WO1999023172A1 - Compositions de pigments a stockage thermique stabilise renfermant de la colophane ayant subi une dismutation et une fumaration ou une maleination - Google Patents

Compositions de pigments a stockage thermique stabilise renfermant de la colophane ayant subi une dismutation et une fumaration ou une maleination Download PDF

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Publication number
WO1999023172A1
WO1999023172A1 PCT/US1997/019805 US9719805W WO9923172A1 WO 1999023172 A1 WO1999023172 A1 WO 1999023172A1 US 9719805 W US9719805 W US 9719805W WO 9923172 A1 WO9923172 A1 WO 9923172A1
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WO
WIPO (PCT)
Prior art keywords
pigment
rosin
pigment composition
fumarated
composition
Prior art date
Application number
PCT/US1997/019805
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English (en)
Inventor
Arne Vinther
Steffen C. Olsen
Knud R. BJØRNSON
Original Assignee
Sun Chemical Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Sun Chemical Corporation filed Critical Sun Chemical Corporation
Priority to PCT/US1997/019805 priority Critical patent/WO1999023172A1/fr
Publication of WO1999023172A1 publication Critical patent/WO1999023172A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0009—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives
    • C09B67/001—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives containing resinic acid derivatives

Definitions

  • the present invention relates to pigment compositions comprising disproportionated and fumarated or aleinated rosin, and which have improved thermal storage stability.
  • the present invention also relates to the preparation and use of such pigment compositions, as well as to pigment pastes comprising such pigment compositions.
  • rosinated pigments have led to development of rosinated pigments.
  • the incorporation of natural rosin and rosin derivatives into pigments is desirable in order to optimize and balance the properties of the pigment such as color strength, ease of dispersion and transparency.
  • the mean particle size of the color component needs to be very small, and as a consequence the rosin, which is believed to coat the individual color particles, has a high surface area which, in the case of dry pigments, is exposed to air.
  • These products therefore are prone to self-heating even at temperatures used in manufacture and storage.
  • a result of this combination of instability in air and high surface area is that the products have a tendency to decompose slowly on storage which leads to self-heating and eventually under special conditions may result in ignition.
  • European Patent 0671443 Al describes one method for reducing the tendency of a rosinated pigment product to self-heat, wherein a multi-valent metal or metalloid is used.
  • the invention relates to pigment compositions having a reduced tendency to self-heat, and which furthermore have excellent physical and colouristic properties comprising an organic pigment and a rosin derivative, wherein the rosin derivative has a partially maleinated or fumarated and disproportionated rosin.
  • Figure 1 illustrates the results of a self-heating test for Pigment Yellow 13 without rosin as prepared in Example 3.
  • Figure 2 illustrates the results of a self-heating test for Pigment Yellow 13 with Resin 731D ® as prepared in Example 4.
  • Figure 3 illustrates the results of a self-heating test for Pigment Yellow 13 with Recol ® as prepared in Example 5.
  • Figure 4 illustrates the results of a self-heating test for Pigment Yellow 13 with Recol ® as prepared in Example 1.
  • Figure 5 illustrates the results of a self-heating test for Pigment Red 57:1 with Recol ® as prepared in Example 8.
  • Figure 6 illustrates the results of a self-heating test for Pigment Blue 15:3 with Recol ® as prepared in Example 6.
  • Fumarated or maleinated rosins give very good colouristic properties when used in pigments. It is believed that fully maleinated/fumarated rosins should be substantially unable to self-heat. However, the softening point of such rosin qualities would be to high for practical applications in the pigment industry. It has now been found that if the rosin derivative is only partially maleinated/fumarated and at the same time is disproportionated, it is possible to obtain products that give good colouristic properties and have a greatly reduced tendency to self-heat.
  • partially maleinated/fumarated used in conjunction with rosin derivative, means a rosin derivative modified so that 1-25 wt.%, and more preferably 2-20 wt.%, and even more preferably 3-15 wt.%, of the rosin derivative comprises maleic acid, maleic anhydride, and/or fumaric acid moieties .
  • Maleination and fumaration of natural or modified rosin is performed by methods known to persons of ordinary skill in the art, e.g.
  • rosin the levopimaric acid constituent of natural or modified rosin, or isomeric constituents which can isomerise to levopimaric acid at elevated temperatures, e.g. abietic acid, palustric acid and neoabietic acid and maleic acid, maleic anhydride, and/or fumaric acid.
  • abietic acid e.g. abietic acid, palustric acid and neoabietic acid and maleic acid
  • maleic anhydride e.g. abietic acid, palustric acid and neoabietic acid and maleic acid, maleic anhydride, and/or fumaric acid.
  • a mixture of maleic acid, maleic anhydride and fumaric acid can be used to obtain a mixed product.
  • disproportionated used in conjunction with rosin, means that at least some of the rosin constituents (which typically comprise two (conjugated) double bonds; e.g.
  • abietic acid, levopimaric acid, neoabietic acid and palastric acid have been treated under catalytic conditions to yield rosin constituents having no double bonds or only single non- conjugated double bonds and rosin constituents having an aromatic ring.
  • Disproportionation may be obtained by heating a natural or modified rosin under catalytic conditions known to a person of ordinary skill in the art.
  • the degree of disproportionation is so that the content of abietic acid-type constituents a range of from 0-50 wt.%, preferably 0-40 wt.%, more preferably 0-30 wt.% and most preferably 0-20 wt.%.
  • the term "abietic acid-type constituents” refers to constituents having two conjugated or non-conjugated double bonds. Examples of abietic acid-type constituents are albietic acid, levopimaric acid, neoabietic acid, palustric acid, pimaric acid, iso-pimaric acid, sandaracopimaric acid and elliotinoic acid.
  • the rosin in question comprises 1-25 wt.%, more preferably 2-20 wt.% of constituents carrying maleic acid, maleic anhydride, and/or fumaric acid moieties, while at the same time comprising 0-50 wt.% of abietic acid-type constituents.
  • the pigment compositions of the present invention preferably contain a rosin derivative comprising at least 2 wt.%, and preferably at least 3 wt.%, rosin constituents which include an anhydride moiety. Such rosin constituents may arise from maleination, e.g. formation of the maleic anhydride modified rosin constituent.
  • the rosin quality i.e. the partially maleinated/fumarated and disproportionated rosin, may be obtained from a natural rosin or modified rosin.
  • the rosin derivatives included in the pigment compositions of the present invention comprise natural or modified rosins which have been partially maleinated or fumarated and subsequently disproportionated.
  • the natural or modified rosins may be disproportionated prior to maleination or fumaration.
  • maleination/fumaration is performed prior to disproportionation.
  • rosin qualities are commercially available. Examples hereof are wood rosin, gum rosin and tall oil rosin. Furthermore, a wide range of modified rosin qualities are also available, e.g. natural rosins which have been chemically modified by for example hydrogenation, disproportionation, polymerisation, maleination, fumaration and esterification.
  • rosin constituent refers to all of the individual chemical compounds (having the abietic acid skeleton or modifications thereof) found in natural and modified rosin qualities.
  • rosin constituents are abietic acid, levopimaric acid, neoabietic acid, palustric acid, pimaric acid, isopimaric acid, dihydroabietic acid, tetrahydroabietic acid, sandaracopimaric acid, dehydroabietic acid and elliotinoic acid.
  • the rosin derivative used in the pigment compositions of the present invention comprises as an important feature the maleinated/fumarated rosin and disproportionated rosin constituents as defined above.
  • the amount of rosin derivative is supplemented with an amount of natural or modified rosins not having the special features of the rosin derivative defined above, the amount of rosin constituents carrying maleic acid, maleic anhydride, and/or fumaric acid moieties, and the amount of abietic acid-type constituents, should, relative to the total content of rosin derivative and natural or modified rosin, still be within the defined limits.
  • natural or modified rosins supplements should be construed as being included in the meaning of rosin derivatives .
  • the rosin derivatives should preferably have a softening point ranging from 80-120°C and more preferably from 80-100°C.
  • the rosinated pigment composition of the present invention may comprise further constituents such as one or more additives which may be supplied to the pigment, pigment dispersion or product before or after drying.
  • additives include surfactants, such as long chain fatty acids and derivatives thereof, alcohols, and amines.
  • Further additives which may be added the pigment include water soluble dyestuffs.
  • the surfactants used may be of the anionic type, such as fatty acids taurides, fatty acid N-methyltaurides, fatty acid isothionates, alkylbenzenesulphonates, alkylnaphthalene-sulphoneates, alkylphenol, polyglycol ether sulphates and fatty alcohol polyglycol ether sulphates; fatty acids, such as palmitic, stearic and oleic acids; soaps such as alkali metal salts of fatty acids and naphthenic acids; cationic surfactants including quaternary ammonium salts, and N-oxides of tertiary amines or salts thereof; and non- ionic surfactants including fatty alcohol polyglycol ethers (ethoxylated fatty alcohols) , fatty acid polyglycol ester, alkylphenol polyglycol ethers and dialkyl polyglycol ethers.
  • anionic type such as fatty acids tau
  • the alcohols used may be aliphatic alcohols, long chain primary alcohols such as stearly, oleyl or cetyl alcohols or mixtures of alcohols.
  • the amines used may be aliphatic amines which may be added include long chain primary amines e.g. stearylamine; amine derivatives of wood rosin; N-long chain alkylalkylene diamines, polyamines, betaamines, polyamide/polyamine derivatives of ethoxylated fatty amines and diamines, and derivatives of these compounds.
  • the pigment compositions comprise 55-98 wt.%, and more preferably 60-98 wt.%, of one or more organic pigments, 2-45 wt.% and more preferably 2-40 wt.% of a rosin derivative comprising a partially maleinated/fumarated and disproportionated rosin and optionally one or more additives.
  • the organic pigment may, for example, be selected from phthalocyanines, perinones, quinacridones, indanthrones, flavanthrones, pyranthrones, perylenes, thioindigos, dioxazines, isoindolines, diketopyrrolopyrroles, basic dye complexes, metal complexes, monoazo pigments, azo metal salts, and disazo pigments.
  • a disazo pigment e.g. a diarylide pigment of the formula:
  • Ar 1 and Ar 2 are phenyl groups which independently may be optionally substituted by one, two or three substituents selected from halogen (preferably chlorine) , methyl, and methoxy.
  • Ar 1 and Ar 2 are independently selected from phenyl, 2, 4-dimethylphenyl, 2-methylphenyl, 4-chloro-2, 5-dimethylphenyl .
  • the invention is also particularly useful where the organic pigment is an azo metal salt of the formula:
  • M 2+ is a metal ion, preferably calcium, barium or strontium
  • R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, halogen (preferably chlorine), and methyl.
  • halogen preferably chlorine
  • R 1 , R 2 , R 3 , and R 4 are different from hydrogen.
  • the present invention is also believed to be particularly useful for phthalocyanine pigments, of the formula:
  • Me is a metal such as copper, nickel, or cobalt, while preferred is copper.
  • the invention further provides a method for preparing a pigment composition having one or more organic pigments and rosin derivative wherein the method comprises contacting an aqueous dispersion of the organic organic pigments and rosin derivative wherein the method comprises contacting an aqueous dispersion of the organic pigment (s) with a solution or dispersion of rosin derivative and wherein the rosin derivatives comprise (s) a partially maleinated/fumarated and disproportionate rosin.
  • the organic pigments are typically synthesized as a dispersion in an aqueous medium.
  • the rosin derivatives are preferably added to the aqueous dispersion in the form of a dispersion or solution, preferably in an alkaline solution as the corresponding basic salt, e.g. the alkali metal salt such as the sodium salt prepared from the rosin component (comprising a free carboxylic acid group) and sodium hydroxide
  • the solution or dispersion of the rosin derivatives is added to the dispersion of the organic pigment. It should be understood that the contacting process is equally applicable in the case where the dispersion of the organic pigment is added to the dispersion/solution of the rosin derivatives) .
  • the resulting mixture (also a dispersion) is preferably kept at an elevated temperature, preferably in the range of 50-120°C, for up to 24 hours, and then acidified or laked, for example, with a calcium salt form to sparingly soluble calcium salt in order to precipitate the pigment composition.
  • the product of the present invention may be isolated by any conventional technique, e.g. using a filter press or band filter.
  • the isolated pigment composition is optionally washed and dried, e.g. in an oven such as a conventional or microwave oven, or by a non-static technique, e.g. by spray drying or in a fluidised bed. Since the pigment compositions obtained by the present invention have a reduced tendency to self-heat, they can be dried at higher temperatures than are normally used for pigment drying. This also means that they can be dried faster which can lead to increased throughput in pigment manufacturing.
  • the reduction in the tendency of the pigment composition to self-heat, achieved by the present invention is particular useful in surface coating compositions such as paints or printing inks or in high molecular weight materials that employ the pigment.
  • the pigment compositions of the invention have a high degree of compatibility with conventional surface coatings, especially printing inks, resulting in improved ease of incorporation and dispersibility, color strength, transparency and gloss, relative to surface coating media produced using conventional means.
  • the present invention is ideal for providing pigments for plastic or textile use.
  • the pigment compositions of the present invention are preferably in the form of a powder or a press cake.
  • the pigment compositions when tested in the self-heating test (10x10x10) at a temperature of at least 120°C, resulted in no self- heating.
  • a temperature of 130°C or higher, or even at a temperature of 140°C or higher, in the self-heating test should result in no self-heating.
  • the present invention provides for pigment compositions of:
  • the pigment composition has been self heating tested at temperatures of at least 120°C and resulted in no self-heating.
  • the pigment compositions according to the present invention are intended to solve the problem associated with the self-heating of dry pigment compositions, the excellent transparency properties of the pigment compositions make them equally applicable for other formulations.
  • one particularly interesting use of the pigment compositions of the invention are in formulations obtained using the so-called "flush” technique.
  • the underlying principle in the flush technique is that an organic pigment (here associated with rosin derivatives, and optionally with additives) which has a greater affinity for an oil phase than for an aqueous phase (e.g. the aqueous phase in which the organic pigment is synthesized) can be transferred from ' the aqueous phase into an appropriate oil phase, thereby forming a pigment paste comprising the pigment composition.
  • the "dry flush" technique where granules or lumps of the dry pigment composition is used may also be applied.
  • the use of the flushing technique avoids certain problems, e.g. prolonged drying times, grinding treatment and dusting, associated with conventional pigment powder production methods .
  • the present invention also relates to a pigment paste comprising the pigment compositions herein together with one or more components such as components selected from alkyds, varnished, and mineral oils.
  • Other useful components are known to persons of ordinary skill in the art and are described in detail by Herbst, W. and Hunger, K., Industrielle Organische Pigmente, VCH; Gomm, A.S. et al., J. Oil Color Chem. Assoc, 51, 5 (1968), pp.
  • the pigment pastes according to the present invention are especially useful for the preparation of an ink.
  • the following examples illustrate specific aspects of the present invention and are not intended to limit the scope thereof in any respect and should not be so construed.
  • Solution A A slurry of 25 g 3, 3 ' -dichlorobenzidine bishydrochloride in 50 mL 30 vol.% hydrochloric acid and 100 mL of water was cooled to 0 °C and a solution of 14.2 g sodium nitrite in 25 mL of water was added. The surplus of sodium nitrite was removed with the help of sulfamic acid.
  • Solution B 45.3 g acetoacet-m-xylidide dissolved in 30 mL 28 vol.% sodium hydroxide and 200 mL water was acidified by addition of a solution of 8.0 mL acetic acid and 15.5 mL 30% hydrochloric acid in 80 mL of water during 15 minutes. The pH was adjusted to 8.5-9.0 and the temperature to 20 °C. 0.9 g 2, 2 ' -benzidinedisulfonic acid was diazotised as above under A using sodium nitrite and was added to Solution B.
  • the pigment press cake was made according to Example 1, except that instead of the 45.3 g acetoacet-m-xylidide used in Solution B, a mixture of 32 g acetoacet-m- xylidide and 12.5 g acetoacet-o-toluidide was used.
  • the pigment press cake was made according to Example 1 with the exception that no rosin was used.
  • the pigment press cake was made according to Example 1 with the exception that the rosin used was Resin 731D ® .
  • the pigment press cake was made according to Example 1 with the exception that the rosin used was Recol ® F-10.
  • Example 6 Preparation of Pigment Yellow 13 with Recol ® F-3 and Resin 731D ®
  • the pigment press cake was made according to Example 1.
  • rosin used was a mixture of Recol ® F-3 and Resin 731D ® in a 1:1 ratio.
  • the pigment press cake was made according to Example 1.
  • rosin used was a mixture of Recol ® F-3 and Resin 731D ® in a 1:1 ratio.
  • Example 9 Preparation of Pigment Blue 15:3 with Recol ® F-3
  • a dough mixer was preheated to 80°C. 2800 g sodium chloride, 800 g of Blue Crude No 4s, 120 g of Recol ® F-3, 28 mL of sodium hydroxide and 208 g of calcium chloride were added to the mixer. 2800 g of sodium chloride was added together with 320 mL of diethyleneglycol . The product was mixed for several hours at 80°C. After mixing, the product was transferred to a bucket and 40000 L of water was added. The temperature was set to 80°C and pH was adjusted to 1. After 2 hours the product was filtered, washed and dried.
  • the washed press cake made according to Examples 1-9 may either be used as such (e.g. as in Example 10) or may be dried prior to use (e.g. as in Example 11) .
  • Example 10 Each of the dried press cakes produced according to Examples 1-2 and 4-7 were transferred to the flush machine and alkyd and varnish was added, see Example 10. After the pigments were fully dispersed, the concentrated pigment pastes were transformed into an ink. When compared to the inks made from Pigment Yellow 13, mixtures of Pigment Yellow 13 and Pigment Yellow 174 and Pigment Red 57:1 containing Resin 731D ® , inks prepared with the flushed pigment pastes containing Recol ® F-3 had much higher color strength measured colormetrically.
  • the assessment of the thermal storage stability was carried out at an elevated temperature (e.g. at 120°C) which results in acceleration of the decomposition and greater ease of measurement.
  • Decomposition at elevated temperature is indicative for the tendency for a pigment composition to self-heat at temperatures normally used for storage.
  • Fine mesh basket made of stainless steel in the shape of a cube of size 1000 mL was packed with dry milled product with gentle tapping.
  • the basket was placed in the middle of another net of side lengths 15 cm and height 25 cm, to reduce cooling.
  • a thermocouple was then placed in the middle of the pigment mass, and the temperature recorded by computer.
  • the pigment composition sample (dried and pulverised) and nets were placed in a thermostatic air oven held at 120 °C and the temperature in the center of the pigment was recorded throughout the heating period. The heating period was not less than 24 hours, unless the temperature in the center of the pigment exceeded 200°C during this period.
  • the results for pigment compositions tested in the self-heating test as described above i.e. center temperature ⁇ y-axis> versus time ⁇ x-axis>) are shown in Figures 1-6.
  • emulsion A showed that the anhydride was degraded to acid as there only was absorption at the COO ' region of the spectrum.
  • product A showed no anhydride absorption, but large absorption for COO " .
  • product B showed traces of anhydride.
  • Example 9 modified to 36 mL of 28% sodium hydroxide and 200 mL of water.
  • the solution was cooled to 20°C and crystallized by adding hydrochloric acid until pH below 0.
  • the crystals were broken into small pieces and washed with water, then dried in an oven at 95°C for 12 hours.
  • the rosin mass was cooled to 20°C.
  • An IR spectrum was recorded. Comparison of the IR spectra of the starting material Recol ® F-3 and the treated material showed no significant differences.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)

Abstract

Cette composition de pigments renfermant un pigment organique, sinon plusieurs, et un dérivé de la colophane, consistant en de la colophane ayant subi une dismutation et une fumaration ou une maléination, fait montre de caractéristiques améliorées de stockage thermique.
PCT/US1997/019805 1997-10-30 1997-10-30 Compositions de pigments a stockage thermique stabilise renfermant de la colophane ayant subi une dismutation et une fumaration ou une maleination WO1999023172A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1997/019805 WO1999023172A1 (fr) 1997-10-30 1997-10-30 Compositions de pigments a stockage thermique stabilise renfermant de la colophane ayant subi une dismutation et une fumaration ou une maleination

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PCT/US1997/019805 WO1999023172A1 (fr) 1997-10-30 1997-10-30 Compositions de pigments a stockage thermique stabilise renfermant de la colophane ayant subi une dismutation et une fumaration ou une maleination

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002070611A2 (fr) * 2001-03-06 2002-09-12 Clariant Gmbh Preparations de pigments de jaune de diaryle
US7722715B2 (en) * 2004-04-06 2010-05-25 Ciba Specialty Chemicals Corporation Pigment compositions for inks with improved rheology
US8034174B2 (en) * 2008-04-18 2011-10-11 Sun Chemical Corporation Diarylide yellow pigments
CN102732052A (zh) * 2012-05-29 2012-10-17 吴江市屯村颜料厂 一种3120耐晒艳红bbc的制备方法
CN113462189A (zh) * 2021-06-25 2021-10-01 杭州映山花颜料化工有限公司 一种偶氮颜料的制备方法

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Publication number Priority date Publication date Assignee Title
CH397925A (fr) * 1959-02-26 1965-08-31 Kuhlmann Ets Procédé pour l'amélioration du brillant spéculaire des pigments
FR2409292A1 (fr) * 1977-11-18 1979-06-15 Ciba Geigy Ag Procede de preparation de compositions de pigments ne formant pas de poussiere
EP0050313A1 (fr) * 1980-10-21 1982-04-28 Hoechst Aktiengesellschaft Procédé de fabrication de granulés de pigment et leur utilisation
JPS5959760A (ja) * 1982-09-29 1984-04-05 Harima Kasei Kogyo Kk 光硬化性樹脂
EP0665272A1 (fr) * 1994-01-25 1995-08-02 Ciba-Geigy Ag 2,9-diméthylquinacridone traitée par une résine
EP0671443A1 (fr) * 1994-03-04 1995-09-13 Ciba-Geigy Ag Compositions de pigments traités de résines

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH397925A (fr) * 1959-02-26 1965-08-31 Kuhlmann Ets Procédé pour l'amélioration du brillant spéculaire des pigments
FR2409292A1 (fr) * 1977-11-18 1979-06-15 Ciba Geigy Ag Procede de preparation de compositions de pigments ne formant pas de poussiere
EP0050313A1 (fr) * 1980-10-21 1982-04-28 Hoechst Aktiengesellschaft Procédé de fabrication de granulés de pigment et leur utilisation
JPS5959760A (ja) * 1982-09-29 1984-04-05 Harima Kasei Kogyo Kk 光硬化性樹脂
EP0665272A1 (fr) * 1994-01-25 1995-08-02 Ciba-Geigy Ag 2,9-diméthylquinacridone traitée par une résine
EP0671443A1 (fr) * 1994-03-04 1995-09-13 Ciba-Geigy Ag Compositions de pigments traités de résines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 008, no. 156 (C - 234) 19 July 1984 (1984-07-19) *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002070611A2 (fr) * 2001-03-06 2002-09-12 Clariant Gmbh Preparations de pigments de jaune de diaryle
WO2002070611A3 (fr) * 2001-03-06 2002-12-27 Clariant Gmbh Preparations de pigments de jaune de diaryle
US7118623B2 (en) 2001-03-06 2006-10-10 Clariant Gmbh Diaryl yellow pigment preparations
KR100845930B1 (ko) * 2001-03-06 2008-07-11 클라리안트 프로두크테 (도이칠란트) 게엠베하 디아릴 황색 안료 제제
US7722715B2 (en) * 2004-04-06 2010-05-25 Ciba Specialty Chemicals Corporation Pigment compositions for inks with improved rheology
US8034174B2 (en) * 2008-04-18 2011-10-11 Sun Chemical Corporation Diarylide yellow pigments
CN102732052A (zh) * 2012-05-29 2012-10-17 吴江市屯村颜料厂 一种3120耐晒艳红bbc的制备方法
CN113462189A (zh) * 2021-06-25 2021-10-01 杭州映山花颜料化工有限公司 一种偶氮颜料的制备方法
CN113462189B (zh) * 2021-06-25 2023-04-25 杭州映山花颜料化工有限公司 一种偶氮颜料的制备方法

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