Biobased Radiation Curable Composition with MVG Diluent

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Solution Overview

Problem

Current radiation curing compositions face challenges in achieving a higher degree of renewable content while maintaining or improving physical properties such as surface smoothness, mechanical strength, and chemical resistance.

Innovation Solution

A radiation curable composition comprising 51-100 wt% of a cationic curable resin, including a cycloaliphatic epoxide, methyl vinyl glycolate (MVG) or its derivatives as a vinyl compound, and a cationic photoinitiator, which also optionally includes monooxetane or polyoxetane compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If biobased vinyl compounds (MVG) are used to replace petrochemical-based monomers, then renewable content is increased, but curing speed and radiation energy requirements may be affected

Engineering Contradiction:
Improvebiobased contentVSAvoidcuring speed
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent combines cationic and free-radical curing mechanisms in a hybrid radiation curable composition. The cationic curable resin (51-100 wt%) provides biobased content through MVG, while the free-radical curable resin (0-49 wt%) with acrylate monomers ensures rapid curing speed. This merging of two different curing mechanisms allows the composition to achieve both high renewable content and fast curing performance.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention uses a composite resin system comprising both cationic curable resin (based on biobased vinyl compounds like MVG) and free-radical curable resin (acrylate-based). This composite material approach allows the benefits of both systems to be combined: the biobased content and chemical resistance from the cationic component, and the fast curing speed from the free-radical component.

Inventive Principle:
Principle #40Composite materials

2Shape

If MVG is used as a reactive diluent in cationic curable resin, then film forming properties are improved, but the amount of cycloaliphatic epoxide required increases

Engineering Contradiction:
Improvefilm forming propertiesVSAvoidcycloaliphatic epoxide content
Core Design Contradiction:
ShapeVSQuantity of substance

Solution Approach 1:

The patent optimizes the ratio and amount of MVG relative to cycloaliphatic epoxide to achieve the desired balance between film forming properties and epoxide content. By carefully controlling the concentration parameters of these components, the composition achieves excellent film forming with reduced dependence on large amounts of cycloaliphatic epoxide.

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If higher biobased content is achieved through MVG incorporation, then environmental sustainability is improved, but mechanical properties such as hardness and chemical resistance may deteriorate

Engineering Contradiction:
Improverenewable contentVSAvoidmechanical properties
Core Design Contradiction:
Quantity of substanceVSStrength

Solution Approach 1:

The hybrid curing system merges cationic and free-radical mechanisms to achieve both high biobased content and excellent mechanical properties. The cationic curable resin based on MVG provides the biobased content and contributes to chemical resistance, while the free-radical curable resin enhances hardness and overall mechanical strength through rapid crosslinking.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The composite resin system creates a synergistic effect where the biobased cationic curable resin and petrochemical free-radical curable resin complement each other's properties. The resulting cured material exhibits both the sustainability benefits of high renewable content and the mechanical performance required for practical applications.

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 composition achieves excellent film forming properties, improved hardness and chemical resistance, and a quicker cure with reduced radiation energy, while increasing the biobased content and reducing the need for cycloaliphatic epoxides.

Implementation Method 1

Photochemical reaction. Radicals or cations, formed from the reaction of the radiation with the photoinitiator, act as catalysts to solidify, dry, harden, polymerize, or cross-link the liquid formulation.

Methodology Applied
Scientific EffectPhotochemical reaction: Photopolymerisation

Implementation Method 2

MVG has the ability to cure by a free-radical mechanism and form a film upon curing in a free-radical curable composition

Methodology Applied
Scientific EffectFree-radical polymerization: Photopolymerisation

Data Source

PatentEP4179024B1A radiation curable composition comprising a biobased reactive diluent
Publication Date: 2025.06.04 PERSTORP AB
  • EP4179024B1 patent drawingFigure 1
  • EP4179024B1 patent drawing

AI summary

The present invention refers to a radiation curable composition, comprising 51-100 wt% of a cationic curable resin, further comprising a cycloaliphatic epoxide, at least one vinyl compound, selected from the group consisting of methyl vinyl glycolate (MVG), vinyl glycolic acid (VGA) and an ester or polyester of MVG or of VGA, and a cationic photoinitiator. The cationic curable resin may also comprise a monooxetane compound, having one oxetane group and/or a polyoxetane compound, having at least two oxetane groups. Optionally the radiation curable composition of the invention comprises 0-49 wt% of a free-radical curable resin, further comprising a (meth)acrylate monomer or oligomer, and a free-radical photoinitiator. The invention further refers to a coating, ink or adhesive comprising the radiation curable composition of the present invention and to a three-dimensional object obtained through 3D printing using the radiation curable composition of the present invention.