CONVENIENT SYNTHESIS OF 1 --> 3 C-BRANCHED DENDRONS

• US 20100041859A1
• Filed: 11/11/2005
• Published: 02/18/2010
• Est. Priority Date: 11/11/2004
• Status: Active Grant

• Current Assignee: University of Akron
• Original Assignee: University of Akron
• Inventors: Kotta, Kishore K., Moorefield, Charles N., Newkome, George R.
• Granted Patent: US 8,138,301 B2
• Time in Patent Office: Days
• US Class Current: 528/332
• CPC Class Codes: C07C 265/14 containing at least two isocyanate groups bound to the same carbon skeleton
• CPC Class Codes: C08G 73/028 Polyamidoamines
• CPC Class Codes: C08G 83/003 Dendrimers
• CPC Class Codes: C08L 101/005 Dendritic macromolecules

Abstract

In accordance with the present invention, there is provided a method of preparing higher generation 1→3 C-branched polyamide dendrons. The combination of commercially available acryloyl chloride with 1→3 C-branched amines, e.g., di-tert-butyl 4-[2-(tert-butoxycarbonyl)ethyl]-4-aminoheptanedioate, resulted in generally high yields of acryl amides, which upon treatment with other reagents, generated the desired higher generation dendrons. These second and third generation dendrons were fully characterized and compared to the samples prepared from a convergent synthesis.

Claims

1. A method of preparing a 1→

3 C-branched dendrimer, the method comprising the steps of;

reacting an amine with at least acryloyl chloride to form a N-substituted amide;

reacting the N-substituted amide with at least nitromethane to form a second amide;

reacting the N-substituted amide and the second amide at a predetermined ratio to form a predendron;

hydrogenating the predendron in the presence of a catalyst to form an amine dendron; and

reacting the amine dendron with at least an amount of triphosgene to form an isocyanate dendron.

2. The method of claim 1 further comprising the steps of:

reacting second amide with at least an amount of acryloyl chloride to form a third amide;

reacting the third amide with at least an amount of nitromethane to form a third generation predendron;

hydrogenating the predendron in the presence of a catalyst to form a third generation dendron; and

reacting the third generation dendron with at least an amount of triphosgene to form a third generation isocyanate dendron.

3. The method of claim 1, wherein the predendron is a second generation predendron.

4. The method of claim 1, wherein the catalyst is a Raney-Nickel catalyst.

5. The method of claim 1, wherein the amine dendron is a second generation dendron.

6. The method of claim 1, wherein the third amide is a second generation acryl amide.

7. The method of claim 1, wherein the predetermined ratio of the N-substituted amide:

second amide is approximately 2;

1.

8. A dendrimer comprising:

a plurality of dendrons emanating from a common core, wherein the dendrimer is devoid of dicyclohexyl urea as a by-product.

9. The dendrimer of claim 8, wherein the dendrimer is a second generation isocyanate.

10. The dendrimer of claim 8, wherein the dendrimer is a third generation isocyanate.