Fluorinated Urethane Silane Coatings for Metal Oxide Adhesion

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Solution Overview

Problem

Existing compounds do not effectively improve adhesion to metal oxide-containing surfaces.

Innovation Solution

Development of urethane compounds comprising a perfluorinated group, a hydrolysable silane group, and a (meth)acryl group, formed through a Michael addition reaction, which are applied as a polymerizable composition to enhance adhesion to metal oxide surfaces.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If conventional fluorinated compounds are used, then adhesion to metal oxide surfaces is improved, but coating performance and bonding effectiveness remain inadequate

Engineering Contradiction:
Improveadhesion strengthVSAvoidcoating performance
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent employs composite material design by integrating three distinct functional groups into a single molecule: perfluorinated groups for metal oxide adhesion, silane groups for crosslinking and bonding, and (meth)acryl groups for polymerization. This composite structure enables the compound to simultaneously provide strong adhesion to metal oxide surfaces, form durable crosslinked networks, and achieve reliable coating performance that conventional single-function fluorinated compounds cannot deliver.

Inventive Principle:
Principle #40Composite materials

2Area of stationary object

If complex nanostructured patterns are coated, then surface coverage is improved, but coating continuity and defect reduction become challenging

Engineering Contradiction:
Improvesurface coverageVSAvoidcoating continuity
Core Design Contradiction:
Area of stationary objectVSManufacturing precision

Solution Approach 1:

The patent utilizes parameter changes through the curing process where (meth)acryl groups undergo polymerization upon exposure to UV light or other initiators. This transformation from liquid monomer/oligomer state to solid polymer network enables the coating to flow and conform to complex nanostructured surfaces during application, then lock into continuous coverage upon curing, eliminating defects like bubbles and ensuring uniform coating across challenging geometries.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The silane groups act as intermediaries that facilitate bonding between the organic polymer matrix and inorganic metal oxide substrates. The hydrolysable silane groups react with surface hydroxyl groups on metal oxides to form strong covalent Si-O-Metal bonds, while the organic portions integrate into the polymer network. This intermediary mechanism ensures continuous, defect-free coating on complex nanostructured patterns by creating a robust bridge between dissimilar materials.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 compounds provide improved adhesion to metal oxide surfaces, enabling the formation of continuous coatings without defects on nanostructured surfaces and facilitating the formation of etched nano-scale patterns.

Implementation Method 1

a compound is described having the following formula: (Formula 1) wherein Y is a hydrolysable group

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

a mixture of compounds is described comprising the reaction product of i) a urethane compound comprising a perfluorooxyalkyl moiety and at least two (meth)acryl groups; and ii) a silane compound comprising hydrolysable groups

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 3

a method of making a cured composition is described comprising providing a polymerizable composition comprising the compound or mixture of compounds as described herein; and curing the (meth)acryl groups

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS12617970B2Urethane compounds comprising perfluorinated group, hydrolysable silane group, and (meth)acryl group
Publication Date: 2026.05.05 3M INNOVATIVE PROPERTIES CO
  • US12617970B2 patent drawing
  • US12617970B2 patent drawing
  • US12617970B2 patent drawing

AI summary

A compound is described having following formula: (I) Also described is a mixture of compounds comprising the reaction product of i) a urethane compound comprising a perfluorooxyalkyl moiety and at least two (meth)acryl groups; and ii) a silane compound comprising hydrolysable groups and a group selected from amine or mercapto group; wherein i) and ii) are reacted at an equivalent ratio of excess compound i) such that (meth)acryl groups remain unreacted. Methods and articles are also described.