Polymer-Bound Bisacylphosphine Oxides via Phosphorus Linkage

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Solution Overview

Problem

Current polymer-bound bisacylphosphine oxide photoinitiators are limited to monoacylphosphine oxide structures with the link to the carrier primarily through the benzoyl moiety, lacking high radical density and reactivity, particularly when the photoactive moiety is linked via the phosphorous atom to the polymer or carrier material.

Innovation Solution

Development of oligomers or polymers with bisacylphosphine oxide moieties linked via the phosphorous atom, optionally through a spacer group, to the polymer or oligomer backbone, allowing for higher radical density and reactivity, and the use of corresponding functionalized intermediates in their preparation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If polymer-bound photoinitiators are used with link via benzoyl moiety, then ease of manufacture is improved, but radical density and reactivity are insufficient

Engineering Contradiction:
Improveease of manufactureVSAvoidreactivity
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent inverts the conventional linkage approach by connecting the photoinitiator moiety through the phosphorous atom instead of the traditional benzoyl moiety. This inversion enables direct attachment of the photoactive group to the polymer backbone, creating high radical density at the carrier material interface and significantly improving reactivity while maintaining ease of manufacture through straightforward chemical bonding

Inventive Principle:
Principle #13The other way round (Inversion)

2Ease of manufacture

If monoacylphosphine oxide structures are used, then ease of manufacture is improved, but radical density is insufficient

Engineering Contradiction:
Improveease of manufactureVSAvoidradical density
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent combines multiple acylphosphine oxide moieties (bisacylphosphine oxide structures) into a single polymer-bound photoinitiator molecule. This merging approach doubles the number of photoactive groups per molecular unit, thereby doubling the radical density generated upon photolysis, while the polymer backbone provides a convenient framework for incorporating these multifunctional units

Inventive Principle:
Principle #5Merging (Combining)

3Reliability

If photoinitiators linked via phosphorous atom are used, then reactivity is improved, but device complexity increases

Engineering Contradiction:
ImprovereactivityVSAvoidstructural complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by concentrating the photoactive functionality directly at the phosphorous atom linkage point on the polymer backbone. This localized arrangement ensures that the region most critical for reactivity (the photoinitiator-polymer interface) has maximum photoactive group density, while the rest of the polymer structure remains relatively simple and flexible

Inventive Principle:
Principle #3Local quality

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

This approach enhances the reactivity and performance of photopolymerizable compositions by achieving high radical density on the carrier material, leading to improved curing properties and application in various fields such as coatings and printing inks.

Implementation Method 1

Bisacylphosphine oxide photoinitiators absorb light in the UV-A/vis region and undergo concomitant photobleaching, which provides unique curing properties

Methodology Applied
Scientific EffectPhotobleaching: Photodissociation

Implementation Method 2

the product is obtained by homopolymerization or copolymerization of a functionalized bisacylphosphine oxide compound

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP2451847B1Polymer-bound bisacylphosphine oxides
Publication Date: 2021.11.24 IGM GROUP
  • EP2451847B1 patent drawing
  • EP2451847B1 patent drawing
  • EP2451847B1 patent drawing

AI summary

The invention pertains to an oligomer or polymer substituted by one or more bisacylphosphine oxide moieties, characterized in that said bisacylphosphine oxide moiety is linked via the phosphorous atom, optionally via a spacer group, to the oligomer or polymer backbone; as well as to specifically functionalized bisacylphosphine oxides, suitable to prepare said polymers or oligomers.