WO2003006570B1 - Novel mesogens and methods for their synthesis and use - Google Patents

Novel mesogens and methods for their synthesis and use

Info

Publication number
WO2003006570B1
WO2003006570B1 PCT/US2002/021427 US0221427W WO03006570B1 WO 2003006570 B1 WO2003006570 B1 WO 2003006570B1 US 0221427 W US0221427 W US 0221427W WO 03006570 B1 WO03006570 B1 WO 03006570B1
Authority
WO
WIPO (PCT)
Prior art keywords
group
groups
independently
substituted
atoms
Prior art date
Application number
PCT/US2002/021427
Other languages
French (fr)
Other versions
WO2003006570A3 (en
WO2003006570A2 (en
Inventor
Stephen T Wellinghoff
Douglas P Hanson
Original Assignee
Southwest Res Inst
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 Southwest Res Inst filed Critical Southwest Res Inst
Priority to CA2453414A priority Critical patent/CA2453414C/en
Priority to DE60228846T priority patent/DE60228846D1/en
Priority to JP2003512329A priority patent/JP4223394B2/en
Priority to AU2002320317A priority patent/AU2002320317A1/en
Priority to EP02749829A priority patent/EP1412447B1/en
Publication of WO2003006570A2 publication Critical patent/WO2003006570A2/en
Publication of WO2003006570A3 publication Critical patent/WO2003006570A3/en
Publication of WO2003006570B1 publication Critical patent/WO2003006570B1/en

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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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • 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
    • C07C69/90—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 and carboxyl groups
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • 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
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
    • 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
    • C09K19/38—Polymers
    • C09K19/3804—Polymers with mesogenic groups in the main chain
    • C09K19/3809—Polyesters; Polyester derivatives, e.g. polyamides
    • 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

Abstract

New, efficient methods for making novel platform molecules and polymerizable mesogens are provided, as well as the novel mesogens and methods of using same.

Claims

73
AMENDED CLAIMS
[received by the International Bureau on 10 April 2003 (10.04.2003); original claim 9 amended; claims 55-56 added (3 pages)]
Figure imgf000002_0001
wherein X and Y are the same or different terminal functionalities; 2 is a bulky organic group;
R1 and R3 are selected from groups less bulky than R2; and independently substituting a polymerizable group for at least one member selected from the group consisting of X and Y, thereby producing a blend of randomly substituted mesogens. 9. The method of any of claims 1-7 wherein the polymerizable mesogens have the following general structure;
Figure imgf000002_0002
wherein: n is from 1 to 5;
R2 comprises a bulky organic group;
R10 independently is selected from the group consisting of hydrogen and methyl groups;
R14 independently is selected from the group consisting of substituted and unsubstituted alkyl groups having from about 2 to about 6 carbon atoms, provided that the substituted alkyl groups consist essentially of one or 74
substituted groups comprising one or more halogen atom selected from the group consisting of chlorine atoms, bromine atoms, and iodine atoms; and,
D is selected from the group consisting of alkoxy groups and alkoxoyl groups comprising alkyl groups having from about 2 to about 12 carbon atoms, and halogen atoms selected from the group consisting of chlorine atoms, bromine atoms, and iodine atoms. 55. The method of any of claims 1-7 wherein the polymerizable mesogens have the following general structure:
Figure imgf000003_0001
wherein: n is from 1 to 2,
R2 comprises a bulky organic group;
R10 independently is selected from the group consisting of hydrogen and methyl groups; R independently is selected from the group consisting of substituted and unsubstituted alkyl groups having from about 2 to about 6 carbon atoms, provided that the substituted alkyl groups consist essentially of one or fewer methyl substituents; R13 independently is selected from the group consisting of alkylene groups having from about 2 to about 12 carbon atoms. 75
56. The method of any of claims 1-7 wherein the polymerizable mesogens have the following general structure:
Figure imgf000004_0001
wherein: n is from 2 to 5,
R2 comprises a bulky organic group;
Rt0 Independently is selected from the group consisting of hydrogen and methyl groups; R14 independently is selected from the group consisting of substituted and unsubstituted alkyl groups having from about 2 to about 6 carbon atoms, provided that the substituted alkyl groups consist essentially of one or fewer methyl substituents; R13 independently is selected from the group consisting of alkylene groups having from about 2 to about 12 carbon atoms.
PCT/US2002/021427 2001-07-09 2002-07-05 Novel mesogens and methods for their synthesis and use WO2003006570A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA2453414A CA2453414C (en) 2001-07-09 2002-07-05 Mesogens and methods for their synthesis and use
DE60228846T DE60228846D1 (en) 2001-07-09 2002-07-05 NEW MESOGENES, METHOD FOR THEIR PRODUCTION AND USE
JP2003512329A JP4223394B2 (en) 2001-07-09 2002-07-05 Novel mesogens and their synthesis and use
AU2002320317A AU2002320317A1 (en) 2001-07-09 2002-07-05 Novel mesogens and methods for their synthesis and use
EP02749829A EP1412447B1 (en) 2001-07-09 2002-07-05 Novel mesogens and methods for their synthesis and use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30398601P 2001-07-09 2001-07-09
US60/303,986 2001-07-09

Publications (3)

Publication Number Publication Date
WO2003006570A2 WO2003006570A2 (en) 2003-01-23
WO2003006570A3 WO2003006570A3 (en) 2003-09-25
WO2003006570B1 true WO2003006570B1 (en) 2003-11-20

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Country Status (8)

Country Link
US (2) US7098359B2 (en)
EP (1) EP1412447B1 (en)
JP (1) JP4223394B2 (en)
AT (1) ATE407987T1 (en)
AU (1) AU2002320317A1 (en)
CA (1) CA2453414C (en)
DE (1) DE60228846D1 (en)
WO (1) WO2003006570A2 (en)

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US20030168633A1 (en) 2003-09-11
US20050189516A1 (en) 2005-09-01
ATE407987T1 (en) 2008-09-15
WO2003006570A3 (en) 2003-09-25
AU2002320317A1 (en) 2003-01-29
US7098359B2 (en) 2006-08-29
JP2004534901A (en) 2004-11-18
EP1412447B1 (en) 2008-09-10
CA2453414A1 (en) 2003-01-23
EP1412447A4 (en) 2006-01-04
US7094360B2 (en) 2006-08-22
DE60228846D1 (en) 2008-10-23
CA2453414C (en) 2013-01-15
WO2003006570A2 (en) 2003-01-23
EP1412447A2 (en) 2004-04-28
JP4223394B2 (en) 2009-02-12

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