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Europäisches Patentamt *EP000983043B1*
(19) European Patent Office
Office européen des brevets (11) EP0 983 043 B1
(12) EUROPEAN PATENT SPECIFICATION
(45) Date of publication and mention 7
(51) Int Cl. : A61K 7/46, A61K 7/48
of the grant of the patent:
25.06.2003 Bulletin 2003/26 (86) International application number:
PCT/GB98/01381
(21) Application number: 98921611.4
(87) International publication number:
(22) Date of filing: 14.05.1998 WO98/052527 (26.11.1998Gazette 1998/47)
(54) PERFUME FIXATIVES COMPRISING POLYVINYLPYRROLIDONE AND HYDROXYPROPYL
CELLULOSE
RIECHSTOFFFIXIERMITTEL DIE POLYVINYLPYRROLIDON UND HYDROXYLCELLULOSE
ENTHALTEN
FIXATEURS DE PARFUMS COMPRENANT DE LA POLYVINYLPYRROLIDONE ET DE
L’HYDROXYPROPYLE CELLULOSE
(84) Designated Contracting States: • DATABASE WPI Week 8524 Derwent
DE ES FR GB GR IT NL Publications Ltd., London, GB; AN 85-144086
XP002043727 "Giving strong scent to
(30) Priority: 21.05.1997 EP 97303459 insecticidal para-dichlorobenzene - using
perfume soln. of PVP or hydroxypropyl
(43) Date of publication of application: cellulose" & JP 60 078 926 A (DAIHO KORYO) ,
08.03.2000 Bulletin 2000/10 4 May 1985
• DATABASE WPI Week 8726 Derwent
(73) Proprietor: QUEST INTERNATIONAL B.V. Publications Ltd., London, GB; AN 87-183168
1411 GP Naarden (NL) XP002043728"Prepn.oflong-lastingfragnance
- contg. hydroxypropylcellulose ethanol and/or
(72) Inventors: methanol soln. and vinylpyrrolidone" & JP 62
• PERRING, Keith, Douglas 114909A(NIPPONEKISHO),26May1987cited
Kent TN24 8HS (GB) in the application
• IRVING, Pamela, Virginia • DATABASE WPI Week 9511 Derwent
Kent CT19 6JA (GB) Publications Ltd., London, GB; AN 95-078134
• NESS, Jeremy, Nicholas XP002043729 "Resin compsn contg. aromatic
Ashford, Kent TN25 4DQ (GB) component for imparting aroma to e.g.
• TUCK, Kathleen, Mary perfume-advertising goods - comprises
Ashford, Kent TN24 8YD (GB) water-soluble resin e. g. CMC, solvent for resin
and aromatic component enclosed in
(74) Representative: Matthews, Heather Clare et al microcapsule" & JP 07 003 075 A (DAINIPPON
Keith W Nash & Co PRINTING & INCTEC) , 6 January 1995
Pearl Assurance House • DATABASE WPI Week 8747 Derwent
90-92 Regent Street Publications Ltd., London, GB; AN 87-331354
Cambridge CB2 1DP (GB) XP002043730"Water-absorptivecompsn.contg.
perfume-comprisesperfumecoatedwithwater
(56) References cited: solubleresinpowderandwaterabsorptiveresin
• DATABASE WPI Week 8540 Derwent powder" & JP 62 236 860 A (SEITETSU) , 16
Publications Ltd., London, GB; AN 85-247016 October 1987
B1 XP002043726 "Flavouring camphor or
naphthalene - by adding perfume contg.
dissolvedPVPorhydroxypropylcellulose"&JP
60 163 802 A (DAIHO KORYO) , 26 August 1985
Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give
0 983 043notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in
a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art.
EP 99(1) European Patent Convention).
Printed by Jouve, 75001 PARIS (FR)
EP0 983 043 B1
Description
Field of the Invention
5 [0001] This invention concerns perfume fixatives, that is, compositions intended for use in perfume-containing for-
mulationstoenhancefragrancelife.Thewords"perfume"and"fragrance"areusedsynonymouslyinthisspecification
and no significance should be attached to the choice of word used in any particular context. The invention includes
withinitsscopeperfumefixatives,mixturesofperfumeandfixative,mixturesofproductbaseandfixative,andperfumed
products including perfume and fixative.
10
Background to the Invention
[0002] Fragrances in some products such as perfumed leave-on skin products, particularly (but not exclusively)
ethanol-based ones eg (deo)colognes, personal perfumes, anti-perspirant deodorants, hair colognes etc, tend to lose
15 their character rapidly ie the top/middle notes evaporate. There is a desire to extend the life of such perfumes, partic-
ularly in retaining the initial character and intensity of the fragrance, and variousperfumefixativeshavebeenproposed.
It is an important practical consideration that the fixative should not adversely affect the aesthetic character of the
product, ie the fixative should not be discernible by the user.
20 Prior Art
[0003] Various fixative systems have been proposed including fixative oils (eg GLUCAM P20 (GLUCAM is a Trade
Mark))orfilm-formingpolymers.Theformerrequiretheuseofrelativelyhighlevelsofoiltoproducenoticeableeffects,
whilstwhenthelatterareeffectivetheyproduceverynoticeablefilms(bothvisualandtactile).Variousperfumecarriers/
25 encapsulates have also been proposed but suffer from problems with cost and visibility in the product and/or on the
skin/hair. JP 62114909 discloses use of 1 to 60 wt% of polyvinylpyrrolidone (PVP) and 1 to 30 wt% of hydroxypropyl
cellulose (HPC) with a fragrance material to produce a long lasting fragrance. Such levels of PVP and HPC would be
very readily noticeable to the consumer.
30 Summary of the Invention
[0004] In one aspect the present invention provides a perfume fixative comprising:
(a) polyvinylpyrrolidone;
35 (b) hydroxypropyl cellulose; and
(c) hydrophobic oil comprising one or more selected from the following:
propyleneglycoldicaprate/dicaprylate, ie C8,C10 diester with propylene glycol, eg as MIGLYOL 840 (MIGLY-
OL is a Trade Mark) from Huls;
40 dioctyl adipate;
isopropyl myristate;
glycerol monooleate;
POE(10) cetyl ether;
POE(20) sorbitan monolaurate;
45 dibutyl phthalate; and
acetyl tributyl citrate.
[0005] POE is an abbreviation for poly(oxyethylene) ether.
[0006] The currently preferred material is MIGLYOL 840.
50 [0007] A mixture of hydrophobic oils may be used.
[0008] Polyvinylpyrrolidone (PVP) is readily commercially available in a range of molecular weights. The molecular
weight of the PVP is not critical, but in general it is thought that PVP of higher molecular weights gives better perform-
ance. Good results have been obtained with the high molecular weight PVP LUVISKOL K90 (LUVISKOL is a Trade
Mark) from BASF. A mixture of different PVPs may be used.
55 [0009] Hydroxypropyl cellulose (HPC) is similarly readily commercially available in a range of molecular weights.
HighermolecularweightHPCgivesbetterperformancebutalsohasathickeningeffect,soitispreferredtousemedium
molecular weight HPCs as a compromise between performance and product compatibility. Good results have been
obtained with KLUCEL G (KLUCEL is a Trade Mark) from Aqualon. A mixture of different HPCs may be used.
2
EP0 983 043 B1
[0010] The hydrophobic oil should be non-ionic oil which is liquid at skin temperature (typically about 35°C under
normal conditions).
[0011] Thehydrophobicoilsuitablyhasanoctanol/waterpartitionco-efficient(logP)greaterthan3,preferablygreater
than 5.
5 [0012] The hydrophobic oil suitably has a Hildebrand's solubility parameter (δ ) (Hildebrand, J.H. & Scott, R.L.
HILD
υ
TheSolubility of Nonelectrolytes, 3rd edition, Reinhold, New York, 1950) of less than 20 MPa , and preferably greater
υ
than 14 MPa .
[0013] Forobviousreasons,thehydrophobicoilshouldbeodourless,oflowodour,orofneutralorinoffensiveodour.
[0014] The hydrophobic oil should also be non-volatile, preferably having a vapour pressure of less than about
10 0.01mm Hg.
[0015] Thehydrophobicoilispreferablyanesterand/or(poly)ether.Estersarecurrentlythemostpreferredmaterials.
[0016] The proportions of the 3 ingredients in the fixative are not critical.
[0017] Preferably the PVP and HPCtogetherconstituteat least 30%, more preferably at least 40%, by weight of the
total weight of the fixative.
15 [0018] The oil preferably constitutes at least 10% by weight of the total weight of the fixative.
[0019] Thecompositiontypically comprises equal amounts by weight of PVP and HPC but this is not essential, and
there may be cases where it is advantageous for the amount by weight of the HPC to exceed that of PVP.
[0020] Goodresults have been obtained with fixatives comprising, by weight, 25% PVP, 25% HPC and 50% hydro-
phobic oil.
20 [0021] A typical fixative formulation consists of:
MIGLYOL 840 50.0 wt% non-volatile oil
LUVISKOL K90 25.0 wt% PVP, high molecular weight
KLUCEL G 25.0 wt% HPC, medium molecular weight
25
[0022] Theperfumefixativeisusedbybeingincorporatedinaperfume-containingformulationorproduct.Thefixative
is found to be effective in enhancing perfume life, even when the fixative is used at low levels. The efficacy even at
low levels is surprising and unexpected, and the reason for this efficacy is not yet known.
30 [0023] Forpractical reasons, the PVP and HPCtogethershouldnotconstitutemorethanabout0.5%,preferablynot
more than about 0.25%, by weight of the perfume-containing product. If these materials are present at higher levels
theyarediscerniblebytheuser,eitherbysightorfeel,whichisundesirable.However,thefixativeisfoundtobeeffective
in an amount corresponding to this constraint and also at lower levels.
[0024] Forexample,foraperfumedproductcontaining1%byweightperfume(whichistypicaloftheperfumelevels
35 in a deodorant), a perfume:fixative weight ratio of at most 2:1 satisfies the above preferred constraint (for a fixative
comprising 50% by weight PVP and HPC), and this is found to be more than adequate to obtain good results. Indeed,
useful effects are obtained with considerably smaller amounts of fixative, eg with perfume:fixative weight ratios of 9:1
or even 19:1 which correspond to combined PVP and HPC weights of 0.055% and 0.026%, respectively (for a fixative
comprising 50% by weight PVP and HPC).
40 [0025] For perfumed products with higher perfume levels, such as personal perfumes and fine fragrances which
typically contain perfume in an amount in the range 2 to 25% by weight, even higher perfume:fixative weight ratios can
be effective.
[0026] Themosteffective level of the fixative depends upon the nature of the perfume and the amount in which it is
used, and this can be determined by experiment.
45 [0027] The fixative may be used with a wide range of perfumes, although best results are obtained with perfumes
that are not very substantive, ie those perfumes that are most in need of improvement.
[0028] For incorporation in a perfume or perfumed product, the fixative may be pre-mixed with perfume and then
addedtoproductbase(whichisallproductingredientsexceptperfume).Alternativelythefixativemaybeaddedtothe
perfumed product (ie product base and perfume). As a further possibility, the fixative may be added to the product
50 base, and perfume then added.
[0029] In a further aspect, the invention thus provides perfume mixed with perfume fixative in accordance with the
invention.
[0030] The invention also covers a product base mixed with perfume fixative in accordance with the invention.
[0031] Another aspect of the invention covers a perfumed product comprising perfume fixative in accordance with
55 the invention.
[0032] The invention is applicable to a wide range of perfumed products where fragrance life is a consideration,
including perfumed leave-on skin products, including ethanol-, water- and silicone-based products, such as colognes,
deo-colognes, personal perfumes, deodorant, anti-perspirant deodorants, hair colognes etc.
3
EP0 983 043 B1
[0033] A typical deodorant has the following composition:
Ethanol 80.0 wt%
Water to 100.0 wt%
5 Fragrance 1.00 wt%
Fixative Blend 0.50 wt%
Triclosan 0.25 wt%
10 [0034] Thefixative conveniently comprises, by weight, 50% MIGLYOL 840, 25% LUVISKOLK90and25%KLUCEL
G, as discussed above.
[0035] Theinvention also includes use of a perfume fixative in accordance with the invention, comprising preparing
aperfumedleave-on skin product containing said perfume fixative and applying said perfumed leave-on skin product
to humanskin.Alsocoveredisamethodofpreparingaperfumeorperfumedproduct,comprisingpreparingaperfume
15 fixative in accordance with the invention and mixing said perfume fixative with a perfume.
[0036] The invention will be further described, by way of illustration, in the following Examples.
Example 1 (Cologne)
20 [0037] Thefollowingexampleillustratestheimprovementinperformancethatcanbeproducedusingaclassiccitrus
cologne perfume. The perfume tested comprised the following ingredients:
Citrus Cologne Perfume A wt%
Nonanal 0.2
25 Decanal 0.4
Benzyl Acetate 5.0
Camphor 0.4
Cineole 0.4
30 Citral Lemarome 0.7
Geraniol 5.0
Hydroxycitronellal 2.0
Limonene Dextro 40.0
Linalol 10.0
35 Linalyl Acetate 16.0
Lyral (IFF) 2.0
Methyl Dihydro Jasmonate Super (Q) 2.0
Myrcenyl Acetate 3.0
40 Terpinyl Acetate 12.9
(G) - Givaudan-Roure SA
(Q) - Quest
[0038] Three colognes were prepared by simple mixing as follows:
45
wt% Reference Test1 Test2 Test3
Citrus Cologne Perfume 2.0 2.0 2.0 2.0
Ethyl alcohol 79.6 78.8 78.8 78.8
50 Distilled water 18.4 18.2 18.2 18.2
LUVISKOL K90 - 0.25 0.25 0.5
KLUCEL G - 0.25 0.25 0.5
MIGLYOL 840 - 0.50 - -
MYVEROL 18-99 - - 0.50 -
55
[0039] MYVEROL18-99(MYVEROLisaTradeMark)is mainly glycerol mono-oleate and is available from Quest
International.
4
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