# US 8,541,556 B1 · Lignin derivatives and uses thereof

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- Number: US 8,541,556 B1
- Document ID: US8541556B1
- Status: Granted
- Kind: B1
- Application number: 13/738,424
- Filed: 2013-01-10
- Published: 2013-09-05
- Granted: 2013-09-24
- Earliest claimed: 2013-01-10
- Assignees: Empire Technology Development LLC
- Applicants: Empire Technology Development LLC
- Inventors: Yansong Gu
- Web page: https://patentgrep.com/patent/US8541556B1

## CPC

- C07G 1/00: Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00})
- C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids}
- C08L 97/005: {Lignin}
- C07G: COMPOUNDS OF UNKNOWN CONSTITUTION (sulfonated fats, oils or waxes of undetermined constitution C07C309/62)
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

An article including a lignin derivative, where the lignin derivative includes a moiety derived from an antimicrobial compound. Also provided are methods of inhibiting microbial growth with an article including a lignin derivative.

## Claims

### Claim 1

An article comprising a lignin derivative, wherein the lignin derivative comprises a moiety derived from an antimicrobial compound, and the article is a moldable thermoplastic material, and the lignin derivative is represented by Formula IV:
wherein:
R1, R2, R4, and R5 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
R3 is OH or SH; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.

### Claim 2 (depends on 1)

The article of claim 1, wherein R1, R2, R4, and R5 are each H and R3 is OH.

### Claim 3

An article comprising a lignin derivative, wherein the lignin derivative comprises a moiety derived from an antimicrobial compound, and the article is a moldable thermoplastic material, and the lignin derivative is represented by Formula IIA:
wherein:
R6, R7, R8, R9, R10, R11, R12, R13, and R14 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
L is an alkylene moiety or polyalkyleneoxy moiety; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.

### Claim 4 (depends on 3)

The article of claim 3, wherein L is —CH2CH(OH)CH2—.

### Claim 5 (depends on 3)

The article of claim 3, wherein L is —CH2CH(OH)CH2OCH2CH(OH)CH2—.

### Claim 6 (depends on 3)

The article of claim 3, wherein R6, R7, R8, R9, R10, R11, R12, R13, and R14 are each independently H or chloro.

### Claim 7 (depends on 3)

The article of claim 3, wherein the moiety derived from the antimicrobial compound comprises:

### Claim 8 (depends on 3)

The article of claim 3, wherein the moiety derived from the antimicrobial compound comprises:

### Claim 9 (depends on 1)

A method of inhibiting microbial growth, the method comprising: contacting one or more microbes with an article according to claim 1.

### Claim 10 (depends on 9)

The method of claim 9, wherein the one or more microbes comprise bacteria.

### Claim 11 (depends on 9)

The method of claim 9, wherein the one or more microbes comprise fungi.

### Claim 12 (depends on 3)

A method of inhibiting microbial growth, the method comprising: contacting one or more microbes with an article according to claim 3.

### Claim 13

A method of forming a lignin derivative, the method comprising:
contacting a lignin-containing material with a compound of Formula VI to form the lignin derivative, wherein the lignin derivative comprises a moiety of Formula IIA:
R6, R7, R8, R9, R10, R11, R12, R13, and R14 are each independently H, halo, alkyl, alkenyl, aryl or heteroaryl;
L is an alkylene moiety or polyalkyleneoxy moiety; and
O-Lignin is a lignin residue derived from a hydroxyl group of lignin.

### Claim 14 (depends on 13)

The method of claim 13, further comprising at least partially depolymerizing the lignin.

### Claim 15 (depends on 14)

The method of claim 14, wherein the depolymerizing comprises a hydrogenolysis reaction.

### Claim 16 (depends on 15)

The method of claim 15, wherein the hydrogenolysis reaction is conducted in the presence of a transition metal catalyst.

### Claim 17 (depends on 16)

The method of claim 16, wherein the transition metal catalyst comprises nickel.

### Claim 18 (depends on 16)

The method of claim 16, wherein the transition metal catalyst further comprises a carbene ligand.

### Claim 19 (depends on 13)

The method of claim 13, wherein the contacting is conducted in the presence of a base.

### Claim 20 (depends on 19)

The method of claim 19, wherein the base comprises an alkali metal hydroxide, a carbonate, a secondary amine, an aromatic amine, or a tertiary amine.

### Claim 21 (depends on 13)

The method of claim 13, wherein contacting is conducted in the presence of an acid.

### Claim 22 (depends on 21)

The method of claim 21, wherein the acid comprises hydrochloric acid, sulfuric acid, acetic acid, trifluoroacetic acid, or phosphoric acid.