阅读说明：本技术 咪唑鎓氟磺酰亚胺离子粘合剂组合物及其选择性脱粘 (Imidazolium fluorosulfonylimide ionic binder compositions and selective debonding thereof ) 是由 史丹尼斯劳·瑞瓦尔 汀莎·姚 胡毓芬 张洪喜 王鹏 于 2018-11-20 设计创作，主要内容包括：粘合剂可包含至少一种式1的咪唑鎓阳离子和至少一种式2的氟磺酰亚胺阴离子。在这些式中：R<Sup>1</Sup>为氢,C<Sub>1</Sub>-C<Sub>3</Sub>烷基或任选取代的C<Sub>1</Sub>-C<Sub>12</Sub>烷基胺,R<Sup>3</Sup>各自独立地为C<Sub>1</Sub>-C<Sub>3</Sub>烷基或任选取代的C<Sub>1</Sub>-C<Sub>12</Sub>烷基胺,且R<Sup>2</Sup>、R<Sup>4</Sup>、R<Sup>5</Sup>各自独立地为氢或C<Sub>1</Sub>-C<Sub>3</Sub>烷基；<Image he="267" wi="700" file="DDA0002589090220000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The binder may comprise at least one imidazolium cation of formula 1 and at least one fluorosulfonylimide anion of formula 2. In these formulae: r 1 Is hydrogen, C 1 ‑C 3 Alkyl or optionally substituted C 1 ‑C 12 Alkylamines, R 3 Each independently is C 1 ‑C 3 Alkyl or optionally substituted C 1 ‑C 12 Alkylamine, and R 2 、R 4 、R 5 Each independently is hydrogen or C 1 ‑C 3 An alkyl group;)

1. An adhesive composition comprising:

at least one imidazolium cation of formula 1 and/or formula 3:

wherein:

R¹is hydrogen, C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine;

R³is C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine;

R²、R⁴、R⁵、R⁶and/or R⁷Each independently is hydrogen or C₁-C₃An alkyl group;

y is a linking group; and

at least one fluorosulfonylimide anion of formula 2 and/or formula 4:

wherein:

each R is⁸Are each hydrogen or fluorine; and is

n is an integer.

2. An adhesive composition comprising:

at least one imidazolium cation of formula 1:

wherein:

R¹is hydrogen, C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine;

R³is C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; and is

R²、R⁴、R⁵Each independently is hydrogen or C₁-C₃An alkyl group; and

at least one fluorosulfonylimide anion of formula 2:

3. the adhesive composition of claim 1 or 2, wherein:

R¹、R²、R⁴and R⁵Each independently hydrogen, methyl, ethyl or propyl;

y is C₁-C₁₂An alkyl group; and is

n is 0, 1,2, 3 or 4.

4. The adhesive composition of claim 1 or 2, wherein R¹Or R³At least one of which is as follows:

5. the adhesive composition of claim 1 or 2, wherein the imidazolium cation is at least one of the following:

6. the adhesive composition of claim 1,2, 3 or 4 wherein R²Is ethyl.

7. The adhesive composition of claim 1 or 2, further comprising a polymer containing an imidazolium cation and a fluorosulfonylimide anion.

8. The adhesive composition of claim 7, wherein the polymer comprises at least one polymer selected from an acrylate polymer, an alkyl-alkyl acrylate polymer, or a combination thereof.

9. The adhesive composition of claim 8, wherein the polymer comprises an acrylate polymer, a methacrylate polymer, or a combination of both an acrylate polymer and a methacrylate polymer.

10. The adhesive composition of claim 9, wherein the polymer comprises acrylic acid, acrylic acid C_1-14Alkyl esters, methacrylic acid C_1-14A hydrocarbyl ester monomer, or a combination thereof.

11. The adhesive composition of claim 7, 8, 9 or 10 wherein the polymer is crosslinked.

12. The adhesive composition of claim 11 wherein the polymer is crosslinked with an epoxy crosslinking agent.

13. The adhesive composition of claim 12, wherein the epoxy crosslinker is N, N' -tetraglycidyl-m-xylylenediamine.

14. The adhesive composition of claim 1 or 2, wherein the imidazolium cation and the fluorosulfonylimide anion are present in a ratio of about 1: 1.

15. The adhesive composition of any one of claims 1-13 wherein the adhesive composition is configured to be selectively debondable.

16. The adhesive composition of claim 14, wherein the adhesive composition is configured to be selectively debondable upon application of an electromotive force.

17. A method of making the adhesive composition of claim 1 or 2, the method comprising:

the fluorosulfonylimide anion is combined with an imidazolium cation.

18. The method of claim 17, further comprising combining a fluorosulfonylimide anion and an imidazolium cation with the polymer.

19. The method of claim 18, further comprising crosslinking the polymer before, during, or after combining with the fluorosulfonylimide anion and the imidazolium cation.

20. A method of adhering the adhesive composition of claim 1 or 2 to a substrate, the method comprising:

the adhesive composition is applied to a first conductive substrate.

21. The method of claim 20, further comprising applying the adhesive composition to a second conductive substrate such that the adhesive composition is between the first conductive substrate and the second conductive substrate.

22. An adhesive member, comprising:

an adhesive layer formed of the adhesive composition of claim 1 or 2;

at least one release liner on at least one side of the adhesive layer.

23. The adhesive member of claim 22 comprising a release liner on each side of the adhesive layer.

24. A selective adhesive material comprising the adhesive composition of claim 1,2, 3,4,5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16, wherein application of an electromotive force to the selective adhesive material reduces adhesion of the selective adhesive material.

25. A selectively debondable structure comprising a selectively debondable layer of the selective adhesive material of claim 24, wherein the selectively debondable layer is disposed between a first conductive surface and a second conductive surface.

26. The selectively debondable structure of claim 25 wherein the selective adhesive material adheres to the first conductive surface and the second conductive surface.

27. The selectively debondable structure of claim 25 or 26 further comprising a power source in electrical communication with at least one of the first conductive surface and the second conductive surface, thereby creating a closable electrical circuit.

28. The selectively debondable structure of claim 25, 26, or 27 wherein the first conductive surface comprises a conductive material.

29. The selectively debondable structure of claim 25, 26, 27 or 28 wherein the second conductive surface comprises a conductive material.

30. The selectively debondable structure of claim 28 or 29 wherein the electrically conductive material comprises a metal, a mixed metal, an alloy, a metal oxide, a composite metal, an electrically conductive plastic, or an electrically conductive polymer.

31. The selectively debondable structure of claim 30 wherein the electrically conductive material comprises an electrically conductive metal.

32. The selectively debondable structure of claim 31 wherein the conductive metal comprises aluminum.

33. A selectively debondable structure according to claim 25, 26, 27, 28, 29, 30, 31, or 32 wherein the selective adhesive material has a reduced corrosive effect on the first and second electrically conductive surfaces.

34. A selectively debondable structure comprising a selectively debondable layer of the selective adhesive material of claim 24, wherein the selectively debondable layer is disposed on the first electrically conductive surface.

The technical field is as follows:

the present disclosure relates to compounds and/or materials for use as adhesives and coatings for application to surfaces, wherein the adhesives and coatings can be debonded from the surface without damage to the surface upon application of an electromotive force. The disclosure also relates to methods of debonding adhesives and coatings from surfaces. More particularly, the present disclosure relates to cationic imidazolium and anionic fluorosulfonyl imide compositions for adhesives and coatings.

Background

Summary of The Invention

In some embodiments, the adhesive composition may comprise: at least one imidazolium cation of formula 1 and/or formula 3:

wherein: r¹Is hydrogen, C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; r³Is C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; r²、R⁴、R⁵、R⁶And/or R⁷Each independently is hydrogen or C₁-C₃An alkyl group; y is a linking group.

The adhesive composition may further comprise at least one disulfonimide anion of formula 2 and/or formula 4:

wherein: each R⁸Are each hydrogen or fluorine; and n is an integer.

In some embodiments, the adhesive composition may comprise: at least one imidazolium cation of formula 1:

wherein: r¹Is hydrogen, C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; r³Is C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; r²、R⁴、R⁵Each independently is hydrogen or C₁-C₃An alkyl group.

The adhesive composition may further comprise at least one fluorosulfonylimide anion of formula 2:

in some embodiments, the adhesive composition may be defined by: r¹、R²、R⁴And R⁵Each independently hydrogen, methyl, ethyl or propyl; y is substituted or unsubstituted C, with or without hetero atoms₁-C₁₂An alkyl group; n is 0, 1,2, 3 or 4.

In some embodiments, the adhesive composition may be defined by: wherein R is¹Or R³At least one of the following:

in some embodiments, the imidazolium cation is at least one of the following:

in some embodiments, R²Is methyl, ethyl or propyl, of which ethyl may be an example.

In some embodiments, the adhesive composition of one of the embodiments may comprise a polymer comprising an imidazolium cation and a fluorosulfonylimide anion. In some aspects, the polymer comprises at least one polymer selected from an acrylate polymer, an alkyl-alkyl acrylate polymer, or a combination thereof. In some aspects, the polymer comprises an acrylate polymer, a methacrylate polymer, or a combination of both an acrylate polymer and a methacrylate polymer. In some aspects, the polymer comprises acrylic acid, acrylic acid C_1-14Alkyl esters, methacrylic acid C_1-14A hydrocarbyl ester monomer, or a combination thereof. In some aspects, the polymer is crosslinked. In some aspects, the polymer is crosslinked with an epoxy crosslinking agent. In some aspects, the epoxy crosslinker is N, N' -tetraglycidyl-m-xylylenediamine.

In some embodiments, the imidazolium cation and fluorosulfonylimide anion are present in a ratio of about 1: 1.

In some embodiments, the adhesive composition is configured to be selectively debondable. In some aspects, the adhesive composition is configured to be selectively debondable upon application of an electromotive force.

In some embodiments, a method of making an adhesive composition of one of the embodiments comprises: the fluorosulfonylimide anion is combined with an imidazolium cation. In some aspects, the method can include combining a fluorosulfonylimide anion and an imidazolium cation with a polymer. In some aspects, the method can include crosslinking the polymer before, during, or after combination with the fluorosulfonylimide anion and the imidazolium cation.

In some embodiments, a method of adhering the adhesive composition of one of the embodiments to a substrate may comprise: the adhesive composition is applied to a first conductive substrate. In some aspects, the method can further include applying the adhesive composition to a second conductive substrate such that the adhesive composition is between the first conductive substrate and the second conductive substrate.

In some embodiments, the adhesive member may comprise: an adhesive layer formed of the adhesive composition of one of the embodiments; and at least one release liner on at least one side of the adhesive layer. In some aspects, the adhesive member may comprise a release liner on each side of the adhesive layer.

In some embodiments, the selective adhesive material may comprise an adhesive composition of one of the embodiments configured such that application of an electromotive force to the selective adhesive material reduces adhesion of the selective adhesive material.

In some embodiments, a selectively debondable structure may comprise a selectively debonding layer of the selective adhesive material of one of the embodiments, wherein the selectively debonding layer is disposed between the first conductive surface and the second conductive surface. In some aspects, the selective adhesive material adheres to the first conductive surface and the second conductive surface. In some aspects, the selectively debondable structure of one of the embodiments may comprise a power source in electrical communication with at least one of the first conductive surface and the second conductive surface, thereby creating a closable electrical circuit therewith. In some aspects, the power supply is a DC power supply, which can provide about 3 volts to about 100 volts. In some aspects, the selectively debondable structure of one of the embodiments may comprise a first conductive surface comprising a conductive material, which may be configured as a substrate. In some aspects, the selectively debondable structure of one of the embodiments may comprise a second conductive surface comprising a conductive material, which may be configured as a substrate. In some aspects, the conductive material comprises a metal, a mixed metal, an alloy, a metal oxide, a composite metal, a conductive plastic, or a conductive polymer. In some aspects, the conductive material comprises a conductive metal, a mixed metal, an alloy, a metal oxide, a mixed metal oxide, a conductive plastic, a carbonaceous material, a composite metal, or a conductive polymer. In some aspects, the conductive material comprises a conductive metal. In some aspects, the conductive metal comprises aluminum. In some aspects, the selective adhesive material has a reduced corrosive effect on the first conductive surface and/or the second conductive surface.

In some embodiments, a selectively debondable structure may comprise a selectively debondable layer of the selective adhesive material of one of the embodiments, wherein the selectively debondable layer is disposed on the first conductive surface. In some aspects, the selectively debondable structure of one of the embodiments may comprise a power source in electrical communication with the first conductive surface.

In some embodiments, the selectively debondable material may comprise the ionic composition and/or the adhesive composition of one of the embodiments. In some aspects, the selective debonding material may comprise a polymer. In some aspects, the polymer may comprise an acrylate polymer, a methacrylate polymer, or a combination of both an acrylate polymer and a methacrylate polymer. In some aspects, the polymer may comprise acrylic acid, acrylic acid C_1-14Alkyl esters or methacrylic acid C_1-14A hydrocarbyl ester monomer. In some aspects, the selectively debonding material is an adhesive.

The foregoing summary of the invention is illustrative only and is not intended to be in any way limiting. In addition to the illustrative aspects, embodiments, and features described above, further aspects, embodiments, and features will become apparent by reference to the drawings and the following detailed description.

Brief description of the drawings

The above and below information and other features of the present disclosure will become more apparent from the following description and appended claims, taken in conjunction with the accompanying drawings. Understanding that these drawings depict only several embodiments in accordance with the disclosure and are, therefore, not to be considered limiting of its scope, the disclosure will be described with additional specificity and detail through use of the accompanying drawings.

FIG. 1 is a schematic view of an apparatus containing one embodiment of the ionic compositions described herein.

Fig. 2 is a schematic view of an apparatus containing one embodiment of the ionic compositions described herein.

Fig. 3 is a schematic of an apparatus used in the adhesion quality test of one embodiment of the ionic compositions described herein.

FIG. 4 is a plot of peel strength density versus time for one embodiment of the compounds described herein tested in the apparatus shown in FIG. 3.

The elements and components of the drawings may be arranged in accordance with at least one of the embodiments described herein, and the arrangement may be modified by one of ordinary skill in the art in light of the disclosure provided herein.

Detailed Description

In the following detailed description, reference is made to the accompanying drawings, which form a part hereof. In the drawings, like numerals generally identify like components, unless context dictates otherwise. The illustrative embodiments described in the detailed description, drawings, and claims are not intended to be limiting. Other embodiments may be utilized, and other changes may be made, without departing from the spirit or scope of the subject matter presented herein. It is easy to understand that: the various aspects of the disclosure, as generally described herein, and illustrated in the figures, may be arranged, substituted, combined, separated, and designed in a wide variety of different configurations, all of which are explicitly contemplated herein.

In general, the present techniques include compounds and/or materials that are used as adhesives and coatings applied to surfaces, where the adhesives and coatings can be debonded from the surface without damaging the surface upon application of an electromotive force. The present technology also includes methods and systems for debonding adhesives and coatings from a substrate surface. Additionally, the present technology includes cationic imidazolium and anionic sulfonimide compositions for adhesives and coatings.

In some embodiments, the ionic compositions described herein can be used to adhere to a surface. In some aspects, the ionic composition can be configured as an adhesive or coating for a surface, which when adhered to the surface, the adhesive or coating on the surface can be removed from the surface by a debonding procedure. The ionic composition is configured such that, after bonding to a surface, it can be removed without damaging the surface. This may be advantageous to allow the adhesive or coating to be removed from the surface to keep the surface in an original state. The debonding procedure may include applying electrical energy (e.g., via an electromotive force) to cause the adhesive or coating to lift from the surface without damaging the surface.

Additionally, the ionic compositions described herein can be configured such that they are substantially less corrosive to metal substrates than previous ionic compositions. The ionic composition can now be applied to the metal surface of a substrate without causing corrosion of the substrate. This may provide substantial benefits by: allowing more types of surfaces (e.g., on metal substrates) to receive ionic compositions as adhesives or coatings that can be selectively debonded while at the same time reducing corrosion compared to existing compositions.

In some embodiments, the ionic composition may comprise an imidazolium cation, which includes an imidazole core structure, and thus may be referred to as an imidazole or an imidazolium, which may or may not be substituted. The imidazolium cation of the ionic composition can include a structure represented by formula 1 below:

the structure of formula 1 may include any substituent R group for R¹、R²、R³、R⁴And/or R⁵Such as those described herein or otherwise known.

With respect to any relevant structural representation, such as formula 1, in some embodiments, R is¹Is H, C₁-C₃Alkyl (e.g. methyl, ethyl, propyl, isopropyl, etc.) or optionally substituted C₁-C₁₂An alkyl amine. In some embodiments, R¹Is C₁An alkyl group. In some embodiments, R¹Is 1- (2- (diisopropylamino) ethyl).

With respect to any relevant structural representation, such as formula 1, in some embodiments, R is²Is H or C₁-C₃Alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, etc.). In some embodiments, R²Is H. In some embodiments, R²Is C₂An alkyl group.

With respect to any relevant structural representation, such as formula 1, in some embodiments, R is³Is C₁-C₃Alkyl (e.g. methyl, ethyl, propyl, isopropyl, etc.) or optionally substituted C₁-C₁₂An alkyl amine. In some embodiments, R³Is 1- (2- (diisopropylamino) ethyl).

With respect to any relevant structural representation, such as formula 1, in some embodiments, R is⁴Is H or C₁-C₃Alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, etc.). In some embodiments, R⁴Is H.

In some embodiments of formula 1, the R group can be defined as follows: r¹Can be hydrogen or C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkylamine; r²、R⁴And R⁵May each independently be hydrogen or C₁-C₃An alkyl group; r³May be C₁-C₃Alkyl or optionally substituted C₁-C₁₂An alkyl amine.

In one example, the ion under formula 1The composition may comprise: r¹Is C₁An alkyl group; r²Is hydrogen; r³Is 1- (2- (diisopropylamino) ethyl); r⁴And R⁵Are all hydrogen.

In another example, an ionic composition under formula 1 can include: r¹Is 1- (2- (diisopropylamino) ethyl); r²Is C₂An alkyl group; r³Is 1- (2- (diisopropylamino) ethyl); r⁴And R⁵Are all hydrogen.

In some embodiments, R¹、R²、R³、R⁴And/or R⁵The substituents may each independently include a hydrophilic functional group. In some embodiments, R¹、R²And R³At least one of the substituents may include a hydrophilic functional group. In some embodiments, the hydrophilic functional group can comprise nitrogen, sulfur, and/or phosphorus. In some embodiments, the hydrophilic functional group can comprise an amino group. In some aspects, R¹、R²And/or R³The substituents may each independently include a hydrophilic functional group. In some aspects, R¹And/or R³The substituents may each independently include a hydrophilic functional group.

In some embodiments, R¹、R²、R³、R⁴And/or R⁵The substituents may each independently comprise a hydrophilic functional group comprising one or more of: amino, mono (alkyl) substituted amino and di (alkyl) substituted amino, mono (aryl) substituted amino and di (aryl) substituted amino, alkylamido, arylamido, imino, alkylimino, arylimino, nitro, nitroso, sulfo, sulfonate, alkylsulfanyl, arylsulfanyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, phosphonyl, phosphonato, phosphinato, phospho, phosphino, hydroxyl, and combinations thereof, which may further comprise at least one C coupled thereto₁-C₃An alkyl group, a carboxyl group,to form hydrophilic functional groups. In some embodiments, R¹、R²And R³At least one of the substituents may include a hydrophilic functional group. In some aspects, R¹、R²And/or R³The substituents may each independently include a hydrophilic functional group. In some aspects, R¹And/or R³The substituents may each independently include a hydrophilic functional group.

In some embodiments, R¹、R²、R³、R⁴And/or R⁵The substituents may each independently include a hydrophobic functional group. In some embodiments, R¹、R²And R³At least one of the substituents may include a hydrophobic functional group. In some embodiments, the hydrophobic functional group may comprise an optionally substituted alkyl group. In some embodiments, the optionally substituted alkyl group may comprise a methyl group, an ethyl group, and/or a propyl group. In some aspects, R¹、R²And/or R³The substituents may each independently include a hydrophobic functional group. In some aspects, R¹And/or R³The substituents may each independently include a hydrophobic functional group. In some aspects, R²The substituent may include a hydrophobic functional group.

In some embodiments, the imidazolium cation may comprise a first amine as one or more substituents. In some embodiments, the first amine may be an aliphatic amine. In some embodiments, the aliphatic amine can have two substituents, such as an R group (e.g., R) as defined herein⁶And/or R⁷). In some embodiments, the aliphatic amine may comprise an amino group.

In some embodiments, the imidazolium cation can include a second amine in addition to the first amine. In some embodiments, the second amine may comprise an aromatic amine. In some embodiments, the arylamine may have two substituents, which may be R¹、R²、R³、R⁴And/or R⁵At least two of (1), preferably R¹And R²As a complement to the first amine on one of the other R groups. In some embodiments, arylThe amine may be an imidazolium group. In some embodiments, the imidazolium groups may be present only at R¹、R²And R³Wherein R includes a substituent group⁴And R⁵Is hydrogen.

In some embodiments, R¹And/or R³Alkyl groups such as methyl, ethyl or propyl may be included.

In some embodiments, R¹And/or R³The following substituents may be contained:

in some embodiments, R²Alkyl groups such as methyl, ethyl or propyl may be included.

In some embodiments, the imidazolium cation may be selected from the following structures:

in some embodiments, the ionic composition can have one or more different types of imidazolium cations, such as one or both of the aforementioned structures.

In some embodiments, the ionic composition may comprise a sulfonyl imide sulfonate anion. In some embodiments, the sulfonyl sulfonimide anion can comprise a fluoroalkyl sulfonimide compound (e.g., CH)₂FSO₂NSO₂CH₂F，CF₃SO₂NSO₂CF₃Etc.). In some embodiments, the sulfonyl imide sulfonate anion may comprise a fluorosulfonimide compound.

Thus, the ionic composition may also comprise a sulfonimide anion. The sulfonimide anion may include a structure as shown in formula 2 below:

in some embodiments, the ionic composition can comprise an imidazolium cation and a sulfonimide anion.

In some embodiments, the ionic composition may comprise a cation having an imidazolium attached to an amino group through a linking group, which may be referred to as an imidazolium amino (imidazolium amino). The imidazolium amino cation of the ionic composition can include a structure represented by formula 3 below:

the structure of formula 3 may comprise any substituted R group for R₁、R₂、R₄、R₅、R₆And/or R₇Such as those described in formula 1 or those described herein or other known ones.

In some embodiments of formula 3, the R group can be defined as follows: r¹Can be hydrogen or C₁-C₃Alkyl (e.g. methyl, ethyl, propyl, isopropyl, etc.) or optionally substituted C₁-C₁₂An alkylamine; r²、R⁴、R⁵、R⁶And/or R⁷May each independently be hydrogen or C₁-C₃Alkyl (e.g., methyl, ethyl, propyl, isopropyl, etc.); and Y may be a linking group.

In some embodiments, Y is a linking group, which represents a bond between nitrogen atoms or represents a chain having one or more chain atoms. In some embodiments, Y is a linking group having at least one chain atom. When Y is a chain atom or more than one chain atom, there may be R as defined herein on one or more of the chain atoms⁷And (4) a substituent. The linking group may be a hydrocarbon chain with or without one or more heteroatoms such as O, N or S. The linking group can comprise a straight-chain aliphatic, branched-chain aliphatic, cyclic aliphatic, substituted aliphatic, unsubstituted aliphatic, saturated aliphatic, unsaturated aliphatic, aromatic, polyaromatic, substituted aromatic, heteroaromatic, amines (amines), primary, secondary, tertiary, aliphatic, carbonyl, carboxyl, and the likeAmides, esters, amino acids, polymers, peptides, polypeptides and substituted or unsubstituted derivatives thereof, or combinations thereof. In some aspects, the linking group can comprise C₁-C₂₄Alkyl radical, C₂-C₂₄Alkenyl radical, C₂-C₂₄Alkynyl, C₆-C₂₀Aryl radical, C₇-C₂₄Alkylaryl group, C₇-C₂₄Aralkyl, amino, mono (alkyl) and di (alkyl) substituted amino, mono (aryl) and di (aryl) substituted amino, alkylamido, arylamido, imino, alkylimino, arylimino, nitro, nitroso, sulfo, sulfonate, alkylsulfanyl (alkylsulfanyl), arylsulfanyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, phosphono, phosphinic, phospho, phosphino, and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₁₂Alkyl radical, C₂-C₁₂Alkenyl or C₂-C₁₂Alkynyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₁₀Alkyl radical, C₂-C₁₀Alkenyl or C₂-C₁₀Alkynyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₈Alkyl radical, C₂-C₈Alkenyl or C₂-C₈Alkynyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₆Alkyl radical, C₂-C₆Alkenyl or C₂-C₆Alkynyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₄Alkyl radical, C₂-C₄Alkenyl or C₂-C₄Alkynyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group canComprises C₁-C₃Alkyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof. In some aspects, the linking group can comprise C₁-C₂Alkyl groups and any derivatives thereof with or without heteroatoms, and combinations thereof.

In some embodiments, the imidazolium salt cation may comprise a first amine as one or more of the substituents. In some embodiments, the first amine can be an aliphatic amine. In some embodiments, the aliphatic amine may have two substituent groups, such as an R group (e.g., R) as defined herein⁶And/or R⁷). In some embodiments, the aliphatic amine may comprise an amino group.

In some embodiments, the imidazolium cation may comprise a second amine in addition to the first amine. In some embodiments, the second amine may comprise an arylamine. In some embodiments, the arylamine may have two substituents, which may be R¹、R²、R³、R⁴And/or R⁵At least two of (1), preferably R¹And R²As a complement to the first amine on one of the other R groups. In some embodiments, the arylamine can be an imidazolium group. In some embodiments, the imidazolium group may be only at R¹、R²And R³Wherein R includes a substituent group⁴And R⁵Is hydrogen.

In some embodiments, the ionic composition can comprise a fluoroalkylsulfonimide compound having the structure of formula 4 as provided below:

the structure of formula 4 may comprise any substituted R group for each independently R⁸Such as those described herein or other known ones. Further, each n may be, for example, 0, 1,2, 3, or 4, or other integer.

In some embodiments of formula 4, each R is⁸May be hydrogen or halogen, respectively. In thatIn some embodiments of formula 4, each R is⁸May be hydrogen or fluorine, respectively. In some embodiments, at least one R is⁸Is halogen, such as fluorine. In some embodiments, for each sulfonyl, at least one R⁸Is halogen, such as fluorine. In some embodiments, there is only one R per sulfonyl group⁸Is halogen, such as fluorine.

In some cases, the ionic composition can comprise an imidazolium cation with or without a sulfonimide anion (e.g., bis (fluorosulfonyl) imide). In some cases, the ionic composition may comprise a sulfonimide anion with or without an imidazolium cation. In any configuration, the ionic composition may be used as an adhesive or coating layer, or other layer.

In some embodiments, the ionic composition can include a cation having an amino group, a linking group, and an imidazolium group, wherein the amino group and imidazolium group are bonded to each other via the linking group (e.g., Y). In some embodiments, the cation may be a composition having an anion. In some embodiments, the anion may be bis (fluorosulfonyl) imide.

In some embodiments, the ionic composition is free of 1-ethyl-3-methyl-imidazolium bis (fluorosulfonyl) imide (1-ethyl-3-methyl-imidazolium bis (fluorosulfonyl) imide).

In some embodiments, the ionic compositions described herein having an imidazolium cation and a bis (fluorosulfonyl) imide anion can be represented as follows:

in this formula, the amino group may comprise an R group as defined herein, as for R¹、R²、R⁶And/or R⁷May be hydrogen or a substituent as defined herein. This formula may also include a linking group defined as Y.

In some embodiments, the ionic compositions described herein having imidazolium cations and/or sulfonimide anions can be formulated with polymers. The polymer may be selected based on its functionality in view of the desired functionality. In some aspects, the polymer formulated in the ionic composition may comprise an acrylic polymer.

In some embodiments, the polymer (e.g., together with imidazolium cations and/or sulfonimide anions) formulated in the ionic composition can be a polymer suitable for use as an adhesive or coating that is selectively debondable, such as by applying a debonding process to the adhesive or coating. Suitable polymers may include polymers described in WO2017/064918 and/or JP2017-075289, which are incorporated herein by specific reference in their entirety. In some aspects, the polymer may comprise a glass transition temperature of less than 0 ℃. In some aspects, the polymer may be an acrylic polymer. In some aspects, the acrylic polymer may comprise a polymer derived from formula R^aCH＝CHCC₂R^bWherein R is^aIs H or C₁-C₁₄Alkyl (e.g. methyl, ethyl, C)₃Alkyl radical, C₄Alkyl radical, C₅Alkyl radical, C₆Alkyl, etc.), and R^bIs H is C_1-14Alkyl (e.g. methyl, ethyl, C)₃Alkyl radical, C₄Alkyl radical, C₅Alkyl radical, C₆Alkyl groups, etc.). In some embodiments, the polymer comprises repeat units derived from acrylic acid, methyl acrylate, methacrylic acid, methyl methacrylate, or a combination thereof. In some aspects, the acrylic polymer can comprise alkyl methacrylate and monomer units derived from a polar group-containing monomer. In some aspects, the polar group-containing monomer (e.g., polar monomer) can be a carboxyl-containing monomer. In some aspects, contains C_1-14The alkyl methacrylate of the alkyl group is butyl methacrylate, and may be methyl methacrylate, ethyl methacrylate, propyl methacrylate, methyl ethacrylate, methyl propyl acrylate, methyl butyl acrylate or other alkyl acrylates.

In some embodiments, the polymer may be crosslinked. The crosslinked polymer may comprise a polymer that is crosslinked only with the polymer in the composition. In some aspects, the crosslinked polymer can be chemically crosslinked with an imidazolium cation. In some aspects, the crosslinked polymer may be chemically crosslinked with fluorosulfonylimide. In some aspects, the crosslinked polymer can be chemically crosslinked with imidazolium cations and fluorosulfonyl imides. The crosslinking agent that can crosslink the polymer can be selected based on the desired properties to provide a crosslinked polymer. The crosslinking agent may be suitably used for the alkyl alkylacrylate. The crosslinking agent may be an epoxy crosslinking agent, such as N, N' -tetraglycidyl-m-xylylenediamine. However, it should be recognized that any suitable crosslinking agent may be used to crosslink the polymer. The crosslinking agent may be selected to maintain the selective adhesive properties and selective debonding properties described herein. The crosslinking agent may also be selected to maintain the corrosion resistance properties described herein.

Any suitable amount of ionic liquid can be used in the adhesive composition. In some embodiments, the ionic liquid or ionic compound is about 0.0-1%, about 1-2%, about 2-3%, about 3-4%, about 4-5%, about 5-6%, about 6-7%, about 7-8%, about 8-9%, about 9-10%, about 10-15%, about 15-20%, about 20-25%, about 25-30%, about 30-40%, about 40-50%, about 50-100%, about 4.5-5%, or about 5% of the total weight of the ionic liquid plus polymer.

In some embodiments, a device comprising any of the foregoing compounds is described. Suitable examples of such devices may be as described in JP2017-075289 and/or WO2017/064925, which are incorporated herein by specific reference in their entirety. Thus, the device can be an electronic device comprising a conductive substrate having the selective adhesive composition described herein. In some aspects, the device may comprise a battery.

The ionic composition may be used as a selective debonding layer on the surface of a substrate, such as an adhesive layer or a coating layer as described herein. In some aspects, the ionic composition configured as a selectively debondable layer may be placed or otherwise located between two conductive surfaces, such as between a first conductive surface and a second conductive surface. A selective debonding layer formed from an ionic composition may be applied between the first conductive surface and the second conductive surface as an adhesive layer (e.g., a selective adhesive) to adhere a first substrate having a first conductive surface to a second substrate having a second conductive surface. The adhesive layer may be considered selectively adhesive because a debonding procedure may be performed to debond the adhesive layer from the first conductive surface and/or the second conductive surface. The debonding procedure may include applying electrical energy (e.g., via an electromotive force) to the first conductive substrate and/or the second conductive substrate to debond the adhesive layer therefrom. The debonding procedure may result in reduced adhesion in the adhesive layer, and thus less adhesion to the first conductive surface and/or the second conductive surface, which allows the adhesive layer to be separated therefrom. This also allows the first conductive surface to be separated from the second conductive surface. Because the ionic composition is less corrosive and the debinding procedure allows for removal from the surface without damage, the surface can be maintained in a significantly improved state compared to existing adhesives. This improved condition may be beneficial for the reuse of substrates having such surfaces.

In some embodiments, the ionic composition is configured to have reduced or no corrosivity (e.g., not measurable or not detectable) to a metal substrate (e.g., a conductive metal substrate).

In some embodiments, the ionic composition may be provided with the ingredients described herein. In some aspects, the ionic composition has reduced lewis acidity. In some aspects, the ionic composition can comprise a suitable pH. In some aspects, the ionic composition can comprise a pH that is not excessively acidic or excessively basic. In some examples, the pH range may be from about 5 to about 9, or from about 6 to about 8 or about 7. When basic, the pH may range from about 7 to about 9, from about 7.5 to about 8.5, or about 8.

The selectively debondable layer may be used in a selectively debondable structure for adhering two non-conductive materials to each other and then releasing the adhesion so that the debonded material does not contain any conductive materials or layers. This type of structure comprises a conductive layer with a selectively debondable layer adhered to each side. Each of these adhesive layers may then be adhered to the non-conductive material, thereby providing adhesion between two non-conductive structures. An electromotive force may then be applied to the conductive layer to reduce adhesion in both adhesive layers. Thus, two non-conductive structures may be adhered to each other and then separated without the need to first adhere or attach to a conductive layer or material.

In some embodiments, the ionic composition can be provided in various ratios of imidazolium cations and sulfonimide anions. In some aspects, the imidazolium cation: the molar ratio of sulfonimide anions may be 1:10, 1:9, 1:8.1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 1:10-1:9, 1:9-1:8.1:8-1:7, 1:7-1:6, 1:6-1:5, 1:5-1:4, 1:4-1:3, 1:3-1:2, 1:2-1:1, 1:1-2:1, 2:1-3:1, 3:1-4:1, 4:1-5:1, 5:1-6:1, 6:1-7:1, 7:1-8:1, 8:1-9:1, or 9:1-10: 1. In one aspect, the ratio of imidazolium cation to sulfonimide anion can be 1:1, or substantially equal, e.g., 0.1%, 0.5%, 0.75%, 1%, 2%, or 5% different from equal.

In some embodiments, an ionic composition may be provided to reduce molecular weight. For example, the molecular weight may be less than 160 g/mol. The molecular weight may be for species formed from imidazolium cations and/or sulfonimide anions.

Fig. 1 and 2 show an apparatus 200 having a first conductive substrate 206 and a second conductive substrate 207, the first conductive substrate 206 having a first conductive surface 208 and the second conductive substrate 207 having a second conductive surface 210. Fig. 1 illustrates a first stage bonding in which a selective adhesive material 203 is placed between and in contact (e.g., bonded) with first and second conductive surfaces 208 and 210. Thus, when adhered, the first conductive surface 208 is adhered to a first side of the selective adhesive material 203 and the second conductive surface 210 is adhered to a second side of the selective adhesive material 203.

Fig. 2 illustrates a second stage debonding, where the selective adhesive material 203 is placed between the first and second conductive surfaces 208 and 210 and is not in contact with the first and second conductive surfaces 208 and 210 (e.g., debonding). Thus, when bonded, the first conductive surface 208 is debonded from the first side of the selective adhesive material 203 and the second conductive surface 210 is debonded from the second side of the selective adhesive material 203.

As shown in fig. 1 and 2, the selective adhesive material 203 is configured as a selective debonding layer disposed between the first conductive surface 208 and the second conductive surface 210.

The selective adhesive material 203 may comprise a compound of the ionic compositions described herein. As such, the selective adhesive material 203 can be a selectively debondable layer or coating disposed between the first conductive substrate 206 and the second conductive substrate 207. A first conductive substrate 206 having a conductive surface 208 and a second conductive substrate 207 having a conductive surface 210 may each be separately disposed on two non-metallic (non-conductive) substrates or layers 201 and 202, respectively.

The first and second conductive substrates 206, 207 may be in electrical communication with a power source 204 (e.g., DC, but may also be AC) to complete a closable circuit with an intermediate switch 205, or the first and second conductive substrates 206, 207 may be attached to the power source when debonding is desired. When the switch 205 is open, as shown in fig. 1, there is no electromotive force, such that the selective adhesive material 203 adheres to both the first conductive surface 208 and the second conductive surface 210, the first conductive surface 208 and the second conductive surface 210 can be a metal coating-adhesive interface. When the switch 205 is closed, as shown in fig. 2, an electromotive force is generated in which the two substrates or layers 201 and 202 can be separated from the selective adhesive material 203, thereby separating the selective adhesive material 203 from both the first conductive surface 208 and the second conductive surface 210. The DC voltage may typically be from about 3V to about 100V, but may also vary as needed or desired.

In some embodiments, the selective adhesive material 203 may also be referred to as a selective debonding layer because of its ability to selectively bond in the absence of current or selectively debond in the presence of current. Material 203 may comprise a selective binder material, which may be formed from ionic compositions described herein. In some aspects, the material 203 can bond and connect the first conductive surface 208 and the second conductive surface 210 together, wherein application of an electromotive force to the conductive material of the first conductive substrate 206 or the second conductive substrate 207 can reduce adhesion of the material 203. In some aspects, material 203 can comprise an ionic composition having at least a compound of formula 1. In some embodiments, material 203 may comprise an ionic composition having a compound of formula 1 and a compound of formula 2. In some cases, the ionic composition may comprise a compound of formula 3 in place of the compound of formula 1 or additionally comprise a compound of formula 3 in addition to the compound of formula 1. In some cases, the ionic composition may comprise a compound of formula 4 in place of a compound of formula 2 or additionally comprise a compound of formula 4 in addition to a compound of formula 2. As such, the ionic composition may comprise at least one cation of formula 1 or formula 3, and may or may not comprise an anion of at least one of formula 2 or formula 4.

Without wishing to be bound by theory, it is believed that movement of ions within the material 203 formed by the ionic composition may be achieved by applying an electrical potential thereto. When a sufficient amount of motion is achieved, such as sufficient ionic composition adjacent to the conductive surface (e.g., 208 and/or 210), the adhesive quality of the material 203 formed by the ionic composition may be reduced, thereby enabling one or both of the conductive surfaces 208, 210 to be separated from the material 203.

The selective adhesive material 203 (e.g., also a selective debonding layer) may be a selective debonding layer or coating disposed between the first conductive substrate 206 and the second conductive substrate 207, the selective adhesive material 203 comprising a compound of formula 1 and/or formula 3 and either comprising or not comprising an anion of at least one of formula 2 and/or formula 4.

The first conductive substrate 206 and the second conductive substrate 207 may be any conductive material, such as a metal. One example of a conductive metal that can be used for the first conductive substrate 206 and the second conductive substrate 207 is aluminum. The conductive material may comprise conventional materials such as metals, mixed metals, alloys, metal oxides, mixed metal oxides, conductive polymers, conductive plastics or conductive carbonaceous materials. Examples of suitable metals include group 1 metals and group 4-15 metals. Examples of suitable metals include, but are not limited to, stainless steel, Al, Ag, Mg, Ca, Cu, Mg/Ag, LiF/Al, CsF and/or CsF/Al and/or alloys thereof. In some embodiments, the conductive layers (e.g., the first conductive substrate 206 and the second conductive substrate 207) and/or the adhesive layers may each have a thickness of about 1nm to about 1000 μ ι η, or 1nm to about 100 μ ι η, or 1nm to about 10 μ ι η, or 1nm to about 1 μ ι η, or 1nm to about 0.1 μ ι η, or 10nm to about 1000 μ ι η, or 100nm to about 1000 μ ι η, or 1 μ ι η to about 1000 μ ι η, or 10 μ ι η to about 1000 μ ι η, or 100 μ ι η to about 1000 μ ι η. In some aspects, the thickness may be 20nm to about 200 μm, or 100nm to about 100 μm, or 200nm to about 500 μm.

The two non-conductive substrates or layers 201 and 202 may be any non-conductive material. Some examples may include non-conductive wood, cardboard, fiberglass density fiberboard or plastic, as well as any other non-conductive material. In some aspects, layers 201 and 202 may be electrical insulators. In some aspects, layers 201 and 202 may be semiconductors. Any non-conductive substrate 201 or 202 or semiconductor substrate (e.g., printed circuit board, PCB) can have any thickness and can be coupled to other substrates, materials, or devices.

In some embodiments, the ionic composition of the selective adhesive material 203, whether configured as an adhesive or a coating, can have a reduced corrosive effect on the conductive layer of the first conductive substrate 206 or the second conductive substrate 207. The reduced corrosion effect may be compared to the corrosion effect of other ionic compositions. A suitable protocol for evaluating the corrosive effect of material 203 on electrically conductive materials may include the procedure described in ASTM G69-12 (Standard Test Method for Measurement of Corrosion potential of aluminum alloys ), which is incorporated herein by specific reference in its entirety. Suitable additional approaches to evaluating the corrosive effect of the ionic composition material 203 on the conductive material of the first conductive substrate 206 or the second conductive substrate 207 may be achieved by: the interface between the material 203 (e.g., adhesive) and the conductive substrate (e.g., aluminum foil) is visually inspected to determine if there is any indication of corrosive degradation of the substrate and/or dissolution of the material from the conductive substrate (e.g., metal) into the material 203 and/or pitting (staking) of the surface of the conductive substrate. If corrosion was observed, the time was recorded and the sample was shown to be corrosive as shown in Table 1 below.

In some embodiments, the selective binder material may be chemically stable with the conductive electrode or conductive material. That is, the selective adhesive material avoids chemical degradation when applied to a conductive electrode or conductive material, whether in the adhesion phase in the absence of electrical current or in the debonding phase in the presence of electrical current. As such, the selective adhesive material may be considered to be chemically stable during use. The stability of the selective binder material can be maintained when disposed on aluminum, stainless steel, and/or combinations and/or mixtures thereof. In some aspects, the chemical stability of the selective binder material is defined as the absence (or minimal presence) of an undesirable reaction between the conductive material and the selective binder material. The undesirable reactions may include, for example, corrosive degradation of the conductive material, dissolution of the conductive material into the selective binder material, and/or pitting of the conductive material.

In some embodiments, the ionic compositions described herein formed as selective binder materials may result in reduced or absent corrosive degradation thereof when deposited on or in contact with a conductive material. In some embodiments, direct contact of a pure ionic compound (e.g., imidazolium cation and/or sulfonimide anion) or an ionic composition or selective adhesive material formed from an ionic composition on a conductive material may exhibit an absence or minimization of any corrosive degradation thereof for at least or greater than 15 minutes, 30 minutes, 1 hour, 3 hours, 5 hours, 7 hours, 24 hours, 50 hours, 100 hours, 125 hours, 200 hours, and/or 300 hours. In some aspects, direct contact of the pure ionic compound or ionic composition or selective binder material on the conductive material can minimize and/or prevent corrosive degradation thereof for a period of time as described above. In some aspects, direct contact of the purely ionic compound or ionic composition or selective binder material on the conductive material can minimize and/or prevent corrosive degradation thereof for a period of time as described above in a 60 ℃/90% Relative Humidity (RH), 85 ℃/85% RH, or 90 ℃/80% RH environment, or any humidity and/or temperature range therebetween. In some aspects, one suitable approach to illustrating the absence of any corrosive degradation may be by verifying that there is not complete penetration into the surface of the conductive material. In one example, the conductive material may be an approximately 50nm thick conductive sheet of aluminum foil, and may be tested for corrosivity during the above-described time periods and/or ambient conditions.

In some embodiments, the selective adhesive materials formed from the ionic compositions described herein can be formulated to minimize corrosion of the conductive substrates described above under long-term high humidity and high temperature conditions. In particular, the adhesive composition is capable of maintaining two such conductive substrates in a fixed relationship to each other during and after being subjected to aging. This corrosion resistance has been demonstrated by accelerated aging test method II described herein, which may include exposure to 90 ℃/80% RH for a period of time as described herein. As is known from the guidance provided herein, selective adhesive materials can be made using techniques known in the art.

Examples

It has been found that embodiments of the ionic compositions and selective binder materials described herein can reduce degradation and/or corrosion of the conductive materials (e.g., conductive metal layers) described herein. These benefits are further illustrated by the following examples, which are intended to be illustrative of embodiments of the present disclosure, but are not intended to limit the scope or underlying principles in any way.

Synthesis of ionic compositions