Acrylated Epoxy-Amine Oligomers for Low Migration UV Curing

Solution Overview

Problem

There is a need for new classes of oligomers suitable for use in radiation-curable compositions such as UV or EB-curable inks, coatings, and laminating adhesives, as existing technologies have limitations in terms of curing properties and component migration.

Innovation Solution

The development of amine-terminated copolymers derived from diglycidyl ether and amines, specifically difunctional secondary amines or monofunctional primary amines, which are subsequently reacted with multifunctional acrylate monomers to create reactive components for UV or EB-curable compositions, offering high functionality and low component migration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing epoxy-amine oligomers are used in radiation-curable compositions, then curing properties are achieved, but component migration occurs and limits performance

Engineering Contradiction:
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the chemical structure of epoxy-amine oligomers by controlling the amine-to-epoxy ratio (0.5-2.0:1) and using specific amine types (cyclic, aliphatic, aromatic) to create oligomers with reduced component migration while maintaining curing properties. The molecular weight and functional group composition are adjusted to optimize performance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite oligomer structures by reacting epoxy compounds with amines to form amine-terminated oligomers, which are then incorporated into radiation-curable compositions alongside other reactive components. This composite approach combines the advantages of epoxy-amine chemistry with the benefits of radiation curing to achieve low migration and excellent curing properties.

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If new classes of oligomers are developed for radiation-curable compositions, then component migration is reduced, but manufacturing complexity increases

Engineering Contradiction:
Core Design Contradiction:
Object-generated harmful factorsVSDevice complexity

Solution Approach 1:

The patent divides the oligomer synthesis into distinct stages: first forming amine-terminated oligomers by reacting epoxy compounds with excess amine, then using these as components in radiation-curable compositions. This segmentation allows for controlled production and simplifies the overall manufacturing process while achieving low migration.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention simplifies manufacturing by establishing specific parameter ranges for the amine-to-epoxy ratio (0.5-2.0:1) and molecular weight characteristics, which standardize the production process and reduce complexity while maintaining the low migration property.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If oligomers with specific functionality are synthesized, then curing properties are improved, but production cost increases

Engineering Contradiction:
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent optimizes the amine-to-epoxy ratio to fall within 0.5-2.0:1, which balances functionality and cost. This parameter optimization ensures sufficient curing properties while avoiding excessive production costs associated with extreme ratios or specialized materials.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The amine-terminated oligomers synthesized according to the patent can be used in multiple radiation-curable composition types (inks, coatings, adhesives, laminating compositions), providing universal applicability that amortizes production costs across diverse applications while maintaining excellent curing properties.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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

These reactive components provide compositions with excellent curing properties, low migration of components, and can be tailored for specific applications, such as lithographic uses, with desirable properties like viscosity and hydrophobicity, and are cost-effective to produce.

Implementation Method 1

The present invention relates to the radiation-curable Michael addition product of a multifunctional acrylate monomer with a secondary amine-terminated oligomer

Methodology Applied
Scientific EffectMichael addition: Chemical Bonding

Implementation Method 2

Free-radical curable components include functional groups that cross-link under irradiation via a free radical mechanism to form a hardened film

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Implementation Method 3

The reactive components include functional groups which react with one another in the radiation induced curing reaction to form chemical cross-links thus providing a hardened cured film

Methodology Applied
Scientific EffectCross-linking: Chemical Bonding

Data Source

PatentEP2356160B1Acrylated epoxy-amine oligomers
Publication Date: 2019.05.22
  • EP2356160B1 patent drawing
  • EP2356160B1 patent drawing
  • EP2356160B1 patent drawing

AI summary

A reactive component suitable for use in a radiation-curable composition, which comprises an acrylated epoxy-amine oligomer represented by the formula (I): C-B-[A-B]n-A-B-C wherein: n is from 2 to 500; each A is individually a unit derived from a diglycidyl ether; each B is individually a unit derived from a difunctional secondary amine or a monofunctional primary amine; and each C is individually a unit derived from a multifunctional acrylate monomer, radiation-curable compositions, such as inks, coatings and adhesives, comprising said reactive component and methods of making said reactive component.