Triphenylalkane Tris(allyl ether) Curing Agent Volatilization

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Solution Overview

Problem

Triallyl isocyanurate, used as a curing agent for thermosetting resins, volatilizes at high temperatures, leading to decreased resin quality, equipment contamination, and reduced production yield, while existing compounds with allyl groups offer high heat resistance but unsatisfactory dielectric properties.

Innovation Solution

A tris(allyl ether) compound with a triphenylalkane backbone and a substituent at the ortho position of the benzene ring, which prevents hydroxy group formation during heating, maintaining high heat resistance and improving dielectric properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If triallyl isocyanurate is used as a curing agent for thermosetting resins, then the curing function is provided, but the compound volatilizes at high temperatures causing equipment contamination and reduced production yield

Engineering Contradiction:
Improvecuring functionVSAvoidvolatilization and contamination
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical structure parameters of the curing agent by introducing a triphenylalkane backbone with allyloxy groups at specific positions. This structural modification raises the boiling point and reduces volatilization at curing temperatures while maintaining the allyl groups necessary for crosslinking reactions with thermosetting resins.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The compound combines multiple functional groups (allyl groups for crosslinking, triphenylalkane backbone for thermal stability, and ether linkages for flexibility) into a single molecular structure. This composite approach achieves both high-temperature resistance and effective curing function simultaneously.

Inventive Principle:
Principle #40Composite materials

2Temperature

If existing compounds with allyl groups are used to achieve high heat resistance, then volatilization is suppressed, but dielectric properties are not satisfactory

Engineering Contradiction:
Improveheat resistanceVSAvoiddielectric properties
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The invention optimizes specific positions on the benzene rings by placing allyloxy groups at the 2, 4, and 6 positions (with R1-R6 representing different substituents). This localized arrangement of functional groups achieves the right balance between heat resistance (through the rigid triphenylalkane core) and dielectric properties (through the strategically positioned ether and allyl groups).

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The compound modifies physical and chemical parameters including molecular weight, polarity, and spatial arrangement of functional groups. These parameter changes improve dielectric properties while the triphenylalkane backbone maintains high heat resistance.

Inventive Principle:
Principle #35Parameter changes

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 tris(allyl ether) compound effectively suppresses volatilization and enhances dielectric properties, making it suitable for high-reliability applications in electronic components and as a curing agent for epoxy and bismaleimide resins, while maintaining high heat resistance.

Implementation Method 1

the formation of a hydroxy group due to a Claisen rearrangement during heating can be prevented

Methodology Applied
Scientific EffectClaisen rearrangement:

Data Source

PatentUS20240116840A1Novel tris(allyl ether) compound having triphenylalkane backbone
Publication Date: 2024.04.11 HONSHU CHEM INDAL
  • US20240116840A1 patent drawing
  • US20240116840A1 patent drawing
  • US20240116840A1 patent drawing

AI summary

An object is to provide a compound that can be a novel curing agent. The compound suppresses volatilization of the curing agent that can lead to a decrease in function of a prepreg, contamination of equipment for producing the prepreg, and in addition a decrease in production yield of the prepreg, and further contributes to improving dielectric properties. As a solution, a tris(allyl ether) compound represented by general formula (1) below is provided.