N-Protected Hydantoin Functionalized Polymers for Tire Hysteresis

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Solution Overview

Problem

Current rubber vulcanizates used in tire manufacturing exhibit high cold flow and unpredictable hysteresis reduction due to their linear backbone structure, which complicates storage and processing, and existing functionalized polymers are not consistently effective in reducing hysteresis across different polymer types.

Innovation Solution

A method involving the polymerization of conjugated diene monomers using lanthanide-based catalyst systems to produce reactive cis-1,4-polydienes, which are then functionalized with N-protected hydantoin compounds to create polymers 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, higher abrasion resistance, lower hysteresis, and better fatigue resistance, then the polymers exhibit high cold flow which causes problems during storage and transport and hinders the use of automatic feeding equipment

Engineering Contradiction:
Improvetensile properties, abrasion resistance, hysteresis, fatigue resistanceVSAvoidcold flow resistance, storage and transport handling, automatic feeding equipment compatibility
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the polymer through functionalization with N-protected hydantoin compounds. This changes the physical and chemical parameters of the polymer, specifically reducing cold flow while maintaining the beneficial mechanical properties achieved through lanthanide-based catalysis. The functionalization transforms the linear backbone structure into a more complex structure with improved storage stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite materials by combining cis-1,4-polydienes with N-protected hydantoin functional groups. This composite structure integrates the excellent mechanical properties of lanthanide-catalyzed polydienes with the cold flow resistance provided by the hydantoin functionalization, achieving a material that satisfies both performance and processing requirements.

Inventive Principle:
Principle #40Composite materials

2Loss of energy

If functionalized polymers are employed to reduce the hysteresis of rubber vulcanizates, then the functional group may reduce the number of free polymer chain ends via interaction with filler particles, but whether a particular functional group can reduce hysteresis is often unpredictable

Engineering Contradiction:
ImprovehysteresisVSAvoidpredictability of hysteresis reduction
Core Design Contradiction:
Loss of energyVSReliability

Solution Approach 1:

The patent uses N-protected hydantoin compounds as intermediary functional groups that mediate between the polymer chain ends and filler particles. These functional groups specifically interact with filler particles to reduce free chain ends and thereby reduce hysteresis in a predictable and consistent manner across different polymer types.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent systematically changes the functional group parameter by selecting N-protected hydantoin compounds, which have been found to provide consistent and predictable hysteresis reduction. This parameter selection is based on the specific chemical properties of hydantoin groups that enable reliable interaction with filler particles.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If functionalized polymers are prepared by post-polymerization treatment of reactive polymers with certain functionalizing agents, then functionalization can be achieved, but whether a reactive polymer can be functionalized by treatment with a particular functionalizing agent can be unpredictable

Engineering Contradiction:
Improvefunctionalization capabilityVSAvoidpredictability of functionalization success
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent demonstrates universality by showing that N-protected hydantoin compounds can successfully functionalize multiple types of reactive polymers, including cis-1,4-polydienes and other polymers with reactive chain ends. This multi-functional capability makes the functionalization process predictable and reliable across different polymer systems.

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

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 high cis-1,4 linkage contents

Methodology Applied
Scientific EffectCoordination polymerization: Catalysis

Implementation Method 2

reacting the reactive polymer with an N-protected hydantoin compound

Methodology Applied
Scientific EffectChemical bonding: Chemical Bonding

Data Source

PatentUS10899718B2Polymers functionalized with N-protected hydantoin compounds
Publication Date: 2021.01.26 BRIDGESTONE CORP
  • US10899718B2 patent drawing
  • US10899718B2 patent drawing
  • US10899718B2 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 N-protected hydantoin compound.