EP1519931A2 - Composes 3,4-dihydro-2h-pyrane chiraux - Google Patents

Composes 3,4-dihydro-2h-pyrane chiraux

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Publication number
EP1519931A2
EP1519931A2 EP03761553A EP03761553A EP1519931A2 EP 1519931 A2 EP1519931 A2 EP 1519931A2 EP 03761553 A EP03761553 A EP 03761553A EP 03761553 A EP03761553 A EP 03761553A EP 1519931 A2 EP1519931 A2 EP 1519931A2
Authority
EP
European Patent Office
Prior art keywords
mmol
compositions according
crystalline
compounds
variables
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.)
Withdrawn
Application number
EP03761553A
Other languages
German (de)
English (en)
Inventor
Robert Parker
Frank Prechtl
Sylke Haremza
Frank Meyer
Volkmar Vill
Gunnar Gesekus
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1519931A2 publication Critical patent/EP1519931A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
    • C09K2323/031—Polarizer or dye

Definitions

  • the invention relates to chiral 3, 4-dihydro-2ff-pyran compounds and their Diastereo ere and the use of these compounds as chiral dopants for liquid-crystalline systems.
  • the invention further relates to non-polymerizable or polymerizable liquid-crystalline compositions which contain at least one chiral 3, 4-dihydro-2i ⁇ -pyran compound according to the invention, the use of these non-polymerizable or polymerizable liquid-crystalline compositions for the production of optical components, the use of the polymerizable liquid-crystalline compositions for printing or coating substrates, for producing dispersions and emulsions, films or pigments, and also such optical components, printed or coated substrates, dispersions and emulsions, films and pigments.
  • Cholesteric liquid crystal mixtures are usually made using a liquid-crystalline (nematic) base material and one or more optically active dopants.
  • the optical properties of the mixture can be varied by simply changing the ratio of nematic to dopant.
  • dopants are particularly in demand, which cause large changes in the optical properties even in small additions.
  • Chiral dopants for liquid-crystalline phases are known in large numbers from the scientific and patent literature. It is all the more surprising that chiral 3, 4-dihydro-2iT-pyran compounds have obviously not yet been considered as dopants for liquid-crystalline systems.
  • the object of the present invention was to provide further chiral compounds which are suitable for the production of cholesteric-liquid-crystalline compositions, have a relatively high twisting power and accordingly already have a large influence on the optical properties of the liquid-crystalline host system in comparatively small amounts ,
  • This object was achieved according to the invention by the chiral compounds of the general formula I.
  • R 1 and R 2 independently of one another groupings p_yl_ A l_ ⁇ 2_ M _ Y 3_ ( A 2) ⁇ n _ ⁇ 4_
  • Y 1 , Y 2 , Y 3 , Y 4 single chemical bond, -0-, -S-, -C0-, -C0-0-, -O-CO-, -CO-N (R) -, - (R ) N-C0 -, - 0-C0-0-, -O-CO-N (R) -, - (R) N-CO-O- or - (R) N-CO-N (R) -,
  • R is hydrogen or -CC 4 alkyl
  • P is hydrogen, -CC-alkyl, a polymerizable or suitable group for polymerization or a residue which carries a polymerizable or suitable group for polymerization, and
  • variables A 1 , A 2 , Y 1 , Y 2 , ⁇ 3, ⁇ 4, M, P and the index m of the groupings R 1 and R 2 can be the same or different, with the proviso that in the event that the Index m is 0, at least one of the variables Y 3 and Y 4 adjacent to A 2 means a chemical bond.
  • Spacers A 1 and A 2 are all groups known to the person skilled in the art for this purpose.
  • the spacers generally contain one to 30, preferably one to 12, particularly preferably one to six carbon atoms and consist of predominantly linear aliphatic groups. You can in the chain, for example by not Adjacent oxygen or sulfur atoms or I ino or alkyl imino groups such as methylimino groups can be interrupted. Fluorine, chlorine, bromine, cyano, methyl and ethyl can also be used as substituents for the spacer chain.
  • spacers are for example:
  • u is 1 to 30, preferably 1 to 12, v is 1 to 14, preferably 1 to 5, and w is 1 to 9, preferably 1 to 3.
  • Preferred spacers are ethylene, propylene, n-butylene, n-pentylene and n-hexylene.
  • the radicals T can by fluorine, chlorine, bromine, cyano, hydroxyl, foryl, nitro, C 1 -C 20 -alkyl, C 1 -C 20 alkoxy, C 1 -C 20 alkoxycarbonyl, C 1 -C 2 o-monoalkylaminocarbonyl , C ⁇ -Co-alkylcarbonyl, C ⁇ -C 0 alkyl carbonyloxy or C ⁇ -C 0 alkylcarbonylamino substituted ring systems.
  • Preferred radicals T are:
  • the (unsubstituted) mesogenic groups shown above can, of course, in accordance with the examples given above for possible radicals T, also by fluorine, chlorine, bromine, cyano, hydroxyl, formyl, nitro, C 1 -C 20 alkyl, C 1 -C 20 alkoxy , -C-C 20 alkoxycarbonyl, -C-C 20 monoalkylaminocarbonyl, C ⁇ -Co-alkylcarbonyl, C ⁇ -Co-alkylcarbonyloxy or C ⁇ -C 2 o-alkylcarbonylamino substituted.
  • Preferred substituents are, above all, short-chain aliphatic radicals such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl and alkoxy, alkoxycarbonyl, alkylcarbonyl, Alkylcarbonyloxy, alkylcarbonylamino and monoalkylaminocarbonyl radicals which contain these alkyl groups.
  • short-chain aliphatic radicals such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl and alkoxy, alkoxycarbonyl, alkylcarbonyl, Alkylcarbonyloxy, alkylcarbonylamino and monoalkylaminocarbonyl radicals which contain these alkyl groups.
  • Preferred 3,4-dihydro-2i ⁇ -pyran compounds are those in which, in the mesogenic group of the formula Ia of the groups R 1 and R 2, the index r independently of one another assumes the values 0 or 1.
  • C 1 -C 2 alkyl for P are branched or unbranched C 1 -C 4 alkyl chains, for example methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1st , 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1,2 -Dirnethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, -Methylpentyl, 1,1-Dirnethylbutyl, 1,2-Dirnethylbutyl, 1,3-D
  • Preferred alkyl for P are the branched or unbranched Ci-C o -alkyl chains, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dirnethyl - ethyl, n-pentyl, 1-methylb tyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl.
  • Ci-C o -alkyl chains such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dirnethyl - ethyl, n-pentyl, 1-methylb tyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-e
  • P can be considered as a polymerizable or suitable group for polymerisation or as a group bearing a polymerisable or suitable group for polymerisation (hereinafter such groups or groups are simply referred to as "reactive groups”):
  • radicals R 3 to R 5 can be the same or different and are hydrogen or C 1 -C 4 - Alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • the cyanates can trimerize spontaneously to cyanurates.
  • the other groups mentioned require further compounds with complementary reactive groups for the polymerization.
  • isocyanates with alcohols polymerize to urethanes and with a in to urea derivatives.
  • Carboxyl groups can be condensed to polyesters and polyamides.
  • the maleimido group is particularly suitable for radical copolymerization with olefinic compounds, such as styrene or
  • the complementary reactive radicals can be present in one and the same 3, 4-dihydro-2. ⁇ -pyran compound according to the invention (so that this compound can also polymerize with itself) or in a further 3,4-dihydro-2H-pyran compound according to the invention.
  • these complementary reactive radicals can, together with the corresponding reactive radicals, be in one and the same (auxiliary) compounds or in further such (auxiliary) compounds.
  • the acrylate, methacrylate and vinyl radicals are particularly noteworthy.
  • the compounds of the formula I and their preferred embodiments are used as chiral dopants for liquid-crystalline systems.
  • liquid-crystalline systems is not limited to systems in which one or more constituents already have liquid-crystalline properties per se (in the temperature range of interest) and which are also present in the system, but rather systems in which they are to be understood is manifested only by mixing the components or only by adding the chiral compounds (s) according to the invention to liquid-crystalline behavior (eg lyotropic systems). It should also be noted here that the compounds according to the invention need not themselves already have liquid-crystalline behavior.
  • liquid-crystalline and polymerizable liquid-crystalline compositions which contain at least one chiral compound of the formula I or a preferred embodiment.
  • liquid-crystalline compositions here mean in particular non-polymerizable compositions which are not capable of forming polymerization or condensation products under customary conditions.
  • These compositions can be mixed, for example, by mixing suitable, commercially available, liquid-crystalline materials, such as those used for active LC layers in display technology, with one or more of the compounds according to the invention. produce gene.
  • P in formula I corresponds accordingly to hydrogen or C ⁇ -C ⁇ -alkyl.
  • the present invention further relates to polymerizable liquid-crystalline compositions. These are to be understood in particular as those compositions in which at least one of the constituents is capable of forming polymerization or condensation products under customary conditions.
  • the desired degree of polymerization, crosslinking and / or condensation can be set after the polymerization or condensation has taken place.
  • the compounds of the formula I according to the invention have at least one, preferably two reactive radicals P in the groups R 1 and / or R 2 .
  • These compositions can easily be prepared by mixing suitable polymerizable, liquid-crystalline materials with one or more of the compounds according to the invention.
  • Suitable polymerizable, liquid-crystalline compounds are described, for example, in WO 95/22586, 95/24454, 95/24455, 96/04351, 96/24647, 97/00600, 97/34862 and 98/47979 and in German Offenlegungsschrift 198 35 730 described and correspond essentially to the schematic structure PYAYMYAYP, in which the variables P, Y, A and M have meanings similar to the variables P, Y 1 to Y 4 , A 1 , A 2 and M in formula I.
  • the present invention also relates to those optical components which have been obtained using these polymerizable liquid-crystalline compositions according to the invention.
  • the polymerizable liquid-crystalline compositions claimed are used for printing or coating substrates.
  • these compositions other additives.
  • Additives selected from the group consisting of photoinitiators, reactive diluents and diluents, additives selected from the group consisting of defoamers and deaerators, lubricants and leveling aids, thermosetting or radiation-curing aids, substrate wetting aids, wetting and dispersing aids, hydrophobizing agents are suitable as such , Adhesion promoters and auxiliaries for improving the scratch resistance, additives selected from the group consisting of dyes and pigments and additives selected from the group consisting of light, heat and / or oxidation stabilizers.
  • substrates are also goods of (entertainment) electronics, such as MC, MD, DVD and video recorders, televisions, radios, telephones / cell phones etc. and EDP devices, goods from the leisure, sports , Household and game sectors, such as bicycles, children's vehicles, skis, snowboards and surfboards, inline skaters and roller skates and ice skates, and household appliances.
  • such substrates also include writing utensils and spectacle frames.
  • Other substrates are also found in the construction sector, such as building walls or window panes. In the latter case, a functional effect may also be desired in addition to a decorative one. It is thus possible to create multiple layers on the window material, the individual layers of which have different chemical-physical properties.
  • Wavelengths or wavelength ranges of the light spectrum are reflected.
  • an IR or UV reflecting window coating is possible.
  • thermal insulation coatings reference is also made to the document WO 99/19267.
  • the present invention therefore relates to dispersions and emulsions which have been prepared using the polymerizable liquid-crystalline compositions according to the invention. These dispersions and emulsions can also be used for printing and coating substrates, as have already been described above by way of example.
  • the present invention furthermore relates to the use of the polymerizable liquid-crystalline compositions according to the invention for the production of films.
  • films are to be understood in particular as self-supporting layers as are obtained by polymerizing the compositions.
  • These films can be located on substrates or underlays which are designed in such a way that they can be easily detached and transferred to other substrates or underlays for permanent retention by suitable measures.
  • Such Films can be used, for example, in the field of film coating and in laminating processes.
  • the present invention also relates to films which have been produced using the polymerizable liquid-crystalline compositions according to the invention.
  • the polymerizable liquid-crystalline compositions are converted with the aid of their reactive groups and, depending on their chemical nature, by condensation or radical or ionic polymerization processes which can be started by photochemical reactions, into polymers with a frozen liquid-crystalline order structure.
  • These pigments can be single-layer (homogeneous) or have a multi-layer structure. However, the latter pigments can usually only be produced if coating processes are used, in which several layers are successively produced one above the other and then subjected to mechanical comminution.
  • the present invention thus also relates to pigments produced from such polymerizable liquid-crystalline compositions according to the invention.
  • NMR spectroscopy Bruker-AMX 200, Bruker-AMX 400 or DRX 500 in automation mode; 1st order evaluation. TMS was used as the internal standard or calibrated to the characteristic solvent signals.
  • Phase transformations (uncorrected): Olympus BH polarizing microscope with Mettler FP 82 heating table; liquid crystalline phase assignment due to characteristic textures.
  • HTP measurements (HTP: helical twisting water): lens variant of the Grandjean-Cano method, 0.5-6 mol% in ZLI 1840 (commercially available liquid-crystalline product from Merck); Specification of the HTP: 15 ° C below the clearing point.
  • the HTP sign was determined using contact mixtures with cholesteric mesophas known sign by observing the nematic compensation line.
  • AAV-1 esterification using the DCC method (DCC: N, N'-dicyclohexylcarbodiimide)
  • AAV-2 Basic deacetylation with sodium methoxide
  • AAV-3 esterification using the imidazolid method
  • this solution is added dropwise to the initially prepared solution 1 of the carboxylic acid imidazolide under a nitrogen atmosphere and, if appropriate, heated to 40 ° C. to a maximum of 80 ° C. with stirring, depending on the reaction rate. After the end of the reaction, the solvent is removed in vacuo and the crude product is purified as indicated in each case.
  • AAV-4 Basic deacetylation with sodium carbonate
  • AAV-5 esterification of alcohols and phenols with carboxylic acid chlorides
  • AAV-6 Selective deprotection of phenylacetates with guanidine hydrochloride
  • guanidine hydrochloride (Aldrich, purity 99%) is dissolved in 10 ml of anhydrous methanol and stirred with 0.9 equivalents of sodium methoxide for five minutes at room temperature. The mixture is added to a solution of 1 mmol of the phenylacetate in 50 ml of methanol, and the resulting methyl acetate is removed at 40 ° C. and 270 mbar on a rotary evaporator together with the solvent.
  • the processing can be carried out according to two methods:
  • Method 1 The reaction mixture, which is evaporated to dryness in vacuo, is mixed with 50 ml of hydrochloric acid and dichloromethane and stirred until no undissolved residues are left. The organic phase is separated off, the aqueous phase is extracted several times with dichloromethane, the combined organic phases are dried over magnesium sulfate and the solvent is removed in vacuo.
  • the combined organic phases are washed neutral with saturated sodium bicarbonate solution, washed with 250 ml of water and dried over magnesium sulfate. Then activated carbon is added, after stirring for a quarter of an hour the activated carbon is filtered off and the solvent is removed.
  • the mixture is stirred for a further 1 h at 0 ° C. and then for a further 1.25 h at room temperature.
  • the filter residue is washed with an acetic acid / water mixture (1: 1).
  • the solution is then extracted once with ice water and three times with cold chloroform and the combined organic phases are neutralized with sodium hydrogen carbonate.
  • the solution is dried over magnesium sulfate and the solvent is removed in vacuo.
  • the product is purified by flash chromatography using silica gel filtration (petroleum ether (50/70) / diethyl ether, 3: 1).
  • the mixture is stirred at 0 ° C. for 1 h and then at room temperature for a further 1.25 h.
  • the filter residue is washed with a vinegar acid / water mixture (1: 1) washed.
  • the solution is then extracted once with ice water and three times with cold chloroform and the combined organic phases are neutralized with sodium bicarbonate.
  • the solution is dried over magnesium sulfate and the solvent is removed.
  • the product is purified by flash chromatography using column filtration (petroleum ether (50/70) / diethyl ether, 3: 1).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne des composés 3,4-dihydro-2H-pyrane chiraux, leurs diastéréomères et leur utilisation en tant qu'agents de dopage chiraux destinés à des systèmes cristallins liquides. L'invention concerne également des compositions cristallines liquides polymérisables ou non, contenant au moins un composé 3,4-dihydro-2H-pyrane selon l'invention, l'utilisation de ces compositions cristallines liquides polymérisables ou non dans la fabrication de composants optiques, l'utilisation des compositions cristallines liquides polymérisables pour l'impression ou le revêtement de substrats, la fabrication de dispersions et d'émulsions, de pellicules ou de pigments, les composants optiques, les substrats imprimés ou revêtus, les dispersions et émulsions et les pellicules et pigments.
EP03761553A 2002-07-01 2003-06-30 Composes 3,4-dihydro-2h-pyrane chiraux Withdrawn EP1519931A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10229530A DE10229530A1 (de) 2002-07-01 2002-07-01 Chirale 3,4-Dihydro-2H-pyranverbindungen
DE10229530 2002-07-01
PCT/EP2003/006885 WO2004002979A2 (fr) 2002-07-01 2003-06-30 Composes 3,4-dihydro-2h-pyrane chiraux

Publications (1)

Publication Number Publication Date
EP1519931A2 true EP1519931A2 (fr) 2005-04-06

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EP03761553A Withdrawn EP1519931A2 (fr) 2002-07-01 2003-06-30 Composes 3,4-dihydro-2h-pyrane chiraux

Country Status (7)

Country Link
US (1) US7258902B2 (fr)
EP (1) EP1519931A2 (fr)
JP (1) JP2005538969A (fr)
CN (1) CN100400532C (fr)
AU (1) AU2003250860A1 (fr)
DE (1) DE10229530A1 (fr)
WO (1) WO2004002979A2 (fr)

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US9127362B2 (en) 2005-10-31 2015-09-08 Applied Materials, Inc. Process kit and target for substrate processing chamber
JP2007310871A (ja) 2006-04-19 2007-11-29 Ricoh Co Ltd 発注支援システム、発注支援装置、機器監視装置、発注支援方法、機器監視方法及びプログラム
CN101289439B (zh) * 2007-04-16 2011-04-06 中国科学院成都生物研究所 一种制备阿拉伯烯糖的方法
US8968536B2 (en) 2007-06-18 2015-03-03 Applied Materials, Inc. Sputtering target having increased life and sputtering uniformity
US8168084B2 (en) 2009-12-18 2012-05-01 Vanderbilt University Polar nematic compounds
DE102010034243A1 (de) * 2010-08-13 2012-02-16 Clariant International Limited Verfahren zur Herstellung von Acyloxybenzoesäuren
DE102010034244A1 (de) * 2010-08-13 2012-02-16 Clariant International Limited Verfahren zur Herstellung von Acyloxybenzoesäuren

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Also Published As

Publication number Publication date
US7258902B2 (en) 2007-08-21
AU2003250860A1 (en) 2004-01-19
AU2003250860A8 (en) 2004-01-19
DE10229530A1 (de) 2004-01-15
CN1735606A (zh) 2006-02-15
WO2004002979A2 (fr) 2004-01-08
WO2004002979A3 (fr) 2004-04-22
CN100400532C (zh) 2008-07-09
JP2005538969A (ja) 2005-12-22
US20050230660A1 (en) 2005-10-20

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