DE1962402A1 - Water-insol monazo dyes for hydrophobic - materials - Google Patents
Water-insol monazo dyes for hydrophobic - materialsInfo
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- DE1962402A1 DE1962402A1 DE19691962402 DE1962402A DE1962402A1 DE 1962402 A1 DE1962402 A1 DE 1962402A1 DE 19691962402 DE19691962402 DE 19691962402 DE 1962402 A DE1962402 A DE 1962402A DE 1962402 A1 DE1962402 A1 DE 1962402A1
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- allyl
- blue
- violet
- methallyl
- ch2ch2cn
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
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Abstract
Description
Wasserunlösliche Monoazofarbstoffe Die vorliegende Erfindung betrifft wertvolle neuewasserunlösliche Monoazofarbstoffe der allgemeinen Formel in der X1 Nitro, Cyan, Alkylsulfonyl oder Dialkylaminosulfonyl, X2 Nitro, Cyan oder ALkylsulfonyl, X3 Cyan, Y Wasserstoff, Alkyl, Alkoxy oder Acylamino, Z Wasserstoff, Alkyl oder Alkoxy, R1 Alkenyl mit 3-19 Kohlenstoffatomen, vorzugsweise 3-4 Kohlenstoffatomen und R2 gegebenenfalls weiter substituiertes Alkyl bedeuten.Water-insoluble monoazo dyes The present invention relates to valuable new water-insoluble monoazo dyes of the general formula in which X1 is nitro, cyano, alkylsulfonyl or dialkylaminosulfonyl, X2 is nitro, cyano or alkylsulfonyl, X3 is cyano, Y is hydrogen, alkyl, alkoxy or acylamino, Z is hydrogen, alkyl or alkoxy, R1 is alkenyl with 3-19 carbon atoms, preferably 3-4 carbon atoms and R2 is optionally further substituted alkyl.
Die neuen Farbstoffe werden auf Ubliche Weise hergestellt durch Kupplung von diazotierten Aminen der allgemeinen Formel mit tertiären Aminen der allgemeinen Formel wobei X1, X2, X3, Y, Z, R1 und R2 die obige Bedeutung haben.The new dyes are prepared in the usual way by coupling diazotized amines of the general formula with tertiary amines of the general formula where X1, X2, X3, Y, Z, R1 and R2 have the above meaning.
Die neuen Azofarbstoffe erhält man ebenfalls, wenn man nach den Lehren des französischen Patents Nr. 1.524.647 die Ealogenatome von Monoazofarbstoffen der allgemeinen Formel in der X1, Y, Z, R1 und R2 die obige Bedeutung haben sowie X2' Chlor, Brom, Nitro, Cyan oder Alkylsulfonyl und X31 Halogen, bevorzugt Chlor oder Brom bedeuten, nucleophil gegen Cyan austauscht.The new azo dyes are also obtained if, according to the teaching of French Patent No. 1,524,647, the ealogen atoms of monoazo dyes of the general formula in which X1, Y, Z, R1 and R2 have the above meanings and X2 'is chlorine, bromine, nitro, cyano or alkylsulfonyl and X31 is halogen, preferably chlorine or bromine, nucleophilically exchanged for cyano.
Zu den neuen Azofaibstoffen gelangt man ferner, wenn man nach den Lehren des französischen Patents Nr. 1.524.647 oder der deutschen Patente ........ (Patentanmeldungen Akeenzeichen P 18 O9 920.2 und P 18 09 921.3) die Halogenatome von Monoazofarbstoffen der allgemeinen Formel in der X1, X3, Y, Z, R1 und R2 die obige Bedeutung hagen und X2" Halogen, bevorzugt Chlor oder Brom bedeutet,nucleophil gegen Cyan, Nitro oder Alkylsulfonyl austaucht.The new azo fibers can also be obtained if the halogen atoms of monoazo dyes are used in accordance with the teachings of French patent No. 1.524.647 or German patents ........ the general formula in which X1, X3, Y, Z, R1 and R2 have the above meaning and X2 "denotes halogen, preferably chlorine or bromine, nucleophilically exchanged for cyano, nitro or alkylsulfonyl.
Die erfindungsgemäßen Farbstoffe zeichnen sich gegenüber den Farbstoffen, die in der tertiären Aminogruppe der Kupplungskomponente anstelle von Alkenylgruppen gesättigte Alkylgruppen enthalten, unter anderem durch eine höhere Ergiebigkeit aus.The dyes according to the invention are distinguished from the dyes those in the tertiary amino group of the coupling component instead of alkenyl groups Contain saturated alkyl groups, among other things due to a higher yield the end.
Als Diazokomponenten,die bei dem vorliegenden Verfahren eingesetzt werden können, seien beispielsweise folgende aufgeführt: 2-Cyan-4,6-dinitranilin, 2,6-Dicyan-4-nitranilin, 2-Cyan-4-nitro-6-alkylsulfonylaniline, 2 ,4-Dicyan-6-nitranilin, 2,4-Dicyan-6-alkylsulfonylaniline, 2,4,6-Tricyananilin, 2-Cyan-4,6-dialkylsulfonylaniline, 2,5-Dicyan-4-alkylsulfonylaniline, 2-Cyan-4-alkylsulfonyl-6-nitraniline, 2-Cyan-4-dialkylaminosulfonyl-6-nitraniline, 2,6-Dicyan-4-dialkylaminosulfonylanilinet 2-Cyan-4-dialkylamino-6-alkylsulfonylaniline.As diazo components used in the present process can be listed, for example, the following: 2-cyano-4,6-dinitraniline, 2,6-dicyan-4-nitro-aniline, 2-cyano-4-nitro-6-alkylsulfonylaniline, 2,4-dicyan-6-nitro-aniline, 2,4-dicyan-6-alkylsulfonylaniline, 2,4,6-tricyananiline, 2-cyano-4,6-dialkylsulfonylaniline, 2,5-dicyano-4-alkylsulfonylaniline, 2-cyano-4-alkylsulfonyl-6-nitroaniline, 2-cyano-4-dialkylaminosulfonyl-6-nitroaniline, 2,6-dicyano-4-dialkylaminosulfonylaniline and 2-cyano-4-dialkylamino-6-alkylsulfonylanilines.
Als Kupplungskomponenten seien beispielsweise aufgeführt: N-Alkyl-N-allylaniline, N-Alkyl-N-methallylaniline, N-Alkyl-N-buten-2-yl-aniline und deren in m-Stellung des Benzolrings substituierten Derivate, wie N-Alkyl-N-allyl-m-toluidine, N-Alkyl-N-methallyl-m-methoxyaniline oder N-Alkyl-N-buten-2-yl-m-acetylaminoaniline; N-Alkyl-N-allyl-2-methyl-5-methoxyaniline N-Alkyl-N-methallyl-2-methyl-5-methoxy-aniline; N-Alkyl-N-(buten-2-yl)-2-methyl-5-methoxy-aniline; N-Alkyl-N-allyl-2-methoxy-5-acetylaminoaniline, N-Alkyl-N-methallyl-2-methoxy-5-acetylaminoaniline; N-Alkyl-N- (buten-2-yl) -2-methoxy-5-acetylaminoaniline; N-Alkyl-N-allyl-2-athoxy-5-acetylaminoaniline; N-Alkyl-N-methallyl-2-äthoxy-5-acetylaminoaniline; N-Alkyl-N-(buten-2-yl)-2-äthoxy-5-acetylaminoaniline.Examples of coupling components are: N-alkyl-N-allylanilines, N-alkyl-N-methallylanilines, N-alkyl-N-buten-2-yl-anilines and their in the m-position of the benzene ring substituted derivatives, such as N-alkyl-N-allyl-m-toluidines, N-alkyl-N-methallyl-m-methoxyanilines or N-alkyl-N-buten-2-yl-m-acetylaminoanilines; N-alkyl-N-allyl-2-methyl-5-methoxyanilines N-alkyl-N-methallyl-2-methyl-5-methoxy-aniline; N-alkyl-N- (buten-2-yl) -2-methyl-5-methoxy-aniline; N-alkyl-N-allyl-2-methoxy-5-acetylaminoanilines, N-alkyl-N-methallyl-2-methoxy-5-acetylaminoanilines; N-alkyl-N- (buten-2-yl) -2-methoxy-5-acetylaminoanilines; N-alkyl-N-allyl-2-ethoxy-5-acetylaminoanilines; N-alkyl-N-methallyl-2-ethoxy-5-acetylaminoanilines; N-alkyl-N- (buten-2-yl) -2-ethoxy-5-acetylaminoanilines.
Alkylgruppen im Sinne vorliegender Erfindung sind bevorzugt Methyl, Äthyl, Butyl, d.h. solche mit 1-4 C-Atomen. Besonders wertvolle Farbstoffe erhält man mit Kupplungskomponenten, deren Alkylgruppe eine ß-substituierte Äthylgruppe, wie Phenäthyl; Hydroxyäthyl; Alkoxyäthyl, wie Äthoxyäthyl; Acyloxyäthyl, wie Acetyloxyäthyl oder Propionyloxyäthyl; Cyanethyl, Alkoxycarbonyläthyl, wie Methoxycarbonyläthyl; Alkylsulfonyläthyl, wie Methylsulfonyläthyl; Nitroäthyl, darstellt.Alkyl groups in the context of the present invention are preferably methyl, Ethyl, butyl, i.e. those with 1-4 carbon atoms. Preserves particularly valuable dyes one with coupling components whose alkyl group is a ß-substituted ethyl group, like phenethyl; Hydroxyethyl; Alkoxyethyl, such as ethoxyethyl; Acyloxyethyl, such as acetyloxyethyl or propionyloxyethyl; Cyanoethyl, alkoxycarbonylethyl, such as methoxycarbonylethyl; Alkylsulfonylethyl, such as methylsulfonylethyl; Nitroethyl.
Mit den neuen Farbstoffen lassen sich synthetische hydrophobe Materialien, wie lineare Polyester, Acetylcellulose, Polyamid und Polycarbonat, in ausgezeichneter Weise färben und bedrucken.With the new dyes, synthetic hydrophobic materials, such as linear polyester, acetyl cellulose, polyamide and polycarbonate, in excellent Color and print wise.
Unter Gebilden aus synthetischen hydrophoben Materialien sind beispielsweise Folien, Filme oder Textilgut, wie Fasern, Fäden, Flocken, Gewebe und Gewirke zu verstehen.Among structures made of synthetic hydrophobic materials are, for example Foils, films or textiles such as fibers, threads, flakes, woven and knitted fabrics to understand.
Textilgut aus Polyestern, wie z.B. PolySthylenglykolterephthalat, oder solchen auf Basis von Terephthalsäure und p-Dimethylolcyclohexan kann man mit den Farbstoffen nach -bekannten Verfahren färben. Die Färbetemperaturen fgr die in wSssriger Dispersion vorliegenden Farbstoffe liegen bei normalem Druck bei 95-100°, vorzugsweise bei 1000 oder unter erhöhtem Druck bei 104-140°. Bei Anwendung von Temperaturen um 100 empfiehlt es sich, dem Färbebad Quellmittel (Carrier) zuzugeben. Als Quellmittel können z.B. aromatische Kohlenwasserstoffe, wie Diphenyl, aromatische Halogenverbindungen, wie Chlorbenzole, aromatische Carbonsäuren, wie Benzoesäure und Salicylsäure, Phenole, wie o- und p-Phenylphenole, Ester, wie Terephthalsäureester, eingesetzt werden. Anstelle des Färbens aus dem Bad kann man auch eine Heißluftfixierung der Farbstoffe bei Temperaturen von 200-2300C vornehmen. Das Bedrucken kann so durchgeführt werden, daß die bedruckte Ware in Gegenwart eines Carriers bei Temperaturen zwischen etwa 80-110° oder in Abwesenheit eines Carriers bei etwa 110-140° gedämpft oder auch nach dem sogenannten Thermofixierverfahren bei etwa 170-230° behandelt wird.Textile goods made from polyesters, such as polythylene glycol terephthalate, or those based on terephthalic acid and p-dimethylolcyclohexane can be used with dye the dyes according to known methods. The dyeing temperatures for the Dyes present in aqueous dispersion are at 95-100 ° under normal pressure, preferably at 1000 or under increased pressure at 104-140 °. at If temperatures around 100 are used, it is advisable to add swelling agents (carriers) to the dye bath. admit. As swelling agents, e.g. aromatic hydrocarbons such as diphenyl, aromatic halogen compounds such as chlorobenzenes, aromatic carboxylic acids such as Benzoic acid and salicylic acid, phenols such as o- and p-phenylphenols, esters such as terephthalic acid esters, can be used. Instead of dyeing from the bath, you can also use hot air fixation Make the dyes at temperatures of 200-2300C. Printing can be carried out in this way be that the printed goods in the presence of a carrier at temperatures between about 80-110 ° or in the absence of a carrier at about 110-140 ° or steamed is also treated according to the so-called thermosetting process at around 170-230 °.
Beispiel 1: In 157 g Nitrosylschwefelsäure (hergestellt aus 150 g Schwefelsäure 660 Be und 7 g Natriumnitrit) werden bei 15020° 20,8 g 2-Cyan-4,6-dinitranilin eingetragen und 3 Stunden bei 200 gerührt.Example 1: In 157 g of nitrosylsulfuric acid (made from 150 g Sulfuric acid 660 Be and 7 g of sodium nitrite) are 20.8 g of 2-cyano-4,6-dinitraniline at 15020 ° entered and stirred at 200 for 3 hours.
21,8 g N-Äthyl-N-allyl-m-acetylaminoanilin werden in der äquivalenten Menge verdünnter wässriger Salzsäure gelöst und mit 1 g Harnstoff, 300 g Eis,sowie mit der vorstehend beschriebenen Diazolösung versetzt. Das Reaktionsgemisch wird mit Eiswasser verdünnt, kurz gerührt, abgesaugt und der Rückstand gründlich mit Wasser gewaschen. Man erhält so nach dem Trocknen ein blaues Farbstoffpulver, das in feindispergierter Form Polyester in einem rotstichig blauen Ton färbt.21.8 g of N-ethyl-N-allyl-m-acetylaminoaniline are in the equivalent Amount of dilute aqueous hydrochloric acid and dissolved with 1 g of urea, 300 g of ice, as well mixed with the above-described diazo solution. The reaction mixture is diluted with ice water, stirred briefly, filtered off with suction and the residue thoroughly with Water washed. This is obtained after drying a blue dye powder, which, in finely dispersed form, dyes polyester in a reddish blue shade.
Beispiel 2: 47,1 g 2-Brom-4-nitro-6-cyab-1-[4'-N-äthyl-N-allylamino-2'-acetylamino-phenylazo]-benzol, 2 g Kupfer-I-oxyd und 10 g Natriumnitrit werden nacheinander in 100 ml Dimethylformamid eingetragen und das Reaktionsgemisch auf 600 erhitzt. Man läßt abkühlen, saugt scharf ab und wäscht den Rückstand mit wenig Dimethylformamid und viel Wasser r,anht Man erhält so 30 g eines blauen Farbstoffpulvers, das mit dem in Beispiel 1 beschriebenen Farbstoff identisch ist.Example 2: 47.1 g of 2-bromo-4-nitro-6-cyab-1- [4'-N-ethyl-N-allylamino-2'-acetylamino-phenylazo] -benzene, 2 g of cuprous oxide and 10 g of sodium nitrite are successively dissolved in 100 ml of dimethylformamide entered and the reaction mixture heated to 600. One lets cool, sucks sharply and the residue was washed with a little dimethylformamide and a lot of water thus receives 30 g of a blue dye powder similar to that described in Example 1 Dye is identical.
Beispiel~3: 47,1 g 2-Brom-4-nitro-6-cyan-1-[4'-N-äthyl-N-allylamino-2'-acetylamino-phenylazo]-benzol, 17 g Zinkmethylsulfinat und 2 g Kupfer-I-oxyd werden nacheinander in 100 ml Dimethylsulfoxyd eingetragen und auf 700 erhitzt Nach einer Stunde Iät man abkühlen, saugt scharf ab und wäscht den Rückstand mit wenig Dimethylsulfoxyd und viel Was nach. Man erhält so 31 g 2-Methylsulfonyl-4-nitro-6-cyan-1-[4'-N-äthyl-N-allylamino-2'-acetylamino-phenylazo]-benzol, das in feindispergierter Form Polyester in einem rotstichig blauen Ton färbt.Example ~ 3: 47.1 g of 2-bromo-4-nitro-6-cyano-1- [4'-N-ethyl-N-allylamino-2'-acetylamino-phenylazo] -benzene, 17 g of zinc methyl sulfinate and 2 g of copper (I) oxide are successively dissolved in 100 ml of dimethyl sulfoxide entered and heated to 700. After an hour, it is allowed to cool, sucked sharply and washes the residue with a little dimethyl sulfoxide and a lot of what. You get so 31 g of 2-methylsulfonyl-4-nitro-6-cyano-1- [4'-N-ethyl-N-allylamino-2'-acetylamino-phenylazo] -benzene, which, in finely dispersed form, dyes polyester in a reddish blue shade.
Beispiel 4: 52,4 g 2-Brom-4-nitro-6-methylsulfonyl-1-[4' '-N-äthyl-N-allylamino-2'-acetylamino-phenylazo]-benzol und 10 g Kupfer-I-cyanid werden in 100 ml Dimethylsulfoxyd eingetragen und auf 1000 erhitzt. Nach 1/4 Stunde läßt man abkühlen, saugt scharf ab und wäscht den Rückstand mit wenig Dimethylsulfoxyd und viel Wasser nach. Man erhält so 36 g eines Farbstoffs, der mit dem in Beispiel 3 beschriebenen identisch ist.Example 4: 52.4 g of 2-bromo-4-nitro-6-methylsulfonyl-1- [4 "-N-ethyl-N-allylamino-2'-acetylamino-phenylazo] -benzene and 10 g of copper (I) cyanide are added to 100 ml of dimethyl sulfoxide and added to 1000 heated. After 1/4 hour the mixture is allowed to cool, sharply suctioned off and the residue is washed with a little dimethyl sulfoxide and a lot of water. This gives 36 g of a dye which is identical to that described in Example 3.
Beispiel 5: 52,5 g 2,6-Dibrom-4-nitro-1-S4l-N-äthyl-N-allylamino-2'-acetylamino-phenylazog-benzol und 20 g Kupfer-l-cyanid werden in 120 ml Dimethylsulfoxyd eingetragen und auf 1000 erhitzt.Example 5: 52.5 g of 2,6-dibromo-4-nitro-1-S4l-N-ethyl-N-allylamino-2'-acetylamino-phenylazog-benzene and 20 g of copper-1-cyanide are added to 120 ml of dimethyl sulfoxide and added to 1000 heated.
Nach 10 Minuten läßt man abkühlen, saugt scharf ab und wäscht den Rückstand mit wenig Dim.ethylsulfoxyd und viel Wasser nach.After 10 minutes it is allowed to cool, sharply suctioned off and washed Add residue with a little Dim.ethylsulfoxyd and a lot of water.
Man erhält so 33 g 2,6-Dicyan-4-nitro-,/"'4'-N-äthyl-N-allylamino-2'-acetylamino-phenylazo]-benzol, das in feindispergierter Form Polyester in einem rotstichig blauen Ton färbt.This gives 33 g of 2,6-dicyan-4-nitro-, / "'4'-N-ethyl-N-allylamino-2'-acetylamino-phenylazo] -benzene, which, in finely dispersed form, dyes polyester in a reddish blue shade.
In der folgenden Tabelle sind weitere erfindungsgemäße Farbstoffe aufgeführt, die Polyesterfasern in den angegebenen Tönen mit ähnlich guten Eigenschaften färben.Further dyes according to the invention are shown in the table below listed, the polyester fibers in the specified shades with similarly good properties to dye.
Allgemeine Formel: Beisp. X1 X2 Y Z R1 R2 Farbton 6 NO2 NO2 H H Allyl CH2CH2CN rotviolett 7 " " H H " CH2CH2OCOCH3 " 8 " " H H Methallyl CH2CH20H violett 9 " II H H Crotenyl CH3 10 " zu CH3 H Allyl CH2CH2CN " 11 " " " H Methallyl CH2CH2COOCH3 " 12 " " C2H5 H Allyl C4H9 " 13 " " " H " CH2CH2OCOC2H5 " 14 " " OCH3 H " CH2CH2-C6H5 rotviolett 15 " " " H Crotenyl C2H5 " 16 " " OC2H5 H Allyl CH2CH2SO2CH3 " 17 " " " H " CH2CH2OH " 18 " " CH3 OCH3 " CH2CH2COOCH3 violett 19 " lt NHCOCH3 H CH3 rotst. blau 20 " " " H " C4H9 " " 21 " " " H Methallyl C2H5 " " 22 " " " H Crotenyl CH3 " " 23 " " " H Allyl CH2CH2OH " " 24 " " " H " CH2CH2OCOCH3 blauviolett 25 " " " H " CH2CH2CN " Beisp. X1 X2 Y Z R1 R2 Farbton 26 N02 NO2 NHCOCH3 H Allyl CH2CH2-C6H5 violett 27 " " " H " CH2CH2SO2C2H5 " 28 " " NHCOC2H5 H " CH2CH2COOCH3 rotst blau 29 " " NHCOC3H7 H " CH2CH2NO2 blauviolet 30 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 31 " " NHCONH2 H Methallyl C2H5 rotst.General formula: Example X1 X2 YZ R1 R2 shade 6 NO2 NO2 HH allyl CH2CH2CN red-violet 7 "" HH "CH2CH2OCOCH3" 8 "" HH methallyl CH2CH20H violet 9 "II HH crotenyl CH3 10" to CH3 H allyl CH2CH2CN "11""" H methallyl CH2COlCN "11""""12""C2H5 H allyl C4H9" 13 """H" CH2CH2OCOC2H5 "14""OCH3H" CH2CH2-C6H5 red-violet 15 """H crotenyl C2H5" 16 "" OC2H5 H allyl CH2CH2SO2CH3 "17""" H. ""18""CH3OCH3" CH2CH2COOCH3 violet 19 "lt NHCOCH3 H CH3 red. blue 20 """H" C4H9 "" 21 """H Methallyl C2H5""22""" H Crotenyl CH3 "" 23 """H Allyl CH2CH2OH""24""" H "CH2CH2OCOCH3 blue violet 25""" H "CH2CH2CN" ex. X1 X2 YZ R1 R2 color 26 N02 NO2 NHCOCH3 H allyl CH2CH2-C6H5 violet 27 """H" CH2CH2SO2C2H5 "28""NHCOC2H5H" CH2CH2COOCH3 "redst blue 29""NHCOC3Hiolet H2 H "CH2CH2OCOOCH3" 31 "" NHCONH2 H Methallyl C2H5 rotst.
blau 32 " " NHCONHC2H5 H Allyl CH2CH20COCH3 blauviolett 33 " " NHCONHC3H5 H " CH3 rotst. blue 32 "" NHCONHC2H5 H allyl CH2CH20COCH3 blue-violet 33 "" NHCONHC3H5 H "CH3 rotst.
blau 34 " " NHCOCH2Cl H " C2H5 " 35 " " NHCOCH2OH H " " " 36 " " NHCOCH2OCH3 H " " " 37 " " NHCOCH2OCOCH3 H " " " 38 " " NHCOCH2CN H " " " 39 " " NHCOCH3 CH3 Crotenyl C4H9 grünst. blue 34 "" NHCOCH2Cl H "C2H5" 35 "" NHCOCH2OH H "" "36" " NHCOCH2OCH3 H "" "37" "NHCOCH2OCOCH3 H" "" 38 "" NHCOCH2CN H "" "39" " NHCOCH3 CH3 Crotenyl C4H9 green.
blau 40 " ' " " lt C2H5 Allyl CH2CH20H lt 41 " " " OCH3 " C2H5 " 42 " " " " " CH2CH2CN blau 43 " " " " Methallyl CH2CH2OCOCH3 " Beisp. X1 X2 Y Z R1 R2 Farbton 44 NO2 NO2 NHCOCH3 OC2H5 Allyl CH2CH2OH grünst.bla 45 " " " " " CH2CH2OCOCH3 blau 46 " " lt II II CH2CH2COOCH3 grünst. blue 40 "'" "lt C2H5 Allyl CH2CH20H lt 41" "" OCH3 "C2H5" 42 "" "" "CH2CH2CN blue 43" "" "Methallyl CH2CH2OCOCH3" Ex. X1 X2 Y Z R1 R2 Color 44 NO2 NO2 NHCOCH3 OC2H5 Allyl CH2CH2OH green, blue 45 " "" "" CH2CH2OCOCH3 blue 46 "" lt II II CH2CH2COOCH3 green.
blau 47 " " " " " CH2CH2CN blau 48 " " " " " C4H9 grünst.blau 49 " " NHCOC2H5 " " CH3 " " 50 " " NHCOOCH3 " " C2H5 " " 51 " " NHCONHC2H5 " " " " " 52 " " NHCOCH3 OC2H4OH " " " " 53 " " " OC2H4OCOCH3 " " " " 54 " " " OC2H4Cl " " " " 55 " " " OC2H4CN " " " " 56 " CN H H " CH2CH2CN rotviolet 57 " " H H " CH2CH2OCOCH3 " 58 " " H H Methallyl CH2CH2OH violett 59 " " H H Crotenyl CH3 II 60 " " CH3 H Allyl CH2CH2CN 61 " " " H Methallyl CH2CH2COOCH3 62 II II C2H5 H Allyl C4H9 II 63 " " " H " CH2CH2OCOC2H5 " Beisp. X1 X2 Y Z R1 R2 Farbton rot-64 NO2 CN OCH3 H Allyl CH2CH2-C6H5 violet 65 lt lt II H Crotenyl C2H5 " 66 " " OC2H5 H Allyl CH2CH2SO2CH3 " 67 " " " H " CH2CH2OH " 68 " " CH3 OCH3 " CH2CH2COOCH3 violet 69 " " NHCOCH3 H " CH3 rotst. blue 47 "" "" "CH2CH2CN blue 48" "" "" C4H9 green blue 49 "" NHCOC2H5 "" CH3 "" 50 "" NHCOOCH3 "" C2H5 "" 51 "" NHCONHC2H5 "" "" "52" "NHCOCH3 OC2H4OH" "" "53" "" OC2H4OCOCH3 "" "" 54 "" "OC2H4Cl" "" "55" "" OC2H4CN "" "" 56 "CN H H" CH2CH2CN red-violet 57 "" H H "CH2CH2OCOCH3 "58" "H H Methallyl CH2CH2OH violet 59" "H H Crotenyl CH3 II 60" "CH3 H Allyl CH2CH2CN 61 "" "H Methallyl CH2CH2COOCH3 62 II II C2H5 H Allyl C4H9 II 63 "" "H" CH2CH2OCOC2H5 " Example X1 X2 Y Z R1 R2 color red-64 NO2 CN OCH3 H Allyl CH2CH2-C6H5 violet 65 lt lt II H Crotenyl C2H5 "66" "OC2H5 H allyl CH2CH2SO2CH3 "67" "" H "CH2CH2OH" 68 "" CH3 OCH3 "CH2CH2COOCH3 purple 69 "" NHCOCH3 H "CH3 rotst.
bl.au 70 " " " H " C4H9 " 71 " " " H Methallyl C2H5 " 72 " " " H Crotenyl CH3 " 73 " " " H Allyl CH2CH2OH " 74 " " " H " CH2CH2OCOCH3 blau violett 75 " " " H " CH2CH2CN " 76 " " " H " CH2CH2-C6H5 " 77 " " " H " CH2CH2SO2C2H5 " 78 " " NHCOC2H5 H " CH2CH2COOCH3 rotst. bl.au 70 "" "H" C4H9 "71" "" H Methallyl C2H5 "72" "" H Crotenyl CH3 "73" "" H Allyl CH2CH2OH "74" "" H "CH2CH2OCOCH3 blue violet 75 "" "H" CH2CH2CN "76" "" H "CH2CH2-C6H5" 77 "" "H" CH2CH2SO2C2H5 " 78 "" NHCOC2H5 H "CH2CH2COOCH3 rotst.
blau 79 " " NHCOC3H7 H " CH2CH2NO2 blauviolet 80 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 81 " " NHCONH H Methallyl C2H5 rotst. blue 79 "" NHCOC3H7 H "CH2CH2NO2 blue violet 80" "NHCOOCH3 H" CH2CH2OCOOCH3 "81" "NHCONH H Methallyl C2H5 rotst.
blau 82 lt lt NHCONHC2H5 H Allyl CH2CH2OCOCH blauviolett Beisp. X1 X2 Y Z R1 R2 Farbton 83 NO2 CN NHCONHC3H5 H Allyl CH3 rotst.blau 84 " " NHCOCH2Cl H " C2H5 " " 85 " " NHCOCH2 H " " " " 86 " " NHCOCH2OCH3 H " " " " 87 " " NHCOCH2OCOCH3 H " " " " 88 " " NHCOCH2CN H " " " " 89 " " NHCOCH3 CH3 Crotenyl C4H9 grünst.blau 90 " " " C2H5 Allyl CH2CH2OH " " 91 " " " OCH3 " C2H5 " " 92 " " " " " CH2CH2CN blau 93 " " " " Methallyl CH2CH2OCOCH3 " 94 " " " OC2H5 Allyl CH2CH2OH grünst.blau 95 " " " " " CH2CH2OCOCH3 blau 96 " " " " " CH2CH2COOCH3 grünst. blue 82 lt lt NHCONHC2H5 H Allyl CH2CH2OCOCH blue-violet Ex. X1 X2 Y Z R1 R2 Color 83 NO2 CN NHCONHC3H5 H Allyl CH3 reddish blue 84 "" NHCOCH2Cl H "C2H5" "85" "NHCOCH2 H" "" "86" "NHCOCH2OCH3 H" "" "87" "NHCOCH2OCOCH3 H "" "" 88 "" NHCOCH2CN H "" "" 89 "" NHCOCH3 CH3 Crotenyl C4H9 green-blue 90 "" "C2H5 Allyl CH2CH2OH" "91" "" OCH3 "C2H5" "92" "" "" "CH2CH2CN blue 93 "" "" methallyl CH2CH2OCOCH3 "94" "" OC2H5 allyl CH2CH2OH green-blue 95 "" "" "CH2CH2OCOCH3 blue 96" "" "" CH2CH2COOCH3 green.
blau 97 " " " " " CH2CH2CN blau 98 " " " " " C4H9 grünst.blau 99 " " NHCOC2H5 " " CH3 " " 100 " " NHCOOCH3 " " C2H5 " " 101 " " NHCONHC2H5 " " " " " Beisp. X1 X2 Y Z R1 R2 Farbton 102 N02 CN NHCOCH3 OC2H40H Allyl C2H5 grünst.blau 103 " " " OC2H4OCOCH3 " " " " 104 " " " OC2H4Cl " " " " 105 " " " OC2H4CN " " " " 106 " SO2CH3 H H " CH2CH2CN rot-bzw. violett SO2C2H5 107 " " H H " CH2CH2OCOCH3 " 108 " " H H Methallyl CH2CH2OH violett 109 " " H H Crotenyl CH3 " 110 " " CH3 H Allyl CH2CH2CN " 111 " " " " Methallyl CH2CH2COOCH3 " 112 " " C2H5 " Allyl C4H9 " 113 " " " " " CH2CH2OCOC2H5" 114 " " OCH3 H " CH2CH2-C6H5 ro violett 115 " " " H Crotenyl C2H5 " 116 " " OC2H5 H Allyl CH2CH2SO2CH3 " 117 " " " H " CH2CH2OH " 118 " " CH3 OCH3 " CH2CH2COOCH3 violett 119 " " NHCOCH3 H " CH3 rots blau 120 " " " H " C4H9 " Beisp. X1 X2 Y Z R1 R2 Farbton 121 NO2 SO2CH3 NHCOCH3 H Methallyl C2H5 rotst. blue 97 "" "" "CH2CH2CN blue 98" "" "" C4H9 green blue 99 "" NHCOC2H5 "" CH3 "" 100 "" NHCOOCH3 "" C2H5 "" 101 "" NHCONHC2H5 "" " "" Ex. X1 X2 Y Z R1 R2 shade 102 N02 CN NHCOCH3 OC2H40H Allyl C2H5 green blue 103 "" "OC2H4OCOCH3" "" "104" "" OC2H4Cl "" "" 105 "" "OC2H4CN" "" "106" SO2CH3 H H "CH2CH2CN red or violet SO2C2H5 107" "H H "CH2CH2OCOCH3" 108 "" H H Methallyl CH2CH2OH purple 109 "" H H Crotenyl CH3 "110" "CH3 H Allyl CH2CH2CN" 111 "" "" Methallyl CH2CH2COOCH3 "112" "C2H5 "Allyl C4H9" 113 "" "" "" CH2CH2OCOC2H5 "114" "OCH3 H" CH2CH2-C6H5 red purple 115 "" "H Crotenyl C2H5" 116 "" OC2H5 H Allyl CH2CH2SO2CH3 "117" "" H "CH2CH2OH "118" "CH3 OCH3" CH2CH2COOCH3 violet 119 "" NHCOCH3 H "CH3 red blue 120 "" "H" C4H9 " Example X1 X2 Y Z R1 R2 Color 121 NO2 SO2CH3 NHCOCH3 H Methallyl C2H5 rotst.
bzw. blau S02C2H5 122 " " " H Crotenyl CH3 " 123 " " " H Allyl CH2CH20H " 124 " " " H " CH2CH2OCOCH3 blau violett 125 " " " H " CH2CH2CN 126 " " " H " CH2CH2-C6H5 127 " " " H " CH2CH2SO2C2H5 128 " " NHCOC2H5 H " CH2CH2COOCH3 rotst. or blue S02C2H5 122 "" "H crotenyl CH3" 123 "" "H allyl CH2CH20H "124" "" H "CH2CH2OCOCH3 blue violet 125" "" H "CH2CH2CN 126" "" H "CH2CH2-C6H5 127 "" "H" CH2CH2SO2C2H5 128 "" NHCOC2H5 H "CH2CH2COOCH3 rotst.
blau 129 " " NHCOC3H7 H " CH2CH2N02 blauviolett 130 " " NHCOOCH3 H " CH2CH2OCOOCH3 131 " " NHCONH2 H Methallyl C2H5 rotst. blue 129 "" NHCOC3H7 H "CH2CH2N02 blue-violet 130" "NHCOOCH3 H "CH2CH2OCOOCH3 131" "NHCONH2 H Methallyl C2H5 rotst.
blau 132 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 blau violett 133 " " NHCONHC3H5 H " CH3 rotst blau 134 " " NHCOCH2Cl H " C2H5 135 " " NHCOCH2OH H " " " 136 " " NHCOCH2OCH3 H " " " 137 " " NHCOCH2OCOCH3 H " " " 138 " " NHCOCH2CN H " " " Beisp. X1 X2 Y Z R1 R2 Farbton 139 NO2 S°2CH3 NHCOCH3 CH3 Crotenyl C4H9 grünst. blue 132 "" NHCONHC2H5 H allyl CH2CH2OCOCH3 blue violet 133 "" NHCONHC3H5 H "CH3 redst blue 134" "NHCOCH2Cl H" C2H5 135 "" NHCOCH2OH H "" "136" "NHCOCH2OCH3 H" "" 137 "" NHCOCH2OCOCH3 H "" "138" "NHCOCH2CN H "" " Example X1 X2 Y Z R1 R2 color 139 NO2 S ° 2CH3 NHCOCH3 CH3 Crotenyl C4H9 green.
bzw. blau SO2C2H5 140 " " " C2H5 Allyl CH2CH2OH " 141 " " " OCH3 " C2H5 " 142 " " " " " CH2CH2CN blau 143 " " " " Methallyl CH2CH2OCOCH3 " 144 " " " OC2H5 Allyl CH2CH2OH grünst. or blue SO2C2H5 140 "" "C2H5 allyl CH2CH2OH" 141 "" "OCH3 "C2H5" 142 "" "" "CH2CH2CN blue 143" "" "Methallyl CH2CH2OCOCH3" 144 " "" OC2H5 allyl CH2CH2OH green.
blau 145 " " " " " CH2CH2OCOCH3 blau 146 " " " " " CH2CH2COOCH3 grüns blau 147 " " " " " CH2CH2CN blau 148 " " " " " C4H9 grünst. blue 145 "" "" "CH2CH2OCOCH3 blue 146" "" "" CH2CH2COOCH3 green blue 147 "" "" "CH2CH2CN blue 148" "" "" C4H9 green.
blau 149 " " NHCOC2H5 " " CH3 " 150 " " NHCOOCH3 " " C2H5 " 151 " " NHCONHC2H5 " " " " 152 " " NHCOCH3 OC2H4OH " " " 153 " " " OC2H4OCOCH3" " " 154 " " " OC2H4Cl " " " 155 " " " OC2H4CN " " " Beisp. X1 X2 Y Z R1 R2 Farbton 156 CN N02 H H Allyl CH2CH2CN bordo 157 " " H H " CH2CH2OCOCH3 " 158 " " H H Methallyl CH2CH20H rotviolett 159 " " H H Crotenyl CH3 " 160 " " CH3 H Allyl CH2CH2CN " 161 " " " H Methallyl CH2CH2COOCH3 " 162 " " C2H5 H Allyl C4H9 " 163 " " " H " CH2CH2OCOC2H5 " 164 " " OCH3 H " CH2CH2-C6H5 bordo 165 " " " H Crotenyl C2H5 " 166 " " OC2H5 H Allyl CH2CH2SO2CH3 " 167 " " " H " CH2CH2OH " 168 " " CH3 OCH3 " CH2CH2COOCH3 rotviolet 169 " " NHCOCH3 H " CH3 blauviolett 170 " " " H " C4H9 " 171 " " " H Methallyl C2H5 " 172 " " " H Crotenyl CH3 " 173 " " " H Allyl CH2CH2OH " 174 " " " H " CH2CH2OCOCH3 violet 175 " " " H " CH2CH2CN " Beisp. X1 X2 Y Z R1 R2 Farbton 176 CN NO2 NHCOCH3 H Allyl CH2CH2-C6H5 violett 177 " " " H " CH2CH2SO2C2H5 " 178 " " NHCOC2H5 H " CH2CH2COOCH3 blauviolet 179 " " NHCOC3H7 " CH2CH2NO2 violett 180 " " NHCOOCH3 " CH2CH2OCOOCH3 " 181 " " NHCONH2 H Methallyl C2H5 blauviolet 182 " NHCONHC2H5 H Allyl CH2CH20COCH3 violett 183 " " NHCONHC3H5 H " CH3 blauviolett 184 " " NHCOCH2Cl H " C2H5 " 185 " " NHCOCH2OH H " " " 186 " " NHCOCH2OCH3 H " " " 187 " " NHCOCH2OCOCH3 H " " " 188 " " NHCOCH2CN H " " " 189 " " NHCOCH3 CH3 Crotenyl C4H9 bla 190 " " " C2H5 Allyl CH2CH2OH " 191 " " It OCH3 " C2H lt 192 " " " " " CH2CH2CN 193 " " " " Methallyl CH2CH2OCOCH3 Beisp. X1 X2 Y Z R1 R2 Farbton 194 CN NO2 NHCOCH3 OC2H5 Allyl CH2CH20H blau 195 " " " " " CH2CH2OCOCH3 " 196 " " " " " CH2CH2COOCH3 " 197 " " " " " CH2CH2CN 198 " " " " " C4H9 " 199 " " NHCOC2H5 " " CH3 " 200 " " NHCOOCH3 " " C2H5 " 201 " " NHCONHC2H5 " " " " 202 " " NHCOCH3 OC2H4OH " " " 203 " " " OC2H4OCOCH3 " " " 204 " " " OC2H4Cl " " " " 205 " " " OC2H4CN " " " 206 " CN H H " CH2CH2CN bordo 207 " " H H " CH2CH2OCOCH3 " 208 " " H H Methallyl CH2CH2OH rotviolett 209 " " H H Crotenyl CH3 " 210 " " CH3 H Allyl CH2CH2CN " 211 " " " H Methallyl CH2CH2COOCH3 " 212 " " C2H5 H Allyl C4H II 213 " " " H " CH2CH2OCOC2H Beisp. X1 X2 Y Z R1 R2 Farbton 214 CN CN OCH3 H Allyl CH2CH2-C6H5 bordo 215 " " " H Crotenyl C2H5 " 216 " " OC2H5 H Allyl CH2CH2SO2CH3 " 217 " " " H " CH2CH2OH " 218 " " CH3 OCH3 " CH2CH2COOCH3 rotviolett 219 " " NHCOCH3 H " CH3 blau violett 220 " " " H " C4H9 " 221 " " " H Methallyl C2H5 " 222 " " " H Crotenyl CH3 " 223 " " " H Allyl CH2CH2OH " 224 " " " H " CH2CH2OCOCH3 violet 225 " " " H " CH2CH2CN " 226 " " " H " CH2CH2-C6H5 " 227 " " " H " CH2CH2SO2C2H5 " 228 " " NHCOC2H5 H " CH2CH2COOCH3 blauviolett 229 " " NHCOC3H7 H " CH2CH2NO2 violet 230 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 231 " " NHCONH3 H Methallyl C3H5 blauviolett 232 " " NHCONHC2H5 H Allyl CH2CH20COCH3 violett Beisp. X1 X2 Y Z R1 R2 Farbton 233 CN CN NHCONHC3H5 H Allyl CH3 blauviolett 234 " " NHCOCH2Cl H " C2H5 " 235 " " NHCOCH2OH H " " " 236 " " NHCOCH2OCH3 H " " " 237 " " NHCOCH2OCOCH3 H " " " 238 " " NHCOCH2CN H " " " 239 " " NHCOCH3 CH3 Crotenyl C4H9 blau 240 " " " C2H5 Allyl CH2CH2OH " 241 " " " OCH3 " C2H5 " 242 " " " " " CH2CH2CN " 243 " " " " Methallyl CH2CH2OCOCH3 " 244 " " " OC2H5 Allyl CH2CH2OH " 245 " " " " " CH2CH2OCOCH3 " 246 " " " " " CH2CH2COOCH3 " 247 " " " " " CH2CH2CN " 248 " " " " " C4H9 " 249 " " NHCOC2H5 " " CH3 " 250 " " NHCOOCH3 " " C2H5 " 251 " " NHCONHC2H5 " " " " 252 " " NHCOCH3 OC2H4OH " " " Beisp. X1 X2 Y Z R1 R2 Farbton 253 CN CN NHCOCH3 OC2H4OCOCH3 Allyl C2H5 blau 254 " " " OC2H4Cl " " " 255 " " " OC2H4CN " " " 256 " SO2CH3 H H " CH2CH2CN bordo bzw. blue 149 "" NHCOC2H5 "" CH3 "150" "NHCOOCH3" "C2H5" 151 " "NHCONHC2H5" "" "152" "NHCOCH3 OC2H4OH" "" 153 "" "OC2H4OCOCH3" "" 154 "" "OC2H4Cl" "" 155 "" "OC2H4CN" "" Example X1 X2 Y Z R1 R2 shade 156 CN N02 H H allyl CH2CH2CN bordo 157 "" H H "CH2CH2OCOCH3" 158 "" H H Methallyl CH2CH20H red-violet 159 "" H H Crotenyl CH3 "160" "CH3 H Allyl CH2CH2CN "161" "" H Methallyl CH2CH2COOCH3 "162" "C2H5 H Allyl C4H9" 163 "" "H" CH2CH2OCOC2H5 "164" "OCH3 H" CH2CH2-C6H5 bordo 165 "" "H Crotenyl C2H5 "166" "OC2H5 H allyl CH2CH2SO2CH3" 167 "" "H" CH2CH2OH "168" "CH3 OCH3 "CH2CH2COOCH3 red-violet 169" "NHCOCH3 H" CH3 blue-violet 170 "" "H" C4H9 "171" "" H Methallyl C2H5 "172" "" H Crotenyl CH3 "173" "" H Allyl CH2CH2OH "174" "" H "CH2CH2OCOCH3 violet 175" "" H "CH2CH2CN" Ex. X1 X2 Y Z R1 R2 Color 176 CN NO2 NHCOCH3 H Allyl CH2CH2-C6H5 violet 177 "" " H "CH2CH2SO2C2H5" 178 "" NHCOC2H5 H "CH2CH2COOCH3 blue violet 179" "NHCOC3H7 "CH2CH2NO2 violet 180" "NHCOOCH3" CH2CH2OCOOCH3 "181" "NHCONH2 H methallyl C2H5 blue purple 182 "NHCONHC2H5 H allyl CH2CH20COCH3 purple 183" "NHCONHC3H5 H "CH3 blue violet 184" "NHCOCH2Cl H" C2H5 "185" "NHCOCH2OH H" "" 186 " "NHCOCH2OCH3 H" "" 187 "" NHCOCH2OCOCH3 H "" "188" "NHCOCH2CN H" "" 189 "" NHCOCH3 CH3 Crotenyl C4H9 bla 190 "" "C2H5 Allyl CH2CH2OH" 191 "" It OCH3 "C2H lt 192" "" "" CH2CH2CN 193 "" "" "Methallyl CH2CH2OCOCH3 Ex. X1 X2 Y Z R1 R2 Color 194 CN NO2 NHCOCH3 OC2H5 Allyl CH2CH20H blue 195 "" "" "CH2CH2OCOCH3" 196 "" "" "" CH2CH2COOCH3 "197" "" "" "CH2CH2CN 198" "" " "C4H9" 199 "" NHCOC2H5 "" CH3 "200" "NHCOOCH3" "C2H5" 201 "" NHCONHC2H5 "" "" 202 "" NHCOCH3 OC2H4OH "" "203" "" OC2H4OCOCH3 "" "204" "" OC2H4Cl "" "" 205 "" "OC2H4CN" "" 206 "CN H H" CH2CH2CN bordo 207 "" H H "CH2CH2OCOCH3 "208" "H H Methallyl CH2CH2OH red-violet 209" "H H Crotenyl CH3" 210 "" CH3 H allyl CH2CH2CN "211" "" H methallyl CH2CH2COOCH3 "212" "C2H5 H allyl C4H II 213 "" "H" CH2CH2OCOC2H Example X1 X2 Y Z R1 R2 color shade 214 CN CN OCH3 H allyl CH2CH2-C6H5 bordo 215 "" "H crotenyl C2H5" 216 "" OC2H5 H Allyl CH2CH2SO2CH3 "217" "" H "CH2CH2OH" 218 "" CH3 OCH3 "CH2CH2COOCH3 red-violet 219 "" NHCOCH3 H "CH3 blue violet 220" "" H "C4H9" 221 "" "H Methallyl C2H5 "222" "" H crotenyl CH3 "223" "" H allyl CH2CH2OH "224" "" H "CH2CH2OCOCH3 violet 225 "" "H" CH2CH2CN "226" "" H "CH2CH2-C6H5" 227 "" "H" CH2CH2SO2C2H5 "228" "NHCOC2H5 H" CH2CH2COOCH3 blue violet 229 "" NHCOC3H7 H "CH2CH2NO2 violet 230 "" NHCOOCH3 H "CH2CH2OCOOCH3" 231 "" NHCONH3 H methallyl C3H5 blue-violet 232 "" NHCONHC2H5 H allyl CH2CH20COCH3 purple Example X1 X2 Y Z R1 R2 shade 233 CN CN NHCONHC3H5 H allyl CH3 blue-violet 234 "" NHCOCH2Cl H "C2H5" 235 "" NHCOCH2OH H "" "236" "NHCOCH2OCH3 H" "" 237 "" NHCOCH2OCOCH3 H "" "238" "NHCOCH2CN H" "" 239 "" NHCOCH3 CH3 Crotenyl C4H9 blue 240 "" "C2H5 Allyl CH2CH2OH" 241 "" "OCH3" C2H5 "242" "" "" "CH2CH2CN" 243 "" "" Methallyl CH2CH2OCOCH3 "244" "" OC2H5 Allyl CH2CH2OH "245" "" "" "CH2CH2OCOCH3 "246" "" "" CH2CH2COOCH3 "247" "" "" "CH2CH2CN" 248 "" "" "" C4H9 "249 "" NHCOC2H5 "" CH3 "250" "NHCOOCH3" "C2H5" 251 "" NHCONHC2H5 "" "" 252 "" NHCOCH3 OC2H4OH "" " Example X1 X2 Y Z R1 R2 color 253 CN CN NHCOCH3 OC2H4OCOCH3 Allyl C2H5 blue 254 "" "OC2H4Cl" "" 255 "" "" OC2H4CN "" "256" SO2CH3 H H "CH2CH2CN bordo resp.
S02C2H5 257 " " H H " CH2CH2OCOCH3 258 " " H H Methallyl CH2CH2OH rotviolett 259 " " H H Crotenyl CH3 " 260 " " CH3 H Allyl CH2CH2CN " 261 " lt " H Methallyl CH2CH2COOCH3 " 262 " " C2H5 H Allyl C4H9 " 263 " " " H " CH2CH2OCOC2H5" 264 " " OCH3 H " CH2CH2-C6H5 bord 265 " " " H Crotenyl C2H5 " 266 " " OC2H5 H Allyl CH2CH2SO2CH3 " 267 " " " H " CH2CH2OH " 268 " " CH3 OCH3 " CH2CH2COOCH3 rotviolett 269 " " NHCOCH3 H " CH3 blau violett 270 " " " H " C4H9 " Beisp. X1 X2 Y Z R1 R2 Farbton 271 CN S°2CH3 NHCOCH3 H Methallyl C2H5 blauviolett bzw. S02C2H5 257 "" H H "CH2CH2OCOCH3 258" "H H Methallyl CH2CH2OH red-violet 259 "" H H Crotenyl CH3 "260" "CH3 H Allyl CH2CH2CN" 261 "lt" H Methallyl CH2CH2COOCH3 "262" "C2H5 H Allyl C4H9" 263 "" "H" CH2CH2OCOC2H5 " 264 "" OCH3 H "CH2CH2-C6H5 bord 265" "" H Crotenyl C2H5 "266" "OC2H5 H Allyl CH2CH2SO2CH3 "267" "" H "CH2CH2OH" 268 "" CH3 OCH3 "CH2CH2COOCH3 red-violet 269 "" NHCOCH3 H "CH3 blue violet 270" "" H "C4H9" Ex. X1 X2 Y Z R1 R2 Color 271 CN S ° 2CH3 NHCOCH3 H Methallyl C2H5 blue-violet or
S02C2H5 272 " " " H Crotenyl CH3 " 273 " " " H Allyl CH2CH2OH " 274 " " " H " CH2CH2OCOCH3 violett 275 " " " H " CH2CH2CN 276 " " " H " CH2CH2-C6H5 " 277 " " " H " CH2CH2SO2C2H5 " 278 " " NHCOC2H5 " CH2CH2COOCH3 " 279 " " NHCOC3H7 H " CH2CH2NO2 " 280 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 281 " " NHCONH2 H Methallyl C 2H5 blauviolett 282 " " NHCONHC 2H5 H Allyl CH2CH2OCOCH3 violett 283 " " NHCONHC3H5 H " CH3 blauviolet 284 " " NHCOCH2Cl H " C2H5 " 285 " " NHCOCH2OH H " " " 286 " " NHCOCH2OCH3 H " " " 287 " " NHCOCH2OCOCH3 H " " " 288 " " NHCOCH2CN H " " " Beisp. X1 X2 Y Z R1 R2 Farbton 289 CN SO2CH3 NHCOCH3 CH3 Crotenyl C4H9 blau bzw. S02C2H5 272 "" "H Crotenyl CH3" 273 "" "H Allyl CH2CH2OH" 274 "" "H" CH2CH2OCOCH3 violet 275 "" "H" CH2CH2CN 276 "" "H" CH2CH2-C6H5 "277" "" H "CH2CH2SO2C2H5" 278 "" NHCOC2H5 "CH2CH2COOCH3" 279 "" NHCOC3H7 H "CH2CH2NO2" 280 "" NHCOOCH3 H "CH2CH2OCOOCH3" 281 "" NHCONH2 H methallyl C 2H5 blue violet 282 "" NHCONHC 2H5 H allyl CH2CH2OCOCH3 violet 283 "" NHCONHC3H5 H "CH3 blue violet 284" "NHCOCH2Cl H" C2H5 "285" "NHCOCH2OH H" "" 286 " "NHCOCH2OCH3 H" "" 287 "" NHCOCH2OCOCH3 H "" "288" "NHCOCH2CN H" "" Ex. X1 X2 Y Z R1 R2 color 289 CN SO2CH3 NHCOCH3 CH3 Crotenyl C4H9 blue resp.
SO2C2H5 290 " " " C2H5 Allyl CH2CH2OH " 291 " " " OCH3 " C2H5 " 292 " " " " " CH2CH2CN " 293 " " " " Methallyl CH2CH2OCOCH3 " 294 " " " OC2H5 Allyl CH2CH2OH " 295 " " " " " CH2CH2OCOCH3 " 296 " " " " " CH2CH2COOCH3 " 297 " " " " " CH2CH2CN " 298 " " " " " C4H9 " 299 " " NHCOC2H5 " " CH3 " 300 " " NHCOOCH3 " " C2H5 " 301 " " NHCONHC2H5 " " " " 302 " " NHCOCH3 OC2H4OH " " " 303 " " " OC2H4OCOCH3" " " 304 " " " OC2H4Cl " " " 305 " " " OC2H4CN " " " 306 SO2CH3 NO2 H H " CH2CH2CN rot bzw. SO2C2H5 290 "" "C2H5 allyl CH2CH2OH" 291 "" "OCH3" C2H5 "292 "" "" "CH2CH2CN" 293 "" "" Methallyl CH2CH2OCOCH3 "294" "" OC2H5 Allyl CH2CH2OH "295" "" "" CH2CH2OCOCH3 "296" "" "" "CH2CH2COOCH3" 297 "" "" "CH2CH2CN" 298 "" "" "C4H9" 299 "" NHCOC2H5 "" CH3 "300" "NHCOOCH3" "C2H5" 301 "" NHCONHC2H5 "" "" 302 "" NHCOCH3 OC2H4OH "" "303" "" OC2H4OCOCH3 "" "" 304 "" "OC2H4Cl" "" 305 "" "OC2H4CN" "" 306 SO2CH3 NO2 H H "CH2CH2CN red or
SO2C2H5 307 " " H H " CH2CH2OCOCH3 " Beisp. X1 X2 Y Z R1 R2 Farbton 308 S02CH3 NO2 H H Methallyl CH2CH2OH bordo bzw. SO2C2H5 307 "" H H "CH2CH2OCOCH3" Example X1 X2 Y Z R1 R2 shade 308 S02CH3 NO2 H H methallyl CH2CH2OH bordo or
S02C2H5 309 " II H H Crotenyl CH3 310 " II CH3 H Allyl CH2CH2CN " 311 " " " H Methallyl CH2CH2COOCH3 " 312 " " C2H5 H Allyl C4H9 " 313 " " " H " CH2CH2OCOC2H5" 314 " " OCH3 H " CH2CH2-C6H5 " 315 " " " H Crotenyl C2H5 " 316 " " OC2H5 H Allyl CH2CH2SO2CH3 " 317 " " " H " CH2CH2OH 318 " " CH3 PCH3 " CH2CH2COOCH3 rotviolett 319 " " NHCOCH3 H " CH3 blauviolet 320 " " " H " C4H9 " 321 " " " H Methallyl C2H5 " 322 " " " H Crotenyl CH3 " 323 " " " H Allyl CH2CH2OH " 324 " " " H " CH2CH2OCOCH3 rotviolett 325 " " " H " CH2CH2CN 326 " " " H " CH2CH2-C6H5 Beisp. X1 X2 Y Z R1 R2 Farbton 327 SO2CH3 NO2 NHCOCH3 H Allyl CH2CH2SO2C2H5 rot bzw. violett S02C2H5 328 " " NHCOC2H5 H " CH2CH2COOCH3 " 329 " " NHCOC3H7 H " CH2CH2NO2 " 330 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 331 " " NHCONH2 H Methallyl C2H5 violett 332 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 rotviolett 333 " " NHCONHC3H5 H " CH3 violett 334 " " NHCOCH2Cl H " C2H5 " 335 " " NHCOCH2OH H " " " 336 " " NHCOCH2OCH3 H " " " 337 " " NHCOCH2OCOCH3 H " " " 338 " " NHCOCH2CN H " " " 339 " " NHCOCH3 CH3 Crotenyl C4H9 blau 340 " " " C2H5 Allyl CH2CH2OH " 341 " " " OCH3 " C2H5 " 342 " " " " " CH2CH2CN " 343 " " " " " Methallyl CH2CH2OCOCH3 " 344 " " " OC2H5 Allyl CH2CH2OH " 345 " " " " " CH2CH2OCOCH3 " Beisp. X1 X2 Y Z R1 R2 Farbton 346 SO2CH3 N02 NHCOCH3 OC2H5 Allyl CH2CH2COOCH3 blau bzw. S02C2H5 309 "II H H Crotenyl CH3 310" II CH3 H Allyl CH2CH2CN " 311 "" "H Methallyl CH2CH2COOCH3" 312 "" C2H5 H Allyl C4H9 "313" "" H "CH2CH2OCOC2H5" 314 "" OCH3 H "CH2CH2-C6H5" 315 "" "H Crotenyl C2H5" 316 "" OC2H5 H Allyl CH2CH2SO2CH3 "317" "" H "CH2CH2OH 318" "CH3 PCH3" CH2CH2COOCH3 red-violet 319 "" NHCOCH3 H "CH3 blue violet 320" "" H "C4H9" 321 "" "H Methallyl C2H5 "322" "" H Crotenyl CH3 "323" "" H Allyl CH2CH2OH "324" "" H "CH2CH2OCOCH3 red purple 325 "" "H" CH2CH2CN 326 "" "H" CH2CH2-C6H5 Ex. X1 X2 Y Z R1 R2 Color 327 SO2CH3 NO2 NHCOCH3 H Allyl CH2CH2SO2C2H5 red or violet S02C2H5 328 "" NHCOC2H5 H "CH2CH2COOCH3" 329 "" NHCOC3H7 H "CH2CH2NO2" 330 "" NHCOOCH3 H "CH2CH2OCOOCH3" 331 "" NHCONH2 H Methallyl C2H5 violet 332 " "NHCONHC2H5 H allyl CH2CH2OCOCH3 red-violet 333" "NHCONHC3H5 H" CH3 violet 334 "" NHCOCH2Cl H "C2H5" 335 "" NHCOCH2OH H "" "336" "NHCOCH2OCH3 H" " "337" "NHCOCH2OCOCH3 H" "" 338 "" NHCOCH2CN H "" "339" "NHCOCH3 CH3 Crotenyl C4H9 blue 340 "" "C2H5 allyl CH2CH2OH" 341 "" "OCH3" C2H5 "342" "" "" CH2CH2CN "343" "" "" "Methallyl CH2CH2OCOCH3" 344 "" "OC2H5 Allyl CH2CH2OH "345" "" "" CH2CH2OCOCH3 " Example X1 X2 Y Z R1 R2 color shade 346 SO2CH3 N02 NHCOCH3 OC2H5 Allyl CH2CH2COOCH3 blue resp.
S02C2H5 347 " " " " " CH2CH2CN " 348 " " " " " C4H9 " 349 " " NHCOC2H5 " " CH3 " 350 " " NHCOOCH3 " " C2H5 " 351 " " NHCONHC2H5 " " " " 352 " " NHCOCH3 OC2H4OH " " " 353 " " " OC2H4OCOCH3" " " 354 " " " OC2H4Cl " " " 355 " " " OC2H4CN " " " 356 " CN H H " CH2CH2CN rot 357 " " H H " CH2CH2OCOCH3 " 358 " " H H Methallyl CH2CH2OH bordo 359 " " H H Crotenyl CH3 " 360 " " CH3 H Allyl CH2CH2CN " 361 " " " H Methallyl CH2CH2COOCH3 " 362 " " C2H5 H Allyl C4H9 " 363 " " " H " CH2CH2OCOC2H5 " 364 " " OC 3 H " CH2CH2-C6H5 " Beisp. X1 X2 Y Z R1 R2 Farbton 365 S02CH3 CN OCH3 H Crotenyl C2H5 bordo bzw. S02C2H5 347 "" "" "CH2CH2CN" 348 "" "" "" C4H9 "349" "NHCOC2H5 "" CH3 "350" "NHCOOCH3" "C2H5" 351 "" NHCONHC2H5 "" "" 352 "" NHCOCH3 OC2H4OH "" "353" "" OC2H4OCOCH3 "" "354" "" OC2H4Cl "" "355" "" OC2H4CN "" "356" CN H H "CH2CH2CN red 357" "H H" CH2CH2OCOCH3 "358" "H H Methallyl CH2CH2OH bordo 359 "" H H Crotenyl CH3 "360" "CH3 H Allyl CH2CH2CN" 361 "" "H Methallyl CH2CH2COOCH3" 362 "" C2H5 H Allyl C4H9 "363" "" H "CH2CH2OCOC2H5 "364" "OC 3 H" CH2CH2-C6H5 " Example X1 X2 Y Z R1 R2 color tone 365 S02CH3 CN OCH3 H Crotenyl C2H5 bordo or
S02C2H5 366 " " OC2H5 H Allyl CH2CH2SO2CH3 " 367 " " " H " CH2CH2OH " 368 " " CH3 OCH3 " CH2CH2COOCH3 rotviolett 369 " " NHCOCH3 H " CH3 blau violett 370 " " " H " C4H9 " 371 " " " H Methallyl C2H5 " 372 " " " H Crotenyl CH3 " 373 " " " H Allyl CH2CH2OH " 374 " " " H " CH2CH2OCOCH3 rotviolett 375 " " " H " CH2CH2CN " 376 " " " H " CH2CH2-C6H5 " 377 " " " H " CH2CH2SO2C2H5 " 378 " " NHCOC2H5 H " CH2CH2COOCH3 " 379 " " NHCOC3H7 H " CH2CH2NO2 " 380 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 381 lt " NHCONH2 H Methallyl C2H5 violett 382 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 rotviolett Beisp. X1 X2 Y æ R1 R2 Farbton 383 S02CH3 CN NHCONHC3H5 H Allyl CH3 violett bzw. S02C2H5 366 "" OC2H5 H allyl CH2CH2SO2CH3 "367" "" H "CH2CH2OH "368" "CH3 OCH3" CH2CH2COOCH3 red-violet 369 "" NHCOCH3 H "CH3 blue violet 370 "" "H" C4H9 "371" "" H Methallyl C2H5 "372" "" H Crotenyl CH3 "373 "" "H Allyl CH2CH2OH" 374 "" "H" CH2CH2OCOCH3 red-violet 375 "" "H" CH2CH2CN "376" "" H "CH2CH2-C6H5" 377 "" "H" CH2CH2SO2C2H5 "378" "NHCOC2H5 H" CH2CH2COOCH3 "379" "NHCOC3H7 H" CH2CH2NO2 "380" "NHCOOCH3 H" CH2CH2OCOOCH3 "381 lt" NHCONH2 H methallyl C2H5 violet 382 "" NHCONHC2H5 H allyl CH2CH2OCOCH3 red-violet Example X1 X2 Y æ R1 R2 color 383 S02CH3 CN NHCONHC3H5 H Allyl CH3 violet or
S02C2H5 384 " " NHCOCH2C1 H C 2H5 385 " " NHCOCH2OH H " " " 386 " " NHCOCH2OCH3 H " " " 387 " " NHCOCH2OCOCH3 H " " " 388 " " NHCOCH2CN H " " " 389 " " NHCOCH3 CH3 Crotenyl C4H9 bla 390 " " " C2H5 Allyl CH2CH2OH " 391 " " " OCH3 " C2H5 " 392 " " " " " CH2CH2CN " 393 " " " " Methallyl CH2CH2OCOCH3" 394 " " " OC2H5 Allyl CH2CH2OH " 395 " " " " " CH2CH2OCOCH3" 396 " " " " " CH2CH2COOCH3" 397 " " " " " CH2CH2CN " 398 " " " " " C4H9 " 399 " " NHCOC2H5 " " CH3 " 400 " " NHCOOCH3 " " C2H5 " 401 " " NHCONHC2H5 " " " " Beisp. X1 X2 Y Z R1 R2 Farbton 402 S°2CH3 CN NHCOCH3 OC2H4OH Allyl C 2H5 blau bzw. S02C2H5 384 "" NHCOCH2C1 H C 2H5 385 "" NHCOCH2OH H "" "386" "NHCOCH2OCH3 H" "" 387 "" NHCOCH2OCOCH3 H "" "388" "NHCOCH2CN H" "" 389 "" NHCOCH3 CH3 crotenyl C4H9 bla 390 "" "C2H5 allyl CH2CH2OH" 391 "" "OCH3 "C2H5" 392 "" "" "CH2CH2CN" 393 "" "" Methallyl CH2CH2OCOCH3 "394" "" OC2H5 allyl CH2CH2OH "395" "" "" "CH2CH2OCOCH3" 396 "" "" "CH2CH2COOCH3" 397 "" "" "CH2CH2CN" 398 "" "" "" C4H9 "399" "NHCOC2H5" "CH3" 400 "" NHCOOCH3 "" C2H5 "401" "NHCONHC2H5" "" " Example X1 X2 Y Z R1 R2 color tone 402 S ° 2CH3 CN NHCOCH3 OC2H4OH Allyl C 2H5 blue resp.
S02C2H5 403 " " " OC2H4OCOCH3 " " " 404 " " " OC2H4Cl " " " 405 " " " OC2H4CN " " " 406 " SO2CH3 H H " CH2CH2CN ro bzw. S02C2H5 403 "" "OC2H4OCOCH3" "" 404 "" "OC2H4Cl" "" 405 " "" OC2H4CN "" "406" SO2CH3 H H "CH2CH2CN ro or
SO2C2H5 407 " " H H " CH2CH2OCOCH3" 408 " " H H Methallyl CH2CH20H bordo 409 " " H H Crotenyl CH3 " 410 " " CH3 H Allyl CH2CH2CN " 411 " " " H Methallyl CH2CH2COOCH3" 412 " " C2H5 H Allyl C4H9 " 413 " " " H " CH2CH2OCOC2H5" 414 " " OCH3 H " CH2CH2-C6H5 " 415 " " " H Crotenyl C2H5 " 416 " " OC2H5 H Allyl CH2CH2SO2CH3" 417 " " " H " CH2CH2OH " 418 " " CH3 OCH3 " CH2CH2COOCH3 rotviolett Beisp. X1 X2 Y Z R1 R2 Farbton 419 SO2CH3 SO2CH3 NHCOCH3 H Allyl CH3 blauviolet bzw. bzw. SO2C2H5 407 "" H H "CH2CH2OCOCH3" 408 "" H H Methallyl CH2CH20H bordo 409 "" H H crotenyl CH3 "410" "CH3 H allyl CH2CH2CN" 411 "" "H methallyl CH2CH2COOCH3 "412" "C2H5 H allyl C4H9" 413 "" "H" CH2CH2OCOC2H5 "414" "OCH3 H "CH2CH2-C6H5" 415 "" "H Crotenyl C2H5" 416 "" OC2H5 H Allyl CH2CH2SO2CH3 " 417 "" "H" CH2CH2OH "418" "CH3 OCH3" CH2CH2COOCH3 red-violet Ex. X1 X2 Y Z R1 R2 Color 419 SO2CH3 SO2CH3 NHCOCH3 H Allyl CH3 blue-violet or resp.
SO2C2H5 SO2C2H5 420 " " " H " C4H9 " 421 " " " H Methallyl C2@5 " 422 " " " H Crotenyl CH3 " 423 " " " H Allyl CH2CH2OH " 424 " " " H " CH2CH2OCOCH3 rotviolett 425 " " " H " CH2CH2CN " 426 " " " H " CH2CH2-C6H5 " 427 " " " H " CH2CH2SO2C2H5 " 428 " " NHCOC2H5 H " CH2CH2COOCH3 " 429 " " NHCOC3H7 H " CH2CH2NO2 " 430 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 431 " " NHCONH2 H Methallyl C2H5 violett 432 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 rotviolett 433 " " NHCONHC3H5 H " CH3 violett 434 " " NHCOCH2Cl H " C2H5 " 435 " " NHCOCH2OH H " " " 436 " " NHCOCH2OCH3 H " " " Beisp. X1 X2 Y Z R1 R2 Farbton 437 SO2CH3 SO2CH3 NHCOCH20COCH3 H Allyl C2H5 violett bzw. bzw. SO2C2H5 SO2C2H5 420 "" "H" C4H9 "421" "" H Methallyl C2 @ 5 " 422 "" "H Crotenyl CH3" 423 "" "H Allyl CH2CH2OH" 424 "" "H" CH2CH2OCOCH3 red violet 425 "" "H" CH2CH2CN "426" "" H "CH2CH2-C6H5" 427 "" "H" CH2CH2SO2C2H5 "428" "NHCOC2H5 H" CH2CH2COOCH3 "429" "NHCOC3H7 H" CH2CH2NO2 "430" "NHCOOCH3 H "CH2CH2OCOOCH3" 431 "" NHCONH2 H Methallyl C2H5 violet 432 "" NHCONHC2H5 H allyl CH2CH2OCOCH3 red-violet 433 "" NHCONHC3H5 H "CH3 violet 434" "NHCOCH2Cl H "C2H5" 435 "" NHCOCH2OH H "" "436" "NHCOCH2OCH3 H" "" Ex. X1 X2 Y Z R1 R2 Color 437 SO2CH3 SO2CH3 NHCOCH20COCH3 H Allyl C2H5 violet or respectively.
SO2C2H5 SO2C2H5 438 " " NHCOCH2CN H " " " 439 " " NHCOCH3 CH3 Crotenyl C4H9 bla 440 " " " C2H5 Allyl CH2CH2OH " 441 " " " OCH3 " C2H5 " 442 " " " " " CH2CH2CN " 443 " " " " Methallyl CH2CH2OCOCH3 " 444 " " " OC2H5 Allyl CH2CH2OH " 445 " " " " " CH2CH2OCOCH3" 446 " " " " " CH2CH2COOCH3" 447 " " " " " CH2CH2CN " 448 " " " " " C4H9 " 449 " " NHCOC2H5 " " CH3 " 450 " " NHCOOCH3 " " C2H5 " 451 " " NHCONHC2H5 " " " " 452 " " NHCOCH3 OC2H4OH " " " 453 " " " OC2H4OCOCH3" " " 454 " " " OC2H4Cl " " " 455 " " " OC2H4CN " " " Beisp. X1 X2 Y Z R1 R2 Farbton 456 SO2N(CH3) NO2 H H Allyl CH2CH2CN rot 457 " " H H " CH2CH2OCOCH3 " 458 ' " H H Methallyl CH2CH2OH bordo 459 " " H H Crotenyl CH3 " 460 " CH3 H Allyl CH2CH2CN lt 461 " " " H Methallyl CH2CH2COOCH3 " 462 " " C2H5 H Allyl C4H9 " 463 " " " H " CH2CH2OCOC2H5" 464 " " OCH3 H " CH2CH2-C6H5 " 465 " " lt II H Crotenyl C 2H5 466 " " OC2H5 H Allyl CH2CH2SO2CH3 467 " " " H " CH2CH2OH 468 CH3 OCH3 CH2CH2COOCH rotviolett 469 " " NHCOCH3 H " CH3 blauviolett 470 " " " H " C4H9 471 " " " H Methallyl C2H5 472 " " " H Crotenyl CH3 473 " " " H Allyl CH2CH2OH Beisp. X1 X2 Y Z R1 R2 Farbton 474 SO2N(CH3)2 NO2 NHCOCH3 H Allyl CH2CH2OCOCH3 rotviolett 475 " " " H " CH2CH2CN " 476 " " " H " CH2CH2-C6H5 " 477 " " " H " CH2CH2SO2C2H5 " 478 " " NHCOC2H5 H " CH2CH2COOCH3 " 479 " " NHCOC3H7 H " CH2CH2NO2 " 480 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 481 " " NHCONH2 H Methallyl C 2H5 violett 482 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 rot violett 483 lt " NHCONHC3H5 H " CH3 violett 484 " " NHCOCH2Cl H " C2H5 " 485 " " NHCOCH2OH H " " " 486 " " NHCOCH2OCH3 H " " " 487 " " NHCOCH2OCOCH3 H " " " 488 " " NHCOCH2CN H " " " 489 " " NHCOCH3 CH3 Crotenyl C4H9 blau 490 " lt C2H5 Allyl CH2CH2OH lt 491 " " " OCH3 " C2H5 " 492 " " " " " CH2CH2CN " 493 " " " " Methallyl CH2CH2OCOCH3" Beisp. X1 X2 Y Z R1 R2 Farbton 494 S02N(CH3)2 N02 NHCOCH3 OC2H5 Allyl CH2CH2OH blau 495 " " " " " CH2CH2OCOCH3 " 496 " " " " " CH2CH2COOCH3 " 497 " " " " " CH2CH2CN " 498 " " " " " C4H9 " 499 " " NHCOC2H5 " " CH3 " 500 " " NHCOOCH3 " " C2H5 " 501 lt lt NHCONHC2H5 " " " 502 " NHCOCH3 OC2H40H lt II 503 " " " OC2H4OCOCH3 " " " 504 " " OC2H4Cl " " " 505 " " " OC2H4CN " " " 506 " CN H H " CH2CH2CN rot 507 " " H H " CH2CH2OCOCH3 " 508 " " H H Methallyl CH2CH2OH bord 509 " " H H Crotenyl CH3 " 510 " " CH3 H Allyl CH2CH2CN " 511 " " " H Methallyl CH2CH2COOCH3" 512 " " C2H5 H Allyl C4H9 " 513 " " " H " CH2CH2OCOC2H5 " Beisp. X1 X2 Y Z R1 R2 Farbton 514 SO2N(CH3)2 CN OCH3 H Allyl CH2CH2-C6H5 bord 515 " " " H Crotenyl C2H5 " 516 " " OC2H5 H Allyl CH2CH2SO2CH3 " 517 " " " H " CH2CH2OH " 518 " " CH3 OCH3 " CH2CH2COOCH3 rot violett 519 " " NHCOCH3 H " CH3 blauviolett 520 " " " H " C4H9 " 521 " " " H Methallyl C2H5 " 522 " " " H Crotenyl CH3 " 523 " " " H Allyl CH2CH2OH " 524 " " " H " CH2CH2OCOCH3 rotviolett 525 " " " H " CH2CH2CN " 526 " " " H " CH2CH2-C6H5 " 527 " " " H " CH2CH2SO2C2H5 " 528 " " NHCOC2H5 H " CH2CH2COOCH3 " 529 " " NHCOC3H7 H " CH2CH2NO2 " 530 " " NHCOOCH3 H " CH2CH2OCOOCH3 " 531 " " NHCONH2 H Methallyl C2H5 violett 532 " " NHCONHC2H5 H Allyl CH2CH2OCOCH3 rotviolett Beisp. X1 X2 Y Z R1 R2 Farbton 533 SO2N(CH3)2 CN NHCONHC3H5 H Allyl CH3 violett 534 " " NHCOCH2Cl H " C2H5 " 535 " " NHCOCH2OH H " " " 536 " " NHCOCH2OCH3 H " " " 537 " " NHCOCH2OCOCH3 H " " " 538 " " NHCOCH2CN H " " " 539 " " NHCOCH3 CH3 Crotenyl C4H9 blau 540 " " " C2H5 Allyl CH2CH2OH " 541 " " " OCH3 " C2H5 " 542 " " " " " CH2CH2CN " 543 " " " " Methallyl CH2CH2OCOCH3" 544 " " " OC2H5 Allyl CH2CH2OH " 545 " " " " " CH2CH2OCOCH3" 546 " " " " " CH2CH2COOCH3 " 547 " " " " " CH2CH2CN " 548 " " " " " C4H9 " 549 " " NHCOC2H5 " " CH3 " 550 " " NHCOOCH3 " " C2H5 " 551 " " NHCONHC2H5 " " " " Beisp. X1 X2 Y Z R1 R2 Farbton 552 SO2N(CH3)2 CN NHCOCH3 OC2H4OH Allyl C2H5 blau 553 " " " OC2H4OCOCH3 " " " 554 " " " OC2H4Cl " " " 555 " " " OC2H4CN " " " Beispiel 556: In eine Färbeflotte, deren pH-Wert mit Essigsäure auf 5 - 6 eingestellt wird und die auf 1 Liter Wasser 5-10 g eines Quellmittels, wie o-Phenylphenol und 0,5 g feindispergierten Farbstoff des Beispiels 1 enthält, werden bei 50-60° 25 g Garn aus Polyäthylenglykolterephthalat eingebracht, das Färbebad innerhalb 30 Minuten auf Kochtemperatur erhitzt und 90 Minuten bei dieser Temperatur gehalten. Das so gefärbte Material wird während 20-30 Minuten bei 60-70° mit 4 ml/l Natronlauge (380 Bé) und 2 g/l Dithionit reduktiv nachbehandelt. Danach wird warm gespült, mit Essigsäure abgesäuert und nochmals gespült. SO2C2H5 SO2C2H5 438 "" NHCOCH2CN H "" "439" "NHCOCH3 CH3 crotenyl C4H9 bla 440 "" "C2H5 allyl CH2CH2OH" 441 "" "OCH3" C2H5 "442" "" "" "CH2CH2CN "443" "" "Methallyl CH2CH2OCOCH3" 444 "" "OC2H5 Allyl CH2CH2OH" 445 "" "" "CH2CH2OCOCH3" 446 "" "" "" CH2CH2COOCH3 "447" "" "" "CH2CH2CN" 448 "" "" "C4H9" 449 "" NHCOC2H5 "" CH3 "450" "NHCOOCH3" "C2H5" 451 "" NHCONHC2H5 "" "" 452 "" NHCOCH3 OC2H4OH "" "453" "" OC2H4OCOCH3 "" "454" "" OC2H4Cl "" "455" "" OC2H4CN "" " Example X1 X2 Y Z R1 R2 color 456 SO2N (CH3) NO2 H H allyl CH2CH2CN red 457 "" H H "CH2CH2OCOCH3" 458 '"H H methallyl CH2CH2OH bordo 459 "" H H Crotenyl CH3 "460" CH3 H Allyl CH2CH2CN lt 461 "" "H Methallyl CH2CH2COOCH3" 462 "" C2H5 H Allyl C4H9 "463" "" H "CH2CH2OCOC2H5" 464 "" OCH3 H "CH2CH2-C6H5" 465 "" lt II H crotenyl C 2H5 466 "" OC2H5 H allyl CH2CH2SO2CH3 467 "" "H" CH2CH2OH 468 CH3 OCH3 CH2CH2COOCH red-violet 469 "" NHCOCH3 H "CH3 blue violet 470" "" H "C4H9 471" "" H Methallyl C2H5 472 " "" H crotenyl CH3 473 "" "H allyl CH2CH2OH Example X1 X2 Y Z R1 R2 color 474 SO2N (CH3) 2 NO2 NHCOCH3 H Allyl CH2CH2OCOCH3 red-violet 475 "" "H" CH2CH2CN "476" "" H "CH2CH2-C6H5" 477 "" "H" CH2CH2SO2C2H5 "478" "NHCOC2H5 H" CH2CH2COOCH3 "479" "NHCOC3H7 H" CH2CH2NO2 "480" "NHCOOCH3 H "CH2CH2OCOOCH3" 481 "" NHCONH2 H Methallyl C 2H5 purple 482 "" NHCONHC2H5 H Allyl CH2CH2OCOCH3 red violet 483 lt "NHCONHC3H5 H" CH3 violet 484 "" NHCOCH2Cl H "C2H5" 485 "" NHCOCH2OH H "" "486" "NHCOCH2OCH3 H" "" 487 "" NHCOCH2OCOCH3 H "" "488" "NHCOCH2CN H" "" 489 "" NHCOCH3 CH3 Crotenyl C4H9 blue 490 "according to C2H5 Allyl CH2CH2OH lt 491 "" "OCH3" C2H5 "492" "" "" CH2CH2CN "493" " "" Methallyl CH2CH2OCOCH3 " Example X1 X2 Y Z R1 R2 color 494 SO2N (CH3) 2 NO2 NHCOCH3 OC2H5 allyl CH2CH2OH blue 495 "" "" "CH2CH2OCOCH3" 496 "" "" "CH2CH2COOCH3" 497 "" "" "" CH2CH2CN "498" "" "" "C4H9" 499 "" NHCOC2H5 "" CH3 "500" "NHCOOCH3" "C2H5" 501 according to NHCONHC2H5 "" "502" NHCOCH3 OC2H40H lt II 503 "" "OC2H4OCOCH3" "" 504 "" OC2H4Cl "" "505" "" OC2H4CN "" " 506 "CN H H" CH2CH2CN red 507 "" H H "CH2CH2OCOCH3" 508 "" H H Methallyl CH2CH2OH bord 509 "" H H Crotenyl CH3 "510" "CH3 H Allyl CH2CH2CN" 511 "" "H Methallyl CH2CH2COOCH3 "512" "C2H5 H Allyl C4H9" 513 "" "H" CH2CH2OCOC2H5 " Ex. X1 X2 Y Z R1 R2 Color 514 SO2N (CH3) 2 CN OCH3 H Allyl CH2CH2-C6H5 board 515 "" "H Crotenyl C2H5" 516 "" OC2H5 H Allyl CH2CH2SO2CH3 "517" "" H "CH2CH2OH "518" "CH3 OCH3" CH2CH2COOCH3 red violet 519 "" NHCOCH3 H "CH3 blue violet 520 "" "H" C4H9 "521" "" H Methallyl C2H5 "522" "" H Crotenyl CH3 "523 "" "H Allyl CH2CH2OH" 524 "" "H" CH2CH2OCOCH3 red-violet 525 "" "H" CH2CH2CN "526" "" H "CH2CH2-C6H5" 527 "" "H" CH2CH2SO2C2H5 "528" "NHCOC2H5 H" CH2CH2COOCH3 "529" "NHCOC3H7 H" CH2CH2NO2 "530" "NHCOOCH3 H" CH2CH2OCOOCH3 "531" "NHCONH2 H methallyl C2H5 purple 532" "NHCONHC2H5 H allyl CH2CH2OCOCH3 red-violet Example X1 X2 Y Z R1 R2 color 533 SO2N (CH3) 2 CN NHCONHC3H5 H Allyl CH3 violet 534 "" NHCOCH2Cl H "C2H5" 535 "" NHCOCH2OH H "" "536" "NHCOCH2OCH3 H" "" 537 "" NHCOCH2OCOCH3 H "" "538" "NHCOCH2CN H" "" 539 "" NHCOCH3 CH3 Crotenyl C4H9 blue 540 "" "C2H5 Allyl CH2CH2OH" 541 "" "OCH3 "C2H5" 542 "" "" "CH2CH2CN" 543 "" "" Methallyl CH2CH2OCOCH3 "544" "" OC2H5 Allyl CH2CH2OH "545" "" "" "CH2CH2OCOCH3" 546 "" "" "CH2CH2COOCH3" 547 "" "" "CH2CH2CN" 548 "" "" "C4H9" 549 "" NHCOC2H5 "" CH3 "550" " NHCOOCH3 "" C2H5 "551" "NHCONHC2H5" "" " Example X1 X2 Y Z R1 R2 color 552 SO2N (CH3) 2 CN NHCOCH3 OC2H4OH Allyl C2H5 blue 553 "" "OC2H4OCOCH3 "" "554" "" OC2H4Cl "" "555" "" OC2H4CN "" "Example 556: In a dye liquor, whose pH is adjusted to 5-6 with acetic acid and that to 1 liter of water 5-10 g of a swelling agent such as o-phenylphenol and 0.5 g of finely dispersed dye of Example 1 contains 25 g of polyethylene glycol terephthalate yarn at 50-60 ° introduced, the dyebath heated to boiling temperature within 30 minutes and 90 Maintained at this temperature for minutes. The material thus colored will last for 20-30 Minutes at 60-70 ° with 4 ml / l sodium hydroxide solution (380 Bé) and 2 g / l dithionite reductive post-treated. It is then rinsed warm, acidified with acetic acid and again flushed.
Man erhält so eine klare rotstichig blaue Färbung mit sehr guten Echtheitseigenschaften. This gives a clear, reddish-tinged blue coloration with very good results Authenticity properties.
Beispiel 557: Mit einer Klotzflotte, die auf 1 Liter Wasser 2-3 g eines Äthylenoxydanlagerungsprodukts als Dispergiermittel, 20 g eines Verdickungsmittels auf Polyacrylsäurebasis und 2 g feindispergierten Farbstoff des Beispiels 1 enthält, wird ein Gewebe aus Polyäthylenglykolterephthalat bei 400 geklotzt, getrocknet und mit Heißluft von 200-230° 60 Sekunden thermosoliert Nach einer reduktiven Nachbehandlung mit 4 ml/l Natronlauge (380 se) und 2 g/l Dithionit während 20 Minuten bei 60-70° wird das Material gespült, abgesäuert und nochmals gespült.Example 557: With a padding liquor that is 2-3 g of an ethylene oxide addition product as a dispersant, 20 g of a thickener contains based on polyacrylic acid and 2 g of finely dispersed dye of Example 1, a fabric made of polyethylene glycol terephthalate is padded at 400, dried and thermosolated with hot air at 200-230 ° for 60 seconds after a reductive aftertreatment with 4 ml / l sodium hydroxide solution (380 se) and 2 g / l dithionite for 20 minutes at 60-70 ° the material is rinsed, acidified and rinsed again.
Man erhält so eine klare rotstichig blaue Färbung mit sehr guten Echtheitseigenschaften.A clear, reddish-tinged blue dyeing with very good fastness properties is obtained in this way.
Beispiel 558: Ein Gewebe aus Polyester wird auf einer Rouleauxdruckmaschine mLt eLner Druckpaste folgender Zusammensetzung bedruckt: 50 g 10%iger Farbstoffteig, der den Farbstoff des Beispiels 3 in feindispergierter Form enthält, 250 g Stärke-Traganthverclickung, 250 g Kristallgummiverdickung (1:3 ) und 450 g Wasser oder Verdickung. Nach dem Drucken und Trocknen wird das Gewebe entweder 30-60 Sekunden bei 190-210° thermosoliert oder 10-20 Minuten bei 1-2 atü gedämpft. Nach beiden Methoden werden rotstichig blaue Drucke von sehr guten Eciitheitseigenschaften erhalten.Example 558: A polyester fabric is printed on a roller printing machine mLt eLner printing paste printed with the following composition: 50 g 10% dye paste, which contains the dye of Example 3 in finely dispersed form, 250 g of starch tragacanth 250 g crystal rubber thickening (1: 3) and 450 g water or thickening. After this Printing and drying, the fabric is either thermosolated for 30-60 seconds at 190-210 ° or steamed for 10-20 minutes at 1-2 atm. Both methods will turn reddish obtained blue prints of very good ecological properties.
Claims (6)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE759836D BE759836A (en) | 1969-12-12 | WATER INSOLUBLE MONOAZOIC COLORANTS AND THEIR PREPARATION | |
| DE19691962402 DE1962402A1 (en) | 1969-12-12 | 1969-12-12 | Water-insol monazo dyes for hydrophobic - materials |
| NL7017480A NL7017480A (en) | 1969-12-12 | 1970-11-30 | |
| CA099817A CA937566A (en) | 1969-12-12 | 1970-12-04 | Water-insoluble monoazo dyes |
| JP10899770A JPS4817735B1 (en) | 1969-12-12 | 1970-12-10 | |
| JP10899870A JPS4817736B1 (en) | 1969-12-12 | 1970-12-10 | |
| JP10899970A JPS4817737B1 (en) | 1969-12-12 | 1970-12-10 | |
| JP45109000A JPS4817738B1 (en) | 1969-12-12 | 1970-12-10 | |
| GB5897670A GB1313209A (en) | 1969-12-12 | 1970-12-11 | Water-insoluble monoazo dyes |
| FR7044684A FR2070831B1 (en) | 1969-12-12 | 1970-12-11 | |
| CH1839870A CH549078A (en) | 1969-12-12 | 1970-12-11 | PROCESS FOR THE PREPARATION OF HYDRO-INSOLUBLE MONOAZO DYES. |
| CH1839970A CH549083A (en) | 1969-12-12 | 1970-12-11 | PROCESS FOR THE PREPARATION OF HYDRO-INSOLUBLE MONOAZO DYES. |
| ES386343A ES386343A1 (en) | 1969-12-12 | 1970-12-11 | Water-insoluble monoazo dyes |
| SU1499786A SU439992A1 (en) | 1970-12-11 | The method of obtaining water-insoluble monoazoses | |
| CH1840070A CH549084A (en) | 1969-12-12 | 1970-12-11 | PROCESS FOR THE PREPARATION OF HYDRO-INSOLUBLE MONOAZO DYES. |
| AT1115870A AT297176B (en) | 1969-12-12 | 1970-12-11 | Process for the production of new, water-insoluble monoazo dyes |
| ES0389342A ES389342A1 (en) | 1969-12-12 | 1970-12-11 | Procedure for the obtaining of insoluble monoazoic colorants in water. (Machine-translation by Google Translate, not legally binding) |
| CH1840170A CH540321A (en) | 1969-12-12 | 1970-12-11 | Process for the preparation of water-insoluble monoazo dyes |
| AT1115970A AT297877B (en) | 1969-12-12 | 1970-12-11 | Process for the production of new, water-insoluble monoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691962402 DE1962402A1 (en) | 1969-12-12 | 1969-12-12 | Water-insol monazo dyes for hydrophobic - materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1962402A1 true DE1962402A1 (en) | 1971-06-16 |
Family
ID=5753711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691962402 Pending DE1962402A1 (en) | 1969-12-12 | 1969-12-12 | Water-insol monazo dyes for hydrophobic - materials |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS4817738B1 (en) |
| CH (1) | CH540321A (en) |
| DE (1) | DE1962402A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56167758A (en) * | 1980-04-28 | 1981-12-23 | Cassella Farbwerke Mainkur Ag | Water-insoluble azo dye, its manufacture and coloring and printing method therewith |
| JPS58210962A (en) * | 1982-06-02 | 1983-12-08 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57132937U (en) * | 1981-02-04 | 1982-08-19 |
-
1969
- 1969-12-12 DE DE19691962402 patent/DE1962402A1/en active Pending
-
1970
- 1970-12-10 JP JP45109000A patent/JPS4817738B1/ja active Pending
- 1970-12-11 CH CH1840170A patent/CH540321A/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56167758A (en) * | 1980-04-28 | 1981-12-23 | Cassella Farbwerke Mainkur Ag | Water-insoluble azo dye, its manufacture and coloring and printing method therewith |
| JPH0216343B2 (en) * | 1980-04-28 | 1990-04-16 | Cassella Ag | |
| JPS58210962A (en) * | 1982-06-02 | 1983-12-08 | Mitsubishi Chem Ind Ltd | Monoazo dye for polyester fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| CH540321A (en) | 1973-08-15 |
| JPS4817738B1 (en) | 1973-05-31 |
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