CN116867868A - Adhesive composition and adhesive tape - Google Patents
Adhesive composition and adhesive tape Download PDFInfo
- Publication number
- CN116867868A CN116867868A CN202280015421.4A CN202280015421A CN116867868A CN 116867868 A CN116867868 A CN 116867868A CN 202280015421 A CN202280015421 A CN 202280015421A CN 116867868 A CN116867868 A CN 116867868A
- Authority
- CN
- China
- Prior art keywords
- adhesive composition
- adhesive
- weight
- monomer
- acrylic copolymer
- 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
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 143
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 143
- 239000000203 mixture Substances 0.000 title claims abstract description 119
- 239000002390 adhesive tape Substances 0.000 title claims abstract description 47
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 69
- 239000002253 acid Substances 0.000 claims abstract description 42
- 239000012790 adhesive layer Substances 0.000 claims abstract description 41
- 238000003860 storage Methods 0.000 claims abstract description 24
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims description 90
- 239000011347 resin Substances 0.000 claims description 50
- 229920005989 resin Polymers 0.000 claims description 50
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000000524 functional group Chemical group 0.000 claims description 18
- 125000003368 amide group Chemical group 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 abstract description 20
- 239000002184 metal Substances 0.000 abstract description 20
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 47
- -1 acryl Chemical group 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 30
- 230000009477 glass transition Effects 0.000 description 25
- 238000000034 method Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 22
- 238000005259 measurement Methods 0.000 description 22
- 239000003431 cross linking reagent Substances 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 17
- 239000000758 substrate Substances 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 13
- 239000003505 polymerization initiator Substances 0.000 description 13
- 150000003505 terpenes Chemical class 0.000 description 13
- 235000007586 terpenes Nutrition 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 230000007797 corrosion Effects 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 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 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 150000002739 metals Chemical class 0.000 description 11
- 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 11
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 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 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 229920002799 BoPET Polymers 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000003918 potentiometric titration Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000012620 biological material Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- UFZHRTLJOSFQNY-UHFFFAOYSA-N dimethoxymethane 2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound COCOC.C(O)C(CC)(CO)CO UFZHRTLJOSFQNY-UHFFFAOYSA-N 0.000 description 3
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 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 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000004088 foaming agent Substances 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
- 238000010030 laminating Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 2
- 239000004631 polybutylene succinate Substances 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229960002703 undecylenic acid Drugs 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- VARVLWYFLHYARU-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;methyl prop-2-enoate Chemical compound COC(=O)C=C.CCC(CO)(CO)CO VARVLWYFLHYARU-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RTEZVHMDMFEURJ-UHFFFAOYSA-N 2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)C(C)(C)C RTEZVHMDMFEURJ-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
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- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NFWPZNNZUCPLAX-UHFFFAOYSA-N 4-methoxy-3-methylaniline Chemical compound COC1=CC=C(N)C=C1C NFWPZNNZUCPLAX-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 238000005336 cracking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000000752 ionisation method Methods 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
- 239000005001 laminate film Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920006118 nylon 56 Polymers 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
- 239000005011 phenolic resin Substances 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/24—Homopolymers or copolymers of amides or imides
- C09J133/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The invention provides an adhesive composition which is not easy to corrode metal and can exert excellent adhesive force. Further, an adhesive tape having an adhesive layer containing the adhesive composition is provided. The present invention relates to an adhesive composition comprising an acrylic copolymer containing 50% by weight or more of structural units derived from n-heptyl (meth) acrylate, the adhesive composition having an acid value of 22mgKOH/g or less and a shear storage modulus at 23 ℃ of 6X 10 4 Pa or more and 5×10 5 Pa or below.
Description
Technical Field
The present invention relates to an adhesive composition and an adhesive tape.
Background
Conventionally, in electronic parts, vehicles, houses and building materials, an adhesive tape having an adhesive layer containing an adhesive has been widely used for fixing the parts (for example, patent documents 1 to 3). Specifically, for example, an adhesive tape is used to adhere a cover panel for protecting the surface of a portable electronic device to a touch panel module or a display panel module or to adhere the touch panel module to the display panel module.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2015-052050
Patent document 2: japanese patent application laid-open No. 2015-021067
Patent document 3: japanese patent application laid-open No. 2015-120876
Disclosure of Invention
Problems to be solved by the application
Conventionally, in electronic equipment parts, in-vehicle parts, and the like, metals have been generally used in parts such as sensors and copper wiring. When the adhesive composition is used around the metal, the metal may corrode, and the metal may be degraded over time.
The purpose of the present application is to provide an adhesive composition which is less likely to corrode metals and which can exhibit excellent adhesion. The present application also provides an adhesive tape having an adhesive layer containing the adhesive composition.
Means for solving the problems
The application 1 relates to an adhesive composition comprising an acrylic copolymer,
the acrylic copolymer contains 50% by weight or more of structural units derived from n-heptyl (meth) acrylate, the acid value of the adhesive composition is 22mgKOH/g or less, and the shear storage modulus at 23 ℃ is 6X 10 4 Pa or more and 5×10 5 Pa or below.
The application 2 is an adhesive composition according to the application 1, wherein,
The acid value of the acrylic copolymer is 22mgKOH/g or less.
Invention 3 is an adhesive composition according to the application 1 or 2, wherein,
the acrylic copolymer further contains a structural unit derived from a monomer having a polar functional group, and the monomer having a polar functional group contains a monomer having an amide group.
Invention 4 is an adhesive composition according to application 3, wherein,
the content of the structural unit derived from the amide group-containing monomer in the acrylic copolymer is 2 to 30% by weight.
Invention 5 is an adhesive composition according to the application 3 or 4, wherein,
the monomer having a polar functional group further contains a monomer having a hydroxyl group.
Invention 6 is an adhesive composition according to application 5, wherein,
the content of the structural unit derived from the monomer having a hydroxyl group in the acrylic copolymer is 0.01% by weight or more and 5% by weight or less.
The application 7 is the adhesive composition according to the application 1, 2, 3, 4, 5 or 6, further comprising a tackifying resin having an acid value of 10mgKOH/g or less.
The application 8 is an adhesive composition according to the application 7, wherein,
The hydroxyl value of the tackifying resin is 50mgKOH/g or less.
The application 9 is an adhesive composition according to the application 1, 2, 3, 4, 5, 6, 7 or 8, wherein,
the content of carbon derived from living beings is 30% by weight or more.
The application 10 relates to an adhesive tape having an adhesive layer containing the adhesive composition of the application 1, 2, 3, 4, 5, 6, 7, 8 or 9.
The present application 11 is an adhesive tape according to the present application 10, wherein,
the gel fraction of the adhesive layer is 20 to 50 wt%.
The application 12 is an adhesive tape according to the application 10, wherein,
the gel fraction of the adhesive layer is 60 to 95 wt%.
In the present specification, (meth) acrylate means acrylate or methacrylate, and (meth) acrylic acid means acrylic acid or methacrylic acid. The acrylic copolymer may be a methacrylic copolymer.
The present application will be described in detail below.
The present inventors have studied the case of using an acrylic monomer containing bio-derived carbon as an acrylic monomer constituting an acrylic copolymer in an adhesive composition containing the acrylic copolymer. Among them, the use of n-heptyl (meth) acrylate (having the number of carbon atoms of the acryl group=7) in a specific amount or more can be expected to exert excellent adhesive force.
However, the present inventors have also found that: regarding n-heptyl (meth) acrylate, the glass transition temperature obtained from the tan δ of the homopolymer reaching a maximum temperature is lower than expected, and the cohesive force of the adhesive composition is lower than expected. Namely, it can be seen that: in contrast to predictions based on glass transition temperature trends obtained by Differential Scanning Calorimetry (DSC), for example, n-heptyl acrylate has a lower glass transition temperature at which tan δ of a homopolymer reaches a maximum temperature than butyl acrylate and 2-ethylhexyl acrylate (carbon number of acryl=4 and 8).
Here, in order to use n-heptyl (meth) acrylate and to improve the cohesive force of the adhesive composition and to exert excellent adhesive force, it is considered that, for example, acrylic acid is copolymerized in a large amount.
However, when an adhesive composition containing an acrylic copolymer obtained by copolymerizing a large amount of acrylic acid is used around a metal, there is a problem in that the metal corrodes and defects occur with the passage of time. In contrast, the present inventors have found that by adjusting the acid value of the adhesive composition to a certain value or less and the shear storage modulus at 23 ℃ to a specific range, an adhesive composition capable of reducing corrosion of metals and exhibiting excellent adhesive force can be obtained, and completed the present invention.
The adhesive composition of the present invention contains an acrylic copolymer.
The above-mentioned acrylic copolymer contains a structural unit derived from n-heptyl (meth) acrylate. Thus, the adhesive composition of the present invention can exhibit excellent adhesive force.
Preferably, the above-mentioned acrylic copolymer contains a structural unit derived from n-heptyl (meth) acrylate containing bio-derived carbon. The inclusion of structural units derived from n-heptyl (meth) acrylate in the acrylic copolymer can increase the content of bio-derived carbon in the entire adhesive composition by including the bio-derived carbon in the n-heptyl (meth) acrylate. By using a biological material instead of a petroleum-derived material, petroleum resources can be saved, and the use of the biological material is a countermeasure against exhaustion of petroleum resources and carbon dioxide emissions caused by combustion of petroleum-derived products.
The bio-derived carbon-containing n-heptyl (meth) acrylate is not particularly limited as long as it contains bio-derived carbon, and is preferably synthesized by esterification of n-heptanol, which is a bio-derived material, with (meth) acrylic acid. It is also preferable that n-heptanol be synthesized by transesterification with (meth) acrylic acid ester as a biological material.
The n-heptanol, which is a biological material, can be easily obtained at low cost by cracking a material collected from animals, plants, and the like (for example, ricinoleic acid derived from castor oil, and the like) as a raw material.
In the acrylic copolymer, the lower limit of the content of the structural unit derived from n-heptyl (meth) acrylate is 50% by weight. When the content of the structural unit is 50% by weight or more, the adhesive strength of the adhesive composition becomes high. In addition, when the content of the structural unit of n-heptyl (meth) acrylate containing bio-derived carbon is 50 wt% or more, the content of bio-derived carbon in the whole adhesive composition can be increased.
The content of the structural unit derived from n-heptyl (meth) acrylate is not particularly limited, but is preferably more than 50% by weight, more preferably 60% by weight, and still more preferably 70% by weight.
The upper limit of the content of the structural unit derived from n-heptyl (meth) acrylate is not particularly limited, but is preferably 99% by weight, and more preferably 97% by weight, from the viewpoint of adjusting the shear storage modulus at 23 ℃ of the adhesive composition to a range described later.
The content of the structural unit derived from n-heptyl (meth) acrylate in the acrylic copolymer can be determined by mass analysis of the acrylic copolymer 1 H-NMR measurement was performed and the integrated intensity ratio of the peak derived from the hydrogen of n-heptyl (meth) acrylate was calculated.
Preferably, the acrylic copolymer further contains a structural unit derived from a monomer having a polar functional group.
By incorporating the structural unit derived from the monomer having a polar functional group in the acrylic copolymer, the cohesive force of the adhesive composition is improved, and the shear storage modulus at 23 ℃ easily satisfies the range described later, thereby further improving the adhesive force.
The monomer having a polar functional group is not particularly limited, and examples thereof include: a monomer having a hydroxyl group, a monomer having a carboxyl group, a monomer having an ether group, a monomer having a glycidyl group, a monomer having an amide group, a monomer having a nitrile group, and the like. These monomers having polar functional groups may be used alone or in combination of 2 or more. Among them, monomers having a hydroxyl group, monomers having a carboxyl group, and monomers having an amide group are preferable in that the shear storage modulus at 23 ℃ of the adhesive composition more easily satisfies the range described below. In addition to the shear storage modulus at 23 ℃ of the adhesive composition, the acid value is also easily in the range described below, and from the viewpoint of further reducing corrosion of metals and further improving adhesion, monomers having hydroxyl groups and monomers having amide groups are more preferable. From the viewpoint of sufficiently suppressing the acid value of the adhesive composition and further reducing corrosion of metals, it is further preferable not to use a monomer having a carboxyl group.
Examples of the monomer having a hydroxyl group include: acrylic monomers having a hydroxyl group such as 4-hydroxybutyl (meth) acrylate and 2-hydroxyethyl (meth) acrylate.
Examples of the monomer having a carboxyl group include: acrylic monomers having a carboxyl group such as (meth) acrylic acid.
Examples of the monomer having a glycidyl group include: acrylic monomers having a glycidyl group such as glycidyl (meth) acrylate.
Examples of the monomer having an amide group include: an acrylic monomer having an amide group such as (meth) acrylamide, dimethyl (meth) acrylamide, diethyl (meth) acrylamide, isopropyl (meth) acrylamide, t-butyl (meth) acrylamide, methoxymethyl (meth) acrylamide, butoxymethyl (meth) acrylamide, and the like. Among them, from the viewpoints of easy acquisition and easy handling, (meth) acrylamide, dimethyl (meth) acrylamide and diethyl (meth) acrylamide are preferable.
Examples of the monomer having a nitrile group include: acrylic monomers having a nitrile group such as (meth) acrylonitrile.
The content of the structural unit derived from the monomer having a polar functional group in the acrylic copolymer is not particularly limited, and may be determined according to the type of the monomer having a polar functional group.
When the monomer having a polar functional group contains the monomer having a hydroxyl group, the content of the structural unit derived from the monomer having a hydroxyl group in the acrylic copolymer is not particularly limited, but the lower limit is preferably 0.01% by weight, and the upper limit is preferably 5% by weight. When the content of the structural unit is within the above range, the shear storage modulus at 23℃of the adhesive composition more easily satisfies the range described later, and the adhesive force is further improved. The lower limit of the above structural unit is more preferably 0.05% by weight, and the upper limit is more preferably 1% by weight.
When the polar functional group-containing monomer contains the amide group-containing monomer, the content of the structural unit derived from the amide group-containing monomer in the acrylic copolymer is not particularly limited, but the lower limit is preferably 2% by weight, and the upper limit is preferably 30% by weight. When the content of the structural unit is within the above range, the shear storage modulus at 23℃of the adhesive composition more easily satisfies the range described later, and the adhesive force is further improved. The lower limit of the above structural unit is more preferably 5% by weight, the upper limit is more preferably 25% by weight, the lower limit is more preferably 10% by weight, and the upper limit is more preferably 20% by weight.
The content of the structural unit derived from the monomer having a polar functional group in the acrylic copolymer can be determined by mass analysis of the acrylic copolymer 1 H-NMR measurement was performed and the ratio of the integrated intensities of the peaks of hydrogen from the respective monomers was calculated.
The acrylic copolymer may have a structural unit derived from a monomer having a glass transition temperature (Tg) of-35 ℃ or higher. The adhesive force of the adhesive layer obtained by the acrylic copolymer having a structural unit derived from a monomer having a glass transition temperature (Tg) of-35 ℃ or higher is further improved. The monomer having a glass transition temperature (Tg) of-35℃or higher means a monomer having a glass transition temperature (Tg) of-35℃or higher when a homopolymer is produced, and the glass transition temperature (Tg) of the homopolymer can be obtained by, for example, differential scanning calorimetric measurement.
The glass transition temperature (Tg) of the monomer having a glass transition temperature (Tg) of-35 ℃ or higher is more preferably-15 ℃ or higher. The upper limit of the glass transition temperature (Tg) is not particularly limited, but is preferably 180 ℃, more preferably 150 ℃.
The monomer having a glass transition temperature (Tg) of-35℃or higher is not particularly limited, but a monomer having no crosslinkable functional group is preferable, and specific examples thereof include: methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, isobornyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, trimethylolpropane methylacrylate (Japanese) is a prosthetic. Among them, isobornyl (meth) acrylate and tetrahydrofurfuryl (meth) acrylate are preferable.
The content of the structural unit derived from the monomer having a glass transition temperature (Tg) of-35 ℃ or higher in the acrylic copolymer is not particularly limited, but is preferably 5% by weight or more and 70% by weight or less. When the content of the structural unit derived from the monomer having a glass transition temperature (Tg) of-35 ℃ or higher is 70 wt% or less, the following property to the irregularities of the obtained pressure-sensitive adhesive layer is further improved. The more preferable upper limit of the content of the structural unit derived from the monomer having a glass transition temperature (Tg) of-35 ℃ or higher is 65 wt%, the more preferable upper limit is 60 wt%, the more preferable upper limit is 55 wt%, and the particularly preferable upper limit is 50 wt%. The more preferable lower limit of the content of the structural unit derived from the monomer having a glass transition temperature (Tg) of-35℃or higher is 10% by weight.
The content of the structural unit derived from the monomer having a glass transition temperature (Tg) of-35℃or higher in the acrylic copolymer can be determined by mass analysis of the acrylic copolymer 1 H-NMR measurement was performed and the ratio of the integrated intensities of the peaks of hydrogen from the respective monomers was calculated.
The acrylic copolymer preferably has a structural unit derived from a monomer having a ring structure. By providing the acrylic copolymer with a structural unit derived from a monomer having a ring structure, an adhesive tape can be suitably used as an optical adhesive tape.
The ring structure is not particularly limited, and examples thereof include: alicyclic structure, aromatic ring structure, heterocyclic structure, and the like. Examples of the monomer having a ring structure include: isobornyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, trimethylolpropane methylal (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, and the like. Among them, isobornyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, trimethylolpropane methylal (meth) acrylate are preferable. Among them, a monomer derived from a living organism is particularly preferable, and isobornyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, and trimethylolpropane methylal (meth) acrylate are more preferable.
The acrylic copolymer may have a structural unit derived from a monomer other than the structural unit derived from n-heptyl (meth) acrylate, the structural unit derived from the monomer having a polar functional group, and the structural unit derived from a monomer having a glass transition temperature (Tg) of-35 ℃ or higher.
The other monomer is not particularly limited, and examples thereof include: alkyl (meth) acrylates.
Examples of the alkyl (meth) acrylate include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, myristyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, esters of 5, 7-trimethyl-2- (1, 3-trimethylbutyl) octanol-1 with (meth) acrylic acid, esters of an alcohol having a total of 18 carbon atoms of 1 or 2 methyl groups in a linear main chain with (meth) acrylic acid, behenyl (meth) acrylate, eicosyl (meth) acrylate, and the like. These alkyl (meth) acrylates may be used alone or in combination of 2 or more.
Examples of the other monomer include cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, and polypropylene glycol mono (meth) acrylate, and isobornyl (meth) acrylate is preferable from the viewpoint of excellent rebound resistance. Further, as the other monomer, for example, various monomers used for general acrylic polymers such as vinyl carboxylate, e.g., vinyl acetate, and styrene may be used. These other monomers may be used alone or in combination of 2 or more.
The content of the structural unit derived from the other monomer in the acrylic copolymer can be determined by mass analysis of the acrylic copolymer 1 H-NMR measurement was performed and the ratio of the integrated intensities of the peaks of hydrogen from the respective monomers was calculated.
The monomer having a polar functional group and the other monomer preferably contain bio-derived carbon, but may contain only petroleum-derived materials without bio-derived carbon. In theory, all of the acrylic monomers constituting the acrylic copolymer may be monomers containing bio-derived carbon. From the viewpoints of cost and productivity of the adhesive composition, a monomer containing bio-derived carbon which is inexpensive and easily available can be used, and a monomer containing only petroleum-derived materials can be used in combination thereof.
The acid value of the acrylic copolymer is not particularly limited, but the preferable upper limit is 22mgKOH/g. When the acid value of the acrylic copolymer is 22mgKOH/g or less, the acid value of the adhesive composition easily satisfies the range described later, and corrosion of metals can be further reduced. The more preferable upper limit of the acid value of the acrylic copolymer is 10mgKOH/g. The lower limit of the acid value of the acrylic copolymer is not particularly limited, and may be 0mgKOH/g.
The acid value of the acrylic copolymer can be determined by the same method as that of the adhesive composition, for example. Specifically, the acid value of the acrylic copolymer of the present invention is the mg of potassium hydroxide required for neutralizing the acid contained in sample 1g, and can be determined by the potentiometric titration method according to JIS K0070, for example.
The glass transition temperature (Tg) of the acrylic copolymer is not particularly limited, but is preferably-20℃or lower. When the glass transition temperature (Tg) of the acrylic copolymer is-20 ℃ or lower, the adhesive composition exhibits improved following properties with respect to an adherend, and further exhibits improved adhesive force. The glass transition temperature (Tg) of the acrylic copolymer is more preferably-30℃or lower, still more preferably-40℃or lower, and still more preferably-50℃or lower. The lower limit of the glass transition temperature (Tg) of the acrylic copolymer is not particularly limited, but is usually-90℃or higher, preferably-80℃or higher.
The glass transition temperature (Tg) of the acrylic copolymer can be determined by, for example, differential scanning calorimetry.
The weight average molecular weight (Mw) of the acrylic copolymer is not particularly limited, but is preferably 20 tens of thousands, and is preferably 200 tens of thousands. When the weight average molecular weight of the acrylic copolymer is within the above range, the adhesive force of the adhesive composition is further improved. The preferable lower limit of the weight average molecular weight of the acrylic copolymer is 40 ten thousand, the preferable upper limit is 180 ten thousand, the preferable lower limit is 50 ten thousand, and the preferable upper limit is 150 ten thousand.
The weight average molecular weight (Mw) is a weight average molecular weight in terms of standard polystyrene measured by GPC (Gel Permeation Chromatography: gel permeation chromatography). Specifically, the acrylic copolymer was diluted 50 times with Tetrahydrofuran (THF), and the resulting diluted solution was filtered through a filter (material: polytetrafluoroethylene, pore size: 0.2 μm) to prepare a measurement sample. The measurement sample was then supplied to a gel permeation chromatograph (trade name "2690Separations Module" manufactured by Waters corporation or equivalent thereof), and GPC measurement was performed under conditions of a sample flow rate of 1 ml/min and a column temperature of 40 ℃. The polystyrene-equivalent molecular weight of the acrylic copolymer was measured, and this value was defined as the weight average molecular weight of the acrylic copolymer.
The acrylic copolymer can be obtained by radical reaction of a monomer mixture as a raw material in the presence of a polymerization initiator.
The mode of radical reaction is not particularly limited, and examples thereof include: living radical polymerization, and the like. According to living radical polymerization, a copolymer having a more uniform molecular weight and composition can be obtained as compared with radical polymerization, and the generation of low molecular weight components and the like is suppressed, and therefore, the cohesive force of the adhesive composition is improved and the adhesive force is further improved.
The polymerization method is not particularly limited, and conventionally known methods can be used. Examples of the polymerization method include: solution polymerization (boiling point polymerization or constant temperature polymerization), UV polymerization, emulsion polymerization, suspension polymerization, bulk polymerization, and the like. Among them, solution polymerization and UV polymerization are preferable from the viewpoint that the adhesive force of the adhesive composition becomes higher. Further, from the viewpoint of easily mixing the obtained acrylic copolymer with the tackifying resin, the adhesive force of the adhesive composition can be further improved, and the solution polymerization is more preferable.
In the case of using solution polymerization as a polymerization method, examples of the reaction solvent include: ethyl acetate, toluene, methyl ethyl ketone, dimethyl sulfoxide, ethanol, acetone, diethyl ether, and the like. These reaction solvents may be used alone or in combination of 2 or more.
The polymerization initiator is not particularly limited, and examples thereof include: organic peroxides, azo compounds, and the like. Examples of the organic peroxide include: 1, 1-bis (t-hexylperoxy) -3, 5-trimethylcyclohexane, t-hexyl peroxypivalate, t-butyl peroxypivalate, 2, 5-dimethyl-2, 5-bis (2-ethylhexanoylperoxy) hexane, t-hexyl peroxy2-ethylhexanoate, t-butyl peroxyisobutyrate, t-butyl peroxy3, 5-trimethylhexanoate, t-butyl peroxylaurate, and the like. Examples of the azo compound include: azobisisobutyronitrile, azobicyclohexane carbonitrile, and the like. These polymerization initiators may be used alone or in combination of 2 or more.
In the case of living radical polymerization, examples of the polymerization initiator include: an organic tellurium polymerization initiator. The organic tellurium polymerization initiator is not particularly limited as long as it is an organic tellurium polymerization initiator generally used in living radical polymerization, and examples thereof include: an organic tellurium compound, an organic telluride compound, and the like. In living radical polymerization, an azo compound may be used as the polymerization initiator for the purpose of promoting the polymerization rate, in addition to the organic tellurium polymerization initiator.
Preferably, the adhesive composition does not contain a surfactant.
The adhesive composition does not contain a surfactant, so that the adhesive force of the adhesive tape, particularly the adhesive force at high temperature, is further improved. The fact that the adhesive composition does not contain a surfactant means that the content of the surfactant in the adhesive composition is 3% by weight or less, preferably 1% by weight or less.
In order to make the adhesive composition free of surfactant, it is preferable that the surfactant is not used in obtaining the acrylic copolymer. For this purpose, for example, as a polymerization method for obtaining the acrylic copolymer, solution polymerization, UV polymerization, or the like may be used.
The content of the surfactant can be determined, for example, by measuring the adhesive composition using a liquid chromatography mass spectrometer (for example, NEXCORA, manufactured by Shimadzu corporation, and exact, manufactured by Thermo Fisher Scientific corporation). More specifically, the ethyl acetate solution of the adhesive composition was filtered through a filter (material: polytetrafluoroethylene, pore size: 0.2 μm). About 10. Mu.L of the obtained filtrate was injected into a liquid chromatograph mass spectrometer and analyzed under the following conditions. The content of the surfactant can be determined from the area ratio of the peak corresponding to the surfactant in the adhesive composition. It is preferable that a calibration curve indicating the relationship between the surfactant content and the peak area ratio is prepared for each surfactant type by preparing a sample having a known surfactant content in the adhesive composition, and then analyzing the sample.
Column Thermo Fisher Scientific, hypersil GOLD (2.1×150mm)
Mobile phase acetonitrile
Column temperature 40 DEG C
Flow rate 1.0mL/min
Ionization method ESI
Capillary temperature of 350 DEG C
From the viewpoint of adjusting the shear storage modulus at 23 ℃, the adhesive composition of the present invention preferably further contains a crosslinking agent.
The crosslinking agent is not particularly limited, and examples thereof include: isocyanate-based crosslinking agents, aziridine-based crosslinking agents, epoxy-based crosslinking agents, metal chelate-based crosslinking agents, and the like. Among them, the isocyanate-based crosslinking agent is preferable in view of excellent adhesion between the adhesive composition and the adherend.
The molecular weight of the crosslinking agent is not particularly limited, and from the viewpoint of production, the molecular weight is preferably less than 2000, and preferably 100 or more.
The content of the crosslinking agent in the adhesive composition of the present invention is not particularly limited, but is preferably 0.05 parts by weight, and is preferably 7 parts by weight, based on 100 parts by weight of the acrylic copolymer. When the content of the crosslinking agent is within the above range, the shear storage modulus at 23℃of the adhesive composition more easily satisfies the range described later, and the adhesive force is further improved. The lower limit of the content of the crosslinking agent is more preferably 0.1 parts by weight, and the upper limit is more preferably 5 parts by weight.
The content of the crosslinking agent means the amount of the solid component of the crosslinking agent.
The adhesive composition of the present invention may further contain: and a crosslinking catalyst for promoting crosslinking by the crosslinking agent.
The crosslinking catalyst is not particularly limited, and examples of the crosslinking catalyst of the isocyanate-based crosslinking agent include dibutyltin dilaurate, dibutyltin diacetate, dioctyltin dilaurate, and the like.
The content of the crosslinking catalyst in the adhesive composition of the present invention is not particularly limited, but is preferably limited to 0.001 part by weight, preferably 3 parts by weight, more preferably 0.01 part by weight, and even more preferably 1 part by weight based on 100 parts by weight of the acrylic copolymer.
Preferably, the adhesive composition of the present invention further comprises a tackifying resin. Thereby, the adhesive force of the adhesive composition is further improved.
The acid value of the tackifying resin is not particularly limited, but the preferable upper limit is 10mgKOH/g. When the acid value of the tackifier resin is 10mgKOH/g or less, the acid value of the adhesive composition easily satisfies the range described later, and corrosion of metals can be further reduced. The more preferable upper limit of the acid value of the tackifying resin is 5mgKOH/g. The lower limit of the acid value of the tackifying resin is not particularly limited and may be 0mgKOH/g.
The acid value of the tackifying resin can be determined, for example, by the same method as the acid value of the adhesive composition. Specifically, the acid value of the tackifying resin of the present invention is the mg of potassium hydroxide required to neutralize the acid contained in sample 1g, and can be determined by a potentiometric titration method according to JIS K0070, for example.
The hydroxyl value of the tackifying resin is not particularly limited, but the preferable upper limit is 50mgKOH/g. When the hydroxyl value of the tackifying resin is 50mgKOH/g or less, the adhesive composition can be prevented from excessively absorbing moisture in the air, and therefore, corrosion of metals can be further reduced. The more preferable upper limit of the hydroxyl value of the tackifying resin is 40mgKOH/g. The lower limit of the hydroxyl value of the tackifying resin is not particularly limited, but is preferably 10mgKOH/g.
The hydroxyl value of the tackifying resin is the mg of potassium hydroxide required to neutralize the hydroxyl-bonded acetic acid when 1g of the sample is acetylated, and can be determined by neutralization titration according to JIS K0070, for example.
Specific examples of the tackifying resin include: rosin ester type tackifying resins, terpene type tackifying resins, coumarone-indene type tackifying resins, alicyclic saturated hydrocarbon type tackifying resins, C5 type petroleum tackifying resins, C9 type petroleum tackifying resins, C5-C9 copolymerization type petroleum tackifying resins, and the like. These tackifying resins may be used alone or in combination of 2 or more. Among them, at least 1 selected from rosin ester-based tackifying resins and terpene-based tackifying resins is preferable in that the acid value and the hydroxyl value easily satisfy the above ranges.
Examples of the rosin ester-based tackifying resin include: polymerized rosin ester resin, hydrogenated rosin ester resin, and the like. Examples of the terpene-based tackifying resin include: terpene resins, terpene phenol resins, and the like.
Preferably, the rosin ester-based tackifying resin and the terpene-based tackifying resin are bio-derived. Examples of the bio-derived rosin ester based tackifying resin include: rosin ester tackifying resins derived from natural resins such as rosin. Examples of the terpene-based tackifying resin derived from living things include: terpene tackifying resins such as essential oils derived from plants.
The content of the tackifying resin in the adhesive composition of the present invention is not particularly limited, but is preferably 10 parts by weight at a lower limit and 60 parts by weight at an upper limit, based on 100 parts by weight of the acrylic copolymer. When the content of the tackifying resin is within the above range, the adhesive force of the adhesive composition is further improved. The content of the tackifying resin is more preferably limited to 15 parts by weight, more preferably limited to 50 parts by weight, and still more preferably limited to 35 parts by weight.
In the case where the adhesive composition of the present invention is used for an optical adhesive tape, the content of the tackifying resin in the adhesive composition of the present invention is not particularly limited, but is preferably 0 parts by weight at the lower limit and 40 parts by weight at the upper limit, based on 100 parts by weight of the acrylic copolymer. When the content of the tackifier resin is within the above range, the adhesive tape can be suitably used as an optical adhesive tape. The more preferable upper limit of the content of the tackifying resin is 30 parts by weight.
The adhesive composition of the present invention may contain additives such as silane coupling agents, plasticizers, softeners, fillers, pigments, dyes, and the like, as needed.
The upper limit of the acid value of the adhesive composition of the present invention is 22mgKOH/g. Thus, the adhesive composition of the present invention becomes less susceptible to corrosion of metals. The more preferable upper limit of the acid value of the adhesive composition of the present invention is 10mgKOH/g. The lower limit of the acid value of the adhesive composition of the present invention is not particularly limited, and may be 0mgKOH/g.
The acid value of the adhesive composition of the present invention is the mg of potassium hydroxide required for neutralizing the acid contained in 1g of the sample, and can be determined by a potentiometric titration method according to JIS K0070, for example.
The method for adjusting the acid value of the adhesive composition of the present invention to the above range is not particularly limited, and the method for adjusting the composition and acid value of the acrylic copolymer, the type of the tackifying resin, and the acid value is preferable as described above.
The lower limit of the shear storage modulus at 23℃of the adhesive composition of the invention is 6X 10 4 Pa, an upper limit of 5X 10 5 Pa。
When the shear storage modulus at 23 ℃ is within the above range, the adhesive composition can exhibit excellent adhesive force, and the adhesion to an adherend is also improved. The lower limit of the shear storage modulus at 23℃is preferably 7X 10 4 Pa, a preferred upper limit is 4X 10 5 Pa, a more preferable lower limit is 8X 10 4 Pa, a more preferable upper limit is 3X 10 5 Pa。
The shear storage modulus at 23℃of the adhesive composition of the present invention can be determined, for example, by the following method. The adhesive composition of the present invention was applied to the release treated surface of the release treated PET film and dried so that the thickness of the dried adhesive layer became 100 μm. Alternatively, the adhesive layers are overlapped to form the adhesive layer so that the thickness becomes 100 μm. The adhesive layer thus obtained was subjected to measurement of a dynamic viscoelasticity spectrum at-50℃to 200℃under conditions of 5℃per minute and 10Hz in a shear mode using a viscoelasticity spectrometer (for example, manufactured by IT meter control Co., ltd., DVA-200).
The method for adjusting the shear storage modulus at 23℃of the adhesive composition of the present invention to the above range is not particularly limited, and the composition and weight average molecular weight of the acrylic copolymer and the type and amount of the crosslinking agent are preferably adjusted as described above.
The binder composition of the present invention preferably has a bio-derived carbon content of 10 wt% or more. The content of carbon derived from living beings of 10% by weight or more is a reference of "bio-based products".
When the content of the bio-derived carbon is 10 wt% or more, it is preferable from the viewpoint of saving petroleum resources and reducing the amount of carbon dioxide discharged. The lower limit of the content of the bio-derived carbon is more preferably 30% by weight or more, and the lower limit is more preferably 60% by weight. The upper limit of the content of the bio-derived carbon is not particularly limited and may be 100% by weight.
In contrast to this, radioisotope (C-14) was contained in a certain proportion in carbon derived from living beings, and C-14 was hardly contained in carbon derived from petroleum. Therefore, the content of the bio-derived carbon can be calculated by measuring the concentration of C-14 contained in the binder composition. Specifically, it can be measured according to ASTM D6866-20, a standard utilized in the relatively large number of bioplastic industries.
In addition, an adhesive tape having an adhesive layer containing the adhesive composition of the present invention is also one of the present invention.
The gel fraction of the pressure-sensitive adhesive layer is not particularly limited, but the lower limit is preferably 10% by weight, and the upper limit is preferably 70% by weight. When the gel fraction of the pressure-sensitive adhesive layer is within the above range, the pressure-sensitive adhesive force of the pressure-sensitive adhesive layer is further improved, and the adhesion to an adherend is also improved. The lower limit of the gel fraction of the adhesive layer is more preferably 20% by weight, and the upper limit is more preferably 50% by weight.
In the case of using the pressure-sensitive adhesive tape of the present invention as an optical pressure-sensitive adhesive tape, the gel fraction of the pressure-sensitive adhesive layer is not particularly limited, but the lower limit is preferably 60% by weight, and the upper limit is preferably 98% by weight. When the gel fraction of the pressure-sensitive adhesive layer is within the above range, the pressure-sensitive adhesive tape can be suitably used as an optical pressure-sensitive adhesive tape. The lower limit of the gel fraction of the adhesive layer is more preferably 70% by weight, and the upper limit is more preferably 95% by weight.
The gel fraction of the adhesive layer was measured as follows.
First, the adhesive tape was cut into a 20mm×40mm flat rectangular shape, and a test piece was prepared, immersed in ethyl acetate at 23 ℃ for 24 hours, taken out of ethyl acetate, and dried at 110 ℃ for 1 hour. The weight of the dried test piece was measured, and the gel fraction was calculated using the following formula (1). The release film for protecting the adhesive layer was not laminated on the test piece.
Gel fraction (wt%) =100× (W 2 -W 0 )/(W 1 -W 0 )(1)
(W 0 : weight of substrate, W 1 : weight of test piece before immersion, W 2 : weight of the impregnated and dried test piece
Preferably, the lower limit of the shear storage modulus at 23℃of the adhesive layer is 6X 10 4 Pa, an upper limit of 5X 10 5 Pa。
When the shear storage modulus at 23 ℃ is within the above range, the adhesive layer can exhibit excellent adhesive force, and the adhesion to an adherend is also improved. The lower limit of the shear storage modulus at 23℃is preferably 7X 10 4 Pa, a preferred upper limit is 4X 10 5 Pa, a more preferable lower limit is 8X 10 4 Pa, a more preferable upper limit is 3X 10 5 Pa。
The shear storage modulus at 23℃of the pressure-sensitive adhesive layer can be determined by the following method, for example. For the adhesive layer, a dynamic viscoelasticity spectrum was measured at-50℃to 200℃under conditions of 5℃per minute and 10Hz in a shear mode using a viscoelasticity spectrometer (for example, DVA-200, manufactured by IT meter control Co.). When the pressure-sensitive adhesive layer is smaller than 100 μm, the pressure-sensitive adhesive layer for measurement is formed so that the thickness becomes 100 μm or more by overlapping the pressure-sensitive adhesive layers. The obtained pressure-sensitive adhesive layer for measurement was subjected to measurement of a dynamic viscoelasticity spectrum at-50℃to 200℃under conditions of 5℃per minute and 10Hz in a shear mode using a viscoelasticity spectrometer (for example, DVA-200, manufactured by IT meter control Co.).
Regarding the adhesive tape of the present invention, according to JIS Z0237: the lower limit of 180 DEG peel force for SUS plate measured in 2009 is preferably 5N/25mm, and the lower limit is more preferably 7N/25mm. The upper limit of the 180 DEG peel force is not particularly limited, but is preferably about 25N/25mm as the upper limit is higher.
According to JIS Z0237 described above: the 180 ° peel force to SUS plate measured in 2009 was measured as follows. First, the adhesive tape was cut into test pieces having a width of 25mm×a length of 75 mm. After the test piece was placed on the SUS plate with the adhesive layer facing the SUS plate, a 2kg rubber roller was reciprocated on the test piece at a speed of 300mm/min, and bonding was performed. Then, the mixture was cured at 23℃and 50% humidity for 20 minutes to prepare a test specimen. According to JIS Z0237: 2009, the test specimen was peeled off in the 180℃direction at a stretching speed of 300mm/min under the conditions of 23℃and 50% humidity, and the adhesive force (N/25 mm) was measured.
In the case where the pressure-sensitive adhesive tape is a non-supporting tape having no base material or a double-sided pressure-sensitive adhesive tape having pressure-sensitive adhesive layers on both sides of a base material, the other pressure-sensitive adhesive layer (the side on which measurement is not performed) is laminated with a polyethylene terephthalate film (for example, manufactured by FUTAMURA CHEMICAL corporation, FE2002 or equivalent) having a thickness of 23 μm on the surface thereof, and then bonded to the SUS plate.
The thickness of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive tape of the present invention is not particularly limited, but is preferably 3 μm in lower limit and 300 μm in upper limit. When the thickness of the adhesive layer is within the above range, the adhesive force of the adhesive composition is further improved. The lower limit of the thickness of the pressure-sensitive adhesive layer is more preferably 5. Mu.m, and the lower limit thereof is more preferably 10. Mu.m. The thickness of the pressure-sensitive adhesive layer is more preferably 200 μm in upper limit, and still more preferably 100 μm in upper limit.
The pressure-sensitive adhesive tape of the present invention may be a non-supporting tape having no base material, a single-sided pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer on one side of a base material, or a double-sided pressure-sensitive adhesive tape having a pressure-sensitive adhesive layer on both sides of a base material. When the adhesive tape of the present invention is used as an optical adhesive tape, a non-supporting tape having no base material is preferable.
The substrate is not particularly limited, and conventionally known substrates can be used, and in order to increase the carbon content of the whole pressure-sensitive adhesive tape, a substrate derived from a living organism is preferably used.
Examples of the biological-derived substrate include: films and nonwoven fabrics comprising Polyesters (PES) such as polyethylene terephthalate (PET), polyethylene furandicarboxylate (PEF), polylactic acid (PLA), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), polybutylene succinate (PBS) and the like, which are derived from plants. In addition, there may be mentioned: films and nonwoven fabrics comprising Polyethylene (PE), polypropylene (PP), polyurethane (PU), triacetyl cellulose (TAC), cellulose, polyamide (PA) and the like derived from plants.
From the viewpoint of the strength of the substrate, the substrate is preferably a film containing PES or a film containing PA. Further, from the viewpoints of heat resistance and oil resistance, a film containing PA is preferable.
Examples of the PA-containing film include: nylon 11, nylon 1010, nylon 610, nylon 510, nylon 410, etc. using castor oil as a raw material, nylon 56, etc. using cellulose as a raw material.
In addition, from the viewpoint of reducing environmental load by reducing the amount of new petroleum resources used and suppressing carbon dioxide emissions, a substrate using renewable resources can be used. Examples of the method for regenerating the resource include: a method of recovering waste such as packaging containers, home appliances, automobiles, construction materials, foods, and the like, and waste generated in the production process, and reusing the extracted material as a raw material by washing, decontamination, or decomposition by heating or fermentation. Examples of the substrate using the renewable resources include: films and nonwoven fabrics containing PET, PBT, PE, PP, PA and the like, which are obtained by resying the recovered plastic, are used as raw materials. The waste recovered may be burned to be used as heat energy associated with the production of a base material or a raw material thereof, or the oil and fat contained in the waste recovered may be mixed with petroleum, and the mixture may be fractionated and purified to obtain a substance as a raw material.
The base material may be a foam base material from the viewpoint of improving compression characteristics.
The foam base material is preferably a foam base material containing PE, PP and/or PU, and more preferably a foam base material containing PE from the viewpoint of high flexibility and strength. Examples of the constituent of the foamed substrate containing PE include PE using sugar cane as a raw material.
The method for producing the foam base material is not particularly limited, and for example, the following methods are preferable: a foamable resin composition containing a PE resin containing PE produced from sugarcane and a foaming agent is prepared, and the foaming agent is foamed and, if necessary, the resultant polyolefin foam is crosslinked when the foamable resin composition is extruded into a sheet form by using an extruder.
The thickness of the foam base material is not particularly limited, but is preferably 50 μm in the lower limit and 5000 μm in the upper limit. When the thickness of the foam base material is within this range, high flexibility that enables adhesion along the shape of the adherend can be exhibited while exhibiting high impact resistance. The upper limit of the thickness of the foamed base material is more preferably 1000. Mu.m, and the upper limit thereof is still more preferably 300. Mu.m.
The adhesive tape of the present invention preferably has a lower limit of 3 μm and an upper limit of 6000 μm in total thickness (total of thicknesses of the substrate and the adhesive layer) of the adhesive tape. When the total thickness of the adhesive tape is within the above range, the adhesive force is further improved. The more preferable upper limit of the total thickness of the adhesive tape is 1200 μm, and the more preferable upper limit is 500 μm.
The haze of the pressure-sensitive adhesive tape of the present invention is not particularly limited, and in the case of using the pressure-sensitive adhesive tape of the present invention as an optical pressure-sensitive adhesive tape, the upper limit is preferably 1, and more preferably 0.6 or less. Haze of the adhesive tape was determined in accordance with JIS K7136: 2000.
The method for producing the adhesive tape of the present invention is not particularly limited, and the adhesive tape can be produced by a conventionally known production method. For example, in the case of a double-sided adhesive tape, the following method can be mentioned.
First, a solvent is added to an acrylic copolymer, a crosslinking agent, a tackifying resin, and the like, if necessary, to prepare a solution of an adhesive a, the solution of the adhesive a is applied to the surface of a substrate, and the solvent in the solution is completely dried and removed to form an adhesive layer a. Next, on the pressure-sensitive adhesive layer a formed, a release film was superimposed with its release treated surface facing the pressure-sensitive adhesive layer a.
Next, another release film other than the release film was prepared, a solution of the adhesive B prepared by the same procedure as described above was applied to the release treated surface of the release film, and the solvent in the solution was completely dried and removed, thereby preparing a laminated film having the adhesive layer B formed on the surface of the release film. A laminate was produced by laminating a laminate film, which was obtained by laminating the back surface of the base material on which the adhesive layer a was formed, with the adhesive layer B facing the back surface of the base material. Then, the laminate is pressed by a rubber roll or the like, whereby a double-sided adhesive tape having an adhesive layer on both sides of a substrate and having the surface of the adhesive layer covered with a release film can be obtained.
In addition, 2 sets of laminated films were produced in the same manner, and these laminated films were stacked on each of the two surfaces of the base material in a state in which the adhesive layers of the laminated films were opposed to the base material, to produce a laminated body, and the laminated body was pressed by a rubber roll or the like, whereby a double-sided adhesive tape having adhesive layers on the two surfaces of the base material and the surfaces of the adhesive layers were covered with a release film was obtained.
The use of the pressure-sensitive adhesive tape of the present invention is not particularly limited, and is preferably used for fixing electronic equipment parts or vehicle-mounted parts because corrosion of metal can be reduced and excellent adhesive force can be exerted. Specifically, the adhesive tape of the present invention can be suitably used for adhesive fixation of electronic device components in a large-sized portable electronic device, adhesive fixation of in-vehicle components (for example, in-vehicle panels), and the like.
Effects of the invention
According to the present invention, an adhesive composition which is less likely to corrode metals and which can exhibit excellent adhesion can be provided. In addition, according to the present invention, an adhesive tape having an adhesive layer containing the adhesive composition can be provided.
Detailed Description
The following describes the mode of the present invention in more detail by referring to examples, but the present invention is not limited to the examples.
< n-heptyl acrylate containing bio-derived carbon >
Ricinoleic acid derived from castor oil is cracked to give a mixture comprising undecylenic acid and heptanol. Next, n-heptanol containing bio-derived carbon is obtained by separating undecylenic acid by distillation. N-heptanol containing bio-derived carbon is esterified with acrylic acid (manufactured by japan catalyst corporation) to prepare n-heptanoate.
< other acrylic monomer >
Acrylamide (Tokyo chemical Co., ltd.)
Dimethylacrylamide (manufactured by Tokyo chemical industry Co., ltd.)
Diethyl acrylamide (manufactured by Tokyo chemical industry Co., ltd.)
Isobornyl acrylate (manufactured by osaka organic chemical industry Co., ltd.)
Acrylic acid (manufactured by Japanese catalyst Co., ltd.)
2-hydroxyethyl acrylate (manufactured by Osaka organic chemical industry Co., ltd.)
< crosslinker >
Isocyanate-based crosslinking agent (CORONATE L-45, manufactured by Tosoh Co., ltd.)
< tackifying resin >)
Rosin ester (rosin ester D-135, acid value 13mgKOH/g, hydroxyl value 45mgKOH/g, manufactured by Deskaching chemical Co., ltd.)
Terpene phenol A (terpene phenol G-150, acid value 0mgKOH/G, hydroxyl value 135mgKOH/G, YASUHARA CHEMICAL CO., LTD.)
Terpene phenol B (terpene phenol UH-115, acid value 0mgKOH/g, hydroxyl value 25mgKOH/g, YASUHARA CHEMICAL CO., LTD.)
Example 1
(1) Production of acrylic copolymer
Ethyl acetate as a polymerization solvent was added to the reaction vessel, bubbling was performed with nitrogen gas, and then the reaction vessel was heated while flowing nitrogen gas, and reflux was started. Next, 0.1 part by weight of azobisisobutyronitrile as a polymerization initiator was diluted 10 times with ethyl acetate, and the resulting polymerization initiator solution was charged into a reaction vessel, and 98.9 parts by weight of n-heptyl acrylate, 1 part by weight of acrylic acid, and 0.1 part by weight of 2-hydroxyethyl acrylate were added dropwise over 2 hours. After completion of the dropwise addition, 0.1 part by weight of azobisisobutyronitrile as a polymerization initiator was diluted 10 times with ethyl acetate to obtain a polymerization initiator solution, which was again put into a reaction vessel to perform a polymerization reaction for 4 hours, to obtain a solution containing an acrylic copolymer.
Quality analysis of the obtained acrylic copolymer was performed 1 H-NMR measurement, the content of the structural unit of each monomer was calculated from the integrated intensity ratio of the peaks of hydrogen from each monomer.
The obtained acrylic copolymer was diluted 50 times with Tetrahydrofuran (THF), and the thus obtained diluted solution was filtered through a filter (material: polytetrafluoroethylene, pore size: 0.2 μm) to prepare a measurement sample. The measurement sample was supplied to a gel permeation chromatograph (2690, separations Module, manufactured by Waters corporation), GPC measurement was performed at a sample flow rate of 1mL/min and a column temperature of 40 ℃, and the polystyrene-equivalent molecular weight of the acrylic copolymer was measured to determine the weight average molecular weight.
The acid value of the obtained acrylic copolymer was determined by the potentiometric titration method according to JIS K0070.
The obtained acrylic copolymer was subjected to differential scanning calorimetric measurement using a differential scanning calorimeter (Hitec Science, DSC 7000X), and the glass transition temperature (Tg) was obtained. Specifically, about 2mg of the acrylic copolymer was weighed in an aluminum pan, and the aluminum pan was measured under a nitrogen atmosphere at a temperature of 10 ℃/min. The obtained graph was read to determine the glass transition temperature.
(2) Production of adhesive tape
To the resulting acrylic copolymer-containing solution, 30 parts by weight of terpene phenol B was added to 100 parts by weight of the acrylic copolymer, and the mixture was further added so that the solid content of the isocyanate-based crosslinking agent (CORONATE L-45, manufactured by eastern co.) became 0.5 parts by weight, to prepare a solution containing the adhesive composition. The solution containing the adhesive composition was applied to the release treated surface of the release treated PET film having a thickness of 75 μm so that the thickness of the dried adhesive layer became 50 μm, and then dried at 110 ℃ for 5 minutes. The pressure-sensitive adhesive layer was laminated on the release treated surface of a release treated PET film having a thickness of 75. Mu.m, and cured at 40℃for 48 hours to obtain a pressure-sensitive adhesive tape (non-supporting type).
(3) Determination of acid value
The acid value of the adhesive composition was determined by the potentiometric titration method according to JIS K0070.
(4) Determination of shear storage modulus at 23 DEG C
(4-1) adhesive composition
The adhesive composition was diluted 2 times with ethyl acetate, applied to the release treated surface of the release treated PET film having a thickness of 75 μm so that the thickness after drying became 50. Mu.m, and then dried at 110℃for 5 minutes. The measurement samples were prepared by overlapping the samples so that the thickness became 100. Mu.m. For the measurement of the sample, a dynamic viscoelasticity spectrum was measured at-50℃to 200℃under conditions of 5℃per minute and 10Hz in a shear mode using a viscoelasticity spectrometer (for example, manufactured by IT meter control Co., ltd., DVA-200). From this, the shear storage modulus at 23℃was obtained.
(4-2) adhesive layer
The pressure-sensitive adhesive layers of the pressure-sensitive adhesive tapes were laminated so that the thickness thereof became 100. Mu.m, and a measurement sample was produced. For the measurement of the sample, a dynamic viscoelasticity spectrum was measured at-50℃to 200℃under conditions of 5℃per minute and 10Hz in a shear mode using a viscoelasticity spectrometer (for example, manufactured by IT meter control Co., ltd., DVA-200). From this, the shear storage modulus at 23℃was obtained.
(5) Determination of gel fraction
The release film on one side of the pressure-sensitive adhesive tape was peeled off and bonded to a PET film (FE 2002, manufactured by FUTAMURA CHEMICAL Co.) having a thickness of 23 μm, and cut into a 20mm×40mm planar rectangular shape. Further, a release film on the other side of the adhesive tape was peeled off to prepare a test piece, and the weight was measured. After immersing the test piece in ethyl acetate at 23℃for 24 hours, it was taken out of ethyl acetate and dried at 110℃for 1 hour. The weight of the dried test piece was measured, and the gel fraction was calculated using the following (1).
Gel fraction (wt%) =100× (W 2 -W 0 )/(W 1 -W 0 )(1)
(W 0 : weight of substrate (PET film), W 1 : weight of test piece before immersion, W 2 : weight of the impregnated and dried test piece
Examples 2 to 16 and comparative examples 1 to 4
An adhesive tape was obtained in the same manner as in example 1 except that the types and amounts of the acrylic monomers constituting the acrylic copolymer, the weight average molecular weight of the acrylic copolymer, and the types and amounts of the tackifier resin and the crosslinking agent were changed as shown in table 1.
< evaluation >
The adhesive tapes obtained in examples and comparative examples were evaluated by the following methods. The results are shown in Table 1.
(1) 180 ° peel force to SUS plate
One side (side not to be measured) of the pressure-sensitive adhesive tape was subjected to a gasket with a polyethylene terephthalate film (FE 2002, manufactured by FUTAMURA CHEMICAL Co.) having a thickness of 23 μm, and then cut into test pieces having a width of 25mm and a length of 75 mm. The test piece was placed on the SUS plate with its adhesive layer (side to be measured) facing the SUS plate, and then a rubber roller of 2kg was reciprocated on the test piece at a speed of 300mm/min once to bond the test piece. Then, the mixture was cured at 23℃and 50% humidity for 20 minutes to prepare a test specimen. According to JIS Z0237: 2009, the test specimen was peeled off in the 180℃direction at a stretching speed of 300mm/min under the conditions of 23℃and 50% humidity, and the adhesive force (N/25 mm) was measured.
In table 1, "cohesive failure" means that since the cohesive force of the adhesive layer was low, peeling did not occur at the interface with the SUS plate, and cohesive failure occurred in the adhesive layer.
(2) Corrosion to copper foil
One surface of the pressure-sensitive adhesive tape was subjected to a gasket treatment with a 50 μm thick polyethylene terephthalate film (E5200, manufactured by Toyobo Co., ltd.) and cut into a width of 25 mm. Times.length of 25mm, to prepare a pressure-sensitive adhesive tape for evaluation. 2 of these pressure-sensitive adhesive tapes for evaluation were prepared.
The adhesive surface of the pressure-sensitive adhesive tape 1 for evaluation was placed so as to face one surface of a copper foil (C1020R-H, thickness 20 μm, width 25mm×length 25mm, manufactured by bamboo inner metal foil powder industry co.) and then a rubber roll of 2kg was reciprocated at a speed of 300 mm/min on the pressure-sensitive adhesive tape 1 for evaluation, and bonding was performed. Then, the adhesive surface of the adhesive tape 2 for evaluation was placed so as to face the other surface of the copper foil, and then a 2kg rubber roll was reciprocated at a speed of 300 mm/min on the adhesive tape 2 for evaluation, and the laminate was bonded, thereby producing a laminate having a width of 25mm×a length of 25 mm. After bonding, the laminate was cured at 23℃and 50% humidity for 20 minutes to prepare a test sample.
The test samples were left in an environment at a temperature of 85℃and a humidity of 85%, and after 3 days, 14 days and 28 days, the adhesive tapes 1 and 2 were peeled off from the copper foil, and the presence or absence of corrosion of the copper foil was visually confirmed. The case where corrosion of the copper foil was observed was regarded as x, and the case where corrosion of the copper foil was not observed on both sides was regarded as good.
(3) Carbon content of biological origin
The content of carbon derived from organisms was measured according to ASTM D6866-20 for the adhesive tape.
(4) Haze degree
The adhesive tape was attached to a glass slide (white edge grinder No.2, manufactured by Song Nitro industries Co., ltd.) and a haze meter (HM-150 manufactured by Toku Kogyo Co., ltd.) was used in accordance with JIS K7136: haze was measured at 2000.
TABLE 1
Industrial applicability
According to the present invention, an adhesive composition which is less likely to corrode metals and which can exhibit excellent adhesion can be provided. In addition, according to the present invention, an adhesive tape having an adhesive layer containing the adhesive composition can be provided.
Claims (12)
1. An adhesive composition comprising an acrylic copolymer,
the acrylic copolymer contains 50% by weight or more of a structural unit derived from n-heptyl (meth) acrylate,
the adhesive composition has an acid value of 22mgKOH/g or less and a shear storage modulus at 23 ℃ of 6X 10 4 Pa or more and 5×10 5 Pa or below.
2. The adhesive composition of claim 1, wherein the adhesive composition comprises,
the acid value of the acrylic copolymer is 22mgKOH/g or less.
3. The adhesive composition according to claim 1 or 2, wherein,
the acrylic copolymer further contains a structural unit derived from a monomer having a polar functional group, the monomer having a polar functional group containing a monomer having an amide group.
4. The adhesive composition according to claim 3, wherein,
the content of structural units derived from the amide group-containing monomer of the acrylic copolymer is 2% by weight or more and 30% by weight or less.
5. The adhesive composition according to claim 3 or 4, wherein,
the monomer having a polar functional group further contains a monomer having a hydroxyl group.
6. The adhesive composition of claim 5, wherein the adhesive composition comprises,
the content of structural units derived from the monomer having a hydroxyl group in the acrylic copolymer is 0.01% by weight or more and 5% by weight or less.
7. The adhesive composition according to claim 1, 2, 3, 4, 5 or 6, further comprising a tackifying resin having an acid value of 10mgKOH/g or less.
8. The adhesive composition of claim 7, wherein the adhesive composition comprises,
the hydroxyl value of the tackifying resin is less than 50 mgKOH/g.
9. The adhesive composition according to claim 1, 2, 3, 4, 5, 6, 7 or 8, wherein,
the content of carbon derived from living beings is 30% by weight or more.
10. An adhesive tape comprising an adhesive layer comprising the adhesive composition according to claim 1, 2, 3, 4, 5, 6, 7, 8 or 9.
11. The adhesive tape according to claim 10, wherein,
the gel fraction of the adhesive layer is 20 to 50 wt%.
12. The adhesive tape according to claim 10, wherein,
the gel fraction of the adhesive layer is 60 to 95 wt%.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021-104397 | 2021-06-23 | ||
| JP2021104397 | 2021-06-23 | ||
| PCT/JP2022/025002 WO2022270565A1 (en) | 2021-06-23 | 2022-06-23 | Pressure-sensitive adhesive composition and pressure-sensitive adhesive tape |
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| Publication Number | Publication Date |
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| CN116867868A true CN116867868A (en) | 2023-10-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202280015421.4A Pending CN116867868A (en) | 2021-06-23 | 2022-06-23 | Adhesive composition and adhesive tape |
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| Country | Link |
|---|---|
| JP (1) | JPWO2022270565A1 (en) |
| KR (1) | KR20240023013A (en) |
| CN (1) | CN116867868A (en) |
| TW (1) | TW202309220A (en) |
| WO (1) | WO2022270565A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5463140A (en) * | 1977-10-31 | 1979-05-21 | Nitto Electric Ind Co Ltd | Production of pressure-sensitive adhesive tape |
| CN103620742B (en) * | 2011-07-01 | 2016-05-25 | 古河电气工业株式会社 | Adhesive film, diced chip junction film and use the semiconductor processing method of this diced chip junction film |
| DE102012201913A1 (en) * | 2012-02-09 | 2013-08-14 | Tesa Se | Pressure-sensitive adhesive tapes based on bio-based monomers |
| JP2015021067A (en) | 2013-07-19 | 2015-02-02 | Dic株式会社 | Thermally conductive adhesive tape, article and image display device |
| JP6100654B2 (en) | 2013-09-06 | 2017-03-22 | 帝人株式会社 | Heat-resistant adhesive tape substrate and heat-resistant adhesive tape comprising the same |
| JP6367599B2 (en) | 2013-11-22 | 2018-08-01 | 日東電工株式会社 | Double-sided adhesive sheet |
| US20210395575A1 (en) * | 2018-06-19 | 2021-12-23 | Sekisui Chemical Co., Ltd. | Adhesive agent, adhesive tape, and method for affixing electronic components or vehicle-mounted components |
| JP7449138B2 (en) * | 2019-03-28 | 2024-03-13 | 積水化学工業株式会社 | Pressure sensitive adhesive composition and adhesive tape |
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- 2022-06-23 TW TW111123455A patent/TW202309220A/en unknown
- 2022-06-23 CN CN202280015421.4A patent/CN116867868A/en active Pending
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| WO2022270565A1 (en) | 2022-12-29 |
| JPWO2022270565A1 (en) | 2022-12-29 |
| TW202309220A (en) | 2023-03-01 |
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