CN115353837A - Single-component polyion liquid adhesive and preparation method and application thereof - Google Patents

Single-component polyion liquid adhesive and preparation method and application thereof Download PDF

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CN115353837A
CN115353837A CN202211016226.1A CN202211016226A CN115353837A CN 115353837 A CN115353837 A CN 115353837A CN 202211016226 A CN202211016226 A CN 202211016226A CN 115353837 A CN115353837 A CN 115353837A
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methylimidazole
ethyl
ionic liquid
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bromide
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王鸿
王彬敏
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Nankai University
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J139/00—Adhesives based on homopolymers or 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; Adhesives based on derivatives of such polymers
    • C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J125/00—Adhesives based on homopolymers or 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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J139/00—Adhesives based on homopolymers or 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; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J141/00—Adhesives based on homopolymers or 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 bond to sulfur or by a heterocyclic ring containing sulfur; Adhesives based on derivatives of such polymers

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Abstract

The invention relates to the technical field of underwater adhesion, in particular to a mono-component polyion liquid adhesive and a preparation method and application thereof. The invention provides a single-component polyion liquid adhesive which comprises a hydrophobic single-component polyion liquid homopolymer and an organic medium. In the invention, the single-component polyion liquid adhesive can realize quick and super-strong adhesion on various substrates within 30s, and can keep long-term adhesion effect (56.7 mN.m) in water ‑1 ) And can be repeatedly used for many times.

Description

Single-component polyion liquid adhesive and preparation method and application thereof
Technical Field
The invention relates to the technical field of underwater adhesion, in particular to a single-component polyion liquid adhesive and a preparation method and application thereof.
Background
The underwater adhesive (wet adhesive) has great application value in the fields of functional coatings, (biological) electronic devices, medical treatment, ocean engineering and the like. Adhesives commonly used in life, such as acrylates, epoxies, and polyurethanes, perform well in dry environments but do not perform well in wet environments. This is because on the one hand water acts as a boundary layer to hinder the interaction between the adhesive and the surface; on the other hand, entry of water molecules into the adhesion interface hydrates/swells/degrades the adhesive molecules. Therefore, underwater high adhesion materials are always the research hotspot and difficulty in the field of engineering materials.
Inspired by the underwater super-strong adhesion property of adhered biological mussels and sandcastle worms in the ocean, the method of utilizing the complexation of bionic dopamine and polyelectrolyte and the like is a main method for preparing the adhesive in the underwater (humid) environment at present. However, the prepared adhesive has strong adhesion and can be applied in an underwater (humid) environment, the chemical synthesis operation is complicated, the curing time is long, the adhesive cannot be reused, and the scale application of the adhesive is greatly limited.
Due to their structural designability, controllability of microstructure, and reusability, supramolecular structural adhesives have received much attention in the field of underwater (wet) adhesion. However, the number of chemical structures currently available for the preparation of supramolecular adhesives is relatively small, and most of the supramolecular adhesives reported to date are not suitable for adhesion in humid or aqueous environments. Therefore, the development of a novel reusable underwater adhesive which is easy to produce, low in cost, high in adhesion efficiency and good in performance is still a problem to be solved urgently in current research.
Disclosure of Invention
The invention aims to provide a single-component polyion liquid adhesive and a preparation method and application thereof. The single-component polyion liquid adhesive can realize underwater rapid contact adhesion, and has high adhesion strength and high conductivity, and can be repeatedly used.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a single-component polyion liquid adhesive, which comprises a hydrophobic single-component polyion liquid homopolymer and an organic medium;
the organic medium comprises an organic solvent and/or an ionic liquid solvent;
the hydrophobic mono-component polyionic liquid homopolymer comprises:
Figure BDA0003812609290000011
Figure BDA0003812609290000021
Figure BDA0003812609290000031
wherein R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure BDA0003812609290000032
Figure BDA0003812609290000033
R is alkyl with 1-18 carbon atoms; m is an integer of 0 to 12;
x is Cl, br, I,
Figure BDA0003812609290000034
Figure BDA0003812609290000035
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
The molecular weight of the hydrophobic mono-component polyion liquid homopolymer is 5000-1000000 KDa.
Preferably, the dosage ratio of the hydrophobic single-component polyion liquid homopolymer to the organic medium is (0.1-1) g: (0.1-100) mL.
Preferably, the preparation method of the hydrophobic mono-component polyion liquid homopolymer comprises the following steps:
carrying out quaternization reaction on a halogenated compound and a compound containing vinyl to obtain an ionic liquid monomer;
carrying out free polymerization reaction on the ionic liquid monomer to obtain the hydrophobic mono-component polyion liquid homopolymer;
the halogenated compound comprises a compound containing-OH, -CN, -CONH 2 Halogen compounds of the functional group, -COOH, halogen compounds containing ether chains, X' (CH) 2 ) m CH 3 ，
Figure BDA0003812609290000041
Figure BDA0003812609290000042
The vinyl-containing compound includes
Figure BDA0003812609290000043
Figure BDA0003812609290000044
Wherein, X' is Cl, br or I;
x is Cl, br, I,
Figure BDA0003812609290000045
Figure BDA0003812609290000051
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure BDA0003812609290000052
Figure BDA0003812609290000053
R is alkyl with 1-18 carbon atoms; m is an integer of 0 to 12;
m is an integer of 0 to 12.
Preferably, the organic solvent is a polar organic solvent;
the polar organic solvent comprises one or more of methanol, ethanol, acetone, tetrahydrofuran, N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, butyl sulfone, dioxane, hydroxypropionic acid, ethylamine, ethylenediamine, glycerol, diglyme, 1,3-dioxolane, pyridine, formamide, acetonitrile, propanol, and isopropanol.
Preferably, the first and second liquid crystal materials are, the ionic liquid solvent comprises 1,3-dimethylimidazole iodide, 1-ethyl-3-methylimidazole bromide, 1,3-dimethylimidazole methyl sulfate, 1,3-dimethylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole iodide, 1-ethyl-3-methylimidazole ethyl sulfate, 1-ethyl-3-methylimidazole methyl sulfate, 1-ethyl-3-methylimidazole diethyl phosphate, 1-ethyl-3-methylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole trifluoromethanesulfonate, 1-ethyl-3-methylimidazole bistrifluoromethylsulfimide, 1-ethyl-3-methylimidazole dicyandiamide, 1-propyl-3-methylimidazole bromide, 1-propyl-3-methylimidazole iodide, 1-propyl-3-methylimidazole chloride, 1-butyl-3-methylimidazole 1-methylbutyl-butylbutylmethyl imidazole trifluoromethanesulfonate, 1-butylmethyl imidazole trifluoromethanesulfonate, 1-butylmethyl imidazole-3-butylmethanesulfonate, 1-butylmethyl imidazole tetrafluoroborate, 1-ethyl-3-methylimidazole-butyltrifluoromethanesulfonate, 1-butylbutylmethyl imidazole bunomethylimidazole, 1-hexyl-3-methylimidazole chloride, 1-hexyl-3-methylimidazole bromide, 1-hexyl-3-methylimidazole iodide, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-hexyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole chloride, 1-octyl-3-methylimidazole bromide, 1-octyl-3-methylimidazole tetrafluoroborate, 1-octyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole trifluoromethanesulfonate, 1-octyl-3-methylimidazole bistrifluoromethylsulfonimide salt, 1-decyl-3-methylimidazole bromide, 1-decyl-3-methylimidazole tetrafluoroborate, 1-decyl-3-methylimidazole hexafluorophosphate, 1-dodecyl-3-methylimidazole bromide, 1-dodecyl-3-methylimidazole tetrafluoroborate, 1-hexadecyl-3-methylimidazole chloride, 1-hexadecyl-3-methylimidazole bromide, 1-benzyl-3-methylimidazole chloride, 1-benzyl-3-methylimidazole bromide, 1-benzyl-3-methylimidazole chloride, 1-allylmethylimidazole chloride, 1-octyl 3-methylimidazole bromide, allylbenzyl 3-methylimidazole bromide, and so-methylimidazole bromide, 1-allyl-3-methylimidazole iodide, 1-allyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-allyl-3-methylimidazole hexafluorophosphate, 1-ethyl-2,3-dimethylimidazole iodide, 1-ethyl-2,3-dimethylimidazole tetrafluoroborate, 1-ethyl-2,3-dimethylimidazole hexafluorophosphate, 1-propyl-2,3-dimethylimidazole iodide, 1-butyl-2,3-dimethylimidazole chloride, 1-butyl-2,3-dimethylimidazole bromide, 1-butyl-2,3-dimethylimidazole tetrafluoroborate, 1-butyl-2,3-dimethylimidazole hexafluorophosphate, N-ethylpyridine bromide, N-ethylpyridine iodide, N-ethylpyridine tetrafluoroborate, N-ethylpyridine hexafluorophosphate, N-butylpyridine chloride, N-butylpyridine bromide, N-butylpyridine, N-octylpyridine chloride, N-octylpyridine hexafluorophosphate, N-octylpyridine bromide, and N-octylpyridine tetrafluoroborate bromide.
The invention also provides a preparation method of the mono-component polyion liquid adhesive, which comprises the following steps:
and mixing the hydrophobic single-component polyion liquid homopolymer with an organic medium to obtain the single-component polyion liquid adhesive.
The invention also provides application of the single-component polyion liquid adhesive in the technical scheme in the field of underwater adhesion.
Preferably, the application comprises the following steps: coating the single-component polyion liquid adhesive on the surface of a target substrate positioned under water to form an adhesive layer;
the adhesion layer is of a hierarchical pore structure.
The invention provides a single-component polyion liquid adhesive. In the invention, water molecules firstly enter the adhesion layer to serve as an H bond crosslinking agent to promote the micro-phase separation of the hydrophilic part and the hydrophobic part of the polyion liquid, and the water molecules are unevenly distributed in the adhesive film to form a multi-stage pore structure, so that the transportation of water molecules in the internal environment of the adhesion layer is promoted, and meanwhile, the synergistic action among non-covalent interactions (namely H bonds, cation-pi and electrostatic interactions) ensures that the adhesion layer has firm adhesion strength and excellent stretchability and flexibility at the interface contacted with a target substrate. The single-component polyion liquid adhesive can realize fast and super-strong adhesion on various substrates within 30s at the fastest speed, can keep long-term adhesion effect in water, and has the adhesion force reaching 56.7 mN.m at most -1 And can be repeatedly used for many times.
Drawings
FIG. 1 is a diagram of a monocomponent poly (3-hydroxymethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive;
FIG. 2 is a diagram of a solid object of stable adhesion formed on a silica gel plate immersed in water by writing the letter "NK" with a mono-component poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid adhesive on the silica gel plate through a tip for 40 s;
FIG. 3 is a graph of the adhesion performance of a monocomponent poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive on a mica substrate over time in water;
FIG. 4 is a graph of the adhesion performance of a monocomponent poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive on a polytetrafluoroethylene substrate over time in water;
FIG. 5 is a pictorial representation of a monocomponent poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive writing the letter "NK"50s on a water-soaked hydrophilic quartz substrate and rinsing with water at 2bar pressure for 1 min;
FIG. 6 is a pictorial representation of a 15s water rinse with 1.5bar pressure water after 1min in situ writing the letter "NK" on a hydrophobic polytetrafluoroethylene substrate soaked in water with a monocomponent poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive via a tip;
FIG. 7 is a scanning electron micrograph of an adhesion layer formed underwater by a mono-component poly (3- (2- ((carboxy (phenyl) methyl) amino) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchloric acid ionic liquid adhesive;
FIG. 8 is a pictorial representation of a single component poly (3- (2- ((carboxy (phenyl) methyl) amino) -2-oxyethyl) -1-vinylimidazole) bromide ionic liquid adhesive forming a stable bond after being directly dropped on a polystyrene substrate immersed in water for 40s, rinsed with water at a pressure of 2bar for 1 min;
FIG. 9 is a pictorial representation of a stable adhesion formed by the tip of a writing of the letter "NK" in situ on a silica gel plate soaked in a water solution of a monocomponent poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive for 30 seconds;
FIG. 10 is a graph of the adhesion performance of a single component poly (3- (2- ((carboxy (phenyl) methyl) amino) -2-oxyethyl) -1-vinylimidazole) bromide ionic liquid adhesive in water over time to a polystyrene substrate;
FIG. 11 is a pictorial representation of a monocomponent poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive (a) adhered to a silica gel plate and subjected to (b) stretching and (c) bending.
Detailed Description
The invention provides a single-component polyion liquid adhesive, which comprises a hydrophobic single-component polyion liquid homopolymer and an organic medium;
the organic medium comprises an organic solvent and/or an ionic liquid solvent;
the hydrophobic mono-component polyionic liquid homopolymer preferably comprises:
Figure BDA0003812609290000071
Figure BDA0003812609290000081
Figure BDA0003812609290000091
wherein R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure BDA0003812609290000092
Figure BDA0003812609290000093
R is alkyl with 1-18 carbon atoms; m is an integer of 0 to 12;
x is Cl, br, I,
Figure BDA0003812609290000094
Figure BDA0003812609290000095
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
The molecular weight of the hydrophobic mono-component polyion liquid homopolymer is 5000-1000000 KDa.
In the invention, the dosage ratio of the hydrophobic mono-component polyion liquid homopolymer to the organic medium is preferably (0.1-1) g, (0.1-100) mL, more preferably (0.1-0.5) g, (0.1-10) mL, and most preferably 0.3 g.
In the present invention, the preparation method of the hydrophobic mono-component polyion liquid homopolymer preferably comprises the following steps:
carrying out quaternization reaction on a halogenated compound and a compound containing vinyl to obtain an ionic liquid monomer;
carrying out free polymerization reaction on the ionic liquid monomer to obtain the hydrophobic single-component polyion liquid homopolymer;
the halogenated compound comprises-OH, -CN, -CONH 2 Halogen compounds of the functional group, -COOH, halogen compounds containing ether chains, X' (CH) 2 ) m CH 3 ，
Figure BDA0003812609290000101
Figure BDA0003812609290000102
The vinyl group-containing compound comprises
Figure BDA0003812609290000103
Figure BDA0003812609290000104
Wherein, X' is Cl, br or I;
x is Cl, br, I,
Figure BDA0003812609290000105
Figure BDA0003812609290000111
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure BDA0003812609290000112
Figure BDA0003812609290000113
R is alkyl with 1 to 18 carbon atoms; m is an integer of 0 to 12;
m is an integer of 0 to 12.
The invention carries out quaternization reaction on halogenated compounds and vinyl-containing compounds to obtain ionic liquid monomers.
In the present invention, the halogenated compoundPreferably comprising X' CH 2 CONH 2 、X'CH 2 OH、X'CH 2 CN、X'CH 2 COOH、X'(CH 2 CH 2 O) m CH 3 、
Figure BDA0003812609290000114
Figure BDA0003812609290000115
Figure BDA0003812609290000116
X' is preferably Cl, br, I;
Figure BDA0003812609290000117
preferably Cl - 、Br - 、I - 、
Figure BDA0003812609290000118
Figure BDA0003812609290000121
ClO 4 - 、BF 4 - 、PF 6 - 、CF 3 SO 3 - 、(CF 3 SO 2 ) 2 N - Or (CF) 3 CF 2 SO 2 ) 2 N - (ii) a m is an integer of 0 to 3;
the vinyl group-containing compound preferably comprises
Figure BDA0003812609290000122
Figure BDA0003812609290000123
Figure BDA0003812609290000124
Is Cl - 、Br - 、I - 、
Figure BDA0003812609290000125
Figure BDA0003812609290000126
ClO 4 - 、BF 4 - 、PF 6 - 、CF 3 SO 3 - 、(CF 3 SO 2 ) 2 N - Or (CF) 3 CF 2 SO 2 ) 2 N - 。
In the present invention, the molar ratio of the halogenated compound to the vinyl-containing compound is preferably (1 to 10): (10-1), more preferably (1-5): (5-1), most preferably (1-2): (2-1).
In the present invention, the quaternization is preferably carried out by mixing a halogenated compound, a vinyl-containing compound and an organic solvent. In the invention, the organic solvent is preferably one or more of methanol, acetone, ethanol, acetonitrile and dichloromethane; when the organic solvent is more than two of the above specific choices, the invention does not have any special limitation on the proportion of the specific substances, and the specific substances can be mixed according to any proportion.
In the present invention, the ratio of the mass of the halogenated compound to the volume of the organic solvent is preferably (1 to 10) g (1 to 500) mL, more preferably (2 to 8) g (1 to 200) mL, and most preferably (3 to 6) g (1 to 50) mL.
In the present invention, the temperature of the quaternization reaction is preferably 0 to 70 ℃, more preferably 20 to 55 ℃, and most preferably 45 ℃; the time is preferably from 0 to 72 hours, more preferably from 12 to 48 hours, most preferably 24 hours.
After the ionic liquid monomer is obtained, the invention carries out free polymerization reaction on the ionic liquid monomer to obtain the polyion liquid.
In the present invention, the free polymerization is preferably carried out by mixing the ionic liquid monomer, the initiator and the organic solvent.
In the invention, the initiator is preferably one or more of azobisisobutyronitrile, azobisisoheptonitrile, dimethyl azobisisobutyrate, dibenzoyl peroxide and tert-butyl peroxybenzoate initiator; when the initiator is more than two of the above specific choices, the present invention does not have any special limitation on the proportion of the above specific substances, and the specific substances can be mixed according to any proportion.
In the invention, the organic solvent preferably comprises one or more of toluene, ethylene glycol monomethyl ether, octane, butyl acetate, chlorobenzene, p-xylene, m-xylene, N-dimethylformamide, cyclohexanone, formamide and dimethyl sulfoxide; when the organic solvent is more than two of the above specific choices, the invention does not have any special limitation on the proportion of the specific substances, and the specific substances can be mixed according to any proportion.
In the present invention, the volume ratio of the mass of the ionic liquid monomer, the mass of the initiator and the organic solvent is preferably (1 to 5) g of (0.001 to 0.2) mL, more preferably (1 to 3) g of (0.005 to 0.15) g of (1 to 200) mL, and most preferably 1g of.
In the present invention, the mixing is preferably performed by mixing the ionic liquid monomer and the organic solvent and then adding the initiator.
In the present invention, the temperature of the free polymerization reaction is preferably 60 to 100 ℃, more preferably 65 to 95 ℃, and most preferably 75 ℃; the time is preferably from 0 to 72 hours, more preferably from 12 to 48 hours, most preferably 36 hours.
In the present invention, the organic medium comprises an organic solvent and/or an ionic liquid solvent. In the present invention, the organic solvent is preferably a polar organic solvent; the polar organic solvent preferably comprises one or more of methanol, ethanol, acetone, tetrahydrofuran, N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, butyl sulfone, dioxane, hydroxypropionic acid, ethylamine, ethylenediamine, glycerol, diglyme, 1,3-dioxolane, pyridine, formamide, acetonitrile, propanol, and isopropanol; when the polar organic solvent is more than two of the specific choices, the invention does not have any special limitation on the proportion of the specific substances, and the specific substances are mixed according to any proportion.
In the present invention, it is preferable that, the ionic liquid solvent comprises 1,3-dimethylimidazole iodide, 1-ethyl-3-methylimidazole bromide, 1,3-dimethylimidazole methyl sulfate, 1,3-dimethylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole iodide, 1-ethyl-3-methylimidazole ethyl sulfate, 1-ethyl-3-methylimidazole methyl sulfate, 1-ethyl-3-methylimidazole diethyl phosphate, 1-ethyl-3-methylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole trifluoromethanesulfonate, 1-ethyl-3-methylimidazole bistrifluoromethylsulfimide, 1-ethyl-3-methylimidazole dicyandiamide, 1-propyl-3-methylimidazole bromide, 1-propyl-3-methylimidazole iodide, 1-propyl-3-methylimidazole chloride, 1-butyl-3-methylimidazole 1-methylbutyl-butylbutylmethyl imidazole trifluoromethanesulfonate, 1-butylmethyl imidazole trifluoromethanesulfonate, 1-butylmethyl imidazole-3-butylmethanesulfonate, 1-butylmethyl imidazole tetrafluoroborate, 1-ethyl-3-methylimidazole-butyltrifluoromethanesulfonate, 1-butylbutylmethyl imidazole bunomethylimidazole, 1-hexyl-3-methylimidazole chloride, 1-hexyl-3-methylimidazole bromide, 1-hexyl-3-methylimidazole iodide, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-hexyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole chloride, 1-octyl-3-methylimidazole bromide, 1-octyl-3-methylimidazole tetrafluoroborate, 1-octyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole trifluoromethanesulfonate, 1-octyl-3-methylimidazole bistrifluoromethylsulfonimide salt, 1-decyl-3-methylimidazole bromide, 1-decyl-3-methylimidazole tetrafluoroborate, 1-decyl-3-methylimidazole hexafluorophosphate, 1-dodecyl-3-methylimidazole bromide, 1-dodecyl-3-methylimidazole tetrafluoroborate, 1-hexadecyl-3-methylimidazole chloride, 1-hexadecyl-3-methylimidazole bromide, 1-benzyl-3-methylimidazole chloride, 1-benzyl-3-methylimidazole bromide, 1-benzyl-3-methylimidazole chloride, 1-allylmethylimidazole chloride, 1-octyl 3-methylimidazole bromide, allylbenzyl 3-methylimidazole bromide, and so-methylimidazole bromide, 1-allyl-3-methylimidazole iodide, 1-allyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-allyl-3-methylimidazole hexafluorophosphate, 1-ethyl-2,3-dimethylimidazole iodide, 1-ethyl-2,3-dimethylimidazole tetrafluoroborate, 1-ethyl-2,3-dimethylimidazole hexafluorophosphate, 1-propyl-2,3-dimethylimidazole iodide, 1-butyl-2,3-dimethylimidazole chloride, 1-butyl-2,3-dimethylimidazole bromide, 1-butyl-2,3-dimethylimidazole tetrafluoroborate, 1-butyl-2,3-dimethylimidazole hexafluorophosphate, N-ethylpyridine bromide, N-ethylpyridine iodide, N-ethylpyridine tetrafluoroborate, N-ethylpyridine hexafluorophosphate, N-butylpyridine chloride, N-butylpyridine bromide, N-butylpyridine tetrafluoroborate, N-butylpyridine octylpyridine, N-octylpyridine chloride, N-octylpyridine hexafluorophosphate, and N-octylpyridine bromide; when the ionic liquid solvent is more than two of the specific choices, the proportion of the specific substances is not limited in any way, and the specific substances can be mixed according to any proportion.
The invention also provides a preparation method of the mono-component polyion liquid adhesive, which comprises the following steps:
and mixing the hydrophobic single-component polyion liquid homopolymer with an organic medium to obtain the single-component polyion liquid adhesive.
In the present invention, the mixing is preferably performed under stirring conditions, and the stirring temperature is preferably 25 to 55 ℃, more preferably 30 to 50 ℃, and most preferably 35 to 45 ℃; the time is preferably 1 to 24 hours, more preferably 1 to 20 hours, and most preferably 1 to 10 hours.
The invention also provides application of the single-component polyion liquid adhesive in the technical scheme in the field of underwater adhesion.
In the present invention, the application preferably comprises the steps of: coating the single-component polyion liquid adhesive on the surface of a target substrate positioned underwater to form an adhesive layer; the adhesion layer is of a hierarchical pore structure. In the present invention, the hierarchical pore structure is preferably uniformly distributed.
The single-component polyionic liquid adhesives provided by the present invention and methods of making and using the same are described in detail below with reference to the examples, but they should not be construed as limiting the scope of the invention.
Example 1
Preparation of poly (3-hydroxymethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesives
Figure BDA0003812609290000141
9.4g of 1-vinyl imidazole and 55g of 2-bromoethanol are dissolved in 80mL of methanol in a 250mL round-bottom flask, and the mixture reacts for 24 hours at 45 ℃ to obtain (3-hydroxymethyl-1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3-hydroxymethyl-1-vinylimidazole) bromide ionic liquid monomer into 160mL of dimethyl sulfoxide, adding 0.3g of azobisisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3-hydroxymethyl-1-vinylimidazole) bromide ionic liquid;
dissolving 20.5g of the poly (3-hydroxymethyl-1-vinylimidazole) bromide ionic liquid in 2000mL of deionized water, adding 38.7g of lithium bis (pentafluoroethanesulfonyl) imide, and stirring at room temperature for 4 hours to obtain poly (3-hydroxymethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.8g of poly (3-hydroxymethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid is dissolved in 17mL of methanol and stirred for 2 hours at room temperature to obtain the mono-component poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive (shown in a physical picture as figure 1).
Example 2
Preparation of poly (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bis (2-oxopropionic acid) boric acid ionic liquid adhesive
Figure BDA0003812609290000151
In a 250mL round bottom flask, 15g 4-methyl- (5-vinyl) thiazole, 20g 4- (bromomethyl) -1,2-benzenediol are dissolved in 50mL dichloromethane and react for 24h at 55 ℃ to obtain (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bromide ion liquid monomer;
dissolving 10g of the (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid monomer in 150mLN, N-dimethylformamide, adding 0.15g of azobisisoheptonitrile, and reacting at 75 ℃ for 48h to obtain poly (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid;
dissolving 43.3g of poly (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid in 4230mL of deionized water, adding 38g of lithium bis (2-oxopropionate) borate, and stirring at room temperature for 4h to obtain poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid;
preparation of the single-component polyion liquid adhesive:
0.5g of poly (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bis (2-oxopropanoic acid) boric acid ionic liquid was dissolved in 7mL of methanol and stirred at room temperature for 1h to obtain the one-component poly (3- (4-methyl-1,2-dihydroxy) -4-methyl- (5-vinyl) thiazole) bis (2-oxopropanoic acid) boric acid ionic liquid adhesive.
Example 3
Preparation of poly (diallyldimethylammonium) bis (2-oxo- (3-methyl) butyric acid) boric acid ionic liquid adhesive
Figure BDA0003812609290000152
Dissolving 20g of polydiallyldimethylammonium chloride ionic liquid into 2200mL of deionized water, adding 45g of lithium bis (2-oxy- (3-methyl) butyrate) borate, and stirring at room temperature for 3h to obtain poly (3,4-divinyl-1,1-dimethylpyrrole) bis (2-oxy- (3-methyl) butyrate) ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3,4-divinyl-1,1-dimethylpyrrole) bis (2-oxo- (3-methyl) butanoic acid) boronic acid ionic liquid was dissolved in 5mL of ethanol and stirred at room temperature for 1h to give the mono-component poly (3,4-divinyl-1,1-dimethylpyrrole) bis (2-oxo- (3-methyl) butanoic acid) ionic liquid adhesive.
Example 4
Preparation of poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ion liquid adhesive
Figure BDA0003812609290000161
In a 250mL round-bottom flask, 18.4g of 1- (4-vinyl) phenylimidazole and 55g of 2-bromoacetic acid are dissolved in 90mL of ethanol and react for 36h at 45 ℃ to obtain (3-carboxymethyl-1- (4-vinyl) phenylimidazole) bromide ionic liquid monomer;
dissolving 10g of the (3-carboxymethyl-1- (4-vinyl) phenylimidazole) bromide ionic liquid monomer into 190mL of dimethyl sulfoxide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) bromide ionic liquid;
dissolving 32.3g of poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) bromide ionic liquid in 3230mL of deionized water, adding 43g of sodium tetrafluoroborate, and stirring at room temperature for 3h to obtain poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid was dissolved in 6mL of 1-ethyl-3-methylimidazolium dicyanamide salt, and stirred at room temperature for 1 hour to obtain the one-component poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid adhesive.
Example 5
Preparation of poly (1- (1,2,3,4,5-pentahydroxy-6-ethyl benzene) -4-vinyl pyridine) hexafluorophosphate ionic liquid adhesive
Figure BDA0003812609290000162
In a 250mL round-bottom flask, 10g of 4-vinylpyridine, 30g of 6-ethyl-1,2,3,4,5-pentahydroxybenzene are dissolved in 50mL dichloromethane and react for 40h at 45 ℃ to obtain (1- (1,2,3,4,5-pentahydroxy-6-ethylbenzene) -4-vinylpyridine) bromide ionic liquid monomer;
dissolving 10g of the (1- (1,2,3,4,5-pentahydroxy-6-ethylbenzene) -4-vinylpyridine) bromide ionic liquid monomer in 170mL of formamide, adding 0.15g of dimethyl azodiisobutyrate, and reacting at 75 ℃ for 48h to obtain poly (1- (1,2,3,4,5-pentahydroxy-6-ethylbenzene) -4-vinylpyridine) bromide ionic liquid;
dissolving 30g of poly (1- (1,2,3,4,5-pentahydroxy-6-ethyl benzene) -4-vinyl pyridine) bromide ionic liquid in 3230mL of deionized water, adding 33g of sodium hexafluorophosphate, and stirring at room temperature for 5h to obtain poly (1- (1,2,3,4,5-pentahydroxy-6-ethyl benzene) -4-vinyl pyridine) hexafluorophosphate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (1- (1,2,3,4,5-pentahydroxy-6-ethyl benzene) -4-vinyl pyridine) hexafluorophosphate ionic liquid is dissolved in 6mL of acetone and stirred for 3 hours at room temperature to obtain the single-component poly (1- (1,2,3,4,5-pentahydroxy-6-ethyl benzene) -4-vinyl pyridine) hexafluorophosphate ionic liquid adhesive.
Example 6
Preparation of poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000171
In a 250mL round-bottom flask, 9.5g of 1-vinyl-1-H-1,2,4-triazole and 13g of 2-bromoacetamide are dissolved in 100mL of acetonitrile and react for 48H at 55 ℃ to obtain (3-acetamide-1-vinyl-1,2,4-triazole) bromide ionic liquid monomer;
dissolving 10g of (3-acetamide-1-vinyl-1,2,4-triazole) bromide ionic liquid monomer in 150mL of dimethyl sulfoxide, adding 0.2g of azodiisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3-acetamide-1-vinyl-1,2,4-triazole) bromide ionic liquid;
dissolving 10g of the poly (3-acetamide-1-vinyl-1,2,4-triazole) bromide ionic liquid in 1000mL of deionized water, adding 14g of lithium bis (trifluoromethanesulfonylimide), and stirring at room temperature for 4 hours to obtain poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid;
preparing a single-component polyion liquid adhesive:
0.4g of poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid is dissolved in 4mLN N-dimethylformamide and stirred for 2 hours at room temperature to obtain the mono-component poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid adhesive.
Example 7
Preparation of poly (N, N, N-trimethyl-1- (4-vinyl benzene) ethyl ammonium) bis (2-oxypropionic acid) boric acid ionic liquid adhesive
Figure BDA0003812609290000172
In a 250mL round-bottom flask, 20g of N, N-trimethyl-1- (4-vinyl benzene) ethylammonium and 10g of methyl bromide are dissolved in 30mL of methanol, and the mixture reacts for 36 hours at the temperature of 45 ℃ to obtain (N, N, N-trimethyl-1- (4-vinyl benzene) ethylammonium) bromide ionic liquid monomer;
dissolving 10g of the (N, N, N-trimethyl-1- (4-vinyl benzene) ethylammonium) bromide ionic liquid monomer into 190mL of dimethyl sulfoxide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (N, N, N-trimethyl-1- (4-vinyl benzene) ethylammonium) bromide ionic liquid;
dissolving 30g of poly (N, N, N-trimethyl-1- (4-vinyl benzene) ethyl ammonium) bromide ionic liquid in 3230mL of deionized water, adding 35g of lithium bis (2-oxopropionate) borate, and stirring at room temperature for 5h to obtain poly (N, N, N-trimethyl-1- (4-vinyl benzene) ethyl ammonium) bis (2-oxopropionate) borate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (N, N, N-trimethyl-1- (4-vinylphenyl) ethylammonium) bis (2-oxopropanoic acid) ionic liquid was dissolved in 9mL of acetone and stirred at room temperature for 1h to obtain the one-component poly (N, N, N-trimethyl-1- (4-vinylphenyl) ethylammonium) bis (2-oxopropanoic acid) ionic liquid adhesive.
Example 8
Preparation of poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) trifluoromethanesulfonic acid ionic liquid adhesive
Figure BDA0003812609290000181
In a 250mL round-bottom flask, 10g of 1-vinyl-1,2,4-triazole and 25g of 3-bromo-1-propylimidazole are dissolved in 50mL of ethanol and react for 24 hours at 55 ℃ to obtain (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid monomer in 160mL of butyl acetate, adding 0.15g of dibenzoyl peroxide, and reacting at 85 ℃ for 48h to obtain poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid;
dissolving 38g of poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid in 3230mL of deionized water, adding 20g of lithium trifluoromethanesulfonate, and stirring at room temperature for 3h to obtain poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) trifluoromethanesulfonate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) trifluoromethanesulfonic acid ionic liquid is dissolved in 6mLN N-dimethylformamide and stirred for 1h at room temperature to obtain the mono-component poly (3- (1-propylimidazole) -1-vinyl-1,2,4-triazole) trifluoromethanesulfonic acid ionic liquid adhesive.
Example 9
Preparation of poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000182
In a 250mL round-bottom flask, 9.5g of 1-vinyl-1,2,4-triazole and 24g of 2-bromoacetonitrile are dissolved in 90mL of dichloromethane and react for 24h at 45 ℃ to obtain (3-cyanomethyl-1-vinyl-1,2,4-triazole) bromide ionic liquid monomer;
dissolving 10g of (3-cyanomethyl-1-vinyl-1,2,4-triazole) bromide ionic liquid monomer in 170mL of dimethyl sulfoxide, adding 0.2g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bromide ionic liquid;
dissolving 21.8g of poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bromide ionic liquid in 2000mL of deionized water, adding 34.5g of lithium bis (trifluoromethanesulfonylimide), and stirring at room temperature for 6h to obtain poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid;
preparing a single-component polyion liquid adhesive:
0.3g of poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid is dissolved in 4mL of dichloromethane and stirred at room temperature for 4 hours to obtain a single-component poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonimide) ionic liquid adhesive.
Example 10
Preparation of poly (3- (1-butylimidazole) -1-vinylimidazole) tetraphenylboronic acid ionic liquid adhesive
Figure BDA0003812609290000191
Dissolving 10g of 1-vinyl imidazole and 35g of 3-bromo-1-butyl imidazole in 60mL of acetone in a 250mL round-bottom flask, and reacting at 45 ℃ for 24 hours to obtain (3- (1-butyl imidazole) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (1-butylimidazole) -1-vinylimidazole) bromide ionic liquid monomer in 190mL of chlorobenzene, adding 0.15g of tert-butyl peroxybenzoate, and reacting at 75 ℃ for 48 hours to obtain poly (3- (1-butylimidazole) -1-vinylimidazole) bromide ionic liquid;
dissolving 38g of poly (3- (1-butylimidazole) -1-vinylimidazole) bromide ionic liquid in 3230mL of deionized water, adding 20g of sodium tetraphenylborate, and stirring at room temperature for 3 hours to obtain poly (3- (1-butylimidazole) -1-vinylimidazole) tetraphenylborate ionic liquid;
preparation of the single-component polyion liquid adhesive:
0.5g of poly (3- (1-butylimidazole) -1-vinylimidazole) tetraphenylboronic acid ionic liquid was dissolved in 10mL of 1-ethyl-3-methylimidazole bromide and stirred at room temperature for 1h to obtain the one-component poly (3- (1-butylimidazole) -1-vinylimidazole) tetraphenylboronic acid ionic liquid adhesive.
Example 11
Poly (3-, (b)Preparation of (3-ethyl-1-acetamidoimidazole) bis (trifluoromethanesulfonyl) imide) -1-vinylimidazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000201
In a 250mL round-bottom flask, 10g of 1-vinyl imidazole and 30g of (3-bromoethyl-1-acetamidoimidazole) bromine are dissolved in 55mL of acetonitrile and react for 28h at 55 ℃ to obtain a 3- ((3-ethyl-1-acetamidoimidazole) bromine) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the 3- ((3-ethyl-1-acetamidoimidazole) bromine) -1-vinylimidazole) bromide ionic liquid monomer into 170mLN, N-dimethylformamide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (3- ((3-ethyl-1-acetamidoimidazole) bromine) -1-vinylimidazole) bromide ionic liquid;
dissolving 34g of poly (3- ((3-ethyl-1-acetamidoimidazole) bromine) -1-vinylimidazole) bromide ionic liquid in 3230mL of deionized water, adding 60g of lithium bis (trifluoromethanesulfonyl) imide, and stirring at room temperature for 3h to obtain poly (3- ((3-ethyl-1-acetamidoimidazole) bis (trifluoromethanesulfonyl) imide) -1-vinylimidazole) bis (trifluoromethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly 3- ((3-ethyl-1-acetamidoimidazole) bis (trifluoromethanesulfonyl) imide) -1-vinylimidazole) bis (trifluoromethanesulfonyl) imide ionic liquid is dissolved in 9mL of 1-octyl-3-methylimidazole chloride, and the mixture is stirred at room temperature for 4 hours to obtain the single-component poly 3- ((3-ethyl-1-acetamidoimidazole) bis (trifluoromethanesulfonyl) imide) -1-vinylimidazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive.
Example 12
Preparation of poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000202
In a 250mL round-bottom flask, 9.4g of 1-vinyl imidazole and 36g of 2-bromoacetonitrile are dissolved in 70mL of methanol and react for 24h at 45 ℃ to obtain (3-cyanomethyl-1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3-cyanomethyl-1-vinylimidazole) bromide ionic liquid monomer into 180mL of dimethyl sulfoxide, adding 0.2g of azobisisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3-cyanomethyl-1-vinylimidazole) bromide ionic liquid;
dissolving 21.4g of poly (3-cyanomethyl-1-vinylimidazole) bromide ionic liquid in 2100mL of deionized water, adding 42.6g of lithium bis (pentafluoroethanesulfonyl) imide, and stirring at room temperature for 4 hours to obtain poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.7g of poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid was dissolved in 10mL of 1-ethyl-3-methylimidazolium dicyanamide salt, and stirred at room temperature for 6 hours to obtain the one-component poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive.
Example 13
Preparation of poly (3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bis (pentafluoroethanesulfonyl) imide) -1-vinyl-1,2,4-triazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000211
In a 250mL round bottom flask, 10g of 1-vinyl-1,2,4-triazole and 35g of (3-bromoethyl-1- (1-hydroxyethyl) imidazole) bromine are dissolved in 60mL dichloromethane and react for 30h at 45 ℃ to obtain (3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bromine) -1-vinyl-1,2,4-triazole) bromide ion liquid monomer;
dissolving 10g of the (3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bromine) -1-vinyl-1,2,4-triazole) bromide ionic liquid monomer in 180mL of dimethyl sulfoxide, adding 0.15g of azobisisoheptonitrile, and reacting at 75 ℃ for 48h to obtain poly ((3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bromine) -1-vinyl-1,2,4-triazole) bromide ionic liquid;
dissolving 35g of poly ((3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bromine) -1-vinyl-1,2,4-triazole) bromide ionic liquid in 3230mL of deionized water, adding 50g of lithium bis (pentafluoroethanesulfonyl) imide, and stirring at room temperature for 3h to obtain poly ((3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bis (pentafluoroethanesulfonyl) imide) -1-vinyl-1,2,4-triazole) bis (pentafluoroethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly ((3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bis (pentafluoroethanesulfonyl) imide) -1-vinyl-1,2,4-triazole) bis (pentafluoroethanesulfonyl) imide ionic liquid was dissolved in 11mL of 1-iodo-1-allyl-3-methylimidazole, and stirred at room temperature for 1 hour to give the one-component poly ((3- ((3-ethyl-1- (1-hydroxyethyl) imidazole) bis (pentafluoroethanesulfonyl) imide) -1-vinyl-1,2,4-triazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive.
Example 14
Preparation of poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bis (2-oxopropionic acid) boric acid ionic liquid adhesive
Figure BDA0003812609290000212
1-vinyl-1,2,4-triazole, 35g of 1-bromopropyl-1,2,4-triazole is dissolved in 50mL of methanol in a 250mL round bottom flask, and the mixture reacts for 30h at 55 ℃ to obtain (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bromide ion liquid monomer;
dissolving 10g of the (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid monomer in 200mL of cyclohexanone, adding 0.15g of dimethyl azodiisobutyrate, and reacting at 75 ℃ for 48h to obtain poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid;
dissolving 35g of poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bromide ionic liquid in 3230mL of deionized water, adding 20g of lithium bis (2-oxopropionate) borate, and stirring at room temperature for 3h to obtain poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bis (2-oxopropionate) borate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bis (2-oxopropionic acid) boronic acid ionic liquid was dissolved in 6mL of dimethylacetamide and stirred at room temperature for 6h to give the one component poly (3- (1-propyl-1,2,4-triazole) -1-vinyl-1,2,4-triazole) bis (2-oxopropionic acid) boronic acid ionic liquid adhesive.
Example 15
Preparation of poly (3- (1-butyl-1,2,4-triazole) -1-vinylimidazole) hexafluorophosphate ionic liquid adhesive
Figure BDA0003812609290000221
In a 250mL round-bottom flask, 12g of 1-vinyl imidazole, 30g of 1-bromobutyl-1,2,4-triazole are dissolved in 50mL of ethanol and react for 36h at 40 ℃ to obtain (3- (1-butyl-1,2,4-triazole) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (1-butyl-1,2,4-triazole) -1-vinyl imidazole) bromide ionic liquid monomer in 190mLN, N-dimethylformamide, adding 0.15g of dibenzoyl peroxide, and reacting at 95 ℃ for 48h to obtain poly (3- (1-butyl-1,2,4-triazole) -1-vinyl imidazole) bromide ionic liquid;
dissolving 38g of poly (3- (1-butyl-1,2,4-triazole) -1-vinylimidazole) bromide ionic liquid in 3230mL of deionized water, adding 30g of sodium hexafluorophosphate, and stirring at room temperature for 6h to obtain poly (3- (1-butyl-1,2,4-triazole) -1-vinylimidazole) hexafluorophosphate ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (1-butyl-1,2,4-triazole) -1-vinylimidazole) hexafluorophosphate ionic liquid is dissolved in 12mL of dimethyl sulfoxide and stirred for 1h at room temperature to obtain the single-component poly (3- (1-butyl-1,2,4-triazole) -1-vinylimidazole) hexafluorophosphate ionic liquid adhesive.
Example 16
Preparation of poly (3-acetamide-1-vinylimidazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000222
9.4g of 1-vinyl imidazole and 12g of 2-bromoacetamide are dissolved in 30mL of ethanol in a 250mL round-bottom flask and react for 36h at 50 ℃ to obtain (3-acetamide-1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3-acetamide-1-vinylimidazole) bromide ionic liquid monomer into 160mL of dimethyl sulfoxide, adding 0.2g of azobisisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3-acetamide-1-vinylimidazole) bromide ionic liquid;
dissolving 10g of poly (3-acetamide-1-vinylimidazole) bromide ionic liquid in 1000mL of deionized water, adding 13g of lithium bis (trifluoromethanesulfonylimide), and stirring at room temperature for 4 hours to obtain poly (3-acetamide-1-vinylimidazole) bis (trifluoromethanesulfonimide) ionic liquid;
preparing a single-component polyion liquid adhesive:
0.3g of poly (3-acetamide-1-vinylimidazole) bistrifluoromethylsulfonyl imide ionic liquid is dissolved in 4mL of dimethyl sulfoxide and stirred for 1.5h at room temperature, so that the single-component poly (3-acetamide-1-vinylimidazole) bistrifluoromethylsulfonyl imide ionic liquid adhesive is obtained.
Example 17
Preparation of poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl-1,2,4-triazole) chloride ion liquid adhesive
Figure BDA0003812609290000231
In a 250mL round-bottom flask, 12g of 1-vinyl-1,2,4-triazole, 32g of 2- (2-chloroacetamide) -2-phenylacetic acid are dissolved in 60mL of acetone, and the mixture is reacted for 30h at 50 ℃ to obtain (3,4-divinyl-1,1-dimethylpyrrole) bromide ionic liquid monomer;
dissolving 10g of the (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl-1,2,4-triazole) chloride ion liquid monomer in 190mL of carbon disulfide, adding 0.15g of tert-butyl peroxybenzoate, and reacting at 95 ℃ for 48h to obtain poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl-1,2,4-triazole) chloride ion liquid;
preparation of the single-component polyion liquid adhesive:
0.5g of poly (3- (2- ((carboxy (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl-1,2,4-triazole) chloride ion liquid was dissolved in 13mL of formamide and stirred at room temperature for 1h to give the one-component poly (3- (2- ((carboxy (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl-1,2,4-triazole) chloride ion liquid adhesive.
Example 18
Preparation of poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchloric acid ionic liquid adhesive
Figure BDA0003812609290000241
In a 250mL round-bottom flask, 18.4g of 1- (4-vinyl) phenylimidazole and 54g of 2- (2-chloroacetamide) -2-phenylacetic acid are dissolved in 120mL of acetone and reacted at 45 ℃ for 24h to obtain (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) chloride ionic liquid monomer;
dissolving 10g of the (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) chloride ionic liquid monomer in 150mL of dimethyl sulfoxide, adding 0.1g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) chloride ionic liquid;
dissolving 41.1g of poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) chloride ionic liquid in 4100mL of deionized water, adding 14.3g of sodium perchlorate, and stirring at room temperature for 5h to obtain poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchlorate ionic liquid;
preparation of the single-component polyion liquid adhesive:
0.4g of poly (3- (2- ((carboxy (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchloric acid ionic liquid is dissolved in 6mL of methanol and stirred at room temperature for 2h to obtain the mono-component poly (3- (2- ((carboxy (phenyl) methyl) ammonia) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchloric acid ionic liquid adhesive.
Example 19
Preparation of poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000242
In a 250mL round-bottom flask, 20g of 1-vinyl imidazole and 55g of 2- (2-methoxyethoxy) bromoethane are dissolved in 120mL of acetonitrile and react at 55 ℃ for 24 hours to obtain (3- (2- (2-methoxyethoxy) ethyl) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bromide ionic liquid monomer in 190mLN N-dimethylformamide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bromide ionic liquid;
dissolving 30g of poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bromide ionic liquid in 3230mL of deionized water, adding 43g of lithium bis (pentafluoroethanesulfonyl) imide, and stirring at room temperature for 3h to obtain poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid was dissolved in 6mL of 1-ethyl-3-methylimidazolium dicyanamide salt and stirred at room temperature for 4 hours to obtain the one-component poly (3- (2- (2-methoxyethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive.
Example 20
Preparation of poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000251
In a 250mL round-bottom flask, 20g of 4-methyl- (5-vinyl) thiazole and 35g of 2- (2-ethoxyethoxy) ethyl bromide are dissolved in 80mL of dichloromethane and react at 50 ℃ for 24 hours to obtain (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid monomer in 160mL of formamide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid;
dissolving 26g of poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bromide ionic liquid in 3230mL of deionized water, adding 33g of lithium bis (trifluoromethanesulfonyl) imide, and stirring at room temperature for 3h to obtain poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bis (trifluoromethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bis (trifluoromethanesulfonyl) imide ionic liquid was dissolved in 7mL of glycerol and stirred at room temperature for 2 hours to obtain the one-component poly (3- (2- (2-ethoxyethoxy) ethyl) -4-methyl- (5-vinyl) thiazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive.
Example 21
Preparation of poly (1- (2-ethoxyethyl) -4-vinylpyridine) bis (2-oxy- (3-phenyl) butyric acid) boric acid ionic liquid adhesive
Figure BDA0003812609290000252
In a 250mL round-bottom flask, 19g 4-vinyl pyridine and 38g 2-ethoxy ethyl bromide are dissolved in 60mL acetonitrile and react for 28h at 40 ℃ to obtain (1- (2-ethoxy ethyl) -4-vinyl pyridine) bromide ionic liquid monomer;
dissolving 10g of the (1- (2-ethoxyethyl) -4-vinylpyridine) bromide ionic liquid monomer in 190mL of dimethyl sulfoxide, adding 0.15g of azobisisobutyronitrile, and reacting at 75 ℃ for 48h to obtain poly (1- (2-ethoxyethyl) -4-vinylpyridine) bromide ionic liquid;
dissolving 40g of poly (1- (2-ethoxyethyl) -4-vinylpyridine) bromide ionic liquid in 4000mL of deionized water, adding 35g of lithium bis (2-oxy- (3-phenyl) butyrate) borate, and stirring at room temperature for 3h to obtain poly (1- (2-ethoxyethyl) -4-vinylpyridine) bis (2-oxy- (3-phenyl) butyrate) ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (1- (2-ethoxyethyl) -4-vinylpyridine) bis (2-oxy- (3-phenyl) butyric acid) boric acid ionic liquid is dissolved in 8mL of ethanol and stirred for 1h at room temperature to obtain the single-component poly (1- (2-ethoxyethyl) -4-vinylpyridine) bis (2-oxy- (3-phenyl) butyric acid) boric acid ionic liquid adhesive.
Example 22
Preparation of poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl imidazole) bromide ion liquid adhesive
Figure BDA0003812609290000261
In a 250mL round-bottom flask, 9.4g 1-vinyl imidazole and 27g 2- (2-bromoacetamide) -2-phenyl acetic acid are dissolved in 60mL acetonitrile and reacted at 45 ℃ for 24h to obtain (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the 3- (2- ((carboxyl (phenyl) methyl) amino) -2-oxyethyl) -1-vinyl imidazole) bromide ionic liquid monomer in 120mL of dimethyl sulfoxide, adding 0.1g of azobisisobutyronitrile, and reacting at 75 ℃ for 48 hours to obtain poly (3- (2- ((carboxyl (phenyl) methyl) amino) -2-oxyethyl) -1-vinyl imidazole) bromide ionic liquid;
preparation of the single-component polyion liquid adhesive:
0.3g of poly 3- (2- ((carboxyl (phenyl) methyl) amino) -2-oxyethyl) -1-vinylimidazole) bromide ionic liquid is dissolved in 4mL of dimethyl sulfoxide and stirred for 2h at room temperature to obtain the single-component poly 3- (2- ((carboxyl (phenyl) methyl) amino) -2-oxyethyl) -1-vinylimidazole) bromide ionic liquid adhesive.
Example 23
Preparation of poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive
Figure BDA0003812609290000262
In a 250mL round-bottom flask, 17g of 1-vinyl imidazole and 43g of 2- (2- (2-methoxyethoxy) ethoxy) ethyl bromide are dissolved in 70mL of methanol and react at 45 ℃ for 30 hours to obtain (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinyl imidazole) bromide ionic liquid monomer;
dissolving 10g of the (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinyl imidazole) bromide ionic liquid monomer in 210mLN, N-dimethylformamide, adding 0.15g of azobisisoheptonitrile, and reacting at 85 ℃ for 48h to obtain poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinyl imidazole) bromide ionic liquid;
dissolving 25g of poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinylimidazole) bromide ionic liquid in 3000mL of deionized water, adding 33g of lithium bis (pentafluoroethanesulfonyl) imide, and stirring at room temperature for 3h to obtain poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid;
preparing a single-component polyion liquid adhesive:
0.5g of poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid was dissolved in 6mLN, N-dimethylformamide and stirred at room temperature for 4 hours to obtain the one-component poly (3- (2- (2- (2-methoxyethoxy) ethoxy) ethyl) -1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive.
Application example 1
As shown in FIG. 2, the one-component poly (3-carboxymethyl-1- (4-vinyl) phenylimidazole) tetrafluoroborate ionic liquid adhesive described in example 4 was used as an underwater adhesive to write the letter "NK" directly on a silica gel substrate soaked in water by a pipette tip without any pressing or pre-curing operation, and the adhesive was rapidly adhered to the silica gel substrate in situ by contact in 40 s.
Application example 2
As shown in FIG. 3, the one-component poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive described in example 6 was used as an underwater adhesive directly on a mica substrate painted in water without any pressing or pre-curing operation, the quick in-situ contact adhesion of the adhesive on a quartz substrate can be realized, and experimental tests show that the adhesion of the single-component poly (3-acetamide-1-vinyl-1,2,4-triazole) trifluoromethanesulfonimide ionic liquid adhesive to the mica substrate is 56.7 mN.m -1 。
Application example 3
As shown in FIG. 4, the mono-component poly (3-cyanomethyl-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive described in example 9 is used as an underwater adhesive to realize rapid in-situ contact adhesion of the adhesive on a polytetrafluoroethylene substrate directly on the polytetrafluoroethylene substrate brushed in water without any pressing or pre-curing operation, and experimental tests show that the mono-component poly (3-acetamide-1-vinyl-1,2,4-triazole) trifluoromethanesulfonimide ionic liquid adhesive has 21mN · m · adhesion to the mica substrate when the in-situ contact time is 45min -1 。
Application example 4
As shown in FIG. 5, the mono-component poly (3-cyanomethyl-1-vinylimidazole) bis (pentafluoroethanesulfonyl) imide ionic liquid adhesive prepared in example 12 is used as an underwater adhesive, and the letter "NK" is written on a quartz substrate soaked in water directly through a suction head, so that the rapid in-situ contact adhesion of the adhesive on the quartz substrate can be realized without any pressing or pre-curing operation, and an adhesion layer can still be kept intact without any peeling sign even if the adhesive layer is washed with water at the pressure of 2bar for 1 min.
Application example 5
As shown in FIG. 6, the mono-component poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive described in example 6 was used as an underwater adhesive, and the letter "NK" written on the quartz substrate was obtained by soaking the tip in water directly, and the rapid in-situ contact adhesion of the adhesive on the polytetrafluoroethylene substrate was achieved without any pressing or pre-curing operation, even though the 15s adhesive layer was washed with water at a pressure of 1.5bar and remained intact without any sign of peeling.
Application example 6
As shown in fig. 7, the mono-component poly (3- (2- ((carboxy (phenyl) methyl) amino) -2-oxyethyl) -1- (4-vinyl) phenylimidazole) perchloric acid ionic liquid adhesive described in example 18 was applied as an underwater adhesive by direct dripping onto a polystyrene substrate soaked in water, and without any application of pressure or pre-curing operation, a rapid in situ contact adhesion (< 30 s) of the adhesive on the polystyrene substrate was achieved, even with a 1min water rinse at a pressure of 2bar, the adhesive layer remained intact with no evidence of peeling.
Application example 7
As shown in fig. 8, the one-component poly (3- (2- ((carboxy (phenyl) methyl) amino) -2-oxyethyl) -1-vinylimidazole) bromide ion liquid adhesive described in example 22 was applied as an underwater adhesive directly to a polystyrene substrate soaked in water without any pressing or pre-curing operation to achieve rapid contact adhesion of the adhesive to the substrate. Experimental tests show that the adhesion of the single-component poly (3- (2- ((carboxyl (phenyl) methyl) ammonia) -2-oxyethyl) -1-vinyl imidazole) bromide ionic liquid adhesive to a polystyrene substrate is 17 mN.m. -1 (as shown in fig. 10).
Application example 8
As shown in fig. 9, the mono-component poly (3-acetamide-1-vinyl-1,2,4-triazole) bis (trifluoromethanesulfonyl) imide ionic liquid adhesive described in example 6 was used as an underwater adhesive to achieve rapid in situ contact adhesion (< 30 s) of the adhesive on a silicone substrate without any pressing or pre-curing operation by writing the letter "NK" directly on a silicone substrate immersed in water via a suction head, the adhesive layer was flexible, allowing repeated stretching and bending back and forth (as shown in fig. 11).
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.

Claims (8)

1. A one-component polyionic liquid adhesive comprising a hydrophobic one-component polyionic liquid homopolymer and an organic medium;
the organic medium comprises an organic solvent and/or an ionic liquid solvent;
the hydrophobic mono-component polyionic liquid homopolymer comprises:
Figure FDA0003812609280000011
Figure FDA0003812609280000021
wherein R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure FDA0003812609280000022
Figure FDA0003812609280000023
R is alkyl with 1-18 carbon atoms; m is an integer of 0 to 12;
x is Cl, br, I,
Figure FDA0003812609280000024
Figure FDA0003812609280000031
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
The molecular weight of the hydrophobic mono-component polyion liquid homopolymer is 5000-1000000 KDa.
2. The one-component polyionic liquid adhesive of claim 1, wherein said hydrophobic one-component polyionic liquid homopolymer and said organic medium are present in a ratio of (0.1 to 1) g: (0.1-100) mL.
3. The one-part polyionic liquid adhesive of claim 1 or 2, wherein said hydrophobic one-part polyionic liquid homopolymer is prepared by a process comprising the steps of:
carrying out quaternization reaction on a halogenated compound and a vinyl-containing compound to obtain an ionic liquid monomer;
carrying out free polymerization reaction on the ionic liquid monomer to obtain the hydrophobic single-component polyion liquid homopolymer;
the halogenated compound comprises a compound containing-OH, -CN, -CONH 2 Halogen compounds of the functional group, -COOH, halogen compounds containing ether chains, X' (CH) 2 ) m CH 3 ，
Figure FDA0003812609280000032
Figure FDA0003812609280000033
The vinyl group-containing compound comprises
Figure FDA0003812609280000034
Figure FDA0003812609280000041
Wherein, X' is Cl, br or I;
x is Cl, br, I,
Figure FDA0003812609280000042
Figure FDA0003812609280000043
ClO 4 、BF 4 、PF 6 、CF 3 SO 3 、(CF 3 SO 2 ) 2 N or (CF) 3 CF 2 SO 2 ) 2 N；
R' is R, RCN, ROH, RCONH 2 、RCOOH、
Figure FDA0003812609280000044
Figure FDA0003812609280000045
R is alkyl with 1 to 18 carbon atoms; m is an integer of 0 to 12;
m is an integer of 0 to 12.
4. The one-component polyionic liquid adhesive of claim 3, wherein said organic solvent is a polar organic solvent;
the polar organic solvent comprises one or more of methanol, ethanol, acetone, tetrahydrofuran, N-dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphoramide, butyl sulfone, dioxane, hydroxypropionic acid, ethylamine, ethylenediamine, glycerol, diglyme, 1,3-dioxolane, pyridine, formamide, acetonitrile, propanol, and isopropanol.
5. The one-part polyionic liquid adhesive of claim 3, wherein the ionic liquid solvent comprises 1,3-dimethylimidazole iodide, 1-ethyl-3-methylimidazole bromide, 1,3-dimethylimidazole methyl sulfate, 1,3-dimethylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole iodide, 1-ethyl-3-methylimidazole ethyl sulfate, 1-ethyl-3-methylimidazole methyl sulfate, 1-ethyl-3-methylimidazole diethyl phosphate, 1-ethyl-3-methylimidazole dimethyl phosphate, 1-ethyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole hexafluorophosphate, 1-ethyl-3-methylimidazole trifluoromethanesulfonate, 1-ethyl-3-methylimidazole bistrifluoromethylsulfonimide, 1-ethyl-3-methylimidazole acetate, 1-ethyl-3-methylimidazole dicyandiamide bromide, 1-propyl-3-methylimidazole, 1-propyl-3-methylbutyl-methylimidazole, 1-methylbutyl-3-methylbutyl-methylimidazole, 1-butylbutylbutylbutylmethylimidazole-butylmethanesulfonate, 1-ethyl-3-methylimidazole-fluorobutylimidazolium chloride, 1-ethyl-3-methylimidazole-methylbutyl-methylimidazole-methyl imidazole bromide, 1-3-isobutylimide iodide, 1-3-methylbutyl-methylimidazole, 1-butylimidazolium bromide, and 1-3-butylimidazolium bromide, 1-butyl-3-methylimidazolium dicyanamide salt, 1-hexyl-3-methylimidazole chloride, 1-hexyl-3-methylimidazole bromide, 1-hexyl-3-methylimidazole iodide, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-hexyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole chloride, 1-octyl-3-methylimidazole bromide, 1-octyl-3-methylimidazole tetrafluoroborate, 1-octyl-3-methylimidazole hexafluorophosphate, 1-octyl-3-methylimidazole trifluoromethanesulfonate, 1-octyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-decyl-3-methylimidazole bromide, 1-decyl-3-methylimidazole tetrafluoroborate, 1-decyl-3-methylimidazole hexafluorophosphate, 1-dodecyl-3-methylimidazole bromide, 1-dodecyl-3-methylimidazole tetrafluoroborate, 1-hexadecyl-3-methylimidazole chloride, 1-hexadecyl-3-methylimidazole bromide, 1-benzyl-3-methylimidazole chloride, 1-methylbenzyl-3-methylimidazole chloride, 1-allylbenzyl 3-methylimidazole chloride, 1-methylimidazole chloride, and benzyl 3-methylimidazole hexafluorophosphate, brominated 1-allyl-3-methylimidazole, iodinated 1-allyl-3-methylimidazole, 1-allyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-allyl-3-methylimidazole hexafluorophosphate, iodinated 1-ethyl-2,3-dimethylimidazole, 1-ethyl-2,3-dimethylimidazole tetrafluoroborate, 1-ethyl-2,3-dimethylimidazole hexafluorophosphate, iodinated 1-propyl-2,3-dimethylimidazole, chlorinated 1-butyl-2,3-dimethylimidazole, brominated 1-butyl-2,3-dimethylimidazole, brominated 1-butyl-2,3-dimethylimidazole tetrafluoroborate, 1-butyl-2,3-dimethylimidazole hexafluorophosphate, brominated N-ethylpyridine, iodinated N-ethylpyridine, N-ethylpyridine tetrafluoroborate, N-ethylpyridine hexafluorophosphate, brominated N-butylpyridine, N-octylpyridine borate, N-octylpyridine hexafluorophosphate, N-octylpyridine.
6. A process for preparing a one-part polyion liquid adhesive according to any one of claims 1 to 5, comprising the steps of:
mixing hydrophobic single-component polyion liquid homopolymer and an organic medium to obtain the single-component polyion liquid adhesive.
7. Use of the one-part polyionic liquid adhesive of any one of claims 1 to 5 in the field of underwater adhesion.
8. Use according to claim 7, characterized in that it comprises the following steps:
coating the single-component polyion liquid adhesive on the surface of a target substrate positioned under water to form an adhesive layer;
the adhesion layer is of a hierarchical pore structure.
CN202211016226.1A 2022-08-24 2022-08-24 Single-component polyion liquid adhesive and preparation method and application thereof Pending CN115353837A (en)

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CN116162200A (en) * 2023-03-07 2023-05-26 江西师范大学 Polymer electrolyte with stable lithium ion deposition function and preparation method and application thereof

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CN112500818A (en) * 2020-11-30 2021-03-16 香港中文大学（深圳） Adhesive, preparation method thereof and adhesive tape

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CN110699020A (en) * 2019-11-20 2020-01-17 湖南大学 Polyion liquid adhesive and preparation method thereof
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CN115838495A (en) * 2022-11-29 2023-03-24 南开大学 Self-supporting covalent cross-linking functional polyelectrolyte porous membrane and preparation method and application thereof
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Application publication date: 20221118