DE2316999A1 - Means of stimulating the cold receptors of the human nervous system and their use - Google Patents

Description

received nm

Dr. Hans-Heinrich Willrath

Ur. Dieter Weber Diploma in Phys. Klaus Seifiert

PATENT LAWYERS

_{D 62 WIF} c _{RÄnFN on}

~ WIESBADEN June 20th

p ° stfa * 1327

Gustav-Freytag-Stra6e 25

* p «« h 372720

Il / sch

Group V

Wilkinson Sword Limited, Sword Works,

Southfield Road, London ¥. k _t

Great Britain

Means with a stimulating effect on the cold receptors of the human nervous system and their Ver * ending

Priority : UK Patent Application No. 17 913/72 dated April 18, 1972

The invention relates to ingestible, topical and other compositions having a physiological cooling effect

ORIGINAL INSPECTED

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Postal check: Frankfurt / Main 6763 Bank: Dresdner Bank AG, Wiesbaden, Kottto no. S76 807

.- ..:. 2316993

on the skin and on the mucous membranes of the body, especially the mucous membranes of the nose and the airways.

Menthol is known and used extensively for its physiological cooling effect on the skin and mucous membranes of the mouth Scope as a flavor (menthol is a major ingredient of peppermint oil) in food, beverages, tooth-training products, Mouthwashes, etc., and used as an ingredient in a wide variety of toiletries, ointments and lotions for topical application. 'Menthol is also known as a tobacco additive to create a cool sensation in the mouth when smoking.

It is known that the cooling effect of menthol is physiological Effect as a result of the direct action of menthol on the nerve ends of the human body is what is responsible for the Perception of hot or cold are responsible, and that the cooling effect does not affect any latent heat of vaporization. It is believed that menthol acts as a direct stimulant on the cold receptors at the nerve endings, which in turn "acts" Stimulate the central nervous system.

Although menthol is well known as a physiological coolant, is in some compositions, its use by its strong peppery odor limited.

Certain acyclic alcohols with a structure similar to that of menthol, such as' 2, 4,6 * -trimethyl ~ 4-heptanol, have according to information in the literature, it is also a physiological one Cooling effect combined with a peppermint-like smell that of menthol, see Parfuias-Cosirietiques-Savons, May 1956, Pages 17 to 20..

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The present invention is based on the discovery that certain other alcohols which can easily be synthesized have a physiological cooling effect similar to that obtained with menthol, but not the strong odor property of menthol. Indeed, in many cases the compounds have a pleasant fruity odor. Such compounds are therefore used as odorous substances or perfuming agents in a wide range of more ingestible ways and topical compositions. More specifically, they find use as ingredients in compositions for the Use in the nose, for vaporizing liniments and for ointments.

The compounds having a physiological cooling effect to be used in the present invention are secondary and tertiary alkanols of the general formula

R ₀ -C-OH
^R 3

wherein R is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R _{2 is} an alkyl group having 2 to 5 carbon atoms and R 1 is an alkyl group having 2 to 5 carbon atoms, where, when R is a hydrogen atom, at least one of the groups R ₂ and R _{3 are} a branched-chain group when R 1 is a methyl group and one of the groups R ₂ and R _{3 is} an isobutyl group and the other of the two groups R ₂ and R _{3 is} one

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Kthyl, n-propyl, isopropyl, η-butyl, sec-butyl, tert-butyl or a straight-chain or branched-chain amyl group and where R ₁ , R ₀ and R ^ together contain a total of 7 to 10 carbon atoms.

Thus, according to the present invention, one obtains an article or an agent capable of stimulating the cold receptors of the nervous system of the human body, and these articles or means consist of a cold receptor stimulant and.a carrier or vehicle therefor, the said Stimulant comprises a secondary or tertiary alkanol of the above formula.

Among the preferred compounds which are used in accordance with the present invention are secondary alkanols of the above formula, ie where R _{1 is} a hydrogen atom containing 7 to 9 carbon atoms which _{are shared between R 2} and Ro, at least one of the Groups R ₇ and R ₀ ″ in the d- or ß-position to the carbon atom shown in the formula has a branch, as well as tertiary alkanols of the above formula in which R, a methyl, ethyl or propyl group and R 1, R ₀ and R ^ together have 8 to 10 carbon atoms, and most preferably at least one of the groups R ₂ and R _{3 has} a branch in the d- or β-position.

Typical alkanols that fall under the above formula and which in the compositions according to the present invention

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are listed in the following table, where their relative activities as a stimulant for the cold receptors of the human nervous system are given. The bigger the The number of stars indicated is / the greater the activity, i.e. the greater the cooling effect of a certain amount of Link.

Tabel Activity smell

woody

camphor-like

fighter-eucalyptus-like

earthy-crab-like

earthy-carapfer-like

fruity

fruity camp-eucalyptus-like.

earthy

Linalool-geraniol-like

eucalyptus-camphor-like

earthy-fruity kai-tip like

eucalyptus geranium-like

C ₀ K, - XSO-C ₀ H-, CH (CH ₀ ) CH ₉ CH ₀ ++++ earthy-kaiapferar-

ο 3 7 i ζ λ _tig

^R l R ₂ ' ^R 3 2 ^CH 3 HC ₃ H ₇ nC ₃ H ₇ ' XSO-C ₃ H ₇ ) ₂ HC ₃ H ₇ ■ XSO-C ₃ H ₇ XSO-C ₃ H ₇ ) ₂ ^C 2 ^H 5 C ₂ H ₅ CH (CH ₃ ) CK ) ₂ CH ₃ UC ₃ H ₇ . CH ₂ CH (CH ₃ CV
2 ^UK 3 H HC ₃ H ₇ CII ₂ CH (CH ₃ ) ₂ H XSO-C ₃ H ₇ CH ₂ CH (CH ₃ H . XSO-C ₃ H ₇ CH (CH ₃ ) CH ₂ CH ₃ H CH ₀ CH (CHo) ₀ CH ₂ CH (CH ₃ C ₂ H ₅ XSO-C ₃ H ₇ XSO-C ₀ H ₇ cn ₃ CH ₂ CH (CH ₃ J ₂ CH (CH ₃ ) CH XSo-C ₃ H ₇ XSO-C ₃ H ₇ XSO-C ₃ H ₇

HC ₃ H ₇ nC _o H ^ ' Ti-CJl _n ++++ woody

CH ₀ nC-vH ^ - CH ₉ C (CK ₀ ) _o ++++ earthy-camphor-

j 7. ζ 0 5 _ti g.

IT nC H CH (CF ₀ ) CiI ₉ CH ₀ +++ fruity-kaioDfer-

^. & λ- like

H XSo-C ₃ H ₇ CH ₂ CH ₂ CH ₂ CH ₃ . +++ fruity

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HC ₃ H ₇ -G- 2316999 CK ₃ HC ₃ H ₇ C (CH ₃ ) ₃ - f - ++ kampfer-euka-
lyptus-like CH ₃ CH (CH ₃ ) CH ₇ CH ₃ CH ₉ CH-CH (CHo) ₀ 1 - ++ fruity-earthy CH ₃ * HC ₃ H ₇ C (CH ₃ J ₂ CH ₂ CH ₃ n- + caramel-like-
fruity-kamp
ferlike CH ₃ C ₂ H ₅ w ■ · ■ C ^ T-? -J
XX v ^ i ^ il ^ 1 H + earthy-woody
fruity CH ₃ HC ₃ H ₇ C (CH ₃ J ₃ H l + kampfer-euka-
lyptus-like CK ₃ ^C 2 ^H 5 ISO-C ₃ H ₇ ^ (- + kampfer-euka-
lyptus-like H - HC ₃ H ₇ CH (CH ₃ ) CH ₂ CH ₂ CH ₃ H l + flowery-fruity H HC ₃ H ₇ C (CH ₃ ) ₃ ^ f- + pineapple-like-
camphor-like H nC ₃ H ₇ CH ₂ CH ₂ CH (CH ₃ ) ₂ H - + fruity (ana
nasal) CH ₃ ^C 2 ^H 5 CH ₂ CK ₂ CH ₂ CH ₂ CH ₃ ^ fruity CH ₃ ^C 2 ^H 5 CH ₂ CH ₂ CH ₂ CH ₃ Λ fruity H- / ~ ιττ ^ ¹ TU / ~ <ΐΤ fi ~ * TJ \ Λ fruity (ana
nasal)

When the compounds that are used according to the invention, have an asymmetric carbon atom can be any optical Isomer can be used in its pure form, but a mixture of optical isomers is generally used. In some cases there may be a difference in the cooling effect between the optical isomers exist, and in such cases one or other isomeric form may be preferred.

The compounds of the invention are useful in a large number A variety of compositions for ingestion or application to the human body. Generally speaking These compositions can be in ingestible jund topically Applicable compositions can be subdivided, using both terms can be applied in the broadest sense. So they close

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Eir.nehrfDaran not only include foods and beverages that are ingested and swallowed by the dog, but also other orally ingested compositions that are taken for reasons other than their nutritional value, such as Mag Stimulant tablets, antacids, laxatives, etc. Edible or ingestible compositions are also intended to include those edible compositions which are ingested by the mouth but not necessarily swallowed, such as chewing gum, topical compositions are not only such as perfumes, powders and others Toilet preparations, lotions, ointments, oils and creams that are applied to the outer surface of the human body for medicinal or other purposes, but also compositions that are applied to the internal mucous membranes of the body or, in normal use, in contact with these corks , as with the mucous membranes de r nose, mouth or throat, whether by direct or indirect application or inhalation, so that this term includes cheese and throat sprays, cream cleansers, mouthwashes and gargle preparations. Thoughts also fall within the scope of the invention. Toilet articles or toilet articles, such as cleaning tissues and toothpicks, which are used with the active cooling. Connection impregnated or coated.

Bir.e another class of compositions found within the Invention credits are tobacco and related objects, like pipe and cigarette filters, especially filter mouthpieces and filter tips for cigarettes.

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-S- ■ - ■ ■ ■

The compositions according to the invention contain one amount the active cooling compound, which is sufficient to activate the cold receptors in the areas of the skin or mucous membrane those in contact with the compositions and thereby evoke the desired sensation of cold. Since the Degree and length of cooling sensation from connection to connection is different, the amount of stimulant used in each composition also varies widely. As a guideline it can be said that with the more active compounds, a strong feeling of cooling when applied to the skin of so little v / ie 0.05 ml of a 1 2; solution of the active ingredient in Ethanol is produced. Achieved in the less active compounds a strong feeling of coolness can only be achieved with more concentrated Solutions, such as with 5% by weight or more of the active ingredient. It must also be admitted that such Skin tests are somewhat subjective, with individual test subjects have a greater or lesser cooling sensation than others ", if they are subjected to the same test .. · ■

In the formulations of the compositions or agents according to the In accordance with the invention, the active cooling compound is usually incorporated into a carrier which may or may not be completely inert consist of or contain other active ingredients can. A wide variety of carriers are suitable, depending on the end use of the agent, such as "carriers in the form of solids, liquids, emulsions, foams or gels. Typical carriers for the active cooling compounds are aqueous or alcoholic solutions, oils and fats, such as

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Hydrocarbon oils, fatty acid esters, long-chain alcohols and silicone oils, finely divided solids such as starch or talc, Cellulose materials such as tissue paper, tobacco, low boiling points Hydrocarbons and halogenated hydrocarbons known as Aerosol propellants are used, gums and natural or synthetic resins. . ·

In most of the compositions according to the invention, the Carriers contain one or more of the following agents or contain as additives: Antacids, antiseptic or analgesic substances Substances, flavorings, colorings or odorants or surface-active substances. -.

The following explanations explain the range of compositions can be incorporated into the active cooling compounds according to the invention:

1. Edible or potable compositions such as alcoholic and non-alcoholic beverages, confectionery, chewing gum, cachpus, ice cream, jellies. '■

2. Toilet articles or preparations, such as post-shave lotions, shaving soaps, shaving creams and shaving foam, toilet water, deodorants and antiperspirants, "solid eau de cologne", toilet soaps, bath oils and bath salts, shampoons, hair oils, talcum powder, face creams, hand lotions, face creams, hand lotions, Dentifrices, toothpicks, mouthwash, caartonics and eye drops.

3.Radicaments, such as antiseptic ointments, hair ointments, creams, Lotions, anti-congestion agents, anti-irritant "ittol", cough loops, pcichan lozenges, antacids and

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- ι ο -

Preparations for upset stomach and oral analgesics. '-

4. Tobacco preparations such as cigars, cigarettes, pipe tobacco, chewing tobacco and snuff, tobacco filters, especially filter mouthpieces, Filter tips for cigarettes.

5. Different preparations such as water-soluble adhesive compositions for envelopes, postage stamps, adhesive labels, etc., ■. ·.

Special preparations according to the invention are hereinafter in individual discussed.

Edible and potable compositions

The edible and potable compositions of the invention contain the active cooling compound in combination with an edible carrier and usually a dish-improving or coloring agent. The special effect of the cooling connections is that of a cool or fresh sensation in the. _: Dog and, in some cases, self-made in the stomach, and therefore the compounds are particularly useful in sugar-based confections such as chocolate, boiled candies, and sugar-based confections; werk, in ice cream and jellies, and in chewing gum »Such confectionery is made by conventional methods and recipes and as such does not form part of the invention. The active compound is added to the recipe at a convenient point and in an amount sufficient to prevent the to produce the desired cooling effect in the end product. As stated earlier, the amount will vary depending on the particular compound being used. Degree of the desired cooling effect: and the strength of other gas

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pollutants in the recipe. As a general guideline, lets say, however, that they are in the range from 0.1 to 5.0% by weight, based on the Gesarritsusainiriensosition, to be suitable proven.

Similar considerations also apply to the composition of Drinks. Generally speaking, the compounds are mostly found in "soft drinks" such as fruit juices, lemonade, cola, etc. used, but they can also be used in alcoholic. Drinks are used. The amount of the compound used is general in the range from 0.05 to 2.5% by weight, based on the total composition. '

Toilet articles and preparations or means

The main usefulness is because of the cooling sensation on the skin the cooling compounds according to the invention in the wide Toilet preparations and toilet articles; The specific preparations discussed below are only grounded given by way of example. ,

A greater usefulness is in the field of post-shave lotions, Toilet water etc. in which the compounds in alcoholic or aqueous-alcoholic solution are used ", such solutions usually containing a perfume or a mild antiseptic or both. The added Amounts of the compounds are generally in the range from 0.1 to 10% by weight, based on the weight of the total composition.

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Another area of friability is that of soaps, shampoons, 3adeöla , etc., where the compound is used in combination with an oil or fat or a natural or synthetic surface-active agent, such as a fatty acid salt or a lauroyl sulfate salt, the composition usually also being an essential oil or contains perfume. The range of soap compositions includes soaps of all kinds such as toilet soaps, shaving soaps, shaving foam, etc. Usually the compound is added to compositions in an amount of 1.0 to 10% by weight. Another class of toilet preparations into which compounds according to the invention can be incorporated are, for example, cosmetic creams and emollients, such as those which are usually based on emulsions and optionally contain a number of ingredients such as waxes, protective agents _r perfumes, antiseptics ,. Ads agents, pigments, etc. Within this class there are also lipstick compositions, tongues, such as compositions, which usually contain an oil and wax base, in which compounds according to the invention together with the conventional ingredients such as pigments, perfumes, etc. ., can be incorporated. Again, the formulation of such preparations is disregarded. from the incorporation of the cooling compound, conventional, wherein the cooling compound is usually incorporated in an amount of ö _r ö5 to 10.0% by weight.

Oral hygiene preparations containing the cooling compounds included are, for example, mouthwashes. Gargles and Tooth cleaning aids. The first two can be viewed together

303846/1188

- IJ - -

be treated and usually include an aqueous, alcoholic or aqueous-alcoholic solution of an antiseptic, which is often colored or to produce a better taste is provided with flavorings, and to these the Cooling agent in an amount of 0.01 to 10.0% by weight is added.

Dentifrices can be in the form of solid blocks, powders, pastes or liquids and usually include one fine-grained grinding or polishing material, such as precipitated chalk, Silica, magnesium silicate, aluminum hydroxide, or other similar materials known in the art, as well a detergent or foaming agent. Optional-used Components that can also be incorporated are flavorings and dyes, antiseptics, lubricants, "thickeners, emulsifiers or plasticizers · The amount the cooling compounds that are added to such preparations are generally in the range from 0.1 to 5.0% by weight, · based on the weight of the total composition.

Medication '

Because of its cooling effect on the skin and on the mucous membranes in the mouth, throat, and nose and gastrointestinal tract can the cooling compounds according to the invention in different oral medicines, rabbit and throat sprays and topical preparations can be used, especially where an anti-irritant effect is required is. Specifically, the coolants can be found in antacids and

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. "Acrens disorder preventive agents are incorporated", especially in those based on: T at riuribi carbon afc. Magnesium oxide, calcium or magnesium carbonates, aluminum or magnesium hydroxide or magnasium trisilicate. In such preparations is the coolant is usually added in an amount of from 0.01 to 2.0% by weight.

The cooling compounds can also be administered orally analgesic compositions such as with acetylsalicylic acid or their salts, are incorporated »

Because of their volatility and their effect on the mucous membranes the nose and airways are those of the present invention The compounds used are particularly useful for nasal wrinkles to prevent blood rush, as in combination with Ephedrine, as well as in throat lozenges and vaporizing rubs; agents and agents that contain an oily base, in which the cooling agent in amounts of 1.0 to 10% by weight can be incorporated »■

Tobacco Preparations ". -."■; .-

The cooling agents according to the invention can also be used directly in Tobacco can be incorporated in order to produce a cooling effect when smoking, but without the strong and characteristic odor, associated with tobacco and cigarettes, -which "with menthol are offset. An even more beneficial use of the cooling Means according to the invention is that in pipe or sigarette filters, especially in cigarettes with a filter mouthpiece. The filter material pad, which can be of any known type,

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% 'ie from cellulose acetate, paper, cotton, cv cellulose, or asbestos fibers, is simply an alcoholic Solution of the cooling agent is impregnated and is then dried, whereby the cooling agent is in the filter pad precipitates. The effect is a pleasantly cool sensation in the mouth when the cigarette is smoked. As little as 0.1 rag of the coolant is effective.

The following examples illustrate objects and means according to the invention explained.

Example 1 . ·.

After-shave lotion

A post-shave lotion was made according to the following recipe, by dissolving the constituents of the liquid, followed by cooling and filtering. ·

Denatured ethanol. 75%

Diethyl phthalate 1.0%

Propylene glycol 1, 0%

Lactic acid ■ 1.0%

Perfume . . . 3.0%

Water ^{£ uf} 100%

3% by weight, based on the total composition, were added to the base lotion incorporated into 3-ethyl-4-raethyl-3-hexanol.

was v _snn a.ie finished lotion on the face applied a clearly identifiable cooling effect after a short since been perceived.

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-O

I2eis: iel 2

Aggen Lotion

An eye lotion was made from the following ingredients:: ... ■ · '

Saubernut · - · -.- "12.95%

Boric acid 2.00%

Sodium borate 0.5O%

Allantoin. 'O, O5%

Salicylic acid. 0.025%

Chlorobutol ■ O, O2% '

Zinc sulfate 0.004% ■

Water - ■ to 100%

For this composition, 0.15%, based on the total composition, an. ^ - Methyl-S-isopropyl-S-hexanol added. When used for bathing the eyes occurred on the ball of the eye and on the Eyelids a fresh sensation. . ■

Example 3

Toothpaste ■, ■

The following ingredients were mixed together in a mixer blended:

Dicalcium phosphate dihydrate ^; .40%

Sodium Lauryl Sarcosinate 1.5%

Glycerin. 30%

"Tatriuiacarboxymethy! Cellulose 1.5%

Saccharine sodium 0.2 %

Mätriui tibenzoate 0.2%

Wet 26.6%

1198

Shortly before the end of the mixing, 1/5% by weight -: - l3opro? yl-4-heptanql added to the mixer.

When used as a toothpaste, there was a cooling effect in the mouth established.

Example 4

corpse candy

! ■ Barrels were added to powdered sugar at 40 ° C to form a stiff paste. 1% 4-n-propyl-4-heptanol was then in the paste was stirred in, "and the mixture was allowed to set. You got a soft, sweet mass with a cooling effect in the mouth as with Peppermint, but without the peppermint-like taste or Odor.

Example 5 Cigarette tobacco

Hin cigarette tobacco was _{impregnated with 2/} 4-dimethyl-3-ethyl-3-pentane-pi and rolled into cigarettes, each of which contained about 0.001 g of the active compound. Smoking the impregnated cigarettes resulted in a cooling effect in the mouth, which is typical for cigarettes with menthol.

A similar effect can be seen when using a filter cigarette smokes in which the coolant was used to impregnate the filter mouthpiece instead of the tobacco.

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Example 6 ■ "

Antiseptic ointment

ZiriQ ointment was made according to the following recipe; manufactured:

Cetyltrimatylammonium bromide 4.0%

Cety! Alcohol. ■ 6.0%

Stearyl alcohol 6.0%

White 'paraffin' 14.0%

Mineral oil 21.0%

Water "to 100%

The ingredients were mixed together, heated to 60 ° C. warms and emulsifies in a mixer at high speed. To the mixture was added 4% 2,4-dimethyl-4-heptanol while mixing added.

When applied to the skin, the finished ointment gave a noticeable cooling effect. . '

Example, 7 ". '·

Aerosol shaving soap ""

Its aerosol shaving soap composition was made as follows Compiled recipe:.

Stearic acid 6.3%

; Lauric acid 2.7%

Triethanolamine ° 4.6%

sodium carboxymethyl cellulose 0.1 %

. Sorbitol 5 _f O%

y ^ sser to 100 %

Fragrance 0 _r 5%

. ■ "'309846/1198

The composition was prepared in such a way that the acid was combined in water, before the triethanolamine was added, the appliance was cooled and the other ingredients were added. 2% 2-mathyl-4-heptanol was then added to this equipment. The composition was then packaged in an aerosol container under pressure of a butane propellant. ■

When used when shaving. Was a fresh one on the face cool feeling strongly noticeable. - '.

Example 8

Toilet water . ·

A toilet water was made according to the following recipe:

Denatured ethanol 75.0%

a. ■

Perfume 5.0%

Water to 100%

For this recipe, 4.0%, based on the total composition, of 2,5-dimethyl-3-hexanol added.

As with the post-shave lotion, there was a cooling effect on the skin clearly recognizable, long after the cooling effect has ended, which could be attributable to the evaporation of the alcoholic vehicle.

Example 9
Deodorant

A deodorant that is available for delivery as an aerosol under pressure

-en
A suitable propellant was suitable as follows

manufactured:

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Denatured ethanol '96.9%

Hexachlorophene 2.0%

Isopropyl myristate 1.0%

Perfume 0.1%

Su this composition were 4% by weight "2 _r 6-dimethyl-4- heptanol added to the application of the final composition showed a significant cooling effect on the skin.

Example 10 _:

Hair shampoo '. .

10 g of sodium lauryl ether sulfate were in 9O g of water in a Mill dispersed at high speed. 4.5% by weight of 2,4-dimethyl-4-heptanol were added to this dispersion. If the hair has been washed using this shampoo, put a "fresh, cool sensation on the scalp fixed. . .-- "··" · "-

Example 11 ---- * '-

Solid cologne · - "'.

A solid Cologne water was made according to the following. Recipe made:

Denatured ethanol "" 74.5%

Propylene glycol '■. 3.0%

Sodium stearate. . 5.0%

Perfume ■ 5.0%

Water to 100%

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Os' Tütriuinstearafc was dissolved in a warm mixture of ethanol, pronylene glycol and water by stirring. The perfume and 4.0 % 2,4-dimethyl-S-isopropyl-3-pentanol were added to this solution and the mixture was allowed to solidify into a waxy cake.

When applied to the face, a pronounced chill effect was noticeable.

Example 12 Mouthwash

A concentrated mouthwash preparation was made according to the following recipe manufactured:

Ethanol 3.0%

3orax. 2.0%

iTetrium bicarbonate. 1.0%

Glycerine 10.0%

Flavor 0.4%

Thymol 0.03%

Water to 100%

To this composition was dimethyl-3-'äthyl-3-pentanol were added 0.2% _2/4 ~. When diluted with about ten times the volume of water and used to rinse the mouth, a cooling effect was obtained in the mouth.

Example 13 Non-alcoholic drink

I'in concentrate of a soft drink was prepared according to the following recipe t

3093A6 / 1198

2316999 % 60 ίο %. O , 2 % O , 1 % 0 , 2% ·. traces to 100

Roin orange juice

Sucrose

Saccharin

Orange flavor

citric acid

Sulfur dioxide

water

0.1% 4 ~ isopropyl-4-heptanol was added to the concentrate. The concentrate is diluted with water and tried. An orange taste with a pleasantly cool aftertaste was found. . '· ■■■ · - ■ - "■" ·.

Example 14 Boiled candies

99/5% sucrose and Q, 5% citric acid were fused together extensively in the presence of a trace of water. ⁱ mixed in heptane oil. The melt was then poured / I-ian obtained boiled candies with a strong cooling effect in the mouth

Example 15

The oil-beneficial constituents match with one another:

MäfftesiuinearbOnat. ■ 41 _f 5%

Sorbitol <■ 49 _f 4 i

Sacöhärih. Ö / 1%

Talc. ■ I, Ö t

The dissoin mixture was 0.1% 4-n-ProOyl-4-heptanol during the dissolution added. After mixing, the gene volume was compressed into tablets of 0.5 g.

? 7enn nan took the tablets obtained in this way in his mouth and sucked, After a short time you noticed a noticeable cooling effect in the Stomach.-

Example 16 '·. ·

Cleaning fabric

A cleaning liquid was made according to the following recipe manufactured:

Triethanolamine Lauryl Sulphate 1.0%

Glycerine "- 2.0%

Perfume 0.95%

Water ' . to 100%

4% 4-isopropyl-4-heptanol was added to this liquid. A paper towel was then soaked in the liquid.

If the impregnated cloth has been used to wipe the skin, After a short period of time there was a fresh, cool feeling on the skin. · '

Example 17 Hydrophilic ointment

Its hydrophilic ointment was made according to the following recipe: ■

Propylene glycol 12%

l-octadecane oil ". 25%

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2316999 ο.
■ £> 25th s- ■ . ϊ % - - to 100

White 'soft paraffin

JTatriunlaurol sulfate

»" Ater ·

The atrium lauryl sulfate was added to the water and on 60 ° C heated. The paraffin was melted by heating to 60 ° C and then added to the sodium laurylsuif afc * - mixture added. Then Propylenglv were to this mixture col and 1-octadecanol added.

3% 3-ethyl-4-methyl-3-hexanol was added to the resulting mixture. When applied to the skin, the finished ointment gave a noticeable stinging effect- "." -. '

Example 18 . . . - ..

Evaporating Sinrei-bemlttel - '

4% 2,4-dimethyl-3-ethyl-3-peiiii: anol were mixed into 95% white paraffin. When rubbing into the skin, steam was released / the ajigenehia cooled "." -

Example 10 . ,. ',.

n ©. Ointment was aiaeh the folqeBdeu p

Diethyl salicylate 25

■ on

-elies ^ he ^ usamiffieBsefeziUög 'became; » 4% 2- ^

Skin burned-eight A-mräe-t w & xäe nrnZh fcurz ^ r soap & lm stronger

309 * 46 / 1-1-98-

The above examples illustrate the range of compounds and

-en
Composition within the scope of the invention. You serve

but not the limitation of the inventive concept.

Other compounds within the general formula are in
Equally suitable for use in compositions according to Examples 1 to 19, and the physiological cooling effect obtained with the compounds according to the invention allows the use of these compounds in a wide range of other agents and compositions where a cooling effect is of value
is.

309846/1198

Claims (4)

- 26 rinopgnnqfin nm tU -% * ■■; ■ "" - patent claims! 1.) Means with the receptors of the human nervous system stimulating effect with a content of an effective amount of a cold receptor stimulant, characterized in, that the cold receptor stimulant is a secondary or tertiary alkanol of the formula R ₉ -C-OH ι. R ₃ is wherein R _{1 is} a hydrogen atom or an alkyl group with up to 5 carbon atoms, R _{2 is} an alkyl group with 2 to 5 carbon atoms and R- is an alkyl group with 2 to 5 carbon atoms, where, when R _{1 is} a hydrogen atom, at least one of the groups R_ and R "denotes a branched-chain group and, when R _{1 is} a methyl group and one of the groups R- and R- is an isobutyl group, the other of the two groups R ₂ and R. is ethyl, n-propyl, isopropyl -, η-butyl, sec-butyl, tert-butyl or straight-chain or branched-chain amyl group and where R ₁ , R ₂ and R "together contain a total of J to 10 carbon atoms. 2.) Means according to claim 1, characterized in that the Kaltrezeptorstieulans has the above formula, wherein R _{1 is} a What β he st off atom, R ₂ and R together have 7 to carbon atoms and at least one of the groups 309846/1198 received nra R and R "has a branch in a CC or ß-position with respect to the carbon atom shown in the formula" 3.) Means according to claim 1 and 2, characterized in that the cold receptor stimulant has the above formula, wherein R _{1 is} a methyl, ethyl or propyl group and R ₁ , R _? and R "together have a total of 8 to 10 carbon atoms · 4.) Use of an agent according to claim 1 to 3 for Impregnation or coating of toilet articles. 309846711: 98