IP Library Granted Patent US 8,119,115
Granted Patent B2
US 8,119,115 · App. 11/499,227 · Granted Feb 21, 2012

Antiviral method

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Quick Facts
Patent No.
US 8,119,115
App. No.
11/499,227
Granted
Feb 21, 2012
Kind
B2
Abstract

This invention provides a method of inactivating non-enveloped virus particles. The method includes the step of contacting the virus with a virucidally-enhanced alcoholic composition that includes an alcohol, and an enhancer selected from the group consisting of cationic oligomers and polymers, proton donors, chaotropic agents, and mixtures thereof.

Claims (63)

1. A method of inactivating non-enveloped virus particles, the method comprising:

contacting non-enveloped virus particles under conditions suitable to inactivate non-enveloped virus particle with a virucidally-enhanced alcoholic composition comprising:

a. at least 50 percent by weight of a C 1-6 alcohol, based upon the total weight of the alcoholic composition; and

b. an enhancer selected from the group consisting of at least 0.01 percent by weight, based upon the total weight of the alcoholic composition of at least one proton donor, from about 0.25 to about 20 percent by weight, based upon the total weight of the alcoholic composition of at least one chaotropic agent, and mixtures thereof, with the proviso that when the alcoholic composition comprises a proton donor, the composition further comprises a synergistic amount of a cationic oligomer or polymer; thereby

inactivating non-enveloped virus particles, wherein said method exhibits at least a 1 log reduction against said non-enveloped virus particles in 60 seconds or less, compared to contacting said particles with a composition containing the same amount of C1-6 alcohol without said enhancer for the same amount of time.

2. The method of claim 1 , wherein said method is operative to inactivate enveloped virus particles and wherein said method further comprises:

contacting the enveloped virus particles with said composition.

3. The method of claim 1 , wherein said method is operative to kill microbes including gram positive bacteria, gram negative bacteria, fungi and parasites, and wherein said method further comprises:

contacting microbes with said composition.

4. The method of claim 1 , wherein said composition comprises from 50 to about 98 percent by weight of a C 1-6 alcohol, from 0.01 to about 1 percent by weight of a proton donor, and from about 0.02 to about 20 percent by weight of a cationic oligomer or polymer, all based upon the total weight of the alcoholic composition.

5. The method of claim 4 , wherein said cationic oligomer or polymer is a cationic polysaccharide, cationic copolymer of saccharide and a synthetic cationic monomer, cationic polyalkylene imine, cationic ethoxy polyalkylene imine, cationic poly [N-[3-(dialkylammonio)alkyl] N′[3-(alkyleneoxyalkylene dialkylammonio) alkyl]urea dichloride], vinyl caprolactam/VP/dialkylaminoalkyl alkylate copolymer, polyquaternium polymer or mixtures thereof.

6. The method of claim 5 , wherein said cationic oligomer or polymer is polyquaternium-2, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-32, polyquaternium-37, polyquaternium-39, polyquaternium-42, polyquaternium-43, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-51, polyquaternium-53, polyquaternium-55, polyquaternium-57, polyquaternium-58, polyquaternium-59, polyquaternium-60, polyquaternium-63, polyquaternium-64, polyquaternium-65, polyquaternium-68, or mixtures thereof.

7. The method of claim 4 , wherein said cationic oligomer or polymer is characterized by a charge density of at least about 0.1 meq/g.

8. The method of claim 1 , wherein said composition comprises from about 60 to about 95 percent by weight of a C 1-6 alcohol, a cationic oligomer or polymer, and a proton donor.

9. The method of claim 8 , wherein said composition comprises from about 0.015 to about 1 percent by weight of a proton donor, based upon the total weight of the alcoholic composition.

10. The method of claim 8 , wherein said proton donor is hydrochloric acid, nitric acid, phosphoric acid, phosphonic acid, boric acid, sulfuric acid, adipic acid, benzene 1,3,5 tricarboxylic acid, chlorosuccinic acid, choline chloride, cis-aconitic acid, citramalic acid, citric acid, cyclobutane 1,1,3,3 tetracarboxylic acid, cyclohexane 1,2,4,5 tetracarboxylic acid, cyclopentane 1,2,3,4 tetracarboxylic acid, diglycolic acid, fumaric acid, glutamic acid, glutaric acid, glyoxylic acid, isocitric acid, ketomalonic acid, lactic acid, maleic acid, malic acid, malonic acid, nitrilotriacetic acid, oxalacetic acid, oxalic acid, phytic acid, p-toluenesulfonic acid, salicylic acid, succinic acid, tartaric acid, tartronic acid, tetrahydrofuran 2,3,4,5 tetracarboxylic acid, tricarballylic acid, versene acids, 3-hydroxyglutaric acid, 2-hydroxypropane 1,3 dicarboxylic acid, glyceric acid, furan 2,5 dicarboxylic acid, 3,4-dihydroxyfuran-2,5 dicarboxylic acid, 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylic acid, 2-oxo-glutaric acid, dl-glyceric acid, 2,5 furandicarboxylic acid, or mixtures thereof.

11. The method of claim 1 , wherein said composition comprises a C 1-6 alcohol, a cationic oligomer or polymer, and a chaotropic agent.

12. The method of claim 1 , wherein said composition comprises from about 0.25 to about 20 percent by weight chaotropic agent, based upon the total weight of the alcoholic composition.

13. The method of claim 1 , wherein said chaotropic agent comprises thiourea, guanidine HCl, guanidine thiocyanate, aminoguanidine HCl, aminoguanidine bicarbonate, guanidine carbonate, guanidine phosphate, or mixtures thereof.

14. The method of claim 1 , wherein said method exhibits at least a 2 log reduction against said non-enveloped virus particles in 60 seconds or less.

15. The method of claim 1 , wherein said method exhibits at least a 3 log reduction against said non-enveloped virus particles in 60 seconds or less.

16. The method of claim 1 , wherein said non-enveloped virus particles are selected from members of the families Picornaviridae, Reoviridae, Caliciviridae, Adenoviridae and Parvoviridae.

17. The method of claim 1 , wherein said non-enveloped virus particles are selected from adenovirus, feline calicivirus, norovirus, papillomavirus, poliovirus, rhinovirus, hepatitis A virus, parvovirus, and rotavirus.

18. A method of producing a topical virucidal effect on mammalian skin against non-enveloped virus particles by applying a virucidally-enhanced alcoholic composition said method comprising topically applying to mammalian skin a virucidally-enhanced composition comprising:

a. at least 50 percent by weight of a C 1-6 alcohol, based upon the total weight of the alcoholic composition; and

b. an enhancer selected from the group consisting of at least 0.01 percent by weight, based upon the total weight of the alcoholic composition of at least one proton donor, from about 0.25 to about 20 percent by weight, based upon the total weight of the alcoholic composition of at least one chaotropic agent, and mixtures thereof, with the proviso that when the alcoholic composition comprises a proton donor, the composition further comprises a synergistic amount of a cationic oligomer or polymer; thereby producing a virucidal effect against non-enveloped virus particles on said skin, wherein said method exhibits at least a 1 log reduction against said non-enveloped virus particles in 60 seconds or less.

19. The method of claim 18 , wherein said method further produces a topical virucidal effect against enveloped viruses.

20. The method of claim 18 , wherein said method further produces a topical virucidal effect against microbes including gram positive bacteria, gram negative bacteria, fungi, parasites.

21. The method of claim 18 , wherein said composition comprises at least about 60 percent by weight of a C 1-6 alcohol, based upon the total weight of the alcoholic composition.

22. The method of claim 18 , wherein said composition comprises from 50 to about 98 percent by weight of a C 1-6 alcohol, from 0.01 to about 1 percent by weight of a proton donor, and from about 0.02 to about 20 percent by weight of a cationic oligomer or polymer, all based upon the total weight of the alcoholic composition.

23. The method of claim 22 , wherein said cationic oligomer or polymer is a cationic polysaccharide, cationic copolymer of saccharide and a synthetic cationic monomer, cationic polyalkylene imine, cationic ethoxy polyalkylene imine, cationic poly [N- [3-(dialkylammonio)alkyl] N′ [3-(alkyleneoxyalkylene dialkylammonio)alkyl]urea dichloride], vinyl caprolactam/VP/dialkylaminoalkyl alkylate copolymer, polyquaternium polymer or mixtures thereof.

24. The method of claim 22 , wherein said cationic oligomer or polymer is polyquaternium-2, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-32, polyquaternium-37, polyquaternium-39, polyquaternium-42, polyquaternium-43, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-51, polyquaternium-53, polyquaternium-55, polyquaternium-57, polyquaternium-58, polyquaternium-59, polyquaternium-60, polyquaternium-63, polyquaternium-64, polyquaternium-65, polyquaternium-68, or mixtures thereof.

25. The method of claim 22 , wherein said cationic oligomer or polymer is characterized by a charge density of at least about 0.1 meq/g.

26. The method of claim 18 , wherein said composition comprises from about 60 to about 95 percent by weight of a C 1-6 alcohol, a cationic oligomer or polymer, and a proton donor.

27. The method of claim 26 , wherein said composition comprises from about 0.015 to about 1 percent by weight of a proton donor, based upon the total weight of the alcoholic composition.

28. The method of claim 18 , wherein said proton donor is hydrochloric acid, nitric acid, phosphoric acid, phosphonic acid, boric acid, sulfuric acid, adipic acid, benzene 1,3,5 tricarboxylic acid, chlorosuccinic acid, choline chloride, cis-aconitic acid, citramalic acid, citric acid, cyclobutane 1,1,3,3 tetracarboxylic acid, cyclohexane 1,2,4,5 tetracarboxylic acid, cyclopentane 1,2,3,4 tetracarboxylic acid, diglycolic acid, fumaric acid, glutamic acid, glutaric acid, glyoxylic acid, isocitric acid, ketomalonic acid, lactic acid, maleic acid, malic acid, malonic acid, nitrilotriacetic acid, oxalacetic acid, oxalic acid, phytic acid, p-toluenesulfonic acid, salicylic acid, succinic acid, tartaric acid, tartronic acid, tetrahydrofuran 2,3,4,5 tetracarboxylic acid, tricarballylic acid, versene acids, 3-hydroxyglutaric acid, 2-hydroxypropane 1,3 dicarboxylic acid, glyceric acid, furan 2,5 dicarboxylic acid, 3,4-dihydroxyfuran-2,5 dicarboxylic acid, 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylic acid, 2-oxo-glutaric acid, dl-glyceric acid, 2,5 furandicarboxylic acid, or mixtures thereof.

29. The method of claim 18 , wherein said composition comprises C 1-6 alcohol, a cationic oligomer or polymer, and a chaotropic agent.

30. The method of claim 29 , wherein said composition comprises from about 0.25 to about 20 percent by weight chaotropic agent, based upon the total weight of the alcoholic composition.

31. The method of claim 29 , wherein said chaotropic agent is thiourea, guanidine HCl, guanidine thiocyanate, aminoguanidine HCl, aminoguanidine bicarbonate, guanidine carbonate, guanidine phosphate, or mixtures thereof.

32. The method of claim 18 , wherein said method exhibits at least a 2 log reduction against said non-enveloped virus particles in 60 seconds or less.

33. The method of claim 18 , wherein said method exhibits at least a 3 log reduction against said non-enveloped virus particles in 60 seconds or less.

34. The method of claim 18 , wherein said non-enveloped virus particles are selected from members of the families Picornaviridae, Reoviridae, Caliciviridae, Adenoviridae and Parvoviridae.

35. The method of claim 18 , wherein said non-enveloped virus particles are selected from adenovirus, feline calicivirus, norovirus, papillomavirus, poliovirus, rhinovirus, hepatitis A virus, parvovirus, and rotavirus.

36. A method of enhancing the efficacy of a C 1-6 alcohol against non-enveloped virus particles in a topical application to a surface, the method comprising:

combining said C 1-6 alcohol with an efficacy-enhancing amount of an enhancer selected from the group consisting of proton donors, chaotropic agents, and mixtures thereof, to form an antiviral composition that comprises at least 50 percent by weight of said C 1-6 alcohol, based upon the total weight of the composition, with the proviso that where the antiviral composition comprises a proton donor, the composition further comprises a synergistic amount of a cationic oligomer or polymer, wherein said antiviral composition exhibits an increased efficacy against non-enveloped viruses when applied to a surface for 60 seconds or less, compared to a composition containing the same amount of C 1-6 alcohol without said enhancer that is applied to a surface for the same amount of time.

37. The method of claim 36 , wherein said method further produces a topical virucidal effect against enveloped viruses.

38. The method of claim 36 , wherein said method further produces a topical virucidal effect against microbes including gram positive bacteria, gram negative bacteria, fungi, parasites.

39. The method of claim 36 , wherein said composition comprises at least about 60 percent by weight of a C 1-6 alcohol, based upon the total weight of the antiviral composition.

40. The method of claim 36 , wherein said composition comprises from about 50 to about 98 percent by weight of a C 1-6 alcohol, from about 0.01 to about 1 percent by weight of a proton donor, and from about 0.02 to about 20 percent by weight of a cationic oligomer or polymer, all based upon the total weight of the alcoholic composition.

41. The method of claim 40 , wherein said cationic oligomer or polymer is a cationic polysaccharide, cationic copolymer of saccharide and a synthetic cationic monomer, cationic polyalkylene imine, cationic ethoxy polyalkylene imine, cationic poly [N-[3-(dialkylammonio)alkyl] N′[3-(alkyleneoxyalkylene dialkylammonio)alkyl]urea dichloride], vinyl caprolactam/VP/dialkylaminoalkyl alkylate copolymer, polyquaternium polymer or mixtures thereof.

42. The method of claim 40 , wherein said cationic oligomer or polymer includes polyquaternium-2, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-32, polyquaternium-37, polyquaternium-39, polyquaternium-42, polyquaternium-43, polyquaternium-44, polyquaternium-46, polyquaternium-47, polyquaternium-51, polyquaternium-53, polyquaternium-55, polyquaternium-57, polyquaternium-58, polyquaternium-59, polyquaternium-60, polyquaternium-63, polyquaternium-64, polyquaternium-65, polyquaternium-68, or mixtures thereof.

43. The method of claim 40 , wherein said cationic oligomer or polymer is characterized by a charge density of at least about 0.1 meq/g.

44. The method of claim 36 , wherein said composition comprises a C 1-6 alcohol, a cationic oligomer or polymer, and a proton donor.

45. The method of claim 44 , wherein said composition comprises from about 0.015 to about 1 percent by weight of a proton donor, based upon the total weight of the alcoholic composition.

46. The method of claim 44 , wherein said proton donor is hydrochloric acid, nitric acid, phosphoric acid, phosphonic acid, boric acid, sulfuric acid, adipic acid, benzene 1,3,5 tricarboxylic acid, chlorosuccinic acid, choline chloride, cis-aconitic acid, citramalic acid, citric acid, cyclobutane 1,1,3,3 tetracarboxylic acid, cyclohexane 1,2,4,5 tetracarboxylic acid, cyclopentane 1,2,3,4 tetracarboxylic acid, diglycolic acid, fumaric acid, glutamic acid, glutaric acid, glyoxylic acid, isocitric acid, ketomalonic acid, lactic acid, maleic acid, malic acid, malonic acid, nitrilotriacetic acid, oxalacetic acid, oxalic acid, phytic acid, p-toluenesulfonic acid, salicylic acid, succinic acid, tartaric acid, tartronic acid, tetrahydrofuran 2,3,4,5 tetracarboxylic acid, tricarballylic acid, versene acids, 3-hydroxyglutaric acid, 2-hydroxypropane 1,3 dicarboxylic acid, glyceric acid, furan 2,5 dicarboxylic acid, 3,4-dihydroxyfuran-2,5 dicarboxylic acid, 3,4-dihydroxytetrahydrofuran-2,5-dicarboxylic acid, 2-oxo-glutaric acid, dl-glyceric acid, 2,5 furandicarboxylic acid, or mixtures thereof.

47. The method of claim 36 , wherein said composition comprises C 1-6 alcohol, a cationic oligomer or polymer, and a chaotropic agent.

48. The method of claim 36 , wherein said composition comprises from about 0.25 to about 20 percent by weight chaotropic agent, based upon the total weight of the antiviral composition.

49. The method of claim 36 , wherein said chaotropic agent is urea, thiourea, guanidine HCl, guanidine thiocyanate, aminoguanidine HCl, aminoguanidine bicarbonate, guanidine carbonate, guanidine phosphate, or mixtures thereof.

50. The method of claim 36 , wherein said method exhibits at least a 1 log reduction against said non-enveloped virus particles in 60 seconds or less.

51. The method of claim 36 , wherein said method exhibits at least a 3 log reduction against said non-enveloped virus particles in 60 seconds or less.

52. The method of claim 36 , wherein said surface includes a porous or non-porous surface.

53. The method of claim 36 , wherein said non-enveloped virus particles are selected from members of the families Picornaviridae, Reoviridae, Caliciviridae, Adenoviridae and Parvoviridae.

54. The method of claim 36 , wherein said non-enveloped virus particles are selected from adenovirus, feline calicivirus, norovirus, papillomavirus, poliovirus, rhinovirus, hepatitis A virus, parvovirus, and rotavirus.

Assignments (8)
RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL, RECORDED ON OCTOBER 27, 2023 AT REEL 065382 FRAME 0587 Recorded Apr 22, 2026
From: SILVER POINT FINANCE, LLC, AS COLLATERAL AGENT
To: GOJO INDUSTRIES, INC.
Reel/Frame 075435/0852 →
RELEASE OF SECURITY INTEREST Recorded Apr 7, 2026
From: PNC BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: GOJO INDUSTRIES, INC.
Reel/Frame 074903/0480 →
SECURITY INTEREST Recorded Oct 27, 2023
From: GOJO INDUSTRIES, INC.
To: SILVER POINT FINANCE, LLC, AS COLLATERAL AGENT
Reel/Frame 065382/0587 →
SECURITY INTEREST Recorded Oct 26, 2023
From: GOJO INDUSTRIES, INC.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 065369/0253 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2012
From: STEEL CITY CAPITAL FUNDING, A DIVISION OF PNC BANK, NATIONAL ASSOCIATION
To: GOJO INDUSTRIES, INC.
Reel/Frame 028575/0804 →
SECURITY AGREEMENT Recorded Dec 15, 2010
From: GOJO INDUSTRIES, INC.
To: STEEL CITY CAPITAL FUNDING, A DIVISION OF PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 025495/0678 →
SECURITY AGREEMENT Recorded Dec 9, 2010
From: GOJO INDUSTRIES, INC.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 025454/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2006
From: SNYDER, MARCIA; MACINGA, DAVID R.; ARBOGAST, JAMES W.
To: GOJO INDUSTRIES, INC.
Reel/Frame 018165/0764 →