SOLID SOLUTIONS OF ODORIFEROUS SUBSTANCES AND FLAVORING AGENTS WITH VINYL LACTAM POLYMERS

Abstract

An optically clear, solid water-soluble formulation of odorants and flavorings comprising at least one synthetically prepared odorant and flavoring, in which the odorants and flavorings are embedded homogeneously in a polymer matrix based on polyvinyllactams.

Claims

1. An optically transparent, solid water-soluble formulation of odorants and flavorings comprising at least one synthetically prepared odorant and flavoring, in which the odorants and flavorings are embedded homogeneously in a polymer matrix based on a polyvinyllactam.

2. The water-soluble formulation according to claim 1, in the form of a solid solution of the odorants and flavorings in the polymer matrix.

3. The water-soluble formulation according to claim 1, comprising a polymer matrix based on a homopolymer of N-vinylpyrrolidone.

4. The water-soluble formulation according to claim 1, comprising a polymer matrix based on a copolymer of N-vinylpyrrolidone and vinyl acetate.

5. The water-soluble formulation according to claim 1, comprising a polymer matrix based on a graft copolymer of (i) 50 to 60 wt % N-vinyllactam, (ii) 25 to 35 wt % vinyl acetate, and (iii) 10 to 20 wt % of a polyether, with the proviso that the sum of components i), ii), and iii) is equal to 100 wt %.

6. The water-soluble formulation according to claim 1, comprising a polymer matrix based on a graft copolymer of 13 wt % polyethylene glycol MW 6000, 57 wt % N-vinylcaprolactam, and 30 wt % vinyl acetate, having an average molecular weight of 44 000 daltons.

7. The water-soluble formulation according to claim 1 comprising, as odorants and flavorings, a substance selected from the group consisting of geraniol, linalool, linalyl acetate, pyranol, geranyl acetate, anisaldehyde, citral, citronellal, lysmeral, citronellol, rose oxide, tetrahydrolinalool, hydroxycitronellal, betaionone, menthol, essential oils, cinnamaldehyde, anethole, vanillin, eugenol, cinnamon oil, carvone, piperonal, and complex perfume or flavoring compositions.

8. The water-soluble formulation according to claim 1 comprising, as odorants and flavorings, a substance selected from the group consisting of geraniol, linalool, linalyl acetate, pyranol, geranyl acetate, anisaldehyde, citral, citronellal, lysmeral, citronellol, rose oxide, tetrahydrolinalool, hydroxycitronellal, betaionone, menthol, cinnamaldehyde, anethole, vanillin, eugenol, carvone, and piperonal.

9. The water-soluble formulation according to claim 1 obtained by melt extrusion.

10. The water-soluble formulation according to claim 1 for use as an additive for detergent and dishwashing compositions, as a cosmetic additive, in a pharmaceutical or a food supplement, in a food, or for releasing an odorant in buildings and vehicles.

11. The water-soluble formation according to claim 5 wherein the N-vinyllactam is N-vinylcaprolactam.

12. The water-soluble formation according to claim 5 wherein the polyether is polyethylene glycol.

Description

EXAMPLES

[0036] The polymer used was a graft copolymer of 13 wt % polyethylene glycol MW 6000, 57 wt % N-vinylcaprolactam and 30 wt % vinyl acetate, having an average molecular weight of 44 000 daltons, commercially available under the name of Soluplus?, BASF.

[0037] The melt extrusion was carried out using a Thermofischer Pharma 11 twin screw extruder, L/D ratio 40, screw diameter 11 mm.

[0038] The clarity was determined by means of a light microscope using a 40-fold magnification.

[0039] The color was determined according to the European Pharmacopoeia 8th Edition.

Example 1

[0040] The formulation of polymer (solid) with 13% (w/w) linalool (liquid) was extruded under the following conditions: [0041] polymer metering unit: 300 g/h [0042] linalool liquid metering rate: 45 g/h [0043] temperature of zones 5-7: 120? C. [0044] temperature of zone 8: 130? C. [0045] screw speed 200 rpm [0046] nozzle diameter 2 mm [0047] nozzle pressure: 5 bar [0048] torque: 6.9 Nm

[0049] Appearance: clear colorless extrudate, soluble in water; on dissolution in water, an odor of linalool odor is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 2

[0050] The formulation of polymer (solid) with 22% (w/w) linalool (liquid) was extruded under the following conditions: [0051] polymer metering unit: 300 g/h [0052] linalool liquid metering rate: 84 g/h [0053] temperature of zones 5-7: 120? C. [0054] temperature of zone 8: 130? C. [0055] screw speed 200 rpm [0056] nozzle diameter 2 mm [0057] nozzle pressure: 2 bar [0058] torque: 6.9 Nm

[0059] Appearance: clear colorless extrudate, soluble in water; on dissolution, an odor of linalool is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 3

[0060] The formulation of polymer (solid) with 7% (w/w) Geraniol Extra (liquid) was extruded under the following conditions: [0061] polymer metering unit: 500 g/h [0062] Geraniol Extra liquid metering rate: 39 g/h [0063] temperature of zones 5-8: 130? C. [0064] screw speed 200 rpm [0065] nozzle diameter 2 mm [0066] nozzle pressure: 16 bar [0067] torque: 7.0 Nm

[0068] Appearance: clear colorless extrudate, soluble in water; on dissolution in water, an odor of Geraniol Extra is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 4

[0069] The formulation of polymer (solid) with 13% (w/w) Geraniol Extra (liquid) was extruded under the following conditions: [0070] polymer metering unit: 300 g/h [0071] Geraniol Extra liquid metering rate: 45 g/h [0072] temperature of zones 5-7: 120? C. [0073] temperature of zone 8: 130? C. [0074] screw speed 200 rpm [0075] nozzle diameter 2 mm [0076] nozzle pressure: 11 bar [0077] torque: 7.3 Nm

[0078] Appearance: clear colorless extrudate, soluble in water; on dissolution in water, an odor of geraniol is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 5

[0079] The formulation of polymer (solid) with 20% (w/w) Geraniol Extra (liquid) was extruded under the following conditions: [0080] polymer metering unit: 300 g/h [0081] Geraniol Extra liquid metering rate: 75 g/h [0082] temperature of zones 5-7: 120? C. [0083] temperature of zone 8: 130? C. [0084] screw speed 200 rpm [0085] nozzle diameter 2 mm [0086] nozzle pressure: 8 bar [0087] torque: 7.0 Nm

[0088] Appearance: clear extrudate, soluble in water; on dissolution in water, an odor of geraniol is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 6

[0089] The formulation of polymer (solid) with 7% (w/w) L-menthol (melting of the solid menthol with subsequent liquid metering into the extrusion process) was extruded under the following conditions: [0090] polymer metering unit: 500 g/h [0091] L-menthol liquid metering rate: 38 g/h [0092] temperature of zones 5-8: 140? C. [0093] screw speed 200 rpm [0094] nozzle diameter 2 mm [0095] nozzle pressure: 24 bar [0096] torque: 6.3 Nm

[0097] Appearance: clear extrudate, soluble in water; on dissolution in water, an odor of L-menthol is perceptible. Color not more intense than B6, BY6, Y6, GY6, R6.

Example 7 (comparative Example)

[0098] Physical mixtures were prepared of polymer and in each case 5 wt %, based on weight of polymer, of odorant (L-menthol (solid), linalool (liquid) and Geraniol Extra (liquid)), in a Turbula T 2C mixer from Willy A. Bachofen AG (Basle) at 22 rpm for 10 minutes. In this case, the polymer was initially charged and the odorant added in portions.

[0099] On mixing the components, very highly sticky and lumpy masses were formed. A homogeneous formulation could not be produced in this manner.

Test 1

[0100] Determination of the Volatility of the Odorants and Flavorings from the Formulations at 40? C.:

[0101] Extruded polymer, formulations and an equivalent amount of odorant were weighed into separate dry bowls and stored at a constant temperature of 40? C., and the mass loss was determined at defined time points using an analytical balance. See also FIGS. 1 and 2

TABLE-US-00001 3 7 17 26 Formulation Start days day day day Extruded Soluplus 100.0 100.7 100.2 100.6 100.4 powder (160? C., 200 rpm, 1 kg) Extruded Soluplus 100.0 100.6 100.0 100.4 100.2 granules (160? C., 200 rpm, 1 kg)
Calculation of Released Odorant and Flavoring after Days:

TABLE-US-00002 Formulation Start 1 day 2 days 5 days 9 days 19 days 28 days Geraniol Extra (pure) 0 mg 33 mg 62 mg 123 mg 127 mg 128 mg 129 mg 7% Geraniol Extra with Soluplus, 0 mg 15 mg 15 mg 27 mg 55 mg 72 mg 91 mg powder 7% Geraniol Extra with Soluplus, 0 mg 12 mg 8 mg 16 mg 32 mg 32 mg 44 mg granules L-Menthol (pure) 0 mg 83 mg 115 mg 141 mg 141 mg 141 mg 141 mg 7% L-menthol with Soluplus 0 mg 12 mg 10 mg 29 mg 50 mg 50 mg 65 mg powder 7% L-menthol with Soluplus 0 mg 0 mg 0 mg 0 mg 14 mg 7 mg 14 mg granules Geraniol Extra (pure) 0% 22% 41% 82% 85% 85% 86% 7% Geraniol Extra with Soluplus, 0% 12% 12% 21% 43% 56% 71% powder 7% Geraniol Extra with Soluplus, 0% 10% 7% 13% 26% 26% 36% granules L-Menthol (pure) 0% 59% 82% 100% 100% 100% 100% 7% L-menthol with Soluplus 0% 11% 9% 26% 44% 44% 58% powder 7% L-menthol with Soluplus 0% 0% 0% 0% 11% 5% 11% granules

Test 2

Sustained Release of Odorants and Flavorings Due to Different Dissolution Rate of the Formulations:

[0102] Weigh an appropriate amount of formulation (aroma concentration corresponds to 100% of the saturation solubility of the aromas in water) into a 25 mL glass beaker. Add 25 mL of demineralized water and determine the dissolution rate (complete dissolution of the formulation) at room temperature while stirring.

Saturation Solubility of the Odorants and Flavorings in Water:

[0103]

TABLE-US-00003 Geraniol Extra 0.10 g/L corresponds to 2.5 mg/25 mL L-Menthol 0.397 g/L corresponds to 9.925 mg/25 mL

TABLE-US-00004 Initial weight in 25 mL Dissolution rate Formulation of demineralized water in minutes 7% Geraniol Extra with 38 mg 17 Soluplus powder 7% Geraniol Extra with 36 mg 65 Soluplus granules 7% L-menthol with 145 mg 33 Soluplus powder 7% L-menthol with 142 mg 85 Soluplus granules