WO1997024362A1 - Lignin based polyols - Google Patents

Lignin based polyols Download PDF

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Publication number
WO1997024362A1
WO1997024362A1 PCT/US1996/020140 US9620140W WO9724362A1 WO 1997024362 A1 WO1997024362 A1 WO 1997024362A1 US 9620140 W US9620140 W US 9620140W WO 9724362 A1 WO9724362 A1 WO 9724362A1
Authority
WO
WIPO (PCT)
Prior art keywords
lignin
composition
polyol
foam
pulping process
Prior art date
Application number
PCT/US1996/020140
Other languages
French (fr)
Inventor
Kenneth R. Kurple
Original Assignee
Kurple Kenneth R
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 Kurple Kenneth R filed Critical Kurple Kenneth R
Priority to JP9524388A priority Critical patent/JPH11501946A/en
Priority to EP96944852A priority patent/EP0812326A4/en
Priority to US08/913,565 priority patent/US6025452A/en
Priority to MX9706348A priority patent/MX9706348A/en
Priority to BR9607058A priority patent/BR9607058A/en
Priority to EA199700204A priority patent/EA199700204A1/en
Priority to AU13364/97A priority patent/AU1336497A/en
Priority to CA2214013A priority patent/CA2214013C/en
Publication of WO1997024362A1 publication Critical patent/WO1997024362A1/en
Priority to SE9703037A priority patent/SE9703037D0/en
Priority to NO973988A priority patent/NO973988L/en

Links

Classifications

    • 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
    • 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

Definitions

  • foams and urethane plastics are made by reacting a polyol with an isocyanate with a functionality of at least 2 (two) or greater.
  • the polyol can be a polyester molecule which has at least a functionality of at least 2 (two) or greater.
  • the polyol can also be a polyether polyol which is made by reacting propylene oxide or ethylene oxide with a molecule such as ethylene glycol or glycerine to produce molecules with various molecule weights, which have pendant hydroxyl groups which will react with difunctional or multifunctional isocyanates to produce a solid plastic or foam.
  • a polyether polyol which is made by reacting propylene oxide or ethylene oxide with a molecule such as ethylene glycol or glycerine to produce molecules with various molecule weights, which have pendant hydroxyl groups which will react with difunctional or multifunctional isocyanates to produce a solid plastic or foam.
  • a rigid foam or a urethane plastic it is necessary to react one part polyol with one part isocyanate. This is because the isocyanate generally contains aromatic rings and this is what makes the foam rigid, as well as having a high cross
  • a major disadvantage of these high levels of isocyanate is that when the foam is burned, high levels of toxic gases are produced which are generally derived from the isocyanate part of the molecule. It would be a tremendous advantage to be able to reduce the toxic fumes. It has been discovered that by using the lignin molecule as part of the polyol portion the significant advantages result. One is that by using the lignin molecule in the polyol portion of the system the amount of isocyanate can be reduced 40% or more and still produce rigid foam. This reduces the amount of toxic gases that are derived from the isocyanate portion of the system.
  • the lignin molecule is a natural phenolic type molecule that occurs in wood, straw, sugar cane and other natural materials.
  • lignin that is produced as a byproduct of the pulping process to make paper is just burned to recover heat value. In the United States alone over 50 billion pounds lignin are burned annually just for its heat value. Any lignin from the Kraft pulping process, sulfite pulping process, semi mechanical pulping process, thermomechanical pulping process, semi-chemical pulping process, solvent process, steam explosion pulping process and biomass pulping process can be used.
  • lignins can function quite well as a polyol component for an isocyanate system, these lignins can be used at different levels in the system depending on what fmal properties of the system are desired.
  • the use of the lignin molecule also significantly improves the moisture resistance of a foam, in fact when the proper level of lignin is used in a urethane foam the urethane foam will be almost impervious to moisture even when in direct contact with moisture.
  • Commercial foams made with the present polyols literally absorb moisture like a sponge.
  • Another major advantage of using lignin as a part of the polyol system is the flame resistance of the finished foam or urethane foam of urethane plastic part.
  • lignin acts as a natural flame retardant.
  • polyether polyol that is made from ethylene oxide. This is very important because when a regular polyether polyol is made from just propylene oxide the resulting polyol does not readily solubilize the lignin molecule and in many cases phase separation results and does not produce a quality urethane foam or plastic product.
  • ethylene oxide as a part of the polyol makes it possible to make these blends with lignin.
  • one of the major aspects of this invention is that in order to make high quality urethane foams and plastic materials the amount of sodium or other caustic ions such as potassium that are present in the lignin can have a dramatic affect on the properties of the final urethane product. This is because it is a well known fact that materials that produce a basic PH in water can perform as very strong catalysts for the isocyanate hydroxyl reaction that produces the urethane linkage. Therefore if the sodium level is too high it will cause the reaction between the hydroxyl groups and isocyanates go too fast which can produce a very poor quality product.
  • a suitable vessel use heat and or pressure to blend 300 parts of a lignin produced from a solvent pulping process and 700 parts of WL-440 (a polyether polyol that is made from a combination of propylene oxide and ethylene oxide) with agitation by using a suitable mixer and heat and higher pressure if necessary.
  • This mixture can be heated to 200° F. to improve the rate of solution, the mixing is continued until a dark solution results.
  • What results is a liquid material that has the following physical viscosity: 1532 centistrokes at 100° F. whose viscosity will depend on the particular lignin that is used.
  • thermosetting urethane part 1.5 parts of the resin solution of Example I is mixed with 1 part of Rubinate R1840 (an ICI product) and poured into a mold and allowed to harden. The mold can be heated as in a compression mold and this will produce a very hard tough plastic. The hardness of the product will depend on the particular lignin used.
  • Example III In order to produce a foam, 2 parts of the lignin based polyol of
  • Example I is premixed with 0.05 parts of water and 1 part Rubinate R1840 and then poured into a suitable container and a free rising foam will result.
  • Example IV is premixed with 0.05 parts of water and 1 part Rubinate R1840 and then poured into a suitable container and a free rising foam will result.
  • a blowing agent can be mixed with this lignin based polyol in example I. Therefore 2 parts of lignin based polyol of example I is premixed with 0.6 parts of Forane 141 b (1.1 dichloro- 1-fluroethane), then this mixture is mixed with 1 part of Rubinate R-1840 and then poured into a suitable container and a free rising foam low density will result.
  • Forane 141 b 1.1 dichloro- 1-fluroethane
  • one part of the lignin based polyol of example I is mixed with 1 part of suitable coating solvent depending on the coating application. Then this premix is mixed with 1 part Rubinate R-1840 and the resulting mixture is used to coat a variety of substances. The viscosity of this resulting mixture can be adjusted with suitable solvents depending on the final coating application.
  • Kraft lignin or other type lignin may be employed.

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.

Description

LIGNIN BASED POLYOLS
BACKGROUND OF THE INVENTION
At the present time foams and urethane plastics are made by reacting a polyol with an isocyanate with a functionality of at least 2 (two) or greater.
The polyol can be a polyester molecule which has at least a functionality of at least 2 (two) or greater. The polyol can also be a polyether polyol which is made by reacting propylene oxide or ethylene oxide with a molecule such as ethylene glycol or glycerine to produce molecules with various molecule weights, which have pendant hydroxyl groups which will react with difunctional or multifunctional isocyanates to produce a solid plastic or foam. However at present time in order to produce a rigid foam or a urethane plastic it is necessary to react one part polyol with one part isocyanate. This is because the isocyanate generally contains aromatic rings and this is what makes the foam rigid, as well as having a high crosslink density.
Also, a major disadvantage of these high levels of isocyanate is that when the foam is burned, high levels of toxic gases are produced which are generally derived from the isocyanate part of the molecule. It would be a tremendous advantage to be able to reduce the toxic fumes. It has been discovered that by using the lignin molecule as part of the polyol portion the significant advantages result. One is that by using the lignin molecule in the polyol portion of the system the amount of isocyanate can be reduced 40% or more and still produce rigid foam. This reduces the amount of toxic gases that are derived from the isocyanate portion of the system. The lignin molecule is a natural phenolic type molecule that occurs in wood, straw, sugar cane and other natural materials. Generally the majority of the lignin that is produced as a byproduct of the pulping process to make paper is just burned to recover heat value. In the United States alone over 50 billion pounds lignin are burned annually just for its heat value. Any lignin from the Kraft pulping process, sulfite pulping process, semi mechanical pulping process, thermomechanical pulping process, semi-chemical pulping process, solvent process, steam explosion pulping process and biomass pulping process can be used.
As part of this present invention it was discovered that certain lignins can function quite well as a polyol component for an isocyanate system, these lignins can be used at different levels in the system depending on what fmal properties of the system are desired. The use of the lignin molecule also significantly improves the moisture resistance of a foam, in fact when the proper level of lignin is used in a urethane foam the urethane foam will be almost impervious to moisture even when in direct contact with moisture. Commercial foams made with the present polyols literally absorb moisture like a sponge. Another major advantage of using lignin as a part of the polyol system is the flame resistance of the finished foam or urethane foam of urethane plastic part. This is because lignin acts as a natural flame retardant. However one of the major aspects of this invention is that the lignin molecule becomes readily soluble in polyether polyol that is made from ethylene oxide. This is very important because when a regular polyether polyol is made from just propylene oxide the resulting polyol does not readily solubilize the lignin molecule and in many cases phase separation results and does not produce a quality urethane foam or plastic product. We have found that ethylene oxide as a part of the polyol makes it possible to make these blends with lignin.
What has been discovered is that where current polyether polyols only have marginal solubility for various lignins this fact makes it very difficult to produce a high quality foam or urethane plastic part because the lignin will tend to phase separate when the isocyanate is added to the lignin polyol blend and this makes it very difficult to make consistent physical products.
Also one of the major aspects of this invention is that in order to make high quality urethane foams and plastic materials the amount of sodium or other caustic ions such as potassium that are present in the lignin can have a dramatic affect on the properties of the final urethane product. This is because it is a well known fact that materials that produce a basic PH in water can perform as very strong catalysts for the isocyanate hydroxyl reaction that produces the urethane linkage. Therefore if the sodium level is too high it will cause the reaction between the hydroxyl groups and isocyanates go too fast which can produce a very poor quality product. It was discovered and it is one of the major aspects of this invention to reduce the sodium level to levels that are low enough to make it possible to produce a useful product once the lignin based polyol has reacted with the isocyanate. Also high levels of sodium ions or other inorganic ions such as potassium will actually degrade the foam in time.
Example I
In a suitable vessel use heat and or pressure to blend 300 parts of a lignin produced from a solvent pulping process and 700 parts of WL-440 (a polyether polyol that is made from a combination of propylene oxide and ethylene oxide) with agitation by using a suitable mixer and heat and higher pressure if necessary. This mixture can be heated to 200° F. to improve the rate of solution, the mixing is continued until a dark solution results. What results is a liquid material that has the following physical viscosity: 1532 centistrokes at 100° F. whose viscosity will depend on the particular lignin that is used.
Example II
In order to make a thermosetting urethane part, 1.5 parts of the resin solution of Example I is mixed with 1 part of Rubinate R1840 (an ICI product) and poured into a mold and allowed to harden. The mold can be heated as in a compression mold and this will produce a very hard tough plastic. The hardness of the product will depend on the particular lignin used. Example III In order to produce a foam, 2 parts of the lignin based polyol of
Example I is premixed with 0.05 parts of water and 1 part Rubinate R1840 and then poured into a suitable container and a free rising foam will result. Example IV
In order to produce a low density foam, a blowing agent can be mixed with this lignin based polyol in example I. Therefore 2 parts of lignin based polyol of example I is premixed with 0.6 parts of Forane 141 b (1.1 dichloro- 1-fluroethane), then this mixture is mixed with 1 part of Rubinate R-1840 and then poured into a suitable container and a free rising foam low density will result. Example V
In order to make a urethane coating based on the lignin based polyol of example I, one part of the lignin based polyol of example I is mixed with 1 part of suitable coating solvent depending on the coating application. Then this premix is mixed with 1 part Rubinate R-1840 and the resulting mixture is used to coat a variety of substances. The viscosity of this resulting mixture can be adjusted with suitable solvents depending on the final coating application.
It is understood to those skilled in the art that Kraft lignin or other type lignin may be employed.

Claims

What is claimed is:
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(l) 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 mat 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.
PCT/US1996/020140 1995-12-29 1996-12-27 Lignin based polyols WO1997024362A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP9524388A JPH11501946A (en) 1995-12-29 1996-12-27 Lignin based polyols
EP96944852A EP0812326A4 (en) 1995-12-29 1996-12-27 Lignin based polyols
US08/913,565 US6025452A (en) 1996-12-27 1996-12-27 Lignin based polyols
MX9706348A MX9706348A (en) 1995-12-29 1996-12-27 Lignin based polyols.
BR9607058A BR9607058A (en) 1995-12-29 1996-12-27 Composition
EA199700204A EA199700204A1 (en) 1995-12-29 1996-12-27 COMPOSITION FOR OBTAINING FOAM, PLASTIC AND OTHER MATERIALS
AU13364/97A AU1336497A (en) 1995-12-29 1996-12-27 Lignin based polyols
CA2214013A CA2214013C (en) 1995-12-29 1996-12-27 Lignin based polyols
SE9703037A SE9703037D0 (en) 1995-12-29 1997-08-22 Lignin-based polyols
NO973988A NO973988L (en) 1995-12-29 1997-08-29 Lignin-based polyols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US952995P 1995-12-29 1995-12-29
US60/009,529 1995-12-29

Publications (1)

Publication Number Publication Date
WO1997024362A1 true WO1997024362A1 (en) 1997-07-10

Family

ID=21738217

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/020140 WO1997024362A1 (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 (9)

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WO2002102873A1 (en) * 2001-06-15 2002-12-27 National Institute Of Advanced Industrial Science And Technology 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
WO2013113462A1 (en) * 2012-02-02 2013-08-08 Annikki Gmbh Process for the production of polyols
EP2644758A1 (en) * 2012-03-29 2013-10-02 Honda R&D Europe (Deutschland) GmbH Stabilization of lignin carbon fibers with crosslinkers
EP2694456A1 (en) * 2011-04-06 2014-02-12 Harold E. Thompson Multi-purpose lignin-carbohydrate binding system
CN105175682A (en) * 2015-09-25 2015-12-23 南京工业大学 Technology for preparing polyurethane foam through novel lignin liquidation method
WO2016118411A1 (en) * 2015-01-21 2016-07-28 Resinate Materials Group, Inc. High recycle content polyols from thermoplastic polyesters and lignin or tannin
US9598529B2 (en) 2013-08-13 2017-03-21 Enerlab 2000 Inc. Process for the preparation of lignin based polyurethane products
CN113142184A (en) * 2021-04-08 2021-07-23 浙江海洋大学 Method for manufacturing marine organism specimen for teaching

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EP2435457B1 (en) * 2009-05-28 2020-02-19 Suzano Canada Inc. Resin compositions comprising lignin derivatives
EP2435453B1 (en) 2009-05-28 2022-03-02 Suzano Canada Inc. Derivatives of native lignin
JP2011219715A (en) * 2010-02-10 2011-11-04 Hitachi Chem Co Ltd Resin compound material for molding
CN102959033B (en) * 2010-02-15 2016-10-12 丽格诺新创有限公司 Adhesive composition containing modified lignin
CA2798268C (en) 2010-02-15 2019-02-12 Lignol Innovations Ltd. Carbon fibre compositions comprising lignin derivatives
CN103459511A (en) 2011-03-24 2013-12-18 丽格诺创新有限公司 Compositions comprising lignocellulosic biomass and organic solvent
JP2013170245A (en) * 2012-02-22 2013-09-02 Hitachi Chemical Co Ltd Novel polyurethane
RU2637027C2 (en) * 2012-06-01 2017-11-29 Стора Энсо Ойй Composition as content of lignin dispersion, method of its manufacture and use
EP2935411B1 (en) * 2012-12-18 2019-04-24 Akzo Nobel Coatings International B.V. Lignin based coating compositions
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
CN106283642B (en) * 2016-08-09 2018-12-18 李挺晖 A method of fire retardant is prepared using black liquid
US20200131318A1 (en) * 2016-08-23 2020-04-30 National Research Council Of Canada Lignin pellets and process for producing same
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

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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
WO2002102873A1 (en) * 2001-06-15 2002-12-27 National Institute Of Advanced Industrial Science And Technology 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
EP2694456A1 (en) * 2011-04-06 2014-02-12 Harold E. Thompson Multi-purpose lignin-carbohydrate binding system
EP2694456A4 (en) * 2011-04-06 2015-04-29 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
EP2644758A1 (en) * 2012-03-29 2013-10-02 Honda R&D Europe (Deutschland) GmbH Stabilization of lignin carbon fibers with crosslinkers
US9598529B2 (en) 2013-08-13 2017-03-21 Enerlab 2000 Inc. Process for the preparation of lignin based polyurethane products
WO2016118411A1 (en) * 2015-01-21 2016-07-28 Resinate Materials Group, Inc. High recycle content polyols from thermoplastic polyesters and lignin or tannin
US9481760B2 (en) 2015-01-21 2016-11-01 Resinate Materials Group, Inc. High recycle content polyols from thermoplastic polyesters and lignin or tannin
US9751978B2 (en) 2015-01-21 2017-09-05 Resinate Materials Group, Inc. High recycle content polyols from thermoplastic polyesters and lignin or tannin
US9988489B2 (en) 2015-01-21 2018-06-05 Resinate Materials Group, Inc. High recycle content polyols from thermoplastic polyesters and lignin or tannin
CN105175682A (en) * 2015-09-25 2015-12-23 南京工业大学 Technology for preparing polyurethane foam through novel lignin liquidation method
CN105175682B (en) * 2015-09-25 2017-11-14 南京工业大学 A kind of technique for preparing polyurethane foam using the new liquifying method of lignin
CN113142184A (en) * 2021-04-08 2021-07-23 浙江海洋大学 Method for manufacturing marine organism specimen for teaching

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AU1336497A (en) 1997-07-28
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NO973988L (en) 1997-10-28
SE9703037L (en) 1997-08-22
CA2214013A1 (en) 1997-07-10
SE9703037D0 (en) 1997-08-22
EP0812326A1 (en) 1997-12-17
JPH11501946A (en) 1999-02-16
EA199700204A1 (en) 1998-02-26
BR9607058A (en) 1998-12-15
CA2214013C (en) 2011-05-10
CN1176643A (en) 1998-03-18
EP0812326A4 (en) 1998-05-06

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