Radiation Curable Methacrylated Compounds for Coatings

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Solution Overview

Problem

The market lacks a broad range of bio-derived radiation curable (meth)acrylated compounds suitable for coatings, inks, overprint varnishes, adhesives, and composites, which are essential for sustainable and environmentally friendly applications, as existing derivatives are limited in variety and functionality.

Innovation Solution

A radiation curable composition comprising at least 5% by weight of (meth)acrylated compounds prepared from cyclic ether polyols, aliphatic linking compounds, and (meth)acrylating compounds, which offer fast curing, non-toxicity, low viscosity, and high renewable content, along with improved mechanical properties and resistance to oxygen inhibition.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If direct acrylation of polyols is used, then the synthesis is simple, but the product range and functionality are limited

Engineering Contradiction:
Improvesynthesis simplicityVSAvoidproduct range
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The synthesis process is divided into multiple stages: first forming cyclic ether polyols from renewable feedstock, then reacting with aliphatic linking compounds, and finally acrylating to introduce reactive groups. This segmentation allows independent optimization of each step and enables access to diverse intermediate structures that can be tailored for specific applications.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Aliphatic linking compounds serve as intermediary agents between the cyclic ether polyol backbone and the acrylating compound. These intermediaries provide structural flexibility and enable the introduction of various functional groups, thereby expanding the range of final products while maintaining a systematic synthesis approach.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If aromatic (meth)acrylated derivatives are used, then chiral properties are achieved, but yellowing and toxicity increase

Engineering Contradiction:
Improvechiral propertiesVSAvoidyellowing and toxicity
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

Instead of using aromatic rings to achieve structural rigidity and chiral properties, the invention inverts the approach by utilizing cyclic ether structures with aliphatic linkages. This inversion maintains the desired mechanical properties and chiral characteristics while eliminating the yellowing and toxicity associated with aromatic compounds.

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The chemical composition parameters are changed from aromatic to aliphatic structures. This parameter change fundamentally alters the photochemical stability and toxicity profile while preserving the chiral properties needed for specific applications, thereby reducing harmful effects without sacrificing functional performance.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If high renewable content is achieved, then environmental sustainability improves, but the variety of available compounds decreases

Engineering Contradiction:
Improveenvironmental sustainabilityVSAvoidcompound variety
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The cyclic ether polyol platform serves as a universal backbone that can be combined with various aliphatic linking compounds and acrylating agents. This multi-functionality allows a single renewable feedstock to generate a diverse range of compounds tailored for different applications, thereby maintaining environmental sustainability while achieving compound variety.

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

Solution Approach 2:

The invention creates composite molecular structures by combining renewable cyclic ether polyols with synthetically diverse aliphatic linkages and acrylate groups. This composite approach leverages the sustainability of biological feedstock while incorporating the versatility of synthetic chemistry to produce a broad range of functional materials.

Inventive Principle:
Principle #40Composite materials

4Productivity

If fast curing is achieved, then productivity increases, but oxygen inhibition resistance may be compromised

Engineering Contradiction:
Improvecure speedVSAvoidoxygen inhibition resistance
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention replaces traditional free-radical polymerization mechanisms with a system based on cationic photopolymerization initiated by specific photoinitiators. This mechanism substitution enables fast curing rates while inherently providing better resistance to oxygen inhibition, as cationic polymerization is less susceptible to oxygen interference compared to radical mechanisms.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 enables the production of coatings with enhanced scratch and abrasion resistance, impact resistance, and low yellowing, suitable for food packaging and composite materials, while maintaining high UV reactivity and excellent adhesion, thus addressing the need for sustainable and effective bio-derived alternatives.

Implementation Method 1

radiation curable composition

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP2831032B1Radiation curable (METH)acrylated compounds
Publication Date: 2018.06.13 ALLNEX BELGIUM SA
  • EP2831032B1 patent drawing
  • EP2831032B1 patent drawing
  • EP2831032B1 patent drawing

AI summary

The present invention relates to (meth)acrylated compounds (A) prepared from (a) at least one cyclic ether polyol, (b) at least one linking compound (b1) and/or (b2), wherein the linking compound (b1) is selected from cyclic compounds (b11) containing at least one (I) group in the cycle where X = O or NH, from hydroxy acids (b12) and/or from alkylene oxides (b13) containing from 2 to 4 carbon atoms and the linking compound (b2) is selected from epihalohydrins or polyisocyanates, (c) a (meth)acrylating compound; and to their use in radiation curable compositions for the coatings, inks, overprint varnishes, adhesives and composites.