Methine Dyes for Polyamides with Thermal Stability

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Solution Overview

Problem

Current yellow colorants for plastics, particularly polyamides, lack sufficient thermal and light stability, and often compromise the mechanical properties of polymers, failing to meet the stringent requirements for bulk dyeing, especially when combined with glass fibers.

Innovation Solution

Development of new methine dyes with specific structural formulas that provide improved light fastness, thermal stability, and color strength, allowing for transparent or muted yellow to orange colorations in plastics, particularly polyamides, without negatively affecting mechanical properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If pigments are used for coloring plastics, then thermal stability is improved, but transparency deteriorates and mechanical properties worsen

Engineering Contradiction:
Improvethermal stabilityVSAvoidmechanical properties deterioration
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by transitioning from pigment form to soluble dye form, and by modifying the chemical structure of methine dyes through specific substituents (R1-R7 groups) to achieve both thermal stability and transparency. The dyes are designed with specific molecular parameters that allow them to remain stable at high processing temperatures while maintaining polymer mechanical properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite effect by combining multiple chemical structures within the methine dye framework, integrating electron-donating and electron-withdrawing groups to achieve a balanced performance profile that simultaneously provides thermal stability, transparency, and mechanical property preservation.

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If known yellow dyes are used for coloring polyamides, then coloration is achieved, but light fastness and thermal stability are insufficient

Engineering Contradiction:
Improvecoloration capabilityVSAvoidlight fastness and thermal stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of methine dyes through specific substituents (R1-R7 groups) to achieve both thermal stability and transparency. The dyes are designed with specific molecular parameters that allow them to remain stable at high processing temperatures while maintaining polymer mechanical properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs strong electron-withdrawing groups (such as nitro, cyano, and carbonyl groups) that act as strong oxidizing centers, enhancing the dye's resistance to oxidation during processing and application, thereby improving both light fastness and thermal stability.

Inventive Principle:
Principle #38Strong oxidants (Accelerated oxidation)

3Productivity

If processing temperature is increased for bulk dyeing of polyamides, then dyeing efficiency is improved, but colorant stability deteriorates

Engineering Contradiction:
Improvedyeing efficiencyVSAvoidcolorant stability
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of methine dyes through specific substituents (R1-R7 groups) to achieve both thermal stability and transparency. The dyes are designed with specific molecular parameters that allow them to remain stable at high processing temperatures while maintaining polymer mechanical properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies beforehand cushioning by incorporating stabilizing chemical groups into the dye structure prior to processing, which preemptively protect the colorant from degradation during high-temperature bulk dyeing operations, ensuring both efficiency and stability.

Inventive Principle:
Principle #11Beforehand cushioning (Prior cushioning)

Data Source

PatentEP3470467B1Methine dyes for coloring plastics
Publication Date: 2022.07.27 LANXESS DEUTSCHLAND GMBH
  • EP3470467B1 patent drawing
  • EP3470467B1 patent drawing
  • EP3470467B1 patent drawing

AI summary

The present invention relates to novel methine dyes, processes for their production, and their use for dyeing plastics, in particular polyamides, yielding yellow to orange colors with improved lightfastness and improved thermostability. The dye has the following formula (I):