Microbicidal Polymers And Methods Of Use Thereof

• US 20170000119A1
• Filed: 12/22/2014
• Published: 01/05/2017
• Est. Priority Date: 12/23/2013
• Status: Abandoned Application

• Current Assignee: Xmicrobial, LLC
• Original Assignee: Xmicrobial, LLC
• Inventors: Young, Shirley, Chiattello, Marion L., Nassar, Roger A., Oman, Mark
• Application Number:
  US15/106,597
• Publication Number:
  US 20170000119A1
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: A01N 25/02 containing liquids as carriers, diluents or solvents
• CPC Class Codes: A01N 25/08 containing solids as carriers or diluents
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A61L 12/145 Polymeric quaternary ammonium compounds
• CPC Class Codes: A61L 2/18 Liquid substances or solutions comprising solids or dissolved gases
• CPC Class Codes: A61L 2/22 Phase substances, e.g. smokes, aerosols or sprayed or atomised substances
• CPC Class Codes: A61L 2/232 layered or coated
• CPC Class Codes: C08G 2150/00 Compositions for coatings
• CPC Class Codes: C08G 2650/32 dendritic or similar
• CPC Class Codes: C08G 2650/50 containing nitrogen, e.g. polyetheramines or Jeffamines(r)
• CPC Class Codes: C08G 65/00 Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
• CPC Class Codes: C08G 65/332 containing carboxyl groups, or halides, or esters thereof
• CPC Class Codes: C08G 65/33303 containing amino group
• CPC Class Codes: C08G 65/337 containing other elements organic compounds containing halogens only as halides of a carboxyl group C08G65/332
• CPC Class Codes: C09D 171/02 Polyalkylene oxides
• CPC Class Codes: C09D 5/14 Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence

Abstract

Provided herewith are microbicidal polymers comprising an alkylene oxide backbone comprising one or more alkyl and/or alkylene oxide primary branches, in which at least one of the alkyl and/or alkylene oxide primary branches is functionalized with a quaternary ammonium or fluorinated group, or at least two of the alkyl and/or alkylene oxide primary branches are functionalized with a quaternary ammonium and fluorinated group, the primary branches optionally contain one or more alkyl and/or alkylene oxide secondary branches that are functionalized with a quaternary ammonium or fluorinated group, compositions comprising the polymer and a carrier, and methods of using the same.

Claims

1. A polymer comprising an alkylene oxide backbone to which are attached one or more alkyl or alkylene oxide primary branches, wherein at least one of the alkyl or alkyene oxide primary branches is functionalized with a quaternary ammonium group or a fluorinated group, or at least two of the alkyl or alkylene oxide primary branches are functionalized with a quaternary ammonium group and a fluorinated group, wherein the alkyl or alkylene oxide primary branches optionally contain one or more alkyl or alkylene oxide secondary branches that are functionalized with a quaternary ammonium group or a fluorinated group, wherein said polymer is associated with an anion to maintain electro-neutrality when a quaternary ammonium group is present.

2. The polymer of claim 1, wherein the alkylene oxide backbone comprises a propylene oxide backbone, an ethylene oxide backbone, or a backbone comprising both propylene oxide and ethylene oxide units.

3. The polymer of claim 1, wherein the primary branch comprises at least one ethylene oxide unit or at least one propylene oxide unit.

4. The polymer of claim 1, wherein the quaternary ammonium or fluorinated group is at a terminus of at least one of the alkyl or alkylene oxide primary branches.

5. The polymer of claim 1, wherein the alkylene oxide backbone is linked to at least 2 to 20 alkyl or alkylene oxide primary branches.

7. The polymer of claim 2, wherein the propylene oxide backbone has a formula:

8. The polymer of claim 1, wherein the alkyl or alkylene oxide primary branch, or the alkyl or alkylene oxide secondary branch, that is functionalized is of the formula

—

(CH₂)_n—

X,—

(CH₂CH₂O)_n—

X, or —

(CH₂CH₂CH₂O)_n—

X,

wherein

X is —

(CH₂)_m—

Y, when Y is a quaternary ammonium group or

X is —

(CH₂)_m—

NHC(O)—

Y, when Y is a fluorinated group,

m is 0 to 10, and

n is 1 to 2,500.

9. The polymer of claim 1, wherein at least one of the alkyl or alkylene oxide primary branches is functionalized with a quaternary ammonium group.

10. The polymer of claim 1, wherein the quaternary ammonium group has the formula —

N⁺R¹R²R³, wherein R¹, R², and R³ are independently selected from alkyl, alkenyl, cycloalkyl, and aryl.

15. The polymer of claim 1, wherein at least one of the alkyl or alkylene oxide primary branches is functionalized with a fluorinated group.

20. The polymer of claim 1, wherein at least two of the alkyl and/or alkylene oxide primary branches are functionalized with a quaternary ammonium group and a fluorinated group.

21. The polymer of claim 1, which is selected from

22. A composition comprising:

(i) a polymer of claim 1; and

(ii) a carrier.

27. A method of coating a surface, disinfecting a surface, or protecting a surface against growth of a microorganism comprising applying to the surface the composition of claim 22.

36. The method of claim 27, further comprising removing the polymer from the surface by washing the surface with a second solvent.

42. A coated surface comprising a surface and a composition of claim 22 coated on the surface.

49. A method of adjusting the solvation of the composition of claim 22 comprising selecting an appropriate alkylene oxide and alkyl groups in the backbone and branches and their number of repeat units and density of branches, and selecting a quaternary ammonium group or groups and/or a fluorinated group or groups to provide a polymer that is soluble in water, organic solvent, or a mixture thereof.

50. A method of adjusting the hydrophobicity, hydrophilicity, and/or fluorophilicity of the composition of claim 22 comprising selecting an appropriate alkylene oxide and alkyl groups in the backbone and branches and their number of repeat units and density of branches, and selecting a quaternary ammonium group or groups and/or a fluorinated group or groups to provide a polymer that is hydrophobic, hydrophilic, and/or fluorophilic.

51. A method of adjusting the hydrophobicity, hydrophilicity, fluorophilicity, and/or microbicidal performance of the coated surface of claim 42 comprising selecting an appropriate concentration of polymer on the surface by varying the polymer concentration in the carrier and by varying the number and methods of polymer coating.

6. (canceled)

11-14. -14. (canceled)

16-19. -19. (canceled)

23-26. -26. (canceled)

28-35. -35. (canceled)

37-41. -41. (canceled)

43-48. -48. (canceled)