Mixture of polyfluoroalkylsulfonamido alkyl amines

1. A mixture of polyfluoroalkylsulfonamido alkyl amines comprising:

i) at least one polyfluoroalkylsulfonamido alkyl amine represented by

R f —(CH 2 ) n —S(O) 2 —N(R 1 )—C(R 5 )(R 6 )—C m H 2m —N(R 4 ) 2   (Formula 7); and

ii) at least one di(polyfluoroalkylsulfonamido alkyl) analog of i) as represented by

[R f —(CH 2 ) n —S(O) 2 —N(R 1 )—C(R 5 )(R 6 )—C m H 2m —] 2 N +k (R 4 ) k+1 [Q − ] k   (Formula 8);

wherein

Q is a monovalent anion;

k is 0 or 1;

each R f is the same in i) and ii) and chosen from a C 2 -C 12 polyfluoroalkyl optionally interrupted by one to four groups chosen from: —O—, —S—, —S(O)—, and —S(O) 2 —;

each n in i) and ii) is the same and chosen from an integer from 0 to 6;

each m in i) and ii) is the same and chosen from an integer from 0 to 10;

each R 1 , R 5 , R 6 is independently chosen from hydrogen, C 1 to C 6 hydroxyalkyl, C 1 to C 6 halogen substituted alkyl, or a C 1 to C 6 linear or branched alkyl; provided that each R 1 in i) and ii) are the same, each R 5 in i) and ii) are the same, and each R 6 in i) and ii) are the same;

each R 4 in i) and ii) are the same and chosen from hydrogen or a C 1 to C 6 alkyl, or a C 1 to C 6 hydroxyalkyl;

wherein the mole ratio of i) to ii) is from about 10:1 to about 99:1.

2. The mixture of polyfluoroalkylsulfonamido alkyl amines of claim 1 wherein each R f is the same and chosen from CF 3 (CF 2 ) 5 , or CF 3 (CF 2 ) 3 .

3. The mixture of polyfluoroalkylsulfonamido alkyl amines of claim 1 wherein each n is the same and is 2.

4. The mixture of polyfluoroalkylsulfonamido alkyl amines of claim 1 wherein each R 1 is the same and chosen from hydrogen or methyl or ethyl.

5. The mixture of polyfluoroalkylsulfonamido alkyl amines of claim 4 wherein R 4 is chosen from hydrogen or methyl or ethyl.

6. The mixture of polyfluoroalkylsulfonamido alkyl amines of claim 1 wherein each R f is the same and chosen from CF 3 (CF 2 ) 5 , or CF 3 (CF 2 ) 3 ;

each n is the same and is 2; each R 1 , R 4 , R 5 and R 6 is the same and is hydrogen; and

each m is the same and is 2.

7. A method of making the mixture of polyfluoroalkylsulfonamido alkyl amines of claim 1 comprising subjecting a polyfluoroalkylsulfonamido alkyl halide to amino-de-halogenation with ammonia or an amine under suitable conditions to form the mixture of polyfluoroalkylsulfonamido alkyl amine and di(polyfluoroalkylsulfonamido alkyl)amine wherein:

i) the polyfluoroalkylsulfonamido alkyl halide is represented by

R f —(CH 2 ) n —S(O) 2 —N(R 1 )—C(R 5 )(R 6 )—C m H 2m —X  (Formula 1);

X is a halogen selected from CI, Br, I, and mixtures thereof; and

ii) the ammonia or amine is represented by N(R 4 ) 2 H (Formula 2).

8. The method of claim 7 wherein X is chlorine.