Turquoise blue disperse dye for supercritical CO2 dyeing, preparation method of turquoise blue disperse dye and polyester fiber product

Abstract

The invention provides a turquoise blue disperse dye for supercritical CO2 dyeing, a preparation method of the turquoise blue disperse dye and a polyester fiber product, and particularly relates to the technical field of dye chemical industry. The turquoise blue disperse dye for supercritical CO2 dyeing has the following structure: # imgabs0 #. Wherein R1 is an alkylene group with 1 to 8 carbon atoms, R2 is an alkylene group with 1 to 8 carbon atoms, and R3 is an alkyl group with 1 to 8 carbon atoms. The turquoise blue disperse dye for supercritical CO2 dyeing provided by the invention shows an excellent dyeing effect in a supercritical CO2 dyeing system, and the dye uptake of the turquoise blue disperse dye can reach 80% or above; various color fastness (including washing fastness, rubbing fastness, light fastness and the like) and physical performance indexes of fabric textiles dyed by the dye through supercritical CO2 can meet the standard requirements of a traditional aqueous medium dyeing process. In addition, the turquoise blue disperse dye disclosed by the invention has good application flexibility and can meet the dyeing requirements of different color systems.

Description

Technical Field

[0001] The present invention relates to the technical field of dye chemical industry, in particular to a method for using supercritical CO 2 A turquoise blue disperse dye for dyeing, a preparation method thereof and a polyester fiber product. Background Art

[0002] Implementing low-carbon resource consumption, clean production and resource recycling in the textile industry to reduce or even eliminate pollution to water bodies and the atmospheric environment has become the main direction of technological progress in the industry. 2 As a typical green technology, waterless dyeing technology is one of the important ways to achieve green and sustainable development of the textile printing and dyeing industry. Vigorously developing and promoting this technology has important economic, social and environmental significance.

[0003] Supercritical CO 2 Dyeing technology is one of the most popular waterless dyeing technologies. Its principle is that when the temperature and pressure reach CO 2 At the critical point, CO 2 It will become a uniform fluid medium that can dissolve dispersed dyes and transfer the energy it obtains from the outside world to the dyes and the dyed fibers, providing energy guarantee for the dyeing, diffusion and adhesion of the dyes on the fibers. This technology can achieve zero wastewater discharge during the dyeing process. After dyeing is completed, the dyes and CO 2 It can be recycled, and the dyed fabric is in a dry state, without the need for drying. This is not only effective in energy saving, emission reduction, and consumption reduction, but also environmentally friendly, thus promoting sustainable development of environmental protection.

[0004] In recent years, with the development of supercritical CO 2 Continuous innovation and development of dyeing equipment and dyeing technology, supercritical CO 2 Dyeing technology has been gradually applied to large-scale, industrialized production. However, there is currently no mature and stable disperse dye suitable for this technology on the market, especially bright and beautiful turquoise disperse dyes. Common brightly colored disperse blue dyes on the market, such as CI Disperse Blue 284, CI Disperse Blue 354 and CI Disperse Blue 60, are used in supercritical CO 2 After dyeing with dyeing technology, the dyeing rate is extremely low, only about 20%~40%, and the effect is extremely unsatisfactory. Therefore, the market urgently needs a method that can be used in supercritical CO 2 The turquoise blue disperse dyes used for dyeing are used to meet the needs of industry development.

[0005] In view of this, the present invention is proposed. Summary of the invention

[0006] One of the objects of the present invention is to provide a method for supercritical CO 2The turquoise blue disperse dyes are used to fill the market gap and solve the problem that the existing brilliant blue and turquoise blue disperse dyes are not suitable for supercritical CO 2 In order to solve the problem of dyeing technology, a turquoise disperse dye with special structure and bright color is provided.

[0007] The second object of the present invention is to provide a supercritical CO 2 The invention discloses a method for preparing turquoise blue disperse dye for dyeing.

[0008] A third object of the present invention is to provide a polyester fiber product.

[0009] In order to achieve the above-mentioned purpose of the present invention, the following technical solutions are particularly adopted: In a first aspect, the present invention provides a method for supercritical CO 2 The turquoise blue disperse dye for dyeing has the structure shown in formula I: Formula I; Among them, R 1 is a C1-C8 alkylene group, R 2 is a C1-C8 alkylene group, R 3 It is a C1-C8 alkyl group.

[0010] Furthermore, R 1 is a C1-C4 alkylene group, R 2 is a C1-C4 alkylene group, R 3 It is a C1-C4 alkyl group.

[0011] Furthermore, R 1 is selected from ethylene or propylene; R 2 is selected from methylene or ethylene; R 3 Selected from methyl or ethyl.

[0012] The second aspect of the present invention provides a method for preparing the turquoise blue disperse dye, wherein 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride is subjected to a condensation reaction with compound 1 in the absence of a solvent to obtain the turquoise blue disperse dye; Among them, the structural formula of compound 1 is NH 2 R 1 OR 2 OR 3 , R 1 is a C1-C8 alkylene group, R 2 is a C1-C8 alkylene group, R 3 It is a C1-C8 alkyl group.

[0013] Furthermore, R 1 is a C1-C4 alkylene group, R 2 is a C1-C4 alkylene group, R 3It is a C1-C4 alkyl group.

[0014] Furthermore, R 1 is selected from ethylene or propylene; R 2 is selected from methylene or ethylene; R 3 Selected from methyl or ethyl.

[0015] Furthermore, the mass volume ratio of the 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride to the compound 1 is 1:(5-15), preferably 1:(10-15).

[0016] Furthermore, the temperature of the condensation reaction is 0-100°C, preferably 25-70°C.

[0017] Preferably, the condensation reaction time is 2 to 10 hours, preferably 3 to 5 hours.

[0018] The third aspect of the present invention provides a polyester fiber product, which is prepared by using the turquoise blue disperse dye in a supercritical CO 2 The dyeing method is dyed.

[0019] Furthermore, the polyester fiber is polyethylene terephthalate fiber.

[0020] Compared with the prior art, the present invention has at least the following beneficial effects: The invention provides a method for supercritical CO 2 Dyeing of turquoise blue disperse dye in supercritical CO 2 The dyeing system shows excellent dyeing effect, and its dyeing rate can reach more than 80%, which is significantly better than the dyeing rate of 20-40% of similar dyes in the prior art. 2 The dyed fabrics and textiles have various color fastnesses (including washing fastness, rubbing fastness, sunlight fastness, etc.) and physical performance indicators that can meet the standard requirements of traditional water-based dyeing processes. In addition, the turquoise blue disperse dye of the present invention has good application flexibility and can be used independently as a single dye or combined with other dyes suitable for supercritical CO 2 The disperse dyes of dyeing technology can be used in combination to meet the dyeing needs of different color systems. This excellent compatibility makes it have a wider application prospect in actual production.

[0021] The preparation method provided by the present invention adopts a solvent-free synthesis process, avoids the use of organic solvents in the preparation of traditional dyes, reduces the emission of volatile organic compounds (VOCs) from the source, and conforms to the development concept of green chemistry. At the same time, the reaction conditions are mild, the product yield is high, and there are few by-products, which is easy to purify and suitable for large-scale industrial production.

[0022] The polyester fiber product provided by the present invention has excellent dyeing effect, environmental protection characteristics and practical performance, and provides an efficient, clean and high-quality dyeing solution for the textile industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0024] Figure 1 is the supercritical CO in Experimental Example 1 2 Dyeing process route. DETAILED DESCRIPTION

[0025] The embodiments of the present invention will be described in detail below in conjunction with the embodiments and examples, but those skilled in the art will understand that the following embodiments and examples are only used to illustrate the present invention and should not be considered to limit the scope of the present invention. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0026] In a first aspect, the present invention provides a method for supercritical CO 2 The turquoise blue disperse dye for dyeing has the structure shown in formula I: Formula I; Among them, R 1 is a C1-C8 alkylene group, R 2 is a C1-C8 alkylene group, R 3 It is a C1-C8 alkyl group.

[0027] The invention provides a method for supercritical CO 2 Dyeing of turquoise blue disperse dye in supercritical CO 2 The dyeing system shows excellent dyeing effect, and its dyeing rate can reach more than 80%, which is significantly better than the dyeing rate of 20-40% of similar dyes in the prior art. 2 The dyed fabrics and textiles have various color fastnesses (including washing fastness, rubbing fastness, sunlight fastness, etc.) and physical performance indicators that can meet the standard requirements of traditional water-based dyeing processes. In addition, the turquoise blue disperse dye of the present invention has good application flexibility and can be used independently as a single dye or combined with other dyes suitable for supercritical CO 2The disperse dyes of dyeing technology can be used in combination to meet the dyeing needs of different color systems. This excellent compatibility makes it have a wider application prospect in actual production.

[0028] Typical but not limiting, R 1 R may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl; 2 R may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl; 3 It can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl. 1 , R 2 and R 3 Can be the same or different.

[0029] Furthermore, R 1 is a C1-C4 alkylene group, R 2 is a C1-C4 alkylene group, R 3 It is a C1-C4 alkyl group.

[0030] Furthermore, R 1 is selected from ethylene or propylene; R 2 is selected from methylene or ethylene; R 3 Selected from methyl or ethyl.

[0031] The second aspect of the present invention provides a method for preparing the turquoise blue disperse dye, wherein 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride is subjected to a condensation reaction with compound 1 in the absence of a solvent to obtain the turquoise blue disperse dye; Among them, the structural formula of compound 1 is NH 2 R 1 OR 2 OR 3 , R 1 is a C1-C8 alkylene group, R 2 is a C1-C8 alkylene group, R 3 It is a C1-C8 alkyl group.

[0032] The preparation method provided by the present invention adopts a solvent-free synthesis process, avoids the use of organic solvents in the preparation of traditional dyes, reduces the emission of volatile organic compounds (VOCs) from the source, and conforms to the development concept of green chemistry. At the same time, the reaction conditions are mild, the product yield is high, and there are few by-products, which is easy to purify and suitable for large-scale industrial production.

[0033] The reaction formula of the condensation reaction is: .

[0034] Furthermore, R 1 is a C1-C4 alkylene group, R 2 is a C1-C4 alkylene group, R 3 It is a C1-C4 alkyl group.

[0035] Furthermore, R 1 is selected from ethylene or propylene; R 2 is selected from methylene or ethylene; R 3 Selected from methyl or ethyl.

[0036] Furthermore, the mass volume ratio of the 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride to the compound 1 is 1:(5-15), preferably 1:(10-15).

[0037] Typically but not limiting, the mass volume ratio of 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride to compound 1 can be, for example, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14 or 1:15, or any value in the range of 1:5 to 1:15; preferably, the mass volume ratio can be, for example, 1:10, 1:11, 1:12, 1:13, 1:14 or 1:15, or any value in the range of 1:10 to 1:15.

[0038] Furthermore, the temperature of the condensation reaction is 0-100°C, preferably 25-70°C.

[0039] Typically but not limiting, the temperature of the condensation reaction may be, for example, 0°C, 10°C, 20°C, 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C or 100°C, or any value in the range of 0°C to 100°C; preferably, the temperature of the condensation reaction may be, for example, 25°C, 30°C, 40°C, 50°C, 60°C, 70°C, or any value in the range of 25°C to 70°C.

[0040] The progress of the condensation reaction can be monitored by conventional testing methods in the art (such as HPLC), and the reaction endpoint is when the 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride reacts to ≤1%.

[0041] Preferably, the condensation reaction time is 2 to 10 hours, preferably 3 to 5 hours.

[0042] The condensation reaction time may be, for example, 2 h, 3 h, 4 h, 5 h, 6 h, 7 h, 8 h, 9 h or 10 h, or any value within the range of 2 h to 10 h; preferably, the condensation reaction time may be, for example, 3 h, 4 h or 5 h, or any value within the range of 3 h to 5 h.

[0043] The third aspect of the present invention provides a polyester fiber product, which is prepared by using the turquoise blue disperse dye in a supercritical CO 2 The dyeing method is dyed.

[0044] The turquoise blue disperse dye provided by the present invention does not need to add a dispersant when used, and the sanding or grinding treatment steps required in the traditional process are omitted. The prepared product of the compound only needs to be collected by filter cake and conventionally dried, and can be directly applied to supercritical CO 2 Dyeing equipment carries out dyeing operations.

[0045] Furthermore, the polyester fiber is polyethylene terephthalate fiber.

[0046] The polyester fiber product provided by the present invention has excellent dyeing effect, environmental protection characteristics and practical performance, and provides an efficient, clean and high-quality dyeing solution for the textile industry.

[0047] The present invention is further described below by specific examples and comparative examples, but it should be understood that these examples are only used for more detailed description and should not be understood as limiting the present invention in any form. The raw materials used in the examples and comparative examples of the present invention, if no specific conditions are specified, are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used without indicating the manufacturer are all conventional products that can be purchased commercially.

[0048] The LC-MS data described in the present invention are obtained by testing with a Waters UPLC-SQD liquid-mass spectrometer (the mobile phase is an acetonitrile / water system, 60%-90% acetonitrile V / V, and the column temperature is 40°C).

[0049] The supercritical CO 2 The waterless dyeing was completed with the assistance of Qingdao Jifa Group. The supercritical CO 2 The dyeing equipment and technology are all from Qingdao Jifa Group.

[0050] Example 1 This embodiment provides a turquoise blue disperse dye, and the preparation method is as follows: Measure 600 mL of 3-methoxyethoxypropylamine in a dry 1000 mL four-necked flask, then start stirring, slowly add 58.5 g of 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride, stir evenly at room temperature for about 30 minutes, then slowly raise the temperature to 40-45°C. Control the temperature at 40-45°C for 3 hours, take samples for HPLC analysis, and the condensation reaction is completed when the content of 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride is ≤1%.

[0051] Add 100 mL of methanol for separation, stir at 40-45°C for 30 min, cool to below 30°C, filter, wash the filter cake with a small amount of methanol (collect the filtrate to recover methanol and excess 3-methoxyethoxypropylamine for the next batch of experiments), wash the filter cake with hot water until neutral and then dry to obtain turquoise blue disperse dye (R 1 is propylene, R 2 is ethylene, R 3 is methyl).

[0052] The structural formula is shown in Formula I-1 below.

[0053] Formula Ⅰ-1.

[0054] Embodiment 2-8 According to the preparation method of Example 1, the groups in compound 1 were adjusted to obtain a turquoise blue disperse dye of the corresponding structure. The specific experimental data and structure identification data are shown in Table 1.

[0055] Table 1

[0056] Comparative Example 1 This comparative example provides 100g of C.I. Disperse Blue 60 original dye (without dispersant):

[0057] Test Example 1 Take 100g of each disperse dye of the embodiment and comparative example and heat them with supercritical CO 2 The dyeing equipment dyes 5000g of polyester fiber cloth respectively. The specific dyeing process is as follows: Figure 1 As shown, including: 1. Fix the hollow stainless steel shaft with polyester fiber cloth and small holes in the wall into the high-pressure dyeing tank. Then put the dye into the dye tank for use. The liquid carbon dioxide (CO 2 ) After cooling, it is compressed to the set pressure by a booster pump and heated to the preset temperature by a heater to form supercritical CO 2 fluid.

[0058] 2. Supercritical CO2 The fluid enters the dissolution tank, fully contacts the dye and dissolves the dye. Subsequently, the CO 2 The fluid is delivered to the stainless steel shaft inner cylinder of the high pressure dyeing tank. 2 The fluid diffuses outward through the small holes in the drum wall, penetrates the fabric layer and completes the dyeing. To ensure uniform dyeing, the circulation pump continuously increases CO 2 The number of times the fluid is circulated through the system until dyeing is complete.

[0059] 3. After dyeing, CO 2 The fluid enters the separator to release the pressure. As the pressure decreases, CO 2 When the gas is restored, the solubility of the dye decreases, and the dye precipitates and is recovered. 2 The gas is cooled in a cooler and restored to liquid form, and is eventually recovered and stored in a storage tank for recycling.

[0060] The dye uptake rate calculated based on the remaining amount of dye is listed in Table 2.

[0061] Table 2

[0062] As can be seen from Table 2, the turquoise blue disperse dye of the present invention was subjected to supercritical CO 2 After dyeing, the remaining amount of dye is about 20g, and the equivalent dye uptake is about 80%. However, the remaining amount of CI disperse blue 60 original dye (without dispersant) in comparative example 1 is relatively large, and the equivalent dye uptake is only 22.4%. Due to its low dye uptake, the cloth surface also appears light turquoise blue. Its result is far inferior to the disperse dye of the present invention.

[0063] Test Example 2 The dyed fabric sample obtained in Test Example 1 was tested for its color fastness to washing, perspiration, sunlight and sublimation according to ISO 105 C10 C (3), ISO 105 E04, ISO 105 B02 and GB / T 5718-1997. The test results are shown in Table 3.

[0064] Table 3

[0065] As can be seen from the results in Table 3, the turquoise blue disperse dye of the present invention was subjected to supercritical CO 2 The fabrics dyed by the dyeing equipment also have excellent dyeing performance and color fastness.

[0066] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or replace some or all of the technical features therein with equivalents. However, these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A turquoise blue disperse dye for supercritical CO2 dyeing, characterized in that: It has the structure shown in formula I: Formula I; Among them, R1 is a C1-C8 alkylene group, R2 is a C1-C8 alkylene group, and R3 is a C1-C8 alkyl group.

2. The turquoise blue disperse dye according to claim 1, characterized in that R1 is a C1-C4 alkylene group, R2 is a C1-C4 alkylene group, and R3 is a C1-C4 alkyl group.

3. The turquoise blue disperse dye according to claim 1, characterized in that R1 is selected from ethylene or propylene; R2 is selected from methylene or ethylene; R3 is selected from methyl or ethyl.

4. A method for preparing the turquoise blue disperse dye according to any one of claims 1 to 3, characterized in that: In the absence of solvent, 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride is subjected to a condensation reaction with compound 1 to obtain the turquoise blue disperse dye; Wherein, the structural formula of compound 1 is NH2R1OR2OR3, R1 is a C1-C8 alkylene group, R2 is a C1-C8 alkylene group, and R3 is a C1-C8 alkyl group.

5. The preparation method according to claim 4, characterized in that: R1 is a C1-C4 alkylene group, R2 is a C1-C4 alkylene group, and R3 is a C1-C4 alkyl group.

6. The preparation method according to claim 4, characterized in that: R1 is selected from ethylene or propylene; R2 is selected from methylene or ethylene; R3 is selected from methyl or ethyl.

7. The preparation method according to claim 4, characterized in that: The mass volume ratio of the 1,4-diaminoanthraquinone-2,3-dicarboxylic anhydride to the compound 1 is 1:(5-15).

8. The preparation method according to claim 4, characterized in that: The condensation reaction temperature is 0-100° C. and the reaction time is 2-10 hours.

9. A polyester fiber product, characterized in that: The turquoise blue disperse dye according to any one of claims 1 to 3 is used for dyeing according to a supercritical CO2 dyeing method.

10. The polyester fiber product according to claim 9, characterized in that: The polyester fiber is polyethylene terephthalate fiber.

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