Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1999-01-29
2000-10-24
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540580, 351163, 252586, C07D49810, G03C 1685
Patent
active
061369683
DESCRIPTION:
BRIEF SUMMARY
This application is a International 371 of PCT Application No. PCT/FR97/01196 filed Jul. 3, 1997.
The invention relates to novel photochromic compounds, more particularly photochromic compounds of the homoazaadamantane spirooxazine family, to their use in the field of ophthalmic optics, in particular in and/or on ophthalmic lenses, and to lenses for optical equipment.
The phenomenon of photochromism has been known for many years. A compound is said to be photochromic when, after irradiation with a light beam certain wavelengths of which are situated in the ultraviolet range, this compound changes color and returns to its original color once the irradiation is stopped.
This phenomenon has many applications, but one of the more particularly advantageous known applications relates to the field of ophthalmic optics.
Such compounds may be used in the production of lenses or glass for spectacles in order to filter light radiations depending on their intensity.
By incorporating photochromic compounds into an organic material constituting an ophthalmic lens, it is possible to obtain a glass of considerably reduced weight relative to conventional lenses made of inorganic glass which contain silver halides as photochromic agent. Their incorporation into organic materials has always posed technical difficulties.
However, not all compounds with photochromic properties are necessarily usable in the field of ophthalmic optics. Indeed, the photochromic compound must fulfill a certain number of criteria, some of which are: photochromic compound to show an intense color after isomerization; compound capable of being used, alone or in combination with other photochromic compounds, in ophthalmic glass or lenses; particular preferably between 0 and 40.degree. C.
The organic photochromic compounds currently known and used generally show decreasing photochromism as the temperature rises, 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 the order of 40.degree. C., which are temperatures which the glass may reach especially on exposure to the sun.
Another problem encountered by the photochromic compounds of the state of the art is their lifetime. Indeed, for certain products of the state of the art, a relatively short lifetime is observed. In effect, after a certain number of coloration and decoloration cycles, the photochromic compound undergoes chemical degradation and no longer displays reversible photochromic properties.
Document EP-A-0,338,660 describes photochromic compounds of the spiro[3H-1,4-oxazine] family comprising a piperidine type ring grafted onto the spiran carbon. These compounds have satisfactory photochromic characteristics with, in particular a hypsochromic shift of the absorption wavelength in the visible range compared with the standard spiro[indolinenaphthoxazine] reference series. On the other hand, the synthesis of compounds from document EP-A-033,660 proves to be difficult, in particular as regards the piperidine precursor.
It would be desirable to prepare photochromic compounds having higher spectrokinetic constants and consequently better photochromic properties, and which are easy to synthesize.
The Applicant Company has discovered a novel family of spirooxazines which show particularly advantageous photochromic properties. Indeed, the compounds in accordance with the invention show strong colorability, especially in the pink or gray/green range, which is particularly useful for ophthalmic optics, these compounds therefore capable of being used with photochromic compounds giving a yellow or red color such as chromenes with a view to obtaining a natural final coloration on exposure to light.
Furthermore, the compounds in accordance with the invention have no coloration, or very little coloration, in the initial state and show rapid coloration and decoloration kinetics across a very broad temperature range, between 0 and 40.degree. C. in particular.
Furthermore, the compounds in accordance wit
REFERENCES:
patent: 4913544 (1990-04-01), Rickwood et al.
patent: 5186867 (1993-02-01), Castaldi et al.
Chamontin Karine
Guglielmetti Robert
Lokshin Vladimir
Samat Andre
Mallak Frank P.
Shah Mukund J.
Sripada Pavanaram K
Transitions Optical Inc.
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