Spiro Bisphosphite Antioxidant Thermal Stability

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Solution Overview

Problem

Conventional phosphorus-based antioxidants used in polymer materials face challenges with low thermal stability and hydrolytic stability, leading to degradation and processing issues during high-temperature processing and exposure to moisture, which affects the lifespan and properties of polymer materials.

Innovation Solution

A spiro bisphosphite compound with aliphatic C4-C9 alkyl groups at the para positions of benzene rings is developed, offering improved thermal stability above 320°C and enhanced hydrolytic stability, along with better solubility in organic solvents, suitable for high-temperature processing of thermoplastic polymers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional phosphorus-based antioxidants are used, then antioxidation efficiency is improved, but thermal stability deteriorates

Engineering Contradiction:
Improveantioxidation efficiencyVSAvoidthermal stability
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent modifies the molecular structure of phosphorus-based antioxidants by changing the substituents at para positions of benzene rings from conventional groups to specific C4-C9 alkyl groups. This parameter change in molecular structure results in a new compound with both high antioxidation efficiency and exceptional thermal stability (TGA temperature above 320°C), resolving the contradiction between antioxidation efficiency and thermal stability.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If conventional phosphorus-based antioxidants are used, then antioxidation efficiency is improved, but hydrolytic stability deteriorates

Engineering Contradiction:
Improveantioxidation efficiencyVSAvoidhydrolytic stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters of the phosphorus-based antioxidant by introducing specific C4-C9 alkyl groups at the para positions of benzene rings. This structural modification creates a compound that maintains high antioxidation efficiency while achieving excellent hydrolytic stability, preventing hydrolysis-induced discoloration and caking.

Inventive Principle:
Principle #35Parameter changes

3Temperature

If high thermal stability is achieved, then processing temperature resistance is improved, but solubility in organic solvents deteriorates

Engineering Contradiction:
Improvethermal stabilityVSAvoidsolubility in organic solvents
Core Design Contradiction:
TemperatureVSEase of manufacture

Solution Approach 1:

The patent applies local quality modification by introducing specific C4-C9 alkyl groups (such as tert-butyl, cyclohexyl, or heptyl groups) at the para positions of the benzene rings. These localized structural changes provide a balance between thermal stability and solubility, as the alkyl groups contribute to thermal resistance while maintaining appropriate solubility in organic solvents for processing.

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 compound effectively inhibits polymer degradation, maintaining high antioxidation efficiency and preventing discoloration, caking, and deliquescence, ensuring stable quality and prolonged lifespan of polymer materials during processing and storage.

Implementation Method 1

Primary antioxidants scavenge free radicals while secondary antioxidants decompose hydrogen peroxides

Methodology Applied
Scientific EffectFree radical scavenging: Oxidation

Implementation Method 2

Secondary antioxidants include phosphorus based compounds, sulfur based compounds, and amine based compounds

Methodology Applied
Scientific EffectHydroperoxide decomposition: Decomposition (biological)

Implementation Method 3

Conventional phosphorus based antioxidants tend to hydrolyze in humid environment or when in contact with moisture

Methodology Applied
Scientific EffectHydrolytic stability: Hydrolysis

Implementation Method 4

Thermal stability is crucial for thermoplastic polymer materials as well, because during their service life, thermoplastic polymer materials must be processed at elevated temperature

Methodology Applied
Scientific EffectThermal stability: Thermal Expansion

Data Source

PatentEP2944644B1Spiro bisphosphite based compound and uses of the same
Publication Date: 2017.11.01 CHITEC TECH
  • EP2944644B1 patent drawing
  • EP2944644B1 patent drawing
  • EP2944644B1 patent drawing

AI summary

A spiro bisphosphite based compound and its uses are disclosed. The compound is represented by the following Formula VII': wherein R is C4-C9 alkyl.