Radiation Curable (Meth)acrylated Compounds with Cyclic Ether Polyols

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

The need for renewable alternatives to petroleum-based radiation curable resins, particularly to replace Bisphenol A, which is reprotoxic, and to address the depletion of petroleum supplies and increasing market prices of petrochemical-derived products, while ensuring safety and sustainability.

Innovation Solution

Development of (meth)acrylated compounds prepared from a polyol constituent, a polyacid constituent, and (meth)acrylating compounds, where the polyol constituent comprises at least 30% cyclic ether polyols, optionally containing moieties like (poly)caprolactone, (poly)lactide, epoxide, and alkylene oxide groups, facilitating fast curing, low viscosity, and non-toxicity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If petrochemical derived radiation curable resins are used, then good performance and availability are achieved, but sustainability and environmental friendliness deteriorate due to petroleum depletion and reprotoxicity of Bisphenol A

Engineering Contradiction:

Improveperformance reliabilityVSAvoidenvironmental harm and reprotoxicity

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by using bioderived cyclic ether polyols (at least 30% by weight) instead of petrochemical Bisphenol A, while maintaining the radiation curable properties through inclusion of (meth)acrylating compounds. This parameter change achieves both sustainability and performance reliability.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite radiation curable resin system combining bioderived cyclic ether polyols with (meth)acrylating compounds and optionally other functional moieties. This composite approach maintains the desirable performance characteristics while eliminating harmful petrochemical components.

Inventive Principle:

Principle #40Composite materials

2Object-affected harmful factors

If bioderived cyclic ether polyols are used, then sustainability and renewability are improved, but curing speed and mechanical properties may deteriorate

Engineering Contradiction:

ImprovesustainabilityVSAvoidcuring speed

Core Design Contradiction:

Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent applies local quality by incorporating specific functional moieties (epoxide groups, alkylene oxide groups, lactone-containing moieties) at strategic positions within the polymer structure to enhance curing speed and mechanical properties in those specific regions, while maintaining the overall sustainability benefit of using bioderived cyclic ether polyols.

Inventive Principle:

Principle #3Local quality

Solution Approach 2:

By creating a composite system that combines bioderived cyclic ether polyols with specifically selected (meth)acrylating compounds and functional moieties, the invention achieves both sustainability and enhanced curing performance through synergistic interactions between different components.

Inventive Principle:

Principle #40Composite materials

3Object-affected harmful factors

If oligomeric or polymeric compounds are used to replace Bisphenol A, then non-toxicity and migration resistance are improved, but formulation complexity and manufacturing difficulty increase

Engineering Contradiction:

ImprovetoxicityVSAvoidformulation ease

Core Design Contradiction:

Object-affected harmful factorsVSEase of manufacture

Solution Approach 1:

The patent achieves universality by designing a polyol constituent that can be prepared from multiple bioderived cyclic ether polyols (at least 30% by weight) and that serves multiple functions: providing non-toxicity, reducing migration, enabling fast curing, and maintaining good mechanical properties. This multi-functional approach simplifies formulation despite the complexity of the individual components.

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

The resulting compounds offer fast curing, low viscosity, non-toxicity, and high renewable content, enabling the production of radiation curable resins with improved mechanical properties, adhesion, and resistance to oxygen inhibition, suitable for applications such as food packaging and coatings without the need for Bisphenol A.

Implementation Method 1

Radiation curable (meth)acrylated compounds may be produced commercially from petrochemical sources

Methodology Applied

Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS9540310B2Radiation curable (meth)acrylated compounds

Publication Date: 2017.01.10 ALLNEX BELGIUM SA

AI summary

The present invention relates to a (meth)acrylated compound (A) prepared from: (i) a polyol constituent, (ii) a polyacid constituent and (iii) one or more (meth)acrylating compounds, wherein the polyol constituent comprises at least 30% by weight of one or more cyclic ether polyols, relative to the total weight of the polyol constituent, and wherein the compound (A) optionally further contains one or more moieties selected from the group consisting of (poly)caprolactone-containing moieties (ai), (poly)lactide- and/or (poly)glycolide-containing moieties (aii), moieties providing epoxide groups (aiii) and moieties providing alkylene oxide groups containing from 2 to 4 carbon atoms (aiv). The compounds of the invention are in particular suited for the making of radiation curable coating compositions and inks less prone to migration.