WO2024095521A1 - Composition durcissable - Google Patents

Composition durcissable Download PDF

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Publication number
WO2024095521A1
WO2024095521A1 PCT/JP2023/021900 JP2023021900W WO2024095521A1 WO 2024095521 A1 WO2024095521 A1 WO 2024095521A1 JP 2023021900 W JP2023021900 W JP 2023021900W WO 2024095521 A1 WO2024095521 A1 WO 2024095521A1
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WIPO (PCT)
Prior art keywords
component
area
composition
curable composition
compound
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PCT/JP2023/021900
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English (en)
Japanese (ja)
Inventor
忠明 山岸
貴洋 角田
莉久 川本
忠史 横浦
敬太朗 宮川
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本州化学工業株式会社
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Publication of WO2024095521A1 publication Critical patent/WO2024095521A1/fr

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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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
    • C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
    • C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols

Definitions

  • the present invention relates to a curable composition, a cured product obtained by curing the composition, a curing agent for resol-type phenolic resins, and an adhesive containing the curable composition.
  • Phenolic resins are polymers obtained from phenol and formaldehyde as raw materials, and are known to be classified into two types: thermoplastic novolac-type phenolic resins obtained using an acid catalyst, and thermosetting resol-type phenolic resins obtained using an alkali catalyst. Both phenolic resins are characterized by excellent heat resistance, mechanical strength, chemical resistance, and electrical insulation, and are therefore widely used in various fields such as automobile parts, insulation materials, resist materials, and adhesives. In particular, phenolic resins with high heat resistance and mechanical strength have been attracting attention in recent years as alternative materials to metals.
  • Resole-type phenolic resins have methylol groups, which are functional groups that react when heated, and crosslinks are formed by condensation of the methylol groups with hydrogen on the aromatic ring and with the methylol groups themselves when heated. This crosslinking reaction progresses everywhere, and the resol-type phenolic resin forms a random three-dimensional network to become a cured product.
  • the curing of resol-type phenolic resins that do not contain any curing accelerator is inferior to the curing of novolac-type phenolic resins in curing at low temperatures (150 to 200°C). This results in insufficient curing at low temperatures, and a cured product with excellent heat resistance cannot be obtained.
  • solutions to this problem have been proposed (for example, Patent Document 1, etc.), a satisfactory solution has not yet been found.
  • the objective of the present invention is to provide a curable composition that can be cured at low temperatures and the cured product has improved heat resistance, a cured product obtained by curing the composition, a curing agent for resol-type phenolic resins, and an adhesive containing the curable composition.
  • the present inventors investigated the possibility of obtaining a cured product with improved heat resistance by adding a curing agent to a resol-type phenolic resin to increase the reactivity of methylol groups that remain unreacted by heating alone.
  • a curing agent that is relatively flexible and has a low melting point
  • the resin would be mixed uniformly with the resol-type phenolic resin, increasing its reactivity.
  • the curing agent having a bis(hydroxyphenyl)methane skeleton was selected, and it was found that the resin could be cured at low temperatures and that the heat resistance of the cured product was improved, thereby completing the present invention.
  • a curable composition comprising the following component (A) and component (B): Component (A): A resol-type phenolic resin.
  • a cured product obtained by curing the curable composition according to 1. 3.
  • a curing agent for resol-type phenolic resins comprising the following component (B): Component (B): A composition comprising component (B1) consisting of the following compounds (1), (2), and (3), wherein the total amount of component (B1) is in the range of 40 area % to 70 area % based on the total amount of all components detected by gel permeation chromatography using a differential refractometer as a detector. 4.
  • An adhesive comprising the curable composition according to 1.
  • the curable composition of the present invention can be cured at a lower temperature than the conventionally known resol-type phenolic resins, and therefore the temperature in the molding process of the curable resin can be lowered, which enables efficiency improvement by shortening heating and cooling times and saving energy.
  • the composition can be used on materials (substrates) that are sensitive to heat, making it extremely useful.
  • the cured product of the compound of the present invention has significantly improved heat resistance compared to the cured product of a conventionally known resol-type phenolic resin cured only with resol, and is therefore a highly useful material with excellent stability and reliability at high temperatures.
  • the curable composition of the present invention and a cured product thereof can be suitably used as a resin raw material for varnishes that can be applied to various substrates, prepregs impregnated with the varnish, printed circuit boards, sealants for electronic components, electric/electronic molded components, automobile components, laminates, paints, resist inks, and the like.
  • FIG. 1 shows differential scanning calorimetry (DSC) curves for Example 5 (solid line) and Comparative Example 10 (dotted line).
  • the component (A) contained in the curable composition of the present invention is a resol type phenolic resin.
  • the resol type phenolic resin used in the present invention can be obtained by reacting a phenolic compound such as phenol, cresol, or bisphenol A with an aldehyde compound such as formaldehyde, paraformaldehyde, or glyoxal in the presence of an alkali catalyst.
  • the alkali catalyst can be an inorganic system such as an oxide or hydroxide of an alkali metal or an alkaline earth metal, or an organic system such as an amine or ammonia.
  • the resol-type phenolic resin of component (A) in the present invention is preferably one obtained by reacting a mononuclear phenolic compound such as phenol or cresol with an aldehyde compound, more preferably one obtained by reacting phenol or cresol with an aldehyde compound, and particularly preferably one obtained by reacting phenol with an aldehyde compound.
  • the weight average molecular weight (Mw) of component (A) is preferably 4,000 or more, more preferably 8,000 or more, even more preferably 12,000 or more, and particularly preferably 15,000 or more, with the upper limit being preferably 50,000 or less, more preferably 40,000 or less, even more preferably 30,000 or less, and particularly preferably 20,000 or less.
  • the weight average molecular weight (Mw)/number average molecular weight (Mn) ratio (Mw/Mn) of component (A) is preferably 3.0 or more, more preferably 6.0 or more, even more preferably 10.0 or more, and particularly preferably 15.0 or more, with the upper limit being preferably 20.0 or less, more preferably 19.0 or less, even more preferably 18.0 or less, and particularly preferably 17.0 or less.
  • Component (B) contained in the curable composition of the present invention, or component (B) contained in the curing agent for resol-type phenolic resin of the present invention is intended to cure the resol-type phenolic resin of component (A) of the present invention, and is a composition which contains component (B1) consisting of the following compounds (1), (2), and (3), and in which the total amount of component (B1) is in the range of 40 area % or more and 70 area % or less based on the total amount of all components detected by measurement by gel permeation chromatography using a differential refractometer as a detector.
  • the component (B) in the present invention preferably contains the component (B1) consisting of the above-mentioned compounds (1), (2) and (3) in a total amount, as measured by the gel permeation chromatography, in the range of 50 area % or more and 67 area % or less, and more preferably in the range of 53 area % or more and 65 area % or less.
  • component (B1) consisting of compound (1), compound (2), and compound (3) preferably contains compound (1)/compound (2) in an area ratio of 35/65 to 55/45, and more preferably 40/60 to 50/50, based on measurement of compound (1) and compound (2) at a wavelength of 280 nm by high performance liquid chromatography using an ultraviolet absorptiometer as a detector.
  • component (B1) in the present invention preferably contains the sum of compound (1) and compound (2) and compound (3) in an area ratio of compound (1) + compound (2) / compound (3) of 95/5 to 80/20, and more preferably an area ratio of 90/10 to 85/15, based on measurement at a wavelength of 280 nm by high performance liquid chromatography using an ultraviolet absorptiometer as a detector.
  • the component (B) in the present invention can be obtained by reacting phenol with formaldehyde in the presence of an acid catalyst, setting the amount of phenol to be used in the range of 3 to 8 moles per mole of formaldehyde, and removing unreacted phenol and the like from the resulting reaction mixture by distillation or the like. After the reaction, neutralization treatment and washing with water to remove neutralization salts may be performed as necessary.
  • the amount of phenol used in the reaction is preferably in the range of 3.7 to 7.2 moles, more preferably in the range of 4.3 to 6.7 moles, per mole of formaldehyde.
  • the acid catalyst is preferably oxalic acid, and when an oxalic acid catalyst is used, it is preferable to produce component (B) by removing low boiling point substances such as phenol by distillation directly from the obtained reaction mixture.
  • the amount of oxalic acid used is preferably in the concentration range of 1 to 0.01% by weight, more preferably 0.5 to 0.05% by weight, based on the total amount of phenol and formaldehyde used in the reaction.
  • the reaction temperature is preferably 60 to 100°C, more preferably 70 to 90°C.
  • the component (B) of the present invention prepared by such a production method contains, in addition to the component (B1), a polycondensate of a phenol other than the component (B1) and formaldehyde.
  • the polycondensate preferably contains the component (B2) described below, more preferably contains the components (B2) and (B3), and further preferably contains the components (B2), (B3) and (B4).
  • Components (B2) to (B4) are described in detail below.
  • Component (B2) contained in component (B) in the present invention is a group of compounds represented by the following general formula (b2) which are produced by substituting a (4-hydroxyphenyl)methyl group or a (2-hydroxyphenyl)methyl group at the para-position or ortho-position of the hydroxyl group in the above-mentioned compounds (1), (2), and (3).
  • the bonding position of the methylene group is the para-position or ortho-position of the hydroxyl group.
  • Examples of the compound represented by the above general formula (b2) include the compounds shown below.
  • component (B2) contained in component (B) in the present invention is preferably 20 to 30 area %, more preferably 22 to 28 area %, and even more preferably 24 to 26 area %, based on the total amount of all components detected by gel permeation chromatography using a differential refractometer as a detector.
  • Component (B3) and Component (B4) > Component (B3) that may be contained in component (B) in the present invention consists of a group of compounds having a structure in which a (4-hydroxyphenyl)methyl group or a (2-hydroxyphenyl)methyl group is substituted at the para-position or ortho-position of the hydroxyl group of the compound represented by general formula (b2) above.
  • component (B4) which may be contained in component (B) in the present invention consists of a group of compounds having a structure in which a (4-hydroxyphenyl)methyl group or a (2-hydroxyphenyl)methyl group is substituted at the para- or ortho-position of the hydroxyl group of the compound contained in component (B3), and a group of compounds having a structure obtained by repeating a reaction one or more times in which the obtained compound is further substituted with a (4-hydroxyphenyl)methyl group or a (2-hydroxyphenyl)methyl group.
  • the component (B) in the present invention may contain, in addition to the components (B1) and (B2), the component (B3) and/or the component (B4).
  • component (B) in the present invention contains components (B3) and (B4)
  • the content of component (B3) is preferably in the range of 18 to 28 area %, more preferably in the range of 20 to 26 area %, even more preferably in the range of 21 to 25 area %, and particularly preferably 22 to 24.5 area %, based on the total content (area %) of components (B2), (B3), and (B4) detected by measurement by gel permeation chromatography using a differential refractometer as a detector.
  • the molecular weight of component (B2) is preferably in the range of 440 to 490, more preferably in the range of 450 to 480, and the molecular weight of component (B3) is preferably in the range of 580 to 630, more preferably in the range of 590 to 620.
  • the curable composition of the present invention contains a resol type phenolic resin as component (A) and component (B), and component (B) is contained as a curing agent in an amount of preferably 1 to 25 parts by weight, more preferably 5 to 20 parts by weight, and even more preferably 8 to 13 parts by weight, per 100 parts by weight of the resol type phenolic resin (A).
  • the curable composition of the present invention is preferably obtained by mixing the resol type phenolic resin of component (A) with component (B) in a temperature environment of about 90° C. within a time period of about 10 minutes.
  • the curable composition of the present invention may contain materials such as inorganic fillers such as silicon oxide, aluminum oxide, magnesium oxide, boron nitride, aluminum nitride, silicon nitride, silicon carbide, and hexagonal boron nitride, and reinforcing fibers such as carbon fiber, glass fiber, organic fiber, boron fiber, steel fiber, and aramid fiber.
  • the amount of the above-mentioned materials that can be used in combination in the curable composition of the present invention is preferably within a range of 0.01 to 100 parts by weight per 1 part by weight of the total of the resol type phenolic resin of component (A) and component (B).
  • the curable composition of the present invention is preferably subjected to a vacuum degassing treatment as a pretreatment to prevent bubbles from being generated during curing if the composition contains water or residual solvent.
  • the temperature of the vacuum degassing treatment is not particularly limited as long as the curable composition of the present invention is in a molten state, but it is preferable to perform the treatment at an upper limit of 90°C because the curing does not proceed and degassing is easy.
  • the pressure of the vacuum degassing treatment is not particularly limited, but it is better to perform it at a low pressure (high degree of vacuum), and it may be performed either in air or in a nitrogen-substituted atmosphere. The vacuum degassing treatment is performed until bubbles cannot be visually confirmed.
  • the cured product of the present invention can be obtained by curing the curable composition of the present invention containing the resol type phenolic resin of component (A) and component (B).
  • methods for producing the cured product of the present invention include a method in which the material is heated to a predetermined temperature to be cured, a method in which the material is heated and melted and poured into a mold or the like and the mold is further heated to be cured and molded, and a method in which the molten material is poured into a preheated mold and cured.
  • the curable composition of the present invention is usually cured at a curing temperature in the range of 140 to 220°C, preferably in the range of 150 to 200°C, more preferably in the range of 160 to 190°C, and even more preferably in the range of 165 to 185°C.
  • the reaction time may be about 5 to 30 minutes.
  • the curable composition of the present invention has a lower curing temperature than conventionally known resol-type phenolic resins, and therefore can be used for materials (substrates) that are sensitive to heat, and is very useful, since it can be made more efficient by shortening the heating and cooling time and saving energy in the molding process of the curable resin.
  • the cured product has a significantly improved heat resistance compared to conventionally known cured products, and is therefore a material that is excellent in stability and reliability at high temperatures, and is very useful.
  • the curable composition of the present invention can cause the curing reaction to proceed and be completed at a lower temperature than conventional ones, and therefore can be suitably used as an adhesive, a sealant, a coating material, a sizing agent, etc. Furthermore, the cured product of the curable composition of the present invention can be suitably used in fields requiring ultra-heat resistance and good dielectric properties (e.g., electronic information devices, home appliances, automobiles, precision machinery, aircraft, space industry equipment, etc.).
  • ⁇ Analysis method> Gel permeation chromatography for analyzing the concentrations of components (B1) to (B4): GPC
  • the components (B1) to (B4) contained in the component (B) of the present invention are identified by the area percentages of all the components detected by this analysis.
  • High performance liquid chromatography measurement Measurement equipment: High-performance liquid chromatography analyzer (UFLC) (manufactured by Shimadzu Corporation) Pump: LC-20AD Column oven: CTO-20A Detector: SPD-20A (UFLC), cell length 5 mm Column: HALO-C18 (column 3.0 x 75 mm, particle size 2.7 ⁇ m, manufactured by Advanced Materials Technology) [Measurement condition] Oven temperature: 50°C Flow rate: 0.8 mL/min.
  • UFLC High-performance liquid chromatography analyzer
  • SPD-20A SPD-20A
  • Oven temperature 50°C Flow rate: 0.8 mL/min.
  • Thermogravimetric analysis (TGA) Equipment SII NanoTechnology's differential thermal and thermogravimetric simultaneous measurement equipment (TG/DTA6200) 5.0 mg to 7.0 mg of the cured product was placed in an aluminum pan for DSC, and the temperature was increased from 100° C. to 600° C. at a rate of 10° C./min in a nitrogen atmosphere. The 5% weight loss temperature (Td5%) of the cured product during the temperature rise process was measured.
  • GPC Measurement device High-performance liquid chromatography analyzer (Chromaster 5110) manufactured by Hitachi High-Tech Science Co., Ltd. Column oven: Chromaster 5310 (Hitachi High-Tech Science Co., Ltd.) UV detector: Chromaster 5410 (Hitachi High-Tech Science Co., Ltd.) Column: Shodex styrene-divinylbenzene copolymer packed column (LF-804 x 2) Other: GL Science degassing unit (DG660B) [Measurement condition] Flow rate: 1.0 mL/min.
  • composition (B'-1) different from the component (B) of the present invention was obtained as the residual liquid.
  • the content of component (B1) was 32.7 area % (less than 40 area %)
  • the content of component (B2) was 23.3 area %
  • the content of component (B3) was 14.9 area %
  • the content of component (B4) was 29.1 area %.
  • the composition of component (B1) as determined by HPLC was 14.2 area % of compound (1), 14.5 area % of compound (2), and 3.2 area % of compound (3).
  • composition (B-1) of component (B) was obtained as the residual liquid.
  • the content of component (B1) was 56.7 area %
  • the content of component (B2) was 25.0 area %
  • the content of component (B3) was 10.5 area %
  • the content of component (B4) was 7.8 area %.
  • component (B1) as determined by HPLC was 20.9 area % of compound (1), 26.6 area % of compound (2), and 6.7 area % of compound (3).
  • the polystyrene-equivalent molecular weights measured by GPC were 313 for component (B1), 457 for component (B2), and 593 for component (B3).
  • composition (B-2) of component (B) was obtained as a residual liquid.
  • the content of component (B1) was 62.0 area %
  • the content of component (B2) was 24.5 area %
  • the content of component (B3) was 8.4 area %
  • the content of component (B4) was 5.1 area %.
  • component (B1) as determined by HPLC was 22.1 area % of compound (1), 30.6 area % of compound (2), and 8.5 area % of compound (3).
  • the polystyrene-equivalent molecular weights measured by GPC were 324 for component (B1), 474 for component (B2), and 611 for component (B3).
  • composition (B'-3) obtained in Production Example 4 was added to 1.00 g of the mixture obtained in Production Example 1, and the mixture was gradually heated to 130 to 180°C to melt, and then cooled to obtain composition (B'-4) which is different from component (B).
  • the content of component (B1) was 75.3 area %
  • the content of component (B2) was 15.5%
  • the content of component (B3) was 5.5%
  • the content of component (B4) was 3.7%.
  • Example 1 0.9 g of a commercially available resol type phenolic resin (manufactured by Sumitomo Bakelite Co., Ltd.) was added to a 10 mL sample tube, and 0.1 g of composition (B-1) of component (B) with a content of component (B1) of 56.7 area % obtained in Production Example 3 was added thereto.
  • This sample tube was heated in an oil bath at 90°C for 10 minutes while stirring and mixed.
  • the mixed composition was cooled to room temperature and then heated at 170°C for 10 minutes to obtain a cured product.
  • the Td5% of the resulting cured product was measured.
  • the commercially available resol type phenolic resin used was confirmed by GPC measurement to have a number average molecular weight (Mn) of 960 and a weight average molecular weight (Mw) of 16,000.
  • Example 2 A cured product was obtained by heating in the same manner as in Example 1, except that the curing temperature was 180°C. The Td5% of the resulting cured product was measured.
  • Example 3 A cured product was obtained by heating in the same manner as in Example 2, except that 0.1 g of composition (B-2) of component (B) containing 62.0 area % of component (B1) obtained in Production Example 5 was added instead of adding 0.1 g of composition (B-1) of component (B) containing 56.7 area % of component (B1). The Td5% of the resulting cured product was measured.
  • Example 4 A cured product was obtained by heating in the same manner as in Example 1, except that the curing temperature was 200°C. The Td5% of the resulting cured product was measured.
  • ⁇ Comparative Examples 1 to 3> 1.0 g of the same commercially available resol-type phenolic resin as in Example 1 was used, and cured products were obtained by heating in the same manner as in Example 1, except that the composition of component (B) was not added and curing was carried out at temperatures of 170° C. (Comparative Example 1), 180° C. (Comparative Example 2), and 200° C. (Comparative Example 3). The Td5% of each of the resulting cured products was measured.
  • ⁇ Comparative Example 4> A cured product was obtained by heating in the same manner as in Example 1, except that 0.1 g of composition (B'-1) obtained in Production Example 1, which had a component (B1) content of 32.7%, was added instead of adding 0.1 g of composition (B-1) of component (B) containing 56.7% of component (B1). The Td5% of the resulting cured product was measured.
  • Example 5 A cured product was obtained by heating in the same manner as in Example 1, except that 0.1 g of composition (B'-2) obtained in Production Example 2, which had a component (B1) content of 13.3%, was added instead of adding 0.1 g of composition (B-1) of component (B) containing 56.7% of component (B1). The Td5% of the resulting cured product was measured.
  • Comparative Example 9 A composition was prepared in the same manner as in Comparative Example 8, except that the mixed composition was heated at 170° C. for 10 minutes without cooling to obtain a cured product. The Td5% of the obtained cured product was measured and found to be 366° C.
  • curable composition of the present invention is very useful because it can be used for materials (substrates) that are sensitive to heat.
  • Example 5 0.9 g of a commercially available resol type phenolic resin (manufactured by Sumitomo Bakelite Co., Ltd.) and 0.1 g of the composition (B-1) of component (B) obtained in Production Example 3, in which the content of component (B1) was 56.7 area %, were mixed and cooled in the same manner as in Example 1. The obtained mixture was measured using a differential scanning calorimeter under the above-mentioned measurement conditions.
  • a commercially available resol type phenolic resin manufactured by Sumitomo Bakelite Co., Ltd.
  • DSC Differential scanning calorimetry
  • Example 5 had a calorific value ( ⁇ H) of 192 J/g and a peak top temperature of 200°C, while Comparative Example 10 had a calorific value ( ⁇ H) of 216 J/g and a peak top temperature of 202°C. From these results, it was revealed that the curable composition of the present invention can be cured in a short time with less heat generation compared to the conventionally known resol-type phenolic resins, and therefore the curable composition of the present invention can be highly useful because it can reduce the heating and cooling time and save energy.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

La présente invention aborde le problème consistant à fournir : une composition durcissable qui peut être durcie dans des conditions de basse température et un produit durci dont la résistance à la chaleur est améliorée ; un produit durci obtenu par durcissement de ceux-ci ; un agent de durcissement pour une résine phénolique de type résol ; et un adhésif contenant une composition durcissable. La solution de l'invention porte sur une composition durcissable contenant le composant (A) suivant et le composant (B) suivant.　Le composant (A) est une résine phénolique de type résol. Le composant (B) est une composition comprenant un composant (B1) constitué du composé (1), du composé (2) et du composé (3), la quantité totale du composant (B1) se situant dans la plage de 40 % en surface à 70 % en surface de la quantité totale de tous les composants détectés par chromatographie de perméation sur gel à l'aide d'un réfractomètre différentiel.
PCT/JP2023/021900 2022-11-01 2023-06-13 Composition durcissable WO2024095521A1 (fr)

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JP2022175335 2022-11-01
JP2022-175335 2022-11-01

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3870670A (en) * 1972-06-19 1975-03-11 Reichhold Albert Chemie Ag Process for the manufacture of dispersions of thermosetting reaction products
JP2003286387A (ja) * 2002-03-28 2003-10-10 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグおよび紙基材フェノール樹脂積層板
JP2005154613A (ja) * 2003-11-27 2005-06-16 Sumitomo Bakelite Co Ltd 液状フェノール樹脂組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3870670A (en) * 1972-06-19 1975-03-11 Reichhold Albert Chemie Ag Process for the manufacture of dispersions of thermosetting reaction products
JP2003286387A (ja) * 2002-03-28 2003-10-10 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグおよび紙基材フェノール樹脂積層板
JP2005154613A (ja) * 2003-11-27 2005-06-16 Sumitomo Bakelite Co Ltd 液状フェノール樹脂組成物

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