5,500,223 and 6,608,017.

Each sample was used to wash and evaluate towels. As indicate, the microcapsules of this invention are friable. This analysis indicated that the way in which ethyl vanillin was added to the fabric conditioner base) made a significant difference in fragrance intensity. In some embodiments, the friable shell-core microcapsule is composed of urea-formaldehyde, melamine-formaldehyde, phenol-formaldehyde, or amido-aldehyde. Examples of suitable emulsifiers or surfactants include, but are not limited to, lecithins, sucrose esters, proteins, gums, soap-bark extract, saponins, and the like. TABLE 2 Damp Intensity NEOBEE microcapsules only 0.81 Ethyl Vanillin only 1.31 Ethyl vanillin/NEOBEE microcapsule pre-mix 2.31 Ethyl Vanillin and NEOBEE microcapsules 1.34 (separately) Heat dry Pre-Rub NEOBEE microcapsules only 1.38 Ethyl Vanillin only 1.53 Ethyl vanillin/NEOBEE microcapsule pre-mix 2.50 Ethyl Vanillin and NEOBEE microcapsules 1.50 (separately) Heat Dry Post-Rub NEOBEE microcapsules only 1.31 Ethyl Vanillin only 1.66 Ethyl vanillin/NEOBEE microcapsule pre-mix 3.69 Ethyl Vanillin and NEOBEE microcapsules 1.59 (separately) Line dry Pre-Rub NEOBEE microcapsules only 1.31 Ethyl Vanillin only 1.18 Ethyl vanillin/NEOBEE microcapsule pre-mix 2.59 Ethyl Vanillin and NEOBEE microcapsules 1.19 (separately) Line dry Post-Rub NEOBEE microcapsules only 1.19 Ethyl Vanillin only 1.06 Ethyl vanillin/NEOBEE microcapsule pre-mix 4.19 Ethyl Vanillin and NEOBEE microcapsules 1.50 (separately) Bloom During Ironing NEOBEE microcapsules only 2.00 Ethyl Vanillin only 1.88 Ethyl vanillin/NEOBEE microcapsule pre-mix 3.00 Ethyl Vanillin and NEOBEE microcapsules 1.55 (separately). For example, in addition to ethyl vanillin or vanillin, a second fragrance can be encapsulated in the core of the microcapsule and/or provided in the friable shell-core microcapsule slurry. No.

The invention is described in greater detail by the following non-limiting examples.

Alternatively the capsules can be compromised by physical forces, such as crushing, or other methods that compromise the integrity of the capsule.

To achieve the desired concentration of ethyl vanillin and/or vanillin, the ethyl vanillin and/or vanillin can be provided in a suitable solvent such as dipropylene glycol (DPG).

At all stages the Ethyl vanillin/NEOBEE microcapsule pre-mix significantly outperformed all other samples, in particular compared with the ethyl vanillin and NEOBEE microcapsules added separately to the base. There are many other ways to make vanilla that are both natural and synthetic. 6,335,315, 5,674,832, 5,759,990, 5,877,145, 5,574,179; 5,562,849, 5,545,350, 5,545,340, 5,411,671, 5,403,499, 5,288,417, 4,767,547, 4,424,134. Moreover, a variety of solvents can be used in combination with the friable shell-core microcapsule composition of this invention.

The average outside diameter of the resulting microcapsule is in the range of from about 0.01 microns to about 1000 microns; preferably from about 0.05 microns to about 100 microns and more preferably from about 2.0 microns to about 20 microns. Ethyl vanillin (Clog P of 2.84) and vanillin are relatively water soluble fragrance ingredients. The results were compared to a reference sample where the neat fragrance and microcapsules were individually dosed directly into the fabric conditioner base. EP 13845516.7. Indeed, in accordance with this invention, when ethyl vanillin and/or vanillin is pre-mixed with a slurry of friable shell-core microcapsules, an interaction with the friable shell material is observed that allows ethyl vanillin and/or vanillin to deposit on a surface, e.g., cloth, via a wash off product thereby providing the vanilla sweet note at the damp, dry and ironing stage. Solvay, the leading producer of synthetic vanilla, makes vanillin from a by-product of rice bran oil refining. 3. TABLE 3 Mean Intensity Pre- Post- Sample Description Brush Brush 1 NEOBEE Microcapsules Only 2.98 4.00 2 Ethyl Vanillin Only 3.87 4.32 3 Ethyl Vanillin/NEOBEE 4.61 11.91 microcapsule pre-mix 4 Ethyl Vanillin and NEOBEE 3.74 4.37 microcapsules (separately).

Further suitable humectants and viscosity control/suspending agents can also be included and are disclosed in U.S. Pat. The ethyl vanillin/NEOBEE microcapsule pre-mix showed a significant benefit in strength at the post-brushing stage vs. all other samples.

Towels were washed with the microcapsule premix containing or lacking ethyl vanillin or coumarin.

Other suitable fragrances that can be combined with the ethyl vanillin or vanillin include, but are not limited to, coumarin, amyl salicylate, benzyl benzoate, benzyl salicylate, galaxolide, methyl jasmonate, and isopropyl myristate. TABLE 1 Strength Heat Dry Line Dry % In Pre- Post- Pre- Post- Base ID Rub Rub Rub Rub Damp P.O.P. Ethyl vanillin and vanillin are not typically included at large quantities in a neat oil of a fabric conditioner because they will not deposit on the cloth and will be washed away. Fragrance oils that contain Vanillin or Ethyl Vanillin will oxidize faster than fragrance oils that do not contain this ingredient. Reference samples were also prepared. The samples were applied to the forearms of the panelists in a randomized manner with one arm having Sample 1 and the other having Sample 2. Two samples were prepared in shower gel: a premix of ethyl vanillin plus pre-formed microcapsule with NEOBEE in the core (4.77% by weight) (Sample 1); and microcapsules (4.52% by weight)+ethyl vanillin solution (0.24% by weight) added separately to the shower gel (Sample 2).

The ability of the capsules of the invention to release ethyl vanillin and/or vanillin can be analyzed by conventional techniques. Each arm was evaluated 5 hours after the application for pre- and post-rub using a scale from 0-10, with 0 being the lowest and 10 being the highest on strength intensity. As used in the context of this invention, wash off products are understood to be those products that are applied for a given period of time and then are removed.

5,401,577; melamine formaldehyde microencapsulation as disclosed in U.S. Pat.

Ethyl vanillin and coumarin were separately excluded from the microcapsule premix. Therefore, this invention is a method of preparing an ethyl vanillin or vanillin friable shell-core microcapsule composition by combining ethyl vanillin and/or vanillin with preformed friable shell-core microcapsules and aging the mixture for a time sufficient for the ethyl vanillin/vanillin and microcapsules to interact. In other embodiments of the present invention, the final composition or product may be in the form of an oil, a gel, a solid stick, a lotion, a cream, a milk, an aerosol, a spray, a powder, a foam, a shampoo, a hair conditioner, a lacquer or a make-up. For this test, the premix was incorporated into a fabric conditioner, a cloth was washed with the fabric conditioner, and the cloth was evaluated at the dry stage (pre- and post-rub). A neat oil/microcapsule premix was prepared by adding ethyl vanillin (final concentration of 0.1% or 1%) and surfactant to an aqueous slurry of pre-formed microcapsules containing neobee oil, i.e., essentially unfragranced capsules.

6. Friability refers to the propensity of the capsules to rupture or break open when subjected to direct external pressures or shear forces. Methods for preparing capsules with urea formaldehyde, urea aldehyde, or amido-aldehyde are disclosed in, e.g., U.S. Pat.

A 1% mixture of ethyl vanillin plus NEOBEE microcapsules were prepared. For example, when the wash off consumer product is a fabric conditioner, the fabric conditioner can be used to wash a load of towels in either a top or front loading washing machine. The formaldehyde to melamine molar ratio of the microcapsules of this invention can be from 2.30:5.50 or as low as 0.20:0.49 (Long, et al.

The sweet note on pre- and post-rub was not present when the ethyl vanillin was absent from the formulation.

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