JPH0261988B2 - - Google Patents
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- Publication number
- JPH0261988B2 JPH0261988B2 JP1753583A JP1753583A JPH0261988B2 JP H0261988 B2 JPH0261988 B2 JP H0261988B2 JP 1753583 A JP1753583 A JP 1753583A JP 1753583 A JP1753583 A JP 1753583A JP H0261988 B2 JPH0261988 B2 JP H0261988B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- acid
- parts
- compound
- 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
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- -1 disazo compound Chemical class 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QEAYLNJEDDOYNQ-UHFFFAOYSA-N 6-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=C1NC1=CC=CC=C1 QEAYLNJEDDOYNQ-UHFFFAOYSA-N 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZCNCWYFISJTFHB-UHFFFAOYSA-N 4-hydroxy-7-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZCNCWYFISJTFHB-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
本発明は水溶性ジスアゾ化合物に関する。更に
詳しくは遊離酸として一般式
（式（）においてＸは水素原子、メチル基、
メトキシ基又はエトキシ基を、Ｙはメトキシ基又
はエトキシ基を、R1は水素原子又はメチル基を
R2は水素原子、メチル基、−C2H4OH基、
The present invention relates to water-soluble disazo compounds. More specifically, as a free acid, the general formula (In formula (), X is a hydrogen atom, a methyl group,
methoxy group or ethoxy group, Y is methoxy group or ethoxy group, R 1 is hydrogen atom or methyl group.
R 2 is a hydrogen atom, a methyl group, a −C 2 H 4 OH group,
【式】基又は[Formula] Group or
【式】基を表わし、[Formula] represents a group,
【式】基の
位置は６又は７位である。）で表わされる水溶性
ジスアゾ化合物又はこの銅錯塩化合物に関する。
本発明の化合物はセルロース繊維の染色にも用
いることが出来るが、主な使用目的は偏光膜の製
造用である。従来、偏光膜用の着色剤としてはヨ
ウ素が用いられているが、耐昇華性が劣り、熱安
定性が低いので使用される分野が制限されてい
た。本発明の目的は耐久性の優れた偏光膜着色用
の化合物を提供することにある。
本発明の水溶性ジスアゾ化合物は一般的には次
のように製造される。
即ち式
で示される化合物を常法によりジアゾ化し、
式
（式（）中ＸおよびＹは前記と同じ意味を表
わす。）
で示される化合物とカツプリングし、
式
（式（）中、ＸおよびＹは前記と同じ意味を
表わす。）
で示されるモノアゾ化合物を製造し、このものを
更にジアゾ化して式
（式（）中、R1，R2は前記と同じ意味を表
わし[Formula] The position of the group is the 6th or 7th position. ) or its copper complex salt compound. Although the compounds of the present invention can also be used to dye cellulose fibers, their main purpose is for the production of polarizing films. Conventionally, iodine has been used as a colorant for polarizing films, but its poor sublimation resistance and low thermal stability have limited the fields in which it can be used. An object of the present invention is to provide a compound for coloring a polarizing film that has excellent durability. The water-soluble disazo compound of the present invention is generally produced as follows. That is, the expression The compound represented by is diazotized by a conventional method, and the formula (X and Y in formula () represent the same meanings as above.) When coupled with a compound represented by the formula (In the formula (), X and Y represent the same meanings as above.) A monoazo compound represented by the formula is produced, and this compound is further diazotized to give the formula (In formula (), R 1 and R 2 represent the same meanings as above.
【式】は６−又は７−位に結合してい
る）で示される化合物と常法によりカツプリング
し、式（）の水溶性ジスアゾ化合物を製造す
る。更に必要に応じ硫酸銅等で処理して式（）
で示される化合物の銅錯塩化合物をえる。
式（）の化合物は通常ナトリウム塩として製
造するが、それらは遊離酸として、あるいはカリ
ウム塩、リチウム塩、アンモニウム塩、アルキル
アミン、エタノールアミン類の塩として製造する
ことが出来る。
式（）に相当する化合物の具体的な例として
はThe water-soluble disazo compound of the formula (2) is prepared by coupling with a compound represented by the formula (2) bonded at the 6- or 7-position by a conventional method. Further, if necessary, process with copper sulfate etc. to form formula ()
A copper complex salt compound of the compound represented by is obtained. Compounds of formula () are usually prepared as sodium salts, but they can also be prepared as free acids or as potassium, lithium, ammonium, alkylamine, and ethanolamine salts. A specific example of a compound corresponding to formula () is
【式】【formula】
【式】【formula】
【式】等があげられ、式（）で
示される化合物の具体的な例としては、Ｊ酸、Ｎ
−メチルＪ酸、Ｎ−２−ヒドロキシエチルＪ酸、
フエニールＪ酸、Ｎ−メチル−フエニールＪ酸、
（３又は４−カルボキシ）フエニールＪ酸、Ｎ−
メチル−（３又は４−カルボキシ）フエニ−ルＪ
酸、（３又は４−スルホ）フエニールＪ酸、Ｎ−
メチル−（３又は４−スルホ）フエニールＪ酸、
γ酸、Ｎ−メチルγ酸、Ｎ−２−ヒドロキシエチ
ルγ酸、フエニールγ酸、Ｎ−メチルフエニール
γ酸、（３又は４−カルボキシ）フエニールγ酸、
Ｎ−メチル−（３又は４−カルボキシ）フエニー
ルγ酸、（３又は４−スルホ）フエニールγ酸、
Ｎ−メチル（３又は４−スルホ）フエニ−ルγ酸
等があげられる。
本発明の化合物は通常の染色法で木綿、スフ、
ビスコース、レーヨン、紙、バルブなどのセルロ
ース基質にも良く染着するのでこれらの基質の染
色にも有用であるが、特に二色性を有する偏光膜
用着色剤として価値がある。
従来、ヨウ素を偏光素子とする偏光膜は偏光率
が高いこと、可視光全領域について光吸収性を有
していること等の理由で広く用いられているが、
堅牢性に乏しく熱あるいは光に曝露されると消色
したり昇華したりして効果が著しく低下する欠点
がある。
式（）のジスアゾ化合物又はその銅錯塩化合
物を偏光素子として用いるとこの様な欠点が解消
され、二色性と堅牢性の優れた偏光膜を得ること
が出来、従来限定されていた用途を大幅に拡大す
ることが出来る。
偏光膜製造の為の素材としてはポリビニルアル
コール、セロフアン等の水酸基をもつた合成又は
天然のポリマー又はナイロンのようなポリアミド
系樹脂又はリビニルアルコールと酢酸ビニルとの
共重合物からえられる膜等が用いられる。
次に実施例により本発明をさらに詳しく説明す
る。これらの実施例に於て部は重量により、そし
て百分率は重量による。
実施例 １
４−ニトロ−4′−アミノスチルベン−２，2′−
ジスルホン酸ソーダ57.7部を常法によりジアゾ化
し、酢酸ソーダを中和剤として使用し２−メトキ
シ−５−メチルアニリン18.7部を塩酸水溶液に溶
解したものにカツプリングする。反応が終了した
ら塩酸で酸析し過、乾燥すれば67.9部のモノア
ゾ化合物（次式）が得られる。
このモノアゾ化合物67.9部を水1700部に苛性ソ
ーダ11.7部と共に溶解し、この溶液に亜硝酸ソー
ダ10.3部を溶解する。別に水160部、35％塩酸73
部で塩酸水溶液を作り、これに前記のモノアゾ化
合物と苛性ソーダ、亜硝酸ソーダとの混合溶液を
滴下して５〜10℃でジアゾ化する。ジアゾ化が終
了したら、スルフアミン酸を加えて亜硝酸イオン
を消去する。フエニールＪ酸40.3部を10％ソーダ
灰水溶液1000部に溶解し、前記ジアゾニウム塩を
加え５〜10℃でカツプリングする。一夜撹拌後生
成した沈澱を別し乾燥すれば75.3部の次式の水
溶性ジスアゾ化合物が得られる。このジスアゾ化
合物をPH9.5の緩衝液に溶解した時のλmaxは
553nmであつた。
実施例 ２
実施例１においてフエニールＪ酸40.3部の代り
にγ酸30.5部を使用することを除いて実施例１と
同様にして69.2部の水溶性ジスアゾ化合物（次
式）を得た。
このものをPH9.5の緩衝液に溶解した時のλmax
は562nmであつた。
実施例 ３
実施例１のジスアゾ化合物75.3部を1200部の水
に溶解しCuSo4・5H2Oの20％水溶液110部、Ｎ，
Ｎ−ジエタノールアミン60部、25％アンモニア水
15部を加え95℃で８時間処理した。少量の塩酸で
この反応液をPH9.0とし液容量に対し12％の食塩
を加え生成した沈澱を別乾燥して次式で示され
る銅錯塩化合物の粉末が得られた。この染料をPH
9.5の緩衝液に溶解した時のλmaxは、598nmであ
つた。
偏光膜の製造： ドクターコーター及び送風型乾
燥機を備えたコーテイング装置を用いて製膜
したポリビニ−ルアルコールフイルムを実施
例１，２又は３で得られた化合物10ｇを10
の水に溶解してえた40℃の溶液中に1.5分間
浸漬した後流水で洗浄すると、青色に染色さ
れた膜が得られる。この膜をロール型延伸機
を用いて縦方向に3.5倍に延伸して偏光膜を
得た。この様にして得られた偏光膜の光線透
過度を測定した結果を下表に示す。Specific examples of compounds represented by formula () include J acid, N
-Methyl J acid, N-2-hydroxyethyl J acid,
Phenyl J acid, N-methyl-phenyl J acid,
(3 or 4-carboxy)phenyl J acid, N-
Methyl-(3 or 4-carboxy)phenyl J
acid, (3 or 4-sulfo)phenyl J acid, N-
methyl-(3 or 4-sulfo)phenyl J acid,
γ acid, N-methyl γ acid, N-2-hydroxyethyl γ acid, phenyl γ acid, N-methylphenyl γ acid, (3 or 4-carboxy) phenyl γ acid,
N-methyl-(3 or 4-carboxy)phenyl γ acid, (3 or 4-sulfo)phenyl γ acid,
Examples include N-methyl (3 or 4-sulfo) phenyl γ acid. The compound of the present invention can be used to dye cotton, stapler,
Since it dyes well on cellulose substrates such as viscose, rayon, paper, and bulbs, it is useful for dyeing these substrates, but it is particularly valuable as a dichroic coloring agent for polarizing films. Conventionally, polarizing films using iodine as a polarizing element have been widely used because of their high polarization rate and their ability to absorb light in the entire visible light range.
It has the disadvantage of poor fastness and decolorization or sublimation when exposed to heat or light, resulting in a significant decrease in effectiveness. By using the disazo compound of formula () or its copper complex salt compound as a polarizing element, these drawbacks can be overcome, and a polarizing film with excellent dichroism and fastness can be obtained, greatly expanding the range of uses that were previously limited. It can be expanded to. Materials for producing polarizing films include films made from synthetic or natural polymers with hydroxyl groups such as polyvinyl alcohol and cellophane, polyamide resins such as nylon, or copolymers of ribinyl alcohol and vinyl acetate. used. Next, the present invention will be explained in more detail with reference to Examples. In these examples, parts are by weight and percentages are by weight. Example 1 4-nitro-4'-aminostilbene-2,2'-
57.7 parts of sodium disulfonate are diazotized by a conventional method, and coupled with 18.7 parts of 2-methoxy-5-methylaniline dissolved in an aqueous hydrochloric acid solution using sodium acetate as a neutralizing agent. After the reaction is completed, 67.9 parts of a monoazo compound (the following formula) is obtained by acid precipitation with hydrochloric acid, filtration, and drying. 67.9 parts of this monoazo compound are dissolved in 1700 parts of water along with 11.7 parts of caustic soda, and 10.3 parts of sodium nitrite are dissolved in this solution. Separately 160 parts of water, 73 parts of 35% hydrochloric acid
An aqueous solution of hydrochloric acid is prepared in step 1, and a mixed solution of the monoazo compound, caustic soda, and sodium nitrite is added dropwise thereto to diazotize it at 5 to 10°C. After diazotization is completed, sulfamic acid is added to eliminate nitrite ions. 40.3 parts of Phenyl J acid is dissolved in 1000 parts of a 10% soda ash aqueous solution, the above diazonium salt is added thereto, and the mixture is coupled at 5 to 10°C. After stirring overnight, the precipitate formed is separated and dried to obtain 75.3 parts of a water-soluble disazo compound of the following formula. When this disazo compound is dissolved in a buffer solution of PH9.5, λmax is
It was 553nm. Example 2 69.2 parts of a water-soluble disazo compound (the following formula) was obtained in the same manner as in Example 1, except that 30.5 parts of γ acid was used instead of 40.3 parts of Phenyl J acid. λmax when this substance is dissolved in a buffer solution of PH9.5
was 562nm. Example 3 75.3 parts of the disazo compound of Example 1 was dissolved in 1200 parts of water, and 110 parts of a 20% aqueous solution of CuSo 4.5H 2 O, N,
60 parts of N-diethanolamine, 25% aqueous ammonia
15 parts were added and treated at 95°C for 8 hours. The reaction solution was adjusted to pH 9.0 with a small amount of hydrochloric acid, and 12% common salt was added to the solution volume, and the resulting precipitate was separately dried to obtain a powder of a copper complex compound represented by the following formula. This dye has a PH
λmax when dissolved in 9.5 buffer solution was 598 nm. Production of polarizing film: 10 g of the compound obtained in Example 1, 2 or 3 was added to a polyvinyl alcohol film formed using a coating device equipped with a doctor coater and a blow dryer.
A membrane dyed blue is obtained by immersing the membrane in a solution prepared by dissolving it in water at 40°C for 1.5 minutes and then washing with running water. This film was stretched 3.5 times in the longitudinal direction using a roll-type stretching machine to obtain a polarizing film. The results of measuring the light transmittance of the polarizing film thus obtained are shown in the table below.
【表】【table】
【表】
実施例 ４〜11
式（）および（）の化合物として表に示さ
れた化合物を用い実施例１〜３と同様にして製造
したジスアゾ化合物又はそれらを銅錯塩化してえ
た化合物をPH9.5の緩衝液に溶解した時のλmaxお
よびそれらの化合物を用いて実施例３と同様に偏
光膜を作製した場合のρの値を以下の表に示し
た。[Table] Examples 4 to 11 Disazo compounds produced in the same manner as in Examples 1 to 3 using the compounds shown in the table as compounds of formulas () and (), or compounds obtained by converting them into copper complex salts, were prepared at pH 9. The table below shows the λmax when dissolved in the buffer solution of No. 5 and the value of ρ when a polarizing film was prepared in the same manner as in Example 3 using these compounds.
【表】【table】
【表】
＊ ２点で同じ吸光度を示した。
実施例 12〜18
実施例１，２，３と同様に操作して表に示され
る式（），（）の化合物を用いジスアゾ化合物
を製造しPH9.5の緩衝液に溶解しそのλmaxを測定
した。
結果は次表の通りである。[Table] * Two points showed the same absorbance.
Examples 12 to 18 Disazo compounds were produced using the compounds of formulas () and () shown in the table by operating in the same manner as in Examples 1, 2, and 3, dissolved in a pH 9.5 buffer solution, and measured for its λmax. did. The results are shown in the table below.
【表】【table】
Claims (1)
メトキシ基又はエトキシ基を、Ｙはメトキシ基又
はエトキシ基を、R1は水素原子又はメチル基を、
R2は水素原子、メチル基、−C2H4OH基、
【式】【式】基又は 【式】基を表わし、【式】基の 位置は６又は７位である） で表わされる水溶性ジスアゾ化合物又はこの銅錯
塩化合物。[Claims] 1. General formula as a free acid (In formula (), X is a hydrogen atom, a methyl group,
methoxy group or ethoxy group, Y is methoxy group or ethoxy group, R 1 is hydrogen atom or methyl group,
R 2 is a hydrogen atom, a methyl group, a -C 2 H 4 OH group,
A water-soluble disazo compound or a copper complex salt compound thereof, represented by [Formula] [Formula] group or [Formula] group, and the position of [Formula] group is the 6th or 7th position.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1753583A JPS59145255A (en) | 1983-02-07 | 1983-02-07 | Water-soluble disazo compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1753583A JPS59145255A (en) | 1983-02-07 | 1983-02-07 | Water-soluble disazo compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59145255A JPS59145255A (en) | 1984-08-20 |
| JPH0261988B2 true JPH0261988B2 (en) | 1990-12-21 |
Family
ID=11946612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1753583A Granted JPS59145255A (en) | 1983-02-07 | 1983-02-07 | Water-soluble disazo compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59145255A (en) |
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|---|---|---|---|---|
| JPS6289907A (en) * | 1985-06-19 | 1987-04-24 | Sumitomo Bakelite Co Ltd | Transparent conductive film united with polarizing film |
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| US5659020A (en) * | 1994-09-16 | 1997-08-19 | Sumitomo Chemical Company, Limited | Tetrakisazo compound and a polarizing film containing the same |
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| KR100357909B1 (en) * | 2000-05-23 | 2002-10-25 | 신화오플라주식회사 | Process for the preparation of disazo compound |
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| CA2586123A1 (en) | 2004-11-24 | 2006-06-01 | Nippon Kayaku Kabushiki Kaisha | Azo compounds and dye-type polarizing films or plates containing the same |
| JP5374940B2 (en) * | 2007-07-09 | 2013-12-25 | 三菱化学株式会社 | Anisotropic membrane compounds |
| JP6107352B2 (en) * | 2013-04-12 | 2017-04-05 | 三菱化学株式会社 | Dye for anisotropic dye film, composition containing the dye, anisotropic dye film and polarizing element |
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| CN117412995A (en) | 2021-06-24 | 2024-01-16 | 积水化学工业株式会社 | Polyvinyl alcohol resin, polyvinyl acetal resin, method for producing polyvinyl alcohol resin, and method for producing polyvinyl acetal resin |
-
1983
- 1983-02-07 JP JP1753583A patent/JPS59145255A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017146212A1 (en) | 2016-02-26 | 2017-08-31 | 日本化薬株式会社 | Azo compound or salt thereof, and polarizing film containing same |
| JPWO2019117123A1 (en) * | 2017-12-13 | 2021-01-07 | 日本化薬株式会社 | Polarizing elements for the visible and infrared regions, and polarizing plates |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59145255A (en) | 1984-08-20 |
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