conductive pressure sensitive adhesive

Abstract

The present invention relates to an electrically conductive pressure-sensitive adhesive comprising a copolymer obtained from a reaction mixture containing an acrylic monomer mixture and a special styrene derivative, a method for producing the electrically conductive pressure-sensitive adhesive composition, and its use. The present invention also relates to the acrylic monomer itself, a method for producing it, and its use in polymerization processes.

Description

[Technical Field]

[0001] The present invention relates to an electrically conductive pressure-sensitive adhesive comprising a copolymer obtained from a reaction mixture containing an acrylic monomer mixture and a special styrene derivative, a method for producing said electrically conductive pressure-sensitive adhesive composition, and its use. [Background technology]

[0002] Conductive adhesives are primarily used in electronic devices, particularly in aerospace and automotive technologies. In recent years, conductive adhesives have also become popular as electrodes for medical and diagnostic applications such as electrocardiography (ECG), electroencephalography (EEG), and electromyography (EMG).

[0003] In this regard, US2018 / 086948 provides an adhesive composition comprising a resin and an electrically conductive material, wherein the electrically conductive material is represented by the following general formula (1) (R 1 -XZ-SO3 - ) n M n+ [In the formula, R 1 represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 40 carbon atoms and optionally substituted with or interrupted by a heteroatom; X represents a single bond, an ether group, an ester group, or an amide group; Z represents a linear or branched alkylene group having 2 to 4 carbon atoms, containing 1 to 6 fluorine atoms, and optionally containing a carbonyl group; M n+ represents a cation having one or two ammonium cation structures; and "n" represents M n+ If there is one ammonium cation structure in M, the value is 1. n+ If there are two ammonium cation structures in the compound, the number is 2.

[0004] WO2020 / 178218 discloses an ion-conductive pressure-sensitive adhesive composition comprising: a) a (meth)acrylate resin containing at least 10% by weight of a (meth)acrylate monomer containing an OH group, based on the total weight of the (meth)acrylate resin; and b) an ionic liquid. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] US Patent Application Publication No. 2018 / 086948 [Patent Document 2] International Publication No. 2020 / 178218 Summary of the Invention [Problem to be solved by the invention]

[0006] Despite the efforts already made, there is still a need for conductive pressure-sensitive adhesives that can be used to detect biosignals such as heart rate and brain waves, especially in long-term monitoring. Another aspect is the issue of sustainability, as the materials can usually only be used once. [Means for solving the problem]

[0007] In order to meet the above-mentioned needs, the present invention provides an electrically conductive pressure sensitive adhesive based on materials obtained from renewable resources. In this regard, a first aspect of the present invention is a conductive pressure sensitive adhesive comprising: a) an acrylic mixture of monomers; and b) a compound of formula (I): [ka] [In the formula, R 1 is a sulfate group (OSO3 - ), sulfonate group (SO3 - ) or a hydrogen atom (H); R 2 is a sulfate group, a sulfonate group, an alkoxy group, or a hydrogen atom, and X + is R 1 or R 2is the sulfate counterion (OSO3 - ) is a counterion that satisfies the condition that The conductive pressure-sensitive adhesive composition comprises a copolymer obtained from a reaction mixture containing the compound of formula (I).

[0008] During the course of this invention, it was discovered that the conductive pressure-sensitive adhesive compositions of the invention exhibit improved ionic conductivity and increased peel strength even in the absence of commonly used ionic liquids. The compositions of the invention also have the advantage that the compound of formula (I) can be incorporated into the acrylate polymer backbone.

[0009] The conductive pressure-sensitive adhesive composition of the present invention can be advantageously used as a dry coating and serves as a functional contact between the electrode and the skin, thereby providing a solution for long-term monitoring of biological signals. Unlike currently commercially available gel-type electrodes, it does not have the drawbacks of drying out or causing skin irritation. Furthermore, the impedance of the conductive pressure-sensitive adhesive composition of the present invention is very low even without the addition of water. [Brief explanation of the drawings]

[0010] [Figure 1] Figure 1: Impedance measurement results of the conductive pressure-sensitive adhesive (PSA) film prepared in Example 2 [Figure 2] Figure 2a: Peel test results for conductive pressure-sensitive adhesive (PSA) applied to stainless steel [Figure 3] Figure 2b: Peel test results of conductive pressure-sensitive adhesive (PSA) applied to glass [Figure 4] Figure 3a: 180° peel test results of polymer-ionic liquid blends on stainless steel with 0 wt% of compound of formula (I). [Figure 5] Figure 3b: 180° peel test results of polymer-ionic liquid blends on stainless steel with 10 wt% of the compound of formula (I). DETAILED DESCRIPTION OF THE INVENTION

[0011] Counterion X + is preferably: ·NR 3 R 4 R 5 R 6+ and R 3 ,R 4 ,R 5 and R 6 are each independently selected from C1-C8 alkyl; optionally substituted imidazolium, Colin, optionally substituted pyridinium, optionally substituted pyrrolidinium, phosphonium, Sulfonium · and mixtures thereof is selected from the group:

[0012] Counterion X + may not be a mixture of cations, but may preferably be a single species selected from one of those defined above.

[0013] X + is the NR defined above. 3 R 4 R 5 R 6+ If R 3 ,R 4 ,R 5 and R 6 are each independently selected from C2-C6 alkyl. 3 ,R 4 ,R 5 and R 6 are all the same alkyl moiety. Preferably, X + is N(C4H9)4 + is.

[0014] X + is an optionally substituted imidazolium, X + The options for X include unsubstituted imidazolium or dialkylimidazolium. Preferably, X +is 1,3-dialkylimidazolium, where each alkyl group is independently selected from linear or branched C1-C6 alkyl, more preferably linear or branched C1-C3 alkyl. Preferably, each alkyl group is independently selected from linear C1-C6 alkyl, more preferably linear C1-C3 alkyl. A particularly preferred group is 1-ethyl-3-methylimidazolium. X + may be tris(2-hydroxyethyl)methylammonium or 1-allyl-3-methylimidazolium.

[0015] X + When is an optionally substituted pyridinium, X + Options for include unsubstituted pyridinium or single N-substituted pyridinium, such as 1-alkylpyridinium, where the alkyl group is selected from linear or branched C1-C6 alkyl, preferably linear or branched C1-C4 alkyl, more preferably linear C1-C4 alkyl. X + Also included are disubstituted pyridiniums having substituents at the 1,2 or 1,3, or 1,4 positions of the pyridine ring, such as 1,2-alkylpyridinium, 1,3-alkylpyridinium, or 1,4-alkylpyridinium, where each alkyl group is independently selected from linear or branched C1-C6 alkyl, preferably linear or branched C1-C4 alkyl, more preferably linear C1-C4 alkyl.

[0016] X + When is an optionally substituted pyrrolidinium, X + Options for include unsubstituted pyrrolidinium or single N-substituted pyrrolidinium, such as 1-alkylpyrrolidinium, where the alkyl group is selected from linear or branched C1-C6 alkyl, preferably linear or branched C1-C4 alkyl, more preferably linear C1-C4 alkyl. X + Also included are disubstituted pyrrolidiniums. For example, the nitrogen ring member may be disubstituted. For example, X +is 1,1-dialkylpyrrolidinium, where each alkyl group is independently selected from straight or branched C1-C6 alkyl, preferably straight or branched C1-C4 alkyl, more preferably straight chain C1-C4 alkyl.

[0017] With respect to the R1 and R2 groups, R1 is preferably a sulfate group and R2 is an alkoxy group or a hydrogen atom.

[0018] The alkoxy groups of the compounds of formula (I), when present, are preferably selected from the group OMe, OEt, OPr and OBu, with OMe being preferred.

[0019] In a particularly preferred embodiment, the compound of formula (I) is: [ka] where X + is as defined above. Preferably, X + is N(C4H9)4 + is.

[0020] The conductive pressure-sensitive adhesive comprises a copolymer obtained from a reaction mixture comprising an acrylic mixture of monomers. In a preferred embodiment, the acrylic mixture of monomers comprises at least one of the following: methyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, acrylic acid, (C1-C18) alkyl (meth)acrylate, (meth)acrylamide, vinyl acetate, N-vinyl caprolactam, acrylonitrile, vinyl ether, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, glycidyl (meth)acrylate, and mixtures thereof, and is preferably formed from a monomer selected from the group consisting of hydroxyethyl acrylate, methyl methacrylate, n-butyl acrylate, 2-ethylhexyl acrylate, and mixtures thereof.

[0021] Particularly preferred is the embodiment of the invention in which the acrylic mixture of monomers comprises at least one, preferably all, of the following: 2-ethylhexyl acrylate (abbreviated as 2-EHA), methyl methacrylate (abbreviated as MMA), 2-hydroxyethyl acrylate (abbreviated as 2-HEA), n-butyl acrylate (abbreviated as BA).

[0022] In a preferred embodiment of the electrically conductive pressure-sensitive adhesive composition according to the present invention, the reaction mixture contains 2-EHA in an amount of 1 to 20% by weight, preferably 2 to 7% by weight, based on the total weight of the reaction mixture.

[0023] In a preferred embodiment of the electrically conductive pressure-sensitive adhesive composition according to the present invention, the reaction mixture contains 1 to 7% by weight, preferably 2 to 5% by weight, of MMA, based on the total weight of the reaction mixture.

[0024] In a preferred embodiment of the electrically conductive pressure-sensitive adhesive composition according to the present invention, the reaction mixture contains 2-HEA in an amount of 15 to 40% by weight, preferably 20 to 35% by weight, based on the total weight of the reaction mixture.

[0025] In a preferred embodiment of the electrically conductive pressure-sensitive adhesive composition according to the present invention, the reaction mixture contains BA in an amount of 40 to 80% by weight, preferably 55 to 65% by weight, based on the total weight of the reaction mixture.

[0026] In a preferred embodiment of the electrically conductive pressure-sensitive adhesive composition according to the invention, the compound of formula (I) is present in the reaction mixture in an amount of 0.1 to 50% by weight, preferably 0.2 to 30% by weight, in particular 0.5 to 10% by weight, based on the total weight of the reaction mixture.

[0027] During the course of the present invention, it was surprisingly found that the addition of an ionic liquid to a conductive pressure-sensitive adhesive composition results in a faster increase in peel strength over time compared to compositions containing either the ionic liquid alone or the compound of formula (I). Thus, in a preferred embodiment, the conductive pressure-sensitive adhesive composition further comprises an ionic liquid.

[0028] The ionic liquid optionally included in the conductive pressure-sensitive adhesive composition is preferably a non-toxic, non-irritating ionic liquid that provides ionic conductivity.

[0029] More specifically, the ionic liquid may be imidazolium acetate, imidazolium sulfonate, imidazolium chloride, imidazolium sulfate, imidazolium phosphate, imidazolium thiocyanate, imidazolium dicyanamide, imidazolium benzoate, imidazolium triflate, choline triflate, choline saccharinate, choline sulfamate, pyridinium acetate, pyridinium sulfonate, pyridinium chloride, pyridinium sulfate, pyridinium phosphate, pyridinium thiocyanate, pyridinium dicyanamide, pyridinium benzoate, pyridinium triflate, pyrrolidinium acetate, pyrrolidinium sulfonate, pyrrolidinium chloride, pyrrolidinium sulfate, pyrrolidinium phosphate, pyrrolidinium thiocyanate, pyrrolidinium dicyanamide, pyrrolidinium The benzoate, pyrrolidinium triflate, phosphonium acetate, phosphonium sulfonate, phosphonium chloride, phosphonium sulfate, phosphonium phosphate, phosphonium thiocyanate, phosphonium dicyandiamide, phosphonium benzoate, phosphonium triflate, sulfonium acetate, sulfonium sulfonate, sulfonium chloride, sulfonium sulfate, sulfonium phosphate, sulfonium thiocyanate, sulfonium dicyanamide, sulfonium benzoate, sulfonium triflate, ammonium acetate, ammonium sulfonate, ammonium chloride, ammonium sulfate, ammonium phosphate, ammonium thiocyanate, ammonium dicyandiamide, ammonium benzoate, ammonium triflate, and mixtures thereof.

[0030] Preferably, the ionic liquid is 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyano. choline amide, 1-ethyl-3-methylimidazolium benzoate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline N-cyclohexylsulfamate, tris(2-hydroxyethyl)methylammonium methylsulfate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, choline acetate, and mixtures thereof.

[0031] More preferably, the ionic liquid is selected from the group consisting of 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, choline trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, choline acetate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1-ethyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, choline saccharinate, choline acesulfamate, and mixtures thereof.

[0032] In one embodiment of the electrically conductive pressure sensitive adhesive composition, two or more ionic liquids are used, and in this embodiment the ionic liquids are selected from the group consisting of 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1 -Ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline N-cyclohexylsulfamate, tris(2-hydroxyethyl)methylammonium methylsulfate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-allyl-3-methylimidazolium 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, choline acetate; preferably, the two or more ionic liquids are selected from the group consisting of 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, choline trifluoromethanesulfonate , 1-ethyl-3-methylimidazolium acetate, choline acetate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-allyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, choline saccharinate, and choline acesulfamate.

[0033] In a particularly preferred embodiment, the ionic liquid is selected from the group consisting of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline N-cyclohexylsulfamate, tris(2-hydroxyethyl)methylammonium methylsulfate , choline acetate and mixtures thereof, and more preferably selected from the group consisting of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline acetate and mixtures thereof.

[0034] Commercially available ionic liquids suitable for use in the present invention include, but are not limited to, Basionics ST80, Basionics Kat1, Basionics BC01, Basionics VS1, Basionics VS03, and Efka IO 6785, all available from BASF.

[0035] The ionic liquid is preferably contained in the conductive pressure-sensitive adhesive composition in an amount of 0.1 to 35% by weight, preferably 0.5 to 25% by weight, and more preferably 1 to 15% by weight, based on the total weight of the composition.

[0036] Preferably, the electrically conductive pressure sensitive adhesive composition comprises: a.2-EHA b.MMA c.2-HEA d.BA e. A compound of formula (I); and an ionic liquid and a copolymer obtained from a reaction mixture comprising:

[0037] Surprisingly, it has been found that the best performance of the electrically conductive pressure sensitive adhesive composition is achieved when an acrylic monomer mixture is used to obtain the copolymer. Thus, in a preferred embodiment, the electrically conductive pressure sensitive adhesive composition comprises: Each based on the total weight of the reaction mixture: a. 2-EHA in an amount of 1 to 20% by weight, preferably 2 to 7% by weight b. MMA in an amount of 1 to 7% by weight, preferably 2 to 5% by weight c. 2-HEA in an amount of 15 to 40% by weight, preferably 20 to 35% by weight d. BA in an amount of 40 to 80% by weight, preferably 55 to 65% by weight e. a compound of formula (I) in an amount of 0.1 to 50% by weight, preferably 0.2 to 30% by weight, in particular 0.5 to 10% by weight; and 0.1 to 35 wt %, preferably 0.5 to 25 wt %, and more preferably 1 to 15 wt % of the ionic liquid, each based on the total weight of the conductive pressure-sensitive adhesive composition. and a copolymer obtained from a reaction mixture comprising:

[0038] In another aspect, the present invention relates to a method for producing an electrically conductive pressure sensitive adhesive composition according to the present invention, the method comprising: a) providing an initial solution and a feed solution of a reaction mixture comprising a monomeric acrylic mixture and a compound of formula (I); b) providing an initial solution and a feed solution of initiator solution; c) adding an initial initiator solution to the initial solution of the reaction mixture at room temperature; d) heating the reaction mixture of step c) to a temperature between 60°C and 120°C, preferably between 70°C and 90°C; e) sequentially adding a feed solution of reaction mixture and a feed solution of initiator solution; Includes.

[0039] In a preferred embodiment, step e) of the method of the present invention is carried out over a period of 2 to 8 hours, preferably 3 to 5 hours.

[0040] The initiator used may be any component suitable for initiating the polymerization of acrylic and styrene monomers. Preferably, the initiator is selected from the group consisting of 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexanecarbonitrile), dimethyl 2,2'-azobis(2-methylpropionate), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), benzoyl peroxide, tert-butyl hydroperoxide, tert-butyl peracetate, tert-butyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl carbonate, cumene hydroperoxide, cyclohexanone peroxide, dicumyl peroxide, and lauroyl peroxide. 2,2'-azobisisobutyronitrile (AIBN) is particularly preferred as the initiator.

[0041] The conductive pressure-sensitive adhesive composition of the present invention is particularly suitable for contact with human skin to monitor bodily functions such as heart rate and brain waves over long periods of time. Therefore, a further object of the present invention is to use the conductive pressure-sensitive adhesive composition of the present invention as a contact medium for dermal applications as part of an electrode for measuring biosignals from the skin, as athletic tape, transdermal drug patches, industrial permanent adhesive tape, and construction permanent adhesive tape. Furthermore, the conductive pressure-sensitive adhesive is also preferably used for safety labels for power equipment, masking tape, price labels, and / or electrochemical peeling applications.

[0042] The present invention also provides a compound of formula (I): [ka] [Wherein R1, R2 and X + are as defined herein] The present invention relates to the compound

[0043] R1 and R2 may both be sulfate groups. Alternatively, one of R1 or R2 is a sulfate group. Preferably, R 1 is a sulfate group and R2 is a hydrogen atom.

[0044] The present invention also provides a method for preparing compounds of formula (I) as defined herein. The method generally involves preparing the free acid corresponding to the compound of formula (I) or its salt equivalent, followed by addition of an appropriate cation (i.e., X + The method involves preparing a free acid form of Compound (I) and converting it into a salt based on an appropriate cation (i.e., X + This method may also include the step of forming a salt of Compound (I) by adding a base where X is the desired cation. This method involves preparing an alternative salt of Compound (I), i.e., where X is different from the desired X, and adding the appropriate cation (i.e., X + The method may also involve carrying out cation exchange with a salt based on a base (wherein is the desired cation) to form a salt of Compound (I).

[0045] An exemplary method for preparing a compound of formula (IA) is: reacting 4-vinylphenol with sulfur trioxide trimethylamine complex to form a reactant mixture; adding tetrabutylammonium hydroxide to the reaction mixture; and formula (IA): [ka] Isolating the compound of Includes.

[0046] As will be appreciated by those skilled in the art, the starting materials and reagents can be substituted as appropriate to prepare other compounds falling within the scope of compounds of formula (I).

[0047] The present invention also provides a compound of formula (I): [ka] wherein R, R and X are monomers in the polymerization process as defined herein. The present invention relates to the use of the compound of the present invention.

[0048] With this disclosure, it will be understood that the present invention can also be described by the following statements:

[0049] 1.a) a monomeric acrylic mixture; and b) Formula (I): [ka] [In the formula, R 1 is a sulfate group (OSO3 - ), sulfonate group (SO3 - ) or a hydrogen atom (H); R 2 is a sulfate group, a sulfonate group, an alkoxy group, or a hydrogen atom and X + is R 1 or R 2 is the sulfate counterion (OSO3- ) is a counterion that satisfies the condition Compounds of 1. An electrically conductive pressure sensitive adhesive composition comprising a copolymer obtained from a reaction mixture comprising:

[0050] 2. R1 is a sulfate group (OSO3 - 2. The electrically conductive pressure-sensitive adhesive composition of claim 1, wherein

[0051] 3. The electrically conductive pressure-sensitive adhesive composition according to statement 2, characterized in that R2 is a hydrogen atom.

[0052] 4. The electrically conductive pressure-sensitive adhesive composition according to statement 2, characterized in that R2 is an alkoxy group.

[0053] 5. R2 is a sulfate group (OSO3 - 2. The electrically conductive pressure-sensitive adhesive composition of claim 1, wherein

[0054] 6. The electrically conductive pressure-sensitive adhesive composition according to statement 5, characterized in that R1 is a hydrogen atom.

[0055] 7. The electrically conductive pressure-sensitive adhesive composition according to statement 5, characterized in that R1 is an alkoxy group.

[0056] 8.X + is NR 3 R 4 R 5 R 6+ and R 3 , R 4 , R 5 and R 6 are each independently selected from C1-C8 alkyl, preferably C2-C6 alkyl, and more preferably X + is N(C4H9)4 + 2. The electrically conductive pressure sensitive adhesive composition of any of the preceding claims, wherein

[0057] 9.X +4. The electrically conductive pressure sensitive adhesive composition of any of the preceding statements, wherein is an optionally substituted imidazolium.

[0058] 10.X + 10. The electrically conductive pressure-sensitive adhesive composition of claim 9, wherein

[0059] 11.X + is a substituted imidazolium, preferably a 1,3-dialkylimidazolium, and each alkyl group is independently selected from linear or branched C1-C6 alkyl, more preferably linear or branched C1-C3 alkyl.

[0060] 12.X + is 1,3-dialkylimidazolium and each alkyl group is independently selected from linear C1-C6 alkyl, preferably linear C1-C3 alkyl.

[0061] 13.X + 10. The electrically conductive pressure-sensitive adhesive composition of claim 9, wherein is 1-ethyl-3-methylimidazolium.

[0062] 14.X + 8. The electrically conductive pressure-sensitive adhesive composition of any one of statements 1 to 7, wherein is choline.

[0063] 15.X + 8. The electrically conductive pressure sensitive adhesive composition of any one of statements 1 to 7, wherein is optionally substituted pyridinium.

[0064] 16.X + 16. The electrically conductive pressure sensitive adhesive composition of statement 15, wherein is pyridinium.

[0065] 17.X +is a substituted pyridinium, preferably a mono- or di-substituted pyridinium, i.e., a pyridinium having substituents at the 1,2 or 1,3 or 1,4 positions on the pyridine ring, more preferably X + is 1-alkylpyridinium, 1,2-alkylpyridinium, 1,3-alkylpyridinium, or 1,4-alkylpyridinium, and each alkyl group is independently selected from linear or branched C1-C6 alkyl, preferably linear or branched C1-C4 alkyl, more preferably linear C1-C4 alkyl.

[0066] 18.X + 8. The electrically conductive pressure sensitive adhesive composition of any one of statements 1 to 7, wherein is optionally substituted pyrrolidinium.

[0067] 19.X + 20. The electrically conductive pressure sensitive adhesive composition of statement 18, wherein

[0068] 20.X + is a substituted pyrrolidinium, preferably a mono- or di-substituted pyrrolidinium, e.g., di-substituted on the nitrogen ring member, more preferably a 1-alkylpyrrolidinium or a 1,1-dialkylpyrrolidinium, and each alkyl group is independently selected from linear or branched C1-C6 alkyl, preferably linear or branched C1-C4 alkyl, more preferably linear C1-C4 alkyl.

[0069] 21.X + 8. The electrically conductive pressure-sensitive adhesive composition according to any one of statements 1 to 7, wherein is phosphonium.

[0070] 22.X + 8. The electrically conductive pressure-sensitive adhesive composition according to any one of statements 1 to 7, wherein is sulfonium.

[0071] 23. Any of the preceding electrically conductive pressure-sensitive adhesive compositions, characterized in that the (meth)acrylic mixture contains at least one of the following: methyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, acrylic acid, C1-C18 alkyl (meth)acrylate, (meth)acrylamide, vinyl acetate, N-vinyl caprolactam, acrylonitrile, vinyl ether, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, glycidyl (meth)acrylate, and mixtures thereof, and is preferably formed from monomers selected from the group consisting of hydroxyethyl acrylate, methyl methacrylate, n-butyl acrylate, 2-ethylhexyl acrylate, and mixtures thereof.

[0072] 24. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the compound of formula (I) is contained in the reaction mixture in an amount of 0.1 to 50% by weight, based on the total weight of the reaction mixture.

[0073] 25. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the compound of formula (I) is contained in the reaction mixture in an amount of 0.2 to 30% by weight, based on the total weight of the reaction mixture.

[0074] 26. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the compound of formula (I) is contained in the reaction mixture in an amount of 0.5 to 10% by weight, based on the total weight of the reaction mixture.

[0075] 27. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 2-EHA in an amount of 1 to 10 wt % based on the total weight of the reaction mixture.

[0076] 28. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 2-EHA in an amount of 2 to 7 wt % based on the total weight of the reaction mixture.

[0077] 29. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains MMA in an amount of 1 to 7 wt % based on the total weight of the reaction mixture.

[0078] 30. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains MMA in an amount of 2 to 5 wt % based on the total weight of the reaction mixture.

[0079] 31. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 15 to 40% by weight of 2-HEA, based on the total weight of the reaction mixture.

[0080] 32. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 2-HEA in an amount of 20 to 35% by weight, based on the total weight of the reaction mixture.

[0081] 33. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 40 to 80% by weight of BA based on the total weight of the reaction mixture.

[0082] 34. Any of the above electrically conductive pressure-sensitive adhesive compositions, characterized in that the reaction mixture contains 55 to 65% by weight of BA based on the total weight of the reaction mixture.

[0083] 35. The pressure-sensitive adhesive composition further preferably comprises 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline N-cyclohexylsulfamate, tris(2-hydroxyethyl)methylammonium methylsulfate, choline acetate, and the like. and mixtures thereof, and more preferably an ionic liquid selected from the group consisting of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline acetate, and mixtures thereof.

[0084] 36. The electrically conductive pressure-sensitive adhesive composition of statement 35, wherein the ionic liquid is present in an amount of 0.1 to 35 wt %, based on the total weight of the pressure-sensitive adhesive composition.

[0085] 37. The electrically conductive pressure-sensitive adhesive composition of statement 35, wherein the ionic liquid is present in an amount of 0.5 to 25 wt %, based on the total weight of the pressure-sensitive adhesive composition.

[0086] 38. The electrically conductive pressure-sensitive adhesive composition of statement 35, wherein the ionic liquid is present in an amount of 1 to 15 wt %, based on the total weight of the pressure-sensitive adhesive composition.

[0087] 39. The composition comprises: Based on the total weight of the reaction mixture, a) 2-EHA in an amount of 1 to 20% by weight, preferably 2 to 7% by weight b) MMA in an amount of 1 to 7% by weight, preferably 2 to 5% by weight c) 2-HEA in an amount of 15 to 40% by weight, preferably 20 to 35% by weight d) BA in an amount of 40 to 80% by weight, preferably 55 to 65% by weight e) a compound of formula (I) in an amount of 0.1 to 50% by weight, preferably 0.2 to 30% by weight, in particular 0.5 to 10% by weight; and 0.1 to 35% by weight, preferably 0.5 to 25% by weight, particularly 1 to 15% by weight, of the ionic liquid, based on the total weight of the conductive pressure-sensitive adhesive composition. 10. The electrically conductive pressure sensitive adhesive composition of claim 9, further comprising a copolymer obtained from a reaction mixture comprising:

[0088] 40. a) providing an initial solution and a feed solution of a reaction mixture comprising a monomeric acrylic mixture and a compound of formula (I); b) providing an initial solution and a feed solution of initiator solution; c) adding an initial initiator solution to the initial solution of the reaction mixture at room temperature; d) heating the reaction mixture of step c) to a temperature between 60°C and 120°C, preferably between 70°C and 90°C; e) sequentially adding a feed solution of reaction mixture and a feed solution of initiator solution; 40. A method for producing the electrically conductive pressure-sensitive adhesive composition according to any one of items 1 to 39, comprising:

[0089] 41. The method of statement 40, wherein the initiator is selected from the group consisting of 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexanecarbonitrile), dimethyl 2,2'-azobis(2-methylpropionate), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), benzoyl peroxide, tert-butyl hydroperoxide, tert-butyl peracetate, tert-butyl peroxide, tert-butyl peroxybenzoate, tert-butylperoxyisopropyl carbonate, cumene hydroperoxide, cyclohexanone peroxide, dicumyl peroxide, and lauroyl peroxide.

[0090] 42. Use of the pressure-sensitive adhesive composition of any of statements 1 to 39 in skin applications, as a contact medium as part of an electrode for measuring biosignals from the skin, athletic tape, transdermal drug patches, permanent adhesive tapes for industrial and construction work, and / or as a safety label for power equipment, masking tape, price label, and / or electrochemical release agent.

[0091] 43. Compounds of formula (I): [ka] [In the formula, R 1 is a sulfate group (OSO3 - ), sulfonate group (SO3 - ) or a hydrogen atom (H); R 2 is a sulfate group, a sulfonate group, an alkoxy group, or a hydrogen atom and X + is R 1 or R 2 is the sulfate counterion (OSO3 - ) is a counterion that satisfies the condition.

[0092] 44. R1 is a sulfate group (OSO3 - 44. The compound according to statement 43, wherein

[0093] 45. The compound according to statement 44, characterized in that R2 is a hydrogen atom.

[0094] 46. ​​The compound according to statement 44, characterized in that R2 is an alkoxy group.

[0095] 47. R2 is a sulfate group (OSO3 - 44. The compound according to statement 43, wherein

[0096] 48. The compound according to statement 47, characterized in that R1 is a hydrogen atom.

[0097] 49. The compound according to statement 47, characterized in that R1 is an alkoxy group.

[0098] 50.X + But NR 3 R 4 R 5 R 6+ and R 3 ,R 4 ,R 5 and R 6 are each independently C1-C8 alkyl, preferably C2-C6 alkyl, and more preferably X + is N(C4H9)4 + 50. The compound according to any one of statements 43 to 49, wherein

[0099] 51.X + 51. The compound according to any one of statements 43 to 50, wherein is an optionally substituted imidazolium.

[0100] 52.X + 52. The compound according to statement 51, wherein is imidazolium.

[0101] 53.X +is a substituted imidazolium, preferably a 1,3-dialkylimidazolium, wherein each alkyl group is independently selected from linear or branched C1-C6 alkyl, more preferably linear or branched C1-C3 alkyl.

[0102] 54.X + 54. The compound according to statement 53, wherein: is 1,3-dialkylimidazolium; and each alkyl group is independently selected from straight chain C1-C6 alkyl, preferably straight chain C1-C3 alkyl.

[0103] 55.X + 54. The compound according to statement 53, wherein is 1-ethyl-3-methylimidazolium.

[0104] 56.X + 56. The compound according to statements 43 to 55, wherein is choline.

[0105] 57.X + 57. The compound according to statements 43 to 56, wherein is an optionally substituted pyridinium.

[0106] 58.X + 58. The compound according to statement 57, wherein is pyridinium.

[0107] 59.X + is a substituted pyridinium, preferably a mono- or di-substituted pyridinium, i.e., a pyridinium having substituents at the 1,2 or 1,3 or 1,4 positions on the pyridine ring, more preferably X + is 1-alkylpyridinium, 1,2-alkylpyridinium, 1,3-alkylpyridinium, or 1,4-alkylpyridinium, and each alkyl group is independently selected from straight or branched chain C1-C6 alkyl, preferably straight or branched chain C1-C4 alkyl, more preferably straight chain C1-C4 alkyl.

[0108] 60.X + 60. The compound of any one of statements 43 to 59, wherein is optionally substituted pyrrolidinium.

[0109] 61.X + 61. The compound according to claim 60, wherein is pyrrolidinium.

[0110] 62.X + is a substituted pyrrolidinium, preferably a mono-N-substituted pyrrolidinium or a di-substituted pyrrolidinium, e.g., di-substituted on the nitrogen ring member, more preferably a 1-alkylpyrrolidinium or a 1,1-dialkylpyrrolidinium, and each alkyl group is independently selected from straight or branched C1-C6 alkyl, preferably straight or branched C1-C4 alkyl, more preferably straight chain C1-C4 alkyl.

[0111] 63.X + 63. The compound according to any one of statements 43 to 62, wherein is phosphonium.

[0112] 64.X + 64. The compound according to any one of statements 43 to 63, wherein is sulfonium.

[0113] 65. The following formula (IA): [ka] 44. The compound of statement 43 having the formula:

[0114] 66. Use of a compound as defined in any of statements 43 to 65 for use as a monomer in a polymerization process.

[0115] The present invention will be described in more detail below with reference to examples, but these examples are not intended to limit the scope or spirit of the present invention.

[0116] Example 1: i) a compound of the following formula (IA), hereinafter abbreviated as SS (styrene sulfate): [ka] Preparation of the monomer

[0117] The reaction was carried out in a three-neck flask equipped with a reflux condenser and a magnetic stirrer. Under nitrogen, 4-vinylphenol (4-VP, 6.0 g, 50.0 mmol) and sulfur trioxide trimethylamine complex (SO3NMe, 10.5 g, 75.0 mmol, 1.5 equiv.) were added to the flask and dissolved in 60 mL of anhydrous DMF. The reaction was stirred at an oil bath temperature of 80 °C for 72 h.

[0118] The reaction was cooled to room temperature, and 1.1 equivalents of tetrabutylammonium hydroxide (TBAOH, 40% aqueous solution) was added and stirred for 1 hour. Additional water was added, and the solution was extracted with DCM. The solvent was evaporated, and the product was purified by column chromatography with 95:5 DCM:MeOH. The product was dried in vacuo and solidified to an off-white solid. Isolated yield of SS: 60%.

[0119] Example 2: i) Preparation of Conductive Pressure Sensitive Adhesive (PSA) Compositions

[0120] The compositions in Table 1 were prepared as follows: The initiator solution was added to an initial monomer acrylic mixture containing 2-EHA, MMA, 2-HEA, BA, and the compound of formula (IA) above, and heated to 80°C with stirring. Additional solutions of the monomer acrylic mixture and the initiator solution were added sequentially. The mixture was then cooled to room temperature and diluted with ethanol, isopropanol, and ethyl acetate to obtain the final polymer solution.

[0121] [Table 1]

[0122] ii) Preparation of PSA films and impedance measurement procedures PSA films for property testing were prepared by casting films of each polymer solution onto silicone paper. After coating, the films were dried in an oven at 115°C for 5 minutes and then covered with silicone paper. A is 30g / m 2 The film thickness was adjusted to 2x2cm. Two test pieces of 2x2cm were applied to each polymer solution. The two substrates were then bonded together at a 180° angle and a potentiostat was used to measure the film thickness. 6 Impedance measurements were performed in the frequency range Hz≦ν≦0.1 Hz. The resistivity ρ was calculated using the measured impedance Z, the overlap area A, and the layer thickness d according to Equation 1:

number

[0123] iii) Resistivity reduction by compounds of formula (I) The data collected from the impedance measurements are shown in Table 2 and visualized in Figure 1. The resistivity of PSA decreases as the content of the compound of formula (I) increases. Since conductivity is defined as the inverse resistance, the conductivity increases as the content of the compound of formula (I) increases. This is advantageous for applications in the electronics and medical industries, such as ECG medical patches. As is evident from the data in Figure 1, the resistivity decreases as the SS content increases.

[0124] [Table 2]

[0125] Example 3: i) Preparation of polymer-ionic liquid blends Polymer solutions were prepared as described in Example 2. Polymer-ionic liquid blends were prepared by adding the ionic liquid (IL) 1-ethyl-3-methylimidazolium triflate. Blends containing 5 wt % or 10 wt % ionic liquid based on the solid content of the polymer solution were prepared.

[0126] ii) Preparation of PSA film for peel test PSA films for property testing were prepared by coating each polymer solution onto etched polyethylene foil. After coating, the films were dried in an oven at 115°C for 5 minutes and then covered with silicone paper. The film thickness was adjusted to achieve a coating weight of ρ A is 30g / m 2 A film of

[0127] iii) Preparation and procedure of 180° peel test samples The 180° peel test was carried out according to protocol FTM1 defined by the European Adhesive Label Industry Association (FINAT).

[0128] Data collected from 180° peel tests of polymer-ionic liquid blends are presented in Table 3 and visualized in Figure 2. The presence of the compound of formula (I) in the polymer improves the adhesion of PSAs to stainless steel and glass substrates without and with 5 wt% IL. Peel strength increases as the content of the compound of formula (I) increases, a desirable outcome for high-performance PSAs. Figure 2 summarizes the 180° peel test evaluations 24 hours after application to stainless steel (Figure 2a) and glass (Figure 2b). Tests were conducted using the crude polymer solution (left) and polymer-ionic liquid blends containing 5 wt% IL (right), as well as 0 (solid), 0.5 (diagonal), 1.5 (horizontal), and 5 wt% (cross) of the compound of formula (I). As is evident from the data provided, peel strength increases with increasing content of the compound of formula (I) on both substrates with and without IL.

[0129] [Table 3]

[0130] iv) Synergistic effect of SS and IL on substrate wettability Data collected from 180° peel tests of polymer-ionic liquid blends are presented in Table 4 and visualized in Figure 3. In the absence of the comonomer of formula (I) in the polymer, the adhesive takes longer to reach maximum strength, regardless of the addition of ionic liquid, as indicated by the large difference in peel strength measured 20 minutes and 24 hours after application. Similar observations were made for polymers containing 5 wt.% of the compound of formula (I) but no ionic liquid. However, when an IL was added to the polymer containing the comonomer of formula (I), the peel strength at 20 minutes after application increased significantly compared to the previously described system. Near-maximum peel strength was reached after 20 minutes. This observation indicates a synergistic effect between the presence of the comonomer of formula (I) in the polymer and the IL, which has a beneficial impact on the wetting process in terms of shortening application time.

[0131] Figure 3 shows the 180° peel test evaluation data for polymer-ionic liquid blends on stainless steel. Tests were performed after application of 0, 5, and 10 wt% IL and 0 wt% Formula (I) compound (Figure 3a) and 10 wt% Formula (I) compound (Figure 3b) at 20 minutes (solid line) and 24 hours (dotted line). A significant difference in peel strength is observed over time in the absence of Formula (I) comonomer and IL. With Formula (I) and IL comonomer, the maximum peel strength was achieved after 20 minutes, demonstrating the synergistic effect of the presence of Formula (I) comonomer and IL in the polymer on substrate wetting by the polymer.

[0132] [Table 4]

[0133] The data provided not only demonstrate the improved adhesive properties of the conductive pressure-sensitive adhesive compositions of the present invention, but also demonstrate the synergistic effects that can be achieved by combination with ionic liquids.

Claims

1. a) an acrylic mixture of monomers; and b) Formula (I): 【Chemical 1】 [In the formula, R １ is a sulfate group (OSO ３ － ), sulfonate group (SO ３ － ) or a hydrogen atom (H); R ２ is a sulfate group, a sulfonate group, an alkoxy group, or a hydrogen atom; and X ＋ is R １ or R ２ is the sulfate counterion (OSO ３ － ) is a counter ion that satisfies the condition Compounds of 1. An electrically conductive pressure sensitive adhesive composition comprising a copolymer obtained from a reaction mixture comprising:

2. R1 is a sulfate group (OSO ３ － 2. The electrically conductive pressure-sensitive adhesive composition of claim 1, wherein

3. 3. The electrically conductive pressure-sensitive adhesive composition according to claim 2, wherein R2 is a hydrogen atom.

4. R2 is a sulfate group (OSO ３ － 3. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein

5. X ＋ is NR ３ R ４ R ５ R ６＋ and R ３ , R ４ , R ５ and R ６ are each independently C １ -C ８ Alkyl, preferably C ２ -C ６ 5. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the imidazolium group is selected from alkyl, optionally substituted imidazolium, preferably 1-ethyl-3-methylimidazolium, choline, optionally substituted pyridinium, optionally substituted pyrrolidinium, phosphonium, sulfonium and mixtures thereof.

6. X ＋ is NR ３ R ４ R ５ R ６＋ and R ３ , R ４ , R ５ and R ６ are each independently C ２ -C ６ 6. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the alkyl group is selected from alkyl.

7. X ＋ is N(C ４ H ９ ) ４ ＋ The electrically conductive pressure-sensitive adhesive composition according to any one of claims 1 to 6, wherein

8. 8. The electrically conductive pressure-sensitive adhesive composition according to claim 1 , wherein the (meth)acrylic mixture comprises at least one of the following: methyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, acrylic acid, C1-C18 alkyl (meth)acrylate, (meth)acrylamide, vinyl acetate, N-vinyl caprolactam, acrylonitrile, vinyl ether, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, glycidyl (meth)acrylate, and mixtures thereof, and is preferably formed from monomers selected from the group consisting of hydroxyethyl acrylate, methyl methacrylate, n-butyl acrylate, 2-ethylhexyl acrylate, and mixtures thereof.

9. 9. The electrically conductive pressure-sensitive adhesive composition according to claim 1 , wherein the compound of formula (I) is present in the reaction mixture in an amount of 0.1 to 50% by weight, preferably 0.2 to 30% by weight, in particular 0.5 to 10% by weight, based on the total weight of the reaction mixture.

10. 10. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the reaction mixture comprises 2-EHA in an amount of 1 to 10% by weight, preferably 2 to 7% by weight, based on the total weight of the reaction mixture.

11. 11. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the reaction mixture comprises MMA in an amount of 1 to 7 wt. %, preferably 2 to 5 wt. %, based on the total weight of the reaction mixture.

12. 12. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the reaction mixture comprises 2-HEA in an amount of 15 to 40 wt. %, preferably 20 to 35 wt. %, based on the total weight of the reaction mixture.

13. 13. The electrically conductive pressure-sensitive adhesive composition according to claim 1, wherein the reaction mixture comprises 40 to 80 wt. %, preferably 55 to 65 wt. %, of BA, based on the total weight of the reaction mixture.

14. The pressure-sensitive adhesive composition preferably further comprises 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline N-cyclohexylsulfamate, tris(2-hydroxyethyl)methylammonium methylsulfate, choline acetate, and mixtures thereof.

14. The electrically conductive pressure-sensitive adhesive composition according to any one of claims 1 to 13, characterized in that it comprises an ionic liquid selected from the group consisting of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methanesulfonate, 1-ethyl-3-methylimidazolium chloride, 1-ethyl-3-methylimidazolium sulfate, 1-ethyl-3-methylimidazolium diethylphosphate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium dicyanamide, 1-ethyl-3-methylimidazolium benzoate, 1-ethyl-3-methylimidazolium tetrafluoroborate, choline trifluoromethanesulfonate, choline saccharinate, choline acesulfamate, choline acetate, and mixtures thereof.

15. 15. The electrically conductive pressure-sensitive adhesive composition according to claim 14, characterized in that the ionic liquid is present in an amount of 0.1 to 35 wt. %, preferably 0.5 to 25 wt. %, in particular 1 to 15 wt. %, based on the total weight of the pressure-sensitive adhesive composition.

16. The composition comprises: Based on the total weight of the reaction mixture, a) 2-EHA in an amount of 1 to 20% by weight, preferably 2 to 7% by weight b) MMA in an amount of 1 to 7% by weight, preferably 2 to 5% by weight c) 2-HEA in an amount of 15 to 40% by weight, preferably 20 to 35% by weight d) BA in an amount of 40 to 80% by weight, preferably 55 to 65% by weight e) a compound of formula (I) in an amount of 0.1 to 50% by weight, preferably 0.2 to 30% by weight, in particular 0.5 to 10% by weight; and 0.1 to 35% by weight, preferably 0.5 to 25% by weight, especially 1 to 15% by weight, of an ionic liquid, based on the total weight of the pressure-sensitive adhesive composition 16. The electrically conductive pressure sensitive adhesive composition according to claim 1, comprising a copolymer obtained from a reaction mixture comprising:

17. a) providing an initial solution and a feed solution of a reaction mixture comprising a monomeric acrylic mixture and a compound of formula (I); b) providing an initial solution and a feed solution of initiator solution; c) adding the initial initiator solution to the initial solution of the reaction mixture at room temperature; d) heating the reaction mixture of step c) to a temperature between 60°C and 120°C, preferably between 70°C and 90°C; e) sequentially adding a feed solution of reaction mixture and a feed solution of initiator solution; 17. A method for producing the electrically conductive pressure sensitive adhesive composition of claim 1, comprising:

18. 18. The process of claim 17, wherein the initiator is selected from the group consisting of 2,2'-azobisisobutyronitrile, 1,1'-azobis(cyclohexanecarbonitrile), dimethyl 2,2'-azobis(2-methylpropionate), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), benzoyl peroxide, tert-butyl hydroperoxide, tert-butyl peracetate, tert-butyl peroxide, tert-butyl peroxybenzoate, tert-butylperoxyisopropylcarbonate, cumene hydroperoxide, cyclohexanone peroxide, dicumyl peroxide, and lauroyl peroxide.

19. 17. Use of a pressure-sensitive adhesive composition according to any one of claims 1 to 16 as a contact medium in skin applications as part of an electrode for measuring biological signals from the skin, in athletic tapes, transdermal drug patches, permanent adhesive tapes for industrial and construction work, and / or as safety labels for power equipment, masking tapes, price labels, and / or as an electrochemical release agent.

20. Compounds of formula (I): 【Chemistry 2】 [Wherein R1, R2 and X ＋ is as defined in claims 1 to 7].

21. Formula (IA): 【Chemistry 3】 21. The compound of claim 20, having the formula:

22. 22. Use of a compound as defined in claim 20 or claim 21 for use as a monomer in a polymerization process.

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