JPS6353230B2 - - Google Patents
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- Publication number
- JPS6353230B2 JPS6353230B2 JP59034022A JP3402284A JPS6353230B2 JP S6353230 B2 JPS6353230 B2 JP S6353230B2 JP 59034022 A JP59034022 A JP 59034022A JP 3402284 A JP3402284 A JP 3402284A JP S6353230 B2 JPS6353230 B2 JP S6353230B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- compound represented
- parts
- group
- 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 monoazo compound Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000000975 dye Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000985 reactive dye Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 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 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 125000001174 sulfone group Chemical group 0.000 description 4
- 210000004243 sweat Anatomy 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- KVWWLQUBOOFCCS-UHFFFAOYSA-N 1-ethylsulfonylethane;sulfuric acid Chemical group OS(O)(=O)=O.CCS(=O)(=O)CC KVWWLQUBOOFCCS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229940001496 tribasic sodium phosphate Drugs 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- GYFZMCLUPHXUDV-UHFFFAOYSA-N 2-ethoxy-5-methylaniline Chemical compound CCOC1=CC=C(C)C=C1N GYFZMCLUPHXUDV-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】
本発明は新規なモノアゾ化合物およびその製造
方法に関する。更に詳しくは、本発明は繊維材
料、特にセルロース繊維材料を黄色に染色するに
適したモノアゾ化合物およびその製造方法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel monoazo compound and a method for producing the same. More particularly, the present invention relates to a monoazo compound suitable for dyeing fibrous materials, particularly cellulosic fibrous materials, yellow, and a method for producing the same.
β−スルフアートエチルスルホン基を有する染
料がいわゆるビニルスルホン型反応染料として繊
維材料の染色に適用されることは公知である。し
かし、β−スルフアートエチルスルホン基を有す
るアゾ系の黄色反応染料による染色物は、一般に
塩素堅牢度が低く、水道水に含まれる塩素による
退色現象がしばしば問題となつており、そのため
塩素堅牢度のすぐれた黄色反応染料の出現が強く
要望されていた。 It is known that dyes having a β-sulfatoethyl sulfone group can be applied as so-called vinyl sulfone type reactive dyes for dyeing textile materials. However, dyeings made with azo-based yellow reactive dyes having a β-sulfatoethyl sulfone group generally have low chlorine fastness, and fading due to chlorine contained in tap water is often a problem. There has been a strong demand for a yellow reactive dye with excellent strength.
β−スルフアートエチルスルホン基と異なるも
う一つの代表的な反応基としてモノクロルトリア
ジニル基を反応基とする黄色染料も知られている
が、これらの反応染料は、一般に染色温度に高温
を要し、また吸尽染色適性に欠けるため捺染用に
使用されるにすぎず、更に、得られた染色物の酸
安定性が低いという欠点を有しているため、実用
的には決して充分とは言えなかつた。このような
ことから本発明者らは、特に塩素堅牢度のすぐれ
た黄色のビニルスルホン型反応染料を求めて鋭意
検討を行なつた結果、反応基としてβ−スルフア
ートエチルスルホン基と、モノクロルトリアジニ
ル基を有する特定のモノアゾ化合物がすぐれた塩
素堅牢度の黄色の染色物を与えることを見い出し
た。また、かゝる特定のモノアゾ化合物は前記の
ようなモノクロルトリアジニル基を有する反応性
染料の欠点をも解消できることを見い出した。 Yellow dyes with a monochlorotriazinyl group as another typical reactive group different from the β-sulfatoethyl sulfone group are also known, but these reactive dyes generally require high dyeing temperatures. In addition, it is only used for textile printing because it lacks exhaust dyeing suitability, and furthermore, it has the disadvantage of low acid stability of the dyed product obtained, so it is never sufficient for practical use. I couldn't say it. For these reasons, the present inventors conducted extensive research in search of a yellow vinyl sulfone type reactive dye with particularly excellent chlorine fastness. It has been found that certain monoazo compounds containing a lutriazinyl group give yellow dyeings of excellent chlorine fastness. It has also been found that such a specific monoazo compound can overcome the drawbacks of reactive dyes having a monochlorotriazinyl group as described above.
すなわち、本発明によつて、遊離酸の形で下記
一般式（）
（式中、Ｒはメトキシ基またはエトキシ基、X1、
X2はそれぞれ水素、メチル基またはメトキシ基
を表わす。）
で示されるモノアゾ化合物、および２−アミノナ
フタレン−４，８−ジスルホン酸をジアゾ化し、
一般式（）
（式中、Ｒは前記の意味を有する。）
で示されるトルイジン化合物とカツプリングさせ
て一般式（）
（式中、Ｒは前記の意味を有する。）
で示されるアミノモノアゾ化合物を得、これと塩
化シアヌルおよび一般式（）または（）
（式中、X1、X2は前記の意味を有する。）
で示されるアニリン化合物を任意の順序で縮合さ
せ、一般式（）で示されるアニリン化合物を用
いた場合は、次いで硫酸エステル化することを特
徴とする前記一般式（）で示されるモノアゾ化
合物の製造方法が提供される。 That is, according to the present invention, in the form of a free acid, the following general formula () (In the formula, R is a methoxy group or an ethoxy group ,
X 2 each represents hydrogen, a methyl group or a methoxy group. ) and 2-aminonaphthalene-4,8-disulfonic acid are diazotized,
General formula () (In the formula, R has the above-mentioned meaning.) Coupled with a toluidine compound represented by the general formula () (In the formula, R has the above-mentioned meaning.) An aminomonoazo compound represented by the above formula is obtained, which is combined with cyanuric chloride and the general formula () or (). (In the formula, X 1 and X 2 have the above-mentioned meanings.) The aniline compounds represented by the formula (2) are condensed in any order, and when the aniline compound represented by the general formula () is used, it is then sulfuric acid esterified. There is provided a method for producing a monoazo compound represented by the general formula (), characterized in that:
前記一般式（）で示されるモノアゾ化合物
は、優れた染料特性を有し繊維材料、特に木綿、
麻、ビスコース人絹、ビスコーススフ等の天然あ
るいは再生セルロース繊維材料の染色に好適であ
り、各種堅牢度、特に塩素堅牢度に優れた黄色染
色物を与えることができる。 The monoazo compound represented by the general formula () has excellent dye properties and is useful for textile materials, especially cotton,
It is suitable for dyeing natural or regenerated cellulose fiber materials such as hemp, viscose human silk, and viscose cotton, and can provide yellow dyed products with excellent fastness to various types of fastness, especially fastness to chlorine.
前記一般式（）で示されるモノアゾ化合物は
以下に述べる方法で製造することができる。 The monoazo compound represented by the general formula () can be produced by the method described below.
２−アミノナフタレン−４，８−ジスルホン酸
を常法に従つてジアゾ化し、これと一般式（）
で示されるトルイジン化合物とを通常の方法でカ
ツプリングして一般式（）で示されるアミノモ
ノアゾ化合物を得る。これと塩化シアヌルを一次
的に縮合させてジクロルトリアジニル化合物を
得、ついで一般式（）で示されるアニリン化合
物を二次的に縮合させて一般式（）で示される
モノアゾ化合物を得ることができる。 2-aminonaphthalene-4,8-disulfonic acid is diazotized according to a conventional method, and this is combined with the general formula ()
An aminomonoazo compound represented by the general formula () is obtained by coupling with a toluidine compound represented by the formula (2) using a conventional method. It is possible to firstly condense this with cyanuric chloride to obtain a dichlorotriazinyl compound, and then to secondarily condense an aniline compound represented by general formula () to obtain a monoazo compound represented by general formula (). can.
あるいは塩化シアヌルに一次的に一般式（）
で示されるアニリン化合物を縮合させ、ついで二
次的に一般式（）のアミノモノアゾ化合物を縮
合させることによつても一般式（）のモノアゾ
化合物を得ることができる。 Alternatively, cyanuric chloride can be expressed by the general formula ()
The monoazo compound of the general formula () can also be obtained by condensing the aniline compound represented by the formula (2) and then secondarily condensing the aminomonoazo compound of the general formula ().
あるいは一般式（）で示されるβ−ヒドロキ
シエチルスルホン体を前記一般式（）のアニリ
ン化合物の代わりに用いそれぞれ同様の反応を行
つた後、最後に常法に従つて硫酸中でエステル化
することにより一般式（）のモノアゾ化合物と
してもよい。 Alternatively, the β-hydroxyethyl sulfone compound represented by the general formula () can be used in place of the aniline compound of the general formula () to carry out the same reaction, and then finally esterified in sulfuric acid according to a conventional method. It may also be a monoazo compound of general formula ().
上記縮合反応はいずれの場合も公知の脱ハロゲ
ン化水素縮合の方法に従つて実施することができ
る。 In any case, the above condensation reaction can be carried out according to a known dehydrohalogenation condensation method.
上記の方法によつて製造されたモノアゾ化合物
はアルカリの作用によつて容易にスルフアートエ
チルスルホン基が変化してビニルスルホン基を有
するモノアゾ化合物とすることができる。 In the monoazo compound produced by the above method, the sulfatoethyl sulfone group can be easily changed by the action of an alkali to form a monoazo compound having a vinyl sulfone group.
このようにして得られた本発明のモノアゾ化合
物はセルローズ系繊維、例えば木綿、麻、ビスコ
ース人絹、ビスコーススフ等の天然あるいは再生
セルローズ繊維の黄色染色に有用である。 The monoazo compound of the present invention thus obtained is useful for yellow dyeing of natural or regenerated cellulose fibers such as cotton, linen, viscose human silk, and viscose cotton.
染色に際しては、吸尽法の場合、炭酸ソーダ第
三リン酸ソーダ、苛性ソーダ等の酸結合剤の存在
下に芒硝または食塩を加えた染浴で比較的低い温
度で行われる。また捺染法による染色もできる。
この際、酸結合剤の添加によつてスルフアートエ
チルスルホン基はビニルスルホン基となりセルロ
ース繊維と付加反応して染着が行われる。 In the case of the exhaust method, dyeing is carried out at a relatively low temperature in a dye bath containing Glauber's salt or common salt in the presence of an acid binder such as sodium carbonate, tribasic sodium phosphate, or caustic soda. It can also be dyed using a textile printing method.
At this time, by addition of an acid binder, the sulfate ethyl sulfone group becomes a vinyl sulfone group and undergoes an addition reaction with the cellulose fibers to effect dyeing.
このような染色方法によつて本願発明のモノア
ゾ化合物は、特に、塩素堅牢度、耐光堅牢度、汗
日光堅牢度にすぐれた黄色染色物を与える。特に
最近一般家庭における洗濯に塩素系漂白剤を使用
することが普及してきていることを考えると、塩
素堅牢度にすぐれる染色物を与える本発明モノア
ゾ化合物の価値は高い。また耐光、汗日光堅牢度
にすぐれることはスポーツウエア等外装着の染色
に好適である。 By such a dyeing method, the monoazo compound of the present invention provides a yellow dyed product particularly excellent in chlorine fastness, light fastness, and sweat/sunlight fastness. In particular, considering that the use of chlorine bleach in household laundry has recently become widespread, the value of the monoazo compound of the present invention, which provides dyed products with excellent chlorine fastness, is high. In addition, its excellent light fastness, sweat fastness and sunlight fastness make it suitable for dyeing external wear such as sportswear.
また本発明モノアゾ化合物は高い吸尽率を示す
ので、濃度の高い染色物を得ることができるのみ
ならず、染浴中に残存する染料分もわずかである
ことから、廃水処理の面でも有利である利点を有
する。 Furthermore, since the monoazo compound of the present invention exhibits a high exhaustion rate, it is possible not only to obtain dyed products with high density, but also to have a small amount of dye remaining in the dye bath, which is advantageous in terms of wastewater treatment. It has certain advantages.
また、本発明のモノアゾ化合物は均染性にすぐ
れ、染色適用温度の範囲も広く、かつ無機塩の添
加量および浴比による影響が小さいので、染色の
再現性がよい特徴も有している。 Furthermore, the monoazo compound of the present invention has excellent level dyeing properties, can be applied over a wide range of dyeing temperatures, and is less affected by the amount of inorganic salt added and the bath ratio, so it also has the characteristics of good dyeing reproducibility.
本発明に近似する染料として、たとえば特公昭
35−10628号公報には、たとえばフリーの酸の形
で下記
で示されるモノクロルトリアジン型黄色反応染料
が記載されている。しかし、これらの染料は染色
に高温を要し、また吸尽適性に欠けるため浸染用
としては濃度が出ない欠点を有している。また、
得られた染色物の酸安定性が低く、経時変化を受
けやすい欠点もある。 As a dye similar to the present invention, for example,
Publication No. 35-10628 describes, for example, the following in free acid form: A monochlorotriazine type yellow reactive dye represented by the following is described. However, these dyes require high temperatures for dyeing and lack exhaustion suitability, so they have the disadvantage that they do not produce a high density for dyeing. Also,
Another drawback is that the resulting dyed product has low acid stability and is susceptible to changes over time.
また、特公昭39−18184号公報には下記
で示される黄色反応染料が記載されている。しか
しこれらの染料の塩素堅牢度はISO法で１級と非
常に低く、実用的価値は小さいものである。 In addition, in Special Publication No. 39-18184, the following The yellow reactive dye shown is described. However, the chlorine fastness of these dyes is very low, being grade 1 according to the ISO method, and their practical value is small.
これに対して、本発明の黄色染料は、塩素堅牢
度がISO法で４級ないし４−５級と極めてすぐれ
ており、また耐光堅牢度が６−７級、汗日光堅牢
度が４級ないし４−５級といずれもすぐれてい
る。更に染色物の酸安定性（試験法は染布を１％
酢酸に30分浸漬後、パースピロメータを使用して
37±２℃の温度で125ｇ／cm2で６時間処理する）
も４−５級ないし５級と良好である。 On the other hand, the yellow dye of the present invention has an extremely excellent chlorine fastness of 4th grade or 4-5th grade according to the ISO method, a light fastness of 6th to 7th grade, and a sweat and sunlight fastness of 4th grade to 4th grade. All grades are excellent, 4th to 5th grade. Furthermore, the acid stability of dyed fabrics (test method is 1% dyed fabric)
After immersing in acetic acid for 30 minutes, using a perspirometer
(processed at 125g/ cm2 for 6 hours at a temperature of 37±2℃)
It is also good at grade 4-5 to grade 5.
次に本発明方法を実施例によつて説明する。文
中、部は重量部を表わす。 Next, the method of the present invention will be explained with reference to examples. In the text, parts represent parts by weight.
実施例 １
水100部中に２−アミノナフタレン−４，８−
ジスルホン酸6.1部と濃塩酸4.1部を含む溶液を０
〜10℃に冷却した後、亜硝酸ナトリウム1.4部を
水3.3部に溶かした液を注入し、同温度で30分間
撹拌する。過剰の亜硝酸を除去した後、水20部中
に濃塩酸2.3部と２−メトキシ−５−メチルアニ
リン2.7部を含む溶液を加え、０〜10℃で５時間
撹拌する。ついでこの溶液のPHを３〜５に調節し
てカツプリングを完了させた後、PHを８に上げ生
成物を溶解させ、塩化ナトリウム20部を加えて結
晶を再析出させる。これを吸引過し洗浄した
後、水100部に再溶解し、PHを６〜７に調節する。
この溶液に塩化シアヌル3.3部を加えて20〜25℃
で、20％炭酸ナトリウム水溶液を用いてPHを５〜
６に調整しながら、５時間撹拌する。Example 1 2-aminonaphthalene-4,8- in 100 parts of water
A solution containing 6.1 parts of disulfonic acid and 4.1 parts of concentrated hydrochloric acid was
After cooling to ~10°C, a solution of 1.4 parts of sodium nitrite dissolved in 3.3 parts of water is injected and stirred at the same temperature for 30 minutes. After removing excess nitrous acid, a solution containing 2.3 parts of concentrated hydrochloric acid and 2.7 parts of 2-methoxy-5-methylaniline in 20 parts of water is added and stirred at 0-10°C for 5 hours. After the coupling is completed by adjusting the pH of this solution to 3-5, the pH is raised to 8 to dissolve the product, and 20 parts of sodium chloride is added to re-precipitate the crystals. After suctioning and washing, it is redissolved in 100 parts of water and the pH is adjusted to 6-7.
Add 3.3 parts of cyanuric chloride to this solution and
Then, use 20% sodium carbonate aqueous solution to adjust the pH to 5~5.
Stir for 5 hours while adjusting the temperature to 6.
ついで１−アミノベンゼン−３−β−ヒドロキ
シエチルスルホン硫酸エステル5.6部を加えた後、
20％炭酸ナトリウム水溶液を用いてPHを５〜６に
調整しながら40℃に昇温し、同温度で５時間撹拌
する。この液に塩化ナトリウム20部を加えて結晶
を析出させ、吸引過し、洗浄した後、60℃で乾
燥してモノアゾ化合物(1)を得た。 Then, after adding 5.6 parts of 1-aminobenzene-3-β-hydroxyethylsulfone sulfate,
The temperature is raised to 40°C while adjusting the pH to 5 to 6 using a 20% aqueous sodium carbonate solution, and the mixture is stirred at the same temperature for 5 hours. 20 parts of sodium chloride was added to this solution to precipitate crystals, which were filtered under suction, washed, and dried at 60°C to obtain monoazo compound (1).
同様にして下記のモノアゾ化合物(2)、(3)を得
た。 In the same manner, the following monoazo compounds (2) and (3) were obtained.
実施例 ２
実施例１における２−メトキシ−５−メチルア
ニリン2.7部の代りに２−エトキシ−５−メチル
アニリン3.0部を用い実施例１と同様の方法で下
記のモノアゾ化合物(4)を得た。 Example 2 The following monoazo compound (4) was obtained in the same manner as in Example 1 using 3.0 parts of 2-ethoxy-5-methylaniline instead of 2.7 parts of 2-methoxy-5-methylaniline in Example 1. .
同様にして下記のモノアゾ化合物(5)、(6)を得
た。 In the same manner, the following monoazo compounds (5) and (6) were obtained.
参考例 １
実施例１で得られた式(1)のモノアゾ化合物0.3
部を200部の水に溶解し、芒硝20部を加え、木綿
10部を加えて50℃に昇温し、20分経過後炭酸ソー
ダ４部を加える。その温度で１時間染色する。染
色終了後、水洗、ソーピングを行なつて諸堅牢
度、特に塩素堅牢度のすぐれた高濃度の黄色染色
物が得られた。また染色の再現性もすぐれてい
た。（塩素堅牢度４−５級（ISO法）、汗日光堅牢
度４−５級、吸尽率99％、固着率93％）同様にし
て式(2)、(3)で示されるモノアゾ化合物を用いて染
色したところ同様の黄色染色物が得られた。 Reference Example 1 Monoazo compound of formula (1) obtained in Example 1 0.3
Dissolve 200 parts of water in 200 parts of water, add 20 parts of mirabilite, and mix with cotton.
Add 10 parts, raise the temperature to 50°C, and add 4 parts of soda carbonate after 20 minutes. Dye for 1 hour at that temperature. After dyeing, washing with water and soaping yielded a highly concentrated yellow dyed product with excellent fastness, especially fastness to chlorine. The reproducibility of staining was also excellent. (Chlorine fastness grade 4-5 (ISO method), sweat fastness to sunlight grade 4-5, exhaustion rate 99%, fixation rate 93%) In the same manner, monoazo compounds represented by formulas (2) and (3) were prepared. A similar yellow dyed product was obtained.
また、式(1)で示されるモノアゾ化合物のスルフ
アートエチルスルホン基がビニルスルホン基であ
るモノアゾ化合物を用い上記と同様の方法で染色
したところ同様の染色物が得られた。 Furthermore, when a monoazo compound represented by formula (1) in which the sulfate ethyl sulfone group is a vinyl sulfone group was dyed in the same manner as above, a similar dyed product was obtained.
参考例 ２
実施例２で得られた式(4)のモノアゾ化合物0.3
部を200部の水に溶解し、芒硝20部を加え、木綿
10部を加えて60℃に昇温し、20分経過後第三リン
酸ソーダ３部を加える。その温度で１時間染色す
る。染色終了後、水洗ソーピングを行なつて、実
施例１の式(1)の染料と同等の染色性能を有する塩
素堅牢度のすぐれた黄色の染色物が得られた。Reference Example 2 Monoazo compound of formula (4) obtained in Example 2 0.3
Dissolve 200 parts of water in 200 parts of water, add 20 parts of mirabilite, and mix with cotton.
Add 10 parts and raise the temperature to 60°C, and after 20 minutes add 3 parts of tribasic sodium phosphate. Dye for 1 hour at that temperature. After the dyeing was completed, washing and soaping were performed to obtain a yellow dyed product with excellent chlorine fastness and dyeing performance equivalent to that of the dye of formula (1) of Example 1.
同様にして式(5)、(6)で示されるモノアゾ化合物
を用いて染色したところ同様の重色染色物が得ら
れた。 When dyeing was carried out in the same manner using monoazo compounds represented by formulas (5) and (6), similar heavy-colored dyed products were obtained.
また、式(4)で示されるモノアゾ化合物のスルフ
アートエチルスルホン基がビニルスルホン基であ
るモノアゾ化合物を用い上記と同様の方法で染色
したところ同様の染色物が得られた。 Furthermore, when a monoazo compound represented by formula (4) in which the sulfate ethyl sulfone group is a vinyl sulfone group was dyed in the same manner as above, a similar dyed product was obtained.
Claims (1)
X2はそれぞれ水素、メチル基またはメトキシ基
を表わす。） で示されるモノアゾ化合物。 ２ ２−アミノナフタレン−４，８−ジスルホン
酸をジアゾ化し、一般式（） （式中、Ｒはメトキシ基またはエトキシ基を表わ
す。） で示されるトルイジン化合物とカツプリングさせ
て一般式（） （式中、Ｒは前記の意味を有する。） で示されるアミノモノアゾ化合物を得、これと塩
化シアヌルおよび一般式（）または（） （式中、X1、X2はそれぞれ水素、メチル基また
はメトキシ基を表わす。） で示されるアニリン化合物を任意の順序で縮合さ
せ、一般式（）で示されるアニリン化合物を用
いた場合は、次いで硫酸エステル化することを特
徴とする遊離酸の形で一般式（） （式中、Ｒ、X1、X2は前記の意味を有する。） で示されるモノアゾ化合物の製造方法。[Claims] 1 The following general formula in the form of a free acid: (In the formula, R is a methoxy group or an ethoxy group ,
X 2 each represents hydrogen, a methyl group or a methoxy group. ) A monoazo compound represented by 2 2-Aminonaphthalene-4,8-disulfonic acid is diazotized to give the general formula () (In the formula, R represents a methoxy group or an ethoxy group.) When coupled with a toluidine compound represented by the general formula () (In the formula, R has the above-mentioned meaning.) An aminomonoazo compound represented by the above formula is obtained, and this, cyanuric chloride and the general formula () or () (In the formula, X 1 and X 2 each represent hydrogen, a methyl group, or a methoxy group.) When the aniline compounds represented by the formula () are condensed in any order and the aniline compound represented by the general formula () is used, General formula () in the form of the free acid, characterized by subsequent sulfuric acid esterification (In the formula, R, X 1 and X 2 have the above-mentioned meanings.) A method for producing a monoazo compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59034022A JPS59161464A (en) | 1984-02-23 | 1984-02-23 | Monoazo compound and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59034022A JPS59161464A (en) | 1984-02-23 | 1984-02-23 | Monoazo compound and its preparation |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54069127A Division JPS5818471B2 (en) | 1979-06-01 | 1979-06-01 | Dyeing method for cellulose fibers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59161464A JPS59161464A (en) | 1984-09-12 |
| JPS6353230B2 true JPS6353230B2 (en) | 1988-10-21 |
Family
ID=12402747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59034022A Granted JPS59161464A (en) | 1984-02-23 | 1984-02-23 | Monoazo compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59161464A (en) |
-
1984
- 1984-02-23 JP JP59034022A patent/JPS59161464A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59161464A (en) | 1984-09-12 |
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