DE1952057A1 - Preparations for treating human skin - Google Patents

Description

Priority : from October 23, 1968 under the Serial HO. 770 116 in USA

The present invention relates to a topical composition comprising one or more esters of a branched chain contains aliphatic fatty alcohol and a hydroxy fatty acid and reduces heating when applied to the skin and prevents degreasing of the skin.

It has been recognized that soaps and detergents, when applied to the skin, severely degrease the skin. The result of this degreasing effect is a drying, runny and flaky condition of the skin, which in some cases can even be eczema-like.

009823/1930

_BA0

Recently, detergents have become more popular used in cosmetic preparations. cleaning supplies are used in relatively high concentrations in cleansers for the skin for removing make-up and facial cleansing as well as in shampoos, bubble bath preparations and so-called detergent cakes used. These cosmetic products containing detergents not only degrease the Skin, but also have a strong irritant effect on the skin.

Various attempts have been made in the past to reduce the drastic degreasing effects of detergents or to prevent surfactants. In the endeavor To avoid this degreasing effect, various types of fat materials, such as oils, fats, lanolin, Vaseline and the like. in combination with soaps and cleaning agents used. It was hoped that the addition of the fatty materials would enhance the degreasing effect by the deposition or precipitation of the fatty materials on the surface of the skin ala replacement of the sebum caused by the degreasing effect that cleaning agent ^ B was removed would prevent. the However, the addition of fat and fat-like materials to the surfactants was unsatisfactory, and the Effect was zero.

Asier® Ytreuolie -mir'den made, esters of fatty acids and

Monoprimary / alcohols in surface-active

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ßAD ORIGINAL

Incorporate funds. In the past, esters such as isopropyl myristic acid ester »butyl myristic acid ester, Propyl myristic acid ester, propyl palmitic acid ester, ethyl palmitic acid ester, Ethyl myristic acid ester and the like. used. These esters, however, showed none of the degreasing opposite effect, and when these esters off Alcohols with short molecular chains are formed, they increase the irritation of the skin. In addition, the! Have fatty acid esters the low molecular weight alcohols also have a solvent effect, and this solvent action serves to increase the degreasing effect of the detergent, what consequently also leads to an increase in irritation. Although fatty acids, such as myristic acid or palmitic acid, are found in human Skin sebum occur, after all, the low molecular weight alcohols that have been used in the esters in the past were, namely ethanol, propanol, laopropanol and butanol, not part of the skin metabolism, consequently these materials are premdatoffe and for the cells of the living skin provide additional irritation.

The present invention provides a material for local Application that is an ester of a branched chain, aliphatic Contains fatty alcohol and a hydroxy fatty acid. The ester is particularly suitable to be combined with a surface active agent such as a soap or a cleaning agent and when applied to the skin it works

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in such a way that it prevents degreasing of the skin. In some cases a film of greasy: material appears on it
deposited on the surface of the skin after the detergent was washed away from the skin. Another advantage is that the ester significantly reduces the irritative effect of the detergent or soap on the skin.

The esters of branched chain aliphatic fatty alcohols and hydroxy fatty acids are generally used in an amount of
0.05 to 50 Grew .- $ of the soap or detergent
and preferably used in an amount from $ 0.5 to $ 10. The soaps to which the esters are added are of conventional types which are metal salts of fatty acids.
Generally the metal salt is in the form of an alkali. salt, like '- "for example" of sodium or potassium, before,
and the fatty acids usually contain 12 to 20 carbon atoms. Sodium salts of coconut fatty acids are the most common soaps.

The detergent can be any commonly used surfactant. Examples of detergents that can be used are '. Alkali alkyl sulfates of
Formula ROSO ^ X, in which R is an aliphatic hydrocarbon radical with 10 to 18 carbon atoms and can be both saturated and unsaturated and X is sodium, potassium, lithium or another alkali metal. A specific example is sodium lauryl sulfate.

009823/1930

Another group of surfactants or detergents that can be used consists of the alkali alkylol sarcosinates, which have the general formula RCON (OH ₅ ) CH ₂ COOX, where R is an aliphatic hydrocarbon group having 12 to 18 carbon atoms and X is hydrogen or in Water-soluble sala-forming cation, such as sodium, potassium, lithium or the like, is,

Acetylenic glycols can also be used as surface-active agents, for example as described in the United States patent 2,997,447.

Other detergents or surfactants that Can be used are the water soluble higher alkyl aryl sulfonates, especially those having from about 8 to 15 carbon atoms in the alkyl group. For optimal effects it is

/ benzene preferred to use the higher alkyl sulfonate as a cleaning agent use, although other similar cleaning agents with a mononuclear aryl radical, such as toluene, xylene or phenol, can be used. The higher alkyl substituent on the aromatic No can have branched or straight chain structure have, and examples of such groups include the nonyl, decyl, Dodecyl, trideoyl and pentadeoyl groups, as seen from polymers derive low molecular weight monoolefins, deoyl, keryl and other groups.

009823/1930

- ο -.

The sulfate and sulfonate detergents can be in the form of their water-soluble salts, such as the alkali salts and stick- ' Substance-containing salts, such as, for example, the low molecular weight Alkyl or amine salts can be used. Examples are the sodium, Potassium, ammonium, isopropanolamine, mono- and trietharnolamine salts of these higher alkyl benzene sulfonates, higher alkyl sulfates etc. In industrial practice, it is preferred to use the alkali and / or ammonium salts.

Other suitable non-ionic cleaning materials are the alkanolamides of higher fatty acids, such as the monoethanolamides, Diethanolamides and isopropanolamides, in which the acyl radicals have about 10 to 18 carbon atoms. Examples are coconut acid (or equivalent lauric acid), capric acid, and Myristic acid diethanolamide, monoethanolamide and isopropanolamide.

It should be emphasized that the special soap or the special Detergents to which the ester is added for Invention is not critical and that the effect of the esters in terms of reducing the degreasing effect shows in all commonly used soaps and detergents.

The alcohol used in forming the esters is a branched chain, aliphatic, primary, secondary or tertiary fatty alcohol with a Seaamt carbon atom number im Molecule from θ to 20. Alcohols that have less than 8 carbon atoms « contained in the molecule »are not in contact with the skin

0098237 1930

turns and are alien to the cell metabolism. Alcohols with 20 carbon atoms or less in the molecule are preferred » to get an oily or pasty consistency for the alcohol.

The alcohol can be saturated or unsaturated. The branches are alkyl groups with 1 to 4 carbon atoms, such as ethyl, methyl, propyl, isopropyl, butyl and isobutyl groups. The branches can be on one of the carbon atoms of the straight chain.

Specific examples of alcohols that can be used are 4,6,8-trimethyloleyl alcohol, CC-ethylhexanol, 3,4-diisopropyl-i-hexadeoanol, 2,6-dimethyl-1-octanol | 2,6-dimethyl-1-octenolj 3,7,12, H-Ietrabutyl-i-octadecanolj 3,4-dipropyl-1-deoanolj 3,5-diethyl-i-unoecanol 5-methyl-7-ethyl-1- tridecanol; 2,6,8-triisobutyl-i-octadecanol etc. ₀

The fatty acid used to form the esters can be a straight chain or branched chain fatty acid of 5 to 20% Be carbon atoms in the straight or primary chain. If a branched chain fatty acid is used, then the branch will be an alkyl group of 1 to 4 carbon atoms and on any of the carbon atoms the straight line Chain lying.

The fatty acids can be either saturated or unsaturated

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and contain at least one hydroxyl group anywhere can lie along the straight carbon chain.

Specific examples of τοη acids that lead to the formation of the esters can be used are the following ι 12-Hydroxyoctade-censäurej Trihydroxystearic acid; Dihydroxystearic acid j tf-hydroxy-n-dooosanoic acid; Ä-Hydroxy-n-tetracosanoic acid j Si -hydroxy-n-hexacoic acid j 5-hydroxy-3-butyl-heptadecanoic acid ι 3-hydroxy-3-propyl-oetadecanaäurej 3-hydroxy-3-ethyl-nonadecanoic acid etc.

-Special examples-τοη'Estern, which are formed by the implementation of the Terzweigtkettigen Eliphatisehen "primary" Pettalkohole and ", the" Hydrogen fatty acids ", aiaä the following: - ^ -i ^ -cLro ^ -ootadscenyl-fiC-äthyl-iiösaiiat j" i ^ '- Hydroxy-oetadleoenyl-2 ₉ S-dimethjl- © ctaaati, Ä-Bydroxy-a-hexacosanyl-J »?» 12,14-tetra-'Dutyl-octadecaaat _r Ä-Hydroxy-n-docosanyl-2 »β-, 8-triisobutyl- ~ octadecanat's bihydroxy-stearyl-3» 5-diethyl-undeeanate, 3- methyl-12-kyte Xy-stearyl-> α-ethyl-hexanate _r St -lthyl-12-hydroxyoetadecanyl-2 _s 6-dimethyl-octanate j tri-hydroxy-stearyl-flf-ethylhexanate, 12-hydroxy-ootadecenyl-3,5-diethyl -undeeanate, 2,5-butyl-IÖji ^ -di-hydroxy-hexadecanyl-Öf-ethyl-hexadecanate etc. *

The way in which the esters are prepared is not critical, and in general, the acids and alcohols are only reacted in equimolar amounts.

1fie noted above, contain many cosmetic products

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. , ■ BAD ORIGINAL

substantial amounts of detergents and are due the high percentage of these detergents are irritating to the skin. For example, the following conventional cosmetic products contain the cleaning agents listed and have the indicated irritation index;

009823/1930

jA ¹ Ai ^; '■:' ■■■■} 'Ίί \ &

TABLE I.

Cosmetic
product

Cleansing Lotion

Detergent type

of the included
Detergent

Lauryl-cycloimidinium-1-ethoxyethionic acid-2-ethionic acid disodium salt

20.0

Irritation index

shampoo Eatrium Lauryl
ether sulfate 30.0 4.08 Egg shampoo Sodium lauryl
ether sulfate 29.3 3.77 foam bath T riäthanolamin-
lauryl sulfate 46.0 4.17 Skin cleanser anionis ches, two-
baaiaches S-acid
half-ester sulfonate 55.0 3.52 facial
Niger substituted
Alkylamine of
Lanolic acids 52.0 5.23

4.45

cleaning gel

Lauryl-oyclo-imi- 25.0 Dinium-1-ethosyethionic acid-2-ethionic acid-disodium salt

+ amphoteric upper 25 »0 surface active smock with a ß-enalt on carboxyl and amine groups

5.46

Perireiaige τ

sodium lfturyl sulfate 5O ₅₁ O

5.13

100.0

2.75

9823/1830

The irritation index is; calculated according to the method "the in "Appraisal of the Safety of Chemicals in Foods, Drugs and Cosmetics". An irritation index of 0 to 2 means slight irritation, an irritation index of 2 to 5 means moderate irritation, and an index above 6 means strong irritation.

From Table I it can be seen that many conventional cosmetic products contain substantial amounts of detergent which when applied to the skin cause degreasing of the skin and irritation.

A series of "adjustment _g durchgefükrfe the Sntfettungswirkung on menseüXlÄe skin (I") conventional cleaning agents alone, (1-5 "stit he TkSmvti. Lohen fatty materials combined Reinigungsmi'jyela Anoe. (III) with the esters of branched, aliphatic compare _s -prissärär lettalkohole and hydroxy united detergent. In carrying out these comparative tests Uatriumlaurylsulfat was as a cleaning agent used, and -were than conventional fat-like materials Iriglyceride, such as castor oil or peanut oil, and esters of straight-chain alcohols, such as / octanol, used.

In carrying out these tests, a 10 cm area of skin was exposed on the outside of the forearm of a test pereon degreased by covering the surface with degreased,

009823/1930

cotton wool soaked in ether. The cotton wool; balls were extracted with ether, the ether evaporated under vacuum, and the residual Hauttalgrückstand was dried in an oven at 9O ⁰ C, was until constant weight attained. This gave the sebum content of the skin surface.

A nearby-area of skin of the same size was found then treated with one of the aqueous detergent solutions. For this purpose a glass cylinder was placed on the Skin attached, with the skin forming the bottom of the cylinder. 5 ml of the test solutions were in the cylinder filled in and moved over the surface of the skin by shaking the arm for 10 minutes. The detergent solutions were then removed from the cylinder and the skin was removed Rinsed 3 times with 5 ml of distilled water. After rinsing, the cylinders were removed and the skin with a warm Airflow dried. After drying, the sebum content of the treated skin was determined in the same way as described above, certainly. The results of the comparison are shown in the following table? '

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Treatment
solution TABLE II io sebum
loss io upper
area-
fat gain attempt
No. no
5 ^a / ° sodium
lauryl sulfate Sebum
Salary ₂
of 10cm
Upper skin
area 8.7 1. no
lauryl sulfate
0.55 ^ olive oil 2.3 mg
2.1 mg 28.6 - 2. no
4,5 / ^ sodium
lauryl sulfate
$ 0.5 peanut
oil 3.5 mg
2.5 mg 37.2 3. no
4.5 # sodium
lauryl sulfate
0.5 ψ castor
oil 3.5 mg
2.2 mg 18.5 4th 2.7 mg
2.2 mg

no

3.1 mg

lauryl sulfate 0.5 ^ octyl-12-hydro ^ ystearate 1.9

38.8

none 3.1 mg

4.5 / ^ sodium lauryl sulfate

0.5 ^ 0ctylricino-

leat 2.4 mg

22.6

00 98 2 3 / ta 30

7. none 2.7 mg - -

4.5% sodium lauryl sulfate

0.5% ethylhexyl 12-hydroxy stearate 3.1 mg - +14.8

8. none - 2.5 mg - -

4.5% sodium lauryl sulfate

0.5% 2,6-dimethyloctyl- 12-rhydroxy-

stearate 2.8 mg +12.0

9 none 2.5 mg - -

4.5% sodium lauryl sulfate

0.5% α- ethyl- - - ■

liexylrioinoleate 2.5 mg 0

10. none 2.8 mg

lauryl sulfate

0.5% 2,6-M-methylloctyl-

ricinoleate 2.8 mg 0

From the above experiment Uo. 1 it can be seen that the treatment of the skin with an aqueous solution of 5% sodium lauryl sulphate resulted in a 8.7% loss of sebum, while experiments Nos. 2 and 3, in which olive oil and peanut oil, respectively, were used together with sodium lauryl sulphate , led to a significantly higher percentage of sebum loss, namely 28.6 and 37.2 fo , respectively. According to experiment no. 4, the combination of sodium lauryl sulfate and caator oil resulted in an 18.5% loss of sebum during the treatment of the skin

00 982 3/19

with the combination of sodium lauryl sulfate and esters of straight-chain fatty alcohols and hydroxy fatty acids to a sebum loss of 38.8 and 22.6 $ i "led, as in Experiments No. 5 and 6 is shown.

Trials No. 7 to 10 in Table II were carried out according to the invention and show the addition of an ester of a branched-chain aliphatic fatty alcohol and a hydroxy fatty acid. Specifically, the treatment solution of experiment no. 7 did not result in any loss of sebum from the skin and actually resulted in the deposition of a film of fat, as can be seen from the 14.8 $ increase in fat shown in the table. Similarly ise W _e, the treatment resulted in the skin with the solution of the experiment No. 8 to a 12 # increase in surface fat. In experiments No. 9 and 10 there was no sebum loss, but no additional fat deposit was obtained on the skin in these experiments.

Table II shows the surprising and unusual effect the esters of branched-chain aliphatic fatty alcohols and hydroxy fatty acids in preventing the degreasing effect of detergents or materials that contain detergents contain. It will not only have this degreasing effect switched, but in some cases you even got one. Increase in the surface fat content.

009823/1930

The following table shows the decrease in primary irritation of sodium lauryl sulfate through the addition of esters of aliphatic, branched chain fatty alcohols and hydroxy fatty acids.

■ TABLE III

attempt
No. aqueous treatment solution
I. Irritation index 1. 1,4.5 4.28 2. 5 #] 3.56 3. fo sodium lauryl sulfate 3.06 4th E sodium lauryl sulfate 2.73 5. $ 4.5 Sodium Lauryl Sulphate
$ 0.5 2,6-dimethyl-octyl-
hydroxystearate 2.57 6th 4.5 y
0.5 ί 2.45
ι % Sodium Lauryl Sulphate
1o OC ethyl hexyl ricinoleate $ 4.5 Sodium Lauryl Sulphate
0.5 # 2,6-dimethyl-octyl-
ricinoleate 4,5 ^ Sodium Lauryl Sulphate
0.5 ^ flf-ithylhexyl-12-
hydroxystearate

The irritation index was determined according to the method in "Appraisal of the Safety of Chemicals in Foods, Drugs and Cosmetics ".

As shown in Table III, a 1,4 ^ aqueous yielded Solution of sodium lauryl sulfate has an irritation index of 4.28,

0098 23/1930

while a larger amount of the detergent, namely 5 fo, was used in experiment No. 2 resulted in a lower irritation index of 3.56. The addition of the branched-chain fatty alcohol esters of hydroxy fatty acids, which were used in experiments no. 5, 4, 5 and 6 reduced the irritation index in all cases much more than sodium lauryl sulfate alone, as in experiment no. 2 is shown. The smaller amount of the cleaning agent in experiments 3 to 6 compared to experiment 2 played no role in the reduced irritation, because comparative experiments no. 1 and No. Figures 2 show that a decrease in the percentage of detergent results in an increase rather than a decrease in irritation.

The results of the T _a ble III show the unusual and surprising property of the ester verzweigtketbiger aliphatic fatty alcohols and hydroxy fatty acids in reducing the irritant effect of the cleaning agent to the human skin.

The following examples illustrate various products that include soaps and detergents as well as the Ister aliphatic contain branched-chain fatty alcohols and hydroxy fatty acids, the amounts being given in Grew "- # *

1. Soap

Sodium Salt of Coconut Fatty Acid $ 89

^ -Hydroxy-octadecanyl- flt-ethyl-hexanate 11 ^ έ

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2. Cleansing cream

Distilled water 40%

Sodium lauryl sulphate 55 %

Gf-Hydroxy-n-docosanyl-2,6,8-triisobutyl-

octadecanate 5 5 ^

3 «shampoo

Lauryl Monoglyceride Ammonium Sulphate $ 20

Triethanolamine OJ / »

12 ~ Hydroxy-ootadecenyl-2,6-dimetliyl-

ootanate 12.5%

distilled water $ 66.8

nail polish remover

Ethyl acetate 85 i <>

3-methyl-12-hydro: x: stearyl-flf-ethylhexanate 9 »5 °

distilled water "5» 5 i °

5. Face cream

Iianolin alcohols 10.0 ^

Lanolin 20.0 ^

light mineral oil 35.0 ^

2,5-butyl-10,12-dihydroxyhexadecanyl

Ä-ethyl-hexadeanate 20.0 ^

distilled water 14.8 i <>

Methylpropyl paraben 0.2%

6. Hand lotion

G-lyeeryl monostearate 1 96

Isopropyl palmitate Λ ία

Polyethylene glycol ^ OO-distearate 2 #

Di-hydroxystearyl-3,5-diethyl undecanate Ί $>

Glycerin 10 96

009823/1930

Methyl paraben Sodium cetyl sulfate distilled water

7. Dishwashing detergent distilled water alkyl polyglycol ether sulfate sodium lauryl sulfate ethanol

12-hydroxy-octadecanyl- CL -ethylhexanate

8. Detergent Dodecylbenzyl sulfate Tetrapropylene benzene sulfate Trisodium phosphate Sodium carbonate Carboxymethyl cellulose

12-Hydroxy-octadecenyl-2,6-dimethyloctanate distilled water
Sodium tripolyphosphate

The esters of aliphatic branched chain alcohols and Hydroxy fatty acids can be applied directly to the skin or they can be combined with any material that has a degreasing effect on human skin, such as surfactants, solvents, .atetringents, etc. In addition, the Seter can be used in a variety of cosmetic and pharmaceutical products as well as in cleaning products, such as detergents and dishwashing detergents, how by

009823/1930

1952057 "Ό, 1 ok 5, ο io 70 9 io 70 io · 10 i> 10 ok 5 ok 5 $> 10 ok 10 ok 40 ok 10 ok 2 ok VJI ok 10 ok 13th ok

the above examples have been explained.

0 0 98237 1930

Claims (7)

PATENT CLAIMS 1. Anti-irritation and degreasing of the human Skin-preventing agent, characterized by a content of at least one ester of an aliphatic, branched chain fatty alcohols having at least 8 carbon atoms in the molecule, where the branches are alkyl groups of 1 to 4 carbon atoms, and one Hydroxy fatty acids. 2. Means according to claim 1, gekennzeichnei ^ urch. a salary at least one ester of straight or branched chain Fatty acids. 3. Means according to claim 1 and 2, characterized by the content of at least one ester of a fatty acid with 5 to 20 carbon atoms. 4. Means according to claim 1 to 3, characterized by the content of at least one ester of an alcohol with 8 to 20 carbon atoms. 5. Means according to claim 1 to 4 »characterized in that that it contains the prayers in an amount from 0.05 to 50. 6. Composition according to claim 1 to 5, characterized in that it is 2,6-dimethylootyl-12-hydroxystearate as Beter ^ a -, + 009823/1930 contains. 7. Use of the agent according to claim 1 to 6 for prevention the degreasing effect and to reduce the irritating effect of surface-active materials on human skin. 009323/1930 BATH ORIGINAL