JPWO2018123795A1 - 水性樹脂組成物、それを用いた積層体、光学フィルム及び画像表示装置 - Google Patents
水性樹脂組成物、それを用いた積層体、光学フィルム及び画像表示装置 Download PDFInfo
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- JPWO2018123795A1 JPWO2018123795A1 JP2018559112A JP2018559112A JPWO2018123795A1 JP WO2018123795 A1 JPWO2018123795 A1 JP WO2018123795A1 JP 2018559112 A JP2018559112 A JP 2018559112A JP 2018559112 A JP2018559112 A JP 2018559112A JP WO2018123795 A1 JPWO2018123795 A1 JP WO2018123795A1
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- OJGXBHHMMHJMLS-UHFFFAOYSA-J oxolane;zirconium(4+);tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].C1CCOC1 OJGXBHHMMHJMLS-UHFFFAOYSA-J 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical compound CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 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
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- 238000010998 test method Methods 0.000 description 1
- GXMNGLIMQIPFEB-UHFFFAOYSA-N tetraethoxygermane Chemical compound CCO[Ge](OCC)(OCC)OCC GXMNGLIMQIPFEB-UHFFFAOYSA-N 0.000 description 1
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- QLAGHGSFXJZWKY-UHFFFAOYSA-N triphenylborane;triphenylphosphane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QLAGHGSFXJZWKY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Abstract
Description
前記ウレタン樹脂(a2)が、芳香環を有するポリオール及び親水性基を有するポリオールを含有するポリオール(a2−1)と、ポリイソシアネート(a2−2)との反応物であることを特徴とする水性樹脂組成物、それを用いた積層体、光学フィルム及び画像表示装置に関するものである。
本明細書において、重量平均分子量、数平均分子量は、ゲル・パーミエーションクロマトグラフィ法により測定したポリスチレン換算値としてもとめることができる。
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、イソフタル酸27.6質量部、テレフタル酸27.6質量部、エチレングリコール11.7質量部、ジエチレングリコール19.9質量部及びジブチル錫オキサイド0.03質量部を仕込み180〜230℃で酸価が1以下になるまで230℃で24時間重縮合反応を行い、ポリエステルポリオール(1)〔酸価0.6、水酸基価50.0、芳香環濃度4.41mol/Kg〕を得た。
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、イソフタル酸35.4質量部、セバシン酸17.8質量部、アジピン酸7.8質量部、エチレングリコール6.2質量部、ネオペンチルグリコール22.9質量部、1,6−ヘキサンジオール11.7質量部及びジブチル錫オキサイド0.03質量部を仕込み180〜230℃で酸価が1以下になるまで230℃で24時間重縮合反応を行い、ポリエステルポリオール(2)〔酸価0.6、水酸基価42.5、芳香環濃度2.51mol/Kg〕を得た。
反応容器にクレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N−673−80M」、固形分エポキシ当量=209g/eq、不揮発分=80質量%、溶媒:メチルエチルケトン)を46.7質量部、アクリル酸13.3質量部、メトキノン0.08質量部、メチルエチルケトン13.3質量部を仕込み、攪拌させて均一に混合した。次いで、トリフェニルホスフィン0.37質量部を加え、反応温度80℃下で酸価が1.5以下になるまで反応させてビニルエステル樹脂(I)を得た。
反応容器に合成例1のポリエステルポリオール(1)75.7質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン67.89質量部を加え、攪拌し均一に混合した。次に、2,2−ジメチロールプロピオン酸6.1質量部を加え、次いで、イソホロンジイソシアネート20.3質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。イソシアネート値が0.1%以下になったのを確認し、n−ブタノール0.3質量部を加え、さらに2時間反応させた後、50℃まで冷却し、不揮発分が60質量%である芳香環を有するウレタン樹脂(II−1)を得た。
反応容器に合成例2のポリエステルポリオール(2)69質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン93.3質量部を加え、攪拌し均一に混合した。次に、1,4−ブタンジオール3.0質量部、2,2−ジメチロールプロピオン酸6.1質量部を加え、次いで、トリレンジイソシアネート19.4質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。イソシアネート値が0.1%以下になったのを確認し、n−ブタノール0.3質量部を加え、さらに2時間反応させた後、50℃まで冷却し、不揮発分51質量%である芳香環を有するウレタン樹脂(II−2)を得た。
反応容器にポリテトラメチレンエーテルグリコール(平均分子量2000)76.1質量部、メチルエチルケトン43.1質量部を加え、攪拌し均一に混合した。次に、2,2−ジメチロールプロピオン酸6.0質量部を加え、次いで、イソホロンジイソシアネート18.7質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。イソシアネート値が0.1%以下になったのを確認し、n−ブタノール0.3質量部を加え、さらに2時間反応させた後、50℃まで冷却し、不揮発分が70質量%であるウレタン樹脂(II−3)を得た。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、合成例3で得られたビニルエステル樹脂(I)136.1質量部、トリエチルアミン5.5質量部を加え、イオン交換水938.5質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が40質量%である複合樹脂組成物(A−1)を得た。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、フェノール系酸化防止剤(1)(分子量;640、融点;160℃)を1.28質量部、リン系酸化防止剤を1.28質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−1)水分散体を調製した。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、フェノール系酸化防止剤(1)を2.56質量部、リン系酸化防止剤を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水548質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23.5質量%である水性樹脂(B−2)水分散体を調製した。
合成例5で得られた芳香環を有するウレタン樹脂(II−2)に、フェノール系酸化防止剤を1.22質量部、リン系酸化防止剤を1.22質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.6質量部を加え、イオン交換水390質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が22.9質量%である水性樹脂(B−3)水分散体を調製した。
合成例6で得られたウレタン樹脂(II−3)に、フェノール系酸化防止剤を1.26質量部、リン系酸化防止剤を1.26質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水410質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23.3質量%である水性樹脂(B−4)水分散体を調製した。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、フェノール系酸化剤を1.28質量部、紫外線吸収剤を1.28質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−5)水分散体を調製した。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、フェノール系酸化剤を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−6)水分散体を調製した。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、リン系酸化剤を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−7)水分散体を調製した。
合成例4で得られた芳香環を有するウレタン樹脂(II−1)に、紫外線吸収剤を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−8)水分散体を調製した。
合成例4で得られたウレタン樹脂(II−1)に、フェノール系酸化防止剤(2)(分子量;1180、融点;120℃)を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−9)水分散体を調製した。
合成例4で得られたウレタン樹脂(II−1)に、フェノール系酸化防止剤(3)(分子量;350、融点;120℃)を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−10)水分散体を調製した。
合成例4で得られたウレタン樹脂(II−1)に、フェノール系酸化防止剤(4)(分子量;780、融点;240℃)を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水510質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−11)水分散体を調製した。
合成例4で得られたウレタン樹脂(II−1)に、フェノール系酸化防止剤(5)(分子量;530、融点;50℃)を2.56質量部加え、攪拌し均一に混合した。次に、トリエチルアミン4.8質量部を加え、イオン交換水410質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−12)水分散体を調製した。
合成例4で得られたウレタン樹脂(II−1)に、トリエチルアミン4.8質量部を加え、イオン交換水405質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30〜50℃にてメチルエチルケトンを除去し、不揮発分が23質量%である水性樹脂(B−13)水分散体を調製した。
製造例1で得られた複合樹脂組成物(A−1)100質量部と製造例2で得られた水性樹脂(B−1)水分散体2質量部とイオン交換水302.6質量部とを混合することによって不揮発分10質量%の水性樹脂組成物(1)を得た。
実施例1で用いた水性樹脂(B−1)水分散体に代えて、製造例3〜13で得た水性樹脂水分散体を用いた以外は、実施例1と同様に行い、水性樹脂組成物(2)〜(15)を得た。
UNIDIC V−5500(DIC株式会社製、エポキシアクリレート樹脂)70質量部、トリプロピレングリコールジアクリレート30質量部及びイルガキュア184(BASF社製、光重合開始剤)3質量部を混合することによって、光硬化性樹脂組成物(UV−1)を得た。
ポリエチレンテレフタレート(以下、「PET」と略記する。)製フィルム基材(厚さ125μm)の表面に、乾燥後の膜厚が約1μmとなるように、実施例1で得られた水性樹脂組成物(1)を塗布し、150℃で5分間加熱することによって、前記基材の表面にプライマー層(P−1)を形成した。
実施例15で用いた水性樹脂組成物(1)に代えて、実施例2〜15で得られた水性樹脂組成物(2)〜(15)を用いてプライマー層(P−2)〜(P−15)とした以外は、実施例13と同様に行い、積層体(2)〜(12)を得た。
膜厚125μmのポリエチレンテレフタレートからなる基材の表面に、乾燥時の膜厚が約1μmとなるようにプライマーを塗布し、150℃で5分間加熱することによって、前記基材の表面にプライマー層が積層した部材からなる試験板を作製した。次いで、前記試験板を用いて1mm碁盤目剥離試験を行った。具体的には、前記試験板のプライマー層の表面に1mm間隔で100個の碁盤目を作成し、その上にニチバン株式会社製の24mm幅の粘着テープを貼付した。
実施例及び比較例で得た積層体を用いて1mm碁盤目剥離試験を行った。実施例及び比較例で得た積層体を構成するUV塗膜の表面に、1mm間隔で100個の碁盤目を作成し、その上にニチバン株式会社製の24mm幅の粘着テープを貼付した。
前記得られた積層体に高圧水銀灯を光源として、照射強度0.5J/cm2で紫外線を所定の回数照射した後、前記積層体を取り出し、基材とプライマー層との密着性を、前記[基材とプライマー層との密着性(初期)]と同様の方法で評価した。なお、本発明でいうUV照射サイクル試験とは、あらかじめプライマー層にUV照射を所定の回数当てて意図的に塗膜を劣化させ、より過酷な条件下での密着性を評価する方法であり、これを用いて基材とプライマー層との密着性、及びプライマー層とUV塗膜との密着性の評価を実施するものである。
前記得られた積層体に高圧水銀灯を光源として、照射強度0.5J/cm2で紫外線を所定の回数照射した後、前記プライマー層の表面に、調製例1で得られた光硬化性樹脂組成物(UV−1)を15μmの塗膜厚で塗布し、高圧水銀灯を光源として、再度照射強度0.5J/cm2で紫外線を照射することによって、前記基材の表面にプライマー層を有し、そのプライマー層の表面にUV塗膜を有する積層体を得た。
次いで、前記積層体を取り出し、プライマー層とUV塗膜との密着性を、前記[プライマー層とUV塗膜との密着性(初期)]と同様の方法で評価した。
上記で得られた積層板のヘイズ値を、ヘイズメーター(スガ試験機株式会社製)を用いて測定した。JIS試験方法(JIS K7136:2000)に準拠した方法にて測定した。ヘイズ値(H)は下記計算式より算出した。また、PET基材のみのヘイズ値も測定し、そのヘイズ値は2.05%であった。
H(%)=Td/Tt×100
H;ヘイズ(曇値)(%)
Td;拡散透光率(%)
Tt;全光線透過率(%)
製造例1で得られた複合樹脂組成物(A−1)100質量部とイオン交換水300質量部とを混合することによって不揮発分10質量%の水性樹脂組成物(C1)を得た。
製造例2で得られた水性樹脂(B−1)水分散体100質量部とイオン交換水130質量部とを混合することによって不揮発分10質量%の水性樹脂組成物(C2)を得た。
製造例4で得られた水性樹脂(B−3)水分散体100質量部とイオン交換水130質量部とを混合することによって不揮発分10質量%の水性樹脂組成物(C3)を得た。
PET製フィルム基材(厚さ125μm)の表面に、乾燥後の膜厚が約1μmとなるように、比較例1で得られた水性樹脂組成物(C1)を塗布し、150℃で5分間加熱することによって、前記基材の表面にプライマー層(P’−1)を形成した。
比較例1で用いた水性樹脂組成物(C1)に代えて、比較例2〜3で得られた水性樹脂組成物(C2)〜(C3)を用いてプライマー層(P’−2)〜(P’−3)とした以外は、比較例1と同様に行い、積層体(R2)〜(R3)を得た。
実施例1で用いた水性樹脂(B−1)水分散体に代えて、製造例3〜13で得た水性樹脂水分散体を用いた以外は、実施例1と同様に行い、水性樹脂組成物(2)〜(15)を得た。ただし、実施例4は、参考例である。
Claims (12)
- ビニルエステル樹脂(a1)及び芳香環を有するウレタン樹脂(a2)を含有する複合樹脂(A)と、水性樹脂(B)と、水性媒体(C)とを含有する水性樹脂組成物であって、
前記ビニルエステル樹脂(a1)が、ノボラック型エポキシ樹脂及びビスフェノール型エポキシ樹脂からなる群より選ばれる1種以上のエポキシ樹脂(a1−1)と、酸基及び重合性不飽和基を有する化合物(a1−2)との反応物であり、
前記ウレタン樹脂(a2)が、芳香環を有するポリオール及び親水性基を有するポリオールを含有するポリオール(a2−1)と、ポリイソシアネート(a2−2)との反応物であることを特徴とする水性樹脂組成物。 - 前記水性樹脂(B)が、ウレタン樹脂(b1)である請求項1記載の水性樹脂組成物。
- さらに、非水溶性の添加剤を含有する請求項1又は2記載の水性樹脂組成物。
- 前記非水溶性の添加剤が、酸化防止剤、紫外線吸収剤からなる群より選ばれる1種以上の添加剤である請求項3記載の水性樹脂組成物。
- 前記酸化防止剤が、フェノール系酸化防止剤、リン系酸化防止剤からなる群より選ばれる1種以上の酸化防止剤である請求項4記載の水性樹脂組成物。
- 前記複合樹脂(A)と水性樹脂(B)との質量割合[(A)/(B)]が、99/1〜80/20の範囲である請求項1〜5のいずれか一項記載の水性樹脂組成物。
- 前記酸化防止剤の重量平均分子量が、500〜1,000の範囲である請求項1〜6のいずれか一項記載の水性樹脂組成物。
- 前記酸化防止剤の融点が、80〜180℃の範囲である請求項1〜7のいずれか一項記載の水性樹脂組成物。
- 基材の片面又は両面に、請求項1〜8のいずれか1項記載の水性樹脂組成物を用いて形成されたプライマー層を有し、前記プライマー層の表面に、活性エネルギー線硬化性組成物の硬化塗膜を有することを特徴とする積層体。
- 前記活性エネルギー線硬化性樹脂組成物が、重合性不飽和基を有する樹脂と、重合性不飽和基を有する単量体とを含有するものである請求項9記載の積層体。
- 請求項9又は10記載の積層体を有することを特徴とする光学フィルム。
- 請求項11記載の光学フィルムを有することを特徴とする画像表示装置。
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