JPH0430987B2 - - Google Patents
Info
- Publication number
- JPH0430987B2 JPH0430987B2 JP7845086A JP7845086A JPH0430987B2 JP H0430987 B2 JPH0430987 B2 JP H0430987B2 JP 7845086 A JP7845086 A JP 7845086A JP 7845086 A JP7845086 A JP 7845086A JP H0430987 B2 JPH0430987 B2 JP H0430987B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- dye
- atom
- hydrogen atom
- 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
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000001000 anthraquinone dye Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 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 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 66
- 239000004973 liquid crystal related substance Substances 0.000 description 22
- -1 polyethylene terephthalate Polymers 0.000 description 19
- 230000010287 polarization Effects 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 229920000139 polyethylene terephthalate Polymers 0.000 description 13
- 239000005020 polyethylene terephthalate Substances 0.000 description 13
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004040 coloring Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 241000974482 Aricia saepiolus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GCPNYYXFDSGAPA-UHFFFAOYSA-N 4-amino-n-(4-butylphenyl)benzamide Chemical compound C1=CC(CCCC)=CC=C1NC(=O)C1=CC=C(N)C=C1 GCPNYYXFDSGAPA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Optical Filters (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| WO85/00328 | 1985-06-12 | ||
| JP50269285 | 1985-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62275163A JPS62275163A (ja) | 1987-11-30 |
| JPH0430987B2 true JPH0430987B2 (enrdf_load_stackoverflow) | 1992-05-25 |
Family
ID=18527196
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7845186A Granted JPS62270664A (ja) | 1985-06-12 | 1986-04-04 | キノフタロン系色素およびこれを用いた偏光フイルム |
| JP61078452A Expired - Lifetime JPH07104448B2 (ja) | 1985-06-12 | 1986-04-04 | ペリレン系色素を用いた偏光フイルム |
| JP7845086A Granted JPS62275163A (ja) | 1985-06-12 | 1986-04-04 | アントラキノン系色素およびこれを用いた偏光フイルム |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7845186A Granted JPS62270664A (ja) | 1985-06-12 | 1986-04-04 | キノフタロン系色素およびこれを用いた偏光フイルム |
| JP61078452A Expired - Lifetime JPH07104448B2 (ja) | 1985-06-12 | 1986-04-04 | ペリレン系色素を用いた偏光フイルム |
Country Status (1)
| Country | Link |
|---|---|
| JP (3) | JPS62270664A (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02167723A (ja) * | 1988-12-22 | 1990-06-28 | Chisso Corp | 平面集光着色圧延シート又はフィルム及びその製造方法 |
| US5659039A (en) * | 1994-02-25 | 1997-08-19 | Mitsui Toatsu Chemicals, Inc. | Quinophthalone compounds |
| AU6320998A (en) * | 1997-02-21 | 1998-09-09 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| US6432327B2 (en) * | 1999-12-29 | 2002-08-13 | Younger Mfg. Co. | Formed polyethylene terephthalate polarizing film for incorporation in optical-grade plastic parts |
| JP4525280B2 (ja) * | 2004-09-30 | 2010-08-18 | 三菱化学株式会社 | 異方性色素膜用色素、異方性色素膜形成用組成物、異方性色素膜及び偏光素子 |
| WO2008018168A1 (fr) | 2006-08-10 | 2008-02-14 | Mitsui Chemicals, Inc. | Lentille polarisante en plastique et procédé servant à produire celle-ci |
| US8187712B2 (en) | 2008-02-07 | 2012-05-29 | Mitsui Chemicals, Inc. | Plastic polarized lens and method of producing the same |
| BR112013003397B8 (pt) * | 2010-08-12 | 2023-05-09 | Mitsui Chemicals Inc | Lente e película polarizadas de plástico, e métodos para a produção das mesmas |
| AU2013228905B2 (en) | 2012-03-06 | 2015-09-03 | Mitsui Chemicals, Inc. | Plastic polarized lens and method of producing same |
| US10408982B2 (en) | 2015-04-29 | 2019-09-10 | Triaplex Co., Ltd. | Polarizing film, preparation method thereof, polarizing lens comprising the same |
| EP3858931A4 (en) | 2018-09-26 | 2022-06-15 | Mitsui Chemicals, Inc. | FUNCTIONAL LAYER WITH ADHESIVE LAYER, LAMINATE AND THEIR USE |
| WO2020230889A1 (ja) | 2019-05-16 | 2020-11-19 | 三井化学株式会社 | 注入成形装置、当該装置を用いた注入成形方法および成形体の製造方法、積層レンズ |
| EP4318103A4 (en) | 2021-03-22 | 2025-03-26 | Mitsui Chemicals, Inc. | Production method for photochromic lens and photochromic lens |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50105721A (enrdf_load_stackoverflow) * | 1974-01-29 | 1975-08-20 | ||
| JPS51102036A (ja) * | 1975-03-07 | 1976-09-09 | Teijin Ltd | Kobunshizairyonochakushokuhoho |
| JPS58124621A (ja) * | 1982-01-22 | 1983-07-25 | Mitsui Toatsu Chem Inc | 偏光フイルムの製造方法 |
| JPS5936181A (ja) * | 1982-08-25 | 1984-02-28 | Mitsui Toatsu Chem Inc | カラ−液晶組成物 |
| JPS59182877A (ja) * | 1983-04-01 | 1984-10-17 | Hitachi Ltd | ゲスト−ホスト型液晶組成物 |
| JPS59182878A (ja) * | 1983-04-01 | 1984-10-17 | Hitachi Ltd | ゲスト― ホスト型液晶組成物 |
| JPS59223786A (ja) * | 1983-06-03 | 1984-12-15 | Alps Electric Co Ltd | カラ−液晶表示素子用二色性色素 |
-
1986
- 1986-04-04 JP JP7845186A patent/JPS62270664A/ja active Granted
- 1986-04-04 JP JP61078452A patent/JPH07104448B2/ja not_active Expired - Lifetime
- 1986-04-04 JP JP7845086A patent/JPS62275163A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62275163A (ja) | 1987-11-30 |
| JPS62270664A (ja) | 1987-11-25 |
| JPH07104448B2 (ja) | 1995-11-13 |
| JPS62269901A (ja) | 1987-11-24 |
| JPH0436189B2 (enrdf_load_stackoverflow) | 1992-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0198082B1 (en) | Polarizing film | |
| JPH0430987B2 (enrdf_load_stackoverflow) | ||
| EP0348964B1 (en) | Polarizing film | |
| US4128496A (en) | Dichroic liquid crystal compositions | |
| JPS63301850A (ja) | アゾ化合物からなる液晶用二色性色素 | |
| EP0275077B1 (en) | Anthraquinone compounds and polarizing film containing the same | |
| JPH07207169A (ja) | 偏光フィルム用アゾ系色素及びこれを用いた偏光フィルム | |
| JPS61285259A (ja) | 二色性色素およびこれを用いた偏光フイルム | |
| JPS5884858A (ja) | 液晶組成物及び表示体 | |
| JPH01103667A (ja) | アントラキノン系色素および該色素を用いた偏光フィルム | |
| JP2954306B2 (ja) | アントラキノン系偏光フィルム用色素及び該色素を用いた偏光フィルム | |
| US5382465A (en) | Anthraquinonic colorant and polarizing film containing the colorant | |
| US4607097A (en) | Dichromatic coloring matter for a colored liquid crystal display element | |
| JPS62277471A (ja) | アントラキノン化合物及びそれを含有する液晶組成物 | |
| JP2966973B2 (ja) | アントラキノン系色素及び該色素を用いた偏光フィルム | |
| US5750599A (en) | Quinophthalone compounds and polarizing films using same | |
| JP2955329B2 (ja) | アントラキノン系黄色色素及び該色素を用いた偏光フィルム | |
| JP3100461B2 (ja) | 二色性アゾ色素及びこれを用いた偏光フィルム | |
| EP0300770A2 (en) | Polarizing film containing an anthraquinonic colorant | |
| GB2041962A (en) | Guest-host liquid crystal composition | |
| JPS62265356A (ja) | 二色性アゾ色素およびこれを用いた偏光フイルム | |
| JPH042626B2 (enrdf_load_stackoverflow) | ||
| JPS58157883A (ja) | 液晶用二色性色素 | |
| JP2002294092A (ja) | トリフェノジオキサジン化合物、その中間体、それら製造方法並びに二色性色素及び液晶組成物。 | |
| JPS636056A (ja) | アントラキノン染料およびこれを含む液晶組成物 |