Aryl Compound Crosslinked Polymer Heat Resistance

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Solution Overview

Problem

Existing aryl compounds with glycidyl and (meth)allyl groups exhibit poor heat resistance and bond strength due to low molecular weight linking hydrocarbons, leading to inadequate performance in polymer formation and CVD film resistance.

Innovation Solution

An aryl compound with at least three glycidyl and three (meth)allyl groups is synthesized by reacting an aryl compound with (meth)allyl-containing phenol groups and 2-halomethyloxirane, resulting in a polymer with a three-dimensional crosslinked structure, enhancing heat, weather, and water resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If a compound with two epoxy groups is used to form linear polymer, then polymerization is achieved, but heat resistance is poor and bond strength is lost at high temperature

Engineering Contradiction:
Improvebond strengthVSAvoidheat resistance
Core Design Contradiction:
StrengthVSTemperature

Solution Approach 1:

The patent transitions from linear polymer structure (one-dimensional) to three-dimensional crosslinked network structure. The compound contains both epoxy groups and allyl groups that enable crosslinking through different mechanisms, creating a spatial network that maintains structural integrity at high temperatures, thereby resolving the heat resistance problem while preserving bond strength.

Inventive Principle:
Principle #17Another dimension (Dimensionality change)

Solution Approach 2:

The patent creates a composite polymer system by combining epoxy resin with the novel aryl compound containing both epoxy and allyl groups. This composite approach allows the epoxy groups to provide crosslinking for heat resistance while the allyl groups form additional crosslinks, resulting in a material that simultaneously achieves both strength and heat resistance.

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If low molecular weight hydrocarbon linking groups are used, then compound synthesis is simplified, but heat resistance and CVD film resistance are poor

Engineering Contradiction:
Improvesynthesis simplicityVSAvoidheat resistance
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The patent modifies the molecular weight parameter of the linking hydrocarbon groups, increasing them from low molecular weight (e.g., methyl) to high molecular weight (C3-C20). This parameter change maintains synthetic feasibility while dramatically improving heat resistance and CVD film resistance properties of the resulting polymer.

Inventive Principle:
Principle #35Parameter changes

3Temperature

If aryl compound with high molecular weight linking groups is used, then heat resistance is improved, but polymerization reactivity may be reduced

Engineering Contradiction:
Improveheat resistanceVSAvoidpolymerization reactivity
Core Design Contradiction:
TemperatureVSProductivity

Solution Approach 1:

The patent designs the aryl compound to possess multiple functional groups (epoxy groups and allyl groups) that can participate in different polymerization mechanisms. This multi-functionality ensures that even with high molecular weight linking groups, the compound maintains high polymerization reactivity through alternative reaction pathways, resolving the contradiction between heat resistance and reactivity.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 resulting polymer demonstrates improved strength, heat resistance, and water resistance, making it suitable for heat-resistant resin materials.

Implementation Method 1

The aryl compound having at least three glycidyl groups and at least three (meth)allyl groups in the molecule is polymerizable in two ways using (meth)allyl groups and oxirane rings. Since the aryl compound has at least three functional groups of each type in the molecule, the resulting polymer has a three-dimensional crosslinked structure.

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Implementation Method 2

Since the aryl compound has at least three functional groups of each type in the molecule, the resulting polymer has a three-dimensional crosslinked structure. A polymer as polymerized using such functional groups is further crosslinkable and curable.

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentUS9840484B2Aryl compound and making method
Publication Date: 2017.12.12 SHIN ETSU CHEMICAL CO LTD
  • US9840484B2 patent drawing
  • US9840484B2 patent drawing
  • US9840484B2 patent drawing

AI summary

An aryl compound terminated with at least three glycidyl groups and at least three (meth)allyl groups, having formula (1) wherein R1 is a C3-C20 hydrocarbon, R2 is hydrogen or methyl, and n is 3 or 4 is novel. It is prepared by reacting an aryl compound having at least three (meth)allyl-containing phenol groups with a 2-halomethyloxirane.