Surfactant composition from polyfluoroalkylsulfonamido alkyl amines

1. A mixture of aminosulfonate or aminocarboxylate compositions, or mixtures thereof, which comprises:

i) at least one compound represented by

and

ii) at least one compound represented by

wherein:

a and b are independently chosen from integers such that a≧0, b>0, and a+b=3;

c and d are independently chosen from integers such that c≧0, d>0, and c+d=2;

each R f is the same in i) and ii) and chosen from a C 2 -C 12 polyfluoroalkyl, comprising partially or completely fluorinated linear or branched alkyl, 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;

each R 7 is independently chosen from a hydroxycarbonyl substituted C 1 to C 6 alkyl, and oxysulfonylalkyl,

their corresponding metal and ammonium salts, and mixtures thereof.

2. A surfactant comprising the mixture of aminosulfonate or aminocarboxylate compositions, or mixtures thereof, of claim 1 .

3. The mixture of claim 1 in the form of an aqueous film forming foam.

4. The mixture of claim 1 in the form of a fire fighting agent, wherein the fire fighting agent includes an aqueous film forming foam.

5. The mixture of claim 3 or claim 4 further comprising water or solvent or one or more surfactants.

6. A method of making a mixture of aminosulfonate or aminocarboxylate compositions, or mixtures thereof, of claim 1 comprising subjecting a mixture of amines including a polyfluoroalkylsulfonamido alkyl amine (Formula A) and a di(polyfluoroalkylsulfonamido alkyl) amine analog (Formula B) to N-alkylation with an N-alkylation reagent under suitable conditions to form the mixture of aminosulfonates or aminocarboxylates, or mixtures thereof, wherein the amines are represented by:

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 A); 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 B);

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; and

the N-alkylating reagent is selected from 1,3-propane sultone or 1,4-butane sultone or the N-alkylating reagent is a haloalkyl substituted reagent selected from the group consisting of ClCH 2 CH(OH)CH 2 SO 3 Na-hydrate, Cl(CH 2 ) 3 SO 3 Na and sodium monochloroacetate.

7. The method of claim 6 , wherein the N-alkylation reaction occurs in the presence of a base selected from sodium hydroxide or potassium hydroxide.

8. The method of claim 7 , further comprising an iodide salt selected from sodium iodide, potassium iodide or tetraalkyl ammonium iodide.

9. The method of claim 6 , wherein the mixture of amines is prepared by subjecting a polyfluoroalkylsulfonamido alkyl halide to amino-dehalogenation with ammonia or an amine under suitable conditions to form a mixture of at least a polyfluoroalkylsulfonamido alkyl amine and at least a 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 Cl, Br, I and mixtures thereof; and

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

10. The method of claim 9 , wherein the polyfluoroalkylsulfonamido alkyl halide (Formula 1) is prepared by reacting a polyfluoroalkylsulfonic compound with a monoamino alkyl halide, or salt thereof under suitable conditions to make a polyfluoroalkylsulfonamido alkyl halide wherein:

i) the polyfluoroalkylsulfonic compound is represented by

R f —(CH 2 ) n —S(O) 2 —Y  (Formula 3)

wherein Y is chosen from aryloxy, substituted aryloxy, or a halide; and

ii) the monoamino alkyl halide or salt thereof is represented by

HN(R 1 )—C(R 5 )(R 6 )—C m H 2m —X  (Formula 4A) or

[H 2 N(R 1 )—C(R 5 )(R 6 )—C m H 2m —X] + X −   (Formula 4B)

wherein each X is a halogen independently selected from CI, Br, and I.

11. The method of claim 9 , wherein the polyfluoroalkylsulfonamido alkyl halide (Formula 1) is prepared by reacting a polyfluoroalkylsulfonamido alkyl alcohol with a halogenating agent under suitable conditions to make a polyfluoroalkylsulfonamido alkyl halide wherein the polyfluoroalkylsulfonamido alkyl alcohol is represented by

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

12. The method of claim 11 , wherein the halogenating agent is selected from HCl, HBr, HI, SOCl 2 , SOBr 2 , SOI 2 , PCl 3 , PBr 3 , or PI 3 .

13. The method of claim 11 , wherein the polyfluoroalkylsulfonamido alkyl alcohol (Formula 5) is prepared by reacting a polyfluoroalkylsulfonic compound with an amino alkyl alcohol under suitable conditions to make the polyfluoroalkylsulfonamido compound wherein:

i) the polyfluoroalkylsulfonic compound is represented by

R f —(CH 2 ) n —S(O) 2 —Y  (Formula 3)

Y is chosen from aryloxy, substituted aryloxy, or a halide selected from F, Cl, or Br; and

ii) the amino alkyl alcohol is represented by

HN(R 1 )—C(R 5 )(R 6 )—C m H 2m —OH  (Formula 6).

14. A method of extinguishing a fire comprising contacting the fire with a composition containing the mixture of claim 1 .