JPH0549710B2 - - Google Patents
Info
- Publication number
- JPH0549710B2 JPH0549710B2 JP59085031A JP8503184A JPH0549710B2 JP H0549710 B2 JPH0549710 B2 JP H0549710B2 JP 59085031 A JP59085031 A JP 59085031A JP 8503184 A JP8503184 A JP 8503184A JP H0549710 B2 JPH0549710 B2 JP H0549710B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl group
- lower alkyl
- group
- 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 - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- -1 disazo compound Chemical class 0.000 description 55
- 239000000975 dye Substances 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 238000005859 coupling reaction Methods 0.000 description 27
- 230000008878 coupling Effects 0.000 description 22
- 238000010168 coupling process Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 238000006193 diazotization reaction Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- IXXLKTZOCSRXEM-UHFFFAOYSA-N 3-(n-methylanilino)propanenitrile Chemical compound N#CCCN(C)C1=CC=CC=C1 IXXLKTZOCSRXEM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
- HGBHPZVIOXGKKN-UHFFFAOYSA-N 5-butylthieno[2,3-d][1,3]thiazol-2-amine Chemical compound S1C(N)=NC2=C1C=C(CCCC)S2 HGBHPZVIOXGKKN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical compound C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 description 1
- LTWZRQGFGWBHIQ-UHFFFAOYSA-N 2-aminothieno[2,3-d][1,3]thiazole-5-carbonitrile Chemical compound S1C(C#N)=CC2=C1N=C(N)S2 LTWZRQGFGWBHIQ-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- ATPFNGXOEOASDV-UHFFFAOYSA-N 5-methylthieno[2,3-d][1,3]thiazol-2-amine Chemical compound S1C(N)=NC2=C1C=C(C)S2 ATPFNGXOEOASDV-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RBRCCWBAMGPRSN-UHFFFAOYSA-N thieno[2,3-d][1,3]thiazole Chemical compound S1C=NC2=C1C=CS2 RBRCCWBAMGPRSN-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8503184A JPS60228568A (ja) | 1984-04-26 | 1984-04-26 | 液晶用二色性染料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8503184A JPS60228568A (ja) | 1984-04-26 | 1984-04-26 | 液晶用二色性染料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60228568A JPS60228568A (ja) | 1985-11-13 |
| JPH0549710B2 true JPH0549710B2 (es) | 1993-07-27 |
Family
ID=13847330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8503184A Granted JPS60228568A (ja) | 1984-04-26 | 1984-04-26 | 液晶用二色性染料 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60228568A (es) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020241312A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ用偏光板 |
| WO2020241313A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ |
| US11899167B2 (en) | 2019-05-28 | 2024-02-13 | Toyobo Co., Ltd. | Polyester film, laminated film, and use thereof |
| US11926720B2 (en) | 2019-05-28 | 2024-03-12 | Toyobo Co., Ltd. | Polyester film and application therefor |
| US11934226B2 (en) | 2019-02-08 | 2024-03-19 | Toyobo Co., Ltd. | Foldable display and portable terminal device |
| US11939499B2 (en) | 2019-05-28 | 2024-03-26 | Toyobo Co., Ltd. | Multilayer film and use of same |
| US11997916B2 (en) | 2019-02-08 | 2024-05-28 | Toyobo Co., Ltd. | Polyester film and use thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59204659A (ja) * | 1983-05-04 | 1984-11-20 | Casio Comput Co Ltd | 液晶用二色性染料 |
| DE3622136A1 (de) * | 1986-07-02 | 1988-01-07 | Basf Ag | Thienothiophenfarbstoffe |
| US4959172A (en) * | 1987-06-04 | 1990-09-25 | Mitsubishi Kasei Corporation | Liquid crystal composition containing a pleochroic azo type compound |
| JP5322463B2 (ja) * | 2008-03-11 | 2013-10-23 | 公立大学法人大阪府立大学 | アゾ系二色性色素 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1533260A (en) * | 1976-11-08 | 1978-11-22 | Ici Ltd | Water soluble azo dyestuffs |
| GB1549185A (en) * | 1976-07-21 | 1979-08-01 | Ici Ltd | Monoazo dyestuffs |
-
1984
- 1984-04-26 JP JP8503184A patent/JPS60228568A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1549185A (en) * | 1976-07-21 | 1979-08-01 | Ici Ltd | Monoazo dyestuffs |
| GB1533260A (en) * | 1976-11-08 | 1978-11-22 | Ici Ltd | Water soluble azo dyestuffs |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11934226B2 (en) | 2019-02-08 | 2024-03-19 | Toyobo Co., Ltd. | Foldable display and portable terminal device |
| US11997916B2 (en) | 2019-02-08 | 2024-05-28 | Toyobo Co., Ltd. | Polyester film and use thereof |
| US11899167B2 (en) | 2019-05-28 | 2024-02-13 | Toyobo Co., Ltd. | Polyester film, laminated film, and use thereof |
| US11926720B2 (en) | 2019-05-28 | 2024-03-12 | Toyobo Co., Ltd. | Polyester film and application therefor |
| US11939499B2 (en) | 2019-05-28 | 2024-03-26 | Toyobo Co., Ltd. | Multilayer film and use of same |
| WO2020241312A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ用偏光板 |
| WO2020241313A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60228568A (ja) | 1985-11-13 |
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