CN114958209A - Ultraviolet curing adhesive with delayed curing function and preparation method thereof - Google Patents
Ultraviolet curing adhesive with delayed curing function and preparation method thereof Download PDFInfo
- Publication number
- CN114958209A CN114958209A CN202210572953.XA CN202210572953A CN114958209A CN 114958209 A CN114958209 A CN 114958209A CN 202210572953 A CN202210572953 A CN 202210572953A CN 114958209 A CN114958209 A CN 114958209A
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- CN
- China
- Prior art keywords
- rosin
- aziridine
- borate
- resin
- diisocyanate
- 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.)
- Granted
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- 239000000853 adhesive Substances 0.000 title claims abstract description 42
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 42
- 230000003111 delayed effect Effects 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims description 7
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 36
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 36
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 150000001541 aziridines Chemical class 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 17
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 239000003381 stabilizer Substances 0.000 claims abstract description 7
- 239000012949 free radical photoinitiator Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims description 23
- 238000004806 packaging method and process Methods 0.000 claims description 11
- 238000007789 sealing Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 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 description 10
- 150000002009 diols Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 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 7
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 7
- 238000005303 weighing Methods 0.000 claims description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 6
- DTEAMMSJXLXUOQ-UHFFFAOYSA-N 1-hydroxyaziridine Chemical compound ON1CC1 DTEAMMSJXLXUOQ-UHFFFAOYSA-N 0.000 claims description 5
- -1 4-methylmercaptophenyl Chemical group 0.000 claims description 5
- 125000004069 aziridinyl group Chemical group 0.000 claims description 5
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 5
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZEJWZIZFOBFKOC-UHFFFAOYSA-N 1-(aziridin-1-yl)ethanol Chemical compound CC(O)N1CC1 ZEJWZIZFOBFKOC-UHFFFAOYSA-N 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 claims description 3
- HJVAFZMYQQSPHF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;boric acid Chemical compound OB(O)O.OCCN(CCO)CCO HJVAFZMYQQSPHF-UHFFFAOYSA-N 0.000 claims description 2
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 claims description 2
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 claims description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 claims description 2
- HWJYGSDXNANCJM-UHFFFAOYSA-N tridodecyl borate Chemical compound CCCCCCCCCCCCOB(OCCCCCCCCCCCC)OCCCCCCCCCCCC HWJYGSDXNANCJM-UHFFFAOYSA-N 0.000 claims description 2
- WZGVRXXJKGXOBR-UHFFFAOYSA-N trihexadecyl borate Chemical compound CCCCCCCCCCCCCCCCOB(OCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCC WZGVRXXJKGXOBR-UHFFFAOYSA-N 0.000 claims description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 2
- GZKLCETYSGSMRA-UHFFFAOYSA-N trioctadecyl borate Chemical compound CCCCCCCCCCCCCCCCCCOB(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC GZKLCETYSGSMRA-UHFFFAOYSA-N 0.000 claims description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims description 2
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 claims description 2
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 claims description 2
- FYAMVEZOQXNCIE-UHFFFAOYSA-N tris(3-methylphenyl) borate Chemical compound CC1=CC=CC(OB(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 FYAMVEZOQXNCIE-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 38
- 238000002156 mixing Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000005336 cracking Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OQILSTRGJVCFAG-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)butan-1-ol Chemical compound CCCC(O)OCC1CO1 OQILSTRGJVCFAG-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical compound CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6492—Lignin containing materials; Wood resins; Wood tars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses an ultraviolet curing adhesive with a delayed curing function, which is prepared from the following raw materials in percentage by weight: 40-70% of rosin modified aziridine resin, 15-35% of acrylate monomer, 10-30% of rosin modified acrylate resin, 0.3-6% of free radical photoinitiator, 0.1-5% of photoacid generator and 0.01-1% of stabilizer. The ultraviolet curing adhesive has the function of delayed curing, can be used in lightproof application scenes, solves the problem that the conventional UV adhesive is limited by the light transmittance of materials, and has the advantages of excellent performance of cured materials, high bonding reliability and wide application range.
Description
Technical Field
The invention belongs to the field of photocuring materials, and relates to an ultraviolet curing adhesive with a delayed curing function and a preparation method thereof.
Background
The photocuring material is widely researched due to a plurality of outstanding advantages of high curing speed, environmental friendliness, low energy consumption, no solvent volatilization and the like, and is rapidly popularized in various industries. However, the ultraviolet light curing adhesive has its own limitation, and the conventional ultraviolet light curing adhesive can only be used in the bonding application of the light-transmitting material, but in the bonding occasion of the light-proof material, because the material is light-proof, the ultraviolet light curing adhesive can not be cured, and the ultraviolet light curing adhesive has obvious limitation in the actual application; the ultraviolet curing adhesive has the function of delayed curing, can be used in an opaque application scene, and solves the problem that the conventional UV adhesive is limited by the light transmittance of materials.
Disclosure of Invention
The invention provides an ultraviolet curing adhesive with a delay function and a preparation method thereof, aiming at solving the problem that the ultraviolet curing adhesive can not be cured in an opaque material in the prior art, so that the cured product of the ultraviolet curing adhesive has the delay curing function and can be applied to the bonding of the opaque material.
The technical scheme for solving the technical problems is as follows:
an ultraviolet curing adhesive with a delayed curing function is composed of the following raw materials in percentage by weight: 40-70% of rosin modified aziridine resin, 15-35% of acrylate monomer, 10-30% of rosin modified acrylate resin, 0.3-6% of free radical photoinitiator, 0.1-5% of photoacid generator and 0.01-1% of stabilizer.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the rosin-modified aziridine resin refers to a rosin-modified aziridine resin containing an aziridine reactive group synthesized from rosin diol, diisocyanate and hydroxy aziridine, the rosin diol being a diol having two hydroxyl groups and having a fundamental rosin acid structure, the diisocyanate comprising: toluene Diisocyanate (TDI), isophorone diisocyanate (IPDI), diphenylmethane diisocyanate (MDI) or Hexamethylene Diisocyanate (HDI), and the like, and any mixture thereof. The hydroxy aziridine refers to a compound having both a hydroxyl group and an aziridine group, such as 1-hydroxyethyl aziridine (cas: 1072-52-2). A rosin-modified aziridine resin, the structural formula of which is represented by the following general formula (i):
the synthesis method comprises the following steps: 200g of rosin diol, 11.6g of toluene diisocyanate and 0.01g of dibutyltin dilaurate serving as a catalyst are added into a three-neck flask with a thermometer, the temperature is increased to 65 ℃, the temperature is controlled to be 70-75 ℃, and the reaction lasts for 2-3 h; then adding 3.2g of 1-hydroxyethyl aziridine (1072-52-2), controlling the temperature at 70-75 ℃ and reacting for 2-3 h; analyzing NCO groups by an infrared spectrometer, and stopping heating reaction when NCO peaks disappear completely to obtain the rosin modified aziridine resin, wherein the reaction formula is as follows:
further, the acrylate monomer is a monofunctional acrylate monomer or a mixture of two or more functional acrylate monomers, and comprises one or a mixture of any more of tetrahydrofuran acrylate (THFA), isooctyl methacrylate (ISOA), lauryl methacrylate (LA), isobornyl methacrylate (IBOA), N-Dimethylacrylamide (DMAA) and 1, 6-hexanediol diacrylate (HDDA).
Further, the molecular structural formula of the rosin modified acrylate resin is as follows:
further, the radical photoinitiator was trade name 1173 (2-hydroxy-2-methyl-1-phenylacetone), 184 (1-hydroxycyclohexyl benzophenone), 907 (2-methyl-1- (4-methylmercaptophenyl) -2-morpholine-1-propanone), 369 (2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone), 819 (bis (2,4, 6-trimethylbenzoyl) phenylphosphorus oxide), 651 (alpha, alpha' -dimethylbenzylketal), ITX (isopropylthioxanthone), BP (benzophenone), OMBB (methyl o-benzoylbenzoate) and TPO (2,4, 6-trimethylbenzoyldiphenylphosphine oxide).
Further, the photoacid generator includes sulfonium and iodonium cationic photoinitiators, which can generate ultra-strong protonic acids upon UV illumination. For example: IRGACURE 250 from BASF, WPI-113, WPI-116 and WPI-124 from Fujifilm, Japan.
Further, the stabilizer in the synthesis method is one or a mixture of more of boric acid ester, aluminum chelate and organic acid, and comprises trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, dodecyl borate, trihexadecyl borate, trioctadecyl borate, tri-o-tolyl borate, tri-m-tolyl borate, triethanolamine borate, barbituric acid and the like.
The preparation method of the ultraviolet curing adhesive with the delayed curing function comprises the following steps: weighing 40-70% of rosin modified aziridine resin, 15-35% of acrylate monomer, 10-30% of rosin modified acrylate resin, 0.3-6% of free radical photoinitiator, 0.1-5% of photoacid generator and 0.01-1% of stabilizer, sequentially adding the materials into a stirrer, vacuumizing until the vacuum degree is-0.08 to-0.05 MPa, stirring at 500-1000 rpm for 0.5-2 hours, uniformly stirring, naturally airing to room temperature, sealing and packaging.
The invention has the beneficial effects that: according to the ultraviolet light curing adhesive prepared by the invention, the mechanism that aziridine reacts under the catalysis of acid is utilized, when a photoacid generator in the formula is irradiated by UV, super-strong proton acid is generated, the super-strong proton acid catalyzes aziridine to carry out polymerization reaction, and the polymerization reaction of the aziridine catalyzed by the acid is not instantaneous unlike the instantaneous reaction of free radical polymerization of acrylic ester, so that the formula has the reaction characteristic of UV delayed curing; according to the invention, by molecular structure design, aziridine groups are introduced into a macromolecular chain of rosin ester to synthesize rosin modified aziridine resin, and the resin containing a rosin structure has better adhesive force to a base material; the ultraviolet curing adhesive obtained by the invention not only has the function of delayed curing and can meet the bonding occasion of opaque materials, but also has the advantages of high adhesive force to a base material, excellent performance of cured materials and high bonding reliability, and can be widely applied to high-end electronic packaging industry.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Synthetic examples
The synthetic method of the rosin modified aziridine resin comprises the following steps: 200g of rosin diol, 11.6g of toluene diisocyanate and 0.01g of dibutyltin dilaurate serving as a catalyst are added into a three-neck flask with a thermometer, the temperature is increased to 65 ℃, the temperature is controlled to be 70-75 ℃, and the reaction lasts for 2-3 h; then adding 3.2g of hydroxy aziridine (1072-52-2), controlling the temperature at 70-75 ℃ and reacting for 2-3 h; and analyzing NCO groups by using an infrared spectrometer, and stopping heating reaction when an NCO peak disappears completely to obtain the rosin modified aziridine resin.
Example 1
The following raw materials, namely 55g of rosin modified aziridine resin, 20g of THFA, 21g of rosin modified acrylate resin, 1842 g of photoinitiator, 0.5g of photoinitiator TPO, 2502 g of photoacid generator IRGACURE and 0.6g of triethyl borate are accurately weighed; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.08 MPa, stirring at 500 rpm for 2 hours, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Example 2
Accurately weighing 45g of rosin modified aziridine resin, 30g of IBOA, 26g of rosin modified acrylate resin, 1843 g of photoinitiator, 1.1g of photoinitiator TPO, 2501.5 g of photoacid generator IRGACURE and 0.3g of barbituric acid; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.05 MPa, stirring at 750 revolutions per minute for 1 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Example 3
The preparation method comprises the following steps of accurately weighing 67g of rosin modified aziridine resin, 15g of IBOA, 14g of rosin modified acrylate resin, 6513 g of photoinitiator, 1.1g of photoinitiator TPO, WPI-1165 g of photoacid generator and 0.06g of barbituric acid; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.06 MPa, stirring at 700 rpm for 1.5 hours, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Example 4
The following raw materials, namely 58g of rosin modified aziridine resin, 29g of LA, 11g of rosin modified acrylate resin, 1842 g of photoinitiator, 1.5g of photoinitiator TPO, 2501.9 g of photoacid generator IRGACURE and 0.16g of barbituric acid, are accurately weighed; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.07 MPa, stirring at 800 rpm for 1 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Example 5
The following raw materials, 65g of rosin modified aziridine resin, 10g of THFA, 13g of IBOA, 21g of rosin modified acrylate resin, 6512 g of photoinitiator, 0.5g of photoinitiator TPO, 0.29g of photoacid generator WPI-1242.3 and 0.29g of boric acid tri-m-toluate, are accurately weighed; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.08 MPa, stirring at 1000 rpm for 0.5 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Comparative example 1
Accurately weighing the following raw materials, namely CN966J75 of Saedoma company, 55 g; LA, 48 g; photoinitiator 1173, 2 g; photoinitiator TPO, 1 g; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.08 MPa, stirring at 500 rpm for 2 hours, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Comparative example 2
Accurately weighing 6127 g of Changxing chemical raw materials and 42g of Changxing chemical raw materials; IBOA, 51 g; photoinitiator 651, 3 g; photoinitiator TPO, 1 g; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.05 MPa, stirring at 750 revolutions per minute for 1 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Comparative example 3
The following raw materials, namely 60g of bisphenol A epoxy resin, 5g of polycaprolactone polyol, 1g of cationic curing agent, 1g of 1173 photoinitiator, 2g of butanediol glycidyl ether, 0.01g of isopropyl thioxanthone, 0.1g of polyethyleneimine modified graphene oxide and 1g of gas phase silicon thixotropic agent are accurately weighed; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.05 MPa, stirring at 750 revolutions per minute for 1 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
Comparative example 4
Accurately weighing 0.2g of photobase generator and 7.73g of bisphenol A type epoxy resin (E51), mixing, stirring at 110 ℃ until the mixture is clear and transparent, and cooling to room temperature; 4.23g of bisphenol A Epoxy Acrylate (EA), 1.94g of 1, 6-hexanediol diacrylate (HDDA), 8.2g of pentaerythritol tetra-3-mercaptopropionate (SH4), 0.1g of photosensitizer 2-Isopropylthioxanthone (ITX) and 0.1g of free radical inhibitor 2, 2, 6, 6-tetramethylpiperidine-1-oxyl free radical (TEMPO) are added into the system; sequentially adding the components into a double-planetary power mixing stirrer, vacuumizing to the vacuum degree of-0.05 MPa, stirring at 750 revolutions per minute for 1 hour, uniformly stirring, naturally airing to room temperature to obtain the ultraviolet curing adhesive, and sealing and packaging.
The performance of an ultraviolet light curing adhesive having a delayed curing function according to the present invention was tested by the following tests.
Test examples Performance test
Conformable time test: dispensing on a black substrate, activating by UV light, standing for different times, and then attaching an aluminum sheet, wherein if the cohesive strength of pectin is too high, the aluminum sheet cannot be attached, and the longest time that the aluminum sheet can be attached is the attachable time according to tests.
UV activated curing conditions: light intensity of 50mW/cm 2 Illumination time 10 s;
shear strength: substrate black PC + aluminum.
And (3) drop performance testing: height 1.8m, fall 50 times, judge whether to split.
The test results are shown in table 1:
TABLE 1 comparative test results of the samples prepared in examples 1-5 with those of a conventional UV-curable adhesive
| Test specimen | After UV activation, the time of application is long | Shear strength at 30min | Shear strength at 60min | Shear strength at 24h | Elongation% | Drop performance |
| Sample of example 1 | 6min | 1.3MPa | 2.4MPa | 9.2MPa | 346 | Without cracking |
| Sample of example 2 | 11min | 0.6MPa | 1.3MPa | 11.5MPa | 325 | Without cracking |
| Sample of example 3 | 4min | 2.3MPa | 3.7MPa | 12.3MPa | 343 | Without cracking |
| Sample of example 4 | 7min | 1.1MPa | 2.3MPa | 7.3MPa | 329 | Without cracking |
| Sample of example 5 | 9min | 0.9MPa | 1.8MPa | 11.8MPa | 311 | Without cracking |
| Sample of comparative example 1 | Failure to conform after UV activation | - | - | - | - | - |
| Sample of comparative example 2 | UV activationCannot be adhered | - | - | - | - | - |
| Sample of comparative example 3 | 8min | 0.9MPa | 1.9MPa | 23MPa | 208 | Cracking of |
| Sample of comparative example 4 | 23min | 0.1MPa | 0.4MPa | 1.2MPa | 89 | Cracking of |
From the results, compared with the existing common light-cured adhesive, the ultraviolet light-cured adhesive with the delayed curing function has the delayed curing function, has good adhesive force to the base material, has larger elongation and better dropping performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (7)
1. An ultraviolet curing adhesive with a delayed curing function is composed of the following raw materials in percentage by weight: 40-70% of rosin modified aziridine resin, 15-35% of acrylate monomer, 10-30% of rosin modified acrylate resin, 0.3-6% of free radical photoinitiator, 0.1-5% of photoacid generator and 0.01-1% of stabilizer.
2. The UV-curable adhesive with a delayed curing function according to claim 1, wherein the rosin-modified aziridine resin is a rosin-modified aziridine resin containing an aziridine reactive group synthesized from rosin diol, diisocyanate and hydroxy aziridine; the rosin diol is dihydric alcohol which contains two hydroxyl groups and has a fundamental structure of rosin acid; the diisocyanate comprises one or a mixture of any more of toluene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate or hexamethylene diisocyanate; the hydroxy aziridine is a compound containing both hydroxy and aziridine groups, and the structural formula of the rosin modified aziridine resin is represented by the following general formula (I):
the synthesis method comprises the following steps: 200g of rosin diol, 11.6g of toluene diisocyanate and 0.01g of dibutyltin dilaurate serving as a catalyst are added into a three-neck flask with a thermometer, the temperature is increased to 65 ℃, the temperature is controlled to be 70-75 ℃, and the reaction lasts for 2-3 h; then adding 3.2g of 1-hydroxyethyl aziridine, controlling the temperature at 70-75 ℃ and reacting for 2-3 h; analyzing NCO groups by an infrared spectrometer, and stopping heating reaction when NCO peaks disappear completely to obtain the rosin modified aziridine resin, wherein the reaction formula is as follows:
3. the UV-curable adhesive with a delayed curing function according to claim 1, wherein the acrylate monomer is one or a mixture of any several of tetrahydrofuran acrylate, isooctyl methacrylate, lauryl methacrylate, isobornyl methacrylate, N-dimethylacrylamide and 1, 6-hexanediol diacrylate, and the rosin-modified acrylate resin has a molecular structural formula as follows:
4. the UV-curable adhesive with delayed curing function according to claim 1, the free radical photoinitiator is one or a mixture of any more of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl benzophenone, 2-methyl-1- (4-methylmercaptophenyl) -2-morpholine-1-acetone, 2-benzyl-2-dimethylamino-1- (4-morpholine phenyl) -1-butanone, bis (2,4, 6-trimethyl benzoyl) phenyl phosphorus oxide, alpha' -dimethyl benzil ketal, isopropyl thioxanthone, benzophenone, methyl o-benzoylbenzoate and 2,4, 6-trimethyl benzoyl diphenyl phosphorus oxide.
5. The UV-curable adhesive having a delayed curing function according to claim 1, wherein the photoacid generator is IRGACURE 250 manufactured by BASF corporation, WPI-113, WPI-116 and WPI-124 manufactured by Fujifilm corporation, Japan.
6. The UV-curable adhesive with delayed curing function according to claim 1, wherein the stabilizer is one or more selected from trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, dodecyl borate, trihexadecyl borate, trioctadecyl borate, tri-o-tolyl borate, tri-m-tolyl borate, triethanolamine borate, barbituric acid, etc.
7. The UV-curable adhesive with delayed curing function according to claim 1, wherein the preparation method comprises: weighing 40-70% of rosin modified aziridine resin, 15-35% of acrylate monomer, 10-30% of rosin modified acrylate resin, 0.3-6% of free radical photoinitiator, 0.1-5% of photoacid generator and 0.01-1% of stabilizer, sequentially adding the materials into a stirrer, vacuumizing until the vacuum degree is-0.08 to-0.05 MPa, stirring at 500-1000 rpm for 0.5-2 hours, uniformly stirring, naturally airing to room temperature, sealing and packaging.
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| PCT/CN2023/083241 WO2023226568A1 (en) | 2022-05-25 | 2023-03-23 | Ultraviolet-curing adhesive having curing delaying function, and preparation method therefor |
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