EP0000737B1 - Pigments monoazoiques de la série acétoacétylaminobenzimidazolone, leur préparation et utilisation pour la pigmentation de matières organiques macromoléculaires - Google Patents

Pigments monoazoiques de la série acétoacétylaminobenzimidazolone, leur préparation et utilisation pour la pigmentation de matières organiques macromoléculaires Download PDF

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Publication number
EP0000737B1
EP0000737B1 EP19780100516 EP78100516A EP0000737B1 EP 0000737 B1 EP0000737 B1 EP 0000737B1 EP 19780100516 EP19780100516 EP 19780100516 EP 78100516 A EP78100516 A EP 78100516A EP 0000737 B1 EP0000737 B1 EP 0000737B1
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EP
European Patent Office
Prior art keywords
formula
amino
methyl
azo pigments
hydrogen
Prior art date
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Expired
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EP19780100516
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German (de)
English (en)
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EP0000737A1 (fr
Inventor
Rolf Müller
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Novartis AG
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Ciba Geigy AG
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Publication date
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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
    • C09B29/32—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
    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds

Definitions

  • the invention relates to new monoazo pigments based on heterocyclic diazo components coupled with acetomethylaminobenzimidazolone.
  • French patent publication 2,128,514 already describes monoazo pigments which are prepared by coupling the diazotized amines, in particular benzoxazolones and benzimidazolones, with acetoacetylamino-benzimidazolones which are substituted on an nitrogen atom by an alkyl, cycloalkyl or aryl group.
  • the azo pigments obtained have low light fastness, so that they are not very suitable for pigmenting high molecular weight organic material.
  • Acetoacetylamino-benzimidazolones with unsubstituted nitrogen atoms as coupling components are already known from French patent publications 2,167,629 and 2,233,373, but in combination with other heterocyclic diazo components which differ structurally from the diazo components of the new monoazo pigments.
  • Preferred compounds of the formula (1) are those in which Q is a group of the formula -CONH and Z is an O atom or a group of the formula -CONH and Z is a 0 atom or a group of the formulas -NH- or -NHCO - mean.
  • X is preferably hydrogen, chlorine, methyl or methoxy and Y is hydrogen, chlorine, methyl, methoxy or ethoxy.
  • the acetoacetic arylides to be used as coupling component are obtained, for example, by addition of diketene to the corresponding aminobenzimidazolones.
  • the coupling is expediently carried out by gradually combining the aqueous alkaline solution of the coupling component with the acidic solution of the diazonium salt, preferably at a pH of 4 to 6.
  • the pH is advantageously adjusted by adding a buffer.
  • a buffer come e.g. the salts, in particular alkali salts, of formic acid, phosphoric acid or in particular acetic acid.
  • the alkaline solution of the coupling component suitably contains a wetting, dispersing or emulsifying agent, for example an aralkyl sulfonate, such as dodecylbenzenesulfonate or the sodium salt of 1,1'-dinaphthylmethanesulfonic acid, polycondensation products of alkylene oxides, such as the action product of ethylene oxide on p-tert-octylphenol also alkyl esters of sulforicinoleates, for example n-butylsulforicinoleate.
  • aralkyl sulfonate such as dodecylbenzenesulfonate or the sodium salt of 1,1'-dinaphthylmethanesul
  • the dispersion of the coupling component can also advantageously contain protective colloids, for example methyl cellulose or smaller amounts of inert organic solvents which are sparingly soluble or insoluble in water, for example halogenated or nitrated aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzenes or nitrobenzene, and aliphatic halogenated hydrocarbons such as e.g. Carbon tetrachloride or trichlorethylene, and also water-miscible organic solvents, such as acetone, methyl ethyl ketone, methanol, ethanol or isopropanol, especially dimethylformamide.
  • protective colloids for example methyl cellulose or smaller amounts of inert organic solvents which are sparingly soluble or insoluble in water, for example halogenated or nitrated aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzen
  • the coupling can also be carried out advantageously in such a way that an acidic solution of the diazonium salt with an alkaline solution of the coupling component in a mixing nozzle continuously combined, with an immediate coupling of the components.
  • the resulting dye dispersion is continuously removed from the mixing nozzle and the dye is separated off by filtration.
  • the coupling can also be carried out by suspending the amine with the coupling component in a molar ratio of 1: 1 in an organic solvent and with a diazotizing agent, in particular an ester of nitrous acid, such as methyl, ethyl, butyl or amyl or octyl nitrite.
  • a diazotizing agent in particular an ester of nitrous acid, such as methyl, ethyl, butyl or amyl or octyl nitrite.
  • the pigments obtained can be isolated from the reaction mixtures by filtration.
  • the pigments obtained are obtained in excellent purity.
  • the pigments obtained generally have a good texture and can often be used as raw products. If necessary or desired, the raw products can be converted into a finely dispersed form by grinding or kneading. It is useful to use grinding aids such as inorganic and / or organic salts in the presence or absence of organic solvents. After grinding, auxiliary agents are removed as usual, soluble inorganic salts e.g. with water and water-insoluble organic auxiliaries, for example by steam distillation. An improvement in the properties can often also be achieved by treating the raw pigments with organic solvents, preferably those which boil above 100 ° C.
  • benzenes substituted by halogen atoms, alkyl or nitro groups such as xylenes, chlorobenzene, o-dichlorobenzene or nitrobenzene, and pyridine bases, such as pyridine, picoline or quinoline, and also ketones, such as cyclohexanone, ethers, such as ethylene glycol monomethyl or monoethyl ether, amides , such as dimethylformamide or N-methyl-pyrrolidone, and also dimethyl sulfoxide, sulfolane or water alone, optionally under pressure.
  • the aftertreatment can also be carried out in water in the presence of organic solvents and / or with the addition of surface-active substances.
  • the aftertreatment is preferably carried out by heating the pigment in the solvent to 100 to 150 ° C., which in many cases leads to coarsening of the grain, which has a favorable effect on the fastness to light and migration of the pigments obtained.
  • the new dyes are valuable, mostly strong-colored pigments with good migration, light, weather and heat fastness. They can be used individually or in mixtures in finely divided form to pigment high-molecular organic material, e.g. of cellulose ethers and esters, polyamides, polyurethanes, polyesters, acetyl cellulose, nitrocellulose, natural resins or synthetic resins, such as polymerization or condensation resins, e.g.
  • Aminoplasts especially urea and melamine-formaldehyde resins, alkyd resins, phenoplasts, polycarbonates, polyolefins such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, rubber, casein, silicone and silicone resins.
  • 6-Amino-5-methylbenzoxazolone is prepared by known processes, but preferably analogously to the preparation of benzimidazolones, as described in DE-OS 2 725 957.
  • the fastness and the texture of the pigment are further improved by heating the crude pigment in water in the presence of 1% of a condensation product of 1 mol of oleyl alcohol and 20 mol of ethylene oxide at 150 ° C. under pressure for 6 hours.
  • a pigment is obtained which colors PVC in a reddish yellow shade with very good fastness to migration, light and weather.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Coloring (AREA)

Claims (11)

1. Pigments azoïques répondant à la formule
Figure imgb0040
dans laquelle
X et Y représentent chacun un atome d'hydrogène ou d'halogène ou un radical alkyle ou alcoxy contenant de 1 à 4 atomes de carbone,
Q représente un groupe -CONH- ou -NHCO- et
Z représente un atome d'oxygène ou un groupe répondans à l'une des formules -NR-, -NHCO-, -CONH-, -CH=N- ou
Figure imgb0041
dans lesquelles R
représente un atome d'hydrogène, un radical alkyle en Cl-C4 ou un radical phényle éventuellement porteur d'un halogène, d'un alkyle ou d'un alcoxy en C1-C4 et V représente un atome d'hydrogène ou d'halogène, un alkyle ou un alcoxy en C1-C5, et dans laquelle le groupe azoïque est relié au radical phényle
A ou au radical phényle B.
2. Pigments azoïques selon la revendication 1 qui répondent à la formule
Figure imgb0042
dans laquelle Z représente un atome d'oxygène ou un groupe -NH- ou -NHCO-.
3. Pigments azoïques selon la revendication 2, caractérisés en ce que, dans la formule représentée, X représente un atome d'hydrogène ou de chlore ou un radical méthyle ou méthoxy et Y représente un atome d'hydrogène ou de chlore ou un radical méthyle, méthoxy ou éthoxy.
4. Pigments azoïques selon la revendication 3 qui répondent à la formule:
Figure imgb0043
5. Pigments azoïques selon la revendication 3 qui répondent à la formule:
Figure imgb0044
6. Pigments azoïques selon la revendication 3 qui répondent à la formule:
Figure imgb0045
7. Pigments azoïques selon la revendication 1, caractérisés en ce qu'ils répondent à la formule:
Figure imgb0046
8. Pigments azoïques selon la revendication 1, caractérisés en ce qu'ils répondent à la formule:
Figure imgb0047
9. Procédé de préparation des pigments azoïques selon la revendication 1, caractérisé en ce qu'on copule le diazoïque d'une amine de formule
Figure imgb0048
avec un acéto-acétylarylide de formule
Figure imgb0049
10. Procédé selon la revendication 9, caractérisé en ce qu'on utilise un copulant répondant à la formule
Figure imgb0050
dans laquelle X représente un atome d'hydrogène ou de chlore ou un radical méthyle ou méthoxy.
11. Procédé pour pigmenter des matières organiques macromoléculaires, procédé caractérisé en ce qu'on utilise un pigment azoïque selon l'une quelconque des revendications 1 à 8.
EP19780100516 1977-08-04 1978-07-27 Pigments monoazoiques de la série acétoacétylaminobenzimidazolone, leur préparation et utilisation pour la pigmentation de matières organiques macromoléculaires Expired EP0000737B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH958177 1977-08-04
CH9581/77 1977-08-04

Publications (2)

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EP0000737A1 EP0000737A1 (fr) 1979-02-21
EP0000737B1 true EP0000737B1 (fr) 1981-04-29

Family

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Family Applications (1)

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EP19780100516 Expired EP0000737B1 (fr) 1977-08-04 1978-07-27 Pigments monoazoiques de la série acétoacétylaminobenzimidazolone, leur préparation et utilisation pour la pigmentation de matières organiques macromoléculaires

Country Status (6)

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EP (1) EP0000737B1 (fr)
JP (1) JPS5429334A (fr)
BR (1) BR7804978A (fr)
CA (1) CA1087173A (fr)
DE (1) DE2860649D1 (fr)
DK (1) DK344678A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2847285A1 (de) * 1978-10-31 1980-05-14 Hoechst Ag Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE4007535A1 (de) * 1990-03-09 1991-09-12 Hoechst Ag Wasserunloesliche azofarbmittel, ihre herstellung und verwendung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH552034A (de) * 1971-03-03 1974-07-31 Ciba Geigy Ag Verfahren zur herstellung von neuen azopigmenten.
BE793635A (fr) * 1972-01-03 1973-07-03 Hoechst Ag Colorants azoiques solides a la chaleur
DE2329781C2 (de) * 1973-06-12 1986-06-05 Hoechst Ag, 6230 Frankfurt Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel
CH611642A5 (fr) * 1976-11-09 1979-06-15 Ciba Geigy Ag

Also Published As

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DE2860649D1 (en) 1981-08-06
JPS6143387B2 (fr) 1986-09-27
EP0000737A1 (fr) 1979-02-21
JPS5429334A (en) 1979-03-05
CA1087173A (fr) 1980-10-07
BR7804978A (pt) 1979-04-10
DK344678A (da) 1979-02-05

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