JP6069300B2 - 光硬化性熱硬化性組成物、その硬化物の製造方法、硬化物およびこれを有するプリント配線板 - Google Patents
光硬化性熱硬化性組成物、その硬化物の製造方法、硬化物およびこれを有するプリント配線板 Download PDFInfo
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- JP6069300B2 JP6069300B2 JP2014507876A JP2014507876A JP6069300B2 JP 6069300 B2 JP6069300 B2 JP 6069300B2 JP 2014507876 A JP2014507876 A JP 2014507876A JP 2014507876 A JP2014507876 A JP 2014507876A JP 6069300 B2 JP6069300 B2 JP 6069300B2
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- acrylate
- isocyanate
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- 238000004040 coloring Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 52
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 45
- -1 OH or NH 2 Chemical class 0.000 description 36
- 239000000758 substrate Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 23
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 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
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C09D11/10—Printing inks based on artificial resins
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- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
- H05K2203/01—Tools for processing; Objects used during processing
- H05K2203/0104—Tools for processing; Objects used during processing for patterning or coating
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
本発明では、(メタ)アクリロイル基含有モノマーは、1分子中に1個以上の(メタ)アクリロイル基を有する。また、(メタ)アクリロイル基含有モノマーはイソシアネートと反応しうる官能基を持たない化合物を使用できる。
本発明ではイソシアネート化合物は、公知のブロック化剤(封止剤)でブロックされたブロックイソシアネートを使用する。ブロックイソシアネートとして、ブロックを有する脂肪族/脂環式イソシアネート、および芳香族イソシアネートを使用することができる。
脂肪族/脂環式イソシアネート化合物としては、例えば、1,6−ヘキサメチレンジイソシアネート(HDIまたはHMDI)、イソホロンジイソシアネート(IPDI)、メチルシクロヘキサン2,4−(2,6)−ジイソシアネート(水素化TDI)、4,4′−メチレンビス(シクロヘキシルイソシアネート)(水素化MDI)、1,3−(イソシアネートメチル)シクロヘキサン(水素化XDI)、ノルボルネンジイソシアネート(NDI)、リジンジイソシアネート(LDI)、トリメチルヘキサメチレンジイソシアネート(TMDI)、ダイマー酸ジイソシアネート(DDI)、N,N’,N’’−トリス(6−イソシアネート、ヘキサメチレン)ビウレットを用いることができる。
ブロック化剤としては、例えば、エタノール、n−プロパノール、イソプロパノール、t−ブタノール、イソブタノールなどのアルコール類、フェノール、クロルフェノール、クレゾール、キシレノール、p−ニトロフェノールなどのフェノール類、p−t−ブチルフェノール、p−sec−ブチルフェノール、p−sec−アミノフェノール、p−オクチルフェノール、p−ノニルフェノールなどのアルキルフェノール類、3−ヒドロキシピリジン、8−ヒドロキシキノリン、8−ヒドロキシキナルジンなどの塩基性窒素含有化合物、マロン酸ジエチル、アセト酢酸エチル、アセチルアセトンなどの活性メチレン化合物、アセトアミド、アクリルアミド、アセトアニリドなどの酸アミド類、コハク酸イミド、マレイン酸イミドなどの酸イミド類、2−エチルイミダゾール、2−エチル−4−メチルイミダゾールなどのイミダゾール類、ピラゾール、3−メチルピラゾール、3,5−ジメチルピラゾール等のピラゾール類、2−ピロリドン、ε−カプロラクタムなどのラクタム類、アセトキシム、メチルエチルケトンオキシム、シクロヘキサノンオキシム、アセトアルドキシムなどのケトンまたはアルデヒドのオキシム類、エチレンイミン、重亜硫酸塩などがあげられる。
光重合開始剤としては、エネルギー線の照射により、(メタ)アクリレートを重合させることが可能なものであれば、特に制限はなく、ラジカル重合開始剤が使用できる。
本発明の光硬化性熱硬化性樹脂組成物には、必要に応じて消泡・レベリング剤、チクソトロピー付与剤・増粘剤、カップリング剤、分散剤、難燃剤等の添加剤を含有させることができる。
140℃〜170℃の温度範囲で加熱することによりアクリロイル基のほぼすべての二重結合が開き、(メタ)アクリロイル基含有モノマーが架橋した状態となる。
I.組成物の調整
表1に示す割合で各成分を配合し、これをディゾルバーで攪拌した。実施例7および8については、更にビーズミルにて分散を行ない、次いで1μmのディスクフィルターでろ過を行った。これにより、本発明の組成物および比較組成物を得た。
II.特性試験
上記各組成物について以下に示す特性試験を行った。その結果を表1に示す。
富士フィルム製インクジェットプリンターDimatix Materials Printer DMP−2831を用い、プリントヘッドの横にスポットUV照射機の照射部を粘着テープで固定した。これにより、塗布と同時にUV照射が可能なインクジェットプリンターを構成した。
○:ラインにかすれやよれがなく正しく描画できており、指触でもべたつきがない。
×:ラインにかすれやよれがなく正しく描画できているが、指触では若干のべたつきがある。
富士フィルム製インクジェットプリンターDimatix Materials Printer DMP−2831を用い、プリント配線板用銅張積層板(FR−4、150mm×95mm×1.6mm)に、上記各組成物で10mm×20mmの長方形のパターンを膜厚が15μmで印刷した。
○:ほとんどはがれが見られない。
×:セロテープ(登録商標)に大きく転写するはがれがある。
上記各組成物について、上記密着性試験に記載した方法と同様の方法で各試験片を作製した。得られた試験片の状態を観察した(未処理状態)。
○:未処理状態に対して、薬品試験後も、ピーリング後も、いずれも塗膜の状態に全く変化がない。
△:未処理状態に対して、薬品試験後では変化が無いが、ピーリング後では若干のはがれが観察された。
×:未処理状態に対して、薬品試験後に塗膜に浮き、はがれがが観察され、或いは、ピーリング後にセロテープ(登録商標)に大きく転写するはがれが観察された。
上記各組成物について、上記密着性試験に記載した方法と同様の方法で各試験片を作製した。各サンプルにロジン系フラックス(サンワ化学社製SF−270)を塗布して、260℃のはんだ槽に10秒間浸漬した。各サンプルをはんだ層から取り出して自然冷却した後、プロピレングリコールモノメチルエーテルアセテートで洗浄し、乾燥した。この試験を3回繰返した後、各試験片の塗膜の状態を目視評価後、セロテープ(登録商標)でピーリングを行い、以下のとおり評価した。
○:塗膜の状態に全く変化がない。
△:目視では変化が無いが、セロテープ(登録商標)ピーリングでは若干のはがれがある。
×:塗膜に浮き、はがれがある。または、セロテープ(登録商標)に大きく転写するはがれがある。
IPC B−25テストパターンのクシ型電極Bクーポン(基板)に対し、上記各組成物で10mm×20mmの長方形のパターンを膜厚40μmで印刷した。
印刷直後(約0.5秒後)の積層板に対して、高圧水銀灯を用いて300mJ/cm2の積算光量でUV照射した。次いで、このUV照射済の積層板を熱風循環式乾燥炉にて150℃30分加熱し、上記パターンを加熱硬化させ、試験片とした。
得られた試験片に、DC500Vのバイアスを印加し、絶縁抵抗値を測定した。以下のとおり評価した。
○:絶縁抵抗値≧100GΩ
×:絶縁抵抗値<100GΩ
各組成物について、粘度を測定した(初期粘度)。
その後、各組成物を密閉した容器中で50℃にて2週間保存し、再度粘度を測定し、増粘率(%)を求めた。
増粘率を以下のように評価した。
○: 増粘率10%以内
△: 10%以上20%未満
×: 20%以上または固化して測定不能
<7.保存安定性2>
各組成物について、粘度を測定した(初期粘度)。
増粘率を以下のように評価した。
○: 増粘率1%以内
△: 1%以上10%未満
×: 10%以上
プリント配線板用銅張積層板(FR−4、150mm×95mm×1.6mm)に対し、太陽インキ製造社製ソルダーレジストPSR−4000 G24を、乾燥塗膜が20μmになるようにスクリーン印刷にてベタ印刷した。
目視で下地とのコントラストについて以下の基準により評価した。
○:印刷箇所と試験用基板とのコントラストが良く、視認性に優れる。
△:印刷箇所と試験用基板とのコントラストが明確ではなく、視認性に劣る。
表中の各材料の配合量は質量部を単位とする。
光重合開始剤2:BASFジャパン社製 イルガキュア127
エポキシ樹脂2: 1,6−ヘキサンジオールジグリシジルエーテル ナガセケムテックス社製 EX−212
エポキシ硬化剤1:2 - エチル - 4 - メチルイミダゾール 四国化成工業社製 2E4MZ
エポキシ硬化剤2:2 - フェニル - 4,5 - ジヒドロキシメチルイミダゾール 四国化成工業社製 2PHZ−PW
レベリング剤:ビックケミー・ジャパン社製 BYK-307
分散剤:ビックケミー・ジャパン社製 DISPERBYK-111
酸化チタン:石原産業社製 CR−95
本発明の組成物は、いずれも即時硬化塗布性、密着性、耐薬品性、耐熱性、絶縁性、保存安定性に優れている。これらの特性を必要とするプリント配線板への適用には極めてに好ましいといえる。
[DSCデータの測定]
アクリレート1のトリメチロールプロパンおよび比較例9の組成物について、セイコーインスツル社製EXSTARを用い、示差走査熱量測定(DSC)を行った。得られたDSC曲線を図1に示す。
比較例9の組成物について、パーキンエルマージャパン社製Spectrum100を用い、赤外分光法(IR Spectroscopy)による吸光度(absorption)を測定した。なお、マクロATRユニットとして、smiths Dura Sampl IRIIを用いた。
図1と図2に示した測定結果を併せて考察すると、イソシアネートとアクリレートが共存している状態で加熱することにより、イソシアネートの3量化が起こり、その3量化の反応に伴い、アクリレートの重合が生じていると言える。
Claims (5)
- (メタ)アクリロイル基含有モノマーと、
トリアジン骨格を持つブロックされた多官能イソシアネートと、
光重合開始剤と、
を含み、インクジェット法による印刷に使用されることを特徴とする光硬化性熱硬化性組成物。 - 前記(メタ)アクリロイル基含有モノマーは、多官能(メタ)アクリロイル基含有モノマーと、単官能(メタ)アクリロイル基含有モノマーと、をそれぞれ少なくとも一種以上含むことを特徴とする請求項1に記載の光硬化性熱硬化性組成物。
- さらに、着色顔料を含むことを特徴とする請求項1または2のいずれか1項に記載の光硬化性熱硬化性組成物。
- 請求項1〜3のいずれか1項に記載の光硬化性熱硬化性組成物の硬化物。
- 請求項4に記載の硬化物を有することを特徴とするプリント配線板。
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