US2112276A - Coloration of textile materials - Google Patents

Coloration of textile materials Download PDF

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US2112276A
US2112276A US44558A US4455835A US2112276A US 2112276 A US2112276 A US 2112276A US 44558 A US44558 A US 44558A US 4455835 A US4455835 A US 4455835A US 2112276 A US2112276 A US 2112276A
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coupling
amino
coloration
diazo
textile materials
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US44558A
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Ellis George Holland
Kirk Ernest William
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Celanese Corp
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Celanese Corp
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/68—Preparing azo dyes on the material

Definitions

  • This invention is a division of U. S. Patent No. 2,040,927, filed 6th October 1932 and relates to the coloration of textile materials and more particularly to the coloration of such materials by the so-called azoic process wherein insoluble or difficultly soluble azo dyes are formed on the matrials by the coupling thereon of diazo compounds and suitable coupling components.
  • the colorations so produced exhibit very good fastness properties, particularly in respect of fastness to hot soaping treatments.
  • the latter is a point of particular importance in the case of yarns, particularly artificial yarns 'which are to be woven with silk in the gummed state and so are called upon to resist the de-gumming treatment to which the resulting fabrics are neces- 50 sarily subjected.
  • our invention comprises the coloration of textile materials by coupling therein suitable coupling components with diazo compounds of 1 amino 4 mono substituted-amino-anthraqui- 55 nones wherein the substituent in the amino group in the 4-position is an alkyl, aryl, or aralkyl group.
  • a Wide range of diazotizable amino-anthraquinone derivatives is available for use in accordance with the present invention, unsul- 5 phonated compounds being preferably employed.
  • unsul- 5 phonated compounds being preferably employed.
  • diazo components which may be employed there may be mentioned 1-amino-4-phenylamino- 10 anthraquinone.
  • 1-amino-4-para-tolylamino-anthraquinone 1-amino-4-para-anisylamino-anthraquinone; 1:S-diamino-4.8-para-tolylaminoanthraquinone, l-amino-4-phenylamino-5-oxyanthraquinone, and 1:5-diamino-4-phenylamino 15 anthraquinone.
  • Various coupling components may be utilized for the formation of dyestuffs by reaction with the foregoing diazo components, particularly coupling components which couple in an aryl 20 nucleus, for example aromatic amines or phenols, whether of the benzene, naphthalene or other series.
  • diazo components particularly coupling components which couple in an aryl 20 nucleus, for example aromatic amines or phenols, whether of the benzene, naphthalene or other series.
  • compounds containing methylene groups capable of reacting with diazo compounds may be used, for example pyraz'olone derivatives 25 or acidyl-acetic esters or acidyl-aceticamides or substituted amides, or other B-keto-acidyl compounds.
  • coupling components capable of yielding with diazo compounds azo 30 dyestufi's of very difiicultly soluble character and having little or no aflinity for textile materials, whether natural or artificial, when applied thereto in substance.
  • Examples of such coupling components are the acidylamino coupling com- 35 ponents referred to in British Patent No. 404,363, and. other amides and substituted amides, particularly aryl-amides, of hydroxy carboxylic acids especially ortho-hydroxy carboxylic acids, of the benzene, naphthalene, carbazole and other series.
  • Mention may be made, for instance, of the anilides and naphthalides and substituted anilides or naphthalides of salicylic acid and its homologues, or of 2:3- or 1:4-oxy-naphthoic acid, for example 2:3oxy-naphthoic-ortho-toluidine or meta-nitranilide.
  • Compounds containing more than one hydroxy carboxylic acid residue may also be used, for instance the di(2:3-oxy-naph thoyl) dianisidine...
  • Another class of coupling component yielding difiicultly soluble dyestufls is the class of di-B-keto-acidyl derivatives of arcmatic diamines, for example the d acetoacetyl derivative of ortho-tolidine or other aromatic diamines.
  • Incoloring textile materials in accordance with the new azoic process various modes of working may be adopted.
  • the materials impregnated with the coupling components may be treated with solutions of the diazo compounds.
  • the diazo component may be applied first, diazotized on the material and the latter thereafter subjected to the action of the coupling component.
  • Another method of operation consists in applying both the diazo component and the coupling component to the materials, either together or separately and thereafter subjecting the materials to treatment adapted to effect diazotization of the diazo component and coupling with the coupling component.
  • the new processes may be utilized either for the uniform or for the local coloration of materials.
  • the components may be applied by dyeing methods, or, if desired, by mechanical impregnation, for instance by padding or by all-over printing.
  • printing, stencilling or any other desired means may be employed, whether the components are applied together or separately or whether diazotization is effected on the material or in a separate operation.
  • the dispersions of the diazo or coupling components may be obtained by any desired method, for. example by fine milling or grinding with or without the aid of dispersators and/or protective colloids, by precipitation in the presence of protective colloids, or by a simple treatment with dispersators, as described for instance in any of U. S. Patents Nos. 1,618,413, 1,618,414, 1,694,413, 1,690,481, 1,803,008, 1,840,572, 1,716,721, 1,928,647 and 1,959,352.
  • the dispersion of the coupling component may be facilitated by the presence of small quantities of alkali, for
  • caustic soda sufllcient to' yield a preparation of about pH 8 to 9 or even slightly more alkaline.
  • cellulose ester and ether materials In treating cellulose ester and ether materials the absorption of either or both components may be facilitated if desired by incorporating swelling agents in the dyeing or padding liquors or printing pastes employed, or the materials may be pretreated with swelling agentsm Alcohol is particularly suitable for this purpose, though other swelling agents may be employed if desired.
  • the coupling component in the form of an alkali metal salt, for instance by a paddingirea'tment.
  • the impregnated material is thereafter developed in a solution of the desired diazo compound, or such a solution, if necessary suitably thickened, applied by printing or other mode of local application, where localized color efiects are required.
  • this invention is of especial value in connection with the coloration of cellulose ester and ether materials.
  • the invention may be applied to cellulose formate, propionate or butyrate or ethyl or benzyl cellulose materials.
  • Other materials may also be colored by the new process, for instance wool, silk and other animal fibres, also mixed materials of all kinds, for instance materials containing both animal and vegetable fibres or materials containing cellulose acetate or other artificial fibres in conjunction with cotton or other natural fibres.
  • the coupling components are preferably applied from very weakly alkaline baths, or even in the form of dispersions of the free compounds; in fact the methods specified as suitable for the treatment of cellulose ester and ether materials may in general be applied with satisfaction for the coloration of animal fibres.
  • Example 1 To dye 10 kilogrammes of cellulose acetate yarn a full nigger brown of good fastness to water, 100 grammes of 1 amino 4 paratolylamino-E-hydroXy-anthraquinone are dispersed by boiling with 300 grammes of Turkey red oil and diluting with about 10 litres of hot soft water, and added to a dyebath of 300 litres of soft water.
  • the yarn is entered and worked in this bath for two hours; duringthe first half-hour the temperature being raised to 70 C. and maintained at this temperature for the remainder of the dyeing period.
  • the yarn is then liftedand entered into a diazotizing bath containing 6 grammes per litre sodium nitrite and 12 cos.
  • organic derivative of cellulose connotes a cellulose ester of an organic acid or a cellulose ether.
  • Process for the coloration of textile materials which comprises coupling thereon an azo coupling component, said component being one which couples in an aryl residue, with a diazo compound obtainable by diazotizing a compound. selected from the group consisting of l-amino- 4-mono-alkylamino-anthraquinones, l-amino dmono-arylamino-anthraquinones, and l-amino- -mono-aralkylamino-anthraquinones.
  • Process for the coloration of organic derivative of cellulose textile materials which comprises coupling thereon an azo coupling component, said 1 component being one which couples in an aryl residue, with a diazo compound obtainable by di azotizing a compound selected from the group consisting of 1-aminol-mono-allrylamino-anthraquinones, 1 amino-4-mono-arylamino-anthraquinones, and 1 amino 4 mono-arallrylamino 4 mono arylamino-anthraquincnes, and l-aminol-mono aralkylamino-anthraquinones.
  • Process for the coloration of cellulose acetate textile materials which comprises coupling thereon an arylamide of an aromatic hydroxy carboxylic acid with a diazo compound obtainable by diazotizing a 1-amino-4-mono-arylamino-anthraquinone.
  • Process for the coloration of textile materials which comprises coupling thereon an arylamide of 2:3-oxy-naphthoic acid with a diazo compound obtainable by diazotizing a 1-arninol-mono-arylaminoanthrawpuinone.
  • Process for the coloration of cellulose acetate textile materials which comprises coupling thereon an arylamide of 2:3-oxy-naphthoic acid with a diazo compound obtainable by diazotizing a 1- amino-4-mono-arylamino-anthraquinone.
  • Process for the coloration of cellulose acetate textile materials which comprises coupling thereon metahydroxy-diphenylamine with a diazo compound obtainable by diazotizing a1- amino-a-mono-arylarnino-anthraquinone.
  • Process for the coloration of textile materials which comprises coupling thereon resorcinol with a diazo compound obtainable by diazotizing a 1-amino l-mono-arylamino-anthraquinone.
  • Process for the coloration of cellulose acetate textile materials which comprises coupling thereon resorcinol with a diazo compound obtainable by diazotizing a l-aminol-monoarylamino-anthraquinone.
  • Process for the coloration of cellulose acetate textile materials which comprises coupling thereon meta-hydroxy-diphenylamine with a diazo compound obtainable by diazotizing 1- amino--phenylarnino-anthraquinone.
  • Textile materials colored with an azo dyestuff obtainable by coupling an arylamide of a hydrorry carboxylic acid with a diazo compound obtainable by diazotizing a 1-amino-4-mon0- arylamino-anthraquinone.

Description

Patented Mar. 29, 1938 UNITED STATES PATENT OFFICE COLORATION OF TEXTILE MATERIALS George Holland Ellis and Ernest William Kirk, Spondon, near Derby, England, assignors to Oelanese Corporation'of America, a corporation of Delaware 1'6 Claims.
This invention is a division of U. S. Patent No. 2,040,927, filed 6th October 1932 and relates to the coloration of textile materials and more particularly to the coloration of such materials by the so-called azoic process wherein insoluble or difficultly soluble azo dyes are formed on the matrials by the coupling thereon of diazo compounds and suitable coupling components.
The coloration of cellulosic materials by the azoic process has long been practised on an extensive scale and as an example may be mentioned the production of the well-known paranitraniline red on cotton materials from diazotized para-nitraniline and fi-naphthol. During the past decade the scope of the azoic process has been very largely extended by the introduction of new coupling components, more particularly arylamides of 2:3-oxy-naphthoic acid and the diaceto-acetyl derivatives of aromatic diamines,
of which the diaceto-acetyl-ortho-tolidine is possibly the best known example. By the use of these coupling components in conjunction with diazo compounds, especially those of the benzene and naphthalene series, a wide range of colorations has been produced, many of which exhibit outstanding properties of fastness, particularly to the action of light or the action of hot alkaline or soap solutions. In this series of colors, however, there has in the past been a marked lack of certain colors, particularly blues and greens.
We have found that l-aminol-mono-substitutedFamino-anthraquinones wherein the substituent in the amino group in the 4-position is an alkyl, aryl, or aralkyl radical, constitute very valuable diazo components for the production of colorations on textile materials by the azoic process. By employing these diazo components we have found it possible to produce blue, violet and brown shades and thus extend considerably the range of shades obtainable by azoic processes.
Further, the colorations so produced exhibit very good fastness properties, particularly in respect of fastness to hot soaping treatments. The latter is a point of particular importance in the case of yarns, particularly artificial yarns 'which are to be woven with silk in the gummed state and so are called upon to resist the de-gumming treatment to which the resulting fabrics are neces- 50 sarily subjected.
Broadly our invention comprises the coloration of textile materials by coupling therein suitable coupling components with diazo compounds of 1 amino 4 mono substituted-amino-anthraqui- 55 nones wherein the substituent in the amino group in the 4-position is an alkyl, aryl, or aralkyl group.
A Wide range of diazotizable amino-anthraquinone derivatives is available for use in accordance with the present invention, unsul- 5 phonated compounds being preferably employed. Especial mention may be made of l-amino-4- arylamino-anthraquinones. As specific examples of diazo components which may be employed there may be mentioned 1-amino-4-phenylamino- 10 anthraquinone. 1-amino-4-para-tolylamino-anthraquinone, 1-amino-4-para-anisylamino-anthraquinone; 1:S-diamino-4.8-para-tolylaminoanthraquinone, l-amino-4-phenylamino-5-oxyanthraquinone, and 1:5-diamino-4-phenylamino 15 anthraquinone.
Various coupling components may be utilized for the formation of dyestuffs by reaction with the foregoing diazo components, particularly coupling components which couple in an aryl 20 nucleus, for example aromatic amines or phenols, whether of the benzene, naphthalene or other series. Again compounds containing methylene groups capable of reacting with diazo compounds may be used, for example pyraz'olone derivatives 25 or acidyl-acetic esters or acidyl-aceticamides or substituted amides, or other B-keto-acidyl compounds.
Of particular value are coupling components capable of yielding with diazo compounds azo 30 dyestufi's of very difiicultly soluble character and having little or no aflinity for textile materials, whether natural or artificial, when applied thereto in substance. Examples of such coupling components are the acidylamino coupling com- 35 ponents referred to in British Patent No. 404,363, and. other amides and substituted amides, particularly aryl-amides, of hydroxy carboxylic acids especially ortho-hydroxy carboxylic acids, of the benzene, naphthalene, carbazole and other series. 0
Mention may be made, for instance, of the anilides and naphthalides and substituted anilides or naphthalides of salicylic acid and its homologues, or of 2:3- or 1:4-oxy-naphthoic acid, for example 2:3oxy-naphthoic-ortho-toluidine or meta-nitranilide. Compounds containing more than one hydroxy carboxylic acid residue may also be used, for instance the di(2:3-oxy-naph thoyl) dianisidine... Another class of coupling component yielding difiicultly soluble dyestufls is the class of di-B-keto-acidyl derivatives of arcmatic diamines, for example the d acetoacetyl derivative of ortho-tolidine or other aromatic diamines.
As regards the shades obtainable in accordance with the invention, it is found that blue to violet shades are frequently obtained with those coupling components, such for example as 2:3-oxynaphthoic anilide or meta-nitranilide, which normally yield orange to red shades with simple diazo compounds of the benzene series. Other shades of great value may, however, be obtained. Thus with the arylamides of hydroxy carbazole carboxylic acids or with m-hydroxy-diphenylamine and the special anthraquinone diazo components, valuable brown shades of good iastness properties may be obtained.
Incoloring textile materials in accordance with the new azoic process, various modes of working may be adopted. Thus the materials impregnated with the coupling components may be treated with solutions of the diazo compounds. Again, the diazo component may be applied first, diazotized on the material and the latter thereafter subjected to the action of the coupling component. Another method of operation consists in applying both the diazo component and the coupling component to the materials, either together or separately and thereafter subjecting the materials to treatment adapted to effect diazotization of the diazo component and coupling with the coupling component.
The new processes may be utilized either for the uniform or for the local coloration of materials. In the former case the components may be applied by dyeing methods, or, if desired, by mechanical impregnation, for instance by padding or by all-over printing. For the production of local colorations, printing, stencilling or any other desired means may be employed, whether the components are applied together or separately or whether diazotization is effected on the material or in a separate operation.
or in the manner described in U. S. Patent No. 1,986,883 in the case of aceto-acetic arylide coupling components. In general the most satisfactory method, both from the point of view of the results obtained and from the point of view of simplicity, is to apply the diazo component and coupling component simultaneously in the form of aqueous dispersions, the ,diazotization and coupling being subsequently effected by treatment first in a bath containing sodium nitrite and acetic or other acid followed by treatment with a. weakly alkaline solution.
The dispersions of the diazo or coupling components may be obtained by any desired method, for. example by fine milling or grinding with or without the aid of dispersators and/or protective colloids, by precipitation in the presence of protective colloids, or by a simple treatment with dispersators, as described for instance in any of U. S. Patents Nos. 1,618,413, 1,618,414, 1,694,413, 1,690,481, 1,803,008, 1,840,572, 1,716,721, 1,928,647 and 1,959,352. In some cases the dispersion of the coupling component may be facilitated by the presence of small quantities of alkali, for
example a quantity of caustic soda sufllcient to' yield a preparation of about pH 8 to 9 or even slightly more alkaline.
In treating cellulose ester and ether materials the absorption of either or both components may be facilitated if desired by incorporating swelling agents in the dyeing or padding liquors or printing pastes employed, or the materials may be pretreated with swelling agentsm Alcohol is particularly suitable for this purpose, though other swelling agents may be employed if desired.
The following table shows a few of the numerous shades obtainable: on cellulose acetate in accordance with the invention:
in general most convenient to apply first the coupling component in the form of an alkali metal salt, for instance by a paddingirea'tment. The impregnated material is thereafter developed in a solution of the desired diazo compound, or such a solution, if necessary suitably thickened, applied by printing or other mode of local application, where localized color efiects are required.
In the case of cellulose acetate or other cellulose ester or ether materials, it is in general found most advantageous to apply coupling components inthe free state, for instance in the manner described in U. 3. Patent No. 1,844,350 in the case of arylamides of oxynaphthoic acids,
Shade on cellulose A]: ine Developer acetate 1 Full violet.
2 Sage green.
3 Bluish violet.
4 Do Sage green rather brighter than No. 2.
6 Do Yellowish sage.
7 l ammo-i-pa Phenol Puce.
8 Do- Phenyl-methyl-pyrazolone Olive.
9 Do- Meta-phenylene-diamine. Deep yellow. 10 Do b-oxy-naphthoic acid Violet. 11 Do b-naphthol Do. 12 1-amino-4-phenyl- S-oXy-anth quinone Resorcin Brownish grey. a 13 n Meta-hydroxy-diphe11ylamine Nigger brown. i4 1-amino-4-phenyl'amino-anthraqulnone do 0. 15 Do Naphthol AS] LB Chocolate brown.
As will be appreciated from the foregoing description, this invention is of especial value in connection with the coloration of cellulose ester and ether materials. In addition to cellulose acetate the invention may be applied to cellulose formate, propionate or butyrate or ethyl or benzyl cellulose materials. Other materials may also be colored by the new process, for instance wool, silk and other animal fibres, also mixed materials of all kinds, for instance materials containing both animal and vegetable fibres or materials containing cellulose acetate or other artificial fibres in conjunction with cotton or other natural fibres. In the case of animal fibres the coupling components are preferably applied from very weakly alkaline baths, or even in the form of dispersions of the free compounds; in fact the methods specified as suitable for the treatment of cellulose ester and ether materials may in general be applied with satisfaction for the coloration of animal fibres.
The following example illustrates the invention but is in no way limitative:-
Example To dye 10 kilogrammes of cellulose acetate yarn a full nigger brown of good fastness to water, 100 grammes of 1 amino 4 paratolylamino-E-hydroXy-anthraquinone are dispersed by boiling with 300 grammes of Turkey red oil and diluting with about 10 litres of hot soft water, and added to a dyebath of 300 litres of soft water. The yarn is entered and worked in this bath for two hours; duringthe first half-hour the temperature being raised to 70 C. and maintained at this temperature for the remainder of the dyeing period. The yarn is then liftedand entered into a diazotizing bath containing 6 grammes per litre sodium nitrite and 12 cos. per litre of hydrochloric acid Twad. and turned in this bath for half an hour at 25 C. After rinsing, the yarn is entered cold into 300 litres of soft water to which has been added 100 grammes of metahydroXy-diphenylamine previously dissolved in boiling water. The yarn is worked in this bath for half an hour cold,
' 150 grammes of soap added and the temperature then raised gradually .to 75 C. The yarn is turned at 75 C. for half an hour, and then soaped for a further half hour in a fresh soap bath of similar length and concentration, and is finally lifted, rinsed and dried or otherwise treated.
In the appended claims the term organic derivative of cellulose connotes a cellulose ester of an organic acid or a cellulose ether.
What we claim and desire to secure by Letters Patent is:
1. Process for the coloration of textile materials, which comprises coupling thereon an azo coupling component, said component being one which couples in an aryl residue, with a diazo compound obtainable by diazotizing a compound. selected from the group consisting of l-amino- 4-mono-alkylamino-anthraquinones, l-amino dmono-arylamino-anthraquinones, and l-amino- -mono-aralkylamino-anthraquinones.
2. Process for the coloration of organic derivative of cellulose textile materials, which comprises coupling thereon an azo coupling component, said 1 component being one which couples in an aryl residue, with a diazo compound obtainable by di azotizing a compound selected from the group consisting of 1-aminol-mono-allrylamino-anthraquinones, 1 amino-4-mono-arylamino-anthraquinones, and 1 amino 4 mono-arallrylamino 4 mono arylamino-anthraquincnes, and l-aminol-mono aralkylamino-anthraquinones.
4-. Process for the coloration of textile materials, which comprises coupling thereon a phenolic coupling component with a diazo compound obtainable by diazotizing a compound selected from the group consisting of l-arnino-t-mono-alkylamino-anthraquinones, l-amino l mono-arylamino anthraquinones, and 1 -amino l -monoaralkylamino-anthraquinones.
5. Process for the coloration of textileniaterials, which comprises coupling thereon an arylamide of an. aromatic hydroxy carboxylic acid with a diazo compound obtainable by diazotizing a l-amino-4-mono-arylamino-anthraquinone.
6. Process for the coloration of cellulose acetate textile materials, which comprises coupling thereon an arylamide of an aromatic hydroxy carboxylic acid with a diazo compound obtainable by diazotizing a 1-amino-4-mono-arylamino-anthraquinone.
7. Process for the coloration of textile materials, which comprises coupling thereon an arylamide of 2:3-oxy-naphthoic acid with a diazo compound obtainable by diazotizing a 1-arninol-mono-arylaminoanthrawpuinone.
8. Process for the coloration of cellulose acetate textile materials, which comprises coupling thereon an arylamide of 2:3-oxy-naphthoic acid with a diazo compound obtainable by diazotizing a 1- amino-4-mono-arylamino-anthraquinone.
9. Process for the coloration of textile materials, which comprises coupling thereon meta-hydroxy-diphenylamine with a diazo compound obtainable .by diazotizing a 1-arnino-4=-mono-arylamino-anthraquino-ne.
10. Process for the coloration of cellulose acetate textile materials, which comprises coupling thereon metahydroxy-diphenylamine with a diazo compound obtainable by diazotizing a1- amino-a-mono-arylarnino-anthraquinone.
11. Process for the coloration of textile materials, which comprises coupling thereon resorcinol with a diazo compound obtainable by diazotizing a 1-amino l-mono-arylamino-anthraquinone.
12. Process for the coloration of cellulose acetate textile materials, which comprises coupling thereon resorcinol with a diazo compound obtainable by diazotizing a l-aminol-monoarylamino-anthraquinone.
13. Process for the coloration of cellulose acetate textile materials, which comprises coupling thereon meta-hydroxy-diphenylamine with a diazo compound obtainable by diazotizing 1- amino--phenylarnino-anthraquinone.
14. Textile materials colored with an azo dyestuff obtainable by coupling an arylamide of a hydrorry carboxylic acid with a diazo compound obtainable by diazotizing a 1-amino-4-mon0- arylamino-anthraquinone.
15. Cellulose acetate textile materials colored with an azo dyestuif obtainable by coupling metahydroxy-diphenylamine with a diazo compound obtainable by diazotizing a l-aminol-monoarylamino-anthraquinone.
l6. Cellulose acetate textile materials colored with an 9.20 dyestuif obtainable by coupling metahydroxy-diphenylamine with a diazo compound obtainable by diazotizing l amino-d-phenylamino anthraquinone;
GEORGE HOLLAND ELLIS. ERNEST VI'ILLIAM KIRK.
US44558A 1932-10-06 1935-10-11 Coloration of textile materials Expired - Lifetime US2112276A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101975A1 (en) * 1982-08-12 1984-03-07 BASF Aktiengesellschaft Pigment dyestuffs of the pyrazolone series

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0101975A1 (en) * 1982-08-12 1984-03-07 BASF Aktiengesellschaft Pigment dyestuffs of the pyrazolone series
US4563519A (en) * 1982-08-12 1986-01-07 Basf Aktiengesellschaft Anthraquinone azopyrazalone colorants

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