Nitrogen-Bonded Silicone Compound for Oxygen Permeability
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Solution Overview
Problem
Silicone compounds with radical-polymerizable groups, such as 3-[tris(trimethylsiloxy)silyl]propyl acrylamide (TRIS-A), have poor handling properties at room temperature due to their solid state and limited compatibility with hydrophilic monomers, which affects their reactivity and oxygen permeability in contact lens materials.
Innovation Solution
A silicone compound with a radical-polymerizable group bound to a siloxane chain via a nitrogen atom, ensuring the compound remains liquid at room temperature and enhances compatibility and reactivity, formulated as R--Si--O--Si--N--R', where R is a hydrogen or methyl group, and the siloxane chain has 2 to 20 silicon atoms, allowing for improved oxygen permeability and handling.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If a polymerizable silicone compound such as TRIS-A is used to improve oxygen permeability, then oxygen permeability is improved, but handling properties deteriorate because the compound is solid at room temperature
Solution Approach 1:
The invention changes the physical state parameter of the silicone compound from solid to liquid at room temperature by modifying the molecular structure. Specifically, it uses a silicone compound with a polymerizable group that has a lower melting point, transforming it from a solid (TRIS-A with melting point ~50°C) to a liquid state, thereby improving handling properties while maintaining oxygen permeability
Solution Approach 2:
The invention creates a composite monomer system by combining the polymerizable silicone compound with a hydrophilic monomer. This composite approach allows the silicone component to provide oxygen permeability while the hydrophilic monomer ensures compatibility and liquid state at room temperature, resolving the contradiction between oxygen permeability and handling properties
2Reliability
If a polymerizable silicone compound is used to improve oxygen permeability, then oxygen permeability is improved, but compatibility with hydrophilic monomers deteriorates
Solution Approach 1:
The invention uses a composite monomer system where a polymerizable silicone compound is combined with a hydrophilic monomer. The silicone component (containing Si-O-Si bonds) provides oxygen permeability, while the hydrophilic monomer component ensures compatibility between the monomers. This composite approach resolves the contradiction by allowing both oxygen permeability and compatibility to coexist in the copolymer system
Solution Approach 2:
The invention applies local quality by introducing different functional groups at different parts of the monomer structure. The silicone-containing portion provides oxygen permeability locally, while the hydrophilic portion provides compatibility locally. This spatial separation of functions allows the material to simultaneously achieve both oxygen permeability and monomer compatibility
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 silicone compound maintains excellent oxygen permeability and reactivity, providing a cured product with enhanced compatibility and handling properties, outperforming traditional compounds like TRIS-A by being liquid at room temperature and demonstrating better curability and compatibility with other monomers.
Implementation Method 1
a polymerizable group and a siloxane chain which is bound to the polymerizable group via a nitrogen atom, thereby providing a cured product having excellent compatibility and handling properties
Data Source
AI summary
The present invention provides a radical-polymerizable group-containing silicone compound which is liquid at room temperature and has good handling properties, has excellent reactivity and provides a cured product having an excellent oxygen permeability. Thus, the present invention provides a silicone compound represented by the following formula (1): wherein A is, independently of each other, a substituted or unsubstituted, linear or branched, divalent hydrocarbon group having 1 to 6 carbon atoms; B is, independently of each other, a monovalent organosilicone residue having 2 to 20 silicon atoms; and X is a monovalent radical-polymerizable group or a monovalent group comprising said monovalent radical-polymerizable group. Further, the present invention provides a method for preparing the silicone compound.