Modified Polymer Masterbatch for Room-Temperature 1,3-Dipolar Grafting

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Solution Overview

Problem

Current processes for modifying polymers using 1,3-dipolar grafting agents are complex, costly, and yield lower grafting efficiencies, especially when using natural rubber, and often require additional steps like heat treatment or epoxidation, which increase industrial costs and process complexity.

Innovation Solution

A process involving the use of organophosphorus additives such as phosphoric acid triesters, phosphonates, and phosphinates to facilitate the grafting of 1,3-dipolar agents onto polymers at room temperature without the need for heat treatment, improving grafting yields significantly across various polymer types, including natural rubber and synthetic polyisoprene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If heat treatment step is added to improve grafting efficiency, then grafting yield is improved, but process complexity and manufacturing cost increase

Engineering Contradiction:
Improvegrafting yieldVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent introduces a catalyst as an intermediary substance that mediates the grafting reaction between the polymer and 1,3-dipolar grafting agent. The catalyst enables the reaction to proceed efficiently at room temperature without requiring heat treatment, thus improving grafting yield while avoiding additional process complexity from thermal processing steps.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by introducing a catalyst that allows the grafting reaction to occur at room temperature instead of requiring elevated temperatures. This parameter change (temperature) eliminates the need for heat treatment steps while maintaining or improving grafting efficiency, thereby reducing process complexity.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If epoxidation step is added to improve grafting yield for natural rubber, then grafting efficiency is improved, but manufacturing cost increases

Engineering Contradiction:
Improvegrafting yieldVSAvoidmanufacturing cost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent uses a catalyst as an intermediary that directly facilitates the grafting reaction on natural rubber without requiring prior epoxidation modification. The catalyst enables efficient grafting of 1,3-dipolar compounds onto the natural rubber double bonds, eliminating the need for the additional epoxidation step and associated manufacturing costs.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

Instead of performing preliminary epoxidation modification before grafting, the patent applies a catalyst that enables direct grafting of 1,3-dipolar compounds onto the natural rubber. This eliminates the preliminary epoxidation action while achieving equal or better grafting yields, thereby reducing manufacturing complexity and cost.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If multiple reaction steps are used to achieve high grafting yield, then grafting efficiency is improved, but process simplicity is reduced

Engineering Contradiction:
Improvegrafting yieldVSAvoidprocess simplicity
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent merges the catalyst activation function with the grafting reaction into a single integrated process step. The catalyst simultaneously activates the 1,3-dipolar grafting agent and facilitates its reaction with the polymer at room temperature, combining what would otherwise require separate heating and reaction steps into one simple operation.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The catalyst serves as an intermediary that enables the grafting reaction to proceed in a single step at room temperature. By introducing this mediating substance, the patent consolidates multiple potential steps (heating, activation, reaction) into one simple mixing operation, thereby improving process simplicity while maintaining high grafting yields.

Inventive Principle:
Principle #24Intermediary (Mediator)

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

This approach simplifies the polymer modification process, enhances grafting yields, and reduces costs by eliminating the need for heat treatment, while maintaining or improving grafting efficiency regardless of the polymer's chemical nature.

Implementation Method 1

contact at least one starting polymer comprising at least one carbon-carbon unsaturation with at least one 1,3-dipolar grafting agent bearing at least one nitrile oxide dipole in the presence of at least one organophosphorus additive

Methodology Applied
Scientific EffectGrafting reaction: Chemical Bonding

Data Source

PatentEP4081577B1Masterbatch based on a modified polymer and an organophosphorus additive, and method for manufacturing same
Publication Date: 2024.05.29 MICHELIN & CO (CIE GEN DES ESTAB MICHELIN)
  • EP4081577B1 patent drawing
  • EP4081577B1 patent drawing
  • EP4081577B1 patent drawing

AI summary

The invention relates to a method for manufacturing a masterbatch, comprising the following steps: (a) placing at least one initial polymer comprising at least one carbon-carbon unsaturation in contact with at least one 1,3-dipolar grafting agent having at least one nitrile oxide dipole in the presence of at least one organophosphorus additive selected from the group consisting of phosphoric acid triesters, phosphonates, phosphinates, phosphine oxides and mixtures of these compounds, (b) retrieving the masterbatch obtained in the preceding step. The invention also relates to the masterbatch and the compositions containing same and to tyres comprising such a composition.