Fluorocarbon substituted triazines and condensates thereof

摘要

Water- and oil-resistant resinous compounds are prepared by heating together formaldehyde and a compound of formula: where X and Y are amino or hydrazino radicals, Rf is a perfluorinated alkyl radical of 4-12 carbon atoms, and Z is a group of formula: or where n is 1-12, m is 0-12, q is 1-13, and R is hydrogen or an alkyl radical of 1-6 carbon atoms. The resinous products are thermosetting, and can be cast in thin sheets or films, or can be used as coatings, e.g. on fibrous materials such as paper and textiles. It is stated that in place of formaldehyde, there may be used paraformaldehyde, hexamethylene tetramine, acetaldehyde or furfural. The monomeric triazine derivatives may also be employed as curing agents for epoxy-resins, such as bisphenol A-epichlorhydrin resins (Examples 3, 4 and 11). The above monomeric triazine derivatives, or their formaldehyde condensation products, may be used as hardening agents for alkyl-ureaformaldehyde and melamine-formaldehyde resins.ALSO:The invention comprises compounds of the formula: where X and Y are amino or hydrazino radicals, Rf is a perfluoroalkyl radical containing 4-12 carbon atoms, and Z is -SO2NH(CH2)n NH-, -SO2NR-, -CONH(CH2)mNH-, -CONH-, -(CH2)qO- or -(CH2)qNH-, where n is 1-12, m is 0-12, q is 1-13 and R is hydrogen or C1-6 alkyl. These compounds are prepared by normal condensation processes between suitable fluorinated compounds and mono-halogenated triazine derivatives, or between halogen derivatives of the fluorinated compound and a suitable triazine derivative. Thus 6-chloro-2,4-diaminotriazine may be condensed with RfCONHNH2 (obtained from RfCOF and hydrazine), or perfluoroalkyl-alkanols or alkylamines; or with alkylene diamines, to form 2,4-diamino-6-aminoalkylamino triazines, which are condensed with RfSO2Cl or perfluoroinated carboxylic acid esters or halides; RfSO2NHR can be condensed with cyanuric chloride, and the product with ammonia or hydrazine. Compounds containing the (CH2)q radical can be prepared by reacting RfSO2Cl or RfI with a distally unsaturated alkenol, or alkenoic acid or ester, followed by reductive dehydrohalogenation and, if necessary, saponification; the acids obtained can be converted into the amides (via the chlorides), which are reduced to amines; or the esters can be reduced to alcohols; these alcohols and amines are then used in condensation reactions with halogenated triazines. N-Propyl-perfluoro octane sulphonamide is pared by reacting C3H7NH2 with C8F17CO2F, and is converted into its sodio derivative by reaction with CH3ONa in methanol.