CN1703193A - Fragrance composition including an ionic liquid, its preparation and use - Google Patents
Fragrance composition including an ionic liquid, its preparation and use Download PDFInfo
- Publication number
- CN1703193A CN1703193A CN 200380101276 CN200380101276A CN1703193A CN 1703193 A CN1703193 A CN 1703193A CN 200380101276 CN200380101276 CN 200380101276 CN 200380101276 A CN200380101276 A CN 200380101276A CN 1703193 A CN1703193 A CN 1703193A
- Authority
- CN
- China
- Prior art keywords
- flavor compositions
- alkyl
- protection
- spice
- ionic liquid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
The invention relates to a fragrance composition, comprising at least one ionic fluid as fixative and production and use thereof. Said fragrance compositions have the advantage that the volatilisation of the basic aromatic components can be adjustably delayed with the ionic fluid as a polar solvent which has almost no partial pressure. The large choice of ionic fluids permits a precise adjustment of the volatilisation rate of the aromatic components. As the polarity of the ionic fluid can be varied over wide ranges by means of the structure of the cations and/or anions, the ionic fluid used as fixative can be precisely matched to the physico-chemical and/or olfactory requirements of the aromatic components.
Description
Technical field
The present invention relates to have flavor compositions, and relate to its preparation and purposes as at least a ionic liquid of fixastive.
Background technology
In the production of aromatic substance, what fixastive was explained is such material, it can make does not have the fragrance stability that is combined in the aromatic substance in the soap kind of spice to improve, and slows down and be fit to the volatilization of indivedual fragrance ingredients, and fragrance characteristic just can be quite lasting during volatilizing like this.As difficult volatilization of the material of fixastive great majority and boiling point height, itself can be savory or do not have fragrance.Between four kinds of main fixastive is distinguishing.Self fixastive is because therefore its lower volatility can keep its inherent abnormal smells from the patient for a long time and do not hinder other more volatile composition to discharge their abnormal smells from the patient (synthetic Moschus thing) during this period; Suppose pastil, because abnormal smells from the patient is more weak so be bonded on the crystalline solid with used as stabilizers or diffusant (diethylene glycol methyl ether); Stimulus object and basic thing thereof or synthetic analog (Ambra Grisea, castoreum, Moschus, Zibethum, muscone, some Macrolide materials, Fixative 404 etc.), they are natural animal class fixastive, as " catalyst " that discharge abnormal smells from the patient; " very " fixastive is by the fixed fixastive of absorption affinity (Ladanum fat extract, styracin, appropriate road face cream, Benzoinum, Rhizoma Iridis Tectori, robur lichen, opopanax etc.).Fixastive, usually be also referred to as the basis, effect based on be the vapour pressure that reduces aromatic substance, for example reduce vapour pressure by formation dipole, the hydrogen bridge of connection, adsorption, formation azeotropic mixture, although some other effects comprise the physiological role of skin and have also produced the sensation of influence property (R mpp Lexikon Chemie-Version2.0, Stuttgart/New York:Georg Thieme Verlag 1999).
Change though producing new abnormal smells from the patient, also just using new artificial fragrance or fragrance ingredient thus, but still need find the novel substance that is suitable for specific fragrance ingredient or fragrance ingredient compositions as fixastive.The quantity that the quantity that is suitable for being fit to chemical compound as fixastive increases rapidly far away from fragrance ingredient and fragrance or flavor compositions.
Summary of the invention
Therefore our purpose provides and can control the fixastive that fragrance or fragrance component evaporate and/or discharge from flavor compositions in the target mode, this fixastive should be various, could be fit to the different used aromatic substances or the requirement of spice like this, especially with new aromatic substance and the spice that produces of simple mode.
Surprisingly, we have found that ionic liquid is suitable for unexpectedly as the fixastive in the flavor compositions, because in fact they do not have vapour pressure, and along with used cation and/or anionic structure difference, their polarity can be easily regulated in the larger context, so just specific spice can be fit to.
Therefore, the invention provides a kind of flavor compositions with fixastive, it is characterized in that, this flavor compositions has at least a ionic liquid as fixastive.
Equally, the invention provides a kind of method for preparing flavor compositions of the present invention, it comprises fragrance component and ionic liquid powerful mixing.
In addition, the invention provides the purposes of flavor compositions in various products day by day as described in the present invention, for example senior spice (Fcinparf ü me), watch box compositions (K rperpflegemittel), cosmetics, for example soap, deodorizer reach more materials, detergent spice, fabric softener spice or cover industrial abnormal smells from the patient and the preparation in used spice, have the product day by day of flavor compositions as described herein in addition.
The advantage of flavor compositions is that they can make with simple method as described herein.Especially, fixastive can be formulated in the spice or fragrance ingredient of use with simple method.Use ionic liquid that advantage is also arranged, although very low its viscosity of the vapour pressure of that ionic liquid is also relatively low.For as for example diethylene glycol methyl ether of compound that routinizes of fixastive, the low-vapor pressure of most of materials all joins is being with high viscosity, and therefore, the machinability of this based composition is just weakened and/or need carry out corresponding dilution.
By following examples the present invention is described, but this also should not be construed as limiting the present invention.
The specific embodiment
The flavor compositions that has fixastive as described in the present invention, its noticeable place are that it has at least a ionic liquid as fixastive.Preferably, this flavor compositions has by base oil, and 0.1% weight is to the ionic liquid of 20% weight, and preferred especially 0.5% weight is to the ionic liquid of 10% weight, the ionic liquid of the most preferred 1 to 5% weight.
Concerning flavor compositions, below classification is commonly used in the spice:
Wherein base oil should be understood that the meaning of true aromatic substance or aromatic oil.
Usually, ionic liquid is understood that the special liquid of being made up of ion.In the division of salt melt conventional term, salt melt Gao Rong, high sticking and be to have very much corrosive medium as a rule normally wherein, ionic liquid at low temperatures (＜100 ℃) be liquid and have low relatively viscosity.Although just known ionic liquid since 1914, they only are widely studied as the catalyst in solvent and/or the organic synthesis that (K.R.Seddon is in J.Chem.Technol.Biotechnol.68 (1997), 351-356 in the period of nearly 10; T.Welton is at Chem.Rev.99 (1999), 2071-2083; J.D.Holbrey, K.R.Seddon is at Clean Products and Processesl (1999) 223-236; P.Wasserscheid, W.Keim are in Angew.Chem.112 (2000), and 3926-3945 and R.Sheldon are at Chem.Comm. (2001), the review article among the 2399-2407).Preferred ionic liquid has the fusing point less than 80 ℃.The most particularly preferred ionic liquid can at room temperature be present in the liquid phase.
With regard to ionic liquid, flavor compositions preferably has at least a cationic salt shown in the following array structure 1 to 8 that has,
Wherein, R1, R2, R3, R4, R5 and R6 are identical or different, they are hydrogen, have the straight or branched aliphatic hydrocarbyl of 1 to 20 carbon atom, have 5 to 30 carbon atoms the cyclic aliphatic alkyl, have 6 to 30 carbon atoms aromatic hydrocarbyl, have 7 to 40 carbon atoms alkaryl, have the straight or branched aliphatic hydrocarbyl of 2 to 20 carbon atoms, it is by one or more hetero atoms (oxygen, NH, NCH
3) separate, have the straight or branched aliphatic hydrocarbyl of 2 to 20 carbon atoms, its by one or more be selected from group-O-C (O)-,-(O) C-O-,-NH-C (O)-,-(O) C-NH-,-(CH
3) N-C (O)-,-(O) C-N (CH
3)-,-S (O)
2-O-,-O-S (O)
2-,-S (O)
2-NH-,-NH-S (O)
2-,-S (O)
2-N (CH
3)-,-N (CH
3)-S (O)
2-functional group (Funktionalit ten) separate terminal quilt-OH ,-NH
2,-N (H) CH
3Functionalized straight or branched aliphatic hydrocarbyl with 1 to 20 carbon atom or have block or disordered structure as-(R
7-O)
n-R
8Shown polyethers, wherein R
7Be the straight or branched alkyl that comprises 2 to 4 carbon atoms, n=1 to 30, R
8Be hydrogen, have 1 to 20 carbon atom the straight or branched aliphatic hydrocarbyl, have 5 to 30 carbon atoms the cyclic aliphatic alkyl, have 6 to 30 carbon atoms aromatic hydrocarbyl, have 7 to 40 carbon atoms alkaryl or-C (O)-R
9Group, wherein R
9Be straight or branched aliphatic hydrocarbyl, cyclic aliphatic alkyl, the aromatic hydrocarbyl with 1 to 20 carbon atom, alkaryl with 7 to 40 carbon atoms with 6 to 30 carbon atoms with 5 to 30 carbon atoms; And anion, it is selected from halogenide, for example chloride, bromide and iodide, preferably iodide; Phosphate radical, halophosphoric acid root, preferred hexafluoro-phosphate radical; Alkyl phosphoric acid root, nitrate anion, sulfate radical, bisulfate ion, alkyl sulfate, preferred octyl group sulfate radical; Aromatic sulfuric acid root, perfluorinated alkyl-and aromatic sulfuric acid root, sulfonate radical, alkyl azochlorosulfonate, aryl sulfonic acid root, perfluorinated alkyl-and aryl sulfonic acid root, preferred trifluoromethanesulfonic acid root (triflate); Perchlorate, tetrachloro aluminate, tetrafluoroborate, boron alkyl acid group, preferred B (C
2H
5)
3C
6H
13 -Tosylate, glucide root (saccharinate), alkyl carboxylic acid root and two (perfluoroalkyl group sulfonyl) amide anion, preferred two (trifyl) amide anion; The perhaps mixture of multiple these salt.
In the preferred embodiment of flavor compositions as described herein, ionic liquid has not halogen-containing anion, it is selected from phosphate radical, alkyl phosphoric acid root, nitrate anion, sulfate radical, alkyl sulfate, aromatic sulfuric acid root, sulfonate radical, alkyl azochlorosulfonate, aryl sulfonic acid root, boron alkyl acid group, tosylate, glucide acid group and alkyl carboxylic acid root described anion, especially preferred is alkyl sulfate, particularly octyl group sulfate radical, and tosylate.
Flavor compositions especially preferably has at least one and has cationic salt as ionic liquid: described cation is selected from imidazol ion, pyridinium ion, ammonium ion or the phosphonium ion of following formula structure:
R and R '=H wherein, they are identical or different replacement or unsubstituted alkyl, alkylene or aryl, additional conditions are that R and R ' have identical or different implication.
Particularly preferred ionic liquid is for example 1-ethyl-3-Methylimidazole. toluene fulfonate, trioctylammonium octyl sulfate, 1,3-methylimidazole octyl sulfate, two (trifluoromethanesulfonic acid base) amide of 1-ethyl-3-methyl-imidazoles, the nor-Adeps Bovis seu Bubali of 1-methyl-2-(nortallow)-3-Adeps Bovis seu Bubali acylamino-ethyl-imidazoles Methylsulfate or the nor-oil base of 1-methyl-2-(noroleyl)-3-oil base acylamino-ethyl imidazol(e) Methylsulfate.
If flavor compositions has a kind of ionic liquid, this liquid has the salt of addressing more than one or more, will be favourable so.At this, cation can be different with anion.The ionic liquid of flavor compositions especially preferably has different aniones.By using different aniones and/or cation, its character can be with the mode of the best and other composition coupling, especially fragrance ingredient of flavor compositions.
The preparation of ionic liquid generally is known, and it can be by method preparation, the especially S.Saba of for example record of document, A.Brescia, M.Kaloustian, TetrahedronLetters 32 (38) (1991), 5031-5034, EP 1 072 654 and EP 1 178 106.In addition, ionic liquid also can commercially can obtain.Like this, for example 1,3-methylimidazole Methylsulfate, 1-butyl-3-Methylimidazole. Methylsulfate, 1-ethyl-3-Methylimidazole. toluene fulfonate, 1-ethyl-2,3-methylimidazole toluene fulfonate and ECOENG
TM, these not halogen-containing salt just can be from Solvent Innovation GmbH, Alarichstr.14-16, and 50679 K ln, Germany obtains.
Depend on the planned use of flavor compositions, the same with other all composition, ionic liquid also will be through screening, to get rid of the healthy or ecological material that adverse effect is arranged to people, nature and environment.Like this, the flavor compositions that directly contacts with human organism for example spice or flavorant compositions must be the totally nontoxic effect, and for directly contacting for example room deodorizer of the flavor compositions that is safe from danger fully with the mankind or animal organisms, then can be lower to the requirement of flavor compositions.
Yet,,, will be favourable so if in flavor compositions, there is chemical compound ionic liquid especially with microbicidel characteristic for some selectivity application products.If flavor compositions is to be used to suppress the abnormal smells from the patient that formed by microorganism, so owing to have this chemical compound energy killing microorganisms of microbicidel characteristic, the new formation of bad smell just can be suppressed or delay it at least and form, and therefore this chemical compound with microbicidel character is gratifying all the time.Application products has for example deodorizer or sufficient spray.
Beyond the deionization liquid, flavor compositions can also have other fixastive as described in the present invention, and it is selected from known self fixastive, supposition pastil, stimulant and/or " very " fixastive.
Flavor compositions can also have stroma ground substance.This stroma ground substance can be solid-state or liquid.Suitable liquid matrix material has for example organic solvent, for example alcohol or ether or water or its mixture.Especially for the perfume application products, flavor compositions can have alcohol, and especially highly purified ethanol is as liquid matrix material (solvent).The solid state substrate material can be solid salt sodium chloride, sodium sulfate, detergent additive citrate or polycarboxylate, soap, polymer for example bentonite, montorillonite clay or organically-modified sheet silicate (being commonly referred to dynamo-electric shape silicate), zeolite or a cyclodextrin of cellulose, sheet silicate (Schichtsilikate) for example for example for example for example.If if flavor compositions is used with solid form or aromatic substance only contacts with water and could discharge, these materials need all the time so.
Flavor compositions can have a kind of commonly used, known and conventional chemical compound as fragrance thing, spice, fragrance component or fragrance ingredient as described in the present invention.Especially, flavor compositions can have natural, with natural identical, semi-synthetic and/or complete synthesis spice or fragrance thing as spice or fragrance thing.Such composition is known fully.For example at Flavor andFragrance Meterials, Worldwide Ref.List (the 14th edition), Wheaton:Allured 1987; Frosch etc. (ed.), Fragrances:Beneficial andAdverse Effects, Berlin:Springer 1997; Hager (the 5th edition) 1,152,198 ff.:Kirk-Othmer (the 4th edition) 18,171-201; R mpp LexikonNaturstoffe, p.552f., Ullmann (the 4th edition) 20,199-287; (the 5th edition) A11,141-250, Vollmer and Franz, Chemie in Bad u.K ü che, pp.128-140, Stuttgart:Thieme 1991, Calkin and Jellinek, Parfumery-Practice and Principles, New York:Wiley 1994; Kirk-Othmer (the 4th edition) 17,594-603; 18,171-201; Ullmann (the 4th edition) 17,645-650; 20,199-287; (the 5th edition) A 11,141-250; Umbach (ed.), Kosmetik, the 2nd edition, 343-360, the 408-417 page or leaf, Stuttgart:Thieme 1995; Vollmer and Franz, Chemische Produkte im Alltag, 129-142,433-449 page or leaf, Stuttgart:Thieme 1985. provided can as fragrant for and/or the summary and the background information of the chemical compound of fragrance thing.
It is the general introduction of key word that R mpp Lexikon Chemie-Version 2.0, Stuttgart/New York:Georg Thieme Verlag 1999 have provided with various spice, spice (Parf ü ms), spice (Duftstoffe), fixastive and these different terms of fragrance thing.Give at this and typically to generate breaking down of spice (Parf ü m Komposition) compositions (for example flavor compositions), if it has ionic liquid as fixastive, it drops within the theme of the present invention too so.The structure of flavor compositions (Parf ü m Komposition) is divided into:
1. top composition (mainly, the highest, inherent fragrance), the volatile spice of main brand-new characteristic;
2. inter-level (fragrance, main body, essence, essence composition, main body), the medium volatilization spice of common colored characteristic;
3. basis (basic, back fragrant), the low volatility spice of decision spice fundamental characteristics (leading abnormal smells from the patient).
Thus, basis is fixastive normally also, and it has improved the sticking and property of volatile flavour and adhesive and has stablized perfume compositions.Use adjuvant, so top, centre and basis just can more closely be linked together, and perfume compositions also can more successfully form.
Deionization liquid is as outside the odoriferous material, is present in chemical compound in the flavor compositions or mixture and for example also comprises following chemical compound or product from Harmann and Reimer company.
Abriceine, Acetanisol dest., Acetanisol krist., the purified petroleum benzin ethyl ketone, Agarwood D50092NS, Agrumen aldehyde 6947L, Agrumex HC, Agrumex LC, Agrumovert 10897C/L, aldehyde C6 nat., aldehyde C11 MOA, aldehyde C12 MNA, name is called aldehyde C14 usually, usually be called aldehyde C16, usually be called aldehyde C18/Abricolin, alcohol C6 nat., alcohol C8, alcohol C9, alcohol C10, alcohol C12, the Allinat/ allyl isothiocyanate, Allinat/ allyl isothiocyanate (stab.), allyl hexanoate, allyl hexanoate kosher, allyl cyclohexyl propionate, allyl heptanoate, the phenoxyethanoic acid allyl ester, Amarocit, Ambre 83LN DB10028, Ambrebois D50407, Ambrettia C, musk lactone, Ambrinol S, Ambroxid krist., Ananas Coeur D50214, 21/22 ℃ of anethole NPU, 21.5 ℃ of anethole supra, pure anisaldehyde, anise alcohol, anisole, anisyl acetate, apple 74180C PM, Apriconia 28855P extra PM, Baldrian Identoil B, basil Synthessence, bay Identoil, benzalacetone, benzaldehyde, benzaldehyde dd, Benzophenone Krist., benzyl acetate, benzylacetone, benzylalcohol dd, benzylalcohol FR, Ergol H﹠R, Ergol M, the cinnamic acid benzyl ester, benzyl formate, benzyl propionate, benzyl salicylate, colourless bergamot Identoil, Africa bergamot Synthessence, blackberry, blueberry D50260E, Bois de Cachemire D50008, Bois Doux 78008SP PM, Boisanol, Boronal, butyric acid nat., butyl butyrate, cocoa and chocolate D50546B, cajeputtree Identoil, Calmus Synthessence Asaron-free, cananga oil Identoil, capric acid nat., caproic acid nat., the caramel acetate, cardamom R Identoil, cardamom Synthessence, Chinese cassia tree Identoil, Chinese cassia tree Identoil B dunkel, currant D50060B, cdear leaf Identoil, parachloroacetophenone, chrysanthemum, cinnamyl acetate, citral extra, lemon R, lemon Synthessence FF, lemongrass Identoil, Citronell Identoil, the tiglic acid citronellyl acrylate, lemonile (Citronitril), CitrowanilB, Citrozone D50620B, lemon oil aldehyde (Citrylal), lemon oil aldehyde E, Clarifruit D50757, bugle alkali (Clarion Base) D50774, Corapan TQ, coriander Identoil, Corps 1729, Corps 98N DB10025, Corps Racine VS, the banksia rose (Costus) Synthessence, coumarone, cumin Synthessence, Cyprus Identoil, Datilat, gamma decalactone nat., beta Decalyl acetate, diacetyl nat., Dibenzosuberone, benzyl ether, diethyl phthalate (DEP), dihydrocoumarin, the o-amino benzoyl dimethyl phthalate, dimethylbenzyl carbinyl butyrate, dimethylsulphide nat., phenylate, noble fir needle Identoil, noble fir needle Identoil B, Oak Tree liver moss resin D50342, strawberry D50026C, acetic acid nat., tarragon Identoil, the ethyoxyl furanone, ethyl 2-methylbutyrate nat., ethyl hexanoate non-kosher, 2-Methyl Butyric Acid ethyl ester, ethyl acetate nat., ethyl acetoacetate, ethyl benzoate, ethyl butyrate, ethyl butyrate nat., ethyl hexanoate, ethyl hexanoate nat., ethyl caprilate, ethyl caprilate nat., ethyl cinnamate, Ethyl formate, cognac oil, ethyl isovalerate, acetic acid ethyl phenyl ester, ethyl propionate, salethyl, ammonium tree brain, eucalyptus oil globule (Globulus) BP, eugenol, eugenol methyl ether, Farenal, fennel oil techn., Feuilles de Tomate 79569PM, the green 8001S of dragon spruce, needles Leaves in Picea Identoil Bsib., needles Leaves in Picea Identoil sib., Filbertone G, Canada balsam DM, Fleur de Cassis SBU PM, Floropal, Florophyll 10183, Fragolane, Framboson 10583F, Frutinat, galbanum Synthessence, galbanum synthetic resin (Synthresin) B, Africa fish pelargonium Identoil, fish pelargonium Identoil Bourbon, Geranyl tiglint, Globalid 100%, Globanone 50%DEP, Globanone 50%DPG, Globanone 50%IPM, uva D50075N, uva Identoil D61286G, green honeydew melon D50315, guava 10875N, strawflower Synthessence, Herbaflorat, hexyl acetate, hexyl acetate nat., 1-Hexyl salicylate, hydrogenation lemonile (Hydrocitronitril), Indian Spice 10898, Indoflor H﹠R krist., indoles FF, ginger oil spez.D40393S, pure irisone 100%, iris synthetic rubber H﹠R, Irolene P, isoamyl acetate G, isoamyl acetate nat., isoamyl butyrate, isoamyl butyrate nat., isoamyl isobutyrate nat., iso-amyl iso-valeriate, Isoananat, isobornyl acetate, isobutyric acid nat., isobutyl acetate nat., isobutyl quinoline, isobutyl quinoline 54, the isoeugenol methyl ether, Isotabac naturelle LN DB10038, Jasmaprunat, camomile Identoil is blue, camomile r m.Synthessence, pine needle Identoil, pine needle Identoil B, pine needle Identoil B P, kiwi D50195PM, methyl para-cresol, lactic acid jasmone (Lactojasmon), Lavandin Identoil 30/32%, Lavandin Identoil France type 30/32%, Lavandin Provence D50817, lavender Identoil Mt type, Blanc 40/42%, lavender oil Mt type, Blanc 40/42%, Leguminal, pure limonene d, the sweet certain kind of berries D50398N of sieve PM, laurel D50286, mace oil extra, Macrolide、
Macrolide
supra, Mandranol, Magnolan, Majantol, Mandaril, Manderine Synthessence, mango D50436PM, Maracuja D50042E PM, Marjoliane N DB10018, Mayciane N DB10023, German lemon balm Identoil by name, menthol D dist., menthol liquid, menthol rac., menthol rac.PH, menthol-1 dest., in conjunction with menthol-1 H﹠R, the peppermint cerebrol, menthones-1/-isomenthone-d, acetic acid base ester-1, Metaxa D50247C, 2,3-ethyl pyrazine, 2-methylbutanoic acid methyl esters, melilotal, Anthranilate, methyl benzoate H﹠R, methyl benzoate techn. is pure, methyl beta naphthonone krist., 2-Methyl Butyric Acid nat., methyl cinnamate, acetic acid aminomethyl phenyl ester, gaultherolin, the alpha methyl cinnamic acid, Miel Blanc N DB10024, amber seed Synthessence, Mugetanol, Mugofleur D50444PM, Salvia japonica Identoil, Salvia japonica Identoil B, lilac Identoil, clove leaf Identoil dunkel, the entf. of clove leaf oil, the new nonyl ester of acetic acid, neroli oil Identoil, nerol oxide Yara Yara krist., neroli oil 4663, frankincense synthetic resin, tangerine Identoil TSA, tangerine oil spez.D40393P, wild marjoram tail Identoil, Oryclon extra, Oryclon spezial, Osmanthia 353, Ozonil, Palisandal, Palisandin, Palmarosa Synthessence, Pastinak Synthessence, Pogostemon cablin Synthessence N, patchouli oil dentf.DM, pears D50313A PM, peru balsam Identoil, peru balsam kstl.H﹠R, orange folic acid orange Synthessence, orange leaf Identoil R, peach D40110PM, plum D50424, Phenirat, Phenoxyethanol/Arosol, phenylacetaldehyde 100%, phenylacetaldehyde dimethyl alcohol acetal, phenylethyl acetate, purified petroleum benzin ethanol, phenylethyl cinnamate krist., phenethyl isobutyrate,phenylethyl isobutyrate, acetic acid phenethyl phenylester, phenylpropanol, dried green pepper tree Identoil, Poivre Coeur H﹠R PM, Poivron N DB10029, acetic acid isoprene ester, salicylic acid isoprene ester, Profarnesal, Projasmone P, propionic acid nat., propyl acetate nat., ursolic acid N DB10027, Pyroprunat, educate prosperous shore Alkaloid (Rain Forest) D50339C PM, Resedafol, Rosaphen, rose Booster D50221A, rose F50048R PG, rosemary, Xue MingRosma rinus officinalis Identoil, Spain rosemary, Xue MingRosma rinus officinalis Identoil, dalbergia wood bras.Identoil, Salvia japonica Identoil span., Salvia japonica Identoil span., santal S.E.A.D50820, Sandel 80, Sandel extra, Sandel Forte, Sandel H﹠R, Sandel H﹠R super, Sandel SP, Sandel Typ Ostind, Sandelholz Typ Ostind, Sandolen H﹠R, spike oil (Spik) Identoil, storax Identoil D50186, phenylethyl acetate (Styrollyl acetate), sweet amber D50807, the fragrant H﹠R D50799 of tobacco, Teatree D50780A, thyme Identoil, the red Identoil of thyme, thyme synthesizes absolute oil (Synthabsolue), thymol dest., thymol krist.H﹠R, Tonca synthetic resin, vanillic aldehyde nat., France type Verbena officinalis Identoil, Verdeflora D50375D, Verdural F, Vertocitral, Vertocitral C, Vertosine, cus-cus Identoil J, needle juniper fruit Identoil 10900, needle juniper fruit Synthessence, the fragrant 6103CB HG of willow, wintergreen, the blue 10372MT of clothing, the blue Identoil Bourbon of the blue clothing of clothing I, the blue Identoil Bourbon of the blue clothing of clothing II, the blue Identoil Bourbon of the blue clothing of clothing III, cinnamic acid, cinnamic acid nat., cinnamyl alcohol, basyleaves Identoil and/or cassia Identoil.
Self-explantoryly be, flavor compositions can comprise these chemical compounds as described in the present invention, and especially as spice, it is suitable as fragrance thing, fragrance or spice, or as solid-state or liquid matrix material, it provides by other manufacturer or is provided by the material that nature exists.
Except that mentioned component,, will be favourable so if compositions further has additive for example emulsion adjuvant, antiseptic or analog as described in the present invention.
Flavor compositions is preferably by method preparation of the present invention as described in the present invention.Its noticeable place is, concerning preparing as described in the present invention flavor compositions, and near a kind of fragrance/flavor or base oil and at least a ionic liquid powerful mixing.If before powerful mixing, spice and/or ionic liquid are mixed with solid-state or liquid matrix material and/or additive, will be favourable so.
Base oil by being grouped into more than a kind of fragrant virtue flavor, at room temperature being operated through cold mixing usually and is carried out cold mixing, with the side reaction of avoiding not expecting with the flavouring agent generation under its most of situation.This base oil can directly mix with ionic liquid.The mixing of base oil and ionic liquid is also preferred at room temperature or under the highest 35 ℃ temperature to be carried out through the cold mixing operation.If a kind of composition, promptly spice or ionic liquid are solid forms, they preferably are dissolved in the solvent earlier so, at high temperature carry out if desired, mix with liquid spice or base oil the cooling back so, and they are chosen wantonly and can contain ionic liquid so.
Or the material that viscosity is high low concerning miscibility, it is favourable using (shearforces) (the rotor stator system the is Turrax system for example) stirring system with high shear force.If solids mixes therein, add liquid so earlier, and then in suitable dispersal unit, mix.
Flavor compositions can be used as spice, soap additive, deodorant addtives and analog as described in the present invention.Especially, as described in the present invention flavor compositions can be used to produce spice, soap, deodorizer, hair-treatment composition, watch box compositions, detergent and cleaning agent, household supplies, room air freshener and indoor spraying, food and luxury goods, essence and condiment composition or smoke agent.By the product that flavor compositions of the present invention can obtain having these compositionss at an easy rate, especially above-mentioned product day by day.Such product can be for example senior spice, watch box compositions, cosmetics, detergent spice, fabric softener spice or the spice of covering industrial abnormal smells from the patient.
The specific embodiment
Embodiment:
According to three kinds of flavor compositions of formulation of embodiment 1-3 record, (I) all arranged and do not have (Ia) fixastive in every kind:
Embodiment 1:
The composition of I Ia chypre
300 300 Oleum menthae
80?????80????????Mousee?de?Chene?absol.
The blue clothing orchid of 60 60 clothing
15 15 jasmine absol.
15????????15????????Rose?de?Mai?absol.
20????????20????????Dianthine(Firmenich)
50????????50????????Iralia
60????????60????????Irrozol
35 35 propylbenzene ethylhexanals
15 15 vanillin
70 70 vetiver oils
50????????50????????Oppononax
100 100 sunflower Oleum sesami
20????????20????????Sandel?oil?O.I.
40 40 patchouli oils
30 30 dihydrocoumarones
5 40 rings, penta decanolid
35 0 1.3-dimethyl-imidazoles Methylsulfate
1,000 1000 weight portions
Embodiment 2:
I Ia Moschus substrate
280 280 synthetic Flos Rosae Rugosaes
80????????80????????Rose?absol.
100 100 jasmine liqu.S.A.
60 60 synthetic jasmines
60 60 Oleum Pelargonii Graveolentiss
125 125 Oleum menthae
25 25 patchouli oils
50 50 synthetic Polianthes tuberosa L.s
25 25 Polianthes tuberosa L. absol.
60 60 Oleum Cinnamomis
40 40 Benzoinum Siam resinoids
25 25 synthetic Zibethum
45 70 cyclopentadecanones
25 0 1-ethyl-3-Methylimidazole. toluene fulfonate
1,000 1000 weight portions
Embodiment 3:
I Ia Flos Rosae Rugosae compositions
55 Oleum Pelargonii Graveolentis Bourbon
10 10 phenethyl isoamyl oxides
20 20 hyacinthin
20 20 citrals
30 30 dihydro Flos Rosae Rugosae oxides
40 40 phenylethyl acetates
80 80 phenethanol
50 50 geranyl acetates
250 280 geraniol
450 450 citronellols
10 15 ethyl vanillins
35 0 1-butyl-3-Methylimidazole. Methylsulfate
1000??????1000
Embodiment 4:
In order to determine the adhesion intensity of compositions, to be sprayed onto on 3 * 3 centimetres the cotton fiber as described each compositions (embodiment variant 1) that comprises a kind of ionic liquid as described herein of embodiment 1 to 3, compare experiment with the correspondent composition that does not have ionic liquid, determine adhesion intensity with the abnormal smells from the patient experiment.Find that all compositionss with ionic liquid are all significantly big than the correspondent composition adhesion intensity that does not have ionic liquid.This means that in having the compositions of ionic liquid its fragrance that can perceive is more permanent than the compositions that does not have ionic liquid.
Claims (17)
1. flavor compositions, it has fixastive, it is characterized in that, and flavor compositions has at least a ionic liquid as fixastive.
2. the flavor compositions of asking for protection as claim 1, wherein compositions has by base oil, and 0.1% weight is to the ionic liquid of 20% weight.
3. the flavor compositions of asking for protection as claim 1 or 2, wherein compositions has by the basis, and 0.5% weight is to the ionic liquid of 10% weight.
4. the flavor compositions of asking for protection as claim 1 to 3, wherein ionic liquid is the cationic salt with following structure,
Wherein, R1, R2, R3, R4, R5 and R6 are identical or different, they are hydrogen, have the straight or branched aliphatic hydrocarbyl of 1 to 20 carbon atom, have 5 to 30 carbon atoms the cyclic aliphatic alkyl, have 6 to 30 carbon atoms aromatic hydrocarbyl, have 7 to 40 carbon atoms alkaryl, have the straight or branched aliphatic hydrocarbyl of 2 to 20 carbon atoms, it is by one or more hetero atoms (oxygen, NH, NCH
3) separate, have the straight or branched aliphatic hydrocarbyl of 2 to 20 carbon atoms, its by one or more be selected from group-O-C (O)-,-(O) C-O-,-NH-C (O)-,-(O) C-NH-,-(CH
3) N-C (O)-,-(O) C-N (CH
3)-,-S (O)
2-O-,-O-S (O)
2-,-S (O)
2-NH-,-NH-S (O)
2-,-S (O)
2-N (CH
3)-,-N (CH
3)-S (O)
2-functional group separate terminal quilt-OH ,-NH
2,-N (H) CH
3Functionalized straight or branched aliphatic hydrocarbyl with 1 to 20 carbon atom or have block-wise or disordered structure as-(R
7-O)
n-R
8Shown polyethers, wherein R
7Be the straight or branched alkyl that comprises 2 to 4 carbon atoms, n=1 to 30, R
8Be hydrogen, have 1 to 20 carbon atom the straight or branched aliphatic hydrocarbyl, have 5 to 30 carbon atoms the cyclic aliphatic alkyl, have 6 to 30 carbon atoms aromatic hydrocarbyl, have 7 to 40 carbon atoms alkaryl or-C (O)-R
9Group, wherein R
9Be straight or branched aliphatic hydrocarbyl, cyclic aliphatic alkyl, the aromatic hydrocarbyl with 1 to 20 carbon atom, alkaryl with 7 to 40 carbon atoms with 6 to 30 carbon atoms with 5 to 30 carbon atoms; And a kind of anion; it is selected from halogenide, phosphate radical, halophosphoric acid root, alkyl phosphoric acid root, nitrate anion, sulfate radical, bisulfate ion, alkyl sulfate, aromatic sulfuric acid root, perfluorinated alkyl-and aromatic sulfuric acid root, sulfonate radical, alkyl azochlorosulfonate, aryl sulfonic acid root, perfluorinated alkyl-and aryl sulfonic acid root, perchlorate, tetrachloro aluminate, tetrafluoroborate, boron alkyl acid group, tosylate, glucide acid group, alkyl carboxylic acid root and two (perfluoroalkyl group sulfonyl) amide anion, or the mixture of multiple these salt.
5. the flavor compositions of asking for protection one of at least as claim 1 to 4 wherein uses as ionic liquid to have cationic salt, and it is selected from the imidazol ion shown in the following array structure, pyridinium ion, ammonium ion or phosphonium ion described cation:
R and R '=H wherein, they are identical or different replacement or unsubstituted alkyl, alkylene or aryl, additional conditions are that R and R ' have identical or different implication.
6. the flavor compositions of asking for protection one of at least as claim 1 to 5; wherein ionic liquid has not halogen-containing anion, and described anion is selected from phosphate radical, alkyl phosphoric acid root, nitrate anion, sulfate radical, alkyl sulfate, aromatic sulfuric acid root, sulfonate radical, alkyl azochlorosulfonate, aryl sulfonic acid root, boron alkyl acid group, tosylate, glucide acid group and alkyl carboxylic acid root.
7. the flavor compositions of asking for protection one of at least as claim 1 to 6, wherein the ionic liquid of flavor compositions has different aniones.
8. the flavor compositions of asking for protection one of at least as claim 1 to 7, wherein flavor compositions has microbicidel character.
9. the flavor compositions of asking for protection one of at least as claim 1 to 8, wherein, except that having at least a ionic liquid, it also has fixastive, and it is selected from self fixastive, supposition pastil, stimulus object and/or " very " fixastive.
10. the flavor compositions of asking for protection one of at least as claim 1 to 9, it has the alcohol as solvent.
11. as the flavor compositions that claim 1 to 10 is asked for protection one of at least, its have as spice natural, with natural identical, semi-synthetic and/or complete synthesis spice.
12. as the flavor compositions that claim 1 to 11 is asked for protection one of at least, it has antiseptic.
13. the method for the flavor compositions that production such as claim 1 to 12 are asked for protection one of at least is wherein with at least a spice and at least a ionic liquid powerful mixing.
14. as the method that claim 13 is asked for protection, wherein the mixing of spice and ionic liquid is at room temperature cold carries out.
15. the flavor compositions of asking for protection as one of claim 1 to 12 is as senior spice, watch box compositions, cosmetics, detergent spice, fabric softener spice or as the purposes of covering the spice of industrial abnormal smells from the patient.
16. a product, it has as one of any flavor compositions of asking for protection of claim 1 to 12.
17. as the product that claim 16 is asked for protection, wherein product is senior spice, watch box compositions, cosmetics, detergent spice, fabric softener spice or the pastil of covering industrial abnormal smells from the patient.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10247514 | 2002-10-11 | ||
| DE10247514.8 | 2002-10-11 | ||
| DE10337579.1 | 2003-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1703193A true CN1703193A (en) | 2005-11-30 |
Family
ID=32038536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200380101276 Pending CN1703193A (en) | 2002-10-11 | 2003-10-08 | Fragrance composition including an ionic liquid, its preparation and use |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1703193A (en) |
| DE (1) | DE10337579A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103929962A (en) * | 2011-08-16 | 2014-07-16 | 巴斯夫欧洲公司 | Composition comprising active ingredient, oil and ionic liquid |
| CN104853738A (en) * | 2012-12-20 | 2015-08-19 | 高露洁-棕榄公司 | Oral care composition containing ionic liquids |
| CN105007885A (en) * | 2013-03-13 | 2015-10-28 | 荷兰联合利华有限公司 | Prolonged delivery of certain fragrance components from personal care compositions |
| CN107072913A (en) * | 2014-09-25 | 2017-08-18 | 宝洁公司 | Perfume composition comprising ionic liquid |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005032798A1 (en) * | 2005-07-14 | 2007-01-25 | Henkel Kgaa | Agent for dyeing and / or lightening keratinic fibers with novel active ingredients |
| US9278134B2 (en) | 2008-12-29 | 2016-03-08 | The Board Of Trustees Of The University Of Alabama | Dual functioning ionic liquids and salts thereof |
| MX352873B (en) | 2013-03-13 | 2017-12-13 | Unilever Nv | Photoprotective compositions with tricyclodecane amides. |
| JP6364032B2 (en) | 2013-03-13 | 2018-07-25 | ユニリーバー・ナームローゼ・ベンノートシヤープ | Cosmetic composition comprising tricyclodecanamide |
-
2003
- 2003-08-16 DE DE10337579A patent/DE10337579A1/en not_active Withdrawn
- 2003-10-08 CN CN 200380101276 patent/CN1703193A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103929962A (en) * | 2011-08-16 | 2014-07-16 | 巴斯夫欧洲公司 | Composition comprising active ingredient, oil and ionic liquid |
| CN103929962B (en) * | 2011-08-16 | 2016-12-07 | 巴斯夫欧洲公司 | Comprise the compositions of active component, oil and ionic liquid |
| CN104853738A (en) * | 2012-12-20 | 2015-08-19 | 高露洁-棕榄公司 | Oral care composition containing ionic liquids |
| CN105007885A (en) * | 2013-03-13 | 2015-10-28 | 荷兰联合利华有限公司 | Prolonged delivery of certain fragrance components from personal care compositions |
| CN105007885B (en) * | 2013-03-13 | 2018-06-26 | 荷兰联合利华有限公司 | The extension delivering of certain aromatised fractions in personal care composition |
| CN107072913A (en) * | 2014-09-25 | 2017-08-18 | 宝洁公司 | Perfume composition comprising ionic liquid |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10337579A1 (en) | 2004-04-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20060166856A1 (en) | Fragrance composition comprising at least one ionic liquid, method for production and use thereof | |
| US20030083513A1 (en) | Functional alcohol releasing substance | |
| WO2018202311A1 (en) | Composition for odour improvement | |
| CN1703193A (en) | Fragrance composition including an ionic liquid, its preparation and use | |
| CN1784210A (en) | Sprayable perfume with an improved tenacity | |
| EP2119694B1 (en) | Optically Active Ester Compounds and their use in Perfume Compositions | |
| ES2375086T3 (en) | CICLOALQUILIDENO- (REPLACED ORTO PHENYL) -ACETONITRILS AND ITS USE AS ODORANTS. | |
| US7763742B2 (en) | Hexahydro-4H-indeno acetonide fragrance compound | |
| US11504310B2 (en) | Aqueous microemulsion | |
| EP3233821A1 (en) | Orthoformic acid esters as pro-fragrances | |
| EP3233781B1 (en) | Photolabile fragrance precursor compound | |
| EP1496055B1 (en) | Acetonide fragrance compound | |
| EP3692126B1 (en) | Pro-fragrances and method of preparation thereof | |
| WO2017045891A1 (en) | Diazirines as photocages which release molecules containing double bonds | |
| EP2904078B1 (en) | Flavor and fragrance formulation (vi) | |
| US9944585B2 (en) | Flavor and fragrance formulation (V) | |
| US6906013B1 (en) | Cyclohexanbutanol derivative and fragrance use thereof | |
| JP2010090317A (en) | Fragrance, and composition containing the same | |
| JPH064870B2 (en) | Method of improving retention of aroma components | |
| WO2019101444A1 (en) | Hydrolytically labile heterocycles of odoriferous ketones or odoriferous aldehydes | |
| WO2019114969A1 (en) | Aromatic substance mixtures containing 8,8-dimethyl-6,10-dioxaspiro[4,5]decane | |
| DE102017124612A1 (en) | Hydrolysis-labile dienol silyl ethers of fragrance ketones or aldehydes | |
| DE102017124611A1 (en) | Thermolabile fragrance storage substances of fragrance ketones | |
| JP2015526418A6 (en) | Antimicrobial agent | |
| JP2015526418A (en) | Antimicrobial agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |