Dendritic polyurea for solubilizing active substances of low solubility

Patent metadata

Field	Value
Publication number	US-9725554-B2
Application number	US-201013511700-A
Country	US
Kind code	B2
Filing date	Nov 23, 2010
Priority date	Nov 27, 2009
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

The present invention provides a composition comprising an amphiphile and an active ingredient whose solubility in water at 20° C. is not more than 10 g/L, wherein the amphiphile comprises a dendritic polyurea which is joined to at least one linear or comb-type polymer, and the joining is effected via a difunctional linker, if the repeat units of the linear polymer are composed of polymerized alkylene oxide. The invention also relates to an amphiphile comprising a dendritic polyurea and a process for preparing the amphiphile.

First claim

The invention claimed is:

1. A composition comprising an amphiphile and an active ingredient having a solubility in water at 20° C. of not more than 2 g/L, wherein the amphiphile comprises a dendritic polyurea which is joined to at least one linear polymer, and wherein the joining is effected by a difunctional linker,
wherein the difunctional linker is selected from the group consisting of tolylene 2,4-diisocyanate, tolylene 2,6-diisocyanate, 2,4′-diphenylmethane diisocyanate, isophorone diisocyanate, and mixtures thereof,
wherein the at least one linear polymer is a block polymer comprising polycaprolactone and polyethylene glycol, wherein the polyethylene glycol is connected to the difunctional linker via the polycaprolactone;
wherein the active ingredient is a pesticide,
wherein the molar mass M n of the at least one linear polymer is greater than 200 g/mol and less than 10,000 g/mol,
wherein the dendritic polyurea has a degree of branching per molecule of 10% to 90% and a weight-average molecular weight from 1,000 to 50,000 g/mol, and
wherein the at least one linear polymer is a polyethylene glycol monomethyl ether-block-polycaprolactone polymer.

2. The composition according to claim 1 , wherein the dendritic polyurea is a hyperbranched polyurea.

3. The composition according to claim 2 , wherein the hyperbranched polyurea is obtained by a process comprising the reaction of an at least difunctional blocked di- or polyisocyanate with at least one at least difunctional primary and/or secondary amine, with elimination of the blocking agent.

4. The composition according to claim 3 , wherein the blocking agent is a monoalcohol.

5. An amphiphile comprising a dendritic polyurea, wherein the dendritic polyurea is joined to at least one linear polymer, and wherein the joining is effected by a difunctional linker,
wherein the difunctional linker is selected from the group consisting of tolylene2,4-diisocyanate, tolylene 2,6-diisocyanate, 2,4′-diphenylmethane diisocyanate, isophorone diisocyanate, and mixtures thereof,
wherein the at least one linear polymer is a block copolymer comprising polycaprolactone and polyethylene glycol, wherein the polyethylene glycol is connected to the difunctional linker via the polycaprolactone,
wherein the molar mass Mn of the at least one linear polymer is greater than 200 g/mol and less than 10,000 g/mol,
wherein the dendritic polyurea has a degree of branching per molecule of 10% to 90% and a weight-average molecular weight from 1,000 to 50,000 g/mol, and
wherein the at least one linear polymer is a polyethylene glycol monomethyl ether-block-polvcaprolactone polymer.

6. The amphiphile according to claim 5 , wherein the dendritic polyurea is a hyperbranched polyurea.

7. The amphiphile according to claim 6 , wherein the hyperbranched polyurea is obtained by a process comprising the reaction of an at least difunctional blocked di- or polyisocyanate with at least one at least difunctional primary and/or secondary amine, with elimination of the blocking agent.

8. The amphiphile according to claim 7 , wherein said di- or polyisocyanate used is an oligo- or polyisocyanate having an average molar mass of 300 to 3000 g/mol.

9. The composition of claim 1 , wherein the active ingredient has a solubility in water at 20° C. of not more than 0.5_g/L.

10. The composition of claim 1 , wherein the difunctional linker is isophorone diisocyanate.

11. The composition of claim 1 , wherein the polyethylene glycol of the at least one linear polymer has a molar mass M n of 300 g/mol to 2000 g/mol.

Assignees

• Türk Holger
• Haberecht Monika
• Yamada Hiroe
• Bruchmann Bernd
• Schönfelder Daniel
• Ishaque Michael
• Basf Se

Inventors

• Türk Holger
• Haberecht Monika
• Yamada Hiroe
• Bruchmann Bernd
• Schönfelder Daniel
• Ishaque Michael

Classifications

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/3234 Primary

  cycloaliphatic · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/62

  Polymers of compounds having carbon-to-carbon double bonds · CPC title

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title