A preparation method of a dyeing synergist based on modified cardanol for polyester

Abstract

This invention relates to the field of textile auxiliaries, and discloses a method for preparing a dyeing enhancer based on modified cashew nut shell ester for polyester. First, a maleic acid bis-cashew nut shell ester intermediate is prepared by reacting cashew nut shell ester with maleic anhydride. Then, it is compounded with cashew nut shell ester polyoxyethylene ether and polyethylene glycol oleate to obtain the polyester dyeing enhancer. The polyester dyeing enhancer prepared by this invention can improve the dispersibility, retarding properties, and migration properties of disperse dyes, effectively solving the problems of uneven color and dyeing caused by excessively rapid heating in actual processes.

Description

Technical Field

[0001] The invention relates to the field of textile auxiliaries, and in particular to a method for preparing a dyeing synergist based on modified cardanol for polyester. Background Art

[0002] Cardanol is a plant polyphenol extracted from natural cashew nut shell oil. As a bio-based raw material, cardanol can replace or partially replace phenol to make epoxy curing agent, liquid phenolic resin, liquid or powdered thermosetting phenolic resin. In addition, many researchers have modified it and widely used it in the field of surfactants. Existing research data show that non-ionic cardanol polyoxyethylene ether surfactants can be prepared by reacting cardanol with ethylene oxide; cardanol sulfonate surfactants can be prepared by reacting aminosulfonic acid with cardanol; and cardanol carboxylate surfactants can be prepared by reacting maleic anhydride with cardanol. These types of surfactants can be used as industrial cleaning agents, dispersants or fabric leveling agents.

[0003] In the field of textile auxiliaries, the benzene ring and long-chain olefins in the structure of cardanol can be adsorbed on polyester fibers. At the same time, the structure also has a certain affinity for disperse dyes. However, due to the lack of ester groups in the structure, there is still a big difference between its structure and the structure of polyester. It is precisely this difference that limits its synergistic effect in polyester dyeing.

[0004] In the prior art, CN109056371A discloses a disperse dye color fringing preventer, which mainly adopts a disperse component and a transfer component to improve the dyeing uniformity of polyester high-temperature dyeing, wherein the disperse component includes at least one of oleic acid polyoxyethylene ester, coconut oil polyoxyethylene ester, castor oil polyoxyethylene ether, and cardanol polyoxyethylene ether; and the transfer component includes at least one of benzyl cinnamate, benzyl salicylate, diethylene glycol disalicylate, and dibenzyl maleate. Therefore, there is no report on improving the dyeing effect of polyester by using cardanol ester and cardanol polyoxyethylene ether. Summary of the invention

[0005] The technical problem to be solved by the present invention is to overcome the defects of the above-mentioned prior art and provide a preparation method of a dyeing enhancer based on modified cardanol for polyester.

[0006] In order to achieve the above object, the present invention adopts the following technical solutions:

[0007] A: According to the mass ratio, 600-610 parts of cardanol and 95-105 parts of maleic anhydride are added to the reaction container, stirring is started, the temperature is raised to 90-100°C, and the reaction is kept at this temperature for 3-5 hours, and then 5-10 parts of p-toluenesulfonic acid are added to the reaction container, the vacuum is turned on, and the reaction is kept at a vacuum degree of -0.08MPa to -0.095MPa and a temperature of 90-100°C for 2-4 hours to obtain maleic acid biscardanol ester, and the reaction path is as follows:

[0008] Where n=0, 2, 4, 6.

[0009] B: Add 5-15 parts of cardanol maleate, 20-35 parts of cardanol polyoxyethylene ether, 15-35 parts of polyethylene glycol oleate, and 10-25 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well, then slowly add 10-25 parts of deionized water, stir well to obtain a dyeing synergist.

[0010] Preferably, the number of ethylene oxide (EO) segments in the cardanol polyoxyethylene ether structure is 5 to 12. Preferably, the polyethylene glycol oleate is one of polyethylene glycol monooleate and polyethylene glycol dioleate.

[0011] Furthermore, the polyethylene glycol in the polyethylene glycol oleate is PEG400 or PEG600.

[0012] The solvent is one of isopropanol, ethylene glycol monobutyl ether and diethylene glycol monobutyl ether.

[0013] Due to the application of the above technical solution, the present invention has the following advantages:

[0014] The present invention adopts bio-based cardanol as raw material to prepare maleic acid biscardanol ester, and the diester group, double benzene ring and double long-chain olefin structure of the structure have stronger affinity than cardanol. It is applied to polyester disperse dyeing, and the diester structure has a stronger adsorption effect on polyester, can improve the slow dyeing property of disperse dyes, and effectively solves the color flower problem caused by too fast heating in the actual process. At the same time, maleic acid biscardanol ester has a certain plasticizing effect on polyester fiber, reduces the glass transition temperature of polyester during dyeing, improves the swelling property of fiber, strengthens the molecular chain movement in the amorphous region of fiber, promotes the diffusion of dyes into the interior of fiber, and improves the dyeing rate and color fastness; Furthermore, the composite synergistic system formed by maleic acid biscardanol ester, cardanol polyoxyethylene ether and polyethylene glycol oleate can reduce the aggregation of disperse dyes, solubilize and disperse the already aggregated dyes, and re-dye, so as to achieve the purpose of color repair and level dyeing. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1It is the infrared spectrum of biscardanol maleate in the patent of the present invention. Implementation

[0016] The present invention is further described below through specific implementation modes. Example 1

[0017] A: Add 600 parts of cardanol and 100 parts of maleic anhydride into a reaction vessel in proportion by mass, start stirring, heat to 95°C, and keep warm at this temperature for 3 hours, then add 5 parts of p-toluenesulfonic acid into the reaction vessel, start vacuum, keep warm at a vacuum degree of -0.095MPa and a temperature of 100°C for 4 hours to obtain biscardanol maleate.

[0018] B: Add 10 parts of cardanol maleate, 30 parts of cardanol polyoxyethylene ether, 30 parts of polyethylene glycol oleate and 15 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well and then slowly add 15 parts of deionized water, stir well to obtain a dyeing enhancer. Example 2

[0019] A: Add 610 parts of cardanol and 95 parts of maleic anhydride into a reaction vessel in proportion by mass, start stirring, heat to 100°C, and keep the reaction at this temperature for 3 hours, then add 5 parts of p-toluenesulfonic acid into the reaction vessel, start vacuum, keep the reaction at a vacuum degree of -0.095MPa and a temperature of 100°C for 4 hours to obtain biscardanol maleate.

[0020] B: Add 15 parts of cardanol maleate, 25 parts of cardanol polyoxyethylene ether, 30 parts of polyethylene glycol oleate and 20 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well and then slowly add 10 parts of deionized water, stir well to obtain a dyeing enhancer. Example 3

[0021] A: Add 600 parts of cardanol and 95 parts of maleic anhydride into a reaction vessel in proportion by mass, start stirring, heat to 90°C, and keep the reaction at this temperature for 3 hours. Then add 5 parts of p-toluenesulfonic acid into the reaction vessel, start vacuum, keep the reaction at a vacuum degree of -0.095MPa and a temperature of 100°C for 4 hours to obtain biscardanol maleate.

[0022] B: Add 15 parts of cardanol maleate, 30 parts of cardanol polyoxyethylene ether, 25 parts of polyethylene glycol oleate and 15 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well and then slowly add 15 parts of deionized water, stir well to obtain a dyeing enhancer.

[0023] Comparative Example 1

[0024] Add 35 parts of cardanol polyoxyethylene ether, 35 parts of polyethylene glycol oleate and 15 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well and then slowly add 15 parts of deionized water and stir well.

[0025] Application evaluation process:

[0026] Low temperature dyeability

[0027] Disperse Red F3BS 2.0%

[0028] Dye bath pH 4.5~5

[0029] Dyeing enhancer dosage: 0.25g / L

[0030] Bath ratio 1:10

[0031] Heating rate: 2.0℃ / min

[0032] Dyeing temperature 100~130℃

[0033] Dyeing time 30min

[0034] The above dyeing process was used to test the color depth (K / S value) at 100°C, 110°C, 120°C, and 130°C. The blank control was without adding synergist. The experimental results are shown in Table 1.

[0035] Table 1 Comparison of low temperature dyeability results

[0036]

[0037] Transferability

[0038] The migration test was carried out in accordance with the industry standard HG / T4263-2011 "Determination of migration properties of textile dyeing and finishing auxiliaries and polyester leveling agents". The blank control was without adding synergist. The results are shown in Table 2.

[0039] Table 2 Comparison of migration test results

[0040]

[0041] 3. Slow-dyeing

[0042] The slow dyeing property was tested according to the industry standard HG / T4262-2011 "Determination of slow dyeing property of textile dyeing and finishing auxiliaries and polyester leveling agents". The blank control was tested without adding synergist. The results are shown in Table 3.

[0043] Table 3 Comparison of slow-dyeing test results

[0044]

[0045] Combining the results in Tables 1 to 3, it can be seen that the dyeing enhancer of the embodiment of the present invention has a better low-temperature dyeing effect. Compared with the comparative example, the slow dyeing property and the dye migration property are improved.

[0046] 4. Color fastness

[0047] The effect of modified cardanol-based dyeing enhancers for polyester on color fastness is shown in Table 4

[0048] Table 4 Effect of polyester dyeing synergist on dyeing fastness

[0049]

[0050] From the results in Table 4, it can be seen that after the dyeing synergist of the embodiment of the present invention is added to the dye bath, it has little effect on the rubbing fastness and soaping fastness of the fabric dyeing, indicating that the synergist has no adverse effect on the dye fastness.

[0051] 5. Infrared spectroscopy analysis

[0052] Figure 1 Medium 3008cm -1 and 1408cm -1 The characteristic absorption peak of unsaturated olefins is 2923 cm -1 and 2853cm -1 The characteristic absorption peaks of methyl and methylene are at 1730cm -1 The new absorption peak at 3334cm -1 The characteristic peak of the hydroxyl group disappeared, indicating that the phenolic hydroxyl group of cardanol reacted completely with maleic anhydride and the target product was successfully obtained.

[0053] The technical scope of the present invention is not limited to the contents in the above description. Those skilled in the art can make various deformations and modifications to the above embodiments without departing from the technical concept of the present invention, and these deformations and modifications should all fall within the scope of the present invention.

Claims

1. A method for preparing a dyeing synergist based on modified cardanol for polyester, characterized in that The steps include: A: According to the mass ratio, 600-610 parts of cardanol and 95-105 parts of maleic anhydride are added to the reaction vessel, stirring is started, the temperature is raised to 90-100°C, and the reaction is kept at this temperature for 3-5 hours, and then 5-10 parts of p-toluenesulfonic acid are added to the reaction vessel, and the vacuum is turned on. At a vacuum degree of -0.08MPa to -0.095MPa and a temperature of 90-100°C, the reaction is kept at this temperature for 2-4 hours to obtain maleic acid biscardanol ester, the general structure of which is shown as follows: Where n = 0, 2, 4, 6 B: Add 5 to 15 parts of bis-cardanol maleate, 20 to 35 parts of cardanol polyoxyethylene ether, 15 to 35 parts of polyethylene glycol oleate, and 10 to 25 parts of solvent into a reaction vessel equipped with a condensation reflux device, start stirring, mix well, then slowly add 10 to 25 parts of deionized water, stir well to obtain a dyeing synergist.

2. The method for preparing a dyeing synergist based on modified cardanol for polyester according to claim 1, characterized in that: The number of ethylene oxide (EO) segments in the cardanol polyoxyethylene ether structure is 5 to 12, the polyethylene glycol oleate is one of polyethylene glycol monooleate and polyethylene glycol dioleate, and the solvent is one of isopropanol, ethylene glycol monobutyl ether and diethylene glycol monobutyl ether.

3. The method for preparing a dyeing synergist based on modified cardanol for polyester according to claim 2, characterized in that: The polyethylene glycol in the polyethylene glycol oleate is PEG400 or PEG600.

4. A dyeing synergist based on modified cardanol for polyester, characterized in that: The method is obtained by the preparation method according to any one of claims 1 to 3.

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