CN114574109B - UV (ultraviolet) photo-curing pressure-sensitive adhesive and application thereof - Google Patents
UV (ultraviolet) photo-curing pressure-sensitive adhesive and application thereof Download PDFInfo
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- CN114574109B CN114574109B CN202011387874.9A CN202011387874A CN114574109B CN 114574109 B CN114574109 B CN 114574109B CN 202011387874 A CN202011387874 A CN 202011387874A CN 114574109 B CN114574109 B CN 114574109B
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- acrylate
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- methacrylate
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- sensitive adhesive
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 51
- 238000000016 photochemical curing Methods 0.000 title abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 15
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 32
- 238000012662 bulk polymerization Methods 0.000 claims description 28
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 17
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229920006222 acrylic ester polymer Polymers 0.000 claims description 14
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 8
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 8
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 7
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 238000003848 UV Light-Curing Methods 0.000 claims description 5
- 239000012986 chain transfer agent Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 4
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 4
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 4
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 4
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 229920002799 BoPET Polymers 0.000 claims description 3
- 238000001723 curing Methods 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 2
- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 1
- YWTAAYBDIQFCLL-UHFFFAOYSA-N n-ethenylcyclohexanecarboxamide Chemical compound C=CNC(=O)C1CCCCC1 YWTAAYBDIQFCLL-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 9
- 230000007613 environmental effect Effects 0.000 abstract description 7
- 229920000642 polymer Polymers 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 10
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 8
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000012512 characterization method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229920000178 Acrylic resin Polymers 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- -1 acrylic ester Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- XHGOVHOCQHSNTI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy formate Chemical compound CC(C)(C)OOC=O XHGOVHOCQHSNTI-UHFFFAOYSA-N 0.000 description 1
- UXKQGJYFPNFUJY-UHFFFAOYSA-N 1-(2-methylbutan-2-yldiazenyl)cyclohexane-1-carbonitrile Chemical compound CCC(C)(C)N=NC1(C#N)CCCCC1 UXKQGJYFPNFUJY-UHFFFAOYSA-N 0.000 description 1
- QKNQPCLQRXMWJO-UHFFFAOYSA-N 1-(tert-butyldiazenyl)cyclohexane-1-carbonitrile Chemical compound CC(C)(C)N=NC1(C#N)CCCCC1 QKNQPCLQRXMWJO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The invention discloses a UV (ultraviolet) photo-curing pressure-sensitive adhesive and application thereof, wherein the UV photo-curing pressure-sensitive adhesive is prepared by directly and fully mixing the following components at normal temperature according to the following proportion: 10-60 parts by mass of acrylate polymer containing active double bonds, 10-60 parts by mass of monofunctional acrylate soft monomer, 0-20 parts by mass of monofunctional acrylate hard monomer, 0-10 parts by mass of multifunctional acrylate monomer containing at least two polymerizable double bonds per molecule, 0-10 parts by mass of acrylate functional monomer and 0.5-10 parts by mass of UV photoinitiator, wherein the sum of the parts by mass of the components is 100. The UV photo-curing pressure-sensitive adhesive disclosed by the invention has the advantages of no solvent pollution in the preparation and use processes, capability of meeting the environmental protection requirement, low viscosity, easiness in uniform coating, convenience in coating operation, excellent bonding performance, peeling strength, convenience in use, low preparation cost and easiness in realization of large scale.
Description
Technical Field
The invention relates to a UV (ultraviolet) photo-curing pressure-sensitive adhesive and application thereof, belonging to the technical field of functional materials.
Background
Currently, there are reports in the art on UV photo-curable pressure-sensitive adhesives, such as: CN108300332A discloses a photo-curing pressure-sensitive adhesive, which comprises 65-80 parts of soft monomer, 10-20 parts of hard monomer, 5-15 parts of polar monomer and 0.1-9 parts of auxiliary initiation monomer containing tertiary amine group; 0.5 to 1.5 parts of initiator, 100 parts of solvent and 50 to 100 parts of reactive diluent, wherein the pressure-sensitive adhesive has no volatilization problem of organic solvent and small molecular photoinitiator in use, has lower viscosity (516 to 618 cps) and better adhesive property (holding viscosity for 6 to 9 hours; peel strength 1143 to 1896gf/25 mm) at 40 ℃, but has environmental protection problem caused by evaporation of a large amount of solvent in preparation; in addition, CN108192537A also discloses an ultraviolet curing pressure-sensitive adhesive, which comprises the following components in parts by weight: 75-90 parts of acrylic ester monomer or methacrylic ester monomer containing alkyl, 2-5 parts of copolymerizable monomer containing hydroxyl, 1-3 parts of copolymerizable monomer containing carboxyl, 1-5 parts of acrylic ester comonomer or methacrylic ester comonomer containing cinnamon group, 0.2 part of active initiator and 50-80 parts of solvent, wherein the adhesive can realize good photocuring property under the condition of no photoinitiator, but the pressure-sensitive adhesive has peel strength of only 70-150gf/25mm (equivalent to 0.68-1.47N/25 mm), and contains a large amount of solvent, the solid content of only 45 percent, and the solvent needs to be completely volatilized in use, so that the pressure-sensitive adhesive has the environmental protection problem in use.
Along with the increasing environmental awareness and the implementation of the strategy of sustainable development of human beings, the field is urgently needed to develop a UV photo-curing pressure-sensitive adhesive which has the advantages of no solvent pollution in the preparation and use processes, capability of meeting the environmental protection requirement, low viscosity, easy and uniform coating, excellent bonding performance, peeling strength, convenient use and low preparation cost.
Disclosure of Invention
Aiming at the problems and the demands of the prior art, the invention aims to provide the UV light-cured pressure-sensitive adhesive which has no solvent pollution in the preparation and use processes, can meet the environmental protection requirement, has lower viscosity, is easy to uniformly coat, has excellent bonding performance and peeling strength, is convenient to use and has low preparation cost, and the application thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a UV photo-curing pressure-sensitive adhesive is prepared by directly and fully mixing the following components at normal temperature:
the sum of the mass parts of the components is 100.
The UV light curing pressure-sensitive adhesive is prepared by directly and fully mixing the following components at normal temperature according to the following proportion:
the sum of the mass parts of the components is 100.
Further preferably, the UV light curing pressure-sensitive adhesive is prepared by directly and fully mixing the following components at normal temperature according to the following proportion:
the sum of the mass parts of the components is 100.
In a preferred embodiment, the acrylic polymer containing an active double bond has a weight average molecular weight of 20000 ～ 1000000, a number average molecular weight of 10000 to 500000, a glass transition temperature of-100 to 0℃and a double bond density of 0.005 to 0.5mol/kg.
Further preferably, the weight average molecular weight of the acrylic polymer containing an active double bond is in the range of 50000 to 100000, the number average molecular weight of the acrylic polymer is in the range of 25000 to 50000, the glass transition temperature of the acrylic polymer is in the range of-55 ℃ to-15 ℃, and the double bond density of the acrylic polymer is in the range of 0.01 to 0.1mol/kg.
In a preferred embodiment, the acrylate polymer containing an active double bond is obtained by bulk polymerization of 100 parts by mass of a monofunctional monomer having one polymerizable double bond per molecule, 0.1 to 10 parts by mass of a difunctional monomer having two polymerizable double bonds per molecule, 0.1 to 1.0 parts by mass of an initiator and 1 to 5 parts by mass of a chain transfer agent under heating in a constant temperature water bath at 40 to 70 ℃.
Further preferably, the acrylate polymer containing an active double bond is obtained by bulk polymerization of 100 parts by mass of a monofunctional monomer having one polymerizable double bond per molecule, 0.5 to 5 parts by mass of a difunctional monomer having two polymerizable double bonds per molecule, 0.1 to 1 part by mass of an initiator and 1 to 5 parts by mass of a chain transfer agent under heating in a constant temperature water bath at 50 to 60 ℃.
Further preferred is that the monofunctional monomer having one polymerizable double bond per molecule is selected from any one or more of methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, t-butyl methacrylate, isooctyl methacrylate, isobornyl methacrylate, lauryl methacrylate, methacrylic acid, acrylic acid, ethyl acrylate, methyl acrylate, butyl acrylate, isooctyl acrylate, lauryl acrylate, styrene.
Further preferred is that the difunctional monomer having two polymerizable double bonds per molecule is selected from any one or more of ethylene glycol diacrylate, hexylene glycol diacrylate, tripropylene glycol diacrylate, butylene glycol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate, allyl acrylate.
Further preferred is an initiator selected from any one or more of azobisisobutyronitrile, 1-t-pentylazo-1-cyanocyclohexane, lauroyl peroxide, 1-t-butylazo-1-cyanocyclohexane, t-butylperoctoate, t-butylperoxy-2-ethylhexanoate, t-butylperbenzoate, t-butylperoxyformate, di-t-butylperoxide, dicumyl hydroperoxide, t-amyl hydroperoxide, t-butyl hydroperoxide.
Further preferred, the chain transfer agent is selected from any one or a combination of more than one of n-propyl mercaptan, n-butyl mercaptan, n-octyl mercaptan, n-dodecyl mercaptan, dithioesters and alpha-methyl styrene dimer.
Further preferred is the combination of methyl methacrylate, n-butyl acrylate and isooctyl acrylate as the monofunctional monomer having one polymerizable double bond per molecule, tripropylene glycol diacrylate or dipropylene glycol diacrylate as the difunctional monomer having two polymerizable double bonds per molecule, lauroyl peroxide as the initiator, and n-dodecyl mercaptan as the chain transfer agent.
Preferably, the monofunctional acrylate soft monomer is selected from any one or more of n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, isooctyl acrylate, lauryl acrylate, stearyl acrylate, isooctyl methacrylate, lauryl methacrylate, stearyl methacrylate and 2-ethyl hexyl acrylate.
In a preferred embodiment, the monofunctional acrylate hard monomer is selected from any one or more of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobornyl methacrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate, t-butyl acrylate and styrene.
Preferably, the multifunctional acrylate monomer containing at least two polymerizable double bonds per molecule is selected from any one or more of ethylene glycol diacrylate, hexyl glycol diacrylate, tripropylene glycol diacrylate, butylene glycol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate, allyl acrylate, trimethylolpropane triacrylate, and trimethylolpropane trimethacrylate.
In a preferred embodiment, the acrylate functional monomer is selected from any one or more of acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylamide, N-vinylcyclohexane amide, maleic anhydride, and glycidyl methacrylate.
In a preferred embodiment, the UV photoinitiator is selected from any one or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, benzophenone, benzil dimethyl ether, benzoin dimethyl ether and benzoin isopropyl ether.
The application of the UV light-cured pressure-sensitive adhesive is that the UV light-cured pressure-sensitive adhesive is coated on a substrate film through a film coater, and then the substrate film is placed under an ultraviolet irradiation device for light curing to prepare the pressure-sensitive adhesive product.
One embodiment is to coat the UV light curing pressure sensitive adhesive on a PET film by a 50 μm film coater, and then to make one-time irradiation on a conveyor belt type UV machine at a conveying speed of 0.1m/s and an irradiation power of 2000W to prepare the pressure sensitive adhesive product.
Compared with the prior art, the invention has the following beneficial effects:
1) The UV light-cured pressure-sensitive adhesive can be prepared by directly and fully mixing the components according to the proportion at normal temperature, and is simple in preparation process, environment-friendly, energy-saving and easy to realize scale;
2) The detection shows that: the viscosity of the UV light-cured pressure-sensitive adhesive is only 400-800 cps at 20 ℃, so that the UV light-cured pressure-sensitive adhesive is very favorable for uniform coating and convenient coating operation, and has important significance for high-quality preparation of pressure-sensitive adhesive products;
3) The UV light curing pressure-sensitive adhesive is very convenient to prepare pressure-sensitive adhesive products, and only needs to carry out one-time illumination at a conveying speed of 0.1m/s and an illumination power of 2000W, thereby being environment-friendly, energy-saving and easy to realize scale;
4) The comparison experiment can also show that: compared with the comparison situation that acrylate saturated polymer is adopted as a polymer component under the same condition, the viscosity of the obtained UV light-cured pressure-sensitive adhesive can be reduced to 43% under the same condition, the holding power is improved by 3 times, the stripping force is improved by 1.5 times, and unexpected excellent adhesive property is generated;
5) The acrylate polymer containing the active double bond can be obtained by bulk polymerization at a lower water bath temperature, so that the preparation process is simple, energy-saving and environment-friendly, and industrialization is facilitated;
In a word, the invention creatively adopts the acrylate polymer containing active double bonds as the polymer component of the UV photo-curing pressure-sensitive adhesive, so that the obtained UV photo-curing pressure-sensitive adhesive has no solvent pollution in the preparation and use processes, can meet the environmental protection requirement, has low viscosity, is easy to uniformly coat and convenient to coat and operate, has excellent adhesive property and peeling strength, is convenient to use, has low preparation cost and is easy to realize scale, and compared with the prior art, the invention not only has remarkable progress, but also has unexpected technical effect.
Detailed Description
The technical scheme of the invention is further and fully described in the following by combining examples and comparative examples.
In the following examples and comparative examples:
Initial tack: the measurement was carried out by using a primary tackiness measuring instrument according to the standard of the pressure-sensitive adhesive tape primary tackiness test method (ball method) (GB/T4852-2002).
Holding viscosity: the measurement was carried out by using a holding-viscosity tester according to the standard of the holding-viscosity test method for pressure-sensitive adhesive tapes (GB/T4851-1988).
180 ° Peel strength: the measurement was carried out by using a peel tester according to the standard of test method for adhesive tape peel strength (GB/T2792-2014).
Viscosity: the temperature was measured by a Brookfield rotational viscometer and was 20 ℃.
Double bond density: the molar number (mol/kg) of double bonds contained in the polymer per unit weight can be calculated through the peak area ratio of the double bond hydrogen peak to the main chain hydrogen peak of the polymer in the nuclear magnetic hydrogen spectrum of the polymer.
Example 1: preparation of acrylate polymers containing reactive double bonds
240 G of MMA (methyl methacrylate), 180 g of BMA (n-butyl methacrylate), 90g of EHA (isooctyl acrylate), 72 g of BA (n-butyl acrylate), 18 g of TPGDA (tripropylene glycol diacrylate), 3g of lauroyl peroxide and 21 g of n-dodecyl mercaptan are added into a bulk polymerization bag, stirred and uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out under the heating of a constant-temperature water bath at 55 ℃ for 10 hours, then the bulk polymerization bag is taken out, the cooling is carried out to room temperature, and the obtained solid acrylic resin is crushed to obtain the acrylate polymer containing active double bonds, which is simply referred to as a polymer I, and characterization data of the polymer are shown in a table 1.
Comparative example 1: preparation of saturated acrylate polymers
210 G of MMA (methyl methacrylate), 120 g of BMA (n-butyl methacrylate), 150 g of EHA (isooctyl acrylate), 120 g of BA (n-butyl acrylate), 3g of lauroyl peroxide and 15 g of n-dodecyl mercaptan are added into a bulk polymerization bag, the mixture is stirred and uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out for 10 hours under the heating of the constant-temperature water bath at 55 ℃, then the bulk polymerization bag is taken out, the mixture is cooled to room temperature, the obtained solid acrylic resin is crushed to obtain the saturated acrylic ester polymer, the saturated acrylic ester polymer is abbreviated as a polymer Ia, and characterization data of the polymer are shown in a table 1.
Example 2: preparation of acrylate polymers containing reactive double bonds
180 G of MMA (methyl methacrylate), 120 g of BMA (n-butyl methacrylate), 180 g of EHA (isooctyl acrylate), 111 g of BA (n-butyl acrylate), 3g of TPGDA (tripropylene glycol diacrylate), 3g of lauroyl peroxide and 15 g of n-dodecyl mercaptan are added into a bulk polymerization bag, the mixture is stirred to be uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out for 10 hours under the heating of a constant-temperature water bath at 55 ℃, then the bulk polymerization bag is taken out, the cooling is carried out to room temperature, and the obtained solid acrylic resin is crushed to obtain the acrylate polymer containing active double bonds, which is simply referred to as a polymer II, and characterization data of the polymer are shown in a table 1.
Comparative example 2: preparation of saturated acrylate polymers
120 G of MMA (methyl methacrylate), 60 g of BMA (n-butyl methacrylate), 240 g of EHA (isooctyl acrylate), 180 g of BA (n-butyl acrylate), 3g of lauroyl peroxide and 11 g of n-dodecyl mercaptan are added into a bulk polymerization bag, the mixture is stirred and uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out for 10 hours under the heating of the constant-temperature water bath at 55 ℃, the bulk polymerization bag is taken out and cooled to room temperature, the obtained solid acrylic resin is crushed to obtain the saturated acrylic ester polymer, the saturated acrylic ester polymer is abbreviated as a polymer IIa, and characterization data of the polymer are shown in a table 1.
Example 3: preparation of acrylate polymers containing reactive double bonds
180 G of MMA (methyl methacrylate), 114 g of BMA (n-butyl methacrylate), 186 g of EHA (isooctyl acrylate), 114 g of BA (n-butyl acrylate), 5g of DPGDA (dipropylene glycol diacrylate), 3g of lauroyl peroxide and 9 g of n-dodecyl mercaptan are added into a bulk polymerization bag, the mixture is stirred to be uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out for 10 hours under the heating of a constant-temperature water bath at 55 ℃, then the bulk polymerization bag is taken out, the cooling is carried out to room temperature, and the obtained solid acrylic resin is crushed to obtain the acrylate polymer containing active double bonds, which is simply referred to as a polymer III, and characterization data of the polymer are shown in a table 1.
Comparative example 3: preparation of saturated acrylate polymers
108 G of MMA (methyl methacrylate), 48 g of BMA (n-butyl methacrylate), 252 g of EHA (isooctyl acrylate), 192 g of BA (n-butyl acrylate), 3g of lauroyl peroxide and 5.5 g of n-dodecyl mercaptan are added into a bulk polymerization bag, the mixture is stirred to be uniformly mixed, the bulk polymerization bag is placed into a water bath, the bulk polymerization is carried out for 10 hours under the heating of the constant-temperature water bath at 55 ℃, the bulk polymerization bag is taken out, the mixture is cooled to room temperature, the obtained solid acrylic resin is crushed to obtain the saturated acrylic ester polymer, the saturated acrylic ester polymer is abbreviated as a polymer IIIa, and characterization data of the polymer are shown in a table 1.
Table 1 characterization data for the polymers obtained in the examples and comparative examples
Application examples and application comparative examples
The acrylate polymer containing active double bond prepared in the examples 1-3 and the saturated acrylate polymer prepared in the comparative examples 1-3 are directly and fully mixed at normal temperature according to the components and the proportions shown in the table 2 to obtain the UV light-cured pressure-sensitive adhesive and the comparative pressure-sensitive adhesive, and the viscosity test is carried out, wherein the test results are shown in the table 2; then, the pressure-sensitive adhesive was coated on a PET film by using a 50 μm film coater, and then, the film was put on a conveyor type UV machine (for example, FUMAX 9400D type UV machine manufactured by Kunsfield electronic technology Co., ltd.) and irradiated with light at a conveying speed of 0.1m/s and an irradiation power of 2000W for one time to prepare a pressure-sensitive adhesive article, and then, initial adhesion, holding adhesion and peeling force were measured, and the test results are shown in Table 2.
Table 2 formulation and performance test results of application examples and application comparative examples
As can be seen from table 2: compared with the comparison situation that the acrylate polymer containing active double bonds is adopted as the polymer component of the UV photo-curing pressure-sensitive adhesive under the same condition, the viscosity of the obtained UV photo-curing pressure-sensitive adhesive can be reduced to 43 percent under the same condition, the holding power is improved by 3 times, the stripping force is improved by 1.5 times, the coating uniformity is very favorable, the coating operation is convenient, the high-quality preparation of pressure-sensitive adhesive products is of great significance, and the unexpected excellent adhesive property is generated.
Finally, it is pointed out here that: the above is only a part of the preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention, and some insubstantial modifications and adaptations of the present invention based on the foregoing are within the scope of the present invention.
Claims (8)
1. The UV light-cured pressure-sensitive adhesive is prepared by directly and fully mixing the following components at normal temperature according to the following proportion:
30-50 parts by mass of an acrylate polymer containing active double bonds;
30-50 parts by mass of monofunctional acrylate soft monomer;
5-20 parts by mass of a monofunctional acrylate hard monomer;
1-5 parts by mass of a multifunctional acrylate monomer containing at least two polymerizable double bonds per molecule;
1-5 parts by mass of functional monomer;
1-5 parts by mass of UV photoinitiator;
The sum of the mass parts of the components is 100;
the weight average molecular weight of the acrylic ester polymer containing active double bonds is 20000 ～ 1000000, the number average molecular weight of the acrylic ester polymer is 10000-500000, the glass transition temperature of the acrylic ester polymer is minus 100-0 ℃, and the double bond density of the acrylic ester polymer is 0.005-0.5 mol/kg; the method is characterized in that:
The acrylate polymer containing active double bonds is prepared by performing bulk polymerization of 100 parts by mass of monofunctional monomer with one polymerizable double bond per molecule, 0.1-10 parts by mass of difunctional monomer with two polymerizable double bonds per molecule, 0.1-1.0 parts by mass of initiator and 1-5 parts by mass of chain transfer agent under the heating of constant-temperature water bath at 40-70 ℃; the monofunctional monomer with one polymerizable double bond per molecule is selected from any one or a combination of a plurality of methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, isooctyl methacrylate, isobornyl methacrylate, lauryl methacrylate, methacrylic acid, acrylic acid, ethyl acrylate, methyl acrylate, butyl acrylate, isooctyl acrylate, lauryl acrylate and styrene; the difunctional monomer with two polymerizable double bonds per molecule is selected from any one or a combination of a plurality of ethylene glycol diacrylate, hexanediol diacrylate, tripropylene glycol diacrylate, butanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate and allyl acrylate; the functional monomer is selected from any one or a combination of a plurality of acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylamide, N-vinyl cyclohexanamide, maleic anhydride and glycidyl methacrylate.
2. The UV light curable pressure sensitive adhesive of claim 1, wherein: the weight average molecular weight of the acrylic ester polymer containing active double bonds is 50000-100000, the number average molecular weight of the acrylic ester polymer is 25000-50000, the glass transition temperature of the acrylic ester polymer is minus 55 ℃ to minus 15 ℃, and the double bond density of the acrylic ester polymer is 0.01-0.1 mol/kg.
3. The UV light curable pressure sensitive adhesive of claim 1, wherein: the monofunctional acrylate soft monomer is selected from any one or a combination of a plurality of n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, isooctyl acrylate, lauryl acrylate, stearyl acrylate, isooctyl methacrylate, lauryl methacrylate and stearyl methacrylate.
4. The UV light curable pressure sensitive adhesive of claim 1, wherein: the monofunctional acrylate hard monomer is selected from any one or a combination of more of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobornyl methacrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate and tert-butyl acrylate.
5. The UV light curable pressure sensitive adhesive of claim 1, wherein: the multifunctional acrylate monomer containing at least two polymerizable double bonds per molecule is selected from any one or a combination of a plurality of ethylene glycol diacrylate, hexanediol diacrylate, tripropylene glycol diacrylate, butanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate, allyl acrylate, trimethylolpropane triacrylate and trimethylolpropane trimethacrylate.
6. The UV light curable pressure sensitive adhesive of claim 1, wherein: the UV photoinitiator is selected from any one or a combination of a plurality of 2-hydroxy-2-methyl-1-phenyl-1-acetone, diphenyl ketone, benzil dimethyl ether, benzoin dimethyl ether and benzoin isopropyl ether.
7. Use of a UV light curable pressure sensitive adhesive as claimed in claim 1, wherein: and coating the UV light-cured pressure-sensitive adhesive on a substrate film through a film coater, and then placing the substrate film under an ultraviolet irradiation device for light curing to prepare the pressure-sensitive adhesive product.
8. The use according to claim 7, characterized in that: the UV light curing pressure-sensitive adhesive is coated on a PET film through a 50 μm film coater, and then is placed on a conveyor belt type UV machine to carry out one-time illumination at a conveying speed of 0.1m/s and an illumination power of 2000W to prepare the pressure-sensitive adhesive product.
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