JPH0711588A - Dyeing of fiber material with benzodifuranone-type disperse dye - Google Patents

Dyeing of fiber material with benzodifuranone-type disperse dye

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Publication number
JPH0711588A
JPH0711588A JP5150373A JP15037393A JPH0711588A JP H0711588 A JPH0711588 A JP H0711588A JP 5150373 A JP5150373 A JP 5150373A JP 15037393 A JP15037393 A JP 15037393A JP H0711588 A JPH0711588 A JP H0711588A
Authority
JP
Japan
Prior art keywords
buffer solution
dyeing
benzodifuranone
disperse dye
fiber material
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.)
Pending
Application number
JP5150373A
Other languages
Japanese (ja)
Inventor
Osayuki Katsuta
修之 勝田
Shinichi Yabushita
伸一 藪下
Shuhei Hashizume
修平 橋爪
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP5150373A priority Critical patent/JPH0711588A/en
Publication of JPH0711588A publication Critical patent/JPH0711588A/en
Pending legal-status Critical Current

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Abstract

PURPOSE:To obtain an industrially advantageous dyeing process free from troubles of unlevel dyeing, change of hue, etc., by dyeing especially a hydrophobic fiber with a benzodifuranone-type disperse dye in excellent dyeability. CONSTITUTION:A fiber material is dyed with a benzodifuranone-type disperse dye in a bathing bath of pH 3-6.5 consisting of ClarkLubs buffer solution, Sphirensen buffer solution, Kolthoff buffer solution, Michaelis buffer solution (except for buffer solutions containing acetic acid and sodium acetate), Mclvalne buffer solution or Walpole buffer solution (except for buffer solutions containing acetic acid and sodium acetate) or their diluted solutions.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明はベンゾジフラノン系分散
染料を用いて、繊維材料、特に疎水性繊維材料を染色す
る方法に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for dyeing a fiber material, particularly a hydrophobic fiber material, with a benzodifuranone type disperse dye.

【0002】[0002]

【従来技術および発明が解決しようとする課題】例えば
特開昭60-152567 号公報、同52-109526 号公報、同56-1
22869 号公報、特開平3-72571 号公報などには種々のベ
ンゾジフラノン化合物が特に疎水性繊維の染色に分散染
料として有用であることが記載されている。しかしこれ
らのベンゾジフラノン系分散染料を使用して染色を行っ
た場合、染色工程における条件によって染色濃度が低下
する、あるいは色相が変化するなどの問題が発生してお
り、その解決が望まれている。
Prior Art and Problems to be Solved by the Invention For example, JP-A-60-152567, JP-A-52-109526 and JP-A-56-1.
22869 and Japanese Patent Application Laid-Open No. 3-72571 disclose that various benzodifuranone compounds are useful as disperse dyes particularly for dyeing hydrophobic fibers. However, when these benzodifuranone-based disperse dyes are used for dyeing, problems such as a decrease in dyeing density and a change in hue occur depending on the conditions in the dyeing process, and their solution is desired.

【0003】また、特開昭56-45960号公報には、分散染
料を用い、染浴のpHを弱酸性に維持することができるよ
うな緩衝溶液を使用して疎水性繊維染色する方法が記載
されている。しかしながら、たとえば、酢酸と酢酸ソー
ダ、硫酸と硫酸ソーダのような同系統の酸とその塩から
なる緩衝溶液は十分な緩衝効果を得ることができないと
して、硫酸と有機酸塩からなる緩衝溶液などが提案され
ている。
Further, JP-A-56-45960 describes a method of dyeing a hydrophobic fiber using a disperse dye and a buffer solution capable of maintaining the pH of a dye bath at a weak acidity. Has been done. However, for example, a buffer solution composed of an acid of the same system and a salt thereof such as acetic acid and sodium acetate and sulfuric acid and sodium sulfate cannot obtain a sufficient buffering effect, and a buffer solution composed of sulfuric acid and an organic acid salt is not available. Proposed.

【0004】本発明者らは、ベンゾジフラノン系分散染
料で疎水性繊維材料、特にポリエステル繊維を優れた染
色性で染色し、かつ不均染、色相変化を起こさない工業
的有利な染色法を見いだすべく鋭意検討の結果、本発明
を完成するにいたった。
The inventors of the present invention should find an industrially advantageous dyeing method for dyeing a hydrophobic fiber material, particularly polyester fiber with an excellent dyeability with a benzodifuranone-based disperse dye, and causing no uneven dyeing or hue change. As a result of intensive studies, the present invention has been completed.

【0005】[0005]

【課題を解決するための手段】本発明は、ベンゾジフラ
ノン系分散染料を用い、クラークラブズ(Clark-Lubs)
の緩衝溶液、シェーレンシェン(Sφrensen) の緩衝溶
液、コルソッフ(Kolthoff) の緩衝溶液、ミハイル(Mic
haelis) の緩衝溶液(ただし、酢酸および酢酸ソーダを
含有する緩衝溶液を除く。) 、マックイベイン(McIvain
e)の緩衝溶液もしくはワルポール(Walpole) の緩衝溶液
(ただし、酢酸および酢酸ソーダを含有する緩衝溶液を
除く。) またはそれらの希釈液であって、pHが3〜6.
5である染浴中で染色することを特徴とする繊維材料の
染色方法を提供する。
The present invention uses a benzodifuranone-based disperse dye and uses Clark-Lubs.
Buffer solution, Sφrensen buffer solution, Kolthoff buffer solution, Mihail (Mic
haelis) buffer solution (excluding buffer solution containing acetic acid and sodium acetate), McIvain (McIvain
e) buffer solution or Walpole buffer solution (excluding buffer solution containing acetic acid and sodium acetate) or a diluted solution thereof, and having a pH of 3 to 6.
A method for dyeing a fiber material is provided, which comprises dyeing in a dye bath of No. 5.

【0006】本発明の方法においては、上記の各公報に
記載されているいずれのベンゾジフラノン化合物も分散
染料として使用することができるが、それらの中、特に
下記一般式(I)
In the method of the present invention, any of the benzodifuranone compounds described in the above publications can be used as the disperse dye. Among them, the following general formula (I) is particularly preferable.

【0007】[0007]

【化1】 [Chemical 1]

【0008】[式中Rは、水素原子、水酸基、C1 〜C
4 アルキル基、C1 〜C4 アルコキシC1 〜C4 アルキ
ル基、C1 〜C4 アルキルカルボニル基、C1 〜C4
ルコキシカルボニルC1 〜C4 アルキル基、フェニルC
1 〜C4 アルキル基、C1 〜C 4 アルコキシC1 〜C4
アルコキシカルボニルC1 〜C4 アルキル基、または−
OR1 Q(ここでR1 は、メチレン基、または水酸基、
1 〜C4 アルコキシ基、もしくはC1 〜C4 アルキル
カルボニルオキシ基で置換されていてもよい直鎖または
分岐のC2 〜C6 アルキレン基を表し、Qは置換されて
いてもよい5員または6員の飽和または不飽和の複素環
残基を表す。)を表わす。]で示される化合物の少なく
とも一種の使用が有利である。
[Wherein R is a hydrogen atom, a hydroxyl group, C1~ C
FourAlkyl group, C1~ CFourAlkoxy C1~ CFourArchi
Lu group, C1~ CFourAlkylcarbonyl group, C1~ CFourA
Lucoxycarbonyl C1~ CFourAlkyl group, phenyl C
1~ CFourAlkyl group, C1~ C FourAlkoxy C1~ CFour
Alkoxycarbonyl C1~ CFourAn alkyl group, or-
OR1Q (here R1Is a methylene group or a hydroxyl group,
C1~ CFourAlkoxy group or C1~ CFourAlkyl
A straight chain optionally substituted with a carbonyloxy group or
Branch C2~ C6Represents an alkylene group, where Q is substituted
5 or 6 membered saturated or unsaturated heterocycle which may be present
Represents a residue. ) Is represented. ] Fewer compounds
Both types are advantageous.

【0009】一般式(I)で示される化合物中、特に好
適に使用される化合物の具体例は下表1のとおりであ
る。
Among the compounds represented by the general formula (I), specific examples of the compounds which are particularly preferably used are shown in Table 1 below.

【0010】[0010]

【表1】 [Table 1]

【0011】これらの化合物は、アニオン系又はノニオ
ン系界面活性剤と共に水の存在下でサンドミル等によっ
て微粒化処理を施し、そのままで又は乾燥して粉状又は
顆粒状の分散染料として本発明を実施するために用いら
れる。
These compounds are subjected to atomization treatment with a sand mill or the like in the presence of water together with an anionic or nonionic surfactant, and as they are or dried, the present invention is carried out as a powdery or granular disperse dye. It is used to

【0012】本発明の方法はベンゾジフラノン系分散染
料を所定量の水中に分散懸濁させ、この懸濁液のpHを緩
衝作用によって3〜6.5に固定し、このようにして調
製した染浴に被染物である繊維材料を投入し、たとえ
ば、常圧下においてキャリアーの存在下で100 ℃までの
温度範囲で染色するか、あるいは密閉系染色装置内にお
いて加圧下で120 乃至150 ℃の温度範囲で染色すること
によって実施することができる。浴比は通常1:5乃至
1:50、そして染色時間は通常5乃至60分である。
According to the method of the present invention, a benzodifuranone-based disperse dye is dispersed and suspended in a predetermined amount of water, and the pH of the suspension is fixed to 3 to 6.5 by a buffering action. Then, the fiber material to be dyed is added to, and dyeing is carried out, for example, under normal pressure in the presence of a carrier at a temperature range of up to 100 ° C, or in a closed dyeing apparatus at a temperature range of 120-150 ° C under pressure. It can be carried out by dyeing. The bath ratio is usually 1: 5 to 1:50, and the dyeing time is usually 5 to 60 minutes.

【0013】pHが3〜6.5であるクラークラブズ
(Clark-Lubs) の緩衝溶液、シェーレンシェン(Sφrens
en) の緩衝溶液、コルソッフ(Kolthoff) の緩衝溶液、
ミハイル(Michaelis) の緩衝溶液、マックイベイン(Mc
Ivaine) の緩衝溶液、およびワルポール(Walpole) の緩
衝溶液は、いずれも「化学便覧基礎編II」、日本化学
会編、昭和41年9月25日丸善(株)発行に記載され
ているが、これらの緩衝溶液はそのまま、または、それ
らを適宜希釈して用いることができる。希釈率(当該緩
衝溶液の重量/水の重量)は特に制限されないが好まし
くは、1/2〜1/100の範囲である。本発明におけ
る染浴には、所望により湿潤剤、分散剤、泡防止剤など
通常、分散染料を用いる繊維材料の染色に用いられる染
色助剤を添加することができる。
Clark-Lubs buffer solution having a pH of 3 to 6.5, Sφrens
en) buffer solution, Kolthoff buffer solution,
Buffer solution of Michaelis, McIvein (Mc
The buffer solution of Ivaine) and the buffer solution of Walpole are both described in "Chemical Handbook Basic Edition II", edited by The Chemical Society of Japan, published by Maruzen Co., Ltd. on September 25, 1966. These buffer solutions can be used as they are, or can be used after diluting them appropriately. The dilution ratio (weight of the buffer solution / weight of water) is not particularly limited, but is preferably in the range of 1/2 to 1/100. If desired, a dyeing aid such as a wetting agent, a dispersant, an antifoaming agent or the like, which is usually used for dyeing a fiber material using a disperse dye, can be added to the dye bath in the present invention.

【0014】本発明における繊維材料としては、主とし
て芳香族ポリカルボン酸と多価アルコ−ルとの線上高分
子エステルからつくられた繊維材料、典型的にはテレフ
タル酸とエチレングリコ−ルまたはジメチルシクロヘキ
サンとからつくられたもの、およびテレフタル酸とイソ
フタル酸とエチレングリコ−ルとの共重合体からつくら
れたものであるポリエステル繊維材料が好ましい。これ
ら繊維材料の形状は任意であり、たとえば、フロック、
粗紡糸(スラッピング)、ヤ−ン、加工フィラメント、
編み物、織物などが例示される。本発明における繊維材
料としては、さらにポリアミド繊維材料、たとえばポリ
アミド6、ポリアミド66またはポリアミド12などを
挙げることができる。
As the fiber material in the present invention, a fiber material mainly made of linear polymer ester of aromatic polycarboxylic acid and polyhydric alcohol, typically terephthalic acid and ethylene glycol or dimethylcyclohexane. Polyester fiber materials made of terephthalic acid, isophthalic acid and ethylene glycol are preferred. The shape of these fibrous materials is arbitrary, for example, flock,
Roving (slapping), yarn, processed filament,
Knitting, woven fabric, etc. are exemplified. The fiber material in the present invention may further include polyamide fiber material such as polyamide 6, polyamide 66 or polyamide 12.

【0015】本発明の方法によれば、染色中のpH変化
がなく経済的かつ効果的な染色が可能であり、染色不良
による再染色処理が不必要であり、また、染色工程にお
ける分散染料の分解もなく、高い吸尽率をもって均染性
が優れ、色相変化のない、濃色の染色物を得ることがで
きる。
According to the method of the present invention, there is no change in pH during dyeing, economical and effective dyeing is possible, re-dyeing treatment due to poor dyeing is unnecessary, and disperse dyes in dyeing process are not required. It is possible to obtain a deep-colored dyeing product which is free from decomposition, has a high exhaustion rate, is excellent in levelness, and is free from hue change.

【0016】[0016]

【実施例】以下に本発明を実施例によって更に詳細に説
明するが、本発明はこれらの実施例によって制限される
ものではない。例中、部は重量部を表す。
EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples. In the examples, parts represent parts by weight.

【0017】実施例1 前記表1におけるNo.5の化合物1.0部をナフタレン
スルフォン酸とホルムアルデヒドの縮合物3.0部と共
に水性媒体中で微粒化分散した。この染料分散液を乾燥
して得られた粉末0.6 部を水で希釈して1000部とした。
更に、フタル酸水素カリウム8.9部および水酸化ナト
リウム0.954部を溶解させてpH5.0の緩衝溶液
とした。この染浴にテトロンジャージ(ポリエステル
布、東レ(株)製品)10部を浸し、加圧下130 〜135 ℃
で60分間染色を行った。次いで染色物を水酸化ナトリウ
ム3部、ハイドロサルファイト3部、ベタイン型両性界
面活性剤3部と水3,000 部からなる処理液で、85℃で10
分間還元洗浄を行い、水洗、乾燥したところ、均一で鮮
明な赤色の染色物が得られた。
Example 1 No. 1 in Table 1 above. 1.0 part of the compound of 5 was finely dispersed in an aqueous medium together with 3.0 parts of a condensate of naphthalene sulfonic acid and formaldehyde. 0.6 part of the powder obtained by drying this dye dispersion was diluted with water to 1000 parts.
Further, 8.9 parts of potassium hydrogen phthalate and 0.954 part of sodium hydroxide were dissolved to obtain a buffer solution having a pH of 5.0. Immerse 10 parts of Tetoron jersey (polyester cloth, product of Toray Industries, Inc.) in this dyebath and pressurize at 130-135 ° C.
Staining was performed for 60 minutes. Then, the dyed product was treated with a treatment solution containing 3 parts of sodium hydroxide, 3 parts of hydrosulfite, 3 parts of betaine-type amphoteric surfactant and 3,000 parts of water at 85 ° C.
After performing reduction washing for minutes, washing with water and drying, a uniform and bright red dyed product was obtained.

【0018】実施例2〜17 実施例1と同様に化合物(5)を用い染浴を作成した。
さらに、下表2に示す緩衝溶液にてpHを固定し、その後
も実施例1と同様に操作したところ、いずれの場合も、
均一で鮮明な赤色の染色物が得られた。
Examples 2 to 17 Dye baths were prepared in the same manner as in Example 1 using the compound (5).
Further, the pH was fixed with the buffer solution shown in Table 2 below, and the same operation as in Example 1 was carried out thereafter.
A uniform, bright red dyeing is obtained.

【0019】[0019]

【表2】 [Table 2]

【0020】実施例18〜34 化合物(5)の代りに前記表1における化合物No.1〜
4および6〜18を用い、実施例1と同様に染色を行
い、いずれの場合も、均一で鮮明な赤色の染色物を得
た。
Examples 18 to 34 Instead of the compound (5), the compound No. 1 to
Dyeing was performed in the same manner as in Example 1 using Nos. 4 and 6 to 18, and in each case, a uniform and clear red dyed product was obtained.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】ベンゾジフラノン系分散染料を用い、クラ
ークラブズ(Clark-Lubs) の緩衝溶液、シェーレンシェ
ン(Sφrensen) の緩衝溶液、コルソッフ(Kolthoff) の
緩衝溶液、ミハイル(Michaelis) の緩衝溶液(ただし、
酢酸および酢酸ソーダを含有する緩衝溶液を除く。) 、
マックイベイン(McIvaine)の緩衝溶液もしくはワルポー
ル(Walpole) の緩衝溶液(ただし、酢酸および酢酸ソー
ダを含有する緩衝溶液を除く。) またはそれらの希釈液
であって、pHが3〜6.5である染浴中で染色すること
を特徴とする繊維材料の染色方法。
1. A benzodifuranone-based disperse dye is used, and a Clark-Lubs buffer solution, a Sφrensen buffer solution, a Kolthoff buffer solution, and a Michaelis buffer solution (however,
The buffer solution containing acetic acid and sodium acetate is removed. ),
A McIvaine buffer solution or a Walpole buffer solution (excluding a buffer solution containing acetic acid and sodium acetate) or a diluted solution thereof, which has a pH of 3 to 6.5. A method for dyeing a fiber material, which comprises dyeing in a bath.
JP5150373A 1993-06-22 1993-06-22 Dyeing of fiber material with benzodifuranone-type disperse dye Pending JPH0711588A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5150373A JPH0711588A (en) 1993-06-22 1993-06-22 Dyeing of fiber material with benzodifuranone-type disperse dye

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5150373A JPH0711588A (en) 1993-06-22 1993-06-22 Dyeing of fiber material with benzodifuranone-type disperse dye

Publications (1)

Publication Number Publication Date
JPH0711588A true JPH0711588A (en) 1995-01-13

Family

ID=15495578

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5150373A Pending JPH0711588A (en) 1993-06-22 1993-06-22 Dyeing of fiber material with benzodifuranone-type disperse dye

Country Status (1)

Country Link
JP (1) JPH0711588A (en)

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