Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2000-02-14
2001-09-18
Sanders, Kriellion (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S099000, C524S110000, C523S106000, C252S586000
Reexamination Certificate
active
06291561
ABSTRACT:
The object of the present invention is to produce particularly efficient photochromic compositions which incorporate two photochromic compounds within its matrix. The invention involves using the two photochromic compounds jointly. The invention is based on a double selection insofar as the two photochromic compounds were selected on the one hand for their intrinsic properties and on the other, for their mutual compatibility and their complementarity (in respect of the tint obtained).
The present invention finally relates to (co)polymer matrices which incorporate one or the other, advantageously both photochromic compounds as well as finished products—glazings, optical device, ophthalmic or solar article etc., constituted wholly or in part of such matrices.
The photochromic compounds are capable of changing color under the influence of a poly- or mono-chromatic light (UV for example) and of returning to their initial color when the luminous irradiation ceases, or under the influence of temperature and/or poly- or mono-chromatic light different from the first.
The photochromic compounds find applications in various fields, for example, for the manufacture of ophthalmic lenses, contact lenses, solar protection glasses, filters, camera optics or photographic apparatus optics or other optical devices and observation devices, glazings, decorative objects, bill elements or even for information storage by optical inscription (coding).
In the field of ophthalmic optics, and in particular the spectacles trade, a photochromic lens which comprises one or more photochromic compounds must have:
a high transmission in the absence of ultraviolets,
a low transmission (high colorability) under solar irradiation,
adapted coloration and discoloration kinetics,
a tint acceptable to the consumer (gray or brown preferably) with a maintenance of the chosen tint during the coloration and the discoloration of the lens,
a maintenance of the performances, the properties, within a temperature range of 0°-40° C.,
a significant durability, since these objectives sought are sophisticated corrective lenses and therefore expensive.
These lens characteristics are in fact determined by the active photochromic compounds which they contain; compounds which must furthermore be perfectly compatible with the organic or inorganic support which constitutes the lens.
Moreover, it is to be noted that obtaining a gray or brown tint—tints acceptable to the consumer—necessitates the use in practice of at least two photochromes of different colors, i. e. having distinct maximal absorption wavelengths in the visible. This association further imposes other requirements of the photochromic compounds. In particular, the coloration and discoloration kinetics of the (two or more) associated active photochromic compounds must be essentially identical. It goes without saying for their stability with time and also for their compatibility with a plastic or inorganic support.
Amongst the numerous photochromic compounds described in the prior art, benzopyrans and naphthopyrans may be cited which are described in patents U.S. Pat. Nos. 3,567,605, 3,627,690, 4,818,096, 4,826,977, 5,200,116, 5,238,981, 5,458,814, WO 96/04576 and in the Research Disclosure No. 36144, which are of the formula below:
These compounds claim to satisfy the specifications defined above. In reality, if these compounds really do have one or more of the basic properties sought, such as a high transmission in the absence of ultraviolets and a high colorability under solar irradiation, none of them have the complete combination of the properties sought which are necessary for the production of satisfactory articles which may be manufactured industrially.
The Applicant, confronted with the specifications proposes a novel solution which is based on a double selection.
It is in fact to the credit of the Applicant to have selected on the one hand a photochromic compound (compound (I) of the invention which exhibits a violet color) amongst the compounds described in its patent application FR 96 09384, which has not yet been published, and on the other hand, a photochromic compound (compound (II) of the invention which exhibits a yellow color) amongst the compounds described in the application WO-A-94 22850; compounds ((I) and (II)), both efficient per se, and whose association, in addition, has revealed to be particularly interesting insofar as the two compounds, which are perfectly compatible, are complementary in exhibiting a gray tint (acceptable to the consumer).
Thus, according to its first object, the invention relates to a photochromic composition incorporating
2-(p-dimethylaminophenyl)-2-(p-methoxyphenyl)-5-methyl-7,9-dimethoxy-[2H]-naphtho[1,2-b]pyran (compound (I)),
and
3-(p-methoxyphenyl)-3-phenyl-6-morpholino-3H-naphtho-[2,1-b]pyran (compound (II)).
The photochromic composition advantageously contains compounds (I) and (II) in a compound (I)/compound (II) weight ratio between 7 and 10 (more advantageously still between 8 and 9). The best results of the exhibition of the gray tint are within the context of this advantageous variant.
According to its first object, the present invention therefore relates to the joint use of 2-(p-dimethylaminophenyl)-2-(p-methoxyphenyl)-5-methyl-7,9-dimethoxy-[2H]-naphtho[1,2-b]pyran (compound (I)) and 3-(p-methoxyphenyl)-3-phenyl-6-morpholino-3H-naphtho-[2,1-b]pyran (compound (II)) as photochromic agents; the two photochromic agents being advantageously used in a compound (I)/compound (II) weight ratio between 7 and 10 (more advantageously still between 8 and 9). Such a joint use is generally made within a polymeric matrix to which it is desired to confer photochromic properties.
Such a joint use has revealed to be particularly interesting insofar as the photochromic compounds (compound (I) and compound (II)) each have interesting photochromic properties which are compatible (notably from a kinetics and thermal point of view) and complementary with the color (see Examples below).
Compounds (I) and (II) of the photochromic compositions of the invention are now described below in detail. The formula developed for each one of them as well as a means of synthesis of same appear in the Example section of the present text. These compounds are presently claimed.
Compound (I) of the invention consists of 2-(p-dimethylaminophenyl)-2-(p-methoxyphenyl)-5-methyl-7,9-dimethoxy-[2H]-naphtho[1,2-b]pyran.
It is of the general formula of the photochromic naphthopyrans described by the Applicant in its application FR 96 09384 of the Jul. 25, 1996; general formula:
in which at least two of the substituents R
3
to R
6
(advantageously R
3
and R
5
) are C1 to C6 alkoxy groups (advantageously methoxy groups). In application FR 96 09384, R
7
and R
8
are described in a very broad manner, notably as aromatic or polyaromatic groups optionally substituted with at least one C1 to C5 alkoxy, C1 to C5 alkyl, C2 to C12 amine, C6 to C12 aryl, or CF
3
group. In application FR 96 09384, a conventional synthetic route to naphthopyrans is further described:condensation of an appropriately substituted 1-naphthol derivative (substituents R
1
to R
6
) and a propargylic alcohol derivative (substituents R
7
and R
8
).
Within the context of the present invention, the Applicant has selected compound (I)—a violet molecule—of the general formula above in which:
.R
1
=CH
3
.R
2
=R
4
=R
6
=H
.R
3
=R
5
=OCH
3
Surprisingly, the compound has very interesting photochromic properties which are superior to those of its homologues; and has notably:
a weak initial coloration,
a strong colorability with two absorption bands in the visible (see the Table below: &lgr;max 1, &lgr;max 2),
discoloration kinetics adapted (to the application sought),
a low thermal dependence.
The Applicant has notably evaluated the properties in an original matrix which is specified further on in the present text. The matrix is based on a short-chain (meth)acrylate difunctional
Breyne Olivier
Chan You-Ping
Henry David
LaFosse Xavier
Corning S.A.
Nwaneri Angela N.
Rogalskyj Peter
Sanders Kriellion
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