Phenoxyphenol Stabilizer for Polyolefin Oxidation Resistance

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Solution Overview

Problem

Organic materials such as thermoplastic resins deteriorate due to heat and oxygen exposure during processing and use, requiring effective stabilizers to enhance processing stability and oxidation resistance.

Innovation Solution

A compound represented by formula (I), where R1-R4 are independently t-butyl or t-pentyl groups, is used as a stabilizer for organic materials, specifically improving processing stability and oxidation resistance when mixed with thermoplastic resins like polyolefins, polyamides, or polycarbonates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional phenolic antioxidants are used to improve oxidation resistance, then oxidation resistance is improved, but processing stability during high-temperature processing deteriorates

Engineering Contradiction:
Improveoxidation resistanceVSAvoidprocessing stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The invention changes the chemical structure parameters of the antioxidant by introducing specific substituents (tert-butyl groups at positions 2,6 and t-butyl or t-pentyl groups at positions 2',6' of the phenoxyphenol core) to optimize both oxidation resistance and processing stability. This structural modification allows the compound to maintain stability at high processing temperatures while effectively preventing oxidation during use.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining features of both high-temperature stabilizers and phenolic antioxidants in a single molecule. The phenoxyphenol core provides antioxidant activity while the specific bulky substituents provide thermal stability, effectively combining multiple functions in one compound.

Inventive Principle:
Principle #40Composite materials

2Reliability

If stabilizer concentration is increased to improve stability, then oxidation resistance and processing stability are improved, but cost and potential negative effects on material properties worsen

Engineering Contradiction:
ImprovestabilityVSAvoidstabilizer concentration
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The optimized molecular structure achieves maximum stabilization efficiency at low concentrations by strategically placing electron-donating tert-butyl groups that enhance the antioxidant activity per molecule, reducing the total quantity needed while maintaining or improving performance.

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 compound effectively suppresses thermal and oxidative degradation, enhancing the stability and oxidation resistance of organic material compositions, particularly in polyethylene and polypropylene, while maintaining processability and economic viability.

Implementation Method 1

The compound (I) has a specific molecular structure with t-butyl and t-pentyl groups that create steric hindrance, preventing close approach of reactive species to vulnerable sites in the polymer chain

Methodology Applied
Scientific EffectSteric hindrance:

Implementation Method 2

The phenolic hydroxyl group in compound (I) acts as a radical scavenger, donating hydrogen atoms to terminate free radical chains that cause thermal and oxidative degradation

Methodology Applied
Scientific EffectRadical scavenging:

Implementation Method 3

The compound (I) intercepts peroxyl radicals (ROO•) formed during oxidation, converting them to stable hydroperoxides and phenoxyl radicals that do not propagate degradation

Methodology Applied
Scientific EffectPeroxyl radical interception:

Implementation Method 4

The compound facilitates decomposition of accumulated hydroperoxides into non-radical products, preventing their breakdown into highly reactive radicals that accelerate oxidation

Methodology Applied
Scientific EffectHydroperoxide decomposition:

Data Source

PatentEP3348541B1Stabilizer for organic materials
Publication Date: 2020.09.30 SUMITOMO CHEM CO LTD
  • EP3348541B1 patent drawing
  • EP3348541B1 patent drawing
  • EP3348541B1 patent drawing

AI summary

The present invention provides a compound represented by the formula (I): wherein R1 - R4 are each independently a t-butyl group or a t-pentyl group.