CA2214013A1 - Lignin based polyols - Google Patents
Lignin based polyolsInfo
- Publication number
- CA2214013A1 CA2214013A1 CA002214013A CA2214013A CA2214013A1 CA 2214013 A1 CA2214013 A1 CA 2214013A1 CA 002214013 A CA002214013 A CA 002214013A CA 2214013 A CA2214013 A CA 2214013A CA 2214013 A1 CA2214013 A1 CA 2214013A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- lignin
- polyol
- pulping process
- blend
- Prior art date
- 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.)
- Granted
Links
- 229920005610 lignin Polymers 0.000 title claims abstract 25
- 229920005862 polyol Polymers 0.000 title claims abstract 17
- 150000003077 polyols Chemical class 0.000 title claims abstract 17
- 238000000034 method Methods 0.000 claims abstract 7
- 238000004537 pulping Methods 0.000 claims abstract 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000006260 foam Substances 0.000 claims abstract 5
- 239000012948 isocyanate Substances 0.000 claims abstract 5
- 150000002513 isocyanates Chemical class 0.000 claims abstract 5
- 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 claims abstract 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract 4
- 239000011734 sodium Substances 0.000 claims abstract 4
- 239000004033 plastic Substances 0.000 claims abstract 3
- 229920003023 plastic Polymers 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 27
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims 4
- 229920000570 polyether Polymers 0.000 claims 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 3
- 229920001732 Lignosulfonate Polymers 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 2
- 238000000576 coating method Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000005031 sulfite paper Substances 0.000 claims 2
- 239000002028 Biomass Substances 0.000 claims 1
- 229920001131 Pulp (paper) Polymers 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000002655 kraft paper Substances 0.000 claims 1
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G1/00—Methods of preparing compounds of metals not covered by subclasses C01B, C01C, C01D, or C01F, in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6492—Lignin containing materials; Wood resins; Wood tars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Certain lignins which are readily available from pulping processes function as a polyol component of an isocyanate system to make foams and urethane plastics. Use of the lignin in this manner provides moisture and flame resistance and produces products having sufficient rigidity. The sodium level must be controlled so that the reaction between the hydroxyl groups and the isocyanates produces products with the optimal properties.
Claims (23)
1. A composition wherein lignin is blended with a polyol to produce a lignin polyol which is a mixture that can be readily reacted with isocyanates to produce a foam, plastic or other useable material.
2. A composition as in claim(1) wherein the polyether polyol that is used to blend with lignin contains between 1% and 100% ethylene oxide as one of its reactive materials.
3 . A composition as in claim (1) wherein mixtures of polyether polyols are used to blend with lignin.
4. A composition as in claim (1) wherein mixtures of polyether and polyester polyols are used to blend with lignin.
5. A composition as in claim (1) wherein mixtures of polyether polyols that contain amino groups are used to blend with lignin.
6. A composition as in claim (1) wherein the lignin that is used is from a solvent pulping process.
7. A composition as in claim (1) wherein the lignin that is used is from the kraft paper pulping process.
8. A composition as in claim (1) wherein the lignin is from a biomass process.
9. A composition as in claim (1) wherein the lignin is from a mechanical pulping process.
10. A composition as in claim (1) wherein the lignin is a lignosulfonate from the sulfite paper pulping process.
11. A composition as in claim (1) wherein the polyol is WL-440 (a polyol produced from ethylene oxide and propylene oxide).
12. A composition as in claim (1) wherein the polyol is WL-1590 ( a polyol produced from ethylene oxide and propylene oxide by Huntsman Chemical).
13. A composition as in claim (1) wherein the lignin is a lignosulfonate from the sulfite paper pulping process.
14. A composition as in claim (1) wherein the polyol is WL-400 ( a polyol produced from ethylene oxide and propylene oxide).
15. A composition as in claim (1) wherein the lignin is a lignin from a semi-mechanical pulp.
16. A composition as in claim (1) wherein the lignin that is used has preferably less than 2% ash level.
17. A Composition as in claim (1) wherein the lignin that is used has preferably less than 1% sodium.
18. A composition as in claim (1) wherein the lignin that is used has preferably less than 500 parts per million of sodium.
19. A composition as in claim (1) wherein the lignin preferably contains less than 2% water soluble ions.
20. A composition wherein lignin is added to a polyol to improve the moisture resistance of the resulting foam or urethane product.
21. A composition wherein lignin is added to the polyol system to improve the flame resistance of the urethane foam or urethane product.
22. A composition as in claim (1) wherein the sodium level is low enough so that the reaction rate of the isocyanate and hydroxyls group of the lignin based polyol is controllable enough to produce a useful product such as foam, plastic and coating.
23. A composition as in claim (1) wherein this lignin based polyol is blended with suitable solvents and mixed with the appropriate isocyanates to produce a urethane coating for a variety of substrates.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US952995P | 1995-12-29 | 1995-12-29 | |
| US60/009,529 | 1995-12-29 | ||
| PCT/US1996/020140 WO1997024362A1 (en) | 1995-12-29 | 1996-12-27 | Lignin based polyols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2214013A1 true CA2214013A1 (en) | 1997-07-10 |
| CA2214013C CA2214013C (en) | 2011-05-10 |
Family
ID=21738217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2214013A Expired - Lifetime CA2214013C (en) | 1995-12-29 | 1996-12-27 | Lignin based polyols |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0812326A4 (en) |
| JP (1) | JPH11501946A (en) |
| KR (1) | KR19980702567A (en) |
| CN (1) | CN1176643A (en) |
| AU (1) | AU1336497A (en) |
| BR (1) | BR9607058A (en) |
| CA (1) | CA2214013C (en) |
| EA (1) | EA199700204A1 (en) |
| MX (1) | MX9706348A (en) |
| NO (1) | NO973988L (en) |
| PL (1) | PL322023A1 (en) |
| SE (1) | SE9703037D0 (en) |
| WO (1) | WO1997024362A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011097719A1 (en) * | 2010-02-15 | 2011-08-18 | Lignol Innovations Ltd. | Binder compositions comprising lignin derivatives |
| US20120136097A1 (en) * | 2009-05-28 | 2012-05-31 | Alex Berlin | Resin compositions comprising lignin derivatives |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100469810C (en) * | 2001-06-15 | 2009-03-18 | 独立行政法人产业技术综合研究所 | Lignin-containing polyurethane and process for producing the same |
| ITTO20090351A1 (en) * | 2009-05-04 | 2010-11-05 | Univ Pisa | PROCEDURE FOR THE PRODUCTION OF POLYURETHANE / POLYUREIC FOAMS FROM LIGNINA-BASED MATERIALS |
| US8431635B2 (en) | 2009-05-28 | 2013-04-30 | Lignol Innovations Ltd. | Derivatives of native lignin from softwood feedstocks |
| JP2011219715A (en) * | 2010-02-10 | 2011-11-04 | Hitachi Chem Co Ltd | Resin compound material for molding |
| CA2798268C (en) | 2010-02-15 | 2019-02-12 | Lignol Innovations Ltd. | Carbon fibre compositions comprising lignin derivatives |
| CA2829413A1 (en) | 2011-03-24 | 2012-09-27 | Lignol Innovations Ltd. | Compositions comprising lignocellulosic biomass and organic solvent |
| EP2694456B1 (en) * | 2011-04-06 | 2017-01-04 | Harold E. Thompson | Multi-purpose lignin-carbohydrate binding system |
| WO2013113462A1 (en) * | 2012-02-02 | 2013-08-08 | Annikki Gmbh | Process for the production of polyols |
| JP2013170245A (en) * | 2012-02-22 | 2013-09-02 | Hitachi Chemical Co Ltd | Novel polyurethane |
| EP2644758B1 (en) * | 2012-03-29 | 2014-12-10 | Honda R&D Europe (Deutschland) GmbH | Stabilization of lignin carbon fibers with crosslinkers |
| JP2015519452A (en) * | 2012-06-01 | 2015-07-09 | ストラ エンソ オーワイジェイ | Dispersed composition containing lignin, process for its production and use thereof |
| CA2893088C (en) * | 2012-12-18 | 2020-10-20 | Akzo Nobel Coatings International B.V. | Lignin based coating compositions |
| CA2918686C (en) | 2013-08-13 | 2017-05-30 | Enerlab 2000 Inc. | Process for the preparation of lignin based polyurethane products |
| CN105622957B (en) * | 2014-11-05 | 2018-05-04 | 中国石油化工集团公司 | A kind of preparation method of lignin polyether polyalcohol |
| WO2016118411A1 (en) * | 2015-01-21 | 2016-07-28 | Resinate Materials Group, Inc. | High recycle content polyols from thermoplastic polyesters and lignin or tannin |
| CN105175682B (en) * | 2015-09-25 | 2017-11-14 | 南京工业大学 | Process for preparing polyurethane foam by using novel lignin liquefaction method |
| CN106283642B (en) * | 2016-08-09 | 2018-12-18 | 李挺晖 | A method of fire retardant is prepared using black liquid |
| KR20190045224A (en) * | 2016-08-23 | 2019-05-02 | 내션얼 리서치 카운슬 오브 캐나다 | Lignin pellets and methods for their preparation |
| CN111454465B (en) * | 2020-04-15 | 2022-05-24 | 黎明化工研究设计院有限责任公司 | Modified lignin, full-water-based low-density flame-retardant flexible polyurethane foam composition and preparation method thereof |
| CN111607062B (en) * | 2020-05-29 | 2022-04-08 | 河南恒泰源新材料有限公司 | Biomass polyurethane foam material and preparation method thereof |
| CN113142184A (en) * | 2021-04-08 | 2021-07-23 | 浙江海洋大学 | Method for manufacturing marine organism specimen for teaching |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3519581A (en) * | 1967-01-13 | 1970-07-07 | Westvaco Corp | Method of producing synthetic lignin-polyisocyanate resin |
| US4851457A (en) * | 1988-02-16 | 1989-07-25 | Kurple Kenneth R | Foundry resins |
| JP2675997B2 (en) * | 1988-05-16 | 1997-11-12 | 工業技術院長 | Novel polyurethane manufacturing method |
-
1996
- 1996-12-27 MX MX9706348A patent/MX9706348A/en active IP Right Grant
- 1996-12-27 AU AU13364/97A patent/AU1336497A/en not_active Abandoned
- 1996-12-27 WO PCT/US1996/020140 patent/WO1997024362A1/en not_active Application Discontinuation
- 1996-12-27 EA EA199700204A patent/EA199700204A1/en unknown
- 1996-12-27 KR KR1019970705973A patent/KR19980702567A/en not_active Application Discontinuation
- 1996-12-27 CN CN96192247A patent/CN1176643A/en active Pending
- 1996-12-27 JP JP9524388A patent/JPH11501946A/en active Pending
- 1996-12-27 PL PL96322023A patent/PL322023A1/en unknown
- 1996-12-27 EP EP96944852A patent/EP0812326A4/en not_active Ceased
- 1996-12-27 CA CA2214013A patent/CA2214013C/en not_active Expired - Lifetime
- 1996-12-27 BR BR9607058A patent/BR9607058A/en not_active Application Discontinuation
-
1997
- 1997-08-22 SE SE9703037A patent/SE9703037D0/en not_active Application Discontinuation
- 1997-08-29 NO NO973988A patent/NO973988L/en not_active Application Discontinuation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120136097A1 (en) * | 2009-05-28 | 2012-05-31 | Alex Berlin | Resin compositions comprising lignin derivatives |
| US9267027B2 (en) * | 2009-05-28 | 2016-02-23 | Fibria Innovations Inc. | Resin compositions comprising lignin derivatives |
| WO2011097719A1 (en) * | 2010-02-15 | 2011-08-18 | Lignol Innovations Ltd. | Binder compositions comprising lignin derivatives |
| US9505964B2 (en) | 2010-02-15 | 2016-11-29 | Fibria Innovations Inc. | Binder compositions comprising lignin derivatives |
| US9982174B2 (en) | 2010-02-15 | 2018-05-29 | Fibria Innovations Inc. | Binder compositions comprising lignin derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| NO973988D0 (en) | 1997-08-29 |
| SE9703037L (en) | 1997-08-22 |
| CN1176643A (en) | 1998-03-18 |
| PL322023A1 (en) | 1998-01-05 |
| EA199700204A1 (en) | 1998-02-26 |
| AU1336497A (en) | 1997-07-28 |
| SE9703037D0 (en) | 1997-08-22 |
| EP0812326A4 (en) | 1998-05-06 |
| JPH11501946A (en) | 1999-02-16 |
| EP0812326A1 (en) | 1997-12-17 |
| KR19980702567A (en) | 1998-07-15 |
| BR9607058A (en) | 1998-12-15 |
| CA2214013C (en) | 2011-05-10 |
| NO973988L (en) | 1997-10-28 |
| MX9706348A (en) | 1997-11-29 |
| WO1997024362A1 (en) | 1997-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20161228 |