JPS6230981B2 - - Google Patents
Info
- Publication number
- JPS6230981B2 JPS6230981B2 JP58137800A JP13780083A JPS6230981B2 JP S6230981 B2 JPS6230981 B2 JP S6230981B2 JP 58137800 A JP58137800 A JP 58137800A JP 13780083 A JP13780083 A JP 13780083A JP S6230981 B2 JPS6230981 B2 JP S6230981B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- methylbutoxycarbonyl
- ester
- phenyl ester
- liquid crystal
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 2
- -1 phenyl ester Chemical class 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- BDDYPNQQJHNKSC-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 BDDYPNQQJHNKSC-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- YCVMFKRVGOAHAA-UHFFFAOYSA-N 2-methylbutyl 4-hydroxybenzoate Chemical compound CCC(C)COC(=O)C1=CC=C(O)C=C1 YCVMFKRVGOAHAA-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- MEKMFJJJRBEBLC-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-octylbenzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 MEKMFJJJRBEBLC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 1
- WYUVZDIOIFXZSJ-UHFFFAOYSA-N 2-methylbutyl 4-(4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C1=CC=C(O)C=C1 WYUVZDIOIFXZSJ-UHFFFAOYSA-N 0.000 description 1
- PPNWJQBUTHYDRL-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-butoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 PPNWJQBUTHYDRL-UHFFFAOYSA-N 0.000 description 1
- LEMLLQAUUJUYTR-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-decoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 LEMLLQAUUJUYTR-UHFFFAOYSA-N 0.000 description 1
- PTBABFRHRGKTHT-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-ethoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 PTBABFRHRGKTHT-UHFFFAOYSA-N 0.000 description 1
- FDNOLFFPGNEBQO-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-heptoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 FDNOLFFPGNEBQO-UHFFFAOYSA-N 0.000 description 1
- RQIYAPXOLSDSMX-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-hexadecoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 RQIYAPXOLSDSMX-UHFFFAOYSA-N 0.000 description 1
- MKEIINRIUKFPNQ-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-hexoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 MKEIINRIUKFPNQ-UHFFFAOYSA-N 0.000 description 1
- OQIMACBVHZCZIJ-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-icosoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 OQIMACBVHZCZIJ-UHFFFAOYSA-N 0.000 description 1
- COJKHJWCBDNXFM-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-methoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C(C=C1)=CC=C1OC(=O)C1=CC=C(OC)C=C1 COJKHJWCBDNXFM-UHFFFAOYSA-N 0.000 description 1
- IPUQGWMTSRPULR-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-tetradecoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 IPUQGWMTSRPULR-UHFFFAOYSA-N 0.000 description 1
- KMIJMCGRSGAUQE-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-tridecoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 KMIJMCGRSGAUQE-UHFFFAOYSA-N 0.000 description 1
- MLLWCMIDWKRNBH-UHFFFAOYSA-N 2-methylbutyl 4-[4-(4-undecoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 MLLWCMIDWKRNBH-UHFFFAOYSA-N 0.000 description 1
- BVBTVBVHIQDKKW-UHFFFAOYSA-N 4-(4-butylphenyl)benzoic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 BVBTVBVHIQDKKW-UHFFFAOYSA-N 0.000 description 1
- JOEUACGJYOALBK-UHFFFAOYSA-N 4-(4-decylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 JOEUACGJYOALBK-UHFFFAOYSA-N 0.000 description 1
- ODJQBLRUMXTLKR-UHFFFAOYSA-N 4-(4-dodecylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ODJQBLRUMXTLKR-UHFFFAOYSA-N 0.000 description 1
- SCEBDBNGUCNRCE-UHFFFAOYSA-N 4-(4-ethylphenyl)benzoic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(O)=O)C=C1 SCEBDBNGUCNRCE-UHFFFAOYSA-N 0.000 description 1
- JQYOLOUWMFQPHX-UHFFFAOYSA-N 4-(4-heptadecylphenyl)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O JQYOLOUWMFQPHX-UHFFFAOYSA-N 0.000 description 1
- XVROSBHWACAQRL-UHFFFAOYSA-N 4-(4-heptylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 XVROSBHWACAQRL-UHFFFAOYSA-N 0.000 description 1
- QOSUFFMGYFKMER-UHFFFAOYSA-N 4-(4-hexadecoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 QOSUFFMGYFKMER-UHFFFAOYSA-N 0.000 description 1
- VRZAITLEVINCDJ-UHFFFAOYSA-N 4-(4-hexadecylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VRZAITLEVINCDJ-UHFFFAOYSA-N 0.000 description 1
- ROJCBWVSXWIGAL-UHFFFAOYSA-N 4-(4-hexylphenyl)benzoic acid Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ROJCBWVSXWIGAL-UHFFFAOYSA-N 0.000 description 1
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 1
- TZHLKIARQVJZHE-UHFFFAOYSA-N 4-(4-icosoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 TZHLKIARQVJZHE-UHFFFAOYSA-N 0.000 description 1
- BMBOGKGRAXXPJS-UHFFFAOYSA-N 4-(4-icosylphenyl)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O BMBOGKGRAXXPJS-UHFFFAOYSA-N 0.000 description 1
- RZOCCLOTCXINRG-UHFFFAOYSA-N 4-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 RZOCCLOTCXINRG-UHFFFAOYSA-N 0.000 description 1
- JQKADZIIOIYSEQ-UHFFFAOYSA-N 4-(4-nonadecoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 JQKADZIIOIYSEQ-UHFFFAOYSA-N 0.000 description 1
- YJORVTGGKVLJNI-UHFFFAOYSA-N 4-(4-nonadecylphenyl)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O YJORVTGGKVLJNI-UHFFFAOYSA-N 0.000 description 1
- JEDSQOLKNJLVRX-UHFFFAOYSA-N 4-(4-nonylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 JEDSQOLKNJLVRX-UHFFFAOYSA-N 0.000 description 1
- NQYQFSNKMLDZII-UHFFFAOYSA-N 4-(4-octadecylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 NQYQFSNKMLDZII-UHFFFAOYSA-N 0.000 description 1
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 1
- HXBKPYIEQLLNBK-UHFFFAOYSA-N 4-(4-octylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HXBKPYIEQLLNBK-UHFFFAOYSA-N 0.000 description 1
- NYWWEYNOHIPCDA-UHFFFAOYSA-N 4-(4-pentadecoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 NYWWEYNOHIPCDA-UHFFFAOYSA-N 0.000 description 1
- VDYOWJRZVSNETK-UHFFFAOYSA-N 4-(4-pentadecylphenyl)benzoic acid Chemical compound C(CCCCCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O VDYOWJRZVSNETK-UHFFFAOYSA-N 0.000 description 1
- VRGQQLFRUKMDSW-UHFFFAOYSA-N 4-(4-pentylphenyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VRGQQLFRUKMDSW-UHFFFAOYSA-N 0.000 description 1
- HCPBURTZSXRGBN-UHFFFAOYSA-N 4-(4-propylphenyl)benzoic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HCPBURTZSXRGBN-UHFFFAOYSA-N 0.000 description 1
- VBEJKSVWOYFIKQ-UHFFFAOYSA-N 4-(4-tetradecoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VBEJKSVWOYFIKQ-UHFFFAOYSA-N 0.000 description 1
- JZCDYKTXEJTJFP-UHFFFAOYSA-N 4-(4-tetradecylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 JZCDYKTXEJTJFP-UHFFFAOYSA-N 0.000 description 1
- QOKBSRFIZDVHRW-UHFFFAOYSA-N 4-(4-tridecylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 QOKBSRFIZDVHRW-UHFFFAOYSA-N 0.000 description 1
- HLUFYSVGNWSCMG-UHFFFAOYSA-N 4-(4-undecoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HLUFYSVGNWSCMG-UHFFFAOYSA-N 0.000 description 1
- ZRVIYEJYXIDATJ-UHFFFAOYSA-N 4-Heptyloxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1 ZRVIYEJYXIDATJ-UHFFFAOYSA-N 0.000 description 1
- QFPMTKPMXXKCNW-UHFFFAOYSA-N 4-decoxybenzoyl chloride Chemical compound CCCCCCCCCCOC1=CC=C(C(Cl)=O)C=C1 QFPMTKPMXXKCNW-UHFFFAOYSA-N 0.000 description 1
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 description 1
- NEKGDYGTJYCIRI-UHFFFAOYSA-N 4-octylbenzoyl chloride Chemical compound CCCCCCCCC1=CC=C(C(Cl)=O)C=C1 NEKGDYGTJYCIRI-UHFFFAOYSA-N 0.000 description 1
- UNWMYCGHDMYGRF-UHFFFAOYSA-N 4-pentadecylbenzoic acid Chemical compound CCCCCCCCCCCCCCCC1=CC=C(C(O)=O)C=C1 UNWMYCGHDMYGRF-UHFFFAOYSA-N 0.000 description 1
- COKCXCGVFMMUTO-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-butylbenzoate Chemical compound C1=CC(CCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 COKCXCGVFMMUTO-UHFFFAOYSA-N 0.000 description 1
- XLIAICAWBHIACY-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-decylbenzoate Chemical compound C1=CC(CCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 XLIAICAWBHIACY-UHFFFAOYSA-N 0.000 description 1
- FLLWVQZQSVCRHQ-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-dodecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 FLLWVQZQSVCRHQ-UHFFFAOYSA-N 0.000 description 1
- GVNBPESHLPSRPO-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-ethylbenzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C(C=C1)=CC=C1OC(=O)C1=CC=C(CC)C=C1 GVNBPESHLPSRPO-UHFFFAOYSA-N 0.000 description 1
- MRVWYHZLVZWMLT-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-heptadecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 MRVWYHZLVZWMLT-UHFFFAOYSA-N 0.000 description 1
- KAOHNQATQBEIAN-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-heptylbenzoate Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 KAOHNQATQBEIAN-UHFFFAOYSA-N 0.000 description 1
- SFHIFURORMDABR-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-hexadecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 SFHIFURORMDABR-UHFFFAOYSA-N 0.000 description 1
- OVEAVBKJDKNHQX-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-hexylbenzoate Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 OVEAVBKJDKNHQX-UHFFFAOYSA-N 0.000 description 1
- HKQODSNHSOJARX-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-icosylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 HKQODSNHSOJARX-UHFFFAOYSA-N 0.000 description 1
- NFEBHNFODKMXEP-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-methylbenzoate Chemical compound C1=CC(C(=O)OCC(C)CC)=CC=C1C(C=C1)=CC=C1OC(=O)C1=CC=C(C)C=C1 NFEBHNFODKMXEP-UHFFFAOYSA-N 0.000 description 1
- AAQLIXPBQQZYQF-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-nonadecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 AAQLIXPBQQZYQF-UHFFFAOYSA-N 0.000 description 1
- RVSKAPMUCSEULM-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-nonylbenzoate Chemical compound C1=CC(CCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 RVSKAPMUCSEULM-UHFFFAOYSA-N 0.000 description 1
- ZKVVHMVHYVPIDV-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-octadecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 ZKVVHMVHYVPIDV-UHFFFAOYSA-N 0.000 description 1
- MTNSCJXIIJEMNJ-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-pentadecylbenzoate Chemical compound C1=CC(CCCCCCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 MTNSCJXIIJEMNJ-UHFFFAOYSA-N 0.000 description 1
- UZFWGGRERMOCJU-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 UZFWGGRERMOCJU-UHFFFAOYSA-N 0.000 description 1
- URBGFAPJFMCAMZ-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-propylbenzoate Chemical compound C1=CC(CCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 URBGFAPJFMCAMZ-UHFFFAOYSA-N 0.000 description 1
- OUQCOAWCORQNSM-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyl)phenyl]phenyl] 4-undecylbenzoate Chemical compound C1=CC(CCCCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OCC(C)CC)C=C1 OUQCOAWCORQNSM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000003464 asthenopia Diseases 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- OZCQSLCWVXQYNY-UHFFFAOYSA-N octan-2-yl 4-[4-(4-octoxybenzoyl)oxyphenyl]benzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C=2C=CC(=CC=2)C(=O)OC(C)CCCCCC)C=C1 OZCQSLCWVXQYNY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
〔発明の利用分野〕
本発明は液晶性化合物と該液晶性化合物を含む
液晶組成物に関する。
〔発明の背景〕
現在、液晶表示は広く実用に供されているが、
その大部分はTN〔ツイステツド ネマテイツク
（Twisted Nematic）〕型表示方式を採用してい
る。TN型表示方式は消費電力が少なく、受光型
であるために目の疲労が少ない等の長所を有する
が、反面応答速度が遅い欠点を持つ。最近の表示
装置に対する要求は特に高速応答が望まれる傾向
にあり、これに対処すべく液晶材料の改良が行わ
れている。しかし、発光型の表示方式（例えば発
光ダイオード、EL、プラズマデイスプレイ等）
と比較すると応答時間にはまだ大きな差がある。
受光型で低消費電力である液晶表示の長所を生か
し、しかも高速応答できる新しい表示方式を見出
すことが続けられている。そのような試みの１つ
に強誘電性液晶の光スイツチング現象を利用した
表示デバイス〔例えば、N.A.クラーク（N.A.
Clark）、S.T.ラガーヴアール（S.T.
Lagerwall）、アプライド フイジツクス レタ
ース（Appl.Phys.Lett.），36，899（1980）〕があ
る。強誘電性液晶はR.B.メイヤー（R.B.Meyer）
らにより見出され〔R.B.メイヤー等、ズルナル
ド フイジク（J.Physique，36，Ｌ―69
（1975）〕たもので、分子配列上からカイラルスメ
クチツクＣ（以下、ＳC *と略記する）相あるい
はカイラルスメクチツクＨ（以下、ＳH *と略記
する）相に属するとされている。現在までに強誘
電性液晶性化合物としては表１に示す化合物が知
られている〔Ph.マルチノラガー（Ph.Martino
Lagarde）、ズルナル ド フイジク（J.
Physique，37，C3―129（1976）〕。
[Field of Application of the Invention] The present invention relates to a liquid crystal compound and a liquid crystal composition containing the liquid crystal compound. [Background of the Invention] Currently, liquid crystal displays are widely used in practical use.
Most of them use the TN (Twisted Nematic) type display system. The TN display system has advantages such as low power consumption and less eye fatigue because it is a light-receiving type, but it has the disadvantage of slow response speed. Recent demands for display devices are particularly toward high-speed response, and improvements are being made to liquid crystal materials to meet this demand. However, light-emitting display methods (e.g. light-emitting diode, EL, plasma display, etc.)
There is still a large difference in response time compared to
New display methods that take advantage of the advantages of light-receiving, low power consumption liquid crystal displays and high-speed response are being discovered. One such attempt is a display device that utilizes the optical switching phenomenon of ferroelectric liquid crystals [for example, NA Clark (NA
Clark), ST Lagarveard (ST
Lagerwall, Applied Physics Letters, 36 , 899 (1980). Ferroelectric liquid crystal is manufactured by RB Meyer
[RB Mayer et al., J.Physique, 36 , L-69]
(1975)] and is said to belong to the chiral smectic C (hereinafter abbreviated as S C * ) phase or the chiral smectic H (hereinafter abbreviated as S H * ) phase based on the molecular arrangement. There is. Until now, the compounds shown in Table 1 are known as ferroelectric liquid crystal compounds [Ph. Martino Lager (Ph.
Lagarde), Zurnal de Fuisique (J.
Physique, 37 , C3-129 (1976)].
【表】【table】
本発明の目的は、水分及び光に対して安定な液
晶性化合物及び該液晶性化合物を含む液晶組成物
を提供することにある。
〔発明の概要〕
すなわち、本発明を概説すれば、本発明の第１
の発明は、液晶性化合物の発明であつて、一般式
：
（式中、Ｒは炭素数が20以下のアルキル基若し
くはアルコキシ基であり、Ｒ*は炭素数が20以下
の光学活性なアルキル基で不斉炭素原子を含むも
のである。また、ｍ、ｎは自然数である。ただ
し、ｍ＝ｎ＝１のときＲは炭素数７以上であ
る。）で示されることを特徴とする。
そして、本発明の第２の発明は、液晶組成物の
発明であつて、少なくとも２種の液晶成分からな
り、そのうち、少なくとも１種は上記一般式で
示される液晶性化合物を含むことを特徴とする。
前述したように、強誘電性液晶相はＳC *相若
しくはＳH *相に属すが、これら２つの液晶相の
特徴は、分子が層を形成して配列しており、その
層の面において分子が特定の方向に傾斜して並
び、かつ傾斜方向が層と層との間で少しずつずれ
て全体としてら旋構造を持つことにある〔R.B.
メイヤー（R.B.Meyer）、モレキユラー クリス
タルズ アンド リキツド クリスタルズ（Mol.
Cryst.Liq.Cryst.），40，33（1977）〕。自発分極
はこのら旋軸（層面に対して垂直）に垂直な方向
を向いている。ところで、分子構造と強誘電性発
現の関係を詳細に検討した結果、このような液晶
相の分子配列と自発分極を誘起させるためには、
分子構造として次の２点が必要であることが判明
した。すなわち、ら旋構造を誘起するための光学
活性基を分子末端に持つことと、自発分極を誘起
させるために液晶分子長軸に対してほぼ垂直方向
に双極子を有する置換基を分子末端部分に有する
ことである。したがつて、既存強誘電性液晶性化
合物にみられるアゾメチン結合（−CH＝Ｎ−）
やベンゼン環とエステル結合
An object of the present invention is to provide a liquid crystal compound that is stable against moisture and light, and a liquid crystal composition containing the liquid crystal compound. [Summary of the Invention] That is, if the present invention is summarized, the first aspect of the present invention is as follows.
The invention is an invention of a liquid crystal compound, which has the general formula: (In the formula, R is an alkyl group or an alkoxy group having 20 or less carbon atoms, and R * is an optically active alkyl group having 20 or less carbon atoms and contains an asymmetric carbon atom. In addition, m and n are natural numbers. (However, when m=n=1, R has 7 or more carbon atoms.) A second invention of the present invention is an invention of a liquid crystal composition, characterized in that it is composed of at least two kinds of liquid crystal components, and at least one of them contains a liquid crystal compound represented by the above general formula. do. As mentioned above, the ferroelectric liquid crystal phase belongs to the S C * phase or the S H * phase, but the characteristics of these two liquid crystal phases are that the molecules are arranged to form a layer, and the plane of the layer is The reason is that the molecules are aligned in a specific direction, and the direction of the inclination is slightly shifted from layer to layer, creating a spiral structure as a whole [RB
RBMeyer, Molecular Crystals and Liquid Crystals (Mol.
Cryst.Liq.Cryst.), 40 , 33 (1977)]. Spontaneous polarization points in a direction perpendicular to this helical axis (perpendicular to the layer plane). By the way, as a result of a detailed study of the relationship between molecular structure and ferroelectricity development, we found that in order to induce such molecular alignment and spontaneous polarization of the liquid crystal phase,
It has been found that the following two points are necessary for the molecular structure. In other words, it is necessary to have an optically active group at the end of the molecule to induce a helical structure, and a substituent having a dipole in a direction almost perpendicular to the long axis of the liquid crystal molecule at the end of the molecule to induce spontaneous polarization. It is to have. Therefore, the azomethine bond (-CH=N-) found in existing ferroelectric liquid crystal compounds
or benzene ring and ester bond
以下、本発明を実施例により、更に詳細に説明
するが、本発明はこれらに限定されない。
なお以下の説明において相転移温度の値は測定
方法や純度により若干の変動を伴うものである。
実施例 １
ｐ―ｎ―デシルオキシ安息香酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル
の合成
ｐ―ヒドロキシ安息香酸690ｇ、（−）２―メチ
ルブタノール650ｇ、ベンゼン3l、濃硫酸30ml
を、デイーン・スターク型還流冷却器を付けて加
熱かくはんし、生成する水を除去した。約11時間
還流後、冷却し、氷水を加えて硫酸を除く。反応
母液を炭酸ナトリウム水溶液、水で洗浄した後、
ベンゼンを留去して油状のｐ―ヒドロキシ安息香
酸２―メチルブチルエステルを得た。
ｐ―ｎ―デシルオキシ安息香酸13.9ｇを過剰の
塩化チオニルと共に還流下に１時間加熱した後、
未反応の塩化チオニルを留去してｐ―ｎ―デシル
オキシ安息香酸塩化物を得た。先に合成したｐ―
ヒドロキシ安息香酸―２―メチルブチルエステル
10.6ｇをピリジン40mlに溶解し、冷却したところ
へ、前記ｐ―ｎ―デシルオキシ安息香酸塩化物の
トルエン溶液をかくはん下に加え、80℃で２時間
反応を行つた。次いで、氷と6N塩酸を加えて酸
性にし、有機層を水、2N水酸化ナトリウム水溶
液、水の順に洗浄した後、溶媒を留去した。残留
物をエタノールより２回再結晶してｐ―ｎ―デシ
ルオキシ安息香酸―p′―（２―メチルブトキシカ
ルボニル）フエニルエステルを得た。
元素分析値C29H40O5として
計算値 分析値
Ｃ 74.32％ 74.2％
Ｈ 8.60％ 8.6％
比旋光度〔α〕２３℃Ｄ＝＋2.4゜（クロロホルム溶
液）
実施例 ２
実施例１と同様の合成方法により一般式にお
いてＲ（アルキル基若しくはアルコキシ基）が実
施例１と異なる以下の各化合物を合成することが
できる。(1)ｐ―ｎ―ヘプチルオキシ安息香酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、(2)ｐ―ｎ―オクチルオキシ安息香酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、(3)ｐ―ｎ―ノニルオキシ安息香酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、(4)ｐ―ｎ―ウンデシルオキシ安息香酸
―p′―（２―メチルブトキシカルボニル）フエニ
ルエステル、(5)ｐ―ｎ―ドデシルオキシ安息香酸
―p′―（２―メチルブトキシカルボニル）フエニ
ルエステル、(6)ｐ―ｎ―トリデシルオキシ安息香
酸―p′―（２―メチルブトキシカルボニル）フエ
ニルエステル、(7)ｐ―ｎ―テトラデシルオキシ安
息香酸―p′―（２―メチルブトキシカルボニル）
フエニルエステル、(8)ｐ―ｎ―ペンタデシルオキ
シ安息香酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、(9)ｐ―ｎ―ヘキサデシル
オキシ安息香酸―p′―（２―メチルブトキシカル
ボニル）フエニルエステル、(10)ｐ―ｎ―ヘプタデ
シルオキシ安息香酸―p′―（２―メチルブトキシ
カルボニル）フエニルエステル、(11)ｐ―ｎ―オク
タデシルオキシ安息香酸―p′―（２―メチルブト
キシカルボニル）フエニルエステル、(12)ｐ―ｎ―
デシルオキシ安息香酸―p′―（１―メチルヘプト
キシカルボニル）フエニルエステル、（13）ｐ―
ｎ―ドデシルオキシ安息香酸―p′―（１―メチル
ヘプトキシカルボニル）フエニルエステル、
（14）ｐ―ｎ―ヘプチル安息香酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、
（15）ｐ―ｎ―オクチル安息香酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、
（16）ｐ―ｎ―ノニル安息香酸―p′―（２―メチ
ルブトキシカルボニル）フエニルエステル、
（17）ｐ―ｎ―デシル安息香酸―p′―（２―メチ
ルブトキシカルボニル）フエニルエステル、
（18）ｐ―ｎ―ウンデシル安息香酸―p′―（２―
メチルブトキシカルボニル）フエニルエステル、
（19）ｐ―ｎ―ドデシル安息香酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、
（20）ｐ―ｎ―トリデシル安息香酸―p′―（２―
メチルブトキシカルボニル）フエニルエステル、
（21）ｐ―ｎ―テトラデシル安息香酸―p′―（２
―メチルブトキシカルボニル）フエニルエステ
ル、（22）ｐ―ｎ―ペンタデシル安息香酸―p′―
（２―メチルブトキシカルボニル）フエニルエス
テル、（23）ｐ―ｎ―ヘキサデシル安息香酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、（24）ｐ―ｎ―ヘプタデシル安息香酸
―p′―（２―メチルブトキシカルボニル）フエニ
ルエステル、（25）ｐ―ｎ―オクタデシル安息香
酸―p′―（２―メチルブトキシカルボニル）フエ
ニルエステル、（26）ｐ―ｎ―ノナデシル安息香
酸―p′―（２―メチルブトキシカルボニル）フエ
ニルエステル、（27）ｐ―ｎ―エイコシル安息香
酸―p′―（２―メチルブトキシカルボニル）フエ
ニルエステル。
表２に実施例１、実施例２で製造したｐ―ｎ―
アルコキシ安息香酸―p′―（２―メチルブトキシ
カルボニル）フエニルエステルの相転移温度を示
す。表２中に示すように、これらの化合物はアル
キル基の炭素数が７以上のものでモノトロピツク
なＳ＊ Ｃ相が観測された。なお、略号は表１と同じ
である。
EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto. In the following explanation, the value of phase transition temperature is subject to slight variations depending on the measurement method and purity. Example 1 p-n-decyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester Synthesis of p-hydroxybenzoic acid 690g, (-)2-methylbutanol 650g, benzene 3l, concentrated sulfuric acid 30ml
was heated and stirred using a Dean-Stark reflux condenser to remove the water produced. After refluxing for about 11 hours, cool and add ice water to remove sulfuric acid. After washing the reaction mother liquor with an aqueous sodium carbonate solution and water,
Benzene was distilled off to obtain oily p-hydroxybenzoic acid 2-methylbutyl ester. After heating 13.9 g of pn-decyloxybenzoic acid with excess thionyl chloride under reflux for 1 hour,
Unreacted thionyl chloride was distilled off to obtain pn-decyloxybenzoic acid chloride. The previously synthesized p-
Hydroxybenzoic acid-2-methylbutyl ester
10.6 g was dissolved in 40 ml of pyridine and cooled. The toluene solution of the p-n-decyloxybenzoic acid chloride was added with stirring, and the reaction was carried out at 80° C. for 2 hours. Next, ice and 6N hydrochloric acid were added to make the mixture acidic, and the organic layer was washed successively with water, a 2N aqueous sodium hydroxide solution, and water, and then the solvent was distilled off. The residue was recrystallized twice from ethanol to obtain p-n-decyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester. Elemental analysis value C 29 H 40 O 5 Calculated value Analytical value C 74.32% 74.2% H 8.60% 8.6% Specific rotation [α] 23 °C D = +2.4° (chloroform solution) Example 2 Same as Example 1 The following compounds in which R (alkyl group or alkoxy group) in the general formula is different from that in Example 1 can be synthesized by the synthesis method. (1) p-n-heptyloxybenzoic acid
p'-(2-methylbutoxycarbonyl) phenyl ester, (2)p-n-octyloxybenzoic acid-
p′-(2-methylbutoxycarbonyl)phenyl ester, (3)p-n-nonyloxybenzoic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (4) p-n-undecyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (5) p-n-dodecyloxy Benzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (6) p-n-tridecyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (7) p-n -Tetradecyloxybenzoic acid-p'-(2-methylbutoxycarbonyl)
Phenyl ester, (8) p-n-pentadecyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (9) p-n-hexadecyloxybenzoic acid-p'-(2- methylbutoxycarbonyl) phenyl ester, (10) p-n-heptadecyloxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (11) p-n-octadecyloxybenzoic acid-p'- (2-methylbutoxycarbonyl) phenyl ester, (12)pn-
Decyloxybenzoic acid p'-(1-methylheptoxycarbonyl) phenyl ester, (13) p-
n-dodecyloxybenzoic acid-p'-(1-methylheptoxycarbonyl) phenyl ester,
(14) p-n-heptylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(15) p-n-octylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(16) p-n-nonylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(17) p-n-decylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(18) p-n-undecylbenzoic acid-p'-(2-
methylbutoxycarbonyl) phenyl ester,
(19) p-n-dodecylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(20) p-n-tridecylbenzoic acid-p′-(2-
methylbutoxycarbonyl) phenyl ester,
(21) p-n-tetradecylbenzoic acid-p′-(2
-methylbutoxycarbonyl) phenyl ester, (22) p-n-pentadecylbenzoic acid -p'-
(2-methylbutoxycarbonyl) phenyl ester, (23) p-n-hexadecylbenzoic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (24) p-n-heptadecylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (25) p-n-octadecylbenzoic acid- p'-(2-methylbutoxycarbonyl) phenyl ester, (26) p-n-nonadecylbenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (27) p-n-eicosylbenzoic acid- p'-(2-methylbutoxycarbonyl) phenyl ester. Table 2 shows the p-n- produced in Example 1 and Example 2.
The phase transition temperature of alkoxybenzoic acid-p'-(2-methylbutoxycarbonyl) phenyl ester is shown. As shown in Table 2, monotropic S * C phase was observed in these compounds in which the alkyl group had 7 or more carbon atoms. Note that the abbreviations are the same as in Table 1.
【表】【table】
【表】
実施例 ３
４―ｎ―ヘプチルオキシ―4′―ビフエニルカル
ボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル
の合成
４―ｎ―ヘプチルオキシ―4′―ビフエニルカル
ボン酸10ｇと過剰の塩化チオニル50mlを還流下で
３時間加熱した後、未反応の塩化チオニルを留去
して４―ヘプチルオキシ―4′―ビフエニルカルボ
ン酸塩化物を得た。
実施例１に記載したｐ―ヒドロキシ安息香酸―
２―メチルブチルエステル7.2ｇを40mlのピリジ
ンに溶解したものに、上記の酸塩化物のトルエン
溶液を滴下する。以下実施例１と同様に処理して
粗生成物を得た。これをトルエンに溶解し、活性
アルミナのクロマトグラムカラムを通して副生成
物を除去し、更に酢酸エチルより２回再結晶して
４―ｎ―ヘプチルオキシ―4′―ビフエニルカルボ
ン酸―p′―（２―メチルブトキシカルボニル）フ
エニルエステルを得た。
元素分析値C32H38O5として
計算値 分析値
Ｃ 76.46％ 76.4％
Ｈ 7.62％ 7.7％
比旋光度〔α〕２３℃Ｄ＝＋2.8゜（クロロホルム溶
液）
実施例 ４
実施例３と同様の合成方法により一般式にお
いてＲ（アルキル基若しくはアルコキシ基）が実
施例３と異なる以下の各化合物を合成することが
できる。
(1)４―メトキシ―4′―ビフエニルカルボン酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、(2)４―エトキシ―4′―ビフエニルカル
ボン酸―p′―（２―メチルブトキシカルボニル）
フエニルエステル、(3)４―ｎ―プロポキシ―4′―
ビフエニルカルボン酸―p′―（２―メチルブトキ
シカルボニル）フエニルエステル、(4)４―ｎ―ブ
トキシ―4′―ビフエニルカルボン酸―p′―（２―
メチルブトキシカルボニル）フエニルエステル、
(5)４―ｎ―ペンチルオキシ―4′―ビフエニルカル
ボン酸―p′―（２―メチルブトキシカルボニル）
フエニルエステル、(6)４―ｎ―ヘキシルオキシ―
4′―ビフエニルカルボン酸―p′―（２―メチルブ
トキシカルボニル）フエニルエステル、(7)４―ｎ
―オクチルオキシ―4′―ビフエニルカルボン酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、(8)４―ｎ―ノニルオキシ―4′―ビフエ
ニルカルボン酸―p′―（２―メチルブトキシカル
ボニル）フエニルエステル、(9)４―ｎ―デシルオ
キシ―4′―ビフエニルカルボン酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、(10)
４―ｎ―ウンデシルオキシ―4′―ビフエニルカル
ボン酸―p′―（２―メチルブトキシカルボニル）
フエニルエステル、(11)４―ｎ―ドデシルオキシ―
4′―ビフエニルカルボン酸―p′―（２―メチルブ
トキシカルボニル）フエニルエステル、(12)４―ｎ
―トリデシルオキシ―4′―ビフエニルカルボン酸
―p′―（２―メチルブトキシカルボニル）フエニ
ルエステル、（13）４―ｎ―テトラデシルオキシ
―4′―ビフエニルカルボン酸―p′―（２―メチル
ブトキシカルボニル）フエニルエステル、（14）
４―ｎ―ペンタデシルオキシ―4′―ビフエニルカ
ルボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、（15）４―ｎ―ヘキサデ
シルオキシ―4′―ビフエニルカルボン酸―p′―
（２―メチルブトキシカルボニル）フエニルエス
テル、（16）４―ｎ―ヘプチルオキシ―4′―ビフ
エニルカルボン酸―p′―（２―メチルヘプトキシ
カルボニル）フエニルエステル、（17）４―ｎ―
オクチルオキシ―4′―ビフエニルカルボン酸―
p′―（１―メチルヘプトキシカルボニル）フエニ
ルエステル、（18）４―ｎ―ノナデシルオキシ―
4′―ビフエニルカルボン酸―p′―（２―メチルブ
トキシカルボニル）フエニルエステル、（19）４
―ｎ―エイコシルオキシ―4′―ビフエニルカルボ
ン酸―p′―（２―メチルブトキシカルボニル）フ
エニルエステル、（20）４―メチル―4′―ビフエ
ニルカルボン酸―p′―（２―メチルブトキシカル
ボニル）フエニルエステル、（21）４―エチル―
4′―ビフエニルカルボン酸―p′―（２―メチルブ
トキシカルボニル）フエニルエステル、（22）４
―ｎ―プロピル―4′―ビフエニルカルボン酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、（23）４―ｎ―ブチル―4′―ビフエニ
ルカルボン酸―p′―（２―メチルブトキシカルボ
ニル）フエニルエステル、（24）４―ｎ―ペンチ
ル―4′―ビフエニルカルボン酸―p′―（２―メチ
ルブトキシカルボニル）フエニルエステル、
（25）４―ｎ―ヘキシル―4′―ビフエニルカルボ
ン酸―p′―（２―メチルブトキシカルボニル）フ
エニルエステル、（26）４―ｎ―ヘプチル―4′―
ビフエニルカルボン酸―p′―（２―メチルブトキ
シカルボニル）フエニルエステル、（27）４―ｎ
―オクチル―4′―ビフエニルカルボン酸―p′―
（２―メチルブトキシカルボニル）フエニルエス
テル、（28）４―ｎ―ノニル―4′―ビフエニルカ
ルボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、（29）４―ｎ―デシル―
4′―ビフエニルカルボン酸―p′―（２―メチルブ
トキシカルボニル）フエニルエステル、（30）４
―ｎ―ウンデシル―4′―ビフエニルカルボン酸―
p′―（２―メチルブトキシカルボニル）フエニル
エステル、（31）４―ｎ―ドデシル―4′―ビフエ
ニルカルボン酸―p′―（２―メチルブトキシカル
ボニル）フエニルエステル、（32）４―ｎ―トリ
デシル―4′―ビフエニルカルボン酸―p′―（２―
メチルブトキシカルボニル）フエニルエステル、
（33）４―ｎ―テトラデシル―4′―ビフエニルカ
ルボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、（34）４―ｎ―ペンタデ
シル―4′―ビフエニルカルボン酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、
（35）４―ｎ―ヘキサデシル―4′―ビフエニルカ
ルボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、（36）４―ｎ―ヘプタデ
シル―4′―ビフエニルカルボン酸―p′―（２―メ
チルブトキシカルボニル）フエニルエステル、
（37）４―ｎ―オクタデシル―4′―ビフエニルカ
ルボン酸―p′―（２―メチルブトキシカルボニ
ル）フエニルエステル、（38）４―ｎ―ノナデシ
ル―4′―ビフエニルカルボン酸―p′―（２―メチ
ルブトキシカルボニル）フエニルエステル、
（39）４―ｎ―エイコシル―4′―ビフエニルカル
ボン酸―p′―（２―メチルブトキシカルボニル）
フエニルエステル。
下記表３、表４に実施例３、実施例４で製造し
た４―ｎ―アルコキシ―4′―ビフエニルカルボン
酸―p′―（２―メチルブトキシカルボニル）フエ
ニルエステルと４―ｎ―アルキル―4′―ビフエニ
ルカルボン酸―p′―（２―メチルブトキシカルボ
ニル）フエニルエステルの相転移温度を示す。各
表中に示すように、これらはＢC *相を広い温度
範囲で示した。なお、略号はCh以外は表１と同
じである。また、Chは以下の各表で表３と同じ
である。[Table] Example 3 4-n-heptyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester Synthesis of 4-n-heptyloxy-4'-biphenylcarboxylic acid (10 g) and excess thionyl chloride (50 ml) were heated under reflux for 3 hours, and unreacted thionyl chloride was distilled off to give 4-heptyloxy-4'. -Biphenylcarboxylic acid chloride was obtained. p-hydroxybenzoic acid described in Example 1
The toluene solution of the above acid chloride is added dropwise to a solution of 7.2 g of 2-methylbutyl ester dissolved in 40 ml of pyridine. Thereafter, the same procedure as in Example 1 was carried out to obtain a crude product. This was dissolved in toluene, passed through an activated alumina chromatogram column to remove byproducts, and then recrystallized twice from ethyl acetate to produce 4-n-heptyloxy-4'-biphenylcarboxylic acid-p'-( 2-methylbutoxycarbonyl) phenyl ester was obtained. Elemental analysis value C 32 H 38 O 5 Calculated value Analysis value C 76.46% 76.4% H 7.62% 7.7% Specific optical rotation [α] 23 °C D = +2.8° (Chloroform solution) Example 4 Same as Example 3 The following compounds in which R (alkyl group or alkoxy group) in the general formula is different from that in Example 3 can be synthesized by the synthesis method. (1)4-Methoxy-4'-biphenylcarboxylic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (2)4-ethoxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl)
Phenyl ester, (3)4-n-propoxy-4'-
Biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (4)4-n-butoxy-4'-biphenylcarboxylic acid-p'-(2-
methylbutoxycarbonyl) phenyl ester,
(5)4-n-pentyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl)
Phenyl ester, (6)4-n-hexyloxy-
4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (7)4-n
-Octyloxy-4'-biphenylcarboxylic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (8)4-n-nonyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (9)4- n-decyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (10)
4-n-undecyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl)
Phenyl ester, (11)4-n-dodecyloxy-
4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (12)4-n
-Tridecyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (13) 4-n-tetradecyloxy-4'-biphenylcarboxylic acid-p'-( 2-methylbutoxycarbonyl) phenyl ester, (14)
4-n-pentadecyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (15) 4-n-hexadecyloxy-4'-biphenylcarboxylic acid-p ′-
(2-methylbutoxycarbonyl) phenyl ester, (16) 4-n-heptyloxy-4'-biphenylcarboxylic acid-p'-(2-methylheptoxycarbonyl) phenyl ester, (17) 4-n ―
Octyloxy-4'-biphenylcarboxylic acid-
p'-(1-methylheptoxycarbonyl) phenyl ester, (18) 4-n-nonadecyloxy-
4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (19) 4
-n-eicosyloxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (20) 4-methyl-4'-biphenylcarboxylic acid-p'-(2- methylbutoxycarbonyl) phenyl ester, (21) 4-ethyl-
4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (22) 4
-n-propyl-4'-biphenylcarboxylic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (23) 4-n-butyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (24) 4- n-pentyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester,
(25) 4-n-hexyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (26) 4-n-heptyl-4'-
Biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (27) 4-n
-Octyl-4'-biphenylcarboxylic acid-p'-
(2-methylbutoxycarbonyl) phenyl ester, (28) 4-n-nonyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (29) 4-n-decyl ―
4′-biphenylcarboxylic acid-p′-(2-methylbutoxycarbonyl) phenyl ester, (30)4
-n-undecyl-4'-biphenylcarboxylic acid-
p'-(2-methylbutoxycarbonyl) phenyl ester, (31) 4-n-dodecyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (32) 4- n-Tridecyl-4'-biphenylcarboxylic acid-p'-(2-
methylbutoxycarbonyl) phenyl ester,
(33) 4-n-tetradecyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (34) 4-n-pentadecyl-4'-biphenylcarboxylic acid-p' -(2-methylbutoxycarbonyl) phenyl ester,
(35) 4-n-hexadecyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (36) 4-n-heptadecyl-4'-biphenylcarboxylic acid-p' -(2-methylbutoxycarbonyl) phenyl ester,
(37) 4-n-octadecyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester, (38) 4-n-nonadecyl-4'-biphenylcarboxylic acid-p' -(2-methylbutoxycarbonyl) phenyl ester,
(39) 4-n-eicosyl-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl)
Phenyl ester. Tables 3 and 4 below show the 4-n-alkoxy-4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester and 4-n-alkyl produced in Example 3 and Example 4. The phase transition temperature of -4'-biphenylcarboxylic acid-p'-(2-methylbutoxycarbonyl) phenyl ester is shown. As shown in each table, these exhibited the B C * phase over a wide temperature range. Note that the abbreviations are the same as in Table 1 except for Ch. In addition, Ch is the same as in Table 3 in each table below.
【表】【table】
【表】【table】
【表】
実施例 ５
ｐ―ｎ―オクチル安息香酸―4′―（２―メチル
ブトキシカルボニル）―４―ビフエニリルエス
テル
の合成
４―ヒドロキシ―4′―ビフエニルカルボン酸20
ｇ、（−）２―メチルブタノール53ｇ、濃硫酸４
ｇを20分間還流させた後、ベンゼン500mlを加え
デイーン・スターク型還流冷却器を付けて加熱
し、生成した水を除去した。反応母液を冷却した
後で母液を水洗し、溶媒を留去して４―ヒドロキ
シ―4′―ビフエニルカルボン酸―２―メチルブチ
ルエステルの粗生成物を得た。これをベンゼン―
ヘプタン混合溶媒から再結晶して融点115〜116℃
の精製品を得た。
ｐ―ｎ―オクチル安息香酸７ｇと過剰の塩化チ
オニルとより合成したｐ―ｎ―オクチル安息香酸
塩化物をトルエンに溶解し、これを上記４―ヒド
ロキシ―4′―ビフエニルカルボン酸―２―メチル
ブチルエステル8.3ｇのピリジン溶液に加え、80
℃で３時間反応させた。以下実施例１と同様に処
理して粗生成物を得、これを酢酸エチルより２回
再結晶してｐ―ｎ―オクチル安息香酸―4′―（２
―メチルブトキシカルボニル）―４―ビフエニリ
ルエステルを得た。
元素分析C33H40O4として
計算値 分析値
Ｃ 79.16％ 79.1％
Ｈ 8.05％ 8.1％
比旋光度〔α〕２３℃Ｄ＝＋2.5゜（クロロホルム溶
液）
実施例 ６
実施例５と同様の合成方法により一般式にお
いてＲ（アルキル基若しくはアルコキシ基）が実
施例５と異なる以下の各化合物を合成することが
できる。
(1)ｐ―メトキシ安息香酸―4′―（２―メチルブ
トキシカルボニル）―４―ビフエニリルエステ
ル、(2)ｐ―エトキシ安息香酸―4′―（２―メチル
ブトキシカルボニル）―４―ビフエニリルエステ
ル、(3)ｐ―ｎ―プロポキシ安息香酸―4′―（２―
メチルブトキシカルボニル）―４―ビフエニリル
エステル、(4)ｐ―ｎ―ブトキシ安息香酸―4′―
（２―メチルブトキシカルボニル）―４―ビフエ
ニリルエステル、(5)ｐ―ｎ―ペンチルオキシ安息
香酸―4′―（２―メチルブトキシカルボニル）―
４―ビフエニリルエステル、(6)ｐ―ｎ―ヘキシル
オキシ安息香酸―4′―（２―メチルブトキシカル
ボニル）―４―ビフエニリルエステル、(7)ｐ―ｎ
―ヘプチルオキシ安息香酸―4′―（２―メチルブ
トキシカルボニル）―４―ビフエニリルエステ
ル、(8)ｐ―ｎ―オクチルオキシ安息香酸―4′―
（２―メチルブトキシカルボニル）―４―ビフエ
ニリルエステル、(9)ｐ―ｎ―ノニルオキシ安息香
酸―4′―（２―メチルブトキシカルボニル）―４
―ビフエニリルエステル、(10)ｐ―ｎ―デシルオキ
シ安息香酸―4′―（２―メチルブトキシカルボニ
ル）―４―ビフエニリルエステル、(11)ｐ―ｎ―ウ
ンデシルオキシ安息香酸―4′―（２―メチルブト
キシカルボニル）―４―ビフエニリルエステル、
(12)ｐ―ｎ―ドデシルオキシ安息香酸―4′―（２―
メチルブトキシカルボニル）―４―ビフエニリル
エステル、（13）ｐ―ｎ―トリデシルオキシ安息
香酸―4′―（２―メチルブトキシカルボニル）―
４―ビフエニリルエステル、（14）ｐ―ｎ―テト
ラデシルオキシ安息香酸―4′―（２―メチルブト
キシカルボニル）―４―ビフエニリルエステル、
（15）ｐ―ｎ―ペンタデシルオキシ安息香酸―
4′―（２―メチルブトキシカルボニル）―４―ビ
フエニリルエステル、（16）ｐ―ｎ―ヘキサデシ
ルオキシ安息香酸―4′―（２―メチルブトキシカ
ルボニル）―４―ビフエニリルエステル、（17）
ｐ―ｎ―ヘプチルオキシ安息香酸―4′―（１―メ
チルプロポキシカルボニル）―４―ビフエニリル
エステル、（18）ｐ―ｎ―オクチルオキシ安息香
酸―4′―（１―メチルヘプチルオキシカルボニ
ル）―４―ビフエニリルエステル、（19）ｐ―ｎ
―ノナデシルオキシ安息香酸―4′―（２―メチル
ブトキシカルボニル）―４―ビフエニリルエステ
ル、（20）ｐ―ｎ―エイコシルオキシ安息香酸―
4′―（２―メチルブトキシカルボニル）―４―ビ
フエニリルエステル、（21）ｐ―メチル安息香酸
―4′―（２―メチルブトキシカルボニル）―４―
ビフエニリルエステル、（22）ｐ―エチル安息香
酸―4′―（２―メチルブトキシカルボニル）―４
―ビフエニリルエステル、（23）ｐ―ｎ―プロピ
ル安息香酸―4′―（２―メチルブトキシカルボニ
ル）―４―ビフエニリルエステル、（24）ｐ―ｎ
―ブチル安息香酸―4′―（２―メチルブトキシカ
ルボニル）―４―ビフエニリルエステル、（25）
ｐ―ｎ―ペンチル安息香酸―4′―（２―メチルブ
トキシカルボニル）―４―ビフエニリルエステ
ル、（26）ｐ―ｎ―ヘキシル安息香酸―4′（２―
メチルブトキシカルボニル）―４―ビフエニリル
エステル、（27）ｐ―ｎ―ヘプチル安息香酸―
4′―（２―メチルブトキシカルボニル）―４―ビ
フエニリルエステル、（28）ｐ―ｎ―ノニル安息
香酸―4′―（２―メチルブトキシカルボニル）―
４―ビフエニリルエステル、（29）ｐ―ｎ―デシ
ル安息香酸―4′―（２―メチルブトキシカルボニ
ル）―４―ビフエニリルエステル、（30）ｐ―ｎ
―ウンデシル安息香酸―4′―（２―メチルブトキ
シカルボニル）―４―ビフエニリルエステル、
（31）ｐ―ｎ―ドデシル安息香酸―4′―（２―メ
チルブトキシカルボニル）―４―ビフエニリルエ
ステル、（32）ｐ―ｎ―トリデシル安息香酸―
4′―（２―メチルブトキシカルボニル）―４―ビ
フエニルエステル、（33）ｐ―ｎ―テトラデシル
安息香酸―4′―（２―メチルブトキシカルボニ
ル）―４―ビフエニリルエステル、（34）ｐ―ｎ
―ペンタデシル安息香酸―4′―（２―メチルブト
キシカルボニル）―４―ビフエニリルエステル、
（35）ｐ―ｎ―ヘキサデシル安息香酸―4′―（２
―メチルブトキシカルボニル）―４―ビフエニリ
ルエステル、（36）ｐ―ｎ―ヘプタデシル安息香
酸―4′―（２―メチルブトキシカルボニル）―４
―ビフエニリルエステル、（37）ｐ―ｎ―オクタ
デシル安息香酸―4′―（２―メチルブトキシカル
ボニル）―４―ビフエニリルエステル、（38）ｐ
―ｎ―ノナデシル安息香酸―4′―（２―メチルブ
トキシカルボニル）―４―ビフエニリルエステ
ル、（39）ｐ―エイコシル安息香酸―4′―（２―
メチルブトキシカルボニル）―４―ビフエニリル
エステル。
下記表５、表６に実施例５、実施例６で製造し
たｐ―ｎ―アルコキシ安息香酸―4′―（２―メチ
ルブトキシカルボニル）―４―ビフエニリルエス
テルとｐ―ｎ―アルキル安息香酸―4′―（２―メ
チルブトキシカルボニル）―４―ビフエニリルエ
ステルの相転移温度を示す。各表中に示すように
これらはＳC *相を示した。なお、略号は表３と
同義である。[Table] Example 5 p-n-octylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester Synthesis of 4-hydroxy-4'-biphenylcarboxylic acid 20
g, (-)2-methylbutanol 53 g, concentrated sulfuric acid 4
After refluxing for 20 minutes, 500 ml of benzene was added and heated with a Dean-Stark reflux condenser to remove the water produced. After cooling the reaction mother liquor, the mother liquor was washed with water and the solvent was distilled off to obtain a crude product of 4-hydroxy-4'-biphenylcarboxylic acid-2-methylbutyl ester. This is benzene-
Recrystallized from heptane mixed solvent, melting point 115-116℃
A refined product was obtained. P-n-octylbenzoic acid chloride synthesized from 7 g of p-n-octylbenzoic acid and excess thionyl chloride was dissolved in toluene, and this was dissolved in the above-mentioned 2-methyl 4-hydroxy-4'-biphenylcarboxylate. Add to a solution of 8.3 g of butyl ester in pyridine, add 80
The reaction was carried out at ℃ for 3 hours. Thereafter, the same treatment as in Example 1 was carried out to obtain a crude product, which was recrystallized twice from ethyl acetate to p-n-octylbenzoic acid-4'-(2
-methylbutoxycarbonyl)-4-biphenylyl ester was obtained. Elemental analysis C 33 H 40 O 4 Calculated value Analytical value C 79.16% 79.1% H 8.05% 8.1% Specific rotation [α] 23 °C D = +2.5° (Chloroform solution) Example 6 Same as Example 5 Depending on the synthesis method, the following compounds in which R (alkyl group or alkoxy group) in the general formula is different from Example 5 can be synthesized. (1) p-methoxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (2) p-ethoxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester enylyl ester, (3)p-n-propoxybenzoic acid-4'-(2-
methylbutoxycarbonyl)-4-biphenylyl ester, (4) p-n-butoxybenzoic acid-4'-
(2-methylbutoxycarbonyl)-4-biphenylyl ester, (5)p-n-pentyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-
4-biphenylyl ester, (6) p-n-hexyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (7) p-n
-Heptyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (8)p-n-octyloxybenzoic acid-4'-
(2-methylbutoxycarbonyl)-4-biphenylyl ester, (9)p-n-nonyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4
-biphenylyl ester, (10) p-n-decyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (11) p-n-undecyloxybenzoic acid-4' -(2-methylbutoxycarbonyl)-4-biphenylyl ester,
(12)p-n-dodecyloxybenzoic acid-4'-(2-
(methylbutoxycarbonyl)-4-biphenylyl ester, (13) p-n-tridecyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-
4-biphenylyl ester, (14) p-n-tetradecyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester,
(15) pn-pentadecyloxybenzoic acid
4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (16) p-n-hexadecyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, ( 17)
p-n-heptyloxybenzoic acid-4'-(1-methylpropoxycarbonyl)-4-biphenylyl ester, (18) p-n-octyloxybenzoic acid-4'-(1-methylheptyloxycarbonyl) -4-biphenylyl ester, (19)p-n
-Nonadecyloxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (20) p-n-eicosyloxybenzoic acid-
4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (21) p-methylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-
Biphenylyl ester, (22) p-ethylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4
-biphenylyl ester, (23) p-n-propylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (24) p-n
-Butylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (25)
p-n-pentylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (26) p-n-hexylbenzoic acid-4'(2-
methylbutoxycarbonyl)-4-biphenylyl ester, (27) p-n-heptylbenzoic acid-
4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (28) p-n-nonylbenzoic acid-4'-(2-methylbutoxycarbonyl)-
4-biphenylyl ester, (29) p-n-decylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (30) p-n
-Undecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester,
(31) p-n-dodecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (32) p-n-tridecylbenzoic acid-
4'-(2-methylbutoxycarbonyl)-4-biphenyl ester, (33) p-n-tetradecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenyl ester, (34) p -n
-pentadecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester,
(35) p-n-hexadecylbenzoic acid-4'-(2
-methylbutoxycarbonyl)-4-biphenylyl ester, (36) p-n-heptadecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4
-biphenylyl ester, (37) p-n-octadecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (38) p
-n-nonadecylbenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, (39) p-eicosylbenzoic acid-4'-(2-
methylbutoxycarbonyl)-4-biphenylyl ester. Tables 5 and 6 below show p-n-alkoxybenzoic acid-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester and p-n-alkylbenzoic acid produced in Example 5 and Example 6. The phase transition temperature of -4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester is shown. As shown in each table, these exhibited S C * phase. Note that the abbreviations have the same meanings as in Table 3.
【表】【table】
【表】
また、他の光学活性アルコールを用い、同様な
合成方法により一般式，，に係わる化合物
として下記表７に示すものを得た。該化合物の相
転移温度を示す。なお、略号は表３と同義であ
る。[Table] In addition, the compounds shown in Table 7 below were obtained as compounds related to the general formula, by using other optically active alcohols and using similar synthetic methods. The phase transition temperature of the compound is shown. Note that the abbreviations have the same meanings as in Table 3.
【表】【table】
以上説明したように、本発明の液晶性化合物及
び液晶組成物は、強誘電性液晶相を示し、しかも
安定な分子構造であり、既存の強誘電性液晶化合
物にみられない水分や光に対する安定性を持つと
いう格別顕著な効果をもつている。
As explained above, the liquid crystal compound and liquid crystal composition of the present invention exhibit a ferroelectric liquid crystal phase, have a stable molecular structure, and are stable against moisture and light, which is not seen in existing ferroelectric liquid crystal compounds. It has a particularly remarkable effect of having a sexual nature.
第１図は、本発明の応用例の液晶表示素子の応
答波形を示すグラフである。
FIG. 1 is a graph showing a response waveform of a liquid crystal display element according to an applied example of the present invention.
Claims (1)
くはアルコキシ基であり、Ｒ*は炭素数が20以下
の光学活性なアルキル基で不斉炭素原子を含むも
のである。また、ｍ、ｎは自然数である。ただ
し、ｍ＝ｎ＝１のときＲは炭素数７以上であ
る。）で示されることを特徴とする液晶性化合
物。 ２ 該式のＲ*が光学活性な２―メチルブチル
基である特許請求の範囲第１項記載の液晶性化合
物。 ３ 一般式の化合物が、下記一般式： （式中、Ｒは炭素数が７以上20以下のアルキル
基若しくはアルコキシ基である。）で示される特
許請求の範囲第１項記載の液晶性化合物。 ４ 一般式の化合物が、下記一般式： （式中、Ｒは炭素数が20以下のアルキル基若し
くはアルコキシ基である。）で示される特許請求
の範囲第１項記載の液晶性化合物。 ５ 一般式の化合物が、下記一般式： （式中、Ｒは炭素数が20以下のアルキル基若し
くはアルコキシ基である。）で示される特許請求
の範囲第１項記載の液晶性化合物。 ６ 少なくとも２種の液晶成分からなり、そのう
ち、少なくとも１種は一般式： （式中、Ｒは炭素数が20以下のアルキル基若し
くはアルコキシ基であり、Ｒ*は炭素数が20以下
の光学活性なアルキル基で不斉炭素原子を含むも
のである。また、ｍ、ｎは自然数である。ただ
し、ｍ＝ｎ＝１のときＲは炭素数７以上であ
る。）で示される液晶性化合物を含むことを特徴
とする液晶組成物。 ７ 該式のＲ*が光学活性な２―メチルブチル
基である特許請求の範囲第６項に記載の液晶組成
物。[Claims] 1. General formula: (In the formula, R is an alkyl group or alkoxy group having 20 or less carbon atoms, and R * is an optically active alkyl group having 20 or less carbon atoms and contains an asymmetric carbon atom. In addition, m and n are natural numbers. (However, when m=n=1, R has 7 or more carbon atoms.) 2. The liquid crystal compound according to claim 1, wherein R * in the formula is an optically active 2-methylbutyl group. 3 The compound of the general formula has the following general formula: (In the formula, R is an alkyl group or an alkoxy group having 7 or more and 20 or less carbon atoms.) 4 The compound of the general formula has the following general formula: (wherein R is an alkyl group or an alkoxy group having 20 or less carbon atoms) according to claim 1. 5 The compound of the general formula has the following general formula: (wherein R is an alkyl group or an alkoxy group having 20 or less carbon atoms) according to claim 1. 6 Consists of at least two types of liquid crystal components, at least one of which has the general formula: (In the formula, R is an alkyl group or alkoxy group having 20 or less carbon atoms, and R * is an optically active alkyl group having 20 or less carbon atoms and contains an asymmetric carbon atom. In addition, m and n are natural numbers. (However, when m=n=1, R has 7 or more carbon atoms.) A liquid crystal composition comprising a liquid crystal compound represented by the following. 7. The liquid crystal composition according to claim 6, wherein R * in the formula is an optically active 2-methylbutyl group.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13780083A JPS6032748A (en) | 1983-07-29 | 1983-07-29 | Liquid crystal compound |
| DE8383111666T DE3377219D1 (en) | 1982-11-26 | 1983-11-22 | Smectic liquid crystal compounds and liquid crystal compositions |
| EP83111666A EP0110299B2 (en) | 1982-11-26 | 1983-11-22 | Smectic liquid crystal compounds and liquid crystal compositions |
| KR1019830005596A KR920004141B1 (en) | 1982-11-26 | 1983-11-26 | Smectic liquid crystal composition |
| US06/555,617 US4576732A (en) | 1982-11-26 | 1983-11-28 | Ferroelectric liquid crystal compounds and liquid crystal compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13780083A JPS6032748A (en) | 1983-07-29 | 1983-07-29 | Liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032748A JPS6032748A (en) | 1985-02-19 |
| JPS6230981B2 true JPS6230981B2 (en) | 1987-07-06 |
Family
ID=15207140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13780083A Granted JPS6032748A (en) | 1982-11-26 | 1983-07-29 | Liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032748A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0678280B2 (en) * | 1985-04-26 | 1994-10-05 | 大日本インキ化学工業株式会社 | Ferroelectric compound and liquid crystal composition |
| JPH0699370B2 (en) * | 1985-04-04 | 1994-12-07 | 大日本インキ化学工業株式会社 | Compound having nitro group and liquid crystal composition |
| JPH0613702B2 (en) * | 1985-03-12 | 1994-02-23 | チッソ株式会社 | Chiral smectic liquid crystal composition |
| JPS61210056A (en) * | 1985-03-14 | 1986-09-18 | Chisso Corp | Halogen-containing optically active liquid crystal compound and liquid crystal composition |
| JP2531646B2 (en) * | 1986-10-16 | 1996-09-04 | キヤノン株式会社 | Liquid crystal composition and liquid crystal device using the same |
| US5098602A (en) * | 1988-05-11 | 1992-03-24 | Nippon Mining Co., Ltd. | Novel halogen-containing ester compounds, and their intermediates, and method of producing the same as well as liquid crystal compositions containing the same and light switching elements |
| EP0450595B1 (en) * | 1990-04-04 | 1995-03-01 | Mitsubishi Gas Chemical Company, Inc. | Liquid crystal compound and liquid crystal display device |
| US6217793B1 (en) | 1998-06-05 | 2001-04-17 | Mitsui Chemicals, Inc. | Acetylene compound, liquid crystal composition and liquid crystal element |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4965389A (en) * | 1972-10-25 | 1974-06-25 | ||
| JPS5920250A (en) * | 1982-07-27 | 1984-02-01 | Chisso Corp | Liquid crystal ester compound |
| JPS5929641A (en) * | 1982-08-13 | 1984-02-16 | Ube Ind Ltd | Preparation of benzoic acid phenyl ester |
-
1983
- 1983-07-29 JP JP13780083A patent/JPS6032748A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4965389A (en) * | 1972-10-25 | 1974-06-25 | ||
| JPS5920250A (en) * | 1982-07-27 | 1984-02-01 | Chisso Corp | Liquid crystal ester compound |
| JPS5929641A (en) * | 1982-08-13 | 1984-02-16 | Ube Ind Ltd | Preparation of benzoic acid phenyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6032748A (en) | 1985-02-19 |
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