JPH0751674B2 - Bisazo compound and fiber dyeing method using the same - Google Patents
Bisazo compound and fiber dyeing method using the sameInfo
- Publication number
- JPH0751674B2 JPH0751674B2 JP57026504A JP2650482A JPH0751674B2 JP H0751674 B2 JPH0751674 B2 JP H0751674B2 JP 57026504 A JP57026504 A JP 57026504A JP 2650482 A JP2650482 A JP 2650482A JP H0751674 B2 JPH0751674 B2 JP H0751674B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- bisazo compound
- acid
- dyeing
- same
- 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
- -1 Bisazo compound Chemical class 0.000 title claims description 20
- 238000004043 dyeing Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 239000000835 fiber Substances 0.000 title description 8
- 239000002253 acid Substances 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 5
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003457 sulfones Chemical class 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 238000007796 conventional method Methods 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
- 125000004185 ester group Chemical group 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- IALORYHODRVWKZ-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylethyl sulfate;hydron Chemical compound NC1=CC=C(S(=O)(=O)CCOS(O)(=O)=O)C=C1 IALORYHODRVWKZ-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 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
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】 本発明は新規なビスアゾ化合物及びそれを用いるセルロ
ース系繊維の染色方法に関する。より詳しくは、本発明
は新規な繊維反応性ビスアゾ化合物及びそれを用いるセ
ルロース系繊維をネービー色に染色する方法に関する。The present invention relates to a novel bisazo compound and a method for dyeing cellulosic fibers using the same. More specifically, the present invention relates to a novel fiber-reactive bisazo compound and a method for dyeing cellulosic fibers using the same in a navy color.
セルロース系繊維を青色ないし黒色に染色する反応染料
としてC.I.Reactive Black5は公知であるが、一分子中
にビニルスルホン型の繊維反応性基を二個有するにもか
かわらずセルローズ系繊維に対して染着率が不充分であ
る問題を有している。CI Reactive Black5 is known as a reactive dye that dyes cellulosic fibers blue or black, but despite having two vinyl sulfone type fiber-reactive groups in one molecule, the dyeing rate for cellulose fibers Has a problem that is insufficient.
この問題を解決する目的で、特公昭43−15299号公報の
実施例13及び14は下式で示される染料（Ａ）及び（Ｂ）
が記載されている。In order to solve this problem, Examples 13 and 14 of JP-B-43-15299 disclose dyes (A) and (B) represented by the following formula.
Is listed.
更に特公昭45−4337号公報の実施例17には下式で示され
る染料（Ｃ）が記載されている。 Further, in Example 17 of JP-B-45-4337, a dye (C) represented by the following formula is described.
しかし、C.I.Reactive Black5に比して、染着率は染料
（Ａ）がその約60％、染料（Ｂ）が約50％及び染料
（Ｃ）が約60％にすぎず、しかもビルドアップ性の点に
おいても劣っており、前記問題点の解決には至っていな
い。 However, compared to CIReactive Black5, the dyeing rate is only about 60% for dye (A), about 50% for dye (B) and about 60% for dye (C), and the build-up point However, the above problems have not been solved yet.
本発明者らは斯かる問題点を解決するべく鋭意検討を行
った結果、構造中に特定個数のスルホン酸が特定の位置
に存在する特定のビスアゾ化合物がこれらの問題点を解
決し、すぐれた染着率及びビルドアップ性を有するネー
ビー色の濃度の高い染色物を与えることを見い出し、本
発明を完成するに至った。The present inventors have conducted extensive studies to solve such problems, and as a result, a specific bisazo compound having a specific number of sulfonic acids at specific positions in the structure solves these problems and is excellent. It has been found that a dyed product having a high density of navy having a dyeing rate and build-up property can be provided, and the present invention has been completed.
すなわち本発明は、遊離酸の形で下式一般式（Ｉ） 〔式中、R1,R2はそれぞれ独立に水素原子、メチル基ま
たはメトキシ基を示し、Ｑは基−SO2CH＝CH2または−SO
2CH2CH2Rを示す。ここにＲはアルカリで脱離する基であ
る。〕 で示されるビスアゾ化合物を提供する。That is, the present invention relates to the following general formula (I) in the form of free acid. [In the formula, R 1 and R 2 each independently represent a hydrogen atom, a methyl group or a methoxy group, and Q is a group —SO 2 CH═CH 2 or —SO
Indicates 2 CH 2 CH 2 R. Here, R is a group capable of leaving with an alkali. ] The bisazo compound shown by these is provided.
本発明はまた前記一般式（Ｉ）で示されるビスアゾ化合
物を用いることを特徴とするセルロース系繊維の染色方
法を提供する。The present invention also provides a method for dyeing cellulosic fibers, which comprises using the bisazo compound represented by the general formula (I).
前記一般式（Ｉ）におけるＱが−SO2CH2CH2Rであると
き、アルカリで除去し得る基Ｒは、例えばハロゲン原子
例えば塩素及び臭素原子、有機カルボン酸及びスルホン
酸のエステル基例えばアセチルオキシ残基のような低級
アルカノイルオキシ残基、ベンゾイルオキシ残基又はベ
ンゼンスルホニルオキシ基あるいは遊離酸の形で式−OP
O3H2若しくは−OSO3Hで表わされる燐酸又は硫酸の酸性
エステル基などである。When Q in the general formula (I) is —SO 2 CH 2 CH 2 R, an alkali-removable group R is, for example, a halogen atom such as chlorine and bromine atom, an ester group of organic carboxylic acid and sulfonic acid such as acetyl. A lower alkanoyloxy residue such as an oxy residue, a benzoyloxy residue or a benzenesulfonyloxy group or a free acid in the form of formula-OP
Examples thereof include an acid ester group of phosphoric acid or sulfuric acid represented by O 3 H 2 or —OSO 3 H.
本発明のビスアゾ化合物は遊離酸の形でもその塩の形で
も存在することができるが、塩、特にアルカリ金属及び
アルカリ土類金属、特にナトリウム、カリウム及びカル
シウム塩の形で在るのが好ましい。更に好ましい形はア
ルカリ金属塩である。The bisazo compounds according to the invention can be present in the free acid form or in the form of their salts, but are preferably in the form of salts, especially alkali metal and alkaline earth metals, especially sodium, potassium and calcium salts. A more preferred form is an alkali metal salt.
本発明の前記一般式（Ｉ）で示されるビスアゾ化合物
は、繊維反応性染料としての各種特性、例えば染着率、
アルカリ安定性、ビルドアップ性、ウオッシュオフ性な
どに優れ、かつ諸堅牢度も優れたネービー色の染色物を
与える有用な化合物である。The bisazo compound represented by the general formula (I) of the present invention has various properties as a fiber-reactive dye, for example, a dyeing rate,
It is a useful compound which gives a navy dyeing product which is excellent in alkali stability, build-up property, wash-off property and has various fastnesses.
一般式（Ｉ）で示される新規なビスアゾ化合物は次の様
にして製造できる。すなわち、２−ナフチルアミン−１
−スルホン酸を公知の方法によりジアゾ化し、１−アミ
ノ−８−ヒドロキシナフタレン−3,6−ジスルホン酸あ
るいはその塩の等モルを酸性媒体中、場合によっては反
応促進剤を添加のもとに、−５〜30℃においてカップリ
ングさせ、次に一般式（II） 〔式中、R1,R2及びＱは前記の意味を有する。〕 で示される芳香族アミンの等モルを公知の方法によりジ
アゾ化したものを加え、弱酸性〜弱アルカリ性下、−５
〜40℃においてカップリングさせることにより製造でき
る。The novel bisazo compound represented by the general formula (I) can be produced as follows. That is, 2-naphthylamine-1
-The sulfonic acid is diazotized by a known method, and an equimolar amount of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid or a salt thereof is added in an acidic medium, optionally with a reaction accelerator, Coupling at -5 to 30 ° C, then the general formula (II) [In the formula, R 1 , R 2 and Q have the above-mentioned meanings. ] A compound obtained by diazotizing an equimolar amount of the aromatic amine represented by
It can be produced by coupling at -40 ° C.
上記の出発化合物は、反応条件次第で酸および／または
塩、殊にアルカリ金属塩の形で存在するかまたはこの形
で使用される。Depending on the reaction conditions, the abovementioned starting compounds are present or used in the form of acids and / or salts, in particular alkali metal salts.
本発明により製造したビスアゾ化合物の分離は、一般に
公知の方法により、電解質例えば塩化ナトリウムまたは
塩化カリウムによる塩析あるいは反応溶液の蒸発、例え
ば噴霧乾燥により場合によっては安定剤等の助剤を添加
し、行うことができる。Separation of the bisazo compound produced according to the present invention is carried out by a generally known method, salting out with an electrolyte such as sodium chloride or potassium chloride or evaporation of the reaction solution, for example by spray drying and optionally adding an auxiliary agent such as a stabilizer, It can be carried out.
一般式（II）で示される芳香族アミンとして例えば次が
挙げられる。Examples of the aromatic amine represented by the general formula (II) include the following.
１−アミノゼンゼン−２−,3−または４−β−スルファ
ートエチルスルホン、 １−アミノ−２−または４−メトキシベンゼン−５−β
−スルファートエチルスルホン、 １−アミノ−２−メトキシ−５−メチルベンゼン−４−
β−スルファートエチルスルホン、 １−アミノ−2,5−ジメトキシベンゼン−４−β−スル
ファートエチルスルホン、 １−アミノ−2,4−ジメチルベンゼン−５−β−スルフ
ァートエチルスルホン、 １−アミノ−2,4−ジメトキシベンゼン−５−β−スル
ファートエチルスルホン および上記化合物において硫酸エステル基の代りに、燐
酸エステル基、アセチルオキシ基、プロピオニルオキシ
基、ｎ−またはiso−ブチリルオキシ基、ベンゾイルオ
キシ基またはベンゼンスルホニルオキシ基などが導入さ
れた化合物が挙げられる。1-aminozenen-2-, 3- or 4-β-sulfatoethyl sulfone, 1-amino-2- or 4-methoxybenzene-5-β
-Sulfate ethyl sulfone, 1-amino-2-methoxy-5-methylbenzene-4-
β-sulfatoethyl sulfone, 1-amino-2,5-dimethoxybenzene-4-β-sulfatoethyl sulfone, 1-amino-2,4-dimethylbenzene-5-β-sulfatoethyl sulfone, 1-amino -2,4-dimethoxybenzene-5-β-sulfatoethyl sulfone and the above compounds, instead of the sulfate ester group, a phosphate ester group, an acetyloxy group, a propionyloxy group, an n- or iso-butyryloxy group, a benzoyloxy group Alternatively, a compound into which a benzenesulfonyloxy group or the like is introduced can be used.
本発明のビスアゾ化合物はセルローズ繊維材料、例えば
天然または再生セルローズ、例えば木綿またはビスコー
スレーヨン材料を、水溶性反応染料を用いて実施される
通常の方法に従って染色できる。The bisazo compounds according to the invention can dye cellulose fiber materials, such as natural or regenerated cellulose materials, such as cotton or viscose rayon materials, according to the customary methods carried out with water-soluble reactive dyes.
例えばセルローズ系繊維の場合、本発明のビスアゾ化合
物を酸結合剤、例えば苛性ソーダ、炭酸ナトリウム、燐
酸塩または重曹を用いて染色を行う。染色方法は繊維の
性質及び物理的性状によって選択でき、例えば吸尽法、
捺染法またはコールドパッド−バッチ−アップ法を含む
連続染色法を採用できる。For example, in the case of cellulosic fibers, the bisazo compound of the present invention is dyed with an acid binder such as caustic soda, sodium carbonate, phosphate or baking soda. The dyeing method can be selected according to the properties and physical properties of the fiber, such as the exhaust method,
A continuous dyeing method including a printing method or a cold pad-batch-up method can be adopted.
本発明のビスアゾ化合物を繊維材料に染色する場合、特
公昭43−15299号公報及び特公昭45−4337号公報に記載
の染料に比して染着率において優れ、かつビルドアップ
性においても優れている。When dyeing a bisazo compound of the present invention on a fiber material, the dyeing rate is superior to the dyes described in JP-B-43-15299 and JP-B-45-4337, and the build-up property is also excellent. There is.
さらに、本発明化合物は１分子中に繊維反応性基を唯１
個有するにすぎないにもかかわらず、それを２個有する
C.I.Reactive Black5に比し、セルロース系繊維をより
濃色に染色できることはおどろくべきことである。Further, the compound of the present invention has only one fiber-reactive group in one molecule.
I have two, even though I only have one
Compared with CIReactive Black5, it is amazing that cellulosic fibers can be dyed in a darker color.
得られた染色物は良好な堅牢性、例えば良好な摩擦堅牢
性、良好な日光堅牢性及び良好な湿潤堅牢性、例えば洗
たく堅牢性、耐水性、酸及びアルカリ堅牢性、過酸化物
を含有する薬剤の処理に対する堅牢性等において優れて
いる。The dyeings obtained contain good fastnesses, such as good fastness to rubbing, good fastness to sunlight and good fastness to wet, such as washfastness, waterfastness, acid and alkali fastness, peroxides. It excels in robustness against chemical treatment.
次に本発明を実施例によって更に詳述に説明する。文
中、部は重量部を表わす。Next, the present invention will be described in more detail with reference to Examples. In the text, parts represent parts by weight.
実施例１ ２−ナフチルアミン−１−スルホン酸の11,15部を常法
によりジアゾ化後、過剰の亜硝酸をスルファミン酸で除
去し、ここへ１−アミノ−８−ヒドロキシナフタレン−
3,6−ジスルホン酸15.97部の中性溶液を０〜10℃、pH3
〜５において数時間かけて滴下し、一晩撹拌した。翌
朝、１−アミノベンゼン−４−β−スルファートエチル
スルホン14.05部を常法によりジアゾ化後、過剰の亜硝
酸をスルファミン酸で除去した溶液を加え、０〜10℃、
pH6〜8.5にてジアゾ化合物がもはや検出されなくなるま
で撹拌した。得られた染料液をpH4.5〜5.5とし、塩化カ
リウムで塩析精製することにより遊離酸の形で下式
（１）で示されるビスアゾ化合物を得た。Example 1 After diazotization of 11,15 parts of 2-naphthylamine-1-sulfonic acid by a conventional method, excess nitrous acid was removed with sulfamic acid, and 1-amino-8-hydroxynaphthalene was added thereto.
A neutral solution of 15.97 parts of 3,6-disulfonic acid was added at 0 to 10 ° C, pH 3
~ 5, added dropwise over several hours and stirred overnight. The next morning, 14.05 parts of 1-aminobenzene-4-β-sulfatoethyl sulfone was diazotized by a conventional method, a solution in which excess nitrous acid was removed with sulfamic acid was added, and the mixture was added at 0 to 10 ° C.
Stir until the diazo compound is no longer detected at pH 6-8.5. The resulting dye solution was adjusted to pH 4.5 to 5.5 and salted out with potassium chloride to obtain a bisazo compound represented by the following formula (1) in the form of a free acid.
〔λmax615nm（水溶媒）〕 上記染料0.6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℃に昇温した。ついで30分経過後、
炭酸ソーダ４部を加え同温度で１時間染色した。染色終
了後水洗、ソーピングを行って諸堅牢度の優れた、濃厚
なビルドアップ性の高いネービー色の染色物を得た。 [Λmax 615 nm (water solvent)] 0.6 parts of the above dye is dissolved in 200 parts of water, and 20 parts of Glauber's salt is added,
10 parts of cotton was added and the temperature was raised to 50 ° C. After 30 minutes,
4 parts of sodium carbonate was added and dyeing was carried out at the same temperature for 1 hour. After the completion of dyeing, the product was washed with water and soaped to obtain a navy-colored dyeing product having excellent fastness and a high build-up property.
実施例２〜９ 実施例１と同様の方法により下表に記載の原料化合物を
用い、夫々相当するビスアゾ化合物を得た。得られたビ
スアゾ化合物を用い実施例１と同様の方法で木綿を染色
し、式（１）で示される化合物と同様にすぐれた性能を
有するネービー色の染色物を得た。Examples 2 to 9 Using the raw material compounds described in the following table by the same method as in Example 1, the corresponding bisazo compounds were obtained. Using the obtained bisazo compound, cotton was dyed in the same manner as in Example 1 to obtain a navy dyed product having the same excellent performance as the compound represented by the formula (1).
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特公 昭45−4337（ＪＰ，Ｂ１) 特公 昭43−15299（ＪＰ，Ｂ１) 西独公開1644198（ＤＥ，Ａ１) ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References Japanese Patent Publication No. 45-4337 (JP, B1) Japanese Publication No. 43-15299 (JP, B1) Published in West Germany 1644198 (DE, A1)
Claims (2)
たはメトキシ基を示し、Ｑは基−SO2CH＝CH2または−SO
2CH2CH2Rを示す。ここにＲはアルカリで脱離する基であ
る。〕 で示されるビスアゾ化合物。1. The following general formula (I) in the form of a free acid. [In the formula, R 1 and R 2 each independently represent a hydrogen atom, a methyl group or a methoxy group, and Q is a group —SO 2 CH═CH 2 or —SO
Indicates 2 CH 2 CH 2 R. Here, R is a group capable of leaving with an alkali. ] The bisazo compound shown by these.
たはメトキシ基を示し、Ｑは基−SO2CH＝CH2または−SO
2CH2CH2Rを示す。ここにＲはアルカリで脱離する基であ
る。〕 で示されるビスアゾ化合物を用いることを特徴とするセ
ルロース系繊維の染色方法。2. The following general formula (I) in the form of a free acid. [In the formula, R 1 and R 2 each independently represent a hydrogen atom, a methyl group or a methoxy group, and Q is a group —SO 2 CH═CH 2 or —SO
Indicates 2 CH 2 CH 2 R. Here, R is a group capable of leaving with an alkali. ] The dyeing method of the cellulose fiber characterized by using the bisazo compound shown by these.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57026504A JPH0751674B2 (en) | 1982-02-19 | 1982-02-19 | Bisazo compound and fiber dyeing method using the same |
| US06/384,889 US4530996A (en) | 1981-06-15 | 1982-06-04 | Bisazo blue-black dye having vinylsulfone type fiber-reactive group |
| EP82105046A EP0068204B1 (en) | 1981-06-15 | 1982-06-08 | Reactive mono-functional bisazo blue-black dye |
| DE8282105046T DE3263244D1 (en) | 1981-06-15 | 1982-06-08 | Reactive mono-functional bisazo blue-black dye |
| KR8202658A KR890002642B1 (en) | 1981-06-15 | 1982-06-15 | Process for the preparation of reactive monofunctional bis azo blue-black dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57026504A JPH0751674B2 (en) | 1982-02-19 | 1982-02-19 | Bisazo compound and fiber dyeing method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58142938A JPS58142938A (en) | 1983-08-25 |
| JPH0751674B2 true JPH0751674B2 (en) | 1995-06-05 |
Family
ID=12195310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57026504A Expired - Lifetime JPH0751674B2 (en) | 1981-06-15 | 1982-02-19 | Bisazo compound and fiber dyeing method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0751674B2 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1644198A1 (en) | 1967-03-07 | 1971-07-15 | Hoechst Ag | Process for the preparation of water-soluble disazo dyes |
-
1982
- 1982-02-19 JP JP57026504A patent/JPH0751674B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1644198A1 (en) | 1967-03-07 | 1971-07-15 | Hoechst Ag | Process for the preparation of water-soluble disazo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58142938A (en) | 1983-08-25 |
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