CN114437484B - Semi-crystalline ionic gel and preparation method and application thereof - Google Patents
Semi-crystalline ionic gel and preparation method and application thereof Download PDFInfo
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/097—Sulfur containing compounds
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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
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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- G01V—GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS
- G01V3/00—Electric or magnetic prospecting or detecting; Measuring magnetic field characteristics of the earth, e.g. declination, deviation
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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
- C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/08—Homopolymers or copolymers of acrylic acid esters
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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
- C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
Abstract
The application provides a semi-crystalline ionic gel and a preparation method and application thereof. The semi-crystalline ionic gel consists of a semi-crystalline polymer and an ionic liquid loaded in the semi-crystalline polymer. A method for preparing a semicrystalline ionic gel comprising: mixing raw materials including a monomer compound, a cross-linking agent and an initiator, reacting to obtain the semi-crystalline polymer, and then soaking the semi-crystalline polymer in the ionic liquid to obtain the semi-crystalline ionic gel; the monomer compound includes a hydrophobic ionic liquid monomer and an ionophilic liquid monomer. Application of semi-crystalline ionic gel in sensor and actuator. The semi-crystalline ionic gel provided by the application can be used for sensors and actuators, and has a shape memory function so as to realize repeated recycling of materials.
Description
Technical Field
The application relates to the field of new materials, in particular to a semicrystalline ionic gel and a preparation method and application thereof.
Background
The ionic gel is an ionic conductor material formed by a polymer network and an ionic liquid, and has the advantages of high ionic conductivity, wide electrochemical stability window, nonflammability, nonvolatility, transparency, good thermal stability and chemical stability, stretchability and the like. The rapid development of ionic gel materials, such as "electronic skin", with sensory, sensory and skin-like mechanical properties is enabled by the designability of the component parts.
At present, most of ionic conductor materials are still mainly based on single or soft or hard mechanical properties, and the hardness and softness of the materials can be changed at different temperatures by selection and design of ionic liquid in a very small number of ionic gel materials, so that the application of ionic gel is greatly limited.
Disclosure of Invention
The present application aims to provide a semicrystalline ionic gel, a preparation method and an application thereof, so as to solve the above problems.
In order to achieve the purpose, the following technical scheme is adopted in the application:
a semi-crystalline ionic gel is composed of a semi-crystalline polymer and an ionic liquid loaded in the semi-crystalline polymer.
The application also provides a preparation method of the semicrystalline ionic gel, which comprises the following steps:
mixing raw materials including a monomer compound, a cross-linking agent and an initiator, reacting to obtain the semi-crystalline polymer, and then soaking the semi-crystalline polymer in the ionic liquid to obtain the semi-crystalline ionic gel;
the monomer compound includes a hydrophobic liquid monomer and an ionophilic liquid monomer.
Preferably, the hydrophobic and ionic liquid monomer comprises one or more of C15-C25 alkyl acrylate compounds, C15-C25 vinyl compounds, C15-C25 styrene compounds, C15-C25 alkyl methacrylate compounds and C15-C25 acrylamide compounds.
Preferably, the ionic-philic liquid monomer comprises a C1-C5 alkyl acrylate compound, a C1-C5 vinyl compound, a C1-C5 styrene compound, a C1-C5 alkyl methacrylate compound and a C15-C25 acrylamide compound.
Preferably, the initiator comprises one or more of a photoinitiator, a thermal initiator, a redox initiator;
preferably, the photoinitiator comprises one or more of 2,4,6 (trimethylbenzoyl) diphenylphosphine oxide, 2,4, -trimethylbenzoylphosphonic acid ethyl ester, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholino-1-propanone, 2-isopropylthioxanthone, 4-dimethylamino-benzoic acid ethyl ester, 1-hydroxy-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, benzoin dimethyl ether, methyl o-benzoylbenzoate, 4-chlorobenzophenone, 4-phenylbenzophenone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone;
preferably, the thermal initiator comprises one or more of azoisobutyronitrile, 4' -azo (4-cyanovaleric acid), azobisisobutyronitrile hydrochloride, benzoyl peroxide;
preferably, the redox initiator comprises one or more of hydrogen peroxide/ferrous salts, amine peroxodisulfate/tetramethylethylenediamine, potassium peroxodisulfate/sodium sulfite, dibenzoyl peroxide/N, N-dimethylaniline.
Preferably, the crosslinking agent comprises one or more of a polyfunctional acrylic crosslinking agent, a polyfunctional styrenic crosslinking agent, a polyfunctional vinyl crosslinking agent, and a polyfunctional acrylamide crosslinking agent;
preferably, the multifunctional acrylic crosslinker comprises one or more of poly (ethylene glycol) diacrylate, poly (ethylene glycol) methyl diacrylate, 1, 3-propanediol diacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediol diacrylate;
preferably, the multifunctional acrylamide-based crosslinking agent comprises methylene bisacrylamide;
preferably, the multifunctional styrenic crosslinker comprises divinylbenzene;
preferably, the polyfunctional vinyl-based crosslinking agent comprises diethylene glycol divinyl ether.
Preferably, the ionic liquid comprises one or more of quaternary ammonium salt ionic liquid, imidazole ionic liquid and quaternary phosphonium ionic liquid;
preferably, the quaternary ammonium salt ionic liquid comprises tributylmethylammonium bistrifluoromethanesulfonylimide salt;
preferably, the imidazole ionic liquid comprises 1-methyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-ethyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-propyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-butyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-methyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-methyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole hexafluorophosphate, 1-butyl-3-methylimidazole hexafluorophosphate, 1-methyl-3-methylimidazole chloride, 1-ethyl-3-methylimidazole chloride, 1-butyl-3-methylimidazole chloride, 1-methyl-3-methylimidazole bromide, 1-ethyl-3-methylimidazole bromide, 1-butyl-3-methylimidazole bromide, 1-methyl-3-methylimidazole perchlorate, 1-ethyl-3-methylimidazole perchlorate, 1-butyl-3-methylimidazole 1-trifluoromethylimidazole perchlorate, 1-butyl-3-methylimidazole perchlorate, 1-methyl-3-methylimidazole 3-trifluoromethylimidazole perchlorate, 1-butyl-3-methylimidazole perchlorate, 1-methyl-3-methylimidazole sulfonate, 1-methyl-3-methylimidazole perchlorate, 1-butyl-3-methylimidazole-methyl-3-methyl imidazole perchlorate, 1-methyl imidazole, one or more of 1-ethyl-3-methylimidazole trifluoroacetate or 1-butyl-3-methylimidazole trifluoroacetate;
preferably, the quaternary phosphonium based ionic liquid comprises tetrabutylphosphonium bistrifluoromethane sulphonimide salt and/or tributylethylphosphonbistrifluoromethane sulphonimide salt.
Preferably, the mass ratio of the monomer compound, the initiator, the cross-linking agent and the ionic liquid is 1: (0.0001-0.05): (0.0001-0.1): (0.1-20);
preferably, the mass ratio of the semicrystalline polymer to the ionic liquid is 1: (0.01-10).
Preferably, the reaction comprises one or more of a photoinitiated reaction, a thermally initiated reaction and a redox initiated reaction;
preferably, the condition of the photoinitiated reaction is that the power density of a light source is 1mW/cm 2 -1000mW/cm 2 The wavelength is 200nm-450nm, and the time is 0.01h-24h;
preferably, the conditions of the thermal initiation reaction are 60-80 ℃ and 2-24 h;
preferably, the redox initiation reaction is carried out at the temperature of 0-40 ℃ for 2-24 h.
Preferably, degassing under vacuum condition for 1min-30min is further included after the mixing and before the reaction;
preferably, the method further comprises the following steps after the reaction and before the soaking: degassing the reaction product for 18-24 h under the conditions of vacuum state and 40-50 ℃.
The application also provides an application of the semi-crystalline ionic gel, which is used for sensors and actuators.
Compared with the prior art, the beneficial effect of this application includes:
the semi-crystalline ionic gel provided by the application consists of a semi-crystalline polymer network matrix and ionic liquid, wherein the polymer network provides phase change to realize the regulation and control of the mechanical properties and the hardness and hardness change of materials. Below the melting temperature, the material assumes a semi-crystalline, high modulus "hard" state; as melting proceeds, the material gradually becomes a low modulus, easily deformable "soft" state. The reversible polymer network phase change endows the ionic gel material with excellent mechanical properties, thermal response mechanical properties and shape memory capability. The mechanical properties of the material caused by the phase change of the ionic liquid are adjustable, the material is greatly influenced along with the loss of an exogenous filler or the ionic liquid, and the phase change process generates several orders of magnitude of jump change on the conductivity of the ionic conductor.
According to the preparation method of the semi-crystalline ionic gel, the hydrophilic ionic liquid monomer and the hydrophobic ionic liquid monomer react in the presence of the cross-linking agent and the initiator to construct the semi-crystalline polymer network, crystalline micro-regions in the polymer network are from long side chains (carbon chains) enough to realize the crystalline micro-regions after polymerization of the hydrophobic ionic liquid monomer, a continuous phase is mainly an amorphous region formed after polymerization of the hydrophilic ionic liquid monomer, the region can effectively load ionic liquid, and then the semi-crystalline polymer network is soaked and filled with the ionic liquid to obtain the semi-crystalline ionic gel. The side chains of the hydrophobic ionic liquid in the network are gathered to form a crystalline micro-region as a phase change unit, and the network formed by the hydrophilic ionic liquid effectively loads the ionic liquid.
The semi-crystalline ionic gel material provided by the application can be used for sensors and actuators, and has a shape memory function, so that repeated recycling of the material is realized.
Drawings
To more clearly illustrate the technical solutions of the embodiments of the present application, the drawings required in the embodiments will be briefly described below, and it should be understood that the following drawings only illustrate some embodiments of the present application and therefore should not be considered as limiting the scope of the present application.
FIG. 1 is a schematic diagram of a semicrystalline ionic gel provided herein;
FIG. 2 is a schematic diagram of a method of preparing a semicrystalline ionic gel provided herein;
FIG. 3 shows BeMA 50 -optical and polarization micrographs before and after the melting temperature of IL 35;
FIG. 4 shows BeMA 50 -visible spectrum before and after IL35 phase transition;
FIG. 5 shows BeMA 50 -a dynamic mechanical property profile of IL 35;
FIG. 6 is BeMA 50 -tensile property test plots before and after IL35 phase change;
FIG. 7 is BeMA 50 -ionic conductivity versus temperature curve of IL 35;
FIG. 8 is BeMA 50 -a schematic representation of the electrical conductivity of IL35 material with repeatability at 26 ℃ and 60 ℃;
FIG. 9 is BeMA 50 IL35 can implement a schematic representation of shape memory;
FIG. 10 is BeMA 50 -a schematic representation of an IL35 sample as driver;
FIG. 11 shows BeMA 50 -a schematic representation of the process of simulating blooming of a fresh flower for an IL35 sample;
FIG. 12 shows BeMA 50 A schematic representation of an IL35 sample used as a touch sensor;
FIG. 13 is a plot of storage modulus versus melting for the examples and comparative examples;
FIG. 14 is a DSC curve of the samples of examples and comparative examples.
Detailed Description
The terms as used herein:
"consisting of 8230%" \8230, preparation "and" comprising "are synonymous. As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
The conjunction "consisting of 823070, 8230composition" excludes any unspecified elements, steps or components. If used in a claim, the phrase is intended to claim as closed, meaning that it does not contain materials other than those described, except for the conventional impurities associated therewith. When the phrase "consisting of (8230) \8230; occurs in a clause of the subject matter of the claims rather than immediately after the subject matter, it only defines the elements described in the clause; other elements are not excluded from the claims as a whole.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or range defined by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4," "1 to 3," "1 to 2 and 4 to 5," "1 to 3 and 5," and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
In the examples, the parts and percentages are by mass unless otherwise indicated.
"part by mass" means a basic unit of measure indicating a mass ratio of a plurality of components, and 1 part may represent an arbitrary unit mass, for example, 1g or 2.689 g. If the parts by mass of the component A are a parts and the parts by mass of the component B are B parts, the mass ratio of the component A to the component B is expressed as a: b. alternatively, the mass of the A component is aK and the mass of the B component is bK (K is an arbitrary number, and represents a multiple factor). It is not to be misunderstood that the sum of the parts by mass of all the components is not limited to the limit of 100 parts, unlike the parts by mass.
"and/or" is used to indicate that one or both of the illustrated conditions may occur, e.g., a and/or B includes (a and B) and (a or B).
A semi-crystalline ionic gel is composed of a semi-crystalline polymer and an ionic liquid loaded in the semi-crystalline polymer.
The schematic diagram is shown in fig. 1.
The application also provides a preparation method of the semi-crystalline ionic gel, which comprises the following steps:
mixing raw materials including a monomer compound, a cross-linking agent and an initiator, reacting to obtain the semi-crystalline polymer, and then soaking the semi-crystalline polymer in the ionic liquid to obtain the semi-crystalline ionic gel;
the monomer compound includes a hydrophobic ionic liquid monomer and an ionophilic liquid monomer.
The flow diagram of the preparation method is shown in figure 2.
In an alternative embodiment, the hydrophobic liquid monomer comprises one or more of a C15-C25 alkyl acrylate compound, a C15-C25 vinyl compound, a C15-C25 styrene compound, a C15-C25 alkyl methacrylate compound, and a C15-C25 acrylamide compound.
In an alternative embodiment, the ionophilic liquid monomer comprises a C1-C5 alkyl acrylate compound, a C1-C5 vinyl compound, a C1-C5 styrene compound, a C1-C5 alkyl methacrylate compound, and a C15-C25 acrylamide compound.
In an alternative embodiment, one or more of the photoinitiator, thermal initiator, redox initiator;
in an alternative embodiment, the initiator comprises a photoinitiator comprising one or more of 2,4,6 (trimethylbenzoyl) diphenylphosphine oxide, 2,4, -trimethylbenzoylphosphonic acid ethyl ester, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholino-1-propanone, 2-isopropylthioxanthone, 4-dimethylamino-benzoic acid ethyl ester, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, benzoin dimethyl ether, methyl o-benzoylbenzoate, 4-chlorobenzophenone, 4-phenylbenzophenone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone;
in an alternative embodiment, the thermal initiator comprises one or more of azoisobutyronitrile, 4' -azo (4-cyanovaleric acid), azobisisobutyronitrile hydrochloride, benzoyl peroxide;
in an alternative embodiment, the redox initiator comprises one or more of hydrogen peroxide/ferrous salts, amine per disulfate/tetramethylethylenediamine, potassium per disulfate/sodium sulfite, dibenzoyl peroxide/N, N-dimethylaniline.
In an alternative embodiment, the crosslinking agent comprises one or more of a multifunctional acrylic crosslinking agent, a multifunctional styrenic crosslinking agent, a multifunctional vinyl crosslinking agent, a multifunctional acrylamide crosslinking agent;
in an alternative embodiment, the multifunctional acrylic crosslinker comprises one or more of poly (ethylene glycol) diacrylate, poly (ethylene glycol) methyl diacrylate, 1, 3-propanediol diacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediol diacrylate;
in an alternative embodiment, the multifunctional acrylamide-based cross-linking agent comprises methylene bis acrylamide;
in an alternative embodiment, the multi-functional styrenic crosslinker comprises divinylbenzene;
in an alternative embodiment, the multifunctional vinyl-based crosslinker comprises diethylene glycol divinyl ether.
In an alternative embodiment, the ionic liquid comprises one or more of quaternary ammonium salt ionic liquid, imidazole ionic liquid and quaternary phosphonium ionic liquid;
in an alternative embodiment, the quaternary ammonium salt ionic liquid comprises tributylmethylammonium bistrifluoromethanesulfonylimide salt;
in an alternative embodiment of the method according to the invention, the imidazole ionic liquid comprises 1-methyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-ethyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-propyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-butyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-methyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-methyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole hexafluorophosphate 1-butyl-3-methylimidazolium hexafluorophosphate, 1-methyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-methyl-3-methylimidazolium bromide, 1-ethyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium bromide, 1-methyl-3-methylimidazolium perchlorate, 1-ethyl-3-methylimidazolium perchlorate, 1-butyl-3-methylimidazolium perchlorate, 1-methyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-methyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, and, one or more of 1-ethyl-3-methylimidazole trifluoroacetate or 1-butyl-3-methylimidazole trifluoroacetate;
in an alternative embodiment, the quaternary phosphonium based ionic liquid comprises tetrabutylphosphonium bistrifluoromethane sulphonimide salt and/or tributylethylphosphonbistrifluoromethane sulphonimide salt.
In an alternative embodiment, the mass ratio of the monomer compound, the initiator, the crosslinking agent, and the ionic liquid is 1: (0.0001-0.05): (0.0001-0.1): (0.1-20);
in an alternative embodiment, the mass ratio of the semicrystalline polymer and the ionic liquid is 1: (0.01-10).
The mass ratio of the monomer compound, the initiator, the crosslinking agent and the ionic liquid can be 1:0.0001:0.0001:0.1, 1:0.05:0.0001:0.1, 1:0.0001:0.1:0.1, 1:0.01:0.0001:0.1, 1:0.0001:0.01:0.1, 1:0.0001:0.0001: 1. 1:0.05:0.1:20 or 1: (0.0001-0.05): (0.0001-0.1): (0.1-20); the mass ratio of the semi-crystalline polymer to the ionic liquid may be 1:0.01, 1:0.1, 1: 1. 1: 2. 1: 3. 1: 4. 1: 5. 1: 6. 1: 7. 1: 8. 1: 9. 1:10 or 1: (0.01-10).
In an alternative embodiment, the reaction comprises one or more of a photoinitiated reaction, a thermally initiated reaction, and a redox initiated reaction;
in an alternative embodiment, the photoinitiated reaction is carried out under the condition that the power density of a light source is 1mW/cm 2 -1000mW/cm 2 The wavelength is 200nm-450nm, and the time is 0.01h-24h;
optionally, the light source power density of the photoinitiated reaction may be 1mW/cm 2 、10mW/cm 2 、100mW/cm 2 、200mW/cm 2 、300mW/cm 2 、400mW/cm 2 、500mW/cm 2 、600mW/cm 2 、700mW/cm 2 、800mW/cm 2 、900mW/cm 2 、1000mW/cm 2 Or 1mW/cm 2 -1000mW/cm 2 The wavelength can be any value between 200nm, 250nm, 300nm, 350nm, 400nm, 450nm or any value between 200nm and 450nm, and the time can be any value between 0.01h, 0.1h, 1h, 2h, 4h, 6h, 8h, 10h, 12h, 14h, 16h, 18h, 20h, 22h, 24h or 0.01h and 24h;
in an alternative embodiment, the conditions of the thermally initiated reaction are 60 ℃ to 80 ℃,2h to 24h;
optionally, the temperature of the thermal initiation reaction may be any value between 60 ℃, 65 ℃,70 ℃, 75 ℃, 80 ℃ or 60 ℃ to 80 ℃, and the time may be any value between 2h, 4h, 6h, 8h, 10h, 12h, 14h, 16h, 18h, 20h, 22h, 24h or 2h to 24h;
in an alternative embodiment, the redox initiation reaction is carried out at conditions ranging from 0 ℃ to 40 ℃ for 2h to 24h.
Optionally, the temperature of the redox initiation reaction may be any value between 0 ℃, 10 ℃, 20 ℃, 30 ℃, 40 ℃ or 0 ℃ and 40 ℃, and the time may be any value between 2h, 4h, 6h, 8h, 10h, 12h, 14h, 16h, 18h, 20h, 22h, 24h or 2h and 24h.
In an optional embodiment, after the mixing and before the reacting, degassing under vacuum for 1min to 30min;
optionally, the degassing time may be any value between 1min, 5min, 10min, 15min, 20min, 25min, 30min or 1min-30min;
in an alternative embodiment, the method further comprises, after the reacting and before the soaking: degassing the reaction product for 18-24 h under the conditions of vacuum state and 40-50 ℃.
Optionally, the degassing temperature may be any value between 40 ℃, 41 ℃, 42 ℃, 43 ℃,44 ℃, 45 ℃, 46 ℃, 47 ℃, 48 ℃, 49 ℃,50 ℃ or between 40 ℃ and 50 ℃, and the time may be any value between 18h, 19h, 20h, 21h, 22h, 23h, 24h or between 18h and 24h.
Embodiments of the present application will be described in detail below with reference to specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present application and should not be construed as limiting the scope of the present application. The examples, in which specific conditions are not specified, were carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
This example provides a semicrystalline ionic gel, which is prepared as follows:
5g of BeMA (behenyl methacrylate) monomer, 5g of EA (ethyl acrylate), 60mg of photoinitiator 184, 35mg of crosslinker HDDA (1, 6-hexanediol diacrylate) were mixed homogeneously to form a precursor solution. And (3) putting the precursor solution into a vacuum box body, wherein the vacuum degree is 0.1bar, and degassing is carried out for 10s. Injecting the degassed precursor liquid into the assembled glass sheet-silica gel pad-glass sheet sandwich cavity, and placing the mold into which the precursor liquid is injected into the purpleIn the outer crosslinking box, the power density is 50mW/cm 2 And crosslinking for 30min. After the reaction, the semicrystalline polymer is taken out. And (3) placing the obtained semicrystalline polymer in a vacuum drying oven, vacuum degassing for 6h at 50 ℃, and removing odor to obtain the BeMA-co-EA semicrystalline polymer. The polymer is soaked in ionic liquid EMIMTFSI (1-ethyl-3-methylimidazole bistrifluoromethylsulfonyl imide) for 72h to obtain semicrystalline ionic gel BeMA 50 IL35, where 50 refers to the percentage of BeMA in the polymer network and 35 refers to the percentage of ionic liquid in the ionic gel after soaking in ionic liquid.
The semi-crystalline ionic gels were characterized, including optical, mechanical, electrical, shape memory tests, and the results are shown in fig. 3, fig. 4, fig. 5, fig. 6. FIG. 3 shows BeMA 50 -optical and polarization micrographs before and after the melting temperature of IL 35; FIG. 4 is a spectrum of visible light before and after a phase change; FIG. 5 is BeMA 50 -dynamic mechanical properties characterization of IL 35; FIG. 6 is a tensile property test before and after phase change; FIG. 7 is BeMA 50 The ion conductivity of IL35 as a function of temperature, as can be seen from fig. 7, increases with increasing temperature and exhibits an accelerated increase in conductivity due to a phase transition in the melting temperature range; FIG. 8 is BeMA 50 -a schematic representation of the electrical conductivity of IL35 material with repeatability at 26 ℃ and 60 ℃; FIG. 9 is BeMA 50 A schematic representation of the shape memory achievable by IL 35; FIG. 10 is BeMA 50 A schematic diagram of the IL35 sample that can be used as a driver when the ambient temperature becomes high and the LED is lit to alert it;
FIG. 11 shows BeMA 50 IL35 samples can be heated by joule heating technique to simulate the process schematic of flower bloom; FIG. 12 is BeMA 50 IL35 samples can be used as a schematic representation of a touch sensor, where (a, c, e) shows that it can be used as a touch sensor and can be recycled with varying shapes depending on the application requirements, and (b, d, f) the occurrence of touch behavior can be monitored in real time by the acquisition of electrochemical signals.
Example 2
This example provides a semicrystalline ionic gel, which is prepared as follows:
3g of the monomer BeMA (behenyl methacrylate) and 7g of EA (ethyl acrylate), 60mg of photoinitiator 184 and 35mg of crosslinker HDDA (1, 6-hexanediol diacrylate) were mixed homogeneously to form a precursor solution. And (3) putting the precursor solution into a vacuum box body, wherein the vacuum degree is 0.1bar, and degassing is carried out for 10s. Injecting the degassed precursor liquid into the assembled glass sheet-silica gel pad-glass sheet sandwich cavity, and placing the mold into an ultraviolet crosslinking box at a power density of 50mW/cm 2 And crosslinking for 30min. After the reaction is completed, the semicrystalline polymer is taken out. And (3) placing the obtained semicrystalline polymer in a vacuum drying oven, vacuum degassing for 6h at 50 ℃, and removing odor to obtain the BeMA-co-EA semicrystalline polymer. The polymer is soaked in ionic liquid EMIMTFSI for 72h to obtain semi-crystalline ionic gel BeMA 30 IL56, where 30 refers to the percentage of BeMA in the polymer network and 56 refers to the percentage of ionic liquid in the ionic gel after soaking in ionic liquid.
Example 3
This example provides a semicrystalline ionic gel, which is prepared as follows:
4g of the monomer BeMA (behenyl methacrylate) and 6g of EA (ethyl acrylate), 60mg of photoinitiator 184 and 35mg of crosslinker HDDA (1, 6-hexanediol diacrylate) were mixed homogeneously to form a precursor solution. The precursor solution is put into a vacuum box body, the vacuum degree is 0.1bar, and degassing is carried out for 10s. Injecting the degassed precursor liquid into the assembled glass sheet-silica gel pad-glass sheet sandwich cavity, and placing the mold into an ultraviolet crosslinking box with a power density of 50mW/cm 2 Crosslinking for 30min. After the reaction is completed, the semicrystalline polymer is taken out. And (3) placing the obtained semicrystalline polymer in a vacuum drying oven, vacuum degassing for 6h at 50 ℃, and removing odor to obtain the BeMA-co-EA semicrystalline polymer. The polymer is soaked in ionic liquid EMIMTFSI for 72h to obtain semi-crystalline ionic gel BeMA 40 IL44, where 40 denotes the percentage of BeMA in the polymer network and 44 denotes the percentage of ionic liquid in the ionic gel after soaking in ionic liquid.
Comparative example 1
This example provides a semicrystalline ionic gel, which is prepared as follows:
10g of the monomer EA (ethyl acrylate), 60mg of the photoinitiator 184 and 35mg of the crosslinking agent HDDA (1, 6-hexanediol diacrylate) were mixed homogeneously to form a precursor solution. And (3) putting the precursor solution into a vacuum box body, wherein the vacuum degree is 0.1bar, and degassing is carried out for 10s. Injecting the degassed precursor liquid into the assembled glass sheet-silica gel pad-glass sheet sandwich cavity, and placing the mold into an ultraviolet crosslinking box at a power density of 50mW/cm 2 And crosslinking for 30min. After the reaction is completed, the semicrystalline polymer is taken out. And (3) placing the obtained polymer in a vacuum drying oven, performing vacuum degassing for 6h at 50 ℃, and removing odor to obtain the PEA polymer. The polymer is soaked in ionic liquid EMIMTFSI for 72h to obtain semi-crystalline ionic gel BeMA 0 IL70, where 0 refers to the percentage of BeMA in the polymer network and 70 refers to the percentage of ionic liquid in the ionic gel after soaking in ionic liquid.
Comparative example 2
This example provides a semicrystalline ionic gel, which is prepared as follows:
10g of BeMA monomer (behenyl methacrylate), 60mg of photoinitiator 184 and 35mg of crosslinker HDDA (1, 6-hexanediol diacrylate) were mixed uniformly to form a precursor solution. And (3) putting the precursor solution into a vacuum box body, wherein the vacuum degree is 0.1bar, and degassing is carried out for 10s. Injecting the degassed precursor liquid into the assembled glass sheet-silica gel pad-glass sheet sandwich cavity, and placing the mold into an ultraviolet crosslinking box with a power density of 50mW/cm 2 And crosslinking for 30min. After the reaction is completed, the semicrystalline polymer is taken out. And (3) placing the obtained polymer in a vacuum drying oven, vacuum degassing for 6h at 50 ℃, and removing odor to obtain the PBeMA polymer. The polymer is soaked in ionic liquid EMIMTFSI for 72h to obtain semi-crystalline ionic gel BeMA 100 IL0, where 100 refers to the percentage of BeMA in the polymer network and 0 refers to the percentage of ionic liquid in the ionic gel after soaking in ionic liquid.
The samples of examples 1, 2, 3 and comparative examples 1 and 2 were subjected to DSC test and dynamic mechanical property analysis DMA, and the results are shown in fig. 13 and 14.
Figure 13 shows that the complex modulus of the sample decreases as the melting process progresses and increases at room temperature as the crystallinity, i.e., the BeMA charge ratio, increases. And BeMA 0 IL70 does not exhibit a step-like change in mechanical properties despite the highest ionic liquid loading rate, further demonstrating that the long carbon chain of the hydrophobic ionic liquid monomer can only achieve crystalline domains after polymerization. FIG. 14 is a DSC curve of a sample, which shows that the phase transition melting temperature increases with the increasing charge ratio of BeMA, and therefore, the method can realize the adjustment of different phase transition temperatures by the selection and matching of raw materials to adapt to more specific application scenarios. And BeMA 100 The IL0 ionic liquid loading rate is 0, and further proves that the ionic liquid can be effectively loaded after the ionophilic liquid monomer is polymerized.
The phase-change micro-area is provided by the polymer network, and the preparation of the semi-crystalline ionic gel can be realized. The ionic gel can realize adjustable optical property, electrical property and mechanical property, can realize the shape memory function, and has extremely high application value in the aspects of sensing and actuators.
Finally, it should be noted that: the above embodiments are only used for illustrating the technical solutions of the present application, and not for limiting the same; although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and these modifications or substitutions do not depart from the scope of the technical solutions of the embodiments of the present application.
Moreover, those of skill in the art will understand that although some embodiments herein include some features included in other embodiments, not others, combinations of features of different embodiments are meant to be within the scope of the application and form different embodiments. For example, in the claims above, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the application and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Claims (8)
1. A semicrystalline ionic gel, characterized by consisting of a semicrystalline polymer and an ionic liquid supported in the semicrystalline polymer; the ionic liquid comprises one or more of quaternary ammonium salt ionic liquid, imidazole ionic liquid and quaternary phosphonium ionic liquid;
the preparation method of the semi-crystalline ionic gel comprises the following steps:
mixing raw materials including a monomer compound, a cross-linking agent and an initiator, reacting to obtain the semi-crystalline polymer, and then soaking the semi-crystalline polymer in the ionic liquid to obtain the semi-crystalline ionic gel;
the monomer compound comprises a hydrophobic ionic liquid monomer and an ionophilic liquid monomer;
the hydrophobic ionic liquid monomer comprises one or more of C15-C25 alkyl acrylate compounds, C15-C25 vinyl compounds, C15-C25 styrene compounds, C15-C25 alkyl methacrylate compounds and C15-C25 acrylamide compounds;
the ionic-philic liquid monomer comprises a C1-C5 alkyl acrylate compound, a C1-C5 vinyl compound, a C1-C5 styrene compound, a C1-C5 alkyl methacrylate compound and a C15-C25 acrylamide compound.
2. The semi-crystalline ionic gel of claim 1, wherein the initiator comprises one or more of a photoinitiator, a thermal initiator, a redox initiator;
the photoinitiator comprises one or more of 2,4,6 (trimethylbenzoyl) diphenylphosphine oxide, 2,4, -trimethylbenzoylphosphonic acid ethyl ester, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholino-1-propanone, 2-isopropylthioxanthone, 4-dimethylamino-benzoic acid ethyl ester, 1-hydroxy-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, benzoin dimethyl ether, methyl o-benzoylbenzoate, 4-chlorobenzophenone, 4-phenylbenzophenone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone;
the thermal initiator comprises one or more of azoisobutyronitrile, 4' -azo (4-cyano valeric acid), azodiisobutyronitrile hydrochloride and benzoyl peroxide;
the redox initiator comprises one or more of hydrogen peroxide/ferrous salt, ammonium peroxodisulfate/tetramethyl ethylenediamine, potassium peroxodisulfate/sodium sulfite and dibenzoyl peroxide/N, N-dimethylaniline.
3. The semi-crystalline ionic gel according to claim 1, wherein the cross-linking agent comprises one or more of a multifunctional acrylic cross-linking agent, a multifunctional styrenic cross-linking agent, a multifunctional vinylic cross-linking agent, and a multifunctional acrylamide cross-linking agent;
the multifunctional acrylic crosslinking agent comprises one or more of poly (ethylene glycol) diacrylate, poly (ethylene glycol) methyl diacrylate, 1, 3-propylene glycol diacrylate, 1, 4-butylene glycol diacrylate and 1, 6-hexanediol diacrylate;
the multifunctional acrylamide-based crosslinking agent comprises methylene bisacrylamide;
the multifunctional styrenic crosslinker comprises divinylbenzene;
the polyfunctional vinyl crosslinker comprises diethylene glycol divinyl ether.
4. The semi-crystalline ionic gel according to claim 1, characterized in that said quaternary ammonium salt-based ionic liquid comprises tributylmethylammonium bistrifluoromethanesulfonimide salt;
the imidazole ionic liquid comprises 1-methyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-ethyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-propyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-butyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-methyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-methyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole hexafluorophosphate 1-butyl-3-methylimidazolium hexafluorophosphate, 1-methyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium chloride, 1-methyl-3-methylimidazolium bromide, 1-ethyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium bromide, 1-methyl-3-methylimidazolium perchlorate, 1-ethyl-3-methylimidazolium perchlorate, 1-butyl-3-methylimidazolium perchlorate, 1-methyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-methyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, and, one or more of 1-ethyl-3-methylimidazole trifluoroacetate or 1-butyl-3-methylimidazole trifluoroacetate;
the quaternary phosphonium ionic liquid comprises tetrabutyl phosphine bistrifluoromethyl sulfonyl imide salt and/or tributyl ethyl phosphine bistrifluoromethyl sulfonyl imide salt.
5. The semi-crystalline ionic gel according to claim 1, wherein the mass ratio of the monomer compound, the initiator, the crosslinking agent, and the ionic liquid is 1: (0.0001-0.05): (0.0001-0.1): (0.1-20);
the mass ratio of the semi-crystalline polymer to the ionic liquid is 1: (0.01-10).
6. The semi-crystalline ionic gel according to claim 1, wherein the reaction comprises one or more of a photoinitiated reaction, a thermally initiated reaction, and a redox initiated reaction;
the condition of the photoinitiated reaction is that the power density of a light source is 1mW/cm 2 -1000mW/cm 2 The wavelength is 200nm-450nm, and the time is 0.01h-24h;
the conditions of the thermal initiation reaction are 60-80 ℃ and 2-24 h;
the redox initiation reaction is carried out at 0-40 ℃ for 2-24 h.
7. The semi-crystalline ionic gel according to any one of claims 1 to 6, further comprising degassing under vacuum for 1min to 30min after the mixing and before the reaction;
after the reaction and before the soaking, the method further comprises the following steps: degassing the reaction product in a vacuum state at 40-50 ℃ for 18-24 h.
8. Use of a semicrystalline ionic gel as defined in any one of claims 1 to 7 in sensors, actuators.
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