JP2004307486A - Method for producing intermolecular compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an intermolecular compound for providing light control materials excellent in optical/electric characteristics in producing the intermolecular compound of an alkali earth metal periodide with a heterocyclic compound. <P>SOLUTION: The method for producing the intermolecular compound of the alkali earth metal periodide is to bond iodine (i) and the alkali earth metal iodide (ii) with the heterocyclic compound (iii) in a solvent by irradiating ultrasonic waves or irradiating the ultrasonic waves after the bonding. The ultrasonic waves having 20-30 kHz frequency and 100-2000 W output power are irradiated. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a method for producing an intermolecular compound.

The organic intermolecular compound belonging to one kind of the intermolecular compound is a general term for compounds in which an organic compound is added to an inorganic compound or an organic compound at a fixed or multiple molecular ratio. As the former example, CaCl ₂ .4CH ₃ OH and PtCl ₄ .2 (CH ₃ NH ₂ .HCl) are known. The bond between each component molecule in such an organic intermolecular compound is based on the residual affinity in the unsaturated state of atoms such as oxygen and nitrogen or carbon (for example, see Non-Patent Document 1).

As the organic intermolecular compound, an intermolecular compound of an alkaline earth metal periodate and a heterocyclic compound is known in addition to those described above. For example, as a polarizing particle contained in a light control material such as SPD (Suspended Particle Device), as an intermolecular compound (needle-like small crystal particle) as described above, a periodate comprising calcium iodide and iodine and a pyrazine are used. There is an intermolecular compound composed of dicarboxylic acid and water (for example, see Patent Document 1). The _{structure, xC 6 H 4 N 2 O} 4 · CaI 2 · yI 2 · zH 2 O (x: 1~4, y: 1~6, z: 2~10) is estimated to be such.

  Such an intermolecular compound is obtained by bonding iodine (i), alkaline earth metal iodide (ii) and heterocyclic compound (iii) while irradiating ultrasonic waves in a solvent or after bonding. It is known that it can be obtained by irradiating a sound wave (for example, see Patent Documents 2, 3, 4, and 5).

  However, depending on the conditions of ultrasonic irradiation, when the obtained intermolecular compound is used as a polarizing particle, there is a drawback that the optical / electrical properties as a light modulating material cannot be sufficiently exhibited.

  In the case where pigment particles are stably dispersed in a liquid medium as in the preparation of an aqueous ink for ink jet recording, it is also necessary to irradiate ultrasonic waves at a relatively high frequency such as 40 kHz. Is known (for example, see Patent Document 6).

Edited by Toshi Inoue et al., "Iwanami Physical and Chemical Dictionary, Revised Edition", 8th Revised Edition, Iwanami Shoten Co., Ltd., April 5, 1965, p. 1356. U.S. Pat. No. 6,517,746 (column 5, line 60 to column 6, line 18). JP-A-6-129168 (Page 10, paragraph 0043). JP-A-2002-82364 (page 8, paragraph number 0037). JP-A-2002-189123 (page 8, paragraph number 0044). JP-A-2002-214653 (page 8, paragraph number 0038). JP-A-10-60331 (page 8, paragraph number 0058).

  An object of the present invention is to provide an intermolecular compound of an alkaline earth metal periodate and a heterocyclic compound, which is excellent as a light modulating material in optical and electrical properties.

  Therefore, the present inventors have conducted intensive studies in view of the above situation, and as a result, obtained an intermolecular compound by changing the frequency of the ultrasonic wave applied during the production of the intermolecular compound, and evaluated the performance as a light modulating material. As a result, the optical / electrical properties greatly depend on the frequency of irradiation, and surprisingly, the chemical substances that form the particles are different. As a result, the optical / electrical properties are similar at the same frequency as when preparing the aqueous ink for inkjet recording. Particles were not obtained, but rather, only when subjected to ultrasonic irradiation at a lower frequency, it was found that polarizing particles with excellent optical and electrical properties were obtained as a light control material, and the present invention was completed. .

  That is, the present invention relates to a method of bonding iodine (i), an alkaline earth metal iodide (ii) and a heterocyclic compound (iii) in a solvent while irradiating them with ultrasonic waves, or irradiating ultrasonic waves after bonding. Method for producing an intermolecular compound consisting of an alkaline earth metal periodate and a heterocyclic compound, characterized in that ultrasonic irradiation is performed at a frequency of 20 to 30 kHz and an output of 100 to 2000 W, comprising: And a method for producing an intermolecular compound of a compound and a heterocyclic compound.

  According to the production method of the present invention, an intermolecular compound that becomes a polarizing particle having excellent optical and electrical properties can be produced as a light control material.

  Hereinafter, the present invention will be described in detail.

  The intermolecular compound to be produced in the present invention is an intermolecular compound of an alkaline earth metal periodate and a heterocyclic compound (a precursor of particles) (hereinafter abbreviated as an intermolecular compound).

  This alkaline earth metal periodate is iodine (i) [hereinafter abbreviated as component (i). ] And alkaline earth metal iodide (ii) [hereinafter abbreviated as component (ii). And the intermolecular compound of the final product is a mixture of the alkaline earth metal periodate and the heterocyclic compound (iii) [hereinafter abbreviated as component (iii). ] Can be obtained.

  Component (i) is iodine, and preferably has low crystallinity in order to be rapidly dissolved in a solvent. Examples of the alkaline earth metal iodide of the component (ii) include calcium iodide, magnesium iodide, strontium iodide, and barium iodide. Among them, an intermolecular compound is formed with the component (iii) described below. Calcium iodide is preferred because of its ease. Since calcium iodide deliquesces in the atmosphere, it is preferable to select and use one having the lowest possible moisture content, which is removed by heating and drying under reduced pressure to remove water of crystallization and stored in a closed container containing a desiccant. .

  The alkaline earth metal periodate can be obtained by combining the components (ii) at a charge ratio of 1 to 6 moles per mole of the component (ii) in terms of moles. The end point of the coupling can be determined by the consumption of component (i). Generally, this bonding takes 3 minutes to 5 hours at a temperature of 5 to 90 ° C.

  The intermolecular compound in the present invention can be obtained by binding component (i), component (ii), and component (iii) in a solvent, as in the background art. However, when producing the intermolecular compound having excellent optical and electrical properties as a light modulating material, the component (i) and the component (ii) are uniformly dissolved in a solvent, and then the mixture is mixed with the complex. It is preferable to bond with the cyclic compound (iii) by mixing. As a specific means, the components (i) and (ii) can be sufficiently dissolved in a solvent in a short time without requiring any special device, and requiring less time. A more preferred method is to heat at least one of (ii) and the solvent, then mix the remaining components and heat to dissolve. Among them, a method in which the solvent and the component (ii) are dissolved by heating and then the component (i) is mixed and then dissolved by heating is particularly preferable. Dissolving the components (ii) and (i) at a temperature of 30 to 80 ° C., especially 40 to 60 ° C., can promptly shift to bonding to the component (iii) in the next step. It is particularly preferable in this respect.

  In forming the bond, stirring is preferably performed so that the temperature of the mixture becomes uniform and constant. The time required for the formation of this iodide can be selected from a range of 5 minutes to 3 hours at a temperature of 30 to 80 ° C, and preferably 15 minutes to 2 hours at a temperature of 40 to 60 ° C. .

  The solvent used for preparing the mixture is more easily dissolving the component (i), the component (ii), and the polymer dispersion stabilizer described below, and the component (iii) described below and an intermolecular compound as a final product. It is preferable to select and use those which are more difficult to dissolve. It is more preferable to use an organic solvent as an essential solvent at this time. The amount of the solvent is preferably 7 to 20 times the total amount of the component (i), the component (ii), and the component (iii) described below in terms of mass.

  Examples of the organic solvent include any known and common organic solvents, for example, ethyl acetate, butyl acetate, pentyl acetate, acetic acid organic solvents such as hexyl acetate, methanol, ethanol, monoalcohol organic solvents such as isopropanol. And the like.

  In the case of obtaining the intermolecular compound used as a polarizing particle of a light modulating material described later, it is preferable to use water in combination in order to promote the binding smoothly and control the particle diameter. The amount of water is preferably equivalent to 1 to 20% of the total amount of component (i), component (ii), and component (iii) described below in terms of mass.

  When water is used in combination, it is preferable to use the monoalcohol-based organic solvent as an essential component in order to increase the affinity between water and the organic solvent. When the polymer dispersion stabilizer described below does not dissolve in the monoalcohol-based organic solvent, it is preferable to use another organic solvent in combination.However, the amount of the monoalcohol-based organic solvent added at this time is, in terms of mass, It is preferable that the amount is equivalent to 1 to 150% of the total amount of the component (i), the component (ii), and the component (iii) described later.

  In order to stably disperse a component (iii) described later and an intermolecular compound formed by a bond between the periodate and the component (iii) in a mixture without dissolving or settling, a polymer type dispersion stabilizer is used. It is preferable to use them in combination. Examples of such a polymeric dispersion stabilizer include those which are soluble in a solvent, for example, nitrocellulose, polyvinyl alcohol, gelatin, casein, or a portion having a high affinity for an intermolecular compound (A) and an affinity for a solvent. AB block copolymer composed of a portion (B) having a high molecular weight. These polymeric dispersion stabilizers may be used alone or in combination. The amount of the polymer type dispersant is preferably equivalent to 1 to 200% of the total amount of the component (i), the component (ii) and the component (iii) described later, and more preferably 20 to 150%. % Is more preferable.

  The desired intermolecular compound can be obtained by mixing and combining the thus obtained primary product of periodate and the component (iii). As such a component (iii), a compound containing a nitrogen atom in a heterocyclic ring (nitrogen-containing heterocyclic compound) is preferable because an intermolecular compound is easily formed with the alkaline earth metal periodate. .

  Specifically, anhydrous glycine (2,5-piperazinedione), 5,6-dihydrouracil, urazole, succinimide, glycoluril (acetylene urea), hydantoin, anhydrous alanine (3,6-dimethyl-2,5-piperazine) Dione), 3-methoxy-2- (1H) pyridone, quinaldic acid, 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid, pyrazine-2,3-dicarboxylic acid, pyrazine-2,5-dicarboxylic acid, Pyrazine acid (2-carboxypyrazine), 4-hydroxyquinaldic acid, 4-methoxyquinaldic acid, pyridine-2-carboxylic acid, pyridine-2,5-dicarboxylic acid, picolinic acid, 2-hydroxypyridine, barbituric acid, 8-hydroxyquinoline, cycloleucine, and 2,2′-dipyridyl and the like. Of these, pyrazine-2,3-dicarboxylic acid dihydrate, pyrazine-2,5-dicarboxylic acid dihydrate and pyrazine-2,5-dicarboxylic acid monohydrate are preferred.

  Component (iii) is preferably charged so as to be 1 to 4 moles, more preferably 2 moles, per mole of alkaline earth metal periodate as a primary product.

  The bond between the alkaline earth metal periodate as the primary product and the component (iii) can be selected from the range of 30 to 80 ° C. for 5 minutes to 10 hours. Stirring can further promote this binding. When a solvent in which the component (iii) was not dissolved was selected and used as the solvent at this time, the point at which the absence of the component (iii) could be confirmed by microscopic observation of the mixture over time was confirmed by the fact that this bond was not used. It is possible to determine the end point. Generally, this bonding takes 30 minutes to 5 hours at a temperature of 40-60 ° C.

  In the present invention, bonding is performed while irradiating ultrasonic waves, or ultrasonic wave irradiation is performed after bonding to produce an intermolecular compound composed of an alkaline earth metal periodate and a heterocyclic compound. In the case of bonding while irradiating with ultrasonic waves, the irradiation target is a mixture containing an intermolecular compound consisting of iodine (i), alkaline earth metal iodide (ii), and heterocyclic compound (iii) and a solvent. On the other hand, the object to be irradiated with ultrasonic waves after bonding is a mixture containing a solvent and an intermolecular compound composed of an alkaline earth metal periodate (ii) and a heterocyclic compound (iii).

  The ultrasonic wave is defined as a sound wave having a frequency of 20 kHz or more in Japanese Industrial Standard JIS Z 2300. The frequency of the ultrasonic wave employed in the present invention is 20 to 30 kHz. That is, in the present invention, the lowest frequency is selectively adopted from a wide range of ultrasonic frequencies.

  The irradiation output of the ultrasonic wave is selected according to the amount of the mixture to be irradiated, but it is preferable that the output be 100 to 2000 W. Within the above range, as the output is larger, the irradiation time can be shortened, and the productivity can be further improved.

  The temperature of the mixture at the time of ultrasonic irradiation is preferably set to 20 to 60 ° C. As the temperature is higher, the irradiation time can be shortened and the productivity can be further improved, but the intermolecular compound of the present invention has a property of being thermally decomposed even in a small amount in the mixture to be bonded. In the temperature range higher than the range, the optical and electrical properties of the obtained intermolecular compound become insufficient. Since the temperature rise of the liquid medium due to the ultrasonic irradiation is more intense than expected, it is preferable to cool the outside of the container containing the mixture with cooling water or the like in order to maintain the above-mentioned temperature range.

  The ultrasonic irradiation time can be set to 5 minutes to 5 hours depending on the irradiation output. In this case, in the case of using a polymer type dispersant as described above in combination, excessive ultrasonic irradiation causes desorption of the polymer type dispersion stabilizer adsorbed on the intermolecular compound and causes aggregation of particles. Sometimes. Therefore, it is preferable to stop the ultrasonic irradiation when the light modulating material is prepared using the intermolecular compound to be irradiated and the optical / electrical characteristics are maximized. The optical and electrical characteristics can be easily confirmed by, for example, sampling each time under the same conditions and preparing and measuring a dimming panel or the like described later using them.

  The bonding may be carried out while irradiating ultrasonic waves. However, since the bonding is preferably performed at 40 to 60 ° C. for 30 minutes to 5 hours as described above, the polymer dispersion stabilizer may be thermally decomposed or excessively irradiated. In order to suppress desorption or reduce the energy required for irradiation, it is more preferable to perform ultrasonic irradiation after the above-mentioned coupling so that ultrasonic irradiation can be performed in a shorter time.

  Due to the ultrasonic vibration at the specific frequency and the specific output, the aggregated or agglomerated polarized particles can be disintegrated more finely as compared to a case where this condition is not satisfied. Can exhibit excellent optical and electrical characteristics.

  By optimizing the type of solvent and the amount used, the type of polymer dispersion stabilizer and the amount used, and the like, the present invention can prevent only the intermolecular compound from being dissolved in the mixture.

  The mixture obtained under the optimized conditions is a dispersion of an intermolecular compound having a high purity and a very narrow particle size distribution. By removing substances and coarse particles, the purity can be further improved and the particle size distribution can be further narrowed. Unbound solids and coarse particles can be removed by centrifugation of the dispersion. Unbound lysates and fines can be removed as supernatant by centrifuging only the required particles from the dispersion. The particles that have been centrifugally settled can be returned to a dispersion by dispersing the particles in a solvent that dissolves the polymer type dispersion stabilizer without dissolving the particles.

  Specifically, by performing the following treatment, it is possible to selectively obtain only an intermolecular compound having an extremely high purity and an extremely narrow particle size distribution. First, the reaction mixture of the intermolecular compound bound under the optimized conditions is irradiated with ultrasonic waves to completely disperse it to the primary particle level. Next, centrifugation is performed with a strong centrifugal force of 7500 G or more to settle most of the particles. After discarding the supernatant, a solvent in which a polymer type dispersion stabilizer is dissolved is added to the precipitate, and the precipitate is re-dispersed by ultrasonic irradiation. Next, centrifugal separation is performed with a weak centrifugal force of 2000 G or less to settle solids and coarse particles that have not formed an intermolecular compound. The supernatant is transferred to another container and centrifuged at a strong centrifugal force of 5000 G or more to settle appropriate particles. After discarding the supernatant, a solvent is added to the precipitate, and the precipitate is irradiated with ultrasonic waves to be redispersed. The dispersion of the intermolecular compound thus obtained exhibits very excellent optical and electrical properties when used as a light modulating material. By drying and removing the solvent from the dispersion of the intermolecular compound, a dry intermolecular compound can be obtained.

  In the process of the redispersion, by irradiating the ultrasonic waves under the conditions described above, it is possible to disperse in a shorter time, the thermal decomposition of an undesirable intermolecular compound or the high molecular weight dispersion stabilizer due to excessive irradiation. Desorption can be suppressed, and productivity can be significantly improved.

  In the manufacturing method of the present invention, the ultrasonic irradiation can be performed in any of the above-described manufacturing steps. For example, the ultrasonic irradiation can be performed in each of the ultrasonic dispersion steps in the flowchart shown in FIG.

  By carrying out the production method of the present invention under the conditions combining the preferable conditions as described above, the particle size (average particle size) is 1000 nm or less in a long diameter, preferably 100 to 1000 nm, more preferably 200 to 500 nm, In addition, a rod-shaped intermolecular compound having a particle aspect ratio of 1.1 to 10.0, preferably 2.0 to 7.0 can be obtained in high yield. The size of the particles and the aspect ratio thereof can be calculated from the values measured by a transmission electron microscope. Specifically, the former is calculated as the average of the major axis of 50 randomly selected particles of the same particle, and the latter is calculated as the average of the ratio of the major axis to minor axis of 50 randomly selected particles of the same particle. Can be.

  The intermolecular compound thus obtained can be used for various applications as in the past, but can be used, for example, as polarizing particles of a light control material.

  The mixture is a dispersion of polarizing particles and can be used as a light modulating material as it is. In order to obtain a light control panel from this light control material, for example, the mixture is diluted with a solvent that dissolves the polymer type dispersion stabilizer without dissolving the polarizing particles, and then injected into the light control characteristic measurement cell. As the cell, for example, a cell in which the ends of two transparent conductive substrates described later, which are arranged in parallel at an interval of 35 mil, are sealed and an electrode connection portion is provided on the substrate can be used. The cell into which the light modulating material has been injected shows a dark blue color due to the color of the polarizing particles, but when an AC voltage is applied, the polarizing particles are arranged in parallel to the electric field, so that the cell becomes transparent.

  The yield of the intermolecular compound having an appropriate particle size as the light modulating material can be replaced with, for example, the optical and electrical characteristics of the polarizing particle dispersion. That is, the contrast (absorbance before voltage application / absorbance after voltage application) and decay time (time required until the absorbance recovers 90% after voltage application) when an AC voltage having a frequency of 10 kHz and 350 V is applied to the cell. Can be used as an index. Intermolecular compounds having a contrast in the range of 1.4 to 2.5 (-) and a decay time in the range of 5 to 9 (milliseconds) are suitable as polarizing particles of the light control material.

  As the light modulating material, the mixture can be used as it is as described above. However, it is difficult to process the mixture in a liquid state. Therefore, a dispersion that can be processed into a film is preferable. As such a dispersion, a suspension in which the above-described polarizing particles are dispersed in a liquid (meth) acrylic resin (hereinafter, abbreviated as a polarizing particle suspension) is emulsified in a liquid silicone resin (hereinafter, referred to as a liquid silicone resin). , Polarizer particle emulsion). The liquid (meth) acrylic resin can partially dissolve the polymer dispersion stabilizer of the polarizing particles, and has a function of allowing the polarizing particles to flow without aggregating. On the other hand, the liquid silicone resin is incompatible with the (meth) acrylic resin and has a refractive index equivalent to that of the (meth) acrylic resin. Further, the liquid silicone resin has curability due to having a polymerizable ethylenically unsaturated double bond in the molecule, and has Has the function of enabling the polarizing particle suspension to be processed into a film shape. Incidentally, a photoinitiator and / or an ultraviolet absorber or an antioxidant for accelerating the photocuring of the silicone resin can be added to the polarizing particle emulsion.

  The suspension of the polarizing particles is preferably composed of, in terms of mass, 1 to 70% of the polarizing particles and 30 to 99% of the (meth) acrylic resin, and 4 to 50% of the polarizing particles and the (meth) acrylic resin. More preferably, it is comprised between 50 and 96%. The polarizing particle suspension may contain 1 to 80% of a plasticizer.

  On the other hand, the polarizing particle emulsion is 1 to 100 parts, preferably 20 to 70 parts, more preferably 40 to 65 parts of the polarizing particle suspension per 100 parts of the silicone resin in terms of mass. Can be prepared.

  Further, it is preferable that the emulsion of the polarizing particle suspension in the polarizing particle emulsion is emulsified such that the average particle diameter of the droplets is 1 to 10 μm. Here, the average particle diameter of the droplets of the polarized particle suspension is determined by using a light microscope (Biological Microscope BX-60 manufactured by Olympus Corporation) with a 20-fold objective lens to convert a visual field image into digital data using a computer. It can be calculated by using capture and image processing integration software (Win Roof manufactured by MITANI CORPORATION). Further, the particle size distribution can also be calculated.

  The polarizing particle emulsion obtained in this manner is applied to a transparent conductive substrate and irradiated with ultraviolet rays, electron beams, or the like, whereby the (meth) acrylic resin containing the polarizing particles in a flowable state is contained. A film-like light control layer in which droplets are dispersed in a cured silicone resin can be closely laminated on a substrate. The substrate with the dimming layer is adhered to the transparent conductive substrate such that the dimming layer is on the inner side, or the substrates with the dimming layer are adhered to each other with the dimming layers being on the inner side. An optical panel can be manufactured. The thickness of the light control layer at this time is not particularly limited, but is preferably set to 10 to 200 μm.

  As the transparent conductive substrate, for example, any substrate provided with an inorganic conductive compound such as indium tin oxide, stannous oxide, indium oxide, or an organic conductive polymer can be used. These compounds are used as electrodes because they are transparent and have excellent conductivity. Of course, a glass plate, a synthetic resin sheet or film, or the like can be used as the transparent substrate.

  The light control panel thus obtained can be used, for example, for indoor and outdoor partitions (partitions), window glass / skylight for buildings, various flat display elements used in the electronics industry and video equipment, various instrument panels, and existing liquid crystal displays. Used as a substitute for element, optical shutter, various indoor / outdoor advertising and information display boards, window glass for aircraft / railway vehicles / ships, window glass for automobiles / rearview mirror / sunroof, glasses, sunglasses, sun visor, etc. You can do it.

  Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples. The present invention is not limited to these examples. Unless otherwise specified, (%) and (parts) are based on mass.

(Synthesis example 1)
In a solution of 9.91% nitrocellulose (Asahi Kasei Kogyo Co., Ltd., LIG1 / 8: LIG1 / 4 = 79: 21) dissolved in 2120 g of isoamyl acetate, 42.4 g of calcium iodide, 32.0 g of methanol and pure water are required. (I.e., the amount obtained by subtracting the water content of nitrocellulose in isoamyl acetate, calcium iodide, and methanol from 14.2 g), immersed in a water bath maintained at 45 ° C, and stirred for 15 minutes to complete the calcium iodide. Was dissolved. Next, 72.0 g of iodine was added, and the mixture was stirred at the same temperature for 30 minutes to completely dissolve iodine, thereby obtaining calcium periodate. When 48.0 g of pyrazine-2,5-dicarboxylic acid dihydrate was added to this solution and stirring was continued at the same temperature, the hue of the mixture changed from brown to dark green after 1 to 2 minutes. Further, stirring was continued for 3 hours to obtain a dispersion of the intermolecular compound (corresponding to the step of particle synthesis in FIG. 1).

  Water was filled in a water tank of a 28 kHz, 150 W ultrasonic dispersing machine (SUC2815T-FS type manufactured by Shibuya Electric Works), and a low-temperature constant-temperature water circulation device was connected to keep the water temperature constant at 25 ° C. Here, 100 g of the dispersion obtained in Synthesis Example 1 was collected in a glass sealed container and irradiated with ultrasonic waves for 1 hour (corresponding to the step of ultrasonic dispersion 1 in FIG. 1). Due to this ultrasonic irradiation, the distributions of the average particle diameter and the aspect ratio were all narrower than immediately after the execution of Synthesis Example 1. One hour after the ultrasonic irradiation, a part of the dispersion was diluted with isoamyl acetate and injected into the light control characteristic measuring cell to measure optical and electrical characteristics. The contrast and the decay time were as shown in Table 1.

  As the dimming characteristic measuring cell, a cell in which the ends of two transparent conductive substrates arranged in parallel at an interval of 35 mils were sealed and an electrode connection portion was attached to the substrates was used. The optical and electrical characteristics were evaluated based on the contrast and the decay time when an AC voltage having a frequency of 10 kHz and 350 V was applied to the cell. Polarized particles with higher contrast and shorter decay times are suitable as light modulating materials.

(Comparative Example 1)

  The same operation as in Example 1 was performed except that a 43 to 47 kHz, 230 W ultrasonic dispersing machine (57X type manufactured by NEY DENTAL INTERNATIONAL) was used, and the optical and electrical characteristics were measured by irradiating ultrasonic waves for 1 hour. This also corresponds to the ultrasonic irradiation in the step of ultrasonic dispersion 1 in FIG. The contrast and the decay time were as shown in Table 1.

                          Table 1

  As can be seen from the comparison between Example 1 and Comparative Example 1 in Table 1, at the same ultrasonic irradiation time, the manufacturing method of Example 1 in which the frequency of the irradiated ultrasonic wave is smaller is higher than that of the manufacturing method in Example 1. As compared with the production method of Example 1, an intermolecular compound having excellent optical properties (contrast) as a light modulating material is easily obtained, and as a result, the production method of Example 1 is used for a light modulating panel in which light and darkness is clearer. It is clear that the method is suitable for producing an intermolecular compound. Similarly, the decay time of the intermolecular compound having excellent electric characteristics (decay time) as a light modulating material is more easily obtained in the production method of Example 1 than in the production method of Comparative Example 1. In other words, it is clear that the production method of Example 1 is a method for producing an intermolecular compound suitable for producing a light control panel having better responsiveness.

It is a flowchart figure which illustrated the ultrasonic irradiation process when performing ultrasonic irradiation according to this invention.

Claims (2)

  Iodine (i), alkaline earth metal iodide (ii), and heterocyclic compound (iii) are combined in a solvent while irradiating ultrasonic waves, or the alkaline earth metal is irradiated with ultrasonic waves after the bonding. A method for producing an intermolecular compound comprising a periodate and a heterocyclic compound, comprising irradiating ultrasonic waves at a frequency of 20 to 30 kHz and an output of 100 to 2,000 W, comprising: an alkaline earth metal periodate and a heterocyclic compound. And a method for producing an intermolecular compound.   Ultrasonic irradiation is performed so that the temperature of a mixture of iodine (i), alkaline earth metal iodide (ii), heterocyclic compound (iii), and a solvent is 20 to 60 ° C. The method for producing an intermolecular compound according to claim 1.

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