Liquid Imide-Modified Organopolysiloxane Heat Resistance

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Solution Overview

Problem

Current methods for preparing imide-modified organopolysiloxanes result in solid materials, making handling difficult due to the presence of recurring imide structures, and they are not solvent dilutable, limiting their applications.

Innovation Solution

A method involving the reaction of an organopolysiloxane with an organic compound and a Lewis acid catalyst, followed by a silylating agent, to form a liquid organopolysiloxane with an imide structure, which can be cured by photoirradiation without a initiator, allowing for the creation of a one-part resin.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If recurring imide structures are present in the polymer backbone, then heat resistance is improved, but the material becomes solid and handling becomes difficult

Engineering Contradiction:
Improveheat resistanceVSAvoidhandling ease
Core Design Contradiction:
TemperatureVSEase of operation

Solution Approach 1:

The patent segments the imide structure from the polymer backbone by placing it only on side chains rather than in the backbone itself. This is achieved by reacting amino group-containing organopolysiloxane with carboxylic acid anhydride to form imide groups as side chain modifications, while the backbone remains composed of flexible siloxane bonds. This segmentation allows the material to maintain heat resistance from the imide groups while preserving liquid state and handling ease through the flexible backbone.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent applies local quality by concentrating the rigid imide structures locally on side chains rather than distributing them throughout the backbone. The side chains serve as localized regions with high thermal stability, while the backbone maintains its flexibility and liquid properties. This localized placement of functional groups achieves heat resistance without sacrificing handling characteristics.

Inventive Principle:
Principle #3Local quality

2Temperature

If recurring imide structures are present in the polymer backbone, then heat resistance is improved, but the material becomes non-dilutable and application versatility is reduced

Engineering Contradiction:
Improveheat resistanceVSAvoidsolvent dilutability
Core Design Contradiction:
TemperatureVSAdaptability or versatility

Solution Approach 1:

By segmenting the imide structure to side chains only, the patent preserves the solvent dilutability of the polysiloxane backbone. The backbone maintains its characteristic flexibility and compatibility with various solvents, while the side chains provide localized heat resistance. This allows the material to be diluted with solvents for application and then cured, expanding versatility.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates a composite structure combining the flexible, solvent-compatible siloxane backbone with thermally stable imide side chains. This composite architecture integrates the beneficial properties of both components: the backbone provides processability and dilutability, while the side chains contribute heat resistance, achieving both versatility and thermal performance.

Inventive Principle:
Principle #40Composite materials

3Reliability

If a two-part system with photoinitiator is used, then photocuring capability is achieved, but device complexity and ease of operation are reduced

Engineering Contradiction:
Improvephotocuring capabilityVSAvoidsystem complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent incorporates photopolymerizable functional groups directly into the organopolysiloxane structure, allowing the material to self-cure upon light exposure without requiring external photoinitiators. The imide-modified polysiloxane contains built-in photoreactive groups that initiate polymerization automatically when irradiated, eliminating the need for separate initiator components and simplifying the system to a single-component formulation.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent merges the photopolymerization functionality with the main polysiloxane structure by incorporating photoreactive groups into the molecular structure. This combines the resin and initiator functions into a single material, allowing photocuring to proceed without adding separate components. The merging of functions reduces system complexity while maintaining reliable photocuring capability.

Inventive Principle:
Principle #5Merging (Combining)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The method produces a liquid organopolysiloxane with excellent heat resistance that can be cured by light exposure without a photoinitiator, enabling its use in various applications such as coating materials and rubber materials.

Implementation Method 1

The method involves the reaction of an organopolysiloxane with an organic compound and a Lewis acid catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

followed by a silylating agent, to form a liquid organopolysiloxane with an imide structure

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 3

The maleimide group is a functional group having a carbon-carbon double bond conjugated with the two carbonyl groups of the imide. It has radical polymerizability, along with which it has the singular attribute that the double bond site dimerizes under the effect of light.

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP3421477B1Organopolysiloxane and production method therefor, and curable composition
Publication Date: 2020.12.23 SHIN ETSU CHEMICAL CO LTD
  • EP3421477B1 patent drawing
  • EP3421477B1 patent drawing
  • EP3421477B1 patent drawing

AI summary

Provided are: a novel imide-modified organopolysiloxane in a liquid form having excellent resistance to heat; a method for producing the organopolysiloxane; and a curable composition that contains the organopolysiloxane and that can be cured by irradiation with light without using an initiator. The organopolysiloxane is represented by formula (1). (Wherein: each R1 represents an unsubstituted or substituted monovalent hydrocarbon group having 1-10 carbon atoms or an organic group having a structure represented by formula (2) or (3), and at least one of the R1s is the organic group having a structure represented by formula (2) or (3); a represents an integer of 2 or more; b, c, and d each represent an integer of 0 or more; and 2 ≤ a+b+c+d ≤ 1,000 is satisfied.) (Wherein: R2-R7 each represent a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1-10 carbon atoms; R2 or R3 may be linked with R4 or R5 to form a ring, and R6 may be linked with R7 to form a ring; m and n each represent an integer of 0-3; and X and Y each represent an unsubstituted or substituted divalent hydrocarbon group that has 1-10 carbon atoms and that optionally contains an intervening heteroatom. A dashed line represents a bond.)