Polymer-Bonded Perylene Inks for Document Security

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Solution Overview

Problem

Perylene, terrylene, and quaterrylene compounds have low solubility and dispersibility in liquid media, limiting their suitability as colorants in printing inks, which hinders the ability to distinguish authentic from counterfeit products and secure documents.

Innovation Solution

Polymer-bonded polycyclic aromatic hydrocarbon compounds with a perylene, terrylene, or quaterrylene moiety and nitrogen-containing heterocycloaliphatic substituents are developed, enhancing solubility and dispersibility in liquid media, specifically in printing inks, by forming a polymer-bonded structure with a polymeric moiety and nitrogen-containing heterocycloaliphatic groups.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If perylene, terrylene, or quaterrylene compounds are used as colorants in printing inks, then the ability to distinguish authentic from counterfeit products is improved, but the solubility and dispersibility in liquid media deteriorates

Engineering Contradiction:
Improveauthentication capabilityVSAvoidsolubility and dispersibility
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies composite materials by combining perylene, terrylene, or quaterrylene compounds with polymers to form polymer-bonded compounds. This composite structure maintains the fluorescent properties of the original compounds for authentication while the polymer component provides solubility and dispersibility in liquid ink media, thus resolving the technical contradiction between authentication capability and ease of manufacture

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent changes the chemical and physical parameters of the perylene, terrylene, or quaterrylene compounds by bonding them to polymer chains. This parameter change transforms the compounds from having poor solubility to having improved solubility and dispersibility, while preserving the optical properties necessary for authentication purposes

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 polymer-bonded compounds improve the solubility and dispersibility of perylene, terrylene, and quaterrylene inks, enabling better differentiation of authentic from counterfeit products and enhancing document security through improved optical properties.

Implementation Method 1

A class of compounds which is suitable for use in, e.g., printing inks for marking purposes are compounds having a perylene, terrylene or quaterrylene skeleton. Perylene, terrylene and quaterrylene display fluorescence

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP2776519B1Polymer-bonded polycyclic aromatic hydrocarbons having nitrogen containing substituents
Publication Date: 2016.06.22 SICPA HOLDING SA
  • EP2776519B1 patent drawing
  • EP2776519B1 patent drawing
  • EP2776519B1 patent drawing

AI summary

The invention concerns a polymer-bonded polycyclic aromatic hydrocarbon compound of general formula (1): (P—O) x —Q—(Y) w (1) wherein P represents a polymeric moiety having at least three repeating units which comprise an optionally substituted phenyl ring; Q represents a perylene, quaterrylene or terrylene moiety; Y is selected from (i) halogen and(ii) optionally substituted N-heterocycloaliphatic groups having from 3 to about 8 ring members which are bonded to Q through an N atom, provided that at least one Y represents(ii); x represents an integer of from 1 to 4; w represents an integer of from 1 to 4. The invention further concerns a process for making such a compound, and the use thereof in a printing ink composition, which can be used in particular for making marking or security features.