JPH06287409A - Liquid epoxy resin composition - Google Patents
Liquid epoxy resin compositionInfo
- Publication number
- JPH06287409A JPH06287409A JP9678193A JP9678193A JPH06287409A JP H06287409 A JPH06287409 A JP H06287409A JP 9678193 A JP9678193 A JP 9678193A JP 9678193 A JP9678193 A JP 9678193A JP H06287409 A JPH06287409 A JP H06287409A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- liquid
- inorganic filler
- resin composition
- acid derivative
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 title claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 27
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 26
- 239000011256 inorganic filler Substances 0.000 claims abstract description 26
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 239000003822 epoxy resin Substances 0.000 claims description 33
- 229920000647 polyepoxide Polymers 0.000 claims description 33
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 125000004018 acid anhydride group Chemical group 0.000 claims 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 abstract description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 13
- 229910002026 crystalline silica Inorganic materials 0.000 abstract description 5
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 5
- 238000001556 precipitation Methods 0.000 abstract description 4
- 238000007789 sealing Methods 0.000 abstract description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 abstract 1
- 229910001679 gibbsite Inorganic materials 0.000 abstract 1
- QIVRABJQTNPYAI-QFIPXVFZSA-N (2s)-n,n'-dibutyl-2-(dodecanoylamino)pentanediamide Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(=O)NCCCC)CCC(=O)NCCCC QIVRABJQTNPYAI-QFIPXVFZSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- -1 glycidyl ester Chemical class 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009974 thixotropic effect Effects 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LHXNVCCLDTYJGT-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)propan-2-ol Chemical compound CC(O)COCC1CO1 LHXNVCCLDTYJGT-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- XYXBMCIMPXOBLB-UHFFFAOYSA-N 3,4,5-tris(dimethylamino)-2-methylphenol Chemical compound CN(C)C1=CC(O)=C(C)C(N(C)C)=C1N(C)C XYXBMCIMPXOBLB-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、液状エポキシ樹脂組成
物に関するものである。FIELD OF THE INVENTION The present invention relates to a liquid epoxy resin composition.
【０００２】[0002]
【従来の技術】従来、電気・電子部品の注型封止用やシ
ーリング用に、無機フィラーを含有する液状エポキシ樹
脂組成物を用いることは広く知られている。このような
液状エポキシ樹脂組成物においては、無機フィラーの比
重がエポキシ樹脂や硬化剤の比重より大きいと、貯蔵中
に無機フィラーが沈降するという問題を生じる。このよ
うな無機フィラーの沈降は、得られるエポキシ樹脂製品
中の無機フィラーの分散を不均一のものにするため、製
品物性の悪化の原因となる。従来、前記した無機フィラ
ーの沈降を防止するために、超微粒子シリカ、疎水性シ
リカ、有機ベントナイト等のチキソトロピー付与剤を配
合することが行われてきた。しかし、チキソトロピー付
与剤を配合した組成物は、一般に、そのチキソトロピー
性の経時変化が大きく、経時によりチキソトロピー性が
大きく低下するため、無機フィラーの沈降を防止するこ
とは著しく困難であった。2. Description of the Related Art Conventionally, it has been widely known to use a liquid epoxy resin composition containing an inorganic filler for casting and sealing of electric / electronic parts. In such a liquid epoxy resin composition, when the specific gravity of the inorganic filler is higher than the specific gravity of the epoxy resin or the curing agent, the inorganic filler precipitates during storage. Such sedimentation of the inorganic filler makes the dispersion of the inorganic filler in the obtained epoxy resin product non-uniform, which causes deterioration of the physical properties of the product. Conventionally, in order to prevent the above-mentioned precipitation of the inorganic filler, a thixotropy imparting agent such as ultrafine particle silica, hydrophobic silica and organic bentonite has been blended. However, a composition containing a thixotropy-imparting agent generally has a large change in its thixotropy with time, and its thixotropy significantly decreases with time, so that it is extremely difficult to prevent the precipitation of the inorganic filler.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、無機フィラ
ーの沈降が効果的に防止された液状エポキシ樹脂組成物
を提供することをその課題とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a liquid epoxy resin composition in which sedimentation of an inorganic filler is effectively prevented.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、前記課題
を解決すべく鋭意研究を重ねた結果、特定のグルタミン
酸誘導体と水酸化アルミニウムの組合せを沈降防止剤と
して使用することにより、前記課題を解決し得ることを
見出し、本発明を完成するに至った。即ち、本発明によ
れば、液状エポキシ樹脂を含有する第１液と、硬化剤と
無機フィラーを含有する第２液とから構成されるエポキ
シ樹脂組成物において、該第２液中に、無機フィラーの
沈降防止剤として、一般式、 （式中、Ｒ1は高級アルキル基又はアルケニル基、Ｒ2、
Ｒ3は低級アルキル基を示す）で表わされるグルタミン
酸誘導体と水酸化アルミニウムの組合せを添加したこと
を特徴とするエポキシ樹脂組成物が提供される。また、
本発明によれば、エポキシ樹脂と、酸無水物と、無機フ
ィラーを含有する一液性エポキシ樹脂組成物において、
無機フィラーの沈降防止剤として、一般式、 （式中、Ｒ1は高級アルキル基又はアルケニル基、Ｒ2、
Ｒ3は低級アルキル基を示す）で表わされるグルタミン
酸誘導体と水酸化アルミニウムの組合せを含有すること
を特徴とする液状エポキシ樹脂組成物が提供される。Means for Solving the Problems
As a result of repeated studies to solve the problem, specific glutamine
A combination of an acid derivative and aluminum hydroxide with an antisettling agent
Can be used to solve the above problems
Heading out, the present invention has been completed. That is, according to the present invention
Then, the first liquid containing the liquid epoxy resin and the curing agent
Epoxy composed of a second liquid containing an inorganic filler
In the resin composition, in the second liquid, an inorganic filler
As an anti-settling agent, a general formula, (In the formula, R1Is a higher alkyl group or alkenyl group, R2,
R3Is a lower alkyl group)
Adding a combination of acid derivative and aluminum hydroxide
An epoxy resin composition is provided. Also,
According to the present invention, an epoxy resin, an acid anhydride, and an inorganic resin are used.
In a one-pack type epoxy resin composition containing a filler,
As a settling agent for inorganic fillers, a general formula, (In the formula, R1Is a higher alkyl group or alkenyl group, R2,
R3Is a lower alkyl group)
Containing a combination of acid derivative and aluminum hydroxide
A liquid epoxy resin composition is provided.
【０００５】本発明で用いる液状エポキシ樹脂は、１分
子中に２個以上のエポキシ基を有する常温で液状を示す
ものであれば任意のものを使用することができる。この
ようなエポキシ樹脂としては、例えば、ビスフェノール
Ａ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、
ビスフェノールＳ型エポキシ樹脂、フェノールボラック
型エポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキ
シ樹脂、グリシジルエステル型エポキシ樹脂、グリシジ
ルアミン系エポキシ樹脂、含ブロムエポキシ樹脂、水添
ビスフェノールＡ型エポキシ樹脂、プロピレングリコー
ルグリシジルエーテルなどの脂肪族エポキシ樹脂、ウレ
タン変性エポキシ樹脂等が挙げられ、これらのエポキシ
樹脂は２種以上混合して用いても良い。また、必要に応
じて、ブチルグリシジルエーテル、フェニルグリシジル
エーテル、クレシルグリシジルエーテル、脂肪族アルコ
ールのグリシジルエーテルなどのようなモノ及びジエポ
キシ化合物を配合して用いてもよいし、常温固体状のエ
ポキシ樹脂を適量配合して用いてもよい。As the liquid epoxy resin used in the present invention, any one may be used as long as it has two or more epoxy groups in one molecule and exhibits a liquid state at room temperature. Examples of such epoxy resin include bisphenol A type epoxy resin, bisphenol F type epoxy resin,
Bisphenol S type epoxy resin, phenolvolac type epoxy resin, alicyclic epoxy resin, heterocyclic epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, brominated epoxy resin, hydrogenated bisphenol A type epoxy resin, Examples thereof include aliphatic epoxy resins such as propylene glycol glycidyl ether, urethane-modified epoxy resins, and the like, and these epoxy resins may be used as a mixture of two or more kinds. Further, if necessary, mono- and diepoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, and glycidyl ether of aliphatic alcohol may be blended and used, or an epoxy resin which is solid at room temperature. May be used in an appropriate amount.
【０００６】本発明で用いる硬化剤としては、常温で液
状を示すものであればよく、従来公知の各種のものが用
いられる。このような硬化剤としては、酸無水物や、ポ
リオキシアルキレンアミン等の使用が好ましい。酸無水
物の具体例としては、例えば、ドデセニル無水コハク
酸、メチルテトラヒドロ無水フタル酸、メチルナジック
酸無水物、メチルヘキサヒドロ無水フタル酸などが挙げ
られる。これらのものは１種又は２種以上混合して用い
ても良い。また、必要に応じて、無水マレイン酸、ヘキ
サヒドロ無水フタル酸、無水トリメリット酸、無水ピロ
メリット酸等を配合することもできる。さらに、前記酸
無水物は、公知の硬化促進剤、例えば、トリスジメチル
アミノメチルフェノール、ベンジルジメチルアミン、イ
ミダゾール誘導体などと共に用いることができる。The curing agent used in the present invention may be any one that is liquid at room temperature, and various conventionally known ones may be used. As such a curing agent, it is preferable to use an acid anhydride or polyoxyalkylene amine. Specific examples of the acid anhydride include dodecenyl succinic anhydride, methyltetrahydrophthalic anhydride, methylnadic acid anhydride, methylhexahydrophthalic anhydride and the like. You may use these 1 type or in mixture of 2 or more types. In addition, maleic anhydride, hexahydrophthalic anhydride, trimellitic anhydride, pyromellitic dianhydride, etc. can be blended if necessary. Further, the acid anhydride can be used together with a known curing accelerator such as trisdimethylaminomethylphenol, benzyldimethylamine, and an imidazole derivative.
【０００７】ポリオキシアルキレンアミンとしては、例
えば、以下の一般式で表わされるものが好ましく用いら
れる。 （式中、Ｒ4、Ｒ5は水素又はメチル基を示し、ｎは１以
上の整数を示す） （式中、ｍは１以上の整数を示す）Examples of polyoxyalkylene amines include
For example, those represented by the following general formula are preferably used.
Be done. (In the formula, RFour, RFiveRepresents hydrogen or a methyl group, and n is 1 or more.
Indicates the upper integer) (In the formula, m represents an integer of 1 or more)
【化１】 （前記式中、ｘ、ｙ、ｚは１以上の整数を表わす）[Chemical 1] (In the above formula, x, y and z represent an integer of 1 or more)
【０００８】本発明で用いる無機フィラーとしては、エ
ポキシ樹脂組成物に慣用されている各種のものを用いる
ことができ、その種類は特に制約されない。このような
ものとしては、例えば、溶融性シリカ、結晶性シリカ、
タルク、カオリン、炭酸カルシウム、炭酸マグネシウ
ム、アルミナ、シリカ、ケイ酸カルシウム等が挙げられ
る。無機フィラーの平均粒径は、通常、１〜１００μ
ｍ、好ましくは５〜２０μｍである。As the inorganic filler to be used in the present invention, various kinds commonly used in epoxy resin compositions can be used, and the kind thereof is not particularly limited. As such, for example, fusible silica, crystalline silica,
Examples thereof include talc, kaolin, calcium carbonate, magnesium carbonate, alumina, silica, calcium silicate and the like. The average particle size of the inorganic filler is usually 1 to 100 μm.
m, preferably 5 to 20 μm.
【０００９】本発明において沈降防止剤の一方の成分と
して用いるグルタミン酸誘導体は、前記一般式（１）で
表されるものである。前記一般式（１）において、Ｒ1
は、炭素数８〜２２のアルキル基又はアルケニル基であ
ることができ、このようなものには、オクチル基、ラウ
リル基、ドデシル基、ミリスチル基、ステアリル基、オ
レイル基、リノレイル基等が挙げられる。また、Ｒ2、
Ｒ3としては、炭素数１〜６、好ましくは２〜４の低級
アルキル基であることができる。The glutamic acid derivative used as one component of the anti-settling agent in the present invention is represented by the above general formula (1). In the general formula (1), R 1
May be an alkyl group or an alkenyl group having 8 to 22 carbon atoms, and examples thereof include an octyl group, a lauryl group, a dodecyl group, a myristyl group, a stearyl group, an oleyl group, and a linoleyl group. . Also, R 2 ,
R 3 may be a lower alkyl group having 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms.
【００１０】本発明において用いる沈降防止剤の他方の
成分としては、水酸化アルミニウムが用いられる。この
水酸化アルミとしては一般的にエポキシ樹脂用充填剤と
して使用されているものであればよく、ボーキサイトを
原料として、バイヤー法により製造される白色粉末のも
のが好ましく用いられ、その平均粒径は、０．６〜１８
μｍ、好ましくは１．０〜８μｍである。Aluminum hydroxide is used as the other component of the antisettling agent used in the present invention. The aluminum hydroxide may be one that is generally used as a filler for epoxy resins, and white powder produced by the Bayer method using bauxite as a raw material is preferably used, and its average particle size is , 0.6-18
μm, preferably 1.0 to 8 μm.
【００１１】本発明の液状エポキシ樹脂組成物におい
て、硬化剤の使用量は、その官能基当量で、エポキシ樹
脂のエポキシ基１当量当り、０．８〜１．２当量、好ま
しくは０．９〜１．１当量である。無機フィラーの使用
量は、エポキシ樹脂１００重量部当り、１０重量部以
上、好ましくは１００〜２３０重量部である。In the liquid epoxy resin composition of the present invention, the amount of the curing agent used is 0.8 to 1.2 equivalents, preferably 0.9 to 1.2 equivalents of the functional groups per equivalent of epoxy groups of the epoxy resin. 1.1 equivalents. The amount of the inorganic filler used is 10 parts by weight or more, preferably 100 to 230 parts by weight, per 100 parts by weight of the epoxy resin.
【００１２】本発明の液状エポキシ樹脂組成物は、一液
性エポキシ樹脂組成物及び二液性エポキシ樹脂組成物で
あることができる。二液性エポキシ樹脂組成物は、液状
エポキシ樹脂を含む第１液と、硬化剤と無機フィラーを
含有する第２液とから構成されるが、本発明による沈降
防止剤は、第２液に添加する。この場合、沈降防止剤の
添加量は、第２液中、グルタミン酸誘導体の場合、０．
１〜１０重量％、好ましくは０．５〜２重量％であり、
水酸化アルミニウムの場合、５〜１０重量％である。ま
た、水酸化アルミニウム１重量部に対するグルタミン酸
誘導体の重量割合は、０．０１〜２重量部、好ましくは
０．０５〜０．４重量部である。第１液を液状エポキシ
樹脂と無機フィラーとで構成し、これに本発明による沈
降防止剤を添加しても、無機フィラーに対する格別の沈
降防止効果を得ることができない。The liquid epoxy resin composition of the present invention can be a one-part epoxy resin composition and a two-part epoxy resin composition. The two-component epoxy resin composition is composed of a first liquid containing a liquid epoxy resin and a second liquid containing a curing agent and an inorganic filler. The antisettling agent according to the present invention is added to the second liquid. To do. In this case, the amount of the anti-settling agent added was 0.2% for the glutamic acid derivative in the second liquid.
1 to 10% by weight, preferably 0.5 to 2% by weight,
In the case of aluminum hydroxide, it is 5 to 10% by weight. The weight ratio of the glutamic acid derivative to 1 part by weight of aluminum hydroxide is 0.01 to 2 parts by weight, preferably 0.05 to 0.4 parts by weight. Even if the first liquid is composed of a liquid epoxy resin and an inorganic filler, and the anti-settling agent according to the present invention is added thereto, a particular anti-settling effect on the inorganic filler cannot be obtained.
【００１３】本発明による一液性エポキシ樹脂組成物
は、液状エポキシ樹脂と、硬化剤としての酸無水物と、
無機フィラーと、沈降防止剤としてのグルタミン酸誘導
体と水酸化アルミニウムを含有するものである。グルタ
ミン酸誘導体の添加量は、全組成物中、０．１〜１重量
％、好ましくは０．２〜０．５重量％であり、水酸化ア
ルミニウムの添加量は、全組成物中、１〜１０重量％、
好ましくは２〜５重量％である。また、水酸化アルミニ
ウム１重量部当りのグルタミン酸誘導体の使用量は、
０．０１〜１重量部、好ましくは０．０４〜０．８重量
部である。この一液性組成物において、硬化剤としてポ
リオキシアルキルアミンを用いるときには、良好な沈降
防止効果を得ることができない。The one-component epoxy resin composition according to the present invention comprises a liquid epoxy resin, an acid anhydride as a curing agent, and
It contains an inorganic filler, a glutamic acid derivative as an anti-settling agent, and aluminum hydroxide. The amount of the glutamic acid derivative added is 0.1 to 1% by weight, preferably 0.2 to 0.5% by weight, based on the total composition, and the amount of aluminum hydroxide added is 1 to 10% based on the total composition. weight%,
It is preferably 2 to 5% by weight. The amount of the glutamic acid derivative used per 1 part by weight of aluminum hydroxide is
It is 0.01 to 1 part by weight, preferably 0.04 to 0.8 part by weight. In this one-pack composition, when a polyoxyalkylamine is used as a curing agent, a good anti-settling effect cannot be obtained.
【００１４】[0014]
【実施例】次に本発明を実施例によりさらに詳細に説明
する。なお、以下において示した初期粘度、チキソトロ
ピックインデックス及びフィラーの沈降性は、以下のよ
うにして測定されたものである。また、以下において示
す部はいずれも重量部である。 （初期粘度）ブルックフィールドＨＢＴ型回転粘度計に
て組成物の液温２５℃の粘度を測定した。 （チキソトロピックインデックス）ブルックフィールド
ＨＢＴ型回転粘度計にて、所定のスピンドルを用いて回
転数２．５ｒｐｍと２０ｒｐｍの２５℃における各粘度
の測定値の比を求めた。 （フィラーの沈降性）試料約５００ｃｃを金属製の容器
（高さ１１０ｍｍ×８５φ）に入れ２５℃で２０日後に
試料にスパチュラを突きさし、試料の沈降層の有無及び
堅さを調べた。 （評価基準） ○：沈降層は認められなかった。 △：ソフトな沈降が認められた。 ×：容器の下側にケーキング層が認められた。EXAMPLES Next, the present invention will be described in more detail by way of examples. The initial viscosity, the thixotropic index, and the sedimentation property of the filler shown below are measured as follows. Moreover, all parts shown below are parts by weight. (Initial Viscosity) The viscosity of the composition at a liquid temperature of 25 ° C. was measured with a Brookfield HBT type rotational viscometer. (Thixotropic Index) A Brookfield HBT rotational viscometer was used to determine the ratio of the measured values of the respective viscosities at a rotation speed of 2.5 rpm and 20 rpm at 25 ° C. using a predetermined spindle. (Sedimentability of Filler) About 500 cc of a sample was placed in a metal container (height 110 mm × 85φ), and after 20 days at 25 ° C., a spatula was pierced on the sample to examine the presence or absence of a sedimented layer and the hardness of the sample. (Evaluation Criteria) A: No sedimented layer was observed. Δ: Soft sedimentation was observed. X: A caking layer was found on the lower side of the container.
【００１５】実施例１ ビスフェノールＡ型エポキシ樹脂（エポキシ当量：１９
０）：９０部に、モノグルシジルエーテル：１０部、結
晶性シリカ（平均粒径：６μｍ）２７０部、メチルテト
ラヒドロ無水フタル酸：７７部、硬化促進剤（三塩化ホ
ウ素アミン）：１部、シリコーン消泡剤：０．０１部、
水酸化アルミニウム：１０部、グルタミン酸誘導体（Ｇ
Ｐ−１）（平均粒径：１２μｍ）：１部からなる混合成
分を均一に混合して、一液性エポキシ樹脂組成物を調製
し、この組成物を用いてその性能を測定した。その結果
を表１に示す。なお、前記したグルタミン酸誘導体（Ｇ
Ｐ−１）は次式で表わされるもので、「油ゲル化剤ＧＰ
−１」として味の素（株）により販売されているもので
ある。 Example 1 Bisphenol A type epoxy resin (epoxy equivalent: 19
0): 90 parts, monoglycidyl ether: 10 parts, crystalline silica (average particle size: 6 μm) 270 parts, methyltetrahydrophthalic anhydride: 77 parts, curing accelerator (boron trichloride amine): 1 part, Silicone antifoaming agent: 0.01 part,
Aluminum hydroxide: 10 parts, glutamic acid derivative (G
P-1) (average particle size: 12 μm): A mixing component consisting of 1 part was uniformly mixed to prepare a one-pack type epoxy resin composition, and the performance was measured using this composition. The results are shown in Table 1. The glutamic acid derivative (G
P-1) is represented by the following formula: "Oil gelling agent GP
-1 ”is sold by Ajinomoto Co., Inc.
【００１６】比較例１−１ 実施例１において、グルタミン酸誘導体（ＧＰ−１）を
添加しない以外は同様にして組成物を調製し、その性能
を測定した。その結果を表１に示す。Comparative Example 1-1 A composition was prepared in the same manner as in Example 1 except that the glutamic acid derivative (GP-1) was not added, and its performance was measured. The results are shown in Table 1.
【００１７】比較例１−２ 実施例１において、水酸化アルミニウムを添加しない以
外は同様にして組成物を調製し、その性能を測定した。
その結果を表１に示す。Comparative Example 1-2 A composition was prepared in the same manner as in Example 1 except that aluminum hydroxide was not added, and its performance was measured.
The results are shown in Table 1.
【００１８】比較例１−３ 実施例１において、グルタミン酸誘導体（ＧＰ−１）と
水酸化アルミニウムの両方を添加しない以外は同様にし
て組成物を調製し、その性能を測定した。その結果を表
１に示す。Comparative Example 1-3 A composition was prepared in the same manner as in Example 1 except that neither the glutamic acid derivative (GP-1) nor aluminum hydroxide was added, and its performance was measured. The results are shown in Table 1.
【００１９】[0019]
【表１】 [Table 1]
【００２０】実施例２ 二液性エポキシ樹脂組成物における第２液を得るため
に、ジエファーミンＤ−２００：３４部、シリコン消泡
剤：０．０１部、結晶性シリカ（平均粒径：６μｍ）：
６０部、水酸化アルミニウム：６部、グルタミン酸誘導
体（ＧＰ−１）：０．５部を均一に混合した。この混合
液の性能を測定し、その結果を表２に示す。なお、前記
ジエファーミンＤ−２００は、前記一般式（３）で表さ
れるｍが平均３３の、平均分子量２０００の化合物であ
り、三石テキサコケミカル（株）により販売されている
ものである。Example 2 To obtain the second liquid in the two-component epoxy resin composition, Difermin D-200: 34 parts, Silicon antifoaming agent: 0.01 part, crystalline silica (average particle size: 6 μm) :
60 parts, aluminum hydroxide: 6 parts, and glutamic acid derivative (GP-1): 0.5 part were uniformly mixed. The performance of this mixed solution was measured, and the results are shown in Table 2. The diefermin D-200 is a compound represented by the general formula (3) having an average m of 33 and an average molecular weight of 2000, and is sold by Mitsuishi Texaco Chemical Co., Ltd.
【００２１】比較例２−１ 実施例２において、グルタミン酸誘導体（ＧＰ−１）を
添加しない以外は同様にして第２液を調製し、その性能
を測定した。その結果を表２に示す。Comparative Example 2-1 A second liquid was prepared in the same manner as in Example 2 except that the glutamic acid derivative (GP-1) was not added, and its performance was measured. The results are shown in Table 2.
【００２２】比較例２−２ 実施例２において、水酸化アルミニウムを添加しない以
外は同様にして第２液を調製し、その性能を測定した。
その結果を表２に示す。Comparative Example 2-2 A second liquid was prepared in the same manner as in Example 2 except that aluminum hydroxide was not added, and its performance was measured.
The results are shown in Table 2.
【００２３】比較例２−３ 実施例２において、グルタミン酸誘導体（ＧＰ−１）と
水酸化アルミニウムの両方を添加しない以外は同様にし
て第２液を調製し、その性能を測定した。その結果を表
２に示す。Comparative Example 2-3 A second liquid was prepared in the same manner as in Example 2 except that neither the glutamic acid derivative (GP-1) nor aluminum hydroxide was added, and its performance was measured. The results are shown in Table 2.
【００２４】[0024]
【表２】 [Table 2]
【００２５】実施例３ 二液性エポキシ樹脂組成物における第２液を得るため
に、メチルテトラヒドロ無水フタル酸：３３部、ベンジ
ルジメチルアミン：１部、シリコン消泡剤：０．０１
部、結晶性シリカ（平均粒径：６μｍ）：６０部、水酸
化アルミニウム（平均粒径：８μｍ）：６部、グルタミ
ン酸誘導体（ＧＰ−１）：１部を均一に混合した。この
混合液の性能を測定し、その結果を表３に示す。Example 3 To obtain the second liquid in the two-part epoxy resin composition, methyl tetrahydrophthalic anhydride: 33 parts, benzyldimethylamine: 1 part, silicone antifoaming agent: 0.01
Parts, crystalline silica (average particle size: 6 μm): 60 parts, aluminum hydroxide (average particle size: 8 μm): 6 parts, glutamic acid derivative (GP-1): 1 part were uniformly mixed. The performance of this mixed solution was measured, and the results are shown in Table 3.
【００２６】比較例３−１ 実施例３において、グルタミン酸誘導体（ＧＰ−１）を
添加しない以外は同様にして第２液を調製し、その性能
を測定した。その結果を表３に示す。Comparative Example 3-1 A second liquid was prepared in the same manner as in Example 3 except that the glutamic acid derivative (GP-1) was not added, and its performance was measured. The results are shown in Table 3.
【００２７】比較例３−２ 実施例３において、水酸化アルミニウムを添加しない以
外は同様にして第２液を調製し、その性能を測定した。
その結果を表３に示す。Comparative Example 3-2 A second liquid was prepared in the same manner as in Example 3 except that aluminum hydroxide was not added, and its performance was measured.
The results are shown in Table 3.
【００２８】比較例３−３ 実施例３において、グルタミン酸誘導体（ＧＰ−１）と
水酸化アルミニウムの両方を添加しない以外は同様にし
て第２液を調製し、その性能を測定した。その結果を表
３に示す。Comparative Example 3-3 A second liquid was prepared in the same manner as in Example 3 except that neither the glutamic acid derivative (GP-1) nor aluminum hydroxide was added, and its performance was measured. The results are shown in Table 3.
【００２９】[0029]
【表３】 [Table 3]
【手続補正書】[Procedure amendment]
【提出日】平成５年５月２１日[Submission date] May 21, 1993
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１３[Correction target item name] 0013
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１３】本発明による一液性エポキシ樹脂組成物
は、液状エポキシ樹脂と、硬化剤としての酸無水物と、
無機フィラーと、沈降防止剤としてのグルタミン酸誘導
体と水酸化アルミニウムを含有するものである。グルタ
ミン酸誘導体の添加量は、全組成物中、０．１〜１重量
％、好ましくは０．２〜０．５重量％であり、水酸化ア
ルミニウムの添加量は、全組成物中、１〜１０重量％、
好ましくは２〜５重量％である。また、水酸化アルミニ
ウム１重量部当りのグルタミン酸誘導体の使用量は、
０．０１〜１重量部、好ましくは０．０４〜０．８重量
部である。The one-component epoxy resin composition according to the present invention comprises a liquid epoxy resin, an acid anhydride as a curing agent, and
It contains an inorganic filler, a glutamic acid derivative as an anti-settling agent, and aluminum hydroxide. The amount of the glutamic acid derivative added is 0.1 to 1% by weight, preferably 0.2 to 0.5% by weight, based on the total composition, and the amount of aluminum hydroxide added is 1 to 10% based on the total composition. weight%,
It is preferably 2 to 5% by weight. The amount of the glutamic acid derivative used per 1 part by weight of aluminum hydroxide is
It is 0.01 to 1 part by weight, preferably 0.04 to 0.8 part by weight.
Claims (3)
硬化剤と無機フィラーを含有する第２液とから構成され
る液状エポキシ樹脂組成物において、該第２液中に、無
機フィラーの沈降防止剤として、一般式、 （式中、Ｒ1は高級アルキル基又はアルケニル基、Ｒ2、
Ｒ3は低級アルキル基を示す）で表わされるグルタミン
酸誘導体と水酸化アルミニウムの組合せを添加したこと
を特徴とする液状エポキシ樹脂組成物。1. A first liquid containing a liquid epoxy resin,
Comprised of a curing agent and a second liquid containing an inorganic filler
A liquid epoxy resin composition containing
As an anti-settling agent for machine filler, a general formula, (In the formula, R1Is a higher alkyl group or alkenyl group, R2,
R3Is a lower alkyl group)
Adding a combination of acid derivative and aluminum hydroxide
A liquid epoxy resin composition comprising:
キレンアミンである請求項１の組成物。2. The composition according to claim 1, wherein the curing agent is an acid anhydride or a polyoxyalkylene amine.
ラーを含有する一液性エポキシ樹脂組成物において、無
機フィラーの沈降防止剤として、一般式、 （式中、Ｒ1は高級アルキル基又はアルケニル基、Ｒ2、
Ｒ3は低級アルキル基を示す）で表わされるグルタミン
酸誘導体と水酸化アルミニウムの組合せを含有すること
を特徴とする液状エポキシ樹脂組成物。3. An epoxy resin, an acid anhydride, and an inorganic resin.
In a one-pack type epoxy resin composition containing
As an anti-settling agent for machine filler, a general formula, (In the formula, R1Is a higher alkyl group or alkenyl group, R2,
R3Is a lower alkyl group)
Containing a combination of acid derivative and aluminum hydroxide
A liquid epoxy resin composition comprising:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09678193A JP3458160B2 (en) | 1993-03-31 | 1993-03-31 | Liquid epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09678193A JP3458160B2 (en) | 1993-03-31 | 1993-03-31 | Liquid epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06287409A true JPH06287409A (en) | 1994-10-11 |
| JP3458160B2 JP3458160B2 (en) | 2003-10-20 |
Family
ID=14174184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09678193A Expired - Fee Related JP3458160B2 (en) | 1993-03-31 | 1993-03-31 | Liquid epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3458160B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000915A1 (en) * | 1995-06-20 | 1997-01-09 | Ciba Specialty Chemicals Holding Inc. | Curable compositions |
| JPH115827A (en) * | 1997-06-18 | 1999-01-12 | Hitachi Chem Co Ltd | Epoxy resin composition and production of electric equipment |
| JP2011079973A (en) * | 2009-10-07 | 2011-04-21 | Hitachi Chem Co Ltd | Method for producing and method for adjusting liquid resin composition for sealing and method for sealing semiconductor device and semiconductor element using the same |
-
1993
- 1993-03-31 JP JP09678193A patent/JP3458160B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000915A1 (en) * | 1995-06-20 | 1997-01-09 | Ciba Specialty Chemicals Holding Inc. | Curable compositions |
| JPH115827A (en) * | 1997-06-18 | 1999-01-12 | Hitachi Chem Co Ltd | Epoxy resin composition and production of electric equipment |
| JP2011079973A (en) * | 2009-10-07 | 2011-04-21 | Hitachi Chem Co Ltd | Method for producing and method for adjusting liquid resin composition for sealing and method for sealing semiconductor device and semiconductor element using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3458160B2 (en) | 2003-10-20 |
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| LAPS | Cancellation because of no payment of annual fees |