Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1997-04-04
1998-11-03
Grumbling, Matthew V.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C07D26500, C07D29500
Patent
active
058310908
DESCRIPTION:
BRIEF SUMMARY
This application claims benefit of PCT/FR94/00918, filed Jul. 22, 1994, under 35 U.S.C. .sctn.371.
The present invention relates to a novel process for the preparation of type.
Photochromism is a well-known reversible phenomenon which is illustrated, for example, by a compound which changes color when it is exposed to light radiation some of which is in the UV region, in particular solar radiation, and which resumes its initial color when the exposure to light is interrupted.
Such compounds are used, for example, in the manufacture of lenses for protective sunglasses or in other applications which involve the need to vary the transparency of an article as a function of the surrounding light intensity. They may be applied to a transparent support or incorporated into a transparent polymerized organic material in combination with a very wide variety of polymer compositions.
A certain number of organic photochromic compounds containing an indolinospirooxazine group in their formula have already been proposed for such applications, particularly in the field of ophthalmic lenses.
Thus, U.S. Pat. Nos. 3,562,172 and 3,578,602 have disclosed the photochromic effect of certain compounds belonging to the family of indolinospironaphthoxazines, whereas U.S. Pat. No. 4,215,010 describes indolinospironaphthoxazines in which the naphthalene ring system is substituted with methoxy or ethoxy groups or a halogen atom. Analogous photochromic compounds containing a pyridobenzene ring system instead of the naphthalene ring system of the above compounds are described in U.S. Pat. No. 4,720,547, as well as in international application WO 87/00524.
However, the compounds described in this prior art do not fully satisfy all of the qualities expected thereof. If we consider more particularly the context of the application to sun-protective lenses, the photochromic material obtained, either from a solution of the photochromic compound or by incorporation of the latter into an organic polymer, must have a certain number of properties regarding the photochromic effect, in addition to its natural transparency and its compatibility with the materials commonly used for such lenses.
In particular: must appear rapidly, preferably within a period of about a second, and its disappearance when the irradiation ceases must be just as rapid. photochromism. Thus, the compound must be able to tolerate, within the material, a large number of coloration-decoloration cycles, throughout a period of use which may be several years. compound, and the absorption spectrum of the irradiated material must cover the entire visible spectrum as much as possible. containing the compound, and it should be exhibited over a wide temperature range, both at variable ambient temperatures and when it is heated under irradiation. aesthetic concerns, by preserving a pleasant view of the environment for the wearer of ophthalmic spectacles or lenses made of such materials. From this point of view, blue colors, to which the compounds of the abovementioned prior art generally lead, should be avoided and green should be favored.
In the aim of satisfying these conditions, French patent applications 2,647,789 and 2,647,790 and European patent application EP-0,245,020 have already proposed photochromic compounds corresponding to the annelated the benzoxazine part is ortho-fused to an aromatic or non-aromatic heterocyclic ring.
These compounds are obtained by a process including a condensation of a free Fischer base of the 2-alkylideneindoline type with an annelated 1-nitroso-2-phenol derivative.
According to a variant of this process, the Fischer base can also be prepared in situ from a corresponding indoleninium salt in the presence of a base such as piperidine or triethylamine.
The Applicant has discovered, unexpectedly, a novel process for the makes it possible to obtain higher yields of final product than in the prior processes defined above for the same final product.
The process of the invention also makes it possible to work under milder conditions than in the processes o
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Chelepin Nikolai E.
Minkin Vladimir I.
Paltchkov Victor A.
Trofimova Nadezhda S.
Zoubkov Oleg A.
Essilor International (Compagnie Generale D'Optique)
Grumbling Matthew V.
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