JP2006514126A - Yellow disperse dye mixture with high light fastness - Google Patents
Yellow disperse dye mixture with high light fastness Download PDFInfo
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- JP2006514126A JP2006514126A JP2004530073A JP2004530073A JP2006514126A JP 2006514126 A JP2006514126 A JP 2006514126A JP 2004530073 A JP2004530073 A JP 2004530073A JP 2004530073 A JP2004530073 A JP 2004530073A JP 2006514126 A JP2006514126 A JP 2006514126A
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- 0 CO*(C=C1)C=Cc(nc2-c3cccc4cccc5c34)c1[n]2C5=O Chemical compound CO*(C=C1)C=Cc(nc2-c3cccc4cccc5c34)c1[n]2C5=O 0.000 description 1
Abstract
本発明は、全色素分に対して、25〜80重量%の下記構造式[1]で示される黄色系色素および75〜20重量%の下記構造式[2]で示される黄色系色素を含有する染料混合物に関する。
【化1】
[式中RはC1〜C4ヒドロキシアルキル基を表す。]The present invention contains 25 to 80% by weight of a yellow dye represented by the following structural formula [1] and 75 to 20% by weight of a yellow dye represented by the following structural formula [2] based on the total pigment content. It relates to a dye mixture.
[Chemical 1]
Wherein R represents C 1 -C 4 hydroxyalkyl groups. ]
Description
本発明は、ポリエステル系繊維を耐光堅牢度に優れる良好な黄色に染色することができ、且つ、染色温度依存性が小さい、分散染料に関するものである。 The present invention relates to a disperse dye capable of dyeing a polyester fiber into a good yellow color having excellent light fastness and having a low dyeing temperature dependency.
自動車シートの材質としてはポリエステル繊維よりなる布が多用されているが、近年の自動車内装のファッション性の向上に伴い、シート色の豊富さが要求されるようになった。しかし、自動車シートは密閉室内で高温下に日光に曝されることが多く、そのためシートの色あせが起こり易く、長期間良好な色を確実に維持することは難しい。従って、自動車シートに使用されるポリエステル繊維を染色するためには、耐光堅牢度に特に優れた染料を用いなければならない。 As materials for automobile seats, fabrics made of polyester fibers are often used. However, with the recent improvement in fashionability of automobile interiors, abundant seat colors are required. However, automobile seats are often exposed to sunlight at high temperatures in a sealed room, so that the seats tend to fade and it is difficult to reliably maintain a good color for a long period of time. Therefore, in order to dye the polyester fiber used for the automobile seat, a dye having particularly excellent light fastness must be used.
ところが、従来、耐光堅牢度に特に優れ、なおかつ染色温度依存性の小さい、すなわち、染色に適した温度範囲が広く、染色時の再現性及び温度管理が容易な黄色染料は少なく、自動車シート用黄色染料として満足できるものはあまり見当たらない。例えば、前記構造式[1]で示される色素は、特許文献1や特許文献2により公知であるが、この色素は耐光堅牢度の面では優れており、自動車シート用のポリエステル繊維の染色には一応適用できるものの、染色温度依存性が大きく染色時の温度管理が難しい。また、前記構造式[2]で示される色素は特許文献3や特許文献4により公知であるが、この色素は染色温度依存性は小さいものの、自動車シート材料に用いられる場合、耐光堅牢度に問題がある。 However, conventionally, it is particularly excellent in light fastness and has little dependency on dyeing temperature, that is, a wide temperature range suitable for dyeing, and there are few yellow dyes that are easy to reproduce and temperature control during dyeing. There are not many satisfactory dyes. For example, the dye represented by the structural formula [1] is known from Patent Documents 1 and 2, but this dye is excellent in terms of light fastness, and is used for dyeing polyester fibers for automobile seats. Although it can be applied once, it is highly dependent on the dyeing temperature and it is difficult to control the temperature during dyeing. Further, the dye represented by the structural formula [2] is known from Patent Document 3 and Patent Document 4, but this dye has a small dyeing temperature dependency, but has a problem in light fastness when used in an automobile sheet material. There is.
本発明者等は、上記実状に鑑み耐光堅牢度が良好であり且つ染色温度依存性が小さい、自動車シート用のポリエステル系繊維を染色するのに適した黄色系染料を提供することを目的として鋭意検討の結果、本発明の特定の染料混合物が上記目的を達成することを見出した。 In light of the above circumstances, the present inventors have earnestly aimed to provide a yellow dye suitable for dyeing polyester fiber for automobile seats, which has good light fastness and low dyeing temperature dependency. As a result of investigation, it was found that the specific dye mixture of the present invention achieves the above-mentioned object.
本発明者等は、下記構造式[1]で示される黄色系色素の優れた耐光堅牢度を維持しつつ染色温度依存性を小さくする方法について種々検討を行った結果、下記構造式[1]で示される色素に下記構造式[2]またはこれに加えて[3] で示される色素を混合して用いると、下記構造式[1]の色素単独の場合に比べて染色温度依存性が小さくなるのみならず、耐光堅牢度も向上する場合があることを見出し、本発明を完成した。 The present inventors have conducted various studies on methods for reducing the dyeing temperature dependency while maintaining the excellent light fastness of the yellow dye represented by the following structural formula [1]. As a result, the following structural formula [1] When the dye represented by the following structural formula [2] or the dye represented by [3] is used in combination with the dye represented by the following formula, the dyeing temperature dependency is less than that of the dye represented by the following structural formula [1] alone. In addition, the present inventors have found that the light fastness may be improved, and completed the present invention.
本発明によれば、下記構造式[1]に示される色素に下記構造式[2]若しくはこれに加えて下記構造式[3]で示される色素を混合することにより、式[1]で示される色素の良好な耐光堅牢度を維持しつつ、染色温度依存性が大幅に改善された黄色系分散染料混合物が得られる。 According to the present invention, the dye represented by the following structural formula [1] is mixed with the dye represented by the following structural formula [2] or in addition to the dye represented by the following structural formula [3]. A yellow disperse dye mixture having significantly improved dyeing temperature dependency while maintaining good light fastness of the dye to be obtained is obtained.
即ち、本発明は、全色素分に対して、25〜80重量%の下記構造式[1]で示される黄色系色素および75〜20重量%の下記構造式[2]で示される黄色系色素(但し、RはC1〜C4ヒドロキシアルキル基を表す)を含有する染料混合物に関する。該染料混合物は、好ましくは、50〜70重量%の前記構造式[1]で示される黄色系色素および50〜30重量%の前記構造式[2]で示される黄色系色素を含有する。 That is, the present invention relates to a yellow pigment represented by the following structural formula [1] of 25 to 80% by weight and a yellow pigment represented by the following structural formula [2] of 75 to 20% by weight based on the total pigment content. (wherein, R represents a C 1 -C 4 hydroxyalkyl group) relates to dye mixtures comprising a. The dye mixture preferably contains 50 to 70% by weight of the yellow pigment represented by the structural formula [1] and 50 to 30% by weight of the yellow pigment represented by the structural formula [2].
前記構造式[2]で示される色素の混合割合があまり少ない場合には、染色温度依存性の改善効果は小さい。また逆に、前記構造式[2]で示される色素の混合割合があまり多すぎる場合には、耐光堅牢度の低下を招く。 When the mixing ratio of the dye represented by the structural formula [2] is too small, the effect of improving the dyeing temperature dependency is small. Conversely, when the mixing ratio of the dye represented by the structural formula [2] is too large, the light fastness is lowered.
本発明の1つの好ましい形態として、全色素分に対して20重量%以下の下記構造式[3]で示される黄色系色素を更に含有する前記染料混合物がある。 As one preferable embodiment of the present invention, there is the dye mixture further containing a yellow pigment represented by the following structural formula [3] of 20% by weight or less based on the total pigment content.
特に好ましくは、全色素分に対して5〜15重量%以下の前記構造式[3]で示される黄色系色素を含有する前記染料混合物である。 Particularly preferred is the dye mixture containing 5 to 15% by weight or less of the yellow pigment represented by the structural formula [3] based on the total pigment content.
更に、所望の色に染色するために必要な量の赤色色素及び青色色素を含有してもよい。
所望の量の前記構造式[1]、[2]及び[3]の色素を混合することにより、本発明の染料混合物を容易に得ることができる。
Further, it may contain red and blue dyes in an amount necessary for dyeing to a desired color.
The dye mixture of the present invention can be easily obtained by mixing desired amounts of the dyes of the structural formulas [1], [2] and [3].
本発明の染料混合物を用いてポリエステル繊維を染色するためには、前記構造式[1]、[2]及び[3]の色素は水に不溶若しくは難溶であるので、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、高級アルコール硫酸エステル、高級アルキルベンゼンスルホン酸塩等を使用し、水性媒質中にそれらを微粒子化して分散させた染色浴又は捺染糊を調製し、その後、浸染又は捺染によって染色が可能となる。例えば、浸染の場合、高温染色法、キャリヤー染色法、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乃至はその混紡品に堅牢度の優れた染色を施すことができる。 In order to dye polyester fibers using the dye mixture of the present invention, the pigments of the structural formulas [1], [2] and [3] are insoluble or sparingly soluble in water. Condensate of formaldehyde, higher alcohol sulfate, higher alkylbenzene sulfonate, etc. are used to prepare a dyeing bath or printing paste in which they are finely dispersed in an aqueous medium, and then dyed by dip dyeing or printing. Is possible. For example, in the case of dip dyeing, if a normal dyeing method such as a high temperature dyeing method, a carrier dyeing method, or a thermosol dyeing method is applied, dyeing with excellent fastness can be applied to a polyester fiber or a blended product thereof.
実施例1〜7、並びに比較例1及び2
前記構造式[1]、[3]及び下記構造式[2−1]、[2−2]、[2−3]で示される色素を表1記載の割合で混合した。
Examples 1-7 and Comparative Examples 1 and 2
The dyes represented by the structural formulas [1] and [3] and the following structural formulas [2-1], [2-2], and [2-3] were mixed at a ratio shown in Table 1.
この色素混合物16mgとナフタレンスルホン酸/ホルムアルデヒド縮合物、高級アルコール硫酸エステル等で構成される分散剤49mgを混合し、これを染色助剤及び酢酸/酢酸ナトリウムpH緩衝液を含む水100mlに分散させ調整した染色浴に、ポリエステル布5gを浸漬し、135℃で30分染色した後、常法により還元洗浄、水洗及び乾燥を行ったところ、黄色の染色物が得られた。この染色物の耐光堅牢度を、トヨタ自動車株式会社の耐光堅牢度試験規格により評価したところ、請求項1〜3に記載の混合比率である実施例1〜7のものは耐光堅牢度が良好であった。特に前記構造式[1]及び[2]で示される色素をそれぞれ55重量%及び45重量%で混合した実施例1、5及び6、並びにそれぞれ65重量%及び35重量%で混合した実施例7のものは、構造式[1]の色素を単独で用いた場合よりも耐光堅牢度が向上していた。なお、この耐光堅牢度試験は、試験装置としてスガ試験機株式会社の強エネルギーキセノンフェードメーターを使用し、照射強度150W/m2(300〜400nm)、照射時間3.8時間/暗時間1時間を1サイクルとして38サイクル(182時間)の明暗法による照射をブラックパネル温度73±3℃の条件下で行った。試験布はウレタンで裏打ちした上で試験を行った。 16 mg of this dye mixture was mixed with 49 mg of a dispersant composed of naphthalenesulfonic acid / formaldehyde condensate, higher alcohol sulfate, etc., and this was dispersed in 100 ml of water containing a dyeing assistant and acetic acid / sodium acetate pH buffer solution. After 5 g of polyester cloth was immersed in the dyeing bath and dyed at 135 ° C. for 30 minutes, it was subjected to reduction washing, water washing and drying by a conventional method, whereby a yellow dyeing was obtained. When the light fastness of the dyed product was evaluated according to the light fastness test standard of Toyota Motor Corporation, the light fastness of Examples 1 to 7 having the mixing ratio according to claims 1 to 3 was good. there were. Particularly, Examples 1, 5 and 6 in which the dyes represented by the structural formulas [1] and [2] were mixed at 55% by weight and 45% by weight, respectively, and Example 7 in which 65% and 35% by weight were mixed, respectively. In the case of No. 1, the light fastness was improved as compared with the case where the dye of the structural formula [1] was used alone. In addition, this light fastness test uses a strong energy xenon fade meter of Suga Test Instruments Co., Ltd. as a test device, irradiation intensity 150 W / m 2 (300 to 400 nm), irradiation time 3.8 hours / dark time 1 hour. As one cycle, irradiation by the light and dark method for 38 cycles (182 hours) was performed under the condition of a black panel temperature of 73 ± 3 ° C. The test cloth was tested after being lined with urethane.
次に、染色温度依存性の評価を下記の方法で行った。先の耐光堅牢度評価時と同様の色素を表1記載の割合で混合した。この色素混合物29mgをナフタレンスルホン酸/ホルムアルデヒド縮合物、高級アルコール硫酸エステル等で構成される分散剤86mgと混合し、これを染色助剤及び酢酸/酢酸ナトリウムpH緩衝液を含む水100mlに分散させ調整した染色浴に、ポリエステル布5gを浸漬し、130℃で30分若しくは120℃で30分染色した後、それぞれ常法により還元洗浄、水洗及び乾燥を行い染色物を得た。120℃での染色物の濃度を、130℃染色物の濃度に対して比較したところ、請求項1〜3に記載の混合比率である実施例1〜7の染色物については、130℃で染色した場合と120℃で染色した場合の濃度の違いは少なく、温度依存性が小さいことを示している。一方、構造式[1]で示される色素を単独で用いた比較例1の場合、この濃度差が大きく染色温度依存性が大きい、即ち、染色に適した温度の範囲が狭く、染色時の再現性・温度管理が難しいことを示している。 Next, the dyeing temperature dependency was evaluated by the following method. The same pigments as those used in the previous light fastness evaluation were mixed in the proportions shown in Table 1. 29 mg of this dye mixture is mixed with 86 mg of a dispersant composed of naphthalenesulfonic acid / formaldehyde condensate, higher alcohol sulfate, etc., and dispersed in 100 ml of water containing a dyeing assistant and acetic acid / sodium acetate pH buffer solution to prepare. After 5 g of the polyester cloth was immersed in the dyeing bath and dyed at 130 ° C. for 30 minutes or 120 ° C. for 30 minutes, reduction washing, washing with water and drying were performed in the usual manner to obtain a dyed product. When the density of the dyed product at 120 ° C. was compared with the density of the 130 ° C. dyed product, the dyed product of Examples 1 to 7 having the mixing ratio according to claim 1 to 3 was dyed at 130 ° C. The difference between the density when dyed at 120 ° C. and that when dyed at 120 ° C. is small, indicating that the temperature dependence is small. On the other hand, in the case of Comparative Example 1 in which the dye represented by the structural formula [1] is used alone, this density difference is large and the dependency on the dyeing temperature is large, that is, the temperature range suitable for dyeing is narrow, and reproduction at the time of dyeing is performed. This indicates that it is difficult to manage temperature and temperature.
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PCT/EP2003/008582 WO2004018567A1 (en) | 2002-08-08 | 2003-08-02 | Yellow disperse dye mixture which has a high level of light fastness |
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