POWDEROUS FORMULATIONS

Abstract

The present invention relates to improved formulations of 3-nitrooxypropanol and derivatives thereof as well as to the production of such formulations.

Claims

1. A storage-stable powderous formulation comprising (i) At least 0.1 weight-% (wt-%), based on the total weight of the powderous formulation, of a compound of formula (I) ##STR00002## wherein n is an integer from 1 to 46 R.sup.1 is H, C.sub.1-C.sub.6alkyl, phenyl, OH, NH.sub.2, CN, COOH, O(CO)R.sup.8, NHC(O)R.sup.8, SO.sub.2NHR.sup.8, or ONO.sub.2, and R.sup.8 is C.sub.1-C.sub.6alkyl, phenyl, pyridyl such as preferably 2-pyridyl with the proviso that when z is >3 the hydrocarbon chain may be interrupted by O or NH. (ii) 0 wt-%-35 wt-%, based on the total weight of the powderous formulation, of an edible solvent, (iii) at least 40 wt-%, based on the total weight of the powderous formulation, of sepiolite,

2. The powderous formulation according to claim 1 further comprising (iv) 0 to 10 wt-%, based on the total weight of the powderous formulation, of water and/or an additive.

3. The powderous formulation according to claim 1 consisting of (i) 2 to 15 wt-%, based on the total weight of the powderous formulation, of a compound of formula (I), and (ii) 10 wt-% to 35 wt-%, based on the total weight of the powderous formulation, of an edible oil, and (iii) at least 60 wt-%, based on the total weight of the powderous formulation, of sepiolite, and (iv) 0 to 10 wt-%, based on the total weight of the powderous formulation, of water and/or an additive.

4. The powderous formulation according to claim 1, wherein n is an integer between 3 and 9 and R.sup.1 is OH, COOH or ONO.sub.2.

5. The powderous formulation according to claim 1 wherein the compound of formula (I) is selected from the group consisting of 3-nitrooxypropanol, 9-nitrooxynonanol, 5-nitrooxy pentanoic acid, 6-nitrooxy hexanoic acid, Bis(2-hydroxyethyl)amine dinitrate, 1,4-bis-nitrooxybutane and 1,5-bis-nitrooxypentane.

6. The powderous formulation according to claim 1 wherein the sepiolite has an average particle size D(v, 0.5) selected in the range of 100 to 1500 m.

7. The powderous formulation according to claim 1, wherein the sepiolite has an average particle size D(v, 0.5) selected in the range of 800 to 1200 m, preferably in the range of 900 to 1100 m.

8. The powderous formulation according to claim 1 wherein the edible oil is selected from the group consisting of propyleneglycol, corn oil, rapeseed oil, sunflower oil, middle chain triglyceride (MCT) and glycerol as well as mixtures thereof.

9. The powderous formulation according to claim 1 wherein the compound of formula (I) has a vapor pressure selected in the range of 0.4 to 0.8 mbar.

10. The powderous formulation according to claim 1 wherein the edible oil is propyleneglycol.

11. The powderous formulation according to claim 1 of consisting of (i) 4 to 8 wt-%, based on the total weight of the powderous formulation, of 3-nitrooxypropanol, and (ii) 20 to 30 wt-%, based on the total weight of the powderous formulation, of propyleneglycol, and (iii) at least 70 wt-%, based on the total weight of the powderous formulation, of sepiolite, and (iv) 0 to 5 wt-%, based on the total weight of the powderous formulation, of water.

12. The powderous formulation according to claim 1, wherein the powderous form contains a coating.

13. The powderous formulation according to claim 11, wherein the coating is selected from the group consisting of glycerine monostearate, carnauba wax, candelilla wax, sugarcane wax, palmitic acid, stearic acid hydrogenated cottonseed oil, hydrogenated palm oil and hydrogenated rapeseed oil as well as mixtures thereof.

14. The powderous formulation according to claim 1, wherein the retention of the compound of formula (I) is at least 70%, preferably at least 80%, most preferably at least 90%.

15. Use of formulations according to claim 1 in feed products to enhance the retention of the compound of formula (I) therein.

Description

EXAMPLES

Example 1

[0070] Particle Size Determination:

[0071] The methodology described below followed the recommendations outlined in ISO13320-1 for diffraction light scattering techniques: the particle sizes of various sepiolite grades have been measured by a Malvern Master Sizer 2000 following the recommendation of ISO13320-1. An aliquot of about 5 grams of the material tempered at 25 C.-35 to 55% r.H is sampled into the vibrator hopper of the (Sirocco) dry dispersion unit. The flow aperture of the dispenser gate is set up on the way that the product flows for 30 seconds through the measurement zone using a tygon tube, at a vibration feed rate of 50%. A sample measurement at 0.5 bar of disperser pressure is taken for 30 seconds and a snap of 30000 (on the Malvern Mastersizer 2000). The sample pass through the focused beams of light (Helium-neon laser for the red light and solid-state light source for the blue) and scatter the light allowing a measurement of particles between 0.02 and 2000 micrometers. The particle diameters in volume (as outlined in table 1), are determined using Fraunhofer approximation.

[0072] Preparation of the Formulations:

[0073] To 80 g of different type of sepiolite grades as outlined in table 1) as well as silica (silicic acid) and diatomaceous earth placed in a beaker 20 g of a 20 wt.-% 3-nitrooxypropanol solution in propyleneglycol is added under gentle agitation at room temperature. After 5 minutes agitation, the adsorption is complete and a free-flowing powder is obtained.

[0074] Stability Study:

[0075] Two aluminium bags containing 5 g of the respective formulation are stored open at 25 C. under controlled atmosphere (50% r.H). The concentration of 3-nitrooxypropanol was determined by HPLC using an Agilent High Performance Liquid Chromatography 1260 Infinity system, using an Aquasil C18, 1503 mm, 3 m column and detecting at 210 nm. The column oven was set to 23 C., the autosampler not temperature controlled. The mobile phase consisted of mobile phase A (940 mL Milli-Q-water+60 ml acetonitrile+1 mL methane sulfonic acid) and mobile phase B (800 ml Milli-Q-water+200 ml acetonitrile+1 mL methane sulfonic acid) which were used in gradient mode (0 min: 0% B, 15 min: 0% B, 15.5 min: 100% B, 21 min: 100% B, 21.5 min: 0% B, 25 min: 0% B (end of run)) with a flow of 0.4 ml/min. The results (as relative concentration to the initial value (100%)) are presented Table 2.

TABLE-US-00001 TABLE 1 Particle size Sepiolite D(0, 1) D(0, 5) D(0, 9) Sepiolite type 1 170 m 367 m 412 m Sepiolite type 2 713 m 1038 m 1486 m Sepiolite type 3 424 m 631 m 950 m

TABLE-US-00002 TABLE 2 3-Nitrooxypropanol retention (%) after Carrier 1 week 2 weeks 3 weeks 4 weeks 8 weeks 12 weeks Silicic acid 72 64 56 71 51 41 (Wuxi) 77 56 60 58 57 38 Diatomaceous earth 92 68 79 60 33 11 (Diamol) 86 64 65 38 47 18 Sepiolite type 1 103 102 100 102 99 100 (Exal H E-562) 102 99 100 100 100 95 Sepiolite type 2 106 105 106 107 100 104 (Exal 1530) 105 106 110 105 104 103 Sepiolite type 3 100 99 100 100 91 97 (Exal 3060) 100 98 101 100 93 97

[0076] As can be retrieved from table 2, the use of a sepiolite carrier results in a significantly improved retention (i.e. significantly reduced evaporation) of the active compared to a silica respectively diatomaceous earth carrier.