Aryl Monomers with Perfluorovinyl Ethers for Repellent Polymers
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Solution Overview
Problem
The existing production of water and oil repellents and soil resists relies on expensive linear perfluorinated alcohols, which are in short supply and require multi-step syntheses, necessitating the development of alternative starting materials.
Innovation Solution
Aryl compounds with partially fluorinated pendent groups and (meth)acrylate dependent groups are used for free radical polymerization, allowing the production of polymers suitable for water and oil repellents and soil resists without relying on linear uninterrupted perfluorinated alcohols, achieved through specific chemical reactions involving functionalized aryl rings and perfluorovinyl ethers.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If linear perfluorinated alcohols are used as starting materials, then water and oil repellents and soil resists can be produced, but the production cost increases and material availability decreases due to expensive raw materials and multi-step synthesis requirements
Solution Approach 1:
The patent segments the perfluorinated chain from the aromatic core by using perfluorovinyl ethers as separate building blocks that can be coupled to aromatic compounds. This allows independent optimization of the fluorinated portion (using readily available perfluorovinyl ethers) from the aromatic portion, simplifying manufacturing and improving material availability while maintaining the desired water and oil repellent properties.
Solution Approach 2:
The patent introduces perfluorovinyl ethers as intermediary compounds that serve as building blocks for constructing the final fluorinated aromatic products. These intermediaries are commercially available and easier to obtain than linear perfluorinated alcohols, thereby improving raw material availability while enabling the synthesis of target compounds with desired repellent properties.
2Ease of manufacture
If linear perfluorinated alcohols are used as starting materials, then water and oil repellents can be produced, but the manufacturing cost increases due to expensive raw materials and multi-step synthesis
Solution Approach 1:
The patent divides the synthesis into modular steps using perfluorovinyl ethers as pre-prepared building blocks. This segmentation reduces the number of synthesis steps required compared to starting from linear perfluorinated alcohols, thereby reducing both manufacturing cost and process complexity while maintaining product performance.
Solution Approach 2:
The patent utilizes perfluorovinyl ethers that have been pre-synthesized and are commercially available, eliminating the need to perform complex perfluorination steps in-house. This preliminary preparation of key building blocks reduces both the number of synthesis steps and the associated manufacturing costs.
3Quantity of substance
If alternative starting materials are used, then raw material availability improves, but the polymerization efficiency and product performance may be affected
Solution Approach 1:
The patent modifies the chemical parameters of the starting materials by using perfluorovinyl ethers with specific structural characteristics (perfluorinated vinyl group) that are compatible with free radical polymerization. The perfluorovinyl group provides appropriate reactivity and polymerization behavior, ensuring reliable polymerization efficiency while using more readily available raw materials.
Solution Approach 2:
The patent creates composite molecular structures by coupling perfluorovinyl ether units with aromatic compounds containing hydroxyl or carboxyl groups. This composite approach combines the desirable properties of perfluorinated chains (for repellency) with aromatic cores (for structural integrity and reactivity), achieving both improved material availability and maintained polymerization efficiency.
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
These aryl compounds serve as effective starting monomers for polyacrylate copolymers, providing water and oil repellency and stain resistance to fibrous substrates, offering a cost-effective and efficient alternative to traditional methods.
Implementation Method 1
Aryl compounds with partially fluorinated pendent groups and (meth)acrylate dependent groups are used for free radical polymerization
Data Source
AI summary
A compound of formula (I)whereinRf is —CF3, —C2F5, —CF2CFXCF3;X to —F, or —OC3F7;Y is —H, —Cl, or —Br;R is —O—C(O)—R1, —(CH2)nO—C(O)—R1, —(OCH2CH2)mOC(O)—R1; —(CH2)n(OCH2CH2)mO—R1;n is 1 to 10;m is 1 to 10;R1 is —C(R3)═CH2;R3 is H or CH3;a is 1 to 5; andb is 1 to 5.