A number of polymers of acrylates of fluorine‐containing ether alcohols were prepared and studied. The side‐chain structures investigated are: CF3CH2OCH2CH2OCO, CF2HCF2OCH2CH2OCO, CF2HCF2(OCH2CH2)2OCO, CF3CF2CF2CH2OCH2CH2OCO,
and RfOCF2CF2CH2OCO, where Rf equals CF3, CF3CF2, CF3CF2CF2, and CF3CF2CF2CF2. Of these, the last group has glass transition and stiffening temperatures 20–25°C. lower than those of most of the others, together with the small swelling in solvents characteristic of the RfCH2OCO series. It is concluded that polymer behavior, particularly the modulus‐temperature and solubility characteristics, may be very profoundly affected by the nature of the side chains. An interpretation of the behavior of the polyacrylates of the fluorinated ether‐alcohols in terms of increased side‐chain flexibility due to ether “swivel joints” is attractive, but may not be justified.
The preparation and properties of the homopolymers and butadiene copolymers of the 1,1‐dihydroperfluoroalkyl acrylates, CF3(CF2)nCH2OCOCHCH2. where n has been varied from 0 to 8, are described. Up through the hexyl member, the homopolymers are rubbers which can be vulcanized and which show outstanding resistance to solvents, particularly hydrocarbons. The octyl member can be obtained in either crystalline or rubbery form. The effect of side‐chain length on glass transition temperature and solubility is discussed. Incorporation of butadiene increases flexibility at low temperatures, although at some sacrifice of solvent resistance.
The homopolymer and butadiene copolymers of 1,1‐dihydroperfluorobutyl acrylate form a new class of vulcanizable elastomers with interesting and useful properties, of which solvent resistance is the most outstanding. The homopolymer (poly‐FBA), vulcanized by means of a polyfunctional amine in the presence of a reinforcing pigment, appears most promising because it offers the following unusual combination of desirable properties: (1) resistance to hydrocarbon solvents; (2) resistance to a variety of lubricants, hydraulic fluids, and similar high boiling liquids at temperatures up to 400°F.; (3) resistance to oxidation by ozone and fuming nitric acid; (4) fair stability and physical properties in air at elevated temperatures. It was shown that many of these properties depend upon compounding recipes and that further improvements can be anticipated.
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