Hydroxy-Functionalized Triazine Crosslinkers for Fluoropolymer Curing

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Solution Overview

Problem

There is a need for novel curing systems for fluoropolymers that are more cost-effective, efficient, and have improved properties and performance.

Innovation Solution

The development of hydroxy-functionalized triazine compounds, which are synthesized through a reaction of vinyl ether monomers with ammonia to form amidine molecules, followed by heating to create a crosslinking agent for amorphous fluorinated polymers, allowing for the formation of curable compositions that can be cured into articles such as o-rings, seals, gaskets, hoses, or sheets.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional curing systems are used for fluoropolymers, then the existing properties can be maintained, but the curing efficiency and cost-effectiveness are insufficient

Engineering Contradiction:
Improvecuring efficiencyVSAvoidcost-effectiveness
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical parameters of the curing system by introducing hydroxy-functionalized triazine compounds with specific molecular structures (Formula I) that enable more efficient curing reactions. The compound's functional groups and molecular weight are optimized to achieve faster cure rates and better performance while maintaining cost-effectiveness.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite curing system by combining the hydroxy-functionalized triazine compound with amorphous fluorinated polymers containing vinylidene fluoride units. This composite approach leverages the complementary properties of both materials to achieve superior curing efficiency and performance characteristics.

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing curing agents are used, then the basic curing function is achieved, but the properties and performance of the cured articles are limited

Engineering Contradiction:
Improveproperties and performanceVSAvoidcuring efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent optimizes the chemical parameters of the curing agent by using triazine compounds with specific hydroxy functional groups and controlled molecular structures. This enables the cured articles to achieve enhanced physical properties, chemical resistance, and mechanical performance while maintaining efficient curing kinetics.

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 hydroxy-functionalized triazine compounds provide enhanced curing efficiency and improved properties in fluoropolymer compositions, resulting in high-performance articles with optimized physical characteristics.

Implementation Method 1

reacting a vinyl ether monomer according to Formula (II), with ammonia to form an amidine molecule

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

heating the amidine molecule to form the compound according to Formula (I)

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Implementation Method 3

an amorphous fluorinated polymer capable of being dehydrofluorinated

Methodology Applied
Scientific EffectDehydrofluorination: Pyrolysis

Data Source

PatentUS12428384B2Hydroxy-functionalized triazine compounds, curable fluoropolymer compositions comprising such compounds and cured articles therefrom
Publication Date: 2025.09.30 3M INNOVATIVE PROPERTIES CO
  • US12428384B2 patent drawing
  • US12428384B2 patent drawing
  • US12428384B2 patent drawing

AI summary

Described herein are compounds according to Formula (I) wherein each Rf is independently selected from a perfluorinated divalent group comprising 2 to 12 carbon atoms; and m is an integer independently selected from 1 to 3. A method of making the compound from a hydroxy-containing vinyl ether and excess ammonia is disclosed. In one embodiment, the hydroxy-functionalized triazine compound is used in a curable fluoropolymer composition and cured to form articles.