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WO1996028133A1 - Composition refrigerante - Google Patents

Composition refrigerante Download PDF

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Publication number
WO1996028133A1
WO1996028133A1 PCT/US1996/002257 US9602257W WO9628133A1 WO 1996028133 A1 WO1996028133 A1 WO 1996028133A1 US 9602257 W US9602257 W US 9602257W WO 9628133 A1 WO9628133 A1 WO 9628133A1
Authority
WO
WIPO (PCT)
Prior art keywords
compositions
composition according
composition
coolant
glycol
Prior art date
Application number
PCT/US1996/002257
Other languages
English (en)
Inventor
Deanna Kimberly Furman
Karen Ann Bell
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP96905554A priority Critical patent/EP0814751A1/fr
Priority to AU49285/96A priority patent/AU4928596A/en
Priority to MX9706958A priority patent/MX9706958A/es
Priority to JP8527604A priority patent/JPH11502195A/ja
Publication of WO1996028133A1 publication Critical patent/WO1996028133A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • compositions of various types have incorporated within them components which provide cooling sensation to mucosal membranes and/or to skin.
  • Such compositions include toothpastes, mouthwashes, perfumes, lotions, shaving cream, post shaving preparations, shampoos, antiperspirants, deodorants, beverages, chewing gum, tobacco products, and pharmaceutical products among many others.
  • menthol is a physiological effect due to the direct action of menthol on the nerve endings of the human body responsible for the detection of hot or cold and is not due to latent heat of evaporation. It is believed that the menthol acts as a direct stimulus on the cold receptors at the nerve endings which in turn stimulate the central nervous system.
  • menthol is well established as a physiological coolant, its use alone, in some compositions, is limited by its strong minty odor and its relative volatility.
  • N,N-Dimethyl 2- ethylbutanamide is reported as having a minty odor and refreshing effect, and the minty odor of N,N-diethyl 2,2-dimethylpropanamide is referred to.
  • a similar effect is reported for N,N-diethyl 2-ethylbutanamide in Berichte 39, 1223, (1906).
  • a minty odor has also been reported for 2,4,6- trimethylheptan-4-ol and 2,4,6-trimethyl hept-2-en- -ol in perfumes- Cosmetiqu ⁇ s-Svon, May 1956, pp. 17-20.
  • Carboxamides have also been disclosed for use in a variety of compositions. Two patents describing such materials and compositions are U.S. 4,136,163, January 23, 1979 to Watson, et al. and U.S. 4,230,688, October 28, 1980 to Rowsell, et al. These patents as well as those set forth above are incorporated herein in their entirety by reference.
  • It is a further object to provide improved coolant compositions comprising a glycol and a coolant wherein the pH is greater than about 8.2.
  • the present invention includes compositions comprising a suitable carrier, a glycol, and a coolant wherein the pH of said compositions is greater than about 8.2. Methods of providing cooling are also included within the scope of this invention.
  • glycol in this application is meant to include any glycol which is suitable for use on the skin, mucosal surfaces such as in the oral cavity or ingested. Suitable glycols include propylene glycol, butylene glycol, hexylene glycol and mixtures thereof, among others. The preferred glycol is propylene glycol.
  • glycol materials when used alone or in combination, are present at a level in the composition of from about 0.1% to about 10%, preferably from about 1 % to about 8%, most preferably from about 2% to about 6%.
  • the second required component of the present invention is a coolant.
  • the coolant can be any of a wide variety of materials. Included among such materials are carboxamides.
  • the carboxamides in the '163 patent are N-substituted-p-menthane- 3-carboxamides. These compounds are 3-substituted-p-menthanes of the formula:
  • R' when taken separately, is hydrogen or an aliphatic radical containing up to 25 carbon atoms; R" when taken separately is hydroxy, or an aliphatic radical containing up to 25 carbon atoms, with the proviso that when R' is hydrogen R" may also be an aryl radical of up to 10 carbon atoms and selected from the group consisting of substituted phenyl, phenalkyl or substituted phenalkyl, naphthyl and substituted naphthyl, pyridyl; and R' and R", when taken together with the nitrogen atom to which they are attached, represent a cyclic or heterocyclic group of up to 25 carbon atoms, e.g., piperidino, morpholino, etc.
  • aliphatic is intended to include any straight- chained, branched-chained or cyclic radical free or aromatic unsaturation, and thus embraces alky!, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyalkyl, acyloxyalkyl, alkoxy, alkoxyalkyl, aminoalkyl, acylaminoalkyl, carboxyalkyl and similar combinations.
  • R' and R" when aliphatic are methyl, ethyl, propyl, butyl, isobutyl, n-decyl, cyclopropyl, cyclohexyl, cyclopentyl, cycloheptylmethyl, 2-hydroxyethyl, 3-hydroxy-n-propyl, 6-hydroxy-n-hexyl, 2-aminoethyl, 2-acetoxyethyl, 2-ethylcarboxy ethyl, 4-hydroxybut-2-ynyl, carboxymethyl etc.
  • R" is aryl
  • typical values are benzyl, naphthyl, 4-methoxy- phenyl, 4-hydroxyphenyl, 4-methyl ⁇ henyl, 3-hydroxy-4-methylphenyl, 4- fluorophenyl, 4-nitrophenyl, 2-hydroxynaphthyl, pyridyl, etc.
  • the carboxamides of the '688 patent are certain acyclic tertiary and secondary carboxamides. These have the structure
  • R 3 where R' and R", when taken separately, are each hydrogen, C-1-C5 alkyl or C-j-C ⁇ hydroxyalkyl and provide a total of no more than 8 carbon atoms, with the proviso that when R' is hydrogen R" may also be alkylcarboxyalkyl of up to 6 carbon atoms;
  • R' and R" when taken together, represent an alkylene group of up to 6 carbon atoms, the opposite ends of which group are attached to the amide nitrogen atom thereby to form a nitrogen heterocycle, the carbon chain of which may optionally be interrupted by oxygen;
  • R-* is hydrogen or C1-C5 alkyl; and R2 and R3 are each C1-C5 alkyl; with the provisos that (i) R-* , R2 and R3 together provide a total of at least 5 carbon atoms, preferably from 5-10 carbon atoms; and (ii) when R*
  • Additional coolants include such materials as ketals, menthol, and diols. Preferred ketals for use in the present invention have the formula
  • R 1 represents a C*]-C ⁇ -alkylene radical having at least 1, but not more than 3, hydroxyl group(s), preferably 1 hydroxyl group, and either R 2 and R 3 independently of one another represent C**-CiQ-alkyl which is optionally substituted by 1 to 3 radicals selected from the group comprising hydroxyl, amino and halogen (such as fluorine, chlorine, bromine or iodine), C5-C7-cycloalkyl, preferably cyclohexyl, C ⁇ -C ⁇ -aryl, preferably phenyl, with the proviso that the total of the C atoms of R 2 and R 3 is not less than 3, or R 2 and R 3 together represent an alkylene radical which, together with the carbon atom which carries the radicals R 2 and R 3 , forms a 5-7- membered ring, it being possible for this alkylene radical, in turn, to be substituted by Ci-C ⁇ -alkyl groups.
  • Preferred radicals R 2 and R 3 comprise methyl, isopropyl and tert.- butyl.
  • the length of the radicals R 2 and R 3 influences the effect of the compounds I: shorter radicals lead to an immediate, short effect; longer radicals lead to a delayed, but prolonged effect.
  • An important aspect for the cosmetics industry is the solubility of the compounds in water; this is the case, in particular, with short radicals R 2 and R 3 .
  • Preferred radicals R 1 embrace 1 ,2- and 1 ,3-alkylene radicals which, together with the two oxygen atoms and with the carbon atom to which the two oxygen atoms are attached, form a dioxolane or dioxane ring.
  • Preferred compounds I in which R2 and R3 together represent an alkylene radical are those of the formula
  • R* to R15 independently of one another denote hydrogen or C*
  • Preferred compounds of the formula la are those in which the total of m + n is 1 , i.e. ketals of an optionally substituted cyclohexanone.
  • Preferred substituents are methyl, isopropyl and tert.-butyl.
  • ketals I can be prepared by known processes.
  • ketal I will generally be prepared by acid-catalysed reaction of the ketone on which ketal I is based and not less than the equivalent amount of aliphatic Cs-C ⁇ -alco ol having not less than 3 and not more than 5, preferably 3, hydroxyl groups.
  • the ketone on which ketal I is based and not less than 0.5 mol equivalents but, as a rule, a 1.2- to 4-fold, preferably 1.5- to 3-fold excess of this amount of the Cs-C ⁇ -alcohol having 3 to 5 hydroxyl groups will be employed.
  • acid catalysts which can be used are p-toluenesulphonic acid, phosphoric acid or potassium hydrogen sulphate in catalytically effective amounts (for example 0.1 to 3 g of p-toluenesulphonic acid per mole of ketone).
  • the reaction will preferably be carried out either in an organic solvent which together with water forms an azeotrope, so that the water, which is liberated during the formation of the ketal, can be eliminated by azeotropic entrainment, or water-consuming coreagents such as, for example, trialkyl ortho esters are used.
  • preferred organic solvents comprise benzene, toluene, xylene, chloroform, methylene chloride and trichloroethylene.
  • reaction can be regarded as complete when water no longer separates out or when an ester/alcohol mixture is no longer separated out. It is recommended to wash the products subsequently with dilute alkali and with water, to separate and dry the organic phase, to strip off the solvent and, if appropriate, to purify the residue, for example by distillation.
  • Particularly preferred ketals I are those of the formulae
  • the invention also relates to the ketals III to VI.
  • the ketals I to be employed in the compositions according to the invention can have asymmetric C atoms; optical isomerism can therefore occur. Depending on the starting material and the preparation methods used, they can exist in the form of mixtures of the optical isomers or in the form of pure isomers. The cooling effect of the isomers may differ, so that one or the other isomer may be preferred.
  • Menthol is another coolant which may be used in the present invention.
  • Menthol is a component of peppermint oil and is widely used in oral care products, food stuffs, and cosmetics.
  • diol is a diol.
  • Preferred diols are those set forth in U.S. Patent 4,459,425 to Amano et al, July 10, 1984, incorporated herein in total by reference.
  • a preferred diol is 3-1-methoxy propane-1 ,2-diol.
  • the coolant compounds can be used in any effective amount in the present compositions. Generally the level in the compositions is from about 0.01% to about 1%, preferably from about 0.05 % to about 0.60%, more preferably from about 0.07% to about 0.29%.
  • Carrier :
  • compositions in which the aforedescribed coolant materials find application are many and varied. These compositions include a wide variety of compositions for consumption by or application to the human body. Broadly speaking, these compositions can be divided into comestible and topical compositions, both terms being taken in their broadest possible sense. Thus comestible is to be taken as including not only foodstuffs and beverages taken into the mouth and swallowed, but also other orally ingested compositions taken for reasons other than their nutritional value, e.g., ingestion tablets, antacid preparations, laxatives etc. Comestible compositions also include edible compositions taken by mouth, but not necessarily swallowed, e.g. chewing gum.
  • Topical compositions include not only compositions such as perfumes, powders and other toiletries, lotions, liniments, oils and ointments applied to the external surfaces of the human body, whether for medical or other reasons, but also compositions applied to, or which, in normal usage, come in contact with internal mucous membranes of the body, such as those of the nose, mouth, or throat, whether by direct or indirect application or inhalation, and thus include nasal and throat sprays, dentifrice, mouthwash and gargle compositions. Also included within the present invention are toilet articles such as cleansing tissues and toothpicks impregnated or coated with the active cooling compound.
  • compositions included within the scope of this invention are tobacco and associated articles e.g. pipe and cigarette filters, especially filter tips for cigarettes.
  • the cooling compositions will usually be incorporated into a carrier which may be completely inert or which may be or contain other active ingredients.
  • a carrier which may be completely inert or which may be or contain other active ingredients.
  • carriers include solids, liquids, emulsions, foams and gels.
  • Typical carriers for the cooling compositions include aqueous or alcoholic solutions; oils and fats such as hydrocarbon oils, fatty acid esters, long chain alcohols and silicone oils; finely divided solids such as starch or talc; cellulosic materials such as paper tissue; tobacco; low-boiling hydrocarbons and halohydrocarbons used as aerosol propellents; gums and natural or synthetic resins.
  • Edible or potable compositions including alcoholic and non ⁇ alcoholic beverages, confectionery, frostings, chewing gum; cachous; ice cream; jellies.
  • Toiletries including after shave lotions, shaving soaps, creams and foams, toilet water, deodorants and antiperspirants, "solid colognes", toilet soaps, bath oils and salts, shampoos, hair oils, talcum powders, face creams, hand creams, sunburn lotions, cleansing tissues, dentifrices, toothpicks, dental floss, toothbrushes, mouthwashes, hair tonics, denture adhesives.
  • Medicaments including antiseptic ointments, liniments, lotions, decongestants, counter-irritants, cough mixtures, throat lozenges, antacid and indigestion preparations, oral analgesics.
  • Tobacco preparations including cigars, cigarettes, pipe tobacco, chewing tobacco and snuff; tobacco filters, especially filter tips for cigarettes.
  • Miscellaneous compositions such as water soluble adhesive compositions for envelopes, postage stamps, adhesive labels etc.
  • the edible and potable compositions of this invention will contain the cooling composition in combination with an edible carrier and usually a flavoring or coloring agent.
  • the particular effect of the cooling compounds is to create a cool or fresh sensation in the mouth, and in some cases even in the stomach, and therefore the compositions find particular utility in sugar-based confectionery such as chocolate, boiled sweets and candy, in ice cream and jellies and in chewing gum.
  • the formulation of such confections will be by ordinary techniques and according to conventional recipes and as such forms no part of this invention.
  • the coolant composition will be added to the final composition at a convenient point and in amount sufficient to produce the desired cooling effect in the final product. As already indicated, the amount will vary depending upon the particular composition, the degree of cooling effect desired and the strength of other flavorants in the composition.
  • compositions will find most utility in carbonated or noncarbonated soft drinks e.g., fruit, lemonade, cola, etc., but may also be used in alcoholic beverages. Toiletries:
  • cooling compositions Because of the cooling sensation imparted to the skin, a major utility of the cooling compositions will be in a wide range of toilet preparations and toilet articles. The particular preparations discussed below are to be taken as exemplary.
  • a major utility will be in after shave lotions, toilet water etc., where the compounds will be used in alcoholic or aqueous alcoholic solution, such solutions usually also containing a perfume or mild antiseptic or both.
  • compositions will be used in combination with an oil or fat or a natural or synthetic surfactant e.g., a fatty acid salt or a lauroylsulphate salt, the composition usually also containing an essential oil or perfume.
  • a natural or synthetic surfactant e.g., a fatty acid salt or a lauroylsulphate salt
  • the range of soap compositions will include soaps of all kinds, e.g., toilet soaps, shaving soaps, shaving foams etc.
  • a further class of toilet compositions into which the compositions may be incorporated includes cosmetic creams and emollients, such creams and emollients usually comprising a base emulsion and optionally a range of ingredients such as wax, preservative, perfume, antiseptics, astringents, pigments etc. Also included within this class are lipstick compositions, such compositions usually comprising an oil and wax base into which the coolant compositions can be incorporated along with the conventional ingredients, i.e., pigments, perfumes etc. Once again the formulation of such compositions is conventional.
  • compositions for oral hygiene containing the cooling compositions include mouthwash and dentifrice compositions and are preferred compositions.
  • the first will usually comprise an aqueous, alcoholic, or aqueous-alcoholic solution of an antiseptic often colored or flavored for palatability in an amount of from 0.1% to 1.0% by weight.
  • Dentifrice compositions may be of the powder, paste or liquid type and will usually comprise a finely divided abrasive or polishing material, e.g., precipitated chalk, silica, magnesium silicate, aluminum hydroxide or other similar materials well known in the art, and a detergent or foaming agent.
  • a finely divided abrasive or polishing material e.g., precipitated chalk, silica, magnesium silicate, aluminum hydroxide or other similar materials well known in the art
  • a detergent or foaming agent e.g., a detergent or foaming agent.
  • Optional ingredients which may also be included are flavoring agents and colorants, antiseptics, lubricants, thickeners, emulsifiers or plasticizers.
  • pyrophosphate salts such as those described in U.S. 4,515,772, May 7, 1985 to Parran et al, incorporated herein by reference.
  • nonionic antimicrobials such as triclosan described in U.S. 4,894,220, January 16, 1990 to Nabi, et al. Both patents are incorporated herein by reference. Examples of such agent include triclosan and other phenolic compounds.
  • alkali metal bicarbonate such as sodium bicarbonate.
  • alkali metal bicarbonate such as sodium bicarbonate.
  • the preferred coolant blends useful in oral compositions include mixtures of one or more carboxamides with the glycol.
  • the preferred levels of coolants are from about 0.0500 to about 0.2000 for the coolants of the '688 patent and from about 0.0500 to about 0.1000 of the '163 patent coolants.
  • the cooling compositions may be used in a variety of oral medicines, nasal and throat sprays, and topical compositions, particularly where a counter- irritant is required.
  • the coolant compositions may be formulated into antacid and indigestion remedies, in particular those based on sodium bicarbonate, magnesium oxide, calcium or magnesium carbonate, aluminum or magnesium hydroxide or magnesium trisilicate.
  • the coolant compositions may also be included in oral analgesic compositions e.g. with acetylsalicylic acid or its salts, acetamenophin, ibuprofen, naproxen, as well as other propronic derivatives, and in nasal decongestants, e.g., those containing ephedrine.
  • oral analgesic compositions e.g. with acetylsalicylic acid or its salts, acetamenophin, ibuprofen, naproxen, as well as other propronic derivatives
  • nasal decongestants e.g., those containing ephedrine.
  • compositions of this invention are illustrated by the following non-limiting examples. These examples are strictly given for illustration purposes and are not limiting of the invention described herein as many variations are possible without departing from the spirit and scope of the invention as set forth herein..
  • Titanium Dioxide 0.525 0.500 0.350

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Thermotherapy And Cooling Therapy Devices (AREA)
  • Confectionery (AREA)

Abstract

L'invention porte sur des compositions comprenant un vecteur et une combinaison réfrigérante appropriée de glycol et d'un réfrigérant dont le pH est supérieur à environ 8,2 tant dans la composition elle-même que lors de son utilisation.
PCT/US1996/002257 1995-03-16 1996-02-20 Composition refrigerante WO1996028133A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP96905554A EP0814751A1 (fr) 1995-03-16 1996-02-20 Composition refrigerante
AU49285/96A AU4928596A (en) 1995-03-16 1996-02-20 Coolant compositions
MX9706958A MX9706958A (es) 1995-03-16 1996-02-20 Composiciones refrigerantes.
JP8527604A JPH11502195A (ja) 1995-03-16 1996-02-20 清涼組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US40531195A 1995-03-16 1995-03-16
US08/405,311 1995-03-16

Publications (1)

Publication Number Publication Date
WO1996028133A1 true WO1996028133A1 (fr) 1996-09-19

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ID=23603154

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/002257 WO1996028133A1 (fr) 1995-03-16 1996-02-20 Composition refrigerante

Country Status (6)

Country Link
EP (1) EP0814751A1 (fr)
JP (1) JPH11502195A (fr)
AU (1) AU4928596A (fr)
CA (1) CA2214108A1 (fr)
MX (1) MX9706958A (fr)
WO (1) WO1996028133A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998031331A1 (fr) * 1997-01-15 1998-07-23 Unilever N.V. Procede pour rendre les dents plus blanches
US5902568A (en) * 1997-01-15 1999-05-11 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Method for whitening teeth
EP1011643A1 (fr) * 1997-09-18 2000-06-28 Wm. Wrigley Jr. Company Chewing-gum contenant des carboxamides acycliques a liberation regulee
US6455080B1 (en) 1997-12-29 2002-09-24 Wm. Wrigley Jr., Company Chewing gum containing controlled release acyclic carboxamide and method of making
EP1312354A1 (fr) * 2001-11-13 2003-05-21 Noville, Inc. Compositions d'hygiène buccale contenant diglycérole
US6627233B1 (en) 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
EP1541044A1 (fr) * 2002-09-19 2005-06-15 Japan Tobacco Inc. Filtre pour cigarette
WO2010059289A1 (fr) * 2008-11-20 2010-05-27 The Procter & Gamble Company Compositions pour soin personnel fournissant une sensation de refroidissement améliorée
EP2478777A1 (fr) 2005-12-23 2012-07-25 Kraft Foods Global Brands LLC Composition fournissant une sensation de refroidissement sensiblement similaire à celle fournie par le menthol
EP2559424A1 (fr) 2005-10-05 2013-02-20 Kraft Foods Global Brands LLC Compositions de refroidissement comprenant trimethyl isopropyl butanamid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0616821B1 (pt) * 2005-08-15 2022-06-07 Givaudan Sa Método para proporcionar um efeito refrescante em um produto e produto possuindo um efeito refrescante

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FR1312467A (fr) * 1961-09-30 1962-12-21 Produit cosmétique et procédé d'application
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4230688A (en) * 1972-04-18 1980-10-28 Wilkinson Sword Limited Acyclic carboxamides having a physiological cooling effect
WO1993025177A1 (fr) * 1992-06-17 1993-12-23 The Procter & Gamble Company Compositions de rafraichissement a effet piquant attenue
WO1994016674A1 (fr) * 1993-01-27 1994-08-04 Warner-Lambert Company Antiseptique pour bains de bouche a teneur en alcool reduite et preparations
WO1995017879A1 (fr) * 1993-12-29 1995-07-06 The Procter & Gamble Company Composition de dentifrice anti-tartre contenant du thymol
WO1995034276A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de bain de bouche

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1312467A (fr) * 1961-09-30 1962-12-21 Produit cosmétique et procédé d'application
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4230688A (en) * 1972-04-18 1980-10-28 Wilkinson Sword Limited Acyclic carboxamides having a physiological cooling effect
WO1993025177A1 (fr) * 1992-06-17 1993-12-23 The Procter & Gamble Company Compositions de rafraichissement a effet piquant attenue
WO1994016674A1 (fr) * 1993-01-27 1994-08-04 Warner-Lambert Company Antiseptique pour bains de bouche a teneur en alcool reduite et preparations
WO1995017879A1 (fr) * 1993-12-29 1995-07-06 The Procter & Gamble Company Composition de dentifrice anti-tartre contenant du thymol
WO1995034276A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de bain de bouche

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5902568A (en) * 1997-01-15 1999-05-11 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Method for whitening teeth
WO1998031331A1 (fr) * 1997-01-15 1998-07-23 Unilever N.V. Procede pour rendre les dents plus blanches
US7078066B2 (en) 1997-09-18 2006-07-18 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents and method of making
EP1011643A1 (fr) * 1997-09-18 2000-06-28 Wm. Wrigley Jr. Company Chewing-gum contenant des carboxamides acycliques a liberation regulee
US6627233B1 (en) 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
EP1014805A4 (fr) * 1997-09-18 2004-10-20 Wrigley W M Jun Co Chewing-gum contenant des agents rafraichissants physiologiques
EP1011643A4 (fr) * 1997-09-18 2004-10-20 Wrigley W M Jun Co Chewing-gum contenant des carboxamides acycliques a liberation regulee
EP1935252A1 (fr) 1997-09-18 2008-06-25 WM. Wrigley Jr., Company Composition de gomme à mâcher
US7364761B2 (en) 1997-09-18 2008-04-29 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents and method of preparing
US6455080B1 (en) 1997-12-29 2002-09-24 Wm. Wrigley Jr., Company Chewing gum containing controlled release acyclic carboxamide and method of making
EP1312354A1 (fr) * 2001-11-13 2003-05-21 Noville, Inc. Compositions d'hygiène buccale contenant diglycérole
EP1541044A4 (fr) * 2002-09-19 2005-11-16 Japan Tobacco Inc Filtre pour cigarette
EP1541044A1 (fr) * 2002-09-19 2005-06-15 Japan Tobacco Inc. Filtre pour cigarette
US7487782B2 (en) 2002-09-19 2009-02-10 Japan Tobacco Inc. Cigarette filter
EP2559424A1 (fr) 2005-10-05 2013-02-20 Kraft Foods Global Brands LLC Compositions de refroidissement comprenant trimethyl isopropyl butanamid
EP2478777A1 (fr) 2005-12-23 2012-07-25 Kraft Foods Global Brands LLC Composition fournissant une sensation de refroidissement sensiblement similaire à celle fournie par le menthol
WO2010059289A1 (fr) * 2008-11-20 2010-05-27 The Procter & Gamble Company Compositions pour soin personnel fournissant une sensation de refroidissement améliorée
AU2009318056B2 (en) * 2008-11-20 2014-07-24 The Procter & Gamble Company Personal care compositions providing enhanced cooling sensation
EP2346475B1 (fr) 2008-11-20 2017-03-15 The Procter & Gamble Company Compositions pour soin personnel fournissant une sensation de refroidissement améliorée

Also Published As

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JPH11502195A (ja) 1999-02-23
CA2214108A1 (fr) 1996-09-19
AU4928596A (en) 1996-10-02
EP0814751A1 (fr) 1998-01-07
MX9706958A (es) 1997-11-29

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