JP4394000B2 - Yellow disperse dye mixture with high light fastness - Google Patents

Description

  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.

  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 in the automobile seat, a dye that is particularly excellent in light fastness must be used.

  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 reproducible and temperature control during dyeing, and yellow for automobile seats. 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.

British Patent No. 1105568 Japanese Patent Publication No. 4-24470 German Patent No. 2212755 Japanese Patent No. 2,506,594

  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.

  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.

  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]. Thus, a yellow disperse dye mixture having significantly improved dyeing temperature dependency can be obtained while maintaining good light fastness of the dye.

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) it 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].

  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.

  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.

  Particularly preferably, the dye mixture contains 5 to 15% by weight or less of the yellow pigment represented by the structural formula [3] based on the total pigment content.

Further, it may contain a red pigment and a blue pigment in an amount necessary for dyeing to a desired color.
The dye mixture of the present invention can be easily obtained by mixing a desired amount of the dyes of the structural formulas [1], [2] and [3].

  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.

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 in the proportions shown in Table 1.

16 mg of this dye mixture was mixed with 49 mg of a dispersant composed of naphthalene sulfonic 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 a light and dark method for 38 cycles (182 hours) was performed at a black panel temperature of 73 ± 3 ° C. The test cloth was tested after being lined with urethane.

  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 this is 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 130 ° C. for 30 minutes or at 120 ° C. for 30 minutes, they were each subjected to reduction washing, washing with water and drying to obtain dyeings. When the density | concentration of the dyeing | staining thing in 120 degreeC was compared with the density | concentration of 130 degreeC dyeing | staining, it dye | stained at 130 degreeC about the dyeing | staining thing of Examples 1-7 which is the mixing ratio of Claims 1-3. The difference in the density when dyed at 120 ° C. is small, indicating that the temperature dependency 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, the 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 the temperature and temperature.

Claims (4)

A dye mixture containing 25 to 80% by weight of a yellow pigment represented by the following structural formula [1] and 75 to 20% by weight of a yellow pigment represented by the following structural formula [2] based on the total pigment content.

Wherein R represents C ₁ -C ₄ hydroxyalkyl groups. ]   2. The dye mixture according to claim 1, comprising 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]. The dye mixture according to claim 1 or 2, comprising a yellow pigment represented by the following structural formula [3] of 15 wt% or less based on the total pigment content.

  The dyeing | staining method of the polyester-type fiber using the dye mixture as described in any one of Claims 1-3.