CN109400816B - Ultraviolet-curable color-changing gel resin and synthesis method thereof, and color changing and fading method of gel - Google Patents
Ultraviolet-curable color-changing gel resin and synthesis method thereof, and color changing and fading method of gel Download PDFInfo
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- CN109400816B CN109400816B CN201810971778.5A CN201810971778A CN109400816B CN 109400816 B CN109400816 B CN 109400816B CN 201810971778 A CN201810971778 A CN 201810971778A CN 109400816 B CN109400816 B CN 109400816B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
- C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
- C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
Abstract
The invention discloses ultraviolet-curable color-changing gel resin and a synthesis method thereof, and a color changing and fading method of gel, and relates to color-changing gel and a synthesis method thereof, and a color changing and fading method. The invention aims to solve the technical problems of slow gelling speed and long gelling time of the existing sol-gel preparation method of the color-changing gel. The color-changing gel resin is prepared from 1 polyvinyl alcohol, amino acid, a catalyst, a modifier, a photoactive monomer, a photoinitiator and a solvent. Adding polyvinyl alcohol into a solvent, carrying out a grafting reaction with amino acid, then sequentially adding a catalyst and a modifier, dialyzing, and then adding a photoinitiator and an optically active monomer to obtain the ultraviolet-curable color-changing gel resin. The resin can be cured into gel by ultraviolet irradiation, the gel can change color by soaking in metal ion solution, and can fade by soaking in fading solution, and can be used as false packaging material.
Description
Technical Field
The invention relates to a color-changing gel, a synthesis method thereof and a color changing and fading method.
Background
The color-changing material is a substance that changes color with changes in external environmental conditions. The color-changing materials can be classified into photochromic, electrochromic, thermochromic, acid-base photochromic, wet-color, pressure-photochromic, and the like, according to the factors causing the color change. That is to say, the color-changing material has the characteristics that the structure can be reversibly changed along with different illumination intensities, different temperatures of atmospheric environments, different atmospheric humidity, different pressures and the like, so that the reversible change of the visible light absorption spectrum and the reversible change of the color can be caused. As an intelligent color developing material, the material has wide application, such as thermosensitive recording materials, temperature indicating materials and the like of instruments. In addition, the color-changing material has a plurality of applications in the high and new technical field, such as playing an important role in military camouflage and the like.
The color-changing gel is an emerging color-changing material and has all the characteristics of the color-changing material. The existing color-changing gel comprises electrochromic gel, thermochromic gel and the like, and the preparation method is a sol-gel method, but the preparation method needs long time and has slow gel speed.
Disclosure of Invention
The invention aims to solve the technical problems of slow gelling speed and long gelling time of the existing sol-gel preparation method of the color-changing gel, and provides the color-changing gel resin capable of being cured by ultraviolet light, a synthesis method thereof and a color changing and fading method of the gel.
The ultraviolet-curable color-changing gel resin is prepared from 100 parts of polyvinyl alcohol (PVA), 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent according to parts by mass.
The preparation method of the ultraviolet-curable color-changing gel resin comprises the following steps:
weighing 100 parts of polyvinyl alcohol (PVA), 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent according to the mass part ratio;
adding PVA and a solvent into a reactor, stirring for 3-5 hours at the temperature of 50-70 ℃, and then standing for 12-24 hours at room temperature to obtain a PVA dispersion liquid;
adding concentrated sulfuric acid into the PVA dispersion liquid to adjust the pH value to 3-4, then heating to 115-120 ℃, adding amino acid, and stirring for 6-10 hours; then cooling to 45-50 ℃ to obtain PVA dispersion liquid of grafted aminocarboxylic acid;
fourthly, adding 1-2 mol/L sodium hydroxide solution into the PVA dispersion liquid grafted with the aminocarboxylic acid to adjust the pH value to 6-7, then adding a catalyst, and uniformly stirring to obtain a dispersion liquid A;
fifthly, adding a modifier into the dispersion liquid A, uniformly stirring, heating to 55-60 ℃, and continuously stirring for 5-10 hours to obtain a dispersion liquid B;
sixthly, dialyzing the dispersion liquid B for 48-72 hours by using a Mv500 dialysis bag to obtain dispersion liquid C;
and seventhly, adding a photoinitiator and an optically active monomer into the dispersion liquid C, and uniformly stirring to obtain the ultraviolet-curable color-changing gel resin.
The color-changing gel resin can be solidified into gel after being irradiated by ultraviolet light for 10 seconds.
The color changing method of the gel comprises the following steps: and soaking the gel in a chromogenic metal ion solution to change the color.
The fading method of the gel is as follows: firstly, mixing a hydrochloric acid solution with the concentration of 1-1.2 mol/L and a saturated ammonium triacetate solution according to the volume ratio of 1: (3.5-4) to obtain a fading liquid; and soaking the discolored gel in fading liquid to fade.
The invention takes polyvinyl alcohol as a main chain material, achieves the purpose of color development by grafting aminocarboxylic acid functional groups on the main chain of the polyvinyl alcohol and chelation between the aminocarboxylic acid functional groups and color development metal cations, and then grafts unsaturated active double bonds on the main chain of the polyvinyl alcohol so as to ensure that the unsaturated active double bonds can carry out ultraviolet curing reaction with a cross-linking agent and a photoinitiator.
The ultraviolet-curable color-changing gel resin can realize color change by soaking in a metal ion solution such as copper ions, cobalt ions or iron ions for 10-30 s, and has high response speed and stable color development. The discolored gel can be faded after being soaked in the fading liquid for 8-10 minutes. The color development and the color fading can be alternately performed.
The color-changing gel resin of the color-changing gel resin has low cost and simple preparation method, and the color-changing gel can be applied to camouflage materials.
Drawings
Fig. 1 is a photograph of the uv-curable color-changing gel resin prepared in example 1 after photo-curing;
FIG. 2 is a photograph of the color-changeable gel resin prepared in example 1 after being soaked in a cupric chloride solution for color change;
FIG. 3 is a photo of the UV-curable color-changing gel resin prepared in example 2 after photo-curing;
FIG. 4 CoCl treated color-changing gel resin prepared in example 23And soaking the color-changed photo in the solution.
Detailed Description
The first embodiment is as follows: the ultraviolet-curable color-changing gel resin is prepared from 100 parts of polyvinyl alcohol (PVA), 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent according to parts by mass.
The second embodiment is as follows: this embodiment differs from the first embodiment in that the amino acid is glutamic acid, lysine, aspartic acid or arginine; the rest is the same as the first embodiment.
The third concrete implementation mode: this embodiment differs from the first or second embodiment in that the catalyst is N-dimethylaminopyridine, pyridine or dicyclohexylcarbodiimide; the others are the same as in the first or second embodiment.
The fourth concrete implementation mode: this embodiment is different from one of the first to third embodiments in that the modifier is maleic anhydride, acryloyl chloride, or methacrylate; the rest is the same as one of the first to third embodiments.
The fifth concrete implementation mode: this embodiment differs from one of the first to fourth embodiments in that the photoactive monomer is N, N-methylenebisacrylamide, allyl methacrylate, diallyl itaconate, or ethylene glycol dimethacrylate; the rest is the same as one of the first to fourth embodiments.
The sixth specific implementation mode: the difference between this embodiment and one of the first to fifth embodiments is that the photoinitiator is one or a mixture of two of a photoinitiator 1173, a photoinitiator TPO-L and a photoinitiator 819; the rest is the same as one of the first to fifth embodiments.
The seventh embodiment: this embodiment is different from one of the first to sixth embodiments in that the solvent is dimethyl sulfoxide, N-dimethylformamide, or dimethyl adipate; the rest is the same as one of the first to sixth embodiments.
The specific implementation mode is eight: the preparation method of the ultraviolet light curable color-changing gel resin according to the first embodiment comprises the following steps:
weighing 100 parts of polyvinyl alcohol (PVA), 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent according to the mass part ratio;
adding PVA and a solvent into a reactor, stirring for 3-5 hours at the temperature of 50-70 ℃, and then standing for 12-24 hours at room temperature to obtain a PVA dispersion liquid;
adding concentrated sulfuric acid into the PVA dispersion liquid to adjust the pH value to 3-4, then heating to 115-120 ℃, adding amino acid, and stirring for 6-10 hours; then cooling to 45-50 ℃ to obtain PVA dispersion liquid of grafted aminocarboxylic acid;
fourthly, adding 1-2 mol/L sodium hydroxide solution into the PVA dispersion liquid grafted with the aminocarboxylic acid to adjust the pH value to 6-7, then adding a catalyst, and uniformly stirring to obtain a dispersion liquid A;
fifthly, adding a modifier into the dispersion liquid A, uniformly stirring, heating to 55-60 ℃, and continuously stirring for 5-10 hours to obtain a dispersion liquid B;
sixthly, dialyzing the dispersion liquid B for 48-72 hours by using a Mv500 dialysis bag to obtain dispersion liquid C;
and seventhly, adding a photoinitiator and an optically active monomer into the dispersion liquid C, and uniformly stirring to obtain the ultraviolet-curable color-changing gel resin.
The specific implementation method nine: the difference between the embodiment and the eighth embodiment is that the stirring speed in the second step is 300-500 r/min; the rest is the same as the embodiment eight.
The detailed implementation mode is ten: the difference between the eighth embodiment and the ninth embodiment is that in the third step, the stirring speed is 300-500 r/min; the others are the same as the embodiments eight or nine.
The concrete implementation mode eleven: the difference between this embodiment and the eighth to tenth embodiments is that the stirring speed in the fourth step is 300 to 500r/min, and the stirring time is 10 to 20 min; the others are the same as the eighth to the tenth embodiments.
The specific implementation mode twelve: the difference between the eighth embodiment and the eleventh embodiment is that in the fifth embodiment, the stirring speed is 300-500 r/min, and the stirring time is 10-20 min; the others are the same as in one of the eighth to eleventh embodiments.
The specific implementation mode is thirteen: the difference between the eighth embodiment and the twelfth embodiment is that in the seventh embodiment, the stirring speed is 300-500 r/min, and the stirring time is 5-10 min; the rest is the same as the eighth to twelfth embodiments.
The specific implementation mode is fourteen: after the ultraviolet light curable color-changing gel resin is cured into gel, the color-changing method of the gel is to soak the gel in the color-developing metal ion solution, so that the color can be changed.
In the curing of the embodiment, the ultraviolet-curable color-changing gel resin can be cured by being irradiated by ultraviolet light for 10 seconds to obtain gel.
The concrete implementation mode is fifteen: the fourteenth embodiment is different from the fourteenth embodiment in that the concentration of the metal ion solution is 0.1 to 0.5 mol/L; the rest is the same as the embodiment fourteen.
The specific implementation mode is sixteen: the fourteenth or fifteenth difference from the present embodiment is that the metal ion solution is a copper ion solution, a cobalt ion solution, or an iron ion solution; the other is the same as the embodiment fourteen or fifteen.
Seventeenth embodiment: the difference between the present embodiment and the fourteenth to sixteenth embodiment is that the soaking time is 10 to 30 seconds; the others are the same as in one of the fourteenth to the sixteenth embodiments.
The specific implementation mode is eighteen: the fading method of the gel of the present embodiment is: firstly, mixing a hydrochloric acid solution with the concentration of 1-1.2 mol/L and a saturated ammonium triacetate solution according to the volume ratio of 1: (3.5-4) to obtain a fading liquid; and soaking the discolored gel in fading liquid to fade.
The detailed embodiment is nineteen: the difference between the embodiment and the specific embodiment is that the soaking time is 8-10 min; eighteen the same as the embodiment.
The beneficial effects of the present invention are verified by the following examples:
example 1: the preparation method of the ultraviolet curable color-changing gel resin of the embodiment comprises the following steps:
weighing 100 parts of polyvinyl alcohol (PVA), 50 parts of glutamic acid, 0.8 part of catalyst N-dimethylaminopyridine, 16 parts of modifier maleic anhydride, 5 parts of photoactive monomer N, N-methylene-bisacrylamide, 3 parts of photoinitiator 1173 and 1300 parts of solvent dimethyl sulfoxide according to the mass parts;
adding PVA and dimethyl sulfoxide into a reactor, heating by adopting an oil bath, stirring for 5 hours at the stirring speed of 400r/min under the condition that the temperature is 60 ℃, and then standing for 18 hours at room temperature to obtain PVA dispersion liquid;
thirdly, adding concentrated sulfuric acid into the PVA dispersion liquid to adjust the pH value to 4, then heating to 118 ℃, adding glutamic acid, and stirring for 10 hours at a stirring speed of 400 r/min; then, cooling to 50 ℃ to obtain PVA dispersion liquid of grafted aminocarboxylic acid;
fourthly, adding 2mol/L sodium hydroxide solution into the PVA dispersion liquid grafted with the aminocarboxylic acid to adjust the pH value to 6.5, then adding a catalyst N-dimethylaminopyridine, and stirring at a stirring speed of 400r/min for 10min to obtain a dispersion liquid A;
fifthly, adding maleic anhydride as a modifier into the dispersion liquid A, stirring for 10min at a stirring speed of 400r/min, then heating to 60 ℃, and continuing stirring for 5h at the stirring speed of 400r/min to obtain a dispersion liquid B;
sixthly, dialyzing the dispersion liquid B for 48 hours by using a dialysis bag with Mv500 to obtain dispersion liquid C;
seventhly, adding a photoinitiator 1173 and an optically active monomer N, N-methylene bisacrylamide into the dispersion liquid C, and stirring at the stirring speed of 300r/min for 10min to obtain the ultraviolet-curable color-changing gel resin.
The ultraviolet-curable color-changing gel resin prepared by the embodiment is irradiated for 10s by 365nm ultraviolet light to obtain gel, the curing speed of the resin is high, and the curing can be completed within about 10 s. The photograph of the gel is shown in FIG. 1.
The gel obtained after curing was immersed in a copper chloride solution having a concentration of 0.5mol/L for 30 seconds and then taken out, and it was observed that the gel was uniformly changed into blue, and the photograph thereof is shown in FIG. 2, and the RGB values thereof were 153, 172, and 150. Thus, the gel was found to change color at a high speed.
Firstly, mixing a hydrochloric acid solution with the concentration of 1mol/L and a saturated ammonium triacetate solution according to the volume ratio of 2: 7 to obtain fading liquid; and soaking the gel with changed color in a fading liquid, directly observing the color change of the gel, and after soaking for 8min, completely fading the gel to be transparent, namely realizing the fading of the gel.
The gel obtained after curing was immersed in CoCl at a concentration of 0.5mol/L3After 30 seconds of the solution, the gel was observed to turn red. Immersing the gel after color change into a 1mol/L hydrochloric acid solution and a saturated ammonium triacetate solution according to the volume ratio of 2: 7, directly observing the color change of the gel in the fading liquid mixed by 7, and after soaking for 7min, completely fading the gel to be transparent, namely realizing the fading of the gel.
Example 2: the preparation method of the ultraviolet curable color-changing gel resin of the embodiment comprises the following steps:
weighing 100 parts of polyvinyl alcohol (PVA), 40 parts of glutamic acid, 0.64 part of catalyst N-dimethylaminopyridine, 25 parts of modifier maleic anhydride, 3 parts of photoactive monomer N, N-methylene-bisacrylamide, 5 parts of photoinitiator 1173 and 1300 parts of solvent dimethyl sulfoxide according to the mass parts;
adding PVA and dimethyl sulfoxide into a reactor, heating by adopting an oil bath, stirring for 5 hours at the stirring speed of 400r/min under the condition that the temperature is 60 ℃, and then standing for 18 hours at room temperature to obtain PVA dispersion liquid;
thirdly, adding concentrated sulfuric acid into the PVA dispersion liquid to adjust the pH value to 4, then heating to 118 ℃, adding glutamic acid, and stirring for 10 hours at a stirring speed of 400 r/min; then, cooling to 50 ℃ to obtain PVA dispersion liquid of grafted aminocarboxylic acid;
fourthly, adding 2mol/L sodium hydroxide solution into the PVA dispersion liquid grafted with the aminocarboxylic acid to adjust the pH value to 6.5, then adding a catalyst N-dimethylaminopyridine, and stirring at a stirring speed of 400r/min for 10min to obtain a dispersion liquid A;
fifthly, adding maleic anhydride as a modifier into the dispersion liquid A, stirring for 10min at a stirring speed of 400r/min, then heating to 60 ℃, and continuing stirring for 5h at the stirring speed of 400r/min to obtain a dispersion liquid B;
sixthly, dialyzing the dispersion liquid B for 48 hours by using a dialysis bag with Mv500 to obtain dispersion liquid C;
seventhly, adding a photoinitiator 1173 and an optically active monomer N, N-methylene bisacrylamide into the dispersion liquid C, and stirring at the stirring speed of 300r/min for 10min to obtain the ultraviolet-curable color-changing gel resin.
The ultraviolet-curable color-changing gel resin prepared by the embodiment is irradiated for 10s by 365nm ultraviolet light to obtain gel, the curing speed of the resin is high, and the curing can be completed within about 10 s. The photograph of the gel is shown in FIG. 3.
The gel obtained after curing was immersed in a copper chloride solution having a concentration of 0.5mol/L for 30 seconds and then taken out, and it was observed that the gel turned blue. Thus, the gel was found to change color at a high speed. Immersing the gel after color change into a 1mol/L hydrochloric acid solution and a saturated ammonium triacetate solution according to the volume ratio of 2: 7, directly observing the color change of the gel in the fading liquid mixed by the two components, and after soaking for 8min, completely fading the gel to be transparent, namely realizing the fading of the gel.
Immersing the gel obtained after curing into a solution having a concentration of0.5mol/L CoCl3After 30 seconds of the solution, the gel was observed to turn uniformly red, and the photographs are shown in FIG. 4, which have RGB values of 201, 166, and 146. Immersing the gel after color change into 1mol/L hydrochloric acid solution and saturated ammonium triacetate solution according to the volume ratio of 2: 7, directly observing the color change of the gel in the fading liquid mixed by the two components, and after soaking for 8min, completely fading the gel to be transparent, namely realizing the fading of the gel.
Claims (7)
1. The ultraviolet-curable color-changing gel resin is characterized by being prepared from 100 parts of polyvinyl alcohol, 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent in parts by mass; the modifier is maleic anhydride; the photoactive monomer is N, N-methylene bisacrylamide; the photoinitiator is a photoinitiator 1173.
2. The UV-curable color-changing gel resin according to claim 1, wherein the amino acid is glutamic acid, lysine, aspartic acid or arginine.
3. The ultraviolet-curable color-changing gel resin according to claim 1 or 2, wherein the catalyst is N-dimethylaminopyridine, pyridine or dicyclohexylcarbodiimide.
4. The uv-curable color-changing gel resin according to claim 1 or 2, wherein the solvent is dimethyl sulfoxide, N-dimethylformamide or dimethyl adipate.
5. A preparation method of a discoloring gel resin capable of being cured by ultraviolet light is characterized by comprising the following steps:
weighing 100 parts of polyvinyl alcohol, 30-50 parts of amino acid, 0.5-1 part of catalyst, 15-50 parts of modifier, 1-5 parts of photoactive monomer, 1-5 parts of photoinitiator and 1000-1300 parts of solvent according to the mass parts; the modifier is maleic anhydride; the photoactive monomer is N, N-methylene bisacrylamide; the photoinitiator is a photoinitiator 1173;
adding PVA and a solvent into a reactor, stirring for 3-5 hours at the temperature of 50-70 ℃, and then standing for 12-24 hours at room temperature to obtain a PVA dispersion liquid;
adding concentrated sulfuric acid into the PVA dispersion liquid to adjust the pH value to 3-4, then heating to 115-120 ℃, adding amino acid, and stirring for 6-10 hours; then cooling to 45-50 ℃ to obtain PVA dispersion liquid of grafted aminocarboxylic acid;
fourthly, adding 1-2 mol/L sodium hydroxide solution into the PVA dispersion liquid grafted with the aminocarboxylic acid to adjust the pH value to 6-7, then adding a catalyst, and uniformly stirring to obtain a dispersion liquid A;
fifthly, adding a modifier into the dispersion liquid A, uniformly stirring, heating to 55-60 ℃, and continuously stirring for 5-10 hours to obtain a dispersion liquid B;
sixthly, dialyzing the dispersion liquid B for 48-72 hours by using a Mv500 dialysis bag to obtain dispersion liquid C;
and seventhly, adding a photoinitiator and an optically active monomer into the dispersion liquid C, and uniformly stirring to obtain the ultraviolet-curable color-changing gel resin.
6. The method of changing color of a UV-curable color-changing gel according to claim 1, wherein the gel according to claim 1 is soaked in a color-developing metal ion solution to change color.
7. A method of fading a uv curable color-changing gel according to claim 1, characterized in that the method comprises: firstly, mixing a hydrochloric acid solution with the concentration of 1-1.2 mol/L and a saturated ammonium triacetate solution according to the volume ratio of 1: (3.5-4) to obtain a fading liquid; and soaking the discolored gel in fading liquid to fade.
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