EP1877496A2 - Grüne pigmentzubereitungen auf basis von c.i. pigment green 36 - Google Patents

Grüne pigmentzubereitungen auf basis von c.i. pigment green 36

Info

Publication number
EP1877496A2
EP1877496A2 EP06754811A EP06754811A EP1877496A2 EP 1877496 A2 EP1877496 A2 EP 1877496A2 EP 06754811 A EP06754811 A EP 06754811A EP 06754811 A EP06754811 A EP 06754811A EP 1877496 A2 EP1877496 A2 EP 1877496A2
Authority
EP
European Patent Office
Prior art keywords
pigment
green
salt
component
pigment preparations
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.)
Withdrawn
Application number
EP06754811A
Other languages
German (de)
English (en)
French (fr)
Inventor
Joachim Jesse
Oliver Seeger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1877496A2 publication Critical patent/EP1877496A2/de
Withdrawn legal-status Critical Current

Links

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
    • C09B67/006—Preparation of organic pigments
    • 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092—Dyes in solid form
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters

Definitions

  • the present invention relates to green pigment preparations which are essential constituents
  • the invention relates to the preparation of these pigment preparations and their use for producing the green component of color filters.
  • the red, green and blue pigment preparations for color filters are usually prepared by mixing the pigments required to form the respective desired hue in the pigment formation or in the pigment dispersion during the paste production.
  • the pigment pastes are then converted into radiation-curable inks by the addition of binders, free-radically polymerizable monomers, photoinitiators, solvents and other conventional auxiliaries, which are applied by appropriate printing processes such as offset printing directly in the desired raster form on the glass plates used, for example, in LCD elements or are first applied in the form of thin films on the glass plates, which then eg be transferred by photolithographic embossing in the desired red / green / blue grid.
  • the green pigment preparations used here are usually based on green and yellow or blue pigments. For optimal use in color filters pigment preparations with high transparency, high chroma (hue purity) and high color strength are needed.
  • Pigment dispersions for color filters are prepared in US Pat. No. 5,821,016 by using the respective pigments, for example a mixture of Cl. Pigment Green 36 and Cl. Pigment Yellow 83 or Cl. Pigment Yellow 139, in the presence of at least equal to double amounts of a dispersing resin based on styrene / maleic acid, large amounts of an organic solvent based on glycol ether or lactone and sometimes small amounts of an additional dispersant are ground in a bead mill. The millbase obtained is then transferred directly into a resist ink.
  • dispersing aids in the description are mentioned as dispersing aids in the description.
  • EP-A-902 327 there is no separate production of a pigment paste, but instead the radiation-sensitive dispersion is prepared directly by mixing all the components (pigments, binders, monomers, photoinitiator, solvent).
  • the pigments are first kneaded together with a special dispersing graft copolymer, optionally an additional binder resin and solvent. After further addition of the solvent, the kneaded material is then subjected to ball-milling or sand-grinding with glass beads, it also being possible to add dispersing aids.
  • dispersing aids anionic polymeric dispersants, surface active agents and also phthalocyanine derivatives are mentioned as dispersing aids, but these are not used in the examples.
  • red, green and blue pigment mixtures mentioned, with special reference being made to yellow pigments based on insoindoline.
  • J P-A-2001-042117 describes green pigment dispersions for color filter application prepared by dispersing Cl.
  • Pigment Green 36 and Cl previously subjected to salt kneading in the presence of maleic acid-modified rosin and polyethylene glycol.
  • Pigment Yellow 138 can be obtained in ⁇ -butyrolactone. It is mentioned only in the specification that the surface of the yellow pigment may have been subjected to a treatment with a rosin resin, an acidic or basic modification or a treatment with a pigment derivative.
  • WO-A-03/035770 describes green pigment preparations which are obtained by joint salt kneading of a dry salt-milled yellow pigment, for example Cl. Pigment Yellow 139 or 150, and a green pigment, eg Cl. Pigment Green 36, which may have previously also been subjected to dry salt grinding, can be prepared in the presence of diacetone alcohol.
  • the salt-free washed and dried pigment mixture is then converted into a dispersion in propylene glycol monomethyl ether in the presence of a pigment derivative or a polymeric surfactant with a dispermat, to which the binder polymer is then added.
  • the known green pigment preparations can not satisfy the requirement profile for color filters satisfactorily. In particular, their transparency is usually insufficient.
  • the invention therefore an object of the invention to provide green pigment preparations having high chroma, high color strength and high transparency.
  • the pigment preparations of the invention are based on Cl. Pigment Green 36 alone or on mixtures of Cl. Pigment Green 36 with further green, yellow and / or blue pigments as component (A).
  • pigments additionally suitable as component (A) are Cl. Pigment Green 7, Cl. Pigment Yellow 83, 93, 94, 95, 109, 110, 128, 138, 139, 150, 166 and 185 and Cl. Pigment Blue 15: 3 and 15: 4 called.
  • Particularly suitable are mixtures of Cl. Pigment Green 36 with yellow pigments, especially with Cl. Pigment Yellow 138, 139, 150 and 185, where C I. Pigment Yellow 138 and 150 are very particularly suitable mixture components.
  • the pigments (A) can be used in the form of the crude pigments obtained in the synthesis or as already formed (finished) pigments.
  • So Cl. pigment Green 36 is used, for example, as a crude pigment obtained in a synthesis carried out analogously to DE-A-24 15 249, or as a shaped pigment which has been subjected to a solvent finish in nitrophenol described in DE-A-1242 180.
  • the pigment preparations according to the invention preferably contain a pigment derivative of the formula I.
  • X is -SO 3 H, -SO 3 " M + , -SO 3 - N + R 1 R 2 R 3 R 4 , -SO 2 NR 1 R 2 , -CH 2 NR 1 R 2 , -CH 2 R 5 ,
  • R 1 , R 2 , R 3 and R 4 are independently hydrogen; C r C 22 alkyl or C 2 -C 22 alkenyl, whose carbon chain may be interrupted in each case by one or more groups -O-, -S-, -NR 6 -, -CO- or -SO 2 - and / or which may be mono- or polysubstituted by hydroxyl, halogen, aryl, C 1 -C 4 -alkoxy and / or acetyl; C 3 -C 8 -cycloalkyl, whose carbon skeleton may be interrupted by one or more groups -O-, -S-, -NR 6 - or -CO- and / or which is mono- or polysubstituted by hydroxyl, halogen, aryl, C r C 4 alkoxy and / or acetyl may be substituted; Dehydroabietyl or aryl; R 1 and R 2 or R 1 , R 2 and
  • R 5 is a remainder
  • R 6 is hydrogen or C r C 4 alkyl
  • a arylene which may be substituted by halogen, arylsulfonyl or -COR 7 or -CO-C 6 H 4 -CO-;
  • R 7 is C r C 4 alkyl or phenyl; n is an integer or fractional number from 1 to 4.
  • the metal salts of the pigment derivatives (B) are preferably the alkali metal salts, and more preferably the alkaline earth metal salts.
  • the pigment preparations of the invention particularly preferably contain as component (B) a pigment sulfonic acid or its alkaline earth or ammonium salt.
  • Examples of particularly suitable components (B) are sulfonic acid derivatives of copper phthalocyanine pigments and salts thereof. Preferably, these derivatives contain 1, 2 to 1, 9 sulfo groups per molecule.
  • Examples of very particularly suitable components (B) are sulfonic acid derivatives of quinophthalone pigments and their alkaline earth metal salts, e.g. the magnesium and / or calcium salts, and ammonium salts, e.g. the distearyldimethyl, distearylmethyl, stearyldimethyl, distearyl, stearyl, lauryl and dehydroabietylammonium salts.
  • alkaline earth metal salts e.g. the magnesium and / or calcium salts
  • ammonium salts e.g. the distearyldimethyl, distearylmethyl, stearyldimethyl, distearyl, stearyl, lauryl and dehydroabietylammonium salts.
  • component (B) Since the green component in color filters should as a rule have a yellowish-tinted green, yellow pigment derivatives are preferred as component (B).
  • Quinophthalone derivatives which are particularly suitable as component (B) are derived from Cl. Pigment Yellow 138 and have the following formula Ia:
  • the pigment preparations according to the invention may also contain mixtures of different pigment derivatives as component (B).
  • the pigment preparations according to the invention contain from 1 to 20% by weight, preferably from 4 to 12% by weight, of component (B), based on component (A).
  • the pigment preparations according to the invention may contain, as further component (C), a surface-active agent other than (B).
  • the pigment preparations containing only components (A) and (B) already have the desired advantageous properties of use, so that an addition of component (C) can be omitted.
  • a component (C) is used, its amount used is generally from 0.1 to 99% by weight, in particular from 2 to 30% by weight, based on the components (A) and (B).
  • component (C) it is possible to use anionic, nonionic, cationic or amphoteric polymeric surface-active agents, anionic and nonionic surface-active agents being preferred.
  • Suitable nonionic surfactants are especially based on polyethers, i. the alkoxylation, especially ethoxylation and / or propoxylation l michs located near the alkoxylation.
  • Suitable anionic surfactants are, for example, the acidic phosphoric, phosphonic, sulfuric and / or sulfonic acid esters of polyethers.
  • anionic surface-active agents are polymers based on ethylenically unsaturated carboxylic acids, in particular the homopolymers and copolymers of ethylenically unsaturated mono- and / or dicarboxylic acids, such as (meth) acrylic acid and maleic acid, which contain non-acid-containing vinyl monomers, such as styrene, in copolymerized form can, the alkoxylation of these homo- and copolymers and the salts of these polymers.
  • ethylenically unsaturated carboxylic acids in particular the homopolymers and copolymers of ethylenically unsaturated mono- and / or dicarboxylic acids, such as (meth) acrylic acid and maleic acid, which contain non-acid-containing vinyl monomers, such as styrene, in copolymerized form can, the alkoxylation of these homo- and copolymers and the salts of these polymers.
  • anionic polyurethane-based surfactants are also suitable as component (C).
  • natural resins e.g. Rosin
  • modified natural resins e.g. modified rosin resins
  • C surface-active agent
  • mixtures of surfactants (C) can be used.
  • the pigment preparations according to the invention are advantageously obtainable by the likewise inventive preparation process, in which the pigment (A) is subjected to salt kneading or salt grinding in the presence of the pigment derivative (B).
  • Surfactants (C) can, if desired, be added to the pigment preparations according to the invention before, during or after the salt-grinding or salt-kneading. If the pigment preparations according to the invention contain water-soluble surface-active agents, they are expediently added or supplemented after the aqueous desalting of the kneaded or ground pigment preparation and re-suspension in water. The aqueous preparation is then freeze-dried or spray-dried.
  • crystalline inorganic salts are used as grinding salt.
  • the salts or salt mixtures customary for salt kneading and salt grinding can be used. Preference is given to sodium chloride and sodium sulfate.
  • the weight ratio of salt to the mixture of (A) and (B) can be up to 12: 1 and is preferably from 3: 1 to 9: 1.
  • the salt kneading preferred according to the invention is carried out in the presence of an organic solvent.
  • Suitable organic solvents are in particular water-miscible organic solvents, in particular higher-boiling solvents based on monomeric, oligomeric and polymeric C 2 -C 3 -alkylene glycols and their C 1 -C 4 -
  • Alkyl ethers examples include: propylene glycol monomethyl and monoethyl ethers, diethylene glycol, diethylene glycol monomethyl and monoethyl ether, triethylene glycol, triethylene glycol monomethyl and monoethyl ether, dipropylene glycol, dipropylene glycol monomethyl and monoethyl ether and liquid polyethylene and polypropylene glycols.
  • the salt kneading the invention can be carried out under cooling or heating at temperatures of below 0 0 C to 18O 0 C.
  • Preferred Knettemperaturen are 80 to 140 0 C.
  • the kneading time is usually 1 to 24 hours, especially 2 to 5 hours.
  • kneading unit Particularly suitable as a kneading unit are single-shaft and double-shaft kneaders and rollers.
  • the workup of the kneading material obtained can be carried out as usual by stirring in water, filtering, washing with water and drying.
  • the dried product is subjected to deagglomeration milling, e.g. subjected in rotor or jet mills.
  • the aqueous filter cake can also be freeze-dried or spray-dried.
  • the salt grinding according to the invention is preferably carried out in the absence of an organic solvent. In individual cases, however, it may be advantageous to add an organic solvent in amounts of about 0.1 to 10 wt .-%, based on the components (A) and (B).
  • suitable solvents which may be mentioned are xylene, ethylene glycol and dialkyl phthalates, e.g. Phthalic acid methyl ester.
  • the salt grinding can be carried out in continuous or discontinuous ball mills, vibratory mills or attritors using the usual grinding balls and / or optionally beaters.
  • the grinding temperatures are generally from room temperature to 130 0 C, preferably at 40 to 11O 0 C.
  • the grinding times are to be matched to the grinding unit used.
  • the grinding according to the invention can be carried out in air, but is preferably carried out under inert gas.
  • the millbase obtained can be worked up as described in salt kneading.
  • the pigment preparations according to the invention are distinguished by high chroma and high color strength and high flocculation stability in the pastes and paints used for the production of color filters and show high transparency in an applied form, e.g. as a film or as a print image.
  • Pigment (A1) Cl. Pigment Green 36 having a bromine content of 59.0 wt .-% and a chlorine content of 5.3 wt .-%, prepared analogously to Example 2 of DE-A-24 15 249th
  • Pigment derivative (B1) monosulfonic acid from Cl. Pigment Yellow 138 of the above-defined formula Ia, prepared according to Example 1 of WO-A-02/00643
  • Pigment derivative (B2) copper phthalocyanine sulfonic acid having 1.5 sulfo groups per molecule
  • a mixture of 1050 g of pigment (A1), 52.2 g of pigment derivative (B1), 5800 g of sodium sulfate and 950 g of triethylene glycol was stirred for 2 h at 130 ° C. in a 10 l high-speed kneader (Turbulent high-speed kneader TR 10 from Drais). Temperature of the plasticine) kneaded.
  • a mixture of 1000 g of pigment (A1), 5500 g of sodium sulfate and 1200 g of triethylene glycol was kneaded and worked up analogously to Example 1.
  • a mixture of 40 g of pigment (A1), 2 g of pigment derivative (B1), a solution of 4 g of a polymeric surface active agent (Solsperse ® 32000; Fa Lubrizol / Noveon.) was dissolved in 37 g of triethylene glycol and 220 g of sodium sulfate in the kneader from Example 2 Kneaded at 130 0 C for 2 h and worked up analogously to Example 1.
  • a mixture of 8.4 g of pigment (A1) and 0.42 g of pigment derivative (B1) was added to 67.2 g of sodium chloride for 24 h in a 600 ml heatable vibratory mill filled with 1500 g of 25 mm diameter steel balls 100 0 C ground.
  • the millbase obtained was introduced into 2 l of water.
  • the suspension was mixed with 2 ml of 20% strength by weight hydrochloric acid and stirred at 7O 0 C for 2 h.
  • the pigment preparation was filtered off, washed salt-free with water, dried at 70 0 C in a convection oven and ground.
  • the pigment pastes obtained after separation of the zirconia spheres were applied to an acetate film using a wire-wound rod as a 12 ⁇ m thick film and flashed off at room temperature for 12 hours.
  • the squeegees were laid over black and white cardboard.
  • the visual assessment was on a scale of 5 (significant difference, i.e. substantially more transparent) to 0 (no difference, same transparency), with the doctor blades made with the pigment preparations of Comparative Examples serving as the standard.
  • the doctoring was measured with a Cary 5E photo-spectrometer (Varian) using the measuring geometry of an open integrating sphere.
  • the proportion of forward scatter i. the proportion of light which is broken away from the solder when a sample is irradiated is a measure of the fineness of the color pigment and its distribution in the doctor blade.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
EP06754811A 2005-04-25 2006-04-24 Grüne pigmentzubereitungen auf basis von c.i. pigment green 36 Withdrawn EP1877496A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005019400A DE102005019400A1 (de) 2005-04-25 2005-04-25 Grüne Pigmentzubereitungen auf Basis von C.I. Pigment Green 36
PCT/EP2006/061784 WO2006114403A2 (de) 2005-04-25 2006-04-24 Grüne pigmentzubereitungen auf basis von c.i. pigment green 36

Publications (1)

Publication Number Publication Date
EP1877496A2 true EP1877496A2 (de) 2008-01-16

Family

ID=37037451

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06754811A Withdrawn EP1877496A2 (de) 2005-04-25 2006-04-24 Grüne pigmentzubereitungen auf basis von c.i. pigment green 36

Country Status (8)

Country Link
US (1) US20090121201A1 (zh)
EP (1) EP1877496A2 (zh)
JP (1) JP2008538792A (zh)
KR (1) KR20070122229A (zh)
CN (1) CN101163753A (zh)
DE (1) DE102005019400A1 (zh)
TW (1) TW200643115A (zh)
WO (1) WO2006114403A2 (zh)

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CN101679765A (zh) * 2007-04-13 2010-03-24 巴斯夫欧洲公司 制备细粒颜料的方法
US20100043672A1 (en) * 2007-04-13 2010-02-25 Basf Se Method of finishing organic pigments
US8551237B2 (en) 2007-12-10 2013-10-08 Basf Se Synthesis of colorants in mixing apparatus
JP5266900B2 (ja) * 2008-06-19 2013-08-21 東レ株式会社 カラーフィルター用緑色着色剤組成物、およびカラーフィルター
CN102766350A (zh) * 2011-05-04 2012-11-07 丽王化工(南通)有限公司 一种液晶光阻用的黄色颜料衍生物制备方法
JP2013064993A (ja) * 2011-08-31 2013-04-11 Fujifilm Corp カラーフィルタの製造方法、カラーフィルタ、及び固体撮像素子
TW201348346A (zh) * 2012-03-07 2013-12-01 Fujifilm Corp 著色組成物、彩色濾光片、液晶顯示裝置、有機ｅｌ顯示裝置及固體攝影元件
CN105111784B (zh) * 2015-09-28 2017-11-24 温州金源新材料科技有限公司 高性能颜料蓝60的制备方法
JP6638299B2 (ja) * 2015-10-07 2020-01-29 コニカミノルタ株式会社 光硬化型インクジェットインク及び画像形成方法
TWI761260B (zh) * 2016-09-02 2022-04-11 日商住友化學股份有限公司 著色組成物及化合物

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Also Published As

Publication number Publication date
JP2008538792A (ja) 2008-11-06
WO2006114403A3 (de) 2007-01-11
TW200643115A (en) 2006-12-16
KR20070122229A (ko) 2007-12-28
WO2006114403A2 (de) 2006-11-02
US20090121201A1 (en) 2009-05-14
CN101163753A (zh) 2008-04-16
DE102005019400A1 (de) 2006-11-02

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