Compositions – Light transmission modifying compositions – Displaying color change
Patent
1999-05-21
2000-11-14
Wu, Shean C.
Compositions
Light transmission modifying compositions
Displaying color change
549382, 549389, 549362, 549 60, 549 58, 548454, 548525, 548526, 5462811, 5462827, 544148, 544150, G02B 523, C07D31192, C08K 515
Patent
active
061465542
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to photochromic compounds, specifically indeno-anellated naphthopyrane dyes with different substituents, to a method of producing same, their application as well as to a photochromic object comprising said photochromic naphthopyrane dyes.
Various dye classes have become known which change their colour reversibly when they are exposed to light of certain wavelengths, in particular sun light. This is due to the fact that supply of energy in the form of light causes these dye molecules to pass over to an excited stage which, when the energy supply is stopped, they leave again for returning into their initial state. These photochromic dyes include, for instance, the naphthopyranes which have been described already with different substituents in prior art.
PRIOR ART
Pyranes, particularly naphthopyranes and major ring systems derived therefrom are that class of photochromic compounds which is predominantly operated on at present. Even though the first patent application was filed for them as early as in 1966 (U.S. Pat. No. 3,567,605) it was possible in the nineties only to develop compounds which appeared to be suitable for the application in spectacle glasses or lenses. One usable class of pyrane compounds are, for instance, the 2,2-diaryl-2H-naphtho[1,2-b]pyranes which, in their excited form, show different hues such as yellow, orange or red-orange. The indeno-anellated naphtopyranes are of interest as another class of photochromic compounds which present an absorption in the range of longer wavelengths due to their larger ring system. It is the systems derived from the 2,2-diaryl-2H-naphtho[1,2-b]pyranes which are produced from the respective naphthopyrane systems by anellation on the f-side.
For instance, the documents WO 96/14596 or the U.S. Pat. No. 5,656,767 disclose indeno[2,1-f]naphtho[1,2-b]pyrane systems, compounds containing these photochromic dyes, as well as a method of producing these compounds. The naphthopyrane systems described in these prior art references are to be modified to the effect that they will achieve a more rapid brightening than the 2H-naphthopyranes so far known. As a solution to this problem only hydrogen and alkyl groups are described by way of example as radicals R at position 13.
The very extensive list of substituents at the aryl or hetero-aryl groups, which is claimed in WO 96/14596 for B and B', mentions piperidine, morpholine and pyrrole in addition to amino, mono- and di-(C.sub.1 -C.sub.6)-alkyl amino groups, with details missing:
The aforedescribed compounds can, however, form fulvenes which, in the case of alkyl groups carrying a-hydrogen, are produced with splitting off water. These destructive products of intense colour are formed, inter alia, in the course of the life test (xenon light). Moreover, these photochromic dyes with the substituents claimed in WO 96/14596 or U.S. Pat. No. 5,656,767 can cover only that part of the spectral range which contains the shorter wavelengths, with the colour impression being orange to blue/grey (cf. for instance the description in lines 24/25 on page 2 of WO 96/14596).
Furthermore, in the manufacturing process according to these prior art documents partly highly aggressive reaction conditions are employed, e.g. the materials are heated for one hour with concentrated phosphoric acid at temperatures between 160 and 220.degree. C. (cf. reaction (5): cyclisation from D to E). Consequently, substituents with more sensitive groups are not applicable because they would be oxidised or decomposed under such conditions. In the synthesising approach described in WO 96/14596 or U.S. Pat. No. 5,656,767, respectively, i.e. the closing of the 6-ring before the 5-ring, moreover certain compounds cannot at all be prepared or prepared only with difficulties.
Furthermore, the aforedescribed compounds entail disadvantages because the commercially available lenses containing prior art compounds have a negative effect for the wearer of the glasses because under certain conditions strong colour distortions occur. At very l
REFERENCES:
patent: 5645767 (1997-07-01), Gemert
patent: 5698141 (1997-12-01), Kumar
patent: 5955520 (1999-09-01), Heller et al.
patent: 5961892 (1999-10-01), Gemert et al.
Mann Claudia
Melzig Manfred
Weigand Udo
Optische Werke G. Rodenstock
Wu Shean C.
LandOfFree
Photochromic naphtopyrane colorants, method for the production a does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photochromic naphtopyrane colorants, method for the production a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photochromic naphtopyrane colorants, method for the production a will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2061985