EP0729345A1

EP0729345A1 - Deodorising combination of agents based on alpha-omega alkane dicarboxylic acids and fatty acid partial glycerides

Info

Publication number: EP0729345A1
Application number: EP95900064A
Authority: EP
Inventors: Manfred Klier; Bernd Traupe; Florian Wolf; Manfred Roeckl
Original assignee: Beiersdorf AG
Current assignee: Beiersdorf AG
Priority date: 1993-11-20
Filing date: 1994-11-05
Publication date: 1996-09-04
Also published as: WO1995014458A1; DE4339605A1; JPH09505311A; US5780019A

Abstract

Cosmetic deodorants containing mixtures of I) α, Φ alkane dicarboxylic acids and II) fatty acid partial glycerides of unbranched fatty acids.

Description

description

Deodorant active ingredient combinations based on alpha-omega-alkanedicarboxylic acids and fatty acid partial glycerides

The present invention relates to cosmetic active ingredient combinations, in particular active ingredient combinations as an effective principle in cosmetic deodorants.

Cosmetic deodorants serve to eliminate body odor which arises when the fresh, odorless sweat is decomposed by microorganisms. The usual cosmetic deodorants are based on different active principles.

In so-called antiperspirants, astringents - primarily aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate) - can prevent the formation of sweat. Apart from the denaturation of the skin proteins, the substances used for this, depending on their dosage, have a drastic effect on the heat balance of the armpit region and should only be used in exceptional cases.

The use of antimicrobial substances in cosmetic deodorants can reduce the bacterial flora on the skin. In the ideal case, only the odor-causing microorganisms should be effectively reduced. In the

REPLACEMENT LEAF Practice has shown, however, that the entire micro flora of the skin can be impaired.

The sweat flow itself is not affected by this, in the ideal case only the microbial decomposition of the sweat is temporarily stopped.

The combination of astringents with anti ikrobiel 1 active substances in one and the same composition is also common. However, the disadvantages of both classes of active ingredient cannot be completely eliminated in this way.

Finally, body odor can also be covered by fragrances, a method that least meets the aesthetic needs of the consumer, since the mixture of body odor and perfume smells rather unpleasant.

However, most cosmetic deodorants, like most cosmetics as a whole, are perfumed even if they contain deodorizing agents. Perfuming can also serve to increase the consumer acceptance of a cosmetic product or to give a product a certain flair.

Perfuming cosmetic preparations containing active ingredients, in particular cosmetic deodorants, is not infrequently problematic because active ingredients and perfume components can occasionally react with one another and render them ineffective.

Deodorants should meet the following conditions:

1) They should cause reliable deodorization. 2) The natural biological processes of the skin must not be impaired by the deodorants.

3) The deodorants must be harmless in the event of overdosage or other improper use.

4) They should not accumulate on the skin after repeated use.

4) They should be easy to incorporate into conventional cosmetic formulations.

Both liquid deodorants, for example aerosol sprays, roll-ons and the like, and solid preparations, for example deodorant sticks ("sticks"), powder, powder sprays, intimate cleansing agents, etc., are known and customary.

The object of the present invention was therefore to develop cosmetic deodorants which do not have the disadvantages of the prior art. In particular, the deodorants should largely protect the microflora of the skin, but selectively reduce the number of microorganisms which are responsible for body odor.

Furthermore, it was an object of the invention to develop cosmetic deodorants which are notable for good skin tolerance. Under no circumstances should the deodorizing principles of action accumulate on the skin.

A further task was to develop cosmetic deodorants which harmonize with the largest possible number of customary cosmetic auxiliaries and additives, in particular those which are deodorising or antiperspirant. formulations of significant perfume ingredients with a pirating effect.

A further object of the invention was to provide cosmetic deodorants which are effective over a longer period of time, on the order of at least half a day, without their action noticeably diminishing.

Finally, it was an object of the present invention to develop deodorant cosmetic principles which can be incorporated as universally as possible into the most varied forms of administration of cosmetic deodorants without being limited to one or a few special forms of administration.

Surprisingly, it has been found, and this is the solution to all of these problems, namely cosmetic deodorants containing mixtures

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

remedy the disadvantages of the prior art.

European patent application EP-0 036 134 describes deodorising compositions, characterized by a content of derivatives of medium- to long-chain alkanoic acids, which also include the α, Ω-alkanedicarboxylic acids of the general formula

0

C- (CH ~) -C include

/ '2'n \

H-0 0-H with n = 4 to 10, but there is no reference to the teaching presented here in this document.

Furthermore, the German Offenlegungsschrift DE-OS 27 03 642 describes deodorising agents for personal hygiene, which include, among other things, certain α, Ω-alkanedicarboxylic acids, but there is no reference to the teaching presented here in this document either.

According to the invention, the α, Ω-alkanedicarboxylic acids are preferably selected from the group of substances which are of the generic formula

be written

where n can take numbers from 1 to 8.

n = 1 malonic acid n = 2 succinic acid n = 3 glutaric acid n = 4 adipic acid n = 5 pimelic acid n = 6 suberic acid n = 7 azelaic acid n ₌ 8 sebacic acid

Partial glycerides for the purposes of the present invention

(1) Diglycerol monocarboxylic acid ester

(2) Triglycerol monocarboxylic acid ester According to the invention, the di- or triglycerol units of the partial glycerides according to the invention are present as linear, unbranched molecules, ie "monoglycerol molecules" etherified via the respective OH groups in the 1- or 3-position.

3 2 1 H ₂ C-CH-CH ₂ (glycerin = "monoglycerin") HO OH OH

A small proportion of cyclic di- or triglycerol units and glycerol molecules etherified via the OH groups in the 2-position can be tolerated. However, it is advantageous to keep such impurities as low as possible.

The partial glycerides according to the invention based on diglycerol are preferably monocarboxylic acid monoesters and are preferably characterized by the following structure:

H C1-C, H-CH2-0-CH2-C, H-CH2-0-C || -R '

HO OH OH 0

where R 'represents an unbranched alkyl radical of 5 to 17 carbon atoms.

The partial glycerides according to the invention based on the triglycerol are preferably monocarboxylic acid monoesters and are preferably characterized by the following structure:

H2Ct-C | H-CH2 "-0-CH2-CiH-CH2-O-CH. • CH-CH-,

1 ι

HO OH 0 OH OH

R "-C = 0

where R "represents an unbranched alkyl radical of 5 to 17 carbon atoms. The fatty acids or monocarboxylic acids on which these esters are based are the

Hexanoic acid (caproic acid) (R ¹ or R "=

^"C 5 ^H 11 ^{) j}

Heptanoic acid (enanthic acid) (R 'or R "= -C ₆ H ₁₃ ),

Octanoic acid (caprylic acid) (R 'or R "= -C ₇ H ₁₅ ),

Nonanoic acid (pelargonic acid) (R ¹ or R "= -C ₈ H ₁₇ ),

Decanoic acid (capric acid) (R 'or R "= -C ₈ H ₁₉ ),

Undecanoic acid (R 'or R "= -C _{1 Q} H ₂₁ ),

10-undecenoic acid (undecylenic acid) (R 'or R "=

^_C 10 ^H 19 ⁾ '

Dodecanoic acid (lauric acid) (R ¹ or R "= -C ₁₁ H ₂₃ ),

Tridecanoic acid (R ¹ or R "= -C ₁₂ H ₂₅ ),

Tetradecanoic acid (myristic acid) (R ¹ or R "= -C ₁₃ H ₂₇ ),

Pentadecanoic acid (R 'or R "= -C ₁₄ H _2g ),

Hexadecanoic acid (pal itic acid) (R ¹ or R "= ^_C 15 ^H 31 ⁾ '

Heptadecanoic acid (margaric acid) (R 'or R "=

^"C 16 ^H 33 ^ '

Octadecanoic acid (stearic acid) (R 'or R "=

~ ^C 17 ^H 35 ^{) '}

R 'and R "are particularly advantageously chosen from the group of unbranched alkyl radicals with odd C numbers, in particular with 9, 11 and 13 C atoms.

In general, the esters of diglycerol are preferred to those of triglycerol according to the invention.

Are very particularly cheap

Diglycerol monocaprinate (DMC) R '= 9

Triglycerol Monolaurate (TML) R "= 11

Diglycerin onolaurate (DML) R '= 11

Triglycerol Monomyristate (TMM) R "= 13.

Diglycerol monocaprinate (DMC) has proven to be the preferred partial glyceride according to the invention. Partial glycerides based on such monocarboxylic acid esters, which are obtainable by a process as described in DE-OS 38 18 293, are particularly advantageous.

According to an advantageous embodiment of the present invention, mixtures of one or more monocarboxylic acid esters of diglycerol with one or more monocarboxylic acid esters of triglycerol are used as partial glycerides of unbranched fatty acids.

According to a further advantageous embodiment of the present invention, one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol in combination with other active substances (substitute active substances) customary in cosmetics are used as partial glycerides of unbranched fatty acids, auxiliary substances , Blending and / or additives used.

The blends and / or replacement active ingredients are then advantageously present in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on the 100 parts by weight of the total amount resulting from the monocarboxylic acid ester or the monocarboxylic acid esters of diglycerol and / or triglycerol and these substitute active ingredients and / or blends.

It is beneficial to the content

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

to be chosen so that ratios of I) and II) such as 5: 1 to 1: 5, in particular such as 1: 1, very particularly advantageously such as 1: 3 arise. According to the invention, a method for combating human body odor caused by microbial decomposition of apocrine sweat is further characterized in that an effective amount of

Mixtures of

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

which may optionally be in a suitable cosmetic carrier, is applied to the skin.

Finally, the use of mixtures is also in accordance with the invention

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

which can optionally be present in a suitable cosmetic carrier, for controlling gram-positive, in particular coryneform bacteria, or the use of mixtures of

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

which may be present in a suitable cosmetic carrier, to prevent the growth of gram-positive, especially coryneform, bacteria.

The cosmetic deodorants according to the invention are particularly advantageously characterized in that the α, Ω-alkanedicarboxylic acids are present in concentrations of 0.05-10.00 % By weight, preferably 0.1-5.0% by weight, are present, in each case based on the total weight of the preparations.

The cosmetic deodorants according to the invention are also particularly advantageously characterized in that the fatty acid partial glycerides of unbranched fatty acids are present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0% by weight, based in each case on the Total weight of the preparations.

The cosmetic deodorants according to the invention can be in the form of aerosols, that is to say from aerosol containers, squeeze bottles or preparations which can be sprayed by a pump device, or in the form of liquid compositions which can be applied by means of roll-on devices, as deodorant sticks (deodorant sticks). Sticks) and in the form of W / 0 or O / W emulsions that can be applied from normal bottles and containers, e.g. Creams or lotions. Furthermore, the cosmetic deodorants can advantageously be in the form of deodorizing tinctures, deodorizing intimate cleansing agents, deodorizing shampoos, deodorising shower or bath preparations, deodorising powders or deodorising powder sprays.

In addition to water, ethanol and isopropanol, glycerol and propylene glycol, skin-caring fat or fat-like substances, such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-0ctyldodecanol, can be used as customary cosmetic carriers for the production of the deodorant preparations according to the invention in the quantitative amounts customary for such preparations ¬ ratios are used as well as slime-forming substances and thickeners, such as hydroxyethyl or hydroxypropyl cellulose, polyvinyl pyrrolidone, but also in small quantities cyclic silicone oils (polydimethylsiloxanes) and liquid polymethylphenylsiloxanes of low viscosity. Suitable blowing agents for cosmetic deodorants according to the invention which can be sprayed from aerosol containers are the customary, known volatile, liquefied blowing agents, for example hydrocarbons (propane, butane, isobutane), which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.

Of course, the person skilled in the art knows that there are non-toxic propellant gases per se which would in principle be suitable for the present invention, but which should nevertheless be dispensed with because of their unsafe effect on the environment or other associated circumstances, in particular chlorofluorocarbons (CFCs). .

As emulsifiers for the production of the cosmetic deodorants according to the invention, which should advantageously be applied as liquid preparations to the desired skin areas by means of a roll-on device, and which are present in the preparations in small amounts, for example 2 to 5 Ge wichts.- ⁰ ^, based on the total composition, can be used non-ionic types, such as polyoxyethylene fatty alcohol ethers, for example cetostearyl alcohol polyethylene glycol ethers with 12 or 20 added ethylene oxide units per molecule, cetostearyl alcohol and sorbitan esters and sorbitan esters -Ethylene oxide compounds (eg sorbitan monostearate and polyoxyethylene sorbitan onostearate) and long-chain, higher molecular weight waxy polyglycol ethers have been found to be suitable.

In addition to the constituents mentioned, the deodorant cosmetic preparations according to the invention can contain perfume, dyes, antioxidants (for example α-tocopherol and its derivatives or butylated hydroxytoluene (BHT = 2,6-di-tert-butyl-4-methylphenol) in amounts of 0 , 01 to 0.03%, based on the total composition), suspending agent, Buffer mixtures or other common cosmetic raw materials can be added.

It is advantageous to choose the pH of the preparations according to the invention in the acidic to neutral range. The pH of the preparations according to the invention is particularly advantageously selected in the range from 4.5 to 6.5, in particular around 5.5.

The amount of cosmetic carrier and perfume to be used in each case can easily be determined by a person skilled in the art depending on the type of product in question by simply trying it out.

Substances and perfume oils which are stable, do not irritate the skin and already have antibacterial or bacteriostatic properties as such are also suitable for perfuming.

Apart from special preparations, each of which is noted separately in the examples, the cosmetic preparations are produced in a customary manner, usually simply by mixing with stirring, if appropriate with gentle heating. It offers no difficulties. For emulsions fat phase and water phase e.g. prepared separately, optionally with heating and then emulsified.

Otherwise, the usual measures for compiling cosmetic formulations, which are familiar to the person skilled in the art, must be observed.

If the compositions according to the invention are to be incorporated into powder sprays, the suspension bases for this can advantageously be selected from the group Silica gels (e.g. those sold under the trade name

Aerosil are available), diatomaceous earth, talc, modified starch, titanium dioxide, silk powder, nylon powder, polyethylene powder and related substances.

Advantageous exemplary embodiments of the present invention follow. The numerical values given always relate to% by weight, unless expressly stated otherwise.

Examples 1-4

Pump sprays

a)

Ethanol 69.00 65.00 65.00 65.00

Propylene glycol 2.00 2.00 2.00 2.00

Ceteareth-25

("Cremophor ^R A25") 3.00 - - 2.00

PEG-40 hydrogenated

Castor oil - 2.50 2.25 -

Adipic acid 0.25 - - 0.50

Succinic acid - 0.30 0.40 -

DMC 0.50 0.50 - -

DML - - 0.70 0.60

Perfume q. s. q. s. q. s. q. s.

b)

H ₂ 0 demin. NaOH 10% ad pH 5.5 each ad 100.00

Manufacturing:

The components under a) are heated with stirring until the mixture is melted clear.

Mixture b) is prepared after the required amount of NaOH solution has been determined in order to obtain a pH of about 5.5 in the finished product. Examples 5-8

Roll-on gels 5 6 7 8

a)

1,3-butanediol 2.00 2.00 2.00 2.00 Dipropylene glycol 1.50 2.00 1.50 2.00 Hydroxyethylcellulose 0.40 0.40 0.40 0.40

b)

Ethanol 50.00 55.00 50.00 55.00

PEG-40 hydrogenated

Castor oil 2.00 2.00 1.50 1.50

Adipic acid 0.40 - 0.50 -

Azelaic acid 0.30-0.40

DMC 0.50 0.50 - -

TML - 0.90 0.80

Perfume q.s. q. s. q. s. q. s.

c)

H ₂ 0 demin.

NaOH 10% ad ph 5.5 each ad 100.00

Manufacturing:

The constituents mentioned under a) are dispersed. Mixture c) is prepared after preliminary determination of the required amount of NaOH solution in order to obtain a pH of about 5.5 in the finished product and added to a). The mixture is allowed to swell at room temperature, a solution of the below (b) mentioned components are added after about 15 minutes. The resulting mixture is homogenized and can be filled.

Examples 9-10

Roll-on emulsions 10

a)

P0E-21 stearyl ether

("Brij 721") 1, 50 1, 50

P0E-2 stearyl ether

("Brij 72") 2.50 2.50

P0P-15 stearyl ether

("Arlamol E") 3.50 3.00

Octyldodecanol 6.00 6.00

Methyl paraben 0.20

Adipic acid 0.50 0.40

DMC

b)

Ethanol 12.00 perfume q.s q.s

O

H ₂ 0 demin NaOH 10% ad ph 5.5 each ad 100.00 The mixture c) is prepared after the required amount of NaOH solution has been determined in order to obtain a pH of about 5.5 in the finished product.

The components mentioned under a) and c) are each heated to 75 ° C. with stirring. Components a) to c) are then added.

The mixture is cooled to 35 ° C. A solution is prepared from the components b), which is heated to 35 ° C. and added to the mixture of a) and c) with stirring.

Examples 11-12

Wax pencils 11 12

Trilaurin 37.50 37.50

Glyceryl stearate, self-emitting 10.00 1 0,. 00

Beeswax / replacement 24.00 24.00

Azelaic acid 0.60

Adipic acid 0: 70

DMC 1, 10 1. , 1 0

Perfume q.s. q. s.

Caprylic / Capric

Triglyceride - each ad 100.00 -

The ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.

Claims

claims

1. Cosmetic deodorants containing mixtures of

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids.

2. Cosmetic deodorants according to claim 1, characterized in that the fatty acid partial glycerides are selected from the group of

(1) Monocarboxylic acid monoesters of the diglycerol of the structures

H C-CH-CH -0-CH „-CH-CH -0-CR 2 ι i 2 2 _f 2 t |

HO OH OH

where R 'represents an unbranched alkyl radical of 5 to 17 carbon atoms,

(2) Monocarboxylic acid monoesters of the triglycerol of the structures

H2C | -C (H-CH2-0-CH2-C «H-CH2-0-CH2-C _\ HC, H2-

HO OH 0 OH OH

R "-C = 0

where R "represents an unbranched alkyl radical of 5 to 17 carbon atoms.

3. Cosmetic deodorants according to claim 1, by a content of

I) α, Ω-alkanedicarboxylic acids and

II) - Diglycerol monocaprinate (DMC) and / or

Triglycerol monolaurate (TML) and / or Diglycerol monolaurate (DML) and / or triglycerol monomyristate (TMM)

characterized.

4. Cosmetic deodorants according to claim 1, characterized in that the α, Ω-alkanedicarboxylic acids are selected from the group

Malonic acid, succinic acid, glutaric acid, adipic acid, pelic acid, suberic acid, azelaic acid, sebacic acid.

5. Cosmetic deodorants according to claim 1, characterized in that the α, Ω-alkanedicarboxylic acids are present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0% by weight, each based on the total weight of the preparations.

6. Cosmetic deodorants according to claim 1, characterized in that the fatty acid partial glycerides of unbranched fatty acids are present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0% by weight, in each case based on the total weight of the preparations.

7. Cosmetic deodorants according to claim 1, characterized in that they are buffered to a pH, selected from the range from 4.5 to 6.5.

8. Use of mixtures

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

as a deodorizing principle for cosmetic deodorants.

9. Use of mixtures

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

to control gram-positive, especially coryneform bacteria or to prevent their growth.

10. A method for controlling the human body odor caused by microbial decomposition of apocrine sweat, characterized in that an effective amount of mixtures consists of

I) α, Ω-alkanedicarboxylic acids and

II) Fatty acid partial glycerides of unbranched fatty acids

which may optionally be in a suitable cosmetic carrier, is applied to the skin.