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US4654208A Expired / Lapsed US ⏱️ 0.0 years remaining

Anti-microbial compositions comprising an aqueous solution of a germicidal polymeric nitrogen compound and a potentiating oxidizing agent

Assignee: Individual
•
Filing: 1985-02-12
•
Granted: 1987-03-31
•
Expires: 2005-02-12
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Abstract

Abstract An anti-microbial composition comprises an aqueous solution of a germicidal polymeric nitrogen compound and an oxidizing agent which potentiates the activity of the compound. The polymeric nitrogen compound includes a germicidal quaternary ammonium compound or a polyguanide compound. The oxidizing agent has a standard reduction potential between 0.85 and 2.0 volts, is soluble in water, non-toxic and enhances the activity germicidal of the nitrogen polymer at low concentrations. Suitable oxidizing agents include halogen oxides, oxyhalogens, halogens, and inorganic and organic peroxides.

Inventors

  • 👤 Richard F. Stockel
  • 👤 Murray Jelling

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 08:05
CPC Classifications
A; A61; A61L; A61L12/00; A61L12/08; A61L12/14; A61L12/143; A61L12/145; A01; A01N; A01N59/00; A61L12/10; A61L12/102

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 283 words
An anti-microbial composition comprising an aqueous solution of: (1) 0.001 to 0.05 percent by weight of a germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene that is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR9## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6, or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary condensed amine with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 0.05 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 2
Dependent Claim 283 words
An anti-microbial composition comprising an aqueous solution of: (1) 0.001 to 0.05 percent by weight of a germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene that is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR9## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6, or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary condensed amine with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 0.05 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 3
Dependent Claim 22 words
An anti-microbial composition according to claim 1, wherein said oxidizing agent includes halogen oxides, oxyhalogens, halogens, inorganic and organic peroxides and permanganate.
Claim 4
Dependent Claim 33 words
An anti-microbial composition according to claim 2, wherein said inorganic and organic peroxides includes hydrogen peroxide, persulfates, peroxyacetic acid, perborates, percarbonates, lower alkylhydroperoxides and the peroxy acids or salts of molybdenum, or tungsten.
Claim 5
Dependent Claim 14 words
An anti-microbial composition according to claim 1, wherein said oxidizing agent is hydrogen peroxide.
Claim 6
Dependent Claim 18 words
An anti-microbial composition according to claim 1, wherein the pH of said composition is about 5.5 to 8.5.
Claim 7
Dependent Claim 18 words
An anti-microbial compositions according to claim 1, wherein the pH of said composition is about 6.5 to 7.5.
Claim 8
Dependent Claim 16 words
An anti-microbial composition according to claim 1 in which said polymeric compound is polymeric hexamethylene diguanide.
Claim 9
Dependent Claim 28 words
An anti-microbial composition according to claim 1, wherein said polymeric quaternary ammonium compound is made by condensing a difunctional tertiary amine with a molar equivalent quantity of 1,4-dichloro-2-butene.
Claim 10
Dependent Claim 36 words
An anti-microbial composition according to claim 1, wherein said polymeric quaternary ammonium compound is made by condensing a mixture of two or more difunctional tertiary amines and a molar equivalent equal to their sum of 1,4-dichloro-2-butene.
Claim 11
Dependent Claim 48 words
An anti-microbial composition according to claim 1, wherein said polymeric quaternary ammonium compound is made by condensing a mixture of a difunctional amine and a monofunctional tertiary amine, wherein the molar quantity of the difunctional amine is greater than the molar quantity of the monofunctional amine, with 1,4-dichloro-2-butene.
Claim 12
Dependent Claim 14 words
An anti-microbial composition according to claim 8, wherein said oxidizing agent is hydrogen peroxide.
Claim 13
Dependent Claim 15 words
An anti-microbial composition according to claim 8 wherein said oxidizing agent is stabilized chlorine dioxide.
Claim 14
Dependent Claim 14 words
An anti-microbial composition according to claim 9 wherein said oxidizing agent is hydrogen peroxide.
Claim 15
Dependent Claim 14 words
An anti-microbial composition according to claim 10 wherein said oxidizing agent is hydrogen peroxide.
Claim 16
Dependent Claim 15 words
An anti-microbial composition according to claim 10 wherein said oxidizing agent is stabilized chlorine dioxide.
Claim 17
Dependent Claim 15 words
An anti-microbial composition according to claim 1 wherein said oxidizing agent is stabilized chlorine dioxide.
Claim 18
Dependent Claim 17 words
An anti-microbial composition according to claim 1 wherein said anti-microbial polymeric quaternary ammonium compound is Onamer M.
Claim 19
Dependent Claim 14 words
An anti-microbial composition according to claim 17, wherein said oxidizing agent is hydrogen peroxide.
Claim 20
Dependent Claim 15 words
An anti-microbial composition according to claim 17 wherein said oxidizing agent is stabilized chlorine dioxide.
Claim 21
Independent Claim 308 words
A method of treating industrial materials such as the biocidal treatment of water and the sterilization of hospital rooms, which comprises contacting the same with an antimicrobial composition comprising an aqueous solution of: (1) 0.001 to 5 percent by weight of germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene that is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR10## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" are is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6 or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary amine condensed with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 5 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 22
Independent Claim 308 words
A method of treating industrial materials such as the biocidal treatment of water and the sterilization of hospital rooms, which comprises contacting the same with an antimicrobial composition comprising an aqueous solution of: (1) 0.001 to 5 percent by weight of germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene that is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR10## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" are is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6 or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary amine condensed with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 5 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 23
Dependent Claim 15 words
A method according to claim 20 in which the polymeric compound is polymeric hexamethylene diguanide.
Claim 24
Independent Claim 295 words
A method of treating soft contact lenses by contacting the same with an antimicrobial composition comprising an aqueous solution of: (1) 0.001 to 0.05 percent by weight of germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene than is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR11## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" are is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6 or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary amine condensed with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 0.05 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 25
Independent Claim 295 words
A method of treating soft contact lenses by contacting the same with an antimicrobial composition comprising an aqueous solution of: (1) 0.001 to 0.05 percent by weight of germicidal polymer selected from the group consisting of: (a) an anti-microbial polymeric quaternary ammonium compound made by condensing a difunctional tertiary amine, or a mixture of two or more difunctional tertiary amines, and a molar quantity of 1,4-dichloro-2-butene than is equal to the moles of said difunctional tertiary amine or the molar sum of the difunctional tertiary amines in the mixture, the difunctional tertiary amines being of the type ##STR11## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents, wherein R' and R" are either the same of different and wherein they be (i) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" are is no greater than 36, (ii) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (iii) benzyl, (iv) alkyl benzyl or (v) combined with N to form a heterocyclic group of either 5, 6 or 7 atoms; or said difunctional tertiary amines and a monofunctional tertiary amine condensed with 1,4-dichloro-2-butene wherein the molar quantity of the difunctional tertiary amine is greater than the molar quantity of the monofunctional tertiary amine, and, (b) a polydiguanide; and, (2) 0.001 to 0.05 percent by weight of an oxidizing agent which has a standard reduction potential in the range defined by that of hydrogen peroxide, chlorine dioxide and hypochlorite, is soluble in water, non-toxic and, in said compositions, enhances the activity of said compound by oxidation in situ at low concentrations.
Claim 26
Dependent Claim 15 words
A method according to claim 22 in which the polymeric compound is polymeric hexamethylene diguanide.

References Cited (Backward Citations)

US3123521A Cited
US2917428A Cited
US3689673A Cited
US4029817A Cited
US4073888A Cited
US4026945A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-03-30 1990-09-29 1991-03-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-03-30 1994-09-29 1995-03-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-03-30 1998-09-29 1999-03-31 $7700.00 Window Closed / Lapsed

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