Aromatic Amine Acrylates for UV Curing
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Solution Overview
Problem
Current amine synergists used in radiation curing face issues such as water solubility, strong odors, migratable species, and photo-yellowing, which affect the quality and stability of UV-cured coatings, particularly in applications like food packaging and electronics.
Innovation Solution
Development of aromatic amine acrylates that are synthesized through a simple process, allowing for the creation of multifunctional compounds that act as efficient synergists with low odor and minimal migratable species, effectively reducing oxygen inhibition and enhancing polymerization efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional amine synergists (aliphatic or aromatic) are used in radiation curing, then polymerization efficiency is improved, but water solubility, strong odors, migratable species, and photo-yellowing occur
Solution Approach 1:
The patent creates composite amine synergist molecules combining aromatic and aliphatic components. The aromatic portion provides odor resistance and photo-stability, while the aliphatic portion maintains high polymerization efficiency. This composite structure resolves the contradiction by integrating complementary properties from both amine types into a single molecule that delivers both high productivity and reduced harmful factors.
Solution Approach 2:
The patent introduces functional differentiation within the amine synergist molecule by placing specific functional groups in strategic positions. The aromatic ring structure localizes odor resistance and UV stability properties, while the aliphatic amine portion localizes reactivity toward (meth)acrylate double bonds. This local quality assignment allows the molecule to simultaneously achieve high polymerization efficiency and resistance to yellowing and migration.
2Ease of operation
If aliphatic amine synergists are used, then high reactivity and optical transparency are achieved, but strong odors and photo-yellowing occur
Solution Approach 1:
The patent merges the beneficial properties of aromatic and aliphatic amines into a single hybrid molecule. The aromatic component contributes optical transparency and odor resistance, while the aliphatic component provides high reactivity with (meth)acrylate double bonds. This merging resolves the contradiction by creating a unified synergist that exhibits both high ease of operation and reduced harmful factors.
3Object-generated harmful factors
If aromatic amine synergists are used, then low water solubility and odor resistance are achieved, but reduced reactivity compared to aliphatic amines
Solution Approach 1:
The patent designs composite amine synergists where the aromatic portion provides water solubility resistance and odor resistance, while the aliphatic amine portion maintains high reactivity toward (meth)acrylate double bonds. This composite approach resolves the contradiction by distributing different functional properties to different molecular regions, achieving both low harmful factors and high ease of operation.
4Productivity
If tertiary amines are used to scavenge oxygen, then polymerization efficiency is improved, but extractable amine content increases in cured coatings
Solution Approach 1:
The patent creates composite amine synergists with increased molecular weight through the combination of aromatic and aliphatic portions. This increased molecular weight reduces the extractability of the amine from the cured coating while maintaining the tertiary amine functionality needed for oxygen scavenging. The composite structure thus resolves the contradiction by reducing migration and extraction while preserving polymerization efficiency.
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 aromatic amine acrylates provide improved cure rates, reduced extractable amine content in coatings, and enhanced physical properties like hardness and weather resistance, making them suitable for diverse applications including food packaging and electronics.
Implementation Method 1
radicals generated from the amine rapidly scavenge oxygen present in the formulation
Implementation Method 2
directly related to their mechanism of photooxidation
Implementation Method 3
it is necessary for formulations based on (meth)acrylates to contain a material that will absorb light and thereby generate a species which will initiate polymerisation
Implementation Method 4
use ultra-violet, visible and near infra-red radiation to bring about the polymerisation of unsaturated species
Implementation Method 5
the alpha-aminoalkyl radicals produced from tertiary amines react rapidly with oxygen to produce peroxyl radicals. These peroxyl radicals can then attack tertiary amines that have yet to form radicals, thus generating further alpha-aminoalkyl radicals
Data Source
AI summary
Compounds of formula (I): wherein Ar represents an, optionally substituted, aryl or heteroaryl group, R represents an, optionally substituted, aryl or heteroaryl group, an optionally substituted straight or branched chain C1.10-alkyl, R1 is H or methyl, X is an extender group, n is 0 or an integer between 1 and 12 inclusive, A is a polyol residue wherein the unsubstituted polyol from which the residue is derived has at least y OH groups, and y is an integer>1, can easily be prepared, and are useful as synergists in radiation curing.