WO2011016583A1 - Procédé de fabrication d'un polyéther aromatique - Google Patents

Procédé de fabrication d'un polyéther aromatique Download PDF

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Publication number
WO2011016583A1
WO2011016583A1 PCT/JP2010/063593 JP2010063593W WO2011016583A1 WO 2011016583 A1 WO2011016583 A1 WO 2011016583A1 JP 2010063593 W JP2010063593 W JP 2010063593W WO 2011016583 A1 WO2011016583 A1 WO 2011016583A1
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WIPO (PCT)
Prior art keywords
compound
mol
aromatic polyether
less
phenol compound
Prior art date
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PCT/JP2010/063593
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English (en)
Japanese (ja)
Inventor
大塚貴之
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住友化学株式会社
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Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Publication of WO2011016583A1 publication Critical patent/WO2011016583A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used

Definitions

  • the present invention relates to a method for producing an aromatic polyether. Specifically, the present invention relates to a method for reliably producing an aromatic polyether having a predetermined molecular weight.
  • Aromatic polyether is useful as a polymer compound excellent in heat resistance, impact resistance, transparency and the like.
  • Such an aromatic polyether is produced by polycondensation reaction of a dihydric phenol compound and a dihalogenodiphenyl compound in the presence of a base and a reaction solvent (for example, Japanese Patent Application Laid-Open No. 2004-315664 (Patent Document 1)). JP, 2008-248013, A (patent documents 2)). Since the molecular weight of the aromatic polyether affects the physical properties, it is required to produce an aromatic polyether having a predetermined molecular weight.
  • an aromatic polyether when produced by polycondensation reaction so as to obtain a target molecular weight, an aromatic polyether having a molecular weight lower than the target molecular weight may be obtained.
  • a method for reliably producing aromatic polyethers is desired.
  • An object of the present invention is to provide a method for more reliably producing an aromatic polyether having a target molecular weight.
  • the present invention relates to a method for producing an aromatic polyether by subjecting a dihydric phenol compound and a dihalogenodiphenyl compound to a polycondensation reaction in the presence of a reaction solvent and a base, and the monohalogenodiphenyl compound contained in the raw material
  • a method for producing an aromatic polyether in which a polycondensation reaction is carried out under the condition that the amount of the dihalogenodiphenyl compound is 0.25 mol% or less and the amount of the monohydric phenol compound is 0.25 mol% or less of the dihydric phenol compound I will provide a.
  • an aromatic polyether having a target molecular weight can be more reliably produced.
  • the aromatic polyether is produced by polycondensing a dihydric phenol compound and a dihalogenodiphenyl compound in the presence of a reaction solvent and a base.
  • the dihydric phenol compound is a phenol compound having two phenolic hydroxyl groups.
  • Lower alkoxy groups such as Atom, a bromine atom, and those which are substituted with a halogen atom such as fluorine atom.
  • a mixture of two or more thereof may be used.
  • hydroquinone, 4,4′-biphenol, 2,2-bis (4-hydroxyphenyl) propane, 4,4′-dihydroxydiphenyl ether, or 4,4′-dihydroxydiphenyl sulfone is preferably used.
  • the dihalogenodiphenyl compound is a compound having two halogenophenyl groups, and a dihalogenodiphenyl compound having a sulfone group, for example, a dihalogenodiphenylsulfone such as 4,4′-dichlorodiphenylsulfone or 4,4′-difluorodiphenylsulfone.
  • 1,4-bis (4-chlorophenylsulfonyl) benzene bis (halogenophenylsulfonyl) benzenes such as 1,4-bis (4-fluorophenylsulfonyl) benzene, and 1,4-bis (4-chlorophenylsulfonyl) ) Biphenyl, 1,4-bis (4-fluorophenylsulfonyl) biphenyl and other bis (halogenophenylsulfonyl) biphenyls, and ketone compounds having two halogenophenyl groups such as 4,4′-dichlorodiphenyl ketone, 4'-di Dihalogenodiphenyl ketones such as fluorodiphenyl ketone, bis (halogenophenylcarbonyl) benzenes such as 1,4-bis (4-chlorophenylcarbonyl) benzene, 1,4-bis (4-fluoroph
  • dihalogenodiphenyl sulfones such as 4,4′-dichlorodiphenyl sulfone and 4,4′-difluorodiphenyl sulfone are preferably used.
  • reaction solvent examples include sulfoxide solvents such as dimethyl sulfoxide and hexamethylene sulfoxide, amide solvents such as N, N-dimethylformamide and N, N-dimethylacetamide, N-methyl-2-pyrrolidone, and N-vinyl-2- Pyrrolidone solvents such as pyrrolidone, piperidone solvents such as N-methyl-2-piperidone, 2-imidazolinone solvents such as 1,3-dimethyl-2-imidazolidinone, diphenyl compounds such as diphenyl ether and diphenyl sulfone, ⁇ -Lactone solvents such as butyrolactone, sulfolane solvents such as sulfolane, and mixtures of two or more of these.
  • sulfoxide solvents such as dimethyl sulfoxide and hexamethylene sulfoxide
  • amide solvents such as N, N-dimethylformamide and N,
  • diphenyl compounds such as diphenylsulfone are preferably used.
  • the base is dehydrohalogenated from the phenolic hydroxyl group of the dihydric phenol compound and the halogen atom of the dihalogenodiphenyl compound, and is alkali metal carbonate, alkali metal hydroxide, alkali metal hydride, alkali metal. An alkoxide etc. are mentioned.
  • alkali metal carbonates such as potassium carbonate and sodium carbonate are preferable, and anhydrous alkali metal carbonates such as anhydrous potassium carbonate and anhydrous sodium carbonate are particularly preferably used.
  • the dihalogenodiphenyl compound is usually used in an amount of about 0.9 to 1.1 equivalents, preferably about 0.98 to 1.05 equivalents per equivalent of the dihydric phenol compound.
  • the base is used in an amount of about 1 equivalent or more, preferably 1.005 to 1.25 equivalents per equivalent of the phenolic hydroxyl group of the dihydric phenol compound.
  • the reaction solvent is used in an amount of about 0.1 to 10 parts by weight, preferably 0.5 to 3 parts by weight, based on 1 part by weight of the total of the dihydric phenol compound and the dihalogenodiphenyl compound.
  • the polycondensation reaction temperature is preferably about 140 to 340 ° C. When polycondensation is performed at a temperature higher than about 340 ° C., the decomposition reaction of the product polymer proceeds, so that there is a tendency that a high-purity aromatic polyether cannot be obtained. There is a tendency that a polymer having a molecular weight cannot be obtained.
  • the time for the polycondensation reaction varies depending on the type of dihydric phenol compound or dihalogenodiphenyl compound, the reaction temperature, etc., but is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • the polycondensation reaction is carried out by setting conditions from the above reaction conditions so as to achieve the target molecular weight. If the monohalogenodiphenyl compound and the monohydric phenol compound in the raw materials charged in the reactor are increased, the molecular weight is not lowered and the molecular weight is lowered.
  • the monohalogenodiphenyl compound is a compound having a halogenophenyl group and a phenyl group, and is contained in and mixed with the raw material dihalogenodiphenyl compound and diphenylsulfone used as a reaction solvent.
  • the monohalogenodiphenyl compound include monohalogenodiphenyl compounds having a sulfone group, for example, 4-halogenodiphenyl sulfones (the following formula) such as 4-chlorodiphenylsulfone and 4-bromodiphenylsulfone.
  • the monohydric phenol compound is a phenol compound having one phenolic hydroxyl group, and is contained and mixed in the raw material dihydric phenol compound.
  • Examples of the monohydric phenol compound include phenol and 4-hydroxydiphenyl sulfone.
  • the amount of monohalogenodiphenyl compound contained in the raw material charged into the reactor is 0.25 mol% or less, preferably 0.1 mol% or less of the dihalogenodiphenyl compound, and the amount of monohydric phenol compound is dihydric phenol compound.
  • the polycondensation reaction is carried out under the condition of 0.25 mol% or less, preferably 0.1 mol% or less, to prevent the molecular weight from being lowered, so that the target molecular weight can be almost achieved.
  • the reaction mixture obtained by the reaction contains a by-product salt that is a reaction product of a hydrogen halide eliminated by a polycondensation reaction and a base, a reaction solvent, and an aromatic polyether.
  • By-product salt is, for example, potassium chloride when hydrogen chloride is eliminated by a polycondensation reaction and potassium carbonate is used as a base.
  • the solidified reaction mixture is pulverized, and the pulverized reaction mixture is washed with water to remove by-product salts.
  • the reaction solvent is extracted by using a purified solvent having a boiling point lower than that of the reaction solvent and dissolving the reaction solvent but not the aromatic polyether to remove the reaction solvent.
  • Aromatic polyether is separated. Examples of such a purification solvent include methanol, ethanol, isopropyl alcohol, acetone, methyl ethyl ketone, and mixtures thereof.
  • the extraction solution obtained by extracting the reaction solvent with a purified solvent is distilled, the purified solvent with low boiling point and water are distilled off, and the reaction solvent is separated.
  • the separated purification solvent and reaction solvent are usually reused.
  • the reduced viscosity which is a measure of molecular weight, was measured. It shows that it is high molecular weight, so that the value of reduced viscosity is large.
  • the viscosity was measured at 25 ° C. using an Ostwald type viscosity tube.
  • the concentration of the polymer solution for measuring the viscosity was 1.0 g / 100 ml in an N, N-dimethylformamide (reagent special grade) solution.
  • the reduced viscosity (RV) is defined by the following formula (1).
  • Example 1 In a reaction vessel equipped with a stirrer, a nitrogen inlet tube, a thermometer, and a condenser with a receiver at the tip, 100.11 parts by weight of 4,4′-dihydroxydiphenylsulfone as a dihydric phenol compound, dihalogenodiphenyl compound As a reaction solvent, 119.23 parts by weight of 4,4′-dichlorodiphenylsulfone and 194.33 parts by weight of diphenylsulfone as a reaction solvent were charged.
  • the amount of monohalogenodiphenyl compound (total of 4-chlorodiphenylsulfone and 4-bromodiphenylsulfone) in the raw material is 0.05 parts by weight or less, and 0.05 mol% or less of 4,4′-dichlorodiphenylsulfone. there were.
  • the amount of the monohydric phenol compound (phenol) in the raw material was 0.02 parts by weight or less, and 0.05 mol% or less of 4,4′-dihydroxydiphenylsulfone.
  • the temperature was raised to 180 ° C. and dissolved while further circulating nitrogen in the reactor. Next, 57.5 parts by weight of anhydrous potassium carbonate was added.
  • the reaction solution was cooled to room temperature and solidified, and finely pulverized into a powder.
  • the powdery reaction mixture containing the obtained aromatic polyether, a by-product salt generated by the neutralization reaction of the base and hydrogen halide, and diphenyl sulfone was washed with warm water to remove the by-product salt.
  • the reaction mixture after removing the by-product salt was extracted with an acetone / methanol mixture. The extract was distilled and acetone, methanol and water were distilled off to obtain recovered diphenylsulfone.
  • Example 1 An aromatic polyether was produced in the same manner as in Example 1 except that diphenyl sulfone used in Example 1 was different from diphenyl sulfone having a monohalogenodiphenyl compound content.
  • the amount of monohalogenodiphenyl compound (total of 4-chlorodiphenylsulfone and 4-bromodiphenylsulfone) in the raw material was 0.39 parts by weight, and was 0.37 mol% of 4,4′-dichlorodiphenylsulfone.
  • the amount of the monohydric phenol compound (phenol) in the raw material was 0.02 parts by weight or less, and 0.05 mol% or less of 4,4′-dihydroxydiphenylsulfone.
  • the reduced viscosity of the obtained aromatic polyether was 0.400 dl / g.
  • Example 2 and Comparative Examples 2 to 4 After charging the raw materials in the same manner as in Example 1, 4-chlorodiphenyl sulfone (99.99%) was further added in 0.1 parts by weight (0.10 mol% of 4,4′-dichlorodiphenyl sulfone) (Example 2), 0.97 parts by weight (0.92 mol% of 4,4′-dichlorodiphenylsulfone) (Comparative Example 2), 1.94 parts by weight (1.85 mol% of 4,4′-dichlorodiphenylsulfone) ) (Comparative Example 3), 3.89 parts by weight (3.71 mol% of 4,4′-dichlorodiphenylsulfone) (Comparative Example 4) were added, and the aromatic polyether of Manufactured.
  • the reduced viscosity of the obtained aromatic polyether was 0.427 dl / g (Example 2), 0.351 dl / g (Comparative Example 2), 0.325 dl / g (Comparative Example 3), 0.291 dl / g, respectively. g (Comparative Example 4). Comparative Example 5 After the raw materials were charged in the same manner as in Example 1, 0.14 parts by weight of phenol (0.37 mol% of 4,4′-dihydroxydiphenyl sulfone) was further added. Ether was produced. The reduced viscosity of the obtained aromatic polyether was 0.403 dl / g.
  • an aromatic polyether having a target molecular weight can be more reliably produced.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)

Abstract

L'invention concerne un procédé de fabrication d'un polyéther aromatique consistant à mettre en réaction de polymérisation par condensation un composé de phénol dihydrique et un composé de dihalogéno diphényle en présence d'un solvant de réaction et d'une base. Ce procédé se caractérise en ce que la réaction de polymérisation par condensation se fait dans des conditions dans lesquelles, la quantité de composé monohalogéno diphényle de 4-chlorodiphénylesulfone, 4-bromodiphénylsulfone ou similaire contenue dans la substance de base, est égale ou inférieure à 0,25 mole %, de préférence égale ou inférieure à 0,1 mole %, du composé dihalogéno diphényle, et la quantité de composé de phénol monohydrique de phénol, 4-hydroxydiphénylsulfone ou similaire contenue dans la substance de base est égale ou inférieure à 0,25 mole %, de préférence égale ou inférieure à 0,1 mole %, du composé de phénol dihydrique.
PCT/JP2010/063593 2009-08-06 2010-08-04 Procédé de fabrication d'un polyéther aromatique WO2011016583A1 (fr)

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JP2009183161 2009-08-06
JP2009-183161 2009-08-06

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WO2011016583A1 true WO2011016583A1 (fr) 2011-02-10

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0632894A (ja) * 1992-07-10 1994-02-08 Ube Ind Ltd ポリアリールエーテルの製造方法
JPH06100689A (ja) * 1992-09-22 1994-04-12 Ube Ind Ltd ポリアリールエーテルの製造方法
JP2008248010A (ja) * 2007-03-29 2008-10-16 Sumitomo Chemical Co Ltd 重合度の測定方法および芳香族ポリエーテルの製造方法
JP2009138149A (ja) * 2007-12-10 2009-06-25 Sumitomo Chemical Co Ltd ポリエーテルスルホン系樹脂組成物及びその成形体
JP2010077185A (ja) * 2008-09-24 2010-04-08 Toray Ind Inc ヒドロキシフェニル末端基を有する芳香族ポリエーテルスルホンとその製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0632894A (ja) * 1992-07-10 1994-02-08 Ube Ind Ltd ポリアリールエーテルの製造方法
JPH06100689A (ja) * 1992-09-22 1994-04-12 Ube Ind Ltd ポリアリールエーテルの製造方法
JP2008248010A (ja) * 2007-03-29 2008-10-16 Sumitomo Chemical Co Ltd 重合度の測定方法および芳香族ポリエーテルの製造方法
JP2009138149A (ja) * 2007-12-10 2009-06-25 Sumitomo Chemical Co Ltd ポリエーテルスルホン系樹脂組成物及びその成形体
JP2010077185A (ja) * 2008-09-24 2010-04-08 Toray Ind Inc ヒドロキシフェニル末端基を有する芳香族ポリエーテルスルホンとその製造方法

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