Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-07-30
1999-09-14
Lambkin, Deborah C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548131, 548215, 548224, C07D31192, C07D27106, C07D26302, C07D26356
Patent
active
059525150
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to photochromic diaryl-2H-naphtopyrans.
STATE OF THE ART
Pyrans have been known as photochromic compounds for 25 years. One of the first descriptions of pyrans is in U.S. Pat. No. 3,567,605, in which the various benzo- and naphthopyrans including diphenyl-naphtopyrans are also described. However for years these compounds have remained uninteresting, because they only dye at very low temperatures (-40.degree. C.).
Only recently have pyrans become known that also dye photochromically at normal temperatures and thus seem suited for use in ophthalmic lenses. Reference is made, by way of example, to U.S. Pat. No. 5,066,818, WO 93/10112 or WO 92/09593.
However, these known pyrans still have drawbacks with regard to their longevity and/or migration properties as well as their photochromic properties.
In particular, the material specific varying migration of the individual pyran compounds leads to inadequate dyeing results in surface coloring if these pyran compounds are utilized in mixtures, which are needed to obtain a desired mixed tone, because each individual compound penetrates to a different depth into the to-be-dyed material depending on the specific migration velocity.
The result are, comparable to the procedures in chromatography, layers in which the different pyran compounds are found in above average concentrations.
Moreover, the relatively great migration velocity of the compounds known from the state of the art results in a short lifetime of the dyed plastic objects. The known dyestuffs migrate relatively quickly out of the dyed object to its surface and cause separation phenomena there.
DESCRIPTION OF THE INVENTION
The object of the present invention is to provide substances, which dye photochromically well at room temperature, lighten up quickly enough for ophthalmic lenses, possess sufficient longevity and due to their spatial structure have less tendency to migrate than the compounds known from the state of the art, and to describe the synthesis of these substances.
An invented solution to this object is set forth in claims 1 and 2.
Further improvements of the present invention are the subject matter of the dependent claims.
The subject matter of the present invention are therefore photochromic compounds having a diaryl-2H-naphthopyran-structure, which possesses an advantageous substitution at its aryl substituents.
On the one hand, this substitution of the aryl substituents comprises linking the naphthopyran-structure to the first starting compound described in claim 2 under a) by means of the invented process, with which `monomeric` diaryl-2H-naphthopyrans which possess one photochromically reacting center are produced.
On the other hand, the photochromic substance yielded by the described process possesses an especially advantageous substitution of the aryl substituents if the aryl substituent of the diaryl-2H-naphthopyran compound is linked via the starting compound described in claim 2 under a) to at least one other diaryl-2H-naphthopyran compound.
Dependent on the selection of the starting compound ##STR1## the photochromic substance possesses a link of at least two photochromic partial systems, which either are characterized by an electron-conducting bridge or by a bridge that interrupts electron delocalization.
An element of the present invention is that it was understood that a solution to the object can succeed in a very simple manner by substituting the aryl substituents of the diaryl-2H-naphthopyran compounds known from the state of the art in a suitable manner.
All the photochromic properties such as color, darkening and lightening up velocity, temperature dependency and longevity of the photochromic reaction are retained; at the same time the invented compounds show distinctly less tendency to migrate than the compounds known from the state of the art.
Moreover, various diaryl-2H-naphthopyrans can be linked in this way. This has the advantage that several dyestuffs of varying absorption possess identical ability to migrate in an e
REFERENCES:
patent: 5066818 (1991-11-01), Gemert et al.
patent: 5238981 (1993-08-01), Knowles
patent: 5340857 (1994-08-01), Van Gemert
patent: 5369158 (1994-11-01), Knowles
patent: 5458814 (1995-10-01), Kumar et al.
patent: 5578252 (1996-11-01), Van Gemert et al.
patent: 5623005 (1997-04-01), Rickwood et al.
Melzig Manfred
Zinner Herbert
Lambkin Deborah C.
Optische Werke G. Rodenstock
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