Articles containing adhesive compositions that exhibit on-demand peel behavior

Abstract

An article comprising a first component having a first conductive surface and a second component having a second surface. An adhesive composition comprising a cured polymerizable ionic liquid is disposed between the first conductive surface and the second surface, bonding the first component to the second component. The polymerizable ionic liquid comprises an acid functional monomer and a conjugate acid of an imidazole compound. The effort required to separate the first component from the second component, as measured by the work of adhesion per surface area, is reduced by applying a DC potential across the adhesive composition.

Description

[Technical field]

[0001] The present invention relates generally to articles containing two or more components joined together by an adhesive that exhibits on-demand peel behavior, and more particularly to articles that can be separated into two or more components by applying an electric potential to the adhesive. [Background technology]

[0002] Adhesives, including pressure sensitive adhesives (PSAs), are commonly used to bond parts to assembled articles in a variety of industries, including the electronics, automotive, aerospace, abrasive, medical device, and packaging industries. The bond strength of the adhesive between components in an article is important to achieve the desired performance characteristics for a particular application. In many applications, the adhesive must exhibit high peel strength to prevent separation or delamination of the components during use. For example, adhesives may be used in the automotive industry to bond trim to the sides of a car or truck. In other applications, the adhesive must be reworkable or repositionable. Typically, PSAs adhere more strongly to one component than to another, thus allowing for repositioning or replacement of the component to which the adhesive adheres more strongly. For example, PSAs may be used to bond protective covers to electronic devices such as cell phones, personal computers, or computer tablets. Due to the high cost of the article and the relatively low cost of the protective cover, it may be desirable to remove (peel off) the cover to repair the article, modify the article, reposition the backing on the article, or recycle the bonded article. Summary of the Invention

[0003] There is a need for an article containing an adhesive composition that allows for control of the timing of release and for affecting the surface to which the adhesive releases. The present disclosure provides an article including two or more components bonded together by an adhesive composition that exhibits on-demand peel behavior upon application of a direct current (DC) potential, and a method for separating the components. The surface to which the adhesive composition releases can be affected by the direction of the potential across the adhesive composition. The articles and methods described herein can be used, for example, in advanced manufacturing (e.g., to grip a part, transport the part to another location, and release the part on demand), device maintenance (e.g., to peel an adhesively secured access panel), and / or recycling for economic or environmental benefits (e.g., to separate components that require different recycling processes).

[0004] In a first embodiment, the present disclosure provides a method for manufacturing a semiconductor device comprising: a first component having a first conductive surface; a second component having a second surface; and an adhesive composition disposed between the first conductive surface and the second surface, the adhesive composition comprising a cured polymerizable ionic liquid; an adhesive composition bonds the first component to the second component; the effort required to separate a first component from a second component, as measured by the work of adhesion per surface area, is reduced by applying a DC potential across the adhesive composition; The polymerizable ionic liquid is A polymerizable anion and an imidazole compound of formula I [ka] (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R 1 is H or C 1 ~C 25 is an alkyl group, R 2 is H or -CO-X1 -R 5 and R 5 is H or C 1 -C 25 is an alkyl group, and X 1 is -O- or -NR 6 - and R 6 is H or C 1 -C 6 is alkyl, R 3 is H or CH 3 is preferably H, R 8 is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R 1 and R 2 is H) and a cation corresponding to the conjugate acid of

[0005] In another embodiment, the present disclosure provides a method of separating components in an article, the method comprising applying a DC potential across an adhesive composition to separate a first component from a second component.

[0006] As used herein, the term "adhesive composition" refers to an adhesive or composite (e.g., single- or double-sided tape) that includes a cured polymerizable ionic liquid that exhibits on-demand peel behavior when exposed to a DC potential.

[0007] As used herein, the term "polymerizable ionic liquid" refers to A polymerizable anion and an imidazole compound of formula I [ka] (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R 1 is H or C 1 ~C 25is an alkyl group, R 2 is H or -CO-X 1 -R 5 and R 5 is H or C 1 ~C 25 is an alkyl group, and X 1 is -O- or -NR 6 - and R 6 is H or C 1 ~C 6 is alkyl, R 3 is H or CH 3 is preferably H, R 8 is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, and w is 0, 1, 2 or 3. However, when Z contains a nitrile or azlactone functional group, R 1 and R 2 is H) and a cation corresponding to the conjugate acid of

[0008] The polymerizable ionic liquid may optionally include one or more additional components blended therewith.

[0009] As used herein, the term "on-demand peel" refers to the ability to reduce the strength of an adhesive bond at will in order to facilitate separation (i.e., peeling) of adhesively bonded components.

[0010] As used herein, the term "pressure sensitive adhesive" or "PSA" is defined as having the following properties: (1) aggressive and persistent tack, (2) adhesion with no more than finger pressure, (3) sufficient ability to attach to a substrate, and (4) sufficient cohesion to be cleanly removable from the substrate. Materials that have been found to perform well as PSAs include polymers designed and formulated to exhibit the necessary viscoelastic properties that provide the desired balance of tack, peel adhesion, and shear retention. PSAs are typically characterized as being tacky at room temperature. PSAs are adhesives that meet the Dahlquist criteria for tack, which is a shear storage modulus typically greater than 3×10 when measured at 25° C. and 1 Hertz (6.28 radians / sec). 5 Pa (300 kPa) or less. PSAs typically exhibit adhesive, cohesive, compliant, and elastic properties at room temperature.

[0011] As used herein, the terms "conductive" and "electrically conductive" are used interchangeably.

[0012] As used herein, the terms "negative electrode" and "negative adhesive interface" are used interchangeably, and the terms "positive electrode" and "positive adhesive interface" are used interchangeably.

[0013] As used herein, the term "polymerizable" refers to compounds, also referred to as "monomers," that are polymerizable and / or crosslinkable as a result of thermal, redox, or photolytic initiation. Such compounds have at least one α,β-unsaturated site. In some embodiments, monomers having one or more α,β-unsaturated sites are referred to as "crosslinkers," although it will be understood that the term "monomer" includes compounds having one or more such sites, as appropriate for the context.

[0014] As used herein, the terms "substantial" or "substantially" refer to relatively minor variations or aberrations from a stated property, value, range of values, content, formula, etc., and do not exclude the presence of additional materials, broader ranges of values, etc. that do not materially affect the desired properties of a given composition, article, product, or method.

[0015] As used herein, the term "comprising" and variations thereof do not have a limiting meaning when these terms appear in the specification and claims. Such terms are understood to imply the inclusion of the described step or element, or group of steps or elements, but not the exclusion of any other step or element, or group of steps or elements. "Consisting of" means to include and be limited to everything before the phrase "consisting of". Thus, the phrase "consisting of" indicates that the recited elements are necessary or mandatory, and that no other elements may be present. "Consisting essentially of" means to include any elements listed after the phrase, and any elements limited to other elements that do not interfere with or contribute to the activity or action specified in this disclosure with respect to those recited elements. Thus, the phrase "consisting essentially of" indicates that the recited elements are necessary or mandatory, but that other elements are optional and may or may not be present depending on whether they substantially affect the activity or action of the recited elements.

[0016] In this application, terms such as "a," "an," and "the" are not intended to refer to only a singular entity, but include general classes, specific examples of which may be used for illustration. The terms "a," "an," and "the" are used interchangeably with the phrases "at least one" and "one or more." The phrases "at least one of" and "including at least one of" following a list refer to any one of the items in the list, as well as any combination of two or more items in the list.

[0017] As used herein, the term "or" is generally used in its ordinary sense, including "and / or," unless the content specifically dictates otherwise. The term "and / or" refers to one or all of the listed elements or a combination of any two or more of the listed elements.

[0018] Also, all numbers herein are deemed to be modified by the term "about," and in certain embodiments, by the term "exactly." As used herein, in the context of a measured quantity, the term "about" refers to the variation in the measured quantity as would be expected by one of ordinary skill in the art making the measurement and exercising a level of care commensurate with the purpose of the measurement and the precision of the measuring device used. As used herein, a "up to" number (e.g., up to 50) is inclusive of that number (e.g., 50).

[0019] Also herein, the recitations of numerical ranges by endpoints include all numbers subsumed within that range, as well as the endpoints thereof (eg, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, etc.).

[0020] References throughout this specification to "several embodiments" mean that a particular feature, configuration, composition, or characteristic described in connection with an embodiment is included in at least one embodiment of the disclosure. Thus, the appearances of such phrases in various places throughout this specification do not necessarily refer to the same embodiment of the disclosure. Furthermore, the particular features, configurations, compositions, or characteristics may be combined in any suitable manner in one or more embodiments.

[0021] The words "preferred" and "preferably" refer to embodiments of the present disclosure that may provide certain benefits, under particular circumstances, although other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the present disclosure.

[0022] The above summary of the present disclosure is not intended to describe each disclosed embodiment or every implementation of the present disclosure. The following description more particularly illustrates exemplary embodiments. [Brief description of the drawings]

[0023] [Figure 1A] 1 is a schematic side view of one exemplary article of the present application. [Figure 1B] FIG. 1B is a schematic side view of a variation of the article of FIG. 1A. [Figure 1C] FIG. 1B is a schematic side view of another variation of the article of FIG. 1A. [Figure 2A] FIG. 2 is a schematic side view of another exemplary article of the present application. [Figure 2B] FIG. 2B is a schematic side view of a variation of the article of FIG. 2A. [Diagram 3] 1 is a plot of tensile force (Newtons) (y-axis) versus distance (millimeters) (x-axis) between two 8 mm stainless steel plates separated at a rate of 0.01 mm / sec for Example E4. [Figure 4] FIG. 1 is a contour surface plot of adhesion work per unit surface area (indicated by shading on scale) from tensile adhesion testing of Example E2 as a function of applied DC voltage (y-axis) and duration the voltage was applied before the plates were separated (x-axis).

[0024] When referring to the figures, like reference numbers when not multiples of 100 (e.g., 12 and 112 or 30 and 130) refer to like elements. Unless otherwise indicated, all figures and drawings in this document are not to scale and are selected for the purpose of illustrating different embodiments of the present invention. In particular, the dimensions of the various components are described in illustrative terms only, and no relationship between the dimensions of the various components should be inferred from the drawings, unless otherwise indicated. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] In the following description of exemplary embodiments, reference is made to the accompanying drawings which form a part hereof, and in which specific embodiments are shown by way of illustration, It is to be understood that other embodiments may be utilized and structural changes may be made without departing from the scope of the present invention.

[0026] The articles of the present disclosure generally include a first component having a first conductive surface, a second component having a second surface, and an adhesive composition disposed between the first conductive surface and the second surface. The adhesive composition (described in more detail below) includes an adhesive comprising a cured polymerizable ionic liquid and exhibits on-demand peel behavior when exposed to a DC potential. For example, the effort to separate the first component from the second component, as measured by the work of adhesion per surface area according to Test Method 2, is reduced by applying a DC potential across the adhesive composition.

[0027] The shape and form of the article in this disclosure is not particularly limited. The article may be a finished product or a part that is incorporated or attached to another object. The article is typically composed of at least two components that can be adhesively bonded to each other, and the article may be in the form of a two-dimensional or three-dimensional body. Similarly, the shape and form of the components that make up the article are not particularly limited. The components may be a single element or a combination of elements, and the components may be in the form of a two-dimensional or three-dimensional body. In some embodiments, two or more components are interconnected, or even two different parts of the same material are interconnected (e.g., one end of a composite strip of material may be folded over to be adhered to the opposite end of the strip).

[0028] To facilitate the separation of components bonded together by the adhesive composition, a DC potential is applied across the adhesive composition prior to separation of the components. For example, a potential may be applied across two conductive components on either side of the adhesive composition, such that the surface of one component acts as a negative electrode (or negative adhesive interface) and the surface of the other component acts as a positive electrode (or positive adhesive interface). Alternatively, a potential may be applied across one conductive component and a conductive adhesive carrier of a double-sided tape, such that the surface of the conductive component or the conductive adhesive carrier acts as a negative adhesive interface and the other of the conductive component or the conductive adhesive carrier acts as a positive adhesive interface. The application of a DC current typically weakens the adhesive bond at the negative adhesive interface, thus reducing the amount of effort required to separate the components in the article. The location of the peel can be reversed by simply changing the polarity of the potential.

[0029] FIG. 1 shows an embodiment of an article of the present disclosure, comprising two conductive components bonded together by an adhesive composition. Referring to FIG. 1A, the article 10 comprises a first component 12 having a first conductive surface 14 and a second component 22 having a second conductive surface 24. The first and second components 12, 22 are each made of a conductive material. The nature of the conductive material is not particularly limited. In some embodiments, the first conductive surface 14 and the second conductive surface 24 are each selected from the group consisting of metals, mixed metals, alloys, metal oxides, composite metals, conductive plastics, conductive polymers, or combinations thereof. In some embodiments, the composition of the first conductive surface 14 is different from the composition of the second conductive surface 24. In other embodiments, the composition of the first and second conductive surfaces 14, 24 is the same.

[0030] The adhesive composition 30 bonds the first and second components 12, 22 together at the first conductive surface 14 and the second conductive surface 24. The adhesive composition exhibits on-demand peel behavior by applying a DC potential across the adhesive composition 30. In this particular embodiment, the first conductive surface 14 functions as a positive adhesive interface and the second conductive surface 24 functions as a negative adhesive interface. The application of a DC potential 40 across the adhesive composition 30 results in a weakening of the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 24), as measured, for example, according to the work of adhesion per surface area, thus making it easier to separate the second component 22 from the first component 12. Preferably, little or no adhesive residue remains on the second conductive surface 24 after separation. In some embodiments, less than 10%, less than 5%, or less than 1% (by weight) of the adhesive composition remains on the second component 22 after separation. In some preferred embodiments, no adhesive composition remains on the second component 22 after separation. In some embodiments, the adhesive composition may be reusable, allowing the first component 12 to be rejoined to the second component 22, or to be adhered to an entirely different component or article. If it is desired that the adhesive remain on the second component 22 after separation, the polarity of the DC potential can be reversed, thereby causing the first conductive surface 14 to act as a negative adhesive interface.

[0031] Conductive components include components made entirely from conductive materials, as shown in FIG. 1A, and components made from non-conductive materials coated with conductive materials, as shown in FIG. 1B. Referring to FIG. 1B, the first component 12 includes a first non-conductive material 16 and a first conductive coating 18 to provide a first conductive surface 14. Similarly, the second component 22 includes a second non-conductive material 26 and a second conductive coating 28 to provide a second conductive surface 24. Alternatively (not shown), one of the components can be made entirely from a conductive material and the other can be made from a non-conductive material coated with a conductive material. The conductive coating may only partially coat the component, as shown in FIG. 1B, or may completely coat the outer surface of the component. For the purposes of this disclosure, it is only necessary that the surface of the component that is in direct contact with the adhesive composition be coated sufficiently to weaken the adhesive bond at the negative adhesive interface when a DC potential is applied across the adhesive composition. In some embodiments, the coating is a solid layer. In other embodiments, the coating is pattern coated on the surface of the component. As mentioned above, the conductive material is not particularly limited and can include materials selected from the group consisting of metals, mixed metals, alloys, metal oxides, composite metals, conductive plastics, conductive polymers, or combinations thereof.

[0032] The adhesive composition 30 of FIG. 1B bonds the first and second components 12, 22 together. The first conductive surface 14 serves as the positive adhesive interface and the second conductive surface 24 serves as the negative adhesive interface. Application of a DC potential 40 across the adhesive composition 30 results in a weakening of the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 24), as measured, for example, according to the work of adhesion per surface area, thus making it easier to separate the second component 22 from the first component 12. If it is desired that the adhesive composition remain primarily on the second component, the polarity of the DC potential can be reversed, thereby causing the first conductive surface to serve as the negative adhesive interface.

[0033] The article of Figures 1A-B may further be adapted to bond and subsequently release non-conductive objects or elements using the adhesive composition, as shown in Figure 1C. The article of Figure 1C includes a conductive first component 12 having a first conductive surface 14 and a conductive second component 22 having a second conductive surface 24. The first and second components 12, 22 are bonded together by an adhesive composition 30. The first and second components may be made of conductive materials, although it should also be understood that the first and / or second components may be made of non-conductive materials and coated with a conductive material, as illustrated in Figure 1B. Figure 1C differs from Figures 1A-B in that a first outer adhesive 50 is added to the second side 19 of the first component 12 opposite the adhesive composition 30, and a second outer adhesive 60 is added to the first side 29 of the second component 22 opposite the adhesive composition 30. The outer adhesives 50, 60 may be the same or different, and are not particularly limited, so long as the outer adhesives 50, 60 bond to non-conductive objects or elements and function for the intended application. In some embodiments, the outer adhesive is a pressure sensitive adhesive. In some further embodiments, the outer adhesive is an adhesive composition as defined herein. An optional release liner (not shown) may be applied to the first outer adhesive 50, the second outer adhesive 60, or both to protect the outer adhesives during transportation and storage of the article. In some embodiments, a release liner is applied to each of the first and second outer adhesives. In other embodiments, a release liner is applied to one of the outer adhesives for storage and transportation purposes, and the article is rolled on itself, so that the other outer adhesive is in direct contact with the release agent of the release liner. The adhesive composition can then be unrolled when ready for use. The release liner can be made of, for example, kraft paper, polyethylene, polypropylene, polyester, or a composite of any of these materials. These liners are preferably coated with a release agent, such as a fluorochemical or silicone. In some preferred embodiments, the liner is a paper, polyolefin film, or polyester film coated with a silicone release material.Examples of commercially available release liners include POLYSLIK™ silicone release paper available from Loparex (Cary, NC), Silicone 1750 coated film from Infiana (Forchheim, Germany), silicone treated polyethylene terephthalate film available from HP Smith Co. (Stoneham, MA), and 3M Scotchpak™ 9741 release liner from 3M Company (St. Paul, MN).

[0034] In the embodiment shown in FIG. 1C, the first and second components are two-dimensional (e.g., sheets or multi-layer films). However, that is not required, and applications can be envisaged where one or both of the components are three-dimensional (e.g., special mounting features such as molded recesses for seating non-conductive objects). In practice, one of the optional release liners is removed from the first outer adhesive 50, and the first outer adhesive is adhered to a non-conductive object. The second optional release liner is then removed from the second outer adhesive 60, and the second outer adhesive 60 is adhered to a different non-conductive object to adhesively bond the non-conductive objects. The non-conductive objects can be separated on demand by applying an electric potential across the adhesive composition, as illustrated in FIGS. 1A-B. In this case, separation results in one non-conductive object to which the first component is adhesively bonded, and another non-conductive object to which the second component is adhesively bonded.

[0035] FIG. 2 shows another embodiment of an article 110 of the present application in which the adhesive composition is a double-sided tape that bonds first and second components together.

[0036] 2A, the article 110 includes a first component 112 having a first conductive surface 114 and a second component 122 having a second conductive surface 124. The first and second components can be made from conductive material(s) as illustrated in FIG. 2A, or one or both of the first and second components can be made from non-conductive material(s) and at least partially coated with conductive material(s), as described above with respect to FIG. 1. An adhesive composition 130 is disposed between the first conductive surface 114 and the second conductive surface 124 to bond the first component 112 to the second component 122.

[0037] The adhesive composition 130 is a double-sided adhesive further comprising a carrier 170 having a first major surface 172 and a second major surface 174 opposite the first major surface. A first adhesive composition 132 comprising a cured first polymerizable ionic liquid is on the first major surface 172 of the carrier 170. Similarly, a second adhesive composition 134 comprising a cured second polymerizable ionic liquid is on the second major surface 174 of the carrier 170. In some embodiments, the composition of the first polymerizable ionic liquid is the same as the composition of the second polymerizable liquid. In other embodiments, the composition of the first polymerizable liquid is different from the composition of the second polymerizable liquid. A surface 136 of the first adhesive composition 132 opposite the carrier 170 is in contact with the first conductive surface 114 of the first component 112. A surface 138 of the second adhesive composition 134 opposite the carrier 170 is in contact with the second conductive surface 124 of the second component 122 .

[0038] In some embodiments, the carrier is a porous material that allows physical contact between the first adhesive composition and the second adhesive composition. Exemplary carriers include paper, woven or nonwoven fabrics, porous films, metal meshes, metal grids, or combinations thereof. In some embodiments, the carrier is conductive. Such conductive carriers may be porous or non-porous and may include metal meshes, metal grids, metal foils, metal plates, conductive polymers, conductive foams, conductive tissues, or combinations thereof.

[0039] In the embodiment shown in FIG. 2A, the first conductive surface 114 functions as a positive adhesive interface and the second conductive surface 124 functions as a negative adhesive interface. If the carrier is made of a porous material, application of a DC potential 140 across the adhesive composition 130 results in a weakening of the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 124), as measured, for example, according to the work of adhesion per surface area, thus making it easier to separate the second component 122 from the first component 112. When it is desired to separate the adhesive composition from the first component, the polarity of the DC potential can be reversed, thereby causing the first conductive surface to function as a negative adhesive interface.

[0040] When the carrier of FIG. 2A is a non-porous conductive material, application of a DC potential 140 across the adhesive composition 130 can result in a negative adhesive interface (i.e., the second conductive surface 124) and a weakening of the adhesive bond at the first major surface 172 of the carrier 170.

[0041] In another embodiment, the carrier 170 is a conductive material that functions as either a positive or negative adhesive interface during the peeling process. For example, referring to FIG. 2B, the first conductive surface 114 of the first component 112 is the positive adhesive interface and the first major surface 172 of the carrier 170 is the negative adhesive interface. Applying a DC potential 140 across the first adhesive composition 132 separates the first component 112 and the second component 122 at the first major surface 172 of the carrier 170. Alternatively, the first component 112 can be removed from the first adhesive composition 132 by reversing the polarity of the DC potential.

[0042] In an additional embodiment, the conductive surface 124 of the second component 122 or the second major surface 174 of the carrier 170 can be a negative adhesive interface, and the other of the conductive surface 124 of the second component 122 or the second major surface 174 of the carrier 170 can be a positive adhesive interface.

[0043] With reference to FIG. 2B, it should be understood that when the carrier 170 serves as the negative or positive adhesive interface and the first conductive surface 114 of the first component 112 serves as the other of the negative or positive adhesive interfaces, only the first adhesive composition 132 to which the DC potential is applied needs to contain a cured polymerizable ionic liquid. The second adhesive composition 134 can actually be any type of adhesive. Similarly, when the carrier 170 serves as the negative or positive adhesive interface and the second conductive surface 124 of the second component 122 serves as the other of the negative or positive adhesive interfaces, only the second adhesive composition 134 to which the DC potential is applied needs to contain a cured polymerizable ionic liquid. The first adhesive composition 132 can actually be any type of adhesive. Thus, in such an embodiment, a double-sided tape can be used to create an article that includes a carrier with adhesive on both sides, where only one of the adhesives contains a cured polymerizable ionic liquid. This structure is similar to that illustrated in FIG. 1C, where the second component 22 is a carrier.

[0044] As indicated above, double-sided tapes with conductive carriers allow users to more strategically control the release location within an article, which can be particularly advantageous when the adhesive needs to be removed from a component prior to recycling and / or when the adhesive needs to remain on the component for repositioning or adhesion to the same or a different article.

[0045] Furthermore, by using a double-sided tape with a conductive carrier, at least one of the components does not need to be conductive in order to separate a first component from a second component. The carrier can function as one of the electrodes, thus increasing the types of materials that can be included in an article (i.e., bonding two conductive components together, or bonding a conductive component to a non-conductive component).

[0046] The above embodiments illustrate exemplary configurations of the articles of the present disclosure, and methods of delaminating components within these articles. The adhesive compositions will now be described in further detail.

[0047] Adhesive Composition The adhesive composition of the present disclosure comprises a curable polymerizable ionic liquid. The polymerizable ionic liquid comprises: A polymerizable anion and an imidazole compound of formula I [ka] (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R 1 is H or C 1 ~C 25 is an alkyl group, R 2 is H or -CO-X 1 -R 5 and R 5 is H or C 1 ~C 25 is an alkyl group, and X 1 is -O- or -NR 6 - and R 6 is H or C1 -C 6 is alkyl, R 3 is H or CH 3 is preferably H, R 8 is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R 1 and R 2 is H) and a cation corresponding to the conjugate acid of

[0048] In embodiments of Formula I where Z is an azlactone functional group, Z is of the formula: [ka] (In the formula, Each R 9 are independently H or an alkyl group having 1 to 14 carbon atoms, and n is 0 or 1).

[0049] In other embodiments where Z comprises an ester, amide or ketone functionality, Z has the formula -C(O)-(X 1 ) a -R 10 (wherein R 10 is a (hetero)hydrocarbyl group, which is optionally substituted with one or more hydroxyl groups; X 1 is -O- or -NR 6 - and R 6 is H or C 1 ~C 6 alkyl, and a is 0 or 1. Preferably, R 10 is a hydrocarbyl group, more preferably R 10 R is an alkyl group having 1 to 25 carbon atoms. 10 is optionally substituted with a hydroxyl group.

[0050] In some embodiments, R 1is H and R 2 is H and R 3 is H, w is 0, and Z is an ester. In the same or a different embodiment, Z is -C(O)-OR 10 and R 10 is a hydrocarbyl group, which is optionally substituted with a hydroxyl group.

[0051] As used herein, "Acryloyl" is used in a general sense to refer not only to derivatives of acrylic acid but also to amine and alcohol derivatives, respectively; "(Meth)acryloyl" includes both acryloyl and methacryloyl groups, that is, both esters and amides.

[0052] "Poly(meth)acryloyl" means a compound having two or more (meth)acryloyl groups capable of functioning as a Michael acceptor.

[0053] By "curable" it is meant that the coatable material can be converted into a solid, substantially non-flowable material by cooling (to solidify a hot melt), heating (to dry and solidify the material in a solvent), chemical crosslinking, radiation crosslinking, etc.

[0054] "Alkyl" includes straight-chain, branched, and cyclic alkyl groups, including both unsubstituted and substituted alkyl groups. Unless otherwise specified, alkyl groups typically contain 1 to 20 carbon atoms. Examples of "alkyl" as used herein include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, isobutyl, t-butyl, isopropyl, n-octyl, n-heptyl, ethylhexyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl. Unless otherwise noted, alkyl groups can be monovalent or polyvalent.

[0055] "Heteroalkyl" includes both unsubstituted and substituted alkyl groups, as well as straight-chain, branched, and cyclic alkyl groups having one or more heteroatoms independently selected from S, O, and N. Unless otherwise specified, heteroalkyl groups typically contain 1 to 20 carbon atoms. "Heteroalkyl" is a subset of "hydrocarbyl containing one or more S, N, O, P, or Si atoms" below. Examples of "heteroalkyl" as used herein include, but are not limited to, methoxy, ethoxy, propoxy, 3,6-dioxaheptyl, 3-(trimethylsilyl)-propyl, and 4-dimethylaminobutyl. Unless otherwise noted, heteroalkyl groups can be monovalent or polyvalent.

[0056] "Aryl" is an aromatic group containing 6 to 18 ring atoms and may contain any fused rings, which may be saturated, unsaturated, or aromatic. Examples of aryl groups include phenyl, naphthyl, biphenyl, phenanthryl, and anthracyl. Heteroaryl is an aryl containing 1 to 3 heteroatoms such as nitrogen, oxygen, or sulfur and may contain fused rings. Some examples of heteroaryl groups are pyridyl, furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl, indolyl, benzofuranyl, and benzthiazolyl. Unless otherwise noted, aryl and heteroaryl groups may be monovalent or polyvalent.

[0057] "(Hetero)hydrocarbyl" is inclusive of hydrocarbyl alkyl and aryl groups, and heterohydrocarbyl heteroalkyl and heteroaryl groups, the latter containing one or more catenary oxygen heteroatoms, such as ether or amino groups. Heterohydrocarbyls may optionally contain one or more pendant (in-chain) functional groups, such as ester, amide, urea, urethane, and carbonate functional groups. Unless otherwise indicated, non-polymeric (hetero)hydrocarbyl groups typically contain 1 to 60 carbon atoms. Some examples of heterohydrocarbyl as used herein include, but are not limited to, those described above for "alkyl", "heteroalkyl", "aryl", and "heteroaryl", as well as methoxy, ethoxy, propoxy, 4-diphenylaminobutyl, 2-(2'-phenoxyethoxy)ethyl, 3,6-dioxaheptyl, and 3,6-dioxahexyl-6-phenyl.

[0058] The imidazole compounds of formula I are Michael addition products of imidazole compounds with Michael acceptor compounds, i.e., compounds having an electron-deficient double bond and an electron-withdrawing functional group, such as α,β-unsaturated esters, amides, ketones, nitriles, and azlactones.αβSuch compounds can be prepared as described in Scheme I. [ka] (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R 1 is H or C 1 ~C 25 is an alkyl group, R 2 is H or -CO-X 1 -R 5 and R 5 is H or C 1 ~C 25 is an alkyl group, and X 1 is -O- or -NR 6 - and R6 is H or C 1 -C 6 is alkyl, R 3 is H or CH 3 and R 8 is a (hetero)hydrocarbyl group including alkyl and aryl, preferably an alkyl group; and w is 0, 1, 2 or 3.

[0059] Exemplary Michael acceptor compounds include esters of non-tertiary alcohols such as ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 1-hexanol, 2-hexanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, 2-ethyl-1-butanol; 3,5,5-trimethyl-1-hexanol, 3-heptanol, 1-octanol, 2-octanol, isooctyl alcohol, 2-ethyl-1-hexanol, 1-decanol, 2-propylheptanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, citronellol, and dihydrocitronellol with either acrylic or methacrylic acid. Other exemplary Michael acceptors include t-butyl acrylate, methyl methacrylate, isobutyl methacrylate, s-butyl methacrylate, t-butyl methacrylate, stearyl methacrylate, phenyl methacrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, benzyl methacrylate, 3,3,5-trimethylcyclohexyl acrylate, cyclohexyl acrylate, N-octylacrylamide, and propyl methacrylate. Still other exemplary Michael acceptor compounds include 2-hydroxyethyl (meth)acrylate, acrylamide, mono- or di-N-alkyl substituted acrylamide, t-butylacrylamide, dimethylaminoethyl acrylamide, N-octylacrylamide, and poly(alkoxyalkyl)(meth)acrylates (e.g., 2-(2-ethoxyethoxy)ethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-methoxyethoxyethyl (meth)acrylate, 2-methoxyethyl methacrylate, polyethylene glycol mono(meth)acrylate).

[0060] In some embodiments, the imidazole compound can be prepared by a Michael addition reaction of an imidazole compound to a poly(meth)acryloyl compound, as shown in Scheme II: [ka] (In the formula, R 1 is H or C 1 ~C 25 is an alkyl group, R 2 is H or -CO-X 1 -R 5 and R 5 is H or C 1 ~C 25 is an alkyl group, and X 1 is -O- or -NR 6 - and R 6 is H or C 1 -C 6 is alkyl, R 3 is H or CH 3 and R 4 is a (hetero)hydrocarbyl linking group which may further comprise one or more catenary (in-chain) functional groups including ester, amide, urethane and other functional groups, preferably a hydrocarbyl group comprising alkylene, cycloalkylene, or combinations thereof, optionally substituted with one or more hydroxyl groups; R 8 is a (hetero)hydrocarbyl group and w is 0, 1, 2, or 3; X 1 is -O- or NR 6 - and R 6 But H or C 1 ~C 6 is alkyl, x is 1 to 6, preferably 1 to 4; y is 0 to 2; v is x+y).

[0061] As exemplified (above), compounds of formula II can be prepared by Michael addition of an imidazole compound to a polyacryloyl compound. Useful fluorochemical monofunctional compounds include those of the formula: [ka] Contains (In the formula, each 1 is alkylene, -O-, or -NR 6 - selected from, each R 6 each independently represents H or an alkyl group having 1 to 6 carbon atoms; R 1 , R 2 and R 3 are the same as those listed above for Scheme II; R 4 is a (hetero)hydrocarbyl linking group which may further comprise one or more catenary (in-chain) functional groups including ester, amide, urethane and other functional groups, preferably a hydrocarbyl group comprising alkylene, cycloalkylene, or combinations thereof, optionally substituted with one or more hydroxyl groups; v is greater than 1, preferably greater than 2, and generally from 2 to 6.

[0062] In one embodiment, R 4 may be a polyvalent organic group having a valence of at least two. 4 Examples include butylene, ethylene, propylene, and 4-oxaheptalene, hexylene, and 1,4-bis(methyl)cyclohexylene. All isomers or alkylene groups are contemplated, such as 1,2-, 1,3-, and 1,4-butylene isomers. The alkylene may be further substituted with hydroxyl groups, for example, 2-hydroxy-1,3-propylene.

[0063] Useful polyacrylic compounds include, for example, (a) diacrylic-containing compounds, such as ethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, cyclohexanedimethanol diacrylate, alkoxylated hexanediol diacrylate, neopentyl glycol diacrylate, caprolactone-modified neopentyl glycol hydroxypivalate diacrylate, cyclohexanedimethanol diacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, bisphenol-A diacrylate, ethoxylated bisphenol-A diacrylate, hydroxypivalaldehyde-modified trimethylolpropane diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, tetraethylene glycol diacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane diacrylate, triethyl ... ethylene glycol diacrylate, tripropylene glycol diacrylate; (b) triacryl-containing compounds such as glycerol triacrylate, ethoxylated triacrylates (e.g., ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate, propoxylated triacrylates (e.g., propoxylated glyceryl triacrylate, propoxylated trimethylolpropane triacrylate), tris(2-hydroxyethyl)isocyanurate triacrylate; (c) higher functionality acrylic-containing compounds such as ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol tetraacrylate, pentaerythritol tetraacrylate; (d) oligomeric acrylic compounds such as acrylate monomers selected from the group consisting of urethane acrylates, polyester acrylates, epoxy acrylates; polyacrylamide analogs of the foregoing; and combinations thereof.

[0064] Such compounds are available from suppliers such as Sartomer Company, Exton, Pennsylvania, UCB Chemicals Corporation, Smyrna, Georgia, and Aldrich Chemical Company, Milwaukee, Wisconsin. Additional useful acrylate materials include hydantoin moiety-containing polyacrylates, such as those reported in U.S. Pat. No. 4,262,072 (Wendling et al.).

[0065] Other useful polyacrylic compounds include, for example, free radically polymerizable acrylate oligomers and polymers having pendant (meth)acrylic groups, at least two of which are acrylic groups. There is a different reactivity between acrylic and methacrylic groups with respect to Michael-type addition. Michael-type addition typically occurs easily with acrylic groups, but can only occur with difficulty, if at all, with methacrylic groups. For this reason, polyacrylic components typically have at least two acrylic groups (e.g., as part of acryloxy or acrylamide functional groups), but poly(meth)acrylic compounds may also have additional (meth)acrylic groups (e.g., as part of methacrylate or methacrylamide functional groups). Advantageously, compositions can be prepared in which Michael addition occurs via acrylic groups, leaving methacrylic groups unreacted. Such unreacted methacrylic groups can then be free radically polymerized.

[0066] It will be understood that the corresponding amides or thioesters of the above useful polyacrylic compounds are also useful. The polyfunctional ethylenically unsaturated monomer is preferably an ester of acrylic acid. More preferably, it is selected from the group consisting of difunctional ethylenically unsaturated esters of acrylic, trifunctional ethylenically unsaturated esters of acrylic, tetrafunctional ethylenically unsaturated esters of acrylic, and combinations thereof. Of these, difunctional and trifunctional ethylenically unsaturated esters of acrylic acid are more preferred.

[0067] Other useful acrylate oligomers include acrylated epoxies, such as diacrylated esters of epoxy-functional materials (e.g., diacrylated esters of bisphenol A epoxy-functional materials) and acrylated urethanes. Useful acrylated epoxies include, for example, those available under the trade names "EBECRYL 3500", "EBECRYL 3600", "EBECRYL 3700", and "EBECRYL 3720" from UCB Chemicals Corporation. Useful acrylated urethanes include, for example, those available under the trade names "EBECRYL 270", "EBECRYL 1290", "EBECRYL 8301", and "EBECRYL 8804" from UCB Chemicals Corporation.

[0068] The polyfunctional ethylenically unsaturated monomer is preferably an ester of acrylic acid. More preferably, it is selected from the group consisting of difunctional ethylenically unsaturated esters of acrylic, trifunctional ethylenically unsaturated esters of acrylic, tetrafunctional ethylenically unsaturated esters of acrylic, and combinations thereof. Of these, difunctional and trifunctional ethylenically unsaturated esters of acrylic acid are more preferred.

[0069] Preferred polyfunctional ethylenically unsaturated esters of acrylic acid have the formula: [ka] It can be expressed as R 11 is an alkylene, cycloalkylene, or combination thereof, optionally substituted with a hydroxyl group, and generally R 10 is the residue of a polyol, v is greater than 1, preferably greater than 2, and generally ranges from 2 to 6.

[0070] Examples of suitable polyfunctional ethylenically unsaturated esters of acrylic acid are, for example, diacrylic and dimethylacrylic esters of aliphatic diols, such as ethylene glycol, triethylene glycol, 2,2-dimethyl-1,3-propanediol, 1,3-cyclopentanediol, 1-ethoxy-2,3-propanediol, 2-methyl-2,4-pentanediol, 1,4-cyclohexanediol, 1,6-hexamethylenediol, 1,2-cyclohexanediol, 1,6-cyclohexanedimethanol; triacrylic esters of aliphatic triols, such as glycerin, 1,2,3-propanetrimethanol, 1,2,4-butanetriol, 1,2,5 pentanetriol, 1,3,6-hexanetriol, and 1,5,10-decanetriol; triacrylic esters of tris(hydroxyethyl)isocyanurate; tetraacrylic esters of aliphatic triols. and polyacrylic or polymethacrylic acid esters of polyhydric alcohols, including acid esters such as 1,2,3,4-butanetetrol, 1,1,2,2-tetramethylolethane, 1,1,3,3-tetramethylolpropane, and pentaerythritol tetraacrylate; pentaacrylates and pentamethacrylates of aliphatic pentols, such as adonitol; hexaacrylates of hexanol, such as sorbitol and dipentaerythritol; diacrylates of aromatic diols, such as resorcinol, pyrocatechol, bisphenol A, and bis(2-hydroxyethyl)phthalate; triacrylates of aromatic triols, such as pyrogallol, phloroglucinol, and 2-phenyl-2,2-methylolethanol; and hexaacrylates of dihydroxyethylhydantoin; and mixtures thereof.

[0071] The compound of formula II functions as a reactive monomer and is therefore substantially unpolymerized in the curable composition at the time the curable composition is applied to a substrate, and thus the curable composition hardens upon curing by polymerization of the ethylenically unsaturated groups of the (e.g., multifunctional) polymerizable ionic liquid.

[0072] In some preferred embodiments, the compounds of formulas II and IV have sufficiently low viscosity so that they act as reactive diluents.In such embodiments, the composition may advantageously be substantially free of solvent, particularly organic solvents.This can result in increased efficiency in terms of production time and energy consumption by reducing or eliminating the need to dry the composition before curing.This can also reduce the volatile organic component (VOC) emissions of the composition.

[0073] Compounds of formula I where Z is an azlactone functional group can be prepared by Michael addition of an imidazole compound to an azlactone compound, as shown in Scheme III: [ka] (In the formula, R 1 and R 2 is H, R 3 is H or CH 3 and R 8 is a (hetero)hydrocarbyl group including alkyl and aryl, preferably an alkyl group; w is 0, 1, 2 or 3; Each R 9 are independently H or an alkyl group having 1 to 14 carbon atoms, and n is 0 or 1).

[0074] The anionic monomers of the polymerizable ionic liquids have an ethylenically unsaturated polymerizable group and an acid group. The acid functional group may be the acid itself, such as a carboxylic acid, or may in part be its conjugate base. In the presence of an imidazole compound, these acid functional monomers form a conjugate base.

[0075] Useful acid functional monomers include, but are not limited to, those selected from ethylenically unsaturated carboxylic acids, ethylenically unsaturated sulfonic acids, ethylenically unsaturated phosphonic acids, and mixtures thereof. Examples of such compounds include those selected from acrylic acid, methacrylic acid, itaconic acid, fumaric acid, crotonic acid, citraconic acid, maleic acid, oleic acid, β-carboxyethyl (meth)acrylate, 2-sulfoethyl methacrylate, styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid, vinylphosphonic acid, and mixtures thereof.

[0076] Due to their ready availability, acid functional monomers are generally selected from ethylenically unsaturated carboxylic acids, i.e. (meth)acrylic acid. If even stronger acids are desired, acid monomers include ethylenically unsaturated sulfonic acids and ethylenically unsaturated phosphonic acids. Depending on the desired end use and physical properties of the final composition, acid functional monomers can be used in amounts of 5 molar equivalents or more relative to the molar equivalent of imidazole groups. In some embodiments, the molar ratio of acid groups to imidazole groups is approximately equimolar ±20%.

[0077] Preferred polymerizable ionic liquids exhibit high air-to-nitrogen cure exotherm ratios. The air-to-nitrogen cure ratios are typically at least 0.70. In preferred embodiments, the air-to-nitrogen cure exotherm ratios are typically at least 0.80, preferably at least 0.90. In embodiments where the air-to-nitrogen cure ratio of the polymerizable ionic liquid is sufficiently high, the polymerizable ionic liquid can advantageously be substantially completely cured in air (i.e., in an oxygen-rich environment) rather than requiring curing in the absence of oxygen.

[0078] Polymerizable ionic liquids may also include other conventional (e.g., (meth)acrylate) ethylenically unsaturated monomer(s), oligomer(s), or polymer(s). By "any monomer" is meant an ethylenically unsaturated monomer that is not a polymerizable ionic liquid, and includes polar and non-polar monomers and oligomers, as described more fully herein. While conventional monomers are polymerizable and many are liquids at 25° C., conventional monomers are typically non-ionic and lack a cation and an anion.

[0079] Conventional (meth)acrylate monomers typically have an air to nitrogen cure exotherm ratio of 0.50 or less, 0.40 or less, 0.35 or less, 0.20 or less, or 0.25 or less. For example, triethylene glycol dimethacrylate (TEGMA) has been found to have an air to nitrogen cure exotherm ratio of about 0.36, while hydroxyethyl methacrylate (HEMA) has been found to have an air to nitrogen cure exotherm ratio of less than 0.25. Although the photocuring of conventional (meth)acrylate monomers and especially methacrylate monomers is typically inhibited by the oxygen present in air, the inclusion of a (e.g., multifunctional) polymerizable ionic liquid can sufficiently increase the air to nitrogen cure exotherm of the mixture, so that the mixture can advantageously be substantially completely cured in air. In embodiments where the composition is cured in air and the multifunctional polymerizable ionic liquid is combined with "any" polymerizable (meth)acrylate monomer that exhibits a lower air-to-nitrogen cure exotherm ratio, the air-to-oxygen cure exotherm ratio of the (e.g., multifunctional) polymerizable ionic liquid described herein is at least 0.85, preferably at least 0.90, and more preferably at least 0.95.

[0080] The polymerizable ionic liquid composition may further comprise, as an "optional" monomer, a (meth)acrylate ester monomer. The (meth)acrylate ester monomers useful in preparing the acid functional (meth)acrylate adhesive copolymers are (meth)acrylic ester monomers of non-tertiary alcohols, which alcohols contain from 1 to 14 carbon atoms, preferably an average of 4 to 12 carbon atoms.

[0081] Examples of monomers suitable for use as (meth)acrylate ester monomers include esters of non-tertiary alcohols, such as ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 1-hexanol, 2-hexanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, 2-ethyl-1-butanol, 3,5,5-trimethyl-1-hexanol, 3-heptanol, 1-octanol, 2-octanol, isooctyl alcohol, 2-ethyl-1-hexanol, 1-decanol, 2-propylheptanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, citronellol, dihydrocitronellol, and the like, with either acrylic or methacrylic acid. In some embodiments, a combination of two or more different (meth)acrylate ester monomers is suitable, but the preferred (meth)acrylate ester monomers are esters of (meth)acrylic acid with butyl alcohol or isooctyl alcohol, or a combination thereof. In some embodiments, the preferred (meth)acrylate ester monomers are esters of (meth)acrylic acid with alcohols derived from renewable resources, such as 2-octanol, citronellol, dihydrocitronellol, etc. Other suitable monomers include branched long-chain acrylates, such as those described in U.S. Pat. No. 8,137,807 (Clapper et al.), which is incorporated herein by reference. Additional suitable alkyl monomers include secondary alkyl acrylates, such as those described in U.S. Pat. No. 9,102,774 (Clapper et al.).

[0082] In some embodiments, the (meth)acrylic ester monomer is a high T g monomer and has a T of at least 25° C., preferably at least 50° C. g Suitable high Tg monomers include examples of suitable monomers useful in the present invention, which include, but are not limited to, t-butyl acrylate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, s-butyl methacrylate, t-butyl methacrylate, stearyl methacrylate, phenyl methacrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, benzyl methacrylate, 3,3,5-trimethylcyclohexyl acrylate, cyclohexyl acrylate, N-octylacrylamide, and propyl methacrylate or combinations thereof.

[0083] The (meth)acrylate ester monomer is present in an amount of 60 parts by weight to 99.5 parts by weight based on 100 parts total "any" monomer content used to prepare the polymer. Preferably, the (meth)acrylate ester monomer is present in an amount of 80 parts by weight to 95 parts by weight based on 100 parts total monomer content. When a high Tg monomer is included, the copolymer may contain up to 40 parts by weight, preferably up to 20 parts by weight, of the (meth)acrylate ester monomer component from 60 parts by weight to 99.5 parts by weight.

[0084] The polymerizable ionic liquid may further comprise a polar monomer as an optional "other monomer". Polar monomers useful for preparing copolymers have some degree of both oil-soluble and water-soluble properties, resulting in the polar monomer distributing between the water and oil phases during emulsion polymerization. As used herein, the term "polar monomer" does not include acid-functional monomers.

[0085] Representative examples of suitable polar monomers include, but are not limited to, 2-hydroxyethyl (meth)acrylate; N-vinylpyrrolidone; N-vinylcaprolactam; acrylamide; mono- or di-N-alkyl substituted acrylamide; t-butylacrylamide; dimethylaminoethylacrylamide; N-octylacrylamide; poly(alkoxyalkyl)(meth)acrylates such as 2-(2-ethoxyethoxy)ethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-methoxyethoxyethyl (meth)acrylate, 2-methoxyethyl methacrylate, polyethylene glycol mono(meth)acrylate, and the like; alkyl vinyl ethers such as vinyl methyl ether, and the like; and mixtures thereof. Preferred polar monomers include those selected from the group consisting of 2-hydroxyethyl (meth)acrylate and N-vinylpyrrolidinone. The polar monomer may be present in an amount of 0 to 30 parts by weight, preferably 0.5 to 15 parts by weight, based on 100 parts by weight of the "any" monomer.

[0086] The polymerizable ionic liquid may further comprise any "optional" monomer, including vinyl monomers, including vinyl esters (e.g., vinyl acetate and vinyl propionate), styrene, substituted styrenes (e.g., α-methylstyrene), vinyl halides, and mixtures thereof. As used herein, vinyl monomer excludes acid functional monomers, acrylate ester monomers, and polar monomers. Such vinyl monomers are generally used at 0 to 5 parts by weight, preferably 1 to 5 parts by weight, based on 100 parts by weight of "optional" monomer.

[0087] The polymerizable ionic liquid may further include a multifunctional poly(meth)acryloyl monomer incorporated into the blend of polymerizable monomers as a component of the "optional" monomer. Multifunctional acrylates are particularly useful for emulsion or UV polymerization. Examples of useful multifunctional (meth)acrylates include, but are not limited to, di(meth)acrylates, tri(meth)acrylates, and tetra(meth)acrylates, such as 1,6-hexanediol di(meth)acrylate, poly(ethylene glycol) di(meth)acrylate, polybutadiene di(meth)acrylate, polyurethane di(meth)acrylate, and propoxylated glycerin tri(meth)acrylate, and mixtures thereof. The amount and type of multifunctional (meth)acrylate is adjusted according to the particular application.

[0088] Typically, the multifunctional (meth)acrylate is present in an amount of less than 5 parts by weight based on the total dry weight of the adhesive composition. More specifically, the crosslinker may be present in an amount of 0.05 to 20 parts, preferably 0.05 to 1 part, based on the "any" monomer of 100 parts of the adhesive composition.

[0089] In some embodiments, the “optional” monomer is, based on the total weight of the optional monomer components, i. 60% by weight to 99.5% by weight of a (meth)acrylic acid ester monomer; ii. 0% to 30% by weight of a non-acid functional ethylenically unsaturated polar monomer; iii. 0% to 20% by weight of a multifunctional (meth)acrylate; may include:

[0090] In a further embodiment, the “optional” monomeric component comprises, based on the total weight of the optional monomeric components: i. 60 parts by weight to 99.5 parts by weight of a (meth)acrylic acid ester monomer; ii. 0.5 parts by weight to 15 parts by weight of an acid functional ethylenically unsaturated monomer; iii. 0 parts by weight to 30 parts by weight of a non-acid functional ethylenically unsaturated polar monomer; iv. 0 to 5 parts of a vinyl monomer; v.0 to 20 parts of a multifunctional (meth)acrylate; may include:

[0091] Some portion of the (meth)acrylic acid ester monomer units may be hydrolyzed after the copolymer is prepared.

[0092] Optionally, the composition may contain solvents such as alcohols (e.g., propanol, ethanol), ketones (e.g., acetone, methyl ethyl ketone), esters (e.g., ethyl acetate), other non-aqueous solvents (e.g., dimethylformamide, dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrrolidinone), and water.

[0093] Optionally, the compositions may contain additives such as indicators, dyes, pigments, fillers, inhibitors, accelerators, viscosity modifiers, wetting agents, buffers, radical and cationic stabilizers (e.g., BHT), and other similar components that will be apparent to those skilled in the art.

[0094] Polymerizable ionic liquids containing "any" monomer may be prepared by any conventional free radical polymerization method, including solution, radiation, bulk, dispersion, emulsion, and suspension processes. The resulting (co)polymers may be random or block (co)polymers.

[0095] Initiators useful for preparing the (meth)acrylate adhesive copolymers used in the present invention are those that generate free radicals upon exposure to heat that initiate the (co)polymerization of the monomer mixture. For preparing the (meth)acrylate polymers by emulsion polymerization, water-soluble initiators are preferred. Suitable water-soluble initiators include, but are not limited to, potassium persulfate, ammonium persulfate, sodium persulfate, and mixtures thereof; redox initiators such as reaction products of the aforementioned persulfates, and reducing agents such as those selected from the group consisting of sodium metabisulfite and sodium bisulfite; and those selected from the group consisting of 4,4'-azobis(4-cyanopentanoic acid) and its soluble salts (e.g., sodium salt, potassium salt). A preferred water-soluble initiator is potassium persulfate. Suitable oil-soluble initiators include, but are not limited to, azo compounds such as VAZO™ 64 (2,2'-(azobis(isobutyronitrile)) and VAZO™ 52 (2,2'-azobis(2,4-dimethylpentanenitrile)), both available from EI du Pont de Nemours CO., peroxides such as benzoyl peroxide and lauroyl peroxide, and mixtures thereof. A preferred oil-soluble thermal initiator is (2,2'-azobis(isobutyronitrile)). When used, the initiator may be present at about 0.05 parts by weight to about 1 part by weight, preferably about 0.1 parts by weight to about 0.5 parts by weight, based on 100 parts by weight of the monomer components in the pressure-sensitive adhesive.

[0096] Alternatively, the mixture can be polymerized by techniques including, but not limited to, conventional techniques of solvent polymerization, dispersion polymerization, and solventless bulk polymerization. The monomer mixture can include a type and amount of a polymerization initiator, particularly a thermal or photoinitiator, effective to polymerize the comonomers, as previously described.

[0097] A typical solution polymerization process is carried out by adding the monomers, a suitable solvent, and any chain transfer agent to a reaction vessel, adding a free radical initiator, purging with nitrogen, and maintaining the reaction vessel at an elevated temperature (typically in the range of about 40° C. to 100° C.) until the reaction is complete, typically for about 1 hour to 20 hours, depending on the batch size and temperature. Examples of solvents are methanol, tetrahydrofuran, ethanol, isopropanol, acetone, methyl ethyl ketone, methyl acetate, ethyl acetate, toluene, xylene, and ethylene glycol alkyl ethers. These solvents can be used alone or as mixtures thereof.

[0098] In a typical photopolymerization process, the monomer mixture may be irradiated with ultraviolet (UV) light in the presence of a photoinitiator (i.e., photoinitiator). Preferred photoinitiators are available under the trade names IRGACURE™ and DAROCUR™ from Ciba Specialty Chemical Corp., Tarrytown, NY, including 1-hydroxycyclohexyl phenyl ketone (IRGACURE™ 184), 2,2-dimethoxy-1,2-diphenylethan-1-one (IRGACURE™ 185), 2,2-dimethoxy-1,2-diphenylethan-1-one (IRGACURE™ 186), and 2,2-dimethoxy-1,2-diphenylethan-1-one (IRGACURE™ 187). 651), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (IRGACURE® 819), 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one (IRGACURE® 2959), 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone (IRGACURE® 369), 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (IRGACURE® 907), and 2-hydroxy-2-methyl-1-phenylpropan-1-one (DAROCUR® 1173). Particularly preferred photoinitiators are IRGACURE® 819, 651, 184, and 2959.

[0099] Solvent-free polymerization methods may also be utilized to prepare the polymers, such as the continuous free radical polymerization methods described in U.S. Pat. Nos. 4,619,979 and 4,843,134 (Kotnour et al.); the essentially adiabatic polymerization method using a batch reactor described in U.S. Pat. No. 5,637,646 (Ellis); and the method described for polymerizing packaged pre-adhesive compositions described in U.S. Pat. No. 5,804,610 (Hamer et al.).

[0100] Coating Process The polymerizable ionic liquid can be applied to a surface of a component (e.g., a carrier, a substrate, a surface of an article, etc.) using a variety of conventional coating methods. In some embodiments, the polymerizable ionic liquid with any "any" monomer is a pre-adhesive composition that includes a conjugate acid of an imidazole compound of formula I or II and a polymerizable anionic monomer. Suitable coating methods include, for example, spin coating, knife coating, die coating, wire coating, flood coating, padding, spraying, roll coating, dipping, brushing, foaming, and the like. The coating is optionally dried and at least partially, typically fully, cured using an energy source. In some embodiments, the pre-adhesive mixture includes a photoinitiator, and the mixture is cured or partially cured by UV irradiation to form an adhesive composition.

[0101] In some embodiments, the adhesive composition is substantially free of uncured polymerizable ionic liquid, i.e., <10% extractable. The degree of cure can be determined by various methods known in the art. One common method is to determine the amount of uncured material by solvent extraction. In some embodiments, the amount of uncured extractable polymerizable ionic liquid is less than 10% by weight of the cured composition, more preferably less than 5% by weight, and most preferably less than 1% by weight.

[0102] In some embodiments, the adhesive composition after curing has a thickness of at least 10 μm, at least 100 μm, at least 500 μm, or at least 1000 μm. In some embodiments, the adhesive composition has a thickness of up to 2 mm, up to 1000 μm, up to 500 μm, or up to 100 μm. In some embodiments, the adhesive composition has a thickness in the range of 10 μm to 2 mm.

[0103] In some embodiments, the adhesive composition comprises a cured polymerizable ionic liquid. In other embodiments, the adhesive composition is a single-sided tape comprising a carrier and a cured polymerizable ionic liquid applied to one side of the carrier. In yet other embodiments, the adhesive composition is a double-sided tape comprising a carrier and a cured first polymerizable ionic liquid applied to one side of the carrier and a cured second polymerizable ionic liquid applied to the other side of the carrier. The first and second polymerizable ionic liquids can be the same or different. Suitable carrier materials are described above.

[0104] Purpose The articles of the present disclosure can provide many advantages. Components within an article can be separated (i.e., peeled) on demand. As described above, on-demand peeling within an article occurs by applying a DC potential across the adhesive composition to cause weakening of the adhesive bond at the negative adhesive interface (i.e., the negative electrode), thus reducing the effort required to separate components within the article. The weakening of the adhesive bond increases with increasing DC potential (voltage), increasing the duration of the applied DC potential, or a combination thereof. Thus, users can tailor the conditions for on-demand peeling to their application or needs. For example, users can increase the duration of the applied DC potential if the application requires a lower voltage. In some embodiments, on-demand peeling occurs at applied DC potentials of up to 1600V / mm, up to 800V / mm, up to 250V / mm, or up to 90V / mm. In some embodiments, on-demand peeling occurs within less than 20 seconds, less than 15 seconds, less than 10 seconds, less than 5 seconds, less than 3 seconds, or less than 1.5 seconds after application of the applied DC potential.

[0105] The articles of the present disclosure also benefit from the nature and degree of ionic content in the adhesive composition. For example, polymerized ionic content typically provides better adhesion than compositions containing the same ionic content in unpolymerized (i.e., free) form, thus ensuring that components do not prematurely disengage during use. In some embodiments, the adhesive compositions of the present disclosure exhibit a 180° peel from glass at 12 inches / min (30.48 cm / min) of at least 0.5 N / cm, 1.0 N / cm, 1.5 N / cm, 2.0 N / cm, 2.5 N / cm, 3.0 N / cm, 3.5 N / cm, or 4.0 N / cm, measured according to Test Method 1.

[0106] Furthermore, it is possible to achieve higher levels of ion content in the adhesive composition by polymerization of the ionic liquid. In some embodiments, the adhesive composition comprises a polymerized ion content of at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85% or 90%. It has been found that a higher ion content generally improves adhesive debonding upon application of a DC applied potential. The weakening of the adhesive bond during debonding can be measured, for example, by the % change in the work of adhesion per surface area of ​​two components bonded together with the adhesive composition. In some embodiments, the % change in the work of adhesion per surface area at 0V and -25V for 100 seconds is at least 10%, at least 15%, at least 20%, at least 30%, at least 40%, at least 60%, at least 70%, at least 80%, at least 90%, or at least 95%. In some embodiments, the percent change in adhesion work per surface area of ​​a component adhesively bonded to an article with the adhesive composition ranges from 10% to 100%, 10% to 99%, 40% to 99%, 60% to 99%, 70% to 99%, or 80% to 99% over 100 seconds at 0 V and -25 V. In some embodiments, the DC applied potential is sufficient to completely disengage the component from the article without user intervention.

[0107] Thus, components can be securely adhered to one another using the adhesive composition and conveniently separated upon application of a DC applied potential. In some embodiments, the adhesive composition of the present disclosure exhibits a 180° peel from glass of at least 0.5 N / cm at 12 in / min (30.48 cm / min) and a % change in work of adhesion per surface area of ​​at least 10% in 100 seconds at 0V and -25V.

[0108] Another related advantage of the articles of the present application is the ability to determine the location of peeling by the direction of the potential applied across the adhesive composition. The adhesive composition of the present application typically peels from the negative adhesive interface. Preferably, little or no adhesive residue remains on the negative adhesive interface after separation. In some embodiments, less than 10%, less than 5%, or less than 1% of the adhesive composition (by weight) remains on the negative adhesive interface after peeling. In some preferred embodiments, no adhesive composition remains on the negative adhesive interface after peeling. This allows the user to cleanly separate the components at the interface of their choice. In some constructions, it may be possible to peel the adhesive composition at one interface during the life of the article and at another interface at the end of the article's life, as recycling and environmental regulations may require.

[0109] The articles of the present application can provide a variety of on-demand peeling solutions. In robotics, the articles may include a mechanical arm coated at one end with an adhesive composition for use in gripping an object (e.g., a component) used to perform various tasks. For example, the object may be a screwdriver or a soldering device. Once the task is completed, the object can be separated by applying an electrical potential to the adhesive composition. In some embodiments, the separation can be designed such that the adhesive composition remains on the mechanical arm to grip a new, different object.

[0110] The articles of the present application can be used, for example, in animal tracking collars, where researchers typically must sedate the animal during both application and removal of the collar. The articles of the present application can be used to create collars designed to fall off at the end of their life cycle. For example, the collar can be secured around the animal's neck using an adhesive composition. A small battery used to collect tracking information can also be used near the end of the collection cycle to apply a potential across the adhesive composition, which then detaches the adhesive and allows the collar to fall to the ground. The collar can then be retrieved by the researcher using a tracking device.

[0111] In another application, the article can be used in the packaging and shipping industries. The adhesive composition can be used to bind packages together. Upon arrival at the delivery destination, a shipping company employee can apply an electric current to separate the packages for delivery.

[0112] The article may also be part of a device or consumer product that includes one or more components that require periodic service or replacement. For example, a service panel may be adhesively bonded to a housing by an adhesive composition, and the panel may be removed by applying a DC applied potential to the adhesive composition. The panel may then be replaced after service, and in some embodiments, may be repositioned using the same adhesive composition that was originally applied during manufacture.

[0113] The article may also be a multi-component product that has reached the end of its product life cycle, where at least some, if not all, of the components are recyclable. If the components are joined by an adhesive composition, it is possible to cleanly separate the recyclable components by applying a DC potential across the adhesive composition.

[0114] The above applications are not intended to be limiting: the articles and methods of the present application may find use in any of a variety of applications that would benefit from on-demand adhesive removal. EXAMPLES

[0115] The objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. These examples are merely for illustrative purposes and are not intended to limit the scope of the appended claims.

[0116] Unless otherwise noted, all parts, percentages, ratios, etc. in the examples and elsewhere in the specification are by weight. [Table 1]

[0117] Preparation of prepolymer solutions 275 grams (g) of nHA, 150 g of IBOA, 75 g of HEA, and 0.15 g of D1173 were mixed together in a clear glass jar. The glass jar was then purged with nitrogen for 5 minutes to remove dissolved oxygen, and then purged with 0.3 milliwatts per square centimeter (mW / cm) until a coatable viscosity was achieved. 2 The coating was placed in front of ultraviolet (UV) light having an intensity of 100 Hz and a wavelength of 365 nanometers (nm). A typical target for coatable viscosity for this process is about 3000 centipoise (cP) at room temperature.

[0118] Comparative Examples C1-C6 and Examples E1-E8 Preparation of Pre-Adhesive Formulations Pre-adhesive formulations were prepared by mixing the prepolymer solutions with the ingredients summarized in Table 2. The ingredients were combined in the amounts listed and mixed for 24 hours. Polymerizable ion content was calculated on a weight percent basis by summing all ingredients considered to be both ionic and polymerizable. Total ion content was calculated on a weight percent basis by summing all ingredients considered to be ionic. The results are summarized in Table 2.

[0119] Preparation of single layer transfer adhesive The pre-adhesive formulations of Comparative Examples C1-C6 and Examples E1-E6 were each coated between silicone-treated PET release liners (RF02N / RF32N available from SKC Haas, Seoul, South Korea) at a wet coating weight of 0.15 millimeters (mm). The constructions were then coated with approximately 950 millijoules per square centimeter (mJ / cm). 2 ) and cured using UV radiation at 360 nm wavelength.

[0120] Preparation of double-coated adhesive with carrier layer The preparation of the double coated adhesive on a nylon or tissue carrier layer was carried out in a similar manner to the preparation of the single layer transfer adhesive provided above, with the following exceptions: The pre-adhesive formulation of Example E5 was coated between two siliconized PET liners at a thickness of 0.05 mm and exposed to approximately 950 mJ / cm2 of 360 nm wavelength UV radiation. 2 The adhesive was cured using a 0.05 mm layer of tissue or nylon material. The top liner was removed and a 0.05 mm layer of tissue or nylon material was laminated to the exposed surface of the adhesive. A second layer of the same pre-adhesive formulation was coated to a thickness of 0.05 mm on either the nylon or tissue side of the construction, followed by approximately 950 mJ / cm2 of 360 nm wavelength UV radiation. 2 It was cured using. [Table 2]

[0121] Test method 1 180° peel adhesion Peel adhesion is the force required to remove the coated flexible sheeting from the test panel measured at a specific angle and removal rate. In the examples of the present invention, the force is expressed in ounces per width of the coated sheet (oz. / in) and then converted to Newtons / cm. For each test, a 0.5 inch (1.27 cm) wide strip of adhesive coated sheeting approximately 5 inches (12.7 cm) long was cut and one of the release liners was peeled off the coated adhesive. One side of a standard float glass test panel was cleaned using isopropanol and a lint-free wiper, and then an adhesive strip was applied to the clean side of the glass test panel. A heavy rubber roller was used to apply the strip. The free end of the coated strip was folded back so that the removal angle was 180 degrees. This free end was attached to the horizontal arm of the adhesion tester. The glass plate was then secured to the platform of a mechanized instrument that moved away from the scale at a controlled rate (12 inches / min) (30.48 cm / min). The peel test was started approximately one minute after the adhesive was applied to the substrate. The scale reading in ounces was taken during the test as the average of both the peak and minimum forces during the peel. Three peel tests were performed for each example and averaged to obtain the peel adhesion value. The results are summarized in Table 3.

[0122] The failure mode was also recorded for each example during peel adhesion testing, and the results are further summarized in Table 3, where "ad" indicates adhesive failure from the substrate and "co" indicates cohesive failure of the bonded material.

[0123] Test method 2: Work of adhesion per surface area with and without application of electric potential The work of adhesion per surface area required to separate two parallel bonded test surfaces was measured while separating the surfaces through the thickness of the bonded material at a specified removal rate.

[0124] The work of adhesion per surface area is expressed as Newtons per square centimeter of mating surface multiplied by the distance traveled between the plates in centimeters (N / cm). This is done by integrating the area under the curve of tensile force in Newtons (N) plotted against the change in gap between the mating surfaces in centimeters (cm), and then multiplying that value by the square centimeter (cm) of mating test surface. 2 ) was analyzed by dividing by the initial contact area in units of

[0125] Tests were performed using a strain-controlled rheometer (ARES G2, from TA Instruments, New Castle, Delaware) equipped with an electrorheology attachment. The test fixture was a stainless steel parallel plate with a diameter of 8 mm. For temperature control, the bottom plate was attached to a water-cooled Advanced Peltier System (APS, from TA Instruments, New Castle, Delaware). Temperature was regulated at 25 °C for all adhesion tests. For application of potential, an arbitrary waveform generator (33210A, from Keysight Technologies, Santa Rosa, California) was connected to a high-voltage amplifier (Trek Model 609E-6, from Trek Inc., Lockport, New York), which was connected to the upper geometry on the rheometer. The lower geometry was grounded. This allowed for the application of potentials ranging from 0 to ±4000 volts direct current (VDC) to the specimen between the rheometer plates.

[0126] For each test, an 8 mm diameter parallel plate fixture was attached to the rheometer with zero gap between the plates. 8 mm diameter disks were cut from the single layer transfer adhesives (C1-C6 and E1-E6) or the dual coated adhesives (E7 and E8). One of the release liners was peeled off from the disk and the exposed adhesive was applied to a clean surface in the form of a lower 8 mm diameter stainless steel plate of the rheometer. The second release liner was peeled off from the coated adhesive. The temperature was equilibrated at 25°C for 1 minute. The top plate was then lowered and compressed in contact with the adhesive for 500 seconds with a compressive load of 5 N. During the compression process, a DC potential was applied at a voltage of either 0 V DC (as a control test) or -25 V DC during the final 100 seconds of compression loading. At the end of the compression load, the plates were separated at a rate of 0.001 cm / s and the tensile force required to separate the plates was measured as a function of plate separation distance. Three tests were performed for each condition in each example and averaged to obtain the values ​​of work of adhesion per surface area summarized in Table 3.

[0127] The percent reduction in the work of adhesion per surface area was calculated by subtracting each average value at -25V DC applied potential from the corresponding average value with no voltage applied and then dividing the difference by the value with no voltage applied. A positive percent reduction value indicates a reduction in the work of adhesion per surface area after application of a -25V DC potential. These percent reduction values ​​for each example are also summarized in Table 3.

[0128] In the examples tested, a negative DC potential resulted in preferential detachment from the top plate, while a positive DC potential resulted in preferential detachment from the bottom (ground) plate.

[0129] The tensile adhesion profile for Example E4 is shown in Figure 3. Tests were performed with DC potentials of 0V and -25V applied during the last 100 seconds of the compression step. The tensile force in Newtons is plotted on the y-axis and the distance between 8 mm diameter stainless steel parallel plates separated at a rate of 0.01 mm / sec is plotted on the x-axis. The application of a potential reduces the bond strength of the adhesive as shown by the reduction in the work of adhesion (described by the area under the curve). [Table 3]

[0130] FIG. 4 shows a contour surface plot of the work of adhesion per unit surface area (indicated by the gray scale) from the tensile adhesion tests of Example E2 as a function of the DC voltage applied (y-axis) and the duration that the voltage was applied before the plates were separated (x-axis).

[0131] Thus, the present disclosure provides, among other things, articles containing adhesive compositions that exhibit on-demand peel behavior. Various features and advantages of the present disclosure are set forth in the following claims.

Claims

1. a first component having a first conductive surface; a second component having a second surface; and an adhesive composition disposed between the first conductive surface and the second surface, the adhesive composition comprising a cured polymerizable ionic liquid; the adhesive composition bonds the first component to the second component; the effort required to separate the first component from the second component, as measured by the work of adhesion per surface area, is reduced by applying a DC potential across the adhesive composition; The polymerizable ionic liquid is A polymerizable anion and an imidazole compound of formula I 【Chemistry 1】 (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R １ is H or C １ ~C ２５ is an alkyl group, R ２ is H or -CO-X １ -R ５ and R ５ is H or C １ ~C ２５ is an alkyl group, and X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ is alkyl, R ３ is H or CH ３ is preferably H, R ８ is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R １ and R ２ is H) and a cation corresponding to the conjugate acid of

2. R １ is H, and R ２ is H, and R ３ 2. The article of claim 1, wherein: is H, w is 0, Z is --C(O)--O--R.sup.10, and R.sup.10 is a hydrocarbyl group, said hydrocarbyl optionally substituted with a hydroxyl group.

3. The polymerizable anion is an ethylenically unsaturated polymerizable group, a carboxylic acid group (-COOH), a sulfonic acid group (-SO ３ H), sulfate group (-SO ４ H), phosphonic acid group (-PO ３ H ２ ), phosphate group (-OPO ３ and an acidic group selected from the group consisting of:

4. The polymerizable ionic liquid further comprises an optional monomer component, the optional monomer component comprising, based on the total weight of the optional monomer component: i. 60% to 99.5% by weight of a (meth)acrylic acid ester monomer; ii. 0% to 30% by weight of a non-acid functional ethylenically unsaturated polar monomer; iii. 0% to 20% by weight of a multifunctional (meth)acrylate; 2. The article of claim 1, wherein the polymerizable ionic liquid comprises 2% to 75% by weight of the cation, 1% to 35% by weight of the polymerizable anion, and 5% to 95% by weight of the optional monomer component.

5. The article of claim 1 , wherein the second surface of the second component is a second conductive surface.

6. The adhesive composition comprises: a carrier having a first major surface and a second major surface opposite the first major surface; a first adhesive composition on a first major surface of the carrier, the first adhesive composition comprising a cured first polymerizable ionic liquid; a second adhesive composition on a second major surface of the carrier, the second adhesive composition comprising a cured second polymerizable ionic liquid; A double-sided adhesive comprising: a surface of the first adhesive composition opposite the carrier in contact with a first conductive surface of the first component; a surface of the second adhesive composition opposite the carrier in contact with a second surface of the second component; Each of the first and second polymerizable ionic liquids is A polymerizable anion and an imidazole compound of formula I 【Chemistry 2】 (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R １ is H or C １ ~C ２５ is an alkyl group, R ２ is H or -CO-X １ -R ５ and R ５ is H or C １ ~C ２５ is an alkyl group, and X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ is alkyl, R ３ is H or CH ３ is preferably H, R ８ is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R １ and R ２ is H) and a cation corresponding to the conjugate acid of

7. The article of claim 6 , wherein the carrier is a porous material.

8. The article of claim 6 , wherein the carrier is a conductive material.

9. the second surface of the second component is a non-conductive surface, and the adhesive composition is a carrier having a first major surface and a second major surface opposite the first major surface; a first adhesive composition on a first major surface of the carrier, the first adhesive composition comprising a cured first polymerizable ionic liquid; a second adhesive composition on a second major surface of the carrier, the second adhesive composition comprising a cured second polymerizable ionic liquid; A double-sided adhesive comprising: a surface of the first adhesive composition opposite the carrier in contact with a first conductive surface of the first component; a surface of the second adhesive composition opposite the carrier in contact with a second surface of the second component; The carrier is conductive; Each of the first and second polymerizable ionic liquids is A polymerizable anion and an imidazole compound of formula I 【Chemistry 3】 (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R １ is H or C １ ~C ２５ is an alkyl group, R ２ is H or -CO-X １ -R ５ and R ５ is H or C １ ~C ２５ is an alkyl group, and X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ is alkyl, R ３ is H or CH ３ is preferably H, R ８ is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R １ and R ２ is H) and a cation corresponding to the conjugate acid of

10. The article of claim 9 , wherein the carrier is a porous material.

11. 11. The article of any one of claims 1-10, further comprising a first outer adhesive on the first component opposite the adhesive composition, a second outer adhesive on the second component opposite the adhesive composition, or a combination thereof.

12. 2. The article of claim 1, wherein the effort required to separate the first component from the second component is at least 20% as measured by percent change in work of adhesion per surface area in 100 seconds at 0 V and -25 V.

13. 10. A method for separating components in an article according to claim 1, comprising applying a DC potential across the adhesive composition to cause the first component to separate from the second component.

14. 14. The method of claim 13, wherein the second surface of the second component is a second conductive surface, the first conductive surface or the second conductive surface functions as a negative electrode and the other of the first conductive surface or the second conductive surface functions as a positive electrode, the method further comprising applying a DC potential to peel the adhesive composition from the negative electrode and cause separation of the first component from the second component.

15. The adhesive composition comprises: a carrier having a first major surface and a second major surface opposite the first major surface; a first adhesive composition on a first major surface of the carrier, the first adhesive composition comprising a cured first polymerizable ionic liquid; a second adhesive composition on a second major surface of the carrier, the second adhesive composition comprising a cured second polymerizable ionic liquid; A double-sided adhesive comprising: a surface of the first adhesive composition opposite the carrier in contact with a first conductive surface of the first component; a surface of the second adhesive composition opposite the carrier in contact with a second surface of the second component; The carrier is conductive; The first conductive surface or the carrier functions as a negative electrode, and the other of the first conductive surface or the carrier functions as a positive electrode; Each of the first and second polymerizable ionic liquids is A polymerizable anion and an imidazole compound of formula I 【Chemistry 4】 (In the formula, Z comprises a ketone, ester, amide, nitrile, or azlactone functional group; R １ is H or C １ ~C ２５ is an alkyl group, R ２ is H or -CO-X １ -R ５ and R ５ is H or C １ ~C ２５ is an alkyl group, and X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ is alkyl, R ３ is H or CH ３ is preferably H, R ８ is a (hetero)hydrocarbyl group optionally substituted at the 2-, 4- or 5-position, w is 0, 1, 2 or 3; However, when Z contains a nitrile or azlactone functional group, R １ and R ２ is H) and a cation corresponding to the conjugate acid of 15. The method of claim 14, further comprising applying a DC potential to cause the adhesive composition to peel from the negative electrode and separation of the first component from the second component.

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