ADAME Stabilization with 2,6-di-tert-butyl-4-methylphenol

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Solution Overview

Problem

N,N-dimethyl aminoethyl acrylate (ADAME) exhibits color instability over time, leading to yellowing and water coloring issues, requiring specific storage conditions, which complicates its handling and usage in industrial applications.

Innovation Solution

The introduction of 2,6-di-tert-butyl-4-methyl phenol at concentrations between 25 to 200 ppm during the purification process of ADAME stabilizes the compound against coloring, allowing for longer storage at higher temperatures without significant color change.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If ADAME is stored without specific temperature control and light protection, then storage and transport facilities are simplified, but the compound undergoes yellowing and color instability

Engineering Contradiction:
Improvestorage and transport convenienceVSAvoidcolor stability
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

A polymerization inhibitor (2,6-di-tert-butyl-4-methylphenol) is added to the ADAME composition before storage, in advance preventing the color instability and yellowing that would otherwise occur during storage and transport, thereby eliminating the need for stringent temperature and light control measures

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The polymerization inhibitor acts as an intermediary substance that mediates between the ADAME and environmental factors (light, heat, oxygen) that cause degradation, protecting the ADAME from direct harmful effects while allowing storage under relaxed conditions

Inventive Principle:
Principle #24Intermediary (Mediator)

2Stability of the object's composition

If ADAME is stored under specific temperature conditions below 5°C and protected from light, then color stability is maintained, but storage and transport facilities become complicated

Engineering Contradiction:
Improvecolor stabilityVSAvoidstorage and transport facility complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The inhibitor is incorporated into the ADAME composition during production, pre-establishing protection against color instability before the product enters storage and distribution channels, thereby eliminating the need for complex cold chain and light-protected storage infrastructure

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The addition of the polymerization inhibitor changes the chemical composition parameters of ADAME, fundamentally altering its stability characteristics and enabling storage at higher temperatures without light protection, thus simplifying storage facility requirements

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 stabilization of ADAME with 2,6-di-tert-butyl-4-methyl phenol results in a composition with less than 100 Apha coloring after storage at various temperatures for extended periods, enabling safe storage at room temperature and reducing the need for stringent storage conditions.

Implementation Method 1

2,6-di-tert-butyl-4-methylphenol made it possible to obtain an ADAME stabilized with respect to the color... The presence of both compounds is necessary to ensure ADAME's stabilization... adding at least one compound chosen from among those containing an amido group, phosphorous acid esters, phosphoric acid esters, and phosphines, and at least one substituted phenolic compound

Methodology Applied
Scientific EffectAntioxidant stabilization: Oxidation

Data Source

PatentEP3448834B1N,n-dimethylaminoethyl acrylate composition stabilized in respect of discoloring effects
Publication Date: 2023.03.15 ARKEMA FRANCE SA

AI summary

The invention relates to the use of 2,6-di-tert-butyl-4-methylphenol at a moiety of 25 to 200 ppm for stabilizing N,N-dimethylaminoethyl acrylate in respect of discoloring effects. The invention also relates to an N,N-dimethylaminoethyl acrylate stabilized in said manner and to a method for producing same.