Perfluoropolyether Acrylate for Hard Coat Compatibility

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Solution Overview

Problem

Photo-curable fluorine compounds with perfluoropolyether groups face compatibility issues with non-fluorine organic compounds, limiting their blending capabilities and usage due to poor compatibility with photo polymerization initiators and solvents, and compounds with fewer than eight carbon atoms in their perfluoroalkyl groups exhibit inferior surface properties.

Innovation Solution

A perfluoropolyether group-containing acrylate compound with a specific molecular structure, allowing for better compatibility with non-fluorinated organic compounds and maintaining water- and oil-repellent properties, is developed. This compound is synthesized through an addition reaction involving a perfluoropolyether compound and a cyclic hydrogen siloxane, followed by hydrosilylation and reaction with olefin compounds, forming a cured product suitable for hard coat applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a perfluoropolyether group-containing acrylate compound is used to provide water- and oil-repellency, then surface properties are improved, but compatibility with non-fluorine organic compounds deteriorates

Engineering Contradiction:
Improvesurface propertyVSAvoidcompatibility with non-fluorine organic compounds
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent introduces a specific molecular structure where perfluoropolyether groups are localized in the side chains rather than distributed throughout the main chain. This local concentration of fluorine atoms provides water- and oil-repellency at the surface while the main chain maintains compatibility with non-fluorine organic compounds through its hydrocarbon structure.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The acrylate compound combines two distinct structural elements: a hydrocarbon-based main chain (providing compatibility with non-fluorine organic compounds) and perfluoropolyether side chains (providing water- and oil-repellency). This composite structure allows the molecule to simultaneously achieve both compatibility and surface performance.

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If a perfluoroalkyl group with less than eight carbon atoms is used, then environmental regulations are satisfied, but surface properties deteriorate

Engineering Contradiction:
Improveenvironmental complianceVSAvoidsurface property
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent changes the structural parameter from simple perfluoroalkyl groups to perfluoropolyether groups with ether bonds incorporated. This structural modification allows the compound to maintain effective surface properties while using fewer than eight carbon atoms in the perfluoroalkyl portion, thus satisfying environmental regulations.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The ether bonds act as intermediaries within the perfluoropolyether group, modifying the electronic and steric properties of the fluorinated chain. This intermediary structure enables the compound to achieve effective surface performance with reduced carbon atom count, bridging the gap between environmental compliance and performance requirements.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If a urethane acrylate with fluorine-containing polyether diol is used, then water- and oil-repellency is achieved, but compatibility with photo polymerization initiators and non-fluorinated organic solvents deteriorates

Engineering Contradiction:
Improvewater- and oil-repellencyVSAvoidcompatibility with photo polymerization initiators and solvents
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent places perfluoropolyether groups specifically in the side chains of the acrylate molecule, concentrating the water- and oil-repellent properties in localized regions. The main chain remains composed of hydrocarbon structures that maintain compatibility with photo polymerization initiators and non-fluorinated organic solvents.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The molecule combines hydrocarbon-based main chain structures (providing compatibility with initiators and solvents) with perfluoropolyether side chains (providing water- and oil-repellency). This composite architecture enables simultaneous achievement of both compatibility and surface performance.

Inventive Principle:
Principle #40Composite materials

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 resulting acrylate compound demonstrates improved compatibility with non-fluorinated organic compounds, enabling effective curing and providing enhanced water- and oil-repellent properties, making it suitable for use in hard coat formulations with stain resistance, fingerprint resistance, and improved surface properties.

Implementation Method 1

photo-curable fluorine compound which has good compatibility with non-fluorine organic compounds

Methodology Applied
Scientific EffectPhoto-polymerization: Photopolymerisation

Data Source

PatentUS8283480B2Perfluoropolyether group-containing acrylate compound
Publication Date: 2012.10.09 SHIN ETSU CHEMICAL CO LTD
  • US8283480B2 patent drawing
  • US8283480B2 patent drawing
  • US8283480B2 patent drawing

AI summary

The present invention relates to a photo-curable perfluoropolyether group-containing acrylate compound represented by the following formula (1):X1—[Z—Rf—Z—X2]v—Z—Rf—Z—X1  (1)wherein Rf is a divalent perfluoropolyether group;X1 is a group represented by the following formula (2):R2 is a group represented by the following formula (4):X2 is a group represented by the following formula (5):and Z is a divalent organic group.