Methine Dyes for Polyamide Coloring with Enhanced Light Fastness

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Solution Overview

Problem

Current yellow dyes for coloring plastics, particularly polyamides, lack sufficient light and heat resistance, failing to meet the high technical requirements for bulk dyeing due to their inadequate fastness and thermal stability.

Innovation Solution

Development of new methine dyes with the formula (I), characterized by specific substituents, which provide improved light fastness and thermal stability, allowing for yellow coloring of plastics with enhanced properties when used in bulk coloring processes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional yellow dyes are used for bulk coloring of polyamides, then the coloring process is simple and cost-effective, but the light fastness and thermal stability are insufficient

Engineering Contradiction:
Improvelight fastness and thermal stabilityVSAvoiddye molecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure of methine dyes through specific substitutions: introducing electron-withdrawing groups (Cl, F, CF3) at defined positions on the indole and benzene rings, and optimizing the methine bridge composition. These structural parameter changes enhance the dye's resistance to light and heat while maintaining its coloring function, directly resolving the contradiction between reliability and structural complexity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining indole rings, benzene rings with specific substituents, and methine bridges. This composite structure integrates multiple functional elements that work synergistically: the substituted aromatic rings provide thermal stability, the methine bridge enables coloration, and the overall configuration ensures light fastness. This composite approach allows the dye to meet high reliability requirements without requiring overly complex synthesis processes.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If dyes with higher thermal stability are developed, then the color fastness under processing conditions improves, but the synthesis complexity and production cost increase

Engineering Contradiction:
Improvethermal stabilityVSAvoidsynthesis process simplicity
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent applies local quality by introducing specific substituents at precise positions on the molecular structure rather than uniformly modifying the entire molecule. For example, chlorine or fluorine atoms are placed at specific positions (2, 4, 5, 6 on indole ring; 2, 4, 5, 6 on benzene ring) to locally enhance thermal stability where it is most needed, while keeping other parts of the molecule simple and easy to synthesize. This localized modification approach improves thermal stability without proportionally increasing synthesis complexity.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The dye molecule is segmented into distinct functional units: the indole core, the benzene ring with substituents, and the methine bridge. Each segment can be independently optimized and synthesized, then assembled into the final structure. This segmentation allows for systematic development of thermal stability through substituent selection while maintaining ease of manufacture through modular synthesis approaches.

Inventive Principle:
Principle #1Segmentation

3Strength

If conventional yellow colorants are used, then the processing is straightforward, but the color strength and vibrancy are insufficient

Engineering Contradiction:
Improvecolor strengthVSAvoiddye concentration required
Core Design Contradiction:
StrengthVSQuantity of substance

Solution Approach 1:

The patent enhances color strength by changing the molecular parameters of the dye, specifically through the introduction of extended conjugation in the methine bridge and the addition of electron-withdrawing substituents. These parameter changes increase the molar absorptivity of the dye, allowing for stronger coloration at lower concentrations. This directly addresses the contradiction by improving color strength without requiring increased quantities of substance.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3247749B1Yellow methine dyes
Publication Date: 2019.06.26 LANXESS DEUTSCHLAND GMBH
  • EP3247749B1 patent drawing
  • EP3247749B1 patent drawing
  • EP3247749B1 patent drawing

AI summary

The present invention relates to novel methine dyes, methods for producing same and the use thereof for dyeing plastics, in particular polyamides, so as to obtain yellow colourings with improved light fastness and improved thermostability.