CN114044852A - Polymerizable eutectic solvent, conductive elastomer and preparation method thereof - Google Patents
Polymerizable eutectic solvent, conductive elastomer and preparation method thereof Download PDFInfo
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- CN114044852A CN114044852A CN202111551197.4A CN202111551197A CN114044852A CN 114044852 A CN114044852 A CN 114044852A CN 202111551197 A CN202111551197 A CN 202111551197A CN 114044852 A CN114044852 A CN 114044852A
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- Prior art keywords
- eutectic solvent
- hydrogen bond
- choline
- polymerizable eutectic
- conductive elastomer
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- 230000005496 eutectics Effects 0.000 title claims abstract description 67
- 239000002904 solvent Substances 0.000 title claims abstract description 65
- 229920001971 elastomer Polymers 0.000 title claims abstract description 61
- 239000000806 elastomer Substances 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 33
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 29
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims abstract description 29
- 229960003237 betaine Drugs 0.000 claims abstract description 29
- 229960001231 choline Drugs 0.000 claims abstract description 24
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- 238000013007 heat curing Methods 0.000 claims abstract description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 238000001723 curing Methods 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 claims description 4
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012620 biological material Substances 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001384 succinic acid Substances 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
- RPERJPYDELTDMR-UHFFFAOYSA-K 2-hydroxyethyl(trimethyl)azanium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C[N+](C)(C)CCO.C[N+](C)(C)CCO.C[N+](C)(C)CCO.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O RPERJPYDELTDMR-UHFFFAOYSA-K 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 229960003257 choline citrate Drugs 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 238000000016 photochemical curing Methods 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- VSYDLUXFKAXBBY-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(COCCO)O Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(COCCO)O VSYDLUXFKAXBBY-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- ARKFKCBERVQXGI-DFWYDOINSA-M (2s)-2-amino-5-hydroxy-5-oxopentanoate;2-hydroxyethyl(trimethyl)azanium Chemical compound [H+].C[N+](C)(C)CCO.[O-]C(=O)[C@@H](N)CCC([O-])=O ARKFKCBERVQXGI-DFWYDOINSA-M 0.000 claims 1
- KKMWAPWLGBMQCO-KSBRXOFISA-L (z)-but-2-enedioate;2-hydroxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCO.C[N+](C)(C)CCO.[O-]C(=O)\C=C/C([O-])=O KKMWAPWLGBMQCO-KSBRXOFISA-L 0.000 claims 1
- QWJSAWXRUVVRLH-LREBCSMRSA-M 2-hydroxyethyl(trimethyl)azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound C[N+](C)(C)CCO.OC(=O)[C@H](O)[C@@H](O)C([O-])=O QWJSAWXRUVVRLH-LREBCSMRSA-M 0.000 claims 1
- VYFIOQBWPIRIMH-UHFFFAOYSA-L 2-hydroxyethyl(trimethyl)azanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.C[N+](C)(C)CCO.C[N+](C)(C)CCO VYFIOQBWPIRIMH-UHFFFAOYSA-L 0.000 claims 1
- ZKMDOYRDBAGOAD-UHFFFAOYSA-L butanedioate;2-hydroxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCO.C[N+](C)(C)CCO.[O-]C(=O)CCC([O-])=O ZKMDOYRDBAGOAD-UHFFFAOYSA-L 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- 238000001029 thermal curing Methods 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000029663 wound healing Effects 0.000 abstract 1
- 239000000370 acceptor Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 7
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000002608 ionic liquid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- FTCIOUYXOOXMBV-UHFFFAOYSA-N OC(=O)c1ccccc1C(O)=O.C=CC(=O)OCCOCCOC(=O)C=C Chemical compound OC(=O)c1ccccc1C(O)=O.C=CC(=O)OCCOCCOC(=O)C=C FTCIOUYXOOXMBV-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012806 monitoring device Methods 0.000 description 1
- -1 photoinitiator 1173 Chemical compound 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Images
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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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
- C08F222/1063—Esters of polycondensation macromers of alcohol terminated polyethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a polymerizable eutectic solvent, a conductive elastomer and a preparation method thereof. The polymerizable eutectic solvent is obtained by blending a hydrogen bond acceptor and a hydrogen bond donor at the temperature of 60-100 ℃, wherein the hydrogen bond acceptor comprises polycarboxylic choline and/or polycarboxylic betaine, the hydrogen bond donor comprises an imidazole monomer, and the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1: 1. the elastomer comprises a polymerizable eutectic solvent, a cross-linking agent and an initiator, and is prepared under the condition of light or heat curing. The conductive elastomer prepared by using the polymerizable eutectic solvent has unique ionic conductivity, good optical transparency and biocompatibility, and has wide application prospects in biosensors, wound healing, cell tissue engineering and motion monitoring.
Description
Technical Field
The invention relates to a polymerizable eutectic solvent, a conductive elastomer and a preparation method thereof, and belongs to the technical field of ionic liquid.
Background
The eutectic solvent belongs to the subclass of ionic liquid, inherits the chemical stability and high conductivity of the ionic liquid, and has the advantages of low cost, atom utilization rate of 100%, simple preparation and the like which are not possessed by the ionic liquid. At present, the research on the eutectic solvent mainly focuses on the fields of gas capture, biomass extraction and dissolution, catalysis and the like. The polymerizable eutectic solvent refers to a eutectic solvent capable of forming a conductive elastomer through polymerization after an initiator is added. Few reports are currently made on polymerizable eutectic solvents.
The elastomer material with high transparency, stretchability, conductivity and biocompatibility has wide development prospect, and particularly has great application space in the fields of biosensors, cell tissue engineering and the like. In recent years, rapid development of bioengineering has placed higher demands on transparency, flexibility, tensile properties, electrical conductivity and high biocompatibility of elastomers. The biological materials constructed by the eutectic solvent at present have the following important defects. Firstly, the composite material is prepared by adopting the eutectic solvent and natural macromolecules (chitosan, sodium alginate and the like), and the preparation steps are complicated and the cost is high. Secondly, most research has focused on developing novel ionic gels, involving less for liquid-free elastomers. The ionic gel constructed by the eutectic solvent often has the problems of liquid leakage, poor mechanical performance and the like. Thirdly, the development of the field in biological materials is limited due to the few varieties of high-biocompatibility eutectic solvents. Therefore, a new conductive elastomer with high light transmittance, high mechanical properties and conductivity is required to be searched.
Disclosure of Invention
[ problem ] to
The existing polymerizable eutectic solvent has few types and poor biocompatibility, and the existing elastomer preparation method has the problems of complicated steps, low biocompatibility, possible liquid leakage, poor mechanical property and the like.
[ solution ]
In order to overcome the defects of the prior art, the invention provides a preparation method of an imidazole polymerizable eutectic solvent. Meanwhile, the invention also aims to provide a conductive elastomer. The elastomer prepared by the invention has high light transmission, conductivity, high tensile property and high biocompatibility.
The invention firstly provides a polymerizable eutectic solvent, which comprises a hydrogen bond donor and a hydrogen bond acceptor, wherein the hydrogen bond acceptor comprises polycarboxylic choline and/or polycarboxylic betaine, the hydrogen bond donor comprises an imidazole monomer, and the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1: 1.
In one embodiment, the polycarboxylic acid choline includes one or more of glutamic acid choline, malic acid choline, fumaric acid choline, maleic acid choline, succinic acid choline, oxalic acid choline, malonic acid choline, citric acid choline, tartaric acid choline, and the like.
In one embodiment, the polycarboxylic acid betaine includes one or more of glutamic acid betaine, malic acid betaine, maleic acid betaine, fumaric acid betaine, succinic acid betaine, oxalic acid betaine, malonic acid betaine, citric acid betaine, tartaric acid betaine, and the like.
In one embodiment, the imidazole monomer includes one or more of 1-vinylimidazole, 2-methyl-1-vinylimidazole.
The invention also provides a preparation method of the polymerizable eutectic solvent, which comprises the following steps: and mixing the hydrogen bond donor and the hydrogen bond acceptor at the temperature of 60-100 ℃ for 0.5-2 h to obtain the polymerizable eutectic solvent.
The invention also provides a conductive elastomer which is prepared by mixing the polymerizable eutectic solvent, a cross-linking agent and an initiator and then performing photo-curing or thermosetting.
In one embodiment, the cross-linking agent is a multifunctional acrylate monomer including one or more of polyethylene glycol diacrylate, diethylene glycol diacrylate phthalate, pentaerythritol tetraacrylate, methylene bisacrylamide, ethylene glycol dimethacrylate, and the like.
In one embodiment, the initiator comprises a thermal initiator or a photoinitiator, including one of photoinitiator 2959, photoinitiator 1173, benzoyl peroxide, azobisisobutyronitrile, ammonium persulfate, and the like.
In one embodiment, the amount of the crosslinking agent added is 0.1 to 5% of the molar amount of the imidazole monomer, and the amount of the initiator added is 0.1 to 1% of the molar amount of the imidazole monomer.
In one embodiment, the photo-curing is carried out under ultraviolet light with the intensity of 10-15mw/cm2The illumination time is 20s-60 s.
In one embodiment, the heat curing refers to curing at 65 ℃ to 75 ℃ for 2 to 24 hours.
In one embodiment, the conductive elastomer is prepared by uniformly mixing the polymerizable eutectic solvent, a crosslinking agent and an initiator, stirring for 1-3 hours to obtain an elastomer prepolymer mixed solution, then pouring the elastomer prepolymer mixed solution into a vessel, and curing or thermally curing under ultraviolet irradiation to obtain the high-biocompatibility elastomer.
The present invention also provides an electronic device, a biosensor or a biomaterial comprising the above conductive elastomer.
The invention also provides application of the polymerizable eutectic solvent and the conductive elastomer in the fields of biology and electronics.
Has the advantages that:
according to the invention, through screening of the hydrogen bond receptor, the discovery is that when polycarboxylic choline or polycarboxylic betaine with high biocompatibility is selected as the hydrogen bond receptor and is mixed with the hydrogen bond donor such as imidazole monomer according to a certain proportion, the imidazole type eutectic solvent can be prepared, and has the properties of photopolymerization or thermal polymerization and intrinsic conductivity. Meanwhile, the eutectic solvent can be cured to form the conductive elastomer after a cross-linking agent and an initiator are added. The prepared elastomer has the advantages of high transparency, simple preparation method, high biocompatibility and the like.
Drawings
Figure 1, digital photograph of polymerizable eutectic solvent.
FIG. 2 is a UV spectrum of the conductive elastomer.
Fig. 3, change in resistance of a conductive elastomer at a fixed strain of 200% over 15 stretch release cycles in 50 seconds.
Detailed Description
The light transmittance of the prepared elastomer can be measured by an ultraviolet spectrometer, the conductivity of the prepared elastomer can be measured by a multimeter, and the performance of the elastomer on motion monitoring can be detected by an electrochemical workstation.
The present invention is further described below with reference to examples, but the embodiments of the present invention are not limited thereto.
Example 1
A polymerizable eutectic solvent is prepared by the following steps: 5.912g of hydrogen bond acceptor choline citrate and 5.647g of hydrogen bond donor 1-vinyl imidazole are stirred and reacted for 2h at 60 ℃ to obtain a clear polymerizable eutectic solvent.
The properties are as follows: it is a yellow flowable liquid at room temperature, see fig. 1.
Example 2
A polymerizable eutectic solvent is prepared by the following steps: 6.185g of hydrogen bond acceptor citric acid betaine and 5.647g of hydrogen bond donor 2-vinyl imidazole are stirred and reacted for 2h at 60 ℃ to obtain a clear polymerizable eutectic solvent.
The properties are as follows: is a yellow flowable liquid at room temperature.
Example 3
A polymerizable eutectic solvent is prepared by the following steps: 15.062g hydrogen bond acceptor glutamic acid choline and 6.488g hydrogen bond donor 2-methyl-1-vinyl imidazole are stirred and reacted for 1.5h at 70 ℃ to obtain a clear polymerizable eutectic solvent.
Example 4
A polymerizable eutectic solvent is prepared by the following steps: 7.140g of hydrogen bond acceptor malic choline and 19.464g of hydrogen bond donor 2-vinyl imidazole are stirred and reacted for 2 hours at the temperature of 80 ℃ to obtain a clear polymerizable eutectic solvent.
Example 5
A polymerizable eutectic solvent is prepared by the following steps: 13.232g of hydrogen bond acceptor choline fumarate and 28.235g of hydrogen bond donor 2-vinyl imidazole are stirred and reacted for 0.5h at 100 ℃ to obtain a clear polymerizable eutectic solvent.
Example 6
A polymerizable eutectic solvent is prepared by the following steps: 6.6123g of hydrogen bond acceptor maleic betaine and 11.294g of hydrogen bond donor 2-vinyl imidazole are stirred and reacted for 1.5 hours at the temperature of 60 ℃ to obtain a clear polymerizable eutectic solvent.
Example 8
A polymerizable eutectic solvent is prepared by the following steps: 6.667g hydrogen bond acceptor succinic acid betaine and 5.647g hydrogen bond donor 2-vinyl imidazole are stirred to react at 60 ℃ for 2h to obtain clear polymerizable eutectic solvent.
Example 9
A polymerizable eutectic solvent is prepared by the following steps: 6.247g of hydrogen bond acceptor, namely choline malonate, and 5.647g of hydrogen bond donor, namely 2-vinyl imidazole, are stirred and reacted for 2 hours at the temperature of 60 ℃ to obtain a clear polymerizable eutectic solvent.
In addition, when other polycarboxylic acid choline and/or polycarboxylic acid betaine in the disclosure are used as hydrogen bond acceptors, they can be prepared with imidazole monomers such as 1-vinylimidazole, 2-methyl-1-vinylimidazole to obtain a eutectic solvent.
Example 10
The preparation process of the conductive elastomer comprises the following steps:
s1, preparing a high-biocompatibility polymerizable eutectic solvent: 5.912g of hydrogen bond receptor choline citrate and 5.647g of hydrogen bond donor vinyl imidazole are stirred and reacted for 2 hours at the temperature of 60 ℃ to obtain a clear polymerizable eutectic solvent;
s2, preparing a conductive elastomer prepolymer solution: uniformly mixing 0.740g of methylene bisacrylamide, 0.135g of photoinitiator 2959 and the polymerizable eutectic solvent in the step S1, and stirring for 2 hours to obtain an elastomer prepolymer mixed solution;
s3, preparing the high-biocompatibility elastomer: pouring the elastomer prepolymer solution obtained in the step S2 into a vessel and keeping the light intensity at 13.3mw/cm2And (3) curing for 40s under the irradiation of ultraviolet light to obtain the high-biocompatibility conductive elastomer.
Transparency: the transparency can reach 83 percent.
Conductivity: the conductivity thereof was 5.5X 10-5S/cm。
Wherein, FIG. 2 is a UV spectrum of the prepared conductive elastomer, which illustrates that the elastomer has extremely high transparency.
Fig. 3 is a graph showing the resistance change of the conductive elastomer in 15 cycles of tensile release within 50 seconds at a fixed strain of 200%, which illustrates that the elastomer has excellent durability and can maintain good test sensitivity in multiple tests, and the conductive elastomer prepared by the invention can be used as a repetitive motion monitoring device.
Example 11
The preparation process of the conductive elastomer comprises the following steps:
s1, preparing a high-biocompatibility polymerizable eutectic solvent: 5.912g hydrogen bond acceptor citric acid betaine and 5.647g hydrogen bond donor vinyl imidazole are stirred and reacted for 2 hours at the temperature of 60 ℃ to obtain a clear polymerizable eutectic solvent;
s2, preparing a conductive elastomer prepolymer solution: uniformly mixing 1.480g of methylene bisacrylamide, 0.270g of photoinitiator 2959 and the polymerizable eutectic solvent in the step S1, and stirring for 3 hours to obtain an elastomer prepolymer mixed solution;
s3, preparing the high-biocompatibility elastomer: pouring the elastomer prepolymer solution obtained in the step S2 into a vessel and keeping the light intensity at 13.3mw/cm2And (3) curing for 40s under the irradiation of ultraviolet light to obtain the high-biocompatibility conductive elastomer.
Transparency: the transparency can reach 82%.
Conductivity: the conductivity thereof was 3.5X 10-5S/cm。
Example 12 the polymerizable eutectic solvent prepared in example 3 was uniformly mixed with 42.543g of polyethylene glycol diacrylate, 0.4936g of photoinitiator 1173, stirred for 1 hour to obtain an elastomer prepolymer mixed solution, and the elastomer prepolymer solution was poured into a vessel under a light intensity of 13.3mw/cm2And (5) curing for 60s under the irradiation of ultraviolet light to obtain the high-biocompatibility conductive elastomer.
Example 13
Uniformly mixing the polymerizable eutectic solvent prepared in the example 4, 4.322g of phthalic acid diethylene glycol diacrylate and 0.729g of benzoyl peroxide, stirring for 1h to obtain an elastomer prepolymer mixed solution, pouring the elastomer prepolymer solution into a vessel, and curing at the temperature of 70 ℃ for 3h to obtain the conductive elastomer with high biocompatibility.
Example 14
The polymerizable eutectic solvent prepared in example 6, 3.379g of pentaerythritol tetraacrylate and 0.4942g of azobisisobutyronitrile were uniformly mixed, stirred for 3 hours to obtain an elastomer prepolymer mixed solution, and the elastomer prepolymer solution was poured into a vessel and cured at 75 ℃ for 24 hours to obtain a conductive elastomer with high biocompatibility.
When the polymerizable eutectic solvent prepared in any one of examples 1 to 9 is used in the method of examples 10 to 14, the polymerizable eutectic solvent can be prepared to have high transparency (the transparency is more than 80%) and intrinsic conductivity (the conductivity is not less than 3.2 x 10)-5Scm-1) The conductive elastomer of (1).
Comparative example 1
If 8.3778g of choline chloride (common hydrogen bond acceptor) and 5.647g of 1-vinylimidazole are stirred and reacted for 2 hours at 60 ℃, a non-clear solution is obtained, and the method is characterized in that solid and liquid are separated from each other, and eutectic phenomena are avoided.
The properties are as follows: the phase separation liquid is turbid at room temperature, and eutectic solvent can not be formed.
Comparative example 2
If 7.3643g of choline acetate (choline monocarboxylate) and 5.647g of hydrogen bond donor 1-vinylimidazole are stirred and reacted for 2 hours at 60 ℃, a non-clear solution is obtained, and the method is characterized in that solid and liquid are separated, and eutectic phenomenon is avoided.
The properties are as follows: the phase separation liquid is turbid at room temperature, and eutectic solvent can not be formed.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. A polymerizable eutectic solvent, characterized in that the polymerizable eutectic solvent comprises a hydrogen bond donor and a hydrogen bond acceptor, the hydrogen bond acceptor comprises polycarboxylic choline and/or polycarboxylic betaine, the hydrogen bond donor comprises imidazole monomer, and the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is not less than 1: 1.
2. A polymerizable eutectic solvent according to claim 1, wherein said polycarboxylic choline comprises one or more of choline glutamate, choline malate, choline fumarate, choline maleate, choline succinate, choline oxalate, choline malonate, choline citrate, and choline tartrate; the polybasic carboxylic acid betaine comprises one or more of glutamic acid betaine, malic acid betaine, maleic acid betaine, fumaric acid betaine, succinic acid betaine, oxalic acid betaine, malonic acid betaine, citric acid betaine and tartaric acid betaine.
3. A polymerizable eutectic solvent according to claim 1, wherein said imidazole monomer comprises one or more of 1-vinylimidazole, 2-methyl-1-vinylimidazole.
4. A method for preparing a polymerizable eutectic solvent according to any one of claims 1 to 3, wherein the method comprises: and mixing the hydrogen bond donor and the hydrogen bond acceptor at the temperature of 60-100 ℃ for 0.5-2 h to obtain the polymerizable eutectic solvent.
5. A conductive elastomer, which is prepared by mixing the polymerizable eutectic solvent, a cross-linking agent and an initiator according to any one of claims 1 to 4 and then performing light or heat curing.
6. The conductive elastomer of claim 5, wherein the cross-linking agent is a multifunctional acrylate monomer, preferably comprising one or more of polyethylene glycol diacrylate, diethylene glycol diacrylate phthalate, pentaerythritol tetraacrylate, methylene bisacrylamide, and ethylene glycol dimethacrylate.
7. The conductive elastomer of claim 5 or 6, wherein the initiator comprises a thermal initiator or a photoinitiator, and comprises one or more of a photoinitiator 2959, a photoinitiator 1173, benzoyl peroxide, azobisisobutyronitrile and ammonium persulfate.
8. The conductive elastomer as claimed in any one of claims 5 to 7, wherein said photo-curing is carried out under UV light with a light intensity of 10-15mw/cm2The illumination time is 20s-60 s; the thermal curing refers to curing for 2-24h at 65-75 ℃.
9. An electronic device, biosensor or biomaterial comprising a conductive elastomer as claimed in any one of claims 5 to 8.
10. Use of the polymerizable eutectic solvent according to any one of claims 1 to 4 or the conductive elastomer according to any one of claims 5 to 8 in the fields of biology and electronics.
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CN113621100A (en) * | 2021-08-24 | 2021-11-09 | 华南理工大学 | Polymerizable eutectic solvent, dry-type ion conductor prepared from polymerizable eutectic solvent and preparation method of dry-type ion conductor |
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CN113621100A (en) * | 2021-08-24 | 2021-11-09 | 华南理工大学 | Polymerizable eutectic solvent, dry-type ion conductor prepared from polymerizable eutectic solvent and preparation method of dry-type ion conductor |
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