US2795554A - Antiseptic soap composition - Google Patents

Antiseptic soap composition Download PDF

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Publication number
US2795554A
US2795554A US283491A US28349152A US2795554A US 2795554 A US2795554 A US 2795554A US 283491 A US283491 A US 283491A US 28349152 A US28349152 A US 28349152A US 2795554 A US2795554 A US 2795554A
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US
United States
Prior art keywords
detergent
soap
antiseptic
beta
benzoyl
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Expired - Lifetime
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US283491A
Inventor
Roland S Shumard
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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Priority to US283491A priority Critical patent/US2795554A/en
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Classifications

    • 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
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/26—Organic compounds, e.g. vitamins containing oxygen

Definitions

  • R is an aromatic hydrocarbon radical such as phenyl, tolyl, ethyl henyl, n-propylphenyl, cumyl, nbutylphenyl, tert. butylphenyl, n-amylphenyl, sec. amylpheny Y h XyDP Y xyly cymy t y phenyl, triethylphenyl, cyclohexylphenyl, benzylphenyl, phenethylpheny-l, biphenyl, naphthyl, etc. and where A is hydrogen or an alkali metal or an aliphatic radical when admixed with a detergent composition in minor proportions forms .a deter-gent product exhibiting excellent antiseptic properties.
  • antiseptic agents for purposes of this application the .bctaearyloyl acrylic acids, salts and esters thereof are termed antiseptic agents hereinafter.
  • the antiseptic agents of this invention are readily incorporated in detergent compositions whether the latter be solid or liquid.
  • the new antiseptic agents are nonvolatile and remain permanently in the detergent composition. They do not affect the lathering, cleansing or physical properties of the detergent nor do they impart any unpleasant odors nor discolor the finished detergent composition.
  • detergent containing compositions are prepared by intimately mixing the ingredients listed below to form a composite containing 2% by weight active ingredient.
  • A (parts by weight) "Ivory brand neutral white high grade toilet soap (a mixture of 80% sodium soap and potassium soap produced from a 70% tallow and 30% coconut oil glycerlde blend in accordance with U. S. 2,295,594)
  • Methyl beta-benzoyl acrylate 2 noted below:
  • Table 1 Composition A B Growth no growth-.- no growth.
  • composition A upon further dilution with nutrient agar so as to give a composition having a concentration of 1 p. p. m. (1:1,000,000) of active ingredient upon being streak wi h a .24 hour old culture of Salmonella typhosa of st nd r resistance after incubation at 37 C. for 72 ou xh bi ed no signsot acterial growth.
  • Beta-(p-phenyl-benzoyl) acrylic acid 2 Table II Composition ..l O l D Growth no growth... no growth.
  • Ethyl beta-benzoyl acrylate Isopropyl beta-benzoyl acrylate Sec. amyl beta-benzoyl acrylate n-Octyl beta-benzoyl acrylate Methyl beta-(p-methyl-benzoyl) acrylate Methyl beta-(p-isopropyl-benzoyl) acrylate Ethyl beta-(p-phenyl-benzoyl) acrylate Sodium beta-(p-phenyl-benzoyl) acrylate Potassium beta-(p-phenyl-benzoyl) acrylate Methyl beta-(p-phenyl-benzoyl) acrylate Beta-naphthoyl acrylic acid and evaluating in the same manner satisfactory controlof M icrococcus pyogenes var.
  • amounts in the order of 13% by weight While larger amounts may be employed, as for example up tol0% by weight based upon the weight of the detergent, the upper limit will be determined by practical consideration.
  • Other antiseptic agents may be incorporated as well as emollients, water softeners and the well-known vehicles of the soap trade.
  • Various colors, antioxidants, perfumes and the like may be included where desirable.
  • detergent includes soap and the synthetic detergents such as the Turkey red oils, the highly sul-V fonated fatty acids and the sulfated fatty alcohols.
  • detergent includes also mixtures of synthetic detergents and soap.
  • soap or detergent soap as used herein is employed in its popular or ordinary meaning-that is, those cleansing compositions, namely the wellknown washing toilet and liquid soaps prepared from an alkali metal compound such as sodium or potassium hydroxide and a fat or fatty acid.
  • the antiseptic agents of this'invention may be added to .the detergent compositions during the crutching or melting or similar operation.
  • the new antiseptic agents may be first dissolved in a suitable solvent and then incorporated in the detergent if so desired. In general, any method which results in the new antiseptic agent of this invention being uniformly incorporated in the final composition is satisfactory.
  • An antiseptic detergent composition comprising a detergent soap and 0.5 to 10% by weight based upon the detergent soap of a compound of the formula where R is an aromatic hydrocarbon radical containing not more than 14 carbon atoms and where A is selected from the group consisting of hydrogen, sodium, potassium and alkyl radicals containing not more than 8 carbon atoms.
  • Wll616'R is a benzenoid ydrocarbon radical and where A is a short chain alkyl radical.
  • An antiseptic detergent. soap composition comprising a detergent soap and 13% by weight based upon the detergent soap of beta-benzoyl acrylic acid.
  • An antiseptic detergent soap composition comprising a detergentso'ap and 14% by weight based upon the detergent soap of sodium beta-benzoyl-acrylate.
  • An antiseptic detergent soap composition comprising a detergent soap and l 3%-by weight based upon the detergent soap of methyl beta-benzoyl acrylate.
  • An antiseptic detergent soap composition comprising a detergent soap and 1-3% by weight based upon the detergent soap of ethyl beta-benzoyl acrylate.
  • An antiseptic detergent soap composition comprising a detergent soap and 1-3% by weight based upon the detergent .soap of beta-(p-phenyl-benzoyl) acrylic acid.

Description

United St ANTISEPTIC SOAP COMPOSITION Roland S. Shumard, Brentwood, Mo., assignor to Monsanto Chemical Company, St. Louis; MoJa corporation of Delaware N Drawing. Application April 21, 1952, Serial No. 283,491
7 Claims. (Cl. 252-107) where R is an aromatic hydrocarbon radical such as phenyl, tolyl, ethyl henyl, n-propylphenyl, cumyl, nbutylphenyl, tert. butylphenyl, n-amylphenyl, sec. amylpheny Y h XyDP Y xyly cymy t y phenyl, triethylphenyl, cyclohexylphenyl, benzylphenyl, phenethylpheny-l, biphenyl, naphthyl, etc. and where A is hydrogen or an alkali metal or an aliphatic radical when admixed with a detergent composition in minor proportions forms .a deter-gent product exhibiting excellent antiseptic properties.
For purposes of this application the .bctaearyloyl acrylic acids, salts and esters thereof are termed antiseptic agents hereinafter.
The antiseptic agents of this invention are readily incorporated in detergent compositions whether the latter be solid or liquid. The new antiseptic agents are nonvolatile and remain permanently in the detergent composition. They do not affect the lathering, cleansing or physical properties of the detergent nor do they impart any unpleasant odors nor discolor the finished detergent composition.
As exemplary of this invention, detergent containing compositions are prepared by intimately mixing the ingredients listed below to form a composite containing 2% by weight active ingredient.
B Composition (parts by weight) A (parts by weight) "Ivory brand neutral white high grade toilet soap (a mixture of 80% sodium soap and potassium soap produced from a 70% tallow and 30% coconut oil glycerlde blend in accordance with U. S. 2,295,594)
Beta-benzoyl acrylic acid t. 2
Methyl beta-benzoyl acrylate 2 noted below:
Table 1 Composition A B Growth no growth-.- no growth.
i P r 0" 7 Patented June 11, 1957 Composition A upon further dilution with nutrient agar so as to give a composition having a concentration of 1 p. p. m. (1:1,000,000) of active ingredient upon being streak wi h a .24 hour old culture of Salmonella typhosa of st nd r resistance after incubation at 37 C. for 72 ou xh bi ed no signsot acterial growth.
Replacing either of the respective antiseptic agents of Compositions A and 3 above with any one .oi the tollowing;
- positions areprepared gby intimately mixing the ingredi- Zem's listed helm mposite containing 2% by weightyiacfive nt.
' C D compilation (parts1hy (parts by w i ht) weight) Ivor-y brand neutral white high grade toilet soap (a mixture of sodium soap and 20% potassium :soap produced from a 70% .tallow and 30% coconut oil glyoeride blend in accord ance with U. S. 2,295,594) 98 98 Methyl beta-benaoylacrylate .l. 2
Beta-(p-phenyl-benzoyl) acrylic acid 2 Table II Composition ..l O l D Growth no growth... no growth.
Replacing the respective antiseptic agents of Compositions C and D above with any one of the following:
Ethyl beta-benzoyl acrylate Isopropyl beta-benzoyl acrylate Sec. amyl beta-benzoyl acrylate n-Octyl beta-benzoyl acrylate Methyl beta-(p-methyl-benzoyl) acrylate Methyl beta-(p-isopropyl-benzoyl) acrylate Ethyl beta-(p-phenyl-benzoyl) acrylate Sodium beta-(p-phenyl-benzoyl) acrylate Potassium beta-(p-phenyl-benzoyl) acrylate Methyl beta-(p-phenyl-benzoyl) acrylate Beta-naphthoyl acrylic acid and evaluating in the same manner satisfactory controlof M icrococcus pyogenes var. aureus is obtained. 7 In th control of Micrococcas 3 pyogenes var. aureus compounds of the formula -ficient. antiseptic detergent compositions. Amounts as low as 0.5 to 1% by weight based upon the weight of Where A is a short-chain alkyl radical and where R is a the detergent have proved satisfactory in-some instances.
However, it is preferred to employ amounts in the order of 13% by weight. While larger amounts may be employed, as for example up tol0% by weight based upon the weight of the detergent, the upper limit will be determined by practical consideration. Other antiseptic agents may be incorporated as well as emollients, water softeners and the well-known vehicles of the soap trade. Various colors, antioxidants, perfumes and the like may be included where desirable.
The term detergent includes soap and the synthetic detergents such as the Turkey red oils, the highly sul-V fonated fatty acids and the sulfated fatty alcohols. The term detergent includes also mixtures of synthetic detergents and soap. The term soap or detergent soap as used herein is employed in its popular or ordinary meaning-that is, those cleansing compositions, namely the wellknown washing toilet and liquid soaps prepared from an alkali metal compound such as sodium or potassium hydroxide and a fat or fatty acid.
The antiseptic agents of this'inventionmay be added to .the detergent compositions during the crutching or melting or similar operation. The new antiseptic agents may be first dissolved in a suitable solvent and then incorporated in the detergent if so desired. In general, any method which results in the new antiseptic agent of this invention being uniformly incorporated in the final composition is satisfactory.
.What is claimed is: A
1. An antiseptic detergent composition comprising a detergent soap and 0.5 to 10% by weight based upon the detergent soap of a compound of the formula where R is an aromatic hydrocarbon radical containing not more than 14 carbon atoms and where A is selected from the group consisting of hydrogen, sodium, potassium and alkyl radicals containing not more than 8 carbon atoms.
2. An antiseptic detergent composition comprising a detergent soap and 1-3% by weight based upon the detergent soap of a compound of the formula R. ;.-cn=cn-oo.'0n
Wll616'R is a benzenoid ydrocarbon radical and where A is a short chain alkyl radical. a
3. An antiseptic detergent. soap composition comprising a detergent soap and 13% by weight based upon the detergent soap of beta-benzoyl acrylic acid.
4. An antiseptic detergent soap composition comprising a detergentso'ap and 14% by weight based upon the detergent soap of sodium beta-benzoyl-acrylate.
5. An antiseptic detergent soap composition comprising a detergent soap and l 3%-by weight based upon the detergent soap of methyl beta-benzoyl acrylate.
6. An antiseptic detergent soap composition comprising a detergent soap and 1-3% by weight based upon the detergent soap of ethyl beta-benzoyl acrylate.
I 7. An antiseptic detergent soap composition comprising a detergent soap and 1-3% by weight based upon the detergent .soap of beta-(p-phenyl-benzoyl) acrylic acid.
References Cited in the file of this patent ,UNITED STATES PATENTS 2,251,935 Hartung Aug. 12, 1941

Claims (1)

  1. 2. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING A DETERGENT SOAP AND 1-3% BY WEIGHT BASED UPON THE DETERGENT SOAP OF A COMPOUND OF THE FORMULA
US283491A 1952-04-21 1952-04-21 Antiseptic soap composition Expired - Lifetime US2795554A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3020237A (en) * 1957-10-25 1962-02-06 Lyman D Dunn Cleansing composition in dry granular form
US3133119A (en) * 1961-11-09 1964-05-12 Givaudan Corp Substituted acetanilides and propionanilides
US3179596A (en) * 1960-05-20 1965-04-20 Colgate Palmolive Co Soap bar for dry skin
US4154817A (en) * 1974-07-02 1979-05-15 Kao Soap Co., Ltd. Smell-removing and deodorizing composition and process of using same
US4473583A (en) * 1981-10-22 1984-09-25 Roussel Uclaf Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2251935A (en) * 1936-09-21 1941-08-12 Sharp & Dohme Inc Germicidal soap

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2251935A (en) * 1936-09-21 1941-08-12 Sharp & Dohme Inc Germicidal soap

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3020237A (en) * 1957-10-25 1962-02-06 Lyman D Dunn Cleansing composition in dry granular form
US3179596A (en) * 1960-05-20 1965-04-20 Colgate Palmolive Co Soap bar for dry skin
US3133119A (en) * 1961-11-09 1964-05-12 Givaudan Corp Substituted acetanilides and propionanilides
US4154817A (en) * 1974-07-02 1979-05-15 Kao Soap Co., Ltd. Smell-removing and deodorizing composition and process of using same
US4473583A (en) * 1981-10-22 1984-09-25 Roussel Uclaf Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them

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