IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

Abstract

An encapsulated perfume composition wherein the shell contains a polyurea resin and the core contains a perfume comprising an aldehyde-containing perfume ingredient or ingredients, a non-aromatic cyclic perfume ingredient, and an alkyl salicylate and/or a 2,2,2-trisubstituted acetal,

Claims

1. An encapsulated perfume composition having a shell which contains a polyurea resin and having a core which contains a perfume comprising: an aldehyde-containing perfume ingredient, a non-aromatic cyclic perfume ingredient, an alkyl salicylate and/or a 2,2,2-trisubstituted acetal, wherein said acetal has the general formula
R.sub.1 R.sub.2R.sub.3C—CH(OR.sub.4)(OR.sub.5) wherein R.sub.1 is a saturated or unsaturated alkyl or aromatic residue having 4 to 10 carbon atoms; R.sub.2 and R.sub.3 are independently selected from a saturated or an unsaturated alkyl residue having at least on carbon atom; and R.sub.4 and R.sub.5 are independently selected from a methyl group and an ethyl group.

2. An encapsulated perfume composition according to claim 1 wherein the aldehyde perfume ingredient comprises from about 0.01% to about 6% by weight of the total perfume ingredients.

3. An encapsulated perfume composition according to claim 1 wherein the encapsulated perfume comprises at least 60% by weight of perfume ingredients having a solubility in water of 15000 ppm or less.

4. An encapsulated perfume composition according to claim 1 wherein the encapsulated perfume composition contains no solvent.

5. An encapsulated perfume composition according to claim 1, wherein the polyurea capsules have a volume average diameter of about 20 to about. 250 microns.

6. An encapsulated perfume composition according to claim 1 wherein the weight of the capsule shells is 5% to 40% based on the total weight of the capsules.

7. An encapsulated perfume composition according claim 1 in the form of a slurry which comprises: one or more core-shell capsules, dispersed in an aqueous dispersing medium, wherein the core contains a perfume and the shell contains a polyurea resin, and wherein the capsules are in the form of a stable suspension having a viscosity of up to 3000 centipoise, when measured at a shear rate of 21 s.sup.−1 at a temperature of 25° C.

8. An encapsulated perfume composition according to claim 7 wherein the aqueous dispersing medium contains a hydroxyethyl cellulose dispersing aid.

9. An encapsulated perfume composition according to claim 7 wherein the hydroxyethyl cellulose is present in amounts of about 0.05 % wight to about 1.0% wight based on the total weight of the slurry.

10. An encapsulated perfume composition according to claim 9 wherein the hydroxyethyl cellulose is a Natrosol™ hydroxyethyl cellulose.

11. A consumer product comprising an encapsulated perfume composition according to claim 1.

12. A consumer product according to claim 11, which is a leave-on personal care product.

13. A leave-on product according to claim 10 in the form of a deodorant product.

14. A leave on product according to claim 10 in the form of an anti-perspirant.

15. An encapsulated perfume composition according to claim 1, wherein R.sub.1 is a saturated or unsaturated alkyl or aromatic residue having 5 to 10 carbon atoms.

16. An encapsulated perfume composition according to claim 1, wherein R.sub.1 is a saturated or unsaturated alkyl or aromatic residue having 6 to 10 carbon atoms.

17. An encapsulated perfume composition according claim 7, wherein the capsules are in the form of a stable suspension having a viscosity of about 150 centipoise up to 3000 centipoise, when measured at a shear rate of 21 s.sup.−1 at a temperature of 25° C.

Description

EXAMPLE 1

[0144] Microcapsules were prepared as follows:

[0145] A premix (I) comprising 25 g Polyvinyl pyrolidone K60 and 650 g water was prepared and the pH was adjusted to 10.0 using sodium hydroxide solution. Premix (II) comprises 300 g perfume to be encapsulated, 20 g Desmodur® W and 5 g Bayhydur® XP 2547 was prepared.

[0146] The two premixes were combined and emulsified at room temperature by means of a stirring device. The emulsification process was carried out to the desired droplet size. The pH of the emulsion was then adjusted to 8 using aqueous sodium hydroxide solution. Then 10 g of Lupasol® PR8515 solution was added in one step.

[0147] The reaction mixture was heated until the initiation was initiated.

[0148] The mixture was then cooled down to room temperature

[0149] An encapsulated perfume composition was obtained. The volume average capsule size distribution, obtained with light scattering measurements using a Malvern 2000S instrument, was D50=20 μm and D 90=50 μm with a shell weight 6% of total slurry weight composition. The solid content of the slurry was 40 weight %.

EXAMPLE 2

[0150] Encapsulated perfume compositions were prepared according to the methodology set forth in Example 1. The compositions contained 25% by weight of slurry of perfume compositions having ingredients specified in the Tables 1 through 5, below. The encapsulation process was described in Example 1 above. The amounts of aldehydes, non-aromatic cyclic perfumer ingredients and alkyl salicylates contained in the perfumes are shown (parts by weight of the perfume). The balance of the perfume is formed from other perfume ingredients commonly used in perfumery.

[0151] The compositions of the perfumes used in the example are listed in Tables 1 to 5. Under “ionone family” is meant ionones, irones, isoraldeines, damascones, damascenone, galbanone, and the like.

TABLE-US-00001 TABLE 1 Perfume 1 composition Non- aromatic Other cyclic Alkyl Alde- ingredients ingredients salicyclates hydes AROMATIC ESTERS 3 NON-CYCLIC NON- 7 AROMATIC ESTERS ALKYL CARBONATES 1.5 DIMETHYL BENZYL 2 CARBINYL ACETATE AGRUMEX 5 PARA-ANISALDEHYDE 0.3 TERPENE ALCOHOLS 22 TERPINEOL 2 TERPENYL ACETATE 2 CITRONELLYL NITRILE 1 IONONE FAMILY 10.7 EUCALYPTOL 0.8 FLOROSA 5 GARDOCYCLENE 1 INDOFLOR 0.3 ISO E SUPER 10 JASMONE FAMILY 1 MAYOL 2 AROMATIC ALCOHOL 5 MENTHONE 0.3 LACTONES 0.5 HEXYL SALICYCLATE 10 RADJANOL 2 AROMATIC ETHERS 0.3 ROSE OXIDE 0.3 MACROCYCLIC MUSKS 5 TOTAL 44.1 45.6 10 0.3

TABLE-US-00002 TABLE 2 Perfume 2 composition Non- aromatic Other cyclic Alkyl Alde- ingredients ingredients salicyclates hydes AROMATIC ESTERS 3 NON-CYCLIC NON- 8 AROMATIC ESTERS ALKYL CARBONATES 3 BORNYL ACETATE 3 ALDEHYDE C 12 MNA 1 FLORALOZONE 1 TERPENE ALCOHOLS 37 KETALS 5 LEMONILE 0 IONONE FAMILY 3 CAMPHRE 2 PHENOLS 0 JASMACYCLENE 2 ISO E SUPER 10 AROMATIC ALCOHOL 4 CIS-3-HEXENYL 3 SALICYLATE HEXYL SALICYCLATE 10 AROMATIC ETHERS 0 MACROCYCLIC MUSKS 5 TOTAL 59 26 13 2

TABLE-US-00003 TABLE 3 Perfume 3 composition Non- aromatic Other cyclic Alkyl Alde- ingredients ingredients salicyclates hydes AROMATIC ESTERS 8 NON-CYCLIC 15 NON-AROMATIC ESTERS ALKYL CARBONATES 2 PARA TERT BUTYL 5 CYCLOHEXYL ACETATE AGRUMEX 8 TERPENE 11 ALCOHOLS FLORHYDRAL 2 HELIOTROPINE 1 IONONE FAMILY 8 FLOROCYCLENE 6 & HERBANATE INDOFLOR ISO E SUPER 4 JASMONE 2 FAMILY AROMATIC 1 ALCOHOL LACTONES 5 MACROCYCLIC MUSKS 5 PHENOLS 0.2 HEDIONE 16 NECTARYL 2 TOTAL 38 60 0 2

TABLE-US-00004 TABLE 4 Perfume 4 composition Non- aromatic Other cyclic Alkyl Alde- ingredients ingredients salicyclates hydes NON-CYCLIC NON- 16.0 AROMATIC ESTERS ALLYL CYCLOHEXYL 2.0 PROPIONATE AGRUMEX 35.4 ALCOHOLS 3.0 LILIAL 5.0 IONONE FAMILY 1.1 JASMACYCLENE 20.0 LACTONES 10.0 CIS-3-HEXENYL 2.0 SALICYLATE NECTARYL 5.0 TOTAL 19.0 73.5 2.0 5.0

TABLE-US-00005 TABLE 5 Perfume 5 composition Non- aromatic Other cyclic Alkyl Alde- Acetals ingredients ingredients salicyclates hydes (1) AROMATIC 3.4 ESTERS NON-CYCLIC 6.0 NON-AROMATIC ESTERS ALKYL 4.8 CARBONATES DIMETHYL 6.0 CARBINYL ACETATE ALDEHYDE C 12 0.7 MNA FLORALOZONE 1.4 TERPENE 43.4 ALCOHOLS METHYL 12.0 PAMPLEMEOUSSE CITRONELLYL 2.4 NITRILE LEMONILE 0.2 BORNYL 2.4 ACETATE INDOFLOR ISO E SUPER 12.0 CAMPHRE 1.7 SYLKOLIDE 1.0 AROMATIC 0.4 ETHERS MACROCYCLIC 0.5 MUSKS MINOR 1.4 COMPONENTS TOTAL 63.6 16.1 6.0 2.2 12.0 ( 1) 2,2,2-trisubstituted acetals

TABLE-US-00006 TABLE 6 Encapsulation performance of the perfume compositions Non- aromatic 2,2,2- Alde- cyclic i trisubstituted hydes ngredients Salicylates acetals Encapsulation Perfume 0.3 45.6 10 YES 1 Perfume 2.0 26.0 13.0 YES 2 Perfume 2.0 60.0 0 YES 3 Perfume 5.5 73.5 2.0 YES 4 Perfume 2.2 16.1 6.0 12.0 YES 5

EXAMPLE 3

[0152] A sensory test was carried out to compare the intensity of two samples of encapsulated perfume composition, formed according to the method of example 1, containing the same perfume but of two different sizes with D50 of 10 and 30 microns, overtime when in a roll-on deodorant base. The roll-on deodorants were tested on skin by a trained sensory panel. The products were assessed when freshly applied and then 2 hours, 6 hours and 10 hours after application. After 10 hours the products were also assessed after rubbing and directly from the skin.

[0153] The overall perceived intensity was assessed by the trained sensory panel using a 0-100 scale.

[0154] The panelists were instructed to smell their underarm immediately after sample application and then after 2 hours, 6 hours, 10 hours and 10 hours post rub through the t-shirt. 10 hours after application and after rub the under arms were also assessed directly from the skin.

[0155] For the rubbing assessment the panelists were instructed to move their left arm forward and their right arm backwards simultaneously whilst ensuring the upper arm rubs the side of their body and their lower arm is horizontally out in front of them. They were asked to make this movement four times in total.

[0156] Allocation of which sample was applied to which arm (left or right) was carried out according to a predetermined randomization and the panelists were always asked to assess their left underarm first. Each sample was assessed once by 21 panelists

[0157] The data were analyzed using a Student T-test. The confidence level was 95%.

TABLE-US-00007 TABLE 7 Time Shell 10 Capsule Weight (1) Time 0 Time Time Time hours Diameter (%) Initial 2 hours 6 hours 10 hours Post-rub D50 = 10 15 28 22 19 13 18 microns D50 = 30 15 38 30 23 13 20 microns D50 = 30 19 37 27 23 14 20 microns D50 = 30 23 28 23 20 13 18 microns (1) Percentage by weight based on the capsule weight (encapsulated material + shell material)

[0158] The results show a significant benefit of the capsules having a shell weight to diameter ratio of less than about 0.7.

EXAMPLE 4

[0159] A series of slurries containing polyurea capsules were formulated as disclosed in Table Band the extent of phase separation was measured after lweek at 50° C. As apparent from the results, no phase separation is observed when using hydroxyethyl cellulose (Natrosol 250HX) at 0.4% by weight, and the slurry remains pourable. All other dispersion aids fail to stabilize the slurry over the test period.

[0160] Phase separation was measured by naked eye assessment and was expressed as the ratio of the height of the water phase to the total height of the slurry.

TABLE-US-00008 TABLE 8 Natrosol Phase 1 2 3 4 5 6 250 HX separation Viscosity % % % % % % (wt %) % (cps) Slurry A 1.5 0 40 Slurry B 0.4 0 2400 Slurry C 3 0 10 Slurry D 3.5 0 10 Slurry E 1.5 0 15 Slurry F 0.5 0 30 Slurry G 2 0 40 1 = National 465; 2 = Starch B990; 3 = Tinovis CD; 4 = Ultragel 300; 5 = Rheocare TTA; 6 = Purity W

EXAMPLE 5

[0161] 90 g of an encapsulated perfume composition formed according to the procedure of example 1 was formed as a slurry. To this slurry was added 9 g of Capsul E (@ 23% in water) and lg of silica (Syloid FP 244). The slurry was agitated 30 min at 250 rpm and spray dried in a spray dryer (labplant) using an atomizer. The inlet temperature was 180° C. and the outlet temperature was 90° C. A free flowing powder was obtained with a D50 of 30 microns and 65% fragrance loading. The residual water constant was 4% by weight and the surface oil was 0.8% by weight