JP2006008798A - エポキシ樹脂の製造方法 - Google Patents
エポキシ樹脂の製造方法 Download PDFInfo
- Publication number
- JP2006008798A JP2006008798A JP2004186333A JP2004186333A JP2006008798A JP 2006008798 A JP2006008798 A JP 2006008798A JP 2004186333 A JP2004186333 A JP 2004186333A JP 2004186333 A JP2004186333 A JP 2004186333A JP 2006008798 A JP2006008798 A JP 2006008798A
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- Prior art keywords
- epoxy resin
- reaction
- resin composition
- phenol
- weight
- 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
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 128
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
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- 239000003054 catalyst Substances 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006482 condensation reaction Methods 0.000 claims abstract description 13
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- 150000002989 phenols Chemical class 0.000 claims description 33
- 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 claims description 26
- 238000010438 heat treatment Methods 0.000 claims description 22
- 230000002378 acidificating effect Effects 0.000 claims description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
- 238000006266 etherification reaction Methods 0.000 claims description 12
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- 229930185605 Bisphenol Natural products 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 45
- 238000006243 chemical reaction Methods 0.000 abstract description 22
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- 230000003472 neutralizing effect Effects 0.000 abstract description 5
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract description 2
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- 239000000463 material Substances 0.000 description 21
- 239000011342 resin composition Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- -1 resists Substances 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 17
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- 238000000465 moulding Methods 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- 238000011109 contamination Methods 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
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- 235000013824 polyphenols Nutrition 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000004593 Epoxy Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000004760 aramid Substances 0.000 description 4
- 229920003235 aromatic polyamide Polymers 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 125000002723 alicyclic group Chemical group 0.000 description 3
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
【解決手段】 2価フェノール類(x1)とアルデヒド類(x2)とを酸性触媒(I)の存在下、120℃以下で縮合反応させて多価フェノール類(a)を得た後、中和及び/又は水洗し、引き続きエピハロヒドリン(x3)を加え、塩基性触媒(II)の存在下にグリシジルエーテル化反応させてエポキシ樹脂(A)を得ることを特徴とするエポキシ樹脂の製造方法。
【選択図】 なし
Description
[1]色数:エポキシ樹脂5.0gをアセトン5.0gに溶解させたのち、JIS K6901記載のハーゼン色数測定法に準拠した。
[2]エポキシ当量:JIS K−7236に準じた方法で測定した。
[3]収率:2価フェノール類(x1)の使用量から算出した理論収量に対する実収量の重量%
[4]ガラス転移温度:DMA法により測定した。
多価フェノール類(a)の合成
加熱装置と攪拌装置とコンデンサと温度計および下部に分液コックが装着された反応装置に窒素ガスを流しながら、表1に示す量のビスフェノールAとビスフェノールA1モルに対し0.62モルの41重量%ホルムアルデヒド水溶液およびビスフェノールA100重量部に対し5重量部のイソプロピルアルコールを添加した。
多価フェノール類(a)の合成後、ひきつづき反応装置に多価フェノール類(a)の水酸基1モルに対して3.5モルのエピクロルヒドリンおよびエピクロルヒドリン100重量部に対し30重量部のイソプロピルアルコールを添加し、溶解させながら40℃まで降温した。
多価フェノール類(a’)の合成
表2に示す量のビスフェノールAを用いて、実施例1〜2と同様にして多価フェノール類を合成した後、170℃まで昇温しメタノールや水を蒸留にて留去し、溶融状態で下部の分液コックより抜き出し、次いで室温で冷却固化させ、多価フェノール類(a’)を得た。
加熱装置と攪拌装置とコンデンサと温度計および下部に分液コックが装着された反応装置に窒素ガスを流しながら、表2に示す量の多価フェノール類(a’)とエピクロルヒドリンおよびエピクロルヒドリン100重量部に対し30重量部のイソプロピルアルコールを添加しながら40℃まで降温した。次いで実施例1〜2と同様の操作においてエポキシ樹脂(A’)を得た。
表3、4に記載した配合に従って、エポキシ樹脂、硬化剤、硬化促進剤、無機充填材及び離型剤を混合した後、加熱ロールを用いて、温度85℃で5分間混練し、次いで冷却した。その後、粉砕して封止樹脂を得た。尚、硬化剤としてはフェノール樹脂[大日本インキ化学工業製、フェノライトTD−2131]を、硬化促進剤としてはトリフェニルホスフィン[北興化学工業株式会社製]を、無機充填剤としては結晶シリカ[龍森社製、商品名3K]を、離型剤としては天然カルナバワックスを使用した。
Claims (7)
- 2価フェノール類(x1)とアルデヒド類(x2)とを酸性触媒(I)の存在下120℃以下で縮合反応させて多価フェノール類(a)を得た後、中和及び/又は水洗し、引き続きエピハロヒドリン(x3)を加え塩基性触媒(II)の存在下にグリシジルエーテル化反応させてエポキシ樹脂(A)を得ることを特徴とするエポキシ樹脂の製造方法。
- 多価フェノール類(a)を得た後、120℃以上の加熱蒸留を行うことなく、グリシジルエーテル化反応を行う請求項1記載のエポキシ樹脂の製造方法。
- 酸性触媒(I)がリン酸である請求項1記載のエポキシ樹脂の製造方法。
- 塩基性触媒(II)がアルカリ金属水酸化物である請求項1記載のエポキシ樹脂の製造方法。
- 2価フェノール類(x1)がビスフェノール類である請求項1記載のエポキシ樹脂の製造方法。
- ビスフェノール類がビスフェノールAである請求項5記載のエポキシ樹脂の製造方法。
- アルデヒド類(x2)がホルムアルデヒドである請求項1〜6の何れか1項記載のエポキシ樹脂の製造方法。
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US8777392B2 (en) | 2009-04-23 | 2014-07-15 | Konica Minolta Business Technologies, Inc. | Inkjet ink and inkjet recording method |
JP2017002128A (ja) * | 2015-06-05 | 2017-01-05 | Dic株式会社 | (メタ)アクリレート樹脂及びレジスト部材 |
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JP2017002128A (ja) * | 2015-06-05 | 2017-01-05 | Dic株式会社 | (メタ)アクリレート樹脂及びレジスト部材 |
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