JP4290519B2 - インクジェット用カチオン硬化性組成物とその硬化物、及びそれを用いたプリント配線板 - Google Patents
インクジェット用カチオン硬化性組成物とその硬化物、及びそれを用いたプリント配線板 Download PDFInfo
- Publication number
- JP4290519B2 JP4290519B2 JP2003353717A JP2003353717A JP4290519B2 JP 4290519 B2 JP4290519 B2 JP 4290519B2 JP 2003353717 A JP2003353717 A JP 2003353717A JP 2003353717 A JP2003353717 A JP 2003353717A JP 4290519 B2 JP4290519 B2 JP 4290519B2
- Authority
- JP
- Japan
- Prior art keywords
- cationic
- epoxy resin
- polymerizable monomer
- curable composition
- inkjet
- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 33
- 125000002091 cationic group Chemical group 0.000 claims description 50
- 239000000178 monomer Substances 0.000 claims description 48
- 229910000679 solder Inorganic materials 0.000 claims description 29
- -1 oxetane compound Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 9
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000005476 soldering Methods 0.000 claims description 2
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- 239000000126 substance Substances 0.000 description 30
- 239000011248 coating agent Substances 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
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- 238000001723 curing Methods 0.000 description 12
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- 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 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
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- 239000003999 initiator Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
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- KATAXDCYPGGJNJ-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethoxy)propan-2-ol Chemical compound C1OC1COCC(O)COCC1CO1 KATAXDCYPGGJNJ-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- FPSURBCYSCOZSE-UHFFFAOYSA-N 1-ethenoxybutan-1-ol Chemical compound CCCC(O)OC=C FPSURBCYSCOZSE-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 2
- FDZMLNCJBYFJBH-UHFFFAOYSA-N 2-[(2,3-dibromophenoxy)methyl]oxirane Chemical compound BrC1=CC=CC(OCC2OC2)=C1Br FDZMLNCJBYFJBH-UHFFFAOYSA-N 0.000 description 2
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 2
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 2
- DCOXQQBTTNZJBI-UHFFFAOYSA-N 3-ethyl-3-[[4-[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]phenyl]methoxymethyl]oxetane Chemical group C=1C=C(C=2C=CC(COCC3(CC)COC3)=CC=2)C=CC=1COCC1(CC)COC1 DCOXQQBTTNZJBI-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Description
さらに本発明の目的は、かかるカチオン硬化性組成物を用いて直接描画された耐熱性のあるソルダーレジストパターンを形成したプリント配線板を提供することにある。
ここでいう粘度は、JIS K2283に従って常温(25℃)で測定した粘度をいう。前記したように、インクジェット方式の場合、インクの粘度は塗布時の温度において約20mPa・s以下であることが必要であるが、常温で150mPa・s以下であれば、加温することによって塗布時にはこの条件を満足することができる。なお、本発明のインクジェット用カチオン硬化性組成物は、組成物全体として25℃での粘度が150mPa・s以下であればよい。
まず、カチオン重合性モノマー(A)としては、エポキシ化合物、オキセタン化合物、ビニルエーテル化合物、脂環式エポキシ樹脂等が挙げられ、単独で又は2種以上を組み合わせて用いることができる。但し、少なくとも芳香環を有するカチオン重合性モノマーと水酸基を有するカチオン重合性モノマーの2種を含む。
また、カチオン重合性モノマーとしてエポキシ化合物のみを用いた場合には、粘度が高くなり易く、また活性エネルギー線照射による硬化の際に充分な硬化度が得難く、一方、オキセタン化合物のみを用いた場合には活性エネルギー線照射による硬化開始反応が遅く、照射量を多くする必要があるため、これらを混合して用いることにより、活性エネルギー線照射による硬化が速やかに進行するようにすることが好ましい。
光カチオン重合開始剤としては、例えばジアゾニウム塩、ヨードニウム塩、ブロモニウム塩、クロロニウム塩、スルホニウム塩、セレノニウム塩、ピリリウム塩、チアピリリウム塩、ピリジニウム塩等のオニウム塩;トリス(トリハロメチル)−s−トリアジン及びその誘導体等のハロゲン化化合物;スルホン酸の2−ニトロベンジルエステル;イミノスルホナート;1−オキソ−2−ジアゾナフトキノン−4−スルホナート誘導体;N−ヒドロキシイミド=スルホナート;トリ(メタンスルホニルオキシ)ベンゼン誘導体;ビススルホニルジアゾメタン類;スルホニルカルボニルアルカン類;スルホニルカルボニルジアゾメタン類;ジスルホン化合物等が挙げられる。
市販されているものとしては、サイラキュアUVI−6970、UVI−6974、UVI−6990、UVI−6950(以上、UCC社製の商品名)、イルガキュア261(チバ・スペシャリティ・ケミカルズ社製の商品名)、SP−150、SP−152、SP−170(以上、旭電化工業(株)製の商品名)、CG−24−61(チバ・スペシャリティ・ケミカルズ社製の商品名)、DAICAT II(ダイセル化学工業(株)製の商品名)、UVAC1591(ダイセル・ユーシービー(株)製の商品名)、CI−2734、CI−2855、CI−2823、CI−2758(以上、日本曹達(株)製の商品名)、PI−2074(ローヌプーラン(株)製の商品名)、FFC509(3M(株)製の商品名)、ロードシル フォトイニシエーター2074(ローディア(株)製の商品名)、BBI−102、BBI−101(ミドリ化学(株)製の商品名)、CD−1012(サートマー(株)社製の商品名)等が挙げられる。
表1に示す配合成分を、表2に示す配合割合で混合し、ディスパーマットCA−40及びMilling System(Getmann社製)で20分間分散させ、1.0μmのフィルターにて濾過を行ない、インクジェット用カチオン硬化性組成物を得た。
<インクジェットプリンターによる描画条件>:
膜厚:20μm
装置:ピエゾ方式インクジェットプリンターを使用(ヘッド温度:50℃)
<UV硬化の条件>:
露光量:1000mJ/cm2
<熱硬化の条件>:
150℃×30分
<粘度>
JIS K−2283の測定法に準拠して測定した。なお、測定温度は25℃である。
JIS K−5400に準拠して測定した。
硬化塗膜をアセトンに30分間浸漬した後の塗膜状態を目視にて観察し、以下の基準で評価した。
○:全く変化が認められないもの。
△:ほんの僅か変化(白化)しているもの。
×:塗膜の膨潤又は剥離が認められるもの。
硬化塗膜を5wt.%の硫酸水溶液に10分間浸漬した後の塗膜状態を観察し、以下の基準で評価した。
○:全く変化が認められないもの。
△:ほんの僅か変化(白化)しているもの。
×:塗膜の膨潤又は剥離が認められるもの。
硬化塗膜を、JIS C−6481の方法に準拠し、260℃のはんだ槽に10秒間浸漬後、セロハン粘着テープによるピーリング試験を行なった後の塗膜状態を目視にて観察し、問題ない場合は同様の試験を2回以上繰り返した。
5回:5回行なっても塗膜に変化がないもの。
3回:3回行なっても塗膜に変化がないもの。
2回:2回行なっても塗膜に変化がないもの。
×:1回でも塗膜が剥離したもの。
市販の無電解ニッケルめっき浴及び無電解金めっき浴を用いて、ニッケル0.5μm、金0.03μmの条件でめっきを行ない、硬化塗膜表面状態の観察を行なった。判定基準は以下の通りである。
◎:全く変化のないもの。
○:ほんの僅かに変化があるもの。
△:変化があるもの。
×:顕著に白化若しくは曇りが生じたもの。
Claims (5)
- (A)カチオン重合性モノマー及び(B)カチオン重合開始剤を含有し、粘度が25℃で150mPa・s以下であり、且つ、上記カチオン重合性モノマー(A)として、少なくとも芳香環を有するカチオン重合性モノマー(A−1)と水酸基を有するカチオン重合性モノマー(A−2)の2種を含むことを特徴とする、硬化物が耐熱性のあるプリント配線板のソルダーレジスト形成用又はマーキング用のインクジェット用カチオン硬化性組成物。
- 前記芳香環を有するカチオン重合性モノマー(A−1)は、芳香環を有するオキセタン化合物であることを特徴とする請求項1に記載のインクジェット用カチオン硬化性組成物。
- 前記水酸基を有するカチオン重合性モノマー(A−2)は、水酸基を有するビニルエーテル化合物及び/又はオキセタンアルコールであることを特徴とする請求項1又は2に記載のインクジェット用カチオン硬化性組成物。
- 前記請求項1乃至3のいずれか一項に記載のインクジェット用カチオン硬化性組成物を用い、インクジェット方式にて塗布すると同時に又は塗布した後に、活性エネルギー線照射、もしくは加熱、又は活性エネルギー線照射後に加熱もしくは再度活性エネルギー線を照射して硬化させることにより、所定のソルダーレジストパターンに形成された硬化物。
- 前記請求項1乃至3のいずれか一項に記載のインクジェット用カチオン硬化性組成物を用い、インクジェットプリンターで直接描画されたソルダーレジストパターンを有するプリント配線板。
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JP4896474B2 (ja) * | 2005-09-15 | 2012-03-14 | 新日鐵化学株式会社 | 低誘電率・低吸水率プリント回路用積層板及びその材料 |
KR100984605B1 (ko) * | 2006-02-27 | 2010-09-30 | 쇼와 덴코 가부시키가이샤 | 저염소 다관능 지방족 글리시딜에테르 화합물을 포함하는 열경화성 수지 조성물, 상기 조성물의 경화물 및 그의 용도 |
EP1999177B1 (en) * | 2006-03-29 | 2016-05-11 | Henkel AG & Co. KGaA | Radiation-or thermally-curable barrier sealants |
JP5617201B2 (ja) * | 2009-07-23 | 2014-11-05 | Jnc株式会社 | 光硬化性インクジェット用インク |
JP2012052074A (ja) * | 2010-09-03 | 2012-03-15 | Sekisui Chem Co Ltd | インクジェット用硬化組成物及びプリント配線基板の製造方法 |
JP5947817B2 (ja) * | 2011-02-14 | 2016-07-06 | セリコル リミテッド | インクジェット印刷方法 |
JP5862901B2 (ja) * | 2013-12-13 | 2016-02-16 | Jnc株式会社 | 光硬化性インクジェット用インク |
US9540529B2 (en) * | 2015-01-13 | 2017-01-10 | Xerox Corporation | Solder mask compositions for aerosol jet printing |
US11214699B2 (en) | 2017-10-20 | 2022-01-04 | Lg Chem, Ltd. | Ink composition |
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