Copolymerizable Azo Compounds for Stable Ophthalmic Lens Light Absorption

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Solution Overview

Problem

Current visible light absorbers for ophthalmic lenses may migrate, phase separate, or leach out, leading to toxicological issues and reduced light-blocking activity, and there is a need for compounds that are copolymerizable, inexpensive to synthesize, and efficient in absorbing light between 380 - 495 nm.

Innovation Solution

Development of novel azo compounds with reactive groups for covalent attachment to ophthalmic lens materials, synthesized in 2-3 steps from inexpensive starting materials, which are suitable for use in intraocular lenses and other ophthalmic devices, allowing for stable light absorption within the desired spectrum.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If visible light absorbers are physically entrapped in lens material, then ease of incorporation is improved, but stability and prevention of migration/leaching deteriorates

Engineering Contradiction:
Improveease of incorporationVSAvoidstability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent combines the light-absorbing function with the polymer network structure by covalently bonding absorber molecules to polymeric chains. This merging of functions ensures the absorber becomes an integral part of the lens material, preventing migration and leaching while maintaining ease of incorporation through copolymerization processes.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The absorber molecules are covalently attached to polymeric chains before final lens assembly, ensuring stability is established in advance. This preliminary covalent bonding prevents subsequent migration or phase separation during lens fabrication and implantation procedures.

Inventive Principle:
Principle #10Preliminary action

2Reliability

If absorbers are covalently bound to polymeric network, then stability and prevention of leaching is improved, but complexity of synthesis deteriorates

Engineering Contradiction:
ImprovestabilityVSAvoidcomplexity of synthesis
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs universal reactive groups (acrylate, methacrylate, vinyl) that can participate in standard copolymerization reactions. These multi-functional groups allow the absorber to be incorporated into various polymeric networks using conventional radical polymerization techniques, reducing synthesis complexity while maintaining covalent bonding stability.

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

Solution Approach 2:

The patent modifies the molecular structure of absorbers by incorporating polymerizable functional groups with specific reactive parameters. These parameter changes enable the absorber to participate in free-radical copolymerization under standard conditions, simplifying the overall synthesis process while ensuring stable covalent attachment.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If absorber lacks sufficient solubility in lens material, then ease of handling is improved, but optical clarity deteriorates due to coalescence into domains

Engineering Contradiction:
Improveease of handlingVSAvoidoptical clarity
Core Design Contradiction:
Ease of operationVSIllumination intensity

Solution Approach 1:

The patent introduces polar and nonpolar substituents at specific local positions on the absorber molecule to balance solubility characteristics. This local modification of molecular properties enables the absorber to dissolve uniformly in the hydrophobic polymeric lens material without coalescing into light-scattering domains, maintaining optical clarity while facilitating handling.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent designs absorber molecules with composite structural features combining hydrophobic aromatic cores and polar functional groups. This composite molecular architecture provides both compatibility with polymeric lens materials and sufficient solubility to prevent phase separation, ensuring optical clarity while maintaining ease of incorporation during fabrication.

Inventive Principle:
Principle #40Composite materials

4Ease of manufacture

If conventional olefinic polymerizable groups are used, then ease of copolymerization is improved, but absorption efficiency in 380-495 nm range deteriorates

Engineering Contradiction:
Improveease of copolymerizationVSAvoidabsorption efficiency
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The patent segments the absorber molecule into distinct functional regions: a light-absorbing chromophore segment (providing 380-495 nm absorption) and a polymerizable functional group segment (enabling copolymerization). This segmentation allows each segment to independently fulfill its function, maintaining both copolymerization ease and absorption efficiency.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent uses the polymerizable functional group as an intermediary that connects the light-absorbing chromophore to the polymeric network. This intermediary group facilitates copolymerization while the chromophore maintains its light-absorbing properties, achieving both ease of incorporation and absorption efficiency in the desired wavelength range.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 azo compounds provide stable and efficient visible light absorption between 380 - 495 nm, preventing migration and leaching, thus ensuring the optical clarity and safety of implantable ophthalmic lenses.

Implementation Method 1

visible light absorbers... efficient in absorbing light between approximately 380 - 495 nm

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentEP2526153B1Visible light absorbers for ophthalmic lens materials
Publication Date: 2014.04.30 NOVARTIS AG
  • EP2526153B1 patent drawingFigure 1
  • EP2526153B1 patent drawingFigure 2
  • EP2526153B1 patent drawingFigure 3

AI summary

Azo compounds that block visible light are disclosed. These light absorbers are particularly suitable for use in intraocular lens materials.