ADSORBATES

Abstract

The present invention relates to storage stable adsorbates of 3-nitrooxypropanol and derivatives thereof as well as to the production of such adsorbates.

Claims

1. A method to produce an adsorbate, said method comprising applying a mixture comprising at least one compound of formula (I) ##STR00003## wherein n is an integer from 1 to 15 R.sup.1 is selected from the group consisting of H, C.sub.1-C.sub.6alkyl, phenyl, —OH, —NH.sub.2, —CN, —COOH, —O(C═O)R.sup.8, —NHC(═O)R.sup.8, SO.sub.2NHR.sup.8, and —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 n is >3 the hydrocarbon chain may be interrupted by —O— or —NH— and a gelatin to a carrier such that the mixture is adsorbed to the carrier.

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

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

4. The method according to claim 1, wherein the mixture to be adsorbed further comprises at least one edible solvent selected from the group consisting of propylene glycol, corn oil, rapeseed oil, sunflower oil, middle chain triglyceride (MCT), water and glycerol as well as mixtures thereof.

5. The method according to claim 1, wherein the mixture to be adsorbed consists essentially of a compound of formula (I), gelatin and an edible solvent.

6. The method according to claim 1, wherein the edible solvent is propylene glycol or water.

7. The method according to claim 1, wherein the gelatin has a bloom value selected in the range of 0 to 50.

8. The method according to claim 1, wherein the carrier is silica.

9. The method according to claim 1, wherein the ratio (w/w) of the compound of formula (I) to the gelatin is selected in the range from 0.1 to 1, more preferably in the range from 0.25 to 0.8, most preferably in the range from 0.3 to 0.7.

10. An adsorbate prepared by the method according to claim 1.

11. The adsorbate according to claim 10, wherein the adsorbate comprises (i) from 1 to 25 wt-%, based on the total weight of the adsorbate, of a compound of formula (I), and (ii) from 5 to 45 wt-%, based on the total weight of the adsorbate, of at least one edible solvent, and (iii) from 5 to 25 wt.-%, based on the total weight of the adsorbate, of a gelatin, and (iv) at least 30 wt-%, based on the total weight of the adsorbate, of silica, and (v) from 0 to 10 wt-%, based on the total weight of the adsorbate, of an additive.

12. The adsorbate according to claim 10, wherein the adsorbate consists essentially of (i) 2 to 12 wt-%, based on the total weight of the adsorbate, of 3-nitrooxypropanol, and (ii) 20 to 40 wt-%, based on the total weight of the adsorbate, of propyleneglycol or water, and (iii) from 10 to 18 wt.-%, based on the total weight of the adsorbate, of a gelatin, and (vi) at least 40 wt-%, based on the total weight of the adsorbate, of precipitated silica.

13. The adsorbate according to claim 10, wherein the retention of the compound of formula (I) is at least 90%, preferably at least 93%, most preferably at least 95% after 3 months storage in a polypropylene container at 25° C. and 50% r.H.

14. An animal feed product comprising an adsorbate according to claim 10.

15. Use of gelatin in the production of an adsorbate comprising a compound of formula (I) to enhance the retention thereof upon storage.

Description

EXAMPLES

[0113] Material: Gelatin: Hydro-P and Rousselot© Pro-take™ P (from Rousselot) [0114] Silica: Sipernat 220 (from Evonik) [0115] Water: distilled water [0116] Propyleneglycol (PG): Thommen_Furlen AG [0117] 3-Nitrooxypropanol: prepared according to WO2012/084629

Preparation of a Silica/3-Nitrooxypropanol Adsorbate (Reference)

[0118] To 100 g of silica gently stirred in a beaker 100 g of solution of a 3-nitrooxypropanol (20 wt.-%) in PG was added at RT. The addition was completed after 15 min, and the free-flowing product was collected.

Preparation of a Silica/3-Nitrooxypropanol/Gelatin Adsorbate (Based on Water)

[0119] To 35 g of a solution of 3-nitrooxypropanol (20 wt.-%) in water placed in a 150 mL beaker were added 15 g of gelatin (Invention-I: Hydro-P; Invention-II: Pro-take P) (weight ratio 3-nitrooxypropanol/gelatin=0.47). The obtained solution was mixed for 45 min at RT, and afterwards added to 50 g of silica until complete adsorption. Then, the free-flowing product was collected.

Preparation of a Silica/3-Nitrooxypropanol/Gelatin Adsorbate (Based on PG)

[0120] To 35 g of a solution of 3-nitrooxypropanol (20 wt.-%) in PG placed in a 150 mL beaker were added 15 g of gelatin (Invention-III: Hydro-P; Invention IV: Pro-take P). The suspension was mixed for 45 min at RT, and afterwards added to 50 g of silica until complete adsorption. Then the free-flowing product was collected.

Stability Study:

[0121] All samples were stored on closed polypropylene (PP) tube at 25° C. and 50% r.H. For each adsorbate five samples were assessed.

[0122] The concentration of 3-nitrooxypropanol was determined by HPLC using an Agilent High Performance Liquid Chromatography 1260 Infinity system, using an Aquasil C18, 150×3 mm, 3 μm 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 set to 100%) are presented Table 1.

TABLE-US-00001 TABLE 1 Retention [%] Sample 1 week 2 weeks 3 weeks 1 months 3 months Invention-I 100 100 99.7 98.8 98.7 Invention-Ill 100 100 100 100 100 Invention-II 100 100 100 100 99.7 Invention-IV 100 100 100 100 100 Reference 96.4 96.4 92.7 96.4 94.5 (w/o gelatin)

[0123] As can be retrieved from table 1, the use of gelatin resulted in an improved retention of the active upon long time storage.