JP2017036368A - Photosetting adhesive composition - Google Patents
Photosetting adhesive composition Download PDFInfo
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- JP2017036368A JP2017036368A JP2015156993A JP2015156993A JP2017036368A JP 2017036368 A JP2017036368 A JP 2017036368A JP 2015156993 A JP2015156993 A JP 2015156993A JP 2015156993 A JP2015156993 A JP 2015156993A JP 2017036368 A JP2017036368 A JP 2017036368A
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- Prior art keywords
- sensitive adhesive
- pressure
- acrylate
- adhesive composition
- photocurable
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- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000000853 adhesive Substances 0.000 title claims abstract description 18
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920001971 elastomer Polymers 0.000 claims abstract description 13
- 239000000806 elastomer Substances 0.000 claims abstract description 13
- 229920000428 triblock copolymer Polymers 0.000 claims abstract description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 7
- 229920006223 adhesive resin Polymers 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000004840 adhesive resin Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000010409 thin film Substances 0.000 abstract description 7
- 238000012545 processing Methods 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 3
- 238000011109 contamination Methods 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 14
- 239000004926 polymethyl methacrylate Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 9
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 8
- 150000003505 terpenes Chemical class 0.000 description 8
- 235000007586 terpenes Nutrition 0.000 description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- -1 alkali metal salt Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000002390 adhesive tape Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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
- 238000009472 formulation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HBKBEZURJSNABK-MWJPAGEPSA-N 2,3-dihydroxypropyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)OCC(O)CO HBKBEZURJSNABK-MWJPAGEPSA-N 0.000 description 1
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- KVPYIEPKUGXISR-UHFFFAOYSA-N 2-phenoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCC(C)OC1=CC=CC=C1 KVPYIEPKUGXISR-UHFFFAOYSA-N 0.000 description 1
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 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 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006146 polyetheresteramide block copolymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明はラベルやシートに薄膜で塗布する粘着剤で、被着体に一旦貼り付けた後に剥離を行う際に、特別な加工作業なしでも粘着剤残り等の汚染が生じにくい、再剥離性に優れた光硬化性粘着剤、およびそれを塗布した再剥離可能なラベルに関するものである。 The present invention is a pressure-sensitive adhesive that is applied to a label or sheet in a thin film, and when it is peeled off after being once attached to an adherend, it is difficult to cause contamination such as a pressure-sensitive adhesive residue even without a special processing operation. The present invention relates to an excellent photocurable pressure-sensitive adhesive and a removable label coated with the same.
近年、市場に出回る多くの商品には、価格、商標および内容物等の情報を表示したり、また当該商品を包装および結束するため、各種の粘着性テープ、粘着シートおよび粘着ラベル（以下「粘着ラベル類」という）が大量に使用されている。これらに使用する粘着剤は、環境問題の高まりから有機溶剤を使用しない組成物への移行が進んでおり、例えばアクリル系重合体とイソシアネート基を含有する（メタ）アクリル酸エステルと光重合開始剤による活性エネルギー線硬化型ホットメルト粘着剤が提案されている（特許文献１）。 In recent years, many products on the market have various adhesive tapes, adhesive sheets, and adhesive labels (hereinafter referred to as “adhesive”) for displaying information such as prices, trademarks and contents, and for packaging and binding the products. Labels) are used in large quantities. Adhesives used for these have been increasingly transferred to compositions that do not use organic solvents due to increased environmental problems. For example, (meth) acrylic acid esters containing an acrylic polymer and an isocyanate group and a photopolymerization initiator An active energy ray-curable hot melt pressure-sensitive adhesive is proposed (Patent Document 1).
更に最近では一旦貼り付けた後に剥離を行う場合、被着体に粘着剤が残りにくい再剥離性に優れる粘着ラベル類へのニーズが高まっており、こうした要求に対し、例えば半導体製造工程において剥離を行う際に紫外線を照射する粘着テープ（特許文献２）や、郵便物等で情報の機密性を保持する用途に用いられ、貼合わせ時に加圧を行う接着剤（特許文献３）等があるが、貼合わせおよび剥離時に特別な加工工程が必要という課題があった。またこうした特別な加工工程が必要とされない場合は、アクリル系モノマーとポリエーテルポリオールとアルカリ金属塩とからなる粘着剤層を有する粘着テープ（特許文献４）のように、モノマーからの重合反応が必要で製造プロセスが高価な配合となるため、特別な加工工程が不要で一般的な粘着ラベル類に使用できる、安価な無溶剤型粘着剤が求められていた。 More recently, there is a growing need for pressure-sensitive adhesive labels that have excellent removability, so that the adhesive does not remain on the adherend. There are adhesive tapes (Patent Document 2) that irradiate ultraviolet rays when performing, and adhesives (Patent Document 3) that are used for the purpose of maintaining the confidentiality of information with postal items, etc. There is a problem that a special processing step is required at the time of bonding and peeling. When such a special processing step is not required, a polymerization reaction from the monomer is required like an adhesive tape having an adhesive layer made of an acrylic monomer, a polyether polyol and an alkali metal salt (Patent Document 4). Therefore, an inexpensive solventless pressure-sensitive adhesive that can be used for general pressure-sensitive adhesive labels without requiring a special processing step has been demanded.
本発明の課題は、ラベルやシートに薄膜で塗布する粘着剤で、被着体に一旦貼り付けた後に剥離を行う際に粘着剤残り等の汚染が生じにくい、また貼合わせおよび剥離時に特別な加工工程が不要である安価な無溶剤型の光硬化性粘着剤、およびそれを塗布した再剥離可能なラベルを提供する事にある。 The subject of the present invention is a pressure-sensitive adhesive that is applied to a label or sheet as a thin film, and it is difficult to cause contamination such as a pressure-sensitive adhesive residue when it is peeled off after being once attached to an adherend. It is an object to provide an inexpensive solventless photocurable pressure-sensitive adhesive that does not require a processing step, and a removable label coated with the same.
請求項１の発明は、メチルメタアクリレート（以下「ＭＭＡ」という。）とブチルアクリレート（以下「ＢＡ」という。）のトリブロック共重合体エラストマー（Ａ）と、酸素または窒素原子を含む置換基を有する単官能（メタ）アクリレートモノマー（Ｂ）と、光重合開始剤（Ｃ）と、を含む光重合性粘着剤組成物であって、（Ａ）成分の含有量が全組成物１００重量部に対し１０〜３５重量部である光硬化性粘着剤組成物を提供する。 The invention of claim 1 includes a triblock copolymer elastomer (A) of methyl methacrylate (hereinafter referred to as “MMA”) and butyl acrylate (hereinafter referred to as “BA”), and a substituent containing an oxygen or nitrogen atom. A photopolymerizable pressure-sensitive adhesive composition comprising a monofunctional (meth) acrylate monomer (B) and a photopolymerization initiator (C), wherein the content of the component (A) is 100 parts by weight of the total composition The photocurable pressure-sensitive adhesive composition is provided in an amount of 10 to 35 parts by weight.
また請求項２の発明は、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）の硬さが、ＩＳＯ７６１９−１に準拠したタイプＡデュロメータで３０〜７０である、請求項１の光硬化性粘着剤組成物を提供する。 The invention according to claim 2 is the photocurable pressure-sensitive adhesive according to claim 1, wherein the hardness of the triblock copolymer elastomer (A) of MMA and BA is 30 to 70 in a type A durometer based on ISO7619-1. An agent composition is provided.
また請求項３の発明は、酸素または窒素原子を含む置換基を有する単官能アクリレートモノマー（Ｂ）が、ヒドロキシル基またはアミド基またはフェノキシ基を含有する、請求項１の光硬化性粘着剤組成物を提供する。 The invention according to claim 3 is the photocurable pressure-sensitive adhesive composition according to claim 1, wherein the monofunctional acrylate monomer (B) having a substituent containing an oxygen or nitrogen atom contains a hydroxyl group, an amide group or a phenoxy group. I will provide a.
また請求項４の発明は、組成物が３０００ｍＰａ・ｓ以下の粘度である請求項１〜３の光硬化性粘着剤組成物を提供する。 Moreover, invention of Claim 4 provides the photocurable adhesive composition of Claims 1-3 whose composition is a viscosity of 3000 mPa * s or less.
また請求項５の発明は、請求項１〜４のいずれかに記載の光硬化性粘着樹脂を塗布した再剥離可能なラベルを提供する。 Moreover, invention of Claim 5 provides the releasable label which apply | coated the photocurable adhesive resin in any one of Claims 1-4.
本発明の光硬化性薄膜粘着剤は、ラベルやシートに薄膜で塗布する粘着剤で、被着体に一旦貼り付けた後に剥離を行う際、特別な処理工程が無くとも粘着剤残り等の汚染が生じにくい再剥離性に優れた、また低コストの粘着剤として有用である。 The photocurable thin film pressure-sensitive adhesive of the present invention is a pressure-sensitive adhesive which is applied to a label or sheet as a thin film. It is useful as a low-cost pressure-sensitive adhesive that has excellent removability and is less likely to cause erosion.
本発明の組成物の構成は、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）と、酸素または窒素原子を含む置換基を有する単官能（メタ）アクリレートモノマー（Ｂ）と、光重合開始剤（Ｃ）である。なお、本明細書において、（メタ）アクリレートは、アクリレートとメタクリレートとの双方を包含する。 The composition of the present invention comprises a MMA and BA triblock copolymer elastomer (A), a monofunctional (meth) acrylate monomer (B) having a substituent containing oxygen or nitrogen atoms, and a photopolymerization initiator. (C). In the present specification, (meth) acrylate includes both acrylate and methacrylate.
本発明に使用されるＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）は、粘着剤層に柔軟性ともに適度な硬度を付与するベース樹脂であり、硬いポリマーであるポリメチルメタアクリレート（以下「ＰＭＭＡ」という。）で比較的柔らかいポリマーであるポリブチルアクリレート（以下「ＰＢＡ」という。）を挟んだ構造のトリブロック共重合体が好ましい。ＰＭＭＡとＰＢＡの重合比率は、硬さがタイプＡデュロメータで３０〜７０となる比率が好適である。 The MMA and BA triblock copolymer elastomer (A) used in the present invention is a base resin that imparts appropriate hardness to the pressure-sensitive adhesive layer, and is a hard polymer such as polymethyl methacrylate (hereinafter “ A triblock copolymer having a structure in which polybutyl acrylate (hereinafter referred to as “PBA”), which is a relatively soft polymer, is sandwiched between the PMMA and the PMMA is preferable. The polymerization ratio of PMMA and PBA is preferably such that the hardness is 30 to 70 with a type A durometer.
市販品としてはクラリティＬＡ２１４０Ｅ（クラレ製、ＰＭＭＡ／ＰｎＢＡ／ＰＭＭＡトリブロックポリマー、タイプＡ硬度３２）等がある。ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）の組成物全体１００重量部に対する配合量は１０〜３５重量部で、より好ましくは１５〜３０重量部である。１０重量部未満では凝集力不足により硬化皮膜ができず、３５重量部超では粘度が高くなり薄膜塗布ができなくなる。 Commercially available products include Clarity LA2140E (manufactured by Kuraray, PMMA / PnBA / PMMA triblock polymer, type A hardness 32). The blending amount of the MMA and BA triblock copolymer elastomer (A) with respect to 100 parts by weight of the total composition is 10 to 35 parts by weight, more preferably 15 to 30 parts by weight. If it is less than 10 parts by weight, a cured film cannot be formed due to insufficient cohesive force, and if it exceeds 35 parts by weight, the viscosity becomes so high that thin film coating cannot be performed.
本発明に使用される酸素または窒素原子を含む置換基を有する単官能（メタ）アクリレートモノマー（Ｂ）は、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）を溶解する反応性の溶媒であると同時に粘着剤の粘度を調整し、また粘着層に硬度を付与する役割を担う。そのため（Ｂ）は（Ａ）の良溶媒でなおかつ低粘度が好ましく、ヒドロキシル基またはアミド基またはフェノキシ基等の極性基を含有するアクリレートモノマーが好適である。 The monofunctional (meth) acrylate monomer (B) having a substituent containing an oxygen or nitrogen atom used in the present invention is a reactive solvent that dissolves the triblock copolymer elastomer (A) of MMA and BA. At the same time, it plays the role of adjusting the viscosity of the pressure-sensitive adhesive and imparting hardness to the pressure-sensitive adhesive layer. Therefore, (B) is a good solvent of (A) and preferably has a low viscosity, and an acrylate monomer containing a polar group such as a hydroxyl group, an amide group or a phenoxy group is preferred.
具体的にはヒドロキシル基を有するモノマーとして、ヒドロキシエチル（メタ）アクリレート、２‐ヒドロキシプロピル（メタ）アクリレート、３−ヒドロキシプロピル（メタ）アクリレート、２‐ヒドロキシブチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート等があり、またアミド基を有するモノマーとしては、アクリルアミド、Ｎ，Ｎ‐ジメチルアクリルアミド、Ｎ，Ｎ‐ジエチルアクリルアミド、Ｎ−イソプロピルアクリルアミド、アクリルロイルモルホリン等があり、更にフェノキシ基を有するモノマーとして、フェノキシエチルアクリレート、２-ヒドロキシ−３−フェノキシプロピルアクリレート、メチルフェノキシエチルアクリレート、フェノキシジエチレングリコールアクリレート、フェノキシポリエチレングリコールアクリレート等がある。これらを単独で用いてもよいし２種以上を併用してもよい。 Specifically, as a monomer having a hydroxyl group, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl ( Examples of the monomer having an amide group include acrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide, N-isopropylacrylamide, acryloylmorpholine, and a monomer having a phenoxy group. Phenoxyethyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, methylphenoxyethyl acrylate, phenoxydiethylene glycol acrylate, phenoxypolyethylene Examples include tylene glycol acrylate. These may be used alone or in combination of two or more.
本発明に使用される光重合開始剤（Ｃ）は、紫外線や電子線などの照射でラジカルを生じ、そのラジカルが重合反応のきっかけとなるもので、汎用の光重合開始剤で良い。具体的には２−ヒロドキシ−１−｛４−［４−（２−ヒドロキシ−２−メチル−プロピオニル）−ベンジル］フェニル｝−２−メチル−プロパン−１−オン、１−ヒドロキシ−シクロヘキシル−フェニル−ケトン、ビス（２，４，６‐トリメチルベンゾイル）‐フェニルフォスフィンオキサイド、２-ヒドロキシ-２-メチル-１-フェニル-プロパン-１-オン、１-[４-(２-ヒドロキシエトキシ)-フェニル]-２-ヒドロキシ-２-メチル-１-プロパン-１-オン等があり、単独または２種以上を組み合わせて使用できる。ラジカル重合性成分に対して、１〜１０重量％配合することが好ましい。 The photopolymerization initiator (C) used in the present invention may be a general-purpose photopolymerization initiator because radicals are generated by irradiation with ultraviolet rays or electron beams, and the radicals trigger a polymerization reaction. Specifically, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methyl-propan-1-one, 1-hydroxy-cyclohexyl-phenyl -Ketone, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1- [4- (2-hydroxyethoxy)- Phenyl] -2-hydroxy-2-methyl-1-propan-1-one, etc., which can be used alone or in combination of two or more. It is preferable to mix 1 to 10% by weight with respect to the radically polymerizable component.
本発明の粘着剤組成物には、性能を損なわない範囲で、必要により粘着付与剤、可塑剤、酸化防止剤及び濡れ性調整剤等の各種添加剤が含まれていても良い。 The pressure-sensitive adhesive composition of the present invention may contain various additives such as a tackifier, a plasticizer, an antioxidant, and a wettability adjuster as necessary, as long as the performance is not impaired.
本発明に使用される粘着付与剤は、ガムロジン、トールロジン、ウッドロジン、不均斉化ロジン、重合ロジン、これらロジンのグリセリンエステルやペンタエリスリトールエステル、これらの水素添加物などのロジン系樹脂、テルペン樹脂、炭化水素変性テルペン樹脂、これらの水素添加物などのテルペン系樹脂、テルペンフェノール樹脂、テルペンフェノール樹脂の水素添加物などのテルペンフェノール系樹脂、脂肪族系石油樹脂、脂環族系石油樹脂、芳香族系石油樹脂、共重合系石油樹脂、ジシクロペンタジエン系石油樹脂、ピュアーモノマー系石油樹脂、これらの水素添加物などの石油系樹脂、スチレン系樹脂、クマロンインデン系樹脂、アルキルフェノール系樹脂、キシレン系樹脂等がある。 The tackifier used in the present invention is a rosin resin such as gum rosin, tall rosin, wood rosin, disproportionated rosin, polymerized rosin, glycerin ester or pentaerythritol ester of these rosins, hydrogenated products thereof, terpene resin, carbonization Hydrogen-modified terpene resins, terpene resins such as these hydrogenated products, terpene phenol resins, terpene phenol resins such as hydrogenated terpene phenol resins, aliphatic petroleum resins, alicyclic petroleum resins, aromatic Petroleum resin, copolymer petroleum resin, dicyclopentadiene petroleum resin, pure monomer petroleum resin, petroleum resins such as hydrogenated products, styrene resin, coumarone indene resin, alkylphenol resin, xylene resin Etc.
これらの中でも、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）との相溶性の点から、低軟化点のロジンエステル、テルペンフェノール、スチレン樹脂が好ましく、これらを単独で用いてもよいし、２種以上を併用してもよい。市販品としてはＫＥ−３１１（荒川化学工業製、水添ロジンエステル）、ＹＳポリスターＴ８０（ヤスハラケミカル製、テルペンフェノール樹脂）等がある。 Among these, rosin ester, terpene phenol, and styrene resin having a low softening point are preferable from the viewpoint of compatibility with the triblock copolymer elastomer (A) of MMA and BA, and these may be used alone, Two or more kinds may be used in combination. Commercially available products include KE-311 (manufactured by Arakawa Chemical Industries, hydrogenated rosin ester), YS Polystar T80 (manufactured by Yashara Chemical, terpene phenol resin), and the like.
更に本発明に使用される可塑剤としてフタル酸エステル、ポリウレタン等あるが、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）との相溶性の点から、メチルメタアクリレートとブチルアクリレートの液状共重合体が好適である。市販品としてはクラリティＬＡ１１１４（クラレ製、ＰＭＭＡ／ＰｎＢＡジブロックポリマー）等がある。 Further, the plasticizer used in the present invention includes phthalate ester, polyurethane, etc., but from the point of compatibility with MMA and BA triblock copolymer elastomer (A), liquid copolymer of methyl methacrylate and butyl acrylate. Coalescence is preferred. Commercially available products include Clarity LA1114 (manufactured by Kuraray, PMMA / PnBA diblock polymer).
本発明の光硬化性粘着樹脂の粘度は３０００ｍＰａ・ｓ以下であり、更には５００〜２０００ｍＰａ・ｓが好ましい。３０００ｍＰａ・ｓを超えると塗布量のコントロールが難しくなり、安定して１０μｍ以下の薄膜塗布が困難となる。 The viscosity of the photocurable pressure-sensitive adhesive resin of the present invention is 3000 mPa · s or less, more preferably 500 to 2000 mPa · s. If it exceeds 3000 mPa · s, it becomes difficult to control the coating amount, and it becomes difficult to stably apply a thin film of 10 μm or less.
本発明の光硬化性粘着樹脂を基材に塗布する場合は、リバースロールコーター、グラビアコーター、バーコーターなど公知の塗工方法でよく、高圧水銀ランプ、メタルハライドランプ、キセノンランプ、無電極放電ランプ等の光源から、紫外線のような活性エネルギー線を照射してモノマーを硬化させる。 When applying the photocurable adhesive resin of the present invention to a substrate, a known coating method such as a reverse roll coater, a gravure coater, a bar coater may be used, such as a high pressure mercury lamp, a metal halide lamp, a xenon lamp, an electrodeless discharge lamp, etc. The monomer is cured by irradiating active energy rays such as ultraviolet rays from the light source.
光硬化性粘着樹脂を塗布する基材としては、紙類（例えばアート紙、つや紙、マシンコート紙等）、各種合成紙などのシート、フィルム類などで、従来からラベル類に使用されているものと同じものが利用できる。 As a base material to which the photo-curing adhesive resin is applied, papers (eg, art paper, glossy paper, machine-coated paper, etc.), sheets of various synthetic papers, films, etc. have been conventionally used for labels. The same thing can be used.
以下、本発明について実施例及び比較例を挙げてより詳細に説明するが、具体例を示すものであって、特にこれらに限定するものではない。なお表記が無い場合は、室温は２５℃相対湿度６５％の条件下で測定を行った。 EXAMPLES Hereinafter, although an Example and a comparative example are given and demonstrated in detail about this invention, a specific example is shown and it does not specifically limit to these. In addition, when there is no description, it measured on the conditions of 25 degreeC relative humidity 65% of room temperature.
実施例１
ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）としてクラリティＬＡ２１４０Ｅ（クラレ製、ＰＭＭＡ／ＰｎＢＡ／ＰＭＭＡトリブロックポリマー、タイプＡ硬度３２）を、酸素または窒素原子を含む置換基を有する単官能アクリレートモノマー（Ｂ）として４−ＨＢＡ（大阪有機化学工業製、４−ヒドロキシブチルアクリレート）を、光重合開始剤（Ｃ）としてＩｒｇａｃｕｒｅ１２７（ＢＡＳＦ製）を用い、均一に溶解するまで撹拌し実施例１の粘着剤組成物を調整した。
Example 1
Clarity LA2140E (manufactured by Kuraray, PMMA / PnBA / PMMA triblock polymer, type A hardness 32) as triblock copolymer elastomer (A) of MMA and BA, monofunctional acrylate monomer having a substituent containing oxygen or nitrogen atom (B) 4-HBA (manufactured by Osaka Organic Chemical Industry Co., Ltd., 4-hydroxybutyl acrylate) and Irgacure 127 (manufactured by BASF) as the photopolymerization initiator (C) were stirred until they were uniformly dissolved. The agent composition was prepared.
実施例２〜９
実施例１で用いた材料の他、ＭＭＡとＢＡのトリブロック共重合体エラストマー（Ａ）としてクラリティＬＡ２２５０（クラレ製、ＰＭＭＡ／ＰｎＢＡ／ＰＭＭＡトリブロックポリマー、タイプＡ硬度６５）およびＬＡ２３３０（クラレ製、ＰＭＭＡ／ＰｎＢＡ／ＰＭＭＡトリブロックポリマー、タイプＡ硬度３２）を、酸素または窒素原子を含む置換基を有する単官能アクリレートモノマー（Ｂ）としてＨＯＰ-Ａ（共栄社化学製、２−ヒドロキシプロピルアクリレート）およびＰＯ−Ａ（共栄社化学製、フェノキシエチルアクリレート）およびＤＥＡＡ（ＫＪケミカルズ製、ジエチルアクリルアミド）を、粘着付与剤としてＫＥ−３１１（荒川化学工業製、水添ロジンエステル）を、可塑剤としてＬＡ１１１４（クラレ製、ＰＭＭＡ／ＰｎＢＡジブロックポリマー）を用いて表１記載の配合にて、実施例２〜９の各粘着剤組成物を調製した。
Examples 2-9
In addition to the materials used in Example 1, as a triblock copolymer elastomer (A) of MMA and BA, Clarity LA2250 (manufactured by Kuraray, PMMA / PnBA / PMMA triblock polymer, type A hardness 65) and LA2330 (manufactured by Kuraray, PMMA / PnBA / PMMA triblock polymer, type A hardness 32) is used as a monofunctional acrylate monomer (B) having a substituent containing an oxygen or nitrogen atom as HOP-A (manufactured by Kyoeisha Chemical Co., Ltd., 2-hydroxypropyl acrylate) and PO. -A (manufactured by Kyoeisha Chemical Co., phenoxyethyl acrylate) and DEAA (manufactured by KJ Chemicals, diethyl acrylamide) as a tackifier, KE-311 (manufactured by Arakawa Chemical Industries, hydrogenated rosin ester), and LA1114 (manufactured by Kuraray) as a plasticizer , PMMA / Pn Each pressure-sensitive adhesive composition of Examples 2 to 9 was prepared with the formulation shown in Table 1 using (BA diblock polymer).
比較例１〜９
実施例１〜９で用いた材料の他、熱可塑性エラストマーとしてＴＰＡＥ１２（Ｔ＆ＫＴＯＫＡ製、ポリエーテルエステルアミドブロックポリマー）およびＲＸ７１−２５（亜細亜工業製、水添ポリブタジエン系ウレタンアクリレート）およびＲＸ８−３９（亜細亜工業製、ポリプロピレングリコール系ウレタンアクリレート）を、脂肪族アルキル系アクリレートモノマーとしてＮＯＡＡ（大阪有機化学工業製、ノルマルオクチルアクリレート）を、２官能アクリレートモノマーとして４ＥＧ−Ａ（共栄社化学製、ＰＥＧ２００ジアクリレート）を、可塑剤としてＧＩ−１０００（日本曹達製、末端水酸基含有水添ポリブタジエン）を用いて表１記載の配合にて、比較例１〜９の各粘着剤組成物を調製した。
Comparative Examples 1-9
In addition to the materials used in Examples 1 to 9, TPAE12 (manufactured by T & KTOKA, polyether ester amide block polymer) and RX71-25 (manufactured by Asia, hydrogenated polybutadiene-based urethane acrylate) and RX8-39 (manufactured by Asia) are used as thermoplastic elastomers. Industrial, polypropylene glycol urethane acrylate), NOAA (manufactured by Osaka Organic Chemical Industry, normal octyl acrylate) as an aliphatic alkyl acrylate monomer, and 4EG-A (Kyoeisha Chemical, PEG 200 diacrylate) as a bifunctional acrylate monomer The pressure-sensitive adhesive compositions of Comparative Examples 1 to 9 were prepared using GI-1000 (manufactured by Nippon Soda Co., Ltd., terminal hydroxyl group-containing hydrogenated polybutadiene) as a plasticizer in the formulation shown in Table 1.
粘着シートの作製
実施例１〜９および比較例１〜９の各粘着剤組成物を、易接着ポリエチレンテレフタレート（以下「ＰＥＴ」という）フィルム（東洋紡績製、厚み５０μｍ、商品名Ａ４３００）上に乾燥後の厚さが５μｍとなるように均一に塗布し、フュージョンＵＶシステムズジャパン製の無電極ＵＶ照射装置Ｆ３００Ｓ／ＬＣ−６Ｂを用い、Ｈバルブで出力１３００ｍＷ/ｃｍ２、積算光量が１００ｍＪ／ｃｍ２となる様に紫外線照射硬化し、粘着シートを作製した。
Preparation of pressure-sensitive adhesive sheets The pressure-sensitive adhesive compositions of Examples 1 to 9 and Comparative Examples 1 to 9 were dried on an easy-adhesive polyethylene terephthalate (hereinafter referred to as “PET”) film (made by Toyobo, thickness 50 μm, trade name A4300). The film is uniformly applied so that the subsequent thickness is 5 μm, and an electrodeless UV irradiation apparatus F300S / LC-6B manufactured by Fusion UV Systems Japan is used, and the output is 1300 mW / cm 2 and the integrated light quantity is 100 mJ / cm 2 using an H bulb. In the same manner, UV-curing was performed to prepare an adhesive sheet.
表１
Table 1
評価方法は以下の通りとした。 The evaluation method was as follows.
粘度：東機産業製のコーンプレート型粘度計ＲＣ−５５０を用い、コーン角３°Ｒ１７．６５で２５±１℃、回転数１０ｒｐｍで測定し、３０００ｍＰａ・ｓ以下を○、超えるものを×とした。 Viscosity: Using a cone-plate viscometer RC-550 manufactured by Toki Sangyo Co., Ltd., measured at a cone angle of 3 ° R17.65 at 25 ± 1 ° C and a rotation speed of 10 rpm. did.
接着強度：ミネベア製の引っ張り試験機ＴＧＩ−１ｋＮを用い、ステンレス板とＰＥＴフィルムとの１８０°剥離強度を、クロスヘッドスピード３００ｍｍ／ｍｉｎ．で測定した。試験片は上記で作製した粘着シートを１００×２５ｍｍの大きさにカットし、厚さ１ｍｍのステンレス板（ＳＵＳ３０４）に貼り合わせ、その上から重さ２Ｋｇのローラーで一往復加圧した後１時間放置して用いた。 Adhesive strength: Using Minebea tensile tester TGI-1kN, the 180 ° peel strength between the stainless steel plate and the PET film was measured at a crosshead speed of 300 mm / min. Measured with For the test piece, the pressure-sensitive adhesive sheet prepared above was cut into a size of 100 × 25 mm, bonded to a stainless steel plate (SUS304) having a thickness of 1 mm, and then pressed once with a 2 kg weight roller for 1 hour. Used as it was.
再剥離性：上記接着強度測定後のステンレス板を用い、目視と指触により糊残りを確認し、糊残りが無いものを○、べたつきがあるものを×とした。 Removability: Using the stainless steel plate after the measurement of the adhesive strength, the adhesive residue was confirmed by visual observation and finger touch.
評価結果を表２に示す。
表２
The evaluation results are shown in Table 2.
Table 2
実施例の各粘着剤組成物は各評価結果いずれも良好であった。一方、比較例の各粘着剤組成物においては、粘度、接着強度および再剥離性のいずれかの評価で本願発明に適さないものであった。
Each of the pressure-sensitive adhesive compositions of the examples was satisfactory in each evaluation result. On the other hand, each pressure-sensitive adhesive composition of Comparative Example was not suitable for the present invention in any evaluation of viscosity, adhesive strength and removability.
Claims (5)
A re-peelable label to which the photocurable adhesive resin according to claim 1 is applied.
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| JP2018111796A (en) * | 2017-01-11 | 2018-07-19 | アイカ工業株式会社 | Led curable moisture proof insulation coating agent composition |
| JP2019065242A (en) * | 2017-10-05 | 2019-04-25 | リンテック株式会社 | Display label |
| EP3597680A1 (en) * | 2018-07-18 | 2020-01-22 | ThreeBond Co., Ltd. | Adhesive composition, cured product, and bonded body |
| JP2020147698A (en) * | 2019-03-14 | 2020-09-17 | セメダイン株式会社 | Photo-curable adhesive composition |
| JP2021038392A (en) * | 2015-09-29 | 2021-03-11 | 協立化学産業株式会社 | Compatibilized composition, adhesive composition, composite structure, and production method and disassembling method of composite structure |
| JP2021147541A (en) * | 2020-03-19 | 2021-09-27 | 三菱ケミカル株式会社 | Active energy ray-curable peelable adhesive composition and peelable adhesive sheet |
| WO2022009913A1 (en) * | 2020-07-07 | 2022-01-13 | 株式会社Moresco | Adhesive composition and use of same |
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| JP2013203977A (en) * | 2012-03-29 | 2013-10-07 | Dainippon Printing Co Ltd | Tacky sheet and non-tacky sheet |
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| JP2021038392A (en) * | 2015-09-29 | 2021-03-11 | 協立化学産業株式会社 | Compatibilized composition, adhesive composition, composite structure, and production method and disassembling method of composite structure |
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| US20200024493A1 (en) * | 2018-07-18 | 2020-01-23 | Threebond Co., Ltd. | Adhesive composition, cured product, and bonded body |
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| JP7376766B2 (en) | 2018-07-18 | 2023-11-09 | 株式会社スリーボンド | Adhesive compositions, cured products and bonded products |
| CN110734705B (en) * | 2018-07-18 | 2023-04-14 | 三键有限公司 | Adhesive composition, cured product, and bonded body |
| JP2020147698A (en) * | 2019-03-14 | 2020-09-17 | セメダイン株式会社 | Photo-curable adhesive composition |
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| JP2021147541A (en) * | 2020-03-19 | 2021-09-27 | 三菱ケミカル株式会社 | Active energy ray-curable peelable adhesive composition and peelable adhesive sheet |
| WO2022009913A1 (en) * | 2020-07-07 | 2022-01-13 | 株式会社Moresco | Adhesive composition and use of same |
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