Phosphorus-Containing 1,3-Dipolar Compound for Rubber Reinforcement

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Solution Overview

Problem

Existing polymer modifiers fail to effectively balance hysteresis and stiffness in rubber compositions containing fillers like carbon black or silica, leading to unsuitable material properties for applications such as tires.

Innovation Solution

A 1,3-dipolar compound with a phosphorus-containing group is used to graft onto unsaturated polymers, forming pendant phosphorus-containing groups and isoxazoline rings, which improves filler dispersion and modifies the polymer chain, thereby optimizing the compromise between hysteresis and stiffness in rubber compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If conventional polymer modifiers are used to functionalize the polymer, then filler dispersion is improved, but stiffness of the cured composition decreases

Engineering Contradiction:
Improvefiller dispersionVSAvoidstiffness
Core Design Contradiction:
Stability of the object's compositionVSStrength

Solution Approach 1:

The invention changes the chemical parameters of the modifier by introducing a phosphorus-containing group with specific formula (I) featuring P=O and P-O-C bonds. This specific chemical structure modifies the polymer-filler interaction to simultaneously improve dispersion and maintain stiffness, resolving the contradiction between filler dispersion and composition stiffness.

Inventive Principle:
Principle #35Parameter changes

2Loss of energy

If filler dispersion is improved to lower hysteresis, then hysteresis decreases, but stiffness of the cured composition decreases

Engineering Contradiction:
ImprovehysteresisVSAvoidstiffness
Core Design Contradiction:
Loss of energyVSStrength

Solution Approach 1:

The phosphorus-containing group with formula (I) changes the chemical parameters of the polymer modifier, creating optimal interactions that reduce hysteresis while preserving stiffness. The specific P=O and P-O-C bonding characteristics enable this dual benefit by modifying how the polymer matrix interacts with filled particles.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If chemical modification of the polymer is performed, then filler dispersion and homogeneity are improved, but the compromise between hysteresis and stiffness becomes unsuitable

Engineering Contradiction:
ImprovehomogeneityVSAvoidhysteresis-stiffness compromise
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The invention performs chemical modification using a specifically designed phosphorus-containing compound with formula (I). The P=O and P-O-C functional groups provide optimal chemical parameters that achieve homogeneous filler distribution while maintaining the appropriate hysteresis-stiffness balance for tire applications.

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 compositions exhibit improved reinforcement, cohesion, and reduced hysteresis without compromising rigidity, resulting in enhanced tire performance.

Implementation Method 1

The chemical reactions for modifying an unsaturated polymer include the reactions of grafting of a compound

Methodology Applied
Scientific EffectGrafting reaction: Chemical Bonding

Implementation Method 2

Chemical modification of a polymer may improve the dispersion of the filler in the polymer

Methodology Applied
Scientific EffectDispersion: Dispersion (of waves)

Data Source

PatentUS10787471B21,3-dipolar compound bearing a phosphorus-containing group and a dipole containing a nitrogen atom
Publication Date: 2020.09.29 MICHELIN & CO (CIE GEN DES ESTAB MICHELIN)
  • US10787471B2 patent drawing
  • US10787471B2 patent drawing
  • US10787471B2 patent drawing

AI summary

A 1,3-dipolar compound bearing at least a phosphorus-containing group and a dipole containing a nitrogen atom is provided. A method for grafting the 1,3-dipolar compound on an unsaturated polymer, a diene polymer comprising, along the polymer chain, at least one pendant phosphorus-containing group, and a rubber composition based on a diene elastomer and the 1,3-dipolar compound optionally pre-grafted on the diene elastomer are also provided. The 1,3-dipolar compound allows access to rubber compositions reinforced with an inorganic filler that have a compromise of improved properties, namely hysteresis, stiffness in the cured state and reinforcement.