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Chromene compound and photochromic optical article

A technology of chromene compounds and polymerizable groups, which is applied in the field of new photochromic optical articles, can solve problems such as adverse effects on the eyes, achieve high degree of polymerization, and inhibit dissolution

Pending Publication Date: 2022-02-15
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In particular, when forming a contact lens, there is a problem with the elution of photochromic compounds in that it causes adverse effects on the eyes due to elution and diffusion into the eye.

Method used

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  • Chromene compound and photochromic optical article
  • Chromene compound and photochromic optical article
  • Chromene compound and photochromic optical article

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0308] 1.0 g (2.8 mmol) of the naphthol compound represented by the following formula (19)

[0309]

[0310] 10 mass % methyl ethyl ketone solution 12.0 g (3.4 mmol) of a propargyl alcohol compound having a reactive substituent (hydroxyl group) represented by the following formula (20)

[0311]

[0312] This was dissolved in 50 mL of toluene, 0.02 g of p-toluenesulfonic acid was further added, and the mixture was stirred under heating and reflux for 1 hour. After the reaction, the solvent was removed, and purification was performed by silica gel chromatography to obtain 1.4 g of a white powdery product (precursor). The yield was 72%.

[0313] The obtained precursor was dissolved in 0.7 g (6.9 mmol) of triethylamine and 30 mL of dichloromethane, and ice-cooled. There, 0.3 g (2.9 mmol) of acryloyl chloride was slowly added dropwise. After the reaction, the solvent was removed, and purification was performed by silica gel chromatography to obtain 1.3 g of a white powdery...

Embodiment 2～10

[0319] In the same manner as in Example 1, the chromene precursors and chromene compounds shown in Tables 4 to 6 were synthesized using the naphthol compounds shown in Tables 1 to 3 and the propargyl alcohol compound having a reactive substituent. As a result of structural analysis of the obtained product using the same structure confirmation method as in Example 1, it was confirmed that it was a compound represented by the structural formulas shown in Tables 4-6. In addition, Table 7 shows the elemental analysis values ​​of these compounds, the calculated values ​​obtained from the structural formulas of each compound, and 1 Characteristic spectrum of H-NMR spectrum.

[0320] [Table 1]

[0321]

[0322] [Table 2]

[0323]

[0324] [table 3]

[0325]

[0326] [Table 4]

[0327]

[0328] [table 5]

[0329]

[0330] [Table 6]

[0331]

[0332] [Table 7]

[0333]

Embodiment 11～22

[0335] (Physical property evaluation of produced photochromic contact lenses (photochromic optical articles))

[0336] As the photochromic curable composition, tris(trimethylsiloxy)silylpropyl methacrylate / dimethylacrylamide / 2-hydroxyethyl methacrylate as radical polymerizable monomers were used / Ethylene glycol dimethacrylate in the compounding ratio of 60 parts by mass / 30 parts by mass / 8 parts by mass / 2 parts by mass, respectively. With respect to 100 parts by mass of the mixture of radically polymerizable monomers, 1 part by mass of chromene compounds Nos. 1 to 10 obtained in Examples 1 to 10 was added and mixed well, and then 0.3 parts by mass of thermal polymerization initiator V65 was added. (2,2'-azobis(2,4-dimethylvaleronitrile)) and fully mixed to prepare a photochromic curable composition. The obtained photochromic curable composition was injected into a mold composed of a glass plate and a polyethylene terephthalate (PTFE) sheet having a film thickness of 0.1 mm, a...

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Abstract

The present invention provides a chromene compound which can exhibit excellent photochromic properties. The chromene compound of the present invention is represented by formula (1). In the formula, at least one of R1 and R2 represents a group having a radical-polymerizable group, wherein the group having a radical-polymerizable group is represented by formula (2) (wherein R10 represents a linear or branched alkylene group having 1 to 10 carbon atoms, and l represents an integer of 0 to 50); and the ring Z that is represented by formula (Z) and is spiro-bonded to a carbon atom located at position-13 in formula (1) is preferably an aliphatic cyclic group in which the number of carbon atoms that constitute the ring in conjunction with the carbon atom located at the position-13 is 3 to 20 and which may have a substituent, or the like.

Description

technical field [0001] The present invention relates to a novel chromene compound with a polymerizable group, and a novel photochromic optical article obtained by polymerizing the chromene compound. Background technique [0002] Photochromism is a reversible reaction in which the color of a compound changes rapidly when it is irradiated with ultraviolet light such as sunlight or light from a mercury lamp, and when the light is stopped and placed in a dark place, it returns to its original color due to heat. . Photochromic compounds having this property are used in applications where reversible discoloration or darkening induced by sunlight is desired, for example as materials for photochromic spectacle lenses and photochromic contact lenses. [0003] In photochromic compounds used in plastic spectacle lenses, in general, the following characteristics are required. [0004] (1) The degree of coloration in the visible light region (hereinafter, referred to as initial colorat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/96C08F230/08C08F220/54C08F220/20C08F222/14C08F220/36C08F220/30C09K9/02G02C7/10
CPCC07D311/96C09K9/02C08F230/085G02C7/102C09K2211/1088C08F220/54C08F220/20C08F222/102C08F220/36C08F220/302C07D311/78C09K2211/1007C07D311/94C07D513/22C07D327/06C09D4/00C08L33/14G02B1/043C08L2666/70C08L75/04C08L81/00C08F220/56C08F222/1063C08F222/103C08F220/325C09K2211/1018G02C7/04
Inventor 宫崎真行竹中润治百田润二
Owner TOKUYAMA CORP
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