Fluorine and phosphorous-containing amphiphilic molecules with surfactant properties

Claim 1

A compound of the general formula: ##STR4## wherein: m is 0 or 1; R 1 represents: R F (CH 2 ) a --(CH═CH) b --(CH 2 ) c --(CH═CH) d --(CH 2 ) e --A--; R F --(CH 2 ) f --OCH 2 CH(CH 2 OH)CH 2 --A--; R F --(CH 2 ) g --OCH 2 CH(CH 2 OH)--A--; wherein --A-- represents --O--, --C(O)O--, --R 6 (R 7 )N + --, (wherein each of R 6 and R 7 represents C 1 -C 4 alkyl or hydroxyethyl), --(CH 2 ) n --, wherein n=0 or 1, or --C(O)N(R 9 )--(CH 2 ) q --B, wherein q is an integer from 0 to 12, B represents --O-- or --C(O)--, and R 9 is hydrogen or R 6 , and wherein the sum of a+c+e is from 0 to 11, the sum b+d is from 0 to 12 and each of f and g is from 1 to 12; R F --(CH 2 --CH 2 --O) h --; R F --(CH(CH 3 )CH 2 O) h --; or R F (--CH 2 --CH 2 --S) h --, wherein h is from 1 to 12; and wherein R F represents a fluorine -containing moiety having one of the following structures: (a) F(CF 2 ) i --, wherein i is from 2 to 12, (b) (CF 3 ) 2 CF(CF 3 ) j --, wherein j is from 0 to 8, (c) R F 1(CF 2 CF(CF 3 )) k --, wherein k is from 1 to 4 , and R F 1 represents CF 3 --, C 2 F 5 -- or (CF 3 ) 2 CF--, (d) R F 2 (R F 3)CFO (CF 2 CF 2 ) l --, wherein l is from 1 to 6 and wherein each of R F 2 and R F 3 independently represents CF 3 --, C 2 F 5 --, n--C 3 F 7 -- or CF 3 CF 2 CF(CF 3 )-- or R F 2 and R F 3 taken together represent --(CF 2 ) 4 -- or --(CF 2 ) 5 --, provided that in compounds of the general formula Ia, when m=0, R 1 is R F (CH 2 ) a --(CH═CH) b --(CH 2 ) c --(CH═CH) d --(CH 2 ) e --A--, wherein --A-- is --(CH 2 ) n -- and n=0, each of R F 2 and R F 3 represents CF 3 --, and l is 1, then the sum of b+d must be 1 or more; or (e) one of the structures (a) to (d) in which one or more of the fluorine atoms are replaced by one or more hydrogen or bromine atoms and/or at least two chlorine atoms in a proportion such that at least 50% of the atoms bonded to the carbon skeleton of R F are fluorine atoms, and wherein R F contains at least 4 fluorine atoms, R 2 represents R 1 , hydrogen or a group OR, wherein R represents a saturated or unsaturated C 1 -C 20 alkyl or C 4 -C 20 acyl; and when m is 1, R 1 and R 2 may exchange their positions; and each of X and Y independently represent: hydroxyl; --OCH 2 CH(OH) CH 2 OH; --O(CH 2 CH 2 O) n R 3 , wherein n is an integer from 1 to 5; and R 3 represents a hydrogen atom or C 1 -C 4 alkyl group; --NR 4 R 5 or N + R 4 R 5 R 8 , wherein each of R 4 , R 5 and R 8 independently represents a hydrogen atom; a C 1 -C 4 alkyl group; --CH 2 CH 2 O(CH 2 CH 2 O) s R 3 , wherein s represents an integer of from 1 to 5, or R 4 and R 5 when taken together represent --(CH 2 ) q wherein q is an integer of from 2 to 5, or when with the nitrogen atom R 4 and R 5 form a morpholino group; --O(CH 2 ) p Z wherein Z represents a 2-aminoacetic acid group, --NR 4 R 5 or --N + R 4 R 5 R 8 where R 8 is as defined for R 4 and R 5 above and p is an integer of from 1 to 5; with the proviso that X and Y do not both represent hydroxyl; further provided for compounds of the general formula Ia, that when m=0 or 1, R 2 is H, and R 1 is R F (CH 2 ) a --(CH═CH) b --(CH 2 ) c --(CH═CH) d --A--, in which A is CH 2 or O; or, when m=0 and R 1 is R F --CH 2 --CH 2 --O) h , one of X and Y is not CH 2 CH(OH)CH 2 OH when the other is OH or an ionized form derived from OH.