Poly(oxyalkylene) Perylene Bisimide Solubility

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Perylene bisimide dyes have limited solubility in common organic solvents, restricting their application as fluorescent security taggants despite their high fluorescence quantum yield and photostability.

Innovation Solution

The attachment of poly(oxyalkylene) substituents to perylene-based compounds, such as perylene poly(oxyalkylene) bisimides and tetraamides, enhances their solubility in organic solvents, allowing for their use in high-concentration ink and coating formulations with improved light fastness and fluorescence properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If perylene bisimide dyes are used as fluorescent security taggants, then high fluorescence quantum yield and photostability are achieved, but solubility in common organic solvents is limited

Engineering Contradiction:

Improvefluorescence quantum yield and photostabilityVSAvoidsolubility in organic solvents

Core Design Contradiction:

ReliabilityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of perylene bisimide dyes through attachment of poly(oxyalkylene) substituents. This structural modification changes the solubility parameters of the dye molecules, enabling them to dissolve in common organic solvents at high concentrations while preserving their fluorescent properties. The poly(oxyalkylene) chains increase the polarity and flexibility of the molecules, improving compatibility with various solvent systems.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite materials by combining perylene bisimide chromophores with poly(oxyalkylene) side chains. This composite structure integrates the fluorescent core with solubilizing peripheral groups, achieving a material that possesses both high fluorescence quantum yield and improved solubility. The composite approach allows the dye to function effectively in ink formulations for security taggant applications.

Inventive Principle:

Principle #40Composite materials

2Reliability

If perylene bisimide dyes are used in security taggant applications, then high fluorescence properties are achieved, but solubility restrictions prevent use in high-concentration ink formulations

Engineering Contradiction:

Improvefluorescence propertiesVSAvoidformulation in ink and coating compositions

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the physical and chemical parameters of the perylene bisimide dyes by introducing poly(oxyalkylene) substituents. This changes the solubility characteristics and molecular interactions, allowing the dyes to be formulated at high concentrations in various ink types including water-based and solvent-based systems. The parameter change enables practical manufacturing of security taggant products.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The poly(oxyalkylene) substituents act as intermediary groups that mediate between the hydrophobic perylene core and the polar solvent environment. These intermediary chains facilitate interaction between the dye and solvent molecules, enabling solubility and proper formulation behavior without compromising the fluorescent properties of the core structure.

Inventive Principle:

Principle #24Intermediary (Mediator)

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 resulting compounds exhibit excellent solubility and fluorescence, making them suitable for demanding applications like water-based and solvent-based inks, and provide stable, high-fluorescence security taggants for various substrates.

Implementation Method 1

The attachment of poly(oxyalkylene) substituents to perylene-based compounds, such as perylene poly(oxyalkylene) bisimides and tetraamides, enhances their solubility in organic solvents

Methodology Applied

Scientific EffectSolvation: Solvation

Implementation Method 2

3,4,9,10-Perylene tetracarboxylic acid bisimide based colorants... exhibit desirable migratory properties... Patents DE 1130099 and GB 967178 first disclosed the potential for using perylenes as fluorescent dyes with high fluorescence quantum yield and photostability

Methodology Applied

Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP2104699B1Poly(oxyalkylene)ated colorants and their use as fluorescent security taggants

Publication Date: 2015.10.14 SUN CHEMICAL CORP

Figure 1

AI summary

Certain poly(oxyalkylene) colorants are disclosed along with method of preparation thereof. A method of using these colorants as fluorescent security taggants is also disclosed.