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 |
|---|---|---|---|
| JP50269285 | 1985-06-12 | ||
| WO85/00328 | 1985-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62275163A JPS62275163A (ja) | 1987-11-30 |
| JPH0430987B2 true JPH0430987B2 (ko) | 1992-05-25 |
Family
ID=18527196
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
|---|---|---|---|
| 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 |
| 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 |
Country Status (1)
| Country | Link |
|---|---|
| JP (3) | JPH07104448B2 (ko) |
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 |
| BRPI0715806B1 (pt) | 2006-08-10 | 2018-09-18 | Hopnic Laboratory Co Ltd | lente polarizada plástica e método de produção da mesma |
| US8187712B2 (en) | 2008-02-07 | 2012-05-29 | Mitsui Chemicals, Inc. | Plastic polarized lens and method of producing the same |
| KR101729368B1 (ko) | 2010-08-12 | 2017-04-21 | 미쓰이 가가쿠 가부시키가이샤 | 플라스틱 편광렌즈, 그 제조 방법 및 편광필름 |
| IN2014DN07932A (ko) | 2012-03-06 | 2015-05-01 | Mitsui Chemicals Inc | |
| JP2018514817A (ja) | 2015-04-29 | 2018-06-07 | トライアペックス カンパニー リミテッド | 偏光フィルム、その製造方法、およびこれを含む偏光レンズ |
| US20220112406A1 (en) | 2018-09-26 | 2022-04-14 | Mitsui Chemicals, Inc. | Functional layer with adhesive layer, laminate, and use thereof |
| US20220219361A1 (en) | 2019-05-16 | 2022-07-14 | Mitsui Chemicals, Inc. | Injection molding apparatus, injection molding method and production method of molded product using injection molding apparatus, and laminated lens |
| JPWO2022202182A1 (ko) | 2021-03-22 | 2022-09-29 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50105721A (ko) * | 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 |
| JPS59182878A (ja) * | 1983-04-01 | 1984-10-17 | Hitachi Ltd | ゲスト― ホスト型液晶組成物 |
| JPS59182877A (ja) * | 1983-04-01 | 1984-10-17 | Hitachi Ltd | ゲスト−ホスト型液晶組成物 |
| 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 JP61078452A patent/JPH07104448B2/ja not_active Expired - Lifetime
- 1986-04-04 JP JP7845186A patent/JPS62270664A/ja active Granted
- 1986-04-04 JP JP7845086A patent/JPS62275163A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07104448B2 (ja) | 1995-11-13 |
| JPH0436189B2 (ko) | 1992-06-15 |
| JPS62275163A (ja) | 1987-11-30 |
| JPS62269901A (ja) | 1987-11-24 |
| JPS62270664A (ja) | 1987-11-25 |
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