JPH0314032B2 - - Google Patents
Info
- Publication number
- JPH0314032B2 JPH0314032B2 JP3773582A JP3773582A JPH0314032B2 JP H0314032 B2 JPH0314032 B2 JP H0314032B2 JP 3773582 A JP3773582 A JP 3773582A JP 3773582 A JP3773582 A JP 3773582A JP H0314032 B2 JPH0314032 B2 JP H0314032B2
- Authority
- JP
- Japan
- Prior art keywords
- coumarinyl
- cyano
- formula
- mol
- 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
- 239000000203 mixture Substances 0.000 claims description 23
- 239000004973 liquid crystal related substance Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- -1 coumarinyl ester Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- IJQYTHQDUDCJEQ-UHFFFAOYSA-N 7-hydroxy-2-oxochromene-3-carbonitrile Chemical compound C1=C(C#N)C(=O)OC2=CC(O)=CC=C21 IJQYTHQDUDCJEQ-UHFFFAOYSA-N 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical class C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BVLVGYXYGXOSOG-UHFFFAOYSA-N 2-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=CC=C1C(O)=O BVLVGYXYGXOSOG-UHFFFAOYSA-N 0.000 description 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 2
- AAHNIBROSVVFRO-UHFFFAOYSA-N 3-(4-butoxyphenyl)prop-2-enoic acid Chemical compound CCCCOC1=CC=C(C=CC(O)=O)C=C1 AAHNIBROSVVFRO-UHFFFAOYSA-N 0.000 description 2
- ROJSHRRZPUIDTL-UHFFFAOYSA-N 4-(4-butoxybenzoyl)oxybenzoic acid Chemical compound C1=CC(OCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C=C1 ROJSHRRZPUIDTL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NPKQECBJMVHADY-UHFFFAOYSA-N 1-[4-(4-butoxyphenyl)phenyl]ethanone Chemical group C1=CC(OCCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 NPKQECBJMVHADY-UHFFFAOYSA-N 0.000 description 1
- LMOXYMSDLCVONT-UHFFFAOYSA-N 1-[4-(4-propylphenyl)phenyl]ethanone Chemical group C1=CC(CCC)=CC=C1C1=CC=C(C(C)=O)C=C1 LMOXYMSDLCVONT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- NCJZHZJABHDELF-UHFFFAOYSA-N 1-butoxy-4-phenylbenzene Chemical group C1=CC(OCCCC)=CC=C1C1=CC=CC=C1 NCJZHZJABHDELF-UHFFFAOYSA-N 0.000 description 1
- NAYIXKXYHOLMRC-UHFFFAOYSA-N 1-phenyl-4-propylbenzene Chemical group C1=CC(CCC)=CC=C1C1=CC=CC=C1 NAYIXKXYHOLMRC-UHFFFAOYSA-N 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- JCYPDKSGYHGCCY-UHFFFAOYSA-N 2-pentylbenzoic acid Chemical compound CCCCCC1=CC=CC=C1C(O)=O JCYPDKSGYHGCCY-UHFFFAOYSA-N 0.000 description 1
- VCDLHEZKGKZKIZ-UHFFFAOYSA-N 3-butoxy-4-phenylbenzoic acid Chemical compound CCCCOC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 VCDLHEZKGKZKIZ-UHFFFAOYSA-N 0.000 description 1
- CMNSCPHEWQDYHW-UHFFFAOYSA-N 4-(4-butoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 CMNSCPHEWQDYHW-UHFFFAOYSA-N 0.000 description 1
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001564 phenyl benzoates Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3773582A JPS58154569A (ja) | 1982-03-09 | 1982-03-09 | クマリニル・エステル誘導体およびその製造方法および液晶組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3773582A JPS58154569A (ja) | 1982-03-09 | 1982-03-09 | クマリニル・エステル誘導体およびその製造方法および液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154569A JPS58154569A (ja) | 1983-09-14 |
| JPH0314032B2 true JPH0314032B2 (ru) | 1991-02-25 |
Family
ID=12505737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3773582A Granted JPS58154569A (ja) | 1982-03-09 | 1982-03-09 | クマリニル・エステル誘導体およびその製造方法および液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58154569A (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006232727A (ja) * | 2005-02-24 | 2006-09-07 | Chisso Corp | クマリン誘導体、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 |
-
1982
- 1982-03-09 JP JP3773582A patent/JPS58154569A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58154569A (ja) | 1983-09-14 |
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