WO2007120458A1 - Liquid crystal compositions, polymer networks derived therefrom and process for making the same - Google Patents

Liquid crystal compositions, polymer networks derived therefrom and process for making the same Download PDF

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Publication number
WO2007120458A1
WO2007120458A1 PCT/US2007/008079 US2007008079W WO2007120458A1 WO 2007120458 A1 WO2007120458 A1 WO 2007120458A1 US 2007008079 W US2007008079 W US 2007008079W WO 2007120458 A1 WO2007120458 A1 WO 2007120458A1
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Prior art keywords
group
compound
liquid crystal
formula
meth
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PCT/US2007/008079
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English (en)
French (fr)
Inventor
Marc Goldfinger
Jose Manuel Rodriguez-Parada
Lee Silverman
Original Assignee
E. I. Du Pont De Nemours And Company
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Filing date
Publication date
Application filed by E. I. Du Pont De Nemours And Company filed Critical E. I. Du Pont De Nemours And Company
Priority to DE602007013541T priority Critical patent/DE602007013541D1/de
Priority to JP2009503059A priority patent/JP2009532362A/ja
Priority to EP07754581A priority patent/EP2001974B1/en
Publication of WO2007120458A1 publication Critical patent/WO2007120458A1/en

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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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    • 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
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
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    • 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
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    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
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    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
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    • 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

Definitions

  • nematic phase is one wherein a chiral moiety is present, referred to as a twisted nematic or cholesteric phase.
  • the molecules are parallel to each other as in the nematic phase, but the director of molecules (the average direction of the rodlike molecules) changes direction through the thickness of a layer to provide a helical packing of the nematic molecules.
  • the pitch of the helix is perpendicular to the long axes of the molecules.
  • X is Cl, Br or -OH; X 1 is selected from the group: Cl, Br, I, -OMs, -OTs and -OTf (as described below); and n is an integer equal to 3 to 20; and a first reaction solvent at a first reaction temperature to provide one or more polyf ⁇ inctionalized aryl alkanoate ester(s) and a first spent reaction mixture; and (c) reacting the one or more polyfunctionalized aryl alkanoate ester(s) with a (meth)acrylate salt in the presence of a phase transfer catalyst, and a second reaction solvent at a second reaction temperature; to provide one or more poly (meth)acrylate-aryl alkanoate ester(s) and a second spent reaction mixture.
  • R 3 - R 11 are as described above.
  • This embodiment of the process can be used to provide compounds of Formula (IIIa-e) described above.
  • Specific ester diols of Formula (VIIa-g) useful and preferred in the process include: 4- hydroxyphenyl 4-hydroxybenzoate, 2-methyl-4-hydroxyphenyl 4- hydroxybenzoate, 3-methyl-4-hydroxyphenyl 4-hydroxybenzoate, 2-chloro-4- hydroxyphenyl 4-hydroxybenzoate,
  • ester diols useful and preferred in the process that provide specific compounds as described by Formula (VIIe) derived from 6-hydroxy-2-napthalene carboxylic acid are: 6-hydroxynapthalene-2-carboxylic acid 4-hydroxyphenyl ester (CAS No. [17295-17-9]), ⁇ -hydroxynapthalene ⁇ -carboxylic acid 2-methyl- 4-hydroxyphenyl ester, 6-hydroxynapthalene-2-carboxylic acid 3-methyl-4- hydroxyphenyl ester, 6-hydroxynapthalene-2 -carboxylic acid 2-chloro-4- hydroxyphenyl ester, and 6-hydroxynapthalene-2-carboxylic acid 3-chloro-4- hydroxyphenyl ester.
  • the base also can be an amine base, and particularly a hindered amine base such as a tertiary aliphatic, aromatic or heterocyclic amine as described above; to provide an ammonium (meth)acrylate salt.
  • Preferred (meth)acrylate salts for step (c) are selected from the group: potassium (meth)acrylate and ammonium (meth)acrylates selected from the group: triethylammonium.
  • the (meth)acrylate salt is provided by mixing (meth)acrylic acid and an alkali metal carbonate selected from the group: potassium hydrogen carbonate and potassium carbonate, in a molar ratio of about 1 : 1 to about 1 : 5, respectively, in said second reaction solvent.
  • phase transfer catalyst in which the total number of carbon atoms attached to each nitrogen or phosphorus atom is at least 4. It is especially preferred that the number should be in the range of from 16 to 40.
  • Other substances suitable for use herein as the phase transfer catalyst include those reviewed by E. V. Dehmlow in Angewante Chemie, (International Edition), 13_, 170 (1974).
  • amine bases selected from the group: triethylamine, diisopropylethylamine, tributyl amine, pyridine, and 2,6- dimethylpyridine.
  • the base is preferably present in an amount of about 0.8 to about 5 equivalents per equivalent of the functionalized alkyl acid halide(s).
  • the compounds provided by this invention generally have important attributes that are different from conventional polymerizable liquid crystal bis (meth)acrylates.
  • a process to produce a multilayer laminate provides a polymeric sheet laminated to a polymeric film that is coated with the twisted nematic liquid crystal layer.
  • the polymeric sheet may be lightly bonded to the film with the twisted nematic liquid crystal through a nip roll bonding process.
  • the components may be heated to a temperature sufficient to promote temporary fusion bonding, i.e., to cause the surfaces of the polymeric sheet or the polymeric film to become tacky. Suitable temperatures are within the range of about 50 0 C to about 120 0 C, with the preferred surface temperatures reaching about 65°C.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal Substances (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/US2007/008079 2006-03-31 2007-04-02 Liquid crystal compositions, polymer networks derived therefrom and process for making the same WO2007120458A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE602007013541T DE602007013541D1 (de) 2006-03-31 2007-04-02 Flüssigkristallzusammensetzungen, polymernetze daraus und herstellungsverfahren dafür
JP2009503059A JP2009532362A (ja) 2006-03-31 2007-04-02 液晶組成物、それから誘導されるポリマー網状構造およびその製造方法
EP07754581A EP2001974B1 (en) 2006-03-31 2007-04-02 Liquid crystal compositions, polymer networks derived therefrom and process for making the same

Applications Claiming Priority (2)

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US78852506P 2006-03-31 2006-03-31
US60/788,525 2006-03-31

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WO2007120458A1 true WO2007120458A1 (en) 2007-10-25

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US (2) US7879256B2 (US20040106767A1-20040603-C00005.png)
EP (1) EP2001974B1 (US20040106767A1-20040603-C00005.png)
JP (1) JP2009532362A (US20040106767A1-20040603-C00005.png)
KR (1) KR20080109054A (US20040106767A1-20040603-C00005.png)
CN (1) CN101415797A (US20040106767A1-20040603-C00005.png)
DE (1) DE602007013541D1 (US20040106767A1-20040603-C00005.png)
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Cited By (6)

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WO2008081631A1 (ja) 2006-12-29 2008-07-10 Adeka Corporation 重合性化合物及び重合性組成物
WO2009023762A1 (en) * 2007-08-15 2009-02-19 E. I. Du Pont De Nemours And Company Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom
WO2009122868A1 (ja) * 2008-04-01 2009-10-08 株式会社Adeka 三官能（メタ）アクリレート化合物及び該化合物を含有する重合性組成物
WO2010144411A1 (en) * 2009-06-08 2010-12-16 E. I. Du Pont De Nemours And Company Liquid crystal compositions
WO2011078099A1 (ja) * 2009-12-25 2011-06-30 住友化学株式会社 ジエポキシ化合物、その製造方法および該ジエポキシ化合物を含む組成物
CN107083242A (zh) * 2017-04-21 2017-08-22 深圳市屏柔科技有限公司 一种液晶浆料及其配制方法

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US7744970B2 (en) * 2005-05-26 2010-06-29 E. I. Du Pont De Nemours And Company Multilayer laminates comprising twisted nematic liquid crystals
US7749577B2 (en) * 2005-05-26 2010-07-06 E.I. Du Pont De Nemours And Company High strength multilayer laminates comprising twisted nematic liquid crystals
EP1973987A1 (en) 2005-12-29 2008-10-01 E.I. Du Pont De Nemours And Company Composition for reducing the transmission of infrared radiation
US7879256B2 (en) * 2006-03-31 2011-02-01 E. I. Du Pont De Nemours And Company Liquid crystal compositions, polymer networks derived therefrom and process for making the same
US7914700B2 (en) 2006-03-31 2011-03-29 E. I. Du Pont De Nemours And Company Liquid crystal compositions and polymer networks derived therefrom
EP2176268A2 (en) * 2007-08-15 2010-04-21 E. I. du Pont de Nemours and Company Chiral compounds, liquid crystal compositions and polymer networks derived therefrom
WO2009134822A2 (en) * 2008-05-01 2009-11-05 The Government Of The United States Of America, As Represented By The Secretary Of The Navy Fluorescent organic nanoparticles
EP2113550B1 (en) 2008-05-02 2011-10-12 Sony Corporation A composition comprising at least one type of liquid crystal
US20090324799A1 (en) * 2008-05-15 2009-12-31 Robert Michael Hartman Maximizing utilization of municipal sewage treatment effluents to produce a biofuel, fertilizer and/or animal feed for environmentally sustainable minded communities
KR101770833B1 (ko) * 2008-08-29 2017-08-24 메르크 파텐트 게엠베하 액정 매질 및 액정 디스플레이
US7988881B2 (en) * 2008-09-30 2011-08-02 E. I. Du Pont De Nemours And Company Multilayer laminates comprising chiral nematic liquid crystals
US20100308268A1 (en) * 2009-06-08 2010-12-09 E. I. Du Pont De Nemours And Company Liquid crystal compositions
US8044228B2 (en) 2009-06-08 2011-10-25 E.I. Du Pont De Nemours And Company Liquid crystal compositions
US8067068B2 (en) * 2009-06-08 2011-11-29 E.I. Du Pont De Nemours And Company Liquid crystal compositions
US20120071618A1 (en) * 2009-06-08 2012-03-22 E.I. Du Pont De Nemours And Company Liquid crystal compositions
EP2513249B1 (de) * 2009-12-17 2013-10-02 Basf Se Flüssigkristalline mischungen
TWI482839B (zh) * 2010-01-26 2015-05-01 Jnc Corp 液晶組成物及液晶顯示元件
WO2012074081A1 (en) * 2010-11-30 2012-06-07 Semiconductor Energy Laboratory Co., Ltd. Liquid crystal composition, polymer/liquid crystal composite, liquid crystal element, and liquid crystal display device
SG190966A1 (en) * 2010-12-07 2013-07-31 Sicpa Holding Sa Simplified control of color shifting properties of a chiral liquid crystal polymer
WO2012076534A1 (en) * 2010-12-07 2012-06-14 Sicpa Holding Sa Composite marking based on chiral liquid crystal precursors
EP2665730B1 (en) * 2011-01-21 2019-07-24 The Provost, Fellows, Foundation Scholars, & the other members of Board, of the College of the Holy & Undiv. Trinity of Queen Elizabeth near Dublin Compounds with super-aspirin effects
KR20130047588A (ko) * 2011-10-31 2013-05-08 가부시키가이샤 한도오따이 에네루기 켄큐쇼 액정 조성물, 고분자/액정 복합체, 액정 소자, 및 액정 표시 장치
CN103013534B (zh) * 2012-11-30 2014-09-24 京东方科技集团股份有限公司 聚合物分散液晶及其制备方法和应用
JP6155520B2 (ja) * 2013-10-01 2017-07-05 エルジー・ケム・リミテッド 液晶組成物
CN104570463B (zh) * 2015-01-22 2017-12-08 京东方科技集团股份有限公司 带镜子功能的显示装置及其制造方法
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
JP2021152147A (ja) * 2020-03-23 2021-09-30 住友化学株式会社 重合性液晶化合物、重合性液晶組成物、位相差フィルム、楕円偏光板および有機ｅｌ表示装置
CN113620805B (zh) * 2021-07-23 2024-05-24 江苏创拓新材料有限公司 可聚合化合物、组合物及光学各向异性体

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