JPH06104785B2 - Disazo dye mixture - Google Patents
Disazo dye mixtureInfo
- Publication number
- JPH06104785B2 JPH06104785B2 JP61224970A JP22497086A JPH06104785B2 JP H06104785 B2 JPH06104785 B2 JP H06104785B2 JP 61224970 A JP61224970 A JP 61224970A JP 22497086 A JP22497086 A JP 22497086A JP H06104785 B2 JPH06104785 B2 JP H06104785B2
- Authority
- JP
- Japan
- Prior art keywords
- dyeing
- disazo
- dye mixture
- dye
- present
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 25
- 239000000203 mixture Substances 0.000 title claims description 17
- 239000000975 dye Substances 0.000 claims description 44
- 238000002156 mixing Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 description 30
- 239000000835 fiber Substances 0.000 description 24
- 229920000728 polyester Polymers 0.000 description 15
- 238000000034 method Methods 0.000 description 11
- 229920002284 Cellulose triacetate Polymers 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000004744 fabric Substances 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 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004044 disperse dyeing Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 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
- 238000006068 polycondensation reaction Methods 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、ジスアゾ染料混合物に関するものであり、詳
しくは、構造的に類似する特定の２種以上のジスアゾ染
料を配合することにより、主に、ポリエステル繊維を染
色する際の吸尽性及び温感性に優れた青色系（ネービー
ブルー）の染料混合物に関する。Description: FIELD OF THE INVENTION The present invention relates to a disazo dye mixture, and more specifically, it is mainly prepared by blending two or more specific structurally similar disazo dyes to form a polyester. The present invention relates to a blue (navy blue) dye mixture which is excellent in exhaustion and warmth when dyeing a fiber.
従来の技術 下記一般式（Ｉ） （式中、Ｒは炭素数１〜４のアルキル基を表わす。）で
示されるジスアゾ染料は、近年提案されたポリエステル
繊維用の青色系（ネービーブルー）染料である（特開昭
59−96172号公報）。このジスアゾ染料は染色時におけ
る金属イオンの影響を受け難く、また、ポリエステル繊
維とセルローストリアセテート繊維の混合繊維を染色す
る場合の同色性に優れたものである。Conventional technology General formula (I) below The disazo dye represented by the formula (wherein R represents an alkyl group having 1 to 4 carbon atoms) is a blue (navy blue) dye for polyester fibers which has been proposed in recent years (Japanese Patent Laid-Open Publication No. Sho.
59-96172 publication). This disazo dye is not easily affected by metal ions at the time of dyeing, and is excellent in color uniformity when dyeing a mixed fiber of polyester fiber and cellulose triacetate fiber.
すなわち、従来の一般的なモノアゾ染料を用いてポリエ
ステル繊維の浸染染色を行なう場合、通常、染色浴中に
存在する金属イオンを、例えば、EDTAなどの金属封鎖剤
により封鎖する必要があるが、上記ジスアゾ染料の場合
には、金属封鎖剤の使用量を大幅に低減又は省略するこ
とができる。又、ポリエステル繊維とセルローストリア
セテート繊維の混合繊維を公知のモノアゾ染料を用いて
同時に染色した場合、一般的にセルローストリアセテー
ト繊維が赤味を呈する傾向があるが、上記ジスアゾ染料
の場合には、両繊維に対して同じ濃度及び色調で染色す
ることができる。That is, when performing dyeing dyeing of polyester fibers using a conventional general monoazo dye, usually, the metal ions present in the dyeing bath, for example, it is necessary to sequester with a sequestering agent such as EDTA, In the case of disazo dyes, the amount of sequestering agent used can be significantly reduced or omitted. Further, when a mixed fiber of polyester fiber and cellulose triacetate fiber is dyed at the same time with a known monoazo dye, the cellulose triacetate fiber generally tends to have a reddish color. Can be dyed with the same density and shade.
発明が解決しようとする問題点 上記の様に、前示一般式（Ｉ）で示されるジスアゾ染料
は、従来のモノアゾ染料に比べ、種々の優れた特色を持
つものであるが、一方では浸染染色を行なう場合のポリ
エステル繊維に対する吸尽性及び温感性がやや劣る欠点
があり、この点が実用上の問題点とされていた。Problems to be Solved by the Invention As described above, the disazo dye represented by the general formula (I) shown above has various excellent characteristics as compared with the conventional monoazo dye, but on the other hand, the dip dyeing In the case of carrying out, there was a drawback that the exhaustion and warm feeling to the polyester fiber were slightly inferior, and this point was regarded as a practical problem.
本発明は、上記事情に鑑みてなされたもので、前示一般
式（Ｉ）で示されるジスアゾ染料の特色を損なうことな
く、浸染染色におけるポリエステル繊維に対する吸尽性
及び温感性を改良することを目的とする。The present invention has been made in view of the above circumstances, and it is an object of the present invention to improve exhaustion and warmness to polyester fiber in dip dyeing without impairing the features of the disazo dye represented by the general formula (I). To aim.
問題点を解決するための手段 本発明者等は、種々検討を行なった結果、前示一般式
（Ｉ）で示される群より選ばれた構造の類似する少なく
とも２種のジスアゾ染料を配合して使用することによ
り、本発明の上記目的が達成されることを見い出し、本
発明を完成するに至った。Means for Solving the Problems As a result of various investigations, the present inventors have blended at least two disazo dyes having similar structures selected from the group represented by the general formula (I) shown above. It has been found that the above-mentioned objects of the present invention can be achieved by the use thereof, and the present invention has been completed.
本発明は、染料混合物であって、前示一般式（Ｉ）で示
される群より選ばれる少なくとも２種のジスアゾ染料を
配合しててなることを特徴とする。The present invention is a dye mixture, which is characterized by comprising at least two disazo dyes selected from the group represented by the general formula (I) shown above.
以下、本発明を詳細に説明する。Hereinafter, the present invention will be described in detail.
本発明では、前示一般式（Ｉ）で示される群より選ばれ
る少なくとも２種のジスアゾ染料を配合成分として用い
ることを必須の要件とするものであるが、代表的には２
種のジスアゾ染料である。その場合の配合割合は、通
常、一成分が20〜80重量部の範囲にあり、残りの成分が
80〜20重量部の範囲にある。In the present invention, it is essential to use at least two kinds of disazo dyes selected from the group represented by the general formula (I) shown above as a blending component, but typically 2
It is a kind of disazo dye. In that case, the mixing ratio is usually in the range of 20 to 80 parts by weight for one component, and the remaining components are
It is in the range of 80 to 20 parts by weight.
本発明の染料混合物を調整する方法としては、通常、各
々、ジアゾ化、カップリング反応により得られた前示一
般式（Ｉ）で示される複数のジスアゾ染料を所定量、配
合する方法、又は、ジアゾ化反応後の成分に、異なるカ
ップリング成分の混合物を所定の配合割合となるように
供給して、カップリング反応を行ない、所望のジスアゾ
染料混合物を得る方法が挙げられる。As a method for preparing the dye mixture of the present invention, usually, a method of blending a predetermined amount of a plurality of disazo dyes represented by the general formula (I) shown above obtained by diazotization and coupling reaction, respectively, or A method in which a mixture of different coupling components is supplied to the components after the diazotization reaction so as to have a predetermined mixing ratio and the coupling reaction is performed to obtain a desired disazo dye mixture can be mentioned.
本発明のジスアゾ染料混合物に用いる上記ジスアゾ染料
を合成する方法としては、例えば、ｐ−ニトロアニリン
をジアゾ化した後、２−アミノ−３−シアノ−チオフェ
ンとカップリングさせて得られる下記式 で示されるモノアゾ染料を更に、ジアゾ化し、次いで、
下記式 （Ｒは前記定義と同じ）で示されるアニリン類とカップ
リングさせることにより得ることができる。Examples of the method for synthesizing the above-mentioned disazo dye used in the disazo dye mixture of the present invention include the following formula obtained by diazotizing p-nitroaniline and then coupling with 2-amino-3-cyano-thiophene. The monoazo dye represented by is further diazotized, and then
The following formula It can be obtained by coupling with an aniline represented by (R is the same as the above definition).
本発明の染料混合物により染色しうる繊維としては、ポ
リエチレンテレフタレート、テレフタル酸と1,4−ビス
−（ヒドロキシメチル）シクロヘキサンとの重縮合物な
どよりなるポリエステル系繊維、又は、これらポリエス
テル系繊維と、例えば、セルローストリアセテート、木
綿、絹、羊毛などとの混合繊維が挙げられる。As the fibers that can be dyed with the dye mixture of the present invention, polyethylene terephthalate, polyester fibers composed of a polycondensation product of terephthalic acid and 1,4-bis- (hydroxymethyl) cyclohexane, or these polyester fibers, For example, mixed fibers with cellulose triacetate, cotton, silk, wool and the like can be mentioned.
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
する方法としては、通常の分散染料の染色方法が採用さ
れ、例えば、分散剤としてナフタレンスルホン酸とホル
ムアルデヒドとの縮合物などを使用して、水性媒質中に
分散させた染色浴又は、捺染糊を調整し、浸染又は捺染
を行なうことができる。更に、浸染の場合、高温染色
法、キャリャー染色法、サーモゾル染色法などの通常の
染色処理法を適用すれば、ポリエステル系繊維ないし
は、その混紡品に堅牢度の優れた染色を施することがで
きる。そして、本発明の染料混合物は、浸染に適用した
場合に、特に、吸尽性と温感性の効果が発揮されるので
好ましい。As a method for dyeing a polyester fiber using the dye mixture of the present invention, a usual disperse dyeing method is adopted, for example, using a condensate of naphthalenesulfonic acid and formaldehyde as a dispersant, an aqueous solution. Immersion or printing can be carried out by adjusting a dyeing bath or a printing paste dispersed in a medium. Further, in the case of dip dyeing, by applying an ordinary dyeing treatment method such as a high temperature dyeing method, a carrier dyeing method, and a thermosol dyeing method, it is possible to dye a polyester fiber or a blended product thereof with excellent fastness. . Further, the dye mixture of the present invention is particularly preferable when it is applied to dip dyeing because it exerts the effects of exhaustion and warmth.
実施例 次に、本発明を実施例によって更に具体的に説明する
が、本発明はその要旨を越えない限り、以下の実施例に
限定されるものではない。EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.
実施例１および２ 第１表に示すジスアゾ染料よりなる染料混合物を用い、
これを、ナフタレンスルホン酸−ホルムアルデヒド縮合
物0.5g及びメタクレゾールとシェファー酸のホルマリン
縮合物0.5gを含む水3lに分散させて染色浴を調整し、こ
れにポリエステル繊維100gを浸漬して130℃で60分間染
色を行なった。染色後の染布はソーピング、水洗及び乾
燥を行ない、染色性良好なネービーブルー色の染布を回
収した。Examples 1 and 2 Using a dye mixture consisting of the disazo dyes shown in Table 1,
This was dispersed in 3 liters of water containing 0.5 g of naphthalene sulfonic acid-formaldehyde condensate and 0.5 g of formalin condensate of metacresol and shefferic acid to prepare a dyeing bath, and 100 g of polyester fiber was dipped into this to prepare a dyeing bath at 130 ° C. Staining was performed for 60 minutes. The dyed fabric after dyeing was subjected to soaping, washing with water and drying to collect a navy blue dyeing fabric having good dyeability.
この染色テストにおける染布の吸尽性を求めると共に、
温感性テストを併せて実施した。その結果を第２表に示
す。In addition to seeking exhaustion of dyed cloth in this dyeing test,
A thermal sensitivity test was also conducted. The results are shown in Table 2.
比較例１および２ 実施例１の方法において、ジスアゾ染料として第１表に
示す１種の染料を用いて同様な染色を行った。その場合
の結果を第２表に示す。Comparative Examples 1 and 2 In the method of Example 1, similar dyeing was carried out using one kind of the dyes shown in Table 1 as the disazo dye. The results in that case are shown in Table 2.
0.1％リン酸のジメチルホルムアミド溶液を用いて染布
に染着した染料を溶解抽出して比色定量し、比較例１に
おける染着濃度を100として各染布の染着染料濃度を算
出し、相対値で示した。 The dye dyed on the dyeing cloth was dissolved and extracted with 0.1% phosphoric acid in dimethylformamide and colorimetrically determined, and the dyeing dye density of each dyeing cloth was calculated by setting the dyeing density in Comparative Example 1 to 100. It was shown as a relative value.
（注２）温感性 実施例における染色温度130℃を120℃に変えて全く同様
な染色を行ない、両染布の染料濃度（反射率）を測定
し、130℃の場合をベースとして比較した値（K/S値）で
示した。(Note 2) Warm-sensitivity A value obtained by measuring the dye concentration (reflectance) of both dyed cloths by changing the dyeing temperature of 130 ° C in the example to 120 ° C and measuring the dye density (reflectance) of both dyes, and comparing the values with 130 ° C as a base (K / S value).
発明の効果 本発明のジスアゾ染料混合物においては、前記のように
２種以上のジスアゾ染料を配合することにより、それ等
各々を単独で用いて、ポリエステル系繊維を染色する場
合に比べ、吸尽性及び温感性が飛躍的に向上する。した
がって、本発明のジスアゾ染料混合物は、ポリエステル
系繊維を染色するのに極めて適している。したがって
又、ポリエステル系繊維とセルローストリアセテート繊
維との混合繊維を染色するのにも有用である。Effects of the Invention In the disazo dye mixture of the present invention, by mixing two or more kinds of disazo dyes as described above, as compared with the case of dyeing a polyester fiber by using each of them alone, exhaustion And the warmth is dramatically improved. Therefore, the disazo dye mixture of the present invention is very suitable for dyeing polyester fibers. Therefore, it is also useful for dyeing mixed fibers of polyester fibers and cellulose triacetate fibers.
Claims (2)
示される群より選ばれる少なくとも２種のジスアゾ染料
を配合したことを特徴とするジスアゾ染料混合物。1. The following general formula (I): (In the formula, R represents an alkyl group having 1 to 4 carbon atoms.) A disazo dye mixture containing at least two disazo dyes selected from the group represented by:
る群より選ばれる２種のジスアゾ染料を配合成分とし、
それ等両成分の配合割合が20:80〜80:20（重量比）であ
ることを特徴とする特許請求の範囲第１項に記載のジス
アゾ染料混合物。2. A dye mixture containing two disazo dyes selected from the group represented by the general formula (I) shown above as a blending component,
The disazo dye mixture according to claim 1, characterized in that the mixing ratio of these two components is 20:80 to 80:20 (weight ratio).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61224970A JPH06104785B2 (en) | 1986-09-25 | 1986-09-25 | Disazo dye mixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61224970A JPH06104785B2 (en) | 1986-09-25 | 1986-09-25 | Disazo dye mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6381169A JPS6381169A (en) | 1988-04-12 |
| JPH06104785B2 true JPH06104785B2 (en) | 1994-12-21 |
Family
ID=16822061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61224970A Expired - Lifetime JPH06104785B2 (en) | 1986-09-25 | 1986-09-25 | Disazo dye mixture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06104785B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4937799B2 (en) * | 2007-03-16 | 2012-05-23 | 三和シヤッター工業株式会社 | Operation confirmation device for shutter water pressure release device |
| TWI577744B (en) * | 2012-03-26 | 2017-04-11 | Sumitomo Chemical Co | Composition and polarizing film |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5996172A (en) * | 1982-11-24 | 1984-06-02 | Gosei Senriyou Gijutsu Kenkyu Kumiai | Dis-azo dye for polyester fiber |
-
1986
- 1986-09-25 JP JP61224970A patent/JPH06104785B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6381169A (en) | 1988-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH02242862A (en) | Monoazo dye mixture | |
| JPS60255856A (en) | Yellow disperse dye mixture and dyeing process | |
| JP3806166B2 (en) | Blue disperse dye mixture and process for producing the same | |
| KR0168851B1 (en) | Disperse Dye Mixtures and Dyeing Methods Using the Same | |
| JPS59140264A (en) | Polyamide fiber dyeing or printing method | |
| JP3260492B2 (en) | Disperse dye mixture | |
| JPH06104785B2 (en) | Disazo dye mixture | |
| JPH09124966A (en) | Blue disperse dye mixture | |
| JPH0238465A (en) | Multi-component mixture of blue azo disperse dye for dyeing synthetic fiber | |
| JPH11302555A (en) | Disperse dye mixture | |
| JPH0551539A (en) | Dye composition and method of dyeing hydrophobic fiber by using it | |
| JPS5996167A (en) | Azo dye for synthetic fiber | |
| JPH1121465A (en) | Disperse dye composition | |
| JPH0150264B2 (en) | ||
| JP3032589B2 (en) | Disperse dye mixture | |
| JPH0674549B2 (en) | Dyeing method of composite fiber | |
| JPH06145548A (en) | Disperse dye mixture | |
| JPS5996166A (en) | Monoazo dye for synthetic fiber | |
| JP3006618B2 (en) | Monoazo dye | |
| JPS5944325B2 (en) | mixed dye composition | |
| JPS6243467B2 (en) | ||
| JPS61207467A (en) | Monoazo compounds and monoazo dyes | |
| JPH0124179B2 (en) | ||
| JPH0124178B2 (en) | ||
| JPH0349939B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |