JP5717940B2 - 混合物の硬化促進方法および粘着剤組成物の硬化促進方法 - Google Patents
混合物の硬化促進方法および粘着剤組成物の硬化促進方法 Download PDFInfo
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- JP5717940B2 JP5717940B2 JP2006347980A JP2006347980A JP5717940B2 JP 5717940 B2 JP5717940 B2 JP 5717940B2 JP 2006347980 A JP2006347980 A JP 2006347980A JP 2006347980 A JP2006347980 A JP 2006347980A JP 5717940 B2 JP5717940 B2 JP 5717940B2
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- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- REJKHFKLPFJGAQ-UHFFFAOYSA-N oxiran-2-ylmethanethiol Chemical compound SCC1CO1 REJKHFKLPFJGAQ-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 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
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- AAYRWMCIKCRHIN-UHFFFAOYSA-N propane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CCCS(O)(=O)=O AAYRWMCIKCRHIN-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920006300 shrink film Polymers 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Description
前記カルボキシル基含有ポリマーが、モノマー単位として、一般式CH2=C(R1)COOR2(ただし、R1は水素またはメチル基、R2は炭素数2〜14のアルキル基である)で表される(メタ)アクリル系モノマー50〜99.9重量%、およびカルボキシル基含有モノマー0.1〜20重量%含有する含有する(メタ)アクリル系ポリマー(B)であることが好ましい。
各実施例・比較例で作製した粘着剤層をW1g取り出し、酢酸エチルに室温(約25℃)下で7日間浸漬した。その後、浸漬処理した粘着剤層(不溶分)を酢酸エチル中から取り出し、130℃で2時間乾燥後の重量W2gを測定し、(W2/W1)×100として計算される値をゲル分率(重量%)とした。
得られた(メタ)アクリル系ポリマーの重量平均分子量は、GPC(ゲル・パーミエーション・クロマトグラフィー)により測定した。
・分析装置:東ソー社製、HLC−8120GPC
・カラム:東ソー社製、G7000HXL+GMHXL+GMHXL
・カラムサイズ;各7.8mmφ×30cm(計90cm)
・カラム温度:40℃
・流量:0.8ml/min
・注入量:100μl
・溶離液:テトラヒドロフラン
・検出器:示差屈折計(RI)
なお、分子量はポリスチレン換算により算出した。
熱分解処理後の過酸化物分解量(mol%)は、HPLC(高速液体クロマトグラフィー)により測定した。
・装置:東ソー社製、HPL CCPM/UV8000
・カラム:MACHEREY−NAGEL社製、NUCLEOSIL 7C18(4.6mmφ×250mm)
・カラム流量:1ml/min
・カラム圧力:41kg/cm2
・カラム温度:40℃
・注入量:10μl
・溶離液:水/アセトニトリル=30/70
・注入試料濃度:0.01重量%
・検出器:UV検出器(230nm)。
実施例、比較例で得られた光学部材(幅25mm)を、無アルカリガラスに2kgローラーでロール1往復して貼着した。その後、50℃、0.5Mpaのオートクレーブにて30分間処理した後、23℃×50%RH雰囲気下において3時間放置後、剥離角度90°、剥離速度300mm/minで剥離接着力を測定した。
作製した12インチサイズの光学部材を無アルカリガラス(厚さ:0.5mm)に貼り付けた後、50℃、0.5Mpaのオートクレーブにて30分間、次いで80℃の雰囲気下で100時間保存してから、室温(約25℃)に戻し、評価用サンプルを得た。耐熱試験の評価は目視でおこない、評価基準は以下のとおりである。
・光学部材の浮きや剥がれが生じなかった場合:○
・光学部材の浮きや剥がれがかなり生じた場合:×。
各実施例・比較例で作製した粘着剤付光学部材を、エージング処理を行わずにプレス機を用いて打ち抜き加工処理を行い、上記加工処理の際の切断刃の状態を目視にて観察評価した。評価基準は以下のとおりである。
・粘着剤層の付着・破損が認められなかった場合:○
・粘着剤層の付着・破損が認められた場合:×。
ブチルアクリレート100重量部、アクリル酸0.5重量部、4−ヒドロキシブチルアクリレート0.5重量部、2,2−アゾビスイソブチロニトリル0.1重量部、および酢酸エチル200部を、窒素導入管、冷却管を備えた4つ口フラスコに投入し、充分に窒素置換した後、窒素気流下で境搾しながら55℃で15時間重合反応を行い、重量平均分子量188万の高分子量共重合体(a)を得た。
ブチルアクリレート100重量部、アクリル酸0.5重量部、4−ヒドロキシブチルアクリレート2重量部、および2,2−アゾビスイソブチロニトリル0.1重量部として、実施例1と同様に重合反応処理を行い、重量平均分子量196万の高分子量共重合体(b)を得た。
ブチルアクリレート100重量部、アクリル酸5重量部、4−ヒドロキシブチルアクリレート0.5重量部、および2,2−アゾビスイソブチロニトリル0.1重量部として、実施例1と同様に重合反応処理を行い、重量平均分子量210万の高分子量共重合体(c)を得た。
ブチルアクリレート100重量部、4−ヒドロキシブチルアクリレート1重量部、および2,2−アゾビスイソブチロニトリル0.1重量部として、実施例1と同様に重合反応処理を行い、重量平均分子量170万のカルボキシル基がない高分子量共重合体(d)を得た。
ブチルアクリレート100重量部、アクリル酸2重量部、および2,2−アゾビスイソブチロニトリル0.1重量部として、実施例1と同様に重合反応処理を行い、重量平均分子量190万の水酸基がない高分子量共重合体(e)を得た。
上記の高分子量体(d)と高分子量体(e)が固形分重量比で80:20になるように混合して、この混合物100重量部に対して、実施例1と同様にポリイソシアネート系架橋剤を配合して粘着剤組成物を調製し、塗布・乾燥・架橋を行い、ゲル分率を測定した。
実施例1の高分子量体(a)溶液の固形分100重量部に対して、トリメチロールプロパンのへキサメチレンジイソシアネート付加物からなるポリイソシアネート系架橋剤(三井化学ポリウレタン社製、タケネートD160N)0.1重量部、3−グリシドキシプロピルトリメトキシシラン0.05重量部を配合した粘着剤組成物を調製した。
実施例2の高分子量体(b)溶液を用いて、実施例5と同様の処理を行い、実施例6の粘着剤付光学フィルムとした。
実施例3の高分子量体(c)溶液を用いて、実施例5と同様の処理を行い、実施例7の粘着剤光学フィルムとした。
実施例4の高分子量体(d)および高分子量体(e)の混合物溶液を用いて、実施例5と同様の処理を行い、実施例8の粘着剤付光学フィルムとした。
比較例1の高分子量体(d)溶液を用いて、実施例5と同様の処理を行ない、比較例3の粘着剤付光学フィルムとした。
比較例2の高分子量体(e)溶液を用いて、実施例5と同様の処理を行い、比較例4の粘剤付光学フィルムとした。
実施例1の高分子量体(a)溶液の固形分100重量部に対して、ジベンゾイルパーオキシド(1分間半減期:130℃)0.3重量部、トリメチロールプロパンのへキサメチレンジイソシアネート付加物からなるポリイソシアネート系架橋剤0.06重量部(三井化学ポリウレタン社製、タケネートD160N)、ならびに3−グリシドキシプロピルトリメトキシシラン0.05重量部を配合した粘着剤組成物を調製した。
実施例2の高分子量体(b)溶液を用いて、実施例9と同様にして、実施例10の粘着剤付光フィルムとした。なお、このときの粘着剤のゲル分は88重量%で、乾燥時の過酸化物の分率は88mol%であった。
実施例3の高分子量(c)体溶液の固形分100重量部に対して、ジベンゾイルパーオキシド(1分間半減期:130℃)0.25重量部、トリメチロールプロパンのトリレンジイソシアネート付加物からなるポリイソシアネート系架橋剤0.06重量部(日本ポリウレタン社製、コロネートL)、ならびに3−グリシドキシプロピルトリメトキシシラン0.08重量部を配合した粘着剤組成物を調製した。
実施例4の高分子量体(d)および高分子量体(e)の混合物溶液の固形分100重量部に対して、ジベンゾイルパーオキシド(1分間半減期:130℃)0.30重量部、トリメチロールプロパンのトリレンジイソシアネート付加物からなるポリイソシアネート系架橋剤(日本ポリウレタン社製、コロネートL)0.08重量部、ならびに3−グリシドキシプロピルトリメトキシシラン0.08重量部を配合した粘着剤組成物を調製した。
Claims (11)
- イソシアネート系架橋剤と水酸基含有ポリマーとを含む混合物の硬化促進方法であって、前記水酸基含有ポリマーが、モノマー単位として、一般式CH2=C(R1)COOR2(ただし、R1は水素またはメチル基、R2は炭素数2〜14のアルキル基である)で表される(メタ)アクリル系モノマー50〜99.9重量%および水酸基含有モノマー0.1〜20重量%含有する(メタ)アクリル系ポリマー(A)であり、
前記混合物はさらに、モノマー単位として、一般式CH2=C(R1)COOR2(ただし、R1は水素またはメチル基、R2は炭素数2〜14のアルキル基である)で表される(メタ)アクリル系モノマー50〜99.9重量%、およびカルボキシル基含有モノマー0.1〜20重量%含有する(メタ)アクリル系ポリマー(B)を含み、
前記(メタ)アクリル系ポリマー(A)と前記(メタ)アクリル系ポリマー(B)のブレンド比率は、(メタ)アクリル系ポリマー(A)が60〜98重量%、(メタ)アクリル系ポリマー(B)が2〜40重量%であり、
前記イソシアネート系架橋剤の含有量は、前記(メタ)アクリル系ポリマー(A)および前記(メタ)アクリル系ポリマー(B)の合計量100重量部に対して0.02〜0.5重量部であり、
前記混合物はさらに、前記(メタ)アクリル系ポリマー(A)および前記(メタ)アクリル系ポリマー(B)の合計量100重量部に対して過酸化物を0.02〜2重量部含有し、
前記混合物の乾燥・架橋直後のゲル分率(a)と乾燥・架橋して23℃で7日間保存後のゲル分率(b)の差(b)−(a)を5重量%以下にする、ことを特徴とする前記混合物の硬化促進方法。 - イソシアネート系架橋剤と水酸基含有ポリマーとを含む粘着剤組成物を硬化促進させて得られる粘着剤層を光学部材の片面または両面に形成した粘着剤付光学部材であって、前記水酸基含有ポリマーが、モノマー単位として、一般式CH2=C(R1)COOR2(ただし、R1は水素またはメチル基、R2は炭素数2〜14のアルキル基である)で表される(メタ)アクリル系モノマー50〜99.8重量%、水酸基含有モノマー0.1〜20重量%、およびカルボキシル基含有モノマー0.1〜20重量%含有する(メタ)アクリル系ポリマー(C)であり、
前記イソシアネート系架橋剤の含有量は、前記(メタ)アクリル系ポリマー(C)100重量部に対して0.02〜0.5重量部であり、
前記粘着剤組成物はさらに、前記(メタ)アクリル系ポリマー(C)100重量部に対して過酸化物を0.02〜2重量部含有し、
前記粘着剤組成物の乾燥・架橋直後のゲル分率(a)と乾燥・架橋して23℃で7日間保存後のゲル分率(b)の差(b)−(a)が5重量%以下である、ことを特徴とする粘着剤付光学部材。 - 前記(メタ)アクリル系ポリマー(C)100重量部に対し、過酸化物0.05〜1重量部含有することを特徴とする請求項2に記載の粘着剤付光学部材。
- 架橋処理時の過酸化物の分解量を50重量%以上にする請求項1記載の混合物の硬化促進方法。
- 前記混合物が粘着剤組成物である請求項1又は4記載の混合物の硬化促進方法。
- 請求項1、4、又は5記載の硬化促進方法を用いて得られた混合物の硬化物。
- 請求項5に記載の硬化促進方法を用いて得られた粘着剤層。
- 前記粘着剤層のゲル分率が50〜95重量%である請求項7に記載の粘着剤層。
- 前記粘着剤層のゲル分率が50〜95重量%である請求項2又は3記載の粘着剤付光学部材。
- 請求項7又は8に記載の粘着剤層を光学部材の片面または両面に形成していることを特徴とする粘着剤付光学部材。
- 請求項2、3、9、又は10に記載の粘着剤付光学部材を少なくとも1枚用いた画像表示装置。
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