CN116694237A - UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, and preparation method and application thereof - Google Patents
UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, and preparation method and application thereof Download PDFInfo
- Publication number
- CN116694237A CN116694237A CN202310734974.1A CN202310734974A CN116694237A CN 116694237 A CN116694237 A CN 116694237A CN 202310734974 A CN202310734974 A CN 202310734974A CN 116694237 A CN116694237 A CN 116694237A
- Authority
- CN
- China
- Prior art keywords
- sensitive adhesive
- acrylate
- pressure
- light
- acrylic pressure
- 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.)
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 109
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 29
- 238000001723 curing Methods 0.000 claims abstract description 23
- -1 acrylic ester Chemical class 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 238000000576 coating method Methods 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 19
- 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 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 17
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 13
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 10
- 239000012790 adhesive layer Substances 0.000 claims description 10
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 10
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 9
- 244000028419 Styrax benzoin Species 0.000 claims description 9
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 9
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 9
- 229960002130 benzoin Drugs 0.000 claims description 9
- 235000019382 gum benzoic Nutrition 0.000 claims description 9
- 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 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 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 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 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 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 23
- 238000001035 drying Methods 0.000 abstract description 8
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 238000003848 UV Light-Curing Methods 0.000 abstract description 4
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 36
- 230000001070 adhesive effect Effects 0.000 description 24
- 239000000853 adhesive Substances 0.000 description 22
- 239000003292 glue Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 239000003522 acrylic cement Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- NWWQVENFTIRUMF-UHFFFAOYSA-N diphenylphosphanyl 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OP(C=1C=CC=CC=1)C1=CC=CC=C1 NWWQVENFTIRUMF-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 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
-
- 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
- C09J7/10—Adhesives in the form of films or foils without carriers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, a preparation method and application thereof, wherein the pressure-sensitive adhesive comprises the following raw material components in percentage by mass: monofunctional acrylate soft monomer: 60-80%; monofunctional acrylate hard monomer: 10-30%; polyfunctional monomers containing at least two polymerizable double bonds: 1 to 10 percent; acrylic ester functional monomer: 1 to 10 percent; and (3) a photoinitiator: 0.1 to 3 percent; the sum of the mass fractions of the components is 100. The pressure-sensitive adhesive provided by the invention can be prepared by directly and fully mixing the components according to the proportion at normal temperature, does not contain any solvent, has a simple preparation process, is environment-friendly and energy-saving, and is easy to realize scale; the pressure-sensitive adhesive product does not need heating, drying and curing, UV light curing solvent-free volatilization does not need recycling equipment, the curing mode is simple, energy consumption and heating are not needed through an oven, a large amount of cost can be saved, and the product competitiveness is improved.
Description
Technical Field
The invention relates to the field of pressure-sensitive adhesive materials, in particular to a UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, a preparation method and application thereof.
Background
Pressure Sensitive Adhesives (PSA) are a type of Pressure sensitive adhesive that are used primarily to make Pressure sensitive tapes. The adhesive can be firmly adhered to the surface of an adherend only by applying finger touch pressure.
Gradually enters the industrial field from the 20 th century, is widely used in various fields of packaging, building, vehicle-mounted, medical treatment, electronics, daily life and the like, and the pressure-sensitive adhesive product industry is rapidly developed in various countries of the world along with the progress of the age. The preparation process of the pressure-sensitive adhesive commonly used at present comprises the following steps: emulsion, solvent, hot melt, and the like. The solvent-based pressure-sensitive adhesive has good adhesive property, and can be directly adhered to the surface of polyolefin without treatment, but because the solvent-based pressure-sensitive adhesive contains a large amount of organic solvent, the solvent needs a large amount of energy consumption after coating, is not easy to recover after volatilizing, is easy to cause environmental pollution and human body damage, and meanwhile, the organic solvent has inflammable, explosive and high toxicity, so that the practical problems increasingly limit the development of the solvent-based pressure-sensitive adhesive. The solvent used for the emulsion pressure-sensitive adhesive is generally pure water, is nontoxic and pollution-free, but the product has the defects of poor water resistance, small adhesion to low-polarity surfaces and the like, and has high energy consumption and low drying speed during coating, and the application end of a client is limited to a certain extent. Because the adhesive tape is required to be dried to remove the solvent in production, the adhesive thickness is limited by the properties of the solvent type pressure-sensitive adhesive and the emulsion type pressure-sensitive adhesive, and the thickness of the dry adhesive is generally not more than 0.2mm, so that thicker pressure-sensitive adhesive tape products cannot be manufactured. The hot-melt pressure-sensitive adhesive does not contain an organic solvent, belongs to the current preparation process with relatively environmental protection and low pollution, and has the defect of low temperature resistance and obvious creep deformation in recent years, and cannot be used in occasions with relatively high temperature. With the increasing awareness of environmental protection and the implementation of strategies for human sustainable development, the development of low-pollution or pollution-free environmental-friendly PSAs has become a necessary trend.
The UV photo-curing pressure-sensitive adhesive is a polymerization product with pressure-sensitive performance, which is formed by converting a liquid state into a solid state in a very short time by initiating a chemical reaction of monomer polymerization and crosslinking by generating active free radicals or cations after a photoinitiator (or a photosensitizer) in a curing material absorbs ultraviolet light under the irradiation of the ultraviolet light. The method has the characteristics of high initiation speed, low energy consumption and cost, no solvent contact, excellent pressure-sensitive performance of the crosslinked product and the like. The pressure-sensitive adhesive product has high use value, accords with the energy-saving and environment-friendly concept of China, and has very wide application value and development prospect.
The following problems are common in the prior art:
1. the traditional process is difficult to prepare the pressure-sensitive adhesive tape with thicker adhesive layer, a large amount of solvents are contained in the solvent type adhesive or the emulsion type adhesive, a large amount of energy sources are required to be consumed in coating and drying, and meanwhile, the drying effect is also considered, so that the dry adhesive thickness of the prepared pressure-sensitive adhesive tape is generally below 0.2 mm;
2. the pressure-sensitive adhesive tapes prepared from solvent-type, emulsion-type and hot-melt adhesives have common laminating effects on low-surface-energy plates such as glass plates, ABS plates and PP plates, the peeling force is generally below 1200g/25mm, and the laminating requirements of certain high-viscosity application occasions cannot be met;
3. the environmental pollution caused by solvent volatilization and energy consumption and the injury to human bodies cannot be recovered in a short period, and the concept of sustainable development, energy conservation and environmental protection pursued at present is not met;
4. the traditional preparation process and the coating process have higher cost and are limited in the development of the current society with more and more vigorous competition.
Therefore, there is a need in the art for improvements that provide a more reliable solution.
Disclosure of Invention
The invention aims to solve the technical problem of providing a UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, a preparation method and application thereof aiming at the defects in the prior art.
In order to solve the technical problems, the invention adopts the following technical scheme: the invention provides a UV light-cured acrylic pressure-sensitive adhesive, which comprises the following raw material components in percentage by mass:
monofunctional acrylate soft monomer: 60-80%;
monofunctional acrylate hard monomer: 10-30%;
polyfunctional monomers containing at least two polymerizable double bonds: 1 to 10 percent;
acrylic ester functional monomer: 1 to 10 percent;
and (3) a photoinitiator: 0.1 to 3 percent;
the sum of the mass fractions of the components is 100.
Preferably, the monofunctional acrylate soft monomer is selected from the group consisting of: a mixture of one or more of n-butyl acrylate, isobutyl acrylate, isooctyl acrylate, lauryl acrylate, isooctyl methacrylate, lauryl methacrylate, 2-ethylhexyl acrylate.
Preferably, the monofunctional acrylate hard monomer is selected from the group consisting of: one or more of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, isobornyl acrylate and isobornyl methacrylate.
Preferably, the multifunctional monomer containing at least two polymerizable double bonds is selected from: ethylene glycol diacrylate, hexanediol diacrylate, ethoxylated bisphenol A dimethacrylate, butylene glycol diacrylate, allyl acrylate, trimethylolpropane triacrylate, 1, 6-hexanediol diacrylate.
Preferably, the acrylate functional monomer is selected from: one or more of acrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, acrylamide, and glycidyl acrylate.
Preferably, the photoinitiator is selected from: benzoin diethyl ether (Omnirad 651), 1-hydroxycyclohexyl phenyl ketone (Irgacure 184), diphenyl- (2, 4, 6-trimethylbenzoyl) oxy-phosphorus (TPO), diphenyl- (2, 4, 6-trimethylbenzoyl) oxy-phosphorus (Irgacure 819), 2-methyl-4-methylsulfanyl-2-morpholinophenone (Irgacure 907), 2-hydroxy-2 methyl-1-phenylpropion (Darocure 1173).
In a second aspect of the present invention, there is provided a method for preparing the UV photo-curable acrylic pressure-sensitive adhesive as described above, comprising the steps of:
s1, preparing prepolymer:
uniformly mixing a monofunctional acrylate soft monomer, a monofunctional acrylate hard monomer, a multifunctional monomer with at least two polymerizable double bonds in part, an acrylate functional monomer and a part of photoinitiator, and then irradiating with UV light intensity to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) mixing the prepolymer obtained in the step (S1), the rest of polyfunctional monomers at least containing two polymerizable double bonds and the rest of photoinitiators, and uniformly stirring to obtain the UV photo-curing acrylic pressure-sensitive adhesive.
Preferably, the preparation method of the UV light-cured acrylic pressure-sensitive adhesive comprises the following steps:
s1, preparing prepolymer:
240g of isooctyl acrylate, 240g of butyl acrylate, 30g of isooctyl methacrylate, 48g of isobornyl acrylate, 6g of ethoxylated bisphenol A dimethacrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 0.6g of photoinitiator benzoin diethyl ether and 0.6g of photoinitiator 1-hydroxycyclohexyl phenyl ketone are added into a 1000ml reaction kettle, uniformly mixed, and then irradiated by a 2MW ultraviolet lamp with the wavelength of 365nm to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) adding 0.1 weight percent of 1, 6-hexanediol diacrylate, 0.25 weight percent of photoinitiator benzoin diethyl ether and 0.25 weight percent of photoinitiator 1-hydroxycyclohexyl phenyl ketone into the prepolymer obtained in the step (S1), and uniformly stirring to obtain the UV photocuring acrylic pressure-sensitive adhesive.
In a third aspect of the present invention, there is provided an application of the UV light-curable acrylic pressure-sensitive adhesive as described above, for preparing a pressure-sensitive adhesive article, the preparation method comprising: coating UV light-cured acrylic pressure-sensitive adhesive on the bottom release film, adhering the surface release film on the surface of the adhesive layer, and curing by UV light to obtain the pressure-sensitive adhesive product.
Preferably, the method for preparing the pressure-sensitive adhesive product comprises the following steps: coating UV light-cured acrylic acid pressure-sensitive adhesive on a bottom PET release film, adhering a surface PET release film on the surface of the adhesive layer, irradiating and curing with 5-30MW ultraviolet light, and controlling the total energy absorbed by curing to 3000-5000mj/cm 2 The pressure-sensitive adhesive product is obtained.
The beneficial effects of the invention are as follows:
the UV photo-curing pressure-sensitive adhesive provided by the invention can be prepared by directly and fully mixing the components according to the proportion at normal temperature, does not contain any solvent, has a simple preparation process, is environment-friendly and energy-saving, and is easy to realize scale;
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 unexpectedly good adhesive property, good laminating effect on low-surface-energy materials and wider application range;
the UV photo-curing pressure-sensitive adhesive disclosed by the invention is free of solvent contact in the whole process, energy is saved by coating without passing through an oven, and the UV photo-curing pressure-sensitive adhesive accords with the energy-saving, environment-friendly and sustainable development concept in China;
the preparation of the pressure-sensitive adhesive product by the UV light-cured pressure-sensitive adhesive is simple and easy to implement, the UV light-cured pressure-sensitive adhesive is only required to be coated on a PET release film of a substrate through a film coater, meanwhile, the film coating operation is carried out on glue, and then the glue is placed under an ultraviolet irradiation device for light curing, so that the pressure-sensitive adhesive product can be prepared, the operation is simple, the film can be cured by only adjusting proper light intensity, thicker adhesive tapes can be prepared according to requirements, the environment is protected, the energy is saved, and the large-scale implementation is easy;
the pressure-sensitive adhesive product prepared by the UV light-cured pressure-sensitive adhesive does not need heating, drying and curing, does not volatilize solvent and does not need recycling equipment in the UV light-cured process, has a simple curing mode, does not need energy heating through an oven, can save a large amount of cost, and improves the competitiveness of the product.
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The test methods used in the following examples are conventional methods unless otherwise specified. The material reagents and the like used in the following examples are commercially available unless otherwise specified. The following examples were conducted under conventional conditions or conditions recommended by the manufacturer, without specifying the specific conditions. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The invention provides a UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive which comprises the following raw material components in parts by mass:
monofunctional acrylate soft monomer: 60-80%;
monofunctional acrylate hard monomer: 10-30%;
polyfunctional monomers containing at least two polymerizable double bonds: 1 to 10 percent;
acrylic ester functional monomer: 1 to 10 percent;
and (3) a photoinitiator: 0.1 to 3 percent;
the sum of the mass fractions of the components is 100.
In a preferred embodiment, the monofunctional acrylate soft monomer is selected from the group consisting of: a mixture of one or more of n-butyl acrylate, isobutyl acrylate, isooctyl acrylate, lauryl acrylate, isooctyl methacrylate, lauryl methacrylate, 2-ethylhexyl acrylate.
In a preferred embodiment, the monofunctional acrylate hard monomer is selected from the group consisting of: one or more of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, isobornyl acrylate and isobornyl methacrylate.
In a preferred embodiment, the multifunctional monomer containing at least two polymerizable double bonds is selected from: ethylene glycol diacrylate, hexanediol diacrylate, ethoxylated bisphenol A dimethacrylate, butylene glycol diacrylate, allyl acrylate, trimethylolpropane triacrylate, 1, 6-hexanediol diacrylate.
In a preferred embodiment, the acrylate functional monomer is selected from the group consisting of: one or more of acrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, acrylamide, and glycidyl acrylate.
In a preferred embodiment, the photoinitiator is selected from the group consisting of: benzoin diethyl ether (Omnirad 651), 1-hydroxycyclohexyl phenyl ketone (Irgacure 184), diphenyl- (2, 4, 6-trimethylbenzoyl) oxy-phosphorus (TPO), diphenyl- (2, 4, 6-trimethylbenzoyl) oxy-phosphorus (Irgacure 819), 2-methyl-4-methylsulfanyl-2-morpholinophenone (Irgacure 907), 2-hydroxy-2 methyl-1-phenylpropion (Darocure 1173). The photoinitiator belongs to a free radical initiator, and the substances absorb energy with a certain wavelength under ultraviolet light so as to generate free radicals to initiate double bond polymerization to form a stable adhesive layer.
The invention also provides a preparation method of the UV light-cured acrylic pressure-sensitive adhesive, which comprises the following steps:
s1, preparing prepolymer:
uniformly mixing a monofunctional acrylate soft monomer, a monofunctional acrylate hard monomer, a multifunctional monomer with at least two polymerizable double bonds in part, an acrylate functional monomer and a part of photoinitiator, and then irradiating with UV light intensity to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) mixing the prepolymer obtained in the step (S1), the rest of polyfunctional monomers at least containing two polymerizable double bonds and the rest of photoinitiators, and uniformly stirring to obtain the UV photo-curing acrylic pressure-sensitive adhesive.
The invention also provides an application of the UV light curing acrylic pressure-sensitive adhesive, and a method for preparing the pressure-sensitive adhesive product comprises the following steps: coating UV light-cured acrylic acid pressure-sensitive adhesive on a bottom PET release film by a film coater capable of freely adjusting thickness, adhering a surface PET release film on the surface of the adhesive layer to isolate oxygen from polymerization inhibition, curing by 5-30MW ultraviolet irradiation, and controlling the total curing absorption energy to 3000-5000mj/cm 2 The pressure-sensitive adhesive product is obtained.
The foregoing is a general inventive concept and the following detailed examples and comparative examples are provided on the basis thereof to further illustrate the invention.
Example 1
The preparation method of the UV light-cured acrylic pressure-sensitive adhesive comprises the following steps:
s1, preparing prepolymer:
240g of isooctyl acrylate, 240g of butyl acrylate, 30g of isooctyl methacrylate, 48g of isobornyl acrylate, 6g of ethoxylated bisphenol A dimethacrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 0.6g of photoinitiator benzoin diethyl ether (651) and 0.6g of photoinitiator 1-hydroxycyclohexyl phenyl ketone (184) are added into a 1000ml reaction kettle, uniformly mixed, and then irradiated by a 2MW ultraviolet lamp with the wavelength of 365nm to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) adding 0.1 weight percent of 1, 6-hexanediol diacrylate, 0.25 weight percent of photoinitiator benzoin diethyl ether and 0.25 weight percent of photoinitiator 1-hydroxycyclohexyl phenyl ketone into the prepolymer obtained in the step (S1), and uniformly stirring to obtain the UV photocuring acrylic pressure-sensitive adhesive.
The UV light-cured acrylic pressure-sensitive adhesive is prepared into a pressure-sensitive adhesive product by the following method:
coating UV light-cured acrylic pressure-sensitive adhesive on a bottom PET release film by a film coater with freely adjustable thickness, and adhering a surface PET release film on the surface of the adhesive layer to isolate oxygen from polymerization inhibition, wherein a 10MW UV mercury lamp is usedIrradiation curing, controlling the total energy absorbed by curing to 3500mj/cm 2 And (5) normally rolling and placing for 24 hours after the light curing is finished, so as to obtain the pressure-sensitive adhesive product. Wherein, through adjusting the coating gap of the film coater to be 100+ -5 um and 300+ -10 um respectively, pressure-sensitive adhesive products with two glue layer thicknesses can be obtained, which are respectively marked as examples 1-1 and 1-2, and are specifically shown in the following table 1.
Example 2
The preparation method of the UV light-cured acrylic pressure-sensitive adhesive comprises the following steps:
s1, preparing prepolymer:
360g of isooctyl acrylate, 120g of butyl acrylate, 30g of isooctyl methacrylate, 48g of isobornyl acrylate, 6g of 1, 6-hexanediol diacrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 907 photoinitiator 0.6g and 1173 photoinitiator 0.6g are added into a 1000ml reaction kettle, uniformly mixed, and then irradiated by a 2MW ultraviolet lamp with the wavelength of 365nm to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) adding 0.1 weight percent of 1, 6-hexanediol diacrylate, 0.25 weight percent of photoinitiator 907 and 0.25 weight percent of photoinitiator 1173 into the prepolymer obtained in the step (S1), and uniformly stirring to obtain the UV photocuring acrylic pressure-sensitive adhesive.
The UV light-cured acrylic pressure-sensitive adhesive is prepared into a pressure-sensitive adhesive product by the following method:
coating UV light-cured acrylic acid pressure-sensitive adhesive on a bottom PET release film by a film coater capable of freely adjusting thickness, adhering a surface PET release film on the surface of the adhesive layer to isolate oxygen from polymerization inhibition, irradiating and curing by a 10MW UV mercury lamp, and controlling the total energy of curing absorption to 3500mj/cm 2 And (5) normally rolling and placing for 24 hours after the light curing is finished, so as to obtain the pressure-sensitive adhesive product. Wherein, through adjusting the coating gap of the film coater to be 100+ -5 um and 300+ -10 um respectively, pressure-sensitive adhesive products with two glue layer thicknesses can be obtained, which are respectively recorded as example 2-1 and example 2-2, and are specifically shown in the following table 1.
Example 3
The preparation method of the UV light-cured acrylic pressure-sensitive adhesive comprises the following steps:
s1, preparing prepolymer:
480g of isooctyl acrylate, 30g of isooctyl methacrylate, 48g of isobornyl acrylate, 6g of trimethylolpropane triacrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 0.6g of 651 photoinitiator and 0.6g of 1173 photoinitiator are added into a 1000ml reaction kettle, uniformly mixed, and then irradiated by a 2MW ultraviolet lamp with the wavelength of 365nm to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) adding 0.1 weight percent of 1, 6-hexanediol diacrylate, 0.25 weight percent of photoinitiator 651 and 0.25 weight percent of photoinitiator 1173 into the prepolymer obtained in the step (S1), and uniformly stirring to obtain the UV photocuring acrylic pressure-sensitive adhesive.
The UV light-cured acrylic pressure-sensitive adhesive is prepared into a pressure-sensitive adhesive product by the following method:
coating UV light-cured acrylic acid pressure-sensitive adhesive on a bottom PET release film by a film coater capable of freely adjusting thickness, adhering a surface PET release film on the surface of the adhesive layer to isolate oxygen from polymerization inhibition, irradiating and curing by a 10MW UV mercury lamp, and controlling the total energy of curing absorption to 3500mj/cm 2 And (5) normally rolling and placing for 24 hours after the light curing is finished, so as to obtain the pressure-sensitive adhesive product. Wherein, through adjusting the coating gap of the film coater to be 100+ -5 um and 300+ -10 um respectively, pressure-sensitive adhesive products with two glue layer thicknesses can be obtained, which are respectively marked as example 3-1 and example 3-2, and are specifically shown in the following table 1.
Comparative example 1
The preparation method of the solvent type acrylic adhesive comprises the following steps:
1) 360g of isooctyl acrylate, 120g of butyl acrylate, 36g of isooctyl methacrylate, 48g of isobornyl acrylate, 18g of acrylic acid and 18g of hydroxyethyl acrylate are respectively weighed, 2.4g of benzoyl peroxide serving as an initiator is prepared, and 900g of mixed solvent (ethyl acetate and toluene are uniformly mixed according to a volume ratio of 2:1) is obtained for later use.
2) 300g of isooctyl acrylate, 100g of butyl acrylate, 30g of isooctyl methacrylate, 40g of isobornyl acrylate, 15g of acrylic acid, 15g of hydroxyethyl acrylate and 450g of mixed solvent are put into a reaction kettle and heated to 70-90 ℃.
3) 1.2g of initiator benzoyl peroxide is dissolved in 25g of mixed solvent to obtain initiator solution, all the initiator solution is added into a reaction kettle, and the reaction is carried out for 120min at 70-90 ℃ to obtain a prepolymer.
4) Uniformly mixing 60g of the rest isooctyl acrylate, 20g of butyl acrylate, 6g of isooctyl methacrylate, 8g of isobornyl acrylate, 3g of acrylic acid, 3g of hydroxyethyl acrylate, 0.4g of benzoyl peroxide serving as an initiator and 225g of solvent, dropwise adding the mixture into a prepolymer for 90min, keeping the temperature at 70-90 ℃, and keeping the temperature for 90min after the completion of dropwise adding to obtain an intermediate product A.
5) Adding the rest initiator 0.8g into the intermediate product A, and preserving the temperature for 120min at 70-90 ℃ to obtain an intermediate product B.
6) 200g of the rest mixed solvent is added into the intermediate product B, the temperature is kept at 70-90 ℃ for 90min, and the temperature is reduced to below 40 ℃ to obtain the acrylic ester adhesive synthesized by the solvent method.
7) Taking out a proper amount of the acrylate adhesive obtained in the step 6) after polymerization, adding 0.1 weight percent of 1, 6-hexanediol diacrylate and 0.50 weight percent of initiator benzoyl peroxide according to the proportion, and stirring uniformly to obtain the glue with the viscosity required by coating.
The glue obtained in the step 7) is prepared into a glue film product by adopting the following method:
glue is directly coated on a substrate PET release film, and the solvent is dried by an oven to be cured into the pressure-sensitive adhesive film with good performance. The coating gap was 100.+ -.5 um and the 8-section oven temperature was set at 50deg.C/70 ℃/90 ℃/100 ℃/120 ℃/120 ℃/90 ℃/70 ℃. And (5) normally winding and placing for 24 hours after the high-temperature drying is finished, so that the required acrylate adhesive film product can be obtained.
Comparative example 2
An emulsion type acrylic adhesive, the preparation method comprises the following steps:
1) 360g of isooctyl acrylate, 120g of butyl acrylate, 36g of isooctyl methacrylate, 48g of isobornyl acrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 2.4g of initiator ammonium persulfate, 6g of anionic surfactant sodium dodecyl diphenyl ether disulfonate, 2g of nonionic surfactant octyl phenol polyoxyethylene ether and 450g of deionized water are respectively weighed for standby.
2) 300g of deionized water, 1.2g of initiator ammonium persulfate, 4.5g of anionic surfactant sodium dodecyl diphenyl ether disulfonate and 1.5g of nonionic surfactant octyl phenol polyoxyethylene ether are simultaneously put into a pre-emulsifying kettle to be stirred and dispersed for 30min at high speed.
3) After the stirring is finished, 360g of all isooctyl acrylate, 120g of butyl acrylate, 36g of isooctyl methacrylate, 48g of isobornyl acrylate, 18g of acrylic acid and 18g of hydroxyethyl acrylate are added into a pre-emulsifying kettle, the high-speed stirring can not be closed or reduced while the feeding is finished, the high-speed stirring and dispersing are continued for 30min for pre-emulsifying operation, and the emulsification is finished and standing is not layered for standby.
4) Adding the rest anionic surfactant sodium dodecyl diphenyl ether disulfonate 1.5g, nonionic surfactant octyl phenol polyoxyethylene ether 0.5g and deionized water 100g into a reaction kettle simultaneously to serve as a base solution, starting low-speed stirring, and heating to 80-90 ℃.
5) The remaining initiator ammonium persulfate 1.2g was dissolved with the remaining 50g deionized water. Meanwhile, the pre-emulsion and the initiator are added into the reaction kettle in a dropwise manner for 180min, the dropwise addition time of the initiator is 210min, the temperature in the reaction kettle is kept at 85-90 ℃ in the dropwise addition process, and the temperature is kept for 60min after the dropwise addition is completed.
6) After the heat preservation is completed, the system is cooled to 65-75 ℃, 0.5g of suspended white block and 0.5g of tertiary butyl hydroperoxide are respectively added for carrying out the elimination reaction, and the heat preservation is carried out for 30min.
7) And (3) cooling the system to below 40 ℃ after heat preservation is finished, adding 14% ammonia water to adjust the pH to 7-8, discharging and filtering to obtain the acrylic ester adhesive synthesized by the emulsion method.
8) Taking out a proper amount of the polymerized acrylic adhesive obtained in the step 7), adding 0.1 weight percent of aziridine crosslinking agent SAC-100 according to a proportion, and uniformly stirring to obtain the glue with the viscosity required by coating.
The glue obtained in the step 8) is prepared into a glue film product by adopting the following method:
glue is directly coated on a substrate PET release film, and moisture is dried by an oven, so that the pressure-sensitive adhesive film with good performance is formed by curing. The coating gap was 100.+ -.5 um and the 8-section oven temperature was set at 50deg.C/70 ℃/90 ℃/100 ℃/120 ℃/120 ℃/90 ℃/70 ℃. And (5) normally winding and placing for 24 hours after the high-temperature drying is finished, so that the required acrylate adhesive film product can be obtained.
The pressure-sensitive adhesive articles/acrylic adhesive film articles prepared in examples 1-3 and comparative examples 1-2 were subjected to the following performance tests, and the test items and methods were as follows:
1. peel strength: 180 DEG peel strength was tested according to GB/T2792 method;
2. temperature-resistant shear test: testing according to GB/T4851 method;
3. tensile length and elongation at break test: testing according to the GB/T1040 method;
4. annular primary tack test: testing according to the GB/T22396 method;
5. and (3) adhesive film thickness test: tested according to ASTM D3652 method.
The test results are shown in table 1 below:
TABLE 1
As can be seen from the test results in table 1, the thickness of the product is limited due to the curing and drying requirements of the solvent-type or emulsion-type adhesive, and the UV-curable adhesive can meet more thickness requirements; in the aspect of bonding different materials, the UV curing adhesive has great advantages in preparing products, and the 180-degree stripping force of the adhesive on different surface energy materials such as steel plates, glass plates, ABS plates, PC plates and the like is more than 2-5 times that of solvent type or emulsion type products, so that the adhesive has better bonding performance and wider bonding application occasions; the product prepared from the UV curing adhesive is far superior to the traditional adhesives such as solvent type or emulsion type in high-temperature shearing resistance; the UV type adhesive is also superior to the traditional adhesive products such as solvent type or emulsion type in the aspects of tensile strength and elongation at break, which shows that the UV type adhesive products have higher strength and toughness and wider application occasions; from the comprehensive table-the test results, the pressure-sensitive adhesive products prepared from the UV-type adhesives prepared in examples 1 to 3 have more excellent comprehensive properties, and the overall properties are significantly better than those of the solvent-type acrylic adhesives (comparative example 1) and the emulsion-type acrylic adhesives (comparative example 2) prepared by the conventional scheme.
Although embodiments of the present invention have been disclosed above, it is not limited to the use of the description and embodiments, it is well suited to various fields of use for the invention, and further modifications may be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the particular details without departing from the general concepts defined in the claims and the equivalents thereof.
Claims (10)
1. The UV photo-curing acrylic pressure-sensitive adhesive is characterized by comprising the following raw material components in percentage by mass:
monofunctional acrylate soft monomer: 60-80%;
monofunctional acrylate hard monomer: 10-30%;
polyfunctional monomers containing at least two polymerizable double bonds: 1 to 10 percent;
acrylic ester functional monomer: 1 to 10 percent;
and (3) a photoinitiator: 0.1 to 3 percent;
the sum of the mass fractions of the components is 100.
2. The UV light curable acrylic pressure sensitive adhesive according to claim 1, wherein the monofunctional acrylate-based soft monomer is selected from the group consisting of: a mixture of one or more of n-butyl acrylate, isobutyl acrylate, isooctyl acrylate, lauryl acrylate, isooctyl methacrylate, lauryl methacrylate, 2-ethylhexyl acrylate.
3. The UV light curable acrylic pressure sensitive adhesive according to claim 1, wherein the mono-functional acrylate hard monomer is selected from the group consisting of: one or more of methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, isobornyl acrylate and isobornyl methacrylate.
4. The UV curable acrylic pressure sensitive adhesive according to claim 1, wherein the multifunctional monomer containing at least two polymerizable double bonds is selected from the group consisting of: ethylene glycol diacrylate, hexanediol diacrylate, ethoxylated bisphenol A dimethacrylate, butylene glycol diacrylate, allyl acrylate, trimethylolpropane triacrylate, 1, 6-hexanediol diacrylate.
5. The UV light-curable acrylic pressure sensitive adhesive according to claim 1, wherein the acrylate functional monomer is selected from the group consisting of: one or more of acrylic acid, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, acrylamide, and glycidyl acrylate.
6. The UV light-curable acrylic pressure sensitive adhesive according to claim 1, wherein the photoinitiator is selected from the group consisting of: benzoin diethyl ether, 1-hydroxycyclohexyl phenyl ketone, diphenyl- (2, 4, 6-trimethylbenzoyl) phosphorus oxide, 2-methyl-4-methylthio-2-morpholinophenone, 2-hydroxy-2-methyl-1-phenylpropion.
7. A method for preparing the UV light-curable acrylic pressure-sensitive adhesive according to any one of claims 1 to 6, comprising the steps of:
s1, preparing prepolymer:
uniformly mixing a monofunctional acrylate soft monomer, a monofunctional acrylate hard monomer, a multifunctional monomer with at least two polymerizable double bonds in part, an acrylate functional monomer and a part of photoinitiator, and then irradiating with UV light intensity to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) mixing the prepolymer obtained in the step (S1), the rest of polyfunctional monomers at least containing two polymerizable double bonds and the rest of photoinitiators, and uniformly stirring to obtain the UV photo-curing acrylic pressure-sensitive adhesive.
8. The method for preparing a UV light-curable acrylic pressure-sensitive adhesive according to claim 7, comprising the steps of:
s1, preparing prepolymer:
240g of isooctyl acrylate, 240g of butyl acrylate, 30g of isooctyl methacrylate, 48g of isobornyl acrylate, 6g of ethoxylated bisphenol A dimethacrylate, 18g of acrylic acid, 18g of hydroxyethyl acrylate, 0.6g of photoinitiator benzoin diethyl ether and 0.6g of photoinitiator 1-hydroxycyclohexyl phenyl ketone are added into a 1000ml reaction kettle, uniformly mixed, and then irradiated by a 2MW ultraviolet lamp with the wavelength of 365nm to obtain a prepolymer;
s2, preparing a pressure-sensitive adhesive:
and (2) adding 0.1 weight percent of 1, 6-hexanediol diacrylate, 0.25 weight percent of photoinitiator benzoin diethyl ether and 0.25 weight percent of photoinitiator 1-hydroxycyclohexyl phenyl ketone into the prepolymer obtained in the step (S1), and uniformly stirring to obtain the UV photocuring acrylic pressure-sensitive adhesive.
9. Use of a UV light-curable acrylic pressure-sensitive adhesive according to any one of claims 1 to 6 for the preparation of pressure-sensitive adhesive articles, comprising: coating UV light-cured acrylic pressure-sensitive adhesive on the bottom release film, adhering the surface release film on the surface of the adhesive layer, and curing by UV light to obtain the pressure-sensitive adhesive product.
10. The use of a UV light-curable acrylic pressure-sensitive adhesive according to claim 9, characterized in that it is used for the preparation of pressure-sensitive adhesive articles by the process of: coating UV light-cured acrylic pressure-sensitive adhesive on the bottom PET layer
On the release film, the surface of the adhesive layer is coated with a surface PET release film, and is cured by 5-30MW ultraviolet irradiation,
controlling the total energy of solidification and absorption to be 3000-5000mj/cm 2 The pressure-sensitive adhesive product is obtained.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310734974.1A CN116694237A (en) | 2023-06-20 | 2023-06-20 | UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310734974.1A CN116694237A (en) | 2023-06-20 | 2023-06-20 | UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, and preparation method and application thereof |
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| CN116694237A true CN116694237A (en) | 2023-09-05 |
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| CN202310734974.1A Pending CN116694237A (en) | 2023-06-20 | 2023-06-20 | UV (ultraviolet) photo-curing acrylic pressure-sensitive adhesive, and preparation method and application thereof |
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| Country | Link |
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| CN (1) | CN116694237A (en) |
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2023
- 2023-06-20 CN CN202310734974.1A patent/CN116694237A/en active Pending
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