Carbene dyes containing bis-isoreactive groups, their synthesis and dyeing applications

Abstract

The present application belongs to the field of fine chemical industry and the field of textile printing and dyeing, and particularly relates to a kind of carbene dyes containing double isoreaction groups and a synthesis method and dyeing application thereof. A new type of carbene dye with double isoreaction groups is designed and developed by simultaneously introducing phenyl trifluoromethyl bisaziridine structure and 2-diazopropandioic acid diester structure into the structure of the dye. The application also simultaneously provides the application of the above-mentioned carbene dye containing double isoreaction groups in polyester fabric dyeing. The present application combines the chemical reaction process of the dye with the dyeing process, saves the operation steps and operation time, saves the energy consumption, and reduces the production cost.

Description

Technical Field

[0001] This invention belongs to the fields of fine chemicals and textile printing and dyeing, specifically relating to a carbene dye containing two different reactive groups, its synthesis method, and its dyeing application. Background Technology

[0002] Carbene dyes are a class of dyes containing carbene precursor structures. Common carbene dyes include bisacrylidine dyes and diazo dyes. Under specific high-temperature conditions, both types of dyes can release nitrogen molecules to form reactive carbene intermediates, which can then react chemically with adjacent nitrogen-hydrogen bonds, oxygen-hydrogen bonds, and even carbon-hydrogen bonds, thereby achieving a strong covalent bond between the dye and synthetic fibers such as polyester. The emergence of carbene dyes provides a new approach to solving the problem of poor heat migration colorfastness in dyed polyester fabrics.

[0003] The literature (Dyes and Pigments, 2021, 194, 109555) indicates that the thermal response temperature (the temperature at which nitrogen molecules begin to be released and carbene intermediates are formed) of carbene dyes based on the phenyltrifluoromethyl bisacrylidine structure is approximately in the range of 120-130℃. When these dyes are ground and then used in an aqueous system for high-temperature, high-pressure dyeing (130℃, 60 min) on polyester fabrics, the dye molecules can react chemically with the fibers while dyeing them, but the fixation rate is generally low, only about 30%-40%. A study (Modern Textile Technology, 2025, 33(7), 74-81) found that bisacrylidine dyes based on nitrothiazole chromophores have a high fixation effect on polyester under the aforementioned dyeing conditions, with a fixation rate reaching 59% (when the dye dosage is 1% owf). Correspondingly, dyed polyester fabrics have excellent color fastness to washing, rubbing and sublimation, and also have good color fastness to dry heat migration. However, in the presence of oily auxiliaries, the color fastness to heat migration of dyed fabrics is still relatively poor.

[0004] Although using dyes containing two diazinon reactive groups can significantly increase the probability of dye reaction with fibers, the phenyltrifluoromethyl diazinon structure itself is relatively large. Introducing two phenyltrifluoromethyl diazinon structures into the dye molecule slows down the dyeing rate on polyester fabrics, resulting in the dye not reacting with the fiber in time and thus reducing the fixation rate of the dyed fabric. This phenomenon has been confirmed in the literature (Dyes and Pigments, 2026, 246, 113416).

[0005] Diazocarbene dyes are characterized by their easily modifiable structure and convenient performance control. Compared to the aforementioned bisacrylidine module, the diazo module is smaller in size. Literature (Dyes and Pigments, 2025, 239, 112755) demonstrates that dyes based on the 2-diazomalonic acid diester structure have a high thermal response temperature (>150℃). Patent (CN119592098) confirms that such carbene dyes, after dyeing using the aforementioned high-temperature and high-pressure method followed by treatment at 180~200℃, can achieve excellent color fixation. However, the migration fastness of polyester fabrics dyed with diazocarbene dyes in the presence of oily auxiliaries, as reported in existing studies, remains relatively poor. Furthermore, 2-diazomalonic acid diester-type carbene dyes cannot achieve effective covalent bonding between the dye and polyester fibers simply by high-temperature and high-pressure dyeing at 130℃. Summary of the Invention

[0006] The technical problem to be solved by the present invention is to provide a disperse dye with high heat migration fastness. To this end, a carbene dye containing two iso-reactive groups is provided, as well as its synthesis method and dyeing application.

[0007] To solve the above-mentioned technical problems, the present invention provides a carbene dye containing two isoreactive groups, the general structural formula of which is as follows:

[0008] ;

[0009] Among them, R 1 and R 2 They are selected from hydrogen atoms, methyl groups, methoxy groups, and acetamido groups, respectively.

[0010] Ar is selected from any of the following structures:

[0011] , , , , , , , , , , , , .

[0012] Note: The molecular structure contains both a phenyltrifluoromethyl bisacrylidine structure and a 2-diazomalonic acid diester structure.

[0013] As an improvement to the carbene dye containing two different reactive groups of the present invention, its structural formula is any one of the following:

[0014]

[0015] II

[0016]

[0017] III

[0018]

[0019] IV

[0020]

[0021] V

[0022]

[0023] VI

[0024]

[0025] VII

[0026]

[0027] VIII

[0028]

[0029] IX

[0030] This invention also provides a method for synthesizing the above-mentioned carbene dye containing two isoreactive groups, comprising the following steps:

[0031] (1) Compound M is condensed with monomethyl malonate to obtain compound N;

[0032] (2) Compound N was condensed with 4-[3-(trifluoromethyl)-3H-bisacryl-3-yl]benzoic acid to obtain compound P;

[0033] (3) Compound P is reacted with a diazo group transfer reaction to obtain compound Q;

[0034] (4) Using compound Q as the coupling component, a coupling reaction is carried out with the corresponding diazonium salt to obtain the target dye (a carbene dye containing two different reactive groups);

[0035] The structural formula of compound M is:

[0036] ,

[0037] The structure of compound N is as follows:

[0038] ,

[0039] The structure of compound P is as follows:

[0040] ,

[0041] The structure of compound Q is as follows:

[0042] ,

[0043] Among them, R 1 and R 2 They are selected from hydrogen atoms, methyl groups, methoxy groups, and acetamido groups, respectively.

[0044] The diazonium salt is any one of the following:

[0045] , , , , , , , , , , , , .

[0046] As an improvement to the synthesis method of the carbene dye containing two different reactive groups of the present invention: compound M is N,N-dihydroxyethylaniline.

[0047] The present invention also provides the application of the above-mentioned carbene dyes containing two different reactive groups in the dyeing of polyester fabrics.

[0048] As an improvement to the application of the present invention, the following steps are included:

[0049] S1. After thoroughly mixing the carbene dye, dispersant, and water, the mixture is milled to obtain a dye dispersion.

[0050] S2. The polyester fabric is dyed using the dispersion obtained in step S1 to obtain a dyed fabric; the dyeing temperature is 130±5℃.

[0051] S3. Perform reduction cleaning on the dyed fabric obtained in step S2 to obtain the final dyed fabric.

[0052] In the process of invention: The original concept of this invention was to simultaneously introduce the phenyltrifluoromethyl bisacrylidine structure and the 2-diazomalonic acid diester structure into the dye molecule to develop a carbene dye with two different reactive groups. The original intention was to utilize the bisacrylidine module to initiate the first chemical reaction between the dye and the fiber during high-temperature, high-pressure dyeing (130°C), and then, after dyeing, use the diazo module to initiate a second chemical reaction between the dye and the fiber through high-temperature treatment (180~200°C), thereby increasing the reaction rate between the dye and the fiber and improving the heat migration fastness of dyed polyester fabrics in the presence of oily auxiliaries. However, unexpectedly, the color fixation rate of the dyed fabric after high-temperature, high-pressure dyeing and subsequent color fixation treatment was not higher than that of the fabric dyed only under high-temperature, high-pressure conditions. Furthermore, this color fixation rate was lower than that of polyester fabric dyed with a carbene dye containing only one bisacrylidine module, indicating that the diazo group in the dye molecule had already undergone transformation during the high-temperature, high-pressure dyeing process. Nevertheless, what is even more surprising is that polyester fabrics dyed with carbene dyes containing dual iso-reactive groups exhibit excellent color fastness grades across the board, particularly in the presence of oily auxiliaries, for heat migration fastness.

[0053] The innovation of this invention lies in:

[0054] 1. Structural Innovation of Carbene Dyes. A novel carbene dye with two isomeric reactive groups was designed and developed by simultaneously introducing phenyltrifluoromethyl bisacrylidine and 2-diazomalonic acid diester structures into the dye structure. When this type of dye is used for dyeing polyester fabrics using a high-temperature, high-pressure dyeing method, the dyed polyester exhibits excellent color fastness across various aspects, particularly excellent heat migration fastness in the presence of oily auxiliaries, thus solving the industry-wide problem of color fading in dyed polyester fabrics due to heat setting in the presence of oily auxiliaries.

[0055] 2. Innovation in the Application of Carbene Dyes. Existing approaches to achieving high colorfastness with carbene dyes focus on enhancing the reactivity between the dye and fiber, thereby achieving a firm bond between the dye and the fiber. Through long-term practice, this invention has discovered that achieving high colorfastness with carbene dyes does not necessarily require a chemical reaction between the dye and fiber. For example, the carbene dye of this invention does not exhibit a high fixation rate on polyester fabrics, but it possesses superior heat migration resistance compared to existing carbene dyes.

[0056] 3. Innovation in Carbene Dyeing Application Methods. Existing carbene dyes often separate the dyeing and reaction processes to achieve high reactivity between the dye and fiber, requiring an additional fixation step after dyeing. This invention utilizes a developed bi-isoreactive carbene dye to achieve high colorfastness in a one-step high-temperature, high-pressure dyeing method. In other words, to achieve high colorfastness, especially high heat migration fastness in the presence of oily auxiliaries, using the bi-isoreactive carbene dye of this invention is essential in conventional high-temperature, high-pressure dyeing methods.

[0057] The advantages of this invention include:

[0058] Existing carbene dyeing methods for polyester typically require an additional fixing step, which involves high fixing temperatures, long fixing times, and high energy consumption. Furthermore, significant dye thermal migration may still occur in dyed polyester fabrics even in the presence of oily auxiliaries. In contrast, this invention integrates the chemical reaction process of the dye with the dyeing process, saving operational steps and time, conserving energy, and reducing production costs. This invention does not alter existing dyeing processes, yet achieves high resistance to thermal migration in dyed polyester fabrics.

[0059] The aforementioned effects are achieved thanks to the creation of the novel carbene dye of this invention. The dye molecule of this invention simultaneously contains a phenyltrifluoromethylbisacrylidine structure and a 2-diazomalonic acid diester structure. Both the bisacrylidine and diazo structures are carbene precursors, which can release nitrogen molecules and generate reactive carbene intermediates at specific temperatures. As a separate study, the thermal response temperature of the phenyltrifluoromethylbisacrylidine structure is approximately 120-130°C, while the thermal response temperature of the 2-diazomalonic acid diester structure is approximately 150°C. The following is a theoretical explanation of the principle of this invention: During high-temperature, high-pressure dyeing, when the temperature reaches approximately 130°C, the bisacrylidine module first transforms to form a carbene intermediate. A small portion of the carbene intermediate reacts chemically with the carbon-hydrogen bonds on adjacent fibers, thereby causing the dye to be firmly bound to the polyester fiber in a covalent bond form. This portion of the dye cannot be extracted by hot N,N-dimethylformamide. Most carbene intermediates trigger a transformation of the diazo group, removing nitrogen molecules to form carbene intermediates, which initiates intramolecular or intermolecular crosslinking reactions in the dye molecules, causing significant changes in the dye structure. These structural changes hinder the migration of dye molecules within polyester fibers. Attached Figure Description

[0060] The specific embodiments of the present invention will be further described in detail below with reference to the accompanying drawings.

[0061] Figure 1 This is the synthetic route for the carbene dye of this invention;

[0062] Figure 2 The 1H NMR spectrum of compound 1;

[0063] Figure 3 The carbon NMR spectrum of compound 1;

[0064] Figure 4 The 1H NMR spectrum of compound 2;

[0065] Figure 5 The carbon NMR spectrum of compound 2;

[0066] Figure 6 The 1H NMR spectrum of compound 3;

[0067] Figure 7 The carbon NMR spectrum of compound 3;

[0068] Figure 8 The 1H NMR spectrum of dye II;

[0069] Figure 9 The NMR carbon spectrum of dye II;

[0070] Figure 10 The 1H NMR spectrum of dye III;

[0071] Figure 11 The nuclear magnetic resonance carbon spectrum of dye III;

[0072] Figure 12 The 1H NMR spectrum of dye IV;

[0073] Figure 13 The NMR carbon spectrum of dye IV;

[0074] Figure 14 UV-Vis absorption spectra of dyes II to IV in DMF;

[0075] Figure 15 Thermogravimetric and differential scanning calorimetric curves for dye II;

[0076] Figure 16 Thermogravimetric and differential scanning calorimetric curves for dye III;

[0077] Figure 17 Thermogravimetric and differential scanning calorimetric curves of dye IV;

[0078] Figure 18 The staining of cotton (middle) and polyester (lower) linings was measured at different temperatures for the heat migration color fastness of dyed fabrics (upper row) dyed with dye II.

[0079] Figure 19The staining of cotton lining (middle row) and polyester lining (lower row) was measured at different temperatures for the heat migration color fastness of fabric samples (upper row) after treatment with oily auxiliaries dyed with dye II.

[0080] Figure 20 The staining of cotton (upper) and polyester (lower) linings on fabrics dyed with dye III (middle row) at different temperatures was measured.

[0081] Figure 21 The staining of cotton lining (upper row) and polyester lining (lower row) at different temperatures was measured for the heat migration color fastness of fabric samples (middle row) after treatment with oily auxiliaries dyed with dye III.

[0082] Figure 22 The staining of cotton (upper) and polyester (lower) linings on fabrics dyed with dye IV (middle row) at different temperatures was measured.

[0083] Figure 23 The staining of cotton (upper) and polyester (lower) linings was measured at different temperatures for the heat migration color fastness of fabric samples (middle row) after treatment with oily auxiliaries dyed with dye IV.

[0084] Figure 24 To compare the color fastness of heat migration of fabrics dyed with dye F1 (middle row) at different temperatures, the staining of cotton lining (upper row) and polyester lining (lower row) was studied.

[0085] Figure 25 To compare the color staining of cotton lining (upper row) and polyester lining (lower row) at different temperatures, the heat migration color fastness of fabric samples (middle row) after treatment with oily auxiliaries was measured with dye F1.

[0086] Figure 26 To compare the color fastness of heat migration of fabrics dyed with dye F2 (middle row) at different temperatures, the staining of cotton lining (upper row) and polyester lining (lower row) was studied.

[0087] Figure 27 To compare the color staining of cotton lining (upper row) and polyester lining (lower row) at different temperatures, the heat migration color fastness of fabric samples (middle row) after treatment with oily auxiliaries was measured with dye F2.

[0088] Figure 28 To compare the color fastness to heat migration of fabrics dyed with dye F3 (upper row) at different temperatures, the staining of cotton lining (middle row) and polyester lining (lower row) was studied.

[0089] Figure 29To compare the staining of cotton lining (upper row) and polyester lining (lower row) at different temperatures, the heat migration color fastness of fabric samples (middle row) after treatment with oily auxiliaries was measured with dye F3.

[0090] Figure 30 The staining of cotton (upper) and polyester (lower) linings was measured at different temperatures for the heat migration fastness of dye IV-dyed fabrics (without reduction washing) after treatment with oily auxiliaries. Detailed Implementation

[0091] The present invention will now be described in detail and specifically through specific embodiments to enable a better understanding of the invention. However, the following embodiments do not limit the scope of the invention.

[0092] 4-[3-(trifluoromethyl)-3H-bis(acrylidine-3-yl)benzoic acid was purchased from Tianjin Kaimu Chemical Technology Co., Ltd. N,N-dihydroxyethylaniline, monomethyl malonate, dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 4-acetamidobenzenesulfonyl azide (p-ABSA) were purchased from Shanghai Titan Technology Co., Ltd. Unless otherwise specified, all purchased chemicals and solvents were used directly.

[0093] Each diazonium salt was prepared using a previously reported method, as shown in Table 1 below.

[0094] Table 1

[0095] product raw material References Diazonium salt of 2-amino-5-nitrothiazole 2-Amino-5-nitrothiazole Dyes and Pigments 2024, 222, 111840 diazonium salt of p-nitroaniline p-Nitroaniline Chemical Engineering Science 2026, 320(Part_A), 122430 Diazonium salt of 2-cyano-4-nitroaniline 2-Cyano-4-nitroaniline Dyes and Pigments 2022, 201, 110239 Aniline diazonium salt aniline Small 2025, 21(35), 2504051 2-Chloro-4-nitroaniline diazonium salt 2-Chloro-4-nitroaniline Dyes and Pigments 2025, 239, 112755 2,6-Dichloro-4-nitroaniline diazonium salt 2,6-Dichloro-4-nitroaniline Dyes and Pigments 2022, 201, 110239 Diazonium salt of 2-aminobenzothiazole 2-Aminobenzothiazole Journal of Molecular Structure 2024, 1306, 137931 Diazonium salt of 3-amino-5-nitrobenzisothiazole 3-Amino-5-nitrobenzisisothiazole Journal of Molecular Structure 2022, 1265, 133438

[0096] Example 1: Synthesis of Compound 1

[0097]

[0098] Dichloromethane (100 mL), N,N-dihydroxyethylaniline (20 mmol, 3.62 g), DCC (10 mmol, 2.06 g), and DMAP (1 mmol, 0.12 g) were added sequentially to a 250 mL three-necked flask. After stirring until homogeneous, monomethyl malonate (10 mmol, 1.18 g) was added dropwise over 5 min. After the addition was complete, the reaction was stirred for 1 h. After the reaction was complete, water (100 mL) was added for extraction. The resulting organic phase was dried over anhydrous sodium sulfate, filtered, and the low-boiling solvent (dichloromethane) was removed using a rotary evaporator. The residue was separated by silica gel column chromatography (eluent: V). 乙酸乙酯 / V 石油醚 = 1 / 10), to obtain compound 1, a white viscous substance, 1.13 g, yield 40%.

[0099] Compound 1: 1 H NMR (DMSO-d6, 400 M) δ 7.16 (dd, J 1 = 7.6 Hz, J 2 = 7.6 Hz, 2H), 6.73 (d, J = 8.0 Hz, 2H), 6.60 (dd, J 1 = 7.2 Hz, J 2 3.51 (s, 2H), 3.42 (t, J = 6.0 Hz, 2H). 13 CNMR (DMSO-d6, 100 M) δ 167.35, 167.09, 147.89, 129.60, 116.03, 111.87, 62.57,58.50, 53.35, 52.59, 49.40, 41.36. ESI-MS: m / z = 281.1[M] + The proton NMR spectrum of compound 1 is shown in [reference needed]. Figure 2 The carbon NMR spectrum of compound 1 is shown in [reference needed]. Figure 3 .

[0100] Example 2, Synthesis of Compound 2

[0101]

[0102] Dichloromethane (40 mL), compound 1 (4 mmol, 1.13 g), 4-[3-(trifluoromethyl)-3H-bisacryl-3-yl]benzoic acid (4 mmol, 1.15 g), DCC (4 mmol, 0.82 g), and DMAP (0.4 mmol, 0.05 g) were added sequentially to a 250 mL three-necked flask, followed by stirring for 1 h. After the reaction was complete, water (40 mL) was added for extraction. The resulting organic phase was dried over anhydrous sodium sulfate, filtered, and the low-boiling solvent (dichloromethane) was removed by rotary evaporation. The residue was then separated by silica gel column chromatography (eluent: V). 乙酸乙酯 / V 石油醚 = 1 / 15), yielding compound 2. Yellow viscous substance, 1.46 g, yield 74%.

[0103] Compound 2:1 H NMR(CDCl3, 400 M) δ 8.00 (d, J = 8.4 Hz, 2H), 7.25~7.22 (m,4H), 6.79 (d, J = 8.4 Hz, 2H), 6.74 (dd, J 1 = 7.2 Hz, J 2 = 7.2 Hz, 1H), 4.49(t, J = 6.0 Hz, 2H), 4.33 (t, J = 6.0 Hz, 2H), 3.76 (t, J = 6.0 Hz, 2H), 3.71(s, 3H), 3.69 (t, J = 6.0 Hz, 2H), 3.37 (s, 2H). 13 C NMR (CDCl3, 100 M) δ166.82, 166.48, 165.52, 147.15, 133.94, 131.02, 130.01, 129.59, 126.45,121.91(q, J = 273 Hz), 117.42, 112.39, 62.57, 62.55, 52.56, 49.75, 49.59,41.21, 28.47(q, J = 40 Hz). ESI-MS: m / z = 493.1 [M] + The proton NMR spectrum of compound 2 is shown in [reference needed]. Figure 4 The carbon NMR spectrum of compound 2 is shown in [reference needed]. Figure 5 .

[0104] Example 3, Synthesis of Compound 3

[0105]

[0106] Compound 2 (2.96 mmol, 1.46 g) and acetonitrile (30 mL) were added to a 100 mL three-necked flask and stirred until dissolved. DBU (3.10 mmol, 0.47 g) was then added, and the mixture was stirred for 10 min at room temperature. Subsequently, p-ABSA (3.10 mmol, 0.74 g) was added dropwise over 5 min, and the reaction was stirred for another 30 min after the addition was complete. After the reaction was complete, water (30 mL) was added, and the mixture was extracted three times with dichloromethane (30 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated using a rotary evaporator to remove low-boiling solvents (such as dichloromethane). The residue was separated by silica gel column chromatography (eluent: V). 乙酸乙酯 / V 石油醚= 1 / 15) to give compound 3, a yellow viscous substance, 1.37 g, yield 89%.

[0107] Compound 3: 1 H NMR(DMSO-d6, 400 M) δ 8.00 (d, J = 8.8 Hz, 2H), 7.26~7.22(m, 4H), 6.81 (d, J = 8.4 Hz, 2H), 6.74 (dd, J 1 = J 2 = 7.2 Hz, 1H), 4.49 (d, J = 6.0 Hz, 2H), 4.42 (d, J = 6.0 Hz, 2H), 3.82 (s, 3H), 3.77 (t, J = 6.0 Hz, 2H), 3.73 (t, J = 6.0 Hz, 2H). 13 C NMR (DMSO-d6, 100 M) δ 165.52, 161.24,161.13, 147.14, 133.98, 130.95, 129.99, 129.61, 126.43, 121.89 (q, J = 273Hz), 117.44, 112.35, 62.61, 62.51, 52.61, 49.62, 28.47 (q, J = 41 Hz). 19 F NMR(CDCl3, 400M) δ 65.39. ESI-MS: m / z = 519.1 [M] + The proton NMR spectrum of compound 3 is shown in [reference needed]. Figure 6 The carbon NMR spectrum of compound 3 is shown in [reference needed]. Figure 7 .

[0108] Example 4: Synthesis of Dye II

[0109]

[0110] A diazonium salt solution of 2-amino-5-nitrothiazole was added dropwise to a 250 mL three-necked flask containing 30 mL of methanol solution of compound 3 (2.6 mmol, 1.37 g) placed in an ice bath. The solution temperature was maintained between 0 and 5 °C during the addition, and the pH was maintained between 5 and 7 by adding sodium carbonate powder. Thin-layer chromatography was used to monitor the reaction until compound 3 was completely consumed. Water (200 mL) was then added, resulting in the precipitation of a solid. After standing, the solid was filtered through a Buchner funnel to obtain a crude product, which was further separated using silica gel column chromatography (eluent: V). 乙酸乙酯 / V石油醚 = 3 / 10), yielding dye II. Blue solid, 0.90 g, yield 51%.

[0111] Dye II: 1 H NMR(CDCl3, 400 M) δ 8.62 (s, 1H), 8.00 (d, J = 8.4 Hz, 2H), 7.96 (d, J = 9.2 Hz, 2H), 7.24 (d, J = 8.4 Hz, 2H), 6.94 (d, J = 9.2 Hz, 2H), 4.59 (t, J = 6.0 Hz, 2H), 4.51 (t, J = 6.0 Hz, 2H), 3.98 (t, J = 6.0 Hz, 2H), 3.91 (t, J = 6.0 Hz, 2H), 3.82 (s, 3H). 13 C NMR (CDCl3, 100 M) δ 180.67,165.39, 161.38, 160.70, 153.53, 147.70, 143.63, 143.55, 134.40, 130.42,129.98, 126.56, 121.83 (q, J = 273 Hz), 112.53, 62.15, 61.86, 52.64, 49.79,49.67. ESI-MS: m / z = 675.1 [M] + .

[0112] The proton NMR spectrum of dye II is shown below. Figure 8 The carbon NMR spectrum of dye II is shown in [reference needed]. Figure 9 .

[0113] Example 5: Synthesis of Dye III

[0114] A diazonium salt solution of p-nitroaniline was added dropwise to a 250 mL three-necked flask containing a 30 mL methanol solution of compound 3 (2.6 mmol, 1.37 g) placed in an ice bath. The solution temperature was maintained between 0 and 5 °C during the addition, and the pH was maintained between 5 and 7 by adding sodium carbonate powder. Thin-layer chromatography was used to monitor the reaction until compound 3 was completely consumed. Water (200 mL) was then added, resulting in the precipitation of a solid. After standing, the solid was filtered through a Buchner funnel to obtain a crude product, which was further separated using silica gel column chromatography (eluent: V). 乙酸乙酯 / V 石油醚= 1 / 10), yielding dye III. Red-orange solid, 1.36 g, yield 78%.

[0115] Dye III: 1 H NMR(CDCl3, 400 M) δ 8.33 (d, J = 9.2 Hz, 2H), 8.01 (d, J =8.4 Hz, 2H), 7.94 (d, J = 8.8 Hz, 2H), 7.78 (d, J = 8.8 Hz, 2H), 7.23 (d, J =8.4 Hz, 2H), 6.92 (d, J = 9.2 Hz, 2H), 4.57 (t, J = 6.0 Hz, 2H), 4.49 (t, J =6.0 Hz, 2H), 3.91 (t, J = 6.0 Hz, 2H), 3.86 (t, J = 6.0 Hz, 2H), 3.82 (s,3H). 13 C NMR (CDCl3, 100 M) δ 165.48, 161.27, 160.97, 150.89, 147.70, 144.51,144.00, 129.99, 129.05, 126.50, 126.19, 124.75, 122.88, 119.54, 111.92,62.30, 62.10, 52.65, 49.63, 49.54. ESI-MS: m / z = 668.2 [M] + .

[0116] The proton NMR spectrum of dye III is shown below. Figure 10 The carbon NMR spectrum of dye III is shown in [reference needed]. Figure 11 .

[0117] Example 6: Synthesis of Dye IV

[0118]

[0119] A diazonium salt solution of 2-cyano-4-nitroaniline was added dropwise to a 250 mL three-necked flask containing 30 mL of methanol solution of compound 3 (2.6 mmol, 1.37 g) placed in an ice bath. The solution temperature was maintained between 0 and 5 °C during the addition, and the pH was maintained between 5 and 7 by adding sodium carbonate powder. Thin-layer chromatography was used to monitor the reaction until compound 3 was completely consumed. Water (200 mL) was then added, resulting in the precipitation of a solid. After standing, the solid was filtered through a Buchner funnel to obtain a crude product, which was further separated using silica gel column chromatography (eluent: V).乙酸乙酯 / V 石油醚 = 1 / 10), yielding dye IV. Reddish-black solid, 1.06 g, yield 59%.

[0120] Dye IV: 1 H NMR(CDCl3, 400 M) δ 8.63 (d, J = 2.4 Hz, 1H), 8.45 (dd, J 1 =9.2 Hz, J 2 = 2.4 Hz, 1H), 7.99 (d, J = 9.2 Hz, 1H), 7.89 (d, J = 8.8 Hz, 2H), 7.78 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.4 Hz, 2H), 6.94 (d, J = 9.2 Hz, 2H), 4.59 (t, J = 6.0 Hz, 2H), 4.50 (t, J = 6.0 Hz, 2H), 3.95 (t, J = 6.0 Hz, 2H), 3.89 (t, J = 6.0 Hz, 2H), 3.82 (s, 3H). 13 C NMR (CDCl3, 100 M) δ 168.75,165.44, 160.88, 157.31, 152.38, 146.75, 143.89, 134.29, 132.73, 130.51,130.00, 129.09, 128.32, 126.52, 119.50, 118.05, 112.51, 112.16, 62.21, 61.94,52.68, 49.70, 49.60. ESI-MS: m / z = 693.2 [M] + .

[0121] The proton NMR spectrum of dye IV is shown below. Figure 12 The carbon NMR spectrum of dye IV is shown in [reference needed]. Figure 13 .

[0122] The UV-Vis absorption spectra of dyes II to IV in DMF are as follows: Figure 14 As shown, dye II has a maximum absorption wavelength of 575 nm and a molar extinction coefficient of 30400 L / (mol·cm); dye III has a maximum absorption wavelength of 476 nm and a molar extinction coefficient of 14860 L / (mol·cm); and dye IV has a maximum absorption wavelength of 521 nm and a molar extinction coefficient of 19650 L / (mol·cm).

[0123] The thermogravimetric curve (left) and differential scanning calorimetry curve (right) of dye II are shown in the figure. Figure 15 Thermogravimetric analysis (TGA) curves show that dye II experiences its first weight loss between 130℃ and 170℃, caused by the release of nitrogen gas from the bisacrylidine structure. A second weight loss occurs between 170℃ and 200℃, caused by the release of nitrogen gas from the diazo structure. Differential scanning calorimetry (DSC) curves show that dye II exhibits its first exothermic peak around 154℃, corresponding to the heat generated by the release of nitrogen gas from the bisacrylidine structure. A second exothermic peak appears around 190℃, corresponding to the heat generated by the release of nitrogen gas from the diazo structure. These results confirm that the transformation of the bisacrylidine and diazo structures at different temperature levels was indeed detected in the TGA and DSC experiments.

[0124] The thermogravimetric curve (left) and differential scanning calorimetry curve (right) of dye III are shown in the figure. Figure 16 The thermogravimetric curve (left) and differential scanning calorimetry curve (right) of dye IV are shown in the figure. Figure 17 .

[0125] Consistent with the results of dye II tests, the above tests all observed the transformation of the bisacrylidine and diazo structures at different temperature levels.

[0126] Examples 7-11, Synthesis of Dyes V-IX:

[0127] Compared to Example 4, the "diazonium salt of 2-amino-5-nitrothiazole" was changed to the diazonium salt described in Table 1, and the other steps were the same as in Example 4, thereby obtaining dyes V to IX respectively.

[0128] Table 1

[0129]

[0130] Dye V: Bright yellow solid, yield 66%. 1 H NMR(CDCl3, 400 M) δ 7.83~7.78 (m, 4H),7.73 (d, J = 7.6 Hz, 2H), 7.53 (d, J = 7.6 Hz, 2H), 7.47 (dd, J 1 = 7.6 Hz, J 2= 7.2 Hz, 2H), 7.34~7.30 (m, 1H), 6.99 (d, J = 7.2 Hz, 2H), 4.57 (t, J = 6.0Hz, 2H), 4.49 (t, J = 6.0 Hz, 2H), 3.91 (t, J = 6.0 Hz, 2H), 3.86 (t, J = 6.0Hz, 2H), 3.82 (s, 3H). ESI-MS: m / z = 623.2 [M] + .

[0131] Dye VI: Red solid, yield 57%. 1 H NMR(CDCl3, 400 M) δ 8.51 (d, J = 2.4 Hz,1H), 8.32 (dd, J 1 = 7.6 Hz, J 2 = 2.4 Hz, 1H), 8.01~7.96 (m, 3H), 7.83 (d, J =7.6 Hz, 2H), 7.56 (d, J = 7.6 Hz, 2H), 6.84 (d, J = 7.6 Hz, 2H), 4.56 (t, J =6.0 Hz, 2H), 4.48 (t, J = 6.0 Hz, 2H), 3.90 (t, J = 6.0 Hz, 2H), 3.85 (t, J =6.0 Hz, 2H), 3.81 (s, 3H). ESI-MS: m / z = 702.1 [M] + .

[0132] Dye VII: Orange solid, yield 62%. 1 H NMR(CDCl3, 400 M) δ 8.41 (s, 2H), 8.01 (d,J = 7.2 Hz, 2H), 7.93 (d, J = 7.6 Hz, 2H), 7.56 (d, J = 7.2 Hz, 2H), 7.07 (d,J = 7.6 Hz, 2H), 4.58 (t, J = 6.0 Hz, 2H), 4.50 (t, J = 6.0 Hz, 2H), 3.92 (t,J = 6.0 Hz, 2H), 3.87 (t, J = 6.0 Hz, 2H), 3.82 (s, 3H). ESI-MS: m / z = 736.1[M] + .

[0133] Dye VIII: Orange-red solid, yield 55%. 1 H NMR(CDCl3, 400 M) δ 8.13~8.11 (m, 1H),8.03~8.00 (m, 1H), 7.96 (d, J = 7.6 Hz, 2H), 7.58 (d, J = 7.6 Hz, 2H), 7.49(d, J = 7.6 Hz, 2H), 7.46~7.43 (m, 2H), 6.80 (d, J = 7.6 Hz, 2H), 4.59 (t, J= 6.0 Hz, 2H), 4.50 (t, J = 6.0 Hz, 2H), 3.95 (t, J = 6.0 Hz, 2H), 3.89 (t, J= 6.0 Hz, 2H), 3.82 (s, 3H). ESI-MS: m / z = 680.1 [M] + .

[0134] Dye IX: Blue solid, yield 72%. 1 H NMR(CDCl3, 400 M) δ 8.64 (d, J = 1.2 Hz,1H), 8.39 (dd, J 1 = 1.2 Hz, J 2 = 7.2 Hz, 1H), 7.98 (d, J = 7.6 Hz, 1H), 7.73(d, J = 7.6 Hz, 2H), 7.60 (d, J = 7.6 Hz, 2H), 7.55 (d, J = 7.2 Hz, 2H), 6.93(d, J = 7.2 Hz, 2H), 4.57 (t, J = 6.0 Hz, 2H), 4.49 (t, J = 6.0 Hz, 2H), 3.97(t, J = 6.0 Hz, 2H), 3.92 (t, J = 6.0 Hz, 2H), 3.83 (s, 3H). ESI-MS: m / z =725.1 [M] + .

[0135] Application methods of carbene dyes for dyeing polyester fabrics

[0136] (1) Carbene dye (50 mg), dispersant NNO (100 mg), deionized water (20 g) and zirconium beads (Φ0.3~0.4 mm, 50 g) were thoroughly mixed and then sand milled for 4 h. The zirconium beads were filtered out, and the residual dye in the zirconium beads was washed with a small amount of deionized water. The filtrates were combined and diluted to 50 mL with additional deionized water to obtain a dye dispersion.

[0137] (2) Prepare a dye bath using the dye dispersion obtained in step (1) and dye the polyester fabric (2 g). The dye dosage is 1% owf, the liquor ratio is 1:50, and the pH is 4~5. Dye at room temperature, raise the temperature to 130℃ at a rate of 2℃ / min, hold for 60 min, and then lower the temperature to 40℃ at a rate of 5℃ / min. Remove, wash with water, and air dry to obtain the dyed fabric.

[0138] (3) The dyed fabric obtained in step (2) is subjected to reduction cleaning. The reduction cleaning method adopts the conventional method in the field (i.e., the cleaning solution formula is sodium hydroxide (2 g / L) and sodium hydrosulfite (2 g / L), the bath ratio is 1:50, the cleaning temperature is 80 ℃, and the cleaning time is 10 min) to obtain the final dyed fabric.

[0139] Test methods

[0140] (1) Color fastness test method

[0141] The heat migration fastness of dyed polyester fabrics was tested according to the method provided in GB / T 44161—2024 "Determination of heat migration of disperse dyes". Specifically, the dyed polyester fabric was sandwiched between a white polyester lining and a white cotton lining of the same size, and hot-pressed for 30 s at a set temperature in a heating device consisting of two metal heating plates with a precisely controlled electric heating system. The combined sample was then removed, and the staining level of the lining fabric was evaluated according to GB / T 251 as the test result of heat migration.

[0142] The color fastness to washing of dyed polyester fabrics was tested according to the method provided in GB / T 3921-2008 "Textiles - Tests for color fastness to washing - Color fastness to washing", at a test temperature of 60℃.

[0143] The color fastness to rubbing of dyed polyester fabrics was tested according to the method provided in GB / T 3920-2008 "Textiles - Tests for color fastness - Color fastness to rubbing".

[0144] (2) Methods for treating oily additives

[0145] The surface of the dyed polyester fabric was immersed in silicone oil, and excess oil was removed using a padding machine. This process was repeated, known as a two-dip, two-paste process, which increased the fabric weight by approximately 5%. The heat migration fastness of the dyed polyester fabric was then tested.

[0146] (3) Fixation rate test method

[0147] Immerse 1 g of dyed polyester fabric in 10 mL of N,N-dimethylformamide at 120°C for 10 min. Remove the fabric and immerse it in another 10 mL of N,N-dimethylformamide at 120°C. Repeat the above operation until the N,N-dimethylformamide no longer has any color. Remove the fabric, rinse it three times with clean water, and air dry it. Test the K / S value of the treated fabric. The ratio of the K / S value of the treated fabric to the K / S value of the untreated fabric is taken as the fixation rate value.

[0148] Figure 18 The results show the heat migration fastness of fabrics dyed with Dye II (upper row) measured at 150–200°C. It can be seen that the polyester fabrics dyed with Dye II showed no staining on the cotton lining (middle row) and polyester lining (lower row) at 150–180°C, with only slight staining on the polyester lining at 190 and 200°C.

[0149] Figure 19 The study demonstrates the staining of cotton and polyester linings on fabric samples treated with oily auxiliaries after dye II dyeing at 150–200°C, based on the heat migration color fastness. Similarly, polyester fabrics dyed with dye II showed no staining on either cotton or polyester linings at 150–180°C, with only slight staining on the polyester lining at 190 and 200°C.

[0150] Similarly, the test results of the heat migration color fastness of fabrics dyed with dye III are as follows: Figure 20 As shown: Under test conditions of 150~200℃, no staining was observed on either cotton or polyester linings. The test results of the heat migration color fastness of the dyed fabrics after treatment with oily auxiliaries are as follows. Figure 21 As shown: No staining was observed on either cotton or polyester lining under test conditions of 150~200℃.

[0151] The test results of the heat migration color fastness of dyed fabrics with dye IV are as follows: Figure 22 As shown: only a trace amount of staining was observed on the polyester lining at 200℃. The test results for the heat migration color fastness of dye IV-dyed fabric samples after treatment with oily auxiliaries are as follows: Figure 23 As shown: only a small amount of staining was observed on the polyester lining at 200°C.

[0152] Table 2. Color fastness grades for heat migration of dyed polyester fabrics

[0153]

[0154] Note: All processing conditions were 180℃ for 30 seconds.

[0155] Table 2 shows that, under the test conditions of 180℃ and 30s, the dyed fabrics obtained in Examples 4 to 11 all exhibit excellent heat migration fastness grades. In particular, they demonstrate excellent heat migration fastness in the presence of oily auxiliaries.

[0156] Table 3. Color fastness grades for washing and rubbing of dyed polyester fabrics

[0157]

[0158] The results in the table above show that the dyed fabrics obtained in Examples 4 to 11 all have excellent color fastness to washing and color fastness to rubbing.

[0159] Comparative Example 1: Synthesis of the contrast dye F1

[0160] The structure of contrast dye F1 is as follows:

[0161]

[0162] F1

[0163] The synthetic route for contrast dye F1 is as follows:

[0164]

[0165] Using 4-trifluoroacetylbenzoic acid (4 mmol, 0.87 g) instead of 4-[3-(trifluoromethyl)-3H-bisacrididin-3-yl]benzoic acid (4 mmol, 1.15 g), otherwise as described in Example 2, compound 4 (a yellow viscous liquid, yield 93.8%) was obtained. ESI-MS: m / z = 481.1 [M] + .

[0166] Using compound 4 (2.6 mmol, 1.25 g) instead of compound 3 (2.6 mmol, 1.37 g), otherwise as described in Example 4, we obtained the comparative dye F1 (blue solid, 79% yield). ESI-MS: m / z = 637.1 [M] + .

[0167] Comparative Example 2: Synthesis of the contrast dye F2

[0168] The structure of contrast dye F2 is as follows:

[0169]

[0170] F2

[0171] The synthetic route for contrast dye F2 is as follows:

[0172]

[0173] Using compound 4 (2.96 mmol, 1.43 g) instead of compound 2 (2.96 mmol, 1.46 g), and otherwise as described in Example 3, compound 5 (a yellow viscous liquid, yield 61.2%) was obtained. ESI-MS: m / z = 507.1 [M] + .

[0174] Using compound 5 (2.6 mmol, 1.32 g) instead of compound 3 (2.6 mmol, 1.37 g), otherwise as described in Example 4, we obtained the comparative dye F2 (blue solid, yield 53.3%). ESI-MS: m / z = 663.1 [M] + .

[0175] Comparative Example 3: Synthesis of contrast dye F3

[0176] The structure of contrast dye F3 is as follows:

[0177]

[0178] F3

[0179] The synthetic route for contrast dye F3 is as follows:

[0180]

[0181] Using compound 2 (2.6 mmol, 1.28 g) instead of compound 3 (2.6 mmol, 1.37 g), otherwise as described in Example 4, we obtained the comparative dye F3 (blue solid, yield 79.3%). ESI-MS: m / z = 649.1 [M] + .

[0182] Comparative Example 4: Existing bisacrylidine dyes

[0183] The contrast dye F4 is the dye reported in the literature (Dyes and Pigments 2026, 246, 113416).

[0184]

[0185] F4

[0186] Comparative Example 5: Existing Diazo Dyes

[0187] The contrast dye F5 is the dye reported in the patent (CN119592098).

[0188]

[0189] F5

[0190] The performance results obtained from the above comparative examples are shown in Tables 4 and 5 below.

[0191] Table 4

[0192]

[0193] Note: All heat treatment conditions are 180℃ for 30 seconds.

[0194] As shown in Table 4, the fixation rate of polyester fabric dyed with dye II is only 33.4%, indicating that the proportion of dye molecules that are covalently bonded to the fiber is low. This further indicates that the excellent heat migration resistance of the polyester fabric dyed by the present invention is not solely due to the chemical reaction between the dye and the fiber, but more so due to the self-crosslinking reaction of the dye molecules within the fiber.

[0195] Because dye F1 in Comparative Example 1 has no reactive groups, the dyed polyester fabric has no color-fixing effect and the dye molecules themselves have no cross-linking ability. Therefore, the dye molecules in the dyed fabric are more likely to migrate, resulting in lower color fastness.

[0196] The dye F2 in Comparative Example 2 has only one reactive group and is a 2-diazomalonic acid diester structure. This structure has a high thermal response temperature, which prevents the dye molecules in the dyed polyester fabric from being converted. It cannot react chemically with the fiber efficiently, nor can it undergo cross-linking reaction.

[0197] Dye F3 in Comparative Example 3 has only one bisacrylidine group, which is a conventional bisacrylidine dye. Similar to the literature reports, this dye has a good reaction effect with polyester fibers, and the fixation rate can reach about 57%.

[0198] The staining characteristics of polyester fabrics dyed with dyes F1 to F5 at 150-200℃ are as follows:

[0199] The test results of the heat migration color fastness of the fabric dyed with contrast dye F1 are as follows: Figure 24 As shown: the dyed fabric showed no significant staining on polyester and cotton linings at 150~200℃. The heat migration color fastness test results of the contrast dye F1-dyed fabric samples after oily auxiliary agent treatment are as follows: Figure 25 As shown: the dyed fabric caused severe staining of both polyester and cotton linings at 150~200℃.

[0200] The test results of the heat migration color fastness of fabrics dyed with contrast dye F2 are as follows: Figure 26As shown: the dyed fabric only caused slight staining of the polyester lining at 190 and 200°C. The heat migration color fastness test results of the contrast dye F2-dyed fabric sample after treatment with oily auxiliaries are as follows: Figure 27 As shown: the dyed fabric caused severe staining of both polyester and cotton linings at 150~200℃.

[0201] The test results of the heat migration color fastness of fabrics dyed with contrast dye F3 are as follows: Figure 28 As shown: the dyed fabric showed no significant staining on polyester and cotton linings at 150~200℃. The heat migration color fastness test results of the contrast dye F3-dyed fabric sample after oily auxiliary agent treatment are as follows: Figure 29 As shown: the dyed fabric produces obvious staining on both polyester and cotton linings at 150~180℃, and severe staining at 190~200℃.

[0202] The test results of the heat migration fastness of the existing bisacrylidine dye-dyed fabric in Comparative Example 4 are as follows: the dyed fabric showed no obvious staining on the polyester and cotton linings at 150~200℃. The test results of the heat migration fastness of the existing bisacrylidine dye-dyed fabric sample in Comparative Example 4 after treatment with oily auxiliaries are as follows: the dyed fabric showed obvious staining on the polyester and cotton linings at 180~200℃.

[0203] The test results of the heat migration fastness of the existing diazo dye-dyed fabric in Comparative Example 5 were as follows: the dyed fabric caused obvious staining on the polyester lining at 180~200℃. The test results of the heat migration fastness of the existing diazo dye-dyed fabric sample after treatment with oily auxiliaries in Comparative Example 5 were as follows: the dyed fabric caused severe staining on the polyester and cotton linings at 150~200℃.

[0204] When dyes F1 to F3 are not treated with oily auxiliaries, the staining of dyed polyester onto the interlining is not obvious. However, when dyed polyester fabrics are treated with oily auxiliaries, both polyester and cotton interlinings show obvious staining. Explanation: Compared to the dyes of this invention, the problem with dye F1 is that it has no reactive groups at all, and the dye does not undergo any change in the fiber. The dye in dyed polyester migrates very easily, especially in the presence of oily auxiliaries, where dye molecules easily transfer to the white interlining. The problem with dye F2 is that it only has a 2-diazomalonic acid diester structure, which can only transform at temperatures above 150°C. It cannot undergo chemical transformation in the 130°C dyeing environment of this invention; therefore, dye molecules in polyester fabrics dyed with dye F2 also migrate very easily. The problem with dye F3 is that it only has a diaziridine structure. Although it has a high fixation rate, the dye molecules that do not react with the fiber cannot form intramolecular or intermolecular crosslinks as in this invention, and still migrate significantly in the presence of oily auxiliaries. Comparative Example 4, dye F4, has two identical reactive groups (bisacrylidine structure). The dyed polyester fabric exhibits a lower fixation rate, but its heat migration fastness in the presence of oil is higher than that of Comparative Examples 1-3, possibly due to its larger molecular weight. However, it is still inferior to the dyed fabric produced by the dye of this invention. Comparative Example 5, dye F5, is similar to dye F2, possessing only one 2-diazomalonic acid diester structure, but its molecular weight is smaller. Under the application conditions of this invention, the dye cannot undergo any chemical reaction with the fiber or itself, and the dye migrates very easily. As described in patent (CN119592098), dye F5 requires a high-temperature fixation step after high-temperature and high-pressure dyeing to achieve a chemical reaction between the dye and polyester, thus exhibiting high migration resistance.

[0205] Table 5. Color fastness grades for washing and rubbing of dyed polyester fabrics

[0206]

[0207] Table 5 shows that the dyed fabrics obtained from Comparative Examples 1 to 3 all exhibit excellent color fastness to washing and rubbing. Comparative Example 4, due to its excessively large dye molecules, resulted in poor dyeing and a higher number of surface dye molecules, leading to slightly lower color fastness to rubbing. Comparative Example 5 also showed slightly lower color fastness to washing.

[0208] The above results indicate that only dye molecules with two specific reactive groups, as provided in this invention, can enable dyed polyester to exhibit excellent heat migration resistance in high-temperature and high-pressure dyeing systems.

[0209] Comparative application example 1:

[0210] The polyester fabric was dyed using dye IV according to the dyeing application method of the present invention, but without the third step of reduction cleaning, to obtain dyed polyester fabric, and its heat migration fastness was tested.

[0211] The test results for the heat migration fastness of dye IV-dyed polyester fabric (without reduction cleaning) in the presence of oil were as follows: Under test conditions of 150~200℃, relatively obvious staining occurred on both polyester and cotton linings. This is because the dyed fabric did not undergo a reduction cleaning step, resulting in a small amount of loose dye on the fiber surface, which transferred to the lining fabric during the test.

[0212] Finally, it should be noted that the above examples are merely some specific embodiments of the present invention. Obviously, the present invention is not limited to the above embodiments and many variations are possible. All variations that can be directly derived or conceived by those skilled in the art from the disclosure of the present invention should be considered within the scope of protection of the present invention.

Claims

1. A carbene dye containing two isoreactive groups, characterized in that, Its general structural formula is as follows: ； Among them, R 1 and R 2 They are selected from hydrogen atoms, methyl groups, methoxy groups, and acetamido groups, respectively. Ar is selected from any of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 。 2. The carbene dye containing two isoreactive groups according to claim 1, characterized in that... The structural formula is any of the following: 、 、 、 、 、 、 、 。 3. The method for synthesizing carbene dyes containing two different reactive groups as described in claim 1 or 2, characterized in that... Includes the following steps: (1) Compound M is condensed with monomethyl malonate to obtain compound N; (2) Compound N was condensed with 4-[3-(trifluoromethyl)-3H-bisacryl-3-yl]benzoic acid to obtain compound P; (3) Compound P is reacted with a diazo group transfer reaction to obtain compound Q; (4) Using compound Q as the coupling component, a coupling reaction is carried out with the corresponding diazonium salt to obtain a carbene dye containing two different reactive groups; The structure of compound M is as follows: ， The structure of compound N is as follows: ， The structure of compound P is as follows: ， The structure of compound Q is as follows: ， Among them, R 1 and R 2 They are selected from hydrogen atoms, methyl groups, methoxy groups, and acetamido groups, respectively. The diazonium salt is any one of the following: 、 、 、 、 、 、 、 、 、 、 、 、 。 4. The method for synthesizing carbene dyes containing two different reactive groups according to claim 3, characterized in that: Compound M is N,N-dihydroxyethylaniline.

5. The application of the carbene dye containing two isoreactive groups as described in claim 1 or 2 in the dyeing of polyester fabrics.

6. The application according to claim 5, characterized in that... Includes the following steps: S1. After thoroughly mixing the carbene dye, dispersant, and water, the mixture is milled to obtain a dye dispersion. S2. The polyester fabric is dyed using the dispersion obtained in step S1 to obtain a dyed fabric; the dyeing temperature is 130±5℃. S3. Perform a reduction cleaning on the dyed fabric obtained in step S2.

Images