Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-09-20
2003-08-19
Solola, Taofiq (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S384000, C501S013000, C359S241000, C359S244000
Reexamination Certificate
active
06608215
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel naphthopyran-type compounds that have, in particular, photochromic properties. The invention also relates to photochromic compositions and photochromic ophthalmic articles (goggles, lenses and eye-shields, for example) that contain these naphthopyrans. The invention also covers the preparation of these novel naphthopyrans. The photochromic compounds are capable of changing color under the influence of a first 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 light. The invention particularly relates to naphthopyrans having an Oxygen-containing heterocyclic group fused to the naphthopyran.
2. Background of the Art
Photochromism generally concerns the ability of a compound to reversibly change color under different light conditions. One particular type of photochromic phenomenon concerns the reversible change in color of a compound from an original color to a different color when the compound is exposed to a source of ultraviolet radiation, such as solar radiation or light radiated from a mercury or xenon lamp. The photochromic compound fades to the original color within a period of time after the photochromic compound is isolated from the ultraviolet radiation, such as by placing the compound in a dark room.
Photochromic compounds find applications in various fields, such as for the manufacture of ophthalmic lenses, contact lenses, solar protection glasses, goggles, sun screens, filters, camera optics, photographic apparatus optics or other optical devices and observation devices, glazing, decorative objects, currency elements and even for information storage by optical inscription (coding). For example, photochromic compounds, such as naphthopyrans, are incorporated into plastic ophthalmic lenses to effect color changes in the lenses when the lenses are exposed to particular lighting conditions. Additionally, different photochromic compounds may be blended together to create a color effect that is different from respective color effects of the individual photochromic compounds. As an example, a first photochromic compound that turns orange or red when activated by light and a second photochromic compound that turns blue when activated by light may be blended together to form a photochromic mixture that produces a shade of gray when activated by light.
In the field of ophthalic optics, and in particular the field of spectacles, a photochromic lens that comprises one or more photochromic compounds is usually required to have:
a high transmission level in the visible region in the absence of ultraviolet radiation,
a low transmission (high colorability) under solar irradiation (especially with ultraviolet exposure),
desired coloration and discoloration kinetics, e.g., high sensitivity to irradiation and fast bleaching,
a high solubility in hosting materials,
a tint acceptable to the consumer (gray or brown preferably) with the chosen tint maintained during the coloration and the discoloration of the lens,
a maintenance of the performance and properties, within a temperature range of 0-40° C.,
a significant durability, since these objectives sought after are used in sophisticated corrective lenses and are therefore expensive.
These lens characteristics are primarily determined by the active photochromic compounds. These compounds must furthermore be compatible with the organic or inorganic support that constitutes the lens.
Moreover, it is to be noted that obtaining a neutral gray or brown tint may necessitate the use of at least two photochromes of different colors, i.e., two separate compounds having distinct maximal absorption wavelengths in the visible region of the electromagnetic spectrum. The use of combinations of photochromic compounds imposes other requirements on both the individual photochromic compounds and the groups of photochromic compounds. In particular, the coloration and discoloration kinetics of the (two or more) combined active photochromic compounds must be essentially identical. The same applies for their stability with time, and also for their compatibility with a single plastic or inorganic support.
Amongst the numerous photochromic compounds described in the prior art, benzopyrans or naphthopyrans are described in patents or patent applications U.S. Pat. Nos. 3,567,605; 3,627,690; 4,826,977; 5,200,116; 5,238,981; 5,411,679; 5,429,744; 5,451,344; 5,458,814; 5,651,923; 5,645,767; 5,698,141; WO-A-95 05382; WO-A-96-14596; WO-A-97 21698 which are of the reduced formula below:
U.S. Pat. Nos. 5,651,923 and 6,018,059 more specifically describe naphthopyrans having benzofurano or naphthofurano groups fused to the naphthalene ring of naphthopyran (the general structures are shown below).
The various substitutent groups are defined in the various patents and encompass a wide, art-accepted range of combinations of substitutents intended to provide specific physical or photochromic properties. These compounds claim to satisfy the specifications identified above as needed for photochromic compounds. In reality, even if these compounds really do have one or more of the basic properties sought after, such as a high transmission in the absence of ultraviolets and a high colorability under solar irradiation, none of the compounds described hitherto have the complete combination of properties necessary for the production of satisfactory articles. In particular, none of these compounds is intrinsically gray or brown, and the necessity of using an additional photochromes in order to obtain one of these two tints does subsist.
SUMMARY OF THE INVENTION
A novel family of molecules is described having particularly advantageous photochromic properties, such as, two intense absorption bands in the visible range and absorption bands that cover a significant part of visible spectrum (400-700 nm). This novel type of compound adapts or blends well in association with red and/or yellow complementary photochromes to give brown or gray tints.
According to a first aspect of the invention is described Naphthopyran having a central nucleus of the formula:
wherein F is an oxygen-containing 5- to 7-member heterocyclic ring group, its 2,3 or 3,2 positions fused to the f, i, j, or k side of the ring, and
R
1
and R
2
are the atoms or groups providing photochromic properties to the naphthopyran.
This naphthopyran may preferably have R
1
is selected from the group consisting of a hydrogen, a linear or branched alkyl group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, an aryl group of 6 to 24 ring carbon atoms or a heteroaryl group of 4 to 24 carbon atoms and at least one hetero ring atom selected from sulfur, oxygen and nitrogen; and wherein R
1
and R
2
together form an adamantyl, norbornyl, fluorenylidene, di(C1-C6)alkylanthracenylidene or spiro(C5-C6)cycloalkylanthracenylidene group.
Another aspect is a naphthopyran having the central nucleus of the formula:
wherein F is an oxygen-containing 5- to 7-member heterocyclic ring group, its 2,3 or 3,2 positions fused to the f, i, j, or k side of the ring, and
R
1
and R
2
are the atoms or groups necessary to provide photochromic properties to the naphthopyran and R
5
and R
6
are selected from the group consisting of:
a hydrogen,
a halogen,
a linear or branched alkyl group of 1 to 12 carbon atoms,
a cycloalkyl group of 3 to 12 carbon atoms,
a linear or branched alkoxy group of 1 to 12 carbon atoms,
a linear or branched alkenyl or alkynyl group of 1-12 carbon atoms,
a linear or branched alkenyloxy or alkynyloxy group of 1-12 carbon atoms,
an aryl or heteroaryl group, and
an aralkyl or heteroaralkyl group, the alkyl group, which is linear or branched, of 1 to 4 carbon atoms.
According to another aspect of the present invention, naphthopyran compounds of the following formula (I) are described and enabled:
in which:
F is an at least one oxygen-containing, 5
Mark A. Litman & Assoc. P.A.
Solola Taofiq
Vision--Ease Lens, Inc.
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