(56) References cited:

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Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent

353

654 B1

TEPZZ ¥5¥654B_T

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EP 2 353 654 B1

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EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention of the grant of the patent: 17.06.2015 Bulletin 2015/25 (21) Application number: 10167914.0 (22) Date of filing: 19.11.2003 (51) Int Cl.: A61K 8/34(2006.01) _{A61K 8/39}(2006.01) A61K 8/41(2006.01) _{A61Q 11/00}(2006.01) A61Q 13/00(2006.01) _{C11B 9/00}(2006.01) C11D 3/50(2006.01) _{A61K 8/42}(2006.01) A61K 8/92(2006.01)

(54) Functional fragrance precursor

Funktionalisierte Reichstoff-Vorprodukte Precurseurs fonctionnels de parfums (84) Designated Contracting States:

AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

(30) Priority: 25.11.2002 US 303287

(43) Date of publication of application: 10.08.2011 Bulletin 2011/32

(62) Document number(s) of the earlier application(s) in accordance with Art. 76 EPC:

03781985.1 / 1 567 122

(73) Proprietor: Colgate-Palmolive Company New York, NY 10022 (US)

(72) Inventors: • Smith, Daniel, W. Belvidere, NJ 07823 (US) • Farooq, Amjad Hillsborough, NJ 08844 (US) • Wu, Donghui Bridgewater, NJ 08807 (US) • Heibel, Marija

Highland Park, NJ 08904 (US) • Drehs, Karen

Hillsborough, NJ 08844 (US)

(74) Representative: Daniels, Jeffrey Nicholas Page White & Farrer

Bedford House John Street

London WC1N 2BF (GB)

(56) References cited:

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5 10 15 20 25 30 35 40 45 50 55 Description TECHNICAL FIELD

[0001] The present invention relates to a class of compounds, and especially a group of fragrance precursor compounds which are used for creating a fragrance effect, preferably on surfaces such as fibers, skin, hair and hard surfaces. More specifically, the invention relates to a group of fragrance precursor compounds that break down on the above outlined surfaces, and as a result of this release perfume. In preferred embodiments the invention relates to certain hemiacetal and acetal compounds. Since the perfume or fragrance is only released when the compounds of the invention are broken down, the compounds of the invention are capable of providing a long-lasting fragrance effect. That is, the compounds of the present invention provide for a sustained release of fragrances.

[0002] In a further aspect, the present invention relates to a process for preparing these precursor compounds. Fra-grance precursor compounds consist of fraFra-grance raw materials and functional compounds such as surfactants, polymers etc., which provide benefits such as surface protection, surface conditioning, and/or surface cleaning.

[0003] In addition, the present invention relates to compositions comprising the compounds of the invention, and to fragrance raw material delivery systems which provide extended fragrance benefits.

BACKGROUND OF THE INVENTION

[0004] In WO-00/72816, fragrance delivery systems are described which comprise pro-fragrances or pro-accords selected from at least two of the following: (i) aldehyde and ketone releasing pro-fragrances, which pro-fragrances comprise inter alia and preferably oxazolidines; (ii) β-amino fragrances; and (iii) orthoester accords. The pro-fragrances described are capable of delivering fragrance raw material aldehydes and ketones to especially the human skin. More in detail, said international patent application is based on the finding that certain aldehyde fragrance raw materials, such as para-t-bucinal, cymal and lillial can be controllably released from particular heterocyclic pro-fragrances to especially the skin.

[0005] In laundry products, such as fabric softeners or detergents, generally perfume additives are present which make the said products more aesthetically pleasing to the consumers. The product should not only smell pleasantly and in that way add to the purchase perception, but also impart a pleasant and preferably long lasting fragrance to the fibers or fabrics treated therewith. One of the problems the person skilled in the art is confronted with is that the amount of perfume carryover is rather marginal; much fragrance is lost during washing and disappears down the drain. It would be very desirable to find ways of more effectively delivering perfume or fragrances to fibers, fabrics and textiles and to achieve the fragrance effect for a longer period of time.

[0006] Colgate-Palmolive application WO 02/057400 describes a water soluble cross-linked cationic polymer derived from the polymerisation of from 5 to 100 mole percent of a cationic vinyl addition monomer, from 0 to 95 mole percent of acrylamide, and from 70 to 300 ppm of a difunctional vinyl addition monomer cross-linking agent which enhances fragrance delivery from a fabric softening composition to the fabric to be softened.

[0007] In US Patent Application Publication No. 2003/0045447, there is described a fabric care composition comprising a cationic softening compound; a non-confined fragrance oil; and at least one fabric or skin beneficiating ingredient such as a fragrance oil, contained within pressure sensitive microcapsules to provide enhanced delivery of such beneficiating ingredient to the fabric.

[0008] International Patent Application Publication No. 98/27190 relates to dryer-activated fabric softening composi-tions comprising: (A) pro-perfume acetal compounds; (B) fabric softening compounds; and (C) optionally; (1) a carboxylic acid salt of a tertiary amine and/or a tertiary amine ester; and (2) a non-ionic softener; wherein, preferably, the Iodine Value of the total number of fatty acyl groups present in (A), (C)(1), and (C)(2) is from about 3 to about 60.

[0009] International Patent Application Publication No. 99/00347 relates to a fragrance delivery system for use in laundry detergent compositions including rinse-added and dryer-added fabric conditioning compositions which are in-tended to provide a long lasting "freshness" or "clean" scent to fabric.

OBJECTIVES OF THE PRESENT INVENTION

[0010] The first objective of the present invention is to provide alternative fragrances precursors or pro-fragrances. [0011] It is another objective to provide a more efficient delivery system of fragrance or perfume to surfaces. [0012] It is a further objective to provide functional fragrance precursor compounds that impart long lasting fragrance benefits, especially to fiber containing materials, such as fabrics and laundry.

[0013] Moreover, it is an objective of the present invention to provide a controlled or sustained release system releasing fragrance for a longer period of time.

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5 10 15 20 25 30 35 40 45 50 55 release of fragrance.

[0015] Other objectives will become apparent from reading the following description and are especially obtained for laundry products, personal care products, hard surface care products, oral products and so on.

SUMMARY OF THE INVENTION

[0016] According to the present invention a class of chemical compounds, and especially a class of fragrance precursor compounds has been found, which form the basis of products and methods which meet at least a number of the above-identified objectives.

[0017] More in particular, the present invention provides fragrance precursor compounds that are capable of breakdown under ambient conditions and that are the reaction product of a reaction between a hydroxyl compound, X-OH, and an aldehyde or a ketone. More in detail, the invention relates to a fragrance precursor compound according to claim 1. [0018] The present disclosure further provides fragrance precursor compounds comprising one or more of the com-pounds derived from the reaction of X-OH and an aldehyde or ketone, said fragrance precursor comcom-pounds being of the formula X-O-C(R) (R*) (OR**) wherein R is a C_6-24 alkyl group, a C_6-24 aralkyl group or a C_6-24 alkaryl group; R* is H or a C6-24 alkyl group, a C6-24 aralkyl group or a C6-24 alkaryl group; R** is H or X; X-O representing a moiety derived

from X-OH, and wherein X-OH is a compound selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, skin conditions, saccharides and polymers. [0019] In the fragrance precursors of the invention, X-OH is of structure IV:

wherein R1 and R2 are each independently, H or:

(a) C1-C22 alkylenecarboxy moiety having the formula: -(CH2)eR3 wherein R3 is -NHCOR4; or -OCOR4; or -NR5COR4;

and wherein R₄ and R₅ are each independently C₁-C₂₂ alkyl or alkenyl; and e is an integer from 1 to 22; or (b) C₁-C₂₂ linear or branched alkyl; or

(c) C1-C22 linear or branched alkenyl; or

(d) C2-C22 substituted or unsubstituted alkylenoxy; or

(e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C6-C22 substituted or unsubstituted aryloxy; or

(g) C7-C22 substituted or unsubstituted alkylenearyl; or

(h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyaryl; or (i) C₇-C₂₂ oxyalkylenearyl; or

(j) a unit having the formula: -(CH2)yR6

wherein R6 is -SO3M, -OSO3M, -PO3M, -OPO3M, Cl or mixtures thereof, wherein M is hydrogen, or one or more

salt forming cations sufficient to satisfy charge balance, or mixtures thereof; y is an integer from 1 to 22; and (k) a mixture comprising at least two of (a) through (j); and

q is an integer from 0 to 22; m is an integer from 0 to 22; Q is (CH2)or (CH2CHR7O) ; R7 is independently hydrogen,

methyl, ethyl, propyl or benzyl; and mixtures thereof; B is H or OH; Y is N; R₈ is H or C₁-C₄ alkyl; Z-_{is a counter}

anion, and preferably chloride,or methyl sulfate.

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5 10 15 20 25 30 35 40 45 50 55

wherein R₁ and R₂ are each independently, H or:

(a) C1-C22 alkylenecarboxy moiety having the formula- (CH2)eR3 wherein R3 is -NHCOR4; or -OCOR4; or -NR5COR4;

and wherein R4 and R5 are each independently C1-C22 akyl or alkenyl; and e is an integer from 1 to 22; or

(b) C₁-C₂₂ linear or branched alkyl; or (c) C1-C22 linear or branched alkenyl; or

(e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C₆-C₂₂ substituted or unsubstituted aryloxy; or

(h) C7-C22 substituted or unsubstituted alkyleneoxyary;or

(i) C7-C22 oxyalkylenearyl; or

(j) an anionic unit having the formula: - (CH2)yR6

wherein R₆ is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or more salt forming cations sufficient to satisfy charge balance, or mixtures thereof;

y is an integer from 1 to about 22; or

(k) a mixture comprising at least two of (a) through (j); and

q is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O) ; R₇ is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and Y is CR1 or N.

wherein R1 and R2, independently, represent C12 to C30 aliphatic hydrocarbon groups, R3 represents (CH2CH2O)pH,

CH₃ or H; T represents NH; n is an integer from 1 to 5; m is an integer from 1 to 5 and p is an integer from 1 to 10.

wherein R₁ is H or:

(a) C1-C22 alkylenecarboxy moiety having the formula:

- (CH₂)_eR₃ wherein R₃ is NHCOR₄; or -OCOR₄; or -NR₅COR₄; and wherein R₄ and R₅ are each independently C1-C22 akyl or alkenyl; and e is an integer from 1 to 22; or

(b) C₁-C₂₂ linear or branched alkyl; or (c) C1-C22 linear or branched alkenyl; or

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5 10 15 20 25 30 35 40 45 50 55

(d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C6-C22 substituted or unsubstituted aryloxy; or

(h) C₇-C₂₂ substituted or unsubstituted alkyleneoxyaryl; or (i) C7-C22 oxyalkylenearyl; or

(j) an anionic unit having the formula: -(CH2)yR6

wherein R₆ is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or more salt forming cations sufficient to satisfy charge balance, or mixtures thereof; y is an integer from 1 to about 22; and (k) a mixture comprising at least two of (a) through (j); and

q is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH2)m or CCH2CHR7O); R7 is

independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and Y is 0 or S.

wherein R1 and R2 are as defined in I; R’ and R" are each independently OH or R1 with the proviso that at least one of R’ and R" is OH.

[0021] In a second aspect, the present invention relates to a process for preparing the products of the invention, comprising reacting an aldehyde or ketone and a compound X-OH. X-OH is defined as above.

[0022] In a third aspect, the present invention relates to an aqueous composition for fragrance delivery comprising one or more of the reaction products according to the invention. Preferably, said composition of comprises a fabric softener.

BRIEF DESCRIPTION OF THE DRAWINGS [0023] In the drawings,

Figure 1 shows the reaction between a difatty amido amine and a C₁₀ aldehyde;

Figure 2 shows the release of fragrance from fabric treated with fabric softener containing the fragrance precursor compounds of the present invention after 1 and after 5 days, for a C8, C9 and C10 aldehydes by Solid Phase Micro

Extraction GC/MS;

Figure 3 shows a GC/MS spectrum of pure C₁₀ aldehyde, and the compound released from cloth treated with a fragrance precursor compound based on C10 aldehyde and Varisoft 510;

Figures 4a-4d show the proton-NMR spectra and the 13_{C-NMR spectra of Varisoft 510 and Varisoft 510 reacted}

with C10 aldehyde; and

Figures 5a-5c show the Mass Spectrum of the reaction products of Varisoft 510 with C10 aldehyde. DETAILED DESCRIPTION OF THE INVENTION

[0024] As mentioned herein-above, the present invention relates to the reaction product of a reaction between X-OH and an aldehyde or a ketone. In the aldehyde or ketone starting compounds of this reaction, the C_6-24 alkyl moiety encompasses linear and branched alkyl groups which can have one or more unsaturations. Such groups can be sub-stituted with substituents which do not adversely affect the fragrance activity of the aldehyde or ketones. Examples of such substituents encompass F, Cl and OH.

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5 10 15 20 25 30 35 40 45 50 55

the fragrance properties.

[0026] In a reference example, X-OH is of.the following structure:

(a) C1-C22 alkylenecarboxy moiety having the formula -(CH2)eR3 wherein R3 is -NHCOR4; or -OCOR4; or -NR5COR4;

and wherein R₄ and R₅ are each independently C₁-C₂₂ akyl or alkenyl; and e is an integer from 1 to 22; or (b) C1-C22 linear or branched alkyl; or

(c) C1-C22 linear or branched alkenyl; or

(d) C₂-C₂₂ substituted or unsubstituted alkylenoxy; or (e) C₃-C₂₂ substituted or unsubstituted alkylenoxy alkyl; or (f) C6-C22 substituted or unsubstituted aryloxy; or

(h) C7-C22 substituted or unsubstituted alkyleneoxyaryl; or

(i) C7-C22 oxyalkylenearyl; or

(j) an anionic unit having the formula: -(CH2)yR6

wherein R₆ is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or more salt forming cations sufficient to satisfy charge balance, or mixtures thereof; y is an integer from 1 to about 22; or (k) a mixture comprising at least two of (a) through (j); and q is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O); R₇ is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and Y is CR₁ or N.

[0027] The aldehydes useful in the present invention can be one or more of, but is not limited to the following group of aldehydes: (a) phenylacetaldehyde; or (b) p-methyl phenylacetaldehyde; or (c) p-isopropyl phenylacetaldehyde; or (d) methylnonyl acetaldehyde; or (e) phenylpropanal; or (f) 3-(4-t-butylphenyl)-2-methyl propanal; or (g) 3-(4-t-butylphenyl)-propanal; or (h) 3-(4-methoxyphenyl)-2-methylpropanal; or (i) 3-(4-isopropylphenyl)-2-methylpropanal; or (j) 3-(3,4-methylenedioxyphenyl)-2-methylpropanal; or (k) 3-(4-ethylphenyl)-2,2dimethylpropanal; or (l) phenylbutanal; or (m) 3-methyl-5-phenylpentanal; or (n) hexanal; or (o) trans-2-hexenal; or (p) cis-hex-3-enal; or (q) heptanal; or (r) cis-4-heptenal; or (s) 2-ethyl-2-heptenal; or (t) 2,6-dimethylpropanal; or (u) 2,4-heptadienal; or (v) octanal; or (w) 2-octenal; or (x) 3,7-dimethyloctanal; or (y) 3,7-dimethyl-2,6-octadien-1-al; or (z) 3,7-dimethyl-1,6-octadien-3-al; or

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5 10 15 20 25 30 35 40 45 50 55 (aa) 3,7-dimethyl-6-octenal; or (bb) 3,7-dimethyl-7-hydroxyoctan-1-al; or (cc) nonanal; or (dd) 6-nonenal; or (ee) 2,4-nonadienal; or (ff) 2,6-nonadienal; or (gg) decanal; or (hh) 2-methyl decanal; or (ii) 4-decenal; or (jj) 9-decenal; or (kk) 2,4-decadienal; or (ll) undecanal; or (mm) 2-methyldecanal; or (nn) 2-methylundecanal; or (oo) 2,6,10-trimethyl-9-undecenal; or (pp) undec-10-enyl aldehyde; or (qq) undec-8-enanal; or (rr) dodecanal; or (ss) tridecanal; or (tt) tetradecanal; or (uu) anisaldehyde; or (vv) bourgeonal; or (ww) cinnamic aldehyde; or (xx) α-amylcinnam-aldehyde; or (yy) α-hexyl cinnamaldehyde; or (zz) methoxy cinnamaldehyde; or (aaa) citronellal; or (bbb) hydroxy-citronellal; or (ccc) isocyclocitral; or (ddd) citronellyl oxyacet-aldehyde; or (eee) cortexaldehyde; or (fff) cumminic aldehyde ; or (ggg) cyclamen aldehyde; or (hhh) florhydral; or (iii) heliotropin; or (jjj) hydrotropic aldehyde; or (kkk) lilial; or (lll) vanillin; or (mmm) ethyl vanillin; or (nnn) benzaldehyde; or

(ooo) p-methyl benzaldehyde; or

(ppp) 3,4-dimethoxybenzaldehyde; or (qqq) 3-and4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxaldehyde; or

(rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde; or

(sss) 1-methyl-3-4-methylpentyl-3-cyclohexencarboxaldehyde; and (ttt) p-methylphenoxyacetaldehyde [0028] When an aldehyde is used the precursor of the invention is an acetal or hemiacetal.

[0029] The ketones useful in the present invention can be one or more of, but is not limited to the group of following ketones: (a) alpha-damascone; or (b) beta-damascone; or (c) delta-damascone; or (d) beta-damascenone; or (e) muscone; or (f) 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; or (g) cashmeran; or (h) cis-jasmone; or

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5 10 15 20 25 30 35 40 45 50 55 (i) dihydrojasmone; or (j) alpha-ionone; or (k) beta-ionone; or (l) dihydro-beta-ionone; or (m) gamma-methyl ionone; or (n) alpha-iso-methyl ionone; or (o) 4-(3,4-methylenedioxyphenyl)butan-2-one; or (p) 4-(4-hydroxyphenyl)butan-2-one; or

(q) methyl beta-naphthyl ketone; or (r) methyl cedryl ketone; or

(s) 6-acetyl-1,1,2,4,4,7-hexamethyltetralin (tonalid); or (t) 1-carvone; or (u) 5-cyclohexadecen-1-one; or (v) acetophenone; or (w) decatone; or (x) 2-[2-(4-methyl-3-cyclohexenyl-1-yl) propyl]cyclopentan-2-one; or (y) 2-sec-butylcyclohexanone; or (z) beta-dihydro ionone; or (aa) allyl ionone; or (bb) alpha-irone; or (cc) alpha-cetone; or (dd) alpha-irisone; or (ee) acetanisole; or (ff) geranyl acetone; or (gg) 1-(2-methl-s-isopropyl-2-cyclohexenyl)-1-propanone; or (hh) acetyl diisoamylene; or

(ii) methyl cyclocitrone; or (jj) 4-t-pentyl cyclohexanone; or (kk) p-t-butylcyclohexanone; or (ll) o-t-butylcyclohexanone; or (mm) ethyl amyl ketone; or (nn) ethyl pentyl ketone; or (oo) menthone; or

(pp) methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one; or (qq) fenchone; or

(rr) methyl naphthyl ketone; or (ss) propyl naphthy ketone; and (tt) methyl hydroxynaphthyl ketone

[0030] The fragrance precursor compounds of the invention were found to act as source for long lasting fragrance benefits, especially when applied to on surfaces such as fibers, skin, hair and hard surfaces, especially to fabrics and laundry. More specifically, the invention relates to fragrance precursor compounds that break down on surfaces such as fibers, skin, hair and hard surfaces, especially to fabrics and laundry, and as a result of this, release perfume. [0031] Since the perfume or fragrance is only released when the compounds of the invention are broken down, the compounds of the invention are capable of providing a long-lasting fragrance effect. That is, the compounds of the present invention provide for a sustained release of fragrances.

[0032] In accordance with the present invention there is a balance between the degree of breakdown of the fragrance precursor compounds to form the fragrance and the intensity of the fragrance. The intensity of the fragrance is substantially based on the fragrance formed..

[0033] To guarantee also the release of fragrance after a few days, such as after 5 and preferably after 7 days, the fragrance must be released by a controlled breakdown of the fragrance precursor compounds of the invention. That is, the equilibrium between the fragrance precursor compounds and the components including the fragrance must preferably be such that sufficient fragrance is released during a number of days. This equilibrium depends on the type of aldehyde and or ketone and the nature of compound X-OH.

[0034] In another reference example, the fragrance precursor compound is derived from a compound X-OH, selected from the group consisting of polyalkylene glycol, polyalkylene glycol ester and polysaccharide. Preferably, the poly-alkylene glycol or the ester thereof are based on polyethylene glycol, polypropylene glycol and poly(ethylene/propylene) glycol.

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[0035] The fragrance precursor compounds of the present invention are especially aimed to be incorporated in com-positions to treat surfaces such as fibers, skin, hair and hard surfaces, especially to fabrics and laundry. From that perspective, it would be highly desirable to have available compounds which not only are compatible with compositions used to treat such materials, but additionally would have properties useful in such compositions. The present disclosure also relates to fragrance precursor compounds of the type described herein-above, wherein X-OH is a surfactant de-scribed herein-above as I. The preferred structure is of the formula (R1-(CH2)z)x-N-(CH2)y-OH, wherein R1, independently,

is selected from the group consisting of a fatty amido amine moiety of the formula AlkC(O)NH-, a moiety having the formula AlkC(O)O, a moiety having the formula Alk-O-, wherein Alk is a linear or branched C₂-C₂₄ alkyl or alkylene group, optionally substituted with one or more hydroxyl groups, nitro groups, amine groups, and/or halogen atoms, or represents a CHOH-R group. z and y, independently, are integers having a value between 0 and 10, preferably between 0 and 5, more preferably between 1 and 3; x represents 2 or 3.

[0036] These fragrance precursor compounds are for instance based on fatty or di fatty amido amines, which in themselves have fabric softening properties. Examples of such fatty amido amines are for instance the fabric softeners sold under the trade name Varisoft, such as Varisoft 510 (ex Goldschmidt, Germany) as mentioned in US-A-5,501,806. As will follow from the examples herein-below the reaction product between a di fatty amido amine (Varisoft 510) and C8-12 aldehydes give pro-fragrances that give continuous release of the aldehydes until after more than 1 week.

[0037] The fragrance precursor compounds of the invention can be obtained by reacting an aldehyde and or ketone fragrance and a compound X-OH of structure IV. This forms a further aspect of the present invention.

[0038] In fact, the formation of a acetal, hemiacetal, and or a ketal involves a compound comprising at least one nucleophilic free -OH group and an aldehyde and or ketone. This reaction is known per se. Preferably, this reaction is carried out in an aqueous solution in the presence of an acid or a catalyst.

[0039] In figure 1, the reaction between an amido amine and a C10 aldehyde is shown as an example. An example of

the amido amine starting compound is Varisoft 510. The products obtained from this reaction can very suitably be incorporated in a product formula such as a rinse cycle fabric softener, and from said formula be delivered to a surface to give a long lasting fragrance.

[0040] Dependent on the number of free hydroxyl groups, one or more aldehyde and or ketone molecules can be coupled to the XOH molecule. This makes that the capacity of fragrance to be released can be controlled to some degree. [0041] In yet a further aspect, the present invention relates to an aqueous composition for fragrance delivery comprising one or more fragrance precursor compounds according to the invention. Preferable said aqueous composition is a fabric softener composition and especially a rinse cycle fabric softener composition.

[0042] Good results are obtained when incorporating between 0.001-10 wt.% of fragrance precursor of the invention, drawn to the total weight of the composition, in the aqueous composition. Preferably between 0.01 and 35 wt.% and more preferably between 2 and 15 wt.% of any fabric softening active ingredient is present. A preferred cationic softener is an esterquat softener having the following structural formula:

wherein R4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms, R2 and R3 represent (CH2)9-R5

where R5 represents an alkoxy carbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, (C1-C4)-alkyl

substituted phenyl, OH or H; q, s, and t, each independently, represent an integer from 1 to 3; and X-_{is a softener}

compatible anion.

[0043] A fragrance precursor compound delivery system is also provided, which comprises: (a) at least about 0.001% by weight, of a fragrance precursor conjugate, comprising:

(i) a fragrance precursor compound as described herein capable of releasing a fragrance raw material; or (ii) a fragrance raw material; and

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(b) the balance carriers and adjunct ingredients.

[0044] A laundry detergent is also provided, which comprises:

(a) at least about 0.001% by weight, of a fragrance precursor conjugate, comprising:

(b) effective amount of a detersive surfactant; and (c) the balance carriers and adjunct ingredients.

[0045] The fabric softener or fabric softening dryer sheet is also provided, which comprises: a) at least about 0.001% by weight, of a fragrance precursor conjugate, comprising:

(b) effective amount of a fabric softening compound; and (c) the balance carriers and adjunct ingredients.

[0046] The perfume or fine fragrance is also provided, which comprises:

a) at least about 0.001% by weight, of a fragrance precursor conjugate, comprising:

(c) at least about 0.01% to about 99% by weight, of an admixture of fragrance raw materials; and (d) the balance carriers and adjunct ingredients.

[0047] A personal care product, or oral care product or hard surface care product is also provided, which comprises: (a) from about 0.001% by weight, of a fragrance precursor conjugate, comprising:

(b) from about 0.1% by weight, of a surfactant, or emollient or abrasive or anti-bacterial agent suitable for use in personal care or oral care or hard surface care products; and

(c) the balance carriers and adjunct ingredients.

[0048] The balance carriers and adjunct ingredients are typically selected from:

builders, optical brighteners, bleaches, bleach boosters, bleach catalysts, bleach activators, soil release polymers, dye fluorescers, fabric conditioners, hydrolyzable surfactants, transfer agents, dispersents, enzymes, suds sup-pressers, dyes, perfumes, colorants, filler salts, hydrotropes, hotoactivators,preservatives, anti-oxidants, chelants, stabilizers, anti-shrinkage agents, anti-wrinkle agents, germicides, fungicides, anti corrosion agents, and mixtures thereof.

[0049] The invention will be described in more detail in the following examples, which do not limit the invention, but merely illustrate the invention. Unless otherwise indicated, all percentages are by weight drawn to the weight of the final composition.

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5 10 15 20 25 30 35 40 45 50 55 Reference Example 1

[0050] Fragrance precursors can be formed by preferable but not limited to combining Varisoft 510 (3.0g) with decyl aldehyde (1.8ml), water (0.2ml) and p-toluenesulfonic acid monohydrate (20mg). The reaction was then heated in a 60°C. oil bath with stirring overnight open to the air. The reaction was then cooled to room temperature and solidified upon standing. In figure 4, the proton- and 13_{C-NMR spectra are given of Varisoft 510 and of Varisoft 510 reacted with}

C₁₀ aldehyde. Figure 5 shows the mass spectrum of the reaction products.

[0051] Fragrance precursors can also be formed by preferable but not limited to the above reaction without the addition of water.

Reference Example 2

[0052] Fabric softener compositions are prepared comprising 5 wt.% esterquat having the following structural formula:

wherein R4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms, R2 and R3 represent (CH₂)_s-R₅ where R5 represents an alkoxy carbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, (C1-C4)-alkyl

substituted phenyl, OH or H; q, s, and t, each independently, represent an integer from 1 to 3; and X-_{is a softener}

compatible anion. 1 wt.% of the amido amine fragrance precursor compounds prepared; and 94 wt.% water. Fabric was treated with the fabric softener composition prepared, and the release of fragrance was measured after 1 day and after 5 days by solid phase micro extraction (SPME) coupled with GC/MS. For C10 aldehydes the amount of fragrance released

on day 1 and on day 5 is about the same, showing the desired sustained release of fragrance from the fabric surface.

Claims

1. A fragrance precursor compound comprising one or more of the compounds derived from the reaction of X-OH and an aldehyde or ketone, said fragrance precursor compounds being of the formula X-O-C(R)(R*)(OR**) wherein R is a C_6-24 alkyl group, a C_6-24 aralkyl group or a C_6-24 alkaryl group; R* is H or a C_6-24 alkyl group, a C_6-24 aralkyl group or a C6-24 alkaryl group; optionally wherein the C6-24 alkyl groups, C6-24 aralkyl groups and/or C6-24 alkaryl

groups are branched and/or comprise unsaturations or substituents which do not adversely affect the fragrance activity of the aldehyde or ketone; R** is H or X; X-O representing a moiety derived from X-OH, wherein X-OH comprises at least one nucleophilic free -OH group and is capable of forming an acetal, hemiacetal and/or a ketal with the aldehyde or ketone, and wherein X-OH is a compound selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, skin condi-tioners, saccharides and polymers, wherein X-OH is of the following structure:

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5 10 15 20 25 30 35 40 45 50 55

(a) C1-C22 alkylenecarboxy moiety having the formula: -(CH2)eR3 wherein R3 is -NHCOR4; or -OCOR4; or

-NR5COR4; and wherein R4 and R5 are each independently C1-C22 alkyl or alkenyl; and e is an integer from 1

to 22; or

(b) C1-C22 linear or branched alkyl; or

(c) C₁-C₂₂ linear or branched alkenyl; or

(e) C3-C22 substituted or unsubstituted alkylenoxy alkyl; or

(f) C₆-C₂₂ substituted or unsubstituted aryloxy; or (g) C₇-C₂₂ substituted or unsubstituted alkylenearyl; or (h) C7-C22 substituted or unsubstituted alkyleneoxyaryl; or

(i) C₇-C₂₂ oxyalkylenearyl; or (j) a unit having the formula:

-(CH₂)_yR₆

wherein R₆ is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or mixtures thereof, wherein M is hydrogen, or one or more salt forming cations sufficient to satisfy charge balance, or mixtures thereof; y is an integer from 1 to 22; and (k) a mixture comprising at least two of (a) through (j); and

q is an integer from 0 to 22; m is an integer from 0 to 22; Q is (CH2) or (CH2CHR7O); R7 is independently

hydrogen, methyl, ethyl, propyl or benzyl; and mixtures thereof; B is H or OH; Y is N; R8 is H or C1-C4 alkyl; Z

-is a counter anion, and preferably chloride, or methyl sulfate.

2. The fragrance precursor of claim 1, wherein the aldehyde is at least one aldehyde chosen from: (a) phenylacetaldehyde; or (b) p-methyl phenylacetaldehyde; or (c) p-isopropyl phenylacetaldehyde; or (d) methylnonyl acetaldehyde; or (e) phenylpropanal; or (f) 3-(4-t-butylphenyl)-2-methyl propanal; or (g) 3-(4-t-butylphenyl)-propanal; or (h) 3-(4-methoxyphenyl)-2-methylpropanal; or (i) 3-(4-isopropylphenyl)-2-methylpropanal; or (j) 3-(3,4-methylenedioxyphenyl)-2-methylpropanal; or (k) 3-(4-ethylphenyl)-2,2dimethylpropanal; or (l) phenylbutanal; or (m) 3-methyl-5-phenylpentanal; or (n) hexanal; or (o) trans-2-hexenal; or (p) cis-hex-3-enal; or (q) heptanal; or (r) cis-4-heptenal; or

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5 10 15 20 25 30 35 40 45 50 55 (s) 2-ethyl-2-heptenal; or (t) 2,6-dimethylpropanal; or (u) 2,4-heptadienal; or (v) octanal; or (w) 2-octenal; or (x) 3,7-dimethyloctanal; or (y) 3,7-dimethyl-2,6-octadien-1-al; or (z) 3,7-dimethyl-1,6-octadien-3-al; or (aa) 3,7-dimethyl-6-octenal; or (bb) 3,7-dimethyl-7-hydroxyoctan-1-al; or (cc) nonanal; or (dd) 6-nonenal; or (ee) 2,4-nonadienal; or (ff) 2,6-nonadienal; or (gg) decanal; or (hh) 2-methyl decanal; or (ii) 4-decenal; or (jj) 9-decenal; or (kk) 2,4-decadienal; or (ll) undecanal; or (mm)2-methyldecanal; or (nn) 2-methylundecanal; or (oo) 2,6,10-trimethyl-9-undecenal; or (pp) undec-10-enyl aldehyde; or (qq) undec-8-enanal; or (rr) dodecanal; or (ss) tridecanal; or (tt) tetradecanal; or (uu) anisaldehyde; or (w) bourgeonal; or (ww) cinnamic aldehyde; or (xx) α-amylcinnam-aldehyde; or (yy) α-hexyl cinnamaldehyde; or (zz) methoxy cinnamaldehyde; or (aaa) citronellal; or (bbb)hydroxy-citronellal; or (ccc) isocyclocitral; or (ddd) citronellyl oxyacet-aldehyde; or (eee) cortexaldehyde; or (fff) cumminic aldehyde; or (ggg) cyclamen aldehyde;or (hhh) florhydral; or (iii) heliotropin; or (jjj) hydrotropic aldehyde; or (kkk)lilial; or (lll) vanillin; or (mmm) ethyl vanillin; or (nnn) benzaldehyde; or

(ooo) p-methyl benzaldehyde; or (ppp) 3,4-dimethoxybenzaldehyde; or

(qqq) 3-and4-(4-hydroxy-4-methyl-pentyl-3-cyclohexene-1-carboxaldehyde; or (rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde; or

(sss) 1-methyl-3-4-methylpentyl-3-cyclohexencarboxaldehyde; or (ttt) p-methylphenoxyacetaldehyde.

3. The fragrance precursor of claim 1, wherein the ketone is at least one ketone chosen from: (a) alpha-damascone; or

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5 10 15 20 25 30 35 40 45 50 55 (b) beta-damascone; or (c) delta-damascone; or (d) beta-damascenone; or (e) muscone; or (f) 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; or (g) cashmeran; or (h) cis-jasmone; or (i) dihydrojasmone; or (j) alpha-ionone; or (k) beta-ionone; or (l) dihydro-beta-ionone; or (m) gamma-methyl ionone; or (n) alpha-iso-methyl ionone; or (o) 4-(3,4-methylenedioxyphenyl)butan-2-one; or (p) 4-(4-hydroxyphenyl)butan-2-one; or

(q) methyl beta-naphthyl ketone; or (r) methyl cedryl ketone; or

(s) 6-acetyl-1,1,2,4,4,7-hexamethyltetralin (tonalid) ; or (t) 1-carvone; or (u) 5-cyclohexadecen-1-one; or (v) acetophenone; or (w) decatone; or (x) 2-[2-(4-methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-one; or (y) 2-sec-butylcyclohexanone; or (z) beta-dihydro ionone; or (aa) allyl ionone; or (bb) alpha-irone; or (cc) alpha-cetone; or (dd) alpha-irisone; or (ee) acetanisole; or (ff) geranyl acetone; or (gg) 1-(2-methyl-5-isopropyl-2-cyclohexenyl)-1-propanone; or (hh) acetyl diisoamylene; or

(ii) methyl cyclocitrone; or (jj) 4-t-pentyl cyclohexanone; or (kk) p-t-butylcyclohexanone; or (ll) o-t-butylcyclohexanone; or (mm) ethyl amyl ketone; or (nn) ethyl pentyl ketone; or (oo) menthone; or

(pp) methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one; or (qq) fenchone; or

(rr) methyl naphthyl ketone; or (ss) propyl naphthy ketone; and (tt) methyl hydroxynaphthyl ketone.

4. A fragrance precursor compound delivery system comprising:

(a) at least 0.001 % by weight of the fragrance precursor compound of claim 1 capable of releasing a fragrance raw material; and

(b) the balance carriers and adjunct ingredients. 5. A laundry detergent comprising:

(a) at least 0.001 % by weight of the fragrance precursor compound of claim 1 capable of releasing a fragrance raw material;

(b) an effective amount of a detersive surfactant; and (c) the balance carriers and adjunct ingredients.

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5 10 15 20 25 30 35 40 45 50 55

6. A fabric softener or fabric softening dryer sheet comprising:

(a) at least 0.001% by weight of the fragrance precursor compound of claim 1 capable of releasing a fragrance raw material;

(b) an effective amount of a fabric softening compound; and (c) the balance carriers and adjunct ingredients.

7. A perfume or fine fragrance comprising;

(a) at least 0.001% by weight of the fragrance precursor compound of claim 1 capable of releasing a fragrance raw material;

(b) at least 0.01% to 99% by weight of an admixture of fragrance raw materials; and (c) the balance carriers and adjunct ingredients.

8. A personal care product, or oral care product or hard surface care product comprising:

(a) from 0.001% by weight of the fragrance precursor compound of claim 1 capable of releasing a fragrance raw material;

(b) from 0.1 % by weight, of a surfactant, or emollient or abrasive or anti-bacterial agent suitable for use in personal care or oral care or hard surface care products; and

(c) the balance carriers and adjunct ingredients.

9. A method of preparing the fragrance precursor compound of claim 1 comprising reacting the aldehyde or ketone and X-OH.

10. The method of claim 9, wherein the reaction is acid catalyzed.

Patentansprüche

1. Duftstoffvorläuferverbindung, die eine oder mehrere der Verbindungen umfasst, die aus der Reaktion von X-OH und einem Aldehyd oder Keton abgeleitet ist, wobei die Duftstoffvorläuferverbindungen die Formel X-O-C(R)(R*)(OR**) haben, wobei R eine C6-24-Alkylgruppe, eine C6-24-Aralkylgruppe oder eine C6-24-Alkarylgruppe ist;

R* H oder eine C6-24-Alkylgruppe, eine C6-24-Aralkylgruppe oder eine C6-24-Alkarylgruppe ist; gegebenenfalls wobei

die C_6-24-Alkylgruppen, die C_6-24-Aralkylgruppen und/oder die C_6-24-Alkarylgruppen verzweigt sind und/oder Unge-sättigtheiten oder Substituenten umfassen, die die Duftstoffaktivität des Aldehyds oder Ketons nicht beeinträchtigen; R** H oder X ist; X-O für eine Moleküleinheit steht, die von X-OH abgeleitet ist, wobei X-OH mindestens eine nukleophile freie -OH-Gruppe umfasst und ein Acetal, Hemiacetal und/oder ein Ketal mit dem Aldehyd oder Keton bilden kann und wobei X-OH eine Verbindung ist, die aus der Gruppe bestehend aus Tensiden, Weichspülern, Weichmachervorläufer-Esteraminen, Weichmachervorläufer-Amidoaminen, Haarspülungen, Hautkonditionie-rungsmitteln, Sacchariden und Polymeren ausgewählt ist, wobei X-OH die folgende Struktur hat:

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wobei R₁ und R₂ jeweils unabhängig H oder Folgendes sind: (a) eine C1-C22-Alkylencarboxy-Moleküleinheit mit der Formel:

- (CH₂) _eR₃, wobei R₃ -NHCOR₄ oder -OCOR₄ oder -NR₅COR₄ ist und wobei R₄ und R₅ jeweils unabhängig C1-C22-Alkyl oder-Alkenyl sind und e eine ganze Zahl von 1 bis 22 ist; oder

(b) lineares oder verzweigtes C₁-C₂₂-Alkyl oder (c) lineares oder verzweigtes C1-C22-Alkenyl oder

(d) substituiertes oder unsubstituiertes C2-C22-Alkylenoxy oder

(e) substituiertes oder unsubstituiertes C₃-C₂₂-Alkylenoxyalkyl oder (f) substituiertes oder unsubstituiertes C₆-C₂₂-Aryloxy oder

(g) substituiertes oder unsubstituiertes C7-C22-Alkylenaryl oder

(h) substituiertes oder unsubstituiertes C7-C22-Alkylenoxyaryl oder

(i) C₇-C₂₂-Oxyalkylenaryl oder (j) eine Einheit mit der Formel: - (CH₂)_yR₆,

wobei R6 -SO3M, -OSO3M, -PO3M, -OPO3M, Cl oder Gemische davon ist, wobei M Wasserstoff oder ein oder

mehrere salzbildende Kationen, die dazu ausreichen, dem Ladungsausgleich zu genügen, oder Gemische davon ist; y eine ganze Zahl von 1 bis 22 ist; und

(k) ein Gemisch, das mindestens zwei von (a) bis (j) umfasst; und

q eine ganze Zahl von 0 bis 22 ist; m eine ganze Zahl von 0 bis 22 ist; Q (CH₂) oder (CH₂CHR₇OH) ist; R₇ unabhängig Wasserstoff, Methyl, Ethyl, Propyl oder Benzyl und Gemische davon ist; B H oder OH ist; Y N ist; R8 H oder C1-C4-Alkyl ist; Z- ein Gegenanion und vorzugsweise Chlorid oder Methylsulfat ist.

2. Duftstoffvorläufer nach Anspruch 1, wobei der Aldehyd mindestens ein Aldehyd ist, der aus den folgenden ausgewählt ist:

(a) Phenylacetaldehyd oder (b) p-Methylphenylacetaldehyd oder (c) p-Isopropylphenylacetaldehyd oder (d) Methylnonylacetaldehyd oder (e) Phenylpropanal oder

(f) 3-(4-t-Butylphenyl)-2-methylpropanal oder (g) 3-(4-t-Butylphenyl)propanal oder

(h) 3-(4-Methoxyphenyl)-2-methylpropanal oder (i) 3-(4-Isopropylphenyl)-2-methylpropanal oder (j) 3-(3,4-Methylendioxyphenyl)-2-methylpropanal oder (k) 3-(4-Ethylphenyl)-2,2-dimethylpropanal oder (1) Phenylbutanal oder

(m) 3-Methyl-5-phenylpentanal oder (n) Hexanal oder

(o) trans-2-Hexenal oder (p) cis-Hex-3-enal oder (q) Heptanal oder (r) cis-4-Heptenal oder (s) 2-Ethyl-2-heptenal oder (t) 2,6-Dimethylpropanal oder (u) 2,4-Heptadienal oder (v) Octanal oder (w) 2-Octenal oder

(x) 3,7-Dimethyloctanal oder

(y) 3,7-Dimethyl-2,6-octadien-1-al oder (z) 3,7-Dimethyl-1,6-octadien-3-al oder (aa) 3,7-Dimethyl-6-octenal oder

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5 10 15 20 25 30 35 40 45 50 55 (cc) Nonanal oder (dd) 6-Nonenal oder (ee) 2,4-Nonadienal oder (ff) 2,6-Nonadienal oder (gg) Decanal oder (hh) 2-Methyldecanal oder (ii) 4-Decenal oder (jj) 9-Decenal oder (kk) 2,4-Decadienal oder (11) Undecanal oder (mm) 2-Methyldecanal oder (nn) 2-Methylundecanal oder

(oo) 2,6,10-Trimethyl-9-undecenal oder (pp) Undec-10-enylaldehyd oder (qq) Undec-8-enanal oder (rr) Dodecanal oder (ss) Tridecanal oder (tt) Tetradecanal oder (uu) Anisaldehyd oder (vv) Bourgeonal oder (ww) Zimtaldehyd oder

(xx) α-Amylcinnamaldehyd oder (yy) α-Hexylcinnamaldehyd oder (zz) Methoxycinnamaldehyd oder (aaa) Citronellal oder

(bbb) Hydroxycitronellal oder (ccc) Isocyclocitral oder

(ddd) Citronellyloxyacetaldehyd oder (eee) Cortexaldehyd oder

(fff) Cuminaldehyd oder (ggg) Cyclamenaldehyd oder (hhh) Florhydral oder (iii) Heliotropin oder (jjj) Hydrotropaldehyd oder (kkk) Lilial oder

(111) Vanillin oder (mmm) Ethylvanillin oder (nnn) Benzaldehyd oder (ooo) p-Methylbenzaldehyd oder (ppp) 3,4-Dimethoxybenzaldehyd oder

(qqq) 3- und 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexen-1-carboxaldehyd oder (rrr) 2,4-Dimethyl-3-cyclohexen-1-carboxaldehyd oder

(sss) 1-Methyl-3,4-methylpentyl-3-cyclohexencarboxaldehyd oder (ttt) p-Methylphenoxyacetaldehyd.

3. Duftstoffvorläufer nach Anspruch 1, wobei das Keton mindestens ein Keton ist, das aus den folgenden ausgewählt ist: (a) alpha-Damascon oder

(b) beta-Damascon oder (c) delta-Damascon oder (d) beta-Damascenon oder (e) Muscon oder

(f) 6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanon oder

(g) Cashmeran oder (h) cis-Jasmon oder (i) Dihydrojasmon oder (j) alpha-Ionon oder

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5 10 15 20 25 30 35 40 45 50 55 (k) beta-Ionon oder (1) Dihydro-beta-ionon oder (m) gamma-Methylionon oder (n) alpha-Isomethylionon oder

(o) 4-(3,4-Methylendioxyphenyl)butan-2-on oder (p) 4-(4-Hydroxyphenyl)butan-2-on oder (q) Methyl-beta-naphthylketon oder (r) Methylcedrylketon oder (s) 6-Acetyl-1,1,2,4,4,7-hexamethyltetralin (Tonalid) oder (t) 1-Carvon oder

(u) 5-Cyclohexadecen-1-on oder (v) Acetophenon oder

(w) Decaton oder

(x) 2-[2-(4-Methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-on oder (y) 2-sek.-Butylcyclohexanon oder

(z) beta-Dihydroionon oder (aa) Allylionon oder (bb) alpha-Iron oder (cc) alpha-Ceton oder (dd) alpha-Irison oder (ee) Acetanisol oder (ff) Geranylaceton oder

(gg) 1-(2-Methyl-5-isopropyl-2-cyclohexenyl)-1-propanon oder (hh) Acetyldiisoamylen oder

(ii) Methylcyclocitron oder (jj) 4-t-Pentylcyclohexanon oder (kk) p-t-Butylcyclohexanon oder (11) o-t-Butylcyclohexanon oder (mm) Ethylamylketon oder (nn) Ethylpentylketon oder (oo) Menthon oder

(pp) Methyl-7,3-dihydro-2H-1,5-benzodioxepin-3-on oder (qq) Fenchon oder (rr) Methylnaphthylketon oder

(ss) Propylnaphthylketon oder (tt) Methylhydroxynaphthylketon.

4. Duftstoffvorläuferverbindungsabgabesystem, das Folgendes umfasst:

(a) mindestens 0,001 Gew.-% der Duftstoffvorläuferverbindung nach Anspruch 1, die einen Duftstoffrohstoff freisetzen kann; und

(b) als Rest Trägerstoffe und Zusatzbestandteile. 5. Waschmittel, das Folgendes umfasst:

(a) mindestens 0,001 Gew.-% der Duftstoffvorläuferverbindung nach Anspruch 1, die einen Duftstoffrohstoff freisetzen kann;

(b) eine wirksame Menge eines reinigenden Tensids und (c) als Rest Trägerstoffe und Zusatzbestandteile.

6. Weichspüler oder weichspülendes Trocknertuch, der bzw. das Folgendes umfasst:

(b) eine wirksame Menge einer weichspülenden Verbindung und (c) als Rest Trägerstoffe und Zusatzbestandteile.

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(b) mindestens 0,01 Gew.-% bis 99 Gew.-% eines Gemischs von Duftstoffrohstoffen und (c) als Rest Trägerstoffe und Zusatzbestandteile.

8. Körperpflegeprodukt oder Mundpflegeprodukt oder Produkt zur Pflege harter Oberflächen, das Folgendes umfasst: (a) von 0,001 Gew.-% der Duftstoffvorläuferverbindung nach Anspruch 1, die einen Duftstoffrohstoff freisetzen kann;

(b) von 0,1 Gew.-% eines Tensids oder Weichmachers oder Schleifmittels oder antibakteriellen Mittels, das bzw. der zur Verwendung in Körperpflege- oder Mundpflegeprodukten oder Produkten zur Pflege harter Ober-flächen geeignet ist; und

(c) als Rest Trägerstoffe und Zusatzbestandteile.

9. Verfahren zur Herstellung der Duftstoffvorläuferverbindung nach Anspruch 1, das das Umsetzen des Aldehyds oder Ketons und von X-OH umfasst.

10. Verfahren nach Anspruch 9, wobei die Reaktion säurekatalysiert ist.

Revendications

1. Un composé précurseur de parfum comprenant un ou des composés dérivés de la réaction de X-OH et d’un aldéhyde ou d’une cétone, lesdits composés précurseurs de parfums étant de formule X-O-C(R)(R*)(OR**) dans laquelle R est un groupe alkyle C_6-24, un groupe aralkyle C_6-24 ou un groupe alkaryle C_6-24; R* est H ou un groupe alkyle C6-24, un groupe aralkyle C6-24 ou un groupe alkaryle C6-24; en option dans laquelle les groupes alkyles C6-24, les

groupes aralkyles C6-24 et/ou les groupes alkaryles C6-24 sont ramifiés et/ou comprennent des insaturations ou des

substituants qui n’ont pas d’effet négatif sur l’activité de parfum de l’aldéhyde ou de la cétone ; R** est H ou X ; X-O représentant une fraction dérivée de X-X-OH, dans laquelle X-X-OH comprend au moins un groupe -X-OH nucléophile libre et est capable de former un acétal, un hémiacétal et/ou un cétal avec l’aldéhyde ou la cétone, et dans laquelle X-OH est un composé sélectionné dans le groupe constitué par des tensioactifs, des adoucissants pour textile, des ester amines précurseurs d’adoucissants, des amido amines précurseurs d’adoucissants, des après-shampooings, des revitalisants de la peau, des saccharides et des polymères, dans lequel X-OH est de la structure suivante :

dans laquelle R1 et R2 sont, chacun indépendamment, H ou :

(a) une fraction d’alkylènecarboxy C₁-C₂₂ ayant la formule :

- (CH2)eR3 dans laquelle R3 est -NHCOR4; ou -OCOR4; ou -NR5COR4; et dans laquelle R4 et R5 sont

chacun indépendamment un alkyle ou un alkényle C1-C22; et e est un entier compris entre 1 et 22 ; ou

(b) un alkyle C1-C22 linéaire ou ramifié ; ou

(c) un alkényle C₁-C₂₂ linéaire ou ramifié ; ou

(d) un alkylènoxy C2-C22 substitué ou non substitué ; ou

(e) un alkylènoxy alkyl C3-C22 substitué ou non substitué ; ou

(f) un aryloxy C₆-C₂₂ substitué ou non substitué ; ou (g) un alkylènearyl C₇-C₂₂ substitué ou non substitué ; ou (h) un alkylèneoxyaryl C7-C22 substitué ou non substitué ; ou

(i) un oxyalkylènearyl C₇-C₂₂; ou (j) une unité ayant la formule :

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5 10 15 20 25 30 35 40 45 50 55 -(CH2)yR6

dans laquelle R6 est -SO3M, -OSO3M, -PO3M, -OPO3M, Cl ou des mélanges de ceux-ci, dans laquelle M est

un hydrogène ou un ou plusieurs cations formant suffisamment de sel pour satisfaire à l’équilibre des charges, ou des mélanges de ceux-ci ; y est un entier compris entre 1 et 22 ; et

(k) un mélange comprenant au moins deux compris entre (a) et (j) ; et

q est un entier compris entre 0 et 22 ; m est un entier compris entre 0 et 22 ; Q est (CH₂) ou (CH₂CHR₇O) ; R₇ est indépendamment l’hydrogène, le méthyle, l’éthyle, le propyle ou le benzyle ; et des mélanges de ceux-ci ; B est H ou OH ; et Y est N ; R8 est H ou l’alkyle C1-C4; Z- est un contre-anion et, de préférence, un chlorure

ou un sulfate de méthyle.

2. Le précurseur de parfum selon la revendication 1, dans laquelle l’aldéhyde est au moins un aldéhyde choisi parmi : (a) le phénylacétaldéhyde ; ou (b) le p-méthyl phénylacétaldéhyde ; ou (c) le p-isopropyl phénylacétaldéhyde ; ou (d) le méthylnonyl acétaldéhyde ; ou (e) le phénylpropanal ; ou (f) le 3-(4-t-butylphényl)-2-méthyl propanal ; ou (g) le 3-(4-t-butylphényl)-propanal ; ou (h) le 3-(4-méthoxyphényl)-2-méthylpropanal ; ou (i) le 3-(4-isopropylphényl)-2-méthylpropanal ; ou (j) le 3-(3,4-méthylènedioxyphényl)-2-méthylpropanal ; ou (k) le 3-(4-éthylphényl)-2,2-diméthylpropanal ; ou (I) le phénylbutanal ; ou (m) le 3-méthyl-5-phénylpentanal ; ou (n) l’hexanal ; ou (o) le trans-2-hexénal ; ou (p) le cis-hex-3-énal ; ou (q) l’heptanal ; ou (r) le cis-4-hepténal ; ou (s) le 2-éthyl-2-hepténal ; ou (t) le 2,6-diméthylpropanal ; ou (u) le 2,4-heptadiénal ; ou (v) l’octanal ; ou (w) le 2-octénal ; ou (x) le 3,7-diméthyloctanal ; ou (y) le 3,7-diméthyl-2,6-octadién-1-al ; ou (z) le 3,7-diméthyl-1,6-octadién-3-al ; ou (aa) le 3,7-diméthyl-6-octénal ; ou (bb) le 3,7-diméthyl-7-hydroxyoctan-1-al ; ou (cc) le nonanal ; ou (dd) le 6-nonénal ; ou (ee) le 2,4-nonadiénal ; ou (ff) le 2,6-nonadiénal ; ou (gg) le décanal ; ou (hh) le 2-méthyl décanal ; ou (ii) le 4-décénal ; ou (jj) le 9-décénal ; ou (kk) le 2,4-décadiénal ; ou (II) l’undécanal ; ou (mm) le 2-méthyldécanal ; ou (nn) le 2-méthylundécanal ; ou (oo) le 2,6,10-triméthyl-9-undécénal ; ou (pp) l’aldéhyde d"undéc-10-ényle ; ou (qq) l’undéc-8-énanal ; ou (rr) le dodécanal ; ou

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5 10 15 20 25 30 35 40 45 50 55 (ss) le tridécanal ; ou (tt) le tétradécanal ; ou (uu) l’anisaldéhyde ; ou (w) le bourgeonal ; ou (ww) l’aldéhyde cinnamique ; ou (xx) le α-amylcinnamaldéhyde ; ou (yy) le α-hexyl cinnamaldéhyde ; ou (zz) le méthoxy cinnamaldéhyde ; ou (aaa) le citronellal ; ou (bbb) l’hydroxy-citronellal ; ou (ccc) l’isocyclocitral ; ou (ddd) le citronellyl oxyacétaldéhyde ; ou (eee) le cortexaldéhyde ; ou (fff) l’aldéhyde cumminique ; ou (ggg) l’aldéhyde de cyclamen ; ou (hhh) le florhydral ; ou (iii) l’héliotropine ; ou (jjj) l’aldéhyde hydrotropique ; ou (kkk) le lilial ; ou (III) la vanilline ; ou (mmm) l’éthylvanilline ; ou (nnn) le benzaldéhyde ; ou

(ooo) le p-méthyl benzaldéhyde ; ou (ppp) le 3,4-diméthoxybenzaldéhyde ; ou

(qqq) le 3- et 4-(4-hydroxy-4-méthyl-pentyl)-3-cyclohexène-1-carboxaldéhyde ; ou (rrr) le 2,4-diméthyl-3-cyclohexène-1-carboxaldéhyde ; ou

(sss) le 1-méthyl-3-4-méthylpentyl-3-cyclohexèncarboxaldéhyde ; ou (ttt) le p-méthylphénoxyacétaldéhyde.

3. Le précurseur de parfum selon la revendication 1, dans lequel la cétone est au moins une cétone choisie parmi : (a) l’alpha-damascone ; ou (b) la bêta-damascone ; ou (c) la delta-damascone ; ou (d) la bêta-damascénone ; ou (e) la muscone ; ou (f) la 6,7-dihydro-1,1,2,3,3-pentaméthyl-4(5H)-indanone ; ou (g) le cashmeran ; ou (h) la cis-jasmone ; ou (i) la dihydrojasmone ; ou (j) l’alpha-ionone ; ou (k) la bêta-ionone ; ou (I) la dihydro-bêta-ionone ; ou (m) la gamma-méthyl ionone ; ou (n) l’alpha-iso-méthyl ionone ; ou (o) la 4-(3,4-méthylènedioxyphényl)butan-2-one ; ou (p) la 4-(4-hydroxyphényl)butan-2-one ; ou

(q) la cétone de bêta-naphthyle de méthyle ; ou (r) la cétone de méthyle cédryle ; ou

(s) la 6-acétyl-1,1,2,4,4,7-hexaméthyle tétraline (tonalide) ; ou (t) la 1-carvone ; ou (u) la 5-cyclohexadécèn-1-one ; ou (v) l’acétophénone ; ou (w) la décatone ; ou (x) la 2-[2-(4-méthyl-3-cyclohexényl-1-yl)propyl]cyclopentan-2-one ; ou (y) la 2-sec-butylcyclohexanone ; ou (z) la bêta-dihydro ionone ; ou (aa) l’allyl ionone ; ou

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5 10 15 20 25 30 35 40 45 50 55 (bb) l’alpha-irone ; ou (cc) l’alpha-cétone ; ou (dd) l’alpha-irisone ; ou (ee) l’acétanisole ; ou (ff) l’acétone de géranyle ; ou (gg) la 1-(2-méthyl-5-isopropyl-2-cyclohexényl)-1-propanone ; ou (hh) le diisoamylène d’acétyle ; ou

(ii) la cyclocitrone de méthyle ; ou (jj) la 4-t-pentyl cyclohexanone ; ou (kk) la p-t-butylcyclohexanone ; ou (ll) la o-t-butylcyclohexanone ; ou (mm) la cétone d’éthyle amyle ; ou (nn) la cétone d’éthyle pentyle ; ou (oo) la menthone ; ou

(pp) la méthyl-7,3-dihydro-2H-1,5-benzodioxépine-3-one ; ou (qq) la fenchone ; ou

(rr) la cétone de méthyle naphtyle ; ou (ss) la cétone de propyle naphtyle ; et (tt) la cétone de méthyle hydroxynaphtyle.

4. Un système de libération d’un composé précurseur de parfum comprenant :

(a) au moins 0,001% en poids du composé précurseur de parfum selon la revendication 1 capable de libérer une matière première de parfum ; et

(b) pour le reste, des véhicules et des ingrédients additifs. 5. Un détergent de lessive comprenant :

(a) au moins 0,001% en poids du composé précurseur de parfum selon la revendication 1 capable de libérer une matière première de parfum ;

(b) une quantité efficace d’un agent tensioactif détersif ; et (c) pour le reste, des véhicules et des ingrédients additifs.

6. Un assouplissant pour textile ou une lingette assouplissante pour sèche-linge comprenant :

(b) une quantité efficace d’un composé d’assouplissant pour textile ; et (c) pour le reste, des véhicules et des ingrédients additifs.

7. Un parfum ou un parfum fin comprenant :

(b) entre 0,01% et 99% en poids d’un adjuvant de matières premières de parfum ; et (c) pour le reste, des véhicules et des ingrédients additifs.

8. Un produit de soins personnels ou un produit de soins buccaux ou un produit d’entretien de surfaces dures comprenant :

(b) au moins 0,1% en poids d’un agent tensioactif ou émollient ou abrasif ou anti-bactérien convenant pour être utilisé dans les produits de soins personnels, de soins buccaux ou d’entretien de surfaces dures ; et

(c) pour le reste, des véhicules et des ingrédients additifs.

9. Un procédé pour la préparation d’un composé de précurseur de parfum selon la revendication 1, comprenant la réaction de l’aldéhyde ou de la cétone et de X-OH.

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REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description • WO 0072816 A [0004] • WO 02057400 A [0006] • US 20030045447 A [0007] • WO 9827190 A [0008] • WO 9900347 A [0009] • US 5501806 A [0036]