Functional fragrance precursor and a method of preparation

168792/2 yis nvrui mpon mnu οπρ

FUNCTIONAL FRAGRANCE PRECURSOR AND A METHOD OF PREPARATION 168792/2 TECHNICAL FIELD'

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 .

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

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

In WO-OO/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 1 168792/2 inter alia and preferably oxazolidines; (ii) a-amino pro- fragrances; and (iii) orthoester pro-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.

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. US 6395695 relates to a fragrance delivery system for use in laundry detergent compositions including rinse-added and dryer-added fabric conditioning compositions which provides a long lasting "freshness" or "clean" scent to fabric. The compositions described herein deliver highly fabric substantive linear acetal and/or ketal pro fragrances to the fabric surface during laundering wherein the pro-fragrances release their fragrance raw materials over a period of up to two weeks. US 6277796 relates to dryer-activated fabric softening compositions 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 nonionic 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. WO 98/06803 relates to rinse added fabric softening compositions containing pro fragrant acetals or ketals which hydrolyze upon exposure of surfaces rinsed in solution of said compositions to a reduction in pH, thereby releasing a fragrance which is characteristic of one or more of the hydrolysis products. 168792/1 US 3563893 describes acetals that have value as essential ingredients in hydraulic brake fluids to better meet mandatory specifications covering the performance and use thereof. WO 97/34578 describes a pro-fragrance compound selected from the group consisting of an acetal, a ketal, and mixtures thereof, wherein at least one of a parent aldehyde, ketone, or alcohol of the pro-fragrance acetal or ketal is a fragrance compound, having a CLogP of less than about 4. WO 97/34578 further discloses detergent compositions comprising the pro-fragrance compound of the present invention and detersive surfactants. GB 2359750 provides liquid malodour treatment compositions comprising a deodorizing perfume, a solubilising aid and water. The compositions are used to treat undesired odours on an item without the need for laundering. EP 0905115 describes a method for making an acetal compound, comprising the steps of: (a) adding a carbonyl compound, an alcohol, and a dehydrating agent to an environment wherein the carbonyl compound is selected from the group consisting of an aldehyde, a ketone, and mixtures thereof; and (b) pressurizing the mixture of step (a). EP 0012543 teaches that cyclic and linear acetals and ketals of fatty aliphatic aldehydes and ketones have been found to have valuable emollient properties.

Especially preferred compounds are those form mixed C13/15-aldehydes and lower alkylene glycols, glycerols and substituted glycerols, alcohols and tetritols. WO 97/34986 describes detergent compositions containing certain acetals or ketals which hydrolyze upon exposure of surfaces washed in solution of said compositions to a reduction in pH, thereby releasing a fragrance which is characteristic of one or more of the hydrolysis products.

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 frangrance delivery from a fabric softening composition to the fabric to be softened.

In copending Colgate-Palmolive U. S. Application Serial No. 9/893,117, filed June 27,2001, there is described a fabric care composition comprising a cationic softening compound; a non-confined fragrance oil; and at least one

2A 168792/2 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. OBJECTIVES OF THE PRESENT INVENTION The first objective of the present invention is to provide alternative fragrances precursors or pro-fragrances.

It is another objective to provide a more efficient delivery system of fragrance or perfume to surfaces.

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.

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.

Yet a further objective is to provide consumer product compositions which are capable to provide sustained release of fragrance.

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

It is an objective of the present invention to provide a fragrance precursor 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 Οβ_24 alkyl group, a C6.24 aralkyl group or a Cg-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-0 representing a moiety derived from X-OH, and wherein ΧΟΗ is a compqund selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, 168792/3 skin conditions, saccharides and polymers; wherein X-OH is of the following structure: R,

Rz—Y-(CH2)q— (Q)m-B wherein Ri 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 (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 oxy alkylenearyl; 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; or (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)m or (CH2CHR7O); R7 is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H if Q is (CH2CHR7O)or OH; andYisN.

Furthermore, in accordance with the present invention, the moiety - C(R)(OR**)(R*) is derived from one or more of the following aldehydes: 168792/3 (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-ethylpheny)-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-l-al; or (z) 3,7-dimethyl-l,6-octadien-3-al; or (aa) 3,7-dimethyl-6-octenal; or (bb) 3,7-dimethyl-7-hydroxyoctan-l-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 (11) 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) bourgenonal; or 168792/3 (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)cyclamem aldehyde; or (hhh)florhydral; or (iii)heliotropin; or (jjj)hydrotropic aldehyde; or (kkJk)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 -caroxaldehyde; or (rrr)2,4-dimethyl-3-cyclohexene-1 -carboxaldehyde; or (sss)l-methyl-3-4-methylpentyl-3- cyclohexencarboxaldehyde; and (ttt)p-methylphenoxyacetaldehyde.

Furthermore, in accordance with the present invention, the moiety -CHOR*-R is derived from one or more of the 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-l,l,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-ydroxyphenyl)butan-2-one; or (q) methyl beta-naphthyl ketone; or (r) methyl cedryl ketone; or (s) 6-acetyl-l,l,2,4,4,7-hexamethyltetralin (tonalid); or 168792/3 (t) 1-carvone; or (u) 5-cyclohexadecen-l-one; or (v) acetophenone; or (w) decatone; or (x) 2- [2-(4-methy 1-3 -cyclohexeny 1-1 -yl)propy 1] 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) l-(2-methl-5-isopropyl-2-cyclohexenyl)-l-propanone; or (hh) acetyl diisoamylene; or (ii) methyl cyclocitrone; or (jj) 4-t-pentyl cyclohexanone; or (kk) p-t-butylcclohexanone; or (11) o-t-butylcyclohexanone; or (mm) ethyl amyl ketone; or (nn) ethyl pentyl ketone; or (oo) menthone; or (pp) methyl-7,3-dihydro-2H-l,5-benzodioxepine-3-one; or (qq) fenchone; or (rr)methyl naphthyl ketone; or (ss) propyl naphthy ketone; and (tt) methyl hydroxynaphthyl ketone.

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises a carrier to form a fragrance precursor delivery system.

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises an effective amount of detersive surfactant to form a laundry detergent.

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises an effective amount of a fabric softening compound to form a fabric softener.

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises an effective amount of a fabric softening compound on a substrate to form a dryer sheet. 168792/3

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises 0.01% to about 99% by weight of an admixture of fragrance raw materials to form a perfume or fine fragrance.

Furthermore, in accordance with the present invention, the composition contains at least 0.0001% by weight of the fragrance precursor and further comprises at least 0.1% by weight of at least one of a surfactant, an emollient, an abrasive, or antibacterial agent to form a personal care product, an oral care product or a hard surface care product.

Furthermore, in accordance with the present invention, a method of preparing the described fragrance precursor compound comprising reacting an aldehyde or ketone fragrance of the formula R-C(O)R* and a compound represented by X-OH. Furthermore, in accordance with the present invention, the reaction is acid catalyzed.

BRIEF DESCRIPTION OF THE DRAWINGS

In the drawings,

Figure 1 shows the reaction between a difatty amido amine and a Cio 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 Cb, C9 and Cio aldehydes by Solid Phase Micro Extraction GC/MS ;

Figure 3 shows a GC/MS spectrum of pure Cio aldehyde^ and the

I compound released from cloth treated with a fragrance precursor compound based on Cio aldehyde and Varisoft 510;

<img img-format="tif" img-content="drawing" file="IL168792AD00021.tif" id="idf0001" />

Figures 4a-4d show the proton-NMR spectra and the 13C-NMR spectra of Varisoft 510 and Varisoft 510 reacted with Cio aldehyde; and

Figures 5a-5c show the Mass Spectrum of the reaction 5 products of Varisoft 510 with CIO aldehyde.

DETAILED DESCRIPTION OF THE INVENTION

As mentioned herein-above, the present invention relates to the reaction product of a reaction between X-OH and 10 an aldehyde or a ketone. In the aldehyde or ketone starting compounds of this reaction, the Cs-zt alkyl moiety encompasses linear and branched alkyl groups which can have one or more unsaturations. Such groups can be substituted with substituents which do not adversely affect the fragrance 15 activity of the aldehyde or ketones. Examples of such substituents encompass F, Cl and OH.

The Cg_24 alkaryl and aralkyl moiety can also be branched and contain substituents that do not adversely affect the fragrance properties. 20 In a more preferred embodiment, X-OH preferably is of the following structure:

Ri

R2—Y — (CHj)q— (Q)m-B 25 wherein Ri 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 Rs are each independently Ci-C22 akyl or alkenyl; 30 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 : ,'λ:·;.'. ;:·. ·. ; ; /' y; XXi.- or 5 or (e) C3-C22 substituted or unsubstituted alkylenoxy alkyl; (f) C6-C22 substituted or unsubstituted aryloxy; or (g) C7-C22 substituted or unsubstituted alkylenearyl; or (h) C7-C22 substituted or unsubstituted alkyleneoxyaryl; (i) C7-C22 oxyalkylenearyl; or (j) an anionic unit having the formula: (CTh)^ 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 15 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 20 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 CRi or N. 25 30 35 40

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-ethylpheny)-2,2dimethylpropanal; or (l) phenylbutanal; or (m) 3-methyl-5-phenylpentanal; or (n) hexanal; or 10

<img img-format="tif" img-content="drawing" file="IL168792AD00022.tif" id="idf0002" />

<img img-format="tif" img-content="drawing" file="IL168792AD00023.tif" id="idf0003" />

10 15 20 25 30 35 .40 45 (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 (aa) 3,7-dimethyl-6-octenal; or (bb) 3,7-dimethyl-7-hydroxyoctan-l-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 (II) undecana1; or (mm) 2-methyldecanal; or (nn) 2-methylundecanal; or (oo) 2,6J10-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) bourgenonal; or (ww) cinnamic aldehyde; or (xx) a-afnylcinnam-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)cyclamem aldehyde; or (hhh)florhydral; or (iii) heliotropin; or (jjj) hydrotropic aldehyde; or (kkk)lilial; or (III) vanillin; or (mmm) ethyl vanillin; or 11 50 (rmn) benzaldehyde; or (ooo)p-methyl benzaldehyde; or (ppp)3,4-dimethoxybenzaldehyde; or (qqq)3-and4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-caroxaldehyde; or (rrr)2,4-dimethyl-3-cyclohexene-l-carboxaldehyde; or (sss)1-methyl-3 -4-methylpentyl-3 -cyclohexencarboxaldehyde; and (ttt)p-methylphenoxyacetaldehyde

When an aldehyde is used the precursor of the invention is an acetal or hemiacetal.

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 (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 iorjone; or (o) 4-(3,4-methylenedioxyphenyl)butan-2-one; or (p) 4-(4-ydroxyphenyl)butan-2-one; or (q) methyl beta-naphthyl ketone; or (r) methyl cedryl ketone; or (s) 6-acetyl-l,1,2,4,4,7-hexamethyltetralin (tonalid) ; or (t) hcarvone; or (u) 5-cyclohexadecen-l-one; or (v) acetophenone; or (w) decatone; or (x) 2-[2-(4-methyl-3-cyclohexenyl-l-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-5-isopropyl-2-cyclohexenyl)-l-propanone; or (hh) acetyl diisoamylene; or 12

<img img-format="tif" img-content="drawing" file="IL168792AD00024.tif" id="idf0004" />

10 (ii) (jj) (kk)

(ID (mm) (nn) (oo) (pp) (aq) (rr) (ss) (tt) methyl cyclocitrone; or 4-t-pentyl cyclohexanone; or p-t-butylcclohexanone; or o-t-butylcyclohexanone; or ethyl amyl ketone; or ethyl pentyl ketone; or menthone; or methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one; or fenchone; or methyl naphthyl ketone; or propyl naphthy ketone; and methyl hydroxynaphthyl ketone 15 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 20 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.

Since the perfume or fragrance is only released when the compouhds of the invention are broken down, the compounds 25 of the invention are capable o'f providing a long-lasting fragrance effect. That is, the compounds of the present invention provide for a sustained release· of fragrances.

In accordance with the present invention there is a balance between the degree of breakdown of the fragrance 30 precursor compounds to form the fragrance and the intensity of the fragrance. The intensity of the fragrance is substantially based on the fragrance formed.

To guarantee also the release of fragrance after a few days, such as after 5 and preferably after 7 days, the 35 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. 13

<img img-format="tif" img-content="drawing" file="IL168792AD00025.tif" id="idf0005" />

This equilibrium depends on the type of aldehyde and or ketone and the nature of compound X-OH.

In another embodiment of the present invention, the fragrance precursor compound of the invention is derived from 5 a compound X-OH, selected from the group consisting of polyalkylene glycol, polyalkylene glycol ester and polysaccharide. Preferably, the polyalkylene glycol or the ester thereof are based on polyethylene glycol, polypropylene glycol and poly(ethylene/propylene) glycol. 10 The fragrance precursor compounds of the present invention are especially aimed to be incorporated in compositions 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 15 compounds which not only are compatible with compositions used to treat such materials, but additionally would have properties useful in such compositions. In this respect, in specifically preferred embodiments, the present invention relates to fragrance precursor compounds of the type described 20 herein-above, wherein X-OH is’a surfactant described hereinabove as I. The preferred structure is of the formula (Rx-(CH2) J χ-Ν-(CH2) y-OH, wherein Rx, independently, is selected from the group consisting of a fatty amido amine moiety of the formula AlkC(0)NH-, a moiety having the formula AlkC(0)0, a 25 moiety having the formula Alk-Ο-, wherein Aik 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, 30 preferably between 0 and 5, more preferably between 1 and 3; x represents 2 or 3.

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 14

<img img-format="tif" img-content="drawing" file="IL168792AD00026.tif" id="idf0006" />

•λ.’ : '·' ·. '·'

<img img-format="tif" img-content="drawing" file="IL168792AD00027.tif" id="idf0007" />

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 5 fatty amido amine (Varisoft 510) and CB-i2 aldehydes give profragrances that give continuous release of the aldehydes until after more than 1 week.

The fragrance precursor compounds of the invention can be obtained by reacting an aldehyde and or ketone fragrance 10 and a compound X-OH; X-OH is selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines or amido amines, hair and skin conditioners and polymers. This forms a further aspect of the present invention. 15 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 20 or a catalyst. .·

In figure 1, the reaction between an amido amine and a

Cio 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 25 product formula such as a rinse cycle fabric softener, and from said formula be delivered to a surface to give a long lasting fragrance.

Dependent on the number of free hydroxyl groups, one or more aldehyde and or ketone molecules can be coupled to the 30 XOH molecule. This makes that the capacity of fragrance to be released can be controlled to some degree.

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 15 invention. Preferable said aqueous composition is a fabric softener composition and especially a rinse cycle fabric softener composition.

Good results are obtained when incorporating between 5 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 10 is an esterquat softener having the following structural formula:

<img img-format="tif" img-content="drawing" file="IL168792AD00028.tif" id="idf0008" />

wherein R4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms, R2 and R3 represent (CH2)a-R5 15 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.

The invention will be described in more detail in the 20 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. 25 Example 1

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 16

<img img-format="tif" img-content="drawing" file="IL168792AD00029.tif" id="idf0009" />

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 13C-NMR spectra 5 are given of Varisoft 510 and of Varisoft 510 reacted with Cio aldehyde. Figure 5 shows the mass spectrum of the reaction products .

Fragrance precursors can also be formed by preferable but not limited to the above reaction without the addition of 10 water.

Example 2

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

<img img-format="tif" img-content="drawing" file="IL168792AD000210.tif" id="idf0010" />

15 wherein R4 represents an aliphatic hydrocarbon group having from 8 to 22 carbon atoms, R2 and R3 represent (CH2)3-Rs where Rs 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 20 interger 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 25 phase micro extraction (SPME) coupled with GC/MS. For Ci0 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. 17 PPti/a , cpnxan rw:n ατα inia^a pnow pnszn irn πτ qaoa ,Ρ’ηη ηχΰπ laoa-a mavia na^maa np’ioz .zruwan rwaa mpnan ρ-ίΛ oxnm □ιηπη Pi?

<img img-format="tif" img-content="drawing" file="IL168792AD000211.tif" id="idf0011" />

.(moia nannn) cras&amp;amp;'an -nwa