Photobase Generator Amide Skeleton for Stable Photopolymerization
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Solution Overview
Problem
Non-ionic photobase generators used in photopolymerization processes generate weak bases and are prone to decarboxylation reactions when exposed to light, leading to instability and reduced reactivity in resin compositions.
Innovation Solution
A photobase generator compound with a specific structure, featuring a first skeleton and a second skeleton forming an amide group, generates a base with a hydrogen atom bonding to the nitrogen atom upon light irradiation, having a pKa of 12 or more for its conjugate acid, preventing decarboxylation and enhancing reactivity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Stability of the object's composition
If non-ionic photobase generators are used to improve stability and solubility, then storage stability is improved, but reactivity when irradiated with light deteriorates because weak bases are generated
Solution Approach 1:
The invention changes the chemical structure parameters of the photobase generator by introducing specific skeletal frameworks (first skeleton with formula (a) and second skeleton with formula (1)-12 to (1)-14) to create a novel compound structure that generates strong bases with pKa≥12, thereby improving reactivity while maintaining storage stability
2Stability of the object's composition
If non-ionic photobase generators are used to avoid ionic structure problems, then solubility is improved, but decarboxylation reactions occur during light irradiation
Solution Approach 1:
The invention modifies the molecular structure by combining specific first and second skeletons to create photobase generators that do not undergo decarboxylation reactions, eliminating the harmful effect while preserving the solubility advantages of non-ionic structures
3Reliability
If ionic photobase generators are used to achieve high reactivity through strong base generation, then reactivity is improved, but storage stability and solubility deteriorate
Solution Approach 1:
The invention creates a composite molecular structure combining two distinct skeletal frameworks (first skeleton and second skeleton) to synthesize novel photobase generator compounds that integrate the advantages of both ionic (strong base generation) and non-ionic (storage stability and solubility) structures
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 proposed photobase generator improves the reactivity of photopolymerizable compositions by preventing decarboxylation reactions, ensuring high stability and solubility, and producing a reaction product with enhanced properties.
Implementation Method 1
a photobase generator, comprising a compound including a first skeleton represented by the following formula (a), and a second skeleton including a nitrogen atom bonding to a bonding position of the first skeleton to form an amide group, wherein the compound generates a base, in which a hydrogen atom is bonding with the nitrogen atom of the second skeleton, by light irradiation
Data Source
AI summary
A photobase generator includes a compound including a first skeleton represented by the following formula (a), and a second skeleton including a nitrogen atom bonding to a bonding position of the first skeleton to form an amide group, wherein the compound generates a base, in which a hydrogen atom is bonding with the nitrogen atom of the second skeleton, by light irradiation, and the pKa of a conjugate acid of the base in water is 12 or more. In formula (a), G is a divalent aromatic group, and * represents the bonding position with the nitrogen atom.