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Photochromic compound, curable composition containing said photochromic compound, and optical article

A photochromic and compound technology, applied in the direction of color-changing fluorescent materials, optics, optical components, etc., can solve the problem of white turbidity of the cured body, and achieve the effect of good photochromic properties, mechanical properties, and excellent photochromic properties.

Pending Publication Date: 2020-11-24
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The above-mentioned polymer photochromic compound is a technology that has attracted attention in recent years, but it is also known that the cured product containing the polymer photochromic compound becomes cloudy

Method used

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  • Photochromic compound, curable composition containing said photochromic compound, and optical article
  • Photochromic compound, curable composition containing said photochromic compound, and optical article
  • Photochromic compound, curable composition containing said photochromic compound, and optical article

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5

[0563] Embodiment 1~5 (synthesis of photochromic compound of the present invention)

[0564]

[0565] 1st process

[0566] Polyethylene glycol monooleyl ether (36.7 g, 100 mmol) and tosyl chloride (21.0 g, 110 mmol) having a number average molecular weight of 357 were dissolved in pyridine (400 mL), followed by stirring. 1,4-Diazabicyclo[2.2.2]octane (2.2 g, 20 mmol) was dripped there, and it stirred at room temperature for 12 hours. After completion of the reaction, the reaction liquid was added to ice water, and extracted with dichloromethane. The extracted organic layer was washed with 10% hydrochloric acid, and then, the solvent was distilled off to obtain the following formula (16):

[0567] [chem 45]

[0568]

[0569] indicated compound.

[0570] 2nd process

[0571] 4-Hydroxybenzoic acid (6.2 g, 45 mmol), potassium carbonate (18.7 g, 135 mmol) were dissolved in DMF (450 mL). It heated while stirring so that the liquid temperature might become 80 degreeC. The...

Embodiment 2

[0615] 1st process

[0616] Except having used polypropylene glycol (number average molecular weight 2500) instead of the polypropylene glycol monobutyl ether (number average molecular weight 3500) used in the 8th step of Example 1, the reaction was carried out in the same manner as in the 8th step of Example 1, It is obtained by the following formula (26)

[0617] [Chemical 55]

[0618]

[0619] indicated compound.

[0620] 2nd process

[0621] In the 7th step of embodiment 1, in addition to replacing the naphthol compound of the above-mentioned formula (22), the following formula (27) is used:

[0622] [Chemical 56]

[0623]

[0624] Except the naphthol compound represented, carry out similarly, obtain by following formula (28)

[0625] [Chemical 57]

[0626]

[0627] Indicates the chromene precursor.

[0628] 3rd process

[0629] In the ninth step of Example 1, in addition to using the chromene precursor of the above formula (28) instead of the chromene com...

Embodiment 3

[0635] 1st process

[0636] 4,4-Dihydroxybenzophenone (1.0 g, 4.5 mmol), potassium carbonate (1.9 g, 13.5 mmol), and DMF (45 mL) were added, stirred, and heated until the internal temperature became 80°C. After heating, the compound (4.6 g, 9.1 mmol) of the above formula (16) was added dropwise over 1 hour. After dropping, reaction was performed at a liquid temperature of 80° C. for 4 hours. After the reaction, the reaction solution was cooled to room temperature, water was added, and liquid separation was performed using toluene. After the organic solvent was distilled off, the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform-ethyl acetate mixed solvent) to obtain the following formula (30):

[0637] [Chemical 59]

[0638]

[0639] indicated compound.

[0640] 2nd process

[0641]Except that the compound represented by the above formula (30) was used instead of the compound represented by the above formula (20) used in ...

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Abstract

The present invention relates to a photochromic compound including an indenonaphthopyran skeleton, wherein the indenonaphthopyran skeleton includes a C10-30 alkenyl group and an oligomer chain group Acomprising three or more repeating units selected from among a polyalkylene oxide oligomer chain group, a polyester oligomer chain group, a polysiloxane chain group, and a polyester polyether oligomer chain group. The present invention can provide a photochromic compound which exhibits excellent photochromic properties in various cured objects and can inhibit the cured objects from being opaque.

Description

technical field [0001] The present invention relates to a novel photochromic compound, a novel photochromic curable composition and an optical article comprising the photochromic compound. Background technique [0002] Photochromic compounds represented by chromene compounds, fulgid anhydride compounds, spirooxazine compounds, etc. have the following characteristics (photochromic properties): when irradiated with light containing ultraviolet rays such as sunlight or mercury lamp light, the It changes color quickly, and returns to its original color when it is placed in a dark place after stopping light irradiation. This characteristic is effectively utilized, and it has been used in various applications, especially optical materials. [0003] For example, a photochromic spectacle lens provided with photochromic properties through the use of a photochromic compound is rapidly colored and functions as sunglasses outdoors exposed to light such as sunlight that includes ultravio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C08G65/332C08G77/14C08G77/38C08L83/06C08L101/00
CPCC08G65/332C08G77/38C08G77/14C08L83/06C09K9/02C08L101/00C08K5/1545C08K5/16C08L75/04C08L77/06C08G18/24C08G18/3225G02B1/04G02B1/18C09K2211/1003C09K2211/1088C08G18/722
Inventor 宫崎真行竹中润治
Owner TOKUYAMA CORP
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