JPS607073B2 - Dyeing method for hydrophobic fibers - Google Patents
Dyeing method for hydrophobic fibersInfo
- Publication number
- JPS607073B2 JPS607073B2 JP10852478A JP10852478A JPS607073B2 JP S607073 B2 JPS607073 B2 JP S607073B2 JP 10852478 A JP10852478 A JP 10852478A JP 10852478 A JP10852478 A JP 10852478A JP S607073 B2 JPS607073 B2 JP S607073B2
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Description
【発明の詳細な説明】
本発明は疎水性繊維特にポリエステル繊維またはアセテ
ート繊維を堅牢な黄色乃至緑黄色に染色する方法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for dyeing hydrophobic fibers, especially polyester fibers or acetate fibers, in a strong yellow to greenish-yellow color.
本発明の方法に用いる染料は次の一般式01で示される
モノアゾ染料である。The dye used in the method of the present invention is a monoazo dye represented by the following general formula 01.
(式中、Xは塩素原子,臭素原子又は沃素原子を表わし
Yは水素原子,塩素原子,臭素原子,沃素原子,メチル
基,メトキシ基,ニトロ基又はシアノ基を表わす。(In the formula, X represents a chlorine atom, a bromine atom, or an iodine atom, and Y represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a methoxy group, a nitro group, or a cyano group.
但しX,Yの一方は必ず沃素原子を表わす。Zは水素原
子、低級アルキル基あるいは低級アルコキシ低級アルキ
ル基を表わす。ここで低級アルキル及び低級アルコキシ
の意味は炭素数が1個乃至6個のものを表わすものとす
る。)本発明の方法に用いる染料に類似する染料がこれ
までに多数報告されているが、これら公知の染料は各々
特質があって、いずれも種々の欠点を持つている。However, one of X and Y always represents an iodine atom. Z represents a hydrogen atom, a lower alkyl group, or a lower alkoxy lower alkyl group. Here, lower alkyl and lower alkoxy refer to those having 1 to 6 carbon atoms. ) Many dyes similar to the dyes used in the method of the present invention have been reported, but each of these known dyes has its own characteristics and all have various drawbacks.
本発明者は、鋭意研究検討した結果、前記一般式(1}
で示される染料を用いて疎水性繊維、特にポリエステル
繊維またはアセテート繊維を染色及び捺染した場合に、
諸堅牢度が著しく優れ特に日光堅牢度,昇華堅牢度の著
しく優れた黄色乃至緑黄色の染色物が得られる事を見出
し、本発明を完成するに至った。As a result of intensive research and consideration, the present inventor has determined that the general formula (1)
When hydrophobic fibers, especially polyester fibers or acetate fibers, are dyed and printed using the dyes shown in
The present inventors have discovered that it is possible to obtain a yellow to greenish-yellow dyed product which has excellent fastness properties, particularly light fastness and sublimation fastness, and has completed the present invention.
本発明のカップリング成分は特公昭46一19716号
及び特公昭47一1854y獣こ記載されているが、そ
のジアゾ成分中には、本発明のジアゾ成分の如き沃素原
子によって置換されたフェニル基については記載がない
。The coupling component of the present invention is described in Japanese Patent Publication No. 46-19716 and Japanese Patent Publication No. 47-1854, and the diazo component contains a phenyl group substituted with an iodine atom such as the diazo component of the present invention. is not mentioned.
本発明の染料の特徴の一つは、このジアゾ成分即ち沃素
原子をアゾ基のオルソ位又は/およびパラ位に有する事
にあり、これらの染料は染着色ビルドアップ性が極めて
優れ、なおかつ昇華堅牢度の極めて優れたものである。One of the characteristics of the dyes of the present invention is that they have this diazo component, that is, an iodine atom, in the ortho and/or para positions of the azo group, and these dyes have extremely excellent color build-up properties and are fast to sublimation. The quality is extremely high.
この事は一般に染着性ビルドアップ性の向上と、昇華堅
牢度の向上とは相反する関係にあり、どちらかの点を蟻
牲にしなければならないか、もしくは両方をある程度の
水準に押えなければならないのが実情であるという事を
考えた場合、極めて注目すべきものである。以下に本発
明の染料と特公昭47−1854計号の染料との昇華堅
牢度の比較を示す。Generally speaking, there is a contradictory relationship between improving dye build-up properties and improving sublimation fastness, and either one of them must be sacrificed, or both must be kept to a certain level. Considering that the reality is that this is not the case, this is extremely noteworthy. A comparison of the sublimation fastness between the dye of the present invention and the dye of Japanese Patent Publication No. 47-1854 is shown below.
表中で示される染料の構造は式で示されるものとする。The structure of the dye shown in the table shall be shown by the formula.
前記の表から明らかなように、本願発明の染料は引例の
ものと比較して昇華堅牢度が優れていることがわかる。As is clear from the above table, it can be seen that the dyes of the present invention have superior sublimation fastness compared to those of the cited examples.
本発明の方法に用いる前記一般式‘1’の染料はたとえ
ば次の如くして得られる。下記式‘2)
で表わされるアミンをジアゾ化し、そして一般式‘3’
で表わされるカップリング成分とカップリングする事に
よって得られる。The dye of general formula '1' used in the method of the present invention can be obtained, for example, as follows. The amine represented by the following formula '2) is diazotized, and the general formula '3'
It can be obtained by coupling with a coupling component represented by
(×,Y,Zの意味は一般式‘1〕における意味と同じ
である。)一般式ゆで表わされるアミンは、下記式{4
}で表わされるアミン(式中Yは水素原子,塩素原子,
臭素原子,メチル基,メトキシ基,ェトロ基又はシアノ
基を表わす)を公知の方法で沃素化することにより、及
び下記式‘5}(式中Xは塩素原子又は臭素原子を表わ
す)で表わされるァミンを公知の方法で沃素化すること
により得られる。(The meanings of ×, Y, and Z are the same as in the general formula '1].) The amine represented by the general formula is represented by the following formula {4
} amine (where Y is a hydrogen atom, a chlorine atom,
(representing a bromine atom, methyl group, methoxy group, etro group or cyano group) by a known method, and a compound represented by the following formula '5} (wherein X represents a chlorine atom or a bromine atom) It can be obtained by iodizing amine by a known method.
更に一般式(2}において×,Yが共に沃素のものはア
ニリンを公知の方法によりジ沃素化する事により得られ
る。Furthermore, in the general formula (2}, both x and Y are iodine, which can be obtained by diiodinating aniline by a known method.
尚、本発明で使用されるカップリング成分{3’は公知
の方法(たとえばべリヒテ(Berichte)296
54(1896)記載の方法)により得られる。The coupling component {3' used in the present invention can be prepared by a known method (for example, Berichte 296).
54 (1896)).
即ち、アセト酢酸メチルェステルとシアノ酢酸メチルェ
ステル及び一般式‘61山N−Z (6}
(Zの意味は一般式(1},{3lにおける意味と同じ
である。That is, acetoacetic acid methyl ester, cyanoacetic acid methyl ester, and the general formula '61 N-Z (6} (the meaning of Z is the same as that in the general formula (1}, {3l).
)で表わされるアミンを加熱反応せしめ、冷却後水を加
えて希釈し、次いで塩酸又は硫酸を加えて酸性とし析出
する結晶を炉別して得られる。) is reacted by heating, diluted by adding water after cooling, and then acidified by adding hydrochloric acid or sulfuric acid, and the precipitated crystals are obtained by furnace separation.
本発明の方法に使用する一般式‘1}の染料は疎水性繊
維を染色するにあたって、染料を適当な分散剤と共に水
性媒質中で微細な粒子に紛砕して用いる。The dye of general formula '1} used in the method of the present invention is used by grinding the dye into fine particles in an aqueous medium together with a suitable dispersant when dyeing hydrophobic fibers.
分散化した梁剤はペースト状で使用するか、あるいはス
プレー乾燥法等によって粉末状として用いるのが好まし
い。この様にして得られた梁剤は繊維を浸潰した水性媒
体中で加圧下1060以上好ましくは110℃〜140
℃で染色するのが有利である。また、0一フエニルーフ
エノールやトリクロロベンゼン等のキャリャーの存在下
に比較的高温例えば水の沸騰状態で染色することもでき
る。It is preferable to use the dispersed beam agent in the form of a paste or in the form of a powder by spray drying or the like. The beam agent thus obtained is heated in an aqueous medium in which the fibers are soaked under pressure at a temperature of 1060°C or higher, preferably 110°C to 140°C.
It is advantageous to dye at °C. It is also possible to dye at a relatively high temperature, for example, in the boiling state of water, in the presence of a carrier such as O-1 phenylphenol or trichlorobenzene.
あるいはまた染料分散液を布にパツティングし150〜
230午Cで3町砂〜9現砂、間の乾燥処理をするいわ
ゆるサーモゾール染色法も可能である。一方、捺染を行
う場合には染料分散液を適当な糊と共に練り合わせ、こ
れを布にパッテイングしスチーミングまたはサーモゾー
ル方式で目的が蓬せられる。Alternatively, pat the dye dispersion onto the cloth and
It is also possible to use the so-called thermosol dyeing method, which involves drying between 3 town sand and 9 present sand at 230 pm C. On the other hand, in the case of printing, the dye dispersion is kneaded with a suitable paste, and the mixture is putted onto cloth and the desired purpose is achieved by steaming or thermosol method.
次に実施例をあげて本発明を更に詳しく説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例中部とあるのは重量部を意味する。実施例 1下
記式
の染料粉末1.2部を分散剤としてアルキルーナフタレ
ンースルホン酸とホルマリンの縮合物2.4部湿潤剤と
してポリアルキルナフタレンスルホン酸ソーダ0.4部
と共に水性媒体中で微細に砕き、分散化せしめる。"Example Middle" means parts by weight. Example 1 1.2 parts of a dye powder of the following formula was finely dispersed in an aqueous medium together with 2.4 parts of a condensate of alkylnaphthalene-sulfonic acid and formalin as a dispersant and 0.4 parts of sodium polyalkylnaphthalenesulfonate as a wetting agent. Crush it into pieces and disperse it.
この分散液をオレィル硫酸ソーダ1部を含む水400$
郭中に加えた梁液にポリエステル繊維(たとえばテトロ
ン)10礎都を浸潰して加圧容器中で130qoにおい
て60分間染色する。染色された繊維を常法により後処
理すれば堅牢度の良好な黄色の染色物が得られる。なお
本実施例に用いた染料は、たとえば次の如くして得られ
る。This dispersion was added to 400$ of water containing 1 part of sodium oleyl sulfate.
10 pieces of polyester fiber (for example, Tetron) are soaked in the liquid added to the dyeing process and dyed in a pressurized container at 130 qo for 60 minutes. If the dyed fibers are post-treated in a conventional manner, a yellow dyed product with good fastness can be obtained. The dye used in this example can be obtained, for example, as follows.
0−ニトローアニリンを公知の方法によって沃素化して
得られた2ーニトロー4ーョードーアニリン5.$部と
塩酸5部を乳鉢にてよく練り合せ、これに更に塩酸5部
及び水10の部を加えて、懸濁状態とし、氷冷下0〜3
℃にて趣硝酸ソーダ1.4部及び水1の部から成る溶液
を滴下する。2-nitro-4-yodoaniline obtained by iodizing 0-nitroaniline by a known method5. Thoroughly knead 5 parts of hydrochloric acid and 5 parts of hydrochloric acid in a mortar, add 5 parts of hydrochloric acid and 10 parts of water to form a suspension, and stir under ice cooling for 0 to 3 hours.
A solution consisting of 1.4 parts of sodium nitrate and 1 part of water is added dropwise at .
0〜3℃にて2時間櫨梓後スルフアミン酸を少量加えジ
アゾ液とする。After stirring for 2 hours at 0 to 3°C, a small amount of sulfamic acid is added to prepare a diazo solution.
一方、1一n−ブチルー3ーシアノ−4−メチル−6ー
ヒドロキシピリドー2ーオン4.群部、苛性ソーダ4.
0部、炭酸ソーダ5.4部、水300部を溶解しカップ
リング溶液とする。On the other hand, 1-n-butyl-3-cyano-4-methyl-6-hydroxypyrido-2-one 4. Gunbe, caustic soda 4.
0 parts, 5.4 parts of soda carbonate, and 300 parts of water were dissolved to prepare a coupling solution.
このカップリング溶液中に0℃〜10qoにてジアゾ液
を3世分で滴下する。Three portions of the diazo solution are added dropwise into this coupling solution at 0° C. to 10 qo.
同温度で30分嬢枠後、昇温せしめ約70qoにて30
分蝿梓後炉別、湯洗し、乾燥すれば黄色結晶として‘7
)式で表わされる染料8.群部が得られる。実施例 2
下記式
の染料粉末1.2部を実施例1と同様に分散剤を加えて
微粉砕して分散化せしめ、この分散液を市販のキャリア
‐(キャリアント323−東−邦化学製品)5部、界面
活性剤(モノゲン第一工業製薬製品)5部及び水150
碇部より成る染格に加えテトロン製織物100部を浸潰
して30分間で梁俗を沸点まで上昇せしめ、この温度で
60分間保持する。After 30 minutes at the same temperature, raise the temperature to approximately 70 qo for 30 minutes.
If you wash it with hot water and dry it, it will turn into yellow crystals.'7
) Dye represented by formula 8. A group part is obtained. Example 2 1.2 parts of a dye powder of the following formula was dispersed by adding a dispersant and finely pulverized in the same manner as in Example 1, and the dispersion was mixed with a commercially available carrier (Carrierant 323-Toho Chemical Products). ) 5 parts, surfactant (Monogen Daiichi Kogyo Pharmaceutical Products) 5 parts, and water 150 parts
In addition to the dyeing consisting of the anchor part, 100 parts of the Tetron fabric were soaked to raise the liangsu to the boiling point in 30 minutes and held at this temperature for 60 minutes.
更に染色物を常法により後処理すれば、堅牢度の良好な
緑黄色の染色物が得られる。本実施例に用いた染料は次
の如くして得られる。Further, if the dyed product is post-treated by a conventional method, a green-yellow dyed product with good fastness can be obtained. The dye used in this example can be obtained as follows.
0−クロルーアニリンを公知の方法で沃素化して得られ
た2−クロル4−ヨードーアニリン5.1部、塩酸1の
部、水10碇部を混ぜ約60ooで30分燈梓する。5.1 parts of 2-chloro-4-iodoaniline obtained by iodizing 0-chloroaniline by a known method, 1 part of hydrochloric acid, and 10 parts of water were mixed and heated at about 60 oo for 30 minutes.
冷却し0〜3℃にて亜硝酸ソーダ1.4部と水1碇部か
ら成る溶液を30分で滴下し0〜300で1時間境梓後
スルファミン酸少量を加えてジアゾ液とする。一方1−
(r−メトキシープロピル)−3ーシアノー4ーメチル
−6−ヒドロキシピリド−2ーオン4.5部、酢酸ソー
ダ15部、水30の部を溶解しカップリング液とする。After cooling, a solution consisting of 1.4 parts of sodium nitrite and 1 part of water was added dropwise at 0 to 3° C. over 30 minutes, and after stirring for 1 hour at 0 to 300° C., a small amount of sulfamic acid was added to prepare a diazo solution. On the other hand 1-
A coupling liquid was prepared by dissolving 4.5 parts of (r-methoxypropyl)-3-cyano-4-methyl-6-hydroxypyrid-2-one, 15 parts of sodium acetate, and 30 parts of water.
このカップリング液に0℃〜500にてジアゾ液を60
分で滴下する。同温度で30分櫨梓後昇温せしめ約70
q Cにて1時間酒梓後炉別、傷洗し、乾燥すれば黄色
結晶として(8}式で表わされる染料9.6部が得られ
る。実施例 3
下記式
の染料を用いて実施例1あるいは実施例2と同様にして
ポリエステル繊維を良好な堅牢度をもつ黄色に染色する
事ができる。Add 60% diazo solution to this coupling solution at 0°C to 500°C.
Drips in minutes. After 30 minutes at the same temperature, raise the temperature to approx.
After brewing the sake at qC for 1 hour, removing it from the oven, washing the scratches, and drying, 9.6 parts of the dye represented by the formula (8) is obtained as yellow crystals.Example 3 An example was carried out using the dye of the following formula. Polyester fibers can be dyed yellow with good fastness in the same manner as in Example 1 or Example 2.
またこの染料を捺染に用いるには実施例1と同様にして
分散化した後、次の組成により色糊を調整する。To use this dye for textile printing, it is dispersed in the same manner as in Example 1, and then a colored paste is prepared according to the following composition.
■式の分散化染料 1の部微温湯
27.8部カルポキシメ
チルセルローズ系糊剤 6碇部酒石酸
0.2部均梁剤(ィンプルーバー800
) 2部(※横浜ポリマー研究所製)計
10碇部
この色糊を用いて印漆、乾燥後175℃、5分の過熱蒸
気によるスチーミングを行ない次いで水洗脱糊、還元洗
浄、水洗乾燥する。■ Formula dispersed dye 1 part lukewarm water
27.8 parts Carpoxymethyl cellulose glue 6 parts Tartaric acid
0.2 parts leveling agent (Improver 800
) 2 parts (*manufactured by Yokohama Polymer Research Institute) total
10 anchor parts Using this color paste, ink lacquer, drying, steaming with superheated steam at 175°C for 5 minutes, washing with water, descaling, reduction washing, washing with water and drying.
また、この染料をサーモゾール染色法に用いるには実施
例1と同様にして分散化後、パッド槽に分散溶解した染
料10夕/そとマィグレーション防止剤としてアルギン
酸ソーダ1夕/そを加えてパッド液とし、ポリエステル
/木綿混紡布を室温でパッドして、重量増加率65%に
絞る。To use this dye in the thermosol dyeing method, after dispersing it in the same manner as in Example 1, add 10 parts of the dispersed and dissolved dye to a pad tank and add 1 part of sodium alginate as a migration inhibitor. A pad solution is used to pad a polyester/cotton blend cloth at room temperature, and the weight increase rate is reduced to 65%.
中間乾燥を行なった後、200q0、9町砂の乾熱固着
を行なう。After performing intermediate drying, dry heat fixation of 200q0, 9 town sand is performed.
次いで還元洗浄、水洗乾燥する。上記、捺染及びサーモ
ゾール法、いずれにおいても諸堅牢度の優れた、黄色の
染色物が得られた。ここで用いた染料は実施例1で用い
た染料を製造する場合に用いた1−n−ブチルー3−シ
アノー4ーメチル−6ーヒドロキシーピリド−2ーオン
のかわりに1−エチル−3−シアノ−4−メチル−6−
ヒドロキシーピリド−2−オンを用いて実施例1と同様
にして得る事ができる。実施例1で使われた染料1.友
邦のかわりに、下記一般式で表わされ、そのX,Y,Z
が次表で示される構造をもつ染料1.2部をそれぞれ使
用して実施例1と同じ方法を適用する事により、次表右
欄に示される色調の染色物がいずれも良好な堅牢度をも
って得られる。Next, it is subjected to reduction cleaning, washing with water and drying. In both the above-mentioned printing and thermosol methods, a yellow dyed product with excellent fastness was obtained. The dye used here was 1-ethyl-3-cyano instead of 1-n-butyl-3-cyano-4-methyl-6-hydroxy-pyrid-2-one used in producing the dye used in Example 1. -4-methyl-6-
It can be obtained in the same manner as in Example 1 using hydroxypyrid-2-one. Dye used in Example 1 1. Instead of Yukuni, it is represented by the following general formula, and its X, Y, Z
By applying the same method as in Example 1 using 1.2 parts of each dye having the structure shown in the following table, dyed products with the tones shown in the right column of the following table all had good fastness. can get.
次に本願発明実施例の染料のm.p.又は入maxを以
下の表に示す。Next, the m. p. Or input max is shown in the table below.
Claims (1)
料を用いる事を特徴とする疎水性繊維の染色法。 ▲数式、化学式、表等があります▼ (式中Xは塩素原子,臭素原子又は沃素原子を表わし
、Yは水素原子,塩素原子,臭素原子,沃素原子,メチ
ル基,メトキシ基,ニトロ基又はシアノ基を表わす。 但しX,Yの一方は必ず沃素原子を表わす。Zは水素原
子,低級アルキル基あるいは低級アルコキシ低級アルキ
ル基を表わす。ここで低級アルキル及び低級アルコキシ
の意味は炭素数が1個乃至6個のものを表わすものとす
る。)[Scope of Claims] 1. A method for dyeing hydrophobic fibers, characterized by using a water-insoluble monoazo dye represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X represents a chlorine atom, a bromine atom, or an iodine atom, and Y represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a methoxy group, a nitro group, or a cyano atom. Represents a group. However, one of X and Y always represents an iodine atom. Z represents a hydrogen atom, a lower alkyl group, or a lower alkoxy lower alkyl group. Here, lower alkyl and lower alkoxy mean a group having 1 or more carbon atoms. (It represents six things.)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10852478A JPS607073B2 (en) | 1978-09-06 | 1978-09-06 | Dyeing method for hydrophobic fibers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10852478A JPS607073B2 (en) | 1978-09-06 | 1978-09-06 | Dyeing method for hydrophobic fibers |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5536350A JPS5536350A (en) | 1980-03-13 |
JPS607073B2 true JPS607073B2 (en) | 1985-02-22 |
Family
ID=14486979
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10852478A Expired JPS607073B2 (en) | 1978-09-06 | 1978-09-06 | Dyeing method for hydrophobic fibers |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS607073B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4329762A1 (en) * | 1993-09-03 | 1995-03-09 | Cassella Ag | Process for dyeing polyester and textile materials containing polyester |
-
1978
- 1978-09-06 JP JP10852478A patent/JPS607073B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS5536350A (en) | 1980-03-13 |
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