Organosilicon Coupling Compound for Cyclic Polymerization Adhesion

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Solution Overview

Problem

Conventional silane coupling agents with polymerizable groups lack sufficient adherence to various substrates, and there are no reported examples of silane coupling agents with both an alkenyl ether moiety and an acryloyl group on the same molecule that exhibit cyclic polymerizability.

Innovation Solution

Development of an organosilicon compound with a hydrolyzable silyl group, an alkenyl ether moiety, and an acryloyl group, prepared by reacting a halogen group-containing organosilicon compound with a metal salt compound, which can be used in curable compositions to enhance adherence to substrates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional polymerizable group-containing silane coupling agents are used, then the composition can be cured through polymerization, but the adherence to various substrates is insufficient

Engineering Contradiction:
Improveadherence to substratesVSAvoidsubstrate compatibility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent changes the chemical structure parameters of the silane coupling agent by introducing a specific α-substituent (other than methyl group) at the α-position of the acryloyl or methacryloyl group. This structural modification enables cyclic polymerization mechanism, which significantly improves adherence to various substrates while maintaining polymerizability and curing properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite molecular structure that combines multiple functional moieties: a hydrolyzable silyl group for inorganic substrate bonding, an alkenyl ether moiety for cyclic polymerization, and an acryloyl/methacryloyl group for radical polymerization. This composite structure enables the silane coupling agent to simultaneously achieve excellent adherence, polymerizability, and curing properties.

Inventive Principle:
Principle #40Composite materials

2Reliability

If silane coupling agents with standard α-substituents (methyl group) are used, then the compound structure is simple and well-established, but cyclic polymerizability and excellent adherence are not achieved

Engineering Contradiction:
Improvecyclic polymerizabilityVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the α-substituent parameter at the α-position of the acryloyl or methacryloyl group, selecting specific groups (other than methyl) that enable cyclic polymerization. This parameter change introduces cyclic polymerizability while maintaining reasonable molecular structure complexity for practical application.

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 organosilicon compound improves the adherence of cured products to various substrates, making them suitable for use as coating agents and adhesives.

Implementation Method 1

preparing the compound by reacting a halogen group-containing organosilicon compound with a metal salt compound

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

a silicon atom-bonded hydrolyzable group

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 3

these compounds undergo cyclic polymerization via a radical polymerization mechanism

Methodology Applied
Scientific EffectRadical polymerization: Photopolymerisation

Data Source

PatentEP4282653B1Organosilicon compound, production method therefor, and curable composition
Publication Date: 2026.02.25 SHIN ETSU CHEMICAL CO LTD
  • EP4282653B1 patent drawing
  • EP4282653B1 patent drawing
  • EP4282653B1 patent drawing

AI summary

An organosilicon compound represented by formula (1). (R1 is an alkyl, alkenyl, aryl, or acyl group, R2 is an alkyl or aryl group, R3 is a hydrogen atom or a methyl group, A1 is a single bond or an alkylene group, A2, A3, and A4 are each a methylene group or an oxygen atom, with the proviso that at least one of the A2, A3, and A4 moieties is an oxygen atom, and n is an integer of 1-3.)