# US 10,245,230 B2 · Method for incorporating active agents into a hydrophilic polymer foam

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,245,230 B2
- Document ID: US10245230B2
- Status: Granted
- Kind: B2
- Application number: 15/647,992
- Filed: 2017-07-12
- Published: 2017-10-26
- Granted: 2019-04-02
- Earliest claimed: 2012-12-18
- Assignees: Laboratoires Urgo
- Applicants: Laboratoires Urgo
- Inventors: Jean-Marc Henri Maurice Pernot; Anne-Laure Ravenet
- Web page: https://patentgrep.com/patent/US10245230B2

## CPC

- A61K 9/122: {Foams; Dry foams (edible foams A61K9/0056)}
- A61F 13/00991: {for treating webs, e.g. for moisturising, coating, impregnating or applying powder}
- A61F 13/84: Accessories, not otherwise provided for, for absorbent pads
- A61K 8/046: {Aerosols; Foams}
- A61K 8/87: Polyurethanes
- A61K 31/17: having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine (isoureas, isothioureas A61K31/155; sulfonylureas A61K31/64)
- A61K 31/7016: Disaccharides, e.g. lactose, lactulose (lactobionic acid A61K31/7032)
- 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)
- A61L 15/44: Medicaments
- A61P 17/12: Keratolytics, e.g. wart or anti-corn preparations
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- A61P 31/12: Antivirals
- A61P 37/02: Immunomodulators
- B29C 44/12: Incorporating or moulding on preformed parts, e.g. inserts or reinforcements
- C08J 9/28: by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
- A61K 2800/10: General cosmetic use
- A61K 2800/56: Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
- C08J 2201/0504: the liquid phase being aqueous
- C08J 2207/10: Medical applications, e.g. biocompatible scaffolds
- C08J 2375/04: Polyurethanes
- 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)
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

The present invention consists of a novel process for the incorporation of one or more water-soluble active agents in a hydrophilic polymer foam. Said process makes it possible in particular to obtain a hydrophilic polyurethane foam exhibiting a gradient of active agents. This process is of particular use when manufacturing hydrophilic polyurethane foams intended for medical, cosmetic and dermocosmetic purposes.

## Claims

### Claim 1

A process for manufacturing a hydrophilic polymer foam exhibiting a gradient of a water-soluble active agent, the process comprising:
a) depositing an aqueous solution or dispersion comprising the water-soluble active agent on an impermeable nonporous support;
b) pouring a precursor mixture of the foam, in a form of an aqueous dispersion comprising either monomers or prepolymers, over the aqueous solution or dispersion that has been deposited on the support at the end of step a), wherein the aqueous solution or dispersion that has been deposited on the support at the end of step a) dissolves in the precursor mixture of the foam;
c) polymerizing the precursor mixture in which the water-soluble active agent is dissolved in step b) to produce the hydrophilic polymer foam incorporating the water-soluble active agent;
d) drying the hydrophilic polymer foam; and
e) separating the impermeable nonporous support from the foam after the foam has been dried in step d),
wherein 80% -90% of the total weight of the water-soluble active agent is found in the lower 33% of the total volume of the hydrophilic polymer foam, which is the volume of the foam closest to the impermeable nonporous support at the end of step d).

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the foam is a hydrophilic polyurethane foam which is obtained with a precursor mixture comprising a prepolymer of poly(alkyleneoxy) polyol type.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein the precursor mixture of the foam comprises a silicone-based surfactant.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein the precursor mixture of the foam comprises a nonionic surfactant.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein the water-soluble active agent is chosen from the group consisting of antibacterial agents, anti-inflammatory agents, keratolytic agents, immunomodulating agents, chelating agents, pH-modifying agents, compounds of the extracellular matrix, agents which promote healing, antiviral agents, antifungal agents and painkillers.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the water-soluble active agent is urea or hyaluronic acid.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein the aqueous solution or dispersion of the water-soluble active agent is deposited on the support by spraying.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein the impermeable nonporous support is a silicone-treated support.

### Claim 9 (depends on 1)

The process as claimed in claim 1, wherein the water-soluble active agent is a synthetic polysulfated oligosaccharide having from 1 to 4 monosaccharide units, a salt of said polysulfated oligosaccharide, or a complex of polysulfated oligosaccharide.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein 90% of the total weight of the water-soluble active agent introduced in the process for the manufacture of the hydrophilic polymer foam is found in the lower 33% of the hydrophilic polymer foam.

### Claim 11 (depends on 1)

The process as claimed in claim 1, wherein the impermeable nonporous support is a silicone-treated polyethylene-coated paper or a silicone-treated polyester film.

### Claim 12

A process for manufacturing a hydrophilic polymer foam exhibiting a gradient of a water-soluble active agent, the process comprising:
a) depositing an aqueous solution or dispersion comprising the water-soluble active agent on an impermeable nonporous support, and drying the support on which the aqueous dispersion or solution has been deposited to obtain a support that is coated with the water-soluble active agent;
b) pouring a precursor mixture of the foam, in a form of an aqueous dispersion comprising either monomers or prepolymers, over the support that has been obtained at the end of step a), wherein the water-soluble active agent dissolves in the aqueous dispersion comprising the precursor mixture of the foam;
c) polymerizing the precursor mixture in which the water-soluble active agent is dissolved in step b) to produce the hydrophilic polymer foam incorporating the water-soluble active agent;
d) drying the hydrophilic polymer foam; and
e) separating the impermeable nonporous support from the foam after the foam has been dried in step d),
wherein 80% -90% of the total weight of the water-soluble active agent is found in the lower 33% of the total volume of the hydrophilic polymer foam, which is the volume of the foam closest to the impermeable nonporous support at the end of step d).

### Claim 13 (depends on 12)

The process as claimed in claim 12, wherein the foam is a hydrophilic polyurethane foam which is obtained with a precursor mixture comprising a prepolymer of poly(alkyleneoxy) polyol type.

### Claim 14 (depends on 12)

The process as claimed in claim 12, wherein the precursor mixture of the foam comprises a silicone-based surfactant.

### Claim 15 (depends on 12)

The process as claimed in claim 12, wherein the precursor mixture of the foam comprises a nonionic surfactant.

### Claim 16 (depends on 12)

The process as claimed in claim 12, wherein the water-soluble active agent is chosen from the group consisting of antibacterial agents, anti-inflammatory agents, keratolytic agents, immunomodulating agents, chelating agents, pH-modifying agents, compounds of the extracellular matrix, agents which promote healing, antiviral agents, antifungal agents and painkillers.

### Claim 17 (depends on 12)

The process as claimed in claim 12, wherein the water-soluble active agent is urea or hyaluronic acid.

### Claim 18 (depends on 12)

The process as claimed in claim 12, wherein the aqueous solution or dispersion of the water-soluble active agent is deposited on the support by spraying.

### Claim 19 (depends on 12)

The process as claimed in claim 12, wherein the impermeable nonporous support is a silicone-treated support.

### Claim 20 (depends on 12)

The process as claimed in claim 12, wherein the water-soluble active agent is a synthetic polysulfated oligosaccharide having from 1 to 4 monosaccharide units, a salt of said polysulfated oligosaccharide, or a complex of polysulfated oligosaccharide.

### Claim 21 (depends on 12)

The process as claimed in claim 12, wherein 90% of the total weight of the water-soluble active agent introduced in the process for the manufacture of the hydrophilic polymer foam is found in the lower 33% of the hydrophilic polymer foam.

### Claim 22 (depends on 12)

The process as claimed in claim 12, wherein the impermeable nonporous support is a silicone-treated polyethylene-coated paper or a silicone-treated polyester film.