Modified Cyanate Esters for Low Water Uptake Resins

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Solution Overview

Problem

Current technologies fail to efficiently and cost-effectively produce high-performance composite resins from renewable resources, and they suffer from significant water uptake issues, which are detrimental in humid environments, particularly for naval weapon platforms.

Innovation Solution

Development of modified single-ring cyanate esters that can tailor and control the glass-transition temperature (Tg) and water uptake of cured resins, using bioaromatics like phloroglucinol, and altering the ester group from propyl to ethylhexyl to dramatically reduce water absorption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional cyanate ester resins are used, then good mechanical properties are achieved, but water uptake is high which reduces performance in humid environments

Engineering Contradiction:
Improveperformance in humid environmentsVSAvoidwater uptake
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the cyanate ester monomers by using modified single-ring structures with specific ester groups (propyl, ethylhexyl, butyl) and controlling molecular weight and purity. These parameter changes result in cured resins with dramatically reduced water uptake (0.83-2.93 wt% range) while maintaining high Tg values (140-229°C), thereby improving reliability in humid environments

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite resin systems by combining modified single-ring cyanate esters with appropriate hardeners and fillers. The composite structure integrates the hydrophobic modified cyanate ester matrix with reinforcing materials, achieving both low water uptake and high mechanical performance suitable for naval weapon platforms

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If renewable resources like phloroglucinol are used to produce cyanate esters, then sustainability is improved, but production efficiency and cost-effectiveness are insufficient

Engineering Contradiction:
Improveuse of renewable resourcesVSAvoidproduction efficiency
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent performs preliminary purification and characterization of bioaromatic feedstocks like phloroglucinol before cyanate ester synthesis. By pre-processing the renewable resources to ensure high purity and appropriate molecular weight distribution, the subsequent curing process achieves consistent high performance with reduced trial-and-error, thereby improving overall production efficiency and cost-effectiveness

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent optimizes synthesis parameters including reaction temperature, catalyst selection, and monomer purity control when producing cyanate esters from renewable resources. These parameter changes enable efficient conversion of bioaromatics to high-performance resin precursors, making the sustainable production route both economically and technologically viable

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If the ester group is changed from propyl to ethylhexyl, then water uptake is dramatically reduced, but synthesis complexity increases

Engineering Contradiction:
Improvewater absorptionVSAvoidsynthesis process complexity
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent systematically varies the ester group parameter (propyl, ethylhexyl, butyl) in the cyanate ester monomers and correlates this structural parameter with water uptake performance. The ethylhexyl ester group, with its longer carbon chain and branched structure, provides superior hydrophobicity and lowest water uptake (0.83 wt%), despite requiring slightly more complex synthesis steps for purification and characterization

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 modified cyanate esters exhibit remarkably low water uptake and maintain Tg in wet conditions, providing a significant performance advantage for naval applications while being made from sustainable resources, with data showing a reduction in water uptake from 2.93 wt-% to 0.83 wt-%, and demonstrating full curing and thermal stability.

Implementation Method 1

thermal curing of the 3,5-bis(cyanato)benzoate esters to form composite parts

Methodology Applied
Scientific EffectThermal curing:

Implementation Method 2

altering the ester group from propyl to ethylhexyl to dramatically reduce water absorption

Methodology Applied
Scientific EffectHydrophobic effect: Hydrophobe

Data Source

PatentUS9434685B1Preparation and thermal curing of single-ring bis(cyanate) ester monomers
Publication Date: 2016.09.06 THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE NAVY
  • US9434685B1 patent drawing
  • US9434685B1 patent drawing
  • US9434685B1 patent drawing

AI summary

A class of modified single-ring cyanate esters which have shown the ability to tailor and control the glass-transition (Tg) of the cured resins as well as the water uptake.