Functional fragrance precursor

Description of the invention

The present invention relates to a class of compounds, and in particular to a group of perfume precursor compounds, which are used to impart a fragrance effect, particularly on surfaces such as fiber surfaces, skin, hair and hard surfaces. More particularly, the invention relates to a group of perfume precursor compounds which decompose on the above-mentioned surfaces and consequently give off a fragrance. In preferred embodiments, the invention provides certain hemiacetal and acetal compounds. Since the fragrance or perfume is released only when the compounds according to the invention decompose, the compounds according to the invention can provide a long lasting fragrance effect. That is, the compounds of the invention provide a sustained release of the fragrance.

A further aspect of the invention relates to a process for the preparation of these precursor compounds. The perfume precursor compounds are composed of perfume raw materials and functional compounds such as surfactants, polymers, etc. which have advantages such as surface protection, surface conditioning and / or surface cleaning.

The present invention furthermore relates to compositions containing the compounds of the present invention and to perfume raw material delivery systems which provide extended fragrance benefits.

From patent application WO 00/72816 there are known perfume delivery systems which contain pro-odor and pro-harmonizing agents selected from at least two of the following groups: (i) aldehyde or ketone-releasing pro-odor agents, the pro-odor agents containing, inter alia, and preferably oxazolidines , (ii) β-amine perfumes and (iii) ortho ester pro-harmonizing agents. The described pro-odors are suitable for delivering aldehydes and ketones of fragrance raw materials, in particular to human skin. More specifically, said international patent application is based on the discovery that certain aldehyde aroma raw materials, such as para-t-bucynal, cymal and lillial, can be released in a controlled manner from specific heterocyclic pro-odor agents, especially to the skin.

Fragrance additives are included in laundry products, such as fabric softeners or detergents, which give said products a more aesthetic user experience. The product should not only smell pleasant and thus increase the perception of the purchase, but also impart a pleasant and advantageously long-lasting fragrance to the treated fibers or fabrics. One problem faced by one skilled in the art is that the amount of fragrance transferred is rather marginal, a significant proportion of the fragrance is lost on washing and disappears on drip. Hence, it would be desirable to find ways to more effectively deliver fragrance or fragrances to fibers, fabrics and textiles and to obtain a fragrance effect over an extended period of time.

Colgate-Palmolive Patent Application No. WO 02/057400 discloses a water-soluble, cross-linked cationic polymer derived from polymerization from 5 to 100 mole% of a cationic vinyl addition monomer, from 0 to 95 mole% acrylamide and from 70 to 300 ppm of an agent. a crosslinker based on a difunctional vinyl addition monomer that increases the delivery of perfume from the fabric softening composition to the fabric softening.

From pending Colgate-Palmolive patent application Serial No. US 9/893117, filed June 27, 2001, there is known a fabric care composition consisting of a cationic softening compound, an unlimited perfume oil and at least one fabric benefit component or skin, such as perfume oil, contained in pressure-sensitive capsules to provide enhanced delivery of such benefit ingredient to the fabric.

The first object of the present invention is to provide alternative perfume or pro-odor precursors.

Another object is to provide a more effective system for delivering a fragrance or fragrance to a surface.

A still further object is to develop functional perfume precursor compounds that impart long lasting fragrance benefit especially to fiber containing materials such as laundry fabrics and linen.

Moreover, it is an object of the present invention to provide a controlled or sustained release system that releases the fragrance over an extended period of time.

A still further object of the invention is to provide consumer product compositions that can provide a sustained release of the fragrance.

PL 209 349 B1

Other objects of the invention will become apparent from reading the following description and are achieved in particular in the case of laundry products, personal care products, hard surface care products, mouth products, etc.

In accordance with the present invention, a class of chemicals has been established, and in particular a class of perfume precursor compounds, which form the basis of products and methods that meet at least some of the above-identified purposes.

More particularly, the present invention provides perfume precursor compounds which can decompose under ambient conditions and which are the product of the reaction between a hydroxyl compound, X-OH, and an aldehyde or ketone. More particularly, the invention relates to a perfume precursor compound consisting of one or more compounds derived from the reaction of X-OH and an aldehyde or ketone, the perfume precursor compounds having the formula XOC (R) (R *) (OR **), wherein R is a C6-24alkyl group, a C6-24aralkyl group or a C6-24alkylaryl group, R * is H or a C6-24alkyl group, a C6-24aralkyl group or a C6-24alkylaryl group , R ** is H or X, wherein XO is a moiety derived from X-OH, where X-OH is a compound selected from the group consisting of surfactants, fabric softeners, estramines, emollient precursors, amidoamines, emollient precursors, hair conditioners, skin conditioners, saccharides and polymers.

In preferred embodiments, X-OH has the following structure:

AND.

Ri

AND

R₂-Y- (CH₂)_q- (Q)_m-B where R1 and R2 are independently H or:

(a) a C1-C22-alkylene carboxyl moiety of the formula - (CH2) eR3, wherein R3 is -NHCOR4 or -OCOR4 or -NR5COR4, and wherein R4 and R5 are independently C1-C22-alkyl or -alkenyl, and e is an integer from 1 to 22, or (b) linear or branched C1-C22-alkyl or (c) linear or branched C1-C22-alkenyl or (d) substituted or unsubstituted C2-C22-alkyleneoxy or (e) substituted or unsubstituted alkyleneoxy-C3-C22- alkyl or (f) substituted or unsubstituted C6-C22-aryloxy or (g) substituted or unsubstituted C7-C22-alkylenearyl or (h) substituted or unsubstituted C7-C22-alkyleneoxyaryl or (i) C7-C22-oxyalkylenearyl or (i) ) anionic unit with the formula:

- (CH2) yR6 where R6 is -SO3M, -OSO3M, -PO3M, -OPO3M, Cl or mixtures thereof, where M is hydrogen or one or more salt-forming cations sufficient to maintain a charge balance, or a mixture thereof, y is an integer from 1 to about 22 or (k) a mixture of at least two (a) to (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.

II.

OO

II II

R₁-CT- (CH₂)_m-N- (CH₂)_n-TCR₂AND

R₃ where R1 and R2 are independently aliphatic C12-C30 hydrocarbyl groups, R3 is (CH2CH2O) pH, CH3 or H, T is 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.

PL 209 349 B1

III.

R1-Y- (CH2) q- (Q) mB wherein R1 is H or (a) a C1-C22-alkylene carboxyl moiety of the formula - (CH2) eR3, wherein R3 is -NHCOR4 or -OCOR4 or -NR5COR4, and wherein R4 and R5 are independently C1-C22-alkyl or -alkenyl and e is an integer from 1 to 22, or (b) linear or branched C1-C22-alkyl or (c) linear or branched C1-C22-alkenyl or (d) substituted or unsubstituted C2-C22-alkyleneoxy or (e) substituted or unsubstituted alkyleneoxy-C3-C22- alkyl or (f) substituted or unsubstituted C6-C22-aryloxy or (g) substituted or unsubstituted C7-C22-alkylenearyl or (h) substituted or unsubstituted C7-C22-alkyleneoxyaryl or (i) C7-C22-oxyalkylenearyl or (j ) anionic unit with the formula:

- (CH2) yR6 where R6 is -SO3M, -OSO3M, -PO3M, -OPO3M, Cl or mixtures thereof, where M is hydrogen or one or more salt-forming cations sufficient to maintain a charge balance, or a mixture thereof, y is an integer from 1 to about 22, and (k) a mixture of at least two (a) to (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 O or S.

IV.

<img file="PL209349B1_D0001.tif" />

wherein R1 and R2 are independently H or (a) a C1-C22-alkylene carboxyl moiety of the formula - (CH2) eR3, wherein R3 is -NHCOR4 or -OCOR4 or -NR5COR4, and wherein R4 and R5 are independently C1-C22 -alkyl or -alkenyl and e is an integer from 1 to 22, or (b) linear or branched C1-C22-alkyl or (c) linear or branched C1-C22-alkenyl or (d) substituted or unsubstituted C2-C22-alkyleneoxy or (e) substituted or unsubstituted alkyleneoxy-C3-C22- alkyl or (f) substituted or unsubstituted C6-C22-aryloxy or (g) substituted or unsubstituted C7-C22-alkylenearyl or (h) substituted or unsubstituted C7-C22-alkyleneoxyaryl or (i) C7-C22-oxyalkylenearyl or (i) ) anionic unit with the formula:

- (CH2) yR6 where R6 is -SO3M, -OSO3M, -PO3M, -OPO3M, Cl or mixtures thereof, where M is hydrogen or one or more salt-forming cations sufficient to maintain a charge balance, or a mixture thereof, R6 may also be chloride, and y is an integer from 1 to about 22, and (k) a mixture of at least two (a) to (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),

PL 209 349 B1

R7 is independently hydrogen, methyl, ethyl, propyl or benzyl, and mixtures thereof, B is H or OH, Y is C or N, R8 is H or C1-C4-alkyl,

WITH^- is a counter-anion, in particular methyl chloride or sulfate.

V.

<img file="PL209349B1_D0002.tif" />

wherein R1 and R2 are as defined in I, R 'and R "are independently OH or R1, provided that at least one of R' and R" is OH.

In a second aspect, the present invention relates to a process for the preparation of products according to the invention which comprises the reaction of an aldehyde or ketone and a compound X-OH, X-OH being defined as above.

In a third aspect, the present invention provides an aqueous perfume delivery composition containing one or more of the reaction products of the invention. Preferably, said composition comprises a fabric softener.

In the drawings:

Fig. 1 shows the reaction between two fatty amidoamine and a C10-aldehyde,

Figure 2 shows the perfume release from a fabric treated with a fabric softener containing perfume precursor compounds of the present invention after 1 and 5 days for C8-, C9- and C10-aldehydes by GC / MS solid phase microextraction.

Fig. 3 shows the GC / MS spectrum of pure C10-aldehyde and compound isolated from a fabric treated with a perfume precursor compound based on C10-aldehyde and Varisoft 510.

13

Figures 4a-4b show spectra ¹H-NMR and spectra ¹³C-NMR of Varisoft 510 and Varisoft 510 reacted with the C10-aldehyde, a

Figures 5a-5c show the mass spectrum of the reaction products of Varisoft 510 with a C10-aldehyde.

As mentioned above, the present invention relates to the product of the reaction between X-OH and an aldehyde or ketone. In the aldehyde or ketone starting materials of this reaction, the C6-24alkyl moiety includes linear and branched alkyl groups which may have one or more unsaturations. Such groups may be substituted with substituents that do not adversely affect the aromatic activity of the aldehyde or ketones. Examples of such substituents include F, Cl and OH.

The C6-24 alkylaryl and -arylalkyl moiety may also be branched and contain substituents which do not adversely affect odorous properties.

In an even more preferred embodiment, X-OH preferably has the following structure:

Ri

AND

R₂-Y- (CH₂)_q- (Q)_m-B where R1 and R2 are independently H or:

(a) a C1-C22-alkylene carboxyl moiety of the formula - (CH2) eR3, wherein R3 is -NHCOR4 or -OCOR4 or -NR5COR4, and wherein R4 and R5 are independently C1-C22-alkyl or -alkenyl, and e is an integer from 1 to 22, or (b) linear or branched C1-C22-alkyl or (c) linear or branched C1-C22-alkenyl or (d) substituted or unsubstituted C2-C22-alkyleneoxy or (e) substituted or unsubstituted alkyleneoxy-C3-C22- alkyl or (f) substituted or unsubstituted C6-C22-aryloxy or (g) substituted or unsubstituted C7-C22-alkylenearyl or

(H) a substituted or unsubstituted C7-C22-alkyleneoxyaryl or (i) a C7-C22-oxyalkylenearyl or (j) an anionic unit of the formula:

- (CH2) yR6 where R6 is -SO3M, -OSO3M, -PO3M, -OPO3M, Cl or mixtures thereof, where M is hydrogen or one or more salt forming cations sufficient to maintain a charge balance, or a mixture thereof, y is an integer from 1 to about 22, or (k) a mixture of at least two (a) to (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.

Aldehydes useful in the present invention may be one or more aldehydes, but are not limited to, selected from the following group of aldehydes:

(a) phenylacetaldehyde or (b) p-methylphenylacetaldehyde or (c) p-isopropylphenylacetaldehyde or (d) methylnonylacetaldehyde or (e) phenylpropanal or (f) 3- (4-tert-butylphenyl) -2-methylpropanal or (g) 3 - (4-t-butylphenyl) propanal or (h) 3- (4-methoxyphenyl) -2-methylpropanal or (i) 3- (4-isopropylphenyl) -2-methylpropanal or (j) 3- (3,3- methylenedioxyphenyl) -2-methylpropanal or (k) 3- (4-ethylphenyl) -2,2-dimethylpropanal) or (l) phenylbutanal or (m) 3-methyl-5-phenylpentanal or (n) hexanal or (o) trans-2-hexenal or (p) cis-hexen-3-al 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-hydrooctane-1- al or (cc) nonanal or (dd) 6-nonenal or (ee) 2,4-nonadiene or (ff) 2,6-nonadienal or (gg) decanal or (hh) 2-methyldecanal or (ii) 4-decenal either (jj) 9-decenal or (kk) 2,4-decadienal or (II) undecanal or (mm) 2-methyldecanal or (nn) 2-methyloundecanal or (oo) 2,6,10-trimethyl-9-undecenal or (pp) undecene-10-ylaldehyde or (qq) undecene-8-al or (rr) dodecanal or

PL 209 349 B1 (ss) tridecanal or (tt) tetradecanal or (uu) anisaldehyde or (vv) bourgenonal or (ww) cinnamaldehyde or (xx) α-amylcinnamaldehyde or (yy) α-hexylcinnamaldehyde or (zz) methoxycinnamaldehyde or (aaa) citronellal (bbb) hydroxycytronellal or (ccc) isocyclocytral or (ddd) citronellyloxyacetaldehyde or (eee) cortexaldehyde or (fff) cumaldehyde or (ggg) cyclamenaldehyde or (hhhropin or (iii) heydraljropin or (iii) heydraljropin ) hydrotropic aldehyde or (kkk) lilial or (III) vanillin or (mmm) ethylvanillin or (nnn) benzaldehyde or (ooo) p-methylbenzaldehyde or (ppp) 3,4-dimethoxybenzaldehyde or (qqq) 3- and 4- (4-) hydroxy-4-methylpentyl) -3-cyclohexene-1-caroxaldehyde or (rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde or (sss) 1-methyl-3-4-methylpentyl-3-cyclohexene carboxaldehyde and (ttt) p-methylphenoxyacetaldehyde.

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

Ketones useful in the present invention can be one or more ketones, but are not limited to, selected from the group of the following ketones:

(a) alpha-damascone or (b) beta-damascone or (c) delta-damascone or (d) beta-damascone or (e) muscone or (f) 6,7-dihydro-1,1,2,3, 3-pentamethyl-4 (5H) indanone or (g) cashmeran or (h) cis-jasmon or (i) dihydrojasmone or (j) alpha-ionone or (k) beta-ionone or (l) dihydro-beta-ionone or (m) gamma-methyl ionone or (n) alpha-isomethyl ionone or (o) 4- (3,4-methylenedioxyphenyl) 2-butanone or (p) 4- (4-hydroxyphenyl) 2-butanone or (q) methyl beta - naphthylketone or (r) methylcedrylketone or (s) 6-acetyl-1,1,2,4,4,7-hexamethyltetralin (tonalide) or (t) 1-carvone or (u) 5-cyclohexadecen-1-one or (v) acetophenone or (in ) decaton or (x) 2- [2- (4-methyl-3-cyclohexen-1-yl) propyl] cyclopentanone-2 or (y) 2-sec-butylcyclohexanone or

PL 209 349 B1 (z) beta-dihydroionone or (aa) allylionone or (bb) alpha-iron or (cc) alpha-cetone or (dd) alpha-irisone or (ee) acetanisole or (ff) geranylacetone or (gg) 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone or (hh) acetyldiisoamylene or (ii) methylcyclohexanone or (jj) 4-t-pentylcyclohexanone or (kk) pt-butylcyclohexanone or (II) ot -butylcyclohexanone or (mm) ethylamyl ketone or (nn) ethylpentyl ketone or (oo) menthone or (pp) methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one or (qq) phenchone or (rr) methylnaphthylketone or (ss) propylnaphthylketone and (mp) methylhydroxynaphthylketone.

The perfume precursor compounds of the present invention have been found to act as a source of long lasting fragrance benefit especially when applied to surfaces such as fiber, skin, hair and hard surfaces, and more particularly laundry and fabrics. More particularly, the invention relates to perfume precursor compounds that break down on surfaces such as fiber, skin, hair and hard surfaces, especially fabrics and laundry, and thereby emit fragrance.

Since the fragrance or perfume is released only when the compounds according to the invention disintegrate, the compounds according to the invention can provide a long lasting fragrance, i.e. the compounds according to the invention provide a sustained release of the perfume.

According to the present invention, there is a balance between the degree of degradation of the perfume precursor compounds to form the fragrance and the degree of the fragrance. The aroma intensity is essentially based on the aroma formed.

In order to also ensure the release of the perfume after a few days, for example 5 days, in particular after 7 days, the perfume must be released by the controlled degradation of the perfume precursor compounds according to the invention. This means that the balance between the perfume precursor compounds and the perfume containing ingredients preferably has to be such that a sufficient amount of the perfume is released within a few days. This equilibrium depends on the nature of the aldehyde or ketone and the nature of the X-OH compound.

In another embodiment of the present invention, the perfume precursor compound of the invention is derived from a compound X-OH selected from the group consisting of polyalkylene glycol, polyalkylene glycol ester and polysaccharide. The polyalkylene glycol or an ester thereof is preferably based on polyethylene glycol, polypropylene glycol and polyethylene / propylene glycol.

The perfume precursor compounds of the present invention are especially intended for incorporation into surface treatment compositions such as fiber surfaces, skin, hair and hard surfaces, especially fabrics and laundry. From this point of view, it would be very desirable to have compounds which are not only compatible with the compositions used to treat such materials, but additionally have properties useful in such compositions. Therefore, in specifically preferred embodiments, the invention relates to perfume precursor compounds of the type described above, wherein X-OH is the surfactant described herein as I. A preferred structure has the formula (R1- (CH2) z) xN- (CH2) y-OH, wherein R1 is independently selected from the group consisting of a fatty amidoamine moiety of formula AlkC (O) NH-, a moiety of formula AlkC (O) O , a moiety of formula Alk-O in which Alk is a C2-C24 linear or branched alkyl or alkylene group optionally substituted with one or more hydroxyl groups, nitro groups, amino groups and / or halogen atoms, or represents a CHOH-R group, z and y are independently integers with values ​​from 0 to 10, preferably from 0 to 5 and especially from 1 to 3, and x is 2 or 3.

These perfume precursor compounds are based, for example, on fatty or bi-fatty amidoamines which themselves have fabric softening properties. Examples of such fatty amidoamines include, for example, fabric softeners sold under the Varisoft tradename such as Varisoft 510 (ex Goldschmidt, Germany), as mentioned in US-A-5501806. As will be seen from the examples below, the reaction product between the bi-fatty amidoamine (Varisoft 510) and the C8-12-aldehydes produces fragrances which provide a continuous release of aldehydes for more than 1 week.

The perfume precursor compounds of the invention can be prepared by reacting an aldehyde and / or ketone perfume and a compound X-OH, X-OH being selected from the group consisting of surfactants, fabric softeners, esteramines of fabric softener precursors, for conditioning hair and skin, and polymers. This is a further aspect of the present invention.

In fact, the formation of the acetal, hemiacetal and / or ketal is based on the use of a compound containing at least one free nucleophilic -OH group and an aldehyde and / or a ketone. This reaction is known per se and is preferably carried out in an aqueous solution in the presence of an acid or a catalyst.

Fig. 1 shows an example of the reaction between an amidoamine and a C10-aldehyde. An example of an amidoamine starting material is Varisoft 510. The products obtained from this reaction can very advantageously be incorporated into a product formula such as a fabric softener in the rinse cycle, and delivered from said formula to a surface giving it a long lasting fragrance.

Depending on the number of free hydroxyl groups, one or more molecules of an aldehyde or a ketone can be coupled to the XOH molecule, whereby the susceptibility of the perfume to release can be controlled to some extent.

In a still further aspect the invention relates to an aqueous perfume delivery composition comprising one or more perfume precursor compounds according to the invention. Preferably, said aqueous composition is a fabric softener, in particular a rinse cycle fabric softener.

Good results are obtained with the incorporation into the aqueous composition of from 0.001 to 10% by weight of the aroma saucer precursor according to the invention, based on the total weight of the composition, and the content of each fabric softening active is preferably from 0.01 dc to 35% by weight, in particular from 2% by weight. up to 15% by weight. A preferred cationic softening agent is an ester quaternary ammonium-based softening agent having the following structural formula:

<img file="PL209349B1_D0003.tif" />

where R4 is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, R2 and R3 are (CH2) s-R5, where R5 is an alkoxycarbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, phenyl substituted (C1-C4) -alkyl, OH or H, q, s and s are each independently an integer from 1 to 3, and X^- is an anion compatible with the softening agent.

The perfume precursor compound delivery system is also provided and comprises:

(a) at least 0.001% by weight of a perfume precursor conjugate consisting of:

(i) a perfume precursor compound as described herein capable of releasing a perfume raw material; and (b) carriers and additional balance components.

A laundry detergent is also provided which includes:

(a) at least 0.001% by weight of a perfume precursor conjugate consisting of:

(i) a perfume precursor compound as described herein which is capable of releasing a perfume raw material, and

(B) an effective amount of detergent surfactant; and (c) carriers and additional balance components.

A fabric softener or a fabric softening drying layer is also provided which includes:

(a) at least 0.001% by weight of a perfume precursor conjugate consisting of:

(i) a perfume precursor compound as described herein which is capable of releasing a perfume raw material, and (b) an effective amount of a fabric softener compound, and (c) carriers and additional balance components.

Also provided are perfumes or a mild fragrance which contain:

(a) at least 0.001% by weight of a perfume precursor conjugate consisting of (i) a perfume precursor compound as described herein which is capable of releasing a perfume raw material, and (b) at least 0.01 to 99% by weight of an admixture perfume raw materials; and (c) carriers and additional balance components.

A personal care product or a mouth care product or a hard surface care product is also supplied and includes:

(a) from 0.001% by weight of a perfume precursor conjugate consisting of:

(i) a perfume precursor compound as described herein which is capable of releasing perfume serums, and (b) from 0.1 wt% of a surfactant or emollient or abrasive or antimicrobial agent suitable for use in products for the preparation of a perfume. personal care or lip care or hard surface care; and (c) carriers and additional balance components.

Balance carriers and additional ingredients are selected from the group consisting of fillers, optical brighteners, bleaching agents, bleaching aids, bleach catalysts, bleach activators, soil release polymers, dye transfer agents, fluorescent agents, fabric conditioners, hydrolysing surfactants. , preservatives, antioxidants, chelating agents, stabilizers, anti-shrink agents, anti-wrinkle agents, bactericides, fungicides and anti-corrosives, and mixtures thereof.

The invention will now be described in more detail in the following examples which are not intended to limit the invention but merely illustrate it. Unless otherwise indicated, all percentages are percentages by weight based on the weight of the final composition.

Example 1

Perfume precursors can be prepared by the preferred but unlimited combination of Varisoft 510 (3.0 g) with decylaldehyde (1.8 ml), water (0.2 ml) and p-toluenesulfonic acid monohydrate (20 mg). The reaction mixture was then heated to 60 ° C in an oil bath with stirring overnight in the open air. The reaction mixture is then cooled to room temperature, and the mixture becomes a solid after standing. The spectra are given in Fig. 4¹H-NMR i ¹³C-NMR of Varisoft 510 and Varisoft 510 reacted with the C10-aldehyde. Fig. 5 shows the Mass spectrum of the reaction products.

Perfume precursors can be formed by the preferred, but not limited to, the above reaction without the addition of water.

Example 2

Fabric softener compositions were obtained containing 5% by weight of an ester quaternary ammonium compound of the following formula:

<img file="PL209349B1_D0004.tif" />

Wherein R4 is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, R2 and R3 are (CH2) s-R5, where R5 is an alkoxycarbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, phenyl substituted with (C1-C4) alkyl, OH or H, q, s and s are independently an integer from 1 to 3, and X^- represents an anion compatible with the softening agent, 1% by weight of the obtained amidoamine softener precursor compounds and 94% by weight of water. The fabric was treated with the resulting fabric softener and fragrance release was measured after 1 day and 5 days by GC / MS-coupled solid phase microextraction (SPME). For C10-aldehydes, the amount of perfume released after 1 day and after 5 days is approximately the same, indicating a desired sustained release of perfume from the fabric surface.