Copolymerizable methine and anthraquinone compounds and articles containing them

a technology of polymerizable methine and anthraquinone, which is applied in the field of polymerizable ultraviolet light absorbers, yellow colorants, can solve the problems of increasing production and materials costs, unsuitable for use in artificial lens materials, and complicated manufacturing processes, so as to reduce the potential for compound leaching out of materials, reduce the intensity of violet-blue light transmitted, and the effect of reducing the absorption properties

Inactive Publication Date: 2006-06-01
ADVANCED MEDICAL OPTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0024] By bonding the compound to the polymer, the potential for the compound leaching out of the material is diminished or eliminated. As a result, in some embodiments these compounds are used in transparent materials to decrease the intensity of violet-blue light transmitted through them. These transparent materials with one or more of the bondable yellow compounds and / or bondable UVAs incorporated in them may be extracted with organic solvents to remove unreacted monomers, low molecular weight oligomers and low molecular weight polymers, as well as other impurities, and then used to make ocular lenses such as intraocular lenses (IOLs), contact lenses, eyeglasses and other windows. These transparent materials containing yellow compounds may also be used to make lens coating materials. Surprisingly, the methine chromophores of the present invention do not lose their absorbance properties upon free radical polymerization. This is surprising since the chromophoric unit is an ethylenically unsaturated moiety so that the polymerization reaction involving the chromophoric unit would be expected to result in loss of the absorption properties.

Problems solved by technology

If the brain is stimulated by signals caused by the visible light that has not been transmitted for many years, discomfort can result.
Although yellow colorants exist, many such colorants are unsuitable for use in artificial lens material due to their tendency to leach out of the IOL after it is inserted in the eye or during solvent extraction associated with lens manufacture.
One obstacle of such efforts has been finding a polymerizable compound that will produce IOLs having an absorption profile that carefully matches that of the aged human lens, especially in the visible spectrum.
If the IOL absorbs less in the visible spectrum, the discomfort discussed above can result.
Another obstacle that such efforts have faced has been the need to use a combination of multiple compounds to achieve a careful match with the human lens.
Use of multiple compounds can result in a more complicated manufacturing process, along with increased production and materials costs.

Method used

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  • Copolymerizable methine and anthraquinone compounds and articles containing them
  • Copolymerizable methine and anthraquinone compounds and articles containing them
  • Copolymerizable methine and anthraquinone compounds and articles containing them

Examples

Experimental program
Comparison scheme
Effect test

example 104

[0127]

[0128] To a clean, dry 1 L 4-neck flask equipped with a mechanical stirrer, heating mantle, thermocouple, addition funnel and a Dean-Stark trap were added 99 g of methyl cyanoacetate (1.0 mol). The reaction vessel was stirred under an atmosphere of dry nitrogen and heated to 95° C. To the reaction vessel were added 61.1 g (1.0 mol) of ethanolamine at a dropwise rate while removing low boilers via the Dean-Stark trap. An exotherm occurred early during the addition and the temperature increased to 105° C. The addition was complete in about 45 minutes and the reaction vessel temperature was increased to 150° C. After about 1 h low boilers were no longer being collected in the Dean-Stark trap. The reaction solution was allowed to cool to about 85° C. and 125 mL of cyclohexane was added at a rapid, dropwise rate. The cyclohexane was decanted. A fresh 75 mL of cyclohexane were added and the warm mixture was transferred to a 600 mL beaker. The product began to solidify to give a waxy...

example 105

[0129]

[0130] To a clean, dry 500 mL flask equipped with a heating mantle and addition funnel were added 200 mL of DMF and 50.7 g of N-phenylthiomorpholine-S,S-dioxide (0.2 mol, available from Eastman Chemical Company). The reaction vessel was purged with nitrogen and 20.5 mL of phosphorus oxychloride (0.2 mol) were added at such a rate to keep the temperature from exceeding 35° C. The reaction vessel was heated to 80-90° C. and stirred for about 4 h. The reaction mixture was allowed to cool to room temperature and poured into a mechanically stirred ice water mixture (1 L) containing 100 mL of concentrated ammonium hydroxide. A white precipitate formed that was collected by suction filtration and washed with water. The cake was allowed to dry on the filter overnight to give 54.4 g of product.

example 106

[0131]

[0132] To a 500 mL round-bottomed flask equipped with a mechanical stirrer, reflux condenser and heating mantle were added methanol (175 mL), 18.0 g of product from Example 105 (75.0 mmols) and 10.4 g of product from Example 104 (80.0 mmols). The mixture was heated to reflux and stirred for 3 h then allowed to cool to room temperature, at which time a precipitate formed. The precipitate was collected by suction filtration, washed with cold methanol and allowed to dry on the filter overnight to give 19.75 g of light yellow compound.

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Abstract

This invention relates to polymerizable ultraviolet light absorbers and yellow colorants and their use in ophthalmic lenses. In particular, this invention relates to polymerizable ultraviolet light absorbing methine compounds and yellow compounds of the methine and anthraquinone classes that block ultraviolet light and/or violet-blue light transmission through ophthalmic lenses.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Patent Application Ser. No. 60 / 629,556 filed Nov. 22, 2004.FIELD OF THE INVENTION [0002] This invention relates to polymerizable ultraviolet light absorbers, yellow colorants and their use in ophthalmic lenses. In particular, this invention relates to polymerizable ultraviolet light absorbing methine compounds and polymerizable yellow compounds of the methine and anthraquinone classes that block ultraviolet light and / or violet-blue light transmission through ophthalmic lenses. BACKGROUND OF THE INVENTION [0003] The sun freely emits ultraviolet (UV), visible and infrared (IR) radiation, much of which is absorbed by the atmosphere. Solar radiation that is transmitted through the atmosphere and reaches the earth's surface includes UV-A radiation (320-400 nm), UV-B radiation (290-320 nm), visible light (400-700 nm) and near IR radiation (700-1400 nm). The ocular l...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D279/12C09B1/16A61F2/00C07D307/02
CPCA61L27/14A61L2430/16C07C235/34C07C237/06C07C255/41C07C255/42C07D207/408C07D209/48C07D263/56C07D295/155C07D307/16G02B1/041C07C233/55C07C237/20C07C255/44C07C271/12
Inventor PEARSON, JASON CLAYWEAVER, MAX ALLENFLEISCHER, JEAN CARROLLKING, GREGORY ALLAN
Owner ADVANCED MEDICAL OPTICS
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