Bio-derived Oligomeric UV Stabilizers for Polymers

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Solution Overview

Problem

Conventional UV stabilizers for polymers, such as benzotriazoles and benzophenones, leach from polymer matrices, causing health and environmental concerns, and high molecular weight alternatives face dispersion and degradation issues, limiting their effectiveness.

Innovation Solution

Development of bio-derived oligomeric UV stabilizers with controlled molecular weights (1000-3000 Da) formed through direct carbon-carbon bond formation, using laccase-catalyzed oxidative polymerization of natural monomers like curcumin and vanillin derivatives, which are less prone to degradation and leaching, and can be easily dispersed in polymer matrices.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If small organic compounds (SOCs) such as benzophenones and benzotriazoles are used as UV stabilizers, then UV protection performance is achieved, but leaching from polymer matrix occurs causing health and environmental issues

Engineering Contradiction:
ImproveUV protection performanceVSAvoidleaching and toxicity
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent divides the UV stabilizer function into oligomeric structures composed of multiple monomer units linked by carbon-carbon bonds. This segmentation increases molecular weight and complexity, reducing leaching while maintaining UV absorption capability through the preserved chromophore structures within the oligomer chain.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates composite oligomeric structures by combining natural monomer units (such as curcumin and vanillin derivatives) through carbon-carbon bond formation. These composite structures integrate the UV-absorbing properties of natural compounds with enhanced stability and reduced leaching characteristics.

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If high molecular weight UV stabilizers (>15 000 Da) are used to reduce leaching rates, then leaching is reduced, but dispersion issues and UV degradation susceptibility increase

Engineering Contradiction:
Improveleaching rateVSAvoiddispersion and UV stability
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The patent optimizes the molecular weight parameter of UV stabilizers by creating oligomers in the 1000-3000 Da range. This parameter change is sufficient to reduce leaching rates compared to small organic compounds, yet maintains good dispersion properties and UV stability unlike high molecular weight polymers. The oligomeric structure provides the right balance of molecular size for all required properties.

Inventive Principle:
Principle #35Parameter changes

3Weight of moving object

If amide or ester groups are used for molecular weight increase, then molecular weight increases, but bond stability decreases making UV stabilizer more prone to degradation

Engineering Contradiction:
Improvemolecular weightVSAvoidbond stability
Core Design Contradiction:
Weight of moving objectVSStability of the object's composition

Solution Approach 1:

The patent uses direct carbon-carbon bond formation to link monomer units, copying the stability of natural aromatic structures. This approach avoids introducing labile functional groups like amides or esters, instead utilizing the inherent stability of carbon-carbon bonds found in natural aromatic compounds to achieve both molecular weight increase and enhanced stability.

Inventive Principle:
Principle #26Copying

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 oligomeric UV stabilizers demonstrate comparable UV blocking performance to commercial stabilizers, with minimal leaching and improved stability, suitable for applications in food packaging, sunscreens, textiles, and coatings, while being environmentally friendly and non-toxic.

Implementation Method 1

laccase-catalyzed oxidative polymerization of natural monomers like curcumin and vanillin derivatives

Methodology Applied
Scientific EffectOxidative polymerization: Oxidation

Implementation Method 2

laccase-catalyzed oxidative polymerization

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

UV absorbers/stabilizers are blended with polymers or plastics during formulation in order to protect them from sunlight

Methodology Applied
Scientific EffectUV absorption: Absorption (EM radiation)

Data Source

PatentUS12180150B2Oligomeric materials for UV blocking applications and methods thereof
Publication Date: 2024.12.31 AGENCY FOR SCI TECH & RES
  • US12180150B2 patent drawing
  • US12180150B2 patent drawing
  • US12180150B2 patent drawing

AI summary

The present invention describes an oligomer for use as a UV stabiliser. In particular, the oligomer is suitable for use as a UV stabiliser in a polymer matrix. The present invention also describes a method of forming said oligomer. The method of forming said oligomer comprises a polymerising step, wherein the polymerising step comprises forming a C—C bond on the hydroxyphenyl ring of a monomer. In preferred embodiments, the oligomer is formed from polymerizing bio-derived monomer such as curcumin, its hydrogenated analogue, and an aldol condensation product of cyclic ketone and vanillin.