Sulfate ester modified cellulose nanofibers and method for producing cellulose nanofibers

Patent metadata

Field	Value
Publication number	US-12084525-B2
Application number	US-202217956990-A
Country	US
Kind code	B2
Filing date	Sep 30, 2022
Priority date	Jan 16, 2017
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

Sulfate ester modified cellulose nanofibers having an average fiber diameter in the range of 1 nm to 500 nm, and having sulfate ester modified hydroxyl groups on surfaces of the cellulose nanofibers. A method of producing cellulose nanofibers that are nanosized, that have a high crystallinity degree, and that have large aspect ratios, the method being a chemical method that does not require any physical pulverization, that is energy-saving, and that can be performed under mild reaction conditions. A method of producing modified cellulose nanofibers including modifying the surfaces of the cellulose nanofibers through esterification or urethanization. A method of producing cellulose nanofibers includes impregnating cellulose with a fibrillation solution containing dimethylsulfoxide, at least one carboxylic acid anhydride selected from acetic anhydride and propionic anhydride, and sulfuric acid to fibrillate the cellulose.

First claim

The invention claimed is:

1. A method of producing cellulose nanofibers, comprising
preparing a fibrillation solution containing dimethylsulfoxide, at least one carboxylic acid anhydride selected from acetic anhydride and propionic anhydride, and sulfuric acid,
impregnating cellulose with the fibrillation solution to fibrillate the cellulose, and
subjecting hydroxyl groups on surfaces of the cellulose to sulfuric acid esterification modification,
wherein the cellulose nanofibers comprise cellulose nanofibers having sulfate ester modified hydroxyl groups on surfaces of the cellulose nanofibers.

2. The method of producing cellulose nanofibers according to claim 1 , wherein a weight ratio between the cellulose and the fibrillation solution is from 0.5/99.5 to 50/50 in terms of former/latter ratio.

3. The method of producing cellulose nanofibers according to claim 1 , wherein a concentration of the sulfuric acid in the fibrillation solution is from 0.05 wt % to 15 wt %.

4. The method of producing cellulose nanofibers according to claim 1 , wherein a concentration of the carboxylic acid anhydride in the fibrillation solution is from 0.5 wt % to 90 wt %.

5. A method of producing modified cellulose nanofibers, comprising the steps of:
producing cellulose nanofibers by the method of claim 1 ; and
reacting the resulted cellulose nanofibers to further react with an esterification modification agent or a urethanization modification agent to modify surfaces of the cellulose nanofibers.

6. The method of producing modified cellulose nanofibers according to claim 5 , wherein a concentration of sulfuric acid in a fibrillation solution to be used in the step of producing the cellulose nanofibers is from 0.05 wt % to 5 wt %.

7. The method of producing modified cellulose nanofibers according to claim 5 , wherein the esterification modification agent comprises at least one kind selected from a carboxylic acid anhydride, a vinyl carboxylate, a carboxylic acid halide, and a carboxylic acid.

8. The method of producing modified cellulose nanofibers according to claim 5 , wherein the urethanization modification agent comprises an isocyanate.

9. The method of producing cellulose nanofibers according to claim 2 , wherein a concentration of the carboxylic acid anhydride in the fibrillation solution is from 0.5 wt % to 90 wt %.

Assignees

• Yokogawa Electric Corp

Inventors

• Lin Lianzhen
• Hori Masanori
• Maruta Ayako

Classifications

• C08B15/00

  Preparation of other cellulose derivatives or modified cellulose {, e.g. complexes} · CPC title

• C08B7/00 Primary

  Preparation of cellulose esters of both organic and inorganic acids {(rendering cellulose suitable for esterification C08B1/02)} · CPC title

• Y02P20/54

  using solvents, e.g. supercritical solvents or ionic liquids · CPC title

• C08L1/12

  Cellulose acetate · CPC title

• C08L1/10

  Esters of organic acids {, i.e. acylates} · CPC title