Polyfunctional vinyl resin and method for producing same, polyfunctional vinyl resin composition, cured article, prepreg, resin sheet, and laminated plate

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Solution Overview

Problem

Existing vinyl benzyl ether resins fail to provide cured articles with sufficient heat resistance and low dielectric loss tangent after severe thermal history, especially in high-frequency applications, and are inadequate in terms of reliability and processability.

Innovation Solution

A polyfunctional vinyl resin is synthesized through the aromatic vinylation of a phenolic hydroxy group of a polyhydric hydroxy resin with a dicyclopentenyl group, derived from a reaction between 2,6-disubstituted phenol and dicyclopentadiene, resulting in a resin with a specific molecular structure that maintains low dielectric constant and loss tangent while enhancing thermal conductivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If vinyl benzyl ether resins are used to improve heat resistance, then glass transition temperature increases, but dielectric loss tangent increases and dielectric characteristics deteriorate

Engineering Contradiction:
Improveglass transition temperatureVSAvoiddielectric loss tangent
Core Design Contradiction:
TemperatureVSLoss of energy

Solution Approach 1:

The patent changes the chemical structure parameters of the resin by introducing specific aromatic rings (naphthalene, biphenyl) and controlling the number and position of vinyl groups and hydroxy groups. This structural parameter change allows achieving both high glass transition temperature and low dielectric loss tangent simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure combining multiple aromatic rings (naphthalene, biphenyl) with vinyl groups and hydroxy groups in specific configurations. This composite structure provides both thermal resistance and excellent dielectric properties

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If severe thermal history is applied to improve heat resistance, then thermal stability increases, but dielectric characteristics change and reliability decreases

Engineering Contradiction:
Improvethermal stabilityVSAvoiddielectric characteristic stability
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent designs the resin structure beforehand with built-in thermal stability features - specific aromatic ring structures and crosslinkable groups that prevent excessive dielectric loss tangent increase even when exposed to severe thermal history, cushioning against reliability deterioration

Inventive Principle:
Principle #11Beforehand cushioning (Prior cushioning)

3Temperature

If conventional vinyl benzyl ether resins are used, then heat resistance is improved, but initial dielectric characteristics are insufficient

Engineering Contradiction:
Improveheat resistanceVSAvoidinitial dielectric characteristics
Core Design Contradiction:
TemperatureVSLoss of energy

Solution Approach 1:

The patent introduces local structural features - specific aromatic rings with vinyl and hydroxy groups at particular positions - that locally provide both thermal resistance and low dielectric loss tangent properties, achieving excellent initial dielectric characteristics while maintaining heat resistance

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 resin exhibits high thermal conductivity, low dielectric constant, and low dielectric loss tangent, maintaining excellent dielectric characteristics even under high-temperature thermal history, thus ensuring high reliability in electronic materials for high-speed communication devices.

Implementation Method 1

a polyfunctional vinyl resin obtained by subjecting a hydroxy group of at least one kind selected from the group consisting of: a phenol aralkyl resin; a naphthol aralkyl resin; a biphenyl-type phenol novolac resin; and a biphenyl-type naphthol novolac resin to vinyl benzyl etherification

Methodology Applied
Scientific EffectVinyl benzyl etherification: Chemical Bonding

Data Source

PatentUS12378345B2Polyfunctional vinyl resin and method for producing same, polyfunctional vinyl resin composition, cured article, prepreg, resin sheet, and laminated plate
Publication Date: 2025.08.05 NIPPON STEEL CHEM & MATERIAL CO LTD
  • US12378345B2 patent drawing
  • US12378345B2 patent drawing
  • US12378345B2 patent drawing

AI summary

Provided is a resin material showing a high thermal conductivity and having high heat resistance while having a low dielectric constant and a low dielectric loss tangent. The material is a polyfunctional vinyl resin, which is represented by the following general formula (1):where R1s each independently represent a hydrocarbon group having 1 to 8 carbon atoms, R2s each independently represent a hydrogen atom or a dicyclopentenyl group, and at least one thereof represents a dicyclopentenyl group, Xs each independently represent a hydrogen atom or a vinyl group-containing aromatic group represented by the formula (1a), and at least one thereof represents a vinyl group-containing aromatic group, ā€œnā€ represents a number of repetitions, and the average thereof is a number of from 1 to 5, and Ar represents an aromatic ring.