JP6392914B2 - ハードコーティングフィルム - Google Patents
ハードコーティングフィルム Download PDFInfo
- Publication number
- JP6392914B2 JP6392914B2 JP2017017844A JP2017017844A JP6392914B2 JP 6392914 B2 JP6392914 B2 JP 6392914B2 JP 2017017844 A JP2017017844 A JP 2017017844A JP 2017017844 A JP2017017844 A JP 2017017844A JP 6392914 B2 JP6392914 B2 JP 6392914B2
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- Prior art keywords
- hard coating
- compound
- coating film
- group
- meth
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims description 84
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- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 36
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
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- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 7
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- 125000002947 alkylene group Chemical group 0.000 claims description 3
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- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 2
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 229940097362 cyclodextrins Drugs 0.000 claims 1
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
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- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
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- XOAKHODFHUHKSO-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C(C)C1=CC=2C(C3=CC=CC=C3SC2C(=C1)CC)=O.C(C)C1=CC=2C(C3=CC=CC=C3SC2C(=C1)CC)=O XOAKHODFHUHKSO-UHFFFAOYSA-N 0.000 description 1
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
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- 238000007607 die coating method Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YDZANNORUSYHFB-UHFFFAOYSA-N phenacyl benzoate Chemical compound C=1C=CC=CC=1C(=O)COC(=O)C1=CC=CC=C1 YDZANNORUSYHFB-UHFFFAOYSA-N 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
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C08G18/81—Unsaturated isocyanates or isothiocyanates
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Description
合成例1
カプロラクトンがグラフティングされているポリロタキサンポリマー[A1000、Advanced Soft Material INC]50gを反応器に投入した後、Karenz−AOI[2−acryloylethyl isocyanate、Showadenko(株)]4.53g、ジブチル錫ジラウレート[DBTDL、Merck社]20mg、ヒドラキノンモノメチレンエテール(Hydroquinone monomethylene ether)110mgおよびメチルエチルケトン315gを添加して70℃で5時間反応させて、末端にアクリレート系化合物が導入されたポリラクトン系化合物が結合されたシクロデキストリンを環状化合物として含むポリロタキサンポリマー液(固形分15%)を得た。
カプロラクトンがグラフティングされているポリロタキサンポリマー[A1000、Advanced Soft Material INC]50gを反応器に投入した後、Karenz−AOI[2−acryloylethyl isocyanate、Showadenko(株)]9.06g、ジブチル錫ジラウレート[DBTDL、Merck社]20mg、ヒドラキノンモノメチレンエテール110mgおよびメチルエチルケトン315gを添加して70℃で5時間反応させて、末端にアクリレート系化合物が導入されたポリラクトン系化合物が結合されたシクロデキストリンを環状化合物として含むポリロタキサンポリマー液(固形分15%)を得た。
100mlのフラスコにカプロラクトンがグラフティングされているポリロタキサンポリマー[A1000、Advanced Soft Material INC]5gを投入した後、2−Isocyanatoethyl acrylate(AOI−VM、Showadenko(株))1.358g、ジブチル錫ジラウレート[DBTDL、Merck社]2mg、ヒドラキノンモノメチレンエテール11mgおよびメチルエチルケトン31.5gを添加して70℃で5時間反応させて、末端にアクリレート系化合物が導入されたポリラクトン系化合物が結合されたシクロデキストリンを環状化合物として含むポリロタキサンポリマー液(固形分14.79%)を得た。
実施例1
(1)光硬化性コーティング組成物の製造
前記合成例1で得られたポリロタキサン100重量部に対して、ジペンタエリトリトールヘキサアクリレート100重量部、ペンタエリトリトールヘキサアクリレート50重量部、UA−200PA(多官能ウレタンアクリレート、新中村社)50重量部および光重合開始剤であるIrgacure−184 10重量部をメチルエチルケトン、酢酸エチルおよび酢酸ブチルを含む混合溶媒に固形分50%になるように混合して光硬化性コーティング組成物(E1)を製造した。
前記で得られた光硬化性コーティング組成物をそれぞれTACフィルム(厚さ40μm)にワイヤーバー(8号)を用いてコーティングした。そして、コーティング物を90℃で2分間乾燥した後、200mJ/cm2の紫外線を5秒間照射して硬化した。そして、前記硬化物を130℃オーブンで5分間加熱処理して5μmの厚さを有するハードコーティングフィルムを製造した。
(1)光硬化性コーティング組成物の製造
前記合成例2で得られたポリロタキサンを用いた点を除いては、実施例1と同様な方法で光硬化性コーティング組成物(E2)を製造した
(2)ハードコーティングフィルムの製造
前記光硬化性コーティング組成物(E2)を用いた点を除いては、実施例1と同様な方法でハードコーティングフィルムを製造した。
(1)光硬化性コーティング組成物の製造
前記合成例3で得られたポリロタキサンを用いた点を除いては、実施例1と同様な方法で光硬化性コーティング組成物(CE)を製造した
(2)ハードコーティングフィルムの製造
前記光硬化性コーティング組成物(CE)を用いた点を除いては、実施例1と同様な方法でハードコーティングフィルムを製造した。
前記実施例で得られたコーティングフィルムの物性を下記のように評価した。
Claims (16)
- ラクトン系化合物が結合された環状化合物、前記環状化合物を貫通する線状分子、および前記線状分子の両末端に配置されて前記環状化合物の離脱を防止する封鎖基、を含むポリロタキサン化合物(a)とバインダー樹脂(b)との間の架橋物を含むハードコーティング層を含み、
前記ラクトン系化合物の末端中30モル%〜60モル%が非置換され、
前記ラクトン系化合物の末端に(メタ)アクリレート系作用基が40モル%〜70モル%導入される、
ハードコーティングフィルム。 - 前記ラクトン系化合物の末端中45モル%〜65モル%に(メタ)アクリレート系作用基が置換され、前記ラクトン系化合物の末端中35モル%〜55モル%にヒドロキシ作用基が残留する、請求項1に記載のハードコーティングフィルム。
- 前記環状化合物は、α−シクロデキストリンおよびβ−シクロデキストリンおよびγ−シクロデキストリンからなる群より選ばれた1種以上を含む、請求項1または2に記載のハードコーティングフィルム。
- 前記ラクトン系化合物は、直接結合または炭素数1〜10の直鎖または分枝鎖のオキシアルキレン基を介して前記環状化合物に結合された、請求項1〜3のいずれか一項に記載のハードコーティングフィルム。
- 前記ラクトン系化合物の残基は、下記化学式1の作用基を含む、請求項1〜4のいずれか一項に記載のハードコーティングフィルム。
- 前記(メタ)アクリレート系作用基が、直接結合、ウレタン結合、エーテル結合、チオエステル結合またはエステル結合を通じて前記ラクトン系化合物の残基に結合された、請求項1〜5のいずれか一項に記載のハードコーティングフィルム。
- 前記(メタ)アクリレート系作用基は、下記化学式2の作用基を含む、請求項1〜6のいずれか一項に記載のハードコーティングフィルム。
- 前記線状分子は、ポリオキシアルキレン系化合物またはポリラクトン系化合物である、請求項1〜7のいずれか一項に記載のハードコーティングフィルム。
- 前記線状分子は、1,000〜50,000の重量平均分子量を有する、請求項1〜8のいずれか一項に記載のハードコーティングフィルム。
- 前記封鎖基は、ジニトロフェニル基、シクロデキストリン基、アダマンタン基、トリチル基、フルオレセイン基およびピレン基からなる群より選ばれた1種以上の作用基を含む、請求項1〜9のいずれか一項に記載のハードコーティングフィルム。
- 前記ポリロタキサン化合物は、100,000〜800,000の重量平均分子量を有する、請求項1〜10のいずれか一項に記載のハードコーティングフィルム。
- 前記バインダー樹脂は、ポリシロキサン系樹脂、(メタ)アクリレート系樹脂およびウレタン(メタ)アクリレート系樹脂からなる群より選ばれた1種以上の高分子樹脂またはこれらの共重合体を含む、請求項1〜11のいずれか一項に記載のハードコーティングフィルム。
- 前記ハードコーティング層は、1kg荷重下で5H以上の鉛筆硬度を有する、請求項1〜12のいずれか一項に記載のハードコーティングフィルム。
- 前記ポリロタキサン化合物(a)とバインダー樹脂(b)との間の架橋物に分散している無機微細粒子をさらに含む、請求項1〜13のいずれか一項に記載のハードコーティングフィルム。
- 前記ハードコーティング層は、1〜300μmの厚さを有する、請求項1〜14のいずれか一項に記載のハードコーティングフィルム。
- 前記ハードコーティング層と結合された高分子樹脂基材層をさらに含む、請求項1〜15のいずれか一項に記載のハードコーティングフィルム。
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JP5859170B2 (ja) | 2012-05-25 | 2016-02-10 | エルジー・ケム・リミテッド | ポリロタキサン化合物、光硬化性コーティング組成物およびコーティングフィルム |
KR101379491B1 (ko) | 2012-05-31 | 2014-04-01 | 주식회사 엘지화학 | 하드코팅 필름 및 이의 제조방법 |
KR101418409B1 (ko) | 2012-05-31 | 2014-07-09 | 주식회사 엘지화학 | 하드코팅 조성물 |
KR101501686B1 (ko) | 2012-05-31 | 2015-03-11 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101470465B1 (ko) | 2012-08-23 | 2014-12-08 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101436616B1 (ko) | 2012-08-23 | 2014-09-03 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101470464B1 (ko) | 2012-08-23 | 2014-12-08 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101470463B1 (ko) | 2012-08-23 | 2014-12-08 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101415839B1 (ko) | 2012-08-23 | 2014-07-09 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101415840B1 (ko) | 2012-08-23 | 2014-07-09 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101470466B1 (ko) | 2012-08-23 | 2014-12-08 | 주식회사 엘지화학 | 적층 하드코팅 필름 |
US9657127B2 (en) | 2013-01-21 | 2017-05-23 | Sumitomo Seika Chemicals Co., Ltd. | Composition for soft materials, and soft material |
KR101587190B1 (ko) | 2013-03-15 | 2016-01-20 | 주식회사 엘지화학 | 플라스틱 필름 |
KR101745678B1 (ko) * | 2013-05-09 | 2017-06-09 | 주식회사 엘지화학 | 고분자 필름, 플렉서블 발광 소자 디스플레이 장치 및 감김 가능 디스플레이 장치 |
KR20140147041A (ko) * | 2013-06-18 | 2014-12-29 | 주식회사 엘지화학 | 셀 포장재료 및 그 제조방법 |
ES2688493T3 (es) * | 2013-10-31 | 2018-11-02 | Sumitomo Seika Chemicals Co., Ltd. | Composición que contiene polirotaxano |
WO2015076567A1 (ko) * | 2013-11-19 | 2015-05-28 | 주식회사 엘지화학 | 플라스틱 필름 적층체 |
KR101671431B1 (ko) | 2013-11-19 | 2016-11-01 | 주식회사 엘지화학 | 플라스틱 필름 |
KR101686644B1 (ko) | 2013-11-19 | 2016-12-14 | 주식회사 엘지화학 | 플라스틱 필름 적층체 |
JP6526972B2 (ja) * | 2014-01-14 | 2019-06-05 | 日東電工株式会社 | 接着剤、偏光フィルム、液晶パネル、光学フィルム、および画像表示装置 |
CN104086675B (zh) * | 2014-06-30 | 2016-05-04 | 京东方科技集团股份有限公司 | 环糊精衍生物及其制备方法、光阻组合物和显示装置 |
KR102387237B1 (ko) | 2014-11-04 | 2022-04-18 | 가부시키가이샤 에이에스엠 | 광경화성 조성물, 광경화성 조성물로 형성되는 경화체, 및 해당 경화체의 제조 방법 |
KR101971011B1 (ko) * | 2015-06-02 | 2019-04-22 | 후지필름 가부시키가이샤 | 하드 코트 필름, 화상 표시 소자의 전면판, 저항막식 터치 패널, 정전 용량식 터치 패널 및 화상 표시 장치 |
KR102407539B1 (ko) * | 2015-08-26 | 2022-06-13 | 엘지디스플레이 주식회사 | 하드코팅층, 이의 제조 방법 및 이를 포함하는 표시장치 |
JP2017068100A (ja) * | 2015-09-30 | 2017-04-06 | 株式会社フジシールインターナショナル | シュリンクラベル |
KR102590498B1 (ko) * | 2016-02-19 | 2023-10-19 | 삼성디스플레이 주식회사 | 플렉서블 표시장치, 윈도우 부재의 제조방법 및 하드 코팅 조성물 |
CN108474870A (zh) | 2016-03-09 | 2018-08-31 | 株式会社Lg化学 | 抗反射膜 |
SG10202101422PA (en) | 2016-08-10 | 2021-03-30 | Tokuyama Corp | Photochromic curable composition, use thereof, and polyrotaxane monomers |
JPWO2018038124A1 (ja) * | 2016-08-23 | 2019-06-24 | 国立大学法人大阪大学 | 重合性官能基で修飾されたポリロタキサン及びその製造方法、並びに高分子材料及びその製造方法 |
KR102651384B1 (ko) | 2016-11-28 | 2024-03-25 | 엘지디스플레이 주식회사 | 규소 화합물, 이를 포함하는 하드코팅 필름 및 표시장치 |
US10804537B2 (en) * | 2017-08-14 | 2020-10-13 | Global Graphene Group, Inc. | Protected particles of anode active materials, lithium secondary batteries containing same and method of manufacturing |
JP7100310B2 (ja) * | 2017-11-29 | 2022-07-13 | 横浜ゴム株式会社 | 微粒子 |
TW201932537A (zh) * | 2017-12-26 | 2019-08-16 | 日商尼歐斯股份有限公司 | 硬化性樹脂組成物及自我修復性材料 |
DE102018107702A1 (de) | 2018-03-29 | 2019-10-02 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gmbh | Nanostrukturierte Kompositmaterialien mit selbstheilenden Eigenschaften |
JP7155471B2 (ja) * | 2018-04-09 | 2022-10-19 | サムソン エレクトロ-メカニックス カンパニーリミテッド. | ポジ型感光性組成物、及び、感光性組成物の製造方法 |
JP7061531B2 (ja) * | 2018-07-26 | 2022-04-28 | 株式会社ネオス | 硬化性樹脂組成物及び自己修復性材料 |
JP7354536B2 (ja) * | 2018-12-19 | 2023-10-03 | 富士フイルムビジネスイノベーション株式会社 | 積層部材 |
CN114133540B (zh) * | 2021-06-11 | 2022-10-14 | 电子科技大学 | 一种自修复材料、自愈合涂层、自愈合显示元件及制备工艺 |
CN115232509A (zh) * | 2022-08-15 | 2022-10-25 | 亚士漆(上海)有限公司 | 弹性体混合物及其应用以及包含其的自修复乳胶漆涂料 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100714742B1 (ko) | 2000-07-03 | 2007-05-07 | 가부시키가이샤 재팬 티슈 엔지니어링 | 조직 재생용 기재, 이식용 재료 및 그의 제법 |
JP4821005B2 (ja) * | 2004-01-08 | 2011-11-24 | 国立大学法人 東京大学 | 架橋ポリロタキサンを有する化合物及びその製造方法 |
JP4521875B2 (ja) * | 2005-08-31 | 2010-08-11 | 日産自動車株式会社 | 疎水性修飾ポリロタキサン |
JP2007099988A (ja) * | 2005-10-06 | 2007-04-19 | Nissan Motor Co Ltd | 硬化型溶剤系上塗り塗料用材料、これを用いた塗料及び塗膜 |
JP4420883B2 (ja) * | 2005-10-06 | 2010-02-24 | 日産自動車株式会社 | 積層塗膜 |
SI1942163T1 (sl) | 2005-10-06 | 2012-03-30 | Nissan Motor | Material za utrdljiv material za vrhnjo prevleko na osnovi topila in prevlečni material in prevlečni film ki ga obsega ali ki je iz njega narejen |
JP2008310286A (ja) | 2007-05-14 | 2008-12-25 | Fujifilm Corp | ポリロタキサンを含有する光学フィルム、反射防止フィルム、反射防止フィルムの製造方法、偏光板、それを用いた画像表示装置 |
KR20100021454A (ko) * | 2007-06-15 | 2010-02-24 | 도꾜 다이가꾸 | 주쇄 골격이 ―Si―O―로 본질적으로 이루어지는 폴리로탁산 및 그의 제조 방법, 및 상기 폴리로탁산을 가교시켜 이루어지는 가교 폴리로탁산 및 그의 제조 방법 |
JP4911474B2 (ja) * | 2008-02-26 | 2012-04-04 | 富士フイルム株式会社 | ハードコートフィルム、偏光板、および画像表示装置 |
JP2009204727A (ja) * | 2008-02-26 | 2009-09-10 | Fujifilm Corp | ハードコートフィルム、偏光板、および画像表示装置 |
EP2174960B1 (en) * | 2008-05-07 | 2016-08-10 | Advanced Softmaterials Inc. | Polyrotaxane, crosslinked structure comprising polyrotaxane and polymer, and processes for producing these |
CN102046662B (zh) | 2008-05-30 | 2013-08-28 | 高级软质材料株式会社 | 聚轮烷、水系聚轮烷分散组合物、聚轮烷与聚合物的交联体以及它们的制造方法 |
JP5907646B2 (ja) | 2009-02-16 | 2016-04-26 | 日産自動車株式会社 | 微粒子−ポリロタキサン含有塗料、微粒子−ポリロタキサン含有塗膜及び塗装物品 |
JP2011046917A (ja) * | 2010-02-26 | 2011-03-10 | Advanced Softmaterials Inc | 光架橋性ポリロタキサン、該光架橋性ポリロタキサンを有する組成物、及び該組成物由来の架橋体、並びにこれらの製造方法 |
JP5817087B2 (ja) * | 2010-03-02 | 2015-11-18 | 日産自動車株式会社 | 修飾ポリロタキサンおよびその製造方法ならびにこれを用いた溶液、溶剤系塗料、溶剤系塗膜 |
JP5859170B2 (ja) * | 2012-05-25 | 2016-02-10 | エルジー・ケム・リミテッド | ポリロタキサン化合物、光硬化性コーティング組成物およびコーティングフィルム |
KR101379491B1 (ko) * | 2012-05-31 | 2014-04-01 | 주식회사 엘지화학 | 하드코팅 필름 및 이의 제조방법 |
KR101501686B1 (ko) * | 2012-05-31 | 2015-03-11 | 주식회사 엘지화학 | 하드코팅 필름 |
KR101418409B1 (ko) * | 2012-05-31 | 2014-07-09 | 주식회사 엘지화학 | 하드코팅 조성물 |
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KR101470463B1 (ko) * | 2012-08-23 | 2014-12-08 | 주식회사 엘지화학 | 하드코팅 필름 |
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