CN1082992C - 可光致交联的液晶 - Google Patents
可光致交联的液晶 Download PDFInfo
- Publication number
- CN1082992C CN1082992C CN95103768A CN95103768A CN1082992C CN 1082992 C CN1082992 C CN 1082992C CN 95103768 A CN95103768 A CN 95103768A CN 95103768 A CN95103768 A CN 95103768A CN 1082992 C CN1082992 C CN 1082992C
- Authority
- CN
- China
- Prior art keywords
- bis
- phenylcarbonyloxy
- benzoate
- coo
- acryloyloxyhexyloxy
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 230000003287 optical effect Effects 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 8
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims abstract description 3
- -1 1, 4-phenylene, pyridine-2, 5-diyl Chemical group 0.000 claims description 289
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000004593 Epoxy Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 54
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- MNTKWYBPDFGVIV-UHFFFAOYSA-N 2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]benzoic acid Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)C(C(=O)O)=CC=1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 MNTKWYBPDFGVIV-UHFFFAOYSA-N 0.000 description 5
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 5
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- RLWWVISREOEANH-UHFFFAOYSA-N [3-formyl-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1C=O)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 RLWWVISREOEANH-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 3
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 description 2
- FLPSQLAEXYKMGQ-UHFFFAOYSA-N 4-(6-prop-2-enoyloxyhexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 FLPSQLAEXYKMGQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 150000002237 fumaric acid derivatives Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- NKULHAQAEBPFMZ-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-(11-prop-2-enoyloxyundecoxy)benzoyl]oxy]phenyl]decyl]-4-[4-(11-prop-2-enoyloxyundecoxy)benzoyl]oxyphenyl] 4-(11-prop-2-enoyloxyundecoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCCCOC(=O)C=C)C=C1 NKULHAQAEBPFMZ-UHFFFAOYSA-N 0.000 description 1
- MGCCQXJETORJMV-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]phenyl]decyl]-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 MGCCQXJETORJMV-UHFFFAOYSA-N 0.000 description 1
- SKGLMXGAQPBBMC-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-(7-prop-2-enoyloxyheptoxy)benzoyl]oxy]phenyl]decyl]-4-[4-(7-prop-2-enoyloxyheptoxy)benzoyl]oxyphenyl] 4-(7-prop-2-enoyloxyheptoxy)benzoate Chemical compound C1=CC(OCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCOC(=O)C=C)C=C1 SKGLMXGAQPBBMC-UHFFFAOYSA-N 0.000 description 1
- PNVUHRWPIFUFJE-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-(8-prop-2-enoyloxyoctoxy)benzoyl]oxy]phenyl]decyl]-4-[4-(8-prop-2-enoyloxyoctoxy)benzoyl]oxyphenyl] 4-(8-prop-2-enoyloxyoctoxy)benzoate Chemical compound C1=CC(OCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCOC(=O)C=C)C=C1 PNVUHRWPIFUFJE-UHFFFAOYSA-N 0.000 description 1
- LZXAAQGKJHHCDR-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-(9-prop-2-enoyloxynonoxy)benzoyl]oxy]phenyl]decyl]-4-[4-(9-prop-2-enoyloxynonoxy)benzoyl]oxyphenyl] 4-(9-prop-2-enoyloxynonoxy)benzoate Chemical compound C1=CC(OCCCCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCCCCOC(=O)C=C)C=C1 LZXAAQGKJHHCDR-UHFFFAOYSA-N 0.000 description 1
- LJKZHEWNQMOIGM-UHFFFAOYSA-N [3-[10-[2,5-bis[[4-[6-(2-methylprop-2-enoyloxy)hexoxy]benzoyl]oxy]phenyl]decyl]-4-[4-[6-(2-methylprop-2-enoyloxy)hexoxy]benzoyl]oxyphenyl] 4-[6-(2-methylprop-2-enoyloxy)hexoxy]benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C(=C)C)=CC=C1C(=O)OC(C=C1CCCCCCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCOC(=O)C(C)=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCOC(=O)C(C)=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C(C)=C)C=C1 LJKZHEWNQMOIGM-UHFFFAOYSA-N 0.000 description 1
- JZUPIYUMBFBOPG-UHFFFAOYSA-N [3-[6-[2,5-bis[[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxy]phenyl]hexyl]-4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxyphenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(OCCCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1CCCCCCC=2C(=CC=C(OC(=O)C=3C=CC(OCCCCCCOC(=O)C=C)=CC=3)C=2)OC(=O)C=2C=CC(OCCCCCCOC(=O)C=C)=CC=2)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 JZUPIYUMBFBOPG-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000758 substrate Substances 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
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
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Abstract
本发明涉及式I所示的可光致交联的液晶,含有这类化合物的液晶混合物以及它们以交联态在光学元件方面的应用。式I中,A表示可交联的介晶性残基;X表示单键、-COO-、-CH2O-、-CONH-或-C=N-;Q表示正亚烷基、环亚烷基、1,4-亚苯基、4,4′-亚联苯基或2,6-亚萘基。
Description
本发明涉及可光致交联的液晶、含有这类化合物的液晶混合物以及它们以交联态在光学元件方面的应用。
含有适量光引发剂的可光致交联的液晶可通过衬底(如玻璃或硅)上的取向层或在电场或磁场中取向,然后可通过用适当波长的光照射而交联。这样得到的取向即使在高温下仍可保持。当取向层由可光取向的聚合物网络层(PPN)构成时也可起取向作用,PPN通过用偏振的紫外光选择性辐射使液晶层上产生高分辨率取向图样。这类混杂层可以使聚合物薄层的光记录的高分辨率取向图案转印到任何厚度的双折射的密交联的聚合物层上。根据应用的需要使用可光致交联的液晶或可光致交联的液晶和小分子液晶和/或旋光活性(手性)添加剂的混合物。因此,可制造具有长期稳定性的光学元件(如光延迟器、波导器、光栅和滤光器、集成滤色器)、压电光学元件和具有非线性光学(NLO)性质等的光学元件。这类光学元件例如可用于投影系统。
其它性质(如双折射、折射率、透明性等)必须满足不同应用领域的不同要求。例如,光延迟器材料应具有较高的双折射,从而使集成光学元件的层厚度能够做得很小。
可光致交联的液晶除了常用于光学元件外,这类液晶材料还适用于光学数据传输用的包覆玻璃纤维。使用这类材料可提高纤维纵轴向的弹性模量、降低热膨胀系数并减小微变形损耗,从而提高了机械稳定性。
可光致交联的液晶必须具有良好的化学和热稳定性、在通用溶剂中的良好溶解性以及对于电场和电磁辐射的良好稳定性。另外,对于上述应用,其适宜的介晶相温度应为25-80℃,可能的话为25-100℃,例如,宽近晶型或向列型介晶相以及相应的手性近晶型和胆甾型介晶相。
因为液晶通常以几种组分的混合物的形式使用。各种组分间具有良好的混溶性这一点很重要。
A表示可交联的介晶性残基;
X表示单键、-COO-、-CH2O-、-CONH-或-C=N-;
Q表示正亚烷基、环亚烷基、1,4-亚苯基、4,4′-亚联苯基或2,6-亚萘基。
通式I化合物的特点是粘度较小。因此,可以容易地将它们涂布到适宜的表面上。这通常用旋转涂布法进行。另外,由于本发明的化合物具有液晶相,可在交联前施加电场对其进行定向。对于其中介晶性残基A各自表示通式II所示的残基的本发明的式I化合物尤为如此。其中,
环C和D各自独立地表示可任选被卤素、甲基和/或氰基取代的1,4-亚苯基、吡啶-2,5-二基、嘧啶-2,5-二基、反-1,4-亚环己基或反-1,3-二噁烷-2,5-二基;
Z1表示-CH2CH2-、-CH2O-、-COO-、-OOC-、-(CH2)4-或-(CH2)2O-;
Z2表示单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-、-OOC-、-(CH2)4-、-O(CH2)3-或-(CH2)3O-;
Z3表示-(CH2)m-、-(CH2)mO-、-O(CH2)m-、-(CH2)mCOO-、-OOC(CH2)m-、-(CH2)mOOC-或-COO(CH2)m-;
n为0或1;
m为1至16的整数;
R为可交联基团,如丙烯酸酯、甲基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、环氧基、衣康酸酯、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来酸衍生物、富马酸衍生物或肉桂酸衍生物,所述基团可任选被甲基、甲氧基、氰基和/或卤素取代。
特别优选的介晶性残基的化学结构中,环C和D各自独立地表示非取代的或氟取代的1,4-亚苯基、吡啶-2,5-二基、嘧啶-2,5-二基或反-1,4-亚环己基;Z1表示-CH2O-、-COO-或-OOC-;Z2表示-CH2CH2-、-CH2O-、-OCH2-、-COO-或-OOC-。
术语“正亚烷基”在本发明的范围内表示具有1至16个碳原子的直链亚烷基。特别优选的亚烷基为1,4-亚丁基、1,5-亚戊基、1,6-亚己基、1,7-亚庚基、1,8-亚辛基、1,9-亚壬基、1,10-亚癸基、1,11-亚十一烷基和1,12-亚十二烷基。术语“环亚烷基”表示具有4至8个碳原子的环状亚烷基,如1,3-亚环丁基、1,2-或1,3-亚环戊基、1,4-亚环己基、1,4-二环(2,2,2)辛烷二基等。
本发明中“可任选被卤素、甲基和/或氰基取代的1,4-亚苯基”包括1,4-亚苯基,氟、溴、氯、甲基或氰基取代的1,4-亚苯基,如2-或3-氟-1,4-亚苯基、1,3-二氟-1,4-亚苯基、2,6-或3,5-二氟-1,4-亚苯基、2-或3-氯-1,4-亚苯基、2,3-二氯-1,4-亚苯基、2,6-或3,5-二氯-1,4-亚苯基、2-或3-溴-1,4-亚苯基、2-或3-甲基-1,4-亚苯基、2-或3-氰基-1,4-亚苯基等。
丙烯酸酯、甲基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、丙烯酰亚苯基、丙烯酰胺、甲基丙烯酰胺、2-苯基丙烯酰胺、乙烯基醚、乙烯基酯、苯乙烯衍生物、马来酸衍生物、富马酸衍生物等是优选的残基R。在用式I化合物涂布适当的载体后,这些残基可用光化学方法交联。
特别优选的残基R是丙烯酸酯、甲基丙烯酸酯、丙烯酰氧基、甲基丙烯酰氧基、乙烯氧基和环氧基。
式I化合物中,X优选表示-COO-、-CONH-或-CH2O-基团。这些基团可由相应的醛容易地得到,然后与基团Q的适宜衍生物(Q优选表示-(CH2)p-(其中p为2~12的整数)或1,4-亚苯基)反应。
R1表示丙烯酸酯、甲基丙烯酸酯、2-氯丙烯酸酯、2-苯基丙烯酸酯、乙烯氧基或环氧基;
Z33表示-(CH2)m′-、-(CH2)m′O-、-(CH2)m′COO-或-(CH2)m′-OOC-;
m′为4至12的整数;
环C1表示可任选被卤素取代的1,4-亚苯基或反-1,4-亚环己基;
Z1表示-CH2CH2-、-CH2O-、-COO-、-OOC-、-(CH2)4-或-(CH2)3O-。
在每一步中混入少量BHT(2,6-二叔丁基-4-甲基苯酚/“丁基化羟基甲苯”)以阻止不需要的热交联。
式I化合物可以单一化合物的形式使用,或者互相混合使用和/或与其他液晶组分混合使用。
本发明的液晶混合物包含至少两种组分,其中至少一种组分是式I化合物。第二种组分和任何其它组分可以是其它的式I化合物或带有或不带有可光致交联的基团的其它已知液晶化合物。混合物中也可含有一种或多种手性组分。
考虑到式I化合物的良好溶解性和它们相互之间的良好混溶性,本发明的混合物中不同的式I化合物的含量可以很高,可高至100%(重量)。
下面用实施例更详细地说明本发明。在实施例中,C表示晶相、N表示向列相、S表示近晶相、I表示各向同性相。
实施例1
在室温、搅拌下,向0.7g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸和0.11g 1,4-二溴丁烷在20ml甲苯中的溶液中加入0.15g DBU(1,8-二氮杂二环[5,4,0]十一碳-1-烯(1,5-5)。将反应混合物在80℃下加热过夜,倾入100ml水中后,用乙酸乙酯萃取三次(每次用50ml)。合并的有机相用水(每次100ml)洗涤两次,用硫酸镁干燥,过滤并浓缩。用己烷-乙酸乙酯(体积比2∶1)将残余物在硅胶上进行色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用丙酮重结晶两次,得到0.3g 1,4-亚丁烯基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯];熔点(m.p.)(C-N)59℃,清亮点(cl.p.)(N-I)105℃。
用作原料的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸按下述方法制备:
(a)在0℃、搅拌下,于15分钟内向8.3g 2,5-二羟基苯甲醛、35.1g 4-[6-丙烯酰氧基己氧基]苯甲酸和0.1g 4-二甲氨基吡啶(DMAP)在600ml二氯甲烷中的溶液中加入29.7g N,N′-二环己基碳二亚胺(DCC)。将反应混合物在室温下搅拌过夜,然后过滤并浓缩。用己烷/乙酸乙酯(体积比1∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用乙醇重结晶两次,得到7.8g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛。
(b)向3,9g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛在50ml丙酮中的溶液中滴加18ml琼斯试剂。将混合物在室温下搅拌1小时,倾入100ml水中,然后用乙酸乙酯萃取三次(每次用50ml)。合并的有机相用水洗涤两次(每次用100ml),用硫酸镁干燥,过滤并浓缩。用叔丁基甲基醚在-78℃下将残余物重结晶,得到2.3g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸;m.p.(C-I)126℃;cl.p.(N-I)122℃。
可用类似方法制备下述化合物:
1,5-亚戊基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯];m.p.(C-N)62℃,cl.p.(N-I)96℃。
1,6-亚己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯];m.p.(C-N)94℃,cl.p.(N-I)113℃。
1,7-亚庚基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]:m.p.(C-N)45℃,cl.p.(N-I)85℃。
1,8-亚辛基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]:m.p.(C-N)65℃,cl.p.(N-I)97℃。
1,9-亚壬基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚丁基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,4-亚丁基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,4-亚丁基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,4-亚丁基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]。
1,4-亚丁基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2-氟-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2-氯-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2-溴-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2-氰基-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2,3-二氟-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2,3-二氯-4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2,3-二氯-4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(2,3-二氯-4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,5-亚戊基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,6-亚己基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,7-亚庚基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,8-亚辛基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,9-亚壬基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,10-亚癸基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
实施例2
(a)在0℃、搅拌下,于15分钟内向4.09g对苯二酚、35.1g2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸和0.1g4-二甲氨基吡啶在600ml二氯甲烷中的溶液中加入29.788g N,N′-二环己基碳二亚胺。将反应混合物在室温下搅拌过夜,然后过滤并浓缩。用己烷/乙酸乙酯(体积比1∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用乙醇重结晶两次,得到7.8g1,4-亚苯基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]。
可用类似方法制备下述化合物:
1,4-亚苯基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
反-1,4-亚环己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
反-1,4-亚环己基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
反-1,4-亚环己基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
反-1,4-亚环己基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
反-1,4-亚环己基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]。
反-1,4-亚环己基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
4,4′-亚联苯基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[7-甲基丙烯酰氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[8-甲基丙烯酰氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[9-甲基丙烯酰氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[10-甲基丙烯酰氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[11-甲基丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(2,3-二氯-4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[7-乙烯氧基庚氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[8-乙烯氧基辛氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[9-乙烯氧基壬氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[10-乙烯氧基癸氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[11-乙烯氧基十一烷氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(2,3-二氯-4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[6,7-环氧庚氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[7,8-环氧辛氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[8,9-环氧壬氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[9,10-环氧癸氧基]苯基羰氧基)苯甲酸酯]
1,4-亚苯基双[2,5-双(4-[10,11-环氧十一烷氧基]苯基羰氧基)苯甲酸酯]
实施例3
在室温、搅拌下,向0.7g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄醇和0.11g 1,4-二溴丁烷在20ml二甲亚砜中的溶液中加入0.15g叔丁醇钾。将反应混合物在室温下搅拌过夜,倾入100ml水中,然后用乙酸乙酯萃取三次(每次用50ml)。合并的有机相用水洗涤两次(每次用100ml),用硫酸镁干燥,过滤并浓缩。用己烷/乙酸乙酯(体积比2∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用丙酮重结晶两次,得到0.3g 1,4-亚丁基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]。
用作原料的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄醇用下述方法制备:
(a)在0℃下,用165ml水处理32g硼氢化钠和180ml乙醇的混合物,搅拌10分钟后,在0-5℃下滴加50g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛在100ml乙醇和10ml二氯甲烷中的溶液进行处理。将反应混合物在0℃下再搅拌30分钟,然后倾入100ml二氯甲烷中,用二氯甲烷萃取两次(每次用50ml)。合并的有机相用水洗涤两次(每次用100ml),用硫酸镁干燥,过滤并将滤液浓缩。残余物用叔丁基甲基醚重结晶,得到35g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基]苄醇。
可用类似方法制备下述化合物:
1,5-亚戊基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,4-亚丁基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苄基醚]
1,4-亚丁基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苄基醚]
1,4-亚丁基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苄基醚]
1,4-亚丁基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苄基醚]
1,4-亚丁基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苄基醚]
1,5-亚戊基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
1,6-亚己基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
1,7-亚庚基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
1,8-亚辛基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
1,9-亚壬基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
1,10-亚癸基双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苄基醚]
实施例4
在室温、搅拌下,向0.11g 1,4-二氨基丁烷在20ml二氯甲烷中的溶液中加入含0.7g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰氯和20ml二氯甲烷的溶液。将反应混合物在室温下搅拌过夜,倾入100ml水中,然后用乙酸乙酯萃取三次(每次用50ml)。合并的有机相用水洗涤两次(每次用100ml),用硫酸镁干燥,过滤并浓缩。用己烷/乙酸乙酯(体积比2∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用丙酮重结晶两次,得到0.3g 1,4-亚丁基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]。
用作原料的2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰氯用下述方法制备:
(a)将1.5g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸与25ml亚硫酰氯在100ml甲苯中于80℃下加热2小时。减压蒸发得到的溶液,残余物用20ml无水甲苯处理,再次减压蒸发溶液。残余物不经进一步纯化而直接用于下一步骤。
可用类似方法制备下述化合物:
1,5-亚戊基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酰胺]
1,4-亚丁基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,5-亚戊基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯甲酰胺]
1,4-亚丁基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,5-亚戊基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯甲酰胺]
1,4-亚丁基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,5-亚戊基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯甲酰胺]
1,4-亚丁基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,5-亚戊基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯甲酰胺]
1,4-亚丁基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,5-亚戊基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,6-亚己基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,7-亚庚基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,8-亚辛基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,9-亚壬基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]
1,10-亚癸基双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯甲酰胺]。
实施例5
(a)在0℃、搅拌下,于15分钟内向4.0g 1,5-双(对苯二酚基)戊烷、35.1g 4-[6-丙烯酰氧基己氧基]苯甲酸和0.1g4-二甲氨基吡啶在600ml二氯甲烷中的溶液中加入29.7g N,N′-二环己基碳二亚胺。将反应混合物在室温下搅拌过夜,然后过滤并浓缩。用己烷/乙酸乙酯(体积比1∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用乙醇重结晶两次,得到7.8g1,5-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)戊烷。
可用类似方法制备下述化合物:
1,6-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[7-丙烯酰氧基庚氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[8-丙烯酰氧基辛氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[9-丙烯酰氧基壬氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[10-丙烯酰氧基癸氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[11-丙烯酰氧基十一烷氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[6-甲基丙烯酰氧基己氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[6-乙烯氧基己氧基]苯基羰氧基)苯基]癸烷
1,6-双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯基]己烷
1,7-双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯基]庚烷
1,8-双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯基]辛烷
1,9-双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯基]壬烷
1,10-双[2,5-双(4-[5,6-环氧己氧基]苯基羰氧基)苯基]癸烷
实施例6
在搅拌和轻微回流下,向0.7g 2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲醛和0.15g 1,5-二氨基戊烷在20ml乙醇中的溶液中加入5滴冰醋酸。10分钟后浓缩反应混合物。用己烷/乙酸乙酯(体积比2∶1)将残余物在硅胶上用色谱法纯化,将用薄层色谱法鉴定为纯组分的级分用丙酮重结晶两次,得到0.3g 1,5-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]戊二胺。
可用类似方法制备下述化合物:
1,6-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]己二胺
1,7-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]庚二胺
1,8-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]辛二胺
1,9-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]壬二胺
1,10-双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)亚苄基]癸二胺
实施例7
将1,6-亚己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]用1%(重量)光引发剂(IRGACURE,CibaGeigy)和1%(重量)丁基化羟基甲苯(BHT)处理,溶于苯甲醚中(2%(重量)),然后以3500转/分的速度将其旋转涂布到已涂布PVA(PVA=聚乙烯醇)并经过磨擦的玻璃板上。将该层在加热块上于90℃下干燥,然后在真空炉中于90℃、真空下用氙光照射(例如3分钟)。得到层厚200μm、双折射(Δn)为0.15的平行取向的向列层。该层用作光延迟器。
实施例8
将1,6-亚己基双[2,5-双(4-[6-丙烯酰氧基己氧基]苯基羰氧基)苯甲酸酯]用1%(重量)IRGACURE,和1%(重量)BHT处理,溶于苯甲醚中(2%(重量)),然后以3500转/分的速度旋转涂布到玻璃板上。玻璃板上预先涂布有3-(E)-[4-氰基-4′-联苯基]丙烯酸甲基丙烯酰氧基乙酯并用线性偏振光照射。这样,通过该(PPN)层内的光刻掩蔽层光刻出预定的结构。将新层(在PPN层之上)在加热块上于90℃下干燥,在真空炉内于90℃下用氙光照射。所光刻的最初结构保持下来并原样由新的网络结构复制。可以观察到清楚的双折射(Δn)。该层用作结构光延迟器。
Claims (8)
1.通式I所示的化合物:其中,
X表示单键、-COO-、-CH2O-、-CONH-或-C=N-;
Q表示正亚烷基、环亚烷基、1,4-亚苯基、4,4’-亚联苯基或2,6-亚萘基;
环C和D各自独立地表示可任选被卤素、甲基和/或氰基取代的1,4-亚苯基、吡啶-2,5-二基、嘧啶-2,5-二基、反-1,4-亚环己基或反-1,3-二噁烷-2,5-二基;
Z1表示-CH2CH2-、-CH2O-、-COO-、-OOC-、-(CH2)4-或-(CH2)3O-;
Z2表示单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-、-OOC-、-(CH2)4-、-O(CH2)3-或-(CH2)3O-;
Z3表示-(CH2)m-、-(CH2)mO-、-O(CH2)m-、-(CH2)mCOO-、-OOC(CH2)m-、-(CH2)mOOC-或-COO(CH2)m-;
n为0或1;
m为1至16的整数;
R为丙烯酸酯、甲基丙烯酸酯、丙烯酰氧基、甲基丙烯酰氧基、乙烯氧基或环氧基。
2.根据权利要求1的化合物,其中介晶性残基A表示式II所示的残基:其中,
环C和D各自独立地表示无取代的或氟取代的亚苯基、吡啶-2,5-二基、嘧啶-2,5-二基或反-1,4-亚环己基;
Z1表示-CH2O-、-COO-或-OOC-;
Z2表示单键、-CH2CH2-、-CH2O-、-OCH2-、-COO-或-OOC-;
Z3、n和R的定义如权利要求1所述。
5.由至少两种组分组成的可交联的液晶混合物,其中至少一种组分是权利要求1所定义的式I化合物。
7.权利要求1-4中任一项所述的化合物以其交联态在光学元件方面的应用。
8.权利要求5或6所述的可交联液晶混合物以其交联态在光学元件方面的应用。
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CH95394 | 1994-03-30 |
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US (1) | US5567349A (zh) |
EP (1) | EP0675186B1 (zh) |
JP (1) | JP3866307B2 (zh) |
KR (1) | KR100388405B1 (zh) |
CN (1) | CN1082992C (zh) |
DE (1) | DE59504854D1 (zh) |
HK (1) | HK1011042A1 (zh) |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
DE69613962T2 (de) * | 1995-02-06 | 2002-04-04 | Merck Patent Gmbh | Direaktive mesogene verbindungen und zwischenprodukte |
US5707544A (en) * | 1995-06-07 | 1998-01-13 | Rolic Ag | Chromophore-containing photo cross-linkable liquid crystals |
DE59605841D1 (de) * | 1995-07-28 | 2000-10-12 | Rolic Ag Zug | Photovernetzbare Chirale Dotierstoffe |
DE59608943D1 (de) * | 1995-07-28 | 2002-05-02 | Rolic Ag Zug | Photovernetzbare flüssigkristalline 1,4-Dioxan-2,3-diyl-Derivate |
DE19714119A1 (de) | 1997-04-05 | 1998-10-08 | Daimler Benz Ag | Verbindungen, Verfahren zu deren Herstellung sowie Verfahren zur Herstellung flüssigkristalliner Polymere unter Verwendung dieser Verbindungen |
KR100566684B1 (ko) | 1997-05-22 | 2006-04-03 | 롤리크 아게 | 중합성 액정 화합물, 및 이를 포함하는 가교결합성 액정 혼합물 및 광학 부재 |
US6124970A (en) * | 1997-10-20 | 2000-09-26 | Latents Image Technology Ltd. | Polymer materials with latent images visible in polarized light and methods for their production |
GB9817272D0 (en) * | 1998-08-07 | 1998-10-07 | Rolic Ag | Liquid crystalline compounds |
GB9903670D0 (en) * | 1999-02-17 | 1999-04-14 | Rolic Ag | Liquid crystal compounds |
GB9930557D0 (en) * | 1999-12-23 | 2000-02-16 | Rolic Ag | Optically active materials |
DE10016524A1 (de) * | 2000-04-03 | 2001-10-04 | Basf Ag | Polymerisierbare Flüssigkristalle |
JP3619174B2 (ja) * | 2000-07-24 | 2005-02-09 | キヤノン株式会社 | 高分子液晶性化合物、それらを含む電解質および二次電池 |
JP5295471B2 (ja) | 2000-11-13 | 2013-09-18 | Dic株式会社 | 重合性液晶化合物、該化合物を含有する重合性液晶組成物及びその重合体 |
JP4810750B2 (ja) * | 2001-04-11 | 2011-11-09 | Dic株式会社 | 重合性液晶化合物、該化合物を含有する重合性液晶組成物及びその重合体 |
GB0127252D0 (en) * | 2001-11-13 | 2002-01-02 | Vantico Ag | Production of composite articles composed of thin layers |
US6919946B2 (en) * | 2002-04-16 | 2005-07-19 | 3M Innovative Properties Company | Compensators for liquid crystal displays and the use and manufacture of the compensators |
US8574454B2 (en) * | 2006-12-22 | 2013-11-05 | Rolic Ag | Patternable liquid crystal polymer comprising thio-ether units |
JP5345293B2 (ja) * | 2007-03-29 | 2013-11-20 | 株式会社Adeka | 重合性化合物及び重合性組成物 |
DE602008003417D1 (de) * | 2007-03-30 | 2010-12-23 | Merck Patent Gmbh | Doppelbrechungs-polymerfolie mit negativer optischer dispersion |
US8323527B2 (en) * | 2007-09-03 | 2012-12-04 | Merck Patent Gmbh | Fluorene derivatives |
US8697199B2 (en) | 2007-09-03 | 2014-04-15 | Merck Patent Gmbh | Calamitic mesogenic compounds |
WO2009039937A1 (en) | 2007-09-25 | 2009-04-02 | Merck Patent Gmbh | Mesogenic dimers |
CN105733606B (zh) * | 2007-12-21 | 2018-04-03 | 罗利克有限公司 | 光校准组合物 |
EP2222740B1 (en) * | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
US8257639B2 (en) * | 2009-09-22 | 2012-09-04 | Kent State University | Method of making stimuli responsive liquid crystal-polymer composite fibers |
WO2012141245A1 (ja) | 2011-04-15 | 2012-10-18 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
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WO2012176679A1 (ja) | 2011-06-24 | 2012-12-27 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
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WO2013180217A1 (ja) | 2012-05-30 | 2013-12-05 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
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WO2014065176A1 (ja) | 2012-10-23 | 2014-05-01 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
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JP6575360B2 (ja) | 2014-02-12 | 2019-09-18 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
JP6672796B2 (ja) | 2014-02-14 | 2020-03-25 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
CN106068257B (zh) | 2014-03-19 | 2018-09-14 | 日本瑞翁株式会社 | 聚合性化合物的制造方法 |
CN106414617A (zh) | 2014-05-21 | 2017-02-15 | 罗利克有限公司 | 可聚合的二色性染料 |
US10538477B2 (en) * | 2014-06-30 | 2020-01-21 | Zeon Corporation | Production intermediate of polymerizable compound, production method for same, composition, and stabilization method |
JP2016110152A (ja) | 2014-12-08 | 2016-06-20 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 反射防止フィルムおよびこれを備えた有機発光装置 |
KR101623086B1 (ko) | 2014-12-08 | 2016-05-20 | 삼성전자 주식회사 | 반사방지필름 및 이를 구비한 유기발광장치 |
KR20170133350A (ko) | 2015-03-31 | 2017-12-05 | 니폰 제온 가부시키가이샤 | 중합성 화합물의 혼합물 및 그 제조 방법 |
JP6751321B2 (ja) * | 2016-09-06 | 2020-09-02 | 富士フイルム株式会社 | 光学異方性膜、光学フィルム、偏光板および画像表示装置 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0501563A1 (en) * | 1991-02-26 | 1992-09-02 | Koninklijke Philips Electronics N.V. | Device for doubling the frequency of a light wave |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3635584A1 (de) * | 1985-11-11 | 1987-05-14 | Werk Fernsehelektronik Veb | Glasartige nematische fluessigkristalle |
DE3622086A1 (de) * | 1986-07-02 | 1988-01-07 | Basf Ag | Nichtionische, in waessriger loesung scheibchenfoermige mizellen ausbildende tenside |
US5043192A (en) * | 1988-03-15 | 1991-08-27 | North Dakota State University | Polymeric vehicle for coating |
US5093471A (en) * | 1988-04-11 | 1992-03-03 | Kent State University | Novel mesogenic amines and liquid-crystalline-side-group polymers incorporating same |
DE3924554A1 (de) * | 1989-07-25 | 1991-01-31 | Roehm Gmbh | Anisotrope fluessigkristalline polymer-filme |
US5210630A (en) * | 1989-10-18 | 1993-05-11 | U.S. Philips Corporation | Liquid-crystal display device |
DE4124859A1 (de) * | 1991-07-26 | 1993-01-28 | Merck Patent Gmbh | Fluessigkristalline elastomere oder duomere mit fixierter anisotroper netzwerkstruktur |
-
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0501563A1 (en) * | 1991-02-26 | 1992-09-02 | Koninklijke Philips Electronics N.V. | Device for doubling the frequency of a light wave |
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EP0675186B1 (de) | 1999-01-20 |
CN1110984A (zh) | 1995-11-01 |
DE59504854D1 (de) | 1999-03-04 |
JPH07278060A (ja) | 1995-10-24 |
KR950032067A (ko) | 1995-12-20 |
EP0675186A1 (de) | 1995-10-04 |
HK1011042A1 (en) | 1999-07-02 |
JP3866307B2 (ja) | 2007-01-10 |
KR100388405B1 (ko) | 2003-11-01 |
US5567349A (en) | 1996-10-22 |
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