Silicone Compound Oxygen Permeability Copolymer Strength

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Solution Overview

Problem

Current silicone compounds for ophthalmic devices face challenges such as poor compatibility with hydrophilic monomers, insufficient oxygen permeability, mechanical strength, and dimension stability, particularly when used in buffered phosphate solutions, and often result in turbidity or reduced transparency.

Innovation Solution

A silicone compound with a specific structure, featuring a one-ethylene oxide structure, urethane bond, and two (meth)acryl groups, which is well compatible with other polymerizable monomers, including fluorinated substituent group-containing (meth)acryl monomers, and functions as a crosslinking agent to produce a transparent, durable, and oxygen-permeable polymer.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the weight ratio of the Si-containing moiety is increased to improve oxygen permeability, then oxygen permeability is improved, but the mole weight of the polymerizable group becomes large and the strength of the copolymer decreases

Engineering Contradiction:
Improveoxygen permeabilityVSAvoidcopolymer strength
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The invention changes the molecular weight parameter of the polymerizable group within an optimal range (0.5-5 kDa) to balance oxygen permeability and copolymer strength. This parameter optimization allows sufficient Si-containing moiety content for high oxygen permeability while maintaining manageable polymerizable group size for strong copolymers.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining a Si-containing moiety (for oxygen permeability) with a polymerizable group (for copolymerization). This composite approach allows the molecule to simultaneously provide high oxygen permeability through the siloxane units while maintaining copolymer strength through the optimized polymerizable group structure.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional silicone compounds are used to achieve high oxygen permeability, then oxygen permeability is improved, but compatibility with hydrophilic monomers deteriorates resulting in turbidity

Engineering Contradiction:
Improveoxygen permeabilityVSAvoidcompatibility with hydrophilic monomers
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The invention optimizes the molecular weight parameter of the polymerizable group (0.5-5 kDa) to improve compatibility with hydrophilic monomers. This parameter adjustment reduces molecular size and increases flexibility, allowing better mixing and compatibility with hydrophilic monomers while preventing turbidity in the copolymer composition.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If the mole weight of the polymerizable group is increased to improve oxygen permeability, then oxygen permeability is improved, but the strength of the copolymer decreases

Engineering Contradiction:
Improveoxygen permeabilityVSAvoidcopolymer strength
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The invention optimizes the molecular weight parameter of the polymerizable group within the range of 0.5-5 kDa. This parameter optimization ensures that the polymerizable group is large enough to provide sufficient Si-containing moiety for high oxygen permeability, yet small enough to maintain good copolymerization performance and strong copolymer structure.

Inventive Principle:
Principle #35Parameter changes

4Reliability

If conventional preparation methods are used to increase Si-containing moiety content, then oxygen permeability is improved, but many side reactions occur and physical properties of copolymers vary

Engineering Contradiction:
Improveoxygen permeabilityVSAvoidphysical properties consistency
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The invention optimizes the molecular weight parameter of the polymerizable group (0.5-5 kDa) to improve compatibility with hydrophilic monomers and reduce side reactions. This parameter control leads to more consistent copolymerization reactions and more uniform physical properties in the resulting copolymers.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2952515B1Silicone compound and a use therefore
Publication Date: 2017.07.12 SHIN ETSU CHEMICAL CO LTD
  • EP2952515B1 patent drawingFigure 1
  • EP2952515B1 patent drawing
  • EP2952515B1 patent drawing

AI summary

One of the purposes of the present invention is to provide a silicone compound which has a specific number of silicon atoms, is well compatible with (meth)acryl monomers, is suitable as an ophthalmic monomer and provides a polymer having excellent durability of mechanical strength in a buffered phosphate solution. Another purpose of the present invention is to provide a silicone compound which functions well as a crosslinking agent for a polymerizable monomer. Further, another purpose is to provide a method for preparing the silicone compound, in particular the silicone compound having one specific structure at a high ratio. The present invention provides a compound represented by the following formula (2-1): and a method for preparing the silicone compound.