JPH0144743B2 - - Google Patents
Info
- Publication number
- JPH0144743B2 JPH0144743B2 JP3207480A JP3207480A JPH0144743B2 JP H0144743 B2 JPH0144743 B2 JP H0144743B2 JP 3207480 A JP3207480 A JP 3207480A JP 3207480 A JP3207480 A JP 3207480A JP H0144743 B2 JPH0144743 B2 JP H0144743B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- group
- parts
- general formula
- 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
Links
- 238000004043 dyeing Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229920003043 Cellulose fiber Polymers 0.000 claims description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 26
- -1 monochlorotriazinyl group Chemical group 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000010016 exhaust dyeing Methods 0.000 description 5
- 239000000985 reactive dye Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 235000017550 sodium carbonate Nutrition 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
- 239000004753 textile Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 235000011121 sodium hydroxide 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
- 229940001496 tribasic sodium phosphate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Description
本発明はセルローズ系繊維材料を青色に染色す
る方法に関する。
更に詳しくは、本発明は遊離酸の形で下記一般
式（）
（式中、CuPcは銅フタロシアニン核、Ｗはスル
ホン酸基を１個有する１，３−または１，４−フ
エニレン基を表わす。
Y1、Y2はそれぞれ水素原子、メチル基、メト
キシ基またはスルホン酸基を表わす。
ｌ、ｍは、０から３までの正数、ｎは１から３
までの正数を示し、ｌ＋ｍ＋ｎは４より大きくな
いものとする。）
で示される染料を用いることを特徴とするセルロ
ーズ系繊維の染色方法である。
β−スルフアートエチルスルホニル基を有する
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ニル基を
有するフタロシアニン染料で吸尽染色性、特にビ
ルドアツプ性、低温固着性にすぐれ、かつ諸堅牢
性が良好なものは少なく、吸尽染色においてしば
しば問題となつていた。そのため吸尽染色におい
てビルドアツプ性、低温固着性にすぐれ、かつ諸
堅牢度が良好なフタロシアニン系青色反応染料の
出現が強く要望されている。
β−スルフアートエチルスルホニル基と異なる
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フタロシアニン系青色
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ているにすぎず、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、本発明者らは吸尽適性特
にビルドアツプ性、低温固着性にすぐれ、かつ諸
堅牢性が良好な青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、前記一般式
（）で示される染料、すなわち、反応基として
β−スルフアートエチルスルホニル基と、モノク
ロルトリアジニル基を有するフタロシアニン染料
が、すぐれた吸尽適性と良好な諸堅牢度を合わせ
持つ青色の染色物を与えることを見い出した。ま
た、本発明の染料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染料の欠点を解消できる
ことを見いだした。
本発明においてセルローズ系繊維としては、た
とえば木綿、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をあげる
ことができる。
本発明の染色は、吸尽法の場合、炭酸ソーダ第
三リン酸ソーダ、カ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
度で行なわれる。また捺染法による染色もでき
る。
本発明の染料は、たとえば次の様にして製造す
ることができる。
銅フタロシアニンをクロルスルホニル化し、つ
いでアミン化合物と縮合させて得られる一般式
（）
（式中、Ｗ、ｌ、ｍ及びｎは前記の意味を表わ
す。）
で示されるフタロシアニン化合物に塩化シアヌル
を一次的に縮合させてジクロルトリアジニル化合
物を得る。ついで、一般式（）
（式中、Y1、Y2は前記の意味を有する。）
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（）で示される染料を得ることができ
る。
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（）のフタロシアニン化合
物を縮合させることによつても、一般式（）の
染料を得ることができる。
あるいは一般式（）
（式中、Ｗ、Y1、Y2は前記の意味を表わす。）で
示される化合物を一般式（Ｖ）
（式中、ｊ、ｋはそれぞれ０から４までの正数を
表わし、ｊ＋ｋは４より大きくないものとする。）
で示される化合物にアンモニア水とともに縮合さ
せても一般式（）の染料を得ることができる。
あるいは一般式（）
（式中、Y1、Y2は前記の意味を有する。）
で示されるβ−ヒドロキシエチルスルホニル基を
有するアニリン化合物を前記一般式（）のアニ
リン化合物の代わりに用い、それぞれ同様の反応
を行なつた後、硫酸、スルフアミン酸などのエス
テル化剤を用いて通常の方法でエステル化するこ
とにより一般式（）の染料としても良い。
前記一般式（）の化合物としては、たとえば
次のものをあげることができる。
１−アミノベンゼン−２，３又は４−β−スル
フアートエチルスルホン、１−アミノ−２−メト
キシベンゼン−５−β−スルフアートエチルスル
ホン、１−アミノ−２−メトキシベンゼン−５−
β−スルフアートエチルスルホン、１−アミノ−
４−メトキシベンゼン−３−β−スルフアートエ
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−スルフアートエチルス
ルホン、１−アミノ−２−スルホベンゼン−４−
β−スルフアートエチルスルホン、１−アミノ−
２−スルホベンゼン−５−β−スルフアートエチ
ルスルホン、１−アミノ−２−メチルベンゼン−
５−β−スルフアートエチルスルホン、１−アミ
ノ−４−メチル−３−β−スルフアートエチルス
ルホン。
このようにして得られた本発明染料は、吸尽染
色適性、特にビルドアツプ性、低温固着性にすぐ
れ、かつ諸堅牢度が良好である。さらに本発明染
料は高い吸尽率、固着率を示すので、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。
本発明に近似する染料として、たとえば特公昭
39−18184号公報には、下記
で示される青色反応染料が記載されているが、本
発明染料は上記染料に比較して溶解性及びウオツ
シユオフ性にすぐれており、また吸尽適性が良好
であり実用的価値が大きい。
次に本発明方法を実施例によつて説明する。
文中、部は重量部を示す。
実施例 １
式(1)
で示される染料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℃に昇温する。
ついで30分経過後、炭酸ソーダ４部を加え同温度
で１時間染色する。
染色終了後、水洗、ソーピングを行なつてビル
ドアツプ性及び諸堅牢度のすぐれた青色の染色物
が得られた。
同様にして塩化シアヌルと下記一般式（）お
よび一般式（）を成分として得られる染料(2)、
(3)を用いて実施例１と同様に染色したところ、い
ずれも諸堅牢度が良好でかつビルドアツプ性にす
ぐれた青色の染色物が得られた。
The present invention relates to a method for dyeing cellulosic fiber materials blue. More specifically, the present invention provides the following general formula () in the form of a free acid: (In the formula, CuPc represents a copper phthalocyanine nucleus, and W represents a 1,3- or 1,4-phenylene group having one sulfonic acid group. Y 1 and Y 2 are a hydrogen atom, a methyl group, a methoxy group, or a sulfone group, respectively. Represents an acid group. l, m are positive numbers from 0 to 3, n is 1 to 3.
It is assumed that l+m+n is not greater than 4. ) This is a method for dyeing cellulose fibers, which is characterized by using the dye shown in the following. It is known that dyes having a β-sulfatoethylsulfonyl group can be applied as so-called vinylsulfone type reactive dyes for dyeing textile materials.
However, there are few phthalocyanine dyes having a β-sulfatoethylsulfonyl group that have excellent exhaust dyeing properties, especially build-up properties, low-temperature fixing properties, and good fastness properties, which often causes problems in exhaust dyeing. Ta. Therefore, there is a strong demand for a phthalocyanine-based blue reactive dye that has excellent build-up properties, low-temperature fixing properties, and good fastness properties in exhaust dyeing. Phthalocyanine blue dyes with a monochlorotriazinyl group as another typical reactive group different from the β-sulfatoethylsulfonyl group are also known, but these reactive dyes generally require high dyeing temperatures. In addition, it is only used for textile printing because it is not suitable for exhaust dyeing.Furthermore, it has the disadvantage that the acid stability of the dyed product obtained is low, so it is never practical. I couldn't say it was enough. For this reason, the present inventors have conducted intensive studies in search of a blue vinyl sulfone type reactive dye that is excellent in exhaustion suitability, especially build-up properties, and low-temperature fixing properties, and has good various fastness properties. The dye represented by the general formula (), that is, a phthalocyanine dye having a β-sulfatoethylsulfonyl group and a monochlorotriazinyl group as reactive groups, has both excellent exhaust suitability and good fastness properties. It has been found that it gives a blue dye. It has also been found that the dye of the present invention can overcome the drawbacks of reactive dyes having a monochlorotriazinyl group as described above. In the present invention, the cellulose fibers include natural or regenerated cellulose fibers such as cotton, linen, viscose human silk, and viscose cotton. In the case of the exhaust method, the dyeing of the present invention 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. The dye of the present invention can be produced, for example, as follows. General formula () obtained by chlorosulfonylating copper phthalocyanine and then condensing it with an amine compound (In the formula, W, l, m, and n represent the above-mentioned meanings.) A dichlorotriazinyl compound is obtained by primary condensation of cyanuric chloride with a phthalocyanine compound represented by the following formula. Then, the general formula () (In the formula, Y 1 and Y 2 have the above-mentioned meanings.) The dye represented by the general formula () can be obtained by secondarily condensing the aniline compound represented by the following. Alternatively, the dye of the general formula () can also be obtained by first condensing an aniline compound represented by the general formula () with cyanuric chloride, and then secondarily condensing the phthalocyanine compound of the general formula (). be able to. Or general expression () (In the formula, W, Y 1 and Y 2 represent the above meanings.) A compound represented by the general formula (V) (In the formula, j and k each represent a positive number from 0 to 4, and j+k shall not be larger than 4.) The dye of general formula () can also be obtained by condensing the compound represented by with aqueous ammonia. be able to. Or general expression () (In the formula, Y 1 and Y 2 have the above-mentioned meanings.) Using an aniline compound having a β-hydroxyethylsulfonyl group represented by the above formula () in place of the aniline compound of the above general formula (), the same reaction was carried out. After aging, it may be esterified using an esterifying agent such as sulfuric acid or sulfamic acid in a conventional manner to obtain a dye of the general formula (). Examples of the compound of the general formula () include the following. 1-aminobenzene-2,3 or 4-β-sulfatoethylsulfone, 1-amino-2-methoxybenzene-5-β-sulfatoethylsulfone, 1-amino-2-methoxybenzene-5-
β-sulfatoethyl sulfone, 1-amino-
4-Methoxybenzene-3-β-sulfatoethylsulfone, 1-amino-2-methoxy-5-
Methylbenzene-4-β-sulfatoethylsulfone, 1-amino-2-sulfobenzene-4-
β-sulfatoethyl sulfone, 1-amino-
2-Sulfobenzene-5-β-sulfatoethylsulfone, 1-amino-2-methylbenzene-
5-β-sulfatoethylsulfone, 1-amino-4-methyl-3-β-sulfatoethylsulfone. The dye of the present invention thus obtained has excellent exhaust dyeing suitability, particularly build-up property and low-temperature fixing property, and has good various fastness properties. Furthermore, since the dye of the present invention exhibits a high exhaustion rate and fixation rate, it is possible not only to obtain dyed products with high density, but also to be advantageous in terms of wastewater treatment since only a small amount of dye remains in the dye bath. It has the advantage of being As a dye similar to the present invention, for example,
Publication No. 39-18184 states the following: The dye of the present invention has better solubility and wash-off property than the above-mentioned dyes, and has good exhaustion suitability, so it has great practical value. Next, the method of the present invention will be explained with reference to examples. In the text, parts indicate parts by weight. Example 1 Formula (1) Dissolve 0.3 parts of the dye shown in 200 parts of water and add mirabilite.
Add 20 parts, add 10 parts of cotton, and raise the temperature to 60℃.
After 30 minutes, 4 parts of soda carbonate is added and dyed at the same temperature for 1 hour. After dyeing, washing with water and soaping were performed to obtain a blue dyed product with excellent build-up properties and various fastnesses. Dye (2) obtained in the same manner using cyanuric chloride and the following general formula () and general formula () as components,
When dyeing was carried out in the same manner as in Example 1 using (3), blue dyed products with good fastness properties and excellent build-up properties were obtained.
【表】
参考例 １
〔実施例１の染料(1)の合成〕
上記フタロシアン化合物50部を水200部に溶解
し、ソーダ灰でPH６−７に調整する。ついで０−
５℃に冷却し、この液に塩化シアヌル9.5部を加
え０−５℃でPH６−７に調整しつつ４時間保温す
る。その後温度30−35℃に昇温し、１−アミノベ
ンゼン−３−β−スルフアートエチルスルホン
16.9部を加え、PH４−５で４時間保温する。つい
で塩化ナトリウム30部を加えて結晶を析出させ、
過し、洗浄した後、乾燥して染料(1)を得た。
実施例 ２
で示される染料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℃に昇温する。
20分経過後、炭酸ソーダ４部を加え、同温度で
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が良好でビルドアツプ性のす
ぐれた青色の染色物が得られた。
同様にして塩化シアヌルと下記一般式（）お
よび一般式（）を成分として得られる染料(5)、
(6)を用いて実施例２と同様に染色したところ、い
ずれも諸堅牢度が良好で、かつビルドアツプ性に
すぐれた青色の染色物が得られた。[Table] Reference example 1 [Synthesis of dye (1) of Example 1] Dissolve 50 parts of the above phthalocyan compound in 200 parts of water, and adjust the pH to 6-7 with soda ash. Then 0-
Cool to 5°C, add 9.5 parts of cyanuric chloride to this solution, and keep warm for 4 hours while adjusting the pH to 6-7 at 0-5°C. After that, the temperature was raised to 30-35℃, and 1-aminobenzene-3-β-sulfatoethyl sulfone
Add 16.9 parts and keep warm at PH4-5 for 4 hours. Then, 30 parts of sodium chloride was added to precipitate crystals.
After filtering, washing, and drying, dye (1) was obtained. Example 2 Dissolve 0.3 parts of the dye shown in 200 parts of water and add 20 parts of mirabilite.
1 part, add 10 parts of cotton, and raise the temperature to 50℃. After 20 minutes, add 4 parts of soda carbonate and dye at the same temperature for 1 hour. After dyeing, washing with water and soaping yielded a blue dyed product with good fastness and build-up properties. Dye (5) obtained in the same manner using cyanuric chloride and the following general formula () and general formula () as components,
When dyeing was carried out in the same manner as in Example 2 using (6), blue dyed products with good fastness properties and excellent build-up properties were obtained.
【表】
参考例 ２
〔実施例２の染料(4)の合成〕
水50部に１−アミノベンゼン−３−β−スルフ
アートエチルスルホン14.0部を加え、ソーダ灰で
PH４±0.5に調整後０−５℃に冷却する。この液
に塩化シアヌル9.5部を加え、０〜５℃でPH２〜
３に調整しつつ１時間保温する。ついで30−35℃
に昇温し、この液に下式
で示されるフタロシアニン化合物55部の水溶液
250部を加え、PH６±0.5に調整しつつ温度30〜35
℃で４時間保温する。
ついで塩化ナトリウム30部を加えて結晶を析出
させ、過し、洗浄した後、乾燥して染料(4)を得
た。[Table] Reference Example 2 [Synthesis of dye (4) of Example 2] Add 14.0 parts of 1-aminobenzene-3-β-sulfatoethyl sulfone to 50 parts of water, and mix with soda ash.
After adjusting the pH to 4±0.5, cool to 0-5℃. Add 9.5 parts of cyanuric chloride to this solution, and at 0 to 5°C, pH 2 to
Adjust the temperature to 3 and keep warm for 1 hour. Then 30-35℃
The temperature is raised to , and the following formula is applied to this liquid. An aqueous solution of 55 parts of a phthalocyanine compound represented by
Add 250 parts and adjust the pH to 6 ± 0.5 while raising the temperature to 30-35.
Incubate at ℃ for 4 hours. Then, 30 parts of sodium chloride was added to precipitate crystals, which were filtered, washed, and dried to obtain dye (4).
Claims (1)
ホン酸基を１個有する１，３−または１，４−フ
エニレン基を表わす。 Y1、Y2はそれぞれ水素原子、メチル基、メト
キシ基またはスルホン酸基を表わす。 ｌ、ｍは０から３までの正数、ｎは１から３ま
での正数を示し、ｌ＋ｍ＋ｎは４より大きくない
ものとする。） で示される染料を用いることを特徴とするセルロ
ーズ系繊維材料の染色方法。[Claims] 1 The following general formula in the form of a free acid: (In the formula, CuPc represents a copper phthalocyanine nucleus, and W represents a 1,3- or 1,4-phenylene group having one sulfonic acid group. Y 1 and Y 2 are a hydrogen atom, a methyl group, a methoxy group, or a sulfone group, respectively. Represents an acid group. l and m are positive numbers from 0 to 3, n is a positive number from 1 to 3, and l+m+n is not larger than 4.) A method for dyeing cellulose fiber materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3207480A JPS56128375A (en) | 1980-03-12 | 1980-03-12 | Dyeing of cellulosic fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3207480A JPS56128375A (en) | 1980-03-12 | 1980-03-12 | Dyeing of cellulosic fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56128375A JPS56128375A (en) | 1981-10-07 |
| JPH0144743B2 true JPH0144743B2 (en) | 1989-09-29 |
Family
ID=12348723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3207480A Granted JPS56128375A (en) | 1980-03-12 | 1980-03-12 | Dyeing of cellulosic fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56128375A (en) |
-
1980
- 1980-03-12 JP JP3207480A patent/JPS56128375A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56128375A (en) | 1981-10-07 |
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