CN120082012A - A self-repairable film with high mechanical properties and its preparation method and application - Google Patents
A self-repairable film with high mechanical properties and its preparation method and application Download PDFInfo
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
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Abstract
本发明涉及一种可自修复高机械性能薄膜及其制备方法和应用，其包括以下步骤：将脲基嘧啶酮、扩链剂加入溶剂中得到混合液，将所述混合液加入聚氨酯预聚体中反应，干燥，即得可自修复高机械性能薄膜。本发明通过在聚合物内部引入含有氢键的UPy制得可自修复高机械性能薄膜，可以通过调整脲基嘧啶酮UPy含量从而调整氢键密度，使复合材料具有优秀的自愈性；并且引入密度氢键，构建物理交联网络，可以显著提升复合材料的机械性能。
The present invention relates to a self-repairable high mechanical performance film and a preparation method and application thereof, which comprises the following steps: adding ureidopyrimidone and a chain extender to a solvent to obtain a mixed solution, adding the mixed solution to a polyurethane prepolymer for reaction, and drying to obtain a self-repairable high mechanical performance film. The present invention prepares a self-repairable high mechanical performance film by introducing UPy containing hydrogen bonds inside the polymer, and can adjust the hydrogen bond density by adjusting the ureidopyrimidone UPy content, so that the composite material has excellent self-healing properties; and introducing dense hydrogen bonds to construct a physical cross-linking network can significantly improve the mechanical properties of the composite material.
Description
Technical Field
The invention relates to the technical field of self-healing materials, in particular to a self-repairable high mechanical property film, a preparation method and application thereof.
Background
Self-healing of polymers can be categorized into foreign-type healing and intrinsic-type self-healing. The self-healing material for external assistance is mainly characterized in that the repair of a damaged area is realized by the rupture of microcapsules which are embedded in the material or the coating in advance. The process is that when the matrix is broken, the microcapsule is broken to release the healing agent, and the healing agent contacts with the catalyst buried in the matrix to initiate polymerization, thereby repairing the broken part. Because the capsule is easy to manufacture, simple to process and easy to realize industrialization, the capsule is also more popular in polymer research. However, when the restorative agent is consumed, the microcapsules no longer have a healing function and can cause voids in the matrix, affecting a range of properties of the material. The intrinsic self-healing material realizes the self-healing of the damage by depending on the chemical structure and the property of the body. The self-repair is completed by breaking and reconnecting a reversible covalent bond or a reversible non-covalent bond, wherein the covalent bond mainly comprises a reversible disulfide bond, a reversible boric acid ester bond, a Diels-Alder reaction and the like, and the non-covalent bond mainly comprises a reversible hydrogen bond, pi-pi stacking, an ionic bond, a metal coordination bond and the like. Compared with the external self-healing material, the intrinsic self-healing material has the advantages of more healing means, repeatability, no need of additional catalyst, mild condition and the like, so that most of the current researches on the self-healing material are intrinsic self-healing.
The self-repairing material can effectively recover the original stability and functions after being damaged, can repair physical damage, prolongs the service life of products, reduces maintenance cost, and has important significance for sustainable development and environmental protection. However, the current method for realizing self-healing by adding a functional carrier in the material or on the surface is limited by the number of times of self-healing. Second, many self-healing materials exhibit rapid self-healing ability by building disulfide bonds, but tend to have lower mechanical strength.
Disclosure of Invention
Based on the above, the invention aims to provide a self-repairable high mechanical property film, a preparation method and application thereof, wherein the self-repairable high mechanical property film has good self-healing property and excellent mechanical property.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
The invention provides a preparation method of a self-repairable high mechanical property film, which is characterized by comprising the following steps of adding ureido pyrimidinone and a chain extender into a solvent to obtain a mixed solution, adding the mixed solution into a polyurethane prepolymer for reaction, and drying to obtain the self-repairable high mechanical property film.
As a further improvement of the scheme of the invention, the content of the ureido pyrimidinone in the self-repairable high mechanical property film is 3wt% to 5.4wt%.
As a further improvement of the scheme, the preparation method of the allopyrimidinone comprises the steps of heating and refluxing a mixture of 2-acetylbutyrolactone, guanidine carbonate, triethylamine and absolute ethyl alcohol, filtering after the solution turns yellow and turbid, washing, adjusting pH to be neutral, and carrying out post-treatment to obtain the allopyrimidinone.
As a further improvement of the scheme, the molar ratio of the 2-acetylbutyrolactone to the guanidine carbonate is 1:1, and the volume ratio of the triethylamine to the absolute ethyl alcohol is 1:4, wherein the triethylamine is used as a base catalyst and an acid neutralizer, and the absolute ethyl alcohol is used as a solvent, a temperature control medium and a side reaction inhibitor;
And/or, the heating reflux is reflux at 70-85 ℃ for 10-12h;
and/or, the pH is adjusted to be neutral by adding hydrochloric acid solution to adjust the pH to be 6-7.
As a further improvement of the scheme, the preparation method of the polyurethane prepolymer comprises the steps of dissolving glycol in a solvent, adding diisocyanate and a catalyst for reaction, and obtaining the polyurethane prepolymer.
As a further improvement of the above-described embodiment of the invention, the diol is polytetrahydrofuran having an average relative molecular mass of 850 g/mol;
and/or, the diisocyanate is isophorone diisocyanate;
and/or, the catalyst is dibutyl tin dilaurate;
and/or the solvent is N-N dimethylformamide;
And/or, the reaction is carried out at 70 ℃ to 85 ℃ for 1.5 to 2.5 hours;
and/or the volume ratio of the diol to the solvent is 1:2, and the molar ratio of the diol to the diisocyanate is 1:1.5.
As a further improvement of the above-described aspect of the present invention, the solvent is N-N dimethylformamide;
and/or the chain extender is 1, 4-butanediol;
And/or the reaction is carried out at 70-85 ℃ for 1.5-2.5h.
The invention also provides a self-repairable high mechanical property film which is prepared by adopting the preparation method.
The invention also provides application of the self-repairable high mechanical property film prepared by the preparation method in packaging of flexible electronic devices, electronic equipment shells and screens, intelligent sensors and actuators, and bionic and soft robots.
Compared with the prior art, the invention has the following beneficial effects:
1. The self-repairable high mechanical property film is prepared by introducing the allopyrimidinone UPy containing the hydrogen bond into the polymer, the hydrogen bond density can be adjusted by adjusting the content of the allopyrimidinone UPy, the prepared self-repairable high mechanical property film has a certain rheological property, so that the self-repairable high mechanical property film has excellent self-healing property, and a physical crosslinking network is constructed by introducing the density hydrogen bond, so that the mechanical property of the composite material can be obviously improved, and the prepared film not only has quick self-healing capability, but also has excellent mechanical property.
2. The method is simple to operate, the raw materials are simple and easy to obtain, the tensile strength of the prepared self-repairable high-mechanical-property film reaches 17.6MPa, the toughness can reach 75.6MJm -3, the toughness is improved by 91% compared with that of pure polyurethane, the mechanical properties of the self-repairable high-mechanical-property film can be completely recovered after self-healing for 1h at 80 ℃, and the prepared film has good self-healing property and excellent mechanical properties and has wide application prospect in the field of high-strength and high-toughness self-healing materials.
Drawings
FIG. 1 is an infrared spectrum of UPy prepared in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of UPy obtained in example 1;
FIG. 3 is an infrared spectrum of a pure PU and PUUPy composite material prepared in example 1;
FIG. 4 is a drawing showing the stretch of PUUPy composite made in example 1;
FIG. 5 is a stress-strain curve of PUUPy composites prepared in examples 1-4;
FIG. 6 is a flow chart of the self-healing after shearing and performing a tensile test for PUUPy composites prepared in example 1;
FIG. 7 is an optical photograph of the self-healing process of PUUPy composites prepared in example 1;
FIG. 8 is a stress-strain curve of PUUPy composite material prepared in example 1 before and after self-healing.
Detailed Description
In order that the invention may be readily understood, a more particular description of the invention will be rendered by reference to specific embodiments that are illustrated below. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, 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 belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
Example 1
The embodiment provides a self-repairable high mechanical property film, and the preparation method comprises the following steps:
(1) Synthesis of ureidopyrimidinones
A mixture of 6.4g of 2-acetylbutyrolactone, 9g of guanidine carbonate, 16mL of triethylamine and 65mL of absolute ethanol was refluxed at 80℃for 12h, the solution turned yellow and turbid, then filtered, washed several times with ethanol, the solid was dispersed in deionized water, the excess triethylamine was neutralized with hydrochloric acid solution, and the pH was adjusted to 6-7. Finally, filtering, alternately washing with deionized water and ethanol, and drying to obtain the ureido pyrimidinone UPy.
(2) Preparation of polyurethane prepolymers
In a three-necked flask with nitrogen gas, dried Polytetrahydrofuran (PTMEG) (8.5 g,10 mmol) was dissolved in 10mL of N-N Dimethylformamide (DMF) and heated to 70℃and then isophorone diisocyanate (IPDI) (3.33 g,15 mmol) and dibutyltin dilaurate (DBTDL, 0.025 g) as a catalyst were added and reacted at 70℃for 2 hours to give a polyurethane prepolymer PU. In this step, it should be noted that the polytetrahydrofuran is dried and nitrogen is introduced into the three-necked flask to provide an anhydrous environment for preparing the polyurethane prepolymer, and the side reaction is prevented, and the reaction temperature is not too high, otherwise the reaction is too fast and solidification is caused.
(3) Preparation of self-repairable high mechanical film
3.75Mmol of allopyrimidinone UPy (0.634 g) prepared in the step (1) and 1.25mmol of 1, 4-butanediol (BDO, 0.1125 g) are mixed into 10mL of DMF solution to obtain a mixed solution, the mixed solution is added into the polyurethane prepolymer solution prepared in the step (2) and the reaction is continued for 2 hours at 70 ℃ to obtain a self-repairing high mechanical property film PUUPy (wherein UPy content is 5 wt%), which is marked as PUUPy 5. Finally, the PUUPy composite material is dried in an 80 ℃ oven for 12 hours and in a 60 ℃ vacuum oven for 24 hours.
FIG. 1 is an infrared spectrum of UPy obtained in step (1) of the present example, and it can be seen from FIG. 1 that the peak at 3379cm -1 corresponds to the stretching vibration of the-OH group, the peak at 1641cm -1 is caused by the C=O double bond in the isopropylidene ring, the absorption peak at 3118cm -1 is related to the N-H bond on the isopropylidene ring, the stretching vibration peak at 1603cm -1 belongs to the C=N bond in the isopropylidene ring, and the stretching vibration peak at 1049cm -1 belongs to the C-O bond, demonstrating successful synthesis of UPy of the present example.
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of UPy obtained in step (1) of this example, further demonstrating the successful synthesis of UPy of this example.
FIG. 3 is an infrared spectrum of the polyurethane prepolymer PU prepared in step (2) and the self-repairable high mechanical property film PUUPy prepared in step (3) of the present example, wherein the carbonyl peak intensity at 1695cm -1 is increased, indicating that the molecular bond hydrogen bond interaction is enhanced.
With reference to FIG. 4, the self-repairable high mechanical property film PUUPy prepared in the step (3) of this example was subjected to a stretching test using an Shimadzu electronic universal tester at a stretching rate of 1cm/min under a tensile force of 2000N, and the result showed that it could be stretched to 10 times the original length, and had excellent stretching properties.
Example 2
The same embodiment as in example 1 was adopted, and the difference from example 1 was that in step (3) of this example, the amount of allopyrimidinone UPy was 2.5mmol (0.423 g), the amount of 1, 4-butanediol was 2.5mmol (0.225 g), and the UPy content in the finally obtained self-repairable high mechanical property film PUUPy was 3wt%, which was designated PUUPy 3.
Example 3
The same embodiment as in example 1 was adopted, and the difference from example 1 was that in step (3) of this example, the amount of UPy was 3.33mmol (0.563 g), the amount of 1, 4-butanediol was 1.67mmol (0.15 g), and the resulting self-repairable high mechanical properties film PUUPy had a UPy content of 4wt%, which was PUUPy 4.
Example 4
The same embodiment as in example 1 was adopted, and the difference from example 1 was that in step (3) of this example, the amount of UPy was 4mmol (0.676 g), the amount of 1, 4-butanediol was 1mmol (0.09 g), and the resulting self-repairable high mechanical properties film PUUPy.4 wt% of UPy was PUUPy 5.4.
Test case
A tensile test was performed on the self-repairable high mechanical property film PUUPy prepared in examples 1-4 using an Shimadzu electronic universal tester at a tensile force of 2000N at a tensile rate of 1cm/min to give a stress strain curve as shown in FIG. 5 (the toughness of the material can be evaluated by the area under the stress strain curve), which shows that the tensile strength of PUUPy 5 prepared in example 1 reached 17.6MPa, the toughness reached 75.6MJ m -3, 91.6% higher than pure PU, the tensile strength of PUUPy 3 prepared in example 2 reached 16.2MPa, but only 53.1MJ m -3, the tensile strength of PUUPy 4 prepared in example 3 reached 16.2MPa, but only 65.5MJ m -3, and the tensile strength of PUUPy 5.4 prepared in example 4 reached 19.9MPa, but only 61.4MJ m -3. From this, it can be seen that PUUPy 5 prepared in example 1 has the best mechanical properties, the tensile strength is increased by 2MPa, while the self-repairable high mechanical properties films prepared in examples 2-3 have poor mechanical properties, because too low UPy content makes the composite material unable to construct enough density hydrogen bonds, unable to form an effective physical cross-linking network, resulting in poor mechanical properties, while in example 4 too high UPy content makes the composite material generate too much density hydrogen bonds inside, resulting in excessive physical cross-linking, resulting in the composite material having very high tensile strength but lower toughness.
In order to further verify the self-healing performance of the self-healing high mechanical performance film, the self-healing tensile test is carried out on the PUUPy composite material prepared in the embodiment 1, and the tensile test is carried out by shearing the PUUPy composite material prepared in the embodiment 1 in half, then self-healing for 1h at 80 ℃, shooting the self-healing process by using a microscope, the result is shown in fig. 7, and then carrying out the tensile test by using an Shimadzu electronic universal tester under the tensile force of 2000N, wherein the tensile rate is 1cm/min, and the stress-strain curve shown in fig. 8 is obtained. The result shows that after self-healing for 1h at 80 ℃, the tensile strength of the PUUPy composite material prepared in the example 1 reaches an initial state, and the mechanical properties are completely recovered, so that the self-repairable high-mechanical-property film has self-healing properties.
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (9)
1. A preparation method of a self-repairable film with high mechanical properties is characterized by comprising the following steps of adding ureido pyrimidinone and a chain extender into a solvent to obtain a mixed solution, adding the mixed solution into a polyurethane prepolymer for reaction, and drying to obtain the self-repairable film with high mechanical properties.
2. The method for preparing a self-repairable high mechanical property film according to claim 1, wherein the content of the ureido pyrimidinone in the self-repairable high mechanical property film is 3wt% to 5.4wt%.
3. The preparation method of the self-repairable high mechanical property film according to claim 1, wherein the preparation method of the ureido pyrimidinone comprises the steps of heating and refluxing a mixture of 2-acetyl butyrolactone, guanidine carbonate, triethylamine and absolute ethyl alcohol, filtering after the solution turns yellow and turbid, washing, adjusting pH to be neutral, and performing post-treatment to obtain the ureido pyrimidinone.
4. The method for preparing a self-healing high mechanical property film according to claim 2, wherein the molar ratio of 2-acetylbutyrolactone to guanidine carbonate is 1:1, and the volume ratio of triethylamine to absolute ethanol is 1:4;
And/or, the heating reflux is reflux at 70-85 ℃ for 10-12h;
and/or, the pH is adjusted to be neutral by adding hydrochloric acid solution to adjust the pH to be 6-7.
5. The preparation method of the self-repairable high mechanical property film according to claim 1, wherein the preparation method of the polyurethane prepolymer is characterized in that glycol is dissolved in a solvent, diisocyanate and a catalyst are added for reaction, and the polyurethane prepolymer is obtained.
6. The method for producing a self-healing high mechanical properties film according to claim 5, wherein the glycol is polytetrahydrofuran having an average relative molecular mass of 850 g/mol;
and/or, the diisocyanate is isophorone diisocyanate;
and/or, the catalyst is dibutyl tin dilaurate;
and/or the solvent is N-N dimethylformamide;
And/or, the reaction is carried out at 70 ℃ to 85 ℃ for 1.5 to 2.5 hours;
and/or the volume ratio of the diol to the solvent is 1:2, and the molar ratio of the diol to the diisocyanate is 1:1.5.
7. The method for preparing a self-healing high mechanical property film according to claim 1, wherein the solvent is N-N dimethylformamide;
and/or the chain extender is 1, 4-butanediol;
And/or the reaction is carried out at 70-85 ℃ for 1.5-2.5h.
8. A self-healing high mechanical properties film prepared by the method of any one of claims 1-7.
9. Use of a self-repairable high mechanical property film prepared by the method of any one of claims 1-7 in packaging of flexible electronic devices, electronic equipment housings and screens, intelligent sensors and actuators, biomimetics and soft robots.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120842654A (en) * | 2025-09-18 | 2025-10-28 | 扬州博恒新能源材料科技有限公司 | Optical film with self-repairing function and preparation method thereof |
| CN120978225A (en) * | 2025-10-20 | 2025-11-18 | 浙江晶科储能有限公司 | Secondary batteries and their preparation methods, battery devices, power consumption devices and energy storage devices |
| CN120988463A (en) * | 2025-10-22 | 2025-11-21 | 内蒙古工业大学 | A method for preparing modified graphene oxide polyurethane composite material |
| CN120988463B (en) * | 2025-10-22 | 2026-05-01 | 内蒙古工业大学 | A method for preparing modified graphene oxide polyurethane composite material |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120842654A (en) * | 2025-09-18 | 2025-10-28 | 扬州博恒新能源材料科技有限公司 | Optical film with self-repairing function and preparation method thereof |
| CN120978225A (en) * | 2025-10-20 | 2025-11-18 | 浙江晶科储能有限公司 | Secondary batteries and their preparation methods, battery devices, power consumption devices and energy storage devices |
| CN120988463A (en) * | 2025-10-22 | 2025-11-21 | 内蒙古工业大学 | A method for preparing modified graphene oxide polyurethane composite material |
| CN120988463B (en) * | 2025-10-22 | 2026-05-01 | 内蒙古工业大学 | A method for preparing modified graphene oxide polyurethane composite material |
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