DE2338973B2 - Monoazo pigments, process for their production and their use - Google Patents
Monoazo pigments, process for their production and their useInfo
- Publication number
- DE2338973B2 DE2338973B2 DE2338973A DE2338973A DE2338973B2 DE 2338973 B2 DE2338973 B2 DE 2338973B2 DE 2338973 A DE2338973 A DE 2338973A DE 2338973 A DE2338973 A DE 2338973A DE 2338973 B2 DE2338973 B2 DE 2338973B2
- Authority
- DE
- Germany
- Prior art keywords
- acetoacetylamino
- benzimidazolone
- chloro
- yellow
- methyl
- 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
Links
Classifications
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
-
- 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Description
2. Das Monoazopigment der Formel Cl2. The monoazo pigment of the formula Cl
C=OC = O
NHCOCH3 NHCOCH 3
3. Das Monoazopigment der Formel3. The monoazo pigment of the formula
C1 COCH3 C1 COCH 3
N= N-CH CONH-/V NHn N = N-CH CONH- / V NHn
C=OC = O
ClCl
4. Das Monoazopigment der Formel COCH3 4. The monoazo pigment of the formula COCH 3
N=N-CHCONHn^VNHx„ , ^NH''N = N-CHCONHn ^ V NHx ", ^ NH"
NHCOCH3 NHCOCH 3
3535
4040
4545
5050
5555
NH\
NH'NH \
NH '
C=OC = O
5. Das Monoazopigment der Formel
COCH3 5. The monoazo pigment of the formula
COCH 3
N=N-CH-CONh-I^Y'NHx N = N-CH-CONh-I ^ Y ' NHx
NH'NH '
-Cl-Cl
C=OC = O
NHCONHCO
6. Verfahren zur Herstellung von Monoazopigmenten gemäß Anspruch 1, dadurch gekennzeichnet, daß man diazotierte aromatische Amine der allgemeinen Formel6. Process for the production of monoazo pigments according to claim 1, characterized in that that one diazotized aromatic amines of the general formula
ZCONH-{TJZCONH- {TJ
worin die Gruppe —NHCOZ in meta- oder paraStellung zur Aminogruppe steht, mit Kupplungskomponenten der allgemeinen Formelwherein the group —NHCOZ is in the meta or para position to the amino group, with coupling components of the general formula
CH3COCH2CONHCH 3 COCH 2 CONH
NH'NH '
C=OC = O
worin R, X1, X2 und Z die im Anspruch 1 angegebene 3edeutung besitzen, kuppelt.wherein R, X 1 , X 2 and Z have the meaning given in claim 1, couples.
7. Verfahren zum Färben bzw. Bedrucken von Lacken, Lackbildern, Lösungen und Produkten aus Acetylcellulose, natürlichen Harzen oder Kunstharzen, Polystyrol, Polyolefinen, Polyacrylverbindungen, Polyvinylverbindungen, Polyestern. Gummi, Casein- oder Siliconharzen, ferner Papier oder Textilfasern aus Cellulose, Celluloseäthern. Celluloseestern, Polyamiden oder Polyurethanen, dadurch gekennzeichnet, daß man Monoazopigmente nach Anspruch 1 verwendet.7. Process for coloring or printing lacquers, lacquer images, solutions and products Acetyl cellulose, natural or synthetic resins, polystyrene, polyolefins, polyacrylic compounds, Polyvinyl compounds, polyesters. Rubber, casein or silicone resins, as well as paper or textile fibers made from cellulose, cellulose ethers. Cellulose esters, polyamides or polyurethanes, characterized in that monoazo pigments according to Claim 1 are used.
Die vorliegende Erfindung betrifft wertvolle Monoazopigmente der allgemeinen FormelThe present invention relates to valuable monoazo pigments of the general formula
χ..χ ..
ZCONH —;ZCONH -;
COCH3 COCH 3
V-N=N-CHCONHV-N = N-CHCONH
worin R, X1 und X2 gleich oder verschieden sind und ein Wasserstoffatom, ein Chlor- oder Bromatom, diewherein R, X 1 and X 2 are identical or different and represent a hydrogen atom, a chlorine or bromine atom, the
Methyl-, Äthyl-, Methoxy- oder Athoxygruppe und Z die Methyl- oder Äthylgruppe oder ein Phenylrest, der ein oder zwei Chlor- oder Bromatome, Methyloder Methoxygruppen als Substituenten aufweisen kann, ist und worin die Gruppe —NHCOZ in meta- oder para-Stellung zur Azogruppe steht.Methyl, ethyl, methoxy or ethoxy group and Z the methyl or ethyl group or a phenyl radical, which can have one or two chlorine or bromine atoms, methyl or methoxy groups as substituents, and in which the group —NHCOZ in meta- or para Position to the azo group.
Gegenüber solchen nächstvergleichbaren Pigmenten aus der DT-OS 18 08 017, die ebenfalls eine Acylaminogruppe und zusätzlich eine Methylgruppe im Benzimidazolylring haben, zeichnen sich die erfindungsgemäßen Pigmente durch eine bessere Ausblutechtheit aus.Compared to such next comparable pigments from DT-OS 18 08 017, which is also a Have acylamino group and additionally a methyl group in the benzimidazolyl ring, those according to the invention are distinguished Pigments are characterized by better resistance to bleeding.
Gegenstand der Erfindung ist weiterhin ein Verfahren zur Herstellung obengenannter Azopigmente, bei dem man diazotierte aromatische Amine der allgemeinen FormeiThe invention also relates to a process for the production of the abovementioned azo pigments which one diazotized aromatic amines of the general formula
ZCONH—ZCONH—
NH,NH,
worin die Gruppe —NHCOZ in meta- oder paraStellung zur Aminogruppe steht, mit Kupplungskomponenten der allgemeinen Formelwherein the group —NHCOZ is in the meta or para position to the amino group, with coupling components of the general formula
CH3COCH2CONH —/\
RCH 3 COCH 2 CONH - / \
R.
NH-NH-
C=OC = O
worin R, X1, X2 und Z die vorstehend angegebene Bedeutung besitzen, kuppelt.wherein R, X 1 , X 2 and Z are as defined above, couples.
Die als Diazokomponenten eingesetzten Amine sind größtenteils bereits bekannt und/oder lassen sich nach bekannten Methoden herstellen, beispielsweise durch Nitrieren und anschließendes Reduzieren eines entsprechend substituierten Acylaminobenzols der allgemeinen FormelMost of the amines used as diazo components are already known and / or can be reduced produce known methods, for example by nitriding and then reducing a corresponding substituted acylaminobenzene of the general formula
X,X,
4545
NHCOZNHCOZ
wobei X1, X2 und Z die vorstehend angegebene Bedeutung besitzen. Als Diazokomponenten können beispielsweise verwendet werden:where X 1 , X 2 and Z have the meanings given above. The following can be used as diazo components, for example:
3-Amino-acetanilid, ^Chlor-S-amino-acetanilid.3-Amino-acetanilide, ^ chloro-S-amino-acetanilide.
4,6-Dichlor-3-amino-acetanüid,4,6-dichloro-3-amino-acetanide,
4-Brom-3-amino-acetanilid,4-bromo-3-amino-acetanilide,
4,6-Dibrom-3-amino-acetanilid,4,6-dibromo-3-amino-acetanilide,
4-Chlor-6-methyl-3-amino-acetanilid, 4-Brom-6-methyl-3-amino-acetanilid,4-chloro-6-methyl-3-amino-acetanilide, 4-bromo-6-methyl-3-amino-acetanilide,
o-Chlor-S-amino-acetanilid,o-chloro-S-amino-acetanilide,
6-Methyl-3-amino-acetanilid,6-methyl-3-amino-acetanilide,
4-Ä t hyl-3-amino-acetanilid,4-ethyl-3-amino-acetanilide,
4,6-Dimethoxy-3-amino-acetanilid, 4-Ätho.<y-3-amino-acetanilid,4,6-dimethoxy-3-amino-acetanilide, 4-etho. <Y-3-amino-acetanilide,
3-Amino-propionanilid,3-amino-propionanilide,
4-Chlor-3-amino-propionanilid,4-chloro-3-aminopropionanilide,
4-Chlor-6-methyl-3-amino-propionanilid,4-chloro-6-methyl-3-aminopropionanilide,
4-Methoxy-3-amino-propionanilid, 3-Benzoylamino-anilin,4-methoxy-3-aminopropionanilide, 3-benzoylamino-aniline,
3-(2'-Chlor-benzoylamino)-aniliii.3- (2'-chloro-benzoylamino) -aniliii.
3-(4'-Chlor-3'-methyl-bcnzoylamino)-aniliii, 3-{2',4'-Dichlor-benzoyIamino)-aniün, 3-(2',5'-Dibrom-benzoylamino)-anilin, l-Chlor-S-benzoylamino-anilin, 2-Chlor-5-(4'-chlor-benzoylamino)-anilin, 2-Chlor-5-(2',5'-dichlor-benzoylamino)-anilin, 2-Chlor-5-(4'-methoxy-benzoylamino)-anilin, 2,4-Dichlor-5-benzoylamino-anilin, 2,4-Dichlor-5-(2',4'-dichlor-benzoylamino)-3- (4'-chloro-3'-methyl-benzoylamino) -aniliii, 3- {2 ', 4'-dichloro-benzoylamino) -aniline, 3- (2', 5'-dibromo-benzoylamino) -aniline, l-chloro-S-benzoylamino-aniline, 2-chloro-5- (4'-chloro-benzoylamino) -aniline, 2-chloro-5- (2 ', 5'-dichloro-benzoylamino) -aniline, 2-chloro-5- (4'-methoxy-benzoylamino) -aniline, 2,4-dichloro-5-benzoylamino-aniline, 2,4-dichloro-5- (2 ', 4'-dichloro-benzoylamino) -
anilin,
2,4-Dichlor-5-(4'-chlor-2'-methyl-benzoylamino)-anilin,
aniline,
2,4-dichloro-5- (4'-chloro-2'-methyl-benzoylamino) -aniline,
2,4-Dichlor-5-(4'-brom-benzoylamino)-anilin, 2-Chlor-4-methyI-5-benzoylamino-anilin, 2-Chlor-4-methyl-5-(2'-chlor-benzoylamino)-2,4-dichloro-5- (4'-bromo-benzoylamino) -aniline, 2-chloro-4-methyl-5-benzoylamino-aniline, 2-chloro-4-methyl-5- (2'-chloro-benzoylamino) -
anilin,
2-Chlor-4-methyl->(3'-chlor-benzoylamino)-aniline,
2-chloro-4-methyl ->(3'-chloro-benzoylamino) -
anilin,
2-Chlor-4-methyl-5-(2\5'-dichlor-benzoylamino
!-anilin,aniline,
2-chloro-4-methyl-5- (2 \ 5'-dichloro-benzoylamino! -Aniline,
2-Brom-5-benzoylanüno-anilin, 2-Brom-5-(2\4'-dichlor-benzoylamino)-anilin, 2-Methyl-5-benzoylamino-anilin, 2-Methyl-5-(4'-chlor-benzoylamino)-anilin, 2-Methyl-5-(2',5'-dichlor-benzoylamino)-anilin, 4-Methyl-5-(2',4'-dichlor-benzoylaniino)-anilin, 4-Met!iyl-5-(4'-chlor-2'-methoxy-benzoylaminoj anilin.2-bromo-5-benzoylanüno-aniline, 2-bromo-5- (2 \ 4'-dichloro-benzoylamino) -aniline, 2-methyl-5-benzoylamino-aniline, 2-methyl-5- (4'-chloro-benzoylamino) -aniline, 2-methyl-5- (2 ', 5'-dichloro-benzoylamino) -aniline, 4-methyl-5- (2 ', 4'-dichloro-benzoylaniino) -aniline, 4-methyl-5- (4'-chloro-2'-methoxy-benzoylaminoj aniline.
I-Methoxy-S-benzoylamino-anilin, 2-Methoxy-5-(2'-chlor-benzoylamino)-anilin, 2-Methoxy-5-(4'-chlor-3'-methyl-benzoyl-I-methoxy-S-benzoylamino-aniline, 2-methoxy-5- (2'-chloro-benzoylamino) -aniline, 2-methoxy-5- (4'-chloro-3'-methyl-benzoyl-
amino)-anilin,
4-Aminoacetanilid,
2-Chlor-4-amino-acetanilid, 3-Chlor-4-amino-acetanilid, 2,5-Dichlor-4-amino-acetanilid,
2,6-Dichlor-4-amino-acetanilid, 2-Brom-4-amino-acetanilid,
2-Ciilor-5-methyl-4-amino-acetanilid, 5-Chlor-2-methyl-4-amino-acetanilid,
2-M<;thyl-4-amino-acetanilid, S-Methyl^-amino-acetanilid,
2-Methoxy-4-amino-acetanilid, 2-Methoxy-5-methyl-4-amino-acetanilid, 2,5-Dimethoxy-4-amino-acetanilid,
2,5-Dichlor-4-amino-propionanilid, 4- Benzoy lamino- anilin,
4-(2 .5'-Dichlor-benzoylaminoJ-anilin,
4-(4'-Brom-benzoylamino)-anilin, 2-Chlor-4-benzoylamino-anilin, 3-Chlor-4-(4'-chlor-3'-methyl-benzoylamino)-anilin.
amino) -aniline,
4-aminoacetanilide,
2-chloro-4-amino-acetanilide, 3-chloro-4-amino-acetanilide, 2,5-dichloro-4-amino-acetanilide, 2,6-dichloro-4-amino-acetanilide, 2-bromo-4- amino-acetanilide, 2-Ciilor-5-methyl-4-amino-acetanilide, 5-chloro-2-methyl-4-amino-acetanilide, 2-M <; thyl-4-amino-acetanilide, S-methyl ^ - amino-acetanilide, 2-methoxy-4-amino-acetanilide, 2-methoxy-5-methyl-4-amino-acetanilide, 2,5-dimethoxy-4-amino-acetanilide, 2,5-dichloro-4-amino propionanilide, 4- Benzoy lamino-aniline,
4- (2 .5'-dichloro-benzoylaminoJ-aniline, 4- (4'-bromo-benzoylamino) -aniline, 2-chloro-4-benzoylamino-aniline, 3-chloro-4- (4'-chloro-3 '-methyl-benzoylamino) -aniline.
2,5-Dichlor-4-benzoylamino-anilin, 2,5-Dichlor-4-(4'-chlor-2'-methoxy-benzoyl-2,5-dichloro-4-benzoylamino-aniline, 2,5-dichloro-4- (4'-chloro-2'-methoxy-benzoyl-
amino)-anilin,
2-Chlor-5-methyl-4-(2',4'-dichlor-benzoylamino)-anilin, amino) -aniline,
2-chloro-5-methyl-4- (2 ', 4'-dichloro-benzoylamino) -aniline,
S-Chlor-^-methyW-benzoylamino-anilin,
5-Chlor-2-methyl-4-(4'-chlor-2'-methoxybenzoylamino)-anilin,
2,5-Dimethoxy-4-(4'-chlor-benzoy!amino)-S-chlorine - ^ - methyW-benzoylamino-aniline, 5-chloro-2-methyl-4- (4'-chloro-2'-methoxybenzoylamino) -aniline,
2,5-dimethoxy-4- (4'-chloro-benzoy! Amino) -
anilin,
2-Chlor-5-methyl-4-(2',3',4'-trichlorbenzoylamino)-anilin. aniline,
2-chloro-5-methyl-4- (2 ', 3', 4'-trichlorobenzoylamino) aniline.
Die als Kupplungskomponenten eingesetzten A bindungen sind größtenteils bekannt und können η bekannten Verfahren hergestellt werden, beispielsw durch Umsetzungeines 5-Amino-benzimidazolonsThe A bonds used as coupling components are largely known and can η known processes, for example by reacting a 5-amino-benzimidazolone
IOIO
Diketen. Als geeignete Kupplungskomponenten seien genannt:Diketones. Suitable coupling components are:
S-Acetoacetylamino-benzimidazolon,S-acetoacetylamino-benzimidazolone,
ö-Chlor-S-acetoacetylamino-benzimidazolon,ö-chloro-S-acetoacetylamino-benzimidazolone,
T-Chlor-S-acetoacetylamino-benzimidazolon,T-chloro-S-acetoacetylamino-benzimidazolone,
o-Brom-S-acetoacetylamino-benzimidazolon,o-bromo-S-acetoacetylamino-benzimidazolone,
7-Brom-5-acetoacetylamino-benzimidazolon,7-bromo-5-acetoacetylamino-benzimidazolone,
o-Methyl-S-acetoacetylamino-benzimidazolon, T-Methyl-S-acetoacetylamino-benzimidazoles 7-Äthyl-5-acetoacetylamino-benziπlidazolon,o-methyl-S-acetoacetylamino-benzimidazolone, T-methyl-S-acetoacetylamino-benzimidazoles 7-ethyl-5-acetoacetylamino-benziπlidazolon,
T-Methoxy-S-acetoacetylamino-benzimidazolon, 7-Äthoxy-5-acetoacetylamino-benzimidazolon.T-methoxy-S-acetoacetylamino-benzimidazolone, 7-ethoxy-5-acetoacetylamino-benzimidazolone.
Die Kupplungsreaktion erfolgt in bekannter Weise, beispielsweise in wäßrigem Medium, gegebenenfalls in Gegenwart nichtionogener, anionaktiver oder kationaktiver Dispergiermittel und/oder organischer Lösungsmittel. Die Kupplung kann auch in organischen Lösungsmitteln durchgeführt werden.The coupling reaction takes place in a known manner, for example in an aqueous medium, if appropriate in the presence of nonionic, anionic or cationic dispersants and / or organic solvents. The coupling can also be carried out in organic solvents.
Zur Erzielung der optimalen Farbstärke und einer besonders günstigen Kristallstruktur ist es häufig zweckmäßig, das Kupplungsgemisch einige Zeit zu erhitzen, beispielsweise zum Kochen oder unter Druck auf Temperaturen über IO0C zu bringen, gegebenenfalls in Gegenwart organischer Lösungsmittel wie Dichlorbenzol oder Dimethylformamid oder von Harzseife. Besonders reine und echte Färbungen erhält man mit den erfindungsgemäßen Pigmenten, wenn man sie nach der Kupplung als feuchte Preßkuchen oder als getrocknete Pulver einer Nachbehandlung mit organischen Lösungsmitteln wie Pyridin. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Alkoholen, Glykol, Glykolmonomethyläther, Eisessig, Chlorbenzol, Dichlorbenzol oder Nitrobenzol bei Siedetemperatur oder unter Druck bei erhöhter Temperatur unterwirft oder eine Mahlung der Pigmente unter Zusatz von Mahlhilfsmitteln anschließt. In einigen Fällen gelingt die überführung in eine besonders günstige Kristallstruktur auch durch Erhitzen mit Wasser zum Kochen oder auf höhere Temperaturen unter Druck, gegebenenfalls unter Zusatz von Dispergiermitteln sowie gegebenenfalls unter Zusatz von organischen Lösungsmitteln, beispielsweise der vorstehend genannten Art. Die Pigmente können auch in Gegenwart von Trägern bstanzen, die zur Farblackherstellung geeignet sind, gekuppelt werden.It is often used to achieve optimal color strength and a particularly favorable crystal structure expedient to heat the coupling mixture for some time, for example to boil or under To bring pressure to temperatures above 10 ° C., if necessary in the presence of organic solvents such as dichlorobenzene or dimethylformamide or from resin soap. Particularly pure and real colors are obtained with the pigments according to the invention if they are obtained as a moist press cake after coupling or as a dried powder after treatment with organic solvents such as pyridine. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, alcohols, glycol, glycol monomethyl ether, Glacial acetic acid, chlorobenzene, dichlorobenzene or nitrobenzene at boiling temperature or under pressure subjected at elevated temperature or followed by grinding of the pigments with the addition of grinding aids. In some cases, the transformation into a particularly favorable crystal structure also succeeds Heating with water for boiling or at higher temperatures under pressure, if necessary with addition of dispersants and optionally with the addition of organic solvents, for example of the type mentioned above. The pigments can also be punched in the presence of carriers, which are suitable for the production of colored lacquers.
Die neuen Pigmente eignen sich ?"r Herstellung von Druckfarben, Lackfarben und Dispersions-Anstrichfarben, zum Färben von Kautschuk, Kunststoffen und natürlichen oder synthetischen Harzen. Die neuen Pigmente sind ferner geeignet für den Pigmentdruck auf Substraten, insbesondere Textilfasermaterialien oder anderen flächenförmigen Gebilden, wie beispielsweise Papier. Die Pigmente können auch für andere Anwendungszwecke, z. B. in feinverteilter Form zum Färben von Kunstseide aus Viskose oder Cellulose äthern bzw. -estern, Polyamiden, Polyurethanen, PoIyglykolterephthalateri oder Polyacrylnitril in der Spinnmasse oder zum Färben von Papier verwendet werden.The new pigments are suitable for the production of Printing inks, lacquer paints and dispersion paints, for coloring rubber, plastics and natural or synthetic resins. The new pigments are also suitable for pigment printing on substrates, in particular textile fiber materials or other sheet-like structures, such as, for example Paper. The pigments can also be used for other purposes, e.g. B. in finely divided form for Dyeing of rayon or cellulose rayon, ethers or esters, polyamides, polyurethanes, polyglycol terephthalate or polyacrylonitrile can be used in the spinning pulp or for dyeing paper.
Die neuen Pigmente lassen sich in den genannten Medien gut verarbeiten. Die Färbungen weisen sehr gute Licht-, Wetter- und Migrationsechtheiten auf und sind gegen Hitzeeinwirkung und den Einfluß von Chemikalien, z.B. Lösungsmitteln, beständig.The new pigments can be easily processed in the media mentioned. The colorations are very wise good light, weather and migration fastness properties and are against the effects of heat and the influence of Resistant to chemicals, e.g. solvents.
Durch ihre hervorragenden Echtheiten zeichnen sich von den erfindungsgemäßen Pigmenten insbesondere folgende aus:The pigments according to the invention are particularly notable for their excellent fastness properties the following:
NHCOCH3 NHCOCH 3
COCH3
-CHCONHCOCH 3
-CHCONH
/VNHN/ V NH N
NH-NH-
C=OC = O
COCH3 COCH 3
CHCONHCHCONH
NH ^ NH ^
NH \NH \
C=OC = O
COCH3 COCH 3
N=N- CHCONH—ZVNHx ( N = N- CHCONH — ZV NHx (
ci-y σci-y σ
NHCO-^f >-CINHCO- ^ f> -CI
21,9 g 4,6 - Dichlor - 3 - amino - acetanilid werden mit 100 ml Eisessig und 30 ml 31%iger Salzsäure 2 Stunden bei Raumtemperatur verrührt und anschließend bei O bis 5°C mit 21 ml 5n-Natriumnitritlösung diazotiert. Man läßt 30 Minuten nachrühren, zerstört den Nitritüberschuß mit Amidosulfonsäure und klärt.21.9 g of 4,6 - dichloro - 3 - amino - acetanilide become stirred with 100 ml of glacial acetic acid and 30 ml of 31% hydrochloric acid for 2 hours at room temperature and then diazotized at 0 to 5 ° C with 21 ml of 5N sodium nitrite solution. The mixture is left to stir for 30 minutes, destroys the excess nitrite with sulfamic acid and clears.
24,4 g 5 - Acetoacetylamino - benzimidazolon werden in einer Mischung aus 500 ml Wasser, 27 ml 33%iger Natronlauge und 5 ml einer 10%igen wäßrigen Lösung des Reaktionsproduktes aus 1 Mol Stearylalkohol und 20 Mol Äthylenoxid gelöst. Bei 15 bis 20° C wird die Kupplungskomponente durch Einstürzen von 17,5 ml Eisessig ausgefällt. Anschließend wird bei 20° C die Diazoniumsalzlösung langsam zur Suspension der Kupplungskomponente zulaufen lassen. Der pH-Wert wird durch gleichzeitigen Zulauf von etwa 365 ml 5 η-Natronlauge bei etwa 6,3 gehalten. Nach beendeter Kupplung erhitzt man auf95r C und hält 30 Minuten bei dieser Temperatur. Anschließend wird abfiltriert, gewaschen und getrocknet.24.4 g of 5-acetoacetylamino-benzimidazolone are dissolved in a mixture of 500 ml of water, 27 ml of 33% strength sodium hydroxide solution and 5 ml of a 10% strength aqueous solution of the reaction product of 1 mol of stearyl alcohol and 20 mol of ethylene oxide. At 15 to 20 ° C, the coupling component is precipitated by collapsing 17.5 ml of glacial acetic acid. The diazonium salt solution is then slowly run into the suspension of the coupling component at 20.degree. The pH is kept at about 6.3 by simultaneously adding about 365 ml of 5η sodium hydroxide solution. After the coupling has ended is heated auf95 r C, holding 30 minutes at that temperature. It is then filtered off, washed and dried.
42 g des trockenen Pigment pul vers werden mit 45OmI Dimethylformamid !Stunde am Rückfluß gekocht. Nach Abkühlen auf S(V Γ «/ii-H ..κ,,»- 42 g of the dry pigment powder are refluxed with 45OmI dimethylformamide for 1 hour cooked. After cooling down to S (V Γ «/ ii-H ..κ ,,» -
mit Wasser gewaschen, getrocknet und gemahlen. Das so erhaltene Monoazopigmenl der Formelwashed with water, dried and ground. The thus obtained monoazopigmenl of the formula
COCH.,COCH.,
= N-CH-CONH-/NYNHx = N-CH-CONH- / N Y NHx
xAxA
C = OC = O
NHCOCH.,NHCOCH.,
IOIO
zeigt beim Einarbeiten in einen Lack, in eine Druckfarbe, in Polyvinylchlorid oder in eine Spinnmasse sehr reine, orangegelbe Färbungen von vorzüglicher Licht- und Migrationsechtheit.shows when incorporated into a varnish, a printing ink, polyvinyl chloride or a spinning mass very pure, orange-yellow colorations with excellent light and migration fastness.
18,5 g 4 - Chlor - 3 - amino - acetanilid werden mit 100 ml Eisessig und 25 ml konzentrierter Salzsäure 2 Stunden bei Raumtemperatur verrührt und anschließend bei 0 bis 10'C mit 20,5ml 5n-Natriumnitritlösung diazotiert. Man läßt 30 Minuten nachrühren, zerstört den Nitritüberschuß mit Amidosulfonsäure und klärt. Anschließend wird die Diazoniumsalzlösung bei Raumtemperatur allmählich zu einer vorgelegten Suspension von 28.1 g 7-Chlor-5 - aceloacetylamino - benzimidazolon in 350 ml Pyridin zulaufen lassen. Nach beendetem Zulauf wird 1 Stunde nachgerührt und anschließend abfiltriert, mit Wasser gewaschen und bei 60"C getrocknet. 48 g des trockenen Pigmenlpulvers werden mit 580 ml Eisessig I Stunde unter Rückfluß gekocht. Nach Abkühlung auf 50'C wird abgesaugt, mit Wasser gewaschen, getrocknet und gemahlen. Das so erhaltene Monoazopigment der Formel18.5 g of 4-chloro-3-amino-acetanilide are added 100 ml of glacial acetic acid and 25 ml of concentrated hydrochloric acid are stirred for 2 hours at room temperature and then at 0 to 10'C with 20.5ml of 5N sodium nitrite solution diazotized. The mixture is left to stir for 30 minutes and the excess nitrite is destroyed with sulfamic acid and clarifies. The diazonium salt solution is then gradually increased at room temperature a suspension of 28.1 g of 7-chloro-5 - Add aceloacetylamino - benzimidazolone in 350 ml of pyridine. When the feed is complete Stirred for 1 hour and then filtered off, washed with water and dried at 60.degree. 48 g of the dry pigment powder are refluxed with 580 ml of glacial acetic acid for 1 hour. To Cooling to 50 ° C. is filtered off with suction, washed with water, dried and ground. The thus obtained Monoazo pigment of the formula
COCHCOCH
C=OC = O
NHCOCH3 NHCOCH 3
ergibt beim Einarbeiten in eine Druckfarbe, in Polyvinylchlorid, in einen Lack oder eine Spinnmasse sehr reine, grünstichiggelbe Färbungen von hervorragender Lichtechtheit und einwandfreier Migrationsechtheit.when incorporated into a printing ink, polyvinyl chloride, varnish or spinning mass, results in a great deal pure, greenish yellow dyeings of excellent lightfastness and perfect migrationfastness.
19,9 g 2 - Chlor - 5 - methyl - 4 - amino - acetanilid werden in 80 ml 5 η-Salzsäure etwa 1 Stunde verrührt. Anschließend verdünnt man mit Eiswasser auf etwa 250 ml und diazotiert bei 0 bis 5° C langsam mit 20,5 ml 5n-Natriumnitritlösung. Man läßt 30 Minuten nachrühren, zerstört den Nitritüberschuß mit Amidosulfonsäure und klärt.19.9 g of 2-chloro-5-methyl-4-amino-acetanilide are stirred in 80 ml of 5 η hydrochloric acid for about 1 hour. Then it is diluted with ice water about 250 ml and slowly diazotized at 0 to 5 ° C with 20.5 ml of 5N sodium nitrite solution. Leave for 30 minutes stir, destroy the excess nitrite with sulfamic acid and clear.
23,5 g 5 - Acetoacetylamino - benzimidazolon werden in 300 ml Wasser angeschlämmt und durch Zugabe von 75 ml 2n-Natronlauge gelöst. Die geklärte alkalische Lösung tropft man gleichzeitig mit der Diazoniumsalzlösung im Laufe von 2 Stunden bei lObis 15° C zu einer vorgelegten Mischung aus 100 ml 4n-Natriumacetatlösung, 20 ml Eisessig und 10 ml einer 10%igen wäßrigen Lösung des Reaktionsproduktes aus 1 Mol Stearylalkohol und 20 Mol Äthylenoxid. Nach beendeter Kupplung wird die Pigmentsuspension 1 Stunde auf 900C erhitzt. Man saugt das Pigment heiß ab, wäscht mit Wasser salzfrei, trocknet bei 60° C und verrührt das gemahlene Produkt in 300 ml Dimethylformamid. Nach lOminutigem Erhitzen auf 6O0C wird das Pigment abgesaugt, mit Methanol gewaschen, getrocknet und gemahlen.23.5 g of 5-acetoacetylamino-benzimidazolone are suspended in 300 ml of water and dissolved by adding 75 ml of 2N sodium hydroxide solution. The clarified alkaline solution is added dropwise simultaneously with the diazonium salt solution in the course of 2 hours at 10 to 15 ° C to a mixture of 100 ml of 4N sodium acetate solution, 20 ml of glacial acetic acid and 10 ml of a 10% aqueous solution of the reaction product of 1 mol of stearyl alcohol and 20 moles of ethylene oxide. After the coupling has ended, the pigment suspension is heated to 90 ° C. for 1 hour. The pigment is filtered off with suction while hot, washed salt-free with water, dried at 60 ° C. and the ground product is stirred in 300 ml of dimethylformamide. After lOminutigem heating at 6O 0 C, the pigment is filtered off with suction, washed with methanol, dried and ground.
Das so erhaltene Monoazopigment der FormelThe thus obtained monoazo pigment of the formula
CH,CONHCH, CONH
COCH3 N=N-CH-CONH C=O COCH 3 N = N-CH-CONH C = O
NH'NH '
ergibt beim Einarbeiten in einen Alkyd-Melaminharz- 1400C leuchtendorange Färbungen von hoher Trans-Klarlack und anschließendem Aufziehen des pigmen- parenz, einwandfreier Uberlackierechtheit und vortierten Lacks auf Prüfkarten über schwarzem und wei- 50 züglicher Lichtechtheit, ßem Untergrund nach 30minutigem Einbrennen beiWhen incorporated into an alkyd melamine resin 140 0 C results in bright orange colorations of high trans-clear lacquer and subsequent application of the pigment parenz, impeccable over lacquer fastness and pre-applied lacquer on test cards over black and white light fastness, on the background after 30 minutes of stoving
33,0 g 5-Chlor-2-methyl-4-(2',4'-dichlorbenzoylamino)-anilin werden unter Rühren bei 8O0C in 100 ml 5n-Salzsäure eingetragen. Nach 10 Minuten kühlt man auf Raumtemperatur ab und läßt dann die Suspension über Nacht rühren. Am nächsten Morgen wird mit Eiswasser auf etwa 250 ml verdünnt und bei 5°C mit 20,5 ml 5n-Natriumnitritlösung nach Maßgabe des Verbrauchs diazotiert. Man läßt 30 Minuten nachrühren, zerstört den Nitritüberschuß mit Amidosulfonsäure und klärt.33.0 g of 5-chloro-2-methyl-4- (2 ', 4'-dichlorobenzoylamino) aniline are introduced with stirring at 8O 0 C in 100 ml of 5N hydrochloric acid. After 10 minutes, the mixture is cooled to room temperature and the suspension is then left to stir overnight. The next morning, it is diluted to about 250 ml with ice water and diazotized at 5 ° C. with 20.5 ml of 5N sodium nitrite solution according to consumption. The mixture is left to stir for 30 minutes, the excess nitrite is destroyed with sulfamic acid and clarified.
27,0 g 7 - Chlor - 5 - acetoacetylamino - benzimidazolon werden in 300 ml Wasser angeschlämmt und durch Zugabe von 15 ml 33%iger Natronlauge gelöst. Die geklärte alkalische Lösung tropft man gleichzeitig mit der Diazoniumsalzlösung bei 10 bis 15° C unter Rühren im Laufe einer Stunde zu einer vorgelegten Mischung aus 200 ml Wasser, 25 g Orthophosphorsäure, 30 ml 33%iger Natronlauge und 10 ml einer 10%igen Lösung des Reaktionsproduktes aus 1 Mol Stearylalkohol und 20 Mol Äthylenoxid. Nach beendeter Kupplung wird die Pigmentsuspension 1 Stunde auf 90 bis 95° C erhitzt. Man saugt das Pigment heiß ab, wäscht mit Wasser salzfrei, trocknet bei 60° C und verrührt das gemahlene orangebraune Produkt in 500 ml Eisessig. Die Suspension wird unter Rühren auf 100°C erhitzt, wobei allmählicher Farbumschlag nach Gelb erfolgt. Nach 3stündigem Erhitzen saugt man das gelbe Pigment ab, wäscht27.0 g of 7-chloro-5-acetoacetylamino-benzimidazolone are suspended in 300 ml of water and dissolved by adding 15 ml of 33% sodium hydroxide solution. The clarified alkaline solution is added dropwise at the same time with the diazonium salt solution at 10 to 15 ° C below Stir in the course of an hour to a mixture of 200 ml of water, 25 g of orthophosphoric acid, 30 ml of 33% sodium hydroxide solution and 10 ml of a 10% solution of the reaction product from 1 mol Stearyl alcohol and 20 moles of ethylene oxide. After the coupling has ended, the pigment suspension is 1 hour heated to 90 to 95 ° C. The pigment is filtered off with suction while hot, washed salt-free with water and dried 60 ° C and stir the ground orange-brown product in 500 ml of glacial acetic acid. The suspension will heated with stirring to 100 ° C, gradually increasing The color has changed to yellow. After heating for 3 hours, the yellow pigment is filtered off with suction and washed
mit Methanol säurefrei, trocknet und mahlt. Das so erhaltene Pigment der Formelacid-free with methanol, dries and grinds. The pigment of the formula thus obtained
COCH3
V_N==N_CH—CONHCOCH 3
V_ N == N _CH-CONH
C=OC = O
NH-NH-
ergibt beim Einarbeiten in Polyvinylchlorid, in einen Lack, eine Druckfarbe oder eine Spinnmasse reine gelbe Färbungen von einwandfreier Migrations- und vorzüglicher Lichtechtheit.when incorporated into polyvinyl chloride, varnish, printing ink or spinning material results in pure yellow colorations of perfect migration and excellent lightfastness.
Verwendet man in obigem Beispiel an Stelle von T-Chlor-S-acetoacetylamino-benzimidazolon die äquivalente Menge S-Acetoacetylamino-benzimidazolon, so erhält man ein rotstichiggelbes Pigment, das nach Einarbeiten in eine Druckfarbe, einen Lack, in PolyIf, in the above example, the equivalent is used instead of T-chloro-S-acetoacetylamino-benzimidazolone Amount of S-acetoacetylamino-benzimidazolone, this gives a reddish-tinged yellow pigment which, after being incorporated into a printing ink, a varnish, in poly
vinylchlorid oder in eine Spinnmasse rotstichiggelbevinyl chloride or reddish yellow in a spinning mass
Färbungen mit ähnlich guten EchtheitseigenschaftenDyeings with similarly good fastness properties
ergibt.results.
Die folgende Tabelle enthält eine Anzahl von weiteren verfahrensgemäß verwendbaren Komponen ten sowie die Farbtöne der graphischen Drucke de: daraus in Substanz hergestellten Diazopigmente:The following table contains a number of further components that can be used in accordance with the method th as well as the color tones of the graphic prints de: diazo pigments made from them in substance:
DiazokomponenteDiazo component
3-Amino-acetanilid3-amino-acetanilide
desgl.the same
4-Chlor-3-amino-acetanilid4-chloro-3-amino-acetanilide
desgl.the same
4,6-Dichlor-3-amino-acetanilid desgl.4,6-dichloro-3-amino-acetanilide desgl.
4-Chlor-6-methyl-3-amino-acetaniIid desgl.4-chloro-6-methyl-3-amino-acetaniIid desgl.
4-Brom-6-methyl-3-amino-acetanilid desgl.4-Bromo-6-methyl-3-amino-acetanilide desgl.
6-Methyl-3-amino-acetanilid desgl.6-methyl-3-amino-acetanilide desgl.
4,6-Dimethoxy-3-amino-acetanilid desgl.4,6-dimethoxy-3-amino-acetanilide desgl.
4,6-Dichlor-3-amino-propionanilid desgl.4,6-dichloro-3-aminopropionanilide desgl.
3-Benzoylamino-anilin desgl.3-benzoylamino-aniline like.
3-(2',4'-Dichlorbenzoyl-amino)-anilin desgl.3- (2 ', 4'-dichlorobenzoyl-amino) -aniline desgl.
2-Chlor-5-(2'-chlorbenzoyl-amino)-anilin 2-chloro-5- (2'-chlorobenzoyl-amino) aniline
desgl.the same
2-Chlor-5-(2',4'-dichlorbenzoylamino)-anilin desgl.2-chloro-5- (2 ', 4'-dichlorobenzoylamino) -aniline desgl.
2,4-Dichlor-5-(4'-chlor-3'-methylbenzoy]amino)-anilin desgl.2,4-dichloro-5- (4'-chloro-3'-methylbenzoy] amino) aniline the same
2,4-Dichlor-5-(4'-brombenzoylamino)-anilin desgl.2,4-dichloro-5- (4'-bromobenzoylamino) aniline the same
2-Brom-5-benzoylamino-anilin desgl.2-bromo-5-benzoylamino-aniline desgl.
2-Chlor-4-methyl-5-(2'.5'-dichlorbenzoylamino)-anilin desel.2-chloro-4-methyl-5- (2'.5'-dichlorobenzoylamino) aniline desel.
KupplungskomponenteCoupling component
S-Acetoacetylamino-benzimidazolonS-acetoacetylamino-benzimidazolone
T-Chlor-S-acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone
5-Acetoacetylamino-benzimidazolon5-acetoacetylamino-benzimidazolone
T-Brom-S-acetoacetylamino-benzimidazolonT-bromo-S-acetoacetylamino-benzimidazolone
o-Methyl-S-acetoacetylamino-benzimidazolono-methyl-S-acetoacetylamino-benzimidazolone
T-Methoxy-S-acetoacetylamino-benzimidazolonT-methoxy-S-acetoacetylamino-benzimidazolone
5-Acetoacetylamino-benzimidazolon5-acetoacetylamino-benzimidazolone
o-Chlor-S-acetoacetylamino-benzimidazolono-chloro-S-acetoacetylamino-benzimidazolone
5-Acetoacetylamino-benzimidazolon5-acetoacetylamino-benzimidazolone
ö-Chlor-S-acetoacetylamino-benzimidazolonö-chloro-S-acetoacetylamino-benzimidazolone
5-Acetoacetylamino-benzimidazoIon5-acetoacetylamino-benzimidazoion
T-Chlor-S-acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone
5-Acetoacetylamino-benzimidazolon5-acetoacetylamino-benzimidazolone
o-Brom-S-acetoacetylamino-benzimidazolono-Bromo-S-acetoacetylamino-benzimidazolone
T-Chior-S-acetoacetylamino-benzimidazolonT-Chior-S-acetoacetylamino-benzimidazolone
T-Methyl-S-acetoacetylamino-benzimidazolonT-methyl-S-acetoacetylamino-benzimidazolone
T-Chlor-S-acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone
o-Brom-S-acetoacetylamino-benzimidazolono-Bromo-S-acetoacetylamino-benzimidazolone
T-Äthoxy-S-acetoacetylamino-benzimidazolonT-ethoxy-S-acetoacetylamino-benzimidazolone
o-Methyl-S-acetoacetylamino-benzimidazolono-methyl-S-acetoacetylamino-benzimidazolone
5-Acetoacetylaminobenzimidazolon5-acetoacetylaminobenzimidazolone
o-Chlor-S-acetoacetylamino-benzimidazolon
5-Acetoacetylamino-benzimidazolono-chloro-S-acetoacetylamino-benzimidazolone
5-acetoacetylamino-benzimidazolone
T-Chlor-S-acetoacetylamino-benzimidazolon
5-Acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone
5-acetoacetylamino-benzimidazolone
T-Brom-S-acetoacetylamino-benzimidazolon
T-Chlor-S-acetoacetylamino-benzimidazolonT-bromo-S-acetoacetylamino-benzimidazolone
T-chloro-S-acetoacetylamino-benzimidazolone
y-Methyl-S-acetoacetylamino-benzimidazolon
5-Acetoacetylamino-benzimidazolon
T-Chlor-S-acetoacetylamino-benzimidazolon
5-Acetoacetylamino-benzimidazolony-methyl-S-acetoacetylamino-benzimidazolone
5-acetoacetylamino-benzimidazolone
T-chloro-S-acetoacetylamino-benzimidazolone
5-acetoacetylamino-benzimidazolone
T-Methoxy-S-acetoacetylamino-benzimida^olonT-Methoxy-S-acetoacetylamino-benzimida ^ olon
Farbtonhue
gelbyellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
gelbyellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
gelbyellow
rotstichiggelbreddish yellow
grünstichiggelbgreenish yellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
rotstichiggelbreddish yellow
gelbyellow
gelb
rotstichiggelbyellow
reddish yellow
gelb
rotstichiggelbyellow
reddish yellow
gelb
gelbyellow
yellow
gelbyellow
gelbyellow
grünstichiggelbgreenish yellow
rotstichiggelbreddish yellow
rr>l«tii-liioop1hrr> l «tii-liioop1h
1111
Fortsetzungcontinuation
DiazokomponenteDiazo component
2-Methyl-5-(2',4'-dichlor-benzoylamino)-anilin desgl.2-methyl-5- (2 ', 4'-dichloro-benzoylamino) -aniline desgl.
4-Methyl-5-(4'-chlor-2'-methoxybenzoylamino-anilin desgl.4-methyl-5- (4'-chloro-2'-methoxybenzoylamino-aniline desgl.
2-Methoxy-5-(4'-chlor-3'-methylbenzoylarnino)-anilin desgl.2-methoxy-5- (4'-chloro-3'-methylbenzoylarnino) -aniline desgl.
4-Amino-acetanilid desgl.4-amino-acetanilide desgl.
2-Chlor-4-aminoacetanilid desgl.2-chloro-4-aminoacetanilide desgl.
3-Chlor-4-amino-acetanilid desgl.3-chloro-4-amino-acetanilide desgl.
desgl.the same
2,5-Dichlor-4-amino-acetanilid desgl.2,5-dichloro-4-amino-acetanilide desgl.
2-Chlor-5-methyl-4-amino-acetanilid desgl.2-chloro-5-methyl-4-amino-acetanilide the same
desgl.the same
2-Methoxy-5-methyl-4-aminoacetanilid desgl.2-methoxy-5-methyl-4-aminoacetanilide desgl.
2,5-Dimethoxy-4-amino-acetanilid desgl.2,5-dimethoxy-4-amino-acetanilide desgl.
2,5-Dichlor-4-aminopropionanilid desgl.2,5-dichloro-4-aminopropionanilide desgl.
4-Benzoylamino-anilin desgl.4-benzoylamino-aniline like.
4-(4'-Chlorbenzoylamino)-anilin desgl.4- (4'-chlorobenzoylamino) aniline desgl.
4-(2',4'-Ddchlorbenzoyl-amino)-anilin desgl.4- (2 ', 4'-D-chlorobenzoyl-amino) -aniline desgl.
3-Chlor-4-(4'-chlor-benzoylamino)-anilin desgl.3-chloro-4- (4'-chloro-benzoylamino) -aniline desgl.
3-Chlor-4-(4'-chlorbenzoylamino)-fcnilin 3-Chlor-4-(2',4'-dichlorbenzoylkmino)-anilin desgl.3-chloro-4- (4'-chlorobenzoylamino) -fcniline 3-chloro-4- (2 ', 4'-dichlorobenzoylkmino) -aniline the same
3-Chlor-4-(4'-chlor-3'-methylfeenzoylarnino)-amlin desgl.3-chloro-4- (4'-chloro-3'-methylfeenzoylarnino) amline the same
2,5-Dichlor-4-{4'-chlor-2'-methoxybenzoylarninoj-anilin desgl.2,5-dichloro-4- {4'-chloro-2'-methoxybenzoylarninoj-aniline the same
3-Brom-4-(4'-chlorbenzoylamino)-anilin desgl.3-Bromo-4- (4'-chlorobenzoylamino) aniline the same
2-Chlor-5-methyl-4-(4'-chlorbenzoylarnino)-anilin desgl.2-chloro-5-methyl-4- (4'-chlorobenzoylamino) aniline the same
1212th
KupplungskomponenteCoupling component
FarbionColor ion
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
o-Methyl-S-acetoacetylamino-benzimidazolon rotstichiggelbo-Methyl-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon rotstichiggel bS-acetoacetylamino-benzimidazolone reddish yellow b
ö-Chloi-S-acetoacetylamino-benzimidazolon gelbö-Chloi-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
T-Chlor-S-acetoacetylamino-benzimidazolon grünstichiggelbT-chloro-S-acetoacetylamino-benzimidazolone greenish yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
T-Chlor-S-acetoacetylamino-benzimidazolon gelbT-chloro-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
V-Methyl-S-acetoacetylamino-benzimidazolon gelbV-methyl-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
o-Chlor-S-acetoacetylamino-benzimidazolon grünstichiggelbo-chloro-S-acetoacetylamino-benzimidazolone greenish yellow
T-Methoxy-S-acetoacetylamino-benzimidazolon rotstichiggelbT-Methoxy-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Chlor-S-acetylamino-benzimidazolon gelbT-chloro-S-acetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
T-Chlor-S-acetoacetylamino-benzimidazolon grünstichiggelbT-chloro-S-acetoacetylamino-benzimidazolone greenish yellow
V-Methyl-S-acetoacetylamino-benzimidazolon gelbV-methyl-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
o-Methyl-S-acetoacetylamino-benzimidazolon rotstichiggelbo-Methyl-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon orangeS-acetoacetylamino-benzimidazolone orange
V-Brom-S-acetoacetylamino-benzimidazolon rotstichiggelbV-bromo-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
o-Chlor-S-acetoacetylamino-benzimidazolon gelbo-chloro-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
o-Brom-S-acetoacetylamino-benzimidazolon gelbo-Bromo-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Chlor-S-acetoacetylamino-benzimidazolon gelbT-chloro-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Äthoxy-S-acetoacetylamino-benzimidazolon rotstichiggelbT-Ethoxy-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Chlor-S-acetoacetylamino-benzimidazolon gelbT-chloro-S-acetoacetylamino-benzimidazolone yellow
o-Methyl-S-acetoacetylamino-benzimidazolon gelbo-Methyl-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
o-Brom-S-acetoacetylamino-benzimidazolon gelbo-Bromo-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Methoxy-S-acetoacetylamino-benzimidazolon rotstichiggelbT-Methoxy-S-acetoacetylamino-benzimidazolone reddish yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
T-Chlor-S-acetoacetylamino-benzimidazolon gelbT-chloro-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon gelbS-acetoacetylamino-benzimidazolone yellow
ö-Methyl-S-acetoacetylamino-benzimidazolon gelbö-Methyl-S-acetoacetylamino-benzimidazolone yellow
S-Acetoacetylamino-benzimidazolon rotstichiggelbS-acetoacetylamino-benzimidazolone reddish yellow
V-Brom-S-acetoacetylamino-benzimidazolon gelbV-bromo-S-acetoacetylamino-benzimidazolone yellow
1313th
Fortsetzungcontinuation
DiazokomponenteDiazo component
2-Chlor-5-methyI-4-(2\4'-dichlorbenzoylamino)-anilin desgl.2-chloro-5-methyl-4- (2 \ 4'-dichlorobenzoylamino) aniline the same
5-Chlor-2-methyl-4-(4'-chlorbenzoylamino)-anilin desgl.5-chloro-2-methyl-4- (4'-chlorobenzoylamino) aniline desgl.
5-Chlor-2-methyl-4-(4'-brombenzoylamino)-anilin desgl.5-chloro-2-methyl-4- (4'-bromobenzoylamino) aniline the same
2-Methoxy-4-(4'-brombenzoylamino)-anilin desgl.2-methoxy-4- (4'-bromobenzoylamino) aniline the same.
4-Äthyl-3-amino-acetanilid «♦-Äthoxy-S-amino-acetanilid 2,5-Diäthoxy-4-amino-acetanilid 14 4-ethyl-3-amino-acetanilide «♦ -ethoxy-S-amino-acetanilide 2,5-diethoxy-4-amino-acetanilide 14
KupplungskomponenteCoupling component
T-Chlor-S-acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone
o-Methyl-S-acetoacetylamino-benzimidazolon S-Acetoacetylamino-benzimidazolono-methyl-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone
T-Chlor-S-acetoacetylamino-benzimidazolon S-Acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone
o-Chlor-S-acetoacetylamino-benzimidazolon S-Acetoacetylamino-benzimidazolono-chloro-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone
T-Chlor-S-acetoacetylamino-benzimidazolon S-Acetoacetylamino-benzimidazoIon S-Acetoacetylamino-benzimidazolon S-Acetoacetylamino-benzimidazolonT-chloro-S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazoIon S-acetoacetylamino-benzimidazolone S-acetoacetylamino-benzimidazolone
Farbtonhue
gelbyellow
gelb gelbyellow yellow
gelb gelbyellow yellow
gelb rolstichiggelbyellow tinged yellow
gelbyellow
gelbyellow
rotstichiggelbreddish yellow
orangeorange
Claims (1)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732338973 DE2338973C3 (en) | 1973-08-01 | Monoazo pigments, process for their production and their use | |
| IN1613/CAL/1974A IN140885B (en) | 1973-08-01 | 1974-07-19 | |
| NL7410102A NL7410102A (en) | 1973-08-01 | 1974-07-26 | PROCEDURE FOR PREPARING NEW MONOAZ PIGMENTS. |
| CH1042874A CH611641A5 (en) | 1973-08-01 | 1974-07-29 | Process for preparing novel monoazo compounds |
| IT25733/74A IT1017726B (en) | 1973-08-01 | 1974-07-30 | MONOAZOPIGMENTS AND PROCESS FOR THEIR PREPARATION |
| GB3358274A GB1473556A (en) | 1973-08-01 | 1974-07-30 | Monoazo pigments and process for preparing them |
| AR254952A AR203117A1 (en) | 1973-08-01 | 1974-07-30 | NEW MONOAZOIC PIGMENTS OF ACILAMINOPHENIL-AZOACETOACETILAMINO-BENZYMIDAZOLONE, PROCEDURE FOR THEIR PREPARATION AND COMPOSITIONS THAT CONTAIN THEM |
| CA206,015A CA1034117A (en) | 1973-08-01 | 1974-07-31 | Monoazo pigments and process for preparing them |
| AU71891/74A AU482291B2 (en) | 1973-08-01 | 1974-07-31 | New monoazo pigments and process for their preparation |
| DK410074A DK136079C (en) | 1973-08-01 | 1974-07-31 | MONOAZO COMPOUNDS FOR USE AS PIGMENT |
| JP49087091A JPS5853024B2 (en) | 1973-08-01 | 1974-07-31 | Shinkimono Azoganriyouno Seihou |
| FR7426747A FR2239495B1 (en) | 1973-08-01 | 1974-08-01 | |
| BE147219A BE818406A (en) | 1973-08-01 | 1974-08-01 | MONOAZOIC PIGMENTS AND THEIR PREPARATION |
| BR6330/74A BR7406330D0 (en) | 1973-08-01 | 1974-08-01 | MONOAZOUS PIGMENTS PROCESS FOR THE PREPARATION OF THE SAME AND ITS APPLICATIONS |
| US05/667,432 US4080321A (en) | 1973-08-01 | 1976-03-16 | Monoazo pigments from diazotized acylamino-anilines and acetoacetylamino benzimidazolones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732338973 DE2338973C3 (en) | 1973-08-01 | Monoazo pigments, process for their production and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2338973A1 DE2338973A1 (en) | 1975-03-06 |
| DE2338973B2 true DE2338973B2 (en) | 1975-06-19 |
| DE2338973C3 DE2338973C3 (en) | 1976-02-05 |
Family
ID=
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2800765A1 (en) * | 1977-01-11 | 1978-07-13 | Ciba Geigy Ag | NEW MONOAZO PIGMENTS AND PROCESS FOR THEIR PRODUCTION |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2800765A1 (en) * | 1977-01-11 | 1978-07-13 | Ciba Geigy Ag | NEW MONOAZO PIGMENTS AND PROCESS FOR THEIR PRODUCTION |
Also Published As
| Publication number | Publication date |
|---|---|
| DK410074A (en) | 1975-04-01 |
| DK136079C (en) | 1978-01-16 |
| DE2338973A1 (en) | 1975-03-06 |
| NL7410102A (en) | 1975-02-04 |
| DK136079B (en) | 1977-08-08 |
| FR2239495A1 (en) | 1975-02-28 |
| CA1034117A (en) | 1978-07-04 |
| GB1473556A (en) | 1977-05-18 |
| BR7406330D0 (en) | 1975-05-20 |
| BE818406A (en) | 1975-02-03 |
| IT1017726B (en) | 1977-08-10 |
| AR203117A1 (en) | 1975-08-14 |
| AU7189174A (en) | 1976-02-05 |
| CH611641A5 (en) | 1979-06-15 |
| JPS5071721A (en) | 1975-06-13 |
| JPS5853024B2 (en) | 1983-11-26 |
| FR2239495B1 (en) | 1978-11-24 |
| IN140885B (en) | 1977-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1544460B2 (en) | Bfs (acetoacet) arykliamide disazo pigment dyes | |
| DE1808015A1 (en) | New water-insoluble nonoazo dyes and processes for their preparation | |
| DE2200112C3 (en) | Carbostyril monoazo compounds, process for their preparation and their use as pigments | |
| DE2935974A1 (en) | DISAZO CONNECTIONS, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
| DE2329781C2 (en) | Benzoxazinedione azo pigments, process for their preparation and their use as colorants | |
| EP0010273A1 (en) | Monoazo-compounds of the acetoacetylaminobenzimidazolone series, their preparation and use | |
| DE1939466C3 (en) | Monoazo compounds, process for their preparation and their use as colorants | |
| DE2144907C3 (en) | New water-insoluble mono- and disazo compounds, processes for their preparation and their use as pigments | |
| DE2338973C3 (en) | Monoazo pigments, process for their production and their use | |
| DE2336915A1 (en) | NEW DISAZOPIGMENTS AND METHODS OF MANUFACTURING AND USE | |
| DE2130040C3 (en) | Water-insoluble monoazo compounds, process for their preparation and their use | |
| DE2338973B2 (en) | Monoazo pigments, process for their production and their use | |
| DE2651919A1 (en) | DISAZO COMPOUNDS, PROCEDURES FOR THEIR MANUFACTURING AND THEIR USE AS A COLORANT | |
| DE2800765A1 (en) | NEW MONOAZO PIGMENTS AND PROCESS FOR THEIR PRODUCTION | |
| DE2843873A1 (en) | AZO CONNECTIONS | |
| DE2302522C3 (en) | Disazoplgmente, process for their preparation and their use for dyeing | |
| DE2043483C3 (en) | Water-insoluble monoazo dyes, process for their preparation and use | |
| DE2905937A1 (en) | Methyl carbostyril azo phenyl acetamido pyrazolone cpds. - used as pigments and dyestuffs, in ink,, paint, plastics etc. and used for printing textiles and paper | |
| DE2328678C3 (en) | New disazo pigments, processes for their production and their uses | |
| DE1795052C3 (en) | Water-insoluble monoazo compounds, process for their preparation and their use as pigments | |
| EP0010272A1 (en) | Azo-compounds, process for their preparation and their use | |
| DE1208435B (en) | Process for the preparation of water-insoluble monoazo dyes | |
| DE2204769A1 (en) | HYDRO-INSOLUBLE DISAZO DYES | |
| EP0055850B1 (en) | Disazo compounds, methods for their preparation and their use | |
| DE1644231C (en) | Water-insoluble monoazo dye and its use for inks and printing |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |