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US4496576A
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Compositions of p-hydroxybenzoic acid esters and methods of preparation and use
Assignee: Malco Inc
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Filing: 1983-09-12
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Granted: 1985-01-29
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Expires: 2003-09-12
Abstract
Abstract A composition having broad spectrum antimicrobial activity and being freeze and heat stable is comprised of a clear solution containing up to approximately 90% by weight of a eutectic mixture of three or more lower alkyl esters of p-hydroxybenzoic acid such as isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate in a ratio between approximately 1:1:1 to 4:2:2, respectively, approximately 10% to 90% by weight of a "Glydant" solution (composed of 55% 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% water) and at least approximately 0.5% by weight based on the weight of the eutectic mixture and the "Glydant" solution of an anionic surfactant. The latter, for example, may be dioctyl sodium sulfosuccinate, sodium lauryl sulfate or the ammonium or sodium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol.
Inventors
- 👤 Donald F. Loncrini
- 👤 Thomas E. Haag
- 👤 Steven R. Freebersyser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 21:25
CPC Classifications
A; A01; A01N; A01N37/00; A01N37/36; A01N37/38; A01N37/40; A01N43/00; A01N43/48; A01N43/50
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
77 words
A freeze and heat stable composition having broad spectrum antimicrobial activity consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of three or more lower alkyl esters of p-hydroxybenzoic acid, approximately 10% to 90% by weight of a solution containing 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 2
Dependent Claim
77 words
A freeze and heat stable composition having broad spectrum antimicrobial activity consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of three or more lower alkyl esters of p-hydroxybenzoic acid, approximately 10% to 90% by weight of a solution containing 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 3
Dependent Claim
35 words
A composition as set forth in claim 1 wherein said anionic surfactant is selected from the group consisting of dioctyl sodium sulfosuccinate, sodium lauryl sulfate and the ammonium or sodium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol.
Claim 4
Dependent Claim
50 words
A composition as set forth in claim 1 wherein said clear solution contains approximately 90% by weight of said eutectic mixture, approximately 10% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 6% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 5
Dependent Claim
50 words
A composition as set forth in claim 1 wherein said clear solution contains approximately 55% by weight of said eutectic mixture, approximately 45% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 7% by weight of sodium lauryl sulfate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 6
Dependent Claim
50 words
A composition as set forth in claim 1 wherein said clear solution contains aproximately 50% by weight of said eutectic mixture, approximately 50% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 10% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 7
Dependent Claim
54 words
A composition as set forth in claim 1 wherein said clear solution contains approximately 40% by weight of said eutectic mixture, approximately 60% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 5% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 8
Dependent Claim
54 words
A composition as set forth in claim 1 wherein said clear solution contains approximately 10% by weight of said eutectic mixture, approximately 90% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 2% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 9
Dependent Claim
36 words
A composition as set forth in claim 1 wherein said clear solution contains between approximately 2% and 10% by weight of said anionic surfactant based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 10
Dependent Claim
85 words
A freeze and heat stable composition having broad spectrum antimicrobial activity consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate in a ratio between approximately 1:1:1 and 4:2:2, respectively, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 11
Dependent Claim
85 words
A freeze and heat stable composition having broad spectrum antimicrobial activity consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate in a ratio between approximately 1:1:1 and 4:2:2, respectively, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 12
Dependent Claim
35 words
A composition as set forth in claim 9 wherein said anionic surfactant is selected from the group consisting of dioctyl sodium sulfosuccinate, sodium lauryl sulfate and the ammonium or sodium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol.
Claim 13
Dependent Claim
26 words
A composition as set forth in claim 9 wherein said eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate has a ratio of 4:2.5:2.5, respectively.
Claim 14
Dependent Claim
50 words
A composition as set forth in claim 9 wherein said clear solution contains approximately 90% by weight of said eutectic mixture, approximately 10% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 6% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 15
Dependent Claim
50 words
A composition as set forth in claim 9 wherein said clear solution contains approximately 55% by weight of said eutectic mixture, approximately 45% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 7% by weight of sodium lauryl sulfate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 16
Dependent Claim
50 words
A composition as set forth in claim 9 wherein said clear solution contains approximately 50% by weight of said eutectic mixture, approximately 50% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 10% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 17
Dependent Claim
54 words
A composition as set forth in claim 9 wherein said clear solution contains approximately 40% by weight of said eutectic mixture, approximately 60% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 5% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 18
Dependent Claim
54 words
A composition as set forth in claim 9 wherein said clear solution contains approximately 10% by weight of said eutectic mixture, approximately 90% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 2% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 19
Dependent Claim
36 words
A composition as set forth in claim 9 wherein said clear solution contains between approximately 2% and 10% by weight of said anionic surfactant based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 20
Independent Claim
97 words
A method of inhibiting antimicrocrobial activity of a microoganism selected from the group consisting of bacteria, yeast and fungi comprising contacting said microorganism with a freeze and heat stable composition consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of three or more lower alkyl esters of p-hydroxybenzoic acid, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 21
Independent Claim
97 words
A method of inhibiting antimicrocrobial activity of a microoganism selected from the group consisting of bacteria, yeast and fungi comprising contacting said microorganism with a freeze and heat stable composition consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of three or more lower alkyl esters of p-hydroxybenzoic acid, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 22
Dependent Claim
35 words
A method as set forth in claim 18 wherein said anionic surfactant is selected from the group consisting of dioctyl sodium sulfosuccinate, sodium lauryl sulfate and the ammonium or sodium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol.
Claim 23
Dependent Claim
50 words
A method as set forth in claim 18 wherein said clear solution contains approximately 90% by weight of said eutectic mixture, approximately 10% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 6% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 24
Dependent Claim
50 words
A method as set forth in claim 18 wherein said clear solution contains approximately 55% by weight of said eutectic mixture, approximately 45% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 7% by weight of sodium lauryl sulfate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 25
Dependent Claim
50 words
A method as set forth in claim 20 wherein said clear solution contains approximately 50% by weight of said eutectic mixture, approximately 50% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 10% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 26
Dependent Claim
54 words
A method as set forth in claim 20 wherein said clear solution contains approximately 40% by weight of said eutectic mixture, approximately 60% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 5% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 27
Dependent Claim
54 words
A method as set forth in claim 18 wherein said clear solution contains approximately 10% by weight of said eutectic mixture, approximately 90% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 2% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 28
Dependent Claim
36 words
A method as set forth in claim 18 wherein said clear solution contains between approximately 2% and 10% by weight of said anionic surfactant based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 29
Dependent Claim
26 words
A method as set forth in claim 18 wherein the minimum inhibitory concentration of said composition contacting said microorganism ranges between 32 ppm and 2000 ppm.
Claim 30
Independent Claim
104 words
A method of inhibiting antimicrobial activity of a microorganism selected from the group consisting of bacteria, yeast and fungi comprising contacting said microorganism with a freeze and heat stable composition consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate in a ratio between approximately 1:1:1 and 4:2:2, respectively, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 31
Independent Claim
104 words
A method of inhibiting antimicrobial activity of a microorganism selected from the group consisting of bacteria, yeast and fungi comprising contacting said microorganism with a freeze and heat stable composition consisting of a clear solution containing approximately 10% to 90% by weight of a eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate in a ratio between approximately 1:1:1 and 4:2:2, respectively, approximately 10% to 90% by weight of a solution containing approximately 55% of 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin and 45% of water, and approximately 0.5% to 10% by weight based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution of an anionic surfactant.
Claim 32
Dependent Claim
35 words
A method as set forth in claim 27 wherein said anionic surfactant is selected from the group consisting of dioctyl sodium sulfosuccinate, sodium lauryl sulfate and the ammonium or sodium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol.
Claim 33
Dependent Claim
26 words
A method as set forth in claim 27 wherein said eutectic mixture of isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate has a ratio of 4:2.5:2.5, respectively.
Claim 34
Dependent Claim
50 words
A method as set forth in claim 27 wherein said clear solution contains approximately 90% by weight of said eutectic mixture, approximately 10% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 6% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 35
Dependent Claim
50 words
A method as set forth in claim 27 wherein said clear solution contains approximately 55% by weight of said eutectic mixture, approximately 45% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 7% by weight of sodium lauryl sulfate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 36
Dependent Claim
50 words
A method as set forth in claim 27 wherein said clear solution contains approximately 50% by weight of said eutectic mixture, approximately 50% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 10% by weight of dioctyl sodium sulfosuccinate based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 37
Dependent Claim
54 words
A method as set forth in claim 27 wherein said clear solution contains approximately 40% by weight of said eutectic mixture, approximately 60% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantion solution and approximately 5% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 38
Dependent Claim
54 words
A method as set forth in claim 27 wherein said clear solution contains approximately 10% by weight of said eutectic mixture, approximately 90% by weight of said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution and approximately 2% by weight of the ammonium salt of sulfated nonylphenoxypoly(ethyleneoxy) ethanol based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 39
Dependent Claim
36 words
A method as set forth in claim 27 wherein said clear solution contains between approximately 2% and 10% by weight of said anionic surfactant based on the weight of said eutectic mixture and said 1,3-bis(hydroxymethyl)-5,5-dimethylhydantoin solution.
Claim 40
Dependent Claim
26 words
A method as set forth in claim 27 wherein the minimum inhibitory concentration of said composition contacting said microorganism ranges between 32 ppm and 2000 ppm.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-01-29 | 1988-07-30 | 1989-01-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-29 | 1992-07-30 | 1993-01-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-29 | 1996-07-30 | 1997-01-29 | $7700.00 | Window Closed / Lapsed |