CA2242554A1 - Lignin-based friction material - Google Patents
Lignin-based friction material Download PDFInfo
- Publication number
- CA2242554A1 CA2242554A1 CA002242554A CA2242554A CA2242554A1 CA 2242554 A1 CA2242554 A1 CA 2242554A1 CA 002242554 A CA002242554 A CA 002242554A CA 2242554 A CA2242554 A CA 2242554A CA 2242554 A1 CA2242554 A1 CA 2242554A1
- Authority
- CA
- Canada
- Prior art keywords
- lignin
- friction material
- material composition
- friction
- phenolic resin
- 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.)
- Abandoned
Links
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/025—Compositions based on an organic binder
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/021—Composition of linings ; Methods of manufacturing containing asbestos
- F16D69/022—Composition of linings ; Methods of manufacturing containing asbestos in the form of fibres
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D2200/00—Materials; Production methods therefor
- F16D2200/006—Materials; Production methods therefor containing fibres or particles
- F16D2200/0065—Inorganic, e.g. non-asbestos mineral fibres
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D2200/00—Materials; Production methods therefor
- F16D2200/006—Materials; Production methods therefor containing fibres or particles
- F16D2200/0073—Materials; Production methods therefor containing fibres or particles having lubricating properties
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Braking Arrangements (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
This invention provides for a friction material composition suitable for friction element formulation. The composition comprises an essentially sulfurfree lignin with low water solubility. The lignin replaces from about 1 to about 30 % on a weight basis with the phenolic resin in the friction material composition. A method of reducing noise within the range of human hearing resulting from friction element performance is also provided.
Description
CA 02242~4 1998-04-17 LIGNIN-BASED FRICTION MATERIAL
BACKGROIJND OF 1~ lNvl~;NlIoN
When the brakes of a vehicle are applied, the brake lining on each wheel frictionally engages another member to reduce the rotary motion o~ the wheel. During the ~rictional engagement, thermal energy is created as the drum or disc slide on the brake lining. Conventional organic brake linings are made up o~ a mixture of asbestos or steel ~ibers and modi~iers held together in a ~ixed matrix created by a phenolic resin The asbestos or steel fibers remain stable when subjected to thermal changes up to 800~ F. However, asbestos deteriorates at higher temperatures due to loss of water. When asbestos dehydrates, it is trans~ormed into ~orsterites or olivine while the phenolic resin is reduced to a carbonaceous resin as the matrix engages the drum or disc. However, when a phenolic resin is utilized, a melting of the phenolic resin at the surfaces o~ all particles occurs to wet the same and reduce the wear of the ~riction producing elements. Upon curing the phenolic resin reestablishes the matrix bond which holds the ~riction modifiers and asbestos in a ~ixed relationship.
Phenolic resins are produced through the conA~n~ation of a phenol with ~ormaldehyde in the presence o~ a catalyst. Phenol is derived ~rom benzene and the supply o~ benzene has been reduced because of industry changes. Because o~ the reduction in the supply o~ phenol and the elevated price o~ phenol, it has been a necessity to find an extender or substitute ~or phenolic resin.
In view of the ~oregoing, it was suggested that lignin or a lignin derivative be combined with a phenolic resin to produce a ~ixed matrix In U.S Patent No.
4,239,666 it is disclosed a composition ~or a ~riction material ~or use in Friction elements such as brake pads, CA 02242~4 1998-04-17 W097/14747 PCT~S95/13286 brake linings and clutch facings. In the friction material, lignosulfonate or kraft lignin are substituted for a portion of the phenolic resin binder However, such a combination presented severe limitations since the resulting friction elements emitted sulfur-based odors upon normal use and erratic brake performance.
The choice of lignin or lignin derivative that can be combined in friction material is greatly affected by the environmental considerations which affect the development of pulping technologies Due to increasing environmental demands during the last three decades, traditional sulfite pulping has almost completely been replaced by the kraft pulping process. Both sulfite and kraft pulping processes are noted for their contribution to air and water pollution, which requires costly pollution control equipment to bring kraft and sulfite pulping operations into environmental compliance. These pulping technologies can now be economically replaced by more environmentally friendly processes. One of these 20 prOCesseS i8 the organosolv pulping process which has ~;n;m~l impact on the environment. Unlike the traditional sulfite process, the organosolv process allows for the recovery of a highly pure, essentially sulfur-free and hydrophobic form of lignin with low water solubility.
This lignin can be suitable for the preparation of a lignin-based friction material for use in friction elements.
By the method o~ the present invention is provided an environmentally friendly lignin-based friction material composition. The composition when formulated in friction elements can greatly reduce the noise, wear and sulfur-based emissions which are generally encountered with prior art friction elements.
CA 02242~4 1998-04-17 WO97/14747 PCT~S95/13286 SUMMARY OF THE INVENTION
The invention provides for a friction material composition for use in friction element~ wherein an essentially sulfur-free lignin low water solubility replaces from about 1~ to about 30~ of the phenolic resin in the composition. The friction material composition when formulated into friction elements such as brake pads results in a significant reduction in wear, noise level, and sulfur-based emissions resulting ~rom the performance of the friction element.
Novel features and aspects of the invention, as well as other benefits will be readily ascertained from the more detailed description and claims which follow.
DESCRIPTION OF THE FIGURES
Figures 1 and 2 show the effect of 20~ lignin replacement on the uniformity of the coefficient of friction of the resulting brake pad as a function of temperature.
Figures 3 and 4 show the effect of 20~ lignin replacement on the noise performance of the resulting brake pad at different frequencies.
DESCRIPTION OF THE PREFERRED EMBODIMENT
This invention provides ~or a friction material composition having stability in the thermal operating range of most vehicle ~riction elements. The friction material composition when used in ~riction elements such CA 02242~4 1998-04-17 brake pads reduces noise levels and improves the wear of the friction element. The friction material composition comprises a highly pure, essentially sulfur-free and hydrophobic form of lignin with low water solubility at neutral or acidic pH.
A lignin which can be combined into the friction material can be selected from steam explosion, autohydrolysis extraction or soda lignins A preferred lignin to accomplish the objectives of this invention is lO the lignin described in U.S Patent No. 4,764,596. Such a lignin is a high purity organosolv lignin and is separated as a coproduct of the pulping and chemical delignification o~ plant biomass with organic solvents, for example ethanol. This lignin is an essentially sulfur-i~ree powder.
15 It has low water solubility at neutral or acidic pH and is soluble in aqueous alkali and selected organic solvents.
It is generally characterized by its hydrophobicity, high purity, melt flow and a low level of carbohydrates and inorganic cont~m;n~nts.
In a preferred embodiment, organosolv lignin can be used as a partial replacement ~or the phenol-formaldehyde resin binder used in friction material formulations wherein powder phenol-formaldehyde resin is used. Lignin can be formulated to replace on a weight 25 basis from about l to about 30~ of the phenolic resin. An example of such a friction material formulation comprises from about 20~ to about 35~ iron powder, from about O.l~
to about l.5~ hexamethylene tetramine, from about lO~ to about 15~ steel fiber or asbestos, from about 8~ to about 30 14~ phenolic resin, from about 7~ to about ll~ graphite and the balance is a modifier which comprises friction coe~ficient modifiers such as barium sul~ate, aluminum oxide and in certain ~ormulations, brown or black organic particles. Such a :Eormulation can comprise lignin o~ ~rom 35 about 0 08~ to about 4.2~ on a weight basis with the resulting ~riction material composition.
CA 02242~4 1998-04-17 WO97/14747 PCT~S95/13286 An important property of the lignin-based friction material composition of this invention is its water solubility. It has been observed that the water solubility of a friction material composition comprising a lignosulfonate shows a tenfold increase in water solubility as compared to a friction material composition comprising the same level of substitution with organosolv lignin. This observation can be explained by the fact that the lignosulfonate-based friction material composition has not been incorporated into the phenolic matrix to the same extent as the lignin of this invention.
Brake pads are manufactured by blending the friction material composition and then pressing the blend at from about 375~F to about 500~F for from about 10 minutes to about 45 minutes and at a pressure of from about 350 psig to about 750 psig. Manufacturing techniques are well known in the art.
In order to evaluate the friction material composition, a series of tests were performed on friction elements such as brake pads comprising the lignin of the invention. The pads were all formed by techniques well known in the art.
Figures 1 and 2 show that replacing 20~ of the phenolic resin with organosolv lignin did not affect the stability of the coefficient of friction as the temperature was changed. A stable coefficient of friction is a requirement of friction element products since drivers require the same braking power or feel regardless of the temperature of the friction elements.
The friction material composition of this invention when formulated in brake pads result in an improvement in wear characteristics (Table 1) CA 02242~4 1998-04-17 Table 1 Inner Outer Average (mm/qm of brake ~ad) Control 0.102 0.142 0.122 10~ Lignin 0.071 0.122 0.096 20~ Lignin 0.090 0.139 0.114 A reduction of oryanic deposits on the rotor can also be observed resulting in an improvement in vibration characteristics as confirmed by noise data as shown in Figure 4 (20~ lignin) as compared to Figure 3 (control).
The use of the lignin in brake pad formulations were tested at about 300 rpm, 50 psig and 300~F according to a modified Ford Test. Figure 4 demonstrates a shift of the peak of the frequency to the (hllm~n) non-audible part of the spectrum (approximately above 16 KHz).
The invention and many of its attendant advantages will be understood from the foregoing description, and it will be apparent that various modifications and changes can be made without departing from the spirit and scope of the invention or sacrificing all of its material advantages, the compositions and processes hereinbe~ore described being merely preferred embodiments.
BACKGROIJND OF 1~ lNvl~;NlIoN
When the brakes of a vehicle are applied, the brake lining on each wheel frictionally engages another member to reduce the rotary motion o~ the wheel. During the ~rictional engagement, thermal energy is created as the drum or disc slide on the brake lining. Conventional organic brake linings are made up o~ a mixture of asbestos or steel ~ibers and modi~iers held together in a ~ixed matrix created by a phenolic resin The asbestos or steel fibers remain stable when subjected to thermal changes up to 800~ F. However, asbestos deteriorates at higher temperatures due to loss of water. When asbestos dehydrates, it is trans~ormed into ~orsterites or olivine while the phenolic resin is reduced to a carbonaceous resin as the matrix engages the drum or disc. However, when a phenolic resin is utilized, a melting of the phenolic resin at the surfaces o~ all particles occurs to wet the same and reduce the wear of the ~riction producing elements. Upon curing the phenolic resin reestablishes the matrix bond which holds the ~riction modifiers and asbestos in a ~ixed relationship.
Phenolic resins are produced through the conA~n~ation of a phenol with ~ormaldehyde in the presence o~ a catalyst. Phenol is derived ~rom benzene and the supply o~ benzene has been reduced because of industry changes. Because o~ the reduction in the supply o~ phenol and the elevated price o~ phenol, it has been a necessity to find an extender or substitute ~or phenolic resin.
In view of the ~oregoing, it was suggested that lignin or a lignin derivative be combined with a phenolic resin to produce a ~ixed matrix In U.S Patent No.
4,239,666 it is disclosed a composition ~or a ~riction material ~or use in Friction elements such as brake pads, CA 02242~4 1998-04-17 W097/14747 PCT~S95/13286 brake linings and clutch facings. In the friction material, lignosulfonate or kraft lignin are substituted for a portion of the phenolic resin binder However, such a combination presented severe limitations since the resulting friction elements emitted sulfur-based odors upon normal use and erratic brake performance.
The choice of lignin or lignin derivative that can be combined in friction material is greatly affected by the environmental considerations which affect the development of pulping technologies Due to increasing environmental demands during the last three decades, traditional sulfite pulping has almost completely been replaced by the kraft pulping process. Both sulfite and kraft pulping processes are noted for their contribution to air and water pollution, which requires costly pollution control equipment to bring kraft and sulfite pulping operations into environmental compliance. These pulping technologies can now be economically replaced by more environmentally friendly processes. One of these 20 prOCesseS i8 the organosolv pulping process which has ~;n;m~l impact on the environment. Unlike the traditional sulfite process, the organosolv process allows for the recovery of a highly pure, essentially sulfur-free and hydrophobic form of lignin with low water solubility.
This lignin can be suitable for the preparation of a lignin-based friction material for use in friction elements.
By the method o~ the present invention is provided an environmentally friendly lignin-based friction material composition. The composition when formulated in friction elements can greatly reduce the noise, wear and sulfur-based emissions which are generally encountered with prior art friction elements.
CA 02242~4 1998-04-17 WO97/14747 PCT~S95/13286 SUMMARY OF THE INVENTION
The invention provides for a friction material composition for use in friction element~ wherein an essentially sulfur-free lignin low water solubility replaces from about 1~ to about 30~ of the phenolic resin in the composition. The friction material composition when formulated into friction elements such as brake pads results in a significant reduction in wear, noise level, and sulfur-based emissions resulting ~rom the performance of the friction element.
Novel features and aspects of the invention, as well as other benefits will be readily ascertained from the more detailed description and claims which follow.
DESCRIPTION OF THE FIGURES
Figures 1 and 2 show the effect of 20~ lignin replacement on the uniformity of the coefficient of friction of the resulting brake pad as a function of temperature.
Figures 3 and 4 show the effect of 20~ lignin replacement on the noise performance of the resulting brake pad at different frequencies.
DESCRIPTION OF THE PREFERRED EMBODIMENT
This invention provides ~or a friction material composition having stability in the thermal operating range of most vehicle ~riction elements. The friction material composition when used in ~riction elements such CA 02242~4 1998-04-17 brake pads reduces noise levels and improves the wear of the friction element. The friction material composition comprises a highly pure, essentially sulfur-free and hydrophobic form of lignin with low water solubility at neutral or acidic pH.
A lignin which can be combined into the friction material can be selected from steam explosion, autohydrolysis extraction or soda lignins A preferred lignin to accomplish the objectives of this invention is lO the lignin described in U.S Patent No. 4,764,596. Such a lignin is a high purity organosolv lignin and is separated as a coproduct of the pulping and chemical delignification o~ plant biomass with organic solvents, for example ethanol. This lignin is an essentially sulfur-i~ree powder.
15 It has low water solubility at neutral or acidic pH and is soluble in aqueous alkali and selected organic solvents.
It is generally characterized by its hydrophobicity, high purity, melt flow and a low level of carbohydrates and inorganic cont~m;n~nts.
In a preferred embodiment, organosolv lignin can be used as a partial replacement ~or the phenol-formaldehyde resin binder used in friction material formulations wherein powder phenol-formaldehyde resin is used. Lignin can be formulated to replace on a weight 25 basis from about l to about 30~ of the phenolic resin. An example of such a friction material formulation comprises from about 20~ to about 35~ iron powder, from about O.l~
to about l.5~ hexamethylene tetramine, from about lO~ to about 15~ steel fiber or asbestos, from about 8~ to about 30 14~ phenolic resin, from about 7~ to about ll~ graphite and the balance is a modifier which comprises friction coe~ficient modifiers such as barium sul~ate, aluminum oxide and in certain ~ormulations, brown or black organic particles. Such a :Eormulation can comprise lignin o~ ~rom 35 about 0 08~ to about 4.2~ on a weight basis with the resulting ~riction material composition.
CA 02242~4 1998-04-17 WO97/14747 PCT~S95/13286 An important property of the lignin-based friction material composition of this invention is its water solubility. It has been observed that the water solubility of a friction material composition comprising a lignosulfonate shows a tenfold increase in water solubility as compared to a friction material composition comprising the same level of substitution with organosolv lignin. This observation can be explained by the fact that the lignosulfonate-based friction material composition has not been incorporated into the phenolic matrix to the same extent as the lignin of this invention.
Brake pads are manufactured by blending the friction material composition and then pressing the blend at from about 375~F to about 500~F for from about 10 minutes to about 45 minutes and at a pressure of from about 350 psig to about 750 psig. Manufacturing techniques are well known in the art.
In order to evaluate the friction material composition, a series of tests were performed on friction elements such as brake pads comprising the lignin of the invention. The pads were all formed by techniques well known in the art.
Figures 1 and 2 show that replacing 20~ of the phenolic resin with organosolv lignin did not affect the stability of the coefficient of friction as the temperature was changed. A stable coefficient of friction is a requirement of friction element products since drivers require the same braking power or feel regardless of the temperature of the friction elements.
The friction material composition of this invention when formulated in brake pads result in an improvement in wear characteristics (Table 1) CA 02242~4 1998-04-17 Table 1 Inner Outer Average (mm/qm of brake ~ad) Control 0.102 0.142 0.122 10~ Lignin 0.071 0.122 0.096 20~ Lignin 0.090 0.139 0.114 A reduction of oryanic deposits on the rotor can also be observed resulting in an improvement in vibration characteristics as confirmed by noise data as shown in Figure 4 (20~ lignin) as compared to Figure 3 (control).
The use of the lignin in brake pad formulations were tested at about 300 rpm, 50 psig and 300~F according to a modified Ford Test. Figure 4 demonstrates a shift of the peak of the frequency to the (hllm~n) non-audible part of the spectrum (approximately above 16 KHz).
The invention and many of its attendant advantages will be understood from the foregoing description, and it will be apparent that various modifications and changes can be made without departing from the spirit and scope of the invention or sacrificing all of its material advantages, the compositions and processes hereinbe~ore described being merely preferred embodiments.
Claims (8)
1. A friction material composition comprising an essentially sulfur-free lignin with low water solubility, said lignin replacing from about 1 to about 30% on a weight basis with the phenolic resin in said friction material composition.
2. The composition of claim 1 wherein said lignin is an organosolv lignin.
3. A friction material composition comprising on a weight basis from about 20% to about 35% iron powder, from about 0.1% to about 1.5% hexamethylene tetramine, from about 10% to about 15% steel fiber or asbestos, from about 8% to about 14% phenolic resin, from about 7% to about 11% graphite and of from about 0.08% to about 4.2%
of an essentially sulfur-free lignin with low water solubility on a weight basis with said composition.
of an essentially sulfur-free lignin with low water solubility on a weight basis with said composition.
4. The composition of claim 3 wherein said lignin is an organosolv lignin.
5. A method for reducing noise within the range of human hearing, said noise resulting from friction element performance, said method comprising the step of incorporating in a friction element formulation a friction material composition comprising an essentially sulfur-free lignin with low water solubility, said lignin replacing from about 1 to about 30% on a weight basis with the phenolic resin in said friction material composition.
6. The method of claim 5 wherein said lignin is an organosolv lignin.
7. A method for reducing noise within the range of human hearing, said noise resulting from friction element performance, said method comprising the step of incorporating in a friction element formulation a friction material composition comprising on a weight basis from about 20% to about 35% iron powder, from about 0.1% to about 1.5% hexamethylene tetramine, from about 10% to about 15% steel fiber or asbestos, from about 8% to about 14% phenolic resin, from about 7% to about 11% graphite and of from about 0.08% to about 4.2% of an essentially sulfur-free lignin with low water solubility on a weight basis with said composition.
8. The method of claim 7 wherein said lignin is an organosolv lignin.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95939523A EP0856030A4 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
| JP9515769A JPH11513726A (en) | 1995-10-18 | 1995-10-18 | Lignin based friction material |
| PCT/US1995/013286 WO1997014747A1 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
| CA002242554A CA2242554A1 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
| BR9510654-5A BR9510654A (en) | 1995-10-18 | 1995-10-18 | Composition of friction material and noise reduction process within the range of human hearing. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1995/013286 WO1997014747A1 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
| CA002242554A CA2242554A1 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2242554A1 true CA2242554A1 (en) | 1997-04-24 |
Family
ID=25680355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002242554A Abandoned CA2242554A1 (en) | 1995-10-18 | 1995-10-18 | Lignin-based friction material |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0856030A4 (en) |
| JP (1) | JPH11513726A (en) |
| CA (1) | CA2242554A1 (en) |
| WO (1) | WO1997014747A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109851733A (en) * | 2018-12-29 | 2019-06-07 | 江南大学 | Lignin-base phenolic resin and its preparation and application |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003184921A (en) * | 2001-12-12 | 2003-07-03 | Aisin Chem Co Ltd | Dry clutch facing and manufacturing method therefor |
| EP3719145A1 (en) | 2010-01-19 | 2020-10-07 | Renmatix, Inc. | Production of fermentable sugars and lignin from biomass using supercritical fluids |
| JP5967730B2 (en) * | 2011-05-04 | 2016-08-10 | レンマティックス, インコーポレイテッドRenmatix, Inc. | Production of lignin from lignocellulosic biomass |
| US8759498B2 (en) | 2011-12-30 | 2014-06-24 | Renmatix, Inc. | Compositions comprising lignin |
| JP5898525B2 (en) * | 2012-02-27 | 2016-04-06 | 曙ブレーキ工業株式会社 | Method for producing resin composition for friction material |
| JP5918585B2 (en) * | 2012-03-23 | 2016-05-18 | 曙ブレーキ工業株式会社 | Friction material manufacturing method |
| US9534650B2 (en) | 2012-03-23 | 2017-01-03 | Akebono Brake Industry Co., Ltd. | Friction material |
| NZ629052A (en) | 2013-03-15 | 2017-04-28 | Renmatix Inc | High purity lignin, lignin compositions, and higher structured lignin |
| EP2918640A1 (en) | 2014-03-13 | 2015-09-16 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Bitumen composition |
| EP2918627A1 (en) | 2014-03-13 | 2015-09-16 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Lignin compound |
| EP4357434A3 (en) | 2014-09-26 | 2024-11-20 | Renmatix, Inc. | Adhesive compositions comprising type-ii cellulose |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6022011B2 (en) * | 1975-04-21 | 1985-05-30 | ザ・ベンデイクス・コ−ポレ−ション | organic friction material |
| US4239666A (en) * | 1979-03-02 | 1980-12-16 | The Bendix Corporation | Lignin modified friction material |
| JPS57111373A (en) * | 1980-12-27 | 1982-07-10 | Sumitomo Electric Ind Ltd | Friction material for brake |
| US4764596A (en) * | 1985-11-05 | 1988-08-16 | Repap Technologies Inc. | Recovery of lignin |
| US4920159A (en) * | 1987-12-28 | 1990-04-24 | Allies-Signal Inc. | Friction resistant composition |
| US5010156A (en) * | 1988-05-23 | 1991-04-23 | Eastman Kodak Company | Organosolv lignin-modified phenolic resins and method for their preparation |
| US5196460A (en) * | 1990-05-29 | 1993-03-23 | Repap Technologies Inc. | Rubber compositions containing high purity lignin derivatives |
| ES2040679T3 (en) * | 1991-11-07 | 1996-06-01 | Bakelite Ag | BINDER BASED ON LIGNINE AND ARTIFICIAL RESINS. |
| JPH0617030A (en) * | 1992-06-30 | 1994-01-25 | Tokico Ltd | Brake friction material |
-
1995
- 1995-10-18 CA CA002242554A patent/CA2242554A1/en not_active Abandoned
- 1995-10-18 EP EP95939523A patent/EP0856030A4/en not_active Withdrawn
- 1995-10-18 JP JP9515769A patent/JPH11513726A/en active Pending
- 1995-10-18 WO PCT/US1995/013286 patent/WO1997014747A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109851733A (en) * | 2018-12-29 | 2019-06-07 | 江南大学 | Lignin-base phenolic resin and its preparation and application |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0856030A4 (en) | 1999-11-17 |
| WO1997014747A1 (en) | 1997-04-24 |
| JPH11513726A (en) | 1999-11-24 |
| EP0856030A1 (en) | 1998-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |