Functionalized Polydienes with Imide Compounds for Low Hysteresis

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Solution Overview

Problem

Current functionalized polymers used in tire manufacturing exhibit high cold flow due to their linear backbone structure, which complicates storage and processing, and their effectiveness in reducing hysteresis is unpredictable, making it challenging to develop polymers with both low hysteresis and reduced cold flow.

Innovation Solution

A method involving the polymerization of conjugated diene monomers using a lanthanide-based catalyst system, followed by functionalization with an imide compound containing a protected amino group, to produce cis-1,4-polydienes and poly(styrene-co-butadiene) with improved cold-flow resistance and reduced hysteresis.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If cis-1,4-polydienes are prepared with lanthanide-based catalysts to achieve better tensile properties and lower hysteresis, then the polymers exhibit high cold flow which causes problems during storage and transport

Engineering Contradiction:
Improvetensile properties and hysteresisVSAvoidcold flow resistance
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent extracts the problematic linear backbone structure characteristic of lanthanide-based catalyst polymers by introducing branched structures through functionalization with imide compounds. This removes the cold flow issue while preserving the beneficial tensile properties and hysteresis characteristics.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent creates a composite structure by functionalizing the polydiene backbone with imide compound side chains. This composite approach combines the mechanical advantages of cis-1,4-polydienes with the structural benefits of branched architectures, achieving both low hysteresis and reduced cold flow.

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If functionalized polymers are used to reduce hysteresis of rubber vulcanizates, then the functional group may reduce filler agglomeration, but whether a particular functional group can reduce hysteresis is often unpredictable

Engineering Contradiction:
ImprovehysteresisVSAvoidpredictability of functional group effectiveness
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent systematically varies parameters of the imide compound functional groups (such as the nature of R1, R2, and R3 substituents) to optimize hysteresis reduction. By establishing structure-property relationships, the patent makes the effectiveness of functional groups predictable rather than random.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The imide compound functional groups act as intermediaries between the polydiene backbone and filler particles. These intermediary groups mediate the interaction with fillers in a controlled manner, providing predictable hysteresis reduction through their specific chemical structure and properties.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Adaptability or versatility

If polymers are prepared with anionic initiators to achieve living characteristics, then the polymer chains possess living ends capable of reacting with functionalizing agents, but the polymers still exhibit high cold flow without coupled or branched structures

Engineering Contradiction:
Improveliving characteristics for further reactionVSAvoidcold flow
Core Design Contradiction:
Adaptability or versatilityVSEase of operation

Solution Approach 1:

The patent performs preliminary functionalization during or immediately after polymerization while the living ends are still active. This preliminary action introduces branched structures before the polymers are processed further, permanently eliminating cold flow issues while preserving the ability to undergo additional reactions if needed.

Inventive Principle:
Principle #10Preliminary action

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 resulting functionalized polymers demonstrate enhanced cold-flow resistance and low hysteresis, making them suitable for tire components with improved mechanical properties and processing ease.

Implementation Method 1

Lanthanide-based catalyst systems are known to be useful for polymerizing conjugated diene monomers to form polydienes having a high content of cis-1,4 linkage

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a reactive polymer is prepared by polymerizing conjugated diene monomer and optionally monomer copolymerizable therewith, and the reactive polymer is functionalized by reaction with an imide compound containing a protected amino group

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentEP2307461B1Polymers functionalized with imide compounds containing a protected amino group
Publication Date: 2017.02.08 BRIDGESTONE CORP
  • EP2307461B1 patent drawing
  • EP2307461B1 patent drawing

AI summary

A method for preparing a functionalized polymer, the method comprising the steps of preparing a reactive polymer and reacting the reactive polymer with an imide compound containing a protected amino group.