JPS58132181A - Dyeing of polyester fiber base material - Google Patents

Dyeing of polyester fiber base material

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Publication number
JPS58132181A
JPS58132181A JP57010230A JP1023082A JPS58132181A JP S58132181 A JPS58132181 A JP S58132181A JP 57010230 A JP57010230 A JP 57010230A JP 1023082 A JP1023082 A JP 1023082A JP S58132181 A JPS58132181 A JP S58132181A
Authority
JP
Japan
Prior art keywords
group
dye
formula
dyeing
light 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.)
Pending
Application number
JP57010230A
Other languages
Japanese (ja)
Inventor
国広 尚信
合田 勇
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.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals Inc
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 Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Priority to JP57010230A priority Critical patent/JPS58132181A/en
Publication of JPS58132181A publication Critical patent/JPS58132181A/en
Pending legal-status Critical Current

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Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 本発明はポリエステル繊維素材、特に自動車内装素材、
インチリヤ素材等、極めて高耐光堅ろう度が要求される
繊維製品の染色において特定のアンスラキノン糸赤色染
料に特定のアゾ系染料を配合して行うことにより橙色な
いし青赤色染色物の耐光堅ろう度を向上させる方法に関
するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention provides polyester fiber materials, particularly automobile interior materials,
When dyeing textile products that require extremely high light fastness, such as Inchiriya materials, the light fastness of orange or blue-red dyed products is improved by blending specific azo dyes with specific anthraquinone thread red dyes. This is related to how to do this.

従来、自動車内装素材には合成レザーが主体に使用され
ているが、高級化、ファッション化に伴ないカラフルな
繊維製品が広く利用されるようになって来た。
Traditionally, synthetic leather has been primarily used as an interior material for automobiles, but colorful textile products have come into widespread use as luxury and fashion have become more popular.

現在繊維素材としてはナイロンが主体であるが、ポリエ
ステル繊維が安価になりポリエステル繊維への指向が高
まっている。しかしこれら内装用繊紐製品に対する品質
要求はきびしく、各自動車メーカーは独自に品質規格を
定め特に耐光堅ろう度については極めてきびしくなって
いる。この耐光堅ろう度規格は各自動車メーカーによっ
て多少異なっているが、当初フェードメーター(ブラッ
クパイル温度63℃)で100時間照射後、変退色用グ
レースケールで判定3−4級というのが一般的であった
。しかしその後各自動車メーカーの自主規制強化から規
格は一層きびしくなり、真夏の炎天下、長時間放置の車
内の異常高温現象を考慮して、ブラックパネル温度が8
3℃となり、また実際ノシート成型時にはウレタンフオ
ームl[ちすることから、耐光堅ろう度測定時に10m
mのウレタンフオームを裏張りして測定するようになシ
照射時間も200時間以王が一般的となったっ特に中近
東など輸出向けは83℃で400時間照射して変退色グ
レースケールで3−4級以上が必要といわれている。又
従来より米国向は輸出車に行なわれてきた防炎加工が我
国でも車両火災の安全性に対する認識の高まりから実施
されるようになって来ている。一般に難燃加工にょシ耐
光堅ろう度が低下するため耐光向上剤を添加することに
より耐光堅ろう度を向上させる方法が取られるケースも
多いが、染料それ自体に従来よりさらに堅ろうなものが
要求されるようになって来ている。
Currently, nylon is the main fiber material, but as polyester fibers become cheaper, there is an increasing preference for polyester fibers. However, quality requirements for these interior cord products are strict, and each automobile manufacturer has established its own quality standards, which are particularly strict regarding light fastness. This light fastness standard differs slightly depending on each automobile manufacturer, but it was generally determined to be grade 3-4 on a gray scale for discoloration and fading after 100 hours of irradiation with a fade meter (black pile temperature 63 degrees Celsius). Ta. However, since then, the standards have become even stricter due to the strengthening of self-regulation by each automobile manufacturer, and the black panel temperature has been increased to 8.
3℃, and when actually molding the sheet, the urethane foam l[chi], so when measuring the light fastness,
The irradiation time is now more than 200 hours, and it has become common for measurements to be made using urethane foam as the lining.Especially for exports to the Middle East, etc., irradiation is performed at 83℃ for 400 hours, resulting in a discoloration and fading gray scale of 3-3. Level 4 or above is said to be required. Furthermore, the flame-retardant treatment that has traditionally been applied to cars exported to the United States is now being implemented in Japan as well, due to growing awareness of vehicle fire safety. Generally, light fastness decreases with flame retardant treatment, so in many cases a method is taken to improve light fastness by adding a light fastness improver, but the dye itself is required to be more robust than before. It's starting to look like this.

一般に赤色染料としてアンスラキノン系染料は耐光堅ろ
う度の点で優れておシ、通常の繊絣製品では十分な堅ろ
う度が得られる1、しかし自動車内装用の堅ろう度測定
法によりフェードメーターで200時間時間開射すると
アンスラキノン系赤色染料による染色物は通常青味側に
変色し堅ろう度の等級が低下する。特にスカーレットか
ら赤色の染色物においてはこの青味変色の傾向が強い。
In general, anthraquinone dyes have excellent light fastness as red dyes, and sufficient fastness can be obtained in ordinary textile kasted products.1 However, according to the fastness measurement method for automobile interiors, it has been tested for 200 hours using a fade meter. When exposed to light for a long time, dyed articles made with anthraquinone red dyes usually turn bluish and the fastness rating decreases. This bluish discoloration tends to be particularly strong in scarlet to red dyed products.

本発明者らは特定のアンスラキノン系赤色染料に特定の
アゾ系染料を配合することにより青味変色を防止し耐光
堅ろう度を向上させ得ることを見い出し本発明に至った
ものである。配合するアゾ系染料の耐光堅ろう度がアン
スラキノン系のそれよシも劣る場合においても配合染色
物の堅ろう度が両母体染料より向上することは驚くべき
ことである。
The present inventors have discovered that bluish discoloration can be prevented and light fastness can be improved by blending a specific azo dye with a specific anthraquinone red dye, leading to the present invention. It is surprising that even when the light fastness of the azo dye to be blended is inferior to that of the anthraquinone dye, the fastness of the blended dyed product is improved over both parent dyes.

従来から測色学的に見て、耐光堅ろう度の劣る染料を少
量配合すると染色物の耐光堅ろう度が予期以上に低下す
る例が多い。ただ耐光堅ろう度の非常に低い染料を配合
して逆に見掛は上堅ろう度が向上する例もあるといわれ
ているが、なお実用性(で乏しく分散染料ではその例を
見ない。本発明は極めて高耐光が得られ、しかもアンス
ラキノン系赤色染料よりも安価なアゾ染料を配合するの
であるため産業上の利用価値の大きい発明である。
From a colorimetric perspective, there have been many cases in which the light fastness of a dyed product decreases more than expected when a small amount of a dye with poor light fastness is added. However, it is said that there are cases in which the apparent fastness is improved by blending dyes with very low light fastness, but this is not practical and there are no examples of this with disperse dyes.The present invention This invention has great industrial value because it provides extremely high light resistance and contains an azo dye that is cheaper than anthraquinone red dyes.

本来耐光堅ろう度には化学構造に起因する要素が極めて
大きいが物理的な要素もあり、文献(新染色加工講座4
)によると染着状態における光退色は染料と繊維、染料
と染料または助剤との相互作用が影響するといわれてい
る。一般に染料の会合により多かれ少なかれ光の吸収ス
ペクトルが変化する。会合体内における分子の並び方に
より、スペクトルの位置、強度の変化は異なるが一般に
光の吸収は減少し、大きな集合体が生成すれば集合体内
に包みこまれた染料分子は直接光に当ることはないので
光吸収のため有効濃度が減少し、光の吸収はおちるもの
と考えら′れている。
Originally, light fastness has a very large element due to chemical structure, but there are also physical factors.
), photobleaching in the dyed state is said to be affected by the interaction between the dye and the fiber, and the interaction between the dye and the dye or auxiliary agent. Generally, the association of dyes changes the light absorption spectrum to a greater or lesser extent. Changes in spectral position and intensity vary depending on the arrangement of molecules within the aggregate, but in general light absorption decreases, and if a large aggregate is formed, the dye molecules wrapped within the aggregate will not be directly exposed to light. Therefore, it is thought that the effective concentration decreases due to light absorption, and light absorption stops.

本発明における場合は測色学的に変色が見掛は上打ち消
し合うこと、および配合における染料の集杏度変化、両
染料の拡散度合が異なるなどの要素が複雑にかさなって
耐光堅ろう度が向上したものであると推定される。
In the case of the present invention, light fastness is improved due to a complex combination of factors such as the colorimetric changes that appear to cancel each other out, changes in the concentration of dyes in the formulation, and differences in the degree of diffusion of both dyes. It is presumed that the

なお本発明において染色の際に第3成分として耐光堅ろ
う度の優れた黄色染料等を添加しても効果は特に変わら
ず、配合使用が可能である。
In addition, in the present invention, even if a yellow dye with excellent light fastness is added as a third component during dyeing, the effect will not change in particular, and it can be used in combination.

次に実施例により本発明の方法を具体的に説明する。な
お実施例中の部は重量部を表わす。
Next, the method of the present invention will be specifically explained using Examples. Note that parts in the examples represent parts by weight.

実施例1 下記の式■で示すアンスラキノン系赤色染料4.5部(
染料原体30%とアニオン活性剤70%からなる混合物
を微粒化乾燥して調製)および式嘔で示すアゾ系染料1
.5部(染料原体30%とアニオン活性剤70%からな
る混合物を微粒化、乾燥して調製)を含有する1000
部の染料分散液にポリエステル織物100部を入れ13
0℃で60分間高温染色し通常の如く還元洗浄し乾燥す
る。
Example 1 4.5 parts of anthraquinone red dye represented by the following formula (
Prepared by atomizing and drying a mixture consisting of 30% dyestuff and 70% anionic activator) and azo dye 1 shown in the formula
.. 1000 containing 5 parts (prepared by atomizing and drying a mixture consisting of 30% dyestuff and 70% anionic activator)
Add 100 parts of polyester fabric to 13 parts of dye dispersion.
High temperature dyeing is carried out at 0° C. for 60 minutes, followed by reduction washing and drying as usual.

本染色物をフェードメーター(ブラックパイル温度83
℃、ウレタンフオーム裏打チ)で200時間照射し変退
色用グレースケールで判定すると4級であり退色部の青
変は非常に小さかった。−方、式未の染料6部を単独使
用して染色した染色物の耐光堅ろう度は変退色用グレー
スケールで3−4級であり、退色部は相当青変していた
Measure the actual dyeing using a fade meter (black pile temperature 83).
℃, urethane foam lining for 200 hours, and judged on the gray scale for discoloration and fading, it was grade 4, and the blue discoloration in the discolored area was very small. - The light fastness of the dyed product dyed using 6 parts of the unconventional dye alone was grade 3-4 on the gray scale for discoloration and fading, and the fading areas were considerably blued.

実施例2 実施例1において式■の染料に代えて弐Vの染料(染料
原体30%とアニオン活性剤70%からなる混合物を微
粒化、乾燥して調製)1.5部を用いたほかは実施例1
に記載したと全く同様に実施した。
Example 2 In Example 1, 1.5 parts of the dye of formula 2 (prepared by atomizing and drying a mixture consisting of 30% dyestuff and 70% anionic activator) was used instead of the dye of formula (1). is Example 1
It was carried out in exactly the same manner as described.

得られた染色物の耐光堅ろう度は変退色用グレースケー
ルで4級であり、退色部の青変は非常に小さかった。
The light fastness of the obtained dyed product was grade 4 on the gray scale for discoloration and fading, and the blue discoloration in the fading areas was very small.

実施例3 実施例1において式■の染料に代えて式■の染料(染料
原体30%とアニオン活性剤70%からえたほかは実施
例1に記載したと同様に実施した。
Example 3 The same procedure as described in Example 1 was carried out, except that the dye of formula (1) was replaced with the dye of formula (1) (30% dyestuff and 70% anionic activator).

得られた染色物の耐光堅ろう度は変退色グレースケール
で4級であり、退色部の青変は少なかった 実施例4 実施例1において式■の染料に代えて式■の染料(染料
原体25%とアニオン活性剤75%からなる混合物を微
粒化乾燥して調製)5部、式■の染料に代えて式■の染
料(染料原体30%とアニオン活性剤70%からなる混
合物を微粒化乾燥して調製)2部を加えたほかは実施例
1に記載したと同様に実施した。
The light fastness of the obtained dyed product was grade 4 on the fading gray scale, and there was little blue discoloration in the fading area.Example 4 In Example 1, the dye of formula 5 parts of the dye of formula (prepared by atomizing and drying a mixture consisting of 25% of the dyestuff and 75% of the anionic activator), 5 parts of the dye of the formula The procedure was carried out in the same manner as described in Example 1, except that 2 parts (prepared by drying) were added.

得られた染色物の耐光堅らう度は変退色グレースケール
で4級であり、退色部の青変は殆んど認められなかった
The light fastness of the obtained dyed product was grade 4 on the fading gray scale, and almost no blue discoloration was observed in the fading areas.

染料1.5部と共にミケトンポリエステルイエローGS
L(三井東圧化学社製、C−■・ディスバーズ イエロ
ー149)1.5部を加えたほかは実施例1に記載した
と同様に染色した。
Miketone Polyester Yellow GS with 1.5 parts dye
Dyeing was carried out in the same manner as described in Example 1, except that 1.5 parts of L (manufactured by Mitsui Toatsu Chemical Co., Ltd., C-■・Disverse Yellow 149) was added.

得られた染色物をフェードメーター(ブラックパネル温
度83℃、ウレタンフオーム裏打ち)で200時間照射
し変退色グレースケールで判定すると3−4級であり退
色部の青変は非常に小さかった。
The obtained dyed product was irradiated for 200 hours using a fade meter (black panel temperature: 83° C., urethane foam lining), and when judged on the fading gray scale, it was grade 3-4, and the blue discoloration in the faded areas was very small.

一方式量の染料6部とミケトンポリエステルイエローG
SL1.5 部を使用して染色した染色物の耐光堅ろう
度は変退色用グレースケールで3級であり退色部は相当
青変していた 特許出願人 三井東圧化学株式会社
One formula amount of 6 parts of dye and Miketone Polyester Yellow G
The light fastness of dyed products dyed using SL1.5 parts was grade 3 on the gray scale for discoloration and fading, and the fading areas were considerably blued. Patent applicant Mitsui Toatsu Chemical Co., Ltd.

Claims (2)

【特許請求の範囲】[Claims] (1)式I (式中、R1は置換基を有し得るアルキル基又はフェニ
ル基を表わす)なるアンスラキノン系赤色染料に、式■ (式中、2はニトロ基、シアノ基又はアルコキシカルボ
ニル基を% XI、 X2は同−又は異なってもよく水
素、シアノ基、ハロゲノ基又はアルキ:17 シ基ヲ、
 Ylは水素、アルキルベンソイルアミン基、アルキル
アミド基又はハロゲノ基を、Y!は水素又はアルコキシ
基を、R2、Rsは同−又は異なっていてもよい水素、
アルキル基1シアノエチル基、シアノアルコキシアルキ
ル基、アルコキシアルキル基、アルキルカルボニルオキ
シアルキル基、ベンジル基、フェノキシエチル基、アリ
ル基、置換基を有し得るベンゾイルオキシアルキル基、
アルコキシカルボニルオキシアルキル基、アルコキシカ
ルボニルアルキル基又はクロルプロピオニルオキシエチ
ル基ヲ表わす)である橙色、黄褐色、赤色ないし青赤色
のアゾ染料を配合して行うことを特徴とするポリエステ
ル繊維素材の染色方法。
(1) An anthraquinone red dye of formula I (wherein R1 represents an alkyl group or phenyl group that may have a substituent) is added to an anthraquinone red dye of formula II (wherein 2 is a nitro group, a cyano group, or an alkoxycarbonyl group). %XI, X2 may be the same or different, hydrogen, cyano group, halogeno group or alkyl group: 17
Yl represents hydrogen, an alkylbenzoylamine group, an alkylamide group, or a halogeno group, and Y! represents hydrogen or an alkoxy group, R2 and Rs may be the same or different,
Alkyl group 1 cyanoethyl group, cyanoalkoxyalkyl group, alkoxyalkyl group, alkylcarbonyloxyalkyl group, benzyl group, phenoxyethyl group, allyl group, benzoyloxyalkyl group that may have a substituent,
A method for dyeing a polyester fiber material, characterized in that it is carried out by blending an orange, tan, red or blue-red azo dye which is an alkoxycarbonyloxyalkyl group, an alkoxycarbonyloxyalkyl group or a chloropropionyloxyethyl group.
(2)式Iの染料が1−アミノ−2−(6−ヒトロキシ
ヘキシルオキシ)−4−ヒドロキシアンスラキノンであ
ることを特徴とする特許請求の範囲第1項記載の方法。
2. Process according to claim 1, characterized in that the dye of formula I is 1-amino-2-(6-hydroxyhexyloxy)-4-hydroxyanthraquinone.
JP57010230A 1982-01-27 1982-01-27 Dyeing of polyester fiber base material Pending JPS58132181A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57010230A JPS58132181A (en) 1982-01-27 1982-01-27 Dyeing of polyester fiber base material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57010230A JPS58132181A (en) 1982-01-27 1982-01-27 Dyeing of polyester fiber base material

Publications (1)

Publication Number Publication Date
JPS58132181A true JPS58132181A (en) 1983-08-06

Family

ID=11744479

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57010230A Pending JPS58132181A (en) 1982-01-27 1982-01-27 Dyeing of polyester fiber base material

Country Status (1)

Country Link
JP (1) JPS58132181A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0305887A2 (en) * 1987-09-02 1989-03-08 Hoechst Aktiengesellschaft Dye mixtures for producing fast blue and navy blue dyeings on mixed materials of polyester and cellulose fibres
JP2004077707A (en) * 2002-08-14 2004-03-11 Ricoh Co Ltd Electrostatic charge image developing toner and image forming method
CN1312227C (en) * 2004-12-16 2007-04-25 浙江龙盛集团股份有限公司 Dispersed blue dye composition
CN113462190A (en) * 2021-06-30 2021-10-01 嘉禾宜事达(沈阳)化学有限公司 Azo dye compound with high washing fastness, preparation method and application

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0305887A2 (en) * 1987-09-02 1989-03-08 Hoechst Aktiengesellschaft Dye mixtures for producing fast blue and navy blue dyeings on mixed materials of polyester and cellulose fibres
EP0305887A3 (en) * 1987-09-02 1991-06-12 Hoechst Aktiengesellschaft Dye mixtures for producing fast blue and navy blue dyeings on mixed materials of polyester and cellulose fibres
JP2004077707A (en) * 2002-08-14 2004-03-11 Ricoh Co Ltd Electrostatic charge image developing toner and image forming method
CN1312227C (en) * 2004-12-16 2007-04-25 浙江龙盛集团股份有限公司 Dispersed blue dye composition
CN113462190A (en) * 2021-06-30 2021-10-01 嘉禾宜事达(沈阳)化学有限公司 Azo dye compound with high washing fastness, preparation method and application

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