WO1993025622A1 - Method of increasing lignin solubility - Google Patents

Method of increasing lignin solubility Download PDF

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Publication number
WO1993025622A1
WO1993025622A1 PCT/DK1993/000199 DK9300199W WO9325622A1 WO 1993025622 A1 WO1993025622 A1 WO 1993025622A1 DK 9300199 W DK9300199 W DK 9300199W WO 9325622 A1 WO9325622 A1 WO 9325622A1
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WO
WIPO (PCT)
Prior art keywords
surfactant
lignin
alkyl
alkyl glycoside
binder
Prior art date
Application number
PCT/DK1993/000199
Other languages
English (en)
French (fr)
Inventor
Birgitte Yde
Original Assignee
Novo Nordisk A/S
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novo Nordisk A/S filed Critical Novo Nordisk A/S
Priority to AU43114/93A priority Critical patent/AU4311493A/en
Publication of WO1993025622A1 publication Critical patent/WO1993025622A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J197/00—Adhesives based on lignin-containing materials
    • C09J197/005—Lignin

Definitions

  • This invention relates to a method of preparing a solution of lignin at high concentration, to a method of preparing a binder using said solution, and to a method of producing a wood composite using said binder.
  • lignin is only sparingly soluble in water at weakly acidic to neutral pH.
  • solubility of lignin can be increased by incorporating a surfactant.
  • the invention provides a method of increasing the solubility of lignin, characterized by incorporating a surfactant and a lignin solution, characterized by comprising a surfactant. Further, the invention also provides a method for producing a binder for wood products from lignin, characterized by comprising treatment of such a lignin solution with a phenol oxidizing enzyme system. Finally, the invention provides a method of producing a wood composite from wood fibre material, characterized by comprising production of a binder in this way, coating the wood fibre material with said binder, followed by pressing and heating.
  • the invention is applicable to any quality of lignin, particularly non- sulfonated lignin such as indulin which results in a strong binder when treated with a phenol-oxidizing system, but has a low solubility in water at weakly acidic to neutral pH where these enzymes are mostly active.
  • Lignin can be used in an amount of 25-250 g/1, and solutions containing above 100 g/l of lignin can be obtained.
  • the surfactant used in the invention may be nonionic, anionic, cationic or zwitterionic (amphoteric).
  • suitable nonionics are alkyl glycosides, alkyl glycoside esters and ethoxylated alcohols and phenols.
  • the alkyl glycoside (ester) used in the invention consists of an alkyl group linked to a saccharide moiety through a glycosidic bond.
  • the saccharide moiety may optionally be esterified.
  • the saccharide moiety is a mono- or oligosaccharide, preferably a mono-, di- or trisaccharide, preferably consisting of hexose units, particularly of aldose units.
  • Some preferred saccharide moieties are of the type G n where G is a glucose group, n is 1 , 2 or 3, and the glucose units are linked through ⁇ - 1 ,4 bonds, i.e. glucose, maltose or maltotriose.
  • the alkyl glycoside preferably contains a straight-chain saturated unsubstituted C 6 -C 18 alkyl, particularly C ⁇ -C 12 .
  • the alkyl glycoside ester is preferably a monoester and preferably contains a C.-C 4 alkyl group and a straight-chain saturated unsubstituted C 6 -C 1 ⁇ acyl group, particularly C ⁇ -C 12 .
  • the ester group is preferably attached to the C atom in the 6- position of a glucose moiety.
  • the glycoside bond may be in the a- or ⁇ - conformation, or a mixture of the two may be used.
  • Suitable anionic surfactants are linear alkylbenzene sulfonate (LAS), alcohol ether sulfate (AES) and alkyl ether phosphate.
  • suitable cationic surfactants are quaternary ammonium salts:
  • suitable zwitterionic (amphoteric) surfactants are substituted betaines, e.g. alkylamide propyl betaine.
  • the surfactant is generally added in an amount of 5-100 g/l.
  • Phenol oxidizing enzyme system The enzyme system used in the invention consists of a suitable oxidase together with 0 2 or a suitable peroxidase together with H 2 0 2 .
  • Suitable enzymes are those which oxidize and polymerize aromatic compounds such as phenols and lignin.
  • Suitable enzymes are catechol oxidase (EC 1.10.3.1), laccase (EC 1.10.3.2) and peroxidase (EC 1.11.1.7).
  • Some preferred enzymes are peroxidase derived from a strain of Coprinus, e.g. C. cinereus or C. macrorhizus, peroxidase from Bacillus, e.g. ⁇ . pumilus and laccase from Trametes, e.g. T. versicolor (previously called Polyporus). It may be preferable to use two different phenol oxidizing enzymes together.
  • the amount of enzyme should generally be in the range 10-10,000
  • H 2 0 2 Molecular oxygen from the atmosphere will usually be present in sufficient quantity.
  • a suitable amount of H 2 0 2 will usually be in the range 0.01 -10 mM, particularly 1-10 mM.
  • Suitable conditions for the enzymatic treatment of lignin to produce binder are known in the art. Typical conditions are 20-60°C and pH 5-6 for laccase, and 20-60°C and pH 7-8 for peroxidase.
  • the binder to wood fibre material and pressing under heat to produce a wood composite can be done by methods known in the art.
  • a typical example is production of particle board from wood particles.
  • the binder is applied by spraying in an amount of 40-100 g/kg of wood fibre material, and pressing is typically done by compressing for 2-4 minutes at a pressure of 20-40 kg/cm 2 (2-4 Pa) with temperature rising form 35 to 190°C in 20 seconds.
  • APG increases the lignin solubility 5 particularly at acid pH, and glucose-C 10 particularly at alkaline pH.
  • Fig. 1 shows the solibility of indulin in the 20 presence of surfactants as a function of pH. It appears that at pH 7, the solubility of indulin is 12.7 mg/ml in the absence of surfactant, and 39, 45 and 29 mg/ml in the presence of 5% Empigen, 5% Nansa 1169/P and 5% APG, respectively.
  • EXAMPLE 3 shows the solibility of indulin in the 20 presence of surfactants as a function of pH. It appears that at pH 7, the solubility of indulin is 12.7 mg/ml in the absence of surfactant, and 39, 45 and 29 mg/ml in the presence of 5% Empigen, 5% Nansa 1169/P and 5% APG, respectively.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
PCT/DK1993/000199 1992-06-12 1993-06-10 Method of increasing lignin solubility WO1993025622A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU43114/93A AU4311493A (en) 1992-06-12 1993-06-10 Method of increasing lignin solubility

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK0774/92 1992-06-12
DK77492A DK77492D0 (enrdf_load_stackoverflow) 1992-06-12 1992-06-12

Publications (1)

Publication Number Publication Date
WO1993025622A1 true WO1993025622A1 (en) 1993-12-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK1993/000199 WO1993025622A1 (en) 1992-06-12 1993-06-10 Method of increasing lignin solubility

Country Status (3)

Country Link
AU (1) AU4311493A (enrdf_load_stackoverflow)
DK (1) DK77492D0 (enrdf_load_stackoverflow)
WO (1) WO1993025622A1 (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998031761A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Adhesives for fiber boards and a process for the preparation thereof
WO1998031763A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Lignin-based adhesives and a process for the preparation thereof
WO1998031764A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Lignin-based adhesives for particle board manufacture
US6245269B1 (en) 1997-01-14 2001-06-12 Neste Chemicals Oy Process for preparing fiber boards

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3037992A1 (de) * 1980-10-08 1982-08-19 Gesellschaft für Biotechnologische Forschung mbH (GBF), 3300 Braunschweig Verfahren zur herstellung eines bindemittels fuer holzwerkstoffe
US4357454A (en) * 1980-09-02 1982-11-02 Eka Ab Binder
EP0275544A2 (de) * 1986-12-24 1988-07-27 PFLEIDERER UNTERNEHMENSVERWALTUNG GmbH & Co KG Emissionsarmes Bindemittel für holz- und cellulosehaltige Werkstoffe

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357454A (en) * 1980-09-02 1982-11-02 Eka Ab Binder
DE3037992A1 (de) * 1980-10-08 1982-08-19 Gesellschaft für Biotechnologische Forschung mbH (GBF), 3300 Braunschweig Verfahren zur herstellung eines bindemittels fuer holzwerkstoffe
EP0275544A2 (de) * 1986-12-24 1988-07-27 PFLEIDERER UNTERNEHMENSVERWALTUNG GmbH & Co KG Emissionsarmes Bindemittel für holz- und cellulosehaltige Werkstoffe

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 71, No. 16, 20 October 1969, (Columbus, Ohio, USA), SHPENZER N.P. et al., "Solubility of Natural Resins", the abstract No. 72139r; & TR. LENINGRAD. TEKHNOL. INST. TSELLYUL.-BUM. PROM., 1968, 21, 265-74. *
CHEMICAL ABSTRACTS, Volume 97, No. 24, 13 December 1982, (Columbus, Ohio, USA), HEIKKI PALONEN et al., "Surfactant Behavior of Wood Resin Components. The Solubility of Rosin and Fatty Acid Soaps in Water and in Salt Solutions", page 93, the Abstract No. 199768n; & SVEN. PAPPERSTIDN., 1982, 85 (12), 93-99. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998031761A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Adhesives for fiber boards and a process for the preparation thereof
WO1998031763A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Lignin-based adhesives and a process for the preparation thereof
WO1998031764A1 (en) * 1997-01-14 1998-07-23 Neste Chemicals Oy Lignin-based adhesives for particle board manufacture
US6245269B1 (en) 1997-01-14 2001-06-12 Neste Chemicals Oy Process for preparing fiber boards

Also Published As

Publication number Publication date
AU4311493A (en) 1994-01-04
DK77492D0 (enrdf_load_stackoverflow) 1992-06-12

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