DE2251702B2 - Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use - Google Patents

Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use

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Publication number
DE2251702B2
DE2251702B2 DE19722251702 DE2251702A DE2251702B2 DE 2251702 B2 DE2251702 B2 DE 2251702B2 DE 19722251702 DE19722251702 DE 19722251702 DE 2251702 A DE2251702 A DE 2251702A DE 2251702 B2 DE2251702 B2 DE 2251702B2
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DE
Germany
Prior art keywords
chj
red
orange
cii
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
DE19722251702
Other languages
German (de)
Other versions
DE2251702A1 (en
Inventor
Johannes Dr.; Lamm Günther Dr.; 6700 Ludwigshafen Dehnert
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BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19722251702 priority Critical patent/DE2251702B2/en
Priority to CH321773A priority patent/CH596263A5/xx
Priority to US05/338,859 priority patent/US4042578A/en
Priority to DD169311A priority patent/DD106192A5/xx
Priority to SU1891749A priority patent/SU521848A3/en
Priority to IT48707/73A priority patent/IT979789B/en
Priority to GB1140873A priority patent/GB1422650A/en
Priority to NL7303378A priority patent/NL7303378A/xx
Priority to FR7308567A priority patent/FR2187857B1/fr
Priority to JP48027651A priority patent/JPS6139347B2/ja
Priority to CH1472773A priority patent/CH601427A5/xx
Priority to IT5322373A priority patent/IT997769B/en
Priority to GB4876573A priority patent/GB1438584A/en
Priority to DD17417773A priority patent/DD107067A5/xx
Priority to FR7337409A priority patent/FR2203853B1/fr
Priority to JP11800673A priority patent/JPS4974719A/ja
Priority to CS725573A priority patent/CS177151B2/cs
Priority to BE136923A priority patent/BE806349A/en
Publication of DE2251702A1 publication Critical patent/DE2251702A1/en
Priority to US05/711,863 priority patent/USRE29640E/en
Publication of DE2251702B2 publication Critical patent/DE2251702B2/en
Granted legal-status Critical Current

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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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Pyridine Compounds (AREA)

Description

Die hrtindung beinllt Farbstoffe der allgemeinen Formel I The hardening includes dyes of the general formula I.

N
NH-XN
NH-X

-NH-Y-NH-Y

in der D der Rest einer Diazokomponente der Benzol-, Diphenylenoxid-, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe, R Wasserstoff, C,- bis C7-Alkyl oder Phenyl, X und Y Wasserstoff, C,- bis Cs-Alkyl, durch Hydioxy, C1- bis C8-Alkoxy, Phenoxy, Phenoxyäthoxy, Benzyloxy, Formyloxy, Acetoxy, Chloracetoxy, Äthoxycarbonyloxy, Acetoacetoxy oder Phenoxyacetoxy substituiertes C2- bis Cs-Alkyl. Cyclohexyl, Phenyl-C,- bis C4-alkyl, /i-Phenyl-j.'-hydroxyäthyl, in which D is the remainder of a diazo component of the benzene, diphenylene oxide, benzthiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series, R is hydrogen, C 1 to C 7 alkyl or phenyl, X and Y is hydrogen, C 1 to C s -alkyl, C 2 to C s -alkyl substituted by hydroxy, C 1 - to C 8 -alkoxy, phenoxy, phenoxyethoxy, benzyloxy, formyloxy, acetoxy, chloroacetoxy, ethoxycarbonyloxy, acetoacetoxy or phenoxyacetoxy . Cyclohexyl, phenyl-C, - to C 4 -alkyl, /i--phenyl-j.'-hydroxyethyl,

CH,CH,

CH-CH1CH1 CH-CH 1 CH 1

OHOH

gegebenenfalls durch Chlor. Methyl, Methoxy oder Äthoxy substituiertes Phenyl.optionally by chlorine. Methyl, methoxy or ethoxy substituted phenyl.

(CH2)2O(CH2)2OH
(CH2).,O(CH2)6OH(CH 2 ) 2 O (CH 2 ) 2 OH
(CH 2 )., O (CH 2 ) 6 OH

(CH2 ).,O(CH2)4OH
(CH2I3OC2H4OCH,(CH 2 )., O (CH 2 ) 4 OH
(CH 2 I 3 OC 2 H 4 OCH,

(CHj)3(OC2H4I2 OCH3 (CHj) 3 (OC 2 H 4 I 2 OCH 3

(CH,)2 O(CH,)2OAcyl(CH,) 2 O (CH,) 2 O acyl

(CH2 ).,O(CH, )4 OAcyl(CH 2 )., O (CH,) 4 OAcyl

CH2CH - C6H5 CH 2 CH - C 6 H 5

OAcylOAcyl

und Z Cyan oder Carbamoyl sind, wobei Acyl CHO, COCH3, COCH2Cl, COCH2COCH3. C(X^H2OC6H5. COOC2H5, CONHCH3 oder CONHC6H5 ist, sowie ein Verfahren zu deren Herstellung und ihre Verwendung zum Färben von Textilmaterial.and Z are cyano or carbamoyl, where acyl is CHO, COCH 3 , COCH 2 Cl, COCH 2 COCH 3 . C (X ^ H 2 OC 6 H 5. COOC 2 H 5 , CONHCH 3 or CONHC 6 H 5 , as well as a process for their production and their use for dyeing textile material.

Gegenüber nächst vergleichbaren, aus der DT-PS 20 62 717 bekannten Farbstoffen haben die erfindungsgemäßen Farbstoffe Vorteile im Ziehvermögen auf Polyester-, Polyamid- und Cellulose-^1 ,-acetat-CJewebe. Opposite closest comparable, known from DT-PS 20 62 717 dyes are dyes advantages of the invention in drawing ability on polyester, polyamide and cellulose ^ 1, acetate CJewebe.

Als Substituenlen für die Reste D der Diazokomponenlcn sind beispielsweise zu nennen:As substituents for the radicals D of the diazo components include, for example:

In der Benzolrcihe: Chlor, Brom, Nitro, Cyan, Trifluormelhyl, Mcthylsulfonyl, Äthylsulfonyl, Phenylsulfonyl, Carbomelhoxy, Carbobutoxy. Carbo-,;-melhoxyälhoxy, C'arbo-/)'- hydroxyälhoxy. gegebenenfalls N-ITH)HO- oder N-disubstituiertes Carbon- oder Suli'onamid. Methyl. Äthyl. Melhoxy und Äthoxy. In the benzene line: chlorine, bromine, nitro, cyano, Trifluoromelhyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, Carbomelhoxy, carbobutoxy. Carbo -,; - melhoxyälhoxy, C'arbo - /) '- hydroxyälhoxy. possibly N-ITH) HO- or N-disubstituted carbon- or sulfonamide. Methyl. Ethyl. Melhoxy and ethoxy.

N-Siibslituenlen der Carbon- oder Sulfonamide sind dabei /.. B. Methyl. Äthyl. Propyl. Butyl. ,'-Hydroxyälhyl. ;■ - Hydroxypiopyl. ,; - Methoxyälhyl. y-Methoxypropyl oder --Älluixypiopyl sowie das Pyrrolidid, Piperidid oder Morpholid.N-Siibslituenlen of the carbon or sulfonamides are included / .. B. methyl. Ethyl. Propyl. Butyl. , '- hydroxyethyl. ; ■ - hydroxypiopyl. ,; - methoxyethyl. y-methoxypropyl or --Älluixypiopyl as well as that Pyrrolidide, piperidide or morpholide.

In der Azobenzolreihe: Chlor, Brom, Nitro, Cyan. Methyl, Hydroxy, Äthyl. M_'ihoxy oder Äthoxy. In den heterocyclischen Reihen: Chlor, Brom, Nitro. Cyan, Methyl. Äthyl, Phenyl. Methoxy, Äthoxy, Methylmercapto, //-Carbomethoxyäthylmercapto, ß-Carboäthoxyäthylmercapto, Carbomethoxy, Carboäthoxy. Acetyl. Methylsulfonyl oder Äthylsulfonyl.In the azobenzene series: chlorine, bromine, nitro, cyano. Methyl, hydroxy, ethyl. M_'ihoxy or ethoxy. In the heterocyclic series: chlorine, bromine, nitro. Cyano, methyl. Ethyl, phenyl. Methoxy, ethoxy, methyl mercapto, // - carbomethoxyethyl mercapto, ß-car boäthoxyäthylmercapto, 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. ο-, m- oder p-Nitroanilin, o-, m- oder p-Cyanilin, 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, 2-MethyI-4-nitroanilin. 2-Methoxy-4-nitroanilin, 4-Chlor-2-nitroanilin, 4-Methyl-2-nitroanilin, 4-Methoxy-2-nitroanilin, 1 -Amino^-trifluormethyl^-chlorbenzol, 2 - Chlor - 5 - aminobenzonitril, 2 - Amino-5 - chlorbenzonitril. 1 -Amino - 2 - nitrobenzol - 4 - sulfonsäure-n-butylamid oder -/>'-methoxyäthy!amid. 2.4-Dinitroanilin. 2,4-Dinitro-6-chloranilin. 2,4-Dinitro - 6 - bromanilin, 2,4 - Dinitro - 6 - cyananilin. 1 -Amino^^-dinitrobenzol-o-methylsulfon. 2.6-Diehlor - 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, I -Aminobenzol-4-methylsulfon. 1 - Amino - 2,6 - dibrom - benzol - 4 - methylsulfon, 1 -Amino-2,6-dichlorbenzol-4-methylsulfon. 1 - Amino - 2,4 - dinitrobenzol - 6 - carbonsäure - methylester oder -/i-methoxyäthylester, 3,5-Dichloranthranilsäure-propylesler, S^-Dibrom-anthranilsäure-^-methoxyäthylester, N-Acetyl-p-phenylendiamin, 4-Aminoacetophenon, 4- oder 2-Amino-benzophenon, 2- und 4-Aminodiphenylsulfon, 2-, 3- oder 4-Aminobenzoesäure-methylester, -äthylester, -propylester, -butylester, -isobutylester, -^-methoxyäthylester, -/i-äthoxyäthylester, -methyl - diglykolester, -äthyl - diglykolester, -methyl - triglykolesttr, -äthyltriglykolester, -/i-hydroxyäthylester, -/i-acetoxy-äthylester, -ß-(fi'-hydroxy - äthoxy) - äthylester, -ß - hydroxy - propylester, -;■ - hydroxy - propylester, -<n - hydroxy - butylester, -nt - hydroxy - hexylester, 5 - Nitro - anthranilsäuremethylester, -isobutylester, -methyl - diglykolester, -/i-methoxy-äthylester, -/i-butoxy-äthylester, -/i-acetoxy-äthylester, 3-oder 4-Aminophthalsäure-, 5-Aminoisophthalsäure- oder Amino - terephthalsäure - dimethylester, -diäthylester, -dipropylester, -dibutylester, 3- oder 4-Aminobenzoesäure-amid, -methylamid, -propylamid, -butylamid, -isobutylamid, -cyclohexylamid, -ß-äthyl-hexylamid, -y-methoxypropylamid, -)'-äthoxy-propylamid, 2-, 3- oder 4-Aminobenzoesäure-dimethylamid, -diäthylamid, -pyrrolidid, -morpholid, N - methyl -N- β- hydroxy - äthylamid,The remainder D is derived in detail z. B. of the following amines: aniline, o-, m- or p-toluidine. ο-, m- or p-nitroaniline, o-, m- or p-cyaniline, 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, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline, 1-amino ^ -trifluoromethyl ^ -chlorobenzene, 2 - chloro - 5 - aminobenzonitrile, 2 - amino-5 - chlorobenzonitrile. 1-amino-2-nitrobenzene-4-sulfonic acid-n-butylamide or - />'- methoxyethy! Amide. 2,4-dinitroaniline. 2,4-dinitro-6-chloroaniline. 2,4-dinitro-6-bromaniline, 2,4-dinitro-6-cyananiline. 1 -Amino ^^ - dinitrobenzene-o-methylsulfone. 2.6-diehlor-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, I-aminobenzene-4-methylsulfone. 1 - amino - 2,6 - dibromo - benzene - 4 - methyl sulfone, 1 - amino-2,6-dichlorobenzene-4-methyl sulfone. 1 - Amino - 2,4 - dinitrobenzene - 6 - carboxylic acid methyl ester or - / i-methoxyethyl ester, 3,5-dichloroanthranilic acid propylsler, S ^ -dibromanthranilic acid - ^ - methoxyethyl ester, N-acetyl-p-phenylenediamine, 4 -Aminoacetophenone, 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, - ^ - methoxyethyl ester, - / i-ethoxyethyl ester, -methyl-diglycol ester, -ethyl-diglycol ester, -methyl-triglycol ester, -ethyl triglycol ester, - / i-hydroxyethyl ester, - / i-acetoxy-ethyl ester, -ß- (fi'- hydroxy - ethoxy) - ethyl ester , -ß - hydroxy - propyl ester, -; ■ - hydroxy - propyl ester, - <n - hydroxy - butyl ester, - n - hydroxy - hexyl ester, 5 - nitro - anthranilic acid methyl ester, - isobutyl ester, - methyl - diglycol ester, - / i-methoxy -ethyl ester, - / i-butoxy-ethyl ester, - / i-acetoxy-ethyl ester, 3- or 4-aminophthalic acid, 5-aminoisophthalic acid or amino - terephthalic acid - dimethyl ester, diethyl ester, dipropyl ester he, dibutyl, 3- or 4-aminobenzoic acid amide, -methylamide, -propylamid, butylamide, isobutylamide, -cyclohexylamid, -SS- ethyl-hexylamide, -y-methoxypropylamid, -) '- ethoxy-propylamide, 2 -, 3- or 4-aminobenzoic acid dimethylamide, diethylamide, pyrrolidide, morpholide, N - methyl -N- β- hydroxy - ethylamide,

5 - Amino - isophthalsäurediamid, -bis - )· - methoxypropylamid, Aminoterephthalsäure-bis-diäthylamid, 3- oder 4-Amino-phthalsäure-imid, -/i-hydroxyäthylamid-, )'-hydroxy-propylamid, 3-Amino-6-nitrophthalsäurc - // - hydroxy - äthylamid, 2-, 3- oder 4 - Aminobenzosulfonsäure - dimethylamid, -diäthylamid, -pyrrolidid, -morpholid, Methylsulfonsäure-2-, -3'- oder 4'-amino-phenylester, Äthylsulfonsäure-2'-. -3'- oder -4'-amino-phenylester, Butylsulfonsäure-2'-. -3'- oder -4'-aminophenylester, Benzolsulfonsiiure-2'-. -3- oder4'-aminophenylester, 2-Amino-anthrachinon. 1-Amino-4-chlor-anthrachinon, 3- oder 4-Aminodiphcnylcnoxid, 2 - Amino - benzthiazol, 2 - Amino-5 - Amino - isophthalic acid diamide, - bis -) - methoxypropylamide, aminoterephthalic acid bis-diethylamide, 3- or 4-amino-phthalic acid-imide, - / i-hydroxyethylamide-,) '- hydroxy-propylamide, 3-amino-6 -nitrophthalic acid - // - hydroxy - ethyl amide, 2-, 3- or 4 - aminobenzosulfonic acid - dimethyl amide, diethyl amide, pyrrolidide, morpholide, methylsulfonic acid 2-, -3'- or 4'-aminophenyl ester, ethyl sulfonic acid 2'-. -3'- or -4'-aminophenyl ester, butylsulfonic acid 2'-. -3'- or -4'-aminophenyl ester, benzenesulfonic acid-2'-. -3- or 4'-aminophenyl ester, 2-amino-anthraquinone. 1-Amino-4-chloro-anthraquinone, 3- or 4-aminodiphynylcnoxide, 2 - amino - benzothiazole, 2 - amino

6 - carbonsäure - methylester - benzthiazol, 2 - Amino-6 - carboxylic acid methyl ester - benzthiazole, 2 - amino

6 - methyl - sulfonyl - benzthiazol, 2 - Amino - 6 - cyanbenzthiazcl, 2 - Amino - 6 - nitro - benzthiazol. 5,6- oder 6.7-Dichlor-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,l-benzisothiazol, 2-Aminothiazol, 2-Amino-5-nitrothiazol, 2-Amino-4-methy!-thiazr>l-5-carbonsäure - äthylester, 2 - Amino - 4 - methyl - 5 - acetylthia7ol, 2-Amino-3-cyan-4-methyl-thiophen-5-carbonsäureester, 2- Phenyl-5-amino-1.3.4- thiadiazol. 3 - Methylmercapto - 5 - amino - 1.2.4 - thiadiazol. 3-/)-Carbomethoxy-äthylmercapto-5-amino-1.2.4-thiadiazol. 6 - methyl - sulfonyl - benzothiazole, 2 - amino - 6 - cyanobenzothiazole, 2 - amino - 6 - nitro - benzothiazole. 5,6- or 6.7-dichloro-2-aminobenzothiazole. 4-amino-5 - bromo - 7 - nitro - 1,2 - benzisothiazole. 3 - Amino-5 - nitro - 2,1 - benzisothiazole, 3 - Amino - 5 - nitro-7-bromo-2, l-benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-methyl-thiazole> 1-5-carboxylic acid - ethyl ester, 2 - amino - 4 - methyl - 5 - acetylthia7ol, 2-amino-3-cyano-4-methyl-thiophene-5-carboxylic acid ester, 2-phenyl-5-amino-1.3.4-thiadiazole. 3 - methyl mercapto - 5 - amino - 1.2.4 - thiadiazole. 3 - /) - Carbomethoxy-ethylmercapto-5-amino-1,2,4-thiadiazole.

Geeignete Diazokomponenten der Aminoazobenzolreihe sind beispielsweise:Suitable diazo components of the aminoazobenzene series are, for example:

4-Aminoazobenzol.4-aminoazobenzene.

2 ',S-Dimethyl^aminoazobenzol,2 ', S-dimethyl ^ aminoazobenzene,

3'.2-DimethyI-4-amίnoazobenzol.3'.2-Dimethyl-4-aminoazobenzene.

2.5-Dimethyl-4-aminoazobcnzol.2,5-dimethyl-4-aminoazobenzene.

2-Mcthyl-5-methoxy-4-aminoazobenzol.2-methyl-5-methoxy-4-aminoazobenzene.

2-Methyl-4',5-dimethoxy-4-aminoazobcn/ol.2-methyl-4 ', 5-dimethoxy-4-aminoazobcn / ol.

4'-Chlor-2-methyl-5-methoxy-4-aminoazobenzol.4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene.

4'-Nitro-2-methyl-5-methoxy-4-aminoazobcn/t)l.4'-Nitro-2-methyl-5-methoxy-4-aminoazobcn / t) l.

4 -Chlor-2-methyl-4-aminoazobenzol.4-chloro-2-methyl-4-aminoazobenzene.

2,5-Dimcthoxy-4-aminoazobenzol.2,5-dimethyl-4-aminoazobenzene.

4'-Chlor-2,5-dimethoxy-4-aminoazobenzol.4'-chloro-2,5-dimethoxy-4-aminoazobenzene.

4'-Nitro-2,5-dimcthoxy-4-aminoazobenzol.4'-nitro-2,5-dimethoxy-4-aminoazobenzene.

4-Chlor-2,5-dimethyl-4-aminoazoben/ol.4-chloro-2,5-dimethyl-4-aminoazoben / ol.

4-Methoxy-2.5-dimethyl-4-aminoazobcnzol.4-methoxy-2,5-dimethyl-4-aminoazobenzene.

4-Nitro-4-aminoazobcnzol.4-nitro-4-aminoazobenzene.

3.5-Dibrom-4-aminoazobenzol.3.5-dibromo-4-aminoazobenzene.

2.3'-Dichlor-4-aminoazobenzol.2.3'-dichloro-4-aminoazobenzene.

^-Mcthoxy^-aminoazobenzol.^ -Methoxy ^ -aminoazobenzene.

4'-Hydroxy-2'-mcthyl-4-aminoazobenzol.4'-Hydroxy-2'-methyl-4-aminoazobenzene.

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, Phcnylpropyl. Phenylbutyl. gegebenenfalls durch Chlor, Methyl, Methoxy oder Äthoxy substituiertes Phenyl sowie Polyalkoxyalkyl. Hydroxypolyalkoxyalkyl, Alkanoyloxyalkyl oder Alkoxycarbonylalkyl der nachstehend genannten Art.The radicals X and Y, which are identical or different can be, in addition to hydrogen, for example, alkyl with 1 to 8 carbon atoms, optionally through Hydroxy. Alkoxy with 1 to 8 carbon atoms. Phenoxy. Phenoxyethoxy or benzyloxy substituted alkyl. Cyclohexyl, benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl. Phenylbutyl. possibly phenyl substituted by chlorine, methyl, methoxy or ethoxy and polyalkoxyalkyl. Hydroxypolyalkoxyalkyl, Alkanoyloxyalkyl or alkoxycarbonylalkyl of the type mentioned below.

Kinzelnc Reste X und Y sind beispielsweise die Alkylresle Methyl, Äthyl, Propyl, Butyl, die Hydroxyalkylreste /i-Hydroxyäthyl oder -propyl. ;-Hyilroxypropyl. c-Hydroxyhexyl sowie die Reste c!er I-'ormelnSmall radicals X and Y are, for example, the alkyl radicals methyl, ethyl, propyl, butyl, the hydroxyalkyl radicals / i-hydroxyethyl or -propyl. ; -Hyilroxypropyl. c-Hydroxyhexyl and the radicals c! er I-'formulas

--CH, -CH2-O CH2- CH2 OW --CH, -CH 2 -O CH 2 - CH 2 OW

-(CH2).,-O--(CH2U-OH- (CH 2 )., - O - (CH 2 U-OH

- (CH2)j - O (CH2),, OH- (CH 2 ) j - O (CH 2 ) ,, OH

CH (CH,), C OHCH (CH,), C OH

CH, CH,CH, CH,

CH., (H CJU
OHCH., (H CJU
OH

CH-CH2 (H2 -CH-CH 2 (H 2 -

-(UCH O- Cf,H,- (UCH O- C f , H,

CH, CW CJU CH, CW CJU

ICH2), O (CH2I2-O-CJlICH 2 ), O (CH 2 I 2 -O-CJl

-(CH2), O CH2 C11H5 - (CH 2 ), O CH 2 C 11 H 5

CW, O CH, CW, O CH,

CH, CW CH, CW

CH,CH,

OCOC

(CIM(CIM

O (CH-I, O CH.O (CH-I, O CH.

(CH2I, O (CH2I2 O KH2I2 O CH, (CH2I, O CHlCH-J2 (CH 2 I, O (CH 2 I 2 O KH 2 I 2 O CH, (CH 2 I, O CHlCH-J 2

und die '\cvloxvalkvlresie der Formelnand the '\ cvloxvalkvlresie of the formulas

(II, C\U (II, C \ U

O AcylO acyl

(CH2I, O Acyl CH, CH O Acvl(CH 2 I, O acyl CH, CH O Acvl

(H,(H,

O A cvlO A cvl

(CH2I2 - O (CI-M2 O Acyl (CH2),- O (CH2I4O Acyl -(H, CW C11H,(CH 2 I 2 - O (CI-M 2 O acyl (CH 2 ), - O (CH 2 I 4 O acyl - (H, CW C 11 H,

O AcylO acyl

COCH, Acylreste B MethylCOCH, acyl radicals B methyl

oder sind oderor are or

wobei Acyl beispielsweise —-COH.where acyl is for example -COH.

(O(U-O-C11H, sein kann, ferner COOB und CONHB, wobei Phenyl ist.(O (UOC 11 H, can also be COOB and CONHB, where is phenyl.

Zur Herstellung der Farbstoffe der Formel I kann man eine Diazoniumverbindung von Aminen der Formel 11To prepare the dyestuffs of the formula I, a diazonium compound of amines can be used Formula 11

Π Nil, (II)Π Nile, (II)

mit Kupplungskomponenten der Formel IIIwith coupling components of the formula III

XIINXIIN

NIIVNIIV

umsetzen, wobei I). R. X. Y in.<( / <lie π ilen Ansprüchen angegebene Bedeutung haben.implement, where I). R. X. Y in. <(/ <Lie π ilen claims have given meaning.

Die Dia/otienint' der Amine i-rlnli'l wir iihlirliThe dia / otienint 'of the amines i-rlnli'l we iihlirli

Die Kupplung wird ebenfalls wie üblich in wäßrigem Medium, gegebenenfalls unter Zusatz von Lösungsmitteln, bei schwach bis stark saurer Reaktion durchgeführt. The coupling is also as usual in aqueous Medium, optionally with the addition of solvents, carried out with weak to strongly acidic reaction.

Die Herstellung der Kupplungskomponenten der Formel III ist im Prinzip in der deutschen Patentschrift 20 62 717 beschrieben, die Angaben dort gelten hier sinngemäß.The preparation of the coupling components of the formula III is in principle in the German patent 20 62 717, the information there applies here analogously.

1 Mithalten die eriindungsgemäßen Farbstoffe der I onnel 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 lullen ist es aber auch zweckmäßig, den Saureres! (AcylI in den fertigen Farbstoff der Formel I einzuführen Da/u eignen sich die freien Säuren, ihre Anhydride. Chloride oder Fsler. wobei zweckmäßigerweise inerte Verdünnungs- oder Lösungsmittel, wie Mono-. Di- oder Trichlorbenzol. Tetrahydrofuran. Dioxan. Dimethylformamid. Nitrobenzol. N-Melhylpyrrolidon oder Pyridin zugesetzt werden.1 Keep up with the dyes according to the invention of the ion I an ester group in the radical X or Y. see above the compounds of the formula I can in principle be prepared by the specified process, if the corresponding ester group is already contained in the coupling component. In some But it is also useful to lull the sour food! (To introduce AcylI into the finished dye of the formula I. The free acids and their anhydrides are suitable for this. Chloride or Fsler. being expedient inert diluents or solvents, such as mono-. Di- or trichlorobenzene. Tetrahydrofuran. Dioxane. Dimethylformamide. Nitrobenzene. N-methylpyrrolidone or pyridine can be added.

Hei der Veresterung mit freien Säuren kann es von Vorteil sein, anorganische oder organische Katalysatoren, ζ. B. HO-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 Fisessig durchführen. Bei der Verwendung \on Säurechloriden als Verestcrungsmiltel ist es von Vorteil, dem Reaktionsgemisch säurebindende Mittel hinzuzusetzen, z. B. Natriumcarbonat oder -acetat. Magnesiumoxid oder Pyridin. Als Veresterungsmittel und Acylierungsmittel seien im einzelnen beispielsweise genannt: Ameisensäure, Essigsäure. Oiloressigsäurc, sowie die Ester, Anhydride oder Chloride dieser Säuren, weiterhin Chlorameisensäureäthylester oder Diketen sowie Isocyanate.In the case of esterification with free acids, it can be advantageous to use inorganic or organic catalysts, ζ. B. HO gas or p-toluenesulfonic acid. to add and to allow the water formed to escape from the reaction mixture by evaporation. If acid anhydrides or chlorides are used for esterification, then in In special cases, the relevant acids can also be used. So can the reaction with acetic anhydride perform in fisessig. When using acid chlorides as an esterification agent it is advantageous to add acid-binding agents to the reaction mixture, e.g. B. sodium carbonate or -acetate. Magnesium oxide or pyridine. As esterifying agents and acylating agents, there may be mentioned in detail named for example: formic acid, acetic acid. Oiloracetic acid, as well as the esters, anhydrides or Chlorides of these acids, also ethyl chloroformate or diketene and isocyanates.

Einzelheiten der Umsetzungen sind den Beispielen /u entnehmen.Details of the reactions can be found in the examples / u.

Technisch besonders wertvoll sind Farbstoffe und Farbsioffccmischc der Formel IaDyes and dye mixtures of the formula Ia are of particular technical value

A1 A2 A 1 A 2

R CNR CN

I = N--^. V-NH-Y1 (la)
NH-X1 I = N - ^. V-NH-Y 1 (la)
NH-X 1

in der A Nitro, Cyan, Chlor, Brom, Carbomethoxy. Carboäthoxy, /3-Methoxycarbäthoxy, Methylsulfonyl. Äthylsulfonyl, Methyl, Methoxy, Phenylsulfonyl, Phenylazo, A1 Wasserstoff, Nitro, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy, Carboäthoxy, Methylsulfonyl. A2 Wasserstoff, Chlor, Brom, Cyan. Methyl, Methoxy, Nitro, X1 und Y1 /S-Hydroxyäthyl. 7-Hydnsxypropyi oder einen F-est der Formeln ■in the A nitro, cyano, chlorine, bromine, carbomethoxy. Carboethoxy, / 3-methoxycarbethoxy, methylsulfonyl. Ethylsulfonyl, methyl, methoxy, phenylsulfonyl, phenylazo, A 1 hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl. A 2 hydrogen, chlorine, bromine, cyan. Methyl, methoxy, nitro, X 1 and Y 1 / S-hydroxyethyl. 7-Hydnsxypropyi or a solid of the formulas ■

— (CH2)2 — O — (CH2);, — OH- (CH 2 ) 2 - O - (CH 2 ) ;, - OH

— (CH2J3 — O — (CH2I4 - OH- (CH 2 J 3 - O - (CH 2 I 4 - OH

CII, CH C„ CII, CH C "

OH
CU2 CU2 C11H5 OH
CU 2 CU 2 C 11 H 5

(CH2),, OH(CH 2 ) ,, OH

- CH2 CH C6H5 ΠΙ.,- CH 2 CH C 6 H 5 ΠΙ.,

(CH2)., -O (CH2J2 - O- C6H5 (CH 2 )., -O (CH 2 J 2 -O- C 6 H 5

(CH2), Ο —CH2-C6H5 (CH 2 ), Ο -CH 2 -C 6 H 5

C6H5 C2H4-O-CH,C 6 H 5 C 2 H 4 -O-CH,

('.,H1, OCH, -CH2-CH2-OCHO('., H 1 , OCH, -CH 2 -CH 2 -OCHO

CH2 CH, CH2 Ο —CHOCH 2 CH, CH 2 Ο -CHO

CH2-CH2-OCOCH,CH 2 -CH 2 -OCOCH,

CH, CH2-O CH2-CH2-OCHOCH, CH 2 -O CH 2 -CH 2 -OCHO

CH, - CH2 -- OCOCH2 — O - C6H5 CH, - CH 2 - OCOCH 2 - O - C 6 H 5

und Wasserstoff, und R ein Alkylrest mit 2 bis 7 Kohlenstoffatomen oder Wasserstoff sind.and hydrogen, and R is an alkyl radical having 2 to 7 carbon atoms or hydrogen.

Besonders bevorzugt sind weiterhin Farbstoffe mit mindestens einem der genannten hydroxylgruppenhaltigcn Alkyl- oder Aralkylrcste.Dyes with are also particularly preferred at least one of the hydroxyl-containing alkyl or aralkyl radicals mentioned.

Besonders wertvoll sind auch die entsprechenden Farbstoffe, die als Diazokomponenten gegebenenfalls durch Nitro. Chlor. Brom. Cyan. Methyl. Meth\lmcrcapto. /i-Carbomethoxy-äthylmercapto. /i-Carb'omclhoxyäthoxy-äthylmereaplo. Carbomethoxy oder Acetyl substituiertes Benz.thiazol. Benzisothiazol. Thiazol. Thiadiaz.ol oder Thiophen enthalten.The corresponding dyes, which may be used as diazo components, are also particularly valuable through nitro. Chlorine. Bromine. Cyan. Methyl. Meth \ lmcrcapto. / i-carbomethoxy-ethyl mercapto. / i-Carb'omclhoxyäthoxyäthylmereaplo. Carbomethoxy or acetyl substituted benzothiazole. Benzisothiazole. Thiazole. Contain thiadiaz.ol or thiophene.

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-nilro-anilin.2-bromo-4-nilro-aniline.

2-Cyan-4-nitro-anilin.2-cyano-4-nitro-aniline.

2-Methoxy-4-nitro-anilin.2-methoxy-4-nitro-aniline.

2-Amino-5-nilro-phenylsulfonsäuredimelhvl-2-Amino-5-nilro-phenylsulfonsäuredimelhvl-

amid.amide.

2-Amino-5-nitro-phenylsulfonsäure-butylamid.
2-Amino-5-nitro-phenylsulfonsäure-/i-methoxy-2-Amino-5-nitro-phenylsulfonic acid-butylamide.
2-amino-5-nitro-phenylsulfonic acid / i-methoxy-

äthylamid,
2-Amino-benzonitril.
3-Chlor-4-amino-benzonitril.
2-Chlor-5-amino-benzonitril,
2-Amino-5-chlor-benzonitril.
3.5-Dich lor-2-amino-benzonitril.
1 -Amino^^dicyanbenzol,
l-Amino-2,4-dicyan-6-chlor-benzol,
2-Chlor-4-amino-5-nitro-benzonitril.ethylamide,
2-amino-benzonitrile.
3-chloro-4-aminobenzonitrile.
2-chloro-5-aminobenzonitrile,
2-amino-5-chloro-benzonitrile.
3.5-dichloro-2-aminobenzonitrile.
1-amino ^^ dicyanobenzene,
l-amino-2,4-dicyano-6-chlorobenzene,
2-chloro-4-amino-5-nitro-benzonitrile.

2-Amino-3-brom-5-nitro-ben£üniiril,2-Amino-3-bromo-5-nitro-ben £ üniiril,

2.6-Dicyan-4-nitro-anilin.2.6-dicyano-4-nitro-aniline.

2.5-Dichlor-4-nitroanilin.2.5-dichloro-4-nitroaniline.

2,6-Dichlor-4-nitro-anilin.2,6-dichloro-4-nitro-aniline.

Zo-Dibrom^-nitro-anilin.Zo-dibromo ^ -nitro-aniline.

2,4-Dinilro-anilin.2,4-dinilro-aniline.

2.4-I)initrii-6-eh!()r;milm.2.4-I) initrii-6-eh! () R; milm.

2.4-Dinitro-6-bri>m-anilin.2.4-dinitro-6-bri> m-aniline.

2-Amino-3.5-dinitro-benzonitril.2-amino-3,5-dinitro-benzonitrile.

I -Amino-4-nilrt>bcnzi»l-2-mcthylsiiHciti.I -Amino-4-nilrt> bcnzi »l-2-methylsiiHciti.

4-MclhylsLilfi)iiyl-anilin.4-MclhylsLilfi) iiyl-aniline.

l-AminoO-ehlorbenzoM-methylsulfon.l-AminoO-chlorobenzomethyl sulfone.

l-Amiiie>-2.fi-clibr()nibcn/ol-4-mclhylsiiHbii.l-Amiiie> -2.fi-clibr () nibcn / ol-4-mclhylsiiHbii.

l-Amino^/i-dichlorbenzol^-methylsulfon, 2- und 4-Amino-bcnzocsäurecslcr.l-amino ^ / i-dichlorobenzene ^ -methylsulfone, 2- and 4-amino-benzocic acid cslcr.

2-Λmino-5-nit ro-benzoesäureester.2-Λmino-5-nitro-benzoic acid ester.

2-Amino-3-chlor-5-niti"o-benzoesäureester.2-Amino-3-chloro-5-nitro-benzoic acid ester.

2-Λ mi η o-3.5-d ich lor-benzoesäureester.2-Λ mi η o-3.5-d i lorobenzoic acid ester.

2-Amino-3.5-dibrom-bcn/.oesäurcesicr.2-Amino-3,5-dibromo-bcn / .oic acid cicr.

2-Amino-3.5-dinitro-bcnzoesäure-mclhylesier2-Amino-3,5-dinitro-benzoic acid methylsier

oder -//-melhoxy-äthylester. 2-Amino-tercphlhalsäurc-diä thy !ester. 4-Amino-;i/o benzol.
2.3'-Dimelhvl-4-amino-a/o benzol. 2'.3-Di mctliyl-4-amino-azo benzol. 2.5-Dimcthyl-4-aniino-azoben/ol.or - // - melhoxy-ethyl ester. 2-Amino-terphlhalsäurec-diethyester. 4-amino-; i / o benzene.
2.3'-Dimelhvl-4-amino-a / o benzene. 2'.3-Dimethyl-4-amino-azo benzene. 2.5-Dimethyl-4-aniino-azoben / ol.

Von den besonders wertvollen heterocyclischen Diazokomponente!! seien erwähnt:Of the particularly valuable heterocyclic diazo components !! are mentioned:

2-Amino-5-nitro-lhiazol,2-amino-5-nitro-lhiazole,

2-Amino-4-mclhyl-5-nilro-thiazol, 2-Amiro-4-mcthyl-thiazol-5-carboiisäurcäthylester, 2-amino-4-methyl-5-nilro-thiazole, 2-Amiro-4-methyl-thiazole-5-carbonic acid ethyl ester,

2-Amino-5-pheny 1-1.3.4-1 hiadiazol. 3-Phcnyl-5-amino-I,2,4-thiadiazol, 3-Met hy l-mercapto-5-amino-l.2.4-1 hiadiazol. 3-/)-Carbomcthoxy-äthylmcrcapto-5-amino-2-amino-5-pheny 1-1.3.4-1 hiadiazole. 3-Phcnyl-5-amino-1, 2,4-thiadiazo l , 3-Met hy l-mercapto-5-amino-l.2.4-1 hiadiazole. 3 - /) - Carbomcthoxy-ethylmcrcapto-5-amino-

l.2.4-thiadiazol.
3-/<-Carboäthoxy-äthylmcrcapto-5-amino-1.2.4-thiadiazole.
3 - / <- Carboethoxy-ethylmcrcapto-5-amino-

1,2.4-thiadiazol,
2-A mino-6-c\;!n-benzlhiazol.
2-Λ min o-6-c:ir bon sau remct hy lcstcr-bcnzthiazol. 2-Amino-6-nitro-bcnzthiazol.
2-Amino-3-cyan-4-methyl-thiophen-5-carbonestcr, 1,2,4-thiadiazole,
2-A mino-6-c \ ;! n-benzlhiazole.
2-Λ min o-6-c: ir bon sau remct hy lcstcr-bcnzthiazol. 2-Amino-6-nitro-benzothiazole.
2-Amino-3-cyano-4-methyl-thiophene-5-carbon ester,

3-Amino-5-nitro-2,l-bcnzisothiazol. 3-Amino-5-nilro-7-chlor-2,l-benzisolhiazol. 3-Λ mino-5-n it ro-7-brom-2,1-benzisothiazol. 4-Amino-7-nit ro-1,2-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-Amino-5-nitro-2, l-benzisothiazole. 3-Amino-5-nilro-7-chloro-2,1-benzisole-thiazole. 3-Λ mino-5-n it ro-7-bromo-2,1-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 Textilmaterialien aus Acrylnitrilpolymensaten, synthetischen Polyamiden. Celluloseestern, wie 2''2- oder Triacetat, und insbesondere von synthetischen linearen Polyestern, wie PoIyäthylcnglykolterephthalat oder chemisch analog aufgebauten Polymeren.The new dyes are yellow to blue and are suitable for dyeing textile materials made from acrylonitrile polymers and synthetic polyamides. Celluloseestern such as 2 '' 2 - or triacetate, and in particular from synthetic linear polyesters, such PoIyäthylcnglykolterephthalat or chemically analog based polymers.

Die Farbstoffe können aus organischen Lösungsmitteln wie z. B. Perch loräthylen, nach dem Transfer-Verfahren und insbesondere auch aus wäßrigen Di spersionen 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. Perch loräthylen, after the transfer process and in particular from aqueous di spersionen and applied by the thermosol process. 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 in the examples relate to weight, unless otherwise stated.

Beispiel IExample I.

Lm Gemisch aus 1X7 Teilen 2.6-Dichloi-3-evan-4-älhy1p\ridin. 500 Teilen Methanol und 135 Teilen 2-Pheiiylpropylamin-f I) wird I Stunde bei ungefähr 25 bis maximal 55 C gerührt, dann set/i man 105 Feile Triäthylamiii innerhalb von 15 Minuten /ti und rührt weitere 6 Stunden bei ungefähr 45 bis 55 C. Dann destilliert man unter vermindertem Druck bei 50 bis 55 C etwa 250 Raumteile Methanol und überschüssiges Triäthylamiii ab, läßt etwas abkühlen und gibt den Rückstand unter Rühren in ein Gemisch aus etwa 1500 Teilen Wasser. 5(M) 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 C schmilzt.In a mixture of 1X7 parts of 2.6-dichloro-3-evan-4-alhy1pidine. 500 parts of methanol and 135 parts of 2-Pheiiylpropylamin-f I) is I hour at about Stirred at 25 to a maximum of 55 ° C., then set / i one 105 files of triethylamine within 15 minutes / ti and stir for a further 6 hours at approximately 45 to 55 ° C. Then, distillation is carried out under reduced pressure Pressure at 50 to 55 C about 250 parts by volume of methanol and excess Triäthylamiii, allowed to cool slightly and the residue is poured into a mixture of about 1500 parts of water with stirring. 5 (M) parts Ice and 50 parts of concentrated hydrochloric acid. The mixture is stirred for a further 1 hour, and the precipitate which has separated out is filtered off with suction off and dry. 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 /i'-Hydroxyäthylamin 4 bis 5 Stunden bei 130 bis 155 C gerührt. Dann läßt man erkalten und versetzt das Gemisch mit 200 Raumteilen Eisessig und 30 Raumtcilen konzentrierter Salzsäure. Man erhält eine Lösung der Kupplungskomponente der wahrscheinlichen Formel27.5 parts of this powder are mixed with about 60 parts / i'-hydroxyethylamine for 4 to 5 hours at 130 to 155 C stirred. The mixture is then allowed to cool and 200 parts by volume of glacial acetic acid are added 30 parts by volume of concentrated hydrochloric acid. A solution of the coupling component of the probable one is obtained formula

CH,CH,

NH-CH2-CH2-OHNH-CH 2 -CH 2 -OH

NH-CH2-CH-C6H5 NH-CH 2 -CH-C 6 H 5

die einen kleineren Anteil der Kupplungskomponente der wahrscheinlichen Formelwhich has a smaller proportion of the coupling component of the likely formula

C2H5 CNC 2 H 5 CN

NH-CH2-CH2 -OHNH-CH 2 -CH 2 -OH

NH-CH2-CH-C6H5
CH3 NH-CH 2 -CH-C 6 H 5
CH 3

enthält.contains.

Das Kupplungskomponentengemisch wird mit etwaThe coupling component mixture is with about

so 50 Teilen Eis versetzt und auf etwa 0'C abgekühlt.so added 50 parts of ice and cooled to about 0'C.

Dann gibt man in Anteilen gleichzeitig etwa 100 TeileThen about 100 parts are given in proportions at the same time Eis und eine Lösung von diazotiertem 2-Amino-Ice and a solution of diazotized 2-amino

5-nitrobenzonitriI zu, die wie folgt hergestellt wird:5-nitrobenzonitrile, which is produced as follows:

16,3 Teile 2-Amino-5-nitrobenzonitril werden unter16.3 parts of 2-amino-5-nitrobenzonitrile are under Rühren bei 0 bis 4r C so in ein Gemisch aus 50 Teilen konzentrierter Schwefelsäure und 13 Teilen 23%iger Nitrosylschwefelsäure 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.Stirring at 0 to 4 r C so in a mixture of 50 parts of concentrated sulfuric acid and 13 parts of 23% nitrosyl sulfuric acid added that the temperature does not at any time above 4 ° C. The mixture is stirred for 4 hours at 0 to 5 ° C. and then coupled as described above.

Zur raschen Beendigung der Kupplung, die bei etwa 0 C verlaufen soll, wird der pH des Gemisches durch Zugabe von Natriumacetat auf den Wert von 1,5 bis 23 eingestellt. Falls das Gemisch während der Kupplung schwer rührbar wird, kann man Eiswasser zu-To quickly end the coupling, which should take place at about 0 C, the pH of the mixture is increased Addition of sodium acetate adjusted to the value from 1.5 to 23. If the mixture becomes difficult to stir during the coupling, ice water can be added. setzen.set.

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 etwaThe mixture is stirred for a further 1 hour, then heated to 60 to 80 ° C. with steam, filtered off with suction, washes with water and dries. You get about

ι-ι-

47 Ί eile eines
liehen I-'ormeI47 Ί rush one
borrowed I-'ormeI

I'ulvers der wahiseliein-I'powder of the wahiseliein-

CN C,lls CNCN C, ll s CN

:> N N ·.■;:> N N ·. ■;

Ul,
Nil CII, (Il C„mUl,
Nile CII, (Il C "m

Nil CII, Cl-I, OHNile CII, Cl-I, OH

das einen kleineren Farbstoffanteil des 2.6-Alkylaniinopyridin-lsomeren enthält, sieh in Dimethylformamid mit roter Farbe löst und Polyäthylenterephlhalat-Ciewebe in kräftigen roten Tönen mit vorzüglichen Echtheiten färbt.that a smaller proportion of the dye of the 2,6-alkylaniinopyridine isomer contains, see dissolves in dimethylformamide with red color and Polyäthylenterephlhalat-Ciewebe dyes in strong red tones with excellent fastness properties.

H c i s ρ i e I 2 H cis ρ ie I 2

16.5 Teile der Diazokomponente der formel
CO(XH2CH2OCH,16.5 parts of the diazo component of the formula
CO (XH 2 CH 2 OCH,

O, NO, N

NII,NII,

werden mit ISO Raumlcilcn Eisessig, 18 Raiimtcilen konzentrierter Salzsäure und 20 Raumteilen Wassci versetzt. Man kühlt auf O bis 5 C ab, tropft 19 Raumteile 23%igc Nalriumnitrillösung zu und rührt 2
3 Stunden bei O bis 5"C. Dann verdünnt man die Diazoniumsalzlösung mit etwa 800 Teilen Eiswasser /erstört überschüssige salpetrige Säure wie iiblicr mil 19,5 Teilen einer Lösung oder Suspension dci und versetzt das Diazoniumsalzgcmisch in Anteilcr Kupplungskomponente der FormelISO volume glacial acetic acid, 18 volume parts concentrated hydrochloric acid and 20 volume parts water are added. The mixture is cooled to 0 to 5 ° C., 19 parts by volume of 23% strength sodium nitrile solution are added dropwise and the mixture is stirred for 2
3 hours at 0 to 5 ° C. The diazonium salt solution is then diluted with about 800 parts of ice water / destroys excess nitrous acid, such as usual, with 19.5 parts of a solution or suspension, and the diazonium salt mixture is added to the coupling component of the formula

C1H7(Ii) CNC 1 H 7 (Ii) CN

\v >- NH- CH2-CH2C6Hs
NM (H, CH,- OH\ v > - NH-CH 2 -CH 2 C 6 Hs
NM (H, CH, - OH

■u 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 Natronlauge zu, bis der pH-Wert des Gemisches■ u in a mixture of 150 parts of glacial acetic acid. 20 parts of concentrated hydrochloric acid and about 30 parts of water During the coupling, the mixture is cooled to 0 to 5 ° C. by adding a little ice and dilute sodium hydroxide solution is added until the pH value of the mixture is reached

^s etwa 2,5 beträgt. Nach beendeter Kupplung verdünnt man das Gemisch mit etwa 1000 Teilen Wasser, saugt den ausgefallenen Farbstoff der Formel^ s is about 2.5. Diluted after coupling is complete the mixture with about 1000 parts of water is sucked the precipitated dye of the formula

COOCH2-CH2-OCH, C,H7(n) CNCOOCH 2 -CH 2 -OCH, C, H 7 (n) CN

O2N-^O 2 N- ^

^ ν ■■---·—=--= N ^ ν ■■ --- · - = - = N

NHCH2-CH2-C6H5 NHCH 2 -CH 2 -C 6 H 5

NH-CH2 CH2-OHNH-CH 2 CH 2 -OH

ab, wäscht mil Wasser und trocknet. lenterephthalatgewebe nach Hochtemperatur-Färbe-off, wash with water and dry. lenterephthalate fabric after high-temperature dyeing

Man erhält ein dunkelr.ites Pulver, das sich in Di- verfahren in kräftigen roten Tönen mit sehr guten methylformamid mit roter Farbe löst und Polyäthy- 4° Echtheiten Färbt.A dark-white powder is obtained which, in the process, turns out to be strong red tones with very good ones methylformamide with red color dissolves and polyethy- 4 ° fastness dyes.

Beispiel 3Example 3

22 Teile 2.6-Dichlor-3-cyan-4-(n)-propylpyridin werden mit 100 Teilen Methanol gelöst, dann gibt man bei 45 bis 55"C 15 Teile des Amins der Formel22 parts of 2,6-dichloro-3-cyano-4- (n) -propylpyridine are dissolved with 100 parts of methanol, then there are one at 45 to 55 "C 15 parts of the amine of the formula

H2N-(CH2)3 —O(CH2)4OH H 2 N - (CH 2 ) 3 - O (CH 2 ) 4 OH

zu, rührt 30 Minuten, versetzt mit 20 Teilen Triäthylamin und rührt weitere 5 Stunden bei 45 bis 55 C. Dann destilliert man nach Zugabe von 30 Teilen )'-Hydroxypropylamin Methanol und Triäthylamin ab und rührt den Rückstand 4 Stunden bei 130 bis 145°C. Nach dem Erkalten wird das Reaktionsgemisch mit 60 Raumteilen Dimethylformamid versetzt und unter Rühren zu folgender Diazoniumsalzlösung gegeben:added, stirred for 30 minutes, mixed with 20 parts of triethylamine and stirred for a further 5 hours at 45 to 55 ° C. Then, after adding 30 parts of) '- hydroxypropylamine, methanol and triethylamine were distilled off and the residue was stirred at 130 to 145 ° C. for 4 hours . After cooling, the reaction mixture is mixed with 60 parts by volume of dimethylformamide and added to the following diazonium salt solution with stirring:

13.8 Teile p-Nitroanilin werden mit 100 Raumteilen Wasser und 30 Raumteilen konzentrierter Salzsäure 1 Stundegerührt, dann gibt man etwa 160Raumteile Wasser zu, kühlt auf 0° C ab, versetzt mit 33 Raumteilen 23%iger Natriumnitritlösung, rührt 2 Stunden, filtriert und zerstört einen etwa vorhandenen Überschuß an salpetriger Säure wie üblich. 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 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 one is destroyed any excess of nitrous acid present 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, wascht mit Wasser und trocknet.The coupling mixture is allowed to stir acidic for 1 hour, then aqueous sodium hydroxide solution is added until the pH of the mixture is about 2, sucks off the precipitated dye, washed 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

GH7(D) CN GH 7 (D) CN

O2NO 2 N

GH7(D) C> GH 7 (D) C>

N = N—<^>-NH—CH2-CH2-CH2-O-CH2-CH2-CH1-CH2-Oh NH- CH2 — CH2 — CH2 — OHN = N - <^> - NH-CH 2 -CH 2 -CH 2 -O-CH 2 -CH 2 -CH 1 -CH 2 -OH NH CH 2 - CH 2 - CH 2 - OH

das einen kleineren Anteil des Farbstoffes der Formelthat a smaller proportion of the dye of the formula

C1H7(H) CNC 1 H 7 (H) CN

O, NO, N

N NN N

> N> N

NH CH: ( H2 CH2 OHNH CH : (H 2 CH 2 OH

Nil CH2 CH2 CIK O CH2 CH2 CH2 CH2 OHNil CH 2 CH 2 CIK O CH 2 CH 2 CH 2 CH 2 OH

enthält und Polyäthylentercphthalalgewebe in kräftigen orangefarbenen Tönen mit vorzüglichen Fchtheilen nach Iloehtemperatur-Färbcverfahren färbt. Farbe der Lösung in Dimethylformamid: rotstichiges Orange.Contains and polyethylene terephthalal fabric in strong orange tones with excellent parts dyes by the low temperature dyeing process. Color of the solution in dimethylformamide: reddish orange.

e i spiel 4e i game 4

IO Teile des Farbstoffes der FormelIO parts of the dye of the formula

CN C1Ht(H) CNCN C 1 Ht (H) CN

Cl <^ J> N N-\ ;> NH CH2-CH1 CIK OH
Cl NH-CH2 CH2 CH, OHCl <^ J> N N- \;> NH CH 2 -CH 1 CIK OH
Cl NH-CH 2 CH 2 CH, OH

werden mit 80 Raumteilen Ameisensäure 10 Stunden unter Rückflußkühlung gerührt, dann destilliert man etwa 30 Raumteile Ameisensäure ab, versetzt den Rückstand mit etwa 150 Teilen Wasser, läßt erkalten, saugt den Farbstoff der Formelare stirred with 80 parts by volume of formic acid under reflux for 10 hours, then distilled for about 30 parts by volume of formic acid from, the residue is mixed with about 150 parts of water, allowed to cool, sucks the Dye of the formula

CNCN

C,H7(n) CNC, H 7 (n) CN

ClCl

·- ν ν --<■;· - ν ν - <■;

'.·>- NH -CH2 CH, CH2 OCHO'. ·> - NH -CH 2 CH, CH 2 OCHO

ClCl

NH CH2 CH2-CH2 OCHONH CH 2 CH 2 -CH 2 OCHO

ab. wäscht mit Wasser und trocknet. Man erhält em scharlachrotes Pulver, das sich in Dimethylformamid orangefarben löst und Polyäthylcntcrcphthalatgewcbe 40 C1H5 in orangefarbenen Tönen mit sehr guten Echtheiten färbt.away. washes with water and dries. A scarlet powder is obtained which dissolves in orange-colored dimethylformamide and dyes 40 C 1 H 5 polyethylcntcrcphthalate fabric in orange shades with very good fastness properties.

24 Teilen der Kupplungskomponente der Formel24 parts of the coupling component of the formula

CNCN

NII1 NII 1

;- ν; - ν

NH-CH2-CH1 C)-CO-CHNH-CH 2 -CH 1 C) -CO-CH

'2 O -C ,,H5 '2 O -C ,, H 5

in einem Gemisch aus etwa 500 Teilen Wasser und 20 Teilen Salzsäure laufen. Man rührt die saure Mischung etwa 15 Minuten und gibt dann innerhalb von etwa 30 Minuten wäßrige Natronlauge zu, bis 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 acid is stirred Mix for about 15 minutes and then add aqueous sodium hydroxide solution within about 30 minutes, until the pH of the coupling mixture is about 3. After stirring overnight, the dye becomes the formula

Beispiel 5Example 5

11.8 Teile 2-Aminobcnzonitril werden in 300 Raumteilen Wasser und 40 Raumteilen konzentrierter Salzsäure gelöst. Dann gibt man 300 Teile Eis und 33 Raumteile 23%ige Natriumnitritlösung 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 Diazoniumsalzlösung unter Rühren zu einer auf 5"C abgekühlten Lösung oder Suspension von11.8 parts of 2-aminobenzonitrile are dissolved in 300 parts by volume of water and 40 parts by volume of concentrated hydrochloric acid. 300 parts of ice and 33 parts by volume of 23% strength sodium nitrite solution are then added, the mixture is stirred for 2 hours at 0 to 5 ° C. and filtered. Any excess of nitrous acid that may be present is destroyed as usual, then the diazonium salt solution is left with stirring to form a solution or suspension of which has been cooled to 5 ° C

CN C2H, CNCN C 2 H, CN

<5-N-N-p<5-N-N-p

NH-CH2-CH2 C)-COCH2-O-QH5 NH-CH 2 -CH 2 C) -COCH 2 -O-QH 5

ibfiitriert. mit Wasser gewaschen und getrocknet. benen Arbeitsweisen werden die in den folgendenibfiitriert. washed with water and dried. Working methods are described in the following

vfan erhält ein gelbes Pulver, das sich in Dimethyl- Tabellen beschriebenen Farbstoffe hergestellt,vfan receives a yellow powder, which is produced in dyes described in dimethyl tables,

ormamid mit gelber Farbe löst und Polyäthylen- fts Die Farbtonangabe in den Tabellenbeispielen be-ormamid with yellow color dissolves and polyethylene fts.

erephthalatgewebe in kräftigen gelben Tönen mit zieht sich auf Färbungen auf Polyäthylenterephthalat-erephthalate fabric in strong yellow tones with pulls on dyeings on polyethylene terephthalate

orzüglichen Echtheiten färbt. gewebe. Analog zu den in den Beispielen 1 bis 5 beschrie-dyes excellent fastness properties. tissue. Analogous to those described in Examples 1 to 5

Tabelle 1Table 1

CNCN

CNCN

N-- N— ^N-- N- ^

}- N
NH X } - N
NH X

NH -- YNH - Y

Farbtonhue

--

— H- H

CH,CH,

CH,CH,

-C3H-InI-C 3 H-InI

KlKl C1H-HiIC 1 H-HiI IlIl C1H-InIC 1 H-InI ι;ι; CjHjCjHj C2H,C 2 H, 1414th C2H,C 2 H, 1515th CH,CH, HiHi C2H,C 2 H, 1717th -C1H-In)-C 1 H-In) ISIS HH WW. 1111th

CH, - CH,-OHCH, - CH, -OH

CU. CH, -CH, — OH CU. CH, -CH, - OH

CH, -CH, -CH,- OHCH, -CH, -CH, - OH

CH, - CH, - OHCH, - CH, - OH

CH, -CU, OHCH, -CU, OH

CH2-CH, OHCH 2 -CH, OH

CH2-CH2 — OHCH 2 -CH 2 - OH

CH2 -- CH, CH, OHCH 2 - CH, CH, OH

(CH2I1 -O (CH2), ·-() C„H,(CH 2 I 1 -O (CH 2 ), · - () C "H,

(CH2I1 - O - ICH2I, -■ O —C11H5 (CH 2 I 1 - O - ICH 2 I, - ■ O - C 11 H 5

(CH2I1 O (CH2I2 O- C11H5 (CH 2 I 1 O (CH 2 I 2 O- C 11 H 5

CH2 - CH, OHCH 2 - CH, OH

CH2 CH2 OHCH 2 CH 2 OH

— CH, — CH — C11H5 Scharlach- CH, - CH - C 11 H 5 scarlet

OH
CH2-CH-C11H5 ιοίOH
CH 2 -CH-C 11 H 5 ιοί

OH
-CH, -CH C,H, ιοιOH
-CH, -CH C, H, ιοι

OHOH

— CH, — CH- C,.H, rot- CH, - CH- C, .H, red

cncn

-CH2-CH-CH, rol-CH 2 -CH-CH, rol

OH
- CH2 - CH C11H5 ScharlachOH
- CH 2 - CH C 11 H 5 scarlet

OHOH

— CH, — CH2 — C11H, rol- CH, - CH 2 - C 11 H, rol

— C11H, hlausljchi- C 11 H, hlausljchi

— (CH,], — O — (CH2I, — O — CJU rol -ICH2I1-O- ICH2I2-O-C1H, - rot -ICH2I2-OH rot -(CH2I2-OH rol -(CH2I2-OH roi -CH2-CH-C11H, rol- (CH,], - O - (CH 2 I, - O - CJU rol -ICH 2 I 1 -O- ICH 2 I 2 -OC 1 H, - red -ICH 2 I 2 -OH red - (CH 2 I 2 -OH rol - (CH 2 I 2 -OH roi -CH 2 -CH-C 11 H, rol

CH,
CH2 -- CH -C11H5 rolCH,
CH 2 - CH -C 11 H 5 rol

OHOH

2121 IlIl (C(C. HH , (H,, (H, C]{, C! C] {, C! II,II, OllOll (H,(H, CH -CH - CJl1InICJl 1 InI C„H,C "H, CU, CU, OH CU, CU, OH rolrol c„Hsc "Hs OHOH -11-11 C1H-(IiIC 1 H- (IiI (H(H ,, CU, CCU, C H2 CHH 2 CH , CH,, CH, roiroi 2121 C1H-(IiIC 1 H- (IiI CC. (CH2Ia(CH 2 Ia OHOH UU ScharlachScarlet fever ICH2I4 I 2 I 4 OHOH 2424 C., H-In IC., H-In I. (C(C. Ή,Ή, ICIl2I4 ICIl 2 I 4 OHOH HH onon scharlaclsharp 2525th CJUCJU (C(C. IiIi ICH2I4 I 2 I 4 OHOH IlIl OHOH scharlaclsharp ->/-> / C2H,C 2 H, (C(C. HH CU,CU, CH2 CH 2 (II,(II, OHOH rolrol 2727 C1H-HiIC 1 H-HiI (C(C. HH CH2 CH 2 a':a ': CH2 CH 2 onon rolrol 2S2S C1H-In)C 1 H-In) HH (CH2I4 (CH 2 I 4 OCMOCM IOIO 1(11,11 (11.1 ., ο., ο (CIl, I1,(CIl, I 1 , OCIK)OCIK) scharlaclsharp 2929 C , 11,C, 11, HH O (O ( II; CII; C. II,II, OHOH (CH.i(CH.i OO ICH-I4 I-I 4 H1 H 1 scharlaclsharp 1(11 (1 CjIl,CjIl, (C(C. ΊΙΊΙ O (O ( 11, C11, c H2 H 2 OllOll cn.cn. (II.(II. Ή,Ή, scharlaclsharp IiIi CH,CH, CC. •I;• I; O (O ( II. CII. C I 1 .I 1. OHOH CH,CH, cn.cn. O (O ( H1 H 1 lotlot 1212th CJUCJU CC. II,II, O (O ( II. CII. C U,U, OllOll cn.·cn. cn.cn. O (O ( OCH,OCH, roiroi 1.11.1 C1II-C 1 II- CC. II,II, O (O ( II, C II, C Ί;Ί; OHOH cn.cn. CIl.CIl. O (O ( ΙΟΙΙΟΙ .14.14 C1II-C 1 II- CC. H;H; O (O ( II, CII, C II,II, OHOH CU,CU, cn.,cn., CII,CII, rolrol J<J < C1II-C 1 II- CC. II;II; I ) (I) ( II. CII. C H.H. OHOH IlIl rolrol M>M> C1II-C 1 II- CC. II,II, cn.cn. ΙΟΙΙΟΙ 1717th CIICII (( II.II. lotlot ,I1 OH, I 1 OH CU2 (H CU 2 (H -CII-CII OHOH ,1, O, 1, O ..κ ο..κ ο ..).. ο..) .. ο .,I1 O., I 1 O ,1, O, 1, O ClI,ClI, (II,(II, cn.cn. CH.CH. (II.(II. (II.(II. (Il(Il

1717th

CN R CNCN R CN

Tabelle 2Table 2

Ο,Ν—<f "*>—N = N-<. >—NH-YΟ, Ν— <f "*> - N = N- <.> —NH-Y

Cl HN-XCl HN-X

Nr. R XNo. R X

ft*ft *

1818th

FarbionColor ion

38 —Η38 -

39 -C2H5 39 -C 2 H 5

-CH2-CH2-OH-CH 2 -CH 2 -OH

-CH2-CH-C11H5 -CH 2 -CH-C 11 H 5

rubinruby

-QH--QH-

-QH- -Q H, -QH7 -C3H, -C1H, C, H7 -QH,-QH- -QH, -QH 7 -C 3 H, -C 1 H, C, H 7 -QH,

-C, H,-C, H,

50 - C1H-50 - C 1 H-

51 C3H,51 C 3 H,

QH, C1H7 QH7 Q H-(Ii)QH, C 1 H 7 QH 7 Q H- (Ii)

Tabelle 3Table 3

C"NC "N

HrMr

-OH-OH OHOH -H-H rubinruby CH2-CH2-OHCH 2 -CH 2 -OH -OH-OH -CH2-CH-C11H5 -CH 2 -CH-C 11 H 5 -H-H -OH-OH OHOH rubinruby CH2-CH2-OHCH 2 -CH 2 -OH -CH2-CH-CnH5 -CH 2 -CH-C n H 5 — Η- Η i
OHi
OH rubinruby CH2-CH2-OHCH 2 -CH 2 -OH -(CH2I3-O-(CH2U-OH- (CH 2 I 3 -O- (CH 2 U-OH — Η- Η rubinruby CH2-CH2-OHCH 2 -CH 2 -OH -(CH2),-0-(CH2I2-0-C11H5 - (CH 2 ), - 0- (CH 2 I 2 -0-C 11 H 5 MM. rubinruby CH2-CH2-OHCH 2 -CH 2 -OH — (CH2), — O — CH2 — CnH5 - (CH 2 ), - O - CH 2 - C n H 5 -CH2-CH2-O-CH,-CH 2 -CH 2 -O-CH, rubinruby CH2-CH2-O-CH2-CH2-CH 2 -CH 2 -O-CH 2 -CH 2 - -CH2-CH2-O-CH,-CH 2 -CH 2 -O-CH, rubinruby CH2-CH2- O- CH2- CH2-CH 2 -CH 2 - O- CH 2 - CH 2 - -QH5 -QH 5 rubinruby CH2 — CH2 — O — CH2 — CH2 -CH 2 - CH 2 - O - CH 2 - CH 2 - — C3H7(n|- C 3 H 7 (n | blaustichigrobluish green HH -QH5 -QH 5 blaustichigrobluish green HH -Q, H5 -Q, H 5 — (CH2I3 — O — ICH2I4 — OH- (CH 2 I 3 - O - I CH 2 I 4 - OH blaustichigrobluish green HH -CH2-CH-CnH5 -CH 2 -CH-C n H 5 CH2 CH1-O-CH2-CH2-OCHOCH 2 CH 1 -O-CH 2 -CH 2 -OCHO OHOH blausHchigroblue chigro (CH,)3 — O — (CH2)4 — OH(CH,) 3 - O - (CH 2 ) 4 - OH blaustichigrobluish green CH2-CH-QH5 CH 2 -CH-QH 5 OHOH blauslichigrobluishro CH2-CH2-OHCH 2 -CH 2 -OH blaustichigrobluish green CH2-CH2-CH2-OHCH 2 -CH 2 -CH 2 -OH blaustichigrobluish green CH2 — CH2 — O — COCH2 - OCH 2 - CH 2 - O - COCH 2 - O blaustichigrobluish green (CH2), -O—(CH2)4 — OH(CH 2 ), -O- (CH 2 ) 4 - OH blaustichigrobluish green

R CNR CN

l-< >-NH-~Yl- <> -NH- ~ Y

/N/ N

HN —XHN -X

Farbtonhue

5757 -Il-Il ' Is'Is CC. 1II2 1 II 2 CC. ' I2'I2 - OH- OH CH,CH, CII2 CII 2 OHOH CH2 CH 2 -CH
ι-CH
ι In)In) -QH5 -QH 5 onon rubinruby CH,CH, CHjCHj OilOil OHOH O C11H5 OC 11 H 5 5X5X C2 C 2 II-II- CC. H2 -H 2 - CC. H2 H 2 — Oll- Oll CH,CH, CW,CW, OHOH CH2 CH 2 -CH-CH -Q1Hs-Q 1 Hs ,Hs, Hs rubinruby OHOH 5')5 ') QQ W-W- (( •H;•H; (( ΊΙ,ΊΙ, OilOil -CH2 -CH 2 CHCH - QIK- QIK rubinruby IlIl OHOH i>0i> 0 C1 C 1 II,II, (( H2 H 2 CC. "H2 "H 2 OHOH KII,KII, Ii OIi O ICH2I4 I 2 I 4 rubinruby (.1(.1 C1 C 1 II.II. (( -H2 -H 2 (( 'H2 'H 2 OHOH (CH2 (CH 2 Ii OIi O (CH2),(CH 2 ), rubinruby ί..1 ί .. 1 C,C, II.II. (( H,H, (( 'H2 'H 2 OHOH (CH2 (CH 2 l.i Ol.i O CH2 C,CH 2 C, rubinruby ()3() 3 C,C, IlIl (( II,II, (( HjHj OO C HjC Hj CH,CH, 0 cn0 cn rubinruby MM. C1 C 1 (( HjHj (( ΊΙ,ΊΙ, OO CjIUCjIU rubinruby (ό(ό C1 C 1 (( ΊΙ,ΊΙ, (( ΊΙ,ΊΙ, OO C1II,C 1 II, rubinruby

19 * w 2019 * w 20

Nr. RX Y FarbionNo. RX Y color ion

6666 - C1H,- C 1 H, 44th NO,NO, -H-H -(CH2I4- OH- (CH 2 I 4 - OH -C11H5 -C 11 H 5 I1-O-(CH2I4-I 1 -O- (CH 2 I 4 - OHOH blausiichigrobluishigro 6767 - CyH- - CyH- -N =-N = — H- H -C11H5 -C 11 H 5 (CH2 (CH 2 blausliehigroblue, green 6X6X - CH-- CH- - H- H - CH2 - CH 2 OHOH blausiichigrobluishigro — OH- OH 6464 -C1H--C 1 H- -(CH2I1-O- (CH 2 I 1 -O - CH2 — OH- CH 2 - OH -H-H blausiichigrobluishigro 7070 - C1H,- C 1 H, — CH, — CH -- CH, - CH - O -CO(II2-O-C1H,O -CO (II 2 -OC 1 H, — H- H blausiichigrobluishigro OHOH ICII2I4 OHICII 2 I 4 OH 7171 - CH,- CH, -CH2-CH2 -CH 2 -CH 2 — H- H blaustichigrobluish green 7:7: -C1H,-C 1 H, -CH2-CH2 -CH 2 -CH 2 IIII blaust ich igroI blush igro 7,7, — CH-- CH- —CH,-CH,-CH, -CH, -H-H blausiichigrobluishigro 7474 -Il-Il ICH2I1 OI 2 I 1 O HH blaustichigrobluish green 7575 C1H-(Ii)C 1 H- (Ii) -C2H,-C 2 H, - C2H5 - C 2 H 5 hiaustithiurohiaustithiuro TabelleTabel R CNR CN O,N -O, N - N^f~ '/-NH -YN ^ f ~ '/ -NH -Y >N> N NH-XNH-X

Nr. RX Y FarbtonNo. RX Y shade

76 -H —Η -(CH2I1-O-(CH2I4-OH rot76 -H -Η - (CH 2 I 1 -O- (CH 2 I 4 -OH red

77 -C2H5 -H - (CH2), — Ο— (CH2I4- OH rot 7S -C1H7 —H -(CH2Ij-O-(CH2I4-OII ml 74 "C11H, -H ICH2I1 -O — (CH,)4 -OH ml77 -C 2 H 5 -H - (CH 2 ), - Ο- (CH 2 I 4 - OH red 7S -C 1 H 7 -H - (CH 2 Ij-O- (CH 2 I 4 -OII ml 74 "C 11 H, -H I CH 2 I 1 -O - (CH,) 4 -OH ml

SO CH-C4H, -CH1-CH, OH — CH, — CH,- OH dunkelrolSO CH-C 4 H, -CH 1 -CH, OH - CH, - CH, - OH dark red

C2H5 C 2 H 5

Xi C1H, —Η CH,-CH-Q1H5 rutXi C 1 H, -Η CH, -CH-Q 1 H 5 rut

OHOH

Χ: C1H7 -CH2 CH C11H5 -H rotΧ: C 1 H 7 -CH 2 CH C 11 H 5 -H red

OHOH

X.I C1H- -(CH2I1-O-(CH2I4-OH - H rotXI C 1 H- - (CH 2 I 1 -O- (CH 2 I 4 -OH - H red

X4 -C1H7 -CH2-CH2-O-CH2-CH2-OIl - CH2-CH2--O-CH, dunkclrotX4 -C 1 H 7 -CH 2 -CH 2 -O-CH 2 -CH 2 -OIl - CH 2 -CH 2 --O-CH, dark red

X5 -C1H, -CH2-CH,— O-CH2 CH2 Oil --CH2 — CH2-CH2-■ O-CH, dunkclrotX5 -C 1 H, -CH 2 -CH, - O-CH 2 CH 2 Oil --CH 2 - CH 2 -CH 2 - ■ O-CH, dark red

X6 - C1I-I7 -CH2-CH2-OH - C11H5 blaustichigr«X6 - C 1 II 7 -CH 2 -CH 2 -OH - C 11 H 5 bluish tint "

X7 C1H, CH2-CH2-OH — CH2 -CH2 C11H5 dunkelrolX7 C 1 H, CH 2 -CH 2 -OH - CH 2 -CH 2 C 11 H 5 dark red

XX -C1H-, CH2-CH1 OH -CH2-CH-C11II5 dunkelrotXX -C 1 H-, CH 2 -CH 1 OH -CH 2 -CH-C 11 II 5 dark red

OHOH

X') C2H5 CIl, CII2 Oll CH2 CH-C11H5 dunkclrotX ') C 2 H 5 CIl, CII 2 Oll CH 2 CH-C 11 H 5 dark-red

OHOH

40 C1H- CH2-CH2-OH CH,- CH-C11H5 dunkelrol40 C 1 H- CH 2 -CH 2 -OH CH, - CH-C 11 H 5 dark red

CU.,CU.,

1JI C1Il- CW2 CII2 OH CII2-- CH C11H, dunkelrol 1 JI C 1 II- CW 2 CII 2 OH CII 2 - CH C 11 H, dark red

OHOH

4.: C1II- CH2 CII, CH, OH CII, CIl CII, dunkelrol4 .: C 1 II- CH 2 CII, CH, OH CII, CIl CII, dark red

OHOH

Ή C1H. CW, CW. (KH1CH1OCHO CII. CII, O CIl, dunkeln,'.Ή C 1 H. CW, CW. (KH 1 CH 1 OCHO CII. CII, O CIl, dark, '.

1M C1IlIIi) (CH2I1 0 KU, I4 Oll CH, CH2 CII, -Oll dunkelrol 1 MC 1 IlIIi) (CH 2 I 1 0 KU, I 4 Oll CH, CH 2 CII, -Oll dark red

1JS C1IIIn) CII, ClI. OH ICIl2I1 O ((H2I, O C11Il, dunkelrol 1 JS C 1 IIIn) CII, ClI. OH ICIl 2 I 1 O ((H 2 I, OC 11 II, dark red

')(, (Ml.nil CMl. CMI, diinkelrot') (, (Ml.nil CMl. CMI, diinkelrot

Tabelle 5Table 5

2121

Nr. RNo. R

CM R CNCM R CN

Ο,Ν — ? --N N -<f : ~ NH --YΟ, Ν -? --NN - <f : ~ NH --Y

NH ■■ YNH ■■ Y

2222nd

l'arbh'iil'arbh'ii

4747 - H- H -■ H- ■ H O -O - -IC)I-IC) I 4S4S C2H5 C 2 H 5 HH οο ICHI 4949 -- C1H-(IiI- C 1 H- (IiI - Il- Il CHCH C ILC IL 100100 -C5HnOiI-C 5 H n OiI — H- H 101101 — C11H5 - C 11 H 5 — Η- Η arar - C2H,- C 2 H, -(CH2I1 - (CH 2 I 1 |Πλ| Πλ C1H-(IiIC 1 H- (IiI (CMLl1 (CMLl 1 104104 CH-! IllCH-! Ill (H,(H,

C1H onC 1 H on

C1H-IiIiC 1 H-IiIi

— Ο||- Ο ||

OHOH

CIL OHCIL OH

(C(C. Π,ι,Π, ι, OO (C(C. II,II, I4OIII 4 OII ICIC H2UH 2 U OO (C(C. MiWed IjOHIjOH (C(C. H2I1 H 2 I 1 {ι{ι KK ll,ll, I4OIII 4 OII ICIC H2UH 2 U OO IlIl II,II, I4OHI 4 OH (C(C. H2I,H 2 I, OO KK H:H: ι.οηι.οη HH

(Mi. cn c π.(Mi. cn c π.

OH
CIIOH
CII

CJLCJL

scharlach scharlach scharlach scharlach scharlach scharlach scharlach schal lachscarlet scarlet scarlet scarlet scarlet scarlet scarlet shawl laugh

schail.ich schal I.ichschail.ich scarf I.i

C1H-OiIC 1 H-OiI

CiL cn, cCiL cn, c

(H C1JI.(HC 1 JI.

CC. Ml-Oi]Ml-Oi] CC. II,II, (.(. H,H, CILCIL OllOll ICIC ILuILu OHOH (CII2I.. O(CII 2 I .. O IUSIUS CC. '.,H-(IiI'., H- (IiI CC. ILIL (( 'H2 'H 2 OHOH icic MLl1 MLl 1 OO (C Ί l,i. O(C Ί l, i. O ΙΟΊΙΟΊ (( -,Η-(η)-, Η- (η) ICIC "H2I.,"H 2 I., OO ICH,I, ι, Ο (JLι, Ο (JL CC. ILIL OO I 1III 1 II I IOI IO CC. ",!■!-(πι",! ■! - (πι icic MLl,MLl, OO (CII,(CII, I, OllI, Oll CC. 11,11 (H.(H. CW, O CW, O IIIIII CC. -,H-OH-, H-OH (C(C. MLl1 MLl 1 OO (CH2 (CH 2 Ij OHIj OH CC. IlIl cn.cn. O CII1 O CII 1 I 12I 12 CC. ",H-InI", H-InI CC. ILIL (( MI2 WED 2 OHOH CC. H,H, (H,(H, C1Jl,C 1 Jl, I IoI Io CC. -,IU-, IU - C- C Ii,Ii, CC. H,H, OHOH CC. ILIL (H,(H, CJLCJL I 14I 14 (( ',H5 ', H 5 CC. II,II, CC. Ml,Ml, -O-O (-H2ClI2 Oll(-H 2 ClI 2 Oll CC. JLJL CII2 CII 2 115115 CC. ',H5 ', H 5 CC. H,H, CC. II,II, OHOH C1 C 1 JLJL I UiI Ui CC. ",H-(IiI", H- (IiI CC. MLML CC. MLML 117117

Tabelle 6Table 6

HrMr

CNCN

Ο,Ν ■'* 'V-N = N-V* :;/-Nll -YΟ, Ν ■ '*' UN = NV *:; / -Nll -Y

>N NH -X C1JU > N NH -X C 1 JU

cn,cn,

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

scharlachScarlet fever

ticlhsiichiüticlhsiichiü

L'clbslichi;:L'clbslichi ;:

scharlachScarlet fever

l-arhlonl-arhlon

MKMK HH H5 H 5 HH OO (CII., I4 (CII., I 4 OHOH 119119 C1 C 1 H7(MlH 7 (Ml HH OO (CII, I.,(CII, I., OllOll 120120 C1 C 1 H11OiIH 11 OiI HH CHCH C, IUC, IU 121121 C5 C 5 H5 H 5 IlIl 122122 - c„- c " HH 12.112.1 C1 C 1 Il-di)Il-di) (CII;).,(CII;)., 124124 C,C, H-(HlH- (St. (ClI,),(ClI,), 125125 C1 C 1 cn.cn.

onon

(CH2I1 O (CIl2I4OII(CH 2 I 1 O (CIl 2 I 4 OII

(CH2I1 0-((MLl4OH(CH 2 I 1 0 - ((MLl 4 OH

(CH,), O (CIL)4OlI(CH,), O (CIL) 4 OlI

(CIL)1 O (CILI4OII(CIL) 1 O (CILI 4 OII

K H2I, O (CIL)2OIIKH 2 I, O (CIL) 2 OII

(Ml-oii Cl(Ml-oii Cl

scharlach scharlach scharlach scharlach scharlach scharlach scharlach -cha ι lachscarlet scarlet scarlet scarlet scarlet scarlet scarlet -cha ι laugh

scharlachScarlet fever

ortscl/uiit-'ortscl / uiit- '

(',H.liil
C,M nil(', H.liil
C, M nil

C,ll.dil
(',ll-liilC, ll.dil
(', ll-liil

I1IIiMi
(',lldiiI 1 IIiMi
(', lldii

< ,11 mi<, 11 mi

< ,11 Hn
(Ml,<, 11 Hn
(Ml,

( .IK (Ml.(.IK (Ml.

1.1 hell,1.1 bright,

(II, CH. Oil(II, CH. Oil

(II, (II, (II, Oll(II, (II, (II, Oll

CII. CII, CH, OllCII. CII, CH, Oll

CH, CH, OllCH, CH, Oll

((11,I1 O ICH,)., O C„l\^ ((11, I 1 O I,)., O C "l \ ^

(CII, I, O ICH, I, OH(CII, I, O I, I, OH

ICH., ι., O ICHj4 Oll, Ι I.., 4 O ichj Oll

(II, (II. OH(II, (II. OH

CH, CII, OilCH, CII, Oil

CH, (II, O CH, CH, OllCH, (II, O CH, CH, Oll

(II, CH, OH(II, CH, OH

KK NN (N(N \\ NHNH NilNile

11 CH,CH, CWCW CJI,CJI, I'arblonI'arblon OilOil ScharlachScarlet fever CH,CH, CH
]CH
] CJl,CJl, OHOH ScharlachScarlet fever (CH2 (CH 2 I, OI, O (CW,)2 O (CW,) 2 O CJUCJU ScharlachScarlet fever (CH2 (CH 2 ι., οι., ο ICW2U O- ICW 2 U O- CH2 CH 2 CW2 CW 2 OHOH ScharlachScarlet fever CH,CH, CH2 CH 2 CH2 O CH1 CH 2 O CH 1 ScharlachScarlet fever ('H, ( 'H, (H,(H, O (H,O (H, ScharlachScarlet fever CH,CH, CW2 CW 2 CJI,CJI, ScharlachScarlet fever CH,CH, <ΊΙ,<ΊΙ, CJI,CJI, schallachschallach CJI,CJI, scharliichsharp QII,QII, gelbstichigyellowish gelbstichigyellowish

Kai btonKai bton

4141 ( ,11..(, 11 .. (CH,(CH, I, OI, O (CH2Ij ■■ C(CH 2 Ij ■■ C ■V■ V (Ml.(Ml. (H,(H, (H(H CJI,CJI, OHOH 4!4! ( .H.( .H. (H,(H, CH,CH, CH, - OHCH, - OH 4444 (', Il„(', Il " CH,CH, CH.CH. OHOH CH.CH. -CH,-CH, - CH.- CH. OHOH

— CH,- CH,

-C, H-I η ι-C, H-I η ι

4S4S — C,H-(nl- C, H- (nl 4949 — C, H-I η)- C, H-I η) 5050 — C,H-in)- C, H-in) 5151 CH,CH, -C2H,-C 2 H, -C3H,ln|-C 3 H, ln | >4> 4 — C3H,(n|- C 3 H, (n | 5555 — C3H7In)- C 3 H 7 In) S6S6 Ϊ7Ϊ7 — C,H,(nl- C, H, (nl

— CH, — CH2 — OH -CH, -CH, -OH- CH, - CH 2 - OH -CH, -CH, -OH

-CH,-CH2-OH-CH, -CH 2 -OH

— CH2 — CH, — OH- CH 2 - CH, - OH

-CH2-CH3-OH-CH 2 -CH 3 -OH

— CH, - CH2 — OH CH2 - CH, - CH 2 - OH CH 2

-CH2-CH, — O -CH, — CH, — OH-CH 2 -CH, -O -CH, -CH, -OH

— CH2 — CH2 — O — CH2 — CH, — OH- CH 2 - CH 2 - O - CH 2 - CH, - OH

— (CH21., - O - (CH2), - O — QH, -C2H5 - (CH 2 1., - O - (CH 2 ), - O - QH, -C 2 H 5

— H- H

(CH(CH ,!, O ,!, O (CH2I, OH(CH 2 I, OH orangeorange KHKH ,ι,- o, ι, - o -ICH2I4 OH-I 2 I 4 OH orangeorange CH2 CH 2 CHCH -QH,-QH, .-range.-range OllOll HH oiangelong HH orangeorange HH orangeorange HH orangeorange CH,CH, CH.CH. QH,QH, rotstichigesreddish Orangeorange CH7 CH 7 -CH-CH - QH5 - QH 5 rotstichigesreddish OHOH Orangeorange CH,CH, -CH-CH -QH,-QH, rotstichicesrotstichices OHOH Orangeorange (CH,(CH, ), — O ), - O -(CH2I2-O-QH,- (CH 2 I 2 -O-QH, rotstichiges
Oranucreddish
Oranuc CH,CH, -CH-CH -O-QH,-O-QH, rotstichigesreddish CH,CH, Orangeorange QH,QH, ScharlachScarlet fever QH,QH, ScharlachScarlet fever QH,QH, ScharlachScarlet fever CH,CH, -CH,-CH, — OCH,- OCH, orangeorange (CH2 (CH 2 1,-01, -0 -CH(CH, I,-CH (CH, I, orangeorange CH2 CH 2 -CH,-CH, -OH-OH orangeorange C2H.C 2 H. orangeorange HH gelbyellow

2525th

Γ(>ιΊΜ.Ί/ιιημΓ (> ιΊΜ.Ί / ιιημ RR. CIUCIU XX KK 11.111.1 ι Oι O NrNo C1M-HiIC 1 M-HiI CC. 11,11 CMCM ,SS, SS OMOM is·*is * CMUCMU CC. II,II, CMCM IN)IN)

CJUCJU

OilOil

CIl.. CII, CM, OM
(II., ClI, O CII, CCIl .. CII, CM, OM
(II., ClI, O CII, C

(M, O CH. C(M, O CH. C

I'iirblonI'iirblon

OlilM^C Oil OKIIIl-1I1 OlilM ^ C Oil OKIIIl- 1 I 1

OH oKinyeOH oKinye

IM CIU «'!!,I, O ICM, I, OCIIOIM CIU "'!!, I, O ICM, I, OCIIO

KO CIU ICH,I, O (CIUl,KO CIU I, I, O (CIUl,

COCIl",'COCIl ", '

KvI CIU (CHjI1 O IC Η,), Ο C,,IUKvI CIU (CHjI 1 O IC Η,), Ο C ,, IU

CHj -CH, (KII,
CMj C\l: OCM,CHj -CH, (KII,
CMj C \ l : OCM,

CM, CM, OCH1 CM, CM, OCH 1

ItIiUl 120ItIiUl 120

orangeorange

Tabelle STable p

H1COjS O, N ■H 1 COjS O, N ■

R CNR CN

NN- Nil VNN- Nile V

NH XNH X

Farbtonhue

CICI

C1H-In)C 1 H-In)

CjH, CjH5 C1H7In) C1H7In)CjH, CjH 5 C 1 H 7 In) C 1 H 7 In)

-C3H7(n) CjH,-C 3 H 7 (n) CjH,

QH11In) - C3H7(n)QH 11 In) - C 3 H 7 (n)

180 — QH7(n)180 - QH 7 (n)

!8I! 8I — C3H7(H;- C 3 H 7 (H; 182182 -C2H,-C 2 H, 183183 - C3H7(n)- C 3 H 7 (n) 184184 -C3H7(P)-C 3 H 7 (P) 185185 -- C3H,(n)- C 3 H, (n) 186186 - C3H,(n)- C 3 H, (n)

Il H HIl H H

itiXitiX 11 ',M-(IiI', M- (IiI ICHjI y I, - oI, - o (CHjI4-(CHjI 4 - OHOH IWIW CC. ',H7In)', H 7 In) (CH2 (CH 2 )., — O)., - O -ICHj)4 --ICHj) 4 - OHOH 170170 CC. ',H,In)',There) CH2 CH 2 — C H;- C H; - OH- OH 171171 CC. ",Η,(η)", Η, (η) CH,CH, -CH,-CH, — OH- OH

CH2 CH2 CH 2 CH 2

OHOH

CH2 - CH2 — OH CH2 -CH2 OH -TH1-CH1-CH1--OHCH 2 - CH 2 - OH CH 2 -CH 2 OH -TH 1 -CH 1 -CH 1 --OH

-CH2-CH2-OH-CH 2 -CH 2 -OH

- CH2 — CH2 — OH- CH 2 - CH 2 - OH

-CH2-CH2 — O — CHj -CH2 — OH-CH 2 -CH 2 - O - CHj -CH 2 - OH

- CH2 — CH2 — OH- CH 2 - CH 2 - OH

— CH2 — CH2 — OH- CH 2 - CH 2 - OH

— CH2 — CH2 — QH5 -CH2-CH2-QH5 -CH2-CH2-O- CO-CH2-O-QH5 - CH 2 - CH 2 - QH 5 -CH 2 -CH 2 -QH 5 -CH 2 -CH 2 -O- CO-CH 2 -O-QH 5

— CH2 — CH2 — CH2 - O — CHO- CH 2 - CH 2 - CH 2 - O - CHO

— (CH2Jj — O — (CHj)2 — OCHO- (CH 2 Jj - O - (CHj) 2 - OCHO

— (CH2)J - O - (CHj)2 - OCOCH3 - (CH 2 ) J - O - (CHj) 2 - OCOCH 3

(CH2).,(CH 2 )., — O- -(CIIj)4 -OH- O- - (CIIj) 4 -OH CH3 CH 3 rotRed (CHj),(CHj), — O--(CTI,),,- OH- O - (CTI,) ,, - OH (CHj)3 -C-OH
CH3 (CHj) 3 -C-OH
CH 3 rotRed CHjCHj CH — C11H5 CH - C 11 H 5 rotRed C)HC) H CH,-CH, - CH - C11H5 CH - C 11 H 5 rotRed OHOH HH -CHj — CH2 — OCHO-CHj - CH 2 - OCHO rotRed CH2 -CH 2 - CH, — CHj — OHCH, - CHj - OH - CH2 — CH2 — O — COCH3 - CH 2 - CH 2 - O - COCH 3 rubinrolrubinrol CH,-CH, - CH2-QH5 CH 2 -QH 5 rubinrotRuby red CH2-CH 2 - CH - QH5 CH - QH 5 rubinrotRuby red I
CH3 I.
CH 3 CH2-CH 2 - CH-QH5 CH-QH 5 rubinrotRuby red CH,CH, (CH2).,(CH 2 )., - (J-(CH2),-O-QH5 - (J- (CH 2 ), - O-QH 5 rubinrotRuby red (CH2I3 (CH 2 I 3 -O-(CH2)j—0-Q1H5 -O- (CH 2 ) j-O-Q 1 H 5 rubinrotRuby red CH2-CH 2 - CH - QH5 CH - QH 5 rubinrotRuby red I
OH I.
OH QH,QH, rubinrotRuby red QH,QH, rubinrotRuby red CH2-CH 2 - CHj-O-CH3 CHj-O-CH 3 rubinrotRuby red CH2-CH 2 - CH2-CH-QH5 CH 2 -CH-QH 5 rubinrotRuby red CH3 CH 3 CH3 CH 3 I
CH-I.
CH- rubinrotRuby red HH rotRed HH rotRed HH rotRed HH rotRed CHj-CHj- rubinrolrubinrol CH2-CH 2 - rubinrotRuby red

27 2827 28

ImIx-IIc')ImIx-IIc ')

(N K (N(N K (N

Cl NN-" ;· Ni i YCl NN- "; · Ni i Y

Nil XNile X

Nr K X Y l-'aibuinNr K X Y l-'aibuin

1X7 (,IU Il 1X7 (, IU Il

ISS C2IU H ISS C 2 IU H

1X4 C2IU H1X4 C 2 IU H

190 c,H5 Il190 c, H 5 Il

191 C2H5 Il 191 C 2 H 5 II

19: C2IU (CH2), O (CH2I4 OH19: C 2 IU (CH 2 ), O (CH 2 I 4 OH

193 C2IU CH2 CH CJU 193 C 2 IU CH 2 CH CJU

OHOH

194 (',!I, CII2 (H2 OH194 (',! I, CII 2 (H 2 OH

195 (',H5 CH2 CH, CH, - Oil 195 (', H 5 CH 2 CH, CH, - Oil

196 C2IU CH2 CII2 - CH2 OH 196 C 2 IU CH 2 CII 2 - CH 2 OH

197 C,H5 (H, CH2 OH197 C, 5 H (H, CH 2 OH

OC H, I9X L1H. CH2 CH, - OH --( "} orangeOC H, 19X L 1 H. CH 2 CH, - OH - ("} orange

IlIl gelbyellow CH3 CH 3 gelbyellow C2H.,C 2 H., gelbyellow CH2 CH2 OHCH 2 CH 2 OH gelbyellow (CH2), O (CHj)4 OH(CH 2), O (CHj) 4 OH gelbyellow HH gelbyellow HH gelbyellow I,I, gelbyellow HH gelbyellow C6H5 C 6 H 5 goldgelb bis
orangegolden yellow to
orange C6H5 C 6 H 5 goldgelb bis
orangegolden yellow to
orange

194194 C1H7 C 1 H 7 CH2 CH 2 CH2 - OHCH 2 - OH - CH2-CH2-C6H5 - CH 2 -CH 2 -C 6 H 5 TTTT gelbyellow 20(120 (1 C,H-C, H- - CH,- CH, CH2 -- OHCH 2 - OH - CH2- CH- C6H5
j- CH 2 - CH - C 6 H 5
j — Η- Η gelbyellow OHOH 201201 CH-CH- - CH2 -- CH 2 - C6H5 C 6 H 5 -■ CH, - CH2 — O — CH2 - CH2 — OH - ■ CH, - CH 2 - O - CH 2 - CH 2 - OH — CHj — C Hj — OH- CHj - C Hj - OH gelbyellow OHOH 202202 - C6H5 - C 6 H 5 -CH2--CH 2 - CH2 — O -- CH2 CH,CH 2 - O - CH 2 CH, OH - CH2 — CH2 OCH3 OH - CH 2 - CH 2 OCH 3 — CH2 - CHj - OH- CH 2 - CHj - OH gelbyellow 203203 -■ C,H7(n)- ■ C, H 7 (n) — CH2 -- CH 2 - CH2 — OHCH 2 - OH - (CH2), - O - (CHj)3 — O — QH5 - (CH 2 ), - O - (CHj) 3 - O - QH 5 — CH, — CHj - OH- CH, - CHj - OH gelbyellow 204204 - CH,(nl- CH, (nl — H- H — H- H gelbyellow 205205 — (C3H7(n)- (C 3 H 7 (n) -(CH2),- (CH 2 ), -0-(CHj)4-OH-0- (CHj) 4 -OH — CH, — CH, — CH, — OH- CH, - CH, - CH, - OH gelbyellow 206206 -C2H5 -C 2 H 5 UU — CHj - CHj - QH5 - CHj - CHj - QH 5 gelbyellow 207207 — C3H7(Ii)- C 3 H 7 (Ii) — H- H CH2 CH2 C^H5 CH2 CH 2 C ^ H 5 gelbyellow 208208 - C3H,(n)- C 3 H, (n) MM. -CH3-CH-QH5 -CH 3 -CH-QH 5 gelbyellow CH3 CH 3 209209 — C3H7(n)- C 3 H 7 (n) -CHj--CHj- CH2-QH5 CH 2 -QH 5 gelbyellow 210210 — C3H7(n)- C 3 H 7 (n) — CHj-- CHj- CH-QH5 CH-QH 5 gelbyellow CH3 CH 3 211211 -C3H7(D)-C 3 H 7 (D) -CH2--CH 2 - CH- Qu5 CH- Qu 5 gelbyellow CH3 CH 3 212212 — C3H7(n)- C 3 H 7 (n) CHjCHj CHj QH5 CHj QH 5 gelbyellow 213213 - C3H7(n)- C 3 H 7 (n) -CHj--CHj- CH - C6H5 CH - C 6 H 5 gelbyellow I
OH I.
OH

2929

iibelle IOiibelle IO

C N K CNC N K CN

■ N N ■■·' χ>· Nil V V- N ■ NN ■■ · 'χ> · Nil V V- N

Nil XNile X

51 702/051 702/0

Nr. KNo. K

lai'hlonlai'hlon

214214 i\iUi \ iU IlIl CH..CH .. OHOH 215215 ( ,Hin)( ,There) IlIl :i(.: i (. C1, H,C 1 , H, IlIl (II,(II, OilOil 217217 CII C4It,CII C 4 It, CU,CU, (II.(II. onon CII,CII, CH,CH, OilOil 21*21 * C1IMnIC 1 IMnI (II..(II .. 21 1J21 1 y (Ml-In)(Ml-In) CH,CH, 220220 CII-InICII-InI (II,(II,

(Ml,(Ml,

232232 -C3H7In)-C 3 H 7 In) 233233 -C3H7(H)-C 3 H 7 (H) 234234 -C3H7(Ii)-C 3 H 7 (Ii) 235235 -C3H7(Ii)-C 3 H 7 (Ii) 236236 — C3H7(Ii)- C 3 H 7 (Ii) 237237 — C3H7(Ii)- C 3 H 7 (Ii) 238238 - C3H7(Ii)- C 3 H 7 (Ii) 239239 -QH7(Ii)-QH 7 (Ii) !40! 40 - C3H7(Ii)- C 3 H 7 (Ii) S41S41 -QH5 -QH 5 •42• 42 — H- H !43! 43 — H- H

(II. CH, Oll(II. CH, Oll

-J--J- ( II,(II, (11,(11, CII,CII, OHOH OHOH 22'22 ' (MU(MU (II.(II. Cl;Cl; (II..(II .. onon 224224 CIUCIU (II,(II, C1I.C 1 I. Cl,Cl,

22:- (,!!-(»Ι CH, (H, CH, Oil22: - (, !! - (»Ι CH, (H, CH, Oil

J2(i C1H-(IiI CII, i'.l; O Cl, CiI, OHJ2 (i C 1 H- (IiI CII, i'.l; O Cl, CiI, OH

227 CMI, (Tl, ClI, O CII2 Cl, OH227 CMI, (Tl, ClI, O CII 2 Cl, OH

22,s CH, ( H, CH C, IU22, s CH, ( H, CH C, IU

I onI on

224 (MI-In) Cl, CH QHS 224 (MI-In) Cl, CH QH S.

OHOH

230 CH7In) CH, CH -■ C1JU 230 CH 7 In) CH, CH - ■ C 1 JU

OHOH

231 — C3H7(Ii) - CH, - CH -- QH, 231 - C 3 H 7 (Ii) - CH, - CH - QH,

OH -(CH2)J-O-(CHj)4-OHOH - (CH 2 ) JO- (CHj) 4 -OH

— H- H

— CH2 — CH2 - CHj - OH - CH 2 - CH 2 - CHj - OH

— H- H

— H- H

— CHj — CHj — OH- CHj - CHj - OH

— CHj — CH2 - CHj — OH C H2 CHj QH5 - CHj - CH 2 - CHj - OH CH 2 CHj QH 5

-CH2-CHj-QH,-CH 2 -CHj-QH,

-CH2-CH2 -0-CH2-CH2-OH-CH 2 -CH 2 -0-CH 2 -CH 2 -OH

— CH2 — CH2 - OH- CH 2 - CH 2 - OH

— CH2 — CH2 - OH- CH 2 - CH 2 - OH

IlIl CH,CH, (,.H,(,.H, IlIl (Il(Il c,,H,c ,, H, IlIl OHOH IlIl CHCH ciuciu IlIl OHOH (II,(II, CH2 CH 2 C,. H,C ,. H, (Tl,(Tl, Cl,Cl, CJUCJU ClCl CJUCJU CH,CH, OHOH ClCl CJI.CJI. CII,CII, OHOH CHjCHj CU - CU - I „H?I "H? (II,(II, OHOH ( Il(Il C,, 115 C ,, 11 5 (M,(M, OHOH (H(H (.JU(.JU CH2 CH 2 (JiI(JiI CH - CH - QH,QH, CH, -CH, - OHOH CH,CH, OO CH,CH, CU2 CU 2 CH,CH,

grünsticliijzgi'll μιιίιΐΝΐιυΙιιμμοΙΙ griinslichiggcll μι-lhgrünsticliijzgi'll μιιίιΐΝΐιυΙιιμμοΙΙ grinishigcll μι-lh

μι,-lh μοΙΙι μι-lhμι, -lh μοΙΙι μι-lh

μι-Ibμι-Ib

gdhgdh

gelbyellow

gi-lhgi-lh

CH, CH2 OH iielbCH, CH 2 OH much

gelbyellow

— H - H.

— (CH2I3 — O — (CHj)4 — OH - (CH 2 I 3 - O - (CHj) 4 - OH

— (CHj)3 — O — (CHj)4 — OH
-CH2-CH2-QH5 - (CHj) 3 - O - (CHj) 4 - OH
-CH 2 -CH 2 -QH 5

CH2 QH5 CH 2 QH 5

-H-H

- CHj — CH2 — OH- CHj - CH 2 - OH

CHj - CH2-O-CH3 -CH2-CH2-QH5 CHj - CH 2 -O-CH 3 -CH 2 -CH 2 -QH 5

CH2-CH-QH.CH 2 -CH-QH.

gelbyellow

gelbyellow

gelbyellow

gelbyellow

gelbyellow

goldgelbgolden yellow

gold pel bgold pel b

gslbgslb

gelbyellow

gelbyellow

gelbyellow

Fortsetzungcontinuation

3131

— Η- Η

245245 - C3H,(n)- C 3 H, (n) 246246 — C3H7(n)- C 3 H 7 (n) 247247 - C3H7(n)- C 3 H 7 (n)

-CH2-CH-QH5 -CH 2 -CH-QH 5

OHOH

— CH2 — CH2 — O — COCH2 — C4H5 - CH 2 - CH 2 - O - COCH 2 - C 4 H 5

- CH2 - CH2 - O - CH2: - CH2 - OCHO -C2H5 - CH 2 - CH 2 - O - CH 2: - CH 2 - OCHO - C 2 H 5

3232

FarbionColor ion

— CH2 — CH; — 0 — CH2 — CH2 — OH gelb- CH 2 - CH; - 0 - CH 2 - CH 2 - OH yellow

CH2 — CH2 — CH2 — OCHO
C2H5 CH 2 - CH 2 - CH 2 - OCHO
C 2 H 5

gelb gelb gelbyellow yellow yellow

Tabelle 1!Table 1!

SO,' XN■-- N ~-f %— NH-Y NH-XSO, ' X N n - N ~ -f % - NH-Y NH-X

Farbtonhue

248248 - C2H5 - C 2 H 5 - H- H CH2 -OHCH 2 -OH -OH-OH — H- H CH2 OHCH 2 OH 249249 C3H7In)C 3 H 7 In) — H- H -H-H CH2 ■- O — CH3 CH 2 ■ - O - CH 3 250250 - C,H7(nl- C, H 7 (nl - CH2 -- CH 2 - CH2-O-CH2-CH2 CH 2 -O-CH 2 -CH 2 - H- H -OH-OH 251251 - C3H7In)- C 3 H 7 In) — H- H -OH-OH CH2 —CH 2 - -OH-OH 252252 - C3H7In)- C 3 H 7 In) -CH2--CH 2 - — OHIn)- OHIn) - CH2 -- CH 2 - — OH- OH 253253 — C3H7(n)- C 3 H 7 (n) -(CH2I3 - (CH 2 I 3 - OH- OH - (CH2).,- (CH 2 )., 254254 - C3H7In)- C 3 H 7 In) -(CH2),,- (CH 2 ) ,, O - (CH2I2 - OHO - (CH 2 I 2 - OH - (CHj)3 - (CHj) 3 255255 C3H7In)C 3 H 7 In) (CH2).,(CH 2 )., (CH2I2 (CH 2 I 2 256256 C1H7In)C 1 H 7 In) - (CH2I2 - (CH 2 I 2 - C2H5 - C 2 H 5

gelb gelb gelb gelb gelb gelb gelb gelb nclbyellow yellow yellow yellow yellow yellow yellow yellow nclb

TabelleTabel

N NN N

CNCN

N NN N

>N NH X> N NH X

NIINII

larbtonlarbton

257257 HH HH IlIl OHOH HH HH HH mtstichiggclbmtstichiggclb 258258 C2H5 C 2 H 5 IIII IlIl OHOH IlIl HH HH rolslichiggelhrolslichiggelh 259259 C1H7In)C 1 H 7 In) IlIl IlIl OHOH IlIl HH IlIl rolstichiggclbrolstichiggclb 260260 CH7InICH 7 InI IlIl IlIl OHOH 1111th CH3 CH 3 orangeorange 261261 C2H5 C 2 H 5 HH 1111th HH hi,Hi, orangeorange 262262 C2H5 C 2 H 5 IlIl HH IlIl OCH,OCH, CH II,CH II, hliiiislii'lugi'oihliiiislii'lugi'oi 263263 C2H5 C 2 H 5 IIII IlIl HH OCH,OCH, CH,CH, ScharlachScarlet fever 264264 C2H,C 2 H, CH2CH2C)IICH 2 CH 2 C) II ClI2C H2 ClI 2 CH 2 IlIl IlIl HH TOlTOl 265265 C2H5 C 2 H 5 C H2C H2OIICH 2 CH 2 OII C IUH2 C IUH 2 NO,NO, IlIl IlIl bordobordo 266266 CH2CH2OHCH 2 CH 2 OH CH2CH2 CH 2 CH 2 IlIl OCH,OCH, CH,CH, hliiustii'higroihliiustii'higroi 267267 CH5 CH 5 C II,CH1OIIC II, CH 1 OII CIU II,CIU II, ClCl IlIl CII,CII, gi'lhstK'higroigi'lhstK'higroi

Tabelle 13Table 13

3333

n=Nn = N

/ Vn=N-/ Vn =/ Vn = N- / Vn =

n =n =

R CNR CN

nh-ynh-y

NH-XNH-X

3434

Farbtonhue

— H —H- H —H

— CH2 — CH2 — OH — H- CH 2 - CH 2 - OH - H

— CH2 — CH2 — OH — H -CH3-CH2-OCH2-CH2-OH — H- CH 2 - CH 2 - OH - H -CH 3 -CH 2 -OCH 2 -CH 2 -OH - H

268 —Η —Br —Br —H268 —Η —Br —Br —H

269 -C2H5 —Br —Br —Η269 -C 2 H 5 -Br -Br -Η

270 -C2H5 —CN —CN — H270 -C 2 H 5 -CN-CN-H

271 -C2H5 —CN —CN —H 372 -C3H5 -CH3 —Br — H $73 -C2H5 -CH, —CN -H $74 -C2H5 -CH, —CN — H $75 -C2H5 -CH3 —CN — H $76 -C2H5 — H — H — H271 -C 2 H 5 —CN —CN —H 372 -C 3 H 5 -CH 3 —Br - H $ 73 -C 2 H 5 -CH, —CN -H $ 74 -C 2 H 5 -CH, —CN - H $ 75 -C 2 H 5 -CH 3 -CN-H $ 76 -C 2 H 5 -H-H-H

$77 -C2H5 —Br —Br -CHj-CH2-OH -CH2-CH2-OH$ 77 -C 2 H 5 -Br -Br -CHJ-CH 2 -OH -CH 2 -CH 2 -OH

Tabelle 14
H3CO2CTable 14
H 3 CO 2 C

-CH2-CH2-OCH2-CH2-OH —Η -CH2-CH2-OCH2-CH2-OH —Η -CH2-CH2-OH —Η-CH 2 -CH 2 -OCH 2 -CH 2 -OH -Η -CH 2 -CH 2 -OCH 2 -CH 2 -OH -Η -CH 2 -CH 2 -OH -Η

-CH2-CH2-OH -Cl-CH 2 -CH 2 -OH -Cl

-CH2-CHj-OCHj-CHj-OH —Η-CH 2 -CHj-OCHj-CHj-OH -Η

— Η- Η

braungelbbrownish yellow

ScharlachScarlet fever

blaustichigrotbluish red

blaustichigrotbluish red

scharlachScarlet fever

rotRed

rotRed

rotRed

scharlachScarlet fever

rotRed

-N=N-N = N

CNCN

NH-YNH-Y

Farbtonhue

$78$ 78 -CjH5 -CjH 5 — Η- Η -O-O -(CHj)4-OH- (CHj) 4 -OH -(CH2 - (CH 2 I3-O-(CH2U-OHI 3 -O- (CH 2 U-OH gelbstichigroyellowish green $79$ 79 - CjH5 - CjH 5 — Η- Η — Ο- Ο -(CHj)4-OH- (CHj) 4 -OH )3 — O — (CH2)6 — OH) 3 - O - (CH 2 ) 6 - OH gclbstichigrogclbstichigro $80$ 80 -CjH5 -CjH 5 — Η- Η CHjCHj -OH-OH -CH2 -CH 2 -CH-C6H5 -CH-C 6 H 5 gelbstichigrolyellowishigrol CH2 CH 2 -OH-OH OHOH $81$ 81 "CjH7In)"CjH 7 In) — Η- Η -CH2 -CH 2 - CH - C6H5 - CH - C 6 H 5 gelbstichigrolyellowishigrol CH2 CH 2 -OH-OH OHOH 282282 - C1H7In)- C 1 H 7 In) - (CHj),- (CHj), — Η- Η gelbstichigrolyellowishigrol 283283 C1H7In)C 1 H 7 In) -(CHj),- (CHj), CH2 CH 2 OHOH -CH2 -CH 2 - CH2 — CH2 — OH- CH 2 - CH 2 - OH rotRed 284284 - C,H7(n)- C, H 7 (n) - CHj -- CHj - CH2 CH 2 OHOH -CH2 -CH 2 -CH2-C6H5 -CH 2 -C 6 H 5 rotRed 285285 ~ C1H7In)~ C 1 H 7 In) -CH. --CH. - CH2 CH 2 — CH2 OH- CH 2 OH -CH2 -CH 2 -CH-C6H5 -CH-C 6 H 5 rotRed CH,CH, 286286 CjH5 CjH 5 - C Hj -- C Hj - CH2 CH 2 OHOH -CHj-CHj -CH-C6H,-CH-C 6 H, rotRed CHjCHj OHOH CH3 CH 3 287287 (j H5 (j H 5 CH2-CH 2 - (H2 (H 2 O (H2 (H2 O (H 2 (H 2 (CH2 (CH 2 ,-0-(CH2)J-O-C6H5 , -0- (CH 2 ) JOC 6 H 5 rotRed 288288 C3H7In)C 3 H 7 In) CH2 -CH 2 - CHjCHj OHOH (CH2 (CH 2 3-O-(CHj)j -O -C6H5 3 -O- (CHj) j -O -C 6 H 5 ro!ro! 289289 C1H7In)C 1 H 7 In) (H2-(H 2 - CHjCHj -CH-C6H5 -CH-C 6 H 5 rotRed CH;CH; OHOH OHOH 290290 CjH7In)CjH 7 In) CH2 CH 2 C6H5 C 6 H 5 rotRed 291291 CjH,CjH, CH2 CH 2 CII2 CII 2 C6II5 C 6 II 5 C6IUC 6 IU rotRed 292292 C5H11In)C 5 H 11 In) CH2 CH 2 (H,(H, (,,IU(,, IU OH CH2 OH CH 2 CW7 O CW1 CW 7 O CW 1 rotRed 293293 C1H7In)C 1 H 7 In) (H2 (H 2 CH2 CH 2 Ch2 CH C,, H,Ch 2 CH C ,, H, rotRed CH1 CH 1 CH,
CII1 CH,
CII 1 294294 C1H7In)C 1 H 7 In) CH2 CH 2 I
CHI.
CH (CH2I1 C OH(CH 2 I 1 C OH I OlI ol CH,CH, 295295 ( ,1I7(HI(, 1I 7 (HI (H2 (H 2 IlIl gclbstichigrogclbstichigro 29(ι29 (ι CjIUCjIU (H,(H, IlIl gclbstichigrogclbstichigro

Tabelle 15Table 15

CH3O R CNCH 3 OR CN

N -^- NN - ^ - N

-NH-Y-NH-Y

NH-XNH-X

3636

Farbtonhue

QH3 QH 3

-QH,-QH,

- QH5 - QH 5

3IX)3IX) - QH7(n)- QH 7 (n) 301301 - QH1(Ii)- QH 1 (Ii) 302302 -QH7(n)-QH 7 (n) 303303 -QH,-QH, 304304 -QH,-QH, 305305 -QH5 -QH 5 306306 - QH5 - QH 5 307307 — QH,- QH, 308308 -C)H7In)-C) H 7 In) 309309 — Η- Η 310310 -- H-- H

— H- H

313313 C1H1(Ii)C 1 H 1 (Ii) 314314 --QH1(Ii)--QH 1 (Ii) 315315 -QH1(Ii)-QH 1 (Ii) 316316 - C2H,- C 2 H, 317317 QH,QH, 318318 --QH1(Ii)--QH 1 (Ii) 319319 QH1(Ii)QH 1 (Ii) 320320 QH,QH, 321321 QH,QH, 322322 C„H,C "H, J23J23 C2H,C 2 H, 324324 CjI-Mn)CjI-Mn) 325325 ('.,!Mn)('.,! Mn) 32()32 () C3H1(Ii)C 3 H 1 (Ii) 327327 (',!I1In)(',! I 1 In) 32 S32 p C1IMmC 1 IMm

— Η
-CH2-CH2-OH- Η
-CH 2 -CH 2 -OH

— CH2 — CH2 - CH2 — OH- CH 2 - CH 2 - CH 2 - OH

— CH2 — CH2 — CH2 — OH- CH 2 - CH 2 - CH 2 - OH

— CH2 — CH2 — OH -H- CH 2 - CH 2 - OH -H

-CH2-CH2-OH -CH2-CH2-OH-CH 2 -CH 2 -OH -CH 2 -CH 2 -OH

— CH2 — CH2 — OH -CH2-CH2-OH- CH 2 - CH 2 - OH -CH 2 -CH 2 -OH

— (CH2), - O — (CH2I2 — O - QH5 - (CH 2 ), - O - (CH 2 I 2 - O - QH 5

— (CHj)3 - O - (CH2I2 -O- QH5 - (CHj) 3 - O - (CH 2 I 2 -O- QH 5

— (CHj)3 - O - (CHj)2 — O - QH,- (CHj) 3 - O - (CHj) 2 - O - QH,

— CH2 - CH2 — Ol 1- CH 2 - CH 2 - Ol 1

-CH2-CH2 — OH-CH 2 -CH 2 - OH

— (CH2)., - OH- (CH 2 )., - OH

-CH2-CH2-CH2-Ch2-CH2-CH2OH -CH2 -CH-QH5 -CH 2 -CH 2 -CH 2 -Ch 2 -CH 2 -CH 2 OH -CH 2 -CH-QH 5

-CHj-CH-C0H,-CHj-CH-C 0 H, gelbstichigrotyellowish red OHOH -CH2-CH- QH5 -CH 2 -CH- QH 5 gelbstichigrotyellowish red OHOH CH2-CH-QH5 CH 2 -CH-QH 5 gelbstichig rotyellowish red OHOH -CH2-CH-QH5 -CH 2 -CH-QH 5 gelbslichigrotyellowish red OHOH CH2-CH-C6H,CH 2 -CH-C 6 H, gelbstichigiotyellowish tint OHOH -CH2- CH- QH,-CH 2 - CH- QH, gclbstichigrotyellow-tinted red OHOH -CHj-CH2-QH5 -CHj-CH 2 -QH 5 rotRed - QH5 - QH 5 rolrol - (CHj)3 -O- (CH2I2 -O- QH5 - (CHj) 3 -O- (CH 2 I 2 -O- QH 5 rotRed - (CH2J3 — 0 — (CH2J2 -- O - C6H5 - (CH 2 Y 3 - 0 - (CH 2 J 2 - O - C 6 H 5 rotRed -(CHj)2-OH- (CHj) 2 -OH rotRed -(CHj)2-OH- (CHj) 2 -OH rotRed -(CH2),— OH- (CH 2 ), - OH gelbstichigrotyellowish red -CH2-CH-C6H5 -CH 2 -CH-C 6 H 5 rotRed CH3 CH 3 -CH2-CH-C6H5
ι-CH 2 -CH-C 6 H 5
ι rotRed I
OHI.
OH — CH2-(- CH 2 - ( rotRed ΓΗ — C4H5 ΓΗ - C 4 H 5

OH
-CH2-CHJ-CHJ-CH2-CHjCHjOHOH
-CH 2 -CHJ-CHJ-CH 2 -CHjCHjOH

OHOH - ic-- ic- Hj)4 Hj) 4 OHOH H2 H 2 OHOH - H- H H2 H 2 CH2 CH 2 11 - CH2 -- CH 2 - -OH-OH (CHj)j(CHj) j - O- O icic H2I4 H 2 I 4 OHOH Ή,Ή, OHOH -H-H H2 H 2 CH2 CH 2 -■ CH2 -- ■ CH 2 - -OH-OH - (CH2).,- (CH 2 )., OO - (C- (C Hj)4 Hj) 4 OHOH H2 H 2 OHOH CC. -H2I.,-H 2 I., - 0- 0 (CH2I4 (CH 2 I 4 — OH- OH (CH2),(CH 2 ), -■ ο- ■ ο -(C- (C Hj)4 Hj) 4 OHOH H2 H 2 OHOH CC. H2),H 2 ), OO -(CH2U- (CH 2 U OHOH - (CHj)3 - (CHj) 3 OO -H2 -H 2 OHOH (C(C. H2 H 2 CH2 CH 2 - CH2 -- CH 2 - OCHOOCHO HH H2 H 2 OHOH - ((- (( H2 H 2 CH2 CH 2 OCOC H,H, HH -IC-IC H2I4 H 2 I 4 H,H, OHOH CC. H2 H 2 CH;CH; Ο —CΟ —C H,H, (CHj),(CHj), OO OO CC. CC. H2 H 2 CH2 CH 2 O CO C "H,"H, CH2 CH 2 VH2 VH 2 OO (( CC. H2 H 2 CH,CH, (ΊΙ,(ΊΙ, OCH,OCH, CH2 CH 2 CHjCHj OO CC. CC. H /H / CH2 CH 2 CH2 CH 2 OO CC. CC. 2 Π,2 Π, CH2 CH 2 CHjCHj OO CC. \
\\
\ .1Un.1Un CH2 CH 2 CH;CH; OO ιι ■■■ C■■■ C CH;CH; (H;(H; OO (( OCHOOCHO (( CH,CH, C!lC! L H2 CH 2 C Ή; CΉ; C. Ή; CΉ; C. M2 (M 2 ( H2 CH 2 C H2 CH 2 C II, (II, (

rot
gelbstichigrotRed
yellowish red

gelbstichigrotyellowish red

gclbstichigrotyellow-tinted red

gelbstichigrotyellowish red

gelbstichigrotyellowish red

gelbstichigrotyellowish red

gclbstichigrotyellow-tinted red

gclbslichigrolgclbslichigrol

rolrol

rolrol

rolrol

rotRed

rol
rolrol
rol

Tabelle 16Table 16

NO, R CNNO, R CN

CN-* V-N N--<f ^-NH-Y Ci NH-XCN- * V-N N - <f ^ -NH-Y Ci NH-X

Nr.No.

3838

l-'arblonl-'arblon

J29J29 -C2H,-C 2 H, HH CH2 -CH 2 - OHOH OllOll C,.H,C, .H, ,Oll, Oll CC. CIlCIl OllOll Cn C n H,H, rolrol C, ,H,C,, H, OHOH 330330 - C2H5 - C 2 H 5 ~CH,~ CH, CII,CII, ClI;ClI; OHOH C',, 11,C ',, 11, CC. (11(11 Cn C n ,H5 , H 5 rolrol I
OH I.
OH 331331 C2H,C 2 H, -CH2 -CH 2 (11,(11, CH.CH. CC. CIICII C1,C 1 , H5 H 5 rolrol OllOll 332332 C1IUmC 1 IUm CII,CII, CH2 CH 2 OllOll CC. (H(H C1.C 1 . 11,11 mlml OllOll 333333 C1HMnIC 1 HMnI CH2 CH 2 CC. CIICII C1,C 1 , II.II. mlml [i,cn[i, cn OllOll 334334 C1HMnIC 1 HMnI ΠΠ cn.cn. OllOll OllOll CC. CIICII (■„(■ " H,H, rolrol cn.cn. onon OHOH OllOll OllOll 335335 C1WC 1 W CH,CH, OO OllOll CC. CH;CH; C,C, ,,II,,, II, nihinnihin 336336 C2H,C 2 H, CH,CH, CH2 CH 2 CH2 CH 2 OO olloll (( 337337 C2H,C 2 H, ■-II■ -II OO (CH2I2 (CH 2 I 2 OO OHOH KK ι. οι. ο «« H2I2 O („Π,H 2 I 2 O ("Π, rubinruby 338338 C2H,C 2 H, - cn.- cn. OO (CII2I.(CII 2 I. OllOll KK )-. O) -. O ICIC H2I2 O („11,H 2 I 2 O ("11, ι u binι u am 339339 C2H,C 2 H, - (CH2I,- (CH 2 I, C)-C) - (CH2I2 (CH 2 I 2 onon (C(C. ); Oll); Oll ι ti hin ι ti out 340340 C1H-(Ii)C 1 H- (Ii) ICH2).,I 2 )., CH2 CH 2 OHOH ICIC I2 OHI 2 OH riihinriihin 341341 IlIl -(CH2),- (CH 2 ), IoIo icic I2 OllI 2 Oll rubinruby 342342 HH CH2 CH 2 CH2 CH 2 OllOll Ή;Ή; CC. cncn C1,C 1 , II,II, ruhinRuhin 'H2 'H 2 cn,cn, ?43? 43 ππ C 11,C 11, OllOll H2 ClH 2 Cl H2 H 2 CC. cncn C1,C 1 , H5 H 5 rubinruby II,II, OHOH J44J44 HH (CII2).,(CII 2 )., CH2 (CH 2 ( 'Hj-C'Hj-C 11.111.1 CC. CWCW C1,C 1 , H5 H 5 rubinruby cn
ι cn
ι CnIl,C n Il, OHOH ■11.1■ 11.1 OllOll 545545 C1H-In)C 1 H-In) CH2 CH 2 OHOH OllOll II,II, CC. CH2CCH 2 C H2CH 2 C H2(Il2CH, OHH 2 (II 2 CH, OH rubinruby J4(iJ4 (i C1H7In)C 1 H 7 In) ClI2 ClI 2 OO (CH2I4 (CH 2 I 4 OHOH IlIl rolrol OO (CHiI4 (CHiI 4 OllOll J47J47 C jHMη IC jHMη I (CH2I,(CH 2 I, OO (CHi)4 (CHi) 4 IlIl rolrol J4XJ4X C2H,C 2 H, (cn,),(cn,), OO (CII2I4 (CII 2 I 4 IlIl rolrol 349349 C2H,C 2 H, (CH2).,(CH 2 )., OCIOCI CC. CH2 CH 2 CC. H, OllH, Oll rolrol 350350 C1HMn)C 1 HMn) (CII2).,(CII 2 )., H2 (H 2 ( CC. CW2 CW 2 CC. n, onn, on rolrol 351351 C1H7In)C 1 H 7 In) IlIl OO « H,)4 «H,) 4 H.· <H. · < (((( Ij °Ij ° ICIC Hj)4 OllHj) 4 Oll rolrol 352352 C2H,C 2 H, IlIl CII,CII, O (O ( II, (II, ( KK I1 OI 1 O (C(C. H2I4 OHH 2 I 4 OH nilNile 353353 C2II,C 2 II, (CH2I,(CH 2 I, (II,(II, O (O ( II. (II. ( CC. ClI;ClI; CC. II, OCHIIII, OCHII rolrol 354354 („II,("II, CII,CII, CH1 CH 1 O (O ( 11, (11, ( CC. < H,<H, OO eil,hurry, rolrol 355355 C2II,C 2 II, CII2 CII 2 CII2 CII 2 O (O ( II, (II, ( CC. ( H2 (H 2 OO ( H1 (H 1 rolrol 35(i35 (i C1IUn)C 1 IUn) cn,cn, CH2 CH 2 O (O ( II, <II, < (( (II,(II, OO 111,111, IMlIMl 3^3 ^ C1IUnIC 1 IUnI ei !.ιei! .ι cn,cn, O (O ( CC. ( II.(II. CC. H2 OClI,H 2 OClI, mlml 35X35X C1II miC 1 II mi cw.cw. CH,CH, ( I ((I ( rolrol 159159 C1IUi)IC 1 IUi) I (II,(II, CC. rolrol 360360 C1IUiHC 1 IUiH CIl,CIl, C.C. rotRed 'H2 'H 2 H,H, H;H; H-H- H;H; H:H: H2 H 2 „ii-"Ii- H,H, 'H2 'H 2 'H2 'H 2 'H2 'H 2 H2 H 2 HjHj HjHj H,H, H2 H 2 H2 H 2 H,H, HjHj Ή,Ή, H2 H 2 H,H, 11,11 II.·II. H,H, HH ,11,, 11, ,11,,, 11 ,,

Tabelle 17Table 17

O,NO, N

3939

K (NK (N

N NN N

■ N Nil \■ N Nil \

Nil YNile Y

4040

Ni RNi R

larbtor.larbtor.

ViIViI HH ,H,,H, RR. CC. H, (H, ( Ή,Ή, OHOH OHOH OHOH C1 C 1 ,H,,H, (J(J (C(C. H2I4 H 2 I 4 OHOH blaublue id:id: IlIl .11,.11, ■ \ N ■■ \ N ■ CC. H, (H, ( H,H, CH.,CH., CH2 CII,CH 2 CII, OHOH C1 C 1 ,11,, 11, (J(J (C(C. H214 H 2 1 4 OHOH blaublue ViIViI IlIl ,11,, 11, CC. H, (H, ( H,H, OO (H2 (H;(H 2 (H; C1 C 1 .H-,.H-, CH2 CH 2 CC. H2 H 2 OHOH blaublue V.4V.4 (( ,H,,H, CC. II; (II; ( 1H.. 1 H .. OO OHOH C1 C 1 „Us"Us OO (((( "H2I2 "H 2 I 2 0 C11H,0 C 11 H, blaublue Vi^Vi ^ (( ,H-InI, H-InI CC. H, (H, ( H;H; (H;(H; C1 C 1 „Us"Us OO (C(C. H2I4 H 2 I 4 OHOH blaublue IM.IN THE. CC. ,H-InI, H-InI CC. II.· <■II. · <■ H..H.. OHOH OHOH C1 C 1 ,.IU, .IU blaublue 3(i73 (i7 CC. ,H-lnl, H-lnl CC. II; (II; ( H;H; (H,(H, (JlI(JlI (C(C. H2),H 2 ), rotstichigblaureddish blue 3(,X3 (, X (( ,H (nl, H (nl CC. H, (H, ( H,H, CH2 CH 2 :>4 OH:> 4 OH (C(C. TI2I,TI 2 I, rolstichigblauroller-tinged blue Vi1IVi 1 I (( ,H-(IiI, H- (IiI KK 11,1,11.1, OO (CH;(CH; OHOH CC. H,H, rolstichigblauroller-tinged blue 17(117 (1 CC. CC. H; (H; ( H;H; (H;(H; (((( "H2I3 "H 2 I 3 rotstichipblaured-tinted blue 171171 (( IlIl .I1, OH.I 1 , OH KK -HjIi-HjIi violettviolet 37:37: 11 ICIC H.I,HI, OO (CH;(CH; HH violettviolet TabelleTabel ISIS ( N(N I ),NIN NHNH YY ■ N■ N

NH XNH X

Farbtonhue

373373 C1H-In)C 1 H-In) rN
A rN
A. N = NN = N RR. R
\R.
\ CH;CH; CH; O CH,CH; O CH, CH,CH, CJH CH,CJH CH, (H,(H, OCH,OCH, CHj-CHj- rubinruby 374374 C2H,C 2 H, — H- H CH;CH; CH2 CJ CH;CH 2 CJ CH; CH;CH; OH — IH,OH - IH, CH2 CH 2 OCH,OCH, rubinruby 37?37? C2 H,C 2 H, — H- H ICH2I,I 2 I, O K H2I4 -OKH 2 I 4 - OHOH CH,CH, CH2 CH 2 OCH,OCH, rubinruby 37(i37 (i C7H,C 7 H, — H- H 1(11,1,1 (11.1, O ICH,»; --O I, »; - OHOH C2H,C 2 H, CHj-CHj- rubinruby 377377 C3H-InIC 3 H-InI -C2H5 -C 2 H 5 ICH,!,I,!, O ICH,!,O ME!, OHOH C2H,C 2 H, -QH5 -QH 5 rubinruby 37«37 « C3H-ImC 3 H-Im -C2H5 -C 2 H 5 (CH2I3 (CH 2 I 3 — (J - (CH2I4 -- (J - (CH 2 I 4 - OHOH - CH;- CH; CH;CH; CH; OHCH; OH rubinruby 379379 C3H-ImC 3 H-Im (C H; I, (CH; I, O - (CH2I4 -O - (CH 2 I 4 - CJHCJH HH rotRed 3S(I3S (I -C3H-InI-C 3 H-InI -(CH;);- (CH;); O - (CH2I; -O - (CH 2 I; - OHOH ■- H■ - H -OCH3 -OCH 3 rotRed 381381 — C3H7In) - C 3 H 7 In) — H- H -,CHjij-, CHjij — O- O (CH2U-OH(CH 2 U-OH rotRed Tabelle 19Table 19 CN
/ CN
/ /
Q2N /
Q 2 N V-NH-
>=NV-NH-
> = N -Y-Y //
NH-XNH-X Nr.No. YY Farbtonhue 382382 -(CHj)JO-(CHj)J-OH- (CHj) JO- (CHj) J-OH rotRed 383383 CH2 — OH CH 2 - OH -CH2--CH 2 - rot violettred purple 384384 CH2 — OH CH 2 - OH C6H5 C 6 H 5 violettviolet 385385 - O-<CH2)2-- O- <CH 2 ) 2 - OHOH — H- H rotRed 386386 -O —(CHj)2- -O - (CHj) 2 - OHOH -CH2--CH 2 - rotviolettred-violet XX — H- H -CHj--CHj- -CHj--CHj- -(CHj)J-- (CHj) J- -(CHj),- (CHj),

Nr RNo. R

,H,,H,

3XX3XX (( : 21K: 2 1K 3X93X9 (( 39(139 (1 (( '.,H-(IiI'., H- (IiI 391391 (( ,H-(Hi, H- (Hi 392392 (( '.,!!-(η)'., !! - (η) 393393 (( JKlnlJKlnl 394394 (( JI7(Il)JI 7 (Il)

(■(■

Tabelle 20
λ sTable 20
λ s

N \
SN \
S.

4141

(CIKl, O ICH,)(CIKl, O I,)

CII, CH, OHCII, CH, OH

CIK (H, OHCIK (H, OH

(IK (H, OH(IK (H, OH

CII2 (H2 OHCII 2 (H 2 OH

CH2 ClI, OHCH 2 ClI, OH

IlIl

CIK C\{, OHCIK C \ {, OH

ICH2I, 0-(CH2),I 2 I, 0- (CH 2 ),

OHOH

CNCN

NH γNH γ

4242

CH,CH,

C1JK
cl1· C 1 JK
cl1

cn,
CH,
CII,
CU cn,
CH,
CII,
CU

c„IK
(,JKc "IK
(, JK

OllOll

O KII,), () ,( ,
O (ClK)2 OO KII,), (), (,
O (ClK) 2 O

CII C11H,CII C 11 H,

(II,(II,

CH C„H,CH C "H,

CH,CH,

l-'arblonl-'arblon

lolviolcll lolviolcll rotviolcli rotviolctl lolviolcll lolviolcll rotviolcli rotviolctl

OCH1 rolviolcllOCH 1 rolviolcll

IU rolviolcllIU rolviolcll

rolviolcllrolviolcll

rolviolcllrolviolcll

rotviolclired violcli

N1H λN 1 H λ

!■arbton! ■ arbton

39(,39 (, CH,CH, 39 739 7 CII1 CII 1 19K19K CH,CH, 199199 CH.CH.

ClKOC CH2 CH, OClKOC CH 2 CH, O

CH3UC, H4OC — CHj — CH2 O CH 3 UC, H 4 OC - CHj - CH 2 O

Il CH3OC2H1OC — CHj — CH2 —II CH 3 OC 2 H 1 OC - CHj - CH 2 -

IiIi

CH3OC2H4OC — CH2CH2 —CH 3 OC 2 H 4 OC - CH 2 CH 2 -

Il CH3OCjHUOC — CH2 — CH2 — II CH 3 OCjHUOC - CH 2 - CH 2 -

IlIl

CH3OC2H4OC — CH2 — CHj — OCH 3 OC 2 H 4 OC - CH 2 - CHj - O

IlIl

CH3OC2H4OC — CH2 - CH2 — CH3OCOCH2CH2-CH 3 OC 2 H 4 OC - CH 2 - CH 2 - CH 3 OCOCH 2 CH 2 -

C2H5 C 2 H 5

' ClK CiI2 OH'ClK CiI 2 OH

CH2 CH2-OHCH 2 CH 2 -OH

CH, CH2 OHCH, CH 2 OH

<-'H2 CH2 OH<- 'H 2 CH 2 OH

t'H. CH2 OHt'H. CH 2 OH

(11,(11, CH2 CH 2 CC. '.JK'.JK orangeorange CfI2-CfI 2 - - cn -- cn - C1 C 1 .H5 .H 5 orangeorange OHOH CH,CH, CH -
I CH -
I. QQ JKJK orange-orange- OHOH CH2 CH 2 CH -
[ CH -
[ QQ H5 H 5 orangeorange OHOH

™ - CH2 C„H5 ™ - CH 2 C "H 5

- C3H7(H) - CH2 - CH2 - OH - CH2 — CH2 - QH5 - C 3 H 7 (H) - CH 2 - CH 2 - OH - CH 2 - CH 2 - QH 5

-C2H5 -CH2 CH2-OH -CH2-CH2-QH5 -C 2 H 5 -CH 2 CH 2 -OH -CH 2 -CH 2 -QH 5

-C2H5 -CH2-CH2 OH -QH5 -C 2 H 5 -CH 2 -CH 2 OH -QH 5

— C3H7(n) -CH2-CH2-OH -C6H5 - C 3 H 7 (n) -CH 2 -CH 2 -OH -C 6 H 5

— C3H7Oi) -CH2-CH2-CH2OH -QH5 - C 3 H 7 Oi) -CH 2 -CH 2 -CH 2 OH -QH 5

— C3H7(n) - CH2CHjCHjOH - CH2 — CH2 — QH5
-C3H7(H) -CHj-CH3-OH -CH2-CH-QH5 - C 3 H 7 (n) - CH 2 CHjCHjOH - CH 2 - CH 2 - QH 5
-C 3 H 7 (H) -CHj-CH 3 -OH -CH 2 -CH-QH 5

CH,CH,

orangeorange

orangeorange

orangeorange

orangeorange

orangeorange

orangeorange

orange orangeorange orange

4444

'Onset/u ημ'Onset / u ημ

Farbtonhue

4(IX4 (IX ( H1OCOCH2CH.,(H 1 OCOCH 2 CH., AA. -CONHCH,-CONHCH, C2HaC 2 Ha YY C ,C, A2 A 2 H1In) CH 1 In) C II.. CW1 OH |C H1 II .. CW 1 OH | C H 1 ),OKII2)., O QH5 ), OKII 2 )., O QH 5 CH2CH2QH5 CH 2 CH 2 QH 5 orangeorange 4IW4IW CHjOC(K1H2CH2 CHjOC (K 1 H 2 CH 2 - CONHCH,- CONHCH, C2H4 C 2 H 4 CjCj -H-H IMnI CIMnI C II., UK (JII CH,II., UK (JII CH, (H2 OCH,(H 2 OCH, -CH2CH2QH5 -CH 2 CH 2 QH 5 orangeorange 41114111 CHj(K1OCH2CH2 CHj (K 1 OCH 2 CH 2 CONHCH,CONHCH, A1 A 1 IlIl -Br-Br CC. \l, (H1 OH CW2 \ l, (H 1 OH CW 2 CII2 OCH,CII 2 OCH, -CH2-CH2QH5 -CH 2 -CH 2 QH 5 orangeorange OO
IjIj -SO2NH-C2H,-SO 2 NH-C 2 H, NN — Η - Η -Cl-Cl CH2 CH QH5 CH 2 CH QH 5 41 141 1 CH1OC C2H1 CH 1 OC C 2 H 1
OO -NH--NH- - Br - Br IlIl -Cl-Cl CC. H2 CH2 OH CH2 H 2 CH 2 OH CH 2 CH2 (KII,CH 2 (KII, OHOH orangeorange 4i:4i: ÜÜ
(H1K2H4O C(H 1 K 2 H 4 OC - SO2NH - C2H5 - SO 2 NH - C 2 H 5 -Cl-Cl HH CC. H2 ( H2 Oll CH2 H 2 (H 2 OII CH 2 CH2 OCH,CH 2 OCH, -CH2-CH-QH5 -CH 2 -CH-QH 5 orangeorange O
I] O
I] - Cl- Cl -Br-Br OHOH 41.141.1 I1 I 1
( 11,OK2II4O)2C(11, OK 2 II 4 O) 2 C
OO - SO2NH — C2H5 - SO 2 NH - C 2 H 5 HH CC. H2 CH2 OH CH2 H 2 CH 2 OH CH 2 — CH2 CX Η, - CH 2 CX Η, -CH2CH2OCH3 -CH 2 CH 2 OCH 3 orangeorange 414414 Ji
C H1C,C2Il4O)2C Ji
CH 1 C, C 2 II 4 O) 2 C SO2NH-C4 Η,(η) SO 2 NH- C 4 Η, (η) — Br- Br C1 C 1 -Br-Br Η7(η| CΗ 7 (η | C H2 C H2 OH CH2 H 2 CH 2 OH CH 2 CH2 -- OCH,CH 2 - OCH, -CH2CH2OCH3 -CH 2 CH 2 OCH 3 orangeorange TabelleTabel 2121 — SO2NH — QH,(n) - SO 2 NH - QH, (n) -Cl-Cl -CH2CH-QH5 -CH 2 CH-QH 5 A' R CA 'R C
\ /\ / — Br- Br -Cl-Cl OHOH Λ \Λ \ V-N - N-/ VV-N - N- / V — CONHQH9(Ii) - CONHQH 9 (Ii) — α- α -CH2CH-QH5 -CH 2 CH-QH 5 A2 N H - >A 2 NH -> -Cl-Cl -Cl-Cl II.
OHOH Nr.No. — C0NHQH,(n) - C0NHQH, (n) RR. XX YY -CH2CH-QH5 -CH 2 CH-QH 5 Farbtonhue 415415 —σ—Σ -Br-Br "C3H7In)"C 3 H 7 In) -CH2-CH2OH-CH 2 -CH 2 OH OHOH gelbyellow 416416 — CONHQH,(n)- CONHQH, (n) -C3H7In)-C 3 H 7 In) - CH2-CH2OH- CH 2 -CH 2 OH -CH2-CH-QH5 -CH 2 -CH-QH 5 rotstichiggell:rotstichiggell: 417417 -Br-Br -Br-Br -C3H7In)-C 3 H 7 In) -CH2-CH2OH.-CH 2 -CH 2 OH. OHOH rotstichiggelbreddish yellow 41»41 » — CONHQK13 - CONHQK 13 QH7In)QH 7 In) -CH2-CH2OH-CH 2 -CH 2 OH -CH2CH2OH-CH 2 CH 2 OH orangeorange -CONH-QHn(I)-CONH-QH n (I) -Br-Br — σ- σ -CH2CH2OH-CH 2 CH 2 OH 414414 -CONHQH17(I)-CONHQH 17 (I) —α—Α -C3H7(Ii)-C 3 H 7 (Ii) — CH2 — CH2 — OH- CH 2 - CH 2 - OH -CH2CH2OH-CH 2 CH 2 OH orangeorange -SO2NHQH,-SO 2 NHQH, -Ci-Ci -Br-Br -CH2CH-QH5 -CH 2 CH-QH 5 420420 — σ- σ — Η- Η -QH7(Ii)-QH 7 (Ii) — (CH2)2O(CH2)2OH- (CH 2 ) 2 O (CH 2 ) 2 OH orangeorange 421421 O-
DIO-
Tue L2H5 L 2 H 5 -(CH2I2O(CH2I2OH- (CH 2 I 2 O (CH 2 I 2 OH orangeorange 422422 — Η- Η C2H5 C 2 H 5 -CH2CH2OH-CH 2 CH 2 OH orangeorange «23«23 -C2H5 -C 2 H 5 -CH2CH2OH-CH 2 CH 2 OH rotstichiggelbreddish yellow 124124 -QH5 -QH 5 -CH2CH2OH-CH 2 CH 2 OH rotstichiggelbreddish yellow «25«25 -C3H7In)-C 3 H 7 In) — CH2CH2OH- CH 2 CH 2 OH rotstichiggelbreddish yellow »26»26 -QH7(n)-QH 7 (n) -CH2CH2OH-CH 2 CH 2 OH rotstichiggelbreddish yellow 127127 -QH7(n)-QH 7 (n) -CH2CH2OH-CH 2 CH 2 OH rotstichiggelbreddish yellow 128128 -QH7(n)-QH 7 (n) -CH2CH2OH-CH 2 CH 2 OH rotstichiggelbreddish yellow 129129 -QH,(n)-QH, (n) -CH2CH2OH-CH 2 CH 2 OH gelbyellow

OHOH

Ti1 belle 22Ti 1 belle 22

CH1 R CNCH 1 R CN

O2N <;" Χϊ· Ν Ν <ζ · Nil Y NH XO 2 N <;" Χϊ · Ν Ν <ζ · Nil Y NH X

4646

l'arblonl'arblon

430430 IlIl HH "H2).."H 2 ) .. OO ICH.I. 431431 C2H5 C 2 H 5 IlIl H;H; (Il(Il C1,1UC 1 , 1U 43:43: C2IUC 2 IU IlIl OHOH 433433 C2H5 C 2 H 5 (((( H2 H 2 CU2 CU 2 CH2 CH 2 434434 C2H,C 2 H, CC. H2 H 2 CU2 CU 2 OHOH H2 H 2 (H2 (H 2 OHOH 435435 C2IUC 2 IU CC. H,H, CH,CH, OHOH 436436 C2IUC 2 IU (( 437437 C2IUC 2 IU CC. 4.IX4.IX C2IUC 2 IU CC.

C1IMnIC 1 IMnI

440440 C |1Μη)C | 1Μη) 441441 (.,HT(nl(., H T (nl 442442 C,H,(n)C, H, (n) 443443 C2H5 C 2 H 5 444444 C2H,C 2 H, 445445 C1Ht(P)C 1 Ht (P) 446446 C3H-In)C 3 H-In) 447447 -C3 H7(r.)-C 3 H 7 (r.) 44X44X C,H,(n)C, H, (n) 444444 C1H-InIC 1 H-InI 450450 C2H5 C 2 H 5 451451 - C,H,(n)- C, H, (n)

C2H5 C 2 H 5

453453 C2IUC 2 IU 454454 C2H5 C 2 H 5 455455 -QH5 -QH 5 TabelleTabel 2323 CNCN

(H2
CH2
(H,(H 2
CH 2
(H,

CM2 CU2 CH2 CH2 CM 2 CU 2 CH 2 CH 2

CII2 - CH2 CII 2 - CH 2

(CH2J3 - O(CH 2 J 3 - O

C2H,C 2 H,

.'CH2), O.'CH 2 ), O

OHOH

OHOH

CH, CII, OHCH, CII, OH

(II, (H2 OH (H2 (H, OH(II, (H 2 OH (H 2 (H, OH

OH OHOH OH

O CH, O ( O CH,O CH, O (O CH,

|C Hj)2- O-| C Hj) 2 - O-

(H, OH CH2 Oll CH, OH(H, OH CH 2 OII CH, OH

ICH2I4 OHI 2 I 4 OH

-CH, -CH- C„IU-CH, -CH- C "IU

OH -CH2- CH C„H5 OH -CH 2 - CH C "H 5

OHOH

- (CH2I2-O-(CHj)2 OCHO- (CH 2 I 2 -O- (CHj) 2 OCHO

- (CH2I2 — O — (CH2), - O - C(JCH1 - (CH 2 I 2 - O - (CH 2 ), - O - C (JCH 1

- (CHj)3 - O - (CHJ2 - O - QH,- (CHj) 3 - O - (CHJ 2 - O - QH,

CNCN

BrBr

NH-XNH-X

K H2), O
(CII2I1 OKH 2 ), O
(CII 2 I 1 O

CH. CUCH. CU

OHOH

(H,
CH2 (H,
CH 2

CII,CII,

(CH,
CH,(CH,
CH,

(',.H5
(V. H,(', .H 5
(V. H,

c*iuc * iu

C H2 C H 2

(CH2!(CH 2 !

CH2 CH 2

C2H5 C 2 H 5

CH2 CH 2

CH,CH,

ClIClI

OH
CIIOH
CII

OHOH

CHCH

CH1 CH 1

(CH2I4 Oll
KH2I4 Oll
(,,IU(CH 2 I 4 Oll
KH 2 I 4 Oll
(,, IU

CJU
(,,IU CJU
(,, IU

C11IUC 11 IU

(CH2I2 O
O C„IU(CH 2 I 2 O
OC "IU

C11H,C 11 H,

(H2 OCH1 (H 2 OCH 1

O CH(CH,),
CH, OHO CH (CH,),
CH, OH

- CH2 (II, OH
- CH, - O CH,- CH 2 (II, OH
- CH, - O CH,

CM2 OH CM 2 OH

CH, CU2 -O CH2 CH2 - OHCH, CU 2 -O CH 2 CH 2 - OH

-CH, - CH2OCH1 -CH, -CH 2 OCH 1

CH2-CH2 OCH3 CH 2 -CH 2 OCH 3

- CH2 — CH2 — OCH, - CH 2 - CH 2 - OCH,

5656 - H - H. — H - H. 5757 C2H5 C 2 H 5 5858 -C2H5 -C 2 H 5 — H - H.

— (CHj)3 - O — (CHj)4 — OH- (CHj) 3 - O - (CHj) 4 - OH

— (CH2), — O — (CHj)4 - OH -CH2-CH-QH5 - (CH 2 ), - O - (CHj) 4 - OH -CH 2 -CH-QH 5

OHOH

orange orange orangeorange orange orange

orange orangeorange orange

orange ontngeorange ontnge

rolstichigorungi rolslichigorangtrolstichigorungi rolslichigorangt

rotslichigorangireddish orangi

rolslichigorange rolstichigoriingcrolslichigorange rolstichigoriingc

ScharlachScarlet fever

ScharlachScarlet fever

ScharlachScarlet fever

orangeorange

orangeorange

orangeorange

orangeorange

gelbyellow

orangeorange

orangeorange

orangeorange

orange orange orange orange orange orange

FarbionColor ion

orange orange orangeorange orange orange

4747

Fortsetzungcontinuation

Nr. RNo. R

459459 -QH5 -QH 5 — (CH,).,- O-- (CH,)., - O- - (CH2U- (CH 2 U -OH-OH 460460 - QH5 - QH 5 -CH2-CH--CH 2 -CH- CH5 CH 5 OHOH 461461 -QH5 -QH 5 -CH2-CH2--CH 2 -CH 2 - -CH,--CH, - OHOH 462462 QH5 QH 5 — CH,- CH,-- CH, - CH, - -OH-OH 463463 -QH5 -QH 5 -CH2-CH,--CH 2 -CH, - -OH-OH 464464 C, H,C, H, -CH,-CH,-CH, -CH, -OH-OH

-C3H7(IiI-C 3 H 7 (II

46(i46 (i - C3H7(IiI- C 3 H 7 (IiI 467467 -C3H7(Ii)-C 3 H 7 (Ii) 46X46X -C3H7(IiI-C 3 H 7 (II 469469 QH5 QH 5 470470 C2H5 C 2 H 5 471471 -('.,H7(IiI- ('., H 7 (IiI 472472 --CjH-(n)--CjH- (n) 473473 C3H7In)C 3 H 7 In) 474474 — C1H-InI- C 1 H-InI 475475 - QH7InI- QH 7 InI 476476 QH5 QH 5 477477 -C,H,(n)-C, H, (n)

C2H5 C 2 H 5

479479 C jC j H,H, 4X04X0 C2 C 2 H,H, 4X14X1 C-C- II,II,

— CH2 — CH2 OH- CH 2 - CH 2 OH

CH2-CH2-OH CH2- CH, OHCH 2 -CH 2 -OH CH 2 - CH, OH

-CH2 -CH, OH CH2-CH2 —OH - CH2 — CH, -O- CH2 — CH2 — OH-CH 2 -CH, OH CH 2 -CH 2 -OH - CH 2 - CH -O- CH 2 - CH 2 - OH

— CH2 — CH, - O — CH, -■ CH2 - OH- CH 2 - CH, - O - CH, - ■ CH 2 - OH

— CH2 - CH, O — CH2 — CH2 — OH -(CH2Ij - (J-(CH2),-- C) C6H,- CH 2 - CH, O - CH 2 - CH 2 - OH - (CH 2 Ij - (J- (CH 2 ), - C) C 6 H,

-C2H5 H-C 2 H 5 H

(CH2), ■- Ο —(CH2U-OH -CH2 -ClI C11H5 (CH 2 ), ■ - Ο - (CH 2 U-OH -CH 2 -ClI C 11 H 5

OHOH

-CH2 -CH C6H,-CH 2 -CH C 6 H,

I OHI OH

— (CH2), O (CH2I2 OCHO (CH2), O (CH2I, O COCH, (CH2), O- (CH2I2 ■■■ O - C11I-I,- (CH 2 ), O (CH 2 I 2 OCHO (CH 2 ), O (CH 2 I, O COCH, (CH 2 ), O- (CH 2 I 2 ■■■ O - C 11 II,

Farbtonhue

HH QH5 QH 5 orangeorange HH QH,QH, orangeorange HH C, H.C, H. orangeorange HH ' H; --' H; OCH, ' H; --'H; OCH, orangeorange CH, — CH2 — QH5 CH, - CH 2 - QH 5 (CH2)., — O — CHlCH3),(CH 2 )., - O - CHlCH 3 ), orangeorange CH, — CH — QH5 CH, - CH - QH 5 CH2-CH2-OHCH 2 -CH 2 -OH orangeorange OHOH C2H5 C 2 H 5 CH2-CH-CH5 CH 2 -CH-CH 5 HH orangeorange OHOH CH, — CH2 — CH2 — OHCH, - CH 2 - CH 2 - OH (CH2)., -O- (CH2), -O- C6H5 (CH 2 )., -O- (CH 2 ), -O- C 6 H 5 CH, - CH, - O — CH, — CH, — OHCH, - CH, - O - CH, - CH, - OH orangeorange CH2-CH-O-CH,CH 2 -CH-O-CH, orangeorange CH,CH, ScharlachScarlet fever ScharlachScarlet fever ScharlachScarlet fever orangeorange orangeorange orangeorange orangeorange gelbyellow orangeorange orangeorange

- CH, — CH2 — O — CH2 - CH2 - OH orange- CH, - CH 2 - O - CH 2 - CH 2 - OH orange

CH, - CH, - OCH,
CH2 CH2-OCH,
CH2 -CH2-OCH,CH, - CH, - OCH,
CH 2 CH 2 -OCH,
CH 2 -CH 2 -OCH,

orange orange orangeorange orange orange

TabelleTabel

CNCN - N- N RR. "-"- NN - · N -=- · N - = NIlNile XX ClCl

CNCN

MlMl

FarbionColor ion

,11,, 11,

ICII2IICII 2 I . ο. ο KK 1H, I4 1 H, I 4 < Ή,<Ή, (Il
I(Il
I. C1 C 1 ,IU, IU OHOH CH2 CH 2 CH,CH, (( Ή;Ή; CII,CII, CH,CH, (( IllIll CH,CH, CII,CII, (( IIIIII

OllOll

0:10: 1

(CII(CII 2 I.I2 I.I - O- O (C(C. Hj)4 OHHj) 4 OH orangeorange K HK H OO (C(C. Hj)4 OHHj) 4 OH orangeorange CH,CH, cncn ( h ( h H,H, orangeorange OHOH IlIl orangeorange IlIl (Mange(Mange IlIl orangeorange 1111th orangeorange (H.(H. (H,(H, (( .H,.H, orangeorange

Fortsetzungcontinuation

4949

5050

Nr.No. RR. C2H5 C 2 H 5 XX — CH2 - OH- CH 2 - OH )j— O — (CHj)4 OH) j - O - (CHj) 4 OH YY -CH-QH5
I -CH-QH 5
I. SS. -CH,— OH-CH, - OH Farbtonhue 490490 -CH2 -CH 2 -CH-QH5 -CH-QH 5 -CH,-CH, OHOH 55 orangeorange — C3H7(n)- C 3 H 7 (n) -CH2-OH-CH 2 -OH OHOH -CH-C6H5
I -CH-C 6 H 5
I. ίί 491491 -CH2 -CH 2 -CH-C6H5 -CH-C 6 H 5 -CH2 -CH 2 OHOH -CHj-OCH3 -CHj-OCH 3 — CHj- CHj- OH- CHj-CHj-OH orangeorange -C3H7In)-C 3 H 7 In) — CH2 — OH- CH 2 - OH OHOH O3-O-(CHj)J-O-QH5 O 3 -O- (CHj) JO-QH 5 -(CHj)3-O-CH(CH3)J- (CHj) 3 -O-CH (CH 3 ) J — CHj - O — CH2 - CHj - OH- CHj - O - CH 2 - CHj - OH 492492 -C3H7In)-C 3 H 7 In) -CH2 -CH 2 -CH2- OH-CH 2 - OH — (CHj)2 — O — (CHj)j — OCHO- (CHj) 2 - O - (CHj) j - OCHO -(CH- (CH -CH-O-QH5 -CH-O-QH 5 -CHj-CHj orangeorange 493493 -CH2 -CH 2 — (CHj)2 O - (CH2I2 — O - COCH3 - (CHj) 2 O - (CH 2 I 2 - O - COCH 3 -CH2 -CH 2 CH3 CH 3 C2H.C 2 H. — CH2 — O — CH2 — CH2 — OH- CH 2 - O - CH 2 - CH 2 - OH orangeorange -C3H7In)-C 3 H 7 In) -CH2-OH-CH 2 -OH - (CHj)3 - O - (CHj)2 - O - QH,- (CHj) 3 - O - (CHj) 2 - O - QH, — Η- Η 494494 -C2H5 -C 2 H 5 -CH2 -CH 2 — CH2 — OH- CH 2 - OH -CH2 -CH 2 — CH2 — OCH3 - CH 2 - OCH 3 ScharlachScarlet fever 495495 -C2H5 -C 2 H 5 -CH2 -CH 2 — CH2 — O — CH2 — CH2 — OH- CH 2 - O - CH 2 - CH 2 - OH -QH.-QH. -CHj-CHj — CH2 — OCH3 - CH 2 - OCH 3 ScharlachScarlet fever 496496 -C3H7 -C 3 H 7 -CH2 -CH 2 — CH2 — O — CH2 — CH2 — OH- CH 2 - O - CH 2 - CH 2 - OH — C6H.- C 6 H. — CHj — OCH3 - CHj - OCH 3 ScharlachScarlet fever 497497 -C3H7 -C 3 H 7 -CH2 -CH 2 — CH2 — O — CH2 — CH2 — OH- CH 2 - O - CH 2 - CH 2 - OH -CH2 -CH 2 -CHj-CHj orangeorange 498498 -C3H7In)-C 3 H 7 In) -CH2 -CH 2 — (CHj)3 — O — (CH2)2 — O — QH5 - (CHj) 3 - O - (CH 2 ) 2 - O - QH 5 orangeorange 499499 - C3H7In)- C 3 H 7 In) -C2H5 -C 2 H 5 -CH2 -CH 2 orangeorange 500500 -C3H7In)-C 3 H 7 In) — Η- Η -CHj-CHj orangeorange 501501 -C2H,-C 2 H, -(CH2 - (CH 2 -CHj-CHj gelbyellow 502502 -C3H7In)-C 3 H 7 In) -CHj-CHj orangeorange 503503 orangeorange - C2H,- C 2 H, -CH2 -CH 2 504504 orangeorange C2H5 C 2 H 5 505505 ' - C2H,'- C 2 H, orangeorange 506506 "C2H,"C 2 H, orangeorange 507507 orangeorange

NH-YNH-Y

Farbtonhue

508508 - 11- 11 509509 C2H,C 2 H, 510510 - CjH,- CjH, 511511 CjH,CjH, 512512 CjH,CjH, 513513 CjH,CjH, 514514 CjH,CjH, 515515 CjH,CjH, 516516 C2H,C 2 H,

C1H7In)C 1 H 7 In)

HH - O- O -(CHj)4-OH- (CHj) 4 -OH HH CHCH -cj-i,-cj-i, HH OHOH (CHj)1 (CHj) 1 CH2 CH 2 CH2 OHCH 2 OH CH2-CH 2 - CH2 CH 2 OHOH CH2 CH 2 OHOH CH2-CH 2 - CH,CH, OHOH CHjCHj (H2 (H 2 CH2 CH 2

CH; CH2 OHCH; CH 2 OH

5IS5IS CC. Λ HΛ H i(n)in) (( H2 H 2 CIIjCIIj OHOH CC. ,11, 11 ,(n), (n) (( H;H; (H;(H; OHOH

(CHj),(CHj), — O- O - (CH2J4 -- (CH 2 J 4 - OHOH (CHj)3 (CHj) 3 — O- O - (CHj)4 -- (CHj) 4 - OHOH CHj-CHj- CHCH - QH5 - QH 5 OHOH HH IlIl IlIl IlIl CH2 CH 2 C1H2 C 1 H 2 CJI,CJI, CH2 CH 2 CH
jCH
j CJI,CJI, OHOH CH2 CH 2 CH
tCH
t CJI,CJI, OHOH ICH2),I 2 ), C)C) (CH2),(CH 2 ), OO < II,<II, CHCH O (Jl,O (Jl,

CJI,CJI,

gelb gelb gelbyellow yellow yellow

gelb gelbyellow yellow

gelb gelb gelb gelbyellow yellow yellow yellow

gelbyellow

gelb gelbyellow yellow

ForlsetzungContinuation

Nr. RNo. R

520520 - C3H7In)- C 3 H 7 In) 521521 C2H5C2H5 522522 -C2H5 -C 2 H 5 523523 — C3H7(n)- C 3 H 7 (n) 524524 - C3H7(Ii)- C 3 H 7 (Ii) 525525 - C3H7(Ii)- C 3 H 7 (Ii) 526526 — C3H7(n)- C 3 H 7 (n) 527527 — C3H,(n)- C 3 H, (n) 528528 -C2H5 -C 2 H 5 529529 -C,H,(n)-C, H, (n)

C2H5 C 2 H 5

-CH2-CH2-OH -CH2-CH,- OH-CH 2 -CH 2 -OH -CH 2 -CH, - OH

— CH2 — CH, — O — CH2 — CH2 — OH- CH 2 - CH, - O - CH 2 - CH 2 - OH

— CH2 — CH2 — O — CH2 — CH2 — OH- CH 2 - CH 2 - O - CH 2 - CH 2 - OH

— CH2 — CH, — O — CH2 - CH, — OH- CH 2 - CH, - O - CH 2 - CH, - OH

»I»I.

-(CH2),- 0-(CH2I4-OH -CH2-CH-QH5 - (CH 2 ), - 0- (CH 2 I 4 -OH -CH 2 -CH-QH 5

OHOH

— CH, -CH-C6H5 - CH, -CH-C 6 H 5

C6H5 C 6 H 5

- C6H5
C6H5 - C 6 H 5
C 6 H 5

-CH2-CH2- OCH,
-(CH2I3-O-CH(CH3),-CH 2 -CH 2 - OCH,
- (CH 2 I 3 -O-CH (CH 3 ),

CH2-CH2-OH
-C2H5
-HCH 2 -CH 2 -OH
-C 2 H 5
-H

- CH, — CH2 — CH2 — OH- CH, - CH 2 - CH 2 - OH

OHOH

531531 -C2H,-C 2 H, COOCH,COOCH, -(CH2), -0-- (CH 2 ), -0- 532532 -C2H5 -C 2 H 5 >—N=^N-
\> —N = ^ N-
\ - (CH,), — 0 -- (CH,), - 0 - 533533 -C2H5 -C 2 H 5 ClCl — (CH2),-O-- (CH 2 ), - O- Tabelle 26Table 26 R CNR CN Cl -^f
VCl - ^ f
V —<C V-NH--Y
>N - <C V-NH-Y
> N NH-XNH-X

ICH2), — OCHO ICH,), —O —COC ICH2),-C)-C6H5 CH, — CH2 — OCH1
CH2-CH2-OCH3
CH, - CH2-OCH3 I 2 ), - OCHO I,), --O --COC I 2 ), - C) -C 6 H 5 CH, - CH 2 - OCH 1
CH 2 -CH 2 -OCH 3
CH, - CH 2 -OCH 3

534534 C2H,C 2 H, — LI- LI iO-(COK- (C H2I4 -H 2 I 4 - -OH-OH 535535 - C2H5 - C 2 H 5 HH - CH —
1 - CH -
1 C6H,C 6 H, 536536 ■■- C2H5 ■■ - C 2 H 5 - H- H OHOH 537537 - C2H5 - C 2 H 5 — H- H CH2 CH 2 OHOH 538538 C2H,C 2 H, IIII -CH,--CH, - CH2 CH 2 - OH- OH 539539 -C2H5 -C 2 H 5 - (CH2I;- (CH 2 I; -CH2 --CH 2 - CH,CH, -OH-OH 540540 - C2H5 - C 2 H 5 - CH2 -- CH 2 - 541541 C2H5 C 2 H 5 -CH2--CH 2 - 542542 -C3H5 -C 3 H 5 -CH2--CH 2 - 543543 C2H,C 2 H, -CH2--CH 2 -

544 --C2H5 544 --C 2 H 5

545 C1IMn)545 C 1 IMn)

546 CjH1InI546 CjH 1 InI

547 C1H-In)547 C 1 H-In)

548 C1IMn)548 C 1 IMn)

544 C6H,544 C 6 H,

550 ( ,IMiH550 (, IMiH

551 CIUn)551 CIUn)

-CH2 CH, OH-CH 2 CH, OH

CW1 CH, OH CW 1 CH, OH

CH, CH, OH CH, CH2 OilCH, CH, OH CH, CH 2 Oil

CH, CII C6II,CH, CII C 6 II,

OHOH

(H, CM, O CH, CIl, CH, Oil(H, CM, O CH, CIl, CH, Oil

IlIl

CW, OH Farbton CW, OH shade

orangeorange

orangeorange

orangeorange

gelbyellow

gelbyellow

gelbyellow

gelbyellow

gelbyellow

gelbyellow

-CH2-CH2-O -CH2-CH2-OH gelb-CH 2 -CH 2 -O -CH 2 -CH 2 -OH yellow

— CH, — CH, -O- CH, CH2 - OH gelb- CH, - CH, -O- CH, CH 2 - OH yellow

gelb gelbyellow yellow

gelbyellow

FarbionColor ion

HH gelbyellow CH3 CH 3 gelbyellow C2H5 C 2 H 5 gelbyellow CH2 — CH2 — OHCH 2 - CH 2 - OH gelbyellow (CH2), - O — (C H2)4 — OH(CH 2 ), - O - (CH 2 ) 4 - OH gelbyellow HH gelbyellow HH gelbyellow HH gelbyellow HH gelbyellow C6H5 C 6 H 5 goldgelb
bis orangegolden yellow
to orange C6H,C 6 H, goldgelb
bis orangegolden yellow
to orange

orangeorange

gelb gelbyellow yellow

OCH3 OCH 3

CH, CH, -C6H5
CW1 CM C6II5 CH, CH, -C 6 H 5
CW 1 CM C 6 II 5

OMOM

CH, CM2 O CH, C 11, OH gelbCH, CM 2 O CH, C 11, OH yellow

CH, CH, OCH3 gelbCH, CH, OCH 3 yellow

ICII1I, O ICH,), O C„IU gell·ICII 1 I, O ICH,), O C "IU gell ·

H gelbH yellow

Fortsetzungcontinuation

5353

5454

l-'arhlonl-'arhlon

552552 -C1H7(Ii)-C 1 H 7 (Ii) -(CH2).,- (CH 2 )., ο -ο - (C(C. H2I, -H 2 I, - OHOH CH,CH, CH2 CH 2 - CH,- CH, OilOil gelbyellow 553553 -C2H5 -C 2 H 5 - H- H CH,CH, CH,CH, -C11H5 -C 11 H 5 gelbyellow 554554 — C3H7(n)- C 3 H 7 (n) -H-H CH2 CH 2 CH2 CH 2 - C11H5 - C 11 H 5 gelbyellow 555555 - C3H7In)- C 3 H 7 In) -H-H CH2 CH 2 CH
iCH
i CJUCJU gelbyellow 556556 - C3H7In)- C 3 H 7 In) -CH,-CH, CH2-CH 2 - C6 C 6 H5 H 5 --•Η- • Η gelbyellow — CH-In! - CH-In! -CH.-CH. CH — ιCH - ι c-1c-1 Λ.Λ. - H- H üelbevil

CH3 CH 3

558 -C3H7In) -CH2-CH-C11H5 558 -C 3 H 7 In) -CH 2 -CH-C 11 H 5

ι CH3 ι CH 3

559 C3H-In) ClI2 -CH, C1,H5 56(1 C3H-In) CH, CH C1, H5 559 C 3 H-In) ClI 2 -CH, C 1 , H 5 56 (1 C 3 H-In) CH, CH C 1 , H 5

OHOH

Tabelle 27Table 27

C (K)CH, R CNC (K) CH, R CN

r- ν νr- ν ν

■- Nil Y■ - Nile Y

■ N
Nil N■ N
Nile N

CH, CH2 OHCH, CH 2 OH

CH2 ( H2 OH
ClI, (H. OHCH 2 (H 2 OH
ClI, (H. OH

gelbyellow

gelbyellow

I arbtonI arbton

561561 C2H5 C 2 H 5 HH O (CO (C H2UH 2 U C)HC) H 562562 C2H5 C 2 H 5 IlIl C\{
I C \ {
I. C6H5 C 6 H 5 563563 C2H5 C 2 H 5 IIII C)HC) H 564564 C2H5 C 2 H 5 HH CH,CH, C)IIC) II 565565 C2H5 C 2 H 5 IlIl CH,CH, CH2 CH 2 - OH- OH 566566 C2H5 C 2 H 5 (CH2I3 (CH 2 I 3 CH2 CH 2 CII2 CII 2 OHOH 567567 C2H5 C 2 H 5 CH,CH, 56X56X C2H5 C 2 H 5 CH2 -CH 2 - 569569 C2H,C 2 H, CH,CH, 57(157 (1 C2H5 C 2 H 5 CH2 CH 2

C2II5 C 2 II 5

C3H7 C 3 H 7

C1H,C 1 H,

576576 ( JU ( JU InIInI 577577 C1H,C 1 H, mimi WKWK C1II-C 1 II- InIInI 571J57 1 y { I 1 1-7{I 1 1-7 5X(I5X (I. C2II,C 2 II, InIInI SKISKI ( Ml-(Ml-

CH, CH2 CH, CH 2

IjHIjH

CH2 CH2 OHCH 2 CH 2 OH

573573 CC. .,H7 ., H 7 CC. 'H2 'H 2 CC. H2 H 2 OHOH 574574 CC. Ml-Ml- CC. Ί1,Ί1, CC. H,H, OHOH

(H, CU C11H,(H, CU C 11 H,

i OHi OH

CH, (H, O C II, CCH, (H, O C II, C

( Π, CH, Oll(Π, CH, Oll

IlIl

1(11,1, O (CH2I4 OH1 (11.1, O (CH 2 I 4 OH

OllOll

CH3
C2H,
CH2-CH2 OHCH 3
C 2 H,
CH 2 -CH 2 OH

(CH2), O (CW2
II(CH 2 ), O (CW 2
II

OCH3 OCH 3

CC. H2 H 2 (TI,(TI, ( „II,("II, CC. H2 H 2 CHCH C11H,C 11 H, OllOll CC. π.-π.- CII,CII, O (O ( CC. H2 H 2 CH;CH; OCH,OCH, (C(C. H2 H 2 I, οI, ο K'H2),K'H 2 ), IlIl CC. H2 H 2 (H,(H, cn.cn. (■(■ H2 H 2 (H,(H, („Π,("Π, CC. H,H, (II.(II. C IlC Il

OHOH

O („IO ("I

OllOll

gelb gclh gelb gelb gelb gelb gelbyellow gclh yellow yellow yellow yellow yellow

gelbyellow

gelbyellow

goldgelb bis orangigolden yellow to orangi

goldgelb bis orangigolden yellow to orangi

orangeorange

gelb i!clbyellow i! clb

gelb gelb gelb gelb uelhyellow yellow yellow yellow uelh

Fortsel/ungFortsel / ung

5656

Ni KNi K

larhtonlarhton

sx: C1Ii-InIsx: C 1 Ii-InI

SKI ( ,H,(nlSKI (, H, (nl

SK4 CMI-InISK4 CMI-InI

SKii C1II-InISKii C 1 II-InI

SK? C1IMnISK? C 1 IMnI

CH, CIl, C11II, CH, CII C11H,CH, CIl, C 11 II, CH, CII C 11 H,

CII1 (H.. CH C11H, CII 1 (H .. CH C 11 H,

CII,CII,

CH, (H.. C11II, (II; CII C1, H, CH, (H .. C 11 II, (II; CII C 1 , H,

OHOH

CH, CH C„H«CH, CH C "H"

CH,
H
HCH,
H
H

CH, CH2 OH CH, CH 2 OH

CU, (H7 Oll CH, CH2 OH CU, (H 7 OII CH, CH 2 OH

gelbyellow

gelb gelbyellow yellow

gelbyellow

gelb gelbyellow yellow

Tabelle 2STable 2S

( H1OC
()(H 1 OC
()

( N(N

R CNR CN

NN- Nil YNN- Nile Y

■ N■ N

NH XNH X

Nr KNo. K

I- arbtonIbton

CII, Cl CII, Cl

OHOH

CH,CH,

C1H-C 1 H-

591591 CH-CH- 592592 CH-CH- 593593 C3H-C 3 H- 594594 -QH--QH- 595595 — CjH7(Ii) - CjH 7 (Ii) 596596 — QH7(n)- QH 7 (n) 597597 — CjH-(n) - CjH- (n) 598598 — QH,(n)- QH, (n) 599599 — QH,(n)- QH, (n) 600600 - QH,(nl- QH, (nl 601601 — QH,(n)- QH, (n) 6Ö26Ö2 — C,H7{n)- C, H 7 (n) 603603 -C3H7(H)-C 3 H 7 (H) 604604 — CjH7(n)- CjH 7 (n) 605605 — H- H 606606 -C3H7(Ii)-C 3 H 7 (Ii)

(H, CIl, OH(H, CIl, OH

CU2 CH, OH CU 2 CH, OH

CHj CHj OH CHj CHj OH

CH, CH, OH CH2 CH2 OHCH, CH, OH CH 2 CH 2 OH

- CHj — CH2 -O- CH2 - CH2 — OH- CHj - CH 2 - O - CH 2 - CH 2 - OH

- CHj — CHj — O - CH2 - CHj — OH- CHj - CHj - O - CH 2 - CHj - OH

- CHj — CH2 — O - CH2 — CH2 - OH -H - CHj - CH 2 - O - CH 2 - CH 2 - OH --H

-H
-H-H
-H

- (CHj)3 - O — (CHjU - OH- (CHj) 3 - O - (CHjU - OH

- CH2 - CH - QH5 - CH 2 - CH - QH 5

OHOH

- CH2 — CH2 — CH2 — OH -CH2-CH2-O-COCH2-O-QH5 - CH 2 - CH 2 - CH 2 - OH -CH 2 -CH 2 -O-COCH 2 -O-QH 5

- (CHj)3 — O — (CH2U — OH -CH2-CH2-O-CH2-Ch2-OCHO- (CHj) 3 - O - (CH 2 U - OH -CH 2 -CH 2 -O-CH 2 -Ch 2 -OCHO

CH, CHCH, CH HH QH,QH, blaustichigrobluish green OHOH HH (H, CH(H, CH HH - QH,- QH, blaustichigrobluish green OHOH HH CH; - CHCH; - CH HH QH5 QH 5 blauslichigrobluishro OHOH HH (CH2I, — O (CH 2 I, - O CH2 — CH2 CH 2 - CH 2 -(CH2I4-- OH- (CH 2 I 4 - OH blaustichigrobluish green Ι(Ή,), ΟΙ (Ή,), Ο - ICH2I2-O- QH,- I 2 I 2 -O- QH, blaustichigrobluish green (CH2I3 — O (CH 2 I 3 - O - CH2 - QH5 - CH 2 - QH 5 blaustichigrobluish green CH2 — CH2 CH 2 - CH 2 — Ο —CHj - Ο - CHj blaustichigrobluish green QH5 QH 5 blaustichigrobluish green C3H7(Ii)C 3 H 7 (Ii) blaustichigrobluish green QH5 QH 5 blaustichigrobluish green (CH2J3 - O(CH 2 J 3 - O -(CH2U-OH- (CH 2 U-OH blaustichigrobluish green CH2 — CHCH 2 - CH -QH5 -QH 5 blaustichigrobluish green OHOH blaustichigrobluish green blaustichigrobluish green blaustichigrobluish green blaustichigrobluish green blaustichigrobluish green blaustichigrobluish green — Ο —CH3 - Ο —CH 3 blaustichigrobluish green

Tabelle 29Table 29

NOj R CNNOj R CN

;· N N ·.. λ Nil Y
(I NH X; · NN · .. λ Nil Y
(I NH X

I arbtonI arbton

CJI,CJI,

CJI7In)CJI 7 In)

610610 C Jl-(HlC Jl- (St. 611611 CJl-InICJl-InI 612612 CJl7In)CJl 7 In) 613613 CJI7In)CJI 7 In) 614614 CJi-InICJi-InI 615615 CJI7 CJI 7 616616 C Jl-C Jl- 617617 C1H7 C 1 H 7 61 S61 p CJl-CJl- 619619 C3H7 C 3 H 7 620620 CJI,CJI, 621621 CJl-,CJl-, 6??6 ?? CJI,CJI, 623623 CJI7 CJI 7 624624 IlIl 625625 CJi7In)CJi 7 in) TabelleTabel 3030th

CH2 CH2 OllCH 2 CH 2 Oll

CH2 CIi2 OHCH 2 Cli 2 OH

CH, CH, OHCH, CH, OH

CH2 CH2 OHCH 2 CH 2 OH

CH2 CH2 OHCH 2 CH 2 OH

CH, CH2-- OHCH, CH 2 - OH

CH2 CHj - O - CH2 CHjCH 2 CHj - O - CH 2 CHj

CHj CH2 O CH2CHjCHj CH 2 O CH 2 CHj

CHj -O - (Hj- CH2 -OHCHj -O - (Hj- CH 2 -OH

CHj
H
H
IlCHj
H
H
Il

(CH2)., O ICH2I4 - OH CU, CH-C1H,(CH 2 )., O ICH 2 I 4 - OH CU, CH-C 1 H,

OHOH

CH2 - CH2 - OHCH 2 - CH 2 - OH

CH2 CIl2 CHj-OH --CH2-CH2-O-COCH2-O-QH, - (CH2I3 — 0 — (CH2I4 — OH -CHj -CH2 Ο — CHj-CH2 OCHOCH 2 CIl 2 CHj-OH --CH 2 -CH 2 -O-COCH 2 -O-QH, - (CH 2 I 3 - 0 - (CH 2 I 4 - OH -CHj -CH 2 Ο - CHj-CH 2 OCHO

(Hj CH
I(Hj CH
I. - H- H C11H5 C 11 H 5 blaustiehigrobluesthigro OHOH — H- H CH2 ClICH 2 ClI HH Cf1H5 Cf 1 H 5 blaustichigrobluish green OHOH — H- H CHj CHCHj CH ΜΜ -QH,-QH, blaustiehigrobluesthigro OHOH JJYY (CHj)3-O(CHj) 3 -O — CH2 - CH2 - CH 2 - CH 2 - (CH2I4 — OH- (CH 2 I 4 - OH blauslichigrobluishro - (CHj)3 O- (CHj) 3 O -(CH2I2-O- QH,- (CH 2 I 2 -O- QH, blaustichigrobluish green - (CHj)3 - O- (CHj) 3 - O -- CHj C6H,- CHj C 6 H, blaustichigrolbluish tinge OHOH — CHj — CH2 - CHj - CH 2 — O — CH,- O - CH, blaustichigrolbluish tinge OHOH -C2H5 -C 2 H 5 blaustichigrolbluish tinge OHOH - C3H1In)- C 3 H 1 In) blaustichigrolbluish tinge — C6H,- C 6 H, blaustichigrolbluish tinge - (CH2I3 -- O- (CH 2 I 3 - O -(CH2I4 OH- (CH 2 I 4 OH blaustichigrotbluish red - CH2-CH- CH 2 -CH - C6H,- C 6 H, blaustichigrotbluish red OHOH blaustichigrotbluish red blaustichigrotbluish red blaustichigrotbluish red blaustichigrotbluish red .H5 .H 5 blaustichigrotbluish red blaustichigrolbluish tinge :ho: ho - O — CH,- O - CH, blaustichigrotbluish red

NO2 R CNNO 2 R CN

O2N-' -\-N--- N—/ V-NH-Y
Br NH XO 2 N- '- \ - N --- N- / V-NH-Y
Br NH X

TITI

-C2H5 -C 2 H 5

— C3H7(n)- C 3 H 7 (n)

629629 -C3H7(n)-C 3 H 7 (n) Β.'ϋΒ.'ϋ — C3H7(Fi)- C 3 H 7 (Fi) 531531 -C3H,(n)-C 3 H, (n) 532532 -C3H7(D)-C 3 H 7 (D) 533533 -C3H7(D)-C 3 H 7 (D)

— CH2 — CH2 — OH -CH2-CH2-OH -CH2-CH2-OH- CH 2 - CH 2 - OH -CH 2 -CH 2 -OH -CH 2 -CH 2 -OH

-CH2-CH2-OH-CH 2 -CH 2 -OH

-CH2-CH2-OH-CH 2 -CH 2 -OH

-CH2-CH2-OH-CH 2 -CH 2 -OH

-CH2-CH2-O-CH2-CHj-OH-CH 2 -CH 2 -O-CH 2 -CHj-OH

-CH2-CH2-O-CH2-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH Farbtonhue

— CH2 — CH — QH5 blaustichigrot- CH 2 - CH - QH 5 bluish-tinted red

OHOH

— CH2 — CH QH5 blaustichigrot- CH 2 - CH QH 5 bluish-tinted red

OHOH

— CH2 — CH — QH5 blaustichigrot- CH 2 - CH - QH 5 bluish-tinted red

OHOH

— (CH2J3 — O - (CH2), — OH hlaustichigrot- (CH 2 J 3 - O - (CH 2 ), - OH bluish red

— (CH2J3 — O — (CH2J2 — O — QH5 blaustichigrot -(CH2J3-O-CH2-QH3 blaustichigrot -CH1-CH2-O-CH3 blaustichigrot- (CH 2 J 3 - O - (CH 2 J 2 - O - QH 5 bluish-tinted red - (CH 2 J 3 -O-CH 2 -QH 3 bluish- tinted red -CH 1 -CH 2 -O-CH 3 bluish-tinted red

— C2H5 blaustichierot- C 2 H 5 bluish red

5959

Farbtonhue

634634 C1H7In)C 1 H 7 In) Br R
\Br R
\ ClI, (II,ClI, (II, ;N ; N O (11, (II, OHO (11, (II, OH C1H7In)C 1 H 7 In) IlIl blaustichigrobluish green 635635 C3H7InIC 3 H 7 InI "S - N N -<"S - N N - < IlIl C11H5 C 11 H 5 IlIl blauslichigrobluishro 636636 C3H7(Ii)C 3 H 7 (Ii) IlIl ((H2)., O ((Hj)4OH((H 2 )., O ((Hj) 4 OH blaustichigrobluish green 637637 C3H7In)C 3 H 7 In) IlIl CHj CH C11H5
jCHj CH C 11 H 5
j ... υ... υ blaustichigrobluish green OHOH - H- H 6M6M (',H7In](', H 7 In] (CH2), O(CH 2 ), O (CHj)4 OH(CHj) 4 OH HH blaustichigrobluish green 639639 C3H7In)C 3 H 7 In) CH2 CHCH 2 CH C11H5 C 11 H 5 — H- H blauslichigrobluishro OHOH — CH2 — CH2 — 0 — CH3 - CH 2 - CH 2 - O - CH 3 640640 C3H7InIC 3 H 7 InI CH2 — CHjCH 2 - CHj OHOH blaustichigrcbluish tint 641641 C1H7(IiIC 1 H 7 (IiI CH2 CH2 CH 2 CH 2 CH2 OHCH 2 OH blauslichigrcblauslichigrc 642642 C3H7In)C 3 H 7 In) CH2CH2 CH 2 CH 2 O- COCH2-O-Q1H5 O- COCH 2 -OQ 1 H 5 blaustichi(ircblaustichi (irc 643643 HH -(CH2I3-O-- (CH 2 I 3 -O- (CHj)4-OH(CHj) 4 -OH blauslichigrcblauslichigrc (>44(> 44 C1H7Ir)C 1 H 7 Ir) CH2 - CH2 -CH 2 - CH 2 - 0-CHj-CH2-OCHO0-CHj-CH 2 -OCHO blaustichigrcbluish tint TabelleTabel 3131 CNCN (J, N -(Y, N - > Nil Y > Nile Y

Farbtonhue

645645 C3H-InIC 3 H-InI 646646 C2H,C 2 H, 647647 C2IUC 2 IU 64 S64 p -CjH5 -CjH 5 64«64 « - C1H-In)- C 1 H-In) 65116511 - C3H7In)- C 3 H 7 In) 651651 — C3H7(n)- C 3 H 7 (n) 652652 — C3H7(n)- C 3 H 7 (n) 653653 - C3H7In)- C 3 H 7 In) TabelleTabel 3232

CHj — CH; — O CH2 — CH2 OH CH2 — CH2 - O - CH2 — CH2 — OH (CHj)3-O-(CHj)4-OH (CHj)2-O-(CHj)2 -OH (CH2)j — O — (CHj)2 — OH (CHj)3-O-(CH2I4-OH (CHj)3-O (CH2I4-OH -(CHj)2-O-(CHi)2-OH HCHj - CH; - O CH 2 - CH 2 OH CH 2 - CH 2 - O - CH 2 - CH 2 - OH (CHj) 3 -O- (CHj) 4 -OH (CHj) 2 -O- (CHj) 2 -OH ( CH 2 ) j - O - (CHj) 2 - OH (CHj) 3 -O- (CH 2 I 4 -OH (CHj) 3 -O (CH 2 I 4 -OH - (CHj) 2 -O- (CHi ) 2 -OH H

— CHj -- CHj -- CHj - CHj - OCH3 OCH 3 violettviolet — C Hj- CHj -- C Hj- CHj - OCH3 OCH 3 violettviolet - CH2 - CH, —- CH 2 - CH, - OCH3 OCH 3 violettviolet -C2H5 -C 2 H 5 violettviolet -C2H5 -C 2 H 5 violettviolet — CH2 — CH2 —- CH 2 - CH 2 - CH2 — OHCH 2 - OH violettviolet — H- H rotviolettred-violet — H- H rotviolettred-violet -(CH2I3-O-- (CH 2 I 3 -O- (CH2), - OH(CH 2 ), - OH rotviolettred-violet

654654 -C2H5 -C 2 H 5 655655 — C3H7(Ii) - C 3 H 7 (Ii) 656656 -C3H7(Ii)-C 3 H 7 (Ii) 657657 — QH7(n) - QH 7 (n) 658658 -C1H7(Ii)-C 1 H 7 (Ii) 659659 -C3H7(D)-C 3 H 7 (D) 660660 -C3H7(H)-C 3 H 7 (H) 661661 -C3H7(Ii)-C 3 H 7 (Ii)

-CH2-CH2-O-CH2-CH2-OH -CH2-CH2-O-CH1-CH2-OH-CH 2 -CH 2 -O-CH 2 -CH 2 -OH -CH 2 -CH 2 -O-CH 1 -CH 2 -OH

- (CH2I3 — O — (CH2U — OH- (CH 2 I 3 - O - (CH 2 U - OH

- (CH2U — O — (CH, I. — OH -(CHj)3-O-(CH2U-OH -(CH2J3-O-(CH2U-OH -CH2-CH2-O-CH2-CH2-OH -H- (CH 2 U - O - (CH, I. - OH - (CHj) 3 -O- (CH 2 U-OH - (CH 2 J 3 -O- (CH 2 U-OH -CH 2 -CH 2 -O-CH 2 -CH 2 -OH -H

Farbtonhue

-CH2-CH2-OCH3 gelbbraun-CH 2 -CH 2 -OCH 3 yellow-brown

-CH2-CH2-OCH3 gelbbraun-CH 2 -CH 2 -OCH 3 yellow-brown

— CH2 — CH2 — OH gelbbraun -CH2-CH2-CH2-OH gelbbraun- CH 2 - CH 2 - OH yellow-brown -CH 2 -CH 2 -CH 2 -OH yellow-brown

-CH2-CH2-O-CH3 gelbbraun-CH 2 -CH 2 -O-CH 3 yellow-brown

— H gelbbraun- H yellow-brown

— H gelbbraun -CH2-CH2-O-CK2-CH2-OH gelbbraun- H yellow-brown -CH 2 -CH 2 -O-CK 2 -CH 2 -OH yellow-brown

6161

la belle 33la belle 33

(N R /(NO /

Ο,Ν '' ■ N N 'χ Ο, Ν '' ■ NN ' χ NIIYNIIY

/ Ν NHX/ Ν NHX

6262

larbtolarbto

WizWiz ( ,M1 (, M 1 (H2(H2 ι(H 2 (H 2 ι !'.MK! '. MK HH (ONH2 (ONH 2 bordobordo W,?W? < Ml-<Ml- (H2(H. ι(H 2 (H. ι !'.,IK! '., IK HH IlIl MolcllMolcll W,4W, 4 (Ml·(Ml (H2(H ((H 2 (H ( „IK"IK HH CONII,CONII, bordobordo OHOH Wi 5Wi 5 (,Hi(,Hi CH2(1H, ιCH 2 ( 1 H, ι : „H.: "H. ( II2( H2OII(II 2 (H 2 OII CONH2 CONH 2 hordohordo W.'.W. '. C1H7 C 1 H 7 (H2(H2 ι(H 2 (H 2 ι !.,IK!., IK CH2CH2OHCH 2 CH 2 OH IlIl vmlfllvmlfll Wi 7Wi 7 (,Ml,(, Ml, CH2CH2OHCH 2 CH 2 OH CH2CH2OHCH 2 CH 2 OH CONH,CONH, hordohordo W*W * <„IK<"IK CH2CH2OHCH 2 CH 2 OH ( H2(H2OH(H 2 (H 2 OH HH \ KiIcIt\ KiIcIt W,')W, ') (Ml,(Ml, CH2CH2OHCH 2 CH 2 OH K HjI1O(CHjI2OHK HjI 1 O (CHjI 2 OH (ONH,(ONH, bordobordo

Claims (4)

Paten tansprüche:Patent claims: 1. Dispersionsa-Ofarbstoffe der 2,6-Diaminopyridinreihe der allgemeinen Formel1. Dispersion dyes of the 2,6-diaminopyridine series the general formula D-N = ND-N = N -NHY-NHY NHXNHX in der D der Rest einer Diazokomponente der Benzol-, Diphenylenoxid-, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe, R Wasserstoff, C2- bis C7-Alkyl oder Phenyl, X und Y Wasserstoff, C,- bis Cg-AlkyJ, durch Hydroxy, C1- bis C8-Alkoxy. Phenoxy, Phenoxyäthoxy, Benzyloxy, Formyloxy, Acetoxy, Chloracetoxy, Äthoxycarbonyloxy, Acetoacetoxy oder Phenoxyacetoxy substituiertes C2- bis C8-Alkyl, Cyclohexyl, Phenyl-C,-bis C4-alkyl. />'-Phenyl~/i-hydroxyäthyl,in which D is the remainder of a diazo component of the benzene, diphenylene oxide, benzthiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series, R is hydrogen, C 2 - to C 7 -alkyl or phenyl, X and Y is hydrogen, C 1 - to Cg -alkyJ, through hydroxy, C 1 - to C 8 -alkoxy. Phenoxy, phenoxyethoxy, benzyloxy, formyloxy, acetoxy, chloroacetoxy, ethoxycarbonyloxy, acetoacetoxy or phenoxyacetoxy substituted C 2 to C 8 alkyl, cyclohexyl, phenyl C 1 to C 4 alkyl. />'- Phenyl ~ / i-hydroxyethyl, -CH-CH2CH-CH-CH 2 CH OHOH gegebenenfalls durch Chlor, Methyl, Methoxy oder Äthoxy substituiertes Phenyl,phenyl optionally substituted by chlorine, methyl, methoxy or ethoxy, (CH2I2O(CH2J2OH(CH 2 I 2 O (CH 2 J 2 OH (CH2I3O(CH2J4OH(CH 2 I 3 O (CH 2 J 4 OH (CH2I3O(CH2J6OH(CH 2 I 3 O (CH 2 J 6 OH (CH2I3OC2H4OCH3
(CH2I3(OC2H4I2OCH3
(CH2I2O(CH2J2OACyI(CH 2 I 3 OC 2 H 4 OCH 3
(CH 2 I 3 (OC 2 H 4 I 2 OCH 3
(CH 2 I 2 O (CH 2 J 2 OACyI (CH2)3O(CH2)4OAcyl
oder(CH 2 ) 3 O (CH 2 ) 4 O acyl
or CH2CH-QH5
OAcylCH 2 CH-QH 5
OAcyl und Z Cyan oder Carbamoyl sind, wobei Acyl CHO, COCH3, COCH2Cl. COCH2COCH,, COCH2OC6H5' COOC2H5, CONHCH, oder CONHC6H5 ist.and Z are cyano or carbamoyl, where acyl is CHO, COCH 3 , COCH 2 Cl. COCH 2 COCH ,, COCH 2 OC 6 H 5 'COOC 2 H 5 , CONHCH, or CONHC 6 H 5 . 2. Farbstoffe gemäß Anspruch I der allgemeinen Formel2. Dyestuffs according to Claim I of the general formula }0} 0 .15.15 A1 A2 A 1 A 2 CNCN N <, ,> NHN <,,> NH .·'·' N
NH X'. · '·' N
NH X ' in der A Nitro, Cyan, Chlor, Brom, Carbomethoxy, ('arboälhoxy, /i-Mcthoxyearbäthoxy, Melhylsulfonyl. Athylsulfonyl, Methyl, Methoxy, Phenylsulfonyl, Phenylazo, A' Wasserstoff, Nitro, Chl· Brom, Cyan, Methyl, Methoxy, Carbometho; Carboäthoxy, Methylsulfonyl, A2 Wasserstc Chlor, Brom, Cyan, Methyl, Methoxy, Nitro, : und Y1 /i-Hydroxyäthyl, -/-Hydroxypropyi od ein Rest der Formelnin which A nitro, cyano, chlorine, bromine, carbomethoxy, ('arboälhoxy, / i-methoxyearbethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy, phenylsulfonyl, phenylazo, A' hydrogen, nitro, chlorine bromine, cyano, methyl, methoxy, Carbomethoxy; Carboethoxy, Methylsulfonyl, A 2 Wasserstc chlorine, bromine, cyano, methyl, methoxy, nitro ,: and Y 1 / i-Hydroxyäthyl, - / - Hydroxypropyi od a remainder of the formulas -(CH2I2 — O -(CH2), — OH — (CH2I3 — O — (CH2J4 — CH -CH2-CH-QH5 -(CH2I6-OH- (CH 2 I 2 - O - (CH 2 ), - OH - (CH 2 I 3 - O - (CH 2 J 4 - CH -CH 2 -CH-QH 5 - (CH 2 I 6 -OH OHOH -CH2-CH2-QH5 -CH2-CH-C6H5 -CH 2 -CH 2 -QH 5 -CH 2 -CH-C 6 H 5 CH3 CH 3 — (CH2I3 — O — (CH2J2 — O — C6H5 -(CH2I3-O-CH2-C6H5 -QH5 - (CH 2 I 3 - O - (CH 2 J 2 - O - C 6 H 5 - (CH 2 I 3 -O-CH 2 -C 6 H 5 -QH 5 -C2H4-O-CH3 -C3H6-OCH3 -C 2 H 4 -O-CH 3 -C 3 H 6 -OCH 3 -CH2-CH2-OCHO — CH2 — CH2 — CH2 — O — CHO-CH 2 -CH 2 -OCHO - CH 2 - CH 2 - CH 2 - O - CHO — CH2 — CH2 — OCOCH3 - CH 2 - CH 2 - OCOCH 3 — CH2 — CH2 — O — CH2 — CH2 — OCHO- CH 2 - CH 2 - O - CH 2 - CH 2 - OCHO — CH2 — CH2 — OCOCH2 — O — C6H,- CH 2 - CH 2 - OCOCH 2 - O - C 6 H, und Wasserstoff und R ein Alkylrest mit 2 bi! 7 Kohlenstoffatomen oder Wasserstoff sind.and hydrogen and R is an alkyl radical with 2 bi! 7 are carbon atoms or hydrogen. 3. Verfahren zur Herstellung von Dispersions azofarbsloffen gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß man die Diazoniumverbindungen von Aminen der allgemeinen Formel 3. A process for the preparation of dispersion azo color fabrics according to claim 1 or 2, characterized characterized in that the diazonium compounds of amines of the general formula D-NH2 D-NH 2 mit Kupplungskomponenten der allgemeinen Formel with coupling components of the general formula /SN'
XHN NHY/ S N '
XHN NHY umsetzt, wobei D, R, X, Y und Z die in Anspruch I oder 2 angegebenen Bedeutungen haben. converts, where D, R, X, Y and Z have the meanings given in claim 1 or 2. 4. Die Verwendung der Farbstoffe gemäß Anspruch 1 oder 2 zum Färben von Textilmaterial aus Acrylnitrilpolymerisaten, synthetischen Polyamiden, Celluloseestern oder Polyestern.4. The use of the dyes according to claim 1 or 2 for dyeing textile material made of acrylonitrile polymers, synthetic polyamides, cellulose esters or polyesters.
DE19722251702 1970-12-19 1972-10-21 Dispersion azo dyes of the 2,6-diamino pyridine series, process for their manufacture and their use Granted DE2251702B2 (en)

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
SU1891749A SU521848A3 (en) 1972-03-10 1973-03-09 The method of obtaining 2,6-diaminopyridine azo dye
IT48707/73A IT979789B (en) 1972-03-10 1973-03-09 AZOCOLORANTS WITH 2, 6 DIAMMINOPYRIDINE DERIVATIVES AS COPULATION COMPONENTS
GB1140873A GB1422650A (en) 1972-03-10 1973-03-09 Azo dyes having 2,6-diaminopyridine derivatives as coupling components
NL7303378A NL7303378A (en) 1972-03-10 1973-03-09
FR7308567A FR2187857B1 (en) 1972-03-10 1973-03-09
JP48027651A JPS6139347B2 (en) 1972-03-10 1973-03-10
CH1472773A CH601427A5 (en) 1972-10-21 1973-10-18
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
DD17417773A DD107067A5 (en) 1972-10-21 1973-10-19
FR7337409A FR2203853B1 (en) 1972-10-21 1973-10-19
JP11800673A JPS4974719A (en) 1972-10-21 1973-10-22
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
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 DE2251702A1 (en) 1974-05-02
DE2251702B2 true DE2251702B2 (en) 1976-11-18

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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)

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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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2640576B2 (en) 1975-10-29 1980-02-07 Bayer Ag, 5090 Leverkusen Use of sulfonic acid group-free azo dyes for dyeing and printing non-tanned cellulose and non-tanned cellulose-containing! Textile material
EP0244740A2 (en) * 1986-05-03 1987-11-11 BASF Aktiengesellschaft Diaminopyridine azo dyes with acyloxy groups

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2640576B2 (en) 1975-10-29 1980-02-07 Bayer Ag, 5090 Leverkusen Use of sulfonic acid group-free azo dyes for dyeing and printing non-tanned cellulose and non-tanned cellulose-containing! Textile material
EP0244740A2 (en) * 1986-05-03 1987-11-11 BASF Aktiengesellschaft Diaminopyridine azo dyes with acyloxy groups
EP0244740A3 (en) * 1986-05-03 1989-04-26 Basf Aktiengesellschaft Diaminopyridine azo dyes with acyloxy groups

Also Published As

Publication number Publication date
GB1438584A (en) 1976-06-09
JPS4974719A (en) 1974-07-18
DD107067A5 (en) 1974-07-12
FR2203853A1 (en) 1974-05-17
FR2203853B1 (en) 1977-08-19
DE2251702A1 (en) 1974-05-02
CH601427A5 (en) 1978-07-14
IT997769B (en) 1975-12-30
CS177151B2 (en) 1977-07-29
BE806349A (en) 1974-04-22

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E77 Valid patent as to the heymanns-index 1977
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