Fluorinated Coupling Agent Adhesion Mechanism

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

The industry faces challenges in achieving effective adhesion of fluorinated free-radically polymerizable materials, as existing coupling agents do not adequately address this issue.

Innovation Solution

A polymerizable composition comprising a fluorinated monomer or oligomer combined with a coupling agent featuring a (meth)acryl terminal group, a terminal silane with hydrolysable groups, and a perfluorooxyalkylene or perfluorooxyalkyl moiety, which includes compounds with specific formulas and reaction products to enhance adhesion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If conventional coupling agents are used with fluorinated monomers, then polymerization can proceed, but adhesion of the cured material is insufficient

Engineering Contradiction:
ImproveadhesionVSAvoidbond stability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The coupling agent combines multiple functional groups into a single molecule: (meth)acryl terminal groups for polymerization, silane groups with hydrolysable moieties for substrate bonding, and perfluorooxyalkylene/perfluorooxyalkyl groups for compatibility with fluorinated polymers. This composite structure enables simultaneous achievement of polymerization reactivity and adhesion strength.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The coupling agent acts as an intermediary substance between the fluorinated polymer and the substrate. The perfluorooxyalkylene/perfluorooxyalkyl groups provide compatibility with fluorinated polymers, the silane groups bond to the substrate, and the (meth)acryl groups enable polymerization, thus mediating the bond between dissimilar materials.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Adaptability or versatility

If fluorinated content of the coupling agent is increased to improve compatibility, then polymerization reactivity decreases

Engineering Contradiction:
Improvecompatibility with fluorinated polymerVSAvoidpolymerization reactivity
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

Different parts of the coupling agent molecule have different functions: the perfluorooxyalkylene/perfluorooxyalkyl groups provide local compatibility with fluorinated polymers, the (meth)acryl terminal groups provide local polymerization reactivity, and the silane groups provide local substrate bonding capability. This local differentiation allows the molecule to excel at multiple functions simultaneously.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The coupling agent uses specific parameter ranges: perfluorooxyalkylene groups with 2-6 perfluorinated carbon atoms, perfluoropolyether units with 2-25 repeating units, and controlled ratios of fluorinated content (2-20 wt%). These parameter optimizations balance compatibility and reactivity.

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 described solution improves the adhesion of cured fluorinated materials, forming a stable and effective bond, particularly suitable for use in fluorinated free-radically polymerizable compositions.

Implementation Method 1

a terminal silane comprising hydrolysable groups

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

a terminal silane comprising hydrolysable groups

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 3

fluorinated free-radically polymerizable materials

Methodology Applied
Scientific EffectFree-radical polymerization: Photopolymerisation

Implementation Method 4

improve adhesion of fluorinated free-radically polymerizable materials

Methodology Applied
Scientific EffectFluorophilic interaction: Absorption (physical)

Data Source

PatentUS20230151149A1Polymerizable Compositions and Compounds Comprising Perfluorinated Group, Hydrolysable Silane Group, and (Meth)Acryl Group
Publication Date: 2023.05.18 3M INNOVATIVE PROPERTIES CO
  • US20230151149A1 patent drawing
  • US20230151149A1 patent drawing
  • US20230151149A1 patent drawing

AI summary

A polymerizable composition is described comprising a fluorinated monomer, oligomer, or mixture thereof; and a coupling agent comprising a (meth)acryl terminal group, a terminal silane comprising hydrolysable groups and a perfluorooxyalkylene or perfluorooxyalkyl moiety. Also described are compounds and methods.