JP6101147B2 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
- Publication number
- JP6101147B2 JP6101147B2 JP2013105828A JP2013105828A JP6101147B2 JP 6101147 B2 JP6101147 B2 JP 6101147B2 JP 2013105828 A JP2013105828 A JP 2013105828A JP 2013105828 A JP2013105828 A JP 2013105828A JP 6101147 B2 JP6101147 B2 JP 6101147B2
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- Prior art keywords
- sensitive adhesive
- pressure
- polyol
- resin composition
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims description 97
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- 150000003077 polyols Chemical class 0.000 claims description 113
- -1 isocyanate compound Chemical class 0.000 claims description 74
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- 239000012948 isocyanate Substances 0.000 claims description 45
- 239000000463 material Substances 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 230000001070 adhesive effect Effects 0.000 claims description 25
- 239000000853 adhesive Substances 0.000 claims description 24
- 239000012790 adhesive layer Substances 0.000 claims description 18
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 27
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 24
- 238000004132 cross linking Methods 0.000 description 24
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C08G18/4277—Caprolactone and/or substituted caprolactone
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- C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4829—Polyethers containing at least three hydroxy groups
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L75/04—Polyurethanes
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
OH基を2個以上有するポリオール(A)、多官能イソシアネート化合物(B)、および触媒(C)を含む、樹脂組成物であって、
該ポリオール(A)100重量部に対する該多官能イソシアネート化合物(B)の含有割合が1重量部〜100重量部であり、
該触媒(C)が鉄錯体化合物である。
本発明の樹脂組成物は、OH基を2個以上有するポリオール(A)、多官能イソシアネート化合物(B)、および触媒(C)を含む。ポリオール(A)のOH基の数の上限は特に限定されないが、例えば、好ましくは10個以下であり、より好ましくは8個以下であり、さらに好ましくは6個以下であり、特に好ましくは4個以下である。
本発明の粘着剤組成物は、本発明の樹脂組成物を含む。本発明の粘着剤組成物中の本発明の樹脂組成物の含有割合は、好ましくは50重量%〜100重量%であり、より好ましくは70重量%〜100重量%であり、さらに好ましくは90重量%〜100重量%であり、特に好ましくは95重量%〜100重量%であり、最も好ましくは98重量%〜100重量%である。本発明の粘着剤組成物中の本発明の樹脂組成物の含有割合を上記範囲内に調整することにより、本発明の粘着剤組成物はより非常に高い反応性を示し、該粘着剤組成物を用いて粘着剤層を形成させる際にはポリオールと多官能イソシアネート化合物の架橋反応がより速やかに進行し、また、透明性のより高い粘着剤層を形成し得る。
本発明の粘着シートは、基材層の少なくとも片面に本発明の粘着剤層を有する。本発明の表面保護フィルムは、基材層の片面に本発明の粘着剤層を有する。
(1)粘着剤層の形成材料(例えば、本発明の粘着剤組成物)の溶液や熱溶融液を基材層上に塗布する方法、
(2)それに準じ、セパレーター状に塗布、形成した粘着剤層を基材層上に移着する方法、
(3)粘着剤層の形成材料(例えば、本発明の粘着剤組成物)を基材層上に押出して形成塗布する方法、
(4)基材層と粘着剤層を二層または多層にて押出しする方法、
(5)基材層上に粘着剤層を単層ラミネートする方法またはラミネート層とともに粘着剤層を二層ラミネートする方法、
(6)粘着剤層とフィルムやラミネート層等の基材層形成材料とを二層または多層ラミネートする方法、
などの、任意の適切な製造方法に準じて行うことができる。
ポリエチレンテレフタレート(PET)フィルム(厚さ=38μm)上に、配合直後の樹脂組成物からなる粘着剤組成物を塗布し、130℃で30秒間乾燥することにより溶剤を除去することによって、PETフィルム上に粘着剤層(厚さ=10μm)を形成し、その後、離型剤で表面処理した離型フィルムで覆い、50℃で12時間放置した後に室温(25℃)で1時間放置し、評価用表面保護フィルムとした。
評価用表面保護フィルムについて粘着力を測定した。すなわち、作製した評価用粘着保護フィルムを、幅20mm、長さ100mmのサイズにカットし、粘着剤層面をガラス(松浪ガラス(株)社製、商品名「青板切断品」、厚さ1.35mm、縦100mm×横100mm、縁磨)の非スズ面に、2kgローラーを転がして一往復する方法で圧着して粘着力評価用サンプルとした。この粘着力評価用サンプルを、23℃×50%RHの測定環境下に30分放置後、さらに50℃で4日間放置した後に、引張試験機を用いて、引張速度300mm/分、剥離角度180°の条件で粘着力(N/20mm)を測定した。
評価用表面保護フィルムについて、さらに50℃で4日放置した後に、ヘイズメーターHM−150(株式会社村上色彩技術研究所製)を使用し、JIS−K−7136に準拠し、ヘイズ(%)=(Td/Tt)×100(Td:拡散透過率、Tt:全光線透過率)により算出した。
離型剤で表面処理したポリエチレンテレフタレート(PET)フィルム(厚さ=38μm)上に配合直後の樹脂組成物からなる粘着剤組成物を塗布し、130℃で30秒間乾燥することにより溶剤を除去して、粘着剤層(厚さ=10μm)を形成した。その後、粘着剤層を離型剤で表面処理した離型フィルムで覆い、ゲル分率測定用サンプルを得た。
得られたゲル分率測定用サンプルを作製して4時間以内に粘着剤層をW1g(約0.1g)取出し、酢酸エチルに約25℃下で1週間浸漬した。その後、浸漬処理した粘着剤層を酢酸エチル中から取出し、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とした。
ポリオール(A)として、OH基を3個有する数平均分子量Mnが10000のポリオール(旭硝子株式会社製、プレミノールS3011)100重量部に対し、多官能イソシアネート化合物(B)として、多官能脂環族系イソシアネート化合物であるヘキサメチレンジイソシアネートの3量体(イソシアヌレート体)(日本ポリウレタン工業株式会社製、商品名:コロネートHX)9.8重量部、触媒(C)としてトリス(アセチルアセトナート)鉄(日本化学産業株式会社製、商品名:ナーセム第2鉄)0.04重量部を添加し、さらに酢酸エチルで固形分濃度が35重量%になるよう希釈後、攪拌して、樹脂組成物(1)を得た。
得られた樹脂組成物(1)を粘着剤組成物(1)とし、樹脂組成物(1)または粘着剤組成物(1)について各種評価を行った。
結果を表1に示した。
ポリオール(A)として、OH基を3個有する数平均分子量Mnが2000のポリオール(株式会社ダイセル製、プラクセルL320AL)100重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(2)を得た。
得られた樹脂組成物(2)を粘着剤組成物(2)とし、樹脂組成物(2)または粘着剤組成物(2)について各種評価を行った。
結果を表1に示した。
ポリオール(A)として、OH基を2個有する数平均分子量Mnが2000のポリオール(株式会社ダイセル製、プラクセルCD220PL)100重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(3)を得た。
得られた樹脂組成物(3)を粘着剤組成物(3)とし、樹脂組成物(3)または粘着剤組成物(3)について各種評価を行った。
結果を表1に示した。
ポリオール(A)として、OH基を2個有する数平均分子量Mnが5500のポリオール(旭硝子株式会社製、プレミノールS4006)70重量部、OH基を3個有する数平均分子量Mnが1500のポリオール(三洋化成株式会社製、サンニックスGP−1500)18重量部、OH基を4個有する数平均分子量Mnが1100のポリオール(旭電化株式会社製、EDP−1100)12重量部に対し、多官能イソシアネート化合物(B)としてトリメチロールプロパン/トリレンジイソシアネート3量体付加物(日本ポリウレタン工業株式会社製、商品名:コロネートL)40重量部、触媒(C)としてトリス(アセチルアセトナート)鉄(日本化学産業株式会社製、商品名:ナーセム第2鉄)0.04重量部を添加し、さらに酢酸エチルで固形分濃度が35重量%になるよう希釈後、攪拌して、樹脂組成物(4)を得た。
得られた樹脂組成物(4)を粘着剤組成物(4)とし、樹脂組成物(4)または粘着剤組成物(4)について各種評価を行った。
結果を表1に示した。
ポリオール(A)として、OH基を3個有する数平均分子量Mnが10000のポリオール(旭硝子株式会社製、プレミノールS3011)85重量部、OH基を3個有する数平均分子量Mnが3000のポリオール(三洋化成株式会社製、サンニックスGP−3000)12重量部、OH基を3個有する数平均分子量Mnが1000のポリオール(三洋化成株式会社製、サンニックスGP−1000)3重量部に対し、多官能イソシアネート化合物(B)として、多官能脂環族系イソシアネート化合物であるヘキサメチレンジイソシアネートの3量体(イソシアヌレート体)(日本ポリウレタン工業株式会社製、商品名:コロネートHX)15重量部、触媒(C)としてトリス(アセチルアセトナート)鉄(日本化学産業株式会社製、商品名:ナーセム第2鉄)0.04重量部を添加し、さらに酢酸エチルで固形分濃度が35重量%になるよう希釈後、攪拌して、樹脂組成物(5)を得た。
得られた樹脂組成物(5)を粘着剤組成物(5)とし、樹脂組成物(5)または粘着剤組成物(5)について各種評価を行った。
結果を表1に示した。
触媒(C)として、トリス(アセチルアセナート)アルミニウム(Al(acac)3)(川研ファインケミカル株式会社製、商品名:アルミキレートA(W))0.04重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(C1)を得た。
得られた樹脂組成物(C1)を粘着剤組成物(C1)とし、樹脂組成物(C1)または粘着剤組成物(C1)について各種評価を行った。
結果を表1に示した。
触媒(C)として、2−エチルヘキシル酸第二鉄(Fe(2eh)3)(日本化学産業株式会社製、商品名:ニッカオクチックス鉄6%(T))0.055重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(C2)を得た。
得られた樹脂組成物(C2)を粘着剤組成物(C2)とし、樹脂組成物(C2)または粘着剤組成物(C2)について各種評価を行った。
結果を表1に示した。
触媒(C)として、ナフテン酸第一鉄(Fe(nap)3)(日本化学産業株式会社製、商品名:ナフテックス鉄5%(T))0.035重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(C3)を得た。
得られた樹脂組成物(C3)を粘着剤組成物(C3)とし、樹脂組成物(C3)または粘着剤組成物(C3)について各種評価を行った。
結果を表1に示した。
触媒(C)としてジオクチルスズジラウレート(東京ファインケミカル株式会社製、商品名:エンビライザーOL−1)0.04重量部を用いた以外は、実施例1と同様に行い、樹脂組成物(C4)を得た。
得られた樹脂組成物(C4)を粘着剤組成物(C4)とし、樹脂組成物(C4)または粘着剤組成物(C4)について各種評価を行った。
結果を表1に示した。
2 粘着剤層
10 表面保護フィルム
Claims (7)
- OH基を2個以上有するポリオール(A)、多官能イソシアネート化合物(B)、および触媒(C)を含む、樹脂組成物であって、
該ポリオール(A)100重量部に対する該多官能イソシアネート化合物(B)の含有割合が1重量部〜100重量部であり、
該ポリオール(A)が、2種類以上のポリオールであって、その少なくとも1種類がOH基を2個以上有する数平均分子量Mnが3200〜20000のポリオールであり、別の少なくとも1種類がOH基を3個以上有する数平均分子量Mnが400〜3200のポリオールであり、
該ポリオール(A)が、該OH基を2個以上有する数平均分子量Mnが3200〜20000のポリオールを、50重量%以上含有し、
該触媒(C)が鉄錯体化合物である、
樹脂組成物。 - 前記触媒(C)がトリス(アセチルアセトナート)鉄である、請求項1に記載の樹脂組成物。
- 前記ポリオール(A)が、前記OH基を2個以上有する数平均分子量Mnが3200〜20000のポリオールを、67重量%以上含有する、請求項1または2に記載の樹脂組成物。
- 請求項1から3のいずれかに記載の樹脂組成物を含む、粘着剤組成物。
- 請求項4に記載の粘着剤組成物を硬化させて得られる粘着剤層。
- 基材層の少なくとも片面に請求項5に記載の粘着剤層を有する、粘着シート。
- 基材層の片面に請求項5に記載の粘着剤層を有する、表面保護フィルム。
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JP2013105828A JP6101147B2 (ja) | 2012-07-31 | 2013-05-20 | 樹脂組成物 |
TW102125988A TWI583763B (zh) | 2012-07-31 | 2013-07-19 | 樹脂組合物、黏著劑組合物、黏著劑層、黏著片及表面保護膜 |
US13/954,667 US20140039123A1 (en) | 2012-07-31 | 2013-07-30 | Resin composition, pressure-sensitive adhesive composition, pressure-sensitive adhesive layer, pressure-sensitive adhesive sheet, and surface protective film |
KR1020130090311A KR102047137B1 (ko) | 2012-07-31 | 2013-07-30 | 수지 조성물, 점착제 조성물, 점착제 층, 점착 시트, 및 표면 보호 필름 |
EP13178720.2A EP2692756A1 (en) | 2012-07-31 | 2013-07-31 | Resin composition forming a polyurethane, pressure-sensitive adhesive composition, pressure-sensitive adhesive layer, pressure-sensitive adhesive sheet, and surface protective film |
CN201310329205.XA CN103570912B (zh) | 2012-07-31 | 2013-07-31 | 树脂组合物、压敏胶粘剂组合物、压敏胶粘剂层、压敏胶粘片和表面保护膜 |
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EP3152055A4 (en) | 2014-06-06 | 2018-02-21 | 3M Innovative Properties Company | Polyurethane laminating adhesive composition |
JP6494264B2 (ja) * | 2014-12-02 | 2019-04-03 | 日東電工株式会社 | 表面保護用粘着シート |
US10611873B2 (en) | 2014-12-16 | 2020-04-07 | 3M Innovative Properties Company | Polyurethane pressure-sensitive adhesives |
WO2016118399A1 (en) | 2015-01-21 | 2016-07-28 | 3M Innovative Properties Company | Chemical resistant polyurethane adhesive |
US11629273B2 (en) | 2017-02-28 | 2023-04-18 | 3M Innovative Properties Company | Polyurethane adhesive with chemical resistant |
JP7319918B2 (ja) * | 2017-05-26 | 2023-08-02 | バンドー化学株式会社 | 表面保護フィルム |
CN110317550B (zh) * | 2019-07-23 | 2021-11-09 | 苏州赛伍应用技术股份有限公司 | 一种oled薄膜封装制程用pu保护膜及其制备方法 |
KR20230146017A (ko) * | 2021-02-19 | 2023-10-18 | 닛토덴코 가부시키가이샤 | 접착제층 및 접착제층을 갖는 광학 적층체 |
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US3314834A (en) * | 1962-12-14 | 1967-04-18 | United Aircraft Corp | Method of pot life extension for polyurethane propellants |
JPS5676426A (en) * | 1979-11-28 | 1981-06-24 | Mitui Toatsu Chem Inc | Production of polyurethane composition |
US4613660A (en) * | 1985-02-19 | 1986-09-23 | Ashland Oil, Inc. | Polyol/polyepoxide/polyurethane adhesive |
US5194112A (en) * | 1990-09-14 | 1993-03-16 | The United States Of America As Represented By The Secretary Of The Army | Method of applying a fiber optic adhesive to a fiber optic material |
US5247000A (en) * | 1990-09-14 | 1993-09-21 | The United States Of America As Represented By The Secretary Of The Army | Fiber optic adhesive |
JP2001240830A (ja) * | 2000-02-28 | 2001-09-04 | Saiden Chemical Industry Co Ltd | 粘着剤組成物および表面保護フィルム |
JP2004231878A (ja) * | 2003-01-31 | 2004-08-19 | Tosoh Corp | ポリウレタン樹脂製造用触媒組成物及びポリウレタン樹脂の製造方法 |
JP2004323680A (ja) * | 2003-04-24 | 2004-11-18 | Inoac Corp | 回転成形体およびその製造方法 |
JP2006182795A (ja) | 2004-12-24 | 2006-07-13 | Mitsubishi Chemicals Corp | ポリウレタン粘着剤組成物、及び粘着シート又は表面保護フィルム |
EP1860131A1 (de) * | 2006-05-24 | 2007-11-28 | Sika Technology AG | Katalysierungssystem |
TW200932769A (en) * | 2007-11-13 | 2009-08-01 | Toagosei Co Ltd | Curable composition and method for producing urethane (meth)acrylate |
JP5466366B2 (ja) * | 2008-01-15 | 2014-04-09 | サンスター技研株式会社 | 粘着剤組成物 |
EP2604617A1 (de) * | 2011-12-12 | 2013-06-19 | Sika Technology AG | Eisen(III)-Komplexverbindungen als Katalysatoren für Polyurethan-Zusammensetzungen |
JP6279827B2 (ja) * | 2011-12-20 | 2018-02-14 | 日東電工株式会社 | 粘着剤組成物、粘着剤層および粘着シート |
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2013
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- 2013-07-19 TW TW102125988A patent/TWI583763B/zh active
- 2013-07-30 US US13/954,667 patent/US20140039123A1/en not_active Abandoned
- 2013-07-30 KR KR1020130090311A patent/KR102047137B1/ko active IP Right Grant
- 2013-07-31 EP EP13178720.2A patent/EP2692756A1/en not_active Withdrawn
- 2013-07-31 CN CN201310329205.XA patent/CN103570912B/zh active Active
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KR20140016844A (ko) | 2014-02-10 |
JP2014043550A (ja) | 2014-03-13 |
CN103570912B (zh) | 2018-03-06 |
KR102047137B1 (ko) | 2019-11-20 |
US20140039123A1 (en) | 2014-02-06 |
TW201408744A (zh) | 2014-03-01 |
EP2692756A1 (en) | 2014-02-05 |
TWI583763B (zh) | 2017-05-21 |
CN103570912A (zh) | 2014-02-12 |
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