Derivatives of native lignin

• US 9,708,490 B2
• Filed: 01/05/2016
• Issued: 07/18/2017
• Est. Priority Date: 05/28/2009
• Status: Active Grant

• Current Assignee: Suzano Canada Inc. (Suzano S.A.)
• Original Assignee: Fibria Innovations Inc. (Suzano S.A.)
• Inventors: Pye, Edward Kendall, Balakshin, Mikhail Yurevich, Berlin, Alex, Dellicolli, Humbert Thomas, Grunert, Chadrick Adam Nathaniel Jordan, Gutman, Vera Maximenko, Ortiz, Darwin
• Primary Examiner(s): CHIN, HUI H
• Application Number:
  US14/988,515
• Publication Number:
  US 20160145399A1
• Time in Patent Office: 560 Days
• Field of Search: 524 13
• CPC Class Codes: A23K 10/32 from hydrolysates of wood or straw
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A61K 36/15 Pinaceae (Pine family), e.g. pine or cedar
• CPC Class Codes: A61K 36/48 Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
• CPC Class Codes: A61K 36/54 Lauraceae (Laurel family), e.g. cinnamon or sassafras
• CPC Class Codes: A61K 36/76 Salicaceae (Willow family), e.g. poplar
• CPC Class Codes: B27N 3/002 characterised by the type of binder compositions of macromolecular compounds C08L
• CPC Class Codes: C07G 1/00 Lignin; Lignin derivatives
• CPC Class Codes: C08H 6/00 Macromolecular compounds derived from lignin, e.g. tannins, humic acids
• CPC Class Codes: C08J 2397/00 Characterised by the use of lignin-containing materials of polysaccharides C08J2301/00 - C08J2305/00
• CPC Class Codes: C08J 3/00 Processes of treating or compounding macromolecular substances
• CPC Class Codes: C08K 5/13 Phenols; Phenolates
• CPC Class Codes: C08L 2201/52 Aqueous emulsion or latex, e.g. containing polymers of a glass transition temperature (Tg) below 20°C
• CPC Class Codes: C08L 2207/04 Thermoplastic elastomer
• CPC Class Codes: C08L 23/02 not modified by chemical after-treatment
• CPC Class Codes: C08L 57/00 Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08L 91/06 Waxes
• CPC Class Codes: C08L 97/005 Lignin
• CPC Class Codes: C08L 97/02 Lignocellulosic material, e.g. wood, straw or bagasse manufacture of articles made from lignocellulosic material by dry processes B27N
• CPC Class Codes: C09K 15/06 containing oxygen
• CPC Class Codes: D21C 11/0007 : Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for volatile compounds obtained by decomposition of spent liquors in order to regenerate them D21C11/125; compounds obtained by fractionating the liquors in order to regenerate them D21C11/0042
• CPC Class Codes: D21H 11/00 : Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
• CPC Class Codes: Y02P 20/582 : Recycling of unreacted starting or intermediate materials
• CPC Class Codes: Y02P 60/87 : Re-use of by-products of food processing for fodder production

Abstract

The present invention provides derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.

Claims

1. A lignin derivative recovered from a pulping process of a lignocellulosic biomass, wherein said lignin derivative has an aliphatic hydroxyl content of from 0.001 mmol/g to 2.35 mmol/g, and an ethoxyl content of from 0.001 mmol/g to 2 mmol/g.

2. The lignin derivative according to claim 1, wherein the derivative has an aliphatic hydroxyl content of about 2.25 mmol/g or less.

3. The lignin derivative according to claim 1, wherein the derivative has an aliphatic hydroxyl content of about 1.75 mmol/g or less.

4. The lignin derivative according to claim 1, wherein the derivative has an aliphatic hydroxyl content of about 0.1 mmol/g or greater.

5. The lignin derivative according to claim 1, wherein the derivative has a normalized RSI of 15 or greater.

6. The lignin derivative according to claim 1, wherein the lignin is derived from softwood biomass.

7. The lignin derivative according to claim 1, wherein the lignin is derived from annual fibre biomass.

8. The lignin derivative according to claim 1, wherein the lignin is derived from hardwood biomass.

9. The lignin derivative according to claim 1, wherein the pulping process is selected from the group consisting of steam explosion, dilute acid hydrolysis, ammonia fiber expansion, autohydrolysis, kraft and modifications thereof, soda pulping and modifications thereof, sulphite pulping, and organosolv processes.

10. The lignin derivative according to claim 1, wherein the pulping process is a kraft process or a modification thereof.

11. The lignin derivative according to claim 1, wherein the pulping process is an organosolv process.

12. A composition comprising the lignin derivative according to claim 1 and a polymer-forming component.

13. The lignin derivative according to claim 1, wherein the ethoxyl content is from 0.05 mmol/g to 2 mmol/g.

14. The lignin derivative according to claim 1, wherein the ethoxyl content is from 0.1 mmol/g to 2 mmol/g.

15. The lignin derivative according to claim 1, wherein the ethoxyl content is from 0.001 mmol/g to 1.4 mmol/g.

16. The lignin derivative according to claim 1, wherein said lignin derivative further has a phenolic hydroxyl content from 2 mmol/g to 8 mmol/g.