Golden yellow dye and synthetic method thereof

Abstract

The invention relates to the technical field of textile printing and dyeing, and particularly discloses a golden yellow dye and a synthesis method thereof. According to the golden yellow dye provided by the invention, the structure of each group of the dye is stable and not twisted under the induction of low-energy light waves through the arrangement of the whole structure, excellent color stability is obtained, and the golden yellow dye has non-photosensitivity and excellent low affinity so as to show excellent soaking-resistant soap water fastness; the dye can be effectively used as a non-photosensitive dye to be applied to outdoor or anti-solarization brocade / spandex fabrics.

Description

Technical Field

[0001] The present application relates to the technical field of textile printing and dyeing, and more specifically, to a golden yellow dye and a synthesis method thereof. Background Art

[0002] Photochromism refers to the phenomenon that certain substances change color when exposed to ultraviolet or visible light, and then reversibly return to their original color when the light disappears. It is also called "photochromism" or "photosensitive colorism".

[0003] The principle of photochromic change is that compound A changes its structure or electronic energy level under the stimulation of external light (hv), forming compound B with a different absorption spectrum, and B returns to compound A under the action of light (hv) of other wavelengths or heat. Since the absorption spectrum between the two substances changes, when this change is in the visible light field, a reversible color change similar to the color development and color elimination of human eyes is produced, which is the phenomenon of photochromic change.

[0004] For dyes, the photochromic phenomenon will cause the instability of color light, which brings difficulties to color matching and production. Photochromic dyes are easily affected by environmental factors such as temperature, light, pH value and oxygen, resulting in oxidative deterioration and poor fatigue resistance, which limits their application in textile processing. At the same time, dyes with low affinity are not easy to fall off during soap washing and can maintain good color fastness.

[0005] Among textiles, nylon-spandex fabrics have very high wear resistance, which is 10 times higher than cotton and 20 times higher than wool. Nylon-spandex fabrics are also very elastic. When stretched to 3-6%, the elastic recovery rate can reach 100%, and they can withstand tens of thousands of folds without breaking. Nylon-spandex fabrics are also self-extinguishing, non-toxic, odorless, and have good weather resistance. They are inert to biological erosion and have good antibacterial and anti-mildew capabilities. Therefore, nylon-spandex fabrics are suitable for making windbreakers, down jackets, mountaineering clothes and other clothing that require high strength and wear resistance.

[0006] In summary, a non-photosensitive low-affinity dye is provided which can be effectively used for outdoor or sun-resistant nylon-spandex fabrics. Summary of the invention

[0007] In order to obtain a non-photosensitive dye for nylon-spandex fabrics, which has excellent low affinity and exhibits excellent fastness to soap water, the present application provides a golden yellow dye and a synthesis method thereof.

[0008] In the first aspect, the present application provides a golden yellow dye, which adopts the following technical solution: A golden yellow dye, the specific structural formula of which is:

[0009] In a second aspect, the present application provides a method for preparing a golden yellow dye, using the following technical solution: A method for preparing a golden yellow dye comprises the following preparation steps: S1, dissolving p-phenylenediamine o-sulfonic acid in ice water, adding aqueous hydrochloric acid solution and stirring to mix, then adding NaNO2 solution thereto and stirring to mix, and destroying the excess NaNO2 with sulfamic acid to obtain a diazotized solution; S2, adding 254 ketone to ice water and mixing, then adding the solution to the diazotization solution, adding sodium carbonate to adjust the pH to 3-4, and stirring to obtain a coupling solution; S3, adding PBE to water, adding ice to cool to 0 degrees, adjusting the pH to 3.5-4.5 with NaOH, then adding MCT and water, and adding NaOH to maintain the pH at 2.5-3.5 to obtain a primary condensation product; S4, adding the primary condensation solution to the coupling solution, stirring continuously, heating the reaction, adjusting the pH to 6-7 with NaHCO3 during the process, and finally using membrane salting out and drying to obtain the product, i.e., golden yellow dye; The reaction scheme of the above-mentioned preparation steps is as follows:

[0010] Preferably, the specific steps of S1 are as follows: Dissolve 18.8 g of p-phenylenediamine o-sulfonic acid in 500 mL of ice water, add 26 mL of 30% hydrochloric acid aqueous solution and stir to mix, then add 70 mL of 10% NaNO2 solution and stir to mix, destroy the excess NaNO2 with aminosulfonic acid to obtain a diazotization solution.

[0011] Preferably, the specific steps of S2 are as follows: 32.3 g of 254 ketone was added to 400 mL of ice water and mixed, and then the solution was added to the diazotization solution. Sodium carbonate was added to adjust the pH to 3-4, and the mixture was stirred to obtain a coupling solution.

[0012] Preferably, the specific steps of S3 are as follows: Take 28 g of PBE and add it to 100 mL of water, then add ice to cool to 0 degrees, adjust the pH to 3.5-4.5 with NaOH, then add 18.4 g of MCT and 100 mL of water, and add NaOH to maintain the pH at 2.5-3.5 to obtain a primary condensation product.

[0013] Preferably, the specific steps of S4 are as follows: The primary condensation solution was added to the coupling solution, and the mixture was stirred continuously. The temperature was raised to 50°C and the reaction was carried out for 2 hours. During the reaction, the pH value was adjusted to 6-7 with NaHCO3. Finally, the product was dried by membrane salting out and dried to obtain the golden yellow dye.

[0014] In a third aspect, the present application provides a golden yellow dye and / or the use of a golden yellow dye prepared by any of the above-mentioned synthesis methods in the dyeing process of nylon-spandex fabrics.

[0015] In a fourth aspect, the present application provides a dyeing process, which adopts the following technical solution: A dyeing process comprises the following steps: 1) providing a dye bath comprising the golden yellow dye according to claim 1 and / or the golden yellow dye prepared by the synthesis method according to any one of claims 2 to 6; 2) Immerse the nylon-spandex fabric into the dye bath in 1) at a bath ratio of 1:20 at a constant temperature of 40±2℃; 3) After heating to 75°C and keeping warm for 20 minutes, add 5g / L calcium chloride, continue to heat to 98°C and keep warm for 60 minutes, then wash with water, fix the color, place in 2g / L sodium carbonate at 60°C for 20 minutes, wash with water again, and dry at 70°C to complete the dyeing.

[0016] Preferably, in the nylon-spandex fabric used in step 2), the ratio of nylon to spandex is 71:29.

[0017] Preferably, the usage of the golden yellow dye relative to the nylon-spandex fabric is 1.0% owf.

[0018] In summary, this application has the following beneficial effects: 1. The golden yellow dye obtained in the present application has a stable structure and does not twist under the induction of low-energy light waves through the entire structural arrangement, thereby obtaining excellent color stability, so that it can be effectively used as a non-photosensitive dye for outdoor or sun-resistant nylon-spandex fabrics; In addition, because it is the yellow component of the three primary colors, it can take into account both good dyeing performance and economic performance, which significantly broadens its application and market value.

[0019] 2. The golden yellow dye obtained in the present application is non-photosensitive and has excellent low affinity and exhibits excellent fastness to soap water. It is suitable for dyeing nylon-spandex fabrics, especially nylon-spandex (71:29) fabrics.

[0020] 3. This application optimizes the conditions and steps of the synthesis to a great extent, and the purity and yield of the obtained product are high, and there are basically no by-products, which is conducive to large-scale production and has high industrial value. The synthesis process also has the advantages of high efficiency, low pollution and low emissions. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Figure 1 It is a dyeing process flow chart in this application. DETAILED DESCRIPTION

[0022] The present application is further described in detail below with reference to the accompanying drawings and embodiments. Example

[0023] Example 1 A golden yellow dye, the specific structural formula of which is: And it is prepared by the synthetic method of the following steps: S1, 18.8g of p-phenylenediamine o-sulfonic acid was dissolved in 500mL of ice water, 26mL of 30% hydrochloric acid solution was added and stirred, 70mL of 10% NaNO2 solution was added and stirred, and excess NaNO2 was destroyed with aminosulfonic acid to obtain a diazotized solution; S2, add 32.3 g of 254 ketone into 400 mL of ice water and mix, then add the solution into the diazotization solution, add sodium carbonate to adjust the pH to 3.5, and stir to obtain a coupling solution; S3, add 28 g of PBE to 100 mL of water, add ice to cool to 0 degrees, adjust the pH to 4 with NaOH, add 18.4 g of MCT and 100 mL of water, and add NaOH to maintain the pH at 3 to obtain a primary condensation product; S4. Add the primary condensation solution to the coupling solution, continue stirring, raise the temperature to 50°C and react for 2 hours. During the process, adjust the pH to 6.5 with NaHCO3. Finally, use membrane salting out and drying to obtain the product, i.e., golden yellow dye. The purity is 93.7% after analysis.

[0024] The reaction scheme of the above-mentioned preparation steps is as follows:

[0025] Comparative Example Comparative Example 1 A golden yellow dye, which is different from Example 1 in that the structural formula is as follows:

[0026] Performance testing First, the golden yellow dyes prepared in the embodiments and comparative examples are selected as test objects for standby use, and then their ratings and color differences (D65 10-DL* / Da* / Db* / DE*) are tested respectively after dyeing according to the following specific dyeing method to evaluate their photosensitivity and soap water fastness. The specific dyeing method and detection steps and conditions are as follows: The fabric to be dyed is specifically nylon-spandex fabric (71:29), that is, the ratio of nylon to spandex in the nylon-spandex fabric is 71:29; the dyeing method is as follows: Figure 1 The specific steps are as follows: 1) providing a dye bath of golden yellow dye comprising the golden yellow dye as claimed in claim 1, wherein the amount of the golden yellow dye relative to the nylon-spandex fabric is 1.0% owf; 2) Immerse the nylon-spandex fabric in the dye bath prepared in 1) at a bath ratio of 1:20 at a constant temperature of 40±2°C, wherein 1.0% owf Farman SET-N and HAC+NaAC are added to the dye bath to adjust the pH to 4.5; 3) After heating to 75°C and keeping warm for 20 minutes, add 5g / L calcium chloride, continue to heat to 98°C and keep warm for 60 minutes, then wash with water, fix the color (dye dosage 50% Farman solid FA + 0.15g / L liquid alkali, adjust the pH to 11, keep warm at 60°C for 20 minutes), place it in 2g / L soda ash at 60°C for 20 minutes, wash it with water again, and dry it at 70°C to complete the dyeing.

[0027] After the above operations were performed using the golden yellow dye in Example 1 and the comparative example, the dyed fabrics obtained were recorded as test sample 1 and control sample 1, respectively, and then photosensitivity test and soap water fastness test were performed, and the specific methods were as follows: Photosensitivity test: 1. Place the dyed fabric sample in a dark place overnight and measure the color. The color measurement data is used as the standard value.

[0028] 2. After color measurement, place the fabric sample in a light box (all lights on), and measure the color again after 5min, 10min, 20min, 30min, 45min, and 60min, and compare the color intensity with the standard value.

[0029] 3. To ensure that the position of the fabric sample is the same each time the color is measured, and to minimize the color measurement error, Soap water fastness test: 2g / L washing powder, bath ratio 1:50, pour into the cuvette to prepare the solution, put the fabric in at 70℃ / 98℃ and cool naturally for 15min, stir twice during the period, take out the fabric and observe the color of the remaining water in the cuvette.

[0030] Finally, the Datacolor 1000 colorimeter photosensitivity test software and visual inspection were used to test its rating and color difference (D6510-DL* / Da* / Db* / DE*), and then used to evaluate the photosensitivity and soap water fastness.

[0031] The golden yellow dyes in the above-mentioned Example 1 and Comparative Example 1 were extracted to test the color difference (D65 10-CIE DE) of the fabric to be dyed at a concentration of 1.0% owf, and the test results were recorded in the following table.

[0032] Table 1: Photosensitivity test results of Example 1 and Comparative Example 1 Combining Example 1 and Comparative Example 1 and Table 2, it can be seen that after the golden yellow dye obtained in Example 1 is dyed on nylon-spandex fabric (71:29), and the amount of the golden yellow dye relative to the nylon-spandex fabric is 1.0% owf, the CIE DE value obtained by the above-mentioned photosensitivity test does not exceed 0.1 under the color difference -1.0% D6510 conditions of 5min, 10min, 15min, 20min, 25min, and 30min; while the values ​​of Comparative Example 1 are basically all above 0.2, and the highest reaches 0.4; it can be seen that the golden yellow dye obtained in the present application has a stable structure and does not twist under the induction of low-energy light waves through the entire structural arrangement, thereby obtaining excellent color stability, so that it can be effectively used as a non-photosensitive dye for outdoor or sun-resistant nylon-spandex fabrics. In contrast, Comparative Example 1 with a very similar main structure still does not have the corresponding color stability.

[0033] Table 2: Soap water fastness test results of Example 1 and Comparative Example 1 Combining Example 1 and Comparative Example 1 and Table 2, it can be seen that under the soaking conditions of "70°C + 2g / L washing powder, soaking in water for 15min" and "98°C + 2g / L washing powder, soaking in water for 15min; bath ratio 1:50", the dyed fabrics obtained by Example 1 did not fade, while the color of Comparative Example 1 was clearly visible; it can be seen that the golden yellow dye obtained in the present application not only has excellent non-photosensitivity, but also has excellent low affinity and exhibits excellent fastness to soap water, and is suitable for dyeing nylon-spandex fabrics, especially nylon-spandex fabrics (71:29).

[0034] This specific embodiment is merely an explanation of the present application and is not a limitation of the present application. After reading this specification, those skilled in the art may make modifications to the present embodiment without any creative contribution as needed, but such modifications are protected by the patent law as long as they are within the scope of the claims of the present application.

Claims

1. A golden yellow dye, characterized in that Its specific structural formula is:

2. The method for synthesizing the golden yellow dye according to claim 1, characterized in that: The method comprises the following preparation steps: S1, dissolving p-phenylenediamine o-sulfonic acid in ice water, adding aqueous hydrochloric acid solution and stirring to mix, then adding NaNO2 solution thereto and stirring to mix, and destroying the excess NaNO2 with sulfamic acid to obtain a diazotized solution; S2, adding 254 ketone to ice water and mixing, then adding the solution to the diazotization solution, adding sodium carbonate to adjust the pH to 3-4, and stirring to obtain a coupling solution; S3, adding PBE to water, adding ice to cool to 0 degrees, adjusting the pH to 3.5-4.5 with NaOH, then adding MCT and water, and adding NaOH to maintain the pH at 2.5-3.5 to obtain a primary condensation product; S4, adding the primary condensation solution to the coupling solution, stirring continuously, heating the reaction, adjusting the pH to 6-7 with NaHCO3, and finally drying the product by membrane salting out, i.e., golden yellow dye; The reaction scheme of the above-mentioned preparation steps is as follows:

3. The method for synthesizing golden yellow dye according to claim 1, characterized in that: The specific steps of S1 are as follows: Dissolve 18.8 g of p-phenylenediamine o-sulfonic acid in 500 mL of ice water, add 26 mL of 30% hydrochloric acid aqueous solution and stir to mix, then add 70 mL of 10% NaNO2 solution and stir to mix, destroy the excess NaNO2 with aminosulfonic acid to obtain a diazotization solution.

4. The method for synthesizing golden yellow dye according to claim 1, characterized in that: The specific steps of S2 are as follows: 32.3 g of 254 ketone is added to 400 mL of ice water and mixed, then the solution is added to the diazotization solution, sodium carbonate is added to adjust the pH to 3-4, and the mixture is stirred to obtain a coupling solution.

5. The method for synthesizing golden yellow dye according to claim 1, characterized in that: The specific steps of S3 are as follows: Take 28 g of PBE and add it to 100 mL of water, then add ice to cool to 0 degrees, adjust the pH to 3.5-4.5 with NaOH, then add 18.4 g of MCT and 100 mL of water, and add NaOH to maintain the pH at 2.5-3.5 to obtain a primary condensation product.

6. The method for synthesizing golden yellow dye according to claim 1, characterized in that: The specific steps of S4 are as follows: The primary condensation solution was added to the coupling solution, and the mixture was stirred continuously. The temperature was raised to 50°C and the reaction was carried out for 2 hours. During the reaction, the pH value was adjusted to 6-7 with NaHCO3. Finally, the product was dried by membrane salting out and dried to obtain the golden yellow dye.

7. Use of the golden yellow dye according to claim 1 and / or the golden yellow dye prepared by the synthesis method according to any one of claims 2 to 6 in the dyeing process of nylon-spandex fabrics.

8. A dyeing process, characterized in that: The following steps are involved: 1) providing a dye bath comprising the golden yellow dye according to claim 1 and / or the golden yellow dye prepared by the synthesis method according to any one of claims 2 to 6; 2) Immerse the nylon-spandex fabric in the dye bath in 1) at a bath ratio of 1:20 at a constant temperature of 40±2℃; 3) After heating to 75°C and keeping warm for 20 minutes, add 5g / L calcium chloride, continue to heat to 98°C and keep warm for 60 minutes, then wash with water, fix the color, place in 2g / L sodium carbonate at 60°C for 20 minutes, wash with water again, and dry at 70°C to complete the dyeing.

9. The dyeing process according to claim 8, characterized in that: In the nylon-spandex fabric used in step 2), the ratio of nylon to spandex is 71:

29.

10. The dyeing process according to claim 8, characterized in that: The usage of the golden yellow dye relative to the nylon-spandex fabric is 1.0% owf.

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