Disperse orange-to-red dye composition, dye product and application thereof

Abstract

The invention discloses a disperse orange-to-red dye composition, a dye product and application thereof. The disperse orange-to-red 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-to-red dye product which contains the disperse orange-to-red dye composition and an auxiliary agent, and provides application of the disperse orange-to-red dye product in dyeing of a polylactic acid fiber material, and the disperse orange-to-red dye product has the characteristics of high dye uptake, 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 to red 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) fiber is an environmentally friendly synthetic fiber, mainly composed of lactic acid polymer obtained from corn starch fermentation. It has a melting point of approximately 175°C and a glass transition temperature of around 55°C. This fiber possesses antibacterial, anti-mite, and anti-allergenic properties, along with excellent moisture absorption and breathability, keeping skin dry and providing high wearing comfort. It is gaining increasing consumer acceptance and has a promising market prospect. However, PLA fiber contains a large number of ester and methyl groups, resulting in poor alkali resistance. Furthermore, it lacks hydrophilic polar and reactive groups. Therefore, it is currently mostly dyed with disperse dyes. However, the high crystallinity of PLA fiber makes it difficult for dye molecules to diffuse into the fiber interior, leading to lower dye uptake and color fastness compared to traditional fibers, with more light colors and fewer dark colors, and lower color vibrancy. Therefore, improving the dye uptake and fastness of PLA fiber is one of the main research directions for those skilled in the art. Summary of the Invention

[0003] To address the aforementioned problems, this invention provides a disperse orange to red 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.

[0004] The technical solution adopted in this invention is as follows: The present invention provides a disperse orange to red 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 to 99%, and the mass percentage of component B is 1 to 99%. (I) (II) In formula (I): X 1 It is a halogen; R 1 R 2 Each is an independent C1 to C4 alkyl group; In formula (II): X 2 X 3 Each can be either hydrogen or halogen.

[0005] The C1-C4 alkyl groups described in this invention can be straight-chain or branched alkyl groups, preferably methyl, ethyl, propyl, or butyl. The halogen can be fluorine, chlorine, bromine, or iodine, preferably chlorine or bromine.

[0006] In some embodiments, the disperse orange to red dye composition contains component A at a mass percentage of 10-90% and component B at a mass percentage of 10-90%. Further, component A contains a mass percentage of 30-80% and component B contains a mass percentage of 20-70%.

[0007] Preferably, in the disperse orange to red dye composition of the present invention, component A is selected from at least one of the dyes shown in formulas (I-1) to (I-5): (I-1) (I-2) (I-3) (I-4) (I-5).

[0008] Preferably, in the disperse orange to red dye composition of the present invention, component B is selected from at least one of the dyes shown in formulas (II-1) to (II-3): (II-1) (II-2) (II-3).

[0009] Preferably, the disperse orange to red dye composition comprises component A and component B. Further, the mass percentage of component A is 10-90%, and the mass percentage of component B is 10-90%.

[0010] As a further preferred embodiment, the disperse orange to red dye composition comprises component A and component B, wherein component A has a mass percentage content of 10-90%, and component B has a mass percentage content of 10-90%, wherein: Component A is selected from at least one of formulas (I-1), (I-2), and (I-3); Component B is selected from at least one of formulas (II-1) and (II-2).

[0011] The disperse orange to red dye composition of the present invention also allows the addition of other tinting components, such as CI Disperse Red 73, for further compounding and enhancement, provided that the amount of tinting component added does not exceed 20% of the total amount of dye.

[0012] In this invention, the dyes shown in formula (I) and formula (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.

[0013] The disperse orange to red dye composition of the present invention typically requires the addition of conventional auxiliaries during application. Therefore, the present invention also provides a disperse orange to red dye product containing the aforementioned disperse orange to red dye composition and auxiliaries. The weight ratio of the auxiliaries to the disperse orange to red dye composition is generally (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, lignin sulfonate, alkyl naphthalene sulfonate formaldehyde condensate [such as methyl naphthalene sulfonate formaldehyde condensate (dispersant MF)], naphthalene sulfonate formaldehyde condensate (diffusion agent NNO), benzyl naphthalene sulfonate formaldehyde condensate (diffusion agent CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), etc.

[0014] The preparation method of the disperse orange to red dye product of the present invention is as follows: The dye monomers (original dyes) constituting the disperse orange to red dye composition are mixed in the aforementioned proportion, then auxiliaries and water are added, and the mixture is micronized using a sand mill or grinding mill. Alternatively, the dye monomers can be micronized separately in the presence of auxiliaries and water using a sand mill or grinding mill, and then mixed in the aforementioned proportion. After the above treatment, the resulting liquid product can exist directly in liquid form, or it can be further spray-dried to obtain powder 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 powder and granular dye products, preferably not exceeding 10% of the total weight of the dye product. The disperse orange to red dye product of the present invention can be directly applied or used as a commercial dye in the aforementioned liquid, powder, or granular product forms.

[0015] The disperse orange to red 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 to red dye product of this invention is applied to the printing and dyeing of hydrophobic fiber materials lies in the disperse orange to red dye composition contained in the product.

[0016] This invention provides the application of the disperse orange to red dye product in the dyeing of polylactic acid fiber materials.

[0017] Dyed products made using the dye composition of this 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 before being placed in a high-temperature and high-pressure infrared dyeing machine. 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.

[0018] Compared with the prior art, the beneficial effects of the present invention are as follows: the disperse orange to red dye composition and dye product provided by the present invention have the characteristics of high dyeing rate, good dyeing depth and excellent color fastness when dyeing polylactic acid fiber materials. Attached Figure Description

[0019] Figure 1 This is the result of the lifting force of the dye products prepared in Examples 1 and 9 of the present invention. Detailed Implementation

[0020] 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 165g of dispersant MF to 600g of water for pre-dispersion. Then grind, disperse, and dry to obtain the finished product. The finished product can provide red hues for polylactic acid and its blended fabrics (the weights of dye and dispersant are on dry weight, the same below).

[0021] (I-1) (II-1) Example 2: Add 80g of the dye shown in formula (Ⅰ-1), 20g of the dye shown in formula (Ⅱ-2), 170g of dispersant MF, and 3g of CI Disperse Red 73 to 550g of water, mix and pre-disperse, grind and disperse, and dry to obtain the finished product. The finished product can provide red hues for polylactic acid and its blended fabrics (the weights of dyes and dispersants are all on dry weight, the same below).

[0022] (I-1) (II-2) Examples 3-10 Following the method described in Examples 1-2, using the dye structure and weight ratio shown in Component A and Component B of Table 1, 155 grams of auxiliaries (55 grams of dispersant NNO and 100 grams of sodium lignosulfonate) were added, and 1000 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 dyeing rates on polylactic acid and its blended fabrics and provides orange to red hues with excellent color fastness.

[0023] Table 1 Weight ratio of component A and component B

[0024] Staining Example 1: 0.5 g of each of the disperse orange to red dye products prepared according to the methods described in Examples 1-10 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 40 min for dyeing. After dyeing, the fabric samples were washed with water, reduced washing, washed again with water, acid washed to neutral, and finally washed and dried to obtain the dyed fabric samples.

[0025] 1. The light fastness (AATCC-16), rubbing fastness (ISO 105-X12), and washing fastness (ISO 105-C03) of the dyed fabric samples were determined. The test results are shown in Table 2.

[0026] 2. Dyeing rate determination: 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%.

[0027] Where, 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 grams; m 残 : Mass of residual solution after staining, in grams; M 残: Total mass of residual solution after staining and added DMF, g.

[0028] The results of the dyeing rate test are shown in Table 2.

[0029] Table 2 Test Data of Dyed Fabric Samples

[0030] 3. Lifting force test: Following the method described in Dyeing Example 1, the dye products prepared in Examples 1 and 9 of this invention were used to dye polylactic acid fabric (PLA) and polyester fabric (PET) 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.

[0031] As can be seen from the test results, the disperse dye products described in this invention, when applied to the dyeing of polylactic acid and its blended fabrics, show a significant improvement in lifting power compared to their application in polyester dyeing.

Claims

1. A disperse orange to red dye composition, characterized in that: The disperse orange to red 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 to 99%, and the mass percentage of component B is 1 to 99%. （I） (II) In formula (I): X 1 It is a halogen; R 1 R 2 Each is an independent C1 to C4 alkyl group; In formula (II): X 2 X 3 Each can be either hydrogen or halogen.

2. The disperse orange to red 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-5): （I-1） （I-2） （I-3） （I-4） （I-5）。 3. The disperse orange to red 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-3): (II-1) (II-2) (II-3)。 4. The disperse orange to red dye composition according to claim 1, characterized in that: The disperse orange to red dye composition consists of component A and component B.

5. The disperse orange to red dye composition according to claim 4, characterized in that: In the disperse orange to red dye composition, the mass percentage of component A is 10-90%, and the mass percentage of component B is 10-90%.

6. The disperse orange to red dye composition according to claim 1, characterized in that: The disperse orange to red dye composition comprises component A and component B, wherein component A has a mass percentage content of 10-90%, and component B has a mass percentage content of 10-90%, wherein: Component A is selected from at least one of formulas (I-1), (I-2), and (I-3); Component B is selected from at least one of formulas (II-1) and (II-2); （I-1） （I-2） （I-3） (II-1) (II-2)。 7. A disperse orange to red dye product comprising the disperse orange to red dye composition and auxiliaries as described in any one of claims 1-6.

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

1.

9. The disperse orange to red 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, naphthalene sulfonate formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, and sodium lignin sulfonate.

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

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