Antidegradant Compounds for Rubber Degradation Resistance

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Solution Overview

Problem

Current antidegradants for vulcanized rubber articles and elastomeric formulations face challenges in providing long-term efficacy against oxidative degradation, ozonative degradation, and mechanical fatigue, particularly at lower concentrations and over extended periods, while maintaining compatibility with other additives and desirable material characteristics.

Innovation Solution

Development of antidegradant compounds represented by formula I, derived from the reaction of p-phenylenediamine with alpha-hydroxy carbonyl compounds, which are then reduced or hydrogenated to produce enediamines, offering enhanced resistance to crack propagation and degradation mechanisms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antidegradants are used in vulcanized rubber articles, then degradation protection is provided, but efficacy duration is limited and requires higher concentrations

Engineering Contradiction:
Improvedegradation protectionVSAvoidefficacy duration
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent modifies the chemical structure of antidegradant compounds by introducing specific molecular configurations and functional groups that enhance their stability and longevity. This structural parameter change allows the antidegradants to maintain protective efficacy for extended periods without requiring higher concentrations, directly resolving the contradiction between protection reliability and duration of action.

Inventive Principle:
Principle #35Parameter changes

2Duration of action of stationary object

If antidegradant concentration is increased to extend efficacy period, then degradation resistance improves, but material compatibility and desirable characteristics are compromised

Engineering Contradiction:
Improveefficacy periodVSAvoidadditive compatibility
Core Design Contradiction:
Duration of action of stationary objectVSAdaptability or versatility

Solution Approach 1:

The patent achieves extended efficacy periods through optimized molecular structures and functional group configurations that enhance the antidegradant's intrinsic stability. This allows effective protection at lower concentrations, thereby maintaining compatibility with other additives and preserving desirable material characteristics without the need for high dosages.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional antidegradants are used, then oxidative degradation is inhibited, but antifatigue performance and crack propagation resistance are insufficient

Engineering Contradiction:
Improveoxidative degradation inhibitionVSAvoidfatigue resistance
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The patent designs antidegradant compounds with multi-functional capabilities that simultaneously provide oxidative degradation inhibition, ozonative degradation protection, and fatigue resistance. The molecular structure incorporates multiple active sites and functional groups that can address different degradation mechanisms concurrently, thereby resolving the contradiction between oxidative protection and fatigue performance.

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

Solution Approach 2:

The patent employs composite antidegradant systems combining multiple functional components or synergistic molecular structures that offer combined protection against oxidation, ozone, and mechanical fatigue. This composite approach enables the material to achieve superior overall performance across multiple degradation modes without compromising any single protective function.

Inventive Principle:
Principle #40Composite materials

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 compounds demonstrate superior antidegradant and antifatigue performance, providing improved resistance to oxidative, ozonative degradation, and mechanical fatigue in vulcanized rubber articles, particularly in tire components, with extended efficacy periods and reduced concentrations.

Implementation Method 1

demonstrating antidegradant efficacy are well known in the art. For example, U.S. Pat. No. 8,987,515 discloses an aromatic polyamine useful in inhibiting oxidative degradation

Methodology Applied
Scientific EffectAntioxidant: Oxidation

Implementation Method 2

Articles formed from general purpose elastomers such as natural rubber, in particular tires, are especially prone to degradation from both oxygen and ozone

Methodology Applied
Scientific EffectAntiozonant: Ozone

Implementation Method 3

antifatigue agent efficacies and accordingly are particularly useful in imparting resistance to crack propagation, degradation and the many manifestations thereof

Methodology Applied
Scientific EffectFatigue resistance: Fatigue

Data Source

PatentUS10160718B2Methods of making compounds having antidegradant and antifatigue efficacy
Publication Date: 2018.12.25 FLEXSYS IP HOLDINGS LLC
  • US10160718B2 patent drawing
  • US10160718B2 patent drawing
  • US10160718B2 patent drawing

AI summary

A method of making antidegradant compounds is disclosed, in which a p-phenylenediamine is reacted with an alpha-hydroxy carbonyl compound to thereby obtain an enediamine, which is reduced to thereby obtain a mixture comprising the antidegradant compound.