JPH068387B2 - Monoazo compound and dyeing method for hydrophobic fiber using the same - Google Patents
Monoazo compound and dyeing method for hydrophobic fiber using the sameInfo
- Publication number
- JPH068387B2 JPH068387B2 JP61279841A JP27984186A JPH068387B2 JP H068387 B2 JPH068387 B2 JP H068387B2 JP 61279841 A JP61279841 A JP 61279841A JP 27984186 A JP27984186 A JP 27984186A JP H068387 B2 JPH068387 B2 JP H068387B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- formula
- dyeing
- monoazo compound
- hydrophobic fiber
- 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
- 238000004043 dyeing Methods 0.000 title claims description 17
- -1 Monoazo compound Chemical class 0.000 title claims description 12
- 239000000835 fiber Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 230000002209 hydrophobic effect Effects 0.000 title claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000004744 fabric Substances 0.000 description 9
- 239000000986 disperse dye Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- MUERWWKQVXXPML-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 MUERWWKQVXXPML-UHFFFAOYSA-N 0.000 description 1
- KYAXCYQVBBQQHB-UHFFFAOYSA-N 3-methyl-2-phenyl-1h-indole Chemical compound N1C2=CC=CC=C2C(C)=C1C1=CC=CC=C1 KYAXCYQVBBQQHB-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はモノアゾ化合物及びこれを用いる疎水性繊維の
染色法に関する。TECHNICAL FIELD The present invention relates to a monoazo compound and a method for dyeing a hydrophobic fiber using the same.
従来の技術 繊維材料を衣料用以外の分野に応用することは従来から
よく行なわれていたが、近年、染色加工業の加工分野の
拡大、製品の差別化、消費者の高級感指向から、その応
用範囲が急速に拡がってきている。その一つとしてポリ
エステル繊維材料の自動車内装材及びインテリア材料と
しての用途開発が挙げられる。BACKGROUND ART Conventionally, it has been well practiced to apply fiber materials to fields other than clothing, but in recent years, due to the expansion of the processing field of the dyeing processing industry, product differentiation, and consumers' sense of luxury, The range of applications is expanding rapidly. One of these is the development of applications of polyester fiber materials as automobile interior materials and interior materials.
これらの用途においては、日光に晒されることが多く、
耐光堅牢度の優れたものが要求されることが多い。特に
自動車は、利用地域、季節等の条件によっては、車内温
度が相当高くなるため、内装材料（染色物）に対する品
質特性特に耐光性、耐熱性については、厳しい品質が求
められている。ポリエステル繊維は、その耐熱性、耐光
性が良いことと、風合等ファション性が良いことで、自
動車内装材として広く利用されるようになってきたが、
それに伴って、着色材料である分散染料に対しても、一
段と優れた堅牢度、特に高い温度での優れた耐光堅牢度
が求められるようになってきた。例えば通常の染色布の
耐光堅牢度はJIS-L0842に規定する方法によって、温度
６３±３℃でカーボンアーク燈等を露光することによっ
て測定されているが、自動車内装用途では８３±３℃と
いうような高温下でしかも３００時間又はそれ以上の時
間露光するという厳しい条件のもとでの試験が行なわ
れ、それに耐えるだけの堅牢度をもった染料はそれ程多
くない。In these applications, they are often exposed to sunlight,
It is often required to have excellent light fastness. Particularly in automobiles, the temperature inside the vehicle is considerably high depending on the conditions such as the area of use and the season. Therefore, strict quality is required in terms of quality characteristics, especially light resistance and heat resistance, with respect to interior materials (dyes). Polyester fiber has been widely used as an automobile interior material because of its good heat resistance, light resistance, and good fashionability such as feeling.
Along with this, the disperse dyes, which are coloring materials, are required to have much higher fastness, particularly, fastness to light at high temperature. For example, the light fastness of ordinary dyed fabrics is measured by exposing a carbon arc lamp or the like at a temperature of 63 ± 3 ° C according to the method specified in JIS-L0842, but is 83 ± 3 ° C for automotive interior applications. Tests have been conducted under severe conditions of exposure at extremely high temperatures and for 300 hours or more, and there are not so many dyes having fastnesses that can withstand the exposure.
一般的に、分散染料の中で、耐光堅牢度の比較的良いも
のはアンスラキノン系の染料であるかそれらは概して着
色力に劣るのが欠点である。又、着色力の優れるアゾ系
分散染料は一般的には耐光堅牢度が劣るという傾向があ
る。殊に前記したような自動車用内装材としては濃度の
染色物が要求されることが多いので着色力に優れたアゾ
染料で耐光堅牢度の優れた分散染料の開発が強く望まれ
ている。In general, among disperse dyes, those having relatively good light fastness are anthraquinone type dyes, or they are generally inferior in tinting strength. Further, azo disperse dyes having excellent tinting strength generally tend to have poor light fastness. In particular, as the above-mentioned interior materials for automobiles, a dyed product having a high concentration is often required, and therefore, development of a disperse dye which is an azo dye having an excellent coloring power and an excellent light fastness is strongly desired.
黄色のアゾ系分散染料としては、C.I.Disperse Yellow
163、C.I.Disperse Orange 30が比較的優れた耐光堅牢度
を有するが、自動車用内装材としての前記したような厳
しい要求には、まだ不十分であり、更に強い耐光堅牢度
を有する分散染料が求められている。As a yellow azo disperse dye, CI Disperse Yellow
163, CIDisperse Orange 30 has relatively excellent light fastness, but it is still insufficient for the above-mentioned strict requirements as interior materials for automobiles, and a disperse dye having stronger light fastness is required. ing.
発明が解決しようとする問題点 自動車内装材及び特殊インテリア用等の素材として十分
利用出来る程度に、高温における耐光堅牢度の優れたア
ゾ系黄色分散染料の開発が望まれている。Problems to be Solved by the Invention Development of an azo yellow disperse dye having excellent fastness to light at high temperatures is desired so that it can be sufficiently used as a material for automobile interior materials and special interior materials.
問題点を解決するための手段 本発明者らは、前記したような問題点を解決すべく鋭意
努力した結果、式(I) （式(I)中、X1，X2は水素原子、塩素原子又は臭素原子
を表す（但し、X1とX2は同時には水素原子を表さな
い）。Ｒは低級アルキル基又はアリル基を表す） で表されるモノアゾ化合物が耐光堅牢度において特に優
れることを見いだし、本発明を完成させた。Means for Solving the Problems The present inventors have made diligent efforts to solve the problems as described above, and as a result, the formula (I) (In the formula (I), X 1 and X 2 represent a hydrogen atom, a chlorine atom or a bromine atom (provided that X 1 and X 2 do not represent a hydrogen atom at the same time). R represents a lower alkyl group or an allyl group. The present invention has been completed by finding that the monoazo compound represented by the formula (4) is particularly excellent in light fastness.
前記式(I)で示される化合物は例えば式(II) （式(II)中、X1，X2は水素原子、塩素原子又は臭素原子
を表す） で示される化合物を公知の方法でジアゾ化し、式(III) （Ｒは低級アルキル基又はアリル基を表す） で示されるインドール誘導体とカップリングすることに
より得られる。The compound represented by the formula (I) is, for example, the compound represented by the formula (II) (In the formula (II), X 1 and X 2 represent a hydrogen atom, a chlorine atom or a bromine atom), and the compound represented by the formula (III) is diazotized by a known method. (R represents a lower alkyl group or an allyl group) and is obtained by coupling with an indole derivative.
本発明の式(I)のアゾ化合物は疎水性繊維例えばポリエ
チレンテレフタレート、ポリエチレンテレフタレートを
主体とするポリエステル、セルロースジアセテート、セ
ルローストリアセテート等よりなる繊維類あるいはこれ
ら同志又はこれらとポリアクリロニトリル繊維、セルロ
ース繊維等他繊維との混紡繊維類の染色・捺染に適す
る。The azo compound of the formula (I) of the present invention is a hydrophobic fiber such as polyethylene terephthalate, polyester mainly composed of polyethylene terephthalate, fibers composed of cellulose diacetate, cellulose triacetate, etc. Suitable for dyeing and printing mixed fibers with other fibers.
前記したような疎水性繊維の染色は常法により行われる
が例えばポリエステル繊維の染色はそれ自体公知の方法
により例えば次のような方法によって染色される。The above-mentioned dyeing of the hydrophobic fiber is carried out by a conventional method, but the dyeing of the polyester fiber is carried out by a method known per se, for example, by the following method.
(I)浸染法 水媒体中で加圧下１２０〜１４０℃、３０〜９０分染色
を行う。(I) Dyeing method Dyeing is performed in an aqueous medium under pressure at 120 to 140 ° C. for 30 to 90 minutes.
(II)キャリアー法 メチルナフタレン、モノクロルベンゼン等のキャリアー
の存在下で水媒体中９０〜１００℃で染色を行う。(II) Carrier Method Dyeing is carried out in an aqueous medium at 90 to 100 ° C. in the presence of a carrier such as methylnaphthalene or monochlorobenzene.
(III)サーモゾル法 本発明の化合物を粉砕してえた粉砕染料を含む液に布を
パッティングし次いで中間乾燥し引き続き１８０〜２１
０℃で乾熱処理を施す。(III) Thermosol method The cloth is put on a liquid containing a crushed dye obtained by crushing the compound of the present invention, followed by intermediate drying and then 180 to 21.
A dry heat treatment is performed at 0 ° C.
以上の染色において、耐光性を更に向上する為に、紫外
線吸収剤を併用してもよい。染料によっては、紫外線吸
収剤との相性が悪く、紫外線吸収材の添加により逆に耐
光堅牢度が低下するものがあるが、本発明の式(I)化合
物はそのような現象を起こさず耐光堅牢度が著しく向上
する。In the above dyeing, an ultraviolet absorber may be used in combination in order to further improve the light resistance. Some dyes have poor compatibility with ultraviolet absorbers, but the addition of ultraviolet absorbers reduces the light fastness on the contrary, but the compound of formula (I) of the present invention does not cause such a phenomenon and is light fast. The degree is significantly improved.
なお本発明の化合物はそれらを２種以上混合して用いて
もよいし又染色のあと帯電防止加工等通常の後加工処理
を施してもよい。更に本発明の化合物と他の染料との混
合物を用いても、本発明の化合物の特性がそこなわれる
ことはない。The compounds of the present invention may be used as a mixture of two or more thereof, or may be subjected to usual post-treatment such as antistatic treatment after dyeing. Furthermore, the use of mixtures of the compounds of the invention with other dyes does not compromise the properties of the compounds of the invention.
又、本発明の化合物は、アルカリに対する耐性が強く、
アルカリ側での染色にも十分耐え得る特性を有し、染色
物の耐摩擦堅牢度も優れている。Further, the compound of the present invention has strong resistance to alkali,
It has the property that it can withstand dyeing even on the alkaline side, and has excellent abrasion resistance in dyeing.
実施例 本発明を実施例によって更に詳細に説明する。尚実施例
中、部及び％は重量部及び重量％を示すものとする。EXAMPLES The present invention will be described in more detail by way of examples. In addition, in an Example, a part and% shall show a weight part and weight%.
実施例１ 2,6−ジクロル−４−ニトロアニリン１0.３５部を濃硫
酸１７部に溶解せしめ、その液に、４３％ニトロシル硫
酸１5.２４部を徐々に加えた後、４０〜４５℃に３時間
保つことによりジアゾ化を完結させた。そのジアゾ液
を、別途調製した、３０％硫酸２００部、スルファミン
酸0.１部、Tween80（ノニオン系界面活性剤、純正化学
（株）製）0.５部、氷１２０部よりなる液に滴下した。
得られたジアゾ液に別途調製した、濃硫酸１０３部とＮ
−メチル−２−フェニルインドール１0.４部よりなるカ
ップラー液を温度が５℃以上にならないよう氷を加えな
がら徐々に滴下し、その後０−５℃に５時間保った。次
いで反応液を７０℃に昇温し、同温度で１時間攪拌した
後、生成物を別し、水洗、乾燥して下記式で示される
モノアゾ化合物１8.９部を得た。Example 1 10.35 parts of 2,6-dichloro-4-nitroaniline was dissolved in 17 parts of concentrated sulfuric acid, and 15.24 parts of 43% nitrosyl sulfuric acid was gradually added to the solution, and then the mixture was heated to 40 to 45 ° C. The diazotization was completed by keeping it for 3 hours. The diazo solution was added dropwise to a separately prepared solution consisting of 200 parts of 30% sulfuric acid, 0.1 part of sulfamic acid, 0.5 part of Tween80 (nonionic surfactant, manufactured by Junsei Chemical Co., Ltd.), and 120 parts of ice. did.
The diazo solution thus obtained was separately prepared, and 103 parts of concentrated sulfuric acid and N were added.
A coupler solution consisting of 10.4 parts of methyl-2-phenylindole was gradually added dropwise while adding ice so that the temperature did not rise above 5 ° C, and then kept at 0-5 ° C for 5 hours. Next, the reaction solution was heated to 70 ° C. and stirred at the same temperature for 1 hour, then the product was separated, washed with water and dried to obtain 18.9 parts of a monoazo compound represented by the following formula.
λmax（アセトン中）は４００nmであった。 λmax (in acetone) was 400 nm.
実施例２〜８ 実施例１と同様の方法で、ジアゾ成分とカップリング成
分を変えることにより下記化合物が得られた。Examples 2 to 8 The following compounds were obtained by changing the diazo component and the coupling component in the same manner as in Example 1.
実施例９〜１１ 実施例９と同様の方法で、ジアゾ成分とカップリング成
分を変えることにより、下記化合物が得られた。 Examples 9 to 11 The following compounds were obtained by changing the diazo component and the coupling component in the same manner as in Example 9.
実施例１２ (A)微粒子化染料の調製 実施例１でえられたモノアゾ
化合物１５部、デモールＮ２０部（花王アトラス製、分
散剤）、デモールＣ１５部（花王アトラス社製、分散
剤）及び水８０部を混合しサウンドグラインダーを用い
て最大径５μ以下になる迄微粒子化し、乾燥することに
より微粒子化染料粉末を得た。 Example 12 (A) Preparation of microparticulate dye 15 parts of the monoazo compound obtained in Example 1, 20 parts of demole N (manufactured by Kao Atlas, dispersant), 15 parts of demole C (manufactured by Kao Atlas, dispersant) and water 80 Part of the mixture was mixed into fine particles using a sound grinder until the maximum diameter became 5 μm or less, and dried to obtain fine particle dye powder.
(B)染色 前記で得た微粒子化染料0.１部を、水１５０
部に分散せしめ、酢酸と酢酸ソーダでpH4.５に調製した
後、ポリエステル繊維製布５部を加え加圧下１３０℃で
６０分染色後、取り出し水洗した。(B) Dyeing 0.1 part of the finely divided dye obtained above is mixed with 150 parts of water.
The mixture was dispersed in 1 part and adjusted to pH 4.5 with acetic acid and sodium acetate, 5 parts of polyester fiber cloth was added, dyed at 130 ° C. for 60 minutes under pressure, taken out and washed with water.
次いで、水１０００部中に苛性ソーダ２部、ハイドロサ
ルファイト２部、サンモールＲＣ７００（日華化学社
製、還元洗浄助剤）１部を溶解した液３０００部を用い
て、８０℃で１０分間還元洗浄を行い、水洗、乾燥し
た。黄色の染色布が得られた。Next, using 3000 parts of a solution prepared by dissolving 2 parts of caustic soda, 2 parts of hydrosulfite, and 1 part of Sunmor RC700 (reducing cleaning aid by Nikaka Chemical Co., Ltd.) in 1000 parts of water, reduction was carried out at 80 ° C. for 10 minutes. It was washed, washed with water and dried. A yellow dyed fabric is obtained.
(C)後加工処理 (B)で得られた染布を水１００部にナイ
スボールＦＬ（日華化学社製、帯電防止剤）１部を溶解
した液に浸漬し、均一に絞った後、１００℃で３分間中
間乾燥をし、更に１５０℃で３分間キュアリングをする
ことにより、帯電防止加工を行った。加工前後の変色は
なく、水、洗濯堅牢度等の低下もみられなかった。(C) Post-processing treatment The dyed cloth obtained in (B) is dipped in a solution in which 100 parts of water is dissolved in 1 part of Nice Ball FL (an antistatic agent manufactured by Nichika Chemical Co., Ltd.) and squeezed evenly. Antistatic processing was performed by intermediate drying at 100 ° C. for 3 minutes and curing at 150 ° C. for 3 minutes. There was no discoloration before and after processing, and no deterioration in water, washing fastness, etc. was observed.
又帯電防止を施す前後の染色布につき８３℃で３００時
間カーボンアーク燈による照射試験を実施したがほとん
ど褪色が認められなかった。Further, the dyed cloth before and after antistatic treatment was subjected to a carbon arc lamp irradiation test at 83 ° C. for 300 hours, but almost no fading was observed.
実施例１３ (A)微粒子化染料の調製 実施例６でえられたモノアゾ
化合物１５部、デモールＮ２０部、デモールＣ１５部及
び水８０部を混合しサウンドグラインダーを用いて最大
径５μ以下になる迄微粒子化し、乾燥することにより微
粒子化染料粉末を得た。Example 13 (A) Preparation of microparticulate dye 15 parts of the monoazo compound obtained in Example 6, 20 parts of demol N, 15 parts of demol C and 80 parts of water are mixed and fine particles are mixed with a sound grinder until the maximum diameter becomes 5 μm or less. It was pulverized and dried to obtain a finely divided dye powder.
(B)染色 前記で得た微粒子化染料0.１部とCibatex LF
（紫外線吸収剤、チバガイギー社製）0.１部を、水１５
０部に分散せしめ、酢酸と酢酸ソーダでpHを4.５に調整
した後、ポリエステル繊維製布５部を加え加圧下１３０
℃で６０分染色後、取り出し水洗した。(B) Dyeing 0.1 part of the finely divided dye obtained above and Cibatex LF
(UV absorber, manufactured by Ciba Geigy) 0.1 part is added to water 15
Disperse it in 0 parts, adjust the pH to 4.5 with acetic acid and sodium acetate, then add 5 parts of polyester fiber cloth and pressurize it to 130
After dyeing at 60 ° C. for 60 minutes, it was taken out and washed with water.
次いで、水１０００部中に苛性ソーダ２部、ハイドロサ
ルファイト２部、サンモールＲＣ７００１部を溶解した
液３０００部を用いて、８０℃で１０分間還元洗浄を行
い、水洗、乾燥した。黄色の染色布が得られた。Next, using 3000 parts of a liquid obtained by dissolving 2 parts of caustic soda, 2 parts of hydrosulfite, and 7001 parts of Sanmor RC700 in 1000 parts of water, reduction washing was performed at 80 ° C. for 10 minutes, washing with water and drying. A yellow dyed fabric is obtained.
この染布につき８３℃で３００時間のカーボンアーク燈
照射試験を実施したがほとんど褪色が認められなかっ
た。This dyed cloth was subjected to a carbon arc lamp irradiation test at 83 ° C. for 300 hours, but almost no fading was observed.
発明の効果 高温における耐光堅牢度の優れたアゾ系の黄色染料が得
られた。Effects of the Invention An azo yellow dye having excellent fastness to light at high temperature was obtained.
Claims (2)
子を表す。（但しX1とX2は同時には水素原子を表さな
い）Ｒは低級アルキル基又はアリル基を表す。） で表されるモノアゾ化合物1. A formula (I) (In the formula (I), X 1 and X 2 represent a hydrogen atom, a chlorine atom or a bromine atom. (However, X 1 and X 2 do not represent a hydrogen atom at the same time) R represents a lower alkyl group or an allyl group. The monoazo compound represented by
子を表す。（但しX1とX2は同時には水素原子を表さな
い）Ｒは低級アルキル基又はアリル基を表す。） で表されるモノアゾ化合物を用いることを特徴とする疎
水性繊維の染色法。2. Formula (I) (In the formula (I), X 1 and X 2 represent a hydrogen atom, a chlorine atom or a bromine atom. (However, X 1 and X 2 do not represent a hydrogen atom at the same time) R represents a lower alkyl group or an allyl group. A dyeing method for a hydrophobic fiber, which comprises using a monoazo compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61279841A JPH068387B2 (en) | 1986-11-26 | 1986-11-26 | Monoazo compound and dyeing method for hydrophobic fiber using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61279841A JPH068387B2 (en) | 1986-11-26 | 1986-11-26 | Monoazo compound and dyeing method for hydrophobic fiber using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63135455A JPS63135455A (en) | 1988-06-07 |
| JPH068387B2 true JPH068387B2 (en) | 1994-02-02 |
Family
ID=17616674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61279841A Expired - Lifetime JPH068387B2 (en) | 1986-11-26 | 1986-11-26 | Monoazo compound and dyeing method for hydrophobic fiber using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH068387B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4422293A1 (en) | 1994-06-25 | 1996-01-04 | Cassella Ag | Monoazoindole dyes |
| CN102604414B (en) * | 2012-01-16 | 2013-12-04 | 杭州吉华江东化工有限公司 | Azo compound containing phenylindole, preparation method and application thereof |
| TWI887021B (en) * | 2020-03-17 | 2025-06-11 | 日商紀和化學工業股份有限公司 | Dye composition |
| TWI810535B (en) * | 2020-03-17 | 2023-08-01 | 國立大學法人福井大學 | Dyes for dyeing with supercritical carbon dioxide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5515747B2 (en) * | 1971-08-12 | 1980-04-25 |
-
1986
- 1986-11-26 JP JP61279841A patent/JPH068387B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Ｊ、Ｃｈｅｍ、Ｓｏｃ、，ＰｅｒｋｉｎＴｒａｎｓ２（４）Ｐ．６２８−３２ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63135455A (en) | 1988-06-07 |
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