Fluorine Acetophenone Additive for Coating Transparency and Scratch Resistance

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Solution Overview

Problem

Existing surface modifiers, such as silicone and fluorine-containing polymers, fail to provide satisfactory scratch resistance and transparency in coatings due to structural limitations that hinder the full expression of slip and antifouling properties, and the density of fluorine atoms in the coating surface is limited, making it difficult to meet modern performance requirements.

Innovation Solution

A fluorine-containing acetophenone derivative with a poly(perfluoroalkylene ether) chain and a (meth)acryloyl group is introduced using Michael addition reaction, allowing for enhanced surface segregation and bonding of fluorine atoms, thereby improving antifouling, scratch resistance, and slip properties while maintaining coating transparency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If fluorine-containing polymerizable resins with polar groups are used as surface modifiers, then compatibility with fluorine-free curable compounds is ensured, but the density of fluorine atoms in the coating surface is limited and slip properties are reduced

Engineering Contradiction:
ImprovecompatibilityVSAvoiddensity of fluorine atoms
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The patent removes the polar group from the fluorine-containing resin structure, extracting the element that was causing the problem. This allows the fluorine atoms to concentrate at the coating surface without being constrained by polar group interactions, thereby increasing fluorine atom density while maintaining compatibility through the fluorine-free curable compound matrix.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent creates local concentration of fluorine atoms at the coating surface through surface segregation. The fluorine-containing resin migrates to the surface during curing, creating a high-fluorine-density region at the interface while the bulk composition remains controlled. This local accumulation achieves high slip properties without requiring high overall fluorine content throughout the entire coating.

Inventive Principle:
Principle #3Local quality

2Reliability

If fluorine-containing surface modifiers with additional monomer structures are used, then antifouling properties are improved to a degree, but the structural complexity increases and manufacturing precision is reduced

Engineering Contradiction:
Improveantifouling propertiesVSAvoidstructural control
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent segments the fluorine-containing resin into distinct functional components: a fluorine-rich perfluoroalkyl chain segment that provides antifouling and slip properties, and a fluorine-free curable segment that ensures compatibility and controlled polymerization. This segmentation allows independent optimization of each function while simplifying the overall molecular structure for better manufacturing control.

Inventive Principle:
Principle #1Segmentation

3Strength

If silicone-containing surface modifiers are used, then scratch resistance is improved, but transparency of the coating is reduced

Engineering Contradiction:
Improvescratch resistanceVSAvoidtransparency
Core Design Contradiction:
StrengthVSIllumination intensity

Solution Approach 1:

The patent changes the chemical composition parameter by replacing silicone-based surface modifiers with fluorine-based surface modifiers. Fluorine-containing compounds provide scratch resistance through surface hardness and chemical inertness while maintaining optical clarity, unlike silicone modifiers that create hazy or opaque surfaces. This parameter change achieves both scratch resistance and transparency simultaneously.

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 fluorine-containing acetophenone derivative significantly enhances antifouling and scratch resistance properties, maintains coating transparency, and ensures long-term performance by segregating fluorine atoms to the surface and bonding strongly with other curable components, addressing the limitations of previous surface modifiers.

Implementation Method 1

a fluorine-containing acetophenone derivative which may be added to a curable composition to impart excellent antifouling properties, slip properties and scratch resistance to the surface of a cured product obtained from the composition

Methodology Applied
Scientific EffectPhotocleavage: Photodissociation

Implementation Method 2

an active energy ray curable composition which includes a silicone compound having a radically polymerizable unsaturated group in the molecule

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS10961405B2Fluorine-containing acetophenone derivative, fluroine based additive, curable composition including same, and cured product thereof
Publication Date: 2021.03.30 DIC CORP
  • US10961405B2 patent drawing
  • US10961405B2 patent drawing
  • US10961405B2 patent drawing

AI summary

The invention provides a fluorine-containing acetophenone derivative which is useful as an additive that can impart excellent antifouling properties and scratch resistance to the surface of a cured coating and that also offers high transparency of the coating; a fluoroadditive and an active energy ray curable composition which each include the above derivative; a cured product of the composition; and an article having a cured coating of the composition. Specifically, this object is achieved by using a fluorine-containing acetophenone derivative, typically represented by the structural formula below, that is obtained by introducing an acryloyl group into a poly(perfluoroalkylene ether) chain and thereafter introducing, using Michael addition reaction, an α-aminoacetophenone-based structural unit capable of generating radical species by photocleavage