Radiation imagery chemistry: process – composition – or product th – Dye image from radiation sensitive dye or dye former by dry... – Composition or product
Patent
1992-11-12
1994-02-22
Bowers, Jr., Charles L.
Radiation imagery chemistry: process, composition, or product th
Dye image from radiation sensitive dye or dye former by dry...
Composition or product
430962, 252586, 548402, 548409, G03C 1735, C07D20996
Patent
active
052885925
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a transition metal-spirobenzopyran complex, a process for producing the complex, and a photochromic material comprising the complex.
BACKGROUND ART
The organic compounds undergoing a reversible change of color on exposure to photic or thermal energy which are typical and best known are spiropyran derivatives and G. H. Brown: Photochromism (John Wiley & Sons, Inc., 1971), for one, can be consulted for a specific listing of such derivatives and their physical properties.
However, when an attempt is made to exploit the hitherto-known spiropyran derivatives commercially in recording materials, they are found to have serious disadvantages. Thus, because the meta-stable species (ring opened isomers) are lacking in thermal stability in solutions as well as in polymeric binders, they tend to promptly revert to the ground state or fade out so that the chromic response at a necessary level cannot be sustained for a sufficient duration.
It is an object of the present invention to provide a compound free from the above-mentioned disadvantages of the prior art spiropyran derivatives.
It is a further object of the present invention to provide a compound exhibiting stable photochromism.
DISCLOSURE OF THE INVENTION
The inventor of the present invention explored in earnest for a solution to the above problems and found that a certain transition metal-spirobenzopyran complex is able to solve the above problems. The present invention has been developed on the basis of the above finding. The present invention accordingly has achieved a successful fixation of the colored form of spiropyrans which have been acknowledged to be thermally labile.
The transition metal-spirobenzopyran complex of the present invention is a novel compound which has not been described in the literature. It is a transition metal-spirobenzopyran complex of the following general formula. ##STR2## wherein R.sup.1 means an alkyl group of 1 to 20 carbon atoms or an aralkyl group. R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different and each means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group of 1 to 5 carbon atoms, a halogen atom, a cyano group or a nitro group. R.sup.6 and R.sup.7 may be the same or different and each means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an aryl group, an aralkyl group, a halogen atom, a cyano group or a nitro group. R.sup.8 means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, a chloromethyl group, a methacryloxymethyl group or a vinyl group. Y means an oxygen atom or a sulfur atom. M means a chromium atom, a molybdenum atom or a tungsten atom.
The addition of metal salts to photochromic compounds, such as spiropyrans and spironaphthoxazines, in an attempt to stabilize less stable colored form is reported, inter alia, in J. Amer. Chem. Soc. 87, 4020 (1965), J. Chem. Soc. Chem. Commun., 1477 (1989), the Proceedings of the 58th Spring Meeting of The Chemical Society of Japan, 1874 (1989) and the Proceedings of the 59th Spring Meeting of the same Society, 1983 (1990). According to Akio Yamamoto: Yukikinzoku Kagaku--Kisoto-Ooyo [Organometallic Chemistry--Fundamentals and Applications] (Syokabo, 1982), the term "organometallic compound" means a compound in which at least one metal element or semi-metal (metalloid) element is bound to the carbon atom of an organic group. However, the prior art compounds represented by the species referred to above invariably involve bonding between a carbon compound and a metal atom through a hetero-atom (oxygen, nitrogen or the like) and these species are, by convention, not called organometallic compounds.
Thus, the complex of the present invention is an organometallic compound in the true sense of the term in that there exist six metal-carbon bonds between the indoline moiety of an indolinospirobenzopyran and a transition metal of the VIA group, and is a quite novel transition metal-spirobenzopyran complex.
The
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Bowers Jr. Charles L.
McPherson John A.
Otsuka Kagaku Kabushiki Kaisha
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