WO2008038679A1 - Composé phtalocyanine et son procédé de production - Google Patents

Composé phtalocyanine et son procédé de production Download PDF

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Publication number
WO2008038679A1
WO2008038679A1 PCT/JP2007/068715 JP2007068715W WO2008038679A1 WO 2008038679 A1 WO2008038679 A1 WO 2008038679A1 JP 2007068715 W JP2007068715 W JP 2007068715W WO 2008038679 A1 WO2008038679 A1 WO 2008038679A1
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Prior art keywords
group
substituent
phthalocyanine compound
phthalocyanine
reaction
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PCT/JP2007/068715
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English (en)
Japanese (ja)
Inventor
Yohei Makimoto
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Nippon Shokubai Co., Ltd.
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Publication of WO2008038679A1 publication Critical patent/WO2008038679A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • 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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0671—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton
    • 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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
    • 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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0676—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having nitrogen atom(s) linked directly to the skeleton
    • 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
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • Phthalocyanine compound and method for producing the same
  • the present invention relates to a phthalocyanine compound, particularly a phthalocyanine mixture, particularly a phthalocyanine mixture and a method for producing the same, having a selective absorption ability in the near-infrared wavelength region of UOOnm, solubility in a hydrophilic solvent, and water solubility.
  • the phthalocyanine compound (phthalocyanine mixture) of the present invention is a color toner, inkjet ink, household inkjet ink, anti-counterfeiting barcode ink, goggles lens or shielding plate, and dyeing for sorting during plastic recycling.
  • phthalocyanine compounds having excellent absorption ability and heat resistance, light resistance, and weather resistance.
  • various phthalocyanine compounds have been studied.
  • 'Except for the developed phthalocyanine for CD-R most of the conventional phthalocyanine compounds are organic solvents such as acetone, chloroform, toluene and methyl ethyl ketone. Although it is soluble in water, it is hardly soluble in lower alcohols such as methanol or their aqueous solutions or even water, and this limits the choice of the solvent used and the type of resin used. there were.
  • a 3-pyridyloxy group in the form of a pyridinium cation that imparts water solubility during protonation is introduced at the / 3-position of the phthalocyanine compound skeleton.
  • Methods have been devised (see, for example, HETEROCYCLE S, Vol. 22, No. 9, p. 2047-2052, 1984). According to the method described in HETERO CYCLES, Vol. 22, No. 9, p.
  • the target Zn ( II) Since tetra- (3-pyridyloxy) phthalocyanine is produced through a very complicated process of 7 steps, there is a disadvantage that the yield of the final product is low and economically undesirable.
  • a pyridyloxy group is added to the 3-position of the benzene ring in advance, and then the cyclization reaction is performed, so that the final product is a single structure bonded to the / 3-position of the individual phthalocyanine skeleton. Is obtained.
  • the maximum absorption wavelength of the final product is one.
  • a dye having a desired absorption wavelength is separately added. It is necessary to mix, which is also economically undesirable.
  • R 3 and R 3 may each independently have a phenyl group which may have a substituent, may have a substituent, may have a V aralkyl group or a substituent! /,
  • the number of carbon atoms; ⁇ 20 alkyl groups represented R 2 and R 3 may be the same or different from each other;
  • M represents a metal-free, metal, metal oxide or metal halide,
  • the phthalocyanine compound (1) represented by the formula is selected from the group consisting of pyridinol which may have a substituent, may have a substituent! /, Imidazole and may have a substituent, and pyrazole This is achieved by a method for producing a phthalocyanine compound having a reaction with at least one selected from the group consisting of:
  • the phthalocyanine compound (1) represented by the above formula (1) may have a substituent! /, Pyridinol, or a substituent! / It is also achieved by a phthalocyanine compound produced by reacting with at least one selected from the group consisting of imidazole and optionally substituted pyrazole.
  • the phthalocyanine compound (phthalocyanine mixture) according to the present invention is used for color toner, inkjet ink, household inkjet ink, anti-counterfeit barcode ink, goggles lens and shielding plate, and plastic recycling.
  • FIG. 1 is a diagram showing the results of liquid chromatography of the reaction product obtained in Example 1.
  • the present invention relates to a method for producing a phthalocyanine compound having a reaction with at least one selected from the group consisting of:
  • the phthalocyanine compound produced by the method of the present invention exhibits excellent hydrophilicity and / or water solubility, a hydrophilic solvent such as a lower alcohol such as methanol or ethanol or an aqueous solution thereof, and / or water Can be easily dissolved.
  • a hydrophilic solvent such as a lower alcohol such as methanol or ethanol or an aqueous solution thereof, and / or water Can be easily dissolved.
  • such a phthalocyanine compound having excellent hydrophilicity and water solubility can be produced in the form of a plurality of mixtures by a simple method.
  • the term “hydrophilic” means that the solubility in a lower alcohol having 1 to 4 carbon atoms such as methanol, ethanol, 2-ethoxyethanol or an aqueous solution thereof is 0.1% by mass or more.
  • the solubility power in these hydrophilic solvents is 1.0% by mass or more, more preferably 5.0% by mass or more.
  • water-soluble means that the solubility in water (water solubility) is 0.1% by mass or more, and preferably, the solubility in water is 1S 1.0% by mass or more. Preferably it is 5.0 mass% or more.
  • hydrophilic and / or water-soluble is also collectively referred to as “hydrophilic”.
  • a plurality of phthalocyanine compounds can be easily produced in the form of a mixture without complicated steps, and these phthalocyanine compounds can be produced. Indicate different maximum absorption wavelengths. Further, the maximum absorption wavelength of each phthalocyanine compound depends on the structure of the phthalocyanine compound (1) of the formula (1), particularly the type and number of halogen atoms shown in the formula (1), and other substituents other than the nitrogen atom. Type: May have a substituent!
  • the phthalocyanine compound and the phthalocyanine mixture according to the present invention are used in power toners, inkjet inks, household inkjet inks, anti-counterfeiting barcode inks, goggles lenses and shielding plates, and plastic recycling.
  • Various applications such as photothermal exchange agents, anti-counterfeiting of ID cards, photothermal exchange agents for laser transmission welding (LTW), heat ray shielding agents, and near-infrared absorption filters, preferably inkjet inks Ink-jet ink for home use, optical recording media, anti-counterfeit bar It can be suitably used for cord inks, goggle lenses and shielding plates, and photosensitive dyes for laser therapy, particularly ink jet inks.
  • the imidazole that may be substituted is also referred to as “imidazole derivative”, the pyrazole that may have a substituent is also referred to as “pyrazole derivative”, and the pyridinol derivative, imidazole derivative, and pyrazole derivative are also collectively referred to as “derivative”. .
  • Z to Z may be the same or different from each other.
  • M represents a metal-free, metal, metal oxide or metal halide.
  • metal-free means an atom other than a metal, for example, two hydrogen atoms.
  • examples of the metal include iron, magnesium, nickel, cobalt, copper, noradium, zinc, vanadium, titanium, indium, and tin.
  • examples of the metal oxide include titanyl and vanadyl.
  • the metal halide include aluminum chloride, indium chloride, germanium chloride, tin (II) chloride, tin (IV) chloride, and silicon chloride.
  • the phthalocyanine compound (1) by reaction of the phthalocyanine compound (1) with at least one selected from the group consisting of a pyridinol derivative, an imidazole derivative and a pyrazole derivative, part or all of the halogen atoms present in the phthalocyanine compound (1). Is replaced with the above derivative (a group derived from the above derivative is introduced at a position where a halogen atom is present), and the phthalocyanine compound obtained thereby exhibits hydrophilicity / water solubility. For this reason, the hydrophilicity / water solubility of phthalocyanine compounds depends on the number of halogen atoms in z to z.
  • the force s is preferably present in 1 4 1 2 3 2 3 4. If the number of halogen atoms is other than the above, the same number of halogen atoms are present in each benzene ring as much as possible, and the excess halogen atom force s is at least at the z-position or z-position in the benzene ring of the phthalocyanine skeleton. Like to exist
  • R 2 and R 3 represent an optionally substituted phenyl group, an optionally substituted aralkyl group, or an optionally substituted alkyl group having 1 to 20 carbon atoms. .
  • R 2 and R 3 may be the same or different! /.
  • the halogen atom that can be substituted on the phenyl group or aralkyl group includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a fluorine atom, a chlorine atom, more preferably a fluorine atom. is there.
  • acyl group examples include a acetyl group, an ethylcarbonyl group, a propylcarbonyl group, a petitenorecanolinore group, a pentinorecanoreponinole group, a hexinorecanoreponinore group, a benzoinole group, and a ptbutylbenzoyl group.
  • acetyl and ethylcarbonyl groups are preferred.
  • the alkyl group is a straight chain having a number of carbon atoms;! -20, preferably a carbon atom;!-8 A branched or cyclic alkyl group, methyl group, ethyl group, n propyl group, isopropylene group, n butyl group, isobutyl group, sec butyl group, tert butyl group, n pentynole group, isopentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexenole group, cyclohexyl group, 1,3-dimethylbutyl group, 1 isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4 dimethylpentyl group, 2 —Methyl-1 isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethyl group,
  • the rogenated alkyl group is a halogenated part of a linear, branched or cyclic alkyl group having carbon atoms;! To 20, preferably carbon atoms;! To 8 carbon atoms.
  • Examples include chloromethyl group, bromomethyl group, trifunoleolomethylenole group, chlorodiethyl group, 2,2,2-trichlorodiethyl group, bromoethyl group, clopropropyl group, and bromopropyl group.
  • the alkylcarbonylamino group includes an acetylylamino group, an ethylcarbonylamino group, an n-propylcarbonylamino group, an isopropylcarbonylamino group, an n-butylcarbonylaminoamino group, and an isobutylcarbonylamino group.
  • the arylylcarbonylamino group includes a benzoylamino group, p-chlorobenzoylamino group, p-methoxybenzoylamino group, p-t-butylbenzoylamino group, p-trifluoromethylbenzilamino group, Examples include m-trifluoromethylbenzoylamino group.
  • a phthalonitrile compound (A) represented by the following formula (3):
  • the phthalonitrile compounds (A) to (D) of the formulas (2) to (5) as the starting materials are conventionally used, such as the method disclosed in JP-A No. 64-45474.
  • the compound can be synthesized by a known method, or a commercially available product can be used, but preferably the following formula (6):
  • X, X, X and X are each independently a fluorine atom, a chlorine atom, or a bromine atom.
  • HSR 1 and HOR 3 are independently selected from the group consisting of HSR 1 and HOR ⁇ R 1 and R 3 as defined in the above formula (1).
  • the ratio of HSR 1 and HOR 3 is appropriately selected according to the structure of the target phthalonitrile compound.
  • the total amount of HSR 1 and / or HOR 3 is not particularly limited as long as these reactions can proceed to produce the desired phthalonitrile compound, but with respect to 1 mol of the phthalonitrile derivative, Usually 1.0 to 6.0 monoliths, preferably 1.1 to 2.5 monoles.
  • the phthalonitrile compound can be obtained by reacting the phthalonitrile derivative represented by the formula (6) with one or more selected from the group consisting of HSR 1 and HOR 3 .
  • the reaction between the phthalonitrile derivative and HSR 1 and / or HOR 3 may be performed in the absence of a solvent or in an organic solvent! /, But is preferably performed in an organic solvent.
  • organic solvents that can be used in this case include nitriles such as acetonitrile and benzonitrile; Examples include polar solvents such as acetone and 2-butanone. Of these, preferably acetonitrile, benzonitrile and acetone.
  • the amount of trapping agent used when using the trapping agent is not particularly limited as long as it is an amount capable of efficiently removing hydrogen halide generated during the reaction, but is usually limited to 1 mol of phthalonitrile derivative.
  • a phthalocyanine compound (1) in which all of Z to Z in the formula (1) are halogen atoms is a phthalocyanine compound (1) in which all of Z to Z in the formula (1) are halogen atoms.
  • the cyclization reaction comprises the phthalonitrile compounds (A) to (D) of formulas (2) to (5) and a metal, metal oxide, metal carbonyl, metal halide, and organic acid metal. It is preferable to react one kind selected from the group in a molten state or in an organic solvent.
  • Metals, metal oxides, metal carbonyls, metal halides and organic acid metals (hereinafter collectively referred to as “metal compounds”) that can be used at this time include those corresponding to M of the phthalocyanine compound obtained after the reaction. If it can be obtained, it is not particularly limited.
  • metals such as iron, copper, zinc, vanadium, titanium, indium and tin listed in the item M in the above formula (1), the metal Metal halide compounds such as chloride, bromide, iodide, etc., metal oxides such as vanadium oxide, titanyl oxide and copper oxide, organic acid metals such as acetate, and complex compounds such as acetylacetonate and carbo two And metal carbonyls such as iron.
  • metals, metal oxides and metal halides are preferred.
  • an equimolar amount of an amino compound having a group of the formula: NHR 2 is usually equimolar to 1 mol of a phthalocyanine compound derivative obtained by a cyclization reaction between a phthalonitrile compound (A) to (D) and a metal compound. Above, preferably 1.0 to 1.1; Next, with respect to 1 mol of the phthalocyanine compound derivative for the purpose of trapping the generated hydrogen halide, inorganic components such as calcium carbonate and calcium hydroxide are added to this reaction product; Charge the trapping agent in the range of 3-8 mol.
  • the reaction temperature and time within the above range, it is possible to control the amount of ammine to be substituted. Usually, the amount of ammine is increased or the reaction temperature is increased to tighten the reaction conditions. It is possible to increase the number of ammine substitutions.
  • the inorganic component is filtered and the amino compound is distilled off (washed) to produce a complex production of the desired phthalocyanine compound of the present invention. Without passing through the process, it is possible to obtain efficiency and high purity.
  • the substituent is not particularly limited, but an alkyl group, a halogenated alkyl group, an alkoxynole group, a halogenated alkoxyl.
  • the pyrazole derivatives include pyrazole, substituted pyrazoles having a substituent at at least one of the 3, 4, and 5 positions of the pyrazole ring, and salts thereof.
  • the substituent is not particularly limited, but is an alkyl group, a halogenated alkyl group, an alkoxyl group, a halogenated group.
  • Examples include a ruaminomethyl group, a hydroxyl group, a carboxyl group, a strong rubamoyl group, a piperidyl group, a piperidinomethyl group, a morpholino group, a morpholinomethyl group, a nitro group, a cyano group, and a halogen atom.
  • the reaction conditions of the phthalocyanine compound (1) and the derivative are not particularly limited as long as these reactions can sufficiently proceed.
  • the phthalocyanine compound (1) is reacted with the derivative at a temperature of 40 240 C, more preferably 60 200 C for 0.5-60 hours, more preferably 145 hours.
  • the reaction may be performed under normal pressure, increased pressure, or reduced pressure, but is preferably performed at normal pressure.
  • methyl chloride methyl chloride, methyl bromide, methyl bromide, methyl iodide, methyl iodide, and dimethyl sulfate are preferred.
  • Methyl chloride, methyl bromide, methyl iodide, and dimethyl sulfate are more preferred. Particularly preferred is methyl iodide.
  • Example 1 except that hexadecafluorovanadyl phthalocyanine prepared in Synthesis Example 2 was used instead of hexadecafluorozinc phthalocyanine, the same operation as in Example 1 was performed, and 1.30 g of reaction product was gotten.
  • Example 1 the same procedure as in Example 1 was used, except that hexadecafluorozinc phthalocyanine prepared in Synthesis Example 3 was used instead of hexadecafluorozinc phthalocyanine, and 0.92 g of reaction product was obtained. Obtained.
  • this solid substance was dissolved in methanol, and acetone was added to precipitate the solid content again.
  • This solid content was dissolved in 6 mL of methanol, passed through a basic Al 2 O column, and then the methanol was distilled off with an evaporator. The rest
  • Example 8 Reaction of hexadecafluorozinc phthalocyanine with 4-pyridinol (base: N-methylbiperidine and calcium carbonate)
  • reaction solution was cooled to room temperature, the precipitated solid was filtered off, and the resulting filtrate was concentrated.
  • the resulting concentrated solution was diluted with ethanol, and then acetone was added to precipitate a solid. After this solid content was dissolved in methanol, acetone was added to precipitate the solid content again.
  • the obtained solid was dried under reduced pressure at 60 ° C. to obtain 5.51 g of a reaction product.
  • the concentrated solution obtained was diluted with ethanol, and acetone was added to analyze the solid content. After this solid content was dissolved in methanol, acetone was added to precipitate the solid content again. The obtained solid content was dissolved in a mixed solvent of water and methanol, and then stirred for 30 minutes in the presence of calcium carbonate. Calcium carbonate was filtered off, and the resulting filtrate was concentrated to dryness. The obtained solid was dried under reduced pressure at 60 ° C, and 2.27 g of reaction product was obtained.
  • Example 10 2, 6, 10, 14 Tetra (2, 6 dimethylphenoxy) 1, 3, 4, 5, 7, 8, 9, 1 1, 12, 13, 15, 16 Reaction of Loa t ⁇ phthalocyanine with 4-pyridinanol (base: KF)
  • the phthalocyanine compound (including phthalocyanine mixture) according to the present invention is excellent in hydrophilicity / water solubility, color toner, inkjet ink, household inkjet ink, anti-counterfeit barcode ink, goggles Lenses, shielding plates, plastic dyes for sorting during recycling, optical recording media, photosensitive dyes for laser therapy, preheating aids during the molding of PET bottles, thermal transfer, thermal stencils, etc.
  • Photothermal heat exchanger heat-sensitive rewritable recording photothermal exchanger, ID card forgery prevention, plastic laser transmission welding (LTW: Laser Transmission Welding) photothermal exchanger, heat ray shielding agent, and near infrared absorption It can be suitably used for various applications such as filters, particularly ink jet ink. Furthermore, this application is based on Japanese Patent Application No. 2006-263 318 filed on Sep. 27, 2006, the disclosure of which is incorporated by reference and incorporated in its entirety.

Abstract

La présente invention concerne un procédé de production d'un composé phtalocyanine soluble dans un solvant hydrophile ou l'eau et utile même dans des applications dans lesquelles des composés phtalocyanine n'ont pas jamais été applicables. La présente invention concerne plus spécifiquement un procédé de production d'un composé phtalocyanine, lequel comprend la réaction d'un composé phtalocyanine (1) représenté par la formule (1) avec au moins un élément choisi dans le groupe constitué par un pyridinole pouvant avoir un substituant, un imidazole pouvant avoir un substituant et un pyrazole pouvant avoir un substituant. (1) où les groupes Z1 à Z16 représentent indépendamment un atome d'hydrogène, SR1, NHR2, OR3 ou un atome d'halogène, à condition qu'au moins deux éléments des groupes Z1 à Z16 représentent un atome d'halogène ; R1, R2 et R3 représentent indépendamment un groupe phényle pouvant avoir un substituant, un groupe aralkyle pouvant avoir un substituant ou un groupe alkyle possédant de 1 à 20 atomes de carbone pouvant avoir un substituant ; deux ou plus des groupes R1, R2 et R3 peuvent être identiques ou différents ; et M représente un élément non-métallique, un métal, un oxyde de métal ou un halogénure de métal.
PCT/JP2007/068715 2006-09-27 2007-09-26 Composé phtalocyanine et son procédé de production WO2008038679A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103319492A (zh) * 2013-07-11 2013-09-25 中国科学院化学研究所 一种制备含金属全氟酞菁衍生物的方法
WO2017130825A1 (fr) * 2016-01-29 2017-08-03 富士フイルム株式会社 Composition, film, filtre de coupure du proche infrarouge, stratifié, procédé de formation de motif, capteur d'image semiconducteur, dispositif d'affichage d'image, capteur d'infrarouges et filtre de couleur

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56129259A (en) * 1980-02-18 1981-10-09 Basf Ag Imidazolyl methylene containing dyestuff and use thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56129259A (en) * 1980-02-18 1981-10-09 Basf Ag Imidazolyl methylene containing dyestuff and use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103319492A (zh) * 2013-07-11 2013-09-25 中国科学院化学研究所 一种制备含金属全氟酞菁衍生物的方法
WO2017130825A1 (fr) * 2016-01-29 2017-08-03 富士フイルム株式会社 Composition, film, filtre de coupure du proche infrarouge, stratifié, procédé de formation de motif, capteur d'image semiconducteur, dispositif d'affichage d'image, capteur d'infrarouges et filtre de couleur
US10947389B2 (en) 2016-01-29 2021-03-16 Fujifilm Corporation Composition, film, near infrared cut filter, laminate, pattern forming method, solid image pickup element, image display device, infrared sensor, and color filter
US11518833B2 (en) 2016-01-29 2022-12-06 Fujifilm Corporation Composition, film, near infrared cut filter, laminate, pattern forming method, solid image pickup element, image display device, infrared sensor, and color filter

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