Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-11-08
1998-01-13
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D51710
Patent
active
057081816
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/00396 filed Mar. 10, 1995.
TECHNICAL FIELD
The present invention relates to a spiropyran compound showing negative photochromism.
BACKGROUND ART
Photochromism is a phenomenon wherein a material reversibly changes in absorption spectrum by light irradiation. Spiropyran derivatives are typical and best known organic compounds showing such a phenomenon. For specific examples and physical properties of said derivatives, G. H. Brown: Photochromism (John Wiley & Sons, Inc. 1971) can be consulted, for example. Most of said derivatives show normal photochromism, i.e., a characteristic of being colorless at the normal state but colored by ultraviolet irradiation.
On the other hand, benzoselenazoline-type spiropyran compounds are known as typical compounds showing negative photochromism. Thus, said compounds have a color at the normal state, lose their color by irradiation with visible light and revert to the original colored state by subsequent ultraviolet irradiation or heating. Said compounds are disclosed, for example, in Japanese Unexamined Patent Publications No. 78685/1990 and No. 289587/1990, Published Searched Application No. 813072/1991 and the like. However, all of the known compounds have the maximum absorption wavelength at 500 to 600 nm, and no compounds have been found which are highly sensitive to visible light or a laser beam in the wavelength region of 400 to 500 nm.
Recently, an attempt has been made to use a compound showing photochromism (hereinafter referred to as "photochromic compound") as optical materials such as optical information recording media, optical filters and the like. However, as mentioned above, the conventionally known photochromic compounds have the maximum absorption wavelength at 500 nm or more. In view of increasing demands for recording in higher density and developing second harmonic generation materials (hereinafter referred to as "SHG materials") which shorten or convert the wavelength of a semiconductor laser beam, photochromic compounds which are sensitive (or responsive) to light of shorter wavelengths have been demanded.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a compound which has the maximum absorption wavelength at 400 to 500 nm and is highly sensitive to light in said wavelength region.
The compound of the present invention is a novel compound which has not been disclosed in any literature, the compound being a salt of a benzoselenazoline-type spiropyran compound of the formula (1) (hereinafter briefly referred to as "spiropyran compound (1)) and an acidic compound. ##STR2## wherein R.sup.1 means a C.sub.1 to C.sub.20 alkyl group, an aralkyl group, a hydroxyethyl group, acryloxyethyl group or a methacryloxyethyl group, R.sup.2 and R.sup.4 are the same or different and each mean a hydrogen atom, a C.sub.1 to C.sub.6 alkyl group, an aryl group, an aralkyl group, a C.sub.1 to C.sub.5 alkoxy group, a halogen atom, a cyano group, a trichloromethyl group, a trifluoromethyl group or a nitro group, R.sup.3 and R.sup.5 are the same or different and each mean a hydrogen atom, a C.sub.1 to C.sub.6 alkyl group, an aryl group, an aralkyl group, a C.sub.1 to C.sub.5 alkoxy group, a halogen atom, a cyano group, a trichloromethyl group, a trifluoromethyl group, a nitro group, an amino group, a dimethylamino group or a diethylamino group, R.sup.6 and R.sup.7 may be the same or different and each mean a hydrogen atom, a C.sub.1 to C.sub.6 alkyl group, an aryl group, an aralkyl group, a halogen atom, a cyano group or a nitro group, R.sup.8 means a hydrogen atom, a vinyl group, a group --CH.sub.2 OR.sup.9 or a group --CH.sub.2 OCOC(R.sup.10).dbd.CH.sub.2 (wherein R.sup.9 means a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group and R.sup.10 means a hydrogen atom or a methyl group), and X means an oxygen atom or a sulfur atom.
In formula (1), the C.sub.1 to C.sub.20 alkyl group represented by R.sup.1 is a straight- or branched-chain C.sub.1 to C.sub.20 alkyl group, and specific examples include methyl
Hama Hiroshi
Nakano Shinji
Gerstl Robert
Otsuka Kagaku Kabushiki Kaisha
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