CN112226164A - Photocuring magnetic-conduction light pressure-sensitive adhesive, adhesive tape and preparation method thereof - Google Patents
Photocuring magnetic-conduction light pressure-sensitive adhesive, adhesive tape and preparation method thereof Download PDFInfo
- Publication number
- CN112226164A CN112226164A CN202010906511.5A CN202010906511A CN112226164A CN 112226164 A CN112226164 A CN 112226164A CN 202010906511 A CN202010906511 A CN 202010906511A CN 112226164 A CN112226164 A CN 112226164A
- Authority
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- China
- Prior art keywords
- parts
- magnetic
- resin
- sensitive adhesive
- photocuring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 53
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000002390 adhesive tape Substances 0.000 title abstract description 8
- 239000011347 resin Substances 0.000 claims abstract description 58
- 229920005989 resin Polymers 0.000 claims abstract description 58
- 230000001070 adhesive effect Effects 0.000 claims abstract description 25
- 239000000853 adhesive Substances 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 239000000945 filler Substances 0.000 claims abstract description 20
- 239000004593 Epoxy Substances 0.000 claims abstract description 18
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 16
- 239000011231 conductive filler Substances 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 239000003085 diluting agent Substances 0.000 claims abstract description 15
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 14
- 239000007822 coupling agent Substances 0.000 claims abstract description 13
- 239000002270 dispersing agent Substances 0.000 claims abstract description 13
- 239000006254 rheological additive Substances 0.000 claims abstract description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 12
- -1 sodium carboxyethyl benzoate Chemical compound 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000011159 matrix material Substances 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- JOIXGDNGAXHWPO-UHFFFAOYSA-N 3,5-dihydroxycyclohexane-1-carboxylic acid Chemical compound OC1CC(O)CC(C(O)=O)C1 JOIXGDNGAXHWPO-UHFFFAOYSA-N 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 8
- 229920000647 polyepoxide Polymers 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 229920000120 polyethyl acrylate Polymers 0.000 claims description 7
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- DKSRMPBSDVNYQU-UHFFFAOYSA-N [Na].C(C=C)(=O)OCCCO Chemical compound [Na].C(C=C)(=O)OCCCO DKSRMPBSDVNYQU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000956 alloy Substances 0.000 claims description 5
- 229910045601 alloy Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000003505 terpenes Chemical class 0.000 claims description 5
- 235000007586 terpenes Nutrition 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 4
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 3
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- RBQLGIKHSXQZTB-UHFFFAOYSA-N 3-methylpentane-2,4-diol Chemical compound CC(O)C(C)C(C)O RBQLGIKHSXQZTB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 229920002253 Tannate Polymers 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004337 hydroquinone Drugs 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 3
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 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 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940070765 laurate Drugs 0.000 claims description 2
- BBEMTSQNNCZDQJ-UHFFFAOYSA-N n-(2-aminoethyl)-n-ethylprop-2-enamide Chemical compound NCCN(CC)C(=O)C=C BBEMTSQNNCZDQJ-UHFFFAOYSA-N 0.000 claims description 2
- PTSPHFGZMBDNJN-UHFFFAOYSA-N n-ethyl-n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCN(CC)C(=O)C=C PTSPHFGZMBDNJN-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 description 11
- 238000001723 curing Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 238000000889 atomisation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 2
- 239000004808 2-ethylhexylester Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010019909 Hernia Diseases 0.000 description 2
- 206010051246 Photodermatosis Diseases 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- TZEKUJKAULMISU-UHFFFAOYSA-N n-(2,2-dihydroxyethyl)prop-2-enamide Chemical compound OC(O)CNC(=O)C=C TZEKUJKAULMISU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000008845 photoaging Effects 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UZONFOPDCXAZND-UHFFFAOYSA-N 1-nitroheptane Chemical compound CCCCCCC[N+]([O-])=O UZONFOPDCXAZND-UHFFFAOYSA-N 0.000 description 1
- MHDULSOPQSUKBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical group ClC1=CC=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MHDULSOPQSUKBQ-UHFFFAOYSA-N 0.000 description 1
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- IHLRGGLJGGTPCY-UHFFFAOYSA-N hept-5-en-3-one Chemical compound CCC(=O)CC=CC IHLRGGLJGGTPCY-UHFFFAOYSA-N 0.000 description 1
- OVMJVEMNBCGDGM-UHFFFAOYSA-N iron silver Chemical compound [Fe].[Ag] OVMJVEMNBCGDGM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Classifications
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- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0856—Iron
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2296—Oxides; Hydroxides of metals of zinc
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/01—Magnetic additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
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Abstract
A photocuring magnetic-conductive photosensitive pressure-sensitive adhesive, an adhesive tape and a preparation method thereof comprise the following components in parts by weight: 30-40 parts of modified functional resin, 60-80 parts of aliphatic epoxy modified acrylate resin, 5-15 parts of functional monomer, 10-30 parts of diluent, 0.5-1 part of photoinitiator, 5-10 parts of light guide filler, 8-12 parts of magnetic conductive filler, 1-3 parts of rheological additive, 0.5-1.8 parts of flatting agent, 1-2.5 parts of dispersing agent, 0.8-2.4 parts of coupling agent, 1-3 parts of defoaming agent, 0.2-1 part of chain transfer agent and 20-50 parts of tackifying resin. The light-guiding and magnetic-conducting adhesive disclosed by the invention has excellent light guiding property and magnetic conductivity, is lightly crosslinked, is easy to adhere, can be easily peeled off, has certain temperature resistance, and can be widely applied to adhesion of various products needing light guiding and magnetic conducting.
Description
Technical Field
The invention relates to the technical field of adhesives, in particular to a photocuring magnetic-guide photosensitive pressure-sensitive adhesive, a photocuring magnetic-guide photosensitive pressure-sensitive adhesive tape and a preparation method thereof.
Background
The light-transmitting adhesive is used for special adhesives for gluing transparent optical elements (touch screens, displays, optical lenses and the like). The existing light-transmitting adhesive has the defects of easy yellowing, incapability of shielding electromagnetic interference and the like due to excessive pursuit of light transmittance.
With the wide application of electronic devices, the problems of electromagnetic wave interference and information leakage are receiving more and more attention, and many processes such as device assembly, testing and the like and some working environments need to be electromagnetically shielded to effectively reduce the radiation of electromagnetic waves, so that the electromagnetic shielding material is widely researched and applied. The magnetic conductive adhesive is widely applied to the fields of instruments and meters and the like because of good magnetic conductivity, the magnetic conductive adhesive is generally coated on the surface of a material to be shielded to form a shielding coating, most of the magnetic conductive adhesives are thermosetting materials, and are adhered to the surface of the material after being cured and crosslinked without being peeled off again, but when some components need to be frequently repaired and replaced, the magnetic conductive adhesives are difficult to clean and can damage the surface of the material or residual adhesive on the surface of the material during cleaning, so that the continuous use of the components is influenced, and in some occasions (such as component testing and the like), the components and instruments need to be temporarily shielded by the magnetic conductive adhesive, and the magnetic conductive adhesive is removed after the work is finished, so that the thermosetting magnetic conductive adhesive is not suitable for use in the occasions, and the magnetic conductive pressure sensitive adhesive can solve the problems, the magnetic conductive pressure sensitive adhesive is made into an adhesive tape and is, when not needed, the adhesive tape is peeled off.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a photocuring magnetic conduction light-guide pressure-sensitive adhesive which has excellent light-guide and magnetic-conduction performance and is convenient to strip and free of adhesive residue, a preparation method of the pressure-sensitive adhesive and a preparation method of a photocuring magnetic conduction light-guide pressure-sensitive adhesive tape prepared from the pressure-sensitive adhesive.
The invention is realized by the following technical scheme:
a photocuring magnetic guide photosensitive pressure-sensitive adhesive comprises the following components in parts by weight: 30-40 parts of modified functional resin, 60-80 parts of aliphatic epoxy modified acrylate resin, 5-15 parts of functional monomer, 10-30 parts of diluent, 0.5-1 part of photoinitiator, 5-10 parts of light guide filler, 8-12 parts of magnetic conductive filler, 1-3 parts of rheological additive, 0.5-1.8 parts of flatting agent, 1-2.5 parts of dispersing agent, 0.8-2.4 parts of coupling agent, 1-3 parts of defoaming agent and 0.2-1 part of chain transfer agent.
In order to make up for the requirement of initial viscosity of some use occasions, the components further comprise 20-50 parts of tackifying resin, wherein the tackifying resin is terpene resin or petroleum resin, has good compatibility with other components in a system, and has good auxiliary curing effect in a subsequent reaction process.
Further, the diluent is ethanol or/and 1, 6-hexanediol diacrylate (HDDA). The components in the dissolving system can be diluted by adding ethanol, so that the reaction can be continued, and the adhesive can be coated and used. The HDDA is an active diluent, has bifunctional active groups, has low viscosity, can reduce the viscosity of a system in the early reaction stage to ensure that the reaction is smoothly carried out, but can increase the curing degree of the system in the later reaction stage, increase the cohesive force and reduce the initial viscosity of the pressure-sensitive adhesive, so the using amount of the HDDA needs to be controlled.
Further, the aliphatic epoxy modified acrylate resin is colorless transparent liquid, the molecular weight is 5000-20000, and the viscosity at 25 ℃ is 5000-20000 mPas. The aliphatic epoxy modified acrylate resin can be prepared from alkyl epoxy resin, acrylic acid, butyl acrylate, isooctyl acrylate and the like, and the specific preparation process comprises the steps of reacting the acrylic acid with the alkyl epoxy resin, grafting reactive double bonds on the alkyl epoxy resin, and carrying out polymerization reaction on the grafted product, butyl acrylate and isooctyl acrylate. The molecular weight and viscosity of the product can be adjusted by the ratio of the monomer components to achieve the desired viscosity range. The acrylate resin is modified by epoxy, so that the cohesive strength of the product can be improved, and the heat resistance, chemical resistance and water resistance of the final pressure-sensitive adhesive product are improved.
Further preferably, the functional monomer is a polar monomer containing N atoms, and the polar monomer containing N atoms may be one or two of N-methylacrylamide, N-ethylacrylamide, N-methylolacrylamide, N-hydroxyethylacrylamide, diacetone acrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-ethyl-N-aminoethylacrylamide, N-ethyl-N-hydroxyethylacrylamide, N-dimethylolacrylamide, N-dihydroxyethylacrylamide, N-vinylpyrrolidone, and N-vinylcaprolactam.
In a further preferred embodiment, the chain transfer agent may be a commonly used chain transfer agent, such as alkyl mercaptan.
Further preferably, the photoinitiator is a polysubstituted polycyclic aromatic hydrocarbon photoinitiator selected from one of polysubstituted benzoin ethers and polysubstituted aromatic ketones, and the substituent is selected from phenyl, aryl or heteroaryl, C5-C6 cycloalkyl, C1-C12 alkyl substituted by-SH, -N (C1-C6 alkyl) 2, piperidino, morpholino, piperazino, -OH, -O (C1-C12 alkyl), -COOH, or C1-C12 alkoxy. The polysubstitution polycyclic aromatic hydrocarbon photoinitiator has a macromolecular structure, eliminates the mobility of the photoinitiator in the use process, improves the yellowing phenomenon, and particularly, the aromatic ring of the compound is coupled with a tertiary amine structure, so that the ultraviolet absorption wavelength red is shifted to 380-395nm, and unsaturated monomers can be effectively initiated to polymerize under the radiation of a UV lamp; in addition, the solvent property in the resin and oligomer is good.
The photoinitiator is preferably one of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetraphenylimidazole, 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine and 4-benzoyl-4' -methyl diphenyl sulfide. The photo-initiation auxiliary agent can greatly reduce the curing shrinkage rate of the pressure-sensitive adhesive while improving the photo-initiation efficiency, and the photo-curing efficiency of the pressure-sensitive adhesive is higher by matching with the action of the light guide filler.
The light guide filler is one of nano zinc oxide, nano titanium dioxide, polymethyl methacrylate micro powder and nano aluminum oxide with the particle size of 20-30 nm. The light guide filler has an extinction effect, has a smooth hand feeling, cannot absorb UV (ultraviolet), does not influence the absorption energy of a photoinitiator, simultaneously keeps transparent texture, has good heat resistance and dispersibility, and provides an excellent optical diffusion effect and a good high-refractive-index transparent brightness performance.
The magnetic conductive filler is one of nano iron powder, nickel powder, carbonyl iron powder, iron oxide and iron-based alloy powder with the particle size of 20-30 nm. The iron-based alloy powder can be a composite powder of iron and particles of nickel, silver and the like, and can also be a composite powder of iron oxide and particles of nickel, silver and the like. Magnetically conductive fillers are available by atomization techniques that achieve atomization of a molten metal stream into a liquid or gaseous medium, the essence of atomization being to melt a substantial volume of the precursor and to eject a substantial portion of the molten metal droplets into a gaseous or liquid environment.
The further preferable technical scheme is that the modified functional resin contains 100-118 terminal hydroxyl groups, and can be synthesized by the following steps:
s1, adding 1 part of 3-methylpentane-2, 4-diol and 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid into a closed container according to a molar ratio under the protection of inert gas and stirring, then adding concentrated sulfuric acid as a catalyst, stirring at 160-180 ℃ for 1-2 hours to perform condensation reaction, and obtaining a matrix A1 of the modified functional resin;
s2, adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A1 obtained in the step S1, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A2 of modified functional resin; adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A2, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A3 of modified functional resin; repeating the step 4 times until a matrix A7 of the modified functional resin is obtained;
s3, washing the matrix A7 of the modified functional resin obtained in the step S2, transferring the washed matrix A into a container, adding acrylic acid and 1, 4-benzenediol, stirring and reacting for 4 hours at 80 ℃, and washing the product to obtain the modified functional resin.
The modified functional resin has abundant terminal hydroxyl groups, is easy to react with other groups, and improves the crosslinking density of a product, so that the cohesive strength and the heat resistance are improved, and therefore, the adhesive is endowed with excellent anti-migration property, and components in the pressure-sensitive adhesive cannot migrate to the surface of an adhered material. The pressure-sensitive adhesive is added with the modified functional resin, so that the possibility of photochemical reaction can be eliminated or slowed down, and the photoaging process can be prevented or delayed; the modified functional resin has good compatibility with the main resin and good storage stability, and does not influence the interface performance of the pressure-sensitive adhesive.
The rheological additive can adjust the flow characteristic of the pressure-sensitive adhesive resin, the molecular weight is 7500-15000, as the concentration is increased, the molecules of the rheological additive are associated with each other to form a ring-shaped micelle, the hydrophobic component in the molecule faces to the inside of the micelle, and the hydrophilic middle chain segment forms an outer ring-shaped shell, so that the rheological characteristic of the pressure-sensitive adhesive can be changed by changing the concentration of the rheological additive.
Further preferably, the leveling agent is one or more selected from the group consisting of polyethylacrylate, polybutylacrylate, poly-2-ethylhexyl acrylate and polyethylacrylate. The leveling agent is beneficial to the dispersion of the filler, is beneficial to improving the light guide property and the magnetic conductivity, and plays a synergistic role.
The further preferable technical scheme is that the dispersing agent is one or more of sodium hydroxypropyl acrylate, sodium carboxyethyl benzoate and sodium dimethyl cellulose tannate.
The further preferable technical scheme is that the defoaming agent is one or more of epoxy pentane alcohol benzoate, nitro heptane alcohol laurate, dimethyl butyl alcohol isopropyldioleate and isobutyl octadecanol diethyltitanate.
The further preferable technical scheme is that the coupling agent is one or more of isobutyl vinyl dimethyl siloxane, propenyl butanone-based dichloro siloxane, isobutyl mercaptopropyl dimethyl ketoximino siloxane and dimethyl dichlorosilane.
A method for preparing the photocuring magnetic guide photosensitive pressure-sensitive adhesive comprises the following steps:
s1, firstly adding a certain amount of aliphatic epoxy modified acrylate resin and functional monomers into a reaction device provided with a stirring device, a reflux condensing device, a dripping device, a thermometer and a nitrogen introducing device, heating to 80 ℃, then adding a photoinitiator, a chain transfer agent and a defoaming agent which account for 5-10% of the total amount of the formula, carrying out polymerization reaction for 0.5h, then slowly dripping a leveling agent, a dispersing agent and the rest of the photoinitiator, the chain transfer agent and the defoaming agent, finishing dripping within 2h, maintaining the reflux state all the time in the dripping process, gradually increasing the temperature, after finishing dripping, adding a certain amount of modified functional resin, carrying out reflux reaction for 0.5h, stopping the reaction, and cooling to obtain a prepolymer;
s2, mixing absolute ethyl alcohol, rheological additive and coupling agent according to a specified proportion, taking the mixture as a diluent to dilute the prepolymer to a proper viscosity, adding magnetic conductive filler and light guide filler, and uniformly mixing to obtain the photocuring magnetic conductive photosensitive pressure-sensitive adhesive.
A preparation method of a photocuring magnetic-conductive light-conductive pressure-sensitive adhesive tape comprises the steps of coating the photocuring magnetic-conductive light-sensitive adhesive on a release film, drying at 120 ℃ for 10min, and then placing the film under an ultraviolet lamp for radiation crosslinking at a distance of 15cm to obtain the photocuring magnetic-conductive light-conductive pressure-sensitive adhesive tape. The UV light source is preferably a light source generated by a carbon arc lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a fluorescent lamp, a hernia lamp and the like, and the light source intensity, the emission stability and the light splitting energy distribution uniformity are good.
The light-conducting and magnetic-conducting adhesive is different from the conventional thermosetting light-conducting and magnetic-conducting adhesive, is lightly crosslinked, can be easily peeled off after being adhered to the surface of a material, has certain peeling strength and mechanical property due to the rigid structures such as crosslinking of a high molecular chain and the like, meets the use requirement, and can be used on a heating electronic element due to the certain temperature resistance of the special molecular structure; meanwhile, due to the flexible chain segments on the molecular chains, tackifying resin and other components, the adhesive has certain initial viscosity and can be easily adhered to the surface of a material; the light guide filler and the magnetic conductive filler in the adhesive component have excellent light guide property and magnetic conductivity, are not easy to yellow, and are widely applied to bonding of various products needing light guide and magnetic conduction; the ultraviolet curing mode is energy-saving and environment-friendly, the shrinkage rate in the processing and curing process is low, and the processing is convenient.
Detailed Description
A photocuring magnetic guide photosensitive pressure-sensitive adhesive comprises the following components in parts by weight: 30-40 parts of modified functional resin, 60-80 parts of aliphatic epoxy modified acrylate resin, 5-15 parts of functional monomer, 10-30 parts of diluent, 0.5-1 part of photoinitiator, 5-10 parts of light guide filler, 8-12 parts of magnetic conductive filler, 1-3 parts of rheological additive, 0.5-1.8 parts of flatting agent, 1-2.5 parts of dispersing agent, 0.8-2.4 parts of coupling agent, 1-3 parts of defoaming agent and 0.2-1 part of chain transfer agent.
In order to meet the requirement of initial viscosity of some use occasions, the components can also comprise 20-50 parts of tackifying resin, wherein the tackifying resin is terpene resin or petroleum resin, has good compatibility with other components in a system, and has good auxiliary curing effect in the subsequent reaction process.
The diluent is ethanol or/and 1, 6-hexanediol diacrylate (HDDA). The components in the dissolving system can be diluted by adding ethanol, so that the reaction can be continued, and the adhesive can be coated and used. The HDDA is an active diluent, has bifunctional active groups, has low viscosity, can reduce the viscosity of a system in the early reaction stage to ensure that the reaction is smoothly carried out, but can increase the curing degree of the system in the later reaction stage, increase the cohesive force and reduce the initial viscosity of the pressure-sensitive adhesive, so the using amount of the HDDA needs to be controlled.
The aliphatic epoxy modified acrylate resin is colorless transparent liquid, the molecular weight is 5000-20000, and the viscosity at 25 ℃ is 5000-20000 mPa. The aliphatic epoxy modified acrylate resin can be prepared from alkyl epoxy resin, acrylic acid, butyl acrylate, isooctyl acrylate and the like, and the specific preparation process comprises the steps of reacting the acrylic acid with the alkyl epoxy resin, grafting reactive double bonds on the alkyl epoxy resin, and carrying out polymerization reaction on the grafted product, butyl acrylate and isooctyl acrylate. The acrylate resin is modified by epoxy, so that the cohesive strength of the product can be improved, and the heat resistance, chemical resistance and water resistance of the final pressure-sensitive adhesive product are improved.
The functional monomer is a polar monomer containing N atoms, and the polar monomer containing N atoms can be one or two of N-methyl acrylamide, N-ethyl acrylamide, N-hydroxymethyl acrylamide, N-hydroxyethyl acrylamide, diacetone acrylamide, N-dimethyl acrylamide, N-diethyl acrylamide, N-ethyl-N-aminoethyl acrylamide, N-ethyl-N-hydroxyethyl acrylamide, N-dimethylol acrylamide, N-dihydroxyethyl acrylamide, N-vinyl pyrrolidone and N-vinyl caprolactam.
The photoinitiator is a polysubstituted polycyclic aromatic hydrocarbon photoinitiator, is selected from one of polysubstituted benzoin ether and polysubstituted aromatic ketone, and the substituent is selected from phenyl, aryl or heteroaryl, C5-C6 naphthenic base, C1-C12 alkyl substituted by-SH, -N (C1-C6 alkyl) 2, piperidino, morpholino, piperazino, -OH, -O (C1-C12 alkyl), -COOH, or C1-C12 alkoxy. The polysubstitution polycyclic aromatic hydrocarbon photoinitiator has a macromolecular structure, eliminates the mobility of the photoinitiator in the practical process, improves the yellowing phenomenon, and particularly, the aromatic ring of the compound is coupled with a tertiary amine structure, so that the ultraviolet absorption wavelength red is shifted to 380-395nm, and unsaturated monomers can be effectively initiated to polymerize under the radiation of a UV lamp; in addition, the solvent property in the resin and oligomer is good.
The photoinitiator is preferably one of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetraphenylimidazole, 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine and 4-benzoyl-4' -methyl diphenyl sulfide. The photoinitiator can greatly reduce the curing shrinkage rate of the pressure-sensitive adhesive while improving the photo-initiation efficiency, and the photo-curing efficiency of the pressure-sensitive adhesive is higher by matching with the action of the light guide filler.
The light guide filler is one of nano zinc oxide, nano titanium dioxide, polymethyl methacrylate micro powder and nano aluminum oxide with the particle size of 20-30 nm. The light guide filler has an extinction effect, has a smooth hand feeling, cannot absorb UV (ultraviolet), does not influence the absorption energy of a photoinitiator, simultaneously keeps transparent texture, has good heat resistance and dispersibility, and provides an excellent optical diffusion effect and a good high-refractive-index transparent brightness performance.
The magnetic conductive filler is one of nano iron powder, nickel powder, carbonyl iron powder, iron oxide and iron-based alloy powder with the particle size of 20-30 nm. The iron-based alloy powder can be a composite powder of iron and particles of nickel, silver and the like, and can also be a composite powder of iron oxide and particles of nickel, silver and the like. Magnetically conductive fillers are available by atomization techniques that achieve atomization of a molten metal stream into a liquid or gaseous medium, the essence of atomization being to melt a substantial volume of the precursor and to eject a substantial portion of the molten metal droplets into a gaseous or liquid environment.
The modified functional resin contains 100-118 terminal hydroxyl groups, and can be synthesized by the following steps:
s1, adding 1 part of 3-methylpentane-2, 4-diol and 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid into a closed container according to a molar ratio under the protection of inert gas and stirring, then adding concentrated sulfuric acid as a catalyst, stirring at 160-180 ℃ for 1-2 hours to perform condensation reaction, and obtaining a matrix A1 of the modified functional resin;
s2, adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A1 obtained in the step S1, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A2 of modified functional resin; adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A2, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A3 of modified functional resin; repeating the step 4 times until a matrix A7 of the modified functional resin is obtained;
s3, washing the matrix A7 of the modified functional resin obtained in the step S2, transferring the washed matrix A into a container, adding acrylic acid and 1, 4-benzenediol, stirring and reacting for 4 hours at 80 ℃, and washing the product to obtain the modified functional resin.
The modified functional resin has abundant terminal hydroxyl groups, is easy to react with other groups, and improves the crosslinking density of a product, so that the cohesive strength and the heat resistance are improved, and therefore, the adhesive is endowed with excellent anti-migration property, and components in the pressure-sensitive adhesive cannot migrate to the surface of an adhered material. The pressure-sensitive adhesive is added with the modified functional resin, so that the possibility of photochemical reaction can be eliminated or slowed down, and the photoaging process can be prevented or delayed; the modified functional resin has good compatibility with the main resin and good storage stability, and does not influence the interface performance of the pressure-sensitive adhesive.
The rheological additive can adjust the flowing characteristic of the pressure-sensitive adhesive resin, the molecular weight is between 7500-15000 g/mol, the molecules of the rheological additive are associated with each other to form a ring-shaped micelle along with the increase of the concentration, the hydrophobic component in the molecules faces to the inside of the micelle, and the hydrophilic middle chain segment forms an outer ring-shaped shell, so that the rheological characteristic of the pressure-sensitive adhesive can be changed by changing the concentration of the rheological additive.
The flatting agent is one or more selected from polyethylacrylate, polybutylacrylate, polyacrylic acid 2-ethylhexyl ester and polyethylacrylate. The leveling agent is beneficial to the dispersion of the filler, is beneficial to improving the light guide property and the magnetic conductivity, and plays a synergistic role.
The dispersing agent is one or more of sodium hydroxypropyl acrylate, sodium carboxyethyl benzoate and sodium dimethyl cellulose tannate.
The defoaming agent is one or more of epoxy pentane alcohol benzoate, nitro heptane laurate, dimethyl butyl alcohol isopropyl dioleate and isobutyl octadecanol diethyl titanate.
The coupling agent is one or more of isobutyl vinyl dimethyl siloxane, propenyl butanone dichloro siloxane, isobutyl mercaptopropyl dimethyl ketoxime group siloxane and dimethyl dichlorosilane.
A method for preparing the photocuring magnetic guide photosensitive pressure-sensitive adhesive comprises the following steps:
s1, firstly adding a certain amount of aliphatic epoxy modified acrylate resin and functional monomers into a reaction device provided with a stirring device, a reflux condensing device, a dripping device, a thermometer and a nitrogen introducing device, heating to 80 ℃, then adding a photoinitiator, a chain transfer agent and a defoaming agent which account for 5-10% of the total amount of the formula, carrying out polymerization reaction for 0.5h, then slowly dripping a leveling agent, a dispersing agent and the rest of the photoinitiator, the chain transfer agent and the defoaming agent, finishing dripping within 2h, maintaining the reflux state all the time in the dripping process, gradually increasing the temperature, after finishing dripping, adding a certain amount of modified functional resin, carrying out reflux reaction for 0.5h, stopping the reaction, and cooling to obtain a prepolymer;
s2, mixing absolute ethyl alcohol, rheological additive and coupling agent according to a specified proportion, taking the mixture as a diluent to dilute the prepolymer to a proper viscosity, adding magnetic conductive filler and light guide filler, and uniformly mixing to obtain the photocuring magnetic conductive photosensitive pressure-sensitive adhesive.
A preparation method of a photocuring magnetic conduction and light conduction pressure-sensitive adhesive tape comprises the steps of coating the photocuring magnetic conduction and light conduction pressure-sensitive adhesive on a release film, drying at 120 ℃ for 10min, and then placing the release film under an ultraviolet lamp for radiation crosslinking at a distance of 15cm to obtain the photocuring magnetic conduction and light conduction pressure-sensitive adhesive tape, which can be used for material surface sticking and is equivalent to a use method of a double-sided adhesive tape. The UV light source is preferably a light source generated by a carbon arc lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a fluorescent lamp, a hernia lamp and the like, and the light source intensity, the emission stability and the light splitting energy distribution uniformity are good.
The composition ratios of the components of examples 1-3 are shown in Table 1.
TABLE 1 component formulations of examples 1-3
Example 1
The functional monomer is N-methacrylamide, the tackifying resin is terpene resin, the diluent is ethanol, the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone, the light guide filler is nano titanium dioxide, the magnetic conductive filler is nano iron powder, the leveling agent is polybutyl acrylate, the dispersing agent is sodium hydroxypropyl acrylate, the coupling agent is propenyl butyryl dichlorosiloxane, and the defoaming agent is epoxy pentane alcohol benzoate.
Example 2
The functional monomer is N-hydroxyethyl acrylamide, the tackifying resin is petroleum resin, the diluent is ethanol + HDDA, the photoinitiator is 2,2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetraphenyl-1, 2' -biimidazole, the light guide filler is nano zinc oxide, the magnetic conductive filler is nano carbonyl iron powder, the leveling agent is polyethylacrylate, the dispersing agent is sodium carboxyethyl benzoate, the coupling agent is isobutyl vinyl dimethyl siloxane, and the defoaming agent is lauric acid nitroheptanol ester.
Example 3
The functional monomer is N-methacrylamide, the tackifying resin is terpene resin, the diluent is ethanol + HDDA, the photoinitiator is 4-benzoyl-4' -methyl diphenyl sulfide, the light guide filler is nano aluminum oxide, the magnetic conductive filler is nano iron-silver composite powder, the leveling agent is polyacrylic acid 2-ethylhexyl ester, the dispersing agent is sodium hydroxypropyl acrylate, the coupling agent is propenyl butyryl dichlorosiloxane, and the defoaming agent is isopropyl dimethyl butyl dioleate.
1. Adhesion Performance test
The photo-curable magnetic and light conductive pressure sensitive adhesive tape obtained above was tested for 180 ° peel force by test method ASTM D3132, for initial adhesion by test method ASTM D3330, and for holding adhesion by test method ASTM D3654, and accordingly, 2 parts of a common commercially available adhesive tape was used as comparative example 1-2, and three force performance tests were carried out under the same conditions, and the results are shown in table 2.
TABLE 2 results of adhesion Performance test of examples 1-2 and comparative examples 1-2
2. Testing of light guide performance
The light guiding properties were obtained by testing the light transmittance thereof as shown in table 3.
Table 3 light guide performance test results of examples 1 to 3 and comparative example 1
| Serial number | Example 1 | Example 2 | Example 3 | Comparative example 1 |
| Light transmittance | 90 | 91 | 91 | 78 |
Therefore, the photocuring magnetic-conductive light-guide adhesive tape prepared by the invention has better adhesive property and optical property, and can be applied to the industry of electronic components. The above detailed description is specific to possible embodiments of the present invention, and the embodiments are not intended to limit the scope of the present invention, and all equivalent implementations or modifications that do not depart from the scope of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. The photocuring magnetic guide photosensitive pressure-sensitive adhesive is characterized by comprising the following components in parts by weight: 30-40 parts of modified functional resin, 60-80 parts of aliphatic epoxy modified acrylate resin, 5-15 parts of functional monomer, 10-30 parts of diluent, 0.5-1 part of photoinitiator, 5-10 parts of light guide filler, 8-12 parts of magnetic conductive filler, 1-3 parts of rheological additive, 0.5-1.8 parts of flatting agent, 1-2.5 parts of dispersing agent, 0.8-2.4 parts of coupling agent, 1-3 parts of defoaming agent and 0.2-1 part of chain transfer agent.
2. The photocuring magnetic-guiding photosensitive pressure-sensitive adhesive according to claim 1, further comprising 20-50 parts of a tackifying resin, wherein the tackifying resin is terpene resin or petroleum resin.
3. The photocuring magnetic guide and light pressure-sensitive adhesive as claimed in claim 1, wherein the aliphatic epoxy modified acrylate resin is a colorless transparent liquid, has a molecular weight of 5000-20000 and a viscosity of 5000-20000 mPa-s at 25 ℃, is prepared from alkyl epoxy resin, acrylic acid, butyl acrylate and isooctyl acrylate, and is prepared by reacting acrylic acid with the alkyl epoxy resin and then polymerizing the grafted product with the butyl acrylate and the isooctyl acrylate.
4. The photocurable magnetically and magnetically conductive photosensitive adhesive according to claim 1, wherein the functional monomer is a polar monomer containing N atoms, and the polar monomer containing N atoms is one or two of N-methylacrylamide, N-ethylacrylamide, N-methylolacrylamide, N-hydroxyethylacrylamide, diacetone acrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-ethyl-N-aminoethylacrylamide, N-ethyl-N-hydroxyethylacrylamide, N-dimethylolacrylamide, N-diethylolacrylamide, N-vinylpyrrolidone, N-vinylcaprolactam; the diluent is ethanol or/and 1, 6-hexanediol diacrylate (HDDA).
5. The photo-curing magnetic and conductive photosensitive pressure-sensitive adhesive according to claim 1, wherein the photo-initiator is one selected from 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyl-1, 2 ' -biimidazole, 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, and 4-benzoyl-4 ' -methyldiphenyl sulfide.
6. The photocuring magnetic guide and light pressure-sensitive adhesive as claimed in claim 1, wherein the light guide filler is one of nano zinc oxide, nano titanium dioxide, polymethyl methacrylate micro powder and nano aluminum oxide with the particle size of 20-30 nm; the magnetic conductive filler is one of nano iron powder, nickel powder, carbonyl iron powder, iron oxide and iron-based alloy powder with the particle size of 20-30 nm.
7. The photocuring magnetic guide and guide photosensitive pressure-sensitive adhesive as claimed in claim 1, wherein the modified functional resin contains 100 to 118 terminal hydroxyl groups, and is synthesized by the following steps:
s1, adding 1 part of 3-methylpentane-2, 4-diol and 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid into a closed container according to a molar ratio under the protection of inert gas and stirring, then adding concentrated sulfuric acid as a catalyst, stirring at 160-180 ℃ for 1-2 hours to perform condensation reaction, and obtaining a matrix A1 of the modified functional resin;
s2, adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A1 obtained in the step S1, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A2 of modified functional resin; adding 2 parts of 3, 5-dihydroxycyclohexanecarboxylic acid and concentrated sulfuric acid into the matrix A2, and stirring at 160-180 ℃ for 1-2 hours to obtain a matrix A3 of modified functional resin; repeating the step 4 times until a matrix A7 of the modified functional resin is obtained;
s3, washing the matrix A7 of the modified functional resin obtained in the step S2, transferring the washed matrix A into a container, adding acrylic acid and 1, 4-benzenediol, stirring and reacting for 4 hours at 80 ℃, and washing the product to obtain the modified functional resin.
8. The photo-curing magnetic guide and guide photo-pressure sensitive adhesive as claimed in claim 1, wherein the leveling agent is one or more selected from polyethylacrylate, polybutylacrylate, poly-2-ethylhexyl acrylate and polyethylacrylate; the dispersing agent is one or more of sodium hydroxypropyl acrylate, sodium carboxyethyl benzoate and sodium dimethyl cellulose tannate; one or more of epoxy pentane alcohol benzoate, nitro heptyl laurate, dimethyl butyl isopropyl dioleate and isobutyl stearyl diethyl titanate in the defoaming agent; the coupling agent is one or more of isobutyl vinyl dimethyl siloxane, propenyl butanone dichloro siloxane, isobutyl mercaptopropyl dimethyl ketoxime group siloxane and dimethyl dichlorosilane.
9. A method for preparing the photocuring magnetic guide and guide photosensitive pressure-sensitive adhesive as claimed in any one of claims 1 to 8, which comprises the following steps:
s1, firstly adding a certain amount of aliphatic epoxy modified acrylate resin and functional monomers into a reaction device provided with a stirring device, a reflux condensing device, a dripping device, a thermometer and a nitrogen introducing device, heating to 80 ℃, then adding a photoinitiator, a chain transfer agent and a defoaming agent which account for 5-10% of the total amount of the formula, carrying out polymerization reaction for 0.5h, then slowly dripping a leveling agent, a dispersing agent and the rest of the photoinitiator, the chain transfer agent and the defoaming agent, finishing dripping within 2h, maintaining the reflux state all the time in the dripping process, gradually increasing the temperature, after finishing dripping, adding a certain amount of modified functional resin, carrying out reflux reaction for 0.5h, stopping the reaction, and cooling to obtain a prepolymer;
s2, mixing the diluent, the rheological additive and the coupling agent according to the specified proportion, adding the mixture into the prepolymer for diluting to the appropriate viscosity, adding the magnetic conductive filler and the light guide filler, and uniformly mixing to obtain the photocuring magnetic conductive light pressure-sensitive adhesive.
10. A preparation method of a photocuring magnetic-conductive light-conductive pressure-sensitive adhesive tape is characterized in that the photocuring magnetic-conductive light-conductive pressure-sensitive adhesive as defined in any one of claims 1 to 8 is coated on a release film, dried at 120 ℃ for 10min and then placed under an ultraviolet lamp for radiation crosslinking at a distance of 15cm, and the photocuring magnetic-conductive light-conductive pressure-sensitive adhesive tape is obtained.
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| CN115803407B (en) * | 2021-03-22 | 2023-06-23 | 积水化学工业株式会社 | Adhesive tape, method for fixing electronic device component or in-vehicle device component, and method for manufacturing electronic device or in-vehicle device |
| US11802224B2 (en) | 2021-03-22 | 2023-10-31 | Sekisui Chemical Co., Ltd. | Adhesive tape, method for fixing electronic device component or on-board device component, and method for producing electronic device or on-board device |
| US11912905B2 (en) | 2021-03-22 | 2024-02-27 | Sekisui Chemical Co., Ltd. | Adhesive tape, method for immobilizing electronic device component or on-vehicle device component, method for manufacturing electronic device or on-vehicle device |
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