JP6705564B2 - 熱硬化型ウレタン樹脂組成物、フィルム及び物品 - Google Patents
熱硬化型ウレタン樹脂組成物、フィルム及び物品 Download PDFInfo
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- JP6705564B2 JP6705564B2 JP2019552752A JP2019552752A JP6705564B2 JP 6705564 B2 JP6705564 B2 JP 6705564B2 JP 2019552752 A JP2019552752 A JP 2019552752A JP 2019552752 A JP2019552752 A JP 2019552752A JP 6705564 B2 JP6705564 B2 JP 6705564B2
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- urethane resin
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- 239000011342 resin composition Substances 0.000 title claims description 47
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 47
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 46
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- 229920005862 polyol Polymers 0.000 claims description 83
- 239000004417 polycarbonate Substances 0.000 claims description 43
- 229920000515 polycarbonate Polymers 0.000 claims description 43
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 21
- 239000005056 polyisocyanate Substances 0.000 claims description 21
- 229920001228 polyisocyanate Polymers 0.000 claims description 21
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- 239000011248 coating agent Substances 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 17
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 13
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 13
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- 239000004359 castor oil Substances 0.000 description 1
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
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- 150000002222 fluorine compounds Chemical class 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- UFAPLAOEQMMKJA-UHFFFAOYSA-N hexane-1,2,5-triol Chemical compound CC(O)CCC(O)CO UFAPLAOEQMMKJA-UHFFFAOYSA-N 0.000 description 1
- GDZBYAPFZBVBEG-UHFFFAOYSA-N hexane-1,6-diol;hexane-2,5-diol Chemical compound CC(O)CCC(C)O.OCCCCCCO GDZBYAPFZBVBEG-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G18/6611—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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Description
本明細書において、ポリオール(a1)の数平均分子量は、ゲル・パーミエーション・クロマトグラフィ(GPC)により、ポリスチレンを標準試料として用いて得られる換算値を表す。
窒素導入管、温度計、攪拌機を備えた1リットル4つ口丸底フラスコに、メチルエチルケトン100重量部、酢酸エチル100重量部、あらかじめ50℃に加温して融解しておいた固体状ポリカーボネートジオール(エタナコール UH−200、宇部興産製)50重量部、トリメチロールプロパン5重量部を入れ攪拌した。ついで、ヘキサメチレンジイソシアネートを13質量部、ジブチル錫ジラウレート0.02重量部加えた。発熱に注意しながら内温を70℃に上昇させた後、温度を保ちながら攪拌し、さらに、液状ポリカーボネートジオール(デュラノールG3452、旭化成株式会社製)50質量部を加えて、撹拌を継続した。70℃に昇温後の撹拌継続時間は4時間であった。水酸基当量が2205であり、分子末端に水酸基を有するウレタンプレポリマーを含む主剤(i)を得た。
使用するポリオールとポリイソシアネート、架橋剤の種類及び量、得られるプレポリマーの水酸基の当量重量を表1〜2に示すように変更した以外は調製例1と同様にして分子末端に水酸基を有する主剤(ii)〜(xii)を得た。
表中、エタナコール UM−90は、液状ポリカーボネートジオール(エタナコール UM−90、宇部興産製)を表し、水添MDIは水添ジフェニルメタンジイソシアネートを表す。
得られた主剤を0℃に温調した部屋に3日間静置し、外観を目視で確認し、樹脂の白濁、沈降がなく溶液がクリアな状態であるものを優れると評価した。
調製例1で得られた主剤(i)100重量部と、ポリイソシアネート(ヘキサメチレンジイソシアネートヌレート体、バーノック 902S、DIC製)2.9重量部、レベリング剤(シルクリーン3700、ビックケミージャパン製)0.3重量部を混合してウレタン樹脂塗工液としての熱硬化型ウレタン樹脂組成物を得た。前記塗工液を離型処理の施されたポリエチレンテレフタラートフィルムへナイフコーターにより厚さ30μmで塗工し、更にオーブン中で110℃×2分間加熱し一次硬化させ、所定のフィルムを得た。
使用する主剤とポリイソシアネートの種類及び量、表1〜2に示すように変更した以外は実施例1と同様にして所定のフィルムを得た。
表中、デズモジュールWは、ジシクロヘキシルメタン−4,4’−ジイソシアネートを表す。
加熱硬化させて作製したフィルム表面を目視で観察し、ハジキや凹凸などがなく平坦であるものを○、ハジキや凹凸がありコーティング材として実用上使用できないものを×と評価した。
ベタツキがないものを○、ベタツキがないものを×と評価した ×:ベタツキがある。。
前記フィルムにマジック(PENTEL PEN、黒、中字)で線を書き込み、ティッシュペーパーで拭き取った際の拭き取りやすさを以下のように評価した
◎:5回の拭き取りでマジックが完全に除去される
〇:10回の拭き取りでマジックが完全に除去される
△:10回の拭き取りでマジックは一部除去されない。
×:10回の拭き取りでマジックはほとんど除去されない
前記フィルムに真鍮ブラシを500g荷重で塗膜に押し当て、10往復移動させた後、目視で傷の有無を確認し、以下のように評価した。
◎:1分以内で傷が回復
〇:10分以内で傷が回復
△:1時間以内で傷が回復
×:1時間を経過しても傷が回復しない
前記フィルムを幅1cm長さ5cmの短冊状に切り取り、株式会社島津製作所製「オートグラフAG−I」を用いてフィルムを引っ張り、伸び率(伸度)を測定した。
◎:200%以上
〇:100%以上200%未満
△:150%以上180%未満
×:100%未満
Claims (6)
- ポリオール(a1)、ポリイソシアネート(a2)及び鎖伸長剤(a3)を含む組成物から形成され末端に水酸基を有するウレタンプレポリマー(A)並びに有機溶剤(B)を含む主剤(i)と、硬化剤(ii)とを含む熱硬化型ウレタン樹脂組成物であって、
前記ポリオール(a1)が、芳香環を含まないポリオール(a1−1)を含むものであり、
前記芳香環を含まないポリオール(a1−1)が、25℃において液状のポリカーボネートポリオールと、25℃において固体状のポリカーボネートポリオールとを含むものであり、
前記ポリイソシアネート(a2)が、芳香環を含まないポリイソシアネート(a2−1)を含むものであり、
前記鎖伸長剤(a3)が、分子量500以下のトリオールを含むものであり、
前記硬化剤(ii)が、トリイソシアネートを含むものであり、
前記熱硬化型ウレタン樹脂組成物中、前記分子量500以下のトリオールと前記トリイソシアネートとの合計の含有率が、10質量%以上35質量%以下であることを特徴とする熱硬化型ウレタン樹脂組成物。 - 前記熱硬化型ウレタン樹脂組成物中、前記25℃において液状のポリカーボネートポリオールの含有率が、25質量%以上50質量%以下である請求項1記載の熱硬化型ウレタン樹脂組成物。
- 前記分子量500以下のトリオールが、トリメチロールプロパンである請求項1又は2記載の熱硬化型ウレタン樹脂組成物。
- 前記トリイソシアネートが、ヘキサメチレンジイソシアネートのイソシアヌレート体である請求項1〜3のいずれか1項記載の熱硬化型ウレタン樹脂組成物。
- 請求項1〜4のいずれか1項記載の熱硬化型ウレタン樹脂組成物の硬化塗膜を有することを特徴とするフィルム。
- 請求項5記載のフィルムを有することを特徴とする物品。
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