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WO2016027537A1 - Composition de résine et objet moulé - Google Patents

Composition de résine et objet moulé Download PDF

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Publication number
WO2016027537A1
WO2016027537A1 PCT/JP2015/064808 JP2015064808W WO2016027537A1 WO 2016027537 A1 WO2016027537 A1 WO 2016027537A1 JP 2015064808 W JP2015064808 W JP 2015064808W WO 2016027537 A1 WO2016027537 A1 WO 2016027537A1
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WIPO (PCT)
Prior art keywords
lignin
resin composition
composition according
resin
mass
Prior art date
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Ceased
Application number
PCT/JP2015/064808
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English (en)
Japanese (ja)
Inventor
津田　義博
優希 中村
小山　直之
郁子 荘司
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Resonac Corp
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Hitachi Chemical Co Ltd
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Filing date
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Publication of WO2016027537A1 publication Critical patent/WO2016027537A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • 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

Definitions

  • the present invention relates to a resin composition and a molded body using the same, and more specifically to a resin composition containing lignin as an essential component and a molded body using the same.
  • Lignin is attracting attention as a raw material for heat-resistant resin materials derived from plants.
  • Lignin is a polymer having a crosslinked structure having a basic skeleton of hydroxyphenylpropane units.
  • the tree forms an interpenetrating network (IPN; Interpenetrating Polymer Polymer Network) structure of a hydrophilic linear polymer polysaccharide (cellulose and hemicellulose) and a hydrophobic cross-linked lignin.
  • IPN Interpenetrating Polymer Polymer Network
  • Lignin accounts for about 25% by weight of trees and has an irregular and extremely complex polyphenolic chemical structure.
  • Such lignin is characterized by having extremely excellent heat resistance compared to other bioplastics represented by polylactic acid, and has been sufficient in heat resistance so far, such as automobile parts and OA related parts. It is expected to be applied to applications that could not be applied due to lack of it.
  • lignin Unlike general phenolic resins, lignin has many alcoholic hydroxyl groups in addition to phenolic hydroxyl groups, so when used as a substitute for phenolic resins, it has excellent adhesion to metals, etc. is expected.
  • lignin since lignin has a rigid pyranose ring, furanose ring and aromatic ring in the molecule, it becomes a very hard composition when trying to cure lignin alone. Therefore, workability at the time of kneading is deteriorated, and there is a problem that the molded product becomes hard and brittle and impact resistance is lowered.
  • Patent Document 1 discloses a method of using a common petroleum-derived phenolic resin in Examples, but when the molecular weight of lignin is large, more specifically, when the molecular weight is larger than 2000, the softening point is There was a problem that it became too high to be molded (see Patent Document 1, paragraph 0016). Then, an object of this invention is to provide the resin composition of the high plant origin using the woody material derived from a plant from a viewpoint of environmental load reduction. Specifically, a resin composition having a plant-derived lignin as a main raw material, having a high degree of plant origin, good workability, and excellent heat resistance, bending strength, tensile strength, and adhesion to metal, and The object is to provide a molded body.
  • the present invention (1) A resin composition comprising lignin, a phenol novolac resin, a fibrous filler and a curing agent, wherein the mass ratio of the lignin to the phenol novolac resin is 20:80 to 52:48, (2) The resin composition according to the above (1), wherein the lignin has a weight average molecular weight of 100 to 7000, (3) The resin composition according to the above (1) or (2), wherein the sulfur atom content in the lignin is 2% by mass or less, (4) The resin composition according to any one of the above (1) to (3), wherein the fibers constituting the fibrous filler are inorganic fibers, (5) The resin composition according to (4), wherein the inorganic fiber is a glass fiber, (6) The resin composition according to (5), wherein the glass fiber has a length of 1 to 20 mm, (7) The resin composition according to any one of (1) to (6), wherein the curing agent is an aldehyde compound or a compound that forms formaldehy
  • the present invention it is possible to provide a resin composition and a molded article having a high degree of plant origin, good workability, excellent heat resistance, bending strength, tensile strength, and adhesion to metal, As a result, the effect of reducing the amount of fossil resources used and the amount of carbon dioxide emission can be obtained, and a resin material suitable for protecting the global environment can be provided.
  • the resin composition of the present invention is characterized by containing lignin, a phenol novolac resin, a fibrous filler and a curing agent. Details will be described below.
  • the present invention is characterized in that lignin is used as a main raw material and the complex chemical structure of lignin is utilized. More specifically, a phenolic hydroxyl group and an alcoholic hydroxyl group possessed by lignin are used to form a three-dimensional crosslinked structure using a curing agent. Thereby, it is possible to obtain a resin material and a molded body having a high glass transition temperature.
  • ligninsulfonate examples include lignin sulfonate, alkali lignin, organosolv lignin, solvolysis lignin, filamentous fungus treated lignin, dioxane lignin, milled wood lignin, and explosive lignin that are by-produced by the sulfuric acid method.
  • the lignin used in the present invention is preferably one obtained by removing cellulose and hemicellulose components from a plant by a method using water.
  • a method of separating from cellulose and hemicellulose components a method using a method of separating by treatment with high-temperature water or steam, pressure (for example, a steaming method, a craft method, an explosion method, etc.) is used. preferable.
  • the lignin used in the present invention preferably has a weight average molecular weight of 100 to 7000 in terms of polystyrene based on GPC (gel permeation chromatography) method.
  • GPC gel permeation chromatography
  • the weight average molecular weight of lignin is 7000 or less, solubility in an organic solvent is ensured, and when it is 100 or more, the effects of the present invention utilizing the above-described lignin structure, that is, effects such as high heat resistance are exhibited.
  • a resin composition can be obtained.
  • the weight average molecular weight of lignin is more preferably 200 to 5,000, and further preferably 500 to 4,000.
  • the conditions for GPC measurement are the same as those described in the examples.
  • the content of lignin in the resin composition of the present invention is preferably 3 to 60% by mass as the amount of lignin soluble in an organic solvent.
  • the amount of lignin is 3% by mass or more, the effect of the present invention, that is, the effect of reducing fossil resources and carbon dioxide can be obtained.
  • the content of lignin soluble in an organic solvent in the resin composition is more preferably 5 to 40% by mass, further preferably 8 to 30% by mass, and particularly preferably 10 to 20% by mass. It is a range.
  • biomass is used as a method for separating and extracting lignin from a tree.
  • a method for separating and extracting lignin from a tree a method is generally used in which biomass is decomposed by treatment in the presence of a solvent, in the presence of a catalyst, and / or under conditions of high temperature and high pressure.
  • the biomass is adjusted to a certain size, placed in a pressure vessel equipped with a stirrer and a heating device together with a solvent and optionally a catalyst, and stirred while heating and pressurizing to decompose the biomass.
  • a pressure vessel equipped with a stirrer and a heating device together with a solvent and optionally a catalyst, and stirred while heating and pressurizing to decompose the biomass.
  • the content of the pressure vessel is filtered to remove the filtrate, and the water-insoluble matter is washed with water and separated.
  • lignin can be obtained by immersing the water-insoluble matter in a solvent in which the lignin compound is soluble, extracting the lignin compound, and distilling off the solvent.
  • the size of biomass is preferably about 100 ⁇ m to 1 cm, more preferably 200 ⁇ m to 500 ⁇ m.
  • the shape of the biomass is not particularly limited, and may be any of a block shape, a chip shape, a powder shape, and the like
  • Specific methods for separating and extracting lignin from trees include the kraft method, sulfuric acid method, and explosion method. Many of the lignins currently produced in large quantities are obtained as residues during the production of cellulose, which is a raw material such as paper and bioethanol.
  • the kraft method is a method in which a mixed solution of sodium hydroxide and sodium sulfide is steamed at 160 to 170 ° C. for 5 to 12 hours to elute lignin in wood as alkaline thiolignin into waste liquid.
  • the sulfuric acid method wood chips are steamed with a mixed solution of acidic sulfite and sulfurous acid at 130 to 145 ° C., 6 to 8 kg / cm 2 for 10 to 12 hours, and lignin in the wood is converted into lignin sulfonate in the waste liquid.
  • This is an elution method.
  • An example of the explosion method is a steam explosion method. The steam explosion method crushes plants in a short time by hydrolysis with high-temperature and high-pressure steam and a physical crushing effect by instantaneously releasing the pressure. In this method, lignin containing no sulfur atom in the lignin or lignin having a low content of sulfur atoms can be obtained.
  • An organic solvent is preferably used for the extraction, and examples thereof include an alcohol solvent and a hydrous alcohol solvent obtained by mixing alcohol and water.
  • examples of other organic solvents include phenols such as phenol and cresol, ketones such as acetone, ethers, a mixed solvent of these organic solvents and water, and the like.
  • an alcohol solvent is preferable.
  • Examples of the alcohol solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, n-hexanol, benzyl alcohol, cyclohexanol and other monools, ethylene glycol, diethylene glycol, 1, Examples include polyols such as 4-butanediol, 1,6-hexanediol, trimethylolpropane, glycerin, triethanolamine and the like.
  • an alcohol obtained from a natural substance is preferable from the viewpoint of reducing the environmental load.
  • examples include glycol, glycerin, and hydroxymethylfurfural.
  • One of the above organic solvents may be used alone, or a mixture of two or more organic solvents may be used. It is preferable to use ion-exchanged water as water in the case of using a water-containing organic solvent obtained by mixing an organic solvent and water.
  • the water content in the water-containing organic solvent is preferably more than 0% by mass to 70% by mass. Since lignin has low solubility in water, it is difficult to extract lignin if only water is used as a solvent. Moreover, it is possible to control the weight average molecular weight of the lignin obtained by selecting the solvent to be used.
  • the resin composition of the present invention may contain components other than lignin, such as cellulose and hemicellulose, which are obtained when lignin is separated from trees and taken out as long as the effects of the present invention are not impaired.
  • the lignin in the present invention includes a lignin derivative obtained by reacting lignin with acetylation, methylation, halogenation, nitration, sulfonation or the like, or a lignin derivative obtained by reacting lignin with sodium sulfide, hydrogen sulfide, or the like. Including.
  • a phenol novolac resin is used, preferably having a low softening point, and more preferably a phenol novolac resin having a softening point of 100 ° C. or less as a crosslinking agent.
  • a resin having such a low softening point and a specific structure as a crosslinking agent while maintaining a high degree of plant origin, workability, heat resistance, bending strength, tensile strength, and metal A resin composition excellent in adhesiveness can be obtained.
  • the softening point of the phenol novolac resin is more preferably 50 to 95 ° C, and particularly preferably 70 to 90 ° C.
  • phenol novolac resins having a softening point of 100 ° C. or less include HP-850N (manufactured by Hitachi Chemical Co., Ltd., softening point 83 ° C.), TD-2131 (manufactured by DIC Corporation, softening point 78-82 ° C.) TD-2106 (manufactured by DIC Corporation, softening point 88 to 95 ° C.) and the like.
  • the softening point can be measured by the ring and ball method in a glycerin bath described in JIS K7234.
  • the phenol novolac resin is contained in the lignin so that the mass ratio of the lignin to the phenol novolac resin is 20:80 to 52:48.
  • the content of the phenol novolac resin is less than the above range, the resin composition is too hard, workability is poor, and it may be difficult to produce a molded body, and a molded body can be obtained. However, the molded body becomes hard and brittle, and the impact resistance is low.
  • the mass ratio of lignin to phenol novolac resin in the resin composition of the present invention is preferably 25:75 to 50:50, more preferably 35:65 to 45:55.
  • the fibrous filler used in the present invention includes natural fillers and chemical fillers.
  • Natural fillers include plant-based, animal-based and mineral-based fillers.
  • Plant fillers include cotton, bamboo, ramie, flax (linen), manila hemp (avaca), sisal hemp, jute, kenaf, banana, coconut, straw, sugar cane, cedar, cypress, spruce, Examples thereof include fibers such as pine, fir and larch, and pulverized powder of the fibers.
  • animal fillers include animal hair fibers, silk fibers, and pulverized powders of the fibers.
  • minerals include asbestos, basalt (basalt) fiber, and pulverized powder of the fiber.
  • Chemical fillers include inorganic fillers and organic fillers.
  • examples of the inorganic filler include carbon fiber and glass fiber.
  • examples of the organic filler include fibrous fillers such as polyester, polyamide, acrylic, urethane, aramid, and nylon. These fillers can be used alone or in combination of two or more.
  • strength of a molded object can be raised by using a fibrous filler.
  • the content of the fibrous filler in the resin composition of the present invention is preferably 2 to 400 parts by mass with respect to the total amount of lignin and phenol novolac resin of 100 parts by mass from the viewpoint of the strength of the molded product. 300 parts by mass is more preferable, and 15 to 250 parts by mass is even more preferable.
  • various mineral grounds paper powder, chitin powder, chitosan powder, powders derived from natural products such as protein and starch, carbon-based fillers such as graphite, activated carbon and graphite, iron, copper, nickel, aluminum
  • Metal fillers such as silica, alumina, titanium oxide, iron oxide, zinc oxide, magnesium oxide, tin oxide, antimony oxide, barium ferrite, strontium ferrite and other oxide fillers, aluminum hydroxide, magnesium hydroxide, etc.
  • Hydroxide filler such as calcium carbonate, calcium carbonate, silicate filler such as talc, clay, mica, calcium silicate, glass, glass hollow sphere, calcium titanate, nitriding
  • carbonate filler such as calcium carbonate, calcium carbonate
  • silicate filler such as talc, clay, mica, calcium silicate, glass, glass hollow sphere, calcium titanate, nitriding
  • examples include other inorganic fillers such as aluminum and silicon carbide.
  • aldehyde is suitable as the curing agent used in the present invention.
  • aldehydes include formaldehyde, paraformaldehyde, trioxane, acetaldehyde, propionaldehyde, chloral, furfural, glyoxazole, n-butyraldehyde, caproaldehyde, allylaldehyde, benzaldehyde, crotonaldehyde, acrolein, phenylacetaldehyde, o-tolualdehyde, Salicylaldehyde and the like can be mentioned.
  • generates formaldehyde is mentioned as a hardening
  • the compound that generates formaldehyde include hexamethylenetetramine.
  • hexamethylenetetramine is preferable from the viewpoint of curability and heat resistance.
  • curing agent can also be used individually or in combination of 2 or more types.
  • the content of the curing agent in the resin composition of the present invention is preferably 1 to 50 parts by mass, from the viewpoint of curability and heat resistance, with respect to 100 parts by mass of the total amount of lignin and phenol novolac resin. More preferred is 3 parts by mass, and still more preferred is 3 to 30 parts by mass.
  • the resin composition of the present invention may contain a curing accelerator.
  • the curing accelerator is not particularly limited and is a cycloamidine compound, a quinone compound, a tertiary amine, an organic phosphine, 1-cyanoethyl-2-phenylimidazole, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4.
  • -Imidazoles such as methylimidazole and 2-heptadecylimidazole, calcium hydroxide (slaked lime, etc.), organic acids having aromatic rings or alicyclic rings, and the like.
  • calcium hydroxide such as slaked lime
  • an organic acid having an aromatic ring or an alicyclic ring are preferred because a high-strength molded body that can be cured at a low temperature is obtained.
  • the organic acid having an aromatic ring or alicyclic ring include benzoic acid, salicylic acid, (o-, m- or p-) toluic acid, (o-, m- or p-) cresotic acid, gallic acid, 1-naphthoic acid.
  • Aromatic monocarboxylic acids such as 2-naphthoic acid, aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, and mellitic acid, cyclohexanecarboxylic acid, and 5-norbornene-2-carboxylic acid Examples thereof include alicyclic monocarboxylic acids such as acid, 1,2-cyclohexanedicarboxylic acid, and 1,4-cyclohexanedicarboxylic acid, and alicyclic polyvalent carboxylic acids.
  • the content of the curing accelerator is preferably 0.1 to 20 parts by mass, preferably 0.5 to 15 parts by mass in terms of moldability with respect to 100 parts by mass of the total amount of lignin and phenol novolac resin in the resin composition. Part is more preferable, and 1 to 10 parts by mass is further preferable.
  • the resin composition of the present invention includes silane coupling agents such as epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, vinyl silane, titanate coupling agent, aluminum coupling agent, aluminum / zirconium coupling agent, and other cups.
  • a ring agent may be included.
  • silane coupling agents are preferred. Adhesiveness with a metal etc. improves by using a coupling agent.
  • the content of the coupling agent is preferably 0.1 to 10 parts by mass and more preferably 1 to 5 parts by mass with respect to 100 parts by mass of the total amount of lignin and phenol novolac resin in the resin composition.
  • the resin composition of the present invention may contain a release agent. This is because release from the mold can be easily performed when the resin composition of the present invention is molded.
  • Release agents include polyethylene waxes, higher fatty acid esters, fatty acid amides, ketone-amines, synthetic waxes such as hydrogenated oil, natural waxes such as paraffin wax and montan wax, higher fatty acids such as stearic acid and zinc stearate, and the like. The metal salt etc. are mentioned.
  • the resin composition of the present invention can contain additives as necessary.
  • additives such as carbon black and bengara, low stress components such as silicone oil and silicone rubber, flame retardants such as antimony trioxide, aluminum hydroxide, magnesium hydroxide, zinc borate, zinc molybdate, phosphazene, bismuth oxide Inorganic ion exchangers such as hydrates.
  • the method for obtaining a molded body from the resin composition of the present invention is not particularly limited, and molding methods such as transfer molding, injection molding, and compression molding can be used.
  • the molding conditions are appropriately set according to the purpose.
  • the molding conditions can be obtained by heat molding at a temperature of about 150 to 220 ° C. for a time of about 1 to 5 minutes.
  • the resin composition of the present invention can be used as various coating materials, and uses such as heat resistance, lamination impregnation, and metal coating are suitable.
  • the molded article of the present invention is suitable for uses such as for automobiles, OA equipment casings, and building materials.
  • Adhesiveness with Al and Cu A peel test was performed using Al foil and Cu foil on the surface of the molded body produced in each example and comparative example.
  • the test conditions are as follows. (Test conditions) About the sample shape
  • Example 1 (Extraction of lignin)
  • bamboo was used as a raw material for lignin.
  • Bamboo material cut to an appropriate size was placed in a 5 L pressure vessel of a steam explosion apparatus, 3.5 MPa of steam was injected, and left for 5 minutes. Thereafter, the container was opened, and a blasting treatment product produced by blasting at the time of opening was obtained.
  • the obtained crushed material was washed with water to remove water-soluble components, and then the remaining water was removed with a vacuum dryer. After adding 1000 ml of acetone as a lignin extraction solvent to 100 g of the obtained dried product, the mixture was stirred for 3 hours, and then the fiber material was removed by filtration. The extraction solvent was removed from the obtained filtrate to obtain steam explosion lignin.
  • the obtained steam explosion lignin was powder at room temperature (25 ° C.) and was soluble in an organic solvent. The content of sulfur atoms in the steam explosion lignin was 0.5% by mass or less. Further, steam explosion using a gel permeation chromatography (GPC) (differential thermorefractive type: RI-8020, pump: DP-8020, deaerator: SD-8022) manufactured by Tosoh Corporation equipped with a differential refractometer. The weight average molecular weight of lignin was measured.
  • GPC gel permeation chromatography
  • Polystyrene having a low polydispersity was used as a standard sample, tetrahydrofuran was used as a mobile phase, and Gel Pack GL-A120S and GL-A170S manufactured by Hitachi High-Technologies Corporation were connected in series as a column, and molecular weight measurement was performed.
  • the flow rate was 1 ml / min and the measurement temperature was 25 ° C.
  • the weight average molecular weight of the steam explosion lignin was 2400.
  • solvent solubility of lignin 1 g of the lignin was added to the following solvent group 10 ml for evaluation. A: Easily dissolved at room temperature (25 ° C.). B: Not dissolved at room temperature (25 ° C.) but dissolved at 50 to 70 ° C. C: It did not dissolve even when heated.
  • Solvent group 1 acetone, cyclohexanone, tetrahydrofuran
  • Solvent group 2 methanol, ethanol, methyl ethyl ketone The solvent solubility of the above lignin was A in solvent group 1 and B in solvent group 2.
  • Example 2 In Example 1, except having changed content of each raw material, it carried out similarly to Example 1, and obtained the resin composition, and obtained the molded object using this resin composition. The results of evaluation in the same manner as in Example 1 are shown in Table 1.
  • Example 1 except having changed content of each raw material, it carried out similarly to Example 1, and obtained the resin composition, and obtained the molded object using this resin composition.
  • the resin composition was too hard, the workability was poor, and an evaluable molded article could not be obtained. Therefore, subsequent evaluation is not performed.
  • Phenol novolac resin “HP-850N” manufactured by Hitachi Chemical Co., Ltd., softening point (ring and ball method) 83 ° C.
  • Example 1 except having changed content of each raw material, it carried out similarly to Example 1, and obtained the resin composition, and obtained the molded object using this resin composition.
  • the molded product was evaluated in the above (5). The evaluation results are shown in Table 2.
  • the resin composition of the present invention and a molded product obtained from the resin composition have a high degree of plant origin, good workability, excellent heat resistance, bending strength and tensile strength, and adhesion to metal. Therefore, it is a resin material and a molded body that can reduce the amount of fossil resources used and reduce the amount of carbon dioxide emission, and are suitable for protecting the global environment.

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

Abstract

L'invention concerne, d'une part, une composition de résine comprenant de la lignine, une résine novolac phénolique, une charge fibreuse, et un durcisseur, le rapport de masse lignine/résine novolac hénolique est étant compris entre 20/80 et 52/48, et, d'autre part, un objet moulé obtenu par moulage de la composition de résine.
PCT/JP2015/064808 2014-08-18 2015-05-22 Composition de résine et objet moulé Ceased WO2016027537A1 (fr)

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JP2014-166092 2014-08-18
JP2014166092A JP2017178973A (ja) 2014-08-18 2014-08-18 樹脂組成物及び成形体

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JP2020050814A (ja) * 2018-09-28 2020-04-02 住友ベークライト株式会社 フェノール変性リグニン樹脂を含む樹脂材料、それを用いたフェノール変性リグニン樹脂組成物および構造体
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