Photochromic naphthopyran compounds

Details Photochromic naphthopyran compounds Photochromic naphthopyran compounds

2002-06-10

2003-09-30

Ramsuer, Robert W. (Department: 1626)

Compositions

Light transmission modifying compositions

Displaying color change

C528S196000, C528S198000, C528S199000, C524S110000, C544S150000, C549S389000

Reexamination Certificate

active

06627121

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to certain novel photochromic naphthopyran compounds and to compositions and articles comprising them.
BACKGROUND OF THE INVENTION
Naphthopyran compounds are known to be capable of exhibiting a photochromic effect and have been found to be useful for imparting photochromic properties to a polymeric host material. Naphthopyrans and their use in photochromic lenses have been described for example, in U.S. Pat. No. 4,826,977. U.S. Pat. No. 5,066,818, U.S. Pat. No. 5,238,981, U.S. Pat. No. 5,520,853, U.S. Pat. No. 5,552,090, U.S. Pat. No. 552,091, U.S. Pat. No. 5,623,005, U.S. Pat. No. 5,658,501, U.S. Pat. No. 5,932,725, EP 401958 and WO 95/05371, and have been reviewed by Crano et al.,
Pure & Appl. Chem
. 68 (1996) pp.1395-1398, and by Van Gemert et al.,
Mol. Cryst. Liq. Cryst
. 297 (1997) pp.131-138.
Photochromic naphthopyrans give yellow to blue colors. In combination with other naphthopyrans or with other photochromes such as spirooxazines, they give neutral gray or brown colors. Incorporation of these compounds into a plastic lens or another plastic article provides the articles with desirable photochromic properties. High photoinduced optical density, together with a high speed of thermal decoloration in the dark, are among the most desirable combination of properties that provide eyes with good protection, from intensive sunlight and fast lens color clearing in areas shaded from the sun.
The present invention relates to novel photochromic naphthopyran compounds containing a phenyl alkyl substituent in the naphthalene moiety of the photochrome that have enhanced optical density of the photoinduced color and fast decoloration speed in the dark. None of the publications mentioned above describe the compounds of the present invention.
SUMMARY OF THE INVENTION
In accordance with the present invention, a photochromic naphthopyran compound of the formula I is provided:
wherein
R
1
through R
15
, which may be the same or different, are independently selected from the group consisting of hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, C
1
-C
4
alkylcarbonyloxy, benzoyloxy, C
3
-C
6
cycloalkyl, phenyl, and NR
16
R
17
, wherein R
16
and R
17
are each C
1
-C
4
alkyl or together with the N atom form a 5-12 membered monocyclic or polycyclic ring having, optionally, one or more further heteroatoms;
R is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy, and
(C
n
H
2n+1
)—C—(C
m
H
2m+1
) is a tert-alkylene group, wherein n and m are integers from 1 to 5.
The alkyl and alkoxy radicals according to the invention may be linear or branched and have 1-4, preferably 1-2, more preferably, 1 carbon atom, e.g. methyl and methoxy radicals. R
1
through R
15
may be halogen selected from chloro, bromo, iodo and, preferably, fluoro. When NR
16
R
17
denotes a ring, it may be a saturated, unsaturated or aromatic 5-12 membered mono—or polycyclic ring having optionally one or more heteroatoms selected from nitrogen, oxygen or sulfur, such as, for example, but not being limited to, pyrrolidine, pyrrroline, piperidine, pyridine, piperazine, pyrimidine, quinoline, morpholine, thiazoline, thiazole, oxazoline, oxazole, and the like, and is preferably a saturated 5-6 membered, more preferably a 6-membered, ring optionally containing an oxygen atom, e.g. piperidino and morpholino.
The present invention further provides synthetic methods for making the photochromic naphthopyran molecules of formula I.
The naphthopyran compounds of the present invention be used as additives to polymers employed on optical filters of variable optical density, including plastic lenses to provide light-sensitive darkening effects.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides photochromic naphthopyran compounds of formula I.
The photochromic naphthopyran of formula I may be prepared by reacting the appropriately substituted benzophenone with sodium acetylide in a suitable solvent. The substituted propargyl alcohol obtained in this reaction is then coupled by a modified Claisen rearrangement with the appropriately substituted 2-naphthol in the presence of a suitable acid catalyst under mild reaction conditions to give the desired naphthopyran of formula I.
The starting benzophenone may be prepared by Friedel-Crafts reaction in which the benzoylchloride derivative is reacted with a substituted benzene derivative. The substituted 2-naphthol is formed by alkylation of a molecule of &bgr;-naphthol by &agr;-methylstyrene.
In the naphthopyran compounds of formula I, R and R
1
through R
5
are preferably hydrogen; R
6
through R
15
are preferably hydrogen, methoxy, methyl, fluor, dimethylamino, piperidino or morpholino; n and m are preferably 1 such that the group >C(C
n
H
2n+1
)(C
m
H
2m+1
) is preferably tert-propylene (C(CH
3
)
2
). These functionalities can be synthesized by chemical reactions known in the art, once one understands the present invention.
The photochromic naphthopyrans of the invention, alone or together with other photochromic substances, may be incorporated into a polymeric host material such as, but not being limited to, polycarbonate, polyurethane, polyacrylate, polymethacrylate, polystyrene or a copolymer of polyacrylate or polymethacrylate with polystyrene.
The aforementioned photochromic compounds of the invention or its mixtures can also be incorporated into organic plastic articles such as, for example, optical lenses, e.g. ophthalmic and piano lenses, visors, car windshields or other articles, giving high optical density of color on irradiation with sunlight. The incorporation of the photochromic compounds can be carried out by any conventional method known in the art, for example, by molding techniques, e.g., injection-moulding, press-moulding or by polymerization techniques, e.g., by thermal polymerization of a photochrome solution in a polymerizable monomer containing a catalyst, for example, azo-isobutyronytryl, giving free radicals on heating. Microencapsulation techniques can also be employed. A photochromic compound may be incorporated in a polymer host also by thermodiffusion through the lens surface. In one embodiment, a mixture of different photochromes can be incorporated into a plastic object.
The blends of the photochromes of the invention with polymers and polymer compositions provide high quality photochromic plastic objects, especially plastic lenses with high optical density on photoactivation, high fatigue resistance and fast decoloration in the dark.
Thus, in another embodiment, the present invention further relates to a photochromic plastic -organic article, preferably a plastic lens, comprising a plastic object containing the aforementioned photochrome with a photochrome known in the art and/or comprising other ingredients such as plasticizers, light stabilizers and materials for the photochrome micro-encapsulation.


REFERENCES:
patent: WO 99/31081 (1999-06-01), None
patent: WO 01/10858 (2001-02-01), None

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