Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-07-06
1994-09-27
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D48722
Patent
active
053508432
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a halogenated alkoxyphthalocyanine which is useful as a dye, a pigment, a filter, a liquid crystal display material and a recording material. Furthermore, the present invention relates to an optical recording medium using the compound and a mixture thereof as well as a method for preparing the compound and the mixture.
BACKGROUND ART
Halogenated alkoxyphthalocyanines are disclosed in EP 0373643 and Japanese Patent Application Laid-open Nos. 197280/1986 and 85630/1975.
Techniques of using the halogenated alkoxyphthalocyanines as optical recording media are described in EP 373643, Japanese Patent Application Laid-open No. 197280/1986, U.S. Pat. No. 4,298,975, EP 353394 and U.S. Pat. No. 4,769,307. However, the optical recording media using the compounds described in the above-mentioned patents are insufficient in sensitivity, a refractive index, recording properties and reflectance.
In particular, EP 373643 discloses the phthalocyanines each having four alkoxy groups, or four alkoxy groups and four substituents. However, among the phthalocyanines disclosed in this patent, for example, the compounds shown in Examples 93 to 100 had a small refractive index of 2 or less at 780 nm and insufficient sensitivity and recording properties. On the other hand, the compounds shown in Examples 100 to 103 could not provide an industrially homogeneous recording layer, because the solubility of these compounds in a coating solvent was 10 g/l which was too low to prepare the optical recording medium therefrom in accordance with a spin coating process by the use of a polycarbonate substrate. In addition, the sensitivity, recording properties and reflectance of the media were insufficient.
With regard to the halogenation of the phthalocyanine, Publication Board Report No. 65,657 describes a method in which antimony trisulfide or aluminum chloride is used as a catalyst. However, this method could not be applied to such a phthalocyanine containing the alkoxy group as in the present invention, since the alkoxy group substituted on a benzene ring, for example, a phenyl alkyl ether decomposes in the presence of aluminum chloride into phenol and an alcohol. This decomposition reaction is described in the literatures of Chem. Ber., 76B, 900 (1943), J. Org. Chem. 27, 2037 (1962) and Chem. Ber., 93, 2761 (1960).
Furthermore, J. Org. Chem., 6, 852 (1941) and Chemical Industries, 1138 (1967) describe the decomposition reaction in which an acid byproduced in the halogenation reaction, for example, hydrogen chloride or hydrogen bromide produced at the halogenation with chlorine or bromine decomposes a phenyl ether into phenol and an alcohol.
DISCLOSURE OF THE INVENTION
A first object of the present invention is to provide a phthalocyanine compound or mixture which is useful as a recording layer for writable compact disks (abbreviate to "CD-WO") having excellent sensitivity and reflectance, a high refractive index and excellent recording properties.
A second object of the present invention is to provide a synthetic route of a halogenated alkoxyphthalocyanine compound or mixture thereof according to the present invention and optimum conditions for the synthesis.
A third object of the present invention is to provide a recording medium, particularly a CD-WO recording medium in which the halogenated alkoxyphthalocyanine compound or mixture thereof is contained in a recording layer.
The present inventors have intensively investigated with the intention of solving the above-mentioned problems, and as a result, they have found that a compound and mixture into which alkoxy groups having a large steric hindrance and halogen atoms are introduced are excellent in sensitivity, reflectance and recording properties and have a high refractive index as the CD-WO recording layer. It has also been found that the phthalocyanine compound and mixture containing the alkoxy groups in which the total number of the secondary, tertiary or quaternary carbons is from 2 to 4, and containing 1 to 4 halogen atoms, p
REFERENCES:
patent: 2214469 (1935-08-01), Linstead et al.
patent: 4948884 (1990-08-01), Nonaka et al.
patent: 5153313 (1992-10-01), Kazmaier et al.
Cook et al., J. Chem. Soc., Perk Trans. I., 1988, pp. 2453-2458.
Chemical Abstracts, vol. 112, No. 10, 86672m (Mar. 1990), Bernstein P. A. et al. "Two-electron oxidation of cobalt phthalocyannes by thionyl chloride. Implications for lithium/thionyl chloride batteries." p. 626.
Cleavage of Alkyl 0-Hydroxphenyl Ethers, Robert G. Lange, Organic Chemicals Division, Nov. 27, 1961, pp. 2037-2039.
Chem. Ber., 2761 (1960), Walter Mayer, et al.
Structural Models of Cortin Compounds in the Naphthalene Series, JOC 6, 852 (1941), Louis Long, et al.
Chem. Ber., 76B, 900 (1943), Richard Kuhn, et al.
Aihara Shin
Itoh Hisato
Oguchi Takahisa
Sugimoto Kenichi
Mitsui Toatsu Chemicals Incorporated
Shah Mukund J.
Sripada P. K.
Yamamoto Chemicals, Incorporated
LandOfFree
Halogenated phthalocyanine compound, method for preparing same does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Halogenated phthalocyanine compound, method for preparing same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Halogenated phthalocyanine compound, method for preparing same will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1266569