JP5450386B2 - エポキシ樹脂組成物及び硬化物 - Google Patents
エポキシ樹脂組成物及び硬化物 Download PDFInfo
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- JP5450386B2 JP5450386B2 JP2010505634A JP2010505634A JP5450386B2 JP 5450386 B2 JP5450386 B2 JP 5450386B2 JP 2010505634 A JP2010505634 A JP 2010505634A JP 2010505634 A JP2010505634 A JP 2010505634A JP 5450386 B2 JP5450386 B2 JP 5450386B2
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- epoxy resin
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- epoxy
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- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- PUHCWRBJAFJNPG-UHFFFAOYSA-N ethaneperoxoic acid;ethyl acetate Chemical compound CC(=O)OO.CCOC(C)=O PUHCWRBJAFJNPG-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000004401 flow injection analysis Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000004209 oxidized polyethylene wax Substances 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- ADMFDTHMUXRMJQ-UHFFFAOYSA-N tert-butyl 4-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C([N+]([O-])=O)C=C1 ADMFDTHMUXRMJQ-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- H01L23/293—Organic, e.g. plastic
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy 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
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明のエポキシ樹脂組成物は、エポキシ樹脂、及びエポキシ樹脂用硬化剤を必須成分とし、且つこれら必須成分を樹脂成分の主成分とする。本発明のエポキシ樹脂組成物は無機充填材を含むことができ、この場合は、上記必須成分と無機充填材を主成分とする。
3L反応器にジビニルベンゼン(新日鐵化学製DVB−960ジビニルベンゼン含有量97%、m−体/p−体=62:38)300g、酢酸エチル1200gを装入し撹拌した。次いで、過酢酸30%酢酸エチル溶液1640gを3時間かけて滴下した。滴下中は反応温度を30℃になるように制御を行った。滴下後、さらに30℃にて3時間撹拌を行った。反応液を室温まで冷却した後、20%NaOH水溶液1208gを加え、1時間撹拌後、水層を分離し、未反応の過酢酸及び、生成した酢酸の除去を行った。エバポレーターにて、酢酸エチルを減圧留去した後、ジエポキシエチルベンゼン151.6gを得た(エポキシ樹脂a)。得られた樹脂のエポキシ当量は111g/eq.25℃における粘度は10mPa・s、純度は94.3%(ガスクロマトグラフィー面積%)、m−体/P−体=64:36(1H−NMR積分比)であった。
四つ口セパラブルフラスコにハイドロキノン65g、エピクロルヒドリン546g、ジエチレングリコールジメチルエーテル82gを入れ撹拌溶解させた。均一に溶解後、130mmHgの減圧下65℃に保ち、48%水酸化ナトリウム水溶液98.4gを4時間かけて滴下し、この滴下中に還流留出した水とエピクロルヒドリンを分離槽で分離しエピクロルヒドリンは反応容器に戻し、水は系外に除いて反応した。反応終了後、濾過により生成した塩を除き、更に水洗したのちエピクロルヒドリンを留去し、エポキシ樹脂120gを得た(エポキシ樹脂b)。得られた樹脂のエポキシ当量は116g/eq.、融点は100℃であった。
下記に示すエポキシ樹脂、硬化剤、無機充填材と、硬化促進剤としてトリフェニルホスフィンを用い、表1に示す配合割合で混練してエポキシ樹脂組成物を調製した。
Claims (3)
- エポキシ樹脂、エポキシ樹脂用硬化剤及び無機充填材を含有するエポキシ樹脂組成物において、エポキシ樹脂として、下記一般式(1)で表わされ、2個のエポキシエチル基の置換位置が1,3−ジ置換体及び1,4−ジ置換体であるエポキシ化合物を合計で90重量%以上含有し、25℃での粘度が50mPa・s以下であるエポキシ樹脂を使用し、エポキシ樹脂用硬化剤として、軟化点が40〜150℃であるフェノールノボラック樹脂を使用すること、組成物(無機充填材を除いた状態)としたときの粘度が25℃で0.01〜100Pa・sであること、及び無機充填材を83重量%以上含有することを特徴とする電気・電子部品封止用のエポキシ樹脂組成物。
- 一般式(1)で表わされるエポキシ樹脂の1,3−ジ置換体と1,4−ジ置換体の存在割合(モル比)が1:9〜9:1の範囲である請求項1に記載のエポキシ樹脂組成物。
- 請求項1又は2に記載のエポキシ樹脂組成物を硬化してなることを特徴とするエポキシ樹脂硬化物。
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JP5478603B2 (ja) * | 2009-03-05 | 2014-04-23 | 新日鉄住金化学株式会社 | エポキシ樹脂組成物 |
US20110122590A1 (en) * | 2009-11-23 | 2011-05-26 | Dow Global Technologies Inc. | Epoxy resin formulations for underfill applications |
CN102666637B (zh) * | 2009-11-23 | 2015-05-20 | 陶氏环球技术有限责任公司 | 增韧环氧树脂配制剂 |
KR20120114295A (ko) * | 2009-12-09 | 2012-10-16 | 다우 글로벌 테크놀로지스 엘엘씨 | 에폭시 수지 조성물 |
CN102762628A (zh) * | 2010-02-19 | 2012-10-31 | 陶氏环球技术有限责任公司 | 二乙烯基芳烃二氧化物树脂组合物 |
TW201139395A (en) * | 2010-03-24 | 2011-11-16 | Dow Global Technologies Llc | Process for preparing divinylarene dioxides |
JP2012092247A (ja) * | 2010-10-28 | 2012-05-17 | Showa Denko Kk | 液状硬化性組成物 |
JP5676008B2 (ja) * | 2010-11-22 | 2015-02-25 | ダウ グローバル テクノロジーズ エルエルシー | 強靱化剤としてdvbdoの付加物を含むエポキシ樹脂 |
JP5909318B2 (ja) * | 2010-12-07 | 2016-04-26 | ナミックス株式会社 | 電子部品実装体、および電子部品の実装方法 |
EP2707411B1 (en) * | 2011-05-13 | 2015-09-30 | Dow Global Technologies LLC | Insulation formulations |
EP4028378A4 (en) | 2019-09-10 | 2024-03-13 | Countertrace LLC | HEXASUBSTITUTED BENZENES, SURFACES MODIFIED THEREBY, AND ASSOCIATED METHODS |
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JPH04359009A (ja) * | 1991-06-05 | 1992-12-11 | Nippon Steel Chem Co Ltd | 低粘度エポキシ樹脂及びその組成物 |
JPH1171364A (ja) * | 1997-05-16 | 1999-03-16 | Natl Starch & Chem Investment Holding Corp | 活性放射線または熱開始カチオン硬化性エポキシドモノマー及びそれらのモノマーから製造された組成物 |
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US2912389A (en) * | 1957-08-08 | 1959-11-10 | Union Carbide Corp | Polymers of divinylbenzene dioxide |
US2924580A (en) * | 1957-08-08 | 1960-02-09 | Union Carbide Corp | Divinyl benzene dioxide compositions |
JPH0453821A (ja) * | 1990-06-21 | 1992-02-21 | Toray Ind Inc | 熱硬化性樹脂組成物 |
JP4067916B2 (ja) * | 2002-08-26 | 2008-03-26 | 新日鐵化学株式会社 | 液状エポキシ樹脂組成物 |
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- 2009-03-23 JP JP2010505634A patent/JP5450386B2/ja active Active
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JPH04359009A (ja) * | 1991-06-05 | 1992-12-11 | Nippon Steel Chem Co Ltd | 低粘度エポキシ樹脂及びその組成物 |
JPH1171364A (ja) * | 1997-05-16 | 1999-03-16 | Natl Starch & Chem Investment Holding Corp | 活性放射線または熱開始カチオン硬化性エポキシドモノマー及びそれらのモノマーから製造された組成物 |
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