Polyalkyl P-Phenylenediamine Antidegradant for Thermal and UV Aging

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Solution Overview

Problem

Current p-phenylenediamine antidegradants used in rubber products, such as 6PPD, require expensive catalysts, generate metal bromide salts, and have low conversion rates, making them unsuitable for industrial production, and there is a need for a novel structure with improved thermal and ultraviolet aging resistance.

Innovation Solution

A polyalkyl p-phenylenediamine antidegradant with a specific structure is synthesized using a green and environmentally friendly preparation method involving condensation and reductive alkylation reactions with catalysts like Raney nickel and supported metal catalysts, avoiding the use of bromide and reducing waste generation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional C-N coupling reaction with bromide and precious metal catalysts is used, then p-phenylenediamine antidegradant can be synthesized, but the conversion rate and yield are low and expensive metal bromide salts waste is generated

Engineering Contradiction:
Improveantidegradant performanceVSAvoidmetal bromide salts waste
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent removes the harmful bromide component from the synthesis pathway by using direct condensation of aniline derivatives with nitrobenzene instead of C-N coupling with bromonitrobenzene. This extraction of the harmful element eliminates metal bromide salts waste while maintaining the ability to synthesize the desired antidegradant product.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces expensive precious metal catalysts (Pd, Pt) with inexpensive iron powder as the catalyst. Iron is abundant, cheap, and can be easily disposed of or regenerated, eliminating the need for costly precious metals while maintaining catalytic functionality for the reduction step.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Ease of manufacture

If expensive precious metal catalysts are used, then the reaction can proceed, but the production cost increases significantly

Engineering Contradiction:
Improvereaction feasibilityVSAvoidproduction cost
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent substitutes expensive precious metal catalysts with inexpensive iron powder. Iron is abundant, low-cost, and sufficient for the reaction requirements, dramatically reducing production costs while maintaining the ability to catalyze the reduction of nitro groups to amino groups.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the catalyst material parameter from precious metals to iron, and optimizes reaction conditions (temperature, pressure, solvent) to compensate and maintain effective catalysis. This parameter substitution achieves cost reduction without sacrificing reaction feasibility.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional antidegradant structures are used, then basic protection is provided, but thermal oxidative aging resistance and ultraviolet aging resistance are insufficient

Engineering Contradiction:
Improvebasic protectionVSAvoidthermal and UV aging
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent creates antidegradant molecules with composite structural features by introducing diverse substituents (alkyl groups at positions 2,6 and various groups at position 4) on the phenylenediamine core. This composite molecular structure provides enhanced protection against multiple degradation mechanisms including thermal oxidation and UV radiation simultaneously.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies different substituent types at different positions on the phenylenediamine molecule (alkyl groups at 2,6 positions, various groups at 4 position) to provide localized functional properties. This local differentiation of molecular structure enhances overall antidegradant performance against specific aging factors while maintaining basic protection.

Inventive Principle:
Principle #3Local quality

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 antidegradant provides enhanced thermal oxidative aging resistance and ultraviolet aging resistance to rubber products, with a preparation process that is environmentally friendly and cost-effective by eliminating the need for expensive catalysts and reducing waste.

Implementation Method 1

reacting aniline or its derivatives and nitrobenzene in condensation in the presence of a first catalyst to obtain an intermediate compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reducing the intermediate compound in the presence of H2 and a second catalyst to obtain a polyalkyl p-phenylenediamine antidegradant

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP4617257A1Polyalkyl p-phenylenediamine Anti-aging agent, and intermediate thereof and preparation method therefor
Publication Date: 2025.09.17 SENNICS CO LTD
  • EP4617257A1 patent drawing
  • EP4617257A1 patent drawing
  • EP4617257A1 patent drawing

AI summary

Provided is a polyalkyl p-phenylenediamine anti-aging agent having a structure as shown in formula I, and an intermediate thereof and a preparation method therefor. The polyalkyl p-phenylenediamine anti-aging agent has good thermo-oxidative aging resistance and ultraviolet aging resistance.