(19) United States
`(12) Patent Application Publication (10) Pub. No.: US 2006/0178290 A1
`Bara
`(43) Pub. Date:
`Aug. 10, 2006
`
`US 20060178290A1
`
`(54) PERFUME COMPOSITION
`
`(30)
`
`Foreign Application Priority Data
`
`(75) Inventor: Isabelle Bara, Hilaire (FR)
`
`Jul. 8, 2003
`
`(FR) ............................................ .. 0308323
`
`Correspondence Address:
`OBLON, SPIVAK, MCCLELLAND, MAIER &
`NEUSTADT, RC.
`1940 DUKE STREET
`ALEXANDRIA, VA 22314 (Us)
`
`Publication Classi?cation
`
`(51) Int. Cl.
`(2006.01)
`A61Q 13/00
`(52) US. Cl. ................................................................ .. 512/2
`
`(73) Assignee: L’OREAL, Paris (FR)
`(21) Appl. No.:
`10/563,967
`
`(22) PCT Filed:
`(86) PCT NO _
`"
`Related US Application Data
`
`Jun‘ 24’ 2004
`P CT IEPO 4 I0 6902
`
`(60) Provisional application No. 60/490,255, ?led on Jul.
`28, 2003.
`
`(57)
`
`ABSTRACT
`
`The present invention relates to a perfume composition
`comprising a mixture of fragrant materials in a physiologi
`cally acceptable carrier comprising a mixture of polydim
`ethyls'iloxanes, characterized in that the said mixture of
`polydimethylsiloxanes consists of hexamethyldlsiloxane
`and octamethyltrisiloxane, in a Weight ratio Of between
`30:70 and 70:30.
`
`AQUESTIVE EXHIBIT 1038 page 0000
`
`

`

`US 2006/0178290 A1
`
`Aug. 10, 2006
`
`PERFUME COMPOSITION
`
`[0001] The present invention relates to novel perfume
`compositions comprising a mixture of fragrant materials in
`a physiologically acceptable carrier comprising a mixture of
`polydimethylsiloxanes, characterized in that the said mix
`ture of polydimethylsiloxanes consists of hexamethyldisi
`loxane and octamethyltrisiloxane in a hexamethyldisiloxane
`to octamethyltrisiloxane Weight ratio ranging from 30:70 to
`70:30.
`[0002] The perfume compositions usually comprise a mix
`ture of fragrant materials having a vapour pressure less than
`atmospheric pressure at 25° C. and are generally liquid at
`25° C., but sometimes also solid, in a physiologically
`acceptable medium based on ethanol and optionally Water.
`[0003] Ethanol constitutes a good solubilizing agent for
`perfuming ingredients, and additionally has the advantage of
`being inexpensive and of alloWing the formulation of trans
`parent compositions. On the other hand, it has the disad
`vantage of adversely affecting the olfactory characteristics
`of the perfuming ingredients, not only because of its potent
`odour but also because of its capacity to react, in the
`presence of Water, With the perfuming ingredients and to
`thereby modify their odour and/or their colour. It is in
`addition capable of chemically reacting With atmospheric
`nitrogen oxides to form ozone, Which constitutes, in this
`regard, a source of atmospheric pollution Which efforts are
`being made to avoid. Finally, ethanol is an irritant and may
`be a source of tingling When it is applied to a sensitive or
`damaged skin, in particular after shaving.
`[0004] Several attempts have therefore been made to
`replace ethanol in perfume compositions With other solvents
`not having the above disadvantages.
`[0005] A ?rst route consists in replacing ethanol With
`aqueous compositions containing hydrophilic solubilizing
`agents such as polyethoxylated hydrogenated castor oils.
`The compositions obtained contain high percentages of
`these solubilizing agents Which may be irritating, foaming
`and may have a sticky effect on the skin. Another route
`consists in formulating perfume compositions in the form of
`micro- and nanoemulsions. The oily phase of these emul
`sions, containing the perfuming ingredients, is hoWever
`limited in quantity so as not to destabilize the emulsion,
`Which reduces the perfuming effect of these compositions.
`Moreover, the presence of Water in a large quantity is
`capable of causing degradation of the perfuming ingredients
`over time and therefore of adversely affecting the olfactory
`characteristics of the product.
`
`[0006] Another solution further consisted in providing
`perfume compositions in Which the ethanol is at least
`partially replaced by one or more volatile silicones Which
`are lineariof the polydimethylsiloxane type4or cyclic.
`Such is the case in the document WO 99/01106 Which
`discloses perfume compositions intended for impregnating
`textiles or nonWoven fabrics. The document U.S. Pat. No.
`6,432,912 also discloses a perfume composition containing
`these volatile silicones, optionally used in the form of a
`mixture in order to adjust the rate of evaporation of the
`carrier, and Which are combined With cosolvents such as
`esters optionally combined With diesters.
`
`[0007] HoWever, the applicant has noW discovered, sur
`prisingly, that by choosing a particular combination of
`
`silicone compounds not described in the prior art, it Was
`possible to obtain a perfume composition Whose rate of
`evaporation is close to that of ethanol and possessing a ?ash
`point greater than or equal to 00 C., preferably greater than
`or equal to 10° C.
`
`[0008] The subject of the present invention is therefore a
`perfume composition comprising a mixture of fragrant mate
`rials in a physiologically acceptable carrier comprising a
`mixture of polydimethylsiloxanes, characterized in that the
`said mixture of polydimethylsiloxanes consists of hexam
`ethyldisiloxane and octamethyltrisiloxane in a hexamethyl
`disiloxane to octamethyltrisiloxane Weight ratio ranging
`from 30:70 to 70:30.
`[0009] Advantageously, the hexamethyldisiloxane to
`octamethyltrisiloxane Weight ratio ranges from 30:70 to
`40:60. More preferably, the polydimethylsiloxane mixture
`contains 30% by Weight of hexamethyldisiloxane and 70%
`by Weight of octamethyltrisiloxane.
`[0010] The polydimethylsiloxanes according to the inven
`tion are available in particular from the company DOW
`CORNING under the trade name DoW Corning Fluid 200
`0.65 cst and 1 cst, from the company RHODIA under the
`trade name Silbione Huile 70041 0.65 D, from the company
`WACKER under the trade name Belsil DM 0.65 and from
`the company GE BAYER SILICONES under the trade name
`hexamethyldisiloxan.
`[0011] The fragrant materials contained in the perfume
`composition according to the invention are compounds
`Which are customarily used by perfumers and they are
`described in particular in S. Arctander, Perfume and Flavor
`Chemicals (Montclair, N.J., 1969), in S. Arctander, Perfume
`and Flavor Materials of Natural Origin (Elizabeth, N.J.,
`1960) and in “Flavor and Fragrance Materialsi1991”,
`Allured Publishing Co. Wheaton, III. USA.
`[0012] They may be natural products (essential oils, abso
`lutes, resinoids, resins, concretes) and/or synthetic products
`(hydrocarbons, alcohols, aldehydes, ketones, ethers, acids,
`esters, acetals, ketals, nitriles, saturated or unsaturated, ali
`phatic or cyclic).
`
`[0013] Examples of essential oils comprise essential oils
`of lemon, orange, anise, bergamot, rose, geranium, ginger,
`neroli, basil, rosemary, cardamom, camphor, cedar, camo
`mile, sandalWood, sage, and mixtures thereof, Without this
`list being limiting.
`[0014] Examples of other fragrant compounds are in par
`ticular: geraniol, geranyl acetate, farnesol, borneol, bomyl
`acetate, linalol, linalyl acetate, linalyl propionate, linalyl
`butyrate, tetrahydrolinalol, citronellol, citronellyl acetate,
`citronellyl formate, citronellyl propionate, dihydromyr
`cenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpi
`neol, terpinyl acetate, nopol, nopyl acetate, nerol, neryl
`acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl
`alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate,
`benzyl benzoate, amyl salicylate, dimethylbenzylcarbinol,
`trichloromethylphenylcarbinyl acetate, p-tert-butylcyclo
`hexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol,
`alpha-hexylcinnamaldehyde, 2-methyl-3-(p-tert-butylphe
`nyl)-propanal,
`2-methyl-3-(p-isopropylphenyl)propanal,
`3-(p-tert-butylphenyl)propanal,
`2,4-dimethylcyclohex-3
`enylcarboxaldehyde, tricyclodecenyl acetate, tricyclo-dece
`nyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohex
`
`AQUESTIVE EXHIBIT 1038 page 0001
`
`

`

`US 2006/0178290 A1
`
`Aug. 10, 2006
`
`4-(4-methyl-3-pentenyl)-3
`enecarboxaldehyde,
`4-acetoxy-3-pentyltetra
`cyclohexenecarboxaldehyde,
`hydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n
`heptylcyclopentanone,
`3-methyl-2-pentyl-2-cyclo
`pentenone, menthone, carvone, tagetone, geranylacetone,
`n-decanal, n-dodecanal, 9-decen-1-ol, phenoxyethyl isobu
`tyrate, phenylacetaldehyde dimethyl acetal, phenylacetalde
`hyde diethyl acetal, geranonitrile, citronellonitrile, cedryl
`acetate, 3-isocamphylcyclo-hexanol, cedryl methyl ether,
`isolongifolanone, aubepine nitrile, aubepine, heliotropine,
`coumarin, eugenol, vanillin, diphenyl oxide, citral, citronel
`lal, hydroxycitronellal, damascone, ionones,-methylion
`ones, isomethylionones, solanone, irones, cis-3-hexenol and
`its esters, indan musks, tetralin musks, isochroman musks,
`macrocyclic ketones, macrolactone musks, ethylene brassy
`late and mixtures thereof.
`[0015] The composition according to the present invention
`usually contains from 2 to 60% by Weight, and preferably
`from 5 to 40% by Weight, of fragrant materials. It addition
`ally contains a su?icient quantity of polydimethylsiloxanes
`to solubiliZe the fragrant materials, and preferably from 20
`to 99% by Weight of polydimethylsiloxanes, relative to the
`total Weight of the composition.
`[0016] The perfume composition according to the inven
`tion also generally comprises solvents, adjuvants or addi
`tives commonly used in the perfume sector Which do not
`adversely affect the desired olfactory e?‘ect. Preferably,
`hoWever, this composition does not contain an ester of a
`C4-C1O acid and of a C4-Cl5 alcohol.
`[0017] This perfume composition may constitute an eau de
`Cologne, an eau de toilette, a perfume or an aftershave
`lotion.
`
`[0018] Depending on its ?ash point, it may be packaged in
`an atomiZer or possibly in an aerosol device. In the latter
`case, the composition according to the invention addition
`ally contains a propellant gas such as dimethyl ether, pro
`pane, n-butane, isobutane, pentane, trichloro?uoromethane,
`dichlorodi?uoro-methane, chlorodi?uoromethane, 1 ,1 ,1 ,2
`tetra?uoro -ethane, chloropenta?uoroethane, 1 -chloro-1 ,1 -
`di?uoro-ethane, 1,1-di?uoroethane, and mixtures thereof.
`Dimethyl ether, isobutane and 1,1,1,2-tetra?uoroethane are
`preferably used, and preferably isobutane.
`[0019] The invention Will noW be illustrated With the
`folloWing nonlimiting examples. In these examples, the
`quantities are indicated as a percentage by Weight.
`
`EXAMPLES
`
`Example 1
`
`Comparative Study of the Properties of Various
`Mixtures of Silicones
`
`[0020] Various mixtures of silicones Were tested in order
`to evaluate, on the one hand, their rate of evaporation and,
`on the other hand, the ?ash point of a composition com
`prising these mixtures in combination With a perfume.
`a) Protocols
`[0021] Flash Point
`[0022] The test composition is heated in a closed cup of
`standard siZes at a temperature about 3° C. less than the
`
`presumed ?ash point, for 60 seconds. Next, a ?ame of
`standard siZe is introduced into the vapours in the cup
`through a sliding opening. The test is repeated in 1° C. steps.
`The loWest temperature at Which ignition occurs is noted as
`being the ?ash point.
`[0023] The test is carried out in a SETAFLASH apparatus
`according to the ISO 3679 standard.
`[0024] Rate of Evaporation
`[0025] 15 g of solvent to be tested are introduced into a
`crystalliZing dish (diameter: 7 cm) placed on a balance
`Which is in a chamber of about 0.3 m3 Whose temperature
`(25° C.) and humidity (relative humidity: 50%) are regu
`lated.
`[0026] The solvent is alloWed to evaporate freely, Without
`stirring, While ventilating using a ventilator (PAPST-MO
`TOREN, reference 8550 N, revolving at 2700 revolutions/
`min) placed vertically above the crystalliZing dish contain
`ing the solvent, the blades being directed toWards the
`crystalliZing dish and at a distance of 20 cm relative to the
`base thereof.
`
`[0027] The mass of solvent remaining in the crystalliZing
`dish is measured at regular intervals during the ?rst thirty
`minutes of evaporation. The rate of evaporation is expressed
`in mg of solvent evaporated per unit of surface area (cm2)
`and per unit of time (minute).
`b) Results
`[0028] The table beloW groups together the results
`obtained for various combinations of volatile silicones, in
`variable Weight ratios. In this table:
`
`Mixture of silicones
`
`Rate of evaporation
`(mg/cmZ/min)
`
`Flash point*
`(° C.)
`
`30/70
`
`40/60
`55/45
`60/40
`70/30
`
`L2/L3
`L2/L4
`
`L2/L5
`
`L2/L3
`L2/L3
`L2/L3
`L2/L3
`L2/L5
`
`4.23
`3.25
`
`3.39
`
`5.39
`6.98
`j
`8.97
`7.77
`
`+11
`i
`
`i
`
`i
`+2
`+2
`0
`—1
`
`L2 denotes hexamethyldisiloxane
`L3 denotes octrnethyltrisiloxane
`L4 denotes decamethyltetrasiloxane
`L5 denotes dodecalnethylpentasiloxane
`*Compositions comprising from 12 to 17.7% by Weight of per?nne extract
`in the mixture of silicones.
`
`[0029] By Way of comparison, the rate of evaporation of
`ethanol, measured under the same conditions, is 5.13
`mg/cm2/min. The ?ash point of a composition comprising
`12% by Weight of perfume extract in ethanol is 160 C. That
`of a composition comprising 12% by Weight of perfume
`extract in hexamethyldisiloxane is —5° C.
`[0030] As is evident from this table, the mixtures of
`silicones consisting of the silicone L2 combined With
`another silicone chosen from the silicones L4 and L5, in
`Weight ratios ranging from 70:30 to 30:70, do not alWays
`make it possible to obtain compositions having a ?ash point
`greater than 0° C. and a volatility at least equal to 4
`mg/cm2/min, unlike the mixture of silicones according to the
`invention.
`
`AQUESTIVE EXHIBIT 1038 page 0002
`
`

`

`US 2006/0178290 A1
`
`Aug. 10, 2006
`
`Example 2
`
`Perfume Compositions
`
`[0031] The compositions below Were prepared in a con
`ventional manner for persons skilled in the art.
`
`Composition A
`
`Perfume extract “Noa”
`Hexalnethyldisiloxane
`octamethyltrisiloxane
`Composition B
`
`Perfume extract “Emporio White”
`Hexalnethyldisiloxane
`octamethyltrisiloxane
`
`12%
`48.4%
`39.6%
`
`17.7%
`24.7%
`57.6%
`
`1. A perfume composition comprising a mixture of fra
`grant materials in a physiologically acceptable carrier com
`prising a mixture of polydimethylsiloxanes, Wherein the
`mixture of polydimethylsiloxanes comprises hexamethyld
`isiloxane and octamethyltrisiloxane in a hexamethyldisilox
`ane to octamethyltrisiloxane Weight ratio ranging from
`30:70 to 70:30.
`2. The composition according to claim 1, Wherein the
`hexamethyldisiloxane to octamethyltrisiloxane Weight ratio
`ranges from 30:70 to 40:60.
`3. The composition according to claim 1, Wherein the
`mixture of polydimethylsiloxanes comprises 30% by Weight
`of hexamethyldisiloxane and 70% by Weight of octameth
`yltrisiloxane.
`4. The composition according to claim 1, Wherein the
`composition comprises from 5 to 40% by Weight of the
`fragrant materials.
`5. The composition according to claim 1, Wherein the
`composition comprises from 20 to 99% by Weight of a the
`mixture of polydimethylsiloxanes.
`6. The composition according to claim 1, Wherein the
`composition does not comprise an ester of a C4-C 1O acid and
`a C4-Cl5 alcohol.
`
`7. An aerosol device comprising the composition of claim
`1 and a propellant gas.
`8. The composition according to claim 2, Wherein the
`composition comprises from 5 to 40% by Weight of the
`fragrant materials.
`9. The composition according to claim 3, Wherein the
`composition comprises from 5 to 40% by Weight of the
`fragrant materials.
`10. The composition according to claim 2, Wherein the
`composition comprises from 20 to 99% by Weight of the
`mixture of polydimethylsiloxanes.
`11. The composition according to claim 3, Wherein the
`composition comprises from 20 to 99% by Weight of the
`mixture of polydimethylsiloxanes.
`12. The composition according to claim 4, Wherein the
`composition comprises from 20 to 99% by Weight of the
`mixture of polydimethylsiloxanes.
`13. The composition according to claim 2, Wherein the
`composition does not comprise an ester of a C4-C 1O acid and
`a C4-Cl5 alcohol.
`14. The composition according to claim 3, Wherein the
`composition does not comprise an ester of a C4-C 1O acid and
`a C4-Cl5alcohol.
`15. The composition according to claim 4, Wherein the
`composition does not comprise an ester of a C4-C 1O acid and
`a C4-Cl5alcohol.
`16. The composition according to claim 5, Wherein the
`composition does not comprise an ester of a C4-C 1O acid and
`a C4-Cl5 alcohol.
`17. An aerosol device comprising the composition of
`claim 2 and a propellant gas.
`18. An aerosol device comprising the composition of
`claim 3 and a propellant gas.
`19. An aerosol device comprising the composition of
`claim 4 and a propellant gas.
`20. An aerosol device comprising the composition of
`claim 5 and a propellant gas.
`
`AQUESTIVE EXHIBIT 1038 page 0003
`
`