Lignin-derived thermoplastic co-polymers and methods of preparation

Inactive Publication Date: 2013-05-09
UT BATTELLE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention relates to lignin-based thermoplastics that have significant strength and durability, while being easy to mold and have elasticity. The methods described in the patent allow for the production of different thermoplastics with various mechanical properties. The crosslinked lignin used in the thermoplastics has a mild crosslinking process, making it easy to melt-process. The resulting thermoplastics are melt-processible and have a glass transition temperature of at least 100°C, as well as being soluble in polar organic solvents or aqueous alkaline solutions. The crosslinked lignin component used in the thermoplastics contributes to enhanced melt-processibility of the final product.

Problems solved by technology

Significant commercial potential exists in the conversion of lignin to high-value end products (i.e., functional materials), but lignin remains a highly difficult and challenging material to convert into such useful products.
Although functional plastic materials have been produced from lignin, these materials are generally highly-crosslinked thermosets, which are not melt-processible (and hence, not recyclable).
Furthermore, due to their rigid and brittle character, the known lignin-containing plastics generally lack the rubber elasticity, strength, and toughness required for use in many industrial and commercial applications (e.g., automobile interior or exterior materials).
Moreover, the known lignin-containing plastics are generally not amenable for being adjusted or fine-tuned in such characteristics as glass transition temperature (Tg), degree of stiffness (i.e., rigidity), ductility, tensile failure strength, and toughness, thereby significantly limiting their range of applications.

Method used

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  • Lignin-derived thermoplastic co-polymers and methods of preparation
  • Lignin-derived thermoplastic co-polymers and methods of preparation
  • Lignin-derived thermoplastic co-polymers and methods of preparation

Examples

Experimental program
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Effect test

example 1

Controlled Crosslinking of Lignin

[0059]The process for crosslinking lignin described in this example can be generally summarized by the following reaction scheme:

[0060]A 1-L round-bottomed flask was equipped with a large magnetic stir bar and placed in a heating mantle. 100 g of organosolv lignin (as received, not dried, having a MW of 1840 g / mol, polydispersity index (ratio of weight average to number average molecular weights) of 122, and Tg of 108° C.) were added to the flask. Lignin was dissolved using 200 mL NaOH solution (pH>14) and 300 mL of millipure water, for a final concentration of 16 wt % solids. Once the lignin appeared fully dissolved, the flask was fitted with an addition funnel. 120 mL of formalin solution (10 wt % in buffered solution) were added dropwise to the lignin solution with stirring, at 80° C. After two hours, an additional 120 mL of formalin (10 wt % in buffer solution) were added to the reaction. Reaction continued for four additional hours (six hours to...

example 2

Copolymerization Reactions of Crosslinked Lignin

[0063]I. Copolymerization Reaction of Crosslinked Lignin with Carboxy-Functionalized Polybutadiene

[0064]The process for copolymerizing crosslinked lignin with carboxy-functionalized polybutadiene described in this example can be generally summarized by the following reaction scheme. The long curved lines shown in the final product represent carboxy-functionalized polybutadiene that has been attached to the crosslinked lignin.

[0065]As-received lignin was reacted with dicarboxy-terminated polybutadiene soft segment (Mn 4,200 g / mol) in the presence of formalin at 1:1 F / L ratio with KOH in 1,4-dioxane solvent (with KOH concentration of 2.4 mmol / 40 mL solvent) for 24 hours at 100° C. Different amounts of lignin were loaded to obtain 9, 13, 17, and 22 wt % lignin, respectively, in the feed compositions. All the resulting lignin-polybutadiene copolymers were isolated via precipitation into methanol and dried under reduced pressure at 50° C. f...

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Abstract

The present invention relates to a crosslinked lignin comprising a lignin structure having methylene or ethylene linking groups therein crosslinking between phenyl ring carbon atoms, wherein said crosslinked lignin is crosslinked to an extent that it has a number-average molecular weight of at least 10,000 g / mol, is melt-processible, and has either a glass transition temperature of at least 100° C., or is substantially soluble in a polar organic solvent or aqueous alkaline solution. Thermoplastic copolymers containing the crosslinked lignin are also described. Methods for producing the crosslinked lignin and thermoplastic copolymers are also described.

Description

[0001]This invention was made with government support under Prime Contract No. DE-AC05-00OR22725 awarded by the U.S. Department of Energy. The government has certain rights in the invention.FIELD OF THE INVENTION[0002]The present invention relates generally to thermoplastic biopolymers, and more particularly, to such polymers in which lignin is incorporated.BACKGROUND OF THE INVENTION[0003]Lignin, a complex O-methyl-substituted polyphenol found in lignocellulosic biomass, is the third most abundant natural polymer (after cellulose and chitin, respectively) that accounts for up to 30% by weight of wood. Lignin is a valuable by-product of the pulp and paper industry produced in quantities exceeding 200 million metric tons annually, but the vast majority of this by-product (>99%) is not isolated but combusted in the form of “black liquor” to meet the energy needs of the mill. Future and upcoming biorefineries that process lignocellulosic materials for the production of fuel and comm...

Claims

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Application Information

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IPC IPC(8): C08H7/00C08F8/00C08F289/00C08G63/91C08F36/06C08G65/331
CPCC08J3/243C08J3/246C08J2309/00C08J2367/04C08J2397/00C08G65/2612C08F8/00C08G63/91C08G65/40C08H6/00C08F36/06C08L71/02C08L2205/05C08L97/00
Inventor NASKAR, AMIT K.SAITO, TOMONORIPICKEL, JOSEPH M.BAKER, FREDERICK S.EBERLE, CLIFFNORRIS, JR., ROBERT E.MIELENZ, JONATHAN RICHARD
Owner UT BATTELLE LLC
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