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WO2016002607A1 - Nouveaux bis(hydroxyalcoxyphényl)diphénylméthanes - Google Patents

Nouveaux bis(hydroxyalcoxyphényl)diphénylméthanes Download PDF

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Publication number
WO2016002607A1
WO2016002607A1 PCT/JP2015/068286 JP2015068286W WO2016002607A1 WO 2016002607 A1 WO2016002607 A1 WO 2016002607A1 JP 2015068286 W JP2015068286 W JP 2015068286W WO 2016002607 A1 WO2016002607 A1 WO 2016002607A1
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Prior art keywords
group
bis
general formula
diphenylmethane
reaction
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PCT/JP2015/068286
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English (en)
Japanese (ja)
Inventor
祐樹 橋本
緒旺 路
耕司 村垣
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本州化学工業株式会社
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Priority to KR1020167032858A priority Critical patent/KR102357570B1/ko
Priority to CN201580029942.5A priority patent/CN106458817B/zh
Priority to JP2016531304A priority patent/JP6826885B2/ja
Publication of WO2016002607A1 publication Critical patent/WO2016002607A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/46—Use of additives, e.g. for stabilisation

Definitions

  • the present invention relates to novel bis (hydroxyalkoxyphenyl) diphenylmethanes, and more particularly to a dihydroxy compound having a diphenylmethane skeleton.
  • aromatic dihydroxy compounds are useful as raw materials for various chemical products such as aromatic polyester resins, polycarbonate resin raw materials, and high refractive resin raw materials for acrylic derivatives.
  • polynuclear aromatic polyvalent hydroxy compounds such as aromatic dihydroxy compounds have been used as highly functional resin raw materials such as heat resistant resins.
  • aromatic dihydroxyalkoxy compounds having a diphenylmethane skeleton such as 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1,1-diphenylmethane are used as polyester resins. It is used as a raw material for monomers and acrylic derivatives of high refractive resin raw materials (Patent Document 1, Patent Document 2, Patent Document 3).
  • 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1,1-diphenylmethane has a high melting point and low solubility in a solvent, and is poor in operability and processability. If it is used, it will take a long time to dissolve or melt, or more solvents and higher temperatures may be required.
  • compounds such as 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1-phenylethane have a low melting point and high solvent solubility, the resulting resin has a refractive index and a glass transition temperature. It was low (patent document 4). Accordingly, there is a demand for an aromatic dihydroxyalkoxy compound that has high solubility, a low melting point and good operability, and that can improve properties such as optical properties and heat resistance.
  • an object of the present invention is to provide a new aromatic dihydroxyalkoxy compound that has high solubility, low melting point, good operability, and can improve optical properties and heat resistance.
  • the present inventors have intensively studied the above-mentioned problems of aromatic dihydroxyalkoxy compounds having a tetraphenyl skeleton such as 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1,1-diphenylmethane.
  • a polynuclear aromatic dihydroxyalkoxy compound in which a phenyl group having a hydroxyalkoxy group in 1,1-bis [4- (2-hydroxyalkoxy) phenyl] -1,1-diphenylmethane is further substituted with a phenyl group has a low melting point.
  • the present invention has been completed by finding that it has excellent solubility in organic solvents and has the same or superior refractive index and glass transition temperature.
  • R represents an alkylene group having 2 to 6 carbon atoms
  • R 1 is a phenyl group
  • R 2 is each independently an alkyl group having 1 to 6 carbon atoms, or 1 to 6 carbon atoms
  • a represents an integer of 1 to 3
  • b represents 0 or an integer of 1 to 3, provided that when b is 2 or more, R 2 may be the same or different;
  • 1 ⁇ a + b ⁇ 4. It is bis (hydroxyalkoxyphenyl) diphenylmethane represented by these.
  • the bis (hydroxyalkoxyphenyl) diphenylmethanes of the present invention have a diphenylmethane skeleton, and furthermore, an aromatic dinuclear aromatic hydrocarbon having a structure in which a phenyl group substituted by a hydroxyalkoxy group is substituted by a phenyl group. It is alcohol.
  • the aromatic dialcohol of the present invention has a lower melting point and better solubility than conventional bis ⁇ 4- (2-hydroxyethoxy) phenyl ⁇ diphenylmethane, for example. Therefore, operability in reaction and purification can be improved. For example, when industrially used in large quantities, the melting or dissolution time can be shortened.
  • the bis (hydroxyalkoxyphenyl) diphenylmethanes of the present invention are represented by the above general formula (1).
  • the substitution position of R 1 which is a phenyl group substituted by a phenyl group substituted by a hydroxyalkoxy group is preferably an ortho position of the hydroxyalkoxy group.
  • the phenyl group substituted with a phenyl group substituted with a hydroxyalkoxy group may be substituted with an alkyl group or an alkoxyl group having about 1 to 3 carbon atoms within a range not inhibiting the effect of the present invention. Although it is good, it is preferable that it is not substituted from the viewpoint of heat resistance and refractive index.
  • A represents an integer of 1 to 3, preferably 1 or 2, and more preferably 1.
  • each R 2 independently represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.
  • the alkyl group having 1 to 6 carbon atoms is preferably a linear or branched alkyl group having 1 to 4 carbon atoms or a cyclic alkyl group having 5 to 6 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the alkoxy group having 1 to 6 carbon atoms is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms or a cyclic alkoxy group having 5 to 6 carbon atoms.
  • Examples include ethoxy group, propoxy group, t-butoxy group, cyclohexyloxy and the like.
  • Specific examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.
  • R 2 an alkyl group is preferable, and a methyl group is more preferable.
  • substitution position of R 2 is preferably the ortho position of the hydroxyalkoxy group.
  • B represents 0 or an integer of 1 to 3, preferably 0, 1 or 2, and more preferably 0 or 1 from the viewpoint of heat resistance and refractive index.
  • R 2 may be the same or different and is in the range of 1 ⁇ a + b ⁇ 4.
  • R represents an alkylene group having 2 to 6 carbon atoms.
  • the alkylene group is preferably a linear or branched alkylene group, preferably an alkylene group having 2 to 4 carbon atoms, and particularly preferably an alkylene group having 2 or 3 carbon atoms. Therefore, specific examples of R include 1,2-ethylenediyl group, 1,2-propanediyl group, 1,3-propanediyl group, pentamethylene group, hexamethylene group and the like.
  • the bonding position of the hydroxy group bonded to the alkylene group R is the carbon atom constituting the alkylene group R directly bonded to the ether group (position 1). It is called a carbon atom.) That is, the alkylene group R is bonded to the 2-6 position carbon atoms. When R has 3 or more carbon atoms, it is preferably bonded to the 2- or 3-position of the alkylene group R, more preferably the 2-position. Therefore, specific examples of preferred hydroxyalkoxy groups include 2-hydroxyethoxy group, 2-hydroxypropoxy group, 2-hydroxy-1-methylethoxy group, 3-hydroxypropoxy group and the like.
  • preferred bis (hydroxyalkoxyphenyl) diphenylmethanes are bis (hydroxyethoxyphenyl) diphenylmethanes, which are represented by the following general formula: It is represented by (2).
  • General formula (2) (Wherein R 1 , R 2 , a and b are the same as those in formula (1), and R 3 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, provided that each The total number of carbon atoms of R 3 substituted on the hydroxyethoxy group is 4 or less.)
  • examples of the alkyl group represented by R 3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isobutyl group.
  • R 3 is preferably a hydrogen atom or a methyl group.
  • R 3 substituted for each hydroxyethoxy group when two R 3 are bonded to the same carbon atom, it is preferable that at least one of the two R 3 is a hydrogen atom. More preferably, R 3 are all hydrogen atoms.
  • preferred bis (hydroxyalkoxyphenyl) diphenylmethanes include, for example, 1,1-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] -1,1-diphenylmethane, 1,1-bis [4- (2-hydroxypropoxy) -3-phenylphenyl] -1,1-diphenylmethane, 1,1-bis [4- (2-hydroxy-1-methylethoxy) -3-phenylphenyl ] -1,1-diphenylmethane, 1,1-bis [4- (3-hydroxypropoxy) -3-phenylphenyl] -1,1-diphenylmethane, 1,1-bis [4- (2-hydroxyethoxy)- 3,5-diphenylphenyl] -1,1-diphenylmethane, 1,1-bis [4- (2-hydroxyethoxy) -3-methyl-5-phenylphenyl] -1,1-diphenylmethane,
  • the production method of the bis (hydroxyalkoxyphenyl) diphenylmethanes represented by the general formula (1) of the present invention preferably bis (hydroxyethoxyphenyl) diphenylmethanes is not particularly limited, and is produced using a known method. Can do.
  • Examples include a method of producing by reacting in a solvent.
  • the method using alkylene carbonates or alkylene oxides is mainly a bis (hydroxyethoxyphenyl) diphenylmethane of the above general formula (2), which is a preferred embodiment of the present invention, mainly from the viewpoint of economy. It is preferable as a production method.
  • reaction formula (1) 1,1-bis (4-hydroxy-3-phenylphenyl) -1,1-diphenylmethane and ethylene carbonate is represented by the following reaction formula (1).
  • the raw material bisphenol represented by the general formula (3) is preferably, for example, 1,1-bis (4-hydroxy-3-phenylphenyl) -1,1-diphenylmethane, 1,1 -Bis (5-methyl-4-hydroxy-3-phenylphenyl) -1,1-diphenylmethane, 1,1-bis (2-methyl-4-hydroxy-5-phenylphenyl) -1,1-diphenylmethane, , 1-bis (4-hydroxy-3,5-diphenylphenyl) -1,1-diphenylmethane, 1,1-bis (4-hydroxy-2-phenylphenyl) -1,1-diphenylmethane, and the like.
  • examples of the alkylene carbonate represented by the general formula (4) include ethylene carbonate, propylene carbonate, 1,2-butylene carbonate and the like.
  • the amount of alkylene carbonate used is usually in the range of about 2 to 10 moles, preferably in the range of about 3 to 5 moles per mole of bisphenols.
  • the reaction is usually performed in the presence of a base catalyst.
  • the base catalyst include alkali catalysts such as sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and quaternary ammonium halides such as tetrabutylammonium bromide, tetraethylammonium chloride and tetramethylammonium chloride.
  • the amount of the catalyst is usually in the range of 0.005 to 0.5 mol, preferably in the range of 0.01 to 0.3, with respect to 1 mol of the bisphenol.
  • the reaction temperature is usually in the range of 100 to 150 ° C, preferably in the range of 120 to 130 ° C.
  • Solvents include aromatic hydrocarbon solvents such as toluene and xylene, ketone solvents such as acetone and methyl isobutyl ketone, ether solvents such as tetrahydrofuran, dioxane and 1,2-diethoxyethane, 1-butanol and 2-butanol. Examples thereof include aliphatic alcohol solvents such as ethylene glycol, and aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.
  • the amount of the solvent is, for example, preferably 50 to 300 parts by weight, more preferably 100 to 200 parts by weight with respect to 100 parts by weight of bisphenols.
  • the reaction may be performed, for example, by charging reaction raw materials, catalyst, solvent, etc. into a reaction vessel at once and raising the temperature to the reaction temperature, or raising the temperature of the mixture of bisphenols, solvent, and catalyst to a predetermined temperature. Further, alkylene carbonates may be dropped there. After completion of the reaction, the target product can be taken out from the reaction mixture as a crude product or a high-purity product by a known purification method. For example, after completion of the reaction, water is added to the reaction completion mixture to decompose excess alkylene carbonate. When an alkali catalyst is used, it may be neutralized by adding an acid.
  • a solvent that separates from water is added, and then the oil layer is washed with water to remove the catalyst or neutralized salt. Then, after cooling an oil layer or concentrating an oil layer, it melt
  • the raw material bisphenol represented by the general formula (3) can be produced by a known method.
  • it can be obtained by a method in which the phenylphenol represented by the general formula (7) and the dichlorodiphenylmethane represented by the general formula (8) corresponding to the bisphenol are reacted under heating.
  • the above reaction is represented by a reaction formula.
  • the reaction for obtaining 1,1-bis (4-hydroxy-3-phenylphenyl) -1,1-diphenylmethane by the reaction of 2-phenylphenols with dichlorodiphenylmethane is the following reaction. It is represented by Formula (2).
  • the molar ratio of dichlorodiphenylmethanes and phenylphenols is usually in the range of 2 to 10 moles, preferably 2.5 to 5 moles of phenyl-substituted phenols per mole of dichlorodiphenylmethanes. is there.
  • the catalyst may not be used.
  • the solvent is not particularly required if the raw materials can be mixed in a liquid state, but it is preferable to use the solvent if the raw materials cannot be mixed for reasons such as a solid at the reaction temperature.
  • the solvent used is not particularly limited as long as it does not inhibit the reaction.
  • an aromatic hydrocarbon solvent such as toluene and xylene
  • a saturated hydrocarbon solvent such as n-heptane and cyclohexane
  • an ether type such as dioxane and tetrahydrofuran.
  • a solvent etc. are mentioned.
  • the reaction raw materials may be charged and reacted all at once, or after phenylphenols are charged, dichlorodiphenylmethanes are dropped and reacted at a low temperature, and then the temperature is raised to further react. You may let them.
  • the desired product can be obtained as a crude product or a refined product from the reaction mixture by a known purification method.
  • the reaction mixture was cooled to 30 ° C., neutralized by adding a 16% aqueous sodium hydroxide solution to the reaction mixture, and the precipitated crystals were separated by filtration.
  • the obtained crystals were dried at 60 ° C. under reduced pressure to obtain 97.5 g of yellow powdery crystals having a purity of 74.7% (according to high performance liquid chromatography analysis).
  • Distilled water was added to the solution and stirred, and a water washing operation for separating and removing the aqueous layer was performed 4 times.
  • the water-washed oil layer was concentrated to 78.9 g, and then cooled and crystallized. After cooling to room temperature, the precipitated crystals are separated by filtration, dried, and 1,1-bis (3-phenyl-4-hydroxyphenyl) -1,1 having a purity of 99.0% as determined by high performance liquid chromatography analysis. -12.9 g of diphenylmethane was obtained. Melting point: 290.8 ° C.
  • Example 1 A 200 ml four-necked flask equipped with a stirrer was purged with nitrogen, and 14.5 g of 1,1-bis (4-hydroxy-3-phenylphenyl) diphenylmethane having a purity of 96.7%, 7.6 g of ethylene carbonate, 0.3 g of potassium hydroxide, 0.3 g of tetrabutylammonium bromide and 72.5 g of n-butanol were charged, the temperature was raised to 115 ° C., and the mixture was stirred at a temperature of 115 ° C. to 120 ° C. for 44 hours.
  • 1,1-1,1- 1 as a white powder having a purity of 97.8% (according to high performance liquid chromatography analysis).
  • 13.8 g of bis [4- (2-hydroxyethoxy) -3-phenylphenyl] -1,1-diphenylmethane was obtained.
  • the yield based on the raw material 1,1-bis (4-hydroxy-3-phenylphenyl) -1,1-diphenylmethane was 81.2 mol%.
  • ⁇ Glass transition temperature measurement method> In a differential scanning calorimeter, each compound was melted, cooled, and heated again to measure the glass transition point. At this time, the measurement start temperature was 30 ° C., and the temperature elevation rate was 10 ° C./min.
  • a saturated solution was prepared by adding 3 g of a solvent to a test tube and adding a compound to be measured at a measurement temperature. The concentration of the supernatant of this saturated solution was measured with a calibration curve by liquid chromatography.
  • Example 1 Measurement of Compound Physical Properties
  • the glass transition temperature, melting point and refractive index of 1,1-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] -1,1-diphenylmethane of Example 1 were measured and summarized in Table 3. Furthermore, the compound concentration in the saturated solution was measured and summarized in Table 4.
  • the glass transition temperature, melting point, and refractive index of 1,1-bis [4- (2-hydroxyethoxy) phenyl] -1,1-diphenylmethane (BisPDP-2EO) having a purity of 98.9% were measured and summarized in Table 3. It was. Furthermore, the compound concentration in the saturated solution was measured and summarized in Table 4.
  • the compound of the present invention in which the phenyl group is further bonded to the phenyl group to which the hydroxyethoxy group is bonded has a lower melting point than BisPDP-2EO in which the phenyl group is not further bonded, And it can be understood that the solubility in a solvent is high.
  • an alkyl group, an alkoxy group or a halogen atom is further bonded to the phenyl group to which the hydroxyethoxy group is bonded together with the phenyl group, or the number of carbon atoms is 3 instead of the ethylene group to which the hydroxy group of the hydroxyethoxy group is bonded.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention a pour but de fournir un nouveau composé dihydroxyalcoxy aromatique qui est extrêmement soluble, qui est extrêmement transformable à un bas point de fusion et qui peut améliorer des propriétés optiques et d'autres propriétés telles que la résistance à la chaleur. Pour atteindre ce but, la présente invention porte sur des bis(hydroxyalcoxyphényl)diphénylméthanes représentés par la formule générale (1). (Dans la formule, R représente un groupe alkylène en C2-6 ; R1 représente un groupe phényle ; les R2 représentent chacun indépendamment un groupe alkyle en C1-6, un groupe alcoxy en C1-6 ou un atome d'halogène ; a représente un nombre entier de 1 à 3 ; b représente 0 ou un nombre entier de 1 à 3, si b est supérieur ou égal à 2, les R2 pouvant être identiques ou différents et 1 ≤ a + b ≤ 4.)
PCT/JP2015/068286 2014-06-30 2015-06-25 Nouveaux bis(hydroxyalcoxyphényl)diphénylméthanes WO2016002607A1 (fr)

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KR1020167032858A KR102357570B1 (ko) 2014-06-30 2015-06-25 신규한 비스(히드록시알콕시페닐)디페닐메탄류
CN201580029942.5A CN106458817B (zh) 2014-06-30 2015-06-25 新型的双(羟基烷氧基苯基)二苯甲烷类
JP2016531304A JP6826885B2 (ja) 2014-06-30 2015-06-25 新規なビス（ヒドロキシアルコキシフェニル）ジフェニルメタン類

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Cited By (2)

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WO2017038979A1 (fr) * 2015-09-03 2017-03-09 三菱瓦斯化学株式会社 Composé et son procédé de production, composition, composition pour former un composant optique, composition pour former un film de lithographie, composition de réserve, procédé de formation d'un motif de réserve, composition sensible aux rayonnements, procédé de production d'un film amorphe, matériau pour former un film de sous-couche lithographique, composition pour former un film de sous-couche lithographique, procédé de production d'un film de sous-couche lithographique, procédé de formation d'un motif de circuit et procédé de purification
WO2018016615A1 (fr) * 2016-07-21 2018-01-25 三菱瓦斯化学株式会社 Composé, résine, composition, procédé de formation de motif de réserve et procédé de formation de circuit

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Publication number Priority date Publication date Assignee Title
WO2017038979A1 (fr) * 2015-09-03 2017-03-09 三菱瓦斯化学株式会社 Composé et son procédé de production, composition, composition pour former un composant optique, composition pour former un film de lithographie, composition de réserve, procédé de formation d'un motif de réserve, composition sensible aux rayonnements, procédé de production d'un film amorphe, matériau pour former un film de sous-couche lithographique, composition pour former un film de sous-couche lithographique, procédé de production d'un film de sous-couche lithographique, procédé de formation d'un motif de circuit et procédé de purification
US20180246407A1 (en) * 2015-09-03 2018-08-30 Mitsubishi Gas Chemical Company, Inc. Compound, composition, and method for producing same, underlayer film forming material for lithography, composition for underlayer film formation for lithography, and purification method
EP3345889A4 (fr) * 2015-09-03 2019-04-17 Mitsubishi Gas Chemical Company, Inc. Composé et son procédé de production, composition, composition pour former un composant optique, composition pour former un film de lithographie, composition de réserve, procédé de formation d'un motif de réserve, composition sensible aux rayonnements, procédé de production d'un film amorphe, matériau pour former un film de sous-couche lithographique, composition pour former un film de sous-couche lithographique, procédé de production d'un film de sous-couche lithographique, procédé de formation d'un motif de circuit et procédé de purification
US11067889B2 (en) 2015-09-03 2021-07-20 Mitsubishi Gas Chemical Company, Inc. Compound, composition, and method for producing same, underlayer film forming material for lithography, composition for underlayer film formation for lithography, and purification method
WO2018016615A1 (fr) * 2016-07-21 2018-01-25 三菱瓦斯化学株式会社 Composé, résine, composition, procédé de formation de motif de réserve et procédé de formation de circuit
CN109476576A (zh) * 2016-07-21 2019-03-15 三菱瓦斯化学株式会社 化合物、树脂、组合物以及抗蚀图案形成方法及电路图案形成方法
JPWO2018016615A1 (ja) * 2016-07-21 2019-05-09 三菱瓦斯化学株式会社 化合物、樹脂、組成物並びにレジストパターン形成方法及び回路パターン形成方法
JP7069529B2 (ja) 2016-07-21 2022-05-18 三菱瓦斯化学株式会社 化合物、樹脂、組成物並びにレジストパターン形成方法及び回路パターン形成方法

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TW201609622A (zh) 2016-03-16
TWI655183B (zh) 2019-04-01
CN106458817A (zh) 2017-02-22
KR20170026341A (ko) 2017-03-08
JP6826885B2 (ja) 2021-02-10
JPWO2016002607A1 (ja) 2017-04-27
KR102357570B1 (ko) 2022-01-28

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