Patent GB-1308794-A (GB)
Title: Polyfluoroisoalkoxyalkylamines and their salts
IPC: D06M13/322
Filed: 1970-10-13
Abstract: 1308794 Fluoroamines and hydrazines ALLIED CHEMICAL CORP 13 Oct 1970 [22 Oct 1969] 48667/70 Heading C2C [Also in Divisions C3 and D1] Compounds of general formula wherein (a) R f  is a group of general formula wherein (i) each of the groups R 5  to R 8 , which may be the same or different, is a fluorine or chlorine atom or a perhaloalkyl group having 1 to 10 carbon atoms, or two of the groups R 5  to R 8  together form a perhaloalkylene group having up to 20 carbon atoms, the halogen atoms of the perhaloalkyl and perhaloalkylene groups being fluorine or chlorine, each carbon atom in the groups R 5  to R 8  carrying at least one fluorine atom, not more than three of the groups R 5  to R 8  being perhaloalkyl groups, R 5  and R 6  not both being chlorine atoms, R 7  and R 8  not both being chlorine atoms, and R 5  to R 8  being preferably fluorine atoms or perfluoroalkyl groups having 1 to 3 carbon atoms; (ii) each of the groups X 1  and X 3 , which may be the same or different, is a hydrogen, fluorine, chlorine or bromine atom, and each of the groups X 2  and X 4 , which may be the same or different, is (1) a hydrogen, fluorine, chlorine or bromine atom, or (2) when X 1  and X 3  are hydrogen or fluorine atoms, a group of formula -CF 2 R 9  wherein R 9  is an alkyl or haloalkyl group having 1 to 8 carbon atoms, the halogen atom or atoms of the haloalkyl group being fluorine, chlorine or bromine; each of the groups and being the same or different, each of the groups -CX 1 X 2 -CX 3 X 4 - containing not more than two chlorine atoms or not more than one bromine atom, and X 1  to X 4  being preferably hydrogen, fluorine or chlorine atoms; (iii) r is 1 or 2; each of m and n, which may be the same or different, is 0 or an integer of 1 to 20, m + n being 0 to 20; and p is 0 or 1, n being at least 1 and X 3  and X 4  in the group being hydrogen atoms, when p is 0; (b) each of the groups R 1 , which may be the same or different, is a straight- or branched chain alkylene group having 1 to 6 carbon atoms; (c) R 2  is a straight- or branched-chain alkylene group having 1 to 20, preferably 1 to 6, carbon atoms; (d) Y is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; (e) each of the groups Y<SP>1</SP>, which may be the same or different, is a hydrogen atom; an alkyl or hydroxyalkyl group having 1 to 6 carbon atoms; an acyl group of formula R f CO- wherein R f  is as defined above; or a group of formula wherein R 1  and Y are as defined above, and B is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a group of formula R f CO- as defined above, Y<SP>1</SP> being preferably a hydrogen atom or an alkyl group; (f) W is (1) a substituted ammonium or #- substituted-hydrazinium group having up to 12 carbon atoms, the chemical bonds to the substituted nitrogen atom of the ammonium or hydrazinium group being all single bonds, and A is an anion; or W is (2) a substituted ammonium or hydrazinium group as defined above wherein a substituent carries a negative charge; or W is (3) a hydrazino group or an amino group of formula R 3 R 4 N- wherein each of the groups R 3  and R 4 , which are the same or different, is a hydrogen atom, an alkyl, hydroxyalkyl or cycloalkyl group having up to 6 carbon atoms or an aryl group having 6 to 9 carbon atoms, or R 3  and R 4  form together with the nitrogen atom a heterocyolic ring having up to 6 carbon atoms, subject to the proviso that only one of R 3  and R 4  is a cycloalkyl or aryl group, R 3  and R 4  being preferably hydrogen atoms or alkyl groups; and (g) each of a and c, which may be the same or different, is 0 or 1 and b is 0 or an integer of 1 to 20, b and c being 0 when a is 0; t is 0 or 1 and s is an integer of 1 to 3, t being 0 and s being 1 when W is (2) or (3), and t being 1 and s being an integer of 1 up to the negative charge of A when W is (1), are prepared by formation of the free base by (a) reduction of a nitrile or amide or (b) reaction of a fluoroalkoxyalkyl sulphonate with a polyamine or hydrazine, followed if desired by quaternization or other salification. The starting materials may be obtained by appropriate modification of the endgroups of telomers. The products have surfaceactive properties and may be used to impart oil-and-water repellency.