WO1998023253A1

WO1998023253A1 - Use of 3-(n-butylacetamino) propionic acid ethyl ester

Info

Publication number: WO1998023253A1
Application number: PCT/EP1997/006384
Authority: WO
Inventors: Kurz Thekla; Sabine Hitzel; Dorothee Wille; Mohammad Jalalian
Original assignee: Merck Patent Gmbh
Priority date: 1996-11-26
Filing date: 1997-11-15
Publication date: 1998-06-04
Also published as: DE19648819A1

Abstract

The invention relates to the use of 3-(N-butylacetamino) propionic acid ethyl ester for improving the solubility of sunscreens and cosmetic preparations containing sunscreens, in which 3-(N-butylacetamino) propionic acid ethyl ester is used to improve the solubility of these sunscreens.

Description

Use of 3- (N-butylacetamino) propionic acid ethyl ester

The invention relates to the use of 3- (N-butylacetamino) propionic acid ethyl ester to improve the solubility of light protection filters.

As is known, the skin is sensitive to the sun's rays, which can cause normal sunburn or erythema, but also more or less pronounced burns.

However, sun rays also have other negative effects: they cause the skin to lose its elasticity and wrinkles and thus lead to premature aging. Sometimes you can also observe dermatoses. In extreme cases, it happens to some people

Occurrence of skin cancer.

It is also desirable to protect hair against photochemical damage in order to prevent changes in color shades, discoloration or mechanical damage.

It is known that many light protection filters have only a very low solubility in cosmetic preparations. This gives rise to problems in incorporating the amounts of light protection filter which are in principle necessary for real protection against sun rays into the corresponding formulations.

As is known, the most dangerous part of the sun's rays is formed by the ultraviolet rays with a wavelength of less than 400 nm. It is also known that due to the presence of the ozone layer in the earth's atmosphere, which absorbs part of the sun's radiation, the lower limit of the ultraviolet rays that reach the earth's surface is approximately 280 nm.

It therefore appears desirable to use preparations with improved filter potential, ie with an increased concentration of known and proven ones To provide light protection filters, which can absorb UV rays in a wavelength range from 280 to 400 nm, ie both UVB rays with a wavelength between 280 and 320 nm, which play a decisive role in the formation of a sun erythema, as well as UVA - Rays with a wavelength between 320 and 400 nm, which brown the skin but also age it, favor the triggering of an erythematous reaction or enlarge this reaction in certain people or even trigger phototoxic or photoallergic reactions

The sun protection filters commonly used in cosmetics today are divided into UVA and UVB filters. There are many substances known and preserved from the specialist literature for both UV ranges, for example here are only substances such as Eusolex ® 6300 or Eusolex® 232, dibenzoyl methanes such as Eusolex® 9020 or Eusolex® 8020, Benzophenone or Octyl Triazone (Uvinul® T 150)

However, it is also known that the light protection filters generally have only a relatively low percentage in the oils used in cosmetics, and therefore their filter potential cannot be fully exploited

Surprisingly, it has now been found that ethyl 3- (N-butylacetamιno) propionate has a particularly high bulk capacity for light protection filters, which leads to cosmetic preparations which have a significantly higher UV filter content and thus a significantly improved content

Have protection against sun rays

The substance 3- (N-butylacetamιno) propionic acid ethyl ester is known to have an insect repellent effect, and is thus incorporated into cosmetic formulations used to repel insects

3- (N-Butylacetamιno) -propιonsaureethylester is usually incorporated in concentrations up to 30% in cosmetic formulations. It is a very polar oil that is due to its mixed availability of water and oils differs from traditional cosmetic oils.

This substance also has the great advantage of not showing any toxic or allergic reactions to the skin.

The formulations according to the invention have a high sun protection factor and thus a long-lasting protective effect.

Furthermore, the formulations according to the invention can also be used for the preventive treatment of inflammation and allergies to the skin, for the prevention of certain types of cancer and also partly for repelling insects.

They are evenly distributed in the conventional cosmetic carriers and can form a continuous film, especially in fat carriers; they can be applied to the skin in this way to form an effective protective film.

The invention thus relates to the use of ethyl 3- (N-butylacetamino) propionate to improve the solubility of light protection filters.

The invention also relates to a cosmetic preparation containing light protection filters, which is characterized in that ethyl 3- (N-butylacetamino) propionate is used to improve the solubility of these light protection filters.

The content of ethyl 3- (N-butylacetamino) propionate in the formulations according to the invention can be up to 90% by weight, preferably the content is between 1 and 50%, a content of 10 to 35% by weight is particularly preferred.

As already mentioned, the substance 3- (N-butylacetamino) propionic acid ethyl ester is known as an insect repellent. The insect repellent can

Trade can be obtained, for example from Merck KGaA, Darmstadt. It shows such excellent properties as a very good skin and mucous membrane tolerance without toxic, allergic or sensitizing properties and no skin penetration.

Furthermore, the substance has a high chemical stability, i.e. no hydrolyzability, no photo-oxidizability, no oxidizability, high thermostability and high welding resistance.

Furthermore, this substance is well tolerated and miscible with the common cosmetic and pharmaceutical formulation bases.

Due to its solubility profile, the substance mixes with oils and water, so it differs significantly from traditional cosmetic oils.

These properties now lead to a very high solubility of known light protection filters.

For example, it is known in the prior art that octyl triazone in cosmetic oils has only a very low solubility of at most 5% by weight.

% having.

The solubility of octyl triazone in ethyl 3- (N-butylacetamino) propionate is surprisingly about 50%. That when 20% by weight of 3- (N-butylacetamino) propionic acid ethyl ester is used, 10% by weight of octyl triazone can thus be incorporated into a formulation, which was previously not possible with other oils.

The following are listed as further, only exemplary, light protection filters which show a significantly improved solubility in ethyl 3- (N-butyl-acetamino) propionate:

Eusolex® 4360 (Benzophenone-3), Eusolex® 9020 (butyl methoxydibenzoylmethane), Eusolex® 6300 (4-methylbenzylidene camphor), 4-aminobenzoic acid (PABA), or also Eusolex® 232 (phenylbenzimidazole

Sulfonic Acid), which is actually water soluble! There is complete miscibility with all liquid UV filters such as Eusolex® 2292 (octyl methoxycinnamate), Eusolex® 6007 (octyl dimethyl PABA), Eusolex® HMS (homosalate) or Eusolex® OCR (octocrylene).

In general, it can be said that all light protection filters, the polarity of which lies between water and 01, dissolve particularly well in ethyl 3- (N-butylacetamino) propionate

Compared to conventionally used oils, 3- (N-butyl-acetamιno) -propιonsaureethylester is characterized by an excellent solution

It can be used to produce cosmetic preparations that have a significantly higher level of light protection filter

The preparation according to the invention is used as a sunscreen to protect the human epidermis or hair

The invention further relates to a method for protecting the skin and / or natural or sensitized hair from the sun's rays, a cosmetic preparation containing light protection filter being applied to the skin or the hair, the light protection filter being 3- (N-butylacetamιno) to improve the solubility. -propιonsaureethylester is used

"Sensitized hair" means hair that has been subjected to a permanent wave treatment, a color or decolorization process

If the cosmetic preparation according to the invention is used to protect human epidermis against UV rays, it is in various forms which are usually used for this type. It can be used, inter alia, as a lotion or emulsion, such as a cream or milk (W / O, O / W). , or in the form of oily or oily-alcoholic lotions, emulsions, such as cream or milk, in the form of oltg-alcoholic, oily-watery or wassπg-alcoholic gels or as solid sticks or be packaged as an aerosol

It can contain cosmetic adjuvants which are usually used in this type of preparation, such as, for example, thickeners, plasticizers, moisturizers, surface-active agents, emulsifiers, preservatives, anti-foaming agents, perfumes, waxes, lanolin, blowing agents, colorants and / or pigments that color the agent itself or the skin, and other ingredients commonly used in cosmetics

The light protection filters are generally present in an amount of 0 5 to 10%, preferably 1 to 8%, in particular 3 to 6%, based on the total weight of the cosmetic preparation. Combinations of different light protection filters can also be used

An oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof can be used as the solubilizing agent. The particularly preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycene and

Sorbitol

A preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and, apart from one or more light protection filters, is dissolved in ethyl 3- (N-butylacetamiono) propionate

Fatty alcohols, fatty acid esters, in particular triglycerides of fatty acids, fatty acids, lanolin, natural or synthetic oils or waxes and emulsifiers in the presence of water

Further preferred embodiments are oily lotions based on natural or synthetic oils and waxes, lanolin, fatty acid esters, in particular Tπglyceπden of fatty acids, or olig-alcoholic lotions based on a lower alcohol, such as ethanol, or a glycol, such as propylene glycol, and / or a polyol, such as Glycenn, and oils, waxes and fatty acid esters, such as triglycends of fatty acids The cosmetic preparation according to the invention can also be in the form of an alcoholic gel which comprises one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycene, and a thickener, such as silica. The oiig-alcoholic gels also contain natural or synthetic oil or wax

The solid sticks consist of natural or synthetic waxes and oils, fatty alcohols, fatty acids, fatty acid esters, lanolin and other fat bodies

The invention also relates to cosmetic sunscreens which contain at least one or more light protection filters, ethyl 3- (N-butylacetamino) propionate being used to improve the solubility of these light protection filters

If a preparation is packaged as an aerosol, the usual propellants, such as alkanes, fluoroalkanes and chlorofluoroalkanes, are generally used

If the agent according to the invention is intended to protect natural or sensitized hair from UV rays, it can be in the form of a shampoo, lotion, gel or emulsion for rinsing out, the respective formulation before or after shampooing, before or after coloring or decoloring, before or after the permanent wave is applied, or the agent is in the form of a lotion or gel for styling and treatment, as a lotion or gel for brushing or laying a water wave, as a hair lacquer, permanent wave agent,

Coloring or decolorizing agents for the hair. In addition to the compound according to the invention, this agent can contain various adjuvants used in this type of agent, such as surface-active agents, thickeners, plasticizers, preservatives, foam stabilizers, electrolytes, organic solvents, silicone derivatives, oils ,

Waxes, anti-greasing agents, dyes and / or pigments that color the agent itself or the hair or other ingredients commonly used for hair care

Even without further explanations, it is assumed that a specialist can use the above description to the greatest extent possible preferred embodiments are therefore only to be understood as a descriptive disclosure, and in no way as a limitation in any way.

The complete disclosure of all those listed above and below

Applications, patents and publications are incorporated by reference into this application.

The following test results and examples are representative of the present invention.

Examples

Example 1 5

The following table shows the solubility data of various UV filters in ethyl 3- (N-butylacetamino) propionate.

The solubility data were obtained as follows: 0 A supersaturated solution of a UV filter in 3- (N-butylacetamino) propionic acid ethyl ester is stirred overnight. A sample is taken from the supernatant solution and the content of the UV filter is determined.

5

J 7) Table 1: Solubility of various UV filters in 3- (N-butylacetamino) propionic acid ethyl ester

UV filter solubility

Eusolex® 4360 38% Eusolex® 6300 27% Eusolex® 9020 26% 4-aminobenzoic acid 17% Eusolex ® 232 (as Trissalz) 1%

Eusolex® 232 (as acid) 0.4% Uvinul® T 150 (octyl triazone) 50%

Example 2

For comparison, the solubility data of Eusolex® 4360 in various commonly used oils are shown in Table 2.

Table 2: Solubility of Eusolex® 4360 in different oils

Solvent solubility

Eusolex® 2292 19%

Homomenthyl salicylate 15%

Propylene glycol / dicaprate / dicaprylate 13%

C12-C18 alkyl benzoates 12%

Isopropyl myristate 8%

Octyl palmitate 5%

Liquid paraffin 2% Example A

A solution according to the invention for protection against insects and also against UV radiation, suitable for a pump spray, is produced from the following components:

% By weight

3- (N-Butylacetamino) propionic acid ethyl ester (1) 25.00 (Art. No. 1 1 1887)

Eusolex® 6300 (Art-No. 5385) (1) 20.00

Eutanol G (2) 15.00

Perfume oil 72980 (3) 0.30

Uvinul® T 150 (4) 5.00

Miglyol 812 (5) 15.00

Ethanol 96% (Item No. 100971) (1) ad 100.00

Manufacturing:

Eusolex® 6300 and Uvinul® T 150 are previously dissolved in ethanol and ethyl 3- (N-butylacetamino) propionate. The remaining components are added with stirring. The solution is then poured into a suitable pump spray system.

Sources of supply:

(1) Merck KGaA, Darmstadt (4) BASF, Ludwigshafen

(2) Henkel, Düsseldorf (5) Hüls Troisdorf AG, Witten

(3) Haarmann & Reimer, Holzminden Example B

A formulation for a roll-on to protect against insects and also against UV radiation is made from the following components.

% By weight

A 3- (N-butylacetamino) propionic acid ethyl ester (1) 15.00

(Art No. 1 11887)

Ethanol 96% (Item No. 100971) (D 50.00 Uvinul® T 150 (4) 5.00

B water, demineralized to 100.00

Klucel MF (2) 0.70 C propanediol-1, 2 (item no.107478) (1) 2.00

Arlamol E (3) 5.00

Manufacturing:

Phase A is solved beforehand. Phase B is stirred until Klucel is swollen. Phase C is introduced into phase B with stirring. Finally phase A is stirred in.

Sources of supply:

(1) Merck KGaA, Darmstadt (4) BASF, Ludwigshafen

(2) Aqualon, Düsseldorf (3) ICI, Essen

Example C

An oil according to the invention for protection against UV rays and insects is produced from the following components.

% By weight

Ethyl 3- (N-butylacetamino) propionate (1) 20.00

(Art-No. 1 1 1887)

Eusolex® 4360 (Item No. 105376) (1) 5.00 Eusolex® 9020 (Item No.) (1) 3.00

Eusolex® 6300 (Item No. 5385) 0) 4.00

Paraffin oil, thin (item no.107174) (1) ad 100.00

Miglyol 812 (2) 15.00

Cetiol B (3) 22.50 Eutanol G (3) 8.00

Manufacturing:

With stirring, all components are put together and heated until all components are dissolved. If necessary, perfume at 40 ° C.

Sources of supply:

(1) Merck KGaA, Darmstadt

(2) Hüls Troisdorf AG, Witten (3) Henkel, Düsseldorf

Example D

An oil according to the invention for protection against insects and UV rays can be produced by mixing and heating the following components with stirring until all components have dissolved. If necessary, perfume at 40 ° C.

% By weight

3- (N-Butylacetamino) propionic acid ethyl ester (1) 25.00 10 (Art. No. 1 1 1887)

Eusolex® 9020 (Item No. 105844) 0) 3.00

Uvinul® T 150 (2) 5.00

Low viscosity paraffin oil (item no.107174) (1) ad 100.00

Miglyol 812 (3) 15.00 15 Cetiol B (4) 22.50

Eutanol G (4) 8.00

Sources of supply:

(1) Merck KGaA, Darmstadt (4) Henkel, Düsseldorf 0 (2) BASF, Ludwigshafen

(3) Hüls Troisdorf AG, landlords

5

30

37) Example E

A cream (W / O) according to the invention which contains the insect repellent and two UV filters is produced from the following components.

% By weight A 3- (N-butylacetamino) propionic acid ethyl ester (1) 15.00

Eusolex® 9020 (Art-No. 105844) (D 2.00 Uvinul® T 150 (2) 5.00 0 Abil EM 90 (3) 3.00

Jojoba oil (4) 4.00 Cetiol B (5) 1.00 Prisorine 2021 (6) 2.00 Castor oil (7) 1.00 15 Lunacera W δO (8) 1.50

B Glycerin (item no.104093) (1) 2.00 sodium chloride (item no.106400) (1) 0.40 preservative q.s.

Water, demineralized ad 100.00 0

Manufacturing:

Phase A is heated to 75 ° C. and phase B to 80 ° C. Phase B is then slowly stirred into phase A, homogenized, and then under

Stir cooled. 5

Sources of supply:

(1) Merck KGaA, Darmstadt (5) Henkel, Düsseldorf

(2) BASF, Ludwigshafen (6) Unichema. Emmerich 30 (3) century Goldschmidt, Essen (7) Heess, Stuttgart

(4) Lamotte, Bremen (8) fountain pen, Lüneburg

37) Example F

An insect repellent cream (W / O) with additional UV filters is made from the following components.

% By weight

A 3- (N-butylacetamino) propionic acid ethyl ester (D 15.00

Eusolex® 4360 (Art-No. 105844) d) 5.00

Uvinul® T 150 (2) 5.00

Abil EM 90 (3) 3.00

Jojoba oil (4) 4.00

Cetiol B (5) 1.00

Prisorine 2021 (6) 2.00

Castor oil (7) 1.00

Lunacera W 80 (8) 1.50

B Glycenn (item no.104093) (1) 2.00

Sodium chloride (Item No. 106400) (1) 0.40

Preservatives q.s.

Water, demineralized ad 100.00

Manufacturing:

Phase A is heated to 75 ° C. and phase B to 80 ° C. Phase B is then slowly stirred into phase A, homogenized, and then cooled with stirring.

Sources of supply:

(1) Merck KGaA, Darmstadt (5) Henkel, Düsseldorf

(2) BASF, Ludwigshafen (6) Unichema, Emmerich

(3) Th. Goldschmidt, Essen (7) Heess, Stuttgart

(4) Lamotte, Bremen (8) fountain pen, Lüneburg Example G

% By weight

A 3- (N-butylacetamino) propionic acid ethyl ester 0) 20.00

Eusolex® 4360 (Item No. 105844) (1) 5.00

Eusolex® 6300 (Art-No. 5385) (1) 6.00

Homomenthyl salicylate (Item No. 1 1 1412) (D 5.00

Abil EM 90 (2) 3.00

Jojoba oil (3) 4.00

Prisorine 2021 (4) 2.00

Castor oil (5) 1.00

Lunacera W 80 (6) 1.50

B Glycenn (item no.104093) (D 2.00

Sodium chloride (Item No. 106400) (1) 0.40

Preservatives q.s.

Water, demineralized ad 100.00

Manufacturing:

Sources of supply:

(1) Merck KGaA, Darmstadt (4) Unichema, Emmerich

(2) Th. Goldschmidt, Essen (5) Lamotte, Bremen (3) Heess, Stuttgart (6) Füller, Lüneburg

Claims

PATENT CLAIMS

1 . Use of 3- (N-butylacetamino) propionic acid ethyl ester to improve the solubility of light protection filters.

2. Use according to claim 1, characterized in that up to 90% by weight of ethyl 3- (N-butylacetamino) propionate are used.

3. Cosmetic preparation containing light protection filter, characterized in that 3- (N-butylacetamino) propionic acid ethyl ester is used to improve the solubility of this light protection filter.

4. Cosmetic preparation according to claim 3, characterized in that up to 90 wt .-% 3- (N-butylacetamino) propionic acid ethyl ester are used.

5. A method for protecting the skin and / or natural or sensitized hair from the sun's rays, a cosmetic preparation containing light protection filter being applied to the skin or the hair, ethyl prop-3- (N-butylacetamino) propionate being used to improve the solubility of the light protection filter is used.