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WO2011078502A2 - Dérivés pigmentaires contenant du pyrazole destinés à afficher des filtres colorés - Google Patents

Dérivés pigmentaires contenant du pyrazole destinés à afficher des filtres colorés Download PDF

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Publication number
WO2011078502A2
WO2011078502A2 PCT/KR2010/008786 KR2010008786W WO2011078502A2 WO 2011078502 A2 WO2011078502 A2 WO 2011078502A2 KR 2010008786 W KR2010008786 W KR 2010008786W WO 2011078502 A2 WO2011078502 A2 WO 2011078502A2
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Prior art keywords
pigment
pigment composition
weight
formula
parts
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2010/008786
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English (en)
Korean (ko)
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WO2011078502A3 (fr
Inventor
박순현
김고현
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Kyung In Synthetic Corp
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Kyung In Synthetic Corp
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
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Publication of WO2011078502A2 publication Critical patent/WO2011078502A2/fr
Publication of WO2011078502A3 publication Critical patent/WO2011078502A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
    • C09B47/16—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by nitrogen atoms
    • 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
    • C09B49/00—Sulfur dyes
    • 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
    • C09B19/00—Oxazine dyes
    • C09B19/02—Bisoxazines prepared from aminoquinones
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • 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
    • C09B49/00—Sulfur dyes
    • C09B49/06—Sulfur dyes from azines, oxazines, thiazines or thiazoles
    • 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
    • C09B55/00—Azomethine dyes
    • C09B55/001—Azomethine dyes forming a 1,2 complex metal compound, e.g. with Co or Cr, with an other dye, e.g. with an azo or azomethine dye
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes

Definitions

  • the present invention relates to pigments for color filters in liquid crystal displays, characterized in that it comprises a pyrazole-containing pigment derivative, and which relates to pigment compositions which exhibit improved color properties and exhibit excellent stability and dispersibility properties.
  • Pigment compositions have been used in inks, paints, and the like, but with the recent development of IT technology, they are widely used as color filters.
  • Such color filters are mainly used in liquid crystal displays, screens, color separation devices and sensors, and are well known examples of LCD monitors or TVs.
  • Color can be added by Regarding the aforementioned methods, both a method of directly generating a pixel pattern by printing and an indirect photolithography generation method are important, and in particular, in the above-described pigment dispersion method, a photolithography generation method is important.
  • the pigment dispersion method technique of "non-photosensitive polyimide method form" is disclosed in Japanese Patent Application Laid-Open No. 1998-22392 or the like.
  • the use of pigments has the advantage that the color filter's resistance to light, moisture and heat is improved compared to dye-based coating systems.
  • the transparency and color purity of the pigment-based coatings are unsatisfactory regardless of the coating method, and in particular, incorporating various mixed pigments into the photoresist to match the desired color trajectory values involves unwanted brightness and transparency loss. As a result, energy requirements for LCDs and the like are increased.
  • European Patent Application Publication No. 1489143 discloses at least one compound of ammonium salts of aminomethyl substituted phthalocyanine, phthalimidomethyl phthalocyanine and sulfophthalocyanine.
  • the composition of copper phthalocyanine was described.
  • beta foam Cold Index Pigment Blue 15: 4 is a green color is not suitable for color filters.
  • Japanese Patent Application Laid-Open No. 1998-152141 discloses a composition comprising epsilon copper phthalocyanine, phthalimidomethyl copper phthalocyanine and sulfonated copper phthalocyanine or an alkali metal salt thereof.
  • the purpose is a pigment used for thermosetting resins, it is not suitable for color filter applications requiring transparency and contrast.
  • European Patent Application Publication No. 1130065 discloses a composition comprising epsilon copperphthalocyanine and azo or other polycyclic pigments. According to this application, it has been described that phthalocyanine derivatives of many other phthalocyanines with phthalimidomethyl and / or sulfonated groups or salts thereof may be used. However, it is not suitable for color filter applications requiring high storage stability and contrast.
  • Japanese Patent Application Laid-Open No. 2000-258620 discloses a process of salting pure alpha copper phthalocyanine obtained by an acid faceting method with a phthalocyanine derivative as a crystal stabilizer. However, since high purity epsilon phthalocyanine cannot be obtained, it is not suitable as a blue color filter.
  • Japanese Patent Application Laid-Open No. 2005-234009 discloses salt nipping of epsilon copper phthalocyanine stabilized with copper phthalocyanine sulfonamide with phthalmethylimidomethyl copper phthalocyanine, followed by washing to remove organic solvents and inorganic salts. Disclosed is a technique for surface treatment with a sulfonated copper phthalocyanine or a salt thereof. However, it is not suitable for color filters due to low epsilon purity.
  • European Patent Application Publication No. 0485337 (1990) describes pyrazole derivatives and methods of synthesis, but does not provide a use for color filters.
  • PCT International Patent Application Publication No. WO2008 / 095801 discloses phthalocyanine compositions comprising aminomethyl phthalocyanine and ammonium sulfonated phthalocyanine, but is not suitable for color filter applications requiring high storage stability and contrast.
  • the present invention aims to solve the problems of the prior art as described above and the technical problems that have been requested from the past.
  • the pigment composition for color filters according to the present invention for achieving the above object is composed of 50 to 99% of the organic pigment, and 1 to 50% by weight of the compound of the formula (1) based on the total weight :
  • Q is a pigment moiety
  • A is not particularly limited as long as it can interconnect Q and pyrazole, but preferably '-CH 2- ' or '-CH 2 -CH 2- ' Can be used.
  • M is not particularly limited as long as it can be bonded to the above position, but preferably hydrogen or a metal, and the metal may be more preferably an alkali metal or an alkaline earth metal.
  • n is an integer from 0 to 2
  • m is an integer from 1 to 4
  • R 1 to R 3 is not particularly limited, but independently of each other hydrogen, C 1 -C 6 alkyl, C 1 -C 6 aryl or OH Is preferably.
  • the present invention by including the compound of Formula 1, as will be demonstrated later in the experiment, it provides a pigment composition for a color filter with improved color characteristics such as contrast ratio and brightness and excellent storage stability.
  • the organic pigment is, for example, monoazo, diazo, lakeazo, beta nattol, natitol AS, benzimidazolone, diazo condensate, azo metal complex, isoin Polycyclic pigments such as dolline and isoindolinone compounds, or phthalocyanine, quinatridone, perylene, lerione, thioindigo, anthraquinone, dioxazine, quinophthalone and diketopyrrolopyrrole compounds have.
  • lake dyes such as Ca, Mg and Al lakes of sulfo- or carboxyl-containing dyes can also be used.
  • organic pigments include pigments of the following color index:
  • Color index pigment blue 1, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60, etc .; or
  • Organic pigments which may be particularly preferably used in the present invention are phthalocyanine and dioxazine.
  • the content of such organic pigments may be 50 to 99% based on the total weight, preferably 50 to 95% by weight, more preferably 60 to 90% by weight, as defined above.
  • a pyrazole-containing pigment derivative having a structure similar to that of formula 1 is disclosed in European Patent Application Publication No. 0485337 (1990).
  • the derivatives of the above application have a structure bonded to the pigment site via the nitrogen atom of the pyrazole ring, and thus are not only different from the compound of the formula (1), but also teach the possibility of using such a compound as a color filter. It does not imply.
  • the compound of formula 1 of the present invention is different from the disclosed material of the above application because it is bound to the pigment site via the carbon atom of the pyrazole ring.
  • the pigment composition for a color filter when constituting the pigment composition for a color filter, it exhibits more excellent physical properties in color characteristics, storage stability and the like.
  • the pigment portion (Q) may be preferably phthalocyanine, dioxazine, diketopyrrolopyrrole, or PY150.
  • R 1 to R 3 may preferably be independently of each other C 1 -C 6 alkyl, more preferably C 1 -C 4 alkyl.
  • the content of the compound of Formula 1 may be 1 to 50% by weight, preferably 1 to 40% by weight, more preferably 3 to 30% by weight, based on the total weight as defined above.
  • the pigment composition of the present invention may further include at least one ammonium sulfonato pigment and / or at least one aminoalkyl substituted pigment.
  • ammonium sulfonato pigment When the ammonium sulfonato pigment is included, its content is preferably more than 0 to 10% by weight based on the content of the total composition, and when the aminoalkyl substituted pigment is included, its content is It is preferably 5 to 15% by weight based on the content.
  • aminoalkyl substituted pigments include dimethylaminomethylphthalocyanine, methylaminomethylphthalocyanine, dimethylaminomethyldioxazine and the like.
  • the pigment composition of the present invention may further include a compound of formula (2).
  • Q ' is any pigment, preferably PY150, dioxazine, phthalocyanine or diketopyrrolopyrrole dye site, n' is an integer from 0 to 2, m 'is an integer from 1 to 4, B Is a carbonamide, sulfonamide, or phthalimide group.
  • the viscosity of the pigment composition that is, the storage stability, is improved.
  • fine color control of the functional group is possible to express a variety of colors.
  • the compound of Formula 2 may be included in 0.1 to 30% by weight based on the total weight of the pigment composition.
  • the content of the organic pigment and the compound of formula 1 is preferably maintained at 1 to 99% by weight based on the total amount of the composition. More preferred content is 5 to 80% by weight.
  • the pigment composition according to the present invention preferably has a primary particle size of less than 60 nm in a transmission electron microscope, in particular, a primary particle size of 40 nm, so that it can exhibit color properties, stability and dispersibility suitable for a color filter. It is more preferable that it is less than.
  • one or more organic solvents, binders and / or dispersants may further be included.
  • organic solvent it is a ketone, an alkylene glycol ether, an alcohol, and an aromatic compound, for example.
  • the group of ketones includes acetone, methyl ethyl ketone, cyclohexanone and the like
  • the group of alkylene glycol ethers includes methyl cellosolve (ethylene glycol monomethyl ether), butyl cellosolve (ethylene glycol monobutyl ether), methyl cell Rosolbe acetate, ethylcellosolvebe acetate, butylcellosolvebe acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl Ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono
  • solvents include 1,2-propanediol diacetate, 3-methyl-3-methoxybutyl acetate, ethyl acetate, tetrahydrofuran and the like. These solvents may be used alone or in mixture with each other.
  • the binder is not particularly limited as long as it is a resin capable of exhibiting binding force, and particularly known film-forming resins are useful.
  • cellulose resins especially carboxymethylhydroxyethyl cellulose and hydroxyethyl cellulose, acrylic acid resins, alkyd resins, melamine resins, epoxy resins, polyvinyl alcohols, polyvinylpyrrolidones, polyamides, polyamide-imines, Polyimide resins are useful.
  • Useful binders include resins having photopolymerizable unsaturated bonds, and can be, for example, binders in the acrylic acid resin group.
  • polymerizable monomers such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, styrene and styrene derivatives, (meth Carboxyl-containing polymerizable monomers such as acrylic acid, itaconic acid, maleic acid, maleic anhydride, monoalkyl maleates (particularly alkyl having 1 to 12 carbon atoms), and (meth) acrylic acid, styrene and styrene derivatives (eg copolymers between polymerizable monomers such as (alpha) -methylstyrene, m- or p-methoxystyrene, p-hydroxystyrene) are useful
  • Examples include compounds containing an oxirane ring and an ethylenically unsaturated compound, for example, glycidyl (meth) acrylate, acryloyl glycidyl ether and monoalkylglycidyl itaconate, and the like. Reaction products of carboxyl-containing polymerized compounds, and compounds containing hydroxyl groups and ethylenically unsaturated compounds (unsaturated alcohols), respectively (e.g.
  • allyl alcohol, 2-buten-4-ol, oleyl alcohol, 2- Hydroxyethyl (meth) acrylate, N-methylolacrylamide and the like) and a reaction product of the carboxyl-containing polymerized compound, and such a binder may contain an unsaturated compound free of isocyanate groups.
  • the equivalent amount of unsaturation of the binder mentioned may generally range from 200 to 3,000, in particular 230 to 1,000, in order to provide film hardness as well as suitable photopolymerization.
  • the acid value may generally be 20 to 300, in particular 40 to 200, to provide sufficient alkali developability after film exposure.
  • the average molecular weight of the binder used is preferably 1,500 to 200,000, in particular 10,000 to 50,000 g / mol.
  • the dispersant is not particularly limited, but cationic, anionic, amphoteric, zwitterionic or neutral nonionic dispersants are well known.
  • Preferred examples of the anionic dispersant include alkylbenzene-sulfonate, alkylnaphthalene-sulfonate, alkylsulfosuccinate, or naphthalene formaldehyde sulfonate, and preferred examples of cationic dispersant include benzyltributylammonium chloride salt and the like.
  • the amphoteric or nonionic dispersant may preferably include polyoxyethylene, alkyl or amidopropyl, and the like.
  • organic solvents binders, dispersants and the like can be added in a content range known in the art as a pigment composition for color filters.
  • the invention also provides a photoresist having the following configuration:
  • the organic solvent, the binder, the optional dispersant, and the like may be the above-described organic solvent, binder, dispersant, or the like.
  • the photocurable monomer contains one or more reactive double bonds and additional reactive groups in the molecule.
  • Useful photocurable monomers in this connection are in particular reactive solvents or reactive diluents, for example mono-, di-, tri- and polyfunctional acrylates and methacrylates, vinyl ethers, glycidyl ethers and the like. Additional reactive groups include allyl, hydroxyl, phosphate, urethanes, secondary amines, N-alkoxymethyl groups and the like.
  • Monomers of this kind are known in the art and are described, for example, in Roempp, Lexikon, Lacke und Druckmaschine, Dr. Ulrich Zorll, Thieme Verlag Stuttgart-New York, 1998, p. 491/492. The document is incorporated herein by reference.
  • the choice of monomer depends in particular on the type and intensity of irradiation used, the desired reaction by the photoinitiator and the film properties.
  • These photocurable monomers can also be used individually or in combination of monomers.
  • the photoinitiator is a compound which forms a reaction intermediate capable of inducing a polymerization reaction of the monomer and / or binder, for example, as a result of absorption of visible or ultraviolet light.
  • Photoinitiators are also known in the art and are described, for example, in Roempp Lexikon, Lacke und Druckmaschine, Dr. Ulrich Zorll, Thieme Verlag Stuttgart-New York, 1998, p. 445/446. The document is incorporated herein by reference.
  • the optionally added additive may be used without limitation as long as it meets each purpose.
  • fatty acids fatty amines, alcohols, bean oils, waxes, rosin, resins, benzotriazole derivatives and the like can be used. More preferably, stearic acid or behenic acid may be used as the fatty acid, and stearilamine may be used as a fatty amine.
  • the content ratio of each component in the photoresist may be applied as it is known in the art.
  • the technique for producing the colored pixel pattern based on the pigment or solid pigment preparation used in the present invention is not particularly limited.
  • other methods such as offset printing, chemical grinding or inkjet printing are also suitable.
  • Selection of suitable binders and solvents or pigment transfer media, and also other additives, should depend on the method specified.
  • Inkjet methods including thermal inkjet printing as well as mechanical and pressure mechanical inkjet printing, utilize pure organic vehicle media as well as aqueous organic vehicle media for pigments and optionally binders, with aqueous organic vehicle media being substantially preferred.
  • the present invention also provides a method of manufacturing a color filter, which is subjected to the following steps:
  • step (b) treating the milled product obtained in step (a) in the presence of a photocurable monomer, a photoreaction initiator, a binder and a solvent to form a photoresist;
  • the substrate of step (c) is a glass substrate.
  • the present invention provides a color filter comprising the pigment composition, and also provides a display comprising at least one color filter.
  • Copper phthalocyanine crude was added to 98% sulfuric acid, and then stirred at 40 ° C. for 2 hours, then precipitated by precipitation in water, washed with water to dryness, dried and pulverized to obtain alpha-type copper phthalocyanine.
  • Kneading was carried out at 90 ° C. for 15 hours after adding 92 parts by weight of Heliogen @ Blue D6700T (epsilon copper phthalocyanine, BASF), 8 parts by weight of phthalimidomethyl copper phthalocyanine, 100 parts by weight of diethylene glycol, and 700 parts by weight of ground salt. After that, the kneaded material was stirred in an aqueous 1% HCl solution at 70 ° C. for 2 hours, and then washed with water, dried and dried to obtain a pigment.
  • Heliogen @ Blue D6700T epsilon copper phthalocyanine, BASF
  • phthalimidomethyl copper phthalocyanine 100 parts by weight of diethylene glycol
  • ground salt 700 parts by weight
  • alpha copper phthalocyanine comprising 8 parts by weight of phthalimidomethyl copper phthalocyanine, 18.4 parts by weight of D6700T (BASF), 1.6 parts by weight of phthalimidomethyl copper phthalocyanine, 100 parts by weight of diethylene glycol, and 500 parts by weight of ground salt
  • 5 parts by weight of lauryl ammonium monosulfo copper phthalocyanine was added and kneading at 70 ° C. for 2 hours.
  • the pigment was obtained by washing with water, drying and drying.
  • alpha phthalocyanine pigment 20 parts by weight of alpha phthalocyanine pigment, 1.3 parts by weight of nitrophthalimidomethyl copper phthalocyanine, 30 parts by weight of polyethylene glycol, and 150 parts by weight of salt were added to the kneader and milled at 100 ° C. for 20 hours, which was then 1500 parts by weight of 0.1% hydrochloric acid.
  • the aqueous solution was heated to 80 ° C. and stirred for 3 hours, and then washed with water, dried and dried to obtain a pigment.
  • x is a color point, and when y is 0.085, the larger the value, the deeper the color. Therefore, a pigment having a relatively large value may use fewer pigments to express the same color, so that the thickness of the coating film is thin, thereby improving the brightness.
  • the blue pigment is recognized in the art as a difference that the x value difference can also have a critical significance of 0.001.
  • the Y represents the brightness, and the larger the value, the better the brightness, and the greater the CR, the better the contrast ratio.
  • the viscosity is a data indicating the storage stability, the less the initial value and the numerical change after 1 week at 45 °C shows the excellent storage stability.
  • the pigment compositions of Examples 1 to 5 according to the present invention exhibit superior optical and viscosity properties than the comparative examples and commercially available products.
  • the pigment composition according to the present invention not only has improved color characteristics, but also obtains excellent characteristics of stability and dispersibility, and thus can be used for color filters for displays and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des compositions pigmentaires pour filtres colorés, et des compositions pigmentaires contenant des composés comme ceux de la formule (1) tels que définis dans la description. De telles compositions pigmentaires permettent d'obtenir des caractéristiques colorées, et présentent une excellente stabilité et une excellente dispersion.
PCT/KR2010/008786 2009-12-24 2010-12-09 Dérivés pigmentaires contenant du pyrazole destinés à afficher des filtres colorés Ceased WO2011078502A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2009-0130564 2009-12-24
KR1020090130564A KR101130651B1 (ko) 2009-12-24 2009-12-24 디스플레이의 컬러 필터용 피라졸 함유 안료 유도체

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WO2011078502A2 true WO2011078502A2 (fr) 2011-06-30
WO2011078502A3 WO2011078502A3 (fr) 2011-11-17

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210261801A1 (en) * 2018-07-18 2021-08-26 Dic Corporation Copper phthalocyanine pigment composition and ink composition containing same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101627352B1 (ko) * 2014-04-02 2016-06-07 한국교통대학교산학협력단 신규한 안료 첨가제, 이의 제조방법 및 이를 포함하는 안료 분산 조성물

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Publication number Priority date Publication date Assignee Title
DE3838814A1 (de) * 1987-12-22 1989-07-06 Hoechst Ag Neue pigmente und ihre verwendung
ES2071280T3 (es) * 1990-11-08 1995-06-16 Ciba Geigy Ag Derivados de pigmento conteniendo pirazol.
EP0790281B1 (fr) 1996-02-13 2001-12-05 Ciba SC Holding AG Compositions pigmentaires
WO2005014727A1 (fr) 2003-07-17 2005-02-17 Ciba Specialty Chemicals Holding Inc. Compositions a base de pigment noir

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210261801A1 (en) * 2018-07-18 2021-08-26 Dic Corporation Copper phthalocyanine pigment composition and ink composition containing same
US11987714B2 (en) * 2018-07-18 2024-05-21 Dic Corporation Copper phthalocyanine pigment composition and ink composition containing same

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WO2011078502A3 (fr) 2011-11-17
KR101130651B1 (ko) 2012-04-02
KR20110073817A (ko) 2011-06-30

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