Biobased Degradable Copolymers via Radical Ring-Opening

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Solution Overview

Problem

Current methods for producing degradable polymers face challenges such as high energy consumption, use of toxic ingredients, limited applicability, and inability to degrade under mild or moderate conditions, leading to environmental pollution and reduced performance properties.

Innovation Solution

A method for producing copolymers through radical polymerization of ketene acetals and crotonic esters using alternating radical ring-opening polymerization with partial ring-opening, resulting in biobased and degradable copolymers suitable for various applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used to produce degradable polymers, then polymer production is achieved, but high energy consumption occurs

Engineering Contradiction:
Improvepolymer productionVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent changes the chemical parameters of the polymerization process by using ketene acetal monomers with specific ring structures that enable ring-opening polymerization. This chemical parameter change allows the reaction to proceed under milder conditions with lower energy input while maintaining high productivity in copolymer production.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional polymerization methods are used, then polymer production is achieved, but toxic ingredients are required

Engineering Contradiction:
Improvepolymer productionVSAvoidtoxic ingredients
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by selecting specific monomers (ketene acetals and crotonic acid esters) that can polymerize without requiring toxic catalysts or initiators. The ring-opening mechanism of ketene acetals provides a toxic-free pathway for copolymer production while maintaining high productivity.

Inventive Principle:
Principle #35Parameter changes

3Object-generated harmful factors

If conventional degradable polymers are used, then degradation is achieved, but degradation requires harsh conditions

Engineering Contradiction:
ImprovedegradabilityVSAvoiddegradation conditions
Core Design Contradiction:
Object-generated harmful factorsVSTemperature

Solution Approach 1:

The patent changes the chemical structure parameters of the polymer backbone by incorporating ketene acetal units that form ester linkages through ring-opening. These ester bonds have controlled lability that allows degradation under mild physiological or environmental conditions, eliminating the need for harsh temperature or chemical conditions while maintaining degradability.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If conventional methods are used to produce degradable polymers, then polymer production is achieved, but environmental pollution occurs

Engineering Contradiction:
Improvepolymer productionVSAvoidenvironmental pollution
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the environmental parameters by using biobased monomers and a polymerization mechanism that produces no harmful byproducts. The ring-opening copolymerization of ketene acetals with crotonic acid esters creates degradable copolymers that can be produced sustainably, eliminating environmental pollution while maintaining high productivity.

Inventive Principle:
Principle #35Parameter changes

5Object-generated harmful factors

If conventional degradable polymers are used, then degradation is achieved, but performance properties are reduced

Engineering Contradiction:
ImprovedegradabilityVSAvoidperformance properties
Core Design Contradiction:
Object-generated harmful factorsVSStrength

Solution Approach 1:

The patent creates composite copolymer structures by combining ketene acetal units (which provide degradability through ring-opening) with crotonic acid ester units (which provide mechanical strength and stability). This composite approach at the molecular level allows the material to simultaneously achieve degradability and maintain excellent performance properties.

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 method produces copolymers with high biobased content, excellent performance properties, and ease of degradation under defined conditions, overcoming environmental and economic inefficiencies of prior art methods.

Implementation Method 1

producing, via radical polymerization, a copolymer obtainable by copolymerizing monomers (moieties) (i), (ii) and optionally (iii)

Methodology Applied
Scientific EffectRadical polymerization: Photopolymerisation

Implementation Method 2

producing, via radical polymerization, a copolymer obtainable by copolymerizing monomers (moieties) (i), (ii) and optionally (iii) wherein radical polymerization is performed with partial ring-opening of (i) the at least one first ethylenically unsaturated monomer selected from cyclic ketene acetals

Methodology Applied
Scientific EffectRing-opening polymerization: Chemical Bonding

Data Source

PatentEP4511406B1Method for producing biobased degradable copolymers by radical polymerization of ketene acetals and crotonic acid or its esters and copolymers thus produced as well as uses thereof
Publication Date: 2025.10.22 THE UNIV OF THE BASQUE COUNTRY
  • EP4511406B1 patent drawingFigure 1~2
  • EP4511406B1 patent drawingFigure 3~4
  • EP4511406B1 patent drawingFigure 5~6

AI summary

The present invention refers to a method for producing copolymers based on ketene acetals and crotonic acid or its esters or salts, which copolymers allow for a wide range of applications and are particularly useful as a degradable ingredient or component of adhesives, coating materials, lubricants, agricultural products, household cleaners, inks, personal care products, cosmetics, pharmaceuticals, packagings, drug delivery systems or the like, as well as to the copolymers thus produced and to their various applications. The resulting copolymers provide good or even superior performance and application properties while at the same time being environmentally compatible and easy to use and to apply and being producible in an economic way.