US3886287A - Cosmetics containing saturated, branched synthetic higher hydrocarbon - Google Patents

Cosmetics containing saturated, branched synthetic higher hydrocarbon Download PDF

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US3886287A
US3886287A US36337273A US3886287A US 3886287 A US3886287 A US 3886287A US 36337273 A US36337273 A US 36337273A US 3886287 A US3886287 A US 3886287A
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eicosane
trimethylbutyl
trimethyl
octyl
ethyl
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Susumu Kobayashi
Kenichi Tomita
Hakuji Katsura
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Shiseido Co Ltd
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Shiseido Co Ltd
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/31Hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C9/00Aliphatic saturated hydrocarbons
    • C07C9/22Aliphatic saturated hydrocarbons with more than fifteen carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74Biological properties of particular ingredients
    • A61K2800/75Anti-irritant
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • A61Q1/04Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06Lipsticks
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/937Dispersion or emulsion
    • Y10S514/938Oil-water type
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/969Ointment or salve base

Abstract

Cosmetics having a quality similar to that of the conventional cosmetics containing squalane, are prepared using at least one saturated, branched synthetic higher hydrocarbon having 26 to 48 carbon atoms, of the formula:

WHEREIN R1, R2, R3 and R4 represent an alkyl group of 2 to 15 carbon atoms, and R1 is different from R2 and R3 is different from R4, and other cosmetic additives.

Description

United States Parent Kobayashi et al.

COSMETICS CONTAINING SATURATED, BRANCHED SYNTHETIC HIGHER HYDROCARBON Inventors: Susumu Kobayashi; Kenichi Tnrniia;

Hakuji Katsura, ah of Yokohama.

Japan Assignee: Shiseido C0., Lid., Tokyo, Japan Filed: May 24, 1973 Appl. No.: 363,372

Foreign Application Priority Data Oct. 6, 1972 Japan 47-100400 US. CI. i i i i 4 i i. 424/358; 424/63; 424/64;

424/70 Int. C'I. AGIK 7/00 Field Of Search H 424/63, 70, 64, 388

References Cited UNITED STATES PATENTS i2/i962 Monot 424/358 May 27, 1975 FOREIGN PATENTS OR APPLICATIONS 40-9995 5/1965 Japan 424/358 Primary Examiner-Frederick E. Waddell Attorney, Agent. or FirmPauI & Paul CHCH CH CH wherein R R R; and R represent an alkyl group of 2 to 15 Carbon atoms, and R is different from R and R is different from R and other cosmetic additives.

4 Claims, N0 Drawings 1 COSMETICS CONTAINING SATURATED, BRANCHED SYNTHETIC HIGHER IIYDROCARBON The present invention relates to cosmetics, more par ticularly, relates to cosmetics containing as a cosmetic base, a synthetic higher hydrocarbon having excellent physiological properties.

Broadly speaking, the conventional cosmetic contain a cosmetic base consisting of saturated higher hydrocarbons selected from higher mineral hydrocarbons, for example, liquid paraffins, higher animal hydrocarbons, for example, squalane which is prepared by completely hydrogenating squalene obtained from fish liver oil, and higher vegetable hydrocarbons, for instance, completely hydrogenated terpenes and polymerized terpenes.

The liquid mineral paraffins consist of a mixture of multiple component hydrocarbons, varying in molecular weight and chemical structure. Sometimes, some of the component hydrocarbons stimulate human skin and are easily decomposed by the action of microorganisms. Accordingly, the liquid paraffins guarantee little in cosmetic quality, that is, they neither ensure non-irritation to human skin nor stability during prolonged storage.

The vegetable hydrocarbons also include a plurality of component hydrocarbons varying in number of carbon atoms and chemical structure. Therefore, the vegetable hydrocarbons sometimes include undesirable component hydrocarbons having considerable stimulating effect on human skin and low resistance to miere-organisms.

It is known that squalane is a simple higher animal hydrocarbon of 30 carbon atoms and does not stimulate human skin and has an excellent stability in storage. However, since the squalane is prepared from squalene include in fish liver oil which is not always readily available, the supply of squalane is limited and variable in quantity.

Due to the above-stated circumstances, it is strongly desired by the cosmetic industry that uniform qualityhigher hydrocarbons usable as the cosmetic base, producing non-irritation of human skin and having high stability in relation to biological activity can always be obtained in a desired quantity without difficulty. For

this purpose, it is desirable to obtain simple synthetic higher hydrocarbons having similar cosmetic properties to those of squalane.

One object of the present invention is to provide cosmetics comprising, as a cosmetic base, a synthetic higher hydrocarbon having a non-stimulative property, a high stability to the action of micro-organisms, and other physiological properties.

The other object of the present invention is to provide cosmetics, for example, skin, hair, make-up, bath and toilet cosmetics, comprising a cosmetic base effective for protecting the human body from the action of micro-organisms, with sufficient safety.

The above-stated objects are accomplished by the cosmetics of the present invention. The cosmetics of the present invention comprise a base consisting of at least one saturated, branched synthetic higher hydrocarbon having 26 to 48 carbon atoms, of the formula:

H it

CHCH CH CH wherein R,, R R and R represent an alkyl radical of 2 to 15 carbon atoms, but R, differs from R, and R, differs from R and other cosmetic additives.

The synthetic higher hydrocarbons usable for the present invention are ideal for the cosmetic base.

That is, the synthetic higher hydrocarbons of the present invention can eliminate the above-mentioned drawbacks of the conventional cosmetic base, and be stored for a prolonged period without deterioration. Also, the synthetic higher hydrocarbons of the present invention are greatly effective for protecting human skin from chemical and physical stimulation, preventing the penetration of micro-organisms into the human body, and maintaining human skin in a normal physiological condition even if circumstance changes.

Table 1 indicates physical properties of the typical synthetic higher hydrocarbons usable for the present invention. Further, Table 1 shows the physical properties of the synthetic hydrocarbons of less than 26 carbon atoms and squalane. namely, 2,6,10,15,19,23- hexamethyl-tetracosane.

Table l Viscosity S cific Freezin Bo'l' t "C Hydrocarbon Formula (cps) at ge vity point z mg pom 25C at 19C (C1 Pressure (mmHg) 2,2,4-trim ethyl- 1 0-ethyl- 7(1,3.3-tr|methy1butyl)- C l-l 35.0 0.7980 S )]1 getraldecaane I d -et y -octy octa ecane C ll 24.2 0.8082 s 80 200 2 2, 2,4-tr|methyl-7( 1,3,3- C ll 20 24 190 210352 Th tnmethylbutyl] eicosane Present 9,12-dihexyl eicosane C H 31.5 0.8230 s 8 (180 210)]1 Invention hexaethyl eicosane C,,,H 72.5 0.8173 80 (230 240)]2' 5-ethy180decyl eicosane c H 33.1 0.8106 2,2,4,13,ISJS-hexarnethyb n m s I5 (235 256) 7,lO-bis( 1,3,3-trirnethyl- C H 63.6 08159 B lsufiybhexadecane 0 (I80 200),")

exyl-lZ-octyl docosane C,,,H 42.6 0.8140 3 2, 2,4-trimethyl-7-( 1.3.3 (200 2 I SW0 2 trrmethylbutylJ-lO-octyl C ll, 59.7 0.8160 3-2 (200 215)]10 eicosane ll,14-dioctyl tetracosane C l'l 52.5 0.8169 7.5 10.5 (200 220/10" 9-hexyl:l Z-decyl tetracosane C li 53.0 0.8171 9.0 13.5 (210 230)]10" 2,2,4-tr|methyl-7-( 1,3,3-

trimethylbutyl l O-decyl dooosane 3 l 4 Table 1 --Continued Viscosity Specific Freezing Boiling point tC) Hydrocarbon Formula (cps) at gravity point 25C at 19C ((1') Pressure (mmHg) 1 LoctyLH-decyl hexacosane C H 22 30 (230 245 N10" 13,16-didecyl octacosane C H 35.5 45 {250 2707/10 5,8'diethyl dodecane C H 4.5 0.7798 s-80 (150 l55l/32 ther than the 5-ethyl-8-hexyl hexadecane Cn sa 16.0 0.7961 S-80 (150 160)]2 present invention 2,6,l0,l5,l9,23-hexamethyl C H 35.0 0.8068 S-50 (230 240)]2 tetracosane The synthetic higher hydrocarbons usable for the present invention are prepared, for example, by the procedures detailed below.

Preparation of the Synthetic Higher Hydrocarbon Usable for the Present Invention The synthetic higher hydrocarbons usable for the present invention include 26 to 48 carbon atoms. The hydrocarbons of less than 26 carbon atoms are not to be considered for the cosmetic base because of too low viscosity and excessive stimulation to human skin. Also, the hydrocarbons having more than 48 carbon atoms are unsuitable for use as cosmetic base because of excessive viscosity and poor spreadability.

The synthetic higher hydrocarbons usable for the present invention may be prepared by the conventional methods for synthesizing alkane compounds. For example, the synthetic higher hydrocarbons may be prepared in accordance with the Wurtz reaction or Frankland reaction. That is, two saturated branched hydrocarbon halides of the formula:

cacn x and xcn ca 1. Preparation of 2,2,4-trimethyl-lO ethyl-7( l,3,3-trimethylbutyl)tetradecane and 2,2,4,13,15,]5-hexamethyl-7,l0-bis(1,3,3- trimethylbutyl)hexadecane The above mentioned hydrocarbon compounds were prepared by condensing Z-ethylexyl bromide and 5,7,7- trimethyl 2(l,3,3-trimethyl-butyl)octyl bromide.

The lethylhexene-Z-al-l was prepared by condensing n'butylaldehyde in an aqueous solution of 2% by weight of sodium hydroxide, and then, converted to 2' ethylhexanol by hydrogenating in the presence of a raney nickel catalyst. A mixture of one mol of Z ethylhexanol and 2.1 mols of hydrobromic acid (which was an aqueous solution of more than 47% of hydrobromic acid, having a specific gravity of 1.48) was charged into a one litre, three neck flask, and then, 1 part by mol of concentrated sulfuric acid was added by drops while the flask contents were being cooled with ice. Thereafter, the reaction mixture was gradually heated while stirring to a temperature of C and maintained at that temperature for 6 hours. The reaction product was diluted with hexane, successively washed with water, concentrated sulfuric acid, water and thereafter, an aqueous solution of sodium carbonate, dried over calcium chloride and then, distilled.

2-ethylexy1 bromide having a boiling point of 84 to 86C, under a pressure of 15 mmHg, was obtained in an amount of 167 g (yield: 86.5%).

The 5,7,7-trimethy1-2( 1,3 ,3-trimethyl-butyl)octy1 bromide was prepared by the following procedure.

3,5,5-trimethy1-hexyl aldehyde was prepared from isooctene by OXO synthesis (hydroformylation) and then, converted to 5,7,7-trimethyl-2(1,3,3-trimethylbutyl) octanol by the aldol condensation process. The 5,7,7-trimethy1-2(1,3,3-trimethyl-butyl) octanol was converted to butyl)octyl bromide having a boiling point of 120 128l2 mml'lg by reacting with the hydrobrornic acid in the same procedure as that of the Z-ethylhexyl bromide, in an yield of 72.7%. The condensation of the 2- ethylhexyl bromide with the 5,7,7-trimethyl-2 (1,3,3-trimethylbutyl)octyl bromide was effected by the following procedure.

A 100 ml three neck flask was charged with a reaction mixture of 0.085 mol of the 2-ethylhexyl bromide and 0.085 mol of the 5,7,7-trimethyl-2( 1,3,3-triinethyl butyl)octyl bromide. 0.187 mol of metallic sodium was added to the reaction mixture, which was being cooled with ice and stirred for 5 hours under the cooled condition. The non-reacted metallic sodium was treated with methanol and water. The reaction product was dried with anhydrous sodium sulfate and then distilled to iso' late the resultant hydrocarbon compounds from each other. By the distillation, (A) 5,8-diethyl'dodecane having 14 carbon atoms, a boiling point of 350 C/32 mmHg, a viscosity at 25C of 45 cps, a specific gravity at 19C of 0.7798 and a freezing point of lower than -80C was obtained in a yield of 9.8%, (B) 2,2,4-trimethyl 10-ethyl-7( l ,3,3'trimethyl-butyl)tetradecane having 26 carbon atoms, a boiling point of C/1 mmHg, a viscosity at 25C of 35.0 cps, a specific gravity at 19C of 0.7980 and a freezing point of lower than 80C was obtained in a yield of 78.4% and (C) 2,2,4,13,15,15-hexamethyl-7,10-bis(1,3,3- trimethylbutyl)hexadecane having 36 carbon atoms, a boiling point of 180 200C/10 mml-lg, a viscosity at 25C of 636 cps, a specific gravity at 19C of 0.8159 and a freezing point of lower than -80C was obtained in a yield of 10.0%.

The hydrocarbon compounds (B) and (C) thus obtained are novel compounds of the present invention and have the formulae (1) and (ll).

5,7,7-trimethyl-2(1,3,3-trimethyl- 2. Preparation of 9,l2dihexyl eicosane The 9,10-dihexyl eicosane was prepared by condensing 2-hexyldecyl chloride which was obtained in the following procedure.

2-hexyl decanol was prepared from n-octylaldehyde in the same procedure as that of the 2-ethyl hexanol in Example 1. A reaction mixture of 2 mols of the 2- hexyldecanol and 3.mols of pyridine was charged into a 2 litre three neck flask and 2.4 mols of thiony] chloride were added by drops while the mixture was stirred and cooled with ice. After completing the addition of the thionyl chloride, the reaction mixture was heated at a temperature of 120 to 140C for 8 hours. The reaction product was diluted with hexane, successively washed with concentrated sulfuric acid, water and an aqueous solution of sodium carbonate, dried with anhydrous sodium sulfate and then distilled. By the distillation, 2-hexyldecyl chloride, with a boiling point of l20 125C/3 mmHg was obtained in an amount of 276 g (yield: 53%).

The Z-hexyldecyl chloride thus obtained was converted to 9, l 2-dihexyleicosane by the following procedure.

The 2-hexyldecyl chloride in an amount of 0.274 mol was charged into a 200 ml three neck reaction flask, 0.275 mol of metallic sodium was added, while stirring, at room temperature and then maintained at a temperature f l to 140C while stirring for 2 hours. Thereafter, the reaction mixture was heated at a temperature of 130C for 8 hours. The non-reacted metallic sodium was deactivated with ethanol, The reaction product was diluted with hexane, washed with water, dried with anhydrous sodium sulfate and then, distilled. By the distillation, boiling -dihexyl eicosane having 32 carbon atoms, a boiiling point of l 210C/l 2 mmHg, a viscosity at 25C of 31.5 cps, a specific gravity at 19C of 0.8230 and a freezing point of lower than 8.0C was obtained in a yield of 35%. The 9,12-dihexyl eicosane is a novel compound of the present invention and has the following formula I): cu.

cuca ca ca (cm) (ca )r 3. Another Preparation of 9,l2-Dihexyl Eicosane The 9,12-dihexyl eicosane was prepared by condensing Z-hexyldecyl bromide,

The 2-hexyldecyl bromide was prepared from 2 hexyl decanol using the same method as that of 2 ethylhexyl bromide in Example 1. i

A 500 ml three neck reaction flask was charged with 0.l mol of metallic magnesium and a small amount of iodine, and a small amount ofthe 2-hexyldecyl bromide was added by drops. Thereafter, a solution of 0.2 mol of the Z-hexyldecyl bromide in 200 ml of anhydrous ether was further added by drops into the reaction flask. The reaction mixture was heated at a tempera ture of 55 65C for 24 hours while refluxing, and

then, the ether was distilled away from the reaction mixture. Next, the reaction mixture was maintained at a temperature of 120C for 48 hours. The reaction product was treated with hydrochloric acid, extracted by hexane, dried with anhydrous sodium sulfate and then, distilled. As a result of the distillation, 9,12-

dihexyleicosane having the same physical properties as those in Example 2 was obtained in a yield of 20%.

4. Preparation of l l,l4Dioctyl Tetracosane The above-captioned hydrocarbon compound was prepared by condensing 2-octyl dodecyl bromide which was prepared by the following procedure.

A mixture of 2-octyl dodecanol and the sodium salt of n'nonanoic acid was prepared by heating n-decanol at a temperature of 200 to 230C in the presence of sodium hydroxide. From the mixture, 2-octyl dodecanol was isolated by extraction and distillation. The 2-octyl dodecanol thus obtained, was converted to 2- octyldodecyl bromide having a boiling point of 175 185C/3 mml-lg by treating with hydrobromic acid in the same as that for 2-ethyl hexanol in Example 1.

The condensation of the 2-octyldodecyl bromide was carried out by heating together with metallic sodium at room temperature for 16 hours, at 55C for 6 hours and then, at 150C for 4 hours. The condensation product was treated in the same method as that for the condensation product in Example I. As a result of the treatment, 1 l ,14-dioctyl tetracosane having 40 carbon atoms, a boiling point of 200 220"C/' mml-lg, a viscosity at 25C, of 52.5 cps, a specific gravity at 19C of 0.8169 and a freezing point of 7.5 105C was obtained in a yield of 74%.

The hydrocarbon compound thus prepared has the following formula IV:

CHCH CH CH l. Stimulation of Animal Skin by One Application For each of the six kinds of synthetic higher hydrocarbons as shdwn in Table 2, eight albino rabbits were used. They were divided into two groups of four and their hair was cut at the portion to be tested. The rabbits in one of the groups had their skin scraped from the test portions. However, the skin of remaining rabbits was kept intact. All the rabbits were secured by immobilizing equipment. The six kinds of synthetic higher hydrocarbons'shown in Table 2 were applied, in an amount of 0.5 ml. onto a 2.5 cm square piece of lint fabric. The lint pieces bearing the synthetic higher hydrocarbons were put on the test portions of the rabbits so as to bring the applied synthetic higher hydrocarbon layer into contact with the skin. The lint pieces were covered by 3.5 cm square gauzes secured onto the test portions by adhesive tapes and further completely covered by rubber dams. The rabbits were maintained for 72 hours under the above-mentioned test conditions. After 24 hours the lint pieces on the rabbits were removed and the test portions were observed for red spots (erythemata) and dropsical swellings (edemata). The erythemata and edemata thus observed were valued in accordance with the predetermined evaluation standards as detailed hereinafter. Thereafter, the lint pieces were re-applied for the remaining 48 hours. After the testing was completed, the same evaluation as stated above was repeated.

Evaluation Score for Erythema Erythema Score No erythema 0 Slight erythema 1 Clear erythema 2 Extreme erythema 3 Extreme erythema and slight desquamation 4 Evaluation Score for Edema Edema Score No edema 0 Very small edema 1 Small Edema 2 Edema of about 1 mm diameter 3 Extreme edema larger than lint piece 4 The respective results of evaluations for the erythema and edema were combined and averaged, and

those averaged values for the erythema and edema were again averaged. The averaged values were estimated as follows.

Estimation of the averaged values The results are shown in Table 2.

2. Irritation of Animal Skin by Three Applications For each of the synthetic higher hydrocarbons, three guinea-pigs were used. Their hair was cut at the portion to be tested. The synthetic higher hydrocarbon was applied in an amount of 0.3 ml onto the test portion. After testing for 24 hours, the same application of the synthetic higher hydrocarbon as stated above was repeated twice onto the test portion.

After the test was completed the test portions of the guinea pigs were observed for erythemata and edemata formations. The observed erythema and edema were valued in accordance with the same evaluation standards as those stated hereinbefore. The results are shown in Table 2.

For comparison, the same test as those stated above were repeated using the liquid paraffin, squalane, 5,8- diethyl dodecane and 5-ethyl-8-hexyl hexadecane. The results are shown in Table 2.

Table Z-Continued Stimu- Stimulation lation umber of albino of guineaof rabbit skin pig skin carby one by three Hydrocarbon bon application applicaatom trons 2,2,4-trimethyll-ethyl-7- (1,3,3-tri- 26 0. l9 1.4 methylbutyl) tetradecane -ethyl-8- octyl 28 0 0.33 octadecane The 2,2,4-tri present methyl-7- (l,3,3-tri- 30 0 0.33 invenmethyl-butyl) tion eicosane 9 l Z-dihexyl eicosane 32 0 0.33 2,2,4.l3,|5,l5- hexamethyl-7, 10- bis( l,3,3-tri- 36 O 0.19 methylbutyl) hexadecane l 1,14-dioctyltetracosane 40 0 0. l 9

Average Liquid Other paraffin 20 0.69 2.5 than 5,8-diethyl the dodecane l6 2.3 4.0 present 5-ethyl-8- invenhexyl 24 0.69 2.3 tion hexadecane Squalane 30 O 0.33

Table 2 clearly shows that the synthetic higher hydrocarbons of the present invention had practically no stimulation of animal skin. This is the same as that of squalane. However, the fluid paraft'me and the comparative hydrocarbons having less than 26 carbon atoms had high stimulation of animal skins.

Since it was observed that the synthetic higher hydrocarbons of the present invention are harmless to animal skin, the harmlessness to human skin of the synthetic higher hydrocarbons usable for the present invention, was confirmed by the testing detailed below.

3. Irritation of Human Skin One hundred girls were subjected for testing the synthetic higher hydrocarbons of the present invention as shown in Table 2 and sequalane. The higher hydrocarbons were applied in an amount of 0.05 ml onto lint pieces. The lint pieces were put on the subjects fore arms or the inner aspects of their elbows covered by special adhesive tapes and secured by bandages. The test were continued for 48 hours. Observations were made after 24 hours and 48 hours, for erythemata, edemata, papules and blisters. With respect to all the tested hydrocarbons, no change was observed on any of the test portions of the subjects. The synthetic higher hydrocarbons of the present invention as shown in Table 2 were further subjected to tests which might indicate stimulation of the mucous membranes of the eyes involving the cornea, iris and conjunctive which were observed at predetermined intervals of time. Also tests were carried out to observe effect on human skin and effects of acute toxicity resulting from ingestion of doses of 25 ml/kg body weight. All the results of the tests were negative. That is, the excellent safety of the synthetic higher hydrocarbons of the present invention was confirmed.

4. Stability Against Bacterial Decomposition Five hydrocarbon compounds as shown in Table 3 were subjected to a test for stability against bacterial decomposition.

Two kinds of bacteria, Pseudomonas aeryuginosa and Pseudomonas Strain No. 23 (non-identified) were cultured in the culture media under the conditions detailed below.

1. Composition of culture medium 10 g hydrocarbon compound to be tested 2.5 g K2HPO4 0.5 g KH2PO4 0.3 g MgSO 0.3 g CaCI; 3.0 g (NH SO 0.3 g NaCl 1000 ml water 2. Culture condition 30 ml of culture medium was charged into a ml shaking flask sterilized in an autoclave at a high tem perature, and allowed to cool to room temperature. One platinum loop of the bacterial suspension was inoculated into the culture medium. The inoculated culture medium was shaken at a frequency of l20/minutes at a temperature of 30C for 7 days to culture the bacterium.

The multiplication of the bacterial fungus bodies was determined by the method detailed below.

tion in the bacterial fungus bodies. The higher the absorption, the larger the multiplication.

The degree of multiplication was expressed in terms of the references detailed below.

Great multiplication Normal multiplication Impossible to determine No multiplication For example, six kinds of hydrocarbon compounds were used instead of the hydrocarbons of the present invention and the multiplication was measured.

The results are shown in Table 3.

Table 3 Hydrocarbon Bacteria Number Pseudoof monas Examcarbon Pseudomonas strain ple Name atoms aeruginosa No. 23

Corn- Average parative Liquid paraffin 20 From Table 3., it was established that the higher satu rated branched hydrocarbon cour -rounds of the present invention have a higher stability against bacterial decomposition than that of the conventional fluid parai' fins, even when the synthetic higher hydrot arbons cosmetics containing the hydrocarbons are applied onto or sprinkled over human skin in atmosphere This indicates that the synthetic higher hydrocarbons of the present invention have a high ability to keep the perfume of the cosmetics for a prolonged time and thus, are highly valuable as the cosmetic base.

The synthetic higher hydrocarbons of the present invention can be utilized as a cosmetic base for the treat ment and make-up products, such as O/W type nutritious cream, W/O type nutritious cream. pomade. lip stick, bath oil, skin lotion, skin moisturizer. eye make up and body lotion The cosmetics are prepared by making the synthetic higher hydrocarbon with the other cosmetic ingredients. for example, cctylalcohol. vaseline, lanoiine, polyoxyethylcne cetylalcohol ether. polyethylene glycol. bees war-1 soibitan monoolealc,

polyoxyethylene sorbitan ntunoolcate, glycerol trioleo1" LZNiLAIVHiIU SW of yascilic, nctwinal tei also re- "petrulatunr and lir oi ii droit; lanolin urinperature of 50" to 60? Wlnlc stir ii i i-filltlktllldilfittl ferre-l was melted at ring Tilmel as emulsified in water containing 3" or poiyoxycfhjisixe cetylzllcohol or nol etlrylcne g coi. and thersmall ethcr and l t amounts of perfume and antiseptic v added into the sill emulsion ii tn tutietnine, :3 w

For comparison. the same procedures as stated above were repeated using squalane instead of 5-ethyl8-octyl octadecane.

The nutritious cream of the present example had cosmetic qualities similar to those of the comparison Cl'CLlr'T l.

EXAMPLE 2 A W/G type nutritious cream was prepared by the following procedures.

40% 9.12-dihexyl eicosane was mixed with l0% of bees wax and 10% of hydrous lanoline. The mixture was heated at a temperature of to C while stirring to form a uniform solution 36% of ion-exchanged water containing 3% of sorbitan monooleate and l% of polyoxyethylene sorbitan monooleate were emulsified into the solution. A small amount of perfume and antiseptic were added to the emulsion.

The resulting W/O type nutritious cream had excellent cosmetic properties.

EXAMPLE 3 a perfumev The mixture was molded in a lipstick mold. The lipstick thus formed was found to be satisfactory in cosmetic quality.

EXAMPLE 4 A pomade was prepared by the following method. 9% of 9.12-dihexyl eicosane was mixed with 52% of white vascline. 6% of solid paraffin and 30% of olive oil and the mixture was melted at a temperature of C while stirring. The melt was mixed with a necessary amount of coloring matter. The colored melt was allowed to cool to a temperature of 40 50C and mixed with 3% of a perfume and a necessary amount of an antioxidizing agent while stirring. The mixture was fed into a container and allowed to cool to room temperature.

The resulting pomade was found to be satisfactory in cosmetic quality.

EXAMPLE 5 A hath oil was prepared by the procedures detailed below.

50% of 2,2,4trimethyl- 1 0-ethyl-7( 1 ,3,3- irinicthylbutyl) tetradecane and 25% 0f 2,2,4,l3,l5,lhcxamethyl-7,l0-bis (l.3,3-trimethylbutyl)hexadecane were uniformly mixed with 15% of glycerol trioleate, 5% of polyoxyethylene oleyl alcohol ether and 5% of 2 perfume. The mixture was heated at 40 to 50C while stirring,

'The resultant bath oil was found to be satisfactory in its cosme ic quality,

l in a method of cosmetically treating human skin ilt.lrtlt. 'i'iisif=g application of a non-irritating cosmetic (,t =rnpt sition Comprising conventional cosmetic agents, i l." improvement which comprises employing as a nonirritating cosmetic base of said cosmetic composition at least one saturated, branched synthetic higher hydro- ;arbon having 26 48 carbon atoms and having the structural formula:

cncn CH2 ca wherein R R R and R, represent an alkyl radical of 2 to carbon atoms respectively, but R differs from R and R differs from R 2. The method of claim 1, wherein said saturated, branched higher hydrocarbon is selected from the group consisting of 2,2,4-trimethy1-l0-ethy1-7-(1,3,3,- trimethylbutyl)tetradecane, 5-ethy1-8-octyloctadecane, 2,2,4-trimethyl-7-( 1,3,3-trimethylbutyl- )eicosane, 9,12-dihexyl-eicosane, hexaethyl-eicosane, S-ethyl-S-decyl-eicosane, 2,2,4,l 3,15 l S-hexamethyl- 7,l0-bis( 1 ,3,3-trimethylbutyl)hexadecane, 9-hexyl 1 2- octyl-docosane, 2,2,4-trimethyl-7-(1,3,3- trimethylbutyl)- l O-octyl-eicosane, 1 1,14-dioctyltetracosane, 9-hexyl-l2-decyl-tetracosane, 2,2,4- trimethyl-7-( 1,3,3-trimethylbutyl l O-decyldocosane, ll-octy1-l4-decyl-hexacosane and 13,16-didecyloctacosane.

3. In a cosmetic composition comprising conventional cosmetic agents, the improvement which comprises employing as a non-irritating cosmetic base of said cosmetic composition at least one saturated,

branched synthetic higher hydrocarbon having 26 to 48 carbon atoms and having the structural formula;

\CHCH2 CH2 CH'

Claims (4)

1. IN A METHOD OF COSMETICALLY TREATING HUMAN SKIN COMPRISING APPLICATION OF A NON-IRRITATING COSMETIC COMPOSITION COMPRISING CONVENTIONAL COSMETIC AGENTS, THE IMPROVEMENT WHICH COMPRISES EMPLOYING AS A NON-IRRIATING COSMETID BASE OF SAID COSMETIC COMPOSITION AT LEAST ONE SATURATED, BRANCHED SYNTHETIC HIGHER HYDROCARBON HAVING 26-48 CARBON ATOMS AND HAVING THE STRUCTURAL FORMULA:
2. The method of claim 1, wherein said saturated, branched higher hydrocarbon is selected from the group consisting of 2,2, 4-trimethyl-10-ethyl-7-(1,3,3,-trimethylbutyl)tetradecane, 5-ethyl-8-octyl-octadecane, 2,2,4-trimethyl-7-(1,3,3-trimethylbutyl)eicosane, 9,12-dihexyl-eicosane, hexaethyl-eicosane, 5-ethyl-8-decyl-eicosane, 2,2,4,13,15,15-hexamethyl-7, 10-bis(1,3,3-trimethylbutyl)hexadecane, 9-hexyl-12-octyl-docosane, 2,2,4-trimethyl-7-(1,3,3-trimethylbutyl)-10-octyl-eicosane, 11,14-dioctyl-tetracosane, 9-hexyl-12-decyl-tetracosane, 2,2,4-trimethyl-7-(1,3,3-trimethylbutyl)-10-decyldocosane, 11-octyl-14-decyl-hexacosane and 13,16-didecyl-octacosane.
3. In a cosmetic composition comprising conventional cosmetic agents, the improvement which comprises employing as a non-irritating cosmetic base of said cosmetic composition at least one saturated, branched synthetic higher hydrocarbon having 26 to 48 carbon atoms and having the structural formula;
4. The cosmetic composition of claim 3, wherein said saturated, branched higher hydrocarbon is selected from the group consisting of 2,2,4-trimethyl-10-ethyl-7-(1,3,3-trimethylbutyl)tetradecane, 5-ethyl-8-octyl-octadecane, 2,2,4-trimethyl-7-(1,3,3,-trimethylbutyl) eicosane, 9,12-dihexyl-eicosane, hexaethyl-eicosane, 5-ethyl-8-decyleicosane, 2,2,4,13,15,15-hexamethyl-7, 10-bis (1,3,3,-trimethylbutyl) hexadecane, 9-hexyl-12-octyl-docosane, 2,2,4-trimethyl-7-(1,3,3,-trimethylbutyl)-10-octyl-eicosane, 11,14-dioctyl-tetracosane, 9-hexyL-12-decyl-tetracosane, 2,2,4-trimethyl-7-(1,3,3,-trimethylbutyl)-10-decyldocosane, 11-octyl-14-decyl-hexacosane and 13,16-didecyl-octacosane.
US3886287A 1972-10-06 1973-05-24 Cosmetics containing saturated, branched synthetic higher hydrocarbon Expired - Lifetime US3886287A (en)

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US4183917A (en) * 1976-12-25 1980-01-15 The Lion Dentifrice Co., Ltd. Emulsion-type hair conditioner composition
US4784843A (en) * 1985-03-01 1988-11-15 Basf Aktiengesellschaft Dicyclohexylalkanes, their preparation, cosmetic and pharmaceutical formulations containing these compounds, and their use as oil components
US20040202739A1 (en) * 2000-06-27 2004-10-14 Crosby Martin G. Compositions and methods for treating female sexual response
US20070238909A1 (en) * 2006-02-03 2007-10-11 Gadewar Sagar B Continuous process for converting natural gas to liquid hydrocarbons
US20080171898A1 (en) * 2004-04-16 2008-07-17 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US20080200740A1 (en) * 2004-04-16 2008-08-21 Marathon Oil Company Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US20090312586A1 (en) * 2008-06-13 2009-12-17 Marathon Gtf Technology, Ltd. Hydrogenation of multi-brominated alkanes
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
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US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US20110218372A1 (en) * 2010-03-02 2011-09-08 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
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US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
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US4368189A (en) * 1981-08-03 1983-01-11 Eli Lilly And Company Cosmetic moisturizer formulation
US4609545A (en) * 1982-11-24 1986-09-02 Schlossman Mitchell L Compressing aid for compressing powders
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US4183917A (en) * 1976-12-25 1980-01-15 The Lion Dentifrice Co., Ltd. Emulsion-type hair conditioner composition
US4784843A (en) * 1985-03-01 1988-11-15 Basf Aktiengesellschaft Dicyclohexylalkanes, their preparation, cosmetic and pharmaceutical formulations containing these compounds, and their use as oil components
US8128972B2 (en) 2000-06-27 2012-03-06 Semprae Laboratories, Inc. Compositions and methods for enhancing and treating female sexual response
US20040202739A1 (en) * 2000-06-27 2004-10-14 Crosby Martin G. Compositions and methods for treating female sexual response
US7875299B2 (en) * 2000-06-27 2011-01-25 Semprae Laboratories, Inc. Compositions and methods for enhancing or treating female sexual response
US8415512B2 (en) 2001-06-20 2013-04-09 Grt, Inc. Hydrocarbon conversion process improvements
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7560607B2 (en) 2004-04-16 2009-07-14 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20080200740A1 (en) * 2004-04-16 2008-08-21 Marathon Oil Company Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US20080171898A1 (en) * 2004-04-16 2008-07-17 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8232441B2 (en) 2004-04-16 2012-07-31 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US20080183022A1 (en) * 2004-04-16 2008-07-31 Waycuilis John J Process for converting gaseous alkanes to liquid hydrocarbons
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US20070238909A1 (en) * 2006-02-03 2007-10-11 Gadewar Sagar B Continuous process for converting natural gas to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US7579510B2 (en) 2006-02-03 2009-08-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
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US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US20090312586A1 (en) * 2008-06-13 2009-12-17 Marathon Gtf Technology, Ltd. Hydrogenation of multi-brominated alkanes
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US20110015458A1 (en) * 2009-07-15 2011-01-20 Marathon Gtf Technology, Ltd. Conversion of hydrogen bromide to elemental bromine
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US20110218372A1 (en) * 2010-03-02 2011-09-08 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
WO2017050943A1 (en) * 2015-09-22 2017-03-30 Biosynthis Branched saturated hydrocarbon cosmetic ingredient
FR3041254A1 (en) * 2015-09-22 2017-03-24 Biosynthis Cosmetic Ingredient has hydrocarbon saturated branched

Also Published As

Publication number Publication date Type
FR2201863A1 (en) 1974-05-03 application
DE2327087C3 (en) 1975-08-28 grant
DE2327087A1 (en) 1974-04-25 application
JPS4955853A (en) 1974-05-30 application
DE2327087B2 (en) 1975-01-16 application
FR2201863B1 (en) 1977-05-06 grant
JPS5231022B2 (en) 1977-08-12 grant
GB1379013A (en) 1975-01-02 application

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