CN103097436A - Resin composition - Google Patents

Resin composition Download PDF

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Publication number
CN103097436A
CN103097436A CN2012800027535A CN201280002753A CN103097436A CN 103097436 A CN103097436 A CN 103097436A CN 2012800027535 A CN2012800027535 A CN 2012800027535A CN 201280002753 A CN201280002753 A CN 201280002753A CN 103097436 A CN103097436 A CN 103097436A
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resin combination
resin
compound
acrylic resin
radical polymerization
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岩谷一希
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Namics Corp
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Namics Corp
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/14—Polysulfides
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • 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
    • C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • 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
    • C09J147/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Adhesives based on derivatives of such polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
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    • 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
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    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • C09J2433/00—Presence of (meth)acrylic polymer
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0625—Polyacrylic esters or derivatives thereof

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  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Epoxy Resins (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Provided is a light- and heat-curable resin composition that has a sufficiently long pot life. The resin composition contains (A) an acrylic resin, (B) a thiol compound, (C) a latent curing agent, (D) a radical polymerization inhibitor, and (E) an anionic polymerization suppressor. The resin composition preferably further contains (F) a radical polymerization initiator. The resin composition preferably also contains (G) a compound other than an acrylic resin having at least two double bonds.

Description

Resin combination
Technical field
The present invention relates to the resin combination that solidifies by light and heating.More specifically, relating to by rayed can be temporary fixed, can completely crued light and heat curable resin composition by heating.
Background technology
Used in a plurality of fields by ultraviolet ray (UV) and shone and caking agent (for example with reference to patent documentation 1,2) temporary fixed, make its completely crued type by heat, particularly often be utilized in the image sensor module purposes.Image sensor at high temperature a little less than, so caking agent needs curability at low temperatures.On the other hand, from the production cost aspect, caking agent also needs solidified nature in short-term simultaneously.As the example of the caking agent of low-temperature short-time curing, can enumerate thio-alcohol caking agent (for example with reference to patent documentation 3,4).But it is very difficult giving the UV solidified nature to the thio-alcohol caking agent.This is due to following cause: have the acrylic resin of UV solidified nature and reaction and the resin (for example epoxy resin) except acrylic resin of mercaptan resin and Comparatively speaking more easily carry out with the reaction of mercaptan resin, therefore, can foreshorten to the level that to use in practical the storage period of caking agent.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2009-51954 communique
Patent documentation 2: international disclosing No. 2005/052021
Patent documentation 3: Japanese kokai publication hei 6-211969 communique
Patent documentation 4: Japanese kokai publication hei 6-211970 communique
Summary of the invention
Invent problem to be solved
The present invention completes in view of the above problems, and its purpose is, the curable resin composition of the light and heat with sufficiently long storage period is provided.
For the method for dealing with problems
The inventor etc. are in order to solve above-mentioned problem, and various experiments and research have been carried out, new discovery as a result on the basis of acrylic resin, mercaptan resin and latent curing agent, further add radical polymerization stopper and anionoid polymerization inhibitor, can obtain thus having the light and heat curable resin composition with sufficiently long storage period of the level that can tolerate actual use, thereby complete the present invention.
That is, the present invention is a kind of resin combination, and it contains (A) acrylic resin, (B) mercaptan compound, (C) latent curing agent, (D) radical polymerization stopper and (E) anionoid polymerization inhibitor.
Resin combination of the present invention preferably also contains (F) radical polymerization initiator.
Resin combination of the present invention preferably also contains the compound except acrylic resin that (G) has the two keys more than two.
(G) compound except acrylic resin that has two keys more than two is preferably and is selected from polyhutadiene, polyvingl ether, have the polyhutadiene of the glycidyl more than two and have at least a in the polyvingl ether of the glycidyl more than two.
(A) acrylic resin/(B) the mercaptan compound equivalence ratio is preferably 0.5～2.0.
(D) content of radical polymerization stopper is preferably 0.0001～1.0wt% for the resin combination total amount.
(E) content of anionoid polymerization inhibitor preferably counts 0.001～1.0 with weight ratio for the content of (C) latent curing agent.
(D) the radical polymerization stopper is preferably and is selected from least a in N-nitroso-group-N-Phenylhydroxylamine aluminium, triphenylphosphine, p methoxy phenol and Resorcinol.
(E) the anionoid polymerization inhibitor is preferably and is selected from least a in boric acid ester, aluminium chelate and organic acid.
In addition, the invention provides caking agent or the sealing agent that contains the described resin combination of above-mentioned any one.
The invention effect
According to the present invention, can provide the curable resin composition of the light and heat with sufficiently long storage period.
Embodiment
Below, at length describe being used for implementing mode of the present invention.
Resin combination in present embodiment is characterized in that, contains (A) acrylic resin, (B) mercaptan compound, (C) latent curing agent, (D) radical polymerization stopper and (E) anionoid polymerization inhibitor.
The acrylic resin of above-mentioned (A) composition is acrylate monomer and/or methacrylate monomer or their oligopolymer.As the acrylate monomer that can use in the present invention and/or methacrylate monomer or their oligopolymer, can following compound be shown example.
Can enumerate: diacrylate and/or the dimethacrylate of three (2-hydroxyethyl) isocyanuric acid ester; Three (2-hydroxyethyl) isocyanuric acid ester triacrylate and/or trimethacrylate; Viscoat 295 and/or trimethacrylate or its oligopolymer; Pentaerythritol triacrylate and/or trimethacrylate or its oligopolymer; The polyacrylic ester of Dipentaerythritol and/or polymethacrylate; Three (acrylyl oxy-ethyl) isocyanuric acid ester; Caprolactone modification three (acrylyl oxy-ethyl) isocyanuric acid ester; Caprolactone modification three (methylacryoyloxyethyl) isocyanuric acid ester; The polyacrylic ester of alkyl-modified Dipentaerythritol and/or polymethacrylate; The polyacrylic ester of caprolactone modification Dipentaerythritol and/or polymethacrylate etc.These can be used alone, and also can be used in combination more than two kinds.
The mercaptan compound of above-mentioned (B) composition is the compound with thiol group, is preferably the compound that every 1 molecule has the thiol group more than 2.From the viewpoint of storage stability, preferred alkaline foreign matter content is the least possible.
As the example of the mercaptan compound of above-mentioned (B) composition, can enumerate: the mercaptan compound that obtains by trimethylolpropane tris (mercaptoethanol acid esters), tetramethylolmethane four (mercaptoethanol acid esters), ethylene glycol bisthioglycolate mercaptoethanol acid esters, trimethylolpropane tris (β-thiopropionate), tetramethylolmethane four (β-thiopropionate), the poly-polyvalent alcohols such as (β-thiopropionates) of Dipentaerythritol and sulfydryl organic acid esterification.These do not need to use on making alkaline matter aspect be preferred.
In addition, as the example of the mercaptan compound of above-mentioned (B) composition, can enumerate: 1,4-butane two mercaptan, 1,5-pentane two mercaptan, 1,6-hexane two mercaptan, 1,8-octane two mercaptan, 1,9-nonane two mercaptan, 1, the alkyl poly-thiol compounds such as 10-decane two mercaptan; The polyethers that contains the end thiol group; The polythioether that contains the end thiol group; The mercaptan compound that reaction by epoxy compounds and hydrogen sulfide obtains; The mercaptan compound with end thiol group that reaction by poly-thiol compound and epoxy compounds obtains; Deng.When using alkaline matter as catalysts in its manufacturing process, preferably carry out dealkalize and process and make alkalimetal ion concentration reach the mercaptan compound that has the thiol group more than two in the following molecule of 50ppm.
The latent curing agent of above-mentioned (C) composition is at room temperature insoluble solid, it is the compound that dissolving occurs and play a role as curing catalyst by heating, as its example, can list under normal temperature is the imidazolium compounds of solid, the solid dispersing amine adduct class curing catalyst of diving, such as the reaction product (urea type adducts class) of reaction product (amine-epoxy adduct class), amine compound and isocyanate compound or the carbamide compound of amine compound and epoxy compounds etc.
be the imidazolium compounds of solid as being used under normal temperature of the present invention, for example can list 2-heptadecyl imidazoles, 2-phenyl-4, the 5-hydroxymethyl-imidazole, the 2-undecyl imidazole, 2 phenyl 4 methyl 5 hydroxy methylimidazole, 2-phenyl-4-benzyl-5-hydroxy methylimidazole, 2, 4-diamino-6-(glyoxal ethyline base-(1))-ethyl-S-triazine, 2, 4-diamino-6-(2 '-methylimidazolyl-(1) ')-ethyl-S-triazine/isocyanuric acid adducts, glyoxal ethyline, the 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyano ethyl-2-phenylimidazole, 1-cyano ethyl-glyoxal ethyline-three trimellitate, 1-cyano ethyl-2-phenylimidazole-three trimellitate, N-(glyoxal ethyline base-1-ethyl)-urea, N, N '-(glyoxal ethyline base-(1)-ethyl)-adipamide etc., but be not limited to these.
Epoxy compounds as one of manufacturing raw material that can be used as the latent curing catalyst (amine-epoxy adduct class) of solid dispersing amine adduct class that uses in the present invention, such as enumerating the polyphenol such as the dihydroxyphenyl propane of sening as an envoy to, Bisphenol F, pyrocatechol, Resorcinol, the perhaps such polyvalent alcohol of glycerine, polyoxyethylene glycol and Epicholorohydrin reaction and the poly epihydric alcohol base ether that obtains; The glycidyl ether-ether that makes the such hydroxycarboxylic acid of P-hydroxybenzoic acid, β oxynaphthoic acid and Epicholorohydrin reaction and obtain; The poly epihydric alcohol base ester that makes the such polycarboxylic acid of phthalic acid, terephthalic acid and Epicholorohydrin reaction and obtain; Make 4, the glycidyl amine compound that 4 '-diaminodiphenyl-methane or Metha Amino Phenon etc. obtain with the Epicholorohydrin reaction; And the polyfunctional epoxy compoundss such as the linear novolac resin of epoxidation phenol, the linear novolac resin of epoxidation cresols, epoxidation polyolefine, the epoxy compounds of the simple functions such as butyl glycidyl base ether, phenylglycidyl ether, glycidyl methacrylate; Deng, but be not limited to these.
Diving that another of curing catalyst made raw material and the amine compound that uses as above-mentioned solid dispersing amine adduct class, can be to have can and have at least the compound that is selected from the functional group in primary amino, secondary amino group and uncle's amino more than 1 in molecule with the active hydrogen of epoxy group(ing) generation addition reaction more than 1 in molecule.The example of such amine compound below is shown, but is not limited to these.That is, for example can list diethylenetriamine, Triethylenetetramine (TETA), Tri N-Propyl Amine, 2-hydroxyethylamino propylamine, cyclo-hexylamine, 4, the aliphatics amine that 4 '-diamino-dicyclohexyl methyl hydride is such; 4, the aromatic amines compounds such as 4 '-diaminodiphenyl-methane, 2-aminotoluene; 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazole quinoline, 2,4-methylimidazole quinoline, piperidines, piperazine etc. contain the heterogeneous ring compound of nitrogen-atoms; Deng.
in addition, wherein, particularly has the compound of uncle's amino in molecule, it is to provide has the raw material that good curing promotes the latent curing catalyst of ability, example as such compound, for example can list dimethylamino propylamine, diethyl amino propylamine, the amino propylamine of diη-propyl, dibutyl amino propyl amine, dimethylamino ethamine, diethylamino ethamine, the amine compound such as N methyl piperazine, glyoxal ethyline, the 2-ethyl imidazol(e), 2-ethyl-4-methylimidazole, the imidazolium compoundss such as 2-phenylimidazole are such, the primary amine or the secondary amine class that have uncle's amino in molecule, DMAE, 1-methyl-DMAE, 1-phenoxymethyl-DMAE, the 2-DEAE diethylaminoethanol, 1-butoxymethyl-DMAE, 1-(2-hydroxyl-3-phenoxy propyl)-glyoxal ethyline, 1-(2-hydroxyl-3-phenoxy propyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxyl-3-butoxy propyl group)-glyoxal ethyline, 1-(2-hydroxyl-3-butoxy propyl group)-2-ethyl-4-methylimidazole, 1-(2-hydroxyl-3-phenoxy propyl)-2-benzylimidazoline, 1-(2-hydroxyl-3-butoxy propyl group)-glyoxal ethyline quinoline, 2-(dimethylaminomethyl) phenol, 2,4,6-three (dimethylaminomethyl) phenol, N-beta-hydroxyethyl morpholine, 2-dimethylaminoethyl alkanethiol, the 2-mercaptopyridine, the 2-benzoglyoxaline, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, the 4-mercaptopyridine, N, the N-dimethylaminobenzoic acid, DMG, nicotinic acid, γ-picolinic acid, picolinic acid, the DMG hydrazides, N, N-dimethyl propylene hydrazides, nicotinic acid hydrazide, Isonicotinoylhydrazine etc. are such, the alcohols that has uncle's amino in molecule, phenols, thio-alcohol, carboxylic-acid and hydrazides class, Deng.
Make the isocyanate compound of raw material as the another one of the curing catalyst of diving as above-mentioned solid dispersing amine adduct class, such as also using the monofunctional isocyanates compounds such as n-butyl isocyanate, n-Isopropyl isocyanate, phenylcarbimide, benzyl mustard oil; Hexamethylene diisocyanate, tolylene diisocyanate, 1,5-naphthalene diisocyanate, ditan-4,4 '-vulcabond, isophorone diisocyanate, xylylene diisocyanate, to phenylene diisocyanate, 1, polyfunctional isocyanate's compounds such as 3,6-hexa-methylene triisocyanate, bicycloheptane triisocyanate; And the compound that contains terminal isocyanate group that obtains of the reaction by these polyfunctional isocyanate's compounds and active dydrogen compounds; Deng.Example as such compound that contains terminal isocyanate group, can list addition compound with terminal isocyanate group that the addition compound with terminal isocyanate group that the reaction by tolylene diisocyanate and TriMethylolPropane(TMP) obtains, the reaction by tolylene diisocyanate and tetramethylolmethane obtain etc., but be not limited to these.
In addition, as carbamide compound, such as can list urea, thiocarbamide etc., but be not limited to these.
can be used for the latent curing catalyst of solid dispersing of the present invention for example can easily be made as follows, namely, with above-mentioned (a) amine compound and these two kinds of compositions of epoxy compounds, (b) these three kinds of compositions of these two kinds of compositions and active dydrogen compounds, perhaps each composition is adopted in the combination of these two kinds or three kinds compositions of (c) amine compound and isocyanate compound and/or carbamide compound, mix, make their reactions at the temperature of room temperature to 200 ℃, then pulverize after cooling curing, perhaps at methyl ethyl ketone, dioxane, make their reactions in the tetrahydrofuran (THF) equal solvent, after desolventizing, solids component is pulverized.
Below illustrate as the latent commercially available typical example of curing catalyst of above-mentioned solid dispersing, but be not limited to these.namely, for example as amine-epoxy adduct class (amine adduct class), can list " Amicure PN-23 " (Ajincomoto Co., Inc's trade(brand)name), " Amicure PN-40 " (Ajincomoto Co., Inc's trade(brand)name), " Amicure PN-50 " (Ajincomoto Co., Inc's trade(brand)name), " Hardener-X-3661S " (A.C.R.Co., Ltd. trade(brand)name), " Hardener-X-3670S " (A.C.R.Co., Ltd. trade(brand)name), " NOVACURE HX-3742 " (Asahi Kasei Corporation's trade(brand)name), " NOVACURE HX-3721 " (Asahi Kasei Corporation's trade(brand)name) etc., in addition, as urea type adducts class, can list " FUJICURE FXE-1000 " (Fuji Kasei Co., Ltd.'s trade(brand)name), " FUJICURE FXR-1030 " (Fuji Kasei Co., Ltd.) etc.
The radical polymerization stopper of above-mentioned (D) composition is the stability during for the preservation that improves resin combination and the material that adds is the material that adds for the generation that suppresses unconscious Raolical polymerizable.
Acrylic resin produces free radical with low probability by self sometimes, sometimes as basic point, unconscious Raolical polymerizable occurs with this free radical.By adding the radical polymerization stopper, thereby can suppress the generation of such unconscious Raolical polymerizable.
The radical polymerization stopper can use known radical polymerization stopper, can use and for example be selected from least a in N-nitroso-group-N-Phenylhydroxylamine aluminium, triphenylphosphine, p methoxy phenol and Resorcinol.In addition, also can use disclosed known radical polymerization stopper in TOHKEMY 2010-117545 communique, TOHKEMY 2008-184514 communique etc.
The anionoid polymerization inhibitor of above-mentioned (E) composition is the stability during for the preservation that improves resin combination and the material that adds is the material that adds for the reaction that suppresses unconscious amino and mercaptan resin.
Latent curing agent (imidazoles, tertiary amine) has amino, and this amino and mercaptan resin react and initiated polymerization.Latent curing agent is designed at room temperature to be difficult to cause the design of amino reaction, although a little, the possibility that but still exists amino at room temperature to react with mercaptan resin.Anionoid polymerization forbid agent amino react with mercaptan resin before with this amino reaction, thereby have the effect of the reaction that suppresses unconscious amino and mercaptan resin.
The anionoid polymerization inhibitor can use known anionoid polymerization inhibitor, for example can use to be selected from least a in boric acid ester, aluminium chelate and organic acid.Boric acid ester for example can use TOHKEMY 2011-026539 communique, disclosed boric acid ester in table 2005/070991 communique again.Aluminium chelate for example can use Japan's disclosed aluminium chelate in table 2005/070991 communique again.Organic acid for example can use disclosed organic acid in No. 4394281 communiques of Japan's special permission.
Resin combination of the present invention preferably also contains (F) radical polymerization initiator.Resin combination solidifies resin combination by containing radical polymerization initiator thereby can shine by the UV of short period of time.Radical polymerization initiator as using in the present invention is not particularly limited, and can use known material.as the concrete example of radical polymerization initiator, for example can list the 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, diethoxy acetophenone, 1-(4-isopropyl phenyl)-2-hydroxy-2-methyl propane-1-ketone, 1-(4-dodecylphenyl)-2-hydroxy-2-methyl propane-1-ketone, 4-(2-hydroxyl-oxethyl)-phenyl (2-hydroxyl-2-propyl group) ketone, 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-morpholino propane-1, bitter almond oil camphor, benzoin methyl ether, the bitter almond oil camphor ethyl ether, the bitter almond oil camphor isopropyl ether, the bitter almond oil camphor n-butyl ether, the bitter almond oil camphor phenyl ether, benzyl dimethyl ketal, benzophenone, benzoylbenzoic acid, the benzoylbenzoic acid methyl esters, the 4-phenyl benzophenone, dihydroxy benaophenonel, propylene acidylate benzophenone, 4-benzoyl-4 '-dimethyl diphenyl sulfide, 3,3 '-dimethyl-4-methoxy benzophenone, thioxanthone, CTX, 2-methyl thioxanthone, 2,4-dimethyl thioxanthone, isopropyl thioxanthone, 2,4-, two clopenthixal ketones, 2,4-diethyl thioxanthone, 2,4-di-isopropyl thioxanthone, 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide, the aminomethyl phenyl oxoethanoic acid, benzyl, camphorquinone etc.
Resin combination of the present invention preferably also contains (G) has the two keys more than two in molecule the compound except acrylic resin.Have the compound except acrylic resin of two keys not how because of heating and mercaptan compound reaction in molecule, therefore, the stability the during preservation that can similarly improve resin combination with the anionoid polymerization inhibitor.
The concrete example that has the compound except acrylic resin of the two keys more than two as (G), can list polyhutadiene, polyvingl ether, have the glycidyl more than two polyhutadiene, have the polyvingl ether of the glycidyl more than two etc.Can also make up in these more than two kinds and use.
For above-mentioned illustrated (A)～(G) composition is prepared for resin combination of the present invention as raw material, not special difficulty, can be according to known method in the past, such as mixing to prepare by utilizing the mixing machines such as Henschel mixer.
For the mercaptan compound of above-mentioned (B) composition, preferably the acrylic resin of above-mentioned (A) composition coordinates in the ratio of equivalence ratio with 0.5～2.0 (more than 0.5 and below 2.0).At this, so-called " equivalence ratio " refers to the equivalent of mercaptan compound and the ratio of the equivalent of acrylic resin.The quality of the mercaptan compound of 1 equivalent equates with the value that the molecular weight of mercaptan compound obtains divided by the quantity of the thiol group in 1 molecule.The quality of the acrylic resin of 1 equivalent equates with the value that the molecular weight of acrylic resin obtains divided by the quantity of the acryl in 1 molecule (or methacryloyl).Namely; the acrylic resin of above-mentioned (A) composition counts 0.5～2.0 with equivalence ratio for the mercaptan compound of above-mentioned (B) composition, refers to that quantity with respect to thiol group is that the quantity of acryl for 1 (methacryloyl) is 0.5～2.0.
By the mixing ratio of above-mentioned (A) acrylic resin with respect to above-mentioned (B) mercaptan compound is set in such scope, thereby the stability the during preservation of resin combination further improves, and can further extend the storage period of resin combination.
In resin combination of the present invention, the content of above-mentioned (D) radical polymerization stopper is preferably 0.0001～1.0wt% for the resin combination total amount.Be set in such scope by the content with above-mentioned (D) radical polymerization stopper, thereby the stability the during preservation of resin combination further improves, and can further extend the storage period of resin combination.
In resin combination of the present invention, the content of above-mentioned (E) anionoid polymerization inhibitor preferably counts 0.001～1.0 with weight ratio for the content of above-mentioned (C) latent curing agent.Be set in such scope by the content with above-mentioned (E) anionoid polymerization inhibitor, thereby the stability the during preservation of resin combination further improves, and can further extend the storage period of resin combination.
Resin combination of the present invention can also contain at least a additive that is selected from silica filler, silane coupling agent, ion-trapping agent, levelling agent, antioxidant, defoamer and thixotropic agent as required.In addition, also can contain viscosity modifier, fire retardant or solvent etc.
Resin combination of the present invention for example can be with acting on caking agent or its raw material that part is engaged with each other.
Resin combination of the present invention for example can be used as, and sealing agent or its raw material of electronic component use.
Embodiment
Below, embodiments of the invention are described, but the present invention is not limited to these.
(preparation of resin combination)
Mix each composition with the cooperation shown in table 1,2, the resin combination in Preparation Example 1～21.
Mix each composition with the cooperation shown in table 3, the resin combination in preparation comparative example 1～2.
Need to prove, in table 1～3, the numeral of the mixing ratio of each composition of expression (A)～(G) all represents with weight part.
In table 1～3, the concrete material name of each composition (A)～(G) etc. are as follows.In addition, the structural formula with the part of (A)～(G) is shown in following [changing 1], [changing 2], [changing 3], [changing 4].
(A1) acrylic resin 1:DAICEL-CYTEC Company, Ltd. system " EBECRYL810 "
Polyester acrylate, weight-average molecular weight be 1000,4 official's energy approximately
(A2) acrylic resin 2: Toagosei Co., Ltd's system " M7100 "
Polyester acrylate, weight-average molecular weight are approximately more than 1000,3 official's energy
(B1) mercaptan compound 1:SC organic chemistry Co., Ltd.'s system " PEMPII "
Tetramethylolmethane four (3-mercaptopropionic acid ester)
(B2) mercaptan compound 2:SC organic chemistry Co., Ltd.'s system " TMMP "
Trimethylolpropane tris (3-mercaptopropionic acid ester), weight-average molecular weight 398
(B3) mercaptan compound 3:SC organic chemistry Co., Ltd.'s system " DPMP "
Dipentaerythritol six (3-mercaptopropionic acid ester), weight-average molecular weight 783
(B4) mercaptan compound 4: Showa Denko K. K's system " Karenz MT "
Tetramethylolmethane four (3-sulfydryl butyric ester), molecular weight 544.8
(C1) latent curing agent 1:Ajinomoto Fine-Techno Co., Inc. system " PN-50 "
(C2) latent curing agent 2:Ajinomoto Fine-Techno Co., Inc. system " PN-23 "
(D1) the radical polymerization stopper 1: Wako Pure Chemical Industries, Ltd.'s system, N-nitroso-group-N-Phenylhydroxylamine aluminium, molecular weight: 488.33
(D2) the radical polymerization stopper 2: Tokyo HuaCheng Industry Co., Ltd's system, triphenylphosphine molecular weight: 262.29
(E1) the anionoid polymerization inhibitor 1: Tokyo HuaCheng Industry Co., Ltd's system, triisopropyl borate ester, molecular weight: 188.07
(E2) anionoid polymerization inhibitor 2:Ajinomoto Fine-Techno Co., Inc. system, aluminium chelate, acetyl alkoxyl group aluminum-diisopropoxide, molecular weight: 496.70
(E3) the anionoid polymerization inhibitor 3: Tokyo HuaCheng Industry Co., Ltd's system, barbituric acid, molecular weight: 128.09
(E4) anionoid polymerization inhibitors 4: Ajinomoto Fine-Techno Co., Inc. system, boric acid ester (triisopropyl borate ester)
(F1) radical polymerization initiator 1:BASF company's system " Lucirin TPO "
Phenylbenzene (2,4,6 trimethoxy benzoyl) phosphine oxide, molecular weight: 348.37
(G1) has the compound except acrylic resin 1 of the two keys more than two: Asahi Denka Co., Ltd.'s system, the polyhutadiene with glycidyl, epoxidation 1,2-polyhutadiene, molecular weight: 1000
(G2) has the compound except acrylic resin 2 of the two keys more than two: Maruzen Petrochemical Co., Ltd.'s system, the polyvingl ether with glycidyl, butyleneglycol mono-vinyl monoglycidyl ether, molecular weight: 172.2
Figure BDA00002889513200121
[table 3]
Figure BDA00002889513200141
Figure BDA00002889513200151
[table 6]
Comparative example 1 2
Outward appearance (heat 80 ℃/20 minutes) ○ ○
Storage period [hour] 0.1 12
Viscosity [mPas] - 580
Linear expansivity [ppm] - -
Modulus in tension (25 ℃) [MPa] - -
Tg(℃) - -
[changing 1]
Figure BDA00002889513200161
[changing 2]
Figure BDA00002889513200171
[changing 3]
Figure BDA00002889513200172
[changing 4]
(based on the curing of heating and the observation of the outward appearance of resulting cured article)
Each resin combination that obtains in embodiment 1～21 and comparative example 1～2 is loaded on the hot plate of 80 ℃ placed 20 minutes.Its result, for all resin combinations of embodiment 1～21 and comparative example 1～2, the resin cured matter that has obtained having good outward appearance.For resulting resin cured matter, penetrate to be confirmed whether to solidify with the stage property of needle-like.Will less than solidify, close to aqueous situation be judged to be *, the situation of having solidified is judged to be zero.Show the result in table 4～6.
(based on the observation of the outward appearance of the curing of UV irradiation and resulting cured article)
For each resin combination of embodiment 1～21 and comparative example 1～2, use the UV irradiating unit of through furnace formula (belt furnace-type), at 400mJ/cm 2Condition under irradiation ultraviolet radiation (UV).Its result for the resin combination of embodiment 1～21, has obtained being cured to the resin cured matter of degree that can be temporary fixed.Particularly in the embodiment 5 that contains radical polymerization initiator, obtained the resin cured matter harder than other embodiment, and be easy to shine by UV and solidify.
(mensuration of storage period)
Measure the storage period of each resin combination of embodiment 1～21 and comparative example 1～2.Its result, as shown in table 4～6, the storage period of each resin combination of embodiment 1～21 is minimum is 24 hours (embodiment 14), has obtained being sufficiently long to the storage period of the degree that can tolerate actual use.With respect to this, be 12 hours to the maximum the storage period of each resin combination of comparative example 1～2 (comparative example 2), do not obtain being sufficiently long to the storage period of the degree that can tolerate actual use.
(mensuration of viscosity)
Measure the viscosity of each resin combination of embodiment 1～21 and comparative example 1～2.
Particularly, the temperature of resin combination is remained on 25 ± 2 ℃, use the TV-22 shape processed viscometer TVE-22H of Toki Sangyo Co., Ltd. (cone rotor: 1 ° 34 ' * R24), the viscosity of mensuration 10rpm.
(mensuration of linear expansivity)
Measure the linear expansivity of each resin combination of embodiment 1～21 and comparative example 1～2.
Particularly, on the stainless steel plate of 40mm * 60mm with stencil (Japanese of stencil is the hole version) coating resin composition so that the thickness when solidifying reaches 150 ± 100 μ m, film thereby form, placed 1 hour under 80 ℃ and make its curing.With this film peel off from stainless steel plate after, cut into specified dimension (5mm * 40mm) with cutting machine.Need to prove, be refined to otch smooth with sand paper.Use Bruker AXS, Inc. heats analytical equipment TMA4000SA series or the device suitable with it, measures this and film under stretch mode, obtains linear expansivity.
(mensuration of modulus in tension)
Measure the modulus in tension of each resin combination of embodiment 1～21 and comparative example 1～2.
Particularly, on the stainless steel plate of 40mm * 60mm with stencil coating resin composition so that the thickness when solidifying reaches 150 ± 100 μ m, film thereby form, placed 1 hour under 80 ℃ and make its curing.With this film peel off from stainless steel plate after, cut into specified dimension (5mm * 40mm) with cutting machine.Need to prove, otch is refined to smooth with sand paper.According to JIS C6481, the Dynamic Thermal machinery mensuration (DMA) of using Seiko Instruments Inc. to make is measured this and is filmed.With this storage Young's modulus of 25 ℃ as modulus in tension.
(mensuration of Tg)
Measure the Tg of each resin combination of embodiment 1～21 and comparative example 1～2.
Particularly, on the stainless steel plate of 40mm * 60mm with stencil coating resin composition so that the thickness when solidifying reaches 150 ± 100 μ m, film thereby form, placed 1 hour under 80 ℃ and make its curing.With this film peel off from stainless steel plate after, cut into specified dimension (5mm * 40mm) with cutting machine.Need to prove, otch is refined to smooth with sand paper.According to JIS C6481, the Dynamic Thermal machinery mensuration (DMA) of using Seiko Instruments Inc. to make is measured this and is filmed.
The measurement result of storage period, viscosity, linear expansivity, modulus in tension and the Tg of embodiment 1～21 and comparative example 1～2 is shown in table 4～6.
(investigation of result)
Observe the result of embodiment 1～21 as can be known, the storage period of resin combination of the present invention is minimum is more than 24 hours, has the sufficiently long storage period of the degree that can tolerate actual use.
With respect to this, comparative example 1,2 resin combination are owing to not containing at least a in radical polymerization stopper and anionoid polymerization inhibitor, therefore, be 12 hours storage period to the maximum, do not have the storage period that is sufficiently long to the degree that can tolerate actual use.
Observe embodiment 1～21 as can be known, for the storage period that obtains more growing, and the content of preferred (E) anionoid polymerization inhibitor counts 0.001～1.0 with weight ratio for the content of (C) latent curing agent.

Claims (13)

1. a resin combination, is characterized in that, contains following A composition～E composition,
A be acrylic resin,
B be mercaptan compound,
C be latent curing agent,
D be the radical polymerization stopper and
E is the anionoid polymerization inhibitor.
2. resin combination according to claim 1, it contains F is radical polymerization initiator.
3. resin combination according to claim 1 and 2, it contains the compound except acrylic resin that G namely has the two keys more than two.
4. resin combination according to claim 3, wherein, the compound except acrylic resin that G namely has the two keys more than two is polyhutadiene.
5. resin combination according to claim 3, wherein, the compound except acrylic resin that G namely has the two keys more than two is polyvingl ether.
6. resin combination according to claim 3, wherein, the compound except acrylic resin that G namely has the two keys more than two is the polyhutadiene with the glycidyl more than two.
7. resin combination according to claim 3, wherein, the compound except acrylic resin that G namely has the two keys more than two is the polyvingl ether with the glycidyl more than two.
8. the described resin combination of any one according to claim 1～7, wherein, A is that acrylic resin/B is that the mercaptan compound equivalence ratio is 0.5～2.0.
9. the described resin combination of any one according to claim 1～8, wherein, described D is that the content of radical polymerization stopper is 0.0001～1.0wt% for the resin combination total amount.
10. the described resin combination of any one according to claim 1～9, wherein, described E is that the content of anionoid polymerization inhibitor counts 0.001～1.0 with weight ratio for the content that C is latent curing agent.
11. the described resin combination of any one according to claim 1～10, wherein, D is that the radical polymerization stopper is to be selected from least a in N-nitroso-group-N-Phenylhydroxylamine aluminium, triphenylphosphine, p methoxy phenol and Resorcinol.
12. the described resin combination of any one according to claim 1～11, wherein, E is that the anionoid polymerization inhibitor is to be selected from least a in boric acid ester, aluminium chelate and organic acid.
13. a caking agent or sealing agent, it contains the described resin combination of any one in claim 1～12.
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JP4976575B1 (en) 2012-07-18
MY156182A (en) 2016-01-15
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WO2013005471A1 (en) 2013-01-10
KR20140032931A (en) 2014-03-17

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Application publication date: 20130508