Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1997-01-29
1999-08-10
Hoke, Veronica P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
252586, 351163, 359885, 544 71, C08K 534, G02C 710, C07D26500
Patent
active
059360160
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The invention relates to novel photochromic compounds of and containing a 7',8'-fused benzene ring on the benzoxazine nucleus, and to their use in the ophthalmic optics field, in particular in and/or on ophthalmic lenses.
BACKGROUND OF THE INVENTION
Photochromism is a phenomenon which has been known for many years. A compound is said to be photochromic when, after irradiation with a beam of light, certain wavelengths of which are in the ultraviolet region, this compound changes color and returns to its original color as soon as the irradiation ceases.
There are many applications of this phenomenon, but one of the more particularly advantageous known applications relates to the ophthalmic optics field.
Such compounds can be used in the manufacture of lenses or spectacle lens glasses for the purpose of screening light radiation as a function of its intensity.
The incorporation of photochromic compounds into an organic material constituting an ophthalmic lens makes it possible to obtain a lens glass whose weight is considerably reduced when compared with conventional lenses made of inorganic glass, which contain silver halides as photochromic agents. Their incorporation into organic materials has always posed technical difficulties.
However, any compound with photochromic properties cannot necessarily be used in the ophthalmic optics field. The reason for this is that the photochromic compound must satisfy a certain number of criteria, including, inter alia: photochromic compound to have an intense color after isomerization; suitable, alone or in combination with other photochromic compounds to be used in ophthalmic glasses or lenses; range, and in particular preferably between 0 and 40.degree. C.
The known and currently used organic photochromic compounds generally have a decreasing photochromism when the temperature increases, such that the photochromism is particularly pronounced at temperatures close to 0.degree. C., whereas it is much weaker, or even nonexistent, at temperatures of about 40.degree. C., these being temperatures which lens glasses may reach, in particular during exposure to the sun.
Another problem encountered for the photochromic compounds of the prior art is their lifetime. Indeed, for certain products of the prior art, a relatively short lifetime is observed. The reason for this is that after a certain number of coloration and decoloration cycles, the compound no longer has reversible photochromic properties.
The photochromic properties of spiroxazines have been described by R. E. Fox in the document Final Report of Contact AF 41, A.D. 440226 1961. 657.
Compounds of the spiro (indoline-naphthoxazine) type have been synthesized and described in particular in the article by N. Y. C. Chu "Photochromism: Molecules and Systems" Ed. H. Durr, H. Bovas Laurent, Elsevier, Amsterdam 1990, ch. 24, as well as compounds of the spiro(indoline-quinazolinoxazine) or spiro(indoline-benzothiazoloxazine) type in U.S. Pat. Nos. 5,139,707 and 5,114,621 (R. Guglielmetti, P. Tardieu) granted in the name of the company Essilor. also been synthesized and described in patent application EP-0,245,020.
Japanese patent application JP 3,251,587 moreover discloses photochromic compounds of the indolinospiropyridobenzoxazine type bearing, in the 6' position of the benzoxazine nucleus, CN, CF.sub.3 or alkoxycarbonyl groups, and the indoline nitrogen of which is substituted with alkoxycarbonylalkyl groups.
These compounds are photochromic at temperatures of about from 30 to 40.degree. C.
These compounds, in their open form, have an absorption spectrum in the visible region containing an absorption maximum at a wavelength .lambda..sub.max ranging from 600 to 617 nm.
It is desirable to obtain compounds whose absorption spectrum in the visible region, for their open form, contains an absorption maximum at wavelengths higher than those of the compounds of patent application JP 3,251,587.
Indeed, shifting of the .lambda..sub.max value to higher values leads to photochromic compounds of color approa
REFERENCES:
patent: 3578602 (1971-05-01), Ono et al.
patent: 4286957 (1981-09-01), Le Naour-Sene
patent: 4342668 (1982-08-01), Hovey et al.
patent: 4880667 (1989-11-01), Welch
patent: 4931220 (1990-06-01), Haynes et al.
patent: 5000878 (1991-03-01), Chu
patent: 5114621 (1992-09-01), Guglielmetti
patent: 5139707 (1992-08-01), Guglielmetti
patent: 5446151 (1995-08-01), Rickwood et al.
Guglielmetti Robert
Lareginie Pierre
Lokshin Vladimir
Samat Andre
Zaballos Garcia Elena
Essilor International "Compagnie Generale d'Optique"
Hoke Veronica P.
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