JPWO2018105442A1 - 活性エネルギー線硬化型樹脂組成物及び積層フィルム - Google Patents
活性エネルギー線硬化型樹脂組成物及び積層フィルム Download PDFInfo
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- JPWO2018105442A1 JPWO2018105442A1 JP2018554934A JP2018554934A JPWO2018105442A1 JP WO2018105442 A1 JPWO2018105442 A1 JP WO2018105442A1 JP 2018554934 A JP2018554934 A JP 2018554934A JP 2018554934 A JP2018554934 A JP 2018554934A JP WO2018105442 A1 JPWO2018105442 A1 JP WO2018105442A1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LVOICKNPHXSSQM-UHFFFAOYSA-N prop-2-en-1-one Chemical compound C=C[C]=O LVOICKNPHXSSQM-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical compound [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
Abstract
Description
粒子径測定装置:大塚電子株式会社製「ELSZ−2」
粒子径測定サンプル:活性エネルギー線硬化型樹脂組成物を不揮発分1質量%のメチルイソブチルケトン溶液としたもの。
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
で表される化合物等のモノ(メタ)アクリレート化合物:前記各種のモノ(メタ)アクリレート化合物の分子構造中に(ポリ)オキシエチレン鎖、(ポリ)オキシプロピレン鎖、(ポリ)オキシテトラメチレン鎖等の(ポリ)オキシアルキレン鎖を導入した(ポリ)オキシアルキレン変性体;前記各種のモノ(メタ)アクリレート化合物の分子構造中に(ポリ)ラクトン構造を導入したラクトン変性体等が挙げられる。
で表されるビカルバゾール化合物、下記構造式(5−1)又は(5−2)
で表されるフルオレン化合物等の芳香族ジ(メタ)アクリレート化合物;前記各種の芳香族ポリ(メタ)アクリレート化合物の分子構造中に(ポリ)オキシエチレン鎖、(ポリ)オキシプロピレン鎖、(ポリ)オキシテトラメチレン鎖等の(ポリ)オキシアルキレン鎖を導入した(ポリ)オキシアルキレン変性体;前記各種の芳香族ポリ(メタ)アクリレート化合物の分子構造中に(ポリ)ラクトン構造を導入したラクトン変性体等が挙げられる。
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
粒子径測定装置:大塚電子株式会社製「ELSZ−2」
粒子径測定サンプル:活性エネルギー線硬化型樹脂組成物を不揮発分1質量%のメチルイソブチルケトン溶液としたもの。
攪拌装置を備えた反応装置に、ε−カプロラクトン400質量部、ヒドロキシエチルアクリレート208質量部、ジブチル錫ジラウリート0.1質量部及びメトキノン0.1質量部を加え、攪拌しながら130℃で8時間反応させて、ラクトン変性ヒドロキシ(メタ)アクリレート化合物(x2−1)を得た。
撹拌装置を備えた反応装置に、ポリイソシアネート化合物(DIC株式会社製「バーノックDN−901S」ヘキサメチレンジイソシアネートのイソシアヌレート変性体、イソシアネート基含有量23.5質量%)342質量部、ジブチル錫ジラウリート2質量部及びメトキノン2質量部を加え、攪拌しながら60℃まで昇温した。次いで、前記ラクトン変性ヒドロキシ(メタ)アクリレート化合物(x2−1)658質量部を約一時間かけて分割投入した。80℃まで加熱して更に3時間反応させ、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了し、ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−1)を得た。ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−1)の重量平均分子量(Mw)は4,000、原料の仕込み比から算出される(メタ)アクリロイル基当量の理論値は523g/当量であった。
撹拌装置を備えた反応装置に、ジシクロヘキシルメタン−4,4’−ジイソシアネート252質量部、ジブチル錫ジラウリート2質量部及びメトキノン2質量部を加え、攪拌しながら60℃まで昇温した。次いで、前記ラクトン変性ヒドロキシ(メタ)アクリレート化合物(x2−1)757質量部を約一時間かけて分割投入した。80℃まで加熱して更に3時間反応させ、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了し、ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−2)を得た。ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−2)の重量平均分子量(Mw)は1,500、原料の仕込み比から算出される(メタ)アクリロイル基当量の理論値は460g/当量であった。
撹拌装置を備えた反応装置に、イソホロンジイソシアネート223質量部、ジブチル錫ジラウリート2質量部及びメトキノン2質量部を加え、攪拌しながら60℃まで昇温した。次いで、前記ラクトン変性ヒドロキシ(メタ)アクリレート化合物(x2−1)757質量部を約一時間かけて分割投入した。80℃まで加熱して更に3時間反応させ、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了し、ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−3)を得た。ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−3)の重量平均分子量(Mw)は1400、原料の仕込み比から算出される(メタ)アクリロイル基当量の理論値は450g/当量であった。
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置にメチルイソブチルケトン453質量部を仕込み、撹拌しながら系内温度が110℃になるまで加熱した。グリシジルメタアクリレート720質量部、メチルメタアクリレート480質量部およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)48質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間反応させた。90℃まで冷却し、メトキノン1.6質量部およびアクリル酸367質量部を仕込み、更にトリフェニルホスフィン7.8質量部を加えた。100℃まで加熱して8時間反応させ、(メタ)アクリロイル基含有アクリル樹脂(B3−1)のメチルイソブチルケトン溶液3000質量部(不揮発分50質量%)を得た。前記(メタ)アクリロイル基含有アクリル樹脂(B3−1)の重量平均分子量(Mw)は20,000、原料の仕込み比から算出される(メタ)アクリロイル基当量の理論値は309g/当量、水酸基価は182mgKOH/gであった。
・デンドリマー型(メタ)アクリレート樹脂(B2−1):MIWON社製「MIRAMER SP−1106」、重量平均分子量(Mw)1,630、一分子あたりの平均(メタ)アクリロイル基数18
・脂肪族炭化水素型ポリ(メタ)アクリレート化合物(B7−1):東亞合成株式会社製「DPA−600」、ジペンタエリスリトールペンタアクリレートとジペンタエリスリトールヘキサアクリレートとをモル比40/60で含有する組成物
・ラクトン変性脂肪族炭化水素型ポリ(メタ)アクリレート化合物(B7−2):日本化薬株式会社製「KAYARAD DPCA−60」、ジペンタエリスリトールが有する6つの水酸基全てが下記構造式(b)で表される構造部位で置換された化合物
下記要領で活性エネルギー線硬化型樹脂組成物及び積層フィルムを製造し、各種評価試験を行った。結果を表1に示す。
前記ラクトン変性ウレタン(メタ)アクリレート樹脂(B1−1)150質量部、前記(メタ)アクリロイル基含有アクリル樹脂(B3−1)のメチルイソブチルケトン溶液200質量部(樹脂固形分100質量部)、前記脂肪族炭化水素型ポリ(メタ)アクリレート化合物(B7-1)25質量部、無機微粒子(A−1)[日本アエロジル株式会社製「アエロジルR7200」、一次平均粒子径が12nmであり、粒子表面に(メタ)アクリロイル基を有するフュームドシリカ微粒子]225質量部、メチルイソブチルケトン400質量部を配合し、不揮発分50質量%のスラリーとしたものを、湿式ボールミル(アシザワ株式会社製「スターミルLMZ015」)を用いて混合分散し、分散体を得た。
メディア:メジアン径100μmのジルコニアビーズ
ミルの内容積に対する樹脂組成物の充填率:70体積%
攪拌翼の先端部の周速:12m/sec
樹脂組成物の流速:200ml/min
分散時間:60分
前記活性エネルギー線硬化型樹脂組成物をシクロオレフィンフィルム(膜厚100μm)上に硬化後の膜厚が2μmとなるようにバーコーターで塗布し、80℃で2分乾燥させた。窒素雰囲気下で高圧水銀灯を用いて500mJ/cm2の照射量で通過させて硬化させることにより、積層フィルムを得た。
スガ試験機株式会社製「ヘイズコンピュータ HZ−2」を用いて積層フィルムのヘイズ値を測定した。ヘイズ値が低いほど塗膜の透明性は高い。
下記条件で折り曲げ試験を行い、フィルムが破断するまでの回数で評価した。
屈曲速度1秒/サイクル、屈曲半径1mm、折り曲げ角度180°
スチールウール(日本スチールウール株式会社製「ボンスター#0000」)0.5gで直径2.4センチメートルの円盤状の圧子を包み、該圧子に500g重の荷重をかけて、積層フィルムの塗装表面を10往復させる磨耗試験を行った。磨耗試験前後の積層フィルムのヘーズ値をスガ試験機株式会社製「ヘーズコンピュータHZ−2」を用いて測定し、それらの差の値(ΔH)で評価した。
紫外線硬化型ハードコート剤(DIC株式会社製「ユニディック17−806」)をシクロオレフィンフィルム(膜厚100μm)上に硬化後の膜厚が2μmとなるようにバーコーターで塗布し、80℃で2分乾燥させた。窒素雰囲気下で高圧水銀灯を用いて500mJ/cm2の照射量で通過させて硬化させることにより、試験用フィルムを得た。
積層フィルムと試験用フィルムとを互いの塗装面同士が接するように重ね、荷重をかけて擦り合わせた。スムーズに滑る場合(アンチブロッキング性がある)をA、滑らない場合(ブロッキングする)をBとした。
先で作成した積層フィルムをスパッタ装置内に設置し、Arガス20cc/min雰囲気中、Cuターゲットを用いてスパッタリング法により、膜厚400nmの銅薄膜を有する導電性フィルムを得た。次いで、前記導電性フィルム上に形成された銅薄膜の表面に、JIS K−5400に準拠して、1mm角100個の碁盤目の粘着テープ剥離試験を実施した。剥離しない碁盤目数を計測して密着性を評価した。
分散体の配合を表1及び2に示す通りに変更した以外は実施例1と同様にして活性エネルギー線硬化型樹脂組成物を得、実施例1と同様にして各種試験を行った。結果を表1及び2に示す。
Claims (8)
- 無機微粒子(A)と(メタ)アクリロイル基を有するマトリックス樹脂(B)とを含有し、前記マトリックス樹脂(B)がラクトン変性ウレタン(メタ)アクリレート樹脂(B1)を必須の成分とする活性エネルギー線硬化型樹脂組成物。
- 前記無機微粒子(A)の平均粒子径が80〜250nmの範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記無機微粒子(A)と前記マトリックス樹脂(B)との質量比[(A)/(B)]が20/80〜60/40の範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記ラクトン変性ウレタン(メタ)アクリレート樹脂(B1)が、ポリイソシアネート化合物(x1)とラクトン変性ヒドロキシ(メタ)アクリレート化合物(x2)とを原料とする反応生成物である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記マトリックス樹脂(B)が、前記ラクトン変性ウレタン(メタ)アクリレート樹脂(B1)の他、デンドリマー型ポリ(メタ)アクリレート樹脂(B2)又は(メタ)アクリロイル基含有アクリル樹脂(B3)を含有する請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 請求項1〜5の何れか一つ記載の活性エネルギー線硬化型樹脂組成物を含有する塗料。
- 請求項6記載の塗料からなる塗膜。
- 請求項7記載の塗膜からなる層を有する積層フィルム。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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JP2016238463 | 2016-12-08 | ||
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JP2013244624A (ja) * | 2012-05-24 | 2013-12-09 | Toray Advanced Film Co Ltd | 筐体用表面被覆材 |
JP2014189745A (ja) * | 2013-03-28 | 2014-10-06 | Dic Corp | 活性エネルギー線硬化型樹脂組成物、その製造方法、塗料、塗膜、及びフィルム |
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