US3284363A - Germicidal soaps - Google Patents

Germicidal soaps Download PDF

Info

Publication number
US3284363A
US3284363A US471475A US47147565A US3284363A US 3284363 A US3284363 A US 3284363A US 471475 A US471475 A US 471475A US 47147565 A US47147565 A US 47147565A US 3284363 A US3284363 A US 3284363A
Authority
US
United States
Prior art keywords
soap
germicidal
mixture
synergistic
bars
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US471475A
Inventor
Willard M Bright
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lever Brothers Co
Original Assignee
Lever Brothers Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lever Brothers Co filed Critical Lever Brothers Co
Priority to US471475A priority Critical patent/US3284363A/en
Application granted granted Critical
Publication of US3284363A publication Critical patent/US3284363A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • the present invention relates to soap compositions, and more particularly to germicidal soap bars.
  • Soap bars are effective in their cleansing properties, but they have no germicidal activity so that they are ineffective in killing skin bacteria.
  • 34,S-tribromosalicylanilide When small amounts of 3,4,S-tribromosalicylanilide are incorporated into soap bars, there are produced bars having high germicidal activity. Such bars, however, are cream colored rather than pure white. While this discoloration of the soap bars may be accepted by some consumers, it is objectionable to many consumers who want to purchase white soap bars which have germicidal properties.
  • 3,4,4'-trichlorocarbanilide at low levels is incorporated into soap bars, the resulting bars have only very slight germicidal activity.
  • germicidal soap bars can be produced having a satisfactorily high germicidal activity even though they contain little of 3,4,5-tribromosalicylanilide, provided the bars contain both 3,4,5-tribromosalicylanilide and 3,4,4-trichlorocarbanilide. I have .further found quite unexpectedly that this mixture of germicides has synergistic germicidal activity in soap bars but not in non-soap bars.
  • soap bars containing both 3,4,S-tribromosalicylanilide and 3,4,4-trichlorocarbanilide have a germicidal activity which is higher than the sum of the activities of soap bars containing either of these germicides alone in the same amount as present in soap bars containing both of these germicides.
  • This synergistic effect has been observed over all ranges of relative amounts of these two germicides in the synergistic germicidal mixture.
  • germicidal soap bars can be produced having synergistic germicidal properties and. yet being substantially as white as soap bars which do not contain any germicide therein, provided certain relative proportions of the two germicides are present in the synergistic germicidal mixture as further described below'
  • the soap bars of the invention contain any watersolu-ble alkali metal soap.
  • Typical of these are the watersoluble alkali metal, e.g., potassium and sodium, soaps of the saturated and unsaturated higher fatty acids having from about eight to about twenty-six carbon atoms, such as capric, caprylic, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, arachidic, behenic, marigaric, tridechoic, and cerotic acids and the mixtures of such acids naturally occurring in fats, oils, waxes and rosins, such as the soaps of coconut oil fatty acids, tallow fatty acids, pig fat, fish oil fatty acids, beeswax, palm oil fatty acids, sesame oil fatty acids, peanut oil fatty acids, olive oil fatty acids, palm kernel oil fatty acids, cottonseed oil fatty acids, soyabean oil fatty acids, corn oil fatty acids, babassu oil fatty acids, rosin acids, abietic acid and
  • the soap bars also contain a synergistic germicidal mixture of 3,4,5 tribromosalicylanilide and 3.4.4-trichlorocarbanilide.
  • the total amount of the synergistic germicidal mixture is generally from about 0.1% to about 0.5%, and preferably from about 0.3% to about 0.5%, by weight of the soap. However, if desired, lesser total amounts of the two germicides can be employed, although this would cause a decrease in the germicidal activity of the soap bar. Larger total amounts of the two germicides can also be employed, for example 2% by weight of the soap, if desired. Such larger total amounts are usually not used because they increase the cost of the soap bars as well as possibly causing skin irritation.
  • the two germicides in the synergistic germicidal mixture can be present therein in any relative amounts, since all relative proportions have shown synergistic germicidal activity.
  • the synergistic germicidal mixture is made up of from about 40% to about 10% by weight of the mixture of 3.4',5- tribromosalicylanilide and from about 60% to about 90% respectively by weight of the mixture of 3,4,4'-t-richlorocarbanilide.
  • the use of such relative proportions results in the formation of soap bars which not only show synergistic germicidal activity, but also which are substantially as white as the same soap bars without the synergistic germicidal mixture therein.
  • the most desirable relative proportions of these two germicides in order to produce synergistic germicidal activity as well as substantially white soap bars are from about 35% to about 20% by weight of the mixture of 3,4,S-tribromosalicylanilide and from about 65% to about respectively by Weight of the mixture of 3,4,4-trichlorocarbanilide.
  • the soap bar may also contain compatible adjuvants which do not materially interfere with the synergistic germicidal activity of the bars.
  • compatible adjuvants are perfumes and various fillers.
  • the soap bars are prepared in the conventional manner. For example, soap chips are weighed into -a mixer and the compatible adjuvants, if any, added thereto and mixed therewith for a long enough period to insure uniform mixing. The two germicides are then added to the mixer and the mixing continued to insure uniformity of the mix. The final mix can then be formed into frame or milled soap bars in accordance with the general procedure of the soapmaking art.
  • the germicidal effectiveness of the soap bars of the invention was determined by a standardized test, namely the Finger Imprint Test. This test measures the inhibitory effect of an 8% solution (basis soap weight) of the germicidal soap bar being tested.
  • agar plates For use in the test, cultures of Micrococcus pyogenes var. aureus are maintained on nutrient broth with transfers made daily.
  • 0.1 milliliter of a 24 hour nutrient broth culture of the test organism is mixed thoroughly into 15 milliliters of melted nutrient agar, which is then poured into a Petri plate and permitted to harden.
  • the fingers of the subject's hand are immersed in small beakers containing 8% solutions of the germicidal soap bar in question. The fingers are thoroughly rinsed with water, dried and then placed lightly for thirty seconds on the agar plate. The plates are incubated overnight, and the contacted areas examined for absence of bacterial growth.
  • a sharply outlined clear zone is given a rating of 4, a clear area with a hazy periphery is rated 3, a hazy but perceptible imprint 2, a barely perceptible imprint l, and no detectable imprint 0. Intermediate ratings are designated by decimal units. Thus, the lower the numerical rating, the less effective the bactericide.
  • Germicidal soap bars were prepared containing various amounts of the synergistic germicidal mixture and various relative amounts of the two germicidal components thereof as shown by the data in the two tables set forth below.
  • the soap component in these bars was a mixture of 80% Table I Example No. Percent TBS Percent TCC Finger Imprint Rating When Example 213 containing the synergistic germicidal mixture is compared with Examples 2 and 2A containing either germicidal component alone in the same amounts as present in the germicidal mixture, synergism is amply shown.
  • Example 2B had synergistic germicidal activity, it was cream colored and would not be acceptable to those consumers who consider discoloration of soap bars to be objectionable.
  • Example 3B When Example 3B is compared with Examples 3 and 3A, synergistic germicidal activity of an extremely high nature is shown. Thus Example 3B had a finger imprint rating of 1.9, whereas the expected finger imprint rating thereof was the total rating of Examples 3 and 3A, namely 0.2 plus 0.1 or a total of 0.3.
  • Example 3B is representative of the preferred embodiment of the invention and was a soap bar which was substantially as white as the same soap bar without the synergistic germicidal mixture therein.
  • the synergistic germicidal activity of the soap bars of the invention is further demonstrated by the comparative data set forth in Table II below wherein the total of the synergistic mixture was 0.5% by weight of the soap.
  • Example 6B of the invention is compared with Examples 6 and 6A, and also when Example 7B of the invention is compared with Examples 7 and 7A, the synergistic germicidal activity of the soap bars is clearly shown.
  • the bars of Examples 63 and 7B were cream colored.
  • Example 8B A comparison of Example 8B with Examples 8 and 8A and a comparison of Example 9B with Examples 9 and 9A show extremely high synergistic germicidal activities of these two preferred embodiments of the invention.
  • the soap bar of Example 8B had a finger imprint rating of 3.3
  • the expected finger imprint rating was the total finger imprint rating of Examples 8 and 8A, namely 0.2 plus 0.4 or a total of 0.6.
  • the preferred embodiments of the invention illustrated by Examples 8B and 9B were soap bars which were substantially as white as the same soap bars without the synergistic mixture therein.
  • a germicidal soap composition consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5% by weight of the soap of a synergistic germicidal mixture of from about 40% to about 10% by weight of the mixture of 3,4,S-tribromosalicylanilide and from about 60% to about 90% respectively by weight of 3,4,4'-trichlorocarbanilide; said composition being substantially as white as the same composition without said synergistic mixture therein.
  • a germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5 by weight of the soap of a synergistic germicidal mixture of from about 40% to about 10% by weight of said mixture of 3,4,5-tribromosalicylanilide and from about 60% to about 90% respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.
  • a germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5% by weight of the soap of a synergistic germicidal mixture of from about 35% to about 20% by weight of said mixture of 3,4,S-tribromosalicylanilide and from about 65 to about respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.
  • a germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.3% to about 0.5 by weight of the soap of a synergistic germicidal mixture of from about 35% to about 20% by weight of said mixture of 3,4,S-tribromosalicylanilide and from about 65% to about 80% respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Patented Nov. 8, 1966 3,284,363 GERMICIDAL SOAPS Willard M. Bright, Winston-Salem, N.C., assignor to Lever Brothers Company, New York, N.Y., a corporation of Maine No Drawing. Continuation of application Ser. No. 3%,751, June 27, 1960. This application July 12, 1965, Ser. No. 471,475
4 Claims. (Cl. 252107) This application is a continuation of my copending application Serial No. 38,751, filed June 27, 1960, and now abandoned.
The present invention relates to soap compositions, and more particularly to germicidal soap bars.
Soap bars are effective in their cleansing properties, but they have no germicidal activity so that they are ineffective in killing skin bacteria. When small amounts of 3,4,S-tribromosalicylanilide are incorporated into soap bars, there are produced bars having high germicidal activity. Such bars, however, are cream colored rather than pure white. While this discoloration of the soap bars may be accepted by some consumers, it is objectionable to many consumers who want to purchase white soap bars which have germicidal properties. On the other hand, when 3,4,4'-trichlorocarbanilide at low levels is incorporated into soap bars, the resulting bars have only very slight germicidal activity.
I have found that germicidal soap bars can be produced having a satisfactorily high germicidal activity even though they contain little of 3,4,5-tribromosalicylanilide, provided the bars contain both 3,4,5-tribromosalicylanilide and 3,4,4-trichlorocarbanilide. I have .further found quite unexpectedly that this mixture of germicides has synergistic germicidal activity in soap bars but not in non-soap bars. That is to say soap bars containing both 3,4,S-tribromosalicylanilide and 3,4,4-trichlorocarbanilide have a germicidal activity which is higher than the sum of the activities of soap bars containing either of these germicides alone in the same amount as present in soap bars containing both of these germicides. This synergistic effect has been observed over all ranges of relative amounts of these two germicides in the synergistic germicidal mixture.
I have also found quite unexpectedly that germicidal soap bars can be produced having synergistic germicidal properties and. yet being substantially as white as soap bars which do not contain any germicide therein, provided certain relative proportions of the two germicides are present in the synergistic germicidal mixture as further described below' The soap bars of the invention contain any watersolu-ble alkali metal soap. Typical of these are the watersoluble alkali metal, e.g., potassium and sodium, soaps of the saturated and unsaturated higher fatty acids having from about eight to about twenty-six carbon atoms, such as capric, caprylic, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, arachidic, behenic, marigaric, tridechoic, and cerotic acids and the mixtures of such acids naturally occurring in fats, oils, waxes and rosins, such as the soaps of coconut oil fatty acids, tallow fatty acids, pig fat, fish oil fatty acids, beeswax, palm oil fatty acids, sesame oil fatty acids, peanut oil fatty acids, olive oil fatty acids, palm kernel oil fatty acids, cottonseed oil fatty acids, soyabean oil fatty acids, corn oil fatty acids, babassu oil fatty acids, rosin acids, abietic acid and. greases.
The soap bars also contain a synergistic germicidal mixture of 3,4,5 tribromosalicylanilide and 3.4.4-trichlorocarbanilide. The total amount of the synergistic germicidal mixture is generally from about 0.1% to about 0.5%, and preferably from about 0.3% to about 0.5%, by weight of the soap. However, if desired, lesser total amounts of the two germicides can be employed, although this would cause a decrease in the germicidal activity of the soap bar. Larger total amounts of the two germicides can also be employed, for example 2% by weight of the soap, if desired. Such larger total amounts are usually not used because they increase the cost of the soap bars as well as possibly causing skin irritation.
As noted above, the two germicides in the synergistic germicidal mixture can be present therein in any relative amounts, since all relative proportions have shown synergistic germicidal activity. In accordance with the preferred embodiment of the invention, however, the synergistic germicidal mixture is made up of from about 40% to about 10% by weight of the mixture of 3.4',5- tribromosalicylanilide and from about 60% to about 90% respectively by weight of the mixture of 3,4,4'-t-richlorocarbanilide. The use of such relative proportions results in the formation of soap bars which not only show synergistic germicidal activity, but also which are substantially as white as the same soap bars without the synergistic germicidal mixture therein. The most desirable relative proportions of these two germicides in order to produce synergistic germicidal activity as well as substantially white soap bars are from about 35% to about 20% by weight of the mixture of 3,4,S-tribromosalicylanilide and from about 65% to about respectively by Weight of the mixture of 3,4,4-trichlorocarbanilide.
If desired, the soap bar may also contain compatible adjuvants which do not materially interfere with the synergistic germicidal activity of the bars. Typical of such compatible adjuvants are perfumes and various fillers.
The soap bars are prepared in the conventional manner. For example, soap chips are weighed into -a mixer and the compatible adjuvants, if any, added thereto and mixed therewith for a long enough period to insure uniform mixing. The two germicides are then added to the mixer and the mixing continued to insure uniformity of the mix. The final mix can then be formed into frame or milled soap bars in accordance with the general procedure of the soapmaking art.
The germicidal effectiveness of the soap bars of the invention was determined by a standardized test, namely the Finger Imprint Test. This test measures the inhibitory effect of an 8% solution (basis soap weight) of the germicidal soap bar being tested.
For use in the test, cultures of Micrococcus pyogenes var. aureus are maintained on nutrient broth with transfers made daily. In preparing the agar plates, 0.1 milliliter of a 24 hour nutrient broth culture of the test organism is mixed thoroughly into 15 milliliters of melted nutrient agar, which is then poured into a Petri plate and permitted to harden. The fingers of the subject's hand are immersed in small beakers containing 8% solutions of the germicidal soap bar in question. The fingers are thoroughly rinsed with water, dried and then placed lightly for thirty seconds on the agar plate. The plates are incubated overnight, and the contacted areas examined for absence of bacterial growth. A sharply outlined clear zone is given a rating of 4, a clear area with a hazy periphery is rated 3, a hazy but perceptible imprint 2, a barely perceptible imprint l, and no detectable imprint 0. Intermediate ratings are designated by decimal units. Thus, the lower the numerical rating, the less effective the bactericide.
The invention will be further illustrated by the following comparative examples.
Germicidal soap bars were prepared containing various amounts of the synergistic germicidal mixture and various relative amounts of the two germicidal components thereof as shown by the data in the two tables set forth below. The soap component in these bars was a mixture of 80% Table I Example No. Percent TBS Percent TCC Finger Imprint Rating When Example 213 containing the synergistic germicidal mixture is compared with Examples 2 and 2A containing either germicidal component alone in the same amounts as present in the germicidal mixture, synergism is amply shown. Thus the finger imprint rating of Example 2B was 2.1 whereas the expected finger imprint rating for Example 2B was the total finger imprint rating of Example 2 plus Example 2A, namely 1.6 plus 0.1 or a total of 1.7. While Example 2B had synergistic germicidal activity, it was cream colored and would not be acceptable to those consumers who consider discoloration of soap bars to be objectionable.
When Example 3B is compared with Examples 3 and 3A, synergistic germicidal activity of an extremely high nature is shown. Thus Example 3B had a finger imprint rating of 1.9, whereas the expected finger imprint rating thereof was the total rating of Examples 3 and 3A, namely 0.2 plus 0.1 or a total of 0.3. Example 3B is representative of the preferred embodiment of the invention and was a soap bar which was substantially as white as the same soap bar without the synergistic germicidal mixture therein.
The synergistic germicidal activity of the soap bars of the invention is further demonstrated by the comparative data set forth in Table II below wherein the total of the synergistic mixture was 0.5% by weight of the soap.
When Example 6B of the invention is compared with Examples 6 and 6A, and also when Example 7B of the invention is compared with Examples 7 and 7A, the synergistic germicidal activity of the soap bars is clearly shown. The bars of Examples 63 and 7B were cream colored.
A comparison of Example 8B with Examples 8 and 8A and a comparison of Example 9B with Examples 9 and 9A show extremely high synergistic germicidal activities of these two preferred embodiments of the invention. Thus, the soap bar of Example 8B had a finger imprint rating of 3.3, whereas the expected finger imprint rating was the total finger imprint rating of Examples 8 and 8A, namely 0.2 plus 0.4 or a total of 0.6. The preferred embodiments of the invention illustrated by Examples 8B and 9B were soap bars which were substantially as white as the same soap bars without the synergistic mixture therein.
It will be appreciated that various modifications and changes may be made in the invention without departing from the spirit thereof, and accordingly the invention is to be limited only by the scope of the appended claims.
While the invention has been described in terms of soap bars, which are the preferred embodiment, it is equally applicable to soap powders, flakes, and liquids in which excellent germicidal activity without discoloration is desired. If such products are designed to be used at greater dilutions than those at which soap bars are normally used, the percentage of the germicidal mixture of the invention can be proportionately increased.
I claim:
1. A germicidal soap composition consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5% by weight of the soap of a synergistic germicidal mixture of from about 40% to about 10% by weight of the mixture of 3,4,S-tribromosalicylanilide and from about 60% to about 90% respectively by weight of 3,4,4'-trichlorocarbanilide; said composition being substantially as white as the same composition without said synergistic mixture therein.
2. A germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5 by weight of the soap of a synergistic germicidal mixture of from about 40% to about 10% by weight of said mixture of 3,4,5-tribromosalicylanilide and from about 60% to about 90% respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.
3. A germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.1% to about 0.5% by weight of the soap of a synergistic germicidal mixture of from about 35% to about 20% by weight of said mixture of 3,4,S-tribromosalicylanilide and from about 65 to about respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.
4. A germicidal soap bar consisting essentially of a water-soluble alkali metal soap having from about 8 to about 26 carbon atoms and from about 0.3% to about 0.5 by weight of the soap of a synergistic germicidal mixture of from about 35% to about 20% by weight of said mixture of 3,4,S-tribromosalicylanilide and from about 65% to about 80% respectively by weight of said mixture of 3,4,4-trichlorocarbanilide; said soap bar being substantially as white as the same soap bar without said synergistic mixture therein.
References Cited by the Examiner UNITED STATES PATENTS 3,057,920 10/1962 Schramm 252106 X 3,064,048 11/1962 Schramm 252-106 X FOREIGN PATENTS 106,388 2/1957 Argentina.
SAMUEL H. BLECH, Primary Examiner. ALBERT T. MEYERS, Examiner.
LEON D. ROSDOL, Assistant Examiner.

Claims (1)

1. A GERMICIDAL SOAP COMPOSITION CONSISTING ESSENTIALLY OF A WATER-SOLUBLE ALKALI METAL SOAP HAVING FROM ABOUT 8 TO ABOUT 26 CARBON ATOMS AND FROM ABOUT 0.1% TO ABOUT 0.5% BY WEIGHT OF THE SOAP OF A SYNERGISTIC GERMICIDAL MIXTURE OF FROM ABOUT 40% TO ABOUT 10% BY WEIGHT OF THE MIXTURE OF 3,4'',5-TRIBROMOSALICYLANILIDE AND FROM ABOUT 60% TO ABOUT 99% RESPECTIVELY BY WEIGHT OF 3,4,4''-TRICHLOROCARBANILIDEM; SAID COMPOSITION BEING SUBSTANTIALLY AS WHITE AS THE SAME COMPOSITION WITHOUT SAID SYNERGISTIC MIXTURE THEREIN.
US471475A 1960-06-27 1965-07-12 Germicidal soaps Expired - Lifetime US3284363A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US471475A US3284363A (en) 1960-06-27 1965-07-12 Germicidal soaps

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3875160A 1960-06-27 1960-06-27
US471475A US3284363A (en) 1960-06-27 1965-07-12 Germicidal soaps

Publications (1)

Publication Number Publication Date
US3284363A true US3284363A (en) 1966-11-08

Family

ID=26715508

Family Applications (1)

Application Number Title Priority Date Filing Date
US471475A Expired - Lifetime US3284363A (en) 1960-06-27 1965-07-12 Germicidal soaps

Country Status (1)

Country Link
US (1) US3284363A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3534121A (en) * 1966-05-24 1970-10-13 Advance Prod Gmbh Organotin composition and resins stabilized therewith
US3856952A (en) * 1973-03-01 1974-12-24 Pennwalt Corp Synergistic antimicrobial compositions employing certain n-(phenyl-carbamyl)amino-benzene sulfonyl flourides
US3989827A (en) * 1965-10-22 1976-11-02 Colgate-Palmolive Company Antibacterial composition
US4547307A (en) * 1981-09-17 1985-10-15 Udo Hoppe Cake of soap with deodorizing action
US5403506A (en) * 1993-09-30 1995-04-04 Church & Dwight Co., Inc. Deodorant detergent composition
US5417869A (en) * 1989-11-27 1995-05-23 Mobil Oil Corporation Surfactants and cutting oil formulations using these surfactants which resist microbial degradation
US5573699A (en) * 1993-09-30 1996-11-12 Church & Dwight Co., Inc. Deodorant soap or detergent composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057920A (en) * 1957-12-05 1962-10-09 Lever Brothers Ltd Process for preparing 3, 4', 5-tribromosalicylanilide in acetic acid
US3064048A (en) * 1958-07-10 1962-11-13 Lever Brothers Ltd Process for preparing 3, 4', 5-tribromosalicylanilide in the presence of a wetting agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057920A (en) * 1957-12-05 1962-10-09 Lever Brothers Ltd Process for preparing 3, 4', 5-tribromosalicylanilide in acetic acid
US3064048A (en) * 1958-07-10 1962-11-13 Lever Brothers Ltd Process for preparing 3, 4', 5-tribromosalicylanilide in the presence of a wetting agent

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989827A (en) * 1965-10-22 1976-11-02 Colgate-Palmolive Company Antibacterial composition
US3534121A (en) * 1966-05-24 1970-10-13 Advance Prod Gmbh Organotin composition and resins stabilized therewith
US3856952A (en) * 1973-03-01 1974-12-24 Pennwalt Corp Synergistic antimicrobial compositions employing certain n-(phenyl-carbamyl)amino-benzene sulfonyl flourides
US4547307A (en) * 1981-09-17 1985-10-15 Udo Hoppe Cake of soap with deodorizing action
US5417869A (en) * 1989-11-27 1995-05-23 Mobil Oil Corporation Surfactants and cutting oil formulations using these surfactants which resist microbial degradation
US5403506A (en) * 1993-09-30 1995-04-04 Church & Dwight Co., Inc. Deodorant detergent composition
US5573699A (en) * 1993-09-30 1996-11-12 Church & Dwight Co., Inc. Deodorant soap or detergent composition

Similar Documents

Publication Publication Date Title
US3296145A (en) Quaternary ammonium-tertiary amine oxide compositions
US5073382A (en) Divalent silver alkaline bactericide compositions
US3870647A (en) Liquid cleaning agent
US4468338A (en) Transparent soap composition
DE2161768A1 (en) Builder mixtures
US2353735A (en) Germicidal soap
US3284363A (en) Germicidal soaps
DE1158216B (en) Bactericidal agent
US3445398A (en) Synergistic antibacterial compositions
US5006529A (en) Soap compositions of enhanced antimicrobial effectiveness
AU680536B2 (en) Disinfectant-detergent composition
US4954281A (en) Soap compositions of enhanced antimicrobial effectiveness
US5874392A (en) Soap
CN113201416B (en) Alkaline multifunctional cleaning agent, preparation method and application thereof
US4746451A (en) Self-decontaminating cleansing preparations
CN109288727A (en) A kind of frosted type hand cleanser and preparation method thereof for industrial duplicate removal greasy dirt
US2792347A (en) Fatty acid mixtures and soaps derived therefrom
US5403506A (en) Deodorant detergent composition
US2353724A (en) Germicidal soap
US2937147A (en) Stabilized germicidal soaps and process of making the same
KR101926401B1 (en) Solid laundry soap composition for baby clothes or undergarment
US2864768A (en) Germicidally active soap containing reaction product of silver salt and ethyenethiourea
CN104862131A (en) Fruit and vegetable tableware detergent based on marine fish oil and preparation method thereof
JPS61188496A (en) Detergent composition
US3262884A (en) Skin cleaning composition