WO2011004730A1 - Procédé de production de particules de polycarbonate aliphatique - Google Patents

Procédé de production de particules de polycarbonate aliphatique Download PDF

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Publication number
WO2011004730A1
WO2011004730A1 PCT/JP2010/061024 JP2010061024W WO2011004730A1 WO 2011004730 A1 WO2011004730 A1 WO 2011004730A1 JP 2010061024 W JP2010061024 W JP 2010061024W WO 2011004730 A1 WO2011004730 A1 WO 2011004730A1
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WO
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Prior art keywords
aliphatic polycarbonate
aliphatic
catalyst
polycarbonate particles
carbon dioxide
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Application number
PCT/JP2010/061024
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English (en)
Japanese (ja)
Inventor
藤本信貴
岡本匡史
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住友精化株式会社
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Application filed by 住友精化株式会社 filed Critical 住友精化株式会社
Priority to JP2011521888A priority Critical patent/JPWO2011004730A1/ja
Publication of WO2011004730A1 publication Critical patent/WO2011004730A1/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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/32—General preparatory processes using carbon dioxide
    • C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers

Definitions

  • the present invention relates to a method for producing aliphatic polycarbonate particles.
  • Global warming is caused by the increase in greenhouse gases such as carbon dioxide, chlorofluorocarbons and methane in the atmosphere, so reducing the atmospheric concentration of carbon dioxide, which has a high contribution to global warming, It is extremely important, and various studies such as emission regulations and immobilization are being carried out on a global scale.
  • epoxides such as ethylene oxide and propylene oxide are used as raw materials, and the resulting aliphatic polycarbonate has a problem that it has a low glass transition temperature and tends to agglomerate.
  • the resulting aliphatic polycarbonate is agglomerated, for example, when purifying the aliphatic polycarbonate, it is difficult for the cleaning liquid to penetrate the aliphatic polycarbonate, and it is difficult to remove impurities such as remaining catalyst and monomer. Problem arises.
  • a pulverizing step is required to obtain an appropriate particle size that is easy to handle.
  • the term “agglomerated” refers to a case where aliphatic polycarbonate particles are aggregated to form an aggregate having a particle diameter exceeding 2000 ⁇ m. Further, when the aliphatic polycarbonate is welded to form a lump-like lump, it is also defined as “lump-shaped”.
  • An object of the present invention is to provide a method for easily producing aliphatic polycarbonate particles using carbon dioxide and epoxide.
  • the present invention relates to a method for producing aliphatic polycarbonate particles as shown below.
  • Item 1 A method for producing aliphatic polycarbonate particles, comprising: a polymerization step in which carbon dioxide and epoxide are reacted in the presence of a metal catalyst; and a step of cooling the reaction solution containing the polymer obtained in the polymerization step to room temperature with stirring.
  • Item 2. Item 2. The method for producing aliphatic polycarbonate particles according to Item 1, wherein the metal catalyst is an organozinc catalyst.
  • Item 3. Item 3.
  • Item 4. Item 4.
  • the epoxide used in the polymerization step according to the present invention is not particularly limited as long as it is an epoxide that undergoes a polymerization reaction with carbon dioxide and becomes an aliphatic polycarbonate having a structure containing an aliphatic in the main chain.
  • ethylene oxide and propylene oxide are preferably used from the viewpoint of high polymerization reactivity with carbon dioxide.
  • these epoxides may be used alone or in combination of two or more.
  • Examples of the metal catalyst used in the polymerization step according to the present invention include an aluminum catalyst and a zinc catalyst.
  • a zinc catalyst is preferably used, and among zinc catalysts, an organic zinc catalyst is preferably used.
  • organic zinc catalyst examples include organic zinc catalysts such as zinc acetate, diethyl zinc and dibutyl zinc, primary amines, divalent phenols, divalent aromatic carboxylic acids, aromatic hydroxy acids, aliphatic dicarboxylic acids, Examples include an organic zinc catalyst obtained by reacting a compound such as an aliphatic monocarboxylic acid with a zinc compound.
  • organic zinc catalysts an organozinc catalyst obtained by reacting a zinc compound, an aliphatic dicarboxylic acid and an aliphatic monocarboxylic acid is preferable because it has higher polymerization activity.
  • an organic zinc catalyst obtained by reacting a zinc compound, an aliphatic dicarboxylic acid, and an aliphatic monocarboxylic acid will be described in more detail as an example of an embodiment of an organic zinc catalyst.
  • the zinc compound examples include inorganic zinc compounds such as zinc oxide, zinc hydroxide, zinc nitrate and zinc carbonate, and organic zinc compounds such as zinc acetate, diethyl zinc and dibutyl zinc.
  • inorganic zinc compounds such as zinc oxide, zinc hydroxide, zinc nitrate and zinc carbonate
  • organic zinc compounds such as zinc acetate, diethyl zinc and dibutyl zinc.
  • zinc oxide and zinc hydroxide are preferably used from the viewpoint of obtaining an organic zinc catalyst having high catalytic activity.
  • These zinc compounds may be used alone or in combination of two or more.
  • aliphatic dicarboxylic acid examples include malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid and the like.
  • glutaric acid and adipic acid are preferably used from the viewpoint of obtaining an organozinc catalyst having high catalytic activity.
  • these aliphatic dicarboxylic acids may be used alone or in combination of two or more.
  • the proportion of the aliphatic dicarboxylic acid used is usually preferably from 0.1 to 1.5 mol, more preferably from 0.5 to 1.0 mol, based on 1 mol of the zinc compound.
  • the use ratio of the aliphatic dicarboxylic acid is less than 0.1 mol, the reaction with the zinc compound may not easily proceed.
  • the usage-amount of aliphatic dicarboxylic acid exceeds 1.5 mol, in the activity of the obtained organozinc catalyst, there is a possibility that it may not be economical because there is no effect corresponding to the amount used.
  • aliphatic monocarboxylic acid examples include formic acid, acetic acid, propionic acid and the like.
  • formic acid and acetic acid are preferably used from the viewpoint of obtaining an organozinc catalyst having high activity.
  • These aliphatic monocarboxylic acids may be used alone or in combination of two or more.
  • the proportion of the aliphatic monocarboxylic acid used is preferably 0.0001 to 0.1 mol, more preferably 0.001 to 0.05 mol, per 1 mol of the aliphatic dicarboxylic acid.
  • the proportion of the aliphatic monocarboxylic acid used is less than 0.0001 mol, the resulting organozinc catalyst has a structure containing a carboxylic acid group at the end, which may result in a less active organozinc catalyst. There is.
  • the usage-amount of aliphatic monocarboxylic acid exceeds 0.1 mol, in the activity of the obtained organozinc catalyst, there exists a possibility that it may not become economical without the effect corresponding to the usage-amount.
  • the method of reacting the zinc compound, the aliphatic dicarboxylic acid and the aliphatic monocarboxylic acid is not particularly limited, and these may be reacted simultaneously, or the aliphatic dicarboxylic acid or the aliphatic monocarboxylic acid may be reacted. After reacting either one of the carboxylic acids and the zinc compound first, the reaction product and the other may be reacted successively.
  • a solvent may be used from the viewpoint of smoothly performing the reaction.
  • the solvent is not particularly limited as long as it does not inhibit the reaction, and examples thereof include aromatic hydrocarbon solvents such as benzene, toluene and xylene, ether solvents such as diethyl ether, tetrahydrofuran and dioxane, and dimethyl carbonate. And carbonate solvents such as diethyl carbonate and propylene carbonate, acetonitrile, dimethylformamide, dimethyl sulfoxide, hexamethylphosphotriamide and the like.
  • aromatic hydrocarbon solvents such as benzene, toluene, and xylene are preferably used from the viewpoint of obtaining particulate aliphatic polycarbonate and from the viewpoint of easy reuse of the solvent.
  • the amount of the solvent used is preferably 500 to 10,000 parts by mass with respect to 100 parts by mass of the zinc compound from the viewpoint of smoothly performing the reaction.
  • the reaction temperature at the time of reacting the zinc compound, aliphatic dicarboxylic acid and aliphatic monocarboxylic acid is not particularly limited, but is preferably 20 to 110 ° C., more preferably 50 to 100 ° C. preferable. Further, the reaction time varies depending on the reaction temperature and cannot be generally specified, but it is usually preferably 1 to 20 hours.
  • the organozinc catalyst thus obtained is used in a polymerization step in which carbon dioxide and epoxide are reacted with each other isolated by a conventional method such as filtration after the completion of the reaction or without being isolated. Can do.
  • the organozinc catalyst when it is used without being isolated and contained in the reaction solution, it sufficiently removes water that may adversely affect the reaction between carbon dioxide and epoxide. It is preferable to keep it.
  • the amount of the metal catalyst used in the polymerization step according to the present invention is preferably 0.001 to 20 parts by mass, more preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the epoxide. .
  • the usage-amount of a metal catalyst is less than 0.001 mass part, there exists a possibility that a polymerization reaction may become difficult to advance.
  • the usage-amount of a metal catalyst exceeds 20 mass parts, there exists a possibility that there may be no effect corresponding to a usage-amount and it may become economical.
  • the reaction solvent used as necessary in the polymerization step according to the present invention is not particularly limited, and various organic solvents can be used.
  • the organic solvent include aliphatic hydrocarbon solvents such as pentane, hexane, octane, decane, and cyclohexane, aromatic hydrocarbon solvents such as benzene, toluene, and xylene, chloromethane, Methylene dichloride, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane, ethyl chloride, trichloroethane, 1-chloropropane, 2-chloropropane, 1-chlorobutane, 2-chlorobutane, 1-chloro-2-methylpropane
  • halogenated hydrocarbon solvents such as chlorobenzene and bromobenzene, and carbonate solvents such as dimethyl carbonate, diethyl carbonate and propylene carbon
  • the amount of the reaction solvent used is preferably 500 to 10,000 parts by mass with respect to 100 parts by mass of the epoxide, from the viewpoint of facilitating the reaction.
  • the method of reacting carbon dioxide and epoxide in the presence of a metal catalyst is not particularly limited.
  • the epoxide, the metal catalyst, and, if necessary, the reaction solvent in an autoclave After mixing and mixing, carbon dioxide is injected and reacted.
  • the working pressure of carbon dioxide used in the polymerization step according to the present invention is not particularly limited, but is usually preferably 0.1 to 20 MPa, more preferably 0.1 to 10 MPa, and more preferably 0.1 to 10 MPa. More preferably, it is 5 MPa.
  • the use pressure of carbon dioxide exceeds 20 MPa, there is a possibility that the effect corresponding to the use pressure may not be obtained and it may not be economical.
  • the polymerization reaction temperature in the polymerization step according to the present invention is not particularly limited, but is preferably 30 to 100 ° C, and more preferably 40 to 80 ° C. When the polymerization reaction temperature is less than 30 ° C., the polymerization reaction may take a long time. Moreover, when a polymerization reaction temperature exceeds 100 degreeC, a side reaction occurs and there exists a possibility that a yield may fall.
  • the polymerization reaction time varies depending on the polymerization reaction temperature and cannot be generally specified, but it is usually preferably 2 to 40 hours.
  • the present invention is characterized by having a step of cooling the reaction solution containing the polymer obtained in the polymerization step to room temperature (15 to 28 ° C.) with stirring following the polymerization reaction step of carbon dioxide and epoxide. To do.
  • the speed at which the reaction solution containing the polymer is agitated cannot be generally determined depending on the size and shape of the reaction apparatus used, the shape of the stirring blade used, etc., for example, when a twin star type stirring blade is used.
  • the stirring rotation speed is preferably 25 to 500 r / min. If it is the range of the said stirring speed, it can obtain as a particulate form, without a polymer being united.
  • the cooling rate is not generally determined depending on the size of the reaction apparatus to be used, but is preferably 0.1 to 10 ° C./min. If it is the range of the said cooling rate, since a polymer will unite and it will become difficult to agglomerate, it is preferable.
  • the cooling method is not particularly limited, and examples include cooling with a refrigerant and air cooling.
  • the aliphatic polycarbonate particles according to the present invention can be obtained by filtration, washing with a solvent or the like if necessary, and drying.
  • the aliphatic polycarbonate particles thus obtained are particles having an average particle diameter of 50 to 2000 ⁇ m, and they are united to form a lump with a particle diameter exceeding 2000 ⁇ m or a welded lump. Since it is not a lump, it is easy to handle and process, and is suitably used as a binder resin used in thick film pastes such as glass pastes, conductive pastes, phosphor pastes, and ceramics.
  • the average particle diameter can be measured using LASER DIFFRATION PARTICIZE SIZE ANALYZER (“SALD-200” manufactured by Shimadzu Corporation).
  • aliphatic polycarbonate particles can be easily provided.
  • Example 1 After the inside of the system of 1 L autoclave (cylinder inner diameter 95 mm, height 240 mm) equipped with a stirrer, a twin star type stirring blade (blade diameter 50 mm), a gas introduction tube, and a thermometer was previously replaced with a nitrogen atmosphere, Production Example 1 The reaction solution containing the organozinc catalyst obtained in the above step (8.0 mL) (containing 1.0 g of the organozinc catalyst), 131 g (200 mL) of hexane, and 35.2 g (0.80 mol) of ethylene oxide were charged.
  • the obtained polyethylene carbonate particles could be identified from the following physical properties. IR (KBr): 1740, 1447, 1386, 1217, 1029, 785 (cm ⁇ 1 )
  • the average particle diameter of the obtained polyethylene carbonate particles was measured by LASER DIFFRACTION PARTLE SIZE ANALYZER (manufactured by Shimadzu Corporation, “SALD-200”), and was 550 ⁇ m.
  • Example 2 In Example 1, instead of 35.2 g (0.80 mol) of ethylene oxide, 81.3 g of polypropylene carbonate particles were obtained in the same manner as in Example 1 except that 46.4 g (0.80 mol) of propylene oxide was used. Obtained.
  • the obtained polypropylene carbonate particles could be identified from the following physical properties. IR (KBr): 1742, 1456, 1381, 1229, 1069, 787 (cm ⁇ 1 )
  • the average particle diameter of the obtained polypropylene carbonate particles was 250 ⁇ m when measured by LASER DIFFRACTION PARTLE SIZE ANALYZER (manufactured by Shimadzu Corporation, “SALD-200”).
  • Example 1 In Example 1, after completion of the polymerization reaction, the pressure was released and the mixture was cooled for 70 minutes from 60 ° C. to 25 ° C. without stirring. 68.5 g of converted polyethylene carbonate was obtained.

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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)
  • Polyesters Or Polycarbonates (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention porte sur un procédé pour produire de façon aisée des particules de polycarbonate aliphatique à l'aide de dioxyde de carbone et un époxyde. Le procédé comprend une étape de polymérisation consistant à faire réagir du dioxyde de carbone avec un époxyde en présence d'un catalyseur métallique et une étape de refroidissement du fluide réactionnel à teneur en polymère obtenu par l'étape de polymérisation jusqu'à une température ambiante sous agitation. Etant donné que les particules de polycarbonate aliphatique obtenues par les procédés ne sont pas des morceaux ayant coalescé, les particules de polycarbonate aliphatique sont faciles à manipuler et à traiter, et de ce fait sont appropriées pour être utilisées comme résine liante pour des pâtes en couche épaisse telles qu'une pâte de verre, une pâte conductrice ou une pâte fluorescente, la céramique ou similaires.
PCT/JP2010/061024 2009-07-07 2010-06-29 Procédé de production de particules de polycarbonate aliphatique WO2011004730A1 (fr)

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JP2011521888A JPWO2011004730A1 (ja) 2009-07-07 2010-06-29 脂肪族ポリカーボネート粒子の製造方法

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JP2009160751 2009-07-07

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8247520B2 (en) 2008-09-08 2012-08-21 Novomer, Inc. Polycarbonate polyol compositions and methods
JPWO2012128028A1 (ja) * 2011-03-18 2014-07-24 住友精化株式会社 金属ペースト組成物
WO2015072815A1 (fr) * 2013-11-18 2015-05-21 주식회사 엘지화학 Catalyseur organozincique, son procédé de préparation, et procédé pour la préparation d'une résine polyalkylène carbonate en faisant appel à celui-ci
US9447236B2 (en) 2013-05-27 2016-09-20 Lg Chem, Ltd. Method of manufacturing polyalkylene carbonate
JP2016530301A (ja) * 2013-10-30 2016-09-29 エルジー・ケム・リミテッド 有機亜鉛触媒の製造方法およびポリアルキレンカーボネート樹脂の製造方法
US9732187B2 (en) 2013-11-18 2017-08-15 Lg Chem, Ltd. Manufacturing method of polyalkylene carbonate resin
US9803048B2 (en) 2013-11-04 2017-10-31 Lg Chem, Ltd. Organic zinc catalyst and preparation method thereof
US10047196B2 (en) 2013-11-18 2018-08-14 Lg Chem, Ltd. Organic zinc catalyst, and manufacturing method thereof and manufacturing method of polyalkylene carbonate resin using the same (as amended)
US11180609B2 (en) 2018-08-02 2021-11-23 Saudi Aramco Technologies Company Sustainable polymer compositions and methods

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JP2007177026A (ja) * 2005-12-27 2007-07-12 Nippon Ester Co Ltd ポリエステル系水性分散体用樹脂
JP2007302731A (ja) * 2006-05-09 2007-11-22 Sumitomo Seika Chem Co Ltd 有機亜鉛触媒およびそれを用いたポリアルキレンカーボネートの製造方法
JP2008024726A (ja) * 2006-07-18 2008-02-07 Unitika Ltd ポリエステル樹脂水性分散体

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007177026A (ja) * 2005-12-27 2007-07-12 Nippon Ester Co Ltd ポリエステル系水性分散体用樹脂
JP2007302731A (ja) * 2006-05-09 2007-11-22 Sumitomo Seika Chem Co Ltd 有機亜鉛触媒およびそれを用いたポリアルキレンカーボネートの製造方法
JP2008024726A (ja) * 2006-07-18 2008-02-07 Unitika Ltd ポリエステル樹脂水性分散体

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9809678B2 (en) 2008-09-08 2017-11-07 Saudi Aramco Technologies Company Polycarbonate polyol compositions and methods
US8470956B2 (en) 2008-09-08 2013-06-25 Novomer, Inc. Polycarbonate polyol compositions and methods
US8604155B2 (en) 2008-09-08 2013-12-10 Novomer, Inc. Polycarbonate polyol compositions and methods
US8921508B2 (en) 2008-09-08 2014-12-30 Novomer, Inc. Polycarbonate polyol compositions and methods
US11535706B2 (en) 2008-09-08 2022-12-27 Saudi Aramco Technologies Company Polycarbonate polyol compositions and methods
US9376531B2 (en) 2008-09-08 2016-06-28 Novomer, Inc. Polycarbonate polyol compositions and methods
US8247520B2 (en) 2008-09-08 2012-08-21 Novomer, Inc. Polycarbonate polyol compositions and methods
US10836859B2 (en) 2008-09-08 2020-11-17 Saudi Aramco Technologies Company Polycarbonate polyol compositions and methods
US10301426B2 (en) 2008-09-08 2019-05-28 Saudi Aramco Technologies Company Polycarbonate polyol compositions and methods
JPWO2012128028A1 (ja) * 2011-03-18 2014-07-24 住友精化株式会社 金属ペースト組成物
US9414487B2 (en) 2011-03-18 2016-08-09 Sumitomo Seika Chemicals Co., Ltd. Metal paste composition
US9447236B2 (en) 2013-05-27 2016-09-20 Lg Chem, Ltd. Method of manufacturing polyalkylene carbonate
US9751981B2 (en) 2013-10-30 2017-09-05 Lg Chem, Ltd. Manufacturing method of organic zinc catalyst and manufacturing method of polyalkylene carbonate resin
JP2016530301A (ja) * 2013-10-30 2016-09-29 エルジー・ケム・リミテッド 有機亜鉛触媒の製造方法およびポリアルキレンカーボネート樹脂の製造方法
US9803048B2 (en) 2013-11-04 2017-10-31 Lg Chem, Ltd. Organic zinc catalyst and preparation method thereof
US10047196B2 (en) 2013-11-18 2018-08-14 Lg Chem, Ltd. Organic zinc catalyst, and manufacturing method thereof and manufacturing method of polyalkylene carbonate resin using the same (as amended)
US9732187B2 (en) 2013-11-18 2017-08-15 Lg Chem, Ltd. Manufacturing method of polyalkylene carbonate resin
WO2015072815A1 (fr) * 2013-11-18 2015-05-21 주식회사 엘지화학 Catalyseur organozincique, son procédé de préparation, et procédé pour la préparation d'une résine polyalkylène carbonate en faisant appel à celui-ci
US11180609B2 (en) 2018-08-02 2021-11-23 Saudi Aramco Technologies Company Sustainable polymer compositions and methods

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TW201105707A (en) 2011-02-16

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