JPH0313266B2 - - Google Patents
Info
- Publication number
- JPH0313266B2 JPH0313266B2 JP4061482A JP4061482A JPH0313266B2 JP H0313266 B2 JPH0313266 B2 JP H0313266B2 JP 4061482 A JP4061482 A JP 4061482A JP 4061482 A JP4061482 A JP 4061482A JP H0313266 B2 JPH0313266 B2 JP H0313266B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- optionally substituted
- hydrogen atom
- nitro
- 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
- -1 cyclohexylthio group Chemical group 0.000 claims description 17
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=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
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000004744 fabric Substances 0.000 description 18
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 13
- 239000000835 fiber Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 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
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 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
- 238000007086 side reaction Methods 0.000 description 1
- 235000010288 sodium nitrite 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
本発明はモノアゾ染料の新規な製造法に関する
ものである。
本発明者らはモノアゾ染料を高収率・高純度で
得る方法について鋭意検討した結果、アミン類の
ジアゾニウム塩とジフエニルメタン系のアミン類
とカツプリングさせた場合、副反応が抑制される
ため非常に高い収率で高純度のモノアゾ染料が得
られることを見い出し、本発明を達成したもので
ある。
すなわち、本発明の目的は一般式〔〕
（式中、Ｄは
The present invention relates to a novel method for producing monoazo dyes. The inventors of the present invention have conducted intensive studies on methods for obtaining monoazo dyes in high yield and high purity. As a result, when coupling diazonium salts of amines with diphenylmethane-based amines, side reactions are suppressed, resulting in extremely high yields. The present invention was achieved by discovering that a monoazo dye with high yield and purity can be obtained. That is, the purpose of the present invention is to solve the general formula [] (In the formula, D is
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】又 は【Formula】Also teeth
【式】を表わし、R1は水素
原子、シアノ基、ニトロ基、ハロゲン原子、トリ
フルオロメチル基、チオシアナト基；置換されて
いてもよいアルキル基、アルコキシ基、アルキル
スルホニル基、アルコキシカルボニル基、カルバ
モイル基を表わし、R2はアルキル基、アルコキ
シ基、シクロヘキシルチオ基、トリフルオロメチ
ル基、ニトロ基；置換されていてもよいアルキル
チオ基、ニトロ基で置換されていてもよいフエニ
ルチオ基、アルキルスルホニル基、ハロゲン原子
又はフエニル基を表わし、R3は水素原子、アル
キル基、アルコキシ基、ニトロ基、シアノ基、ハ
ロゲン原子、チオシアナト基；置換されていても
よいカルバモイル基、アルコキシカルボニル基又
はアルキルスルホニル基を表わし、R4は水素原
子、シアノ基；置換されていてもよいアルキル
基、アルコキシ基又はアシル基を表わし、R5は
アルキル基、アルコキシ基、ニトロ基、アシル
基；置換されていてもよいベンゾイル基を表わ
し、ｍは１，２又は３を表わし、ｎは１又は２を
表わし、R6は水素原子、ヒドロキシル基、メチ
ル基、塩素原子又はアシルアミノ基を表わし、
R7およびR8は水素原子、シクロヘキシル基、ア
ルケニル基；置換されていてもよいアルキル基又
はフエニル基を表わす。）
で示されるモノアゾ染料の新規な製法を提供する
ことにあり、この目的は、一般式〔〕
Ｄ−NH2……〔〕
（式中、Ｄ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、R6，R7およびR8は前記定義に同じ。）
で示されるジフエニルメタン系アミン類とカツプ
リングさせることにより容易に達成される。
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〔〕で示されるアミン類の具体例を下
記に示す。[Formula] represents a hydrogen atom, a cyano group, a nitro group, a halogen atom, a trifluoromethyl group, a thiocyanato group; an optionally substituted alkyl group, an alkoxy group, an alkylsulfonyl group, an alkoxycarbonyl group, a carbamoyl group. represents a group, R 2 is an alkyl group, an alkoxy group, a cyclohexylthio group, a trifluoromethyl group, a nitro group; an optionally substituted alkylthio group, a phenylthio group optionally substituted with a nitro group, an alkylsulfonyl group; represents a halogen atom or a phenyl group; R 3 represents a hydrogen atom, an alkyl group, an alkoxy group, a nitro group, a cyano group, a halogen atom, a thiocyanato group; an optionally substituted carbamoyl group, an alkoxycarbonyl group, or an alkylsulfonyl group; , R 4 represents a hydrogen atom, a cyano group; an optionally substituted alkyl group, an alkoxy group, or an acyl group; R 5 represents an alkyl group, an alkoxy group, a nitro group, an acyl group; an optionally substituted benzoyl group , m represents 1, 2 or 3, n represents 1 or 2, R 6 represents a hydrogen atom, a hydroxyl group, a methyl group, a chlorine atom or an acylamino group,
R 7 and R 8 represent a hydrogen atom, a cyclohexyl group, an alkenyl group; an optionally substituted alkyl group or a phenyl group. ) The purpose of this is to provide a new method for producing a monoazo dye represented by Diazotized, general formula [] (In the formula, R 6 , R 7 and R 8 are the same as defined above.)
This can be easily achieved by coupling with diphenylmethane-based amines represented by: The present invention will be explained in detail below. Specific examples of amines represented by the general formula [] used as the diazo component in the method of the present invention are shown below.
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】
カツプリング成分として用いられる一般式
〔〕で示されるジフエニルメタン系アミン類の
具体例を下記表−１に示す。[Formula] Specific examples of diphenylmethane-based 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
示されるジフエニルメタン系アミン類（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、得られるモノアゾ染料を単離することによつ
て高収率で高純度のモノ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
れるモノ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、ジアセテート
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黄色から
青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に亜硝酸ナトリウム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、引続いて０〜５℃で40％硫酸を滴下
した。
更に下記式
で示される化合物3.38（0.02mol）ｇ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4.5（0.0125mol）ｇ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
で示されるモノアゾ化合物6.51ｇを得た。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は598nm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、青
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〔〕のアミノ化合
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7.16ｇ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
で示されるモノアゾ化合物7.19ｇを得た。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は613nm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、青
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〔〕のアミノ化合
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5.64ｇを３％硫酸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
で示されるモノアゾ化合物6.40ｇを得た。
このモノ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（130℃）を行なつたところ、青
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4.19ｇ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5.48ｇが得られた。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は615nm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、青色の染布が
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8.94ｇ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8.01ｇが得られた。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は596nm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、青色の染布が
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3.8ｇ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6.0ｇが得られた。
このモノ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、青色の染布が
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3.0ｇ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5.2ｇが得られた。
このモノ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、紫色の染布が
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4.0ｇ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6.2ｇが得られた。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は572nm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、紫色の染布が
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4.0ｇ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6.1ｇが得られた。
このモノアゾ化合物の最大吸収波長（80容量％
アセトン水溶液中）は582nm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、紫色の染布が
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
ジアゾ成分およびカツプリング成分として下記
表−４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、同表に示すモノア
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. ), adjust the pH of the mixture to facilitate the coupling reaction if necessary, and isolate the resulting monoazo dye to obtain a high yield and high purity monoazo dye. can. The monoazo 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, diacetate fibers, etc. Synthetic fibers can be dyed from yellow to 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 nitrite 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 3.38 (0.02 mol) g of the compound represented by -
After stirring for 2 hours at 2°C to 0°C, 1.0 g of urea was added to prepare a diazo solution. On the other hand, the following formula 4.5 (0.0125 mol) 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. 6.51 g of a monoazo compound represented by was obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 598 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 blue dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 2 A diazo solution was prepared from the amino compound of formula [] in the same manner as in Example 1. On the other hand, the following formula 7.16 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. 7.19 g of a monoazo compound represented by was obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 613 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 blue dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 3 A diazo solution was prepared from the amino compound of formula [] in the same manner as in Example 1. On the other hand, the following formula 5.64 g of the compound represented by was dissolved in 300 ml of 3% sulfuric acid to prepare 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. 6.40 g of a monoazo compound represented by was obtained. The maximum absorption wavelength of this monoazo 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 (130°C) using the dye obtained in this example, a blue 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 4.19 g of the compound represented by was used. As a result, the following formula 5.48 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 615 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 blue dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 5 The following formula as the coupling component An experiment was conducted in the same manner as in Example 1, except that 8.94 g of the compound represented by was used. As a result, the following formula 8.01 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 596 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 blue 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 3.8 g of the compound represented by was used. As a result, the following formula 6.0 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo 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 blue dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 7 The following formula as the diazo component The experiment was carried out in the same manner as in Example 1, except that 3.0 g of the compound represented by was used. As a result, the following formula 5.2 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo 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 fiber was dyed at high temperature using the dye obtained in this example, a purple dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 8 The following formula as the diazo component The experiment was conducted in the same manner as in Example 1, except that 4.0 g of the compound represented by was used. As a result, the following formula 6.2 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 572 nm, and purity analysis by high performance liquid chromatography showed a high purity value. When polyester fiber was dyed at high temperature using the dye obtained in this example, a purple dyed fabric was obtained. The dyed fabric obtained had good light fastness. Example 9 The following formula as the diazo component The experiment was conducted in the same manner as in Example 1, except that 4.0 g of the compound represented by was used. As a result, the following formula 6.1 g of black crystals of the dye represented by were obtained. The maximum absorption wavelength of this monoazo compound (80% by volume)
(in acetone aqueous solution) was 582 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 purple 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 4 below were used as the diazo component and the coupling component. Monoazo dyes shown in the same table were obtained, and polyester fibers were dyed. A dyed product with the color tone shown in was obtained.
Claims (1)
ン原子、トリフルオロメチル基、チオシアナト
基；置換されていてもよいアルキル基、アルコキ
シ基、アルキルスルホニル基、アルコキシカルボ
ニル基、カルバモイル基を表わし、R2はアルキ
ル基、アルコキシ基、シクロヘキシルチオ基、ト
リフルオロメチル基、ニトロ基；置換されていて
もよいアルキルチオ基、ニトロ基で置換されてい
てもよいフエニルチオ基、アルキルスルホニル
基、ハロゲン原子又はフエニル基を表わし、R3
は水素原子、アルキル基、アルコキシ基、ニトロ
基、シアノ基、ハロゲン原子、チオシアナト基；
置換されていてもよいカルバモイル基、アルコキ
シカルボニル基又はアルキルスルホニル基を表わ
し、R4は水素原子、シアノ基；置換されていて
もよいアルキル基、アルコキシ基又はアシル基を
表わし、R5はアルキル基、アルコキシ基、ニト
ロ基、アシル基；置換されていてもよいベンゾイ
ル基を表わし、ｍは１，２又は３を表わし、ｎは
１又は２を表わす。） で示されるアミン類をジアゾ化し、一般式〔〕 （式中、R6は水素原子、ヒドロキシル基、メ
チル基、塩素原子又はアシルアミノ基を表わし、
R7およびR8は水素原子、シクロヘキシル基、ア
ルケニル基；置換されていてもよいアルキル基又
はフエニル基を表わす。） で示されるジフエニルメタン系アミン類とカツプ
リングさせることを特徴とする一般式〔〕 （式中、Ｄ，R6，R7およびR8は前記定義に同
じ。） で示されるモノアゾ染料の製造法[Claims] 1 General formula [] D-NH 2 ... [] (wherein, D is [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] Formula] [Formula] or [Formula], R 1 is a hydrogen atom, a cyano group, a nitro group, a halogen atom, a trifluoromethyl group, a thiocyanato group; an optionally substituted alkyl group, an alkoxy group, an alkylsulfonyl group , an alkoxycarbonyl group, or a carbamoyl group, and R 2 is an alkyl group, an alkoxy group, a cyclohexylthio group, a trifluoromethyl group, or a nitro group; an optionally substituted alkylthio group, or a phenylthio optionally substituted with a nitro group group, alkylsulfonyl group, halogen atom or phenyl group, R 3
is a hydrogen atom, an alkyl group, an alkoxy group, a nitro group, a cyano group, a halogen atom, a thiocyanato group;
Represents an optionally substituted carbamoyl group, alkoxycarbonyl group or alkylsulfonyl group, R 4 is a hydrogen atom or a cyano group; represents an optionally substituted alkyl group, alkoxy group or acyl group, R 5 is an alkyl group , alkoxy group, nitro group, acyl group; represents an optionally substituted benzoyl group, m represents 1, 2 or 3, and n represents 1 or 2. ) by diazotizing the amines represented by the general formula [] (In the formula, R 6 represents a hydrogen atom, a hydroxyl group, a methyl group, a chlorine atom or an acylamino group,
R 7 and R 8 represent a hydrogen atom, a cyclohexyl group, an alkenyl group; an optionally substituted alkyl group or a phenyl group. ) A general formula characterized by coupling with diphenylmethane amines represented by [] (In the formula, D, R 6 , R 7 and R 8 are the same as defined above.) Method for producing a monoazo dye represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4061482A JPS58157863A (en) | 1982-03-15 | 1982-03-15 | Production of monoazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4061482A JPS58157863A (en) | 1982-03-15 | 1982-03-15 | Production of monoazo dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58157863A JPS58157863A (en) | 1983-09-20 |
| JPH0313266B2 true JPH0313266B2 (en) | 1991-02-22 |
Family
ID=12585399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4061482A Granted JPS58157863A (en) | 1982-03-15 | 1982-03-15 | Production of monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58157863A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59204659A (en) * | 1983-05-04 | 1984-11-20 | Casio Comput Co Ltd | Dichroic dye for liquid crystal |
| DE3622136A1 (en) * | 1986-07-02 | 1988-01-07 | Basf Ag | THIENOTHIOPHENE DYES |
| US5194598A (en) * | 1987-10-24 | 1993-03-16 | Bayer Aktiengesellschaft | Azo dyestuffs in which the coupling component contains an N,N-bis(alkoxy carbonylalkyl) substituent |
| EP0518133B1 (en) * | 1991-06-11 | 1996-04-10 | DyStar Japan Ltd. | Monoazodye |
| KR960031548A (en) * | 1995-02-20 | 1996-09-17 | 고사이 아키오 | Method for dyeing or printing monoazo compounds and hydrophobic fiber materials using the same |
| JPH09124966A (en) * | 1995-10-30 | 1997-05-13 | Daisutaa Japan Kk | Blue disperse dye mixture |
| KR100492051B1 (en) * | 1996-07-08 | 2005-09-12 | 스미또모 가가꾸 가부시키가이샤 | Dyeing or printing of monoazo compounds and hydrophobic fibers using them |
| DE10028686A1 (en) | 2000-06-09 | 2001-12-13 | Dystar Textilfarben Gmbh & Co | New hydroxypyridone methide azo dyes, useful in e.g. dyeing and printing hydrophobic fibers, ink-jet printing and color filters |
| CN104087016B (en) * | 2014-06-05 | 2016-05-04 | 浙江龙盛集团股份有限公司 | A kind of disperse dye composition, disperse dyes goods and application thereof |
| CN114014822A (en) * | 2021-11-22 | 2022-02-08 | 江苏恒盛药业有限公司 | Method for preparing disperse blue 360 by using microchannel reaction technology |
| CN116515317A (en) * | 2023-04-25 | 2023-08-01 | 宁夏保隆科技有限公司 | Preparation method of disperse blue |
-
1982
- 1982-03-15 JP JP4061482A patent/JPS58157863A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58157863A (en) | 1983-09-20 |
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