1813-83-8Relevant articles and documents
Crosslinking of fluoroelastomers by "click" azide-nitrile cycloaddition
Tillet, Guillaume,Lopez, Gérald,Hung, Ming-Hong,Améduri, Bruno
, p. 1171 - 1173 (2015)
A fluoroelastomer that bears pendant nitrile groups is crosslinked with a telechelic bis-azido fluorinated curing agent by "click" azide-nitrile cycloaddition. Thermogravimetric analyses of the resulting press cured films reveal an improvement by 20 C of the thermal degradation profile under air, compared to that of the corresponding uncured fluoroelastomer.
Synthesis and preliminary assessments of ethyl-terminated perfluoroalkyl nonionic surfactants derived from tris(hydroxymethyl)acrylamidomethane
Barthelemy, Philippe,Ameduri, Bruno,Chabaud, Elodie,Popot, Jean-Luc,Pucci, Bernard
, p. 1689 - 1692 (1999)
(formula presented) We describe the synthesis and preliminary physicochemical and biological assessments of a new class of nonionic hybrid hydrofluoro amphiphiles derived from tris(hydroxymethyl)aminomethane (THAM). The synthesis of the hydrophobic tail of these amphiphiles is based on the preparation of an asymmetrical hydrofluorocarbon derivative containing an ethyl segment, a fluorocarbon core, and an ethyl thiol moiety. This molecule led to either THAM galactosylated monoadducts or telomers. These amphiphiles exhibit neither detergency toward cell membranes nor membrane protein denaturation.
SYNTHESIS OF FLUORINE-CONTAINING NITRO COMPOUNDS
Malik, A. A.,Archibald, T. G.,Tzeng, L. C.,Garver, L. C.,Baum, K.
, p. 291 - 300 (1989)
Fluoronitro alkanes (5a and 5b), possesing the structure -CF2CH2CH(NO2)2, were synthesized from 1-iodo-1H,1H,2H,2H-perfluoroalkanes by displacing the iodide with sodium nitrite and then oxidatively nitrating the 1-nitro-1H,1H,2H,2H-perfluoroalkanes with tetranitromathane.Reaction with formaldehyde gave the dinitroalcohols, 6a and 6b. α,ο-diiodoperfluoroalkames (1c and 1d) were similarly converted to tetranitrofluoroalkanes (5c and 5d), characterized as tetranitrodiols 6c and 6d, and Michael adducts with methyl acrylate, 7c and 7d.
Original fluorinated copolymers achieved by both azide/alkyne 'Click' reaction and hay coupling from tetrafluoroethylene telomers
Soules, Aurelien,Ameduri, Bruno,Boutevin, Bernard,Calleja, Gerard
experimental part, p. 4489 - 4499 (2011/10/12)
The synthesis and characterization of an original class of linear poly(alkyl aryl) ethers containing 1,2,3-triazolyl and fluorinated moieties based on oligo(tetrafluoroethylene) telomer are presented. These polymers were prepared, from α,ω-dipropargyl eth
Glucose-based surfactants with hydrogenated, fluorinated, or hemifluorinated tails: Synthesis and comparative physical-chemical characterization
Abla, Maher,Durand, Gregory,Pucci, Bernard
scheme or table, p. 8142 - 8153 (2009/04/04)
(Chemical Equation Presented) (Hemi)fluorinated hydrophobic chains have been found to minimize the denaturating propensity of surfactants toward membrane proteins. The work reported herein deals with the synthesis of a new series of non-ionic glucose-based surfactants endowed with a hybrid hemifluorocarbon chain. The convergent synthesis is based on a one-pot reduction/alkylation of hemifluorinated thioacetate and glucosylated trishydroxymethyl acrylamidomethane using NaBH4 in methanol. This "mild" alkylation was studied in order to improve yields and to pass up the use of an excess of commercially unavailable hemifluorinated thiols. The physical-chemical properties in aqueous solution of this novel series were studied by surface tension measurement and dynamic light scattering (DLS), as well as their behavior upon reverse-phase chromatography, and were compared with those of their hydrogenated and perfluorinated analogues. The atypical effect of the additional ethyl tip to the fluorinated chain was demonstrated by higher critical micellar concentration values and abnormal hydrophobicities measured by reverse-phase chromatography. Moreover, according to Israelachvili's concept, DLS studies showed that surfactants bearing bulkier polar head self-assemble into small and well-defined aggregates, suggesting the formation of spherical micelles rather than the cylindrical ones usually observed with classical fluorinated surfactants.
Synthesis of telechelic dienes from fluorinated α,ω-diiodoalkanes. Part I. Divinyl and diallyl derivatives from model I(C2F4)nI compounds
Manseri, A.,Ameduri, B.,Boutevin, B.,Kotora, M.,Hajek, M.,Caporiccio, G.
, p. 151 - 158 (2007/10/02)
The synthesis of five fluorinated non-conjugated dienes from commercially available α,ω-diiodoperfluoroalkanes is described.Preparation of the fluorinated divinyl derivatives H2C=CH(CF2)nCH=CH2 (n = 2, 4, 6) (2,2, 2,4 and 2,6) was effected by ethylenation of these diiodinated compounds in various ways followed by dehydroiodination in ethanolic potassium hydroxide.Allyl diolefines, H2C=CHCH2(CF2)nCH2CH=CH2 (4,4 and 4,6) were produced by the α,ω-bis-telomerization of allyl acetate followed by deiodoacetoxylation in the presence of zinc.The diacetate precursors 3,4 and 3,6 of the respective diallyls 4,4 and 4,6 were obtained rather than diacetate 3,2 because of the eventual decomposition of α,ω-diiodoperfluoroethane by β-scission.These five fluorinated non-conjugated dienes have been characterized by 1H, 13C and 19F NMR spectroscopy. - Keywords:Telechelic dienes; Fluorinated vinyl dienes; Fluorinated allyl dienes; α,ω-Diiodoperfluoroalkanes; NMR spectroscopy
Fluorine-containing α,β-bifunctional compounds and process for their production
-
, (2008/06/13)
A fluorine-containing α,ω-bifunctional compound having the formula: STR1 wherein each of R1 and R2 independently is a hydrogen atom, an alkyl group or an aralkyl group; X is --COOH, --COOR3, --COY or --NCO, wherein R3 is an alkyl group or an aralkyl group and Y is a halogen atom or N3 ; and n is an integer of at least 1 provided that when X is --COOH, n is an integer of at least 4.
SYNTHESIS OF FLUORINATED DIFUNCTIONAL MONOMERS
Takakura, T.,Yamabe, M.,Kato, M.
, p. 173 - 184 (2007/10/02)
In order to obtain fluorinated difunctional monomers for fluoropolyurethanes, we synthesized novel fluorinated aliphatic diisocyanates (OCNCH2(CF2)nCH2NCO) from corresponding diols (HOCH2CH2(CF2)nCH2CH2OH).Oxidation of the diols with chromium trioxide-sulfuric acid gave α,α,ω,ω-tetrahydroperfluoroalkylene dicarboxylic acids in high yields.Then treating the acids with phosphorus pentachloride afforded corresponding dicarboxyl chlorides, which are easily converted to dicarboxyl azides with hydrazoic acid-pyridine complex.Finally, on Curtius rearrangement of the azides, the end products, α,α,ω,ω-tetrahydroperfluoroalkylene diisocyanates were obtained in 53percent (n=4) and 19percent (n=6) yields from the starting diols.
Synthesis of Fluorinated Acetylenes
Baum, Kurt,Bedford, Clifford D.,Hunadi, Ronald J.
, p. 2251 - 2257 (2007/10/02)
New routes to fluorinated acetylenes were developed on the basis of additions of iodofluorocarbons to silylacetylenes.Free radical addition of α,ω-diiodoperfluoroalkanes to (trimethylsilyl)acetylene gave the iodotrimethylsilyl olefins Me3SiIC=CH(CF2)nCH=CISiMe3, which reacted with potassium tert-butoxide or DBU to give the (trimethylsilyl)acetylenes and, with an excess of the base, the free diacetylenes.Perfluoroalkyl iodides similarly gave (perfluoroalkyl)acetylenes.The addition of perfluoroheptyl iodide to phenylacetylene, followed by treatment with potassium tert-butoxide gave 1-phenylperfluorononyne.The peroxide-catalyzed reactionof perfluoroalkyl iodides and bis(trimethylsilyl)acetylene gave 1:1 adducts, RF(Me2SiCH2I)C=CHSiMe3, resulting from intramolecular hydrogen abstraction by the initially formed vinyl radical.However, the thermal reaction of perfluoroalkyl iodides and diiodides with bis(trimethylsilyl)acetylene in the presence of free iodine gave the (trimethylsilyl)acetylenes, which were desilylated with potassium fluoride.A route to diacetylenes was investigated on the basis of addition of perfluoroiodo compounds to ethylene, dehydroiodination, brominations, and eliminations.
