CURABLE SILICONE-BASED COMPOSITIONS AND USE THEREOF

Abstract

A curable composition comprising: a polymer A, a polymer B, and one or more fillers, wherein polymer A comprises an organic molecule or a siloxane molecule containing two or more epoxy functional groups, and polymer B comprises an organic amine or a hybrid silicone amine.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to and the benefit of Indian Provisional Application No. 201821049326, filed on December 26, 2018, the entire disclosure of which is incorporated herein by reference in its entirety.

[0002] The present technology relates to a curable silicone-based composition. In particular, the present technology relates to a curable silicone-based composition comprising an epoxy-functionalized polymer, an amine-functionalized polymer, and a filler, the composition providing a silicone composite upon curing. [Background technology]

[0003] Silicones are known for their inherent properties such as high thermal stability, flexibility, and / or chemical resistance. Siloxanes are used in electronic or electrical applications based on such properties. It can be desirable to use siloxanes in applications where electrical conductivity may be important, but developing conductive siloxane materials is difficult.

[0004] Electrical properties can be achieved in silicones by adding fillers to the silicone matrix, and the desired electrical conductivity can be achieved by increasing the loading of fillers in the composition. However, at higher loadings, the filler particles may separate from the composition over a period of time. Thus, dispersion of highly loaded fillers into the siloxane matrix is ​​a major challenge. Higher loadings of fillers in the composition can also adversely affect the cure kinetics and processability of the composition. Other common challenges include, but are not limited to, variable contact resistance and volume resistivity.

[0005] To solve these technical problems, efforts have been made to develop curable silicone compositions with desirable mechanical and chemical properties. Summary of the Invention

[0006] Provided is a curable silicone composition that can provide good electrical conductivity as well as desirable adhesion and other mechanical and chemical properties.In some embodiments, the present technology provides a curable composition that includes polymer A, polymer B, and one or more fillers, where polymer A includes organic molecules or siloxane molecules that include two or more epoxy functional groups, and polymer B includes organic amines or hybrid silicone amines.

[0007] In some embodiments, the curable composition comprises polymer A, polymer B, and one or more fillers. The curable silicone composition is an epoxyamine cure system: where the cured form of the curable composition is a conductive material. Polymer A can be represented by Formula 1: (R) a (W) b (R) a’’ formula 1 where b is greater than 0, a is equal to a'', and (a+a'') is greater than 1. R can be expressed by the formula (1a): (L1) c [(CH2) d (CH2O) e X] f Formula (1a) wherein L1 is a heteroatom independently selected from oxygen or nitrogen, and wherein c, e can be 0 or greater, and d, f are greater than 0, with the proviso that (d+e) is greater than 0. Further in formula (1a), X can be independently selected from any of the functional moieties represented by formula (1b): [ka] where g, h, i can be 0 or greater, and j, k can be 0 or greater, with the proviso that (j+k) is greater than 0. R1 is an aliphatic or aromatic substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C1-C 20 It is selected from those having carbon atoms and optionally bonded to an ester. W in formula 1 can be expressed by formula (1c): (Y) l (Z) m Formula (1c) Here, l and m can be zero or greater, provided that l+m>0. Furthermore, Y in formula (1c) can be expressed by formula (1d): (M1) n’’ (D1) n (D2) o (T1) p (Q1) q (M2) n’’’ Formula (1d) where n, o, p, q, n'', and n'' can be zero or greater, provided that n+o+p+q+n''+n''>0. Furthermore, M1 in formula (1d) is represented by formula (1e), R2R3R4SiO 1 / 2 Formula (1e) Here, D1 is expressed by formula (1f), R5R6SiO 2 / 2 Formula (1f) Here, D2 is expressed by formula (1g). R7R8SiO 2 / 2 Formula (1g) Here, T1 is expressed by formula (1h), R9SiO 3 / 2 Formula (1h) Here, Q1 is expressed by the formula (1i), SiO 4 / 2 Formula (1i) Here, M2 is expressed by equation (1j), R 10 R 11 R 12 SiO 1 / 2 Formula (1j) Here, R2-R 12 can be selected independently of R with c=0, or R2-R 12 is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having a C1-C 20 The alkyl groups may be independently selected from those having carbon atoms. Z in formula (1c) can be expressed by formula (1k), (A') r (B') s Formula (1k) where r and s may be zero or greater, with the proviso that r+s is always greater than zero; wherein A' can be selected from bisepoxides having a structure represented by formula (1l): R 13 (J) s’’ R 14 Formula (1l) Here, J is R 15 , R 16 and s''≧0. Furthermore, R 13 -R 16 is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having a C1-C 20 B' in formula (1k) can be selected from the structures represented by formula (1m): (CH2) t [(CHOH) u (OCHR 17 (CH2) v O w [(CH2) x L2] y R 18 R 19 R 20 CR 21 ]z formula (1m) Here, R 17 -R 21 is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having a C1-C 20 L2 is a heteroatom independently selected from oxygen or nitrogen, where t, u, v, w, x, y, and z are integers, with the proviso that t+u+v+w+x+y+z>0.

[0008] In some embodiments, polymer B can be represented by formula 2: (R') a’ (W') b’ (R') a’ Formula (2) Here, a' and b' can be 0, provided that (a'+b') is greater than 0. R' can be represented by formula (2a): (CH2) c’ (OCH2CHR 22 ) d’ (R 23 L3R 24 ) e’ Formula (2a) c', e' are greater than 0, and d' may be zero or greater, provided that c'+d'+e'>0; L3 is nitrogen, and L3 is nitrogen, and L3, R 23 , R 24 can be 0, provided that e' is 0. R 22 is hydrogen, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C1-C 20 may be independently selected from those having carbon atoms, R 23 , R 24 can independently be 0, where (R 23 +R 24 ) is greater than 0, W' can be expressed by the formula (2b): (Y') f (Z') g’ Formula (2b) f' and g' are 0 or greater, and (f'+g') is greater than 0, where Y' can be represented by Equation 2c: (M3) r’ (D3) h’ (D4) i’ (T2) j’ (Q2) k’ (M4) s’ Equation 2(c) h', i', r', s', j', and k' may be zero or greater, provided that (h'+i'+r'+s'+j'+k')>0; M3 is expressed by formula (2d), R 25 R 26 R 27 SiO 1 / 2 Formula (2d) D3 is expressed by formula (2e), R 28 R 29 S 2 / 2 Formula (2e) D4 is represented by formula (2f). R 30 R 31 SiO 2 / 2 Formula (2f) T2 is represented by formula (2g), R 32 SiO 3 / 2 Formula (2g) Q2 is expressed by formula (2h), SiO 4 / 2 Formula (2h) M4 is expressed by formula (2i), R 33 R 34 R 35 SiO 1 / 2 Formula (2i) R 25 -R 35 is selected from R' or from hydrogen, a hydroxyl radical, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C1-C 20 The alkyl groups may be independently selected from those having carbon atoms. Z' in formula (2b) can be expressed by formula (2j), R 36 L4(CH l’ ) m’ R 37 L5(CH n’ ) o’ L6R 38 (CH p’ ) q’ Formula (2j) Z' in formula (2j) can be linear or cyclic. In formula (2j), R 36 -R 38may be independently selected from hydrogen, or monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having halogen optionally bonded through 1-20 carbon or heteroatoms. L4, L5, or L6 are heteroatoms independently selected from oxygen or nitrogen; L4, L5, or L6 may be 0 or greater, provided that (L4+L5+L6) is greater than 0; and l', m', n', o', p', and q' are integers, provided that l'+m'+n'+o'+p'+q'>0.

[0009] These and other embodiments and aspects are further understood with reference to the following detailed description. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] In the following specification and in the claims that follow, reference will be made to a number of terms that shall be defined to have the following meanings.

[0011] The singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. "Optional" or "optionally" means that the subsequently described event or circumstance may or may not occur, and that the description includes instances in which the event occurs and instances in which the event does not occur.

[0012] Approximation language used throughout the specification and claims herein may be applied to modify any quantitative expression that may be permissibly varied without resulting in a change in the basic function to which it relates. Thus, a value modified by one or more terms such as "about" is not intended to be limited to the exact value specified. In some instances, the approximation language may correspond to the precision of an instrument for measuring the value.

[0013] As used herein, the terms "aromatic", "aromatic group", and "aromatic radical" are used interchangeably and refer to an array of atoms having at least one valence that includes at least one aromatic group. The array of atoms having at least one valence that includes at least one aromatic group may include heteroatoms such as nitrogen, sulfur, selenium, silicon and oxygen, or may be composed exclusively of carbon and hydrogen. As used herein, the term "aromatic radical" includes, but is not limited to, phenyl, pyridyl, furanyl, thienyl, naphthyl, phenylene, and biphenyl radicals. As previously mentioned, aromatic radicals include at least one aromatic group. Aromatic groups are always cyclic structures with 4n+2 "delocalized" electrons, where "n" is an integer of 1 or greater, as represented by phenyl groups (n=1), thienyl groups (n=1), furanyl groups (n=1), naphthyl groups (n=2), azulenyl groups (n=2), anthracenayl groups (n=3), and the like. Aromatic radicals may also include non-aromatic components. For example, a benzyl group is an aromatic radical that contains a phenyl ring (the aromatic group) and a methylene group (the non-aromatic component). Similarly, a tetrahydronaphthyl radical is an aromatic radical that contains an aromatic group (CH) fused to a non-aromatic component -(CH). For convenience, the term "aromatic radical" is defined herein to encompass a wide range of functional groups, such as alkyl groups, alkenyl groups, alkynyl groups, haloalkyl groups, haloaromatic groups, conjugated dienyl groups, alcohol groups, ether groups, aldehyde groups, ketone groups, carboxylic acid groups, acyl groups (e.g., carboxylic acid derivatives such as esters and amides), amine groups, and nitro groups. For example, a 4-methylphenyl radical is a C aromatic radical that contains a methyl group, where the methyl group is the functional group that is an alkyl group. Similarly, a 2-nitrophenyl radical is a C aromatic radical that contains a nitro group, where the nitro group is the functional group.Aromatic radicals include halogenated aromatic radicals such as 4-trifluoromethylphenyl, hexafluoroisopropylidenebis(4-phen-1-yloxy) (i.e., -OPhC(CF3)2PhO-), 4-chloromethylphen-1-yl, 3-trifluorovinyl-2-thienyl, 3-trichloromethylphen-1-yl (i.e., 3-CCl3Ph-), 4-(3-bromoprop-1-yl)phen-1-yl (i.e., 4-BrCH2CH2CH2Ph-). Further examples of aromatic radicals include 4-allyloxyphen-1-oxy, 4-aminophen-1-yl (i.e., 4-H2NPh-), 3-aminocarbonylphen-1-yl (i.e., NH2COPh-), 4-benzoylphen-1-yl, dicyanomethylidenebis(4-phen-1-yloxy) (i.e., -OPhC(CN)2PhO-), 3-methylphen-1-yl, methylenebis(4-phen-1-yloxy) (i.e., -OPhCH2PhO-), 2-ethylphen-1-yl, phenylethenyl, 3-formyl-2-thienyl, 2-hexyl-5-furanyl, hexamethylene-1,6-bis(4-phen-1-yl). oxy) (i.e., -OPh(CH2)6PhO-), 4-hydroxymethylphen-1-yl (i.e., 4-HOCH2Ph-), 4-mercaptomethylphen-1-yl (i.e., 4-HSCH2Ph-), 4-methylthiophen-1-yl (i.e., 4-CH3SPh-), 3-methoxyphen-1-yl, 2-methoxycarbonylphen-1-yloxy (e.g., methylsalicyl), 2-nitromethylphen-1-yl (i.e., 2-NO2CH2Ph), 3-trimethylsilylphen-1-yl, 4-t-butyldimethylsilylphen-1-yl, 4-vinylphen-1-yl, vinylidenebis(phenyl), and the like. The term "C3-C10 aromatic radical" includes aromatic radicals containing at least 3 but not more than 10 carbon atoms. The aromatic radical 1-imidazolyl (C3H2N2-) represents a C3 aromatic radical. The benzyl radical (C7H7-) represents a C7 aromatic radical. In one or more embodiments, the aromatic group can include a C6-C30 aromatic group, a C10-C30 aromatic group, a C15-C30 aromatic group, a C20-C30 aromatic group.In some particular embodiments, the aromatic group can include a C3-C10 aromatic group, a C5-C10 aromatic group, or a C8-C10 aromatic group.

[0014] As used herein, the terms "alicyclic," "alicyclic group," and "alicyclic radical" are used interchangeably and refer to a radical that has at least one valence and contains an array of atoms that is cyclic but not aromatic. As defined herein, an "alicyclic radical" does not contain aromatic groups. An "alicyclic radical" may contain one or more non-cyclic components. For example, a cyclohexylmethyl group (CH 11 CH2-) is an alicyclic radical that contains a cyclohexyl ring (a cyclic but non-aromatic arrangement of atoms) and a methylene group (the non-cyclic component). An alicyclic radical may contain heteroatoms such as nitrogen, sulfur, selenium, silicon, and oxygen, or may be composed exclusively of carbon and hydrogen. For convenience, the term "alicyclic radical" is defined herein to encompass a wide range of functional groups, such as alkyl groups, alkenyl groups, alkynyl groups, haloalkyl groups, conjugated dienyl groups, alcohol groups, ether groups, aldehyde groups, ketone groups, carboxylic acid groups, acyl groups (e.g., carboxylic acid derivatives such as esters and amides), amine groups, and nitro groups. For example, the 4-methylcyclopent-1-yl radical is a C6 alicyclic radical that contains a methyl group, where the methyl group is the functional group that is the alkyl group. Similarly, the 2-nitrocyclobut-1-yl radical is a C4 alicyclic radical that contains a nitro group, where the nitro group is the functional group. An alicyclic radical may contain one or more halogen atoms, which may be the same or different. Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine. Cycloaliphatic radicals containing one or more halogen atoms include 2-trifluoromethylcyclohex-1-yl, 4-bromodifluoromethylcyclooct-1-yl, 2-chlorodifluoromethylcyclohex-1-yl, hexafluoroisopropylidene-2,2-bis(cyclohex-4-yl) (i.e., -CH 10 C(CF3)2C6H 10-), 2-chloromethylcyclohex-1-yl, 3-difluoromethylenecyclohex-1-yl, 4-trichloromethylcyclohex-1-yloxy, 4-bromodichloromethylcyclohex-1-ylthio, 2-bromoethylcyclopent-1-yl, 2-bromopropylcyclohex-1-yloxy (e.g., CH3CHBrCH2CH 10 Further examples of alicyclic radicals include 4-aryloxycyclohex-1-yl, 4-aminocyclohex-1-yl (i.e., H2C6H6H2O-), and the like. 10 -), 4-aminocarbonylcyclopent-1-yl (i.e., NH2COC5H8-), 4-acetyloxycyclohex-1-yl, 2,2-dicyanoisopropylidenebis(cyclohex-4-yloxy) (i.e., -OC6H 10 C(CN)2C6H 10 O-), 3-methylcyclohex-1-yl, methylenebis(cyclohex-4-yloxy) (i.e., -OCH 10 CH2C6H 10 O-), 1-ethylcyclobut-1-yl, cyclopropylethenyl, 3-formyl-2-tetrahydrofuranyl, 2-hexyl-5-tetrahydrofuranyl, hexamethylene-1,6-bis(cyclohex-4-yloxy) (i.e., -OCH 10 (CH2)6C6H 10 O-), 4-hydroxymethylcyclohex-1-yl (i.e., 4-HOCH2C6H 10 -), 4-mercaptomethylcyclohex-1-yl (i.e., 4-HSCH2C6H 10 -), 4-methylthiocyclohex-1-yl (i.e., 4-CH3SC6H 10 -), 4-methoxycyclohex-1-yl, 2-methoxycarbonylcyclohex-1-yloxy (2-CH3OCOC6H 10 O-), 4-nitromethylcyclohex-1-yl (i.e., NO2CH2C6H 10-), 3-trimethylsilylcyclohex-1-yl, 2-t-butyldimethylsilylcyclopent-1-yl, 4-trimethoxysilylethylcyclohex-1-yl (e.g., (CH3O)3SiCH2CH2C6H 10 -), 4-vinylcyclohexen-1-yl, vinylidenebis(cyclohexyl), and the like. The term "C3-C10 cycloaliphatic radical" includes cycloaliphatic radicals containing at least 3 but not more than 10 carbon atoms. The cycloaliphatic radical 2-tetrahydrofuranyl (C4H7O-) represents a C4 cycloaliphatic radical. The cyclohexylmethyl radical (C6H 11 CH2-) represents a C7 cycloaliphatic radical. In some embodiments, the cycloaliphatic group can include a C3-C20 cyclic group, a C5-C15 cyclic group, a C6-C10 cyclic group, or a C8-C10 cyclic group.

[0015] As used herein, the terms "aliphatic", "aliphatic group" and "aliphatic radical" are used interchangeably and refer to an organic radical having at least one valence consisting of a linear or branched arrangement of atoms that is not cyclic. An aliphatic radical is defined to contain at least one carbon atom. The arrangement of atoms that comprises an aliphatic radical may contain heteroatoms such as nitrogen, sulfur, silicon, selenium, and oxygen, or may be composed exclusively of carbon and hydrogen. For convenience, the term "aliphatic radical" is defined herein to encompass a wide range of functional groups, such as alkyl groups, alkenyl groups, alkenyl groups, haloalkyl groups, conjugated dienyl groups, alcohol groups, ether groups, aldehyde groups, ketone groups, carboxylic acid groups, acyl groups (e.g., carboxylic acid derivatives such as esters and amides), amine groups, nitro groups, etc., as part of the "linear or branched arrangement of atoms that is not cyclic". For example, the 4-methylpent-1-yl radical is a C6 aliphatic radical that contains a methyl group, and the methyl group is a functional group that is an alkyl group. Similarly, the 4-nitrobut-1-yl group is a C4 aliphatic radical containing a nitro group, the nitro group being a functional group. The aliphatic radical may be a haloalkyl group containing one or more halogen atoms, which may be the same or different. Halogen atoms include, for example, fluorine, chlorine, bromine, and iodine. Aliphatic radicals containing one or more halogen atoms include alkyl halides trifluoromethyl, bromodifluoromethyl, chlorodifluoromethyl, hexafluoroisopropylidene, chloromethyl, difluorovinylidene, trichloromethyl, bromodichloromethyl, bromoethyl, 2-bromotrimethylene (e.g., -CH2CHBrCH2-), and the like.Further examples of aliphatic radicals include allyl, aminocarbonyl (i.e., -CONH), carbonyl, 2,2-dicyanoisopropylidene (i.e., -CHC(CN)CH-), methyl (i.e., -CH), methylene (i.e., -CH-), ethyl, ethylene, formyl (i.e., -CHO), hexyl, hexamethylene, hydroxymethyl (i.e., -CHOH), mercaptomethyl (i.e., -CHSH), methylthio (i.e., -SCH), methylthiomethyl (i.e., -CHSCH), methoxy, methoxycarbonyl (i.e., CHOCO-), nitromethyl (i.e., -CHNO), thiocarbonyl, trimethylsilyl (i.e., (CH)Si-), t-butyldimethylsilyl, 3-trimethoxysilylpropyl (i.e., (CHO)SiCHCHCH-), vinyl, vinylidene, and the like. As a further example, a C1-C10 aliphatic radical contains at least one but no more than 10 carbon atoms. A methyl group (i.e., CH3-) is an example of a C1 aliphatic radical. A decyl group (i.e., CH3(CH2)9-) is an example of a C10 aliphatic radical. In one or more embodiments, an aliphatic group or radical can include, but is not limited to, straight or branched chain hydrocarbons having 1-20 carbon atoms, 2-15 carbon atoms, 3-10 carbon atoms, or 4-8 carbon atoms.

[0016] The present technology provides a curable silicone-based composition and the use of such a composition in various applications. The selection of polymer A, polymer B, and one or more fillers as described herein in the composition provides a hybrid composite with versatile properties. In addition, the present composition allows the use of relatively high loadings of fillers in the silicone matrix without affecting the curing and processing conditions of the composition. The presence of non-silicone organic units can be used to provide additional benefits to the overall properties of the hybrid silicone composite. The curable silicone composition is an epoxy amine cure system; and wherein the cured form of the curable composition is a conductive material.

[0017] One or more embodiments of the present technology provide a curable composition comprising polymer A, polymer B, and one or more fillers. Polymer A comprises an organic molecule or a siloxane molecule that comprises an epoxy functional group. Polymer B comprises an organic molecule, a siloxane molecule, or a hybrid siloxane molecule that comprises an amine functional group. The curable composition of these embodiments can form a hybrid silicone composite upon curing. The hybrid silicone composite can be formed by epoxyamine curing.

[0018] In some embodiments, polymer A comprises organic molecules containing one or more epoxy functional groups, siloxane molecules containing one or more epoxy functional groups, or a combination thereof. In some embodiments, polymer A comprises organic molecules containing one or more epoxy functional groups. Epoxy-functionalized organic molecules (non-siloxane) are hereinafter referred to as "organic epoxies". In some other embodiments, polymer A comprises siloxane molecules containing one or more epoxy functional groups. Epoxy-functionalized siloxane molecules are hereinafter referred to as "siloxane epoxies". In some embodiments, the siloxane epoxy can be a linear polymer chain, where the epoxy functional groups are attached to the terminal positions of the siloxane linear polymer. In some other embodiments, the siloxane epoxy can be a branched polymer, where the epoxy functional groups are attached to one or more pendant positions of the siloxane branched polymer.

[0019] Polymer A may be selected from compounds of formula 1, (R) a (W) b (R) a’’ formula 1 where a is equal to a″ and can be 0 or greater, and b is greater than 0. R can be represented by formula (1a): (L1) c [(CH2) d (CH2O) e X] f Formula (1a) wherein L1 is a heteroatom independently selected from oxygen or nitrogen, and wherein c, e can independently be 0 or greater, and d, f are independently greater than 0, with the proviso that (d+e) is greater than 0. Further, in formula (1a), X can be independently selected from any of the functional moieties represented by formula (1b): [ka] where g, h, and i can independently be 0 or greater; j and k can independently be 0 or greater, with the proviso that (j+k) is greater than 0. R1 is an aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon, selected from the group consisting of C1-C 20 It is selected from those having carbon atoms and optionally bonded to an ester. Here, W in Equation 1 can be expressed by Equation (1c), (Y) l (Z) m Formula (1c) where l and m can be independently zero or greater, provided that l+m>0. Furthermore, Y in formula (1c) can be represented by formula (1d): (M1) n’’ (D1) n (D2) o (T1) p (Q1) q (M2) n’’’ Formula (1d) where n, o, p, q, n'', and n''' can be zero or greater, provided that n+o+p+q+n''+n''>0. Furthermore, M1 in formula (1d) is represented by formula (1e): R2R3R4SiO 1 / 2 Formula (1e) Here, D1 is expressed by formula (1f), R5R6SiO 2 / 2 Formula (1f) Here, D2 is expressed by formula (1g). R7R8SiO 2 / 2 Formula (1g) Here, T1 is expressed by formula (1h), R9SiO 3 / 2 Formula (1h) Here, Q1 is expressed by the formula (1i). SiO 4 / 2 Formula (1i) Here, M2 is expressed by equation (1j). R 10 R 11 R 12 SiO 1 / 2 Formula (1j) Here, R2-R 12 can be selected independently of R when c=0, or R2-R 12 is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having a C1-C 20 The alkyl groups may be independently selected from those having carbon atoms. Furthermore, Z in formula (1c) can be expressed by formula (1k), (A') r (B') s Formula (1k) where r and s can be zero or greater, with the proviso that (r+s) is always greater than zero. A' can be selected from the structures represented by formula (1l): R 13 (J) s’’ R 14 Formula (1l) where J is R 15 , R 16 and s''≧0; R 13 -R 16 may be zero or a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having a C1-C 20 The alkyl groups may be independently selected from those having carbon atoms. B' in formula (1k) can be selected from the structures represented by formula (1m): (CH2) t [(CHOH) u ((CHR 17 )(CH2) vO)) w ((CH2) x L2) y R 18 R 19 R 20 CR 21 ] z Formula (1m) Here, R 17 -R 21 is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, hydrogen, or a fluorinated hydrocarbon having a C1-C 20 L2 is a heteroatom independently selected from oxygen or nitrogen, and t, u, v, w, x, y, z are integers with the proviso that t+u+v+w+x+y+z>0.

[0020] In embodiments, a, a'' are 1; b is 1; and c, d, e, f of R are each independently 1, 1-10, 1-20, 5-10. g, h, i, j, k are independently 0-1, 0-5, or 0-10. l, m of W are independently 0-5. n'', n, o, p, q, n'' of Y are independently 0, 1-5, 5-10, or 10-20. r, s of Z are independently 0, 1-5, 5-10, or 10-20. s'' of A' is 0-5 or 0, 1-10. t, u, v, w, x, y, z of B' are independently 0, 1-2, 1-5, 5-10, or 10-20.

[0021] In one or more embodiments, polymer A can be represented by the following structure, where n can be 1-10: [ka]

[0022] For example, when n=1, polymer A can be represented by: [ka]

[0023] In one or more embodiments, polymer A can be further represented by the following structure, where n, o can be 1-10: [ka]

[0024] In an exemplary embodiment, when n=10 and m=15, polymer A can be represented by: [ka]

[0025] In an exemplary embodiment, when n=27, polymer A can be represented by: [ka]

[0026] In an exemplary embodiment, polymer A can also be represented by the following structure: [ka]

[0027] In an exemplary embodiment, where n, o can be 1-30, 1-40, or 1-50, polymer A can be represented by: [ka]

[0028] In an exemplary embodiment, polymer A can also be represented by the following structure: [ka]

[0029] In one or more embodiments, polymer B comprises an organic amine, a silicone amine, or a combination thereof. In some embodiments, polymer B comprises both organic units and silicone units with two or more amine functional groups. In some embodiments, the silicone amine is a hybrid silicone amine. Hybrid silicone amines generally comprise a combination of one or more silicone units with two or more amine functional groups and one or more non-silicone (organic) units. In such embodiments of hybrid silicone amines, each of the silicone units and each of the organic units may be arranged in an alternating manner. In another embodiment of the hybrid silicone amine, two or more silicone units are separated by one or more organic units. In some embodiments, the amine functional group may be in a terminal position. In some other embodiments, the amine functional group may be in the siloxane polymer chain of the silicone amine or in a pendant position of the hybrid silicone amine polymer.

[0030] Polymer B of the curable composition can, in embodiments, be represented by a compound of formula 2: (R') a’ (W') b’ (R') a’ Formula (2) where a', b' can be 0 or greater, and (a'+b') is greater than 0; R' can be represented by formula (2a): (CH2) c’ (OCH2CHR 22 ) d’ (R 23 L3R 24 ) e’ Formula (2a) c', e' are greater than 0, and d' may be zero or greater, provided that c'+d'+e'>0; L3 is nitrogen, and L3 can be absent, provided that e' is 0; R 22 -R 24is hydrogen, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C1-C 20 can be independently selected from those having carbon atoms, R 23 , R 24 may independently be 0 or greater, where (R 23 +R 24 ) is greater than 0, W' in Equation 2 can be expressed by Equation (2b): (Y') f’ (Z') g’ Formula (2b) f' and g' are greater than 0, and (f'+g') is greater than 0. Y' can be expressed by Equation 2c, (M3) r’ (D3) h’ (D4) i’ (T2) j’ (Q2) k’ (M4) s’ Formula (2c) h', i', r', s', j', and k' can be zero or greater, provided that (h'+i'+r'+s'+j'+k')>0. M3 is expressed by formula (2d), R 25 R 26 R 27 SiO 1 / 2 Formula (2d) D3 is expressed by formula (2e), R 28 R 29 SiO 2 / 2 Formula (2e) D4 is represented by formula (2f), R 30 R 31 SiO 2 / 2 Formula (2f) T2 is represented by formula (2g), R 32 SiO 3 / 2 Formula (2g) Q2 is expressed by formula (2h), SiO 4 / 2 Formula (2h) M4 is expressed by formula (2i), R 33 R 34 R 35 SiO 1 / 2 Formula (2i) Here, R 25 -R 35 is R', or hydrogen, hydroxyl, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C1-C 20 The alkyl groups may be independently selected from those having carbon atoms. Z' in formula (2b) can be expressed by formula (2j), R 36 L4(CH l’ ) m’ R 37 L5(CH n’ ) o’ L6R 38 (CH p’ ) q’ Formula (2j) Z′ in formula (2j) can be linear or cyclic, where R 36 -R 38 is R' or hydrogen, or a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon, optionally bonded through a heteroatom, C-C 20 may be independently selected from those having carbon atoms or halogens; L4, L5, or L6 are heteroatoms independently selected from oxygen or nitrogen; L4, L5, or L6 may be 0 or greater, provided that (L4+L5+L6) is greater than or equal to 0; l', m', n', o', p', and q' are integers, provided that l'+m'+n'+o'+p'+q'>0.

[0031] In embodiments, a', b' are 1, and c', e', d' of R' are each independently 1-10, 1-10, 0-10. f', g' of W are independently 0-10. h', i', r', s', j', k' of Y' are independently 0-10. l', m', n', o', p', q' of Z' are independently 0-10.

[0032] In one or more embodiments, polymer B can be represented by the following, where n can be 1-5, 1-10, 1-20: [ka]

[0033] In formula 2, a' is 0 and b' is 1. Also in formula 2a, c' and d' are 0 and e' is 2. In formula 2b, f' is 0 and g' is 1. In formula 2j, R 36 is R', and as a constraint, d' is 3 in R', and R 22 is methyl, and c' and e' are 0. Furthermore, in formula 2j, L4, L5 and L6 are absent, while i', m', n', o' are 1, and R 37 is methyl. 38 is selected from R', with the constraints that c', d', and e' are 0.

[0034] In one or more embodiments, polymer B can be represented by the following structure, where m or n can be 1-5, 1-10, or 1-20. [ka]

[0035] Various weight ratios of polymer A and polymer B are added to the composition to achieve desired properties for the hybrid composite. In one or more embodiments, the curable composition comprises polymer A in the range of about 5% to 60%. In some embodiments, the curable composition comprises polymer A in the range of about 8% to 50%. In some embodiments, the curable composition comprises polymer A in the range of about 10% to 60%. In some embodiments, the curable composition comprises polymer A in the range of about 20% to 50%. In some embodiments, the curable composition comprises polymer A in the range of about 15% to 60%. In some embodiments, the curable composition comprises polymer A in the range of about 25% to 50%.

[0036] In some embodiments, the curable composition comprises polymer A in the range of about 5% to 25%. As used herein, percentage of polymer A is a weight percent based on the total weight of the composition. In one or more embodiments, the curable composition comprises polymer B in the range of about 5% to 30%. In some embodiments, the curable composition comprises polymer B in the range of about 8% to 30%. In some embodiments, the curable composition comprises polymer B in the range of about 10% to 20%. In some embodiments, the curable composition comprises polymer B in the range of about 7% to 20%.

[0037] In some embodiments, the curable composition comprises about 5% to 20% of polymer B. In some embodiments, the curable composition comprises about 8% to 18% of polymer B. In some embodiments, the curable composition comprises about 5% to 15% of polymer B. As used herein, percentages of polymer B are weight percents based on the total weight of the composition.

[0038] As previously mentioned, the composition includes one or more fillers, where the fillers include, but are not limited to, alumina, silicon, magnesia, ceria, hafnia, lanthanum oxide, neodymium oxide, samaria, praseodymium oxide, thoria, urania, yttria, zinc oxide, zirconia, silicon aluminum oxynitride, borosilicate glass, barium titanate, silicon carbide, silica, boron carbide, titanium carbide, zirconium carbide, boron nitride, silicon nitride, nitride. Aluminum, titanium nitride, zirconium nitride, zirconium boride, titanium diboride, aluminum dodecaboride, barite, barium sulfate, asbestos, barite, diatomite, feldspar, gypsum, hormite, kaolin, mica, nepheline, perlite, phyllophyllite, smectite, talc, vermiculite, zeolite, calcite, calcium carbonate, wollastonite, calcium metasilicate, clay, aluminum silicate, talc, aluminum silicate The present invention may be used in a wide variety of applications, including but not limited to, titanium dioxide, magnesium, hydrated alumina, hydrated aluminum oxide, silica, silicon dioxide, titanium dioxide, glass fiber, glass flakes, clay, exfoliated clay, or other high aspect ratio fibers, rods, or flakes, calcium carbonate, zinc oxide, magnesia, titania, calcium carbonate, talc, mica, wollastonite, alumina, aluminum nitride, graphite, graphene, metal coated graphite, metal coated graphene, aluminum powder, copper powder, bronze powder, brass powder, fibers or whiskers of carbon, graphite, silicon carbide, silicon nitride, alumina, aluminum nitride, silver, zinc oxide, carbon nanotubes, boron nitride nanosheets, zinc oxide nanotubes, black phosphorus, silver coated aluminum, silver coated glass, silver plated aluminum, nickel plated silver, nickel plated aluminum, carbon black of different structures, Monel mesh and wire, or a combination of two or more thereof.

[0039] In one or more embodiments, the filler comprises graphite, nickel-coated graphite, silver, copper, or a combination thereof. In one or more embodiments, the filler comprises graphite, nickel-coated graphite, or a combination thereof. In one embodiment, the filler is nickel-coated graphite.

[0040] To achieve the desired properties for the hybrid composite, various weight ratios of fillers are added to the composition. In one or more embodiments, the hardenable composition comprises a filler in the range of about 5% to 80%. In some embodiments, the hardenable composition comprises a filler in the range of about 20% to 80%. In some embodiments, the hardenable composition comprises a filler in the range of about 20% to 60%. In some embodiments, the hardenable composition comprises a filler in the range of about 30% to 80%. In some embodiments, the hardenable composition comprises a filler in the range of about 30% to 60%. In some embodiments, the hardenable composition comprises a filler in the range of about 50% to 80%. In some embodiments, the hardenable composition comprises a filler in the range of about 60% to 80%. The amount of filler described herein refers to a weight percentage based on the total weight of the composition.

[0041] In some embodiments, the curable composition further comprises an adhesion promoter selected from a trialkoxyepoxy silane, a trialkoxy primary amino silane, a combination of primary and secondary amine-containing trialkoxy silanes, a tris-(trialkoxy)isocyanurate-based silane, an alkylthiocarboxylated trialkoxy silane, or a combination of two or more thereof.

[0042] In some embodiments, the curable composition further comprises a reactive diluent. The reactive diluent may include, but is not limited to, a substituted glycidyl ether. The reactive diluent may include one or more solvents. Suitable solvents may include, but are not limited to, liquid hydrocarbons or silicone fluids. The hydrocarbon solvent may include hexane or heptane, and the silicone fluid may include polydiorganosiloxane.

[0043] In some embodiments, the curable composition further comprises rheology modifier or flow additive.Rheology modifier can include, but is not limited to, tetrahydrolinalool, thermoplastic resin, and polyvinyl acetal.Flow additive can include, but is not limited to, silicone fluid or acrylate copolymer.

[0044] In some embodiments, silicone multi-epoxy compounds of different chain lengths were synthesized by re-equilibrating Silforce*UV9315 (Momentive Performance Materials) with an appropriate amount of octamethylcyclotetrasiloxane under basic conditions using tetrabutylammonium hydroxide at 90° C. In some embodiments, silicone multi-epoxy compounds of different chain lengths (pendant) were synthesized by hydrosilylation of vinylcyclohexene oxide with an appropriate amount of silicone fluid having pendant hydrides using Karstedt's catalyst at 75° C.

[0045] In some embodiments, polymer A, polymer B, and filler are mixed together in terms of their epoxy and amine equivalent weights. The mixture is homogenized using a Hauschild speed mixer at 2350 rpm for 120 seconds. In one or more embodiments, the composition is cured by epoxy-amine curing between 40-80° C. In one embodiment, the homogenized mixture is cured at 60° C. in a hot air oven.

[0046] In some embodiments, the applications of the cured materials and their end uses are coatings, adhesives, sealants, electrodes, inks, thermally conductive materials, electrically conductive materials, sensors, actuators, heating pads, antimicrobial packaging materials, conductive plastics, electromagnetic shielding materials.

[0047] This written description uses examples to disclose the invention, including the best mode, and also to enable any person skilled in the art to practice the invention, including making and using any devices or systems and performing any integration methods. The patentable scope of the invention is defined by the claims, and may include other examples that occur to those skilled in the art. Such other examples are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements that do not differ substantially from the literal language of the claims. EXAMPLES

[0048] Example 1: Synthesis of multiepoxysiloxane (Polymer A) 10 g of Silforce*UV9315 (Momentive Performance Materials) was placed in a 3-neck round bottom flask. To it, 130 g of D4 was added. To it was further charged 2500 ppm of tetrabutylammonium hydroxide. The reaction mixture was gently heated from room temperature to 90°C and a full vacuum of 1 mbar was applied for the first 30 minutes. Then, the vacuum was turned off and heated with stirring at 90°C for 6 hours until a solid content of 93% was achieved. The contents were heated to 135°C to deactivate the catalyst and remove excess D4. The product (A3) was further isolated and stored.

[0049] Example 2: Synthesis of pendant epoxy siloxane (Polymer A) Based on the degree of polymerization, a siloxane-based silicone polymer with 10 pendant hydrogens, 15 SiOMe2 units, and SiMe3 capping was placed in a three-neck round-bottom flask and kept stirring above 75°C. At the desired temperature, 10 ppm of Pt catalyst was added to the round-bottom flask and allowed to mix homogeneously. Then, 4-vinyl-1-cyclohexane 1,2-epoxide was placed in a dropping funnel and added dropwise to the reaction mixture of hydride and catalyst. The ratio of vinyl to hydride was considered to be 1.05:1. Product A4 was further isolated and stored. [ka]

[0050] Example 3: Synthesis of terminal epoxy siloxane (Polymer A) Based on the degree of polymerization, a bis-terminated hydrogen, siloxane-based silicone polymer with 27 SiOMe2 units was placed in a three-neck round-bottom flask and kept stirring at 75°C or higher. At the desired temperature, 10 ppm of Pt catalyst was added to the round-bottom flask and mixed homogeneously. Then, 4-vinyl-1-cyclohexane 1,2-epoxide was placed in a dropping funnel and added dropwise to the reaction mixture of hydride and catalyst. The vinyl to hydride ratio was deemed to be 1.05:1. Product A5 was further separated and stored. [ka]

[0051] Example 4: Synthesis of cyclic epoxysiloxane (Polymer A) Based on the degree of polymerization, tetramethylcyclotetrasiloxane was placed in a three-neck round bottom flask and kept stirring above 75°C. At the desired temperature, 10 ppm of Pt catalyst was added to the round bottom flask and allowed to mix homogeneously. Then, allyl glycidyl ether was placed in a dropping funnel and added dropwise to the reaction mixture of hydride and catalyst. The vinyl to hydride ratio was deemed to be 1.05:1. Product A6 was further isolated and stored. [ka]

[0052] Table 1 provides the above structure (1-III) as well as a description and source of the various materials used in the formulation. [Table 1] **Labels are used herein to describe formulations. *Momentive commercial product.

[0053] Preparation of various formulations Hybrid silicone composites were prepared in the presence of one or more fillers using polymer A containing one or more epoxy functional groups and polymer B containing two or more amine functional groups, where the amine functional groups can be either at the end or pendant of the siloxane molecule. Various weight ratios of fillers were added to the mixture of polymer A and polymer B. Polymer A, polymer B and fillers were mixed and then cured at 60°C. Both epoxy-functional polymer A and amine-functional polymer B were added in equimolar ratios based on their equivalent weights. Details of the various formulations are shown in Table 1 below. For the various formulations, various types of silicone epoxy, organic epoxy, silicone amine, hybrid silicone amine, and organic amine, and various types of fillers were selected. For example, in formulations 1 and 2, EPON828 (Hexion), an organic bis-epoxy molecule, was used as polymer A with pendant amino silicone as polymer B in the presence of nickel-coated graphite as filler. Similarly, for formulations 3 to 6, Heloxy62 (Hexion), an organic mono epoxy molecule, was used with EPON828 as polymer A with pendant amino silicone as polymer B in the presence of nickel coated graphite as filler. In formulations 7 and 8, trimethoxy epoxy silane was added as an adhesion promoter to components such as EPON828, pendant amino silicone, and nickel coated graphite. In formulations 9 and 10, EPON828 was used as polymer A with pendant amino silicone as polymer B in the presence of graphite as filler. In formulation 11, vinylcyclohexane multi-epoxy PDMS (SE2) was used as polymer A with JeffamineD230 (Huntsman) as polymer B in the presence of nickel coated graphite as filler. The various formulations are shown in Table 2. Various types of epoxy functionalized silicones, epoxy functionalized organic polymers, and organic amines, or silicone amines, were used and are shown below. [ka]

[0054] The details of the different formulations are given in Table 2 below. For the different formulations, different types of silicone epoxy, organic epoxy, hybrid silicone epoxy, silicone amine, and hybrid silicone amine were selected. [Table 2]

[0055] Test methodology for physical and mechanical properties Electrical Conductivity Measurement: Electrical resistivity measurements of the samples of various morphologies were carried out as per ASTM D257 standard using a four-probe setup. The obtained electrical resistivity values ​​were converted into electrical conductivity. Lap shear of the developed formulations was measured using ASTM D3163 standard. Instron equipment was also used as well. Hardness Measurement: Hardness of the developed composites was measured as per ASTM D2240 standard. [Table 3] ND: Not determined

[0056] EMI Shielding Measurement: EMI shielding measurements of samples with different configurations were performed according to IEEE299 standard. The EMI shielding ability of the developed formulations was also confirmed in the range of 6 GHz to 12 GHz. The thickness of the samples was between 0.5 mm and 1.5 mm. The EMI shielding effectiveness of selected samples is shown in Table 4. [Table 4]

[0057] Thermal Conductivity: Thermal conductivity measurements of the samples were performed according to ASTM E1530 standard. The thermal conductivity of selected samples is shown in Table 5. [Table 5]

[0058] Comparative Example 1 To show a comparison between the hybrid silicone-based formulations and the purely organic-based formulations, a control sample (compared to formulation F7) was prepared and tested. [Table 6]

[0059] The embodiments of the present technology have been described above, and modifications and alterations may occur to others upon reading and understanding this specification. It is intended that the following claims include all modifications and alterations insofar as they come within the scope of the claims or equivalents thereof.

Claims

1. 1. A curable silicone composition comprising: (i) an epoxy-functional polymer A of formula 1; (ii) an amine-functional polymer B of formula 2, which contains one or more amine functional groups; and (iii) an electrically conductive filler; wherein the curable silicone composition is an epoxy amine cure system; and wherein the curable composition is in a cured form to form a conductive material, and wherein polymer (A) is of formula 1 (R) ａ (W) ｂ (R) ａ’’ Formula (1) where b is greater than 0, a and a″ are 0 or greater, and (a+a″) is greater than 1; R can be represented by formula (1a): (L １ ) ｃ [(CH ２ ) ｄ (CH ２ O) ｅ X] ｆ Formula (1a) Here, L １ are heteroatoms independently selected from oxygen or nitrogen, and where c, e can be 0 or greater, and d, f are greater than 0, with the proviso that (d+e) is greater than 0; X is independently selected from any of the functional moieties represented by formula (1b): [Formula 1] where g, h, i are 0 or greater; j and k are 0 or greater, with the proviso that (j+k) is greater than 0; R １ is selected from an aliphatic or aromatic substituted hydrocarbon, or an unsubstituted hydrocarbon, or a fluorinated hydrocarbon having 1-20 carbon atoms and optionally linked to an ester; W in formula 1 can be expressed by formula (1c): (Y) ｌ (Z) ｍ Formula (1c) where l and m are zero or greater, provided that l+m>0; Y in formula (1c) is represented by formula (1d): (M １ ) ｎ’’ (D １ ) ｎ (D ２ ) ｏ (T １ ) ｐ (Q １ ) ｑ (M ２ ) ｎ’’’ Formula (1d) where n, o, p, q, n'', and n''', are zero or greater, provided that n+o+p+q+n''+n''',>0; M １ is selected from formula (1e): R ２ R ３ R ４ SiO １／２ Formula (1e) D １ is selected from formula (1f), R ５ R ６ SiO ２／２ Formula (1f) D ２ is selected from formula (1g), R ７ R ８ SiO ２／２ Formula (1g) T １ is selected from formula (1h), R ９ SiO ３／２ Formula (1h) Q １ is selected from formula (1i): SiO ４／２ Formula (1i) M ２ is selected from formula (1j), R １０ R １１ R １２ SiO １／２ Formula (1j) Here, R ２ -R １２ is selected independently from R with the proviso that c=0; or ２ -R １２ is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or fluorinated hydrocarbon having C １ -C ２０ are independently selected from those having carbon atoms; Z is represented by the formula (1k) (A') ｒ (B') ｓ Formula (1k) where r and s can be zero, provided that (r+s) is always greater than zero. A' is selected from formula (1l): R １３ (J) ｓ’’ R １４ Formula (1l) Here J is R １５ and R １６ and s″≧0; R １３ -R １６ are independently selected from monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbons, or fluorinated hydrocarbons having 1-20 carbon atoms; B' is selected from the structure of formula (1m): (CH ２ ) ｔ [(CHOH) ｕ ((CHR １７ ) (CH ２ ) ｖ O) ｗ ((CH ２ ) ｘ L ２ ) ｙ R １８ R １９ R ２０ CR ２１ ] ｚ Formula (1m) Here, R １７ -R ２１ is a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, hydrogen, or a fluorinated hydrocarbon having C １ -C ２０ carbon atoms; L ２ are heteroatoms independently selected from oxygen or nitrogen, and t, u, v, w, x, y, z are integers with the proviso that t+u+v+w+x+y+z>0; Polymer B is of formula 2: (R') ａ’ (W') ｂ’ (R') ａ’ Formula (2) wherein a' and b' are independently 0 or greater, with the proviso that (a' + b') is greater than 0; and R' is of formula (2a): (CH ２ ) ｃ’ (O.C.H. ２ CHR ２２ ) ｄ’ (R ２３ L ３ R ２４ ) ｅ’ Formula (2a) where c' and e' are independently greater than 0, and d' may be zero or greater, provided that c'+d'+e'>0; L ３ is nitrogen, L ３ may be 0 or greater, R ２２ -R ２４ is hydrogen, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having a C １ -C ２０ are independently selected from those having carbon atoms; R ２３ , R ２４ are independently 0 or greater, where (R ２３ +R ２４ ) is greater than 0, W′ is of formula (2b), (Y′) ｆ’ (Z′) ｇ’ Formula (2b) where f' and g' are 0 or greater, and (f'+g') is greater than 0; Y' is of formula 2c, (M ３ ) ｒ’ (D ３ ) ｈ’ (D ４ ) ｉ’ (T ２ ) ｊ’ (Q ２ ) ｋ’ (M ４ ) ｓ’ Formula (2c) where h', i', r', s', j', and k' may be zero or greater, provided that (h'+i'+r'+s'+j'+k')>0; M ３ is selected from formula (2d): R ２５ R ２６ R ２７ SiO １／２ Formula (2d) D ３ is selected from formula (2e): R ２８ R ２９ SiO ２／２ Formula (2e) D ４ is selected from formula (2f), R ３０ R ３１ SiO ２／２ Formula (2f) T ２ is selected from formula (2g), R ３２ SiO ３／２ Formula (2g) Q ２ is selected from formula (2h), SiO ４／２ Formula (2h) M ４ is selected from formula (2i) R ３３ R ３４ R ３５ SiO １／２ Formula (2i) R ２５ -R ３５ is R′, hydrogen, a hydroxyl radical, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon having C １ -C ２０ are independently selected from those having carbon atoms; Z′ is of formula (2j), R ３６ L ４ (CH ｌ’ ) ｍ’ R ３７ L ５ (CH ｎ’ ) ｏ’ L ６ R ３８ (CH ｐ’ ) ｑ’ Formula (2j) where Z' is linear or cyclic; R ３６ -R ３８ is R′ or hydrogen, a monovalent cyclic or acyclic, aliphatic or aromatic, substituted or unsubstituted hydrocarbon, or a fluorinated hydrocarbon, optionally bonded through a heteroatom; １ -C ２０ independently selected from those having carbon atoms or halogens; L ４ , L ５ , or L ６ is a heteroatom independently selected from oxygen or nitrogen; L ４ , L ５ , or L ６ can be 0 or greater, where (L ４ +L ５ +L ６ ) is greater than or equal to 0, and l', m', n', o', p', and q' are independently selected from positive integers, with the proviso that l'+m'+n'+o'+p'+q'>0; wherein the cured form of the curable composition has an electromagnetic interference (EMI) shielding effectiveness of between 50 and 170 dB; A curable silicone composition.

2. 10. The curable silicone composition of claim 1, wherein the one or more amine functional groups of Polymer B are located at terminal positions, pendant positions, or both terminal and pendant positions.

3. 3. The curable silicone composition of claim 1, wherein Polymer A is present in the range of about 5% to about 60% by weight, based on the total weight of the composition.

4. 4. The curable silicone composition of claim 1, wherein Polymer B is present in the range of about 5% to about 30% by weight, based on the total weight of the composition.

5. 5. The curable silicone composition of any one of claims 1 to 4, wherein the electrically conductive filler is selected from the group consisting of graphite, graphene, metal coated graphite, metal coated graphene, aluminum powder, copper powder, bronze powder, brass powder, carbon fibers or whiskers, graphite, silicon carbide, silicon nitride, silver, zinc oxide, carbon nanotubes, boron nitride nanosheets, zinc oxide nanotubes, black phosphorus, silver coated aluminum, silver coated glass, silver plated aluminum, nickel plated silver, nickel plated aluminum, carbon black of different structures, Monel mesh and wire, or a combination of two or more thereof.

6. 6. The curable silicone composition of claim 5, wherein the weight ratio of the filler added to the composition ranges from about 5% to 80% by weight, based on the total weight of the composition.

7. 7. The curable silicone composition of claim 1, wherein polymer B is selected from a linear polymer, a branched polymer, or a cyclic structure.

8. The curable silicone composition of claim 1 , wherein polymer B is a branched polymer.

9. 9. The curable silicone composition of claim 1, further comprising a catalyst or supported catalyst selected from an acid, a base, a Lewis acid, an ammonium salt, or a combination of two or more thereof.

10. 10. The curable silicone composition of any one of claims 1 to 9, further comprising an adhesion promoter selected from the group consisting of trialkoxyepoxy silanes, trialkoxy primary amino silanes, combinations of primary and secondary amine-containing trialkoxy silanes, tris-(trialkoxy)isocyanurate-based silanes, alkylthiocarboxylated trialkoxy silanes, alkenyl silanes, acrylated silanes, acrylated alkoxy silanes, fumarate-based alkoxy silanes, carboxyl-functional silanes, epoxy-vinyl silanes, hydroxy-functional organosilanes, anhydride-functional silanes, amide-functional alkoxy silanes, titanates, zirconates, organic anhydrides and carboxylates, halogenated organic compounds, organic acrylates, or combinations of two or more thereof.

11. 11. The curable silicone composition of claim 1, further comprising a reactive diluent selected from the group consisting of substituted glycidyl ethers, hexanes, heptanes, polydiorganosiloxanes, or combinations of two or more thereof.

12. 12. The curable silicone composition of any one of claims 1 to 11, further comprising a rheology modifier selected from the group consisting of alkanes, silanes, silicones, acrylic copolymers, glycols, polyols, ethers, esters, polyesters, alcohols, amides, polyamides, amines, polyamines, imines, polyimines, urethanes, polyurethanes, ketones, polyketones, sugars, polysaccharides, cellulose, fluorinated compounds, thermoplastic or thermoset resins, polyvinyl compounds, synthetic or natural oils, natural additives, guar, xanthan, alginates, lactates, lactides, anhydrides, gums, silicates, borates, oxides, sulfides, sulfates, or combinations of two or more thereof.

13. A cured material formed from the composition of any one of claims 1 to 12.

14. 14. The curable material of claim 13, wherein the curable material is thermally conductive, electrically conductive, or a combination thereof.

15. 14. The curable material of claim 13, wherein the curable material has an electromagnetic interference (EMI) shielding effectiveness of between 50 and 170 dB.

16. 14. The cured material of claim 13, wherein the cured material is in the form of a coating, an adhesive, a sealant, an electrode, an ink, a thermally conductive material, an electrically conductive material, a sensor, an actuator, a heating pad, an antimicrobial packaging material, a conductive plastic, or an electromagnetic shielding material.

17. 13. A method of making a silicone composition comprising mixing the compositions of any of claims 1 to 12, homogenizing the mixture to form a homogenized mixture, and curing the homogenized mixture by epoxy amine curing, wherein polymer A and polymer B are silicone polymers.

18. (i) mixing together a polymer A containing two or more epoxy functional groups, a polymer B containing two or more amine functional groups, and one or more electrically conductive fillers in terms of the epoxy equivalents of polymer A and the amine equivalents of polymer B to form a mixture; (ii) then homogenizing the mixture to form a homogenized mixture; and (iii) the homogenized mixture is then cured by epoxy amine curing. A method for making the silicone composition of any of claims 1 to 12.

Images