Spiropyran compounds and optically active spiropyran compounds a

Details Spiropyran compounds and optically active spiropyran compounds a Spiropyran compounds and optically active spiropyran compounds a

1994-11-14

1996-05-28

Schofer, Joseph L.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526263, 526266, 526284, 526288, 548409, C08F12606, C08F12400, C08F12800, C07D48710, C07D491107, C07D49510

Patent

active

055212697

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel spiropyran compounds and optically active spiropyran compounds and their use. The compound of the present invention is expected for use in the fields of optical materials such as high-density optical recording materials, optical filters, image forming materials, non-linear optical devices, writable high-density optical recording materials wherein non-destructive read-out has been accomplished, photosensitive materials, non-linear optical device and conversion of optical energy into dynamic energy.


BACKGROUND ART

Spiropyran compounds are most well-known as typical organic compounds which reversibly colors or decolorizes upon exposure to the energy of light or heat. Examples and properties of these derivatives are collectively described, for example, in G. H. Brown, "Photochromism" (John Wiley & Sons, Inc., 1971). Spiropyran compounds have an asymmetric center on a spirocarbon. However, all conventional spiropyran compounds are perfect racemic modifications having an optical purity of 0%, and optically active spiropyran compounds which exhibit specific properties of optical active substances such as optical rotation have never been obtained.
The present inventors have studied intensively in order to solve the above problem of the prior art. That is, an object of the present invention is to provide spiropyran compounds and optically active spiropyran compounds and their use.


DISCLOSURE OF THE INVENTION

The present invention provides a spiropyran compound represented by the formula (1): ##STR2## wherein R.sup.1 is alkyl group having 1 to 20 carbon atoms, aralkyl group, hydroxyethyl group, methacryloxymethyl group or methacryloxyethyl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom, alkyl group having 1 to 6 carbon atoms, aryl group, aralkyl group, alkoxy group having 1 to 5 carbon atoms, hydroxymethyl group, carboxyl group, halogen atom, amino group, cyano group, trichloromethyl group, trifluoromethyl group or nitro group; R.sup.6 and R.sup.7 are the same or different and are each hydrogen atom, alkyl group having 1 to 6 carbon atoms, aryl group, aralkyl group, halogen atom, cyano group or nitro group; R.sup.8 is alkyl group having 1 to 6 carbon atoms, hydroxymethyl group, carboxyl group, methoxycarbonyl group, methacryloxymethyl group or vinyl group; at least one of R.sup.1 to R.sup.8 is substituted with a substituent having properties as a reagent for optical resolution; and X is oxygen atom or sulfur atom.
The present invention also provides an optically active spiropyran compound wherein an asymmetric center is introduced on a spirocarbon, which is represented by the formula (2): ##STR3## wherein R.sup.1 to R.sup.8 and X are the same as above.
Further, the present invention provides an optical functional material containing the spiropyran compound of the formula (1) or (2).
The spiropyran compound of the above formula (1) and the optically active spiropyran compound of the above formula (2) are compounds which are not described in literatures.
In the present specification, examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, hexyl group, nonyl group, dodecyl group, heptadecyl group, eicosyl group and the like. Examples of the aryl group include phenyl group, naphthyl group and the like. These groups may be substituted with substituents such as alkyl group having about 1 to 6 carbon atoms, alkoxy group having about 1 to 5 carbon atoms, halogen atom and the like. Examples of the aralkyl group include benzyl group, phenylethyl group, naphthylmethyl group and the like. The aromatic ring of these groups may be substituted with substituents such as alkyl group having about 1 to 6 carbon atoms, alkoxy group having about 1 to 5 carbon atoms, halogen atom and the like. Examples of the alkoxy group having 1 to 5 carbon atoms include methoxy group, ethoxy group, propoxy group, pentoxy group and the like. Examples of the halogen atom include fl

REFERENCES:
patent: 5241027 (1993-08-01), Miyashita

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