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Polymerisable yellow dye, ophthalmic lens material and ophthalmic lens

A technology of yellow dyes and ophthalmic lenses, which is applied in the field of yellow dyes, can solve problems such as the inability to apply ophthalmic lenses, and achieve good blue light blocking rate, avoid damage, and good physical properties

Active Publication Date: 2014-01-01
BENQ MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, general yellow dyes are water-soluble and can only be applied to ophthalmic lenses made of hydrogel, but not to ophthalmic lenses made of silicone hydrogel

Method used

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  • Polymerisable yellow dye, ophthalmic lens material and ophthalmic lens
  • Polymerisable yellow dye, ophthalmic lens material and ophthalmic lens
  • Polymerisable yellow dye, ophthalmic lens material and ophthalmic lens

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: Preparation of yellow dye (I)

[0054]

[0055] Under nitrogen, add 2.5 grams of 4-hydroxyazobenzene and 40 milliliters of dichloromethane into a round-bottomed flask, accurately weigh 0.002 grams of dibutyltin dilaurate and 2.0 grams of isocyanoethyl methacrylate, Add to round bottom bottle. After stirring for 5 hours, a large amount of water was added to wash the reaction product, and after dehydration and filtration, dichloromethane was removed to obtain yellow dye (I).

[0056] of yellow dye (I) 1 The results of H-NMR analysis are as follows:

[0057] 1 H-NMR (400MHz, CDCl 3 ): δ7.93-7.84(m, 4H), 7.51-7.43(m, 3H), 7.28-7.24(m, 2H), 6.29(s, 1H), 5.62(s, 1H), 5.37(1H, NH) ), 4.31(m, 2H), 3.62(m, 2H), 1.97(s, 3H).

Embodiment 2

[0058] Example 2: Preparation of yellow dye (II):

[0059]

[0060] Under nitrogen, 2 g of 4-hydroxyazobenzene, 1.6 g of methacrylic acid, 2.36 g of 1-ethyl-3-3-dimethylaminopropylcarbodiimide, 0.15 g of 4-dimethylamino Pyridine and 30 mL of dichloromethane were added to a round bottom flask. After stirring for 12 hours, 20 ml of water was added to a round-bottomed flask for extraction. After collecting the organic layer, the yellow dye (II) was obtained after dehydration, filtration and removal of dichloromethane.

[0061] of yellow dye (II) 1 The results of H-NMR analysis are as follows:

[0062] 1 H-NMR (400MHz, CDCl 3 ): δ7.88(m, 4H), 7.43(m, 3H), 7.20(m, 2H), 6.31(s, 1H), 5.72(s, 1H), 2.01(s, 3H).

Embodiment 3

[0063] Example 3: Preparation of yellow dye (III):

[0064]

[0065] Under nitrogen conditions, add 1 g of Disperse Yellow 3 and 40 ml of dichloromethane into a round-bottomed flask, and accurately weigh 0.001 g of dibutyltin dilaurate and 0.6 g of isocyanoethyl methacrylate. Add to round bottom bottle. After stirring for 5 hours, a large amount of water was added to wash the reaction product, and after dehydration, filtration and removal of dichloromethane, yellow dye (III) was obtained.

[0066] of yellow dye (III) 1 The results of H-NMR analysis are as follows:

[0067] 1 H-NMR (400MHz, CDCl 3 ): δ7.93-7.84(m, 4H), 7.51-7.43(m, 3H), 7.28-7.24(m, 2H), 6.29(s, 1H), 5.62(s, 1H), 5.37(1H, NH) ), 4.31(m, 2H), 3.62(m, 2H), 1.97(s, 3H).

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Abstract

The invention relates to a polymerisable yellow dye which is used for ophthalmic lenses and is capable of reducing or preventing blue light from penetrating ophthalmic lenses. The chemical structure is represented by formula (I), wherein R1 represents hydrogen or -NHCOCH3, R2 represents hydrogen or C1-C3 alkyl, R3 and R4 represent hydrogen or -OCOR5 independently, R5 represents isopropenyl or substituted isopropenyl-R6-(R7O)n-COC(CH3)CH2, R6 represents -NH- or a structure shown in the description, R7 represents C1-C5 alkylene, and n is an integer ranging from 1 to 40. An ophthalmic lens prepared by copolymerization of the polymerisable yellow dye and an ophthalmic lens moulding material possesses excellent blue light blocking rate.

Description

technical field [0001] This invention relates to a polymerizable yellow dye, and in particular to a polymerizable yellow dye for use in ophthalmic lenses to block or reduce the intensity of blue light passing through the lens. Background technique [0002] Solar radiation in the surrounding environment can cause damage to eyesight. The sun emits ultraviolet (UV), visible light (visible) and infrared (IR), and most of the infrared rays will be absorbed by the atmosphere. : UV-A radiation (wavelength between about 300-400nm), visible light (wavelength between about 400-700nm) and near infrared (wavelength between about 700-1400nm). When the human eye is healthy, it blocks near-infrared rays and most visible light from reaching the retina. [0003] In recent years, it has been known that blue light (wavelength between about 450-500nm) in visible light may cause damage to the retina. In nature, the main source of blue light is the sun. However, most electronic products, such a...

Claims

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Application Information

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IPC IPC(8): C09B43/20C09B43/26C08F220/28C08F290/06C08F283/12G02B1/04
Inventor 詹凡丹张修豪
Owner BENQ MATERIALS
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