Benzophenone Polymerizable Dye for Foldable Intraocular Lenses
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Solution Overview
Problem
Conventional ophthalmic lens materials, such as polymethyl methacrylate, allow UV rays and blue light to pass through, causing dazzling and potential retina damage, and benzophenone-type UV-absorbable dyes used in soft foldable intraocular lenses become hard when used in large quantities, hindering lens insertion and reducing yield due to byproduct formation during production.
Innovation Solution
A novel benzophenone-type polymerizable dye containing a urethane bond, synthesized by reacting specific compounds with a polymerizable group, which absorbs UV and visible light in the 380-500 nm range, maintaining flexibility and preventing polymerization suppression, even when used in foldable intraocular lenses.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If conventional benzophenone-type UV-absorbable dyes are used in soft foldable intraocular lenses, then UV protection is provided, but the lens becomes hard and loses flexibility
Solution Approach 1:
The invention changes the chemical structure parameters of the benzophenone dye by introducing a urethane group at the 4-position of the phenyl ring. This structural modification allows the dye to maintain UV absorption capability while preventing the hardening effect observed with conventional dyes, thereby preserving lens flexibility even at high dye concentrations (0.01-1.0% by weight).
Solution Approach 2:
The invention creates a composite molecular structure combining benzophenone chromophore with a urethane group containing polymerizable functionality. This composite structure integrates UV absorption properties with flexibility-maintaining characteristics, allowing the dye molecule itself to contribute to both protection and softness of the lens material.
2Object-affected harmful factors
If conventional benzophenone dyes are used in large amounts, then UV absorption is improved, but lens flexibility deteriorates
Solution Approach 1:
By modifying the chemical structure to include a urethane group with specific parameters (m=0-18, n=0-18), the invention enables high UV absorption at 0.01-1.0% dye concentration while maintaining lens flexibility. The urethane linkage provides molecular flexibility that prevents hardening even at maximum dye loading, facilitating surgical insertion of foldable lenses.
3Productivity
If UV-PEP is reacted with methacrylic acid, then polymerizable dye is produced, but yield is reduced due to byproduct formation
Solution Approach 1:
The invention uses an isocyanate compound as an intermediary reagent to react with UV-PEP. The isocyanate group (-NCO) selectively reacts with the primary hydroxyl group of UV-PEP to form a urethane linkage, avoiding reaction with phenolic hydroxyl groups. This intermediary approach eliminates byproduct formation and achieves high yields (80-95%) of the desired polymerizable dye.
Solution Approach 2:
The invention extracts and utilizes only the primary hydroxyl group of UV-PEP for reaction with the isocyanate compound, leaving the phenolic hydroxyl groups untouched. This selective extraction of the reactive site prevents unwanted side reactions and byproduct formation, significantly improving production efficiency.
4Ease of manufacture
If conventional lens materials are used, then manufacturing is simplified, but UV protection and blue light filtering are insufficient
Solution Approach 1:
The invention merges the UV absorption function with the lens material itself by incorporating polymerizable benzophenone dyes directly into the polymer matrix. This combination eliminates the need for separate UV-coating layers or additional manufacturing steps, while providing comprehensive protection against UV rays and blue light (380-500 nm) throughout the entire lens structure.
Solution Approach 2:
The invention creates a composite ophthalmic lens material combining polymeric base material with polymerizable benzophenone dye molecules. This composite structure integrates mechanical properties of the polymer with UV absorption capabilities of the benzophenone chromophore, achieving both ease of manufacture and superior UV protection in a single material system.
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 new dye provides excellent light resistance and chemical stability, maintaining lens flexibility and preventing elution, while improving yield and simplifying purification, thus offering a safer and more effective ophthalmic lens material with enhanced UV protection.
Implementation Method 1
a benzophenone type polymerizable dye which absorbs an UV ray and visible lights in a blue range of about 380 to 500 nm
Data Source
AI summary
A novel benzophenone type polymerizable dye containing a urethane bond and an ophthalmic lens containing the said polymerizable dye are disclosed. The benzophenone type polymerizable dye is shown by the following general formula (1)(wherein R1 and R2 are respectively and independently a hydrogen atom, a hydroxyl group, a carboxylic group, a C1 to C8 alkyl group, a C1 to C8 alkoxy group, a sulfonic acid group or a benzyloxy group, and m and n are respectively and independently an integer of 0 to 18. R3 is any of a polymerizable functional group of a vinyl group, an acryloyl group or a methacryloyl group).