1
-H
2 ι on -CH n -CH-CH 1 .
2 ι on
OH-Chg-CH-C 6 H
OH
chig rotyellow
chig red
chig rotyellow
chig red
409818/1004409818/1004
ORIGINAL INSPECTEDORIGINAL INSPECTED
O.ζ. 29 472O.ζ. 29 472
chig rotyellow
chig red
chig rotyellow
chig red
chig rotyellow
chig red
chig rot.yellow
chig red.
chig rotyellow
chig red
chig rotyellow
chig red
818/1004818/1004
- 60 -- 60 -
- 6o - O.Z. 29 472- 6o - OZ 29 472
409818/1004409818/1004
- 61 -- 61 -
υ ζ. ζ? 472υ ζ. ζ? 472
CNCN
N=N -V_V-N = N -V_V-
C1C1
NH-XNH-X
2 ι 6 1S-CH 9 -CH-CH
2 ι 6 1 p
OHI rf /
OH
2 1 65
OH-CH- 1 CH-CrH
2 1 65
OH
2 I r 1S -CH 0 -CH-C H
2 I r 1 S
-CHg-CH2-OH•
-CHg-CH 2 -OH
400818/1004 -CH -CH-OH
400818/1004
O.Z. 29 472O.Z. 29 472
Rι
R.
2 I b 5
OH-CH 0 -CH-C ^ H
2 I b 5
OH
OH-CHg-CH-C 6 H 5
OH
2 ι 6 5
OH-CH "-CH-C-; H_
2 ι 6 5
OH
409818/1004409818/1004
u.Z. 'd9 uZ 'd9
•~ \ wXl a j τ VJ ^ Y OXl J . WXl • ~ \ wXl a j τ VJ ^ Y OXl J. WXl
-- (CH 2 ) 3 -O- (CH 2 ) 4 -OH
-
^ Vj* Xl λ ^ ν Jl -π- "*" Λ-Ι* Xl j-t *■ * Vi* Χι *τ OTT OTT OTT öiOTX
^ Vj * Xl λ ^ ν Jl -π- "*" Λ-Ι * Xl jt * ■ * Vi * Χι * τ
!-CH-CH 2 -O-CH -CH-OH
!
409818/1004409818/1004
CZ. 29 472CZ. 29 472
R CNR CN
IH-YIH-Y
HH-XHH-X
blauchig
blue
chig blaurotsti
chig blue
blaureddish
blue
409818/10Oi409818 / 10Oi
ο.ζ. 29 472ο.ζ. 29 472
chig blau.rotsti
chig blue.
3 '-CH (η)
3 '
403818/1004403818/1004
- 66 -- 66 -
O.Z. 29 472O.Z. 29 472
S CNS CN
2" W2 "W.
HH-XHH-X
- 67 -- 67 -
409818/1004409818/1004
ο.ζ. 29ο.ζ. 29
CNCN
I-YI-Y
NH-XNH-X
lettrotvio
lett
violettRed
violet
violettRed
violet
violettRed
violet
409818/100'*409818/100 '*
- 68 -- 68 -
O.Z. 29 472O.Z. 29 472
2 ι b 5
OH—CH —— CH-C 1-4 -H
2 ι b 5
OH
violettRed
violet
(CH2)2-0CH5 - (CHg) 5 -0- (CH 2 ) 2 -0-
(CH 2 ) 2 -0CH 5
violettRed
violet
2 2 -CH-CH-OH
2 2
violettRed
violet
violettRed
violet
CH5 -CH 2 -CH-C 6 H 5
CH 5
violettRed
violet
3 7 -CH (η)
3 7
2 1 05
CH5 -CH 0 -CH-C ^ H 1 .
2 1 05
CH 5
violettRed
violet
409818/1004409818/1004
- 69 -- 69 -
O.Z. 29 472O.Z. 29 472
NH-XNH-X
110
11
CH3OC2H^OC-CHg-CHg-O
CH 3 OC 2 H ^ OC-CHg-CHg-
OH-CHg-CH-C 6 H 5
OH
CH3OC2H4OC-CH2-CH2-0
CH 3 OC 2 H 4 OC-CH 2 -CH 2 -
2 j 65-CH -CH-C ^ H
2 j 65
-C5H7Cn) J
-C 5 H 7 Cn)
OH-CHg-CH-C 6 H 5
OH
0.2. 290.2. 29
Aι
A.
CH,OC„Η,0C-CH0CH0-
2 c. 4 dc 0
CH, OC "Η, 0C-CH 0 CH 0 -
2 c. 4 dc
N
CH,0CoH,OC-CH0-CH0-
3 2 4 2 20
N
CH, 0C o H, OC-CH 0 -CH 0 -
3 2 4 2 2
CH5OC2H4OC-CH2-CH2-0
CH 5 OC 2 H 4 OC-CH 2 -CH 2 -
2 j 05 -CH O -CH-C> JL
2 y 05
3 2 4 2 4 'OH OC H 0-CC 0 H -
3 2 4 2 4
Oil·» ν ν v«** J" / "^LJ^1*1"' "" , ■ μ Ol TJ f \ ί ΓΚ ι TT ' C \ 1 ^ j ™ i TT
Oil · »ν ν v« ** J "/" ^ LJ ^ 1 * 1 "'""
CH3O(C2H4O)2S-C2H4-0
CH 3 O (C 2 H 4 O) 2 SC 2 H 4 -
ί ■ orange
ί ■
409818/1004409818/1004
_ 71 -_ 71 -
A R CNA R CN
NE-YNE-Y
A N-E-XA N-E-X
O.Z.O.Z.
chig gelbrotsti-.
chig yellow
chig gelbrotsti
chig yellow
D-Cl
D.
OH-CH 2 -CH-C 6 E 5
OH
2 ι op -CE 0 -CE-C ^ H ..
2 ι op
OE- (CE 2 ) 2 0 (CE,
OE
OH- (CEp 2 O (CH,
OH
ί orange
ί
2, .65
OH -CH 0 CH-Ci-H 1 . ■
2, .65
OH
409818/1004409818/1004
- 72 -- 72 -
u.Z. 29u.z. 29
22517C222517C2
2 ι ■ Oj
OH-CH 0 CH-CrHt-
2 ι ■ Oj
OH
chig gelbrotsti
chig yellow
OH-CH 0 CH-CrH 1 .
OH
chig gelbrotsti
chig yellow
2-CH 0 CH OH
2
2 I 6 5
OH-CH-CH-CrH 1 .
2 I 6 5
OH
gelbreddish
yellow
6 13-CONHCrH ,,
6 13
gelbreddish
yellow
gelbreddish
yellow
gelbreddish
yellow
409818/1004409818/1004
- 73 -- 73 -
O.Z. 29 4J2O.Z. 29 4J2
E CNE CN
NH-YNH-Y
NH-XNH-X
OH-CHg-CH-C 6 H 5
OH
£ f op
OH-CH 0 -CH-C ^ H-
£ f op
OH
te-te-
orangereddish
orange
- 74- 74
0.2. 290.2. 29
2,65
OH-CH 0 -CH-C, H_
2.65
OH
orangereddish
orange
d 1 0 5
OH-CH 0 -CH-C ^ H 1 ,
d 1 0 5
OH
orangereddish
orange
orangereddish
orange
2 \ b 5
CH5 -CH 0 -CI-O-CxH 1 .
2 \ b 5
CH 5
orangereddish
orange
Cm C* L·, fm. -CH 0 -CH 9 -O-CH 9 -CH 9 -OH
Cm C * L ·, fm.
- 75 -- 75 -
409816/1004409816/1004
O Z. 29O line 29
2 ι ο 5 ·-CH 0 -CH-C ^ H ,.
2 ι ο 5
2 b -CH
2 b
409818/1004409818/1004
- 76 -- 76 -
ο.ζ. 29ο.ζ. 29
CN R CNCN R CN
Br NH-XBr NH-X
OH —ΟΗλ — CH-Cz-Hj-
OH
^l op
OH-CH 0 -CH-C J3_
^ l op
OH
818/1004818/1004
2251722517
O,ζ. 29O, ζ. 29
2 I D 5
OH-.CHo-CH-C ^ H 1 .
2 ID 5
OH
2 , 0 5
OH-.CH n -OH-C JSf
2, 0 5
OH
2 ι ο 3
CH3 . ;-CHo-CE-O-Cv-H 1 .
2 ι ο 3
CH 3 . ;
- 78 -- 78 -
Ο-Ζ. 21 472Ο-Ζ. 21 472
2 1 b 5
OH-CH 0 -CH-CtH 1 .
2 1 b 5
OH
2 ι 6 5
OH-CH 0 -CH-C ^ H 1 .
2 ι 6 5
OH
409818/10CU409818 / 10CU
- 79,- 79.
O.Z. 29O.Z. 29
CN . R CN Cl-^ Λ- Ν=Ν-7χ-\_ΝΗ-ΥCN. R CN Cl- ^ Λ- Ν = Ν-7 χ - \ _ ΝΗ-Υ
Cl NH-XCl NH-X
OH-CHg-CH-CgH-
OH
2 I op
OH -CH 0 -CH-C ^ H 1 -
2 I op
OH
4098 18/10044098 18/1004
- 80 -- 80 -
O.Z. 29 4'.'2O.Z. 29 4 '.' 2
2 ι 6 5
OH-CH 0 -CH-Cz-Hj-
2 ι 6 5
OH
έ ι 6 5
OH-CH O -CH-C, H C
έ ι 6 5
OH
if- (CHg) 5 -O- (CHg) 2 -OC 6 H 5
if
OH, -CHg-CH-OC 6 H 5
OH,
-CHg-CHg-OCH5 i1
-CHg-CHg-OCH 5 i
- Θ1 -- Θ1 -
409818/1004409818/1004
O.Z. 2.9 472OZ 2.9 472
OH2 1 6 5
OH
-O2XIj- / 1 DD
-O 2 XIj-
- 82 -- 82 -
409818/1004409818/1004
O.Z. 29 472 OZ 29 472
CN R CN Br // \\ N=N -/~^- NH-YCN R CN Br // \\ N = N - / ~ ^ - NH-Y
NH-XNH-X
2 ι op
OH—CH, * - CH-G ^ He
2 ι op
OH
2 ι 05
OH-CH_-CH-C, H C
2 ι 05
OH
409818/1004409818/1004
ο.ζ. 29ο.ζ. 29
-•84 -- • 84 -
409818/1004409818/1004
O.Z. 29 472O.Z. 29 472
Dir. R FarbtonDir. R hue
-C5H7 (n)-C 5 H 7 (n)
-C5H7 (n)-C 5 H 7 (n)
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
-H-H
.(CH2)3-O-(CH2)4-OH. (CH 2 ) 3 -O- (CH 2 ) 4 -OH
CH0-CH-C^H.. OHCH 0 -CH-C ^ H .. OH
/,-CH- C^ 2 ι /, - CH- C ^ 2 ι
OHOH
-(CH2)2-O-(CH2)2-OCHO CH2-CH2-OH- (CH 2 ) 2 -O- (CH 2 ) 2 -OCHO CH 2 -CH 2 -OH
C2H5 C 2 H 5
CH2-CH2-CH2-OHCH 2 -CH 2 -CH 2 -OH
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
gelbyellow
gelbyellow
gelbyellow
gelbyellow
gelbyellow
-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH
gelbyellow
-CH2-CH2-OCH5 -CH 2 -CH 2 -OCH 5
-(CH9 L-O-(CHj0-O-COCH- -CH9-CH9-OCH- (CH 9 LO- (CHj 0 -O-COCH- -CH 9 -CH 9 -OCH
-(CH2)5-O-(CH2)2-O-C6H5 -CH2-CH2-OCH3 - (CH 2 ) 5 -O- (CH 2 ) 2 -OC 6 H 5 -CH 2 -CH 2 -OCH 3
gelbyellow
gelbyellow
gelbyellow
- 85 -- 85 -
409818/100A409818 / 100A
ζ. 29ζ. 29
COOCH, E CN Cl -VM- JST=IT-Z^X-HH-YCOOCH, E CN Cl -VM- JST = IT-Z ^ X-HH-Y
Cl 3JH-XCl 3JH-X
2. ι 0 5
OH-CH 0 -CH-C ^ H 1 .
2. ι 0 5
OH
981871004981871004
- 86 -- 86 -
O.Z. 29O.Z. 29
bis orangegolden yellow
to orange
bis orangegolden yellow
to orange
d j Op -CH 0 -CH-C ^ H ,.
d j Op
- 87 -- 87 -
4 0 98 18./10 044 0 98 18./10 04
O.Z- 29 '+72O.Z- 29 '+72
— LiIl0-OIl0-O £ JH. J-
ά cop OTT OTT O TT
- LiIl 0 -OIl 0 -O £ JH. J-
ά cop
2 j Dp-CH 0 -CH-C ^ Hj-
2 j Dp
- 88 -- 88 -
4098 18/10 0.44098 18/10 0.4
0.2. 290.2. 29
ClCl
COOCH2 R CN / 3 y/COOCH 2 R CN / 3 y /
NH-XNH-X
409818/1004409818/1004
-89--89-
O.Z. 29 '+72O.Z. 29 '+72
bis orangegolden yellow
to orange
bis orangegolden yellow
to orange
-CH0-CH-C^H1.-τ.
-CH 0 -CH-C ^ H 1 .
£i ι Oy -CH 0 -CH-C, ^
£ i ι Oy
21 c. y -CH 0 -CH 0 -OCH. ■
21 c. y
409818/Ϊ004'409818 / Ϊ004 '
- 90 -- 90 -
0..I. 2Q *7 0..I. 2Q * 7
2 , ο 5
CH,-CH 0 -CH-C ^ Hc
2, ο 5
CH,
CH3 -CH 2 -CH-C 6 H 5
CH 3
d \ DP
OH-CH 0 -CH-C, H c
d \ DP
OH
409818/1004409818/1004
- 91 - "■ - 91 - "■
22517Ö222517Ö2
O.Z. 29 OZ . 29
ίΐ/7Γ>ίΐ / 7Γ>
CNCN
HN-XHN-X
OH-CH 0 -CH-C ^ H 1 .
OH
rotbluish tint
Red
2 ι 6 5
OH-CH 0 -CH-C ^ H 1 -
2 ι 6 5
OH
rotbluish tint
Red
OH-CHg-CH-C 6 H 5
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
409818/1004409818/1004
_ 92 -_ 92 -
ο. ζ. 29 472ο. ζ. 29 472
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
OH-CH 2 -CH-C 6 H 5
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
2 ι OO
OH-CH 9 -CH-C ^ H-
2 ι OO
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
dc c. Op-CH 0 -CH 0 -O-COCH 0 -OC ^ Hc
dc c. Op
rotbluish tint
Red
ar -CH 2 -CH 2 -O-CII 3
ar
rotbluish tint
Red
40981 8/ 1 Q-CHg-CHg-O-CHg-CHg-OCHO
40981 8/1 Q
rotbluish tint
Red
- 95 -- 95 -
0.2. 29 0.2. 29
E QM E QM
Cl HN-XCl HN-X
d j ο 7
OH-CH n -CH-C λΗγ
d j ο 7
OH
rotbluish-resistant
Red
OH-CHg-CH-CgH 5
OH
rotbluish tint
Red
OH; -CHg-CH-GgHc
OH
rot; bluish tint
Red
rotbluish tint
Red
^V V,* Π j-t y'^^*w^\ ν/JX λ y ^· KJ0^Vj f Σχ, p»
"V ^ Gt 0' ^ ι ^ TX ι Λ r OTT 1 Λ ^ 1 'TT
^ VV, * Π jt y '^^ * w ^ \ ν / JX λ y ^ · KJ 0 ^ Vj f Σχ, p »
"V ^ Gt 0 '^
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
4OS810/1Q(H4OS810 / 1Q (H.
CZ. 29 472CZ. 29 472
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
OH-CH 2 -CH-C 6 H 5
OH
rotbluish tint
Red
rotbluish tint
Red
OH-CHg-CH-C 6 H 5
OH
rotbluish tint
Red
rot ■ bluish tint
red ■
■ rot ;■ bluish tint
■ red; ■
CC C D 5 -CH 0 -CH 0 -O-COCH 0 -OC ^ H 1 .
CC C D 5
rot" ; lv!: bluish tint
red "; lv !:
/rotbluest ichig:
/Red
rotbluish
Red
40 98 18/ 100 440 98 18/100 4
CZ. 29 4-72CZ. 29 4-72
NO2 if -CNNO 2 if -CN
' \\_ N=N-A^- NH-Y ~ )"Ν'\\ _ N = N-A ^ - NH-Y ~) "Ν
Br HIT-XBr HIT-X
2 1 05
OH—CH, .- CH-C / fHi-
2 1 05
OH
rotbluish tint
Red
2 ι 6 5
OH* ™ Οχι, -, ■ · CH ^ C / Ήγ-
2 ι 6 5
OH
rotbluish tint
Red
2 1 05
OH—CH —— CH-C 1 H 1 .
2 1 05
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
A0981 8/1QOAA0981 8 / 1QOA
O. Z. 29 VT2 OZ 29 VT2
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
2 1 05
OH-CH 0 -CH-CrH 1 .
2 1 05
OH
rotbluish tint
Red
rotbluish tint
Red
2 ι op
OH-CH-CH-C ^ H c
2 ι op
OH
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
ά i do? -CH 0 -CH 0 -O-COCH 0 -O-CrH ..
ά i do?
rotbluish tint
Red
rotbluish tint
Red
rotbluish tint
Red
4098 1 8/ 1OCU4098 1 8 / 1OCU
- 97 -- 97 -
22512251
O-Z^ 29O-Z ^ 29
TaIa eileTaIa hurry
Br E CIiBr E CIi
IEEE-YIEEE-Y
"S HS-X "S HS-X
c ο i 4- (CH 0 ), - 0- (CB 0 ) - OH
c ο i 4
48881:8/100448881: 8/1004
fafcell« 32fafcell «32
ItIt
29 47229 472
E CIE CI
HH-XHH-X
409818/108 4409818/108 4
22bf70222bf702
C-Z. 29 kl?. CZ. 29 kl ?.
CN RZCN RZ
NHYNHY
NHXNHX
OHCHpCH-C / rH (-
OH
40981 8./ 100440981 8th / 1004
Claims (4)
D-N=N-Q-NH-YRZ
DN = NQ-NH-Y
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722251702 DE2251702B2 (en) | 1972-10-21 | 1972-10-21 | Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use |
| CH321773A CH596263A5 (en) | 1972-03-10 | 1973-03-05 | |
| 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 | |
| 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 | |
| IT48707/73A IT979789B (en) | 1972-03-10 | 1973-03-09 | AZOCOLORANTS WITH 2, 6 DIAMMINOPYRIDINE DERIVATIVES AS COPULATION COMPONENTS |
| NL7303378A NL7303378A (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 |
| JP48027651A JPS6139347B2 (en) | 1972-03-10 | 1973-03-10 | |
| CH1472773A CH601427A5 (en) | 1972-10-21 | 1973-10-18 | |
| DD17417773A DD107067A5 (en) | 1972-10-21 | 1973-10-19 | |
| FR7337409A FR2203853B1 (en) | 1972-10-21 | 1973-10-19 | |
| IT5322373A IT997769B (en) | 1972-10-21 | 1973-10-19 | DYES FROM DISPERSION OF SERIES 2, 6, PYRIDINE DIAMOND |
| GB4876573A GB1438584A (en) | 1972-10-21 | 1973-10-19 | Disperse azo dyes of the 2,6-diaminopyridine series |
| CS725573A CS177151B2 (en) | 1972-10-21 | 1973-10-22 | |
| BE136923A BE806349A (en) | 1972-10-21 | 1973-10-22 | DISPERSED DYES OF THE 2,6- DIAMINOPYRIDINE SERIES |
| JP11800673A JPS4974719A (en) | 1972-10-21 | 1973-10-22 | |
| 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 |
|---|---|---|---|
| DE19722251702 DE2251702B2 (en) | 1972-10-21 | 1972-10-21 | Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2251702A1 true DE2251702A1 (en) | 1974-05-02 |
| DE2251702B2 DE2251702B2 (en) | 1976-11-18 |
Family
ID=5859674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722251702 Granted DE2251702B2 (en) | 1970-12-19 | 1972-10-21 | Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4974719A (en) |
| BE (1) | BE806349A (en) |
| CH (1) | CH601427A5 (en) |
| CS (1) | CS177151B2 (en) |
| DD (1) | DD107067A5 (en) |
| DE (1) | DE2251702B2 (en) |
| FR (1) | FR2203853B1 (en) |
| GB (1) | GB1438584A (en) |
| IT (1) | IT997769B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146535A (en) * | 1975-10-29 | 1979-03-27 | Basf Aktiengesellschaft | Azo dyes having a 3-cyano- or 3-carbamoyl-2,6-diamino-pyridine coupling component |
| EP0042486A1 (en) * | 1980-06-06 | 1981-12-30 | BASF Aktiengesellschaft | Method of colouring coating-substances, organic solvents and mineral-oil products, and dyestuffs |
| JPS62263259A (en) * | 1986-05-03 | 1987-11-16 | バスフ アクチェン ゲゼルシャフト | Diaminopyridine azo dye having acyloxy group |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3330155A1 (en) * | 1983-08-20 | 1985-03-07 | Basf Ag, 6700 Ludwigshafen | ISOTHIAZOLAZO DYES |
| JP3165745B2 (en) * | 1992-07-13 | 2001-05-14 | ダイスタージャパン株式会社 | Monoazo disperse dyes and mixtures thereof |
-
1972
- 1972-10-21 DE DE19722251702 patent/DE2251702B2/en active Granted
-
1973
- 1973-10-18 CH CH1472773A patent/CH601427A5/xx not_active IP Right Cessation
- 1973-10-19 GB GB4876573A patent/GB1438584A/en not_active Expired
- 1973-10-19 DD DD17417773A patent/DD107067A5/xx unknown
- 1973-10-19 IT IT5322373A patent/IT997769B/en active
- 1973-10-19 FR FR7337409A patent/FR2203853B1/fr not_active Expired
- 1973-10-22 BE BE136923A patent/BE806349A/en unknown
- 1973-10-22 JP JP11800673A patent/JPS4974719A/ja active Pending
- 1973-10-22 CS CS725573A patent/CS177151B2/cs unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146535A (en) * | 1975-10-29 | 1979-03-27 | Basf Aktiengesellschaft | Azo dyes having a 3-cyano- or 3-carbamoyl-2,6-diamino-pyridine coupling component |
| EP0042486A1 (en) * | 1980-06-06 | 1981-12-30 | BASF Aktiengesellschaft | Method of colouring coating-substances, organic solvents and mineral-oil products, and dyestuffs |
| JPS62263259A (en) * | 1986-05-03 | 1987-11-16 | バスフ アクチェン ゲゼルシャフト | Diaminopyridine azo dye having acyloxy group |
| JPH07108954B2 (en) | 1986-05-03 | 1995-11-22 | バスフ アクチェン ゲゼルシャフト | Diaminopyridine azo dye having an acyloxy group |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2203853B1 (en) | 1977-08-19 |
| JPS4974719A (en) | 1974-07-18 |
| IT997769B (en) | 1975-12-30 |
| CH601427A5 (en) | 1978-07-14 |
| BE806349A (en) | 1974-04-22 |
| DD107067A5 (en) | 1974-07-12 |
| FR2203853A1 (en) | 1974-05-17 |
| GB1438584A (en) | 1976-06-09 |
| DE2251702B2 (en) | 1976-11-18 |
| CS177151B2 (en) | 1977-07-29 |
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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 | ||
| EHV | Ceased/renunciation |