WO2001028965A1 - Composition de fluoroalcool - Google Patents

Composition de fluoroalcool Download PDF

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Publication number
WO2001028965A1
WO2001028965A1 PCT/JP2000/007317 JP0007317W WO0128965A1 WO 2001028965 A1 WO2001028965 A1 WO 2001028965A1 JP 0007317 W JP0007317 W JP 0007317W WO 0128965 A1 WO0128965 A1 WO 0128965A1
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WO
WIPO (PCT)
Prior art keywords
dyes
solvent composition
dye
solvent
resin
Prior art date
Application number
PCT/JP2000/007317
Other languages
English (en)
Japanese (ja)
Inventor
Fumihiko Yamaguchi
Eiji Ogura
Toshiyuki Katsube
Original Assignee
Daikin Industries, Ltd.
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 Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2001028965A1 publication Critical patent/WO2001028965A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/38—Halogenated alcohols containing only fluorine as halogen
    • 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
    • G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers

Definitions

  • the present invention relates to a solvent composition suitably used for producing an information recording medium such as an optical disk such as a CD-R and a DVD-R.
  • some dyes have low solubility in fluoroalcohol, and some dyes have low solubility in fluoroalcohol due to the combination of the dye or the combination of the dye and quencher. In this case, it is not suitable for manufacturing an information recording medium.
  • some solvents such as hydrocarbons, alcohols, ethers, ketones, and esters, which are general-purpose solvents, dissolve pigments having low solubility in fluoroalcohol, pigment compositions or pigment quencher compositions well, They have a large property of dissolving or swelling the resin substrate of the information recording medium, and are difficult to use.
  • An object of the present invention is to provide a solvent having higher color solubility without adversely affecting a substrate of an information recording medium.
  • a solvent composition in which an organic solvent having a specific SP is mixed with fluoroalcohol has a low solubility in fluorine alcohol at a specific mixing ratio.
  • the composition or the dye quencher composition was dissolved well, and furthermore, it was found that the effect of the information recording medium on the substrate was within an allowable range.
  • the present invention provides a solvent composition, an information recording medium, and a dye solution according to the following items 1. to 9.
  • Item 2 The composition according to Item 1, comprising the fluoroalcohol in an amount of 30 mass% to 99 mass%.
  • Item 3 The solvent composition according to Item 1, wherein the organic solvent has a boiling point of 30 to 250 ° C.
  • the organic solvent is acetonitrile, HCFC141b (l, l-dichloro-1,6-fluoroethane), CFC113 (1,1,2-trichloro-1,2,2-trifluoroethane), DAA ( Diacetone alcohol), acetone, isophorone, methanol, ethanol, 1-propanol, 1-butanol, dimethyl ether, diisopropyl ether, THF, ethylene glycol dimethyl ether, ethylene glycol dimethyl ether, ethylene glycol Monomethyl ether, ethylene glycol monoethyl ether, MEK, methyl isobutyl ketone, cyclohexanone, DMF, n-hexane, n-heptane, n-octane, n-decane, n-dodecane, cyclohex
  • Item 5 The solvent composition according to Item 1, wherein the rate of change in land width (convex portion) when the resin-made information recording medium substrate is pulled up and air-dried immediately after immersion is within 10% of the land width before immersion. .
  • Item 6 The solvent composition according to Item 5, wherein the material of the resin-made information recording medium is at least one selected from the group consisting of polycarbonate resin, acrylic resin, vinyl chloride resin, epoxy resin, amorphous polyolefin and polyester.
  • Item 7 An information recording medium produced by using the solvent composition according to Item 1, wherein a recording layer on which information can be written and Z or readable by a laser is provided on a substrate.
  • Item 8 A dye solution of the solvent composition according to Item 1.
  • the dye is a cyanine dye, a phthalocyanine dye, an azo dye, a pyrylium dye, a thiopyrylium dye, a squarylium dye, an azurenium dye, an indophenol dye, an indoline phosphorus dye, or a triphenyl methane.
  • Dyes Item 9. The dye solution according to Item 8, which is at least one selected from the group consisting of a non-dye, an amine dye, a diimmonium dye, and a metal complex dye.
  • Examples of the organic solvent blended in the solvent composition of the present invention include aliphatic saturated alcohols having 1 to 4 carbon atoms (for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, Organic solvents excluding sec-butanol and t-butanol are preferred.
  • the organic solvent to be blended in the solvent composition of the present invention and the S.P. and boiling point of the organic solvent are shown below.
  • n 1 can 6.6 174.12
  • the S.P. (solubility parameter) of the organic solvent is about 4 to about 20, preferably about 6 to about 15.
  • the boiling point of the organic solvent blended in the solvent composition of the present invention is preferably from about 30 to about 250.
  • the solubility of the solvent composition of the present invention with respect to the dye is 25, preferably about 1.3 mass%, more preferably about 3.5 mass% or more.
  • the fluoroalcohol of formula (1) is preferably from about 30 to about 99 mass%, more preferably from about 70 to about 95 mass%.
  • the evaporation residue of the solvent composition obtained in the present invention is about 5 Omass ppm or less, preferably about 25 mass ppm or less, more preferably about 1 Omass ppm or less.
  • the evaporation residue can be determined as follows. That is, the weight of the residue when the solvent composition of the present invention was evaporated at 40 ° 6.7 ⁇ 10 2 Pa was measured, and HCF 2 CF Expressed as mass ppm relative to 2 CH 2 OH.
  • Absorbance in methanol at 2 0 5 nm of the solvent composition of the present invention is from about 0 1 abs or less, preferably about -.. 0 l abs or less, more preferably about -. 0 c Methanol is 2 abs or less
  • the absorbance in the medium is measured by using a sample obtained by adding 3 ml of methanol to lm 1 of the solvent composition of the present invention as a measurement sample and using methanol as a reference.
  • the solvent composition of the present invention is "substantially free of impurities" it means that U) the residue of evaporation of the fluorine alcohol is about 50 mass ppm or less, preferably about 25 mass ppm or less, more preferably Is about 1 O mass ppm or less, and Z or (ii) the absorbance (205 nm) in methanol is about 0.1 abs or less, preferably about _0.1 abs or less. It preferably means less than about 0.2 abs.
  • the solvent composition of the present invention has a land width (convex portion) of about 90% to about 110% before immersion when the polycarbonate information recording medium substrate (for example, a CD-R substrate) is immediately pulled up and air-dried after immersion. Preferably it is from about 95 to about 105%.
  • the land width (convex portion) can be confirmed by an electron micrograph.
  • An information recording medium provided with a recording layer on which information can be written by a laser beam and Z or readable by a laser is provided on a substrate, comprising a solvent containing a fluorine alcohol of the general formula (1) of the present invention, preferably the fluorine alcohol.
  • the dye can be dissolved in a fluorine-containing solvent, and the resulting solution can be applied onto a substrate and dried to form a recording layer containing the dye, according to a conventional method.
  • the dye examples include a cyanine dye, a phthalocyanine dye, an azo dye, a pyrylium dye, a thiopyrylium dye, a squarylium dye, an azurenium dye, an indophenol dye, an indoline phosphorus dye, and a triphenylmethane dye.
  • quinone dyes amidium dyes, diimmonium dyes, metal complex dyes, and the like.
  • Preferred dyes are cyanine dyes, phthalocyanine dyes and azo dyes.
  • a quencher for preventing deterioration or decomposition of the dye at the time of manufacturing and storing the information recording medium or at the time of recording and reproducing information may be used in combination with the dye.
  • the substrate include plastics such as polycarbonate, polymethyl methacrylate, epoxy resin, amorphous polyolefin, polyester, and polyvinyl chloride, glass, and ceramics.
  • an undercoat layer is provided between the recording layer and the substrate for the purpose of improving flatness, improving adhesive strength, preventing deterioration of the recording layer, etc.
  • a protective layer may be provided on the recording layer.
  • the present invention is suitable for the manufacture of information recording media (such as optical discs such as CD_R and DVD-R) in which information is written by a laser and Z or a readable recording layer is provided on a substrate.
  • information recording media such as optical discs such as CD_R and DVD-R
  • a solvent composition that does not affect the substrate can be provided.
  • the fluoroalcohol use three types of HCF 2 CF 2 CH 2 OH ( TFP), HCF 2 CF 2 CF 2 CF 2 CH 2 0 H (OFP), HCF (CF 3) CF 2 CH 2 OH (HFB) did.
  • composition Type Composition
  • Table 2 shows the results.
  • Test example 1 Influence test on polycarbonate CD-R substrate A CD-R substrate (land width: 1.2 / xm) made of polycarbonate was immersed in each of the test solvents of Examples 1 to 10 and Comparative Examples 1 to 10 immediately after being immersed and dried by an electron microscope. Observations were made to determine the effect on the CD-R substrate from changes in land width. Table 2 shows the results. The effect on the CD-R substrate was evaluated according to the following criteria.
  • a dye mixture of 5 parts by weight of cyanine dye OM-57 (manufactured by Fuji Photo Film Co., Ltd.) and 2 parts by weight of dye EST-3 (Sumitomo Seika Co., Ltd.) used as quencher was prepared.
  • the saturation solubility of each of the dye mixtures of Examples 1 to 10 and Comparative Examples 1 to 10 in each test solvent was determined, and the dye solubility was determined according to the following criteria. Table 2 shows the results.
  • Example 10 ⁇ ⁇ ⁇ Comparative Example 1 ⁇ ⁇ Comparative Example 2 ⁇ ⁇ Comparative Example 3 ⁇ ⁇ ⁇ Comparative Example 4 XXX Comparative Example 5 ⁇ XX Comparative Example 6 XX Comparative Example 7 XX Comparative Example 8 ⁇ ⁇ ⁇ Comparative Example 9 ⁇ XX Comparative Example 10 ⁇ XX

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Manufacturing Optical Record Carriers (AREA)

Abstract

L'invention porte sur une composition de solvant appropriée pour être utilisée dans la fabrication d'un support d'enregistrement d'informations, y compris des disques optiques tels que CD-R et DVD-R. Cette composition a une plus grande aptitude à dissoudre les colorants et n'altère pas le substrat d'un support d'enregistrement d'informations. La composition de solvant comprend un fluoroalcool représenté par la formule (1) suivante: H(CFR1CF2)nCH2OH (dans laquelle n vaut 1 ou 2; et R1 représente F ou CF¿3? lorsque n vaut 1, et représente F lorsque n vaut 2) et un solvant organique ayant un paramètre de solubilité (PS) compris entre 4 et 20.
PCT/JP2000/007317 1999-10-22 2000-10-20 Composition de fluoroalcool WO2001028965A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP30048699A JP2001122813A (ja) 1999-10-22 1999-10-22 フッ素アルコール組成物
JP11/300486 1999-10-22

Publications (1)

Publication Number Publication Date
WO2001028965A1 true WO2001028965A1 (fr) 2001-04-26

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ID=17885398

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/007317 WO2001028965A1 (fr) 1999-10-22 2000-10-20 Composition de fluoroalcool

Country Status (4)

Country Link
JP (1) JP2001122813A (fr)
CN (1) CN1246276C (fr)
TW (1) TW513355B (fr)
WO (1) WO2001028965A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160237289A1 (en) * 2015-02-17 2016-08-18 Fu-Shing Wang Composition of coating solution and dye solvent used in information recording media

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI292150B (fr) * 2001-09-20 2008-01-01 Hayashibara Biochem Lab

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4618264B1 (fr) * 1966-11-11 1971-05-21
JPS55131099A (en) * 1979-03-30 1980-10-11 Daikin Ind Ltd Surface cleaning composition
JPS55144100A (en) * 1979-04-27 1980-11-10 Daikin Ind Ltd Surface cleaning composition
EP0272933A2 (fr) * 1986-12-23 1988-06-29 Fuji Photo Film Co., Ltd. Procédé de préparation d'un support d'enregistrement d'information
JPH0449258A (ja) * 1990-06-14 1992-02-18 Konica Corp 溶媒含有シアニン色素の製造方法
JPH04337538A (ja) * 1991-05-14 1992-11-25 Ricoh Co Ltd 光記録媒体の製造方法及び光記録媒体
JPH05225619A (ja) * 1992-02-17 1993-09-03 Ricoh Co Ltd 光記録媒体及びその製造方法
JPH11202516A (ja) * 1998-01-14 1999-07-30 Mitsubishi Chemical Corp 電子写真感光体の製造方法
WO1999062064A1 (fr) * 1998-05-27 1999-12-02 Tdk Corporation Procede permettant de produire un support d'enregistrement optique, et support d'enregistrement optique

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4618264B1 (fr) * 1966-11-11 1971-05-21
JPS55131099A (en) * 1979-03-30 1980-10-11 Daikin Ind Ltd Surface cleaning composition
JPS55144100A (en) * 1979-04-27 1980-11-10 Daikin Ind Ltd Surface cleaning composition
EP0272933A2 (fr) * 1986-12-23 1988-06-29 Fuji Photo Film Co., Ltd. Procédé de préparation d'un support d'enregistrement d'information
JPH0449258A (ja) * 1990-06-14 1992-02-18 Konica Corp 溶媒含有シアニン色素の製造方法
JPH04337538A (ja) * 1991-05-14 1992-11-25 Ricoh Co Ltd 光記録媒体の製造方法及び光記録媒体
JPH05225619A (ja) * 1992-02-17 1993-09-03 Ricoh Co Ltd 光記録媒体及びその製造方法
JPH11202516A (ja) * 1998-01-14 1999-07-30 Mitsubishi Chemical Corp 電子写真感光体の製造方法
WO1999062064A1 (fr) * 1998-05-27 1999-12-02 Tdk Corporation Procede permettant de produire un support d'enregistrement optique, et support d'enregistrement optique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160237289A1 (en) * 2015-02-17 2016-08-18 Fu-Shing Wang Composition of coating solution and dye solvent used in information recording media

Also Published As

Publication number Publication date
JP2001122813A (ja) 2001-05-08
TW513355B (en) 2002-12-11
CN1479708A (zh) 2004-03-03
CN1246276C (zh) 2006-03-22

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