Non-cyclic Enamine Compounds for UV Protection

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Solution Overview

Problem

Existing UV-absorbing compounds used in sunscreens and protective coatings lack stability and longevity when exposed to electromagnetic radiation, leading to rapid degradation and loss of protective efficacy.

Innovation Solution

Development of non-cyclic enamine core compounds that absorb electromagnetic radiation across a wide spectrum, offering improved photostability and physical stability, allowing for extended operational lifespan and effective incorporation into various materials like lenses and polymeric products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If organic sunscreen agents are used to absorb UV light, then protection from UV radiation is provided, but the compounds undergo degradation through fragmentation and isomerisation, reducing their operational lifespan

Engineering Contradiction:
Improveprotective efficacyVSAvoidoperational lifespan
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent modifies the molecular structure parameters of conventional enaminoketone compounds by introducing specific substituent groups (aromatic rings, heteroatoms, electron-withdrawing groups) to alter their photostability characteristics. These structural parameter changes enable the compounds to resist degradation pathways while maintaining UV absorption capability, thereby extending operational lifespan without sacrificing protective efficacy

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the enaminoketone core with various stabilizing substituents and auxiliary chromophores. This composite approach integrates multiple functional elements within a single molecule - the core provides UV absorption while the substituents provide photostability - resolving the contradiction between effectiveness and durability

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If cyclic enaminoketone compounds are used for UV absorption, then coverage throughout the UV range is achieved, but stability to electromagnetic radiation exposure is insufficient

Engineering Contradiction:
ImproveUV range coverageVSAvoidphotostability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent applies local quality modification by introducing specific substituent groups at particular positions on the enaminoketone core structure. Different substituents are placed at different locations to optimize both the absorption spectrum coverage and the photostability locally, allowing the molecule to simultaneously achieve broad UV range protection and enhanced radiation stability

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The substituent groups act as intermediary elements between the UV radiation and the core enaminoketone structure. These intermediaries (substituents) absorb or dissipate radiation energy before it can cause damaging effects to the core structure, thereby maintaining both broad spectral coverage and high photostability

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If compounds are incorporated into solid phase polymeric products like lenses, then UV protection is provided, but the compounds must withstand harsh initiating and curing conditions which accelerate degradation

Engineering Contradiction:
Improveprotective functionVSAvoidstability under processing conditions
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent employs preliminary action by designing compounds with inherent photostability features and chemical robustness before incorporation into the polymer matrix. The molecules are pre-engineered with stabilizing substituents and protective structural elements that enable them to withstand the harsh conditions of polymer initiation and curing processes, ensuring long-term stability once incorporated into the final product

Inventive Principle:
Principle #10Preliminary action

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 non-cyclic enamine core compounds demonstrate enhanced stability and effectiveness in absorbing UV and visible light, maintaining protective properties even after exposure to harsh conditions, such as lens casting and prolonged irradiation, providing a longer-lasting solution for UV protection.

Implementation Method 1

compounds capable of absorbing energy to thereby provide a protective effect... compounds for absorbing electromagnetic radiation... absorb the UV light and must then emit this energy

Methodology Applied
Scientific EffectElectromagnetic radiation absorption: Absorption (EM radiation)

Implementation Method 2

Such energy loss can occur by any or all of a variety of pathways such as fluorescence

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP3204347B1Enamine compounds for protecting against UV radiation
Publication Date: 2024.10.23 COMMONWEALTH SCI & IND RES ORG
  • EP3204347B1 patent drawingFigure 1~2
  • EP3204347B1 patent drawingFigure 3~4
  • EP3204347B1 patent drawingFigure 5~6

AI summary

The present invention describes non-cyclic enaminoketone compounds and their applications relating to absorption electromagnetic energy, in particular UV radiation.