Improvements in or Relating to Organic Compounds

Abstract

The present invention relates to a process for obtaining an encapsulated composition, to an encapsulated composition obtainable by this process, to products comprising these encapsulated compositions and to a use of these encapsulated compositions for obtaining a consumer product.

Claims

1. A process for obtaining an encapsulated composition comprising at least one cationic core-shell microcapsule, wherein the at least one cationic core-shell microcapsule comprises a core comprising at least one functional material and a shell surrounding the core, wherein the shell comprises a resin formed by reaction of at least one trifunctional araliphatic isocyanate with at least one partially alkylated amino-aldehyde pre-condensate, the process comprising the steps of: a) Providing a core composition; b) Providing an aqueous phase comprising the at least one partially alkylated amino-aldehyde pre-condensate and a cationic stabilizing polymer; c) Emulsifying the core composition provided in step a) with the aqueous phase provided in step b) in order to obtain an emulsion of core composition droplets having a volume average size of 1 to 100 μm, preferably 5 to 50 μm, even more preferably 7 to 20 μm; d) Heating the emulsion obtained in step c) to a temperature of from 70 to 95° C., preferably from 80 to 90 ° C.; preferably at a pH of 2.0 to 4.5, more preferably of 2.5 to 4.0, still more preferably of 3.0 to 3.8, even more preferably of 3.4 to 3.6, in order to obtain core-shell microcapsules; e) Optionally: Adding a formaldehyde scavenging agent; and f) Letting the mixture obtained in step d) or step e) cool to room temperature, in order to obtain a slurry of microcapsules; wherein the at least one trifunctional araliphatic isocyanate is added to the aqueous phase or the emulsion before, during or after step c).

2. The process according to claim 1, wherein the at least one trifunctional araliphatic isocyanate is an adduct of an aliphatic triol with three araliphatic ocvanates.

3. The process according to claim 1, wherein the at least one trifunctional araliphatic isocyanate is an adduct of 2-ethylpropane-1,2,3-triol or 2-ethyl-2-(hydroxymethyl)propane-1,3-diol with a compound selected from the group consisting of 1-isocyanato-2-(isocyanatomethyl)-benzene, 1-isocyanato-3-(isocyanatomethyl)benzene and 1-isocyanato-4-(isocyanatomethyl)benzene.

4. The process according to claim 1, wherein the at least one trifunctional araliphatic isocyanate is an adduct of 2-ethylpropane-1,2,3-triol with 1-isocyanato-3-(isocyanatomethyl)benzene.

5. The process according to claim 1, wherein the at least one partially alkylated amino-aldehyde precondensate is selected from the group consisting of partially methylated polymethylol-1,3,5-triamino-2,4,6-triazine pre-condensates, partially methylated polymethylolurea, partially methylated polymethylol-benzoguanamine and partially methylated polymethylol-glycouril, more preferably partially methylated polymethylol-1,3,5-triamino-2,4,6-triazine pre-condensates.

6. The process according to claim 5, wherein the partially methylated polymethylol-1,3,5-triamino-2,4,6-triazine precondensate is obtainable by reacting melamine, formaldehyde and methanol, and wherein the molar ratio of melamine to formaldehyde is from 1:3 to 1:6 and the molar ratio of melamine to alcohol is 1:2 to 1:4.

7. The process according to claim 1, wherein the weight ratio of the at least one trifunctional araliphatic isocyanate to the at least one partially alkylated amino-aldehyde pre-condensate is 0.25 to 0.50, preferably from 0.3 to 0.4.

8. The process according to claim 1, wherein the cationic stabilizing polymer is a copolymer obtainable by copolymerizing methacrylamidopropyltrimethylammonium chloride, acrylic acid or methacrylic acid and, optionally, acrylamide.

9. The process according to claim 8, wherein the cationic stabilizing copolymer is a copolymer of 2 to 99 mol %, more particularly 30 to 95 mol %, still more particularly 60 to 90 mol %, of methacrylamidopropyltrimethylammonium chloride (MAPTAC); and 1 to 98 mol %, more particularly 5 to 70 mol %, still more particularly 10 to 40 mol %, of acrylic acid, and 0 to 50 mol %, more particularly 0.1 to 5 mol %, of acrylamide.

10. The process according to claim 1, additionally comprising the step of adding, between step d) and step f), preferably between step e) and step f), a suspending agent.

11. The process according to claim 10, wherein the suspending agent is a cationic polymer, preferably a cationic copolymer.

12. The process according to claim 1, additionally comprising the step of adding at least one preservative to the mixture obtained in step d) or to the slurry of microcapsules obtained in step f).

13. The process according to claim 1, wherein the core composition comprises at least one functional material selected from group consisting of fragrance ingredients, cosmetic ingredients, biologically active ingredients, and substrate enhancers.

14. The process according to claim 13, wherein the core composition comprises at least one fragrance ingredient selected from the group consisting of 2,6,10-trimethylundec-9-enal; 2-(tert-butyl)cyclohexyl acetate; decanal; 2-methyldecanal; undec-10-enal); undecanal; dodecanal; 2-methylundecanal; (E)-undec-9-enal; (E)-dodec-2-enal; allyl 2-(isopentyloxy)acetate; allyl 3-cyclohexylpropanoate; allyl heptanoate; 1-((2-(tert-butyl)cyclohexyl)oxy)-butan-2-ol; 1,3,4,5,6,7-hexahydro-.beta.,1,1,5,5-pentamethyl-2H-2,4a-methanonaphthalene-8-ethanol; pentyl 2-hydroxybenzoate; 1-(3,3-dimethylcyclohexyl)ethyl formate; (1R,2S,4R)-2′-isopropyl-1,7,7-trimethyl-spiro[bicyclo[2.2.1]heptane-2,4′-[1,3]dioxane]; 8-(sec-butyl)-5,6,7,8-tetra-hydroquinoline); (ethoxymethoxy)-cyclododecane; (1S,2R,5R)-2-ethoxy-2,6,6-trimethyl-9-methylene-bicyclo[3.3.1]nonane; (2S,4S)-1,7,7-trimethyl-bicyclo[2.2.1]-heptan-2-yl acetate; 1-butoxy-1-oxopropan-2-yl butyrate; 4-(tert-butyl)cyclohexyl acetate; (Z)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]-undec-4-ene; 1,1,2,3,3-pentamethyl-2,3,6,7-tetrahydro-1H-inden-4(5H)-one; 5-tert-butyl-2-methyl-5-propyl-2H-furan; (E)-3,7-dimethylocta-2,6-dienal; (E)-3,7-dimethylocta-2,6-dienal; (Z)-1,1-diethoxy-3,7-dimethylocta-2,6-diene; 3,7-dimethyloct-6-enal; 3,7-dimethyloct-6-en-1-ol 3,7-dimethyloct-6-en-1-yl acetate; 3,7-dimethyloct-6-en-1-yl formate; 3,7-dimethyloct-6-enenitrile; 3,7-dimethyloct-6-en-1-yl propionate; dodecanenitrile; 4-cyclohexyl-2-methylbutan-2-ol; (Z)-3-methylcyclotetradec-5-enone; 3-(4-isopropylphenyl)-2-methylpropanal; (allyl 2-(cyclohexyloxy)acetate; cyclohexyl 2-hydroxybenzoate; 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-carbaldehyde; (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one; (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one; (E)-1-(2,6,6-trimethyl-cyclohex-3-en-1-yl)but-2-en-1-one; (E)-dec-4-enal; 2-pentylcyclopentanone; propanedioic acid 1-(1-(3,3 -dimethylcyclohexyl)ethyl) 3-ethyl ester; 3 -methyl-2-pentylcyclopent-2-enone; 2-methyl-1-phenylpropan-2-ol ; 2-methyl-1-phenylpropan-2-yl acetate; 2-methyl-1-phenylpropan-2-yl butyrate; 4,7-dimethyloct-6-en-3-one; 2,6-dimethylheptan-2-ol; 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; (E)-4-((3 aS,7aS)-hexahydro-1H-4,7-methanoinden-5(6H)-ylidene)butanal; (E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol; ethyl hexanoate; ethyl octanoate; (E)-3,7-dimethylnona-1,6-dien-3-ol; (Z)-3,7-dimethylnona-1,6-dien-3 -yl acetate; ethyl heptanoate; ethyl 2,6,6-trimethyl cyclohexa-1,3-diene-1-carboxylate; (1s,4s)-1,3,3-trimethyl-2-oxa-bicyclo[2.2.2]octane; (2S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl acetate; (1S,2R,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol); 1-(3,5,5,6,8, 8-hexa-methyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 3-(3-isopropylphenyl)butanal; (3aR,6S,7aS)-3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl propionate; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 2-(sec-butyl)cyclohexanone); (3aS,4S,7R,7aS)-ethyl octahydro-1H-4,7-methanoindene-3a-carboxylate; 2-methyldecanenitrile; 1-(3,3 -dimethylcyclohex-1-en-1 -yl)pent-4-en-1-one; (3 aR,6S,7aS)-3a,4,5,6,7, 7a-hexahydro-1H-4,7-methanoinden-6-yl isobutyrate; (E)-3,7-dimethylocta-2,6-dien-1-ol; (E)-3,7-dimethylocta-2,6-dien-1-yl acetate; (E)-3,7-dimethylocta-2,6-2-one; 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone); 2,4,6-trimethylcyclohex-3-enecarbaldehyde; 3,5,5-dien-1-yl isobutyrate; ethyl 2-ethyl-6,6-dimethylcyclohex-2-enecarboxylate; (E)-oxacyclohexadec-12-en-2-one; methyl 3-oxo-2-pentylcyclopentaneacetate; (2S)-ethyl 3-isopropylbicyclo [2.2.1]hept-5-ene-2-carboxylate; (Z)-hex-3-en-1-yl butyrate; (E)-2-benzylideneoctanal; hexyl isobutyrate; hexyl 2-hydroxybenzoate; 4,4a,5,9b -tetrahydroindeno[1,2-d][1,3]dioxine; (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (E)-4-(2,6,6-trimethylcyclohex-2-en-1 -yl)but-3-en-2-one; (E)-4-(2,5,6,6-tetramethyl cyclohex-2-en-1-yl)but-3-en-trimethylhexyl acetate; isopropyl 2-methyl butanoate; (E)-3-methyl-4-(2,6,6-trimethyl cyclohex-2-en-1-yl)but-3-en-2-one; (3aR,6S,7aS)-3 a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-yl acetate; (Z)-3-methyl-2-(pent-2-en-1-yl)cyclopent-2-enone; (Z)-3,4,5,6,6-pentamethylhept-3-en-2-one; (Z)-1-(1-ethoxyethoxy)hex-3-ene (2E,6Z)-3,7-dimethylnona-2,6-dienenitrile; (Z)-hex-3-en-1-yl methyl carbonate; 3-(4-(tert-butyl)phenyl)-2-methylpropanal; 3,7-dimethylocta-1,6-dien-3-ol; 3,7-dimethylocta-1,6-dien-3-yl acetate; (4E)-9-hydroxy-5,9-dimethyl-4-decenal; 2-methyl-4-oxo-4H-pyran-3-yl isobutyrate; ethyl 2-methylpentanoate; 2,6-dimethylhept-5-enal; 2-isopropyl-5-methylcyclohexanol; 2-isopropyl-5-methylcyclohexanone; 1-((1S,8aS)-1,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-1H-5,8a-methanoazulen-7-yl)ethanone; undecan-2-one; methylnon-2-ynoate; 6,6-dimethoxy-2,5,5-trimethylhex-2-ene; 4-(4-methylpent-3-en-1-yl)cyclohex-3-enecarbaldehyde; 2-(2-(4-methylcyclohex-3-en-1-yl)propyl)cyclopentanone; 2-methyl-6-methyleneoct-7-en-2-yl acetate; (E)-methylnon-2-enoate; (Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate; (Z)-3,7-dimethylocta-2,6-dien-1-yl acetate; 6,8-dimethylnonan-2-ol; (Z)-non-6-enal; 3-(4-isobutyl-2-methylphenyl)propanal; 4-(tert-pentyl)cyclohexanone; 2-ethyl-N-methyl-N-(m-tolyl)butanamide; 2-methyl-4-methylene-6-phenyltetrahydro-2H-pyran; 2-cyclohexylidene-2-phenylacetonitrile; 2-cyclohexylidene-2-(o-tolyl)acetonitrile; 2,2-dimethyl-2-pheylethyl propanoate; 1-methyl-4-(4-methyl pent-3-en-1-yl)cyclohex-3-enecarbaldehyde; 6-(sec-butyl)quinoline; (E)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol; 4-(4-hydroxyphenyl)butan-2-one; 2,2,5-trimethyl-5-pentylcyclopentanone; 2,2,2-trichloro-1 -phenyl ethyl acetate); ROSALVA (dec-9-en-1-ol; (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)-methanol; 4-methylene-2-phenyltetrahydro-2H-pyran; 2-(1 -(3 ,3 -dimethyl cyclohexyl)-ethoxy)-2-methyl propyl cyclopropanecarboxylate; 3-(4-isobutylphenyl)-2-methylpropanal; 1-(spiro[4.5]dec-6-en-7-yl)pent-4-en-1-one; (E)-5 -methyl heptan-3-one oxime; (E)-6-ethyl-3 -methyl oct-6-en-1-ol; (E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl cyclopropanecarboxylate; 1-methyl-4-propan-2-ylcyclohexa-1,4-diene; 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene; 2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate; 3,7-dimethyloctan-3-ol; 2,6-dimethyloctan-2-ol; oxacyclohexadecan-2-one; (E)-tridec-2-enenitrile; (E)-4-methyldec-3-en-5-ol; 2,2,5-trimethyl-5-pentylcyclopentanone; (2,2-dimethoxyethyl)benzene and 2-(2,4-dimethylcyclohexyl)pyridine).

15. An encapsulated composition obtained by the process of claim 1.

16. A consumer product comprising the encapsulated composition according to claim 15, wherein the consumer product is a fabric care product, a home care product or a personal care product.

17. A method of obtaining a consumer product, the method comprising the step of: incorporating the encapsulated composition of claim 15 in the consumer product.

Description

EXAMPLE 1

Preparation of Microcapsules

[0081] In Example 1.1, microcapsules according to the present invention were obtained by performing the steps of: [0082] a) Preparing an aqueous phase by mixing 1.9 g of partially methylated poly-methylol-1,3,5-triamino-2,4,6-triazine precondensate (Luracoll SD, ex BASF, 70 wt.-% active content), 2.5 g of poly(methacrylamido-propyltrimethylammonium chloride-co-acrylic acid) cationic copolymer, having 71 mol-% methacrylamidopropyltrimethylammonium chloride and and 29 mol-% acrylic acid, prepared according to WO 2016/207180 A1 (Example 1), and 44 g of water; [0083] b) Adding 35.5 g of perfume (ex Givaudan) in the aqueous phase under stirring; [0084] c) Adding 0.7 g of trifunctional araliphatic isocyanate (Quix 175, ex Covestro, 75.8 wt.-% active content in ethyl acetate) to the mixture obtained in step b); [0085] d) Emulsifying the mixture obtained in step c) at a stirring speed of 950 rpm; [0086] e) Adding about 25 g of a 10 vol.-% formic acid in water to lower the pH of the emulsion to a value of 3.5±0.3; [0087] f) Heating the emulsion to a temperature of 85±5 ° C. for about 2 h; [0088] g) Letting the slurry cool to room temperature and adding about 5 g of a mixture of 20 vol.-% ammonia in water, in order to obtain a slurry of microcapsules having a pH of 5.5±0.5.

[0089] The solid content of the slurry was measured by using a thermo-balance operating at 120° C. The solid content, expressed as weight percentage of the initial slurry deposited on the balance, was taken at the point where the drying-induced rate of weight change had dropped below 0.1%/min. The ratio of the measured solid content to the theoretical solid content calculated based on the weight of perfume and encapsulating materials involved is taken as a measurement of encapsulation yield, expressed in wt.-%.

[0090] The slurry was free of agglomerate, the solid content of the slurry obtained was 43 wt.-%, the volume average size (D50) of the capsules was 10 μm, the zeta-potential was +14 mV at pH 4 and +20 mV at pH 7 and the encapsulation efficiency was 100%.

[0091] In comparative Example 1.2, microcapsules were obtained by applying the procedure disclosed in WO 2016/207180 A1, Example 1, by performing the steps of: [0092] a) Preparing an aqueous phase by mixing 1.9 g of partially methylated poly-methylol-1,3,5-triamino-2,4,6-triazine precondensate (Luracoll SD, ex BASF, 70 wt.-% active content), 0.67 g of resorcinol, and 2.5 g of poly(methacrylamidopropyltrimethylammonium chloride-co-acrylic acid) cationic copolymer, having 71 mol-% methacrylamidopropyl-trimethylammonium chloride, 29 mol-% acrylic acid, prepared according to WO 2016/207180 A1 (Example 1), and 44 g of water; [0093] b) Adding 35.5 g of perfume (ex Givaudan) in the aqueous phase under stirring; [0094] c) Emulsifying the mixture obtained in step c) at a stirring speed of 950 rpm; [0095] d) Adding about 25 g of a 10 vol.-% formic acid in water to lower the pH of the emulsion to a value of 3.5±0.3; [0096] e) Heating the emulsion to a temperature of 85±5° C. for 1 h; [0097] f) Letting the slurry cool to room temperature and adding about 5 g of a mixture of 20 vol.-% ammonia in water, in order to obtain a slurry of microcapsules having a pH of 6.2±0.5.

[0098] The resulting capsule slurry was free from agglomerates, the solid content of the slurry was 42.8 wt.-%, the volume average size (D50) of the microcapsules was 7.5 μm, the zeta-potential was +29 mV at pH 4 and +22 mV at pH 7 and the encapsulation efficiency was 100%.

[0099] In comparative Example 1.3, microcapsules were obtained by using the same process as in Example 1.1, but an anionic copolymer of ethylene and maleic anhydride was used instead of the cationic copolymer, and the trifunctional araliphatic isocyanate was dissolved in the perfume before emulsification. This was achieved by performing the steps of: [0100] a) Preparing an aqueous phase by mixing 1.9 g of partially methylated poly-methylol-1,3,5-triamino-2,4,6-triazine precondensate (Luracoll SD, ex BASF, 70 wt.-% active content), 0.8 g of poly(maleic anhydride-co-ethylene) (ZeMac E60) and 47 g of water; [0101] b) Preparing a core phase by mixing 35.5 g of perfume (ex Givaudan) and 0.7 g of trifunctional araliphatic isocyanate (Takenate D-100N, ex Mitsui) [0102] c) Adding the core phase to the aqueous phase; [0103] d) Emulsifying the mixture obtained in step c) at a stirring speed of 950 rpm; [0104] e) Reducing the stirring speed to 625±25 rpm and adding about 25 g of a 10 vol.-% formic acid in water to lower the pH of the emulsion to a value of 3.5±0.3; [0105] f) Heating the emulsion to a temperature of 90° C. for 1 h; [0106] g) Letting the slurry cool to room temperature and adding about 5 g of a mixture of 20 vol.-% ammonia in water, in order to obtain a slurry of microcapsules having a pH of 6.2 ±0.5.

[0107] The slurry was free from agglomerates, the solid content of the slurry obtained in Example 1.3 was 39.3 wt.-%, the volume average size (D50) of the microcapsules was 10 μm, the zeta-potential was −49 mV at pH 4 and −52 mV at pH 7, and the encapsulation efficiency was 100%.

Example 2

Measurement of Perfume Leakage in Model Extractive Medium

[0108] The model extractive medium was a system consisting of an aqueous solution of ethanol at an initial concentration of 30 vol.-% co-existing with an immiscible cyclohexane phase.

[0109] In a first step, 10 ml of cyclohexane are put into a vial. Second, 1.8 ml of a 30 vol.-% ethanol in water is added to the vial. After equilibration, taking into account the partition coefficient of ethanol between cyclohexane and the water of 0.03 (see A. W. Islam, A. Zavvadi, V. N. Kabadi, Chem. Process Eng. 2012, 33, 243-253), the percentage of ethanol in the aqueous phase is 25 vol.-% and the percentage of ethanol referred to the whole system is 4.6 vol.-%.

[0110] In a second step, the slurry to be assessed is diluted in such a way that the perfume concentration in the diluted slurry is 10 wt.-% and 200 μL of this diluted slurry is added to the vial.

[0111] In a third step, the vial is submitted to horizontal mixing on an elliptic xy-mixing equipment operating at a 250 rpm for 4 hours (shaking in the z direction is avoided).

[0112] In a fourth step, the upper cyclohexane phase containing the extracted perfume is analyzed spectrophotometrically by using a UV/visible light spectrometer. The perfume concentration is determined by measuring the intensity of the absorbed UV/visible light at the maximum absorbance wavelength, which has been determined previously by using a reference perfume/cyclohexane solution of known concentration. This latter reference solution is used as an external standard for the quantification of the extracted perfume. The leakage value is defined as the percentage of the encapsulated perfume that has been recovered in the hexane phase.

[0113] Representative leakage values are given in Table 1 hereunder.

TABLE-US-00001 TABLE 1 Perfume leakage in model extractive medium Leakage in wt.-% of the initial amount Sample of encapsulated perfume SAMPLE 1.1 10 SAMPLE 1.2 20 SAMPLE 1.3 59

[0114] As apparent from these results, the microcapsules obtained by applying the process according to the present invention show a lower leakage compared to the one obtained with resorcinol as cross-linker (Example 1.2). The results show also that combining a cationic stabilizing polymer and the addition of trifunctional araliphatic isocyanate in the emulsion leads to microcapsules that show significantly less perfume leakage, compared to microcapsules obtained by using an anionic stabilizing polymer with the isocyanate added to the perfume phase (Example 1.3).

Example 3

Olfactive Performance in Fabric Care Conditioner

[0115] The slurries of core-shell microcapsules obtained in Example 1.1 and 1.2 were incorporated into a model fabric care conditioner having the composition shown in Table 2. The slurry obtained in Example 1.3 was not tested due to excessive leakage. In the tests, the level of encapsulated perfume was 0.5 wt.-% based on the total weight of the conditioner. The pH of the conditioner was 3.

TABLE-US-00002 TABLE 2 Conditioner composition Ingredient Supplier INCI name Quantity [wt.-%] Calcium Chloride VWR Calcium chloride 0.5 Stepantex SP-90 Stepan Dialkylester 11.1 Ammonium Methosulfate Eumulgin CO-40 BASF PEG-40 1 Hydrogenated Castor Oil Sodium benzoate VWR Sodium benzoate 0.3 Citric acid VWR Citric acid q.s. pH 3 Water q.s. 97 Fragrance 2 Encapsulated 0.5 composition (slurry)

[0116] Terry towels were submitted to a rinse cycle in a front-loaded wash machine. The amount of conditioner was 35 g for a towel load of 1 kg and the total volume of water was 20 L.

[0117] Olfactive evaluations were performed using both freshly prepared conditioner and after aging the conditioners for one month at 37 ° C.

[0118] The pre-rub olfactive evaluation was performed on wet laundry directly out of the machine and after 4 h. For this evaluation, the terry toweling was handled carefully in order to minimize the risk of breaking the microcapsules mechanically. The post-rub olfactive evaluation was performed after line drying the terry toweling for 24 hours at room temperature. This evaluation was performed by gently rubbing one part of the terry toweling on another part of same terry toweling. The olfactive performance (intensity) has been assessed by a panel of 4 experts rated on a scale of 1-5 (1=barely noticeable, 2=weak, 3=medium, 4=strong and 5=very strong). In such evaluation, the post-rub score measures the additional impact induced by microcapsule breakage, compared to the pre-rub intensity. The results are reported on Table 3.

TABLE-US-00003 TABLE 3 Olfactive performance of encapsulated compositions 1.1 and 1.2 in laundry care conditioner Pre-rub Post-rub Pre-rub intensity Post-rub intensity intensity intensity (t = 1 month (t = 1 month Sample (t = 0) (t = 0) @ 37° C.) @ 37° C.) 1.1 2.0 2.3 2.3 2.2 1.2 2.2 2.0 1.8 2.0

[0119] As apparent form the results of Table 3, the encapsulated composition according to the present invention is at least as good as the benchmark for the freshly prepared conditioner and perform significantly better than the benchmark after the conditioner has undergone 1 month storage at 37° C.

Example 4

Measurement of Color

[0120] The difference between the coloration of microcapsule slurries of Example 1.1 and Example 1.2 with respect to calibrated white plate was measured by using a Chroma Meter CR-400/410 colorimeter. This instrument provides the a*, b*, and L* value of the so-called CIE 1976 L*a*b* color space of the Commission of Illumination, according to norm ISO/CIE 11664-4:2019(E), and the ΔE value, which describes the difference between two colors in the CIE 1976 L*a*b* color space and is given by Equation 1:

ΔE=(L*.sub.1−L*.sub.2).sup.2+(a*.sub.1−a*.sub.2).sup.2+(b*.sub.1−b*.sub.2).sup.2   (1)

[0121] The measurement was made on freshly prepared slurries and on slurries submitted to accelerated aging, combining 3 weeks storage at 50° C. and 3 days exposure to artificial sun light.

[0122] The results are reported in Table 4.

TABLE-US-00004 TABLE 4 Coloration values according to CIE 1976 L*a*b* color space of the Commission of Illumination Example L* a* b* ΔE 1.1 (t = 0) 83.72 −0.61 0.11 1.06 1.1 (aged) 82.40 −0.99 −1.01 1.6 1.2 (t = 0) 77.92 3.03 9.17 10.84 1.2 (aged) 73.89 5.12 10.02 14.55

[0123] These results show that the color of the microcapsule slurries obtained by the process of the invention is close to the white standard and that this whiteness is kept over aging, whereas the color of the reference microcapsule slurries of the comparative example is already different from the white standard at time zero and that the coloration of these latter slurries increases over aging.