WO1993025622A1 - Method of increasing lignin solubility - Google Patents
Method of increasing lignin solubility Download PDFInfo
- 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
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- surfactant
- lignin
- alkyl
- alkyl glycoside
- binder
- Prior art date
Links
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.
Landscapes
- 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)
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 |
---|---|---|---|
DK77492A DK77492D0 (sk) | 1992-06-12 | 1992-06-12 | |
DK0774/92 | 1992-06-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993025622A1 true WO1993025622A1 (en) | 1993-12-23 |
Family
ID=8097400
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 (sk) |
DK (1) | DK77492D0 (sk) |
WO (1) | WO1993025622A1 (sk) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO1998031761A1 (en) * | 1997-01-14 | 1998-07-23 | Neste Chemicals Oy | Adhesives for fiber boards and a process for the preparation thereof |
US6245269B1 (en) | 1997-01-14 | 2001-06-12 | Neste Chemicals Oy | Process for preparing fiber boards |
Citations (3)
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 |
-
1992
- 1992-06-12 DK DK77492A patent/DK77492D0/da not_active Application Discontinuation
-
1993
- 1993-06-10 WO PCT/DK1993/000199 patent/WO1993025622A1/en active Application Filing
- 1993-06-10 AU AU43114/93A patent/AU4311493A/en not_active Abandoned
Patent Citations (3)
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO1998031761A1 (en) * | 1997-01-14 | 1998-07-23 | Neste Chemicals Oy | Adhesives for fiber boards and a process for the preparation thereof |
US6245269B1 (en) | 1997-01-14 | 2001-06-12 | Neste Chemicals Oy | Process for preparing fiber boards |
Also Published As
Publication number | Publication date |
---|---|
DK77492D0 (sk) | 1992-06-12 |
AU4311493A (en) | 1994-01-04 |
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