JPH0232301B2 - JISUAZOSENRYONOSEIZOHO - Google Patents
JISUAZOSENRYONOSEIZOHOInfo
- Publication number
- JPH0232301B2 JPH0232301B2 JP19600581A JP19600581A JPH0232301B2 JP H0232301 B2 JPH0232301 B2 JP H0232301B2 JP 19600581 A JP19600581 A JP 19600581A JP 19600581 A JP19600581 A JP 19600581A JP H0232301 B2 JPH0232301 B2 JP H0232301B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen atom
- represented
- general formula
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 26
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000004744 fabric Substances 0.000 description 18
- 239000000835 fiber Substances 0.000 description 15
- -1 disazo compound Chemical class 0.000 description 14
- 229920000728 polyester Polymers 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明はジスアゾ染料の新規な製造方法に関す
るものである。
ヘテロ環含有ジスアゾ染料は耐光堅牢度等の諸
堅牢度がすぐれており、特に、モル分子吸光係数
が高く、カラーバリユーも大きいために、ポリエ
ステル繊維用ネービー色分散染料として注目され
ている。
ヘテロ環含有ジスアゾ染料の製造法については
すでに数多くの報告がなされている（たとえば特
開昭51−41734、特開昭53−33225など）が、この
ような従来知られている方法により製造すると満
足のできる収率と特に高い純度を達成することが
困難であつた。
本発明者らは上記ヘテロ環含有ジスアゾ染料を
高収率、高純度を得る方法について鋭意検討した
結果、ヘテロ環含有アミンのジアゾ成分のジアゾ
ニウム塩とアルキルアミノ基のパラ位にカルボキ
シル基、ヒドロキシメチル基、ホルミル基、アセ
チル基またはスルホン酸基等の脱離基を有するア
ミン類とカツプリングさせることにより、非常に
高い収率で高純度のジスアゾ染料が得られること
を見い出し本発明を達成したもおである。
すなわち、本発明の目的は一般式〔〕
（式中、R1，R2およびR3は水素原子、ハロゲ
ン原子、ニトロ基、シアノ基、トリフルオロメチ
ル基、低級アルキル基、低級アルコキシ基、低級
アルコキシカルボニル基、低級アルキルスルホニ
ル基、Ｎ，Ｎ−ジ低級アルキルスルフアモイル基
または低級アシルアミノ基を表わし、Ａは
The present invention relates to a novel method for producing disazo dyes. Heterocycle-containing disazo dyes have excellent light fastness and other fastness properties, and in particular, have a high molar molecular extinction coefficient and a large color value, so they are attracting attention as navy-colored disperse dyes for polyester fibers. Many reports have already been made on methods for producing heterocycle-containing disazo dyes (e.g., JP-A-51-41734, JP-A-53-33225, etc.), but production using such conventionally known methods is not satisfactory. It has been difficult to achieve reasonable yields and particularly high purity. As a result of intensive studies on methods for obtaining high yield and high purity of the above-mentioned heterocycle-containing disazo dye, the present inventors found that a diazonium salt of the diazo component of a heterocycle-containing amine and a carboxyl group at the para position of the alkylamino group, hydroxymethyl The present invention has been achieved by discovering that a highly purified disazo dye can be obtained in an extremely high yield by coupling it with an amine having a leaving group such as a sulfonic acid group, a formyl group, an acetyl group, or a sulfonic acid group. It is. That is, the purpose of the present invention is to solve the general formula [] (In the formula, R 1 , R 2 and R 3 are a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, N, N-dilower alkylsulfamoyl group or lower acylamino group, A is
【式】または[expression] or
【式】を表わし、
R7は水素原子、フエニル基、低級アルキル基ま
たは低級アルコキシカルボニルアルキル基を表わ
し、R8はシアノ基、ニトロ基、低級アルコキシ
カルボニル基、低級アルキルスルホニル基、カル
バモイル基、Ｎ−低級アルキルカルバモイル基ま
たはＮ，Ｎ−ジ低級アルキルカルバモイル基を表
わし、R9は水素原子；低級アルキル基；低級ア
ルキル基、低級アルコキシ基、ハロゲン原子もし
くはアシル基で置換されていてもよいフエニル基
またはチエニル基を表わし、R4は水素原子、ヒ
ドロキシル基、メチル基、塩素原子またはアシル
アミノ基を表わし、R5およびR6は水素原子、置
換もしくは非置換のアルキル基、シクロヘキシル
基、アルケニル基またはアリール基を表わす。）
で示されるジスアゾ染料の新規な製造方法を提供
することにあり、この目的は一般式〔〕
（式中、R1，R2，R3およびＡは前記定義に同
じ。）で示されるアミンをジアゾ化し、一般式
〔〕
（式中、Ｘはカルボキシル基、ヒドロキシメチ
ル基、ホルミル基、アセチル基、またはスルホン
酸基を表わし、R4，R5およびR6は前記定義に同
じ。）
で示されるアミンとカツプリングさせることによ
り容易に達成し得る。
以下に本発明を詳細に説明する。
本発明方法においてジアゾ成分として用いられ
る一般式〔〕で示されるアミンの具体例を下記
に示す。
カツプリング成分として用いられる一般式
〔〕で示されるアミンの具体例を下記表−１に
示す。[Formula], R 7 represents a hydrogen atom, phenyl group, lower alkyl group, or lower alkoxycarbonyl alkyl group, R 8 represents a cyano group, nitro group, lower alkoxycarbonyl group, lower alkylsulfonyl group, carbamoyl group, N -represents a lower alkylcarbamoyl group or an N,N-dilower alkylcarbamoyl group, R 9 is a hydrogen atom; a lower alkyl group; a phenyl group optionally substituted with a lower alkyl group, a lower alkoxy group, a halogen atom or an acyl group or a thienyl group, R 4 represents a hydrogen atom, a hydroxyl group, a methyl group, a chlorine atom or an acylamino group, and R 5 and R 6 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group or an aryl group. represents a group. ) The purpose is to provide a new method for producing a disazo dye represented by the general formula [] (In the formula, R 1 , R 2 , R 3 and A are the same as defined above.) The amine represented by the general formula [] (In the formula, X represents a carboxyl group, a hydroxymethyl group, a formyl group, an acetyl group, or a sulfonic acid group, and R 4 , R 5 and R 6 are the same as defined above.) easily achieved. The present invention will be explained in detail below. Specific examples of the amine represented by the general formula [] used as the diazo component in the method of the present invention are shown below. Specific examples of amines represented by the general formula [] used as coupling components are shown in Table 1 below.
【表】【table】
【表】
本発明方法によれば、一般式〔〕で示される
アミンを常法によりジアゾ化し、このジアゾ液を
水中または水と混合しうる有機溶剤（たとえばメ
タノール、エタノール等のアルコール類、ジメチ
ルホルムアミド等のＮ−アルキルホルムアミド
類、Ｎ−メチルピロリドン等のＮ−アルキルピロ
リドン類、アセトン、メチルエチルケトン等のケ
トン類など）と水との混合物中の一般式〔〕で
示されるパラ位に脱離基を有するアミン類（カツ
プリング成分）の溶液に加え、必要に応じてカツ
プリング反応を容易にするために混合物のPHを調
節し、得られるジスアゾ染料を単離することによ
つて高収率で高純度のジスアゾ染料を得ることが
できる。
本発明方法により得られる一般式〔〕で示さ
れるジスアゾ染料はポリエステル系繊維をはじめ
としてポリアクリロニトリル系繊維、ポリウレタ
ン系繊維、トリアセテート系繊維、シアセテート
系繊維等の合成ないしは半合成高分子物質よりな
る合成繊維類を良好な諸堅牢度をもつてネービー
色に染色することができる。
次に本発明を実施例により更に具体的に説明す
るが、本発明はその要旨を越えない限り以下の実
施例に限定されるものではない。
実施例 １
98％硫酸28.8mlに亜硫酸ナトリウム2.0ｇを加
え55℃に加温して溶解させニトロシル硫酸を調製
した。この反応液を冷却し、５〜10℃で酢酸9.12
ｇを添加し、引続して０〜５℃で40％硫酸を滴下
した。
更に下記式
で示される化合物4.56ｇを添加し、−２℃〜０℃
で２時間撹拌したのち尿素1.0ｇを加えジアゾ液
とした。
一方、下記式
で示される化合物4.08ｇをメタノール500mlに溶
解させ、カツプリング液とした。
このカツプリング溶液に０〜５℃にてジアゾ液
を30分を要して添加し、さらに５時間撹拌した。
析出した結晶を別したのち、水洗および乾燥を
行ない、
下記式
で示されるジスアゾ化合物7.93ｇを得た。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は605nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色（130℃）を行なつたところ、ネ
ービー色の染布が得られた。得られた染布の耐光
堅牢度は良好であつた。
実施例 ２
実施例１と同様の方法で式〔〕のモノアゾ化
合物からジアゾ液を調製した。
一方、下記式
で示される化合物4.78ｇを３％硫酸500mlに溶解
させ、カツプリング液とした。
このカツプリング液に０〜５℃にてジアゾ液を
30分を要して添加し、さらに８時間撹拌した。析
出した結晶を別したのち、水洗および乾燥を行
ない、下記式
で示されるジスアゾ化合物8.62ｇを得た。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は620nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色（130℃）を行なつたところ、ネ
ービー色の染布が得られた。得られた染布の耐光
堅牢度は良好であつた。
実施例 ３
実施例１と同様の方法で式〔〕のモノアゾ化
合物からジアゾ液を調製した。
一方、下記式
で示される化合物3.28ｇを水300mlに溶解させ、
カツプリング液とした。
このカツプリング液に０〜５℃にてジアゾ液を
20分を要して滴下し、さらに８時間撹拌した。析
出した結晶を別した後、水洗および乾燥を行な
い、下記式
で示されるジスアゾ化合物7.66ｇを得た。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は638nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色（130℃）を行なつたところ、ネ
ービー色の染布が得られた。得られた染布の耐光
堅牢度は良好であつた。
実施例 ４
カツプリング成分として下記式
で示される化合物3.26ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶6.84ｇが得られた。
このジスアゾ化合物を最大吸収波長（80容量％
アセトン水溶液中）は625nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 ５
カツプリング成分として下記式
で示される化合物6.18ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶9.66ｇが得られた。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は605nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 ６
ジアゾ成分として下記式
で示される化合物4.36ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶7.66ｇが得られた。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は585nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 ７
ジアゾ成分として下記式
で示される化合物5.60ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶8.74ｇが得られた。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は585nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 ８
ジアゾ成分として下記式
で示される化合物5.72ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶8.85ｇが得られた。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は600nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 ９
ジアゾ成分として下記式
で示される化合物5.46ｇを使用したこと以外は実
施例１と同様に実験を行なつた。
その結果、下記式
で示される染料の黒色結晶8.70ｇが得られた。
このジスアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は630nmであり、高速液体ク
ロマトグラフイーによる純度分析で高い純度数値
を示した。
本実施例で得られた染料を用いてポリエステル
繊維の高温染色を行なつたところ、ネービー色の
染布が得られた。得られた染布の耐光堅牢度は良
好であつた。
実施例 10
カツプリング成分として下記表−２で示される
化合物を使用したこと以外は実施例１と同様に実
験を行ない、同表に示すジスアゾ染料を得、ポリ
エステル繊維を染色し、同表に示す色調の染色物
を得た。[Table] According to the method of the present invention, the amine represented by the general formula [] is diazotized by a conventional method, and the diazo solution is converted into water or an organic solvent miscible with water (for example, alcohols such as methanol and ethanol, dimethylformamide, etc.). N-alkylformamides such as N-alkylpyrrolidones such as N-methylpyrrolidone, ketones such as acetone and methyl ethyl ketone) and water, by adding a leaving group to the para position represented by the general formula []. By adding the amines (coupling component) to the solution, adjusting the pH of the mixture as necessary to facilitate the coupling reaction, and isolating the resulting disazo dye, high yield and high purity dyes can be obtained. Disazo dyes can be obtained. The disazo dye represented by the general formula [ ] obtained by the method of the present invention is made of synthetic or semi-synthetic polymeric substances such as polyester fibers, polyacrylonitrile fibers, polyurethane fibers, triacetate fibers, cyacetate fibers, etc. Synthetic fibers can be dyed navy blue with good fastness properties. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 Nitrosyl sulfuric acid was prepared by adding 2.0 g of sodium sulfite to 28.8 ml of 98% sulfuric acid and dissolving it by heating to 55°C. This reaction solution was cooled and acetic acid 9.12
g was added, followed by dropwise addition of 40% sulfuric acid at 0-5°C. Furthermore, the following formula Add 4.56g of the compound shown and heat from -2℃ to 0℃
After stirring for 2 hours, 1.0 g of urea was added to prepare a diazo solution. On the other hand, the following formula 4.08 g of the compound represented by was dissolved in 500 ml of methanol to prepare a coupling liquid. The diazo solution was added to this coupling solution over a period of 30 minutes at 0 to 5°C, and the mixture was further stirred for 5 hours.
After separating the precipitated crystals, they were washed with water and dried, and the following formula was obtained. 7.93 g of a disazo compound represented by was obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 605 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature (130° C.) using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 2 A diazo liquid was prepared from the monoazo compound of formula [] in the same manner as in Example 1. On the other hand, the following formula 4.78 g of the compound represented by was dissolved in 500 ml of 3% sulfuric acid to prepare a coupling liquid. Add diazo liquid to this coupling liquid at 0-5℃.
The mixture was added over 30 minutes and stirred for an additional 8 hours. After separating the precipitated crystals, they were washed with water and dried, and the following formula was obtained. 8.62 g of a disazo compound represented by was obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 620 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature (130° C.) using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 3 A diazo liquid was prepared from the monoazo compound of formula [] in the same manner as in Example 1. On the other hand, the following formula Dissolve 3.28g of the compound shown in 300ml of water,
It was used as a coupling liquid. Add diazo liquid to this coupling liquid at 0-5℃.
The mixture was added dropwise over 20 minutes and further stirred for 8 hours. After separating the precipitated crystals, they were washed with water and dried, and the following formula was obtained. 7.66 g of a disazo compound represented by was obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 638 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature (130° C.) using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 4 The following formula as the coupling component An experiment was carried out in the same manner as in Example 1, except that 3.26 g of the compound represented by was used. As a result, the following formula 6.84 g of black crystals of the dye represented by were obtained. Maximum absorption wavelength (80% by volume) of this disazo compound
(in acetone aqueous solution) was 625 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 5 The following formula as the coupling component An experiment was carried out in the same manner as in Example 1, except that 6.18 g of the compound represented by was used. As a result, the following formula 9.66 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 605 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 6 The following formula as the diazo component An experiment was carried out in the same manner as in Example 1, except that 4.36 g of the compound represented by was used. As a result, the following formula 7.66 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 585 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 7 The following formula as the diazo component An experiment was carried out in the same manner as in Example 1, except that 5.60 g of the compound represented by was used. As a result, the following formula 8.74 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 585 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 8 The following formula as the diazo component An experiment was carried out in the same manner as in Example 1, except that 5.72 g of the compound represented by was used. As a result, the following formula 8.85 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 600 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 9 The following formula as the diazo component An experiment was carried out in the same manner as in Example 1, except that 5.46 g of the compound represented by was used. As a result, the following formula 8.70 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this disazo compound (80% by volume)
(in acetone aqueous solution) was 630 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fibers were dyed at high temperature using the dye obtained in this example, a navy-colored dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 10 An experiment was carried out in the same manner as in Example 1, except that the compounds shown in Table 2 below were used as coupling components, and the disazo dyes shown in the table were obtained, and polyester fibers were dyed to produce the colors shown in the table. A dyed product was obtained.
【表】【table】
【表】【table】
【表】
実施例 11
ジアゾ成分として下記表−３で示される化合物
を使用したこと以外は実施例１と同様に実験を行
ない、同表に示すジスアゾ染料を得、ポリエステ
ル繊維を染色し、同表に示す色調の染色物を得
た。[Table] Example 11 An experiment was conducted in the same manner as in Example 1, except that the compounds shown in Table 3 below were used as the diazo component, and the disazo dyes shown in the table were obtained, and polyester fibers were dyed. A dyed product having the color tone shown in was obtained.
【表】【table】
Claims (1)
ン原子、ニトロ基、シアノ基、トリフルオロメチ
ル基、低級アルキル基、低級アルコキシ基、低級
アルコキシカルボニル基、低級アルキルスルホニ
ル基、Ｎ，Ｎ−ジ低級アルキルスルフアモイル基
または低級アシルアミノ基を表わし、 Ａは【式】または【式】を 表わし、R7は水素原子、フエニル基、低級アル
キル基または低級アルコキシカルボニルアルキル
基を表わし、R8はシアノ基、ニトロ基、低級ア
ルコキシカルボニル基、低級アルキルスルホニル
基、カルバモイル基、Ｎ−低級アルキルカルバモ
イル基またはＮ，Ｎ−ジ低級アルキルカルバモイ
ル基を表わし、R9は水素原子；低級アルキル
基；低級アルキル基、低級アルコキシ基、ハロゲ
ン原子もしくはアシル基で置換されていてもよい
フエニル基またはチエニル基を表わす。） で示されるアミンをジアゾ化し、一般式〔〕 （式中、Ｘはカルボキシル基、ヒドロキシメチ
ル基、ホルミル基、アセチル基、またはスルホン
酸基を表わし、R4は水素原子、ヒドロキシル基、
メチル基、塩素原子またはアシルアミノ基を表わ
し、R5およびR6は水素原子、置換もしくは非置
換のアルキル基、シクロヘキシル基、アルケニル
基またはアリール基を表わす。）で示されるアニ
リン類とカツプリングさせることを特徴とする一
般式〔〕 （式中、R1，R2，R3，Ａ，R4，R5およびR6は
前記定義に同じ。） で示されるジスアゾ染料の製造法。[Claims] 1. General formula [] (In the formula, R 1 , R 2 and R 3 are a hydrogen atom, a halogen atom, a nitro group, a cyano group, a trifluoromethyl group, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, N, N-dilower alkylsulfamoyl group or lower acylamino group, A represents [Formula] or [Formula], R 7 represents a hydrogen atom, phenyl group, lower alkyl group or lower alkoxycarbonyl alkyl group, R 8 represents a cyano group, nitro group, lower alkoxycarbonyl group, lower alkylsulfonyl group, carbamoyl group, N-lower alkylcarbamoyl group or N,N-dilower alkylcarbamoyl group, R 9 is a hydrogen atom; lower alkyl group; Represents a lower alkyl group, lower alkoxy group, phenyl group or thienyl group which may be substituted with a halogen atom or an acyl group.) An amine represented by the following formula is diazotized to form the general formula [] (In the formula, X represents a carboxyl group, hydroxymethyl group, formyl group, acetyl group, or sulfonic acid group, and R 4 represents a hydrogen atom, a hydroxyl group,
It represents a methyl group, a chlorine atom or an acylamino group, and R 5 and R 6 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, an alkenyl group or an aryl group. ) General formula characterized by coupling with anilines represented by [] (In the formula, R 1 , R 2 , R 3 , A, R 4 , R 5 and R 6 are the same as defined above.) A method for producing a disazo dye represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19600581A JPH0232301B2 (en) | 1981-12-05 | 1981-12-05 | JISUAZOSENRYONOSEIZOHO |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19600581A JPH0232301B2 (en) | 1981-12-05 | 1981-12-05 | JISUAZOSENRYONOSEIZOHO |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5896655A JPS5896655A (en) | 1983-06-08 |
| JPH0232301B2 true JPH0232301B2 (en) | 1990-07-19 |
Family
ID=16350636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19600581A Expired - Lifetime JPH0232301B2 (en) | 1981-12-05 | 1981-12-05 | JISUAZOSENRYONOSEIZOHO |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0232301B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066674B2 (en) * | 1986-04-21 | 1994-01-26 | 合成染料技術研究組合 | Disazo compound and dyeing method using the same |
| KR0152089B1 (en) * | 1990-03-19 | 1998-10-01 | 미우라 아끼라 | Metal chelate compound and optical recording medium comprising the same |
| JP4596857B2 (en) * | 2003-09-24 | 2010-12-15 | 富士フイルム株式会社 | Water-based ink and ink jet recording ink |
-
1981
- 1981-12-05 JP JP19600581A patent/JPH0232301B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5896655A (en) | 1983-06-08 |
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