Polymer micelles containing nanoparticles in non-aqueous solution, methods for their preparation and use

Patent metadata

Field	Value
Publication number	US-10357751-B2
Application number	US-201515519130-A
Country	US
Kind code	B2
Filing date	Oct 13, 2015
Priority date	Oct 13, 2014
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

The present invention relates to a composition, comprising at least one micelle in non-aqueous solution, wherein the micelle encapsules one or more nanoparticle(s) and wherein the micelle comprises a cross-linked hydrophilic shell.
Furthermore, the present invention relates to the use of such a composition and to methods for providing such a composition.

First claim

The invention claimed is:

1. A method, comprising: providing a composition comprising at least one micelle encapsulating one or more nanoparticle(s) in a non-aqueous solution, wherein the micelle comprises a cross-linked hydrophilic shell, wherein the cross-linking of the micelle is enabled using thiol-ene click chemistry, and wherein the encapsulation and cross-linking are performed under completely anhydrous conditions.

2. The method according to claim 1 , wherein the one or more nanoparticle(s) is a luminescent nanoparticle.

3. The method according to claim 2 , wherein the one or more nanoparticle(s) is a semi-conductor nanoparticle.

4. The method according to claim 3 , wherein the one or more nanoparticle(s) is doped by heavy-metal ions including Ag, Cu, Co, or Mn.

5. The method according to claim 2 , wherein the one or more nanoparticle(s) is chosen from a lattice lanthanide doped nanoparticle.

6. The method according to claim 1 , wherein the one or more nanoparticle(s) is a metal nanoparticle or a metal oxide nanoparticle.

7. The method according to claim 1 , wherein a material of the one or more nanoparticle(s) is defined by a formula M w N x A y B z , wherein M and N are independently selected from elements from group 8, 9, 10, 11, 12, 13, or 14 of the periodic table, including Fe, Co, Ni, Pt, Cu, Zn, Cd, Al, Ga, In, Ge, Sn, or Pb, and A and B are independently selected from elements from group 10, 11, 13, 15, or 16 from the periodic table, including Pd, Pt, N, P, As, Sb, Ga, O, S, Se, or Te, and wherein w, x, y, and z can be independently varied between 0 and 1 and their integral multiples under a proviso that positive charges of the cationic elements equal negative charges of the anionic elements.

8. The method according to claim 1 , wherein the one or more nanoparticle(s) comprises at least one shell.

9. The method according to claim 8 , wherein a material of the at least one shell is defined by the formula O s C t D u , wherein 0 can be independently chosen from group 8, 9, 10, 11, 12, 13, or 14 from the periodic table, including Fe, Co, Ni, Pt, Cu, Zn, Cd, Al, Ga, In, Ge, Sn, or Pb, and C and D can be independently chosen from group 10, 11, 15, or 16 from the periodic table, including Pd, Pt, N, P, As, Sb, 0, S, Se, or Te, and wherein s, t, and u can be independently varied between 0 and 1 and their integral multiples under a proviso that positive charges of the cationic elements equal negative charges of the anionic elements and under a proviso that the compositions of M w N x A y B z and O s C t D u are not identical.

10. The method according to claim 1 , wherein the at least one micelle comprises micelle forming elements including amphiphilic block co-polymers.

11. The method according to claim 10 , wherein the amphiphilic block co-polymers comprise at least two different polymer blocks of different compatibility towards solvents.

12. The method according to claim 11 , wherein the amphiphilic block co-polymers are linear or branched or star-shaped or dendritic.

13. The method according to claim 1 , wherein the at least one micelle is formed in the non-aqueous solution and the non-aqueous solution is chosen from at least one of:
unbranched, branched, or cyclic alkanes, optionally bearing one or more halogen atoms, including pentane, hexane, iso-hexanes, cyclopentane, cyclohexane, dichloromethane, chloroform, 1,1-dichloroethane, or 1,2-dichloroethane;
halogenated alkenes, like 1,1-dichloroethene or all isomers of 1,2-dichloroethene; optionally alkylated aromatic or heteroaromatic solvents, optionally bearing one or more halogen atoms, including benzene, toluene, ethyl benzene, xylenes, chloro benzene, pyridine, collidines, or lutidines;
unbranched, branched, or cyclic ethers, including diethyl ether, diisopropyl ether, methyl t-butyl ether, tetrahydrofuran, or 1,4-dioxane;
carbonyl compounds, including acetone, methyl ethyl ketone, cylopentanone, or cyclohexanone;
carboxylic acid esters, including ethyl acetate, unbranched or branched C 1 -C 5 alkanols, including methanol, ethanol, n-propanol, i-propanol, or all isomers of butanol and pentanol;
polyols, including ethylene glycol, 1,2-propanediol, 1,3-propanediol, glycerol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2,4-butanetriol, diethylene glycol (DEG);
ethers of polyols, including 2-methoxyethanol, bis-(2-methoxyethyl) ether (diglyme);
esters of polyols, including diacetoxyethane;
carboxylic acids, including formic acid, acetic acid, propanoic acid, lactic acid;
dialkyl sulfoxides, including dimethyl sulfoxide (DMSO);
carboxylic acid amides, including formamide, acetamide, N-methyl formamide, N-methyl acetamide, N,N-dimethyl formamide (DMF), N,N-dimethyl acetamide (DMA), or N-methyl pyrrolidone (NMP);
phosphoric acid amides including hexamethyl phosphoric acid triamide (HMPA);
urea based solvents including 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), 1,3-dimethyl-2-imidazolidinone (DMI), tetramethyl urea (TEMUR); or lower alkylnitriles including acetonitrile, propionitrile, or butyronitrile;
ionic liquids, including ammonium-based ionic liquids;
imidazolium based ionic liquids including 1-allyl-3-methylimidazolium, 1-benzyl-3-methylimidazolium, 1-butyl-2,3-dimethylimidazolium, 1-butyl-3-methylimidazolium, 1-decyl-3-methylimidazolium, 1,3-didecyl-2-methylimidazolium, 1,3-dimethylimidazolium, 1,2-dimethyl-3-propylimidazolium, 1-dodecyl-3-methylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1-ethyl-3-methylimidazolium, 1-hexadecyl-3-methylimidazolium, 1-hexyl-3-methylimidazolium, 1-(2-hydroxyethyl)-3-methylimidazolium, 1-methyl-3-octadecylimidazolium, 1-methyl-3-octylimidazolium, salts of 1-methyl-3-propylimidazolium with complex anions including tetrafluoroborate; piperidinium-based ionic liquids, including 1-butyl-1-methylpiperidinium, or 1-methyl-1-propylpiperidinium;
pyridinium-based ionic liquids including 1-alkyl-2-methylpyridinium, 1-alkyl-3-methylpyridinium, 1-alkyl-4-methylpyridinium, 1-butylpyridinium, 1-propylpyridinium, 1-ethylpyridinium, salts of 1-hexylpyridinium salts with complex anions including tetrafluoroborate;
pyrrolidinium-based ionic liquids, including 1-butyl-1-methylpyrrolidinium, 1-ethyl-1-methylpyrrolidinium, salts of 1-methyl-1-propylpyrrolidinium with complex anions, and combinations or combinations of mixtures thereof.

14. The method according to claim 1 , wherein the non-aqueous solution comprises one or more of a water miscible non-aqueous solvent and a non-aqueous solvent, which does not form azeotropic phases with water.

15. The method according to claim 14 , wherein the water miscible non-aqueous solvent has a higher boiling point than water.

Assignees

• Fraunhofer Ges Forschung

Inventors

• Schotten Theo
• Werner Katja
• Ott Carsten
• Niehaus Jan Steffen
• Dieckmann Marieke
• Weller Horst
• Ostermann Johannes
• Hahn Christoph

Classifications

• C08K2003/0843

  Cobalt · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• B82Y5/00

  Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery · CPC title

• G01N33/5432

  Liposomes or microcapsules · CPC title

• C08K2003/085

  Copper · CPC title