Reactive black dye composition, ink-jet ink and preparation method of ink-jet ink

Abstract

The invention provides an active black dye composition, ink-jet ink and a preparation method of the ink-jet ink. The active black dye composition comprises a component A shown in a formula (1): # imgabs 0, R1 and R2 independently represent H and C1-C6 alkyl groups, or a component B shown in a formula (2): # imgabs 1 #, R3 represents H, C1-C6 alkyl groups, hydroxyl groups or-SO3H, and a component B shown in a formula (3): # imgabs 2 #. The total mass of the active black dye composition is 100%, the content of the component A is 18%-90%, and the content of the component B is 1%-43%. The ink-jet ink containing the active black dye composition is excellent in fluency and stability, high in compatibility, excellent in deep dyeing property and good in various fastness when being used for jet printing on fabrics, can meet the requirements of fast consumer markets, and plays roles in energy conservation, emission reduction and environmental protection at the same time.

Description

Technical Field

[0001] The present invention relates to an active black dye composition, an inkjet ink and a preparation method thereof, belonging to the field of dyes. Background Art

[0002] Digital inkjet printing is being used more and more widely due to its flexibility, economic applicability and environmental protection characteristics, and its market share is increasing year by year. Traditional black dyeing has high energy consumption, large amount of wastewater and simple patterns, while digital inkjet printing can well meet the needs of the fast consumer market: less dye consumption, small batches, personalization, less wastewater in post-treatment, energy saving and environmental protection.

[0003] As the main color, black has high requirements for the shade, color depth and dyeing fastness of dyes. Currently, the existing black inks have problems such as a large amount of dye wastewater, low dye uptake rate, low dyeing fastness, low compatibility and poor storage stability.

[0004] Therefore, it has become an urgent technical problem to study an active black dye composition and an inkjet ink that not only have deep coloration, good blackness and good fastness, but also have good adaptability of dye components and good storage stability and can be widely used in the inkjet field. Summary of the Invention

[0005] Problems to be Solved by the Invention

[0006] In view of the technical problems existing in the prior art, the present invention first provides an active black dye composition and an inkjet ink containing the active black dye composition. The inkjet ink using the active black dye composition of the present invention has excellent fluidity and stability, high compatibility, excellent dyeing depth when printed on fabrics, and good fastnesses, can meet the needs of the fast consumer market, and at the same time plays a role in energy conservation, emission reduction and environmental protection.

[0007] The present invention also provides a preparation method of an inkjet ink. The preparation method is simple and easy to operate, the raw materials are easy to obtain, and it is suitable for large-scale production.

[0008] Solutions for Solving the Problems

[0009] The present invention provides an active black dye composition, which comprises:

[0010] Component A shown in formula (1):

[0011]

[0012] Wherein, R1 and R2 each independently represent H, an alkyl group having 1 to 6 carbon atoms or

[0013] Component B shown in formula (2):

[0014]

[0015] Among them, R3 represents H, an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or -SO3H;

[0016] Based on the total mass of the reactive black dye composition being 100%, the content of component A is 18% - 90%, and the content of component B is 1% - 43%.

[0017] The reactive black dye composition according to the present invention, wherein the reactive black dye composition further comprises component D represented by formula (5) or formula (6):

[0018]

[0019] Among them, R6 represents H or -SO3Na;

[0020]

[0021] Among them, R7 represents H or -SO3Na, and R8 and R9 each independently represent H, an alkyl group having 1 to 6 carbon atoms or a phenyl group.

[0022] The reactive black dye composition according to the present invention, wherein based on the total mass of the reactive black dye composition being 100%, the content of component D is 0.1% - 35%.

[0023] The reactive black dye composition according to the present invention, wherein the reactive black dye composition further comprises component E represented by formula (7):

[0024]

[0025] Among them, R 10 , R 11 each independently represent H, an alkyl group having 1 to 6 carbon atoms or

[0026] The reactive black dye composition according to the present invention, wherein based on the total mass of the reactive black dye composition being 100%, the content of component E is 0.1% - 15%.

[0027] The present invention also provides an inkjet ink, which comprises a reactive black dye composition, an auxiliary agent, an organic solvent and an inorganic solvent; wherein, the reactive black dye composition is the reactive black dye composition according to any one of claims 1 - 5;

[0028] Preferably, based on the total mass of the inkjet ink being 100%, the content of the active black dye composition is 15% - 20%, the content of the auxiliary agent is 0.5% - 3%, the content of the organic solvent is 30 - 50%, and the content of the inorganic solvent is 27% - 54.5%.

[0029] For the inkjet ink according to the present invention, wherein the auxiliary agent includes a surfactant and / or a bactericide; preferably, the content of the surfactant is 0.5% - 2%, and the content of the bactericide is 0.01% - 1%.

[0030] For the inkjet ink according to the present invention, wherein the organic solvent includes alcohol compounds, preferably including one or more combinations of ethylene glycol, glycerol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, pentylene glycol, polyvinyl alcohol, etc.

[0031] For the inkjet ink according to the present invention, wherein the surfactant includes an alkynediol surfactant; and / or, the bactericide includes an isothiazolinone bactericide.

[0032] The present invention also provides a preparation method of the inkjet ink according to the present invention, which includes the step of mixing each component of the inkjet ink.

[0033] Effects of the Invention

[0034] The inkjet ink using the active black dye composition of the present invention has excellent fluidity and stability, high compatibility, excellent dyeing depth when inkjet printing on fabrics, good fastness in all aspects, can meet the needs of the fast - consumption market, and at the same time plays a role in energy conservation, emission reduction and environmental protection.

[0035] The preparation method of the inkjet ink of the present invention is simple and feasible, the raw materials are easy to obtain, and it is suitable for mass production. Detailed Embodiments

[0036] The following will detail various exemplary embodiments, features and aspects of the present invention. The special word "exemplary" here means "serving as an example, an embodiment or an illustration". Any embodiment described as "exemplary" here does not have to be construed as superior to or better than other embodiments.

[0037] In addition, in order to better illustrate the present invention, numerous specific details are given in the following detailed embodiments. Those skilled in the art should understand that the present invention can still be implemented without some specific details. In other instances, methods, means, equipment and steps well - known to those skilled in the art are not described in detail so as to highlight the gist of the present invention.

[0038] Unless otherwise specified, the units used in this specification are all international standard units, and the numerical values and numerical ranges appearing in the present invention should be understood to include the inevitable systematic errors in industrial production.

[0039] In this specification, the meaning expressed by using "may" includes the meanings of both performing a certain process and not performing a certain process.

[0040] In this specification, the "some specific / preferred embodiments", "other specific / preferred embodiments", "embodiments", etc. mentioned refer to the specific elements (e.g., features, structures, properties, and / or characteristics) related to the embodiment, which are included in at least one of the embodiments described herein, and may or may not exist in other embodiments. Additionally, it should be understood that the elements can be combined in various embodiments in any suitable manner.

[0041] In this specification, the numerical range expressed by using "numerical value A to numerical value B" refers to the range including the endpoint numerical values A and B.

[0042] <First aspect>

[0043] The first aspect of the present invention provides an active black dye composition, which includes:

[0044] Component A shown in formula (1):

[0045]

[0046] wherein, R1 and R2 each independently represent H, an alkyl group of C1 - C6 or

[0047] Component B shown in formula (2):

[0048]

[0049] wherein, R3 represents H, an alkyl group of C1 - C6, a hydroxyl group or -SO3H;

[0050] wherein, based on the total mass of the active black dye composition being 100%, the content of component A is 18% - 90%, for example: 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, etc.; the content of component B is 1% - 43%, for example: 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, etc.

[0051] In the present invention, component A shown in formula (1) may be a compound shown in the following formula (1 - 1) or (1 - 2):

[0052]

[0053] In the present invention, component B represented by formula (2) may be a compound represented by the following formula (2-1) or (2-2):

[0054]

[0055] In some specific embodiments, the reactive black dye composition further comprises component D represented by formula (5) or formula (6):

[0056]

[0057] wherein, R6 represents H or -SO3Na;

[0058]

[0059] wherein, R7 represents H or -SO3Na, and R8 and R9 each independently represent H, an alkyl group having 1 to 6 carbon atoms or a phenyl group;

[0060] Preferably, based on the total mass of the reactive black dye composition being 100%, the content of component D is 0.1% - 35%, for example: 1%, 5%, 10%, 15%, 20%, 25%, 30%, etc.

[0061] Specifically, in the present invention, component C represented by formula (5) may be a compound represented by the following formula (5-1) or (5-2):

[0062]

[0063] In the present invention, component C represented by formula (6) may be a compound represented by the following formula (6-1) or (6-2):

[0064]

[0065]

[0066] In some specific embodiments, the reactive black dye composition further comprises component E represented by formula (7):

[0067]

[0068] wherein, R 10 , R 11 each independently represent H, an alkyl group having 1 to 6 carbon atoms or

[0069] Preferably, based on the total mass of the reactive black dye composition being 100%, the content of component E is 0.1% - 15%, for example: 1%, 3%, 5%, 7%, 9%, 11%, 13%, etc.

[0070] Specifically, in the present invention, component E represented by formula (7) can be a compound represented by the following formula (7-1) or (7-2):

[0071]

[0072] In some specific embodiments, the reactive black dye composition of the present invention further comprises component C represented by formula (3) or formula (4):

[0073]

[0074] wherein, R4 and R5 each independently represent H or

[0075] Preferably, based on the total mass of the reactive black dye composition being 100%, the content of component C is 0% - 25%, for example: 1%, 5%, 10%, 15%, 20%, etc.

[0076] Specifically, in the present invention, component C represented by formula (3) can be a compound represented by the following formula (3-1) or (3-2):

[0077]

[0078] In the present invention, component C represented by formula (4) can be a compound represented by the following formula (4-1) or (4-2):

[0079]

[0080]

[0081] The inkjet ink prepared from the reactive black dye composition of the present invention has excellent fluidity and stability, high compatibility, excellent dyeing depth when printed on fabrics, good fastness in all aspects, can meet the needs of the fast consumer market, and at the same time plays a role in energy conservation, emission reduction and environmental protection.

[0082] <Second aspect>

[0083] The second aspect of the present invention provides an inkjet ink, which comprises a reactive black dye composition, an auxiliary agent, an organic solvent and an inorganic solvent; wherein, the reactive black dye composition is the reactive black dye composition according to the present invention;

[0084] Preferably, based on the total mass of the ink-jet ink being 100%, the content of the active black dye composition is 15%-20%, for example: 16%, 17%, 17%, 19%, etc.; the content of the auxiliary agent is 0.5%-3%, for example: 1%, 1.5%, 2%, 2.5%, etc.; the content of the organic solvent is 30-50%, for example: 32%, 35%, 38%, 40%, 42%, 45%, 48%, etc.; the content of the inorganic solvent is 27%-54.5%, for example: 30%, 32%, 35%, 38%, 40%, 42%, 45%, 48%, 50%, 52%, etc.

[0085] In some specific embodiments, the auxiliary agent includes a surfactant and / or a bactericide; preferably, the content of the surfactant is 0.5%-2%, for example: 0.8%, 1%, 1.2%, 1.5%, 1.8%, etc.; the content of the bactericide is 0.01%-1%, for example: 0.05%, 0.1%, 0.3%, 0.5%, 0.8%, etc.

[0086] Specifically, the organic solvent includes alcohol compounds, preferably including one or a combination of two or more of ethylene glycol, glycerol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, pentylene glycol, polyvinyl alcohol, etc. The inorganic solvent includes water.

[0087] The surfactant in the present invention includes alkynediol surfactants, for example: Evonik Surfynol440, Evonik Surfynol 465, etc.

[0088] The bactericide used in this embodiment is an isothiazolinone bactericide. For example: methylisothiazolinone (MIT), N-octyl-4-isothiazolin-3-one (OIT), etc. By using the bactericide, while ensuring that the fabric is not invaded by microorganisms and is environmentally friendly, the compatibility with other components of the ink can be taken into account, and at the same time, no foam is generated during use, which is convenient to use and has good stability.

[0089] The second aspect of the present invention also provides a preparation method of the ink-jet ink according to the present invention, which includes the step of mixing the components of the ink-jet ink.

[0090] Specifically, after mixing the components of the ink-jet ink evenly, the solid impurities therein are removed to obtain the ink-jet ink. In order to mix evenly, stirring or ultrasonic means can be used. Further, the solid impurities are removed by centrifugal separation or filtration to obtain the ink-jet ink.

[0091] Examples

[0092] The embodiments of the present invention will be described in detail below in conjunction with examples. However, those skilled in the art will understand that the following examples are only used to illustrate the present invention and should not be regarded as limiting the scope of the present invention. For those not specified in the examples, the operations are carried out under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used without indicating the manufacturer are all conventional products that can be obtained through commercial purchase.

[0093] Examples 1 - 5

[0094] According to the composition in Table 1 below, after mixing each component and stirring well, filter to obtain the inkjet ink.

[0095] Table 1 Unit: %

[0096]

[0097] Examples 6 - 10

[0098] According to the composition in Table 2 below, after mixing each component and stirring well, filter to obtain the inkjet ink.

[0099] Table 2 Unit: %

[0100]

[0101] Examples 11 - 15

[0102] According to the composition in Table 3 below, after mixing each component and stirring well, filter to obtain the inkjet ink.

[0103] Table 3 Unit: %

[0104]

[0105] Examples 16 - 25

[0106] According to the composition in Table 4 below, after mixing each component and stirring well, filter to obtain the inkjet ink.

[0107] Table 4 Unit: %

[0108]

[0109] Examples 26 - 35

[0110] According to the composition in Table 5 below, after mixing each component and stirring well, filter to obtain the inkjet ink.

[0111] Table 5 Unit: %

[0112]

[0113] Performance Test

[0114] Preparation of Color Fastness Test Cloth Samples

[0115] 1. Prepare 100 g of ink samples each according to the above-mentioned embodiments. After filtering the prepared inks using instruments such as a suction flask (filter membrane 0.45 μm) in the laboratory, draw color block patterns on a small flatbed machine and then print color blocks on woven cotton cloth through a nozzle.

[0116] 2. After pre-drying the color block samples (drying under the conditions of 55 °C for 5 min), perform steam evaporation and color development in a steam box (conditions: 102 °C for 15 min).

[0117] 3. After the color development and fixation in step 2 are completed, perform washing and soaping (soaping conditions: 95 °C for 10 min, bath ratio: cloth sample: soaping water = 1:50, by weight).

[0118] 4. After soaping, iron dry the color block cloth samples and keep the surface of the cloth samples flat for testing color fastness.

[0119] 1. Color Fastness Test

[0120] This patent compares the washing fastness, perspiration fastness, sunlight fastness, and rubbing fastness of each embodiment. The detection methods all adopt the standards generally recognized in the industry, as shown in Table 6 - 10 below, where:

[0121] The washing fastness test standard is AATCC 61 - 2A; the perspiration fastness detection standard is GB / T 3922; the sunlight fastness test standard is AATCC 20h; the rubbing fastness detection standard is GB / T 3920.

[0122] Table 6 Examples 1 - 5 Unit: Grade

[0123]

[0124] Table 7 Examples 6 - 10 Unit: Grade

[0125]

[0126] Table 8 Examples 11 - 15 Unit: Grade

[0127]

[0128] Table 9 Examples 16 - 25 Unit: Grade

[0129]

[0130] Table 10 Examples 26 - 35 Unit: Grade

[0131]

[0132] As can be seen from Table 6-10, the color fastnesses of the inkjet ink of the present invention are all excellent.

[0133] 2. Lab Value and Color Density Tests

[0134] Lab value detection method: Detection is completed using a color difference meter. The color difference meter uses the CIE-defined Lab color space for color measurement and comparison. The specific steps are as follows:

[0135] 2.1. Calibrate the color difference meter: Adjust the instrument to ensure that its output accurately reflects the standardized color space. Usually, a standard white board or reference standard is used to adjust the color response of the instrument.

[0136] 2.2. Prepare the samples: Ensure that the samples meet the required standards or specifications in terms of color. This may involve preparing standard color samples as a comparison benchmark, or preparing products or materials to be evaluated.

[0137] 2.3. Measure the Lab value:

[0138] Align the color difference meter with the sample to be measured for detection. Maintain stable environmental conditions, such as light and temperature, to avoid the influence of external factors on the measurement results. The results are shown in Table 11-15 below.

[0139] For each sample, perform three measurements and calculate the average value to improve the accuracy and repeatability of the measurement results.

[0140] Ensure that the position and orientation of the sample remain consistent during the measurement process, especially for large-sized or non-uniform samples.

[0141] 2.4. Analyze and compare: After the measurement is completed, the color difference meter will generate the Lab value of the sample, including brightness (L), red-green tone (a), and yellow-blue component (b). Compare the measured Lab value with the reference value or standard to evaluate whether the color of the sample meets the requirements, or to judge the magnitude of the color difference.

[0142] Color density test: Detection is completed using a densitometer, which can measure the density value of the color on the surface of printed matter or other objects. This measurement is crucial for ensuring color consistency and quality.

[0143] During the test, first, a stable light source is used to irradiate the object to be measured, and then the amount of reflected light is measured. During this process, the color filter only allows light of a specific wavelength to pass through in order to measure the density of a specific color. For example, by using red, green, and blue color filters, Dr (red density), Dg (green density), and Db (blue density) can be measured respectively. These three parameters can accurately represent the color attributes of a certain color sample. The results are shown in Table 11-15 below.

[0144] Table 11 Lab Value and Color Density Data of Examples 1-5

[0145] Example L* a* b* DE* Parts by Weight / % Color Density 1 28.88 -1.37 -12.46 Standard Sample Standard Sample 1.15 2 27.65 -0.83 -10.55 2.50 102 1.14 3 29.88 -2.43 -14.67 3.25 103.5 1.15 4 28.98 -1.14 -12.16 0.65 98.2 1.12 5 25.84 1.02 -3.56 4.24 97.5 1.03

[0146] Table 12 Lab values and color density data of Examples 6 - 10

[0147] Example L* a* b* DE* Parts by Weight / % Color Density 6 28.22 0.66 -13.06 Standard Sample Standard Sample 1.16 7 27.90 2.10 -11.78 2.2 100.2 1.18 8 27.81 2.51 -11.42 2.4 100.3 1.19 9 28.12 1.52 -12.67 1.5 100.5 1.17 10 27.82 2.0 -11.67 2.1 100.1 1.18

[0148] Table 13 Lab values and color density data of Examples 11 - 15

[0149] Example L* a* b* DE* Parts by Weight / % Color Density 11 27.28 1.75 -11.58 Standard Sample Standard Sample 1.15 12 27.34 2.45 -10.78 2.1 100.1 1.16 13 27.56 2.25 -11.10 1.7 100.2 1.17 14 28.34 3.50 -9.70 3.5 99.6 1.12 15 28.56 4.5 -5.45 4.5 98.4 1.05

[0150] Table 14 Lab values and color density data of Examples 16 - 25

[0151] Example L* a* b* DE* Parts by Weight / % Color Density 16 27.34 1.61 -11.35 Standard Sample Standard Sample 1.13 17 28.90 1.98 -8.75 1.5 98.9 1.05 18 27.56 1.78 -9.45 1.2 99.1 1.08 19 27.44 1.68 -9.87 1.1 99.8 1.10 20 27.21 1.51 -10.23 0.95 100.1 1.12 21 27.34 1.78 -11.20 0.85 99.2 1.10 22 28.45 1.83 -9.78 1.4 100.3 1.11 23 27.56 1.92 -8.89 1.5 97.5 1.05 24 27.47 1.98 -8.56 1.6 97.3 1.03 25 27.65 1.97 -8.89 1.5 97.4 1.04

[0152] Table 15 Lab values and color density data of Examples 26 - 35

[0153] Example L* a* b* DE* Parts by Weight / % Color Density 26 26.76 0.57 -3.20 Standard Sample Standard Sample 1.13 27 27.23 0.89 -2.78 0.7 98.7 1.12 28 27.34 1.03 -2.98 0.8 98.3 1.11 29 28.61 1.21 -1.78 0.9 97.9 1.04 30 29.12 2.06 -1.09 1.5 97.5 1.01 31 28.34 2.10 0.51 2.5 97.0 0.95 32 29.83 1.23 1.50 1.65 98.7 0.96 33 26.78 0.65 -0.50 1.10 98.6 1.02 34 27.11 0.75 -1.23 1.12 98.3 1.05 35 26.78 1.04 -1.56 0.67 99.8 1.12

[0154] As can be seen from Tables 11 - 15, the ink - jet ink of the present invention has excellent dyeing performance when printed on fabrics.

[0155] It should be noted that although the technical solutions of the present invention are introduced by specific examples, those skilled in the art can understand that the present invention should not be limited thereto.

[0156] The embodiments of the present invention have been described above. The above description is exemplary, not exhaustive, and is not limited to the disclosed embodiments. Many modifications and variations are obvious to those of ordinary skill in the art in the technical field without departing from the scope and spirit of the described embodiments. The selection of the terms used herein is intended to best explain the principles of the embodiments, practical applications, or improvements to the technology in the market, or to enable other ordinary skill in the art in the technical field to understand the disclosed embodiments.

Claims

1. An active black dye composition, characterized in that, Comprising: Component A shown in formula (1): wherein, R1 and R2 each independently represent H, an alkyl group having 1 to 6 carbon atoms, or Component B shown in formula (2): Wherein, R3 represents H, an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or -SO3H; Based on the total mass of the reactive black dye composition being 100%, the content of Component A is 18% - 90%, and the content of Component B is 1% - 43%.

2. The reactive black dye composition according to claim 1, characterized in that, The reactive black dye composition further comprises Component D shown in formula (5) or formula (6): Wherein, R6 represents H or -SO3Na; Wherein, R7 represents H or -SO3Na, and R8 and R9 each independently represent H, an alkyl group having 1 to 6 carbon atoms or a phenyl group.

3. The reactive black dye composition according to claim 2, wherein Based on the total mass of the reactive black dye composition being 100%, the content of Component D is 0.1% - 35%.

4. The reactive black dye composition according to any one of claims 1 to 3, characterized in that, The reactive black dye composition further comprises Component E shown in formula (7): wherein, R 10 , R 11 each independently represents H, an alkyl group having 1 to 6 carbon atoms or 5. The reactive black dye composition according to claim 4, characterized in that, Based on the total mass of the reactive black dye composition being 100%, the content of Component E is 0.1% - 15%.

6. An inkjet ink, characterized in that, Comprising a reactive black dye composition, an auxiliary agent, an organic solvent and an inorganic solvent; wherein, the reactive black dye composition is the reactive black dye composition according to any one of claims 1 - 5; Preferably, based on the total mass of the inkjet ink being 100%, the content of the reactive black dye composition is 15% - 20%, the content of the auxiliary agent is 0.5% - 3%, the content of the organic solvent is 30 - 50%, and the content of the inorganic solvent is 27% - 54.5%.

7. The inkjet ink according to claim 6, wherein The auxiliary agent includes a surfactant and / or a bactericide; preferably, the content of the surfactant is 0.5% - 2%, and the content of the bactericide is 0.01% - 1%.

8. The inkjet ink according to claim 6 or 7, characterized in that, The organic solvent includes alcohol compounds, preferably including one or a combination of two or more of ethylene glycol, glycerol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, pentylene glycol, polyvinyl alcohol, etc.

9. The inkjet ink according to claim 7, wherein The surfactant includes alkynediol surfactants; and / or, the bactericide includes isothiazolinone bactericides.

10. A method for preparing an inkjet ink according to any one of claims 6-9, characterized in that, Comprising the step of mixing each component of the inkjet ink.

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