CN117143540A - UV tackifying optical adhesive film for glass bonding and preparation method thereof - Google Patents
UV tackifying optical adhesive film for glass bonding and preparation method thereof Download PDFInfo
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- CN117143540A CN117143540A CN202310874438.1A CN202310874438A CN117143540A CN 117143540 A CN117143540 A CN 117143540A CN 202310874438 A CN202310874438 A CN 202310874438A CN 117143540 A CN117143540 A CN 117143540A
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- Prior art keywords
- tackifying
- parts
- optical adhesive
- epoxy
- adhesive film
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- 230000003287 optical effect Effects 0.000 title claims abstract description 59
- 239000002313 adhesive film Substances 0.000 title claims abstract description 42
- 239000011521 glass Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000004593 Epoxy Substances 0.000 claims abstract description 58
- 230000001070 adhesive effect Effects 0.000 claims abstract description 38
- 239000000853 adhesive Substances 0.000 claims abstract description 36
- 239000003822 epoxy resin Substances 0.000 claims abstract description 27
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 27
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 18
- 239000003085 diluting agent Substances 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 17
- 239000011248 coating agent Substances 0.000 claims abstract description 16
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- -1 sulfonium hexafluoroantimonate Chemical compound 0.000 claims description 21
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 12
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000007822 coupling agent Substances 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 7
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002318 adhesion promoter Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- JDJCWTMAUWZTOM-UHFFFAOYSA-N 2,2-bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl)hexanedioic acid Chemical compound C1CC2OC2CC1CC(C(O)=O)(CCCC(=O)O)CC1CC2OC2CC1 JDJCWTMAUWZTOM-UHFFFAOYSA-N 0.000 claims description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 3
- LQZDDWKUQKQXGC-UHFFFAOYSA-N 2-(2-methylprop-2-enoxymethyl)oxirane Chemical compound CC(=C)COCC1CO1 LQZDDWKUQKQXGC-UHFFFAOYSA-N 0.000 claims description 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 3
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 claims description 3
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 3
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 3
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 claims 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims 2
- 239000013530 defoamer Substances 0.000 claims 1
- 239000012788 optical film Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 230000007774 longterm Effects 0.000 abstract description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- NCXOIRPOXSUZHL-UHFFFAOYSA-N [Si].[Ca].[Na] Chemical compound [Si].[Ca].[Na] NCXOIRPOXSUZHL-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a UV tackifying optical adhesive film for glass bonding and a preparation method thereof, wherein the adhesive film is obtained by coating and curing the UV tackifying optical adhesive, and the UV tackifying optical adhesive comprises the following raw material components in parts by weight: 30-50 parts of epoxy acrylic copolymer; 40-60 parts of epoxy resin; 5-15 parts of a diluent; 1-5 parts of a photoinitiator; 0.5-4 parts of auxiliary agent. The adhesive film has higher initial adhesion strength to a base material, and can ensure a positioning effect; after positioning, the adhesive film can be further crosslinked and hardened under certain UV irradiation, the bonding capability of the hardened adhesive film to the base material is greatly improved, and meanwhile, the modulus and the strength of the adhesive film are also greatly improved, so that the bonding effect is ensured, the long-term use resistance is improved, and the adhesive film can be well applied to bonding of planar electronic glass.
Description
Technical Field
The invention relates to the field of optical adhesive materials, in particular to a UV tackifying optical adhesive film for glass adhesion and a preparation method thereof.
Background
With the technical development of consumer electronics, the requirements of consumers on beauty and durability are improved, and the application development of electronic glass in the fields of electronic products such as mobile phones, computers, televisions, vehicle-mounted and wearable equipment and the like is promoted. Because the glass has the advantages of good light transmittance, high strength, good toughness, scratch resistance, wear resistance, attractive appearance and the like.
The electronic glass generally adopts a multi-layer bonding and composite structure to meet the use requirements, and is sodium-calcium-silicon glass or alkali-aluminum silicate glass, so that the surface density is high, the surface energy is high, and the bonding is not easy. The polymer coating can meet the bonding requirement to a certain extent, but has obvious defects of uncontrollable coating area, poor edge section, uneven coating, accumulated material at the edge, large shrinkage stress and the like. The other is the use of an optical grade pressure sensitive adhesive. The pressure sensitive adhesive is extremely convenient to use, has initial adhesion, can be positioned, can realize adhesion only by applying tiny pressure, does not need to be solidified, and has extremely high adhesion efficiency. However, the pressure-sensitive adhesive has low modulus and strength, and is easy to slip and poor in solvent resistance after long-term use.
To solve the above problems, the prior art generally starts from two directions, on one hand, the coating problem is optimized by adjusting the viscosity of the polymer coating and the coating process, but the effect is not ideal; on the other hand, the problems of slip and the like are improved by improving the modulus of the optical-grade pressure-sensitive adhesive, and the product performance can be improved to a certain degree by increasing the content of the hard monomer, changing the crosslinking density and the like, but in this way, the adhesive capability of the pressure-sensitive adhesive shows a trend of decreasing, and the comprehensive effect is still unsatisfactory.
Therefore, there is a need in the art for improvements that provide a more reliable solution.
Disclosure of Invention
The invention aims to solve the technical problem of providing a UV tackifying optical adhesive film for glass bonding and a preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical scheme: the UV tackifying optical adhesive film for glass bonding is obtained by coating and curing the UV tackifying optical adhesive, and comprises the following raw material components in parts by weight:
preferably, the epoxy resin is one or more of epoxy resin NPEL-128, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bis (3, 4-epoxycyclohexylmethyl) adipic acid, triglycidyl isocyanate and 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate.
Preferably, the acrylic epoxy copolymer is obtained by polymerizing the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate and 15-25 parts of epoxy monomer;
the epoxy monomer is one or a mixture of more of glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether and methallyl glycidyl ether.
Preferably, the diluent is an epoxy diluent selected from one or more of butyl glycidyl ether, C12-14 glycidyl ether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, p-tert-butylphenyl glycidyl ether, neopentyl glycol diglycidyl ether and cage polysilsesquioxane epoxy resin.
Preferably, the photoinitiator is one or more of hexafluoroantimonate sulfonium salt, hexafluoroantimonate iodonium salt, hexafluorophosphate sulfonium salt, hexafluorophosphate iodonium salt and isopropylbenzene ferrocenium hexafluorophosphate.
Preferably, the auxiliary agent comprises one or more of an antifoaming agent, a wetting agent, an adhesion promoter, a dispersing agent, a leveling agent and a coupling agent.
Preferably, the epoxy resin is a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate and an epoxy resin NPEL-128;
the diluent is a mixture of 1, 4-butanediol diglycidyl ether and cage-type polysilsesquioxane epoxy resin;
the photoinitiator is a mixture of sulfur hexafluorophosphate and a photoinitiator 184;
the auxiliary agent is a mixture of a coupling agent A-187, a flatting agent BYK333 and an adhesion promoter BYK 4510.
The invention also provides a preparation method of the UV tackifying optical adhesive film for glass bonding, which comprises the following steps:
s1, preparing an acrylic acid epoxy copolymer;
s2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, epoxy resin, a diluent, a photoinitiator and an auxiliary agent to obtain UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, and bonding a second release film on the adhesive surface after drying to obtain the UV tackifying optical adhesive film for glass bonding.
Preferably, the step S1 specifically includes:
s1-1, the following monomers in parts by weight: adding 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate, 15-25 parts of epoxy monomer and 100-200 parts of epoxy monomer into a solvent, introducing nitrogen, stirring and heating to 60-70 ℃, and reacting for 15-60min at constant temperature;
s1-2, adding an initiator accounting for 0.2-0.8% of the total mass of the monomers, and reacting for 2-8h;
s1-3, heating to 72-80 ℃, adding an initiator accounting for 0.2-0.8% of the total mass of the monomers, and reacting for 2-8h;
s1-4, cooling to 25-35 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
Preferably, the preparation method of the UV tackifying optical adhesive film for glass bonding comprises the following steps:
s1, preparing an acrylic acid epoxy copolymer:
s1-1, the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate, 15-25 parts of epoxy monomer and 150 parts of epoxy monomer are added into a solvent, nitrogen is introduced, stirring is carried out, the temperature is raised to 65 ℃, and the constant temperature reaction is carried out for 30min;
wherein the solvent is a mixture of ethyl acetate and toluene, and ethyl acetate: the weight part ratio of toluene is 1:2-2:1;
s1-2, adding an initiator AIBN accounting for 0.3% of the total mass of the monomers, and reacting for 4 hours;
s1-3, heating to 76 ℃, adding an initiator AIBN accounting for 0.5% of the total mass of the monomer, and reacting for 4 hours;
s1-4, cooling to 30 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
S2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, the epoxy resin, the diluent, the photoinitiator and the auxiliary agent under the conditions of light shielding and humidity less than 50%, so as to obtain the UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, baking for 5-15min at 100-120 ℃, and then attaching a second release film on the adhesive surface to obtain the UV tackifying optical adhesive film for glass adhesion.
The beneficial effects of the invention are as follows:
the invention provides a UV tackifying optical adhesive film for glass adhesion and a preparation method thereof, wherein an epoxy acrylic copolymer adopted in the preparation raw material of the adhesive film contains an epoxy monomer capable of being cured by UV, and ether bond and hydroxyl generated by epoxy ring opening have excellent adhesive force on inorganic materials such as glass and the like, and the formation of a crosslinked network further ensures the adhesion and the reliability of use; the introduction of the UV curable epoxy monomer ensures the film forming property and provides the modulus and the adhesive property of the product after curing;
the invention adopts the high-activity hexafluorophosphoric acid cationic initiator as the photoinitiator, thereby ensuring the solidification and providing excellent compatibility;
the adhesive film has higher initial adhesion strength to a base material, and can ensure a positioning effect; after positioning, the adhesive film can be further crosslinked and hardened under certain UV irradiation, the bonding capability of the hardened adhesive film to the base material is greatly improved, and meanwhile, the modulus and the strength of the adhesive film are also greatly improved, so that the bonding effect is ensured, the long-term use resistance is improved, and the adhesive film can be well applied to bonding of planar electronic glass.
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The test methods used in the following examples are conventional methods unless otherwise specified. The material reagents and the like used in the following examples are commercially available unless otherwise specified. The following examples were conducted under conventional conditions or conditions recommended by the manufacturer, without specifying the specific conditions. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The invention provides a UV tackifying optical adhesive film for glass bonding, which is obtained by coating and curing the UV tackifying optical adhesive, wherein the UV tackifying optical adhesive comprises the following raw material components in parts by weight:
wherein, the acrylic acid epoxy copolymer is obtained by polymerizing the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate and 15-25 parts of epoxy monomer;
the epoxy monomer is a (meth) acrylate or vinyl compound having a cationic reactive functional group, and in a preferred embodiment, the epoxy monomer is one or more of glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, methallyl glycidyl ether, or a mixture of two or more thereof.
Wherein the epoxy resin may be an aromatic glycidyl ether, a cycloaliphatic glycidyl ester, a hydrogenated glycidyl ether, and mixtures thereof, and in preferred embodiments the epoxy resin is one or more of the epoxy resins NPEL-128, bisphenol a diglycidyl ether, bisphenol F diglycidyl ether, bis (3, 4-epoxycyclohexylmethyl) adipic acid, triglycidyl isocyanate, 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate.
Wherein the diluent is an epoxy diluent (saturated or unsaturated containing cyclic and chain epoxy compounds having at least one epoxy terminus); in preferred embodiments, the diluent is one or more of butyl glycidyl ether, C12-14 glycidyl ether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, p-tert-butylphenyl glycidyl ether, neopentyl glycol diglycidyl ether, cage polysilsesquioxane epoxy.
Wherein the photoinitiator may be a diazonium salt, ferric salt, iodonium salt, sulfonium salt, or the like type of photoinitiator, in a preferred embodiment; the photoinitiator is one or more of hexafluoroantimonate sulfonium salt, hexafluoroantimonate iodonium salt, hexafluorophosphate sulfonium salt, hexafluorophosphate iodonium salt and isopropylbenzene ferrocene hexafluorophosphate.
In a preferred embodiment, the auxiliary agent comprises one or more of an antifoaming agent, a wetting agent, an adhesion promoter, a dispersant, a leveling agent, a coupling agent; for example, one or more of BYK-088, BYK A530, BYK 980, BYK DISER 163,BYK 333,BYK 3550, BYK 4500, BYK4510, KH560, KH 570, coupling agent A187, and the like may be included.
In a preferred embodiment, the epoxy resin is a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate and the epoxy resin NPEL-128;
the diluent is a mixture of 1, 4-butanediol diglycidyl ether and cage-type polysilsesquioxane epoxy resin;
the photoinitiator is a mixture of hexafluorophosphate thioium salt and photoinitiator 184;
the auxiliary agent is a mixture of a coupling agent A-187, a leveling agent BYK333 and an adhesion promoter BYK 4510.
The invention also provides a preparation method of the above UV tackifying optical adhesive film for glass bonding, which comprises the following steps:
s1, preparing an acrylic acid epoxy copolymer:
s1-1, the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate, 15-25 parts of epoxy monomer and 150 parts of epoxy monomer are added into a solvent, nitrogen is introduced, stirring is carried out, the temperature is raised to 65 ℃, and the constant temperature reaction is carried out for 30min;
wherein the solvent is a mixture of ethyl acetate and toluene, and ethyl acetate: the weight part ratio of toluene is 1:2-2:1;
s1-2, adding an initiator AIBN (azobisisobutyronitrile) accounting for 0.3% of the total mass of the monomers, and reacting for 4 hours;
s1-3, heating to 76 ℃, adding an initiator AIBN accounting for 0.5% of the total mass of the monomer, and reacting for 4 hours;
s1-4, cooling to 30 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
S2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, the epoxy resin, the diluent, the photoinitiator and the auxiliary agent under the conditions of light shielding and humidity less than 50%, so as to obtain the UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, baking for 5-15min at 100-120 ℃, and then attaching a second release film on the adhesive surface to obtain the UV tackifying optical adhesive film for glass adhesion.
The foregoing is a general inventive concept and the following detailed examples and comparative examples are provided on the basis thereof to further illustrate the invention.
(1) In the UV tackifying optical adhesive films for glass bonding provided in the following examples and comparative examples, the raw materials for preparing the UV tackifying optical adhesive are all commercial products except that the epoxy acrylate copolymer is self-made, and the specific sources are as follows:
the epoxy resin is a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate (CELLOXIDE 2021P of DAICEL) and epoxy resin NPEL-128 (Nanya);
the diluent is a mixture of 1, 4-butanediol diglycidyl ether (Anhui Xinyu XY 622) and cage polysilsesquioxane epoxy resin (SY-EPSO 102L of Nisshinbo);
the photoinitiator was a mixture of a sulfur hexafluorophosphate salt (mig 202, heavy duty in everstate) and a photoinitiator 184 (IGM);
the auxiliary agent comprises a coupling agent A-187 (gamma-glycidyl ether propyl trimethoxy silane, michael), a leveling agent BYK333 (BYK) and an adhesion promoter BYK4510 (Liansandra).
(2) The following examples and comparative examples were prepared by the same method as the UV tackifying optical adhesive film for glass bonding, except that the formulation components of the acrylic epoxy copolymer and the formulation components of the UV tackifying optical adhesive were used, and the method comprises the steps of:
s1, preparing an acrylic acid epoxy copolymer:
s1-1, the following monomers are used: adding butyl acrylate, hydroxypropyl acrylate, isobornyl acrylate, epoxy monomer and epoxy monomer into a four-neck flask provided with a stirrer, a condenser and a nitrogen pipe, adding 150 parts by weight of solvent (mixture of ethyl acetate and toluene in a weight part ratio of 1:2-2:1), introducing nitrogen, stirring and heating to 65 ℃, and reacting at constant temperature for 30min;
s1-2, adding an initiator AIBN (azobisisobutyronitrile) accounting for 0.3% of the total mass of the monomers, and reacting for 4 hours;
s1-3, heating to 76 ℃, adding an initiator AIBN accounting for 0.5% of the total mass of the monomer, and reacting for 4 hours;
s1-4, cooling to 30 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
S2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, the epoxy resin, the diluent, the photoinitiator and the auxiliary agent under the conditions of light shielding and humidity less than 50%, so as to obtain the UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, baking for 10min at 110 ℃, and then attaching the second release film on the adhesive surface to obtain the UV tackifying optical adhesive film for glass adhesion.
In the following examples and comparative examples, the formulation components of the acrylic epoxy copolymer are shown in the following Table 1, and the formulation components of the UV tackifying optical adhesive are shown in the following Table 2, all in units of parts by weight.
TABLE 1
TABLE 2
The following performance tests were conducted after curing the UV tackifying optical adhesive films for glass bonding prepared in examples 1 to 6 and comparative examples 1 to 4, wherein comparative example 2 failed to form a good film and was not conducted; the curing conditions are as follows: ultraviolet irradiation is performed at the wavelength of the UV-LED 365, and the accumulated energy is not less than 5000mj.
The test method of the storage modulus and Tg comprises the following steps: the cured test pieces were tested using a dynamic mechanical analyzer under the following conditions:
test instrument: dynamic mechanical analyzer (DMA 1, mettler tolio); test piece size: 10 x 6 x 0.2mm; temperature range: -35-80 ℃; rate of temperature rise: 3 ℃/min; deformation mode: a stretch mode; test frequency: 1Hz.
The test specific items and results are shown in table 3 below, in table 3, +.indicated that film formation was possible, ∈indicated that film formation was not possible, and Δ indicated that film formation was not possible.
TABLE 3 Table 3
As can be seen from the test results in Table 3, the UV tackifying optical adhesive films prepared in examples 1-5 are excellent in all properties;
comparative example 1, in which hydroxypropyl acrylate was not added during the synthesis of the epoxy acrylic copolymer, had too low polarity and poor adhesive properties of the product;
comparative example 2, which had severe shrinkage during coating and failed to film coating, was too polar due to the addition of excess hydroxypropyl acrylate to the synthetic epoxy acrylic copolymer;
in the epoxy acrylic copolymer synthesized in comparative example 3, the toluene proportion in the mixed solvent is too high, and the UV front adhesion performance of the product is poor, mainly due to too low polymerization;
comparative example 4 the toluene content in the mixed solvent at the time of synthesizing the epoxy acrylic copolymer was too low, and although the UV-front adhesion property of the product was good, the adhesion property after UV was greatly lowered mainly due to the excessively high polymerization.
Although embodiments of the present invention have been disclosed above, it is not limited to the use of the description and embodiments, it is well suited to various fields of use for the invention, and further modifications may be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the particular details without departing from the general concepts defined in the claims and the equivalents thereof.
Claims (10)
1. The UV tackifying optical adhesive film for glass bonding is characterized by being obtained by coating and curing the UV tackifying optical adhesive, and comprises the following raw material components in parts by weight:
2. the UV tackifying optical adhesive film for glass bonding according to claim 1 wherein the epoxy resin is one or more of epoxy NPEL-128, bisphenol a diglycidyl ether, bisphenol F diglycidyl ether, bis (3, 4-epoxycyclohexylmethyl) adipic acid, triglycidyl isocyanate, 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate.
3. The UV tackifying optical adhesive film for glass bonding according to claim 1, wherein the acrylic epoxy copolymer is obtained by polymerizing the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate and 15-25 parts of epoxy monomer;
the epoxy monomer is one or a mixture of more of glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether and methallyl glycidyl ether.
4. The UV tackifying optical adhesive film for glass bonding according to claim 1, wherein the diluent is an epoxy diluent selected from one or more of butyl glycidyl ether, C12-14 glycidyl ether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, p-tert-butylphenyl glycidyl ether, neopentyl glycol diglycidyl ether, cage polysilsesquioxane epoxy resin.
5. The UV tackifying optical adhesive film for glass bonding according to claim 1 wherein the photoinitiator is one or more of sulfonium hexafluoroantimonate, iodonium hexafluoroantimonate, sulfonium hexafluorophosphate, iodonium hexafluorophosphate, and isopropylbenzene ferrocenium hexafluorophosphate.
6. The UV tackifying optical adhesive film for glass bonding according to claim 1, wherein the auxiliary agent comprises one or more of defoamer, wetting agent, adhesion promoter, dispersant, leveling agent, coupling agent.
7. The UV curable optical film for glass bonding according to claim 1, wherein the epoxy resin is a mixture of 3, 4-epoxycyclohexylmethyl 3, 4-epoxycyclohexylformate and an epoxy resin NPEL-128;
the diluent is a mixture of 1, 4-butanediol diglycidyl ether and cage-type polysilsesquioxane epoxy resin;
the photoinitiator is a mixture of sulfur hexafluorophosphate and a photoinitiator 184;
the auxiliary agent is a mixture of a coupling agent A-187, a flatting agent BYK333 and an adhesion promoter BYK 4510.
8. A method for preparing a UV tackifying optical adhesive film for glass bonding according to any one of claims 1 to 7, comprising the steps of:
s1, preparing an acrylic acid epoxy copolymer;
s2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, epoxy resin, a diluent, a photoinitiator and an auxiliary agent to obtain UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, and bonding a second release film on the adhesive surface after drying to obtain the UV tackifying optical adhesive film for glass bonding.
9. The method for preparing a UV tackifying optical adhesive film for glass bonding according to claim 8, wherein the step S1 is specifically:
s1-1, the following monomers in parts by weight: adding 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate, 15-25 parts of epoxy monomer and 100-200 parts of epoxy monomer into a solvent, introducing nitrogen, stirring and heating to 60-70 ℃, and reacting for 15-60min at constant temperature;
s1-2, adding an initiator accounting for 0.2-0.8% of the total mass of the monomers, and reacting for 2-8h;
s1-3, heating to 72-80 ℃, adding an initiator accounting for 0.2-0.8% of the total mass of the monomers, and reacting for 2-8h;
s1-4, cooling to 25-35 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
10. The method for preparing a UV tackifying optical adhesive film for glass bonding according to claim 9, comprising the steps of:
s1, preparing an acrylic acid epoxy copolymer:
s1-1, the following monomers in parts by weight: 20-40 parts of butyl acrylate, 10-20 parts of hydroxypropyl acrylate, 30-50 parts of isobornyl acrylate, 15-25 parts of epoxy monomer and 150 parts of epoxy monomer are added into a solvent, nitrogen is introduced, stirring is carried out, the temperature is raised to 65 ℃, and the constant temperature reaction is carried out for 30min;
wherein the solvent is a mixture of ethyl acetate and toluene, and ethyl acetate: the weight part ratio of toluene is 1:2-2:1;
s1-2, adding an initiator AIBN accounting for 0.3% of the total mass of the monomers, and reacting for 4 hours;
s1-3, heating to 76 ℃, adding an initiator AIBN accounting for 0.5% of the total mass of the monomer, and reacting for 4 hours;
s1-4, cooling to 30 ℃ after the reaction is finished, and obtaining the epoxy acrylic copolymer.
S2, preparing a UV tackifying optical adhesive: mixing the epoxy acrylic copolymer, the epoxy resin, the diluent, the photoinitiator and the auxiliary agent under the conditions of light shielding and humidity less than 50%, so as to obtain the UV tackifying optical adhesive;
and S3, uniformly coating the UV tackifying optical adhesive prepared in the step S2 on the first release film, baking for 5-15min at 100-120 ℃, and then attaching a second release film on the adhesive surface to obtain the UV tackifying optical adhesive film for glass adhesion.
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