JP2021084927A - Adhesive composition, adhesive and adhesive sheet - Google Patents
Adhesive composition, adhesive and adhesive sheet Download PDFInfo
- Publication number
- JP2021084927A JP2021084927A JP2019212773A JP2019212773A JP2021084927A JP 2021084927 A JP2021084927 A JP 2021084927A JP 2019212773 A JP2019212773 A JP 2019212773A JP 2019212773 A JP2019212773 A JP 2019212773A JP 2021084927 A JP2021084927 A JP 2021084927A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- pressure
- sensitive adhesive
- acrylate
- adhesive
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 230000001070 adhesive effect Effects 0.000 title abstract description 45
- 239000000853 adhesive Substances 0.000 title abstract description 44
- 239000011148 porous material Substances 0.000 claims abstract description 34
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 33
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920006223 adhesive resin Polymers 0.000 claims abstract description 21
- 230000009477 glass transition Effects 0.000 claims abstract description 18
- 239000002245 particle Substances 0.000 claims abstract description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 96
- 239000010410 layer Substances 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 9
- 239000004840 adhesive resin Substances 0.000 abstract description 13
- 239000000758 substrate Substances 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 74
- -1 and for example Substances 0.000 description 53
- 239000000178 monomer Substances 0.000 description 43
- 239000003431 cross linking reagent Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000007423 decrease Effects 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 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
- 239000011248 coating agent Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000003926 acrylamides Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000001877 deodorizing effect Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- 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 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 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 3
- 238000012546 transfer Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003522 acrylic cement Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000005202 decontamination Methods 0.000 description 2
- 230000003588 decontaminative effect Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000010903 husk Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
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- 229920001296 polysiloxane Polymers 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- VBZBISQOWJYWCC-UHFFFAOYSA-N 2-(2-carboxypropan-2-yldiazenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)N=NC(C)(C)C(O)=O VBZBISQOWJYWCC-UHFFFAOYSA-N 0.000 description 1
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical group O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
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- 239000006096 absorbing agent Substances 0.000 description 1
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- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 239000012159 carrier gas Substances 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
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- 239000000470 constituent Substances 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
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- 238000011067 equilibration Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
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- 239000003759 ester based solvent Substances 0.000 description 1
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- 238000005886 esterification reaction Methods 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
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- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- YVOQADGLLJCMOE-UHFFFAOYSA-N n-[6-(aziridine-1-carbonylamino)hexyl]aziridine-1-carboxamide Chemical compound C1CN1C(=O)NCCCCCCNC(=O)N1CC1 YVOQADGLLJCMOE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- TZYULTYGSBAILI-UHFFFAOYSA-M trimethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC=C TZYULTYGSBAILI-UHFFFAOYSA-M 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、粘着剤組成物に関し、更に詳しくは、適度な粘着力と貼り合せた部材（基材、被着体等）に含まれる低分子化合物由来の臭気を吸着する粘着剤組成物及びそれを用いた粘着剤、粘着シートに関するものである。 The present invention relates to a pressure-sensitive adhesive composition, and more specifically, a pressure-sensitive adhesive composition that adsorbs an odor derived from a low-molecular-weight compound contained in a member (base material, adherend, etc.) bonded with an appropriate adhesive strength and the pressure-sensitive adhesive composition. It relates to an adhesive and an adhesive sheet using.
従来より、粘着性を有する樹脂を加工した粘着剤が様々な用途で用いられている。かかる粘着剤は、各種の基材や部材表面に積層され粘着シートや粘着パッドとして用いられる。このような粘着シートとしては、部材の表面を保護するための表面保護用や、電子部品貼り合せ用、壁紙貼り合せ用、カーペット用、梱包用など様々な用途に展開されている。
このような粘着性を有する樹脂には、アクリル系樹脂やポリエステル系樹脂、ウレタン系樹脂、シリコーン系樹脂が主に使用されている。
Conventionally, adhesives processed from adhesive resins have been used for various purposes. Such an adhesive is laminated on various base materials and member surfaces and used as an adhesive sheet or an adhesive pad. Such adhesive sheets are used for various purposes such as surface protection for protecting the surface of a member, electronic component bonding, wallpaper bonding, carpeting, and packaging.
Acrylic resins, polyester resins, urethane resins, and silicone resins are mainly used as the resins having such adhesiveness.
また、空気中や溶液中の分子吸着剤として多孔質構造を有する物質（多孔質材料）が知られており、例えば、ゼオライトや多孔質シリカ、活性炭などがフィルターとして知られている。このような材料を不織布等に包みシート状にしたものが、溶剤用のマスクや脱臭フィルターとして用いられている。
また、上記の多孔質材料を基材とした粘着シートも提案されている（例えば、特許文献１参照）。
Further, a substance having a porous structure (porous material) is known as a molecular adsorbent in air or a solution, and for example, zeolite, porous silica, activated carbon and the like are known as filters. A sheet of such a material wrapped in a non-woven fabric or the like is used as a mask for a solvent or a deodorizing filter.
Further, an adhesive sheet using the above-mentioned porous material as a base material has also been proposed (see, for example, Patent Document 1).
しかしながら、従来のシート型脱臭剤は主に、空気中や溶液中の分子吸着を目的としており、固体表面に残留した臭気成分等を積極的に吸着できるものではなかった。
また、上記の多孔質材料を基材とした粘着シートは、被着体面と反対側に多孔質材料が存在することになり、被着体から臭気成分等を吸着することについては一切考慮されていないものであった。
However, the conventional sheet-type deodorant is mainly intended for molecular adsorption in air or solution, and cannot positively adsorb odorous components remaining on the solid surface.
Further, in the pressure-sensitive adhesive sheet using the above-mentioned porous material as a base material, the porous material exists on the side opposite to the adherend surface, and the adsorption of odorous components and the like from the adherend is completely considered. It wasn't.
そこで、本発明は、このような背景下において、適度な粘着力を有し、貼り合せた部材（基材、被着体等）に残留する分子を吸着し、臭気や有害性を低減できる粘着剤組成物、更に粘着剤及び粘着シートを提供することを目的とするものである。 Therefore, the present invention has an appropriate adhesive force against such a background, and can adsorb molecules remaining on the bonded members (base material, adherend, etc.) to reduce odor and harmfulness. It is an object of the present invention to provide an agent composition, and further an adhesive and an adhesive sheet.
しかるに、本発明者らはかかる事情に鑑み鋭意研究を重ねた結果、粘着性樹脂に多孔質材料を含有させた粘着剤組成物を用いて粘着シートとすることにより、粘着性が良好でありながら、空気中や溶液中の臭気成分ではなく、これまではあまり考慮されてこなかった部材（基材、被着体等）中の臭気成分や有害成分を効率よく吸着することができることを見出し、本発明を完成した。 However, as a result of intensive studies in view of such circumstances, the present inventors have made an adhesive sheet by using an adhesive composition containing a porous material in an adhesive resin, although the adhesiveness is good. , We found that it is possible to efficiently adsorb odorous components and harmful components in members (base materials, adherends, etc.) that have not been considered so far, instead of odorous components in air or solution. The invention was completed.
即ち、本発明の要旨は、ガラス転移温度が０℃以下の粘着性樹脂（Ａ）及び多孔質材料（Ｂ）を含有することを特徴とする粘着剤組成物に関するものである。
更に、本発明は、前記粘着剤組成物が架橋された粘着剤、かかる粘着剤からなる粘着剤層を有する粘着シートをも提供するものである。
That is, the gist of the present invention relates to a pressure-sensitive adhesive composition containing a pressure-sensitive adhesive resin (A) having a glass transition temperature of 0 ° C. or lower and a porous material (B).
Furthermore, the present invention also provides a pressure-sensitive adhesive in which the pressure-sensitive adhesive composition is crosslinked, and a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer composed of such pressure-sensitive adhesive.
通常溶剤や低分子成分を含む粘着性樹脂に、直接多孔質材料を添加しても、多孔質材料の細孔がかかる溶剤や低分子成分により詰まってしまい、臭気成分の吸着性能が失活してしまうと懸念されるところであるが、敢えて粘着性樹脂に多孔質材料を含有させたところ、予想に反して良好な粘着性能を有するとともに部材中の臭気成分や有害成分に対する吸着性能に優れた粘着剤を形成する粘着剤組成物が得られることを見出したのである。 Even if the porous material is directly added to the adhesive resin containing a normal solvent or low molecular weight component, the pores of the porous material are clogged by the solvent or low molecular weight component, and the adsorption performance of the odorous component is deactivated. However, when the adhesive resin contains a porous material, it has unexpectedly good adhesive performance and has excellent adsorption performance to odorous components and harmful components in the member. They have found that a pressure-sensitive adhesive composition that forms an agent can be obtained.
本発明の粘着剤組成物は、ガラス転移温度が０℃以下の粘着性樹脂（Ａ）及び多孔質材料（Ｂ）を含有する粘着剤組成物である。そのため、かかる粘着剤組成物を用いて得られる粘着剤は、良好な粘着性能を有するとともに部材中の臭気成分や有害成分に対する吸着性能に優れたものとなる。
したがって、本発明の粘着剤組成物は、種々の用途、たとえば建材用途（壁紙用や養生用）、表面保護用途、汚染除去用途、車載部材用途、航空機用途などに好適に用いることができる。
The pressure-sensitive adhesive composition of the present invention is a pressure-sensitive adhesive composition containing a pressure-sensitive adhesive resin (A) having a glass transition temperature of 0 ° C. or lower and a porous material (B). Therefore, the pressure-sensitive adhesive obtained by using such a pressure-sensitive adhesive composition has good pressure-sensitive adhesive performance and excellent adsorption performance for odorous components and harmful components in the member.
Therefore, the pressure-sensitive adhesive composition of the present invention can be suitably used for various purposes such as building material applications (wallpaper and curing), surface protection applications, decontamination applications, in-vehicle member applications, aircraft applications, and the like.
本発明においては、貼り合せた部材表面に粘着剤層が接触するとともに、部材から粘着剤層に分子が拡散し、粘着剤層に含まれる多孔質材料に臭気成分や有害成分等の分子がトラップされることとなり、その結果、単に多孔質材料を部材近傍に置く以上に、より積極的に部材からの分子吸着が進行し、脱臭効果が発現するものと考えられる。 In the present invention, the pressure-sensitive adhesive layer comes into contact with the surface of the bonded member, molecules diffuse from the member to the pressure-sensitive adhesive layer, and molecules such as odorous components and harmful components are trapped in the porous material contained in the pressure-sensitive adhesive layer. As a result, it is considered that the molecular adsorption from the member proceeds more positively than simply placing the porous material in the vicinity of the member, and the deodorizing effect is exhibited.
以下に、本発明を詳細に説明する。
本発明の粘着剤組成物は、ガラス転移温度が０℃以下の粘着性樹脂（Ａ）及び多孔質材料（Ｂ）を含有するものである。
Hereinafter, the present invention will be described in detail.
The pressure-sensitive adhesive composition of the present invention contains a pressure-sensitive adhesive resin (A) having a glass transition temperature of 0 ° C. or lower and a porous material (B).
上記粘着性樹脂（Ａ）は、ガラス転移温度が０℃以下の樹脂であり、常温ではタックを有するものである。このような樹脂としては、例えば、アクリル系樹脂、ゴム系樹脂、ポリエステル系樹脂、ウレタン系樹脂、シリコーン系樹脂等があげられる。これらのなかでも、粘着物性に優れる点でアクリル系樹脂が好ましい。 The adhesive resin (A) is a resin having a glass transition temperature of 0 ° C. or lower and has a tack at room temperature. Examples of such resins include acrylic resins, rubber resins, polyester resins, urethane resins, silicone resins and the like. Among these, an acrylic resin is preferable because it has excellent adhesive physical properties.
以下、アクリル系樹脂について説明する。
なお、本発明において、「（メタ）アクリル」とはアクリルあるいはメタクリルを、「（メタ）アクリロイル」とはアクリロイルあるいはメタクリロイルを、「（メタ）アクリレート」とはアクリレートあるいはメタクリレートをそれぞれ意味するものである。
また、「アクリル系樹脂」とは、少なくとも１種の（メタ）アクリル系モノマーを含む重合成分を重合して得られる樹脂のことをいう。
Hereinafter, the acrylic resin will be described.
In the present invention, "(meth) acrylic" means acrylic or methacrylic, "(meth) acryloyl" means acryloyl or methacrylic, and "(meth) acrylate" means acrylate or methacrylate. ..
Further, the "acrylic resin" refers to a resin obtained by polymerizing a polymerization component containing at least one (meth) acrylic monomer.
本発明で用いるアクリル系樹脂は、（メタ）アクリル系モノマーを主成分とし、必要に応じて、他の各種の重合性モノマーを含有する重合成分を重合してなるアクリル系樹脂が挙げられる。
なお、「主成分とする」とは、重合成分全体に対して通常４０重量％以上、好ましくは５０重量％以上、更に好ましくは６０重量％以上含有することを意味する。
Examples of the acrylic resin used in the present invention include acrylic resins having a (meth) acrylic monomer as a main component and, if necessary, polymerizing a polymerization component containing various other polymerizable monomers.
The term "main component" means that the polymer is usually contained in an amount of 40% by weight or more, preferably 50% by weight or more, and more preferably 60% by weight or more based on the entire polymerization component.
上記（メタ）アクリル系モノマーとしては、（メタ）アクリル酸またはその誘導体、（メタ）アクリルアミドまたはその誘導体等が挙げられる。 Examples of the (meth) acrylic monomer include (meth) acrylic acid or a derivative thereof, (meth) acrylamide or a derivative thereof.
上記（メタ）アクリル酸の誘導体としては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、２−メチル−２−ニトロプロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｓ−ブチル（メタ）アクリレート、ｔ−ブチル（メタ）アクリレート、ｎ−ペンチル（メタ）アクリレート、ｔ−ペンチル（メタ）アクリレート、３−ペンチル（メタ）アクリレート、２，２−ジメチルブチル（メタ）アクリレート、ｎ−ヘキシル（メタ）アクリレート、セチル（メタ）アクリレート、ｎ−オクチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、４−メチル−２−プロピルペンチル（メタ）アクリレート、ｎ−オクタデシル（メタ）アクリレート等の（メタ）アクリル酸のアルキルエステル等が挙げられる。 Examples of the derivative of the (meth) acrylic acid include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, and 2-methyl-2-nitropropyl (meth). Acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, s-butyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, t-pentyl (meth) acrylate, 3- Pentyl (meth) acrylate, 2,2-dimethylbutyl (meth) acrylate, n-hexyl (meth) acrylate, cetyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 4-methyl Examples thereof include alkyl esters of (meth) acrylic acids such as -2-propylpentyl (meth) acrylate and n-octadecyl (meth) acrylate.
また、上記（メタ）アクリル酸の誘導体の他の例として、例えば、シクロヘキシル（メタ）アクリレート、シクロペンチル（メタ）アクリレート等のシクロアルキル（メタ）アクリレート；ベンジル（メタ）アクリレート等のアラルキル（メタ）アクリレート；ビフェニルオキシエチル（メタ）アクリレート等のビフェニルオキシ構造含有（メタ）アクリレート；２−イソボルニル（メタ）アクリレート、２−ノルボルニルメチル（メタ）アクリレート、５−ノルボルネン−２−イル−メチル（メタ）アクリレート、３−メチル−２−ノルボルニルメチル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレ−ト、ジシクロペンテニルオキシエチル（メタ）アクリレ−ト、ジシクロペンタニル（メタ）アクリレート等の多環式（メタ）アクリレート；２−メトキシエチル（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、２−メトキシメトキシエチル（メタ）アクリレート、３−メトキシブチル（メタ）アクリレート、メトキシジエチレングリコール（メタ）アクリレート、エトキシジエチレングリコール（メタ）アクリレート、メトキシポリエチレングリコール（メタ）アクリレート、エチルカルビトール（メタ）アクリレート、フェノキシエチル（メタ）アクリレート、アルキルフェノキシポリエチレングリコール（メタ）アクリレート等のアルコキシ基またはフェノキシ基含有（メタ）アクリレート；等が挙げられる。 Further, as another example of the above-mentioned (meth) acrylic acid derivative, for example, cycloalkyl (meth) acrylate such as cyclohexyl (meth) acrylate and cyclopentyl (meth) acrylate; aralkyl (meth) acrylate such as benzyl (meth) acrylate. Biphenyloxy structure-containing (meth) acrylates such as biphenyloxyethyl (meth) acrylates; 2-isobornyl (meth) acrylates, 2-norbornylmethyl (meth) acrylates, 5-norbornen-2-yl-methyl (meth) Acrylate, 3-methyl-2-norbornylmethyl (meth) acrylate, dicyclopentenyl (meth) acrylicate, dicyclopentenyloxyethyl (meth) acrylicate, dicyclopentanyl (meth) acrylate, etc. Cyclic (meth) acrylate; 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-methoxymethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate , Ethoxydiethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethylcarbitol (meth) acrylate, phenoxyethyl (meth) acrylate, alkylphenoxypolyethylene glycol (meth) acrylate and other alkoxy or phenoxy group-containing (meth) Acrylate; and the like.
更に、（メタ）アクリル酸の誘導体としては、官能基含有モノマーも挙げられ、例えば、２−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、６−ヒドロキシヘキシル（メタ）アクリレート、８−ヒドロキシオクチル（メタ）アクリレート、１０−ヒドロキシデシル（メタ）アクリレート、１２−ヒドロキシラウリル（メタ）アクリレート等のヒドロキシアルキル（メタ）アクリレートや、［４−（ヒドロキシメチル）シクロヘキシル］メチルアクリレート、シクロヘキサンジメタノールモノ（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート等の水酸基含有（メタ）アクリレート；グリシジル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレートグリシジルエーテル等のエポキシ基含有（メタ）アクリレート；２，２，２−トリフルオロエチル（メタ）アクリレート、２，２，２−トリフルオロエチルエチル（メタ）アクリレート、テトラフルオロプロピル（メタ）アクリレート、ヘキサフルオロプロピル（メタ）アクリレート、オクタフルオロペンチル（メタ）アクリレート、ヘプタデカフルオロデシル（メタ）アクリレート、３−クロロ−２−ヒドロキシプロピル（メタ）アクリレート等のハロゲン含有（メタ）アクリレート；ジメチルアミノエチル（メタ）アクリレート等のアルキルアミノアルキル（メタ）アクリレート；３−オキセタニルメチル（メタ）アクリレート、３−メチル−オキセタニルメチル（メタ）アクリレート、３−エチル−オキセタニルメチル（メタ）アクリレート、３−ブチル−オキセタニルメチル（メタ）アクリレート、３−ヘキシル−オキセタニルメチル（メタ）アクリレート等のオキセタン基含有（メタ）アクリレート；等が挙げられる。 Further, examples of the derivative of (meth) acrylic acid include functional group-containing monomers, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2 -Hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) ) Hydroxylalkyl (meth) acrylates such as acrylates and hydroxyl groups such as [4- (hydroxymethyl) cyclohexyl] methyl acrylates, cyclohexanedimethanol mono (meth) acrylates, and 2-hydroxy-3-phenoxypropyl (meth) acrylates ( Meta) Acrylate; Epoxy group-containing (meth) acrylate such as glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether; 2,2,2-trifluoroethyl (meth) acrylate, 2,2,2- Trifluoroethyl ethyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, hexafluoropropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, 3-chloro-2-hydroxypropyl Halogen-containing (meth) acrylates such as (meth) acrylates; alkylaminoalkyl (meth) acrylates such as dimethylaminoethyl (meth) acrylates; 3-oxetanylmethyl (meth) acrylates, 3-methyl-oxetanylmethyl (meth) acrylates, Examples thereof include oxetane group-containing (meth) acrylates such as 3-ethyl-oxetanylmethyl (meth) acrylate, 3-butyl-oxetanylmethyl (meth) acrylate, and 3-hexyl-oxetanylmethyl (meth) acrylate.
また、前記（メタ）アクリルアミドの誘導体としては、例えば、Ｎ−メチル（メタ）アクリルアミド、Ｎ，Ｎ−ジメチル（メタ）アクリルアミド、Ｎ，Ｎ−ジエチル（メタ）アクリルアミド、Ｎ−イソプロピル（メタ）アクリルアミド、Ｎ−ブチル（メタ）アクリルアミド、Ｎ−ヘキシル（メタ）アクリルアミド等のＮ−アルキル基含有（メタ）アクリルアミド誘導体；Ｎ−メチロール（メタ）アクリルアミド、Ｎ−ヒドロキシエチル（メタ）アクリルアミド、Ｎ−メチロール−Ｎ−プロパン（メタ）アクリルアミド等のＮ−ヒドロキシアルキル基含有（メタ）アクリルアミド誘導体；アミノメチル（メタ）アクリルアミド、アミノエチル（メタ）アクリルアミド等のＮ−アミノアルキル基含有（メタ）アクリルアミド誘導体；Ｎ−メトキシメチル（メタ）アクリルアミド、Ｎ−エトキシメチル（メタ）アクリルアミド等のＮ−アルコキシ基含有（メタ）アクリルアミド誘導体；メルカプトメチル（メタ）アクリルアミド、メルカプトエチル（メタ）アクリルアミド等のＮ−メルカプトアルキル基含有（メタ）アクリルアミド誘導体；Ｎ−アクリロイルモルホリン、Ｎ−アクリロイルピペリジン、Ｎ−メタクリロイルピペリジン、Ｎ−アクリロイルピロリジン等の複素環含有（メタ）アクリルアミド誘導体；等が挙げられる。 Examples of the (meth) acrylamide derivative include N-methyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, and N-isopropyl (meth) acrylamide. N-alkyl group-containing (meth) acrylamide derivatives such as N-butyl (meth) acrylamide and N-hexyl (meth) acrylamide; N-methylol (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-methylol-N N-Hydroxyalkyl group-containing (meth) acrylamide derivatives such as propane (meth) acrylamide; N-aminoalkyl group-containing (meth) acrylamide derivatives such as aminomethyl (meth) acrylamide and aminoethyl (meth) acrylamide; N-methoxy N-alkoxy group-containing (meth) acrylamide derivatives such as methyl (meth) acrylamide and N-ethoxymethyl (meth) acrylamide; N-mercaptoalkyl group-containing (meth) acrylamide such as mercaptomethyl (meth) acrylamide and mercaptoethyl (meth) acrylamide. ) Acrylamide; Examples thereof include heterocyclic (meth) acrylamide derivatives such as N-acrylamide morpholine, N-acrylloylpiperidin, N-methacryloylpiperidin, and N-acrylloylpyrrolidin.
また、本発明において、アクリル系樹脂（Ａ）に用いることのできる、（メタ）アクリル系モノマー以外の重合性モノマー（以下、「その他の重合性モノマー」という）としては、例えば、クロトン酸、マレイン酸、無水マレイン酸、フマル酸、シトラコン酸、グルタコン酸、イタコン酸、アクリルアミド−Ｎ−グリコール酸、ケイ皮酸等の不飽和カルボン酸；酢酸ビニル、プロピオン酸ビニル、ステアリン酸ビニル、安息香酸ビニル等のカルボン酸ビニルエステルモノマー；スチレン、α−メチルスチレン等の芳香環を含有するモノマー；アクリロニトリル、メタクリロニトリル、塩化ビニル、塩化ビニリデン、アルキルビニルエーテル、ビニルトルエン、ビニルピリジン、ビニルピロリドン、イタコン酸ジアルキルエステル、フマル酸ジアルキルエステル、アリルアルコール、アクリルクロライド、メチルビニルケトン、アリルトリメチルアンモニウムクロライド、ジメチルアリルビニルケトン等が挙げられる。これらは単独で用いてもよいし、２種以上を併用してもよい。 Further, in the present invention, examples of the polymerizable monomer other than the (meth) acrylic monomer (hereinafter referred to as “other polymerizable monomer”) that can be used for the acrylic resin (A) include crotonic acid and malein. Unsaturated carboxylic acids such as acids, maleic anhydride, fumaric acid, citraconic acid, glutaconic acid, itaconic acid, acrylamide-N-glycolic acid, silicic acid; vinyl acetate, vinyl propionate, vinyl stearate, vinyl benzoate, etc. Carboxylic acid vinyl ester monomer; Monomer containing aromatic rings such as styrene and α-methylstyrene; acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, alkyl vinyl ether, vinyl toluene, vinyl pyridine, vinyl pyrrolidone, dialkyl ester of itaconic acid. , Fumaric acid dialkyl ester, allyl alcohol, acrylic chloride, methyl vinyl ketone, allyl trimethyl ammonium chloride, dimethyl allyl vinyl ketone and the like. These may be used alone or in combination of two or more.
上記の（メタ）アクリル系モノマーは、単独で用いても２種以上を組み合わせて用いてもよい。そして、中でも、（メタ）アクリル酸のアルキルエステルであるモノマーが好適に用いられ、粘着物性の点で、特には炭素数１〜２０のアルキル（メタ）アクリレートが好ましく、更には炭素数が１〜１２のものが好ましく、殊には１〜８のものが好ましい。 The above (meth) acrylic monomer may be used alone or in combination of two or more. Among them, a monomer which is an alkyl ester of (meth) acrylic acid is preferably used, and in terms of adhesive characteristics, an alkyl (meth) acrylate having 1 to 20 carbon atoms is particularly preferable, and further, an alkyl (meth) acrylate having 1 to 20 carbon atoms is preferable. Twelve are preferable, and 1 to 8 are particularly preferable.
更に、本発明に用いられるアクリル系樹脂（Ａ）は、粘着剤とした際の凝集力を向上させる点で、重合成分として、官能基含有モノマーを含有することが好ましく、かかる官能基含有モノマーは、水酸基含有モノマー及びカルボキシ基含有モノマーから選ばれる少なくとも１種のモノマーを含む官能基含有モノマーであることが好ましい。中でも、（メタ）アクリロイル基を有する官能基含有モノマーが好ましい。これらの中でも、水酸基含有モノマー及びカルボキシ基含有モノマーが粘着物性と樹脂溶液の保存安定性のバランスに優れる点で好ましい。 Further, the acrylic resin (A) used in the present invention preferably contains a functional group-containing monomer as a polymerization component in terms of improving the cohesive force when used as a pressure-sensitive adhesive, and the functional group-containing monomer is preferable. , A functional group-containing monomer containing at least one monomer selected from a hydroxyl group-containing monomer and a carboxy group-containing monomer is preferable. Of these, a functional group-containing monomer having a (meth) acryloyl group is preferable. Among these, a hydroxyl group-containing monomer and a carboxy group-containing monomer are preferable because they have an excellent balance between adhesive physical properties and storage stability of the resin solution.
特に好ましい水酸基含有モノマーとしては、例えば、２−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、６−ヒドロキシヘキシル（メタ）アクリレート、８−ヒドロキシオクチル（メタ）アクリレート、１０−ヒドロキシデシル（メタ）アクリレート、１２−ヒドロキシラウリル（メタ）アクリレート等のヒドロキシアルキル（メタ）アクリレートが挙げられ、中でも重合時の安定性及び、架橋剤を使用した際の架橋効率高い点で、２−ヒドロキシエチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレートが好ましい。
特に好ましいカルボキシ基含有モノマーとしては、粘着剤とした際の凝集力が高くなる点で（メタ）アクリル酸が好ましい。
Particularly preferable hydroxyl group-containing monomers include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl. Examples thereof include hydroxyalkyl (meth) acrylates such as (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, and 12-hydroxylauryl (meth) acrylate. Of these, 2-hydroxyethyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate are preferable because of their stability during polymerization and high cross-linking efficiency when a cross-linking agent is used.
As a particularly preferable carboxy group-containing monomer, (meth) acrylic acid is preferable because it has a high cohesive force when used as a pressure-sensitive adhesive.
そして、かかる官能基含有モノマーの合計量は、アクリル系樹脂（Ａ）における重合成分全体に対して０．１〜３０重量％であることが好ましく、１〜２５重量％であることがより好ましく、３〜２０重量％であることが特に好ましい。上記官能基含有モノマーが少なすぎると、粘着剤としたときの凝集力が低下する傾向になり、多すぎると、粘着剤の保存安定性が低下したり、ポットライフが短くなったりする傾向がある。 The total amount of the functional group-containing monomers is preferably 0.1 to 30% by weight, more preferably 1 to 25% by weight, based on the total polymerization components of the acrylic resin (A). It is particularly preferably 3 to 20% by weight. If the amount of the functional group-containing monomer is too small, the cohesive force of the adhesive tends to decrease, and if it is too large, the storage stability of the adhesive tends to decrease and the pot life tends to be shortened. ..
特に官能基含有モノマーが水酸基含有モノマーである場合には、アクリル系樹脂（Ａ）における重合成分全体に対して０．１〜５０重量％であることが好ましく、特には０．１〜３０重量％、更には０．１〜１５重量％であることが好ましい。上記水酸基含有モノマーが上記範囲内であると、アクリル樹脂溶液の保存安定性と粘着剤とした際の粘着力、保持力、再剥離性のバランスに優れる傾向がある。 In particular, when the functional group-containing monomer is a hydroxyl group-containing monomer, it is preferably 0.1 to 50% by weight, particularly 0.1 to 30% by weight, based on the total polymerization components of the acrylic resin (A). Further, it is preferably 0.1 to 15% by weight. When the hydroxyl group-containing monomer is within the above range, the balance between the storage stability of the acrylic resin solution and the adhesive strength, holding power, and removability when used as a pressure-sensitive adhesive tends to be excellent.
また、カルボキシ基含有モノマーの含有量は、アクリル系樹脂（Ａ）における重合成分全体に対して０．１〜２５重量％であることが好ましく、特には０．１〜２０重量％、更には０．１〜１５重量％であることが好ましい。カルボキシ基含有モノマーが上記範囲内であると、多孔質構材料（Ｂ）の分散性と相互作用による凝集力の向上のバランスに優れる傾向にある。 The content of the carboxy group-containing monomer is preferably 0.1 to 25% by weight, particularly 0.1 to 20% by weight, and further 0, based on the total polymerization component of the acrylic resin (A). It is preferably 1 to 15% by weight. When the carboxy group-containing monomer is within the above range, the balance between the dispersibility of the porous structure material (B) and the improvement of the cohesive force due to the interaction tends to be excellent.
上記アクリル系樹脂（Ａ）を製造するに際して、その重合方法としては、例えば、溶液ラジカル重合、懸濁重合、塊状重合、乳化重合等の従来公知の方法を用いることができる。中でも、溶液ラジカル重合、塊状重合が好ましく、安定にアクリル系樹脂が得られる点で、溶液ラジカル重合が特に好ましい。 In producing the acrylic resin (A), conventionally known methods such as solution radical polymerization, suspension polymerization, bulk polymerization, and emulsion polymerization can be used as the polymerization method. Of these, solution radical polymerization and bulk polymerization are preferable, and solution radical polymerization is particularly preferable in that an acrylic resin can be stably obtained.
上記重合反応に用いられる有機溶媒としては、例えば、トルエン、キシレン等の芳香族炭化水素類、ヘキサン等の脂肪族炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、ｎ−プロピルアルコール、イソプロピルアルコール等の脂肪族アルコール類、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類等が挙げられる。これらの有機溶媒は、単独でもしくは２種以上併用することができる。 Examples of the organic solvent used in the polymerization reaction include aromatic hydrocarbons such as toluene and xylene, aliphatic hydrocarbons such as hexane, esters such as ethyl acetate and butyl acetate, n-propyl alcohol and isopropyl alcohol. Examples thereof include aliphatic alcohols such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and ketones such as cyclohexanone. These organic solvents can be used alone or in combination of two or more.
これらの有機溶媒の中でも、重合反応のしやすさや連鎖移動の効果や粘着剤組成物の塗工時の乾燥のしやすさ、安全上の点から、酢酸エチル、酢酸ブチル等のエステル類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類が好ましく、特には、酢酸エチルを含むことが好ましい。 Among these organic solvents, esters such as ethyl acetate and butyl acetate and acetone are considered from the viewpoints of ease of polymerization reaction, effect of chain transfer, ease of drying when coating the pressure-sensitive adhesive composition, and safety. , Methyl ethyl ketone, methyl isobutyl ketone and other ketones are preferable, and ethyl acetate is particularly preferable.
また、かかる溶液ラジカル重合に用いられる重合開始剤としては、通常のラジカル重合開始剤を用いることができ、例えば、２，２’−アゾビスイソブチロニトリル、２，２’−アゾビス−２−メチルブチロニトリル、４，４’−アゾビス（４−シアノ吉草酸）、２，２’−アゾビス（メチルプロピオン酸）等のアゾ系開始剤、ベンゾイルパーオキサイド、ラウロイルパーオキサイド、ジ−ｔ−ブチルパーオキサイド、クメンハイドロパーオキサイド等の有機過酸化物等が挙げられ、使用するモノマーに合わせて適宜選択して用いることができる。これらの重合開始剤は、単独でもしくは２種以上併せて用いることができる。 Further, as the polymerization initiator used for such solution radical polymerization, a usual radical polymerization initiator can be used, for example, 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-. Azo-based initiators such as methylbutyronitrile, 4,4'-azobis (4-cyanovaleric acid), 2,2'-azobis (methylpropionic acid), benzoyl peroxide, lauroyl peroxide, di-t-butyl Examples thereof include organic peroxides such as peroxide and cumenehydroperoxide, which can be appropriately selected and used according to the monomer to be used. These polymerization initiators can be used alone or in combination of two or more.
このようにして、本発明で用いられるアクリル系樹脂（Ａ）が得られる。 In this way, the acrylic resin (A) used in the present invention can be obtained.
上記アクリル系樹脂（Ａ）の重量平均分子量（Ｍｗ）は、１０万以上であることが好ましく、特に好ましくは２０万〜２００万、更に好ましくは３０万〜１５０万、殊に好ましくは４０万〜１２０万である。かかる重量平均分子量が小さすぎると、得られる粘着剤の凝集力が低下する傾向があり、保持力や再剥離性が低下する傾向にある。また、かかる重量平均分子量が大きすぎると、多孔質材料（Ｂ）によるチクソ性が高くなりすぎるため塗工しづらくなりハンドリング性が低下する傾向にある。 The weight average molecular weight (Mw) of the acrylic resin (A) is preferably 100,000 or more, particularly preferably 200,000 to 2,000,000, still more preferably 300,000 to 1,500,000, and particularly preferably 400,000 to 400,000. It is 1.2 million. If the weight average molecular weight is too small, the cohesive force of the obtained pressure-sensitive adhesive tends to decrease, and the holding force and removability tend to decrease. On the other hand, if the weight average molecular weight is too large, the thickness of the porous material (B) becomes too high, which makes it difficult to apply and tends to reduce the handleability.
また、アクリル系樹脂（Ａ）の分散度［重量平均分子量（Ｍｗ）／数平均分子量（Ｍｎ）］は、４０以下であることが好ましく、特に好ましくは３５以下、更に好ましくは３０以下である。かかる分散度が高すぎると凝集力が低下する傾向がある。なお、分散度の下限は通常１である。 The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the acrylic resin (A) is preferably 40 or less, particularly preferably 35 or less, and even more preferably 30 or less. If the degree of dispersion is too high, the cohesive force tends to decrease. The lower limit of the degree of dispersion is usually 1.
上記のアクリル系樹脂（Ａ）の重量平均分子量は、標準ポリスチレン分子量換算による重量平均分子量であり、高速液体クロマトグラフ（日本Ｗａｔｅｒｓ社製、「Ｗａｔｅｒｓ ２６９５（本体）」と「Ｗａｔｅｒｓ ２４１４（検出器）」）に、カラム：Ｓｈｏｄｅｘ ＧＰＣ ＫＦ−８０６Ｌ（排除限界分子量：２×１０７、分離範囲：１００〜２×１０７、理論段数：１０，０００段／本、充填剤材質：スチレン−ジビニルベンゼン共重合体、充填剤粒径：１０μｍ）を３本直列に接続して用いることにより測定されるものであり、数平均分子量も同様の方法で測定することができる。また分散度は、上記重量平均分子量と数平均分子量の測定値より求めることができる。 The weight average molecular weight of the acrylic resin (A) is the weight average molecular weight converted to the standard polystyrene molecular weight, and is a high-speed liquid chromatograph (manufactured by Japan Waters, "Waters 2695 (main body)" and "Waters 2414 (detector)". ”), Column: Shodex GPC KF-806L (exclusion limit molecular weight: 2 × 10 7 , separation range: 100 to 2 × 10 7 , theoretical number of stages: 10,000 stages / piece, filler material: styrene-divinylbenzene) It is measured by connecting three polymers (polymer, filler particle size: 10 μm) in series and using them, and the number average molecular weight can also be measured by the same method. The degree of dispersion can be obtained from the measured values of the weight average molecular weight and the number average molecular weight.
上記アクリル系樹脂（Ａ）のガラス転移温度（Ｔｇ）は、０℃以下であることが必要であり、より好ましくは−１００〜−１０℃、特に好ましくは−７０〜−３０℃である。かかるガラス転移温度が高すぎると、粘着剤とした際にタックの低下が大きくなる傾向がある。 The glass transition temperature (Tg) of the acrylic resin (A) needs to be 0 ° C. or lower, more preferably −100 to −10 ° C., and particularly preferably −70 to −30 ° C. If the glass transition temperature is too high, the tack tends to be significantly reduced when the adhesive is used.
なお、上記ガラス転移温度（Ｔｇ）は、アクリル系樹脂（Ａ）を構成するそれぞれのモノマーをホモポリマーとした際のガラス転移温度および重量分率を、下記のＦｏｘの式に当てはめて算出した値である。
ここで、アクリル系樹脂（Ａ）を構成するモノマーをホモポリマーとした際のガラス転移温度は、通常、示差走査熱量計（ＤＳＣ）により測定されるものであり、ＪＩＳ Ｋ ７１２１−１９８７や、ＪＩＳ Ｋ ６２４０に準拠した方法で測定することができる。
The glass transition temperature (Tg) is a value calculated by applying the glass transition temperature and weight fraction when each monomer constituting the acrylic resin (A) is homopolymer to the following Fox formula. Is.
Here, the glass transition temperature when the monomer constituting the acrylic resin (A) is homopolymer is usually measured by a differential scanning calorimeter (DSC), and is measured by JIS K 7121-1987 or JIS. It can be measured by a method conforming to K 6240.
Tga ：モノマーＡのホモポリマーのガラス転移温度（Ｋ）
Wa ：モノマーＡの重量分率
Tgb ：モノマーＢのホモポリマーのガラス転移温度（Ｋ）
Wb ：モノマーＢの重量分率
Tgn ：モノマーＮのホモポリマーのガラス転移温度（Ｋ）
Wn ：モノマーＮの重量分率
（Wa＋Wb＋…＋Wn＝１）
Tga: Glass transition temperature (K) of homopolymer of monomer A
Wa: Weight fraction of monomer A
Tgb: Glass transition temperature (K) of homopolymer of monomer B
Wb: Weight fraction of monomer B
Tgn: Glass transition temperature (K) of homopolymer of monomer N
Wn: Weight fraction of monomer N (Wa ＋ Wb ＋… ＋ Wn ＝ 1)
＜多孔質材料（Ｂ）＞
本発明で用いる多孔質材料（Ｂ）は、細孔を多く有する多孔質構造の物質であり、例えば、ゼオライト、活性炭、メソポーラスシリカ、シリカゲル、等があげられる。
細孔は直径の大きさによって２ｎｍ以下のミクロポーラス、２ｎｍ〜５０ｎｍのメソポーラス、５０ｎｍ以上のマクロポーラスと分類される。
本発明においては、ミクロポーラス、メソポーラス構造を有する物質が吸着性の点で好ましく、なかでもシリカゲルやゼオライト、活性炭がより好ましく、特には細孔の大きさの幅が広く様々な分子に対して吸着性能を示す活性炭が好ましい。
活性炭は植物由来の材料が炭素利用の点で好ましく、ヤシ殻やもみ殻、バガスなどが好ましい。
<Porous medium (B)>
The porous material (B) used in the present invention is a substance having a porous structure having many pores, and examples thereof include zeolite, activated carbon, mesoporous silica, and silica gel.
The pores are classified into microporous 2 nm or less, mesoporous 2 nm to 50 nm, and macroporous 50 nm or more according to the size of the diameter.
In the present invention, substances having microporous and mesoporous structures are preferable in terms of adsorptivity, among which silica gel, zeolite, and activated carbon are more preferable, and in particular, they have a wide pore size and are adsorbed on various molecules. Activated carbon showing performance is preferable.
As the activated carbon, a plant-derived material is preferable in terms of carbon utilization, and coconut husks, rice husks, bagasse and the like are preferable.
上記多孔質材料（Ｂ）の平均粒径が０．０１〜１００μｍであることが好ましく、特には０．０５〜５０μｍ、更には０．１〜２５μｍであることが好ましい。かかる平均粒径が大きすぎると、粘着剤層とした際に表面の平滑性が低下し、部材と接触しにくくなる傾向があり、小さすぎるとチクソ性が高くなったり粉塵によるハンドリング性が低下したりする傾向がある。 The average particle size of the porous material (B) is preferably 0.01 to 100 μm, particularly preferably 0.05 to 50 μm, and further preferably 0.1 to 25 μm. If the average particle size is too large, the smoothness of the surface is lowered when the pressure-sensitive adhesive layer is formed, and it tends to be difficult to come into contact with the member. There is a tendency to do.
多孔質材料（Ｂ）の含有量は、粘着性樹脂（Ａ）１００重量部に対して１〜２００重量部であることが好ましく、特には５〜１５０重量部が好ましく、更には１０〜１００重量部が好ましい。かかる含有量が多すぎると、粘着剤とした際のタックが低下する傾向があり、少なすぎると吸着性能が低下する傾向がある。 The content of the porous material (B) is preferably 1 to 200 parts by weight, particularly preferably 5 to 150 parts by weight, and further 10 to 100 parts by weight with respect to 100 parts by weight of the adhesive resin (A). Part is preferable. If the content is too large, the tackiness when used as an adhesive tends to decrease, and if it is too small, the adsorption performance tends to decrease.
＜架橋剤（Ｃ）＞
本発明の粘着剤組成物は、粘着性樹脂（Ａ）の架橋を目的とした架橋剤（Ｃ）を使用することが好ましい。架橋剤（Ｃ）を使用することで、粘着剤の凝集力を高め、保持力や再剥離性を向上させることができる点で好適である。
<Crosslinking agent (C)>
In the pressure-sensitive adhesive composition of the present invention, it is preferable to use a cross-linking agent (C) for the purpose of cross-linking the pressure-sensitive adhesive resin (A). By using the cross-linking agent (C), the cohesive force of the pressure-sensitive adhesive can be increased, and the holding power and the removability can be improved, which is preferable.
架橋剤（Ｃ）は、粘着性樹脂（Ａ）と反応できる官能基を２個以上有する化合物であればよく、例えば、イソシアネート系架橋剤、エポキシ系架橋剤、キレート系架橋剤、アミン系架橋剤、酸無水物系架橋剤、アジリジン系架橋剤、カルボジイミド系架橋剤等があげられる。これらの中でも、粘着物性のバランスに優れる点、エージングが早い点でイソシアネート系架橋剤、エポキシ系架橋剤、キレート系架橋剤が好ましい。 The cross-linking agent (C) may be a compound having two or more functional groups capable of reacting with the adhesive resin (A), and may be, for example, an isocyanate-based cross-linking agent, an epoxy-based cross-linking agent, a chelate-based cross-linking agent, or an amine-based cross-linking agent. , Acid anhydride type cross-linking agent, aziridine-based cross-linking agent, carbodiimide-based cross-linking agent and the like. Among these, isocyanate-based cross-linking agents, epoxy-based cross-linking agents, and chelate-based cross-linking agents are preferable in terms of excellent balance of adhesive properties and quick aging.
上記イソシアネート系架橋剤としては、例えば、２，４−トリレンジイソシアネート、２，６−トリレンジイソシアネート等のトリレンジイソシアネート系架橋剤、１，３−キシリレンジイソシアネート等のキシリレンジイソシアネート系架橋剤、ジフェニルメタン−４，４−ジイソシアネート等のジフェニルメタン系架橋剤、１，５−ナフタレンジイソシアネート等のナフタレンジイソシアネート系架橋剤等の芳香族系イソシアネート系架橋剤；イソホロンジイソシアネート、１，４−シクロヘキサンジイソシアネート、４，４’−ジシクロヘキシルメタンジイソシアネート、メチルシクロヘキサンジイソシアネート、イソプロピリデンジシクロヘキシル−４，４’−ジイソシアネート、１，３−ジイソシアナトメチルシクロヘキサン、ノルボルナンジイソシアネート等の脂環族系イソシアネート系架橋剤；ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート等の脂肪族系イソシアネート系架橋剤；及び上記イソシアネート系化合物のアダクト体、ビュレット体、イソシアヌレート体等が挙げられる。 Examples of the isocyanate-based cross-linking agent include a tolylene diisocyanate-based cross-linking agent such as 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate, and a xylylene diisocyanate-based cross-linking agent such as 1,3-xylylene diisocyanate. Diphenylmethane-based cross-linking agents such as diphenylmethane-4,4-diisocyanate, aromatic isocyanate-based cross-linking agents such as naphthalene diisocyanate such as 1,5-naphthalenediocyanate; isophorone diisocyanate, 1,4-cyclohexanediisocyanate, 4,4 Alicyclic isocyanate-based cross-linking agents such as'-dicyclohexylmethane diisocyanate, methylcyclohexanediisocyanate, isopropyridendicyclohexyl-4,4'-diisocyanate, 1,3-diisocyanatomethylcyclohexane, norbornandiisocyanate; Examples thereof include aliphatic isocyanate-based cross-linking agents such as methylene diisocyanate; and adducts, bullets, and isocyanurates of the isocyanate-based compounds.
これらイソシアネート系架橋剤のなかでも、トリレンジイソシアネート系架橋剤がポットライフと耐久性の点で好ましく、キシリレンジイソシアネート系架橋剤またはイソシアヌレート骨格含有イソシアネート系架橋剤がエージング時間短縮の点で好ましく、非芳香族非含有イソシアネート系架橋剤が耐黄変性の点で好ましい。これらの中で具体的には、トリレンジイソシアネート、キシリレンジイソシアネート、ヘキサメチレンジイソシアネートとトリメチロールプロパンのアダクト体、及びヌレート体が、耐久性、ポットライフ、架橋速度のバランスに優れている点で好ましい。 Among these isocyanate-based cross-linking agents, a tolylene diisocyanate-based cross-linking agent is preferable in terms of pot life and durability, and a xylylene diisocyanate-based cross-linking agent or an isocyanurate skeleton-containing isocyanate-based cross-linking agent is preferable in terms of shortening the aging time. A non-aromatic non-containing isocyanate cross-linking agent is preferable in terms of yellowing resistance. Among these, specifically, tolylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate and trimethylolpropane adduct, and nucleohydrate are preferable because they have an excellent balance of durability, pot life, and cross-linking rate. ..
上記エポキシ系架橋剤としては、例えば、ビスフェノールＡ・エピクロルヒドリン型のエポキシ樹脂、エチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、グリセリンジグリシジルエーテル、グリセリントリグリシジルエーテル、１，６−ヘキサンジオールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ソルビトールポリグリシジルエーテル、ポリグリセロールポリグリシジルエーテル、ペンタエリスリトールポリグリシジルエリスリトール、ジグリセロールポリグリシジルエーテル等が挙げられる。 Examples of the epoxy-based cross-linking agent include bisphenol A / epichlorohydrin type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, and 1,6-hexanediol diglycidyl ether. , Trimethylol propan triglycidyl ether, sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl erythritol, diglycerol polyglycidyl ether and the like.
上記金属キレート系架橋剤としては、例えば、アルミニウム、鉄、銅、亜鉛、スズ、チタン、ニッケル、アンチモン、マグネシウム、パナジウム、クロム、ジルコニウム等の多価金属のアセチルアセトンやアセトアセチルエステル配位化合物等が挙げられる。 Examples of the metal chelate-based cross-linking agent include acetylacetone and acetoacetyl ester coordination compounds of polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, panadium, chromium and zirconium. Can be mentioned.
上記アミン系架橋剤としては、例えば、ヘキサメチレンジアミン、トリエチルジアミン、ポリエチレンイミン、ヘキサメチレンテトラアミン、ジエチレントリアミン、トリエチルテトラアミン、イソフォロンジアミン、アミノ樹脂、ポリアミド等が挙げられる。 Examples of the amine-based cross-linking agent include hexamethylenediamine, triethyldiamine, polyethyleneimine, hexamethylenetetraamine, diethylenetriamine, triethyltetraamine, isophoronediamine, amino resin, and polyamide.
上記アジリジン系架橋剤としては、例えば、テトラメチロールメタン−トリ−β−アジリジニルプロピオネート、トリメチロールプロパン−トリ−β−アジリジニルプロピオネート、Ｎ，Ｎ’−ジフェニルメタン−４，４’−ビス（１−アジリジンカルボキシアミド）、Ｎ，Ｎ’−ヘキサメチレン−１，６−ビス（１−アジリジンカルボキシアミド）等が挙げられる。 Examples of the aziridine-based cross-linking agent include tetramethylolmethane-tri-β-aziridinyl propionate, trimethylolpropane-tri-β-aziridinyl propionate, and N, N'-diphenylmethane-4,4. ′ -Bis (1-aziridine carboxamide), N, N'-hexamethylene-1,6-bis (1-aziridine carboxamide) and the like can be mentioned.
カルボジイミド系架橋剤としては、例えば、多官能型カルボジイミドがあげられ、市販品としては、日清紡ケミカル社製、カルボジライト「Ｖ−０３」「Ｖ−０４」「Ｖ−０９」等があげられる。 Examples of the carbodiimide-based cross-linking agent include polyfunctional carbodiimide, and examples of commercially available products include carbodilites "V-03", "V-04", and "V-09" manufactured by Nisshinbo Chemical Co., Ltd.
上記架橋剤（Ｃ）は、単独で使用してもよいし、２種以上を併用してもよい。 The above-mentioned cross-linking agent (C) may be used alone or in combination of two or more.
上記架橋剤（Ｃ）の含有量は、粘着性樹脂（Ａ）１００重量部に対して０．０１〜２０重量部であることが好ましく、より好ましくは０．０５〜１５重量部、特に好ましくは０．１〜１０重量部である。上記範囲にあれば、粘着力や保持力や再剥離性のバランスにより優れた粘着剤となる。 The content of the cross-linking agent (C) is preferably 0.01 to 20 parts by weight, more preferably 0.05 to 15 parts by weight, and particularly preferably 0.05 parts by weight with respect to 100 parts by weight of the adhesive resin (A). 0.1 to 10 parts by weight. If it is within the above range, it becomes an excellent adhesive due to the balance of adhesive strength, holding power and removability.
本発明に用いられる粘着剤組成物には、本発明の効果を損なわない範囲において、各種の任意成分を配合することができる。以下、それらの任意成分について説明する。 The pressure-sensitive adhesive composition used in the present invention may contain various arbitrary components as long as the effects of the present invention are not impaired. Hereinafter, these optional components will be described.
＜その他の任意成分＞
その他の任意成分としては、例えば、カーボンや金属等の導電剤；金属粒子やガラス粒子等の無機フィラー；ウレタン樹脂、ロジン、ロジンエステル、水添ロジンエステル、フェノール樹脂、脂肪族系石油樹脂、脂環族系石油樹脂、スチレン系樹脂等の粘着付与剤；充填剤；酸化防止剤；紫外線吸収剤；紫外線安定剤；シランカップリング剤；イオン性化合物、過酸化物、ウレタン化触媒等の架橋促進剤；アセチルアセトン等の架橋遅延剤；顔料；等の各種添加剤が挙げられる。
<Other optional ingredients>
Other optional components include, for example, conductive agents such as carbon and metal; inorganic fillers such as metal particles and glass particles; urethane resin, rosin, rosin ester, hydrogenated rosin ester, phenol resin, aliphatic petroleum resin, fat. Adhesive-imparting agents such as ring-based petroleum resins and styrene-based resins; fillers; antioxidants; ultraviolet absorbers; ultraviolet stabilizers; silane coupling agents; promoting cross-linking of ionic compounds, peroxides, esterification catalysts, etc. Agents; cross-linking retardants such as acetylacetone; pigments; various additives such as.
また、上記添加剤の他にも、粘着剤組成物の構成成分の製造原料等に含まれる不純物等が少量含有されたものであってもよい。 In addition to the above additives, a small amount of impurities and the like contained in the raw materials for producing the constituent components of the pressure-sensitive adhesive composition may be contained.
かくして本発明の粘着性樹脂（Ａ）及び多孔質材料（Ｂ）、好ましくは更に架橋剤（Ｃ）、必要に応じて更にその他添加剤を含有する粘着剤組成物が得られるが、配合方法については、特に限定されず、一括で仕込んでもよいし、任意の成分を混合した後、残りの成分を一括または順次混合する方法等、種々の方法を採用することができる。 Thus, a pressure-sensitive adhesive composition containing the pressure-sensitive adhesive resin (A) and the porous material (B) of the present invention, preferably a cross-linking agent (C), and if necessary, other additives can be obtained. Is not particularly limited, and may be charged in a batch, or various methods such as a method in which arbitrary components are mixed and then the remaining components are mixed in a batch or sequentially can be adopted.
本発明の粘着剤組成物をプラスチックフィルム等の基材に積層形成することにより、粘着シートを得ることができる。
なお、本発明において、「シート」とは、特に「フィルム」、「テープ」と区別するものではなく、これらも含めた意味として記載するものである。
A pressure-sensitive adhesive sheet can be obtained by laminating and forming the pressure-sensitive adhesive composition of the present invention on a base material such as a plastic film.
In the present invention, the term "sheet" is not particularly distinguished from "film" and "tape", but is described as a meaning including these.
上記粘着シートの製造方法としては、例えば、セパレータや基材上に、粘着剤組成物を塗工、乾燥した後、セパレータ（セパレータに塗工した場合は剥離力の異なるセパレータ）を貼合したり、自背面に巻き取る方法がある。 As a method for producing the above-mentioned adhesive sheet, for example, an adhesive composition is applied onto a separator or a base material, dried, and then a separator (a separator having a different peeling force when applied to the separator) is attached. , There is a way to wind it up on its own back.
上記粘着剤組成物の塗工に際しては、この粘着剤組成物を溶剤で希釈して塗工することが好ましく、希釈した場合の固形分濃度は、好ましくは５〜８０重量％、特に好ましくは２０〜６０重量％である。また、上記溶剤としては、粘着剤組成物が分離しないものであれば特に限定されない。例えば、酢酸メチル、酢酸エチル、アセト酢酸メチル、アセト酢酸エチル等のエステル系溶剤、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶剤、トルエン、キシレン等の芳香族系溶剤、メタノール、エタノール、プロピルアルコール等のアルコール系溶剤を用いることができる。これらの中でも、溶解性、乾燥性、塗工適正の点で酢酸エチル、メチルエチルケトン、アセトン、トルエンが好適に用いられる。 When applying the pressure-sensitive adhesive composition, it is preferable to dilute the pressure-sensitive adhesive composition with a solvent before coating, and the solid content concentration when diluted is preferably 5 to 80% by weight, particularly preferably 20. ~ 60% by weight. The solvent is not particularly limited as long as the pressure-sensitive adhesive composition does not separate. For example, ester solvents such as methyl acetate, ethyl acetate, methyl acetoacetate, ethyl acetoacetate, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone, aromatic solvents such as toluene and xylene, methanol, ethanol and propyl alcohol. Alcohol-based solvents such as, etc. can be used. Among these, ethyl acetate, methyl ethyl ketone, acetone, and toluene are preferably used in terms of solubility, drying property, and coating suitability.
上記塗工に供する粘着剤組成物の粘度は、１００〜１５０００ｍＰａ・ｓ／２５℃が好ましく、１０００〜１００００ｍＰａ・ｓ／２５℃がより好ましい。粘度が低すぎると比重の大きい成分を用いた場合、その成分が沈降しやすくなる傾向があり、粘度が高すぎると均一塗工が困難となる傾向がある。 The viscosity of the pressure-sensitive adhesive composition to be applied to the coating is preferably 100 to 15000 mPa · s / 25 ° C, more preferably 1000 to 10000 mPa · s / 25 ° C. If the viscosity is too low, when a component having a large specific gravity is used, the component tends to settle easily, and if the viscosity is too high, uniform coating tends to be difficult.
また、上記粘着剤組成物の塗工方法としては、例えば、ロールコーティング、ダイコーティング、グラビアコーティング、コンマコーティング、スクリーン印刷等の方法が挙げられる。 In addition, examples of the coating method of the pressure-sensitive adhesive composition include methods such as roll coating, die coating, gravure coating, comma coating, and screen printing.
粘着剤組成物を塗布した後、乾燥させることにより、基材上に粘着剤層が形成される。乾燥温度は、特に限定されるものではないが、加熱乾燥時に架橋反応が進行するので、架橋剤（Ｃ）の種類に応じて架橋反応が速やかに進行する温度で乾燥することが好ましい。 A pressure-sensitive adhesive layer is formed on the base material by applying the pressure-sensitive adhesive composition and then drying it. The drying temperature is not particularly limited, but since the cross-linking reaction proceeds during heat-drying, it is preferable to dry at a temperature at which the cross-linking reaction proceeds rapidly depending on the type of the cross-linking agent (C).
また、架橋剤を用いる場合には、室温（２３℃）及び加温状態の少なくとも一方によるエージング処理を行ってもよい。エージングの条件としては、温度は通常、室温〜４０℃、時間は通常１〜３０日間であり、具体的には、例えば２３℃で１〜２０日間、４０℃で１〜７日間等の条件で行えばよい。 When a cross-linking agent is used, the aging treatment may be performed at at least one of room temperature (23 ° C.) and a heated state. As the aging conditions, the temperature is usually room temperature to 40 ° C., and the time is usually 1 to 30 days. Specifically, for example, 23 ° C. for 1 to 20 days, 40 ° C. for 1 to 7 days, and the like. Just do it.
本発明において、得られる粘着剤のゲル分率は、用途に応じて調整すればよく、部材との密着性、リワーク性、保持力の点から５〜１００重量％であることが好ましく、粘着力と保持力バランスを考慮した場合は、５〜９５重量％が好ましく、１５〜９０重量％が好ましく、４０〜８５％が特に好ましい。
表面保護用に用いる場合は、６０−１００重量％が好ましく、８０〜１００重量％が好ましく、９０〜１００重量％がさらに好ましい。
上記粘着剤のゲル分率が低すぎると、凝集力が低くなり、再剥離性や保持力が低下する傾向にあり、高すぎるとタックが低下したり、粘着力が低くなりすぎる傾向にある。
In the present invention, the gel fraction of the obtained pressure-sensitive adhesive may be adjusted according to the intended use, and is preferably 5 to 100% by weight in terms of adhesion to the member, reworkability, and holding power, and the pressure-sensitive adhesive force. When the holding power balance is taken into consideration, 5 to 95% by weight is preferable, 15 to 90% by weight is preferable, and 40 to 85% is particularly preferable.
When used for surface protection, it is preferably 60 to 100% by weight, preferably 80 to 100% by weight, and even more preferably 90 to 100% by weight.
If the gel fraction of the pressure-sensitive adhesive is too low, the cohesive force tends to be low, and the removability and holding power tend to be low, and if it is too high, the tack tends to be low and the adhesive strength tends to be too low.
上記ゲル分率は、架橋度（硬化度合い）の目安となるもので、例えば、以下の方法にて算出される。即ち、基材等の表面に粘着剤層が形成されてなる粘着シートから粘着剤をピッキングにより採取する。この採取した粘着剤を２００メッシュのＳＵＳ製金網で包み、２３℃に調整した酢酸エチル中に２４時間浸漬し、浸漬前の粘着剤成分の重量に対する、浸漬後の金網中に残存した不溶解の粘着剤成分の重量百分率をゲル分率とする。 The gel fraction is a measure of the degree of cross-linking (degree of curing), and is calculated by, for example, the following method. That is, the pressure-sensitive adhesive is collected by picking from the pressure-sensitive adhesive sheet in which the pressure-sensitive adhesive layer is formed on the surface of the base material or the like. The collected adhesive was wrapped in a 200 mesh SUS wire mesh and immersed in ethyl acetate adjusted to 23 ° C. for 24 hours to allow the insoluble material remaining in the wire mesh after immersion with respect to the weight of the adhesive component before immersion. The weight percentage of the pressure-sensitive adhesive component is defined as the gel fraction.
本発明において、粘着剤からなる粘着剤層の厚みは、特に限定されないが、粘着力と剥離性の点で、５〜２５０μｍが好ましく、特には１０〜２００μｍ、更には１５〜１００μｍであることが好ましい。また、厚すぎると、乾燥時に粘着剤層表面に発泡が生じたり、溶剤が残留しやすくなる傾向があり、薄すぎると粘着力が低下したり、粘着シートの単位面積当たりの多孔質材料（Ｂ）の量が少なくなり吸着性能が低下する傾向にある。 In the present invention, the thickness of the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive is not particularly limited, but is preferably 5 to 250 μm, particularly 10 to 200 μm, and further 15 to 100 μm in terms of adhesive strength and peelability. preferable. Further, if it is too thick, foaming tends to occur on the surface of the pressure-sensitive adhesive layer during drying, and the solvent tends to remain, and if it is too thin, the adhesive strength decreases, or the porous material per unit area of the pressure-sensitive adhesive sheet (B). ) Tends to decrease and the adsorption performance tends to decrease.
また、粘着剤層の厚みが多孔性材料（Ｂ）の平均粒径の値に対して０．９〜２００倍であることが好ましく、より好ましくは１〜１００倍、更に好ましくは１．１〜５０倍である。粘着剤層の厚みが上記範囲から外れると表面に凹凸形状が生じてしまい表面外観が低下する傾向にある。 Further, the thickness of the pressure-sensitive adhesive layer is preferably 0.9 to 200 times, more preferably 1 to 100 times, still more preferably 1.1 to 100 times the value of the average particle size of the porous material (B). It is 50 times. If the thickness of the pressure-sensitive adhesive layer deviates from the above range, an uneven shape is formed on the surface, and the surface appearance tends to be deteriorated.
なお、上記の基材としては、例えば、上質紙、クラフト紙、クレープ紙、グラシン紙等の従来公知の紙類、ポリエチレン、ポリプロピレン、ポリエステル、ポリスチレン、ポリエチレンテレフタレート、ポリ塩化ビニル、セロファン等のプラスチック、織布、不織布等の繊維製品等を利用することができる。基材の形状は、例えば、フィルム状、シート状、テープ状、板状等が挙げられ、これらの性状としては発泡体でもよく、特に限定されるものではない。基材の片面に粘着剤組成物を公知の方法によって塗布することによって、粘着シート、粘着ラベル等を得ることができる。 Examples of the above-mentioned base material include conventionally known papers such as high-quality paper, kraft paper, crepe paper, and glass paper, and plastics such as polyethylene, polypropylene, polyester, polystyrene, polyethylene terephthalate, polyvinyl chloride, and cellophane. Textile products such as woven cloth and non-woven fabric can be used. Examples of the shape of the base material include a film shape, a sheet shape, a tape shape, a plate shape, and the like, and these properties may be a foam, and are not particularly limited. By applying the pressure-sensitive adhesive composition to one side of the base material by a known method, a pressure-sensitive adhesive sheet, a pressure-sensitive adhesive label, or the like can be obtained.
以下、実施例を挙げて本発明を更に具体的に説明するが、本発明はその要旨を超えない限り以下の実施例に限定されるものではない。
尚、例中「部」、「％」とあるのは、重量基準を意味する。
また、下記実施例中におけるアクリル系樹脂の重量平均分子量、分散度、粘着剤層のゲル分率は、前述の方法に従って測定した。
アクリル系樹脂のガラス転移温度についてはＦｏｘの式を用いて算出し、アクリル系樹脂を構成するモノマーのホモポリマーとした際のガラス転移温度は通常ＤＳＣにより測定されてなる文献値及びカタログ記載値を用いた。
まず、実施例に先立って下記の成分を準備した。
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded.
In the example, "part" and "%" mean a weight standard.
In addition, the weight average molecular weight, the degree of dispersion, and the gel fraction of the pressure-sensitive adhesive layer of the acrylic resin in the following examples were measured according to the above-mentioned method.
The glass transition temperature of the acrylic resin is calculated using the Fox formula, and the glass transition temperature when a homopolymer of the monomers constituting the acrylic resin is used is the literature value and the value described in the catalog, which are usually measured by DSC. Using.
First, the following components were prepared prior to the examples.
＜粘着性樹脂（Ａ）＞
粘着性樹脂として、アクリル系樹脂（Ａ−１）を用意した。
［アクリル系樹脂（Ａ−１）の調製］
還流冷却器、撹拌器、窒素ガスの吹き込み口及び温度計を備えた４ツ口丸底フラスコに、酢酸エチル２５．８部、アセトン１２．２部、重合開始剤としてアゾビスイソブチロニトリル（ＡＩＢＮ）を０．００７５部仕込み、加熱して内温が沸点に到達した後、２−エチルヘキシルアクリレート（２ＥＨＡ）９２．８部、アクリル酸（ＡＡｃ）０．２部、２−ヒドロキシエチルアクリレート（２ＨＥＡ）５部、酢酸エチル３．３部、重合開始剤０．０３部の混合溶液を２時間にわたって滴下した。滴下開始から２．７５時間後にトルエン１０部と２ＨＥＡ１部、３．２５時間後にトルエン１０部と重合開始剤（ＡＩＢＮ）０．０３６部、４．７５時間後にトルエン１０部と２ＨＥＡ１部、５．２５時間後にトルエン１０部とＡＩＢＮ０．０６部を順次追加しながら反応を継続させ７．２５時間後に酢酸エチルとトルエンで希釈してアクリル系樹脂（Ａ−１）溶液（樹脂分３９．８％、粘度７４００、重量平均分子量１１４万、分散度７．７、ガラス転移温度−６６．７℃）を得た。
<Adhesive resin (A)>
An acrylic resin (A-1) was prepared as the adhesive resin.
[Preparation of acrylic resin (A-1)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 25.8 parts of ethyl acetate, 12.2 parts of acetone, and azobisisobutyronitrile as a polymerization initiator ( After 0.0075 parts of AIBN) is charged and heated to reach the boiling point, 92.8 parts of 2-ethylhexyl acrylate (2EHA), 0.2 parts of acrylic acid (AAc), and 2-hydroxyethyl acrylate (2HEA) ) 5 parts, 3.3 parts of ethyl acetate and 0.03 part of the polymerization initiator were added dropwise over 2 hours. 2.75 hours after the start of dropping, 10 parts of toluene and 1 part of 2HEA, 3.25 hours later, 10 parts of toluene and 0.036 part of the polymerization initiator (AIBN), 4.75 hours later, 10 parts of toluene and 1 part of 2HEA, 5.25. After an hour, the reaction was continued while adding 10 parts of toluene and 0.06 part of AIBN in sequence, and after 7.25 hours, the mixture was diluted with ethyl acetate and toluene to form an acrylic resin (A-1) solution (resin content 39.8%, viscosity). 7400, a weight average molecular weight of 1.14 million, a degree of dispersion of 7.7, and a glass transition temperature of −66.7 ° C.) were obtained.
＜多孔質材料（Ｂ）＞
多孔質材料（Ｂ）として以下のものを用意した。
（Ｂ−１）ヤシ殻活性炭（製品名：ＫＤ−ＰＷＳＰ 株式会社ユー・イー・エス社製）平均径６．１６２μｍ 最大径１２．９９μｍ
<Porous medium (B)>
The following materials were prepared as the porous material (B).
(B-1) Palm shell activated carbon (Product name: KD-PWSP, manufactured by US Corporation) Average diameter 6.162 μm Maximum diameter 12.99 μm
＜架橋剤（Ｃ）＞
架橋剤（Ｃ）として、以下のものを用いた。
（Ｃ−１）トリレンジイソシアネートとトリメチロールプロパンのアダクト体（東ソー社製、「コロネートＬ５５Ｅ」）
<Crosslinking agent (C)>
The following was used as the cross-linking agent (C).
(C-1) Adducts of tolylene diisocyanate and trimethylolpropane (manufactured by Tosoh Corporation, "Coronate L55E")
（実施例１〜４、比較例１）
多孔質材料（Ｂ−１）を酢酸エチルで希釈し１０％分散液を調整した。得られた分散液を有効成分比が表１となるように、アクリル系樹脂（Ａ−１）溶液に追加し、ディスパーで充分に撹拌した。次いで、架橋剤（Ｃ−１）を表１の含有割合となるように加え、有効成分が３０％となるように酢酸エチルで希釈して、更に充分に撹拌して粘着剤組成物を得た。
得られた粘着剤組成物を３８μｍポリエチレンテレフタレート（ＰＥＴ）フィルムに乾燥後の厚みが５０μｍとなるように塗工し、１００℃で１５分間乾燥し、粘着剤層を有する粘着シートを得た。
得られた粘着シートの粘着剤層表面に３８μｍシリコーンセパレーター（三井東セロ社製ＳＰ０１３８ＢＵ）を貼合し、４０℃、３日間エージングを行った。
得られた粘着シートについて、以下の評価を行った。評価結果を表１に示す。
(Examples 1 to 4, Comparative Example 1)
The porous material (B-1) was diluted with ethyl acetate to prepare a 10% dispersion. The obtained dispersion was added to the acrylic resin (A-1) solution so that the active ingredient ratio was shown in Table 1, and the mixture was sufficiently stirred with a disper. Next, the cross-linking agent (C-1) was added so as to have the content ratio shown in Table 1, diluted with ethyl acetate so that the active ingredient was 30%, and further sufficiently stirred to obtain a pressure-sensitive adhesive composition. ..
The obtained pressure-sensitive adhesive composition was applied to a 38 μm polyethylene terephthalate (PET) film so that the thickness after drying was 50 μm, and dried at 100 ° C. for 15 minutes to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer.
A 38 μm silicone separator (SP0138BU manufactured by Mitsui Tosero Co., Ltd.) was attached to the surface of the pressure-sensitive adhesive layer of the obtained pressure-sensitive adhesive sheet, and aged at 40 ° C. for 3 days.
The obtained adhesive sheet was evaluated as follows. The evaluation results are shown in Table 1.
（粘着力）
上記粘着シートを幅２５ｍｍ×長さ１００ｍｍに裁断し、シリコーンセパレーターを剥離して、粘着剤層側を被着体（ＳＵＳ−ＢＡ板）に２３℃、相対湿度５０％の雰囲気下で２ｋｇゴムローラーを２往復して加圧貼付し、同雰囲気下で１日静置した後、引張試験機（島津オートグラフＡＧ−Ｘ）を用いて、剥離速度３００ｍｍ／ｍｉｎで１８０度剥離強度（Ｎ／２５ｍｍ）を測定した。
(Adhesive force)
The adhesive sheet is cut into a width of 25 mm and a length of 100 mm, the silicone separator is peeled off, and the adhesive layer side is placed on an adherend (SUS-BA plate) at 23 ° C. and a 2 kg rubber roller in an atmosphere of 50% relative humidity. 2 reciprocations and pressure sticking, and after allowing to stand in the same atmosphere for 1 day, 180 degree peel strength (N / 25 mm) at a peeling speed of 300 mm / min using a tensile tester (Shimadzu Autograph AG-X). ) Was measured.
（脱臭効果試験）
市販の養生テープを２種類（α、β）（アクリル系粘着剤）用意した。養生テープの粘着剤層全面に、上記で得られた粘着シートの粘着剤層全面を貼合し、２３℃で３日間静置した。静置後、粘着シートを剥離し、養生テープの粘着剤層面の臭気を下記の基準で判定した。
＜評価基準＞
○・・・被験者３名のうち、３名とも臭気を感じない
△・・・被験者３名のうち、１名または２名が臭気を感じる
×・・・被験者３名のうち、３名とも臭気を感じる
(Deodorizing effect test)
Two types of commercially available curing tapes (α, β) (acrylic adhesive) were prepared. The entire surface of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet obtained above was attached to the entire surface of the pressure-sensitive adhesive layer of the curing tape, and the mixture was allowed to stand at 23 ° C. for 3 days. After standing, the adhesive sheet was peeled off, and the odor of the adhesive layer surface of the curing tape was judged according to the following criteria.
<Evaluation criteria>
○ ・ ・ ・ 3 out of 3 subjects do not feel odor △ ・ ・ ・ 1 or 2 out of 3 subjects feel odor × ・ ・ ・ 3 out of 3 subjects have odor Feel
（残存モノマー低減効果）
市販の養生テープを２種類（α、β）（アクリル系粘着剤）用意した。養生テープの粘着剤層全面に、上記で得られた粘着シートの粘着剤層全面を貼合し、２３℃×２か月間静置した後、粘着シートを剥離し、養生テープに含まれる残存モノマー（２ＥＨＡ）を下記の測定方法にて測定した。評価基準は以下の通りである。
(Remaining monomer reduction effect)
Two types of commercially available curing tapes (α, β) (acrylic adhesive) were prepared. The entire surface of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet obtained above is attached to the entire surface of the pressure-sensitive adhesive layer of the curing tape, and after allowing to stand at 23 ° C. for 2 months, the pressure-sensitive adhesive sheet is peeled off and the residual monomer contained in the curing tape is removed. (2EHA) was measured by the following measuring method. The evaluation criteria are as follows.
（測定方法）
上記の養生シートの残存モノマー量はＨＳ−ＧＣ／ＭＳを用いて測定した。
測定は以下の条件で行った。
活性炭含有粘着シートを剥離した養生テープを２．５ｃｍ×５．０ｃｍにカットし、２０ｍｌバイアル瓶に入れ測定用サンプルとした。
(Measuring method)
The amount of residual monomer in the above curing sheet was measured using HS-GC / MS.
The measurement was performed under the following conditions.
The curing tape from which the activated carbon-containing adhesive sheet was peeled off was cut into 2.5 cm × 5.0 cm pieces and placed in a 20 ml vial to prepare a sample for measurement.
＜装置条件＞
（１）Ｈｅａｄｓｐａｃｅ Ｓａｍｐｌｅｒ（ヘッドスペースサンプラー）
装置名：Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｉｅｓ社製 Ｇ１８８８
オーブン温度；１００℃
ループ温度；１１０℃
トランスファーライン温度；１２０℃
ＧＣサイクル時間；４０分
バイアル平均化時間；３０分
バイアル加圧時間；４分
ループ注入時間；０．２０分
ループ平衡化時間；０．２０分
サンプル注入時間；１．００分
（２）ＧＣ（ガスクロマトグラフィー）：
装置名：Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｉｅｓ社製 ７８９０Ｂ ＧＣｓｙｓｔｅｍ
カラム；Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｉｅｓ社製 ＤＢ−ＷＡＸ（３０ｍ×２５０μｍφ×０．５μｍ）
キャリアーガス；Ｈｅ（ヘリウム）
カラム流量；１．０ｍｌ／ｍｉｎ
圧力；６．７ｐｓｉ（４０℃時）
カラム温度；初期４０℃（ホールド５ ｍｉｎ）→１０℃／１ ｍｉｎ（昇温）→２２０℃（ホールド１０ ｍｉｎ）
スプリット比；３０：１
注入口温度；２２０℃
（３）ＭＳ（ＭａｓｓＳｅｌｅｃｔｉｖｅ Ｄｅｔｅｃｔｏｒ ）
装置名：Ａｇｉｌｅｎｔ Ｔｅｃｈｎｏｌｏｇｉｅｓ社製 ５９７７Ｂ Ｉｎｅｒｔｐｌｕｓ
トランスファーライン温度；２２０℃
Ｓｃａｎモード
<Device conditions>
(1) Headspace Sampler (Headspace Sampler)
Device name: Agilent Technologies G1888
Oven temperature; 100 ° C
Loop temperature; 110 ° C
Transfer line temperature; 120 ° C
GC cycle time; 40 minutes vial averaging time; 30 minutes vial pressurization time; 4 minutes loop injection time; 0.20 minutes loop equilibration time; 0.20 minutes sample injection time; 1.00 minutes (2) GC ( Gas chromatography):
Device name: Agilent Technologies 7890B GCsystem
Column: DB-WAX manufactured by Agilent Technologies (30 m x 250 μm φ x 0.5 μm)
Carrier gas; He (helium)
Column flow rate; 1.0 ml / min
Pressure; 6.7 psi (at 40 ° C)
Column temperature: Initial 40 ° C (hold 5 min) → 10 ° C / 1 min (heat rise) → 220 ° C (hold 10 min)
Split ratio; 30: 1
Injection temperature: 220 ° C
(3) MS (Mass Selective Detector)
Device name: 5977B Intertplus manufactured by Agilent Technologies
Transfer line temperature; 220 ° C
Scan mode
＜評価基準＞
◎・・・検出限界以下
○・・・１ｐｐｍ未満
×・・・１ｐｐｍ以上
<Evaluation criteria>
◎ ・ ・ ・ Below the detection limit ○ ・ ・ ・ Less than 1ppm × ・ ・ ・ 1ppm or more
上記結果より、アクリル系樹脂（Ａ）に活性炭（Ｂ）を含有させてなる粘着剤組成物より形成される粘着剤である実施例では、粘着性能に優れるとともに、養生テープに対する脱臭効果にも優れるものであるのに対して、活性炭（Ｂ）を含有しない比較例では脱臭効果を有しないものである。 From the above results, in the example of the pressure-sensitive adhesive formed from the pressure-sensitive adhesive composition in which the acrylic resin (A) contains activated carbon (B), the adhesive performance is excellent and the deodorizing effect on the curing tape is also excellent. On the other hand, in the comparative example which does not contain activated carbon (B), it does not have a deodorizing effect.
本発明の粘着剤組成物を用いて得られる粘着剤は、良好な粘着性能を有するとともに部材（基材、被着体等）中の臭気成分や有害成分に対する吸着性能に優れたものとなり、種々の用途、たとえば建材用途（壁紙用や養生用）、表面保護用途、汚染除去用途、車載部材用途、航空機用途などに好適に用いることができる。 The pressure-sensitive adhesive obtained by using the pressure-sensitive adhesive composition of the present invention has good pressure-sensitive adhesive performance and is excellent in adsorption performance for odorous components and harmful components in members (base materials, adherends, etc.). For example, it can be suitably used for building materials (wallpaper and curing), surface protection, decontamination, in-vehicle members, aircraft, and the like.
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| DE112022002684T5 (en) | 2021-05-19 | 2024-03-21 | AGC Inc. | Vibration device and sound isolation device |
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