CN116368198A - Adhesive composition for pavement or floor and marking sheet - Google Patents
Adhesive composition for pavement or floor and marking sheet Download PDFInfo
- Publication number
- CN116368198A CN116368198A CN202180064969.3A CN202180064969A CN116368198A CN 116368198 A CN116368198 A CN 116368198A CN 202180064969 A CN202180064969 A CN 202180064969A CN 116368198 A CN116368198 A CN 116368198A
- Authority
- CN
- China
- Prior art keywords
- meth
- mass
- adhesive composition
- monomer
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 83
- 239000000853 adhesive Substances 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 239000000178 monomer Substances 0.000 claims abstract description 90
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 65
- 239000011347 resin Substances 0.000 claims abstract description 54
- 229920005989 resin Polymers 0.000 claims abstract description 54
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 30
- 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 claims abstract description 30
- 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 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 7
- -1 polyethylene terephthalate Polymers 0.000 claims description 61
- 239000003431 cross linking reagent Substances 0.000 claims description 46
- 239000000463 material Substances 0.000 claims description 44
- 239000012790 adhesive layer Substances 0.000 claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 35
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 239000011888 foil Substances 0.000 claims description 10
- 239000004800 polyvinyl chloride Substances 0.000 claims description 9
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 8
- 239000004642 Polyimide Substances 0.000 claims description 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 7
- 229920001721 polyimide Polymers 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 70
- 239000010410 layer Substances 0.000 description 53
- 239000012948 isocyanate Substances 0.000 description 24
- 150000002513 isocyanates Chemical class 0.000 description 24
- 206010040844 Skin exfoliation Diseases 0.000 description 20
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 18
- 238000012546 transfer Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000010426 asphalt Substances 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 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 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000013522 chelant Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000004971 Cross linker Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VXTYNAYYDYWUSP-UHFFFAOYSA-N 1,1-ditert-butyl-4-(4,4-ditert-butylcyclohexyl)peroxycyclohexane Chemical compound C(C)(C)(C)C1(CCC(CC1)OOC1CCC(CC1)(C(C)(C)C)C(C)(C)C)C(C)(C)C VXTYNAYYDYWUSP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- TYZFMFVWHZKYSE-UHFFFAOYSA-N 3-mercaptohexanol Chemical compound CCCC(S)CCO TYZFMFVWHZKYSE-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- QYUWTCWEBOOMCX-UHFFFAOYSA-N 4-[4,4-bis(2,4,4-trimethylpentan-2-yl)cyclohexyl]peroxy-1,1-bis(2,4,4-trimethylpentan-2-yl)cyclohexane Chemical compound CC(C)(C)CC(C)(C)C1(CCC(CC1)OOC2CCC(CC2)(C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C QYUWTCWEBOOMCX-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 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 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
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- 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 1
- KHKRRUCBBICAJR-UHFFFAOYSA-N (2-hydroxy-3-oxopent-4-enyl) dihydrogen phosphate Chemical compound OC(COP(O)(O)=O)C(=O)C=C KHKRRUCBBICAJR-UHFFFAOYSA-N 0.000 description 1
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
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- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- WTNTZFRNCHEDOS-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NCCO WTNTZFRNCHEDOS-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- KNZIIQMSCLCSGZ-UHFFFAOYSA-N non-1-enylbenzene Chemical compound CCCCCCCC=CC1=CC=CC=C1 KNZIIQMSCLCSGZ-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- RCALDWJXTVCBAZ-UHFFFAOYSA-N oct-1-enylbenzene Chemical compound CCCCCCC=CC1=CC=CC=C1 RCALDWJXTVCBAZ-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical compound CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- AAYRWMCIKCRHIN-UHFFFAOYSA-N propane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CCCS(O)(=O)=O AAYRWMCIKCRHIN-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- 150000003440 styrenes Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/082—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising vinyl resins; comprising acrylic resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
-
- 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
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
-
- 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
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/28—Metal sheet
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The adhesive composition for road surfaces or ground surfaces comprises a (meth) acrylic copolymer (A) and a rosin-based tackifying resin (B), wherein the (meth) acrylic copolymer (A) is a copolymer comprising 20 to 69 mass% of a (meth) acrylic acid alkyl ester monomer (a 1) having an alkyl group of 1 to 7 carbon atoms, 30 to 74 mass% of a (meth) acrylic acid alkyl ester monomer (a 2) having an alkyl group of 8 to 20 carbon atoms and 1 to 6 mass% of a monomer component containing an acid group monomer (a 3), the content of the resin (B) is 10 to 30 parts by mass based on 100 parts by mass of the copolymer (A), and the proportion of the component having a molecular weight of 5000 or less in the copolymer (A) is 1.5 mass% or less.
Description
Technical Field
The present invention relates to an adhesive composition for pavement or ground and a marking sheet.
Background
The marking sheet for road surface or ground surface is attached to a road surface or ground surface of a road/parking lot or the like in or out of a room, and is used on the road surface or ground surface of the road/parking lot or the like (hereinafter, sometimes referred to as "road surface or the like") for the purpose of displaying information such as propaganda, direction indication, traffic sign, guidance or the like.
The marking sheet to be attached to such a road surface or the like is constituted by, for example, using a vinyl chloride sheet as a base material, providing an adhesive layer for attaching to the road surface or the like on one surface of the base material, and forming a decorative layer for imparting characters, figures, or the like related to desired information on the other surface of the base material.
The pavement marking sheet is used in an environment where repeated vehicle travel is received while being subjected to long-term outdoor weather, sunlight, and the like. The floor marking sheet is used in an environment where the floor marking sheet is continuously subjected to friction, impact, or the like caused by a cleaning operation, a shoe sole of a pedestrian, or the like. Therefore, the label sheet attached to the road surface or the like may cause a problem that the label sheet itself is injured or peeled off from the road surface or the like.
On the other hand, when the marking sheet is provided in a high-temperature environment for a long period of time, the adhesion of the adhesive layer of the marking sheet to the road surface is higher than that of the base material, and the adhesive layer remains on the road surface side when the marking sheet is peeled off, which causes a problem of road surface pollution.
To solve such problems, development of a laminate comprising an adhesive agent, an adhesive layer, and a base material has been advanced in order to prevent deterioration of a pavement or floor marking sheet.
In addition, a marking sheet for road surfaces or ground surfaces generally needs adhesion, weather resistance, heat resistance, and moist heat resistance in addition to following up to rough surfaces having irregularities such as asphalt. In order to exhibit the following property with respect to asphalt and the like, use of a metal base material such as aluminum has been studied. In the case of using such a metal base material, it is conceivable to copolymerize a monomer having an acidic group having a strong interaction with a metal as a component of the adhesive layer.
For example, patent document 1 discloses an adhesive composition for an adherend which is difficult to adhere and contains an acrylic resin (a) obtained by copolymerizing a copolymer component (a) of a terminal carboxyl group-containing monomer (a 1) and a (meth) acrylic acid (a 2).
Patent document 2 discloses a road/ground marking sheet comprising a marking sheet main body and a road/ground marking laminate sheet, wherein the marking sheet main body includes a first adhesive layer, a metal layer, a second adhesive layer, a base material, and a decorative layer, and the road/ground marking laminate sheet is adhered to a surface of the marking sheet main body opposite to a road surface side (first adhesive layer).
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2019-151837
Patent document 2: japanese patent laid-open No. 2015-184388
Disclosure of Invention
Technical problem to be solved by the invention
In patent document 1, a modified asphalt or the like is exemplified as an adherend of an adhesive tape. However, the adhesive composition of patent document 1 does not describe the adhesion between the adhesive layer and the metal layer in the laminate having the metal layer, and the resistance of the adhesive to the road surface (asphalt) as an adherend, that is, the excellent re-peelability to the road surface, to the road surface contamination.
Patent document 2 discloses a laminate comprising an adhesive layer using an acrylic adhesive and a base material composed of polyvinyl chloride, an adipic acid polyester plasticizer, a calcium-zinc stabilizer and a thermoplastic polyurethane elastomer, wherein the laminate is excellent in impact alleviation and the decorative layer can maintain good recognition from the viewpoint of adhesion and durability. However, there is no description about the re-peelability to the road surface.
In view of the above problems, an object of the present invention is to provide an adhesive composition which is excellent in adhesion, peeling resistance, heat resistance, and wet heat resistance in addition to following properties to a rough surface such as asphalt, and the like, and which is excellent in adhesion between a substrate and an adhesive layer, and which can inhibit an adhesive from being transferred from the substrate to an adherend during peeling.
Means for solving the technical problems
The present inventors have conducted intensive studies in order to solve the above-mentioned problems. As a result, it has been found that the above-mentioned technical problems can be solved by an adhesive composition comprising a specific (meth) acrylic copolymer and a specific tackifying resin in specific amounts, and the present invention has been completed.
The present invention relates to, for example, the following [1] to [7].
[1] A pressure-sensitive adhesive composition for road surfaces or for floor surfaces, which comprises a (meth) acrylic copolymer (A) and a rosin-based tackifying resin (B), wherein the (meth) acrylic copolymer (A) comprises 20 to 69 mass% of a (meth) acrylic alkyl ester monomer (a 1) having 1 to 7 alkyl groups, 30 to 74 mass% of a (meth) acrylic alkyl ester monomer (a 2) having 8 to 20 alkyl groups, and 1 to 6 mass% of a monomer component containing an acid group monomer (a 3), the total of the components (a 1) to (a 3) being 100 mass%, and the content of the rosin-based tackifying resin (B) being 10 to 30 mass% relative to 100 mass parts of the (meth) acrylic copolymer (A), and the proportion of the component having a molecular weight of 5000 or less in the (meth) acrylic copolymer (A) being 1.5 mass% or less.
[2] The adhesive composition for road surfaces or floor surfaces according to the above [1], wherein the softening point of the rosin-based tackifying resin is 120℃or higher.
[3] The adhesive composition for road surfaces or floor surfaces according to the above [1] or [2], wherein the adhesive composition further comprises a crosslinking agent (C).
[4] A marking sheet for road surfaces or floors comprising an adhesive layer formed of the adhesive composition according to any one of the above [1] to [3], and a metal base material.
[5] The pavement or ground marking sheet according to item [4], wherein the metal base material is aluminum foil.
[6] The marking sheet for road or floor according to the above [4] or [5], wherein a plastic base material is further provided.
[7] The marking sheet for road or floor according to item [6], wherein the plastic substrate is at least one substrate selected from the group consisting of polyvinyl chloride, polyethylene terephthalate, polyethylene and polyimide.
Effects of the invention
According to the present invention, there can be provided an adhesive composition which is excellent in adhesion, peeling resistance, heat resistance and wet heat resistance in addition to following properties to a rough surface such as asphalt, etc., and which is excellent in adhesion between a substrate and an adhesive layer and can suppress transfer of an adhesive from the substrate to an adherend at the time of peeling.
Drawings
Fig. 1 is a schematic view showing a specific example of a layer structure of a marking sheet of the present invention.
Detailed Description
The present invention will be specifically described below.
In the present specification, (meth) acrylic acid is used in the generic terms of acrylic acid and methacrylic acid, and may be acrylic acid or methacrylic acid, and (meth) acrylic acid ester is used in the generic terms of acrylic acid ester and methacrylic acid ester, and may be acrylic acid ester or methacrylic acid ester.
[ adhesive composition for road surface or floor surface ]]
The adhesive composition for road surfaces or floors (hereinafter, may be simply referred to as "adhesive composition") of the present invention comprises the (meth) acrylic copolymer (a) and the rosin-based tackifying resin (B) described below, respectively.
(meth) acrylic copolymer (A) >
The (meth) acrylic copolymer (A) is a copolymer containing 20 to 69 mass% of a monomer component comprising an alkyl (meth) acrylate monomer (a 1) having an alkyl group of 1 to 7 carbon atoms, 30 to 74 mass% of an alkyl (meth) acrylate monomer (a 2) having an alkyl group of 8 to 20 carbon atoms, and 1 to 6 mass% of an acid group-containing monomer (a 3).
Alkyl (meth) acrylate monomer (a 1)
The (meth) acrylic copolymer (A) contains an alkyl (meth) acrylate monomer (a 1) having 1 to 7 alkyl carbons (hereinafter also referred to as "monomer (a 1)")
Examples of the "alkyl" having 1 to 7 carbon atoms may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl and n-heptyl. The alkyl group may be straight chain or branched.
Examples of the monomer (a 1) having 1 to 7 carbon atoms as the alkyl group include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, isobutyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, sec-butyl (meth) acrylate, n-pentyl (meth) acrylate, neopentyl (meth) acrylate, isopentyl (meth) acrylate, n-hexyl (meth) acrylate, and n-heptyl (meth) acrylate.
Among them, n-butyl (meth) acrylate and t-butyl (meth) acrylate are preferable as the monomer (a 1).
The monomer (a 1) may be used alone or in combination of 1 or more than 2.
Alkyl (meth) acrylate monomer (a 2)
The (meth) acrylic copolymer (a) contains an alkyl (meth) acrylate monomer (a 2) having an alkyl group having 8 to 20 carbon atoms (hereinafter also referred to as "monomer (a 2)").
Examples of the "alkyl" having 8 to 20 carbon atoms may include 2-ethylhexyl, n-octyl, isooctyl, 1-methylheptyl, n-decyl, isodecyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 2, 6-dimethyl-4-heptyl, 3, 5-trimethylhexyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicosyl. The alkyl group may be linear or branched.
Examples of the monomer (a 2) having 8 to 20 carbon atoms in the alkyl group include 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, isostearyl (meth) acrylate, n-nonadecyl (meth) acrylate, isononadecyl (meth) acrylate, and n-eicosyl (meth) acrylate.
Among them, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, and isooctyl (meth) acrylate are preferable as the monomer (a 2).
The monomer (a 2) may be used alone or in combination of 1 kind or 2 or more kinds.
In the monomer component, the mass ratio of the monomer (a 1) to the monomer (a 2) is preferably 1:0.6 to 1:2.2, more preferably 1:0.7 to 1:1.5. The adhesive composition comprising the (meth) acrylic copolymer (a) using the monomer (a 1) and the monomer (a 2) in the above-mentioned ranges is excellent in the balance between adhesion to a substrate and cohesive force.
Acid group-containing monomer (a 3)
The (meth) acrylic copolymer (a) contains an acid group-containing monomer (a 3) (hereinafter also referred to as "monomer (a 3)").
Examples of the acid group-containing monomer (a 3) include a carboxyl group-containing monomer, a sulfonic acid group-containing monomer, and a phosphoric acid group-containing monomer, and a carboxyl group-containing monomer is preferable.
The carboxyl group-containing monomer is a monomer having a carboxyl group in the molecule. Specific examples of the carboxyl group-containing monomer include acrylic acid, methacrylic acid, β -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl succinate, ω -carboxypolycaprolactone mono (meth) acrylate, crotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, and the like.
The sulfonic acid group-containing monomer is a monomer having a sulfonic acid group in the molecule. Specific examples of the sulfonic acid group-containing monomer include styrene sulfonic acid, allyl sulfonic acid, propyl (meth) acrylate, 2- (meth) acrylamide-2-methylpropanesulfonic acid, (meth) acrylamide propane sulfonic acid, and (meth) acryloxynaphthalene sulfonic acid.
The phosphate group-containing monomer is a monomer having a phosphate group in the molecule. Specific examples of the phosphoric acid group-containing monomer include acryl-2-hydroxyethyl phosphate.
Among them, as the monomer (a 3), at least one monomer selected from acrylic acid, methacrylic acid, β -carboxyethyl (meth) acrylate is preferably used, and at least one monomer selected from acrylic acid and methacrylic acid is more preferably used. These monomers are readily available industrially and are therefore preferred.
The monomer (a 3) may be used alone or in combination of 1 kind or 2 or more kinds.
<Monomer component of (meth) acrylic copolymer (A)>
The monomer component constituting the (meth) acrylic copolymer (a) is 20 to 69 mass%, preferably 25 to 63.5 mass%, more preferably 30 to 58 mass% of the alkyl (meth) acrylate monomer (a 1), 30 to 74 mass%, preferably 35 to 69 mass%, more preferably 40 to 65 mass% of the alkyl (meth) acrylate monomer (a 2), and 1 to 6 mass%, preferably 1.5 to 6 mass%, more preferably 2 to 5 mass% of the acid group-containing monomer (a 3). Wherein the total of the components (a 1) to (a 3) is 100% by mass.
By using the monomer (a 1) and the monomer (a 2) in the above-described range, an adhesive composition excellent in balance between adhesion and cohesive force can be obtained. The pressure-sensitive adhesive composition using the acid group-containing monomer (a 3) in the above range is preferable because of improved heat resistance, moist heat resistance and adhesion to a metal substrate. If the monomer (a 3) in the (meth) acrylic copolymer (a) exceeds the above range, the release property is poor due to a large amount of adhesive residue on the road surface when the marking sheet using the adhesive composition is released from the road surface, which is not preferable.
The (meth) acrylic copolymer (a) obtained by using the monomers in the above-mentioned ranges has excellent compatibility with the rosin-based tackifying resin (B), and the adhesive layer formed from the adhesive composition of the present invention is considered to be dispersed in the whole layer. The adhesive layer is excellent in stress relaxation property and heat resistance because the rosin-based tackifying resin (B) is dispersed throughout the layer.
Other monomer (a 4)
The (meth) acrylic polymer (a) may further contain a monomer (a 4) other than the above monomers (a 1) to (a 3). Examples of the other monomer (a 4) include: hydroxyl group-containing monomers, (meth) acrylic esters containing alicyclic hydrocarbon groups or aromatic hydrocarbon groups, alkoxypolyalkylene glycol mono (meth) acrylic esters, styrenic monomers, amide group-containing monomers, amino group-containing monomers, cyano group-containing monomers, vinyl acetate.
Examples of the hydroxyl group-containing monomer include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxyundecyl (meth) acrylate, 4-hydroxymethylcyclohexyl (meth) acrylate, N-methylol (meth) acrylamide, vinyl alcohol, allyl alcohol, 2-hydroxyethylvinyl ether, 4-hydroxybutyl vinyl ether, and the like. Among them, 2-hydroxyethyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate are preferably used.
Examples of the alicyclic hydrocarbon group-or aromatic hydrocarbon group-containing (meth) acrylate include: cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate.
Examples of the alkoxy polyalkylene glycol mono (meth) acrylate include: methoxy diethylene glycol mono (meth) acrylate, methoxy dipropylene glycol mono (meth) acrylate, ethoxy triethylene glycol mono (meth) acrylate, ethoxy diethylene glycol mono (meth) acrylate, methoxy triethylene glycol mono (meth) acrylate.
Examples of the styrene monomer include: styrene; alkylstyrenes such as methylstyrene, dimethylstyrene, trimethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, octylstyrene and the like; halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, etc.; and functional styrene such as nitrostyrene, acetylstyrene, methoxystyrene, etc.
Examples of the amide group-containing monomer include: n, N-dialkyl (meth) acrylamides such as (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-hexyl (meth) acrylamide, and N, N-dimethyl (meth) acrylamide; n-vinyl pyrrolidone, N-vinyl caprolactam, and (meth) acryloylmorpholine.
Examples of the amino group-containing monomer include: n, N-dialkylaminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate and N, N-diethylaminoethyl (meth) acrylate.
Examples of the cyano group-containing monomer include: cyano (meth) acrylate, (meth) acrylonitrile.
The monomer (a 4) may be used alone or in combination of 1 kind or 2 or more kinds.
The monomer (a 4) is an optional component, and the content of the monomer (a 4) is preferably 20 mass% or less, more preferably 15 mass% or less, and still more preferably 10 mass% or less, based on 100 mass% of the monomer component for forming the copolymer (a).
<Physical Properties of (meth) acrylic copolymer (A)>
The weight average molecular weight (Mw) of the (meth) acrylic copolymer (A) is preferably 20 to 150 million, more preferably 25 to 130 million, still more preferably 35 to 120 million. In the case where the Mw is within the above range, sufficient cohesive force is imparted to the pressure-sensitive adhesive sheet obtained from the pressure-sensitive adhesive composition, and therefore, the pressure-sensitive adhesive sheet is preferable in view of improvement in durability under high temperature conditions or high temperature and high humidity conditions.
The weight average molecular weight (Mw) was determined by Gel Permeation Chromatography (GPC). The measurement conditions of GPC are described in detail in the examples column described later.
The molecular weight distribution (Mw/Mn) of the (meth) acrylic copolymer (A) as measured by GPC is preferably 2 to 13, more preferably 2.5 to 10, still more preferably 2.8 to 8.Mw/Mn in the above range is preferable from the viewpoints of durability and re-peelability.
The proportion of the (meth) acrylic copolymer (low molecular weight component) having a molecular weight of 5000 or less in the (meth) acrylic copolymer (a) is preferably 1.5% by mass or less, more preferably 1.0% by mass or less, and particularly preferably 0.6% by mass or less. The lower limit of the proportion of the component having a molecular weight of 5000 or less is not particularly limited, but is usually 0.01 mass% or more. The above ratio is a ratio of components having a molecular weight of 5000 or less when the total molecular weight of the (meth) acrylic copolymer (a) is 100 mass%. The above ratio can be determined by obtaining an integral molecular weight distribution curve by GPC. The proportion of the component having a molecular weight of 5000 or less in the (meth) acrylic copolymer (a) is preferably in the above range, since a marking sheet for road surfaces or ground surfaces having less adhesive residue on road surfaces and excellent removability can be obtained. If the proportion of the component having a molecular weight of 5000 or less exceeds 1.5 mass%, a layer derived from the low-molecular-weight component tends to be formed at the interface between the pressure-sensitive adhesive layer and the adherend when the pressure-sensitive adhesive sheet is adhered to the adherend, and the adhesiveness and heat resistance are lowered, which is not preferable.
<Production of (meth) acrylic copolymer (A)>
The (meth) acrylic copolymer (a) can be produced by a conventionally known polymerization method such as a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, or a suspension polymerization method, and among these, the solution polymerization method is preferable.
Specifically, the monomer component, a chain transfer agent, a polymerization solvent, etc. which are optionally used, are added to a reaction vessel, a polymerization initiator is added under an inert gas atmosphere such as nitrogen, the reaction initiation temperature is set to be usually 40 to 100 ℃, preferably 50 to 80 ℃, and the reaction system is maintained at a temperature of usually 50 to 90 ℃, preferably 60 to 90 ℃ for 2 to 20 hours. In the polymerization reaction, a polymerization initiator, a chain transfer agent, a monomer component, and a polymerization solvent may be added as appropriate. The polymerization initiator may be an azo initiator or a peroxide polymerization initiator.
Examples of the azo initiator include: 2,2 '-azobisisobutyronitrile, 2' -azobis (4-methoxy-2, 4-dimethylvaleronitrile), 2 '-azobis (2-cyclopropylpropionitrile), 2' -azobis (2, 4-dimethylvaleronitrile), 2 '-azobis (2-methylbutyronitrile), 1,1' -azobis (cyclohexane-1-carbonitrile), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2, 4-dimethylvaleronitrile, 2 '-azobis (2-aminodipropane) dihydrochloride, 2' -azobis (N, azo compounds such as N '-dimethylisobutyramidine), 2' -azobis [ 2-methyl-N- (2-hydroxyethyl) -propionamide ], 2 '-azobis (isobutylamide) dihydrate, 4' -azobis (4-cyanovaleric acid), 2 '-azobis (2-cyanopropanol), and dimethyl-2, 2' -azobis (2-methylpropionate).
Examples of the peroxide-based polymerization initiator include: tert-butylhydroperoxide, cumene hydroperoxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, hexanoyl peroxide, diisopropyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, tert-butyl peroxypivalate, 2-bis (4, 4-di-tert-butylcyclohexyl peroxide) propane 2, 2-bis (4, 4-di-tert-amylcyclohexyl peroxide) propane, 2-bis (4, 4-di-tert-octylcyclohexyl peroxide) propane, 2-bis (4, 4-di-a-isopropylphenylcyclohexyl peroxide) propane, 2-bis (4, 4-di-tert-butylcyclohexyl peroxide) butane, 2-bis (4, 4-di-tert-octylcyclohexyl peroxide) butane.
The polymerization initiator may be used alone or in an amount of 1 kind or 2 or more kinds.
In the production of the (meth) acrylic copolymer (a), the amount of the polymerization initiator is usually in the range of 0.001 to 5 parts by mass, preferably 0.005 to 3 parts by mass, relative to 100 parts by mass of the total of the monomer components for forming the (meth) acrylic copolymer (a).
Examples of the chain transfer agent include: 2-mercaptoethanol, thioglycerol, 3-mercapto-1-hexanol, thioglycollic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 4-mercaptobutyric acid, 6-mercaptohexanoic acid, 11-mercaptoundecanoic acid, 3-mercaptopyruvic acid, 2-mercaptobenzoic acid, 3-mercaptobenzoic acid, 4-mercaptobenzoic acid, thiomalic acid, n-dodecyl mercaptan, pentaerythritol tetrakis (3-mercaptopropionate), alpha-methylstyrene dimer, naphthoquinone-based compound.
The chain transfer agent may be used alone in an amount of 1 or 2 or more.
When the chain transfer agent is used, the amount of the chain transfer agent is preferably in the range of 0.01 to 5 parts by mass, more preferably 0.02 to 3 parts by mass, and even more preferably 0.03 to 2.5 parts by mass, based on 100 parts by mass of the monomer component for forming the (meth) acrylic copolymer (a).
Examples of the polymerization solvent used in the solution polymerization include: aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane, and n-octane; alicyclic hydrocarbons such as cyclopentane, cyclohexane, cycloheptane, cyclooctane and the like; ethers such as diethyl ether, diisopropyl ether, 1, 2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenetole, and diphenyl ether; halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1, 2-dichloroethane, chlorobenzene, and the like; esters such as ethyl acetate, propyl acetate, butyl acetate, methyl propionate; ketones such as acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, and cyclohexanone; amides such as N, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone; nitriles such as acetonitrile and benzonitrile; sulfoxides such as dimethyl sulfoxide and sulfolane.
The polymerization solvent may be used alone or in combination of 1 or more than 2.
< rosin-based tackifying resin (B) >)
The rosin-based tackifying resin (B) may be used without limitation as a resin having a softening point of 120 ℃ or higher, but from the viewpoint of imparting stress relaxation properties in a high-temperature environment, the softening point is preferably 120 to 200 ℃, more preferably 120 to 160 ℃.
The rosin-based tackifying resin (B) having a softening point of 120 ℃ or higher may be exemplified by: PENSEL C (softening point 120 ℃), PENSEL D-125 (softening point 125 ℃), PENSEL D-135 (softening point 135 ℃), PENSEL D-160 (softening point 160 ℃), SUPER ESTER A-125 (softening point 125 ℃) and the like manufactured by the Nakawa chemical industries, inc. Further, HARITACK PCJ (softening point 123 ℃) manufactured by Ha Lima chemical group Co., ltd.), HARITACK DP-2669 (softening point 135 ℃) and HARITACK FK (softening point 125 ℃) are mentioned.
The adhesive composition of the present invention contains the (meth) acrylic copolymer (a) and the rosin-based resin (B) in specific amounts at the same time, and therefore the adhesive layer obtained from the adhesive composition is less in adhesive residue when peeled from a road surface or the like, and is excellent in re-peelability to a road surface or the like.
In the adhesive composition of the present invention, the content of the rosin-based tackifying resin (B) is 10 to 30 parts by mass, preferably 18 to 28 parts by mass, more preferably 20 to 26 parts by mass, per 100 parts by mass of the (meth) acrylic copolymer (a).
< crosslinker (C) >
The adhesive composition of the present invention preferably contains a crosslinking agent (C) in addition to the (meth) acrylic copolymer (A) and the rosin-based tackifying resin (B). For example, the (meth) acrylic copolymer (a) may be crosslinked with a crosslinking agent (C) to obtain an adhesive composition.
The crosslinking agent may be used without particular limitation, and for example, an isocyanate crosslinking agent, a metal chelate crosslinking agent, an epoxy crosslinking agent may be used. As the crosslinking agent (C), 1 kind may be used alone, or 2 or more kinds may be used.
As the crosslinking agent (C), at least one selected from the group consisting of an isocyanate crosslinking agent (C-1) and a metal chelate crosslinking agent (C-2) is preferable, and an isocyanate crosslinking agent (C-1) or a metal chelate crosslinking agent (C-2) is preferable, and an isocyanate crosslinking agent (C-1) is more preferable. The isocyanate crosslinking agent (C-1) is preferable because of excellent adhesion between the pressure-sensitive adhesive layer and the substrate, and the metal chelate crosslinking agent (C-2) is preferable because the curing time can be shortened.
Isocyanate crosslinking agent (C-1)
As the isocyanate crosslinking agent (C-1), an isocyanate crosslinking agent having an isocyanate number of 2 or more in 1 molecule is generally used. The (meth) acrylic copolymer (A) is crosslinked with the isocyanate crosslinking agent (C-1) to form a crosslinked body (network polymer).
The isocyanate crosslinking agent (C-1) has an isocyanate number of usually 2 or more, preferably 2 to 8, more preferably 3 to 6. The number of isocyanate groups in the above range is preferable from the viewpoint of the crosslinking reaction efficiency of the (meth) acrylic copolymer (A) and the isocyanate crosslinking agent (C-1) and from the viewpoint of maintaining the flexibility of the adhesive layer.
Examples of the diisocyanate crosslinking agent having an isocyanate number of 2 in 1 molecule include: aliphatic diisocyanates, cycloaliphatic diisocyanates, aromatic diisocyanates. Examples of the aliphatic diisocyanate include aliphatic diisocyanates having 4 to 30 carbon atoms such as ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1, 5-pentane diisocyanate, 3-methyl-1, 5-pentane diisocyanate, and 2, 4-trimethyl-1, 6-hexamethylene diisocyanate.
Examples of the alicyclic diisocyanate include: alicyclic diisocyanates having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylene diisocyanate, hydrogenated toluene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylene diisocyanate.
As the aromatic diisocyanate, there may be exemplified: aromatic diisocyanates having 8 to 30 carbon atoms such as benzene diisocyanate, toluene diisocyanate, xylene diisocyanate, naphthalene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
Examples of the isocyanate crosslinking agent having 3 or more isocyanate groups in 1 molecule include: aromatic polyisocyanates, aliphatic polyisocyanates, cycloaliphatic polyisocyanates. Specific examples include: 2,4, 6-triisocyanate toluene, 1,3, 5-triisocyanate benzene, 4' -triphenylmethane triisocyanate.
Further, as the isocyanate crosslinking agent (C-1), there may be mentioned: polymers (e.g., 2 or 3 polymers, biuret, isocyanurate) and derivatives (e.g., addition reaction products of polyols and 2 or more molecules of diisocyanate crosslinkers) of the above isocyanate crosslinkers having an isocyanate number of 2 or more. Examples of the "polyol" in the above derivatives include tri-or higher alcohols such as trimethylolpropane, glycerol and pentaerythritol; the high molecular weight polyol may, for example, be a polyether polyol, a polyester polyol, an acrylic polyol, a polybutadiene polyol or a polyisoprene polyol.
Examples of such isocyanate crosslinking agents include: trimers of diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanates, biuret or isocyanurate bodies of hexamethylene diisocyanate or toluene diisocyanate, reaction products of trimethylolpropane with toluene diisocyanate or xylene diisocyanate (e.g. 3-molecular adducts of toluene diisocyanate or xylene diisocyanate), reaction products of trimethylolpropane with hexamethylene diisocyanate (e.g. 3-molecular adducts of hexamethylene diisocyanate), polyether polyisocyanates, polyester polyisocyanates.
Among the isocyanate crosslinking agents (C-1), a reaction product of trimethylolpropane and toluene diisocyanate (such as L-45K manufactured by Zodiac Co., ltd.), a reaction product of trimethylolpropane and xylene diisocyanate (such as TD-75 manufactured by Zodiac Co., ltd.), and an isocyanurate of hexamethylene diisocyanate or toluene diisocyanate (such as TSE-100 manufactured by Asahi Kabushiki Kaisha, CORONATE 2050 manufactured by Tosoh Co., ltd.) are preferable from the viewpoint of good balance of adhesive properties and high durability.
The isocyanate crosslinking agent (C-1) may be used alone or in combination of 1 or more than 2.
In the adhesive composition of the present invention, the content of the isocyanate crosslinking agent (C-1) is preferably 1 to 5 parts by mass, more preferably 1.2 to 4.5 parts by mass, and even more preferably 1.5 to 4 parts by mass, per 100 parts by mass of the solid content of the (meth) acrylic copolymer (a).
Metal chelate Cross-linking agent (C-2)
Examples of the metal chelate crosslinking agent (C-2) include compounds obtained by coordinating an alkoxide, acetylacetone, ethyl acetoacetate, or the like with a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, zirconium, or the like.
Among them, aluminum chelates (M-5 ADT, manufactured by Zostera chemical Co., ltd.) are particularly preferable. Specific examples thereof include aluminum isopropoxide, aluminum sec-butyrate, aluminum acetoacetate diisopropoxide, aluminum triacetoacetate, and aluminum triacetylacetonate.
The metal chelate crosslinking agent (C-2) may be used alone or in combination of 1 or more than 2.
In the adhesive composition of the present invention, the content of the metal chelate crosslinking agent (C-2) is preferably 0 to 1 part by mass, more preferably 0 to 0.5 part by mass, and even more preferably 0 to 0.2 part by mass, per 100 parts by mass of the (meth) acrylic copolymer (a).
Epoxy Cross-linking agent (C-3)
As the epoxy crosslinking agent (C-3), for example, an epoxy compound having an epoxy number of 2 or more in 1 molecule is generally used. For example, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerol triglycidyl ether, 1, 3-bis (N, N-diglycidyl aminomethyl) cyclohexane, N, N, N ', N' -tetraglycidyl metaxylene diamine, N, N, N ', N' -tetraglycidyl aminophenyl methane, triglycidyl isocyanurate, m-N, N-diglycidyl aminophenyl glycidyl ether, N-diglycidyl toluidine, N-diglycidyl aniline. The epoxy crosslinking agent (C-3) may be used alone or in combination of 1 or more than 2.
In the adhesive composition of the present invention, the content of the epoxy crosslinking agent (C-3) is preferably 0.01 to 1 part by mass, more preferably 0.03 to 0.8 part by mass, and even more preferably 0.05 to 0.5 part by mass, per 100 parts by mass of the (meth) acrylic copolymer (A).
In the adhesive composition of the present invention, the content of the crosslinking agent (C) is 0.01 to 5 parts by mass, preferably 0.03 to 4.5 parts by mass, more preferably 0.05 to 4 parts by mass, per 100 parts by mass of the (meth) acrylic copolymer (a).
< other Components >)
Tackifying resin (D)
The adhesive composition of the present invention may further comprise, as an optional component, a tackifying resin (D) other than the rosin-based tackifying resin (B) having a softening point of 120 ℃ or higher. The tackifying resin (D) is not particularly limited as long as it is a resin other than the rosin-based tackifying resin (B).
In the pressure-sensitive adhesive composition of the present invention, the content of the tackifier resin (D) is preferably 0 to 10 parts by mass, more preferably 0 to 8 parts by mass, still more preferably 0 to 6 parts by mass, and particularly preferably 0 to 5 parts by mass, per 100 parts by mass of the (meth) acrylic copolymer (a). In addition, the adhesive composition of the present invention preferably contains substantially no tackifying resin (D) from the viewpoint of stress relaxation property at high temperature, cohesive force and tackiness. By substantially free, it is meant that the adhesive composition comprises 0 parts by mass or more and less than 0.01 parts by mass of tackifying resin (D) relative to 100 parts by mass of (meth) acrylic copolymer (a).
The tackifying resin (D) includes at least one tackifying resin selected from the group consisting of styrene resins, C9 petroleum resins, hydrogenated petroleum resins, terpene resins, phenol resins, and rosin tackifying resins having a softening point of less than 120 ℃. As the tackifying resin (D), 1 kind may be used alone, or 2 or more kinds may be used.
The amount of the tackifying resin contained in the adhesive composition of the present invention, that is, the total amount of the rosin-based tackifying resin (B) and the tackifying resin (D), is preferably within the following range. In the pressure-sensitive adhesive composition of the present invention, the content of the tackifier resin is preferably more than 16 parts by mass and less than 35 parts by mass, more preferably 18 to 33 parts by mass, and particularly preferably 20 to 30 parts by mass, per 100 parts by mass of the (meth) acrylic copolymer (a). The above range is preferable because it is compatible with the (meth) acrylic copolymer (A), exhibits high adhesion to low-polarity adherends such as olefins, and has high stress relaxation properties.
Additive (E)
The adhesive composition of the present invention may contain, in addition to the (meth) acrylic copolymer (a) and the rosin-based tackifying resin (B), if necessary, 1 or 2 or more additives such as a silane coupling agent, an antistatic agent, an antioxidant, a light stabilizer, a metal corrosion inhibitor, a plasticizer, a crosslinking accelerator, a surfactant, a (meth) acrylic copolymer other than the above (a), a reprocessing agent, and the like, within a range not to impair the effects of the present invention.
When the adhesive composition of the present invention contains other components, the amount of the other components is appropriately determined according to the type of the component, but is usually 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass, based on 100 parts by mass of the (meth) acrylic copolymer (a).
Organic solvent (F)
The adhesive composition of the present invention preferably contains an organic solvent (F) for adjusting the coatability thereof. The organic solvent (F) may be exemplified by the polymerization solvents described in column < (meth) acrylic copolymer (A) >. In the adhesive composition of the present invention, the content of the organic solvent is usually 20 to 90 mass%, preferably 30 to 90 mass%, relative to 100 mass% of the adhesive composition.
In the present specification, "solid content" refers to all components except the organic solvent (F) in the components contained in the adhesive composition, and "solid content concentration" refers to the proportion of the solid content to 100% by mass of the adhesive composition.
In the adhesive composition of the present invention, the amount of the (meth) acrylic copolymer (a) is usually 60 mass% or more, preferably 65 mass% or more, and more preferably 70 mass% or more, based on 100 mass% of the solid content. The upper limit of the total amount may be appropriately determined depending on the amounts of other components such as the rosin-based tackifying resin (B) and the crosslinking agent (C).
<Preparation of adhesive composition>
The pressure-sensitive adhesive composition of the present invention can be prepared, for example, by mixing the (meth) acrylic copolymer (a), the rosin-based tackifying resin (B), the crosslinking agent (C), and other components used as needed by a conventionally known method.
For example, the adhesive composition can be prepared by mixing and stirring the solution containing the (meth) acrylic copolymer (a) obtained in the synthesis of the (meth) acrylic copolymer (a), the rosin-based tackifying resin (B), the crosslinking agent (C) and other components used if necessary together or sequentially with a stirring device or the like. The stirring time is not particularly limited, but may be about 10 to 120 minutes at room temperature in view of operability and productivity.
[ marking sheet for road surface or floor surface ]]
<Marking sheet for road or groundStructure of the>
The marking sheet for road or floor of the present invention (hereinafter simply referred to as "marking sheet of the present invention") is characterized by having an adhesive layer formed from the adhesive composition of the present invention and a metal base material, and by laminating the adhesive layer and the metal base material.
A preferable structure of the marking sheet of the present invention includes a first adhesive layer, a first base material, a second adhesive layer, and a second base material, which are laminated in this order. The third pressure-sensitive adhesive layer, the third base material, the fourth pressure-sensitive adhesive layer, and the fourth base material may be further laminated on the second base material in this order, or a decorative layer, a protective layer, or the like may be further provided.
Fig. 1 is a schematic view showing a specific example of a layer structure of a marking sheet of the present invention. The label sheet shown in fig. 1 has a structure in which a first pressure-sensitive adhesive layer 11, a first base material 12 made of a metal base material, a second pressure-sensitive adhesive layer 13, a second base material 14 made of polyvinyl chloride, a third pressure-sensitive adhesive layer 15, and a third base material 16 made of polyimide are laminated in this order from an adherend or a release liner 10 in the thickness direction of the label sheet.
A release liner is usually provided on a surface to be adhered to a road surface or the like. When the marking sheet of the present invention is applied to a road surface or the like, the release liner is peeled off from the first adhesive layer, and the marking sheet is attached to a predetermined position on the road surface or the like via the first adhesive layer.
The respective layers will be described below with reference to fig. 1.
<Substrate material>
First substrate made of Metal substrate
The first substrate 12 made of a metal substrate used in the marking sheet of the present invention is preferably a metal foil in view of improving the following property to a road surface such as asphalt. The metal foil is not particularly limited, but from the viewpoints of price, availability, etc., aluminum foil, copper foil, iron foil, stainless steel foil are preferably used, and among these, aluminum foil that is easily deformed by hammering is preferably used.
The film thickness of the metal foil is preferably about 10 to 100. Mu.m, more preferably about 20 to 90. Mu.m. When the film thickness of the metal foil is within the above range, the metal foil is easily deformed and easily follows the irregularities of asphalt during construction such as hammering for adhesion to a road surface.
Second substrate
The second substrate 14 is a substrate for forming other layers such as a decorative layer and a protective layer, which will be described later.
The material of the second base material 14 is not particularly limited, and examples thereof include: plastic substrates, glass, woven fabrics, non-woven fabrics, papers, and the like. Examples of the plastic substrate include polyvinyl chloride (PVC), polycarbonate (PC), polymethyl methacrylate (PMMA), polyethylene terephthalate (PET), polyethylene (PE), polypropylene (PP), polyimide, acrylonitrile-butadiene-styrene copolymer (ABS), and polyamide (nylon). Among them, polyvinyl chloride, polyethylene terephthalate, polyethylene and polyimide are preferable from the viewpoint of easy printing of a desired color upon application of ink and easy industrial availability.
The film thickness of the second base material 14 is preferably about 30 to 300. Mu.m, more preferably about 50 to 250. Mu.m. The thickness of the second base material in the above range is a thickness that does not prevent pedestrians from walking, etc., and can exhibit a desired strength.
In addition, as the second base material 14, for example, a plurality of base materials may be laminated as in the third base material in fig. 1, and in this case, the plurality of base materials may be the same or different.
<Adhesive layer>
First adhesive layer
The first adhesive layer 11 is formed using the adhesive composition of the present invention described above. For example, the adhesive layer can be obtained by performing a crosslinking reaction in the adhesive composition, specifically by crosslinking the (meth) acrylic copolymer (a) with the crosslinking agent (C).
The conditions for forming the first adhesive layer 11 are as follows, for example. The pressure-sensitive adhesive composition of the present invention is applied to the release treated surface of the substrate or release liner, and the solvent is preferably removed by drying at 50 to 150 ℃, more preferably 60 to 100 ℃ for preferably 1 to 10 minutes, more preferably 2 to 7 minutes, although the type of solvent varies, to form a coating film. The film thickness of the dried coating film is preferably 5 to 125. Mu.m, more preferably 10 to 100. Mu.m.
The first adhesive layer 11 is preferably formed under the following conditions. The adhesive composition of the present invention is applied to the release treated surface of the substrate or release liner, and after the release liner is adhered to the coating film formed under the above conditions, the coating film is preferably cured at 23℃and 50% RH for 7 days or more, more preferably cured at 40℃for 3 to 5 days. Crosslinking under such curing conditions can form crosslinked products efficiently.
As a method of applying the adhesive composition, a method of applying a predetermined thickness by a known method such as spin coating, knife coating, roll coating, bar coating, doctor blade coating, die coating, gravure coating, and drying can be used.
Second adhesive layer
The second adhesive layer 13 may be formed of the same or different adhesive composition according to the present invention, or may be formed of other adhesive compositions. In the case where a plurality of substrates are further laminated after the second substrate 14, the adhesive composition for forming the adhesive layer for laminating the respective substrates may be the same or different.
The thickness of each adhesive layer is not particularly limited, but is preferably 5 to 125. Mu.m, more preferably 10 to 100. Mu.m.
Other layers
Other layers, such as other adhesive layers, decorative layers, metal layers, colored layers, printed layers, protective layers, and the like, may also be laminated on the second substrate 14 as needed.
The other layers may be formed of a single layer or a plurality of layers. The decorative layer is not necessarily formed on the entire surface of the second base material, and may be formed only in a predetermined region of the second base material.
The thickness of the other layer is not particularly limited, but is preferably about 30 to 300. Mu.m, and more preferably about 50 to 250. Mu.m. The film thickness of the other layer in the above range can exhibit a desired strength without impeding walking or the like of a pedestrian.
(decorative layer)
The decorative layer is a layer for giving a desired pattern, color, character, or the like to the pavement/floor marking sheet for marking a desired advertisement, guidance display, or the like.
The method of forming the decorative layer varies depending on the type of the decorative layer, but when the decorative layer is formed of an ink layer (print layer), for example, the decorative layer can be formed by relief printing such as flexography, gravure printing such as gravure printing, lithography such as offset printing, screen printing such as screen printing, printing by various printers such as an inkjet printer, or the like. In the case where the decorative layer is formed of a paint layer, the decorative layer may be formed by a coater such as a roll coater, a knife coater, a roll doctor coater, an air knife coater, a die coater, a bar coater, a gravure coater, a curtain coater, a spray coater, or a spray gun. In the case where the decorative layer is formed by transfer from a transfer sheet, the decorative layer may be formed by applying pressure to the transfer sheet laminated on the surface of the base material, or by heating the transfer sheet laminated on the surface of the base material, or the like, depending on the type of the transfer sheet. Further, in the case where the decorative layer is formed of a metal film, the decorative layer may be formed by vapor deposition, sputtering, or the like.
(protective layer)
The protective layer is formed by laminating a film of a polyester such as polyethylene terephthalate (PET), polyvinyl chloride, polyimide, polyurethane, acrylic resin, epoxy resin, fluororesin or the like directly or via a joining layer to a layer constituting the decorative laminate film, or may be formed by applying a resin composition to the surface of a film layer and drying.
<Release liner>
The release liner 10 for a marking sheet of the present invention is provided on the first adhesive layer 11 in the form of a marking sheet before being provided on a road surface or the like, for preventing the adhesive layer from adhering to a portion other than a desired surface to which the marking sheet of the present invention is to be adhered.
The release liner is not particularly limited, and a known release liner may be suitably used, and examples thereof include a release liner obtained by coating a resin film such as paper or polyester with a release agent.
The release agent is also related to the material of the pressure-sensitive adhesive layer, but a known release agent may be used, and examples thereof include silicone release agents and fluorine release agents.
Use of marking sheet for road surface or ground surface
The marking sheet of the present invention is excellent in adhesion, weather resistance, heat resistance, and moist heat resistance in addition to following up with a rough surface such as asphalt, and is therefore suitable for applications requiring these physical properties (for example, applications in which the marking sheet is used for applying a temporary mark to asphalt in a parking lot, road, or construction site used in a car, a large truck, or the like, or applications in which the marking sheet is temporarily stuck to a floor surface where there are many pedestrians in the interior and exterior, because it is difficult for the adhesive to transfer from the base material to the adherend at the time of peeling).
Examples
The present invention will be specifically described based on examples, but the present invention is not limited to these examples. In the following description of examples and the like, "parts" means "parts by mass" unless otherwise specified.
The physical properties were measured as follows.
[ ratio of component having molecular weight of 5000 or less in the (meth) acrylic copolymer having weight average molecular weight (Mw) and number average molecular weight (Mn) ]
The (meth) acrylic copolymer of synthesis example and the like was subjected to Gel Permeation Chromatography (GPC) to obtain a differential molecular weight distribution curve and an integral molecular weight curve under the following conditions. Mw and Mw/Mn are determined from the differential molecular weight distribution curve, and the proportion of a component having a molecular weight of 5000 or less is determined from the integral molecular weight distribution curve.
Measurement device: HLC-8120GPC (manufactured by Tosoh Co., ltd.)
GPC column composition: the following 5 columns were connected (all manufactured by Tosoh Co., ltd.)
(1) TSKgel HxL-H (protective column)
(2)TSKgel G7000HXL
(3)TSKgel GMHxL
(4)TSKgel GMHxL
(5)TSKgel G2500HXL
Flow rate: 1.0mL/min
Column temperature: 40 DEG C
Sample concentration: 1.5% (w/v) (diluted with tetrahydrofuran)
Mobile phase solvent: tetrahydrofuran (THF)
Standard polystyrene conversion
Synthesis example A-1
Into a flask equipped with a stirring device, a nitrogen inlet, a thermometer and a reflux condenser, 40.5 parts of n-Butyl Acrylate (BA), 56 parts of 2-ethylhexyl acrylate (2 EHA), 3.5 parts of Acrylic Acid (AA) and 100 parts of ethyl acetate were charged, and the contents of the flask were heated to 70℃while introducing nitrogen into the flask. Then, 0.05 part of 2,2' -azobisisobutyronitrile (hereinafter also referred to as "AIBN") was added to the flask with stirring. Heating and cooling for 5 hours to enable the temperature of the contents of the flask to be maintained at 70 ℃. After the temperature was raised to 78 ℃, the reflux reaction was carried out for 2 hours to obtain (meth) acrylic copolymer (A-1). After the completion of the reaction, the mixture was diluted with ethyl acetate to prepare a polymer solution containing the (meth) acrylic copolymer (A-1) at a solid content concentration of 30% by mass. The Mw of the obtained (A-1) was 89 ten thousand as measured by GPC, the Mw/Mn was 5.2, and the proportion of the component having a molecular weight of 5000 or less was 0.1 mass%.
Synthesis examples A-2 to A-10
(meth) acrylic copolymers (A-2) to (A-10) were produced in the same manner as in Synthesis example A-1, except that the raw materials shown in Table 1 were used.
Synthesis example A-11
Into a flask equipped with a stirring device, a nitrogen inlet, a thermometer and a reflux condenser, 40.5 parts of n-Butyl Acrylate (BA), 56 parts of 2-ethylhexyl acrylate (2 EHA), 3.5 parts of Acrylic Acid (AA) and 140 parts of ethyl acetate were charged, and the contents of the flask were heated to 70℃while introducing nitrogen into the flask. Then, 0.05 part of AIBN was added to the flask with stirring. Heating and cooling for 5 hours to enable the temperature of the contents of the flask to be maintained at 70 ℃. During this period, 0.05 part of AIBN was added 10 minutes after the start of the reaction, 0.05 part of AIBN was added 20 minutes after the start of the reaction, and 0.05 part of AIBN was added 30 minutes after the start of the reaction. Then, the temperature was raised to 78℃and the reflux reaction was carried out for 2 hours to obtain (meth) acrylic copolymer (A-11). After the completion of the reaction, the mixture was diluted with ethyl acetate to obtain a polymer solution containing (meth) acrylic copolymer (A-11) at a solid content concentration of 30% by mass. The Mw of the obtained (A-11) was 42 million, the Mw/Mn was 9.0, and the ratio of components having a molecular weight of 5000 or less was 1.7 mass% as measured by GPC.
TABLE 1
The symbols of the monomer components in Table 1 are as follows.
BA: acrylic acid n-butyl ester
t-BA: acrylic acid tert-butyl ester
2EHA: 2-ethylhexyl acrylate
i-OA: isooctyl acrylate
AA: acrylic acid
Example 1
The polymer solution obtained in Synthesis example A-1 (solid content: 30 mass%), DP-2669 (Ha Lima, manufactured by Kagaku Co., ltd., softening point: 135 ℃ C.) as a tackifying resin, and L-45K (manufactured by Zoo chemical Co., ltd., isocyanate crosslinking agent, solid content: 45 mass%) as a crosslinking agent were mixed in amounts such that the solid content ratio was 100 parts of A-1, 20 parts of DP-2669, and 1.5 parts of L-45K, respectively, to obtain an adhesive composition.
Examples 2 to 9 and comparative examples 1 to 10
An adhesive composition was prepared in the same manner as in example 1, except that the mixing composition of the adhesive composition was changed to that described in table 2 or table 3. The numerical values in the component columns in tables 3 and 4 represent parts by mass.
[ production of marking sheet ]]
A first adhesive layer having a thickness of 30 μm after drying was formed on a liner subjected to a peeling treatment using the obtained adhesive composition, an aluminum substrate (50 μm thick) as a first base material was formed thereon, an adhesive layer having a thickness of 50 μm after drying was formed thereon using the same adhesive composition as the first adhesive as a second adhesive, and a PVC substrate (50 μm thick) as a second base material was further laminated thereon, whereby a marking sheet for production evaluation was produced.
[ evaluation method ]
The heat resistance, (2) the wet heat resistance, (3) the adhesion to a metal substrate, (4) the peeling resistance evaluation based on the road surface adhesion test, (5) the re-peeling property evaluation after the road surface adhesion test, and (6) the adhesion force evaluation were performed. The respective evaluation methods are as follows. The evaluation results are shown in tables 2 and 3.
(1) Evaluation of Heat resistance
The label sheet was attached to SUS and polished at 80 ℃ for 7 days, and then allowed to stand at 23 ℃/50% rh for 30 minutes, and then visually observed to peel from the surface of the adherend at a peeling angle of 180 ° and a stretching speed of 300 mm/min, and evaluated according to the following criteria.
(evaluation criterion)
O: the adhesive has a transfer area of less than 1%.
Delta: the adhesive has a transfer area of 1% or more and less than 20%.
X: the adhesive has a transfer area of 20% or more.
(2) Evaluation of moisture resistance
The label sheet was attached to the polished SUS, allowed to stand at 60 ℃/95% rh for 7 days, and then allowed to stand at 23 ℃/50% rh for 30 minutes, and then visually observed for peeling from the surface of the adherend at a peeling angle of 180 ° and a stretching speed of 300 mm/min, and evaluated according to the following criteria.
(evaluation criterion)
O: the adhesive has a transfer area of less than 1%.
Delta: the adhesive has a transfer area of 1% or more and less than 20%.
X: the adhesive has a transfer area of 20% or more.
(3) Evaluation of adhesion to Metal substrate
The adhesive layer portion was rubbed with a finger and visually observed, and evaluated according to the following criteria.
(evaluation criterion)
O: the finger was rubbed 30 times or more without any change such as peeling.
Delta: peeling was generated after wiping the finger 11 to 30 times.
X: peeling occurred within 10 finger rubs.
(4) Peel resistance evaluation based on road surface adhesion test
After the asphalt pavement is cleaned, a marking sheet cut into a size of 10cm×15cm is stuck to the pavement by hand, and then compacted by a rubber hammer. The peeling state of the label sheet after 3 months was visually observed, and evaluated according to the following criteria.
(evaluation criterion)
O: no peeling at all.
Delta: peeling or tilting of the ends was observed.
X: stripping.
(5) Evaluation of Repeal Property after pavement adhesion test
After the asphalt pavement is cleaned, a marking sheet cut into a size of 10cm×15cm is stuck to the pavement by hand, and then compacted by a rubber hammer. The peeling state of the label sheet after peeling for 3 months was visually observed and evaluated according to the following criteria.
(evaluation criterion)
O: the adhesive has a transfer area of less than 1%.
Delta: the adhesive has a transfer area of 1% or more and less than 20%.
X: the adhesive has a transfer area of 20% or more.
(6) Evaluation of adhesion
The label sheet was attached to the polished SUS, and after leaving it to stand at 23℃and 50% RH for 20 minutes, the adhesive force (N/25 mm) at a peeling angle of 180℃and a stretching speed of 300 mm/min from the surface of the adherend was evaluated.
TABLE 2
TABLE 3 Table 3
The tackifying resins in tables 2 and 3 are detailed below.
DP-2669 (HARITACK DP-2669 manufactured by Ha Lima Chemie Co., ltd.; rosin-based tackifying resin, softening point 135 ℃ C.)
D-135 (PENSEL D-135 manufactured by Deskachi chemical Co., ltd.; rosin-based tackifying resin, softening point 135 ℃ C.)
D-160 (PENSEL D-160 manufactured by Deskachi chemical industry Co., ltd.; rosin-based tackifying resin, softening point 160 ℃ C.)
FTR-6100 (Sanjing chemical Co., ltd.; styrene-based tackifying resin, softening point 100 ℃ C.)
D-125 (PENSEL D-125 manufactured by Deskachi chemical industry Co., ltd.; rosin-based tackifying resin, softening point 125 ℃ C.)
SEA-100 (SUPER ESTER A-100 manufactured by Deskaching chemical Co., ltd.; rosin-based tackifying resin, softening point 100 ℃ C.)
L-45K (from Hold chemical Co., ltd.; isocyanate crosslinking agent)
As is clear from table 2, the marking sheets obtained in examples 1 to 9 were excellent in stress relaxation property under high-temperature and high-humidity environments while maintaining adhesion to a base material and adhesion to a road surface, which are required as adhesive properties, and further, less in adhesive residue to a road surface when peeled from a road surface, that is, excellent in re-peelability to a road surface.
The results of poor adhesive properties were obtained for the marking sheets of comparative examples 1 and 2 using a rosin-based tackifying resin having a softening point of less than 120 ℃, the marking sheets of comparative examples 3 to 5 having a softening point of 120 ℃ or higher, the marking sheets of comparative examples 6 to 9 having a content of each monomer out of the range specified in the present invention, and the marking sheet of comparative example 10 having a ratio of components having a molecular weight of 5000 or less in the (meth) acrylic copolymer (a) out of the range specified in the present invention.
Symbol description
10: adherend or release liner
11: first adhesive layer
12: first substrate composed of metal substrate
13: second adhesive layer
14: a second substrate made of polyvinyl chloride
15: third adhesive layer
16: a third substrate composed of polyimide.
Claims (7)
1. A pavement or floor adhesive composition comprising a (meth) acrylic copolymer (A) and a rosin-based tackifying resin (B),
the (meth) acrylic copolymer (A) is a copolymer comprising 20 to 69 mass% of a (meth) acrylic acid alkyl ester monomer (a 1) having 1 to 7 alkyl carbon atoms, 30 to 74 mass% of a (meth) acrylic acid alkyl ester monomer (a 2) having 8 to 20 alkyl carbon atoms, and 1 to 6 mass% of a monomer component containing an acid group monomer (a 3), wherein the total of the components (a 1) to (a 3) is 100 mass%,
the content of the rosin-based tackifying resin (B) is 10 to 30 parts by mass per 100 parts by mass of the (meth) acrylic copolymer (A),
the ratio of the component having a molecular weight of 5000 or less in the (meth) acrylic copolymer (A) is 1.5% by mass or less.
2. The adhesive composition for road surfaces or floors as claimed in claim 1, wherein the softening point of the rosin-based tackifying resin is 120 ℃ or higher.
3. The adhesive composition for road surfaces or floors as claimed in claim 1 or 2, further comprising a crosslinking agent (C).
4. A pavement or floor marking sheet comprising an adhesive layer formed from the adhesive composition according to any one of claims 1 to 3 and a metal base material.
5. The pavement or ground marking sheet according to claim 4, wherein the metal base material is aluminum foil.
6. The pavement or ground marking sheet according to claim 4 or 5, further comprising a plastic base material.
7. The pavement or floor marking sheet according to claim 6, wherein the plastic substrate is at least one substrate selected from the group consisting of polyvinyl chloride, polyethylene terephthalate, polyethylene and polyimide.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2020168434 | 2020-10-05 | ||
| JP2020-168434 | 2020-10-05 | ||
| PCT/JP2021/035832 WO2022075143A1 (en) | 2020-10-05 | 2021-09-29 | Pressure-sensitive adhesive composition for road surface or floor surface and marking sheet |
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| CN116368198A true CN116368198A (en) | 2023-06-30 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015184488A (en) * | 2014-03-24 | 2015-10-22 | リンテック株式会社 | Road surface/floor surface marking laminate sheet and road surface/floor surface marking sheet |
| CN105102572A (en) * | 2013-04-02 | 2015-11-25 | 东友精细化工有限公司 | Adhesive composition |
| CN108690536A (en) * | 2017-04-07 | 2018-10-23 | 综研化学株式会社 | Adhesive composition and bonding sheet |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5286460B2 (en) * | 2007-08-01 | 2013-09-11 | ブリヂストン化成品株式会社 | Sleeve hole filling adhesive sheet |
| JP6893156B2 (en) * | 2017-09-29 | 2021-06-23 | 積水化学工業株式会社 | Double-sided adhesive tape |
| JP7275650B2 (en) * | 2018-03-02 | 2023-05-18 | 三菱ケミカル株式会社 | Adhesive composition for difficult-to-adhere adherends, adhesive for difficult-to-adhere adherends, and adhesive tape for difficult-to-adhere adherends |
| EP3943294A4 (en) * | 2019-03-18 | 2022-12-07 | Sekisui Chemical Co., Ltd. | Composite structure and double-sided adhesive tape |
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2021
- 2021-09-29 CN CN202180064969.3A patent/CN116368198A/en active Pending
- 2021-09-29 WO PCT/JP2021/035832 patent/WO2022075143A1/en active Application Filing
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105102572A (en) * | 2013-04-02 | 2015-11-25 | 东友精细化工有限公司 | Adhesive composition |
| JP2015184488A (en) * | 2014-03-24 | 2015-10-22 | リンテック株式会社 | Road surface/floor surface marking laminate sheet and road surface/floor surface marking sheet |
| CN108690536A (en) * | 2017-04-07 | 2018-10-23 | 综研化学株式会社 | Adhesive composition and bonding sheet |
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