Heterocyclic Imine Functionalized Polydienes for Tire Hysteresis Reduction

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Solution Overview

Problem

Current rubber vulcanizates used in tire manufacturing exhibit high hysteresis, leading to increased rolling resistance and cold flow issues, which are unpredictable when functionalized with various polymers and catalyst systems, particularly with lanthanide-based catalysts that produce polymers with linear backbones.

Innovation Solution

The method involves polymerizing conjugated diene monomers to form reactive polymers, which are then functionalized with imine compounds containing a heterocyclic group and a hydrocarbyloxy-substituted or silyloxy-substituted aryl group, reducing hysteresis and cold flow by interacting with filler particles and agglomerates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If lanthanide-based catalyst systems are used to polymerize conjugated diene monomers, then the polymers exhibit high cis-1,4-linkage content and good tensile properties, but the polymers display high cold flow due to linear backbone structure

Engineering Contradiction:
Improvetensile propertiesVSAvoidcold flow
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of polymer chains through functionalization. By introducing heterocyclic imine groups with specific substituents (aromatic rings, heteroatoms, hydrocarbyloxy or silyloxy groups), the polymer's physical properties are altered without changing the fundamental cis-1,4-linkage structure. This functionalization reduces cold flow while preserving tensile properties achieved by lanthanide-based polymerization.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite functional structure by combining the polydiene backbone with heterocyclic imine functional groups. The resulting functionalized polydiene exhibits properties that are a combination of the original polymer's mechanical strength and the functional group's ability to reduce cold flow, effectively creating a material with optimized performance characteristics.

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If functionalized polymers are used to reduce hysteresis, then energy loss is reduced, but the predictability of hysteresis reduction is poor with different functional groups

Engineering Contradiction:
ImprovehysteresisVSAvoidpredictability
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent systematically varies specific parameters of the functional groups (heterocyclic structure, imine linkage, aromatic substituents, heteroatom types) to achieve consistent hysteresis reduction. By focusing on this specific class of compounds with defined structural features, the patent establishes predictable structure-property relationships that enable reliable hysteresis reduction.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by introducing specific functional groups at the chain ends of polymer molecules. These localized functional groups interact with filler particles and free chain ends at specific sites, producing consistent hysteresis reduction effects that are predictable based on the functional group's chemical characteristics.

Inventive Principle:
Principle #3Local quality

3Loss of energy

If functionalizing agents are used to modify reactive polymers, then hysteresis may be reduced, but the compatibility between functionalizing agent and polymer type is unpredictable

Engineering Contradiction:
ImprovehysteresisVSAvoidcompatibility
Core Design Contradiction:
Loss of energyVSAdaptability or versatility

Solution Approach 1:

The patent achieves universality by demonstrating that heterocyclic imine compounds with the specified structural features can effectively functionalize different types of polydienes (cis-1,4-polydienes from lanthanide catalysts and other polydienes) to reduce hysteresis. The functional group class proves versatile across different polymer substrates.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent establishes structure-activity relationships by varying parameters within the heterocyclic imine compound class (different heteroatoms, aromatic substituents, hydrocarbyloxy or silyloxy groups) to optimize compatibility and hysteresis reduction across different polymer types, creating a versatile functionalizing agent platform.

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

This approach results in tire components with reduced hysteresis and cold flow, enhancing their mechanical properties and manufacturing efficiency by stabilizing the polymer structure and improving interaction with fillers.

Implementation Method 1

The functional group of the functionalized polymer may reduce the number of free polymer chain ends via interaction with filler particles

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentEP2969593B1Polymers functionalized with heterocyclic imines
Publication Date: 2020.11.04 BRIDGESTONE CORP
  • EP2969593B1 patent drawingFigure 1
  • EP2969593B1 patent drawingFigure 2
  • EP2969593B1 patent drawing

AI summary

A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with an imine compound containing a heterocyclic group and a hydrocarbyloxy-substituted or silyloxy-substituted aryl group.