CA1085299A - Lactic acid composition and method of use - Google Patents

Lactic acid composition and method of use

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Publication number
CA1085299A
CA1085299A CA272,066A CA272066A CA1085299A CA 1085299 A CA1085299 A CA 1085299A CA 272066 A CA272066 A CA 272066A CA 1085299 A CA1085299 A CA 1085299A
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Canada
Prior art keywords
lactic acid
solution
alcohol
yielding compound
mixtures
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
Application number
CA272,066A
Other languages
French (fr)
Inventor
Joseph D. Mandell
Sheldon L. Matlow
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Individual
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Individual
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Publication of CA1085299A publication Critical patent/CA1085299A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0014Skin, i.e. galenical aspects of topical compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Emergency Medicine (AREA)
  • Dentistry (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Abstract of the Disclosure A solution having biostatic activity and comprising a lactic acid yielding compound, an alcohol, and water and having a pH level no greater than about 3Ø
The solution can be used as a deodorant, as a treatment for acne, chapping, dandruff, "athlete's foot", or psoriasis, and as a combination cleanser and disinfectant.

Description

~35Z~9 Background of the Invention Liviny organisms, inc]uding microorganisms such as bacteria, require the bioloyical oxidation of carbohydrates as an eneryy source. During this succession of oxidation reactions, ylycoyen, the form in which carbohydrates are stored in an animal body, is converted to carbon dioxide and water. This conversion may be divided into three stayes, (a) ylycogen is broken down into . :

its component D-ylucose molecules; ~b) in glycolysis, D-glucose is itself broken down into three carbon compounds;

and (c) such compounds, in respiration, are converted into carbon dioxide and water.
The last step of-glycolysis is the reduction of - ~;

pyruvic acid to lactic acid accordiny to the followiny equation:

CH3COCOO + NADH + ~ = CH3CHOHCOO ~ NAD~ (1~ i.

Pyruvate Reduced Lactate Nicotinamide ~ :
nicotinamide adenine adenine dinucleotide dinucleotide The above reaction is catalyzed by a set of enzymes ~ collectively referred to as "lactate dehydroyenase".
:. This reaction is i~portant for the regeneration of ~AD which is required for the conversion of 3-phosphoylycer-aldehyde to 1,3~diphosphoglycerate in the Embden-
2~ ~eyerhof-Parnas (EMP) pathway, for the conversion of pyruvate to acetyl.-coenzyme A, called "acetyl CoA", and for the conversion of isocitrate to oxalosuccinate t 2-ke~toglutarate ; to succinyl-coenzyme A, and mala~.e to oxaloacetate in the tricarboxylic acid cycle (aerobic oxidation of ylucose)O
3~ One known technique for limitiny the growth of ' :

: -2-1~52~S~
' harmful bacteria or other microorganisms is by the addition of an inhibitor of an enzyme such as an antibiotic. One problem wlth this approach is that if the bacteria are not destroyed rapidly, a mutant population may arise which is not affected by the inhibitor. For example, there are now several strains of staphylococcus which are resistant to the antibiotic penieillin. Another problem with this approach is the serious allergic reaction of certain patients to the presence of such foreign antibiotic substances.
It is known that the growth of microorganisms can be reduced by lowering the pH level of their environment.
~or example, microorganisms ~row substantially slower or are killed at a pH of 3 in comparison to a pH of 4. One reason for this is that a low pH environment is deleterious to cytochrome C which is necessary for the oxidative phosphorylation path.
Mieroorganisms such as baeteria are also adversely effected by contact with aleohols which serve to denature the protein of the microorganisms. Thus, alcohol ; is a well known bactericide.
It is also known that the unpleasant odor due to perspiration is caused by the attack of bacteria on the secretions of the sweat glands. U.S. patent 3,124,506 discloses a number of eompositions which are-stated to be useful as an inhibitor of foot odor or as an underarm deodorant. There is no disclosure of any sug~ested meehanism for the effeetiveness of such eompositions for this purpose. ~lowever, one set of nonaqueous compositlons including malie aeid,he~achlorophenef and isopropyl ~3S299 alcohol, is disclosed for use as a deodorant. Another set of compositions is disclosed for use as a dentifrice and prophylactic nose and throat composition including a water based mixture of calcium lactate, malic acid, or lactic acid and calcium malate, both in water. There is no suggestion of using an alcohol composition in this formulation or that the composition could exclude calcium.
- Summary of the Invention and Objects ~ -In accordance with the present invention, a solution has been provided having excellent biostatic activity for use as a deodorant, to treat acne, chapping, dandruff, "athlete's foot", or psoriasis, and as a cleanser ar~
disinfectant. A biostat or biostatic material is defined as a chemical composition which inhibits the growth of i~
liying cells such as microorganisms (e.g~, bacteria).
The composition includes effective quantities of a lactic acid yielding compound (e~g., lactic acid), an alcohol, and water, and has a pH level no greater than about 3Ø
The biostatic ac~ivity of thessol~tion derives from three primary factors. Firstly, the presence of lactic acid thermodynamically drives the reversible reaction of equation (1) to the left to reduce the concentration of NAD . As set forth above, NAD is essential in the 2~ production of energy in microorganisms. Secondly, since the solution includes no metal ion, it is not buffered and so has a highly acidic pH level which is detrimental to the function of cytochrome Cl a~so important in energy production oflmicroorganisms. Thirdly, the presence of the alcohol denatures; the protein oi the microorganisms.
-4-~S2~
- . .
When the solution is emplo~ed as a disinfectant and cleanser, in addition to the above biostatic activity, the lactic acid reacts with soap to displace the sodium ion of typical soap films to form long chain fatty acids which S are soluble in the alcoholic solution. Thus, difficult to remove soap deposits are readily washed awa~ in the alcoholic solution without large expenditures of effort.
It is an object of the present invention to provide a solution having excellent biostatic activity in ;
- 10 comparison to the prior art.
It is a further object of the invention to provide such a solution which does not cause an allergic - reaction.
It is another object of the invention to,provide a solution with activity unaffected by potential growth of mutant microorganism populations. ;~
It is a further object of the invention to provide `
a solution effective as a deodorant and bactericide.
- It is a further object of the invention to provide a solution effective for the treatment of "athlete's oot".
It is a further object~of the invention to provide ~; such a solutioh capa~le of treating skin disorders such as chapped skin, dandruff, and psoriasis.
It is an additional object of the invention to provide such a solution which functions as an effective cleanser and disinfectant.
Further objects and features of the invention will be apparen~ from the following description of the preferred e~bodiments.
~' .
, .. . . ..... I .. . . :

352~

Detailed Description of the Preferred Embodiments The biostatic solution of the present invention includes a lac~ic acid yielding compound, a volatile alcohol, and water. The term "lactic acid yielding coMpound"
is defined to include lactic acid, compounds hydrolyzable to lactic acid and mixtures of the same. Substances hydrolyzable to lactic acid include lactide, lactyl lactic acid, and higher polymers, ethyl and methyl lactate, and mixtures of the same. For simplicity of description, the specification will refer to lactic acid as the lactic acid yielding compound.
For convenience of reference, equation (1) set forth above is repeated as f~llows:
CH3COCOO + NADH + ~ CH3CHOHCOO + NAD (1) Pyruvate Reduced Lactate Nicotinamide nicotinamide adenine adenine dinucleotide dinucleotide By well known principles of chemical equilibria, it is -- 20 apparent that an increase in lactate ion or its source, lactic acid, in the above ~uation will drive the reaction to the left~ and so reduce the production of NAD . As set foi-th above, th~is reduces the energy source for the yrowth of microorganisms.
It has been determined that the lactic acid concentration in perspiration varies from 0.147 to 0.371 weight/vol~ne percent with a mean value of 0.232 percent (Ralph G. Harry, The Principles and Practice of Modern Cosmetics, Vol. 1, Chemical Publishing Co., New York, 3Q (1962), p. 469). For the present formulation to be effective as a deodorant in the presence of perspiration, ,~ .
, , .
:, :

10~3SZ~

the additional lactic acid concentratio~ should be substan~ial in comparison to that present in the ~erspiration. A suitable lower value for this purpose of about 0.5 weight/volume percent of lactic acid will be effective for use as a deodorant for a typical human application.
In view of the foregoing, a suitable ranye of lactic acid in the composition is from about 0.5% to 2 to 4% or more. The maximum value is determined as that which would cause undue irritation in the particular area of the subject treated. Of course, this limitation is not present when the solution is employed as a combination cleanser and disinfectant as set forth hereinafter.
The foregoing lower limitation of 0.5% is related -to the destruction of bacteria which co~bines with perspiration to yield an unpleasant odor. It should be understood that other living cells such as fungi and yeast are also inhibited by the same reduction in the source of energy. It is assumed that the foregoing lower limit would be comparable to that which would be effective in the reduction of such other living cell growths on ~ .
the skin. ' Lactic acid also serves to lower the pH of the solution to a level between about 2.0 and 3.0 which ; 25 inhibits the function of cytochrome C, which also reduces the energy source for growth of microorganisms as set forth aboveO It is preferable to maintain the pH of the solution at a level below about 3.0 to take advantage of this effect. Thus, it is preferable that the solution exclude any substantial amount of metal ion compound which ~3525~

:
would have a buffering efect in combination with the acid.
It is noted that most soaps are alkaline and so increase the pH of the skin to levels on the order of 8 to ~. At such pH levels, the skin is highly susceptible to bacteria growth before it returns to its normal acidic levels. This is a particular problem with unhealthy skin which takes a longer time to return to its normal pH levels. This problem is avoided by the use of the present solution which actually lowers the pH level of the skin to inhibit growth of bacteria or the like.
The second element in the present composition is ` a- alcohol which is known to be an effective bactericide by denaturation of the protein content of bacteria or the like. In addition, it has a relatively low surface tension enabling it to penetrate deeply into crevices in ~ ~ -the surface of the skin and into the pores. Furthermore, by attacking the lipoproteins in the microorganism~i cell membranes, the alcohol permits more effective penetration oi the solution into the cells. Another function of the alcohol is dependent on its high volatility. Thus, when it is present in a high proportion, the mixture vaporizes rapidly, an important feature for use as a deodorant or the like.
Suitable alcohols which may be employed ln the above compositions are the lower alkyl alcohols such as - methyl, ethyl, n-propyl, and isopropyl alcohol. It is known that higher alcohols have better bactericidal efficiency but lower solubility in water, lower volatility, and a higher cost. Isopropyl alcoh~ol is a pre~erable :. .

~ - -8-.

3S~9 balance for all of these factors.
The concentrat;on of the alcohol is selected to be at least a minimum quantity for good efficacy o~ biostatic activity as well as causing at least a minimum rate of evaporation of solution after application. For application to a human subject, the maximum concentration is determined by an acceptable level of irritation to tlle particular area of contact with the skin. Suitable concentrations of isopropyl alcohol may range between ' 30 and 90~ (volume/volume) while an optimum concentration is on the order of 50%.
The remain,der of the solution comprises water which serves as a diluent for adjustment of the desired --concentrations. Thus, the bulk of the remainder of the solution after addition of alcohol and lactic acid comprises ~ater. The water also serves as a medium for '~ ' ' ionizing the lactic acid for reduction of the pH level -, of the solutionO
The mechanism for dermatological application as a deodorant as for underarm or foot odors is for the solution to attac'k the',bacteria in the vicinity of the secretions of the sweat glands. Since such bacteria cause the unpleasar.t odors in such secretions, the present solution is particularly effective as a deodorant. When used as a deodorant, a maximum alcohol content should be employed,as this increases the rate of evaporation.
The present solution may also serve as a bactericicle ,~
in treatment of acne. It is known that coryne bacterium_ ', acnes and other bacteriaisecrete lipases which hydrolyze .
fats in the sebum,~ producing long chain fatt~ acids which _g_ 2~9 . .

are irritating to the f~llicles. The present solution serves to prevent the follicular inflammation by inhibiting the growth of the lipase secreting bacteria.
Chapped skin, dandruff and psoriasis are all abnormal skin conditions which may be aggravated by -secondary microbial infections. It has been found that the present solution is an effective treatment for such abnormal skin conditions. The present solution can also be employed in the treatment of fungus infections such as "athlete's foot" and yeast infections.
The present solution is also effective as a -~
- post-scrub lotion, especially for persons re~uired to wash their hands frequently such as medical doctors.
The present solution leaves the skin moist after ;
application and at a pH level which minimizes bacterial growth. -~
In addition,to;the foregoing use as a treatment for human subjects, the solution of the present invention ; is also particularly effective for simultaneous cleaning and disinfecting of a dirty surface. It has been found that application of the solution removes dirt, especially in the form of dirty soap films with minimal effort while simultaneously disinfecting the surface. The ease of removal of the dirt such as soap is believed to be due to the following mechanism. The soap, formed of a metal (e.g., calcium) salt of a fatty acid, reacts with the lactic acid component of the solution to form a fatty acid which is highly soluble in the alcoholic solution. Such fatty acid is dissolved in the alcohol ~ -and rapidly removed from the surface without the necessity :
~, , ;
, , , ; . ~

352~9 for excesslve rubbing.
It should be apparent that other additives may be added in minor proportion to augment the above solutions.
~or example, scents may be added to form an after shave lotion or scented deodorant. Also, humec-tants such as glycerine or propylene glycol may be added to a solution, or mineral oil may be used to increase lubricity for such use as a hand lotion. Furthermore, malonic acid may be added to the deodorants to reduce the amount ; 10 of perspiration. Finally, urea may be employed to assist in the inhibition of yeast cell growth.
For convenience, the solution of the present invention may be prepared ~y the consumer at home from its components. Thus, a lactic acid ~orming compound in solid form such as a tablet or powder:may-be ~dt~ed to a commercially available aqueous alcoholic solution (e.g., isopropyl alcohol). Lactide is a suitable lactic acid yielding solid~ The solution of the present invention may also be prepared by the consumer by adding a commercially 2Q available a~ueous alcoholic solution to an aqueous solution of a lactic acid ,forming compound.
A further disclosure of the nature of the present invention is provided by the following specific examples ;~
of the practice of the invention. It should be understood that the data disclosed serve only as examples and are not intended to limit the scope of the invention. The following examples will utilize a three-digit number as a code for the formulations. The first digit refers to the lactic acid concentration in weight/volume percent. The second and third digits refer to the percentage of isopropyl alcohol (volume/volume). The remainder of the formulation is water.
~' ; ~, !
5~9 xample 1 Formula 230 is a satisEactory underarm deodorant, but has a xelatively low evaporation rate. Formula 260 is preferred for this purpose as having a rapid evaporation rate without being unduly irritating. Yormula 460 is employed for persons with severe body odor problems. The ~`
same formulations may be employed as a foot deodorant or treatment for "athlete's foot" or other fungus ; infections.
Example 2 .~ :.
Formulation 260 is employed for the treatmellc of .: , acne. If a person has a relatively non-sensitive .
skin, the stronger for-.ulation, 460, is preferable. For ; very difficult cases of acne, formulations 480, or 660 are employed.
Exam~le 3 Formulation 230 is employed as a treatment for aandruff effectively since residual moisture in the hair is not detrimental. Formulations 260 or 460 are employed for more severe cases of dandruff.
.
Example 4 Formulations 260 and 460 are employed for the treatment of chapped skin. If formulation 460 is too `;
irritating for severe cases, alternating use of formulations 260 and 460 are effective.
~ . :
.. . .

';
.

.' ' , . . .

Claims (12)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A solution having biostatic activity comprising a lactic acid yielding compound, a lower alkyl alcohol, and water, said biostatic solution having a pH level no greater than about 3.0 and wherein said alcohol comprises 30 to 90% by volume of the total solution and said lactic acid yielding compound comprises at least 0.5% of said solution on a weight/volume basis.
2. The solution of Claim 1 in which said volatile alcohol is selected from the group consisting of methyl alcohol, ethyl alcohol, n-propyl alcohol, and isopropyl alcohol.
3. The solution of Claim 1 in which said lactic acid yielding compound is selected from the group consisting of lactic acid, compounds hydrolyzable to lactic acid, and mixtures thereof.
4. The solution of Claim 3 in which said hydrolyzable compounds are selected from the group consisting of lactide, lactyl lactic acid, and higher polymers, ethyl lactate, methyl lactate, and mixtures thereof.
5. The solution of Claim 3 in which said lactic acid yielding com-pound comprises lactic acid.
6. The solution of Claim 1 essentially devoid of metal ion.
7. The solution of Claim 2 in which said lactic acid yielding compound is selected from the group consisting of lactic acid, compounds hydrolyzable to lactic acid, and mixtures thereof.
8. The solution of Claim 7 in which said hydrolzable compounds are selected from the group consisting of lactide, lactyl lactic acid, and higher polymers, ethyl lactate, methyl lactate, and mixtures thereof.
9. The solution of Claim 7 in which said lactic acid yielding compound comprises lactic acid.
10. A method for cleaning and disinfecting a dirty surface comprising applying to the surface a solution comprising a lactic acid yielding compound, a lower alkyl alcohol, and water, said solution. having a pH level no greater than about 3.0 and wherein said alcohol comprises 30 to 90% by volume of the total solution and said lactic acid yielding compound comprises at least 0.5% of said solution on a weight/volume basis.
11. The method of Claim 10 in which said surface is coated with a soap in which the lactic acid from said lactic acid yielding compound reacts with said soap to yield a fatty acid soluble in alcohol which is dissolved in said alcohol and removed from said surface.
12. The method of Claim 10 in which said lactic acid yielding compound comprises lactic acid, lactide, lactyl lactic acid, and higher polymers, ethyl lactate, methyl lactate and mixtures thereof.
CA272,066A 1976-03-05 1977-02-18 Lactic acid composition and method of use Expired CA1085299A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66410276A 1976-03-05 1976-03-05
US664,102 1976-03-05

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CA1085299A true CA1085299A (en) 1980-09-09

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CA (1) CA1085299A (en)
DE (1) DE2709267A1 (en)
FR (1) FR2342725A1 (en)
GB (1) GB1561475A (en)
IL (1) IL51559A0 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9566223B2 (en) * 2010-04-17 2017-02-14 Shannon Elizabeth Klingman Antiperspirants and deodorants

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1555796A (en) * 1976-10-15 1979-11-14 Unilever Ltd Composition for treating acne
FR2414332A1 (en) * 1978-01-13 1979-08-10 Unilever Nv DEODORIZING ITEMS TO DISCARD AFTER USE
GB2013493C (en) * 1978-01-13 1996-02-20 Unilever Ltd Skin treatment product
JPS5758876A (en) * 1980-09-26 1982-04-08 Ueno Seiyaku Kk Germicide for food, raw ingredient of food, and device for processing food, and its use
PH18373A (en) * 1982-02-02 1985-06-13 Unilever Nv Skin treatment composition
US5059241A (en) * 1983-07-06 1991-10-22 Union Oil Company Of California Plant growth regulation
US4863506A (en) * 1983-07-06 1989-09-05 Union Oil Company Of California Methods for regulating the growth of plants and growth regulant compositions
AU560740B2 (en) * 1984-01-09 1987-04-16 Unilever Plc Pharmaceutical emulsion comprising an organic lactate and silicone oil
FR2572652B1 (en) * 1984-11-05 1987-01-16 Meyer Jean PHARMACEUTICAL COMPOSITION FOR ANTISEPTIC USE
FI861589A (en) * 1986-04-14 1987-10-16 Union Oil Company Of California FOERFARANDE FOER REGLERING AV TILLVAEXTEN AV VAEXTER OCH TILLVAEXTREGLERANDE KOMPOSITIONER.
AU668559B2 (en) * 1992-06-03 1996-05-09 Unilever Plc Improvements relating to cosmetic compositions
DE19543695A1 (en) * 1995-11-23 1997-05-28 Beiersdorf Ag Compositions based on alpha-hydroxyalkanoic acids and squalene, effective against bacteria, Mycota and viruses
DE10154368A1 (en) * 2001-11-06 2003-05-15 Henkel Kgaa Beta-glucuronidase inhibitors in deodorants and antiperspirants
US8790671B2 (en) 2007-04-20 2014-07-29 Bioequal Ag Topical fungicidal agents for treating nail disorders
DE102018207702A1 (en) * 2018-05-17 2019-11-21 Beiersdorf Ag Process for sweat reduction with malonic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9566223B2 (en) * 2010-04-17 2017-02-14 Shannon Elizabeth Klingman Antiperspirants and deodorants

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FR2342725B1 (en) 1980-03-14
IL51559A0 (en) 1977-04-29
GB1561475A (en) 1980-02-20
FR2342725A1 (en) 1977-09-30
DE2709267A1 (en) 1977-09-15

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