CN111253520A - Polymerizable eutectic solvent for self-repairing material, conductive elastomer and preparation method - Google Patents
Polymerizable eutectic solvent for self-repairing material, conductive elastomer and preparation method Download PDFInfo
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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Abstract
The invention discloses a polymerizable eutectic solvent for a self-repairing material, a conductive elastomer and a preparation method of the conductive elastomer, wherein the polymerizable eutectic solvent is obtained by reacting a hydrogen bond acceptor and a hydrogen bond donor at 60-100 ℃, the hydrogen bond donor comprises a carboxylic acid monomer containing double bonds and an acrylamide monomer, the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1:1, the molar ratio of the acrylamide monomer to the carboxylic acid monomer containing double bonds is not less than 1:1, and the self-repairing conductive elastomer comprises the polymerizable eutectic solvent, a cross-linking agent and an initiator. The self-repairing conductive elastomer prepared by using the eutectic solvent has transparent appearance, good conductivity, excellent self-repairing performance at minus 30-60 ℃ and good environmental stability, and does not need to add a conductive nano material in the preparation process.
Description
Technical Field
The invention relates to the field of ionic liquid, in particular to a polymerizable eutectic solvent for a self-repairing material, a conductive elastomer and a preparation method thereof.
Background
The eutectic solvent is a subset of ionic liquid, has the characteristics of low cost, low toxicity, 100% atomic utilization rate in the preparation process, environmental friendliness and the like on the basis of inheriting the advantages of low vapor pressure, non-aqueous biocompatibility, non-flammability, chemical stability, high dissolving capacity and the like of the ionic liquid, and is expected to replace the ionic liquid in the future. At present, eutectic solvents are mainly applied to aspects such as carbon dioxide capture, metal oxide dissolution, drug dissolution and purification, catalysts, electrodeposition, material preparation, biopolymer treatment and the like. However, relatively few reports of polymerizable eutectic solvents in the preparation of polymers exist in the current research, and no report exists at present that the polymerizable eutectic solvents can be directly used for preparing self-repairing elastomers.
The high-transparency, stretchable, conductive and fast self-repairing elastomer material has strong plasticity, and particularly has a very large application space in the fields of conductive electrodes, brakes, sensors, speakers, flexible display films and the like. In recent years, the rapid development of flexible electronic products capable of bending and stretching has made higher demands on transparency, stretchability, conductivity, transparency, flexibility, stretching property, conductivity and self-repairing property under various environments of the fast self-repairing elastomer. The currently reported method for preparing the self-repairing conductive material generally adopts a method for compounding flexible polymers (such as Polyurethane (PU), polydimethylsiloxane and the like (PDMS) with nano conductive particles (such as polypyrrole, PEDOT: PSS, graphene, carbon nanotubes and the like), but the method has a large defect, and firstly, the transparency of the self-repairing material is greatly reduced due to the addition of the nano conductive particles in the preparation process, so that the use of the self-repairing material is limited; secondly, most of the existing researches are focused on the exploration of self-repairing conductive hydrogel, but the ionic gel elastomer containing no moisture is little involved, and as is known, the mechanical property of the hydrogel is poor, and the performance is reduced because the hydrogel cannot keep the moisture in the natural environment; thirdly, the preparation process of the current self-repairing material is complex, mostly involves the use of organic solvent, has high cost and plays a certain role in limiting the development of the self-repairing material. Therefore, a novel self-repairing material needs to be explored, which can ensure high light transmittance, conductivity, high tensile property and rapid self-repairing performance, and can realize lower cost and better environmental stability.
Disclosure of Invention
Based on the above, the present invention provides a polymerizable eutectic solvent for self-repairing materials, which overcomes the defects of the prior art.
Another object of the present invention is to provide a self-healing conductive elastomer. The self-repairing conductive elastomer prepared by the invention has high light transmittance, conductivity, high tensile property and rapid self-repairing property, and the self-repairing capability is excellent at minus 30 ℃ to 60 ℃.
The invention also aims to provide a preparation method of the self-repairing conductive elastomer.
The technical scheme is as follows:
the polymerizable eutectic solvent for the self-repairing material is obtained by reacting a hydrogen bond acceptor and a hydrogen bond donor at 60-100 ℃, wherein the hydrogen bond donor comprises a carboxylic acid monomer containing double bonds and an acrylamide monomer, the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1:1, and the molar ratio of the acrylamide monomer to the carboxylic acid monomer containing double bonds is not less than 1: 1.
The inventor finds out through experiments that when the hydrogen bond donor is a double-bond-containing carboxylic acid monomer and an acrylamide monomer, the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1:1, and the molar ratio of the acrylamide monomer to the double-bond-containing carboxylic acid monomer is not less than 1:1, the polymerizable eutectic solvent prepared from the hydrogen bond acceptor and the hydrogen bond donor can be used for preparing a material with a self-repairing function, and the material can be cured under the action of an initiator to obtain a transparent elastomer which has a self-repairing function. According to the self-repairing material, whether the polymerizable eutectic solvent capable of being used for preparing the self-repairing material can be formed or not is important in the molar ratio of the acrylamide monomer, the double-bond carboxylic acid monomer and the hydrogen bond acceptor, if the dosage of the hydrogen bond donor or the hydrogen bond acceptor is not proper, the eutectic solvent is difficult to form, and if the ratio of the acrylamide monomer and the double-bond carboxylic acid monomer is not proper, the self-repairing function is absent.
In one embodiment, the molar ratio of the hydrogen bond acceptor to the double bond-containing carboxylic acid monomer and the acrylamide monomer is 2:1: 1-2: 1: 5.
In one embodiment, the carboxylic acid monomer containing double bonds is one or more of acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, and aconitic acid.
In one embodiment, the carboxylic acid monomer containing double bond is acrylic acid or maleic acid.
In one embodiment, the acrylamide monomer is acrylamide, methacrylamide, diacetone acrylamide, N-isopropylacrylamide, N-hydroxyethyl acrylamide, N-dimethylacrylamide, N-methylolacrylamide.
In one embodiment, the acrylamide-based monomer is acrylamide.
In one embodiment, the hydrogen bond acceptor is one or more of choline chloride, anhydrous betaine, monohydrate betaine, ammonium chloride, methyl triphenyl phosphonium bromide, benzyl triphenyl phosphonium chloride, N-diethyl ethanolammonium chloride, and the like.
A self-healing conductive elastomer comprising: the self-repairing material comprises a polymerizable eutectic solvent, a cross-linking agent and an initiator, wherein the molar ratio of the cross-linking agent to a hydrogen bond donor is 0.5: 100-5: 100; the amount of the initiator is 0.5-5% of the total mass of the polymerizable eutectic solvent and the cross-linking agent, and the cross-linking agent is a multifunctional acrylate monomer or resin.
The eutectic solvent and the cross-linking agent are mixed to prepare the self-repairing conductive elastomer, the conductive nano material is not required to be added in the preparation process, the flexibility of the self-repairing conductive elastomer can be further improved by adding a proper amount of the cross-linking agent, and the obtained self-repairing conductive elastomer is transparent in appearance, good in conductivity, excellent in self-repairing performance and good in environmental stability.
In one embodiment, the cross-linking agent is one or more of tripropylene glycol diacrylate, polyethylene glycol diacrylate, dipropylene glycol diacrylate, 1, 6-hexanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate phthalate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, and the like.
In one embodiment, the initiator is a thermal initiator or a photoinitiator.
In one embodiment, the photoinitiator is one or more of benzoin and derivatives photoinitiator, alkyl benzophenone photoinitiator, acylphosphorus oxide photoinitiator, and more specifically, the benzoin and derivatives photoinitiator may be benzoin, benzoin dimethyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, etc. the benzoin initiator may be diphenylethanone, α -dimethoxy- α -phenylacetophenone, etc., the alkyl benzophenone may be α -diethoxyacetophenone, α -hydroxyalkylphenone, α -aminoalkylbenzophenone, etc. the acylphosphorus oxide may be aroylphosphine oxide, bisbenzoylphenylphosphine oxide, etc. more specifically, the photoinitiator may be one of TPO 3 (2-hydroxy-2-methyl-1-phenylpropanone), 184 (1-hydroxycyclohexylphenylketone), TPO-L (2,4, 6-trimethylbenzoylphenylphosphine oxide ethyl ester), 819 (2, 6-phenylbenzoyl-2-methyl-1-phenylpropiophenone), 292-L (2,4, 6-trimethylethoxyphenylphosphine oxide), DW (2-hydroxy-2' - (2-hydroxyethoxyphenyl-phenyl-propanone), etc.
The thermal initiator is an organic peroxide initiator or an azo initiator. Specifically, the organic peroxide initiator is one or more of benzoyl peroxide, lauroyl peroxide, cumene hydroperoxide, tert-butyl hydroperoxide, di-tert-butyl peroxide, dicumyl peroxide, tert-butyl peroxybenzoate and tert-butyl peroxypivalate. The azo initiator is azobisisobutyronitrile or azobisisoheptonitrile.
The preparation method of the self-repairing conductive elastomer comprises the following steps:
s1, preparing a polymerizable eutectic solvent: reacting the hydrogen bond acceptor and the hydrogen bond donor at 60-100 ℃ for 3-5 h to obtain a clear and transparent polymerizable eutectic solvent;
s2, preparing a conductive elastomer prepolymer mixed solution: uniformly mixing a cross-linking agent, an initiator and the polymerizable eutectic solvent, and stirring for 1-3 h to obtain a conductive elastomer prepolymer mixed solution;
s3, preparing the self-repairing conductive elastomer: and (4) pouring the conductive elastomer prepolymer mixed solution obtained in the step S2 into a vessel, and curing or thermally curing under ultraviolet light irradiation to obtain the self-repairing conductive elastomer.
In one embodiment, the curing energy of the ultraviolet light is 2 Kw.
In one embodiment, the ultraviolet light is cured for 5min to 30 min.
The invention has the beneficial effects that: according to the invention, by researching and screening the hydrogen bond donor, the polymerizable eutectic solvent capable of being used for preparing the self-repairing material can be obtained when a carboxylic acid monomer containing double bonds and an acrylamide monomer are selected as the hydrogen bond donor and matched with a hydrogen bond acceptor according to a specific proportion; the polymerizable eutectic solvent, the cross-linking agent and the initiator are mixed according to a specific proportion, so that the conductive elastomer with the self-repairing function can be obtained, the obtained conductive elastomer has high light transmittance, better conductivity, stretchability, flexibility and excellent self-repairing performance, has excellent self-repairing capability at the temperature of-30-60 ℃, and the self-repairing conductive elastomer has the advantages of good environmental stability, simple preparation method, less pollution and low cost.
Drawings
FIG. 1 is a comparison of the self-healing conductive elastomer of example 15 placed on a sheet of school identification paper.
FIG. 2 is a graph illustrating a self-healing capability test of the self-healing conductive elastomer of example 15.
FIG. 3 is a graph illustrating conductivity testing of a self-healing conductive elastomer according to example 15.
FIG. 4 is a stress-strain graph of the self-healing conductive elastomers of examples 15-19.
FIG. 5 is a thermogram of differential scanning calorimetry of the self-healing conductive elastomer of example 15.
FIG. 6 is an appearance of the self-healing conductive elastomer of example 15 after freezing for 7 days.
FIG. 7 is a graph of stress-strain curves of the self-healing conductive elastomer of example 15 before and after freezing.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to the accompanying drawings and the detailed description. It should be understood that the detailed description and specific examples, while indicating the scope of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
The glass transition temperature of the polymerizable eutectic solvent was-104.2 ℃ as measured by differential scanning calorimetry.
Example 2
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 3.6g of hydrogen bond donor acrylic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at the temperature of 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 3
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 4.3g of hydrogen bond donor methacrylic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at the temperature of 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 4
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 6.5g of hydrogen bond donor citraconic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted at 60 ℃ for 4 hours to obtain a clear and transparent polymerizable eutectic solvent.
Example 5
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: stirring and reacting 13.96g of hydrogen bond acceptor choline chloride, 8.7g of hydrogen bond donor aconitic acid and 3.554g of hydrogen bond donor acrylamide at 60 ℃ for 4h to obtain a clear and transparent polymerizable eutectic solvent.
Example 6
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 4.25g of hydrogen bond donor methacrylamide are stirred and reacted for 4 hours at the temperature of 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 7
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 8.45g of hydrogen bond donor diacetone acrylamide are stirred and reacted for 4 hours at the temperature of 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 8
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 5.65g of hydrogen bond donor N-isopropylacrylamide are stirred and reacted at 60 ℃ for 4 hours to obtain a clear and transparent polymerizable eutectic solvent.
Example 9
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 5.75g of hydrogen bond donor N-hydroxyethyl acrylamide are stirred and reacted for 4 hours at the temperature of 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 10
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 4.95g of hydrogen bond donor N, N-dimethylacrylamide are stirred and reacted at 60 ℃ for 4 hours to obtain a clear and transparent polymerizable eutectic solvent.
Example 11
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: stirring 25.7g of hydrogen bond acceptor methyl triphenyl phosphonium bromide, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide at 60 ℃ for reacting for 4 hours to obtain a clear and transparent polymerizable eutectic solvent.
Example 12
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 5.35g of hydrogen bond acceptor ammonium chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 13
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 7.108g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
Example 14
The polymerizable eutectic solvent for the self-repairing material is prepared by the following steps: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 17.77g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
To the eutectic solvent prepared in examples 1 to 10, 12 and 13 was added 0.25g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropiophenone, stirred for 2 hours, mixed well, poured into a teflon petri dish (radius 3cm), and cured under ultraviolet light (2Kw) for 5min to obtain an elastomer having a transparent appearance. To the eutectic solvent prepared in example 11 and example 14 was added 0.35g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methylpropiophenone, stirred for 2h, mixed well, poured into a teflon petri dish (radius 3cm), and cured under ultraviolet light (2Kw) for 5min to give an elastomer with a transparent appearance.
The elastomer obtained above was cut with a blade, cut into two pieces, and then the two pieces were put together and taken out to observe the elastomer. As a result, it was found that the elastomers obtained by irradiating the eutectic solvents prepared in examples 1 to 14 with an initiator and ultraviolet light adhered together immediately after cutting, and the joint was cracked, but the two elastomers were not separated. Therefore, the polymerizable eutectic solvents disclosed in the embodiments 1-14 have a fast self-repairing capability after being cured, and can be used for preparing self-repairing materials.
Example 15
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.17g of polyethylene glycol diacrylate, 0.23g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 16
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.34g of polyethylene glycol diacrylate, 0.24g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the self-repairing conductive elastomer is obtained.
Example 17
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.51g of polyethylene glycol diacrylate, 0.24g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 18
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.68g of polyethylene glycol diacrylate, 0.24g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 19
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 7.108g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.17g of polyethylene glycol diacrylate, 0.27g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 20
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: and uniformly mixing 0.21g of neopentyl glycol diacrylate, 0.23g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent, and stirring for reacting for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 21
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 1.2g of dipropylene glycol diacrylate, 0.74g of 2-hydroxy-2-methyl-1-phenyl acetone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
Example 22
A self-repairing conductive elastomer is prepared by the following steps:
s1, preparing a polymerizable eutectic solvent: 13.96g of hydrogen bond acceptor choline chloride, 5.8035g of hydrogen bond donor maleic acid and 3.554g of hydrogen bond donor acrylamide are stirred and reacted for 4 hours at 60 ℃ to obtain a clear and transparent polymerizable eutectic solvent.
S2, preparing a conductive elastomer prepolymer mixed solution: 0.17g of polyethylene glycol diacrylate, 1.15g of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and the eutectic solvent are uniformly mixed, and stirred to react for 2 hours to obtain a transparent conductive elastomer prepolymer mixed solution.
S3, preparing the self-repairing conductive elastomer: and 4.83g of the transparent conductive elastomer prepolymer mixed solution obtained in the step S2 is poured into a polytetrafluoroethylene culture dish (with the radius of 3cm), and is cured for 5min under ultraviolet light (2Kw), so that the transparent self-repairing conductive elastomer is obtained.
In the invention, the transparent round elastic bodies (transparent appearance and elasticity) can be prepared in the embodiments 15 to 22, the patterns of the school emblems can be clearly seen when the round elastic bodies are placed on the drawing sheets of the school emblems (university of southern China), the transparency of the round elastic bodies is extremely high, and fig. 1 is a comparison chart of the self-repairing conductive elastic bodies prepared in the embodiment 15 and placed on the drawing sheets of the school emblems.
The self-repairing conductive elastomers prepared in the embodiments 15 to 22 were cut with a blade into 2 pieces, and then the 2 pieces of self-repairing conductive elastomers after cutting were pieced together, and the experimental results showed that the 2 pieced-together self-repairing conductive elastomers would stick together by themselves, and would not break when stretched after standing for a period of time, and after standing for 48 hours, the mechanical properties were comparable to those of the raw materials. FIG. 2 is a graph illustrating a self-healing capability test of the self-healing conductive elastomer of example 15, and FIG. 2a is a graph illustrating the self-healing conductive elastomer prepared in example 15; FIG. 2b is a schematic representation of 2 separate self-healing conductive elastomers resulting from cutting the self-healing conductive elastomer; fig. 2c is a state of the self-repairing conductive elastomer when 2 separate self-repairing conductive elastomers are pieced together, and then the stand horse grips one of the self-repairing conductive elastomers with tweezers and suspends the other self-repairing conductive elastomer; fig. 2d is a state of the self-repairing conductive elastomer when 2 spliced self-repairing conductive elastomers are placed still for 48 hours, and then two tweezers are used for respectively clamping two sides of the self-repairing conductive elastomer and pulling the self-repairing conductive elastomer.
The self-repairing conductive elastomers prepared in the embodiments 15 to 22 are cut into long strips, two ends of the self-repairing conductive elastomers are connected with the conducting wires, the small electric bulbs are installed on the conducting wires, and the bulbs are electrified to emit light, which shows that the self-repairing conductive elastomers prepared by the invention have conductive performance, the brightness of the bulbs can be slightly darkened when the long strip self-repairing conductive elastomers are stretched, the bulbs still emit light, and the brightness of the bulbs is lightened after the bulbs are rebounded, which shows that the self-repairing conductive elastomers can realize flexible stretching, and the self-repairing conductive elastomers still have conductive performance in the. FIG. 3 is a graph illustrating conductivity testing of a self-healing conductive elastomer according to example 15.
The self-healing conductive elastomers prepared in examples 15-19 were subjected to a stress-strain test, and the stress-strain curves are shown in FIG. 4. As can be seen from FIG. 4, the self-repairing conductive elastomer prepared by the method is an elastomer with better rebound elasticity.
Differential scanning calorimetry analysis is carried out on the self-repairing conductive elastomer described in the embodiment 15, a curve chart is shown in fig. 5, and it can be seen from fig. 5 that the glass transition temperature of the self-repairing conductive elastomer obtained in the embodiment is-98.6 ℃, so that the self-repairing conductive elastomer disclosed by the invention can keep a high elastic state at a very low temperature, and a molecular chain can move in a wide temperature range and can self-repair at a low temperature.
In order to further examine the repair capability of the self-repairing conductive elastomer at low temperature, the self-repairing conductive elastomer prepared by the method in example 15 is cut into two pieces, then the 2 pieces of the cut self-repairing conductive elastomer are put into a refrigerator freezing layer at the temperature of-25 ℃ to-23 ℃ after being spliced together and frozen for 7 days, and then the two pieces of the cut self-repairing conductive elastomer are taken out after 7 days, and are bonded together, and the crack is not obvious, as shown in fig. 6. The stress-strain test is carried out on the self-repairing conductive elastomer, as shown in fig. 7, the test shows that the stress-strain curve of the self-repairing conductive elastomer after being frozen for 7 days is substantially the same as that of the original self-repairing conductive elastomer, which indicates that the self-repairing conductive elastomer prepared by the invention still has good self-repairing capability at extremely low temperature, and the mechanical property after self-repairing is equivalent to that of the raw material.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. The polymerizable eutectic solvent for the self-repairing material is characterized by being obtained by reacting a hydrogen bond acceptor and a hydrogen bond donor at the temperature of 60-100 ℃, wherein the hydrogen bond donor comprises a carboxylic acid monomer containing double bonds and an acrylamide monomer, the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1:1, and the molar ratio of the acrylamide monomer to the carboxylic acid monomer containing double bonds is not less than 1: 1.
2. The polymerizable eutectic solvent for the self-repairing material of claim 1, wherein the molar ratio of the hydrogen bond acceptor to the double bond-containing carboxylic acid monomer to the acrylamide monomer is 2:1: 1-2: 1: 5.
3. The polymerizable eutectic solvent for self-repairing materials according to claim 1, wherein the carboxylic acid monomer containing double bonds is one or more of acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid and aconitic acid.
4. The polymerizable eutectic solvent for self-repairing materials according to claim 3, wherein the carboxylic acid monomer containing a double bond is acrylic acid or maleic acid.
5. The polymerizable eutectic solvent for self-repairing materials of claim 1, wherein the acrylamide monomer is acrylamide, methacrylamide, diacetone acrylamide, N-isopropyl acrylamide, N-hydroxyethyl acrylamide, N-dimethyl acrylamide, N-hydroxymethyl acrylamide.
6. The polymerizable eutectic solvent for self-repairing materials according to claim 5, wherein the acrylamide monomer is acrylamide.
7. The polymerizable eutectic solvent for self-repairing materials as claimed in claim 1, wherein the hydrogen bond acceptor is one or more of choline chloride, anhydrous betaine, betaine monohydrate, ammonium chloride, methyl triphenyl phosphonium bromide, benzyl triphenyl phosphonium chloride, N-diethyl ethanol ammonium chloride, and the like.
8. A self-healing conductive elastomer, comprising: the self-repairing material comprises a polymerizable eutectic solvent, a cross-linking agent and an initiator, wherein the molar ratio of the cross-linking agent to a hydrogen bond donor is 0.5: 100-5: 100; the amount of the initiator is 0.5-5% of the total mass of the polymerizable eutectic solvent and the cross-linking agent, and the cross-linking agent is a multifunctional acrylate monomer or resin.
9. The self-healing conductive elastomer of claim 8, wherein the initiator is a thermal initiator or a photoinitiator.
10. The method for preparing the self-repairing conductive elastomer as claimed in claim 8 or 9, which is characterized by comprising the following steps:
s1, preparing a polymerizable eutectic solvent: reacting the hydrogen bond acceptor and the hydrogen bond donor at 60-100 ℃ for 3-5 h to obtain a clear and transparent polymerizable eutectic solvent;
s2, preparing a conductive elastomer prepolymer mixed solution: uniformly mixing a cross-linking agent, an initiator and the polymerizable eutectic solvent, and stirring for 1-3 h to obtain a conductive elastomer prepolymer mixed solution;
s3, preparing the self-repairing conductive elastomer: and (4) pouring the conductive elastomer prepolymer mixed solution obtained in the step S2 into a vessel, and curing or thermally curing under ultraviolet light irradiation to obtain the self-repairing conductive elastomer.
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| PCT/CN2019/108315 WO2020114049A1 (en) | 2018-12-03 | 2019-09-26 | Polymerizable deep eutectic solvent for self-repairing materials, electrically conductive elastomer, and preparation method thereof |
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| CN116200843B (en) * | 2023-01-09 | 2024-05-17 | 华南理工大学 | Preparation method of optical self-healing flexible optical fiber, optical self-healing flexible optical fiber and application thereof |
| CN116217980A (en) * | 2023-03-16 | 2023-06-06 | 四川大学 | Eutectoid gel with biosensing performance and antibacterial effect and preparation method thereof |
| CN116285454A (en) * | 2023-03-22 | 2023-06-23 | 中南大学 | Polymerizable monomer eutectic solvent, adhesive obtained by polymerization of polymerizable monomer eutectic solvent and preparation method of adhesive |
| CN116496436A (en) * | 2023-04-28 | 2023-07-28 | 西安理工大学 | Preparation method and application of multi-hydrogen bond network-based self-repairing high-transparency conductive elastomer |
| CN117700624A (en) * | 2024-02-06 | 2024-03-15 | 广东工业大学 | Super-adhesion damping material based on super-molecular deep eutectic solution and preparation method thereof |
| CN117700624B (en) * | 2024-02-06 | 2024-04-12 | 广东工业大学 | Super-adhesion damping material based on super-molecular deep eutectic solution and preparation method thereof |
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| WO2020114049A1 (en) | 2020-06-11 |
| CN111253520B (en) | 2021-07-02 |
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