Compositions – Light transmission modifying compositions – Displaying color change
Patent
1998-01-28
2000-02-29
Tucker, Philip
Compositions
Light transmission modifying compositions
Displaying color change
544 71, 523106, 525 66, G02B 523, C07D26500
Patent
active
06030555&
DESCRIPTION:
BRIEF SUMMARY
The present invention concerns novel compounds of the spiroxazine type presenting, in particular, photochromic properties. It also concerns the photochromic compositions and ophthalmic articles (e.g., lenses) which contain spiroxazines.
The photochromic compounds are capable of changing color due to the influence of a poly- or monochromatic light (e.g., UV) and they are capable of recovering their initial color when the irradiation with light stops, or due to the influence of a poly- or monochromatic light which is different from the first light, or due to the influence of temperature and/or of a poly- or monochromatic light which is different from the first one.
These photochromic compounds are applied in various fields, for example, for the manufacture of ophthalmic lenses, contact lenses, some sunshades, filters, optics for cameras or photographic apparatus or other optical and observation devices, glass partitions, decorative objects, display elements or for the storage of information by optical inscription (coding).
In the filed of ophthalmic optics, and in particular in the field of eyeglasses, a photochromic lens, comprising one or more photochromic compounds, must present: sunlight, preferably), with, preferably, maintenance of the selected tint during the course of the coloration and the decoloration of the lens, range of 0-40.degree. C., sophisticated, and therefore expensive, corrective lenses.
These lens characteristics are in fact determined by the active photochromic compounds which, in addition, must be perfectly compatible with the organic or mineral support which constitutes the lens.
Moreover, it should be noted that the obtention of a gray or chestnut brown tint may require the use of at least two photochromes of different colors, that is, having distinct maximum absorption wavelengths in the visible range (.lambda..sub.max). This association thus imposes still other requirements on photochromic compounds. In particular, the kinetics of coloration and decoloration of the two or more associated active photochromic compounds must be essentially identical. The same applies to their stability over time and, also, to their compatibility with a plastic or mineral support.
Among the numerous photochromic compounds described in the prior art, one can cite the indolinospironaphtoxazines described in U.S. Pat. Nos. 3,578,602; 3,562,172; 4,215,010; European Patent Nos. 0,171,909; 0,313,941; French Patent No. 2,647,789 and European Patent No. 0,600,669: ##STR2##
The group R.sub.1 of these molecules represent straight or branched alkyls, alkylaryls or alicyclics. These compounds are considered to meet the specifications defined above.
In fact, while these compounds have indeed one or more of the basic properties sought, such as a high transmission in darkness, a high colorability when exposed to sun radiation, absorption in the blue or violet (570-630 nm), a rapid kinetics of coloration and decoloration, all the compounds described to this day do not have the complete combination of the wanted properties which is required for the production of satisfactory articles which can be manufactured industrially.
Whereas the prior art teach how to modify the absorption band by the addition of substituents to the different positions of the rings and, also, teach how to modify the kinetics of decoloration, in contrast, it does not teach how to increase the colorability of these molecules without increasing the residual coloration in the inactivated state and, above all, on how to make them photochemically stable so as to allow their use on an industrial scale. Indeed, without a high stability, these expensive molecules, introduced into a sophisticated lens, cannot be used.
It is the merit of the applicant to have found, unexpectedly, that the presence of polycyclic groups, preferably bicycloalkyl groups, allowed a solution of the problem of the stability, the residual coloration and the colorability, which are essential for the above-mentioned applications.
The originality of the invention resides in the surpri
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Corning Incorporated
Nwaneri Angela N.
Rogalskyj Peter
Tucker Philip
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