Infrared Absorbing Dye for High-Contrast Lithographic Plates

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Solution Overview

Problem

Existing heat-sensitive lithographic printing plate precursors using infrared (IR) dyes suffer from low contrast in print-out images due to side-absorption in the visible wavelength range, which limits the visibility and differentiation of exposed areas before development.

Innovation Solution

Development of an IR-absorbing dye with a specific chemical structure that undergoes a transformation upon IR exposure, increasing light absorption in the visible wavelength range, thereby enhancing the contrast of print-out images by forming a stronger electron-donor or acceptor group, and potentially forming dimers or oligomers for improved performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If conventional IR dyes are used in heat-sensitive lithographic printing plate precursors, then the plate precursor can be exposed to IR radiation and form an image, but the print-out image shows low contrast due to side-absorption in the visible wavelength range

Engineering Contradiction:
Improvecontrast of print-out imageVSAvoidside-absorption in visible wavelength range
Core Design Contradiction:
Measurement precisionVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of the IR dye by introducing specific substituents (such as cyano groups, nitro groups, or carbonyl groups) at positions 5 and 6 of the indolenine ring. This structural parameter change transforms the dye's properties: it reduces side-absorption in the visible range while enhancing the formation of colored products upon IR exposure, thereby improving print-out image contrast without requiring additional contrasting dyes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite dye molecule combining the indolenine core structure with specific electron-withdrawing groups (cyano, nitro, or carbonyl substituents). This composite structure integrates multiple functions within a single molecule: IR absorption capability, reduced visible side-absorption, and enhanced colored product formation upon exposure, eliminating the need for separate contrasting dye components.

Inventive Principle:
Principle #40Composite materials

2Measurement precision

If additional contrasting dyes are added to improve print-out image visibility, then the contrast improves, but the device complexity and risk of dye stain increase

Engineering Contradiction:
Improvevisibility of exposed areasVSAvoidnumber of dye components
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The modified IR dye performs multiple functions simultaneously: it absorbs IR radiation for image formation, provides sufficient visible contrast through colored product formation upon exposure, and maintains stability without requiring additional contrasting dye components. This multi-functionality simplifies the overall system by eliminating the need for separate contrasting dye additions.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent merges the functions of IR absorption and contrast formation into a single modified dye molecule. The electron-withdrawing substituents on the indolenine ring enable the same molecule that absorbs IR radiation to also produce high-contrast colored products upon exposure, consolidating multiple dye functions into one component and reducing system complexity.

Inventive Principle:
Principle #5Merging (Combining)

3Measurement precision

If the IR dye forms colored products upon exposure, then the print-out image contrast improves, but the optical density in the visible spectrum must be increased

Engineering Contradiction:
Improvecontrast of print-out imageVSAvoidoptical density in visible spectrum
Core Design Contradiction:
Measurement precisionVSIllumination intensity

Solution Approach 1:

The patent changes the chemical parameters of the IR dye by introducing electron-withdrawing substituents that specifically enhance the optical density of the colored products formed upon IR exposure. These substituents (cyano, nitro, or carbonyl groups at positions 5 and 6) increase the visible spectrum absorption of the exposed areas, thereby improving print-out image contrast through enhanced colored product formation rather than by increasing the overall optical density of the unexposed dye.

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 new IR dye significantly improves the contrast of print-out images by increasing optical density in the visible spectrum, allowing for better differentiation between exposed and non-exposed areas without the need for additional contrasting dyes, leading to improved print quality and reduced risk of dye stain.

Implementation Method 1

The material is exposed to heat or to infrared radiation and the generated heat triggers a (physico-)chemical process

Methodology Applied
Scientific EffectInfrared absorption: Absorption (EM radiation)

Implementation Method 2

the generated heat triggers a (physico-)chemical process, such as ablation, polymerization, insolubilization by cross-linking

Methodology Applied
Scientific EffectPhotothermal conversion: Heating

Implementation Method 3

The IR dye is capable of forming a colour upon exposure to IR-radiation or heat. The coloration may be the result of a chemical transformation upon exposure to IR-light or heat of at least one Rd group

Methodology Applied
Scientific EffectPhotoinduced coloration: Photochromism

Data Source

PatentEP1910082B1Infrared absorbing dye
Publication Date: 2014.01.22 AGFA NV
  • EP1910082B1 patent drawingFigure 1~2
  • EP1910082B1 patent drawing
  • EP1910082B1 patent drawing

AI summary

The present invention relates to an infrared absorbing dye as defined in claim 1. The present invention relates also to a heat- sensitive imaging element comprising said IR dye and more particularly to a heat-sensitive lithographic printing plate precursor comprising said IR dye. The present invention relates also to a method for making a lithographic printing plate whereby a print-out image of high contrast is formed upon exposure to IR- radiation or heating.