DE69003712T2 - Optisch aktive Verbindungen, ihre Herstellung und Verwendung. - Google Patents
Optisch aktive Verbindungen, ihre Herstellung und Verwendung.Info
- Publication number
- DE69003712T2 DE69003712T2 DE90105444T DE69003712T DE69003712T2 DE 69003712 T2 DE69003712 T2 DE 69003712T2 DE 90105444 T DE90105444 T DE 90105444T DE 69003712 T DE69003712 T DE 69003712T DE 69003712 T2 DE69003712 T2 DE 69003712T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- compound
- liquid crystal
- formula
- optically active
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims description 152
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000004973 liquid crystal related substance Substances 0.000 claims description 85
- -1 carbonyldioxy group Chemical group 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 15
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 239000012071 phase Substances 0.000 description 39
- 239000000126 substance Substances 0.000 description 26
- 239000004990 Smectic liquid crystal Substances 0.000 description 23
- 230000010287 polarization Effects 0.000 description 23
- 230000002269 spontaneous effect Effects 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 238000000921 elemental analysis Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- 230000004044 response Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000004988 Nematic liquid crystal Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 9
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- IOWBOGZNODYSOJ-IUCAKERBSA-N (2s,5s)-5-propoxyhexan-2-ol Chemical compound CCCO[C@@H](C)CC[C@H](C)O IOWBOGZNODYSOJ-IUCAKERBSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 150000003333 secondary alcohols Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- KJPIQAYHGCWRBL-UHFFFAOYSA-N (4-octoxyphenyl) 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1OC(=O)C1=CC=C(C=2C=CC(O)=CC=2)C=C1 KJPIQAYHGCWRBL-UHFFFAOYSA-N 0.000 description 5
- 230000003098 cholesteric effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HJKJATDIBSTRCI-UHFFFAOYSA-N 2-methyl-5-(3-methylpentoxy)hexanoic acid Chemical compound CCC(C)CCOC(C)CCC(C)C(O)=O HJKJATDIBSTRCI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 101150018444 sub2 gene Proteins 0.000 description 4
- 150000003459 sulfonic acid esters Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GALGQYZZRHASJT-IUCAKERBSA-N (2s,5s)-2-methyl-5-propoxyhexanoic acid Chemical compound CCCO[C@@H](C)CC[C@H](C)C(O)=O GALGQYZZRHASJT-IUCAKERBSA-N 0.000 description 3
- JWEMTNRIRJMLEA-UWVGGRQHSA-N (2s,5s)-5-butoxyhexan-2-ol Chemical compound CCCCO[C@@H](C)CC[C@H](C)O JWEMTNRIRJMLEA-UWVGGRQHSA-N 0.000 description 3
- PFPKJPNLWZMSQY-BQBZGAKWSA-N (2s,5s)-5-methoxyhexan-2-ol Chemical compound CO[C@@H](C)CC[C@H](C)O PFPKJPNLWZMSQY-BQBZGAKWSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- JMPYNFPVYOTMQM-UHFFFAOYSA-N 3-methylpentyl 5-hydroxy-2-methylhexanoate Chemical compound CCC(C)CCOC(=O)C(C)CCC(C)O JMPYNFPVYOTMQM-UHFFFAOYSA-N 0.000 description 3
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000011914 asymmetric synthesis Methods 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 3
- GALGQYZZRHASJT-BDAKNGLRSA-N (2r,5s)-2-methyl-5-propoxyhexanoic acid Chemical compound CCCO[C@@H](C)CC[C@@H](C)C(O)=O GALGQYZZRHASJT-BDAKNGLRSA-N 0.000 description 2
- HKONPYGBHSTZGV-BDAKNGLRSA-N (2r,5s)-2-methyl-5-propoxyhexanoyl chloride Chemical compound CCCO[C@@H](C)CC[C@@H](C)C(Cl)=O HKONPYGBHSTZGV-BDAKNGLRSA-N 0.000 description 2
- JWEMTNRIRJMLEA-ZJUUUORDSA-N (2r,5s)-5-butoxyhexan-2-ol Chemical compound CCCCO[C@@H](C)CC[C@@H](C)O JWEMTNRIRJMLEA-ZJUUUORDSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- VKMLCPHQDWRURW-UHFFFAOYSA-N 4-(4-octoxyphenyl)phenol Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(O)C=C1 VKMLCPHQDWRURW-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HMODRDMCPPHONO-UHFFFAOYSA-N 5-(2-methylpropoxy)hexan-2-ol Chemical compound CC(C)COC(C)CCC(C)O HMODRDMCPPHONO-UHFFFAOYSA-N 0.000 description 2
- IMNMMXDEBXTVPH-UHFFFAOYSA-N 5-decoxy-2-methylhexanoic acid Chemical compound CCCCCCCCCCOC(C)CCC(C)C(O)=O IMNMMXDEBXTVPH-UHFFFAOYSA-N 0.000 description 2
- ROQLZIOBSIMKMY-UHFFFAOYSA-N 5-decoxyhexan-2-ol Chemical compound CCCCCCCCCCOC(C)CCC(C)O ROQLZIOBSIMKMY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000000023 Kugelrohr distillation Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- NYPJWEVCAYRMIB-UHFFFAOYSA-N nonyl 5-hydroxy-2-methylhexanoate Chemical compound CCCCCCCCCOC(=O)C(C)CCC(C)O NYPJWEVCAYRMIB-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- CCKOJFAKXOCCGB-UHFFFAOYSA-N octyl 5-hydroxy-2-methylhexanoate Chemical compound CCCCCCCCOC(=O)C(C)CCC(C)O CCKOJFAKXOCCGB-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- KCCNVKOOZCVKPP-UHFFFAOYSA-N pentyl 5-hydroxy-2-methylhexanoate Chemical compound CCCCCOC(=O)C(C)CCC(C)O KCCNVKOOZCVKPP-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VBRICUYSAKFSKM-UHFFFAOYSA-N propan-2-yl 5-hydroxy-2-methylhexanoate Chemical compound CC(C)OC(=O)C(C)CCC(C)O VBRICUYSAKFSKM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- KNFRRLGNIRERSX-UHFFFAOYSA-N propyl 5-hydroxy-2-methylhexanoate Chemical compound CCCOC(=O)C(C)CCC(C)O KNFRRLGNIRERSX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
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- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K19/126—Compounds containing at least one asymmetric carbon atom
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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
- C09K19/10—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
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/28—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 sulfur atoms as chain links, e.g. thioesters
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- 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
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3455—Pyridazine
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
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- 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
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Claims (12)
1. Optisch aktive Verbindungen der allgemeinen Formel I,
in der bedeuten:
R&sub1; C&sub3;&submin;&sub1;&sub4;-Alkyl oder C&sub3;&submin;&sub1;&sub4;-Alkenyl;
R&sub2; und R&sub3; unabhängig C&sub1;&submin;&sub3;-Alkyl;
R&sub4; C&sub1;&submin;&sub1;&sub0;-Alkyl;
Q&sub1;, Q&sub2; und Q&sub3; unabhängig eine Einfachbindung, eine
(Thio)ethergruppe, eine
(Thio)carbonsäureestergruppe, eine Carbonylgruppe oder eine
Carbonyldioxygruppe;
M
wobei X und Y unabhängig eine Einfachbindung, eine
(Thio)carbonsäureestergruppe, eine
Methylenoxygruppe oder eine Ethylengruppe und
unabhängig eine 6-Ring-1,4-diylgruppe,
die 1 bis 2 Sauerstoff- oder Stickstoffatome im
Ring aufweisen kann, darstellen;
n eine ganze Zahl von 2 bis 6,
wobei die mit Stern (*) bezeichneten Kohlenstoffatome
asymmetrische Kohlenstoffatome darstellen.
2. Optisch aktive Verbindungen nach Anspruch 1, in deren
Formel
die gleich oder verschieden sein können, p-Phenylen,
1,4-Cycohexylen, 2,5-(1,3-Dioxan)-diyl,
2,5-Pyridindiyl, 2,5-Pyrimidindiyl, 2,5-(1,4-Pyrazin)-diyl oder
3,6-(1,2-Pyridazin)-diyl bedeuten.
3. Optisch aktive Verbindungen nach Anspruch 1 oder 2, in
deren Formel M
bedeutet, wobei eine der Brücken X and Y eine
Einfachbindung und die andere eine Carbonsäureestergruppe
und
p-Phenylen darstellen.
4. Optisch aktive Verbindungen nach einem der Ansprüche 1
bis 3, in deren Formel M
bedeutet, wobei X eine Einfachbindung und
p-Phenylen darstellen.
5. Optisch aktive Verbindungen nach einem der Ansprüche 1
bis 4, die folgende Formeln aufweisen:
6. Chirale Verbindungen der allgemeinen Formel VI
in der bedeuten:
R&sub2; und R&sub3; unabhängig C&sub1;&submin;&sub3;-Alkyl;
R&sub4; C&sub1;&submin;&sub1;&sub0;-Alkyl;
Q&sub3; eine (Thio)ethergruppe, eine
(Thiocarbonsäureestergruppe, eine Carbonylgruppe oder eine
Carbonyldioxygruppe;
Z eine Hydroxygruppe, eine Thiolgruppe, eine
Carboxygruppe oder eine Thiocarboxygruppe
und
n eine ganze Zahl von 2 bis 6.
7. Chirale Verbindungen nach Anspruch 6, in deren Formel n
2 bedeutet.
8. Flüssigkristallzusammensetzungen, die mindestens eine
optisch aktive Verbindung der Formel I nach einem der
Ansprüche 1 bis 5 und wahlweise einen
Mutter-Flüssigkristall enthalten.
9. Optische Flüssigkristall-Anzeigevorrichtungen und
optiche Flüssigkristallmodulatoren, die mindestens zwei
Substrate und eine zwischen den Substraten vorgesehene
Flüssigkristallzusammensetzung aufweisen, dadurch
gekennzeichnet, daß die Flüssigkristallzusammensetzung
mindestens eine optisch aktive Verbindung der Formel I
nach einem der Ansprüche 1 bis 5 enthält, oder
dadurch gekennzeichnet, daß die
Flüssigkristallzusammensetzung eine Flüssigkristallzusammensetzung nach
Anspruch 8 ist.
10. Verfahren zur Herstellung der optisch aktiven
Verbindungen der Formel I nach einem der Ansprüche 1 bis 5,
gekennzeichnet durch
Umsetzung einer dichiralen Verbindung der allgemeinen
Formel VI,
in der bedeuten:
R&sub2; und R&sub3; unabhängig C&sub1;&submin;&sub3;-Alkyl;
R&sub4; C&sub1;&submin;&sub1;&sub0;-Alkyl;
Q&sub3; eine (Thio)ethergruppe, eine
(Thio)carbonsäureestergruppe, eine Carbonylgruppe
oder eine Carbonyldioxygruppe;
Z Halogen, eine Hydroxygruppe, eine
Thiolgruppe, eine Carboxygruppe oder eine
Thiocarboxygruppe oder ein reaktives Derivat
einer dieser Gruppen
und
n eine ganze Zahl von 2 bis 6,
mit einer Verbindung der allgemeinen Formel VII,
R&sub1;-Q&sub1;-M-R&sub5; (VII),
in der bedeuten:
R&sub1; C&sub3;&submin;&sub1;&sub4;-Alkyl oder C&sub3;&submin;&sub1;&sub4;-Alkenyl;
Q&sub1; eine Einfachbindung, eine (Thio)ethergruppe, eine
(Thio)carbonsäureestergruppe, eine Carbonylgruppe
oder eine Carbonyldioxygruppe;
M
wobei X und Y unabhängig eine Einfachbindung, eine
(Thio)carbonsäureestergruppe eine
Methylenoxygruppe oder eine Ethylengruppe und
unabhängig eine 6-Ring-1,4-diylgruppe darstellen,
die 1 bis 2 Sauerstoff- oder Stickstoffatome im
Ring enthalten kann,
und
R&sub5; Halogen, eine Hydroxygruppe, eine Thiolgruppe, eine
Carboxygruppe oder eine Thiocarboxygruppe oder ein
reaktives Derivat einer dieser Gruppen.
11. Verfahren nach Anspruch 10,
gekennzeichnet durch
(A) Umsetzung einer Verbindung der Formel III
mit einer Verbindung der Formel II
R&sub1;-Q&sub1;-M-COOH (II)
oder
(B) Umsetzung einer Verbindung der Formel III wie oben
definiert mit einer Verbindung der Formel IVa
R&sub1;-Q&sub1;-M-OH (IVa)
oder einer Verbindung der Formel IVb
R&sub1;-Q&sub1;-M-SH (IVb)
oder
(C) Umsetzung einer Verbindung der Formel V
mit einer Verbindung der Formel IVa wie oben
definiert,
wobei R&sub1;, R&sub2;, R&sub3;, R&sub4;, Q&sub1;, Q&sub3;, M und n wie in
Anspruch 10 definiert sind.
12. Verfahren nach Anspruch 11, dadurch gekennzeichnet,
daß die Verbindung der Formel III in Form des
entsprechenden Trimethylsilyletherderivats der Formel
eingesetzt und der Ether mit einem
Säurehalogenidderivat der Verbindung der Formel II in Gegenwart
einer Lewissäure kondensiert wird.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP6756189 | 1989-03-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69003712D1 DE69003712D1 (de) | 1993-11-11 |
DE69003712T2 true DE69003712T2 (de) | 1994-04-14 |
Family
ID=13348494
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE90105444T Expired - Fee Related DE69003712T2 (de) | 1989-03-22 | 1990-03-22 | Optisch aktive Verbindungen, ihre Herstellung und Verwendung. |
Country Status (4)
Country | Link |
---|---|
US (1) | US5152919A (de) |
EP (1) | EP0388960B1 (de) |
KR (1) | KR900014300A (de) |
DE (1) | DE69003712T2 (de) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH02138235A (ja) * | 1988-07-20 | 1990-05-28 | Takeda Chem Ind Ltd | 光学活性化合物、同中間体、該化合物を含有する液晶組成物及び該液晶組成物を用いた液晶光変調装置 |
US5269965A (en) * | 1988-12-28 | 1993-12-14 | Takeda Chemical Industries | Optically active compounds, liquid crystal compositions comprising said compounds and liquid crystal optical modulators using said compositions |
DE68925954T2 (de) * | 1988-12-28 | 1996-10-17 | Hitachi Ltd | Optisch aktive Verbindungen, sie enthaltende flüssigkristalline Zusammensetzungen und optische Modulatoren auf Flüssigkristallbasis unter Verwendung dieser Zusammensetzungen |
US5380460A (en) * | 1991-09-20 | 1995-01-10 | Displaytech, Inc. | Ferroelectric liquid crystal compounds containing chiral haloalkoxy tail units and compositions containing them |
JPH0749416B2 (ja) * | 1990-10-31 | 1995-05-31 | 三星電管株式會社 | 光学活性脂肪族α−ハロゲン置換カルボン酸4’−(4−アルコキシフェニルチオオキソ)ビフェニリルエステル系化合物及びその製造方法 |
US5366659A (en) * | 1994-03-22 | 1994-11-22 | Industrial Technology Research Institute | Ferroelectric liquid crystals containing pyrimidine and chiral compounds and liquid crystal compositions containing the same |
US5896368A (en) * | 1995-05-01 | 1999-04-20 | Telefonaktiebolaget Lm Ericsson | Multi-code compressed mode DS-CDMA systems and methods |
US5883899A (en) * | 1995-05-01 | 1999-03-16 | Telefonaktiebolaget Lm Ericsson | Code-rate increased compressed mode DS-CDMA systems and methods |
US6854888B1 (en) * | 2000-01-28 | 2005-02-15 | Dennis B. Brown | Multispout flask with pump |
US20020198520A1 (en) * | 2001-06-20 | 2002-12-26 | Scimed Life Systems, Inc. | Irrigation sheath |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE3577843D1 (de) * | 1984-09-10 | 1990-06-28 | Ajinomoto Kk | Biphenyldiesterverbindungen und fluessigkristallkompositionen die diese enthalten. |
GB2170214A (en) * | 1985-01-26 | 1986-07-30 | Stc Plc | Ferroelectric smectic liquid crystal mixture |
US4959173A (en) * | 1987-09-29 | 1990-09-25 | Adeka Argus Chemical Co., Ltd. | Optically active ester compound |
KR890010157A (ko) * | 1987-12-24 | 1989-08-07 | 미다 가쓰기게 | 광학활성 화합물, 이 화합물을 함유한 액정 조성물 및 이 조성물을 사용한 액정 광 변조장치 |
US4954600A (en) * | 1988-06-27 | 1990-09-04 | Idemitsu Kosan Co., Ltd. | Ferroelectric liquid-crystalline polymer and epoxide usable to preparation of the ferroelectric liquid-crystalline polymer |
JP2782075B2 (ja) * | 1989-02-14 | 1998-07-30 | 旭電化工業株式会社 | 光学活性な化合物および該化合物を含有する液晶組成物 |
-
1990
- 1990-03-21 KR KR1019900003806A patent/KR900014300A/ko not_active Application Discontinuation
- 1990-03-22 US US07/497,269 patent/US5152919A/en not_active Expired - Fee Related
- 1990-03-22 EP EP90105444A patent/EP0388960B1/de not_active Expired - Lifetime
- 1990-03-22 DE DE90105444T patent/DE69003712T2/de not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0388960A1 (de) | 1990-09-26 |
KR900014300A (ko) | 1990-10-23 |
EP0388960B1 (de) | 1993-10-06 |
DE69003712D1 (de) | 1993-11-11 |
US5152919A (en) | 1992-10-06 |
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