Functionalized Polymers with Protected Oxime Cyano Groups for Low Hysteresis Tires

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Solution Overview

Problem

Existing rubber vulcanizates for tires exhibit high hysteresis, leading to increased rolling resistance and energy loss, which is unpredictable with current functionalized polymers and catalyst systems, necessitating the development of new functionalized polymers with reduced hysteresis for improved tire performance.

Innovation Solution

A method involving the polymerization of conjugated diene monomers using coordination catalysts or anionic initiators to create reactive polymers, which are then functionalized with protected oxime compounds containing a cyano group, resulting in polymers with reduced hysteresis suitable for tire components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of energy

If functionalized polymers are used to reduce hysteresis, then rolling resistance is reduced, but the effectiveness is unpredictable with existing functional groups

Engineering Contradiction:
Improvehysteresis lossVSAvoidpredictability of functional group effectiveness
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent introduces a new class of functional groups (protected oxime compounds containing cyano groups) with specific chemical parameters - the combination of oxime, cyano, and protected functionalities creates a novel chemical structure that systematically reduces hysteresis through multiple interaction mechanisms with filler particles and polymer chains

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The functionalized polymer represents a composite system combining the polymer backbone with multiple functional moieties (oxime, cyano, protected groups) that work synergistically to reduce hysteresis through simultaneous interactions with filler particles and polymer chain ends

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If new functionalized polymers are developed to reduce hysteresis, then tire performance is improved, but the manufacturing process becomes more complex

Engineering Contradiction:
Improvehysteresis lossVSAvoidpolymerization process complexity
Core Design Contradiction:
Loss of energyVSDevice complexity

Solution Approach 1:

The protected oxime compound is pre-synthesized with the cyano group and protecting group in advance, allowing the actual functionalization to occur in a single straightforward step during or after polymerization, rather than requiring multiple sequential modification steps

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The protecting group serves as an intermediary that allows the oxime functionality to be introduced in a controlled manner, preventing unwanted side reactions during polymerization while enabling subsequent deprotection to reveal the active functional group

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

The functionalized polymers demonstrate advantageously low hysteresis, enhancing tire performance by reducing rolling resistance and improving tensile properties, abrasion resistance, and fatigue resistance.

Implementation Method 1

polymerizing conjugated diene monomer, and optionally monomer copolymerizable therewith, along with either a coordination catalyst or an anionic initiator to form a reactive polymer

Methodology Applied
Scientific EffectPolymerization:

Implementation Method 2

reacting the reactive polymer with a protected oxime compound containing a cyano group

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP3143055B1Polymers functionalized with protected oxime compounds containing a cyano group
Publication Date: 2019.09.04 BRIDGESTONE CORP
  • EP3143055B1 patent drawingFigure 1
  • EP3143055B1 patent drawing
  • EP3143055B1 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 a protected oxime compound containing a cyano group.