Oxazine Compound with Triple Bonds for Thermal Stability

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Solution Overview

Problem

Current benzoxazine compounds used in electronic materials lack sufficient thermal decomposition resistance and dielectric properties, particularly due to the generation of aniline-derived decomposed gases during ring-opening, which limits their long-term thermal durability.

Innovation Solution

An oxazine compound with an aromatic ring structure and multiple carbon-carbon triple bond structures is developed, incorporating specific functional groups to enhance thermal decomposition resistance and dielectric properties, forming a dense crosslinked structure upon curing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If benzoxazine is prepared from aniline and phenol compounds, then the compound can undergo ring-opening polymerization by heating, but aniline-derived decomposed gases are generated reducing thermal decomposition resistance

Engineering Contradiction:
Improveheat resistanceVSAvoidthermal decomposition resistance
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent changes the chemical composition parameters by replacing aniline with aromatic diamines having specific structures (Formulae 1-3), which fundamentally alters the decomposition behavior. This parameter change eliminates the generation of aniline-derived decomposed gases while maintaining the ring-opening polymerization capability and heat resistance of benzoxazine compounds.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining aromatic diamine components with specific phenol compounds and formaldehyde. These composite structures (Formulae 4-6) integrate multiple functional groups including carbon-carbon triple bonds that enhance both heat resistance and thermal decomposition resistance simultaneously, resolving the contradiction between these two properties.

Inventive Principle:
Principle #40Composite materials

2Temperature

If conventional benzoxazine compounds are used, then they exhibit high heat resistance through strong hydrogen bonding, but they lack sufficient dielectric properties and show high moisture absorptivity

Engineering Contradiction:
Improveheat resistanceVSAvoiddielectric properties
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent introduces carbon-carbon triple bond structures and specific aromatic ring configurations into the benzoxazine molecular structure. These structural parameter changes reduce the polarity and hydrogen bonding density compared to conventional benzoxazines, thereby improving dielectric properties and reducing moisture absorptivity while preserving heat resistance through the aromatic backbone structure.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local structural modifications by introducing specific functional groups (carbon-carbon triple bonds, aromatic diamine moieties) at strategic positions within the molecular structure. These localized quality changes affect specific properties (dielectric constant, moisture absorption) without compromising the overall heat resistance provided by the benzoxazine core structure.

Inventive Principle:
Principle #3Local quality

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 oxazine compound exhibits improved thermal decomposition resistance, dielectric properties, and low hygroscopicity, making it suitable for high-heat applications such as semiconductor sealing materials, circuit boards, and fiber-reinforced resins with enhanced thermal stability.

Implementation Method 1

undergoes ring-opening polymerization by heating by itself

Methodology Applied
Scientific EffectRing-opening polymerization:

Implementation Method 2

exhibits high heat resistance and low linear expansion due to a strong hydrogen bonding structure formed in a crosslinked structure

Methodology Applied
Scientific EffectHydrogen bonding:

Data Source

PatentUS11117872B2Oxazine compound, composition and cured product
Publication Date: 2021.09.14 DIC CORP
  • US11117872B2 patent drawing
  • US11117872B2 patent drawing
  • US11117872B2 patent drawing

AI summary

The present invention provides an oxazine compound having a specific structure, which contains a group having an aromatic ring structure and a plurality of specified carbon-carbon triple bond structure. The present invention further provides a composition containing the oxazine compound having a specific structure of the present invention, a cured product containing the composition, and a laminate having the layer of the cured product. The present invention further still provides a composition for a heat-resistant material and a composition for an electronic material, which contain the composition containing the oxazine compound of the present invention.