Acylphosphine Oxide Photoinitiator with Acid-Stable Silicone Compatibility

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Solution Overview

Problem

Existing photoinitiators for organopolysiloxane curing systems suffer from poor compatibility, leading to separation during storage and resulting in severe haze of the cure product, and are susceptible to acid cleavage of the silyl ether bond, rendering them incompatible with the silicone matrix.

Innovation Solution

A compound represented by Formula I, which is prepared through specific reaction steps and reacted with hydrosilane in the presence of a platinum-containing catalyst, forming a photoinitiator compatible with organopolysiloxane, maintaining stability and solubility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If photoinitiators with silyl ether bonds are used to improve solubility in organopolysiloxane, then compatibility with silicone matrix is improved, but susceptibility to acid cleavage increases

Engineering Contradiction:
ImprovesolubilityVSAvoidacid cleavage susceptibility
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent removes the problematic silyl ether bond (CH2-OSi) from the photoinitiator structure entirely. Instead, it uses a carbon-carbon bond connecting the photoinitiator to the silicone matrix, which is chemically stable and resistant to acid cleavage while maintaining compatibility and solubility in the organopolysiloxane system.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent creates a composite structure where the photoinitiator is integrated into the silicone matrix through a stable carbon-carbon bond, forming a hybrid system that combines the photoinitiating functionality with the stability and compatibility of the silicone polymer chain.

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If conventional photoinitiators are used, then photoinitiation function is provided, but separation from silicone matrix occurs during storage

Engineering Contradiction:
Improvephotoinitiation functionVSAvoidcompatibility
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent merges the photoinitiator molecule with the silicone matrix through a stable carbon-carbon bond, creating a unified structure that prevents phase separation. The photoinitiator is no longer a separate additive but an integrated component of the silicone polymer system, maintaining homogeneity during storage.

Inventive Principle:
Principle #5Merging (Combining)

3Stability of the object's composition

If silyl ether bonded photoinitiators are used, then solubility problem is addressed, but compatibility with silicone matrix is compromised due to acid cleavage

Engineering Contradiction:
ImprovesolubilityVSAvoidacid cleavage
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent converts the harmful effect of acid cleavage on silyl ether bonds into a beneficial design decision by eliminating the silyl ether bond entirely. The carbon-carbon bond used instead is inherently resistant to acid cleavage, transforming the vulnerability into a strength of the new molecular architecture.

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 resulting photoinitiator is compatible with organopolysiloxane, forming a homogeneous, cloud-free composition that maintains stability and clarity, addressing the issues of separation and acid cleavage.

Implementation Method 1

contacting under reactive conditions and in the presence of a platinum-containing catalyst the compound of Formula I with a hydrosilane

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250215160A1Acylphosphine oxide photoinitiator
Publication Date: 2025.07.03 DOW GLOBAL TECHNOLOGIES LLC
  • US20250215160A1 patent drawing
  • US20250215160A1 patent drawing
  • US20250215160A1 patent drawing

AI summary

The present invention is a compound of Formula I: where R1-R3, m, and n, are defined herein. The compound of the present invention is useful as an intermediate for photoinitiator that is soluble in an ethylenically unsaturated organopolysiloxane.