WO1999043639A1 - Systemes de diffusion de substances brutes de fragrances a base d'alcools tertiaires - Google Patents

Systemes de diffusion de substances brutes de fragrances a base d'alcools tertiaires Download PDF

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Publication number
WO1999043639A1
WO1999043639A1 PCT/US1999/002733 US9902733W WO9943639A1 WO 1999043639 A1 WO1999043639 A1 WO 1999043639A1 US 9902733 W US9902733 W US 9902733W WO 9943639 A1 WO9943639 A1 WO 9943639A1
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Prior art keywords
alkenyl
branched
alkyl
pro
fragrance
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PCT/US1999/002733
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English (en)
Inventor
Greg Scot Miracle
Kenneth Nathan Price
Lon Montgomery Gray
Scott William Waite
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The Procter & Gamble Company
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Priority to CA002321846A priority Critical patent/CA2321846A1/fr
Priority to BR9908220-9A priority patent/BR9908220A/pt
Priority to JP2000533398A priority patent/JP2002504532A/ja
Priority to EP99905882A priority patent/EP1056702A1/fr
Publication of WO1999043639A1 publication Critical patent/WO1999043639A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/32—Compounds having groups or groups

Definitions

  • the present invention relates to pro-accords which are capable of releasing tertiary alcohol fragrance raw materials inter alia linalool, tertahydrolinalool, ethyllinalool, and dihydromyrcenol.
  • the present invention also relates to fragrance delivery systems which comprise said pro-accords thereby providing a means for delivering tertiary alcohol fragrance raw materials to a situs, preferably human skin.
  • the present invention further relates to fine fragrances and perfumes which comprise said tertiary alcohol releasing fragrance delivery systems.
  • the fragrance delivery systems described herein also provide for fragrance longevity.
  • fragrance raw materials Many modern fragrances are no longer derived from natural sources but are synthesized by modern chemical methods as highly pure fragrance raw materials (FRM). These FRM's are currently formulated to produce fine perfumes, colognes, eau de toilettes, after-shave lotions, and other personal fragrance compositions. Those skilled in the art of preparing these fragrance-containing compositions have categorized fragrances into three types based on their relative volatility; top, middle, and base notes.
  • a drawback of typical fine fragrances and perfumes is that the original scent, which is a balance of fragrance raw materials, begins to change once the perfume or fragrance has been applied to human skin. This loss of fragrance balance is in part due to differential evaporation of the more volatile top notes, and to absorption of other ingredients into the skin surface. Users of perfumes and fine fragrances have attempted to rectify this problem in 2
  • One method is to initially "load up” on the amount of perfume and rely upon the - natural evaporation rate to diminish the fragrance to a suitable level several hours later when the desired effect is needed.
  • Another method commonly employed is to continually renew the fragrance by reapplying small amounts of the perfume to the skin at short time intervals.
  • Neither of these solutions is adequate to overcome the diminishing level of top and middle notes over time.
  • base notes which are present over a protracted period by virtue of their low volatility, begin to accumulate with each "re-freshing" of perfume and after a time the base notes begin to overwhelm the other fragrance notes and destroy the original fragrance balance.
  • some fragrance raw materials can be delivered to human skin via pro-perfumes.
  • pro-perfume compounds include acid labile acetals, ketals, and orthoesters which breakdown upon contact with the acidic pH on the human skin surface resulting in the release of fragrance raw materials.
  • acetals release aldehydes
  • ketals release ketones
  • orthoesters release alcohols.
  • the formulator has been limited by the fact that some pro-perfumes, although acid labile, have a fragrance release half-life (hydrolysis rate) which is beyond the time which is of utility for use in fine fragrances or perfume compositions.
  • the prior art does not disclose pro-perfumes which suitably release tertiary alcohol fragrance raw materials.
  • certain orthoester pro-accords are capable of delivering one or more tertiary alcohol fragrance raw materials at a rate which provides a useful means for delivering these desirable fragrance raw materials to human skin.
  • the pro-accords described herein are modifiable to deliver tertiary alcohols at rates which are preferred by the formulator.
  • the present invention meets the aforementioned needs in that it has been surprisingly discovered that certain orthoesters comprising at least one tertiary alcohol fragrance raw material can be prepared which release said tertiary alcohol at a rate which can be adjusted to meet the specific needs of the formulator.
  • the protracted release of fragrance raw materials provides the formulator with a means of extending the original perfume raw material blend, or initial fragrance note.
  • the formulator can now controllably release tertiary alcohol fragrance raw materials. This controlled release is a means for providing longevity of tertiary alcohol fragrances on human skin.
  • a first aspect of the present invention relates to pro-accords having the formula:
  • each -OR 1 , -OR 2 , and -OR 3 moiety is an alkoxy unit derived from an alcohol such that each R 1 , R 2 , and R 3 is independently substituted or unsubstituted C ⁇ -C 20 linear alkyl, C 3 - C 2 o branched alkyl, C 3 -C 20 cyclic alkyl, C -C 2 o branched cyclic alkyl, C 3 -C 20 linear alkenyl, C 4 -C 2 o branched alkenyl, C 3 -C 2 o cyclic alkenyl, C -C 2 o branched cyclic alkenyl, C 6 -C 2 o aryl, C 6 -C 2 o alkylenearyl, C6-C20 alkyleneoxyalkyl, C 6 -C 2 o alkyleneoxyaryl, and mixtures thereof; or any two R 1 , R 2 , or R 3 can be taken together to
  • the present invention further relates to a fragrance delivery system which comprises at least one pro-accord as described herein capable of suitably releasing a tertiary alcohol fragrance raw material together with one or more pro-accords inter alia orthoesters, ketals, acetals, orthocarbonates, preferably having a fragrance release half-life of greater than or equal to 0.1 hours at pH 5.3 and less than or equal to 12 hours at pH 2.5 when said fragrance release half-life is measured in a NaH 2 P0 buffer at said pH.
  • a fragrance delivery system which comprises at least one pro-accord as described herein capable of suitably releasing a tertiary alcohol fragrance raw material together with one or more pro-accords inter alia orthoesters, ketals, acetals, orthocarbonates, preferably having a fragrance release half-life of greater than or equal to 0.1 hours at pH 5.3 and less than or equal to 12 hours at pH 2.5 when said fragrance release half-life is measured in a NaH 2 P0 buffer at said pH.
  • the present invention also relates to perfume and fine fragrances which comprise, in addition to the fragrance delivery systems described herein, other fragrance raw materials and adjunct ingredients.
  • the present invention relates to novel compositions of matter, namely, orthoesters capable of releasing tertiary alcohol fragrance raw materials.
  • this rate of tertiary alcohol release hereinafter known as the "fragrance release half-life"
  • the fragment release half-life can be manipulated in order to provide release of the tertiary alcohol in a manner which corresponds to the specific requirements of a fragrance containing composition.
  • tertiary fragrance raw material releasing compounds are referred to throughout the present specification as pro-perfumes, pro-fragrances, or, preferably, as pro-accords, and these terms are used collectively and/or interchangeably to signify orthoesters capable of releasing at least one tertiary alcohol fragrance raw material.
  • perfume and fine fragrance are essentially synonymous and are used collectively or interchangeably throughout the present specification and are taken to mean the more concentrated forms of fragrance- containing compositions. Aspects of the present invention which apply to “perfumes” will therefore apply equally to “fine fragrances” and vice versa.
  • colognes, eau de toilettes, after shaves, and other fragrance-containing embodiments are perfumes or fine fragrances which have a greater degree of dilution, usually by a volatile carrier such as ethanol.
  • fragrance delivery systems of the present invention comprise at least one pro-accord capable of releasing at least one tertiary alcohol as well as one or more other "pro-accords” which are preferably capable of releasing a mixture of fragrance raw materials or "accords".
  • fragment raw materials are herein defined as compounds preferably have a molecular weight of at least 100 g/mol and which are useful in imparting an odor, fragrance, essence, or scent either alone or in combination with other "fragrance raw materials".
  • fragment raw material relates to tertiary alcohol-releasing pro-accords
  • the molecular weight of adjunct alcohols, which together with the tertiary alcohols form the pro-accord may have molecular weights less than 100 g/mol.
  • lower molecular weight alcohols inter alia ethanol may be used as an orthoester alcohol component in order to produce the desired fragrance release half-life.
  • the "fragrance raw materials" which make up the non-tertiary alcohol- releasing pro-accords of the fragrance delivery systems of the present invention comprise inter alia alcohols, ketones, aldehydes, esters, ethers, nitriles, and alkenes such as terpenes.
  • a listing of common "fragrance raw materials” can be found in various reference sources, for example, “Perfume and Flavor Chemicals", Vols. I and II; Steffen Arctander Allured Pub. Co. (1994) and "Perfumes: Art, Science and Technology”; Muller, P. M. and Lamparsky, D., Blackie Academic and Professional (1994) both incorporated herein by reference.
  • substituted or unsubstituted alkyleneoxy units are defined as moieties having the formula:
  • R * is hydrogen, methyl, and mixtures thereof
  • R" is hydrogen, methyl, ethyl, and mixtures thereof
  • the index x is from 1 to about 20.
  • substituted or unsubstituted alkyleneoxyalkyl are defined as moieties having the formula:
  • R6 (CHiCHO CH j ⁇ wherein R ⁇ is hydrogen, C j -Ci g alkyl, and mixtures thereof; R ⁇ is hydrogen, methyl, ethyl, and mixtures thereof; the index x is from 1 to about 20 and the index y is from 2 to about 18.
  • substituted or unsubstituted alkylenearyl units are defined as moieties having the formula:
  • R ⁇ and R" are each independently hydrogen, hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C]-C 12 linear or branched alkyl), amino, alkylamino, and mixtures thereof, p is from 1 to about 14. 6
  • substituted or unsubstituted alkyleneoxyaryl - units are defined as moieties having the formula:
  • R * and R" are each independently hydrogen, hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C ⁇ -C 12 linear or branched alkyl), amino, alkylamino, and mixtures thereof, q is from 1 to about 14.
  • pro-accords of the present invention which release at least one tertiary alcohol fragrance raw material have the formula:
  • Each R 1 , R 2 , and R 3 is independently substituted or unsubstituted C ⁇ -C 20 linear alkyl, C3-C 2 0 branched alkyl, C3-C20 cyclic alkyl, C 4 -C o branched cyclic alkyl, C3-C20 linear alkenyl, C 4 -C 2 o branched alkenyl, C3-C 2 0 cyclic alkenyl, C 4 -C 2 o branched cyclic alkenyl, C ⁇ - C20 aryl, C6-C 2 0 alkylenearyl, C 6 -C 2 o alkyleneoxyalkyl, C6-C20 alkyleneoxyaryl, and mixtures thereof; preferably substituted or unsubstituted C 1 -C 10 linear alkyl, C 3 -C 1 0 branched alkyl, C 3 - C10 cyclic alkyl, C -C] branched cyclic
  • Non-limiting examples of tertiary alcohol fragrance raw materials include a,a- dimethyl phenethyl alcohol (dimethyl benzyl carbinol), a,a-4-trimethyl-3-cyclohexene-l- methanol (a-terpineol), a,a-4-trimethyl benzene ethanol (p-methyl dimethyl benzyl carbinol), 2-(4-methylphenyl)-2-propanol (Cymenol), 2-methyl-4-phenyl-2-butanol (phenyl ethyl dimethyl carbinol), 3-methyl-l-phenyl-3-pentanol (phenylethyl methylethyl carbinol), 1,2- dimethyl-3-(l-methylethenyl) cyclopentanol (plinol), l,2-dimethyl-3-(l-methylethenyl) cyclohexanol l-methyl-4-isopropyl cycl
  • Non-limiting examples of preferred tertiary alcohol fragrance raw materials include R 1 , R 2 , and R 3 units which are linalyl, tetrahydrolinalyl, ethyllinalyl, dihydromyrcenyl, and mixtures thereof resulting in the release of linalool, tetrahydrolinalool, ethyllinalool, and dihydromyrcenol .
  • R is hydrogen, substituted or unsubstituted C ⁇ -C 2 o linear alkyl, C3-C 2 0 branched alkyl, C3-C 2 0 cyclic alkyl, C -C 20 branched cyclic alkyl, C3-C20 linear alkenyl, C 4 -C 2 o branched alkenyl, C 3 -C 2 o cyclic alkenyl, C -C 2 o branched cyclic alkenyl, C 6 -C 2 o aryl, C 6 -C o alkylenearyl, C 6 -C2o alkyleneoxyalkyl, C 6 -C 2 o alkyleneoxyaryl, and mixtures thereof; or any R 1 , R 2 , or R 3 can be taken together with R to form a ring having from 5 to 8 atoms, said ring is optionally further substituted by one or more C 1 -C 22 alkyl, C 1 -C 22 alken
  • R is hydrogen, substituted or unsubstituted C1-C10 linear alkyl, C3-C 1 0 branched alkyl, C3-C 1 0 linear alkenyl, C 6 -C ⁇ o aryl, C ⁇ -Cio alkylenearyl; more preferably R is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, benzyl, and mixtures thereof.
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C 1 -C j 2 linear or branched alkyl), amino, C ⁇ -C j2 mono- and dialkylamino, and mixtures thereof.
  • the present invention further relates to fragrance delivery systems comprising: a) at least one tertiary alcohol fragrance raw material-releasing pro-accord as described herein; and b) the balance one or more pro-accords suitable for use in delivering one or more fragrance raw materials.
  • the tertiary alcohol fragrance raw material-releasing orthoesters of the present invention When formulated into a fragrance delivery system, will comprise from about 0.1% to about 99%, preferably from about 1 % to about 50% by weight, of said fragrance delivery system.
  • the fragrance delivery systems of the present invention preferably comprise one or more pro-accords described herein below.
  • said pro-accords comprise, alone or as an admixture, from 0.1% to about 99%, preferably from about 1% to about 50% by weight, of the fragrance delivery system.
  • the present invention further relates to a perfume or fine fragrance for application to human skin having increased fragrance longevity comprising: a) from 0.1% to 99.9% by weight, of at least one pro-accord which releases a tertiary alcohol fragrance raw material, provided said pro-accord has a fragrance release half-life of greater than or equal to 0.1 hours at pH 5.3 and less than or equal to 12 hours at pH 2.5 when said fragrance release half-life is measured in a NaH 2 P0 4 buffer at said pH; b) from 0.1% to 99.9% by weight, of one or more fragrance raw materials; and 9
  • perfume or fine fragrance compositions of the present invention further comprise carriers, fixatives, and other adjunct ingredients which can be added in any suitable amount or ratio to the tertiary alcohol-releasing orthoesters or the pro-accords which comprise the balance of the delivery system.
  • Typical carriers are methanol, ethanol
  • Adjunct ingredients include perfume raw material components which are essential oils and are therefore not a single chemical entity.
  • the adjunct ingredients may be mixtures of synthetic fragrance raw materials which serve a further purpose in addition to providing a pleasurable odor.
  • One class of preferred compounds useful as pro-accords according to the present invention are orthoesters having the formula:
  • R is hydrogen, substituted or unsubstituted C ⁇ -C 2 o linear alkyl, C3-C 2 0 branched alkyl, C3-C 2 0 cyclic alkyl, C 4 -C 2 o branched cyclic alkyl, C 3 -C 20 linear alkenyl, C 4 -C 2 o branched alkenyl, C3-C 2 0 cyclic alkenyl, C 4 -C 2 o branched cyclic alkenyl, C6-C 2 0 aryl, C 6 -C 2 o alkylenearyl, C 6 -C 2 o alkyleneoxyalkyl, C 6 -C 2 o alkyleneoxyaryl, and mixtures thereof; preferably hydrogen, substituted or unsubstituted CpCio linear alkyl, C3-C 1 0 branched alkyl
  • Each R 1 , R 2 , and R 3 is independently substituted or unsubstituted C1-C20 linear alkyl, ⁇ C3-C 2 0 branched alkyl, C3-C20 cyclic alkyl, C -C 2 o branched cyclic alkyl, C3-C 2 o linear alkenyl, C 4 -C 2 o branched alkenyl, C3-C20 cyclic alkenyl, C 4 -C 2 o branched cyclic alkenyl, C 6 - C 2 o aryl, C 6 -C 2 o alkylenearyl, C 6 -C 20 alkyleneoxyalkyl, C6-C20 alkyleneoxyaryl, and mixtures thereof; preferably substituted or unsubstituted C 1 -C10 linear alkyl, C3-C 1 0 branched alkyl, C 3 - C10 cyclic alkyl, C 4 -C ⁇ o branche
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; - C0 H; -C0 2 R'; -CONH 2 ; -CONHR'; -CONR' 2 ; wherein R' is C j -C 12 linear or branched alkyl), amino, C j -C j2 mono- and dialkylamino, and mixtures thereof.
  • Another class of compound useful as pro-accords according to the present invention are acetals and ketals having the formula:
  • R is Cj-C 2 o linear alkyl, C3-C 2 Q branched alkyl, C3-C 2 Q cyclic alkyl, C4-C 2 ⁇ branched cyclic alkyl, C3-C 2 n linear alkenyl, C3-C 2 n branched alkenyl, C3-C 2 n cyclic alkenyl, C4-C 2 n branched cyclic alkenyl, Cg-C 2 o substituted or unsubstituted aryl, preferably the moieties which substitute the aryl units are alkyl moieties, and mixtures thereof.
  • Rl is hydrogen, R, or in the case wherein the pro-accord is a ketal, R and R can be taken together to form a ring.
  • R ⁇ and R 3 are independently selected from the group consisting of C5-C n linear, branched, or substituted alkyl; C4-C 2 Q linear, branched, or substituted alkenyl; C5-C 2 ⁇ substituted or unsubstituted cyclic alkyl; Cg-C ⁇ substituted or unsubstituted aryl, C -C4 ⁇ substituted or unsubstituted alkyleneoxy; C3-C40 substituted or unsubstituted alkyleneoxyalkyl; C6-C40 substituted or unsubstituted alkylenearyl; Cg-C3 substituted or unsubstituted aryloxy; C6-C40 substituted or unsubstituted alkyleneoxyaryl;
  • C6-C40 oxyalkylenearyl and mixtures thereof.
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR';
  • orthocarbonates Another class of preferred compounds useful as pro-accords according to the present invention are orthocarbonates having the formula:
  • R , R 2 , R 3 , and R4 are independently C j -C 2 ⁇ linear, branched, or substituted alkyl; C 2 -C 2 ⁇ linear, branched, or substituted alkenyl; C3-C 2 ⁇ substituted or unsubstituted cyclic alkyl; Cg-C 2 ⁇ substituted or unsubstituted aryl, C 2 -C4 ⁇ substituted or unsubstituted alkyleneoxy; C3-C40 substituted or unsubstituted 12
  • alkyleneoxyalkyl C6-C40 substituted or unsubstituted alkylenearyl; C6-C32 substituted or unsubstituted aryloxy; C6-C40 substituted or unsubstituted alkyleneoxyaryl; C6-C40 oxyalkylenearyl; and mixtures thereof.
  • substituted herein is meant "compatible moieties which replace a hydrogen atom".
  • substituents are hydroxy, nitrilo, halogen, nitro, carboxyl (-CHO; -C0 2 H; -C0 2 R'; -CONH 2 ; -CONHR'; -
  • R' is C j -C ⁇ 2 linear or branched alkyl), amino, C j -C ⁇ mono- and dialkylamino, and mixtures thereof.
  • Non-limiting examples of fragrance raw material alcohols which can be suitably released by the pro-accords of the present invention include 2,4-dimethyl-3-cyclohexene-l- methanol (Floralol), 2,4-dimethyl cyclohexane methanol (Dihydro floralol), 5,6-dimethyl-l- methylethenylbicyclo-[2.2.
  • esters suitably released by the pro-accords of the present invention include geranyl formate, citronellyl formate, phenylethyl formate, phenoxyethyl formate, tr ⁇ ?-2-hexenyl formate, c/.s-3-hexenyl formate, cw-6-nonenyl formate, 9-decenyl formate, 3,5,5-trimethylhexyl formate, 3-methyl-5-phenylpentanyl formate, 6-methylheptan- 2-yl formate, 4-(2,2,6-trimethyl-2-cyclohexen-l-yl)-3-buten-2-yl formate, 3-methyl-5-(2,2,3- trimethyl-3-cyclopenten-l-yl)-4-penten-2-yI formate, 4-isopropylcyclohexyleth-2-yl formate, 6,8-dimethylnonan-2-yl formate, decahydro-
  • Non-limiting examples of aldehydes which are released by the pro-accords of the present invention include phenylacetaldehyde, p-methyl phenylacetaldehyde, p-isopropyl phenylacetaldehyde, methylnonyl acetaldehyde, phenylpropanal, 3-(4-t-butylphenyl)-2- methyl propanal (Lilial), 3-(4-t-butylphenyl)-propanal (Bourgeonal), 3-(4-methoxyphenyI)-2- methylpropanal (Canthoxal), 3-(4-isopropylphenyl)-2-methylpropanal (Cymal), 3-(3,4- methylenedioxyphenyl)-2-methylpropanal (Helional), 3-(4-ethylpheny)-2,2-dimethylpropanal (Floralozone), phenylbutanal, 3-methyl-5-phenylpentan
  • ketones which are released by the pro-accords of the present invention include a-damascone, b-damascone, d-damascone, b-damascenone, muscone, 6,7-dihydro-l,l,2,3,3-pentamethyl-4(5H)-indanone (cashmeran), -jasmone, dihydrojasmone, a-ionone, b-ionone, dihydro-b-ionone, g-methyl ionone, a-w ⁇ -methyl ionone, 4-(3,4-methylenedioxyphenyl)butan-2-one, 4-(4-hydroxyphenyl)butan-2-one, methyl b- naphthyl ketone, methyl cedryl ketone, 6-acetyl-l,l,2,4,4,7-hexamethyltetralin (tonalid), /- 16
  • the tertiary alcohol-releasing pro-perfumes hydrolyze upon contact with human skin to release fragrance raw materials.
  • the pro-accords must release their perfume ingredients at a rate useful for providing a sustainable fragrance level.
  • pro-accords can be evaluated in a manner not involving contact with human skin, a method which directly indicates their suitability for use as tertiary alcohol-releasing pro-accords. This procedure also is applicable to all pro-perfumes suitable for use in the fragrance delivery systems of the present invention.
  • pro-accords which have a "Fragrance
  • Pro-accords deliver their corresponding mixture of fragrance raw materials or fragrance accords according to the equation:
  • Pro-Accord * ⁇ Accord wherein the accord which is released, may in some instances comprise a single fragrance raw material, but is preferably a binary accord or a multiple fragrance raw material accord.
  • the rate at which the accord is released is defined by the formula: 17
  • Rate k[Pro-accord] and can be further expressed by the formula:
  • the phosphate buffered water is prepared by admixing 3.95 mL of 85% phosphoric acid (H3PO4) and 24 g of sodium dihydrogen phosphate (NaH 2 P ⁇ 4) with one liter of water. The pH of this solution is approximately 2.5. Next 10 mL of the phosphate buffer is admixed with 90 mL of dioxane and the pro-fragrance to be analyzed is added. The hydrolysis kinetics are then monitored by conventional HPLC at 30° C.
  • the orthoester bis(n-pentyl)dihydromyrcenyl orthoformate has a fragrance release half-life, as measured at pH 5.3 under the above described conditions, of approximately 1.3 hrs and is, therefore, a suitable orthoester for delivering the tertiary alcohol dihydromyrcenol and for use in the fragrance delivery systems of the present invention.
  • an acid catalyst for example, 2,4,6-trimethylbenzoic acid, 2,6-dichlorobenzoic acid, or tetrabutylammonium hydrogen sulfate, 1-2 mol %
  • reaction mixture is then diluted with 2 volumes of ether, washed with a saturated solution of sodium carbonate, dried, evaporated, and subjected to 18 flash chromatography to afford analytically pure bis(phenylethyl)mono(dihydromyrcenol)orthoformate.
  • fragrance delivery system of the present invention is an example of the fragrance delivery system of the present invention.
  • Ethanol carrier contains less than 1% water.
  • Fragrance raw material base, middle and top notes which includes polyethylene glycol as carrier and anhydrous ethanol as a diluent.

Abstract

Cette invention se rapporte à des pro-parfums utilisés pour diffuser sur la peau d'une personne des substances brutes de fragrances à base d'alcools tertiaires. Cette invention se rapporte également à des systèmes de diffusion de fragrances qui sont conçus pour être utilisés dans des fragrances fines et dans des compositions de parfums, ces systèmes comprenant au moins un pro-parfum qui diffuse un alcool tertiaire de substance brute de fragrance, le reste étant constitué par d'autre pro-accords.
PCT/US1999/002733 1998-02-24 1999-02-08 Systemes de diffusion de substances brutes de fragrances a base d'alcools tertiaires WO1999043639A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002321846A CA2321846A1 (fr) 1998-02-24 1999-02-08 Systemes de diffusion de substances brutes de fragrances a base d'alcools tertiaires
BR9908220-9A BR9908220A (pt) 1998-02-24 1999-02-08 Sistemas que oferecem matéria-prima de fragância de álcool terciário
JP2000533398A JP2002504532A (ja) 1998-02-24 1999-02-08 三級アルコールフレグランス原料デリバリー系
EP99905882A EP1056702A1 (fr) 1998-02-24 1999-02-08 Systemes de diffusion de substances brutes de fragrances a base d'alcools tertiaires

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US7570998P 1998-02-24 1998-02-24
US60/075,709 1998-02-24

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
WO2000063329A1 (fr) * 1999-04-20 2000-10-26 The Procter & Gamble Company Aldehydes utiles en tant que matieres brutes de parfum et precurseurs de parfum contenant un atome de carbone alpha tertiaire
EP1116788A1 (fr) * 2000-01-12 2001-07-18 The Procter & Gamble Company Composition de pro-parfum
US7569529B2 (en) 2005-09-07 2009-08-04 The Procter & Gamble Company Method of using fabric care compositions to achieve a synergistic odor benefit
JP2015537064A (ja) * 2012-10-08 2015-12-24 ディーエスエム アイピー アセッツ ビー．ブイ． 香味香気配合物（ｉｖ）

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WO1994006441A1 (fr) * 1992-09-22 1994-03-31 The Mennen Company Composition contenant une fragrance activee par le corps destinee a etre appliquee sur la peau et son procede d'utilisation
WO1998047477A1 (fr) * 1997-04-24 1998-10-29 The Procter & Gamble Company Precurseurs d'accords de parfum
WO1998047478A1 (fr) * 1997-04-24 1998-10-29 The Procter & Gamble Company Parfums ayant des caracteristiques de longevite d'odeur

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Publication number Priority date Publication date Assignee Title
WO1994006441A1 (fr) * 1992-09-22 1994-03-31 The Mennen Company Composition contenant une fragrance activee par le corps destinee a etre appliquee sur la peau et son procede d'utilisation
WO1998047477A1 (fr) * 1997-04-24 1998-10-29 The Procter & Gamble Company Precurseurs d'accords de parfum
WO1998047478A1 (fr) * 1997-04-24 1998-10-29 The Procter & Gamble Company Parfums ayant des caracteristiques de longevite d'odeur

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000063329A1 (fr) * 1999-04-20 2000-10-26 The Procter & Gamble Company Aldehydes utiles en tant que matieres brutes de parfum et precurseurs de parfum contenant un atome de carbone alpha tertiaire
EP1116788A1 (fr) * 2000-01-12 2001-07-18 The Procter & Gamble Company Composition de pro-parfum
WO2001051599A1 (fr) * 2000-01-12 2001-07-19 The Procter & Gamble Company Composition precurseur de parfum
US7569529B2 (en) 2005-09-07 2009-08-04 The Procter & Gamble Company Method of using fabric care compositions to achieve a synergistic odor benefit
JP2015537064A (ja) * 2012-10-08 2015-12-24 ディーエスエム アイピー アセッツ ビー．ブイ． 香味香気配合物（ｉｖ）

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EP1056702A1 (fr) 2000-12-06
CN1298378A (zh) 2001-06-06
CA2321846A1 (fr) 1999-09-02
BR9908220A (pt) 2000-10-24

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