JPH0812677A - Imonobutylolactam-based compound, its production and photochromic material containing the same compound - Google Patents

Abstract

PURPOSE:To obtain a new compound capable of providing a photochromic material excellent in image stability, heat resistance, weather resistance and repeated durability, exhibiting bright coloring and useful for optical recording materials, display materials. decoration, etc. CONSTITUTION:This compound is expressed by formula I [(A) is a monovalent (substituted)aromatic group; at least one among R2 to R4 is a (substituted) aromatic heterocyclic residue and the residual groups and R1 are each an alkyl, an aralkyl or aryl or two groups in combination not having a (substituted) aromatic heterocyclic residue in the combination of R1 and R2, and R3 and R4 together form a cycloalkylidene groupl, e.g. E-iminolactam compound of formula II or 2-iminolactam compound of formula III. The compound is obtained by reacting, e.g. fulgides with an aromatic diamine without or in an inert solvent, especially preferably at 80 to 120 deg.C under reduced pressure, as necessary, using a dehydrating agent.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an iminobutyrolactam compound useful as a photochromic material and a method for producing the same, more specifically, a novel iminobutyrolactam which can be used as an optical recording material, a display material, a decoration and the like. The present invention relates to a system compound and a photochromic material containing the compound.

[0002]

2. Description of the Related Art Light causes a reversible structural change,
A photochromic compound whose visible absorption spectrum changes with it has been actively studied for application to rewritable optical recording media and optical elements such as holograms.

Known photochromic compounds are spiropyran compounds, spirooxazine compounds, diarylethene compounds, fulgide compounds, and the like. Among these, fulgide compounds are colorless from a color former (closed ring) due to heat. It has been widely studied because of its characteristics such as a slow isomerization reaction rate to the body (ring-opened body) and excellent record keeping in the dark.

[0004]

However, the conventionally known fulgide compounds cannot be said to have sufficient durability against repeated coloring-decoloring, and when regarded as a coloring material, the coloring hue is extremely high. There was only a limited number.

Further, as a means for increasing the wavelength of absorption of fulgide compounds, it is known to introduce an aromatic nitrogen-containing heterocyclic structure into the part involved in the pericyclic reaction.
Since aromatic nitrogen-containing heterocyclic compounds are highly reactive,
Since the side reaction is likely to occur in the synthetic process, the yield of the target fulgide compound is low, and the weather resistance of the target product is slightly inferior to other fulgide compounds having an aromatic heterocyclic structure. was there.

The problem to be solved by the present invention is that the photochromic material is excellent in image stability, heat resistance, weather resistance and repetitive durability, exhibits clear color development, and is useful for optical recording materials, display materials, decorations and the like. To provide.

[0007]

Means for Solving the Problems The inventors of the present invention have conducted extensive studies to solve these problems, and as a result, the general formula (I)

[0008]

Embedded image

(In the formula, [A] represents a divalent aromatic group which may have a substituent, and among R ₂ , R ₃ and R ₄ ,
At least one group represents an aromatic heterocyclic residue which may have a substituent, and the remaining two groups and R ₁ are each independently an alkyl group, an aralkyl group or an aryl group, or R ₁ and R _{1. Two} groups of the combination of _{2 and} the combination of R ₃ and R ₄ which does not have an aromatic heterocyclic residue which may have a substituent are linked to each other to represent a cycloalkylidene group. The present invention has been completed by finding that a group of compounds represented by (4) shows a photochromism of clear color development, has a considerably long absorption wavelength, and is excellent in repeated durability.

That is, in order to solve the above problems, the present invention solves the above-mentioned problems by iminobutyrolactam compounds represented by the above general formula (I) (hereinafter referred to as photochromic compounds of the present invention) and photochromic materials containing the compounds. I will provide a.

The photochromic compound of the present invention can be synthesized by using a conventionally known appropriate reaction means. For example, a method of synthesizing fulgides with an aromatic diamine, a precursor of fulgides 2 The method of synthesizing by reacting a 3,3-bisalkylidene succinic acid derivative and an aromatic diamine can be mentioned. The photochromic compound of the present invention thus obtained can be purified and isolated by means of column chromatography, recrystallization and the like. The above reaction can be carried out in a suitable inert organic solvent, or can be carried out without solvent. The reaction temperature is preferably in the range of 50 to 150 ° C., and 80 to 1
The range of 20 ° C. is particularly preferred. It is also possible to accelerate the removal of water produced by the reaction by reducing the pressure so that the reaction raw materials, products, solvents, etc. do not volatilize. For removing water, it is effective to use a dehydrating agent such as an acid anhydride, an acid halide, an inorganic oxide or an inorganic halide.

As the fulgides used in the synthesis of the photochromic compound of the present invention, any conventionally known compounds can be used, but they have a heterocyclic group because they are excellent in light resistance, heat resistance, repetitive durability and the like. Fulgides are particularly preferred, and the heterocyclic group is preferably substituted with a group such as a methyl group that is less likely to migrate in terms of repeated durability. Some examples of preferred fulgides are shown below.

[0013]

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[0014]

[Chemical 4]

[0015]

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[0016]

[Chemical 6]

[0017]

[Chemical 7]

[0018]

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[0019]

[Chemical 9] (In the formula, Ph represents a phenyl group.)

[0020]

[Chemical 10]

As the aromatic diamine, any aromatic diamine can be used as long as it can form an imidazole ring or a dihydropyrimidine ring structure by reacting with a portion of the succinic anhydride structure of fulgides. -Diaminobenzene, 4-methyl-1,2-diaminobenzene, 4-ethyl-1,2-diaminobenzene, 4-isopropyl-
1,2-diaminobenzene, 4-tert-butyl-1,2
-Diaminobenzene, 3-methyl-1,2-diaminobenzene, 4,5-dimethyl-1,2-diaminobenzene, 2,3-diaminotetralin, 4-chloro-1,2
-Diaminobenzene, 4-bromo-1,2-diaminobenzene, 3-chloro-1,2-diaminobenzene, 3,
5-dibromo-1,2-diaminobenzene, 4-methoxy-1,2-diaminobenzene, 4-octyloxy-
1,2-diaminobenzene, 4-nitro-1,2-diaminobenzene, 4-cyano-1,2-diaminobenzene, 4-carbomethoxy-1,2-diaminobenzene,
4-sulfamoyl-1,2-diaminobenzene, 3,
4-diaminobenzophenone, 2,3-diaminopyridine, 3,4-diaminopyridine, 2,3-diamino-
5,6-dicyano-pyrazine, 1,2-diaminonaphthalene, 2,3-diaminonaphthalene, 1,8-diaminonaphthalene, 6-methyl-2,3-diaminonaphthalene, 6-chloro-2,3-diaminonaphthalene , 1, 2
-Diaminoanthraquinone and the like.

The fulgides have E-form and Z-form, and from the E-form, the general formula (II)

[0023]

[Chemical 11]

(In the formula, R ₁ , R ₂ and R ₃ each independently represent an alkyl group, an aralkyl group or an aryl group, or R ₂ and R ₃ are linked to represent a cycloalkylidene group,
Het represents an aromatic heterocyclic residue which may have a substituent, and [A] represents a divalent aromatic group which may have a substituent. A compound represented by the formula (hereinafter, referred to as E-iminolactam) is produced, and the compound represented by the general formula (III) is obtained from the Z-form.

[0025]

[Chemical 12]

(In the formula, R ₁ , R ₂ and R ₃ each independently represent an alkyl group, an aralkyl group or an aryl group, or R ₂ and R ₃ are linked to represent a cycloalkylidene group,
Het represents an aromatic heterocyclic residue which may have a substituent, and [A] represents a divalent aromatic group which may have a substituent. )) (Hereinafter, referred to as Z-iminolactam) is produced. If a mixture of E- and Z-forms is used, a corresponding mixture of two iminolactams is obtained. That is, when E-fulgide is reacted, among the two carbonyl groups of the succinic anhydride structure, the carbonyl group on the side of the alkylidene group to which the heterocyclic group is bonded is iminated, but Z-fulgide is When reacted, the carbonyl group on the opposite side is iminated. This is probably due to the steric interaction between the heterocyclic group and the aromatic primary amine.

Z-iminolactam does not exhibit photochromism originally, but the irradiation of ultraviolet rays causes isomerization of the alkylidene group to which the heterocyclic group is bonded, resulting in the general formula (IV).

[0028]

[Chemical 13]

(In the formula, R ₁ , R ₂ and R ₃ each independently represent an alkyl group, an aralkyl group or an aryl group, or R ₂ and R ₃ are linked to represent a cycloalkylidene group,
Het represents an aromatic heterocyclic residue which may have a substituent, and [A] represents a divalent aromatic group which may have a substituent. ), The photochromism is developed.

E-iminolactam and Z-iminolactam may be isolated and used as a single substance, or may be used as a mixture.

As a form of use, it can be dissolved in an appropriate organic solvent and used as a solution. Further, it may be kneaded with a polymer material, or may be dissolved and dispersed in a solution containing the polymer material, coated on an object, and then the solvent may be evaporated. Specific examples of the latter usage form include printing, coating and printing. Those having a long-chain alkyl group can be used as the LB film.

The iminobutyrolactam-based photochromic compound of the present invention is chemically stable, has excellent weather resistance, light resistance, chemical resistance, etc., has a long absorption wavelength, and has a long wavelength in the entire visible region. It has absorption characteristics and exhibits a color close to black depending on the medium, which has characteristics not found in conventional fulgide compounds, and can be suitably used for optical recording materials, display materials, etc. .

[0033]

EXAMPLES The present invention will be described in more detail below with reference to examples. In the following examples, "part" means "part by weight".

Example 1 2-Isopropylidene-3-
[1- (2,5-Dimethylfuran-3-yl) ethylidene] succinic anhydride (furylfulgide: E / Z = 45 /
55) Add 65 parts and 81 parts of 1,2-diaminobenzene to the reactor, heat with stirring to melt, and then 100 ° C.
And reacted for 1 hour. After the reaction was completed, 650 parts of acetic anhydride was added to the reaction mixture, and the mixture was further reacted at 90 ° C. for 3 hours. After acetic anhydride was distilled off under reduced pressure, the residue was dissolved in toluene.
The toluene solution was washed with water and dried, and then toluene was distilled off under reduced pressure to obtain a crude product. The crude product is separated and purified using a column chromatograph (stationary phase: silica gel, mobile phase: n-hexane / ethyl acetate) to obtain the compound of formula (1).

[0035]

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16 parts of the E-iminolactam type compound represented by the formula and the formula (2)

[0037]

[Chemical 15]

13 parts of a Z-iminolactam type compound represented by

Field desorption mass spectrum of compound of formula (1) (hereinafter referred to as FD / MS) m / z 332 (M ⁺ ).

FD / MS m / z 332 (M ⁺ ) of the compound of formula (2)

The compound of formula (1) thus obtained was dissolved in methanol and filtered with a filter (UV-D36C:
When a light from a mercury-xenon lamp (UV spot light source L2859 type: manufactured by Hamamatsu Photonics KK) was irradiated through Toshiba, a solution that was almost colorless developed a clear reddish purple color (λmax 561 nm). This absorption maximum had a longer wavelength of 60 nm than the absorption maximum of furylfulgide (501 nm). Then, the filter was changed to Y-48 (available from
It was replaced by Toshiba) and irradiated with light from the same light source, and it quickly returned to an almost colorless state.

When the compound of the formula (1) was supported on silica gel and irradiated with the above-mentioned ultraviolet light, it developed a dark blue color close to black.

When the compound of the formula (2) was used in place of the compound of the formula (1), a bright red-green color was developed (λmax
576 nm). The initial color density was about one-half that when the compound of formula (1) was used, but it showed similar photochromism, and the color density increased little by little when the cycle of color development-erasing was repeated, and After repeated times, it was equivalent to using the compound of formula (1).

The IR absorption spectrum of the compound of the formula (1) (KBr tablets, the same applies hereinafter) is shown in FIG. 1, the UV-visible absorption spectra of the ring-opened product and the ring-closed product (solvent: methanol, the same below) are shown in FIG. The IR absorption spectrum of the compound of the formula (2) is shown in FIG. 2, the UV-visible absorption spectrum of the ring-opened product and the ring-closed product is shown in FIG. 12, the H-NMR (solvent: deuterated acetone) is shown in FIG. The molecular structures obtained by X-ray diffraction are shown in FIG. 22, respectively.

(Embodiment 2) In Embodiment 1, 1,2-
Formula (3) was obtained in the same manner as in Example 1 except that 112 parts of 1,8-diaminonaphthalene was used instead of 81 parts of diaminobenzene.

[0046]

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19 parts of an E-iminolactam type compound represented by the formula and the formula (4)

[0048]

[Chemical 17]

15 parts of a Z-iminolactam type compound represented by

FD / MS m / z 382 (M ⁺ , 100) 191 (4) of the compound of formula (3)

FD / MS m / z 382 (M ⁺ , 100) 191 (3) of the compound of formula (4)

A compound of formula (3) is dissolved in methanol,
When it was irradiated with ultraviolet light in the same manner as in Example 1, a clear red-green color was formed (λmax 563 nm). The compound of formula (4) had a λmax of 573 nm.

The IR absorption spectrum of the compound of formula (3) is shown in FIG. 3, the UV-visible absorption spectrum of the ring-opened product and the ring-closed product is shown in FIG. 13, and the IR absorption spectrum of the compound of formula (4) is shown in FIG. The UV-visible absorption spectra of the ring-opened product and the ring-closed product are shown in FIG. 14, respectively.

(Example 3) In Example 1, 1,2-
Instead of 81 parts of diaminobenzene, 4-chloro-1,2
Example 1 except that 107 parts of diaminobenzene were used
In the same manner as in equation (5)

[0055]

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(Wherein one of R and R'represents Cl and the other represents H), and 11 parts of an E-iminolactam type compound represented by the formula (6)

[0057]

[Chemical 19]

7 parts of a Z-iminolactam type compound represented by the formula (wherein one of R and R'represents Cl and the other represents H) was obtained.

FD / MS m / z 366 (M ⁺ , 100) 368 (18) 1 of the compound of formula (5)
83 (3)

FD / MS m / z 366 (M ⁺ , 100) 368 (31) 1 of the compound of formula (6)
83 (2)

The compound of formula (5) is dissolved in methanol,
When it was irradiated with ultraviolet light in the same manner as in Example 1, a bright red-green color was developed (λmax 564 nm). The compound of formula (6) had a λmax of 583 nm.

The IR absorption spectrum of the compound of formula (5) is shown in FIG. 5, the UV-visible absorption spectrum of the ring-opened product and the ring-closed product is shown in FIG. 15, and the IR absorption spectrum of the compound of formula (6) is shown in FIG. The UV-visible absorption spectra of the ring-opened product and the ring-opened product are shown in FIG. 16, respectively.

(Embodiment 4) In Embodiment 1, 1,2-
4-Methyl-1,2 instead of 81 parts of diaminobenzene
-In the same manner as in Example 1 except that 92 parts of diaminobenzene was used, the formula (7)

[0064]

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(Wherein one of R and R'represents CH ₃ and the other represents H) 11 parts of the E-iminolactam type compound represented by the formula and formula (8)

[0066]

[Chemical 21]

7 parts of a Z-iminolactam type compound represented by the formula (wherein one of R and R'represents CH ₃ and the other represents H) was obtained.

FD / MS m / z 346 (M ⁺ , 100) 173 (9) of the compound of formula (7)

FD / MS m / z 346 (M ⁺ , 100) 173 (3) of the compound of formula (8)

The compound of formula (7) is dissolved in methanol,
When it was irradiated with ultraviolet light in the same manner as in Example 1, a clear red-green color was formed (λmax 560 nm). The compound of formula (8) had a λmax of 558 nm.

The IR absorption spectrum of the compound of formula (7) is shown in FIG. 7, the UV-visible absorption spectrum of the ring-opened product and the ring-closed product is shown in FIG. 17, and the IR absorption spectrum of the compound of formula (8) is shown in FIG. The UV-visible absorption spectra of the ring-opened product and the ring-closed product are shown in FIG. 18, respectively.

Example 5 In Example 1, instead of 65 parts of furylflugide, 2-isopropylidene-3-
[1- (2,5-Dimethylthiophen-3-yl) ethylidene] succinic anhydride (thienyl fulgide: E / Z =
4/96) in the same manner as in Example 1 except that 69 parts were used and the formula (9)

[0073]

[Chemical formula 22]

14 parts of an E-iminolactam type compound represented by the formula and the formula (10)

[0075]

[Chemical formula 23]

7 parts of a Z-iminolactam type compound represented by

FD / MS m / z 348 (M ⁺ , 100) 174 (4) of the compound of formula (9)

FD / MS m / z 348 (M ⁺ , 100) 173 (2) of the compound of formula (10)

The compound of formula (9) is dissolved in methanol,
When it was irradiated with ultraviolet light in the same manner as in Example 1, a bright red-green color was developed (λmax 567 nm). The compound having the formula (10) had a λmax of 565 nm.

The IR absorption spectrum of the compound of formula (9) is shown in FIG. 9, the UV-visible absorption spectrum of the ring-opened product and the ring-closed product is shown in FIG. 19, and the IR absorption spectrum of the compound of formula (10) is shown in FIG. The UV-visible absorption spectra of the ring-opened product and the ring-closed product are shown in FIG. 20, respectively.

Example 6 2 parts of the compound of the formula (2) obtained in Example 1, 20 parts of Aerosil and a phenol resin varnish for lithographic ink [MG-63: manufactured by Dainippon Ink and Chemicals, Inc.]
80 parts were kneaded to prepare an ink. Using the ink thus obtained, a test printing machine (2800CD type: manufactured by Ryobi Co., Ltd.) was used to print on white paper to prepare test pieces.

The obtained test piece was put on a filter [UV-D
36C: made by Toshiba Corporation] mercury-xenon lamp [UV spot light source L2859 type: Hamamatsu Photonics
(Manufactured by K.K. Co., Ltd.), the printed portion, which was almost colorless, developed a bright reddish purple color. Then, the filter was replaced with L-42 (manufactured by Toshiba Corporation) and irradiated with light from the same light source, and the color quickly returned to an almost colorless state. When this operation was repeated, it could be repeated 1000 times or more.

Example 7 In Example 6, the formula (2)
Except that the compound of formula (3) was used in place of the compound of
When a test piece was prepared in the same manner as in Example 6 and the same test as in Example 6 was carried out, it was possible to repeat the coloring-decoloring cycle 1000 times or more.

(Embodiment 8) In Embodiment 6, the formula (2) is used.
Except that the compound of formula (5) was used in place of the compound of
When a test piece was prepared in the same manner as in Example 6 and the same test as in Example 6 was carried out, it was possible to repeat the coloring-decoloring cycle 1000 times or more.

Example 9 In Example 6, the formula (2)
Except that the compound of formula (9) was used in place of the compound of
When a test piece was prepared in the same manner as in Example 6 and the same test as in Example 6 was carried out, it was possible to repeat the coloring-decoloring cycle 1000 times or more.

Example 10 In Example 6, instead of the compound of formula (2), an iminolactam type compound (E-form, Z-form) obtained from furylfulgide and 4-methoxy-1,2-diaminobenzene Mixture of FD-MS m
/ Z 362) was used, and a test piece was prepared in the same manner as in Example 6.

When the same test as in Example 6 was carried out, 1
It was possible to repeat the color development-decolorization cycle 000 times or more.

Example 11 In Example 6, instead of the compound of the formula (2), 2-adamantylidene-3-
[1- (2,5-dimethylfuran-3-yl) ethylidene] succinic anhydride and an iminolactam-type compound (mixture of E-form and Z-form, FD-MS m obtained from 1,2-diaminobenzene / Z 434) was used, and a test piece was prepared in the same manner as in Example 6.

When the same test as in Example 6 was conducted, 1
It was possible to repeat the color development-decolorization cycle 000 times or more.

COMPARATIVE EXAMPLE 1 In Example 6, the formula (2)
A test piece was prepared in the same manner as in Example 6 except that furyl fulgide was used in place of the compound in Example 6, and the same test as in Example 6 was performed. After repeating 450 cycles of color development-decolorization. Stopped showing photochromism.

Further, when a separately prepared test piece was stored in the dark for 6 months and then tested in the same manner as in Example 6, no remarkable photochromism was shown.

(Comparative Example 2) In Example 6, the formula (2)
A test piece was prepared in the same manner as in Example 6 except that thienyl fulgide was used in place of the compound of Example 1, and the same test as in Example 6 was carried out. After repeating, it stopped showing photochromism.

(Example 12) 2- (1-octadecylethylidene) -3- [1- (2,5-dimethylfuran-3)
-Yl) ethylidene] succinic anhydride and an iminolactam-type compound (mixture of E-form and Z-form, FD-MS m / z 620) 1 obtained from 2,3-diaminonaphthalene
4 parts of acrylic resin [Acridic A-181: Dainippon Ink and Chemicals, Inc.] was dissolved in 100 parts of methyl ethyl ketone, and then spin coated on a glass plate to prepare a test piece.

When the same test as in Example 6 was conducted, 1
It was possible to repeat the color development-decolorization cycle 000 times or more.

Example 13 Obtained from 2- (1-phenylethylidene) -3- [1- (2,5-dimethylfuran-3-yl) ethylidene] succinic anhydride and 3,4-diaminobenzophenone. Iminolactam-type compound (mixture of E-form and Z-form, FD-MS m / z 498) 1
0 parts, nitrocellulose [NC H20: Asahi Kasei
Co., Ltd.] and polyamide resin [REOamide S-650]
[0: manufactured by Kao Corporation] 40 parts of a varnish for gravure ink, 50 parts of methyl ethyl ketone, and 50 parts of toluene were kneaded to prepare a gravure ink. The gravure ink thus obtained was used to print on a blank sheet of paper with a test printing machine [TM type: manufactured by Toya Iron Works Co., Ltd.] to prepare test pieces.

When the same test as in Example 6 was conducted, it was found to be 1
It was possible to repeat the color development-decolorization cycle 000 times or more.

[0097]

INDUSTRIAL APPLICABILITY The iminobutyrolactam photochromic material according to the present invention is excellent in image stability, heat resistance and repetitive durability, and exhibits a very clear color development state. It can be advantageously used for materials, decorations, etc.

[Brief description of drawings]

1 is an IR absorption spectrum of the compound of formula (1) obtained in Example 1. FIG.

2 is an IR absorption spectrum of the compound of formula (2) obtained in Example 1. FIG.

3 is an IR absorption spectrum of the compound of formula (3) obtained in Example 2. FIG.

4 is an IR absorption spectrum of the compound of formula (4) obtained in Example 2. FIG.

5 is an IR absorption spectrum of the compound of formula (5) obtained in Example 3. FIG.

6 is an IR absorption spectrum of the compound of formula (6) obtained in Example 3. FIG.

7 is an IR absorption spectrum of the compound of formula (7) obtained in Example 4. FIG.

8 is an IR absorption spectrum of the compound of formula (8) obtained in Example 4. FIG.

9 is an IR absorption spectrum of the compound of formula (9) obtained in Example 5. FIG.

10 is an IR absorption spectrum of the compound of formula (10) obtained in Example 5. FIG.

11 is an ultraviolet-visible absorption spectrum of the compound of formula (1) obtained in Example 1. FIG.

12 is an ultraviolet-visible absorption spectrum of the compound of formula (2) obtained in Example 1. FIG.

13 is an ultraviolet-visible absorption spectrum of the compound of formula (3) obtained in Example 2. FIG.

14 is an ultraviolet-visible absorption spectrum of the compound of formula (4) obtained in Example 2. FIG.

15 is an ultraviolet-visible absorption spectrum of the compound of formula (5) obtained in Example 3. FIG.

16 is an ultraviolet-visible absorption spectrum of the compound of formula (6) obtained in Example 3. FIG.

17 is an ultraviolet-visible absorption spectrum of the compound of formula (7) obtained in Example 4. FIG.

18 is an ultraviolet-visible absorption spectrum of the compound of formula (8) obtained in Example 4. FIG.

19 is an ultraviolet-visible absorption spectrum of the compound of formula (9) obtained in Example 5. FIG.

20 is an ultraviolet-visible absorption spectrum of the compound of formula (10) obtained in Example 5. FIG.

FIG. 21: H-NM of the compound of formula (2) obtained in Example 1.
It is an R spectrum.

22 is a molecular structure of a single crystal of the compound of formula (2) obtained in Example 1 by X-ray diffraction. FIG.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI technical display location G11B 7/24 516 7215-5D

Claims (9)

[Claims] 1. A compound of the general formula (I) (In the formula, [A] represents a divalent aromatic group which may have a substituent, and at least one of R ₂ , R ₃ and R ₄
One group represents an aromatic heterocyclic residue which may have a substituent, and the remaining two groups and R ₁ are each independently an alkyl group, an aralkyl group or an aryl group, or R ₁ and R ₂ Of the combinations and combinations of R ₃ and R ₄ ,
The two groups in the combination having no aromatic heterocyclic residue which may have a substituent are linked to each other to represent a cycloalkylidene group. ) An iminobutyrolactam compound represented by 2. The iminobutyrolactam compound according to claim 1, wherein R ₂ is an aromatic heterocyclic residue which may have a substituent. 3. The iminobutyrolactam compound according to claim 1, wherein R ₃ is an aromatic heterocyclic residue which may have a substituent. 4. The iminobutyrolactam compound according to claim 1, wherein R ₄ is an aromatic heterocyclic residue which may have a substituent. 5. An aromatic heterocyclic residue is a furyl group, a thienyl group or a pyryl group, and [A] is a 1,2-phenylene group or 1,1 substituted with an alkyl group, an alkoxy group or a halogen atom. The iminobutyrolactam compound according to claim 1, 2, 3, or 4 which is a 2-, 2,3- or 1,8-naphthylene group. 6. The method for producing an iminobutyrolactam compound according to claim 1, wherein a fulgide compound and an aromatic diamine are reacted. 7. An aromatic diamine having an alkyl group, an alkoxy group or a halogen atom as a substituent, 1,2-
The method according to claim 6, which is a phenylenediamine derivative or 1,2-, 2,3- or 1,8-naphthylenediamine. 8. The fulgide compound is a compound having a furyl group, a thienyl group or a pyryl group.
The manufacturing method described. 9. A photochromic material containing the iminobutyrolactam compound according to claim 1, 2, 3, 4, or 5.