JP7081486B2 - 光硬化性樹脂組成物、インキ及び塗料 - Google Patents
光硬化性樹脂組成物、インキ及び塗料 Download PDFInfo
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- JP7081486B2 JP7081486B2 JP2018535588A JP2018535588A JP7081486B2 JP 7081486 B2 JP7081486 B2 JP 7081486B2 JP 2018535588 A JP2018535588 A JP 2018535588A JP 2018535588 A JP2018535588 A JP 2018535588A JP 7081486 B2 JP7081486 B2 JP 7081486B2
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
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- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
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- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
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- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000003756 stirring Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
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Description
下記一般式[I]で表される化合物を重合して得られる重合体(A)を含有することを特徴とする。
また、この光硬化性樹脂組成物は特にPP(ポリプロピレン)樹脂に対する密着性に優れるため、従来のジアリルフタレート樹脂を用いた組成物では密着性を高くすることが困難であったPP樹脂用のインキ、塗料の成分として適している。
このインキは、プラスチック基材に印刷するためのインキとして適しており、特にPP樹脂製のシート、フィルム等の基材に印刷するためのインキとして適している。
この塗料は、プラスチック基材に描画するための塗料として適しており、特にPP樹脂製のシート、フィルム等の基材に描画するための塗料として適している。
また、本発明の塗料はオーバープリントワニスであることが好ましい。
本発明の光硬化性樹脂組成物は、下記一般式[I]で表される化合物を重合して得られる重合体(A)を含有することを特徴とする。
本発明において、重合体(A)を含有することにより、合成高分子の基材、特にプラスチック基材に対する密着性に優れる理由については定かではないが、以下のように推測される。
下記一般式[I]で表される化合物を重合して得られる重合体(A)では、イソシアヌレート環に基づく構造(下記一般式[I]中の環構造(イソシアネートの三量体))が連続して存在しており、連続して存在するイソシアヌレート環に基づく構造により、合成高分子の基材、特にプラスチック基材に対する密着性に優れるものと推測される。
本明細書において、重合体(A)の重量平均分子量(Mw)、数平均分子量(Mn)は実施例に記載の方法により測定される値である。
本発明の光硬化性樹脂組成物は、光照射により硬化可能であるエチレン性不飽和化合物(B)を含有することが好ましい。エチレン性不飽和化合物(B)は、炭素-炭素二重結合を1~20個有することが好ましく、1~10個有することがより好ましく、2~6個有することがさらに好ましい。エチレン性不飽和化合物(B)としては、(メタ)アクリル酸エステル化合物、(メタ)アリル化合物及びビニル化合物等が挙げられる。また、エチレン性不飽和化合物は2種以上の化合物の混合物を用いることも可能である。
ビニル化合物としては、スチレン、ジビニルベンゼン、N-ビニルピロリドン、酢酸ビニル等を例示することができる。
また、本発明の光硬化性樹脂組成物中における重合体(A)とエチレン性不飽和化合物(B)の比率(重合体:エチレン性不飽和化合物)は、重量比で、5:95~95:5の範囲であればよく、10:90~90:10の範囲であることが好ましく、10:90~70:30の範囲であることがより好ましく、10:90~50:50の範囲であることがさらに好ましい。上記範囲内であれば、プラスチック基材への充分な密着性が得られやすい。
本発明の光硬化性樹脂組成物は、重合開始剤を含んでいてもよく、特に光重合開始剤を含有することが好ましい。光硬化性樹脂組成物に含有される光重合開始剤としては、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、等のアセトフェノン系、ベンゾイン、ベンゾインエチルエ-テル等のベンゾイン系、ベンゾフェノン等のベンゾフェノン系、アシルフォスフィンオキサイド等のリン系、チオキサントン等のイオウ系、ベンジル、9,10-フェナンスレンキノン等のベンジル系が挙げられる。
光開始助剤の量は、光硬化性樹脂組成物全体に対して、0.1~5重量%の範囲であることが好ましく、0.5~3重量%の範囲がより好ましい。
着色剤の量は、光硬化性樹脂組成物全体に対して、1~50重量%の範囲であることが好ましく、1~45重量%の範囲がより好ましい。
本発明の光硬化性樹脂組成物を含むインキは本発明のインキであり、本発明の光硬化性樹脂組成物を含む塗料は本発明の塗料である。また、本発明の塗料はオーバープリントワニスであることが好ましい。
また、オーバープリントワニスの作成は、顔料を使用しない以外は、インキと同様の手順により行える。
以下、実施例を挙げて、本発明をより具体的に説明するが、本発明はこれらの実施例に限定されるものではない。
カラム:ShodexLF-804×2本を直列に接続
流速:1.0mL/min
温度:40℃
検出:RID-20A
試料:試料30mgをテトラヒドロフラン3mLに溶解させ測定用のサンプルとした。
3Lのセパラブルフラスコにトリアリルイソシアヌレート600gを加え、15gのベンゾイルパーオキサイドを加えて80℃で加熱攪拌した。1時間反応させた後、室温(25℃)まで冷却した。冷却後、フラスコにメタノールを加え、重合体を沈殿させた。得られた重合体を40℃で16時間減圧乾燥した(収量:73g、収率:12%、Mw=53,000、Mw/Mn=3.3)。得られた重合体を重合体1とし、実施例1、4~6に用いた。
製造例1の反応時間を1.25時間とした以外は同様の方法で合成を行った。(収量:84g、収率:14%、Mw=94,000、Mw/Mn=5.3)。得られた重合体を重合体2とし、実施例2に用いた。
製造例1の反応時間を1.5時間とした以外は同様の方法で合成を行った。(収量:94g、収率:16%、Mw=126,000、Mw/Mn=6.9)。得られた重合体を重合体3とし、実施例3に用いた。
下記表1に記載の各組成の光硬化性樹脂組成物を調製し、光硬化性樹脂組成物の特性を評価した。
また、表1に示す組成量は重量部での表記である。
DAP樹脂:(株)大阪ソーダ製 ダイソーダップA(ジアリルフタレート樹脂)
トリアリルイソシアヌレート(モノマー)
DTMPTA:サートマー(株)製 SR355 ジトリメチロールプロパンテトラアクリレート
Irgacure907:BASF ジャパン(株)製 2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン
Irganox1076:BASFジャパン(株)製 オクタデシル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート
各製造例で得られた各重合体1~3、DAP樹脂、トリアリルイソシアヌレート(モノマー)、エチレン性化合物、及び重合開始剤を表1に記載した各組成量を添加し、加熱混合して光硬化性樹脂組成物を調製した。各組成物を室温(25℃)に冷却後、一晩経過したものの外観が透明であるかで溶解性を確認した。冷却後も外観が透明であったものを〇、白濁したものを×とした。結果は表2に示す。
調製した光硬化性樹脂組成物を、プラスチックフィルム(ポリプロピレン基材:龍田化学株式会社製 無延伸高透明PPシート 品名:ハイピークリスタル ST-500 厚み0.3mm)にRIテスターを用いてコートし、出力120W/cmのメタルハライドランプ(ランプ距離11cm、コンベアスピード50m/min)で硬化させた。なお、UV硬化装置はアイグラフィックス株式会社製コンベア型紫外線硬化装置を用いた。塗膜を指で触り、面に指紋が付かない状態(タックフリー)になるまで複数回通過させ、その回数で乾燥性を評価した。評価結果を表2に示す。
調製した光硬化性樹脂組成物を、乾燥性試験と同様の方法でプラスチックフィルムにコートし、硬化させた。得られた塗膜に、ニチバン社製18mm幅のセロテープ(登録商標、品番:LP-18、粘着力:4.01N/10mm)を貼り付け、親指で10回強く擦った後、セロテープ(登録商標)を真上にゆっくりと引き離した。完全に剥離しなかったものを○、完全に剥離したものを×とした。評価結果を表2に示す。
Claims (5)
- 一般式[I]で表される化合物を重合して得られる重合体(A)、エチレン性不飽和化合物(B)を含有し、
一般式[I]で表される化合物に基づく単量体単位の含有量が、重合体(A)100重量%中、100重量%であり、
重合体(A)の重量平均分子量が10,000~150,000であり、
重合体(A)の含有量が、光硬化性樹脂組成物全量に対して、1~50重量%であり、
エチレン性不飽和化合物(B)の含有量が、重合体(A)100重量部に対して、50~1200重量部であるプラスチック基材用光硬化性樹脂組成物。
- 更に、光重合開始剤を含有し、プラスチック基材がポリプロピレン又はポリエチレンテレフタレートである請求項1に記載のプラスチック基材用光硬化性樹脂組成物。
- 請求項1又は2に記載のプラスチック基材用光硬化性樹脂組成物を含むことを特徴とするインキ。
- 請求項1又は2に記載のプラスチック基材用光硬化性樹脂組成物を含むことを特徴とする塗料。
- オーバープリントワニスである請求項4に記載の塗料。
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JP2002099081A (ja) | 2000-09-21 | 2002-04-05 | Tamura Kaken Co Ltd | 感光性樹脂組成物及びプリント配線板 |
JP2012144605A (ja) | 2011-01-11 | 2012-08-02 | Daiso Co Ltd | 光硬化性樹脂組成物とその用途 |
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US11149157B2 (en) | 2021-10-19 |
JPWO2018037912A1 (ja) | 2019-06-20 |
CN109641985B (zh) | 2022-04-22 |
TW201809171A (zh) | 2018-03-16 |
TWI808944B (zh) | 2023-07-21 |
CN109641985A (zh) | 2019-04-16 |
US20190203061A1 (en) | 2019-07-04 |
KR20190043530A (ko) | 2019-04-26 |
WO2018037912A1 (ja) | 2018-03-01 |
EP3502150A4 (en) | 2020-01-22 |
EP3502150A1 (en) | 2019-06-26 |
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