Tertiary-Hydroxyl Siloxane Monomer for Hydrophilic Medical Hydrogels

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Solution Overview

Problem

Conventional siloxane compounds with primary or secondary hydroxyl groups cause undesirable crosslinked structures and reduced hydrophilicity when used in medical materials, leading to increased hardness and decreased compatibility with hydrophilic monomers.

Innovation Solution

A (poly)siloxane monomer with a (poly)siloxane structure and a tertiary hydroxyl group at the linkage to a polymerizable group, enhancing compatibility with hydrophilic monomers and preventing crosslinked structures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a siloxane compound with primary or secondary hydroxyl group is used, then the compound can be prepared, but it causes crosslinked structure formation and decreased hydrophilicity in the resulting medical material

Engineering Contradiction:
ImprovehydrophilicityVSAvoidcrosslinked structure formation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical parameter of the hydroxyl group from primary or secondary to tertiary. This parameter change prevents the harmful crosslinked structure formation while maintaining hydrophilicity, as the tertiary hydroxyl group does not react with radicals to form crosslinks like primary or secondary hydroxyl groups do.

Inventive Principle:
Principle #35Parameter changes

2Strength

If a siloxane compound with primary or secondary hydroxyl group is used, then the compound structure can be formed, but the resulting medical material shows increased hardness and decreased hydrophilicity

Engineering Contradiction:
Improvematerial strengthVSAvoidhydrophilicity
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The invention changes the hydroxyl group type parameter to tertiary, which maintains material strength through the siloxane structure while preventing the formation of crosslinked structures that would reduce hydrophilicity. The tertiary hydroxyl group provides the necessary structural integrity without the harmful crosslinking side reactions.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If a siloxane compound with primary or secondary hydroxyl group is used, then the compound can be synthesized, but it shows poor compatibility with hydrophilic monomers

Engineering Contradiction:
Improvecompatibility with hydrophilic monomerVSAvoidphase separation
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The invention changes the hydroxyl group parameter to tertiary, which improves compatibility with hydrophilic monomers by preventing phase separation. The tertiary hydroxyl group does not cause the hydrophobic siloxane and hydrophilic monomer to separate into different phases, enabling homogeneous copolymerization.

Inventive Principle:
Principle #35Parameter changes

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 siloxane monomer achieves a copolymer with improved strength and hydrophilicity, resulting in transparent and transparent hydrogels suitable for medical materials.

Implementation Method 1

a radical may bond to the hydroxyl group of the compound to form a hydroxy radical which may cause crosslinked structure

Methodology Applied
Scientific EffectRadical reaction prevention:

Data Source

PatentEP3981802B1Siloxane and method for producing same
Publication Date: 2025.08.13 SHIN ETSU CHEMICAL CO LTD
  • EP3981802B1 patent drawing
  • EP3981802B1 patent drawing
  • EP3981802B1 patent drawing

AI summary

The purpose of the present invention is to provide a siloxane suitable for preparing a medical material, and a method for preparing the compound. The present invention provides a siloxane represented by the formula (1), wherein R1 is a hydrogen atom or a methyl group, R2 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, L is a divalent hydrocarbon group which has 2 to 10 carbon atoms and may have one or more ether bonds, and A is a (poly)siloxane group represented by the formula (2) or (3), wherein n is an integer of 1 to 100, a is an integer of 0 to 10, b is an integer of 0 to 10, and c is an integer of 0 to 10, provided that a+b+c is 2 or more, and R is, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms. The present invention further provides a method for preparing the siloxane, a polymer comprising recurring units derived from the siloxane, and a medical material, particularly an ophthalmic device, comprising the aforesaid polymer.