WO2021065653A1 - Poudre, procédé de production de poudre et procédé de production de solution - Google Patents

Poudre, procédé de production de poudre et procédé de production de solution Download PDF

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Publication number
WO2021065653A1
WO2021065653A1 PCT/JP2020/035950 JP2020035950W WO2021065653A1 WO 2021065653 A1 WO2021065653 A1 WO 2021065653A1 JP 2020035950 W JP2020035950 W JP 2020035950W WO 2021065653 A1 WO2021065653 A1 WO 2021065653A1
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powder
bis
less
general formula
temperature
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PCT/JP2020/035950
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English (en)
Japanese (ja)
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健史 細井
峰男 渡辺
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セントラル硝子株式会社
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Priority to CN202080068632.5A priority Critical patent/CN114555549A/zh
Priority to KR1020227013503A priority patent/KR20220069060A/ko
Priority to JP2021550673A priority patent/JPWO2021065653A1/ja
Publication of WO2021065653A1 publication Critical patent/WO2021065653A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention relates to a powder, a method for producing a powder, and a method for producing a solution. More specifically, the present invention relates to a powder of a fluorinated bisphenol compound represented by the general formula (A) described later, a method for producing the powder, and a method for producing a solution using the powder.
  • BIOS-AF 2,2-bis (4-hydroxyphenyl) hexafluoropropane
  • Patent Document 1 which is a document relating to an epoxy resin composition, as Production Example 1, BIS-AF was crystallized in a mixed solvent of ethylene glycol and pure water to obtain a white powder thereof. It is stated that.
  • Patent Document 2 a solid BIS-AF in which the impurity hexafluoroacetone is reduced by neutralizing and precipitating BIS-AF dissolved in an alkaline aqueous solution with hydrochloric acid is used. It is stated that it was obtained.
  • Fluorinated bisphenol compounds typified by BIS-AF are industrially usually manufactured and sold as powders.
  • the powder may be used as it is in various industrial processes.
  • "Industrial handleability" means, for example, one or more of the following items. ⁇ Good filterability ⁇ Short drying time when drying wet powder ⁇ Difficult to absorb moisture ⁇ Good fluidity of powder ⁇ Good solvent solubility, specifically, quick dissolution in solvent ⁇ Agglomeration Difficult to (block)
  • the present invention has been made in view of such circumstances.
  • One of the objects of the present invention is to provide a powdery fluorinated bisphenol compound having excellent industrial handleability.
  • the present inventors have completed the following first to fourth inventions.
  • the first invention is as follows.
  • the mode diameter D m measured by the laser diffraction / scattering method is 75 to 150 ⁇ m.
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • the second invention is as follows.
  • a powder of a compound represented by the general formula (A) below is a powder of 1.1 to 1.5.
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • the third invention is as follows.
  • a powder of a compound represented by the general formula (A) below Volume-reduced cumulative 50% diameter D 50 measured by a laser diffraction scattering method is 50 ⁇ 100 [mu] m, A powder with an angle of repose of 35 to 49 °.
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • the fourth invention is as follows.
  • a method for producing a powder of a compound represented by the general formula (A) By putting the raw material containing the compound represented by the general formula (A) and the aqueous dispersion medium in a container and heating the raw material, the raw material is melted in the presence of the aqueous dispersion medium, and the raw material is melted.
  • the melting temperature T 1 of the said raw material, said aqueous dispersion medium, the solubility of the compound represented by the general formula (A), 10 [g / 100g] or less the production of the powder Method.
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • a method for producing a solution containing a compound represented by the general formula (A) below comprises a step of obtaining a solution of the compound represented by the general formula (A) using a solvent and at least one of the powders of the first to fourth inventions.
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • the powder of the present invention is excellent in industrial handleability.
  • XY in the description of the numerical range means X or more and Y or less unless otherwise specified.
  • X to 5% by mass means "1% by mass or more and 5% by mass or less”.
  • the notation that does not indicate whether it is substituted or unsubstituted includes both those having no substituent and those having a substituent.
  • the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the term "electronic device” as used herein refers to an element to which electronic engineering technology is applied, such as a semiconductor chip, a semiconductor element, a printed wiring board, an electric circuit display device, an information communication terminal, a light emitting diode, a physical battery, and a chemical battery. , Devices, final products, etc.
  • compound (A) the compound represented by the general formula (A) may be referred to as "compound (A)".
  • the embodiment of the first invention is the first embodiment
  • the embodiment of the second invention is the second embodiment
  • the embodiment of the third invention is the third embodiment
  • the embodiment of the fourth invention May be referred to as the fourth embodiment.
  • the embodiment of the above-mentioned powder manufacturing method invention may be described as the first manufacturing method.
  • a method for producing a powder that does not correspond to the above-mentioned invention of the powder production method but can produce the powder of the present invention (at least one of the first to fourth inventions) is described as a second production method.
  • the powders of the first to third embodiments are powders of a compound (compound (A)) represented by the following general formula (A). Further, the powder of the fourth embodiment is a powder of a compound in which all of R 1 to R 8 are hydrogen atoms in the following general formula (A).
  • R 1 to R 8 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or an amino group, respectively.
  • R 1 to R 8 are independently hydrogen atoms or amino groups.
  • R 1 to R 8 when at least one of R 1 to R 8 is a group other than a hydrogen atom, the group other than the hydrogen atom is at any position of R 2 , R 3 , R 6 , or R 7. It is preferable to be present in. This is because of the ease of synthesizing the compound.
  • 0 to 4 of R 1 to R 8 are preferably groups other than hydrogen atoms, and 0 to 2 are more preferably groups other than hydrogen atoms.
  • the compound (A) includes 2,2 bis (4-hydroxyphenyl) hexafluoropropane, 2,2-bis (4-hydroxy-3-methylphenyl) hexafluoropropane, and 2,2-bis (3).
  • -Ethyl-4-hydroxyphenyl) hexafluoropropane 2,2-bis (4-hydroxy-3,5-dimethylphenyl) hexafluoropropane, 2,2-bis (3-fluoro-4-hydroxyphenyl) hexafluoro Propane, 2,2-bis (3-bromo-4-hydroxyphenyl) hexafluoropropane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) hexafluoropropane, 2,2-bis (3-bis) Amino-4-hydroxyphenyl) hexafluoropropane and the like can be mentioned.
  • the mode diameter (mode diameter) D m of the powder of the first embodiment measured by the laser diffraction / scattering method is 75 to 150 ⁇ m, preferably 75 to 135 ⁇ m, and more preferably 75 to 120 m.
  • the Ca ion content of the powder of the first embodiment is less than 1 ppm, preferably 0.7 ppm or less, and more preferably 0.5 ppm or less.
  • the "ppm" of the Ca ion (and Na ion described later) content is one million of "mass of Ca ion in powder / mass of powder". It is a fraction.
  • the industrial handleability of the powder of the first embodiment is good.
  • the powder of the first embodiment has advantages such as "good filterability" and "the drying time when drying the wet powder can be shortened". It is presumed that these advantages are due to the D m being 75 to 150 ⁇ m. The details are unknown, but it is presumed that when the D m is 75 ⁇ m or more, there is an appropriate “gap” between the particles, which makes it easier for the liquid to flow. Further, it is presumed that when D m is 150 ⁇ m or less, the “gap” does not become too large, and it is difficult to hold a large amount of liquid between the particles in the first place.
  • the present inventors have tried to control the content of Ca ions in the powder to less than 1 ppm in the first embodiment.
  • Ca ion is a component inevitably contained in general industrial water. Therefore, if the powder of compound (A) is produced so that the content of Ca ions is less than 1 ppm using the content of Ca ions as an index, various trace impurities (industrial water) other than Ca ions in the obtained powder can be produced. The amount of origin) can also be reduced. That is, the compound (A) in which the amount of Ca ions is less than 1 ppm is considered to have a small amount of not only Ca ions but also various impurities, and is preferably applicable to various technical fields. In addition, as will be described later, since Ca ions can be measured by ion chromatography, it is possible to facilitate process control in mass production equipment.
  • the fact that the Ca ion content is less than 1 ppm means that the powder of the first embodiment can be directly used preferably as a material for manufacturing an electronic device that requires a small amount of metal ions. Means.
  • the Ca ion content is preferably 0.7 ppm or less, more preferably 0.5 ppm or less. Basically, the smaller the amount of Ca ions, the more preferable.
  • the Ca ion content may be zero (below the measurement limit of the device). From a practical point of view, the Ca ion content is, for example, 0.01 ppm or more.
  • the method and conditions for producing the powder of the first embodiment are not limited. By selecting appropriate methods and conditions, a powder of compound (A) having a D m of 75 to 150 ⁇ m and a Ca ion content of less than 1 ppm can be obtained. Preferably, as in the first production method described later, it is preferable that the raw material is melted (not dissolved) in an aqueous dispersion medium and then crystallized. By appropriately selecting the conditions for melting and crystallization, a powder of compound (A) having a D m of 75 to 150 ⁇ m and a Ca ion content of less than 1 ppm can be obtained. The manufacturing method and manufacturing conditions will be described in detail later.
  • the Na ion content of the powder of the first embodiment is less than 1 ppm, preferably 0.7 ppm or less, and more preferably 0.5 ppm or less.
  • the powder of the present embodiment can be further more preferably applied to the production of electronic devices.
  • the Na ion content may be zero (below the measurement limit of the device). From a practical point of view, the Na ion content is, for example, 0.01 ppm or more.
  • the content of Mg ions in the powder of the first embodiment is less than 1 ppm, preferably 0.7 ppm or less, and more preferably 0.5 ppm or less.
  • the content of Mg ions is also an index that can be used when calculating the hardness of water, and Mg ions may be unavoidably contained in industrial water. Therefore, by setting the amount of Mg ions in addition to Ca ions to less than 1 ppm, the powder of the present embodiment can be further more suitably applied to various uses such as manufacturing of electronic devices. Further, the content of Mg ions may be zero (below the measurement limit of the apparatus). From a practical point of view, the content of Mg ions is preferably 0.01 ppm or more, for example.
  • the content of metal ions such as Ca ions can be determined by using an ion chromatography analysis method.
  • ion chromatography analysis a sample solution in which the powder of compound (A) is usually dissolved in an organic solvent such as t-butyl methyl ether is prepared. The content of metal ions in this sample liquid is measured, and "mass of Ca ions in powder / mass of powder" is calculated from the obtained measured values.
  • a metal such as Ca ion is formed by recrystallizing the compound (A) by a method of "not actively” dissolving "the compound (A) in water while using water as in the first manufacturing method described later. A powder having a small amount of ions can be obtained.
  • the powder of the first embodiment does not contain alcohol such as monool and diol, or preferably contains a small amount of alcohol.
  • Alcohol such as monool and diol, or preferably contains a small amount of alcohol.
  • Water-soluble monools with 4 or less carbon atoms such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 2-butanol, 2-methyl, even if they contain alcohol. It is more preferable to contain a small amount of -2-propanol or the like.
  • the content of alcohol in the powder of the first embodiment is preferably 400 ppm or less, more preferably 200 ppm or less, still more preferably 100 ppm or less.
  • alcohol does not include phenolic compounds (compounds having phenolic hydroxyl groups). Since the powder does not contain alcohol, or even if it contains a small amount of alcohol, an unintended reaction is unlikely to occur when a polymer is produced using the powder of the present embodiment as a raw material, and a desired polymer can be obtained. Easy to manufacture. Further, since the compound (A) and the alcohol can be hydrogen-bonded, it is easy to accurately weigh the amount of the pure compound (A) when the powder does not contain alcohol or even if it contains a small amount of alcohol. There are advantages. This means that, for example, the "equivalent ratio" when the compound (A) and the epoxy compound are reacted can be accurately controlled, and the physical properties of the finally obtained resin can be easily controlled.
  • Patent Document 1 since ethylene glycol is used for purification of BIS-AF, it is considered that BIS-AF described in Patent Document 1 contains ethylene glycol of more than 400 ppm.
  • alcohol may be used as a part of the dispersion medium for dispersing the compound (A).
  • the amount of alcohol in the powder is small because the compound (A) is not positively “dissolved” in alcohol. Further, when only water is used as the dispersion medium, the compound (A) does not contain alcohol in principle.
  • the amount of alcohol in compound (A) can be determined using, for example, a gas chromatograph.
  • D 50 When the volume-based cumulative 50% diameter of the powder of the first embodiment measured by the laser diffraction / scattering method is D 50 , D 50 is preferably 40 to 100 ⁇ m, more preferably 40 to 90 ⁇ m, and further preferably 40. It is ⁇ 80 ⁇ m.
  • the powder of the first embodiment can be more easily handled when D 50 is within a specific numerical range. It is considered that when D 50 is relatively large, the contact area between the particles becomes smaller and the friction between the particles during flow becomes smaller. And it is considered that it leads to further improvement of filterability and dryness.
  • the value of (D 90- D 50 ) / D 50 is preferably 1.3 to 1. It is 1.7, more preferably 1.4 to 1.7.
  • the index (D 90- D 50 ) / D 50 can be said to be an index indicating the degree of spread of the "hem" on the large particle size side in the particle size distribution curve. When this value is 1.7 or less, it means that the particle size distribution on the large particle size side is relatively sharp. It is considered that the sharp particle size distribution enhances the homogeneity of the powder and further enhances the handleability.
  • (D 90- D 50 ) / D 50 is 1.7 or less is considered to mean that the number of coarse particles is relatively small. With a relatively small number of coarse particles, for example, agglomeration may be suppressed.
  • 1.3 which is the lower limit of the preferable range of (D 90- D 50 ) / D 50 , sets a range in which the cost and labor of recrystallization when obtaining the powder of the compound (A) are not excessive. It was done.
  • the value of (D 90- D m ) / D m is preferably 0.93 or less, more preferably 0.92 or less.
  • the lower limit of the value of (D 90- D m ) / D m is, for example, 0.40 or more.
  • D ave when the average diameter measured by a laser diffraction scattering method was D ave, D ave is preferably 45 ⁇ 80 [mu] m, more preferably 45 ⁇ 60 [mu] m.
  • the powder of the first embodiment tends to have a larger average diameter than the powder of the conventional compound (A) as a major tendency.
  • various values related to the particle size such as D m and D 50 can be obtained from the volume-based particle size distribution curve measured by the laser diffraction / scattering method.
  • a particle size distribution meter "SALD" series manufactured by Shimadzu Corporation can be mentioned as an apparatus capable of measuring by the laser diffraction / scattering method.
  • SALD particle size distribution meter
  • the measurement is usually carried out in a wet manner by dispersing the powder in a solvent that is substantially insoluble (for example, n-decane).
  • D 50 is 50 ⁇ m or more, that is, 50% or more of relatively large particles having a particle size of 50 ⁇ m or more on a volume basis are contained in the powder. It is presumed that the friction is small.
  • D 50 / D ave is 1.1 or more means that the shape of the particle size distribution curve in which the frequency is plotted on the vertical axis and the particle size is plotted on the horizontal axis is as shown in FIG.
  • the solvent solubility of the powder of the second embodiment is good. That is, surprisingly, the powder of the present embodiment, despite having a relatively large D 50, soluble relatively quickly in the solvent. The inventors speculate that the reason for this is that the small number of small particle particles in the powder suppresses the swelling and aggregation of BIS-AF in the solvent (swelling). When or agglomeration occurs, the dispersibility of the powder decreases and the dissolution rate is presumed to slow down).
  • the upper limit value of D 50 100 ⁇ m, is set to a range in which the cost and labor of recrystallization when obtaining the powder of the compound (A) are not excessive.
  • the method and conditions for producing the powder of the second embodiment are not limited. However, in order to obtain a powder of compound (A) having a D 50 of 50 to 100 ⁇ m and a D 50 / D ave of 1.1 to 1.5, it is preferable to select appropriate methods and conditions. In the present embodiment, for example, when the powder of the compound (A) is obtained by recrystallization, it is preferable to use a specific organic solvent, use a seed crystal, or slowly cool the powder. By selecting an appropriate production method and production conditions, a powder of compound (A) having a D 50 of 50 to 100 ⁇ m and a D 50 / D ave of 1.1 to 1.5 can be obtained. A specific manufacturing method will be described later as a "second manufacturing method". As a reminder, in producing the powder of the second embodiment, the first production method may be adopted.
  • D 50 is 50 to 100 ⁇ m, and D 50 / D ave is 1.1 to 1.5.
  • D 50 is preferably 50 to 90 ⁇ m, more preferably 50 to 80 ⁇ m, and even more preferably 50 to 70 ⁇ m.
  • D 50 / D ave is preferably 1.1 to 1.4, more preferably 1.1 to 1.3.
  • the fluidity can be further improved by setting the mode diameter (mode diameter) D m measured by the laser diffraction / scattering method within a specific numerical range. It is considered that when D m is relatively large, the contact area between the particles becomes smaller and the friction between the particles during flow becomes smaller. And it is considered that the handleability is further improved.
  • D m is preferably 75 to 150 ⁇ m, more preferably 80 to 120 ⁇ m.
  • the value of (D 90- D 50 ) / D 50 is preferably 1.3 to 1. It is 1.7, more preferably 1.4 to 1.7.
  • the index (D 90- D 50 ) / D 50 can be said to be an index showing the degree of spread of the "hem" on the right side (large particle size side) in the particle size distribution curve.
  • (D 90- D 50 ) / D 50 is 1.7 or less means that the particle size distribution on the large particle size side is relatively sharp, and from a different point of view from D 50 / D ave, the powder It is considered to mean that the particle size distribution deviates from the normal distribution as shown in FIG. Therefore, in addition to the fact that D 50 / D ave is 1.1 to 1.5, it is considered that the handleability is further improved by the fact that (D 90- D 50 ) / D 50 is 1.7 or less. .. Further, the fact that (D 90- D 50 ) / D 50 is 1.7 or less is considered to mean that the number of coarse particles is relatively small.
  • D 50 , D 90 , D ave and D m can be obtained from the volume-based particle size distribution curve measured by the laser diffraction / scattering method.
  • a particle size distribution meter "SALD" series manufactured by Shimadzu Corporation can be mentioned. The measurement is usually carried out in a wet manner by dispersing the powder in a solvent that is substantially insoluble (for example, n-decane).
  • a solvent that is substantially insoluble for example, n-decane
  • the handleability of the powder can be further improved.
  • the looseness density of the powder of the second embodiment is preferably 0.50 to 0.75 g / cm 3 , and more preferably 0.60 to 0.75 g / cm 3 .
  • the firmness density of the powder of the present embodiment is preferably 0.76 to 0.90 g / cm 3 , and more preferably 0.80 to 0.90 g / cm 3 .
  • D 50 is 50 ⁇ 100 [mu] m.
  • D 50 is preferably 50 to 90 ⁇ m, more preferably 50 to 80 ⁇ m, and even more preferably 50 to 70 ⁇ m.
  • the fluidity can be further improved by setting the mode diameter (mode diameter) D m measured by the laser diffraction / scattering method within a specific numerical range. It is considered that when D m is relatively large, the contact area between the particles becomes smaller and the friction between the particles during flow becomes smaller. And it is considered that the handleability is further improved.
  • D m is preferably 75 to 150 ⁇ m, more preferably 80 to 120 ⁇ m.
  • the value of (D 90- D 50 ) / D 50 is preferably 1.3 to 1. It is 1.7, more preferably 1.4 to 1.7.
  • the index (D 90- D 50 ) / D 50 can be said to be an index indicating the degree of spread of the "hem" on the large particle size side in the particle size distribution curve. When this value is 1.7 or less, it means that the particle size distribution on the large particle size side is relatively sharp. It is considered that the sharp particle size distribution enhances the homogeneity of the powder and further enhances the handleability.
  • (D 90- D 50 ) / D 50 is 1.7 or less is considered to mean that the number of coarse particles is relatively small. With a relatively small number of coarse particles, for example, agglomeration may be further suppressed.
  • 1.3 which is the lower limit of the preferable range of (D 90- D 50 ) / D 50 , sets a range in which the cost and labor of recrystallization when obtaining the powder of the compound (A) are not excessive. It was done.
  • D 50 , D 90 and D m can be obtained from the volume-based particle size distribution curve measured by the laser diffraction / scattering method.
  • a particle size distribution meter "SALD" series manufactured by Shimadzu Corporation can be mentioned. The measurement is usually carried out in a wet manner by dispersing the powder in a solvent that is substantially insoluble (for example, n-decane).
  • the angle of repose of the powder of the third embodiment is 35 to 49 °.
  • the angle of repose is preferably 40 to 49 °, more preferably 40 to 47 °.
  • For the method of measuring the angle of repose refer to the description of the examples below.
  • the handleability of the powder can be further improved.
  • the looseness density ⁇ 1 of the powder of the third embodiment is preferably 0.50 to 0.75 g / cm 3 , and more preferably 0.60 to 0.75 g / cm 3 .
  • the firmness density ⁇ 2 of the powder of the third embodiment is preferably 0.76 to 0.90 g / cm 3 , and more preferably 0.80 to 0.90 g / cm 3 .
  • ⁇ 2 / ⁇ 1 is preferably in the range of 1.01 to 1.45, and more preferably in the range of 1.10 to 1.40.
  • ⁇ 2 / ⁇ 1 is 1.45 or less, for example, when the powder of the present embodiment is weighed, the fluctuation of the mass to be weighed can be sufficiently reduced.
  • the powder of the fourth embodiment has advantages such as "fast dissolution rate in a solvent, particularly a polar solvent or an alkaline solvent” and "the drying time when drying a wet powder can be shortened”.
  • advantages such as "fast dissolution rate in a solvent, particularly a polar solvent or an alkaline solvent” and "the drying time when drying a wet powder can be shortened”.
  • An example of the measurement conditions is as follows.
  • Tube Cu Voltage: 40kV Current: 50mA
  • Solar slit 2.5 ° (incident side, light receiving side)
  • Scan range 10-80 ° Step width: 0.01 °
  • Scan speed 35 ° / min
  • Detector 1-dimensional X-ray detector (D / tex Ultra250; manufactured by Rigaku Co., Ltd.)
  • the method and conditions are not limited.
  • a powder in the range can be preferably obtained.
  • the particle size of the powder of the fourth embodiment is not particularly limited, and it is sufficient that the powder has an appropriate handleability.
  • the volume-based cumulative 50% diameter (D 50 ) measured by the laser diffraction / scattering method may be preferably 20 to 100 ⁇ m.
  • the lower limit may be more preferably 30 ⁇ m or more, further preferably 40 ⁇ m or more, and the upper limit may be more preferably 90 ⁇ m or less, further preferably 80 ⁇ m or less.
  • SALD particle size distribution meter
  • the measurement is usually carried out in a wet manner by dispersing the powder in a solvent that is substantially insoluble (for example, n-decane).
  • the powders of the first to fourth embodiments can be produced through an appropriate production method.
  • two preferable production methods first production method and second production method for producing the powders of the first to fourth embodiments will be described.
  • the method for producing a powder of a compound represented by the general formula (A) (first production method) is, for example, -By putting the raw material containing the compound represented by the general formula (A) and the aqueous dispersion medium in a container and heating the raw material, the raw material is melted in the presence of the aqueous dispersion medium, and the melted product of the raw material is obtained.
  • a melting step to obtain a heterogeneous liquid containing an aqueous dispersion medium ⁇ Crystallization process to obtain crystals by crystallizing the melt by lowering the temperature of the non-uniform liquid, Can be included.
  • the lower limit of this solubility may be zero, but the solubility is usually 0.5 [g / 100 g] or more.
  • Melting temperature T 1 of raw material means the lowest temperature at which all powdered (solid) raw material melts and loses its original form.
  • the fact that all the raw material has melted is (i) a method of visually observing the state of the raw material in the container and confirming that no powdery (solid) raw material is found, (ii) from inside the container. It can be confirmed by a method of quickly visually observing the extracted aqueous layer and confirming that the raw material does not remain in the powder form (solid form).
  • the first manufacturing method can also be described as follows.
  • -In the melting step the raw material containing the compound (A) is heated in an aqueous dispersion medium and melted (not melted) at a temperature T 1 to obtain a melt.
  • Aqueous dispersion medium Briefly, a compound at the temperature T 1 (A) "poor solvent” in the (unlikely liquid by dissolving the compound (A)).
  • T 1 a compound at the temperature T 1 (A) "poor solvent” in the (unlikely liquid by dissolving the compound (A)).
  • a heterogeneous liquid containing a melt of the raw material and an aqueous dispersion medium can be obtained.
  • the melt in the non-uniform liquid is crystallized.
  • the amount of Ca ions and the like can be reduced by moving Ca ions and the like from the raw material material side to the aqueous dispersion liquid side at the interface between the melt of the raw material and the aqueous dispersion. This is preferable from the viewpoint of producing the powder of the first embodiment (less Ca ions).
  • the raw material since the raw material is not positively “dissolved” (it does not go through a state in which the solute and the solvent are completely and uniformly mixed), Ca ions and the like, which are impurities derived from the solvent such as water, etc. However, it is considered that the raw material is suppressed from being incorporated into the recrystallized substance. Similarly, it is considered that Ca ions and the like, which are impurities once dissolved from the raw material, are suppressed from being "re-incorporated” into the crystallized raw material. These are also considered to be related to the fact that the amount of impurities such as Ca ions can be reduced.
  • BIS-AF by itself does not melt when heated to 100 ° C. (boiling point of water), but BIS-AF in water melts when heated to 100 ° C. (or lower temperature).
  • BIS-AF in water melts when heated to 100 ° C. (or lower temperature).
  • the melting point of BIS-AF is lowered by hydration.
  • Patent Document 3 For known information, refer to, for example, the above-mentioned Patent Document 3.
  • the first manufacturing method also has the additional advantage of having a small environmental load. Specifically, in carrying out the first production method, an aqueous dispersion is mainly used, and an organic solvent (a good solvent of compound (A)) is unnecessary. That is, by adopting the above manufacturing method, the use of organic solvent can be reduced, so that the environmental load can be reduced.
  • an organic solvent a good solvent of compound (A)
  • the -Melting step Normally, in the melting step, the raw material containing the compound (A) and the aqueous dispersion medium are heated in a container equipped with a stirring means and a heating means. By doing so, a heterogeneous liquid containing a melt of the raw material and an aqueous dispersion medium can be obtained. By heating with stirring, the non-uniform liquid usually becomes a suspended liquid. When agitated or stopped and allowed to stand, the non-uniform liquid is usually in a two-layer separated state.
  • the aqueous dispersion can contain substantially only water.
  • the amount of alcohol in the finally obtained compound (A) can be made substantially zero.
  • the solubility of the compound (A) in water is very small, there is an advantage that the amount of the compound (A) contained in the waste liquid can be reduced.
  • the aqueous dispersion can include water and alcohol.
  • the ratio of alcohol in the aqueous dispersion medium is usually 30% by mass or less, preferably 1 to 30% by mass, and more preferably 5 to 25% by mass. If the proportion of alcohol is too high, the raw material may not be properly dispersed in the aqueous dispersion and many may "dissolve". Therefore, the ratio of alcohol in the aqueous dispersion is preferably about the above.
  • T 1 is higher than 90 ° C. It tends to be low (about 30 to 90 ° C).
  • T 1 is lowered, delicate temperature adjustment becomes easy, and for example, crystal growth may be facilitated in a later crystallization step.
  • the effect of reducing impurities such as Ca ions (the more the aqueous dispersion is used, the easier it is for Ca ions in the raw material to move to the water-based dispersion) and the cost. It may be set appropriately from the balance of.
  • the amount of the aqueous dispersion with respect to 100 parts by mass of the raw material is usually 100 to 3000 parts by mass, preferably 200 to 1500 parts by mass.
  • the temperature T 1 varies depending on the specific structure of the compound (A) and the composition of the aqueous dispersion.
  • the heating temperature and time required in the melting step may be appropriately set accordingly.
  • the total amount of the compound (A) excluding the portion dissolved in the aqueous dispersion may be melted.
  • the temperature of the non-uniform liquid obtained in the melting step is lowered to crystallize the melt in the non-uniform liquid.
  • a compound in which Ca ions and the like are small and the particle size distribution is appropriately controlled for example, D m is 75 to 150 ⁇ m as in the first embodiment
  • the powder of (A) can be obtained. Further, by appropriately selecting the specific conditions for lowering the temperature, the powder of the compound (A) having a relatively small half-value width of the XRD spectrum can be obtained, probably because the size of the crystallite is controlled.
  • the crystallization step in the first process is different from the general crystallization step, that is, the crystallization of a substance dissolved in a uniform "solution".
  • a general crystallization step it is necessary to gradually lower the temperature of the solution as the crystals precipitate.
  • the temperature of the non-uniform liquid may be lowered to a certain temperature or less (less than the melting temperature), and the temperature does not necessarily have to be "gradually lowered". Most of compound (A) is not “melted” but simply "melted”, so as long as the temperature is kept below a certain temperature (less than the melting temperature), compound (A) Most of them crystallize (solidify).
  • the obtained crystal (final product) is different from the conventional product.
  • the aqueous dispersion medium contains alcohol
  • a certain amount of the compound (A) is "dissolved" in the dispersion medium, so that the temperature lowering operation may be performed at an appropriate rate.
  • the temperature may be lowered after the temperature is maintained at a constant temperature lower than the melting temperature.
  • the temperature T 2 in the crystallization step is preferably 1 to 10 ° C. lower than the temperature T 1 and more preferably 1 to 8 ° C. lower.
  • the system may be maintained at the above temperature T 2 (within a range of 1 to 10 ° C. lower than the temperature T 1 ), preferably for 30 minutes or longer, more preferably 60 minutes or longer. preferable.
  • the temperature T 2 for a sufficiently long time, Ca ions and the like were sufficiently reduced, and the particle size distribution was appropriately controlled (for example, D m is 75 to 150 ⁇ m as in the first embodiment). Easy to obtain crystals.
  • the time for maintaining the temperature T 2 in the crystallization step is preferably, for example, 300 minutes or less.
  • the crystallization step is preferably carried out while stirring the non-uniform liquid.
  • stirring is performed in the melting step, it is preferable to continue stirring as it is. By doing so, it is easy to sufficiently reduce the amount of impurities such as Ca ions.
  • the crystal growth is appropriately controlled and the particle size distribution is appropriately controlled (for example, D m is 75 to 150 ⁇ m as in the first embodiment). Easy to get.
  • the above stirring is preferably performed at a speed of 50 to 500 rpm, and more preferably at a speed of 150 to 300 rpm.
  • seed crystals may or may not be used.
  • the amount of the seed crystal added can be about 1/1000 to 1/100 of the compound (A) dispersed in the aqueous dispersion medium in terms of mass ratio.
  • the seed crystal is not particularly limited as long as it is a solid compound (A).
  • the system is usually cooled to room temperature (about 25 ° C.).
  • the cooling conditions are not particularly limited. It may or may not be naturally cooled.
  • a large amount of the compound (A) is not precipitated by cooling.
  • the aqueous dispersion medium dissolves a small amount of the compound (A)
  • some crystals are precipitated by cooling. From the viewpoint of precise adjustment of the amount of Ca ions and the like and the particle size distribution, it is preferable that the cooling is gently performed at about 0.1 to 0.3 [° C./min].
  • the obtained crystals can be recovered by, for example, vacuum filtration, washed with water, and dried under reduced pressure in an environment of about 20 to 50 ° C. to obtain the final powder.
  • the method for producing a powder of a compound represented by the general formula (A) includes, for example, a series of procedures such as the following steps 1 to 4. By such a procedure, the particle size distribution was appropriately controlled (for example, D 50 is 50 to 100 ⁇ m and D 50 / D ave is 1.1 to 1.5 as in the second embodiment). A powder of compound (A) can be obtained.
  • a substance containing a chemical structure represented by the general formula (A) is prepared.
  • a raw material can be obtained, for example, by the method described in Patent Document 2 described above.
  • Commercially available products may be used as raw materials.
  • Step 2 Dissolution in organic solvent (heating, etc.)
  • the raw material prepared in step 1 is put into an organic solvent. Then, the organic solvent is heated with stirring to dissolve the raw material in the organic solvent.
  • the organic solvent it is preferable to use a mixed solvent containing the poor solvent and the good solvent of the compound (A). As a result, in the subsequent (3) recrystallization, the crystals tend to grow slowly, and the particle size distribution is appropriately controlled (for example, as in the second embodiment, D 50 and D 50 / D ave). Easy to obtain (properly controlled) powder.
  • the poor solvent examples include alicyclic hydrocarbon solvents such as cyclohexane, methylcyclohexane and ethylcyclohexane, and n-pentane, n-hexane, isohexane, n-heptane, n-octane, isooctane, n-decane and the like.
  • aliphatic hydrocarbon solvent can be mentioned.
  • good solvents include ester solvents such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate, methyl lactate, ethyl lactate, and butyl lactate.
  • / Good solvent 95/5 to 80/20.
  • step 2 the organic solvent is heated to, for example, about 60 to 80 ° C. This heating and stirring completely dissolves the raw material in the organic solvent.
  • the amount of the raw material added to the organic solvent is adjusted so that the organic solvent is completely dissolved when heated to about 60 to 80 ° C., but precipitation occurs in step 3 (lowering temperature) described later.
  • This amount may be appropriately set based on the solubility of the raw material, the organic solvent used, the heating temperature, and the like.
  • the amount of the raw material used can be about 100 g per 1000 g of the organic solvent.
  • Step 3 Temperature lowering / addition of seed crystals / stirring
  • the organic solvent heated to about 60 to 80 ° C. and completely dissolved in the raw material was slowly brought to about 55 ° C. over about 30 minutes to 3 hours. To cool down.
  • the solid compound (A) is added to the organic solvent as a seed crystal.
  • the particle size distribution is finally appropriately controlled by using the seed crystal (for example, the second). It is easy to obtain the powder of the compound (A) in which D 50 and D 50 / D ave are controlled as in the embodiment.
  • the amount of the seed crystal added can be about 1/1000 to 1/100 of the raw material dissolved in the organic solvent in the step 2 in terms of mass ratio.
  • the seed crystal is not particularly limited as long as it is a solid compound (A).
  • a seed crystal obtained according to the method described in Examples of Patent Document 2 described above can be used.
  • a commercially available solid compound (A) can also be used as a seed crystal.
  • the organic solvent is stirred for about 30 minutes to 3 hours while maintaining the temperature of about 55 ° C. to precipitate the crystal.
  • Step 4 Cooling After the step 3, the organic solvent is slowly cooled to about 30 to 40 ° C. for about 1 to 5 hours while stirring. This causes the crystals to grow.
  • the obtained crystals are collected by vacuum filtration and dried under reduced pressure in an environment of about 20 to 50 ° C. By doing so, it is possible to obtain a powder having an appropriately controlled particle size distribution and the like.
  • a solution containing the compound represented by the general formula (A) can be produced by using the solvent and at least one of the powders of the first to fourth embodiments. By using this solution, various low molecular weight compounds, oligomers, polymers and the like can be produced.
  • the first to fourth embodiments may be added as it is to the solvent, and the mixture may be stirred or dissolved.
  • the first to fourth embodiments may be added. At least one of the powders of the embodiment may be finely divided to obtain a finely divided powder, and at least the finely divided powder may be added to a solvent and stirred or dissolved.
  • the industrial handleability of the powders of the first to fourth embodiments is good.
  • the mode diameter D m when the mode diameter D m is 75 to 150 ⁇ m, there are advantages such as “good filterability” and “the drying time when drying the wet powder can be shortened”. ..
  • the mode diameter D m is relatively large, 75 to 150 ⁇ m, there is a concern that it may take some time to dissolve depending on the type of solvent. Therefore, it may be preferable to produce the solution as described in (ii) above.
  • miniaturization is not particularly limited.
  • a typical miniaturization method is pulverization.
  • Industrially, pulverization can be performed using devices such as jet mills, roller mills, hammer mills, pin mills, rotary mills, vibration mills, planetary mills, and bead mills.
  • pulverization can be performed using devices such as jet mills, roller mills, hammer mills, pin mills, rotary mills, vibration mills, planetary mills, and bead mills.
  • at least one of the powders of the first to fourth embodiments is put into a solvent, and the undissolved powder is taken out (for example, by filtration) before being completely dissolved to be finely divided. Powder may be obtained.
  • At least one of the powders of the first to fourth embodiments is put into a solvent in an amount that does not dissolve the entire amount of the powder, and after the dissolution of the powder is saturated, it is not dissolved.
  • Fine powder may be obtained by taking out the powder of.
  • the solution containing the undissolved powder may be used as it is.
  • the degree of miniaturization is not particularly limited.
  • the degree of miniaturization may be determined by balancing the cost required for miniaturization with the merit of performing miniaturization (for example, the above-mentioned improvement in solubility).
  • the Dave may be 1/20 to 1/2, more preferably 1/15 to 1/4 before and after miniaturization (preferably pulverization).
  • D ave of the powder after fine (preferably crushed) is preferably 0.1 ⁇ 15 [mu] m, and more preferably may be such that the 0.5 ⁇ 10 [mu] m.
  • the solvent that can be used in producing the solution of compound (A) can be appropriately selected according to various purposes.
  • the solvent that can be used is not particularly limited as long as the compound (A) is dissolved.
  • amide-based solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformamide, hexamethylphosphate triamide, and N-methyl-2-pyrrolidone, methanol, ethanol, and 1-propanol.
  • Niterite solvents such as acetonitrile, propanenitrile, benzonitrile, aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, cumene, dichloromethane, chloroform, 1,2-dichloroethane, 1,1,2,2- Examples thereof include halogen-based solvents such as tetrachloroethane, and lactone-based solvents such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, and ⁇ -caprolactone.
  • the solvent may be used alone or in combination of two or more.
  • Example 1 to 5 and Comparative Examples 1 to 6 The following Examples 1 to 5 and Comparative Examples 1 to 6 are, in particular, Examples and Comparative Examples for explaining the first embodiment in detail.
  • Example 1 25.0 g (74.4 mmol) of BIS-AF powder manufactured by Central Glass Co., Ltd. was collected from a reagent bottle and placed in a glass container made of borosilicate glass having a volume of 500 mL equipped with a stirrer and a cooling condenser. Then, 225.0 g of pure water was added into the container. Then, the temperature inside the container was raised to 95 ° C. while stirring. While the temperature was being raised, the BIS-AF powder began to melt, and the inside of the container became suspended. The temperature was maintained at 95 ° C. and the mixture was stirred for 1 hour.
  • the internal temperature was slightly lowered from 95 ° C., and the mixture was stirred for 1 hour while maintaining the temperature of 92 to 94 ° C. Then, crystals were precipitated. Then, the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour. The room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 75 ° C. under reduced pressure (1 kPa or less) for 8 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 24.1 g, and the yield was 96%.
  • Example 2 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. Next, 202.5 g of pure water and 22.5 g of methanol were added into the container, and the temperature inside the container was raised to 66 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 1.5 hours.
  • the mixture was stirred for 1 hour while maintaining an internal temperature of 60 to 65 ° C. Then, crystals were precipitated. Then, the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour. The room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer. The BIS-AF powder obtained after drying was 22.9 g, and the yield was 92%.
  • Example 3 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. Next, 112.5 g of pure water and 12.5 g of methanol were added into the container, and the temperature inside the container was raised to 66 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 2 hours.
  • the mixture was stirred for 1 hour while maintaining an internal temperature of 59 to 65 ° C. Then, crystals were precipitated. Then, the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour. The room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer. The BIS-AF powder obtained after drying was 23.4 g, and the yield was 94%.
  • Example 4 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. Next, 100.0 g of pure water and 25.0 g of methanol were added into the container, and the temperature inside the container was raised to 40 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 2 hours.
  • the mixture was stirred for 1 hour while maintaining an internal temperature of 34 to 39 ° C. Then, crystals were precipitated. Then, the internal temperature was cooled to room temperature at a temperature lowering rate of 10 ° C./1 hour. The room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer. The BIS-AF powder obtained after drying was 23.0 g, and the yield was 92%.
  • Example 5 100.0 g (298 mmol) of BIS-AF powder manufactured by Central Glass Co., Ltd. was collected from a reagent bottle and placed in a glass container made of borosilicate glass having a volume of 2000 mL equipped with a stirrer and a cooling condenser. Then, 425.0 g of pure water and 75.0 g of methanol were added into the container. Then, the temperature inside the container was raised to 55 ° C. while stirring. While the temperature was being raised, the BIS-AF powder began to melt, and the inside of the container became suspended. The temperature was maintained at 55 ° C. and the mixture was stirred for 1 hour.
  • the internal temperature was slightly lowered from 55 ° C., and the mixture was stirred for 1 hour while maintaining the temperature of 49-50 ° C. Then, crystals were precipitated. Then, the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour. The room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 300 mL of pure water. The washed BIS-AF was dried at 75 ° C. under reduced pressure (1 kPa or less) for 8 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 95.1 g, and the yield was 95%.
  • Comparative Example 1 is an example in which an attempt is made to reduce Ca ions by simple washing with water.
  • BIS-AF powder 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 300 mL equipped with a stirrer. Next, 125.0 g of pure water was added, and the BIS-AF powder was washed while stirring at room temperature (about 20 ° C.) for 1 hour. After the washing was completed, the mixture was separated and collected by vacuum filtration using a suction filter equipped with a filter paper. Then, using a vacuum dryer, it was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours. The BIS-AF powder obtained after drying was 24.0 g, and the yield was 96%.
  • Comparative Example 2 is an example in which the reduction of Ca ions by reprecipitation, which is often attempted to reduce the amount of metal in the crystalline compound, is attempted.
  • Comparative Example 3 is an example in which an attempt was made to reduce Ca ions using activated carbon with reference to the description in Patent Document (CN104528717A).
  • BIS-AF was reprecipitated by gradually dropping this methanol solution into 200 g of pure water. After precipitation of BIS-AF, BIS-AF was recovered by vacuum filtration using a suction filter equipped with a filter paper. Then, using a vacuum dryer, it was dried at 80 ° C. under reduced pressure (1 kPa or less) for 8 hours. The BIS-AF powder obtained after drying was 21.9 g, and the yield was 88%.
  • Comparative Example 4 is an example in which the activated carbon is replaced with an ion exchange resin in Comparative Example 3.
  • BIS-AF powder 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 300 mL equipped with a stirrer. Next, 50.0 g of methanol and 2.0 g of an ion exchange resin (manufactured by Sumika Chemtex Co., Ltd., trade name, Duolite C255LFH) were added to the container, and the mixture was stirred at room temperature (about 20 ° C.) for 5 hours. After the stirring was completed, the ion exchange resin was removed by filtration using a suction filter equipped with a filter paper, and the methanol solution of BIS-AF was recovered.
  • an ion exchange resin manufactured by Sumika Chemtex Co., Ltd., trade name, Duolite C255LFH
  • BIS-AF was reprecipitated by gradually dropping this methanol solution into 200 g of pure water. After precipitation of BIS-AF, BIS-AF was recovered by vacuum filtration using a suction filter equipped with a filter paper. Then, using a vacuum dryer, it was dried at 80 ° C. under reduced pressure (1 kPa or less) for 7 hours. The BIS-AF powder obtained after drying was 22.2 g, and the yield was 89%.
  • Comparative Example 5 is an example in which activated carbon was replaced with activated clay in Comparative Example 3.
  • BIS-AF powder 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 1 and placed in a glass container made of borosilicate glass having a volume of 300 mL equipped with a stirrer. Next, 50.0 g of methanol and 2.0 g of activated clay (manufactured by Mizusawa Industrial Chemicals, Inc., trade name, galleon earth) were added to the container, and the mixture was stirred at room temperature (about 20 ° C.) for 5 hours. After the stirring was completed, the active clay was removed by filtration using a suction filter equipped with a filter paper, and the methanol solution of BIS-AF was recovered.
  • activated clay manufactured by Mizusawa Industrial Chemicals, Inc., trade name, galleon earth
  • Comparative Example 6 is an example referring to the matters described in Japanese Patent Application Laid-Open No. 2007-246819.
  • a mixed solvent of water and alcohol ethylene glycol
  • Comparative Example 6 was completely dissolved in the mixed solvent (became a uniform single layer), and Comparative Example 6 was essentially different from the present embodiment. different.
  • BIS-AF powder 150 g was put into a 2 L volume borosilicate glass container equipped with a stirrer and a cooling condenser from the same reagent bottle as in Example 1, and 300 g of ethylene glycol and 700 g of ion-exchanged water were poured into the container. .. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 85 ° C. The temperature was maintained as it was, and the mixture was stirred for 1 hour. After 1 hour, the stirring was stopped and the container was allowed to stand, and the inside of the container was observed. Then, a uniform solution was confirmed.
  • the flask was cooled at a temperature lowering rate of 10 ° C./hour until the internal temperature of the flask reached 25 ° C. Then, the crystals began to gradually precipitate (recrystallize) at the same time as the temperature lowering started.
  • the precipitated crystals were collected by filtration under reduced pressure (1 kPa or less) and dried under reduced pressure at 60 ° C.
  • the BIS-AF powder obtained after drying was 137.0 g, and the yield was 91%.
  • the concentration of Na ions was 0.2 ppm, and the concentration of Ca ions was 0.3 ppm.
  • ⁇ Measurement> (Diameter distribution) Using SALD-2200, a particle size distribution meter manufactured by Shimadzu Corporation, the particle size distribution of the obtained powder BIS-AF dispersed in an n-decane solvent was measured. At the time of measurement, BIS-AF and n-decane solvent were mixed in advance on a slide glass to prepare a paste-like BIS-AF. Then, paste-like BIS-AF is gradually added to n-decane, which is a dispersion solvent, and the amount of addition is adjusted so that the absorbance value is 0.1 L / (mol ⁇ cm) or less, and the particle size distribution is distributed. Was measured. By analyzing the obtained measurement results (particle size distribution), D m and the like were calculated.
  • Example / Comparative Example 0.4 g of each BIA-AF powder obtained in Example / Comparative Example was dissolved in 2.0 mL of t-butyl methyl ether to prepare a solution.
  • This solution and 2.0 mL of ultrapure water were placed in a separatory funnel, and the separatory funnel was vigorously shaken to extract a metal ion component on the ultrapure water (aqueous layer) side.
  • the separating funnel was allowed to stand, and the side of the separated aqueous layer was used as an analytical sample solution for analysis of metal ion components.
  • the metal ion content of this analytical sample solution was measured using an ion chromatography device (CS-2100) manufactured by Thermo Fisher Scientific.
  • a separation column (inner diameter 4 mm ⁇ 250 mm)) and a guard column (Ion Pac CG16 (inner diameter 4 mm ⁇ 100 mm)) were used.
  • a guard column (Ion Pac CG16 (inner diameter 4 mm ⁇ 100 mm)
  • the eluent 30 mM methanesulfonic acid was used, the eluent flow rate was 1.0 mL / min, and the temperature was 35 ° C.
  • Example 2 (Alcohol content)
  • 1.00 g of dried BIS-AF was dissolved in 1.00 g of ethyl acetate, and gas chromatography analysis was performed.
  • the methanol content was less than 100 ppm based on the peak area excluding ethyl acetate.
  • Comparative Example 6 1.00 g of BIS-AF after drying was dissolved in 1.00 g of ethyl acetate, and gas chromatography analysis was performed.
  • the ethylene glycol content was 500 ppm based on the peak area excluding ethyl acetate.
  • the filterability of the BIS-AF powders of Examples 1 to 5 was good. Further, from the evaluation results of the water content, it was found that the drying time when drying the BIS-AF powders of Examples 1 to 5 was short. That is, the BIS-AF powders of Examples 1 to 5 were excellent in industrial handleability.
  • the Ca ion content of the BIS-AF powders of Examples 1 to 5 was less than 1 ppm. From this, it was found that the BIS-AF powders of Examples 1 to 5 are preferably used in various technical fields (for example, manufacturing of electronic devices).
  • Examples 2-1 to 2-4 and Comparative Examples 2-1 to 2-3 The following Examples 2-1 to 2-4 and Comparative Examples 2-1 to 2-3 are, in particular, Examples and Comparative Examples for explaining the second embodiment in detail.
  • Example 2-1 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-hexane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • 1 g of BIS-AF manufactured by Central Glass Co., Ltd.
  • the target BIS-AF was precipitated by stirring for a time. After that, the mixture was cooled over 2 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration. The recovered crystals were dried under reduced pressure at 30 ° C. to obtain 24 g of BIS-AF in powder form.
  • Example 2-2 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-hexane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • the target BIS-AF was precipitated by stirring for a time. After that, the mixture was cooled over 4 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration. The recovered crystals were dried under reduced pressure at 30 ° C. to obtain 27 g of BIS-AF in powder form.
  • Example 2-3 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-heptane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • the desired BIS-AF was precipitated.
  • the mixture was cooled over 2 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration.
  • the recovered crystals were dried under reduced pressure at 30 ° C. to obtain 23 g of BIS-AF in powder form.
  • Comparative Example 2-1 is an example in which powder is produced by a method according to the example of Patent Document 2 (precipitation of BIF-AF by neutralization reaction).
  • 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) and 52 g of sodium hydroxide were placed in a 3 L flask made of borosilicate glass equipped with a stirring motor and a thermometer. Then, 1800 g of water was added while paying attention to heat generation, and the mixture was stirred to obtain a uniform solution (the salt of BIF-AF was dissolved). Then, the mixture was cooled to an internal temperature of 10 ° C.
  • Comparative Example 2-2 is an example in which the powder was produced by the method and conditions according to the examples of Patent Document 1 (the main component of the solvent is water).
  • 150 g of BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • 300 g of ethylene glycol and 700 g of ion-exchanged water were poured into the flask.
  • BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C.
  • BIS-AF was precipitated while cooling at a temperature lowering rate of 10 ° C./hour until the internal temperature of the flask reached 25 ° C.
  • the precipitated crystals were collected by vacuum filtration and dried under reduced pressure at 60 ° C. As a result, 135 g of powdery BIS-AF was obtained.
  • Comparative Example 2-3 is an example in which the powder was produced by the method and conditions according to the examples of Patent Document (CN104528717A) (precipitation of BIS-AF by reprecipitation).
  • 800 g of ion-exchanged water was poured into a 1 L flask made of borosilicate glass equipped with a stirring motor and a thermometer.
  • a solution prepared by dissolving 100 g of BIS-AF (manufactured by Central Glass Co., Ltd.) in 100 g of methanol was added dropwise thereto at an internal temperature of 20 to 23 ° C., and BIS-AF was reprecipitated while stirring the inside of the flask.
  • the precipitated crystals were collected by vacuum filtration and dried under reduced pressure at 60 ° C. As a result, 89 g of powdery BIS-AF was obtained.
  • Table 3 summarizes information on particle size.
  • the bulk density was measured using a JIS bulk specific gravity measuring instrument manufactured by Tsutsui Rikagaku Kikai.
  • the bulk specific gravity measuring instrument is provided with a funnel having a funnel diameter of 150 mm, a nozzle diameter of 12 mm, and a nozzle length of 22 mm, a shaking plate having a mesh opening of 0.5 mm on the funnel, and a cylindrical 30 mL receiver under the funnel nozzle.
  • 50 g of BIS-AF powder was taken on a shaking plate and slowly dropped into a receiver using a brush to allow natural filling. After scraping off the BIS-AF powder overflowing from the receiver, the looseness density was calculated by measuring the weight of the receiver. Further, when the BIS-AF powder was dropped, the hardness density was calculated from the weight obtained by compressing and filling the lower part of the receiver while lightly striking it.
  • Table 4 summarizes the results of various measurements / evaluations.
  • Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-3 The following Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-3 are, in particular, Examples and Comparative Examples for explaining the third embodiment in detail.
  • Example 3-1 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-hexane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • 1 g of BIS-AF manufactured by Central Glass Co., Ltd.
  • the target BIS-AF was precipitated by stirring for a time. After that, the mixture was cooled over 2 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration. The recovered crystals were dried under reduced pressure at 30 ° C. to obtain 24 g of BIS-AF in powder form.
  • Example 3-2 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-hexane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • the target BIS-AF was precipitated by stirring for a time. After that, the mixture was cooled over 4 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration. The recovered crystals were dried under reduced pressure at 30 ° C. to obtain 27 g of BIS-AF in powder form.
  • Example 3-3 First, 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) was placed in a 3 L flask made of borosilicate glass equipped with a stirring motor, a thermometer and a cooling condenser, and 1800 g of n-heptane and 200 g of ethyl acetate were poured into the flask. Then, using an oil bath, BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C. After the internal temperature of the flask reaches 65 ° C., the temperature is slowly lowered to 55 ° C.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • the desired BIS-AF was precipitated.
  • the mixture was cooled over 2 hours until the internal temperature reached 35 ° C., and the precipitated crystals were collected by vacuum filtration.
  • the recovered crystals were dried under reduced pressure at 30 ° C. to obtain 23 g of BIS-AF in powder form.
  • Comparative Example 3-1 is an example in which powder is produced by a method according to the example of Patent Document 2 (precipitation of BIF-AF by neutralization reaction).
  • 200 g of BIS-AF (manufactured by Central Glass Co., Ltd.) and 52 g of sodium hydroxide were placed in a 3 L flask made of borosilicate glass equipped with a stirring motor and a thermometer. Then, 1800 g of water was added while paying attention to heat generation, and the mixture was stirred to obtain a uniform solution (the salt of BIF-AF was dissolved). Then, the mixture was cooled to an internal temperature of 10 ° C.
  • Comparative Example 3-2 is an example in which the powder was produced by the method and conditions according to the examples of Patent Document 1 (the main component of the solvent is water).
  • 150 g of BIS-AF manufactured by Central Glass Co., Ltd.
  • BIS-AF manufactured by Central Glass Co., Ltd.
  • 300 g of ethylene glycol and 700 g of ion-exchanged water were poured into the flask.
  • BIS-AF was dissolved while heating and stirring until the internal temperature of the flask reached 65 ° C.
  • BIS-AF was precipitated while cooling at a temperature lowering rate of 10 ° C./hour until the internal temperature of the flask reached 25 ° C.
  • the precipitated crystals were collected by vacuum filtration and dried under reduced pressure at 60 ° C. As a result, 135 g of powdery BIS-AF was obtained.
  • Comparative Example 3-3 is an example in which the powder was produced by the method and conditions according to the examples of Patent Document (CN104528717A) (precipitation of BIS-AF by reprecipitation).
  • 800 g of ion-exchanged water was poured into a 1 L flask made of borosilicate glass equipped with a stirring motor and a thermometer.
  • a solution prepared by dissolving 100 g of BIS-AF (manufactured by Central Glass Co., Ltd.) in 100 g of methanol was added dropwise thereto at an internal temperature of 20 to 23 ° C., and BIS-AF was reprecipitated while stirring the inside of the flask.
  • the precipitated crystals were collected by vacuum filtration and dried under reduced pressure at 60 ° C. As a result, 89 g of powdery BIS-AF was obtained.
  • the bulk density was measured using a JIS bulk specific gravity measuring instrument manufactured by Tsutsui Rikagaku Kikai.
  • the bulk specific gravity measuring instrument is provided with a funnel having a funnel diameter of 150 mm, a nozzle diameter of 12 mm, and a nozzle length of 22 mm, a shaking plate having a mesh opening of 0.5 mm on the funnel, and a cylindrical 30 mL receiver under the funnel nozzle.
  • 50 g of BIS-AF powder was taken on a shaking plate and slowly dropped into a receiver using a brush to allow natural filling. After scraping off the BIS-AF powder overflowing from the receiver, the looseness density was calculated by measuring the weight of the receiver. Further, when the BIS-AF powder was dropped, the hardness density was calculated from the weight obtained by compressing and filling the lower part of the receiver while lightly striking it.
  • Example 4-1 to 4-5 and Comparative Examples 4-1 to 4-3 The following Examples 4-1 to 4-5 and Comparative Examples 4-1 to 4-3 are, in particular, Examples and Comparative Examples for explaining the fourth embodiment in detail.
  • Example 4-1 25.0 g (74.4 mmol) of BIS-AF powder manufactured by Tokyo Chemical Industry Co., Ltd. was collected from a reagent bottle and placed in a glass container made of borosilicate glass having a volume of 500 mL equipped with a stirrer and a cooling condenser. Next, 202.5 g of pure water and 22.5 g of methanol were added into the container, and the temperature inside the container was raised to 65 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 1.5 hours.
  • the solubility of the aqueous dispersion medium BIS-AF was well below 10 [g / 100 g].
  • the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour.
  • the room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 22.9 g, and the yield was 92%.
  • Example 4-2 BIS as in Example 4-1 except that the amount of BIS-AF powder was changed to 100.0 g (298 mmol), the amount of pure water was changed to 810.0 g, and methanol was changed to 90.0 g. -AF powder was obtained. The BIS-AF powder obtained after drying was 94.6 g, and the yield was 95%.
  • Example 4-3 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 4-1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. .. Then, 225.0 g of pure water was added into the container. Then, the temperature inside the container was raised to 95 ° C. while stirring. While the temperature was being raised, the BIS-AF powder began to melt, and the inside of the container became suspended. The temperature was maintained at 95 ° C. and the mixture was stirred for 1 hour.
  • the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour.
  • the room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 75 ° C. under reduced pressure (1 kPa or less) for 8 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 24.1 g, and the yield was 96%.
  • Example 4-4 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 4-1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. Next, 112.5 g of pure water and 12.5 g of methanol were added into the container, and the temperature inside the container was raised to 65 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 1.5 hours.
  • the internal temperature was cooled to room temperature at a temperature lowering rate of 15 ° C./1 hour.
  • the room temperature at this time was about 25 ° C.
  • the precipitated BIS-AF was separated and recovered by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 23.5 g, and the yield was 94%.
  • Example 4-5 25.0 g (74.4 mmol) of BIS-AF powder was collected from the same reagent bottle as in Example 4-1 and placed in a glass container made of borosilicate glass having a volume of 500 mL and equipped with a stirrer and a cooling condenser. Next, 100.0 g of pure water and 25.0 g of methanol were added into the container, and the temperature inside the container was raised to 45 ° C. with stirring. While the temperature was being raised, the BIS-AF powder began to melt and the inside of the container became suspended. The temperature was maintained as it was, and the mixture was stirred for 1.5 hours.
  • the precipitated BIS-AF was separated and collected by vacuum filtration using a suction filter equipped with a filter paper. After recovery, it was washed with 75 mL of pure water. The washed BIS-AF was dried at 80 ° C. under reduced pressure (1 kPa or less) for 6 hours using a vacuum dryer.
  • the BIS-AF powder obtained after drying was 24.1 g, and the yield was 96%.
  • BIS-AF manufactured by Tokyo Chemical Industry Co., Ltd.
  • BIS-AF manufactured by Tokyo Chemical Industry Co., Ltd.
  • X-ray diffraction (XRD) spectrum The X-ray diffraction (XRD) spectrum of the powder is based on the measurement method and measurement conditions described above.
  • Table 7 summarizes information on the X-ray diffraction spectrum.
  • the dispersion liquid in which the BIS-AF powder was dispersed in water was passed through a filter equipped with a filter paper and filtered to obtain a water-wet BIS-AF powder.
  • the obtained BIS-AF powder was placed in a vacuum dryer manufactured by Yamato Scientific Co., Ltd., dried at 0.5 KPa and 60 ° C., and the water content of the powder was measured.
  • the dissolution rates of the BIS-AF powders of Examples 4-1, 4-4 and 4-5 were good. Further, from the evaluation results of the water content, it was found that the drying time when drying the BIS-AF powders of Examples 4-1, 4-4 and 4-5 was short. That is, the BIS-AF powder of Example 4-1 and the like was excellent in industrial handleability.
  • Example 4-1 the "moisture absorption test” was performed as follows. (Hygroscopic test) 10 g of BIS-AF powder was weighed on a charley, and the water content of the BIS-AF powder was measured with a capacitive Karl Fischer (MKV-710B, manufactured by Kyoto Denshi Kogyo Co., Ltd.). In addition, 10 g of BIS-AF powder is weighed in a charley and allowed to stand in a constant temperature and humidity chamber at a temperature of 30 ° C. and a humidity of 98%. MKV-710B, manufactured by Kyoto Electronics Industry Co., Ltd.).
  • the water content of the BIS-AF powder of Example 4-1 did not change even after 24 hours, and it was found that it was difficult to absorb moisture. That is, the BIS-AF powder of Example 4-1 was excellent in industrial handleability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une poudre d'un composé représenté par la formule générale (A). Par exemple, le diamètre modal Dm de cette poudre, mesuré à l'aide de la méthode de diffusion/diffraction laser, est de 75 à 150 µm et la teneur en ions Ca est inférieure à 1 ppm. Dans la formule générale (A), R1 à R8 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C4, un atome d'halogène ou un groupe amino. Cette poudre peut être obtenue par un procédé comprenant, par exemple, une étape de fusion (i) dans laquelle une substance de départ est fondue en présence d'un fluide vecteur aqueux et un fluide hétérogène est obtenu, par l'introduction dans un récipient et le chauffage de la substance de départ, qui comprend un composé représenté par la formule générale (A), et d'un fluide vecteur aqueux (un mauvais solvant du composé représenté par la formule générale (A)) ; et une étape de cristallisation (ii) dans laquelle la masse fondue est cristallisée par abaissement de la température du fluide hétérogène.
PCT/JP2020/035950 2019-09-30 2020-09-24 Poudre, procédé de production de poudre et procédé de production de solution WO2021065653A1 (fr)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0267239A (ja) * 1988-08-31 1990-03-07 Central Glass Co Ltd ２，２−ビス（４−ヒドロキシフェニル）ヘキサフルオロプロパンの精製法
JPH0454144A (ja) * 1990-06-22 1992-02-21 Central Glass Co Ltd ヘキサフルオロプロピリデン基含有芳香族化合物の精製法
JPH06145090A (ja) * 1992-11-02 1994-05-24 Honsyu Kagaku Kogyo Kk 光学特性に優れたビスフェノールａｆ及びその製造方法
JPH06211752A (ja) * 1993-01-18 1994-08-02 Central Glass Co Ltd ２，２−ビス（３−ニトロ−４−ヒドロキシフェニル）ヘキサフルオロプロパンの製造方法
JP2004131386A (ja) * 2002-10-08 2004-04-30 Nippon Kayaku Co Ltd ジアミノフェノール類の製造方法
CN1919812A (zh) * 2006-09-12 2007-02-28 上海三爱富新材料股份有限公司 六氟亚甲基芳香族化合物的精制方法
JP2007246819A (ja) * 2006-03-17 2007-09-27 Japan Epoxy Resin Kk 発光素子封止材用エポキシ樹脂組成物
JP2012184173A (ja) * 2011-03-03 2012-09-27 Toray Fine Chemicals Co Ltd ビス（アミノヒドロキシフェニル）類の精製方法
CN104529717A (zh) * 2014-12-24 2015-04-22 常熟市新华化工有限公司 一种制备双苯酚六氟丙烷的方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0267239A (ja) * 1988-08-31 1990-03-07 Central Glass Co Ltd ２，２−ビス（４−ヒドロキシフェニル）ヘキサフルオロプロパンの精製法
JPH0454144A (ja) * 1990-06-22 1992-02-21 Central Glass Co Ltd ヘキサフルオロプロピリデン基含有芳香族化合物の精製法
JPH06145090A (ja) * 1992-11-02 1994-05-24 Honsyu Kagaku Kogyo Kk 光学特性に優れたビスフェノールａｆ及びその製造方法
JPH06211752A (ja) * 1993-01-18 1994-08-02 Central Glass Co Ltd ２，２−ビス（３−ニトロ−４−ヒドロキシフェニル）ヘキサフルオロプロパンの製造方法
JP2004131386A (ja) * 2002-10-08 2004-04-30 Nippon Kayaku Co Ltd ジアミノフェノール類の製造方法
JP2007246819A (ja) * 2006-03-17 2007-09-27 Japan Epoxy Resin Kk 発光素子封止材用エポキシ樹脂組成物
CN1919812A (zh) * 2006-09-12 2007-02-28 上海三爱富新材料股份有限公司 六氟亚甲基芳香族化合物的精制方法
JP2012184173A (ja) * 2011-03-03 2012-09-27 Toray Fine Chemicals Co Ltd ビス（アミノヒドロキシフェニル）類の精製方法
CN104529717A (zh) * 2014-12-24 2015-04-22 常熟市新华化工有限公司 一种制备双苯酚六氟丙烷的方法

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