CN102746801B - 电化学装置用粘合带 - Google Patents
电化学装置用粘合带 Download PDFInfo
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- CN102746801B CN102746801B CN201110221390.1A CN201110221390A CN102746801B CN 102746801 B CN102746801 B CN 102746801B CN 201110221390 A CN201110221390 A CN 201110221390A CN 102746801 B CN102746801 B CN 102746801B
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- Prior art keywords
- methyl
- weight
- adhesive tape
- alkyl
- monomer
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- 239000002390 adhesive tape Substances 0.000 title claims abstract description 62
- 239000000178 monomer Substances 0.000 claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 44
- 239000011230 binding agent Substances 0.000 claims abstract description 41
- 229920002125 Sokalan® Polymers 0.000 claims abstract description 29
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 239000003522 acrylic cement Substances 0.000 claims abstract description 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 15
- 229920003023 plastic Polymers 0.000 claims abstract description 7
- 239000004033 plastic Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 (methyl) vinylformic acid ester Chemical class 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 47
- 238000000034 method Methods 0.000 description 20
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- 150000001875 compounds Chemical class 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 238000006073 displacement reaction Methods 0.000 description 10
- 229910001416 lithium ion Inorganic materials 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 9
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- 239000004814 polyurethane Substances 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000007598 dipping method Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
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- 229920002554 vinyl polymer Polymers 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 7
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- 230000000052 comparative effect Effects 0.000 description 7
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- 238000004804 winding Methods 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
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- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
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- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
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- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
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- WQUYGVLLSSYSRD-UHFFFAOYSA-N C(C=C)(=O)OCC(C)O.CC=CC(=O)O Chemical compound C(C=C)(=O)OCC(C)O.CC=CC(=O)O WQUYGVLLSSYSRD-UHFFFAOYSA-N 0.000 description 1
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- YUIVHZARNDKOHO-UHFFFAOYSA-N n-tert-butyl-n-methylprop-2-enamide Chemical compound CC(C)(C)N(C)C(=O)C=C YUIVHZARNDKOHO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一种电化学装置用粘合带,其水分的含量极低,不容易发生“粘合剂渗出”,且即使与电解液接触也不会剥脱。本发明的电化学装置用粘合带的特征在于,其在塑料系基材的至少一面具有由丙烯酸系粘合剂形成的粘合剂层,其具有凝胶率为60%以上、厚度为1~15μm的粘合剂层,且在23℃下、在水中浸渍24小时之后的吸水率为0.2%以下。所述丙烯酸系粘合剂优选含有如下的丙烯酸系聚合物:其是至少包含含有碳数6~10的烷基的(甲基)丙烯酸烷基酯和含异氰酸酯反应性基团单体的单体成分的共聚物,且所述单体成分的80重量%以上为所述含有碳数6~10的烷基的(甲基)丙烯酸烷基酯。
Description
技术领域
本发明涉及电化学装置用粘合带,尤其涉及在电解电容器、锂离子电池等的组装中在与电解液接触的部分或有可能与电解液接触的部分使用的粘合带。
背景技术
电化学装置在其制造工序中多使用粘合带。例如,锂离子电池在其制造工序中,在防止由异物、毛边等引起的隔离膜被贯穿、防止活性物质剥脱、在将电极板与隔离膜等的层叠体卷绕而装到电池壳体内时固定卷的尾部等各种用途中使用粘合带。
尤其对于在锂离子电池内部等有可能接触电解液的部分贴合的粘合带,要求具有即使在电解液中浸渍也能保持被粘物的优异粘接性,为了提高粘合带的粘接性而加厚粘合剂层时,粘合剂会变得容易从端面渗出,即容易发生“粘合剂渗出”,在卷绕电极板与隔离膜的层叠体时,存在所渗出的粘接剂会贴附在相对的隔离膜上等难以进行卷绕操作的问题。
另外,近年来,期望提高电化学装置的容量,为此而期望将粘合带的厚度减小至极薄。然而,减小粘合剂层的厚度时,虽不容易发生上述“粘合剂渗出”,但存在粘接性方面会变得不充分的问题。这是因为,粘合带在电解液中剥脱时,活性物质会脱落,进而由于溶出到电解液中的粘合成分与电解质反应而使得电解液特性降低、电池特性降低(专利文献1等)。
此外,粘合带主要由基材和粘合剂构成,但已知的是,通常的粘合带在基材和粘合剂层中吸收并保有空气中的水分,将这种粘合带用于电化学装置时,会由于基材和粘合剂层中保有的水分放出到电解液中而使电化学装置发生缺陷。尤其,锂离子电池的电解液中的锂盐的反应性高,会立即将放出到电解液中的水分还原分解,因此会引起电池的内压上升、电池部件的腐蚀等,电池特性容易降低。
即,现状是,尚未发现不容易发生“粘合剂渗出”、粘接性优异且水分的含量极低的电化学装置用粘合带。
现有技术文献
专利文献
专利文献1:日本特开平11-176476号公报
发明内容
发明要解决的问题
因此,本发明的目的在于提供一种电化学装置用粘合带,其水分的含量极低,不容易发生“粘合剂渗出”,且即使与电解液接触也不会剥脱。
用于解决问题的方案
本发明人等为了解决上述问题而进行了深入研究,结果发现:具有由丙烯酸系粘合剂形成的、凝胶率和厚度在特定范围内的粘合剂层的粘合带不容易发生“粘合剂渗出”、且粘接性优异;使用吸水率极低的粘合带时,可以防止由于粘合带自身所含有的水分引起的电化学装置的缺陷的发生;兼具这些特征的粘合带作为电化学装置用是极为有用的。本发明是基于这些认识而完成的。
即,本发明提供一种电化学装置用粘合带,其在塑料系基材的至少一面具有由丙烯酸系粘合剂形成的粘合剂层,其具有凝胶率为60%以上、厚度为1~15μm的粘合剂层,且在23℃下、在水中浸渍24小时之后的吸水率为0.2%以下。
作为丙烯酸系粘合剂,优选含有如下的丙烯酸系聚合物:其是将至少包含含有碳数6~10的烷基的(甲基)丙烯酸烷基酯和含异氰酸酯反应性基团单体的单体成分聚合而得到的,且所述单体成分的80重量%以上为所述含有碳数6~10的烷基的(甲基)丙烯酸烷基酯。
作为所述异氰酸酯反应性基团,优选为羟基或羧基。
构成丙烯酸系聚合物的单体成分的1~10重量%优选为含异氰酸酯反应性基团单体。
作为含有碳数6~10的烷基的(甲基)丙烯酸烷基酯,优选为选自(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸异辛酯和(甲基)丙烯酸壬酯中的一种以上物质。
发明的效果
本发明的电化学装置用粘合带不容易发生“粘合剂渗出”,且即使浸渍在电解液中也能维持优异的粘接性,即使在电解液中也能持续地保持被粘物。进而,由于吸水率低、粘合带自身的水分含量极低,因此即使贴合在电化学装置上使用,也不会因水分而引起电化学装置的缺陷。因此,在电化学装置用途、尤其在锂离子电池的制造中,可以应用于在电解液中浸渍的部位或有可能与电解液接触的部位来抑制电解液劣化、电池的内压上升以及电池部件腐蚀等缺陷的发生,并且防止由异物、毛边等引起的隔离膜被贯穿,防止活性物质剥脱,改善将电极装到电池壳体内的适应性。
附图说明
图1是示出本发明的电化学装置用粘合带的一个例子的剖面示意图。
图2是示出本发明的电化学装置用粘合带的另一个例子的剖面示意图。
图3是示出锂离子电池中的本发明的电化学装置用粘合带的使用例的示意图,图(3-1)为使用前的图,图(3-2)为将本发明的电化学装置用粘合带贴合于极板等上的图,图(3-3)为将极板卷绕并使用本发明的电化学装置用粘合带来固定卷绕的图。
附图标记说明
1 基材
2、21、22 粘合剂层
3、31、32 电化学装置用粘合带
4 电极端子
5 正极板
6 负极板
7 隔离膜
8 活性物质
具体实施方式
以下,根据需要参照附图来详细说明本发明的实施方式。
图1是示出本发明的电化学装置用粘合带的一个例子的剖面示意图,电化学装置用粘合带31具有在基材1的单面层叠有粘合剂层2的结构。
图2是示出本发明的电化学装置用粘合带的另一个例子的剖面示意图,电化学装置用粘合带32具有在基材1的一面层叠有粘合剂层21、在另一面层叠有粘合剂层22的结构。
粘合剂层
本发明的粘合剂层的特征在于由丙烯酸系粘合剂形成。所述丙烯酸系粘合剂至少含有丙烯酸系聚合物作为基础聚合物。
作为构成丙烯酸系聚合物的单体成分,相对于构成丙烯酸系聚合物的单体成分总量(100重量%),优选包含80重量%以上(优选为90重量%以上、特别优选为95重量%以上)的含有碳数6~10的烷基的(甲基)丙烯酸烷基酯。另外,相对于构成丙烯酸系聚合物的单体成分总量(100重量%),含有碳数5以下且碳数11以上的烷基的(甲基)丙烯酸烷基酯的含量优选低于20重量%(更优选低于5重量%、特别优选低于0.1重量%、最优选为0重量%)。由于碳数5以下的烷基具有亲水性,因此具有碳数5以下的烷基的(甲基)丙烯酸烷基酯相对于构成丙烯酸系聚合物的单体成分总量(100重量%)的比例过大时,存在会变得容易吸水、容易因水分而引起电化学装置的缺陷的倾向。而且,还存在Tg增高、初始粘接特性降低的倾向。另外,含有碳数11以上的烷基的(甲基)丙烯酸烷基酯相对于构成丙烯酸系聚合物的单体成分总量(100重量%)的比例过大时,粘合剂会变得过软,变得容易发生“粘合剂渗出”,而且还存在粘接性降低的倾向。
作为上述含有碳数6~10的烷基的(甲基)丙烯酸烷基酯,例如可列举出(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸2-乙基己酯(2-EHA)、(甲基)丙烯酸异辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸异壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸异癸酯等具有碳数6~10的直链或支链烷基的(甲基)丙烯酸烷基酯。此外,在本说明书中,“(甲基)丙烯酸”是指“丙烯酸”和/或“甲基丙烯酸”。
作为本发明的丙烯酸系聚合物,优选为以含有碳数6~10的烷基的(甲基)丙烯酸烷基酯为主要单体、将前述主要单体与用于改善粘接性的含官能团单体聚合而得到的聚合物(共聚物)。
作为上述含官能团单体,例如可列举出(甲基)丙烯酸、衣康酸、马来酸、富马酸、巴豆酸、异巴豆酸等含羧基单体(还包括马来酸酐、衣康酸酐等含酸酐基单体);(甲基)丙烯酸2-羟乙酯、(甲基)丙烯酸2-羟丙酯、(甲基)丙烯酸3-羟丙酯、(甲基)丙烯酸4-羟丁酯、(甲基)丙烯酸6-羟己酯等(甲基)丙烯酸羟烷基酯、乙烯醇、烯丙醇等含羟基(hydroxyl)单体;(甲基)丙烯酰胺等含酰胺基单体;N-甲基(甲基)丙烯酰胺、N-乙基(甲基)丙烯酰胺、N,N-二甲基(甲基)丙烯酰胺、N-叔丁基(甲基)丙烯酰胺、N-羟甲基(甲基)丙烯酰胺、N-甲氧基甲基(甲基)丙烯酰胺、N-乙氧基甲基(甲基)丙烯酰胺、N-丁氧基甲基(甲基)丙烯酰胺、N-辛基丙烯酰胺、N-羟乙基丙烯酰胺等含N-取代酰胺基单体;(甲基)丙烯酸氨基乙酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸二乙基氨基乙酯、(甲基)丙烯酸二甲基氨基丙酯、(甲基)丙烯酸叔丁基氨基乙酯等含氨基单体;(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸甲基缩水甘油酯等含缩水甘油基单体等。在上述含官能团单体中,在于电解液中的粘接保持性优异方面,含羧基单体和含羟基(hydroxyl)单体是优选的,在初始粘接性优异方面,含羧基单体[例如丙烯酸(AA)]是特别优选的。
相对于构成丙烯酸系聚合物的单体成分总量(100重量%),上述含官能团单体的含量例如为1~10重量%左右(尤其为1~7重量%左右、特别为1~5重量%左右)。含官能团单体的含量低于上述范围时,存在凝胶率降低而难以获得充分的粘接性的倾向。另一方面,含官能团单体的含量高于上述范围时,存在吸水率上升而难以防止由水分引起的电化学装置的缺陷的倾向。
本发明的丙烯酸系聚合物可以通过公知或惯用的聚合方法将上述单体成分聚合来制备,例如可列举出溶液聚合方法、乳液聚合方法、本体聚合法、利用活性能量射线照射的聚合方法(活性能量射线聚合方法)等。在上述当中,在能够形成透明性和耐水性优异的聚合物且廉价等方面,溶液聚合方法、活性能量射线聚合方法是优选的,更优选溶液聚合方法。
在上述溶液聚合时,可以使用各种普通溶剂。作为这种溶剂,例如可列举出醋酸乙酯、醋酸正丁酯等酯类;甲苯、苯等芳香族烃类;正己烷、正庚烷等脂肪族烃类;环己烷、甲基环己烷等脂环式烃类;甲乙酮、甲基异丁基酮等酮类等的有机溶剂。这些可以单独使用或者将两种以上组合使用。
在上述单体成分聚合时,可以使用聚合引发剂。对前述聚合引发剂没有特别限定,可以从公知或惯用的物质中适当选择来使用,例如可列举出2,2’-偶氮二异丁腈(AIBN)、2,2’-偶氮双(4-甲氧基-2,4-二甲基戊腈)、2,2’-偶氮双(2,4-二甲基戊腈)、2,2’-偶氮双(2-甲基丁腈)、1,1’-偶氮双(环己-1-腈)、2,2’-偶氮双(2,4,4-三甲基戊烷)、二甲基-2,2’-偶氮双(2-甲基丙酸酯)等偶氮系聚合引发剂;过氧化苯甲酰、叔丁基氢过氧化物、二叔丁基过氧化物、过氧苯甲酸叔丁酯、过氧化二枯基、1,1-双(叔丁基过氧)-3,3,5-三甲基环己烷、1,1-双(叔丁基过氧)环十二烷等过氧化物系聚合引发剂等油溶性聚合引发剂等。这些可以单独使用或者将两种以上组合使用。对聚合引发剂的用量没有特别限定,为迄今作为聚合引发剂可利用的范围即可。
作为本发明的丙烯酸系聚合物的分子量,例如重均分子量(Mw)为300000~1200000左右,优选为400000~1000000左右。重均分子量低于300000时,存在无法得到作为粘合剂层所需的粘合力、内聚力、耐久性变差的倾向。另一方面,重均分子量超过1200000时,有时会产生由粘合剂组合物的粘度上升引起的涂布性不良等问题。
其中,重均分子量(Mw)可以通过凝胶渗透色谱(GPC)法来测定。更具体而言,可以使用商品名“HL C-8120GPC”(Tosoh Corporation制造)作为GPC测定装置,通过聚苯乙烯换算值,在下述GPC测定条件下进行测定来求出重均分子量。
GPC的测定条件
样品浓度:0.2重量%(四氢呋喃溶液)
样品注入量:10μL
洗脱液:四氢呋喃(THF)
流量(流速):0.6mL/min
v柱温度(测定温度):40℃
柱:商品名“TSKgelSuperHM-H/H4000/H3000/H2000”(Tosoh Corporation制造)
检测器:差示折射计(RI)
进而,本发明的丙烯酸系聚合物优选通过适当的交联手段(例如交联剂的添加等)来实施交联处理。通过实施交联处理,可以调节粘合剂层的凝胶率。
作为前述交联剂,例如可列举出环氧系化合物、异氰酸酯系化合物、金属螯合化合物、金属醇盐、金属盐、胺化合物、肼化合物、醛系化合物等。这些可以根据丙烯酸系聚合物所含有的官能团适当选择来使用。在本发明中,在与塑料系基材的锚固性优异的方面,使用异氰酸酯系化合物是尤其优选的。
作为异氰酸酯系化合物,例如可列举出二官能性异氰酸酯系化合物、三官能性异氰酸酯系化合物等多官能性异氰酸酯系化合物。作为二官能性异氰酸酯系化合物,例如可列举出亚丁基二异氰酸酯、六亚甲基二异氰酸酯等低级脂肪族二异氰酸酯类;亚环戊基二异氰酸酯、亚环己基二异氰酸酯、异佛尔酮二异氰酸酯等脂环族二异氰酸酯类;2,4-甲苯二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯、苯二甲基二异氰酸酯等芳香族二异氰酸酯类等。作为三官能性异氰酸酯系化合物,例如可列举出三羟甲基丙烷/甲苯二异氰酸酯三聚体加成物(商品名“CORONATE L”,日本聚氨酯工业公司制造)、三羟甲基丙烷/六亚甲基二异氰酸酯三聚体加成物(商品名“CORONATE HL”,日本聚氨酯工业公司制造)、六亚甲基二异氰酸酯的异氰脲酸酯(商品名“CORONATE HX”,日本聚氨酯工业公司制造)等三官能性异氰酸酯加成物等。这些可以单独使用或者将两种以上组合使用。
作为本发明的交联剂,三官能性异氰酸酯系化合物在反应性优异、能更快速地固化方面是尤其优选的。
作为前述交联剂的用量,相对于100重量份上述丙烯酸系聚合物,例如为0.01~20重量份左右,优选为0.1~15重量份左右,特别优选为1~10重量份左右。交联剂的用量低于上述范围时,存在凝胶率降低而无法得到充分的聚集且难以获得粘接性的倾向,另一方面,交联剂的用量高于上述范围时,存在粘合剂变硬、粘接性降低的倾向。
本发明的丙烯酸系粘合剂除了上述丙烯酸系聚合物、交联剂以外还可以含有其他成分(例如赋粘剂、增塑剂、填充剂、抗氧化剂等)。
本发明的粘合剂层可以如下形成:根据需要使用溶剂(例如甲苯、二甲苯、醋酸乙酯、甲乙酮等)将上述丙烯酸系粘合剂稀释来制备涂布液,将该涂布液直接涂布在基材上或适当的隔离膜(剥离纸等)上、干燥,从而形成。本发明的粘合剂层可以是单层,也可以是2层以上的层叠体。在粘合剂层为2层以上的层叠体时,各层可以具有相同的组成,也可以将不同组成的层组合层叠。另外,在基材的两面具有粘合剂层时,这些粘合剂层可以具有相同的组成,也可以具有不同的组成。
本发明的粘合剂层的凝胶率为60%以上(优选为65%以上)。其中,在本发明中,凝胶率表示将粘合剂层在醋酸乙酯中浸渍了一定时间时,未溶出而残留的成分相对于粘合剂层(100重量%)的比例(重量%)。凝胶率低于上述范围时,粘合剂的内聚力会降低,会变得容易发生“粘合剂渗出”,有可能会溶解在电化学装置所使用的电解质中、粘接性降低、对电化学装置产生不良影响。
本发明的粘合剂层的厚度(在为2层以上的层叠体时,是其总厚度)为1~15μm(优选为1~10μm)。粘合剂层的厚度低于上述范围时,存在粘接力降低、在电解液中粘合带剥脱而构成引起电解液劣化的原因的倾向。另一方面,粘合剂层的厚度高于上述范围时,存在于电化学装置内所占的体积过大、难以应对电化学装置的高容量化的倾向。另外,存在难以防止“粘合剂渗出”的倾向。
基材
作为基材,优选使用吸水率低的基材,在本发明中,其特征在于使用塑料系基材。作为塑料系基材的原料,例如可列举出聚酯(聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚萘二甲酸丁二醇酯等),聚烯烃(聚乙烯、聚丙烯、聚甲基戊烯、乙烯-丙烯共聚物等),聚乙烯醇,聚偏二氯乙烯,聚氯乙烯,氯乙烯-醋酸乙烯酯共聚物,聚醋酸乙烯酯,聚酰胺,聚酰亚胺,纤维素类,氟系树脂,聚醚,聚醚酰胺,聚醚腈,聚醚醚酮,聚苯硫醚,聚苯乙烯系树脂(聚苯乙烯等),聚碳酸酯,聚醚砜等。这些可以单独使用或者将两种以上组合使用。
在本发明中,在耐热性优异方面,以选自聚对苯二甲酸乙二醇酯等聚酯、聚丙烯等聚烯烃等和氟系树脂中的树脂为原料的基材是尤其优选的,在吸水率低方面,特别优选使用以聚丙烯等聚烯烃为原料的基材。
本发明的基材可以是单层,也可以是2层以上的层叠体。在基材为2层以上的层叠体时,各层可以具有相同的组成,也可以将不同组成的层组合层叠。
另外,对于基材的表面,根据需要,为了提高与粘合剂层等的密合性,可以实施惯用的表面处理,例如铬酸处理、臭氧暴露、火焰暴露、高压电击暴露、电离辐射处理等基于化学或物理方法的氧化处理等。
对基材的厚度没有特别限定,优选为8~100μm左右,更优选为10~50μm左右。基材的厚度低于上述范围时,有可能粘合带的强度不足、损害实用性。另一方面,基材的厚度高于上述范围时,存在于电化学装置内所占的体积变得过大、难以应对电化学装置的高容量化的倾向。
电化学装置用粘合带
本发明的电化学装置用粘合带在上述基材的至少一面具有上述粘合剂层。本发明的电化学装置用粘合带可以通过公知惯用的方法来形成,例如可列举出以下方法:根据需要使用溶剂(例如甲苯、二甲苯、醋酸乙酯、甲乙酮等)将构成上述粘合剂层的丙烯酸系粘合剂稀释来制备涂布液、将该涂布液直接涂布于基材上来形成粘合剂层的方法;将前述涂布液涂布在适当的隔离膜(剥离纸等)上来形成粘合剂层、将该粘合剂层转印(转移)到基材上的方法等。在利用转印时,粘合剂层与基材的界面有可能残留空隙(void)。在该情况下,可以通过高压釜处理等来实施加温加压处理而使空隙扩散、消失。
前述涂布液的涂布可以使用惯用的涂布机,例如照相凹版辊涂布机、逆转辊涂布机、辊舔涂布机、浸入辊式涂布机(diproll coater)、棒涂布机、刮刀涂布机、喷雾涂布机、逗点涂布机(comma coater)、直接涂布机等。
另外,本发明的电化学装置用粘合带也可以用将基材原料和上述丙烯酸系粘合剂熔融挤出来使之一体化的方法来形成。作为熔融挤出方法,可以使用吹胀法、T形模头法等任意的公知技术。另外,挤出成型之后,可以实施沿纵向或横向的拉伸(单轴拉伸)处理、纵向和横向上的依次或同时拉伸(双轴拉伸)处理等。
本发明的电化学装置用粘合带例如可以通过对被粘物用0.5~10kg/cm2左右的压力进行按压来贴合。对按压时的温度没有特别限定,例如为10~180℃左右。
对于按压后的粘接力(相对于铝箔),例如在25℃下的对铝箔的180°剥离粘合力(依据JIS Z0237,相对于铝箔,剥离速度:300mm/分钟:浸渍前粘接力)为0.5N/10mm以上(优选为1.0N/10mm以上,特别优选为1.05~2.5N/10mm)左右。
另外,对于本发明的电化学装置用粘合带在碳酸亚乙酯/碳酸二乙酯混合溶剂[前者/后者(体积比)=1/1]中、60℃下浸渍8小时之后的粘接力(相对于铝箔),例如180°剥离粘合力(依据JIS Z0237,相对于铝箔,剥离温度:25℃,剥离速度:300mm/分钟:浸渍后粘接力)为0.5N/10mm以上[优选为1.0N/10mm以上(例如为1.0~2.5N/10mm)]。浸渍后的对铝箔的粘接力低于上述范围时,在锂离子电池内部使用时,在电解液中变得容易剥离,难以抑制电解液的劣化。
而且,本发明的电化学装置用粘合带在23℃下、在水中浸渍24小时之后的吸水率为0.2%以下(优选为0.15%以下,特别优选为0.10%以下)。吸水率高于上述范围时,难以防止由水分引起的电化学装置的缺陷。
对于本发明的电化学装置用粘合带,从保护粘合剂层表面、防粘连的观点等出发,可以在粘合剂层表面设置隔离膜(剥离衬垫)。隔离膜在将本发明的电化学装置用粘合带贴合在被粘物上时被剥离,并不一定要设置。对所使用的隔离膜没有限定,可以使用公知惯用的剥离纸等。例如可以使用用硅酮系、长链烷基系、氟系、硫化钼系等的剥离剂进行过表面处理的塑料薄膜、纸等具有剥离层的基材;由聚四氟乙烯、聚氯三氟乙烯、聚氟乙烯、聚偏二氟乙烯、四氟乙烯-六氟丙烯共聚物、氯氟乙烯-偏二氟乙烯共聚物等氟系聚合物形成的低粘接性基材;由烯烃系树脂(例如聚乙烯、聚丙烯等)等无极性聚合物形成的低粘接性基材等。
在本发明的电化学装置用粘合带为双面粘合带时,上述隔离膜可以设置在本发明的电化学装置用粘合带的两侧的粘合剂层表面,也可以在一侧的粘合面设置具有背面剥离层的隔离膜、通过将薄片卷绕使得隔离膜的背面剥离层与相反侧的粘合剂层表面接触。
本发明的电化学装置用粘合带例如适合用于制造锂离子电池等封入有非水系电解液的二次电池。
对前述非水系电解液没有特别限定,例如可列举出溶解有碳酸亚丙酯(PC)、碳酸亚乙酯(EC)等环状碳酸酯与碳酸二甲酯(DMC)、碳酸甲乙酯(EMC)、碳酸二乙酯(DEC)等链状碳酸酯的混合溶剂、以及作为电解质的LiPF6等锂盐的电解液等。
锂离子电池等非水系电解液二次电池具有将下述材料封入外装罐而成的结构:在正极芯体上涂布正极活性物质而成的正极板和在负极芯体上涂布负极活性物质而成的负极板隔着隔离膜层叠而得到的层叠型电极组,或者将在正极芯体上涂布正极活性物质而成的正极板与在负极芯体上涂布负极活性物质而成的负极板隔着隔离膜对置并卷绕成螺旋状而得到的卷绕型电极组,和从正极板、负极板引出的电极端子,以及电解液。
本发明的电化学装置用粘合带例如在上述锂离子电池等非水系电解液二次电池的制造中,可以为了防止由异物、毛边引起的隔离膜被贯穿、为了防止活性物质剥脱、为了改善将电极装入电池壳体内的适应性(例如固定由正极板/隔离膜/负极板构成的层叠体或固定前述层叠体的卷绕体)等而贴附在电池构成部件上使用。作为电池构成部件上的贴附部位,只要能够达前述目的的部位,则没有特别限定,例如可列举出极板、电极端子、极板端部、隔离膜的与极板端部接触的部分、活性物质的涂布部与未涂布部的边界部分、卷绕型电极组的卷尾部等(参照图3)。
实施例
以下,通过实施例来更具体地说明本发明,但本发明并不受这些实施例的限定。
实施例1
配合97重量份丙烯酸异壬酯、3重量份丙烯酸、0.1重量份作为引发剂的2,2’-偶氮二异丁腈(AIBN)、100重量份作为溶剂的醋酸乙酯,进行2小时的N2置换。在N2置换下,在60℃下进行6小时的聚合,得到重均分子量50万的丙烯酸系聚合物(1)。
在所得丙烯酸系聚合物(1)中以相对于其固体成分为5重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(1)。
将所得丙烯酸系粘合剂(1)涂布在作为基材的聚丙烯薄膜(商品名“TORAYFAN BO#2548”,Toray Industries,Inc.制造,厚度:20μm)上,使得干燥后的厚度为5μm,进行干燥,得到粘合带(1)。
实施例2
配合98重量份丙烯酸异辛酯、2重量份丙烯酸羟乙酯、0.1重量份AIBN、100重量份作为溶剂的甲苯,进行2小时的N2置换。在N2置换下,在60℃下进行6小时的聚合,得到重均分子量50万的丙烯酸系聚合物(2)。
在所得丙烯酸系聚合物(2)中以相对于其固体成分为4重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(2)。
将所得丙烯酸系粘合剂(2)涂布在作为基材的聚丙烯薄膜(商品名“TORAYFAN BO#2548”,Toray Industries,Inc.制造,厚度:20μm)上,使得干燥后的厚度为10μm,进行干燥,得到粘合带(2)。
实施例3
配合95重量份丙烯酸2-乙基己酯、5重量份丙烯酸、0.1重量份AIBN、100重量份醋酸乙酯,进行2小时的N2置换。在N2置换下,在60℃下进行6小时的聚合,得到重均分子量80万的丙烯酸系聚合物(3)。
在所得丙烯酸系聚合物(3)中以相对于其固体成分为3重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(3)。
将所得丙烯酸系粘合剂(3)涂布在作为基材的聚丙烯薄膜(商品名“TORAYFAN BO#2548”,Toray Industries,Inc.制造,厚度:30μm)上,使得干燥后的厚度为5μm,进行干燥,得到粘合带(3)。
比较例1
配合90重量份丙烯酸丁酯、10重量份丙烯酸、0.1重量份AIBN、100重量份醋酸乙酯,进行2小时的N2置换。此后,在60℃下进行6小时的聚合,得到重均分子量120万的丙烯酸系聚合物(4)。
在所得丙烯酸系聚合物(4)中以相对于其固体成分为2重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(4)。
将所得丙烯酸系粘合剂(4)涂布在作为基材的聚对苯二甲酸乙二醇酯薄膜(商品名“LUMIRROR S10”,Toray Industries,Inc.制造,厚度:25μm)上,使得干燥后的厚度为20μm,进行干燥,得到粘合带(4)。
比较例2
配合98重量份丙烯酸丁酯、20重量份N-丙烯酰基吗啉、2重量份丙烯酸、0.1重量份AIBN、100重量份醋酸乙酯,进行2小时的N2置换。此后,在60℃下进行6小时的聚合,得到重均分子量120万的丙烯酸系聚合物(5)。
在所得丙烯酸系聚合物(5)中以相对于其固体成分为2重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(5)。
将所得丙烯酸系粘合剂(5)涂布在作为基材的聚丙烯薄膜(商品名“TORAYFAN BO#2548”,Toray Industries,Inc.制造,厚度:30μm)上,使得干燥后的厚度为15μm,进行干燥,得到粘合带(5)。
比较例3
配合97重量份丙烯酸丁酯、3重量份丙烯酸、0.1重量份AIBN、100重量份甲苯,进行2小时的N2置换。在N2置换下,在60℃下进行6小时的聚合,得到重均分子量50万的丙烯酸系聚合物(6)。
在所得丙烯酸系聚合物(6)中以相对于其固体成分为0.5重量份的比例配合三官能性异氰酸酯系化合物(商品名“CORONATE L”,日本聚氨酯(株)制造),得到丙烯酸系粘合剂(6)。
将所得丙烯酸系粘合剂(6)涂布于作为基材的聚丙烯薄膜(商品名“TORAYFAN BO#2548”,Toray Industries,Inc.制造,厚度:30μm)上,使得干燥后的厚度为30μm,进行干燥,得到粘合带(6)。
对于实施例和比较例中得到的丙烯酸系粘合剂和粘合带,通过下述方法评价吸水率、凝胶率和防“粘合剂渗出”性。
吸水率的测定
对于实施例和比较例中得到的粘合带,依据JIS K7209,测定在23℃下、在水中浸渍24小时之后的吸水率(%)。
凝胶率的测定
在用剥离剂表面处理过的聚对苯二甲酸乙二醇酯薄膜(厚度:38μm)上涂布实施例和比较例中得到的丙烯酸系粘合剂,通过在130℃下干燥1分钟来除去溶剂,形成粘合剂层(厚度:25μm)。
以用剥离剂表面处理过的剥离薄膜覆盖所得粘合剂层,在50℃下熟化4天,得到凝胶率测定用粘合剂层。
取约0.1g所得凝胶率测定用粘合剂,用平均孔径0.2μm的多孔四氟乙烯薄片(商品名“NTF1122”,日东电工(株)制造)包裹,然后用风筝线捆住,测定此时的重量,以该重量为浸渍前重量。其中,该浸渍前重量是凝胶率测定用粘合剂、四氟乙烯薄片和风筝线的总重量。另外,还预先测定四氟乙烯薄片与风筝线的合计重量,以该重量为包装袋重量。
接着,将上述凝胶率测定用粘合剂用四氟乙烯薄片包裹、用风筝线捆住的材料(称为“样品”)投入装满醋酸乙酯的50ml容器,在23℃下静置7天。此后,从容器中取出样品(醋酸乙酯处理后),移到铝制杯子中,在130℃下在干燥机中干燥2小时来除去醋酸乙酯,然后测定重量,以该重量为浸渍后重量。接着,由下述式(1)算出凝胶率。
凝胶率(重量%)=(A-B)/(C-B)×100(1)
(式(1)中,A为浸渍后重量,B为包装袋重量,C为浸渍前重量。)
防粘合剂渗出性的评价
对于实施例和比较例中得到的粘合带,在其的粘合剂层面上贴合用剥离剂表面处理过的聚对苯二甲酸乙二醇酯薄膜(厚度:38μm),切割成10mm ×150mm宽度,制作样品。
将所得样品在23℃下放置24小时,此后,以与样品的基材面接触的方式配置在不锈钢板上,以2kg的辊往复一次来按压,然后使前述不锈钢板垂直竖立,观察各样品的1小时后的状况,基于下述基准进行评价。
评价基准
○:落下
×:未落下,保持在不锈钢板上
上述结果总结示于下表。
表1
Claims (3)
1.一种电化学装置用粘合带,其在塑料系基材的至少一面具有由丙烯酸系粘合剂形成的粘合剂层,其具有凝胶率为60%以上、厚度为1~15μm的粘合剂层,且在23℃下、在水中浸渍24小时之后的吸水率为0.2%以下,
所述丙烯酸系粘合剂含有如下的丙烯酸系聚合物:其是将至少包含含有碳数6~10的烷基的(甲基)丙烯酸烷基酯和含羧基单体的单体成分聚合而得到的,且所述单体成分的80重量%以上为所述含有碳数6~10的烷基的(甲基)丙烯酸烷基酯,所述单体成分的1~10重量%为含羧基单体,
所述丙烯酸系粘合剂含有相对于100重量份所述丙烯酸系聚合物为0.1~20重量份的交联剂。
2.根据权利要求1所述的电化学装置用粘合带,其中,含有碳数6~10的烷基的(甲基)丙烯酸烷基酯为选自(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸异辛酯和(甲基)丙烯酸异壬酯中的一种以上物质。
3.一种电化学装置,其具有权利要求1或2中的任一项所述的电化学装置用粘合带。
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JP2020017470A (ja) * | 2018-07-27 | 2020-01-30 | 株式会社クレハ | 基材フィルム、緩み防止用テープ、および蓄電デバイス |
KR20210090477A (ko) * | 2020-01-10 | 2021-07-20 | 에스케이이노베이션 주식회사 | 안정성이 향상된 배터리 모듈 |
CN113366690A (zh) * | 2021-03-31 | 2021-09-07 | 宁德新能源科技有限公司 | 一种电化学装置及电子装置 |
CN115838572B (zh) * | 2021-10-29 | 2024-03-26 | 宁德时代新能源科技股份有限公司 | 改性胶带的制造方法、二次电池、电池模块、电池包和用电装置 |
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JP3943217B2 (ja) | 1997-12-15 | 2007-07-11 | 日東電工株式会社 | 電池用接着剤又は粘着剤、及び粘着テープ又はシート |
JP4271756B2 (ja) | 1998-12-02 | 2009-06-03 | 日東電工株式会社 | 電池用接着剤又は粘着剤もしくは粘着テープ・シート |
JP2001074933A (ja) * | 1999-09-01 | 2001-03-23 | Nitto Denko Corp | 表面保護フィルム |
JP2002138261A (ja) * | 2000-11-06 | 2002-05-14 | Nitto Denko Corp | 粘着剤層付き光学フィルム |
JP4412895B2 (ja) * | 2002-12-05 | 2010-02-10 | 株式会社日本触媒 | 感圧接着剤組成物 |
JP4566527B2 (ja) * | 2003-08-08 | 2010-10-20 | 日東電工株式会社 | 再剥離型粘着シート |
JP2005179496A (ja) * | 2003-12-19 | 2005-07-07 | Nitto Denko Corp | 加熱剥離型粘着シート |
JP4562070B2 (ja) * | 2004-05-14 | 2010-10-13 | 日東電工株式会社 | 粘着剤組成物、粘着シート類、および表面保護フィルム |
TWI387629B (zh) * | 2004-07-26 | 2013-03-01 | Nitto Denko Corp | 壓感黏合劑組成物、壓感黏合片及表面保護膜 |
JP5085028B2 (ja) * | 2005-10-20 | 2012-11-28 | 日東電工株式会社 | 粘着型光学フィルムおよびその製造方法 |
JP4849993B2 (ja) * | 2006-08-14 | 2012-01-11 | 日東電工株式会社 | 粘着シート、その製造方法および積層セラミックシートの切断方法 |
JP5283838B2 (ja) * | 2006-11-04 | 2013-09-04 | 日東電工株式会社 | 熱剥離性粘着シート及び被着体回収方法 |
KR100922684B1 (ko) * | 2007-08-31 | 2009-10-19 | 제일모직주식회사 | 점착층용 광경화 조성물 및 이를 포함하는 다이싱 테이프 |
JP2010129699A (ja) * | 2008-11-26 | 2010-06-10 | Nitto Denko Corp | ダイシング・ダイボンドフィルム及び半導体装置の製造方法 |
JP5623020B2 (ja) * | 2009-02-27 | 2014-11-12 | 日東電工株式会社 | 粘着剤組成物、粘着剤層、及び、粘着シート |
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- 2011-08-03 CN CN201110221355.XA patent/CN102746800B/zh active Active
- 2011-09-15 CN CN2011203504079U patent/CN202246521U/zh not_active Expired - Lifetime
- 2011-10-06 US US13/267,247 patent/US20120270042A1/en not_active Abandoned
- 2011-10-06 US US13/267,255 patent/US20120270036A1/en not_active Abandoned
- 2011-10-24 EP EP11186278A patent/EP2514793A1/en not_active Withdrawn
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CN102746801A (zh) | 2012-10-24 |
KR101781645B1 (ko) | 2017-09-25 |
EP2514794A1 (en) | 2012-10-24 |
CN202246521U (zh) | 2012-05-30 |
US20120270042A1 (en) | 2012-10-25 |
US20120270036A1 (en) | 2012-10-25 |
EP2514793A1 (en) | 2012-10-24 |
CN102746800A (zh) | 2012-10-24 |
CN102746800B (zh) | 2016-05-04 |
KR20120119956A (ko) | 2012-11-01 |
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