# US 10,307,486 B2 · Surface modified nanocrystalline cellulose and uses thereof

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- Number: US 10,307,486 B2
- Document ID: US10307486B2
- Status: Granted
- Kind: B2
- Application number: 15/245,883
- Filed: 2016-08-24
- Published: 2017-05-11
- Granted: 2019-06-04
- Earliest claimed: 2012-08-03
- Assignees: Celluforce Inc.
- Applicants: Celluforce Inc.
- Inventors: Seyedeh Parinaz Akhlaghi; Kam Chiu Tam; Richard M. Berry
- Web page: https://patentgrep.com/patent/US10307486B2

## CPC

- A61K 47/38: Cellulose; Derivatives thereof
- A23L 29/262: Cellulose; Derivatives thereof, e.g. ethers
- A23L 29/281: Proteins, e.g. gelatin or collagen
- A61K 8/731: {Cellulose; Quaternized cellulose derivatives}
- A61K 8/736: {Chitin; Chitosan; Derivatives thereof}
- A61K 9/5161: {Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin}
- A61K 31/245: Amino benzoic acid types, e.g. procaine, novocaine (salicylic acid esters A61K31/60)
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61Q 17/005: {Antimicrobial preparations}
- A61Q 19/00: Preparations for care of the skin
- C08B 15/00: Preparation of other cellulose derivatives or modified cellulose {, e.g. complexes}
- C08B 15/04: Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide
- C08B 15/06: containing nitrogen {, e.g. carbamates}
- C08B 37/003: {Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof}
- A61K 2800/413: Nanosized, i.e. having sizes below 100 nm
- A61K 2800/57: Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
- A61K 2800/612: By organic compounds
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)

## Abstract

The present disclosure relates to surface modified nanocrystalline cellulose (NCC) prepared by chemical modification of NCC as well as its use thereof, including as carrier of particular chemical compounds. The surface of nanocrystalline cellulose (NCC) was modified with chitosan oligosaccharide (CSOS) by selectively oxidizing the primary alcohol moieties of NCC followed by coupling of the amino groups of CSOS to the oxidized NCC to provide the desired material (NCC-CSOS).

## Claims

### Claim 1

A surface modified nanocrystalline cellulose (NCC) comprising chitosan oligosaccharides (CSOS) covalently bond to the external surface of said NCC (NCC-CSOS).

### Claim 2 (depends on 1)

The modified nanocrystalline cellulose (NCC) of claim 1, wherein said covalent bond is a peptide bond.

### Claim 3 (depends on 1)

The modified nanocrystalline cellulose (NCC) of claim 1, wherein said covalent bond is an imine (C═N).

### Claim 4 (depends on 1)

A pharmaceutically, cosmetically or agriculturally active agent comprising the NCC-CSOS as defined in claim 1 and a pharmaceutically, cosmetically or agriculturally active chemical compound loaded on said NCC-CSOS.

### Claim 5 (depends on 4)

A pharmaceutical, cosmetical or agricultural composition comprising the pharmaceutically, cosmetically or agriculturally active agent as defined in claim 4 admixed together with one or more acceptable carriers, excipients or diluents.

### Claim 6

A method for preparing a surface modified nanocrystalline cellulose (NCC) comprising oxidizing primary hydroxyl groups of said NCC to provide oxidized functional groups and covalently bonding chitosan oligosaccharides (CSOS) to the oxidized functional groups.

### Claim 7 (depends on 6)

The method of claim 6, wherein said primary hydroxyl is oxidized to a carboxyl functional group.

### Claim 8 (depends on 7)

The method of claim 7, wherein said primary hydroxyl is oxidized by TEMPO-mediated oxidation sodium or potassium dichromate (VI) acidified with dilute sulphuric acid or ammonium persulfate.

### Claim 9 (depends on 7)

The method of claim 7, wherein said covalent bond is obtained by contacting said oxidized primary hydroxyl groups of NCC and said chitosan oligosaccharides (CSOS) with a carbodiimide reagent.

### Claim 10 (depends on 8)

The method of claim 8, wherein said covalent bond is obtained by contacting said oxidized primary hydroxyl groups of NCC and said chitosan oligosaccharides (CSOS) with a carbodiimide reagent.

### Claim 11 (depends on 6)

The method of claim 6, wherein said primary hydroxyl is oxidized to an aldehyde functional group.