Photochromic naphthopyrans

Details Photochromic naphthopyrans Photochromic naphthopyrans

1999-12-17

2002-03-05

Solola, T. A. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S150000, C544S375000, C546S196000, C548S311400, C548S364400, C548S440000, C548S454000, C548S525000, C549S043000, C549S060000, C549S331000, C549S389000

Reexamination Certificate

active

06353102

ABSTRACT:

DESCRIPTION OF THE INVENTION
The present invention relates to certain novel naphthopyran compounds. More particularly, this invention relates to novel photochromic naphthopyran compounds. Still more particularly, this invention relates to compositions and articles containing such novel naphthopyran compounds. When exposed to light radiation containing ultraviolet rays, such as the ultraviolet radiation in sunlight or the light of a mercury lamp, many photochromic compounds exhibit a reversible change in color. When the ultraviolet radiation is discontinued, such a photochromic compound will return to its original color or colorless state.
Various classes of photochromic compounds have been synthesized and suggested for use in applications in which a sunlight-induced reversible color change or darkening is desired. U.S. Pat. No. 5,458,814 discloses 2H-naphtho[1,2-b]pyrans, which are substituted at the 5- and 6-positions of the naphthopyran ring, that possess a reasonable rate of fade as well as high colorability. Said compounds exhibit activated colors ranging from yellow to red/purple.
International Patent Application Publication No. WO 98/42693 describes naphtho[1,2-b]pyrans having amino functional groups as substituents at the 7- or 9-positions of the naphthopyran ring. These compounds are disclosed as exhibiting a brown or brown/red activated color. A brown/red color is the perception by the eye of a major visible absorption in the 420-500 nm range coupled with a minor visible absorption in the 520-560 nm range.
While the activated form of a typical organic photochromic molecule absorbs in the visible region over a relatively narrow range (Van Gemert and Kish, PPG Technology Journal, Vol. 5, pg. 53-61, 1999), naphthopyrans having two absorption bands, are known.
International Patent Application Publication No. WO 98/04937 describes naphtho[1,2-b]pyrans having alkoxy groups as substituents at the 7- and 9-positions of the naphthopyran ring. The activated forms of these compounds exhibit two intense absorption bands in the visible light range.
The present invention relates to novel substituted 2H-naphtho[1,2-b]pyran compounds having substituents at the 2-position of the pyran ring, certain substituents at the 5 and 6 positions of the naphtho portion and optional substituents at the 7, 8, 9 and 10 positions of the naphtho portion of the compound. The activated forms of these compounds have unexpectedly been found to demonstrate two intense spectral bands in the visible spectrum. The absorption of one band, e.g., band “A”, occurs in the 400-500 nm region, while the absorption of the second band, e.g., band “B”, occurs in the 480-620 nm region. These compounds exhibit an apparent blended orange/brown to gray activated color. The use of certain individual compounds of the present invention eliminates the need for combining two or more compounds to obtain neutral colors such as gray or brown.
DETAILED DESCRIPTION OF THE INVENTION
In recent years, photochromic plastic materials, particularly plastic materials for optical applications, have been the subject of considerable attention. In particular, photochromic ophthalmic plastic lenses have been investigated because of the weight advantage they offer, vis-a-vis, glass lenses. Moreover, photochromic transparencies for vehicles, such as cars and airplanes, have been of interest because of the potential safety features that such transparencies offer.
In accordance with the present invention, it has now been discovered that certain novel 2H-naphtho[1,2-b]pyrans, having two absorption bands in the activated (colored) state, an acceptable fade rate, high activated intensity and a high coloration rate may be prepared. These compounds may be described as 2H-naphtho[1,2-b]pyrans having substituents at the 2 position of the pyran ring, certain substituents at the 5 and 6 positions and optional substituents at the 7, 8, 9 and 10 positions of the naphtho portion of the compound. These compounds may be represented by the following graphic formula I in which the letters a through n on the outside of the ring structure represent the sides or faces of the naphthopyran ring, and the numbers on the inside of the ring structure represent the numbers of the ring carbon atoms or ring positions of the naphthopyran. In the definition of the substituents shown in the following graphic formula I, like symbols have the same meaning, unless stated otherwise.
In graphic formula I, R
1
may be selected from hydroxy, C
1
-C
6
alkoxy, aryloxy, aryl(C
1
-C
6
)alkoxy, the unsubstituted, mono- or di-substituted aryl groups, phenyl or naphthyl, amino, mono(C
1
-C
6
)alkylamino, di(C
1
-C
6
)alkylamino, phenylamino, mono- or di-(C
1
-C
6
)alkyl substituted phenylamino, mono- or di-(C
1
-C
6
)alkoxy substituted phenylamino, diphenylamino, mono- or di-(C
1
-C
6
)alkyl substituted diphenylamino, mono- or di-(C
1
-C
6
)alkoxy substituted diphenylamino, morpholino, thiomorpholino, piperazino, piperidino, dicyclohexylamino, pyrrolidyl, or the group —OCH(R
4
)Z, said aryl substituents of R
1
being selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
3
-C
6
cycloalkyl, phenyl(C
1
-C
6
)alkyl, amino, mono(C
1
-C
6
)alkylamino, di(C
1
-C
6
)alkylamino, dicyclohexylamino, diphenylamino, piperidino, morpholino, pyrrolidyl, bromo, chloro, fluoro, phenyl and naphthyl; Z is —CN, —CF
3
, chloro, fluoro or —C(O)R
8
; R
4
is hydrogen or C
1
-C
6
alkyl; and R
8
is hydrogen, C
1
-C
6
alkyl or C
1
-C
6
alkoxy.
Preferably, R
1
is selected from hydroxy, C
1
-C
4
alkoxy, the unsubstituted, mono- or di-substituted aryl groups, phenyl or naphthyl, amino, mono(C
1
-C
4
)alkylamino, di(C
1
-C
4
)alkylamino, phenylamino, mono- or di-(C
1
-C
4
)alkyl substituted phenylamino, mono- or di-(C
1
-C
4
)alkoxy substituted phenylamino, diphenylamino, mono- or di-(C
1
-C
4
)alkyl substituted diphenylamino, mono- or di-(C
1
-C
4
)alkoxy substituted diphenylamino, morpholino, piperidino, dicyclohexylamino, pyrrolidyl, or the group —OCH(R
4
)Z, said aryl substituents being selected from the group consisting of C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
3
-C
5
cycloalkyl, phenyl(C
1
-C
4
)alkyl, amino, mono(C
1
-C
4
)alkylamino, di(C
1
-C
4
)alkylamino, dicyclohexylamino, diphenylamino, piperidino, morpholino, pyrrolidyl, bromo, chloro, fluoro, phenyl and naphthyl; Z is —CN, chloro, fluoro or —C(O)R
8
; R
4
is hydrogen or C
1
-C
4
alkyl; and R
8
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy.
More preferably, R
1
is selected from hydroxy, C
1
-C
3
alkoxy, phenyl, mono- or di-substituted phenyl, amino, mono(C
1
-C
3
)alkylamino, di(C
1
-C
3
)alkylamino, morpholino, piperidino, pyrrolidyl, or the group —OCH(R
4
)Z, said phenyl substituents being selected from the group consisting of C
1
-C
3
alkyl, C
1
-C
3
alkoxy, phenyl(C
1
-C
3
)alkyl, amino, mono(C
1
-C
3
)alkylamino, di(C
1
-C
3
)alkylamino, piperidino, morpholino, pyrrolidyl, bromo, chloro, fluoro, phenyl and naphthyl; Z is chloro, fluoro or —C(O)R
8
; R
4
is hydrogen or C
1
-C
3
alkyl; and R
8
is hydrogen, C
1
-C
3
alkyl or C
1
-C
3
alkoxy.
R
2
in graphic formula I, may be the group, —C(O)W, wherein: W is hydrogen, hydroxy, C
1
-C
6
alkyl, the unsubstituted, mono- or di-substituted aryl groups, phenyl or naphthyl, the group, —OCH(R
4
)Z, —OR
5
, or —N(R
6
) (R
7
) or an unsubstituted, mono-substituted or di-substituted aromatic and/or non-aromatic heterocyclic ring selected from the group consisting of 1-indolinyl, morpholino, thiomorpholino, piperidino, 1-pyrrolidyl, 1-imidazolidyl, 2-imidazolin-1-yl, pyrazolidyl, pyrazolinyl and 1-piperazinyl; R
5
is C
1
-C
6
alkyl, allyl, phenyl(C
1
-C
3
)alkyl, mono(C
1
-C
6
)alkyl substituted phenyl(C
1
-C
3
)alkyl, mono(C
1
-C
6
)alkoxy substituted phenyl(C
1
-C
3
)alkyl, (C
1
-C
6
)alkoxy(C
2
-C
4
)alkyl, C
1
-C
6
haloalkyl, or the unsubstituted, mono- or di-substituted aryl groups, phenyl or naphthyl, said halo substituent being chloro or fluoro; and R
6
and R
7
are each selected from the group consistin

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