JPH08157467A - Chromene compounds and photochromic materials - Google Patents

Abstract

(57) [Summary] (Modified) [Structure] A chromene represented by the general formula (1) having a naphthyl group and a phenyl group at the 3-position and having a basic structure in which a benzene ring is condensed at the f-position. A compound and its derivative, and a photochromic material comprising them. [Wherein R ¹ and R ² are a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, an acyl group, a cyano group, an amino group, an acyloxy group, a benzoyloxy group or a halogen atom, and R ³ and R ⁴ and R ⁵ are hydrogen atom, alkyl group, alkoxy group, aryl group, aralkyl group, halogen atom, cyano group or hydroxy group, and n, a, b and c are integers of 1 or 2. [Effect] The chromene compound of the formula (1) has excellent photochromic properties, and has characteristics of a deep color density and a fast fading speed.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention changes to a form colored or darkened by light containing ultraviolet rays such as sunlight or light from a mercury lamp, the change being reversible, having a deep color density and being colorless. The present invention relates to a novel chromene compound exhibiting a property of rapidly returning to a state (hereinafter, referred to as fading speed).

[0002]

2. Description of the Related Art Photochromism is a phenomenon that has been attracting attention for several years, and when a compound is irradiated with light including ultraviolet rays such as sunlight or the light of a mercury lamp, the color of the compound is rapidly changed and the irradiation of light occurs. It is a reversible action that returns to the original color when stopped and left in the dark. A compound having this property is called a photochromic compound, and various compounds have been synthesized conventionally, but no special commonality is recognized in the structure.

US Pat. No. 3,567,605 describes a chromene compound represented by the following formula.

[0004]

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This chromene compound is around room temperature (20-3
Although it exhibits photochromic properties at 0 ° C.), the color density upon irradiation with ultraviolet rays is low and not practical.

[0006] USP9300873 discloses a chromene compound represented by the following formula.

[0007]

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Although this compound had an increased color density as compared with the compound described in USP 3567605, it had a slow fading rate and was not practically satisfactory.

[0009]

DISCLOSURE OF THE INVENTION The inventors of the present invention have conducted earnest studies to obtain a photochromic compound having excellent color developability near room temperature and a high fading rate.

[0010]

As a result, they have succeeded in synthesizing a novel chromene compound, and have found that the chromene compound has excellent color developability at around room temperature and above room temperature, and exhibits a property of fading speed. , To complete the present invention.

That is, the present invention has the general formula (1)

[0012]

[Chemical 4]

(Wherein R ¹ and R ² are the same or different hydrogen atoms, alkyl groups, alkoxy groups, aryl groups,
An aralkyl group, an acyl group, a cyano group, an amino group, an acyloxy group, a benzoyloxy group or a halogen atom,
R ³ , R ⁴ and R ⁵ are the same or different hydrogen atoms, alkyl groups, alkoxy groups, aryl groups, aralkyl groups,
A halogen atom, a cyano group or a hydroxy group,
n, a, b and c represent the numbers of the respective substituents and are integers of 1 or 2, respectively. ) Is a chromene compound.

Another invention is a photochromic material comprising the above chromene compound.

In the above general formula (1), R ¹ and R ² are the same or different hydrogen atoms, alkyl groups, alkoxy groups,
It is an aryl group, aralkyl group, acyl group, cyano group, amino group, acyloxy group, benzoyloxy group or halogen atom.

The alkyl group and alkoxy group in the general formula (1) are not particularly limited, but generally have 1 to 10 carbon atoms,
It is preferably 1 to 4. Specific examples of this alkyl group include a methyl group, an ethyl group, an isopropyl group, and the like. Examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropyloxy group, and the like, and the aryl group has 6 to 10 carbon atoms. It is preferably 10 and specifically exemplified are a phenyl group, a naphthyl group and the like, and the aralkyl group preferably has 7 to 14 carbon atoms, and specifically, a benzyl group, a phenylethyl group and a naphthyl group. Examples thereof include a methyl group. The acyl group is not particularly limited, but generally has 2 to 10 carbon atoms, preferably 2 to 7 carbon atoms. Specific examples of this acyl group include an acetyl group, a propionyl group, and a benzoyl group.

The amino group in the general formula (1) is not particularly limited, but preferably the following general formula

[0018]

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[Wherein R ⁸ and R ⁹ are groups represented by the same or different hydrogen atom, alkyl group, aryl group or aralkyl group, or

[0020]

[Chemical 6]

{Wherein R ¹⁰ and R ¹¹ are the same or different alkylene groups, and X is an oxygen atom, a sulfur atom or the following formula:

[0022]

[Chemical 7]

(Wherein R ¹² is an alkyl group). }] Is used.

The alkyl group represented by R ⁸ , R ⁹ and R ¹² in the above general formula is not particularly limited, but generally has 1 to 20 carbon atoms, preferably 1 to 4 carbon atoms. Is. Specifically, a methyl group, an ethyl group, a propyl group, a butyl group, or the like can be given. The aryl group preferably has 6 to 10 carbon atoms, and specifically,
Examples thereof include a phenyl group and a naphthyl group. The aralkyl group preferably has 7 to 14 carbon atoms, and specific examples thereof include a benzyl group, a phenylethyl group, a phenylpropyl group and a naphthylmethyl group.

The alkylene group represented by R ¹⁰ and R ¹¹ is not particularly limited, but generally has 1 to 10 carbon atoms.
It is suitable that it is 4, preferably 1-2. Specific examples thereof include a methylene group and an ethylene group.

Specific examples of suitable amino groups in the general formula (1) include methylamino group, ethylamino group, propylamino group, butylamino group, isopropylamino group, dimethylamino group, diethylamino group, dipropyl group. Amino group, dibutylamino group, methylethylamino group,
Ethylpropylamino group methylbutylamino group, phenylethylamino group, phenylmethylamino group, diphenylamino group, phenylnaphthylamino group, benzylmethylamino group, benzylethylamino group, phenylbenzylamino group, dibenzylamino group, naphthylmethyl group Examples thereof include ethylamino group, piperidino group, pyrrolidino group, piperazino group, methylpiperazino group, morpholino group, thiomorpholino group, aziridino group, thiazolidino group and indolino group. Among them, a piperidino group, a piperazino group, a methylpiperazino group or a morpholino group is particularly preferable. The acyloxy group in the general formula (1) is not particularly limited, but generally has 2 to 10 carbon atoms, preferably 2 carbon atoms.
It is suitable that it is -5. Specific examples thereof include an acetoxy group and a propoxy group. Examples of the halogen atom include fluorine, chlorine, bromine and the like.

In the general formula (1), n represents the number of substituents R ¹ and is an integer of 1 or 2.

The substitution positions of the substituents R ¹ and R ² are not particularly limited, but R ¹ is at the 8 or 9 position in the general formula (1),
R ² is preferably a compound located at the 6-position in the general formula (1) since the color density is high.

In the general formula (1), R ³ , R ⁴ and R ⁵
Are the same or different hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkoxy groups, halogen atoms, cyano groups or hydroxy groups.

The alkyl group and alkoxy group are not particularly limited, but generally have 1 to 10 carbon atoms, preferably 1 carbon atoms.
It is preferable that it is ~ 4. Specific examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, and the like, and the alkoxy group includes a methoxy group, an ethoxy group, and an isopropyloxy group. The aryl group preferably has 6 to 10 carbon atoms, and specific examples thereof include a phenyl group and a naphthyl group, and the aralkyl group preferably has 7 to 14 carbon atoms. Specific examples thereof include a benzyl group, a phenylethyl group, a phenylpropyl group and a naphthylmethyl group. Examples of the halogen atom include fluorine, chlorine, bromine and the like.

In the general formula (1), a represents the number of substituents R ³ , b represents the number of substituents R ⁴ , and c represents the number of substituents R ⁵ , each of which is an integer of 1 or 2. .

The substitution positions of the substituents R ³ , R ⁴ and R ⁵ are not particularly limited, but R ³ is at the o or p position of the phenyl group in the general formula (1), and R ⁴ is 1 or 3 of the naphthyl group. The compound substituted at the position is preferred because of its high color density.

Specific examples of the preferred chromene compound in the present invention include the following compounds.

1) 3- (2-naphthyl) -3-phenyl-3H-benzo (f) chromene 2) 8-methoxy-3- (2-naphthyl) -3-phenyl-3H-benzo (f) chromene 3 ) 9-Methoxy-3- (2-naphthyl) -3-phenyl-3H-benzo (f) chromene 4) 8-benzoyl-3- (2-naphthyl) -3-phenyl-3H-benzo (f) chromene 5 ) 8-Cyano-3- (2-naphthyl) -3-phenyl-3H-benzo (f) chromene 6) 8-ethoxy-6-piperazino-3- (2-naphthyl) -3-phenyl-3H-benzo ( f) chromene 7) 7-ethyl-9-phenyl-3- (2- (1-methylnaphthyl))-3-phenyl-3H-benzo (f) chromene 8) 8-acetyl-3- (2- (1 -Fluoronaphthyl))-3- ( 4-Methylphenyl) -2H-benzo (f) chromene 9) 8-isopropoxy-6-morpholino-3- (2-
(3-Chloro-6-ethylnaphthyl))-3-phenyl-3H-benzo (f) chromene 10) 8-benzoyloxy-9-bromo-3- (2-
(7-Bromo-4-ethoxynaphthyl))-3- (2-
Chlorophenyl) -3H-benzo (f) chromene The compound represented by the above general formula (1) of the present invention generally exists as a colorless or pale yellow solid or viscous liquid at room temperature under normal pressure. ) ~ (C) can be confirmed.

(A) Proton nuclear magnetic resonance spectrum ( ¹
The type and number of protons present in the molecule can be known by measuring (H-NMR).

That is, a peak due to an aromatic proton near δ 6.5 to 9 ppm, δ 3 to 4.5 p
a peak based on a proton of carbon bonded to nitrogen near pm, a peak based on a proton of carbon bonded to carbonyl near δ2.5 to 4 ppm and a peak based on a proton of carbon bonded to oxygen near δ3.5 to 4 ppm, δ
A peak based on the proton of the alkyl group appears around 1.2 to 2.5 ppm. Further, the number of protons of each bonding group can be known by relatively comparing the respective δ peak intensities.

(B) For elemental analysis, the respective weight percentages of carbon, hydrogen, nitrogen, sulfur and halogen can be determined. Furthermore, the weight% of oxygen can be calculated by subtracting the total weight% of the recognized elements from 100. Therefore, the composition of the corresponding product can be determined.

(C) ¹³ C-nuclear magnetic resonance spectrum ( ¹³ C
It is possible to know the type of carbon present in the molecule by measuring -NMR).

That is, a peak due to carbon of an alkyl group is present at about δ15 to 40 ppm, a peak due to carbon of an aromatic hydrocarbon and an aromatic carbon bound to oxygen is present at about δ110 to 160 ppm, and oxygen is present at about δ80 to 100 ppm. Peak due to bound quaternary carbon, δ55-75p
A peak of secondary carbon bonded to oxygen appears near pm.

The method for producing the compound represented by the general formula (1) of the present invention is not particularly limited and may be obtained by any synthetic method. A typical method that is generally adopted is described below.

A compound represented by the following general formula (2):

[0042]

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{However, R ¹ , R ² and n have the same meaning as in the general formula (1). } The compound represented by the following general formula (3):

[0044]

[Chemical 9]

{However, R ³ , R ⁴ , R ⁵ , a, b and c
Is synonymous with the general formula (1). } A chromene compound is obtained by the method of reacting under an acid catalyst.

The reaction of the compound represented by the general formula (2) with the compound represented by the general formula (3) is typically performed as follows.

The reaction ratio of these two compounds is selected from a wide range, but is generally selected from the range of 1:10 to 10: 1 (molar ratio). Examples of the acid catalyst include sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid, and the like, and the addition amount is 100 weight% of the compound of the general formula (2) and the compound of the general formula (3). It is 0.1 to 10 parts by weight with respect to parts. The reaction temperature is usually 0 to 200 ° C., and an aprotic solvent such as toluene, benzene or tetrahydrofuran is used as the solvent. The chromene compound represented by the above general formula (1) of the present invention is well soluble in general organic solvents such as toluene, chloroform and tetrahydrofuran. When the chromene compound represented by the general formula (1) is dissolved in such a solvent, it is colorless and transparent, and when it is irradiated with sunlight or ultraviolet rays, it rapidly changes into a colored or dark color,
It exhibits a good reversible photochromic effect that quickly returns to its original colorless state when light is blocked. The photochromic action of the compound represented by the general formula (1) exhibits similar characteristics even in the polymer solid matrix.

The target polymer solid matrix may be one in which the chromene compound represented by the general formula (1) of the present invention is uniformly dispersed. Optically preferably, for example, polymethyl acrylate or polyacrylate is used. Thermoplastic resins such as ethyl acrylate, polymethylmethacrylate, polyethylmethacrylate, polystyrene, polyacrylonitrile, polyvinylalcohol, polyacrylamide, poly (2-hydroxyethylmethacrylate), polydimethylsiloxane, and polycarbonate can be mentioned. .

Further, ethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, ethylene glycol bisglycidyl methacrylate, bisphenol A dimethacrylate, 2,2-bis (4-methacryloyloxyethoxyphenyl). Polyvalent acrylic acid and polymethacrylic acid ester compounds such as propane and 2,2-bis (3,5-dibromo-4-methacryloyloxyethoxyphenyl) propane; diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl tartrate, epoxy Diallyl succinate, diallyl fumarate, diallyl chlorendate, diallyl hexaphthalate, diallyl carbonate, allyl dig Call carbonate, polyvalent allyl compounds such as trimethylolpropane triallyl carbonate; 1,2-bis (methacryloyl thio) ethane,
Bis (2-acryloylthioethyl) ether, 1,4
-Polyvalent thioacrylic acid and polyvalent thiomethacrylic acid ester such as bis (methacryloylthiomethyl) benzene; glycidyl acrylate, glycidyl methacrylate, β
-Methylglycidyl methacrylate, bisphenol A
-Monoglycidyl ether-methacrylate, 4-glycidyloxymethacrylate, 3- (glycidyl-2-
Oxyethoxy) -2-hydroxypropyl methacrylate, 3- (glycidyloxy-1-isopropyloxy) -2-hydroxypropyl acrylate, 3- (glycidyloxy-2-hydroxypropyloxy) -2
-Hydroxypropyl acrylate and other methacrylate compounds or acrylate compounds; and thermosetting resins obtained by polymerizing radically polymerizable polyfunctional monomers such as divinylbenzene.

Further, these monomers and unsaturated carboxylic acids such as acrylic acid, methacrylic acid and maleic anhydride; methyl acrylate, methyl methacrylate, benzyl methacrylate, phenyl methacrylate, 2-hydroxyethyl methacrylate, etc. Acrylic acid and methacrylic acid ester compounds; diethyl fumarate, diphenyl fumarate, and other fumaric acid ester compounds; methylthioacrylate, benzylthioacrylate, benzylthiomethacrylate, and other thioacrylic acid and thiomethacrylic acid ester compounds; styrene, chlorostyrene, Examples thereof include copolymers with radically polymerizable monofunctional monomers such as vinyl compounds such as methylstyrene, vinylnaphthalene, α-methylstyrene dimer and bromostyrene.

Further, addition copolymerization of a polyvalent thiol compound such as ethanedithiol, propanetriol, hexanedithiol, pentaerythritol tetrakisthioglycolate and di (2-mercaptoethyl) ether with the above radical-polymerizable polyfunctional monomer. Polymer: diphenylethane diisocyanate, xylylene diisocyanate, p
An addition polymer of a polyvalent isocyanate compound such as phenylene diisocyanate and a polyhydric alcohol compound such as ethylene glycol, trimethylolpropane, pentaerythritol and bisphenol A, or the above-mentioned polyvalent thiol compound can be used. These raw material monomers are 1
It is possible to use one kind or a mixture of two or more kinds.

The method for dispersing the chromene compound represented by the general formula (1) of the present invention in the polymer solid matrix is not particularly limited, and a general method can be used. For example, a method in which the thermoplastic resin and the chromene compound are kneaded in a molten state and dispersed in the resin or after the chromene compound is dissolved in the polymerizable polyfunctional monomer, and then a polymerization catalyst is added thereto by heat or light. Examples thereof include a method of polymerizing and dispersing in a resin, and a method of dispersing in a resin by dyeing the surface of the thermoplastic resin or the thermosetting resin with a chromene compound.

The chromene compound of the present invention can be widely used as a photochromic agent. For example, various recording materials, copying materials, printing photoconductors, cathode ray tube recording materials, laser light-sensitive materials, holography can be used instead of silver salt sensitizers. It is used as various recording materials such as light-sensitive materials for automobiles. In addition, the photochromic material using the chromene compound of the present invention can also be used as a material for a photochromic lens material, an optical filter material, a display material, a photometer, a decoration and the like. For example, when used for a photochromic lens, it is not particularly limited as long as it is a method capable of obtaining uniform light control performance, and if specifically exemplified, a polymer film obtained by uniformly dispersing the photochromic material of the present invention. Is sandwiched around the lens center, or the chromene compound and the heat or photopolymerization initiator are dissolved in a polymerizable monomer and then cured by a predetermined method, or the chromene compound is dissolved in, for example, silicone oil. And the surface of the lens is impregnated at 150 to 200 ° C. for 10 to 60 minutes, and the surface is coated with a curable substance to form a photochromic lens. Further, a method in which the polymer film is applied to the lens surface and the surface is coated with a curable substance to form a photochromic lens can be considered.

In the present invention, a chromene compound represented by the following general formula is a particularly preferred chromene compound from the viewpoints of color density, easiness of synthesis and the like.

[0055]

[Chemical 10]

(However, R ¹ is a hydrogen atom, an alkyl group and an alkoxy group, R ² is a hydrogen atom and an amino group, and R ³ and R ⁴ are a hydrogen atom, an alkyl group, an alkoxy group and a fluorine atom. .)

[0057]

INDUSTRIAL APPLICABILITY The chromene compound of the present invention, when uniformly dispersed in a solution or a polymer, is around room temperature (20 to 3).
Not only at 0 ° C. but also at a temperature higher than room temperature (30 to 40 ° C.), a deep color density is exhibited, and a further fading speed is exhibited. For example, a photochromic lens using the chromene compound of the present invention gives an excellent light-shielding property because it develops a deep color when placed outdoors, and when it returns to a dark room, the color fades rapidly, so that the visual field is not blocked. Absent.

[0058]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. In addition, "part" in an Example is a "weight part."

Example 1 2.88 g (0.02 mol) of the following compound,

[0060]

[Chemical 11]

5.48 g (0.02 mol) of the following compound
When,

[0062]

[Chemical 12]

P-toluenesulfonic acid 0.0836 g
(0.00044 mol) was dissolved in 150 ml of toluene and heated under reflux for 2 hours. After the reaction, the solvent was removed, and the product was purified by chromatography on silica gel to give 3.07 g (0.008 m) of a product of slightly yellow crystals.
ol) was obtained. The yield was 40%.

The elemental analysis value of this product is C90.54.
%, H5.26%, O4.20%, C29H20O
Calculated value corresponding to 1 is C90.6%, H5.24
%, O 4.16%. Moreover, when the proton nuclear magnetic resonance spectrum was measured, δ 6.5
2 based on aromatic protons around 9.0 ppm
Peak at 0H (Figure 1). Moreover, when ¹³ C-NMR was measured, a naphthalene ring was found around δ 110 to 160 ppm.
A peak due to the carbons at the 3 and 4 positions of the benzene ring and chromene and a peak due to the 2 position of the chromene were shown at around δ80 ppm.

From the above results, it was confirmed that the isolated product was a compound represented by the following structural formula (5).

[0066]

[Chemical 13]

Example 2 2.88 g (0.02 mol) of the following compound,

[0068]

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5.48 g (0.02 mol) of the following compound
When,

[0070]

[Chemical 15]

0.0836 g of sulfuric acid (0.00085 mo
l) was dissolved in 100 ml of toluene and refluxed for 2 hours.
After the reaction, the solvent was removed and the product was purified by chromatography on silica gel to give a pale yellow crystalline product.
9 g (0.007 mol) was obtained. The yield was 35%.

The elemental analysis value of this product is C86.90.
%, H5.36%, O7.74%, C30H22O
Calculated value corresponding to 2 C86.93%, H5.35
% And O7.72%. Moreover, when the proton nuclear magnetic resonance spectrum was measured, δ 6.5
1 based on aromatic protons around 9.0 ppm
A peak of 9H and a peak of 3H based on the proton of the methoxy group were shown in the vicinity of δ 3.5 to 5.5 ppm. Also, ¹³
When C-NMR was measured, δ 110-160 ppm
Near the naphthalene ring, benzene ring and chromene 3,
A peak based on the carbon at the 4-position, a peak based on the 2-position of chromene near δ80 ppm, and a peak based on the carbon of the methoxy group near δ70 ppm were shown.

From the above results, it was confirmed that the isolated product was a compound represented by the following structural formula (6).

[0074]

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Examples 3 to 34 The chromene compounds shown in Table 1 were synthesized in the same manner as in Examples 1 and 2. The obtained product was subjected to structural analysis by the same means for confirming structure as in Example 1, and as a result, it was confirmed to be a compound represented by the structural formula shown in Table 1.

Table 2 shows the elemental analysis values of this compound and the calculated values obtained from the structural formula of each compound. Also,
The numerical value of the obtained proton nuclear magnetic resonance spectrum is also shown.

[0077]

[Table 1]

[0078]

[Table 2]

[0079]

[Table 3]

[0080]

[Table 4]

[0081]

[Table 5]

[0082]

[Table 6]

[0083]

[Table 7]

[0084]

[Table 8]

[0085]

[Table 9]

[0086]

[Table 10]

[0087]

[Table 11]

[0088]

[Table 12]

[0089]

[Table 13]

[0090]

[Table 14]

Example 35 0.1 part of the chromene compound obtained in Example 1, 70 parts of tetraethylene glycol dimethacrylate, 15 parts of triethylene glycol dimethacrylate, 10 parts of glycidyl methacrylate, 5 parts of 2-hydroethyl methacrylate, 1 part of perbutyl ND was added as a polymerization catalyst, and they were mixed sufficiently until they were completely dissolved. This mixed solution was poured into a mold composed of a glass plate and a gasket composed of an ethylene-vinyl acetate copolymer, and the mixture was blown with an air oven at 35
Polymerization was carried out by raising the temperature from ℃ to 90 ℃ over 20 hours. After completion of the polymerization, the polymer was removed from the glass mold of the mold.

To the obtained polymer (thickness: 2 mm), a xenon lamp L-2480 (300 W) manufactured by Hamamatsu Photonics was used.
SHL-100 was passed through an aeromass filter (manufactured by Corning) at 20 ° C. ± 1 ° C., the beam intensity on the polymer surface was 365 nm = 2.4 mW / cm 2, 245 nm = 24 μm.
It was irradiated with W / cm2 for 120 seconds to develop a color, and the photochromic property was measured. The photochromic properties were expressed as follows. The results are shown in Table 3.

Maximum absorption wavelength (λMAX): From a spectrophotometer (instantaneous multi-channel photo detector MCPD1000) manufactured by Otsuka Electronics Co., Ltd.,
ΛMAX before and after color development of this polymer was determined.

Ε (120 seconds): At the maximum absorption wavelength,
Absorbance of this polymer after irradiation for 120 seconds under the above conditions.

Ε (0 sec): Absorbance of unirradiated polymer at the same wavelength as the maximum absorption wavelength when irradiated with light.

Ε (120 sec) -ε (0 sec): Color density Half-life t 1/2: After irradiation for 120 sec, the absorbance of this polymer is 1 of [ε (120 sec) -ε (0 sec)]. The time required to drop to / 2.

Examples 36 to 68 As chromene compounds in Example 35,
Example 35 was repeated except that the chromene compound obtained in 34 was used. The results are shown in Table 3.

Comparative Examples 1 and 2 Further, for comparison, the photochromic properties of two kinds of chromene compounds represented by the following formulas were measured by the same method as in Example 35. The results are shown in Table 3.

[0099]

[Chemical 17]

[0100]

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[0101]

[Table 15]

[0102]

[Table 16]

The compound of the present invention has a color density higher than that of the compound of Comparative Example 1 by a factor of 2 or more, a faster fading rate than the compound of Comparative Example 2, and is excellent in color density and fading rate.

[Brief description of drawings]

FIG. 1 is a proton nuclear magnetic resonance spectrum of the compound obtained in Example 1 of the present invention.

Claims (2)

[Claims] 1. The following general formula (1): (However, R ¹ and R ² are the same or different hydrogen atoms,
An alkyl group, an alkoxy group, an aryl group, an aralkyl group, an acyl group, a cyano group, an amino group, an acyloxy group, a benzoyloxy group or a halogen atom, and R ³ , R ⁴ and R ⁵ are the same or different hydrogen atoms, alkyl Base,
It is an alkoxy group, an aryl group, an aralkyl group, a halogen atom, a cyano group or a hydroxy group, and n, a, b and c represent the numbers of the respective substituents and each is an integer of 1 or 2. ) A chromene compound represented by. 2. A photochromic material comprising the chromene compound according to claim 1.