# US 2017/0283548 A1 · Poly (e-caprolactone)-ethoxylated fatty alcohol copolymers

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- Number: US 2017/0283548 A1
- Document ID: US20170283548A1
- Status: Published application
- Kind: A1
- Application number: 15/084,441
- Filed: 2016-03-29
- Published: 2017-10-05
- Earliest claimed: 2016-03-29
- Assignees: King Saud University
- Applicants: King Saud University
- Inventors: ZIYAD BINKHATHLAN; ABDULLAH H. ALOMRANI; AWS ALSHAMSAN; IBRAHIM I. ALJUFFALI; RAISUDDIN ALI
- Web page: https://patentgrep.com/patent/US20170283548A1

## CPC

- C08G 63/823: {for the preparation of polylactones or polylactides}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 9/5146: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides}
- A61K 9/5153: {Polyesters, e.g. poly(lactide-co-glycolide)}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- C08G 63/08: Lactones or lactides
- C08G 63/912: {derived from hydroxycarboxylic acids}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The poly(ε-caprolactone)-ethoxylated fatty acid copolymers are block copolymers including ε-caprolactone units and ethoxylated fatty alcohol units, the block copolymer having the structural formula: where n and m are integers greater than 0 and R is an alkyl group. The block copolymer is prepared by polymerizing ε-caprolactone and an ethoxylated fatty alcohol in the presence of a catalyst, such as stannous octoate. The block copolymers have potential as delivery systems for various payloads, such as, but not limited to, lipid soluble drugs and diagnostic agents.

## Claims

### Claim 1 (depends on 1)

A poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer, comprising a block copolymer having at least one ε-caprolactone unit and ethoxylated fatty alcohol units, the block copolymer having the structural formula:
where n and m are integers greater than 0 and R is an alkyl group, and
wherein the poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer of claim 1, wherein n is 1 to 100, m is 10 to 100, and R is an alkyl group having 12-18 carbon atoms.

### Claim at position 2

2-3. (canceled)

### Claim 4 (depends on 1)

The poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer of claim 1, wherein the block copolymer has an average molecular weight of at least 3000 Daltons.

### Claim 5

A method of making a poly(s-caprolactone)-ethoxylated fatty alcohol copolymer, comprising the steps of:
mixing ε-caprolactone and an ethoxylated fatty alcohol in a reaction vessel to form a reaction mixture;
adding a catalyst to the reaction mixture to catalyze polymerization; and
heating the reaction vessel to 140° C.

### Claim 6 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, wherein said step of heating the reaction vessel to 140° C. comprises polymerizing the reaction mixture at a temperature of about 140° C. for between 4-5 hours.

### Claim 7 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, further comprising the steps of:
purging the reaction vessel of nitrogen;
sealing the reaction vessel; and
polymerizing the reaction mixture under vacuum.

### Claim 8 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, wherein said catalyst comprises stannous octoate.

### Claim 9 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, wherein said catalyst comprises bidentate sulfonamide zinc complex.

### Claim 10 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, wherein the ethoxylated fatty alcohol has a molecular weight between 1000 and 50,000 Daltons.

### Claim 11 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, further comprising the step of cooling the reaction vessel to room temperature to terminate polymerization.

### Claim 12 (depends on 5)

The method of making a poly(ε-caprolactone)-ethoxylated fatty alcohol copolymer according to claim 5, wherein the ethoxylated fatty alcohol comprises polyoxyethylene stearyl ether.

### Claim 13

(canceled)

### Claim 14

A method of preparing self-assembled nanocarriers, comprising the steps of:
dissolving a poly(ε-caprolactone)-ethoxylated fatty alcohol block copolymer in an organic solvent to form a solution;
adding the solution drop-wise into distilled water; and
evaporating the organic solvent to form self-assembled nanocarriers.

### Claim 15 (depends on 14)

The method of preparing self-assembled nanocarriers according to claim 14, wherein the self-assembled nanocarriers have a mean diameter between 50 nm and 300 nm.

### Claim 16 (depends on 14)

The method of preparing self-assembled nanocarriers according to claim 14, wherein the organic solvent comprises at least one solvent selected from the group consisting of acetone, tetrahydrofuran, acetonitrile, and dimethyl oxide.
