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(meth)acrylate compound, and photochromic curable composition containing said (meth)acrylate compound

A curable composition, photochromic technology, applied in optics, organic chemistry, optical components, etc., can solve the problems of slow fading speed, lens peeling, blocked lens surface polymerization, etc., to achieve improved effect, high durability, Excellent photochromic effect

Inactive Publication Date: 2014-07-02
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In addition, using the most common sebacic acid (1,2,2,6,6-pentamethyl-4-piperidinyl) diester with 2,2,6,6-tetramethyl-4 - In the case of a piperidinyl hindered amine compound, depending on the compounding amount, the hindered amine compound gradually oozes out from the lens substrate or coating, causing the problem that the surface of the lens substrate or coating becomes cloudy
In addition, especially in the kneading method, depending on the compounding amount, the following problems also arise during the polymerization and curing of the lens: the phenomenon that the lens is easily peeled off from the glass mold (mold), the polymerization of the lens surface is hindered and the become defective lenses
However, according to the studies of the inventors of the present invention, it was determined that not only the original durability improvement effect was not sufficiently exhibited, but also a new problem of reduced photochromic properties, especially a slowed fading speed, occurred.

Method used

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  • (meth)acrylate compound, and photochromic curable composition containing said (meth)acrylate compound
  • (meth)acrylate compound, and photochromic curable composition containing said (meth)acrylate compound
  • (meth)acrylate compound, and photochromic curable composition containing said (meth)acrylate compound

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Embodiment

[0571] Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited to these examples.

[0572]

Synthetic example 1

[0574] Synthesis of (1,2,2,6,6-pentamethyl-4-piperidinyl) 2-acryloyloxyethylsuccinate (abbreviation: HM-01):

[0575] Set a stirring blade, a thermometer, and a dropping funnel on a 500mL four-neck flask, and add the following substances.

[0576]

[0577] The mixture was cooled to 0°C, and 12.1 g (0.012 mol) of dicyclohexylcarbodiimide was added little by little. The mixture was stirred at 0 to 5°C for 10 minutes, and further stirred at room temperature for 1 night. After filtering the precipitated white solid, 400 mL of toluene was added to the filtrate, followed by washing with 400 mL of water three times. Furthermore, the organic layer was washed twice with 200 mL of 0.5N hydrochloric acid water, and the washing liquid was collected, neutralized with 5% aqueous sodium carbonate solution, and extracted with toluene. After drying over magnesium sulfate, the solvent was distilled off. The obtained pale yellow liquid was purified with a neutral alumina column {developing...

Synthetic example 2

[0583] Synthesis of acryloyloxypolycaprolactone (c≈2) carboxylic acid (1,2,2,6,6-pentamethyl-4-piperidinyl) ester (abbreviation: HM-02):

[0584] Set a stirring blade, a thermometer, and a dropping funnel on a 500mL four-neck flask, and add the following substances.

[0585]

[0586]

[0587] The mixture was cooled to 0°C, and 12.1 g (0.012 mol) of dicyclohexylcarbodiimide was added little by little. The mixture was stirred at 0 to 5°C for 10 minutes, and further stirred at room temperature for 1 night. After filtering the precipitated white solid, 400 mL of toluene was added to the filtrate, followed by washing with 400 mL of water three times. Furthermore, the organic layer was washed twice with 200 mL of 0.5N hydrochloric acid water, and the washing liquid was collected, neutralized with 5% aqueous sodium carbonate solution, and extracted with toluene. After drying over magnesium sulfate, the solvent was distilled off. The obtained pale yellow liquid was purified w...

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Abstract

A photochromic curable composition that contains a (meth)acrylate compound represented by the following formula (1-X1); (wherein Y is an oxygen atom or a divalent group represented by —NH—, R1 and R2 are hydrogen atoms or methyl groups, R3 is an alkylene group having 1 to 6 carbon atoms, R4 is an alkylene group having 1 to 6 carbon atoms, a cycloalkylene group having 3 to 8 carbon atoms and which may include a double bond, or an arylene group having 6 to 10 carbon atoms, and a is a positive number of 1 to 20), other radically polymerizable monomers and a photochromic compound. The invention provides a lens that features excellent durability and high photochromic property free of the problems of turbidity in the surfaces of the lens caused by bleed out or the peeling in the step of production.

Description

technical field [0001] The present invention relates to a novel (meth)acrylate compound and a novel curable composition useful for producing a photochromic optical article containing the (meth)acrylate compound. Background technique [0002] Photochromic glasses are glasses whose lenses are quickly colored outdoors when exposed to sunlight, which includes ultraviolet rays, and function as sunglasses, and fade indoors without such light and become transparent ordinary glasses. role. The demand for photochromic glasses has increased dramatically in recent years. [0003] As for photochromic spectacle lenses, plastic lenses are particularly preferable from the viewpoint of light weight and safety. Imparting photochromic properties to such plastic lenses is usually carried out by compounding an organic photochromic compound with a polymerizable monomer or lens. [0004] As a compounding method, a method of dissolving a photochromic compound in a polymerizable monomer and poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/36C07D211/46C07D211/58C08F2/44C08L33/14
CPCC08F220/36G02B1/04C07D211/46C08F2/44C08F2/48C07D211/58C08L33/14C08F220/286C08F220/365C08F222/1025C08F222/103C08F222/102C08F220/325C08F20/36
Inventor 竹中润治百田润二
Owner TOKUYAMA CORP
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