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WO2012084824A1 - Procédé de préparation d'un produit à base de particules de phtalocyanine de cuivre (cupc) - Google Patents

Procédé de préparation d'un produit à base de particules de phtalocyanine de cuivre (cupc) Download PDF

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Publication number
WO2012084824A1
WO2012084824A1 PCT/EP2011/073238 EP2011073238W WO2012084824A1 WO 2012084824 A1 WO2012084824 A1 WO 2012084824A1 EP 2011073238 W EP2011073238 W EP 2011073238W WO 2012084824 A1 WO2012084824 A1 WO 2012084824A1
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WO
WIPO (PCT)
Prior art keywords
cupc
particles
polar solvent
copper phthalocyanine
process according
Prior art date
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Ceased
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PCT/EP2011/073238
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English (en)
Inventor
Jai Won Park
Hyunsu Lee
Kisuck Jung
Eunha Jeong
Sangmin Han
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Solvay SA
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Solvay SA
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Priority to KR1020137008658A priority Critical patent/KR20130086216A/ko
Priority to KR1020127017204A priority patent/KR101343758B1/ko
Priority to JP2013545266A priority patent/JP2014503647A/ja
Priority to CN2011800681479A priority patent/CN103403101A/zh
Publication of WO2012084824A1 publication Critical patent/WO2012084824A1/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
    • 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
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • 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
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • 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
    • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
    • C09B67/0019—Influencing the physical properties by treatment with an acid, H2SO4 of phthalocyanines
    • 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
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • 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
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0086—Non common dispersing agents anionic dispersing agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices

Definitions

  • the present invention generally relates to copper phthalocyanine (CuPc) and processes of preparing the same. More particularly, the present invention relates to a new efficient and economical process for preparing CuPc pigments with better dispersibility, said CuPc pigments being especially suitable for the preparation of color filters used for displaying colour images, to the CuPc pigments prepared thereby, as well as to liquid crystal display devices in which the foregoing pigments are incorporated.
  • CuPc copper phthalocyanine
  • Copper phthalocyanine blue (C.I. Pigment Blue 15) is without exception the most significant of any synthetic organic pigment produced today due to its excellent color strength and durability. It has a high molar absorption
  • Copper phthalocyanine has many crystal forms.
  • those known to have actual applications include alpha, beta and epsilon crystal forms of copper phthalocyanine. It is a common practice to use the beta crystal form to impart a greenish blue colour, while using the alpha crystal form to impart a reddish blue colour. Further, the epsilon crystal form is employed when a blue colour, which is more reddish than that produced using the alpha crystal form, is required.
  • Copper phthalocyanine is commercially available in three crystal forms, namely, alpha, beta and epsilon.
  • the alpha crystal which uses the Colour Index nomenclature, is described as Pigment Blue 15, 15: 1 and 15:2, and is a clean, bright red shade blue.
  • the beta crystal which is described as Pigment Blue 15:3 and 15:4, is a clean green shade blue, and the important epsilon form is the most reddish shade of blue. Its halogenated derivatives are also used as important green pigments.
  • the commercially available "crude" copper phthalocyanine particles include various crystal forms, most of which exhibit beta- crystallographic form.
  • the beta crystal form copper phthalocyanine is commercially available from various companies such as Toyo Ink (Japan), Dainippon Ink & Chemicals Co. (Japan), etc.
  • the beta crystal form copper phthalocyanine is subjected to crystal phase conversion into alpha crystal form by acid pasting, which is described, for instance, in Ullmann's Encyclopedia of Industrial Chemistry, Fifth Completely Revised Edition, 1992, Volume A20, pp. 225-226, incorporated herein by reference.
  • Copper phthalocyanine (CuPc) particles exhibiting an ⁇ crystallographic form are typically prepared from CuPc particles with at least 50 wt % of the particles exhibiting an a crystallographic form as a starting material.
  • a typical process of producing epsilon crystal form copper phthalocyanine is the solvent salt milling process, wherein copper phthalocyanine particles exhibiting alpha crystal form and copper
  • phthalocyanine particles exhibiting epsilon crystal form are milled in an organic solvent.
  • WO 2009/037233 discloses a process wherein CuPc particles exhibiting alpha-crystallographic form are subjected to heating in a solvent, optionally with milling beads, for crystallographic conversion to epsilon type. The heating is then followed by a kneading process for micronizing the epsilon type CuPc particles.
  • the alpha-type CuPc particles are kneaded under different temperature conditions. During the kneading step, two CuPc derivatives are sequentially added.
  • the products obtained by the above processes are produced in the form of agglomerates, which do not display the desired performance properties.
  • EP1580239A1 also discloses a process for the production of an epsilon-crystal form copper phthalocyanine comprising heating a copper phthalocyanine in an organic solvent, such as t-amylbenzene, sulfolane, etc., in the presence of a Lewis acid.
  • WO 08/083799A discloses a pigment composition of copper
  • phthalocyanine exhibiting epsilon crystallographic form, which is produced with application of a wet grinding process, more particularly a salt kneading operation.
  • US 4239685A discloses a process for preparation of phthalocyanine pigments from a phthalocyanine press paste obtained by hydrolysis of a sulphuric solution of phthalocyanine, in which a small quantity of a water- insoluble crystallizing solvent, in the presence or absence of a non-crystallizing solvent, is incorporated with stirring in said press paste, and then the solvent or solvents is or are eliminated and the paste is dried, and the pigments thus obtained are collected.
  • US 3801591 A discloses a production of metal phthalocyanine pigment composed almost exclusively of the ⁇ I polymorph in which crude metal phthalocyanine is subjected to controlled precipitation in two sages followed by conditioning of the resultant slurry under intense agitation to generate an air/liquid interface and thereby facilitate flocculation, hence filtration.
  • GB 1411880A discloses a process for the production of copper
  • ⁇ -modification and/or ⁇ -modification copper phthalocyanine to an a-/ ⁇ -modification mixture by grinding in a ball mill, treating the mixture with a liquid at a temperature at which no or substantially no conversion into the ⁇ -modification takes place (liquid-specific limiting temperature) to effect conversion of a-modification to ⁇ -modification and to form a mixture of the liquid with pure or substantially pure ⁇ -modification and optionally isolating the pure or substantially pure ⁇ -modification of copper phthalocyanine.
  • a liquid at a temperature at which no or substantially no conversion into the ⁇ -modification takes place liquid-specific limiting temperature
  • phthalocyanine particles have problems in that the resulting CuPc particles still lack dispersibility, which results in still to improve color filter pigments, for instance regarding the contrast ratio of the color filters prepared from the copper phthalocyanine particles.
  • the resulting CuPc particles still lack dispersibility, which results in still to improve color filter pigments, for instance regarding the contrast ratio of the color filters prepared from the copper phthalocyanine particles.
  • the purpose of the present invention is to resolve the problems of the conventional preparation process, e.g. relatively low dispersibility resulting in poor contrast ratios from the resultant color filter pigment.
  • the present invention therefore relates to a process for preparing a product based on copper phthalocyanine (CuPc) particles, said process comprising adding, to the CuPc particles, during or after their preparation, at least one non- polar solvent in an amount of less than 10 % by weight of the CuPc particles.
  • CuPc copper phthalocyanine
  • the inventors of the present invention have indeed discovered that the performance of the final color filter pigment for producing blue pigments may be improved when some non-polar solvents were added in an amount of less than 10 % by weight of the copper phthalocyanine particles during or after the preparation of copper phthalocyanine particles exhibiting epsilon form.
  • the present invention is directed to developing a new and more efficient process of preparing copper phthalocyanine-based products, which satisfies the above-mentioned features.
  • Copper phthalocyanine is typically developed for effective use as a blue pigment of color filters for LCDs. Such color filters must be highly transparent, homogeneous and be prepared in a layer with uniform thickness. These features are decided by several factors including chemical purity, crystallographic purity, primary particle size and particle size distribution of copper phthalocyanine particles. In this regard, the disclosure teaches a new and more efficient process of preparing copper phthalocyanine.
  • non-polar solvent selected from alicyclic and aromatic compounds.
  • suitable examples of non-polar solvents are those selected from the group consisting of n-hexane, pentane, cyclopentane, petroleum ether, cyclohexane, benzene, naphthalene, toluene, or cumene, preferably cyclohexane, benzene or naphthalene.
  • the amount of the non-polar solvent is not limited but the non-polar solvent is generally added in an amount of at least 0.1 % by weight of the CuPc particles, particularly at least 0.5 % by weight, more particularly at least 1 % by weight.
  • the non-polar solvent is commonly added in an amount of less than 10 % by weight of the CuPc particles, particularly at most 5 % by weight, more particularly at most 3 % by weight.
  • the amount of non-polar solvent may typically be from 0.1 to less than 10 % by weight of the CuPc particles, preferably from 0.5 to 5 %, more preferably from 1 to 3 % by weight.
  • the at least one non polar solvent may be combined with at least one polar solvent.
  • the at least one polar solvent may be present preferably in an amount of from 3.3 to 20 % by weight of the CuPc particles, more preferably from 5 to 10 % by weight, in particular from 5 to less than 10 % by weight.
  • a surfactant acting as a dispersant may be added in the process of the invention, especially in the same process step as the non-polar solvent.
  • Suitable surfactants include organic carboxylic or sulfonic acids, amines or ammonium compounds, or rosin and its derivatives, for instance lauric acid, capric acid, citric acid, oleic acid, stearic acid, dodecylbenzene sulfonic acid (DBSA), p-toluenesulfonic acid (pTSA), lauryl amine, benzylamine, hexadecylamine, dodecylamine, aniline,
  • 6-aminohexanoic acid 4-(aminomethyl)benzoic acid, cetyltrimethyl ammonium chloride, and combinations thereof, preferably cetyltrimethyl ammonium chloride, rosin and its derivatives, and combinations thereof.
  • rosin is defined herein as a solid form of resin obtained from pines and some other plants, mostly conifers, which chiefly consists of different resin acids, especially abietic acid. Mixtures of this kind that are readily available and occur in nature include, but are not limited to, tall oil rosin, gum rosin or wood rosin.
  • rosin acids of the abietic type and/or the pimaric type such as abietic acid, palustric acid, neoabietic acid, levopimaric acid, pimaric acid, isopimaric acid or dehydroabietic acid, among others, in varying amounts.
  • rosin acids with one carboxylic acid functionality rosin acids with two or more carboxylic acid functionalities are also considered as rosin acids in the meaning of the present invention.
  • the expression "rosin derivatives" is defined as any derivative of the rosin, for example, hydrogenated rosin, dimerized rosin, poly-pale rosin, rosin substituted by ester groups, etc.
  • a surfactant When a surfactant is added, its amount is not limited but is in general from 0.1 to 25 % by weight of the CuPc particles, preferably from 0.5 to 20 % by weight, more preferably from 1 to 15 % by weight.
  • At least one of an akaline or alkaline earth metallic salt may be added during and/or after the kneading step.
  • the alkaline metal of the alkaline metallic salt is typically selected from sodium, potassium and lithium, in particular sodium.
  • the alkaline earth metal of the alkaline earth metallic salt is often selected from calcium and magnesium, most often calcium.
  • the metallic salt is advantageously an alkaline earth metallic salt.
  • alkaline and alkaline earth metallic salts are alkaline and alkaline earth metal chlorides such as NaCl, KC1, LiCl, CaCl 2 , MgCl 2 ; carboxylic acid salts such as CH 3 COONa, (CH 3 COO) 2 Ca ; acidic or basic salts such as NaHC0 3 , NaHS0 4 , Na 2 HP0 4 , Ca(OH)Cl, Ba(OH)Cl, etc. ; especially CaCl 2 and MgCl 2 .
  • alkaline and alkaline earth metal chlorides such as NaCl, KC1, LiCl, CaCl 2 , MgCl 2 ; carboxylic acid salts such as CH 3 COONa, (CH 3 COO) 2 Ca ; acidic or basic salts such as NaHC0 3 , NaHS0 4 , Na 2 HP0 4 , Ca(OH)Cl, Ba(OH)Cl, etc. ; especially CaCl 2 and MgCl 2 .
  • an alkaline or alkaline earth metallic salt When added, its amount is not limited, but it is generally added in an amount from 0.1 to 25 % by weight of the CuPc particles, preferably from 0.5 to 20 % by weight, more preferably from 1 to 15 % by weight.
  • the present invention it has surprisingly been found that by adding non- polar solvent in an amount of less than 10 % by weight, a better dispersibility of the pigment particles can be obtained. It has also been found that the resulting particles exhibit a rounder particle shape. This leads to an improved contrast ratio of the resultant color filter prepared from the pigment particles, as well as to an improved brightness of said color filters.
  • the present invention therefore also relates to copper phthalocyanine (CuPc) particles having a round shape, in particularly to CuPc particles showing an average aspect ratio from 1 : 1 to 2: 1, preferably 1 : 1 to 1.5: 1, more preferably 1.1 to 1.3 : 1 , most preferably around 1 : 1.
  • CuPc copper phthalocyanine
  • the aspect ratio is defined herein as the length of a pigment particle with respect to the width thereof.
  • the aspect ratio is usually determined by an image analysis of pictures taken by transmission electron microscopy (TEM) or scanning electron microscopy (SEM).
  • the mean length (L) can be determined by several methods including measurement of the maximal Feret diameter, the length of the rectangle in which the particle can be inserted or the length L.
  • the mean width of the particles can be determined according to the diameter of a circle of equivalent projection area, the minimal Feret diameter, the width of the rectangle in which the particle can be inserted or the width 1.
  • the aspect ratio (L/l) corresponds to the ratio between a length (L) and the related width (1), especially the maximal Feret diameter on the minimal Feret diameter, the maximal Feret diameter on the diameter of a circle of equivalent projection area, the length of the rectangle in which the particle can be inserted on the width of the rectangle in which the particle can be inserted or the length measured directly on the width measured directly.
  • the aspect ratio of a population of particles is defined as the mean of the aspect ratio of each particle.
  • the aspect ratio is the averaged ratio of the length of particles measured directly on the width of particles measured directly, said lengths and widths being measured on images obtained by TEM.
  • the process of the present invention is especially suitable for preparing CuPc particles exhibiting an ⁇ crystallographic form.
  • the product (CuPc) particles exhibit an ⁇ crystallographic form and the CuPc particles to which the at least one non- polar solvent is added comprise CuPc particles exhibiting an a crystallographic form.
  • the CuPc particles to which the at least one non-polar solvent is added comprise CuPc particles with at least 50 wt % of the particles exhibiting an a crystallographic form.
  • copper phthalocyanine particles exhibiting an ⁇ crystallographic form are added, as seed particles, to the CuPc particles to which the at least one non-polar solvent is added, in an amount of from 10 wt % to 90 wt %, preferably 15 wt % to 50 wt % relative to the total amount of CuPc particles.
  • copper phthalocyanine particles exhibiting an ⁇ crystallographic form may be prepared by heating a starting material comprising at least 50 wt % of CuPc particles exhibiting an a crystallographic form at a temperature higher than or equal to 50°C in the presence of at least one organic liquid and optional milling in the presence of beads.
  • the organic liquid may for instance be selected from the group consisting of N-methyl-2- pyrrolidone, sulfolane, ⁇ , ⁇ -dimethylformamide, glycols such as propylene glycol monomethyl ether acetate, diethylene glycol, alcohols such as diacetone alcohol, acetonitrile, monochlorobenzene, ethylene glycol butyl ether, ketones and quinolines.
  • Milling means a process by which the solids are subjected to attrition, grinding, etc. to achieve particle size reduction.
  • ⁇ CuPc particles may be prepared by kneading a starting material comprising at least 50 wt % of CuPc particles exhibiting an a crystallographic form in the presence of at least one liquid and of at least one inorganic salt.
  • the liquid is generally selected from the group consisting of N-methyl-2-pyrrolidone, sulfolane, N,N-dimethylformamide, diethylene glycol, diacetone alcohol, glycerin, ethylene glycol, propylene glycol, polypropylene glycol, 2-butoxy ethanol, methylene glycol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, dipropylene glycol monomethyl ether, l-methoxy-2-propanol, l-ethoxy-2-propanol, ketones and quinolines.
  • kneading is conducted under temperature conditions such that the temperature profile as a function of time exhibits at least two derivatives of temperature with respect to time (dT/dt) being equal to 0.
  • the two temperatures are associated with the derivatives equal to 0 differing by at least 10°C.
  • kneading is conducted under a constantly or stepwise changing temperature profile.
  • kneading is conducted at the first temperature and then at the second temperature, wherein the first temperature is 80-150°C (preferably 100-120°C) and the second temperature is 30-70°C (preferably 50-60°C).
  • This embodiment provides modification of the temperature during the kneading step by which CuPc particles exhibiting a- crystallographic form is converted to ⁇ crystallographic form and their particle size is significantly reduced.
  • the specific conditions of the kneading or heating step e.g., duration, beads, inorganic salts, etc.
  • the resultant mixture may be stirred for a period of time, and filtered.
  • the filter cake may be washed by reslurrying several times in distilled water, optionally in the presence of an organic solvent.
  • the process of the present invention is also especially suitable for preparing CuPc pigment compositions comprising CuPc particles exhibiting an ⁇ crystallographic form.
  • the non-polar solvent may be added during preparation of a CuPc pigment composition comprising
  • the non-polar solvent may be added in a kneading step, or in a re-slurry step where the filter cake obtained after the kneading step is reslurried in a solvent such as water, a water-miscible solvent or a mixture thereof.
  • a solvent such as water, a water-miscible solvent or a mixture thereof.
  • a non-polar solvent may be added during the kneading step, and subsequently another non-polar solvent may be added during the re-slurry step.
  • the present invention thus also relates to copper phthalocyanine (CuPc) pigment compositions comprising CuPc particles exhibiting an ⁇ crystallographic form obtainable according to the process of the invention. Also, it is related to a color filter comprising copper phthalocyanine particles exhibiting the epsilon crystallographic form obtainable by the process of the present invention.
  • CuPc copper phthalocyanine
  • the present invention also relates to copper phthalocyanine (CuPc) particles exhibiting an ⁇ crystallographic form, obtainable by the process of the invention.
  • CuPc copper phthalocyanine
  • another aspect of the present invention is related to the use, in preparing a product based on CuPc particles, of at least one non-polar solvent in an amount of less than 10 % by weight of the copper
  • Fig. 1 illustrates a TEM image for the copper
  • Example 4 Copper phthalocyanine particles exhibiting epsilon crystallographic form were obtained in an identical manner to that of Example 2, except that 3.0 g of benzene were added during the kneading step.
  • Example 4 Comparative - no addition of non-polar solvent and surfactant
  • Copper phthalocyanine particles exhibiting epsilon crystallographic form were obtained in an identical manner to that of Examples 1 and 2, except that no non-polar solvent, no surfactant and no metallic salts were added. Upon analyzing some dried samples of the resultant copper phthalocyanine particles exhibiting epsilon crystallographic form with the transmission electron microscope (TEM), they were shown to exhibit more agglomeration in the image ( Figure 2).
  • TEM transmission electron microscope
  • the epsilon-CuPc particles obtained according to the process of the present invention in the presence of a non-polar solvent (Example 2), exhibit a higher dispersion level compared to the epsilon-CuPc particles produced according to Example 4, without addition of a non polar solvent.
  • the CuPc particles of the invention have an aspect ratio close to 1 : 1, which is advantageous for higher contrast ratio.
  • Copper phthalocyanine particles exhibiting epsilon crystallographic form were obtained in an identical manner to that of Example 2, except that 0.5 g of rosin and 0.5 g of calcium chloride, or 1.5 g of rosin and 1.5 g of calcium chloride, or 10.0 g of rosin were respectively added during the re-slurry step.
  • Example 8 Conversion of alpha-CuPc to epsilon-CuPc in the presence of cyclohexane and no addition of surfactant
  • Copper phthalocyanine particles exhibiting epsilon crystallographic form were obtained in an identical manner to that of Examples 1 and 2, except that no surfactant and no metallic salts were added. The dried product was then pulverized and the particle shape was better, compared to those of Example 4. Test of the particles in color filters
  • the CuPc pigment in which the non-polar solvent and optionally surfactant were added exhibited improved contrast ratio of the color filter pigment millbase. Such improvement would be derived from better dispersibility and optimized shape of the resultant CuPc particles. Thus, such increased dispersibility and good particle shape has led to the improved contrast ratio of the downstream color filter.
  • Fig. 1 is an image from a Transmission Electron Microscope (TEM) for the copper phthalocyanine particles exhibiting epsilon crystallographic phase prepared by the method according to Example 2.
  • TEM Transmission Electron Microscope
  • Fig. 2 is an image from a TEM for the copper phthalocyanine particles exhibiting epsilon crystallographic phase prepared by the method according to Example 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Optical Filters (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention porte sur un procédé pour la préparation d'un produit à base de particules de phtalocyanine de cuivre (CuPc), ledit procédé comprenant l'ajout, aux particules de CuPc, pendant ou après leur préparation, d'au moins un solvant non polaire à hauteur de moins de 10 % en poids par rapport aux particules de CuPc.
PCT/EP2011/073238 2010-12-22 2011-12-19 Procédé de préparation d'un produit à base de particules de phtalocyanine de cuivre (cupc) Ceased WO2012084824A1 (fr)

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KR101343758B1 (ko) 2013-12-19
KR20130086216A (ko) 2013-07-31

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