Polyphenylene ether copolymer oligomer solubility

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Solution Overview

Problem

There is a need for poly(phenylene ether) polymers and oligomers that more efficiently incorporate dihydric phenol, as existing additives face challenges in dissolving in thermosetting resin and achieving optimal toughness and compatibility with polyamide resins.

Innovation Solution

The development of a copolymer synthesized by copolymerizing 2,4,6-trimethylresorcinol with a monohydric phenol, which exhibits efficient incorporation of 2,4,6-trimethylresorcinol, and is used in conjunction with a solvent and thermosetting resin to enhance compatibility and toughness.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If poly(phenylene ether) polymers with high molecular weight are used to increase thermoset toughness, then toughness improvement is achieved, but dissolving in thermosetting resin becomes difficult

Engineering Contradiction:
Improvethermoset toughnessVSAvoiddissolving in thermosetting resin
Core Design Contradiction:
StrengthVSEase of manufacture

Solution Approach 1:

The patent segments the high molecular weight polymer into lower molecular weight oligomers (number average molecular weight of 500 to 5,000), which are easier to dissolve while maintaining toughness enhancement capability. This segmentation allows the additive to disperse more effectively in the thermosetting resin matrix.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes key parameters of the poly(phenylene ether) additive: reducing molecular weight from high polymer range to oligomer range (500-5,000), and increasing hydroxyl functionality to about two hydroxyl groups per molecule. These parameter changes improve solubility in thermosetting resins while preserving the ability to enhance toughness.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If lower molecular weight poly(phenylene ether) oligomers are used to improve dissolving, then solubility in thermosetting resin improves, but a preference evolves for higher hydroxyl functionality which complicates incorporation of dihydric phenol

Engineering Contradiction:
Improvedissolving in thermosetting resinVSAvoidincorporation of dihydric phenol
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent optimizes the hydroxyl functionality parameter to about two hydroxyl groups per molecule, which provides adequate solubility in thermosetting resins while enabling effective incorporation of dihydric phenol through copolymerization. This parameter optimization balances solubility requirements with dihydric phenol incorporation efficiency.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a copolymer composite structure incorporating 2,4,6-trimethylresorcinol (a dihydric phenol) with other phenolic units in the oligomer chain. This composite approach at the molecular level achieves efficient incorporation of the dihydric phenol while maintaining the desired oligomer properties for solubility.

Inventive Principle:
Principle #40Composite materials

3Strength

If hydroxyl-diterminated poly(phenylene ether) oligomers are used to achieve better thermoset toughness, then toughness for given amount improves, but efficient incorporation of dihydric phenol remains insufficient

Engineering Contradiction:
Improvethermoset toughnessVSAvoidincorporation efficiency of dihydric phenol
Core Design Contradiction:
StrengthVSQuantity of substance

Solution Approach 1:

The patent synthesizes copolymers containing 2,4,6-trimethylresorcinol units integrated into the poly(phenylene ether) oligomer structure. This molecular-level composite structure achieves efficient incorporation of the dihydric phenol (2,4,6-trimethylresorcinol) while maintaining the oligomer's toughness-enhancing properties in thermosetting resins.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent changes the composition parameters by incorporating specific ratios of 2,4,6-trimethylresorcinol with other phenolic monomers to optimize both the dihydric phenol incorporation efficiency and the resulting thermoset toughness. The copolymer structure allows precise control of dihydric phenol content.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3519481B1Phenylene ether copolymer and compositions comprising same
Publication Date: 2023.04.19 SHPP GLOBAL TECH BV
  • EP3519481B1 patent drawingFigure 1~2
  • EP3519481B1 patent drawingFigure 3
  • EP3519481B1 patent drawingFigure 4

AI summary

A copolymer having the structure (I) wherein Q1, Q2, Q3, Q4, m, and n are defined herein. The copolymer can be formed by oxidative copolymerization of 2,4,6-trimethyIresorcinoI with a monohydric phenol. Also describes are a composition comprising the copolymer and a solvent, and a composition comprising the copolymer and a thermosetting resin.