NL8302893A - PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW. - Google Patents
PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW. Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
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Description
SO 31952 fr* * 2 * * r Parfumcomposities en geparfumeerde produkten die ten minste één of meer esters van 2-ethyl-2-methyl-butaanzuur als parfumgrondstof bevatten.SO 31952 fr * * 2 * * r Perfume compositions and perfumed products containing at least one or more esters of 2-ethyl-2-methyl-butanoic acid as perfume raw material.
De uitvinding heeft betrekking op parf umcomposities die ten minste één of meer esters van 2-ethyl-2-methyl-butaanzuur als parfumgrondstof bevatten en op met deze verbindingen respectievelijk deze verbindingen bevattende parfumcomposities geparfumeerde produkten.The invention relates to perfume compositions containing at least one or more esters of 2-ethyl-2-methyl-butanoic acid as perfume raw material and to perfume compositions perfumed with these compounds or these compounds respectively.
5 Er is een voortdurende belangstelling voor de bereiding en toe passing van synthetische reukstoffen omdat deze, in tegenstelling tot natuurprodukten, altijd in een aan de vraag aangepaste hoeveelheid en gelijkmatige kwaliteit kunnen worden bereid.There is a continuing interest in the preparation and use of synthetic fragrances because, unlike natural products, they can always be prepared in demand-matched quantity and uniform quality.
Gevonden werd nu dat esters van 2-ethyl-2-me thyl-butaanzuur met 10 de algemene, formule % C% .Esters of 2-ethyl-2-methyl-butanoic acid with the general formula% C% were now found.
c' / \ cJl coor waarin R een alkyl-, alkenyl-, alkoxyalkyl-, cycloalkyl-, alkylcyclo-alkyl-, cycloalkylalkyl- of aralkylgroep met maximaal 8 koolstofatomen voorstelt, waardevolle reukstoffen zijn. Zij zijn in staat om aan parfumcomposities en produkten velerlei gewenste geurnoten te verlenen, 15 met name geurnoten van het groene, vruchtige, muntige, houtige,en bloemige type. Speciaal de ethylester onderscheidt zich door een natuurlijk geurkarakter. Deze ethylester is beschreven in het Britse octrooischrift 1.004.286 en door J.R. Roland, J.D.C. Wilson en W.E. Hanford in J.Am. Chem. Soc. 72, 2122-24 (1950). In beide publi-20 caties zijn echter geen aanwijzingen te vinden voor de bruikbaarheid van deze verbinding als parfumgrondstof. Met betrekking tot de bovengrens van 8 koolstofatomen wordt volledigheidshalve vermeld, dat de vluchtigheid en derhalve de geursterkte van esters van 2-ethyl-2-methyl-butaanzuur,waarin R meer dan 8 koolstofatomen bevat, onvoldoende 25 wordt beoordeeld.C 1 / C 11 wherein R represents an alkyl, alkenyl, alkoxyalkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl or aralkyl group of up to 8 carbon atoms are valuable fragrances. They are capable of imparting to perfume compositions and products a variety of desirable notes, especially notes of the green, fruity, minty, woody, and floral type. The ethyl ester in particular is distinguished by a natural scent character. This ethyl ester is described in British Patent 1,004,286 and by J.R. Roland, J.D.C. Wilson and W.E. Hanford in J.Am. Chem. Soc. 72, 2122-24 (1950). However, there is no evidence in both publications of the utility of this compound as a perfume raw material. With regard to the upper limit of 8 carbon atoms, it is stated for the sake of completeness that the volatility and, therefore, the odor strength of esters of 2-ethyl-2-methyl-butanoic acid, in which R contains more than 8 carbon atoms, is insufficiently assessed.
De esters volgens de uitvinding worden bereid volgens alge neen bekende veresteringsmethoden, bijvoorbeeld door reactie van de overeenkomstige alcohol met 2-ethyl-2-me thyl-butaanzuur of een gebruikelijke derivaat daarvan zoals het zuurchloride.The esters according to the invention are prepared according to known esterification methods, for example by reacting the corresponding alcohol with 2-ethyl-2-methyl-butanoic acid or a conventional derivative thereof such as the acid chloride.
3302893 r * i 7 23302893 r * i 7 2
De esters volgens de uitvinding kunnen met succes worden toegepast in parfumcomposities, of als zodanig worden gebruikt als geur-verlenend middel in allerlei produkten. Met de uitdrukking "parfumcom-positie" wordt hier bedoeld een mengsel van reukstoffen en eventueel 5 hulpstoffen, desgewenst opgelost in een geschikt oplosmiddel of gemengd met een poedervormig substraat, dat wordt gebruikt om een gewenste geur te verlenen aan de huid en/of allerlei produkten. Voorbeelden van zulke produkten zijn: zepen, detergenten, luchtverfrissers, ruim-tesprays, pommanders, kaarsen, cosmetica, zoals crèmes, zalven, 10 toiletwaters, pre- en aftershave lotions, talkpoeders, haarverzor-gingsmiddelen, lichaamsdeodorantia en antitranspiratieraiddelen.The esters according to the invention can be used successfully in perfume compositions, or as such can be used as a fragrance-imparting agent in a variety of products. By the term "perfume composition" is meant herein a mixture of fragrances and optional auxiliaries, optionally dissolved in a suitable solvent or mixed with a powdery substrate, which is used to impart a desired fragrance to the skin and / or all kinds of products . Examples of such products are: soaps, detergents, air fresheners, room sprays, pommanders, candles, cosmetics, such as creams, ointments, toilet waters, pre- and aftershave lotions, talcum powders, hair care products, body deodorants and anti-perspirants.
Reukstoffen en reukstofmengsels^ welke in combinatie met de verbindingen volgens de uitvinding kunnen worden gebruikt voor de bereiding van parfumcomposities zijn bijvoorbeeld: natuurlijke produkten 15 zoals etherische oliën, absolues, resinoïden, harsen, concretes enz., maar ook synthetische reukstoffen zoals koolwaterstoffen, alcoholen, aldehyden, ketonen, ethers, zuren, esters, acetalen, ketalen, nitrilen enz., waaronder verzadigde en overzadigde verbindingen, alifatische, carbocyclische en heterocyclische verbindingen. Voorbeelden van reuk-20 stoffen die kunnen worden gebruikt in combinatie met de verbindingen volgens de uitvinding zijn: geraniol, geranylacetaat, linalool, lina-lylacetaat, tetrahydrolinalool, citronellol, citronellylacetaat, di-hydromyrcenol, dihydromyrcenylacetaat, tetrahydromyrcenol, terpineol, 83 0 2 8 9 3 3 * « , terpinylacetaat, nopol, nopyXacetaat, 2-fenylethanol, 2-fenylethyX- acetaat, benzylalcohol, benzylacetaat, benzylsalicylaat, styrallyl-acetaat, benzylbenzoaat, amylsalicylaat, dimethylbenzylcarbinol, tri-chloormethylfenylcarbinylacetaat, p-tert.butyl-cyclohexylacetaat, iso-5 nonylacetaat, vetiverylacetaat, vetiverol, aXfa-hexyXkaneeXaldehyde, 2-methyl-3-(p-tert.butylfenyl)-propanal, 2-methyl~3-(p-isopropylfe-nyl)-propanal, 3-(p-tert.butylfenyl)-propanal, tricyclodecenylacetaat, tricyclodecenyipropionaat, 4-(4-hydroxy-4-methylpentyL) -3-cyclohexeen-carbaldebyde, 4-(4-methyl-3-pentenyl)-3-cyclohexeencarbaldehyde, 10 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pen.tylcyclo-peataan, 2-n-heptylcyclopentanon, 3 -methyl-2-pentyl-2-cyclop entenon, a-decanal, n-dodecanaX, 9-decenol-l> fenoxyethyl-isobutyraat, fenyl-aceetaldehyde-dimethylacetaal, fenylaceetaldehyde-diethylacetaal, geranylnitril, citronellyinitril, cedryXacetaat, 3-isokamfylcyclo-15 hexanoX, cedrylmethylether, isolongifolanon, aubepinenitril, aubepine, heliotropine, coumarine, eugenol, vanilliert, difenyloxyde, hydroxy-citronellal, joaonen, methyljononen, isomethyljononen, iroaen, cis-3-hexenol en esters daarvan, indan-muskusreukstoffen, tetralienmuskus-reukstoffen, is o chromanmus kus reuks to f fen, macrocyclische ketonen, 20 macroXactonmuskusreukstoffen, ethyXeenbrassyiaat, aromatische nitro-muskusreukstoffen.Fragrances and perfume mixtures which can be used in combination with the compounds according to the invention for the preparation of perfume compositions are for example: natural products such as essential oils, absolute, resinoids, resins, concretes, etc., but also synthetic fragrances such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and supersaturated, aliphatic, carbocyclic, and heterocyclic compounds. Examples of fragrances that can be used in combination with the compounds of the invention are: geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalole, citronellol, citronelly acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpine 8 9 3 3 * «, terpinyl acetate, nopol, nopylaacetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amylsalicylate, trichloroethyl acetyl, trichlorethylethyl iso-5-nonylacetate, vetiveryl acetate, vetiverol, aXfa-hexyXkaneeXaldehyde, 2-methyl-3- (p-tert-butylphenyl) -propanal, 2-methyl-3- (p-isopropylphenyl) -propanal, 3- (p- tert-butylphenyl) -propanal, tricyclodecenyl acetate, tricyclodecenyipropionate, 4- (4-hydroxy-4-methylpentyL) -3-cyclohexene-carbaldebyde, 4- (4-methyl-3-pentenyl) -3-cyclohexene-carbaldehyde, 10 4- 3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pin .tyl cyclo-peatane, 2-n-heptyl cyclopentanone, 3-methyl-2-pentyl-2-cyclop entenone, a-decanal, n-dodecanaX, 9-decenol-1-phenoxyethyl isobutyrate, phenyl acetaldehyde dimethyl acetaldehyde acetaldehyde diethyl acetal, geranyl nitrile, citronellyinitrile, cedryxacetate, 3-isokamphylcyclo-15 hexanoX, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropin, coumarin, eugenol, vanilliert, diphenyloxethyl, hydroxy-joonone and esters thereof, musk fragrances, tetral musk fragrances, are chromanmus kiss odors, macrocyclic ketones, macroxacton musk fragrances, ethylene brassyl aromatic, nitro musk fragrances.
Hulpstoffen en oplosmiddelen die gebruikt kunnen worden in parfum-composifcies, welke één of meer verbindingen volgens de uitvinding bevatten, zijn bijvoorbeeld: ethanol, isopropanol, diethyleenglycolmonoethylether, 25 diethylftalaafc enzovoorts.Excipients and solvents which can be used in perfume compositions containing one or more compounds of the invention are, for example: ethanol, isopropanol, diethylene glycol monoethyl ether, diethylphthalafafc and so on.
83 5 2 Π 53 4 w «r83 5 2 Π 53 4 w
De hoeveelheden waarin de verbindingen- volgens de uitvinding kunnen worden toegepast in parfumcomposities of te parfumeren produkten kunnen binnen ruime grenzen variëren en hangen onder meer af van de aard van het produkt waarin de reukstof wordt toegepast, van de aard 5 en de hoeveelheid van de overige componenten in de parfumcompositie en van het geureffect dat wordt beoogd. Daarom is het slechts mogelijk zeer globale grenzen aan te geven, waarmee echter voor de deskundige voldoende informatie wordt verschaft om de verbindingen volgens de uitvinding zelfstandig te kunnen toepassen. In de meeste gevallen zal 10 een hoeveelheid van slechts 0,1 gew.% in een parfumcompositie reeds voldoende zijn om een duidelijk waarneembaar geureffect te verkrijgen. Anderzijds is het voor het bereiken van speciale geureffecten mogelijk om hoeveelheden van 20 gew.% of zelfs meer in een compositie toe te passen. In met behulp van parfumcomposities geparfumeerde produkten 15 liggen deze concentraties evenredig lager, afhankelijk van de toege-pasfce hoeveelheid parfumcompositie in het produkt.The amounts in which the compounds according to the invention can be used in perfume compositions or products to be perfumed can vary within wide limits and depend, inter alia, on the nature of the product in which the fragrance is used, on the nature and the amount of the other components in the perfume composition and of the fragrance effect that is intended. Therefore, it is only possible to indicate very global limits, however, with which the person skilled in the art is provided with sufficient information to be able to use the compounds according to the invention independently. In most cases, an amount of only 0.1% by weight in a perfume composition will already be sufficient to obtain a clearly perceptible odor effect. On the other hand, to achieve special fragrance effects, it is possible to use amounts of 20% by weight or even more in a composition. In products perfumed with the aid of perfume compositions, these concentrations are proportionately lower, depending on the amount of perfume composition used in the product.
De volgende voorbeelden dienen uitsluitend ter illustratie van de bereiding en toepassing van de verbindingen volgens de uitvinding. De uitvinding is daartoe evenwel niet beperkt.The following examples serve only to illustrate the preparation and use of the compounds of the invention. However, the invention is not limited thereto.
2° Voorbeeld I2 ° Example I
Bereiding van ethyl-2~ethyl-2-raethyl-butyraat.Preparation of ethyl 2-ethyl-2-raethyl-butyrate.
Aan een mengsel van 260 g (2 mol) 2-ethyl-2-methyl-butaanzuur en 386 g (8 mol) ethanol wordt onder goed roeren in 15 minuten 260 g geconcentreerd zwavelzuur toegevoegd. Daarbij stijgt de temperatuur tot ca. 25 60°C. Het mengsel wordt vervolgens al roerende nog 3 uur verhit onder reflux. Nadat het mengsel is afgekoeld tot kamertemperatuur, worden de lagen gescheiden.To a mixture of 260 g (2 mol) of 2-ethyl-2-methyl-butanoic acid and 386 g (8 mol) of ethanol, 260 g of concentrated sulfuric acid are added over 15 minutes with good stirring. The temperature thereby rises to approx. 25 60 ° C. The mixture is then heated under reflux for a further 3 hours while stirring. After the mixture has cooled to room temperature, the layers are separated.
87 Λ .“i ** T87 Λ. “I ** T
o u o y o k 5o u o y o k 5
De onderlaag wordt verdund met 200 ml water én vervolgens geëxtraheerd met cyclohexaan. De cyclohexaanlaag wordt verenigd met de oorspronkelijke bovenlaag en neutraal gewassen met soda-oplossing. De cyclo-hexaanoplossing wordt vervolgens ingedampt en het residu gedestilleerd 5 onder verminderde druk. Verkregen wordt 258 g van de gewenste ethyl-ester, kpt-: 65°C/0,3 kPa; n20/D = 1,4110; NïlR (100 HHz, 6 in ppra t.o.v. TMS, oplosmiddel: CC14): 0,81 (6H,t,J = 7Hz); 1,06 (3H,s); 1,24 (3H,t,J = 7Hz); 1,0-1,9 (4H,m); 4,08 (2H,q,J = 7Hz).The bottom layer is diluted with 200 ml of water and then extracted with cyclohexane. The cyclohexane layer is combined with the original top layer and washed neutral with soda solution. The cyclohexane solution is then evaporated and the residue distilled under reduced pressure. 258 g of the desired ethyl ester are obtained, bpt: 65 ° C / 0.3 kPa; n20 / D = 1.4110; NiR (100 HHz, 6 in ppra to TMS, solvent: CC14): 0.81 (6H, t, J = 7Hz); 1.06 (3H, s); 1.24 (3H, t, J = 7Hz); 1.0-1.9 (4H, m); 4.08 (2H, q, J = 7Hz).
De verbinding heeft een aangenaam vruchtige en houtige geur met as-10 pecten die herinneren aan tagetesolie.The compound has a pleasantly fruity and woody fragrance with as-10 pects reminiscent of tagetes oil.
Voorbeeld IIExample II
Bereiding van 2' -ethylhexyl- (2 -ethy 1 -2-methy 1) -butyraa t.Preparation of 2 '-ethylhexyl- (2-ethyl-1 -2-methyl-1) -butyrate.
Een mengsel van 15,5 g (0,12 mol) 2-ethylhexanol, 13 g (0,1 nol) 2-ethyl-2-methyl-butaanzuur, 100 mg p-tolueensulfonzuur en 150 ml 15 tolueen wordt verhit tot reflux waarbij het gevormde water azeo-tropisch wordt afgedestilleerd. Nadat het mengsel is afgekoeld tot kamertemperatuur, wordt het neutraal gewassen met soda-oplossing. De tolueenoplossing wordt vervolgens ingedarapt en het residu gedestilleerd onder verminderde druk. Verkregen wordt 14,5 g van de gewenste 20 ester, kpt.: 95°C/0,3 kPa; n24/D = 1,4320; NMR: 0,81 (6H,t,J = 7Hz); 1,05 (3H,s); 0,6-1,9 (19H,m); 3,90 (2H,d,J = 6Hz).A mixture of 15.5 g (0.12 mol) 2-ethylhexanol, 13 g (0.1 nol) 2-ethyl-2-methyl-butanoic acid, 100 mg p-toluenesulfonic acid and 150 ml toluene is heated to reflux the water formed is distilled azeo-tropically. After the mixture has cooled to room temperature, it is neutral washed with soda solution. The toluene solution is then evaporated and the residue distilled under reduced pressure. 14.5 g of the desired ester are obtained, b.p .: 95 ° C / 0.3 kPa; n24 / D = 1.4320; NMR: 0.81 (6H, t, J = 7Hz); 1.05 (3H, s); 0.6-1.9 (19H, m); 3.90 (2H, d, J = 6Hz).
De verbinding heeft een aangenaam muntige en enigszins vruchtige geur.The compound has a pleasantly minty and slightly fruity fragrance.
rs v -rs v -
- v v _ .. o- -J- v v _ .. o- -J
66
r· Voorbeeld IIIr · Example III
De onderstaande esters werden bereid zoals beschreven is in voorbeeld II:The esters below were prepared as described in Example II:
Allyl-2-ethyl-2-methyl-butyraat: 5 kpt.: 95°C/0,3 kPa; NMR: 0,81 (6H,t,J = 7Hz), 1,08 (3H,s); 1,0-1,9 C4H,m); 4,49 (2H,d met fijnstructuur, J = 7Hz); 5,0-5,4 (2H,m); 5,6-6,1 (lH,m).Allyl-2-ethyl-2-methyl-butyrate: 5pt .: 95 ° C / 0.3 kPa; NMR: 0.81 (6H, t, J = 7Hz), 1.08 (3H, s); 1.0-1.9 C4H, m); 4.49 (2H, d with fine structure, J = 7Hz); 5.0-5.4 (2H, m); 5.6-6.1 (1H, m).
Kruidig groene en bloemige geur, enigszins herinnerend aan tagetesolie. Isobutyl-2-ethyl-2-methyl-butyraat: 10 kpt.: 90°C/0,3 KPa; n20/D = 1,4155; NMR:0,8I (6H,t,J = 7Jz); 0,94 (6H,d,J = 7Hz); 1,06 (3H,s); 1,0-2,2 (5H,m); 3,78 (2H,d,J = 6Hz). Houtige en muntige geur met bloemige aspecten.Spicy green and floral fragrance, somewhat reminiscent of tagetes oil. Isobutyl-2-ethyl-2-methyl-butyrate: 10 kpt .: 90 ° C / 0.3 KPa; n20 / D = 1.4155; NMR: 0.8I (6H, t, J = 7Jz); 0.94 (6H, d, J = 7Hz); 1.06 (3H, s); 1.0-2.2 (5H, m); 3.78 (2H, d, J = 6Hz). Woody and minty fragrance with floral aspects.
Cyclohexyl-2-ethyl-2-methyl-butyraat: kpt.: 90°C/0,3 kPa; n20/D = 1,4462; NMR: 0,80 (6H,t,.T = 7Hz); 1,04 15 (3H,s); 1,0-2,0 (14H,m); 4,65 (lH,m) .Cyclohexyl-2-ethyl-2-methyl-butyrate: bp: 90 ° C / 0.3 kPa; n20 / D = 1.4462; NMR: 0.80 (6H, t, T = 7Hz); 1.04 (3H, s); 1.0-2.0 (14H, m); 4.65 (1H, m).
Vruchtige geur.Fruity fragrance.
21-methoxyethyl-(2-ethyl-2-methyl)-butyraat: kpt.: 75°C/0,3 kPa; JMR: 0,81 (6H,t,7Hz); 1,06 (3H,s); 1,0-1,9 (4H,m); 3,30 (3H,s); 3,46 (2H, t,J = 5Hz); 4,12 (2H,t,J = 5Hz).21-methoxyethyl- (2-ethyl-2-methyl) -butyrate: bp: 75 ° C / 0.3 kPa; JMR: 0.81 (6H, t, 7Hz); 1.06 (3H, s); 1.0-1.9 (4H, m); 3.30 (3H, s); 3.46 (2H, t, J = 5Hz); 4.12 (2H, t, J = 5Hz).
20 Groene en enigszins houtige geur.20 Green and slightly woody fragrance.
Benzyl-2-ethyl-2-methyl-butyraat: kpt.: 118°C/0,3 kPa; n20/D = 1,4890; NMP: 0,77 (6H,t,J = 7Jz); 1,07 (3H,s); 1,0-1,9 (4H,m); 5,00 (2H,s); 7,0-7,3 (5H, breed s).Benzyl-2-ethyl-2-methyl-butyrate: bp: 118 ° C / 0.3 kPa; n20 / D = 1.4890; NMP: 0.77 (6H, t, J = 7Jz); 1.07 (3H, s); 1.0-1.9 (4H, m); 5.00 (2H, s); 7.0-7.3 (5H, broad s).
Groene en enigszins bloemige geur.Green and slightly floral fragrance.
83 0 2 0 9 3 * 7 2' -fenyleth.yl-(2-eth.yl-2-raeth.yl)-fautyraat: kpt.: 125°C/0,3 kPa; n20/D = 1,4830; NMR:0,73 (6H,t,J = 7Hz); 1,01 (3H,s); 1,0-1,9 (4H,m); 2,86 (2H,t,J = 7Hz); 4,20 (2H,t,J = 7Kz); 6,9-7,3 (5H, breed s).83 0 2 0 9 3 * 7 2'-phenylethyl- (2-eth.yl-2-raeth.yl) -fautyrate: bp: 125 ° C / 0.3 kPa; n20 / D = 1.4830; NMR: 0.73 (6H, t, J = 7Hz); 1.01 (3H, s); 1.0-1.9 (4H, m); 2.86 (2H, t, J = 7Hz); 4.20 (2H, t, J = 7Kz); 6.9-7.3 (5H, broad s).
5 Bloemige en enigszins vruchtige geur.5 Floral and slightly fruity fragrance.
83 0 2 3 33 8 -2 \ %83 0 2 3 33 8 -2%
Voorbeeld IVExample IV
Een parfumcompositie van het dennen-type, zeer geschikt voor shampoos en douche- en badschuimpreparaten, werd bereid volgens onderstaand recept:A pine-type perfume composition, very suitable for shampoos and shower and bubble bath preparations, was prepared according to the following recipe:
VV
5 345 gewichtsdelen bornylacetaat 100 " 2-butyl-4,4,6-trimethyl-l,3-dioxaan 50 " Siberische dennenaaldenolie 30 " 5-acetyl-3-isopropyl-l,1,2,6-tetra- methyl-indan 1Ö 30 ” benzylacetaat 30 ” sinaasappelolie 30 " linalylacetaat 20 " olibanum-resinoide 20 " tridecanal 15 15 " 4-tert.butylcyclohexylacetaat j 10 " coumarine 10 " terpineol 10 " terpinylacetaat 10 " lavandinolie 20 10 " n-decanal 7 ” Citrovertal NB 104* 5 " dodecanal 5 " styralylacetaat 5 " 3-isokamfylcyclohexanol 25 3 " a-jonon 2 " isoeugenol 30 " ethyl-2-ethyl-2-methyl-butyraat 218 " dipropyleenglycol 1000 gewichtsdelen 8302893 > -Tr . ο.5 345 parts by weight bornyl acetate 100 "2-butyl-4,4,6-trimethyl-1,3-dioxane 50" Siberian pine needle oil 30 "5-acetyl-3-isopropyl-1,2,6,6-tetramethyl-indan 1Ö 30 "benzyl acetate 30" orange oil 30 "linalyl acetate 20" olibanum-resinoid 20 "tridecanal 15 15" 4-tert-butylcyclohexyl acetate j 10 "coumarin 10" terpineol 10 "terpinyl acetate 10" lavandin oil 20 10 "n-decanal 7 104" Citrovert * 5 "dodecanal 5" styralyl acetate 5 "3-isokamphylcyclohexanol 25 3" α-ionone 2 "isoeugenol 30" ethyl-2-ethyl-2-methyl-butyrate 218 "dipropylene glycol 1000 parts by weight 8302893-Tr. Ο.
* 9* 9
' Voorbeeld VExample V
Een parfumcompositie van het type bloemen-fantasie werd bereid volgens onderstaand recept: 350 gewichtsdelen Muguet base* 5 200 " Lilas base* 175 '* Jasmin base* 75 " Hyacinth base* 70 " bois-de-rose-olie 70 11 dihydromyrcenol 1Ó 50 " ylang-ylang-olie 40 " tricyclodecenylacetaat 40 ” 2-(heptyl-3)-dioxolaan 30 " litsea-cubeba-olie 20 " dimethyl-benzyl-carbinylacetaat 15 10 " eugenol 10 " 5-acetyl-3-isopropyl-l,l,2.6-tetra- methylindan 3 " 2,4-dimethyl-cycloh.exeen-3- carbaldehyde 20 2 " isoeugenol 50 " ethyl-2-ethyl-2-methyl-butyraat 1200 gewichtsdelenA floral fantasy perfume composition was prepared according to the following recipe: 350 parts by weight of Muguet base * 5 200 "Lilas base * 175" * Jasmin base * 75 "Hyacinth base * 70" bois de rose oil 70 11 dihydromyrcenol 100 "ylang-ylang oil 40" tricyclodecenyl acetate 40 "2- (heptyl-3) -dioxolane 30" litsea cubeba oil 20 "dimethyl benzyl carbinyl acetate 15 10" eugenol 10 "5-acetyl-3-isopropyl-1, 1,2,6-tetramethylindan 3 "2,4-dimethyl-cyclohexene-3-carbaldehyde 20 2" isoeugenol 50 "ethyl-2-ethyl-2-methyl-butyrate 1200 parts by weight
De aldus vervaardigde parfumcompositie kan met succes worden toe gepast in luchtverffeissingspreparaten vervaardigd volgens het Britse octrooischrift 25 1.544.221.The perfume composition thus prepared can be successfully used in air-dyeing compositions made according to British Patent Specification 1,544,221.
K Parfumbasen, in de handel gebracht door Naarden International N.V.K Perfume bases, marketed by Naarden International N.V.
33δ.ζ C 9 333δ.ζ C 9 3
Claims (5)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL8302893A NL8302893A (en) | 1983-08-17 | 1983-08-17 | PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW. |
EP84201183A EP0134613A1 (en) | 1983-08-17 | 1984-08-14 | Perfume compositions and perfumed products which contain at least one or more esters of 2-ethyl-2-methyl-butanoic acid as the perfume base |
JP17008484A JPS6067445A (en) | 1983-08-17 | 1984-08-16 | Perfume composition and perfumed product |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL8302893 | 1983-08-17 | ||
NL8302893A NL8302893A (en) | 1983-08-17 | 1983-08-17 | PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW. |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8302893A true NL8302893A (en) | 1985-03-18 |
Family
ID=19842279
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8302893A NL8302893A (en) | 1983-08-17 | 1983-08-17 | PERFUME COMPOSITIONS AND PERFUMED PRODUCTS CONTAINING AT LEAST ONE OR MORE ESTERS OF 2-ETHYL-2-METHYL-BUTANIC ACID AS PERFUME RAW. |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0134613A1 (en) |
JP (1) | JPS6067445A (en) |
NL (1) | NL8302893A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5080776B2 (en) * | 2006-10-06 | 2012-11-21 | 花王株式会社 | Ester compound |
EP3597626A1 (en) * | 2018-07-19 | 2020-01-22 | Basf Se | Alpha,alpha-disubstituted carboxylic acid esters for use as aroma chemicals |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2626142A1 (en) * | 1976-06-11 | 1977-12-22 | Henkel Kgaa | USE OF ALIPHATIC 2-METHYL-2-ALKYL ALKANOIC ACID ESTERS AS FRAGRANCE SUBSTANCES AND FRAGRANCE COMPOSITIONS CONTAINING THEM |
-
1983
- 1983-08-17 NL NL8302893A patent/NL8302893A/en not_active Application Discontinuation
-
1984
- 1984-08-14 EP EP84201183A patent/EP0134613A1/en not_active Withdrawn
- 1984-08-16 JP JP17008484A patent/JPS6067445A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS6067445A (en) | 1985-04-17 |
EP0134613A1 (en) | 1985-03-20 |
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