Dispersant for disperse dye ink and its application

Abstract

This invention relates to the field of digital inkjet printing inks, specifically a dispersant for disperse dye inks and its use in high-temperature direct-injection disperse dye inks. The dispersant structure is shown in Formula I, with the substituents detailed in the specification. The dispersant designed in this invention is consistent with the main structure of the disperse dye and disperses between dye molecules, hindering their aggregation, acting as a dispersant. Furthermore, it lacks hydrophilic groups and is insoluble in water. During the fixation stage, it dyes polyester fabrics together with the dye and is not present in wastewater from post-processing, thus resolving the issue of colored wastewater. #imgabs0#

Description

Technical Field

[0001] The present invention relates to the field of digital inkjet printing ink, and in particular to a disperse dye ink dispersant and application thereof in high-temperature direct-jet disperse dye ink. Background Art

[0002] Digital inkjet printing is rapidly developing in textile printing applications. Inkjet printing inks for textiles not only have specific requirements for dye purity, insoluble solid particle size, ink viscosity, surface tension, stability, pH, and foaming properties, but also require excellent dyeing properties after the ink is sprayed onto the fabric to form a pattern, including minimal color difference and high color fastness.

[0003] In digital textile printing, high-temperature dispersible direct-jet inks offer advantages over medium- and low-temperature sublimation inks used in thermal transfer printing, such as high permeability, a superior feel to printed fabrics, and superior color fastness. However, existing technologies for high-temperature dispersible direct-jet inks still have drawbacks, such as insufficient storage stability. To maintain the particle size and storage stability achieved after dye grinding, various dispersants are often added in large quantities, significantly increasing ink costs and negatively impacting the environment.

[0004] Prior art reports on high-temperature dispersed inks exist, such as CN111501376A, CN112796119A, and CN107724114A, which disclose methods for preparing high-temperature dispersed inks. However, these methods provide only qualitative descriptions of their stability, or are omitted. The inventors previously addressed the dispersion stability issue in CN113914116B by developing a novel self-produced dispersant. While the dispersant described in this report provides good dispersion, it also exhibits inherent color and is water-soluble. Dispersants deposited on textiles during the inkjet process can cause wastewater treatment issues, hindering widespread application. Summary of the Invention

[0005] The purpose of the present invention is to solve the problems of existing dispersants having their own color and dispersion stability, and the problem of colored wastewater caused by dyeing fabrics with dispersants and dyes. A disperse dye ink dispersant and its application in high-temperature direct-jet disperse dye ink are provided.

[0006] To achieve the above purpose, the present invention adopts the following technical solutions:

[0007] A dispersant for disperse dye ink, the dispersant structure is shown in Formula I:

[0008]

[0009] Wherein, X is selected from C3-C20 alkyl, C3-C6 cycloalkyl, C3-C6 heterocyclic group which are unsubstituted or substituted with at least one of the following substituents; the following substituents are C1-C6 alkyl, phenyl; wherein the heteroatom in the heterocyclic group is S, N or O.

[0010] Preferably, in the dispersant formula I, X is selected from a C3-C12 alkyl group or a C3-C6 heterocyclic group which is unsubstituted or substituted with at least one of the following substituents; the following substituents are C1-C6 alkyl groups or phenyl groups; wherein the heteroatom in the heterocyclic group is S.

[0011] Further preferably, in the dispersant formula I, X is preferably selected from -CH(CH3)2, -C(CH3)3, 4-dodecyl, 4-phenylethyl, tetrahydro-2-thienyl, tetrahydro-3-thienyl, 5-methyl-tetrahydro-2-thienyl, 4-tetrahydro-thiopyranyl, and the specific structural formula is as follows:

[0012]

[0013]

[0014] An application of the disperse dye ink dispersant, and an application of the dispersant represented by formula I in high-temperature direct-jet yellow disperse ink.

[0015] The invention discloses a high-temperature direct-jet yellow disperse ink. The high-temperature direct-jet yellow disperse ink comprises, by weight percentage, 3-15% of a high-temperature yellow disperse dye, 1-15% of a dispersant, 30-60% of an organic solvent, 0.5-2% of a surfactant, 0.05-0.2% of a bactericide, 0.1-0.5% of a defoaming agent, and the balance being deionized water.

[0016] The high temperature disperse dye includes one or more high temperature disperse yellow dyes, and the high temperature disperse yellow dye includes one or more of CI Disperse Yellow 73, CI Disperse Yellow 114, CI Disperse Yellow 134, and CI Disperse Yellow 163.

[0017] The organic solvent is one or more of glycerol, isopropyl alcohol, diethylene glycol, thiodiglycol, and ethylene glycol monomethyl ether.

[0018] The surfactant is one or a mixture of Surfynol465, fatty acid polyoxyethylene ether AEO, and TN-6;

[0019] The defoaming agent is one or both of Surfynol-104E and APE-0050;

[0020] The fungicide is one or a mixture of 5-chloro-2-methyl-4-isothiazoline-3-one, 1,6-dihydroxy-2,5-dioxane, and 1,2-benzisothiazolin-3-one fungicides;

[0021] A method for preparing a high-temperature direct-injection blue disperse ink comprises the following steps: mixing a high-temperature disperse dye and a dispersant, by mass percentage, at room temperature, and grinding the mixture in a grinder using zirconium beads with a diameter of 0.20-0.35 mm for 8-40 hours to obtain a dispersion; mixing the dispersion, an organic solvent, a surfactant, a bactericide, a defoamer, and deionized water, stirring the mixture at a speed of 2200-2800 r / min for 1-5 hours, and filtering the mixture to obtain the high-temperature disperse direct-injection ink.

[0022] An application of the high-temperature direct-jet dispersed ink is to apply the ink to direct printing on a digital textile printing machine, controlling the working temperature to be 15-35°C and the working humidity to be 20-80%; drying the printed product and steaming for color fixation, wherein the steaming temperature is 160-200°C and the steaming time is 8-12 minutes.

[0023] The present invention has the following advantages:

[0024] The dispersant designed in the present invention has the same main structure as the disperse dye, is dispersed between the dye molecules, and plays a role in hindering the aggregation of the dye molecules, that is, the dispersant function; at the same time, it has no hydrophilic group and is insoluble in water. It dyes polyester fabrics together with the dye in the fixation stage and will not exist in the wastewater of the post-processing fabric, thus solving the problem of colored wastewater. DETAILED DESCRIPTION

[0025] The following specific examples are provided to further illustrate the present invention, but the present invention is in no way limited to these examples. Various modifications may be made within the scope defined by the claims. The disperse dyes in the examples are commercially available. The homemade dispersants were synthesized using conventional organic synthesis methods. The organic solvents, surfactants, fungicides, defoamers, and deionized water are all commercially available and were purchased unless otherwise specified.

[0026] Example 1

[0027] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 10% CI Disperse Yellow 114, 1% homemade dispersant Y-1, 20% organic solvent isopropyl alcohol, 5% organic solvent ethylene glycol monomethyl ether, 0.5% surfactant Surfynol 465, 0.3% surfactant fatty acid polyethylene ether AEO, 0.1% bactericide 1,6-dihydroxy-2,5-dioxane, 0.2% defoaming agent Surfynol 104E, and 62.9% deionized water.

[0028] Example 2

[0029] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 12% of CI Disperse Yellow 114, 1.2% of a self-made dispersant Y-2, 13% of a solvent diethylene glycol, 8.8% of thiodiglycol, 5% of an organic solvent ethylene glycol monomethyl ether, 0.5% of a surfactant TN-6, 0.15% of a fungicide 1,2-benzisothiazolin-3-one, 0.1% of a defoamer APE-0050, and 59.25% of deionized water.

[0030] Example 3

[0031] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 8% CI Disperse Yellow 114, 0.8% self-made dispersant Y-3, 18% organic solvent glycerol, 7% organic solvent ethylene glycol monomethyl ether, 0.6% surfactant Surfynol-104E, 0.1% fungicide 5-chloro-2-methyl-4-isothiazoline-3-one, 0.1% defoamer APE-0050, and 65.4% deionized water.

[0032] Example 4

[0033] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 12% CI Disperse Yellow 114, 1.2% dispersant Y-4, 13% organic solvent diethylene glycol, 8.8% thiodiglycol, 5% organic solvent ethylene glycol monomethyl ether, 0.5% surfactant Surfynol 465, 0.3% surfactant TN-6, 0.1% bactericide 1.2-benzisothiazolin-3-one, 0.2% defoamer APE-0050, and 58.9% deionized water.

[0034] Example 5

[0035] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 8% CI Disperse Yellow 114, 51% dispersant Y-, 25% organic solvent glycerol, 5% organic solvent ethylene glycol monomethyl ether, 0.5% surfactant Surfynol 465, 0.3% surfactant TN-6, 0.2% surfactant fatty acid polyoxyethylene ether AEO, 0.1% TN-6 fungicide 1,2-benzisothiazolin-3-one, 0.2% defoamer APE-0050, and 59.7% deionized water.

[0036] Example 6

[0037] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 10% CI Disperse Yellow 114, 1.2% dispersant Y-6, 13% organic solvent diethylene glycol, 8.8% isopropyl alcohol, 5% organic solvent ethylene glycol monomethyl ether, 0.5% surfactant Surfynol 465, 0.3% surfactant TN-6, 0.1% bactericide 1.2-benzisothiazolin-3-one, 0.2% defoamer APE-0050, and 60.9% deionized water.

[0038] Example 7

[0039] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 10% CI Disperse Yellow 114, 0.9% dispersant Y-7, 12% organic solvent diethylene glycol, 9.8% isopropyl alcohol, 5.5% organic solvent ethylene glycol monomethyl ether, 0.5% surfactant Surfynol 465, 0.3% surfactant TN-6, 0.1% bactericide 1.2-benzisothiazolin-3-one, 0.2% defoamer APE-0050, and 60.7% deionized water.

[0040] Example 8

[0041] A yellow high-temperature direct-jet disperse ink comprises, by mass percentage, 12% of CI Disperse Yellow 114, 1.2% of dispersant Y-8, 25% of organic solvent glycerol, 5% of organic solvent ethylene glycol monomethyl ether, 0.5% of surfactant Surfynol 465, 0.3% of surfactant TN-6, 0.2% of surfactant fatty acid polyoxyethylene ether AEO, 0.1% of TN-6 fungicide 1,2-benzisothiazolin-3-one, 0.2% of defoamer APE-0050, and 55.5% of deionized water.

[0042] Examples 9 to 18

[0043] In Examples 1 to 8, the structures of dispersants Y-1 to Y-8 are as follows:

[0044]

[0045]

[0046] Synthesis of Dispersant Y-1: 3-nitrophenyl-4-(1-methylethyl)benzenesulfonate is reduced with iron powder to obtain 3-aminophenyl-4-(1-methylethyl)benzenesulfonate, which is diazotized with dilute hydrochloric acid and sodium nitrite and reacted with the coupling component of CI Disperse Yellow 114 to obtain Dispersant Y-1.

[0047] 1H NMR(500MHz,Chloroform-d)δ7.81–7.75(m,1H),7.51–7.39(m,1H),7.42–7.37( m,1H),7.18–7.12(m,1H),3.35(s,1H),2.95–2.84(m,1H),1.27(d,J=6.6Hz,3H).

[0048] Synthesis method of dispersant Y-2: According to the synthesis method of dispersant Y-1, the raw material is replaced with 3-nitrophenyl-4-(1,1-dimethylethyl)benzenesulfonate.

[0049] 1H NMR (500MHz, Chloroform-d) δ7.79–7.73(m,1H),7.51–7.45(m,1H),7.47–7.39(m,1H),7.18–7.12(m,1H),3.35(s,1H),1.34(s,4H).

[0050] Synthesis method of dispersant Y-3: According to the synthesis method of dispersant Y-1, the raw material is replaced with 3-nitrophenyl-4-dodecylbenzenesulfonate.

[0051] 1H NMR(500MHz,Chloroform-d)δ7.81–7.75(m,1H),7.51–7.39(m,1H),7.33(dt,J=9.3,1.0Hz,1H),7.18–7.12(m,1H),3.35(s ,1H),2.62(tt,J=7.9,1.0Hz,1H),1.66–1.56(m,1H),1.37–1.28(m,3H),1.30–1.25(m,4H),1.27(s,2H),0.94–0.85(m,2H).

[0052] Synthesis of Dispersant Y-4: 4-(2-phenylethyl)benzenesulfonyl chloride and 3-nitrophenol react in dichloromethane at 0°C to prepare 3-nitrophenyl-4-(2-phenylethyl)benzenesulfonate. This is then reduced with iron powder to yield 3-aminophenyl-4-(2-phenylethyl)benzenesulfonate, which is then diazotized with dilute hydrochloric acid and sodium nitrite and reacted with the coupling component of CI Disperse Yellow 114 to yield Dispersant Y-4.

[0053] 1H NMR (500MHz, Chloroform-d) δ7.81–7.75(m,1H),7.51–7.39(m,1H),7.35(dt,J=9.2,1.0Hz,1H),7.29–7.12(m,4H),3.35(s,1H),2.91(s,2H).

[0054] Synthesis method of dispersant Y-5: According to the synthesis method of dispersant Y-4, the raw material is replaced with 3-nitrobenzene-4-(tetrahydro-3-thienyl)benzenesulfonyl chloride.

[0055] 1H NMR(500MHz,Chloroform-d)δ7.86–7.80(m,2H),7.48(dt,J=7.5,1.5Hz,1H),7.46–7.38(m,2H),7.42–7.36(m,1H),7.18–7.12(m,2H),4.05 (td,J=3.7,0.8Hz,1H),3.35(s,2H),2.88(dd,J=4.5,3.4Hz,2H),2.30–2.21(m,1H),2.16(dtd,J=12.3,5.7,3.4Hz,1H),2.03–1.96(m,2H).

[0056] Synthesis method of dispersant Y-6: According to the synthesis method of dispersant Y-4, the raw material is replaced with 3-nitrobenzene-4-(tetrahydro-2-thienyl)benzenesulfonyl chloride.

[0057] 1H NMR(500MHz,Chloroform-d)δ7.82–7.75(m,2H),7.48(dt,J=7.5,1.5Hz,1H),7.46–7.39(m,1H),7.35(dt,J=9.4,1.2 Hz,2H),7.18–7.12(m,2H),3.35(s,2H),3.33–3.26(m,1H),3.08–2.96(m,4H),2.32–2.23(m,1H),2.22–2.13(m,1H).

[0058] Synthesis method of dispersant Y-7: According to the synthesis method of dispersant Y-4, the raw material is replaced with 3-nitrobenzene-4-(tetrahydro-2H-thiopyran-4-yl)benzenesulfonyl chloride.

[0059] 1H NMR(500MHz,Chloroform-d)δ7.86–7.80(m,2H),7.51–7.35(m,3H),7.18–7.12(m,1 H),4.13–4.08(m,1H),3.35(s,2H),3.10(qt,J=4.4,3.2Hz,1H),2.17(dddd,J=12.3, 6.6,4.8,3.3Hz,1H),2.02(dddd,J=12.3,6.4,4.8,3.4Hz,1H),1.86(dddd,J=12.3,6 .6,4.8,3.2Hz,1H),1.68(dddd,J=12.4,6.8,4.8,3.3Hz,1H),1.26(d,J=4.4Hz,3H).

[0060] Synthesis method of dispersant Y-8: According to the synthesis method of dispersant Y-4, the raw material is replaced with 3-nitrobenzene-4-(tetrahydro-2H-thiopyran-4-yl)benzenesulfonyl chloride.

[0061] 1H NMR(500MHz,Chloroform-d)δ7.82–7.75(m,1H),7.51–7.39(m,1H),7.38–7.32 (m,1H),7.18–7.12(m,1H),3.35(s,1H),2.81–2.69(m,2H),2.16–2.00(m,2H).

[0062] Preparation method of dye ink: CI Disperse Yellow 114, dispersant, organic solvent, surfactant, defoamer and deionized water are mixed uniformly according to the formulas in Examples 1 to 8, and ground in a grinder until the dye particles are less than 0.5 μm to prepare a disperse dye dispersion. Then, a fungicide is added and mixed uniformly to obtain different yellow inks.

[0063] Comparative Example

[0064] Yellow ink was prepared according to the preparation method in Example 3 of patent CN113914116B.

[0065] The following performance indicators were measured at room temperature for the disperse dye inks of Examples 1-8 of the present invention and the comparative example.

[0066] 1. Measurement indicators and methods

[0067] a) Particle size: Dilute the disperse dye paste with deionized water to a certain multiple, and measure the particle size of the dye in the dispersed system using a nanoparticle size distribution analyzer at 25°C.

[0068] b) Viscosity: The viscosity of the ink was measured at 25°C using a rotational viscometer with a No. 0 rotor (torque of 50%).

[0069] c) pH: Measure the pH of the ink at 25°C using an EL-20 pH meter. Test each sample three times and take the average value. d) Redispersibility: Use a visible light spectrophotometer to measure the ABS value at the maximum absorption peak of the ink, recorded as ABS1. Place 20g of ink in a 100ml glass beaker, open in a 40°C oven for 48 hours, weigh the dried solution, then add high-purity water to the original weight. Stir with a magnetic stirrer for 30 minutes. Filter out any unredispersed dried ink using a 10µm syringe filter. Then, use a visible light spectrophotometer to measure the ABS value at the maximum absorption peak of the redispersed ink solution, recorded as ABS2. Ink redispersibility = ABS2 / ABS1*100%.

[0070] 2. Thermal storage stability test method

[0071] The disperse dye inks described in Examples 1-8 and the comparative example were sealed and left to stand in an electric blast drying oven at 60° C. for 14 days. The performance indicators a to d of the disperse dye inks were then measured again using the above method. The measurement results are shown in Table 2 below:

[0072] 3. Dyeing performance test method

[0073] A standard sample of CI Disperse Yellow 114 commercial dye was dyed according to the national standard GB / T 2374-2017. Examples 1-8 and the comparative example were printed spectrophotometrically using an EPSON L310 printer on sized polyester fabric, with the concentration adjusted to match the standard sample. The dyeing was then performed using steam. The wash water color of the standard sample of CI Disperse Yellow 114 commercial dye, the dyed fabric samples of Examples 1-8, and the comparative example was compared, and the wash water absorbance was measured using a PE Lambda 750 spectrophotometer.

[0074] The above performance test results are shown in Table 1, Table 2 and Table 3.

[0075] Table 1 Physical and chemical properties test results

[0076]

[0077] Table 2. Thermal storage stability performance test results

[0078]

[0079] Table 3. Absorbance test results of dyed cloth sample washing water

[0080]

[0081] Comparing the data in Table 1, Table 2 and Table 3, we can see that:

[0082] (1) The disperse dye inks described in Examples 1-8 showed similar particle size, pH value, and redispersion rate to those of the comparative example, demonstrating good redispersion properties. The viscosity values of Examples 1-8 were slightly greater than those of the comparative example, but met the ink viscosity index requirements.

[0083] (2) After thermal storage, the particle size performance indexes of Examples 1-8 did not change much from the initial measured particle size indexes, indicating that the disperse dye inks described in Examples 1-8 of the present invention had good thermal storage stability and had good dispersion stability compared with the comparative example;

[0084] (3) As for the color of the washing water of the dyed cloth sample, the washing water of the comparative example ink dyed cloth sample is light yellow, while the washing water of Examples 1 to 8 and the standard sample dyed cloth is colorless, indicating that the dispersant of the present invention has good dispersibility and solves the problem of colored washing water in CN113914116B.

Claims

1. An application of a disperse dye ink dispersant, characterized in that, Application of dispersants in high temperature direct jet yellow disperse ink; The dispersant structure is shown in Formula I: Formula I Wherein, X is selected from C3~C20 alkyl, C3~C6 cycloalkyl, C3~C6 heterocyclic group which are unsubstituted or substituted with at least one of the following substituents; the following substituents are C1~C6 alkyl and phenyl; wherein the heteroatom in the heterocyclic group is S, N or O.

2. The use according to claim 1, characterized in that In the dispersant formula I, X is selected from a C3-C12 alkyl group or a C3-C6 heterocyclic group which is unsubstituted or substituted with at least one of the following substituents; the following substituents are C1-C6 alkyl groups or phenyl groups; wherein the heteroatom in the heterocyclic group is S.

3. A high-temperature direct-injection yellow disperse ink, characterized by: The high-temperature direct-jet yellow disperse ink comprises, by mass percentage, 3-15% of a high-temperature yellow disperse dye, 1-15% of the dispersant according to claim 1, 30-60% of an organic solvent, 0.5-2% of a surfactant, 0.05-0.2% of a bactericide, 0.1-0.5% of a defoaming agent, and the balance being deionized water.

4. The high-temperature direct-injection yellow disperse ink according to claim 3, characterized in that: The high temperature yellow disperse dye includes one or more high temperature disperse yellow dyes.

5. The high-temperature direct-injection yellow disperse ink according to claim 3, characterized in that: The organic solvent is one or more of glycerol, isopropyl alcohol, diethylene glycol, thiodiglycol, and ethylene glycol monomethyl ether.

6. The high-temperature direct-injection yellow disperse ink according to claim 3, characterized in that: The surfactant is one or both of Surfynol465 and fatty acid polyoxyethylene ether AEO; The defoaming agent is Surfynol-104E; The fungicide is one or a mixture of 5-chloro-2-methyl-4-isothiazoline-3-one, 1,6-dihydroxy-2,5-dioxane, and 1,2-benzisothiazolin-3-one fungicides.

7. A method for preparing the high-temperature direct-injection yellow disperse ink according to claim 3, characterized in that: Calculated by mass percentage, at room temperature, a high-temperature yellow disperse dye and a dispersant are mixed, and then ground in a grinder using zirconium beads with a diameter of 0.20-0.35 mm for 8-40 hours to obtain a dispersion. The dispersion, an organic solvent, a surfactant, a fungicide, a defoamer, and deionized water are mixed, stirred at a speed of 2200-2800 r / min for 1-5 hours, and filtered to obtain the filtrate, which is the high-temperature direct-injection yellow disperse ink.

8. An application of the high-temperature direct-jet yellow disperse ink according to claim 3, characterized in that: The high-temperature direct-jet yellow disperse ink is applied to a digital textile printing machine for direct printing, and the working temperature is controlled at 15-35° C. and the working humidity is controlled at 20-80%. The printed product is dried and steamed for color fixation, and the steaming temperature is 160-200° C. and the steaming time is 8-12 minutes.

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