KR20040035864A - 이소소르바이드 유도체 - Google Patents
이소소르바이드 유도체 Download PDFInfo
- Publication number
- KR20040035864A KR20040035864A KR10-2004-7004171A KR20047004171A KR20040035864A KR 20040035864 A KR20040035864 A KR 20040035864A KR 20047004171 A KR20047004171 A KR 20047004171A KR 20040035864 A KR20040035864 A KR 20040035864A
- Authority
- KR
- South Korea
- Prior art keywords
- isosorbide
- group
- derivative
- hydroxy
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical class O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 title claims abstract description 78
- 229960002479 isosorbide Drugs 0.000 claims abstract description 34
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- -1 and CN Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 238000007699 photoisomerization reaction Methods 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 230000003098 cholesteric effect Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 150000001336 alkenes Chemical group 0.000 claims description 2
- 238000010931 ester hydrolysis Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000012299 nitrogen atmosphere Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- CXTGXXWYCILIBN-UHFFFAOYSA-N 4-[4-(6-prop-2-enoyloxyhexoxy)benzoyl]oxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 CXTGXXWYCILIBN-UHFFFAOYSA-N 0.000 description 13
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000005457 ice water Substances 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- 239000011295 pitch Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- SODCXWMZTUIROQ-VOTSOKGWSA-N 1-(chloromethyl)-4-[(e)-2-(4-hexoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OCCCCCC)=CC=C1\C=C\C1=CC=C(CCl)C=C1 SODCXWMZTUIROQ-VOTSOKGWSA-N 0.000 description 6
- PTUPIHXFSSYBFY-UHFFFAOYSA-N 1-hexoxy-4-(2-phenylethenyl)benzene Chemical compound C1=CC(OCCCCCC)=CC=C1C=CC1=CC=CC=C1 PTUPIHXFSSYBFY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- ROPFOQCOQALTKZ-FMIVXFBMSA-N (e)-3-[4-(6-prop-2-enoyloxyhexoxy)phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 ROPFOQCOQALTKZ-FMIVXFBMSA-N 0.000 description 5
- OOUIOHASXNAAAE-UHFFFAOYSA-N 3-[4-(6-hydroxyhexoxy)phenyl]prop-2-enoic acid Chemical compound OCCCCCCOC1=CC=C(C=CC(O)=O)C=C1 OOUIOHASXNAAAE-UHFFFAOYSA-N 0.000 description 5
- WERYCSOZRQVXCD-UHFFFAOYSA-N [4-(ethoxymethoxycarbonyl)phenyl] 4-(6-prop-2-enoyloxyhexoxy)benzoate Chemical compound C1=CC(C(=O)OCOCC)=CC=C1OC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 WERYCSOZRQVXCD-UHFFFAOYSA-N 0.000 description 5
- 229940114081 cinnamate Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- OSVGDVPVEZILLR-UHFFFAOYSA-N ethoxymethyl 4-hydroxybenzoate Chemical compound CCOCOC(=O)C1=CC=C(O)C=C1 OSVGDVPVEZILLR-UHFFFAOYSA-N 0.000 description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- ROPFOQCOQALTKZ-UHFFFAOYSA-N 3-[4-(6-prop-2-enoyloxyhexoxy)phenyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(OCCCCCCOC(=O)C=C)C=C1 ROPFOQCOQALTKZ-UHFFFAOYSA-N 0.000 description 4
- YCKLLCWNZUJZHZ-UHFFFAOYSA-N 4-(6-hydroxyhexoxy)benzaldehyde Chemical compound OCCCCCCOC1=CC=C(C=O)C=C1 YCKLLCWNZUJZHZ-UHFFFAOYSA-N 0.000 description 4
- BTEKIKIERWOXJT-BQYQJAHWSA-N 4-[(e)-2-[4-(6-prop-2-enoyloxyhexoxy)phenyl]ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 BTEKIKIERWOXJT-BQYQJAHWSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- OQGAFLYIRLUJRB-VOTSOKGWSA-N [4-[(e)-2-(4-hexoxyphenyl)ethenyl]phenyl]methanol Chemical compound C1=CC(OCCCCCC)=CC=C1\C=C\C1=CC=C(CO)C=C1 OQGAFLYIRLUJRB-VOTSOKGWSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 4
- 238000000411 transmission spectrum Methods 0.000 description 4
- FNKRSQLBWMRWJR-UHFFFAOYSA-N (4-carboxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(C(=O)O)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FNKRSQLBWMRWJR-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OJGBZZODVYGQHR-AATRIKPKSA-N 4-[(e)-2-[4-(6-hydroxyhexoxy)phenyl]ethenyl]benzoic acid Chemical compound C1=CC(OCCCCCCO)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 OJGBZZODVYGQHR-AATRIKPKSA-N 0.000 description 3
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- NJJDEEJTWSBBAV-UHFFFAOYSA-N 1-hexoxy-2-(2-phenylethenyl)benzene Chemical compound CCCCCCOC1=CC=CC=C1C=CC1=CC=CC=C1 NJJDEEJTWSBBAV-UHFFFAOYSA-N 0.000 description 2
- NWIYHNKGLAEAQK-UHFFFAOYSA-N 3-[4-(oxan-2-yloxy)phenyl]prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1OC1OCCCC1 NWIYHNKGLAEAQK-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XMFAGJAVLGYUCS-UHFFFAOYSA-M (4-hexoxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(OCCCCCC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XMFAGJAVLGYUCS-UHFFFAOYSA-M 0.000 description 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical group CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CQQSQBRPAJSTFB-UHFFFAOYSA-N 4-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1 CQQSQBRPAJSTFB-UHFFFAOYSA-N 0.000 description 1
- ZFHUHPNDGVGXMS-UHFFFAOYSA-N 4-(hydroxymethyl)benzaldehyde Chemical compound OCC1=CC=C(C=O)C=C1 ZFHUHPNDGVGXMS-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- DLRFDDKZTOPCKE-UHFFFAOYSA-N 6-(4-carbonochloridoylphenoxy)hexyl prop-2-enoate Chemical compound ClC(=O)C1=CC=C(OCCCCCCOC(=O)C=C)C=C1 DLRFDDKZTOPCKE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 150000002729 menthone derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203609.1 | 2001-09-24 | ||
| EP01203609 | 2001-09-24 | ||
| PCT/IB2002/003700 WO2003027119A1 (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040035864A true KR20040035864A (ko) | 2004-04-29 |
Family
ID=8180961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7004171A Withdrawn KR20040035864A (ko) | 2001-09-24 | 2002-09-18 | 이소소르바이드 유도체 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7311948B2 (enExample) |
| EP (1) | EP1432716A1 (enExample) |
| JP (1) | JP2005505577A (enExample) |
| KR (1) | KR20040035864A (enExample) |
| CN (1) | CN1556812A (enExample) |
| WO (1) | WO2003027119A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190011873A (ko) | 2017-07-25 | 2019-02-08 | 순천대학교 산학협력단 | 항균활성을 나타내는 이소소르비드 유도체 및 이를 유효성분으로 포함하는 항균용 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4188058B2 (ja) * | 2002-11-05 | 2008-11-26 | ダイセル化学工業株式会社 | フォトレジスト用高分子化合物及びフォトレジスト用樹脂組成物 |
| CN100497441C (zh) * | 2004-09-29 | 2009-06-10 | 清华大学 | 含有异山梨醇单元的聚酰亚胺及其制备方法 |
| CN1298765C (zh) * | 2005-07-01 | 2007-02-07 | 清华大学 | 含有异山梨醇单元的聚酯酰胺及其制备方法 |
| JP2007176870A (ja) * | 2005-12-28 | 2007-07-12 | Nippon Zeon Co Ltd | キラル剤 |
| US20070189990A1 (en) * | 2006-02-16 | 2007-08-16 | Anthony East | Ultraviolet absorber for cosmetics and polymeric materials |
| TWI429404B (zh) * | 2008-03-03 | 2014-03-11 | Senomyx Inc | 異山梨醇衍生物及彼等作為風味改良劑、促味劑及促味增強劑之用途 |
| JP2010181852A (ja) * | 2008-07-14 | 2010-08-19 | Fujifilm Corp | 光学異方性膜、光学異方性膜の製造方法、液晶セル用基板、及び液晶表示装置 |
| WO2010038591A1 (ja) * | 2008-10-01 | 2010-04-08 | 日本ゼオン株式会社 | 重合性キラル化合物、重合性液晶組成物、液晶性高分子及び光学異方体 |
| EP2301941B1 (en) * | 2009-09-10 | 2013-06-19 | Cognis IP Management GmbH | Isosorbide glyceryl ether derivatives and their use in household applications |
| JP5270510B2 (ja) * | 2009-10-19 | 2013-08-21 | 第一工業製薬株式会社 | 環状（メタ）アクリレート化合物、その製造方法、及び樹脂組成物 |
| TWI410424B (zh) * | 2009-11-12 | 2013-10-01 | Ind Tech Res Inst | 旋光性化合物及含有此化合物之液晶組成物 |
| CN102093377B (zh) * | 2009-12-10 | 2012-11-28 | 财团法人工业技术研究院 | 手性化合物及含有此化合物的液晶组合物 |
| TWI414527B (zh) | 2010-10-06 | 2013-11-11 | Ind Tech Res Inst | 異山梨糖醇衍生物及包含該衍生物之液晶顯示器 |
| US8613507B2 (en) | 2010-10-18 | 2013-12-24 | Xerox Corporation | Curable phase change inks containing functionalized isosorbides |
| JP5594243B2 (ja) | 2011-07-14 | 2014-09-24 | 信越化学工業株式会社 | 重合性エステル化合物、高分子化合物、レジスト材料及びパターン形成方法 |
| US9441164B2 (en) | 2013-07-31 | 2016-09-13 | Semiconductor Energy Laboratory Co., Ltd. | Isosorbide derivative, liquid crystal composition, liquid crystal element, and liquid crystal display device |
| CA2934447A1 (en) * | 2013-12-20 | 2015-06-25 | Archer Daniels Midland Company | Synthesis of isohexide ethers and carbonates |
| CN109535170A (zh) * | 2018-11-30 | 2019-03-29 | 先尼科化工（上海）有限公司 | 一种手性掺杂剂h的合成方法 |
| CN113881417B (zh) * | 2020-07-01 | 2023-04-07 | 中国石油化工股份有限公司 | 含失水山梨醇聚醚羧酸酯的化学剂组合物及其制法和其降低co2驱最小混相压力的方法 |
| US20250361445A1 (en) * | 2022-06-10 | 2025-11-27 | Merck Patent Gmbh | Polymerisable liquid crystal medium and polymerised liquid crystal film |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4342280A1 (de) * | 1993-12-11 | 1995-06-14 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19520704A1 (de) * | 1995-06-09 | 1996-12-12 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE19541820A1 (de) * | 1995-11-09 | 1997-05-15 | Consortium Elektrochem Ind | Chirale Dianhydrohexit-Derivate enthaltende flüssigkristalline Organosiloxane |
| WO1998000428A1 (en) | 1996-07-01 | 1998-01-08 | Merck Patent Gmbh | Chiral dopants |
| JP3996235B2 (ja) * | 1996-10-02 | 2007-10-24 | 日東電工株式会社 | 光学活性モノマー、液晶ポリマー及び光学素子 |
| CN1122034C (zh) | 1997-04-28 | 2003-09-24 | 日东电工株式会社 | 光学活性单体、液晶聚合物和光学元件 |
| DE19726051A1 (de) * | 1997-06-19 | 1998-12-24 | Consortium Elektrochem Ind | Verfahren und Verbreiterung cholesterischer Reflexionsbanden von photopolymerisierbaren cholesterischen Flüssigkristallen und optische Elemente hergestellt nach diesem Verfahren |
| DE19913604A1 (de) * | 1999-03-25 | 2000-09-28 | Basf Ag | Chirale Verbindungen und deren Verwendung als chirale Dotierstoffe zur Herstellung von cholesterisch-flüssigkristallinen Zusammensetzungen |
| GB9930557D0 (en) * | 1999-12-23 | 2000-02-16 | Rolic Ag | Optically active materials |
| JP2001323266A (ja) * | 2000-05-19 | 2001-11-22 | Nitto Denko Corp | コレステリック性液晶組成物、配向フィルムおよび多色反射板 |
| US6589445B2 (en) * | 2000-06-27 | 2003-07-08 | Fuji Photo Film Co., Ltd. | Light-reaction type optically active compound, light-reaction type chiral agent, liquid crystal composition, liquid crystal color filter, optical film, recording medium, and method of changing twist structure of liquid crystal |
| TW555837B (en) * | 2001-07-02 | 2003-10-01 | Merck Patent Gmbh | Chiral compounds |
| US6902687B2 (en) * | 2002-04-18 | 2005-06-07 | Fuji Photo Film Co., Ltd. | Optically active isosorbide derivative and optically active isomannide derivative, production methods thereof, photo-reactive chiral agent, liquid crystal composition, liquid crystal color filter, optical film and recording medium, method for changing helical structure of liquid crystal and method for fixing helical structure of liquid crystal |
-
2002
- 2002-09-18 KR KR10-2004-7004171A patent/KR20040035864A/ko not_active Withdrawn
- 2002-09-18 EP EP02799442A patent/EP1432716A1/en not_active Ceased
- 2002-09-18 CN CNA028186419A patent/CN1556812A/zh active Pending
- 2002-09-18 WO PCT/IB2002/003700 patent/WO2003027119A1/en not_active Ceased
- 2002-09-18 US US10/490,723 patent/US7311948B2/en not_active Expired - Fee Related
- 2002-09-18 JP JP2003530707A patent/JP2005505577A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190011873A (ko) | 2017-07-25 | 2019-02-08 | 순천대학교 산학협력단 | 항균활성을 나타내는 이소소르비드 유도체 및 이를 유효성분으로 포함하는 항균용 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1432716A1 (en) | 2004-06-30 |
| CN1556812A (zh) | 2004-12-22 |
| US20040232383A1 (en) | 2004-11-25 |
| JP2005505577A (ja) | 2005-02-24 |
| WO2003027119A1 (en) | 2003-04-03 |
| US7311948B2 (en) | 2007-12-25 |
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| PA0105 | International application |
Patent event date: 20040322 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |