WO2023224054A1 - 樹脂組成物、硬化物、積層体及び積層体の製造方法 - Google Patents

樹脂組成物、硬化物、積層体及び積層体の製造方法 Download PDF

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Publication number
WO2023224054A1
WO2023224054A1 PCT/JP2023/018356 JP2023018356W WO2023224054A1 WO 2023224054 A1 WO2023224054 A1 WO 2023224054A1 JP 2023018356 W JP2023018356 W JP 2023018356W WO 2023224054 A1 WO2023224054 A1 WO 2023224054A1
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Prior art keywords
group
resin composition
laminate
dicyanoethylene
carbon atoms
Prior art date
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Ceased
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PCT/JP2023/018356
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English (en)
French (fr)
Japanese (ja)
Inventor
敦 稲富
淳裕 中原
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kuraray Co Ltd
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Kuraray Co Ltd
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Filing date
Publication date
Application filed by Kuraray Co Ltd filed Critical Kuraray Co Ltd
Priority to EP23807655.8A priority Critical patent/EP4527864A1/en
Priority to US18/867,216 priority patent/US20250304735A1/en
Priority to CN202380040724.6A priority patent/CN119137171A/zh
Priority to KR1020247038067A priority patent/KR20250009982A/ko
Priority to JP2024521955A priority patent/JPWO2023224054A1/ja
Publication of WO2023224054A1 publication Critical patent/WO2023224054A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/732—Dimensional properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages

Definitions

  • the present invention relates to a resin composition, a cured product, a laminate, and a method for producing a laminate, including a 1,1-dicyanoethylene and a specific polymerizable monomer.
  • 2-cyanoacrylic acid alkyl esters which undergo anionic polymerization even in weak Lewis basic compounds such as water and alcohol, are used as the main raw material.
  • it is required to have heat resistance and moisture resistance in addition to adhesive strength.
  • heat resistance and moisture resistance can be improved by adding various additives.
  • Adhesives have been proposed.
  • Patent Document 1 and Patent Document 2 have improved heat resistance and moisture resistance compared to conventional adhesives, they are not sufficient, so further improvements are required.
  • the present inventors conducted a study and found that highly reactive 2-cyanoacrylic acid alkyl ester has a property that it is difficult to copolymerize with other monomers, but it is easy to copolymerize with 1,1-dicyanoethylene. I found out. Further studies based on this knowledge revealed that a cured product obtained from a resin composition containing 1,1-dicyanoethylene and a polymerizable monomer with a specific structure in a specific ratio showed adhesive properties. They discovered that they not only have excellent heat resistance and moisture resistance, but also completed the present invention.
  • the content of the 1,1-dicyanoethylene (A) is 2.0 to 99.9% by mass in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B).
  • R 3 is a carboxyl group, an ester group represented by -COOR 5 (R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more), and an acid anhydride.
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or
  • the polymerizable monomer (B) is one or more selected from 2-cyanoacrylic acid alkyl ester, 2-cyanopentadienoic acid alkyl ester, and methylidene malonic acid dialkyl ester.
  • the resin composition described in . [3] The resin composition according to [1] or [2] above, further comprising a Br ⁇ nsted acidic compound.
  • [4] A cured product obtained by curing the resin composition according to any one of [1] to [3] above with a Lewis basic compound.
  • a method for producing a laminate comprising an adhesion step of adhering a first adherend and a second adherend with the resin composition according to any one of [1] to [3] above.
  • the present invention it is possible to provide a resin composition that can provide an adhesive with excellent heat resistance and moisture resistance, and a cured product using the same. Furthermore, a laminate using the cured product and a method for manufacturing the laminate can be provided.
  • the resin composition of the present invention is a resin composition containing 1,1-dicyanoethylene (A) and a polymerizable monomer (B) represented by the following general formula (I),
  • the content of the 1,1-dicyanoethylene (A) is 2.0 to 99.9% by mass in the total of the 1,1-dicyanoethylene (A) and the polymerizable monomer (B). It is characterized by certain things.
  • R 1 is one or more selected from a hydrogen atom, an alkyl group, an alkenyl group, and an alkoxy group
  • R 2 is selected from a cyano group, a carboxy group, an ester group represented by -COOR 4 (R 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms), and an acid anhydride group.
  • R 3 is a carboxyl group, an ester group represented by -COOR 5 (R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more), and an acid anhydride.
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or
  • 1,1-dicyanoethylene (A) is preferred as a raw material for fast-curing adhesives due to its excellent reactivity, and when used in combination with the polymerizable monomer (B) described below, it improves heat resistance and moisture resistance.
  • An excellent resin composition for adhesives can be obtained.
  • 1,1-dicyanoethylene can be obtained by the production method described in J.Am.Chem.Soc., 1989, 111, 9078-9081 and US2476270.
  • the polymerizable monomer (B) is a monomer represented by the following general formula (I).
  • CHR 1 CR 2 R 3 (I)
  • R 1 is one or more selected from a hydrogen atom, an alkyl group, an alkenyl group, and an alkoxy group.
  • the alkyl group for R 1 is preferably an alkyl group having 1 to 12 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group. group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, and the like.
  • the alkenyl group for R 1 is preferably an alkenyl group having 2 to 12 carbon atoms, such as a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a pentenyl group, a prenyl group, Examples include hexenyl group (cis-3-hexenyl group, etc.), cyclohexenyl group, and the like.
  • the alkoxy group for R 1 is preferably an alkoxy group having 1 to 10 carbon atoms, such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group. group, and tert-butoxy group.
  • R 1 is preferably a hydrogen atom, an alkyl group, or an alkenyl group, and more preferably a hydrogen atom.
  • R 2 is a cyano group, a carboxy group, or an ester group represented by -COOR 4 (R 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms). and an acid anhydride group.
  • R 2 may be an ester group represented by --COOR 4 , and R 4 in this case is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • R 4 in this case is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • the alkyl group having 1 to 10 carbon atoms for R 4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- Examples include pentyl group, isopentyl group, neopentyl group, and n-hexyl group.
  • the aryl group having 6 to 20 carbon atoms for R 4 include phenyl group, tolyl group, xylyl group, and naphthyl group.
  • R 2 may be an acid anhydride group, such as phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylnadic anhydride, nadic anhydride
  • acid anhydride groups derived from acids, glutaric anhydride, dimethylglutaric anhydride, diethylglutaric anhydride, succinic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, and the like.
  • R 2 is preferably a cyano group, a carboxy group, or -COOR 4 (R 4 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms), and is preferably a cyano group. More preferred.
  • R 3 is a carboxyl group, an ester group represented by -COOR 5 (R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a linking group with a valence of 2 or more), and an acid anhydride.
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or more linking group.
  • Examples of the alkyl group having 1 to 10 carbon atoms for R 5 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- Examples include pentyl group, isopentyl group, neopentyl group, and n-hexyl group.
  • Examples of the aryl group having 6 to 20 carbon atoms for R 5 include phenyl group, tolyl group, xylyl group, and naphthyl group.
  • Examples of the divalent or higher-valent linking group for R 5 include linking groups derived from divalent or higher-valent alcohols such as ethylene glycol and glycerin.
  • Specific examples of compounds where R 5 is a divalent or higher linking group include compounds obtained by esterification reaction of ethylene glycol and two 2-cyanoacrylic acids (so-called “bifunctional cyanoacrylates”); Examples include compounds obtained by esterification reaction of glycerin and three 2-cyanoacrylic acids (so-called "trifunctional cyanoacrylates”).
  • Examples of the compound constituting the linking group include ethylene glycol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, Examples include diols such as 1,9-nonanediol, 1,10-decanediol, and 1,12-dodecanediol, and trihydric or higher polyhydric alcohols such as glycerin, pentaerythritol, trimethylolpropane, and sorbitol. It will be done.
  • the divalent or higher-valent linking group is preferably a di- to trivalent linking group.
  • R 3 may be an acid anhydride group, such as phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylnadic anhydride, nadic anhydride
  • acid anhydride groups derived from acids, glutaric anhydride, dimethylglutaric anhydride, diethylglutaric anhydride, succinic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, and the like.
  • R 3 is a carboxy group, -COOR 5 (R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or more linking group).
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or more linking group.
  • An ester group represented by is preferable, and an ester group represented by -COOR 5 (R 5 in this case is an alkyl group having 1 to 6 carbon atoms or a divalent to trivalent linking group) is more preferable.
  • R 5 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a divalent or more linking group.
  • the polymerizable monomer (B) includes 2-cyanoacrylic acid alkyl ester, 2-cyanopentadienoic acid alkyl ester, and methylidenemalone, from the viewpoint of improving adhesive strength when the resin composition is used as an adhesive.
  • One or more types selected from acid dialkyl esters are preferred, and ethyl 2-cyanoacrylate is more preferred.
  • the method for producing the polymerizable monomer (B) is not particularly limited, and known methods can be used alone or in combination. Furthermore, the polymerizable monomer (B) may be a commercially available product, such as ethyl 2-cyanoacrylate (manufactured by Aldrich).
  • the content of the 1,1-dicyanoethylene (A) is 2.0 to 99% in the total of 1,1-dicyanoethylene (A) and the polymerizable monomer (B). .9% by mass.
  • the content of 1,1-dicyanoethylene (A) is at least the above lower limit, the heat resistance and moisture resistance of the cured product obtained from the resin composition will improve.
  • the content of 1,1-dicyanoethylene (A) is below the above-mentioned upper limit, the rapid curing properties of the resin composition are improved.
  • the content of the 1,1-dicyanoethylene (A) is 7.0 to 99.9 mass in the total of 1,1-dicyanoethylene (A) and the polymerizable monomer (B). %, more preferably 30.0 to 99.9% by mass, even more preferably 50.0 to 99.9% by mass, and even more preferably 70.0 to 99.9% by mass. It is even more preferable.
  • the content of the polymerizable monomer (B) is 0.1 to 93.0% by mass in the total of 1,1-dicyanoethylene (A) and the polymerizable monomer (B). It is preferably from 0.1 to 70.0% by mass, even more preferably from 0.1 to 50.0% by mass, and even more preferably from 0.1 to 30.0% by mass. More preferred.
  • the total content of 1,1-dicyanoethylene (A) and polymerizable monomer (B) in the resin composition of the present invention is not particularly limited, it is preferably 80% by mass or more, and 90% by mass. % or more, more preferably 95% by mass or more, even more preferably substantially 100% by mass.
  • the resin composition of the present invention further contains a Bronsted acidic compound.
  • the resin composition of the present invention contains a Br ⁇ nsted acidic compound
  • the reactivity of 1,1-dicyanoethylene (A) can be controlled and storage stability is improved. More specifically, since 1,1-dicyanoethylene (A) hardens with a small amount of moisture, it is preferable to completely remove moisture during the manufacturing process, but it is not realistic to completely remove moisture. Since this is difficult, it is preferable to suppress curing (suppress initiation of polymerization) by protonating water using a Br ⁇ nsted acidic compound.
  • Examples of the Br ⁇ nsted acidic compound that can be used in the present invention include inorganic acids, carboxylic acids, and organic sulfonic acids from the viewpoint of improving reactivity and easy availability.
  • sulfuric acid, hydrochloric acid, nitric acid, etc. acetic acid, benzenesulfonic acid, p-toluenesulfonic acid, and methanesulfonic acid, and a compound exhibiting Bronsted acidity by reacting with water, such as sulfur dioxide and diphosphorus pentoxide. It may also be a compound that produces
  • the content thereof is preferably 0.0001 to 2.0% by mass, and 0.001 to 1.0% by mass in the total amount of the resin composition.
  • the content is more preferably 0.001 to 0.05% by mass, and even more preferably 0.001 to 0.05% by mass.
  • the content of the 1,1-dicyanoethylene (A) in the total amount of the resin composition is preferably 80% by mass or less, more preferably 50% by mass or less, and 30% by mass. % or less, and even more preferably 10% by mass or less.
  • the resin composition of the present invention may further contain other components such as a solvent, a filler, a thickener, an anti-aging agent, a plasticizer, a flame retardant, a stabilizer, and an antioxidant.
  • the content thereof is preferably 0.001% by mass or more, and preferably 10% by mass or less, and 3% by mass in the total amount of the resin composition. % or less is more preferable.
  • ⁇ Method for manufacturing resin composition> There are no particular limitations on the method for producing the resin composition of the present invention, and for example, a mixing step of mixing 1,1-dicyanoethylene (A), the polymerizable monomer (B), and other components as necessary. However, if mixed in air, the polymerization reaction will proceed due to moisture in the air, so it is preferable to manufacture in a dry atmosphere. Note that there is no particular restriction on the method of mixing each component, and any known method can be used.
  • the cured product of the present invention is obtained by curing the resin composition of the present invention described above with a Lewis basic compound. More specifically, the cured product is obtained by curing each component in the resin composition using a Lewis basic compound as a catalyst. It is a copolymer.
  • the Lewis basic compound used in the present invention is not particularly limited, but for example, one or more selected from water, alcohol, and alkylamine can be used, and alcohols include methanol, ethanol, propanol, and the like.
  • alcohols include methanol, ethanol, propanol, and the like.
  • alkylamine include tertiary amines such as trimethylamine, triethylamine, tripropylamine, triisopropylamine, N,N-dimethylethylamine, N,N-dimethylpropylamine, and N,N-dimethylisopropylamine.
  • Method for producing cured product There is no particular restriction on the method for producing the cured product, and it can be obtained by mixing the resin composition of the present invention and a Lewis basic compound at room temperature (23°C), but generally the resin composition of the present invention A cured product can be obtained by reacting the material with moisture in the air (Lewis basic compound).
  • the amount of the Lewis basic compound is not particularly limited, but it is preferably 0.001 to 1.0 parts by weight, and 0.01 to 0.5 parts by weight based on 100 parts by weight of the resin composition. is even more preferable. When the content of the Lewis basic compound is within the above range, the resin composition reacts quickly.
  • the laminate of the present invention is a laminate having a layer containing the cured product, and although there is no particular restriction on the laminated structure, it is preferable to have the cured product between two adherends. By having the cured product between two objects to be adhered, it is possible to firmly adhere the objects to be adhered to each other.
  • Examples of synthetic resins include polyethylene, polypropylene, copolymers of ethylene and one or more ⁇ -olefins having 3 to 20 carbon atoms (for example, propylene, 1-butene, 1-pentene, 1-hexene, etc.), and ethylene-propylene.
  • Examples include polyolefin resins such as -diene copolymer (EPDM), ethylene-vinyl acetate copolymer, and ethylene-acrylic acid copolymer, polyurethane resin, polyamide resin, polyester resin, and polycarbonate resin.
  • Examples of the metal include steel plates such as stainless steel plates, cold-rolled steel plates, and alloyed galvanized steel plates.
  • the thickness of the adherend that constitutes the laminate there is no particular limit to the thickness of the adherend that constitutes the laminate.
  • the thickness of the layer containing the cured product is preferably 0.01 to 2.0 mm, more preferably 0.015 to 1.5 mm, from the viewpoint of firmly adhering the objects to be adhered.
  • the thickness is preferably 0.02 to 1.2 mm, and more preferably 0.02 to 1.2 mm.
  • the method for producing a laminate of the present invention includes an adhesion step of bonding a first adherend and a second adherend with the resin composition. It is preferable. There is no particular restriction on the method of bonding the first adhered object and the second adhered object with the resin composition, but for example, one adherend object is coated with the resin composition, and the other adhered object is coated with the resin composition. Bonding can be achieved by overlapping and curing the objects to be bonded.
  • the amount of the resin composition applied to the object to be adhered is preferably 0.01 to 3.0 ⁇ L/mm 2 , more preferably 0.05 to 2.5 ⁇ L/mm 2 . , more preferably 0.1 to 2.0 ⁇ L/mm 2 .
  • the application amount is equal to or greater than the lower limit value, objects to be adhered can be firmly adhered to each other.
  • the coating amount is below the upper limit value, both can be bonded together with an appropriate amount.
  • Example 1 Under dry nitrogen, 0.02 g of 1,1-dicyanoethylene (A) and 0.98 g of ethyl 2-cyanoacrylate (polymerizable monomer (B)) were mixed. Furthermore, a resin composition was prepared by blending a Br ⁇ nsted acidic compound (methanesulfonic acid) into this mixture so that its content was 0.01% by mass in the total amount of the resin composition. This resin composition was evaluated according to JIS K6861:1995. Specifically, 100 ⁇ L of the obtained resin composition was applied to a 12.5 mm x 25 mm area of a steel plate, and another steel plate was placed on this coated surface.
  • a Br ⁇ nsted acidic compound methanesulfonic acid
  • the resin composition is cured by allowing it to stand for one day at room temperature (23°C) and 50% RH to mix water as a Lewis basic compound, thereby bonding the two steel plates together to form a laminate. Obtained.
  • the tensile shear adhesive strength of each laminate was measured under the following conditions. The results are shown in Table 1.
  • ⁇ Standard adhesion test> The tensile shear adhesive strength of the laminate was measured at 25% RH and 25° C. using a universal material testing machine model 5969 (manufactured by Instron) at a tensile speed of 20 mm/min.
  • ⁇ Heat-resistant adhesion test> The laminate was left undisturbed for 3 days at 25% RH and 120°C in a constant temperature and humidity chamber, and then the tensile shear adhesive strength of the laminate was measured at 25% RH and 25°C using a universal material testing machine model 5969 (Instron). The measurement was carried out at a tensile speed of 20 mm/min.
  • ⁇ Moisture resistant adhesion test> The laminate was allowed to stand for one day at 90% RH and 40°C in a constant temperature and humidity chamber, and then the tensile shear adhesive strength of the laminate was measured at 25% RH and 25°C using a universal material testing machine model 5969 (Instron). (manufactured by Co., Ltd.) at a tensile speed of 20 mm/min.
  • Examples 2 to 16 Comparative Examples 1 to 4> A laminate was prepared in the same manner as in Example 1, except that the resin composition was prepared according to the formulations listed in Tables 1 to 3, and the tensile shear adhesive strength was measured in the same manner. The results are shown in Tables 1 to 3.
  • the resin composition of the present invention exhibits excellent heat resistance and moisture resistance when used as an adhesive. Moreover, from the results in Table 4, it can be seen that the resin composition of the present invention also has excellent storage stability.

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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)
  • Engineering & Computer Science (AREA)
  • Toxicology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
PCT/JP2023/018356 2022-05-20 2023-05-16 樹脂組成物、硬化物、積層体及び積層体の製造方法 Ceased WO2023224054A1 (ja)

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WO2024085249A1 (ja) * 2022-10-21 2024-04-25 株式会社クラレ 樹脂組成物、樹脂組成物を用いた成形加工品及びフィルム
WO2025249264A1 (ja) * 2024-05-30 2025-12-04 株式会社クラレ １，１－ジシアノエチレン組成物用容器、及び内容物入り容器

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US2476270A (en) 1947-11-12 1949-07-19 Goodrich Co B F Preparation of 1, 1-dicyano ethylene by the pyrolysis of 1-acetoxy-1, 1-dicyano ethane
US4199359A (en) * 1968-05-16 1980-04-22 Xerox Corporation Photographic screen stencil printing process
JPS63277218A (ja) * 1986-12-29 1988-11-15 Toppan Printing Co Ltd 単分散重合体の製造方法
JP2021059620A (ja) * 2019-10-03 2021-04-15 株式会社リコー 液体組成物セット、収容容器セット、硬化物形成装置、硬化物形成方法、及び液体組成物

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US4199359A (en) * 1968-05-16 1980-04-22 Xerox Corporation Photographic screen stencil printing process
JPS63277218A (ja) * 1986-12-29 1988-11-15 Toppan Printing Co Ltd 単分散重合体の製造方法
JP2021059620A (ja) * 2019-10-03 2021-04-15 株式会社リコー 液体組成物セット、収容容器セット、硬化物形成装置、硬化物形成方法、及び液体組成物

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WO2024085249A1 (ja) * 2022-10-21 2024-04-25 株式会社クラレ 樹脂組成物、樹脂組成物を用いた成形加工品及びフィルム
WO2025249264A1 (ja) * 2024-05-30 2025-12-04 株式会社クラレ １，１－ジシアノエチレン組成物用容器、及び内容物入り容器

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