Photochromic compound and curable composition comprising same
A photochromic and compound technology, applied in the direction of silicon organic compounds, color-changing fluorescent materials, compounds of elements of Group 4/14 of the periodic table, etc., can solve the problems of low photochromic durability and no research on temperature dependence. , to achieve the effect of stable color tone, reduced temperature dependence, and color maintenance
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Embodiment 1
[0428] The first process:
[0429] Make 2.68g (10.0mmol) of 4,4'-stilbene dicarboxylic acid
[0431] DMF 3 drops
[0432] Reflux for 2 hours under nitrogen. After confirming the consumption of the raw material, it was concentrated under reduced pressure and dried to obtain 4,4'-stilbene dicarboxylic acid chloride as a yellow solid in a yield of 100%.
[0433] The second process:
[0434] In the 4,4'-stilbene dicarboxylic acid chloride obtained in the first step, add
[0435] Aluminum chloride 2.93g (22.0mmol)
[0436] Dichloromethane 30mL,
[0437] Stir under nitrogen for 1 hour.
[0438] Anisole 2.70g (25.0mmol)
[0439] Dichloromethane 50mL
[0440] After stirring under ice-cooling, the dichloromethane solution of 4,4'-stilbene dicarboxylic acid chloride and ammonium chloride obtained above was added thereto, and stirred for 12 hours while raising the temperature to room temperature.
[0441] 500 mL of methanol was added under ice-coo...
Embodiment 2～4
[0471] In the same manner as in Example 1, propargyl alcohol compounds shown in Table 1 (Examples 2 to 4) were prepared, and the naphthol compound in Example 1 was reacted to synthesize chromene compounds (photochromic compounds).
[0472] [Table 1]
[0473]
[0474] As a result of structural analysis of the obtained chromene compound using the same structure confirmation means as in Example 1, it was confirmed that it was a compound represented by the structural formula shown in Table 1.
[0475] In addition, Table 2 shows the elemental analysis values of these compounds, the calculated values obtained from the structural formulas of the respective compounds, and 1 Characteristic spectra of H-NMR spectra.
[0476] [Table 2]
[0477]
Embodiment 5～8
[0479] (Evaluation in toluene solution)
[0480] 0.05 mmol / L (0.1 mmol / L in terms of photochromic site conversion) toluene solutions of the photochromic compounds of Examples 1 to 4 were prepared, and the following evaluations were performed using a quartz cuvette with an optical path length of 1 cm. The results are shown in Table 3.
[0481] (1) Photochromic properties
[0482] [1] Maximum absorption wavelength (λmax):
[0483] The maximum absorption wavelength after color development was determined by a spectrophotometer (instantaneous multi-channel photodetector MCPD3000) manufactured by Otsuka Denshi Kogyo Co., Ltd., and was used as an index of color tone during color development.
[0484] [2] Color concentration at 23°C (A 23 ):
[0485] It is the difference between the absorbance {ε(180)} after light irradiation at 23°C for 180 seconds at the maximum absorption wavelength and the absorbance ε(0) without light irradiation, and is used as an index of color density. It...
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