JPH026798B2 - - Google Patents
Info
- Publication number
- JPH026798B2 JPH026798B2 JP57069582A JP6958282A JPH026798B2 JP H026798 B2 JPH026798 B2 JP H026798B2 JP 57069582 A JP57069582 A JP 57069582A JP 6958282 A JP6958282 A JP 6958282A JP H026798 B2 JPH026798 B2 JP H026798B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dye
- parts
- water
- 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 - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- -1 boric acid ester Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CUIHODIOWPLCMG-UHFFFAOYSA-N 1,5-dihydroxy-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O CUIHODIOWPLCMG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- GJCHQJDEYFYWER-UHFFFAOYSA-N 1,8-dihydroxy-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O GJCHQJDEYFYWER-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
Description
本発明は式(1)
（式(1)中R1は炭素数１〜15の直鎖又は枝分れし
たアルキルを、又R2は水素又はメチルを表す。）
及び式(2)
（式(2)中、R1，R2は式(1)におけるのと同じ意味
を表す。）
で表される化合物からなるカラー液晶用色素に関
する。
本発明の式(1)及び(2)で表される化合物からなる
アントラキノン系カラー液晶用色素は硫酸中、
１，５―ジヒドロキシ４，８―ジニトロアントラ
キノンの硼酸エステルを式
（式(2)中R1及びR2は式(1)におけるのと同じ意味
を表す）
で表される化合物と反応させた後、縮合反応生成
物中の硼酸エステルをケン化し次いで常法により
ニトロ基を還元してアミノ基とすることによつて
得られる。
又１，５―ジヒドロキシ４，８―ジニトロアン
トラキノンの硼酸エステルを硫酸中式
（式(3)中、R2は式(1)におけるのと同じ意味を表
す）
で表されるフエノール化合物と反応させ得られる
縮合反応生成物中の硼酸エステルをケン化し、次
いで常法によりニトロ基を還元して得られる式
（式(4)中、R2は式(1)におけるのと同じ意味を、
Ｙは水素原子又は
The present invention uses formula (1) (In formula (1), R 1 represents a straight chain or branched alkyl having 1 to 15 carbon atoms, and R 2 represents hydrogen or methyl.) and formula (2) (In formula (2), R 1 and R 2 have the same meanings as in formula (1).) This invention relates to a color liquid crystal dye comprising a compound represented by the following formula. The anthraquinone color liquid crystal dye comprising the compounds represented by formulas (1) and (2) of the present invention is prepared in sulfuric acid,
The boric acid ester of 1,5-dihydroxy 4,8-dinitroanthraquinone is expressed by the formula (In formula (2), R 1 and R 2 represent the same meanings as in formula (1).) After reacting with the compound represented by formula (2), the boric acid ester in the condensation reaction product is saponified, and then by a conventional method. It is obtained by reducing a nitro group to an amino group. In addition, boric acid ester of 1,5-dihydroxy 4,8-dinitroanthraquinone was dissolved in sulfuric acid. (In formula (3), R 2 represents the same meaning as in formula (1)) The boric acid ester in the condensation reaction product obtained by reacting with the phenol compound represented by Formula obtained by reducing the group (In formula (4), R 2 has the same meaning as in formula (1),
Y is a hydrogen atom or
【式】をそれぞれ表
す）
で表される化合物を式
Ｚ―C2H4OR1 (6)
（式(6)中、R1は式(1)におけると同じ意味をＺは
ハロゲンをそれぞれ表す）
で表されるハロゲン化合物、或いは式
（式(7)中、R1は式(1)におけるのと同じ意味を、
Ａは水素原子又はメチルをそれぞれ表す）
で表されるスルホン酸エステルで代表されるアル
キル化剤と脱酸剤の存在下に反応させても式(1)及
び(2)で表される化合物からなる本発明のカラー液
晶用色素が得られる。
本発明のカラー液晶用アントラキノン系化合物
は、ビフエニル系、フエニルシクロヘキサン系、
エステル系、ピリジン系、シツフ系、アゾ系、ア
ゾキシ系などいずれの液晶に対しても優れた溶解
性を有しており、又カラー液晶用色素として要求
される二色性、耐久性もすぐれている。
次に実施例を挙げて説明する。
実施例 １
濃硫酸140部中に、水4.1部、硼酸5.3部、１，
５―ジヒドロキシ４，８―ジニトロアントラキノ
ン3.4部を溶解し、−５℃に冷却する。
次いで、２―ヘキシルオキシエトキシトルエン
5.3部を同温度で滴下し、更に２時間同温度で撹
拌する。次に反応混合物を氷水140部にあけ、95
℃にて２時間撹拌して硼酸エステルを加水分解す
る。冷却後ろ過し、十分水洗する。
得られた結晶をエタノール100部中に懸濁させ
水28部中に硫化ソーダ（純度46.7％）9.7部、苛
性ソーダ0.6部を溶解した液を加えて還流下に２
時間反応する。冷却後水30部を加えろ過し水洗す
る。得られた暗青色の結晶を水64部、濃塩酸15.5
部の溶液に懸濁させ、70℃にて1.5時間撹拌する。
結晶をろ取し、十分水洗後乾燥して粗製色素6.5
部を得た。粗製色素をキシレンに溶解し、不溶解
物をろ別した後、シリカゲルカラムクロマトグラ
フイーにかけ、キシレン―酢酸エチル混合溶媒で
展開して精製し、溶媒を濃縮後析出した結晶をろ
過乾燥して青色の色素を得た。このものは色素１
と色素２の混合物であり、その比率は約４：１で
あつた。
融 点 153〜160℃
この色素のアセトン溶解色は青色である。
λmax 629nm
この色素を次の４種類の液晶化合物
の混合物であるBDH Chemicals Ltd社の液晶Ｅ
―７に２％添加し、ホモジニアス配向処理を、施
した２枚の透明ガラス電極基板を約10μmの間隔
で対向せしめたセル中に封入し、電圧をオン、オ
フす、ると、青色の良好な表示が得られた。
この二色性化は9.5であつた。
実施例 ２
実施例１において、２―ヘキシルオキシエトキ
シトルエンの代りに２―ブトキシエトキシ―ｍ―
キシレン5.1部を用いて同様に反応させて粗製色
素6.4部を得た。カラムクロマトグラフイーで同
様に精製し、青色の色素を得た。このものは色素
３と色素４の混合物であり、その比率は約６：１
であつた。
融 点 157〜163℃
この色素（混合物）のアセトン溶解色は青色で
ある。
λmax 629nm
この色素（混合物）を液晶Ｅ―７に２％添加し
実施例１と同様なセル中に封入し、電圧をオン、
オフすると青色の良好な表示が得られた。その二
色性比は9.2であつた。[Formula] respectively) is a compound represented by the formula Z-C 2 H 4 OR 1 (6) (In formula (6), R 1 has the same meaning as in formula (1), and Z represents a halogen, respectively. ) or a halogen compound represented by the formula (In formula (7), R 1 has the same meaning as in formula (1),
(A represents a hydrogen atom or methyl, respectively) from the compounds represented by formulas (1) and (2) even when reacted in the presence of an alkylating agent represented by a sulfonic acid ester and a deoxidizing agent. The color liquid crystal dye of the present invention is obtained. The anthraquinone compounds for color liquid crystals of the present invention include biphenyl-based, phenylcyclohexane-based,
It has excellent solubility in all types of liquid crystals, including ester, pyridine, Schiff, azo, and azoxy, and also has excellent dichroism and durability, which are required as color liquid crystal pigments. There is. Next, an example will be given and explained. Example 1 In 140 parts of concentrated sulfuric acid, 4.1 parts of water, 5.3 parts of boric acid, 1,
3.4 parts of 5-dihydroxy 4,8-dinitroanthraquinone is dissolved and cooled to -5°C. Then, 2-hexyloxyethoxytoluene
5.3 parts were added dropwise at the same temperature, and the mixture was further stirred at the same temperature for 2 hours. Next, pour the reaction mixture into 140 parts of ice water and
The boric acid ester is hydrolyzed by stirring at ℃ for 2 hours. After cooling, strain and wash thoroughly with water. The obtained crystals were suspended in 100 parts of ethanol, and a solution of 9.7 parts of sodium sulfide (purity 46.7%) and 0.6 parts of caustic soda dissolved in 28 parts of water was added and the mixture was refluxed for 2 hours.
Time reacts. After cooling, add 30 parts of water, filter and wash with water. The obtained dark blue crystals were mixed with 64 parts of water and 15.5 parts of concentrated hydrochloric acid.
of the solution and stirred at 70°C for 1.5 hours.
Filter the crystals, wash thoroughly with water and dry to obtain crude pigment 6.5
I got the department. After dissolving the crude dye in xylene and filtering off insoluble matter, it was subjected to silica gel column chromatography and purified by developing with a mixed solvent of xylene and ethyl acetate. After concentrating the solvent, the precipitated crystals were filtered and dried to give a blue color. The dye was obtained. This one is dye 1
and Dye 2 in a ratio of approximately 4:1. Melting point: 153-160°C The color of this dye dissolved in acetone is blue. λmax 629nm This dye is combined with the following four types of liquid crystal compounds. BDH Chemicals Ltd.'s Liquid Crystal E, which is a mixture of
- When two transparent glass electrode substrates containing 2% of 7 and subjected to homogeneous alignment treatment are placed in a cell facing each other with a spacing of about 10 μm, and the voltage is turned on and off, a good blue color appears. A display was obtained. This dichroism was 9.5. Example 2 In Example 1, 2-butoxyethoxy-m- was used instead of 2-hexyloxyethoxytoluene.
A similar reaction was carried out using 5.1 parts of xylene to obtain 6.4 parts of a crude dye. The product was similarly purified by column chromatography to obtain a blue pigment. This is a mixture of dye 3 and dye 4, with a ratio of about 6:1.
It was hot. Melting point: 157-163°C The color of this dye (mixture) dissolved in acetone is blue. λmax 629nm 2% of this dye (mixture) was added to liquid crystal E-7, sealed in the same cell as in Example 1, and the voltage was turned on.
When turned off, a good blue display was obtained. Its dichroic ratio was 9.2.
Claims (1)
アルキルを、又R2は水素又はメチルを表す。） 及び式(2) （式中R1，R2は式(1)におけるのと同じ意味を表
す。） で表される化合物からなるカラー液晶用色素。[Claims] 1 Formula (1) (In the formula, R 1 represents a straight chain or branched alkyl having 1 to 15 carbon atoms, and R 2 represents hydrogen or methyl.) and Formula (2) (In the formula, R 1 and R 2 have the same meanings as in formula (1).) A dye for color liquid crystals consisting of a compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6958282A JPS58187454A (en) | 1982-04-27 | 1982-04-27 | Anthraquinone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6958282A JPS58187454A (en) | 1982-04-27 | 1982-04-27 | Anthraquinone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58187454A JPS58187454A (en) | 1983-11-01 |
| JPH026798B2 true JPH026798B2 (en) | 1990-02-13 |
Family
ID=13406948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6958282A Granted JPS58187454A (en) | 1982-04-27 | 1982-04-27 | Anthraquinone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58187454A (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3216455A1 (en) * | 1982-05-03 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | ANTHRACHINONE DYES, THEIR PRODUCTION AND USE, AND SEALANT MATERIAL CONTAINING THESE ANTHRACHINONE DYES |
| US5910393A (en) * | 1987-06-10 | 1999-06-08 | Mitsubishi Denki Kabushiki Kaisha | Optical recording material |
| US8192474B2 (en) | 2006-09-26 | 2012-06-05 | Zeltiq Aesthetics, Inc. | Tissue treatment methods |
| US9132031B2 (en) | 2006-09-26 | 2015-09-15 | Zeltiq Aesthetics, Inc. | Cooling device having a plurality of controllable cooling elements to provide a predetermined cooling profile |
| US20080077201A1 (en) | 2006-09-26 | 2008-03-27 | Juniper Medical, Inc. | Cooling devices with flexible sensors |
| US20080287839A1 (en) | 2007-05-18 | 2008-11-20 | Juniper Medical, Inc. | Method of enhanced removal of heat from subcutaneous lipid-rich cells and treatment apparatus having an actuator |
| US8523927B2 (en) | 2007-07-13 | 2013-09-03 | Zeltiq Aesthetics, Inc. | System for treating lipid-rich regions |
| EP3488833A1 (en) | 2007-08-21 | 2019-05-29 | Zeltiq Aesthetics, Inc. | Monitoring the cooling of subcutaneous lipid-rich cells, such as the cooling of adipose tissue |
| US8603073B2 (en) | 2008-12-17 | 2013-12-10 | Zeltiq Aesthetics, Inc. | Systems and methods with interrupt/resume capabilities for treating subcutaneous lipid-rich cells |
| BRPI1014623B1 (en) | 2009-04-30 | 2020-01-07 | Zeltiq Aesthetics, Inc. | SYSTEM FOR TREATING SUBCUTANEOUS CELLS RICH IN LIPIDS IN A TARGET AREA |
| US9314368B2 (en) | 2010-01-25 | 2016-04-19 | Zeltiq Aesthetics, Inc. | Home-use applicators for non-invasively removing heat from subcutaneous lipid-rich cells via phase change coolants, and associates devices, systems and methods |
| US8676338B2 (en) | 2010-07-20 | 2014-03-18 | Zeltiq Aesthetics, Inc. | Combined modality treatment systems, methods and apparatus for body contouring applications |
| US9545523B2 (en) | 2013-03-14 | 2017-01-17 | Zeltiq Aesthetics, Inc. | Multi-modality treatment systems, methods and apparatus for altering subcutaneous lipid-rich tissue |
| US9844460B2 (en) | 2013-03-14 | 2017-12-19 | Zeltiq Aesthetics, Inc. | Treatment systems with fluid mixing systems and fluid-cooled applicators and methods of using the same |
| EP3099258B1 (en) | 2014-01-31 | 2024-02-21 | Zeltiq Aesthetics, Inc. | Compositions and treatment systems for improved cooling of lipid-rich tissue |
| US10675176B1 (en) | 2014-03-19 | 2020-06-09 | Zeltiq Aesthetics, Inc. | Treatment systems, devices, and methods for cooling targeted tissue |
| USD777338S1 (en) | 2014-03-20 | 2017-01-24 | Zeltiq Aesthetics, Inc. | Cryotherapy applicator for cooling tissue |
| US10952891B1 (en) | 2014-05-13 | 2021-03-23 | Zeltiq Aesthetics, Inc. | Treatment systems with adjustable gap applicators and methods for cooling tissue |
| US10568759B2 (en) | 2014-08-19 | 2020-02-25 | Zeltiq Aesthetics, Inc. | Treatment systems, small volume applicators, and methods for treating submental tissue |
| US10935174B2 (en) | 2014-08-19 | 2021-03-02 | Zeltiq Aesthetics, Inc. | Stress relief couplings for cryotherapy apparatuses |
| WO2017070112A1 (en) | 2015-10-19 | 2017-04-27 | Zeltiq Aesthetics, Inc. | Vascular treatment systems, cooling devices, and methods for cooling vascular structures |
| EP3399950A1 (en) | 2016-01-07 | 2018-11-14 | Zeltiq Aesthetics, Inc. | Temperature-dependent adhesion between applicator and skin during cooling of tissue |
| US10765552B2 (en) | 2016-02-18 | 2020-09-08 | Zeltiq Aesthetics, Inc. | Cooling cup applicators with contoured heads and liner assemblies |
| US10555831B2 (en) | 2016-05-10 | 2020-02-11 | Zeltiq Aesthetics, Inc. | Hydrogel substances and methods of cryotherapy |
| US11382790B2 (en) | 2016-05-10 | 2022-07-12 | Zeltiq Aesthetics, Inc. | Skin freezing systems for treating acne and skin conditions |
| US10682297B2 (en) | 2016-05-10 | 2020-06-16 | Zeltiq Aesthetics, Inc. | Liposomes, emulsions, and methods for cryotherapy |
| US11076879B2 (en) | 2017-04-26 | 2021-08-03 | Zeltiq Aesthetics, Inc. | Shallow surface cryotherapy applicators and related technology |
| AU2019315940A1 (en) | 2018-07-31 | 2021-03-04 | Zeltiq Aesthetics, Inc. | Methods, devices, and systems for improving skin characteristics |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5411430A (en) * | 1977-06-27 | 1979-01-27 | Western Electric Co | Nonaqueous secondary battery |
| JPS54120637A (en) * | 1978-02-17 | 1979-09-19 | Bayer Ag | Anthraquinone dye |
| JPS55155082A (en) * | 1979-05-22 | 1980-12-03 | Mitsui Toatsu Chem Inc | Liquid crystal color display composition |
| JPS5712064A (en) * | 1980-06-27 | 1982-01-21 | Mitsui Toatsu Chem Inc | Preparation of anthraquinone-base dispersion dye |
-
1982
- 1982-04-27 JP JP6958282A patent/JPS58187454A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5411430A (en) * | 1977-06-27 | 1979-01-27 | Western Electric Co | Nonaqueous secondary battery |
| JPS54120637A (en) * | 1978-02-17 | 1979-09-19 | Bayer Ag | Anthraquinone dye |
| JPS55155082A (en) * | 1979-05-22 | 1980-12-03 | Mitsui Toatsu Chem Inc | Liquid crystal color display composition |
| JPS5712064A (en) * | 1980-06-27 | 1982-01-21 | Mitsui Toatsu Chem Inc | Preparation of anthraquinone-base dispersion dye |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58187454A (en) | 1983-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH026798B2 (en) | ||
| JPS6119672B2 (en) | ||
| JPH0442438B2 (en) | ||
| US4126610A (en) | Process for the preparation of cyano azo dyestuffs | |
| US4289694A (en) | Process for the industrial preparation of water insoluble azo dyestuffs containing cyano groups from the corresponding halogen compounds | |
| JPS6362553B2 (en) | ||
| JPH0375580B2 (en) | ||
| JPH044344B2 (en) | ||
| JPH01146960A (en) | Dichroic disazo coloring matter | |
| US4165297A (en) | Catalyst complex for the preparation of cyano-azo dyestuffs | |
| EP0306526A1 (en) | Phase change dyestuffs | |
| JPH0316389B2 (en) | ||
| EP0307866B1 (en) | Dichroic coloring agents for liquid crystal displays | |
| US4597891A (en) | Liquid crystal compositions and devices and novel compounds | |
| JPS6160828B2 (en) | ||
| JPH0429701B2 (en) | ||
| JPS5929070B2 (en) | 3-Amino-4-carbalkoxybenzoic acid-4'-phenoxyanilide and its production and use method | |
| US2542597A (en) | Urethanes of 2-naphthyl j acid and their brominated derivatives | |
| JP3243837B2 (en) | Pyridone compounds | |
| JPS6372760A (en) | Anthraquinone compound and liquid crystal composition containing the same | |
| JPS6335193B2 (en) | ||
| US2154709A (en) | Polynuclear aryl thioisatins | |
| CA1338740C (en) | N-alkyl-n(aminophenylsulfonyl)-aminoalkylphosphonic acids | |
| JPH05255221A (en) | Production of perfluoroalkyl-substituted azo compound | |
| US1904366A (en) | Organic acid of the diphenyl-methane series and a process of preparing the same |