Functional fragrance precursor

(54) Title: FRAGRANCE PRECURSOR COMPOUND, SAME RELEASE SYSTEM, CLOTHES WASHING DETERGENT, FABRIC SOFTENER OR FINE SOFTENING DRY SHEET, PERFUME OR FRAGRANCE FINE, PRODUCT FOR PERSONAL CARE, OR ORAL PRODUCT OR PRODUCT FOR HARD SURFACE CARE, AND METHOD OF PREPARING A FRAGRANCE PRECURSOR COMPOUND (30) Unionist Priority: 11/25/2002 us 10 / 303,287 (71) Depositor (s): Colgate-Palmolive Company (US) (72) Inventor (s): Daniel W. Smith, Amjad Farooq, Donghui Wu, Marija Heibel, Karen Drehs (74) Attorney: Momsen, Leonardos & Cia.

(86) International application: pct us2003 / 036964 of 11/19/2003 (87) International publication: wo 2004/047788 of 10/06/2004 (57) Abstract: FRAGRANCE PRECURSOR COMPOUND, SAME RELEASE SYSTEM, DETERGENT FOR CLOTHES WASHING, FABRIC SOFTENER OR TISSUE DRYING SHEET, PERFUME OR FINE FRAGRANCE, PERSONAL CARE PRODUCT, ORAL CARE PRODUCT OR HARD SURFACE CARE PRODUCT, AND, COMPOUND PREPARATION METHOD OF FRAGRANCE. The present invention relates to a class of fragrance precursor compounds comprising one or more of the compounds derived from the X-OH reaction and an aldehyde or a ketone, said fragrance precursor compounds being of the formula XOC (R) (R * ) (OR “), in which R is a Ce-24-alkyl group, a C & .24aralkyl group, or a C & ^ - alkaryl group; R * is H or a C ^-alkyl group, a C & ^-aralkyl group, or a C ^--alkaryl group, R ** is H or X; X-0 representing a group derived from X-OH, in which X-OH is a compound selected from the group consisting of surfactants, fabric softeners, fabric softener ester amines, fabric softener precursor starches: hair conditioners ; skin conditioners; saccharides and polymers. In a second aspect, it refers to a method of preparing such precursors. The invention further relates to compositions, comprising the precursor of the invention.

-1-W “FRAGRANCE PRECURSOR COMPOUND, SAME RELEASE SYSTEM, CLOTHES WASHING DETERGENT, FABRIC SOFTENER OR FINE SOFTENING DRY SHEET, PERFUME OR FRAGRANCE FINE, PRODUCT FOR PERSONAL CARE, OR ORAL PRODUCT FOR CARE OR PRODUCT FOR HARD SURFACE CARE, AND METHOD OF PREPARING A FRAGRANCE PRECURSOR COMPOUND ”

TECHNICAL FIELD

The present invention relates to a class of compounds, and especially a group of fragrance precursor compounds that are used to generate a flagrant 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 decompose on the surfaces mentioned above, 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 decomposed, the compounds of the invention are capable of providing a long-lasting fragrance effect. That is, the compounds of the present invention provide a prolonged release of flagrant. _____

In another aspect, the present invention relates to a process for preparing these precursor compounds. Fragrance precursor compounds consist of raw materials and flagrant 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 fragrant raw material delivery systems that provide extended fragrance benefits.

BACKGROUND OF THE INVENTION

In WO-OO / 72816, fragrance delivery systems are described which comprise pro-fragrances or pro-appropriates selected from at least two of the following: (i) aldehyde and ketone-releasing pro-fragrances, with the pro-fragrances being comprise inter alia and preferably oxazolidines; (ii) β-amino-pro-fragrances; and (iii) appropriate ortho-ester. The described fragrances are capable of releasing aldehydes and ketones from the fragrant raw material, especially to human skin. In more detail, the aforementioned international patent application is based on the discovery that certain fragrant raw materials of aldehyde, such as para-t-bucinal, cimal and lilial can be controlled from specific heterocyclic pro-fragrances specifically for the skin.

In products for washing clothes, such as detergents or fabric softeners, in general, perfumed additives are present which make the aforementioned products more aesthetically pleasing to consumers. The product should not only smell pleasantly and in this way increase the perception of purchase, but also give a pleasant and preferably long-lasting fragrance to the fibers or fabrics treated with it. One of the problems of the person skilled in the art is faced with the fact that the amount of perfume transport is quite marginal; a lot of fragrance is lost during washing and disappears in the drain. It would be very desirable to find more efficient means of delivering perfume or fragrances to fibers, fabrics and textile materials and to obtain the fragrance effect for a longer period of time.

Colgate-Palmolive application WO 02/057400 describes a water-soluble cross-linked cationic polymer derived from the polymerization of 5 mol to 100 mol percent of a cationic vinyl addition monomer, from 0 mol to 95 percent in mol of acrylamide, and from 70 ppm to 300 ppm of a vinyl addition monomer crosslinking agent that intensifies the fragrance release of a fabric softener composition to the fabric to be softened.

In Colgate-Palmolive US Copending Order No. 9 / 893,117, filed June 27, 2001, a fabric care composition comprising a cationic softener compound is described; an unconfined fragrant oil; and at least one beneficial ingredient for tissue or skin, such as a fragrant oil, contained within pressure-sensitive microcapsules to provide enhanced release of such beneficial ingredient to the tissue.

OBJECTIVES OF THE PRESENT INVENTION

The first objective of the present invention is to provide alternative fragrances or precursors.

Another objective is to provide a more efficient fragrance or perfume release system for surfaces.

Another objective is to provide functional fragrance precursor compounds that confer long-lasting fragrance benefits, especially for fiber-containing materials, such as fabrics and clothing.

Furthermore, an object of the present invention is to provide a controlled or extended release system releasing fragrance over a longer period of time.

Yet another objective is to provide consumer product compositions that are capable of providing prolonged fragrance release.

Other objectives will become evident 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

According to the present invention a class of chemical compounds, and especially a class of fragrance precursor compounds has been verified, which forms the basis of products and methods that meet at least a number of the objectives identified above.

More in particular, the present invention provides fragrance precursor compounds which are capable of decomposing under environmental conditions and which are the reaction product of a reaction between a hydroxylated compound, X-OH, and an aldehyde and a ketone. In more detail, the invention relates to a fragrance precursor compound comprising one or more of the compounds derived from the X-OH reaction and an aldehyde or a ketone, said fragrance precursor compounds being of the formula XOC (R) (R *) (OR **) in which R is a group C₆.24-alkyl, a C6-24-aralkyl group, or a C6-24-alkaryl group; R * is H or a group C₆24-alkyl, a C 6 -24-aralkyl group, or a C 6 -24-alkaryl group, R ** is H or X; X-0 representing a group derived from X-OH, and in which X-OH is a compound selected from the group consisting of surfactants, fabric softeners, fabric softener precursor esters, fabric softener precursor amines; hair conditioners; skin conditioners; saccharides and polymers.

In preferred embodiments X-OH is of the following structure:

I ^K R> —Y— (CHj), - (Q) „- B in which Ri and R₂ are each independently, H, or:

(a) Ci-C group₂₂-alkylene-carboxy having the formula (CH₂)_andR3 in which R₃ is -NHCOR4; or -OCOR4; or -NRsCOR ^ and in which R4 and R₅ are each independently Ci-C₂₂-alkyl or alkenyl; ee is an integer from 1 to 22; or (b) Ci-C₂₂- straight or branched alkyl; or (c) straight or branched C 1 -C 22 -alkenyl; or (d) C₂-Ç₂₂-substituted or unsubstituted alkyleneoxy; or (e) C₃-Ç₂2-substituted or unsubstituted alkylkenoxy-alkyl; or (f) C6-C₂2-substituted or unsubstituted aryloxy; or (g) C₇-Ç₂2-substituted or unsubstituted arylene alkylene; or (h) C₇-Ç₂2-substituted or unsubstituted alkylene-oxy-aryl; or (i) C₇-C22-oxy-alkylene-aryl; or (j) an anionic unit of formula:

- (CH₂)_yR, where -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or their mixtures, in which M is hydrogen, or one or more salt-forming cations sufficient to satisfy the charge balance, or its mixture;

y is an integer from 1 to about 22; or (k) a mixture comprising at least two of (a) to (j); eq is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O); R₇ it is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; eYéCRiOuN.

OO ™ -------- - - li - · ..... II ------- ----- TT _Rl_c — T- (CH₂)_m—N- (CH₂)_n—TC — R₂

Go₃ in which Ri and R₂independently represent aliphatic hydrocarbon groups C12 to C₃₀, R₃ represents (CH₂CH₂O)_PH, CH₃ or Η; 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.

III. Kt — Y - (Cfí2)_q- (Qk-B where Ri is H or;

(a) Ci-C group₂2-alkylene carboxy having the formula: (CH₂)_andR₃ in which R₃ is -NHCOR4; or -OCOR4; or -NR5COR4; and in which R4 and R₅ are each independently Ci-C₂₂-alkyl or alkenyl; ee is an integer from 1 to 22; or (b) Ci-C₂₂- straight or branched alkyl; or (c) Ci-C₂₂- linear or branched alkenyl; or (d) C₂-Ç₂₂-substituted or unsubstituted alkyleneoxy; or (e) C3-C₂₂substituted or unsubstituted alkyleneoxy-alkyl; or (f) C6-C₂₂-substituted or unsubstituted aryloxy; or (g) C₇-Ç₂₂substituted or unsubstituted alkylene-aryl; or (h) C₇-Ç₂₂substituted or unsubstituted alkylene-oxy-aryl; or (i) C₇-Ç₂₂-oxy-alkylene-aryl; or (j) an anionic unit of formula:

- (CH₂)_yR6 where R ^ is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or their mixtures, in which M is hydrogen, or one or more salt-forming cations sufficient to satisfy the charge balance, or its mixture; y is an integer from 1 to about 22; or (k) a mixture comprising at least two of (a) to (j); eq is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O); R₇ it is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and Y is O or S.

IV.

<img file="BR0316640A_D0001.tif" />

in which Ri and R₂ are each independently, H, or:

(a) C 1 -C 22 alkylene carbonoxy group having the formula: (CH₂)_andR3 in which R₃ is -NHCOR4; or -OCOR4; or -NR5COR4; and in which R4 and R₅ are each independently Ci-C₂₂-alkyl or alkenyl; ee is an integer from 1 to 22; or (b) Ci-C₂₂- straight or branched alkyl; or (c) Ci-C₂₂- linear or branched alkenyl; or (d) C₂-Ç₂₂-substituted or unsubstituted alkyleneoxy; or (e) C₃-Ç₂₂substituted or unsubstituted alkyleneoxy-alkyl; or (f) C₆-Ç₂₂-substituted or unsubstituted aryloxy; or (g) C₇-Ç₂₂substituted or unsubstituted alkylene-aryl; or (h) C₇-Ç₂₂substituted or unsubstituted alkylene-oxy-aryl; or (i) C₇-Ç₂₂-oxy-alkylene-aryl; or - (j) an anionic unit of formula: - -

- (CH₂)_yR, where Rs is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or their mixtures, in which M is hydrogen, or one or more salt-forming cations sufficient to satisfy the charge balance, or their mixture; R can also be chloride;

y is an integer from 1 to about 22; or (k) a mixture comprising at least two of (a) to (j); eq is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O); R₇ it is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and Y is C or N; R₈ is H or Ci-C₄-alkyl; Z 'is a counter-anion, and preferably chloride, or methyl sulfate.

IV.

<img file="BR0316640A_D0002.tif" />

<img file="BR0316640A_D0003.tif" />

Si-R r₂ in which Ri and R₂ are as defined in I; R 'and R are each independently OH or Rj as long as at least one of R' and R is OH.

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

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

BRIEF DESCRIPTION OF THE DRAWINGS

In the drawings,

Figure 1 shows the reaction between a digested starch-amine and a Ci aldehyde₀;

Figure 2 shows the fragrance release of fabric treated fabric softener containing the fragrance precursor compounds of the present invention after 1 day and after 5 days, for aldehydes C₈, Ç₉ and Cio by Solid Phase Microextraction coupled with GC / MS;

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

Figures 4a-4d show that proton-NMR spectra and ¹³Varisoft 510 and Varisoft 510 C-NMR reacted with C10 aldehyde; and

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

DETAILED DESCRIPTION OF THE INVENTION

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

The Ce.24-alkaryl and aralkyl group can also be branched and contain substituents that do not adversely affect the fragrance properties.

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

Laugh

Rj — Y— (Q) „- B in which Ri and R₂ are each independently, H, or:

(a) C 1 -C 22 alkylene carbonoxy group having the formula (CH₂)_andR3 in which R₃ is -NHCOR4; or -OCOR4 or -NR5COR4; and in which R4 and R₅ are each independently Ci-C₂2-alkyl or alkenyl; ee is an integer from 1 to 22; or (b) Ci-C₂2-straight or branched alkyl; or (c) Ci-C₂2-straight or branched alkenyl; or (d) C₂-Ç₂2-substituted or unsubstituted alkyleneoxy; or (e) C₃-Ç₂2-substituted or unsubstituted alkylkenoxy-alkyl; or (f) substituted or unsubstituted C6-C22-aryloxy; or (g) C₇-C22-substituted or unsubstituted alkylene-aryl; or (h) C₇-Ç₂2-substituted or unsubstituted alkylene-oxy-aryl; or (i) C₇-Ç₂2-oxy-alkylene-aryl; or (j) an anionic unit of formula:

- (CH₂)_yRó in which Ró is -SO₃M, -OSO₃M, -PO₃M, -OPO₃M, Cl or their mixtures, in which M is hydrogen, or one or more salt-forming cations sufficient to satisfy the charge balance, or its mixture; y is an integer from 1 to about 22; or (k) a mixture comprising at least two of (a) to (j); eq is an integer from 0 to about 22; m is an integer from 0 to about 22; Q is (CH₂)_m or (CH₂CHR₇O); R₇ it is independently hydrogen, methyl, ethyl, propyl or benzyl; B is H or OH; and YéCRi ouN.

The aldehydes useful in the present invention can be one or more of, but are not limited to the following group of aldehydes:

(a) Phenyl acetaldehyde; or (b) p-methyl-phenyl-acetaldehyde; or (c) p-isopropyl-phenyl-acetaldehyde; or (d) methyl-nonyl-acetaldehyde; or (e) phenyl-propanal; or (f) 3- (4-t-butyl-phenyl) -2-methyl-propanal; or (g) 3- (4-t-butyl-phenyl) -propanal; or (h) 3- (4-methoxy-phenyl) -2-methyl-propanal; or (i) 3- (4-isopropyl-phenyl) -2-methyl-propanal; or (j) 3- (3,4-methylene-dioxy-phenyl) -2-methyl-propanal; or (k) 3- (4-ethyl-phenyl-2,2dimethyl-propanal; or (l) phenyl-butanal; or (m) 3-methyl-5-phenyl-pentanal; 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-dimethyl-propanal; or (u) 2,4-heptadienal; or (v) octanal; or (w) 2-octenal; or (x) 3,7-dimethyl-octanal; or (i) 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-hydroxy-octan-1-al; or (cc) nonanal; or (dd) 6-nonanal; or (ee) 2,4-nonadienal; or (ff) 2,6-nonadienal; or (gg) decanal; or (hh) 2-methyl decanal; or (ii) 4-decennial; or (jj) 9-decennial; or (kk) 2,4-decadienal; or (11) undecanal; or (mm) 2-methyl-decanal; or (nn) 2-methyl-undecanal; or (oo) 2,6,10-trimethyl-9-undecenal; or (pp) undec-10-enyl aldehyde; or (qq) undec-8-enanal; or (rr) dodecanal; or (ss) three-channel; or (tt) tetradecanal; or (uu) anisaldehyde; or (w) bourgenonal; or (ww) cinnamic aldehyde; or (xx) α-amyl-cinnamaldehyde; or (ii) oc-hexyl cinnamaldehyde; or (zz) methoxy cinnamaldehyde; or (aaa) citronal; or (bbb) hydroxy-citronal; or (ccc) isocyclocitral; or (ddd) citronalyl-oxy-acetaldehyde; or (eee) cortexaldehyde; or (fff) cuminic aldehyde; or (ggg) aldehyde cyclamem; or (hhli) floridral; or (iii) heliotropin; or (jjj) hydrotropic aldehyde; or (kkk) lilial; or (111) vanillin; or (mmm) ethyl vanillin; or (nnn) benzaldehyde; or (ooo) p-methyl-benzaldehyde; or (ppp) 3,4-dimethoxy-benzaldehyde; or (qqq) 3-e4- (4-hydroxy-4-methyl-pentyl) -3-cyclohexene-1113 carboxaldehyde; or (rrr) 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde; or (sss) 1-methyl-3-4-methyl-pentyl-3-cyclohexene-carboxaldehyde; and (ttt) p-methyl-phenoxy-acetaldehyde

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

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

(a) alpha-damask; or (b) beta-damascona; or (c) delta-damascona; or (d) beta-damascenone; or (e) muscona; or (f) 6,7-dihydro-1,2,3,3-pentamethyl-4 (5H) -indanone; or (g) cashmerana; or (h) cis-jasmine; or (i) dihydro-jasmine; 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-methylene-dioxoxy-phenyl) butan-2-one; or (p) 4- (4-hydroxy-phenyl) butan-2-one; or (q) methyl beta-naphthyl ketone; or (r) methyl-cedryl-ketone; or (s) 6-acetyl-1,2,4,4,4,7-hexamethyl-tetralin (tonalide); 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] cyclo-pentan-2one; or (i) 2-sec-butyl-cyclohexanone; or (z) beta-dihydro-ionone; or (aa) allyl ionone; or (bb) alpha-irone; or (cc) alpha-ketone; or (dd) alpha-irisone; or (ee) acetanisol; or (ff) geranyl-acetone; or (gg) 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone; or (hh) acetyl diisoamylene; or (ii) methyl-cyclo-citrone; or (jj) 4-t-pentyl cyclohexanone; or (kk) pt-butyl-cyclohexanone; or (11) ot-butyl-cyclohexanone; or (mm) ethyl-amyl ketone; or (nn) ethyl pentyl ketone; or (oo) menthol; or (pp) methyl-7,3-dihydro-2H-1,5-benzo-dioxide-pine-3-one; or (qq) fenchone; or (rr) methyl-naphthyl-ketone; or (ss) propyl-naphthyl-ketone; and (tt) methylhydroxy-naphthyl-ketone.

The fragrance precursor compounds of the invention have been found to act as a source of long-lasting fragrance benefits, especially when applied to surfaces such as fibers, skin, hair and hard surfaces, especially on fabrics and clothing. More specifically, the invention relates to fragrance precursor compounds that decompose on surfaces such as fibers, skin, hair and hard surfaces, especially in fabrics and clothing, and as a result, release perfume.

Since the perfume or fragrance is only released when the compounds of the present invention are decomposed, the compounds of the invention are capable of providing a long-lasting fragrance effect. That is, the compounds of the present invention provide a prolonged release of fragrances.

According to the present invention there is a balance between the degree of decomposition of the precursor compounds of fragrance to form the fragrance and the intensity of the fragrance. The intensity of the fragrance is substantially based on the fragrance formed.

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

In another embodiment of the present invention, the fragrance precursor compound of the invention is derived from an X-OH compound, selected from the group consisting of poly (alkylene glycol), poly (alkylene glycol) -ester and polysaccharide. Preferably, the poly (alkylene glycol) or its ester are based on poly (ethylene glycol), poly (propylene glycol) and poly (ethylene glycol / propylene glycol).

The fragrance precursor compounds of the present invention are especially intended to be incorporated into compositions for treating surfaces such as fibers, skin, hair and hard surfaces, especially fabrics and clothing. From this perspective, it would be highly desirable for compounds to be available that are not only compatible with the compositions used to treat such materials, but additionally have useful properties in such compositions. In this regard, in especially preferred embodiments, the present invention relates to fragrance precursor compounds of the type described hereinabove, in which X-OH is a surfactant as described herein as I. The preferred structure is of formula (Ri- (CH₂)_z)_x-N- (CH₂)_y-OH, in which R_Bindependently, it is selected from the group consisting of a group of starch amine grease of the formula AlkC (O) NH-, a group having the formula AlkC (O) O, a group having the formula Alk-O-, in which Alk is a group C₂_₂₄- linear or branched alkyl or alkylene, 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.

These fragrance precursor compounds are for example based on fatty or digrax starches, which in themselves have fabric softening properties. Examples of such starch-amine greases are for example fabric softeners sold under the trade name Varisoft, such as Varisoft 510 (from Goldschmidt, Germany) as mentioned in US-A-5.501.806. As the following product follows the reaction product between a grease starch-amine (Varisoft 510) and Cg-i₂aldehydes gives products that give continuous release of aldehydes for more than 1 week.

The fragrance precursor compounds of the invention can be obtained by reacting an aldehyde and / or ketone fragrance and an X-OH compound; X-OH is selected from the group consisting of surfactants, fabric softeners, fabric softener ester amines, fabric softener precursor starches; hair conditioners; skin conditioners; saccharides and polymers. This forms another aspect of the present invention.

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

In Figure 1, the reaction between an amine-amine and a Ci aldehyde₀is shown as an example. An example of the starch amidoamine compound is Varisoft 510. The products obtained from this reaction can be very suitably incorporated into a product formula such as a fabric softener for the rinse cycle, and the aforementioned formula released to a surface to give a fragrance. long-lasting.

Depending on the number of free hydroxyl groups, one or more molecules of aldehyde and / or ketone can be copulated in the XOH molecule. This causes the fragrance capacity to be released to be controlled to some degree.

In yet another aspect, the present invention relates to an aqueous composition for the release of fragrance comprising one or more fragrance precursor compounds according to the invention. Said preferred aqueous composition is a fabric softener composition and especially a fabric softener composition for the rinse cycle.

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

~ _ +

<img file="BR0316640A_D0004.tif" />

in which R4 represents an aliphatic hydrocarbon group having 8 to 22 carbon atoms, R2 and R₃ represent (CH₂)_s-R5 in which R₅ represents an alkoxy-carbonyl group containing 8 to 22 carbon atoms, benzyl, phenyl, phenyl substituted with (C 1 -C 4 -alkyl, OH or H; q, s, et, each independently represent an integer number of 1 to 3, and X 'is a compatible anion softener.

The invention will now be described in more detail in the following examples, which do not limit the invention, but merely illustrate the invention. Unless otherwise stated, all percentages are by weight relative to the weight of the final composition.

Example 1

Fragrance precursors can preferably be formed by, but are not limited to, combining Varisoft 510 (3.0 g) with decylaldehyde (1.8 ml), water (0.2 ml) and p-toluenesulfonic acid (20 mg). The reaction was then heated in an oil bath at 60 ° C with stirring overnight open to the air. The reaction was then cooled to room temperature and solidified when at rest. In Figure 4, the proton-NMR and¹³Varisoft 510 and Varisoft 510 C-NMR reacted with Cio aldehyde- Figure 5 shows the mass spectrum of the reaction products.

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

Example 2

Fabric softening compositions are prepared comprising 5% by weight of esterquat having the structural formula:

<img file="BR0316640A_D0005.tif" />

in which R4 represents an aliphatic hydrocarbon group having 8 to 22 carbon atoms, R2 and R₃ represent (CH₂)_s-R5 in which R₅ represents an alkoxy-carbonyl group containing 8 to 22 carbon atoms, benzyl, phenyl, phenyl substituted with (Ci-C₄) -alkyl, OH or H; q, s, et, each independently represent an integer from 1 to 3; and X 'is a compatible anion softener. 1% by weight of amido-amine fragrance precursor compounds prepared; and 94% by weight of water. The fabric was treated with the fabric softener composition prepared, and the fragrance release was measured after 1 day and after 5 days by solid phase microextraction (SPME) coupled with GC / MS. For Ci aldehydes₀ the amounts of fragrance released on day 1 and day 5 are approximately equal. Showing the desired prolonged release of the fragrance from the fabric surface.

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