EP0920477A1 - Modified lignins - Google Patents

Modified lignins

Info

Publication number
EP0920477A1
EP0920477A1 EP97938638A EP97938638A EP0920477A1 EP 0920477 A1 EP0920477 A1 EP 0920477A1 EP 97938638 A EP97938638 A EP 97938638A EP 97938638 A EP97938638 A EP 97938638A EP 0920477 A1 EP0920477 A1 EP 0920477A1
Authority
EP
European Patent Office
Prior art keywords
lignin
melt
composition
flow characteristics
polyether
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.)
Withdrawn
Application number
EP97938638A
Other languages
German (de)
French (fr)
Other versions
EP0920477A4 (en
Inventor
Kenneth R. Kurple
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP0920477A1 publication Critical patent/EP0920477A1/en
Publication of EP0920477A4 publication Critical patent/EP0920477A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00Compositions of lignin-containing materials
    • C08L97/005Lignin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07GCOMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G99/00Subject matter not provided for in other groups of this subclass
    • C07G99/002Compounds of unknown constitution containing sulfur
    • C07G99/0022Compounds of unknown constitution containing sulfur derived from hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02Polyalkylene oxides

Definitions

  • lignins There are substantial markets available to lignins if they can achieve the same melt and flow characteristics as a phenolic resin. There are at least two major factors of this present invention which allow these new modified lignins to be able to totally replace phenolic resins.
  • the first factor that has been that a lignin which does not have any distinct melt point or flow characteristics can be modified with a certain amount of polyether glycol to achieve a certain desired melt point. So, what occurs is a certain ratio of lignin to a polyether compound (such as polyether glycol) produces a product which has a distinct melt point and melt viscosity. This effect can be thought of as a type of plasticizing effect wherein the lignin can be thought of as the hard resin.
  • lignin is derived from wood, which is a natural product. As in all natural products there will exist a certain amount of variation depending on the exact type of wood, age and other conditions. These variations are another major reason why lignins have not been extensively utilized as replacements for phenolic resins, whereas a synthetic phenolic resin can be made to exact and reproducible specifications, and the lignin molecule may have wide variations. Therefore, if there is a variation in the lignin this can be adjusted by changing the ratio of lignin to a polyether compound (such as polyether glycol) in order to achieve the desired melt and flow characteristics.
  • a polyether compound such as polyether glycol
  • lignins are a natural product and as such there may be natural chemical variations in the lignin molecule. These variations may include different functional groups or different concentrations of these functional groups. These variations become rather significant when you are trying to formulate a product that must have, in addition to certain physical properties such as melt and flow, certain curing characteristics in order to produce a consistent product day in and day out.
  • lignins can be used as either partial or total replacement of phenolic resins in phenolic production.
  • One major advantage is that lignins can offer significant economic advantages. Since most phenolic resins are made from phenol and phenol is a petrochemical product, cost of phenol is very dependent on the cost of oil. So, as the cost of oil increases, the cost of phenol and phenolic resins will also increase. These price increases could make phenolic resins less competitive and thereby make it possible for these phenolic products to be replaced by other products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

Ligning and polyether glycol produces a product which has a distinct melt point and melt viscosity. This has a plasticizing effect wherein the polyether glycol can be thought of as the hard resin. When 20 parts of polyether glycol are processed with 80 parts of lignin a new material which has a melt point and a viscosity is created whereas lignin itself has no melt and flow characteristics. The new modified lignin can be cured with hexamine like a phenolic resin.

Description

MODIFIED LIGNINS
There are substantial markets available to lignins if they can achieve the same melt and flow characteristics as a phenolic resin. There are at least two major factors of this present invention which allow these new modified lignins to be able to totally replace phenolic resins. The first factor that has been that a lignin which does not have any distinct melt point or flow characteristics can be modified with a certain amount of polyether glycol to achieve a certain desired melt point. So, what occurs is a certain ratio of lignin to a polyether compound (such as polyether glycol) produces a product which has a distinct melt point and melt viscosity. This effect can be thought of as a type of plasticizing effect wherein the lignin can be thought of as the hard resin. For example, when 20- parts of a polyether glycol is properly processed with 80 parts of lignin what results is a new material which now has melt and flow characteristics, whereas lignin by itself has no melt and flow characteristics. Because these melt and flow characteristics are similar to a phenolic resin these new modified lignins can be cured with hexamine just like a phenolic resin. This is because the lignin molecule contains phenolic groups which are reactive to hexamine just as in a phenolic resin. This is significant because although lignin itself does contain phenolic groups that are reactive to hexamine the fact that the lignin molecule does not melt and flow means that it would be almost impossible to obtain a commercially moldable part from a press with heat and pressure.
.Another major advantage of this present invention is that lignin is derived from wood, which is a natural product. As in all natural products there will exist a certain amount of variation depending on the exact type of wood, age and other conditions. These variations are another major reason why lignins have not been extensively utilized as replacements for phenolic resins, whereas a synthetic phenolic resin can be made to exact and reproducible specifications, and the lignin molecule may have wide variations. Therefore, if there is a variation in the lignin this can be adjusted by changing the ratio of lignin to a polyether compound (such as polyether glycol) in order to achieve the desired melt and flow characteristics. Mother important aspect of this invention that has a synergisric effect on the melt and flow characteristics is the sodium level of the lignin. It was discovered that if the sodium level is too high the modified lignin will not have melt and flow characteristics which can be utilized as a commercial product. It was found that the same lignin, but with different sodium levels, will produce modified lignins with wide variations in melt and flow characteristics. Therefore, it was discovered that there is a certain critical level for the presence of sodium and other ionic materials above which no useful products could be obtained. This critical level may vary depending on the specific nature or chemical composition of the lignins. .Another major invention is the fact that lignins are a natural product and as such there may be natural chemical variations in the lignin molecule. These variations may include different functional groups or different concentrations of these functional groups. These variations become rather significant when you are trying to formulate a product that must have, in addition to certain physical properties such as melt and flow, certain curing characteristics in order to produce a consistent product day in and day out.
These curing characteristics are very important because in addition to the physical properties of the product they also determine the productivity, which directly affects how profitable the product will be. One major market for lignins is to either partially or totally replace phenolic resins in many products that currently use all phenolic resins. There are at least two major advantages why lignins can be used as either partial or total replacement of phenolic resins in phenolic production. One major advantage is that lignins can offer significant economic advantages. Since most phenolic resins are made from phenol and phenol is a petrochemical product, cost of phenol is very dependent on the cost of oil. So, as the cost of oil increases, the cost of phenol and phenolic resins will also increase. These price increases could make phenolic resins less competitive and thereby make it possible for these phenolic products to be replaced by other products.
Therefore, when more lignin can be incorporated into a phenolic product, this could offset price increases and make these lignin modified phenolic products more profitable and more competitive, thus increasing their market share.
EXAMPLE 1 In a suitable vessel 20 parts of Pluracol P-410 is heated to
200 °F and 80 parts of lignin is slowly added while adequate agitation is maintained and the heat slowly increased to 270 °F. The viscosity of this mixture will increase significantly but it still is able to be mixed. Then once all of the lignin is added, the mixture is continued to be mixed until everything is homogeneous. Then this mixture is poured out on to a surface which allows this mixture to cool and form a hard brittle material. This lignin is now in a form which is very similar to phenolic resins. This modification of the lignin now makes it possible for it to have melt and flow characteristics.

Claims

WHAT IS CLAIMED IS:
1. A composition comprising lignin blended with a polyether compound to improve the melt and flow characteristics of the lignin.
2. A composition as claimed in claim 1 wherein the ratio of said polyether compound to lignin is from 1% to 70%.
3. A composition comprising lignin blended with a polyester compound to improve the melt and flow characteristics of the lignin.
4. A composition as claimed in claim 3 wherein the ratio of said polyester compound to lignin is from 1% to 70%.
5. A composition as claimed in claim 1 wherein said polyether compound is produced by the reaction product of ethylene oxide and propylene oxide.
6. A composition comprising a combination of polyester resins and polyether glycols are blended to improve the melt and flow characteristics of the lignin.
7. A composition comprising a polyether derivative (reaction product of ethylene oxide and propylene oxide) selected from the group of nonylphenol, phenol or a substituted phenol blended with lignin to improve the melt and flow characteristics of lignin.
8. A composition as claimed in claim 1 wherein the sodium level of the ligrun in claim 1 is preferably below 22% by weight of sodium.
9. A composition as claimed in claim 1 wherein the modified lignin is reacted with hexamine to produce a cured product.
EP97938638A 1996-08-26 1997-08-26 Modified lignins Withdrawn EP0920477A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US2455896P 1996-08-26 1996-08-26
US24558P 1996-08-26
PCT/US1997/015039 WO1998008903A1 (en) 1996-08-26 1997-08-26 Modified lignins

Publications (2)

Publication Number Publication Date
EP0920477A1 true EP0920477A1 (en) 1999-06-09
EP0920477A4 EP0920477A4 (en) 1999-10-06

Family

ID=21821209

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97938638A Withdrawn EP0920477A4 (en) 1996-08-26 1997-08-26 Modified lignins

Country Status (5)

Country Link
EP (1) EP0920477A4 (en)
JP (1) JP2000517362A (en)
AU (1) AU4092497A (en)
CA (1) CA2262940C (en)
WO (1) WO1998008903A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6172204B1 (en) * 1999-06-04 2001-01-09 Regents Of The University Of Minnesota Compositions based on lignin derivatives
CN101265364B (en) * 2007-07-27 2010-08-11 张国栋 Thermoset plastics infiltration strengthened powdery plant fiber material and preparation method thereof
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
JP2019526694A (en) * 2016-08-23 2019-09-19 ナショナル リサーチ カウンシル オブ カナダ Lignin pellet and method for producing the same

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2192030A (en) * 1935-12-12 1940-02-27 Gen Electric Process for the manufacture of a lignin-containing press mass
US2156160A (en) * 1938-05-17 1939-04-25 Northwood Chemical Company Lignin molding compound
US3355400A (en) * 1960-09-26 1967-11-28 Union Carbide Corp Polyether-lignin compositions
US4833182A (en) * 1986-09-29 1989-05-23 Jim Walter Research Corp. Isocyanate-polyester polyol binder for manufacture of cellulosic composites
US5025046A (en) * 1989-12-15 1991-06-18 Kimberly-Clark Corporation Creping adhesive composition
ATE136317T1 (en) * 1991-11-07 1996-04-15 Ruetgerswerke Ag LIGNIN-MODIFIED BINDER MIXTURES AND METHOD FOR THE PRODUCTION THEREOF
US5614564A (en) * 1993-07-28 1997-03-25 Samsung General Chemicals Co., Ltd. Degradable foam and the method for its production

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No further relevant documents disclosed *
See also references of WO9808903A1 *

Also Published As

Publication number Publication date
JP2000517362A (en) 2000-12-26
AU4092497A (en) 1998-03-19
EP0920477A4 (en) 1999-10-06
WO1998008903A1 (en) 1998-03-05
CA2262940A1 (en) 1998-03-05
CA2262940C (en) 2003-11-04

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