JP7375948B2 - 不飽和アクリル樹脂、活性エネルギー線硬化性樹脂組成物、硬化物及び物品 - Google Patents
不飽和アクリル樹脂、活性エネルギー線硬化性樹脂組成物、硬化物及び物品 Download PDFInfo
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- JP7375948B2 JP7375948B2 JP2022548467A JP2022548467A JP7375948B2 JP 7375948 B2 JP7375948 B2 JP 7375948B2 JP 2022548467 A JP2022548467 A JP 2022548467A JP 2022548467 A JP2022548467 A JP 2022548467A JP 7375948 B2 JP7375948 B2 JP 7375948B2
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- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 2
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920006174 synthetic rubber latex Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 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
- 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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
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)
撹拌棒、温度センサー、水冷コンデンサーが備え付けられたフラスコに酢酸ブチル65質量部を仕込み、乾燥窒素をフローし、撹拌しながら110℃に昇温した。メタクリル酸メチル47質量部、グリシジルメタクリル酸33質量部、ポリシロキサン化合物(A1)(JNC株式会社製「サイラプレーンFM-0701T」、数平均分子量423)2質量部、ポリシロキサン化合物(B1)(JNC株式会社製「サイラプレーンFM-7721」、数平均分子量5,000)1質量部、(2-エチルヘキサノイル)(tert-ブチル)ペルオキシド(日本油脂株式会社製「パーブチルO」)を5質量部、酢酸ブチル17質量部の混合溶液を滴下ロートから、4時間かけて滴下してアクリル重合を行った。粘度と不揮発分が一定になったことを確認してからフラスコを冷却し、80℃に到達したことを確認して、メチルハイドロキノン0.01質量部、トリフェニルホスフィン0.5質量部、アクリル酸17質量部を仕込んだ。105℃に昇温して、酸価3.0以下、エポキシ等量5,000以上であることを確認して、不飽和アクリル樹脂(1)を得た。このアクリル樹脂(1)の不揮発分は55質量%であり、数平均分子量(Mn)は4,600であり、重量平均分子量(Mw)は13,700であった。
撹拌棒、温度センサー、水冷コンデンサーが備え付けられたフラスコに、酢酸ブチル165質量部、イソホロンジイソシアネート(イソシアネート基含有量37.8質量%)111.0質量部、メチルハイドロキノン0.01質量部、ジブチルスズジラウレート0.1質量部を仕込み、60℃に昇温した。次いで、水酸基含有ポリシロキサン化合物(JNC株式会社製「サイラプレーンFM-DA11」、数平均分子量1,000、水酸基価94.7)296.2質量部を仕込んで、80℃で反応させた。残存イソシアネート基が3.1質量%となった時点で、更に、ペンタエリスリトール(トリ/テトラ)アクリレート(東亞合成株式会社製「アロニックスM-305」、水酸基価126mgKOH/g)120質量部を仕込み、そのまま反応を継続し、イソシアネート基が消失した時点で反応を終了して、ウレタン(メタ)アクリレート樹脂(R1)を得た。このウレタン(メタ)アクリレート樹脂(R1)の不揮発分は80質量%であった。
実施例1で得られたアクリル樹脂(1)に、光重合開始剤、紫外線吸収剤、光安定剤を固形分換算で表1に示す割合となるように配合し、酢酸ブチルで調整して不揮発分50質量%の活性エネルギー線硬化性樹脂組成物(1)を得た。
比較例1で得られたウレタン(メタ)アクリレート樹脂(R1)に、エチレン性不飽和化合物(東亞合成株式会社製「DPA-600T」、ジペンタエリスリトールヘキサアクリレート)、光重合開始剤、紫外線吸収剤、光安定剤を固形分換算で表1に示す割合となるように配合し、酢酸ブチルで調整して不揮発分50質量%の活性エネルギー線硬化性樹脂組成物(R1)を得た。
実施例及び比較例で得られた活性エネルギー線硬化性樹脂組成物を、ポリカーボネート基材上に、バーコーターを用いて、乾燥後の膜厚が10μmとなるように塗工し、70℃で5分間乾燥した後、高圧水銀灯ランプ(ランプ出力160W/cm)を用いて、積算照射量30kJ/m2となるように紫外線照射を行ない、硬化塗膜を形成した。得られた硬化塗膜の外観を目視にて観察し、以下の基準に従い評価した。
×:塗膜が白濁または塗膜表面にクレーターがあった。
前記硬化塗膜を用いて、塗膜表面に1mm間隔で10×10の碁盤目状にカッターナイフで切れ目を入れ、1mm2の碁盤目を100個作成した。次いで、碁盤目上にセロハンテープを貼りつけた後、急速に剥がし碁盤目試験を実施して、100個の碁盤目のうち残存した数を下記の基準に従い評価した。
△:残存数が、90個以上100個未満であった。
×:残存数が、90個未満であった。
撥水性の評価は、水接触角及び水滑落角の測定により行った。
前記ポリカーボネート基材上に形成した硬化塗膜について、協和界面科学社製「DMo-501」を用いて、精製水の接触角を測定した。数値が高い程、撥水性に優れている。
前記ポリカーボネート基材上に形成した硬化塗膜について、協和界面科学社製「DMo-501」を用いて、精製水の滑落角を測定した。滑落角は、水滴20μLを塗膜表面に乗せて、測定台を1°ずつ傾けた時に、水滴が2cm移動したときの角度を測定した。数値が低い程、滑落性に優れ、撥水性に優れている。なお、90°以上傾けても水滴が滑落しない場合、「×」と示した。
Claims (6)
- 1分子中に1つの(メタ)アクリロイル基を有するポリシロキサン化合物(A)、1分子中に少なくとも2つの(メタ)アクリロイル基を有するポリシロキサン化合物(B)、及びグリシジル(メタ)アクリレート(C)を含む重合性化合物の共重合体であるグリシジル基含有アクリル樹脂と、(メタ)アクリル酸(D)との反応物であり、重合性不飽和基を有し、酸価3.0以下、エポキシ当量5000以上であり、
前記ポリシロキサン化合物(A)が、下記一般式(1)で表され、
[式(1)中、R1は水素原子又はメチル基を表し、R2は炭素数2~10の炭化水素基を表し、R3はそれぞれ独立して炭素原子数1~4のアルキル基を表し、nは4~100の整数を表す。]
前記ポリシロキサン化合物(B)が、下記一般式(2)で表され、
[式(2)中、R1はそれぞれ独立して水素原子又はメチル基を表し、R2はそれぞれ独立して炭素数2~10の炭化水素基を表し、R3はそれぞれ独立して炭素数1~4のアルキル基を表し、nは4~100の整数を表す。]
前記ポリシロキサン化合物(A)の数平均分子量が、10,000未満であり、
前記ポリシロキサン化合物(B)の数平均分子量が、2,000以上15,000未満の範囲であることを特徴とする不飽和アクリル樹脂。 - 請求項1記載の不飽和アクリル樹脂と、
光重合開始剤とを含有することを特徴とする活性エネルギー線硬化性樹脂組成物。 - さらに、前記不飽和アクリル樹脂以外の重合性不飽和基を有する化合物を含有する請求項2記載の活性エネルギー線硬化性樹脂組成物。
- 前記重合性不飽和基を有する化合物が、1分子中に平均2~6個の重合性不飽和基を有するものである請求項3記載の活性エネルギー線硬化性樹脂組成物。
- 請求項2~4の何れか1項記載の活性エネルギー線硬化性樹脂組成物の硬化物。
- 請求項5の硬化物の塗膜を有する物品。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007314758A (ja) | 2006-04-25 | 2007-12-06 | Hitachi Chem Co Ltd | 硬化性樹脂組成物及び光学部材 |
JP2015187205A (ja) | 2014-03-26 | 2015-10-29 | 三菱化学株式会社 | 硬化性樹脂組成物、並びにこれを用いて得られる硬化物及び積層体 |
JP2016169295A (ja) | 2015-03-12 | 2016-09-23 | 三菱化学株式会社 | 硬化性組成物、硬化物及び積層体 |
WO2017065172A1 (ja) | 2015-10-13 | 2017-04-20 | 三菱レイヨン株式会社 | (メタ)アクリル系共重合体、樹脂組成物、防汚塗料組成物及び(メタ)アクリル系共重合体の製造方法 |
JP2018070742A (ja) | 2016-10-28 | 2018-05-10 | 東洋インキScホールディングス株式会社 | 活性エネルギー線硬化性樹脂組成物 |
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- 2022-02-10 JP JP2022548467A patent/JP7375948B2/ja active Active
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007314758A (ja) | 2006-04-25 | 2007-12-06 | Hitachi Chem Co Ltd | 硬化性樹脂組成物及び光学部材 |
JP2015187205A (ja) | 2014-03-26 | 2015-10-29 | 三菱化学株式会社 | 硬化性樹脂組成物、並びにこれを用いて得られる硬化物及び積層体 |
JP2016169295A (ja) | 2015-03-12 | 2016-09-23 | 三菱化学株式会社 | 硬化性組成物、硬化物及び積層体 |
WO2017065172A1 (ja) | 2015-10-13 | 2017-04-20 | 三菱レイヨン株式会社 | (メタ)アクリル系共重合体、樹脂組成物、防汚塗料組成物及び(メタ)アクリル系共重合体の製造方法 |
JP2018070742A (ja) | 2016-10-28 | 2018-05-10 | 東洋インキScホールディングス株式会社 | 活性エネルギー線硬化性樹脂組成物 |
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