JP5927184B2 - ポリアルキレンオキシド粒子及びその製造方法 - Google Patents
ポリアルキレンオキシド粒子及びその製造方法 Download PDFInfo
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- JP5927184B2 JP5927184B2 JP2013517973A JP2013517973A JP5927184B2 JP 5927184 B2 JP5927184 B2 JP 5927184B2 JP 2013517973 A JP2013517973 A JP 2013517973A JP 2013517973 A JP2013517973 A JP 2013517973A JP 5927184 B2 JP5927184 B2 JP 5927184B2
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- 239000002245 particle Substances 0.000 title claims description 105
- 229920000233 poly(alkylene oxides) Polymers 0.000 title claims description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims description 81
- 238000006116 polymerization reaction Methods 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 125000001931 aliphatic group Chemical group 0.000 claims description 31
- 150000005846 sugar alcohols Polymers 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000843 powder Substances 0.000 description 17
- 239000006185 dispersion Substances 0.000 description 16
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 150000003752 zinc compounds Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000011481 absorbance measurement Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000007561 laser diffraction method Methods 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- TVMNKLXCVINVQG-UHFFFAOYSA-N C1CCC1[Zn]C1CCC1 Chemical compound C1CCC1[Zn]C1CCC1 TVMNKLXCVINVQG-UHFFFAOYSA-N 0.000 description 1
- QQTGJVBUIOTPGZ-UHFFFAOYSA-N CCC[Zn]CCC Chemical compound CCC[Zn]CCC QQTGJVBUIOTPGZ-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
- MKRVHLWAVKJBFN-UHFFFAOYSA-N diphenylzinc Chemical compound C=1C=CC=CC=1[Zn]C1=CC=CC=C1 MKRVHLWAVKJBFN-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- JJAIIULJXXEFLV-UHFFFAOYSA-N pentane-2,3,4-triol Chemical compound CC(O)C(O)C(C)O JJAIIULJXXEFLV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/266—Metallic elements not covered by group C08G65/2648 - C08G65/2645, or compounds thereof
-
- 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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
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- Medicinal Chemistry (AREA)
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- Polyethers (AREA)
- Catalysts (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
製造例で得られた触媒及び実施例で得られたポリアルキレンオキシド粒子を、以下の方法に従って評価した。
触媒の平均粒子径は下記レーザー回折法により測定される。
キャリアとしてヘキサンを使用して、触媒スラリーを作製した。レーザー回折式粒度分布測定装置(島津製作所社製、型番:SALD−7100)に上記触媒スラリーを循環させ、触媒の平均粒子径を測定した。
ポリアルキレンオキシド粒子の粒度分布及び質量平均粒子径は下記網目通過式分級法により測定及び算出される。
ポリアルキレンオキシド粒子100gと、滑剤として非晶質シリカ(株式会社トクヤマ製、トクシールNP)2gとを混合した。
JIS Z 8801−1標準篩として、目開き500μmの篩、目開き300μmの篩、目開き250μmの篩、目開き180μmの篩、目開き150μmの篩、目開き106μmの篩、及び目開き75μmの篩を上からこの順で受皿の上に重ね合わせた。
最上段に配置された目開き500μmの篩に、ポリアルキレンオキシド粒子と非晶質シリカとの混合物を入れた。篩をロータップ式振とう器を用いて20分間振とうさせることにより、混合物を分級した。
分級後、各篩上に残ったポリアルキレンオキシド粒子の質量を測定し、各質量の全量に対する質量百分率を計算した。目開きの大きい篩から順に質量百分率を積算し、篩の目開きと、篩上に残ったポリアルキレンオキシド粒子の質量百分率の積算値(積算質量百分率)との関係を、対数確率紙にプロットした。紙面上のプロットを直線で結び、積算質量百分率が50質量%のときの篩の目開きの値を、ポリアルキレンオキシド粒子の質量平均粒子径とした。
また、目開き106μmの篩、目開き75μmの篩及び受皿上に残ったポリアルキレンオキシド粒子の質量百分率の合計値を、150μm未満の粒子径を有する粒子の質量百分率として算出した。
ポリ瓶に、ポリアルキレンオキシド粒子20gと青色1号(ダイワ化成株式会社製)100mgとを加え、これらをクロスロータリー混合機(株式会社明和工業製)を用いて30分間混合した。
得られた混合物を、任意の4ヶ所から200mgずつ測り取り、それぞれを500gの水に溶解させた。4つの溶解液をそれぞれ光路長1cmの石英セルに入れ、分光光度計(島津製作所社製、型番:UV−3150)により波長629nmにおける吸光度を測定した。
4つの吸光度測定値及びそれらの平均値から、以下の数式に基づいてそれぞれの測定値の誤差率を算出した。得された誤差率から、ポリアルキレンオキシド粒子と粉体との混合における均一度(粉体混合性)を、以下の基準にしたがって評価した。
誤差率=|吸光度測定値−平均値|/平均値×100 (%)
A:4つのうち最も大きい誤差率が10%未満
B:4つのうち最も大きい誤差率が10%以上15%未満
C:4つのうち最も大きい誤差率が15%以上25%未満
D:4つのうち最も大きい誤差率が25%以上
還流冷却器、滴下ロート、窒素ガス導入管、及び攪拌機としての翼径53mmの4枚の(45度傾斜)パドル翼を有する攪拌翼が装着された、内径80mm、容積500mLのフラスコを準備した。
先端周速を0.97m/秒(攪拌回転速度350rpm)から1.94m/秒(攪拌回転速度700rpm)に変更した以外は、製造例1と同様の操作を行い、有機亜鉛触媒(触媒B)を3質量%含む分散液302gを得た。得られた触媒Bの平均粒子径の測定結果を表1に示す。
エタノールの使用量を17.6g(382ミリモル)から22.8g(495ミリモル)に変更した以外は、製造例2と同様の操作を行い、有機亜鉛触媒(触媒C)を3質量%含む分散液302gを得た。得られた触媒Cの平均粒子径の測定結果を表1に示す。
先端周速を0.97m/秒(攪拌回転速度350rpm)から3.33m/秒(攪拌回転速度1200rpm)に変更し、エタノールの使用量を17.6g(382ミリモル)から29.0g(629ミリモル)に変更した以外は、製造例1と同様の操作を行い、有機亜鉛触媒(触媒D)を3質量%含む分散液302gを得た。得られた触媒Dの平均粒子径の測定結果を表1に示す。
先端周速を0.97m/秒(攪拌回転速度350rpm)から0.55m/秒(攪拌回転速度200rpm)に変更した以外は、製造例1と同様の操作を行い、有機亜鉛触媒(触媒E)を3質量%含む分散液302gを得た。得られた触媒Eの平均粒子径の測定結果を表1に示す。
滴下ロート、窒素ガス導入管、及び翼径47mmのいかり型パドル翼を有する攪拌翼を装着した、内径94mm、容積1Lの耐圧反応容器を準備した。
触媒Aの分散液を触媒Bの分散液に変更した以外は、実施例1と同様にして、ポリエチレンオキシド粒子80.7gを得た。得られたポリエチレンオキシド粒子の収率は、エチレンオキシドに対して99.6質量%であった。得られたポリエチレンオキシド粒子について、質量平均粒子径及び粉体混合性の評価を行った。評価結果を表2及び表3に示す。
触媒Aの分散液を触媒Cの分散液に変更した以外は、実施例1と同様にして、ポリエチレンオキシド粒子80.3gを得た。得られたポリエチレンオキシド粒子の収率は、エチレンオキシドに対して99.1質量%であった。得られたポリエチレンオキシド粒子について、質量平均粒子径及び粉体混合性の評価を行った。評価結果を表2及び表3に示す。
触媒Aの分散液を触媒Dの分散液に変更した以外は、実施例1と同様にして、ポリエチレンオキシド粒子80.8gを得た。得られたポリエチレンオキシド粒子の収率は、エチレンオキシドに対して99.7質量%であった。得られたポリエチレンオキシド粒子について、質量平均粒子径及び粉体混合性の評価を行った。評価結果を表2及び表3に示す。
触媒Aの分散液を触媒Eの分散液に変更した以外は、実施例1と同様にして、ポリエチレンオキシド粒子80.4gを得た。得られたポリエチレンオキシド粒子の収率は、エチレンオキシドに対して99.3質量%であった。得られたポリエチレンオキシド粒子について、質量平均粒子径及び粉体混合性の評価を行った。評価結果を表2及び表3に示す。
Claims (2)
- 重合溶媒及び該重合溶媒中に分散した触媒を含む重合液中で、アルキレンオキシドを重合させて、ポリアルキレンオキシド粒子を生成させる工程を備え、
前記触媒の平均粒子径が5〜25μmであり、
前記触媒が有機亜鉛触媒であり、前記有機亜鉛触媒が、有機亜鉛化合物を脂肪族多価アルコール及び一価アルコールと反応させて粒子状の反応生成物を生成させる工程を含む方法により得ることのできる粒子状の反応生成物である、ポリアルキレンオキシド粒子の製造方法。 - 前記重合液が、前記アルキレンオキシド1モルに対して0.00005モル以上の前記触媒を含む、請求項1に記載の製造方法。
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