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WO2008016057A1 - Composition de résine durcissable - Google Patents

Composition de résine durcissable Download PDF

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Publication number
WO2008016057A1
WO2008016057A1 PCT/JP2007/065011 JP2007065011W WO2008016057A1 WO 2008016057 A1 WO2008016057 A1 WO 2008016057A1 JP 2007065011 W JP2007065011 W JP 2007065011W WO 2008016057 A1 WO2008016057 A1 WO 2008016057A1
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WO
WIPO (PCT)
Prior art keywords
curable resin
resin composition
compound
group
component
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.)
Ceased
Application number
PCT/JP2007/065011
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English (en)
Japanese (ja)
Inventor
Manabu Kirino
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.)
ThreeBond Co Ltd
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ThreeBond Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ThreeBond Co Ltd filed Critical ThreeBond Co Ltd
Publication of WO2008016057A1 publication Critical patent/WO2008016057A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/30—Nitriles
    • C08F222/32—Alpha-cyano-acrylic acid; Esters thereof
    • C08F222/322—Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate

Definitions

  • the present invention relates to a curable resin containing ⁇ -cyanacrylate as a main component, which is rapidly polymerized and cured by the humidity of the surface of an adherend and / or by irradiation with an energy line such as ultraviolet rays.
  • the present invention relates to a composition, and in particular, can be widely applied to lithography, potting, molding, coating, adhesive, sealant, and various resist materials.
  • the a-cyanoacrylate adhesive rapidly cures anion by a small amount of moisture adsorbed on the adherend surface, and adheres adherends very firmly in a short time. Therefore, it is widely used for bonding metals, plastics, rubber, wood, etc. as a one-component room temperature curing type instant adhesive.
  • the ⁇ -cyanacrylate adhesive is hardened when the distance between adherends is wide, or when it sticks out from the bonded part or is not sandwiched between a pair of adherends like a coating. Has the disadvantage of becoming extremely slow.
  • Patent Literature 1 Patent Literature 2, and Patent Literature 3
  • Odor is undesirable in the working environment. Therefore, it does not impair the excellent features of instant adhesives, which are one-pack type, room temperature rapid curing, and it can be cured easily without using a primer or curing accelerator even if it fills the protruding part or large gap.
  • An ⁇ -cyanacrylate adhesive that can be used is desired.
  • Patent Document 4 and Patent Document 5 describe that a meta-cathecene compound alone, or a meta-cathecene compound and a cleavage type photoradical generator as an ⁇ -cyanacrylate adhesive.
  • a photocurable ⁇ -cyanacrylate composition which is added and contained. This composition can be applied to light in addition to normal moisture curing by moisture on the surface of an adherend. Curing by shooting is possible.
  • Patent Document 6 describes the addition of an aromatic azide compound to a-cyanoacrylate
  • Non-Patent Document 1 describes a technique using Pt (acac) as a photoion polymerization initiator! / The report has been made.
  • Patent Document 7 carboxylic acid ammonium salts
  • Patent Document 8 aminoacetophenone derivatives
  • Patent Document 9 aromatic aminimide compounds
  • Patent Document 10 A combination with a triplet sensitizer, that is, a combination with a hydrogen abstraction type radical generator (Patent Document 10) has been reported.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 59-215376
  • Patent Document 2 JP-A-60-203684
  • Patent Document 3 Japanese Patent Application Laid-Open No. 61-176634
  • Patent Document 4 JP-A-9 249708
  • Patent Document 5 Japanese Patent Laid-Open No. 11 166006
  • Patent Document 6 JP-A-6-299122
  • Patent Document 7 Japanese Patent Laid-Open No. 55-22669
  • Patent Document 8 Japanese Patent Laid-Open No. 11 71450
  • Patent Document 9 International Patent Publication WO2002 / 051905
  • Patent Document 10 Japanese Unexamined Patent Publication No. 2003-26772
  • Non-Patent Document 1 Macromolecules (28 (4) 1328 (1995))
  • Patent Documents 7 to 10 describe compounds that generate bases upon irradiation of light! /, But these compounds are subject to curing reactions! /
  • the polymerizable compound is mainly an epoxy resin and is not intended for an ⁇ -cyanacrylate composition.
  • the object of the present invention is to solve the above-mentioned problems, that is, while maintaining the moisture curability and other physical properties required for an ⁇ -cyanacrylate composition, active energy rays such as ultraviolet rays.
  • An object of the present invention is to provide a curable resin composition that can be cured rapidly by irradiation of the resin and that can be rapidly polymerized and cured by irradiation of moisture or active energy rays.
  • R1 represents an aryl group which may have a functional group.
  • R2, R3 represents an aryl group which may have a functional group.
  • R4 each independently represents an alkyl group which may have a functional group or Z and aryl group.
  • the curable resin composition containing the components (A) and (B) of the present invention as a main component has a conventional moisture-hardening property and can be easily overlapped by irradiation with active energy rays such as ultraviolet rays. Harden. Therefore, the weakness of the moisture-curing ⁇ -cyanacrylate-based composition, poor thick-film curability when used in large quantities and a decrease in curing speed! This can be solved.
  • the curable resin composition comprising the above (ii) and (ii) as a main component becomes a colorless and transparent liquid composition and can be used for applications other than adhesives, such as coating agents and paints. is there.
  • the active energy linear curability is further improved. Therefore, since the amount of component (B) that affects the storage stability of component (A) can be reduced by the combined use of component (C), the storage stability is high V and the curable resin composition. Can be obtained.
  • R is an ester residue such as an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, etc.
  • the number of carbon atoms of the ester residue is not particularly limited, but usually 1 to Those having 8 carbons are also used, and ester residues consisting of alkoxyalkyl groups, trialkylsilylalkyl groups, and substituted hydrocarbon groups can also be used.
  • alkenyl and cycloalkenyl such as alkyl ⁇ -cyanoacrylate, allyl ⁇ -cyanoacrylate, methallyl ⁇ -cyanoacrylate, cyclohexenyl ⁇ -cyanoacrylate, ⁇ -cyanoacrylate, propanegyl ⁇ -cyanoacrylate, etc.
  • / or ⁇ -aminoacetophenone compounds rapidly become one or more basic substances or basic substances by changing the molecular structure or cleaving within the molecule by irradiation with active energy rays. It is a compound that generates a similar substance (photobase generator).
  • examples of the amine imide compound having one or more structures represented by the general formula (I) in the molecule include compounds represented by the general formula (I).
  • R 1 represents an aryl group which may have a functional group.
  • R 2, R 3 and R 4 each independently represents an alkyl group or a da and aryl group which may have a functional group.
  • a known method can be used as a method for synthesizing this amine imide compound.
  • this amine imide compound For example, as described in Encyclopedia of Polymer Science and Engineering, John Ailey & Sons Ltd., (1985), Volume 1, p740, the corresponding carboxylate ester with hydrazine halide and sodium alkoxide. It can be obtained from reaction or reaction of carboxylic acid ester with hydrazine and epoxy compound.
  • the method for synthesizing the aminimide used in the present invention is not particularly limited! /, But considering the simplicity and safety of synthesis, a synthesis method from a carboxylic acid ester, hydrazine and an epoxy compound is preferable. .
  • the synthesis temperature and time are not particularly limited, but in general, the desired aminimide compound can be obtained by stirring at a temperature of 0 to 100 ° C for 30 minutes to 7 days.
  • the carboxylic acid ester as a raw material of the aminimide compound of the present invention used in the case of this synthesis method is a monofunctional or polyfunctional force having a Ri COO structure in the molecule.
  • Any rubonate compound! R1 has a functional group! /, May be! /, And an aryl group.
  • aryl groups include, but are not limited to, phenyl, naphthyl, diphenyl, triphenyl, fluorene, and anthracene groups.
  • Examples of the functional group that R1 may have include alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, carbon atoms;!
  • alkylcarbonyls Group aldehyde group, cyano group, trifluoromethyl group, cyano group, nitro group, phenyl group, benzoyl group, benzyl group, phenyl group substituted with electron donating group and / or electron withdrawing group, or electron donating group
  • Base / Or an electron-withdrawing group is a benzyl group or the like substitution.
  • 4-12 tropenyl groups are preferred from the viewpoint of the balance between stability and curability of the composition, even though substituted phenyl groups are preferred as R1 because of the availability of raw materials.
  • Examples of the carboxylic acid ester compound having 4 12 tropenyl group include methyl 4 12 trobenzoate and ethyl 12 12 trobenzoate.
  • a polyfunctional carboxylic acid ester compound is used, an aminimide compound having a plurality of aminimide structures in the molecule can be obtained.
  • the hydrazine compound is not particularly limited! However, 1,1-dimethylhydrazine is preferred from the standpoint of availability of raw materials and the high basicity of the generated photobasic substance.
  • the epoxy compound as another raw material may be a compound having one or more epoxy groups in the molecule.
  • polyfunctional epoxy compounds such as propylene oxide, glycylol, allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl daricidyl ether, and tertiary butyl phenol glycidyl ether, resorcinol diglycidyl ether, neopentyl diester
  • bis-type liquid epoxy resins such as glycidyl ether, glycerol polyglycidyl ether, diglycidyl ether derived from bisphenol A and epichlorohydrin, derived from aliphatic 'aromatic alcohol and epichlorohydrin
  • Polyfunctional epoxy compounds such as polyglycidyl ethers derived from diyl esters, hydrogenated bisphenol A and epichlorohydrin can also be used
  • the alkyl group represented by R2, R3 and R4 in the general formula (I) is more preferably a methyl group, preferably an alkyl group having!
  • the ⁇ -aminoacetophenone compound which is another compound that can constitute component (B), is a compound having an ⁇ -aminoacetophenone skeleton in the molecule.
  • Specific examples of compounds having an a-aminoacetophenone skeleton include (4 morpholinobenzoyl) 1 Benjirou 1 —dimethylaminopropane (Irgacure 369, trade name of Ciba Specialty Chemicals) and 4 ( A commercially available compound such as methylthiobenzoyl) 1-methyl-1 morpholinoethane (Irgacure 907, trade name of Ciba Specialty Chemicals) or a solution thereof can be used.
  • aminimide compound or ⁇ -aminoacetophenone compound of component (B) at least one of these compounds may be used, but a plurality of these compounds may be used in combination.
  • the blending amount of the component ( ⁇ ⁇ ⁇ ⁇ ) in the curable resin composition of the present invention is not particularly limited, but preferably 0.001 to 100 parts by weight of the total of the component ( ⁇ ). ⁇ ; It is desirable to add in the range of 10 parts by weight.
  • the component ( ⁇ ) is added within the above range, it is possible to obtain a curable composition having an excellent balance between the curing speed and the strength of the cured product, storage stability, and the like. If the amount is less than 001 parts by weight, the curable composition of the present invention cannot be provided with effective photocurability, and if it exceeds 10 parts by weight, it is difficult to dissolve in the component (v), and storage stability and various physical properties are also provided. May be adversely affected.
  • the composition comprising the above components (i) and (ii) as the main component is further added to (C) an active energy linear radical generator (however, as the component (C) of the present invention, Addition of (ii) excluding ⁇ -aminoacetophenone compound used as a component can further enhance the photoactivity of the composition.
  • This active energy ray radical generator is a compound that generates radical species upon irradiation with active energy rays such as ultraviolet rays, and is a hydrogen abstraction type radical generator.
  • the force S that is broadly divided into intramolecular cleavage type radical generators, and the force S that can be used without distinction in the present invention.
  • hydrogen abstraction-type radical canore generators examples include 1-methylnaphthalene, 2-methylnaphthalene, 1-funole ronaftalene, 1 chloronaphthalene, 2-chloronaphthalene, 1 'mouth monaphthalene, 2' mouth monaphthalene, 1-odonaphthalene, 2--naphthonaphthalene, 1-naphthol, 2-naphthol, 1-methoxynaphthalene, 2-methoxynaphthalene, 1, 4--naphthalene derivatives such as dicyanonaphthalene, anthracene, 1,2-benzanthracene, 9, Anthracene derivatives such as 10 diclonal anthracene, 9, 10 dibromoanthracene, 9, 10 diphenylanthracene, 9 cyananoanthracene, 9,10 dicyananthracene, 2, 6, 9, 10 tetracyananthracene, pyrene
  • the intramolecular cleavage type radical generator is a type of radical generator that generates radicals by cleavage of the compound when irradiated with active energy rays.
  • Specific examples thereof include benzoin ether derivatives, (Excluding ⁇ -aminoacetophenone compound)
  • Arylphene ketones such as acetphenone derivatives, oxime ketones, acyl phosphine oxides, thiobenzoic acid S phenyls, titanocenes, and high molecular weights thereof Derivatives, but not limited to these.
  • cleavable radical generators include 1- (4-dedecylpenzoyl) -1-hydroxy-1-monomethylethane, 1-1- (4-isopropylbenzol) 1-hydroxy-1-methylethane, 1 1-hydroxy-1- 1-methylethane, 1- [4- (2 hydroxyethoxy) monobenzoyl 1-hydroxy 1-methylethane, 1 [4 (ataryloxyethoxy) monobenzoyl] -1- 1-hydroxy 1-methylethane, diphenylketone, phenylolene 1-hydroxycyclohexenoleketone, penzinoresimethinoreketanol, bis (cyclopentageninole) -bis (2, 6 difluoro-1-pyryl-1-phenyl) titanium, (7 ] 6 —Isopropylbenzene) 1 (7) 5 —Cyclopentaenyl) Iron ( ⁇ ) hexafluorophosphate, trim Tinole Benzyldiphenylphos
  • these (C) active energy ray radical generators that is, hydrogen abstraction type or cleavage type radical generators can be used alone. You can use a combination of multiple forces, but the stability of the radical generator alone In view of the properties and curability of the composition in the present invention, a combination of two or more containing at least one cleavage type radical generator is preferred. Also, high molecular weight type with the structure of high molecular oligomer / cleavable radical generator in the polymer is preferred because of less outgassing during and after curing!
  • component (B) and component (C) You can choose the best combination of! / , depending on the type of (C) active energy ray radical generator, there may be a difference in the effect depending on the structure and type of component (B) to be combined with this, so component (B) and component (C) You can choose the best combination of! / ,.
  • the addition amount of the (C) active energy ray radical generator in the curable resin composition of the present invention needs to refer to the absorption wavelength and the molar extinction coefficient, but generally the curable resin composition of the present invention.
  • Component (A) is 100 parts by weight, 0.00;! To 50 parts by weight, preferably 0.01 to 10 parts by weight. If the amount added is small, a sufficient photoactivity improving effect cannot be obtained, and if it is too large, the basic catalytic action of component (B) may be inhibited.
  • additives can be used in combination with the cured composition of the present invention as long as the characteristics of the present invention are not impaired.
  • a radical polymerizable compound such as an acrylate ester
  • anionic polymerization inhibitors such as an acrylate ester
  • radical polymerization inhibitors thickeners, curing accelerators, plasticizers, tougheners, fragrances, dyes
  • Specific additives such as pigments, fillers, and heat stabilizers can be added as necessary.
  • Anionic polymerization inhibitors are added to increase stability during storage of the composition. Examples of known inhibitors include sulfur dioxide, sulfur trioxide, nitric oxide, hydrogen fluoride and p-toluenesulfonic acid, etc., generally in the range of 0.;! To lOOOOppm relative to ⁇ -cyanate acrylate. It is accompanied.
  • radical polymerization inhibitors examples include quinone, hydroquinone, t-butylcatechol, and p-methoxyl phenol, and are generally added in the range of 0.1 to 1000 Oppm with respect to ⁇ -cyanacrylate. .
  • thickeners are added to increase the viscosity of the composition.
  • thickeners include poly (methyl) metatalylate, metatalylate type copolymers, acrylic rubber, cellulose derivatives, polybutyrate and poly ( ⁇ -cyanacrylate).
  • many conventional polymer additives are also added for toughening. Examples thereof include an acrylic elastomer, an acrylonitrile copolymer elastomer, a fluoroelastomer and a fine silica filler. These substances also function as thickeners.
  • the curable resin composition of the present invention has a long life at room temperature and has a pot life, and in addition to rapid polymerization and curing due to moisture in the atmosphere or the surface of the adherend, it also exhibits active energy rays such as light. Even when irradiated, it cures quickly, forming a tough cured product and developing strong adhesion to metals and plastics.
  • a one-component curable resin composition in which a composition containing component (A) a-cyanoacrylate and a photobase generator as component (B) are mixed can be used, and component (A) and (B) may be separated into two-component compositions and polymerized and cured by a method of mixing or contacting immediately before use.
  • a form is arbitrarily selected depending on the types of the components (A) to (C), particularly the combination of the components (B) and (C).
  • aminimide compounds used in Examples and Comparative Examples are compounds represented by the structural formulas shown in Table 1, and those synthesized by the following methods were used.
  • Aminimides a and are amine imides of the present invention
  • aminimides c to h are aminimide compounds that are not included in the amine imide compounds of the present invention.
  • each raw material excluding ethyl cyanoacrylate is stirred and dissolved in acetone in a light-shielding container. This acetone solution was dropped into ethyl acetate and dissolved in a light-shielding container to obtain each composition. Next, each test described below was performed on each of the obtained compositions, and the results are also shown in Table 2.
  • each composition 0.5 g is dropped into a plastic cup with an inner diameter of 24 mm and irradiated with active energy rays using a spot ultraviolet irradiation device (365 nm illuminance: 100 mW / cm 2 ) manufactured by Hamamatsu Photonics Co. From this, the integrated light quantity was obtained. Those that reacted vigorously immediately after mixing and gelled were marked as impossible to measure in the table.
  • a spot ultraviolet irradiation device 365 nm illuminance: 100 mW / cm 2
  • Examples 13 to 15 show that the storage stability can be improved while maintaining sufficient photocurability by adding an organic acid derivative. Further, Example 15 shows that the amine imide compound b of the present invention having a structure other than the amine imide compound a is also effective. In Example 16, it can be seen that there is no adverse effect even if a filler is added.
  • Examples 17 to 18 show that when the ⁇ -aminoacetophenone compound of the present invention is used, it has a long pot life and is instantly cured by light. From Example 19, it can be seen that photocurability is improved by adding an arbitrary radical generator. From Examples 20 and 21, it can be seen that the amine imide compound of the present invention and the a-aminoacetophenone compound can be used in combination, and the photocurability is further improved by adding a radical generator.
  • Comparative Examples 6 and 7 are aliphatic aminimides not included in the present invention, and a compound having a substituent having a very strong electron-withdrawing property to carbonyl carbon has a long pot life, but has a photoactivity. It can be seen that low enough photocurability cannot be obtained. This may be because the basicity before light irradiation is sufficiently low, but the photoactivity is also low.
  • spot ultraviolet irradiation device (365nm illuminance: 10) manufactured by Hamamatsu Photonicus OmW / cm 2 )
  • active energy rays are irradiated for 10 seconds (lj / cm 2 )
  • the time until the adhesive interface hardens and does not move immediately after bonding
  • the time until the whole is cured the whitening phenomenon around the protruding part (a phenomenon in which the uncured ⁇ -cyanacrylate compound hardens and drops due to moisture in the air after volatilization and adheres as a white cured product to the periphery)
  • the presence or absence was confirmed.
  • the curable resin composition of the present invention can be used for a known application in which an ⁇ -cyanacrylate-based adhesive is conventionally used, that is, an adhesive utilizing moisture curability. Because it cures and cures quickly even when irradiated with energy rays such as ultraviolet rays, It can also be used for adhesive bonding and coating applications, paints, paints, and various resist materials.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne une composition de résine durcissable qui peut être durcie rapidement par irradiation avec un rayonnement d'énergie active tel qu'une lumière ultraviolette, tout en conservant une aptitude au durcissement à l'humidité et diverses autres propriétés requises pour des compositions de α-cyanoacrylate. Ladite composition de résine durcissable peut être durcie rapidement à la fois par l'humidité et par irradiation avec un rayonnement d'énergie active. L'invention concerne spécifiquement une composition de résine durcissable contenant (A) un α-cyanoacrylate et (B) un composé d'amine imide ayant une ou plusieurs structures représentées par la formule générale (I) ci-dessous dans une molécule et/ou un composé de α-aminoacétophénone. [formule chimique 1] formule générale (I) (Dans la formule, R1 représente un groupe aryle qui peut avoir un groupe fonctionnel ; et R2, R3 et R4 représentent indépendamment un groupe aryle et/ou un groupe alkyle qui peuvent avoir un groupe fonctionnel.)
PCT/JP2007/065011 2006-08-02 2007-07-31 Composition de résine durcissable Ceased WO2008016057A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-210519 2006-08-02
JP2006210519A JP2008037907A (ja) 2006-08-02 2006-08-02 硬化性樹脂組成物

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WO2008016057A1 true WO2008016057A1 (fr) 2008-02-07

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JP (1) JP2008037907A (fr)
TW (1) TW200813100A (fr)
WO (1) WO2008016057A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010147161A1 (fr) * 2009-06-17 2010-12-23 株式会社スリーボンド Générateur de base et de radicaux, composition l'utilisant et procédé pour son durcissement
WO2021059189A1 (fr) * 2019-09-27 2021-04-01 3M Innovative Properties Company Procédé de moulage et compositions associées

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JP2012082248A (ja) * 2010-10-07 2012-04-26 Autonetworks Technologies Ltd 湿気硬化性液状組成物およびこれを用いた硬化物
JP5700203B2 (ja) * 2010-12-22 2015-04-15 スリーボンドファインケミカル株式会社 アミンイミド化合物、およびそれを用いた組成物およびその硬化方法
JP5637214B2 (ja) * 2011-06-16 2014-12-10 三菱レイヨン株式会社 中空糸膜モジュールの補修方法および中空糸膜モジュール
JP2020200403A (ja) * 2019-06-11 2020-12-17 学校法人東京理科大学 活性エネルギー線硬化型組成物

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JP2005015584A (ja) * 2003-06-25 2005-01-20 Jsr Corp 感放射線性屈折率変化性組成物、パターン形成法および光学材料
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JPS6257475A (ja) * 1985-09-06 1987-03-13 Toagosei Chem Ind Co Ltd 接着剤
JPH06299122A (ja) * 1993-04-16 1994-10-25 Three Bond Co Ltd 接着剤組成物
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JP2003246930A (ja) * 2002-02-25 2003-09-05 Jsr Corp 感放射線性屈折率変化性組成物および屈折率変化法
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Publication number Priority date Publication date Assignee Title
WO2010147161A1 (fr) * 2009-06-17 2010-12-23 株式会社スリーボンド Générateur de base et de radicaux, composition l'utilisant et procédé pour son durcissement
EP2444391A4 (fr) * 2009-06-17 2012-11-14 Three Bond Co Ltd Générateur de base et de radicaux, composition l'utilisant et procédé pour son durcissement
CN102803205A (zh) * 2009-06-17 2012-11-28 三键株式会社 碱和自由基产生剂、使用其的组合物及固化所述组合物的方法
US8686059B2 (en) 2009-06-17 2014-04-01 Three Bond Co., Ltd. Base and radical generator, composition using same and method for curing same
JP5549819B2 (ja) * 2009-06-17 2014-07-16 スリーボンドファインケミカル株式会社 塩基およびラジカル発生剤、およびそれを用いた組成物およびその硬化方法
CN102803205B (zh) * 2009-06-17 2015-12-16 三键精密化学有限公司 碱和自由基产生剂、使用其的组合物及固化所述组合物的方法
WO2021059189A1 (fr) * 2019-09-27 2021-04-01 3M Innovative Properties Company Procédé de moulage et compositions associées
US11993004B2 (en) 2019-09-27 2024-05-28 3M Innovative Properties Company Molding process and compositions therefor

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JP2008037907A (ja) 2008-02-21

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