Oral care compositions
Piperidine substituted imidazole compounds in oral care compositions address stability and solubility issues, enhancing flavor and masking unpleasant tastes, providing cooling or warming effects.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- SYMRISE GMBH & CO KG
- Filing Date
- 2024-10-28
- Publication Date
- 2026-05-07
AI Technical Summary
Oral care products face challenges with phase separation in liquids and poor solubility of active ingredients, particularly sweeteners and vitamins, and the need to mask unpleasant odors or tastes, such as those from fluorine compounds.
Incorporation of piperidine substituted imidazole compounds in oral care compositions, combined with physiological cooling or warming agents, aroma or flavoring compounds, and fragrances, at specific weight ratios, to enhance stability, solubilization, and mask unpleasant flavors.
The imidazole compounds improve the stability and solubility of oral care products, while providing cooling or warming effects, enhancing flavors, and masking unpleasant tastes, particularly from fluorine derivatives and bitter compounds.
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Abstract
Description
Oral care compositionsAREA OF INVENTION
[0001] The present invention refers to the area of oral care and concerns new compositions comprising selected imidazole compounds for improved stability, solubility and taste.BACKGROUND OF THE INVENTION
[0002] Oral care products include products of various consistencies, such as liquids (e.g., mouthwashes), pastes (toothpaste), gums (chewing gums) or solids (candies). Depending on their physical nature, their formulation poses different problems: Liquid products tend to phase separation, while many active ingredients, particularly sweeteners and vitamins, are difficult to incorporate homogeneously into pasty or gummy preparations due to poor solubility ..Another widespread problem, both in the field of oral care products, is to mask the unpleasant odor or taste of ingredients that cannot be replaced in the formulation. A typical example is fluorine compounds used in dental care products.
[0003] There is a constant need for substances that perform important tasks in the above- mentioned preparations, such as for example providing a physiological cooling effect on the skin or mucous membrane, while also exhibiting other properties that are important for the formulation. Special interest is shown in preparations which, preferably even in very small quantities, are capable of intensifying positive taste or odor impressions or of bringing them to bear in the first place.RELEVANT PRIOR ART
[0004] EP 3315492 A1 (KISSEI) discloses novel pyrazol derivatives according to the following formulashowing TRPM8 inhibition activity and are useful particularly for treating or preventing diseases or symptoms caused by hyper-excitability or disorder of afferent neurons.
[0005] WO 2021 074281 A1 (GIVAUDAN) discloses substituted azacycles and their use as TMPR8 modulators for achieving a cooling effect on skin. The compounds are also disclosed together with other physiological cooling agents and flavors for enhancing the cooling properties.
[0006] US 8,143,259 (JANSSEN) refers to cold menthol receptor antagonists according to the following formulafor treating various disorders including pain.Reference is also made to the paper "Transient Receptor Potential Melastin 8 Channel modulation: Cool entryway for treating pain and cancer" by PEREZ DE VEGA et al published in J.Med.Chem 59(22), p10006-10029 (2016). Further literature concerning TRPM8- triggered cold sensation can be found for example in the paper issued by McKerny D.D. et al. titled "Identification of cold receptor reveals a general role for TRP channels in thermosensation", Nature, 416, p52-58 (2002).OBJECT OF THE INVENTION
[0007] Therefore, it has been the object of the present invention providing compositions which are commonly used in oral care compositions and which additionally possess appreciable stabilizing and solubilizing properties, mask unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds; and / or enhance and / or boost the performance of a flavor, a sweetener or a soothing agent.BRIEF DESCRIPTION OF THE INVENTION
[0008] A first object of the present invention refers to an oral care composition comprising or consisting of(a) at least one piperidine substituted imidazole compound selected from the group consisting of(al) 2-methyl-1 -(2-5-(p-tolyl)- 1 H-imidazol-2-yl) butan-1 -one;(a2) 2-(methylthio)-1 -(2-(5-(p-toly I)- 1 H-imidazol-2-yl) pi peridi n- 1 -one;(a3) 2-methyl-2-(methylthio)-1 -(2-(5-(p-tolyl)-1 H-imidazol-2-yl) pi peridi n- 1 -yl) propan-1 -one;(a4) 2,2-dimethyl-1 -(2-(5-(p-tolyl)-1 H-imidazol-2-yl) piperidin-1 -yl) but-3-en-1 -one or mixtures thereof,(b) at least one carrier, and(c1) at least one physiological cooling or warming agent and / or(c2) at least one aroma or flavoring compound, and / or(c3) at least one fragrance whereby the compounds are present in a ratio by weight (a):(c1 +c2+c3) of from about 1:1,500,00:1 to about 1 :1, preferably from 1 :500,000 to about 1 :10. More preferably from about 1:100,000 to about 1 :100, and most preferably from about 1 :40,000 to about 1 :500.
[0009] In a first embodiment the compositions according to the present invention include compound (a) and one additional additive, namely compound (c1), compound (c2) or compound (c3). However, it is also possible having compositions with three or four components. For ternary mixtures the preferred ratios by weight (c1 :c2), (c1 :c3) or (c2):(c3) are from about 10:90 to about 90:10 and preferably from about 25:75 to about 75:25. For quaternary mixtures the preferred ratios by weight (c1):(c2):(c3) are from about 30:30:40 to about 40:30:30. Each of these sub-groups represent individually preferred embodiments of Compound (a).
[0010] Surprisingly, it was found that the specific imidazole compounds forming component (a) together with physiological cooling or warming substances, flavors and / or fragrances, are suitable for increasing stability of oral care compositions. If these mixtures are used, on one hand they fulfill their actual task, namely, for example, to produce a cooling / warming effect on the skin or to impart a certain flavor or fragrance to a particular product, but also preserves the products against separation, particularly at higher and lower storage temperatures and longer storage times. At the same time, adding the imidazole compounds to oral compositions supports solubilization of actives such as for example sweeteners, vitamins and the like. Moreover, the imidazole compounds possess the ability to mask unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds.Piperidine substituted imidazole compounds
[0011] Substituted imidazole compounds forming group (a) belong to the group of TRMP8 modulators. The structures and their synthesis are known from WO 2021 074281 A1 which is hereby incorporated by reference.Carriers
[0012] The at least one carrier can be a solvent, such as water, ethanol or any polyhydric alcohol suitable for oral uptake. In the alternative the carrier can be the base or the matrix for a candy, a tablet or a chewing gum as discussed infra.Physiological cooling agents
[0013] Physiological cooling agents forming group (d - 1) are chemical substances initiating a cooling effect when brought into contact with human skin or mucosa. Typically, these agents represent menthol or menthol compounds are preferably selected from the group formed by the species depicted in the following table (including their optical isomers and racemates):Menthol derivatives
[0014] A first important representative of the substances forming component (b) is mono- menthyl succinate, which as a substance was patented as early as 1963 by Brown & WilliamsonTobacco Corp. (US 3,111,127) and as a refrigerant is the subject of property rights US 5,725,865and 5,843,466 (V.Mane Fils). Both the succinate and the analogous monomenthyl glutarate are important representatives of monomenthyl esters based on di- and polycarboxylic acids:
[0015] Examples of applications of these substances can be found, for example, in the printed documents WO 2003 043431 (Unilever) or EP 1332772 A1 (IFF).
[0016] The next important group of menthol compounds preferred in the sense of the invention comprises carbonate esters of menthol and polyols, such as glycols, glycerol or carbohydrates, such as menthol ethylene glycol carbonates, menthol propylene glycol carbonates, menthol 2-methyl-1,2-propanediol carbonates or the corresponding sugar derivatives:Menthol ethylene glycol carbonate
[0017] The use of such substances as a cooling agent for cigarettes is, for example, the subject of the 1968 publication US 3,419,543 (Mold et al.); their use as a physiological cooling agent is claimed in DE 4226043 A1 (H&R).
[0018] In the sense of the invention, the menthol compounds menthyl lactate) and, in particular, menthone glyceryl acetal or menthone glyceryl ketal are preferred.
[0019] The former structure is obtained by esterification of lactic acid with menthol, the latter by acetylation of menthone with glycerol (cf. DE 2608226 A1, H&R). This group of compounds also includes 3-(l-menthoxy)-1, 2, propanediol, also known as Cooling Agent 10 (US 6,328,982, TIC), and 3-(l-menthoxy)-2-methyl-1, 2, propanediol, which has an additional methyl group.1.2-orooanediol
[0020] For example, 3-(l-menthoxy)-1, 2, propanediol is prepared starting from menthol according to the following scheme (see US 4,459,425, Takasago):
[0021] Alternative routes in which menthol is reacted with epichlorohydrin in the first step are described in US 6,407,293 and US 6,515,188 (Takasago). The following is an overview of preferred menthol compounds characterized by CO bonding:
[0022] Among these substances, menthone glyceryl acetal / ketal and menthyl lactate as well as menthol ethylene glycol carbonate and menthol propylene glycol carbonate.WS cooling agents
[0023] In the 1970s, menthol compounds were developed for the first time which have a C-C bond in the 3-position and of which a number of representatives can also be used in the sense of the invention. These substances are generally referred to as WS types. The basic body is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1). All other WS types are derived from this structure, such as the species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30, which are also preferred in the sense of the invention. The following two diagrams show the synthesis routes:
[0024] The esters derived from WS-1 are described, for example, in US 4,157,384, and the corresponding N-substituted amides in J. Soc. Cosmet. Chem. pp. 185-200 (1978).
[0025] Physiological cooling agents which are particularly preferred encompass the following species:• Menthol• Menthol glyceryl acetal• Menthol glyceryl ketal• Menthol menthyl ether• Menthone glyceryl acetal• Menthone glyceryl ketal• Menthoxy-1,2-propandiol• Menthoxy-2-methyl-1,2-propanediol• Menthyl acetate• Menthyl ethylene glycol carbonate• Menthyl formiate• Menthyl glutamate• Menthyl glycerol carbonate• Menthyl hydroxy isobutyrate• Menthyl isobutyrate• Menthyl lactate• Menthyl malonate• Menthyl methyl ether• Menthyl N-ethyl oxamate• Menthyl propylene glycol carbonate• Menthyl pyroglutamate• Menthyl-(2-methoxy)acetate• Menthyl-(2-methoxyethoxy)acetate• Menthyl succinate• O-Menthyl succinic acid ester amide• O-Menthyl succinic acid ester-NN-(dimethyl)amide• Menthane carboxylic acid-N-(4-cyanophenyl)amide• Menthane carboxylic acid-N-(4-cyanomethylphenyl)amide• Menthane carboxylic acid-N-ethylamide (WS-3)• (WS-4)• N“-(menthane carbonyl) glycine ethylester (WS-5)• (1 R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1 -isopropyl)cyclohexane- carboxamide (WS-12)• (WS-14)• 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide (WS23)• Isopulegol acetate• p-Menthane-3,8-diol• Cubebol• 3-Methyl-2(1 -pyrrolidinyl)-2-cyclopentene-1 -one)• Tetrahydropyrimidine-2-oneN-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide[(1 R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] 2-(ethylamino)-2-oxo-acetatePhysiological warming agents
[0026] Physiological warming agents forming group (c1-2) are chemical substances initiating a warming effect when brought into contact with human skin or mucosa. Suitable warming agents encompass the following species:• vanillyl derivatives, preferably vanillyl ethers• capsaicin;• allyl isothiocyanate;• gingerol;• 4-(l-menthoxymethyl)-2-phenyl-l;3-dioxolan;• 4-(l -menthoxymethyl)-2-(3';4'-dihydroxyphenyl)-l;3-dioxolan;• 4-(l-menthoxymethyl)-2- (2'-hydroxy-3 '-methoxyphenyl)-3-dioxolan;• 4-(l-menthoxymethyl)-2-(4'-methoxyphenyl)-3-dioxolan;• 4-(l-menthoxymethyl)-2-(3';4'methylenedioxyphenyl)-3 -dioxolan;• 4-(l-menthoxymethyl)-2-(3 '-methoxy-4'-hydroxyphenyl) -3 -dioxolan;• red pepper oil;• red pepper oleoresin;• ginger oleoresin;• nonylic acid vanillyl amide;• jambu oleoresin;• Zanthoxylum pieritum extract;• sanshool I;• sanshool II;• sanshoamide;• black pepper extract;• chavicine;• piperine;• spilanthol;• the modulators or warming agents disclosed in US 6,780,443 (as far as the nature of the modulators are concerned this document is hereby incorporated by reference) and mixtures thereof.
[0027] In a preferred embodiment said warming agent represent a vanillyl ether according to formula (I)wherein R1stands for hydrogen, or a C1-C7 alkyl group; R2stands for a C1-C3 alkyl radical, R3stands for hydrogen or a C3-C9 alkoxyl group; R4stands for hydroxyl or a -OC(O)CH3 group; and wherein R2and R3can be covalent bounded to form a cyclic acetal; said acetal optionally substituted by a C2-C8 alkyl group.
[0028] In a particularly preferred embodiment said warming agents represent a vanillyl ether according to formula (II)(ID wherein R1stand for hydrogen or a C1-C7 alkyl group.
[0029] Most preferred said warming agents represent a vanillyl ether according to formula (III)(Ill = Vanillyl butyl ether VEB)Aroma or flavoring compounds
[0030] Aroma compounds and flavouring agents forming group (c2) are well known in the art and can be chosen from synthetic flavouring liquid and / or oils derived from plants leaves, flowers, fruits and so forth, and combinations thereof. Representative flavouring liquids include: artificial, natural or synthetic fruit flavours such as eucalyptus, lemon, orange, banana, grape, lime, apricot and grapefruit oils and fruit essences including apple, strawberry, cherry, orange, pineapple and so forth; bean and nut derived flavours such as coffee, cocoa, cola, peanut, almond and so forth; and root derived flavours such as licorice or ginger.
[0031] Suitable aroma or flavouring compounds encompass the following species:• 12-methyltridecanal;• acetaldehyde;• acetanisole;• acethylthiazole-2;• acethylthiazoline-2;• acetic acid;• acetyl methylcarbinol;• acetyl pyrazine-2;• acetyl pyridine-2;• allyl capronate;allyl isothiocyanate; amyl cinnamaldehyde-alpha;• anethole;• anisaldehyde-para;• anisic alcohol;• benzaldehyde;• benzyl acetate;• borneol-l;• butyl acetate;• butylidene phthalide-3;• butyric acid;• camphor;• caproic acid;• carvacrol;• carvomenthone;• carvon-d;• carvon-l;• carvylacetate-cis;• caryophyllene;• cineole-1;4;• cineole-1;8;• cinnamalcohol;• cinnamaldehyde;• cinnamyl acetate;• citral;• citronellal;• citronellol;• citronellyl acetate;• cresol• cuminaldehyde;• cyclopentadecanolide;• damascenone-alpha;• damascenone-beta;• damascone-alpha;• damascoe-beta;• decadienal-2;4;• decadienal-2;4;• decalactone delta;• decalacton gamma;• decanal;• dehydromenthofurolactone;• diallyl disulfide;• diethylpyrazine-2;3;• dihydroanethol;• di hydrocarvone;• di hydrocoumarin;• dihydroionone-beta;• dihydromenthofurolactone;• dihydronootkatone;• dimethyl lanthranilate;• dimethyl isopropyldithiazine;• dimethyl pyrazine;• dimethyl sulfide;• diphenyloxide;• divanilline;• d-menthol;• d-menthone;• d-menthyl acetate;• dodecalactone-delta;• dodecalactone-gamma;• epithiomenthan-1;8;• ethyl acetate;• ethyl butyrate;• ethyl capronate;• ethyl caprylate;• ethyl cinnamate;• ethyl isobutyrate;• ethyl isovaleria-nate;• ethyl lactate;• ethyl maltol;• ethyl methyl butyrate-2;• ethyl methyl thiopropionate;• ethyl phenol-4;• ethyl vanillin;• eugenol;• fenchol;• filbertone;• frambinone methyl ether;• frambinone;• furaneol;• furfurylthiol;• geraniol;• geranyl acetate;• geranyl isobutyrate;• guaiacol;• heliotropin;• heptalactone-gamma;• heptanone-2;• heptenal-Z-4;• hexalactone-gamma;• hexanal• hexanol;• hexenol-E-2;• hexenol-Z-3;• hexenyl acetate-E-2;• hexenyl acetate-Z-3;• hexenyl capronate-Z-3;• hexyl acetate;• hexyl cinnamaldehyde-alpha;• hotrienol;• indole;• ionon-beta;• ionone-alpha;• isoamyl acetate;• isoamyl butyrate;• isoamyl isovaerianate;• isobutyl acetate;• isobutyl thiazole;• isobutylmethoxypyrazine• isobutyraldehyde;• isoeugenol;• Isomenthon;• isopropylmethoxypyrazine;• isopropylmethylpyrazine-2;4;• isopulegol;• isova-leraldehyde;• jasmine lactone;• jasmon cis;• ketoisophorone;• limonene-d;• linalool oxide;• linalool-d;• linalool-l;• linalyl acetate;• l-menthol;• l-menthone;• l-menthyl acetate;• maltol;• massoilactone;• melonal;• menthadienyl acetate;• menthofurolactone;• menththiol-1;8;• methional;• methoxymethylpyrazine-2;3;• methyl anthranilate;• methyl butyl acetate-2;• methyl butyrate;• methyl cinnamate;• methyl dihydrojasmonate;• methyl furanthiol-2;3;• methyl jasmonate;• methyl salicylate;• methyl tetrahydrofuranthiol-2;3;• methyl thiobutyrate;• methyl thiohexyl acetate- 1;3;• methylcyclopen-tenolone;• methylthiohexanol-1;3;• myrtenal;• naringin;• neo-menthol;• neral;• nerol;• nerylacetate;• nonadienal-2;4;• nonadienal-2;6;• nonalactone delta;• nonalactone gamma;• nonenal-E-2;• nonenal-Z-6;• nonenol-Z-6;• nootkatone;• octalactone gamma;• octalactone delta;• octanal• octenol- 1;3;• pellitorin;• pentenone-1;3;• pentyl acetate;• phenyl ethyl acetate;• phenyl ethyl alcohol;• phenyl acetaldehyde;• pinene-alpha;• pinene-beta;• piperitanate;• piperitone• prenyl thioacetate;• prenyl thiol;• reubenamine;• rose oxide;• rubescenamine;• sabinene hydrate;• scatole;• sotolone;• styrolyl acetate;• terpinenol-4;• terpineol;• thiohexanol-1;3;• thiohexyl acetate- 1;3;• thiomenthanone-8;3;• thiopenta none-4;4;2;• thymol;• tridecatrienal;• trimethyl pyrazine;• undecadienal-2;4;• undecalactone-gamma and delta;• undecatriene;• vanillin;• vinyl guaiacol;• whisky lactone; and mixtures thereof.
[0032] In particular preferred aroma or flavouring compounds encompass menthol, cineol, eugenol, thymol, cinnamic aldehyde, peppermint oil, spearmint oil, eucalyptus oil, thyme oil, cinnamon oil, clove oil, spruce needle oil, fennel oil, sage oil, aniseed oil, star anise oil, chamomile oil, and caraway oil, and their mixtures.Fragrances
[0033] The fragrances forming group (c3) can be used as single components or in the form of more or less complex mixtures. The species may be obtained from natural sources or prepared by organic synthesis.Natural perfumes
[0034] Natural perfumes include the extracts of blossoms (lily, lavender, rosejasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, for example civet and beaver, may also be used.
[0035] Typically, the synthetic fragrances represent aldehydes, ketones, alcohols, ethers, esters, hydrocarbons their mixtures. In the following these types of fragrances are illustrated but not limited by examples:Aldehydes
[0036] Examples for suitable fragrances showing an aldehyde structure encompass melonal, triplal, ligustral, adoxal, anisaldehyde, cymal, ethylvanillin, florhydral, floralozon, helional, heliotropin, hydroxycitronellal, koavon, laurinaldehyde, canthoxal, lyral, lilial, adoxal, anisaldehyde, cumal, methyl-nonyl-acetaldehyde, citronellal, citronellyloxy-acetaldehyde, cyclamenaldehyde, bourgeonal, p-tert.-bucinal, phenylacetaldehyde, undecylenaldehyde, vanillin; 2,6,10-trimethyl-9-undecenal, 3-dodecen-l-al, oc-n-Amylzimtaldehyde, 4-methoxy- benz-aldehyde, benzaldehyde, 3-(4-tert-butylphenyl)-propanal,2-methyl-3-(para-methoxy- phe-nylpropanal), 2-methyl-4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal,3-phenyl-2-pro- penal, cis- / trans-3,7-dimethyl-2,6-octadien-l-al, 3,7-dimethyl-6-octen-l-al,[(3,7-dimethyl-6- octenyl)-xy]-cetaldehyde, 4-isopropylbenzyaldehyde, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2, 4-dimethyl-3-cyclohexen-1 -carboxyaldehyde, 2-methyl-3-(isopropyl- phenyl)propanal, decyl aldehyde, 2,6-dimethyl-5-heptenal; 4-(tricyclo[5.2.1.0 (2,6)]-decylidene- 8)-butanal; octahydro-4,7-methano-IH-indenecarboxaldehyde; 3-ethoxy-4- hydroxybenzaldehyde, para-ethyl-alpha,alpha-dimethylhydrozimtaldehyde, oc-methyl-3,4- (methylenedioxy)-hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, oc-n-hexyl- cinnamaldehyde, m-cymene-7-carboxaldehyde, oc-methylphenylacetaldehyde, 7-hydroxy-3,7- dimethyl octanal, undecenal, 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,4-(3)(4-methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde, 1 -dodecanal, 2,4-dimethyl-cyclohexene-3- carboxaldehyde,4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-dehyde, 7-methoxy- 3,7-dimethyloctan-1-al, 2-methyl undecanal, 2-methyl decanal, 1 -nonanal, 1 -octanal, 2,6,10- trimethyl-5,9-undecadienal, 2-methyl-3-(4-tertbutyl)propanal, 3-(4-ethylphenyl)-2,2- dimethylpropanal, 3-(4-methoxyphenyl)-2-methylpropanal, methylno-nylacetaldehyde, 2- phenylpropan-1 -al, 3-phenylprop-2-en-1 -al, 3-phenyl-2-pentylprop-2-en-1 -al, 3-phenyl-2- hexylprop-2-enal, 3-(4-isopropylphenyl)-2-methylpropan-1-al, 3-(4-ethylphenyl)-2,2- dimethylpropan-1 -al, 3-(4-tert-butylphenyl)-2-methyl-propanal, 3-(3,4-Methylendioxy- phenyl)-2-methylpropan-1 -al,3-(4-Ethylphenyl)-2,2-dimethylpropanal, 3-(3-lsopropylphenyl)- butan-1 -al, 2,6-Dimethylhept-5-en-1 -al,Dihydrozimtaldehyde, 1 -methyl-4-(4-methyl-3- pentenyl)-3-cyclohexene-1 -carboxaldehyde, 5- or 6-Methoxyhexahydro-4,7-methanoindan-1 or 2-carboxyaldehyde, 3,7-dimethyloctan-1 -al, 1-undecanal, 10-undecen-1 -al, 4-hydroxy-3- methoxybenzaldehyde, 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyaldehyde, 7- hydroxy-3,7-dimethyl-octanal; trans-4-decenal, 2,6-nonadienal, p-tolylacetaldehyde; 4- methylphenylacetaldehyde, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1 -yl)-2-butenal, o- methoxyzimtaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3,7-dimethyl-2- methylene-6-octenal, phenoxyacetaldehyde; 5,9-dimethyl-4,8-decadienal, peony aldehyde (6,10-dimethyl-3-oxa-5,9-undecadien-1 -al), hexahydro-4,7-methanoindan-1 -carboxaldehyde, octanal, 2-methyl octanal, alpha-methyl-4-(l-methylethyl)benzene-acetaldehyde, 6,6- dimethyl-2-norpinene-2-propionaldehyde, p-methyl phenoxy acetaldehyde, 2-methyl-3- phenyl-2-propen-1 -al, 3,5,5-trimethylhexanal, hexahydro-8, 8-dimethyl-2-naphthaldehyde, 3- propyl-bicyclo[2.2.1]-hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1 -pentanal,methylnonyl acetaldehyde, 1 -p-menthene-q-carboxaldehyde, citral or its mixtures, lilial citral, 1 -decanal, n-undecanal, n-dodecanal, hlorhydral, 2,4-dimethyl-3-cyclohexen-1 - carboxaldehyde 4-methoxybenzaldehyde, 3-methoxy-4-hydroxy-benzalde-hyde, 3-ethoxy-4- hydroxybenzaldehyde, 3,4-methylendioxybenzaldehyde, 3,4-dimethoxybenzaldehyde and their mixtures.Ketones
[0037] Examples for suitable fragrances showing a ketone structure encompass buccoxime, iso jasmone, methyl beta naphthyl ketone, moschus indanone, tonalid / moschus plus, oc- damascone, |3-damascon, S-damascone, Iso-damascone, damascenone, damarose, methyl- dihydrojasmonate, menthone, carvone, campher, fenchone, alphalonen, |3-iononw, dihydro-p- lonone, y-methylionone, fleuramone, dihydrojasmone, cis-Jasmon, iso-E-Super, methyl cedrenylk etone, or methyl cedrylon, acetophenone, methyl aceto phenone, p- methoxyacetophenone, methyl-|3-naphtyl ketone, benzylacetone, benzophenone, p-hydroxy phenylbutanone, celery Ketone or livescon, 6-osopropyl-deca-hydro-2-naphtone, dimethyloctenone, freskomenth, 4-(l-ethoxyvinyl)-3,3,5,5,-tetramethylv cyclohexanone, methylheptenone, 2-(2-(4-Methyl-3-cyclohexen-1 -yl)propyl)-cyclopentanone, 1 -(p-men- thene-6(2)-yl)-1 -propanone, 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 2-Acetyl-3,3-di- methyl-norbornan, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 4-damascol, dulcinyl or cassione, gelsone, hexalone, isocyclemone E, Methylcyclocitrone, methyl lavender ketone, orivone, p-tert-butyl cyclohexanone, verdone, delphone, muscone, neobutenone, plicatone, veloutone, 2,4,4,7-tetramethyl-oct-6-en-3-one, tetrameran, hedion and their mixtures. The preferred ketones are selected from the group comprising oc-damascone, S-damascone, iso- damascone, carvone, y-methyl ionone, Iso-E-Super, 2,4,4,7-tetramethyl-oct-6-en-3-one, benzylacetone, |3-damascone, damascenone, methyl dihydrojasmonate, methyl cedrylone, hedione and their mixtures
[0038] As explained above, said ketones or said aldehydes may show an aliphatic, cycloaliphatic, aromatic, ethy lenica I ly unsaturated structure or a mixture of these elements. The components may also include heteroatoms or show a polycyclic structure. Suitable substituents for all these structures are hydroxyl and / or amino groups. Further fragrances are compiled in the following document: Steffen Arctander „Published 1960 and 1969 respectively, Reprinted2000 ISBN: Aroma Chemicals Vol. 1 : 0-931710-37-5, Aroma Chemicals Vol. 2: fl- 931710-38-3", which is hereby incorporated by reference.Alcohols
[0039] Suitable fragrance alcohols encompass for example 10-undecen-1 -ol, 2,6- dimethylheptan-2-ol, 2-methylbutanol, 2-methylpentanol,2-phenoxyethanol, 2- phenylpropanol, 2-tert-Butycyclohexanol, 3,5,5-trimethylcyclohexanol, 3-hexanol, 3-methyl-5-phenylpentanol, 3-octanol, 1-octen-3-ol, 3-phenylpropanol,4-heptenol, 4- isopropylcyclohexanol, 4-tert-butycyclohexanol, 6,8-dimethyl-2-nonanol,6-nonen-1-ol, 9- decen-1-ol, oc-methyl benzylalcohol, oc-terpineol, amylsalicylat, benzyl alcohol, benzyl salicylate, p-terpineol, butyl salicylate, citronellol, cyclohexyl salicylate, decanol, dihydromyrcenol, dimethyl benzylcarbinol, dimethyl heptanol, dimethyl octanol, ethyl salicylate, ethyl vanilin, anethol, eugenol, geraniol, heptanol, hexyl salicylat, isoborneol, isoeugenol, isopulegol, linalool, menthol, myrtenol, n-hexanol, nerol, nonanol, octanol, para- menthan-7-ol, phenylethylalkohol, phenol, phenyl salicylat, tetrahydro geraniol, tetrahydro linalool, thymol, trans-2-cis-6-nonadienol, trans-2-nonen-1-ol, trans-2-octenol, undecanol, vanillin, cinnamalcohol and their mixtures.Esters
[0040] Examples for suitable fragrances showing a ketone structure encompass benzyl acetate, phenoxyisobutyrate, p-tert.-butylcyclohexylacetate, linalylacetate, dimethylbenzylcarbinylacetate (DMBCA), phenylethylacetate, benzylacetate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate, benzylsalicylate, cyclohexylsalicylate, floramat, melusat, jasmacyclatat and their mixtures.Ethers
[0041] Examples for suitable fragrances showing a ketone structure encompass benzylethyl ether or ambroxan.Hydrocarbons
[0042] Examples for suitable fragrances representing hydrocarbons encompass terpenes, e.g. limonene and pinen.
[0043] Fragrances which are particularly preferred encompass the following species:• [(3,7-dimethyl-6-octenyl)-xy]-cetaldehyde,• 1 -(p-menthene-6(2)-yl)-1 -propanone,• 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde,• 10-undecen-1-al,• 10-undecen-1-ol,• 1 -decanal,• 1-dodecanal,• 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyaldehyde,• 1 -methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1 - carboxaldehyde,• 1-nonanal,• 1 -octanal,• 1-octen-3-ol,• 1-p-menthene-q-carboxaldehyde,• 1 -undecanal,• 2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)-cyclopentanone,• 2,4,4,7-tetramethyl-oct-6-en-3-one,• 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,• 2, 4-dimethyl-3-cyclohexen-1 -carboxaldehyde 4- methoxybenzaldehyde,• 2, 4-dimethyl-3-cyclohexen-1 -carboxyaldehyde,• 2,6,10-trimethyl-5,9-undecadienal,• 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al,• 2,6-dimethyl-5-heptenal;• 2,6-dimethylhept-5-en-1-al,• 2,6-dimethylheptan-2-ol,• 2,6-nonadienal,• 2-acetyl-3,3-di-methyl-norbornan,• 2-methyl decanal,• 2-methyl octanal,• 2-methyl undecanal,• 2-methyl-3-(4-tertbutyl)propanal,• 2-methyl-3-(isopropyl-phenyl)propanal,• 2-methyl-3-(para-methoxy-phenylpropanal),• 2-methyl-3-phenyl-2-propen-1 -al,• 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal,• 2-methylbutanol,• 2-methylpentanol,• 2-phenoxyethanol,• 2-phenylpropan-1-al,• 2-phenylpropanol,• 2-tert-butycyclohexanol,• 3-(3,4-methylendioxy-phenyl)-2-methylpropan-1 -al,• 3-(3-isopropylphenyl)-butan-1-al,• 3-(4-ethylphenyl)-2,2-dimethylpropan-1 -al,• 3-(4-ethylphenyl)-2,2-dimethylpropanal,• 3-(4-isopropylphenyl)-2-methylpropan-1 -al,• 3-(4-methoxyphenyl)-2-methylpropanal,• 3-(4-tert-butylphenyl)-2-methyl-propanal,• 3-(4-tert-butylphenyl)-propanal,• 3,4-dimethoxybenzaldehyde,• 3,4-methylendioxybenzaldehyde,• 3,5,5-trimethylcyclohexanol,• 3,5,5-trimethylhexanal,• 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde,• 3,7-dimethyl-2-methylene-6-octenal,• 3,7-dimethyl-6-octen-1-al,• 3,7-dimethyloctan-1-al,• 3-ethoxy-4-hydroxybenzaldehyde,• 3-hexanol,• 3-methoxy-4-hydroxy-benzaldehyde,• 3-methyl-5-phenyl-1-pentanal,• 3-methyl-5-phenylpentanol,• 3-octanol,• 3-phenyl-2-hexylprop-2-enal,• 3-phenyl-2-pentylprop-2-en-1-al,• 3-phenyl-2-propenal,• 3-phenylprop-2-en-1-al,• 3-phenylpropanol,• 3-propyl-bicyclo[2.2.1]-hept-5-ene-2-carbaldehyde,• 4-(1-ethoxyvinyl)-3,3,5,5-tetramethyl cyclohexanone,• 4-(3)(4-methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde,• 4-(4-hydroxy-3-methoxyphenyl)-2-butanone,• 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-dehyde,• 4-(t ricyclo [5.2.1 ,0(2,6)]-decylidene-8)-butanal;• 4-damascol,• 4-heptenol,• 4-hydroxy acetophenone• 4-hydroxy-3-methoxybenzaldehyde,• 4-isopropyl benzyaldehyde,• 4-isopropyl cyclohexanol,• 4-methoxy benzaldehyde,• 4-methylphenyl acetaldehyde,• 4-tert-butyl cyclohexanol,• 5,9-dimethyl-4,8-decadienal,• 5-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,• 5-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,• 6,10-dimethyl-3-oxa-5,9-undecadien-1-al,• 6,6-dimethyl-2-norpinene-2-propionaldehyde,• 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone,• 6,8-dimethyl-2-nonanol,6-nonen-1 -ol,• 6-isopropyl-deca-hydro-2-naphtone,• 6-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,• 6-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,• 7-hydroxy-3,7-dimethyl octanal,• 7-methoxy-3,7-dimethyloctan-1-al,• 9-decen-1-ol,• 9-decenal,• acetophenone,• adoxal,• allyl cyclohexylpropionate,• alphalonen,• ambroxan,• amylsalicylat,• anethol,• anisaldehyde,• benzaldehyde,• benzophenone,• benzyl acetate,• benzyl acetone,• benzyl alcohol,• benzyl salicylate,• benzylethyl ether,• bourgeonal,• buccoxime,• butyl lactate,• butyl salicylate,• campher,• canthoxal,• carvone,• cassione,• celery cetone• chlorhydral,• cinnamalcohol,• cis- / trans-3,7-dimethyl-2,6-octadien-1-al,• cis-jasmon,• citral or its mixtures,• citronellal,• citronellol,• citronellyl oxyacetaldehyde,• cumal,• cyclamenaldehyde,• cyclohexyl salicylate,• cymal,• damarose,• damascenone,• decanol,• decyl aldehyde,• delphone,• dihydrojasmone,• dihydromyrcenol,• dihydrozimtaldehyde,• dihydro-fMonone,• dimethyl benzylcarbinol,• dimethyl benzylcarbinylacetate,• dimethyl heptanol,• dimethyl octanol,• dimethyl octenone,• dulcinyl• ethyl salicylate,• ethyl vanilin,• ethylmethylphenyl glycinate,• eugenol,• fenchone,• fleuramone,• flora lozon,• flora mat,• florhydral,• gelsone,• geraniol,• hedione,• helional,• heliotropin,• heptanol,• hexahydro-4, 7-methanoindan-1 -carboxaldehyde,• hexahydro-8, 8-dimethyl-2-naphthaldehyde,• hexalone,• hexyl salicylat,• hydroxycitronellal,• isoborneol,• isodamascone,• isoeugenol,• isojasmone,• isopulegol,• jasmacyclatat,• koavon,• laurinaldehyde,• ligustral,• lilial citral,• lilial,• limonen,• linalool,• linalyl acetate,• livescon,• lyral,• m-cymene-7-carboxaldehyde,• melonal,• melusat,• menthol,• menthone,• methyl acetophenone,• methyl cedrenyl ketone,• methyl cedrylon,• methyl cedrylone,• methyl cyclocitrone,• methyl dihydrojasmonate,• methyl heptenone,• methyl lavender ketone,• methyl-dihydrojasmonate,• methylnonyl acetaldehyde,• methyl-|3-naphthyl ketone,• moschus indanone,• muscone,• myrtenol,• n-dodecanal,• neobutenone,• nerol,• n-hexanol,• nonanol,• n-undecanal,• octahydro-4, 7-methano-1 H-indenecarboxaldehyde;• octanal,• octanol,• o-methoxyzimtaldehyde,• orivone,• p-ethyl-a,a-dimethylhydrozimtaldehyde,• phenol,• phenoxyacetaldehyde;• phenoxyisobutyrate,• phenyl acetaldehyde,• phenyl salicylat,• phenylethyl acetate,• phenylethyl alcohol,• phenylpropyl alcohol• p-hydroxy phenylbutanone,• pinen• plicatone,• p-menthan-7-ol,• p-methoxy acetophenone,• p-methyl phenoxy acetaldehyde,• p-tert.-bucinal,• p-tert.-butyl cyclohexanone,• p-tert.-butyl cyclohexylacetate,• p-tolyl acetaldehyde;• styrallyl propionate,• tetrahydrogeraniol,• tetrahydrolinalool,• tetrameran,• thymol,• tonalid / moschus plus,• trans-2-cis-6-nonadienol,• trans-2-nonen-1-ol,• trans-2-octenol,• trans-4-decenal,• triplal,• undecanal,• undecanol,• undecylenraldehyde,• vanillin,• veloutone,• verdone,• a.-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde,• a-damascone,• oc-methyl benzylalcohol,• oc-methyl-4-(l-methylethyl)benzene-acetaldehyde,• oc-methylphenylacetaldehyde,• oc-amyl cinnamaldehyde,• a-n-hexyl cinnamaldehyde,• oc-terpineol,• |3-damascone,• |3-ionon,• p-terpineol,• y-methylionone,• S-damascone,CompositionsIn a particular preferred embodiment, the compositions according to the present invention comprises the compounds in amounts of(a) 0,0001 to about 0.2 wt. -percent, preferably about 0.001 to about 0.1 wt.-percent, and more preferably from about 0.01 to about 0.05 wt.-percent piperidine substituted imidazole compounds;(b) about 50 to about 99.8 wt.-percent, preferably about 60 to about 90 wt.-percent and more preferably about 70 to about 80 wt.-percent of at least one carrier;(c) about 0.1 to about 1 wt.-percent, preferably about 0.2 to about 0.8 wt.-percent, and more preferably about 0.3 to about 0.5 wt.-percent of at least one physiological cooling or warming agent (component c1, aroma or flavoring compound (component c2) and / or fragrance (component c3), on condition that the amounts add optionally together with further oral care additives 100 wt.-percent.ORAL CARE COMPOSITIONS
[0044] Typical examples for suitable oral compositions encompass (hard boiled) candies, compressed tablets, chewing gums, toothpastes and mouth washes. The manufacture and composition of said oral compositions are described as follows:Candies
[0045] According to the present invention the preferred candies are so-called hard-boiled candies. Their bases are usually prepared from a mixture of sugar and other carbohydrates that are kept in an amorphous or glassy condition. This form can be considered a solid syrup of sugars generally having up to about 4.5 % b.w. moisture, based on the weight of the candy base, with about 0.5 to about 2.5 % b.w. being preferred and about 1.0 to about 1.5 % b.w. being most preferred. Such materials normally contain up to 65 % b.w. corn syrup, up to 80 % b.w. sugar and from 0.1 to 5.0 % b.w. water. Generally, the ratio of sugar (or other sweetener suitable for candy formulation) to corn syrup is within the range of about 70:25 to about 45:55 with about 60:40 being preferred. The syrup component generally is prepared from corn syrups high in fructose, but may include other materials. Further ingredients such as flavourings, sweeteners, acidulents, colorants and so forth may also be added.
[0046] Hard boiled candy bases may also be prepared from non-fermentable sugars such as sorbitol, mannitol, xylitol, maltitol, hydrogenated starch hydrolysate, hydrogenated corn syrup and mixtures thereof. The candy bases may contain up to about 95% sorbitol, a mixture ofsorbitol and mannitol at a ratio of about 9.5 to 0.5 up to about 7.5 to 2.5 and hydrogenated corn syrup up to about 55% of the syrup component.Compressed tablets
[0047] According to the present invention the oral compositions can represent compressed tablets, comprising the liquid flavour in amounts of typically about 0.1 to about 0.6 % b.w. and preferably about 0.5 % b.w.Chewing gums
[0048] Chewing gums typically consist of a water- insoluble vase component, a water-soluble component and additives providing for example a specific flavour.
[0049] The water-insoluble base, which is also known as the "gum base", typically comprises natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, softeners, dyes and optionally waxes. The base normally makes up 5 to 95% by weight, preferably 10 to 50% by weight and more particularly 20 to 35% by weight of the composition as a whole. In one typical embodiment of the invention, the base consists of 20 to 60% by weight synthetic elastomers, 0 to 30% by weight natural elastomers, 5 to 55% by weight plasticizers, 4 to 35% by weight fillers, 5 to 35% by weight softeners and small amounts of additives, such as dyes, antioxidants and the like, with the proviso that they are soluble in water at best in small quantities.
[0050] Suitable synthetic elastomers are, for example, polyisobutylenes with average molecular weights (as measured by GPC) of 10,000 to 100,000 and preferably 50,000 to 80,000, isobutylene / isoprene copolymers ("butyl elastomers"), styrene / butadiene copolymers (styrene:butadiene ratio, for example, 1 :3 to 3:1). polyvinyl acetates with average molecular weights (as measured by GPC) of 2,000 to 90,000 and preferably 10,000 to 65,000, polyisoprenes, poly-ethylenes, vinyl acetate / vinyl laurate copolymers and mixtures thereof. Examples of suitable natural elastomers are rubbers, such as for example smoked or liquid latex or guayuls, and natural gums, such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinba, chicle, gutta hang kang and mixtures thereof. The choice of the synthetic and natural elastomers and their mixing ratios essentially depends on whether or not bubbles are to be produced with the chewing gums (bubble gums). Elastomer mixtures containing jelutong, chicle, sorva and massaranduba are preferably used.
[0051] In most cases, the elastomers are too hard or lack plasticity for satisfactory processing, so that it has been found to be of advantage to use special plasticizers which, of course, must also satisfy in particular all requirements relating to acceptability as food additives. In this respect, suitable plasticizers are, above all, esters of resin acids, for example esters of lower aliphatic alcohols or polyols with completely or partly hydrogenated, monomeric or oligomeric resin acids. In particular, the methyl, glycerol or pentaerythritol esters or mixtures thereof areused for this purpose. Alternatively, terpene resins, which may be derived from .alpha. -pinene, .beta. -pinene, .delta. -limonene or mixtures thereof, could also be used.
[0052] Suitable fillers or texturizers are magnesium or calcium carbonate, ground pumice stone, silicates, especially magnesium or aluminium silicates, clays, aluminium oxides, talcum, titanium dioxide, mono-, di- and tricalcium phosphate and cellulose polymers.
[0053] Suitable softeners or emulsifiers are tallow, hydrogenated tallow, hydrogenated or partly hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids containing 6 to 22 and preferably 12 to 18 carbon atoms and mixtures thereof.
[0054] Suitable dyes and whiteners are, for example, the FD&C types, plant and fruit extracts permitted for colouring foods and titanium dioxide. The gum bases may also contain waxes or may be wax-free
[0055] In addition to the water-insoluble gum base, chewing gum preparations regularly contain a water-soluble component which is formed, for example, by softeners, sweeteners, fillers, flavours, flavour enhancers, emulsifiers, dyes, acidifiers, antioxidants and the like, with the proviso that the constituents have at least adequate solubility in water. Accordingly, individual constituents may belong both to the water-insoluble phase and to the water-soluble phase, depending on the water solubility of the special representatives. However, combinations may also be used, for example a combination of a water-soluble and a water-insoluble emulsifier, in which case the individual representatives are present in different phases. The water-insoluble component usually makes up 5 to 95% by weight and preferably 20 to 80% by weight of the preparation.
[0056] Water-soluble softeners or plasticizers are added to the chewing gum compositions to improve chewability and the chewing feel and are present in the mixtures in quantities of typically 0.5 to 15% by weight. Typical examples are glycerol, lecithin and aqueous solutions of sorbitol, hydrogenated starch hydrolysates or corn sirup.
[0057] Fillers are particularly suitable for the production of low-calorie chewing gums and may be selected, for example, from polydextrose, raftilose, raftilin, fructo-oligosaccharides (NutraFlora), palatinose oligosaccharides, guar gum hydrolyzates (Sun Fiber) and dextrins.
[0058] The chewing gums may additionally contain auxiliaries and additives which are suitable, for example, for dental care, more particularly for controlling plaque and gingivitis, such as for example chlorhexidine, CPC or triclosan. They may also contain pH adjusters (for example buffer or urea), anti-caries agents (for example phosphates or fluorides), biogenic agents (antibodies, enzymes, caffeine, plant extracts), providing these substances are permitted in foods and do not undesirably interact with one another.Toothpastes and mouthwashes
[0059] Toothpastes or tooth creams are generally understood to be paste-like preparations of water, thickeners, humectants, abrasives or polishes, surfactants, sweeteners, flavorings, deodorizing agents and agents active against oral and dental diseases. In toothpastes according to the invention, any of the usual polishes may be used, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminium silicates, calcium pyrophosphate, finely particulate synthetic resins, silicas, aluminium oxide and aluminium oxide trihydrate. Particularly suitable polishes for toothpastes according to the invention are finely particulate xerogel silicas, hydrogel silicas, precipitated silicas, aluminium oxide trihydrate and finely particulate.alpha. -alumina, or mixtures of these polishes. Such polishes are preferably used in quantities of from about 15 to 40% by weight of the toothpaste. Preferred humectants used for toothpastes according to the invention include low molecular weight polyethylene glycols, glycerol, sorbitol or mixtures thereof in quantities of up to about 50% by weight of the toothpaste. Among the known thickeners for use with toothpastes according to the invention, particularly preferred are the thickening, finely particulate gel silicas and nonionic hydrocolloids, such as hydroxy ethyl cellulose, hydroxy propyl guar, hydroxy ethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol and vegetable gums, such as tragacanth, agaragar, carrageen moss, gum arabic and xanthan gum. The desired flavor and aroma for preparations in accordance with the invention may be obtained by adding the components (a) and / or (b) and optionally also (c). It is also advantageous adding caries inhibitors to the oral preparations in the form of, for example, alkali fluorides, alkali monofluorophosphates or alkali salts of organophosphonic acids. In addition, the oral preparations according to the invention may contain other standard auxiliaries, such as dyes, preservatives and opacifiers, for example titanium dioxide. For mouthwashes, the oral compositions according to the invention may readily be combined with aqueous-alcoholic solutions containing different amounts of ethereal oils, emulsifiers, astringent and toning drug extracts, caries-inhibiting additives and flavour correctants.Additives
[0060] The oral compositions of the present invention may include additional additives as for examples sweeteners, vitamins, fluorine compounds, soothing agents and the like in amounts of from about 0.1 to about 10 % wt.-percent, and preferably from about 1 to about 2 wt.- percent each.Sweeteners
[0061] Suitable sweet-tasting substances, including natural sources of these substances (component e5), such as for example sweet-tasting carbohydrates or sugars (e.g. sucrose (synonymous with saccharose), trehalose, lactose, maltose, melizitose, raffinose, palatinose,lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D- tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde, maltodextrin) or vegetable preparations containing predominantly these carbohydrates (e.g. from sugar beet (Beta vulgaris ssp., sugar fractions, sugar syrup, molasses), from sugar cane (Saccharum officinarum ssp., e.g. molasses, sugar syrups), from sugar maple (Acer ssp.), from agave (agave thick juice), synthetic / enzymatic hydrolysates of starch or sucrose (e.g. invert sugar syrup, highly enriched fructose syrups made from corn starch), fruit concentrates (e.g. from apples or pears, apple syrup, pear syrup), sugar alcohols (e.g. erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol), proteins (e.g. miraculin, monellin, thaumatin, curculin, brazzein), sweeteners (magap, sodiumcyclamate, acesulfame K, neohesperidin dihydrochalcone, saccharin sodium salt, aspartame®, superaspartame, neotame, alitame, sucralose, stevioside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, monatin, phyllodulcin), certain sweet-tasting amino acids (glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D- tryptophan, L-proline), other sweet-tasting low-molecular substances (e.g. hernandulcin, dihydrochalcone glycosides, glycyrrhizin, glycyrrhetinic acid ammonium salt or other glycyrrhetinic acid derivatives), liquorice extracts (Glycyrrhizza glabra ssp.), Lippia dulcis extracts, Momordica ssp. extracts or individual substances (in particular Momordica grosvenori [Luo Han Guo] and the mogrosides obtained therefrom), Hydrangea dulcis or Stevia ssp. (e.g. Stevia rebaudiana) extracts or individual substances.Vitamins
[0062] In another embodiment of the present invention the compositions may include vitamins (component el). Vitamins have diverse biochemical functions. Some have hormone- like functions as regulators of mineral metabolism (e.g., vitamin D), or regulators of cell and tissue growth and differentiation (e.g., some forms of vitamin A). Others function as antioxidants (e.g., vitamin E and sometimes vitamin C). The largest numbers of vitamins (e.g. B complex vitamins) act as precursors for enzyme cofactors that help enzymes in their work as catalysts in metabolism. In this role, vitamins may be tightly bound to enzymes as part of prosthetic groups: For example, biotin is part of enzymes involved in making fatty acids. Vitamins may also be less tightly bound to enzyme catalysts as coenzymes, detachable molecules that function to carry chemical groups or electrons between molecules. For example, folic acid carries various forms of carbon group - methyl, formyl, and methylene - in the cell. Although these roles in assisting enzyme-substrate reactions are vitamins' best-known function, the other vitamin functions are equally important. In the course of the present invention suitable vitamins are selected from the group consisting of• Vitamin A (retinol, retinal, beta carotene),• Vitamin Bi (thiamine),• Vitamin B2 (riboflavin),• Vitamin B3 (niacin, niacinamide),• Vitamin Bs (panthothenic acid),• Vitamin Bg (pyridoxine, pyridoxamine, paridoxal),• Vitamin B7 (biotin),• Vitamin B9 (folic acid, folinic acid),• Vitamin B12 (cyanobalamin, hydoxycobalmin, methylcobalmin),• Vitamin C (ascorbic acid),• Vitamin D (cholecalciferol),• Vitamin E (tocopherols, tocotrienols), and• Vitamin K (phyolloquinone, menaquinone).
[0063] The preferred vitamins are ascorbic acid and tocopherols.INDUSTRIAL APPLICATION
[0064] Another object of the present invention refers to a method for• improving stability of an oral care composition;• increasing solubility of active ingredients in an oral care composition; and / or• masking unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds encompassing the step of adding a working amount of the composition according to the present invention to said preparation. Typically, the compositions are added in amounts of from 0.01 to 2 wt. -percent and preferably from about 0.1 to 1 wt.-percent - calculated on the preparations.
[0065] Also claimed is the use of at least one piperidine substituted imidazole compound as indicated above for• improving stability of an oral care composition• increasing solubility of active ingredients in an oral care composition• masking unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds.
[0066] For the sake of good order, it is emphasized that all preferred embodiments, namely mixtures, compositions, ratio and the like also apply to the method and the use as claimed above. Therefore, any repetition is superfluous.EXAMPLESExample 1Masking of bitter taste in a chewing gum
[0067] Chewing gums comprising physiological cooling agents often exhibit an unpleasant bitter and metallic after taste. Two compositions were prepared comprising an imidazole compound according to the invention and another imidazole for comparison. Both compositions were evaluated by a panel consisting of 5 trained individuals vis-a-vis a control. The aftertaste impressions were expressed by numbers from (5) = strong to (1) = almost not recognizable. The results are provided in Table 1; given are the average values. Example 1 is according to the invention, Examples C1 and C2 serve for comparison.Table 1Chewing gum, free of sugar; all amounts in % b.w.
[0068] As one can see, the imidazole compound according to the invention eliminates the bitter and metallic aftertaste, while the comparative imidazole compound has a much weaker effect.Example 2Masking of bitter taste in a tooth paste
[0069] Toothpastes comprising steviosides instead of sugar agents exhibit an unpleasant bitter and metallic after taste. Two compositions were prepared comprising an imidazole compound according to the invention and another imidazole for comparison. Both compositions were evaluated by a panel consisting of 5 trained individuals vis-a-vis a control. The aftertaste impressions were expressed by numbers from (5) = strong to (1) = almost not recognizable. The results are provided in Table 2; given are the average values. Example 2 is according to the invention, Examples C3 and C4 serve for comparison.Table 2Tooth paste; all amounts in % b.w.
[0070] As one can see, the imidazole compound according to the invention eliminates the bitter and metallic aftertaste, while the comparative imidazole compound has a much weaker effect.Example 3Improvement of solubility of allantoin in a mouth wash
[0071] Mouth washes represent aqueous-ethanolic solutions comprising actives, flavours and dyes. Often, solubility of actives in the compositions is poor. For example, allantoin, a prominent active for oral care preparations due its soothing properties, shows a solubility of only 5.7 gl’1at 25 °C. Two compositions were prepared comprising an imidazole compound according to the invention and another imidazole for comparison. Both compositions were evaluated over a storage period of 5 days at 20 and 25 °C. The stability was expressed by numbers from (5) = strong precipitation to (1) = almost no precipitation. The results are provided in Table 3. Example 3 is according to the invention, Examples C5 and C6 serve for comparison.Table 3Mouth wash concentrate; all amounts in % b.w.
[0072] As one can see, the imidazole compound according to the invention keeps the composition stable, while the comparative imidazole compound has a much weaker effect.Example 4Masking of bitter taste in a candy
[0073] Candies comprising artificial sweeteners often exhibit an unpleasant bitter and metallic after taste. Two compositions were prepared comprising an imidazole compound according to the invention and another imidazole for comparison. Both compositions were evaluated by a panel consisting of 5 trained individuals vis-a-vis a control. The aftertaste impressions were expressed by numbers from (5) = strong to (1) = almost not recognizable. The results are provided in Table 4; given are the average values. Example 4 is according to the invention, Examples C7 and C8 serve for comparison.Table 4Hard boiled candy, sugar-free; all amounts in % b.w.
[0074] As one can see, the imidazole compound according to the invention eliminates the bitter and metallic aftertaste, while the comparative imidazole compound has a much weaker effect.
Claims
WHAT CLAIMED IS1. An oral care composition comprising or consisting of(a) at least one piperidine substituted imidazole compound selected from the group consisting of(a1) 2-methyl-1-(2-5-(p-tolyl)-1 H-imidazol-2-yl) butan-1-one;(a2) 2-(methylthio)-1-(2-(5-(p-tolyl)-1 H-imidazol-2-yl) piperidin-1-one;(a3) 2-methyl-2-(methylthio)-1 -(2-(5-(p-toly I)- 1 H-imidazol-2-yl) pi peridi n- 1 -yl) propan-1 -one;(a4) 2,2-dimethyl-1-(2-(5-(p-tolyl)-1 H-imidazol-2-yl) piperidin-1-yl) but-3-en-1- one or mixtures thereof,(b) at least one carrier, and(c1) at least one physiological cooling or warming agent and / or(c2) at least one aroma or flavoring compound, and / or(c3) at least one fragrance whereby the compounds are present in a ratio by weight (a):(c1 +c2+c3) of from about 1:1,500,000:1 to about 1:1.
2. The composition of Claim 1 comprising the compounds in a ratio by weight (a):(c1 +c2+c3) of from about 1:500,000 to about 1:10.
3. The composition of Claim 1, wherein the at least one carrier (component b) is a solvent.
4. The composition of Claim 1, wherein the at least one carrier (component b) is a base for a candy, a tablet or a chewing gum.
5. The composition of Claim 1, comprising the compounds in amounts of from(a) 0,0001 to about 0.2 wt.-percent piperidine substituted imidazole compound;(b) about 50 to about 99.8 wt.-percent;(c) about 0.1 to about 1 wt.-percent at least one physiological cooling or warming agent (component c1, aroma or flavoring compound (component c2) and / or fragrance (component c3), on condition that the amounts add optionally together with further oral care additives 100 wt.-percent.The composition of Claim 1, wherein said physiological cooling compounds forming group (cl -1 ) are selected from the group consisting of:• Menthol• Menthol glyceryl acetal• Menthol glyceryl ketal• Menthol menthyl ether• Menthone glyceryl acetal• Menthone glyceryl ketal• Menthoxy-1,2-propandiol• Menthoxy-2-methyl-1,2-propanediol• Menthyl acetate• Menthyl ethylene glycol carbonate• Menthyl formiate• Menthyl glutamate• Menthyl glycerol carbonate• Menthyl hydroxy isobutyrate• Menthyl isobutyrate• Menthyl lactate• Menthyl malonate• Menthyl methyl ether• Menthyl N-ethyl oxamate• Menthyl propylene glycol carbonate• Menthyl pyroglutamate• Menthyl-(2-methoxy)acetate• Menthyl-(2-methoxyethoxy)acetate• Menthyl succinate• O-Menthyl succinic acid ester amide• O-Menthyl succinic acid ester-NN-(dimethyl)amide• Menthane carboxylic acid-N-(4-cyanophenyl)amide• Menthane carboxylic acid-N-(4-cyanomethylphenyl)amide• Menthane carboxylic acid-N-ethylamide (WS-3)• (WS-4)• N“-(menthane carbonyl) glycine ethylester (WS-5)• (1 R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1 -isopropyl)cyclohexane- carboxamide (WS-12)• (WS-14)• 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide (WS23)• Isopulegol acetate• p-Menthane-3,8-diol• Cubebol• 3-Methyl-2(1 -pyrrolidinyl)-2-cyclopentene-1 -one)• Tetrahydropyrimidine-2-one• N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide• [(1 R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] 2-(ethylamino)-2-oxo-acetate7. The composition of Claim 1, wherein said physiological warming compounds forming group (c1-2) are selected from the group consisting of:• vanillyl derivatives;• capsaicin;• allyl isothiocyanate;• gingerol;• 4-(l-menthoxymethyl)-2-phenyl-l;3-dioxolan;• 4-(l -menthoxymethyl)-2-(3';4'-dihydroxyphenyl)-l;3-dioxolan;• 4-(l-menthoxymethyl)-2- (2'-hydroxy-3 '-methoxyphenyl)-3-dioxolan;• 4-(l-menthoxymethyl)-2-(4'-methoxyphenyl)-3-dioxolan;• 4-(l-menthoxymethyl)-2-(3';4'methylenedioxyphenyl)-3 -dioxolan;• 4-(l-menthoxymethyl)-2-(3 '-methoxy-4'-hydroxyphenyl) -3 -dioxolan;• red pepper oil;• red pepper oleoresin;• ginger oleoresin;• nonylic acid vanillyl amide;• jambu oleoresin;• Zanthoxylum pieritum extract;• sanshool I;• sanshool II;• sanshoamide;• black pepper extract;• chavicine;• piperine; • spilanthol;8. The composition of Claim 1, wherein said flavors forming group (c2) are selected from the group consisting of:• 12-methyltridecanal;• acetaldehyde;• acetanisole;• acethylthiazole-2;• acethylthiazoline-2;• acetic acid;• acetyl methylcarbinol;• acetyl pyrazine-2;• acetyl pyridine-2;• allyl capronate;• allyl isothiocyanate;• amyl cinnamaldehyde-alpha;• anethole;• anisaldehyde-para;• anisic alcohol;• benzaldehyde;• benzyl acetate;• borneol-l;• butyl acetate;• butylidene phthalide-3;• butyric acid;• camphor;• caproic acid;• carvacrol;• carvomenthone;• carvon-d;• carvon-l;• carvylacetate-cis;• caryophyllene;• cineole-1;4;• cineole-1;8;• cinnamalcohol;• cinnamaldehyde;• cinnamyl acetate;• citral;• citronellal;• citronellol;• citronellyl acetate;• cresol• cuminaldehyde;• cyclopentadecanolide;• damascenone-alpha;• damascenone-beta;• damascone-alpha;• damascoe-beta;• decadienal-2;4;• decadienal-2;4;• decalactone delta;• decalacton gamma;• decanal;• dehydromenthofurolactone;• diallyl disulfide;• diethylpyrazine-2;3;• dihydroanethol;• dihydrocarvone;• dihydrocoumarin;• dihydroionone-beta;• dihydromenthofurolactone;• dihydronootkatone;• dimethyl lanthranilate;• dimethyl isopropyldithiazine;• dimethyl pyrazine;• dimethyl sulfide;• diphenyloxide;• divanilline;• d-menthol;• d-menthone;• d-menthyl acetate;• dodecalactone-delta;• dodecalactone-gamma;• epithiomenthan-1;8;• ethyl acetate;• ethyl butyrate;• ethyl capronate;• ethyl caprylate;• ethyl cinnamate;• ethyl isobutyrate;• ethyl isovaleria-nate;• ethyl lactate;• ethyl maltol;• ethyl methyl butyrate-2;• ethyl methyl thiopropionate;• ethyl phenol-4;• ethyl vanillin;• eugenol;• fenchol;• filbertone;• frambinone methyl ether;• frambinone;• furaneol;• furfurylthiol;• geraniol;• geranyl acetate;• geranyl isobutyrate;• guaiacol;• heliotropin;• heptalactone-gamma;• heptanone-2;• heptenal-Z-4;• hexalactone-gamma;• hexanal• hexanol;hexenol-E-2;• hexenol-Z-3;• hexenyl acetate-E-2;• hexenyl acetate-Z-3;• hexenyl capronate-Z-3;• hexyl acetate;• hexyl cinnamaldehyde-alpha;• hotrienol;• indole;• ionon-beta;• ionone-alpha;• isoamyl acetate;• isoamyl butyrate;• isoamyl isovaerianate;• isobutyl acetate;• isobutyl thiazole;• isobutylmethoxypyrazine• isobutyraldehyde;• isoeugenol;• Isomenthon;• isopropylmethoxypyrazine;• isopropylmethylpyrazine-2;4;• isopulegol;• isova-leraldehyde;• jasmine lactone;• jasmon cis;• ketoisophorone;limonene-d;• linalool oxide;• linalool-d;• linalool-l;• linalyl acetate;• l-menthol;• l-menthone;• l-menthyl acetate;• maltol;• massoilactone;• melonal;• menthadienyl acetate;• menthofurolactone;• menththiol-1;8;• methional;• methoxymethylpyrazine-2;3;• methyl anthranilate;• methyl butyl acetate-2;• methyl butyrate;• methyl cinnamate;• methyl dihydrojasmonate;• methyl furanthiol-2;3;• methyl jasmonate;• methyl salicylate;• methyl tetrahydrofuranthiol-2;3;• methyl thiobutyrate;• methyl thiohexyl acetate-1;3;• methylcyclopen-tenolone;• methylthiohexanol-1;3;• myrtenal;• naringin;• neo-menthol;• neral;• nerol;• nerylacetate;• nonadienal-2;4;• nonadienal-2;6;• nonalactone delta;• nonalactone gamma;• nonenal-E-2;• nonenal-Z-6;• nonenol-Z-6;• nootkatone;• octalactone gamma;• octalactone delta;• octanal• octenol- 1;3;• pellitorin;• pentenone-1;3;• pentyl acetate;• phenyl ethyl acetate;• phenyl ethyl alcohol;• phenyl acetaldehyde;• pinene-alpha;• pinene-beta;• piperitanate;• piperitone• prenyl thioacetate;• prenyl thiol;• reubenamine;• rose oxide;• rubescenamine;• sabinene hydrate;• scatole;• sotolone;• styrolyl acetate;• terpinenol-4;• terpineol;• thiohexanol-1;3;• thiohexyl acetate-1;3;• thiomenthanone-8;3;• thiopentanone-4;4;2;• thymol;• tridecatrienal;• trimethyl pyrazine;• undecadienal-2;4;• undecalactone-gamma and delta;• undecatriene;• vanillin;• vinyl guaiacol;• whisky lactone;The composition of Claim 1, wherein said fragrances forming group (c3) are selected from the group consisting of:• [(3,7-dimethyl-6-octenyl)-xy]-acetaldehyde,• 1 -(p-menthene-6(2)-yl)-1 -propanone,• 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde,• 10-undecen-1-al,• 10-undecen-1-ol,• 1 -decanal,• 1-dodecanal,• 1 -methyl-3-(4-methylpentyl)-3-cyclohexene-carboxyaldehyde,• 1 -methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1 -carboxaldehyde,• 1-nonanal,• 1 -octanal,• 1-octen-3-ol,• 1-p-menthene-q-carboxaldehyde,• 1 -undecanal,• 2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)-cyclopentanone,• 2,4,4,7-tetramethyl-oct-6-en-3-one,• 2,4,6-trimethyl-3-cyclohexene-l-carboxalde-hyde,• 2, 4-dimethyl-3-cyclohexen-1 -carboxaldehyde 4-methoxybenzaldehyde,• 2, 4-dimethyl-3-cyclohexen-1 -carboxyaldehyde,• 2,6,10-trimethyl-5,9-undecadienal,• 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al,• 2,6-dimethyl-5-heptenal;• 2,6-dimethylhept-5-en-1-al,• 2,6-dimethylheptan-2-ol,• 2,6-nonadienal,• 2-acetyl-3,3-di-methyl-norbornan,• 2-methyl decanal,• 2-methyl octanal,• 2-methyl undecanal,• 2-methyl-3-(4-tertbutyl)propanal,• 2-methyl-3-(isopropyl-phenyl)propanal,• 2-methyl-3-(para-methoxy-phenylpropanal),• 2-methyl-3-phenyl-2-propen-1 -al,• 2-methyl-4-(2,6,6-trimethyl-1 -cyclohexen-1 -yl)-2-butenal,• 2-methylbutanol,• 2-methylpentanol,• 2-phenoxyethanol,• 2-phenylpropan-1-al,• 2-phenylpropanol,• 2-tert-butycyclohexanol,• 3-(3,4-methylendioxy-phenyl)-2-methylpropan-1 -al,• 3-(3-isopropylphenyl)-butan-1-al,• 3-(4-ethylphenyl)-2,2-dimethylpropan-1 -al,• 3-(4-ethylphenyl)-2,2-dimethylpropanal,• 3-(4-isopropylphenyl)-2-methylpropan-1 -al,• 3-(4-methoxyphenyl)-2-methylpropanal,• 3-(4-tert-butylphenyl)-2-methyl-propanal,• 3-(4-tert-butylphenyl)-propanal,• 3,4-dimethoxybenzaldehyde,• 3,4-methylendioxybenzaldehyde,• 3,5,5-trimethylcyclohexanol,• 3,5,5-trimethylhexanal,• 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde,• 3,7-dimethyl-2-methylene-6-octenal,• 3,7-dimethyl-6-octen-1-al,• 3,7-dimethyloctan-1-al,• 3-ethoxy-4-hydroxybenzaldehyde,• 3-hexanol,• 3-methoxy-4-hydroxy-benzaldehyde,• 3-methyl-5-phenyl-1-pentanal,• 3-methyl-5-phenylpentanol,• 3-octanol,• 3-phenyl-2-hexylprop-2-enal,• 3-phenyl-2-pentylprop-2-en- 1 -al,• 3-phenyl-2-propenal,• 3-phenylprop-2-en-1-al,• 3-phenylpropanol,• 3-propyl-bicyclo[2.2.1]-hept-5-ene-2-carbaldehyde,• 4-(1-ethoxyvinyl)-3,3,5,5-tetramethyl cyclohexanone,• 4-(3)(4-methyl-3-pentenyl)-3-cyclohexen-carboxaldehyde,• 4-(4-hydroxy-3-methoxyphenyl)-2-butanone,• 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-l-carboxal-dehyde,• 4-(t ricyclo [5.2.1 ,0(2,6)]-decylidene-8)-butanal;• 4-damascol,• 4-heptenol,• 4-hydroxy acetophenone• 4-hydroxy-3-methoxybenzaldehyde,• 4-isopropyl benzyaldehyde,• 4-isopropyl cyclohexanol,• 4-methoxy benzaldehyde,• 4-methylphenyl acetaldehyde,• 4-tert-butyl cyclohexanol,• 5,9-dimethyl-4,8-decadienal,• 5-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,• 5-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,• 6,10-dimethyl-3-oxa-5,9-undecadien-1-al,• 6,6-dimethyl-2-norpinene-2-propionaldehyde,• 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone,• 6,8-dimethyl-2-nonanol,6-nonen-1 -ol,• 6-isopropyl-deca-hydro-2-naphtone,• 6-methoxyhexahydro-4,7-methanoindan-1 -carboxyaldehyde,• 6-methoxyhexahydro-4,7-methanoindan-2-carboxyaldehyde,• 7-hydroxy-3,7-dimethyl octanal,• 7-methoxy-3,7-dimethyloctan-1-al,• 9-decen-1-ol,• 9-decenal,• acetophenone,• adoxal,• allyl cyclohexylpropionate,• alphalonen,• ambroxan,• amylsalicylat,• anethol,• anisaldehyde,• benzaldehyde,• benzophenone,• benzyl acetate,• benzyl acetone,• benzyl alcohol,• benzyl salicylate,• benzylethyl ether,• bourgeonal,• buccoxime,• butyl lactate• butyl salicylate,• campher,• canthoxal,• carvone,• cassione,• celery cetone• chlorhydral,• cinnamalcohol,• cis- / trans-3,7-dimethyl-2,6-octadien-1-al,• cis-jasmon,• citral or its mixtures,• citronellal,• citronellol,• citronellyl oxyacetaldehyde,• cumal,• cyclamenaldehyde,• cyclohexyl salicylate,• cymal,• damarose,• damascenone,• decanol,• decyl aldehyde,• delphone,• dihydrojasmone,• dihydromyrcenol,• dihydrozimtaldehyde,• dihydro-fMonone,• dimethyl benzylcarbinol,• dimethyl benzylcarbinylacetate,• dimethyl heptanol,• dimethyl octanol,• dimethyl octenone,• dulcinyl• ethyl salicylate,• ethyl vanilin,• ethylmethylphenyl glycinate,• eugenol,• fenchone,• fleuramone,• flora lozon,• flora mat,• florhydral,• gelsone,• geraniol,• hedione,• helional,• heliotropin,• heptanol,• hexahydro-4, 7-methanoindan-1-carboxaldehyde,• hexahydro-8, 8-dimethyl-2-naphthaldehyde,• hexalone,• hexyl salicylat,• hydroxycitronellal,• isoborneol,• isodamascone,• isoeugenol,• isojasmone,• isopulegol,• jasmacyclatat,• koavon,• laurinaldehyde,• ligustral,• lilial citral,• lilial,• limonen,• linalool,• linalyl acetate,• livescon,• lyral,• m-cymene-7-carboxaldehyde,• melonal,• melusat,• menthol,• menthone,• methyl acetophenone,• methyl cedrenyl ketone,• methyl cedrylon,• methyl cedrylone,• methyl cyclocitrone,• methyl dihydrojasmonate,• methyl heptenone,• methyl lavender ketone,• methyl-dihydrojasmonate,• methylnonyl acetaldehyde,• methyl-|3-naphthyl ketone,• moschus indanone,• muscone,• myrtenol,• n-dodecanal,• neobutenone,• nerol,• n-hexanol,• nonanol,• n-undecanal,• octahydro-4, 7-methano-1 H-indenecarboxaldehyde;• octanal,• octanol,• o-methoxyzimtaldehyde,• orivone,• p-ethyl-a,a-dimethylhydrozimtaldehyde,• phenol,• phenoxyacetaldehyde;• phenoxyisobutyrate,• phenyl acetaldehyde,• phenyl salicylat,• phenylethyl acetate,• phenylethyl alcohol,• phenylpropyl alcohol• p-hydroxy phenylbutanone,• pinen• plicatone,• p-menthan-7-ol,• p-methoxy acetophenone,• p-methyl phenoxy acetaldehyde,• p-tert.-bucinal,• p-tert.-butyl cyclohexanone,• p-tert.-butyl cyclohexylacetate,• p-tolyl acetaldehyde;• styrallyl propionate,• tetrahydrogeraniol,• tetrahydrolinalool,• tetrameran,• thymol,• tonalid / moschus plus,• trans-2-cis-6-nonadienol,• trans-2-nonen-1-ol,• trans-2-octenol,• trans-4-decenal,• triplal,• undecanal,• undecanol,• undecylenraldehyde,• vanillin,• veloutone,• verdone,• a.-methyl-3,4-(methylenedioxy)-hydrocinnamaldehyde,• oc-damascone,• oc-methyl benzylalcohol,• oc-methyl-4-(l-methylethyl)benzene-acetaldehyde,• oc-methylphenylacetaldehyde,• ocn-Amylzimtaldehyde,• a-n-hexyl-cinnamaldehyde,• oc-terpineol,• |3-damascone,• |3-ionon,• p-terpineol,• y-methylionone,• S-damascone,10. The composition of Claim 1 representing a candy, a compressed tablet, a chewing gum, a toothpaste or a mouth wash.
11. A method for improving stability of an oral care composition encompassing the step of adding a working amount of at least one piperidine substituted imidazole compound of Claim 1 to said composition.
12. A method for increasing solubility of active ingredients in an oral care composition encompassing the step of adding a working amount of at least one piperidine substituted imidazole compound of Claim 1 to said composition.
13. A method for masking unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds encompassing the step of adding a working amount of adding a working amount of at least one piperidine substituted imidazole compound of Claim 1 to said composition.
14. The use of at least one piperidine substituted imidazole compound of Claim 1 for improving stability of an oral care composition.
15. The use of at least one piperidine substituted imidazole compound of Claim 1 for increasing solubility of active ingredients in an oral care composition.
16. The use of at least one piperidine substituted imidazole compound of Claim 1 for masking unpleasant flavors, particularly unpleasant flavors of fluorine derivatives and bitter compounds.
Citation Information
Patent Citations
medium WITH PHYSIOLOGICAL COOLING EFFECT
DE2608226A1
means with a physiological cooling effect and effective compounds suitable for these means
DE4226043A1
Anti-dandruff and anti-itch compositions containing a cooling sensate material and a cooling sensate enhancer
EP1332772A2
Pyrazole derivative, or pharmaceutically acceptable salt thereof
EP3315492A1
Smoking tobacco product and method of making the same
US3111127A