US3069359A - Germicidal detergent composition - Google Patents

Germicidal detergent composition Download PDF

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Publication number
US3069359A
US3069359A US723943A US72394358A US3069359A US 3069359 A US3069359 A US 3069359A US 723943 A US723943 A US 723943A US 72394358 A US72394358 A US 72394358A US 3069359 A US3069359 A US 3069359A
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Prior art keywords
neomycin
ethylene oxide
moles
water
reaction product
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US723943A
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Blodinger Jack
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Wyeth Holdings LLC
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American Cyanamid Co
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T24/00—Buckles, buttons, clasps, etc.
    • Y10T24/14—Bale and package ties, hose clamps
    • Y10T24/1498—Plastic band

Definitions

  • This invention relates to a germicidal detergent composition containing neomycin.
  • Neomycin is a well-known antibiotic produced by propagation of microorganisms of the species Streptomyces fradiae as described in United States patent to Waksman No. 2,799,620. Attempts have been made to take advantage of the bacteriostatic properties of neornycin for topical application by incorporating the neomycin, usually as the sulfate, in various aqueous preparations such as soaps and the like. However, this proposal has met with difficulty because neomycin has a known stability range of from about pH 2 to about pH 9 and ordinary soap solutions have a hydrogen ion concentration well above pH 9. Consequently, the antibacterial properties of neomycin are destroyed in such solutions.
  • the present invention is predicated upon the discovery that if a small amount of a nonionic surface active agent is incorporated into the anionic detergent along with the neomycin, the neomycin is rendered stable and does not precipitate out on standing,
  • the present invention preferably embodies a germicidal detergent composition comprising from about to about of a water-soluble organic anionic detergent, a small but effective amount of neomycin usually from about 0.1 to about 3% (as the base), and from about 0.1 to about 2.0% of a nonionic surface active agent, the resulting composition having a pH of from about 5-7 so that the composition is virtually free of irritating effects on the skin.
  • the suitable anionic detergents are the watersoluble higher fatty acid soaps (cg. sodium lauryl sulfate, sodium salts of higher fatty acids derived from coconut oil, palm oil and tallow), and the sulfated and sulfonated organic detergents.
  • water soluble salts of higher alkyl aryl sulfonate eg. sodium dodecyibenzenesulfonate, sodium laurylbenzenesulfonate
  • higher alkyl sulfate detergent e.g.
  • higher fatty acids eg. sodium coconut monogylceride monosulfate
  • sulfated hi her fatty acid amides e.g. sodium lauric monoethanolamide sulfate
  • nonionic detergents are the polyalkylene oxide condensates with hydrophobic organic compounds, usually of an aliphatic or an aromatic structure.
  • suitable examples thereof are the higher alkyl aryl polyglycol ethers (cg. octylphenol or nonylphenol condensed with 6 to 30 moles ethylene oxide), organic acid esters with ethylene oxide (eg. tall oil esters with 6 to 30 moles of ethylene oxide), and alkyl aryl polyethylene glycol ethers of polypropylene glycol having a molecular weight of about 2,000 to 10,000, etc.
  • Particularly preferred surface active agents for use in the present invention are the nonionic octylphenoxyethanol series of com pounds sold under the trademark Triton, such as Triton X-100, Triton X-114 etc. and corresponding to the formula:
  • n is from 6-30.
  • Example 1 A germicidal detergent composition is prepared by dissolving 1.5 parts of neomycin sulfate in 40 parts by volume of water. 10 parts by volume of Triton X-l00 (reaction product of 9-10 moles of ethylene oxide with octylphenol) are added and the mixture stirred until clear. 10 parts by volume of Triton X-l l4 (reaction product of 7-8 moles of ethylene oxide with octylphenol), 20 parts by volume of triethanolamine lauryl sulfate and 2 parts of Lanogel 41 (a water-soluble derivative of lanolin) are added with stirring until the solution is clear. Sufficient water is added to make up parts by volume. A clear, sparkling yellow solution is obtained. The pH is adjusted to pH 6.0 with citric acid. The neomycin is compatible in this anionic detergent and nonionic detergent solutions and remains stable for severeal months at room temperature, and for two months at 42 C. or for one Week at 56 C.
  • Triton X-l00
  • Example 2 A germicidal detergent composition is prepared following the procedure of Example 1 except that 8 parts of lngepal 00-710 (nonylphenoxypolyoxyethylene) is "seal in place or" the Triton X-l00 used in Example 1.
  • the resulting germicidal detergent composition has substantially the same properties as the composition of Example 1 and is stable for relatively the same period.
  • Example 3 A germicidal detergent composition is prepared following [the procedure of Example 1 except that 10 parts of Tergitol-Nonionic XD (alkyl aryl polyethylene glycol ether) is used in place of the Triton X-100 used in Example l.
  • the resulting germicidal detergent composition has substantially the same properties as the composition of Example 1 and is stable for relatively the same period.
  • a clear sparkling germicidal detergent solution comprising from about 5 to about 40% of a water-soluble organic anionic detergent, a small but effective amount of a therapeutically effective form of neomycin equivalent to from about 0.1 to 3% neomycin calculated as the free base, and from about 0.1 to about 20% of a nonionic surface active agent selected from the group consisting of the reaction product of octylphenol with from 6 to 30 moles of ethylene oxide and the reaction product of nonylphenoi with from about 6 to 30 moles of ethylene oxide, the resulting clear sparkling solution having added sufficient non-toxic organic acid and water to have a pH of between about 5 and about 7 and total 100%.
  • composition of claim 1 in which the anionic detergent is triethanolamine lauryl sulfate.
  • a clear sparkling germicidal detergent solution consisting essentially of from about 5 to about 40% of triethanolamine lauryl sulfate, a small but effective amount of a therapeutically effective form of neomycin equivalent to from about 0.1 to 3% neomycin calculated as the free base, from about 0.1 to about 20% of a nonionic surface active agent selected from the group consisting of the reaction product of octylphenol With from 6 to 30 moles of ethylene oxide and the reaction product of nonylphenol with from about 6 to 30 moles of ethylene oxide, about 2% of a water-soluble derivative of lanolin, sufiicient citric acid to adjust the pH to between about 5 and about 7, and Water to a total of 100%, said solution being stable for at least two months at 42 C.

Description

3,009,359 Patented Dec. 18, 1962 3,069,359 GERl /HCHDAL DETERGENT IUWQSHEQN Jack Biodinger, Monsey, N.Y., assiguor to American (Zyanainid Company, New York, N311, a corporation of Maine No Drawing. Filed Mar. 26, 1953, Ser. No. 723,943 3 Claims. (61. 252-107) This invention relates to a germicidal detergent composition containing neomycin.
Neomycin is a well-known antibiotic produced by propagation of microorganisms of the species Streptomyces fradiae as described in United States patent to Waksman No. 2,799,620. Attempts have been made to take advantage of the bacteriostatic properties of neornycin for topical application by incorporating the neomycin, usually as the sulfate, in various aqueous preparations such as soaps and the like. However, this proposal has met with difficulty because neomycin has a known stability range of from about pH 2 to about pH 9 and ordinary soap solutions have a hydrogen ion concentration well above pH 9. Consequently, the antibacterial properties of neomycin are destroyed in such solutions. If the pH of the soap solution is lowered to any extent or if the neomycin is incorporated in conventional anionic detergents, it is founc. that the neomycin is incompatible with such detergents and a heavy precipitate occurs rendering the resultant composition useless as a germicidal cleaning composition.
The present invention is predicated upon the discovery that if a small amount of a nonionic surface active agent is incorporated into the anionic detergent along with the neomycin, the neomycin is rendered stable and does not precipitate out on standing, The present invention preferably embodies a germicidal detergent composition comprising from about to about of a water-soluble organic anionic detergent, a small but effective amount of neomycin usually from about 0.1 to about 3% (as the base), and from about 0.1 to about 2.0% of a nonionic surface active agent, the resulting composition having a pH of from about 5-7 so that the composition is virtually free of irritating effects on the skin.
Among the suitable anionic detergents are the watersoluble higher fatty acid soaps (cg. sodium lauryl sulfate, sodium salts of higher fatty acids derived from coconut oil, palm oil and tallow), and the sulfated and sulfonated organic detergents. Examples of the latter are water soluble salts of higher alkyl aryl sulfonate (eg. sodium dodecyibenzenesulfonate, sodium laurylbenzenesulfonate), higher alkyl sulfate detergent (e.g. sodium lauryl sulfate, potassium cetyl sulfate, triethanolamine lauryl sulfate, diethanolamine lauryl sulfate and ammonium lauryl sulfate), sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids (eg. sodium coconut monogylceride monosulfate), sulfated hi her fatty acid amides (e.g. sodium lauric monoethanolamide sulfate), etc.
Among the suitable nonionic detergents are the polyalkylene oxide condensates with hydrophobic organic compounds, usually of an aliphatic or an aromatic structure. Suitable examples thereof are the higher alkyl aryl polyglycol ethers (cg. octylphenol or nonylphenol condensed with 6 to 30 moles ethylene oxide), organic acid esters with ethylene oxide (eg. tall oil esters with 6 to 30 moles of ethylene oxide), and alkyl aryl polyethylene glycol ethers of polypropylene glycol having a molecular weight of about 2,000 to 10,000, etc. Particularly preferred surface active agents for use in the present invention are the nonionic octylphenoxyethanol series of com pounds sold under the trademark Triton, such as Triton X-100, Triton X-114 etc. and corresponding to the formula:
osuh-Q o crnonnnon and wherein n is from 6-30, and the nonylphenoxypolyoxyethylene compounds sold under the trademark Igepal corresponding to the formula:
OQHH-Q- O cutout) non wherein n is from 6-30.
The invention will be described in greater detail in conjunction with the following specific examples in which the parts are by weight unless otherwise specified.
Example 1 A germicidal detergent composition is prepared by dissolving 1.5 parts of neomycin sulfate in 40 parts by volume of water. 10 parts by volume of Triton X-l00 (reaction product of 9-10 moles of ethylene oxide with octylphenol) are added and the mixture stirred until clear. 10 parts by volume of Triton X-l l4 (reaction product of 7-8 moles of ethylene oxide with octylphenol), 20 parts by volume of triethanolamine lauryl sulfate and 2 parts of Lanogel 41 (a water-soluble derivative of lanolin) are added with stirring until the solution is clear. Sufficient water is added to make up parts by volume. A clear, sparkling yellow solution is obtained. The pH is adjusted to pH 6.0 with citric acid. The neomycin is compatible in this anionic detergent and nonionic detergent solutions and remains stable for severeal months at room temperature, and for two months at 42 C. or for one Week at 56 C.
Example 2 A germicidal detergent composition is prepared following the procedure of Example 1 except that 8 parts of lngepal 00-710 (nonylphenoxypolyoxyethylene) is "seal in place or" the Triton X-l00 used in Example 1. The resulting germicidal detergent composition has substantially the same properties as the composition of Example 1 and is stable for relatively the same period.
Example 3 A germicidal detergent composition is prepared following [the procedure of Example 1 except that 10 parts of Tergitol-Nonionic XD (alkyl aryl polyethylene glycol ether) is used in place of the Triton X-100 used in Example l. The resulting germicidal detergent composition has substantially the same properties as the composition of Example 1 and is stable for relatively the same period.
1 claim:
1. A clear sparkling germicidal detergent solution comprising from about 5 to about 40% of a water-soluble organic anionic detergent, a small but effective amount of a therapeutically effective form of neomycin equivalent to from about 0.1 to 3% neomycin calculated as the free base, and from about 0.1 to about 20% of a nonionic surface active agent selected from the group consisting of the reaction product of octylphenol with from 6 to 30 moles of ethylene oxide and the reaction product of nonylphenoi with from about 6 to 30 moles of ethylene oxide, the resulting clear sparkling solution having added sufficient non-toxic organic acid and water to have a pH of between about 5 and about 7 and total 100%.
2. The composition of claim 1 in which the anionic detergent is triethanolamine lauryl sulfate.
3. A clear sparkling germicidal detergent solution consisting essentially of from about 5 to about 40% of triethanolamine lauryl sulfate, a small but effective amount of a therapeutically effective form of neomycin equivalent to from about 0.1 to 3% neomycin calculated as the free base, from about 0.1 to about 20% of a nonionic surface active agent selected from the group consisting of the reaction product of octylphenol With from 6 to 30 moles of ethylene oxide and the reaction product of nonylphenol with from about 6 to 30 moles of ethylene oxide, about 2% of a water-soluble derivative of lanolin, sufiicient citric acid to adjust the pH to between about 5 and about 7, and Water to a total of 100%, said solution being stable for at least two months at 42 C.
References Cited in the file of this patent UNlTED STAT ES PATENTS 2,865,859 Lubowe Dec. 23, 1958 2,880,130 Johnson Mar. 31, 1959 2,880,138 Johnson Mar. 31, 1959 2,942,008 Lubowe June 21, 1960 4 Reed Jan, 17, 1961 Goyan et al. Mar. 14, 1961 Parlour Apr. 11, 1961 Cyr et a1 Apr. 10, 1962 FOREIGN PATENTS Great Britain Nov. 14, 1956 France Feb. 18, 1948 OTHER REFERENCES Heatley et al.: J. Gen. Microbiology, vol. 6, 1952, p.
J. Pharmacy, July 1952, p. 6243. Dale: J.A.P.A., Prac. Pharrn. Ed, July 1957, pp. 421- Livingood et al.:

Claims (1)

1. A CLEAR SPARKLING GERMICIDAL DETERGENT SOLUTION COMPRISING FROM ABOUT 5 TO ABOUT 40% OF A WATER-SOLUBLE ORGANIC ANIONIC DETERGENT, A SMALL BUT EFFECTIVE AMOUNT OF A THERAPEUTICALLY EFFECTIVE FROM OF NEOMYCIN EQUIVALENT TO FORM ABOUT 0.1 TO 3% NEOMYCIN CALCULATED AS THE FREE BASE, AND FROM ABOUT 0.1 TO ABOUT 20% OF A NONIONIC SURFACE ACTIVE AGENT SELECTED FROM THE GROUP CONSISTING OF THE REACTION PRODUCT OF OCTYLPHENOL WITH FROM 6 TO 30 MOLES OF ETHYLENE OXIDE AND THE REACTION PRODUCT OF NONYLPHENOL WITH FROM ABOUT 6 TO 30 MOLES OF ETHYLENE OXIDE, THE RESULTING CLEAR SPARKLING SOLUTION HAVING ADDED SUFFICIENT NON-TOXIC ORGANIC ACID AND WATER TO HAVE A PH OF BETWEEN ABOUT 5 TO ABOUT 7 AND TOTAL 100%.
US723943A 1958-03-26 1958-03-26 Germicidal detergent composition Expired - Lifetime US3069359A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3174905A (en) * 1962-03-12 1965-03-23 American Cyanamid Co Methods and compositions for rendering textile materials soft, germ resistant and antistatic
US3951841A (en) * 1972-06-08 1976-04-20 Discwasher Inc. Phonograph record cleaning composition
WO2005044965A1 (en) * 2003-11-10 2005-05-19 Schwarzwälder Marketing Gmbh & Co. Use of a solution comprising at least one nonionic surfactant

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR931270A (en) * 1945-02-10 1948-02-18 Sharp & Dohme Process for preparing bacteriostatic compositions
GB761269A (en) * 1953-04-24 1956-11-14 American Cyanamid Co Improvements in or relating to antiseptic detergent compositions and process of making the same
US2865859A (en) * 1956-11-09 1958-12-23 Irwin I Lubowe Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes
US2880138A (en) * 1956-12-24 1959-03-31 Upjohn Co Anti-inflammatory steroid solutions
US2880130A (en) * 1956-12-24 1959-03-31 Upjohn Co Anti-inflammatory steroid solutions
US2942008A (en) * 1956-12-10 1960-06-21 Irwin I Lubowe Solubilizing of mineral, vegetable, and animal oils for cosmetic, pharmaceutical, and industrial purposes
US2968628A (en) * 1958-10-17 1961-01-17 Shulton Inc Propellant composition
US2975099A (en) * 1958-06-25 1961-03-14 Upjohn Co Polyethylene glycol suppository bases
US2979410A (en) * 1957-05-13 1961-04-11 Tee Pak Inc Food package and packaging film therefor
US3029188A (en) * 1958-02-20 1962-04-10 Olin Mathieson Gelatin adhesive pharmaceutical preparations

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR931270A (en) * 1945-02-10 1948-02-18 Sharp & Dohme Process for preparing bacteriostatic compositions
GB761269A (en) * 1953-04-24 1956-11-14 American Cyanamid Co Improvements in or relating to antiseptic detergent compositions and process of making the same
US2865859A (en) * 1956-11-09 1958-12-23 Irwin I Lubowe Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes
US2942008A (en) * 1956-12-10 1960-06-21 Irwin I Lubowe Solubilizing of mineral, vegetable, and animal oils for cosmetic, pharmaceutical, and industrial purposes
US2880138A (en) * 1956-12-24 1959-03-31 Upjohn Co Anti-inflammatory steroid solutions
US2880130A (en) * 1956-12-24 1959-03-31 Upjohn Co Anti-inflammatory steroid solutions
US2979410A (en) * 1957-05-13 1961-04-11 Tee Pak Inc Food package and packaging film therefor
US3029188A (en) * 1958-02-20 1962-04-10 Olin Mathieson Gelatin adhesive pharmaceutical preparations
US2975099A (en) * 1958-06-25 1961-03-14 Upjohn Co Polyethylene glycol suppository bases
US2968628A (en) * 1958-10-17 1961-01-17 Shulton Inc Propellant composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3174905A (en) * 1962-03-12 1965-03-23 American Cyanamid Co Methods and compositions for rendering textile materials soft, germ resistant and antistatic
US3951841A (en) * 1972-06-08 1976-04-20 Discwasher Inc. Phonograph record cleaning composition
WO2005044965A1 (en) * 2003-11-10 2005-05-19 Schwarzwälder Marketing Gmbh & Co. Use of a solution comprising at least one nonionic surfactant
US20070093405A1 (en) * 2003-11-10 2007-04-26 Ursula Maier Use of a solution comprising at least one nonionic surfactant

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