JP2010260842A - Amorphous compound and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a stabilizer for polymers, which quickly dissolves in a hydrocarbon solvent. <P>SOLUTION: An amorphous compound is represented by formula (1) and has an endothermic peak at 15-25°C determined by differential scanning calorimetry (DSC) and a dissolution rate of 5 mg/sec or higher in cyclohexane at 25°C in the following test system: in the test system for solution rate, the measurement is carried out by loading a container (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm) containing 50 g of cyclohexane at 25°C with 3 g of a test substance; rotating fan type stirring blades with 38 mm diameter at a rotational speed of 100 rpm; and measuring the time taken for the test substance to be dissolved. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to an amorphous compound and a production method thereof.

The polymer stabilizer imparts stability to heat, light, oxygen and the like to a polymer such as a thermoplastic polymer (for example, polybutadiene), and is used by being contained in the polymer. As an active ingredient of the polymer stabilizer, a compound represented by the formula (1-1) is known, and it is also known that the compound can be obtained as a powdery crystal (for example, see Patent Document 1).

Japanese Patent Laid-Open No. 1-168643

  As an active ingredient of a polymer stabilizer, the ability to rapidly dissolve in a hydrocarbon solvent is required.

  Under such circumstances, the present inventors have intensively studied, and as a result, have reached the present invention.

（式中、Ｒ¹及びＲ²は、それぞれ独立に、水素原子、炭素数１〜８のアルキル基又は炭素数５〜８のシクロアルキル基を表し、Ｒ³ は水素原子又は炭素数１〜８のアルキル基を表す。Ｘは、単結合、硫黄原子、酸素原子、炭素数１〜８のアルキリデン基又は炭素数５〜８のシクロアルキリデン基を表す。）
で示され、示差走査熱量測定（ＤＳＣ）による吸熱ピークが１５〜２５℃であり、下記の試験系において２５℃でのシクロヘキサンに対する溶解速度が５ｍｇ／ｓｅｃ以上である非晶性化合物（以下、本発明非晶性化合物と記すこともある。）

＜溶解速度に係る試験系＞
２５℃で、５０ｇのシクロヘキサン入り容器（容量：１００ｍｌ、外径：５５ｍｍ、高さ：７０ｍｍ）に３ｇの被験物質を入れ、３８ｍｍ径ファン型攪拌翼を１００ｒｐｍの回転数で回転させ、前記被験物質が溶解するまでの時間を測定する。；
２． ＣｕＫαスペクトルを用いたＸ線回折測定において図２記載のＸ線回折パターンで示される原子配列状態であることを特徴とする前項１記載の非晶性化合物；
３． 式（１）において、Ｒ^１及びＲ^２がｔ−ペンチル基であり、Ｒ^３が水素原子であり、Ｘがエチリデン基であることを特徴とする前項１又は２記載の非晶性化合物；
４． 式（１）において、Ｒ^１がｔ−ブチル基であり、Ｒ^２がメチル基であり、Ｒ^３が水素原子であり、Ｘがメチレン基であることを特徴とする前項１又は２記載の非晶性化合物；
５． 式（１）

（式中、Ｒ¹及びＲ²は、それぞれ独立に、水素原子、炭素数１〜８のアルキル基又は炭素数５〜８のシクロアルキル基を表し、Ｒ³ は水素原子又は炭素数１〜８のアルキル基を表す。Ｘは、単結合、硫黄原子、酸素原子、炭素数１〜８のアルキリデン基又は炭素数５〜８のシクロアルキリデン基を表す。）
で示され、融点が７０℃〜２２０℃である結晶物質を融点以上の温度に加熱して融解する第１工程と、第１工程で得られた融解物を冷却及び固化する第２工程とを含むことを特徴とする前項１記載の非晶性化合物の製造方法；
等を提供するものである。 That is, the present invention
1. Formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
And an endothermic peak by differential scanning calorimetry (DSC) of 15 to 25 ° C., and a dissolution rate with respect to cyclohexane at 25 ° C. at 5 ° C. or more in the following test system (hereinafter referred to as the present compound). (Inventive amorphous compound may also be described.)

<Test system related to dissolution rate>
At 25 ° C., 3 g of the test substance is placed in a container containing 50 g of cyclohexane (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm), and a 38 mm fan-type stirring blade is rotated at a rotation speed of 100 rpm. Measure the time to dissolve. ;
2. 2. The amorphous compound according to item 1 above, which is in an atomic arrangement state indicated by an X-ray diffraction pattern shown in FIG. 2 in an X-ray diffraction measurement using a CuKα spectrum;
3. In the formula (1), R ¹ and R ² are t-pentyl groups, R ³ is a hydrogen atom, and X is an ethylidene group;
4). ^3. The non-represented item 1 or 2 above, wherein in the formula (1), R ¹ is a t-butyl group, R ² is a methyl group, R ³ is a hydrogen atom, and X is a methylene group. A crystalline compound;
5). Formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
A first step of melting a crystalline substance having a melting point of 70 ° C. to 220 ° C. by heating to a temperature higher than the melting point, and a second step of cooling and solidifying the melt obtained in the first step. A method for producing an amorphous compound according to item 1 above, comprising:
Etc. are provided.

  The amorphous compound of the present invention has excellent “performance to dissolve rapidly in a hydrocarbon solvent” and is extremely useful as an active ingredient of a polymer stabilizer.

FIG. 1 is a diagram showing an endothermic peak of the amorphous compound of the present invention in differential scanning calorimetry using DSC. Since the peak is a broad peak in phase transition, it is a diagram showing an amorphous atomic arrangement state.

FIG. 2 is a diagram showing an X-ray diffraction pattern of the amorphous compound of the present invention in an X-ray diffraction measurement using a CuKα spectrum. Since the pattern includes a broad peak, it can be confirmed that the pattern is in an amorphous atomic arrangement state.

FIG. 3 is a diagram showing an endothermic peak of a crystalline compound in differential scanning calorimetry using DSC. Since the peak is a sharp peak at one point in the melting point, it is a diagram showing a crystalline atomic arrangement state.

FIG. 4 is a diagram showing an X-ray diffraction pattern of a crystalline compound in X-ray diffraction measurement using a CuKα spectrum. It is a figure which shows that it is a crystalline atomic arrangement state from the said pattern including the sharp diffraction peak in each crystal lattice plane.

（式中、Ｒ¹及びＲ²は、それぞれ独立に、水素原子、炭素数１〜８のアルキル基又は炭素数５〜８のシクロアルキル基を表し、Ｒ³ は水素原子又は炭素数１〜８のアルキル基を表す。Ｘは、単結合、硫黄原子、酸素原子、炭素数１〜８のアルキリデン基又は炭素数５〜８のシクロアルキリデン基を表す。）
で示され、示差走査熱量測定（ＤＳＣ）による吸熱ピークが１５〜２５℃であり、下記の試験系において２５℃でのシクロヘキサンに対する溶解速度が５ｍｇ／ｓｅｃ以上である非晶性化合物

＜溶解速度に係る試験系＞
２５℃で、５０ｇのシクロヘキサン入り容器（容量：１００ｍｌ、外径：５５ｍｍ、高さ：７０ｍｍ）に３ｇの被験物質を入れ、３８ｍｍ径ファン型攪拌翼を１００ｒｐｍの回転数で回転させ、前記被験物質が溶解するまでの時間を測定する。
を含む。 The present invention relates to formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
An amorphous compound having an endothermic peak by differential scanning calorimetry (DSC) of 15 to 25 ° C. and a dissolution rate with respect to cyclohexane at 25 ° C. in the following test system of 5 mg / sec or more

<Test system related to dissolution rate>
At 25 ° C., 3 g of the test substance is placed in a container containing 50 g of cyclohexane (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm), and a 38 mm fan-type stirring blade is rotated at a rotation speed of 100 rpm. Measure the time to dissolve.
including.

In formula (1), R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms. Here, examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an i-pentyl group. , T-pentyl group, 2-ethylhexyl group and the like. Examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 3-methylcyclopentyl group, a 4-methylcyclopentyl group, and a 3-methylcyclohexyl group. Among them, for example, a methyl group, a t-butyl group, a t-pentyl group, and the like are preferable.

R ³ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Examples of the alkyl group for R ³ include the alkyl groups exemplified for R ¹ . Of these, a hydrogen atom or a methyl group is preferred.

X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.
Here, examples of the alkylidene group include a methylene group, an ethylidene group, a propylidene group, and a butylidene group. Examples of the cycloalkylidene group include a cyclopentylidene group and a cyclohexylidene group. Among these, a methylene group, an ethylidene group, or a butylidene group is preferable.

  Specific examples of the amorphous compound of the present invention include 2- [1- (2-hydroxy-3,5-di-t-pentylphenyl) ethyl] -4,6-di-t-pentylphenyl acrylate, 2,4-di-t-butyl-6- [1- (3,5-di-t-butyl-2-hydroxyphenyl) ethyl] phenyl acrylate, 2-t-butyl-6- (3-t-butyl -2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 2-t-butyl-6- [1- (3-t-butyl-2-hydroxy-5-methylphenyl) ethyl] -4-methyl Phenyl acrylate, 2-t-butyl-6- [1- (3-t-butyl-2-hydroxy-5-methylphenyl) propyl] -4-methylphenyl acrylate, 2-t-butyl-6- [1- (3-t Butyl-2-hydroxy-5-propylphenyl) ethyl] -4-propylphenyl acrylate, 2-t-butyl-6- [1- (3-t-butyl-2-hydroxy-5-isopropylphenyl) ethyl]- Examples include 4-isopropylphenyl acrylate.

Specific preferred non-crystalline compounds of the present invention include, for example, 2- [1- (2-hydroxy-3,5-di-t-pentylphenyl) ethyl] -4,6-di-t-pentylphenyl acrylate. That is, in the formula (1), R ¹ and R ² are t-pentyl groups, R ³ is a hydrogen atom, and X is an ethylidene group, or 2-t-butyl-6- (3- t-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, ie, in formula (1), R ¹ is a t-butyl group, R ² is a methyl group, and R ³ is hydrogen. Examples thereof include substances that are atoms and X is a methylene group.

  In the amorphous compound of the present invention, the endothermic peak by differential scanning calorimetry (DSC) is 15 to 25 ° C. In the amorphous compound of the present invention, at 25 ° C., 3 g of the test substance is placed in a container (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm) containing 50 g of cyclohexane, and a 38 mm fan fan stirring blade is placed at 100 rpm. In a “test system relating to dissolution rate”, which is measured by rotating at a rotational speed and measuring the time until the test substance is dissolved, the dissolution rate is 5 mg / sec or more, preferably 5 mg / sec or more and 9 mg / sec or less.

Examples of the amorphous compound of the present invention include substances that are in the atomic arrangement state shown by the X-ray diffraction pattern shown in FIG. 2 in X-ray diffraction measurement using a CuKα spectrum.
FIG. 2 shows the results of X-ray diffraction measurement with the vertical axis representing the peak intensity and the horizontal axis representing the diffraction line angle 2θ. As a preferred amorphous compound of the present invention, for example, the peak top 2θ is 10 to 12 ° and Examples thereof include an amorphous compound having a diffraction pattern having two broad peaks existing at 16 to 19 °. More preferably, an amorphous compound having a diffraction pattern having two broad peaks in which 2θ of the peak top exists at, for example, 10 to 11 ° and 16 to 18 ° can be used.

  Examples of the shape of the amorphous compound of the present invention include a granular shape and a plate shape, and a granular shape is preferable. Specific examples of the granular form include a pellet form, a granule form, a tablet form, a substantially spherical shape, a substantially hemispherical shape, and a flake shape, and a substantially spherical shape or a substantially hemispherical shape is preferable. In addition, the weight per grain of the granular amorphous compound of the present invention is preferably 1 mg or more of the amorphous compound of the present invention, more preferably 1 mg to about 25 mg. Examples of the particle diameter per one particle of the amorphous compound of the present invention include about 1 mm to about 6 mm. Especially, about 2 mm-about 5 mm are mentioned preferably. Moreover, as the height, about 1 mm-about 4 mm etc. can be mentioned, for example. Especially, about 1 mm-about 3 mm are mentioned preferably. In addition, the hardness of the granular amorphous compound of the present invention includes, for example, about 10N to about 30N.

  In addition, when the shape of the amorphous compound material of the present invention is a plate shape, it can be pulverized into a flake shape if necessary.

（式中、Ｒ¹及びＲ²は、それぞれ独立に、水素原子、炭素数１〜８のアルキル基又は炭素数５〜８のシクロアルキル基を表し、Ｒ³ は水素原子又は炭素数１〜８のアルキル基を表す。Ｘは、単結合、硫黄原子、酸素原子、炭素数１〜８のアルキリデン基又は炭素数５〜８のシクロアルキリデン基を表す。）
で示され、融点が７０℃〜２２０℃、好ましくは、１００〜１４０℃であり、１粒当りの重量が１ｍｇ未満の微粉末である結晶物質を融点以上の温度に加熱して融解する第１工程と、第１工程で得られた融解物を冷却及び固化する第２工程とを含むことを特徴とする製造方法を挙げることができる。 As a method for producing the amorphous compound of the present invention, for example, the formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
A melting point of 70 ° C. to 220 ° C., preferably 100 ° C. to 140 ° C., and a crystalline substance that is a fine powder having a weight per grain of less than 1 mg is heated to a temperature equal to or higher than the melting point to be melted. The manufacturing method characterized by including the process and the 2nd process of cooling and solidifying the melt obtained at the 1st process can be mentioned.

  In the first step of the method for producing an amorphous compound of the present invention, the crystalline substance may be melted by heating to a temperature higher than the melting point, and the “temperature higher than the melting point” is, for example, about 90 ° C. to about 250 ° C, preferably about 120 ° C to about 160 ° C.

  In the second step in the method for producing an amorphous compound of the present invention, the melt obtained in the first step may be cooled and solidified. The temperature and time of “cooling” is, for example, about 50 ° C. or less. Examples include 10 seconds or more. Among these, about 0 ° C. to about 50 ° C. for about 10 seconds to about 2 minutes is preferable, and about 0 ° C. to about 40 ° C. for about 20 seconds to about 2 minutes is more preferable.

  As the second step of cooling and solidifying the melt obtained in the first step, for example, a heat exchange plate (for example, a sheet made of a metal such as stainless steel) cooled from the melt obtained in the first step. Spraying or dripping onto the cooled belt, for example, a method of dripping the melt obtained in the first step into cooled water or a poor solvent, for example, the melt obtained in the first step onto the cooled belt This can be accomplished by a continuous extrusion method.

As a method of dripping the melt, for example, a method of dripping from a dripping pipe, specifically, for example, a method of dripping after filling the melt into a roll drop granulator, a rotfoam granulator, etc. Can be mentioned.
Here, the roll drop granulator usually has a rotating drum having a protrusion, and the melt is scraped off at the tip of the protrusion, and the centrifugal force obtained by rotating the rotating drum and It is a granulator having a mechanism for dropping the melt on the heat exchange plate by the action of gravity. In addition, the rotfoam type granulator usually has a cylindrical portion, the cylindrical portion has a hole, and has a structure for receiving a melt inside the cylindrical portion. It is a granulator having a mechanism for dropping the melt on a heat exchange plate. In particular, dropping by a rotfoam type granulator is preferable.

  In addition, in order to control the weight per one grain of the amorphous compound of the present invention to a desired value, in the method of dropping the melt from the dropping tube, the diameter of the dropping tube, the viscosity of the melt, etc. are adjusted. Thus, the amount of dripping may be controlled from the dripping tube of the melt. Specifically, for example, in the case of a roll drop granulator, the amount of melted material scraped off at the tip of the protrusion may be controlled. The amount of dripping may be controlled from the dripping tube of the melt by adjusting the viscosity of the melt.

  Examples of the “cooled heat exchange plate” include a heat exchange plate adjusted to about 0 ° C. to about 50 ° C. Specifically, for example, a stainless steel belt heated to a predetermined temperature with water, a stainless steel belt heated to a predetermined temperature with cold air, a stainless steel plate heated to a predetermined temperature with water, etc. And stainless steel plate. In addition, it is preferable that the surface of the heat exchange plate on which the melt is dropped is smooth.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples.
As a crystalline substance represented by the formula (1) and having a melting point of 100 ° C. to 140 ° C. and a weight of less than 1 mg per grain, 2- [1- (2-hydroxy-3,5- Di-t-pentylphenyl) ethyl] -4,6-di-t-pentylphenyl acrylate (melting point: 115 ° C., manufactured by Sumitomo Chemical Co., Ltd.) (hereinafter sometimes referred to as compound (1)) and 2-t -Butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate (melting point 130 ° C., manufactured by Sumitomo Chemical Co., Ltd.) (hereinafter may be referred to as compound (2)) .) Was used.

Example 1
Compound (1) was poured into a melting tank heated to 145 ° C. and melted. Next, the obtained melt was dropped on a stainless steel plate cooled with 30 ° C. cooling water, and then cooled and solidified on the stainless steel plate for 25 seconds to obtain a substantially hemispherical amorphous compound. . The obtained amorphous compound had a particle size (width): 3.4 mm, a height: 2.2 mm, a weight of 8.62 mg / piece, and a hardness of 24.79 N. .
Next, the obtained amorphous compound was subjected to the following DSC analysis, XRD analysis, dissolution rate measurement and the like.

(DSC analysis)
The obtained amorphous compound was sealed in an aluminum cell using a differential scanning calorimeter DSC-60A manufactured by Shimadzu Corporation. After the aluminum cell was inserted into a sample holder provided in the differential scanning calorimeter, an endothermic peak was observed while heating the sample holder to 150 ° C. at a rate of 10 ° C./min in a nitrogen atmosphere.
As a result, as shown in FIG. 1, the endothermic peak of the obtained amorphous compound was 23.7 ° C.

(XRD analysis)
The obtained amorphous compound was pulverized. Next, the obtained pulverized product was inserted into a sample holder provided in a RINT2000 vertical goniometer manufactured by Rigaku Corporation, and then an X-ray diffraction pattern in X-ray diffraction measurement was measured using a CuKα spectrum. The obtained X-ray diffraction pattern is shown in FIG.
As a result, as shown in FIG. 2, since the pattern includes a broad peak, it was confirmed that it was in an amorphous atomic arrangement state.

(Weight measurement per granular amorphous compound)
Using a precision balance manufactured by METTLER TOLEDO, the weight of each obtained amorphous compound was measured. The measurement was repeated 20 times, and the average value was defined as “weight per granular amorphous compound”.

(Measurement of hardness of granular amorphous compound)
The hardness of the obtained amorphous compound was measured as follows using a digital force gauge FGP-5 manufactured by SHIMPO. The measurement was repeated 20 times, and the average value was defined as “the hardness of the granular amorphous compound”.
A sample stage equipped with a measuring instrument was placed on the obtained amorphous compound. A pressure was applied to the amorphous compound by lowering the tip of the probe attached to the measuring instrument to the position of the amorphous compound on the sample stage. The scale of the crushing pressure gauge when the amorphous compound was crushed was read, and this was defined as “the hardness of the granular amorphous compound”.

(Measurement of particle size (width) and height of granular amorphous compound)
Using a caliper, the particle size (width) and height of the obtained amorphous compound were measured. The measurement was repeated 10 times, and the average values were defined as “particle size (width) of granular amorphous compound” and “height of granular amorphous compound”.

(Dissolution rate measurement)
At 25 ° C., 3 g of the test substance is placed in a container containing 50 g of cyclohexane (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm), and a 38 mm fan-type stirring blade is rotated at a rotation speed of 100 rpm. The time until it dissolved was measured. The results are shown in Table 1 as dissolution rates expressed in “mg / sec” units.

(Example 2)
Instead of the “compound (1)” used in Example 1, a “mixture obtained by mixing the compound (1) and the compound (2) at a weight ratio of 99.5: 0.5” was used. In accordance with the same method as in Example 1, a semispherical solid amorphous compound was obtained. The obtained amorphous compound had a particle size (width): 3.1 mm, a height: 1.8 mm, a weight of 9.65 mg / piece, and a hardness of 23.77 N. .
Next, the obtained amorphous compound was subjected to the above DSC analysis, XRD analysis, dissolution rate measurement and the like.

(Example 3)
Example 1 is used except that “compound (1) and compound (2) are mixed in a weight ratio of 95: 5” instead of “compound (1)” used in Example 1. According to the same method, a semispherical solid amorphous compound was obtained. The obtained amorphous compound had a particle size (width): 2.7 mm, a height: 1.7 mm, a weight of 9.99 mg / piece, and a hardness of 23.19 N. .
Next, the obtained amorphous compound was subjected to the above DSC analysis, XRD analysis, dissolution rate measurement and the like.

(Comparative Example 1)
DSC analysis, XRD analysis, and dissolution rate measurement according to the same method as above except that compound (1) is used as it is instead of “compound (1)” instead of “obtained amorphous compound” Etc.
The results are shown in FIG. 3 (DSC analysis) and FIG. 4 (XRD analysis) and Table 1 (weight, hardness, particle size (width) and height, dissolution rate).

  The amorphous compound of the present invention has excellent “performance to dissolve rapidly in a hydrocarbon solvent” and is extremely useful as an active ingredient of a polymer stabilizer.

Claims (5)

Formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
An amorphous compound having an endothermic peak by differential scanning calorimetry (DSC) of 15 to 25 ° C. and a dissolution rate with respect to cyclohexane at 25 ° C. in the following test system is 5 mg / sec or more.

<Test system related to dissolution rate>
At 25 ° C., 3 g of the test substance is placed in a container containing 50 g of cyclohexane (capacity: 100 ml, outer diameter: 55 mm, height: 70 mm), and a 38 mm fan-type stirring blade is rotated at a rotation speed of 100 rpm. Measure the time to dissolve. 2. The amorphous compound according to claim 1, wherein the amorphous compound is in an atomic arrangement state indicated by an X-ray diffraction pattern shown in the following figure in an X-ray diffraction measurement using a CuKα spectrum.

In Formula (1), R < ¹ > and R < ² > is a t-pentyl group, R < ³ > is a hydrogen atom, X is an ethylidene group, The amorphous compound of Claim 1 or 2 characterized by the above-mentioned. The formula (1), wherein R ¹ is a t-butyl group, R ² is a methyl group, R ³ is a hydrogen atom, and X is a methylene group. Amorphous compound. Formula (1)

(Wherein, R ¹ and R ² each independently represent a hydrogen atom, an alkyl group or a cycloalkyl group having a carbon number of 5-8 having from 1 to 8 carbon atoms, R ³ is 1-8 hydrogen atoms or carbon atoms X represents a single bond, a sulfur atom, an oxygen atom, an alkylidene group having 1 to 8 carbon atoms, or a cycloalkylidene group having 5 to 8 carbon atoms.)
A first step of melting a crystalline substance having a melting point of 70 ° C. to 220 ° C. by heating to a temperature equal to or higher than the melting point, and a second step of cooling and solidifying the melt obtained in the first step. The method for producing an amorphous compound according to claim 1, comprising:

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