WO2009023762A1 - Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom - Google Patents

Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom Download PDF

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Publication number
WO2009023762A1
WO2009023762A1 PCT/US2008/073121 US2008073121W WO2009023762A1 WO 2009023762 A1 WO2009023762 A1 WO 2009023762A1 US 2008073121 W US2008073121 W US 2008073121W WO 2009023762 A1 WO2009023762 A1 WO 2009023762A1
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WO
WIPO (PCT)
Prior art keywords
compound
group
formula
liquid crystal
mixture
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.)
Ceased
Application number
PCT/US2008/073121
Other languages
English (en)
French (fr)
Inventor
Marc B. Goldfinger
Kai Qi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP08827491A priority Critical patent/EP2179007B1/en
Priority to US12/672,739 priority patent/US8137582B2/en
Priority to JP2010521173A priority patent/JP2010536783A/ja
Publication of WO2009023762A1 publication Critical patent/WO2009023762A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3488—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines
    • 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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • 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
    • C09K19/52—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
    • 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
    • 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
    • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
    • C09K2219/03—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used in the form of films, e.g. films after polymerisation of LC precursor

Definitions

  • a twisted nematic phase which is also referred to herein as a cholesteric phase or a chiral nematic phase, to selectively reflect light in the infrared, visible or ultraviolet region is useful in many applications.
  • substantially all the light at some wavelengths be reflected.
  • One method for reflecting substantially all of the light in the vicinity of ⁇ o is to use two twisted nematic layers with similar ⁇ 0 , one right-handed and one left-handed. Light in the region around ⁇ 0 transmitted by the first layer will be reflected by the second layer, with the result that substantially all of the incident light with a wavelength in the vicinity of ⁇ o will be reflected.
  • polymerizable monomers useful in liquid crystal compositions are disclosed in US 5833880, DE 4408170, EP 261712, EP 331233 Bl, EP 397263 Bl, and WO1998047979, each of which is incorporated as a part hereof by reference.
  • a preferred group of polymerizable monomers for the polymerizable liquid crystal compositions of the invention are those of formula (VII):
  • thermal transitions are given in degrees Centigrade.
  • K crystal
  • N nematic
  • S smectic
  • TN* twisted nematic
  • X unidentified phase
  • I isotropic
  • P polymerized.
  • the thermal transitions and phase assignments were made with differential scanning calorimetry and hotstage optical microscopy. The following abbreviations are used in the examples:
  • DI water deionized water

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal Substances (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/US2008/073121 2007-08-15 2008-08-14 Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom Ceased WO2009023762A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP08827491A EP2179007B1 (en) 2007-08-15 2008-08-14 Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom
US12/672,739 US8137582B2 (en) 2007-08-15 2008-08-14 Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom
JP2010521173A JP2010536783A (ja) 2007-08-15 2008-08-14 アルカロイドモノマー、液晶組成物およびそれらから誘導されるポリマー網状構造

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95594907P 2007-08-15 2007-08-15
US60/955,949 2007-08-15

Publications (1)

Publication Number Publication Date
WO2009023762A1 true WO2009023762A1 (en) 2009-02-19

Family

ID=39811438

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/073121 Ceased WO2009023762A1 (en) 2007-08-15 2008-08-14 Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom

Country Status (6)

Country Link
US (1) US8137582B2 (https=)
EP (1) EP2179007B1 (https=)
JP (1) JP2010536783A (https=)
KR (1) KR20100066510A (https=)
TW (1) TW200923050A (https=)
WO (1) WO2009023762A1 (https=)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7736532B2 (en) 2005-12-29 2010-06-15 E.I. Du Pont De Nemours And Company Composition for reducing the transmission of infrared radiation
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
WO2010144411A1 (en) 2009-06-08 2010-12-16 E. I. Du Pont De Nemours And Company Liquid crystal compositions
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
US7988881B2 (en) 2008-09-30 2011-08-02 E. I. Du Pont De Nemours And Company Multilayer laminates comprising chiral nematic liquid crystals
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
CN105348428A (zh) * 2015-10-20 2016-02-24 华东师范大学 一种交联型聚合催化剂的制备方法及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637896A (en) * 1982-12-15 1987-01-20 Armstrong World Industries, Inc. Polymeric liquid crystals
WO1995024455A1 (de) * 1994-03-11 1995-09-14 Basf Aktiengesellschaft Neue polymerisierbare flüssigkristalline verbindungen
US6723395B2 (en) * 2001-07-02 2004-04-20 Merck Patent Gmbh Chiral compounds
US7022259B2 (en) * 2002-12-26 2006-04-04 Industrial Technology Research Institute Liquid crystal compounds, preparation thereof, and composition containing the same
US7098359B2 (en) * 2001-07-09 2006-08-29 Southwest Research Institute Mesogens and methods for their synthesis and use
WO2007120458A1 (en) * 2006-03-31 2007-10-25 E. I. Du Pont De Nemours And Company Liquid crystal compositions, polymer networks derived therefrom and process for making the same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US583380A (en) * 1897-05-25 Car-coupling
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
NL8802832A (nl) 1988-02-29 1989-09-18 Philips Nv Methode voor het vervaardigen van een gelaagd element en het aldus verkregen element.
NL8901167A (nl) 1989-05-10 1990-12-03 Philips Nv Methode voor de vervaardiging van een polarisatiefilter, een aldus verkregen polarisatiefilter en een display dat voorzien is van het polarisatiefilter.
DE4408171A1 (de) 1994-03-11 1995-09-14 Basf Ag Neue polymerisierbare flüssigkristalline Verbindungen
EP0794991B1 (en) * 1994-12-03 2000-11-08 MERCK PATENT GmbH Cholesteric polymer network
DE19716822A1 (de) 1997-04-22 1998-10-29 Basf Ag Verfahren zur Herstellung polymerisierbarer flüssigkristalliner Verbindungen
DE59807086D1 (de) 1997-09-02 2003-03-06 Basf Ag Cholesterische effektschichten und verfahren zu deren herstellung
GB9806199D0 (en) * 1998-03-24 1998-05-20 Johnson Matthey Plc Catalytic generation of hydrogen
TWI225090B (en) 2003-08-01 2004-12-11 Ind Tech Res Inst Polymerizable additives having high helical twisting power for liquid crystal compounds, method for preparing the same, and liquid crystal composition containing the additives
US7988881B2 (en) * 2008-09-30 2011-08-02 E. I. Du Pont De Nemours And Company Multilayer laminates comprising chiral nematic liquid crystals

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637896A (en) * 1982-12-15 1987-01-20 Armstrong World Industries, Inc. Polymeric liquid crystals
WO1995024455A1 (de) * 1994-03-11 1995-09-14 Basf Aktiengesellschaft Neue polymerisierbare flüssigkristalline verbindungen
US6723395B2 (en) * 2001-07-02 2004-04-20 Merck Patent Gmbh Chiral compounds
US7098359B2 (en) * 2001-07-09 2006-08-29 Southwest Research Institute Mesogens and methods for their synthesis and use
US7022259B2 (en) * 2002-12-26 2006-04-04 Industrial Technology Research Institute Liquid crystal compounds, preparation thereof, and composition containing the same
WO2007120458A1 (en) * 2006-03-31 2007-10-25 E. I. Du Pont De Nemours And Company Liquid crystal compositions, polymer networks derived therefrom and process for making the same

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US7736532B2 (en) 2005-12-29 2010-06-15 E.I. Du Pont De Nemours And Company Composition for reducing the transmission of infrared radiation
US8334393B2 (en) 2006-03-31 2012-12-18 E I Du Pont De Nemours And Company Chiral compounds and liquid crystal compositions and polymer networks derived therefrom
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
US8344175B2 (en) 2006-03-31 2013-01-01 E I Du Pont De Nemours And Company Liquid crystal compositions, polymer networks derived therefrom and process for making the same
US7988881B2 (en) 2008-09-30 2011-08-02 E. I. Du Pont De Nemours And Company Multilayer laminates comprising chiral nematic liquid crystals
WO2010144411A1 (en) 2009-06-08 2010-12-16 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
US8044228B2 (en) 2009-06-08 2011-10-25 E.I. Du Pont De Nemours And Company Liquid crystal compositions
US8034255B2 (en) 2009-06-08 2011-10-11 E. I. Du Pont De Nemours And Company Liquid crystal compositions
CN105348428A (zh) * 2015-10-20 2016-02-24 华东师范大学 一种交联型聚合催化剂的制备方法及其应用

Also Published As

Publication number Publication date
KR20100066510A (ko) 2010-06-17
EP2179007B1 (en) 2012-10-17
JP2010536783A (ja) 2010-12-02
US20110193019A1 (en) 2011-08-11
EP2179007A1 (en) 2010-04-28
US8137582B2 (en) 2012-03-20
TW200923050A (en) 2009-06-01

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