JP5945829B2 - 連続乳化重合方法 - Google Patents
連続乳化重合方法 Download PDFInfo
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- JP5945829B2 JP5945829B2 JP2013501867A JP2013501867A JP5945829B2 JP 5945829 B2 JP5945829 B2 JP 5945829B2 JP 2013501867 A JP2013501867 A JP 2013501867A JP 2013501867 A JP2013501867 A JP 2013501867A JP 5945829 B2 JP5945829 B2 JP 5945829B2
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- 238000010556 emulsion polymerization method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 32
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- 239000003999 initiator Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 17
- 239000000839 emulsion Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 239000002994 raw material Substances 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 10
- 238000009826 distribution Methods 0.000 claims description 7
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 2
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- 239000000047 product Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000012062 aqueous buffer Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- -1 Vinyl halides Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
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- 239000012467 final product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010327 methods by industry Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical class CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000003703 image analysis method Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000005029 sieve analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
- C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
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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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerisation Methods In General (AREA)
Description
の均一サイズの液滴のみからなる。
[A)連続方式(実施例1〜3)]
図1は、実施例1〜3に使用された構成を示すものである。2つの撹拌槽1、2に、2つの独立したストリームが設けられる。2つのストリームは無脈動ポンプ3、4を使用してミキサー7へ送られる。それぞれのポンプの流量を制御するために、各供給ラインに流量計5、6が設置される。ミキサー7で作られたエマルションは、ジャケット付チューブ型反応器9と連結されたフロー式マイクロ波8へ直接送られる。チューブ型反応器9を出た反応懸濁液は、ジャケット付反応器10で集められる。全てのジャケット付装置は、反応の必要性に応じてそれぞれ加熱又は冷却するための手段を有している。
比較例4には、図2に示された構成が使用される。図1との違いは、フロー式マイクロ波が設置されていないことのみである。
2枚羽根スターラーを備えた1Lの実験室用ガラス製反応容器に、アクリル酸メチル誘導体、ジビニルベンゼン、及びジエン(モル比92:3:5)を入れる。モノマー溶液に、0.1%のラジカル開始剤を入れ、混合物ができるまで撹拌する。この有機反応混合物に、Na2HPO4、NaH2PO4、NaCl(1w/w%、0.07w/w%、4w/w%)とポリビニルアルコール(MW85000〜124000、1.1w/w%)とからなる水性緩衝液を添加し、反応容器の撹拌速度を450RPMに調整してエマルションを作成する。55℃まで加熱した後、8℃/時間勾配を特徴とする温度プログラムを開始して、ポリマー連鎖反応の開始を制御できるようにする。反応混合物を80℃で5時間保った後、生成物をろ過、水洗する。真空で乾燥することによって生成物が得られる。
Claims (8)
- 少なくとも2つの非相溶性の出発原料フローが混合装置の中で混合されるポリマーの製造方法であって、1つ又はそれ以上のモノマーと任意選択的に添加される1つ又はそれ以上のラジカル開始剤とが同じ出発原料フロー又は別個の出発原料フローに存在し、前記混合装置が、前記出発原料フローから、平均液滴サイズが1μmから2000μmであるエマルションを生成し、前記混合装置中の前記原料フローの温度は前記1つ又はそれ以上のラジカル開始剤の開始温度よりも下に、もしくは前記モノマーの重合温度又は架橋温度よりも下に維持され、前記混合された原料フローは、その後、前記モノマーの重合を開始するためにマイクロ波フロー式加熱器で加熱された後、1つ又はそれ以上の追加的な反応器を通る、ポリマーの製造方法。
- 前記混合装置中の前記原料フローの前記温度が−10℃から60℃の間に保たれる、請求項1に記載の方法。
- 前記マイクロ波フロー式加熱器中の前記温度が40℃から120℃の間に保たれる、請求項1又は2に記載の方法。
- 前記混合装置が、変動係数が1未満の粒度分布である前記エマルションを生成する、請求項1〜3のいずれか1項に記載の方法。
- 前記追加的な反応器がチューブ型反応器である、請求項1〜4のいずれか1項に記載の方法。
- 等温的温度プロファイル又は温度勾配が、前記マイクロ波フロー式加熱器、及び1つ又はそれ以上の前記追加的な反応器を有する工程に沿って形成される、請求項1〜5のいずれか1項に記載の方法。
- 前記方法における前記混合された原料フローが、レイノルド数100未満の層流である、請求項1〜6のいずれか1項に記載の方法。
- 前記装置と前記反応器が、最初に混合装置、2番目にマイクロ波フロー式加熱器、3番目に1つ又はそれ以上の追加的な反応器、の順に連結された、請求項1〜7のいずれか1項に記載の方法のための装置。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10158997.6 | 2010-04-01 | ||
EP10158997 | 2010-04-01 | ||
PCT/EP2011/055129 WO2011121124A1 (en) | 2010-04-01 | 2011-04-01 | Process for continuous emulsion polymerization |
Publications (2)
Publication Number | Publication Date |
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JP2013523933A JP2013523933A (ja) | 2013-06-17 |
JP5945829B2 true JP5945829B2 (ja) | 2016-07-05 |
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JP2013501867A Active JP5945829B2 (ja) | 2010-04-01 | 2011-04-01 | 連続乳化重合方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9296851B2 (ja) |
EP (1) | EP2552970B1 (ja) |
JP (1) | JP5945829B2 (ja) |
CN (1) | CN102834419B (ja) |
ES (1) | ES2522842T3 (ja) |
HK (1) | HK1179284A1 (ja) |
WO (1) | WO2011121124A1 (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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GB0523245D0 (en) * | 2005-11-15 | 2005-12-21 | Nitech Solutions Ltd | Improved apparatus and method for applying oscillatory motion |
GB0614810D0 (en) * | 2006-07-25 | 2006-09-06 | Nitech Solutions Ltd | Improved apparatus and method for maintaining consistently mixed materials |
JP5956232B2 (ja) * | 2012-04-24 | 2016-07-27 | 住友精化株式会社 | 吸水性樹脂の製造方法 |
CN105143276B (zh) * | 2013-04-16 | 2018-05-25 | 巴斯夫欧洲公司 | 制备基于c3-c8单烯属不饱和单-或二羧酸或其酸酐和盐的高度支化聚合物的连续方法 |
US9481764B1 (en) | 2015-10-13 | 2016-11-01 | The Boeing Company | Flow reactor synthesis of polymers |
CN106478882A (zh) * | 2016-11-30 | 2017-03-08 | 黄河三角洲京博化工研究院有限公司 | 一种微波法合成的高固含量丁苯乳胶及其制备方法 |
EP4335544A3 (en) | 2019-05-29 | 2024-06-12 | Saudi Arabian Oil Company | Flow synthesis of polymer nanoparticles |
US11566165B2 (en) | 2019-05-30 | 2023-01-31 | Saudi Arabian Oil Company | Polymers and nanoparticles for flooding |
CN110156924A (zh) * | 2019-05-31 | 2019-08-23 | 东华大学 | 一种微波辐射法制备含氟织物拒水拒油整理剂的方法 |
US11773715B2 (en) | 2020-09-03 | 2023-10-03 | Saudi Arabian Oil Company | Injecting multiple tracer tag fluids into a wellbore |
US11660595B2 (en) | 2021-01-04 | 2023-05-30 | Saudi Arabian Oil Company | Microfluidic chip with multiple porosity regions for reservoir modeling |
US11534759B2 (en) | 2021-01-22 | 2022-12-27 | Saudi Arabian Oil Company | Microfluidic chip with mixed porosities for reservoir modeling |
US12000278B2 (en) | 2021-12-16 | 2024-06-04 | Saudi Arabian Oil Company | Determining oil and water production rates in multiple production zones from a single production well |
Family Cites Families (11)
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AU3144697A (en) * | 1996-05-30 | 1998-01-05 | Shell Oil Company | Process to prepare low density porous cross-linked polymeric materials |
DE19816886C2 (de) | 1998-04-17 | 2001-06-07 | Axiva Gmbh | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Polymerisaten |
AU3733800A (en) * | 1999-03-09 | 2000-09-28 | Symyx Technologies, Inc. | Controlled free radical emulsion and water-based polymerizations and seeded methodologies |
JP4527384B2 (ja) | 2002-12-06 | 2010-08-18 | 綜研化学株式会社 | マイクロチャンネルを用いた着色球状粒子の製造方法、およびその製造方法に用いるマイクロチャンネル式製造装置 |
DE10301874A1 (de) | 2003-01-17 | 2004-07-29 | Celanese Emulsions Gmbh | Verfahren und Vorrichtung zur Herstellung von Emulsionspolymerisaten |
JP2008533222A (ja) * | 2005-03-10 | 2008-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 作用物質を含有する水性ポリマー分散液、それを製造する方法、およびその使用法 |
JP5040083B2 (ja) * | 2005-08-22 | 2012-10-03 | 日油株式会社 | コア−シェル型ポリマー粒子の製造方法 |
JP5116334B2 (ja) * | 2006-06-29 | 2013-01-09 | 三洋化成工業株式会社 | 高単分散微粒子の製造方法 |
JP2009029984A (ja) * | 2007-07-30 | 2009-02-12 | Konica Minolta Business Technologies Inc | 高分子樹脂粒子の連続製造装置及び高分子樹脂粒子の連続製造方法 |
JP5020001B2 (ja) * | 2007-08-31 | 2012-09-05 | 積水化成品工業株式会社 | スチレン系樹脂粒子の製造方法 |
JP2009079106A (ja) * | 2007-09-26 | 2009-04-16 | Sanyo Chem Ind Ltd | 多層構造粒子の製造方法 |
-
2011
- 2011-04-01 US US13/637,484 patent/US9296851B2/en active Active
- 2011-04-01 CN CN201180017879.5A patent/CN102834419B/zh active Active
- 2011-04-01 WO PCT/EP2011/055129 patent/WO2011121124A1/en active Application Filing
- 2011-04-01 ES ES11713240.7T patent/ES2522842T3/es active Active
- 2011-04-01 EP EP11713240.7A patent/EP2552970B1/en active Active
- 2011-04-01 JP JP2013501867A patent/JP5945829B2/ja active Active
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2013
- 2013-06-11 HK HK13106890.3A patent/HK1179284A1/zh unknown
Also Published As
Publication number | Publication date |
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US20130123427A1 (en) | 2013-05-16 |
US9296851B2 (en) | 2016-03-29 |
CN102834419A (zh) | 2012-12-19 |
CN102834419B (zh) | 2015-10-21 |
ES2522842T3 (es) | 2014-11-18 |
JP2013523933A (ja) | 2013-06-17 |
EP2552970B1 (en) | 2014-07-30 |
EP2552970A1 (en) | 2013-02-06 |
WO2011121124A1 (en) | 2011-10-06 |
HK1179284A1 (zh) | 2013-09-27 |
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