Compositions – Light transmission modifying compositions – Displaying color change
Patent
1998-02-02
1999-12-21
Raymond, Richard L.
Compositions
Light transmission modifying compositions
Displaying color change
351163, 359241, 359242, 359674, 359885, 430340, C07D41302, C07D41304, C07D41314
Patent
active
060044861
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 covering their initial content, 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 the 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 photography apparatuses or other optical devices or observation devices, glass partitions, decorative objects, elements of displays or for the storage of information by optical inscription (encoding).
In the field 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., 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; European Patent No. 0,600,669: ##STR3##
The group R.sub.1 of these molecules represent linear 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 wanted basic properties, such as high transmission in darkness, high colorability when exposed to sun radiation, absorption in the blue or violet [spectrum] (570-630 nm), rapid kinetics of coloration and decoloration, all the compounds described to this day do not have the complete combination of the desired properties that are required for the production of satisfactory articles, which can be manufactured industrially.
Whereas the prior art teaches how to modify the absorption band by the addition of substituents to the different positions of the rings and also 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 an asymmetric monocyclic substituent group on the nitrogen atom of the indoline or portion of certain indolinospiroxazines allows the solution of the problem of the residual coloration and of the colorability, which is essential for the indicated applications.
The ori
REFERENCES:
patent: 5139707 (1992-08-01), Guglielmetti et al.
Tateoka et al., Chemical Abstracts, vol. 111, abstract 87504z, 1989.
Murayama et al., Chemical Abstracts, vol. 114, abstract 133085a, 1991.
Corning Incorporated
Nwaneri Angela N.
Raymond Richard L.
Rogalskyj Peter
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