Light filters comprising a naturally occurring chromophore and derivatives thereof

A technology of chromophores and derivatives, applied in optics, optical components, instruments, etc., can solve the problems of not providing versatility and adjustability

Active Publication Date: 2012-12-12
BENZ RES & DEV
View PDF15 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, this system is limited to the oxidative polymerization of 3-hydroxykynurenine and does not offer versatility and tunability
Also, the system only offers blue light filtering capabilities

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Light filters comprising a naturally occurring chromophore and derivatives thereof
  • Light filters comprising a naturally occurring chromophore and derivatives thereof
  • Light filters comprising a naturally occurring chromophore and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Embodiment 1 prepares 2-chloroethyl methacrylate

[0121]

[0122] A solution of 530 ml (7.91 mol) of 2-chloroethanol and 1210 ml (14.96 mol) of pyridine in 3LEtOAc was cooled to 5° C. in an ice bath and 820 ml (6.71 mol) of acryloyl chloride (tech., 80 %) in 1 L of EtOAc such that the internal temperature was kept below or equal to 17 °C. This took 2.5 hours. The reaction mixture was slowly cooled to room temperature overnight. The slurry was then filtered and the filter cake of pyridine hydrochloride was washed with about 3 L of EtOAc. The filtrate was divided into 3 approximately equal fractions and each fraction was thus refined. Each was extracted with 2 x 1 L of 2N HCI, 2 x 500 ml of DI water and 1 x 500 ml of 5 wt% sodium bicarbonate, then the three fractions were combined and dried over anhydrous sodium sulfate (764 g). After filtration, the EtOAc solution was treated with 11.1 g hydroquinone and concentrated in vacuo to yield 1245.7 g pale yellow oil. ...

Embodiment 2

[0123] Example 2 Preparation of kynurenine chromophore compounds

[0124]

[0125] A reaction mixture containing 103.0 g (681 mmol) of 2-amino-3-hydroxyacetophenone, 125.1 g (842 mmol) of 2-chloroethyl methacrylate and 122.6 g (887 mmol) of potassium carbonate in 930 ml of DMSO was processed for 5 hours Warm to 85°C and stir overnight (16 hours) at this temperature. After this time, TLC (silica gel, hexane:acetone 3:1) showed the reaction was complete. After cooling to 48 °C, the reaction mixture was partitioned between 2 L of DI water and 500 ml of toluene. After a second 500 ml toluene extraction of the aqueous phase, the combined organic layers were washed twice with 1 L of 10 wt% potassium carbonate. The organic phase was then passed through a 1253 g silica gel (70-230 mesh) plug, eluting with 3:1 hexane:acetone until no more product was visible (TLC) leaving the plug. This used 6 L of elution solvent. The eluate was concentrated under vacuum to yield 199 g of amb...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

A composition comprising a polymer backbone and at least one side group, wherein the side group comprises a benzene ring-based chromophore comprising a ketone at the 1-position, a substituted or unsubstituted amino group at the 2-position, and an oxygen atom at the 3-position of the benzene ring having the following formula: wherein R1 is H, an alkyl group, or comprises an amino acid moiety or derivative thereof; R2 and R3 are individually H, alkyl, or any moiety with a vinyl functionality; R4 is an alkyl group, any moiety with a vinyl functionality, a counterpart alkyl²ne group, or a sugar moiety; and X is an optional electron-donating group linked to the benzene ring at the 4, 5, or 6 position. The chromophore is a kynurenine-based compound. Methods of making and using the composition are also provided. The composition can be used in an ophthalmic lens or device for protecting the retina by blocking UV rays and filtering violet rays.

Description

[0001] This application claims priority to US Application Serial No. 60 / 893,065, filed March 5, 2007, which is incorporated by reference in its entirety for all purposes. Background technique [0002] There are various dyes proposed for use as polymerizable compounds for the coloring of optical plastics for lenses and ocular devices. Most of these relate to various biphenylazo or triphenyldiazo compounds. These are often claimed to provide UV protection as well as blue light blocking capabilities due to their yellow or orange color. Since the human crystalline lens is yellowish in youth and yellowish brown in old age, these dyes serve a purpose of providing UV protection in addition to their blue light filtering ability. [0003] Additionally, U.S. Patent 6,825,975 (Gallas) discloses optical filters prepared by oxidatively polymerizing 3-hydroxykynurenine to form complex visible light-absorbing compounds having broadly different Acid absorption spectrum. Furthermore, this s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): G02B5/22
CPCC07C225/22G02B5/208G02B5/223G02B1/043C08K5/18C08F20/34G02B5/22
Inventor 帕特里克·H·宾视约瑟·A·奥斯
Owner BENZ RES & DEV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap