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Functionalized cellulose nanocrystal materials and methods of preparation

Jeffrey Paul Youngblood

Patent #
US-2019092926-A1
interested LPs
Identification Number
- -
Issue Date
2020-06-02
Organization
Purdue Office of Technology Commercialization
Date Added
2023-01-01
Tech Transfer Org
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CHatgpt summary & Analysis

The patent is about a green process to modify cellulose nanocrystals (CNCs) by making them hydrophobic, which can be used in various food and agriculture applications. The process involves using an aqueous lactic acid syrup as a solvent to produce a stable water suspension of CNCs, which are then esterified with carboxylic acids, biodiesel or plant oils with long hydrocarbon chains such as fatty acids to create a polylactic acid (PLA) grafted CNCs. This process is environmentally friendly as it does not require toxic reagents or organic solvents, and it is cost-effective as it enables the reuse of reagents in subsequent reactions.

Potential food and agricultural uses for this technology include:
- Packaging materials that increase shelf life and reduce food waste: CNCs can be used to create films and coatings that prevent moisture and oxygen from reaching food, keeping it fresh for longer periods.
- Edible films: CNCs can be used to create edible films that serve as carriers for nutrients and flavors, providing a healthier and more convenient way to consume food supplements or functional ingredients.
- Texturizers: CNCs can be used as a fat replacer or texture modifier in processed foods, providing a healthier and more sustainable alternative to traditional thickeners and stabilizers.
- Pesticide delivery systems: CNCs can be used to encapsulate and deliver pesticides to crops, reducing the amount of chemicals needed and minimizing their impact on the environment.

The market sizes or values for each use case are not provided in the patent, but further research can be conducted to estimate their potential.

This patent warrants further due diligence to explore the commercial potential based on GFRP mission because:
- It aligns with GFRP's mission to revolutionize the food, protein, and agriculture industries by developing nascent technologies into new products and services that meet the current and future needs of industrial partners, farmers, and consumers.
- It has the potential to catalyze economic and job growth in rural communities by providing new opportunities for farmers and suppliers to participate in value-added activities.
- It drives applied innovation and technology commercialization in university ecosystems across the United States by leveraging academic research and expertise to create practical solutions for the food and agriculture sectors.

Citations:
- Big Idea Ventures (n.d.). Generation Food Rural Partners. https://bigideaventures.com/generation-food-rural-partners/
- Google Patents. Functionalized cellulose nanocrystal materials and methods of preparation. https://patents.google.com/patent/US20190092926A1/en?oq=US-2019092926-A1

Abstract

The surface hydrophobization of cellulose nanocrystals (CNCs) by carboxylic acids, biodiesel, or plant oils was conducted via there herein disclosed green process using an one-pot synthetic method. In the process, an aqueous lactic acid syrup served as a solvent to provide a stable and well-dispersed water suspension of CNCs and participated in esterification reactions to produce an intermediate product of polylactic acid (PLA) oligomer grafted CNCs (CNC-g-PLA). This solvent and intermediate product system allows for an in situ solvent exchange from water to lactic acid without prior drying of the CNCs and a subsequent efficient esterification reaction of CNCs with carboxylic acids or esters having a long hydrocarbon chain (FAs). Another advantage of the disclosed process is the ability to reuse the reagents in the subsequent reaction in order to reduce the production cost. Grafting of renewable materials on the surface of CNCs was developed by polyesterification that is capable of being environmentally friendly and mass-produced without any organic solvents or toxic reagents.

Claims

  1. A composition of cellulose nanoparticles, wherein the chemical structure of the cellulose nanoparticles comprising a glucose unit of formula I: Figure US20190092926A1-20190328-C00007

Wherein R1 is H or
Figure US20190092926A1-20190328-C00008

wherein each R1 in formula I may be the same or different, and at least one R1 is not H;
X is C1-C8 straight or branched carbon linker, wherein X is optionally substituted with C1-C4 alkyl, F, Cl, —OMe, or OEt;
R2 is a C5-C10 hetero or carbon aryl wherein the hetero aryl comprising N, O or S; a C1-C24 straight or branched alkyl or alkenyl, wherein the C1-C24 straight or branched alkyl or alkenyl is optionally substituted with a C5-C10 hetero or carbon aryl wherein the hetero aryl comprising N, O or S, a C1-C4 alkyl, F, Cl, —OMe, or OEt; and
n is 10-20,000, p is 1-12.
2. The composition of claim 1, wherein X is —CH(CH3)—.
3. The composition of claim 1, wherein R2 is C4-C20 straight or branched alkyl or alkenyl.
4. The composition of claim 3, wherein the R2 is selected from the group consisting of:
Figure US20190092926A1-20190328-C00009

  1. The composition of claim 1 comprising cellulose nanoparticle with a length dimension of about 50 nm to about 2000 nm; a lateral dimension of about 2 nm to about 20 nm; and an aspect ratio of about 2.5 to about 1000.
  2. The composition of claim 1, wherein the cellulose nanoparticle is cellulose nanocrystal or cellulose nanofibril.
  3. The composition of claim 1, wherein n is between 100-5000, p is 2-6.
  4. A method of making the composition of claim 1, comprising: a) contacting cellulose nanoparticles with water, a catalyst suitable for esterification, and a carboxylic acid with the formula of HOOC—X—OH, wherein X is defined in claim 1, and heating the formed mixture; b) removing water to facilitate the esterification reaction; and c) adding a carboxylic acid with the formula of HOOCR2, wherein R2 is defined in claim 1.
  5. The method of claim 8, wherein the step c) of adding a carboxylic acid with the formula of HOOCR2 is carried out in step a) prior to the heating.
  6. The method of claim 8, wherein X is —CH(CH3)—, and wherein R2 is C4-C20 straight or branched alkyl or alkenyl.
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Market Category & Size
Nanocellulose
$1.26B by 2028
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