Polymerizable Phosphine Oxide Photoinitiators for Low Migration

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Solution Overview

Problem

Current photoinitiators like TPO and TPO-L are classified as SVHC, limiting their use due to toxicity concerns and potential migration of photoproducts like mesitaldehyde, which poses health hazards and contaminates adjacent materials.

Innovation Solution

Development of a polymerizable phosphine oxide-based photoinitiator with (meth)acrylate and/or (meth)acrylamide groups, which reduces migration and bioavailability, mimicking the curing properties of classic initiators while minimizing toxicity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional photoinitiators like TPO and TPO-L are used, then high curing activity is achieved, but toxicity concerns and migration of photoproducts occur

Engineering Contradiction:
Improvecuring activityVSAvoidtoxicity and migration
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent combines the photoinitiator function with polymerizable groups ((meth)acrylate and/or (meth)acrylamide) into a single molecular structure. This merging allows the compound to serve dual purposes: initiating polymerization and becoming part of the polymer network, thereby preventing migration while maintaining curing activity.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention creates a composite molecular structure that integrates the phosphine oxide photoinitiator core with polymerizable functional groups. This composite approach enables the photoinitiator to be incorporated into the polymer matrix, reducing its ability to migrate while preserving its photoinitiation capabilities.

Inventive Principle:
Principle #40Composite materials

2Reliability

If polymerizable groups are added to the photoinitiator structure, then migration is reduced, but molecular weight increases

Engineering Contradiction:
Improvemigration resistanceVSAvoidmolecular weight
Core Design Contradiction:
ReliabilityVSWeight of moving object

Solution Approach 1:

The patent modifies the molecular parameters of the photoinitiator by adding polymerizable groups, which changes its physical and chemical properties. This parameter change enables the photoinitiator to participate in polymerization and become part of the network structure, thereby improving migration resistance despite the increase in molecular weight.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If photoinitiator residue is reduced to meet health standards, then biocompatibility improves, but curing effectiveness may be compromised

Engineering Contradiction:
ImprovebiocompatibilityVSAvoidcuring effectiveness
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent converts the potential harm of photoinitiator migration and residue into a benefit by designing a structure where the photoinitiator becomes part of the polymer network. This transformation ensures that the photoinitiator remains in the cured product without migrating, meeting health standards while maintaining curing effectiveness through its integrated structure.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 polymerizable photoinitiator achieves high curing activity with reduced toxicity and migration, making it suitable for applications where health and safety standards must be met, such as in biomedical devices and food contact materials.

Implementation Method 1

Radiation curable compositions containing ethylenically unsaturated compounds can be polymerized by exposure to radiation, such as ultraviolet (UV) light. For rapid and effective curing, a photoinitiator is often used. The photoinitiator forms radical species upon irradiation with photons and initiates free-radical polymerization of unsaturated groups

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Implementation Method 2

Acylphosphine oxides are classified as Norrish Type I initiators and include the following compounds... phosphine oxide derivatives such as acylphosphine oxides are the preferred class of photoinitiators because of their strong absorbance in the wavelength range of interest

Methodology Applied
Scientific EffectAbsorption (EM radiation): Absorption (EM radiation)

Data Source

PatentEP4570811A1Polymerizable phosphine oxide-based photoinitiators
Publication Date: 2025.06.18 ARKEMA FRANCE SA
  • EP4570811A1 patent drawingFigure 1~2
  • EP4570811A1 patent drawing
  • EP4570811A1 patent drawing

AI summary

The present invention relates to a polymerizable phosphine oxide-based photoinitiator, to a process for preparing said photoinitiator and to a precursor that may be used to prepare said photoinitiator. The present invention further relates to a photoinitiator composition, to a curable composition, to a process for the preparation of a cured product, to a process of inkjet printing, to a process of 3D printing and to a process for coating a nail. The invention also relates to precursors of the photoinitiator or the photoinitiator composition. The invention also relates to the use of the photoinitiator or the photoinitiator composition.