Imidazole Catalyst Resin Composition for Low-Temperature Curing

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The addition of imidazole compounds in cyanate resins and bismaleimide triazine resins improves curing speed and productivity but compromises storage stability of prepregs.

Innovation Solution

A resin composition comprising a specific imidazole compound, epoxy compound, and cyanate compound, allowing for low-temperature drying and lamination pressing while maintaining storage stability, by utilizing an imidazole compound with bulky substituents that exhibit high molecular motion energy at elevated temperatures for catalytic activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If imidazole compounds are added to cyanate resins or BT resins to increase curing speed, then productivity is improved, but storage stability of prepregs is lowered

Engineering Contradiction:
Improvecuring speedVSAvoidstorage stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention changes the molecular structure parameters of the imidazole compound by introducing bulky substituents (specifically tert-butyl groups at positions 2 and 5, and phenyl groups at positions 1 and 3) to modify the catalytic activity characteristics. This structural parameter change enables the catalyst to remain inactive at storage temperatures while becoming active at curing temperatures, thus resolving the contradiction between storage stability and curing speed

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite catalytic system by combining the specific imidazole compound with epoxy resin in defined proportions (0.01-10 wt% imidazole compound and 90-99.99 wt% epoxy resin). This composite formulation achieves synergistic effects where the epoxy resin matrix provides stability while the imidazole compound provides controlled catalytic activity, simultaneously improving both storage stability and curing speed

Inventive Principle:
Principle #40Composite materials

2Temperature

If imidazole compounds are added to enable low-temperature curing in short time, then drying and lamination pressing can be performed at low temperatures, but storage stability is compromised

Engineering Contradiction:
Improvecuring temperatureVSAvoidstorage stability
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The invention modifies the activation temperature parameter of the imidazole compound through structural design with bulky substituents. The tert-butyl groups create steric hindrance that prevents catalytic activity at low temperatures (storage conditions) while allowing activity at elevated temperatures (curing conditions), thus enabling low-temperature curing capability without compromising storage stability

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 resin composition enables rapid curing at low temperatures while maintaining the storage stability of prepregs, achieving a balance between productivity and storage stability through the use of a specific imidazole compound that suppresses catalytic activity at low temperatures.

Implementation Method 1

Imidazole compounds have been proposed as such catalysts. The addition of imidazole compounds in the resins leads to the development of catalytic activity that can realize curing of resins at low temperatures in a short time

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a resin composition comprising: an imidazole compound (A) represented by formula (I); an epoxy compound (B); and a cyanate compound (C1)

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP2562196B1Thermosetting composition
Publication Date: 2018.02.21 MITSUBISHI GAS CHEM CO INC
  • EP2562196B1 patent drawing
  • EP2562196B1 patent drawing
  • EP2562196B1 patent drawing

AI summary

There is provided a resin composition that can allow a drying step after impregnation coating of a prepreg and lamination pressing to be performed at low temperatures in a short time and, at the same time, can maintain storage stability of the prepreg. The resin composition according to the present invention comprises (A) an imidazole compound represented by formula (I), (B) an epoxy compound, and (C1) a cyanate compound or (C2) a BT resin. In the formula, R1 and R2 each independently represent an alkyl group having 3 to 18 carbon atoms, an alkenyl group having 3 to 18 carbon atoms, an alkoxyl group having 3 to 18 carbon atoms, or a substituted or unsubstituted aromatic substituent having 6 to 14 carbon atoms; and R3 represents hydrogen, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aromatic substituent having 6 to 14 carbon atoms, or a halogen group.