JP2007186430A - 新規重合性化合物 - Google Patents
新規重合性化合物 Download PDFInfo
- Publication number
- JP2007186430A JP2007186430A JP2006003724A JP2006003724A JP2007186430A JP 2007186430 A JP2007186430 A JP 2007186430A JP 2006003724 A JP2006003724 A JP 2006003724A JP 2006003724 A JP2006003724 A JP 2006003724A JP 2007186430 A JP2007186430 A JP 2007186430A
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- 0 COC(*(F)=C)=O Chemical compound COC(*(F)=C)=O 0.000 description 1
- QIGGVLCSBKJPIG-UHFFFAOYSA-N Cc(cc(cc1)O)c1OC(c(cc1)cc(cc2)c1cc2OC)=O Chemical compound Cc(cc(cc1)O)c1OC(c(cc1)cc(cc2)c1cc2OC)=O QIGGVLCSBKJPIG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3861—Poly(meth)acrylate derivatives containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
また、重合性基とともに、反応性の官能基を有した化合物は、各種機能性の化合物と反応させることが容易であるため、各種機能性材料のモノマーや中間体として必要とされている。
すなわち本発明は、下記一般式(I)で表される新規重合性化合物を提供するものである。
一般式(I)の化合物の原料として、下記一般式(II)及び(III)で表される化合物が挙げられる。
一般式(III)中、Bは、フェノール性水酸基の保護基を表す。フェノール性水酸基の保護基としては、通常使用されるものでよく、例としては、ベンジル基、p−メトキシベンジル(MPM)基、トリメチルシリル(TMS)基、t−ブチルジメチルシリル(TBDMS)基、メトキシメチル(MOM)基、メトキシエトキシメチル(MEM)基等が挙げられ、特にベンジル基が好ましい。
以下の実施例(合成例)において、化合物の構造は、核磁気共鳴(1H−NMR)スペクトル、赤外吸収(IR)スペクトル等で確認した。
また、重合性液晶化合物の熱転移挙動は、DSC及び偏光顕微鏡を用いて観察し、Cは結晶を、Nはネマチック相を、Iは等方性液体相をそれぞれ表す。
本発明の化合物No.2を以下のステップ1〜2の手順に従って合成した。
<ステップ1>
下記反応式に従い、ベンジルエーテル化合物を以下のように合成した。
ステップ1で得られたベンジルエーテル化合物を用いて、下記反応式に従い以下のようにして化合物No.2を合成した。
得られた白色個体について分析を行ったところ、該白色固体は目的物である化合物No.2であることが確認された。分析結果を下記に示す。
(1)IR〔KBr錠剤法〕(cm-1)
3379,2954,2927,2870,1724,1628,1601,1501,1474,1450,1400,1373,1339,1277,1172,1142,1111,1057
(2)1H−NMR〔CDCl3〕(ppm)
0.9(t;3H),1.5−1.8(m;2H),2.4−2.6(t;2H),4.9(s;1H),6.0−7.4(m;7H),7.7−8.3(m;4H),8.8(s;1H)
(3)融点
149.3℃(DSC,5℃/min)
実施例1で得られた化合物No.2を中間体原料として、下記、反応式に従い、重合性液晶化合物−1を合成した。
(1)IR(cm-1)
2936,2866,1624,1474,1404,1339,1273,1246,1200,1169,1150,1065,1022
(2)1H−NMR(ppm)
0.9(t;3H),1.5−1.9(m;10H),2.6(q;2H),3.9−4.3(m;4H),5.7−6.6(m;6H),7.1−7.5(m;6H),7.7−8.3(m;7H),8.7(s;1H),8.9(s;1H)
(3)熱転移挙動
下記〔化32〕に、熱転移挙動を示す。
Claims (2)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006003724A JP4545095B2 (ja) | 2006-01-11 | 2006-01-11 | 新規重合性化合物 |
US12/096,762 US7754912B2 (en) | 2006-01-11 | 2006-11-14 | Polymerizable compounds |
CN2006800458352A CN101326152B (zh) | 2006-01-11 | 2006-11-14 | 新型聚合性化合物 |
KR1020087012899A KR101337887B1 (ko) | 2006-01-11 | 2006-11-14 | 신규 중합성 화합물 |
PCT/JP2006/322597 WO2007080702A1 (ja) | 2006-01-11 | 2006-11-14 | 新規重合性化合物 |
EP06823371A EP1972612A4 (en) | 2006-01-11 | 2006-11-14 | NEW POLYMERIZABLE COMPOUNDS |
TW095143051A TWI395732B (zh) | 2006-01-11 | 2006-11-21 | Novel polymerizable compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006003724A JP4545095B2 (ja) | 2006-01-11 | 2006-01-11 | 新規重合性化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007186430A true JP2007186430A (ja) | 2007-07-26 |
JP4545095B2 JP4545095B2 (ja) | 2010-09-15 |
Family
ID=38256115
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006003724A Expired - Fee Related JP4545095B2 (ja) | 2006-01-11 | 2006-01-11 | 新規重合性化合物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7754912B2 (ja) |
EP (1) | EP1972612A4 (ja) |
JP (1) | JP4545095B2 (ja) |
KR (1) | KR101337887B1 (ja) |
CN (1) | CN101326152B (ja) |
TW (1) | TWI395732B (ja) |
WO (1) | WO2007080702A1 (ja) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008179654A (ja) * | 2006-12-29 | 2008-08-07 | Adeka Corp | 重合性化合物及び重合性組成物 |
WO2008120424A1 (ja) * | 2007-03-29 | 2008-10-09 | Adeka Corporation | 重合性化合物及び重合性組成物 |
JP2009035675A (ja) * | 2007-08-03 | 2009-02-19 | Mitsubishi Rayon Co Ltd | 重合体および該重合体を含有するレジスト組成物 |
US8895151B2 (en) | 2010-03-09 | 2014-11-25 | Zeon Corporation | Heat insulating member, heat insulating laminated glass, and heat insulating laminated glass article |
WO2015064581A1 (ja) | 2013-10-28 | 2015-05-07 | 日本ゼオン株式会社 | 複層フィルム、光学異方性積層体、円偏光板、有機エレクトロルミネッセンス表示装置、及び製造方法 |
JP2015522085A (ja) * | 2012-06-28 | 2015-08-03 | エルジー・ケム・リミテッド | 重合性液晶化合物、これを含む液晶組成物及び光学異方体 |
US9200201B2 (en) | 2009-10-22 | 2015-12-01 | Zeon Corporation | Heat-insulating particulate pigment and infrared-reflective coating solution |
JPWO2015098702A1 (ja) * | 2013-12-25 | 2017-03-23 | Dic株式会社 | メソゲン基を含有する化合物、それを用いた混合物、組成物、及び、光学異方体 |
WO2019026889A1 (ja) * | 2017-08-01 | 2019-02-07 | 大阪ガスケミカル株式会社 | 単官能性(メタ)アクリレート及び硬化性組成物 |
US10207474B2 (en) | 2015-01-28 | 2019-02-19 | Zeon Corporation | Multilayer film, optically anisotropic layered body, circularly polarizing plate, organic electroluminescence display device, and manufacturing method |
US10386679B2 (en) | 2015-04-21 | 2019-08-20 | Zeon Corporation | Multilayer film and method for manufacturing same, method for manufacturing optically anisotropic transfer body, optically anisotropic layer, optically anisotropic member, and optical layered body |
US10705385B2 (en) | 2016-11-30 | 2020-07-07 | Zeon Corporation | Optical laminate, circularly polarizing plate, touch panel, and image display device |
US10712484B2 (en) | 2015-01-30 | 2020-07-14 | Zeon Corporation | Multilayer film, use thereof, and production method thereof |
WO2020196306A1 (ja) | 2019-03-28 | 2020-10-01 | 東洋紡株式会社 | 反射防止用円偏光板およびそれを用いた画像表示装置 |
WO2020241313A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ |
WO2021079815A1 (ja) | 2019-10-23 | 2021-04-29 | 日本ゼオン株式会社 | 液晶硬化層転写シール、液晶硬化層転写物、及び液晶硬化層転写シールの真正性判定方法 |
US11067731B2 (en) | 2015-02-26 | 2021-07-20 | Zeon Corporation | Transfer body for optical film, optical film, organic electroluminescent display device, and method for manufacturing optical film |
US11899167B2 (en) | 2019-05-28 | 2024-02-13 | Toyobo Co., Ltd. | Polyester film, laminated film, and use thereof |
US11926720B2 (en) | 2019-05-28 | 2024-03-12 | Toyobo Co., Ltd. | Polyester film and application therefor |
US11934226B2 (en) | 2019-02-08 | 2024-03-19 | Toyobo Co., Ltd. | Foldable display and portable terminal device |
US11939499B2 (en) | 2019-05-28 | 2024-03-26 | Toyobo Co., Ltd. | Multilayer film and use of same |
US11997916B2 (en) | 2019-02-08 | 2024-05-28 | Toyobo Co., Ltd. | Polyester film and use thereof |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
US7910019B2 (en) | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
US8628685B2 (en) * | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
US8613868B2 (en) * | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
JP5642678B2 (ja) * | 2008-08-22 | 2014-12-17 | デューク ユニバーシティーDuke University | 面及び導波路のためのメタ材料 |
JP6055569B1 (ja) * | 2016-05-18 | 2016-12-27 | 日本ゼオン株式会社 | 重合性化合物、混合物、重合性液晶組成物、高分子、光学フィルム、光学異方体、偏光板、フラットパネル表示装置、有機エレクトロルミネッセンス表示装置および反射防止フィルム |
JP2018070546A (ja) * | 2016-11-02 | 2018-05-10 | Dic株式会社 | エステル結合を有するビスフェノール誘導体 |
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-
2006
- 2006-01-11 JP JP2006003724A patent/JP4545095B2/ja not_active Expired - Fee Related
- 2006-11-14 EP EP06823371A patent/EP1972612A4/en not_active Withdrawn
- 2006-11-14 KR KR1020087012899A patent/KR101337887B1/ko active IP Right Grant
- 2006-11-14 US US12/096,762 patent/US7754912B2/en not_active Expired - Fee Related
- 2006-11-14 WO PCT/JP2006/322597 patent/WO2007080702A1/ja active Application Filing
- 2006-11-14 CN CN2006800458352A patent/CN101326152B/zh not_active Expired - Fee Related
- 2006-11-21 TW TW095143051A patent/TWI395732B/zh not_active IP Right Cessation
Patent Citations (3)
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JP2004277488A (ja) * | 2003-03-13 | 2004-10-07 | Dainippon Ink & Chem Inc | 重合性液晶組成物及び光学異方体 |
JP2005208416A (ja) * | 2004-01-23 | 2005-08-04 | Nitto Denko Corp | 逆波長分散位相差フィルム、それを用いた偏光板及びディスプレイ装置 |
WO2006049111A1 (ja) * | 2004-11-04 | 2006-05-11 | Adeka Corporation | 重合性化合物及び該重合性化合物を含有する組成物 |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008179654A (ja) * | 2006-12-29 | 2008-08-07 | Adeka Corp | 重合性化合物及び重合性組成物 |
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EP1972612A1 (en) | 2008-09-24 |
EP1972612A4 (en) | 2010-04-14 |
JP4545095B2 (ja) | 2010-09-15 |
US20090247782A1 (en) | 2009-10-01 |
TW200730492A (en) | 2007-08-16 |
US7754912B2 (en) | 2010-07-13 |
WO2007080702A1 (ja) | 2007-07-19 |
TWI395732B (zh) | 2013-05-11 |
CN101326152B (zh) | 2012-10-17 |
KR20080084929A (ko) | 2008-09-22 |
KR101337887B1 (ko) | 2013-12-09 |
CN101326152A (zh) | 2008-12-17 |
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