Amine-Modified Perfluoropolyether Solubility and Durability
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Solution Overview
Problem
Perfluoropolyether compounds with C—O—Si bonds are prone to breakdown in moisture or alcohol, leading to durability issues, and amine-modified compounds with high fluorine content exhibit poor solubility in solvents and resins.
Innovation Solution
Diterminally amine-modified perfluoropolyether compounds are developed, where the perfluoropolyether skeleton is coupled with amine groups through siloxane structures, enhancing solubility and stability, and prepared by reacting diterminally silanol-modified perfluoropolyether compounds with cyclic silazane or amino group-containing organoxysilane compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If perfluoropolyether compounds are coupled with amine groups through tetrafluorophenylene groups, then reactivity and transformation capability are improved, but solubility in solvents and resins deteriorates due to high fluorine content
Solution Approach 1:
The patent introduces a non-fluorinated spacer group (divalent hydrocarbon group) as an intermediary between the perfluoropolyether skeleton and the amine group. This spacer acts as a mediator that reduces the fluorine content in the critical regions, thereby improving solubility while maintaining the reactive amine functionality and transformation capability of the compound.
Solution Approach 2:
The patent applies local quality by creating regions with different fluorine concentrations within the molecule. The perfluoropolyether skeleton maintains high fluorine content for liquid repellency, while the spacer regions have low or zero fluorine content to provide solubility and flexibility, allowing each part of the molecule to fulfill its specific function optimally.
2Ease of manufacture
If perfluoropolyether compounds contain C—O—Si bonds for coupling, then functional group attachment is improved, but durability deteriorates due to bond breakdown in moisture or alcohol
Solution Approach 1:
The patent extracts the problematic C—O—Si bond linkage from the molecular structure and replaces it with a C—C bond through the divalent hydrocarbon spacer. This removal of the hydrolytically unstable bond eliminates the durability issue while preserving the ability to attach functional groups like amine groups to the perfluoropolyether skeleton.
3Reliability
If fluorine content is increased to enhance liquid repellency, then water and oil repellency are improved, but solubility in solvents and resins deteriorates
Solution Approach 1:
The patent segments the molecule into distinct functional regions: a perfluoropolyether segment for liquid repellency, a non-fluorinated hydrocarbon spacer segment for solubility, and functional group segments for reactivity. This segmentation allows each segment to contribute its specific property without the negative effects of the other segments, achieving a balance between repellency and solubility.
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 diterminally amine-modified perfluoropolyether compounds demonstrate excellent solubility in various solvents and reactive resins, and the resulting compositions exhibit superior liquid repellency due to the perfluoropolyether groups, leading to improved durability and performance in coated substrates.
Implementation Method 1
diterminally amine-modified perfluoropolyether compounds in which a perfluoropolyether skeleton and amine groups are coupled through siloxane structures
Implementation Method 2
preparing such compounds by reacting a diterminally silanol-modified perfluoropolyether compound with a cyclic silazane or an amino group-containing organoxysilane compound
Implementation Method 3
have a very small surface free energy due to the effect of the many fluorine atoms included on the perfluoropolyether group, and thus exhibit, for example, water and oil repellency
Data Source
AI summary
Diterminally amine-modified perfluoropolyether compounds of the general formula(wherein Rf is a perfluoropolyether group; each R1 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; R2, R3 and R4 are each independently substituted or unsubstituted monovalent hydrocarbon groups of 1 to 10 carbon atoms; each R5 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; each R6 is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group of 1 to 50 carbon atoms which may include at least one oxygen, nitrogen, sulfur or silicon atom; each occurrence of ‘m’ is independently 0, 1 or 2; and each occurrence of ‘n’ is independently an integer from 0 to 8) are provided. Such compounds have a good solubility in solvents and reactive resins.