Benzoselenazolino-vinylspiropyran compound

Chemistry: fischer-tropsch processes; or purification or recover – Group viii metal containing catalyst utilized for the... – Iron containing catalyst

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C07D29312

Patent

active

052369587

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a benzoselenazolino-vinylspiropyran compound and polymers prepared from the compound.


PRIOR ART

Spiropyran derivatives are best known as typical organic compounds reversibly becoming colored or colorless depending on the light or heat energy condition. Specific examples of these derivatives and physical characteristics thereof are summarized, for example, in G. H. Brown: Photochromism (John Wiley & Sons, Inc., 1971).
For practical use as recording media, however, the so-far known spiropyran derivatives have drawbacks; for instance (1) colored species (or uncolored species), in solutions as well as in macromolecular binders, are lacking in light or heat stability and therefore immediately return to the colorless state (or colored state); (2) in the course of repeated color change (recording and erasing) under the influence of light and heat, the spiropyran derivatives are decomposed or degraded due to side reactions arising from the light irradiation, hence can not have satisfactory repetition cycles; (3) while, for use as photochromic media, the spiropyran derivatives are generally dispersed in an aralkyl group; R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group having 1 to 5 carbon atoms, a halogen atom, a cyano group, a trichloromethyl group, a trifluoromethyl group or a nitro group; R.sup.6 and R.sup.7 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group, an aralkyl group, a halogen atom, a cyano group or a nitro group; and X is an oxygen atom or a sulfur atom.
The compound represented by the formula (Ia) of the present invention is a novel compound which has never been heretofore disclosed in the literature and which can be expected to be utilizable in such fields as high-density photo-recording materials, optical filters, image-forming materials, photosensitive materials, nonlinear optical devices, and conversion of light energy to mechanical energy. For example, a polymer which is obtained by dissolving the compound in an appropriate macromolecular compound or copolymerizing the compound with an optional polymerizable compound is uniformly applied to a substrate such as a glass material, whereby optical disk and like high-density recording media can be produced by a conventional procedure.
A macromolecular spiropyran compound which has a desired structure and a desired spiropyran group content can be formed by homopolymerizing the compound represented by the formula (Ia) or by copolymerizing this compound with an appropriate polymerizable compound.
In view of the above, the present invention also provides a polymer of a benzoselenazolino-vinylspiropyran compound which is characterized by comprising (a) 0.001 to 100 mole % of the structural unit represented by the formula ##STR2## wherein R.sup.1 is an alkyl group having 1 to 20 carbon atoms or an aralkyl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group having 1 to 5 carbon atoms, a halogen atom, a cyano group, a trichloromethyl group, a trifluoromethyl group or a nitro group; R.sup.6 and R.sup.7 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group, an aralkyl group, a halogen atom, a cyano group or a nitro group; and X is an oxygen atom or a sulfur atom; and
(b) 0 to 99.999 mole % of the structural unit represented by the formula ##STR3## wherein Y is a hydrogen atom or a methyl group; and Z is a carboxyl group, an alkoxycarbonyl group, a cyano group, a carbamoyl group, an N,N-dimethylcarbamoyl group, an acetoxy group, a phenyl group or a methylphenyl group.
The compound of the formula (Ia) of the present invention is designed for obviating the aforemetioned drawbacks of the prior

REFERENCES:
patent: 4197124 (1980-04-01), Ikeda

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