Core-shell tectodendrimers

• US 6,635,720 B1
• Filed: 01/24/2002
• Issued: 10/21/2003
• Est. Priority Date: 02/16/1999
• Status: Expired due to Fees

• Current Assignee: Dendritic NanoTechnologies, Inc. (Loveland Products, Inc.)
• Original Assignee: Dendritech Inc.
• Inventors: Swanson, Douglas R., Tomalia, Donald A., Uppuluri, Srinivas, Brothers, Herbert M. II
• Primary Examiner(s): Woodward, Ana
• Application Number:
  US09/913,050
• Time in Patent Office: 635 Days
• Field of Search: 424/DIG.16, 525/432
• US Class Current: 525/432
• CPC Class Codes: C08G 69/02 Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 69/04 Preparatory processes
• CPC Class Codes: C08G 69/48 Polymers modified by chemical after-treatment
• CPC Class Codes: C08G 83/003 Dendrimers
• CPC Class Codes: Y10S 424/16 Dendrimers and dendritic polymers
• CPC Class Codes: Y10S 977/754 Dendrimer, i.e. serially branching or "tree-like" structure
• CPC Class Codes: Y10S 977/788 Of specified organic or carbon-based composition
• CPC Class Codes: Y10S 977/835 Chemical or nuclear reactivity/stability of composition or compound forming nanomaterial

Abstract

Core-shell tecto(dendrimers) useful in biomedicine, pharmaceuticals, personal care products, and in other ways analogous to the known uses for dendrimers, hypercomb branched polymers, and other dendritic polymers are the reaction product of a core dendritic polymer molecule having a plurality of terminal functional groups of a first type which are not reactive with each other, and a plurality of shell dendritic polymer molecules having a plurality of terminal functional groups of a second type which are not reactive with each other, but which are reactive with the terminal functional groups of the first type. Each of the shell dendritic polymer molecules is chemically bonded to the core dendritic polymer molecule by a reaction of at least one of the terminal functional groups of the second type with at least one of the terminal functional groups of the first type.

Claims

1. A composition of matter comprising:

a reaction product of a core dendritic polymer molecular having a plurality of terminal functional groups of a first type which are not reactive with each other, and a plurality of shell dendritic polymer molecules having a plurality of terminal functional groups of a second type which are not reactive with each other, but which are reactive with the terminal functional groups of the first type, each of the shell dendritic polymer molecules chemically bonded to the core dendritic polymer molecule by a reaction of at least one of the terminal functional groups of the second type with at least one of the terminal functional groups of the first type, the reaction product having at least 40% of the theoretical maximum number (M_m) of dendritic polymer molecules of the second type that can be bonded to the core dendritic polymer molecule, wherein $M_m=\frac{2<br><br>\text{\hspace{1em}<br><br>}<br><br>\mathrm{\pi <br><br>}}{\sqrt{3}}<br><br>{\left(\frac{r_1}{r_2}+1\right)}^2,$

where r₁ is the radius of the core dendritic polymer molecule and r₂ is the radius of the shell dendritic polymer molecule.

4. The composition of claim 1 or 3 in which the terminal functional groups of the first type are amine groups and the terminal functional groups of the second type are methyl ester groups.

5. The composition of claim 1 or 3 in which the terminal functional groups of the first type are amine groups and the terminal functional groups of the second type are carboxylic acid functional groups.

6. The composition of claim 1 or 3 in which the core dendritic polymer molecules and the shell dendritic polymer molecules are at least third-generation dendrimers.

7. The composition of claim 1 or 3 in which the core dendritic polymer molecule is a polyamidoamine dendrimer having amine terminal groups and the shell dendritic polymer molecules are polyamidoamine dendrimers having methyl ester terminal groups or carboxylic acid terminal groups.

8. A composition of matter as claimed in claim 1 when prepared by the process as claimed in claim 2.

2. A process for preparing a composition of matter which is the reaction product of a core dendritic polymer molecule and a plurality of shell dendritic polymer molecules surrounding and chemically bonded to the core dendritic polymer molecule, comprising:

providing the core dendritic polymer molecules, the dendritic core polymer molecules each having a plurality of terminal functional groups of a first type which are not reactive with each other;

providing the shell dendritic polymer molecules, the shell dendritic polymer molecules having a plurality of terminal functional groups of a second type which are not reactive with each other, but which are reactive with the terminal functional groups of the first type;

combining the core dendritic polymer molecules with the shell dendritic polymer molecules in a solution, the amounts of the core dendritic polymer molecules and the shell dendritic polymer molecules being selected so that the ratio of shell dendritic polymer molecules to core dendritic polymer molecules is at least 4;

1; and

reacting the terminal groups of the first type with the terminal groups of the second type to form a core-shell polymer which is the reaction product of a single core dendritic polymer molecule and a plurality of shell dendritic polymer molecules that are chemically bonded to, and surround, the core dendritic polymer molecules, the number of shell dendritic polymer molecules bonded to each core dendritic polymer molecule being at least 40% of the theoretical maximum number (M_m) that can be bonded to the core dendritic polymer molecule, wherein $M_m=\frac{2<br><br>\text{\hspace{1em}<br><br>}<br><br>\mathrm{\pi <br><br>}}{\sqrt{3}}<br><br>{\left(\frac{r_1}{r_2}+1\right)}^2,$

where r₁ is the radius of the core dendritic polymer molecule and r₂ is the radius of the shell dendritic polymer molecule.

9. The process of claim 2 in which the terminal functional group of the core dendritic polymer molecule are amine-functional groups and the terminal functional groups of the shell dendritic polymer molecules are methyl ester groups or carboxylic acid groups.

10. The process of claim 2 in which the core dendritic polymer molecule is a polyamidoamine dendrimer having a amine terminal groups and the shell dendritic polymer molecules are polyamidoamine dendrimers having methyl ester terminal groups or carboxylic acid terminal groups.

3. The composition of matter comprising:

the reaction product of a single dendritic core polymer molecule, a plurality of shell dendritic polymer molecules chemically bonded to the surface of the core dendritic polymer molecule to form a first shell surrounding the core molecule, and a plurality of dendritic polymer molecules bonded to the shell dendritic polymer molecules to form a second shell surrounding the first shell.