# US 2020/0087464 A1 · Preparation of solvent and polymer redispersible formulations of dried cellulose nanocrystals (cnc)

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- Number: US 2020/0087464 A1
- Document ID: US20200087464A1
- Status: Published application
- Kind: A1
- Application number: 16/613,995
- Filed: 2018-05-15
- Published: 2020-03-19
- Earliest claimed: 2017-05-19
- Assignees: Celluforce Inc.
- Applicants: Celluforce Inc.
- Inventors: Philippe BOURASSA; Myriam METHOT; Richard BERRY
- Web page: https://patentgrep.com/patent/US20200087464A1

## CPC

- C08J 3/092: {Hydrocarbons}
- C30B 29/58: Macromolecular compounds
- C08B 15/00: Preparation of other cellulose derivatives or modified cellulose {, e.g. complexes}
- C08J 3/095: {Oxygen containing compounds}
- C08J 3/12: Powdering or granulating
- C08J 5/005: {Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials}
- C08L 1/02: Cellulose; Modified cellulose
- C30B 7/14: the crystallising materials being formed by chemical reactions in the solution
- C30B 29/54: Organic compounds
- C08J 2301/02: Cellulose; Modified cellulose
- C08J 2325/06: Polystyrene
- C08J 2367/04: Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence)
- C08J 2371/02: Polyalkylene oxides
- C08J 2425/06: Polystyrene
- C08J 2467/04: Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2467/06 takes precedence)
- 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)
- C30B: SINGLE-CRYSTAL GROWTH (by using ultra-high pressure, e.g. for the formation of diamonds, B01J3/06); UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL (zone-refining of metals or alloys C22B); PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (casting of metals, casting of other substances by the same processes or devices B22D; working of plastics B29; modifying the physical structure of metals or alloys C21D, C22F); SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (for producing semiconductor devices or parts thereof H10); APPARATUS THEREFOR
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The disclosure provides redispersible CNC. The CNC disclosed herein is redispersible in non-polar and polar organic solvents as well as polar and non-polar polymers such as polyethylene or polypropylene. The disclosure surprisingly also provides redispersible CNC bearing improved redispersion in aqueous systems and most particularly in high ionic strength aqueous systems which usually require significant mixing energy to achieve dispersion.

## Claims

### Claim 1

A redispersible cellulose nanocrystal (CNC) wherein said CNC is comprising non-covalent ionic adduct of a cationic groups formed from a protonated amine compound and anionic groups formed from titrable acidic groups, wherein said titrable acidic groups are located at the surface of said CNC, wherein said titrable acid group is comprising sulfate or phosphate half-esters, carboxylic acids or mixtures thereof, and wherein said redispersible CNC is in an isolated dried form.

### Claim 2 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said titrable acid group is comprising sulfate half-esters (unmodified or desulfated), carboxylic acids or mixtures thereof.

### Claim 3 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said amine compound is an amine-terminated polyalkane, an amine-terminated polyalkylether or an amine-terminated polyalkylene imine.

### Claim 4 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said amine compound is a monoamine-terminated polyalkane, a monoamine-terminated polyalkylether or a monoamine-terminated polyalkylene imine.

### Claim 5 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said amine compound is monoamine-terminated polyalkylether having the formula:
R1—[O(CH2)x]a—[OCH2CH(CH3)]b—NH2
wherein said polyalkylether may be a homopolymer, an AB or ABA block copolymer, or an alternating copolymer;
R1 is H, or selected from an optionally substituted, linear or branched alkyl of 1 to 14 carbon atoms; or R1 is an optionally substituted aryl of 6 to 10 carbon atoms; or R1 is an alkyl-arylene-group wherein each of said alkyl and arylene residues are independently optionally substituted and further said alkyl residue is linear or branched alkyl of 1 to 14 carbon atoms and said arylene residue is comprising 6 to 10 carbon atoms;
a or b are each independently an integer from 1 to 60, wherein optionally one of said a or b may be zero (0) in the case of an homopolymer;
x is an integer from 1 to 4.

### Claim 6 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said amine compound is an amine-terminated polyalkylether having the formula:
wherein a and b a or b are each independently an integer from 1 to 60, wherein optionally one of said a or b may be zero (0) in the case of an homopolymer,
R2 at each occurrence of monomer b can be R2═H for ethylene oxide (EO) or R2═CH3 for propylene oxide (PO).

### Claim 7 (depends on 6)

The redispersible CNC as defined in claim 6, wherein the polyethylene/polypropylene oxide (PO/EO) ratio is from 1/10 to 10/1.

### Claim 8 (depends on 1)

The redispersible CNC as defined in claim 1, wherein said amine compound has a molecular weight from 300 and 5000 g/mol.

### Claim 9 (depends on 1)

The redispersible CNC as defined in claim 1, which is in a pelletized or molded form.

### Claim 10

A method for producing an isolated dried redispersible cellulose nanocrystal (CNC) comprising
i) providing an aqueous suspension of an acidic CNC;
ii) mixing an amount of an amine compound with said suspension of an acidic CNC, wherein said amount is sufficient to cause the pH of said suspension to increase to about below the pKa of the protonated amine compound; and
iii) drying the suspension resulting from step ii to produce said redispersible CNC.

### Claim 11 (depends on 10)

The method of claim 10, wherein the molar ratio of said amine compound to titrable acid groups in the acidic CNC is about 1:1.

### Claim 12 (depends on 10)

The method of claim 10, wherein the molar ratio of said amine compound to titrable acid groups in the acidic CNC is such that said pH of the suspension is between about 3 and 10 the final pH of the suspension is about neutral.

### Claim 13 (depends on 12)

The method of claim 12, wherein said pH of the suspension is about 7.

### Claim 14 (depends on 10)

The method of claim 10, wherein said amine compound is monoamine-terminated polyalkylether having the formula:
R1—[O(CH2)x]a—[OCH2CH(CH3)]b—NH2
wherein said polyalkylether may be a homopolymer, an AB or ABA block copolymer, or an alternating copolymer;
R1 is H, or selected from an optionally substituted, linear or branched alkyl of 1 to 14 carbon atoms; or R1 is an optionally substituted aryl of 6 to 10 carbon atoms; or R1 is an alkyl-arylene- group wherein each of said alkyl and arylene residues are independently optionally substituted and further said alkyl residue is linear or branched alkyl of 1 to 14 carbon atoms and said arylene residue is comprising 6 to 10 carbon atoms;
a or b are each independently an integer from 1 to 60, wherein optionally one of said a or b may be zero (0) in the case of an homopolymer;
x is an integer from 1 to 4.

### Claim 15 (depends on 10)

The method of claim 10, wherein said amine compound is an amine-terminated polyalkylether having the formula:
wherein a and b a or b are each independently an integer from 1 to 60, wherein optionally one of said a or b may be zero (0) in the case of an homopolymer,
R2 at each occurrence of monomer b is independently R2═H for ethylene oxide (EO) or R2═CH3 for propylene oxide (PO).

### Claim 16 (depends on 1)

A polymer composite comprising a redispersible CNC as defined in claim 1.