Polymeric aromatic N-halo sulfonamides

1. A polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal.

2. The polymer of claim 1 , wherein y is 1 and Q comprises an ester linkage.

3. The polymer of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen or alkyl from C 1 to C 12 ; X is chlorine, bromine, fluorine, or iodine; and M is sodium or potassium.

4. The polymer of claim 1 , having the following Formula (II):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen;

wherein M is an alkali or alkaline earth metal; and

wherein n is the degree of polymerization.

5. The polymer of claim 1 , wherein the monomer of Formula (I) has the following Formula (III):

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal.

6. The polymer of claim 1 , having the following Formula (IV):

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen;

wherein M is an alkali or alkaline earth metal; and

wherein n is the degree of polymerization.

7. The polymer of claim 1 , wherein the monomer of Formula (I) has the following Formula (V):

wherein X is chlorine, bromine, fluorine, or iodine; and

M is an alkali or alkaline earth metal.

8. The polymer of claim 1 , having the following Formula (VI):

wherein X is chlorine, bromine, fluorine, or iodine;

M is an alkali or alkaline earth metal; and

wherein n is the degree of polymerization.

9. The polymer of claim 1 , wherein the monomer of Formula (I) has the following Formula (VII):

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal.

10. The polymer of claim 1 , having the following Formula (VIII):

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen;

wherein M is an alkali or alkaline earth metal; and

wherein n is the degree of polymerization.

11. The polymer of claim 1 , wherein the monomer of Formula (I) has the following Formula (IX):

wherein X is chlorine, bromine, fluorine, or iodine; and

M is an alkali or alkaline earth metal.

12. The polymer of claim 1 , having the following Formula (X):

wherein X is chlorine, bromine, fluorine, or iodine;

M is an alkali or alkaline earth metal; and

wherein n is the degree of polymerization.

13. The polymer of claim 1 , further comprising a monomer of the following Formula (XI):

wherein B is a trivalent linkage;

wherein W is a divalent linkage and z is 0 or 1; and

wherein R 5 and R 6 are independently selected from linear or branched alkyl from C 1 to C 12 .

14. The polymer of claim 13 , wherein B is —CH 2 —CH—; z is 0; and R 5 and R 6 are methyl.

15. The polymer of claim 1 , comprising a monomer of Formula (V) and a monomer of Formula (XI):

wherein X is chlorine, bromine, fluorine, or iodine;

M is an alkali or alkaline earth metal;

wherein B is a trivalent linkage;

wherein W is a divalent linkage and z is 0 or 1; and

wherein R 5 and R 6 are independently selected from linear or branched alkyl from C 1 to C 12 .

16. The polymer of claim 15 , wherein X is chlorine and M is sodium or potassium.

17. The polymer of claim 1 , comprising a monomer of Formula (IX) and a monomer of Formula (XI):

wherein X is chlorine, bromine, fluorine, or iodine;

M is an alkali or alkaline earth metal;

wherein B is a trivalent linkage;

wherein W is a divalent linkage and z is 0 or 1; and

wherein R 5 and R 6 are independently selected from linear or branched alkyl from C 1 to C 12 .

18. The polymer of claim 17 , wherein X is chlorine and M is sodium or potassium.

19. A polymer having the following Formula (VI):

wherein X is chlorine; M is sodium or potassium; and n is the degree of polymerization.

20. A polymer having the following Formula (X):

wherein X is chlorine; M is sodium or potassium; and n is the degree of polymerization.

21. A process for making a polymer having the following Formula (VI):

wherein X is chlorine; M is sodium or potassium; and n is the degree of polymerization, the process comprising:

providing polystyrene;

sulfonating the polystyrene to produce polystyrene sulfonic acid;

chlorinating the sulfur atom to produce polystyrene sulfonyl chloride;

reacting the polystyrene sulfonyl chloride with ammonia to amidate the sulfur atom; and

halogenating the nitrogen atom with an alkali metal hypohalide to produce the polymer of Formula (VI).

22. A process for eliminating the odor in an substrate, comprising:

providing a liquid solution comprising (i) a solvent or an aqueous medium; and (ii) a polymer having an aromatic N-halo sulfonamide pendant group, the polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal; and

applying the liquid solution to the substrate.

23. The process of claim 22 , wherein A is —CH 2 —CH—; y is 0; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

24. The process of claim 22 , wherein A is —CH 2 —CH—; y is 1 and Q comprises an ester linkage; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

25. A process for killing bacteria or fungi contained on a substrate, comprising:

providing a liquid solution comprising (i) a solvent or an aqueous medium; and (ii) a polymer having an aromatic N-halo sulfonamide pendant group, the polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal; and

applying the liquid solution to the substrate.

26. The process of claim 25 , wherein A is —CH 2 —CH—; y is 0; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

27. The process of claim 25 , wherein A is —CH 2 —CH—; y is 1 and Q comprises an ester linkage; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

28. The process of claim 25 , wherein the liquid solution further comprises a wetting agent.

29. The process of claim 28 , wherein the concentration of the wetting agent is from about 0.1% to 5%.

30. The process of claim 25 , wherein the pH of the liquid solution is between 6 and 14.

31. A process for sanitizing the teats of a bovine, comprising:

providing a liquid solution comprising (i) a solvent or an aqueous medium; and (ii) a polymer having an aromatic N-halo sulfonamide pendant group, the polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal; and

applying the liquid solution to a teat of a bovine.

32. The process of claim 31 , wherein A is —CH 2 —CH—; y is 0; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

33. The process of claim 31 , wherein A is —CH 2 —CH—; y is 1 and Q comprises an ester linkage; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

34. A process for curing diseased fish of bacterial infections, comprising:

providing a liquid solution comprising (i) a solvent or an aqueous medium; and (ii) a polymer having an aromatic N-halo sulfonamide pendant group, the polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, ON, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal; and

allowing the diseased fish to swim in the liquid solution for an effective amount of time.

35. The process of claim 34 , wherein A is —CH 2 —CH—; y is 0; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

36. The process of claim 34 , wherein A is —CH 2 —CH—; y is 1 and Q comprises an ester linkage; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

37. A process for killing bacteria or fungi contained on a substrate, comprising:

providing a polymer having an aromatic N-halo sulfonamide pendant group, the polymer comprising a monomer of the following Formula (I):

wherein A is a trivalent linkage;

wherein Q is a divalent linkage and y is 0 or 1;

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, CF 3 , COOH, derivatized COOH, an ester or alkylated amide, COOM, CN, NO 2 , SO 3 H, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, and linear or branched alkyl from C 1 to C 12 , wherein the linear or branched alkyl moiety may be substituted at one or more of the aliphatic hydrogens;

wherein X is halogen; and

wherein M is an alkali or alkaline earth metal;

wetting the polymer with a liquid; and

rubbing the substrate with the polymer.

38. The process of claim 37 , wherein A is —CH 2 —CH—; y is 0; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.

39. The process of claim 37 , wherein A is —CH 2 —CH—; y is 1 and Q comprises an ester linkage; R 1 , R 2 , R 3 , and R 4 are hydrogen; X is chlorine; and M is sodium or potassium.