- FLUORINATED URETHANE COMPOUNDS AND COMPOSITIONS CONTAINING THE SAME
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A fluorine-containing urethane compound of the general formula:[Rf-A1-(X1(OH))-(Y1)a-OC(=O)NH-]m I[-NHC(=O)O-Y2]n[-NHC(=O)O- ((ClCH2-)X2O)b-R1]k wherein I is a group remaining after an isocyanate group is removed from a polyisocyanate compound, Rf is a perfluoroalkyl group having 2 to 21 carbon atoms, A1 is a direct bond or a divalent organic group having 1 to 21 carbon atoms, X1 and X2 are trivalent linear or branched aliphatic group having 2 to 5 carbon atoms, Y1 is a divalent organic group having 0 to 5 carbon atoms and 0 to 2 nitrogen atoms (provided that at least one carbon atom or nitrogen atom is present) and at least one hydrogen atom, Y2 is a monovalent organic group optionally having a hydroxyl group, and R1 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, can impart high water- and oil-repellency.
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Page/Page column 7-8
(2008/06/13)
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- Synthesis of F-alkyl α-hydroxy acids and esters from F-alkyl epoxides and F-alkyl α-bromo acids and esters from F-alkyl bromohydrins
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F-alkyl α-hydroxy acids and F-alkyl α-bromo acids were prepared respectively by the nitric acid ring-opening oxidative reaction of F-alkyl oxiranes, and oxidation by chromic acid of F-alkyl bromohydrins. The synthesized acids were converted to the corresponding methyl esters which may prove to be useful in the synthesis of F-alkylated heterocycles.
- Ould Amanetoullah,Chaabouni,Baklouti
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p. 149 - 153
(2007/10/03)
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- Chemistry of [(perfluoroalkyl)methyl] oxiranes. Regioselectivity of ring opening with O-nucleophiles and the preparation of amphiphilic monomers
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The reactions of oxiranes RFCH2CH(-O-)CH2 (RF≡C4F9, C6F13, C8F17; 4a-4c) with a series of alkanols in the presence of a Lewis acid took place at the terminal carbon atom with complete regioselectivity. 2-Hydroxyethyl methacrylate and acrylate reacted similarly. The reaction with alkane diols was controlled to proceed with one or two molecules of the oxiranes chemoselectively. Non-regioselective, base-catalysed ring opening by methacrylic acid (83% terminal attack) was discussed on the basis of the hard and soft acids and bases (HSAB) concept. A convenient transformation of the oxiranes to the corresponding diols 13a-13c via dioxolane intermediates, and their conversion to bis-methacrylates, was accomplished with overall yields of 75%-79%. Thiourea converted the oxiranes into the corresponding thiiranes (15a-15c). The reactions afforded products generally in yields of 82%-98%.
- Cirkva, Vladimir,Ameduri, Bruno,Boutevin, Bernard,Paleta, Oldrich
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