Patent GB-1015630-A (GB)
Title: New 1-fluoroacyl aziridines and their preparation and use
IPC: C08G73/02
Filed: 1964-10-21
Abstract: The invention comprises polymers of compounds of the formula <FORM:1015630/C3/1> in which A is CF3(CF2)m(CH2)n- or <FORM:1015630/C3/2> where m and n are 0-18 and p is 1-10 (see Division C2), and their production by heating the monomer, e.g. in the presence of a polymerization catalyst such as an alkali metal fluoride or cyanide, or an organic base such as pyridine, morpholine, triethylamine or ethyleneimine. Polymers may also be prepared from mixtures of the above monomers, or from mixtures of these with non-fluorinated aziridines, such as 1-butyryl-aziridine, glutaryl bis-ethylene-imide, 2,4,6, - tris (1 - aziridinyl) - s - triazine, and tris-(1-aziridinyl)-phosphine oxide. Solutions of the polymers are referred to, and the polymers may be used to fabricate objects such as gaskets, buttons, buckles and functional and ornamental objects, and in conventional coatings.ALSO:The invention comprises compounds of the formula <FORM:1015630/C2/1> where A is CF3(CF2)m(CH2)n-or <FORM:1015630/C2/2> in which m and n are 0-18 and p is 1-10; and their production by reacting ethylene imine with A1COX, in which X is halogen and A1 is CF3(CF2)m(CH2)n- or X-CO(CF2)p-, e.g. in the presence of an inert solvent and an acid-binding agent.  Examples prepare 1-perfluorooctanoyl-aziridine, 1-perfluorobutyryl-aziridin - perfluoroglutaryl bis - ethyleneimide and 1 - (12,12,13,13,14,14,15,15,16,16,17,17,18,18,18 pentadecafluoro - octadecanoyl) - aziridine (the acid CF3(CF2)6(CH2)10COOH being obtained by free-radical addition of CF3(CF2)6I to 10-undecenoic acid and reduction of I to H).  The above monomers are of use as chemical intermediates, e.g. for the reactions <FORM:1015630/C2/3> and <FORM:1015630/C2/4> The monomers may be polymerized (see Division C3) and the monomers and polmyers are used for treating textiles (see Division D1).ALSO:Fibrous materials of improved resistance to water, oil and dirt are obtained by treating them with a compound of formula <FORM:1015630/D1-D2/1> in which A is CF3(CF2)m(CH2)n-or <FORM:1015630/D1-D2/2> where m and n are 0-18 and p is 1-10 (see Division C2) or with a polymer thereof (see Division C3).  A monomer may be applied to the material in a volatile solvent such as benzone, toluene or benzotrifluoride and the solvent removed; the monomer is then cured, e.g. by standing at room temperature or by heating; polymerization catalysts, such as alkali metal fluorides or cyanides or organic bases, may be present in the monomer solution or may be applied to the material after the monomer solution.  The solvent may be one which swells the fibres of the material, e.g. dimethylformamide, dimethylsulphoxide, dimethylacetamide, N-acetylmorpholine, N-formylpiperidine, methylpyrrolidone and butyrolactone.  Or the monomer may be applied as an aqueous emulsion. The liquid used for treating the material may also contain known aziridines, e.g. glutaryl bis-(ethylene imide), 2, 4, 6-tris-(1-aziridinyl)-s-triazine or tris-(1-aziridinyl)-phosphine oxide.  Polymers of the above monomers may be applied to the material in a solvent which is later removed.  Specified materials are cotton, linen, hemp, jute, ramie, sisal, cellulose acetate rayons, cellulose acetate butyrate rayons, saponified acetate rayons, viscose rayon, cuprammonium rayon, ethyl cellulose, fibres prepared from starch, alginates, or pectins, wool, silk, animal hair, mohair, leather, fur, regenerated protein fibres derived from casein, soybean protein, peanut protein, zein, gluten, egg albumin, collagen, or keratin, nylon, polyurethane fibres, polyester fibres such as polyethylene terephthalate, polyacrylonitrile-based fibres, or inorganic fibres such as asbestos or glass.