JPS646316B2 - - Google Patents
Info
- Publication number
- JPS646316B2 JPS646316B2 JP7571981A JP7571981A JPS646316B2 JP S646316 B2 JPS646316 B2 JP S646316B2 JP 7571981 A JP7571981 A JP 7571981A JP 7571981 A JP7571981 A JP 7571981A JP S646316 B2 JPS646316 B2 JP S646316B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dyeing
- parts
- dye
- polyester
- 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 29
- 238000000034 method Methods 0.000 claims description 10
- -1 azo compound Chemical class 0.000 claims description 7
- 229920003043 Cellulose fiber Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 description 19
- 239000000975 dye Substances 0.000 description 17
- 239000000986 disperse dye Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000982 direct dye Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 239000000243 solution 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- VKURVCNKVWKGLX-UHFFFAOYSA-N 5-amino-2-(4-aminoanilino)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1S(O)(=O)=O VKURVCNKVWKGLX-UHFFFAOYSA-N 0.000 description 1
- GDBANHJMXDZUNE-UHFFFAOYSA-N 5-hydroxynaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC=CC2=C1 GDBANHJMXDZUNE-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- MPCYPRXRVWZKGF-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C=C4C=C(C=C(C4=C3O)N)S([O-])(=O)=O)S([O-])(=O)=O)=C(O)C2=C1N MPCYPRXRVWZKGF-UHFFFAOYSA-J 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明は遊離酸の形で式 （式中R1は−SO3Hを、R2はＨを表わす。 Ｘは The present invention is formulated in the free acid form. (In the formula, R 1 represents -SO 3 H, R 2 represents H.
【式】【formula】
【式】 又は【formula】 or
【式】 を表わし、R3はＨ又は[Formula], R 3 is H or
【式】を表わ
し、R4はＨ、−COCH3又は−CONH2を表わし、
R5は[Formula], R 4 represents H, -COCH 3 or -CONH 2 ,
R5 is
【式】を表わし、R6は Ｈ、CH3又は[Formula], R 6 is H, CH 3 or
【式】を表わし、R7はＨ又は[Formula], R 7 is H or
【式】を表わす。）
で表わされるアゾ化合物を用いてセルローズ繊維
をいつたん染色し、更に銅処理する事を特徴とす
るセルローズ繊維の染色法に関する。セルローズ
繊維を日光及び洗濯に堅牢な黒色に染色する多く
の直接染料が、特許や文献に見られ、又CI
Direct Black19、22、39等の染料が市場で使用
されている。しかしこれらの染料はいずれも、ポ
リエステル／セルローズ混紡品を分散染料と一緒
に１浴１段の浸染染法で高温染色する場合（最近
の人件費及び石油価格の高騰は染工場の加工コス
トを著しく増大させているため、染色時間の短縮
と省力、省エネルギーの見地からポリエステル側
の分散染料と、セルローズ側の直接染料を分散染
料の染色条件で同時染色を行う事が望まれてい
る。）には
著しく染着率が低下するとか
染浴で染料の凝集が起るとか
粘性があるため再現性の良い染色物が得られ
ない。
等の理由に依り、実用上、１浴１段染色には適さ
ず、やむなく省力、省エネルギーの見地から好ま
しくない、２溶、２段染色法、又は１浴２段染色
法（ポリエステル側を分散染料で染色した後に、
同一浴でセルローズ側を直接染料で染色する方
法）を、とらざるを得ないという欠点を有してい
る。それ故に、酸性浴高温染色適性（分散染料に
よるポリエステル繊維の高温酸性浴条件でセルロ
ーズに染色可能な性質）のある堅牢な黒色の直接
染料の出現が強く望まれていた。本発明の目的
は、その要望を満たし酸性浴高温染色適性があ
り、分散染料と一緒に１浴１段でポリエステル／
セルローズ混紡品を染色出来、堅牢な黒色のアゾ
化合物による染色法を提供しようとするものであ
る。
本発明に使用されるアゾ化合物は、次の様な方
法で製造することが出来る。
式
（式中R1、R2は前記のものを表わす。）
のアミンのテトラゾ化物を、２−アミノ−８−ヒ
ドロキシナフタレン−６−スルフオン酸２モルと
アルカリ性下で好ましくは10℃近辺でカツプリン
グさせ式
（式中、R1、R2は前記のものを意味する。）
のジアミノ、ジスアゾ染料を製造し、次いでこれ
をテトラゾ化し、Represents [formula]. ) This invention relates to a method for dyeing cellulose fibers, which is characterized in that cellulose fibers are dyed using an azo compound represented by the following formula, and then treated with copper. Many direct dyes for dyeing cellulose fibers to sunlight- and wash-fast black colors can be found in patents and literature, and in CI
Dyes such as Direct Black 19, 22, and 39 are used in the market. However, all of these dyes are difficult to use when dyeing polyester/cellulose blends together with disperse dyes at high temperatures using a one-bath, one-step dip dyeing method (recently rising labor costs and oil prices have significantly increased processing costs at dyeing factories). Therefore, from the viewpoint of shortening the dyeing time, saving labor, and saving energy, it is desirable to perform simultaneous dyeing with the disperse dye on the polyester side and the direct dye on the cellulose side under the dyeing conditions of the disperse dye.) Dyeing rate may drop significantly, Dye agglomeration may occur in the dye bath, and Dyeing with good reproducibility cannot be obtained due to viscosity. For these reasons, it is practically unsuitable for one-bath, one-stage dyeing, and unavoidably undesirable from the viewpoint of labor and energy saving. After dyeing with
It has the disadvantage that it requires a method in which the cellulose side is directly dyed with a dye in the same bath. Therefore, there has been a strong desire for a strong black direct dye that is suitable for acid bath high temperature dyeing (the ability to dye cellulose in polyester fibers using disperse dyes under high temperature acid bath conditions). The purpose of the present invention is to meet this demand, to be suitable for acid bath high temperature dyeing, and to dye polyester/polyester in one bath and one stage together with disperse dyes.
The purpose of the present invention is to provide a dyeing method using an azo compound that is capable of dyeing cellulose blended fabrics and provides a durable black color. The azo compound used in the present invention can be produced by the following method. formula (In the formula, R 1 and R 2 represent the above.) A tetrazotized product of the amine is coupled with 2 moles of 2-amino-8-hydroxynaphthalene-6-sulfonic acid under alkaline conditions, preferably at around 10°C. formula (In the formula, R 1 and R 2 mean the above-mentioned ones.) Produce a diamino, disazo dye, and then tetrazotize it,
【式】１モルと弱
酸性で好ましくは10℃以下でカツプリング後、
式
Ｘ−Ｈ (4)
（式中Ｘは前記のものを意味する）
のカツプリング成分１モルとアルカリ性下、好ま
しくは５℃以下でカツプリングさせる事に依つて
得られる。
式(4)のカツプリング成分は、例えば[Formula] After coupling with 1 mol of a coupling component of the formula It can be obtained by coupling as follows. The coupling component of equation (4) is, for example,
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】
などが挙げられる。
本発明の染色法によると天然又は人造のセルロ
ーズ繊維を直接染料で染色する普通の染色条件に
よる染色法、例えば、浸染、連続染色、又は色糊
を調整し、これを用いて捺染する方法、並びりポ
リエステル繊維を分散染料で染色する際の普通の
染色条件による染色法、例えば、高温染色、サー
モゾル染色、更に捺染する方法で湿潤及び日光に
堅牢な極めて馬力のある黒色に染色する事が出来
る。
すなわち、式(1)のアゾ化合物を単独或いは式(1)
のアゾ化合物と他の染料（例えば分散染料）の混
合物からなる染浴又は捺染用ペーストを調製し、
セルローズ、ポリエステル／セルローズの混紡又
は交織品などを所望の方法で染色又は捺染し、そ
の後染色物を銅処理すなわち好ましくは含銅ポリ
アミン系フイツクス剤の水溶液に上記染色物を入
れ例えば15〜80℃でフイツクス処理を行い、繊維
上で銅錯塩染料を形成させその後ソーピングする
事により染色を完了させる事が出来る。
特にポリエステル／セルローズ混紡品を分散染
料例えばKayalon Polyester Black EX−SF200
（日本化薬製）Kayalon Polyester Black BR−
SF（日本化薬製）Dianix Black BG−SF conc
Paste（三菱化成）Palanyl Black GEL liq
（BASF）などと一緒に１浴で使用して、分散染
料の染色条件でセルローズ側を均一に染色出来る
更に大きな特徴がある。
以下に実施例を挙げて、本発明を説明するが本
発明はこれら実施例に限定されるものではない。
尚実施例中、部は重量部を意味し、水溶性基を
有する原料及び目的物は、すべて遊離酸の形で示
す。
実施例 １
ポリエステル／綿、混紡品の高温一浴染色：
下記表中の式(5)の化合物0.3部、無水硫酸ナト
リウム８部、Kayalon Polyester Black EX−
SF200（日本化薬製分散染料）0.5部、酢酸ナトリ
ウム、３水塩0.92部、酢酸0.13部、水400部でPH
55の染浴を調製する。
この染浴を50℃とし、ポリエステル／綿（50/5
０）混紡品20部を入れ、30分で130℃に昇温させ、
この温度で45分間染色を続けた後、20分を要して
60℃まで降温させる。
その後染色物を取り出し、水洗した後これを、
サンフイツクス555C（三洋化成(株)製、含銅ポリア
ミン系のフイツクス剤）1.2部を水400部に溶解し
た水溶液に入れ、60℃で20分間フイツクス処理を
施し、ソーピング、水洗、乾燥する。この様にし
て得られた、ポリエステル／綿の混紡品は均一な
黒色に染色され、すぐれた耐光、洗濯堅牢度を有
する。
式(5)のアゾ化合物は以下のようにして製造す
る。４，4′−ジアミノジフエニルアミン−2′−ス
ルホン酸5.6部を水50部に懸濁し、ついでカセイ
ソーダ0.6部を加えて溶解させる。次にこの溶液
を５℃以下に冷却し、濃塩酸9.3部、亜硝酸ソー
ダ３部を用いて５〜10℃で２時間かけてテトラゾ
化する。このテトラゾ化液を、２−アミノ−８−
ヒドロキシナフタレン−６−スルホン酸9.1部、
ソーダ灰11部、水100部の混合液に入れ15〜20℃
で終夜攪拌する。
このようにして得られたジアミノジスアゾ染料
を濃塩酸26部、亜硝酸ソーダ3.3部で５〜20℃で
１時間かけてテトラゾ化する。ついでこテトラゾ
化液にメタアミノフエノール4.2部を60℃の水30
部に溶解したものを加えたのちソーダ灰10部を加
えアルカリ性とし、反応を終了させる。ついで塩
化ナトリウム35部を加え、塩析、過し生成物を
90℃で乾燥させる。
実施例 ２
ポリエステル／レーヨン混紡品の高温一浴染
色：
下記表中の(5)の化合物0.3部、Kayarus Cupro
Green Ｇ（日本化薬製直接染料）0.1部、無水硫
酸ナトリウム８部、Kayalon Polyster Black
EX−SF200（日本化薬製分散染料）0.5部、ウル
トラMTレベル（御幣島化学工業製）8.8部、水
400部でPH6.0の染浴を調製する。
その後、実施例１と同一条件で染色、水洗、フ
イツクス処理、ソーピング、水洗、乾燥する。
この様にして得られた、ポリエステル／レーヨ
ンの混紡品は均一な黒色に染色され、すぐれた耐
光、染濯堅牢度を有する。
実施例 ６〜13
下記表中式(6)〜（13）の化合物も、実施例１と
同様に製造し、実施例１、２と同様にポリエステ
ル／綿、ポリエステル／レーヨンの混紡品を高温
一浴で染色する事が出来、得られた染色物は、均
一な黒色に染色され、すぐれた耐光、染濯堅牢度
を有する。[Formula] etc. According to the dyeing method of the present invention, natural or artificial cellulose fibers are dyed directly with dyes using ordinary dyeing conditions, such as dip dyeing, continuous dyeing, or a method of adjusting colored paste and printing using the same; It is possible to dye polyester fibers in extremely strong black color, which is fast to moisture and sunlight, using the usual dyeing conditions when dyeing polyester fibers with disperse dyes, such as high temperature dyeing, thermosol dyeing, and printing. That is, the azo compound of formula (1) alone or
preparing a dyebath or printing paste consisting of a mixture of the azo compound and other dyes (e.g. disperse dyes);
Cellulose, polyester/cellulose blends or textiles are dyed or printed by a desired method, and then the dyed product is treated with copper, i.e., the dyed product is preferably placed in an aqueous solution of a copper-containing polyamine fixing agent at 15 to 80°C. Dyeing can be completed by performing a fixing process to form a copper complex dye on the fibers, followed by soaping. In particular, polyester/cellulose blends are treated with disperse dyes such as Kayalon Polyester Black EX-SF200.
(Nippon Kayaku) Kayalon Polyester Black BR−
SF (Nippon Kayaku) Dianix Black BG−SF conc
Paste (Mitsubishi Kasei) Palanyl Black GEL liq
Another great feature is that it can be used in one bath with dyes such as (BASF) to uniformly dye the cellulose side under disperse dye dyeing conditions. The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples. In the examples, parts mean parts by weight, and all raw materials and target products having water-soluble groups are shown in the form of free acids. Example 1 High-temperature one-bath dyeing of polyester/cotton blend: 0.3 parts of the compound of formula (5) in the table below, 8 parts of anhydrous sodium sulfate, Kayalon Polyester Black EX-
PH with 0.5 parts of SF200 (Nippon Kayaku disperse dye), sodium acetate, 0.92 parts of trihydrate, 0.13 parts of acetic acid, and 400 parts of water.
Prepare 55 dyebaths. This dye bath was heated to 50℃ and polyester/cotton (50/5
0) Add 20 parts of the blended product and raise the temperature to 130℃ for 30 minutes.
After continuing staining at this temperature for 45 minutes, it took 20 minutes to
Lower the temperature to 60℃. After that, take out the dyed material, wash it with water, and then
Add 1.2 parts of Sun Fixtures 555C (manufactured by Sanyo Kasei Co., Ltd., copper-containing polyamine type fixing agent) to 400 parts of water, apply fixing treatment at 60°C for 20 minutes, soap, wash with water, and dry. The polyester/cotton blend thus obtained is dyed uniformly black and has excellent light fastness and washing fastness. The azo compound of formula (5) is produced as follows. 5.6 parts of 4,4'-diaminodiphenylamine-2'-sulfonic acid are suspended in 50 parts of water, and then 0.6 part of caustic soda is added and dissolved. Next, this solution is cooled to 5 DEG C. or below, and tetrazotized using 9.3 parts of concentrated hydrochloric acid and 3 parts of sodium nitrite at 5 DEG to 10 DEG C. over 2 hours. This tetrazotized solution was converted into 2-amino-8-
9.1 parts of hydroxynaphthalene-6-sulfonic acid,
Add to a mixture of 11 parts of soda ash and 100 parts of water at 15-20℃.
Stir overnight. The diaminodisazo dye thus obtained is tetrazotized with 26 parts of concentrated hydrochloric acid and 3.3 parts of sodium nitrite at 5 DEG to 20 DEG C. over 1 hour. Next, add 4.2 parts of meta-aminophenol to the tetrazotized solution and add 30 parts of water at 60℃.
After adding 1 part of the dissolved material, 10 parts of soda ash is added to make it alkaline and the reaction is terminated. Next, add 35 parts of sodium chloride, salt out, and filter the product.
Dry at 90℃. Example 2 High-temperature one-bath dyeing of polyester/rayon blend: 0.3 parts of compound (5) in the table below, Kayarus Cupro
Green G (Nippon Kayaku direct dye) 0.1 part, anhydrous sodium sulfate 8 parts, Kayalon Polyster Black
EX-SF200 (Nippon Kayaku disperse dye) 0.5 parts, Ultra MT Level (Mitejima Chemical Industries) 8.8 parts, water
Prepare a dyebath of PH6.0 with 400 parts. Thereafter, dyeing, washing, fixing, soaping, washing, and drying were carried out under the same conditions as in Example 1. The polyester/rayon blend thus obtained is dyed uniformly black and has excellent light fastness and dye fastness. Examples 6 to 13 Compounds of formulas (6) to (13) in the table below were also produced in the same manner as in Example 1, and polyester/cotton and polyester/rayon blends were heated in a high-temperature bath in the same manner as in Examples 1 and 2. The resulting dyed product is uniformly black and has excellent light fastness and dye fastness.
【表】【table】
【表】【table】
Claims (1)
R5は【式】を表わし、R6は Ｈ、−CH3又は【式】を表わし、R7はＨ又 は【式】を表わす。） で表わされるアゾ化合物を用いてセルローズ繊維
をいつたん染色し、更に銅処理する事を特徴とす
るセルローズ繊維の染色法。[Claims] 1. In the form of free acid, the formula (In the formula, R 1 represents -SO 3 H, R 2 represents H. X represents [Formula] [Formula] or [Formula], R 3 represents H or [Formula], R 4 represents H , -COCH 3 or -CONH 2 ;
R 5 represents [Formula], R 6 represents H, -CH 3 or [Formula], and R 7 represents H or [Formula]. ) A method for dyeing cellulose fibers, which is characterized in that cellulose fibers are dyed with an azo compound represented by the following formula, and then further treated with copper.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7571981A JPS57192465A (en) | 1981-05-21 | 1981-05-21 | New azo compound and method of dyeing using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7571981A JPS57192465A (en) | 1981-05-21 | 1981-05-21 | New azo compound and method of dyeing using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57192465A JPS57192465A (en) | 1982-11-26 |
| JPS646316B2 true JPS646316B2 (en) | 1989-02-02 |
Family
ID=13584341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7571981A Granted JPS57192465A (en) | 1981-05-21 | 1981-05-21 | New azo compound and method of dyeing using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57192465A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4605635B2 (en) * | 2003-07-02 | 2011-01-05 | 日本化薬株式会社 | Azo compound, aqueous ink composition and colored body |
-
1981
- 1981-05-21 JP JP7571981A patent/JPS57192465A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57192465A (en) | 1982-11-26 |
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