CN116457412A - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- CN116457412A CN116457412A CN202180077135.6A CN202180077135A CN116457412A CN 116457412 A CN116457412 A CN 116457412A CN 202180077135 A CN202180077135 A CN 202180077135A CN 116457412 A CN116457412 A CN 116457412A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- water
- resin
- mass
- polyvinyl alcohol
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- 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
Landscapes
- 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)
Abstract
A resin composition comprising a water-soluble resole, polyvinyl alcohol, and water, the resin composition characterized in that: the resin composition is in the form of an aqueous solution in which the water-soluble resol-type phenolic resin and the polyvinyl alcohol are dissolved in the water, and the polyvinyl alcohol is present in an amount of more than 0% by mass and not more than 30% by mass relative to the total solid content of the resin composition.
Description
Technical Field
The present invention relates to a resin composition comprising a water-soluble resol-type phenolic resin.
Background
Phenolic resins used for impregnation of honeycomb cores, adhesive applications of wet friction materials, and the like have been used as solvent-based phenolic resins using alcohols and the like, in view of their impregnation properties and the properties of coated surfaces (for example, patent document 1). In recent years, from the viewpoint of safety, it has been demanded to reduce the amount of a flammable solvent and from the viewpoint of preventing environmental pollution, and therefore, these solvent-based compositions have been gradually replaced with dispersion-type or aqueous emulsion-type products, and studies on water-soluble phenol resins have been actively conducted.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2014-24881
Disclosure of Invention
Technical problem to be solved by the invention
However, there are cases where the water-soluble phenol resin is inferior in heat resistance, handleability, and the like, and it is problematic in use. In addition, although some studies and practical use of the emulsified phenolic resin have been made, in the case of using the emulsified phenolic resin, there are the following disadvantages: the surface properties are poor, and the performance of the phenolic resin is lowered by emulsion stabilizers, suspending agents, and the like.
Means for solving the technical problems
The present invention has been made in view of the above-described problems, and an object of the present invention is to provide a phenolic resin composition which can be provided in the form of an aqueous solution, does not cause a problem of volatilization of an organic solvent, and can improve heat resistance.
According to the present invention, there is provided a resin composition comprising a water-soluble resole, polyvinyl alcohol and water, the resin composition characterized in that:
the resin composition is in the form of an aqueous solution formed by dissolving the water-soluble resol-type phenolic resin and the polyvinyl alcohol in the water,
the polyvinyl alcohol is present in an amount of more than 0% by mass and 30% by mass or less relative to the total solid content of the resin composition.
Effects of the invention
According to the present invention, a phenolic resin composition having high heat resistance and reduced environmental load and load on the human body can be provided because it does not contain an organic solvent.
Detailed Description
Hereinafter, embodiments of the present invention will be described. In the present specification, the expression "a to b" in the description of the numerical range means "a or more and b or less" unless otherwise specified. For example, "5 to 90 mass%" means "5 mass% or more and 90 mass% or less".
[ resin composition ]
The resin composition of the present embodiment contains a water-soluble resol, polyvinyl alcohol, and water. The resin composition of the present embodiment is provided in the form of an aqueous solution of these water-soluble resol resin and polyvinyl alcohol dissolved in water. In the resin composition of the present embodiment, the content of polyvinyl alcohol is an amount of more than 0% by mass and 30% by mass or less relative to the total solid content of the resin composition.
The resin composition of the present embodiment is in the form of an aqueous solution of a water-soluble resol resin and polyvinyl alcohol dissolved in water. Since the resin composition of the present embodiment does not contain an organic solvent, volatilization of the organic solvent does not occur, and thus there is little or no load on the environment or on the human body during handling and use.
The resin composition of the present embodiment contains a water-soluble resol-type phenolic resin and polyvinyl alcohol, and the amount of polyvinyl alcohol is more than 0 mass% and 30 mass% or less, preferably 1 mass% or more and 25 mass% or less, more preferably 2 mass% or more and 20 mass% or less, and still more preferably 4 mass% or more and 15 mass% or less, relative to the total solid content of the resin composition. The resin composition of the present embodiment can maintain the heat resistance of the water-soluble resol resin and has flexibility suitable for use by containing the polyvinyl alcohol in the above-described amount. Therefore, the adhesive resin composition is excellent in handling properties when used as an adhesive for friction materials or a binder resin material for impregnation of a base material. Further, since the resin composition has high adhesive strength by containing polyvinyl alcohol, it can be suitably used as an adhesive for a friction material, for example. Further, since the resin composition contains polyvinyl alcohol, it is flexible, and thus when used as a binder resin material for impregnation of a base material, for example, a molded article having flexibility and excellent mechanical strength can be obtained.
The components contained in the resin composition according to the present embodiment will be described below.
(Water-soluble resol-type phenolic resin)
The water-soluble resol resin used in the adhesive composition of the present embodiment is a resin obtained by reacting phenols and aldehydes in a reaction solvent under predetermined conditions described below in the presence of an alkaline catalyst.
Examples of phenols used for synthesizing the water-soluble resol resin used in the present embodiment include: phenol; cresols such as o-cresol, m-cresol, and p-cresol; ethylphenols such as o-ethylphenol, m-ethylphenol and p-ethylphenol; butylphenols such as isopropyl phenol, butylphenol, and p-tert-butylphenol; alkylphenols such as p-tert-pentylphenol, p-octylphenol, p-nonylphenol and p-cumylphenol; halogenated phenols such as fluorophenol, chlorophenol, bromophenol and iodophenol; monohydric phenol substituents such as p-phenylphenol, aminophenol, nitrophenol, dinitrophenol, trinitrophenol, etc.; and monohydric phenols such as 1-naphthol and 2-naphthol; resorcinol, alkyl resorcinol, pyrocatechol, catechol, alkyl catechol, hydroquinone, alkyl hydroquinone, phloroglucinol, bisphenol a, bisphenol F, bisphenol S, polyhydric phenols such as dihydroxynaphthalene, and the like. These may be used alone or in combination of 2 or more.
Examples of aldehydes used for synthesizing the water-soluble resol resin used in the present embodiment include formaldehyde, paraformaldehyde, trioxane, acetaldehyde, propionaldehyde, polyoxymethylene, chloral, hexamethylenetetramine, furfural, glyoxal, n-butyraldehyde, hexanal, allylaldehyde, benzaldehyde, crotonaldehyde, acrolein, tetra-formaldehyde, phenylacetaldehyde, o-tolualdehyde, salicylaldehyde, and the like. These may be used alone or in combination of 2 or more. In addition, precursors of these aldehydes or solutions of these aldehydes may also be used. Among them, from the viewpoint of manufacturing cost, an aqueous formaldehyde solution is preferably used.
Examples of the basic catalyst used for synthesizing the water-soluble resol resin used in the present embodiment include: hydroxides of alkali metals or alkaline earth metals such as sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates such as sodium carbonate and calcium carbonate; oxides such as lime; sulfite such as sodium sulfite; phosphates such as sodium phosphate; amines such as ammonia, trimethylamine, triethylamine, monoethanolamine, diethanolamine, triethanolamine, hexamethylenetetramine and pyridine.
The reaction solvent used for synthesizing the water-soluble resol resin used in the present embodiment is generally water, but an organic solvent may be used. Specific examples of such organic solvents include alcohols, ketones, and aromatics. Specific examples of the alcohols include methanol, ethanol, propanol, ethylene glycol, diethylene glycol, triethylene glycol, and glycerin. Specific examples of ketones include acetone and methyl ethyl ketone. Specific examples of the aromatic compound include toluene and xylene.
Examples of the form of the resol include solid, aqueous solution, solvent solution and aqueous dispersion. In the case of using an organic solvent as a reaction solvent for synthesizing the water-soluble resol resin, the organic solvent may be removed from a reaction solution containing a reaction product by a known method such as extraction and drying.
The resol resin used in the present embodiment can be obtained by adding the phenol (P) and the aldehyde (F) to a reaction vessel at a molar ratio (F/P) of 0.8 or more, preferably 0.8 or more and 3.0 or less, more preferably 1.0 or more and 2.8 or less, still more preferably 1.2 or more and 2.5 or less, further adding the above-mentioned basic catalyst as a polymerization catalyst, and refluxing for a suitable period of time (for example, 3 to 6 hours). When the molar ratio (F/P) of the phenol (P) to the aldehyde (F) is less than 0.8, the weight average molecular weight of the resulting water-soluble resol is small, and the resulting water-soluble resol may not have desired heat resistance. If the molar ratio (F/P) of the phenol (P) to the aldehyde (F) is greater than 3.0, gelation of the resin tends to proceed during the reaction, and therefore the reaction efficiency is lowered, and a water-insoluble high molecular weight resol is produced, which is not preferable. The reaction temperature is, for example, 40℃to 120℃and preferably 60℃to 100 ℃. Thus, gelation can be suppressed to obtain a water-soluble resol resin having a target molecular weight. The weight average molecular weight of the water-soluble resol is preferably 250 to 3000, more preferably 300 to 2000. The resol having the molecular weight in the above range has water solubility and has high heat resistance.
The content of the methylol phenol contained in the resol resin is, for example, more than 0 mass% and 20 mass% or less. The adhesive composition of the present embodiment can further improve heat resistance while maintaining moderate adhesion by containing the resol resin having the content of methylol phenol in the above range.
Herein, the methylol phenol contained in the resol resin means a methylolated mononuclear body of phenol which is produced as a by-product in the synthesis of the resol resin in which phenol and aldehyde are reacted with each other in the presence of a basic catalyst. The methylolated mononuclear body of the phenol comprises: monohydric methyl phenols; dimethylol phenols; trimethylol phenols; and mixtures thereof.
The methylol phenol present in the resol resin can be reduced or removed by reacting the phenol and the aldehyde in the presence of an acidic catalyst to synthesize a novolak-type phenol resin, and then reacting the novolak-type phenol resin with the aldehyde in the presence of a basic catalyst.
(polyvinyl alcohol)
Examples of the polyvinyl alcohol used in the adhesive composition of the present embodiment include polyvinyl alcohol (PVA), cationic modified polyvinyl alcohol (cationic modified PVA), and anionic modified polyvinyl alcohol (anionic modified PVA). Polyvinyl alcohol (PVA) is an unmodified homopolymer type. Examples of commercial products of PVA include gossenol series (GL-03, EG-05, EG-30, EG-40, etc.) manufactured by japan synthetic chemicals (Nippon Synthetic Chemical co., ltd.), and Poval (PVA) series (403, 405, 420H, 424H, 203, 205, 210, 217, 220, 224, 235, 217E, 220E, 224E, etc.) manufactured by KURARAY co., ltd.
The saponification degree of polyvinyl alcohol (PVA) is preferably 85% or more, more preferably 90% or more, and still more preferably 95% or more. When the saponification degree is not less than the above lower limit, the handleability of the obtained resin composition can be improved.
(other Components)
The resin composition of the present embodiment may contain other additives such as flame retardants, coupling agents, antioxidants, and colorants in addition to the above components within a range that does not impair the effects of the present invention.
[ method for producing resin composition ]
The phenolic resin composition of the present embodiment can be produced by mixing the above components with water by a known method and dissolving the mixture in water to prepare an aqueous solution.
The resin composition of the present embodiment is provided in the form of an aqueous solution having a solid content of 10 mass% to 80 mass%. The amount of the solid component of the resin composition of the present embodiment can be adjusted according to the use of the resin composition by adjusting the amount of water as a solvent. For example, when the resin composition of the present embodiment is used as an adhesive for a friction material, the solid content is preferably 50 to 80 mass%. The viscosity of the resin composition thus obtained is suitable for application to a friction substrate, and sufficient joint strength for use as a friction material can be obtained. When the resin composition of the present embodiment is used for impregnation of a substrate, the solid content is preferably 10 to 70% by mass. Thus, a resin composition having excellent handleability and excellent impregnation properties can be obtained, and thus a molded article having high strength and high quality can be produced with excellent production efficiency.
[ use of resin composition ]
The resin composition of the present embodiment can be used as an adhesive for a friction material in the form of an aqueous solution or varnish. Alternatively, the resin composition of the present embodiment may be impregnated into an inorganic fiber base material such as a honeycomb core, and used for producing an inorganic fiber composite.
The resin composition of the present embodiment may be provided or stored in the form of a solid from which the aqueous solvent is removed by drying. Examples of the solid form include a block form, a flat plate form, a sheet form, and a film form.
When the resin composition of the present embodiment is provided as a solid, the content of the methylol phenol in the resol is, for example, 3.0 mass% or less, preferably 2.0 mass% or less, and more preferably 1.0 mass% or less. The lower limit of the content of the resol is not particularly limited, but is, for example, 0.01 mass% or more. The content of methylol phenol in the resol resin in the above range can reduce the tackiness of the resol resin, and thus can suppress the surface tackiness of a solid formed from a resin composition containing the resol resin. As a result, even when a plurality of resin compositions in solid form are stored in an overlapping manner before shipment or before use, it is possible to prevent a problem that the resin solids are stuck to each other and are difficult to separate.
In the case where the resin composition of the present embodiment is provided in the form of a solid, the liquid resin composition can be molded into a desired shape. For example, the resin composition of the present embodiment may be molded into a sheet having a thickness of 5 μm to 200 μm and a width of 10mm to 200 cm. The resin composition of the present embodiment is formed into a solid such as a sheet, and thus can be stored and transported easily.
The step of molding the resin composition into a solid form may be performed by applying a liquid resin composition onto a sheet-like substrate, and then heating and drying the resin composition to remove water and form a resin layer. The conditions for heat drying may be any conditions under which water as a solvent can volatilize, and for example, the drying is performed at a temperature of 150 to 180℃for a period of 1 to 90 minutes.
The resin layer obtained as described above can be brought into a semi-cured (B-stage) state by further heat treatment. As the heat treatment for bringing the substrate into a semi-cured state, conditions of a temperature of 100 to 200 ℃ and a time of 1 to 60 minutes can be used.
The sheet-like substrate is not particularly limited as long as it can withstand the above-mentioned heat-drying conditions, and for example, polyester-based films, polypropylene-based films, polyimide-based films, polyamide-based films, polysulfone-based films, polyether-ketone-based films, and the like can be used. The surface of the sheet-like substrate may be treated with a release agent. The base sheet may be removed after the resin layer is formed. The resin sheet thus obtained may be provided with a protective sheet on the surface opposite to the surface facing the base sheet. As the protective sheet, a sheet similar to the base sheet can be used.
While the embodiments of the present invention have been described above, these are examples of the present invention, and various configurations other than the above may be adopted.
Examples (example)
Hereinafter, the present invention will be described with reference to examples and comparative examples, but the present invention is not limited to these examples.
Example 1
To a reaction apparatus having a stirring device, a reflux condenser and a thermometer, 1000 parts by weight of phenol, 1638 parts by weight of 37% aqueous formalin (F/P molar ratio=1.9) and 30 parts by weight of sodium hydroxide were added, and the mixture was reacted at 90 ℃ for 70 minutes. The content of methylolated phenol in the obtained reaction mixture was 15.2 mass% as calculated by GPC measurement. After 780 parts by weight of water was added to the reaction mixture, 180 parts by weight of polyvinyl alcohol having a saponification degree of 99% was added at 80℃and dissolved, whereby a resin composition having a nonvolatile content of 45% and a polyvinyl alcohol content of 12% in the solid content was obtained.
Example 2
The same operation as in example 1 was performed except that the amount of polyvinyl alcohol added was 85 parts by weight and the amount of water added was 680 parts by weight, whereby a resin composition having a nonvolatile content of 45% and a solid content of 6% was obtained. The content of methylolated phenol in the reaction mixture was 13.9 mass%.
Example 3
The same operation as in example 1 was performed, except that 1000 parts by weight of phenol in example 1 was changed to novolak type phenol resin (PR-53195 manufactured by sumitomo bakelite corporation (Sumitomo Bakelite co., ltd.) containing less than 1% of free phenol, and that a 37% aqueous formalin solution was changed to 300 parts by weight, to obtain a resol type phenol resin having a methylolated phenol content of 0.3%. By using this reaction mixture, polyvinyl alcohol was dissolved in the same manner as in example 1, whereby a resin composition having a nonvolatile content of 40% and a polyvinyl alcohol content of 12% in the solid content was obtained.
Comparative example 1
The same operation as in example 1 was performed except that polyvinyl butyral was not added and the amount of water added was 500 parts by weight, whereby a resin composition having a nonvolatile content of 45% and a solid content of 0% of polyvinyl alcohol was obtained.
< evaluation of resin composition >
The physical properties of the resin composition obtained above were evaluated as follows.
(adhesive Strength)
The curing conditions were 180℃for 30 minutes, and the adhesive shear strength was measured by using an iron plate as the material to be bonded in accordance with JIS K6850. The results are shown in table 1 below.
(Heat resistance Strength)
After the test piece for the adhesive shear test was produced, the test piece was subjected to a heat treatment at 250 ℃ for 30 minutes, and then the adhesive shear strength was measured by using an iron plate as an adhesive material according to JISK 6850. The results are shown in table 1 below.
(tackiness)
The resin composition was applied to the surface of the iron plate as a base material so that the film thickness at the time of drying became about 10 μm, and heated at 80℃for 30 minutes, whereby a resin layer was formed on the surface of the base material. The tackiness of the resin layer was evaluated according to the following criteria.
The method comprises the following steps: after the resin layer is overlapped with the iron plate and left to stand for 1 hour, when the upper iron plate is lifted, the lower iron plate is also attached and lifted.
The method is free of: after the resin layer is overlapped with the iron plates and left to stand for 1 hour, when the upper iron plate is lifted, the lower iron plate is not attached and only the upper iron plate is lifted.
TABLE 1
The resin composition of the example is excellent in heat resistance and has high heat resistance strength. The sheet made of the resin composition of example 3 had no surface tackiness and was excellent in handling property during storage.
The present application claims priority based on japanese patent application publication No. 2020-192188, 11/19/2020, and the entire disclosure thereof is incorporated herein.
Claims (5)
1. A resin composition comprising a water-soluble resole, polyvinyl alcohol, and water, the resin composition characterized in that:
the resin composition is in the form of an aqueous solution formed by dissolving the water-soluble resol-type phenolic resin and the polyvinyl alcohol in the water,
the polyvinyl alcohol is present in an amount of more than 0% by mass and 30% by mass or less relative to the total solid content of the resin composition.
2. The resin composition according to claim 1, wherein:
the water-soluble resol resin has a methylol phenol content of 20 mass% or less relative to the water-soluble resol resin.
3. The resin composition according to claim 1 or 2, characterized in that:
the water-soluble resol resin has a methylol phenol content of 3.0 mass% or less relative to the water-soluble resol resin.
4. A resin composition according to any one of claims 1 to 3, characterized in that:
the saponification degree of the polyvinyl alcohol is more than 85%.
5. The resin composition according to any one of claims 1 to 4, characterized in that:
the solid content is 10 to 80 mass%.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020192188 | 2020-11-19 | ||
| JP2020-192188 | 2020-11-19 | ||
| PCT/JP2021/037858 WO2022107505A1 (en) | 2020-11-19 | 2021-10-13 | Resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116457412A true CN116457412A (en) | 2023-07-18 |
Family
ID=81708953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180077135.6A Pending CN116457412A (en) | 2020-11-19 | 2021-10-13 | Resin composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP7168121B1 (en) |
| CN (1) | CN116457412A (en) |
| WO (1) | WO2022107505A1 (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124554A (en) * | 1977-02-03 | 1978-11-07 | Union Carbide Corporation | Post-formed aqueous phenolic resin dispersions |
| US5200455A (en) * | 1992-01-30 | 1993-04-06 | Lord Corporation | Aqueous adhesive compositions containing stabilized phenolic resins |
| AU6138596A (en) * | 1995-06-27 | 1997-01-30 | Tsuyoshi Kono | Binder |
| DE10062266A1 (en) * | 2000-12-14 | 2002-07-04 | Henkel Kgaa | Aqueous single-layer rubber-metal binders |
| US20060041059A1 (en) * | 2003-02-12 | 2006-02-23 | Nok Corporation | Water-based vulcanizable adhesive composition |
| JP6044820B2 (en) * | 2012-07-24 | 2016-12-14 | Dic株式会社 | Adhesive composition and wet friction plate |
| JP2020172582A (en) * | 2019-04-10 | 2020-10-22 | 住友ベークライト株式会社 | Adhesive composition for wet friction material and wet friction plate |
-
2021
- 2021-10-13 JP JP2022505567A patent/JP7168121B1/en active Active
- 2021-10-13 WO PCT/JP2021/037858 patent/WO2022107505A1/en active Application Filing
- 2021-10-13 CN CN202180077135.6A patent/CN116457412A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7168121B1 (en) | 2022-11-09 |
| JPWO2022107505A1 (en) | 2022-05-27 |
| WO2022107505A1 (en) | 2022-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10259902B2 (en) | Resol phenolic resin for friction material, method for producing the same, adhesive for friction material, and wet friction plate | |
| JP2014208769A (en) | Resin composition for wet friction material, phenolic resin for wet friction material, and wet friction material | |
| JP7172422B2 (en) | Adhesive composition for wet friction material | |
| JP2009067921A (en) | Oil-modified phenolic resin emulsion | |
| CN116457412A (en) | Resin composition | |
| JP2008189749A (en) | Phenolic resin for wet type paper friction material, and wet type paper friction material | |
| CN114599757B (en) | Adhesive composition for wet friction material | |
| CN116457382A (en) | Phenolic resin composition and method for producing same | |
| JP2020063360A (en) | Adhesive composition for wet friction material | |
| JP7351439B1 (en) | Adhesive composition for wet friction materials and wet friction plates | |
| JP2020172582A (en) | Adhesive composition for wet friction material and wet friction plate | |
| JP2023161359A (en) | Emulsion type phenolic resin composition and adhesive | |
| JP2021031651A (en) | Thermosetting adhesive sheet for friction material and method for manufacturing friction member | |
| WO2023195481A1 (en) | Adhesive composition for wet friction material, and wet friction plate | |
| JP7338809B1 (en) | Phenolic resin composition and articles | |
| WO2021241245A1 (en) | Phenolic resin composition sheet, phenolic resin composition sheet with release film, method for producing b-staged phenolic resin composite sheet, method for producing cured phenolic resin composite sheet, and method for producing carbonized phenolic resin composite sheet | |
| JP2023013156A (en) | Aqueous emulsion resin composition and adhesive | |
| JP2021187942A (en) | Phenolic resin composition sheet, phenolic resin composition sheet with release film, method for producing b-staged phenolic resin composite sheet, method for producing cured phenolic resin composite sheet, and method for producing carbonized phenolic resin composite sheet | |
| JP2021187941A (en) | Resin composition sheet, resin composition sheet with release film, method for producing b-staged resin composite sheet, method for producing cured resin composite sheet, and method for producing carbonized resin composite sheet | |
| JP2021187940A (en) | Phenolic resin composition sheet, phenolic resin composition sheet with release film, method for producing b-staged phenolic resin composite sheet, method for producing cured phenolic resin composite sheet, and method for producing carbonized phenolic resin composite sheet | |
| JP2023153489A (en) | Adhesive composition for wet friction material and wet friction plate | |
| JP2024014036A (en) | Resin compositions, adhesives, and paints | |
| JP2022089312A (en) | Phenol resin composition | |
| JP5035301B2 (en) | Plywood adhesive, production method and use of resol type phenolic resin for plywood adhesive | |
| JP2022029218A (en) | Thermosetting adhesive film, method for producing grinding wheel, and grinding wheel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |