JP2014519534A5 - - Google Patents
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- Publication number
- JP2014519534A5 JP2014519534A5 JP2014509633A JP2014509633A JP2014519534A5 JP 2014519534 A5 JP2014519534 A5 JP 2014519534A5 JP 2014509633 A JP2014509633 A JP 2014509633A JP 2014509633 A JP2014509633 A JP 2014509633A JP 2014519534 A5 JP2014519534 A5 JP 2014519534A5
- Authority
- JP
- Japan
- Prior art keywords
- emulsion
- reaction
- stirred
- rpm
- dodecane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000000839 emulsion Substances 0.000 description 39
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920002633 Kraton (polymer) Polymers 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- MHYWMAUCJNDHPY-UHFFFAOYSA-N 2-[n-ethyl-4-[(4-nitrophenyl)diazenyl]anilino]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(N(CCOC(=O)C(C)=C)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 MHYWMAUCJNDHPY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11003774 | 2011-05-09 | ||
| EP11003774.4 | 2011-05-09 | ||
| PCT/EP2012/001898 WO2012152409A1 (en) | 2011-05-09 | 2012-05-03 | Reactive mesogen based polymer particles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014519534A JP2014519534A (ja) | 2014-08-14 |
| JP2014519534A5 true JP2014519534A5 (enExample) | 2016-09-15 |
| JP6182523B2 JP6182523B2 (ja) | 2017-08-16 |
Family
ID=46044635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014509633A Active JP6182523B2 (ja) | 2011-05-09 | 2012-05-03 | 反応性メソゲンに基づくポリマー粒子 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9109160B2 (enExample) |
| EP (1) | EP2707457B1 (enExample) |
| JP (1) | JP6182523B2 (enExample) |
| KR (1) | KR101971300B1 (enExample) |
| CN (1) | CN103547655B (enExample) |
| TW (1) | TWI530551B (enExample) |
| WO (1) | WO2012152409A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016503185A (ja) * | 2012-12-14 | 2016-02-01 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 複屈折ｒｍレンズ |
| KR102205991B1 (ko) * | 2013-04-18 | 2021-01-21 | 메르크 파텐트 게엠베하 | 콜레스테릭 중합체 입자를 포함하는 층 또는 물품 |
| US9796926B2 (en) * | 2014-02-13 | 2017-10-24 | Merck Patent Gmbh | Reactive mesogen based polymer particles |
| KR102023710B1 (ko) * | 2014-02-20 | 2019-09-20 | 동우 화인켐 주식회사 | 염료 및 착색 경화성 수지 조성물 |
| WO2015137816A1 (en) | 2014-03-14 | 2015-09-17 | Dutch Polymer Insitute | Nanoporous adsorbent material for removing species from an aqueous solution |
| CN109423300B (zh) * | 2017-08-23 | 2020-10-30 | 江苏集萃智能液晶科技有限公司 | 单分散聚合物微粒的制备方法 |
| KR102187883B1 (ko) * | 2017-12-13 | 2020-12-11 | (주)태광뉴텍 | 다관능 에폭시 및 아크릴 계열의 코팅 조성물과 이의 제조방법 |
| WO2019141833A1 (en) | 2018-01-22 | 2019-07-25 | Merck Patent Gmbh | Dielectric materials |
| CN110117341B (zh) * | 2018-02-07 | 2020-10-23 | 江苏集萃智能液晶科技有限公司 | 一种多孔的功能化聚合物微球的制备方法 |
| CN110964142B (zh) * | 2018-09-29 | 2020-12-15 | 江苏集萃智能液晶科技有限公司 | 具有多孔结构的手性聚合物微球及其制备方法 |
| EP3867335A1 (en) | 2018-10-18 | 2021-08-25 | Merck Patent GmbH | Dielectric copolymer materials |
| WO2020078938A1 (en) | 2018-10-18 | 2020-04-23 | Merck Patent Gmbh | Dielectric copolymer materials |
| CN112745706B (zh) * | 2020-12-25 | 2022-04-05 | 北京生泰宝科技有限公司 | 一种电致变色涂料及其制备方法、电致变色膜及其制备方法 |
| KR102613630B1 (ko) | 2021-03-11 | 2023-12-15 | 한국과학기술원 | 자극감응성 복합섬유와 이의 제조방법 및 이를 포함하는 광열 엑추에이터 시스템 |
| WO2025061815A1 (en) | 2023-09-22 | 2025-03-27 | Merck Patent Gmbh | Dielectric copolymer materials |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0261712A1 (en) | 1986-09-04 | 1988-03-30 | Koninklijke Philips Electronics N.V. | Picture display cell, method of forming an orientation layer on a substrate of the picture display cell and monomeric compounds for use in the orientation layer |
| JPH04218513A (ja) * | 1990-08-09 | 1992-08-10 | Sagami Chem Res Center | メソゲン基を有する重合性モノマーおよびポリマー |
| EP0591508B2 (en) | 1992-04-27 | 2003-01-15 | MERCK PATENT GmbH | Electrooptical liquid crystal system |
| US5518652A (en) | 1993-07-05 | 1996-05-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline copolymer |
| US5380362A (en) | 1993-07-16 | 1995-01-10 | Copytele, Inc. | Suspension for use in electrophoretic image display systems |
| US5403518A (en) | 1993-12-02 | 1995-04-04 | Copytele, Inc. | Formulations for improved electrophoretic display suspensions and related methods |
| DE4405316A1 (de) | 1994-02-19 | 1995-08-24 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| DE19504224A1 (de) | 1994-02-23 | 1995-08-24 | Merck Patent Gmbh | Flüssigkristallines Material |
| DE4418075C2 (de) * | 1994-05-24 | 2000-06-29 | Daimler Chrysler Ag | Effektlack bzw. Effektlackierung, insbesondere für Fahrzeugkarosserien, unter Verwendung von flüssigkristallinen Interferenzpigmenten |
| CA2208509C (en) * | 1994-12-21 | 2007-05-08 | Raychem Corporation | Method of making liquid crystal composite |
| GB2299333B (en) | 1995-03-29 | 1998-11-25 | Merck Patent Gmbh | Reactive terphenyls |
| US7304634B2 (en) | 1995-07-20 | 2007-12-04 | E Ink Corporation | Rear electrode structures for electrophoretic displays |
| DE19532408A1 (de) | 1995-09-01 | 1997-03-06 | Basf Ag | Polymerisierbare flüssigkristalline Verbindungen |
| GB2306470B (en) | 1995-10-05 | 1999-11-03 | Merck Patent Gmbh | Reactive liquid crystalline compound |
| DE19602795A1 (de) | 1996-01-26 | 1997-07-31 | Basf Ag | Verfahren zur Herstellung von Pigmentpartikeln |
| DE19602848A1 (de) * | 1996-01-26 | 1997-07-31 | Basf Ag | Verfahren zur Herstellung von Pigmenten |
| JPH1062739A (ja) | 1996-08-21 | 1998-03-06 | Fuji Xerox Co Ltd | 可逆表示媒体 |
| US5783614A (en) | 1997-02-21 | 1998-07-21 | Copytele, Inc. | Polymeric-coated dielectric particles and formulation and method for preparing same |
| US5932633A (en) | 1997-08-22 | 1999-08-03 | Copytele, Inc. | Method for making polymers-coated pigment particles using initiator-treated pigments |
| WO1999010769A1 (en) | 1997-08-28 | 1999-03-04 | E-Ink Corporation | Applications for encapsulated electrophoretic displays |
| US7247379B2 (en) | 1997-08-28 | 2007-07-24 | E Ink Corporation | Electrophoretic particles, and processes for the production thereof |
| GB9812636D0 (en) * | 1998-06-11 | 1998-08-12 | Rolic Ag | Optical component orientation layer and layerable polymerisable mixture |
| US7038655B2 (en) | 1999-05-03 | 2006-05-02 | E Ink Corporation | Electrophoretic ink composed of particles with field dependent mobilities |
| US6514578B1 (en) | 1999-06-30 | 2003-02-04 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Polymerizable mesogenic tolanes |
| JP4433526B2 (ja) * | 1999-10-07 | 2010-03-17 | コニカミノルタホールディングス株式会社 | 液晶性高分子水系分散物の製造方法、液晶性高分子水系分散物、光学素子の製造方法及び光学素子 |
| JP2001262144A (ja) | 2000-03-16 | 2001-09-26 | Dainippon Ink & Chem Inc | 液晶干渉性微粒子及びその製造方法 |
| US7236290B1 (en) | 2000-07-25 | 2007-06-26 | E Ink Corporation | Electrophoretic medium with improved stability |
| JP2002201222A (ja) * | 2000-09-19 | 2002-07-19 | Merck Patent Gmbh | ポリマービーズ、ポリマービーズの使用方法、反射フィルム、セキュリティマーク、有価証券、セキュリティ装置 |
| CN1282027C (zh) | 2001-04-02 | 2006-10-25 | 伊英克公司 | 具有改善的图像稳定性的电泳介质 |
| WO2002093246A1 (en) | 2001-05-15 | 2002-11-21 | E Ink Corporation | Electrophoretic particles |
| US6876427B2 (en) | 2001-09-21 | 2005-04-05 | 3M Innovative Properties Company | Cholesteric liquid crystal optical bodies and methods of manufacture and use |
| TWI250894B (en) | 2002-01-03 | 2006-03-11 | Sipix Imaging Inc | Functionalized halogenated polymers for microencapsulation |
| TWI229776B (en) | 2002-01-03 | 2005-03-21 | Sipix Imaging Inc | A novel electrophoretic dispersion with a fluorinated solvent and a charge controlling agent |
| CN1665903A (zh) | 2002-07-06 | 2005-09-07 | 默克专利股份有限公司 | 含非手性液晶材料的薄片 |
| TWI293715B (en) | 2002-10-10 | 2008-02-21 | Sipix Imaging Inc | A method for inducing or enhancing the threshold of an electrophoretic display, an electrophoretic fluid and an electrophoretic display |
| TWI228632B (en) | 2003-02-06 | 2005-03-01 | Sipix Imaging Inc | Improved electrophoretic display with a bi-modal particle system |
| US7390901B2 (en) | 2003-08-08 | 2008-06-24 | Sipix Imaging, Inc. | Fluorinated dyes or colorants and their uses |
| JP4637839B2 (ja) * | 2003-08-08 | 2011-02-23 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 反応性メソゲンを有する、液晶分子を配向させるための配向層 |
| US7277218B2 (en) | 2003-11-04 | 2007-10-02 | Sipix Imaging, Inc. | Electrophoretic compositions |
| DE602005006508D1 (de) * | 2004-12-07 | 2008-06-19 | Merck Patent Gmbh | Polymerisierbare Flüssigkristallzusammensetzungen und Polarisator |
| US7652656B2 (en) | 2006-05-19 | 2010-01-26 | Xerox Corporation | Electrophoretic display and method of displaying images |
| KR20070112943A (ko) | 2006-05-24 | 2007-11-28 | 엘지.필립스 엘시디 주식회사 | 전자잉크 패널과 이를 구비한 전자잉크 표시장치 및 그의구동방법 |
| US20080020007A1 (en) | 2006-07-18 | 2008-01-24 | Zang Hongmei | Liquid-containing film structure |
| WO2008061606A1 (en) * | 2006-11-24 | 2008-05-29 | Merck Patent Gmbh | Cyclohexylene reactive mesogens and their applications |
| EP2240518A2 (en) * | 2008-02-11 | 2010-10-20 | Merck Patent GmbH | Fluid compositions for colour electrophoretic displays |
| US9115464B2 (en) | 2009-02-09 | 2015-08-25 | Merck Patent Gmbh | Particles for electrophoretic displays |
| CN102307914A (zh) | 2009-02-09 | 2012-01-04 | 默克专利有限公司 | 用于电泳显示器的颗粒 |
| US8743451B2 (en) | 2009-02-09 | 2014-06-03 | Merck Patent Gmbh | Coloured particles for electrophoretic displays |
| WO2010089058A1 (en) | 2009-02-09 | 2010-08-12 | Merck Patent Gmbh, | Coloured particles for electrophoretic displays |
| CN103068929A (zh) | 2010-08-07 | 2013-04-24 | 默克专利有限公司 | 用于电泳显示器的粒子 |
-
2012
- 2012-05-03 US US14/116,454 patent/US9109160B2/en active Active
- 2012-05-03 EP EP12719277.1A patent/EP2707457B1/en active Active
- 2012-05-03 CN CN201280022795.5A patent/CN103547655B/zh active Active
- 2012-05-03 JP JP2014509633A patent/JP6182523B2/ja active Active
- 2012-05-03 WO PCT/EP2012/001898 patent/WO2012152409A1/en not_active Ceased
- 2012-05-03 KR KR1020137032154A patent/KR101971300B1/ko not_active Expired - Fee Related
- 2012-05-09 TW TW101116545A patent/TWI530551B/zh not_active IP Right Cessation
-
2015
- 2015-07-23 US US14/807,264 patent/US9598587B2/en not_active Expired - Fee Related
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