Oxime Ester Photopolymerization Initiator for Long-Wavelength Light

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Solution Overview

Problem

Existing photopolymerization initiators lack satisfactory sensitivity, particularly for long-wavelength light activation such as 405 nm or 365 nm, which affects the efficiency of photopolymerization processes in applications like photo-curing inks and photoresists.

Innovation Solution

A novel oxime ester compound represented by general formula (I) is introduced as a photopolymerization initiator, which efficiently absorbs long-wavelength light, enhancing the sensitivity of photopolymerization processes. The compound is synthesized using specific reactants and processes, and it is incorporated into a photosensitive composition with ethylenically unsaturated polymerizable compounds and optional components like inorganic fillers and colorants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If conventional O-acyl oxime compounds are used as photopolymerization initiators, then the photosensitive composition can undergo photopolymerization, but the sensitivity is insufficient particularly for long-wavelength light activation

Engineering Contradiction:
Improvelight absorption efficiencyVSAvoidphotopolymerization sensitivity
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent modifies the molecular structure of O-acyl oxime compounds by introducing specific substituents (R1-R6 groups including aromatic rings, heterocyclic groups, and electron-donating/withdrawing groups) to change the absorption spectrum and HOMO-LUMO energy gap, enabling efficient absorption of long-wavelength light (365 nm, 405 nm) while maintaining photopolymerization initiation capability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite photopolymerization initiator systems by combining the novel oxime ester compound with other photopolymerization initiators or sensitizers to achieve synergistic effects, improving overall sensitivity and broadening the absorption spectrum for long-wavelength light activation

Inventive Principle:
Principle #40Composite materials

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 oxime ester compound significantly improves the sensitivity of photopolymerization processes, allowing for effective curing with lower energy requirements, particularly at 365 nm and 405 nm wavelengths, leading to higher efficiency and performance in applications like photo-curing inks and photoresists.

Implementation Method 1

efficiently absorbs long-wavelength light, e.g., 405 nm or 365 nm

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Implementation Method 2

A photosensitive composition contains a polymerizable compound having an ethylenically unsaturated bond and a photopolymerization initiator. A photosensitive composition polymerizes to cure on being irradiated with light

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP2223910B1Oxime esters and photopolymerization initiators containing the same
Publication Date: 2012.11.07 ADEKA CORP
  • EP2223910B1 patent drawing
  • EP2223910B1 patent drawing
  • EP2223910B1 patent drawing

AI summary

An oxime ester compound of formula (I) useful as a photopolymerization initiator. A photopolymerization initiator having the oxime ester compound as an active ingredient is activated through efficient absorption of light of long wavelength, e.g., 405 nm or 365 nm, to exhibit high sensitivity. In formula (I), R1 and R2 are each R11, OR11, COR11, SR11, CONR12R13, or CN; R11, R12, and R13 are each hydrogen, a C1-C20 alkyl group, C6-C30 aryl group, a C7-C30 arylalkyl group, or a C2-C20 heterocyclic group; R3 and R4 are each R11, OR11, SR11, COR11, CONR12R13, NR12COR11, OCOR11, COOR11, SCOR11, OCSR11, COSR11, CSOR11, CN, halogen, or a hydroxyl group; a and b is each 0 to 4; X is oxygen, sulfur, selenium, CR31R32, CO, NR33, or PR34; and R31, R32, R33, and R34 each have the same meaning as R1.