Imide-functional organopolysiloxanes

Abstract

Imide functional organopolysiloxanes are shown and described herein. The imide-functional organopolysiloxane comprises a plurality of functional groups, and in an embodiment, at least an imide functional group and an epoxy functional group. Also provided is a composite material comprising an imide functional organopolysiloxane.

Description

Technical Field

[0001] This invention relates to imide-functionalized organopolysiloxanes. In particular, this invention relates to imide-functionalized organopolysiloxanes modified with imide and / or epoxy functional groups. Background Technology

[0002] Silicone materials are used in a wide variety of applications. They exhibit a broad range of properties that make them suitable for specific applications. They can be used, for example, as additives to impart specific properties to polymer systems. For instance, silicone materials can provide compositions with flexibility, thermal stability, strength, optical transparency, etc. However, not all silicone materials achieve the same results and are suitable for all applications. In particular, achieving a combination of properties such as high curability, low thermal expansion, and high thermal stability in silicone materials is challenging. Silicone materials with this combination of properties are needed. Summary of the Invention

[0003] The following is an overview of this disclosure to provide a basic understanding of some aspects. This summary is not intended to identify key or essential elements, nor is it intended to limit the embodiments or any limitations of the claims. Furthermore, this summary provides a simplified overview of some aspects that can be described in more detail in other parts of this disclosure.

[0004] An imide-functionalized organopolysiloxane is provided. The imide-functionalized organopolysiloxane comprises an imide functional group and an epoxy functional group. In embodiments, the imide and / or epoxy functional groups may be side-attached to the siloxane chain. In other embodiments, the imide-functionalized organopolysiloxane may include an imide group bridging the siloxane unit.

[0005] A method for preparing imide-functional organopolysiloxanes is also provided. In embodiments, the corresponding imide and epoxy functional groups are introduced into the siloxane via hydrosilylation reactions with the siloxane. In embodiments, the reaction comprises an alkenyl-functional imide and a hydride-functional siloxane, wherein the alkenyl-functional imide reacts with the hydride-functional siloxane to form an imide-functional siloxane. The imide-functional siloxane with residual hydride functional groups is then reacted with an alkenyl-functional epoxy group to provide an imide-functional organopolysiloxane. In further embodiments, alkenyl-functional aromatic or aliphatic groups can also be introduced into the imide-functional organopolysiloxane via hydrosilylation.

[0006] In another aspect, a method for preparing imide-functionalized organopolysiloxanes is provided, comprising reacting a dianhydride, a diamino or dianhydride-functionalized siloxane, and an aliphatic or aromatic-functionalized amine in a one-pot reaction.

[0007] In one aspect, a siloxane is provided comprising an imide functional group and at least one functional group selected from epoxy, hydride, aromatic, aliphatic, amine, and / or acryloyl or acryloyloxy groups, wherein the siloxane is selected from linear siloxanes and nonlinear siloxanes, wherein the nonlinear siloxane comprises at least two of the functional groups selected from epoxy, hydride, aromatic, aliphatic, amine, and / or acryloyl or acryloyloxy groups.

[0008] In one embodiment, the siloxane is according to formula (I).

[0009]

[0010] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 and R 14 Each group is independently selected from hydrogen, C1-C15 alkyl, epoxy, C6-C30 aromatic groups, and imide groups, provided that (i) R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from an imide group, and (ii) R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from epoxy groups;

[0011] A1, A2, A3, and L1, L2, L3, L4, L5, L6, L7, L8, L9, L 10 L 11 and L 12 Each of these is a linking group independently selected from divalent alkyl, divalent alkenyl, and divalent ether groups;

[0012] o≥1;

[0013] w, x, y and z are each ≥ 0, where (w+x+y+z) ranges from 1 to 60;

[0014] k1, k2, k3, k4, k5, k6, k7, k8, k9, k10, k11, and k12 are each independently ≥ 0; and

[0015] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from imide, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from epoxy groups, and R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from C6-C30 aromatic groups.

[0016] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and R 12 Independently selected from hydrogen, C1-C15 alkyl groups and C6-C30 aromatic groups, R 13 Selected from imide functional groups, and R 14 Selected from epoxy functional groups.

[0017] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 Each is independently selected from hydrogen and C1-C15 alkyl groups, and R 13 and R 14 Selected from substituted or unsubstituted diimides.

[0018] In one embodiment according to any of the foregoing embodiments, the imide group is selected from groups of formulas (IV), (V), and (VI):

[0019] (IV);

[0020] (V);

[0021] (VI)

[0022] Where R 18 R 19 R 20 and R 21 Independently selected from C2 to C30 divalent organic groups, and R 22 Selected from bonds, C1-C30 divalent organic groups, or O atoms.

[0023] In another aspect, a method for forming an imide-functionalized organopolysiloxane is provided, the method comprising:

[0024] (i) reacting an alkenyl-functionalized imide with a hydride-functionalized siloxane to produce an imide-functionalized siloxane, wherein the imide-functionalized siloxane contains an unreacted hydride group, and

[0025] (ii) Reacting an imide-functionalized siloxane having an unreacted hydride group with an alkenyl-functionalized epoxy group to provide an imide-functionalized organopolysiloxane comprising an imide and an epoxy functional group.

[0026] In one embodiment, the method further includes (iii) reacting an imide-functionalized siloxane having an unreacted hydride group with an alkenyl-functionalized aromatic group and / or aliphatic group to provide an imide-functionalized organopolysiloxane comprising an imide and an aromatic or aliphatic substituent.

[0027] In one implementation, step (ii) is performed after step (i).

[0028] In one embodiment, step (iii) follows step (i), and step (ii) follows step (iii) (step (ii) follows step (i)), wherein an imide-functionalized organopolysiloxane having unreacted hydride groups comprising imide and aromatic and / or aliphatic substituents reacts with an alkenyl-functionalized epoxy group to provide an imide-functionalized organopolysiloxane comprising imide, aromatic and / or aliphatic substituents and epoxy functional groups.

[0029] In one embodiment of the method according to any of the foregoing embodiments, an imide and an epoxy group are introduced into the backbone or side-mounted position of the imide-functional organopolysiloxane.

[0030] In one embodiment, an imide, an epoxy group, and an aromatic or aliphatic group are introduced into the main chain or side position of the imide-functional organopolysiloxane.

[0031] In one embodiment of the method according to any of the foregoing embodiments, each reaction under (i) and (ii) is carried out in the presence of a hydrosilylation catalyst.

[0032] On the other hand, a method for forming an imide-functional organopolysiloxane is provided, comprising: adding an aliphatic or aromatic substituted dianhydride; a diamino or dianhydride-functionalized siloxane; and an aliphatic or aromatic-functionalized amine in a one-pot reaction to produce an imide-functionalized organopolysiloxane comprising one or more substituents.

[0033] In another aspect, a composite material is provided which comprises an imide-functionalized organopolysiloxane of any of the foregoing embodiments.

[0034] In one embodiment, the composite material further comprises a functional polymer / resin capable of reacting with an imide-functional organopolysiloxane, and a catalyst.

[0035] The following description and figures disclose various illustrative aspects. Some improvements and novel aspects may be clearly identified, although others are obvious from the description and figures. Detailed Implementation

[0036] Exemplary embodiments and examples illustrated in the accompanying drawings will now be mentioned. It should be understood that other embodiments may be utilized, and structural and functional changes may be made. Furthermore, features of various embodiments may be combined or modified. Therefore, the following description is presented only by illustrative means and should not in any way limit the various substitutions and modifications that may be made to the illustrated embodiments. Numerous specific details in this disclosure provide a thorough understanding of the subject matter. It should be understood that aspects of this disclosure may be practiced through other embodiments, which do not necessarily include all aspects described herein.

[0037] As used herein, the terms “example” and “exemplary” mean instance or illustration. The terms “example” or “exemplary” do not indicate key or preferred aspects or implementations. Unless the context otherwise requires, the word “or” is intended to indicate inclusion rather than exclusivity. For example, the phrase “A employs B or C” includes any inclusive permutation (e.g., A employs B; A employs C; or A employs both B and C). Furthermore, unless the context otherwise requires, the article “a” generally means “one or more”.

[0038] As used herein, the term "organic group" generally refers to an acyclic, cyclic (or alicyclic), and aromatic carbonyl group, which may be saturated or unsaturated and may optionally be substituted or interrupted by one or more atoms or functional groups (e.g., carboxyl, cyano, hydroxyl, halogen, and oxygen). It should be understood that the term may encompass monovalent, divalent, and trivalent groups, and indicates and anticipates the appropriate type of bonding group within the context of the bonding of organic groups in a given formula or structure.

[0039] As used herein, the term "acyclic organic group" refers to a straight-chain or branched carbon-based group, preferably each containing 1 to 60 carbon atoms, which may be saturated or unsaturated, and may optionally be substituted or interrupted by one or more atoms or functional groups, such as carboxyl, cyano, hydroxyl, halogen, and oxygen. Suitable monovalent acyclic organic groups include, for example, alkyl, alkenyl, alkynyl, hydroxyalkyl, cyanoalkyl, carboxylalkyl, alkoxy, oxaalkyl, alkylcarbonyloxaalkylene, formamide, and haloalkyl, such as methyl, ethyl, sec-butyl, tert-butyl, octyl, decyl, dodecyl, cetyl, stearyl, vinyl, propenyl, butynyl, hydroxypropyl, cyanoethyl, butoxy, 2,5,8-trioxadecyl, carboxymethyl, chloromethyl, and 3,3,3-fluoropropyl.

[0040] As used herein, the term "alicyclic organic group" refers to a carbonyl group containing one or more saturated hydrocarbon rings, preferably each ring containing 4 to 12 carbon atoms, each group optionally being substituted with one or more alkyl groups on one or more rings, each alkyl group preferably containing 2 to 6 carbon atoms, a halogen group, or other functional group, and in the case of monovalent alicyclic organic groups containing two or more rings, they may be fused rings. Suitable monovalent alicyclic organic groups include, for example, cyclohexyl and cyclooctyl.

[0041] As used herein, the term "aromatic organic group" refers to a carbonyl group, each group containing one or more aromatic rings, which may optionally be substituted with one or more alkyl groups on the aromatic rings, each alkyl group preferably containing 2 to 6 carbon atoms, a halogen group or other functional group, and in the case of a monovalent aromatic group containing two or more rings, it may be a fused ring. Suitable monovalent aromatic groups include, for example, phenyl, tolyl, 2,4,6-trimethylphenyl, 1,2-isopropylmethylphenyl, 1-cyclopentadienyl, naphthyl, anthraceneyl. As used herein, the term "aralkyl" refers to an alkyl, preferably (C2-C6)alkyl, aromatic derivative, wherein the alkyl portion of the aromatic derivative may optionally be interrupted by an oxygen atom, for example phenethyl, phenylpropyl, 2-(1-naphthyl)ethyl, preferably phenylpropyl, phenoxypropyl, biphenoxypropyl.

[0042] "Imine" refers to a compound or group having at least one C(O)-NC(O) functional group. Imines include, but are not limited to, monoimides, diimides, substituted imides, or unsubstituted imides. Imine compounds or groups can be cyclic or acyclic.

[0043] Numerical values ​​given for one or more ranges of a component can be combined to form new or unspecified ranges.

[0044] Imide-functional organopolysiloxane materials are provided. The imide-functional organopolysiloxanes comprise siloxanes modified with imide functional groups. In a further embodiment, the imide-functional organopolysiloxanes may also contain epoxy functional groups. The imide functional groups may be side-attached to siloxane units, or the imide groups may be disposed in the main chain of the material (to effectively connect two or more siloxane units).

[0045] This technology provides imide-functionalized organopolysiloxane materials. In one embodiment, the imide-functionalized organopolysiloxane material is a compound having the structural formula (I):

[0046]

[0047] (I)

[0048] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 and R 14 Each group is independently selected from hydrogen, C1-C15 alkyl, epoxy, C6-C30 aromatic groups, and imide groups, provided that (i) R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from an imide group, and (ii) R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from epoxy groups;

[0049] A1, A2, A3 and L1, L2, L3, L4, L5, L6, L7, L8, L9, L 10 L 11 and L 12Each of these is a linking group independently selected from divalent alkyl, divalent alkenyl, or divalent ether groups.

[0050] o≥1;

[0051] w, x, y and z are each ≥ 0, where (w+x+y+z) ranges from 1 to 60;

[0052] k1, k2, k3, k4, k5, k6, k7, k8, k9, k10, k11, and k12 are each independently ≥ 0; and

[0053] a1, a2, and a3 are each independently ≥ 0.

[0054] The C1-C15 alkyl groups may be selected from straight-chain or branched groups. In one embodiment, the C1-C15 alkyl groups are selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, and isooctyl.

[0055] C6-C30 aromatic groups can be selected from aryl, aralkyl, and alkylaryl. The term "aryl" refers to any monovalent aromatic hydrocarbon group; the term "aralkyl" refers to any alkyl group (as defined herein) in which one or more hydrogen atoms are replaced by the same number of the same and / or different aryl groups (as defined herein); and the term "arylalkyl" refers to any aryl group (as defined herein) in which one or more hydrogen atoms are replaced by the same number of the same and / or different alkyl groups (as defined herein). An aromatic group may contain one or more aromatic rings. In groups having multiple aromatic rings, the rings may be linked by bonds, by linking groups (e.g., divalent hydrocarbon groups or groups having heteroatoms), or may be a fused ring system. An aromatic group may be an array of atoms having at least one monovalent valence and at least one aromatic group. This can include heteroatoms such as nitrogen, sulfur, selenium, silicon, and oxygen, or may consist only of carbon and hydrogen. Suitable aromatic groups may include phenyl, pyridyl, furanyl, thiophene, naphthyl, phenylene, and biphenyl. Aromatic groups can be cyclic structures with 4n+2 "delocalized" electrons, where "n" can be an integer equal to 1 or greater, such as phenyl (n=1), thiophene (n=1), furanyl (n=1), naphthyl (n=2), azulel (n=2), anthracene (n=3), etc. Aromatic groups can also include non-aromatic components. For example, benzyl can be an aromatic group, which can include a benzene ring (aromatic group) and a methylene group (non-aromatic component). Aromatic groups can include one or more functional groups, such as alkyl, alkenyl, alkynyl, haloalkyl, haloaromatic, conjugated dienyl, alcohol, ether, aldehyde, ketone, carboxylic acid, acyl (e.g., carboxylic acid derivatives, such as esters and amides), amino, nitro, etc. Examples of C6-C30 aromatic groups include, but are not limited to, phenyl, naphthyl; o-tolyl, m-tolyl and p-tolyl, xylyl, ethylphenyl and benzyl.

[0056] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from imide, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from epoxy groups, and R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of the groups is selected from C6-C30 aromatic groups. In this embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 The residues are each independently selected from C1-C15 alkyl groups.

[0057] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and R 12 R13 is selected independently from hydrogen, C1-C15 alkyl and C6-C30 aromatic groups, R14 is selected from an imide functional group and R15 is selected from an epoxy functional group.

[0058] In one implementation, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 Each is independently selected from hydrogen and C1-C15 alkyl groups, and R13 and R14 are selected from substituted or unsubstituted diimides.

[0059] The epoxy group is not particularly limited and can be selected according to the needs of a specific purpose or intended application. In one embodiment, the epoxy group is selected from glycidyl or glycidyl ether groups. The epoxy group may have formula (II) or (III):

[0060] (II)

[0061] (III)

[0062] Where R 15 R 16 and R 17 Each is independently selected from C1-C10 divalent hydrocarbon groups.

[0063] The imide group can be selected from groups containing an imide functional group. In the examples, the imide functional group is selected from groups of formulas (IV), (V), and (VI):

[0064] (IV);

[0065] (V);

[0066] (VI)

[0067] Where R 18 R 19 R 20 and R 21 Independently selected from C2 to C30 divalent organic groups, and R 22 It is selected from bonds, C1-C30 divalent organic groups or O atoms. The C2 to C30 divalent groups can be saturated, unsaturated, straight-chain, branched, cyclic, aromatic, etc., and can be unsubstituted or substituted.

[0068] In one implementation, R 18 R 20 and R 21 Each is independently selected from C2 to C30 bivalent chains to form a single ring. In one embodiment, R 18 R 20 and R 21 Independently selected from C2 to C6 bivalent chains. In one implementation, R 18 R 20 and R 21 The group is independently selected from C2 or C3 divalent groups to provide a five- or six-membered imide ring.

[0069] In one implementation, R 19 It is a hydrocarbon containing C5-C30 rings. In one embodiment, the cyclic hydrocarbon can be an unsaturated ring, a saturated ring, a saturated or unsaturated fused ring system, or a polycyclic system separated by bonds or other connecting groups. In another embodiment, the ring can be an aromatic ring.

[0070] In one implementation, R 18 R 20 and R 21 Each is independently selected from C5-C30 cyclic hydrocarbons. In one embodiment, the cyclic hydrocarbon may be an unsaturated ring, a saturated ring, a saturated or unsaturated fused ring system, or a polycyclic system separated by bonds or other connecting groups. In another embodiment, the ring may be an aromatic ring.

[0071] Some non-restrictive examples of R18 include:

[0072]

[0073]

[0074] Unrestricted examples of R19 include:

[0075]

[0076]

[0077] Non-restrictive examples of R20 and R21 include:

[0078]

[0079]

[0080] R 22 The organophosphate group is selected from bonds, C1 to C30 divalent organic groups, or O atoms. The divalent organic group can be straight-chain, branched, or contain one or more cyclic groups, including, for example, C6 to C30 aromatic groups. The C1 to C30 divalent organic group can be unsubstituted or substituted. Substituted organic groups may include, for example, one or more heteroatoms selected from N, O, S, and / or halogen groups (e.g., F). In one embodiment, R... 22 Selected from divalent C1-C10 groups. In one embodiment, R 22 Selected from -CH2-, -CH2CH2-, or -CH2CH2CH2-. In one embodiment, R 22 Selected from ---O--- key (linkage). In one implementation, R 22 Selected from C1-C10 groups that optionally contain at least one COC bond. In one embodiment, R 22 Selected from divalent C1-C10 groups, wherein one or more hydrogen atoms are replaced by fluorine atoms. In one embodiment, R 22 Selected from –(CF2)n-, where n is 1 to 10. In one embodiment, R 22 Selected from (-C(CF3)(CF3)-)m, where m is from 1 to 10.

[0081] Some examples of suitable imide groups include, but are not limited to:

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] Where R 23 and R 24 It can be selected from hydrogen, C1-C15 alkyl, epoxy, C4-C20 cyclic groups, and C6-C30 aromatic groups, which can be substituted or unsubstituted, and wherein the carbon atom in the cyclic or aromatic group can be replaced by a heteroatom selected from O, N or S. b is an integer from 0 to 4. R 23’ It is a divalent organic group containing epoxypropoxy and imide substituents, and R 23’’ It is an amino-terminated siloxane.

[0095] In one implementation, R 1 To R 12 Independently selected from hydrogen, epoxy group, C1-C15 alkyl group, C6-C30 aryl group and imide group, and R 13 and R 14 Selected from C1-C15 alkyl groups, wherein R 1 To R 12 At least one of them is selected from imides, and R 1 To R 12 At least one of them is selected from epoxy groups. In one embodiment, R 1 R 2 R 3 R4 R 5 R 7 R 9 R 10 R 11 and R 12 Independently selected from hydrogen, C1-C15 alkyl groups and C6-C30 aromatic groups, R 6 Selected from imide functional groups, and R 8 Selected from epoxy functional groups. In one exemplary embodiment, the imide-functionalized organopolysiloxane contains an imide functional group, an epoxy functional group, and an alkenyl aryl group at the side-mounted position, as shown in structure A:

[0096]

[0097] Structure A

[0098] In one implementation, R1 to R 12 Independently selected from hydrogen or C1-C15 alkyl, and R 13 and R 14 The groups are independently selected from those containing imide. In one exemplary embodiment, the imide-functionalized organopolysiloxane is a linear molecule comprising an imide functional group linked to a siloxane backbone having a terminal epoxy functional group, as shown in structure B:

[0099]

[0100] Structure B

[0101] In one exemplary embodiment, the imide-functionalized organopolysiloxane comprises a triazine-substituted bisimide functional group, as shown in structure C:

[0102]

[0103] Structure C

[0104] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a diphenyl ether-substituted bisimide functional group, wherein R 19 It is a benzene ring, as shown in structure D:

[0105]

[0106] Structure D

[0107] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a diphenyl ether-substituted bisimide functional group, wherein R 19 It is a polycyclic system, such as biphenyl, as shown in structure E:

[0108]

[0109] Structure E

[0110] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a plurality of imides and substituted diimide functional groups, wherein R 14 It is a diimide-substituted organopolysiloxane (structure (I)), and R 13 It is an imide-substituted organopolysiloxane (structure (I)), and R 14 and R 13 The ethylene linkers (A1 and A2) are attached to the siloxane backbone, as shown in structure F:

[0111]

[0112] Structure F

[0113] In another exemplary embodiment, the imide-functional organopolysiloxane comprises a siloxane backbone having two linking groups at both ends, including a substituted divalent alkyl group, such as an aminoalkyl linking group (A1), at one end, and a -CH(OH)-CH2-O-CH2-substituted aminoalkyl linking group (A2) at the other end, wherein R 13 It is a substituted imide, wherein the substituted imide contains R 23’ It is a divalent organic group containing epoxypropoxy and imide substituents, and the substituted imide also contains R. 23’’ It is an amino-terminated siloxane, as shown in structure G:

[0114]

[0115] Structure G

[0116] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a plurality of imides and substituted diimide functional groups, wherein R 14 R13 is a diimide-substituted organopolysiloxane (structure (I)), and R13 is an imide-substituted organopolysiloxane (structure (I)). 14 and R 13 The ethylene linkers (A1 and A2) are attached to the siloxane backbone, as shown in structure H:

[0117]

[0118] Structure H

[0119] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a plurality of imides and substituted diimide functional groups, wherein R 14It is a diimide-substituted organopolysiloxane (structure (I)), and R 13 It is an imide-substituted organopolysiloxane (structure (I)), and R 14 and R 13 Attached to the siloxane backbone via ethylene linkers (A1 and A2), and R 22 It is -C(CF3)2, as shown in structure J:

[0120]

[0121] Structure J

[0122] In another exemplary embodiment, the imide-functionalized organopolysiloxane comprises a plurality of imide and triazine-substituted diimide functional groups, wherein R 14 R13 is a triazine-substituted diimide (structure (I)), and R13 is an imide-substituted organopolysiloxane (structure (I)), and R 14 and R 13 Attached to the siloxane backbone via ethylene linkers (A1 and A2), and R 22 It is -C(CF3)2, as shown in structure K:

[0123]

[0124] Structure K

[0125] Structure AK illustrates an example of an embodiment of an imide-functionalized organopolysiloxane according to aspects of the present technology as described above.

[0126] In one embodiment, the compound according to the present technology can be prepared by introducing an imide group and an epoxy group into a siloxane unit via a hydrosilylation reaction. In one embodiment, an alkenyl-functionalized imide reacts with a hydride-functionalized siloxane to provide an imide-functionalized siloxane. The reaction can be controlled such that a molar excess of the hydride functional group is present after the reaction with the imide, such that the imide-functionalized siloxane comprises the hydride functional group. The imide-functionalized siloxane comprising the hydride functional group is then reacted with an alkenyl-functionalized epoxy group to produce an imide-functionalized organopolysiloxane.

[0127] The reaction can be carried out in a solvent. A solvent may be required, for example, to dissolve the alkenyl-functionalized imide. The reaction can also be carried out at elevated temperatures. In embodiments, the reaction for adding the imide and the epoxy group can be carried out at temperatures of about 50°C to about 110°C, about 60°C to about 100°C, or about 75°C to about 90°C.

[0128] Alkenyl-functionalized imides can be selected, for example, from compounds of the following formula:

[0129] ;

[0130] ; and / or

[0131]

[0132] Where R 18 R 19 R 20 R 21 and R 22 As described above, and R' is independently selected from C2-C30 alkenyl functional groups. Generally, alkenyl functional groups include terminal alkenyl groups. In the examples, R' is selected from vinyl, allyl, methyl allyl, butenyl, isobutenyl, sec-butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, or decenyl functional groups and branched groups with 6 or more carbon atoms.

[0133] Hydrosilylation catalysts are used in each reaction. The catalysts used in the reactions of alkenyl-functionalized imides can also be used in the reactions of alkenyl-functionalized epoxy groups with imide-functionalized siloxanes. There are no particular limitations on the hydrosilylation catalysts, and any suitable hydrosilylation catalyst can be used in the reaction. In one embodiment, the catalyst is selected from platinum group metal-based hydrosilylation catalysts. For the purposes of this invention, the term "platinum group metals" means ruthenium, rhodium, palladium, osmium, iridium, and platinum. In one embodiment, the hydrosilylation catalyst is platinum-based. A further preferred hydrosilylation catalyst is a platinum-alkenylsiloxane complex. Particularly preferred are hydrosilylation catalysts selected from platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complexes (Karstedt complexes), platinum-1,3-diallyl-1,1,3,3-tetramethyl-disiloxane complexes, platinum-1,3-divinyl-1,3-dimethyl-1,3-diphenyldisiloxane complexes, platinum-1,1,3,3-tetraphenyldisiloxane complexes, and platinum-1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane complexes. More preferably, the hydrosilylation catalyst is platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complexes (Karstedt complexes).

[0134] In an alternative embodiment, the alkenyl-functionalized siloxane can be used with a hydride-functionalized imide to provide an imide-functionalized siloxane. The reaction can be controlled such that a molar excess of alkenyl functional group is present after the reaction with the imide, such that the imide-functionalized siloxane comprises the alkenyl functional group. The imide-functionalized siloxane comprising the alkenyl functional group is then reacted with a hydride-functionalized epoxide to produce an imide-functionalized organopolysiloxane.

[0135] In another embodiment, the imide-functionalized organopolysiloxane according to the present technology can be prepared by an imidization reaction. The imidization reaction involves adding a dianhydride substituted with an aliphatic or aromatic group; a diamino or dianhydride-functionalized siloxane; and an aliphatic or aromatic-functionalized amine to produce an imide-functionalized siloxane comprising one or more substituents. The imidization reaction involves reacting a diaminosiloxane with a dianhydride and optionally a functionalized amino organic group and / or anhydride and heating the mixture. This reaction can be carried out as a "one-pot" reaction. In embodiments, the reaction can be carried out at temperatures of approximately 100°C to approximately 200°C, approximately 120°C to approximately 180°C, approximately 130°C to approximately 170°C, or approximately 150°C to approximately 160°C.

[0136] Diaminosiloxanes are siloxanes with the desired chain length having a terminal amino group.

[0137] A dianhydride can be selected to provide an imide with the desired structure. In embodiments, the dianhydride is selected from compounds of the following formula:

[0138]

[0139]

[0140] Where R 19 R 20 R 21 and R 22 As stated above.

[0141] Functional amines may contain organic groups, including but not limited to aliphatic, cyclic, acyclic, alicyclic, heterocyclic, aromatic, and heteroaromatic groups. In some embodiments, functional amines include, but are not limited to, monoamines, diamines, and triamines. In such embodiments, each of these amines may be a primary, secondary, or tertiary amine.

[0142] The imidization reaction can optionally use anhydride-terminated siloxanes, wherein the anhydride-terminated siloxanes are obtained by hydrosilylation of an alkenyl-functionalized anhydride with a hydride-functionalized siloxane. The alkenyl-functionalized anhydride can have the following formula:

[0143]

[0144] Where R 18 As mentioned above, and R 25 It is an alkenyl functional group. The alkenyl functional group can be selected from C2-C30 alkenyl functional groups. R 25 Examples include, but are not limited to, vinyl, allyl, methylallyl, butenyl, isobutenyl, sec-butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, or decenyl functional groups and branched groups with six or more carbon atoms.

[0145] Imide-functionalized organopolysiloxanes can be used to form composite materials. Composite materials containing imide-functionalized organopolysiloxanes have properties such as thermal stability, high curability, and / or low thermal expansion. In one embodiment, the composite material comprises an imide-functionalized organopolysiloxane, a functional polymer / resin capable of reacting with the imide-functionalized organopolysiloxane, a catalyst, and optional additives, such as, but not limited to, fillers, plasticizers, etc.

[0146] Examples of suitable polymers capable of reacting with imide-functional organopolysiloxanes include, but are not limited to, reactive polymers, including but not limited to: olefinically unsaturated monomers and prepolymers, vinyl-functional monomers and prepolymers, hydride-functional monomers and prepolymers, hydroxyl-functional monomers and prepolymers, epoxy-functional monomers and prepolymers, amino-functional monomers and prepolymers, (meth)acrylic acid and its ester derivatives, polyurethanes, polyethers, polyesters, polylactones, polylactide, polyglycolic acid, polyamides, polyethylene, polypropylene, poly(epoxides) such as polyethylene oxide, polypropylene oxide, polybutadiene, polybutene, polyacrylonitrile, polyvinyl chloride, polystyrene, polysulfone, PEEK, polycarbonate, polyepoxides, fluoropolymers such as PTFE, polydifluoroethylene, synthetic and natural rubbers, phenolic formaldehyde, melamine formaldehyde, and urea formaldehyde. Polymers of natural or semi-synthetic origin, such as polysaccharides, cellulose, proteins, polypeptides, poly(amino acids), organosilicon polymers, such as, but not limited to, polysiloxanes, polysilicates, polysilsesquioxanes, polysilanes, ionic modified forms of the above substances, and various isomers and copolymers of the above polymers.

[0147] The present technology has been described in the foregoing detailed description and with reference to various aspects and embodiments. The present technology can be further understood with reference to the following embodiments. These embodiments are intended to further illustrate aspects and implementations of the present technology, and are not necessarily limited to these aspects or implementations.

[0148] Example

[0149] Example 1: Synthesis of organopolysiloxanes with side groups, structure A, having an average chemical formula where w=44, x=1, y=5, and z=5. (1) Side-attached hydride siloxane MD 44 D' 11M (150 g), 2-allyl isoindoline-1,3-dione (7.4 g), and toluene (150 mL) were placed in a three-necked round-bottom flask of appropriate size equipped with a thermopocket, condenser, and dropping funnel. The temperature of the reaction mixture was raised to 93 °C, and then 10 ppm of platinum catalyst was added to the reaction mixture. (2) After step 1 was completed, α-methylstyrene (25.69 g) was placed in the dropping funnel and added dropwise to the reaction mixture. After the α-methylstyrene was completely added and the reaction mixture was exothermically stabilized, the internal temperature of the reaction mixture was raised to 96.5 °C. (3) After step 2 was completed, allyl glycidyl ether (33.9 g) was placed in the dropping funnel and added dropwise to the reaction mixture. After the reaction was completed, the mixture was carbonized to remove colloidal Pt while stirring at 50 °C for 4 hours. The treated material was filtered and separated from the carbon by using a sintering funnel with a diatomaceous earth bed, and the filtrate was collected. The solvent was then removed from the filtrate to obtain the product, a yellow, viscous product, as shown in structure A. The product's M was confirmed by gel permeation chromatography (GPC). w 12714 gmol -1 The polydispersity index (PDI) is 2.1.

[0150] Example 2: Synthesis of an organopolysiloxane with side groups, structure A, having an average chemical formula where w=11, x=0.5, y=1.8, and z=1.7. (1) Side-attached hydride siloxane MD 11 D'4M (150 g), 2-allyl isoindoline-1,3-dione (8.52 g), and toluene (50 mL) were placed in a three-necked round-bottom flask of appropriate size equipped with a thermometer, condenser, and dropping funnel. The temperature of the reaction mixture was raised to 90 °C, and then 10 ppm of platinum catalyst was added to the reaction mixture. (2) After step 1 was completed, α-methylstyrene (28.77 g) was placed in a dropping funnel and added dropwise to the reaction mixture. After the α-methylstyrene was completely added, the temperature of the reaction mixture was raised to 95 °C. (3) After step 2 was completed, allyl glycidyl ether (37.91 g) was placed in a dropping funnel and added dropwise to the reaction mixture. After the reaction was completed, the mixture was carbonized to remove colloidal Pt while stirring the mixture at 50 °C for 4 hours. The treated material was filtered and separated from the carbon using a sintering funnel with a diatomaceous earth bed, and the filtrate was collected. The solvent was then removed from the filtrate to obtain a yellow, viscous product, as shown in structure A. GPC confirmed the M-type of the product. w 4823 gmol -1 The PDI is 2.5.

[0151] Example 3: Synthesis of organopolysiloxane, structure B. N,N-diallylpyromellitic diaimide (20 g) was placed in a round-bottom flask equipped with a thermometer, condenser, and dropping funnel. Toluene was added to dissolve the diaimide. The mixture was then heated to 75°C, followed by the addition of telechelic hydride siloxane M'D. 12 M' (150 g) was added to a round-bottom flask (RBF). Then, 10 ppm of platinum catalyst was added to the reaction mixture, and exothermic reaction was observed during the addition of the hydride. After stirring the mixture for 2 hours, proton NMR was recorded. Following the consumption of N,N-diallylpyromellitic diimide, the imide-modified siloxane hydride was further capped with allyl glycidyl ether (25 g). The reaction mixture was stirred thoroughly at 75 °C. Proton NMR was then recorded to verify complete hydride consumption. After the reaction was complete, the mixture was carbonized to remove colloidal Pt while stirring at 50 °C for 4 hours. The treated material was filtered and separated from the carbon using a sintering funnel with a diatomaceous earth bed, and the filtrate was collected. The solvent was then removed from the filtrate to give a pale yellow viscous substance, as shown in structure B. The M of the product was confirmed by GPC. w 5798 gmol -1 The PDI is 1.9.

[0152] Example 4: Synthesis of organopolysiloxane, structure B. N,N-diallylpyromellitic diaimide (51.82 g) was placed in a round-bottom flask equipped with a thermometer, condenser, and dropping funnel. Toluene was added to dissolve the diaimide. The mixture was then heated to 75°C, and then 200 g of the telechelic hydride siloxane M'D9M' was added to the round-bottom flask. 10 ppm of platinum catalyst was then added to the reaction mixture, and exothermic reaction was observed during the addition of the hydride. After stirring the mixture for 2 hours, proton NMR was recorded. After the N,N-diallylpyromellitic diaimide was consumed, the diaimide-modified siloxane hydride was further capped with allyl glycidyl ether (18 g). The reaction mixture was stirred completely at 75°C. Proton NMR was then recorded to verify complete hydride consumption. After the reaction was complete, the mixture was charcoal-treated to remove colloidal Pt while being stirred at 50°C for 4 hours. The treated material was filtered and separated from the charcoal using a sintered funnel with a diatomaceous earth bed, and the filtrate was collected. The solvent was then removed from the filtrate to obtain a light yellow viscous substance, as shown in structure B. The M of the product was confirmed by GPC. w 8802 gmol -1 The PDI is 2.9.

[0153] Example 5: Synthesis of organopolysiloxane, structure D, amino-terminated siloxane NH2MD10 MNH2 (174 g), 4,4'-diaminodiphenyl ether (15 g), and pyromellitic dianhydride (66 g) were placed in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (476 g) and γ-butyrolactone (119 g) were added to dissolve them. Then, pyridine (0.8 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, a mixture of methanol (680 g) and water (170 g) was added. A brown powder precipitated and filtered to give an organopolysiloxane product as shown in structure D. The M of the product was determined by GPC. w 8650 gmol -1 The PDI was 2.46, and the imidization rate was determined to be 50% by calculating the peak Abs using FT-IR. (Abs. 1720 cm⁻¹) -1 / (Abs.1720cm -1 +Abs.3300cm -1 )).

[0154] Example 6: Synthesis of organopolysiloxane, structure E, amino-terminated siloxane NH2MD 10 MNH2 (191 g), 4,4′-diaminodiphenyl ether (7 g), and 4,4′-biphthalic anhydride (83 g) were placed in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (526 g) and γ-butyrolactone (131 g) were added to dissolve them. Then, triethylamine (1.1 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, methanol (1881 g) was added. A brown viscous liquid separated at the bottom of the round-bottom flask, and the supernatant was removed. The residual solvent in the brown viscous liquid was removed by vacuum to obtain the product, namely the organopolysiloxane with structure E. The M of the product was confirmed by GPC. w 6050 gmol -1 The PDI was 1.97, and the imidization rate was confirmed to be 60% by calculating the peak Abs using FT-IR. (Abs. 1720 cm⁻¹) -1 / (Abs.1720cm -1 +Abs.3300cm -1 )).

[0155] Example 7: Synthesis of organopolysiloxanes, structure F, amino-terminated siloxane NH2MD 10 Siloxanes capped with MNH2 (174 g), 4,4′-biphthalic anhydride (47 g), and allyl 3-propyl succinic anhydride ASA MD 10 M ASA The synthesis of (71 g) was carried out in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (545 g) and γ-butyrolactone (136 g) were added to dissolve them. Then imidazole (0.7 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, a mixture of methanol (779 g) and water (194 g) was added. A brown viscous liquid separated from the bottom of the round-bottom flask, and the supernatant was removed. The residual solvent in the brown viscous liquid was removed by vacuum to give the product, namely the organopolysiloxane shown in structure F. The Mw of the product was confirmed to be 5000 gmol by GPC. -1 The PDI was 1.64, and the imidization rate was confirmed to be 80% by calculating the peak Abs using FT-IR. (Abs. 1720 cm⁻¹) -1 / (Abs.1720cm -1 +Abs.3300cm -1 )).

[0156] Example 8: Synthesis of organopolysiloxanes, structure H, amino-terminated siloxane NH2MD 10 Siloxanes capped with MNH2 (174 g), 4,4′-biphthalic anhydride (35 g), and allyl 3-propyl succinic anhydride ASA MD 10 M ASA The synthesis of (59 g) was carried out in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (519 g) and γ-butyrolactone (130 g) were added to dissolve them. Then imidazole (0.7 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. The reaction mixture was cooled to 25 °C and maleic anhydride (10 g) was added. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, a mixture of methanol (741 g) and water (185 g) was added. A brown viscous liquid separated at the bottom of the round-bottom flask, and the supernatant was removed. The residual solvent in the brown viscous liquid was removed by vacuum to give the product, namely the organopolysiloxane with structure H. The M of the product was confirmed by GPC. w 4800 gmol -1 The PDI was 1.71, and the imidization rate was confirmed to be 80% by FT-IR.

[0157] Example 9: Synthesis of organopolysiloxane, structure J, by amino-terminated siloxane NH2MD 10 MNH2 (174 g), 4,4′-(hexafluoroisopropylidene) phthalic anhydride (91 g), and allyl 3-propyl succinic anhydride-terminated siloxane ASA MD 10 M ASA (18 g) was placed in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (528 g) and γ-butyrolactone (132 g) were added to dissolve them. Then imidazole (0.7 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, a mixture of methanol (755 g) and water (189 g) was added. A brown viscous liquid separated at the bottom of the round-bottom flask, and the supernatant was removed. The residual solvent in the brown viscous liquid was removed by vacuum to obtain the product, namely the organopolysiloxane with structure J. The M of the product was confirmed by GPC. w 6250 gmol -1 The PDI was 2.1, and the imidization rate was confirmed to be 90% by FT-IR.

[0158] Example 10: Synthesis of organopolysiloxane, structure K, amino-terminated siloxane NH2MD 10 MNH2 (174 g), melamine monomer (4 g), 4,4'-(hexafluoroisopropylidene) phthalic anhydride (99 g), and allyl 3-propyl succinic anhydride-terminated siloxane ASA MD 10 M ASA (49 g) was placed in a round-bottom flask equipped with a thermometer and a condenser. Dimethylacetamide (608 g) and γ-butyrolactone (152 g) were added to dissolve them. Then imidazole (0.7 g) was added to the mixture. The mixture was heated to 160 °C and stirred at 160 °C for 3 hours. After cooling the mixture to 25 °C, a mixture of methanol (815 g) and water (272 g) was added. A yellow viscous liquid separated at the bottom of the round-bottom flask, and the supernatant was removed. The residual solvent in the yellow viscous liquid was removed by vacuum to obtain the product, namely the organopolysiloxane with structure K. The M of the product was confirmed by GPC. w 5500 gmol -1 The PDI was 2.1, and the imidization rate was confirmed to be 90% by FT-IR.

[0159] The foregoing description includes examples from this specification. Of course, for the purposes of describing this specification, it is impossible to describe all conceivable combinations of components or methods, but those skilled in the art will recognize that many further other combinations and arrangements are possible. Therefore, this specification is intended to cover all such substitutions, modifications, and variations, provided they fall within the spirit and scope of the appended claims. Furthermore, with respect to the use of the term "comprising" in the detailed description or claims, such a term is intended to be inclusive, and is used in a manner similar to the term "including," since "including" is interpreted as inclusive when used as a transitional word in a claim.

[0160] The siloxanes of the present invention, containing imide, epoxy, aliphatic, and aromatic groups, have been found to possess excellent properties such as thermal stability and low thermal expansion when used in composite formulations. Furthermore, the siloxanes of the present invention allow us to prepare compositions with low moisture retention and produce cured articles with high mechanical strength.

[0161] The foregoing description identifies various non-limiting embodiments of organopolysiloxanes. Modifications can be made by those skilled in the art, as well as those who can manufacture and use the invention. The disclosed embodiments are for illustrative purposes only and are not intended to limit the scope of the invention or the subject matter set forth in the claims.

Claims

1. A siloxane comprising an imide functional group and at least one functional group selected from epoxy, hydride, aromatic, aliphatic, amine and / or acryloyl or acryloyloxy, wherein the siloxane is selected from linear siloxanes and nonlinear siloxanes, wherein the nonlinear siloxane comprises at least two of the functional groups selected from epoxy, hydride, aromatic, aliphatic, amine and / or acryloyl or acryloyloxy.

2. The siloxane according to claim 1, wherein the siloxane is based on formula (I). Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 and R 14 Each is independently selected from hydrogen, C1-C15 alkyl, epoxy, C6-C30 aromatic groups and imide groups, provided that (i)R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from an imide group, and (ii)R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 and R 14 At least one of them is selected from epoxy groups; A1, A2, A3 and L1, L2, L3, L4, L5, L6, L7, L8, L9, L 10 L 11 and L 12 Each of these is a linking group independently selected from divalent alkyl, divalent alkenyl, and divalent ether groups; o≥1； w, x, y and z are each ≥ 0, where (w+x+y+z) ranges from 1 to 60; k1, k2, k3, k4, k5, k6, k7, k8, k9, k10, k11, and k12 are each independently ≥ 0; and a1, a2, and a3 are each independently ≥ 0.

3. The siloxane according to claim 2, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from imide, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from epoxy groups, and R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 At least one of them is selected from C6-C30 aromatic groups.

4. The siloxane according to claim 2, wherein R1, R2, R3, R4, R5, R7, R9, R 10 R 11 and R 12 Independently selected from hydrogen, C1-C15 alkyl groups and C6-C30 aromatic groups, R 13 Selected from imide functional groups, and R 14 Selected from epoxy functional groups.

5. The siloxane according to claim 2, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and / or R 12 Each is independently selected from hydrogen and C1-C15 alkyl groups, and R 13 and R 14 Selected from substituted or unsubstituted diimides.

6. The siloxane according to any one of claims 2-5, wherein the imide group is selected from groups of formula (IV), (V) and (VI): (IV); (V)； (WE) R 18 R 19 R 20 and R 21 Independently selected from C2 to C30 divalent organic groups, and R 22 Selected from bonds, C1-C30 divalent organic groups, or O atoms.

7. A method for forming an imide-functional organopolysiloxane, comprising: (i) reacting an alkenyl-functionalized imide with a hydride-functionalized siloxane to produce an imide-functionalized siloxane, wherein the imide-functionalized siloxane contains an unreacted hydride group, and (ii) Reacting an imide-functionalized siloxane having an unreacted hydride group with an alkenyl-functionalized epoxy group to provide an imide-functionalized organopolysiloxane comprising an imide and an epoxy functional group.

8. The method of claim 7, further comprising (iii) reacting an imide-functionalized siloxane having an unreacted hydride group with an alkenyl-functionalized aromatic group and / or aliphatic group to provide an imide-functionalized organopolysiloxane comprising an imide and an aromatic or aliphatic substituent.

9. The method according to claim 7, wherein step (ii) is after step (i).

10. The method according to claim 8, wherein step (iii) follows step (i), and step (ii) follows step (iii), wherein the imide-functionalized organopolysiloxane having unreacted hydride groups comprising imide and aromatic and / or aliphatic substituents reacts with alkenyl-functionalized epoxy groups to provide an imide-functionalized organopolysiloxane comprising imide, aromatic and / or aliphatic substituents, and epoxy functional groups.

11. The method of claim 7, wherein the imide group and the epoxy group are introduced into the main chain or side position of the imide-functional organopolysiloxane.

12. The method of claim 10, wherein the imide group, the epoxy group, and the aromatic or aliphatic group are introduced into the main chain or side position of the imide-functional organopolysiloxane.

13. The method according to claim 7, wherein each of the reactions under (i) and (ii) is carried out in the presence of a hydrosilylation catalyst.

14. A method for forming an imide-functional organopolysiloxane, comprising: In a one-pot reaction, an aliphatic or aromatic substituted dianhydride; a diamino or dianhydride-functionalized siloxane; and an aliphatic or aromatic-functionalized amine are added to produce an imide-functionalized organopolysiloxane containing one or more substituents.

15. A composite material comprising an organopolysiloxane with imide functionality according to any one of claims 1-6.

16. The composite material of claim 15, further comprising a functional polymer / resin capable of reacting with an imide-functional organopolysiloxane, and a catalyst.

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