Electrically debondable adhesive articles

Abstract

The present disclosure provides a polymerizable composition including: a) a C1-C18 alkyl (meth)acrylate ester monomer; b) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components; c) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components; and d) an ionic liquid. Additionally, an at least partially polymerized reaction product of the polymerizable composition and a pressure sensitive adhesive article are provided. The adhesive article is electrically debondable. Further, another polymerizable composition is provided including specific polymerizable ionic liquid(s). Another polymerizable composition includes a C1-C18 alkyl (meth)acrylate ester monomer and an ionic liquid and is essentially free of a carboxylic acid-containing (meth)acrylate monomer.

Description

PA102937W003ELECTRICALLY DEBONDABLE ADHESIVE ARTICLESField

[0001] The present disclosure generally relates to the field of electrically debondable adhesives.Background

[0002] New adhesives are needed for use in the preparation of electronic devices and in various industrial applications. For example, in electronic devices, particularly mobile electronic devices (e.g., hand-held, or wearable electronic devices), various adhesives such as pressure sensitive adhesives are used to bond the cover glass (or lens) to the underlying display module, bond the touch sensor to the cover glass and display, or bond the lower components of the display to the housing. The selected adhesive typically should have sufficiently high adhesive strength to properly maintain good adhesion to those components, not only when the mobile electronic devices are operating under normal conditions, but also when they are subjected to traumatic forces (e.g., when impacted and / or dropped onto a hard surface).

[0003] Further, new adhesives are needed for electronic devices that can perform well during the lifetime of the devices but that can be removed (e.g., debonded) from the electronic components after the useful lifetime of the device or to repair the device to extend its useful lifetime. The removal of the adhesives is preferably clean so that the electronic components can be reused or recycled, or so that the electronic device can be repaired. Additionally, debonding enables reworking of mistakes made during manufacturing before a device is fully assembled using the adhesives.Brief Description of Drawings

[0004] FIG. 1 A is a schematic cross-sectional view of an exemplary tape, according to some embodiments of the present disclosure.

[0005] FIG. 1B is a schematic cross-sectional view of an exemplary tape including two liners, according to some embodiments of the present disclosure.

[0006] FIG. 2 is a representation of the experimental setup for the Tensile Pushout Test Method.

[0007] Repeated use of reference characters in the specification and drawings is intended to represent the same or analogous features or elements of the disclosure. It should be understood that numerous other modifications and embodiments can be devised by those skilled in the art, which fall within the scope and spirit of the principles of the disclosure. The figures may not be drawn to scale.Summary

[0008] In a first aspect, a polymerizable composition is provided. The polymerizable composition comprises a) a C1-C18 alkyl (meth)acrylate ester monomer; b) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer; c) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group; and d) an ionic liquid. The wt.% of each of component b) and component c) is based on a total weight of polymerizable components. The ionic liquid may comprise functionality of the first nitrogen-containing monomer to provide both component b) and component d) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component c) and component d).

[0009] In a second aspect, an at least partially polymerized reaction product is provided. The at least partially polymerized reaction product is of the polymerizable composition according to any embodiment of the first aspect.

[0010] In a third aspect, a pressure sensitive adhesive article is provided. The pressure sensitive adhesive article comprises an adhesive composition comprising the at least partially polymerized reaction product of the second aspect. The adhesive composition is disposed on at least a portion of a substrate.

[0011] In a fourth aspect, another polymerizable composition is provided. The polymerizable composition comprises an adhesive precursor and a polymerizable ionic liquid of Formula I and / or of Formula II. In the formulas, Ri is independently H or methyl, and R₂ and R₃ are each independently linear or branched alkyl groups and / or ethoxy groups.

[0012] In a fifth aspect, an additional polymerizable composition is provided. The polymerizable composition comprises a C1-C18 alkyl (meth)acrylate ester monomer and an ionic liquid. The polymerizable composition is essentially free of a carboxylic acid-containing (meth)acrylate monomer.

[0013] The above summary is not intended to describe each embodiment. The details of one or more embodiments are also set forth in the description below. Other features, objects, and advantages will be apparent from the description and from the claims.Detailed Description

[0014] The terms “a”, “an”, “the”, “at least one”, and “one or more” are used interchangeably.

[0015] The term “and / or” means one or both such as in the expression A and / or B refers to A alone. B alone, or to both A and B.

[0016] The term "essentially” means 95% or more.

[0017] The term "alkyl” refers to a monovalent radical of an alkane. Suitable alkyl groups can have up to 50 carbon atoms, up to 40 carbon atoms, up to 30 carbon atoms, up to 20 carbon atoms, up to 16 carbon atoms, up to 12 carbon atoms, up to 10 carbon atoms, up to 8 carbon atoms, up to 6 carbon atoms, up to 4 carbon atoms, or up to 3 carbon atoms. The alkyl groups can be linear, branched, cyclic, or a combination thereof. Linear alkyl groups often have 1 to 30 carbon atoms, 1 to 20 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. Branched alkyl groups often have 3 to 50 carbon atoms, 3 to 40 carbon atoms. 4 to 20 carbon atoms, 3 to 10 carbon atoms, or 3 to 6 carbon atoms. Cyclic alkyl groups often have 3 to 50 carbon atoms, 5 to 40 carbon atoms, 6 to 20 carbon atoms, 5 to 10 carbon atoms, or 6 to 10 carbon atoms.

[0018] The term “alkylene” refers to a divalent group that is a radical of an alkane. The alkylene can be straight-chained, branched, cyclic, or combinations thereof. The alkylene typically has 1 to 20 carbon atoms. In some embodiments, the alkylene contains 4 to 14 carbon atoms, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. The radical centers of the alkylene can be on the same carbon atom (i.e., an alkylidene) or on different carbon atoms. In certain embodiments, the alkylene can be substituted with an OH group.

[0019] The term “hydroxy I group” means a monovalent group of formula -OH.

[0020] The term “aryl” refers to a monovalent group that is radical of an arene, which is a carbocyclic, aromatic compound. The aryl can have one to five rings that are connected to or fused to the aromatic ring. The other ring structures can be aromatic, non-aromatic, or combinations thereof. Examples of aiyl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, acenaphthyl, anthraquinonyl, phenanthryl, anthracenyl, pyrenyl, perylenyl, and fluorenyl.

[0021] The term “aralkyl” refers to a monovalent group of formula -R-Ar where R is an alkylene and Ar is an aryl group. That is, the aralkyl is an alkyl substituted with an aryl.

[0022] The term “aralkylene” refers to a divalent group of formula -R-Ara- where R is an alkylene and Arais an arylene (i.e., an alkylene is bonded to an arylene).

[0023] The term “arylene” refers to a divalent group that is carbocyclic and aromatic. The group has one to five rings that are connected, fused, or combinations thereof. The other rings can be aromatic, non-aromatic, or combinations thereof. In some embodiments, the arylene group has up to 5 rings, up to 4 rings, up to 3 rings, up to 2 rings, or one aromatic ring. For example, the arylene group can be phenylene. The term “alkarylene” refers to a divalent group that is an arylene group substituted with an alkyl group or an arylene group attached to an alkylene group. Unless otherwise indicated, the alkarylene group typically has from 1 to 20 carbon atoms, 4 to 14 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbonatoms, or 1 to 4 carbon atoms. Unless otherwise indicated, for both groups, the alkyl or alkylene portion typically has from 1 to 20 carbon atoms, 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms. Unless otherwise indicated, for both groups, the aryl or arylene portion typically has from 6 to 20 carbon atoms, 6 to 18 carbon atoms. 6 to 16 carbon atoms, 6 to 12 carbon atoms, or 6 to 10 carbon atoms. In certain embodiments, the arylene group or the alkarylene group has 4 to 14 carbon atoms.

[0024] The term “(meth)acrylate” means acrylate or methacrylate.

[0025] The term “(meth)acryloyl” refers to a group of formula CH2=CR-(C=O)- where R is hydrogen (for an acryloyl group) or methyl (for a methacryloyl group).

[0026] As used herein, the term “macromer” refers to a monomer having a polymeric group. A macromer is a subset of the term “monomer”.

[0027] The term “monomeric unit” refers to the reaction product of a polymerizable component (i.e., a monomer (including a macromer)) within the (meth)acrylate copolymer. As an example, the monomeric unit of acrylic acidH HH₂C=CH *–C–C–*‖=O H ‖=OOH is OHwhere the asterisks (*) indicate the attachment site to another group such as another monomeric unit or terminal group in the (meth)acrylate copolymer.

[0028] The term “(meth)acrylate macromer” refers to a monomer having a single (meth)acryloyloxy group (i.e., a group of formula CH2=CR-(CO)-O- where R is hydrogen or methyl) plus a polyethylene oxide) group, poly(propylene oxide) group, polyethylene oxide-co-propylene oxide) group, poly(ethylene oxide-block-propylene oxide) group, poly(propylene-co-butylene oxide) group, poly(tetrahydrofuran) group, or poly(ester) group.

[0029] The term “poly(ethylene oxide) group” refers to a group that contains at least 3 ethylene oxide (-(C2H4O)-) groups and the term “polypropylene oxide) group” refers to a group that contains at least 3 propylene oxide (–(C₃H₆O)– groups. The term “poly(butylene oxide) group” refers to a group that contains at least 3 butylene oxide (-(C4H8O)-) groups.

[0030] The term “polyethylene oxide-co-propylene oxide) group” contains at least 3 monomer units of some combination of ethylene oxide groups and propylene oxide groups. The polyethylene oxide-co-propylene oxide) group is a copolymeric group.

[0031] The term “poly(tetrahydrofuran) (meth)acrylate macromer” refers to a monomer having a single (meth)acryloyloxy group (i.e., a group of formula CH2=CR-(CO)-O- where R is hydrogen or methyl) plus a poly(tetrahydrofuran) group that contains at least three –(C₄H₈O)– groups. The term “poly(tetrahydrofuran)” can be used interchangeably with the terms “poly(tetramethylene

[0032] oxide)” and “poly(tetramethylene glycol)”.

[0033] The term “polyester” refers to repeating difunctional polymer wherein the repeat units are joined by ester linkages. Ester groups have the general formula -R — C(O) — OR’. The term “poly ether” refers to repeating difunctional alkoxy radicals having the general formula -O-R-. Preferred R and R’ groupshave the general formula –CₙH₂ₙ– and include, for example, methylene, ethylene, propylene (including n-propylene and i-propylene) and butylene, or a combination thereof. Combinations of R and R’ groups may be provided, for example, as random or block type copolymers.

[0034] The term “ambient temperature” refers to a temperature in the range of 20 degrees Celsius to 25 degrees Celsius, inclusive.

[0035] The terms “cure” and “curable” refer to joining polymer chains together by covalent chemical bonds, usually via crosslinking molecules or groups, to form a network polymer. Therefore, in this disclosure the terms “cured” and “crosslinked” may be used interchangeably. A cured or crosslinked polymer is generally characterized by insolubility, but may be swellable in the presence of an appropriate solvent.

[0036] The term “polymerizable component” refers to any material (e.g., monomers, crosslinkers, oligomers, macromers, prepolymers, polymers, etc.) that participates in a curing or crosslinking reaction in forming a polymer and / or crosslinked polymer.

[0037] The term “resin” with respect to “parts per hundred parts resin” refers to 100 parts of the total polymerizable components.

[0038] The term “backbone” refers to the main continuous chain of a polymer.

[0039] The term “substantially”, unless otherwise specifically defined, means to a high degree of approximation (e.g., within + / - 10% for quantifiable properties) but again without requiring absolute precision or a perfect match. Terms such as same, equal, uniform, constant, strictly, and the like, are understood to be within the usual tolerances or measuring error applicable to the specific circumstance rather than requiring absolute precision or a perfect match.

[0040] By definition, the total weight percentages of all ingredients in a composition equals 100 weight percent.

[0041] The term “film” or "layer” refers to a single stratum within a multilayer film or article.

[0042] The term “substrate” encompasses films, layers, and articles.

[0043] As used herein, “thickness” refers to the smallest dimension of a film or layer, e.g., in a z-axis while a major surface of the film or layer is in the x- and y-axes. Thickness may be determined using a micrometer gauge or doing a microscopic analysis of a cross-sectional sample of a layer or an article.

[0044] Electronics bonding customers desire the ability to debond pressure sensitive adhesives (“PSAs”) by applying an electrical current to the substrates in contact with the PSA. Applying a voltage to the substrates in contact with the adhesive should significantly lower the adhesion force and result in clean separation (i.e., no cohesive failure) from the substrates such that they can be recovered rapidly.

[0045] Polymerizable Compositions

[0046] In a first aspect, a polymerizable composition is provided. The polymerizable composition comprises:

[0047] a) a C1-C18 alkyl (meth)acrylate ester monomer;

[0048] b) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components;

[0049] c) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components; and

[0050] d) an ionic liquid, with the proviso that the ionic liquid may comprise functionality of the first nitrogen-containing monomer to provide both component b) and component d) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component c) and component d).

[0051] Additionally, one or more optional components may also be included in a polymerizable composition, for instance and without limitation, an ethoxy group-containing (meth)acrylate monomer, at least one additive, a filler, a carboxylic acid-containing (meth)acrylate monomer, a (meth) aery late macromer. a crosslinker, or any combinations thereof.

[0052] In some cases, the polymerizable composition contains less than 0.1 wt.% of a hydroxylcontaining (meth)acrylate monomer, based on a total weight of polymerizable components. It is to be noted that this only applies to lower chain hydroxy monomers (e.g., 2-hydroxyethyl acry late and 2-hydroxy butyl acrylate), such as monomers having a molecular weight below 300 Daltons. This is in contrast to longer chain monomers or macromers that have hydroxy end functionality, such as monomers and / or macromers having a molecular weight above 300 Daltons. In such cases that there are essentially no hydroxy monomers, it is to be understood that tire first nitrogen-containing monomer will not be N-hydroxy ethyl acrylamide (NHEA).

[0053] Advantageously, polymerizable compositions according to at least certain embodiments of the present disclosure may be used to prepare electrically debondable adhesive articles. It has been found that polymerization of a polymerizable composition including as the only nitrogen-containing monomer a nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group tends to result in an exothermic reaction such that the amount of heat generated is sufficient to undesirably damage certain adhesive substrates such as liners, more specifically (e.g., substrates having a lower range of their melting points of 80 °C or less). In contrast, it has been unexpectedly discovered that including another nitrogen-containing monomer that is an acrylamide decreases the heat of the exothermic reaction, plus the resulting adhesive exhibits good electrical debondability, yet also has a good balance of peel and high temperature shear adhesion, even in the presence of an ionic liquid which can lead to plasticization and poor shear adhesion, especially at high temperatures. To meet the demanding requirements of the electronics and industrial markets, debondable adhesives must have a balance of electrical debonding, peel and shear adhesion amongst other tests. Using only acrylamide monomers (especially mono or disubstituted acrylamide monomers) results in far inferior high temperature shear resistance, which is even further impaired by the presence of a loose ionic liquid. However, the combination of acrylamide and N-vinyl type monomers with ionic liquids overcomes these limitations.

[0054] The various components of such polymerizable compositions are described below.

[0055] Cl-Cl 8 Alkyl (Meth) acrylate Ester Monomer

[0056] Polymerizable compositions according to the present disclosure include a C1-C18 alkyl (meth)acrylate ester monomer. The C1-C18 alkyl (meth)acrylate ester monomer is a polymerizable component.

[0057] Suitable exemplary alkyl (meth)acrylate ester monomers include for instance and without limitation, iso-octyl acrylate, ethyl acrylate, isopropyl acrylate, isoamyl acry late, sec-butyl acrylate, n-butyl acrylate, 2-methylbutyl acrylate, methyl acrylate, 4-methyl-2-pentyl acrylate. 2-ethylhexyl acrylate, isooctyl acrylate, 2-ethylhexyl methacrylate, n-hexyl acrylate, n-octyl acrylate. 6-methylheptyl acrylate, and mixtures thereof. In certain embodiments, the C1-C18 alkyl (meth)acrylate ester monomer comprises at least one of 2-ethylhexyl acrylate, n-butyl acrylate, 2-methylbutyl acrylate, n-hexyl acrylate, or 6-methylheptyl acrylate.

[0058] Often, the C1-C18 alkyl (meth)acrylate ester monomer is present in an amount of 15 wt.% or greater, based on a total weight of polymerizable components, such as 20 wt.%, 25 wt.%, 30 wt.%, 35 wt.%, 40 wt.%, 45 wt.%, 50 wt.%, 55 wt.%, 60 wt.%, 65 wt.%, or 70 wt.% or greater, based on a total weight of polymerizable components; and 90 wt.% or less, based on a total weight of polymerizable components, such as 85 wt.%, 80 wt.%, 75 wt.%, 70 wt.%, 65 wt.%, 60 wt.%, 55 wt.%, 50 wt.%, 45 wt.%, 40 wt.%, 35 wt.%, or 30 wt.% or less, based on a total weight of polymerizable components.

[0059] In some embodiments, the C1-C18 alkyl (meth)acrylate ester monomer comprises a C8 acrylate in an amount of 30 wt.% or greater, based on a total weight of polymerizable components, such as 35 wt.%, 40 wt.%, 45 wt.%, 50 wt.%, 55 wt.%, 60 wt.%, 65 wt.%, 70 wt.%, 75 wt.%, 80 wt.%, or 85 wt.% or greater, based on a total weight of polymerizable components; and 90 wt.% or less, based on a total weight of polymerizable components. In certain cases, the C1-C18 alkyl (meth)acrylate ester monomer comprises a C8 acrylate in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

[0060] In some embodiments, the C1-C18 alkyl (meth)acrylate ester monomer comprises a C6-C18 (meth)acrylate ester monomer present in an amount of 30 wt.% or greater, based on a total weight of polymerizable components, such as 35 wt.%, 40 wt.%, 45 wt.%, 50 wt.%, 55 wt.%, 60 wt.%, 65 wt.%, 70 wt.%, 75 wt.%, 80 wt.%, or 85 wt.% or greater, based on a total weight of polymerizable components; and 90 wt.% or less, based on a total weight of polymerizable components. In certain cases, the C1-C18 alkyl (meth)acrylate ester monomer comprises a C6-C18 (meth)acrylate ester monomer present in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

[0061] First Nitrogen-Containing Monomer

[0062] Polymerizable compositions according to the present disclosure include a first nitrogencontaining monomer that is an acrylamide monomer. The first nitrogen-containing monomer is a polymerizable component.

[0063] Suitable examples of aery lam ide monomers for use as the first nitrogen-containing monomer include for instance and without limitation, N, N-dimethylacrylamide (NNDMA), N, N-diethylacrylamide (NNDEA), N,N-dimethylaminopropyl acrylamide (DMAPACM), N-tert-octyl-acrylamide (NTOA), N-octyl-acrylamide (NOA). acrylamide (Acm), 4-acryloylmorpholine (ACMO). N-isopropylacrylamide, (NIP AM). N-hydroxyethyl acrylamide (NHEA). N-(isobutoxymethyl)acrylamide (NIBMA). N-tert-butylacrylamide (NTBA), N-(3-methoxypropyl)acrylamide (NMPA), a combinations thereof.

[0064] The first nitrogen-containing monomer is present in an amount of 5 wt.% or greater, based on a total weight of polymerizable components, such as 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%. 13 wt.%, 14 wt.%. 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, or 20 wt.%, based on a total weight of polymerizable components; and 30 wt.% or less, based on a total weight of polymerizable components, 28 wt.%, 26 wt.%, 25 wt.%, 24 wt.%. 22 wt.%, 20 wt.%. 18 wt.%, 16 wt.%, 15 wt.%, 14 wt.%, 12 wt.%, or 10 wt.% or less, based on a total weight of polymerizable components.

[0065] Second Nitrogen-Containing Monomer

[0066] Polymerizable compositions according to the present disclosure include a second nitrogencontaining monomer that has a nitrogen atom directly attached to a vinyl group. The second nitrogencontaining monomer is a polymerizable component. Without wishing to be bound by theory, it is believed that the presence of the nitrogen atom next to the vinyl group decreases the speed of homopolymerization of the monomer, yet the monomer copolymerizes quickly with other acrylic components. Additionally, use of a nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group tends to increase the high temperature shear modulus and therefore shear resistance when copolymerized with acrylates (at a cost of high copolymerization exotherm / heat), whereas the first nitrogen-containing monomer tends to reduce high temperature shear modulus and shear resistance when copolymerized with acrylates.

[0067] Suitable examples of monomers that have a nitrogen atom directly attached to a vinyl group for use as the second nitrogen-containing monomer include for instance and without limitation, N-vinyl pyrrolidone, vinyl methyl oxazolidinone, or N-vinyl caprolactam, N-vinyl imidazole, N-vinyl carbazole, N-vinyl formamide, N-methyl-N-vinyl acetamide, N-vinyl piperidone, and combinations thereof.

[0068] The second nitrogen-containing monomer is present in an amount of 5 wt.% or greater, based on a total weight of polymerizable components, such as 6 wt.%. 7 wt.%. 8 wt.%. 9 wt.%, 10 wt.%, 11 wt.%.12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, or 20 wt.%, based on a total weight of polymerizable components; and 30 wt.% or less, based on a total weight of polymerizable components, 28 wt.%, 26 wt.%, 25 wt.%, 24 wt.%, 22 wt.%, 20 wt.%, 18 wt.%, 16 wt.%, 15 wt.%, 14 wt.%, 12 wt.%. or 10 wt.% or less, based on a total weight of polymerizable components.

[0069] In some cases, the combined amount of components b) (i.e., the first nitrogen-containing monomer) and c) (i.e., the second nitrogen-containing monomer) is 10 wt.% or greater, based on a total weight of polymerizable components, such as 12 wt.%. 14 wt.%, 15 wt.%, 16 wt.%, 18 wt.%, 20 wt.%, 22 wt.%. 24 wt.%, 25 wt.%, 26 wt.%, 28 wt.%, 30 wt.%, 32 wt.%, 34 wt.%, or 35 wt.% or greater, based on a total weight of polymerizable components; and 45 wt.% or less, based on a total weight of polymerizable components, such as 42 wt.%, 40 wt.%, 38 wt.%, 36 wt.%, 35 wt.%, 34 wt.%, 32 wt.%, 30 wt.%, 28 wt.%, 26 wt.%, 25 wt.%, 24 wt.%, 22 wt.%, or 20 wt.% or less, based on a total weight ofpolymerizable components. Stated another way, in some cases the combined amount of components b) and c) ranges from 10 wt.% to 45 wt.%. based on a total weight of polymerizable components.

[0070] In some embodiments, a weight ratio of component b) (i.e., the first nitrogen-containing monomer) to component c) (i.e., the second nitrogen-containing monomer) is 1 : 1 or greater, such as 2: 1, 3: 1, 4: 1. 5: 1, or 6: 1. Stated another way, in certain embodiments, a weight ratio of component b) to component c) is between 1 and 6. As such, the first nitrogen-containing monomer may be present in a larger amount than the second nitrogen-containing monomer, including a significantly larger amount.

[0071] Ionic Liquid

[0072] Polymerizable compositions according to the present disclosure include an ionic liquid. In some cases, an ionic liquid is a polymerizable component, whereas in other cases an ionic liquid is not a polymerizable component, depending on the specific ionic liquid.

[0073] The presence of an ionic liquid may be useful in easing the peeling (or peel-ability) of the adhesive when reworking or recycling an article. An ionic liquid is a unique salt, which is in a liquid state at about 100 °C or less, has negligible vapor pressure, and high thermal stability. The ionic liquid is composed of a cation and an anion and has a melting point of no more than 100 °C, (i.e., being a liquid at about 100 °C or less), about 95 °C or less, or even about 80 °C or less. Certain ionic liquids exist in a molten state even at ambient temperature since their melting points are less than room temperature, and therefore they are sometimes referred to as ambient temperature molten salts. The cation and / or anion of the ionic liquid are relatively sterically bulk}', and typically one and / or both of these ions are an organic ion. Optionally, the cation or anion of the polymerized ionic liquid is non-protonated. The ionic liquid can be synthesized by known methods, for example, by a process such as anion exchange or metathesis process, or via an acid-base or neutralization process.

[0074] The cation of the ionic liquid of the present disclosure may be a nitrogen-containing cation (e.g., an ammonium ion), a phosphonium ion, a sulfonium ion, an imidazolium ion, a pyridinium ion, an iodonium ion, or the like, including various delocalized heteroaromatic cations, but is not limited thereto. The nitrogen-containing cation includes ions such as, alkylammonium, imidazolium, pyridinium, pyrrolidinium, pyrrolinium, pyrazinium, pyrimidinium, triazonium, triazinium, quinolinium, isoquinolinium. indolinium. quinoxalinium, piperidinium. oxazolinium, thiazolinium, morpholinium, or piperazinium. Examples of the phosphonium ion include tetraalkylphosphonium, arylphosphonium, or alkylarylphosphonium. Examples of the sulfonium ion include alkylsulfonium, arylsulfonium, thiophenium. or tetrahydrothiophenium. The alkyl group directly bonded to a nitrogen atom, a phosphorus atom, or a sulfur atom may be a linear, branched or cyclic alkyl group having a carbon number of at least 1, 2, or even 4 and not more than 8, 10, 12. 15, or even 20. The alkyl group may optionally contain heteroatoms such as O, N, and / or S in the chain or at the end of the chain (e.g.. a terminal -OH group). The aryl group directly bonded to a nitrogen atom, a phosphorus atom, or a sulfur atom may be a monocyclic or condensed cyclic aryl group having at least 5, 6, or even 8 carbon atoms and not more than 12, 15, or even 20 carbon atoms. An arbitrary site in the structure constituting such a cation may be further substituted by an alky l group, an alkenyl group, an alkynyl group, a cycloalkylgroup, an aryl group, an aralkyl group, an arylalkyl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carbonyl group, a carboxyl group, an ester group, an acyl group, an amino group, a dialkylamino group, an amide group, an imino group, an imide group, a nitro group, a nitrile group, a sulfide group, a sulfoxide group, a sulfone group, a halogen atom or the like. A heteroatom such as oxygen atom, nitrogen atom, sulfur atom, and / or silicon atom may be contained in the main chain or ring of the structure constituting the cation.

[0075] Specific examples of the cation include N-ethyl-N'-methylimidazolium, N-methyl-N'-butylimidazolium, N-methyl-N-propylpiperidinium, N,N,N-trimethyl-N-propylammonium, N-methyl-N. N, N -tripropylammonium, N, N, N -trimethy 1-N -buty lammoniuim, N. N. N -trimethy 1-N -methoxy ethylammonium. N-methyl-N, N, N-tris(methoxyethyl)ammonium, N, N-dimethyl-N-butyl-N-methoxy ethylammonium, N, N-dimethy l-N. N-dibut lammonium, N-methyl-N, N-dibutyl-N-methoxy ethylammonium, N-methyl-N, N, N-tributy lammonium. N, N, N-trimethyl-N -hexylammonium, N, N-diethyl-N-methyl-N-(2-inethoxyethy l)ammonium, 1 -propyl-tetrahydrothiophenium, 1-butyl-tetrahydrothiophenium, 1-pentyl-tetrahydrothiophenium, 1-hexyl-tetrahydrothiophenium, glycidyltrimethylammonium, N-ethylacryloyl-N,N,N-trimethylammonium, N-ethyl-N-methylmorpholinium, N,N,N-trioctylammonium, N-methyl-N,N,N-trioctylammonium, N,N-dimethyl-N-octyl-N-(2-hydroxyethyl)ammonium, triethylsulfonium, or mixtures thereof.

[0076] The anion of the ionic liquid of the present disclosure may be, for example, a sulfate (R-OSCty); a sulfonate (R-SO3); a carboxylate (R-CO2 ); a phosphate ((RO)2P(=O)O); a borate represented by the formula: BR’, such as tetrafluoroborate (BF4 ), tetraalkylborate, and tetraphenylborate; an oxalato borate, such as lithium difluoro(oxalato)borate; a phosphate represented by the formula: PR,. such as (PFe ) and hexaalkylphosphate; an imide (R2N ); a sulfonylimide; a sulfidoimide; an imide: a methide (R3C); a nitrate ion (NO3); a nitrite ion (NO2 ); a dicyanamide ((CNfiN’); a tricyanomethanide; or a halide such as iodide. In the formulas listed above, each R may be independently a hydrogen atom, a halogen atom (fluorine, chlorine, bromine, iodine), a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, arylalkyl, acyl or sulfonyl group, or the like. A heteroatom such as an oxygen atom, a nitrogen atom or a sulfur atom may be contained in the main chain or ring of the group R. and a part or all of hydrogen atoms on the carbon atom of the group R may be replaced with fluorine atoms. In the case where a plurality of R's are present in the anion, these R's may be the same or different.

[0077] In select cases, the anion of a polymerizable ionic liquid is a carboxylate, e g., a deprotonated acrylic acid-type monomer having a coordinating cation that is free of a protonated nitrogen. One such example cation is l-methyl-3-octylimidazolium.

[0078] In some embodiments, it is advantageous to use a perfluorinated ion, such as a perfluorinated anion to achieve excellent corrosion resistance and electro-debonding. However, the use of fluorinated ions should be balanced with the environmental impact of the finished good, as some fluorinated chemicals may have restricted use due to environmental concerns. Examples of an anion containing a perfluoroalkyl group, which can be used, include a bis(perfluoroalkylsulfonyl)imide ((RfSO₂)₂N⁻), a perfluoroalkylsulfonate (RfSO₃⁻) and a tris(perfluoroalkylsulfonyl)methide ((RfSO₂)₃C⁻) (wherein Rfrepresents a perfluoroalkyl group). The perfluoroalkyl group may comprise, for example, from at least 1.2. 3 or even 4 to at most 8, 10, 12, 15. or even 20 carbon atoms. Specific examples of the bis(perfluoroalkylsulfonyl)imide include: bis(trifluoromethanesulfonyl)imide, bis(pentafluoroethanesulfonyl)imide, bis(heptafluoropropanesulfonyl)imide. or bis(nonafluorobutanesulfonyl)imide. Specific examples of the perfluoroalkylsulfonate include: trifluoromethanesulfonate, pentafluoroethanesulfonate, heptafluoropropanesulfonate, or nonafluorobutanesulfonate. Specific examples of the tris(perfluoroalkylsulfonyl)methide include: tris(trifluoromethanesulfonyl)methide. tris(pentafluoroethanesulfonyl)methide, tris(heptafluoropropanesulfonyl)methide, or tris(nonafluorobutanesulfonyl)methide. Examples of fluorinated anions not comprising a C-F bond are hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, difluoroiodide, and bis(fluorosulfonyl)imide.

[0079] In one or more embodiments, the polymerizable anion has a sulfonate group and has a structure such as, for example:

[0080] In one or more embodiments, the polymerizable anion can be combined with non-polymerizable cations, including but not limited to structures such as, for example:

[0081] imidazolium cations having the structure:

[0082] phosphonium cations having the structure:R3 Fl+lj’-R2R4

[0083] pyridinium cations having the structure:Ri

[0084] ammonium cations having the structure:R Ri+N-R2R4

[0085] of sulfonium cations having the structure:+1R3+S~R2or heterocycles thereof.

[0086] Suitable R groups (e.g., R, R1, R2, R3, and R4) may independently be selected from an alkyl moiety, an alicyclic moiety, an aryl moiety, an alkalicyclic moiety, an alkaryl moiety, an alicyclicalkyl moiety, and an aralicyclic moiety, wherein such moiety may comprise one or more oxygen atoms, nitrogen atoms, or other functional groups.

[0087] As for the ionic liquid composed of the above-described cation and anion. N-butyl-N'-methylimidazolium bis(trifluoromethanesulfonyl)imide, tri-ethyl sulfonium bis(trifluoromethanesulfonyl)imide. N-butyl- N'-methylimidazolium hexafluorophosphate, N-butyl- N'-methylimidazolium iodide, ethyl pyridinium bis(trifluoromethanesulfonyl)imide, trimethyl ammonium ethyl acrylate bis(trifluoromethanesulfonyl)imide, N-butyl- N'-methylimidazolium dicyanamide, N-ethyl-N'-methylimidazolium dicyanamide, and / or a tetra alkyl ammonium with hydroxy functionality with bis(trifluoromethanesulfonyl)imide counterion, available under the trade designation " FC-5000" from 3M Co., Maplewood. MN can be advantageously used as the ionic liquid, because of their excellent removability during electro-debonding due to reduced bond strength upon application of electricity.

[0088] Enough ionic liquid should be added to enable electro-debonding, while too much ionic liquid may negatively impact the physical properties of the adhesive, such as shear, peel adhesion, and / or ability to survive the random free fall test. The type of ionic liquid used may impact how much can be added without negatively impacting the physical properties of the adhesive. For example, if the ionic liquid can be polymerized into (meth)acry late matrix, for example, the ionic liquid comprises at least one (or even at least two) acrylate, methacrylate, or styrene functional group or combinations thereof, more ionic liquid may be incorporated into the adhesive. It is noted that use of an ionic liquid that contains at least two functional groups may be less preferable for applications in which there is a substantial delay between polymerization and final use of the adhesive because the presence of multiple functional groups could result in disadvantageous early gelation of the adhesive.

[0089] Exemplary suitable polymerizable ionic liquids include for instance and without limitation. N, N, N-trimethyl ammonium etliyl acrylate bis(fluorosulfonyl)imide, N, N, N-trimethyl ammonium ethyl acrylate iodide, N, N, N-trimethyl ammonium ethyl acrylamide bis(fluorosulfonyl)imide, N, N, N-trimethyl ammonium ethyl acrylate bis(trifluoromethane sulfonyl)imide, N-hexyl-N, N-dimethyl ammonium ethylacrylate bis(fluorosulfonyl)imide. N-hexyl-N, N-dimethyl-ammonium ethyl acrylamide tricyanomethanide or N, N, N-trimethyl ammonium ethyl acrylate tricyanomethanide. N-butyl-imidazolium-N'-ethyl acrylate bis(fluorosulfonyl)imide, N-butyl-imidazolium-N'-ethyl acrylate tricyanomethanide, dibutyl-sulfonium-ethyl acrylate bis(fluorosulfonyl)imide, dibutyl-phosphonium ethyl acrylate bis(fluorosulfonyl)imide, 3-sulfopropyl acrylate N-octyl-N-methyl-imidazolium or 3-sulfopropyl acrylate N-butyl-N-methyl-imidazolium. N-vinyl-imidazolium bis(fluorosulfonyl)imide, sulfopropyl acrylamide N-butyl-N'-methyl imidazolium. sulfopropyl acrylamide N-octyl-N'-methyl imidazolium. styrene sulfonate N-butyl-N'-methyl imidazolium, styrene sulfonate N-octyl-N'-methyl imidazolium.

[0090] As noted above, the ionic liquid may comprise functionality of the first nitrogen-containing monomer to provide both component b) and component d) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component c) and component d). For instance, sulfopropyl acrylamide N-butyl-N'-methyl imidazolium is an ionic liquid that includes acry lamide functionality’ and satisfies the provision of both components b) and d). Likewise, N-vinyl-imidazolium bis(fluorosulfonyl)imide is an ionic liquid that includes functionality in which a nitrogen atom is directly attached to a vinyl group and satisfies the provision of both components c) and d). In some embodiments, a polymerizable composition includes an ionic liquid that provides both components b) and d). In some embodiments, a polymerizable composition includes an ionic liquid that provides both components c) and d). In some embodiments, a polymerizable composition includes a first ionic liquid that provides both components b) and d) and a second ionic liquid that provides both components c) and d). As these ionic liquids include nitrogen-containing monomer functionality, they can alternatively be referred to as nitrogen-containing monomers.

[0091] A polymerizable ionic liquid that may be present in an amount of 1 wt.% or greater, based on a total weight of polymerizable components, such as 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 18 wt.%, or 20 wt.% or greater, based on a total weight of polymerizable components; and 30 wt.% or less, based on a total weight of polymerizable components, such as 28 wt.%, 26 wt.%, 24 wt.%, 22 wt.%, 20 wt.%, 18 wt.%, 16 wt.%, 15 wt.%, 14 wt.%, 12 wt.%, or 10 wt.% or less, based on a total weight of polymerizable components.

[0092] If the ionic liquid is not polymerizable into the (meth)acrylate matrix of the adhesive, less ionic liquid should be used due to it negatively impacting the physical properties of the adhesive (such as static shear performance). In embodiments in which the ionic liquid comprises a non-polymerizable ionic liquid, the ionic liquid may be present in an amount of 2 parts per hundred parts resin (phr) or greater. 3 phr, 4 phr, 5 phr, 6 phr, 7 phr. 8 phr. 9 phr. or 10 phr or greater; and 20 phr or less, 18 phr, 16 phr, 14 phr, 12 phr, 10 phr, 8 phr, or 6 phr or less.

[0093] The choice of the ionic liquid used in the adhesive can impact electro-debonding. For example, it may be advantageous to choose ionic liquids that have a high conductivity or ionic mobility. While not being limited by theory, it is believed that increased ionic liquid mobility in the adhesive is beneficial for electro-debonding. As such, it may be beneficial for the ionic liquid to be highly soluble in the adhesivematrix (i.e., the ionic liquid does not phase separate from the adhesive matrix). High mobility and high conductivity (e.g., having sheet resistance less than 1x103ohms per square) of the ionic liquid in the adhesive matrix could help enable electro-debonding in thicker adhesives. In some embodiments the adhesive thickness could be 10, 25, 50, 60, 70, 80, 90, 100, 150. 200, 250, 300. 400, or even up to 500 microns thick. Alternatively, or additionally, it may be advantageous to choose ionic liquids that have electrochemically unstable cations or anions. While not wanting to be limited by theory, it is believed that more electrochemically unstable cations or anions could produce an increased electro-debonding response. As such, it may be beneficial to choose cations comprised of imidazolium or pyridinium derivatives over quaternary ammonium derivatives.

[0094] In one embodiment, it may be beneficial for environmental reasons to choose ionic liquids that do not contain carbon-fluorine bonds. As such, it may be beneficial to choose ionic liquids containing inorganic fluorine such as the hexafluorophosphate or tetrafluoroborate ion in lieu of organic fluorine such as bis(trifluoromethylsulfonyl)imide.

[0095] Crosslinker

[0096] Polymerizable compositions according to the present disclosure optionally include a crosslinker. The crosslinker is a polymerizable component.

[0097] Nonlimiting examples of suitable crosslinkers include multifunctional (meth)acrylate(s), e.g.. butanediol diacrylate or hexanediol diacrylate, or other multifunctional crosslinkers such as divinylbenzene and mixtures thereof. In some embodiments, at least 0.005, 0.01, 0.02, 0.05, or even 0.08 wt.% of the crosslinker is used based on the total weight of polymerizable components. In some embodiments, at most 0.1, 0.2, 0.5, 1, 2. or even 5 wt.% of the crosslinker is used based on the total weight of polymerizable components.

[0098] Ethoxy Group-containing (Meth) acrylate Monomer

[0099] Polymerizable compositions according to the present disclosure optionally include an ethoxy group-containing (meth)acrylate monomer. The ethoxy group-containing (meth)acrylate monomer is a polymerizable component.

[0100] Exemplary suitable include for instance and without limitation, 2-ethoxy ethyl (meth)acrylate, 2-methoxy ethyl acrylate. 2-(2-ethoxyethoxy)ethyl acrylate, and 2- [2-(2 -methoxy ethoxy)ethoxy]. When included in a polymerizable composition, an ethyl acry late ethoxy group-containing (meth)acrylate monomer may be present in an amount of 5 wt.% or greater, based on a total weight of polymerizable components, such as 5 wt.%, 10 wt.%, 15 wt.%, 20 wt.%, 25 wt.%, 30 wt.%, 35 wt.% or greater, based on a total weight of polymerizable components; and 50 wt.% or less, based on a total weight of polymerizable components, such as 45 wt.%, 40 wt.%, 35 wt.%, 30 wt.%, 25 wt.%, 20 wt.%, 15 wt.%, or 10 wt.% or less, based on a total weight of polymerizable components.

[0101] A dditive

[0102] Polymerizable compositions according to the present disclosure optionally include at least one additive. Typically, each additive that is included may be present (independently) in an amount of 1 phror greater. 2 phr, 3 phr. 5 phr. 7 phr, or 10 phr or greater; and 20 phr or less. 18 phr, 16 phr, 15 phr. 14 phr. 12 phr, 10 phr, or 8 phr or less.

[0103] In certain embodiments, at least one additive is selected from the group consisting of an adhesion promoter (e.g., glycidyl propyl trimethoxy silane), a stabilization agent (e.g.. calcium carbonate), a corrosion inhibitor (e.g., benzotriazole or 2-(methacryloyloxy)ethyl acetoacetate), a conducting salt (e.g., lithium bis(fluorosulfonyl)imide or sodium hexafluorophosphate), and a polymer having a glass transition temperature of at least 40 degrees Celsius (e.g., polyvinyl butyral). Except for certain polymers, the additives are not polymerizable components.

[0104] Filler

[0105] Polymerizable compositions according to the present disclosure optionally include at least one filler. The fillers are not polymerizable components.

[0106] In certain embodiments, a filler comprises a plurality of hollow glass microspheres, a plurality of polymeric microparticles, a plurality of polymeric nanoparticles each comprising an interior region comprising a polymer having a glass transition temperature below room temperature and an outer shell comprising a polymer having a glass transition temperature of at least 50°C, an organo-phosphinate, a plurality of alumina particles, a plurality of pre-expanded hollow polymeric microspheres, a plurality of conductive particles (e.g., nickel coated graphite or carbon black), or combinations thereof.

[0107] Suitable hollow microspheres include for instance and without limitation, hollow glass microspheres. Hollow glass microspheres can be made by techniques known in the art (see, e.g., U. S. Pat. Nos. 2,978,340 (Veatch et al.); 3,030.215 (Veatch et al.); 3,129,086 (Veatch et al.); and 3,230,064 (Veatch et al.); 3,365,315 (Beck et al.); 4,391,646 (Howell); and 4,767,726 (Marshall); and U. S. Pat. App. Pub. No. 2006 / 0122049 (Marshall et. al).

[0108] Exemplary polymeric microparticles include for instance, the polymeric microspheres described in detail in PCT Publication No. WO 2023 / 175424 (Maher et al.). Exemplary suitable polymeric nanoparticles include, for instance, the polymeric nanoparticles described in detail in PCT Publication No. WO 2023 / 228050 (Moughton et al.).

[0109] Suitable organo-phosphinate fillers include for instance and without limitation, those commercially available under the trade designations “EXOLIT OP 930”. “EXOLIT OP 935”. and “EXOLIT OP 1230”, all from Clariant Ltd (Louisville, KY), which are each white, fine-grained powders of aluminum diethyl phosphinate flame retardant particles. Advantageously, the use of organo-phosphinate fillers tends to improve drop resistance of an adhesive even in the absence of other additives that have also been used to increase shear modulus.

[0110] Expanded microspheres are obtained by exposing expandable microspheres to heat. A wide range of expandable microspheres are suitable. Suitable expandable microspheres are ones with low density, high elasticity, and low moisture absorption such as those commercially available from Nouryon under the trade name “EXPANCEL” such as “EXPANCEL 920DU20”. In some embodiments, the expandable microspheres have a maximum expansion ratio of 6.4.

[0111] Exemplary conductive particles include for instance and without limitation, carbon particles (e.g., carbon black) or metal particles of silver, copper, nickel, gold, tin, zinc, platinum, palladium, iron, tungsten, molybdenum, alloys thereof, solder, or the like, or particles prepared with a surface covering or coating of a conductive coating of a metal, alloy, or the like, can be used. It also is possible to use non-conductive particles of a polymer such as polyethylene, polystyrene, phenol resin, epoxy resin, acryl resin or benzo guanamine resin, or glass beads, silica, graphite or a ceramic, with conductive surface coatings (e.g., coating(s) of metal(s). alloy(s), or the like), e.g., nickel coated graphite particles.

[0112] Useful electrically conductive particles are available in a variety of shapes (e.g., spherical, ellipsoidal, cylindrical, flakes, needle, whisker, platelet, agglomerate, crystal, acicular). The particle may have a slightly rough or spiked surface. The shape of the electrically conductive particles is not particularly limited but a nearly spherical shape is preferred in some embodiments. The choice of shape is typically dependent upon the rheology of the selected resin components and ease of processing of the final resin / particle mix. Combmations of particle shapes, sizes, and hardness may be used in the disclosed adhesive compositions.

[0113] Carboxylic Acid-containing (Meth) acrylate Monomer

[0114] Polymerizable compositions according to the present disclosure optionally include a carboxylic acid-containing (meth)acrylate monomer. The carbox lic acid-containing (meth)acrylate monomer is a polymerizable component. Exemplary suitable carboxylic acid-containing (meth)acrylate monomers include for instance and without limitation, acrylic acid, methacrylic acid, and carboxyethyl b-acrylate.

[0115] It has surprisingly been discovered that while a very small amount of carboxylic acid-containing ('mcth)acry late monomer, namely an amount of less than 2 phr of the polymerizable composition may be used, including even 2 phr, has a significantly negative impact on the ability to electro-debond an adhesive when measured using a tensile pushout test.

[0116] (Meth) aery late Macromer

[0117] Polymerizable compositions according to the present disclosure optionally include a (meth)acrylate macromer. The (meth)acrylate macromer is a polymerizable component. Typically, the addition of the (meth)acrylate macromer is thought to decrease the shear storage modulus and Tgof the resulting composition, enabling the resulting adhesive to have improved resistance to tensile debonding as demonstrated by improved performance in random free fall testing.

[0118] The (meth)acrylate macromer typically has a (meth)acryloyloxy group plus (i) a poly(ethylene oxide) group, (ii) poly(propylene oxide) group, (iii) polyethylene oxide-co-propylene oxide) group, which can also be referred to as a polyethylene glycol), polypropylene glycol), or poly(ethylene glycol-co-propylene glycol) groups respectively, (iv) a poly(tetrahydrofuran) group, or (v) combinations thereof. If the macromer contains a poly(ethylene oxide) group, it can be referred to as a poly(ethylene oxide) (meth)acrylate. If the macromer contains a polypropylene oxide) group, it can be referred to as a polypropylene oxide) (meth)acrylate. If the macromer contains a polyethylene oxide-co-propylene oxide) group, it can be referred to as a polyethylene oxide-co-propylene oxide) (meth)acrylate, which isa copolymer. If the macromer contains a poly(tetrahydrofuran) group, it can be referred to as a poly (tetrahydrofuran) (meth)acry late.

[0119] The (meth)acrylate macromer typically has a number average molecular weight in a range of 300 to 10,000 Daltons. For example, the (meth)acrylate macromer has a number average molecular weight no greater than 10.000, 8000. 6000. 4000. 2000. 1000. 800, 650, or even 500 Daltons. The number average can be determined by gel permeation chromatography using techniques known in the art.

[0120] The (meth)acrylate macromer often has a Tg(as measured using a homopolymer of the macromer) that is no greater than -10 °C. For example, the glass transition temperature can be no greater than -10. -20, -30, or even -40 °C. In one embodiment, the Tgis less than -70 or even -80 °C. Such a low macromer Tgimparts compliance and flexibility to the (meth)acrylate copolymer and to the adhesive composition.

[0121] Examples of such commercially available (meth)acrylate macromers include polyethylene glycol) methyl ether aery late, such as that having a reported number average molecular weight (Mn) of 480 Daltons (available from Sigma-Aldrich) and poly (propylene glycol) acrylate, such as that having a reported number average molecular weight of 475 Daltons (available from Sigma- Aldrich). Other suitable macromers are available under the trade designation BISOMER from Geo Specialty Chemicals, Ambler, PA, such as BISOMER PPA6 (polypropylene glycol) acry late reported to have a number average molecular weight of 420 Daltons), BISOMER PEM63P HD (a mixture of poly (ethylene glycol) methacrylate and polypropylene glycol) reported to have a number average molecular weight of 524 Daltons), BISOMER PPM5 LI polypropylene glycol) methacrylate reported to have a number average molecular weight of 376 Daltons), BISOMER PEM6 LD (poly (ethylene glycol) methacrylate reported to have a number average molecular weight of 350 Daltons), BISOMER MPEG350MA (methoxy polyethylene glycol) methacrylate) reported to have a number average molecular weight of 430 Daltons), and BISOMER MPEG550MA (methoxy polyethylene glycol) methacrylate reported to have a number average molecular weight of 628 Daltons). Other suitable macromers are available under the trade designation MIRAMER from Miwon Specialty Chemical Company, Gyeonggi-do, Korea, such as MIRAMER M193 MPEG600MA (methoxy poly(ethylene glycol) methacrylate reported to have a number average molecular weight of 668 Daltons), MIRAMER M164 (nonyl phenol poly(ethylene glycol) acrylate reported to have a number average molecular weight of 450 Daltons), MIRAMER M1602 (nonyl phenol poly(ethylene glycol) acrylate reported to have a number average molecular weight of 390 Daltons), and MIRAMER M166 (nonyl phenol poly(ethylene glycol) acrylate reported to have a number average molecular weight of 626 Daltons. Still other suitable macromers are available from San Esters Corporation, New York, NY such as MPEG-A400 (methoxy polyethylene glycol) acrylate reported to have a number average molecular weight of 400 Daltons), and MPEG-A550 (methoxy poly(ethylene glycol) acrylate reported to have a number average molecular weight of 550 Daltons. Examples of commercially available polyester macromers include the PLACCEL F SERIES from Daicel Corporation Osaka Japan, which are epsilon-caprolactone-modified hydroxyalkyl(meth)acrylates. i.e., FM2D reported to have a molecular weight of 358 Daltons, FA2D reported to have a molecular weight of 344 Daltons, orFA10L reported to have a molecular weight of 1256 Daltons. Other such commercial sources include polyester macromers from BASF, such as hydroxy ethyl caprolactone acrylate, or HECLA, which is reported to have a molecular weight of 436 Daltons. Various combinations of such macromers may be used if desired.

[0122] The macromer having the poly(tetrahydrofuran) group can be prepared, for example, by polymerizing tetrahydrofuran using cationic polymerization. For instance, such a polymerization is described in detail in PCT Application Publication No. WO 2023 / 175421 (Maher et al.), incorporated herein by reference in its entirety. The weight average molecular weight of the poly (tetrahydrofuran) (meth)acrylate macromer is typically in a range of 300 to 10,000 Daltons, which can be determined using known methods such as gel permeation chromatography with polystyrene standards. If the molecular weight is higher, it may not be miscible with the other components in the polymerizable composition and / or it may crystallize before, during, or after polymerization of the matrix. In many embodiments, the poly(tetrahydrofuran) (meth)acrylate macromer has a weight average molecular weight of at least 500, 600, 800, 1,000, 2,000 or even 3,000 Daltons and up to 10,000, 8,000, 6,000, 5,000, or even 3,000 Daltons.

[0123] In some embodiments, the (meth)acrylate macromers include one or more of the following: a polyethylene oxide) group, a polypropylene oxide) group, a poly(ethylene oxide-co-propylene oxide group, a poly(tetrahydrofuran) group; or a poly(ester) group or combinations thereof.

[0124] Initiators

[0125] An initiator is preferably added to aid in polymerization of the polymerizable composition. The type of initiator used depends on the polymerization process. In a preferred embodiment, photoinitiators are used to initiate the polymerization. Useful photoinitiators include benzoin ethers such as benzoin methyl ether or benzoin isopropyl ether, substituted benzoin ethers such as 2-methyl-2-hydroxy propiophenone, or photoactive oxides such as 1 -phenyl- 1, 2-propanedione-2-(o-ethoxycarbonyl)oxime. An example of a commercially available photoinitiator is " IRGACURE 651” available from Ciba, having a formula of 2,2-dimethoxy-1,2-diphenylethane-1-one. Generally, the photoinitiator is present in an amount of about 0.01 phr to 0.10 phr. The polymerization may be carried out in the presence of at least one free-radical initiator. Useful free-radical UV initiators include, for example, benzophenones. In another embodiment, a thermal initiator may be used, such as for example. AIBN (azobisisobutyronitrile) and / or peroxides.

[0126] At Least Partially Polymerized Reaction Product of Polymerizable Compositions

[0127] In a second aspect, an at least partially polymerized reaction product of the polymerizable composition is provided. The polymerizable composition is according to any embodiment of the first aspect described in detail above.

[0128] The polymerizable composition may be at least partially polymerized by techniques known in the art, including, for example, the conventional techniques of solventless polymerization. A “substantially solvent free” polymerization refers to less than 5%, 2%, 1% or even 0.5% by weight of solvent being used, based on the weight of the polymerizable components, and more preferably no additional solvent isadded during the polymerization. The term "solvent” refers both to water and to conventional organic solvents used in the industry which are volatilized in the process.

[0129] As noted above, the polymerizable composition optionally includes an initiator for photoinitiation or thermal initiation of polymerization of polymerizable components of the polymerizable composition. By only partially polymerizing the composition, the partially polymerized reaction product may be easier to handle during use in an adhesive application.

[0130] Pressure Sensitive Adhesive Articles

[0131] In a third aspect, a pressure sensitive adhesive article is provided. The pressure sensitive adhesive article comprises an adhesive composition comprising the at least partially polymerized reaction product according to the second aspect, wherein the adhesive composition is disposed on at least a portion of a substrate.

[0132] In certain embodiments, adhesive compositions disclosed herein comprising an ionic liquid can undergo electrically induced adhesive debonding, wherein the adhesive composition can be debonded on demand with the application of a voltage across adherend substrates. Although not wanting to be limited by theory, it is believed that when a voltage is applied to the adhesive composition comprising an ionic liquid, electrolysis of the ionic liquid occurs, wherein the cations migrate toward the cathode side and the anions migrate toward the anode side, thereby weakening the adhesive interface.

[0133] Advantageously, in at least certain embodiments according to the present disclosure, an adhesive composition exhibits a tensile pushout strength of greater than 0.2 megaPascals (MPa), as determined by the Tensile Pushout Test Method. The Tensile Pushout Test Method is described in detail in the Examples below. In some cases, an adhesive composition exhibits a tensile pushout strength of greater than 0.3 MPa, 0.4 MPa, 0.5 MPa, 0.6 MPa, 0.7 MPa. 0.8 MPa, 0.9 MPa, 1.0 MPa. 1.1 MPa, 1.2 MPa. 1.3 MPa, 1.4 MPa, 1.5 MPa, 1.6 MPa, 1.7 MPa. 1.8 MPa, 1.9 MPa, or even greater than 2.0. MPa. as determined by the Tensile Pushout Test Method.

[0134] In at least certain embodiments according to the present disclosure, an adhesive composition exhibits a decrease in tensile pushout strength of at least 50% following subjection to 9 volts (V), 10 V, 20 V, 30 V, 40 V. or 50 V for one minute, as determined by the Tensile Pushout Test Method. In some cases, an adhesive composition exhibits a decrease in tensile pushout strength of at least 55%. 60%. 65%, 70%, 75%. 80%, 85%, 90%, or at least 95%. as determined by the Tensile Pushout Test Method. The decrease in tensile pushout strength following subjection to the voltage is a measure of the extent of electro-debonding capability of an adhesive composition, with a larger decrease indicating greater debonding.

[0135] In at least certain embodiments according to the present disclosure, an adhesive composition exhibits a decrease in peel strength of at least 50% following subjection to 50 volts (V) for one minute or following subjection to 10 V for 5 seconds, 10 seconds, 20 seconds. 30 seconds, 45 seconds, or 60 seconds, as determined by the Peel Adhesion Test Method. In some cases, an adhesive composition exhibits a decrease in peel strength of at least 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or at least95%, as determined by the Peel Adhesion Test Method. The decrease in peel strength following subjection to the voltage is a measure of the extent of electro-debonding capability of an adhesive composition, with a larger decrease indicating greater debonding.

[0136] It is noted that when trying to electrically debond compositions comprising acrylic acid and ionic liquids, it was surprisingly found that the electrically debonded adhesion strength returned within 60 seconds after voltage application. In contrast, compositions that lacked acrylic acid and contained either no polar monomers or only non-acidic polar monomers, did not exhibit increased adhesion strength within 60 seconds after voltage application. When the adhesive compositions are used within one exemplary intended application to rapidly remove adhered parts for re-work or part recycling, it would be highly desirable to maintain a lower adhesion strength over the course of at least several minutes to ensure rapid and facile removal of adhered components. This is surprisingly achieved with acid free compositions which maintain a loss in adhesion strength.

[0137] Referring to FIG. 1 A, a pressure sensitive adhesive article 100a comprises a substrate 110 having a first major surface 112 and a layer of an adhesive composition 120 disposed on at least a portion of the first major surface 112 of the substrate 110. A second major surface 114 of the substrate 110 is also indicated in FIG. 1 A. In some embodiments, the substrate is one of the following: a liner comprising a release agent, a backing, or a carrier.

[0138] Referring to FIG. IB, a pressure sensitive adhesive article 100b comprises a substrate 110 having a first major surface 112 and a layer of an adhesive composition 120 disposed on at least a portion of the first major surface 112 of the substrate 110. The pressure sensitive adhesive article 100b further comprises an optional second adhesive layer 130 disposed on at least a portion of the second major surface 114 of the substrate 110. In such an embodiment, the substrate 110 is a carrier and the substrate 110 is disposed between the adhesive composition 120 and the second adhesive layer 130.

[0139] In some embodiments, the at least partially polymerized reaction product comprises a polymer that is a polymerized reaction product of at least components a), b), and c). This polymer may not get incorporated into a crosslinked network of the pressure sensitive adhesive article.

[0140] Liners

[0141] Suitable (e.g.. release) liners may comprise flexible paper and polymeric films having sufficient dimensional stability to hold layers formed thereon in position without excessive stretching. Suitable paper liners include, but are not limited to. densified Kraft paper (commercially available from, for example. Loparex North America. Willowbrook. IL), poly -coated paper such as polyethylene coated Kraft paper, and the like. Suitable polymeric film / liners include, but are not limited to. thermoplastic polymer films including polyalkylenes, e.g., polyethylene and polypropylene; polybutadiene, polyisoprene; polyalkylene oxides, e.g., polyethylene oxide; polyesters, e.g.. PET and PBT; polyamides; polycarbonates, polystyrenes, block copolymers of any of the preceding polymers, and combinations thereof. Other suitable polymeric materials include polyimide, polysilicone, polytetrafluoroethylene, polyethylenephthalate, polyvinylchloride, or combinations thereof. Polymer blends of any of the above may also be employed, and nonwoven or woven liners may also be used.

[0142] In some embodiments, any or all of the major surfaces of a release liner may include a release coating, which may be the same or different, to tune or otherwise modify their release values. In various embodiments, which are not intended to be limiting, the release coatings applied to the major surfaces of the release liners may be selected from a fluorine-containing material, a silicone-containing material, a fluoropolymer, a silicone polymer, or a poly(meth)acrylate ester derived from a monomer including an alkyl (meth)acrylate having an alkyl group with 12 to 30 carbon atoms. In one embodiment, the alkyl group on the alkyl (meth)acrylate can be branched. Illustrative examples of useful fluoropolymers and silicone polymers can be found in U. S. Patent No. 4,472,480 (Olson), U. S. Patent No. 4,567,073 and U. S. Patent No. 4.614,667 (both Larson et al), incorporated herein by reference in their entireties. Illustrative examples of useful poly(meth)acrylate esters can be found in U. S. Patent Appl. Publ. No. 2005 / 0118352 (Suwa), incorporated herein by reference in its entirety.

[0143] Carriers

[0144] In one embodiment, an adhesive composition may be easily coated upon a carrier film to produce adhesive coated sheet materials cured via ultraviolet radiation or solvent coated or hot melt coated. Coating techniques known in the art may be used such as spray coating, flood coating, knife coating, Meyer bar coating, gravure coating, and double roll coating. The coating thickness will vary depending upon various factors such as, for example, the particular application or the coating formulation. Coating thicknesses of at least 5, 10, 20, 25, 30, 40, 50, 60, 75, or even 100 pm (micrometers) and at most 125, 150, 200, 250, 500, or even 1000 pm are contemplated. In some embodiments, having an adhesive layer with a thickness towards the higher end of the range may be preferable, for example, for better impact resistance performance.

[0145] The carrier film may be a flexible or inflexible backing material, a release liner, or a conductive carrier. Exemplary materials useful as the carrier film for the pressure sensitive adhesive articles of the disclosure include, but are not limited to, polyolefins such as polyethylene, polypropylene (including isotactic polypropylene and high impact polypropylene), polystyrene, polyester, including polyethylene terephthalate), polyvinyl chloride, poly(butylene terephthalate), poly(caprolactam), polyvinyl alcohol, polyurethane, poly(vinylidene fluoride), cellulose and cellulose derivatives, such as cellulose acetate and cellophane, and wovens and nonwovens. Commercially available carrier film include kraft paper (available from Monadnock Paper, Inc.); spun-bond poly(ethylene) and polypropylene), such as those available under the trade designations “TYVEK” and “TYPAR” (available from The Chemours Co.); and porous films obtained from poly(ethylene) and polypropylene), such as those available under the trade designations “TESLIN” (available from PPG Industries, Inc.), and " CELLGUARD" (available from Hoechst-Celanese). Exemplary’ conductive materials include for instance and without limitation, a layer of (e.g., metal) foil, a metal-coated polymeric film, a layer of a conductive primer coated onto or transferred onto the adhesive, a conductive primer deposited on a carrier layer, a conductive woven fabric, a conductive nonwoven fabric, a conductive mesh fabric (metal-coated insulative fibers), a conductive foam, a conductive elastomer, a conductive polymer film (e.g., poly(3,4-ethylenedioxythiophene), PEDOT) or coating on another film or polymer layer, and a conductiveceramic / alloy and / or oxides (e.g.. Indium Tin Oxide. ITO) with or without a carrier layer. In certain embodiments, the conductive material comprises a carbon-based material, e.g., conductive carbon black, carbon nanotubes, carbon fibers, carbon nanofibers, carbon nanotubes, graphite, and / or graphene.

[0146] The carrier film delivers the adhesive of the present disclosure to the desired substrate. The carrier film may comprise on the surface opposite the adhesive, a pigment, indicia, text, design, etc., which is then fixedly attached to the surface of the substrate or the carrier film may be free of such pigments and / or markings.

[0147] The thickness of an adhesive layer is typically at least 10. 15, 20, or even 25 microns (1 mil) and at most 50. 60, 70, 80, 90, 100, or even 400 microns (16 mils) thickness. In some embodiments, the thickness of an adhesive layer is no thicker than 100, 150, or even 200 microns and at most 300, 500, 1000, 1500, or even 2000 microns (80 mils) thick. The adhesive can be coated in single or multiple layers.

[0148] Backings

[0149] Adhesive compositions disclosed herein may advantageously be used to prepare a wide range of adhesive tapes and articles. Many of these tapes and articles contain backings or release liners used to support the layer of adhesive. As used herein a backing is a permanent support intended for final use of the adhesive article. A liner, on the other hand, is a temporary support that is not intended for final use of the adhesive article and is used during the manufacture or storage to support and / or protect the adhesive article. A liner is removed from the adhesive article prior to final use. To facilitate easy removal from the adhesive layer, the liner is typically coated with a release coating comprising a release agent. Such release agents are known in the art and are described, for example in " Handbook of Pressure Sensitive Adhesive Technology." D. Satas. editor, Van Nostrand Reinhold, New York, N. Y., 1989, pp. 585-600. In one embodiment, the release agent migrates to the surface (on the liner or release coating) to provide the appropriate release properties. Examples of release agents include carbamates, silicones and fluorocarbons. Illustrative examples of surface applied (i.e., topical) release agents include polyvinyl carbamates such as disclosed in U. S. Pat. No. 2.532.011 (Dahlquist et al.), reactive silicones. fluorochemical polymers, epoxysilicones such as are disclosed in U. S. Pat. Nos. 4,313,988 (Bany et al.) and 4,482,687 (Kessel et al.), polyorganosiloxane-polyurea block copolymers such as are disclosed in EP Pat. No. 0250248 Bl (Leir et al.), etc.

[0150] In one embodiment, the pressure sensitive adhesive article is a double-sided tape, featuring adhesive on opposite sides of a backing layer. The adhesives (i.e., a first adhesive layer and a second adhesive layer) on the two sides may be the same or different. The backing layer may be a film, a nonwoven web, paper, or a foam as further described below. The double-sided tape may comprise one or two release liners protecting the adhesive surface not in contact with the backing layer. In one embodiment, the adhesive layer is disposed between two release liners, which may be the same or different. In another embodiment, the adhesive layer is disposed on a backing and the opposing side of the backing comprises a release agent. The adhesive article is wound upon itself such that the exposed surface of the adhesive layer (opposite the backing) contacts the release-coated backing forming, for example, a roll of tape. Inyet another embodiment, the adhesive is disposed between a backing and release liner. In some embodiments, the adhesive tapes and articles do not contain a backing and therefore are freestanding adhesive layers. Transfer adhesive tapes are an example of such an adhesive article. Transfer adhesive tapes, also called transfer tapes, have an adhesive layer delivered on one or more release liners. The adhesive layer has no backing within it, so once delivered to the target substrate and the liner is removed, there is only adhesive. Some transfer tapes are multi-layer transfer tapes with at least two adhesive layers that may be the same or different. Transfer tapes are widely used in the printing and paper making industries for making flying splices, as well as being used for a variety of bonding, mounting, and matting applications both by industry and by consumers.

[0151] In a fourth aspect, another polymerizable composition is provided. The polymerizable composition comprises an adhesive precursor and a polymerizable ionic liquid of Formula I and / or of Formula II:R3 (I)

[0152] In each of Formula I and Formula II, Ri is independently H or methyl, and R₂ and R₃ are each independently linear or branched alkyl groups and / or ethoxy groups.

[0153] In some embodiments, a suitable polymerizable ionic liquid is of Formula III:o

[0155] In some embodiments, a suitable polymerizable ionic liquid is of Formula V:(V).

[0157] The adhesive precursor is not particularly limited. In some cases, the adhesive precursor may include components a), b), and c) of any embodiment of the polymerizable compositions described in detail herein. In some cases, the adhesive precursor may include polymerizable compositions that form (meth)acrylic pressure sensitive adhesives upon curing. In select cases, the adhesive precursor is selected to form an optically clear adhesive. Suitable exemplary adhesive precursors may comprise at least one alkyl (meth)acrylate monomer, a hydroxy-functional monomer, and an initiator (e.g., a photoinitiator).

[0158] Any suitable alkyl (meth)acrylate or mixture of alkyl (meth)acry lates can be used provided the glass transition temperature of the final (meth)acrylate polymer is sufficiently low (e.g., no greater than 20°C). Some alkyl (meth)acrylate monomers can be classified as low Tgmonomers based on the glass transition temperature of the corresponding homopolymers. The low Tgmonomers, as measured from the corresponding homopolymers, often have a Tgno greater than 20°C, no greater than 10°C, no greater than 0°C. or no greater than -10°C.

[0159] Suitable low Tgalkyl (meth)acrylate monomers include, but are not limited to. non-tertiary alky l acrylates but can be an alkyl methacry late having a linear alkyl group with at least four carbon atoms.Specific examples of alkyl (meth)acrylates include, but are not limited to. methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, sec-butyl acrylate, n-pentyl acrylate, 2-methylbutyl acrylate, n-hexyl acrylate, cyclohexyl acrylate, 4-methyl-2 -pentyl acrylate, 2-methylhexyl acrylate. 2-ethylhexyl acrylate, n-octyl acrylate, 2-octyl acrylate, isooctyl acrylate, isononyl acrylate, isoamyl acrylate, n-decyl acrylate, isodecyl acrylate, n-decyl methacrylate, lauryl acrylate, isotridecyl acrylate, n-octadecyl acrylate, isostearyl acrylate, n-dodecyl methacrylate, and combinations thereof In some embodiments, the low Tgalkyl (meth)acrylate is selected from 2-ethylhexyl acrylate, isooctyl acrylate, n-butyl acrylate. 2-methylbutyl acrylate, 2-octyl acrylate, and combinations thereof. Other suitable monomers include branched long chain acrylates, such as those described in U. S. Patent No. 8,137,807 (Clapper et al.). Additional suitable alkyl monomers include secondary alkyl acrylates, such as those described in U. S. Patent No. 9,102,774 (Clapper et al.).

[0160] Other alkyl (meth) acrylates that can be included in the polymerizable components are classified as high Tgmonomers based on the glass transition temperature of the corresponding homopolymers. The high Tgmonomers often have a Tggreater than 30°C, greater than 40°C, or greater than 0°C when homopolymerized (i.e., a homopolymer formed from the monomer has a Tggreater than 30°C, greater than 40°C, or greater than 0°C). Some suitable high Tgalkyl (meth)acrylate monomers include, for example, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, sec-butyl methacrylate, tert-butyl (meth)acrylate, cyclohexyl methacrylate, isobomyl (meth)acrylate, stearyl (meth)acrylate, and 3,3,5 trimethylcyclohexyl (meth)acrylate.

[0161] The amount of the alkyl (meth)acrylate can be any suitable amount up to 100 weight percent based on the total weight of the polymerizable components. The amount can be, for example, up to 99 weight percent, up to 95 weight percent, up to 90 weight percent, up to 85 weight percent, up to 80 weight percent, up to 75 weight percent, up to 70 weight percent, up to 65 weight percent, up to 60 weight percent, up to 55 weight percent, up to 50 weight percent, or up to 45 weight percent. The amount of the alkyl (meth)acrylate is often at least 35 weight percent, at least 40 weight percent, at least 45 weight percent, or at least 50 weight percent.

[0162] If the alkyl (meth) aery late is selected to include high Tgmonomers, the amount of this monomer is often no greater than 40 weight percent based on the total weight of polymerizable components. That is, the amount can be in a range of 0 to 40 weight percent based on the total weight of polymerizable components. If higher amounts are used, the overall Tgof the (meth) aery late polymer may be too high. The amount of the high Tgalkyl (meth)acrylate monomer is often no greater than 35 weight percent, no greater than 25 weight percent, or no greater than 15 weight percent. If present, the amount of the high Tgalkyl (meth)acrylate monomer is often at least 0.5 weight percent, at least 1 weight percent, at least 3 weight percent, at least 5 weight percent, or at least 10 weight percent. If the polymerizable component includes high Tgalkyl (meth)acrylate monomers, enough low Tgalkyl (meth)acrylate monomers is typically added to form a (meth)acrylate polymer with a Tgno greater than 20°C.

[0163] The alkyl (meth)acrylate monomer is typically selected to include a low Tgmonomer such as those that have a Tgno greater than -10°C when measured as a homopolymer. For example, the polymerizable components often contain at least 40 weight percent, at least 45 weight percent, at least 50 weight percent, at least 55 weight percent, at least 60 weight percent, at least 65 weight percent, or at least 70 weight percent and up to 95 weight percent, up to 90 weight percent, up to 85 weight percent, up to 80 weight percent, up to 75 weight percent, or up to 70 weight percent low Tgmonomer having a Tgno greater than -10°C when measured as a homopolymer. The amount is based on the total weight of polymerizable components. Suitable alkyl monomers that have a Tgno greater than -10°C when measured as a homopolymer include, but are not limited to. 2-ethylhexyl acrylate, isooctyl acrylate. N-butyl acrylate, 2-methylbutyl acrylate. 2-octyl acrylate, and combinations thereof.

[0164] Examples of suitable hydroxy-functional monomers include for instance and without limitation, 2 -hydroxy ethyl (meth)acrylate, 2-hydroxy-propyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate. and the like. In some embodiments, the polymerizable composition includes between about 0 and about 40 parts by weight of tire hydroxy -functional monomer, particularly between about 5 and about 35 parts, and more particularly between about 10 and about 30 parts.

[0165] Suitable initiators include any of the initiators described in detail above.

[0166] In a fifth aspect, an additional polymerizable composition is provided. The polymerizable composition comprises a) a C1-C18 alkyl (meth)acrylate ester monomer; and b) an ionic liquid, with the proviso that the polymerizable composition is essentially free of a carboxy lic acid-containing (meth)acrylate monomer.

[0167] As mentioned above, it was discovered that electrically debonded adhesion strength of adhesives containing acrylic acid and ionic liquids increased within 60 seconds after ending a voltage application. In contrast, compositions that lacked acrylic acid and contained either no polar monomers or only non-acidic polar monomers, did not exhibit increased adhesion strength within 60 seconds after voltage application.

[0168] In some cases, such polymerizable compositions further comprise a polyether macromer. Some suitable poly ether macromers include for instance and without limitation, macromers described in detail in PCT Publication No. WO 2023 / 275640 (Moughton et al.), incorporated herein by reference in its entirety.

[0169] Further optional components in the polymerizable compositions include various monomers, ionic liquids, etc., that are described in detail above with respect to the first aspect polymerizable compositions. Some variation in amounts of materials may’ be useful for these polymerizable compositions, e.g.. the Cl-18 alkyl (meth)acrylate ester monomer may be present in an amount of 15 wt.%-98 wt.%, a C5-C18 alkyl (meth)acrylate ester monomer may be present in an amount of 30 wt.%-90 wt.%, and / or a polymerizable ionic liquid may be present in an amount of 1 wt.%-50 wt.%, each based on a total w eight of poly merizable components. In certain cases, the polymerizable composition is substantially free of solvent.

[0170]

[0171] Select Embodiments of the Disclosure

[0172] In a first embodiment, the present disclosure provides a polymerizable composition comprising: a) a C1-C18 alkyl (meth)acrylate ester monomer; b) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components; c) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components; and d) an ionic liquid.

[0173] In a second embodiment, the present disclosure provides a polymerizable composition according to the first embodiment, wherein the combined amount of components b) and c) ranges from 10 wt.% to 45 wt.%, based on a total weight of polymerizable components.

[0174] In a third embodiment, the present disclosure provides a polymerizable composition according to the first embodiment or the second embodiment, wherein the second nitrogen-containing monomer is present in an amount of 5 wt.% to 25 wt.%, based on a total weight of polymerizable components.

[0175] In a fourth embodiment, the present disclosure provides a polymerizable composition according to any of the first through third embodiments, wherein a weight ratio of component b) to component c) is between 1 and 6.

[0176] In a fifth embodiment, the present disclosure provides a polymerizable composition according to any of the first through fourth embodiments, wherein the first nitrogen-containing monomer comprises at least one of N, N-dimethylacrylamide (NNDMA), N, N-diethylacrylamide (NNDEA), N, N-dimethylaminopropyl acrylamide (DMAPACM), N-tert-octyl-acrylamide (NTOA), N-octyl-acrylamide (NOA), acrylamide (Acm), 4-acryloylmorpholine (ACMO), N-isopropylacrylamide, (NIPAM), N-hydroxy ethyl acrylamide (NHEA), N-(isobutoxymethyl)acrylamide (NIBMA), N-tert-butylacrylamide (NTBA), N-(3-methoxypropyl)acrylamide (NMPA). or sulfopropyl acrylamide N-butyl-N '-methyl imidazolium.

[0177] In a sixth embodiment, the present disclosure provides a polymerizable composition according to any of the first through fifth embodiments, further comprising an ethoxy group-containing (meth)acrylate monomer in an amount of 5 wt.% to 50 wt.%, based on a total weight of polymerizable components.

[0178] In a seventh embodiment, the present disclosure provides a polymerizable composition according to any of the first through sixth embodiments, wherein the C 1 -C 18 alkyl (meth)acrylate ester monomer comprises a C8 acrylate in an amount of 30 wt.% or greater, based on a total weight of polymerizable components.

[0179] In an eighth embodiment, the present disclosure provides a polymerizable composition according to any of the first through seventh embodiments, further comprising at least one additive selected from the group consisting of an adhesion promoter (e.g. glycidyl propyl trimethoxy silane), a stabilization agent (e.g. calcium carbonate), a corrosion inhibitor (e.g. benzotriazole or 2-(methacry loy loxy)ethy 1 acetoacetate), a conducting salt (e.g. lithium bis(fluorosulfonyl)imide. sodium hexafluorophosphate), and a polymer having a glass transition temperature of at least 40 degrees Celsius (e.g. polyvinyl butyral).

[0180] In a ninth embodiment, the present disclosure provides a polymerizable composition according to any of the first through eighth embodiments, further comprising a filler comprising a plurality of hollow glass microspheres, a plurality of polymeric microparticles, a plurality of polymeric nanoparticles each comprising an interior region comprising a polymer having a glass transition temperature below room temperature and an outer shell comprising a polymer having a glass transition temperature of at least 50°C, an organo-phosphinate. a plurality of alumina particles, a plurality of pre-expanded hollow polymeric microspheres, a plurality of conductive particles, or combinations thereof.

[0181] In a tenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through ninth embodiments, further comprising a carboxylic acid-containing (meth)acrylate monomer in an amount of less than 2 parts per hundred parts resin (phr) of the polymerizable composition.

[0182] In an eleventh embodiment, the present disclosure provides a polymerizable composition according to any of the first through tenth embodiments, further comprising a (meth)acrylate macromer comprising one or more of a poly(ethylene oxide) group, a polypropylene oxide) group, a poly(ethylene oxide-co-propylene oxide group, a poly(tetrahydrofuran) group; a poly (ester) group, or combinations thereof.

[0183] In a twelfth embodiment, the present disclosure provides a polymerizable composition according to any of the first through eleventh embodiments, containing less than 0.1 wt.% of a hydroxyl-containing (meth)acrylate monomer, based on a total weight of polymerizable components.

[0184] In a thirteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through twelfth embodiments, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises at least one of 2-ethylhexyl acrylate, n-butyl acry late, 2-methylbutyl acrylate, n-hexyl acrylate, or 6-methylheptyl acrylate.

[0185] In a fourteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through thirteenth embodiments, wherein the C1-C18 alkyl (meth)acrylate ester monomer is present in an amount of 15 wt.% to 90 wt.%, based on a total weight of polymerizable components.

[0186] In a fifteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through fourteenth embodiments, wherein the Cl -Cl 8 alkyl (meth)acrylate ester monomer comprises a C6-C 18 ( eth) aery late ester monomer present in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

[0187] In a sixteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through fifteenth embodiments, wherein the second nitrogen-containing monomer comprises at least one of N-vinyl pyrrolidone, vinyl methyl oxazolidinone. or N-vinyl caprolactam, N-vinyl imidazole, N-vinyl carbazole, N-vinyl formamide. N-methyl-N-vinyl acetamide, N-vinyl piperidone, or N-vinyl-imidazolium bis(fluorosulfonyl)imide.

[0188] In a seventeenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through sixteenth embodiments, wherein the ionic liquid comprises apolymerizable ionic liquid that is present in an amount of 1 wt.% to 30 wt.%, based on a total weight of polymerizable components.

[0189] In an eighteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through seventeenth embodiments, wherein the ionic liquid comprises a non-polymerizable ionic liquid that is present in an amount of 2 parts per hundred parts resin (phr) to 20 phr.

[0190] In a nineteenth embodiment, the present disclosure provides a polymerizable composition according to any of the first through eighteenth embodiments, wherein the ionic liquid comprises at least one of a sulfate, a sulfonate, a carboxylate, a phosphate, a borate, a phenyl borate, an oxalato borate, a nitrate, an imide, a sulfidoimide, a dicyanamide, a tricyanomethanide, or a halide ion.

[0191] In a twentieth embodiment, the present disclosure provides a polymerizable composition according to any of the first through nineteenth embodiments, wherein the ionic liquid comprises at least one of an imidazolium, an ammonium, a pyridinium, a phosphonium, a sulfonium, or an iodonium ion.

[0192] In a twenty -first embodiment, the present disclosure provides a polymerizable composition according to any of the first through twentieth embodiments, further comprising a crosslinker.

[0193] In a twenty-second embodiment, the present disclosure provides an at least partially polymerized reaction product of the polymerizable composition according to any of the first through twenty -first embodiments.

[0194] In a twenty-third embodiment, tire present disclosure provides a pressure sensitive adhesive article comprising an adhesive composition comprising the at least partially polymerized reaction product according to the twenty-second embodiment, wherein the adhesive composition is disposed on at least a portion of a substrate.

[0195] In a twenty-fourth embodiment, the present disclosure provides an adhesive article according to the twenty -third embodiment, wherein the substrate is a liner comprising a release agent, a backing, or a carrier.

[0196] In a twenty -fifth embodiment, the present disclosure provides an adhesive article according to the twenty-third embodiment or the twenty -fourth embodiment, further comprising a second adhesive layer, wherein the substrate is a carrier and the substrate is disposed between the adhesive composition and the second adhesive layer.

[0197] In a twenty-sixth embodiment, the present disclosure provides an adhesive article according to the twenty -fourth embodiment or the twenty-fifth embodiment, wherein the carrier comprises a conductive material, optionally w herein the conductive material comprises a carbon-based material.

[0198] In a twenty -seventh embodiment, the present disclosure provides an adhesive article according to any of the twenty -third through twenty-sixth embodiments, wherein the adhesive composition exhibits a tensile pushout strength of greater than 0.2 megaPascals (MPa), as determined by the Tensile Pushout Test Method.

[0199] In a twenty-eighth embodiment, the present disclosure provides an adhesive article according to any of the twenty -third through twenty -seventh embodiments, wherein the adhesive composition exhibitsa decrease in tensile pushout strength of at least 50% following subjection to 9 volts (V), 10 V, 20 V, 30 V, 40 V, or 50 V, for one minute, as determined by the Tensile Pushout Test Method.

[0200] In a twenty -ninth embodiment, the present disclosure provides an adhesive article according to any of the twenty -third through twenty-eighth embodiments, wherein the adhesive composition exhibits a decrease in peel strength of at least 50% following subjection to 50 volts (V) for one minute, as determined by the Peel Adhesion Test Method.

[0201] In a thirtieth embodiment, the present disclosure provides an adhesive article according to any of the twenty -third through twenty -ninth embodiments, wherein the adhesive composition exhibits a decrease in peel strength of at least 50% following subjection to 10 volts (V) for 5 seconds. 10 seconds, 20 seconds, 30 seconds, 45 seconds, or 60 seconds, as determined by the Peel Adhesion Test Method.

[0202] In a thirty -first embodiment, the present disclosure provides an adhesive article according to any of the tw enty-third through thirtieth embodiments, wherein the at least partially polymerized reaction product comprises a polymer that is a polymerized reaction product of at least components a), b), and c).

[0203] In a thirty -second embodiment, another polymerizable composition is provided. The polymerizable composition comprises an adhesive precursor and a polymerizable ionic liquid of Formula I and / or of Formula II. In each of Formula I and Formula II, Ri is independently H or methyl, and R2 and Rs are each independently linear or branched alkyl groups and / or ethoxy groups.

[0204] In a thirty-third embodiment, the present disclosure provides another polymerizable composition. The polymerizable composition comprises a) a Cl -Cl 8 alkyl (meth)acrylate ester monomer and b) an ionic liquid. The polymerizable composition is essentially free of a carboxylic acid-containing (meth)acrylate monomer.

[0205] In a thirty-fourth embodiment, the present disclosure provides a polymerizable composition according to the thirty -third embodiment, further comprising: c) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components; d) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has anitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components, with the proviso that the ionic liquid may comprise functionality of the first nitrogen-containing monomer to provide both component b) and component c) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component b) and component d).

[0206] In a thirty -fifth embodiment, the present disclosure provides a polymerizable composition according to the thirty -third embodiment or the thirty -fourth embodiment, containing less than 0.1 wt.% of a hydroxyl-containing (meth)acrylate monomer, based on a total weight of polymerizable components.

[0207] In a thirty-sixth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through thirty -fifth embodiments, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises a C8 acr late in an amount of 30 wt.% or greater, based on a total weight of polymerizable components.

[0208] In a thirty -seventh embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through thirty-sixth embodiments, wherein the Cl -Cl 8 alkyl (mcth)acrylatc ester monomer comprises at least one of iso-octy l acry late, 2-cthylhcxyl acrylate, n-buty 1 acry late, 2-methylbutyl acry late, methyl acrylate, n-hexy I acry late, n-octy 1 acrylate, or 6-methylheptyl acrylate.

[0209] In a thirty -eighth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty-third through thirty -seventh embodiments, wherein the C1-C18 alkyl (meth)acrylate ester monomer is present in an amount of 15 wt.% to 98 wt.%, based on a total weight of polymerizable components.

[0210] In a thirty -ninth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through thirty-eighth embodiments, wherein the Cl -Cl 8 alkyl (meth)acrylate ester monomer comprises a C5-C18 (meth)acrylate ester monomer present in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

[0211] In a fortieth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through thirty -ninth embodiments, wherein the ionic liquid comprises a polymerizable ionic liquid that is present in an amount of 1 wt.% to 50 wt.%. based on a total weight of poly merizable components.

[0212] In a forty -first embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through fortieth embodiments, wherein the ionic liquid comprises a non-polymerizable ionic liquid that is present in an amount of 2 parts per hundred parts resin (phr) to 20 phr.

[0213] In a forty-second embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through forty-first embodiments, wherein the ionic liquid comprises at least one of a sulfate, a sulfonate, a carboxylate, a phosphate, a borate, a phenyl borate, an oxalato borate, a nitrate, an imide, a sulfidoimide, a dicyanamide, a tricyanomethanide, or a halide ion.

[0214] In a forty -third embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through fort -second embodiments, wherein the ionic liquidcomprises at least one of an imidazolium, an ammonium, a pyridinium, a phosphonium, a sulfonium, or an iodonium ion.

[0215] In a forty -fourth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through forty-third embodiments, wherein the polymerizable composition is substantially free of solvent.

[0216] In a forty -fifth embodiment, the present disclosure provides a polymerizable composition according to any of the thirty -third through forty -fourth embodiments, further comprising a poly ether macromer.EXAMPLES

[0217] Unless otherwise noted or readily apparent from the context, all parts, percentages, ratios, etc. in the Examples and the rest of the specification are by weight. Table 1 (below) lists materials used in the examples and their sources:Table 1. Materials ListAbbreviation Description2-EHA 2-etliylhexyl acry late, obtained from BASF, Florham Park, New Jersey, USA 2-HEA 2-hydroxyethyl acrylate, obtained from BASF, Florham Park, New Jersey, USA HBA 4-hydroxybutyl acrylate, obtained from BASF, Florham Park, New Jersey, USA BA n-Butyl acrylate, obtained from BASF. Florham Park, New Jersey, USAHA n-Hexyl aery late, obtained from BASF, Florham Park, New Jersey, USA2 -methoxy ethyl acrylate, obtained from Millipore Sigma, Burlington, 2MOEAMassachusetts, USA2-[2-(2-Methoxyethoxy)ethoxy]ethyl acrylate, obtained from Millipore Sigma, M(EO)2EABurlington, Massachusetts, USA2-Ethylhexyl diglycol acrylate, obtained from Miwon Specialty Chemical M1086Company, Columbia. South Carolina, USAHydroxy -ethyl-caprolactone acrylate having a molecular weight of 436 Da, HECLAobtained from BASFACAC-MA 2-(Methacryloyloxy)ethyl acetoacetate, obtained from Millipore Sigma,Burlington. Massachusetts, USAAA Acrylic acid, obtained from BASF, Florham Park, New Jersey, USA NNDMA N, N-dimethylacrylamide, obtained from TCI America. Portland, OR, USA TOACM Tert-octyl acrylamide, obtained from Nouryon-USA, Houston, Texas, USA ACM Acry lamide, obtained from TCI America, Portland, OR, USAACMO 4-Acryloylmorpholine, obtained from TCI America, Portland, OR, USA NVP N-vinyl pyrrolidone, obtained from TCI America, Portland, OR, USANVC N-vinyl carbazole, obtained from TCI America, Portland, OR, USAVMOX Vinyl methyl oxazolidinone, obtained from TCI America. Portland, OR. USA NVIMID N-vinyl-imidazole, obtained from TCI America, Portland, OR, USABZT Benzotriazole, obtained from Millipore Sigma, Burlington, Massachusetts, USA C18 Guerbet alcohol derived acry late from 3M, monomer GM-4 disclosed in C18AUS8137807B2Polyethylene glycol) methyl ether acrylate, Mn = 550 Da obtained from Osaka PEG-AOrganic Chemicals / San Esters, Osaka, JapanMBS core-shell rubber nanoparticle, sold under the trade name Clearstrength XT 100XT 100, obtained from Arkema. Colombes, FranceA hollow pre-expanded polymeric microsphere sold under the trade name, EMS Dualite E0135-040D, obtained from Chase Corporation, Westwood.Massachusetts, USAPoly(methyl methacrylate), (PMMA) particles with a narrow particle size MX-80H3wT distribution of 0.8 pm, sold under the trade name MX-80H3wT. obtained from Soken Chemical Asia Co. Ltd., Tokyo, JapanCarbon black dispersion with 30 wt.% carbon black (ca. 200 mn) dispersed in CB 1BOA (isobornyl acry late) and HDDA (1,6-hexanediol-diacrylate), obtained from Penn Color, Hatfield, Pennsylvania, USANickel coated graphite microparticles with diameter ca. 55 pm, sold under the EF2806 trade name E-fill 2806, obtained from Oerlikon Metco (US) Inc., Westbury, New Jersey, USAPolyvinyl butyral, (PVB) copolymer with a glass transition temperature of 63 °C, B30HH sold under trade name Mowital B30HH. obtained from Kuraray America, Inc.,Houston, Texas, USAA copolymer of l-vinyl-2-pyrrolidone and vinyl acetate in a ratio of 6:4 by mass KVA64 with a weight averaged molecular weight of -50.000 g / mol. sold under the trade name of Kollidon VA 64, obtained from BASF, Florham Park, New' Jersey, USA PMMA-nBA-PMMA acrylic block copolymer having a molecular weight of ca. LA4285 60 kDa and 50% PMMA, obtained rmder the trade designation “KURARITY LA4285” from Kuraray Co., Ltd., Tokyo, JapanAluminum diethyl phosphinate particles, sold under the trade name Exolit OP OP 930930, obtained from Clariant (US) Inc., Charlotte, North Carolina, USA iM 16K.-MAS is a hollow glass microsphere with a diameter of ca. 60 pm, a iM16K-MAS density of 0.46 g / cc, and a crush strength of 16,000 psi which w as prepared by surface functionalizing iM16K hollow glass microspheres with methacrylicgroups prepared as per US11518914B2. iM16K hollow glass microspheres were obtained from 3M Company, St. Paul, Minnesota, USAsK15 is a hollow glass microsphere with a diameter of ca. 115 pm, a density of 0.16 g / cc, and a crush strength of 300 psi which was prepared by surface sK15 functionalizing KI 5 hollow glass microspheres with C 16 alkyl chain groups as per US11518914B2. K15 hollow glass microspheres were obtained from 3M Company, St. Paul, Minnesota, USAS4630 is a hollow glass microsphcrc with a diameter of ca. 40 pm, a density of S4630 0.46 g / cc, and a crush strength of 16,000 psi obtained from 3M Company, St.Paul, Minnesota, USAHDDMA 1,6-hexanediol-dimethacrylate, obtained from Arkema, Colombes, France 2,2-Dimethoxy-l,2-diphenylethan-l-one, sold under the trade name Irgacure Irg 651651, obtained from Ciba Specialty Chemicals, Bassel, Switzerland Pentaerythritol tetrakis(3 -mercaptopropionate), obtained from MilliporeSigma, PTMPBurlington, Massachusetts, USAN, N. N-Trimethyl ammonium ethyl acrylate bis(fluorosulfonyl)imide, TMAEA FSI synthesized as described for DMAEAM FSI by Moughton et al in W02023 / 228050 AlN, N. N-Trimethyl ammonium ethyl acrylate bis(trifluoromethane sulfonyl)imide. TMAEA TFSIsynthesized as “POS-1” described by Klun et al in US11111392 B2 Sulfopropyl acry late N-butyl-N'-methyl imidazolium synthesized as described SPA BMIherein.Sulfopropyl acrylate N-octyl-N'-methyl imidazolium synthesized as described SPA OMIherein.Sulfopropyl acrylamide N-butyl-N'-methyl imidazolium synthesized as described SPACM BMIherein.2-hydroxy ethyl methyl imidazolium chloride was obtained from lo-Li-Tec, HEMI ClHeilbronn, Germany.Sodium hexafluro phosphate was obtained from MilliporeSigma, Burlington, NaPF6Massachusetts, USAHydroxy ethyl methyl imidazolium hexafluorophosphate synthesized as HEMI PF6described herein.An adduct of 2-isocyanatocthyl acry late and hydroxy ethyl methyl imidazolium IEA HEMI PF6hexafluorophosphate synthesized as described herein.IEA Isocyanatoethyl acrylate obtained from TCI AmericaSPAK Sulfopropyl acrylate potassium salt, obtained from TCI America2-Acrylamido-2-methyl-l -propanesulfonic acid sodium salt solution, obtained SPAC Nafrom MilliporeSigma, Burlington, Massachusetts, USABMI C1 N-Butyl-N'-methyl-imidazolium chloride, obtained from TCI America,l-Methyl-3-octylimidazolium chloride, obtained from Sigma Aldrich, St. Louis, OMI ClMissouri, USA1-bromohcxanc, CAS 111-25-1, obtained from Thermo Scientific, Waltham, C6BrMA, USA2-(dimethylamino)ethyl acrylate, CAS 2439-35-2, obtained from DMAEAMilliporeSigma, Burlington, Massachusetts, USATEMPO 2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6, 6-Tetramethyl-l-piperidinyloxy, free radical, CAS 2564-83-2, obtained from Sigma-Aldrich, St Louis, MO, USA Lithium bis(fhiorosulfonyl)imide, CAS 171611-11-3, obtained as FORANEXT LiFSIrMLiFSI, obtained from Arkema, Pierre-Benite, FranceAnhydrous magnesium sulfate, obtained from MilliporeSigma, Burlington, MA, MgSO4USAN-hexyl-N, N-dimethyl-ammonium ethyl acrylate bis(fluorosulfonyl)imide, HDMAEA FSIsynthesized as described hereinN-butyl-N -methylimidazolium hexafluorophosphate, obtained fromBMI PF6MilliporeSigma, Burlington, Massachusetts, USABMI TFSI l-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, obtained from MilliporeSigma, Burlington, Massachusetts, USAN-butyl- N'-methylimidazolium bis(fluorosulfonyl)imide, obtained from BMI FSIMilliporeSigma, Burlington, Massachusetts, USATriethylsulfonium bis(trifhioromethylsulfonyl)imide, obtained fromTES TFSIMilliporeSigma, Burlington, Massachusetts, USATBMA FSI Tributylmethylammonium bis(fluorosulfonyl)imide, obtained from loLiTec, Heilbronn, GermanyTBMP FSI Tributylmethylphosphonium bis(fluorosulfonyl)imide, obtained from loLiTec,Heilbronn, Germany3M™ VHB™ Electronic Tape 86415 is a 0.15 mm (0.006 in) black, acrylic foam 3M VHB 86415 tape used for bonding a wide range of materials in the electronics industry.Obtained from 3M Company, St. Paul, Minnesota, USA3M™ VHB™ Tape 4941 is a 1.125 mm (0.045 in) thick gray double sided 3M VHB 4941 conformable acrylic foam tape used to bond a wide range of substrates. Obtained from 3M Company, St. Paul, Minnesota, USA3M™ VHB™ Tape 4950 is a 1,125 mm (0.045 in) thick double sided acrylic 3M VHB 4950 tape with a firm foam core that offers high strength and vibration / fatigue resistance. Obtained from 3M Company. St. Paul, Minnesota, USAAn omnidirectional conductive sponge 0.3 mm thick from Yufreyoo based on Conductive polyurethane foam sponge with electrodeposited nickel, copper, and other metals Foam-1 to make the sponge conductive in all directions. Surface resistance: 0.05 Q.Obtained from Yufreyoo, Sichuan, China.Super P Carbon Conductive carbon black (>96% carbon black) obtained from Irncrys, Paris, Black FranceSolvent-free wetting and dispersing additive for dispersing and stabilizing BYKJET 9152 organic pigments and carbon blacks in solvent-borne obtained from BYK, Wesel,Germany3M VHBSolvent based primer used to promote adhesion to polypropylene. ABS.UniversalPET / PBT. obtained from 3M Company. St. Paul, MN, USAPrimer2-mil (50 pm) biaxially oriented PET film from 3M Company, St. Paul, MN was Plasma Treatedplasma treated (as per conditions described in U. S. Pat. No. 10,134,566 (David et 2 mil PET Filmal.)50 micron PET with a coating of aluminum on one side, obtained as Mylar film Al PETfrom HFS, Azusa, CA USA2 mil thick PET release liner, obtained under product name RF12N from SKC, RF12NSeoul, Korea2 mil thick PET release liner, obtained under product name RF02N from SKC, RF02NSeoul, Korea

[0218] Preparation of HDMAEA FSI

[0219] A 500 mL 3-necked flask equipped with an overhead stirrer was charged with C6Br (101.80 g.0.6167 mol), TEMPO (38 mg), and NNDMAEA (88.31 g, 0.61671 mol) and placed in a 95 °C oil bath for about 16 hours. After that time, an aliquot was analyzed by 'H NMR and found to have no NNDMAEA, but about 4 mole percent of the initial C6Br remained. To the flask was added NNDMAEA (4.42 g, 0.0308 mol), and the reaction was heated at 105 °C for an additional 16 hours. After that time, an aliquot was analyzed by1H NMR and found to have no NNDMAEA or C6Br. The product, N-hexyl- N. N-dimethyl-ammonium ethyl acrylate bromide was a solid at room temperature.

[0220] A 3-necked 250mL flask equipped with overhead stirrer was charged with N-hexyl-N, N-dimethyl-ammonium ethyl acry late bromide (50.38 g, 0.1634 mol equivalents. 308.26 equivalent weight) and about 67 g water, and was heated in a 67 °C bath until the material dissolved. Next LiFSI (33.63g, O.0.180 equivalents) was dissolved in 33.7 g of water, and was added to the flask with stirring for 10minutes, which turned the solution milky. Upon separation of the layers, a lower whitish layer formed. This lower layer was stirred with 105 g of water at 67 °C for 10 minutes. Upon separation, the lower organic layer was dried over 8.5 g MgSOj. fdtered and concentrated on a rotary evaporator at aspirator pressure for 60 minutes at 60 °C, then at about 70 °C for 60 minutes at 133 Pascals to provide the product as a viscous liquid.Preparation of SPA BMIA round bottom flask was equipped with a TEFLON-coated stir bar and charged with 3-sulfopropyl acrylate potassium salt (10 g), l-butyl-3-methylimidazolium chloride (7.52g). and deionized water (10 g). The solution was stirred for 15.5 hours and then was precipitated into 900 mL of acetone. The solvent was filtered through a bed of celite. The solvent was removed by rotary evaporation under reduced pressure to yield SPA BMI as a clear liquid, which was further dried under a stream of air. ’H-NMR (500 MHz; DMSO-de): 5 9.24 (s, 1H), 7.81 (t, J= 1.8 Hz. 1H), 7.74 (t. J= 1.7 Hz, 1H). 6.30 (dd, J= 17.3. 1.6 Hz, 1H). 6.16 (dd,.7= 17.3, 10.3 Hz, 1H), 5.93 (dd, J= 10.3, 1.6 Hz, 1H), 4.19-4.16 (m, 4H). 3.86 (s, 3H). 2.50 (dd, J= 8.3, 6.8 Hz. 2H), 1.94-1.88 (m, 2H), 1.79-1.73 (m, 2H), 1.24 (dq, J= 15.0, 7.5 Hz, 2H).0.88 (t, J = 7.4 Hz, 3H). 13-C NMR (126 MHz; DMSO): 5 165.6, 136.7, 131.4, 128.4, 123.7, 122.3, 63.6, 48.5, 47.9, 35.7, 31.5, 24.9, 18.8, 13.3.Preparation of SPA OMIA round bottom flask was equipped with a TEFLON-coated stir bar and charged with 3-sulfopropyl acrylate potassium salt (10 g), l-octyl-3-methylimidazolium chloride (9.93g), and deionized water (15 g). The solution was stirred for 48hours and then was precipitated into 900 mL of acetone. The solution was filtered through filter paper and removed by rotary evaporation under reduced pressure to yield SPA OMI (14.25 g, 85% yield) as a clear liquid. ’H-NMR (500 MHz; DMSO-de): 5 9.22 (s, 1H), 7.81 (t, J= 1.8Hz, 1H), 7.74 (t. J = 1.7 Hz, 1H). 6.31 (dd, J= 17.3. 1.6 Hz, 1H). 6.17 (dd, J= 17.3. 10.3 Hz, 1H), 5.94 (dd. J= 10.3, 1.6 Hz. 1H), 4.17 (td. J = 7.0, 3.8 Hz, 4H).3.87 (s, 3H). 2.52-2.49 (m. 2H), 1.94-1.89 (in.2H). 1.78 (quintet, J = 7.2 Hz. 2H), 1.29-1.20 (m, 10H), 0.85 (t. J= 7.0 Hz, 3H). 13-C NMR (126 MHz; DMSO): 8 165.5. 136.7, 131.4, 128.4, 123.6. 122.3. 63.6. 48.8, 47.9, 35.7. 31.2, 29.5, 28.6. 28.4, 25.6, 24.9, 22.1, 14.0.Preparation of SPACM BMIA round bottom flask was equipped with a TEFLON-coated stir bar and charged with 2-acrylamido-2-methyl-1 -propanesulfonic acid sodium salt solution (30 g of a 50 wt.% solution in water) and l-butyl-3-methylimidazolium chloride (11.42 g). The solution was stirred for 48 hours and then was precipitated into 900 mL of acetone. The solution was filtered and removed by rotary evaporation under reduced pressure to yield SPACM BMI (21.2 g, 96% yield) as a clear liquid. 'H-NMR (500 MHz; DMSO-ds): 8 9.20 (s, 1H), 8.37 (s, 1H). 7.80 (t, J = 1.7 Hz, 1H), 7.73 (t, J= 1.7 Hz, 1H), 6.07 (dd, J = 17.1, 10.0 Hz, 1H). 5.96 (dd, J= 17.1. 2.2 Hz, 1H), 5.50 (dd, J= 10.0, 2.2 Hz, 1H), 4.18 (t. J = 7.2 Hz, 2H), 3.87 (s, 3H). 2.78 (s, 2H), 1.79-1.73 (m. 2H), 1.44 (s, 6H), 1.25 (dd, J= 15.1, 7.5 Hz, 2H), 0.89 (t, J= 7.4 Hz.3H). 13-C NMR (126 MHz; DMSO): 8 163.8, 136.7. 133.4, 124.0, 123.7, 122.3. 60.0, 51.7, 48.5, 35.8, 31.5, 26.1, 18.8, 13.3.Preparation of HEMI PF62-hydroxy ethyl methyl imidazolium chloride, HEMI Cl (10.00 g. 0.0615 mol) was dissolved in 2.5 g water in a reaction flask. A beaker was charged with NaPFe (10.33 g, 0.0615 mol) and 2 g of DI water to make a slurry, which was then added the jar. and the reaction was magnetically stirred for 2h. Next dichloromethane (25 g) was added to the jar and after stirring for a few minutes, the contents of the jar were poured into a separately funnel. After separation, the lower layer was concentrated on a rotary evaporator for 30 min at 65C to provide the hydroxy ethyl methyl imidazolium hexafluorophosphate, HEMI PF6 as a clear oil.Preparation of IEA HEMI PF6In a 50 rnL flask. 20 parts of HEMI PF,,. 0.001 parts each of BHT and MEHQ were charged, followed by the addition of 8.5 parts of isocyanato ethyl acrylate. The reaction mixture was stirred using a magnetic stirrer. As the reaction progressed, the temperature rose to approximately 30°C. The mixture was stirred at this temperature for 30 minutes and then heated to 50 °C on a hot plate. The reaction was maintained at 50 °C for one hour. IR analysis showed the absence of the isocyanate peak, confirming the formation of the HEMI IEA PF6adduct.Preparation of Conductive Primer-1 on PET Liner3M VHB Universal Primer UV was used as received and Super P conductive carbon black and BYKJET 9152 dispersant were both mixed into the primer at 4000 rpm using a Dayton Lab Mixer. The carbon black and dispersant were both added at 2.5 wt.% each to give a conductive primer composition of 95 / 2.5 / 2.5 by wt.% of primer solution / carbon black / dispersant. The conductive primer solution was coated onto RF12N PET liner and dried at 70 °C for 5 minutes to obtain a dry conductive primer thickness of 7 microns. The dried conductive primer was then used to transfer (laminate) onto the electrically debondable adhesives E49-E53 to make ML-E1 through ML-E8.Test Methods

[0221] Peel Adhesion Testing (“Peel Adhesion Test Method”)For all peel adhesion testing, the easy side, RF02N release liner (SKC Haas Display Films LLC, Seoul KR) was removed, and the exposed side of the tacky adhesive transfer tape was rolled by hand lamination using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek, NY) onto a 6 inch (15 cm) wide primed polyester film backing (3M Company. St. Paul, MN). 2-mil (50 pm) biaxially oriented PET film with plasma treatment (conditions described in U. S. Pat. No. 10,134.566 (David et al.)) ensuring no air bubbles were trapped between the adhesive and the primed polyester film. Peel adhesion was measured at an angle of 180 degrees. Peel adhesion testing was performed on annealed 18-gauge, 304 stainless steel (“SS”) from Chem. Instruments, Fairfield, OH). The RF12N release liner (SKC Haas Display Films LLC, Seoul KR) was removed from the tapes on PET backings and the adhesives were laminated directly to the 2-inch x 6-inch (5.08 cm x 15.24 cm) substrate using a weighted rubberized (4.5 lb, 2.04 kg) hand roller with four repetitions of 3-second roll downs. This method followed ASTM D3330 / D3330M-04(2018), test method A, liner side, except for samples E71-E79 and CE27-CE30, which followed ASTM D3330, test method E, liner side. All samples and substrates were conditioned in a controlled temperature and humidity (“CTH”) room (set at 23°C, 50% RH (relative humidity)) prior to peel testing. SS test panels were cleaned with methyl ethyl ketone before and after testing. Peel testing was doneusing an SP-2300 iMass (iMass Inc., Accord, MA USA) at a rate of 12 inches / min (0.3 m / min) after a dwell time of 1 day.

[0222] Electrical Debonding Peel TestingFor electro debonded peel adhesion testing for multi-layer samples (i.e. ML-E1 through ML-E8), the same test method was used as described above for peel adhesion testing, except a 20 min dwell on SS in a CTH room was used instead of 1 day dwell in a CTH room. Also, the electrically debondable PSA skin composition (i.e. E49 through E53 adhesive composition) was laminated within the multi-layer tape to directly contact the stainless steel surface to facilitate electrical debonding of that adhesive side from the stainless steel substrate. To electrically debond the peel adhesion samples, a BK Precision 1685 B power source was connected to the conductive B core layer within the multi-layer tape (e.g. conductive foam-1 in ML-E2) and the SS panel via a positive and negative electrode, respectively. For 60 seconds, a voltage of 50 V was applied across the adhesive tape conductive core layer and the SS substrate. Immediately after this time, the samples were disconnected from the power source electrodes and loaded onto an iMass peel tester using an SP-2300 iMass (iMass Inc., Accord, MA USA) and tested for 180-degree peel adhesion at a rate of 12 inches / min (0.3 m / min) after a total dwell time of 20 minutes, excluding the 1 minute debonding time.For electro debonded peel adhesion testing for samples E65-E70, the same test method was used as described above for ‘peel adhesion testing’, except a 30 min dwell on SS in a CTH room was used instead of 1 day dwell in a CTH room. Also, instead of a 2 mil plasma primed PET backing, the adhesive was laminated to the conductive side of Al PET). To electrically debond the peel adhesion samples, a BK Precision 1685 B power source was connected to the Al PET and the SS panel via a positive and negative electrode, respectively. For 5-20 seconds, a voltage of 10 V was applied across the Al PET and the SS substrate. Immediately after this time, the samples were disconnected from the power source electrodes and loaded onto an iMass peel tester using an SP-2300 iMass (iMass Inc., Accord, MA USA) and tested for 180-degree peel adhesion at a rate of 12 inches / min 30 (0.3 m / min) after a total dwell time of 30 minutes, excluding the 5-20 second debonding time.For electro debonded peel adhesion testing for E71-E79 and CE27-CE30, the same test method was used as described above for peel adhesion testing, except samples were prepared on 2 mil reflective Mylar film (HFS, Azusa, CA USA). The conductive side of the Mylar film was laminated to be in contact with the electrically debondable adhesive. Additionally, a 30 min dwell on SS in a CTH room was used instead of 1 day dwell in a CTH room. The adhesive / Mylar construction bonded to the stainless steel panel was loaded onto an iMass peel tester using an SP-2300 iMass (iMass Inc., Accord, MA USA). To electrically debond the peel adhesion samples, a BK Precision 1685 B power source was connected to the conductive side of the Mylar backing and the SS panel via a positive and negative electrode, respectively. For 30 seconds, a voltage of 10 V or 50 V was applied across the Mylar backing and the SS substrate.Immediately after this time, the samples were disconnected from the power source electrodes. After 10 or 60 seconds, the sample was tested forl80-degree peel adhesion at a rate of 12 inches / min (0.3 m / min).

[0223] Electrical Debonding Tensile Pushout Testing (“Tensile Pushout Test Method”)The experimental setup is represented in FIG. 2. A stainless-steel coupon (40 mm x 40 mm x 3 mm) containing a hole in the center (diameter = 24 mm) and a circular stainless-steel puck (diameter = 33 mm, 3 mm thick) were adhered using a ring-shaped adhesive (outer diameter = 31 mm, inner diameter = 26 mm, at a thickness of 2, 4, 8, or 14 mil). Samples were weighed down with 8 kg for 30 seconds at 23°C and dwelled for 1 day at controlled temperature and humidity conditions (23 °C / 50% RH). Then, a BK Precision 1685 B power source was connected to the coupon and puck via a positive and negative electrode, respectively. For 60 seconds, (or 300 seconds for CE20 and CE21) a voltage of 50 V (or 9 V for E55-E64) was applied across the coupon and puck. Immediately after this time, the samples were disconnected from the power source electrodes and loaded onto an MTS Criterion. The puck was pushed out from the coupon in the direction shown in FIG. 2 at a rate of 10 mm / min (crosshead speed). The peak stress (in the stress vs. strain curve) required to remove the puck from the coupon was recorded in MPa. Samples w here no voltage was applied were also tested in this way and the peak stress for these measurements are reported in Table 4 as “Initial peak stress (MPa)".

[0224] High temperature (70 °C) Static Shear TestingThe adhesive transfer tapes (i.e. E1-E64. CE1-CE25) were cut to be 1” W by 1” L in size. The RF02N liner was removed and the transfer tape was laminated by hand using a using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek, NY) onto a 1” W x 3” L plasma primed polyester film backing (3M Company, St. Paul. MN, 2-mil / 50 pm biaxially oriented PET film) ensuring no air bubbles were trapped between the adhesive and the primed polyester film and positioning the adhesive at one end of the PET backing, ensuring a 1” by 1” overlap area. The RF12N liner was then removed and the 1” by T’ overlap area of adhesive w as laminated to a 2” W by 3” L SS panel. The adhesive was laminated to the panel ensuring it was positioned in parallel to the edges of the panel and positioned centrally. The lower 2” L portion of the PET backing was looped back on itself to form a 1“ laminated fold. This portion of backing was then stapled together to form a l’’ loop to hang the weight during high temperature shear testing. The assembled test specimen was then conditioned in an oven set to 70 °C for 30 minutes prior to hanging a weight. Once the 30 minutes was up, a 1 kg weight was applied to the sample by hanging it on the loop below the sample using an aluminum hook with a flat bar. Time for the adhesive to fail was noted, unless the time reached 10,000 minutes, then the test was terminated.

[0225] Adhesive Transfer Tape (Adhesive between liners) Sample PreparationMonomer-polymer mixtures were made by combining the raw materials listed in Table 2 within a glass jar and partially polymerizing the mixture by exposing the jar to 0.3 mW / cm2UV-LED irradiation (365 nm) until the mixture had a higher viscosity (about 1000 cP). Curable compositions were made by combining the components listed in Table 3. The designated monomer-polymer mixture, i.e. MP-X was used at 100 wt.% or 100 parts and the rest of the components listed in Table 3 w ere added at the amountslisted by calculating the parts per hundred (ppr or phr) based on the amount of the MP-X. For example. 5 g of BMI PF6, 0.1 g of HDDMA, and 0.5 g of Irgacure 651 was added to 100 g of MP-1 in E1. Then each curable composition (El through E70, CE1 through CE25) was coated between two release liners (RF12N and RF02N). The samples were then cured under 365 nm UV-LED lights with a total dosage of 3.1 J / cm2as measured with a radiometer equipped with a high-power sensing head (available under the trade designation “POWER PUCK II” from EIT Incorporated, Sterling, VA), resulting in transfer tapes, which had an adhesive layer thickness of 2, 4, 8, or 14 mil (50, 100. 200, 350 qm) as listed in Table 3.

[0226] Multi-layer Sample (ML-E1, ML-E2, ML-E3, ML-E4, ML-E5, ML-E6, ML-E7, ML-E8) Tape Sample Preparation

[0227] ML -El was made as follows: adhesive transfer tape, E50 was cut into a 1” by 3” rectangle. The RF02N release liner (SKC Haas Display Films LLC, Seoul KR) of E50 transfer tape was first removed and the exposed tacky adhesive surface was laminated / rolled by hand onto to 3” wide piece of 2 mil plasma primed PET backing using a 6 inch (15 cm) rubberized hand roller, (Polymag Tck, NY) ensuring no air bubbles were trapped between the adhesive and the PET backing. The remaining RF12N liner of the E50 adhesive transfer tape / PET backing was then removed to expose the other side of the tacky E50 adhesive. Then a 1” by 3” rectangle of the conductive primer-1 on RF12N w as placed primer side down onto tire exposed tacky E50 adhesive side and laminated / rolled by hand using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek, NY) ensuring no air bubbles were trapped between the adhesive and the conductive primer- 1. The RF12N liner of the conductive primer- 1 construction was then removed, transferring the conductive primer layer (without the RF12N liner) onto the E50 adhesive layer. Then one more piece of adhesive transfer tape, E50 was cut into a 1” by 2.5” rectangle. The RF02N release liner (SKC Haas Display Films LLC, Seoul KR) of the E50 transfer tape was first removed and the exposed tacky adhesive surface was laminated / rolled by hand onto to the conductive primer side of the backing / E5() transfer tape / primer construction using a 6 inch (15 cm) rubberized hand roller. (Polymag Tek, NY) ensuring no air bubbles were trapped between the E50 adhesive and the conductive primer, also ensuring that 0.5” of the conductive primer- 1 was left uncovered by E50 to enable electrical contact to be made with it when doing electro debonding in peel mode. The RF12N liner of the construction was then removed to adhere the multi-layer tape construction with plasma primed backing to stainless steel to perform peel adhesion testing with and without electrical debonding, as described in the test methods section.ML-E2 was made in a similar manner as described for ML-E1, except instead of the E50 transfer tape being used it was E49 transfer tape laminated either side of conductive foam-1, also ensuring that 0.5” of the conductive foam-1 w as left uncovered by E49 to enable electrical contact to be made w ith it when doing electro debonding in peel mode. ML-E4 through ML-E6 were made in the exactly the same w ay as ML-E1, except E51 w as used instead of E50 for ML-E4. For ML-E5 E52 was used instead of E50 and for ML-E6, E53 was used instead of E50.ML-E3 was made as follows. 3M 86415 VHB foam tape was cut into a 1” by 3” rectangle. The easy side release liner of the 3M 86415 transfer tape was first removed and the exposed tacky adhesive surface was laminated / rolled by hand onto to 3” wide piece of 2 mil plasma primed PET backing using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek. NY) ensuring no air bubbles were trapped between the adhesive and the PET backing. The tight release side liner of the 3M 86415 transfer tape / backing was then removed to expose the other side of the adhesive tape. Then a 1” by 3” rectangle of the conductive primer-1 on RF12N was placed primer side down onto the exposed tacky adhesive and laminated / rolled by hand using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek. NY) ensuring no air bubbles were trapped between the adhesive and the conductive primer-1. The RF12N liner of the conductive primer-1 construction was then removed, transferring the conductive primer layer onto the 3M 86415 adhesive layer. Then adhesive transfer tape, E49 was cut into a 1” by 2.5” rectangle and the RF02N release liner (SKC Haas Display Films LLC. Seoul KR) of the E49 transfer tape was first removed and the exposed tackj’ adhesive surface was laminated / rolled by hand onto to the primer side of the conductive primer-1 / 3M 86415 / plasma primed PET backing construction using a 6 inch (15 cm) rubberized hand roller, (Polymag Tek, NY) ensuring no air bubbles were trapped betw een the E49 adhesive and the conductive primer, also ensuring that 0.5” of the conductive primer- 1 was left uncovered by E49 to enable electrical contact to be made with it when doing electro debonding in peel mode. ML-E7 and ML-E8 were made in the exact same way as ML-E3, except 3M 4941 and 3M 4950 (respectively) were used instead of 3M 86415.Acid Monomer Free Curable CompositionsCurable compositions for samples CE26-CE29 and E71-E79 were made by combining the components listed in Table 3. The designated monomer-polymer mixture, i.e. MP-X was used at 100 wt.% or 100 parts and the rest of the components listed in Table 3 were added at the amounts listed by calculating the parts per hundred (ppr or phr) based on the amount of the MP-X. For example, 0.1 g of HDDMA and 0.2 g of Irgacure 651 was added to 100 g of MP-26 in E71. Then each curable composition was coated between two release liners (RF12N and RF02N). The samples w ere then cured under 365 run UV-LED lights with a total dosage of 3.1 J / cm2as measured with a radiometer equipped with a high-power sensing head (available under the trade designation “POWER PUCK II” from EIT Incorporated, Sterling, VA), resulting in transfer tapes, which had an adhesive layer thickness of 2 mil (50 pm) as listed in Table 3.Table 2. Monomer Polymer (MP-X) Compositions.Monomer Polymer Composition phr Alkyl acry late monomer First Second OptionalMP OtherNitrogen Nitrogen Ether Irg ID 2-EHA BA C18 Wt.% Wt.% Wt.% Polar Wt.% HDDMA Monomer Monomer Monomer 651 Wt.% Wt.% Wt.% MonomerType Type TypeMP-1 70 NNDMA 15 NVP 15 0.02 0.04 MP-2 35 NNDMA 15 NVP 15 2MOEA 35 0.02 0.025 MP-3 35 NNDMA 15 NVP 15 M(EO)2EA 35 0.02 0.025 MP-4 15 NNDMA 10 NVP 25 M1086 50 0 0.025 MP-5 30 20 NNDMA 10 NVP 20 M1086 30 0 0.025 MP-6 50 20 NNDMA 15 VMOX 15 0.02 0.025 MP-7 68 NNDMA 26 NVP 5 AA 1 0.02 0.025 MP-8 68 NNDMA 26 NVC 5 AA 1 0.02 0.025 MP-9 50 15 NNDMA 30 NVP 5 0.02 0.025 MP- 10 50 15 NNDMA 20 NVP 15 0.02 0.025 MP- 11 65 NNDMA 20 NVP 15 0.02 0.025 MP- 12 65 NNDEA 20 NVP 15 0.02 0.025 MP-13 50 15 NNDMA 25 NVP 10 0.02 0.025 MP-14 50 20 NNDMA 15 NVIM1D 15 0 0.025 MP- 15 50 20 ACMO 5 NVP 25 0 0.025 MP- 16 50 20 ACM 5 NVP 25 0 0.025 MP- 17 45 20 5 NNDMA 15 NVP 15 0 0.0251MP- 18 46 16 NNDMA 28 NVC 10 AA 0.02 0.04(phr)MP-19 70 NNDMA 30 0.02 0.025 MP-20 90 AA 10 0 0.025 MP-21 70 NVP 10 HEA 20 0 0.025 MP-22 70 TOACM 30 0 0.025 MP-23 80 NVP 20 0 0.025 MP-24 70 NVP 30 0 0.025 MP-25 70 VMOX 30 0 0.025 MP-26 80 NVP 20 0 0.025 MP-27 50 15 NNDMA 15 NVP 20 0.02 0.025 MP-28 50 15 NNDMA 10 NVP 25 0.02 0.025 MP-29 50 15 NNDMA 5 NVP 30 0.02 0.025 MP-30 45 15 NNDMA 30 NVC 10 0.02 0.04 MP-31 95 AA 5 0.025 MP-32 100 0.025 MP-33 80 HBA 20 0.025Table 3. Adhesive compositions.Additives to MP-X(Amounts in parts per hundred resin, or phr, relative to 100 parts of MP-X) Adhesive Monomer Wt.% in parentheses is relative to polymerizable components only ID Thickness Polymer(pm) ID Additive- 1 Additive-2 Additive-3HDDMA IRG 651 Phr Phr PhrType (Phr) (Phr)(wt.%) Type (wt.%) Type (wt.%)El 200 BMI PF6 5 0.1 0.5 E2 100 TES TFSI 5 0.1 0.5TMAEAE3 10 (8.3) PEGA 10 (8.3) 0.1 0.5FSI MP-1TMAEA PEM 63E4 200 10 (8.3) 10 (8.3) 0.05 0.5FSI HDE5 BMI PF6 5 AA i (i.o) 0.1 0.5 E6 BMI PF6 5 PEGA 5 (4.8) B30HH 15 0.125 0.5 E7 BMI PF6 5 0.1 0.5MP-2 TMAEAE8 10 (9.1) 0.1 0.5FSI100 TMAEAE9 5 (4.8) 0.1 0.5MP-3 FSITMAEAE10 10 (9.1) 0.1 0.5FSIEll BMI PF6 5 0.1 0.5MP-4 TMAEAE12 10 (8.7) PEGA 0.1 0.5FSI 5 (4.3)TMAEAE13 15 (11.5) PEGA 15 (11.5) 0.1 0.5200 FSITMAEA 1M16K- E14 MP-5 15 (11.5) PEGA 15 (11.5) 20 0.1 0.5FSI MAS TMAEA MX- E15 15 (11.5) PEGA 15 (11.5) 15 0.1 0.5FSI 80H3wTE16 MP-6 BMI PF6 5 0.05 0.5E17 BMI PF6 5 PEGA 5 (4.8) 0.05 0.5 TMAEAE18 10 (8.0) PEGA 15 (12.0) 0.05 0.5FSIE19 MP-7 BMI PF6 5 PEGA 5 (4.8) EMS 5 0.1 0.5 E20 MP-8 BMI PF6 5 PEGA 5 (4.8) EMS 5 0.1 0.5 E21 BMI PF6 5 0.1 0.5MP-9E22 BMI PF6 5 PEGA 5 (4.8) 0.1 0.5 E23 BMI PF6 5 0.1 0.5MP- 10E24 BMI PF6 5 PEGA 5 (4.8) 0.1 0.5 E25 BMI PF6 5 0.1 0.5MP- 11E26 BMI PF6 5 PEGA 5 (4.8) 0.1 0.5 E27 MP-12 BMI PF6 5 0.1 0.5TMAEAE28 MP-13 15 (11.1) PEGA 20 (14.8) sK15 20 0.075 0.2FSIE29 BMI FSI 3 Li FSI 3 0.1 0.5 E30 BMI PF6 5 BZT 0.5 AA 0.1 0.5MP-4 1 (1.0)E31 TMAEA 10 (8.3) ACAC- F 5 (4.2) PEGASI MA 5 (4.2) 0.1 0.5 E32 BMI PF6 5 0.1 0.5 E33 BMI PF6 5 AA 1 (i.o 0.1 0.5MP- 14 )TMAEAE34 10 (8.3) PEGA 10 (8.3) 0.1 0.5FSIE35 BMI PF6 5 0.1 0.2 E36 BMI PF6 5 CB 1 0.1 0.2 E37 BMI PF6 5 EF2806 2 0.1 0.2MP- 15E38 BMI PF6 5 HECLA 10 (9.1) 0.1 0.2HDMAEE39 10 (8.3) PEGA 10 (8.3) 0.1 0.2A FSIE40 MP- 16 BMI PF6 5 0.1 0.2 E41 TMAEA15 (11.1) PEGA 20 (14.8) OP 930 20 0.1 0.2 MP-13 FSIE42 350 BMI PF6 5 OP 930 20 0.1 0.2E43 BMI PF6 5 20 AA 1 (1.0) 0.1 0.2 E44 50 MP- 17 BMI PF6 2 0.1 0.2TMAEAE45 15 (11.1) PEGA 20 (14.8) KVA 64 5 0.075 0.2FSI200TMAEAE46 15 (11.1) PEGA 20 (14.8) LA4285 10 0.075 0.2FSI TMAEAE47 350 15 (11.1) PEGA 20 (14.8) S4630 10 0.10 0.2FSIE48 200 SPA BMI 20 (14.3) PEGA 20 (14.3) S4630 10 0.10 0.2 E49 50 MP- 13 TMAEA 15 (11.1) PEGA 20 (14.8) S4630 10 0.10 0.2FSI TMAEAE50 15 (11.1) PEGA 20 (14.8) S4630 10 0.10 0.2FSIE51 SPA OMI 20 (16.0) PEGA 5 (4.0) 0.075 0.2 E52 SPA OMI 10 (7.7) TMAEA 10 (7.7) PEGA 100.075 0.2 FSI (7.7)200 SPACME53 10 (8.3) PEGA 10 (8.3) 0.075 0.2BMI IEAE54 HE 15 (10.0) 15MI PEGA 20 (13.3) XT 100 (10.0) 0.1 0.5 PF6E55 BMI PF6 10 PEGA 5 (4.8) 0.1 0.2 E56 MP-27 BMI PF6 12.5 PEGA 5 (4.8) 0.1 0.2 E57 BMI PF6 12.5 PEGA 5 (4.8) 0.05 0.2 E58 BMI PF6 12.5 PEGA 5 (4.8) 0.05 0.4 E59 BMI PF6 10 PEGA 0.1 0.275 5 (4.8)E60 MP-28 BMI PF6 12.5 PEGA 5 (4.8) 0.1 0.2 E61 BMI PF6 12.5 PEGA 5 (4.8) 0.05 0.2 E62 BMI PF6 10 PEGA 5 (4.8) 0.1 0.2 E63 MP-29 BMI PF6 12.5 PEGA 5 (4.8) 0.1 0.2 E64 BMI PF6 12.5 PEGA 5 (4.8) 0.05 0.2E65 50 MP-30 BMI PF6 7.5 PEGA 10 (9.0) 0.1 0.2E66 BMI PF6 9 PEGA 10 (9.0) 0.1 0.2 E67 BMI PF6 10.5 PEGA 10 (9.0) 0.1 0.2 E68 BMI PF6 13 PEGA 13 (11.5) 0.1 0.2 E69 BMI PF6 16 PEGA 13 (11.5) 0.1 0.2 E70 BMI PF6 13 PEGA 6 (5.7) 0.07 0.2 CE1 0.1 0.5MP- 19CE2 BMI PF6 5 0.1 0.5 CE3 0.1 0.5 CE4 BMI PF6 5 AA 2 (2.0) 0.1 0.5MP-1CE5 BMI PF6 5 AA 0.1 0.5100 5 (4.8)CE6 BMI PF6 5 AA 10 (9.1) 0.1 0.5 CE7 MP-2 0.1 0.5 CE8 MP-6 0.1 0.5 CE9 BMI FSI 5 0.1 0.5MP-20CE10 TES TFSI 5 0.1 0.5 CE11 MP-9 0.1 0.5 CE12 MP- 10 0.1 0.5 CE13 MP- 11 0.1 0.5 CE14 MP- 12 0.1 0.5 CE15 0.1 0.5 CE16 MP -21 BMI PF6 5 0.1 0.5 CE17 BMI PF6 5 PEGA 5 (4.8) 0.1 0.5 CE18 0.1 0.5MP-22CE19 200 BMI PF6 5 0.1 0.5 CE20 TMAEA5 (4.8) PEGA 10 (8.7) XT 100 10 0.1 0.5 TFSI MP-23*CE21 TMAEA 10 (8.3) PEGA 10 (8.3) XT 100 10 0.1 0.5TFSI CE22 MP-19 0.125 0.5 CE23 MP-24 0.125 0.5CE24 MP-25 0.125 0.5CE25 MP-22 0.125 0.5 CE26 MP-31 BMI TFSI 5 0.1 0.2 TBMA CE27 MP-31 5 0.1 0.2 FSI TBMP CE28 MP-31 5 0.1 0.2 FSI CE29 MP-31 TES TFSI 5 0.1 0.2 E71 MP-26 BMI FSI 5 0.1 0.2 E72 MP-26 BMI TFSI 5 0.1 0.2 E73 50 MP-26 TBMA 5 0.1 0.2 FSI TBMPE74 MP-26 5 0.1 0.2 FSIE75 MP-26 TES TFSI 5 0.1 0.2 E76 MP-32 BMI FSI 5 0.15 0.2 E77 MP-32 BMI TFSI 5 0.15 0.2 E78 MP-33 BMI FSI 5 0.05 0.2E79 MP-33 BMI TFSI 5 0.05 0.2 * Pentaerythritol tetrakis(3 -mercaptopropionate) (PTMP) was added as a chain transfer agent (CT A) at 0.2 phr loading to CE20 and CE21 to try to limit the undesirable exothemric effect from the amount of NVP in MP-23, but this was un-successful and resulted in thermally induced shrinkage of the RF12N and RF02N PET liners.Table 4. Test results for 180 degree peel adhesion to stainless steel (SS) and tensile pushout from SS to SS with and without electro debonding. Failure modes for peel adhesion and tensile pushout testing are adhesive (i.e. clean removal from SS substrate), unless stated otherwise.180 degreePeel Tensile Push Out, SS to SS Adhesion toExampleSS Initial % Reduction (12” / min, Peak Stress After 50 V N / mm) (MPa) for 1 min / 60sEl 1.14 0.86 85% E2 0.79 0.78 55% E3 1.60 0.98 78% E4 0.91 0.91 71% E5 1.28 0.93 50% E6 0.67 1.46 65% E7 0.93 0.43 73% E8 2.18 1.36 53% E9 0.71 0.48 94% E10 1.21 0.50 58% Ell 0.73 0.68 90% E12 0.84 0.97 74% E13 1.06 0.57 73% E14 1.12 0.80 59% E15 0.94 0.87 68% E16 1.14 1.17 61% E17 1.03 1.10 81% E18 1.12 1.14 67% E19 N / A 0.56 67% E20 N / A 0.48 54% E21 1.11 1.15 68% E22 0.83 0.94 74% E23 1.60 1.17 71% E24 1.10 0.83 87% E25 1.12 1.25 65% E26 1.15 1.03 80% E27 0.88 0.62 98% E28 1.29 0.64 70% E29 0.36 0.83 100% E30 0.58 0.58 88% E31 0.72 0.72 74% E32 1.22 1.21 62% E33 1.57 1.72 60% E34 1.24 1.14 61% E35 1.00 0.91 61% E36 0.88 1.06 67% E37 0.85 0.86 53% E38 0.61 0.66 87%E39 0.99 1.00 54%E40 1.60 2.30 70% E41 1.21 1.06 64% E42 1.32 1.05 78% E43 1.34 1.36 69% E44 0.56 0.22 64% E45 1.02 1.42 80% E46 1.07 1.66 77% E47 1.75 0.80 67% E48 0.76 0.49 81% E49 0.90 1.16 82% E50 1.01 1.16 61% E51 0.78 0.80 89% E52 0.85 1.34 86% E53 0.78 1.06 68% E54 0.65 0.94 54% CE1 1.00 0.59 21% CE2 0.80 0.57 29% CE3 0.82 0.47 0% CE4 1.15 1.20 0% CE5 1.47 2.44 0% CE6 0.23 1.25 0% CE7 0.93 0.31 0% CE8 0.80 0.62 0% CE9 0.74 0.77 0% CE10 0.82 0.78 0% CE11 1.20 1.03 0% CE12 1.02 1.16 0% CE13 1.11 1.29 0% CE14 0.96 0.69 2% CE15 1.02 0.57 0% CE16 0.88 0.44 7% CE17 0.79 0.43 2% CE18 1.64 1.22 4% CE19 1.44 1.46 12% CE20 0.73 0.81 22% (5 min / 300s)CE21 0.75 0.72 33% (5 min / 300s)Table 5. Test results for 180 degree peel adhesion to stainless steel (SS) and tensile pushout from SS to SS with and without electro debonding. Failure modes for peel adhesion and tensile pushout testing are adhesive (i.e. clean removal from SS substrate), unless stated otherwise.Peel Tensile Pushout, SS to SSAdhesion Static1 day dwell at CTH Shear to SSExample (12” / min, SS to 50V, 1 min 9V, 1 minN / mm) Initial SS1 day, Stress Final Final 1 kg% %CTH (MPa) Stress 70 °Reduc Stress C tion Reduction(MPa) (MPa)E55 0.69 0.88 0.14 84% N / A N / A 10,000 E56 0.75 1.01 0.02 98% 0.13 87% 10,000 E57 0.78 1.23 0.09 88% 0.19 84% 4,250 E58 0.81 1.69 0.09 89% 0.24 85% 1,000 E59 0.77 1.20 0.06 95% 0.10 92% 10,000 E60 0.78 1.01 0.09 91% 0.05 95% 10,000 E61 0.81 1.15 0.13 84% 0.27 76% 10,000 E62 0.71 1.36 0.17 87% N / A N / A 10,000 E63 0.72 1.25 0.09 93% 0.20 84% 10,000E64 0.81 1.03 0.14 82% 0.44 57% 10,000 Table 6. Test results for 180 degree peel adhesion to stainless steel (SS) with and without electro debonding. Failure modes for peel adhesion and tensile pushout testing are adhesive (i.e. clean removal from SS substrate), unless stated otherwise.Peel Adhesion to SS(12” / min, N / mm)30 min dwell at CTHExample 10 V / 5 s 10 V / 10 s 10 V / 20 s InitialPeel Final Final Final Force % % %Peel Reduction Peel Reduction Peel Reduction Force Force ForceE65 0.68 0.15 78% 0.15 78% 0.06 91% E66 0.71 0.14 80% 0.08 88% 0.03 96% E67 0.64 0.18 72% 0.06 91% 0.01 98% E68 0.70 0.10 86% 0.02 97% 0.01 99% E69 0.69 0.04 94% 0.00 100% 0.01 99%E70 0.85 N / A N / A 0.01 99% 0.03 97%Table 7. High temperature (70 °C) static shear to stainless steel (SS) test results.Static ShearExample to SS1 Kg at 70 °CE4 10,000+Ell 10,000+E12 10,000+E28 10,000+E30 3429E31 6030E32 4325E33 4181E34 4846E35 10,000+E36 10,000+E37 10,000+E38 8132E39 10,000+E40 10,000+E41 10,000+E42 10,000+E43 10,000+E45 10,000+E46 2653CE18 1CE19 1CE22 450CE23 10,000+CE24 10,000+CE25 67Table 8. Composition of ABC multi-layer adhesive tape examples with conductive core.ABC Skin, A Conductive Core, B Skin, C ABCMulti-layerMulti-layer Thickness Thickness Thickness Total Thickness Composition Composition Composition Example (pm) (pm) (pm)(pm)ML-E1 407 E50 200 Conductive Primer- 1 7 E50 200 ML-E2 400 E49 50 Conductive Foam-1 300 E49 50 ML-E3 202 E49 50 Conductive Primer- 1 7 3M 86415 150 ML-E4 407 E51 200 Conductive Primer- 1 7 E51 200 ML-E5 407 E52 200 Conductive Primer- 1 7 E52 200 ML-E6 407 E53 200 Conductive Primer- 1 7 E53 200 ML-E7 1,182 E49 50 Conductive Primer- 1 7 3M 4941 1,125 ML-E8 1,182 E49 50 Conductive Primer- 1 7 3M 4950 1,125Table 9. Test results for 180-degree peel adhesion to SS with and without electro debonding. Failure modes are adhesive (i.e. clean removal from SS substrate), unless stated otherwise.Peel Adhesion to SS Peel AdhesionMulti-layer (12” / min), after 1 min at 50 Peel reduction after 1 min at 50 Example 20 min dwell CTH V(N / mm) (N / mm) VML-E1 1.47 (adhesive) 0.03 98%ML-E2 0.34 (foam split) 0.01 97%ML-E3 1.06 (foam split) 0.03 97%ML-E4 1.41 0.55 (1 day) 61% (5 min) ML-E5 1.05 0.33 69%ML-E6 1.32 0.05 96%ML-E7 2.68 0.02 99%ML-E8 2.99 0.01 99%Table 10. Test results for 180-degree peel adhesion to SS with and without electro debonding. There was a delay in testing after electro debonding of 60 seconds. Failure modes are adhesive (i.e. clean removal from SS substrate)Peel ElectricallyAdhesion Debonded Peelto SS AdhesionExample 30 min (12” / min, N / cm)CTH(12” / min, 10V for 30 sec,N / cm) 60 second delayCE26 13.1 8.1CE27 12.7 9.1CE28 6.0 5.8CE29 12.7 5.8E71 5.7 0.1E72 5.8 0.1E73 6.3 0.3E74 5.9 0.1E75 6.4 0.1E76 2.3 0.00E77 1.9 0.07E78 0.7 0.01E79 0.7 0.05

[0228] Other modifications and variations to the present disclosure may be practiced by those of ordinary skill in the art. without departing from the spirit and scope of the present disclosure, which is more particularly set forth in the appended claims. It is understood that aspects of thevarious embodiments may be interchanged in whole or part or combined with other aspects of the various embodiments. All cited references, patents, or patent applications in the above application for letters patent are herein incorporated by reference in their entirety in a consistent manner. In the event of inconsistencies or contradictions between portions of the incorporated references and this application, the information in the preceding description shall control. The preceding description, given in order to enable one of ordinary skill in the art to practice the claimed disclosure, is not to be construed as limiting the scope of the disclosure, which is defined by the claims and all equivalents thereto.

Claims

1. What is claimed is:

1. A polymerizable composition comprising:a) a C 1 -C 18 alkyl (meth)acry late ester monomer;b) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components;c) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components; and d) an ionic liquid,with the proviso that the ionic liquid may comprise functionality of the first nitrogencontaining monomer to provide both component b) and component d) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component c) and component d).

2. The polymerizable composition of claim 1, wherein the combined amount of components b) and c) ranges from 10 wt.% to 45 wt.%, based on a total weight of polymerizable components.

3. The polymerizable composition of claim 1 or claim 2, wherein the second nitrogencontaining monomer is present in an amount of 5 wt.% to 25 wt.%, based on a total weight of polymerizable components.

4. The polymerizable composition of any of claims 1 to 3, wherein a weight ratio of component b) to component c) is between 1 and 6.

5. The polymerizable composition of any of claims 1 to 4, wherein the first nitrogencontaining monomer comprises at least one of N. N-dimethylacrylamide (NNDMA), N. N-diethylacrylamide (NNDEA), N, N-dimethylaminopropyl acrylamide (DMAPACM), N-tert-octyl acrylamide (NTOA), N -octyl acrylamide (NOA), acrylamide (Acm), 4-acryloylmorpholine (ACMO), N-isopropylacrylamide, (NIPAM), N-hydroxy ethyl acrylamide (NHEA), N-(isobutoxymethyl)acrylamide (NIBMA), N-tert-butylacrylamide (NTBA), N-(3-methoxypropyl)acrylamide (NMPA), or sulfopropyl acrylamide N-butyl-N'-methyl imidazolium.

6. The polymerizable composition of any of claims 1 to 5, further comprising an ethoxy group-containing (meth)acrylate monomer in an amount of 5 wt.% to 50 wt.%, based on a total weight of polymerizable components.

7. The polymerizable composition of any of claims 1 to 6. wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises a C8 acrylate in an amount of 30 wt.% or greater, based on a total weight of polymerizable components.

8. The polymerizable composition of any of claims 1 to 7, further comprising at least one additive selected from the group consisting of an adhesion promoter, a stabilization agent, a corrosion inhibitor, a conducting salt, and a polymer having a glass transition temperature of at least 40 degrees Celsius.

9. The polymerizable composition of any of claims 1 to 8, further comprising a filler comprising a plurality of hollow glass microspheres, a plurality of polymeric microparticles, a plurality of polymeric nanoparticles each comprising an interior region comprising a polymer having a glass transition temperature below room temperature and an outer shell comprising a polymer having a glass transition temperature of at least 0 °C, an organo-phosphinate, a plurality of alumina particles, a plurality of pre-expanded hollow polymeric microspheres, a plurality of conductive particles, or combinations thereof.

10. The polymerizable composition of any of claims 1 to 9, further comprising a carboxylic acid-containing (meth)acrylate monomer in an amount of less than 2 parts per hundred parts resin (phr) of the polymerizable composition.

11. The polymerizable composition of any of claims 1 to 10, further comprising a (meth)acrylate macromer comprising one or more of a polyethylene oxide) group, a polypropylene oxide) group, a poly(ethylene oxide-co-propylene oxide group, a poly(tetrahydrofuran) group; a poly(ester) group, or combinations thereof.

12. The polymerizable composition of any of claims 1 to 11, containing less than 0.1 wt.% of a hydroxyl-containing (meth)acrylate monomer, based on a total weight of polymerizable components.

13. The polymerizable composition of any of claims 1 to 12, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises at least one of 2-ethylhexyl acrylate, n-butyl acrylate, 2-methylbutyl aery late, n-hexyl acrylate, or 6-methylheptyl acrylate.

14. The polymerizable composition of any of claims 1 to 13, wherein the C1-C18 alkyl (meth)acrylate ester monomer is present in an amount of 15 wt.% to 90 wt.%, based on a total weight of polymerizable components.

15. The polymerizable composition of any of claims 1 to 14, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises a C6-C18 (meth)acrylate ester monomer present in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

16. The polymerizable composition of any of claims 1 to 15, wherein the second nitrogencontaining monomer comprises at least one of N-vinyl pyrrolidone, vinyl methyl oxazolidinone, or N-vinyl caprolactam, N-vinyl imidazole, N-vinyl carbazole, N-vinyl formamide, N-methyl-N-vinyl acetamide, N-vinyl piperidone. or N-vinyl-imidazolium bis(fluorosulfonyl)imide.

17. The polymerizable composition of any of claims 1 to 16, wherein the ionic liquid comprises a polymerizable ionic liquid that is present in an amount of 1 wt.% to 50 or 40 or 30 wt.%, based on a total weight of polymerizable components.

18. The polymerizable composition of any of claims 1 to 17, wherein the ionic liquid comprises a non-polymerizable ionic liquid that is present in an amount of 2 parts per hundred parts resin (phr) to 20 phr.

19. The polymerizable composition of any of claims 1 to 18, wherein the ionic liquid comprises at least one of a sulfate, a sulfonate, a carboxylate, a phosphate, a borate, a phenyl borate, an oxalato borate, a nitrate, an imide, a sulfidoimide, a dicyanamide, a tricyanomethanide, or a halide ion.

20. The polymerizable composition of any of claims 1 to 19, wherein the ionic liquid comprises at least one of an imidazolium. an ammonium, a pyridinium, a phosphonium, a sulfonium, or an iodonium ion.

21. The polymerizable composition of any of claims 1 to 20, further comprising a crosslinker.

22. An at least partially polymerized reaction product of the polymerizable composition of any of claims 1 to 21.

23. A pressure sensitive adhesive article comprising an adhesive composition comprising the at least partially polymerized reaction product of claim 22, wherein the adhesive composition is disposed on at least a portion of a substrate.

24. The adhesive article of claim 23, wherein the substrate is a liner comprising a release agent, a backing, or a carrier.

25. The adhesive article of claim 23 or claim 24, further comprising a second adhesive layer, wherein the substrate is a carrier and the substrate is disposed between the adhesive composition and the second adhesive layer.

26. The adhesive article of claim 24 or claim 25, wherein the carrier comprises a conductive material.

27. The adhesive article of any of claims 23 to 26, wherein the adhesive composition exhibits a tensile pushout strength of greater than 0.2 megaPascals (MPa), as determined by the Tensile Pushout Test Method.

28. The adhesive article of any of claims 23 to 27, wherein the adhesive composition exhibits a decrease in tensile pushout strength of at least 50% following subjection to 9 volts (V), 10 V, 20 V, 30 V, 40 V, or 50 V, for one minute, as determined by the Tensile Pushout Test Method.

29. The adhesive article of any of claims 23 to 28, wherein the adhesive composition exhibits a decrease in peel strength of at least 50% following subjection to 50 volts (V) for one minute, as determined by the Peel Adhesion Test Method.

30. The adhesive article of any of claims 23 to 28, wherein the adhesive composition exhibits a decrease in peel strength of at least 50% following subjection to 10 volts (V) for 5 seconds, 10 seconds, 20 seconds, 30 seconds, 45 seconds, or 60 seconds, as determined by the Peel Adhesion Test Method.

31. The adhesive article of any of claims 23 to 30, wherein the at least partially polymerized reaction product comprises a polymer that is a polymerized reaction product of at least components a), b), and c).

32. A polymerizable composition comprising an adhesive precursor and a polymerizable ionic liquid of Formula I and / or of Formula II:wherein in each of Formula I and Formula II, Ri is independently H or methyl, and R₂ and R₃ are each independently linear or branched alkyl groups and / or ethoxy groups.

33. A polymerizable composition comprising:a) a Cl -C 18 alkyl (meth)acrylate ester monomer; andb) an ionic liquid,with the proviso that the polymerizable composition is essentially free of a carboxylic acid-containing (meth)acrylate monomer.

34. The polymerizable composition of claim 33, further comprising:at least one nitrogen-containing monomer.

35. The polymerizable composition of claim 34, wherein the at least one nitrogen-containing monomer comprises:c) 5 weight percent (wt.%) to 30 wt.% of a first nitrogen-containing monomer that is an acrylamide monomer, based on a total weight of polymerizable components;d) 5 wt.% to 30 wt.% of a second nitrogen-containing monomer that has a nitrogen atom directly attached to a vinyl group, based on a total weight of polymerizable components, with the proviso that the ionic liquid may comprise functionality of the first nitrogen-containing monomer to provide both component b) and component c) and / or the ionic liquid may comprise functionality of the second nitrogen-containing monomer to provide both component b) and component d).

36. The polymerizable composition of any of claims 33 to 35, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises a C8 acrylate in an amount of 30 wt.% or greater, based on a total weight of polymerizable components.

37. The polymerizable composition of any of claims 33 to 36, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises at least one of iso-octyl acrylate, 2-ethylhexyl acrylate, n-butyl acrylate, 2-methylbutyl acrylate, methyl acrylate, n-hexyl acrylate, n-octyl acrylate, or 6-methylheptyl acrylate.

38. The polymerizable composition of any of claims 33 to 37, wherein the C1-C18 alkyl (meth)acrylate ester monomer is present in an amount of 15 wt.% to 98 wt.%, based on a total weight of polymerizable components.

39. The polymerizable composition of any of claims 33 to 38, wherein the C1-C18 alkyl (meth)acrylate ester monomer comprises a C5-C18 (meth)acrylate ester monomer present in an amount of 30 wt.% to 90 wt.%, based on a total weight of polymerizable components.

40. The polymerizable composition of any of claims 33 to 39, wherein the ionic liquid comprises a polymerizable ionic liquid that is present in an amount of 1 wt.% to 50 wt.%, based on a total weight of polymerizable components.

41. The polymerizable composition of any of claims 33 to 40, wherein the ionic liquid comprises a non-polymerizable ionic liquid that is present in an amount of 2 parts per hundred parts resin (phr) to 20 phr.

42. The polymerizable composition of any of claims 33 to 41. wherein the ionic liquid comprises at least one of a sulfate, a sulfonate, a carboxylate, a phosphate, a borate, a phenyl borate, an oxalato borate, a nitrate, an imide, a sulfidoimide, a dicyanamide, a tricyanomethanide, or a halide ion.

43. The polymerizable composition of any of claims 33 to 42, wherein the ionic liquid comprises at least one of an imidazolium, an ammonium, a pyridinium, a phosphonium, a sulfonium, or an iodonium ion.

44. The polymerizable composition of any of claims 33 to 43, wherein the polymerizable composition is substantially free of solvent.

45. The polymerizable composition of any of claims 33 to 44. further comprising a poly ether macromer.

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