USRE25857E - Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs - Google Patents

Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs Download PDF

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USRE25857E
USRE25857E US25857DE USRE25857E US RE25857 E USRE25857 E US RE25857E US 25857D E US25857D E US 25857DE US RE25857 E USRE25857 E US RE25857E
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C08K5/3447—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • 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

Definitions

  • the present invention relates to novel water-insoluble azo-dyestufls and to a process for preparing them; more particularly it relates to dyestuffs of the following general formula wherein X represents a halogen atom, a nitro, methyl, methoxy or trifluoromethyl group, the benzene nucleus A may be substituted by further groups which do not impart solubility in water and the benzene nucleus B may be substituted by methyl groups, methoxy groups or halogen atoms, by coupling the diazo compounds of amines of the benzene series which contain in orthoposition to the amino group a halogen atom or :1 nitro, methyl, methoxy or trifluoromethyl group and which may be substituted by further groups which do not impart solubility in water, with the acetoacetyl compounds of S-amino-benzimidazolones which may be substituted in the benzene nucleus of the benzimidazol
  • amines of the benzene series having the above-mentioned composition such as for example 1 amino 2 nitrobenzene, l amino-Z-chlorobenzene, 1 amino-Z-methylbenzene, 1 amino-2-rnethoxybenzene, l-amino-Z,S-dichlorobenzene, 1arnino-2-nitro-4-methoxybenzene, 1 amino-2-nitro-4-chlorobenzene, l amino-2- nitro 4 methylbenzene, l-amino 2 chloro-S-trifluoromethylbenzene, l-amino-Z-chlorobenzene 5 carboxylic acid amide, l-amino-2-chloro-4-methylbenzene, l-arnino- 2-ehloro-3-methylbenzene, 1-amino-2-bromo-4-nitrobenzene, 1 amino-2-methyl-6-chlorobenzene
  • acetoacetyl compound of the S-aminobenzimidazolone there may be used the corresponding derivatives which may be substituted in the benzene nucleus of the benzimidazolone radical by methyl groups or methoxy groups or halogen atoms, such as for example 5 acetoacetylaminoJ-chloro benzimidazolone, 5 acetoacetylamino-7-bromo-benzimidazolone, 5 acetoacetylamino-G-chloro benzimidazolone, 5 acetoacetylamino-6-methyl benzimidazolone, 5-acetoacetylamino-7- methyl-benzimidazolone, S-acetoacetylamino-7-methoxybenzimidazolone or 5 acetoacetylamino-4,7 dimethylbenzimidazolone.
  • the preparation of the pigments can be carried out in such a manner that the solution of the diazo compound is combined with the coupling component present in a weakly acid medium in a finely dispersed form or that the alkaline solution of the coupling component is added to the solution of the diazo component first introduced into the reaction vessel and adjusted to a pH-value of 5 to 6 by the addition of sodium acetate.
  • a further possibility for carrying out the coupling is to add the solutions of the diazo and the coupling component simultancously to a buffer mixture of sodium acetate and acetic acid. With all these working methods the presence of cationic, anionic or non-ionic surface-active compounds may be advantageous.
  • the dyestuffs obtained often possess a hard grain and have to be subjected to an after-treatment in order to obtain the full tinctorial strength.
  • an after-treatment it is expedient to use pyridine, dimethyl formamide, quinoline or N-methylacetamide at an elevated temperature.
  • the dyestuffs may also be heated under pressure in the form of their aqueous pastes to temperatures above (1., preferably to C. to C., the addition of alcohols or other organic solvents facilitating the transformation of the dyestutf into a form exhibiting a high tinctorial strength. This transformation is sometimes successfully carried out by simply heating the dyestults in aqueous alcohols.
  • novel pigments are suitable for the preparation of printing colors and for the preparation of color lakes. They can also be used for dyeing rubber and plastics, especially polyvinylchloride.
  • the novel pigments are distinguished in addition to a very good fastness to light by an improved fastness to solvents. That is to say the novel pigments possess all the properties imparted by the improved fastness to solvents, such as fastness to oil, to overspraying, to overvarnishing, to blooming and to bleeding.
  • EXAMPLE 1 86.5 parts of l-amino 2 nitro 4 chlorobenzene are stirred for several hours, advantageously over night, with 400 parts by volume of 5 N-hydrochlori-c acid. Then 200 parts of ice are added to the suspension and the mixture is diazotized by introducing under its surface within about 2 hours 100 parts by volume of a N-sodium nitrite solution, while vigorously stirring. By the occasional addition of ice the temperature is maintained below 5 C. When the diazotization is complete the diazo solution is clarified by adding a small quantity of kieselguhr and, a minor excess of nitrous acid is removed by means of a small amount of amido sullonic acid.
  • the coupling is immediately complete.
  • the mixture is after-stirred for 2 hours, the black brown dyestutt is filtered off with suction and washed thoroughly with water.
  • the thoroughly expressed filter residue is stirred with 1000 parts by volume of pyridine to yield a homogeneous paste.
  • the mixture is heated at the boil for 1 hour under refiux, while stirring, whereby the dark brown dyestuff is transformed into an orange red product.
  • the pyridine is removed by distillation with steam, the dyestutt is filtered off with suction and dried at 60 C.
  • EXAMPLE 2 with 125 parts by volume of 2 N-acetic acid and with 600 L parts by volume of alcohol to yield a homogeneous paste. Then the mixture is heated at the boil for 7 to 8 hours while stirring and cooling under reflux, whereby the brown dyestuff is gradually transformed into an orange red product; the mixture is diluted with hot water to double U its volume and subjected for 1 hour to a distillation with steam. The dyestuif is filtered otf with suction and dried at 60 C.
  • EXAMPLE 3 17.5 parts of l-amino-2-nitro-4-chlorobenzene are diazotized as described in Example 1 and coupled at 20 C. and at a pH-value of 4 with the acetic suspension of 24 parts of 5acetoacetylamino-benzimidazolone. The mixture is after-stirred for 2 hours, the black brown dyestuff is filtered oti with suction, thoroughly washed with water and dried at 60 C. 40 parts of a dark, almost black dyestuff possessing a low tinctorial strength and a hard grain are obtained.
  • the finely pulverized dyestufl is then stirred for 4 hours at normal temperature with 400 parts by volume of pyridine, whereby the initially dilute suspension gradually thickens.
  • the dyestulf is filtered ofi with suction, Washed first with a small amount of pyridine, then thoroughly washed with water and dried at 60 C.
  • EXAMPLE 4 17 parts of 3-amino-4-chloro-benzamide are dissolved in 200 parts by volume of 2 N-hydrochloric acid. The solution is cooled to 5 C. by the addition of ice and diazotized with 50 parts by volume of 2 N-sodium nitrite solution. The diazo solution is made up to 500 parts by volume by adding ice water.
  • S-acetoacetylamino-benzimidazolone are dissolved at normal temperature in 150 parts by volume of 2 N-sodiurn hydroxide solution.
  • the solution is made up to 500 parts by volume by adding water.
  • Both solutions are introduced simultaneously, while vigorously stirring, into a butler solution of a pH-value of 5 containing 50 parts by volume of 2 N-acetic acid, 200 parts by volume of 2 Nsodium acetate solution and 200 parts by volume of water.
  • a butler solution of a pH-value of 5 containing 50 parts by volume of 2 N-acetic acid, 200 parts by volume of 2 Nsodium acetate solution and 200 parts by volume of water.
  • the coupling is also complete.
  • the mixture is heated to 90 C. by introducing steam, the yellow dyestufi is filtered oil with suction and washed thoroughly with water.
  • the thoroughly expressed moist dyestuff is then stirred with 200 parts by volume of pyridine to yield a homogenous paste which, while stirring, is heated at the boil for 1 hour under reflux. Subsequently the pyridine is distilled oil with steam. The dyestuff is filtered off with suction and dried at 60 C. parts of a yellow pigment possessing a soft grain and a high tinctorial strength and a very good fastness to solvents and to light are obtained.
  • EXAMPLE 5 14.2 parts of 1-amino-2-methyl-4-chlorobenzene are diazotized at temperatures below 10 C. in known manner with 200 parts by volume of 2 N-hydrochloric acid and parts by volume of 2 N-sodium nitrite solution. The diazo solution which, if desired, has been clarified and freed from the nitrous acid in excess is made up to 500 parts by volume by adding ice water.
  • Both solutions are introduced simultaneously, while quickly stirring, into a buffer solution of 50 parts by volume of 2 N-acetic acid, 200 parts by volume of 2 N-sodium nitrite solution and 100 parts by volume of water.
  • the coupling is soon complete.
  • the dyestulf is filtered off with suction, thoroughly washed with water and dried at C.
  • 42 parts of a yellow pigment possessing a low tinctorial strength which is finely pulverized and stirred at normal temperature for 2 hours with 350 parts by volume of pyridine, whereby the initially dilute suspension thickens considerably.
  • the mixture is then heated for 1 hour to 50 C., diluted with the same volume of warm water, the dyestulf is filtered off with suction, washed with hot water and dried at 60 C.
  • EXAMPLE 6 15 parts of 3-amino-4-methyl-benzamide are diazotized in known manner at temperatures below 10 C. with 200 parts by volume of 2 N-hydrochloric acid and 50 parts by volume of a 2 N-sodium nitrite solution. 200 parts by volume of 2 N-sodium acetate solution are added to the diazo solution.
  • the water insoluble monoazo-dyestulis having the formula wherein X represents a member of the group consisting of chlorine, methyl, methoxy, nitro and trifluoromelhyl, R represents a member of the group consisting of hydrogen, chlorine, methyl, methoxy, nitro, carboxylic acid amide, carboxylic acid-N-methyl amide, carboxylic acid- N-phenylamide and trifiuoromethyl, and R represents a member of the group consisting of hydrogen, chlorine, bromine, methyl and methoxy.
  • the water-insoluble monoazo-dyestutt having the formula C113 No; NII-C o l O l 3.
  • the water-insoluble monoazo-dyestuff having the formula OH: NO; NHCO 4.
  • the water-insoluble monoazo-dyestuff having the formula Nll CO 5.
  • the water-insoluble monoazo-dyestutf having the formula 6.
  • the water-insoluble monoazo-dyestutf having the formula Ll. H III II 0 No references cited.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US25857D 1961-09-14 Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs Expired USRE25857E (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF34924A DE1227585B (de) 1961-09-14 1961-09-14 Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen

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USRE25857E true USRE25857E (en) 1965-09-14

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US (1) USRE25857E (en, 2012)
BE (1) BE622476A (en, 2012)
CH (1) CH420422A (en, 2012)
DE (1) DE1227585B (en, 2012)
DK (1) DK103085C (en, 2012)
GB (1) GB1008166A (en, 2012)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080321A (en) 1973-08-01 1978-03-21 Hoechst Aktiengesellschaft Monoazo pigments from diazotized acylamino-anilines and acetoacetylamino benzimidazolones

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL176473C (nl) * 1973-01-19 1985-04-16 Hoechst Ag Werkwijze voor het nabehandelen van een azopigment, alsmede gevormde voortbrengselen bekleed met een preparaat dat een aldus nabehandeld azopigment bevat.
DE2518922C2 (de) * 1975-04-29 1982-08-19 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2)
CH627200A5 (en) * 1977-01-11 1981-12-31 Ciba Geigy Ag Process for preparing new monoazo pigments and use thereof for pigmenting macromolecular organic material
DE2947441A1 (de) * 1979-11-24 1981-06-04 Hoechst Ag, 6000 Frankfurt Azoverbindungen, verfahren zur ihrer herstellung und ihre verwendung
CN104513494A (zh) * 2014-12-25 2015-04-15 上虞舜联化工有限公司 一种高着色强度颜料橙64的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1087301B (de) 1958-04-05 1960-08-18 Bayer Ag Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080321A (en) 1973-08-01 1978-03-21 Hoechst Aktiengesellschaft Monoazo pigments from diazotized acylamino-anilines and acetoacetylamino benzimidazolones

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CH420422A (de) 1966-09-15
DK103085C (da) 1965-11-15
BE622476A (en, 2012)
DE1227585B (de) 1966-10-27
GB1008166A (en) 1965-10-27

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