Patent Application
20080069892
A stirred three-necked flask apparatus is charged with 37.82 g of 1,2-propanediol, 100 g of acetone and 0.07 g of dibutyltin dilaurate, and 78.11 g of Desmodur® T 80 are added dropwise with cooling in such a way that the internal temperature climbs to 50° C. The isocyanate content is 0.23% 2.5 hours after the dropwise addition has been ended and after afterreaction at 50° C. After addition of 5 g of water and a further 30 minutes afterreaction at 50° C., the solution is free of isocyanate. 29 g of Folicur are introduced, and the acetone is removed by distillation up to an internal temperature of 160° C. The distillation residue is poured onto a Teflon sheet and, after cooling, pulverized in a Braun mixer. After screening over a mesh size of 63 μm, 98 g of product are obtained. According to particle size determination, 50% of the particles are <24 μm. The active substance content according to GLC is 20.1%.
Release of active substance:
In a sealed 500 ml Erlenmeyer flask, 50.0 mg of the powder are stirred at 20° C. in 200 ml of Cipac 500 ppm water. The amount of Folicur is 50.25 mg/l.
Samples are taken from the suspension at the times indicated hereinbelow and filtered through a 0.2 μm microfilter, and the active substance content is determined by means of HPLC.
In a stirred three-necked flask apparatus, 100 g of a polyester of phthalic acid and 1,2-ethanediol with a mean molar mass of 2000 g/mol and an OH content of 1.7% are molten and dehydrated for 30 minutes at 100° C. and 15 mbar. Thereafter, 9.2 g of Desmodur® PU 1806 (diphenylmethane diisocyanate, isomer mixture, Bayer) are added dropwise in the course of 15 minutes and the mixture is stirred for 4.5 hours at 130° C. Thereafter, the mixture is free of isocyanate according to IR spectrum. 27.3 g of imidacloprid are introduced and the internal temperature is raised to 150° C. The melt is poured onto a Teflon sheet and, when cold, pulverized in a Braun mixer and screened to give particles <125 μm. The active substance content found, determined by HPLC, is 19.4%.
Release of active substance:
In a sealed 200 ml Erlenmeyer flask, 52 mg of the powder are stirred at 25° C. in 100 ml of Cipac 500 ppm water. The amount of imidacloprid is 100 mg/Il.
Samples are taken from the suspension at the times indicated hereinbelow and filtered through a 0.2 μm microfilter, and the active substance content is determined by means of HPLC.
In a stirred three-necked flask apparatus, a prepolymer is prepared by introducing 111 g of isophorone diisocyanate and adding 35.4 g of 1,6-hexanediol portionwise at 120° C. Stirring is continued until the calculated value of 11.48% of NCO is reached, or almost reached. 10.92% of NCO were found.
36.6 g of the prepolymer are dissolved in 120 g of methylene chloride, and the solution is added dropwise with cooling at room temperature to a solution of 10.7 benzylamine and 50 g of methylene chloride. A few minutes after the dropwise addition has ended, the solution is free of NCO according to IR spectrum. 21.6 g of imidacloprid are introduced. The mixture is heated slowly to 150° C., during which process methylene chloride is removed by distillation. At 150° C., a vacuum of 15 mbar is applied. The melt is poured onto a Teflon sheet and pulverized in a Braun mixer and the powder is screened to give particles <125 μm. 30.0% of imidacloprid, as determined by HPLC, were found.
Release of active substance:
In a sealed 2 l Erlenmeyer flask, 3333 mg of the powder are stirred at 25° C. in 1000 ml of Cipac 500 ppm water. The amount of imidacloprid is 1000 mg/l.
Samples are taken from the suspension at the times indicated hereinbelow and filtered through a 0.2 μm microfilter, and the active substance content is determined by means of HPLC.
A stirred three-necked flask apparatus is charged with 11.8 g of 1,6-hexanediol and 2.16 g of benzyl alcohol, and 24.2 g of isophorone diisocyanate are added dropwise at 90° C. in the course of 35 minutes. Thereafter, the internal temperature is raised to 160° C. in the course of 2.5 hours. The product is NCO-free according to IR spectrum. 16.45 g of imidacloprid are slowly introduced into the melt. The homogeneous melt is poured onto a Teflon sheet and, when cold, conuninuted in a Braun mixer and the powder is screened to give particles <125 μm. 29.9% of imidacloprid, as determined by HPLC, were found.
Release of active substance:
In a sealed 2 l Erlenmeyer flask, 3345 mg of the powder are stirred at 25° C. in 1000 ml of Cipac 500 ppm water. The amount of imidacloprid is 1000 mg/l.
Samples are taken from the suspension at the times indicated hereinbelow and filtered through a 0.2 μm microfilter, and the active substance content is determined by means of HPLC.
A stirred three-necked flask apparatus is charged with 168 g of hexamethylene diisocyanate and 46 g of ethanol are added dropwise at 90° C. in the course of 1 hour. Then, 45 g of 1,4-butanediol are added dropwise in the course of a further hour, and the temperature is raised to 160° C. Stirring is continued at this temperature until the melt no longer contains isocyanate according to IR spectroscopy. The product is poured onto a Teflon sheet and, when cold, comminuted in a Braun mixer.
A stirred three-necked flask apparatus is charged with 35.3 g of 1,2-propanediol and 71.5 g of acetone, and 64.8 g of isomer mixture consisting to 80% of toluylene diisocyanate and to 20% of 2,6-toluylene diisocyanate are added dropwise, with cooling. Stirring is continued for 2 hours at 50° C. The isocyanate content of the clear solution is 0.1%.
In a stirred three-necked flask apparatus, 30 g of methiocarb, 20 g of polyurethane of Example 5, 85.8 g of the acetonic solution of Example 6 and 0.1 g of stearic acid are heated to 110° C., and the acetone is removed via a distillation head, first under atmospheric pressure and thereafter at up to 15 mbar. The melt is poured onto a Teflon sheet and, when cold, ground in a Braun mixer and screened to give particles <125 μm. The active substance content identified by HPLC is 26.5%.
Release of active substance:
In a sealed 500 ml Erlenmeyer flask, 0.038 g of the powder is stirred in 200 ml of buffer solution pH 4 (Riedel-de Haen, Art. No. 33543) at 25° C. The amount of methiocarb is 50 mg/l.
Samples are taken from the suspension at the points in time indicated hereinbelow and filtered through a 0.2 μm microfilter, and the active substance content is determined by means of HPLC.
| Number | Date | Country | Kind |
|---|---|---|---|
| 102004004143.1 | Jan 2004 | DE | national |
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/EP05/00474 | 1/19/2005 | WO | 00 | 4/26/2007 |
