JP5517262B2 - 樹脂組成物及び塗膜 - Google Patents
樹脂組成物及び塗膜 Download PDFInfo
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- JP5517262B2 JP5517262B2 JP2011138303A JP2011138303A JP5517262B2 JP 5517262 B2 JP5517262 B2 JP 5517262B2 JP 2011138303 A JP2011138303 A JP 2011138303A JP 2011138303 A JP2011138303 A JP 2011138303A JP 5517262 B2 JP5517262 B2 JP 5517262B2
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- resin composition
- polyamide
- coating film
- acrylic copolymer
- amide group
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims description 55
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- 125000003368 amide group Chemical group 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 36
- 229920002647 polyamide Polymers 0.000 claims description 34
- 229920006243 acrylic copolymer Polymers 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- -1 polyol compound Chemical class 0.000 claims description 19
- 239000002994 raw material Substances 0.000 claims description 19
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- 229920005862 polyol Polymers 0.000 claims description 13
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- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 4
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004953 Aliphatic polyamide Substances 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- IAXXETNIOYFMLW-GYSYKLTISA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C(=C)C)C[C@@H]1C2(C)C IAXXETNIOYFMLW-GYSYKLTISA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 2
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- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004763 nomex Substances 0.000 description 1
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Landscapes
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Description
攪拌機、冷却機、窒素封入機、温度計及びモノマー滴下装置を備えた1リットルの4つ口フラスコにメチルイソブチルケトンを200g仕込み、内部温度が90℃になるまで加温した。そこへ、表1に示す実施例1〜実施例9、比較例1又は比較例2の混合溶液を1時間にわたって滴下し、90℃で4時間保持し、反応を終了して、樹脂組成物を得た。表1に、実施例1〜実施例9、比較例1及び比較例2の混合溶液の組成と得られた共重合体のガラス転移点、水酸基価及び質量平均分子量とを示す。
得られた樹脂組成物60部と、繊維素系樹脂としてセルロースアセテートブチレート(CAB)の10%溶液(EASTMAN社製、CAB381−2)30部と、アルミニウム顔料(東洋アルミニウム社製、FZ−5660、44%品)12部と、酢酸エチル12部とを混合した混合溶液を酢酸イソブチルで希釈して粘度調整した後、ポリイソシアネート化合物(住化バイエルウレタン社製、スミジュールN-3200)を樹脂組成物中の水酸基のモル当量(アクリル系共重合体が有する水酸基のモル当量)とポリイソシアネート化合物のイソシアネート基のモル当量との比(NCO/OH)が、1.2となるように配合して塗料を得た。
得られた塗料をポリアミド系基材(東レ社製、アミラン(登録商標))上にスプレーコート法で、塗装後の厚さが20±5μmとなるように塗装し、90℃で60分強制乾燥を行い、塗膜を形成した。
塗膜の表面を目視で観察し、次のとおり評価した。
○:塗装ムラがなく、輝度感がある(実用レベル)。
×:塗装ムラがあり、輝度感がない(実用不適)。
JIS K5600−5−6:1999「クロスカット法」に準じて、1mm×1mmの碁盤目状の切込みを100個入れ、粘着テープによる剥離試験を行った。評価基準についても同規格に準じて評価を行った。
○:剥離なし(実用レベル)。
×:1升以上の剥離(実用不適)。
雰囲気温度50℃及び雰囲気湿度95%RHの恒温恒湿槽中に500時間静置後、粘着テープによる剥離試験を行った。試験方法並びに判定基準は初期付着性と同様である。
雰囲気温度80℃の恒温槽中に300時間静置後、粘着テープによる剥離試験を行った。試験方法並びに判定基準は初期付着性と同様である。
40℃の温水に500時間浸漬後、粘着テープによる剥離試験を行った。試験方法並びに判定基準は初期付着性と同様である。
動物性脂を1g/m2塗布し、雰囲気温度50℃の恒温槽中に72時間静置後、粘着テープによる剥離試験を行った。試験方法並びに判定基準は初期付着性と同様である。
平面摩耗試験機(東洋精機製作所社製 摺動式摩耗試験機)を用いて、エタノールを染み込ませたガーゼを、塗膜上を2.0Nで10往復ラビング後、塗膜の表面状態を目視で確認した。評価基準は次のとおりである。
○:塗膜表面状態に大きな変化なし(実用レベル)。
×:塗膜の一部又は全部が剥離して、基材が露出した(実用不適)。
Claims (6)
- ポリオール化合物を含有し、かつ、ポリイソシアネート化合物と混合すると反応して硬化し、基材上に塗膜を形成する樹脂組成物において、
前記ポリオール化合物が、共重合させる原料として、
(a)ヒドロキシエチルアクリルアミド、又は、ヒドロキシエチルアクリルアミド及びアミド基含有ビニル系モノマー、
(b)水酸基及びアミド基を含有しないエチレン性不飽和モノマー、
(c)メタクリル酸、
の(a),(b)及び(c)の組合せだけを用いてなるアクリル系共重合体であり、
前記アクリル系共重合体中の水酸基とアミド基とのモル比率(アミド基/水酸基)が、1.0〜2.0であることを特徴とする樹脂組成物。 - ポリオール化合物を含有し、かつ、ポリイソシアネート化合物と混合すると反応して硬化し、基材上に塗膜を形成する樹脂組成物において、
前記ポリオール化合物が、共重合させる原料として、
(a)ヒドロキシエチルアクリルアミド、又は、ヒドロキシエチルアクリルアミド及びアミド基含有ビニル系モノマー、
(b)水酸基及びアミド基を含有しないエチレン性不飽和モノマー、
(c)メタクリル酸、
の(a),(b)及び(c)の組合せだけを用いてなるアクリル系共重合体であり、
前記アクリル系共重合体が、共重合させる原料中の水酸基の合計モル数とアミド基の合計モル数とのモル比率(アミド基/水酸基)を1.0〜2.0で配合して、共重合したものであることを特徴とする樹脂組成物。 - 前記アクリル系共重合体のガラス転移点が、−20〜60℃であることを特徴とする請求項1又は2に記載の樹脂組成物。
- 前記アクリル系共重合体の水酸基価が、10〜50mg/KOHであることを特徴とする請求項1〜3のいずれか一つに記載の樹脂組成物。
- 前記基材は、ポリアミド系基材であることを特徴とする請求項1〜4のいずれか一つに記載の樹脂組成物。
- 請求項1〜5のいずれか一つに記載の樹脂組成物とポリイソシアネート化合物とを含有し、かつ、ポリアミド系基材上に設けられていることを特徴とする塗膜。
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