JP6275700B2 - 3重硬化型の、場合により透明な接着剤 - Google Patents
3重硬化型の、場合により透明な接着剤 Download PDFInfo
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- JP6275700B2 JP6275700B2 JP2015514341A JP2015514341A JP6275700B2 JP 6275700 B2 JP6275700 B2 JP 6275700B2 JP 2015514341 A JP2015514341 A JP 2015514341A JP 2015514341 A JP2015514341 A JP 2015514341A JP 6275700 B2 JP6275700 B2 JP 6275700B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
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- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
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- B32B38/00—Ancillary operations in connection with laminating processes
- B32B38/0008—Electrical discharge treatment, e.g. corona, plasma treatment; wave energy or particle radiation
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
- B32B2457/202—LCD, i.e. liquid crystal displays
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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Description
欠点を有する。UV硬化にかかる時間は最も短いが、UV-硬化は装置に高い要求を有し
、未硬化の接着剤が影領域に残り得る。熱硬化にかかる時間はUV硬化にかかる時間より
も長いが、熱硬化は熱に弱い精密部品の結合およびシーリングには適当でない。湿分硬化
は装置に対する要求が低いが、比較的長い硬化時間がかかる。
a)イソシアネート基および(メタ)アクリルオキシ基を有するオリゴマー;
b)イソシアネート基を有さない(メタ)アクリル酸モノマーおよび/またはオリゴマー;
c)光重合開始剤;および
d)ペルオキシド
を含む。
・約20〜約80重量%の、イソシアネート基および(メタ)アクリルオキシ基を有するオリゴマー;
・約20〜約80重量%の、イソシアネート基を有さない(メタ)アクリル酸モノマーおよび/またはオリゴマー;
・約0.1〜約3.0重量%の光重合開始剤;
・約0〜約3重量%の有機金属触媒;および
・約0.1〜約3重量%のペルオキシド
を含む。
接着剤組成物中の成分の総重量%は合計して100重量%である。
・本発明の接着剤組成物でコートされた結合またはシールする領域にUV光を照射する;
・熱硬化条件下に結合またはシールする部品を置く;および/または
・湿分硬化条件下に結合またはシールする部品を置く。
a)イソシアネート基および(メタ)アクリルオキシ基を有するオリゴマー;
b)イソシアネート基を有さない(メタ)アクリル酸モノマーおよび/またはオリゴマー;
c)光重合開始剤;および
d)ペルオキシド。
本発明に使用されるイソシアネート基および(メタ)アクリルオキシ基を有するオリゴマーは、例えば、脂肪族ウレタンオリゴマー、ポリエステルオリゴマー、ポリエーテルオリゴマー、エポキシオリゴマー等またはそれらの組合せであり得る。
ゴマー>
本発明の接着剤組成物は、(メタ)アクリル酸、(メタ)アクリレートおよび(メタ)
アクリルアミドから選択されるモノマーをさらに含む。成分a)のイソシアネート基を有
する(メタ)アクリル酸モノマーとの違いとして、成分b)の(メタ)アクリル酸モノマ
ーはイソシアネート基を含有しない。該モノマー分子は不飽和(メタ)アクリル基を有し
、光照射を施す際に硬化反応を受け得る。これらのモノマーは常温で比較的低い粘性を有するため、該モノマーを接着剤組成物の粘度および接着性を調整するために使用することもでき、これらは、接着剤組成物の透明性を調整し、該組成物の貯蔵安定性を改善することもできる。
光重合開始剤は、成分a)、b)およびc)の光重合を開始するために使用され、接着剤組成物の光硬化速度を高める。本発明の接着剤組成物は、好ましくはフリーラジカル光重合開始剤を含有する。
本発明の接着剤は、熱開始剤として有機ペルオキシドを含む。有機ペルオキシドは、ペルオキシジカーボネート、例えばジ(2-エチルヘキシル)ペルオキシジカーボネート;アシルペルオキシド、例えばラウロイルペルオキシド;アルキルペルオキシド、例えば2,5-ジメチル-2,5-ジ(tert-ブチルペルオキシ)ヘキサン;ペルオキシエステル、例えばtert-ブチルペルオキシベンゾエート;等であり得る。
有機金属触媒は、湿分硬化型反応を引き起こし促進するために本発明の接着剤に含まれ得る。有機金属触媒の具体的な添加量は、実現すべき生成物の特性に応じて調整してよく、場合により、添加量はゼロであり得る。
上記に述べた成分の他に、本発明の接着剤組成物は他の助剤、例えば光安定剤、熱安定剤、光開始促進剤、熱開始促進剤、レべリング剤、強化剤、増粘剤等をも含み得る。
本発明の接着剤を、シールする領域または結合させる基材に、当業者に既知の常套法により適用し得る。本発明の接着剤は、ガラス基材およびプラスチック基材に対して優れた結合作用を有する。
Desmolux D 100(Bayer, AG)
CN9021(Sartomer Chemical Ltd.)
Desmolux VP LS 2396(Bayer, AG)
本発明の接着剤組成物の優れた特性を試験するために、UV硬化性、湿分硬化性、熱硬化性、接着強度および透過率の特性を測定試験した。
UV硬化性試験は、室温で、約3000mJ/cm2の放射エネルギーを有するUV光源(Loctite UVALOC 1000、Henkel AG)を用いて約200nm〜約400nmの波長で行った。例えば、各接着剤組成物への照射を、約30秒またはそれ以上で、約100mW/cm2の放射電力で行った。
接着剤組成物を用いて結合後、恒温(23±2℃)および一定湿度(50±10%RH)で、完全に光のない室内に試料をおいた。完全に光がないことを確保するために、試料をアルミニウム箔で覆ってもよい。所定の目標時間によって、湿分硬化の結果を確認した。
ガラスおよびポリカーボネート(PC)間の接着剤組成物について、200℃以上の最高温度を有する温度調整可能オーブン中、光のない条件下で、熱硬化性試験を行った。特定の硬化温度および時間は、接着剤組成物の具体的組成による。
接着強度は、完全に硬化した接着剤組成物によりもたらされる2つの基材間の結合強度を特徴づけるために用いられる。通常、硬化層の厚みは要求に応じて約100μmであった。基材はガラスプレート、PMMAプレートおよびポリエステルプレートから選択した。試験のための装置は、ユニバーサル引張試験機(Instron 5569、Instron Inc.)であった。この試験中、互いに結合した2つの試料プレートを反対方向に引き離した。接着強度(MPa)は、試験される力の値を結合領域で割ることにより得た。
可視光領域における硬化接着剤組成物の透過率を、UVおよび可視光分光光度計により試験した。接着剤組成物の硬化厚みは、2つのガラス層により約100μmに調整した。試験法は、ASTM D1005-2007に準じる。該試験法に従い、2つのガラスプレート間の接着剤組成物を100mW/cm2の放射電力を有するUV光で30秒間照射し、硬化接着剤組成物の透過率を測定した。
実施例1
室温で、50.75重量部のDesmolux D 100、45重量部のイソボルニルアクリレートおよび2重量部の2-ヒドロキシル-2-メチル-1-フェニル-1-アセトンを撹拌を行うための撹拌タンク中に別々に計り入れ、撹拌速度を約60rpmに設定し、撹拌時間を約60分とした。続いて、1重量部の(2,4,6-トリメチルベンゾイル)-ジフェニル-ホスフィンオキシド、0.25重量部のジブチル錫ジラウレートおよび2重量部の1,1-ジtert-ブチルペルオキシ-3,3,5-トリメチル-シクロヘキサンを該撹拌タンク中に別々に計り入れ、撹拌速度を約100rpmに設定し、撹拌をさらに約60分行った。全ての成分を均一に混合後、該混合物をろ過した。供給および混合の全工程において、光を遮るように保ち、一定温度を保った。
Claims (9)
- a)イソシアネート基および(メタ)アクリルオキシ基を有するオリゴマー;
b)イソシアネート基を有さない(メタ)アクリル酸モノマーおよび/またはオリゴマー;
c)光重合開始剤;
d)ペルオキシド;および
e)有機金属触媒
を含む、接着剤組成物。 - 前記成分a)はイソシアネート基および(メタ)アクリルオキシ基を有する脂肪族ウレタンである、請求項1に記載の接着剤組成物。
- 前記成分b)は脂肪族(メタ)アクリレートモノマーである、請求項1または2に記載の接着剤組成物。
- 前記光重合開始剤はヒドロキシケトン開始剤およびアシルホスフィンペルオキシド開始剤から選択される、請求項1〜3のいずれかに記載の接着剤組成物。
- 前記ペルオキシドはペルオキシエステルおよびアルキルペルオキシドから選択される、請求項1〜4のいずれかに記載の接着剤組成物。
- 前記有機金属触媒は第一錫オクトアート、ジブチル錫ジラウレートおよびジブチル錫ジアセテートから選択される1種以上の有機錫触媒である、請求項1に記載の接着剤組成物。
- 20重量%〜80重量%のイソシアネート基および(メタ)アクリルオキシ基を有するオリゴマー;
20重量%〜80重量%のイソシアネート基を有さない(メタ)アクリル酸モノマーおよび/またはオリゴマー;
0.1重量%〜3.0重量%の光重合開始剤;
0.1重量%〜3.0重量%の有機金属触媒;および
0.1重量%〜3.0重量%のペルオキシド;
を含み、接着剤組成物中の成分の総重量%は合計して100重量%である、請求項1に記載の接着剤組成物。 - 請求項1〜7のいずれかに記載の接着剤組成物を使用する結合およびシーリング方法であって、該方法は以下:
本発明の接着剤組成物でコートされた結合またはシールする領域に、UV光を照射すること;
結合またはシールする部品を熱硬化条件下に置くこと;および/または
結合またはシールする部品を湿分硬化条件下に置くこと
を含む、方法。 - 請求項1〜7のいずれかに記載の接着剤組成物が使用される液晶ディスプレイ製品。
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CN201210179477.1A CN103450817B (zh) | 2012-06-01 | 2012-06-01 | 粘合剂组合物 |
CN201210179477.1 | 2012-06-01 | ||
PCT/CN2013/076469 WO2013178077A1 (en) | 2012-06-01 | 2013-05-30 | Triply Curable Optically Clear Adhesive |
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JP2015521226A5 JP2015521226A5 (ja) | 2016-04-28 |
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EP (1) | EP2855616B1 (ja) |
JP (1) | JP6275700B2 (ja) |
KR (1) | KR20150023538A (ja) |
CN (2) | CN103450817B (ja) |
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WO (1) | WO2013178077A1 (ja) |
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CN103450817B (zh) * | 2012-06-01 | 2017-07-04 | 汉高股份有限公司 | 粘合剂组合物 |
CN105593247A (zh) * | 2014-01-21 | 2016-05-18 | 积水化学工业株式会社 | 光湿气固化型树脂组合物、电子部件用粘接剂和显示元件用粘接剂 |
WO2015182697A1 (ja) * | 2014-05-30 | 2015-12-03 | 積水化学工業株式会社 | 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 |
CN104531046A (zh) * | 2015-02-02 | 2015-04-22 | 朱建国 | 胶粘剂组合物及其使用方法和用途 |
KR102036278B1 (ko) | 2015-07-21 | 2019-10-25 | 주식회사 엘지화학 | 광학용 점착제 조성물 및 광학용 점착 필름 |
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JP2009197053A (ja) * | 2008-02-19 | 2009-09-03 | Hitachi Kasei Polymer Co Ltd | 1液湿気硬化型ウレタン樹脂接着剤組成物 |
JP2011190421A (ja) * | 2010-03-17 | 2011-09-29 | Hitachi Kasei Polymer Co Ltd | 活性エネルギー線硬化型接着剤組成物 |
KR101142804B1 (ko) * | 2010-03-19 | 2012-05-08 | 주식회사 신광화학산업 | 자외선 경화형 폴리우레탄 접착제의 제조방법 |
KR101279975B1 (ko) * | 2010-10-05 | 2013-07-05 | 제일모직주식회사 | 도체간 전기적 접속 재료 |
CN103450817B (zh) | 2012-06-01 | 2017-07-04 | 汉高股份有限公司 | 粘合剂组合物 |
US8926851B2 (en) * | 2012-11-18 | 2015-01-06 | HGST Netherlands B.V. | Method for making a film of uniformly arranged core-shell nanoparticles on a substrate |
-
2012
- 2012-06-01 CN CN201210179477.1A patent/CN103450817B/zh active Active
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2013
- 2013-05-30 EP EP13797350.9A patent/EP2855616B1/en not_active Not-in-force
- 2013-05-30 WO PCT/CN2013/076469 patent/WO2013178077A1/en active Application Filing
- 2013-05-30 JP JP2015514341A patent/JP6275700B2/ja active Active
- 2013-05-30 CN CN201380027804.4A patent/CN104797675B/zh active Active
- 2013-05-30 KR KR1020147036896A patent/KR20150023538A/ko not_active Application Discontinuation
- 2013-05-31 TW TW102119262A patent/TWI596181B/zh not_active IP Right Cessation
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EP2855616B1 (en) | 2017-04-26 |
CN103450817B (zh) | 2017-07-04 |
CN104797675B (zh) | 2017-05-31 |
US9783710B2 (en) | 2017-10-10 |
CN104797675A (zh) | 2015-07-22 |
TW201406905A (zh) | 2014-02-16 |
EP2855616A1 (en) | 2015-04-08 |
US20150083317A1 (en) | 2015-03-26 |
JP2015521226A (ja) | 2015-07-27 |
KR20150023538A (ko) | 2015-03-05 |
EP2855616A4 (en) | 2016-01-27 |
CN103450817A (zh) | 2013-12-18 |
TWI596181B (zh) | 2017-08-21 |
WO2013178077A1 (en) | 2013-12-05 |
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