Polyfunctional Epoxy Organosilicon Adhesion

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Solution Overview

Problem

Conventional silane coupling agents have limited epoxy groups per alkoxysilyl group, restricting their reactivity with organic resins and adhesion capabilities to inorganic materials.

Innovation Solution

Synthesis of polyfunctional epoxy-containing organosilicon compounds by combining polyglycidyl ether compounds with silane coupling agents having isocyanate groups, allowing for a variable ratio of epoxy groups to alkoxysilyl groups and forming bonds with organic resins and inorganic materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional silane coupling agents with limited epoxy groups per alkoxysilyl group are used, then the molecular structure is simple and easy to manufacture, but the reactivity with organic resins and adhesion capabilities to inorganic materials are restricted

Engineering Contradiction:
Improveease of manufactureVSAvoidadhesion capabilities
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention creates a composite molecular structure combining polyglycidyl ether compounds (providing multiple epoxy groups) with silane coupling agents (providing alkoxysilyl groups). This composite approach allows the molecule to simultaneously offer multiple reactive epoxy groups for organic resin crosslinking and hydrolyzable alkoxysilyl groups for inorganic substrate bonding, thereby enhancing adhesion capabilities while maintaining manufacturability through established chemical synthesis routes.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The polyfunctional epoxy-containing organosilicon compound serves multiple functions within a single molecular structure: it acts as both a crosslinking agent (through multiple epoxy groups reacting with organic resins) and a coupling agent (through hydrolyzable alkoxysilyl groups bonding to inorganic materials). This multi-functionality resolves the contradiction by enabling enhanced adhesion capabilities without requiring multiple separate compounds, thus maintaining ease of manufacture and application.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Reliability

If polyfunctional epoxy-containing organosilicon compounds with multiple epoxy groups per alkoxysilyl group are synthesized, then the reactivity with organic resins and adhesion to inorganic materials is enhanced, but the molecular design and synthesis complexity increases

Engineering Contradiction:
Improvebond strengthVSAvoidmolecular design complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The molecular design is segmented into distinct functional modules: a polyglycidyl ether core providing multiple epoxy groups and silane coupling agent moieties providing alkoxysilyl groups. This segmentation allows each module to perform its specific function independently while contributing to the overall enhanced bond strength, thereby managing molecular design complexity through modular architecture rather than attempting to design a completely new complex molecule from scratch.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention uses the polyglycidyl ether compound as an intermediary molecule that bridges the gap between simple silane coupling agents and the desired polyfunctional product. By reacting the hydroxyl groups of polyglycidyl ether with isocyanate groups of silane coupling agents, the intermediary approach enables controlled synthesis of the target compound with multiple epoxy groups, managing synthesis complexity through a stepwise chemical transformation rather than direct synthesis.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If the ratio of epoxy groups to alkoxysilyl groups is increased, then the reactivity with organic resins is enhanced, but the balance between organic and inorganic reactivity may be disrupted

Engineering Contradiction:
Improvereactivity with organic resinVSAvoidreactivity balance
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The invention employs parameter changes by systematically varying the ratio of epoxy groups to alkoxysilyl groups in the molecular structure. By adjusting this compositional parameter, the compound can be optimized for different applications: higher epoxy-to-silane ratios enhance reactivity with organic resins for improved crosslinking density, while maintaining sufficient alkoxysilyl groups ensures adequate bonding to inorganic substrates. This parameter optimization resolves the contradiction by allowing tailoring of reactivity balance according to specific application requirements.

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

Enhanced bond strength and adhesion improvements with organic resins, inorganic fillers, and metal substrates, surpassing conventional epoxy silane coupling agents by providing multiple reactive sites.

Implementation Method 1

combining a polyglycidyl ether compound having a plurality of epoxy groups and a hydroxyl group in the molecule with a silane coupling agent having an isocyanate group such that the hydroxyl group on the polyglycidyl ether compound may react with the isocyanate group on the silane coupling agent

Methodology Applied
Scientific EffectChemical bonding (urethane formation): Chemical Bonding

Implementation Method 2

hydrolyzable silyl groups

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS8207259B2Polyfunctional epoxy-containing organosilicon compound, making method, coating composition, and coated article
Publication Date: 2012.06.26 SHIN ETSU CHEMICAL CO LTD
  • US8207259B2 patent drawing
  • US8207259B2 patent drawing
  • US8207259B2 patent drawing

AI summary

A polyglycidyl ether compound having a plurality of epoxy groups and a hydroxy group in the molecule is reacted with a silane coupling agent having an isocyanate group, and specifically the hydroxyl group on the polyglycidyl ether compound is reacted with the isocyanate group on the silane coupling agent. Then an organosilicon compound having a plurality of epoxy groups per alkoxysilyl group is synthesized wherein the ratio of epoxy groups to alkoxysilyl groups may be adjusted as desired. The resulting organosilicon compound is useful as a primer and resin modifier.