WO1998050467A1 - Composition de resine et panneau realise avec cette resine - Google Patents

Composition de resine et panneau realise avec cette resine Download PDF

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Publication number
WO1998050467A1
WO1998050467A1 PCT/JP1998/001426 JP9801426W WO9850467A1 WO 1998050467 A1 WO1998050467 A1 WO 1998050467A1 JP 9801426 W JP9801426 W JP 9801426W WO 9850467 A1 WO9850467 A1 WO 9850467A1
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WO
WIPO (PCT)
Prior art keywords
resin composition
lignin
weight
board
phenol
Prior art date
Application number
PCT/JP1998/001426
Other languages
English (en)
Japanese (ja)
Inventor
Tsuyoshi Kono
Original Assignee
Tsuyoshi Kono
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 Tsuyoshi Kono filed Critical Tsuyoshi Kono
Priority to JP54790998A priority Critical patent/JP3361819B2/ja
Publication of WO1998050467A1 publication Critical patent/WO1998050467A1/fr

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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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C08L61/14—Modified phenol-aldehyde condensates

Definitions

  • the present invention relates to a resin composition using lignin used as an adhesive, a binder, a molding material, and the like, and a board using the same as an adhesive, such as a particle board and a fiber board.
  • phenol aldehyde resins exhibit excellent water resistance, they are widely used in adhesives for wood and the like, particularly in fields requiring water resistance.
  • An object of the present invention is to provide a resin composition which exhibits excellent strength performance and water resistance by using lignin, has a high use ratio of lignin, and is economically advantageous as compared with a commercially available phenol aldehyde resin. It is in.
  • Another object of the present invention is to provide a board having excellent strength performance and water resistance using such a resin composition.
  • lignin of the Gramineae plant is extremely advantageous as a raw material for a resin composition.
  • Lignin is industrially produced by extraction from pulp waste liquor, but until now pulp production in Japan and Western Europe has been essentially only wood pulp. As a result, research on the use of lignin was limited to wood lignin.
  • the present inventors have obtained a resin composition having excellent strength performance and water resistance by effectively using lignin of the grass family. That is, the resin composition of the present invention is a resin composition in which phenols and aldehydes are reacted with lignin, and that 30% or more of non-volatile components are components derived from a lignin plant of the Poaceae family. It is a feature.
  • the board of the present invention may be formed by adding a resin composition containing the above resin composition or a component derived from lignin derived from a grass plant of 30% by weight or more to a lignocellulose substance, and heating and pressurizing the board.
  • a resin composition containing the above resin composition or a component derived from lignin derived from a grass plant of 30% by weight or more to a lignocellulose substance, and heating and pressurizing the board.
  • a particle board, a fiber board, and the like are included.
  • Gramineous plant lignin to be used in the resin composition of the present invention includes lignin of all grasses such as rice, wheat, bamboo, sugar cane, ash and kolyan.
  • Such lignin of the Gramineae plant may be of course directly extracted from the Gramineae plant, but the one extracted from the pulp waste liquid is industrially advantageous.
  • the types of digestion methods include so-called chemical pulping, semi-chemical pulping, thermomechanical pulping, and organic methods such as the Kraft method, the sulfite method, and the soda method. There are solvent methods and the like, and any of them can be used.
  • the lignin used in the resin composition of the present invention is preferably composed of only the above-mentioned lignin of the grass family, but if it is 50% by weight or less, lignin other than the grass family such as wood may be used. Good.
  • phenols used in the resin composition of the present invention all phenols such as phenol, cresol, xylenol, bisphenol A, bisphenol F, resorcinol, etc. can be used. It is particularly preferable to use phenol from the viewpoint.
  • the use amount thereof is preferably 100% by weight or less, and particularly preferably 5 to 60% by weight, based on the lignin of the grass family. The amount used may exceed 100% by weight, but it will only increase the cost and cannot improve the physical properties.
  • aldehydes formaldehyde, acetate aldehyde, furfural, benzaldehyde, dalioxal, etc. can be used, but in terms of performance and cost. It is particularly preferred to use formaldehyde or furfural. These may be used alone or in combination of two or more. The amount used is preferably in the range of 0.2 to 5 in terms of the molar ratio of formyl group to phenol monomer.
  • the use ratio is preferably at least 30% by weight, more preferably at least 50% by weight of the whole aldehyde.
  • the use ratio is preferably at least 10% by weight, more preferably at least 30% by weight of the whole aldehyde.
  • formaldehyde all formaldehydes such as formalin, paraformaldehyde and polyxylene can be used.
  • the amount used is preferably in the range of 1.2 to 5.0, more preferably in the range of 1.8 to 3.5, as a molar ratio to the phenol monomer.
  • formaldehyde By using a small amount of formaldehyde, the resin composition exhibits excellent strength performance.
  • the amount of the furfural is preferably in the range of 0.2 to 3.0, more preferably in the range of 0.5 to 2.0 in terms of molar ratio to the phenol monomer.
  • Use of furfural is effective in improving water resistance.
  • the use ratio of formaldehyde to furfural is preferably in the range of 0.1 to 20 in molar ratio.
  • furfuryl alcohol which is a derivative of furfural, may be used instead of furfural.
  • the resin composition of the present invention is characterized in that the use of the above-mentioned lignin, phenols and aldehydes allows the non-volatile matter to contain at least 30% by weight or more of a component derived from a waste liquid of a grass pulp, preferably 50 to 95% by weight or more. Particularly preferably, the content is 60 to 80% by weight. Those containing less than 30% by weight of components derived from lignin of the Gramineae plant cannot achieve the object of the present invention. In addition, this content indicates the weight% of the lignin of the Gramineae plant used in the production of the resin composition, based on the nonvolatile content of the resin composition.
  • the reaction between the lignin and the phenols and aldehydes is preferably carried out under an alkaline condition of pH 9 or more, and pH HI 0 or more. More preferably, the reaction is carried out under alkaline conditions.
  • the catalyst any alkali catalyst that satisfies such pH conditions, such as oxides and hydroxides of alkali metals and alkaline earth metals, can be used.
  • novolak resin composition by reacting lignin, phenol and formaldehyde in the presence of an acidic catalyst such as oxalic acid, hydrochloric acid or sulfuric acid.
  • the reaction of lignin with phenols and aldehydes includes a method of reacting aldehydes with a reaction product of lignin and phenols, a method of simultaneously reacting lignin with phenols and aldehydes, and a method of reacting phenols with aldehydes.
  • a method of reacting lignin with a reaction product a method of reacting lignin with a reaction product of a phenol and an aldehyde is particularly preferable.
  • the weight average molecular weight is 120 to 500, preferably 150 to 300, and the content of the methylol compound of the phenol monomer is 2
  • the reaction product of phenols and formaldehyde in an amount of 0% by weight or more, preferably 40% by weight or more is used.
  • the methylol form of the phenol monomer includes monomethylol, dimethylol, and trimethylol, and the higher the content of trimethylol and then dimethylol, the more preferable.
  • reaction products of the above-mentioned phenols and formaldehyde are, for example, a molar ratio of formaldehyde to phenol monomer of 1.8 to 3.5 and a molar ratio of alkali metal to phenol monomer of 0.1 to 0.5; It is obtained by reacting at a temperature of 880 ° C. for 30 minutes to 2 hours.
  • a desired resin composition is obtained by adding the reaction product of the above phenols and aldehydes to lignin and reacting at a temperature of 50 to 95 ° C for 20 minutes to 5 hours.
  • Another example of a method of reacting lignin with a reaction product of the above-mentioned phenols and aldehydes is one using furfural as the aldehyde.
  • furfural as the aldehyde.
  • reaction products of the above phenols and aldehydes are as follows: the molar ratio of furfural to phenol monomer is 0.5 to 2.0, and the molar ratio of alkali metal to phenol monomer is 0.1 to 1.0. It is obtained by reacting at a temperature of 50 to 130 ° C. for 20 minutes to 5 hours.
  • a desired resin composition is obtained by adding the reaction product of the above phenols and aldehydes to lignin and reacting at a temperature of 60 to 95 ° C for 1 to 8 hours.
  • the resin composition of the present invention is generally used in the form of a liquid, particularly an aqueous solution or a suspension of water, but may be used in the form of a powder by dehydration to dryness.
  • thermosetting preferably 150 ° C. or more, more preferably 180 ° C. to 250 ° C. It cures when heated at a temperature of C.
  • a resin composition adheresive
  • a resin composition can be cured at room temperature by adding 0.5 to 5.0 moles of alkali metal to phenol mononuclear and mixing with an organic acid ester when used. It is.
  • the resin composition of the present invention can be used in all applications where conventional thermosetting resins are used, such as adhesives, binders, molding materials, etc., but adhesives, especially particle boards, fiber boards, and plywood Demonstrates excellent performance as an adhesive for wood, etc. Further, the resin composition of the present invention may be used in combination with other agents such as a water repellent, a release agent, and a flame retardant. Further, the resin composition of the present invention may be used in combination with another synthetic resin such as a urea resin and a melamine resin.
  • the board in the present invention is a board formed by mixing small pieces of a lignocellulosic substance such as wood, pulp, or vegetation, such as particle board and fiber board, with an adhesive, and applying heat and pressure. is there.
  • the board of the present invention preferably contains 30% by weight or more of a component derived from a lignin of a grass family.
  • the resin composition containing 50 to 95% by weight or more, particularly preferably 60 to 80% by weight is 0.2 to 30% by weight on a dry weight basis with respect to the lignocellulose substance. Or ⁇ to 20% by weight, mixed and heated and pressed to form a plate.
  • the adhesive the above-described resin composition of the present invention is preferable, but lignin itself may be used. Some wood adhesives may be used in combination.
  • the hot press forming of the board of the present invention may be carried out by using an ordinary hot press, but is not limited thereto.
  • an ordinary hot press but is not limited thereto.
  • a steam injection press, a high frequency press, or the like may be used.
  • the molding temperature is preferably from 180 to 250 ° C, more preferably from 200 to 240 ° C. If the molding temperature exceeds 250 ° C, the lignocellulosic material deteriorates, which is not preferable.
  • the molding time depends mainly on the target board thickness, molding temperature and the type of hot press used.
  • the molding pressure mainly depends on the specific gravity and thickness of the target board and the type of hot press used.
  • the board of the present invention has mechanical strength and water resistance equal to or higher than that of a board product using a conventional phenol aldehyde resin adhesive.
  • additives such as a water repellent, a release agent, and a preservative may be used. These additives may be added to and mixed with the resin composition (adhesive) in advance. It may be added separately from the resin composition (adhesive) during board production.
  • the reason why the resin composition of the present invention exhibits excellent performance is considered to be due to the special structure of lignin of the grass family.
  • Lignin other than gramineous plants such as wood has a methoxy group in the luteol position of the phenol skeleton as shown in the formula (1) or (2), while lignin of the gramineous plant is represented by the formula (3). As shown, there is no methoxy group.
  • phenol is said to have a reactive activity at the ortho or para position, and lignin with a phenol skeleton having no methoxy group at the ortho position is rich in reactivity It is expected to be.
  • the reason why phenol is preferably used in the form of a methylol in the reaction between lignin and phenol is exemplified by using trimethylol phenol, which is the most preferred of the methylols.
  • Trimethylolphenol represented by the formula (4) is easily dehydrated and condensed with lignin to form an oligomer in which the phenol monomer represented by the formula (5) and lignin are alternately polymerized with a methylene group interposed therebetween.
  • the methylol groups required for the crosslinking reaction remain in the phenol skeleton.
  • a resin composition of a type that is cured by a cross-linking reaction of a methylol group by efficiently using a small amount of phenol and formaldehyde is formed.
  • R represents lignin.
  • lignin powder extracted from barley straw pulp waste liquid by the soda cooking method was used as the lignin of the grass family.
  • lignin powder extracted from conifer pulp waste liquid by the craft digestion method was used as wood lignin.
  • the measured value of the weight-average molecular weight in this example was obtained by gel filtration chromatography (manufactured by Shimadzu Corporation) for the THF (tetrahydrofuran) soluble matter after neutralizing the sample to pH 5-7 with formic acid. Using a column "Shimazu LC Column GP C-801 150" "), carrier: THF 1 cc / min, detector UV. The phenol monomer methylol content was It is represented by the area% of the molecular weight distribution chart.
  • the particle board is made of flakes with a water content of 5% obtained by cutting the building demolition material using a knife ring flaker (pal I man) with a blade of 0.6 mm. Apply 10% by weight of adhesive with a spray gun After addition, the plated hands and pine Bok Fomin grayed the forming box of 22 cm square, with a spacer size of 1 cm (target specific gravity 0. 7 g, cm3), at a pressure 50 kgf / cm 2 2 Manufactured by heating at a temperature of 10 ° C. for 15 minutes. The flexural strength was measured to examine the strength performance of the board, and the water absorption thickness expansion rate was measured to examine the water resistance.
  • the flexural strength was determined by the average value of the measured values of three test pieces pressed to a size of 50 ⁇ 200 mm according to JISA 59085.5.
  • the coefficient of expansion of the water absorption thickness was determined by the average value of the measured values of three test pieces pressed to a size of 50 ⁇ 50 mm according to JISA 5908 5.10.
  • reaction product X of phenol and formaldehyde was obtained.
  • the content of the methylol form of the phenol monomer in the reaction product X is 0-methylolphenol 9%, p-methylolphenol and 2,6-dimethylol 10%, 2,4-dimethylolphenol 12%, Trimethylolphenol was 30%, for a total of 61%.
  • the weight average molecular weight was 158.
  • the above reaction product X is added to the gramineous plant dandanin such that the ratio of the phenol in the reaction product becomes 20% by weight relative to the gramineous plant lignin, and further the concentration becomes 40% by weight.
  • the ratio of the component derived from lignin of the grass family was 74% by weight.
  • a resin composition was produced in the same manner as in Example 1 except that wood lignin was used instead of grass lignin.
  • the above reaction product Y is added to the gramineous plant dandanin such that the ratio of the phenol in the reaction product Y becomes 20% by weight with respect to the gramineous plant lignin, and further, the ag becomes 40% by weight.
  • water was added and reacted at 80 ° C. for 3 hours to produce a resin composition of the present invention.
  • the proportion of the component derived from the lignin of the grass family was 60% by weight.
  • a particle board was manufactured using this resin composition as an adhesive.
  • the bending strength of this board was 15.6 N / cm 2 , and the coefficient of expansion of the water absorption thickness was 11%.
  • a resin composition was produced in the same manner as in Example 1 except that wood lignin was used instead of grass lignin.
  • the reaction product X produced in Example 1 was added to the grass lignin such that the ratio of phenol in the reaction product X was 10% by weight with respect to the grass lignin.
  • the reaction product Y prepared in the above is added so that the ratio of the phenol in the reaction product Y becomes 10% by weight with respect to the lignin of the grass family, and water is further added so that the concentration becomes 40% by weight.
  • the mixture was added and reacted at 8 (TC for 2 hours) to produce a resin composition of the present invention.
  • the ratio of a component derived from a lignin derived from a gramineous plant was 67% by weight.
  • a particle board was manufactured using this resin composition as an adhesive.
  • the bending strength of this board was 23.1 N / cm 2 , and the coefficient of expansion of the water absorption thickness was 6%.
  • the resin composition of the present invention exhibits excellent strength performance equal to or higher than that of a conventional phenol aldehyde resin.
  • the resin composition of the present invention exhibits excellent water resistance equal to or higher than that of a conventional phenol aldehyde resin.
  • the resin composition of the present invention is economically advantageous because it has a high ratio of lignin and can be produced at a lower raw material cost than conventional phenolaldehyde resins.
  • the resin composition of the present invention exhibits particularly excellent strength performance as an adhesive for lignocellulosic substances such as particle board, fiber board, and plywood.
  • the resin composition of the present invention exhibits particularly excellent water resistance as an adhesive for lignocellulosic substances such as particle board, fiber board, and plywood.
  • the board of the present invention has excellent mechanical strength.
  • the board of the present invention has excellent water resistance.
  • the resin composition of the present invention solves the problem of environmental pollution due to pulp waste liquid.
  • the board of the present invention is economically advantageous because a lignocellulosic board can be produced at a low raw material cost.
  • the board of the present invention is safe for the human body since the amount of formaldehyde used is extremely small or not used at all as compared with the conventional wood bonding. is there.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Composition de résine présentant une excellente résistance à la contrainte et une excellente résistance à l'eau grâce à l'utilisation d'une lignine, et panneau formé de cette composition de résine et présentant par conséquent ces mêmes qualités de résistance à la contrainte et à l'eau. La composition de résine est obtenue par mise en réaction d'une lignine avec un phénol et un aldéhyde, au moins 30 % en poids de la matière non volatile étant formés d'ingrédients dérivés d'une lignine de graminée. La composition de résine est ajoutée à une substance de lignocellulose à raison de 0,2 à 30 % en poids de la matière lignocellulosique mesurée à sec, et ce mélange est chauffé et comprimé pour produire un panneau.
PCT/JP1998/001426 1997-05-05 1998-03-30 Composition de resine et panneau realise avec cette resine WO1998050467A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP54790998A JP3361819B2 (ja) 1997-05-05 1998-03-30 接着剤及びそれを使用したボード

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP15147197 1997-05-05
JP9/151471 1997-05-05

Publications (1)

Publication Number Publication Date
WO1998050467A1 true WO1998050467A1 (fr) 1998-11-12

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Application Number Title Priority Date Filing Date
PCT/JP1998/001426 WO1998050467A1 (fr) 1997-05-05 1998-03-30 Composition de resine et panneau realise avec cette resine

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JP (1) JP3361819B2 (fr)
WO (1) WO1998050467A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN1305967C (zh) * 2003-05-06 2007-03-21 藤炭素株式会社 生物质树脂组合物、其制法和该生物质树脂组合物成型材料
JP2008156601A (ja) * 2006-12-01 2008-07-10 Toyota Auto Body Co Ltd リグニン変性ノボラック型フェノール系樹脂、その製造方法及びフェノール系樹脂成形材料
JP2011099083A (ja) * 2009-11-09 2011-05-19 Kono Shinsozai Kaihatsu Kk エポキシ樹脂
EP3279268A3 (fr) * 2016-08-04 2018-03-07 Akebono Brake Industry Co., Ltd. Composition de résine thermodurcissable, matériau de friction et procédé de production de composition de résine thermodurcissable
JP2019518087A (ja) * 2016-04-01 2019-06-27 コンパニー ゼネラール デ エタブリッスマン ミシュラン 熱硬化性樹脂及びラテックスを含む水性接着剤組成物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3049611A1 (fr) 2016-04-01 2017-10-06 Michelin & Cie Composition adhesive aqueuse comportant une resine thermodurcissable

Citations (2)

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Publication number Priority date Publication date Assignee Title
JPS55112226A (en) * 1979-02-20 1980-08-29 Akira Shinjo Production of shell-moldable lignin-phenol resin composition
JPH01158022A (ja) * 1987-09-04 1989-06-21 Oji Paper Co Ltd リグニン−フェノール樹脂組成物

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JPS51148731A (en) * 1975-06-17 1976-12-21 Eidai Co Ltd A process for preparing lignin-phenol co-condensation resin adhesive
CA1138589A (fr) * 1979-04-20 1982-12-28 Krishan K. Sudan Liant de resine phenolique au lignosulfonate
JP2595307B2 (ja) * 1987-09-04 1997-04-02 王子製紙株式会社 リグノセルロース−フェノール樹脂組成物
JPH0741681A (ja) * 1993-07-28 1995-02-10 Kyoto Mokuzai Shigen Kaihatsu Kyodo Kumiai リグノセルロース系物質の部分樹脂化組成物
JPH07196923A (ja) * 1993-12-28 1995-08-01 Kyoto Mokuzai Shigen Kaihatsu Kyodo Kumiai リグノセルロース系物質の部分樹脂化組成物及びその製造法
US5728269A (en) * 1994-12-22 1998-03-17 Atsushi Onishi Board produced from malvaceous bast plant and process for producing the same
WO1997017412A1 (fr) * 1995-11-06 1997-05-15 Tsuyoshi Kono Adhesif et panneaux fabriques a l'aide de cet adhesif
JPH10305409A (ja) * 1997-04-30 1998-11-17 Takeshi Kono イネ科植物リグニンを使用したボードとその製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55112226A (en) * 1979-02-20 1980-08-29 Akira Shinjo Production of shell-moldable lignin-phenol resin composition
JPH01158022A (ja) * 1987-09-04 1989-06-21 Oji Paper Co Ltd リグニン−フェノール樹脂組成物

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1305967C (zh) * 2003-05-06 2007-03-21 藤炭素株式会社 生物质树脂组合物、其制法和该生物质树脂组合物成型材料
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
JP2008156601A (ja) * 2006-12-01 2008-07-10 Toyota Auto Body Co Ltd リグニン変性ノボラック型フェノール系樹脂、その製造方法及びフェノール系樹脂成形材料
JP2011099083A (ja) * 2009-11-09 2011-05-19 Kono Shinsozai Kaihatsu Kk エポキシ樹脂
JP2019518087A (ja) * 2016-04-01 2019-06-27 コンパニー ゼネラール デ エタブリッスマン ミシュラン 熱硬化性樹脂及びラテックスを含む水性接着剤組成物
EP3279268A3 (fr) * 2016-08-04 2018-03-07 Akebono Brake Industry Co., Ltd. Composition de résine thermodurcissable, matériau de friction et procédé de production de composition de résine thermodurcissable
US10598240B2 (en) 2016-08-04 2020-03-24 Akebono Brake Industry Co., Ltd. Thermosetting resin composition, friction material and method for producing thermosetting resin composition

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