Articles containing adhesive compositions that exhibit on-demand peeling 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 more broadly to an article comprising two or more components joined together by an adhesive exhibiting on-demand peeling behavior, and more particularly to an article that can be separated into two or more components by applying an electric potential to the adhesive. [Background technology]

[0002] Pressure-sensitive adhesives (PSAs) are commonly used in a variety of industries, including the electronics, automotive, aerospace, polishing, medical device, and packaging industries, to bond components to assembled articles. The bonding strength of the adhesive between components in an article is crucial to achieving desired performance characteristics for specific applications. In many applications, the adhesive must exhibit high peel strength to prevent separation or delamination of components during use. For example, adhesives may be used in the automotive industry to bond trim to the sides of automobiles or trucks. In other applications, the adhesive must be reworkable or repositionable. Typically, PSAs bond more strongly to one component than to another, thus allowing for the repositioning or replacement of the component to which the adhesive bonds more strongly. For example, PSAs may be used to bond protective covers to electronic devices such as mobile phones, personal computers, or computer tablets. Because the cost of the article is high and the cost of the protective cover is relatively low, it may be desirable to remove (peel off) the cover for repair, modification, repositioning of the backing material on the article, or recycling of the bonded article. [Overview of the Initiative]

[0003] Articles containing adhesive compositions capable of controlling the timing of delamination and influencing the surface from which the adhesive delaminates are needed. This disclosure provides articles comprising two or more components bonded together by an adhesive composition exhibiting on-demand delamination behavior upon application of a direct current (DC) potential, and methods for separating the components. The surface from which the adhesive composition delaminates may be influenced by the direction of the potential across the adhesive composition. Articles and methods described herein can be used, for example, in advanced manufacturing (e.g., to grasp parts, transport parts to another location, and release parts on demand), device maintenance (e.g., to delaminate adhesively fixed access panels), and / or recycling for economic or environmental benefits (e.g., to separate components that require different recycling processes).

[0004] In the first embodiment, this disclosure is, A first component having a first conductive surface, A second component having a second surface, An adhesive composition disposed between a first conductive surface and a second surface, comprising an adhesive composition containing 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 adhesive work per unit surface area, is reduced by applying a DC potential across the adhesive composition. Polymerizable ionic liquids, Polymerizable anions and imidazole compounds of formula I [ka] (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R 1 H or C1~C 25 It is an alkyl group, R 2 is H or -CO-X 1 -R5 , wherein R 5 is H or C1-C 25 alkyl group, X 1 is -O- or -NR 6 -, R 6 is H or C1-C6 alkyl, R 3 is H or CH3, preferably H, R 8 is a (hetero)hydrocarbyl group optionally substituted at the 2-position, 4-position or 5-position, w is 0, 1, 2 or 3, with the proviso that when Z comprises a nitrile or azlactone functional group, R 1 and R 2 are H) and a cation corresponding to the conjugate acid of , there is provided an article.

[0005] In another embodiment, the present disclosure provides a method of separating components within 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" means an adhesive or composite (e.g., single-sided or double-sided tape) comprising a cured polymerizable ionic liquid that exhibits on-demand debonding 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

Chemical Formula

[0008] The polymerizable ionic liquid may optionally contain one or more additional components that are blended with it.

[0009] As used herein, the term “on-demand delamination” means the ability to freely reduce the strength of an adhesive bond for the purpose of facilitating the separation (i.e., delamination) of adhesively bonded components.

[0010] As used herein, the terms “pressure-sensitive adhesive” or “PSA” are defined as having the following properties: (1) aggressive and persistent tackiness, (2) adhesion under pressure less than a finger pressure, (3) sufficient ability to adhere to a substrate, and (4) sufficient cohesive force for clean removal from the substrate. Materials found to function well as PSAs include polymers designed and formulated to exhibit the necessary viscoelastic properties, resulting in a desired balance of tackiness, peel adhesion, and shear retention. PSAs are typically characterized by being tacky at room temperature. A PSA is an adhesive that meets the Dahlquist criterion for tackiness, which is typically a shear storage modulus of 3 × 10 when measured at 25°C and 1 Hz (6.28 radians / sec). 5This means the pressure is below Pa (300 kPa). PSA typically exhibits adhesiveness, cohesiveness, conformability, and elasticity at room temperature.

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

[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” applies to compounds, also called “monomers,” that are polymerizable and / or crosslinkable as a result of initiation by thermal decomposition, redox reactions, or photodecomposition. Such compounds have at least one α,β-unsaturated moiety. In some embodiments, monomers having one or more α,β-unsaturated moieties are referred to as “crosslinkers,” but it will be understood that the term “monomer” includes compounds having one or more such moieties as appropriate in the context.

[0014] As used herein, the terms “substantial” or “substantially” mean relatively small variations or aberrations from the stated properties, values, ranges of values, content, formulas, etc., and do not preclude the presence of additional materials, broader ranges of values, etc., that do not substantially affect the desired properties of a given composition, article, product, or method.

[0015] In this specification, the terms “including” and variations thereof are not limited in meaning when they appear in the specification and claims. Such terms are understood to suggest that they include one or more processes or elements described, but not that any other one or more processes or elements, or any other group of processes or elements, is excluded. “Consisting of” means including and limiting to everything that precedes the phrase “consisting of.” Thus, the phrase “consisting of” indicates that the enumerated elements are necessary or essential, and that other elements cannot be present. “Essentially consisting of” means including all elements enumerated after the phrase, and any other elements that do not interfere with or contribute to the activity or action identified in this disclosure with respect to the enumerated elements. Thus, the phrase “essentially consisting of” indicates that the enumerated elements are necessary or essential, but the other elements are optional and may or may not be present, depending on whether they substantially affect the activity or action of the enumerated elements.

[0016] In this application, terms such as “a,” “an,” and “the” are not intended to refer only to singular entities, but include general classifications, and specific examples of such general classifications may be used for illustrative purposes. 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 an enumeration refer to any one item in the enumeration, and any combination of two or more items in the enumeration.

[0017] As used herein, the term "or" is used in its ordinary sense, generally including "and / or," unless otherwise specified. The term "and / or" means one or all of the enumerated elements, or any combination of two or more of the enumerated elements.

[0018] Furthermore, in this specification, all numbers are considered to be modified by the term “about,” and in certain embodiments, by the term “exactly.” As used herein, in relation to a measured quantity, the term “about” refers to the variation of the measured quantity that can be predicted by a person skilled in the art who performs the measurement and exercises a level of care commensurate with the purpose of the measurement and the precision of the measuring instrument used. In this specification, the “maximum” number (e.g., maximum 50) includes that number (e.g., 50).

[0019] Furthermore, in this specification, the description of a numerical range by endpoints includes all numbers and their endpoints that are included within that range (for example, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, etc.).

[0020] Any reference to “several embodiments” throughout this specification means that any particular feature, configuration, composition, or characteristic described in relation to an embodiment is included in at least one embodiment of this disclosure. Therefore, the appearance of such phrase in various places throughout this specification does not necessarily refer to the same embodiment of this disclosure. Furthermore, any particular feature, configuration, composition, or characteristic may be combined in any preferred manner in one or more embodiments.

[0021] The terms “preferred” and “preferred” refer to embodiments of the disclosure that may provide a particular benefit under certain circumstances, but other embodiments may be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unhelpful, nor is it intended to exclude other embodiments from the scope of the disclosure.

[0022] The above summary of this disclosure is not intended to describe each of the disclosed embodiments or all implementations of this disclosure. The following description provides more specific examples of exemplary embodiments. [Brief explanation of the drawing]

[0023] [Figure 1A]This is a schematic side view of one exemplary article of the present application. [Figure 1B] This is a schematic side view of a modified example of the article in Figure 1A. [Figure 1C] This is a schematic side view of another modified example of the article in Figure 1A. [Figure 2A] This is a schematic side view of another exemplary article of this application. [Figure 2B] This is a schematic side view of a modified example of the article in Figure 2A. [Figure 3] This is a plot of the tensile force (Newtons) (y-axis) versus the distance (millimeters) (x-axis) between two 8mm stainless steel plates separated at a speed of 0.01 mm / s in Example E4. [Figure 4] This is a contour surface plot of the bonding work per unit surface area (indicated by shading on the scale) from the tensile bonding test of Example E2, as a function of the applied DC voltage (y-axis) and the duration of voltage application before separating the plates (x-axis).

[0024] When referring to the figures, similar reference numbers (e.g., 12 and 112 or 30 and 130) when excluding multiples of 100 indicate similar elements. Unless otherwise specified, all figures and drawings in this document are not to scale and are selected for the purpose of illustrating different embodiments of the invention. In particular, the dimensions of various components are described only in exemplary terms, and the relationships between the dimensions of various components should not be inferred from the drawings unless otherwise specified. [Modes for carrying out the invention]

[0025] The following description of exemplary embodiments refers to the appended drawings, which form part of this specification and illustrate specific embodiments. It should be understood that other embodiments may be utilized and structural modifications made without departing from the scope of the invention.

[0026] Articles of this 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) comprises an adhesive containing a cured polymerizable ionic liquid and exhibits on-demand peeling behavior when exposed to a DC potential. For example, the effort required to separate the first component from the second component, as measured by the adhesive work per unit 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 articles in this disclosure are not particularly limited. An article may be a finished product or a component incorporated into or attached to another object. Typically, an article consists of at least two components that can be bonded together, and the article may have the shape of a two-dimensional or three-dimensional body. Similarly, the shape and form of the components constituting the article are not particularly limited. A component may be a single element or a combination of elements, and a component may have the shape 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 (for example, one end of a composite strip of material may be folded over and bonded 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 before the components are separated. For example, the potential may be applied across two conductive components on either side of the adhesive composition such that the surface of one component acts as the negative electrode (or negative adhesive interface) and the surface of the other component acts as the positive electrode (or positive adhesive interface). Alternatively, the potential may be applied across one conductive component and a conductive adhesive carrier of the double-sided tape such that the surface of the conductive component or conductive adhesive carrier acts as the negative adhesive interface and the other surface of the conductive component or conductive adhesive carrier acts as the 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 within the article. The location of separation can be reversed simply by changing the polarity of the potential.

[0029] Figure 1 shows one embodiment of an article of the present disclosure comprising two conductive components joined together by an adhesive composition. Referring to Figure 1A, article 10 includes 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 and 22 are each made from a conductive material. The properties of the conductive material are 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 compositions of the first and second conductive surfaces 14 and 24 are the same.

[0030] The adhesive composition 30 bonds the first and second components 12 and 22 to each other on the first conductive surface 14 and the second conductive surface 24. The adhesive composition exhibits on-demand peel behavior by applying a DC potential to the entire adhesive composition 30. In this particular embodiment, the first conductive surface 14 acts as the positive adhesive interface, and the second conductive surface 24 acts as the negative adhesive interface. Applying a DC potential 40 across the adhesive composition 30 results in weakening of the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 24), as measured, for example, according to the adhesive work per unit surface area, and thus makes 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 can be reused, allowing the first component 12 to be rejoined to the second component 22, or to be bonded to a completely different component or article. If it is desirable for the adhesive to remain on the second component 22 after separation, the polarity of the DC potential can be reversed, thereby allowing the first conductive surface 14 to function as a negative adhesive interface.

[0031] The conductive components include components made entirely from a conductive material, as shown in Figure 1A, and components made from a non-conductive material coated with a conductive material, as shown in Figure 1B. Referring to Figure 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 may be made entirely from a conductive material, and the other components may be made from a non-conductive material coated with a conductive material. The conductive coating may only partially coat the component, as shown in Figure 1B, or it 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 when a DC potential is applied across the adhesive composition is sufficiently coated to weaken the adhesive bond at the negative adhesive interface. In some embodiments, the coating is a solid layer. In other embodiments, the coating is pattern-coated on the surface of the component. As described above, the conductive material is not particularly limited and may 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 in Figure 1B bonds the first and second components 12 and 22 to each other. The first conductive surface 14 acts as a positive adhesive interface, and the second conductive surface 24 acts as a negative adhesive interface. Applying a DC potential 40 across the adhesive composition 30 weakens the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 24), as measured, for example, according to the adhesive work per unit surface area, thus making it easier to separate the second component 22 from the first component 12. If it is desirable that the adhesive composition remain mainly on the second component, the polarity of the DC potential can be reversed, thereby allowing the first conductive surface to function as a negative adhesive interface.

[0033] The articles in Figures 1A-B can be further adapted to bond non-conductive objects or elements using an adhesive composition, and then peel them off, as shown in Figure 1C. The article in 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 to each other by an adhesive composition 30. The first and second components may be made from conductive materials, but it should also be understood that the first and / or second components may be made from non-conductive materials and coated with conductive materials, as shown 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 to the adhesive composition 30, and a second outer adhesive 60 is added to the first side 29 of the second component 22 opposite to the adhesive composition 30. The outer adhesives 50, 60 may be the same or different, and are not particularly limited insofar as they bond to a non-conductive object or element and function for their intended use. 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. To protect the outer adhesive during transport and storage of the article, an optional release liner (not shown) may be applied to the first outer adhesive 50, the second outer adhesive 60, or both. In some embodiments, the 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 transport purposes, and the other outer adhesive is in direct contact with the release agent of the release liner by the article being rolled up on itself. The adhesive composition can then be unrolled when ready for use. The release liner may 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 paper, polyolefin film, or polyester film coated with a silicone release agent.Examples of commercially available release liners include POLYSLIK® silicone release paper from Loparex (Cary, NC), Silicone 1750 coated film from Infiana (Forchheim, Germany), silicone-treated polyethylene terephthalate film from HPSmith Co. (Stoneham, MA), and 3M Scotchpak® 9741 release liner from 3M Company (St. Paul, MN).

[0034] In the embodiment shown in Figure 1C, the first and second components are two-dimensional (e.g., sheets or multilayer films). However, this is not essential, and applications where one or both components are three-dimensional can be considered (e.g., special mounting features such as molded recesses for seating nonconductive objects). In practice, one of the optional release liners is removed from the first outer adhesive 50, and the first outer adhesive is bonded to the nonconductive object. Then, one of the second optional release liners is removed from the second outer adhesive 60, and the second outer adhesive 60 is bonded to a different nonconductive object, thereby bonding the nonconductive objects. The nonconductive objects can be separated on demand by applying a potential to the entire adhesive composition, as shown in Figures 1A-B. In this case, the separation yields one nonconductive object to which the first component is bonded, and the other nonconductive object to which the second component is bonded.

[0035] Figure 2 shows another embodiment of Article 110 of the present application, in which the adhesive composition is a double-sided tape that joins the first and second components together.

[0036] Referring to Figure 2A, 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 may be made from a conductive material, as shown in Figure 2A, or one or both of the first and second components may be made from a non-conductive material, as described above with respect to Figure 1, and at least partially coated with a conductive material. The 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 main surface 172 and a second main surface 174 opposite to the first main surface. The first adhesive composition 132, containing a cured first polymerizable ionic liquid, is located on the first main surface 172 of the carrier 170. Similarly, the second adhesive composition 134, containing a cured second polymerizable ionic liquid, is located on the second main 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. The surface 136 of the first adhesive composition 132, opposite to the carrier 170, is in contact with the first conductive surface 114 of the first component 112. The surface 138 of the second adhesive composition 134 opposite to 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. Examples of 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 nonporous 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 Figure 2A, the first conductive surface 114 functions as a positive adhesive interface, and the second conductive surface 124 functions as a negative adhesive interface. When the carrier is made from a porous material, the 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 adhesive work per unit surface area, thus making it easier to separate the second component 122 from the first component 112. If it is desirable to separate the adhesive composition from the first component, the polarity of the DC potential can be reversed, thereby allowing the first conductive surface to function as a negative adhesive interface.

[0040] When the carrier in Figure 2A is a non-porous conductive material, applying a DC potential 140 across the adhesive composition 130 can result in a weakening of the adhesive bond at the negative adhesive interface (i.e., the second conductive surface 124) and the first main 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 Figure 2B, the first conductive surface 114 of the first component 112 is a positive adhesive interface, and the first principal surface 172 of the carrier 170 is a negative adhesive interface. When a DC potential 140 is applied across the first adhesive composition 132, the first component 112 and the second component 122 separate at the first principal 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 additional embodiments, the conductive surface 124 of the second component 122 or the second main 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 main surface 174 of the carrier 170 can be a positive adhesive interface.

[0043] Referring to Figure 2B, it should be understood that if carrier 170 functions as a negative or positive adhesive interface and the first conductive surface 114 of the first component 112 functions as the other negative or positive adhesive interface, then only the first adhesive composition 132 to which the DC potential is applied needs to contain a curable polymerizable ionic liquid. The second adhesive composition 134 can actually be any type of adhesive. Similarly, if carrier 170 functions as a negative or positive adhesive interface and the second conductive surface 124 of the second component 122 functions as the other negative or positive adhesive interface, then only the second adhesive composition 134 to which the DC potential is applied needs to contain a curable polymerizable ionic liquid. The first adhesive composition 132 can actually be any type of adhesive. Thus, in such embodiments, double-sided tape can be used to produce an article containing a carrier with adhesive on both sides, where only one side of the adhesive contains a curable polymerizable ionic liquid. This structure is similar to that illustrated in Figure 1C, where the second component 22 is the carrier.

[0044] As shown above, double-sided tapes with conductive carriers allow users to more strategically adjust the peel position within an article. This can be particularly advantageous when adhesive needs to be removed from a component before recycling, and / or when adhesive needs to be left on a component for repositioning or bonding to the same or a different article.

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

[0046] The embodiments described above illustrate exemplary configurations of the articles of this disclosure and methods for removing components within these articles. The adhesive compositions are described in further detail here.

[0047] Adhesive composition The adhesive composition of this disclosure comprises a curable polymerizable ionic liquid. The polymerizable ionic liquid is Polymerizable anions and imidazole compounds of formula I [ka] (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R 1 H or C1~C 25 It is an alkyl group, R 2 is H or -CO-X 1 -R 5 And R 5 H or C1~C 25 It is an alkyl group, X 1 -O- or -NR 6 - and R 6 is H or C1-C6 alkyl, R3 is H or CH3, preferably H. R 8 is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R 1 and R 2 (is H) It contains a cation corresponding to the conjugate acid of the cation.

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

[0049] In other embodiments, where Z is an ester, amide, or ketone functional group, Z is the formula -C(O)-(X 1 ) a -R 10 It is (in the formula, R 10 is a (hetero)hydrocarbyl group, and this (hetero)hydrocarbyl is optionally substituted with one or more hydroxyl groups, X 1 -O- or -NR 6 - and R 6 (where is H or C1-C6 alkyl, and a is 0 or 1). Preferably, R 10 is a hydrocarbyl group, more preferably R 10 R is an alkyl group consisting of 1 to 25 carbon atoms. 10 It is optionally substituted with a hydroxyl group.

[0050] In some embodiments, R 1 H is R 2 H is R 3 is H, w is 0, and Z is an ester. In the same or different embodiments, Z is -C(O)-OR10 And R 10 This is a hydrocarbyl group, and this hydrocarbyl is optionally substituted with a hydroxyl group.

[0051] When used in this specification, The term "acryloyl" is used in a general sense and refers not only to derivatives of acrylic acid but also to amine derivatives and alcohol derivatives, respectively. "(meth)acryloyl" contains both acryloyl and methacryloyl groups, that is, it contains both esters and amides.

[0052] "Poly(meth)acryloyl" refers to a compound having two or more (meth)acryloyl groups that can function as a Michael acceptor.

[0053] "Curable" means that a coatable material can be converted into a solid, substantially non-flowing material by means of cooling (to solidify the hot melt), heating (to dry and solidify the material in a solvent), chemical crosslinking, radiation crosslinking, etc.

[0054] "Alkyl" includes linear, branched, and cyclic alkyl groups, and includes both unsubstituted and substituted alkyl groups. Unless otherwise indicated, 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 may be monovalent or polyvalent.

[0055] "Heteroalkyl" encompasses both unsubstituted and substituted alkyl groups, as well as linear, branched, and cyclic alkyl groups having one or more heteroatoms independently selected from S, O, and N. Unless otherwise indicated, heteroalkyl groups typically contain 1 to 20 carbon atoms. "Heteroalkyl" is a subset of the "hydrocarbyls containing one or more S, N, O, P, or Si atoms" described 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 may be monovalent or polyvalent.

[0056] An "aryl" is an aromatic group containing 6 to 18 ring atoms, which may contain any fused ring, which may be saturated, unsaturated, or aromatic. Examples of aryl groups include phenyl, naphthyl, biphenyl, phenanthryl, and anthracyl. A heteroaryl is an aryl group containing 1 to 3 heteroatoms, such as nitrogen, oxygen, or sulfur, which may contain a fused ring. 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" encompasses hydrocarbyl alkyl and aryl groups, as well as heterohydrocarbyl heteroalkyl and heteroaryl groups, the latter of which contain one or more catenary oxygen heteroatoms, such as ether or amino groups. Heterohydrocarbyl may optionally contain one or more suspended (in-chain) functional groups, such as ester functional groups, amide functional groups, urea functional groups, urethane functional groups, and carbonate functional groups. Unless otherwise specified, nonpolymeric (hetero)hydrocarbyl groups typically contain 1 to 60 carbon atoms. Some examples of heterohydrocarbyl as used herein, but not limited to these, include methoxy, ethoxy, propoxy, 4-diphenylaminobutyl, 2-(2'-phenoxyethoxy)ethyl, 3,6-dioxaheptyl, and 3,6-dioxahexyl-6-phenyl, in addition to those described above for "alkyl," "heteroalkyl," "aryl," and "heteroaryl."

[0058] The imidazole compounds of formula I are Michael addition products of an imidazole compound and a Michael acceptor compound, 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 azulactones. Such compounds can be prepared as described in scheme I. [ka] (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R 1 H or C1~C 25 It is an alkyl group, R 2 is H or -CO-X 1 -R 5 And R 5 H or C1~C 25 It is an alkyl group, X 1 -O- or -NR 6 - and R 6 is H or C1-C6 alkyl, R 3 is H or CH3, R 8 w is a (hetero)hydrocarbyl group containing alkyl and aryl groups, preferably alkyl groups, where w is 0, 1, 2, or 3.

[0059] Examples of 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 acid 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. Further exemplary Michael acceptor compounds include 2-hydroxyethyl (meth)acrylate, acrylamide, mono- or di-N-alkyl-substituted acrylamide, t-butylacrylamide, dimethylaminoethylacrylamide, N-octylacrylamide, and poly(alkoxyalkyl)(meth)acrylate (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 the imidazole compound to a poly(meth)acryloyl compound, as shown in Scheme II: [ka] (In the formula, R 1 H or C1~C 25 It is an alkyl group, R 2 is H or -CO-X 1 -R 5 And R 5 H or C1~C 25 It is an alkyl group, X 1 -O- or -NR 6 - and R 6 is H or C1-C6 alkyl, R 3 is H or CH3, R 4 This is a (hetero)hydrocarbyl linking group which may further contain one or more catenary (intrachain) functional groups including esters, amides, urethanes, and other functional groups, and is preferably a hydrocarbyl group which is optionally substituted with one or more hydroxyl groups and is an alkylene, cycloalkylene, or a combination thereof. R 8 w is a (hetero)hydrocarbyl group, and w is 0, 1, 2, or 3. X 1 is -O- or NR 6 - and R 6 However, it is H or C1-C6 alkyl, x is between 1 and 6, preferably between 1 and 4. y is between 0 and 2. v is x + y).

[0061] As illustrated above, the compounds of formula II can be prepared by Michael addition of an imidazole compound to a polyacryloyl compound. Useful fluorochemical monofunctional compounds include the following: [ka] includes those meeting this definition (wherein each X 1 is selected from alkylene, -O-, or -NR 6 -, and each R 6 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 enumerated above for Scheme II, R 4 is a (hetero)hydrocarbyl linking group that may further comprise one or more catenary (in-chain) functional groups including ester, amide, urethane and other functional groups, and is preferably a hydrocarbyl group comprising alkylene, cycloalkylene, or a combination thereof, optionally substituted with one or more hydroxyl groups, v is greater than 1, preferably 2 or greater, and generally from 2 to 6).

[0062] In one embodiment, R 4 may be a polyvalent organic group having a valence of at least 2. Examples of the polyvalent group R 4 include butylene, ethylene, propylene, 4-oxaheptalene, hexylene, and 1,4-bis(methyl)cyclohexylene. All isomers or alkylene groups such as 1,2-, 1,3- and 1,4-butylene isomers are contemplated. The alkylene may be further substituted with a hydroxyl group, 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, tricyclodecanedimethanol diacrylate, and (b) Ethylene glycol diacrylate, tripropylene glycol diacrylate; (c) Triacrylic-containing compounds, e.g., glycerol triacrylate, ethoxylated triacrylate (e.g., ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate, propoxylated triacrylate (e.g., propoxylated glyceryl triacrylate, propoxylated trimethylolpropane triacrylate), tris(2-hydroxyethyl) isocyanurate triacrylate); (d) Highly functional acrylic-containing compounds, e.g., ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol tetraacrylate, pentaerythritol tetraacrylate; (e.g., oligomeric acrylic compounds, e.g., urethane acrylate, polyester acrylate, epoxy acrylate; the aforementioned polyacrylamide analogs; and acrylate monomers selected from the group consisting of 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-containing polyacrylates, such as those reported in U.S. Patent No. 4,262,072 (Wendling et al.).

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

[0066] With respect to the above-mentioned useful polyacrylic compounds, it will be understood that corresponding amides or thioesters are also useful. The polyfunctional ethylenically unsaturated monomer is preferably an ester of acrylic acid. More preferably, this 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, for example, diacrylated esters of epoxy-functional materials (for example, diacrylated esters of bisphenol A epoxy-functional materials), and acrylated urethanes. Examples of useful acrylated epoxies include acrylated epoxies available under the trade designations "EBECRYL 3500", "EBECRYL 3600", "EBECRYL 3700", and "EBECRYL 3720" from UCB Chemicals Corporation. Examples of useful acrylated urethanes include acrylated urethanes available under the trade designations "EBECRYL 270", "EBECRYL 1290", "EBECRYL 8301", and "EBECRYL 8804" from UCB Chemicals Corporation.

[0068] The multifunctional 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 acid, trifunctional ethylenically unsaturated esters of acrylic acid, tetrafunctional ethylenically unsaturated esters of acrylic acid, and combinations thereof. Of these, difunctional and trifunctional ethylenically unsaturated esters of acrylic acid are more preferred.

[0069] Preferred multifunctional ethylenically unsaturated esters of acrylic acid are represented by the following formula:

Chemical Formula

[0070] Examples of suitable polyfunctional ethylenically unsaturated acrylic acid esters include, for example, diacrylic and dimethylacrylic acid 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, and 1,6-cyclohexanedimethanol; triacrylic acid 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 acid esters of tris(hydroxyethyl)isocyanurate; and tetraacrylic acid esters of aliphatic triols. Polyacrylic or polymethacrylic 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; pentaacrylic and pentamethacrylic esters of aliphatic pentols, such as adonitol; hexaacrylic esters of hexanols, such as sorbitol and dipentaerythritol; diacrylic esters of aromatic diols, such as resorcinol, pyrocatechol, bisphenol A, and bis(2-hydroxyethyl)phthalate; triacrylic esters of aromatic triols, such as pyrogallol, phloroglucinol, and 2-phenyl-2,2-methylolethanol; and hexaacrylic esters of dihydroxyethyl hydantoin; 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 the substrate. Thus, the curable composition cures upon curing by polymerization of ethylenically unsaturated groups in a polymerizable ionic liquid (e.g., polyfunctional).

[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 solvents, particularly organic solvents. This can result in increased efficiency in terms of manufacturing time and energy consumption by reducing or eliminating the need to dry the composition before curing. This can also reduce the release of volatile organic compounds (VOCs) from the composition.

[0073] Compounds of formula I, where Z is an azulactone functional group, can be prepared by Michael addition of an imidazole compound to an azulactone compound, as shown in scheme III: [ka] (In the formula, R 1 and R 2 H is, R 3 is H or CH3, R 8 w is a (hetero)hydrocarbyl group containing alkyl and aryl groups, preferably alkyl groups, where w is 0, 1, 2, or 3. Each R 9 (where n is independently H, or an alkyl group having 1 to 14 carbon atoms, and n is 0 or 1).

[0074] The anionic monomers of polymerizable ionic liquids have an ethylenically unsaturated polymerizable group and an acidic group. The acidic functional group may be an acid itself, such as a carboxylic acid, or partly its conjugate base. In the presence of an imidazole compound, these acidic 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 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-methylpropanesulfonic acid, vinylphosphonic acid, and mixtures thereof.

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

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

[0078] The polymerizable ionic liquid may also contain other conventional (e.g., (meth)acrylate) ethylenically unsaturated monomers, oligomers, or polymers. “Any monomer” means an ethylenically unsaturated monomer that is not a polymerizable ionic liquid, and includes polar and nonpolar monomers and oligomers, as more fully described herein. Conventional monomers are polymerizable and many are liquid at 25°C, but conventional monomers are typically nonionic and lack cations and anions.

[0079] Conventional (meth)acrylate monomers typically have an air-to-nitrogen curing exothermic 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 curing exothermic ratio of about 0.36, while hydroxyethyl methacrylate (HEMA) has been found to have an air-to-nitrogen curing exothermic ratio of less than 0.25. The photocuring of conventional (meth)acrylate monomers, and especially methacrylate monomers, is typically inhibited by oxygen present in the air, but by including (e.g., polyfunctional) polymerizable ionic liquids, the heat of curing of the mixture from air to nitrogen can be sufficiently increased, resulting in the mixture being advantageously cured substantially completely in air. In embodiments in which the composition is cured in air and the polyfunctional polymerizable ionic liquid is combined with any polymerizable (meth)acrylate monomer exhibiting a lower air-to-nitrogen curing exothermic ratio, the air-to-oxygen curing exothermic ratio of the (e.g., polyfunctional) 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 contain (meth)acrylate ester monomers as "optional" monomers. (Meth)acrylate ester monomers useful for the preparation of acid-functionalized (meth)acrylate adhesive copolymers are (meth)acrylic ester monomers of non-tertiary alcohols, which contain 1 to 14 carbon atoms, preferably on average 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, etc., with either acrylic acid or methacrylic acid. In some embodiments, combinations of two or more different (meth)acrylate ester monomers are preferred, but preferred (meth)acrylate ester monomers are esters of butyl alcohol or isooctyl alcohol, or a combination thereof, with (meth)acrylic acid. In some embodiments, preferred (meth)acrylate ester monomers are esters of (meth)acrylic acid with alcohols derived from renewable resources such as 2-octanol, citronellol, and dihydrocitronellol. Other suitable monomers include branched long-chain acrylates, such as those described in U.S. Patent No. 8,137,807 (Clapper et al.), which is incorporated herein by reference. Additional preferred alkyl monomers include secondary alkyl acrylates, such as those described in U.S. Patent No. 9,102,774 (Clapper et al.).

[0082] In some embodiments, the (meth)acrylic acid ester monomer is high T g A monomer is contained in a T at least 25°C, preferably at least 50°C. g It is desirable to have the following characteristics. Suitable high-Tg monomers include, but are not limited to, examples of suitable monomers useful in the present invention, such as 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 monomer is present in an amount of 60 to 99.5 parts by weight, based on the total "any" monomer content of 100 parts by weight used to prepare the polymer. Preferably, the (meth)acrylate monomer is present in an amount of 80 to 95 parts by weight, based on the total monomer content of 100 parts by weight. When high Tg monomers are present, the copolymer may contain 60 to 99.5 parts by weight of the (meth)acrylate monomer component, up to 40 parts by weight, preferably up to 20 parts by weight.

[0084] The polymerizable ionic liquid may further contain polar monomers as optional “other monomers.” Polar monomers useful for copolymer preparation possess some degree of both oil-soluble and water-soluble properties, resulting in their distribution between the aqueous and oil phases during emulsion polymerization. As used herein, the term “polar monomer” does not include acid-functional monomers.

[0085] Typical 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, etc.; alkyl vinyl ethers, such as vinyl methyl ether, etc.; 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 any monomer.

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

[0087] The polymerizable ionic liquid may further contain polyfunctional poly(meth)acryloyl monomers incorporated into the blend of polymerizable monomers as components of "any" monomers. Polyfunctional acrylates are particularly useful for emulsion polymerization or UV polymerization. Examples of useful polyfunctional (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, as well as mixtures thereof. The amount and type of polyfunctional (meth)acrylate are adjusted according to the specific application.

[0088] Typically, the polyfunctional (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 crosslinking agent may be present in an amount of 0.05 to 20 parts, preferably 0.05 to 1 part, based on any monomer of 100 parts of the adhesive composition.

[0089] In some embodiments, the "any" monomer is determined based on the total weight of any monomer component. i. 60% to 99.5% by weight of (meth)acrylic acid ester monomer, ii. 0% to 30% by weight of non-acid-functionalized ethylenically unsaturated polar monomers, iii.0% to 20% by weight of polyfunctional (meth)acrylates, It may include.

[0090] In further embodiments, the "any" monomer component is determined based on the total weight of the any monomer component. i. 60 to 99.5 parts by weight of (meth)acrylic acid ester monomer, ii. 0.5 to 15 parts by weight of an acid-functionalized ethylenically unsaturated monomer, iii.0 to 30 parts by weight of a non-acid-functionalized ethylenically unsaturated polar monomer, iv.0 to 5 parts vinyl monomer, Parts 0 to 20 of polyfunctional (meth)acrylates, It may include.

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

[0092] Optionally, the composition may contain a solvent (e.g., alcohol (e.g., propanol, ethanol), ketone (e.g., acetone, methyl ethyl ketone), ester (e.g., ethyl acetate), other non-aqueous solvents (e.g., dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 1-methyl-2-pyrrolidinone)), and water.

[0093] The composition may optionally 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 would be obvious to those skilled in the art.

[0094] A polymerizable ionic liquid containing "any" monomer may be prepared by any conventional free radical polymerization method, which includes solution, radiation, bulk, dispersion, emulsification, and suspension processes. The resulting (co)polymer may be random or block (co)polymer.

[0095] A useful initiator for preparing the (meth)acrylate adhesive copolymer used in the present invention is an initiator that generates free radicals that initiate the (co)polymerization of the monomer mixture upon exposure to heat. For preparing the (meth)acrylate polymer by emulsion polymerization, a water-soluble initiator is preferred. Suitable water-soluble initiators include, but are not limited to, potassium persulfate, ammonium persulfate, sodium persulfate, and mixtures thereof; redox initiators such as the 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 EIdu 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 included in 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 component in the pressure-sensitive adhesive.

[0096] Alternatively, the mixture can be polymerized by conventional techniques including, but not limited to, solvent polymerization, dispersion polymerization, and solvent-free bulk polymerization. The monomer mixture may contain a type and amount of polymerization initiator, particularly a thermal initiator or a photoinitiator, that is effective in polymerizing the comonomer, as previously described.

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

[0098] In a typical photopolymerization method, a monomer mixture can be irradiated with ultraviolet (UV) light in the presence of a photoinitiator (i.e., a photoinitiator). Preferred photoinitiators are available from Ciba Specialty Chemical Corp., Tarrytown, NY under trade names IRGACURE® and DAROCUR®, including 1-hydroxycyclohexylphenyl ketone (IRGACURE® 184) and 2,2-dimethoxy-1,2-diphenylethane-1-one (IRGACURE® 184). Examples include 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 (DAROCURE® 1173). Particularly preferred photoinitiators are IRGACURE® 819, 651, 184, and 2959.

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

[0100] Coating process Polymerizable ionic liquids can be applied to the surface of components (e.g., carriers, substrates, surface of articles, etc.) using various conventional coating methods. In some embodiments, the polymerizable ionic liquid, which contains any "any" monomer, is a pre-adhesive composition comprising 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, and foaming. The coating is optionally dried and cured at least partially, typically completely, using an energy source. In some embodiments, the pre-adhesive mixture contains 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 curing 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, more preferably less than 5% by weight, and most preferably less than 1% by weight of the cured composition.

[0102] In some embodiments, the thickness of the cured adhesive composition is at least 10 μm, at least 100 μm, at least 500 μm, or at least 1000 μm. In some embodiments, the thickness of the adhesive composition is up to 2 mm, up to 1000 μm, up to 500 μm, or up to 100 μm. In some embodiments, the thickness of the adhesive composition is 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 another embodiment, 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 opposite side of the carrier. The first and second polymerizable ionic liquids may be the same or different. Suitable carrier materials are described above.

[0104] Purpose The articles of this disclosure can offer 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., negative electrode), thus reducing the effort required to separate components within the article. Weakening of the adhesive bond increases with increasing DC potential (voltage), increasing the duration of the applied DC potential, or a combination thereof. Thus, the user can tailor the conditions for on-demand peeling to the application or need. For example, the user 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 1600 V / mm, up to 800 V / mm, up to 250 V / mm, or up to 90 V / 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 the application of the applied DC potential.

[0105] The articles of this disclosure also benefit from the properties and degree of ion content in the adhesive compositions. For example, polymerized ion content typically provides better adhesion than compositions containing the same ion content in unpolymerized (i.e., free) form, thus ensuring that components do not prematurely engage and detach during use. In some embodiments, the adhesive compositions of this disclosure exhibit 180° peel from glass at 12 inches / min (30.48 cm / min) as measured according to Test Method 1, 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.

[0106] Furthermore, higher levels of ion content in the adhesive composition can be achieved by polymerization of ionic liquids. In some embodiments, the adhesive composition contains 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%. Higher ion content has generally been found to improve adhesive peeling when a DC applied potential is applied. Weakening of the adhesive bond during peeling can be measured, for example, by the percentage change in adhesive work per surface area of ​​the two components bonded together in the adhesive composition. In some embodiments, the percentage change in adhesive work per surface area over 100 seconds at 0V and -25V 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 percentage change in the amount of adhesive work per unit surface area of ​​a component bonded to an article using the adhesive composition over 100 seconds at 0V and -25V is in the range of 10% to 100%, 10% to 99%, 40% to 99%, 60% to 99%, 70% to 99%, or 80% to 99%. In some embodiments, the applied DC potential is sufficient to completely detach the component from the article without user intervention.

[0107] Therefore, the components can be firmly bonded to each other using the adhesive composition and conveniently separated when a DC applied potential is applied. In some embodiments, the adhesive compositions of the present disclosure exhibit a 180° peel from glass of at least 0.5 N / cm at 12 inches / min (30.48 cm / min), and a % change in adhesive work per surface area of ​​at least 10% over 100 seconds at 0V and -25V.

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

[0109] The articles of this application can provide various 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 objects (e.g., components) used to perform various tasks. For example, the object may be a screwdriver or a soldering device. Once the task is complete, the object can be separated by applying an electric potential to the adhesive composition. In some embodiments, the separation may be designed so that the adhesive composition remains on the mechanical arm to grip a new and different object.

[0110] The articles of this application can be used, for example, in animal tracking collars, where researchers typically have to sedate the animals during both the application and removal of the collar. Using the articles of this application, it is possible to manufacture collars designed to fall off at the end of their lifecycle. For example, the collar can be secured around the animal's neck using an adhesive composition. A small battery used to collect tracking information may also be used near the end of the collection cycle to apply a potential across the adhesive composition, which then allows the adhesive to detach and the collar to fall to the ground. The collar can then be recovered by researchers using a tracking device.

[0111] In other applications, the goods can be used in the packaging and transportation industries. The adhesive composition can be used to bundle packages together. Upon arrival at the delivery destination, transportation workers 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 requiring periodic service or replacement. For example, a service panel may be bonded to a housing with an adhesive composition, and the panel may be removed by applying a DC applied potential to the adhesive composition. The panel can then be replaced after service, and in some embodiments, it may be repositioned using the same adhesive composition that was initially applied during manufacturing.

[0113] The article may also be a composite component product that has reached the end of its product lifecycle, and at least some, if not all, of its components are recyclable. If the components are bonded together by an adhesive composition, the recyclable components can be cleanly separated by applying a DC potential across the adhesive composition.

[0114] The uses described above are not intended to be limiting. The articles and methods of this application may find use in any variety of applications that benefit from on-demand adhesive removal. [Examples]

[0115] The objects and advantages of the present invention are further illustrated by the following embodiments, but the specific materials and their quantities, as well as other conditions and details described in these embodiments, should not be construed as unduly limiting the invention. These embodiments are for illustrative purposes only and are not intended to limit the scope of the appended claims.

[0116] Unless otherwise stated, all parts, percentages, ratios, etc., in the examples and elsewhere in this specification are based on 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 mixed until a coating viscosity of 0.3 milliwatts / cm² (mW / cm²) was achieved. 2 The material was placed in front of ultraviolet (UV) light with an intensity of 365 nanometers (nm) wavelength. A typical target viscosity for coating in this process is about 3000 centipoise (cP) at room temperature.

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

[0119] Preparation of single-layer transfer adhesive The pre-adhesion formulations of Comparative Examples C1-C6 and Examples E1-E6 were coated between silicone-treated PET release liners (RF02N / RF32N, available from SKC Haas (Seoul, South Korea)) with a wet coating weight of 0.15 mm. This structure was then subjected to a coating of approximately 950 millijoules / cm² (mJ / cm²). 2 It was cured using UV irradiation with a wavelength of 360 nm.

[0120] Preparation of a double-coated adhesive with a carrier layer The preparation of the double-coating adhesive on the nylon or tissue carrier layer was carried out in the same manner as the preparation of the single-layer transfer adhesive provided above, with the following exceptions: The pre-adhesive formulation of Example E5 was coated to a thickness of 0.05 mm between two silicone-treated PET liners and subjected to UV irradiation at a wavelength of 360 nm at approximately 950 mJ / cm². 2 The material was cured using [a specific method]. The top liner was removed, and a 0.05 mm layer of tissue or nylon material was laminated onto 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 the nylon or tissue side of the structure, and then subjected to UV irradiation at a wavelength of 360 nm at approximately 950 mJ / cm². 2 It was cured using [this method]. [Table 2]

[0121] Test Method 1: 180° peel adhesion strength Peel adhesion is the force required to remove a coated flexible sheet material from a test panel, measured at a specific angle and removal speed. In the embodiments of this 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 section of adhesive-coated sheet material, approximately 5 inches (12.7 cm) long, was cut, and one of the release liners was peeled from the coated adhesive. One side of a standard float glass test panel was cleaned using isopropanol and a lint-free wiper, and then the adhesive strip was applied to the clean side of the glass test panel. The strip was applied using a heavy rubber roller. 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 strength tester. The glass plate was then fixed to the platform of a mechanized instrument to move away from the scale at a controlled speed (12 inches / min) (30.48 cm / min). The peel test was started approximately one minute after applying the adhesive to the substrate. During the test, the scale reading in ounces was recorded as the average of both the peak force and the minimum force during peeling. Three peel tests were performed for each example, and the average value was calculated to obtain the peel adhesive strength. The results are summarized in Table 3.

[0122] During the peel-and-adhesion strength test, the failure mode was also recorded for each example, and the results are further summarized in Table 3. "ad" indicates adhesive failure from the substrate, and "co" indicates cohesive failure of the adhesive material.

[0123] Test Method 2: Bonding work per unit surface area with and without applied potential. The amount of bonding work per surface area required to separate two parallel bonded test surfaces was measured while separating the surfaces in the thickness direction of the bonding material at a specific removal rate.

[0124] The bonding work per square centimeter of surface area is expressed by multiplying the Newtons per square centimeter of the bonded surface by the distance traveled between the plates (in centimeters, in N / cm units). This is calculated by integrating the area under the curve of the tensile force in Newtons (N) plotted against the change in the gap between bonded surfaces in centimeters (cm units), and then multiplying this value by the area under the bonded test surface in square centimeters (cm units). 2 The analysis was performed by dividing by the initial contact area per unit.

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

[0126] For each test, an 8mm diameter parallel plate fixture was mounted on the rheometer, and the gap between the plates was made zero. 8mm diameter discs were cut from single-layer transfer adhesives (C1-C6 and E1-E6) or double-coating adhesives (E7 and E8). One of the release liners was peeled from the disc, and the exposed adhesive was applied to a clean, 8mm diameter stainless steel plate-shaped surface at the bottom of the rheometer. A second release liner was peeled from the coated adhesive. The temperature was equilibrated at 25°C for 1 minute. Next, the upper plate was lowered and compressed in contact with the adhesive for 500 seconds with a compressive load of 5N. During the compression process, a DC potential was applied at either 0V DC (as a control test) or -25V DC during the last 100 seconds of compression loading. At the end of the compression load, the plates were separated at a speed of 0.001 cm / sec, and the tensile force required to separate the plates was measured as a function of the plate separation distance. Three tests were conducted for each condition in each example, and the average values ​​for adhesive work per surface area, summarized in Table 3, were obtained.

[0127] The reduction rate (%) of adhesive work per unit surface area was calculated by subtracting the respective average values ​​at a DC applied potential of -25V from the corresponding average values ​​without applied voltage, and then dividing the difference by the value without applied voltage. A positive reduction rate indicates a reduction in adhesive work per unit surface area after the application of a DC potential of -25V. These reduction rate values ​​for each example are summarized in Table 3.

[0128] In the tested examples, a negative DC potential resulted in preferential delamination from the upper plate, while a positive DC potential resulted in preferential delamination from the lower (ground) plate.

[0129] The tensile adhesive strength profile for Example E4 is shown in Figure 3. The test was performed at DC potentials of 0V and -25V applied during the last 100 seconds of the compression process. 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 speed of 0.01 mm / sec is plotted on the x-axis. The application of potential reduces the bonding strength of the adhesive, as indicated by the reduction in the bonding work (explained by the area under the curve). [Table 3]

[0130] Figure 4 shows a contour surface plot of the bonding work per unit surface area (shown by grayscale) from the tensile bonding test of Example E2 as a function of the applied DC voltage (y-axis) and the duration of voltage application before separating the plates (x-axis).

[0131] Accordingly, this disclosure provides, in particular, articles containing adhesive compositions exhibiting on-demand peel behavior. Various features and advantages of this disclosure are described in the following claims. The present invention encompasses the following embodiments. (1) A first component having a first conductive surface, A second component having a second surface, An adhesive composition disposed between the first conductive surface and the second surface, 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 adhesive work per unit surface area, is reduced by applying a DC potential across the adhesive composition. The polymerizable ionic liquid is Polymerizable anions and imidazole compounds of formula I [ka] (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R 1 is H or C 1 ~C 25 It is an alkyl group, R 2 is H or -CO-X1 -R 5 And R 5 is H or C 1 ~C 25 It is an alkyl group, X 1 -O- or -NR 6 - and R 6 is H or C 1 ~C 6 It is alkyl, R 3 is H or CH 3 It is preferably H, R 8 is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R 1 and R 2 (is H) An article comprising a cation corresponding to the conjugate acid of a given acid. (2)R 1 H is R 2 H is R 3 The article described in item 1, wherein w is H, w is 0, and Z is an ester. (3) Z is -C(O)-OR 10 And R 10 The article according to item 2, wherein is a hydrocarbyl group, and the hydrocarbyl is optionally substituted with a hydroxyl group. (4) The polymerizable anion comprises an ethylenically unsaturated polymerizable group and a carboxylic acid group (-COOH) and a sulfonic acid group (-SO 3 H), sulfate group (-SO 4 H), phosphonic acid group (-PO 3 H 2 ), phosphate group (-OPO 3 Articles according to any of items 1 to 3, comprising H) or an acidic group selected from these salts. (5) The article according to item 4, wherein the polymerizable anion comprises an ethylenically unsaturated polymerizable group and a carboxylic acid group (-COOH). (6) The polymerizable ionic liquid further comprises any monomer component, and the amount of the monomer component is determined based on the total weight of the monomer components. i. 60% to 99.5% by weight of (meth)acrylic acid ester monomer, ii. 0% to 30% by weight of non-acidic functional ethylenically unsaturated polar monomers, iii.0% to 20% by weight of polyfunctional (meth)acrylates, The items listed in any of items 1-5, including the items listed in item 1-5. (7) The article according to item 6, 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 any monomer component. (8) The article according to item 7, wherein the polymerizable ionic liquid further comprises a photoinitiator. (9) The article according to any one of items 1 to 8, wherein the first component comprises a first nonconductive material and a first conductive coating for providing the first conductive surface. (10) The article according to any one of items 1 to 9, wherein the second surface of the second component is a second conductive surface. (11) The article according to item 10, wherein the second component comprises a second nonconductive material and a second conductive coating for providing the second conductive surface. (12) The article according to item 10 or 11, wherein the first conductive surface and the second conductive surface are each selected from the group consisting of metals, mixed metals, alloys, metal oxides, composite metals, conductive plastics, conductive polymers, or combinations thereof. (13) An article according to any one of items 10 to 12, wherein the composition of the first conductive surface is different from the composition of the second conductive surface. (14) An article according to any one of items 10 to 12, wherein the composition of the first conductive surface is the same as the composition of the second conductive surface. (15) The adhesive composition A carrier having a first main surface and a second main surface opposite to the first main surface, A first adhesive composition comprising a cured first polymerizable ionic liquid on the first main surface of the carrier, A second adhesive composition comprising a cured second polymerizable ionic liquid on the second main surface of the carrier, It is a double-sided adhesive that includes The surface of the first adhesive composition opposite to the carrier is in contact with the first conductive surface of the first component. The surface of the second adhesive composition opposite to the carrier is in contact with the second surface of the second component. Each of the first and second polymerizable ionic liquids is Polymerizable anions and imidazole compounds of formula I

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Claims

1. A first component having a first conductive surface, A second component having a second surface, An adhesive composition disposed between the first conductive surface and the second surface, 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 adhesive work per unit surface area, is reduced by applying a DC potential across the adhesive composition. The polymerizable ionic liquid is Polymerizable anions and imidazole compounds of formula I 【Chemistry 1】 (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R １ is H or C １ ~C ２５ It is an alkyl group, R ２ represents H or -CO-X １ -R ５ , and R ５ represents H or C １ -C ２５ alkyl group, X １ represents -O- or -NR ６ -, and R ６ represents H or C １ -C ６ alkyl, and R ３ is H or CH ３ And, R ８ w is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R １ and R ２ (is H) An article comprising a cation corresponding to the conjugate acid of a given acid.

2. R １ H is R ２ H is R ３ H is , w is 0, and Z is -C(O)-O-R １０ And R １０ The article according to claim 1, wherein the group is a hydrocarbyl group which may be substituted with a hydroxyl group.

3. The polymerizable anion comprises an ethylenically unsaturated polymerizable group and a carboxylic acid group (-COOH) and a sulfonic acid group (-SO). ３ H), sulfate group (-SO ４ H), phosphonic acid group (-PO ３ H ２ ), phosphate group (-OPO ３ The article according to claim 1, comprising H), or an acidic group selected from salts thereof.

4. The polymerizable ionic liquid further comprises an arbitrary monomer component, and the arbitrary monomer component is determined based on the total weight of the arbitrary monomer components. i. 60% to 99.5% by weight of (meth)acrylic acid ester monomer, ii. 0% to 30% by weight of non-acidic functional ethylenically unsaturated polar monomers, iii. 0% to 20% by weight of polyfunctional (meth)acrylates, The article according to 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 any monomer component.

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

6. The adhesive composition A carrier having a first main surface and a second main surface opposite to the first main surface, A first adhesive composition comprising a cured first polymerizable ionic liquid on the first main surface of the carrier, A second adhesive composition comprising a cured second polymerizable ionic liquid on the second main surface of the carrier, It is a double-sided adhesive that includes The surface of the first adhesive composition opposite to the carrier is in contact with the first conductive surface of the first component. The surface of the second adhesive composition opposite to the carrier is in contact with the second surface of the second component. Each of the first and second polymerizable ionic liquids is, Polymerizable anions and imidazole compounds of formula I 【Chemistry 2】 (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R １ is H or C １ ~C ２５ It is an alkyl group, R ２ is H or -CO-X １ -R ５ And R ５ is H or C １ ~C ２５ It is an alkyl group, X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ It is alkyl, R ３ is H or CH ３ And, R ８ w is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R １ and R ２ (is H) The article according to claim 5, comprising a cation corresponding to the conjugate acid of the

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

8. The article according to 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 main surface and a second main surface opposite to the first main surface, A first adhesive composition comprising a cured first polymerizable ionic liquid on the first main surface of the carrier, A second adhesive composition comprising a cured second polymerizable ionic liquid on the second main surface of the carrier, It is a double-sided adhesive that includes The surface of the first adhesive composition opposite to the carrier is in contact with the first conductive surface of the first component. The surface of the second adhesive composition opposite to the carrier is in contact with the second surface of the second component. The carrier is conductive, Each of the first and second polymerizable ionic liquids is, Polymerizable anions and imidazole compounds of formula I 【Transformation 3】 (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R １ is H or C １ ~C ２５ It is an alkyl group, R ２ is H or -CO-X １ -R ５ And R ５ is H or C １ ~C ２５ It is an alkyl group, X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ It is alkyl, R ３ is H or CH ３ And, R ８ w is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R １ and R ２ (is H) The article according to claim 1, comprising a cation corresponding to the conjugate acid of the same.

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

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

12. The article according to claim 1, wherein the effort required to separate the first component from the second component is at least 20%, when measured by the percentage change in the amount of adhesive work per unit surface area over 100 seconds at 0V and -25V.

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

14. The method according to 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, and the method further comprises applying a DC potential to detach the adhesive composition from the negative electrode, thereby causing the first component to separate from the second component.

15. The adhesive composition A carrier having a first main surface and a second main surface opposite to the first main surface, A first adhesive composition comprising a cured first polymerizable ionic liquid on the first main surface of the carrier, A second adhesive composition comprising a cured second polymerizable ionic liquid on the second main surface of the carrier, It is a double-sided adhesive that includes The surface of the first adhesive composition opposite to the carrier is in contact with the first conductive surface of the first component. The surface of the second adhesive composition opposite to the carrier is in contact with the second surface of the second component. The carrier is conductive, The first conductive surface or carrier functions as a negative electrode, and the other of the first conductive surface or carrier functions as a positive electrode. Each of the first and second polymerizable ionic liquids is, Polymerizable anions and imidazole compounds of formula I 【Chemistry 4】 (In the formula, Z contains a ketone, ester, amide, nitrile, or azulactone functional group. R １ is H or C １ ~C ２５ It is an alkyl group, R ２ is H or -CO-X １ -R ５ And R ５ is H or C １ ~C ２５ It is an alkyl group, X １ is -O- or -NR ６ - and R ６ is H or C １ ~C ６ It is alkyl, R ３ is H or CH ３ And, R ８ w is a (hetero)hydrocarbyl group which may be substituted at the 2nd, 4th, or 5th position, and w is 0, 1, 2, or 3. However, if Z contains a nitrile or azulactone functional group, R １ and R ２ (is H) It contains a cation corresponding to the conjugate acid of, The method according to claim 13, further comprising applying a DC potential to detach the adhesive composition from the negative electrode and causing the first component to separate from the second component.

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