Ionic compositions and uses related thereto
阅读说明：本技术 离子组合物及其相关用途 (Ionic compositions and uses related thereto ) 是由 史丹尼斯劳·瑞瓦尔 胡毓芬 张洪喜 于 2018-03-02 设计创作，主要内容包括：本公开总体上涉及离子组合物,其可用在粘合材料中或作为粘合材料用于选择性地将两个物品粘合在一起。更具体地但非排他性地,本公开涉及包含阳离子咪唑鎓化合物和阴离子化合物例如磺酰亚胺化合物的离子组合物。(The present disclosure relates generally to ionic compositions that can be used in or as an adhesive material for selectively bonding two items together. More particularly, but not exclusively, the present disclosure relates to ionic compositions comprising a cationic imidazolium compound and an anionic compound, such as a sulfonimide compound.)
1. A composition comprising a cationic compound according to formula (I):
wherein R is1Represents C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8Alkoxyalkyl radical, R2Represents hydrogen or C1-C3Alkyl radical, R3Represents C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15Arylalkyl radical, R4Represents hydrogen or C1-4Alkyl, and R5Represents hydrogen or C1-4An alkyl group.
2. The composition of claim 1, further comprising an anionic compound having the structure:
3. the composition of any of the preceding claims, wherein R4And R5At least one of which is C1-4An alkyl group.
4. The composition of any of the preceding claims, further comprising an acrylic polymer.
5. The composition of any of the preceding claims, wherein R4Represents hydrogen and R5Represents C1-4An alkyl group.
6. The composition of any one of claims 1-4, wherein R4Represents C1-4Alkyl and R5Represents hydrogen.
7. The composition of claim 1 or claim 2, wherein R1represents-CH3、-CH2-CH3or-CH2-(CH3)2。
8. The composition of any one of claims 1, 2, or 7, wherein R2represents-H, -CH3or-CH2-CH3。
9. The composition of any one of claims 1, 2, 7, or 8, wherein R3represents-CH3or-CH2-CH3。
10. The composition of any one of claims 1, 2, 7, 8, or 9, wherein R4represents-CH3And R is5Represents hydrogen.
11. The composition of any one of claims 1, 2, 7, 8, or 9, wherein R4Represents hydrogen and R5represents-CH3。
12. A device comprising a first substrate, a second substrate, and the composition of any one of the preceding claims positioned between the first substrate and the second substrate, wherein the first substrate and the second substrate are bonded together by the composite.
13. The device of claim 12, wherein the first substrate comprises a conductive surface, the second base comprises a conductive surface, and the composition is positioned in contact with the conductive surface.
14. A method comprising bonding a first substrate to a second substrate using the composition of any one of claims 1-11.
15. The method of claim 14, further comprising: applying an electrical potential between the first substrate and the second substrate, and separating the first substrate from the second substrate.
16. The method of claim 14, further comprising placing the composition on a conductive surface of the first substrate.
Background
The present disclosure relates to ionic compositions that can be used in or as an adhesive material for selectively bonding two items together. More particularly, but not exclusively, the present disclosure relates to ionic compositions comprising a cationic imidazolium compound and an anionic compound, such as a sulfonimide compound.
Certain compositions are known to be useful as adhesive coatings applied to the conductive surface of a first substrate. An adhesive coating may be sandwiched between the conductive surface of the first substrate and the conductive surface of the second substrate to bond or join the first and second substrates together. Upon application of an electrical potential, the adhesive coating debonds from one or both of the first and second substrates to separate the first and second substrates from each other. However, it has been observed that certain forms of this type of coating may have an undesirable corrosive effect on the conductive surface to which it is applied. Therefore, there remains a need for further contributions in this area of technology.
The subject matter disclosed and claimed herein is not limited to implementations that solve any disadvantages or that operate only in environments such as those described above. Rather, this context is merely provided to illustrate examples that the present disclosure may use.
Disclosure of Invention
The present disclosure relates generally to ionic compositions that can be used in or as an adhesive material for selectively bonding two items together. More particularly, but not exclusively, the present disclosure relates to ionic compositions comprising a cationic imidazolium compound and an anionic compound, such as an anionic sulfonimide compound.
In one embodiment, the composition comprises a cationic compound according to formula (I):
wherein R is1Represents C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl or C1-C8Alkoxyalkyl radical, R2Represents hydrogen or C1-C3Alkyl radical, R3Represents C1-C8Alkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15Arylalkyl radical, R4Represents hydrogen or C1-4Alkyl, and R5Represents hydrogen or C1-4An alkyl group. In one form of this embodiment, the composition further comprises an anionic compound having the structure:
in another embodiment, a device includes a first substrate and a second substrate bonded together by a composition comprising a cationic compound according to formula (I):
wherein R is1Represents C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8Alkoxyalkyl radical, R2Represents hydrogen or C1-C3Alkyl radical, R3Represents C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15Arylalkyl radical, R4Represents hydrogen or C1-4Alkyl, and R5Represents hydrogen or C1-4An alkyl group.
In another embodiment, a method comprises bonding a first substrate to a second substrate with a composition comprising a cationic compound according to formula (I):
wherein R is1Represents C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8Alkoxyalkyl radical, R2Represents hydrogen or C1-C3Alkyl radical, R3Represents C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15Arylalkyl radical, R4Represents hydrogen or C1-4Alkyl, and R5Represents hydrogen or C1-4An alkyl group.
This summary introduces a number of concepts in a simplified form that are further described below in the detailed description. This summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used as an aid in determining the scope of the claimed subject matter.
Additional features and advantages will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice. The features and advantages may be realized and obtained by means of the instruments and combinations particularly pointed out in the appended claims. These and other features will become more fully apparent from the following description and appended claims.
Drawings
Fig. 1 is a schematic representation of the use of an ionic composition described herein for bonding two substrates together.
Fig. 2 is a schematic illustration of the peeling or debonding of the two substrates of fig. 1 upon application of an electrical potential.
Fig. 3 is a schematic illustration of an apparatus for testing the adhesive properties of the ionic compositions described herein.
Figure 4 is a graph of peel strength density of ionic compositions described herein versus time tested in the apparatus shown in figure 3.
Detailed Description
For the purposes of promoting an understanding of the disclosure, reference will now be made to the following embodiments and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of the disclosure is thereby intended, such alterations and further modifications in the described subject matter, and such further applications of the principles disclosed as described herein being contemplated as would normally occur to one skilled in the art to which the disclosure relates.
The present disclosure relates generally to ionic compositions that can be used in or as an adhesive material for selectively bonding two items together. More particularly, but not exclusively, the present disclosure relates to ionic compositions comprising a cationic imidazolium compound and an anionic compound, such as a sulfonimide compound.
As used herein, when a compound or chemical structure is referred to as "optionally substituted," the compound or chemical structure includes features that have no substituents (i.e., are unsubstituted), or features that are "substituted" (meaning that the feature has one or more substituents). A substituted group is derived from an unsubstituted parent structure, wherein one or more hydrogen atoms on the parent structure have been independently substituted with one or more substituents. The substituted group may have one or more substituents on the parent group structure. In one or more forms, the substituents may be independently selected from optionally substituted alkyl or alkenyl, alkoxy (e.g., -OCH)3、-OC2H5、-OC3H7、-OC4H9Etc.), alkylthio (alkylthio) groups (e.g., -SCH3、-SC2H5、-SC3H7、-SC4H9Etc.), -N 'R' R ", -OH, -SH, -CN, -NO2Or halogen, wherein R 'and R' are independently H or optionally substituted alkyl.
As used herein, the term "imidazolium" refers to a ring system having the structure:
as used herein, the terms "bis (sulfonyl) imide (bis) imide) and/or sulfonimide (sulfonyl imide)" refer to, for example, a heteroatom fragment having the structure:
in one embodiment, the ionic composition comprises a cationic imidazolium compound according to formula (I):
wherein R is1Can represent C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8An alkoxyalkyl group; r2May represent hydrogen or C1-C3An alkyl group; r3Can represent C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15An arylalkyl group; and R is4And R5May independently represent hydrogen or C1-4An alkyl group.
In some forms, R1、R2、R3、R4And R5One or more of which may represent a hydrophilic functional group. In a more particular form, R1、R2And R3One of which may represent a hydrophilic functional group. In one or more of these forms, the hydrophilic functional group can comprise oxygen. In some forms, the oxygen-containing hydrophilic functional group may include an ether, hydroxyl, alkoxy, and/or ester group. In other forms, the hydrophilic functional group may comprise nitrogen, sulfur, and/or phosphorus. In other forms, the hydrophilic functional group may include an amino group, a sulfhydryl group, or a phosphate group.
In one or more forms, R1、R2、R3、R4And R5One or more of which may represent a hydrophobic functional group. In a more particular form, R1、R2And R3One or more of which may represent a hydrophobic functional group. In one or more of these forms, the hydrophobic functional group can include an optionally substituted alkyl group. In some forms, the optionally substituted alkyl may include methyl, ethyl, and/or propyl. In other forms, the hydrophobic functional group can include an optionally substituted aryl group. In certain forms, the optionally substituted aryl group can include phenyl and/or benzyl.
In one or more forms, R1、R2、R3、R4And R5May be independently substituted and the cationic compound according to formula (I) may be asymmetric.
As mentioned above, R1Can represent C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8An alkoxyalkyl group. In some more specific forms, R1Can represent C1-C3Alkyl or C1-C3An alkoxyalkyl group. In one or more of these forms, C1-C3The alkyl group may be methyl, ethyl, n-propyl or isopropyl. In some forms, C1-C8Alkoxyalkyl may represent methoxymethyl.
As mentioned above, R2May represent hydrogen or C1-C3An alkyl group. In some more specific forms, R2May represent hydrogen. In some more specific forms, R2May represent a methyl or ethyl group.
As mentioned above, R3Can represent C1-C8Alkyl radical, C1-C8Hydroxyalkyl radical, C1-C8Alkenyl radical, C1-C8Alkoxyalkyl, Acetyloxy C1-C3Alkyl or C7-C15An arylalkyl group. In some more specific forms, R3Can represent C1-C8Alkyl radical, C1-C8Alkenyl or C1-C8An alkoxyalkyl group. In some other forms, R3Can represent C1-C3Alkyl radical, C1-C3Alkoxy radical, C1-C3Hydroxyalkyl radicals (e.g. -CH)2CH2-OH)、C1-C3Alkoxy, acetoxy C1-C3Alkyl or C5-C7Arylalkyl (e.g., -CH)2-phenyl). In some forms, R3May represent a methyl or ethyl group. In other forms, R3Can represent C1-C3Alkoxy, which may be, for example, methoxy or ethoxy. In some forms, R3Can represent C1-C3Hydroxyalkyl radicals, e.g. -CH2CH2-OH. In some forms, R3May represent a methoxymethyl group or an ethoxymethyl group. In other forms, R3Can represent acetoxy C1-C3An alkyl group, which may be an acetoxyethyl group. In some forms, R3Can represent C5-C7Arylalkyl, which may be benzyl.
As mentioned above, R4And R5May independently represent hydrogen or C1-4An alkyl group. In a more particular form, R4And R5Is at least one of C1-4An alkyl group. In a particular form, R4Represents C1-C2Alkyl radical, R5Represents hydrogen. In another form, R4Represents hydrogen and R5Represents C1-C2An alkyl group. In another form, R4Represents methyl, and R5Represents hydrogen. In another form, R4Represents hydrogen, and R5Represents a methyl group. In another form, R4And R5One or two of them represent C1-C2An alkyl group. In another form, R4And R5One or two of them represent C1-C4An alkyl group. In another form, R4Represents C1-C2Alkyl or C1-C4Alkyl, and R5Represents hydrogen. In another form, R5Represents C1-C2Alkyl or C1-C4Alkyl, and R4Represents hydrogen. In another form, R4And R5All represent C1-C2Alkyl, which may be, for example, methyl and/or ethyl. In another form, R4And R5All represent CH3。
In addition, other variants of the cationic compounds according to formula (I) are also possible. For example, in one form, R1Can be selected from-H, -CH3、-CH2-CH3、-CH2-(CH3)2and-CH2-O-CH3，R2Can be selected from-H, -CH3and-CH2-CH3，R3Can be selected from-H, -CH3、-CH2-CH3、-CH2-(CH3)2、-CH2-O-CH3、-CH2-CH2-OH、-CH2-CH2-O-CH3、R4Can be selected from-H, -CH3or-CH2-CH3And/or R5Can be selected from-H, -CH3and/or-CH2-CH3. As another example, in another mode, R1May be selected from-CH3、-CH2-CH3、-CH2-(CH3)2and-CH2-O-CH3，R2Can be selected from-H, -CH3and-CH2-CH3，R3May be selected from-CH3、-CH2-CH3、-CH2-O-CH3、-CH2-CH2-O-CH3OrR4May be selected from-H or-CH3And/or R5May be selected from-H or-CH3. In yet another example, in another form, R1May be selected from-CH3、-CH2-CH3and-CH2-(CH3)2，R2Can be selected from-H, -CH3and-CH2-CH3，R3May be selected from-CH3and-CH2-CH3，R4May be selected from-H or-CH3And/or R5May be selected from-H or-CH3。
Representative compounds according to formula (I) include, but are not limited to, those shown in table 1:
TABLE 1
The ionic compositions disclosed herein may also comprise anionic compounds. In one form, the anionic compound may be a bis (sulfonyl) imide anion. In a more particular form, the bis (sulfonyl) imide anion can be a bis (fluorosulfonyl) imide compound. In one form, the bis (fluorosulfonyl) imide compound can have the following structure:
the ionic compositions described herein may be used as or in an adhesive material that may be used to releasably bond two or more articles together. In other words, the adhesive material can be used to selectively bond the articles together, thereby allowing the adhesive material to debond from one or more articles and, if desired, facilitate separation of the articles. More particularly, an adhesive material according to the present disclosure may be disposed on the conductive surface of the first substrate, and the conductive surface of the second substrate may be positioned in contact with the adhesive material so as to adhere or join the first and second substrates together. In this configuration, the adhesive material is sandwiched between the first substrate and the second substrate, but other variations are conceivable. As described above, the adhesive material facilitates debonding and separation of the first and second substrates, if desired. More specifically, upon application of an electrical potential, the adhesive material will debond or peel away from the conductive surface of one or both substrates, thereby causing the first and second substrates to separate from each other.
Although not previously described, it is to be understood that the compositions disclosed herein may comprise components other than cationic and anionic compounds. For example, in one form, the composition may further comprise a polymer. Non-limiting examples of polymers that may be present in the composition include those described in JP 2015-204998 and/or JP 2015-204996. In one form, the polymer may have a glass transition temperature below 0 ℃, although other variations are possible. In one form, the polymer may be an acrylic polymer, such as but not limited to, a polymer comprising a polymer derived from a C-containing polymer1-C14Acrylic polymers of monomeric units of alkyl (meth) acrylates of alkyl groups. However, in other forms, the acrylic polymer may comprise a polymer derived from C1-C14Alkyl or alkoxy groups. In one form, the acrylic polymer may comprise alkyl (meth) acrylates and monomer units derived from polar group-containing monomers. In one aspect of this form, the polar group-containing monomer can be a carboxyl-containing monomer. In another or alternative aspect of this form, C is1-C14The alkyl (meth) acrylate of the alkyl group is butyl (meth) acrylate.
It is contemplated that the compositions described herein may be used in many different applications, including for example those disclosed in JP 2015-.
Referring now to fig. 1 and 2, additional details will be provided regarding the use of ionic compositions described herein in an apparatus 200 for selectively bonding two substrates together. The bonding material 203, which includes the ionic composition described herein, provides a layer or coating between the conductive surface 206 of the substrate 202 and the conductive surface 207 of the substrate 201. In one form, one or both of the substrates 201, 202 may be formed of an electrically conductive material such that one or both of the conductive surfaces 206, 207 is formed of the same material as the remainder of the substrates 201, 202. However, in other forms, one or more conductive materials different from the material forming the substrates 201, 202 may be used for the conductive surfaces 206, 207. Similarly, it should be understood that one or both of the bases 201, 202 may be formed of one or more materials that are not electrically conductive, so long as the surfaces 206, 207 are electrically conductive. In these forms, the conductive surfaces 206, 207 may be disposed as a coating or layer on the substrates 201, 202.
In the form shown, the conductive surfaces 206, 207 are electrically coupled to the power source 204 or in electrical communication with the power source 204 in a closable circuit that includes an intermediate switch 205. In one form, the power supply 204 may be a direct current power supply that may provide a DC voltage in the range of about 3V to 100V, although other variations are contemplated. When the switch 205 is closed, an electrical potential is applied between the conductive surfaces 206, 207 to debond the adhesive material 203 from one or both of the conductive surfaces 206, 207 and, as a result, allow the substrates 201 and 202 to be physically separated from each other.
In one form one or both of the substrates 201, 202 may comprise a conductive carbonaceous material or a conductive metal. As described above, one or both of the substrates 201, 202 may also include a conductive layer, which may be formed of a metallic material such as, but not limited to, aluminum. The conductive layer may comprise conventional materials, such as metals, mixed metals, alloys, metal oxides and/or complex metal oxides, or it may comprise a conductive polymer. Examples of suitable metals for the conductive layer include group 1 metals, metals from groups 4, 5, 6, and group 8-10 transition metals. Other examples of suitable metals for the conductive layer include stainless steel, Al, Ag, Mg, Ca, Cu, Mg/Ag, LiF/Al, CsF and/or CsF/Al and/or alloys thereof. The conductive layer, if present, may have a thickness in the range of about 1nm to about 1000 μm. In one form the conductive layer has a thickness of about 20nm to about 200 μm, and in another form the conductive layer has a thickness of about 20nm to about 200 nm.
Although not previously discussed, it is to be understood that the ionic compositions described herein may provide various properties desirable for certain applications. For example, in certain forms, the ionic compositions disclosed herein can eliminate or reduce corrosion of the conductive surface on which they are located. For example, in one form, the ionic compositions disclosed herein include a component that reduces the acidity of the environment proximate the conductive surface. In one aspect, the binding material may comprise one or more materials, in addition to the cationic and anionic compounds themselves, which may be used to reduce the corrosivity of ionic cations and/or anions in close proximity to the conductive surface. The corrosion effect of the adhesive material can be evaluated according to the procedure described in ASTM G69-12 (Standard test method for measuring the Corrosion potential of aluminum alloys). Additional procedures for evaluating the corrosive effects of adhesive materials on conductive surfaces are described in the examples of the present application.
In one form, the binding material comprising the ionic compositions disclosed herein may be chemically stable with respect to the conductive electrode or on the conductive material, i.e., there is no (or minimal) undesired reaction between the metal electrode and the binding material. Undesirable reactions may include, for example, corrosion degradation of the metal electrode, dissolution of the metal in the selectively adhered binder, and/or pitting of the metal electrode. To provide just a few examples, the bonding materials comprising the ionic compositions disclosed herein can be chemically stable with respect to aluminum, stainless steel, and/or mixtures thereof. In one form, contact of the adhesive material comprising the ionic compositions disclosed herein on the conductive surface can result in a reduction or absence of any corrosive degradation of the surface over a period of at least (or greater than) about 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 forms, direct contact of an adhesive material comprising the ionic compositions disclosed herein on an electrically conductive surface at an elevated temperature of 85 ℃ and a high relative humidity of 85% can minimize and/or prevent corrosive degradation of the surface for a period of time as described above. In one form, no corrosion degradation is observed because of the lack of total penetration of a 50nm thick conductive aluminum foil over the time frame and/or ambient conditions described above.
In one form, the adhesive material comprising the ionic composition described herein can be formulated to minimize corrosion of conductive surfaces under high humidity and high temperature conditions for extended periods of time. For example, the adhesive composition may be capable of holding two substrates in a fixed relationship to each other during and after performing accelerated aging test method II (preferably after exposure to 85 ℃ and 85% relative humidity for a period of time specified above). Also, while not previously discussed, it is to be understood that the ionic compositions disclosed herein can have a molar mass of less than or equal to about 160 grams/mole.