Rubber Antiozonant Composition That Avoids Toxic 6PPDQ Formation

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Solution Overview

Problem

Existing antiozonants, such as 6PPD, form toxic compounds like 6PPDQ when exposed to ozone, which can contaminate waterways and harm aquatic life.

Innovation Solution

Development of new antiozonants with the formula (I), where X is O, S, or N, and R is a variety of moieties, which do not form 6PPDQ when exposed to ozone, thereby reducing environmental toxicity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If 6PPD is used as an antiozonant, then ozone protection is provided, but toxic 6PPDQ is formed which contaminates waterways and harms aquatic life

Engineering Contradiction:
Improveozone protectionVSAvoidtoxicity to aquatic life
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of the antiozonant by changing the parameters of the diamine molecule - specifically using substituted p-phenylenediamines with different alkyl groups at the N1 and N4 positions. This structural parameter change allows the antiozonant to provide ozone protection without forming the toxic quinone byproduct 6PPDQ, thus resolving the contradiction between effectiveness and environmental harm

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite antiozonant systems combining multiple diamine components with specific structural features. These composite materials work synergistically to provide robust ozone protection while the specific molecular structures prevent formation of highly toxic quinone products, addressing both the protection requirement and environmental safety concern

Inventive Principle:
Principle #40Composite materials

2Duration of action of stationary object

If conventional antiozonants are used, then surface crack prevention is achieved, but environmental contamination occurs through stormwater runoff

Engineering Contradiction:
Improveservice life of rubber articleVSAvoidenvironmental contamination
Core Design Contradiction:
Duration of action of stationary objectVSObject-affected harmful factors

Solution Approach 1:

The patent converts the potential harm of quinone formation into a benefit by designing antiozonants that follow a different degradation pathway. Instead of forming toxic quinones like 6PPDQ, the new antiozonants form less harmful oxidation products that do not pose significant environmental risks, thus transforming what would be a harmful byproduct issue into a environmentally safe solution while maintaining crack protection

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

By changing the substituent parameters on the p-phenylenediamine core structure - specifically using bulkier or differently positioned alkyl groups - the patent alters the oxidation pathway of the antiozonant. This parameter modification ensures that when the antiozonant degrades through stormwater runoff, it does not generate toxic quinones but rather benign products, resolving the environmental contamination issue while preserving the extended service life benefit

Inventive Principle:
Principle #35Parameter changes

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 new antiozonants effectively prevent the formation of toxic 6PPDQ, thereby enhancing the environmental safety of rubber compositions and extending the useful lifetime of rubber articles like tires.

Implementation Method 1

6PPD is known to interact with ozone to form N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone or 6PPDQ

Methodology Applied
Scientific EffectOzone interaction: Ozone

Implementation Method 2

Ozone can attack the surface of rubber, thereby resulting in surface cracks

Methodology Applied
Scientific EffectAntiozonant mechanism: Oxidation

Data Source

PatentUS20250188252A1Antiozonant and associated rubber composition and rubber article
Publication Date: 2025.06.12 THE GOODYEAR TIRE & RUBBER CO
  • US20250188252A1 patent drawing
  • US20250188252A1 patent drawing
  • US20250188252A1 patent drawing

AI summary

An antiozonant of formula (I):wherein X is selected from the group consisting of O, S, and N; and wherein R is selected from the group consisting of hydrogen, an alkyl moiety, a cycloalkyl moiety, an aryl moiety, an amine moiety, an amide moiety, an alcohol moiety, an aldehyde moiety, a ketone moiety, a carboxylic acid moiety, an ether moiety, an ester moiety, and a thiol moiety. A rubber composition contains the antiozonant, a diene elastomer; a reinforcing filler; a sulfur-based curing agent; and an accelerator for the curing agent.