CN114316204A - Preparation method of pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye - Google Patents
Preparation method of pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye Download PDFInfo
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
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- 239000002562 thickening agent Substances 0.000 claims description 5
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
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- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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Abstract
The invention relates to a preparation method of a Congo red-aqueous polyurethane high-molecular dye-based pH color-changing textile, which comprises the following steps: preparing Congo red-aqueous polyurethane high-molecular dye; and (5) screen printing the textile. The pH color-changing waterborne polyurethane high molecular dye is used for textile printing to obtain the textile with the pH color-changing function, and the textile changes from red to blue in an environment with a pH value of less than 3, and shows remarkable pH response color-changing behavior, higher color-changing sensitivity, good reversibility and fatigue resistance.
Description
Technical Field
The invention belongs to the field of textiles, and particularly relates to a preparation method of a pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye.
Background
The pH response color-changing textile can rapidly generate obvious and reversible color change when the pH changes, thereby providing a visual signal, and being widely applied to the fields of monitoring water quality, soil protection, wound healing condition, food freshness, protective clothing indicating leakage of acid and alkali gases and the like. At present, the pH response color-changing textile is developed by applying chemical dyes with pH indication function and natural pigments to the textile through dyeing, coating, printing, surface treatment and the like. For example, chinese patent CN103590263A discloses a method for preparing pH color-changing fabric by dyeing cotton fabric with acid-induced color-changing dye, which has simple process, good color fastness and uniform coloring. Chinese patent CN106521987A reports that pH sensitive color-changing fabric prepared by printing method with natural pigment as pH indicator can display different colors under different pH, is not only fashionable and beautiful, but also can be used as a sensor. However, some pH indicators have carcinogenic sensitization and harm to human health, and do not meet the requirements of the printing and dyeing industry on the safety and environmental protection of materials.
The development of the macromolecular dye provides an effective way for solving the problems. The macromolecular dye is a colored polymer which connects a dye color body to a macromolecular main chain or a macromolecular side chain through a covalent bond. Since the dye color bodies are covalently bonded to the polymer chains, the dye color bodies are less likely to leak. Meanwhile, the macromolecular dye has large molecular size and is difficult to be absorbed by skin through a cell membrane. Research shows that many dye color bodies have low toxicity or even disappear after being introduced into a macromolecular chain, and show excellent safety and environmental protection characteristics. In addition, the macromolecular dye has excellent film forming property, migration resistance and good coloring capacity, and has wide application prospects in the fields of textiles, coatings, printing ink and the like.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of a pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye, wherein the pH color-changing aqueous polyurethane high-molecular dye is used for textile printing to obtain the textile with the pH color-changing function, and the textile changes from red to blue in an environment with a pH value of less than 3, so that the textile shows obvious pH response color-changing behavior, higher color-changing sensitivity, good reversibility and fatigue resistance.
The invention provides a preparation method of a Congo red-aqueous polyurethane high-molecular dye-based pH color-changing textile, which comprises the following steps:
(1) adding isophorone diisocyanate, polyether diol and a catalyst into a reaction system, taking tetrahydrofuran as a solvent, heating to 70-90 ℃, and reacting for 1-3 hours to obtain a polyurethane prepolymer; then adding micromolecular dihydric alcohol into a reaction system, and performing chain extension reaction for 1-3 hours at the temperature of 70-90 ℃; then directly adding Congo red, and continuously reacting for 1-3 h at 70-90 ℃; finally, carrying out rotary distillation to remove tetrahydrofuran to obtain the pH color-changing waterborne polyurethane high-molecular dye;
(2) preparing the pH color-changing waterborne polyurethane high-molecular dye into a printing dye solution, uniformly stirring, carrying out screen printing on the textile, and drying and baking to obtain the pH color-changing textile.
The mole ratio of isophorone diisocyanate, polyether diol, micromolecular diol and Congo red in the step (1) is 4: (0.5-2): (0.5-1.5): (1-6).
The polyether diol in the step (1) is polyethylene glycol or polytetrahydrofuran diol.
The catalyst in the step (1) is dibutyltin dilaurate, and the adding amount of the catalyst is 0.05-0.2% of the total mass of isophorone diisocyanate and polyether glycol.
The micromolecular dihydric alcohol in the step (1) is 1, 4-butanediol or dimethylolpropionic acid.
The printing dye solution in the step (2) comprises the following components: based on the total mass of 100%, 5-15% of pH color-changing water-based polyurethane high-molecular dye, 3-7% of thickening agent, 8-20% of adhesive and 70-80% of deionized water.
Further, the thickener is an anionic or nonionic thickener.
Furthermore, the adhesive is polyurethane, acrylate or organic silicon adhesive.
The drying temperature in the step (2) is 60-80 ℃, and the drying time is 30-60 min.
The baking temperature in the step (2) is 120-160 ℃, and the baking time is 3-5 min.
The Congo red used in the invention has amino groups and sodium sulfonate groups in the molecule, wherein the amino groups are reacted with isocyanate groups, and the sodium sulfonate groups endow the polyurethane with water solubility. Other pH indicators are mostly based on the reaction of phenolic hydroxyl groups with isocyanate groups, the phenolic hydroxyl groups being less reactive than amino groups and therefore the reaction rate is not as high as Congo Red.
Advantageous effects
According to the invention, the pH indicator Congo red is introduced into the waterborne polyurethane in a covalent bonding manner to obtain the pH color-changing waterborne polyurethane high-molecular dye. The dye color body is combined with the macromolecular chain by a covalent bond, so the dye color body is not easy to leak; meanwhile, the macromolecular dye has large molecular size and is difficult to permeate a cell membrane to be absorbed by skin, so that the safety of the Congo red dye is effectively improved. The pH color-changing waterborne polyurethane high molecular dye is used for textile printing to obtain a textile with a pH color-changing function, and the textile changes from red to blue in an environment with a pH value of less than 3, and shows remarkable pH response color-changing behavior, higher color-changing sensitivity, good reversibility and fatigue resistance.
Drawings
FIG. 1 shows the pH discoloration property of the aqueous polyurethane polymer dye solution prepared in example 1;
FIG. 2 shows the pH-responsive reversibility of color change and fatigue resistance of the aqueous polyurethane polymer dye printed fabric prepared in example 1.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
(1) Adding isophorone diisocyanate, polyethylene glycol and dibutyltin dilaurate into a reaction system, taking tetrahydrofuran as a solvent, heating to 80 ℃, and reacting for 2h to obtain a polyurethane prepolymer; then adding 1, 4-butanediol into the reaction system, and carrying out chain extension reaction for 2h at 80 ℃ (if the system becomes viscous in the reaction process, adding tetrahydrofuran to reduce viscosity); then adding Congo red directly, and continuing to react for 2h at 80 ℃; finally, carrying out rotary distillation to remove tetrahydrofuran to obtain the pH color-changing waterborne polyurethane high-molecular dye; wherein the mole ratio of isophorone diisocyanate to polyethylene glycol to 1, 4-butanediol to Congo red is 4: 2: 1: 2;
(2) preparing a pH color-changing aqueous polyurethane high-molecular dye into a printing dye solution, uniformly stirring 5% of the pH color-changing aqueous polyurethane high-molecular dye, 5% of a thickening agent, 10% of a binding agent and 80% of deionized water by taking the total mass of raw materials as 100%, carrying out screen printing on the textile, and then drying and baking to obtain the pH color-changing textile.
The pH value of the pH color-changing aqueous polyurethane high-molecular dye solution is adjusted by using 1mol/L hydrochloric acid solution, and an ultraviolet-visible light spectrophotometer (UV-1800PC type) is used for testing the ultraviolet-visible light absorption spectrum of the aqueous polyurethane high-molecular dye solution under different pH conditions, wherein the testing conditions are that the wavelength range is 250-700nm, the scanning speed is medium speed, and the testing interval is 20 nm. The printed fabric to be tested was folded twice, and the color parameters (e.g., K/S, L, a, b values) of the printed fabric and its color change at different pH were measured using a colorimeter (CE7000A model, D65 illuminant, 10 ° field), and three points were measured for each sample, and the average value was taken. To further analyze the pH-responsive reversibility of color change of printed fabrics, the printed fabrics were alternately wetted with 1mol/L HCl solution and 1mol/L NaOH solution and tested for their maximum absorption wavelength and corresponding K/S value. The results of fig. 1 and 2 and table 1 were obtained.
TABLE 1 color parameters before and after pH response discoloration of printed fabrics
As shown in FIG. 1, as the pH value decreases from 6 to 1, the absorption peak of the polymer dye at 510nm gradually decreases, and a new absorption peak appears and gradually increases around 600-655nm, and the absorption peak widens, and the color gradually changes from red to blue-violet. The reason is that under the acidic condition, the amino group in Congo red is protonated to form an azo protonated structure, and the azo protonated structure is continuously isomerized and converted into a quinoid structure, so that the conjugation degree of molecules is increased, the maximum absorption wavelength is shifted to the long-wave direction, and the color is changed into blue-violet.
As can be seen from FIG. 2, with the change of pH value, the maximum absorption wavelength of the pH-discoloration aqueous polyurethane polymer dye printed fabric is cyclically changed between 510nm and 590-610nm, the color is cyclically changed between red and blue-purple, and the color is changed to blue for about 2s, 30s is needed for recovering red, the color depth is basically kept stable after two cyclic discoloration, and excellent reversibility and fatigue resistance are presented, which indicates that the prepared polymer dye printed fabric has excellent repeated use performance.
As can be seen from Table 1, as the pH value is reduced, the maximum absorption wavelength of the original printed cotton fabric is gradually shifted from 510nm to 590nm, the corresponding K/S value is changed from 3.47 to 6.30, the brightness is reduced, the red tone is reduced, the blue tone of the cotton fabric is increased, the color component is reduced, and the printing color is changed from red to blue. In addition, the response color change of the printed fabric in the solution with the pH value below 2 only needs 1min or even 2s, and the response speed is high. Therefore, the macromolecular dye printed cotton fabric has obvious pH response behavior and higher color change sensitivity in an environment with the pH value less than 3.
Claims (8)
1. A preparation method of a pH color-changing textile based on Congo red-water-based polyurethane high-molecular dye comprises the following steps:
(1) adding isophorone diisocyanate, polyether diol and a catalyst into a reaction system, taking tetrahydrofuran as a solvent, heating to 70-90 ℃, and reacting for 1-3 hours to obtain a polyurethane prepolymer; then adding micromolecular dihydric alcohol into a reaction system, and performing chain extension reaction for 1-3 hours at the temperature of 70-90 ℃; then directly adding Congo red, and continuously reacting for 1-3 h at 70-90 ℃; finally, carrying out rotary distillation to remove tetrahydrofuran to obtain the pH color-changing waterborne polyurethane high-molecular dye;
(2) preparing the pH color-changing waterborne polyurethane high-molecular dye into a printing dye solution, uniformly stirring, carrying out screen printing on the textile, and drying and baking to obtain the pH color-changing textile.
2. The method of claim 1, wherein: the mole ratio of isophorone diisocyanate, polyether diol, micromolecular diol and Congo red in the step (1) is 4: (0.5-2): (0.5-1.5): (1-6).
3. The method of claim 1, wherein: the polyether diol in the step (1) is polyethylene glycol or polytetrahydrofuran diol.
4. The method of claim 1, wherein: the catalyst in the step (1) is dibutyltin dilaurate, and the adding amount of the catalyst is 0.05-0.2% of the total mass of isophorone diisocyanate and polyether glycol.
5. The method of claim 1, wherein: the micromolecular dihydric alcohol in the step (1) is 1, 4-butanediol or dimethylolpropionic acid.
6. The method of claim 1, wherein: the printing dye solution in the step (2) comprises the following components: based on the total mass of 100%, 5-15% of pH color-changing water-based polyurethane high-molecular dye, 3-7% of thickening agent, 8-20% of adhesive and 70-80% of deionized water.
7. The method of claim 1, wherein: the drying temperature in the step (2) is 60-80 ℃, and the drying time is 30-60 min.
8. The method of claim 1, wherein: the baking temperature in the step (2) is 120-160 ℃, and the baking time is 3-5 min.
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| CN202111463445.XA CN114316204A (en) | 2021-12-02 | 2021-12-02 | Preparation method of pH color-changing textile based on Congo red-aqueous polyurethane high-molecular dye |
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|---|---|---|---|---|
| US6162646A (en) * | 1996-04-03 | 2000-12-19 | William H. Webster | Urine pH indicator system and associated methods |
| US20040014875A1 (en) * | 2002-07-17 | 2004-01-22 | Roman Decorating Products | Color-changing wallpaper adhesive primer/activator |
| CN103590263A (en) * | 2013-11-15 | 2014-02-19 | 东华大学 | Preparation method of pH color-changing fabric |
| CN104311779A (en) * | 2014-10-11 | 2015-01-28 | 江南大学 | Synthetic method of water-based polyurethane high polymer dye |
| CN108504167A (en) * | 2018-03-20 | 2018-09-07 | 东莞市卡勒贸易有限公司 | A kind of discoloration of chance water and indiffusible ink and its preparation method and application |
| CN108623785A (en) * | 2018-05-08 | 2018-10-09 | 安徽建筑大学 | A kind of aqueous polyurethane acidity macromolecule indicator and preparation method thereof |
| CN109852135A (en) * | 2017-11-30 | 2019-06-07 | 金永昌 | According to PH change and change colour laminated film and include the paper diaper of the laminated film |
-
2021
- 2021-12-02 CN CN202111463445.XA patent/CN114316204A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6162646A (en) * | 1996-04-03 | 2000-12-19 | William H. Webster | Urine pH indicator system and associated methods |
| US20040014875A1 (en) * | 2002-07-17 | 2004-01-22 | Roman Decorating Products | Color-changing wallpaper adhesive primer/activator |
| CN103590263A (en) * | 2013-11-15 | 2014-02-19 | 东华大学 | Preparation method of pH color-changing fabric |
| CN104311779A (en) * | 2014-10-11 | 2015-01-28 | 江南大学 | Synthetic method of water-based polyurethane high polymer dye |
| CN109852135A (en) * | 2017-11-30 | 2019-06-07 | 金永昌 | According to PH change and change colour laminated film and include the paper diaper of the laminated film |
| CN108504167A (en) * | 2018-03-20 | 2018-09-07 | 东莞市卡勒贸易有限公司 | A kind of discoloration of chance water and indiffusible ink and its preparation method and application |
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