Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-02-07
1997-06-10
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548260, C07D24920
Patent
active
056377266
DESCRIPTION:
BRIEF SUMMARY
INTRODUCTION TO THE INVENTION
This invention relates to compounds which can be included in polymers to impart ultraviolet absorbing properties. The invention also encompasses ocular devices which absorb ultraviolet radiation, and to their production from ultraviolet absorbing compounds, such as by copolymerizing the compounds with suitable reactive monomers.
Contact lenses containing compounds for absorbing ultraviolet (u.v.) light have been on the market for several years. Such lenses are useful to all who live in areas where bright sunlight is common. As u.v. radiation is likely to be a cause of cataracts and senile macular degeneration, everyone who wears contact lenses can benefit from the type which absorb this radiation. Younger persons, whose eye lenses transmit more ultraviolet radiation than do those of older persons, also should be concerned with providing additional protection.
Ultraviolet absorbing lenses are especially useful for those who have had the natural lens of the eye removed, since the natural lens has u.v. absorption properties that help to protect the interior of the eye. Hence, u.v. absorbing intraocular lenses are also highly desirable, since such lenses are implanted in place of the eye's natural lens.
Loshaek discovered the use of polymerizable u.v. absorbers for producing contact and intraocular lenses in the early 1970's, e.g., as shown in U.S. Pat. No. Re. 33,477. More recently, substituted 2-phenyl benzotriazole compounds having a polymerizable acrylic group have been used to produce contact lenses, e.g., as in U.S. Pat. No. 4,716,234 to Dunks et al. The u.v. absorption technology has been applied primarily to rigid, gas permeable lenses; the commercially available soft lenses typically do not contain u.v. absorbers.
The present invention is predicated on use of substituted 2-phenyl benzotriazole compounds having a styrene group to form polymers exhibiting high degrees of u.v. absorption. These u.v. absorbing compounds have several advantages in producing polymers, particularly those used for contact lenses: absorption at the lower wavelengths, i.e, from 50 to 250 nanometers. approximating that of the natural lens of the eye. to achieve useful levels of u.v. absorption.
SUMMARY OF THE INVENTION
The invention includes compounds having the formula: ##STR1## wherein R.sup.1 is a halogen or C.sub.1 -C.sub.6 straight or branched chain alkoxy group; and R.sup.2 is a --(CH.sub.2).sub.3 O--, --(CH.sub.2).sub.2 O--, --CH(CH.sub.3)CH.sub.2 O--, --CH.sub.2 CH(CH.sub.3)O--, --(CH.sub.2).sub.3 OCH.sub.2 --, --(CH.sub.2).sub.2 OCH.sub.2 --, --CH(CH.sub.3)CH.sub.2 OCH.sub.2 --, or --C.sub.2 CH(CH.sub.3)OCH.sub.2 -- group.
Other aspects of the invention include polymers produced by copolymerizing the inventive compounds with one or more other monomers, polymers which include the inventive compounds in physical admixture or reacted with pendant groups, and contact and intraocular lenses made from such polymers .
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a graphical representation of the results of the experiment described in Example 3.
FIG. 2 is a graphical representation of the results of the experiment described in Example 4.
FIG. 3 is a graphical representation of the results of the experiment described in Example 5.
DETAILED DESCRIPTION OF THE INVENTION
In the following description and claims, the term "percent" will be used to represent percentage by weight, unless the context indicates otherwise.
Ocular devices contemplated in connection with the present invention include, without limitation, windows, lenses for eyeglasses and instruments such as binoculars, goggles, face shields, contact lenses, intraocular lenses and the like. Contact lenses can include both those for correcting defective visual acuity and the so-called "bandage lenses" which are used in treating eye disorders, as well as the purely cosmetic lenses used for purposes such as changing the apparent eye color.
As noted above, the compounds of the present invention are those having the following structural for
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Collins Theresa A.
Mulvihill John T.
Oswecki Jane C.
Richter Johann
Wesley-Jessen Corporation
Yang Frank Z.
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