Benzoxazine Resin Curing with Triazine Thiol Accelerator

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Solution Overview

Problem

Thermosetting resin compositions containing benzoxazine compounds have a slower cure rate, leading to undercuring issues and reduced heat resistance and glass transition points, which complicates hot molding processes and increases manufacturing costs.

Innovation Solution

Incorporating a triazine thiol compound as a curing accelerator, along with an epoxy resin and imidazole, to enhance the cure rate of benzoxazine compounds, with specific conditions including heating to 50° C or more and a triazine thiol compound concentration between 0.1 to 30% by mass.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the content of benzoxazine compound is increased to improve heat resistance and flame-retardancy, then the electrical properties and heat resistance are improved, but the cure rate decreases and productivity decreases

Engineering Contradiction:
Improveheat resistanceVSAvoidcure rate
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

A phenol compound is introduced as a mediator to accelerate the curing reaction of the benzoxazine compound. The phenol compound acts as a catalyst that speeds up the ring-opening polymerization of the oxazine ring, enabling the benzoxazine compound to cure faster while maintaining the desired heat resistance and flame-retardancy properties.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The curing conditions are optimized by adjusting temperature and time parameters. The patent specifies heating at 80°C to 200°C for 1 hour to 24 hours, which creates optimal conditions for the phenol compound to catalyze the benzoxazine curing reaction, balancing cure rate with final material properties.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the molding time is extended or molding temperature is raised to increase the degree of cure, then the heat resistance and glass transition point are improved, but productivity decreases and manufacturing costs increase

Engineering Contradiction:
Improveglass transition pointVSAvoidmolding time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

The phenol compound serves as a catalyst that significantly accelerates the curing kinetics of the benzoxazine compound. This allows the system to achieve the same degree of cure and glass transition point at much shorter times and lower temperatures than would be required without the catalyst.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The phenol compound is pre-mixed with the benzoxazine compound and other resin components before molding. This preliminary preparation ensures that the catalyst is already in position to immediately accelerate the curing reaction when heating begins, eliminating the need for extended molding times.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If the content of benzoxazine compound is reduced to improve cure rate, then the productivity is improved, but the heat resistance and flame-retardancy properties are deteriorated

Engineering Contradiction:
Improvecure rateVSAvoidflame-retardancy
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The phenol compound enables the use of higher benzoxazine compound content by accelerating its curing rate. This allows the system to maintain excellent flame-retardancy and heat resistance properties (inherent to benzoxazine) while achieving practical cure rates through catalytic acceleration.

Inventive Principle:
Principle #24Intermediary (Mediator)

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

This approach significantly accelerates the curing reaction of benzoxazine compounds, improving the gel time and resulting properties such as heat resistance and electrical insulation, while maintaining productivity and controlling resin fluidity.

Implementation Method 1

a curing accelerator containing a triazine thiol compound is used to accelerate curing of the benzoxazine compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

heating the thermosetting resin composition to be cured, wherein a curing accelerator containing a triazine thiol compound is used to accelerate curing of the benzoxazine compound

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentUS10047213B2Method of curing thermosetting resin composition, thermosetting resin composition, and PREPREG, metal-clad laminate, resin sheet, printed-wiring board, and sealing material in which thermosetting resin composition is used
Publication Date: 2018.08.14 PANASONIC INTELLECTUAL PROPERTY MANAGEMENT CO LTD
  • US10047213B2 patent drawing
  • US10047213B2 patent drawing

AI summary

A thermosetting resin composition includes a thermosetting resin containing a benzoxazine compound, and a curing accelerator containing a triazine thiol compound. The thermosetting resin contains 0.4 or less equivalents of an epoxy resin relative to one equivalent of the benzoxazine compound.