Fluorinated Ether Synthesis for High-Yield Surface Coatings
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Solution Overview
Problem
Existing fluorinated ether compounds used for surface treatment lack sufficient abrasion resistance and lubricity, and the processes for producing fluorinated ether compounds with hydrolyzable silyl groups do not provide high yields or clear methods for obtaining intermediate compounds.
Innovation Solution
A process involving the reaction of specific fluorinated ether compounds with diallylamine to produce compounds that can be further reacted with trimethoxysilane, resulting in fluorinated ether compounds with improved water/oil repellency, abrasion resistance, and fingerprint stain removability, using a liquid medium and specific reaction conditions to achieve high yields.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If fluorinated ether compounds are used for surface treatment, then water/oil repellency is improved, but abrasion resistance and lubricity are insufficient
Solution Approach 1:
The invention uses composite fluorinated ether compounds that combine multiple functional groups (silyl groups, carboxyl groups, and fluorinated ether chains) into a single molecule. This composite structure allows the compound to simultaneously provide water/oil repellency through the fluorinated ether portion while maintaining abrasion resistance through the silyl group that forms strong bonds with the substrate surface.
Solution Approach 2:
The invention introduces different functional groups at specific positions within the fluorinated ether compound molecule. The silyl group is positioned to interact with the substrate surface for abrasion resistance, while the fluorinated ether chain extends outward to provide water/oil repellency. This local differentiation of functional properties within the single compound resolves the contradiction between repellency and durability.
2Object-affected harmful factors
If fluorinated ether compounds with hydrolyzable silyl groups are used, then fingerprint stain removability is improved, but production yield is insufficient
Solution Approach 1:
The invention uses compound (12) as an intermediate compound in a two-step synthesis process. This intermediate contains the fluorinated ether chain and carboxyl group, which then reacts with trimethoxysilane to form the final compound with the hydrolyzable silyl group. This intermediary approach allows for high-yield production by optimizing each step separately and avoiding direct synthesis of the final complex molecule.
Solution Approach 2:
The synthesis process is divided into separate stages: first forming the fluorinated ether chain with carboxyl groups, then adding the silyl groups in a second step. This segmentation of the synthesis process into discrete, optimized steps improves overall production yield while maintaining the fingerprint stain removability provided by the hydrolyzable silyl groups.
3Object-affected harmful factors
If existing fluorinated ether compounds are used for hard coat layers, then oil-based ink repellency is improved, but lubricity is insufficient
Solution Approach 1:
The invention modifies the molecular structure parameters of the fluorinated ether compound by incorporating both the fluorinated ether chain (for ink repellency) and the silyl group with hydrolyzable functionality (for lubricity). This parameter change in the molecular composition allows the single compound to provide both oil-based ink repellency and improved lubricity properties.
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 produced fluorinated ether compounds effectively impart excellent water/oil repellency, abrasion resistance, and fingerprint stain removability to substrate surfaces and hard coat layers, with improved properties and high production yields.
Implementation Method 1
reacting a compound represented by the following formula (3) or a compound represented by the following formula (4) with a compound represented by the following formula (5) to obtain a compound represented by the following formula (2)
Implementation Method 2
reacting compound (2) with trimethoxysilane to obtain compound (1)
Implementation Method 3
a fluorinated ether compound having a poly(oxyperfluoroalkylene) chain, wherein an ether bond (-O-) is present in the perfluoroalkylene chain, can particularly impart excellent fat and oil stain removability
Implementation Method 4
an anti-fingerprint agent which imparts fingerprint stain removability to a substrate surface... containing a fluorinated ether compound having a hydrolyzable silyl group
Data Source
AI summary
Processes for producing a fluorinated ether compound are provided by which fluorinated ether compound capable of imparting excellent water/oil repellency, to a substrate surface or a hard coat layer can be easily produced in high yield. A process comprising reacting Rf(CF2)a-CF2OC(=O)Rf4 or Rf(CF2)a-C(=O)X1 with HN(-R1CH=CH2)2 to obtain Rf(CF2)a-C(=)N(-R1CH2=CH2)2 and a process comprising obtaining the above product and reacting the product with OHSiR2nL3-n to obtain Rf(CF2)a-C(=O)N(-R1CH2CH2SiR2nL3-n)2 wherein Rf is a linear polyfluoroalkyl group having at least two carbon atoms and at least one etheric oxygen atom between carbon atoms, Rf4 is a C1-30 perfluoroalkyl group or the like, X1 is a halogen atom, R1 is an alkylene group, a is an integer of from 1 to 5, R2 is a monovalent hydrocarbon group, L is a hydrolyzable group, and n is an integer of from 0 to 2.