GB1579408A - Disazo compounds containing the oxadiazole residue and their use as pigments - Google Patents
Disazo compounds containing the oxadiazole residue and their use as pigments Download PDFInfo
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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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/34—Disazo dyes characterised by the tetrazo component the tetrazo component being heterocyclic
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Abstract
Bisdiazotisation of 2,5-bis(4'-aminophenyl)-1,3,4-oxadiazoles, which may be substituted in the phenyl moieties, and coupling onto 2 mol equivalents of one or more coupling components that are free of water-solubilising groups produces pigments having a clean hue, high colour strength, good dispersibility, good lightfastness, high resistance to heat and chemicals, in particular solvents, and good migration fastness.
Description
(54) DISAZO COMPOUNDS CONTAINING THE
OXADIAZOLE RESIDUE AND THEIR
USE AS PIGMENTS
(71) We, HOECHST AKTIENGESELLSCHAFT, a body corporate organised according to the laws of the Federal Republic of Germany, of 6230
Frankfurt/Main 80, Postfach 80 03 20, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to disazo compound and their use as pigments.
The present invention provides a compound of the general formula I
wherein the groups X and Y any two or more of which may be the same or different, each represents a hydrogen, chlorine, or bromine, atom, a methyl, ethyl, methoxy, or ethoxy group; and the groups K, which may be the same or different, each represents a group of the general formula II
wherein R represents a methyl or phenyl group, and Ar represents a group of the general formula Ila
wherein R1, R2 and R3, any two or all of which may be the same or different, each represents a hydrogen, chlorine or bromine atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkanoylamino group having from 2 to 5 carbon atoms, a benzoylamino or nitro group, provided that if the groups X and Y each represents a hydrogen atom at least one of R', R2 and R3 also represents a hydrogen atom, or Ar represents any group of the general formulae
wherein R4 represents a hydrogen, chlorine, or bromine atom, an alkyl or alkoxy group having from 1 to 4 carbon atoms, a carbalkoxy group having from 2 to 5 carbon atoms or a nitro group; or K represents a group of the general formula 111
wherein R5 represents phenyl, tolyl or chlorophenyl group, and R6 represents a methyl group, a carboalkoxy or alkanoylamino group having from 2 to 5 carbon atoms, or a carbamoyl group; or K represents any group of the general formulae
wherein Z represents an oxygen or sulfur atom or an imino group.
The term "lower" is used herein to denote groups having from 1 to 4 carbon atoms in the case of alkyl and alkoxy groups, and groups having a total of from 2 to 5 carbon atoms in the case of alkanoyl groups.
Examples of groups Ar of the general formula Ila include phenyl, 0, m- and ptolyl, o-, m- and p - methoxyphenyl, o-, m- and p - ethoxyphenyl, o-. m- and p chlorophenyl, o-, m- and p - bromophenyl, o-, m- and p - nitrophenyl, 2,4 dimethylphenyl, 2,5 - dimethoxyphenyl, 2,3 - dichlorophenyl, 2,4 - dichlorophenyl, 2,5 - dichlorophenyl, 2,4,5 - trichlorophenyl, 2 - chloro - 3 methylphenyl, 2 - chloro - 4 - methylphenyl, 2 - chloro - 5 - methylphenyl, 3 chloro 2 - methylphenyl, 4- chloro - 2 - methylphenyl, 2 - methoxy - 5 chlorophenyl, 2,5 - dimethoxy - 4 - chlorophenyl, 2,4 - dimethoxy - 5 - chlorophenyl, 2 - methoxy - 4 - chloro - 5 - methylphenyl, 4 - acetylaminophenyl or 4 benzoylaminophenyl.
Possible radicals Ar of the formula IIb are, in particular, benzimidazol - 2 on - 5 - yl, 7 - chloro - benzimidazol - 2 - on - 5 - yl and 7 - methyl benzimidazol - 2 - on - 5 - yl.
Examples of pyrazolone groups of the formula III include groups of 1 phenyl - 3 - methylpyrazol - 5 - one, I - (4' - tolyl) - 3 - methylpyrazol - 5 - one, - - phenyl - 3 - carbomethoxypyrazol - 5 - one, I - (4' - tolyl) - 3 carboethoxypyrazol - 5 - one or 1 - phenyl - 3 - acetylaminopyrazol - 5 - one.
The invention also provides a process for the manufacture of a compound of the general formula I, which comprises bis-diazotizing a compound of the general formula VII
wherein the groups X and Y any two or more of which may be the same or different are defined as above and coupling the bis-diazonium compound so formed with 2 equivalents of a coupling component of the formula K-H in which K is defined as above or a mixture containing two equivalents of such coupling components. The coupling may be conducted in known manner, for example in an aqueous medium.
The bis-diazotization may be performed at a temperature in the range of from -20 to +400 C, preferably from 0 to 200C and the coupling may be performed at a temperature in the range of from 0 to 400 C, preferably from 0 to 200 C. The diazo components of the formula VII can be manufactured by known processes, for example by condensation of the appropriately substituted 4 - acylaminobenzoic acid, 4 - nitrobenzoic acid or 4 - nitrobenzoic acid methyl or ethyl ester with hydrazine or salts thereof in the presence of a condensing agent, such as sulfuric acid, phosphoric acid or polyphosphoric acid, and subsequent hydrolysis of the acylamino compound or reduction of the resulting dinitro compound by known processes, such as, for example, reduction with iron dust or catalytic hydrogenation.
The bis-diazotization of the diamines of the formula VII can be carried out, for example, using alkali metal nitrites and a mineral acid, but also using nitrosylsulfuric acid. It can be useful here and also in the subsequent coupling to add surface-active agents, such as, for example, non-ionic, anionic or cationic dispersing agents.
Diazotization and coupling can also be carried out in the presence of suitable organic solvents, such as, for example, glacial acetic acid, lower alkanols, dioxan, formamide, dimethylformamide, dimethylsulfoxide, pyridine or N methylpyrrolidone. In order to achieve the full tinctorial strength and a particularly favorable crystal structure, it is often desirable for the coupling product to be thermally aftertreated, preferably at a temperature of up to 2000 C. The thermal aftertreatment may, for example, be conducted by boiling the coupling mixture or by keeping it at a temperature of above 100"C under pressure, optionally in the presence of an organic solvent, such as ethanol, o-dichlorobenzene, dimethylformamide or N-methylpyrrolidone, or in the presence of resin soap.Particularly pure pigments of high tinctorial strength are obtained with the products according to the invention if, after coupling, the moist press cakes or the dried powders are subjected to the thermal aftertreatment in organic solvents, such as alcohols, for example lower alkanols, pyridine, glacial acetic acid, diemthylformamide, N methyl - pyrrolidone, dimethylsulfoxide or aromatic solvents, such as chlorobenzene, dichlorobenzene or nitrobenzene, or if the pigments are subsequently ground, grinding auxiliaries being added.
The compounds of the invention can also be manufactured in the presence of a carrier, for example baryte.
The invention also provides a process for pigmenting an article which comprises treating the article with a compound according to the invention.
The new pigments are water-insoluble and insoluble in the customary organic solvents and are suitable for the manufacture of printing inks, gloss paints and emulsion paints, and for dyeing rubber, plastics and natural or synthetic resins.
Furthermore, they are suitable for pigment printing onto substrates, in particular textile fiber materials or other sheet-like structures, such as, for example, paper.
The pigments can also be used in other fields of application, for example in the finely divided form for dyeing rayon made from viscose or cellulose ethers or esters, polyamides, polyurethanes, polyglycol terephthalate or polyacrylonitriles in the spinning composition, or for dyeing paper.
The pigments can be readily processed in the media mentioned. The dyeings have clear shades and very good depths of color and are fast to light, and are stable towards the action of heat and the influence of chemicals, above all solvents.
The following Examples illustrate the invention, Unless indicated otherwise, figures given as percentages refer to percent by weight.
Example 1
16.6 g of 2,5 - bis - [4' - amino - 3' - chloro - phenyl - (1')] - 1,3,4 - oxadiazole are stirred for several hours in 100 ml of glacial acetic acid and 25 ml of 31% strength hydrochloric acid. The suspension is then cooled to OOC with ice and is diluted to about 300 ml with water. The oxadiazole is rapidly diazotized with 13.5 ml of 400/ strength sodium nitrite solution. The mixture is stirred for a further one hour with a slight excess of nitrite and then clarified over a layer of kieselguhr.
18.6 g of N - acetoacetyl - aniline are dissolved in 600 ml of water and 15 ml of 33 /n strength sodium hydroxide solution. 2 g of an emulsifier consisting of oxyethylated hydrogenated tallow fat alcohol are added. 20 ml of glacial acetic acid are added dropwise at 150C. The diazo solution, which has been freed from excess nitrite beforehand using a little amidosulfonic acid, is added dropwise to the suspension, thus obtained, at 2--25"C in the course of one hour. During this addition, the pH value is kept at 5.5 by simultaneously running in dilute sodium hydroxide solution. After the coupling has ended, the mixture is heated to 950C for 30 minutes. The product is isolated, washed with water until salt-free, dried and powdered.
37 g of a greenish-tinged yellow pigment of the formula
of outstanding fastness to light and high tinctorial strength are obtained.
Example 2
12.6 g of 2,5 - bis - [4' - amino - phenyl - (1')] - 1,3,4 - oxadiazole are stirred overnight in 100 ml of glacial acetic acid and 25 ml of 31% strength hydrochloric acid. The next day, the temperature is adjusted to OOC with ice and water and the volume is adjusted to 300 ml. The oxadiazole is diazotized with 13.2 ml of 40% strength sodium nitrite solution. The mixture is stirred for a further 30 minutes and clarified over a layer of kieselguhr.
21.8 g of N - acetoacetyl - 4 - methoxy - aniline are dissolved in 600 ml of water with 15 ml of 33% strength sodium hydroxide solution. 2 g of an emulsifier consisting of oxyethylated, hydrogenated tallow fat alcohol are added. The coupling component is precipitated with 20 ml of glacial acetic acid at 150C. 0.5 g of amidosulfonic acid is added and the diazonium salt solution is added dropwise at 20"C in the course of one hour. The pH value is kept at 5.5 by simultaneously running in dilute sodium hydroxide solution. After the coupling has ended, the pigment suspension is heated to 950C for 30 minutes. The solid is filtered off at 70"C, washed, dried and powdered. 34.5 g of a greenish-tinged yellow pigment having the structural formula
are obtained.
This pigment is distinguished by high tinctorial strength, purity of color shade and good fastness to light and migration.
Example 3
24.3 g of N - acetoacetyl - 2 - methoxy - aniline are used instead of N acetoacetyl - aniline in Example 1. 39 g of a yellow pigment of the formula
are obtained according to the process described in Example 1.
The pigment powder is stirred in dimethylsulfoxide at 15(w1600C for 1, hours. After cooling the mixture to 700C, the pigment is filtered off, washed with methanol, dried and powdered. A slightly greenish-tinged yellow pigment of excellent fastness to light and very good tinctorial strength is obtained.
Example 4
16.1 g of 2,5 - bis - [4' - amino - 2' - chloro - phenyl - (1')] - 1,3,4 - oxadiazole are stirred overnight in 100 ml of glacial acetic acid and 50 ml of 31 strength hydrochloric acid. The next day, the temperature is adjusted to 0 C by adding ice. The oxadiazole is diazotized with 13.2 ml of 40'/n strength sodium nitrite solution and the mixture is stirred for a further one hour with a slight excess of nitrite. A clear diazonium salt solution is obtained.
21.6 g of N - acetoacetyl - 2,4 - dimethyl - aniline are made into a slurry with 600 ml of water and are dissolved with 20 ml of 33% strength sodium hydroxide solution. 15 ml of glacial acetic acid and 0.5 g of amidosulfonic acid are added at 150C. The diazonium salt solution is added dropwise to the resulting suspension at 200C in the course of one hour. During this addition, the pH value is kept at 5.0 by simultaneously running in dilute sodium hydroxide solution. After the coupling has ended, the pigment suspension is heated to 900C for 15 minutes. The pigment is then filtered off, washed until salt-free, dried and powdered. Yield: 38 g.
20 g of this pigment powder having the structural formula
are stirred in 250 ml of dimethylformamide at 1 100C for 20 minutes. The solid is filtered off at 700C, washed with ethanol, dried and powdered. 19 g of a yellow pigment of high tinctorial strength and good fastness to light are obtained.
Example 5
16.1 g of 2,5 - bis - [4' - amino - 2' - chloro - phenyl - (1')] - 1,3,4 - oxadiazole are stirred overnight in 50 ml of 31% strength hydrochloric acid and 45 ml of water. The next day, the mixture is cooled to OOC with ice and the oxidazole is diazotized with 13.2 ml of 40% strength sodium nitrite solution. The mixture is stirred for a further hour with a slight excess of nitrite and then clarified over a layer of kieselguhr. The filtrate is made up to 400 ml with water, and 1 g of an emulsifier consisting of oxyethylated, hydrogenated tallow fat alcohol is added.
20 g of 3 - methyl - 1 - (4' - tolyl) - pyrazol - 5 - one are dissolved in 200 ml of water with 11 ml of 33% strength sodium hydroxide solution. This solution is added dropwise to the diazonium salt solution at 10--200C in the course of 1 hour.
After the coupling has ended, the mixture is heated to 950C for 30 minutes. The solid is then filtered off at 700 C, washed until salt-free, dried and powdered. 35 g of a reddish-tinged yellow pigment of the following structural formula are obtained:
This pigment is distinguished, in particular, by its outstanding tinctorial strength.
Example 6
The diazonium salt solution is prepared according to Example 1, but four times the amount of 31 /n strength hydrochloric acid is employed in the salt formation.
24.4 g of 5-acetoacetylamino-benzimidazolone are dissolved in 440 ml of water and 28.4 ml of 33% strength sodium hydroxide solution. 20 ml of glacial acetic acid are added dropwise to the clear solution of the coupling component at 150C. The diazo solution is added dropwise to the suspension, thus obtained, at a temperature of 20"C in the course of 80 minutes. The pH value is kept at 5.0 by simultaneously running in dilute sodium hydroxide solution. After the coupling has ended, the mixture is heated to 950C for 30 minutes. The pigment is filtered off at 700C, washed with water until salt-free, dried and powdered. 45 g of a pigment having the following structural formula are obtained:
20 g of the pigment thus obtained are heated to 1800C in 400 ml of
dimethylsulfoxide for 40 minutes.The mixture is allowed to cool to 700 C, the solid
is filtered off and the filter cake is washed with methanol. Drying and powdering
give 17 g of a reddish-tinged yellow pigment. This pigment is distinguished by very
good tinctorial strength, excellent fastness to solvents and migration and
outstanding fastness to light.
Example 7
7.9 g of 2,5 - bis - [4' - amino - 2' - methyl - phenyl - (1)1 - 1,3,4
oxadiazole are stirred overnight in 150 ml of glacial acetic acid and 15 ml of 31%
strength hydrochloric acid. The mixture is then adiusted to 100C with ice and the
oxadiazole is bis-diazotized by rapidly adding 10 ml of 5 N sodium nitrite solution.
The mixture is subsequently stirred for a further 30 minutes with a slight excess of
nitrite. 14.3 g of aceto - acetyl - 2,5 - dimethoxy - 4- chloroaniline are
introduced into 80 ml of water. The compound is then dissolved with 6 ml of 33%
strength sodium hydroxide solution, and the solution is clarified with a little active
charcoal and kieselguhr. The clarified solution is allowed to run into a mixture of 5
ml of glacial acetic acid and 1 g of a 10% strength aqueous solution of a stearyl alcohol, oxyethylated with 20 mols of ethylene oxide, in 100 ml of ice-water.
The diazonium salt solution described above is allowed to run at room temperature into the suspension thus prepared, after the excess of nitrite has been removed with a little amidosulfonic acid solution, the pH value simultaneously being kept at 5.5 with 6% strength sodium hydroxide solution. After the addition has ended, the mixture is heated to 950C and kept at this temperature for 30 minutes. The greenish-tinged yellow pigment is filtered off, washed with water until salt-free and dried at 650C.
If the crude pigment is treated with 50 ml of dimethylformamide at 1000C for 30 minutes, after filtering off the precipitate, washing and drying 17.4 g of the yellow pigment, of high tinctorial strength, of the formula
are obtained.
Further examples which were prepared according to the examples described are summarized in the following Table:
Color shade
X Y K-H (letterpress printing)
H H . N-Acetoacetyl-aniline greenish-tinged yellow
H H N-acetoacetyl-2-methylaniline yellow
H H N-acetoacetyl-4-methylaniline yellow
H H N-acetoacetyl-2,4-dimethylaniline yellow
H H N-acetoacetyl-2-methoxyaniline greenish-tinged yellow
H H N-acetoacetyl-2-chloroaniline reddish-tinged yellow
H H N-acetoacetyl-4-chloroaniline reddish-tinged yellow
H H N-acetoacetyl-2,5-dichloroaniline reddish-tinged yellow
H H N-acetoacetyl-2-methyl-4-chloroaniline reddish-tinged yellow
Color shade
X Y K-H (letterpress printing)
H H N-acetoacetyl-2-methoxy-5-chloroaniline reddish-tinged yellow
H H 5-acetoacetylamino-benzimidazolone yellow
H H 5-acetoacetylamino-7-methylbenzimidazolone reddish-tinged yellow
H H 5-acetoacetylamino-7-chlorobenzimidazolone reddish-tinged yellow
H H l-phenyl-3-methylpyrazol-5-one reddish-tinged yellow
H H l-(4'-tolyl)-3-methylpyrazol-5-one reddish-tinged yellow
H H barbituric acid yellowish-tinged orange
Cl H N-acetoacetyl-2-methyl-aniline greenish-tinged yellow
Cl H N-acetoacetyl-4-methyl-aniline greenish-tinged yellow
Cl H N-acetoacetyl-2,4-dimethyl-aniline greenish-tinged yellow
Cl H N-acetoacetyl-4-methoxy-aniline yellow
Cl H N-acetoacetyl-2-chloro-aniline greenish-tinged yellow
Cl H N-acetoacetyl-4-chloro-aniline yellow
Cl H N-acetoacetyl-2,5-dichloro-aniline greenish-tinged yellow
Cl H N-acetoacetyl-4-chloro-2-methyl-aniline greenish-tinged yellow
Cl H N-acetoacetyl-5-chloro-2-methoxy-aniline yellow
Cl H N-acetoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow
Cl H 5-acetoacetylamino-7-chloro-benzimidazolone reddish-tinged yellow
Cl H 3-methyl-l-phenyl-pyrazol-5-one reddish-tinged yellow
Cl H 3-methyl-I -(4'-tolyl)-pyrazol-5-one reddish-tinged yellow
Cl H barbituric acid yellow
H Cl N-acetoacetyl-aniline greenish-tinged yellow
H Cl N-acetoacetyl-2-methylaniline greenish-tinged yellow
H Cl N-acetoacetyl-4-methylaniline greenish-tinged yellow
H Cl N-acetoacetyl-2-methoxyaniline greenish-tinged yellow
H Cl N-acetoacetyl-4-methoxyaniline greenish-tinged yellow
H Cl N-acetoacetyl-2-chloroaniline greenish-tinged yellow
H Cl N-acetoacetyl-4-chloroaniline greenish-tinged yellow
H Cl N-acetoacetyl-2,5-dichloroaniline reddish-tinged yellow
H Cl N-acetoacetyl-4-chloro-2-methylaniline greenish-tinged yellow
H Cl N-acetoacetyl-5-chloro-2-methoxyaniline reddish-tinged yellow
H Cl N-acetoacetyl-4-chloro-2, 5-dimethoxyaniline reddish-tinged yellow
H Cl 5-acetoacetylaminobenzimidazolone reddish-tinged yellow
H Cl 5-acetoacetylamino-7-chloro-benzimidazolone reddish-tinged yellow
H Cl 3-methyl- 1 -phenyl-pyrazol-5-one reddish-tinged yellow
OCH3 H N-acetoacetyl-2,4-dimethyl-aniline reddish-tinged yellow
OCH3 H N-acetoacetyl-2-methoxy-aniline yellow
OCH3 H N-acetoacetyl-4-chloro-aniline reddish-tinged yellow
OCH3 H 5-acetoacetylamino-benzimidazolone reddish-tinged yellow
OCH3 H 3-methyl- 1 -(4'-tolyl)-pyrazol-5-one yellowish-tinged orange OC2H5 H N-acetoacetyl-4-methoxy-aniline reddish-tinged yellow
H OCH3 N-acetoacetyl-4-methyl-aniline reddish-tinged yellow
H OCH3 N-acetoacetyl-4-methoxy-aniline reddish-tinged yellow
H OCH3 N-acetoacetyl-2,5-dichloro-aniline orange
H OCH3 N-acetoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow H OCH3 3-methyl- 1-phenyl-pyrazol-5-one yellowish-tinged orange Cl Cl N-acetoacetyl-aniline greenish-tinged yellow
Cl Cl N-acetoacetyl-2,4-dimethyl-aniline greenish-tinged yellow
Cl Cl N-acetoacetyl-2-methoxy-aniline greenish-tinged yellow
Cl Cl N-acetoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow
Cl Cl 5-acetoacetylamino-benzimidazolone reddish-tinged yellow
Cl Cl 3-methyl-1-phenyl-pyrazol-5-one yellowish-tinged orange
Br H N-acetoacetyl-4-methoxy-aniline yellow
Br H 3-methyl- 1 -(4'-tolyl)-pyrazol-5-one orange
CH3 H N-acetoacetyl-2,4-dimethyl-aniline greenish-tinged yellow
CH3 H N-acetoacetyl-4-methoxy-aniline greenish-tinged yellow
CH3 H N-acetoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow
CH3 H 5-acetoacetylamino-benzimidazolone reddish-tinged yellow
CH3 H 3-methyl-I -phenyl-pyrazol-5-one yellowish-tinged orange C3H5 H N-acetoacetyl-2-methoxy-aniline greenish-tinged yellow
H CH3 5-acetoacetylamino-benzimidazolone reddish-tinged yellow
H CH3 N-acetoacetyl-2,4-dimethyl-aniline greenish-tinged yellow
H CH3 N-acetoacetyl-aniline greenish-tinged yellow
Color shade
X Y K-H (letterpress printing)
H CH3 N-acetoacetyl-2-methoxy-aniline greenish-tinged yellow
H CH3 3-methyl-I -(4'-tolyl)-pyrazol-5-one yellowish-tinged orange
Cl CH3 N-ac etoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow
H Cl 6-N-acetoacetylamino-tetrahydroquinoxaline- reddish-tinged yellow
2,3-dione
H Cl 6-N-acetoacetylamino-tetrahydroquinazoline- reddish-tinged yellow
2,4-dione
Cl H N-acetoacetylaminophthalimide yellow
Cl H 6-N-acetoacetylaminotetrahydrophthalazine- brownish-tinged yellow
2,3-dione
Cl H 2,6-dihydroxy-4-methyl-5-cyanopyridine brown
Cl H 2,4-dihydroxyquinoline brown
WHAT WE CLAIM IS:1. A compound of the general formula I
wherein the groups X and Y any two or more of which may be the same or different, each represents a hydrogen, chlorine, or bromine, atom, a methyl, ethyl, methoxy, or ethoxy group; and the groups K, which may be the same or different, each represents a group of the general formula II
wherein R represents a methyl or phenyl group, and Ar represents a group of the general formula IIa
wherein R1, R2 and R3 any two or all of which may be the same or different, each represents a hydrogen, chlorine or bromine atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkanoylamino group having from 2 to 5 carbon atoms, a benzoylamino or nitro group, provided that if the groups X and Y each represents a hydrogen atom, at least one of R', R2 and R3 also represents a hydrogen atom, or Ar represents any group of the general formulae
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (20)
- **WARNING** start of CLMS field may overlap end of DESC **.Color shade X Y K-H (letterpress printing) H CH3 N-acetoacetyl-2-methoxy-aniline greenish-tinged yellow H CH3 3-methyl-I -(4'-tolyl)-pyrazol-5-one yellowish-tinged orange Cl CH3 N-ac etoacetyl-4-chloro-2,5-dimethoxy-aniline reddish-tinged yellow H Cl 6-N-acetoacetylamino-tetrahydroquinoxaline- reddish-tinged yellow 2,3-dione H Cl 6-N-acetoacetylamino-tetrahydroquinazoline- reddish-tinged yellow 2,4-dione Cl H N-acetoacetylaminophthalimide yellow Cl H 6-N-acetoacetylaminotetrahydrophthalazine- brownish-tinged yellow 2,3-dione Cl H 2,6-dihydroxy-4-methyl-5-cyanopyridine brown Cl H 2,4-dihydroxyquinoline brown WHAT WE CLAIM IS:1.A compound of the general formula Iwherein the groups X and Y any two or more of which may be the same or different, each represents a hydrogen, chlorine, or bromine, atom, a methyl, ethyl, methoxy, or ethoxy group; and the groups K, which may be the same or different, each represents a group of the general formula IIwherein R represents a methyl or phenyl group, and Ar represents a group of the general formula IIawherein R1, R2 and R3 any two or all of which may be the same or different, each represents a hydrogen, chlorine or bromine atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkanoylamino group having from 2 to 5 carbon atoms, a benzoylamino or nitro group, provided that if the groups X and Y each represents a hydrogen atom, at least one of R', R2 and R3 also represents a hydrogen atom, or Ar represents any group of the general formulaewherein R4 represents a hydrogen, chlorine, or bromine atom, an alkyl or alkoxy group having from 1 to 4 carbon atoms, a carbalkoxy group having from 2 to 5 carbon atoms or a nitro group; or K represents a group of the general formula IIwherein R5 represents phenyl, tolyl or chlorophenyl group, and R6 represents a methyl group, a carboalkoxy or alkanoylamino group having from 2 to 5 carbon atoms, or a carbamoyl group; or K represents any group of the general formulaewherein Z represents an oxygen or sulfur atom or an imino group.
- 2. A compound of the general formula I as defined in claim 1, wherein the groups K which may be the same or different, each represent a group of the general formulawherein R, R1, R2 and R3 are defined as in claim 2.
- 3. A compound as claimed in claim 1, wherein X and Y which may be the same or different, each represents a hydrogen or chlorine atom.
- 4. A compound as claimed in claim 1, wherein R represents a methyl group.
- 5. A compound as claimed in claim 1, wherein X and Y each represent a hydrogen atom and K represents a group of the formula
- 6. A compound as claimed in claim 1, wherein X represents a chlorine atom, Y represents a hydrogen atom and K represents a group of the formula
- 7. A compound as claimed in claim 1, wherein X represents a hydrogen atom, Y represents a chlorine atom and K represents a group of the formula
- 8. A compound as claimed in claim 1, wherein X represents a hydrogen atom, Y represents a chlorine atom and K represents a group of the formula
- 9. A compound as claimed in claim 1, wherein X represents a hydrogen atom, Y represents a chlorine atom and K represents a group of the formula
- 10.A process for the preparation of a compound as claimed in claim 1, which comprises bis-diazotizing a compound of the formulawherein the groups X and Y, any two or more of which may be the same or different, are defined as in claim 1, and coupling the diazonium salt so formed with two equivalents of an azoic coupling component of the formula K-H, wherein K is defined as in claim 1, or a mixture containing two equivalents of such azoic coupling components.
- 11. A process as claimed in claim 10, wherein the bis-diazotization is performed at a temperature in the range of from -20 to +400C.
- 12. A process as claimed in claim 11, wherein the temperature is in the range of from 0 to 200C.
- 13. A process as claimed in any one of claims 10 to 12, wherein the coupling is performed at a temperature in the range of from 0 to 400 C.
- 14. A process as claimed in claim 13, wherein the temperature is in the range of from 0 to 200C.
- 15. A process as claimed in any one of claims 10 to 14, wherein the coupling product is thermally aftertreated.
- 16. A process as claimed in claim 15 wherein the thermal aftertreatment is performed at a temperature of up to 2000C.
- 17. A process as claimed in any one of claims 10 to 16 which is performed in an organic solvent.
- 18. Any process for the preparation of a disazo compound conducted substantially as described in any one of the Examples herein.
- 19. A process for pigmenting an article which comprises treating the article with a compound as claimed in claim 1.
- 20. A pigmented article whenever obtained by a process as claimed in claim 19.v r O t x r
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762659706 DE2659706C3 (en) | 1976-12-31 | 1976-12-31 | Disazo compounds, processes for their production and their use as pigments, for coloring plastics, rubber, paper and for the production of printing, lacquer and paints |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1579408A true GB1579408A (en) | 1980-11-19 |
Family
ID=5997126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5419077A Expired GB1579408A (en) | 1976-12-31 | 1977-12-29 | Disazo compounds containing the oxadiazole residue and their use as pigments |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5385824A (en) |
| BE (1) | BE862588A (en) |
| BR (1) | BR7708793A (en) |
| CH (1) | CH637152A5 (en) |
| DE (1) | DE2659706C3 (en) |
| FR (1) | FR2376193A1 (en) |
| GB (1) | GB1579408A (en) |
| IN (1) | IN148061B (en) |
| IT (1) | IT1089241B (en) |
| MX (1) | MX147095A (en) |
| NL (1) | NL7714316A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4509948A (en) * | 1982-08-24 | 1985-04-09 | Bayer Aktiengesellschaft | Cationic mono- and dis-azo dyestuffs, and their preparation and use for dyeing paper and cationic dyeable substrates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE929498C (en) * | 1953-07-01 | 1955-06-27 | Hoechst Ag | Process for the production of water-insoluble azo dyes |
| DE1000117B (en) | 1954-07-07 | 1957-01-03 | Ciba Geigy | Process for the production of 1, 3, 4-oxdiazole compounds containing azo groups |
| JPS5168629A (en) * | 1974-12-12 | 1976-06-14 | Nippon Kayaku Kk | SHINKIJISUAZOGANRYONO SEIZOHO |
-
1976
- 1976-12-31 DE DE19762659706 patent/DE2659706C3/en not_active Expired
-
1977
- 1977-12-16 MX MX17181377A patent/MX147095A/en unknown
- 1977-12-23 NL NL7714316A patent/NL7714316A/en not_active Application Discontinuation
- 1977-12-26 IN IN1769/CAL/77A patent/IN148061B/en unknown
- 1977-12-27 JP JP15674577A patent/JPS5385824A/en active Granted
- 1977-12-29 IT IT3141477A patent/IT1089241B/en active
- 1977-12-29 GB GB5419077A patent/GB1579408A/en not_active Expired
- 1977-12-30 BR BR7708793A patent/BR7708793A/en unknown
-
1978
- 1978-01-02 FR FR7800011A patent/FR2376193A1/en active Granted
- 1978-01-02 BE BE184067A patent/BE862588A/en unknown
- 1978-01-03 CH CH3478A patent/CH637152A5/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4509948A (en) * | 1982-08-24 | 1985-04-09 | Bayer Aktiengesellschaft | Cationic mono- and dis-azo dyestuffs, and their preparation and use for dyeing paper and cationic dyeable substrates |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7708793A (en) | 1978-08-15 |
| DE2659706B2 (en) | 1979-03-15 |
| BE862588A (en) | 1978-07-03 |
| DE2659706A1 (en) | 1978-07-13 |
| FR2376193A1 (en) | 1978-07-28 |
| FR2376193B1 (en) | 1983-01-21 |
| NL7714316A (en) | 1978-07-04 |
| CH637152A5 (en) | 1983-07-15 |
| MX147095A (en) | 1982-10-05 |
| IN148061B (en) | 1980-10-11 |
| JPS6127415B2 (en) | 1986-06-25 |
| JPS5385824A (en) | 1978-07-28 |
| DE2659706C3 (en) | 1979-11-08 |
| IT1089241B (en) | 1985-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |