Esterified Aromatic Polyphenol Derivative for Rubber Reinforcement

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Solution Overview

Problem

Conventional rubber compositions used in tires face issues with premature crosslinking and degradation of mechanical properties due to high sulfur content and reinforcing fillers, leading to reduced vulcanization efficiency and increased rolling resistance, while the use of methylene acceptor/donor systems generates formaldehyde, a harmful compound.

Innovation Solution

The use of an aromatic polyphenol derivative with specific structural features, which reacts with an aldehyde to form a phenol-aldehyde resin in situ, delaying crosslinking and maintaining stiffness at high temperatures, thus avoiding premature crosslinking and formaldehyde production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If a concentrated vulcanization system with high sulfur content is used to obtain high stiffness, then the stiffness of the rubber composition is improved, but the uncured ageing is detrimentally affected with sulfur migration to the surface and blooming

Engineering Contradiction:
ImprovestiffnessVSAvoiduncured ageing stability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent replaces the conventional sulfur-based vulcanization system with an alternative crosslinking system using phenolic resin and hexamethylenetetramine (HMTA). This fundamental parameter change in the crosslinking mechanism eliminates sulfur migration and blooming while maintaining the desired stiffness through the phenol-aldehyde resin reinforcement.

Inventive Principle:
Principle #35Parameter changes

2Strength

If a concentrated vulcanization system is used to obtain high stiffness, then the stiffness is improved, but the delay phase during vulcanization is reduced leading to premature curing

Engineering Contradiction:
ImprovestiffnessVSAvoiddelay phase duration
Core Design Contradiction:
StrengthVSLoss of time

Solution Approach 1:

The phenolic resin is pre-condensed before incorporation into the rubber composition, creating a reservoir of reactive groups that will crosslink during vulcanization. This preliminary preparation allows for controlled crosslinking kinetics with an adequate delay phase, preventing premature curing while ensuring proper vulcanization timing.

Inventive Principle:
Principle #10Preliminary action

3Strength

If the content of reinforcing filler is increased to obtain high stiffness, then the stiffness is improved, but the hysteresis properties deteriorate leading to increased rolling resistance

Engineering Contradiction:
ImprovestiffnessVSAvoidrolling resistance
Core Design Contradiction:
StrengthVSLoss of energy

Solution Approach 1:

The patent creates a composite reinforcement system where phenol-aldehyde resin forms a three-dimensional network that integrates with both the filler and elastomer matrices. This composite approach provides stiffness enhancement through the resin network rather than relying solely on increased filler content, thereby maintaining better hysteresis and rolling resistance properties.

Inventive Principle:
Principle #40Composite materials

4Strength

If conventional phenolic resin with HMT or H3M is used as methylene acceptor/donor system to obtain high stiffness, then the stiffness is improved, but formaldehyde is produced during vulcanization

Engineering Contradiction:
ImprovestiffnessVSAvoidformaldehyde production
Core Design Contradiction:
StrengthVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the phenolic resin structure by replacing the conventional phenol groups with esterified aromatic polyphenol derivatives. This extraction of the harmful formaldehyde-generating moiety while retaining the reinforcing functionality eliminates formaldehyde production during vulcanization while maintaining the desired stiffness enhancement.

Inventive Principle:
Principle #2Taking out (Extraction)

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 enhances the stiffness and temperature resistance of rubber compositions while eliminating formaldehyde, improving vulcanization efficiency and reducing environmental impact.

Implementation Method 1

The terms 'methylene acceptor' and 'methylene donor' are well known to those skilled in the art and are widely used to denote compounds capable of reacting together to generate, by condensation, a three-dimensional reinforcing resin

Methodology Applied
Scientific EffectCondensation reaction:

Implementation Method 2

The methylene acceptor is combined with a hardener, capable of crosslinking or curing it, also commonly known as a methylene donor

Methodology Applied
Scientific EffectCrosslinking:

Data Source

PatentUS10711132B2Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition
Publication Date: 2020.07.14 MICHELIN & CO (CIE GEN DES ESTAB MICHELIN)
  • US10711132B2 patent drawing
  • US10711132B2 patent drawing
  • US10711132B2 patent drawing

AI summary

An aromatic polyphenol derivative which comprises at least one aromatic ring bearing at least two —O—Z groups in the meta position relative to one another, the two positions ortho to at least one of the —O—Z groups being unsubstituted, is used for the manufacture of a phenol-aldehyde resin for reinforcing a rubber composition. Each —O—Z group represents an —O—((C═O)(R1)) group with R1 representing a hydrocarbon-based radical or a substituted hydrocarbon-based radical.