Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1987-08-19
1988-09-20
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C07D49810
Patent
active
047727004
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
The present invention relates to a novel spiropiperidine-naphthoxazine compound. More particularly, it relates to a spiropiperidine-naphthoxazine compound having photochromic characteristics giving an excellent repeatability.
2. Background Art
By photochromism is meant a reversible phenomenon wherein the color of a compound is changed under irradiation with light containing ultraviolet rays, such as sunlight or the light of a mercury lamp, and when the compound is placed in the dark place and irradiation is stopped, the original color is restored. A compound exhibiting this phenomenon is called "a photochromic compound".
Many photochromic compounds have been heretofore synthesized but very few compounds are practically used on an industrial scale. This is because, when photochromic compounds are used several times repeatedly, the photochromic compounds are deteriorated and they fail to show a photochromism or the color quality is degraded. Because of this defect, although many photochromic compounds and their applications have been proposed in patent publications and the other literatures, only a limited number of compounds are practically used.
Recently, a photochromic compound having a relatively good adaptability to repeated use has been proposed, for example, by H. G. Heller et al in J. Chem. Soc. Perkin Trans. I, 1981, page 202. However, this photochromic compound still has an insufficient adaptability to repeated use.
DISCLOSURE OF THE INVENTION
We carried out research with a view to overcoming the above-mentioned problems of the conventional technique and improving the adaptability to repeated use of a photochromic compound. As the result, we found chromic compounds having an excellent adaptability to repeated used and have now completed the present invention based on this finding.
More specifically, in accordance with the present invention, there is provided a spiropiperidine-naphthoxazine compound represented by the following general formula (I): ##STR2## wherein (a) R.sub.1 represents a linear or branched alkyl group having 1 to 18 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, which may be substituted, an alkenyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms, which may be substituted, (b) R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, and R.sub.9 represent independently a group R.sub.1 defined above, a hydrogen atom or an alicyclic ring having 5 to 10 carbon atoms or a norbonyl or adamantyl group, which is bonded between groups present on one skeleton carbon atom or between groups present on adjacent skeleton carbon atoms (at the ortho-position), (c) R.sub.10 represents a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, an aralkyl group having 7 to 15 carbon atoms, which may be substituted, or an alkenyl group having 1 to 10 carbon atoms, and (d) R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, and R.sub.16 represent independently a hydrogen atom, a linear or branched alkyl group having 1 to 9 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group or a cyano group.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 shows an NMR spectrum of the compound prepared in Example 1;
FIG. 2 shows an IR spectrum of this compound;
FIG. 3 shows a visible ray absorption spectrum of this compound; and,
FIG. 4 is a diagram illustrating the adaptability of the compound (a) prepared in Example 1 to repeated use, in contrast to that of the compounds (b) and (c) obtained in Comparative Examples 1 and 2.
BEST MODE FOR CARRYING OUT THE INVENTION
The spiropiperidine-naphthoxazine compound of the present invention is a novel compound not disclosed in any literature reference. Preferred examples are compounds of the above-mentioned general formula (I) in which (a) R.sub.1 represents a linear or branched alkyl group having 1 to 4 carbon atoms, (b) R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 represent independently a hydrogen atom, a methyl group or an et
REFERENCES:
patent: 3562172 (1971-02-01), Ono et al.
patent: 4342668 (1982-08-01), Hovey et al.
patent: 4636561 (1987-01-01), Hosoda
patent: 4699473 (1987-10-01), Chu
Kawauchi Susumu
Saeda Shigeru
Yoshida Haruo
Raymond Richard L.
Showa Denko Kabushiki Kaisha
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