Naphthopyrans with a heterocycle in the 5, 6-position,...

Details Naphthopyrans with a heterocycle in the 5, 6-position,... Naphthopyrans with a heterocycle in the 5, 6-position,...

2000-11-03

2004-04-13

Lovering, Richard D. (Department: 1712)

Compositions

Light transmission modifying compositions

Displaying color change

C351S163000, C524S094000, C524S109000, C524S110000, C524S111000, C548S421000, C549S248000, C549S383000

Reexamination Certificate

active

06719925

ABSTRACT:

This application claims the benefit of priority of FR Application No. 99 13791, filed Nov. 4, 1999, entitled Naphthopyrans With A Heterocycle In The 5,6-Position, Preparation, And (Co)Polymer Compositons And Matrices Containing Them, of Breyne et al.
The present invention relates to novel compounds of the fused naphthopyran type which have photochromic properties in particular. It further relates to the photochromic compositions and photochromic ophthalmic articles (for example lenses) containing said naphthopyrans. The invention further encompasses the preparation of these novel compounds.
Photochromic compounds are capable of changing color under the influence of a poly- or monochromatic light (for example UV) and of returning to their initial color when the light irradiation ceases or under the influence of temperature and/or a different poly- or monochromatic light from the first.
Photochromic compounds are applicable in various fields, for example for the manufacture of ophthalmic lenses, contact lenses, sunglasses, filters, optics for movie cameras, ordinary cameras or other optical and observational devices, glass panes, decorative objects or display elements, or for the storage of data by optical recording (coding).
In the field of ophthalmic optics and particularly spectacles, a photochromic lens, comprising one or more photochromic compounds, must have:
a high transmission in the absence of ultraviolet,
a low transmission (high colorability) under solar irradiation,
appropriate coloration and decolorization kinetics,
a tint acceptable to the consumer (preferably gray or brown), preferably with maintenance of the chosen tint during the coloration and decolorization of the lens,
maintenance of the performance characteristics and the properties over the temperature range 0-40° C., and
a substantial durability because the intended objectives are sophisticated and hence expensive corrective lenses.
These lens characteristics are in fact determined by the active photochromic compounds which the lens contains, it also being necessary for said compounds to be perfectly compatible with the organic, mineral or even hybrid substrate of which the lens is made.
It should furthermore be noted that, to obtain a gray or brown tint, it may be necessary to use at least two photochromic substances of different colors, i.e. having different maximum absorption wavelengths in the visible. This association makes yet more demands on the photochromic compounds. In particular, the coloration and decolorization kinetics of the (two or more) associated active photochromic compounds must be substantially identical. The same applies to their stability over time and also to their compatibility with a plastic or mineral substrate.
The benzopyrans or naphthopyrans described in the following patents or patent applications may be mentioned among the numerous photochromic compounds described in the prior at: U.S. Pat. No. 3,567,605, U.S. Pat. No. 3,627,690, U.S. Pat. No. 4,826,977, U.S. Pat. No. 5,200,116, U.S. Pat. No. 5,238,981, U.S. Pat. No. 5,411,679, U.S. Pat. No. 5,429,744, U.S. Pat. No. 5,451,344, U.S. Pat. No. 5,458,814, U.S. Pat. No. 5,651,923, U.S. Pat. No. 5,645,767, U.S. Pat. No. 5,698,141, U.S. Pat. No. 5,783,116, WO-A-95 05382, FR-A-2 718 447, WO-A-96 14596 and WO-A-97 21698, said compounds having the reduced formulae below:
U.S. Pat. No. 5,783,116 more specifically describes naphthopyrans of the following general structure:
U.S. Pat. No. 5,811,034 claims the following general structure in particular:
These compounds are said to satisfy the specifications defined above. In reality, although these compounds do indeed have one or more of the desired basic properties, such as a high transmission in the absence of ultraviolet and a high colorability under solar irradiation, none of the compounds described hitherto have the complete combination of desired properties which is necessary for the production of satisfactory articles. In particular, none of these compounds is intrinsically gray or brown and there is still a need to use a complementary photochromic substance in order to obtain one of these two tints.
In this context, it is to the inventors' credit that they took an interest in this type of derivative as a basis for the development of novel photochromic substances, and that they are proposing a novel family of molecules possessing particularly advantageous photochromic properties.
Thus, according to a first feature, the present invention relates to compounds of formula (I) or (II):
in which:
X is an oxygen or NR
6
, R
6
being a hydrogen, a linear or branched alkyl group containing from 1 to 12 carbon atoms, a cycloalkyl group containing from 3 to 12 carbon atoms or an aryl or heteroaryl group containing in its basic structure 6 to 24 carbon atoms or, respectively, 4 to 24 carbon atoms and at least one heteroatom selected from sulfur, oxygen and nitrogen, said basic structure optionally being substituted by at least one substituent selected from a linear or branched alkyl containing 1 to 12 carbon atoms, a linear or branched alkoxy containing 1 to 12 carbon atoms, a halogen and a hydroxy;
R
4
and R
5
, which are identical or different, independently are a hydrogen, a hydroxy or a linear or branched alkyl group containing 1 to 6 carbon atoms, or together form an oxo group (═O);
R
1
and R
2
, which are identical or different, independently are:
hydrogen,
a linear or branched alkyl group containing from 1 to 12 carbon atoms,
a cycloalkyl group containing from 3 to 12 carbon atoms,
an aryl or heteroaryl group containing in its basic structure 6 to 24 carbon atoms or, respectively, 4 to 24 carbon atoms and at least one heteroatom selected from sulfur, oxygen and nitrogen, said basic structure optionally being substituted by at least one substituent selected from the group of substituents given below:
a halogen, especially fluorine, chlorine or bromine,
a hydroxy,
a linear or branched alkyl group containing from 1 to 12 carbon atoms,
a linear or branched alkoxy group containing from 1 to 12 carbon atoms,
a haloalkyl or haloalkoxy group corresponding respectively to the above (C
1
-C
12
)alkyl or (C
1
-C
12
)alkoxy groups substituted by at least one halogen atom, especially a fluoroalkyl group of this type,
a phenoxy or naphthoxy group optionally substituted by at least one linear or branched alkyl or alkoxy group containing from 1 to 12 carbon atoms,
a linear or branched alkenyl group containing from 2 to 12 carbon atoms, especially the vinyl group or the allyl group,
a group —NH
2
,
a group —NHR, R being a linear or branched alkyl group containing from 1 to 6 carbon atoms or a phenyl optionally substituted by at least one linear or branched alkyl containing from 1 to 6 carbon atoms,
a group:
 R′ and R″, which are identical or different, independently being a linear or branched alkyl group containing from 1 to 6 carbon atoms or a phenyl optionally substituted by at least one linear or branched alkyl containing 1 to 6 carbon atoms, or, together with the nitrogen atom to which they are bonded, being a 5- to 7-membered ring which can contain at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen optionally being substituted by a group R′″, which is a linear or branched alkyl group containing from 1 to 6 carbon atoms, or
a methacryloyl group or an acryloyl group,
an aralkyl or heteroaralkyl group in which the alkyl group is linear or branched and contains from 1 to 4 carbon atoms and in which the aryl or heteroaryl moiety is as defined above for the aryl or heteroaryl group, or
said two substituents R
1
and R
2
together form an adamantyl, norbornyl, fluorenylidene, di(C
1
-C
6
)alkylanthracenylidene or spiro(C
5
-C
6
)cycloalkylanthracenylidene group, said group optionally being substituted by at least one of the substituents listed above for R
1
and R
2
as an aryl or heteroaryl group;
R
3
, which are identical or different, independently are:
a halogen, especially fluorine, chlorine or bromine,
a hydroxy,
a line

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