JP6676946B2 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP6676946B2 JP6676946B2 JP2015241464A JP2015241464A JP6676946B2 JP 6676946 B2 JP6676946 B2 JP 6676946B2 JP 2015241464 A JP2015241464 A JP 2015241464A JP 2015241464 A JP2015241464 A JP 2015241464A JP 6676946 B2 JP6676946 B2 JP 6676946B2
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- 125000004122 cyclic group Chemical group 0.000 claims description 30
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
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- 235000002597 Solanum melongena Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 238000004381 surface treatment Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VUYXVWGKCKTUMF-UHFFFAOYSA-N tetratriacontaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO VUYXVWGKCKTUMF-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Landscapes
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Description
で表されるラジカル重合性化合物、及び単官能ラジカル重合性モノマーを含む反応性モノマーと、直鎖状又は分岐状の重合体(第二の重合体)と、チキソ剤と、を含有する。式(I)中、X、R1及びR2がそれぞれ独立に2価の有機基で、R3及びR4がそれぞれ独立に水素原子又はメチル基である。樹脂組成物中で反応性モノマーが重合することで、それら反応性モノマーに由来するモノマー単位から構成される第一の重合体が生成する。これにより、反応生成物が硬化して、塗膜(硬化体)を形成する。第一の重合体は、通常、第二の重合体と共有結合によって結合することなく、第二の重合体とは別の重合体として塗膜中に形成される。
で表される基であってもよい。式(10)中、Yは置換基を有していてもよい環状基で、Z1及びZ2はそれぞれ独立に炭素原子、酸素原子、窒素原子、及び硫黄原子から選ばれる原子を含む官能基で、i及びjはそれぞれ独立に0〜2の整数である。*は結合手を表す(これは他の式でも同様である)。Xが式(10)の基であると、式(II)の環状のモノマー単位が特に形成され易いと考えられる。環状基Yに対するZ1及びZ2の配置が、シス位であってもよいし、トランス位であってもよい。Z1及びZ2は、−O−、−OC(=O)−、−S−、−SC(=O)−、−OC(=S)−、−NR10−(R10は水素原子又はアルキル基)、又は−ONH−で表される基であってもよい。
合成例1:trans−1,2−ビス(2−アクリロイルオキシエチルカルバモイルオキシ)シクロヘキサン(BACH)の合成
100mL二口ナスフラスコにtrans−1,2−シクロヘキサンジオール(2.32g、20.0mmol)を加え、フラスコ内を窒素置換した。そこに乾燥したジクロロメタン(40mL)、及びジラウリン酸ジブチル錫(11.8μL、0.10mol%:0.020mmol)を入れた。フラスコ中の反応液に2−アクリロイルオキシエチルイソシアネート(5.93g、42.0mmol)のジクロロメタン(4mL)溶液を滴下ロートから滴下し、反応液を30℃で24時間撹拌して、反応を進行させた。反応終了後、反応液にジエチルエーテルを加えて飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた後、溶媒を減圧留去した。残渣をアセトニトリルに溶解させ、得られた溶液をヘキサンで3回洗浄した。溶媒を減圧留去し、残渣をジエチルエーテル及びヘキサンの混合溶媒からの再結晶によって精製して、BACHの白色結晶を得た。収量は、5.1gであり、収率は、64質量%であった。
20mLナスフラスコにポリエチレングリコール(PEG1500、750mg、0.500mmol、数平均分子量1500)、ポリプロピレングリコール(PPG4000、2000mg、0.500mmol、数平均分子量4000)を加えてからフラスコ内を窒素置換し、内容物を115℃で融解させた。融解液に4,4’−ジシクロヘキシルメタンジイソシアネート(262mg、1.00mmol)を加えて、窒素雰囲気下、115℃で24時間撹拌して、PEG−PPGオリゴマー(ポリオキシエチレン鎖及びポリオキシプロプレン鎖を含む第二の重合体)を得た。
合成例1のBACH、合成例2のPEG−PPGオリゴマー、アクリロニトリル、2−エチルヘキシルアクリレート及び2,2’−アゾビス−イソブチロニトリルを表1に示す質量比で混合した。得られた混合液に、チキソ剤としてAEROSIL200、及びメチルイソブチルケトンを表1に示す質量比で混合した分散液を加えて撹拌し、実施例及び比較例の混合液(樹脂組成物)を得た。
得られた混合液を、乾燥後の膜厚が25〜35μmになるように鋼板にスプレー塗装した後、100℃で1時間加熱することで、塗膜を有する試験板を得た。
得られた試験板について、JIS K−5400の碁盤目試験法に従って、密着性を評価した。すなわち、試験板の塗膜にナイフにて2mm間隔で縦横各10本線状に切り傷をつけることで100個の碁盤目を作製し、その上にセロハンテープを貼り付けた。1〜2分後に、塗膜に対して直角となるようにセロハンテープを剥離した。試験板の塗膜を目視で観察し、100個全ての碁盤目において塗膜が残った場合を「良」、80個以上100個未満の碁盤目において塗膜が残った場合を「可」、80個未満の碁盤目において塗膜が残った場合を「不良」と判定した。
得られた試験板を50℃の温水に168時間浸漬し、上記密着性の評価と同様の方法で温水への浸漬時における密着性、すなわち、耐水性を評価した。
テーバー式アブレーションテスター(安田精機製作所製)を用いて、得られた試験板の塗膜を0.2g/cm2の加重で磨耗し、塗膜の傷を目視で観察した。傷が認められなかったものを「良」、傷が認められたものを「不良」と判定した。
Claims (5)
- 式(I):
で表され、X、R1及びR2がそれぞれ独立に2価の有機基で、R3及びR4がそれぞれ独立に水素原子又はメチル基である、ラジカル重合性化合物、及び単官能ラジカル重合性モノマーを含む反応性モノマーと、
直鎖状又は分岐状の重合体と、
チキソ剤と、
を含有し、
前記式(I)中のXが、下記式(10):
で表され、Yが下記式(11)、(12)、(13)、(14)又は(15):
で表される環状基で、*が結合手を表し、Z 1 及びZ 2 がそれぞれ独立に−O−、−OC(=O)−、−S−、−SC(=O)−、−OC(=S)−、−NR 10 −(R 10 は水素原子又はアルキル基)、又は−ONH−で表される基で、i及びjがそれぞれ独立に0〜2の整数で、*が結合手を表す、基であり、
前記式(I)中のR 1 及びR 2 が、下記式(20):
で表され、R 6 が炭素数1〜8の炭化水素基で、前記式(I)中の窒素原子に結合し、Z 3 が−O−、又は−NR 10 −(R 10 は水素原子又はアルキル基)で表される基で、*が結合手を表す、基であり、
前記重合体が、ポリオキシアルキレン鎖を含む重合体である樹脂組成物。 - 前記重合体が、2以上の線状鎖と、前記線状鎖の末端同士を連結する連結基と、を含む重合体であり、前記連結基が、環状基を含む有機基又は分岐状の有機基である、請求項1に記載の樹脂組成物。
- 前記単官能ラジカル重合性モノマーが、置換基を有していてもよい炭素数1〜16のアルキル基を有するアルキル(メタ)アクリレートを含む、請求項1又は2に記載の樹脂組成物。
- 前記単官能ラジカル重合性モノマーが、アクリロニトリルを含む、請求項1〜3のいずれか一項に記載の樹脂組成物。
- 前記重合体の重量平均分子量が5000以上である、請求項1〜4のいずれか一項に記載の樹脂組成物。
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