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KR-20260066162-A - imide-acting organopolysiloxane

KR20260066162AKR 20260066162 AKR20260066162 AKR 20260066162AKR-20260066162-A

Abstract

An imide-functional organopolysiloxane is disclosed and described herein. The imide-functional organopolysiloxane comprises a plurality of functional groups, and in an embodiment, comprises at least an imide functional group and an epoxy functional group. Additionally, a composite material comprising the imide-functional organopolysiloxane is provided.

Inventors

  • 카우르 반프리트
  • 이지마 요이치로
  • 시바수브라마니안 카르티케얀
  • 사사키 모토시
  • 푸칸 몬지트
  • 후지와라 나오야
  • 모치즈키 쿄헤이

Assignees

  • 모멘티브 퍼포먼스 머티리얼즈 인크.

Dates

Publication Date
20260512
Application Date
20240917
Priority Date
20230919

Claims (16)

  1. A siloxane comprising an imide functional group and at least one functional group selected from epoxy, hydride, aromatic, aliphatic, amine, and/or acrylic or acryloxy, The siloxane is selected from linear siloxane and non-linear siloxane, and the non-linear siloxane comprises at least two of the functional groups selected from epoxy, hydride, aromatic, aliphatic, amine, and/or acrylic or acryloxy.
  2. In claim 1, The above siloxane is a siloxane according to the following formula (I): Here, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11, R12 , R13 , and R14 are each independently selected from hydrogen, C1-C15 alkyl, epoxy groups, C6- C30 aromatic containing groups, and imide groups, provided that (i) at least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11 , R12 , R13 , and R14 is selected from imide groups, and (ii) R1 , R2 , R3 , R4 , R5, R6 , R7 , At least one of R8 , R9 , R10 , R11 , R12 , R13 , and R14 is selected from epoxy groups; A1 , A2 , A3 , and L1 , L2 , L3 , L4, L5 , L6 , L7 , L8 , L9 , L10 , L11 , and L12 are each independently linked groups selected from divalent alkyl groups, divalent alkenyl groups, and divalent ether groups; o is ≥1 and; w, x, y, and z are each ≥0, where (w + x + y + z) is between 1 and 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. In claim 2, At least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11 , and/or R12 is selected from imide, at least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8, R9 , R10 , R11 , and/or R12 is selected from epoxy, and at least one of R1, R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10, R11 , and /or R12 is selected from C6-C30 aromatic groups, siloxane.
  4. In claim 2, R1 , R2 , R3 , R4 , R5 , R7 , R9 , R10 , R11 , and R12 are independently selected from hydrogen, C1-C15 alkyl groups, and C6-C30 aromatics, R13 is selected from imide functional groups, and R14 is selected from epoxy functional groups, siloxane.
  5. In claim 2, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9, R10 , R11 , and/or R12 are each independently selected from hydrogen and C1-C15 alkyl groups, and R13 and R14 are selected from substituted or unsubstituted biimides, siloxane.
  6. In any one of claims 2 to 5, The above imide group is a siloxane selected from the group of the following formulas (IV), (V), and (VI): (IV); (V); (VI) Here, R18 , R19 , R20 , and R21 are independently selected from C2 to C30 divalent organic groups, and R22 is selected from bonds, C1-C30 divalent organic groups, or O atoms.
  7. (i) a step of reacting an alkenyl functional imide with a hydride functional siloxane to produce an imide functional siloxane, wherein the imide functional siloxane contains unreacted hydride groups; and (ii) a step of reacting the above-mentioned imide-functional siloxane having unreacted hydride groups with an alkenyl-functional epoxy to provide an imide-functional organopolysiloxane comprising imide and epoxy functional groups; a method for forming an imide-functional organopolysiloxane comprising
  8. In claim 7, (iii) a step of reacting the above-mentioned imide-functional siloxane having unreacted hydride groups with alkenyl-functional aromatic groups and/or aliphatic groups to provide an imide-functional organopolysiloxane comprising imide and aromatic or aliphatic substitutions, the method further comprising.
  9. In claim 7, The above step (ii) is a method performed following step (i).
  10. In claim 8, A method wherein, following step (i), step (iii) is performed, and then step (ii) is performed, wherein an imide-functional organopolysiloxane having unreacted hydride groups comprising an imide and aromatic and/or aliphatic substitutions reacts with an alkenyl-functional epoxy to provide an imide-functional organopolysiloxane comprising an imide, aromatic and/or aliphatic substitutions, and epoxy functional groups.
  11. In claim 7, A method in which the imide and epoxy groups are introduced into the main chain or pendant position of the imide-functional organopolysiloxane.
  12. In claim 10, A method in which the imide, epoxy, and aromatic or aliphatic groups are introduced into the main chain or pendant position of the imide-functional organopolysiloxane.
  13. In claim 7, A method in which each of the reactions of (i) and (ii) is carried out in the presence of a hydrosilylation catalyst.
  14. A method for forming an imide-functional organopolysiloxane, comprising the step of adding an aliphatic or aromatic substituted dianhydride; a diamino or dianhydride functional siloxane; and an aliphatic or aromatic functional amine to a single-pot reaction to produce an imide-functional organopolysiloxane comprising one or more substituents.
  15. A composite material comprising an imide-functional organopolysiloxane according to any one of claims 1 to 6.
  16. In claim 15, A composite material further comprising a functional polymer/resin capable of reacting with the above-mentioned imide-functional organopolysiloxane, and a catalyst.

Description

imide-acting organopolysiloxane The present invention relates to imide-functional organopolysiloxanes. In particular, the present invention relates to imide-functional organopolysiloxanes modified with imide and/or epoxy functional groups. Silicone materials are used in a wide variety of applications. Silicone materials exhibit various properties that make them suitable for specific applications. For example, they can be used as additives to impart specific characteristics to polymer systems. For instance, silicone materials can provide flexibility, thermal stability, strength, and optical transparency to compositions. However, not all silicone materials achieve the same effects or are suitable for all applications. In particular, it is a challenge to find silicone materials that possess a combination of properties such as high curability, low thermal expansion, and high thermal stability. There is a need for silicone materials that possess this combination of properties. The following is a summary of the present disclosure to provide a basic understanding of some aspects. This summary is not intended to identify essential or important elements, or to define any limitations of the embodiments or claims. Additionally, this summary may provide a simplified overview of some aspects that may be described in more detail in other parts of the present disclosure. An imide-functional organopolysiloxane is provided. The imide-functional organopolysiloxane comprises an imide functional group and an epoxy functional group. In an embodiment, the imide and/or epoxy functional group may be present in the form of a pendant on the siloxane chain. In another embodiment, the imide-functional organopolysiloxane may comprise an imide group connecting the siloxane units. Additionally, a method for preparing the imide-functional organopolysiloxane is provided. In an embodiment, each imide and epoxy functional group is separately introduced into the siloxane through a hydrosilylation reaction with the siloxane. In an embodiment, 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 the imide-functional siloxane. Subsequently, the imide-functional siloxane having the remaining hydride functional group reacts with an alkenyl-functional epoxy compound to provide the imide-functional organopolysiloxane. In a further embodiment, an alkenyl-functional aromatic group or an aliphatic group may also be introduced into the imide-functional organopolysiloxane by hydrosilylation. In another aspect, a method for preparing an imide-functional organopolysiloxane is provided, comprising reacting an aliphatic, aromatic-substituted dianhydric, diamino or dianhydric functional siloxane and an aliphatic or aromatic functional amine in a one-pot reaction. 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 acrylic or acryloxy, wherein the siloxane is selected from linear siloxane and non-linear siloxane, and the non-linear siloxane comprises at least two of the functional groups selected from epoxy, hydride, aromatic, aliphatic, amine, and/or acrylic or acryloxy. In one embodiment, the siloxane is according to the following formula (I): Here, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11, R12 , R13 , and R14 are each independently selected from hydrogen, C1-C15 alkyl, epoxy groups, C6- C30 aromatic containing groups, and imide groups, provided that (i) at least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11 , R12 , R13 , and R14 is selected from imide groups, and (ii) R1 , R2 , R3 , R4 , R5, R6 , R7 , At least one of R8 , R9 , R10 , R11 , R12 , R13 , and R14 is selected from epoxy groups; A1 , A2 , A3 , and L1 , L2 , L3 , L4, L5 , L6 , L7 , L8 , L9 , L10 , L11 , and L12 are each independently linker groups selected from divalent alkyl groups, divalent alkenyl groups, and divalent ether groups; o is ≥1 and; w, x, y, and z are each ≥0, where (w + x + y + z) is 1 to 60; k1, k2, k3, k4, k5, k6, k7, k8, k9, k10, k11, k12 are each independently ≥0; and a1, a2, and a3 are each independently ≥0. In one embodiment, at least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8, R9 , R10 , R11 , and/or R12 is selected from imide, at least one of R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9, R10 , R11 , and/or R12 is selected from epoxy, and at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 , and / or R12 is selected from C6 - C30 aromatic groups. In one embodiment, R1 , R2 , R3 , R4 , R5 , R7 , R9 , R10 , R11 , and R12 are independently selected from hydrogen, C1-C15 alkyl groups, and C6-C30 aromatic groups, R13 is selected from imide functional groups, and R14 is selected from epoxy functional groups. In one embodiment, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 , R9 , R10 , R11 , and/or R12 are each i