High weatherable washable macromolecular dye

Abstract

The present application relates to the technical field of dyes, in particular to a high-weather-resistance washable macromolecular dye. The high-weather-resistance washable macromolecular dye is prepared by condensation reaction of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone and polyethylene glycol under alkaline conditions based on the hydrophilicity of polyether chain and the stability of anthraquinone skeleton. The prepared high-weather-resistance washable macromolecular dye has the characteristics of bright color, easy washing, good light resistance and strong oxidation resistance, and has a wide range of applications, especially for educational ink and daily chemical products.

Description

Technical Field

[0001] This invention relates to the field of dye technology, and in particular to a highly weather-resistant, washable macromolecular dye. Background Technology

[0002] Polyether dyes, with their excellent migration resistance, color fastness, and transparency, have expanded into colored resins, engineering plastics, and foam materials, covering emerging markets such as daily chemical products and stationery. Through molecular structure modification (such as the introduction of polyethylene glycol segments), these dyes can also function as surfactants, significantly improving their hydrophilicity and giving them unique advantages in educational inks and daily chemical products (such as colored soaps and washable nail polish).

[0003] The current technical pain point and breakthrough direction lies in the washability problem: traditional solutions rely on adding washable auxiliaries to acid dyes, but have drawbacks such as high cost and obvious residue (difficult to remove stains from hands / fabric).

[0004] Novel macromolecular dyes (such as the thallium rose red dye in patent US005250708A and the red diazo coupling dye in CN116322633A) achieve self-cleaning and washability through structural design, requiring no additional auxiliaries. However, their performance needs to be upgraded: in the educational field, lightfastness needs to be improved (e.g., UV fading resistance for outdoor stationery); in the daily chemical field, antioxidant properties need to be enhanced to adapt to new base materials (e.g., soaps containing peroxides, fragrance-containing beads, etc.). Due to structural limitations, thallium-based and diazo coupling dyes are still weaker than anthraquinone dyes in terms of lightfastness / oxidation resistance, and there is an urgent need to develop heterocyclic modified structures to overcome performance bottlenecks.

[0005] Therefore, this application develops a multifunctional integrated high weather-resistant macromolecular dye that combines washability, sun resistance, and antioxidant properties. Summary of the Invention

[0006] In view of the shortcomings of the prior art described above, the purpose of this invention is to provide a highly weather-resistant and washable macromolecular dye that solves the problems of dyes being difficult to wash, having poor lightfastness, and weak antioxidant capacity in the prior art, based on the hydrophilicity of the polyether chain and the stability of the anthraquinone skeleton.

[0007] To achieve the above and other related objectives, the present invention is obtained through the following technical solution.

[0008] The first aspect of this invention is to provide a highly weather-resistant, washable macromolecular dye, comprising a dye macromolecule, the structural formula of which is as follows: , where n is 4-23.

[0009] In some embodiments of the present invention, the dye macromolecule is prepared by the following steps: S1, 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone is condensed with polyethylene glycol under alkaline conditions to form a dye macromolecule; S2, the dye macromolecule obtained in S1 is pH adjusted to obtain the dye macromolecule.

[0010] In some embodiments of the present invention, the polyethylene glycol is selected from PEG200-1000.

[0011] In some embodiments of the present invention, the alkaline condition mentioned in S1 refers to: pH ≥ 10; the alkaline condition is obtained by adding an alkali, wherein the alkali is selected from at least one of potassium hydroxide, potassium carbonate, triethylamine, sodium carbonate, and sodium hydroxide, wherein the molar ratio of the alkali to 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone is (1.1-2.2):1.

[0012] In some embodiments of the present invention, the temperature of the condensation reaction is 100-150°C.

[0013] In some embodiments of the present invention, S2 is adjusted using a pH adjuster, and the adjusted pH value is 7-10; the pH adjuster is selected from hydrochloric acid and dilute sulfuric acid.

[0014] In some embodiments of the present invention, the polyethylene glycol is PEG600 and the alkali is potassium carbonate.

[0015] In some embodiments of the present invention, the temperature of the condensation reaction is 130-150°C.

[0016] In some embodiments of the present invention, the high weather-resistant washable macromolecular dye further includes any one or a combination of two or more of the following raw materials: preservatives, water, and surfactants.

[0017] In some embodiments of the present invention, the high weather-resistant washable macromolecular dye has a viscosity ≤700mPa.s, a surface tension of 20-60mN / m, and a color concentration of 2.4±0.15Abs / (g / L·cm) at an absorption coefficient wavelength of 550nm.

[0018] A second aspect of the present invention is to provide an application of the aforementioned high weather-resistant, washable macromolecular dye for use in educational inks and daily chemical products.

[0019] As described above, the high weather-resistant, washable macromolecular dye of the present invention has the following beneficial effects:

[0020] (1) The macromolecular dye obtained by the present invention through condensation reaction using specific materials has bright colors, is easy to wash with water, and does not easily leave residues on hands, clothes, floors, etc.

[0021] (2) The macromolecular dye of the present invention has the characteristics of good lightfastness and strong antioxidant ability, and has a wide range of applications, especially suitable for stationery inks and daily chemical products. Attached Figure Description

[0022] Figure 1 This is a schematic diagram of the condensation reaction of the present invention.

[0023] Figure 2 This is a test diagram for the washability of highly weather-resistant, washable macromolecular dyes. Detailed Implementation

[0024] To make the inventive objectives, technical solutions, and beneficial effects of this invention clearer, the invention will be further described in detail below with reference to embodiments. Those skilled in the art can easily understand other advantages and effects of this invention from the content disclosed in this specification.

[0025] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the specification of this invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0026] When using “including,” “having,” and “contains” as described herein, the intention is to cover non-exclusive inclusion, unless an explicit qualifying term such as “only,” “consisting of,” etc., is used, in which case another component may be added.

[0027] In this invention, the terms "preferredly," "more preferably," "better," and "even better" refer to embodiments of the invention that provide certain beneficial effects under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of the invention. That is, in this invention, "preferredly," "more preferably," "better," and "even better" are merely descriptions of more effective implementations or examples, but do not constitute a limitation on the scope of protection of the invention.

[0028] In this invention, terms such as "further," "even more," and "particularly" are used for descriptive purposes and indicate differences in content, but should not be construed as limiting the scope of protection of this invention.

[0029] In this invention, "at least one" means one or more, such as one, two, or more. "Multiple" or "several" means at least two, such as two, three, etc., and "multi-layered" means at least two layers, such as two layers, three layers, etc., unless otherwise explicitly specified. In the description of this invention, "several" means at least one, such as one, two, etc., unless otherwise explicitly specified.

[0030] When a numerical range is disclosed herein, the range is considered continuous and includes the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Furthermore, when the range refers to integers, it includes every integer between the minimum and maximum values ​​of the range. Additionally, when multiple ranges are provided to describe a feature or characteristic, the ranges may be combined. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges to which they are incorporated.

[0031] Unless otherwise stated, a singular term may include a plural term and should not be interpreted as having a quantity of one.

[0032] In this invention, "above" or "below" both include the number itself. For example, "below 1" includes 1.

[0033] The first aspect of this invention is to provide a highly weather-resistant washable macromolecular dye, the key point of which is that the highly weather-resistant washable macromolecular dye includes a novel dye macromolecule, which is obtained by condensation reaction of a 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone compound with polyethylene glycol under alkaline conditions and neutralization by a pH adjuster.

[0034] The dye macromolecules of this invention combine the hydrophilicity of polyether chains with the stability of anthraquinone skeletons, resulting in enhanced wash resistance, sun resistance, and antioxidant properties. Polyethylene glycol has good hydrophilicity, thus ensuring both excellent washability and UV absorption intensity, thereby improving the dye's cost-effectiveness.

[0035] In some embodiments of the present invention, the molecular weight of polyethylene glycol is between 200 and 1000.

[0036] In some specific embodiments of the present invention, polyethylene glycol may be PEG200, PEG400, PEG600, PEG800 and PEG1000, or polyethylene glycol with any molecular weight between 200 and 1000.

[0037] More preferably, the polyethylene glycol is PEG600.

[0038] Polyethylene glycol (PEG) has good hydrophilicity. PEG with a molecular weight of 200-1000 can ensure both excellent washability and UV absorption intensity of the dye, thus improving its cost-effectiveness. If the molecular weight is too low, it may reduce washability; if the molecular weight is too high, it may affect the color value.

[0039] In some specific embodiments of the present invention:

[0040] In some embodiments of the present invention, alkaline conditions are obtained by adding a base in the condensation reaction. The alkaline conditions are: pH ≥ 10, specifically, pH = 10, pH = 11, pH = 12 or any specific value between 10 and 14.

[0041] In some embodiments of the present invention, the base added in the condensation reaction may be potassium hydroxide, potassium carbonate, triethylamine, sodium carbonate, or sodium hydroxide.

[0042] More preferably, the base added in the condensation reaction is potassium carbonate.

[0043] Potassium carbonate is selected because it has the highest conversion rate in the condensation reaction, less inorganic salt residue, less change in color value, and less noticeable change in hue.

[0044] In some embodiments of the present invention, the temperature range of the condensation reaction is 100-150°C.

[0045] In some embodiments of the present invention, the temperature of the condensation reaction can be 100°C, 110°C, 120°C, 130°C, 140°C, 150°C, or any specific value among 100°C and 150°C.

[0046] In some embodiments of the present invention, the temperature range for the condensation reaction with better reaction effect is 130-150°C.

[0047] In some embodiments of the present invention, the optimal temperature for the condensation reaction is 140°C.

[0048] In condensation reactions, temperatures that are too high or too low will cause the reaction to fail.

[0049] In some embodiments of the present invention, the pH adjuster is selected from hydrochloric acid and sulfuric acid.

[0050] In some specific embodiments of the present invention, the pH value after adjustment by the pH adjuster is 7-10. Specifically, it can be pH=7, pH=8, pH=9, pH=10, or any specific value between 7 and 10.

[0051] More preferably, the pH adjuster is sulfuric acid.

[0052] In theory, the pH adjuster in this invention can be any acid capable of neutralizing alkali. However, it is important to note that the finished dye product should not contain too much salt, otherwise it will affect its performance.

[0053] In some embodiments of the present invention, the mass of polyethylene glycol is 8-10 times that of the 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone compound.

[0054] In some embodiments of the present invention, the high weather-resistant washable macromolecular dye further includes any one or more of the following raw materials: preservative, water, and surfactant, to adjust the surface tension, viscosity, and color value of the high weather-resistant washable macromolecular dye.

[0055] In some embodiments of the present invention, the viscosity of the high weather-resistant washable macromolecular dye is ≤700mPa.s, the surface tension is required to be 20-60mN / m, and the color concentration at an absorption coefficient wavelength of 550nm is 2.4±0.15Abs / (g / L.cm).

[0056] In some embodiments of the present invention, high weather-resistant washable macromolecular dyes are used in high weather-resistant washable inks and daily chemical products.

[0057] The present invention will be further illustrated by the following examples, but these examples do not limit the scope of the invention.

[0058] When numerical ranges are given in the embodiments, it should be understood that, unless otherwise stated in the present invention, both endpoints of each numerical range and any value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in this invention have the same meaning as commonly understood by one of ordinary skill in the art. Where specific conditions are not specified in the embodiments, conventional conditions or conditions recommended by the manufacturer shall apply. All reagents or instruments whose manufacturers are not specified are conventional products that can be purchased commercially. In addition to the specific methods, equipment, and materials used in the embodiments, based on the knowledge of the prior art possessed by one of ordinary skill in the art and the description of this invention, any prior art methods, equipment, and materials similar to or equivalent to those described, used, and materials in the embodiments of this invention may be used to implement this invention.

[0059] Example 1

[0060] A highly weather-resistant, washable macromolecular dye, comprising a dye macromolecule. The preparation method of the dye macromolecule is as follows:

[0061] S1, condensation reaction (e.g.) Figure 1 (as shown)

[0062] Add 300.0g of polyethylene glycol 600 and 15g of potassium carbonate to a 500mL dry four-necked flask. Heat to 140℃ and stir for 60min. After mixing evenly, add 30.0g of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone in batches, keeping the addition time at 60min. After the addition is complete, leave the flask open and maintain this temperature for 10h.

[0063] S2, neutralization reaction:

[0064] The reaction solution in S1, at the reaction endpoint, was cooled to below 80℃ and filtered through a 200-mesh filter. The filtrate was collected, and 120g of water was added. The pH was adjusted to 7.9 with dilute sulfuric acid. After the pH stabilized, the solution was filtered again through a 300-mesh filter to obtain an aqueous solution. Based on the specified parameters, 50g of water and 2.3g of preservative were added to the aqueous solution, resulting in a UV color value of 2.40 Abs / (g / L). . A finished product of a rose-red, highly weather-resistant, washable macromolecular dye (cm).

[0065] Examples 2-7 describe the preparation of a highly weather-resistant, washable macromolecular dye using the same method as in Example 1, with the only differences being some conditions and material selection. All other operations are identical to those in Example 1. Details are as follows:

[0066] Example 2

[0067] S1, condensation reaction:

[0068] Add 240.0g of polyethylene glycol 200 and 15g of potassium carbonate to a 500mL dry four-necked flask. Heat to 140℃ and stir for 60min. After mixing evenly, add 30.0g of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone in batches, keeping the addition time at 45min. After the addition is complete, leave the flask open and maintain this temperature for 12h.

[0069] S2, neutralization reaction:

[0070] The reaction solution in S1, which has reached the reaction endpoint, is cooled to below 80℃ and filtered through a 200-mesh filter. The filtrate is collected, and 100g of water is added. The pH is adjusted to 8.0 with 30% dilute hydrochloric acid. After the pH stabilizes, the solution is filtered again through a 300-mesh filter to obtain an aqueous solution. According to the specifications, 60g of water and 2.5g of preservative are added to the aqueous solution, resulting in a UV color value of 2.45 Abs / (g / L). . A finished product of a rose-red, highly weather-resistant, washable macromolecular dye (cm).

[0071] Example 3

[0072] By replacing polyethylene glycol 600 with an equimolar amount of polyethylene glycol 400, a high weather-resistant, washable macromolecular dye with a UV color value of 2.42 Abs / (g / L.cm) was obtained.

[0073] Example 4

[0074] By replacing polyethylene glycol 600 with an equimolar amount of polyethylene glycol 800, a high weather-resistant, washable macromolecular dye with a UV color value of 2.38 Abs / (g / L.cm) was obtained.

[0075] Example 5

[0076] S1, condensation reaction:

[0077] Add 300.0g of polyethylene glycol 1000 and 15g of potassium carbonate to a 500mL dry four-necked flask. Heat to 140℃ and stir for 60min. After mixing evenly, add 30.0g of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone in batches, keeping the addition time at 45min. After the addition is complete, leave the flask open and maintain this temperature for 12h.

[0078] S2, neutralization reaction:

[0079] The reaction solution in S1, which has reached the reaction endpoint, is cooled to below 80℃ and filtered through a 200-mesh filter. The filtrate is collected, and 100g of water is added. The pH is adjusted to 8.2 with 30% dilute hydrochloric acid. After the pH stabilizes, the solution is filtered again through a 300-mesh filter to obtain an aqueous solution. According to the specifications, 50g of water and 2.5g of preservative are added to the aqueous solution to obtain a UV color value of 2.30Abs / (g / L). . A finished product of a rose-red, highly weather-resistant, washable macromolecular dye (cm).

[0080] Example 6

[0081] S1, condensation reaction:

[0082] Add 300.0g of polyethylene glycol 600 and 10g of potassium hydroxide to a 500mL dry four-necked flask. Heat to 140℃ and stir for 60min. After mixing evenly, add 30.0g of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone in batches, keeping the addition time at 60min. After the addition is complete, leave the flask open and maintain this temperature for 8h.

[0083] S2, neutralization reaction:

[0084] The reaction solution in S1, at the reaction endpoint, was cooled to below 80℃ and filtered through a 200-mesh filter. The filtrate was collected, and 120g of water was added. The pH was adjusted to 9.0 with dilute sulfuric acid. After the pH stabilized, the solution was filtered again through a 300-mesh filter to obtain an aqueous solution. According to the specifications, 55g of water and 2.3g of preservative were added to the aqueous solution, resulting in a UV color value of 2.42 Abs / (g / L). . A finished product of a rose-red, highly weather-resistant, washable macromolecular dye (cm).

[0085] Example 7

[0086] S1, condensation reaction:

[0087] Add 300.0g of polyethylene glycol 600 and 7.3g of sodium hydroxide to a 500mL dry four-necked flask. Heat to 140℃ and stir for 60min. After mixing evenly, add 30.0g of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone in batches, keeping the addition time at 60min. After the addition is complete, leave the flask open and maintain this temperature for 8h.

[0088] S2, neutralization reaction:

[0089] The reaction solution in S1, at the reaction endpoint, was cooled to below 80℃ and filtered through a 200-mesh filter. The filtrate was collected, and 120g of water was added. The pH was adjusted to 8.3 with dilute sulfuric acid. After the pH stabilized, the solution was filtered again through a 300-mesh filter to obtain an aqueous solution. According to the specifications, 50g of water and 2.3g of preservative were added to the aqueous solution, resulting in a UV color value of 2.43 Abs / (g / L). . A finished product of a rose-red, highly weather-resistant, washable macromolecular dye (cm).

[0090] Comparative Examples 1 and 2 were prepared using the same method as in Example 1, with the only differences being some conditions and material selection. All other operations were identical to those in Example 1, as detailed below:

[0091] Comparative Example 1

[0092] The S1 condensation reaction takes place at 90℃, which is very slow. Most of the raw materials remain unreacted, and the macromolecular dye appears as a light rose-red color, indicating that the reaction has failed.

[0093] Comparative Example 2

[0094] The S1 condensation reaction temperature is 170℃. The color of the macromolecular dye turns dark, and the high temperature damages the material, causing the reaction to fail.

[0095] Performance testing:

[0096] (1) The rose-red high weather-resistant washable macromolecular dye product prepared in Examples 1, 2, 5 and 7 (short for description in the table: rose-red macromolecular colorant) and commercially available rose-red pigment powder were used as raw materials to prepare rose-red colorant ink for educational use. The specific formula is shown in the table below.

[0097] Table 1 Rose Red Coloring Ink

[0098]

[0099] (2) The viscosity, pH, surface tension, UV value and writing effect of the rose-red colorant ink prepared in (1) were tested, and the results are shown in Table 2:

[0100] Table 2 Performance Test Results

[0101]

[0102] (3) The water washability test was performed on the rose-red colorant ink prepared in (1). The specific steps are as follows:

[0103] (a) Soak the six-fiber cloth in room temperature rose-red colorant ink washable color ink for 24 hours, take it out and wash it with clean water, and observe the residue.

[0104] (b) Color residue is indicated by a scale of 0-4:

[0105] 0 - No residue, meaning 100% washable;

[0106] 1. Slight residue, meaning 99% (inclusive) - 100% (exclusive) is washable;

[0107] 2. Heavier residue, meaning 95% (inclusive) to 99% (exclusive), can be washed with water;

[0108] 3. Severe residue, meaning 90% (inclusive) to 95% (exclusive) can be washed with water;

[0109] 4- Total residue, meaning less than 90% (excluding) is washable.

[0110] The test results are shown in Table 3 and Figure 2 As shown:

[0111] Table 3. Test results of washability performance

[0112]

[0113] According to Table 2, Table 3 and Figure 2It can be seen that, under similar color depth (UV value), compared with traditional pigments, the rose red colorant ink formed by the high weather-resistant and washable macromolecular dye provided in the embodiments of the present invention has significantly improved washability on six-fiber cloth. Among them, the washability of application example 2 made with Peg200 as raw material is slightly worse than that of other application examples, indicating that the lower the polyether molecular chain, the worse the washability.

[0114] II. Sunlight resistance and fragrance oxidation resistance test:

[0115] The high weather-resistant, washable macromolecular dye from Example 1 above was formulated with rose-red dyes from patents US005250708A and CN116322633A to create a rose-red daily chemical product. Then, fragrances were added for sun resistance and fragrance oxidation resistance tests. The fragrances selected were Huabao, Aipu, and Fenhao. The specific formula is as follows:

[0116] Table 4 Daily Chemical Formulas

[0117]

[0118] The performance of the aforementioned rose-red daily chemical product was tested, and the specific steps are as follows:

[0119] (1) Sunlight resistance test: Use 25mL transparent sample bottles to fill the above daily chemical products, and then place them in a xenon lamp aging test chamber for 24 hours (Shenzhen Beite Instrument Equipment Co., Ltd., model BT-SD-150A). Then judge the sunlight resistance level according to the fading. There are 8 levels in total, with level 8 being the best and level 1 being the worst.

[0120] (2) Fragrance oxidation resistance test: Use 25mL transparent sample bottles to fill the above daily chemical products respectively, place them in a constant temperature and humidity incubator (model LHS-50B) at 50℃ for 12 weeks, and observe the fading.

[0121] Table 5 Results of tests for sun resistance and fragrance oxidation resistance

[0122]

[0123] As can be seen from the test results in Table 5, the daily chemical products formed by the high weather-resistant and washable macromolecular dyes provided in this embodiment of the invention have better sun resistance and oxidation resistance.

[0124] The above embodiments are merely illustrative of the principles and effects of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by those skilled in the art without departing from the spirit and technical concept disclosed in the present invention should still be covered by the claims of the present invention.

Claims

1. A high weatherable washable macromolecular dye, characterized in that: comprise dye macromolecules having the following structural formula wherein n is 4-23.

2. The high weatherable washable macromolecular dye according to claim 1, characterized in that: The dye macromolecule is prepared by the following steps: S1, condensation reaction of 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone and polyethylene glycol under alkaline conditions to form a dye macromolecule; S2, pH adjustment of the dye macromolecule obtained in S1 to obtain a dye macromolecule.

3. The high weatherable washable macromolecular dye according to claim 2, characterized in that: The polyethylene glycol is selected from PEG200-1000.

4. The high weatherable washable macromolecular dye according to claim 3, characterized in that: The alkaline condition in S1 refers to pH≥10; the alkaline condition is obtained by adding a base selected from at least one of potassium hydroxide, potassium carbonate, triethylamine, sodium carbonate, sodium hydroxide, wherein the molar ratio of the base to 1-amino-2-bromo-4-hydroxy-9,10-anthraquinone is (1.1-2.2):

1.

5. The high weatherable washable macromolecular dye according to claim 4, characterized in that: The temperature of the condensation reaction is 100-150℃.

6. The high weatherable washable macromolecular dye according to claim 5, characterized in that: In S2, a pH regulator is used for adjustment, and the adjusted pH value is 7-10; the pH regulator is selected from one of hydrochloric acid and dilute sulfuric acid.

7. The high weatherable washable macromolecular dye according to claim 6, characterized in that: The polyethylene glycol is PEG600, and the base is potassium carbonate.

8. The high weatherable washable macromolecular dye according to claim 7, characterized in that: The temperature of the condensation reaction is 130-150℃.

9. The high weatherable washable macromolecular dye according to any one of claims 1-8, characterized in that: Also included are raw materials of any one or a combination of two or more of preservatives, water, surfactants; high weather resistance washable macromolecular dyes with viscosity ≤700 mPa . s, surface tension at 20-60 mN / m, color density at 2.4±0.15 Abs / (g / L·cm) at wavelength 550 nm.

10. Use of a high-weatherable washable macromolecular dye according to claim 9, characterized in that: Used for writing and teaching ink and daily chemical products. Used for writing and teaching ink and daily chemical products.

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