JPH0460507B2 - - Google Patents
Info
- Publication number
- JPH0460507B2 JPH0460507B2 JP60044697A JP4469785A JPH0460507B2 JP H0460507 B2 JPH0460507 B2 JP H0460507B2 JP 60044697 A JP60044697 A JP 60044697A JP 4469785 A JP4469785 A JP 4469785A JP H0460507 B2 JPH0460507 B2 JP H0460507B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- formula
- parts
- weight
- fastness
- 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
- 239000000203 mixture Substances 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000012209 synthetic fiber Substances 0.000 claims description 7
- 229920002994 synthetic fiber Polymers 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000004744 fabric Substances 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 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
- 239000006185 dispersion Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- -1 monoazo compound Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
産業上の利用分野
本発明は下式(1)
で示される染料30〜70重量％と、下式(2)で示され
る染料30〜70重量％
及び必要に応じ下式(3)
（式中(3)中X1、X2はニトロ基、シアノ基又は
ハロゲン原子を表わす。）
で示される染料０〜30重量％を配合した染料混合
物及びその染料混合物を用いて合成繊維又は半合
成繊維を染色する方法に関する。
従来の技術
本発明の式(1)及び式(2)の染料は、特開昭59−
197464に記載されていて公知であり、また式(3)で
示される染料は例えば下式(4)〜(8)
で示される染料としては以前より市販されてい
る。
また、これら式(4)〜(8)の青色〜ネービー色染料
類似染料として下式(9)
で示される染料は需要が大きく、古くよりよく知
られた染料である。
発明が解決しようとする問題点及び解決するため
の手段
本発明に係る上記式(1)及び(2)で示される染料
は、各種堅牢度、特に耐光堅牢度が優れているも
のの、染色性が従来のアゾ系青色染料例えば上記
式(9)などの染料に比較して劣つており、従来のア
ゾ染料と同一量の染料で染色した時、合成繊維特
にポリエステル繊維上での染色濃度が低いという
欠点がわかつた。
また式(9)で示される染料（カラーインデツクス
ブルー79）は耐光堅牢度及びカラーバリユーが満
足できるものでなく、その他式(4)〜(8)の染料は昇
華堅牢度においても充分でなかつた。
本発明者らは合成繊維、特にポリエステル繊維
を染色または捺染した場合、染色物の諸堅牢度は
もとより、染着率が大きくビルドアツプ性のすぐ
れた青色〜ネービ色染料を鋭意探索した結果、式
(1)で示される染料（30〜70重量％）と、式(2)で示
される染料（30〜70重量％）を混合すれば、式(1)
または式(2)の染料だけで染色したときに比べ染着
率が著しく向上することがわかつた。
またその際、式(3)で示される染料（１〜30重量
％）をさらに混合すれば、ビルドアツプ性が向上
することもわかつた。
本発明染料混合物に使用される前記式(1)又は(2)
で示されるジスアゾ染料は公知方法に従い、下記
式
（式中、Ｘは水素原子またはニトロ基）
で示されるアミン類をジアゾ化し、下記式
で示されるアミノチオフエン類とカツプリングさ
せ得られた下記式
（式中、Ｘは水素原子又はニトロ基）
で示されるモノアゾ化合物をジアゾ化し、下記
で示されるＮ−エチル−Ｎ−シアノエチルアニリ
ンとカツプリングさせることにより、製造するこ
とが出来る。
本発明の実施にあたつては、配合に供する各染
料のプレスケーキを適当な分散剤、例えばナフタ
レンスルホン酸とホルマリンとの縮合物などを用
いて水性媒体中で微粒化分散し、そのまま粉末状
にあるいはスプレー乾燥法等により粉末状とした
後、所望の割合に配合して青色〜ネービ色染料組
成物とするのが有利である。
この様にして得られた本発明の染料混合物を用
いてポリエステル系繊維を染色するには、加圧下
105℃以上、好ましくは110〜140℃で染色する方
法。ｏ−フエニルフエノール等のキヤリアーの存
在下に比較的高温、例えば水の沸点で染色する方
法あるいは染料分散液を布にパデイングし、150
〜240℃で30〜60秒乾熱処理を行う方法（サーモ
ゾル法）等があげられる。
一方、捺染を行う場合には、染料組成物をグア
ガムやローカストビームガム等の適当な糊剤と共
に練り合せこれを布に印捺して、スチーミング又
はサーモゾル法で処理して目的を達する。
作用及び効果
式(1)及び式(2)で示される染料は各々単独では、
ポリエステル布に対する親和性が小さく、実用的
な染色濃度が得られがたかつた。すなわち、５％
owf以上での染色時の濃度不足、又、温度感受性
（例えば120℃染色時と130℃染色時の染色濃度）
が大きいため、実用化が出来なかつた。ところが
本発明のように混合物染料とすることによりこれ
らの欠点が解決されると共に、従来より用いられ
ている染料（例えばカラーインデツクスブルー
79）などよりも堅牢度も良く、PH感受性が小さい
という高品位の染料が得られた。
これらの具体的な効果を表に示す。
Industrial Application Field The present invention is based on the following formula (1) 30 to 70% by weight of the dye represented by and 30 to 70% by weight of the dye represented by the following formula (2) and the following formula (3) as necessary (In the formula (3), X 1 and X 2 represent a nitro group, a cyano group, or a halogen atom.) A dye mixture containing 0 to 30% by weight of the dye represented by the formula (3) and a synthetic fiber or semi-woven fabric using the dye mixture This invention relates to a method for dyeing synthetic fibers. Prior Art The dyes of formulas (1) and (2) of the present invention are
197464 and is publicly known, and the dye represented by the formula (3) is, for example, the dye represented by the following formulas (4) to (8). The dye represented by has been commercially available for some time. In addition, the following formula (9) is used as a dye similar to the blue to navy dyes of these formulas (4) to (8). The dye shown is in great demand and has been well known for a long time. Problems to be Solved by the Invention and Means for Solving the Problems The dyes represented by the above formulas (1) and (2) according to the present invention are excellent in various fastnesses, especially light fastness, but have poor dyeability. It is inferior to conventional azo blue dyes, such as dyes of formula (9) above, and when dyed with the same amount of dye as conventional azo dyes, the dyeing density on synthetic fibers, especially polyester fibers, is low. I found out the shortcomings. Furthermore, the dye represented by formula (9) (color index blue 79) does not have satisfactory light fastness and color value, and the other dyes of formulas (4) to (8) do not have sufficient sublimation fastness. Nakatsuta. The present inventors have diligently searched for blue to navy dyes that have a high dyeing rate and excellent build-up properties when dyeing or printing synthetic fibers, especially polyester fibers, as well as various fastnesses of dyed products.
If the dye represented by (1) (30 to 70% by weight) and the dye represented by formula (2) (30 to 70% by weight) are mixed, formula (1)
It was also found that the dyeing rate was significantly improved compared to when dyeing with the dye of formula (2) alone. It was also found that if the dye represented by formula (3) (1 to 30% by weight) is further mixed at that time, the build-up property can be improved. The above formula (1) or (2) used in the dye mixture of the present invention
The disazo dye represented by is prepared by the following formula according to a known method. (In the formula, X is a hydrogen atom or a nitro group) By diazotizing the amines shown below, The following formula obtained by coupling with aminothiophenes shown by (In the formula, X is a hydrogen atom or a nitro group) A monoazo compound represented by the following is diazotized, and the following It can be produced by coupling with N-ethyl-N-cyanoethylaniline shown in In carrying out the present invention, the press cake of each dye to be blended is micronized and dispersed in an aqueous medium using a suitable dispersant, such as a condensate of naphthalene sulfonic acid and formalin, and then directly powdered. It is advantageous to form the dye into a powder by drying or spray drying, and then blend it in a desired proportion to form a blue to navy dye composition. In order to dye polyester fibers using the dye mixture of the present invention obtained in this way, the method is carried out under pressure.
A method of dyeing at 105°C or higher, preferably 110-140°C. A method of dyeing at a relatively high temperature, for example, the boiling point of water, in the presence of a carrier such as o-phenylphenol, or by padding the fabric with a dye dispersion,
Examples include a method of performing dry heat treatment at ~240°C for 30 to 60 seconds (thermosol method). On the other hand, in the case of printing, the dye composition is kneaded with a suitable thickening agent such as guar gum or locust beam gum, and the mixture is printed on cloth and treated by steaming or thermosol method to achieve the purpose. Actions and Effects The dyes represented by formula (1) and formula (2) each have the following effects when used alone:
It had a low affinity for polyester fabrics, making it difficult to obtain a practical dyeing density. i.e. 5%
Insufficient density when staining at owf or higher, and temperature sensitivity (e.g. staining density when staining at 120℃ and 130℃)
Due to the large size, it was not possible to put it into practical use. However, by using a mixture dye as in the present invention, these drawbacks can be solved, and dyes that have been used conventionally (for example, Color Index Blue) can be used.
79), a high-quality dye with better fastness and less PH sensitivity was obtained. These specific effects are shown in the table.
【表】【table】
【表】
実施例
例中の部は重量部を示し、％は重量％を示す。
実施例 １
下式(A)の染料５部と下式(B)の染料５部、及びデ
モールＮ（花王アトラス社製品）20部及び水30部
を混合し、
微粒化した。乾燥し、タイプ品を得た。
このタイプ品６部を水200部に分散した液にポ
リエステル織物100部を浸漬し、加圧下130℃で１
時間染色した。ついでハイドロサルフアイト20
部、苛性ソーダ20部を含む水1000部に染色布を浸
漬した後、水洗乾燥したところ、濃紺色の染色物
が得られた。
この染色布の耐光堅牢度（JIS L0842−1971に
よる。以下の実施例も同じ）６−７級、昇華堅牢
度４級（JIS L0879−1975（180℃30秒）による。
以下実施例も同じ）、AATCCＡ法洗濯堅牢度
３〜４級、水堅牢度５級（スミテツクスレジン
UN−１による樹脂加工後にJIS L0846−1976（Ｂ
法 16時間）による。以下の実施例も同じ）であ
つた。
実施例 ２
実施例１の式(A)の染料５部、式(B)の染料４部と
下記式(C)の染料１部及びデモールＣ（花王アトラ
ス社製品）20部及び水30部を混合し、
微粒化した。乾燥し、タイプ品を得た。
上記タイプ品６部を実施例１と同様にして染色
したところ、濃紺色の染色布を得た。
この染色布の耐光堅牢度６−７級、昇華堅牢度
４級、AATCCＡ法洗濯堅牢度３−４級、水堅
牢度５級であつた。
実施例 ３
実施例１の式(A)の染料５部、式(B)の染料３部と
下式(D)の染料２部、及びデモールN2部及び水18
部を混合し微粒化することによりペースト状の染
料混合物を得た。
この染料混合物３部、メイプロガムNP
（Meyhall社製品）12％水溶液60部、塩素酸ソー
ダ0.5部及び水36.5部よりなる色糊をポリエステ
ル布に印捺し、80℃で中間乾乾燥後、175℃で７
分間高圧蒸気でスチーミングした。次いで水洗、
還元洗浄することにより青色の染色布が得られ
た。
この染色布の耐光堅牢度７級、昇華堅牢度４
級、AATCCＡ法洗濯堅牢度４級、水堅牢度５
級であつた。
実施例 ４
実施例１の式(A)の染料５部、式(B)の染料３部と
下式(E)の染料２部をデモールＮ（花王アトラス社
製品）５部と水15部と混合し、微粒化すること
により、液状染料混合物を得た。
上記液状染料混合物５部、クエン酸0.5部及び
アルギン酸ソーダ0.2部を水100部に分散し、分散
液にポリエステル加工糸布をパデイングした後、
80℃にて中間乾燥した。210℃、１分間乾熱加熱
（サーモゾール染色）をすることにより染色し、
続いて還元洗浄、水洗をすることにより濃紺色の
染色布が得られた。この染色布の耐光堅牢度は６
−７級、昇華堅牢度４級、AATCC法洗濯堅牢
度４級、水堅牢度５級であつた。[Table] Examples In the examples, parts indicate parts by weight, and % indicates weight %. Example 1 5 parts of the dye of the formula (A) below, 5 parts of the dye of the formula (B) below, 20 parts of Demol N (product of Kao Atlas Co., Ltd.) and 30 parts of water were mixed, Atomized. It was dried to obtain a type product. 100 parts of polyester fabric was immersed in a solution in which 6 parts of this type was dispersed in 200 parts of water, and 100 parts of polyester fabric was immersed in the solution at 130°C under pressure.
Time stained. Next, Hydrosulfite 20
When the dyed cloth was immersed in 1,000 parts of water containing 20 parts of caustic soda, washed with water and dried, a dark blue dyed product was obtained. The light fastness of this dyed fabric (according to JIS L0842-1971; the same applies to the following examples) is grade 6-7, and the sublimation fastness is grade 4 (according to JIS L0879-1975 (180°C for 30 seconds)).
The same applies to the examples below), AATCCA washing fastness grade 3 to 4, water fastness grade 5 (Sumitex Resin
JIS L0846-1976 (B) after resin processing by UN-1
16 hours). The same applies to the following examples). Example 2 5 parts of the dye of the formula (A) of Example 1, 4 parts of the dye of the formula (B), 1 part of the dye of the following formula (C), 20 parts of Demol C (product of Kao Atlas Co., Ltd.) and 30 parts of water were added. mix, Atomized. It was dried to obtain a type product. Six parts of the above-mentioned type product were dyed in the same manner as in Example 1 to obtain a dark blue dyed cloth. The dyed fabric had a light fastness of 6-7, a sublimation fastness of 4, a washing fastness of AATCCA method of 3-4, and a water fastness of 5. Example 3 5 parts of dye of formula (A) of Example 1, 3 parts of dye of formula (B), 2 parts of dye of formula (D) below, 2 parts of Demol N and 18 parts of water
A paste-like dye mixture was obtained by mixing and atomizing the parts. 3 parts of this dye mixture, Maypro Gum NP
(Meyhall product) A color paste consisting of 60 parts of a 12% aqueous solution, 0.5 parts of sodium chlorate, and 36.5 parts of water was printed on polyester cloth, and after drying at 80°C, it was dried at 175°C for 7 days.
Steamed with high pressure steam for minutes. Then wash with water,
A blue dyed cloth was obtained by reduction washing. The light fastness of this dyed cloth is 7th grade, and the sublimation fastness is 4th grade.
Class: AATCCA washing fastness level 4, water fastness level 5
It was classy. Example 4 5 parts of dye of formula (A), 3 parts of dye of formula (B) and 2 parts of dye of formula (E) of Example 1 were mixed with 5 parts of Demol N (product of Kao Atlas Co., Ltd.) and 15 parts of water. mixing and atomizing A liquid dye mixture was obtained. After dispersing 5 parts of the above liquid dye mixture, 0.5 parts of citric acid, and 0.2 parts of sodium alginate in 100 parts of water, and padding the dispersion with polyester processed yarn cloth,
Intermediate drying was performed at 80°C. Dye by dry heat heating (thermosol dyeing) at 210℃ for 1 minute,
Subsequently, by reduction washing and washing with water, a dark blue dyed cloth was obtained. The light fastness of this dyed cloth is 6
-7 grade, sublimation fastness grade 4, AATCC washing fastness grade 4, and water fastness grade 5.
Claims (1)
重量％ （式(3)中、X1、X2は各々独立にニトロ基、シ
アノ基、ハロゲン原子を表わす。） からなる合成繊維用染料混合物。 ２ 下式(1) で示される染料30〜70重量％と、 下式(2)で示される染料30〜70重量％ 及び必要に応じて、下式(3)で示される染料０〜30
重量％ （式(3)中、X1、X2は各々独立にニトロ基、シ
アノ基、ハロゲン原子を表わす。） からなる染料混合物を用いて、合成繊維または半
合成繊維を染色又は捺染する方法。[Claims] 1. The following formula (1) 30 to 70% by weight of the dye represented by and 30 to 70% by weight of the dye represented by the following formula (2) and, if necessary, a dye represented by the following formula (3) 0 to 30
weight% (In formula (3), X 1 and X 2 each independently represent a nitro group, a cyano group, or a halogen atom.) A dye mixture for synthetic fibers. 2 Below formula (1) 30 to 70% by weight of the dye represented by and 30 to 70% by weight of the dye represented by the following formula (2) and, if necessary, a dye represented by the following formula (3) 0 to 30
weight% (In formula (3), X 1 and X 2 each independently represent a nitro group, a cyano group, or a halogen atom.) A method of dyeing or printing synthetic fibers or semi-synthetic fibers using a dye mixture consisting of the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044697A JPS61204274A (en) | 1985-03-08 | 1985-03-08 | Dye mixture for synthetic fiber, and dyeing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044697A JPS61204274A (en) | 1985-03-08 | 1985-03-08 | Dye mixture for synthetic fiber, and dyeing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61204274A JPS61204274A (en) | 1986-09-10 |
| JPH0460507B2 true JPH0460507B2 (en) | 1992-09-28 |
Family
ID=12698606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60044697A Granted JPS61204274A (en) | 1985-03-08 | 1985-03-08 | Dye mixture for synthetic fiber, and dyeing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61204274A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008179917A (en) * | 2007-01-25 | 2008-08-07 | Teijin Fibers Ltd | Method for producing colored polyester fabric, colored polyester fabric and clothing |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58201855A (en) * | 1982-05-19 | 1983-11-24 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Mixed dye for polyester fiber |
| JPS59197464A (en) * | 1983-04-25 | 1984-11-09 | Mitsui Toatsu Chem Inc | Disazo dye for synthetic fiber |
-
1985
- 1985-03-08 JP JP60044697A patent/JPS61204274A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58201855A (en) * | 1982-05-19 | 1983-11-24 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Mixed dye for polyester fiber |
| JPS59197464A (en) * | 1983-04-25 | 1984-11-09 | Mitsui Toatsu Chem Inc | Disazo dye for synthetic fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61204274A (en) | 1986-09-10 |
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