Disperse orange dye composition, dye product and application thereof

Abstract

The invention discloses a disperse orange dye composition, a dye product and application thereof. The disperse orange dye composition comprises a component A and a component B, the component A is selected from at least one of dyes shown in a formula (I), the component B is selected from at least one of dyes shown in a formula (II), the mass percentage content of the component A is 1-99%, and the mass percentage content of the component B is 1-99%. The invention provides a disperse orange dye product, which contains the disperse orange dye composition and an auxiliary agent, and provides an application of the disperse orange dye product in the dyeing of a polylactic acid fiber material, and the disperse orange dye product has the characteristics of high dye uptake, good lifting power, good deep color dyeing property, excellent color fastness and the like. (I) (II)

Description

Technical Field

[0001] This invention belongs to the field of disperse dyes, and particularly relates to a disperse orange dye composition and dye product, as well as the dyeing application of the dye product on hydrophobic fiber materials, especially polylactic acid fiber materials and their blended fabrics. Background Technology

[0002] Polylactic acid (PLA), commonly known as "corn fiber," is a bio-based polymer derived from renewable plant resources such as corn starch and sugarcane. PLA also possesses a silk-like luster and a naturally skin-friendly feel, earning it the reputation of "breathable fiber." It is particularly suitable for making intimate apparel. Due to its unique physical properties, this fiber is reshaping the application landscape of modern textile fabrics, and with global focus on carbon emissions, the market demand for PLA fiber is growing rapidly.

[0003] Currently, PLA fibers face challenges in dyeing and finishing. Compared to traditional cotton and polyester, they are extremely sensitive to temperature, pH, and dye type, and there are compatibility issues with conventional disperse dyes. Disperse dyes are commonly used for dyeing polyester fibers, but their performance on PLA fibers differs significantly from that of traditional polyester (PET) fibers. PLA fibers have high crystallinity, a compact molecular structure, and small fiber micropores, making it difficult for disperse dye molecules to penetrate the fiber interior, resulting in generally low dye uptake. Furthermore, many disperse dyes that perform well on PET fibers exhibit poor colorfastness and other dyeing properties on PLA fibers, leading to a scarcity of suitable disperse dyes for PLA fibers. This compatibility issue limits the application of PLA fibers in the textile industry. Therefore, studying the interaction between the two and finding suitable disperse dyes is crucial for promoting the widespread adoption of PLA fibers. Summary of the Invention

[0004] To address the above-mentioned problems, the present invention provides a disperse orange dye composition and dye product, as well as its application in the dyeing of polylactic acid fibers. When the dye product is applied to the dyeing of polylactic acid fibers, it has the characteristics of high dyeing rate and excellent color fastness.

[0005] The technical solution adopted in this invention is as follows: A disperse orange dye composition comprising component A and component B, wherein component A is selected from at least one of the dyes shown in formula (I), and component B is selected from at least one of the dyes shown in formula (II), wherein the mass percentage of component A is 1-99%, and the mass percentage of component B is 1-99%. (I) (II) In formula (I): X1 X 2 Each can be independently H, Cl, or Br, with Cl or Br being preferred; R 1 It is a C1 to C4 alkyl group; m and n are each independently 1 or 2; Ph stands for phenyl; In formula (II): X 3 X 4 Each can be H, Cl, or Br, with H or Cl being preferred.

[0006] The C1-C4 alkyl groups described in this invention can be straight-chain or branched alkyl groups, preferably methyl, ethyl, propyl or butyl.

[0007] In some embodiments, the disperse orange dye composition contains component A at a mass percentage of 20-85% and component B at a mass percentage of 15-80%. Further, component A contains 30-80% and component B contains 20-70% by mass.

[0008] Preferably, in the disperse orange dye composition of the present invention, component A is selected from at least one of the dyes shown in formulas (I-1) to (I-12): (I-1) (I-2) (I-3) (I-4) (I-5) (I-6) (I-7) (I-8) (I-9) (I-10) (I-11) (I-12).

[0009] Preferably, in the disperse orange dye composition of the present invention, component B is selected from at least one of the dyes shown in formulas (II-1) to (II-4): (II-1) (II-2) (II-3) (II-4).

[0010] Preferably, the disperse orange dye composition comprises component A and component B. Further, the mass percentage of component A is 5-95%, and the mass percentage of component B is 5-95%.

[0011] As a further preferred embodiment, the disperse orange dye composition comprises component A and component B, wherein component A has a mass percentage content of 5-95%, and component B has a mass percentage content of 5-95%, wherein: Component A is selected from at least one of the dyes shown in formulas (I-1), (I-2), and (I-6).

[0012] Component B is selected from at least one of the dyes shown in formulas (II-1) and (II-2).

[0013] The disperse orange dye composition of the present invention also allows the addition of other tinting components, such as CI Disperse Orange 61, for further compounding and enhancement, provided that the amount of tinting component added does not exceed 20% of the total amount of dye.

[0014] In this invention, the dyes shown in formulas (I) and (II) can be conveniently synthesized using common chemicals, dye precursors, or intermediates in accordance with diazotization and coupling methods well known to those skilled in the art.

[0015] The disperse orange dye composition of this invention typically requires the addition of conventional auxiliaries during application. Therefore, this invention also provides a disperse orange dye product containing the aforementioned disperse orange dye composition and auxiliaries, with the weight ratio of auxiliaries to the disperse orange dye composition being (0.3~3):1. The auxiliaries are dispersants, diffusion agents, and other surfactants commonly used in disperse dye compounding, preferably selected from one or more of the following in any proportion: naphthalene sulfonate formaldehyde condensate (e.g., diffusion agent NNO), lignin sulfonate (e.g., sodium lignin sulfonate), alkyl naphthalene sulfonate formaldehyde condensate [e.g., methyl naphthalene sulfonate formaldehyde condensate (dispersant MF)], benzyl naphthalene sulfonate formaldehyde condensate (e.g., diffusion agent CNF), sodium sulfate, etc.

[0016] The preparation method of the disperse orange dye product of the present invention is as follows: The dyes (i.e., the primary dyes) constituting the disperse orange dye composition are mixed in the aforementioned proportions, then auxiliaries and water are added, and the mixture is micronized using a sand mill or grinding mill. Alternatively, each dye can be micronized separately in the presence of auxiliaries and water using a sand mill or grinding mill, and then mixed in the aforementioned proportions. After the above treatment, the resulting liquid product can be used directly, or it can be further spray-dried to obtain powdered or granular products. This is a preparation method known to those skilled in the art. It is understood that since water cannot be completely removed during spray drying, a certain amount of water is still allowed in the powdered and granular dye products, preferably not exceeding 10% of the total weight of the dye product. The disperse orange dye product of the present invention can be used directly in the above-mentioned liquid, powdered, or granular product form or as a commercial dye.

[0017] The disperse orange dye product of this invention can be applied to the printing and dyeing of hydrophobic fiber materials. It should be noted that the technical feature contributing to the improvement of the dyeing effect when the disperse orange dye product of this invention is applied to the printing and dyeing of hydrophobic fiber materials lies in the disperse orange dye composition contained in the product.

[0018] This invention provides the application of the disperse orange dye product in the dyeing of polylactic acid fiber materials.

[0019] Dyed products made using the dye composition of the present invention can be used to dye polylactic acid textile materials (such as polylactic acid fabrics and polylactic acid fibers) in accordance with industry-standard methods, such as high-temperature and high-pressure dyeing. In high-temperature and high-pressure dyeing, the polylactic acid textile material is first pretreated and then placed in a high-temperature and high-pressure infrared dyeing machine for dyeing. After dyeing, it is washed with water until neutral, then subjected to reduction cleaning, followed by water washing, acid washing until neutral, and finally water washing and drying to obtain the dyed fabric sample.

[0020] Compared with the prior art, the beneficial effects of the present invention are as follows: the disperse orange dye composition and dye product provided by the present invention have the characteristics of high dyeing rate, good lifting power, good color depth and excellent color fastness when dyeing polylactic acid fiber materials. Attached Figure Description

[0021] Figure 1 This is the result of the lifting force of the dye products prepared in Examples 1 and 2 of the present invention. Detailed Implementation

[0022] The present invention will be further described below with reference to specific embodiments, but the scope of protection of the present invention is not limited thereto: Example 1 Add 50g of the dye shown in formula (Ⅰ-1), 50g of the dye shown in formula (Ⅱ-1), and 155g of dispersant MF to 425g of water for pre-dispersion. Then grind, disperse, and dry to obtain the finished product. The finished product can provide the orange hue of polylactic acid and its blended fabrics (the weights of dye and dispersant are on dry weight, the same below).

[0023] (I-1) (II-1) Example 2 Mix 80 grams of the dye shown in formula (Ⅰ-1), 20 grams of the dye shown in formula (Ⅱ-2), and 165 grams of dispersant NNO with 450 grams of water, pre-disperse, grind, disperse, and dry to obtain the finished product. This finished product can provide an orange hue for polylactic acid and its blended fabrics.

[0024] (I-1) (II-2) Example 3 Add 30 grams of the dye shown in formula (Ⅰ-1), 70 grams of the dye shown in formula (Ⅱ-2), and 150 grams of the dispersant sodium lignosulfonate to 450g of water for pre-dispersion. Then grind, disperse, and dry to obtain the finished product, which can provide an orange hue for polylactic acid and its blended fabrics.

[0025] (I-1) (II-2) Example 4-20 Following the method described in Example 1, using the dye structure and weight ratio shown in Component A and Component B of Table 1, 180 grams of auxiliaries (100 grams of dispersant NNO and 80 grams of sodium lignosulfonate) were added, and 500 grams of water were added to mix and disperse the dye to form a slurry. The slurry was then ground, dispersed, and dried to obtain the finished product. This dye can achieve high uptake on polylactic acid and its blended fabrics and provides an orange hue with excellent color fastness.

[0026] Table 1. Components A and B and their weight ratios

[0027] Example 21

[0028] Add 45g of the dye shown in formula (Ⅰ-1), 45g of the dye shown in formula (Ⅱ-1), 10g of CI Disperse Orange 61, and 155g of dispersant MF to 425g of water for pre-dispersion. Then grind, disperse, and dry to obtain the finished product, which can provide an orange hue for polylactic acid and its blended fabrics.

[0029] (I-1) (II-1) Staining Example 1 0.5 grams of the disperse orange dye product prepared according to the methods described in Examples 1-20 were weighed and dyed onto polylactic acid fiber fabrics using a conventional high-temperature and high-pressure dyeing method. During the dyeing process, the dyeing depth (owf) was controlled at 2.0%, the liquor ratio was 1:20, the pH of the dye liquor was adjusted to 4.0-5.0 using acetic acid, and dyeing was carried out at room temperature. The temperature was increased to 60°C at a rate of 2°C / min and held for 10 min, then slowly increased to 110°C at a rate of 1°C / min and held for 30 min for dyeing. After dyeing, the fabric was washed with water, reduced cleaning, washed again with water, acid-washed to neutral, and finally washed and dried to obtain the dyed fabric sample.

[0030] 1. Dyeing rate determination

[0031] Transfer the mother liquor before staining, add DMF, and measure the absorbance at the maximum absorption wavelength using a UV-Vis spectrophotometer. 初 ; Transfer the residual staining solution, add DMF, and measure the absorbance at the maximum absorption wavelength as A. 残 , Dyeing rate (%) = (1-m) 初 ×M 残 ×A 残 / (m 残 ×M 初 ×A 初 ))×100% m 初 : This refers to the mass of the mother liquor before staining, in grams; M 初 : Total mass of the mother liquor and added DMF before staining, in g; m 残 : Mass of residual solution after staining, in grams; M 残 : Total mass of residual solution after staining and added DMF, g.

[0032] The results of the dyeing rate test are shown in Table 2.

[0033] 2. The dyed fabric samples obtained in Dyeing Example 1 were tested for their light fastness (AATCC-16), rubbing fastness (ISO 105-X12), and washing fastness (ISO 105-C03). The test results are shown in Table 2.

[0034] Table 2 Test Data of Dyed Fabric Samples

[0035] 3. Lifting force test: Following the method described in Dyeing Example 1, the dye products prepared in Examples 1 and 2 of this invention were used to dye polylactic acid (PLA) fabric and polyester (PET) fabric respectively within the dyeing concentration range of 0.5% to 6.0% and under pH 4.5 conditions. The lifting force was tested according to the method described in GB / T 2397, and the lifting force results are shown in Figure 1.

[0036] As can be seen from the test results, the disperse dye products described in this invention maintain good dyeing rate and dyeing performance when applied to the dyeing of polylactic acid and its blended fabrics. Compared with the application to polyester dyeing, its lifting power is significantly improved, which can solve the compatibility problem between disperse dyes and polylactic acid fibers.

Claims

1. A disperse orange dye composition, characterized in that: The disperse orange dye composition comprises component A and component B, wherein component A is selected from at least one of the dyes shown in formula (I), and component B is selected from at least one of the dyes shown in formula (II), wherein the mass percentage of component A is 1-99%, and the mass percentage of component B is 1-99%. （I） (II) In formula (I): X 1 X 2 Each can be independently H, Cl, or Br; R 1 It is a C1 to C4 alkyl group; m and n are each independently 1 or 2; Ph stands for phenyl; In formula (II): X 3 X 4 Each can be H, Cl, or Br independently.

2. The disperse orange dye composition according to claim 1, characterized in that: Component A is selected from at least one of the dyes shown in formulas (I-1) to (I-12): （I-1） （I-2） （I-3） （I-4） （I-5） （I-6） （I-7） （I-8） （I-9） （I-10） （I-11） （I-12）。 3. The disperse orange dye composition according to claim 1, characterized in that: Component B is selected from at least one of the dyes shown in formulas (II-1) to (II-4): (II-1) (II-2) (II-3) (II-4)。 4. The disperse orange dye composition according to any one of claims 1-3, characterized in that: The disperse orange dye composition consists of component A and component B.

5. The disperse orange dye composition according to claim 4, characterized in that: In the disperse orange dye composition, the mass percentage of component A is 5-95%, and the mass percentage of component B is 5-95%.

6. The disperse orange dye composition according to claim 1, characterized in that: The disperse orange dye composition comprises component A and component B, wherein component A has a mass percentage of 5-95% and component B has a mass percentage of 5-95%, wherein: Component A is selected from at least one of the dyes shown in formulas (I-1), (I-2), and (I-6). Component B is selected from at least one of the dyes shown in formulas (II-1) and (II-2); （I-1） （I-2） （I-6） (II-1) (II-2)。 7. A disperse orange dye product comprising the disperse orange dye composition and auxiliaries as described in any one of claims 1-6.

8. The disperse orange dye product as described in claim 7, characterized in that: The weight ratio of the auxiliary agent to the disperse orange dye composition is (0.3~3):

1.

9. The disperse orange dye product as described in claim 7, characterized in that: The additives are selected from one or more of the following in any proportion: naphthalene sulfonate formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonate formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, and sodium sulfate.

10. The application of the disperse orange dye product as described in claim 7 in the dyeing of polylactic acid fiber materials.

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