AU1680792A - Improved lignin-based wood adhesives - Google Patents

Improved lignin-based wood adhesives

Info

Publication number: AU1680792A
Authority: AU; Australia
Prior art keywords: adhesive; phenol; lignin; organosolv lignin; formaldehyde
Prior art date: 1991-04-09
Legal status (The legal status 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 status listed.): Abandoned

Application number

AU16807/92A

Other languages

English (en)

Inventor

Jacob Ash

Albert W. Creamer

Jairo H. Lora

Chih Fae Wu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Alcell Technologies Inc

Original Assignee

Alcell Technologies Inc

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.)

1991-04-09

Filing date

1992-04-09

Publication date

1992-11-17

1992-04-09 Application filed by Alcell Technologies Inc filed Critical Alcell Technologies Inc

1992-11-17 Publication of AU1680792A publication Critical patent/AU1680792A/en

Status Abandoned legal-status Critical Current

Links

229920005610 lignin Polymers 0.000 title claims description 371
239000000853 adhesive Substances 0.000 title claims description 309
230000001070 adhesive effect Effects 0.000 title claims description 308
239000002023 wood Substances 0.000 title claims description 42
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 258
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 205
229920001568 phenolic resin Polymers 0.000 claims description 162
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 148
229920005989 resin Polymers 0.000 claims description 90
239000011347 resin Substances 0.000 claims description 90
239000000203 mixture Substances 0.000 claims description 80
239000007787 solid Substances 0.000 claims description 78
239000003513 alkali Substances 0.000 claims description 63
238000006243 chemical reaction Methods 0.000 claims description 37
239000007788 liquid Substances 0.000 claims description 32
239000003607 modifier Substances 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 28
239000000843 powder Substances 0.000 claims description 23
239000006185 dispersion Substances 0.000 claims description 19
239000012670 alkaline solution Substances 0.000 claims description 12
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 11
230000005494 condensation Effects 0.000 claims description 11
239000002270 dispersing agent Substances 0.000 claims description 10
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 8
239000002131 composite material Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims description 4
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims description 4
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 claims description 4
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
239000000908 ammonium hydroxide Substances 0.000 claims description 4
230000009477 glass transition Effects 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 claims description 2
KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 claims description 2
ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 claims description 2
ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-UHFFFAOYSA-N 0.000 claims description 2
244000073231 Larrea tridentata Species 0.000 claims description 2
235000006173 Larrea tridentata Nutrition 0.000 claims description 2
229940106691 bisphenol a Drugs 0.000 claims description 2
229960002126 creosote Drugs 0.000 claims description 2
KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 claims description 2
COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims description 2
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 2
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 2
235000012141 vanillin Nutrition 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 136
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
238000004519 manufacturing process Methods 0.000 description 45
238000000034 method Methods 0.000 description 32
239000011120 plywood Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
235000012431 wafers Nutrition 0.000 description 29
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
238000006116 polymerization reaction Methods 0.000 description 28
238000007792 addition Methods 0.000 description 27
239000003292 glue Substances 0.000 description 26
230000002860 competitive effect Effects 0.000 description 24
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
239000004202 carbamide Substances 0.000 description 22
238000009472 formulation Methods 0.000 description 18
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 17
238000012360 testing method Methods 0.000 description 17
239000005011 phenolic resin Substances 0.000 description 16
229910021529 ammonia Inorganic materials 0.000 description 14
150000001875 compounds Chemical class 0.000 description 14
239000000243 solution Substances 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000000654 additive Substances 0.000 description 12
229920000642 polymer Polymers 0.000 description 12
239000010410 layer Substances 0.000 description 11
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 9
230000008569 process Effects 0.000 description 9
239000012792 core layer Substances 0.000 description 8
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 8
-1 accelerators Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000000945 filler Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000006467 substitution reaction Methods 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
229920001732 Lignosulfonate Polymers 0.000 description 6
241000183024 Populus tremula Species 0.000 description 6
238000001035 drying Methods 0.000 description 6
238000011068 loading method Methods 0.000 description 6
238000003825 pressing Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011342 resin composition Substances 0.000 description 6
239000004034 viscosity adjusting agent Substances 0.000 description 6
229920005611 kraft lignin Polymers 0.000 description 5
239000011230 binding agent Substances 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
239000000470 constituent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000446 fuel Substances 0.000 description 4
238000013019 agitation Methods 0.000 description 3
238000012093 association test Methods 0.000 description 3
238000005452 bending Methods 0.000 description 3
239000011094 fiberboard Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000004537 pulping Methods 0.000 description 3
BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 2
229920001342 Bakelite® Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000004637 bakelite Substances 0.000 description 2
239000011121 hardwood Substances 0.000 description 2
230000006872 improvement Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000002699 waste material Substances 0.000 description 2
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
ZMWAXVAETNTVAT-UHFFFAOYSA-N 7-n,8-n,5-triphenylphenazin-5-ium-2,3,7,8-tetramine;chloride Chemical compound [Cl-].C=1C=CC=CC=1NC=1C=C2[N+](C=3C=CC=CC=3)=C3C=C(N)C(N)=CC3=NC2=CC=1NC1=CC=CC=C1 ZMWAXVAETNTVAT-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000002028 Biomass Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
102000051325 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
235000005018 Pinus echinata Nutrition 0.000 description 1
241001236219 Pinus echinata Species 0.000 description 1
235000017339 Pinus palustris Nutrition 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229920005550 ammonium lignosulfonate Polymers 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
238000003475 lamination Methods 0.000 description 1
239000012705 liquid precursor Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000000123 paper Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003265 pulping liquor Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011122 softwood Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1

Classifications

- 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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- 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
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Adhesives Or Adhesive Processes (AREA)
Phenolic Resins Or Amino Resins (AREA)

AU16807/92A 1991-04-09 1992-04-09 Improved lignin-based wood adhesives Abandoned AU1680792A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68256591A	1991-04-09	1991-04-09
US682565		1991-04-09

Publications (1)

Publication Number	Publication Date
AU1680792A true AU1680792A (en)	1992-11-17

Family

ID=24740239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU16807/92A Abandoned AU1680792A (en)	1991-04-09	1992-04-09	Improved lignin-based wood adhesives

Country Status (7)

Country	Link
EP (1)	EP0646148A1 (no)
JP (1)	JPH06506967A (no)
AU (1)	AU1680792A (no)
CA (1)	CA2108176A1 (no)
FI (1)	FI934392A7 (no)
NO (1)	NO933601L (no)
WO (1)	WO1992018557A1 (no)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU4596193A (en) *	1992-04-09	1993-11-18	Alcell Technologies Inc.	Lignin in wood composites
DE4331656C2 (de) *	1993-03-12	1999-01-14	Bakelite Ag	Bindemittelgemisch
WO1994024192A1 (en) *	1993-04-09	1994-10-27	Alcell Technologies Inc.	Lignin-based formulations for wood composites
AU725051B2 (en) *	1997-02-27	2000-10-05	Borden Chemical, Inc.	Wood-product laminated composites
JP2005060590A (ja) *	2003-08-18	2005-03-10	Sekisui Chem Co Ltd	接着剤、木質系複合材料、木質系複合材料の製造方法及び接着体の剥離方法
CN101857787B (zh) *	2010-06-13	2011-07-27	北京林业大学	一种生物油酚醛树脂改性淀粉胶粘剂的制备方法
EP3859017A1 (en)	2010-06-26	2021-08-04	Virdia, Inc.	Methods for production of sugar mixtures
IL206678A0 (en)	2010-06-28	2010-12-30	Hcl Cleantech Ltd	A method for the production of fermentable sugars
CN102134305B (zh) *	2011-02-16	2012-07-25	福州大学	一种溶剂型木质素改性环氧树脂固化剂及其制备方法
WO2012137201A1 (en)	2011-04-07	2012-10-11	Hcl Cleantech Ltd.	Lignocellulose conversion processes and products
FI124944B (fi) *	2011-04-08	2015-03-31	Upm Kymmene Corp	Menetelmä sideainekoostumuksen valmistamiseksi, sideainekoostumus, liima-ainekoostumus, kerrostettu komposiittirakenne, ja sideainekoostumuksen ja liimakoostumuksen käyttöjä
US9163169B2 (en)	2012-03-13	2015-10-20	Georgia-Pacific Chemicals Llc	Adhesive compositions having a reduced cure time and methods for making and using same
FI123934B (en)	2012-03-29	2013-12-31	Upm Kymmene Corp	Use of low molecular weight lignin for the preparation of a binder composition
FI123936B2 (en)	2012-03-29	2019-03-29	Upm Kymmene Corp	A method for increasing the reactivity of lignin
US9458298B2 (en)	2012-10-01	2016-10-04	Georgia-Pacific Chemicals Llc	Methods for making lignocellulose containing composite products
US9586338B2 (en)	2012-10-01	2017-03-07	Georgia-Pacific Chemicals Llc	Methods for making lignocellulose containing composite products
NZ711575A (en)	2013-03-14	2017-02-24	Georgia Pacific Chemicals Llc	Binder compositions and methods for making and using same
US9587077B2 (en)	2013-03-14	2017-03-07	Georgia-Pacific Chemicals Llc	Methods for making composite products containing lignocellulose substrates
FI126736B (en)	2013-11-26	2017-04-28	Upm Kymmene Corp	Process for treating lignin and preparing a binder composition
WO2015095841A1 (en)	2013-12-20	2015-06-25	Georgia-Pacific Chemicals Llc	Release aids with adjustable cloud points for creping processes
WO2015116612A1 (en) *	2014-01-28	2015-08-06	Georgia-Pacific Chemicals Llc	Lignin adhesive
CA2944619C (en)	2014-04-02	2021-10-12	Georgia-Pacific Chemicals Llc	Methods for making lignocellulose composite products
WO2015153520A1 (en)	2014-04-02	2015-10-08	Georgia-Pacific Chemicals Llc	Methods for making lignocellulose composite products with oxidative binders and encapsulated catalyst
US9587114B2 (en)	2014-04-02	2017-03-07	Georgia-Pacific Chemicals Llc	Methods for making lignocellulose composite products with oxidative binders and complexed metal catalyst
WO2016057390A1 (en) *	2014-10-07	2016-04-14	Georgia-Pacific Chemicals Llc	Adhesives containing a resin, a kraft lignin, and a surfactant and methods for making and using same
PL3028856T3 (pl)	2014-12-04	2019-10-31	Ball Beverage Packaging Europe Ltd	Urządzenie drukujące
LT3283551T (lt)	2015-04-02	2021-01-25	Stora Enso Oyj	Aktyvintas lignino mišinys, jo gamybos ir naudojimo būdas
US10549921B2 (en)	2016-05-19	2020-02-04	Rexam Beverage Can Company	Beverage container body decorator inspection apparatus
WO2018047772A1 (ja) *	2016-09-09	2018-03-15	出光興産株式会社	リグニン含有樹脂組成物の製造方法及びリグニン含有樹脂成形品
SE543465C2 (en) *	2018-04-20	2021-02-23	Stora Enso Oyj	Process for preparing a bonding resin
SE1850470A1 (en)	2018-04-20	2019-10-21	Stora Enso Oyj	Adhesive formulation comprising lignin
US12515989B2 (en)	2019-08-26	2026-01-06	Walker Industries Holdings Limited	Wax dispersion composition containing lignin for imparting water resistance to gypsum
US11752660B2 (en)	2019-08-26	2023-09-12	Walker Industries Holdings Limited	Aqueous wax emulsions and dispersions and uses thereof
CN112778963B (zh) *	2021-02-09	2023-03-17	河南银金达新材料股份有限公司	一种用于petg膜的透明黏合剂及其制备方法
CN114456759B (zh) *	2022-01-26	2023-07-18	山东大唐宅配家居有限公司	一种高强度环保多层复合板及其制备方法
FI20225456A1 (en) *	2022-05-25	2023-11-26	Fortum Oyj	Process for preparing lignin-phenol-formaldehyde resins with controlled viscosity
FR3155235A1 (fr) *	2023-11-09	2025-05-16	Compagnie Generale Des Etablissements Michelin	Composition adhesive aqueuse comportant une resine thermodurcissable a faible taux de phenol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5010156A (en) *	1988-05-23	1991-04-23	Eastman Kodak Company	Organosolv lignin-modified phenolic resins and method for their preparation

1992
- 1992-04-09 JP JP4509104A patent/JPH06506967A/ja active Pending
- 1992-04-09 WO PCT/US1992/002963 patent/WO1992018557A1/en not_active Ceased
- 1992-04-09 CA CA002108176A patent/CA2108176A1/en not_active Abandoned
- 1992-04-09 EP EP92909872A patent/EP0646148A1/en not_active Ceased
- 1992-04-09 AU AU16807/92A patent/AU1680792A/en not_active Abandoned
1993
- 1993-10-06 FI FI934392A patent/FI934392A7/fi not_active Application Discontinuation
- 1993-10-08 NO NO933601A patent/NO933601L/no unknown

Also Published As

Publication number	Publication date
FI934392A7 (fi)	1993-12-01
EP0646148A4 (en)	1994-06-27
CA2108176A1 (en)	1992-10-10
FI934392A0 (fi)	1993-10-06
WO1992018557A1 (en)	1992-10-29
NO933601L (no)	1993-12-09
NO933601D0 (no)	1993-10-08
JPH06506967A (ja)	1994-08-04
EP0646148A1 (en)	1995-04-05

Publication	Publication Date	Title
AU1680792A (en)	1992-11-17	Improved lignin-based wood adhesives
WO1994024192A1 (en)	1994-10-27	Lignin-based formulations for wood composites
US5202403A (en)	1993-04-13	Lignin modified phenol-formaldehyde resins
EP0635037A1 (en)	1995-01-25	Lignin in wood composites
US6747076B2 (en)	2004-06-08	Furfuryl alcohol and lignin adhesive composition
US4303562A (en)	1981-12-01	Lignin-containing resin adhesive
JP2010502773A (ja)	2010-01-28	低放出性製品のための天然化合物を有する新規な複合バインダー
US5021531A (en)	1991-06-04	Method for recovering and using lignin in adhesive resins by extracting demethylated lignin
JP2019534345A (ja)	2019-11-28	グリオキサール化リグニン組成物
IE81045B1 (en)	1999-11-17	Modified phenol-aldehyde resin and binder system
US20050272892A1 (en)	2005-12-08	Hydrolyzates of soybeans or other soy products as components of thermosetting resins
US20220242995A1 (en)	2022-08-04	Amino resin performance with sulfonated lignin
US4201700A (en)	1980-05-06	Phenol-aldehyde resin composition containing peanut hull extract and an aldehyde
CA1068426A (en)	1979-12-18	Adhesive for the manufacture of plywood particle boards, fiber boards and similar products
US3254038A (en)	1966-05-31	Adhesive composition comprising phenolic resin, a tannin and an alkali metal hydroxide
US4201851A (en)	1980-05-06	Organic phenol extract compositions of pecan pith agricultural residues and method
US4200723A (en)	1980-04-29	Organic phenol extract compositions of peanut hull agricultural residues and method
FI129584B (en)	2022-05-13	Resin composition
US4201699A (en)	1980-05-06	Phenol-aldehyde resin composition containing pecan pith extract and an aldehyde
US3285805A (en)	1966-11-15	Polyvalent metal carbonate-extended phenolic resins
US4469858A (en)	1984-09-04	Tree foliage extracts and their use in phenol-aldehyde resins
Schroeder	1991	Method for recovering and using lignin in adhesive resins by extracting demethylated lignin
Liu	1996	Modified lignin-based phenolic adhesives for southern pine plywood and flakeboard
SE192921C1 (no)	1964-01-01