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WO2005092988A1 - Pigment de cyanine - Google Patents

Pigment de cyanine Download PDF

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Publication number
WO2005092988A1
WO2005092988A1 PCT/JP2005/005191 JP2005005191W WO2005092988A1 WO 2005092988 A1 WO2005092988 A1 WO 2005092988A1 JP 2005005191 W JP2005005191 W JP 2005005191W WO 2005092988 A1 WO2005092988 A1 WO 2005092988A1
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WO
WIPO (PCT)
Prior art keywords
group
light
cyanine dye
ion
cyanine
Prior art date
Application number
PCT/JP2005/005191
Other languages
English (en)
Japanese (ja)
Inventor
Yasushi Aizawa
Yoshinori Koyama
Ayashi Noguchi
Original Assignee
Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
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 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo filed Critical Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority to JP2006511468A priority Critical patent/JPWO2005092988A1/ja
Publication of WO2005092988A1 publication Critical patent/WO2005092988A1/fr

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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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/20—Monoazo compounds containing cobalt
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
    • G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
    • G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
    • G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
    • G11B7/2495—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds as anions

Definitions

  • the present invention relates to a cyanine dye, and in particular, absorbs short-wavelength visible light.
  • the properties that the organic dye compound to be applied to such an application should have include good absorption properties in a short wavelength visible region, good light fastness, and good solubility in a solvent. Then, it is possible to exhibit thermal characteristics according to the use.
  • Typical organic dye compounds proposed so far include, for example, anthraquinone dyes, phthalocyanine dyes, cyanine dyes and the like (see, for example, JP-A-11-116611 and JP-A-2002-202592).
  • anthraquinone dyes have difficulty in light absorption properties
  • phthalocyanine dyes have difficulty in both light absorption properties and solubility in solvents.
  • cyanine dyes have been reported to have good light fastness and thermal properties, although they have good light absorption properties and solubility.
  • the present invention has been developed to absorb short-wavelength visible light, exhibit excellent light resistance and solubility in a solvent, and meet the needs of a new field to which an organic dye compound is applied. It is an object of the present invention to provide a novel organic dye compound having both thermal characteristics and to broaden the range of organic dye compounds that can be selected as a light-absorbing material in the fields described above. Disclosure of the invention
  • cyanine dyes which have been conventionally considered to have poor light fastness and thermal properties.
  • monomethine-based cyanine dyes having an indolenine ring at both ends of the monomethine chain and having an azo metal complex bonded as a counter ion have excellent light resistance and are purple to green.
  • such a cyanine dye absorbs visible light of a short wavelength to block it, or requires an organic dye compound having such properties as a novel light-absorbing material utilizing the energy of visible light. It has been found that it can be used advantageously in a wide variety of fields.
  • the present invention solves the above-mentioned problems by providing a cyanine dye represented by the general formula 1.
  • Z 1 represents a monocyclic aromatic ring
  • Z 2 represents a monocyclic or condensed polycyclic aromatic ring
  • the aromatic ring has a substituent.
  • R 1 to R 6 represent the same or different aliphatic hydrocarbon groups, and these aliphatic hydrocarbon groups may have a substituent.
  • the present invention relates to a cyanine dye represented by the general formula 1.
  • z 1 represents, for example, a monocyclic aromatic ring such as a benzene ring
  • z 2 represents, for example, a monocyclic or condensed polycyclic ring such as a benzene ring, a naphthalene ring, an azulene ring, and a fluorene ring.
  • an aromatic ring of the formula may have one or more substituents, and examples of the individual substituents include a methyl group, an ethylene group, a propyl group, an isopropyl group, Isopropenyl group, 1_propenyl group, 2_propenyl group, 2_propynyl group, butyl group, isobutyl group, sec-butyl group, tert_butyl group, 2-butenyl group, 1,3-butadienyl Group, pentyl group, isopentyl group, neopentyl group, tert_pentyl group, 1-methylpentyl group, 2-methylpentyl group, aliphatic hydrocarbon group such as 2-penten-4-ynyl group, cyclopropyl group, Alicyclic hydrocarbon group such as cyclobutyl group, cyclopentyl group,
  • R 1 to R 6 in the general formula 1 represent the same or different aliphatic hydrocarbon groups, and those aliphatic hydrocarbon groups may have one or more substituents.
  • the aliphatic hydrocarbon group for R 1 to R 6 include a methyl group, an ethyl group, a propyl group, an isopropylinyl group, an isopropyl group, an ⁇ _propenyl group, a 2_propenyl group, a 2_ Propynyl group, butynole group, isobutyl group, sec-butyl group, tert-butyl group, 2-butenyl group, 13-butadenino group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 2_pentene Straight or branched ones having up to 5 carbon atoms such as 4-ynyl group; and one or more hydrogen atoms
  • the bonding position of the two nitro groups in the anion of the azo metal complex may be any of the ortho, meta, and para positions with respect to the azo group.
  • the meta position is preferred.
  • the chain length of R 3 to R 6 depends on the type of the solvent, but for example, in an organic solvent, generally, the solubility increases as the number of carbon atoms increases.
  • Specific examples of the cyanine dye according to the present invention include those represented by Chemical Formulas 1 to 8. All of these have a major absorption maximum in the solution state at wavelengths longer than 400 nm, usually in the violet to green region around 430 to 550 nm, and have a molecular extinction coefficient of 1 ⁇ 10 4 or more at the absorption maximum wavelength. Since it is as large as 5 ⁇ 10 4 or more, it is possible to efficiently absorb visible light in the green range of Shino Toshi.
  • a compound represented by general formula 2 having Z 1 Z 2 , R 1 and R 2 corresponding to general formula 1 and a compound corresponding to general formula 1 By reacting the compound represented by the general formula 3 having R 3 to R 6 , the cyanine dye of the present invention represented by the general formula 1 can be synthesized at a high yield.
  • X 1 in the general formula 2 is, for example, fluorine ion, chloride ion, bromide ion, iodine ion, fluorate ion, chlorate ion, bromate ion, iodate ion, perchlorate ion, phosphate ion, hexafluoride ion.
  • Inorganic acid ions such as fluorinated phosphate ion, antimony hexafluoride ion, stannate hexafluoride ion, borofluoride ion, and tetrafluoroborate ion, thiocyanate ion, benzenesulfonate ion, naphthalenesulfonate ion, Organic acid ions such as naphthalenedisulfonic acid ion, benzene carboxylic acid ion, alkyl carboxylic acid ion, trihaloalkyl carboxylic acid ion, alkyl sulfate ion, trihaloalkyl sulfate ion, nicotinic acid ion, tetracyanoquinodimethane ion, etc.
  • X 2 in the general formula 2 is, for example, Appropriate cations including onium ions such as killammonium ions,
  • each of the compounds represented by the general formulas 2 and 3 in a reaction vessel, dissolve in a solvent as appropriate, and heat or reflux by heating or the like.
  • the solvent include hydrocarbons such as pentane, hexane, cyclohexane, petroleum ether, octane, petroleum benzene, isooctane, benzene, toluene, and xylene; carbon tetrachloride; chlorophonolem; Halides such as dichloroethane, 1,2-dibromoethane, trichloroethylene, tetrachloroethylene, chlorobenzene, bromobenzene, and dichlorobenzene, methanol, ethanol, 2,2,2_trifluoroethanol, 1_propanol, 2_propanol, 1-butanol, 2-butanol, isobutyl alcohol, isopentino
  • the cyanine dye thus obtained may be used as a reaction mixture depending on the application. However, usually, prior to use, for example, dissolution, liquid separation, gradient, filtration, extraction, concentration, thinning, and the like. Purified by general-purpose methods for purifying related compounds such as layer chromatography, column chromatography, gas chromatography, high-performance liquid chromatography, distillation, sublimation, crystallization, etc., and these methods can be combined as necessary. Applied. Depending on the type and use of the cyanine dye, high-purity organic dye compounds are required.For example, when applied to information recording or solar power generation, prior to use, for example, distillation, sublimation, etc. It is desirable to purify by a method such as crystallization.
  • the cyanine dye according to the present invention has a main absorption maximum in the solution state at a wavelength longer than 400 nm, usually in the violet to green region around 430 to 550 nm, and a molecular extinction coefficient at the absorption maximum wavelength (
  • the molecular extinction coefficient at the absorption maximum wavelength may be abbreviated as “ ⁇ ”.) Is also as large as 1 ⁇ 10 4 or more, usually 5 ⁇ 10 4 or more, so that visible light in such a wavelength range can be efficiently emitted. Absorb.
  • the cyanine dye according to the present invention is frequently used in various fields including, for example, information recording and solar power generation.
  • amide, alcohol, ketone, nitrile, and halogen-based organic solvents are used.
  • it has excellent thermal properties such as a melting point exceeding 200 ° C and a decomposition point.
  • the melting point and decomposition point of an organic compound are regarded as one of the important indicators of thermal characteristics, and it is said that the higher the melting point and decomposition point, the greater the thermal stability.
  • the melting point and decomposition point of an organic compound such as a cyanine dye can be determined by, for example, general-purpose differential scanning calorimetry (hereinafter abbreviated as "DSC analysis").
  • the cyanine dye of the present invention absorbs short-wavelength visible light to block it, or as a light-absorbing material that utilizes the energy of visible light, for example, information recording, printing, printed circuits, solar circuits, and the like. It is extremely useful in a wide variety of fields, including photovoltaic power generation, electromechanical equipment, telecommunications equipment, optical equipment, clothing, bedclothes, health care products, and agricultural materials. That is, the cyanine dye according to the present invention is useful as a photographic material in the field of information recording, and also absorbs short-wavelength visible light, and is used in optical cards, plate making, thermal transfer recording, thermal recording, and the like.
  • cyanine dyes of the present invention have a maximum absorption wavelength, for example, a gas laser such as an argon ion laser, a krypton ion laser, a helium-neon laser, a semiconductor laser such as a CdS laser, a distributed feedback type or a Bragg reflection type.
  • a gas laser such as an argon ion laser, a krypton ion laser, a helium-neon laser, a semiconductor laser such as a CdS laser, a distributed feedback type or a Bragg reflection type.
  • Printed circuit fields such as etching resist ink, plating resist ink, solder resist ink, and character ink; electrophotographic fields such as copiers, facsimile machines, and printers; optical surface mounting technology (optical SMT); self-forming connections It is extremely useful in the field of optical wiring such as technology (optical soldering), and in various fields of paints, adhesives, packaging materials, and dental materials.
  • a sensitizer for example, in the field of photovoltaic power generation, when a cyanine dye according to the present invention is supported on a semiconductor electrode of a dye-sensitized wet-type solar cell, a semiconductor for short-wavelength visible light is used.
  • the sensitivity of the electrode is improved, and the photoelectric conversion efficiency of the solar cell can be significantly improved.
  • the cyanine dye according to the present invention exhibits practically no light hindrance to environmental light such as natural light and artificial light, so that the solar cell using the cyanine dye according to the present invention as a photosensitizer can be used for a long time. Even if it is used, there is a practical advantage that the electromotive force caused by the photosensitizer is hardly reduced.
  • a filter material for example, to an image pickup tube, a semiconductor light receiving element, an optical fiber, or the like
  • the light is applied to visible light. It can reduce the rise in ambient temperature due to noise and radiated heat rays, and can adjust the visibility to a desired level. There is benefit.
  • Another application as a filter material is in the field of agricultural materials, for example, by applying it to glass plates for greenhouses or plastic substrates for vinyl nose in the form of sheets or films to produce fruit trees and grains. By controlling the wavelength distribution of light reaching useful plants such as ornamental plants such as vegetables and flowers, horticultural plants, edible plants, and medicinal plants, the growth of plants can be controlled.
  • a cyanine dye according to the present invention and, if necessary, one or more other materials that absorb light in the ultraviolet, visible, and / or infrared regions, together with a light-shielding agent and a heat ray blocking agent
  • clothing such as thermal insulation, heat storage fiber, heat-retaining fiber, or fiber having a simulated performance against reconnaissance by ultraviolet light, visible light, infrared light, etc.
  • clothing other than clothing such as drape, Pleated, shirred, lace, casement, printed, Venetian 'blind, Lonore' screen, Roman 'shade, shirt, goodwill, blanket, futon, futon, duvet cover, sheets, cushion, pillow, pillowcase, cushion, Mats, carpets, sleeping bags, window glass, window glass, buildings, vehicles, trains, ships, aircraft and other interior materials
  • the cyanine dye of the present invention can be used for positioning a tamper-proof ink, a tamper- and forgery-prevention barcode ink, a light-absorbing ink, a light-absorbing paint, a photograph and a film, similarly to the conventionally known organic dye compounds that absorb visible light. Marking agents, dyeing agents for sorting when recycling plastics, preheating aids for molding PET bottles, and visible It is useful as an active ingredient in pharmaceuticals for treating tumors generally known to be sensitive to light, and as an ingredient that helps the active ingredient to work.
  • the cyanine dye according to the present invention has remarkable light resistance to environmental light such as natural light and artificial light, but when the cyanine dye according to the present invention is used for the above-mentioned applications, for example, laser light or the like is used.
  • a so-called light resistance improver (Taenchia) is used. It does not preclude the use of multiple or multiple uses.
  • Examples of the light fastness improver used in combination with the cyanine dye according to the present invention include, for example, a re-published patent WO00Z075111 by the same patent applicant, edited by the Japan Society of Color Material, “Handbook of Color Material Engineering”, first edition, 1,274- 1, 282, Asakura Shoten Co., Ltd., published on November 25, 1989, Aminyi described in Masahiro Shinkai et al., "Dyes and Chemicals", Vol. 37, No. 7, pages 185 to 197 (1992).
  • the amount of the light fastness improver used in combination is usually 1% by mass or more, preferably 3 to 30% by mass, based on the cyanine dye.
  • the cyanine dye of the present invention is uniformly mixed with the lightfastness improver in advance and applied to a target article in the form of a liquid, semi-solid or solid composition.
  • each of them is liquid, semi-solid or solid, and individually applied to a target article.
  • the cyanine dye of this example showed a decomposition point at about 253 ° C, indistinguishable from the melting point.
  • the cyanine dye of this example was found to be chloroform, N, N-dimethylformamide, methanol, 2,2,3,3- Amides such as tetrafluoro-1-propanol (hereinafter abbreviated as "TFP"), ethynolemethinoleketone, acetonitrile, and chloroform, alcohols, ketones, nitriles, and halogens Demonstrated practical solubility in organic solvents.
  • TFP tetrafluoro-1-propanol
  • the 1 H_nuclear magnetic resonance spectrum of the cyanine dye of this example in a black form-d solution was measured, and the diagonal shift ⁇ (ppm, TMS) force was 0.000 (t, 12H), 1 50 (s, 12H), 3.06 (s, 6H), 3.17 (m, 6H), 5.17 (s, 1H), 5.87 (d, 2H), 6.13 to 6 17 (m, 2H), 6.32 (d, 2H), 7.11 (d, 2H), 7.26 to 7.34 (m, 6H), 7.56 (d, 2H), 7. Peak forces S were observed at positions 34 to 7.66 (m, 4H) and 9.18 (d, 2H).
  • the cyanine dye of the present example efficiently absorbs short-wavelength visible light, and has high solubility in a solvent and high heat. Due to its excellent properties, for example, in various fields such as information recording, photovoltaic power generation, electromechanical equipment, telecommunications equipment, optical equipment, clothing, bedclothes, health supplies, and agricultural materials, It is useful as a light-absorbing material that blocks visible light or absorbs the energy of visible light by absorbing short-wavelength visible light.
  • the cyanine dyes according to the present invention have slightly different preparation conditions and yields depending on the structure. However, for example, all of them include those represented by Chemical Formulas 1 to 8 other than those described above. Or a desired amount can be obtained according to the method.
  • the transmittance (T) of the cyanine dye at the absorption maximum wavelength (about 450 nm) was measured for a thin film.
  • the cyanine dye of the present invention in which the cation of the monomethine-based cyanine dye and the anion of the azo metal complex having a specific structure are bonded to the body, has a specific structure.
  • an anion other than the anion due to the metal complex as a counter ion for example, an analogous compound represented by chemical formula 9, or a simple mixture of such an analogous compound and, for example, an azo metal complex represented by chemical formula 10 It shows that the light resistance in the visible region is much better than that of.
  • the cyanine dye of the present invention has excellent light fastness, efficiently absorbs short-wavelength visible light, and exhibits solubility that does not hinder practical use in various organic solvents. As it has excellent properties, it absorbs short-wavelength visible light to block it, or as a light-absorbing material that uses the energy of visible light, such as information recording, solar power generation, and electromechanical devices. It is extremely useful in a wide variety of fields, including telecommunications equipment, optical equipment, clothing, bedclothes, health goods, and agricultural materials.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Indole Compounds (AREA)

Abstract

Un pigment de cyanine qui présente une structure spécifique et montre un maximum principal local en termes de spectre d'absorption de celui-ci à une longueur d'onde supérieure à 400 nm à l'état liquide. Le pigment de cyanine absorbe la lumière visible présentant une courte longueur d'onde, est excellent en termes de résistance à la lumière et de solubilité à un solvant, et, en plus de ce qui précède, présente également des caractéristiques thermiques respectant des exigences de nouveaux domaines dans lesquels sont appliqués des composés de pigments organiques, ce qui résulte dans l'expansion de la largeur des composés de pigments organiques pouvant être sélectionnés en tant que matériaux d'absorption de lumière dans les domaines mentionnés ci-dessus.
PCT/JP2005/005191 2004-03-26 2005-03-23 Pigment de cyanine WO2005092988A1 (fr)

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Application Number Priority Date Filing Date Title
JP2006511468A JPWO2005092988A1 (ja) 2004-03-26 2005-03-23 シアニン色素

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JP2004091178 2004-03-26
JP2004-091178 2004-03-26

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WO2005092988A1 true WO2005092988A1 (fr) 2005-10-06

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TW (1) TW200531993A (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006123786A1 (fr) * 2005-05-20 2006-11-23 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant a base de cyanine et support d’enregistrement optique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998029257A1 (fr) * 1996-12-27 1998-07-09 Tdk Corporation Support d'enregistrement optique
WO2001044374A1 (fr) * 1999-12-17 2001-06-21 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant de cyanine
WO2002050210A1 (fr) * 2000-12-19 2002-06-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Agent absorbeur de lumiere

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4754698B2 (ja) * 2000-02-10 2011-08-24 株式会社林原生物化学研究所 シアニン色素
JP2001232945A (ja) * 2000-02-25 2001-08-28 Fuji Photo Film Co Ltd 光情報記録媒体及び情報記録方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998029257A1 (fr) * 1996-12-27 1998-07-09 Tdk Corporation Support d'enregistrement optique
WO2001044374A1 (fr) * 1999-12-17 2001-06-21 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant de cyanine
WO2002050210A1 (fr) * 2000-12-19 2002-06-27 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Agent absorbeur de lumiere

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006123786A1 (fr) * 2005-05-20 2006-11-23 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Colorant a base de cyanine et support d’enregistrement optique

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TW200531993A (en) 2005-10-01
JPWO2005092988A1 (ja) 2008-02-14

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