WO2010105982A2 - Procédé de préparation de particules de phtalocyanine de cuivre présentant une forme cristallographique alpha - Google Patents

Procédé de préparation de particules de phtalocyanine de cuivre présentant une forme cristallographique alpha Download PDF

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Publication number
WO2010105982A2
WO2010105982A2 PCT/EP2010/053184 EP2010053184W WO2010105982A2 WO 2010105982 A2 WO2010105982 A2 WO 2010105982A2 EP 2010053184 W EP2010053184 W EP 2010053184W WO 2010105982 A2 WO2010105982 A2 WO 2010105982A2
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Prior art keywords
cupc
particles
copper phthalocyanine
acid
substituted
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Ceased
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PCT/EP2010/053184
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English (en)
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WO2010105982A3 (fr
Inventor
Hyunsu Lee
Jai Won Park
Kisuck Jung
Sangmin Han
Dongyoon Kim
Hyunsuk Jeong
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Solvay SA
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Solvay SA
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Priority to JP2012500196A priority Critical patent/JP2012520914A/ja
Priority to CN201080012409.5A priority patent/CN102356130B/zh
Publication of WO2010105982A2 publication Critical patent/WO2010105982A2/fr
Publication of WO2010105982A3 publication Critical patent/WO2010105982A3/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
    • C09B67/0017—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
    • C09B67/0033—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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0035—Mixtures 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/42—Ionic groups, e.g. free acid
    • C09B68/425—Anionic groups
    • C09B68/4253—Sulfonic acid groups
    • 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • C09B68/441—Sulfonic acid derivatives, e.g. sulfonic acid amides or sulfonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents

Definitions

  • the present invention is generally related to copper phthalocyanine (CuPc) and processes of preparing the same. More particularly, the present invention is related to a new efficient and economical process of preparing CuPc pigments with better dispersibility for color filters, which are used for displaying colour images and the CuPc pigments prepared thereby.
  • CuPc copper phthalocyanine
  • a phthalocyanine based organic pigment is excellent in terms of fastness and performance. Thus, it is typically employed as a blue colorant for paints or plastics.
  • copper phthalocyanine is very stable and further desirable since it possesses a variety of fastness.
  • copper phthalocyanine has many crystal forms. Among such 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.
  • 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.
  • pigmentation processes using sulfuric acid which is one of the mineral acids, have been known in the art.
  • an acid pasting process (treating crude copper phthalocyanine when dissolved in a large amount of concentrated sulfuric acid) and an acid slurry process (treating crude copper phthalocyanine with a large amount of sulfuric acid having a concentration insufficient for dissolving the pigment to form a sulfate) are used.
  • the products obtained by the acid pasting or slurry process are generally of poor crystal quality and are produced in the form of agglomerates, which do not display the desired performance properties.
  • the so-called finish is carried out in, for example, solvents while adding surface-active agents.
  • U.S. Patent No. US 3024247 describes a general process of acid-pasting phthalocyanines and blending a phthalocyanine monosulfonic acid with a water slurry of acid-pasted, after chlorinated phthalocyanines to produce non-crystallizing phthalocyanine coloring matters.
  • U.S. Patent No. US 5534055 discloses a process of preparing alpha-phase metal phthalocyanine pigments from crude metal phthalocyanine pigments. Such a process comprises the following steps: (a) acid pasting or acid swelling a crude metal phthalocyanine pigment; (b) dry milling the acid-pasted or acid-swelled metal phthalocyanine pigment; (c) finishing the milled metal phthalocyanine pigment by thoroughly mixing the milled metal phthalocyanine pigment with a finishing solvent mixture; and (d) isolating the alpha-phase metal phthalocyanine pigment. After acid pasting beta CuPc to produce precipitated CuPc, dry milling of precipitated CuPc with stabilizer to produce alpha CuPc is conducted in the presence of sulfonamide derivative of CuPc as a stabilizer.
  • U.S. Patent No. US 6031030 also discloses a process of preparing a paint concentrate, which comprises the following steps: (a) milling or acid pasting a crude metal phthalocyanine to reduce the particles size thereof, thereby forming a modified crude metal phthalocyanine; and (b) kneading a mixture of the modified crude metal phthalocyanine together with a paint vehicle comprising one or more paint solvents to provide a paint concentrate containing the metal phthalocyanine in a pigmentary form dispersed in the paint vehicle. Milling crude CuPc in the presence of a fluidising agent such as a sulfonated CuPc is described to produce alpha CuPc.
  • a fluidising agent such as a sulfonated CuPc
  • the inventors of the present invention discovered that the performance of the final color filter pigment and the entire process time for producing blue pigments may be improved when some additives such as CuPc derivatives were added in the acid- pasting step for the phase conversion from beta to alpha crystallographic type.
  • the purpose of the present invention is to prepare, as an intermediate for producing copper phthalocyanine particles having epsilon form, CuPc particles having alpha crystal form, the particle size of which is very small and the dispersibility of which is better, thereby providing better performance of the color filter produced from the CuPc pigments. Further, it is another purpose of the present invention to provide a process of preparing alpha form copper phthalocyanine having a reduced particle size, which needs a shorter time to obtain the epsilon crystal form copper phthalocyanine with a high crystallographic purity. In this regard, the present invention is directed to developing a new and more efficient process of preparing copper phthalocyanine, which satisfies the above- mentioned features.
  • Acid pasting refers to the dissolution of at least part of the crude CuPc in suitable acids (dissolution step) and precipitation of the dissolved CuPc in suitable media (precipitation step).
  • inorganic acids such as sulfuric acid, chlorosulfonic acid and polyphosphoric acids, especially concentrated sulphuric acid or sulphuric acid monohydrate.
  • the acids are usually used in the form of an aqueous solution. If sulfuric acid is used, then its concentration should be equal to or greater than 90% by weight, preferably equal to or greater than 95% by weight. It is preferable to use concentrated sulfuric acid at about 96% by weight.
  • the amount of aqueous solution to be used in the dissolution step is not limited. However, for economic reasons, the concentration of ground crude copper phthalocyanine may be kept in such a range wherein the resulting mixture may be stirred or ground and incorporated.
  • the amount of aqueous solution used is 2 to 20 times, preferably 5 to 15 times, by weight based on crude pigment.
  • the temperature of the dissolution step is usually from 0 to 100°C, preferably from 5 to 60°C, more preferably from 10 to 40°C, for example room temperature.
  • the duration of the dissolution step is in general of from 30 minutes to 5 hours, in particular from 1 to 3 hours, duration of around 2 hours being suitable.
  • the precipitation medium employed may comprise water, organic solvents or mixtures thereof, preferably water, especially distilled water.
  • the ratio of precipitated medium to the mixture acid / CuPc resulting from the dissolution step is generally from 1 to 50, preferably from 5 to 20, for example around 10.
  • the temperature of the precipitation step may be from 0 to 100°C, in particular from 5 to 60°C, more particularly from 10 to 50°C, working at room temperature being also suitable.
  • the mixture acid / CuPc resulting from the dissolution step is usually added to the precipitation medium at a rate of 1 to 100 g of mixture acid / CuPc per kg of the precipitation medium in 1 minute to 1 hour, preferably at a rate of 1 to 100 g (mixture acid / CuPc) / kg (precipitation medium) in 5 to 30 minutes, for example about 10 g (mixture acid CuPc) / kg (precipitation medium) in about 10 minutes.
  • the precipitation may take place under turbulent flow conditions.
  • the mixture resulting from the dissolution step is then filtered, washed with water and dried.
  • the washing is conducted with distilled water, more preferably with distilled water having a pH of at least 6.
  • Any filtering or drying method known in the art may be used for the filtering and the drying steps.
  • filtering may be done using a gravity system and drying may be conducted in an oven at a temperature of, for example, 120 0 C.
  • CuPc copper phthalocyanine
  • the average number of functional groups per CuPc molecule is 0.5 to 2, preferably about 1.
  • the crude CuPc is preferably completely dissolved in the acid.
  • the weight ratio of the copper phthalocyanine substituted by at least one functional group to the crude copper phthalocyanine is generally higher than or equal to 0.01 , preferably higher than or equal to 0.03, and more preferably higher than or equal to 0.05. Such a proportion is generally lower than or equal to 0.3, preferably lower than or equal to 0.2, more preferably lower than or equal to 0.15.
  • the particles of copper phthalocyanine may be substituted by at least one functional group selected from -SO3H, -
  • Ri is hydrogen, alkyl, alkenyl, aryl or cycloalkyl.
  • the functional group is -
  • the CuPc particles substituted by a functional group is a mixture of at least two different substituted CuPc, for instance a mixture of CuPc particles substituted by -SO3H and CuPc particles substituted by
  • copper phthalocyanine particles exhibiting a ⁇ crystallographic form to be used as a blue pigment is prepared by heating the copper phthalocyanine particles exhibiting an alpha crystallographic form prepared according to the first embodiment at a temperature higher than or equal to 50°C in the presence of an organic liquid and optionally milling in the presence of beads.
  • Milling means a process by which the solids are subjected to attrition, grinding, etc. to achieve particle size reduction.
  • Dry milling means a process by which the solids are subjected to attrition, grinding etc. to achieve particle size reduction while being substantially free of liquid. However, a low level of solvent may be added.
  • the crystal phase conversion and size reduction can take place simultaneously.
  • kneading is conducted in the presence of at least one liquid and at least one inorganic salt.
  • kneading is conducted under certain 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 changing temperature profile or at least one time (stepwise).
  • the process of the present invention can lead to alpha crystal form copper phthalocyanine having a smaller averaged primary particle size of not more than 140 nm, preferably not more than 100 nm. Further, a better dispersibility of the pigment particles can be obtained when such CuPc derivatives are added in the acid pasting process, which leads to an improved contrast ratio of the resultant color filter prepared from the pigment particles.
  • CuPc particles substituted by at least one functional group are added during the kneading or heating step as well as in the acid pasting step. For example, CuPc particles substituted by at least one functional group selected from -SO3H, -SO2NHR1 and
  • Ri is hydrogen, alkyl, alkenyl, aryl or
  • cycloalkyl preferably , may be present in dissolution step (a) while CuPc particles substituted by -SO3H may be further added during the kneading or heating step, particularly during the kneading step.
  • the present invention is also related to alpha crystal form copper phthalocyanine particles obtainable according to the process of the present invention.
  • This embodiment is directed to the use of the copper phthalocyanine particles obtainable according to the process of the present invention for the preparation of copper phthalocyanine particles exhibiting the epsilon crystallographic form.
  • a color filter comprising copper phthalocyanine particles exhibiting the epsilon crystallographic form obtainable by the process of the present invention.
  • Example 1 (Acid-pasting beta-CuPc and phthaloimidomethyl-CuPc)
  • Example 2 (Acid-pasting beta-CuPc and monosulfonated-CuPc)
  • Copper phthalocyanine particles exhibiting alpha crystallographic form were obtained in an identical manner to that of Example 1 , except that 1 g of monosulfonated-CuPc particles was added instead of phthaloimidomethyl-CuPc particles.
  • Example 3 (Acid-pasting beta-CuPc and monosulfonated- and phthaloimidomethyl-CuPc particles)
  • Copper phthalocyanine particles exhibiting alpha crystallographic form were obtained in a manner identical to that of Example 1 , except that 0.5g of monosulfonated-CuPc particles and 0.5g of phthaloimidomethyl-CuPc particles were added instead of 1g of phthaloimidomethyl-CuPc particles.
  • Copper phthalocyanine particles exhibiting alpha crystallographic form were obtained in an identical manner to that of Example 1 , except that no CuPc derivative was added. Upon analyzing some dried samples of the resultant copper phthalocyanine particles exhibiting alpha crystallographic form with the transmission electron microscope (TEM), they were shown to have a mean particle size of more than 140 ⁇ m ( Figure 3).
  • TEM transmission electron microscope
  • the average particle size of the resultant alpha-CuPc particles using the process of the invention is significantly less than that prepared by the conventional acid pasting process (comparative example 1), i.e., more than 140 ⁇ m.
  • the kneading time can be significantly reduced while the dispersibility of the resultant particles can be improved.
  • Example 4 (Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form)
  • 50 g of the copper phthalocyanine particles exhibiting an alpha crystallographic form, obtained from example 1 or 2 and 12 g of the epsilon-type copper phthalocyanine are added with 80 g of diethylene glycol and 400 g of sodium chloride.
  • the mixture is kneaded for 2 hours at 13O 0 C with the rotation speed of 50 rpm (1 st stage), and then for 8 hours at 80 0 C with the identical rotation speed (2 nd stage).
  • the resultant particles are purified by filtration and dried at temperature of 8O 0 C and pressure of 10 4 Pa.
  • Example 5 Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form in the presence of monosulfonated- CuPc
  • Copper phthalocyanine particles exhibiting an epsilon crystallographic form were obtained in a manner identical to that of Example 4 from alpha- CuPc obtained from Example 3. However, prior to the kneading step, the alpha crystal form copper phthalocyanine and the epsilon-type copper phthalocyanine were treated at 130°C for 2 hours in diethylene glycol instead of 1 st stage and 6.2g of MS-CuPc were added during the kneading step.
  • Example 6 Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form in the presence of monosulfonated- CuPc
  • Copper phthalocyanine particles exhibiting an epsilon crystallographic form were obtained in a manner identical to that of Example 4 from alpha- CuPc obtained from Example 1. However, prior to the kneading step, the alpha crystal form copper phthalocyanine and the epsilon-type copper phthalocyanine were treated at 130°C for 2 hours in diethylene glycol instead of 1 st stage and 6.2g of MS-CuPc were added during the kneading step.
  • Example 7 Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form in the presence of monosulfonated- CuPc
  • Copper phthalocyanine particles exhibiting an epsilon crystallographic form were obtained in a manner identical to that of Example 4 from alpha- CuPc obtained from Example 1 , except that 6.2g of MS-CuPc were added during the kneading step.
  • Example 8 Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form in the presence of cetyltri methyl ammonium monosulfo CuPc
  • Copper phthalocyanine particles exhibiting an epsilon crystallographic form were obtained in a manner identical to that of Example 4 from alpha- CuPc obtained from Example 1 , except that 6.2g of cetyltrimethyl ammonium monosulfo CuPc were added during the kneading step.
  • Comparative Example 2 Crystal phase conversion of copper phthalocyanine from alpha crystal form to epsilon crystal form while adding PIM-CuPc and MS-CuPc
  • Copper phthalocyanine particles exhibiting an epsilon crystallographic form were obtained in an identical manner to that of Example 4, from alpha-CuPc obtained from comparative example 1 , except that PIM-CuPc and MS-CuPc were sequentially added during the kneading step.
  • Example 5 when color filters were fabricated from Example 5 (where PIM-CuPc and MS-CuPc were added in the acid- pasting step while MS-CuPc was further added in the kneading step), they yielded better results in contrast ratio and brightness compared to Example 6 (where PIM-CuPc alone was added in the acid-pasting step while MS-CuPc was further added in the kneading step).
  • Example 7 (utilizing MS-CuPc) also yielded improved results compared to those of Example 8 (utilizing cetyltrimethyl ammonium monosulfo CuPc).
  • Fig. 1 is an image from a Transmission Electron Microscope (TEM) for the copper phthalocyanine particles exhibiting alpha crystallographic phase prepared by the method according to Example 1.
  • Fig. 2 is an image from a TEM for the copper phthalocyanine particles exhibiting alpha crystallographic phase prepared by the method according to Example 2.
  • Fig. 3 is an image from a TEM for the copper phthalocyanine particles exhibiting alpha crystallographic phase prepared by the method according to Comparative Example 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optical Filters (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un procédé de préparation de particules de phtalocyanine de cuivre (CuPc) présentant une forme cristallographique alpha, qui comprend les étapes suivantes : (a) le mélange de particules de phtalocyanine de cuivre brutes contenant au moins 50 % en poids de particules qui présentent une forme cristallographique bêta avec un acide en présence de particules de CuPc substituées par au moins un groupe fonctionnel, de manière à ce qu'au moins une partie de la CuPc brute se dissolve dans l'acide ; et (b) la précipitation d'au moins une partie de la CuPc dissoute dans un milieu. L'ajout de dérivés de CuPc dans l'étape d'empâtage par un acide pour la conversion de phase du type cristallographique de CuPc de bêta en alpha permet d'améliorer la durée globale du procédé de fabrication de pigments bleus à base d'epsilon-CuPc, ainsi que les performances du pigment pour filtres colorés les contenant.
PCT/EP2010/053184 2009-03-18 2010-03-12 Procédé de préparation de particules de phtalocyanine de cuivre présentant une forme cristallographique alpha Ceased WO2010105982A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2012500196A JP2012520914A (ja) 2009-03-18 2010-03-12 アルファ結晶形態を示す銅フタロシアニン粒子を製造する方法
CN201080012409.5A CN102356130B (zh) 2009-03-18 2010-03-12 制备呈现α晶形的酞菁铜颗粒的方法

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Application Number Priority Date Filing Date Title
EP09155545.8 2009-03-18
EP09155545 2009-03-18

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WO2010105982A2 true WO2010105982A2 (fr) 2010-09-23
WO2010105982A3 WO2010105982A3 (fr) 2010-12-09

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JP (2) JP2012520914A (fr)
KR (1) KR20110134478A (fr)
CN (1) CN102356130B (fr)
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WO (1) WO2010105982A2 (fr)

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KR102243520B1 (ko) * 2019-11-20 2021-04-21 포항공과대학교 산학협력단 신규 프탈로시아닌 나노 와이어 및 이의 용도
CN116218255A (zh) * 2023-01-16 2023-06-06 双乐颜料股份有限公司 一种生产低氯代酞菁蓝的方法

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JP2015143368A (ja) 2015-08-06
TWI466956B (zh) 2015-01-01
KR20110134478A (ko) 2011-12-14
TW201100497A (en) 2011-01-01

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