Substituted Epoxide 1,3-Dipolar Compounds for Diene Rubber Rupture Strength

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Solution Overview

Problem

Modified diene elastomers used in rubber compositions for tires often exhibit degraded rupture properties, which are crucial for withstanding high stresses and strains during rolling, while also requiring low rolling resistance.

Innovation Solution

The use of 1,3-dipolar compounds bearing a specific substituted epoxide group for grafting onto diene polymers, improving rupture properties without compromising hysteresis properties, involves a process where these compounds react with diene polymers to form a crosslinked rubber composition that includes a reinforcing filler and a crosslinking system.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a 1,3-dipolar compound bearing a glycidyl group is used to modify diene elastomers, then crosslinking capability is improved, but rupture properties are degraded

Engineering Contradiction:
Improvecrosslinking capabilityVSAvoidrupture properties
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The patent changes the chemical structure parameters of the epoxide group by introducing specific substituents (alkyl groups with 1-6 carbon atoms, aryl groups with 6-12 carbon atoms, or cyclic groups) at defined positions on the epoxide ring. This structural modification transforms the reactive glycidyl group into a less reactive but more mechanically stable substituted epoxide group, resolving the contradiction between crosslinking capability and rupture properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite functional group by combining the 1,3-dipolar compound framework with a substituted epoxide group. This composite structure integrates the crosslinking function of the epoxide with the mechanical stability provided by the substituted carbon framework, achieving both crosslinking capability and improved rupture properties

Inventive Principle:
Principle #40Composite materials

2Strength

If crosslinking density is increased to improve rupture properties, then hysteresis properties are compromised

Engineering Contradiction:
Improverupture propertiesVSAvoidhysteresis properties
Core Design Contradiction:
StrengthVSLoss of energy

Solution Approach 1:

The patent modifies the reactivity parameters of the epoxide group through substitution, creating a balanced crosslinking rate that achieves sufficient crosslinking density for rupture strength without excessive crosslinking that would increase hysteresis. The substituted epoxide groups provide controlled reactivity that prevents over-crosslinking

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 rubber composition demonstrates enhanced rupture properties and processing ease, maintaining low hysteresis and rolling resistance, thus improving the performance and implementation of tire materials.

Implementation Method 1

a process for modifying a diene polymer, notably a diene elastomer, via a grafting reaction

Methodology Applied
Scientific EffectGrafting reaction: Chemical Bonding

Implementation Method 2

These elastomers thus obtained may be used crosslinked in a rubber composition

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentUS11952438B21,3-dipolar compound comprising an epoxide group
Publication Date: 2024.04.09 MICHELIN & CO (CIE GEN DES ESTAB MICHELIN)
  • US11952438B2 patent drawing
  • US11952438B2 patent drawing
  • US11952438B2 patent drawing

AI summary

A 1,3-dipolar compound including an epoxide group is provided. The epoxide group is a 3-membered ether ring in which a first member is a carbon atom having an attachment to the dipole of the 1,3-dipolar compound and a second member is a tertiary or quaternary carbon. The use of the 1,3-dipolar compound in the modification of a diene polymer makes it possible to improve the rupture properties of a rubber composition comprising the modified polymer, without the expense of its hysteresis properties, while at the same time improving its implementation.