CN117229750A - Ultraviolet light curing polyurethane acrylate adhesive for lenses and preparation method thereof - Google Patents
Ultraviolet light curing polyurethane acrylate adhesive for lenses and preparation method thereof Download PDFInfo
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- CN117229750A CN117229750A CN202311200923.7A CN202311200923A CN117229750A CN 117229750 A CN117229750 A CN 117229750A CN 202311200923 A CN202311200923 A CN 202311200923A CN 117229750 A CN117229750 A CN 117229750A
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- acrylate
- adhesive
- ultraviolet light
- mass
- polyurethane acrylate
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- 239000000853 adhesive Substances 0.000 title claims abstract description 71
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 71
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 49
- 239000004814 polyurethane Substances 0.000 title claims abstract description 43
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 acrylic ester Chemical class 0.000 claims abstract description 41
- 239000004417 polycarbonate Substances 0.000 claims abstract description 41
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002009 diols Chemical class 0.000 claims abstract description 22
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000000945 filler Substances 0.000 claims abstract description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 14
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 9
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 9
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 9
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 5
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 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 3
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- IXLWNFFMNULFEO-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)O.CO.CO.C1CCCCCCCCC1 Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.CO.CO.C1CCCCCCCCC1 IXLWNFFMNULFEO-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-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
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012974 tin catalyst Substances 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 4
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims 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
- HNVAGBIANFAIIL-UHFFFAOYSA-N 2-hydroxy-2-methylpropanal Chemical compound CC(C)(O)C=O HNVAGBIANFAIIL-UHFFFAOYSA-N 0.000 claims 1
- VSHMCEJCHYPYDU-UHFFFAOYSA-N 2-morpholin-4-ylpropanal Chemical compound O=CC(C)N1CCOCC1 VSHMCEJCHYPYDU-UHFFFAOYSA-N 0.000 claims 1
- 125000006188 2-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- RDHSUTIDSFVNJL-UHFFFAOYSA-N OC(=O)C=C.CCCCCCCCCCCC(O)=O Chemical compound OC(=O)C=C.CCCCCCCCCCCC(O)=O RDHSUTIDSFVNJL-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- DKKXSNXGIOPYGQ-UHFFFAOYSA-N diphenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C1=CC=CC=C1 DKKXSNXGIOPYGQ-UHFFFAOYSA-N 0.000 claims 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims 1
- OEDAJYOQELMMFC-UHFFFAOYSA-N octadecanoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCCCCCCCCCCCCCCC(O)=O OEDAJYOQELMMFC-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 abstract description 31
- 239000000758 substrate Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 5
- 238000003848 UV Light-Curing Methods 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004831 Hot glue Substances 0.000 description 3
- YMCOIFVFCYKISC-UHFFFAOYSA-N ethoxy-[2-(2,4,6-trimethylbenzoyl)phenyl]phosphinic acid Chemical compound CCOP(O)(=O)c1ccccc1C(=O)c1c(C)cc(C)cc1C YMCOIFVFCYKISC-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- MTEZSDOQASFMDI-UHFFFAOYSA-N 1-trimethoxysilylpropan-1-ol Chemical compound CCC(O)[Si](OC)(OC)OC MTEZSDOQASFMDI-UHFFFAOYSA-N 0.000 description 1
- NQGDHQASSFDDLD-UHFFFAOYSA-N 3-[2,2-dimethyl-3-(3-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(C)(C)COCCCOC(=O)C=C NQGDHQASSFDDLD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 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 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides an ultraviolet light curing polyurethane acrylate adhesive for lenses and a preparation method thereof, wherein the ultraviolet light curing polyurethane acrylate adhesive comprises polyurethane acrylate prepolymer, acrylic ester, silicon dioxide filler, an ultraviolet light catalyst and a silane coupling agent; the polyurethane acrylate prepolymer comprises aliphatic isocyanate and polycarbonate diol; therefore, the prepolymer which has the advantages of excellent temperature resistance and moisture resistance, low curing shrinkage and excellent bonding effect with the polycarbonate substrate is provided, and meanwhile, different acrylic esters, photoinitiators and fillers are matched to prepare the UV curing adhesive. The method solves the practical problems that the UV polyurethane acrylate for the lens is easy to lose efficacy in a high-temperature high-humidity state, the shrinkage rate in the curing process is high, the lens is deviated, and meanwhile, the adhesion with a PC base material is poor.
Description
Technical Field
The invention relates to a preparation method of an adhesive for lenses, in particular to an ultraviolet light curing polyurethane acrylate adhesive for lenses and a preparation method thereof.
Background
Currently, adhesives for lenses in the market are roughly classified into two types, namely hot melt adhesives and ultraviolet curing adhesives. The hot melt adhesive is slowly coming out of the market due to the fact that the hot melt adhesive needs to be cured under the high temperature condition and is easy to damage electronic components. The UV adhesive is widely applied in the field of lens bonding due to the advantages of rapid curing at normal temperature, convenient operation and the like.
In a plurality of UV ultraviolet curing adhesives, urethane bonds in urethane acrylate in the UV urethane acrylate adhesives can form a plurality of hydrogen bonds to enhance the mechanical property and chemical stability, and meanwhile, the ultraviolet curing adhesives have the weather resistance and better impact resistance of acrylate, but meanwhile, the urethane acrylate adhesives still have the defects of poor heat resistance and moisture resistance, high curing shrinkage and poor adhesion with PC base materials.
Therefore, the research on the UV type polyurethane acrylate adhesive with excellent heat resistance and moisture resistance, low curing shrinkage and good adhesion with the polycarbonate substrate has practical significance.
Disclosure of Invention
The invention aims to provide a prepolymer which has excellent heat resistance and moisture resistance, low curing shrinkage and excellent bonding effect with a polycarbonate substrate, and meanwhile, the prepolymer is matched with different acrylic esters, photoinitiators and fillers to prepare a UV curing adhesive.
In order to achieve the above purpose, the invention provides an ultraviolet light curing polyurethane acrylate adhesive for lenses, which comprises polyurethane acrylate prepolymer, acrylate, silica filler, ultraviolet light catalyst and silane coupling agent;
wherein the polyurethane acrylate prepolymer comprises aliphatic isocyanate and polycarbonate diol.
Further, the polycarbonate diol is a polycarbonate diol with a copolymerization C5/C6 molecular mass of 2000, a copolymerization C5/C6 molecular mass of 1000, a homopolymerization C6 molecular mass of 2000 or a homopolymerization C6 molecular mass of 1000.
Further, the aliphatic isocyanate is one or a combination of more than one of hexamethylene diisocyanate, isophorone diisocyanate and dicyclohexylmethane diisocyanate.
Further, the polyurethane acrylate prepolymer also comprises hydroxy acrylate, wherein the hydroxy acrylate is one or a mixture of more of hydroxy ethyl acrylate, pentaerythritol triacrylate, hydroxy propyl acrylate, hydroxy ethyl methacrylate and hydroxy propyl methacrylate;
the polyurethane acrylate prepolymer is monofunctional aliphatic polycarbonate polyurethane acrylate and accounts for 37% of the total mass of the adhesive.
Further, the acrylic ester is one or more of norbornene acrylic ester, hydroxyethyl (methyl) acrylate, hydroxypropyl (methyl) acrylate, 2-phenoxyethyl acrylate, lauric acid acrylic ester, stearic acid acrylic ester, isodecyl acrylic ester, propoxylated neopentyl glycol diacrylate and cyclodecane dimethanol diacrylate.
Further, the ultraviolet light catalyst is one or two of 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-4-methylthiophenyl) -2-morpholine-1-acetone, 2-hydroxy-2-methyl-1-4-2-hydroxyethoxy) phenyl-1-acetone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-hydroxy-4-2-methylbenzophenone, benzil dimethyl ether, 2,4, 6-trimethylbenzoyl diphenyl phosphorus oxide, 2-phenylbenzyl-2-dimethylamine-1-4-morpholinobenzophenone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide, benzophenone and 2-isopropylthioxanthone.
Further, the silane coupling agent is one or two of aminopropyl triethoxy silane, gamma-aminopropyl methyl diethoxy silane, gamma-aminopropyl triethoxy silane, gamma-aminopropyl trimethoxy silane or gamma-glycidol ether oxypropyl trimethoxy silane.
Further, the addition amount of the polyurethane acrylic ester prepolymer accounts for 30-45% of the mass fraction of the adhesive; the addition amount of the acrylic ester accounts for 30-45 wt% of the mass fraction of the adhesive; the addition amount of the silicon dioxide filler accounts for 15-30wt% of the mass fraction of the adhesive; the addition amount of the ultraviolet light catalyst accounts for 1-3 wt% of the mass fraction of the adhesive.
The invention also provides a preparation method of the ultraviolet light curing polyurethane acrylate adhesive for the lens, which comprises the following steps:
step 1: preparation of polyurethane acrylate prepolymer:
step 1.1: vacuum dewatering polycarbonate diol at 100-110 deg.c until no bubble is produced;
step 1.2: adding 1-3 parts by mass of aliphatic isocyanate into 5-10 parts by mass of polycarbonate diol, and reacting for 1-3 hours at a constant temperature of 30-60 ℃ under the protection of nitrogen atmosphere;
step 1.3: after the reaction is completed, adding 1 to 2 parts by mass of hydroxyl acrylate and 0.1 to 0.3 part by mass of tin catalyst, and carrying out constant temperature reaction for 1 to 4 hours at the temperature of between 30 and 60 ℃ under the protection of nitrogen atmosphere to obtain the polyurethane acrylate prepolymer.
Step 2: the ultraviolet light curing polyurethane acrylate adhesive is prepared by using 30-50 parts by mass of polyurethane acrylate prepolymer prepared in the step 1, 20-40 parts by mass of acrylate, 10-20 parts by mass of silica filler, 1-5 parts by mass of ultraviolet light catalyst and 1-3 parts by mass of silane coupling agent.
Compared with the prior art, the invention has the advantages that:
1. according to the invention, the polycarbonate diol is introduced into the prepolymer as the long-chain diol thereof, so that the heat resistance and moisture resistance of the adhesive are enhanced, the good bonding effect with the PC substrate is that the polycarbonate diol has high rigidity, so that the shrinkage stress transmission in the curing process is hindered, and the curing shrinkage rate is reduced. Meanwhile, aliphatic diisocyanate is selected to reduce the viscosity of the adhesive, so that the coating effect and the water resistance of the adhesive are enhanced, and meanwhile, as the two structures are long-chain carbon types and are similar in structure, the phase separation phenomenon of the adhesive is reduced. The prepared adhesive is introduced with acrylate with high rigidity to reduce curing shrinkage, the addition of silicon dioxide enhances mechanical property, enhances heat resistance and humidity resistance, delays easy flow of molecular chains in a system before a gel point reaches the gel point in the curing process, and can release shrinkage stress through plastic flow so as to eliminate the shrinkage stress before the curing film reaches the gel point and disperse the shrinkage stress. The introduction of the silane coupling agent enables the silicon dioxide to be better dispersed in the organic system, and meanwhile, the bonding strength of the silicon dioxide and glass is enhanced.
2. The polyurethane acrylate adhesive generally uses polyester polyurethane acrylate as a prepolymer, and polyester is easy to hydrolyze with water under the condition of acid and alkali, so that the bonding effect of the adhesive and a substrate is weakened. The polycarbonate in the polycarbonate polyurethane acrylic ester prepolymer has stable performance and is not easy to hydrolyze, and the polycarbonate polyurethane acrylic ester prepolymer can still keep stable performance under the high-temperature and high-humidity state.
3. The curing process of the UV adhesive is very rapid and can be completed within 20 seconds. In the gel process, the acting force between the acrylic ester monomer molecules, polyurethane acrylic ester prepolymer and other raw material molecules is changed into covalent bond connection, so that the distance between atoms is shortened from 0.3-0.5 nm to 0.154nm, and volume shrinkage is generated in the polymerization process.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be further described below.
Example 1:
100g of polycarbonate diol with the molecular weight of 1000 of the copolymer (C5/C6) is heated in a water bath at the temperature of 100 ℃, the water is distilled under reduced pressure, 66.4g of hexamethylene diisocyanate is added, the reaction is carried out for 1 hour at the temperature of 60 ℃ in the N2 atmosphere, and 49.6g of pentaerythritol triacrylate is added for continuous reaction for 2 hours. Making into prepolymer.
2wt% of 2,4, 6-trimethylbenzoyl diphenyl oxygen phosphorus, 1wt% of 1-hydroxy cyclohexyl phenyl ketone photoinitiator are dissolved in 7wt% of norbornene acrylic ester 10wt% of isodecyl acrylic ester 10wt% of propoxylated neopentyl glycol diacrylate at 80 ℃, 37wt% of prepolymer is dissolved in the solution at 60 ℃, 30wt% of silicon dioxide powder, 2wt% of aminopropyl triethoxysilane and 1wt% of gamma-aminopropyl trimethoxysilane are added, and the mixture is uniformly mixed to prepare the adhesive for the lens.
Example 2:
200g of a polycarbonate diol with a molecular mass of 2000 is firstly heated in a water bath at 100 ℃, the water is distilled under reduced pressure, 66.4g of hexamethylene diisocyanate is added, the reaction is carried out for 1 hour at 50 ℃ in N2 atmosphere, and 26.14g of hydroxyethyl methacrylate is added for further reaction for 2 hours. Making into prepolymer.
2wt% of 2,4, 6-trimethylbenzoyl diphenyl oxygen phosphorus, 1wt% of 2,4, 6-trimethylbenzoyl phenyl phosphonic acid ethyl ester photoinitiator is dissolved in 7wt% of norbornene acrylic ester, 10wt% of isodecyl acrylic ester and 8wt% of neopentyl glycol propoxylate diacrylate, 39wt% of prepolymer is dissolved in the solution at 60 ℃, 30wt% of silicon dioxide powder is added, and 1wt% of gamma-aminopropyl trimethoxysilane is uniformly mixed to prepare the adhesive for the lens.
Example 3:
100g of polycarbonate diol with the molecular weight of 1000 of homo-polymerized C6 is heated in a water bath at the temperature of 100 ℃, the water is distilled under reduced pressure, 33.6g of hexamethylene diisocyanate is added, the reaction is carried out for 1 hour at the temperature of 50 ℃ in a nitrogen atmosphere, and 26.14g of hydroxyethyl methacrylate is added for continuous reaction for 2 hours. Making into prepolymer.
2wt% of 2,4, 6-trimethylbenzoyl diphenyl oxygen phosphorus, 1wt% of 2,4, 6-trimethylbenzoyl phenyl phosphonic acid ethyl ester photoinitiator is dissolved in 7wt% of norbornene acrylic ester, 10wt% of isodecyl acrylic ester and 8wt% of ethyl methacrylate, 39wt% of prepolymer is dissolved in the solution at 60 ℃, 30wt% of calcium carbonate powder and 1wt% of gamma-aminopropyl trimethoxysilane are added, and the mixture is uniformly mixed to prepare the adhesive for the lens.
Example 4:
100g of polycarbonate diol T5651 is heated in a water bath at 100 ℃, the water content is distilled under reduced pressure, 33.6g of hexamethylene diisocyanate is added, the reaction is carried out for 1 hour under the nitrogen atmosphere at 50 ℃, and 26.14g of hydroxyethyl methacrylate is added for further reaction for 2 hours. Making into prepolymer.
2wt% of 2,4, 6-trimethylbenzoyl diphenyl oxygen phosphorus, 1wt% of 2,4, 6-trimethylbenzoyl phenyl phosphonic acid ethyl ester photoinitiator is dissolved in 7wt% of norbornene acrylic ester, 10wt% of stearic acid acrylic ester and 8wt% of methacrylic acid ethyl ester at 80 ℃, 39wt% of prepolymer is dissolved in the solution at 60 ℃, 30wt% of calcium carbonate powder and 1wt% of gamma-aminopropyl trimethoxysilane are added, and the mixture is uniformly mixed to prepare the adhesive for the lens. Example 5
100g of polycarbonate diol with the molecular weight of 1000 of the copolymer (C5/C6) is heated in a water bath at the temperature of 100 ℃, the water is distilled under reduced pressure, 44.4g of isophorone diisocyanate is added, the reaction is carried out for 1 hour at the temperature of 60 ℃ in the N2 atmosphere, 49.6g of pentaerythritol triacrylate is added, and the reaction is continued for 2 hours. Making into prepolymer.
2wt% of benzophenone, 1wt% of 1-hydroxycyclohexyl phenyl ketone photoinitiator are dissolved in 7wt% of norbornene acrylic ester, 10wt% of isodecyl acrylic ester and 10wt% of 2-phenoxyethyl acrylic ester at 80 ℃, 37wt% of prepolymer is dissolved in solution at 60 ℃, 30wt% of silicon dioxide powder, 2wt% of aminopropyl triethoxysilane and 1wt% of gamma-aminopropyl triethoxysilane are added, and the mixture is uniformly mixed to prepare the adhesive for the lens.
The adhesive for lenses is prepared by dissolving 2wt% of benzophenone, 1wt% of 1-hydroxycyclohexyl phenyl ketone photoinitiator in 7wt% of norbornene acrylic ester 10wt% of isodecyl acrylic ester 10wt% of 2-phenoxyethyl acrylic ester at 80 ℃, dissolving the pre-polymer resin of the CN9001S of the saromo company in the solution at 60 ℃, adding 30wt% of silicon dioxide powder, 2wt% of aminopropyl triethoxysilane and 1wt% of gamma-aminopropyl triethoxysilane into the solution, and uniformly mixing.
The detection method comprises the following steps:
adhesive strength: the tensile shear strength of PC to PC was tested according to GB/T7124-2008 standard, and curing conditions were 6000mJ/cm2.. The glass chip with the specification of 2mm multiplied by 2mm and full of the UV adhesive is adhered on a PC substrate board, and is fully irradiated for 20s in an ultraviolet irradiation box. Thrust testing was performed using a thrust meter.
Cure shrinkage: 1mL of adhesive was sampled by a syringe, the weight was 1, 0.5mL of adhesive was discharged, the weight was 2, and the operation was repeated three times to obtain the mass of the adhesive at 0.5mL, and the density before curing was obtained. And (3) taking about 1mL of the UV adhesive, putting the UV adhesive into an ultraviolet curing box to cure for 20 seconds, taking out the UV adhesive, and putting the UV adhesive into a density balance to measure the cured density.
Double 85 temperature and humidity resistance test: placing the cured bonding sample of the PC-PC substrate and the bonding sample of the glass chip-PC substrate into a high-temperature high-humidity oven, standing for 1000 hours at 85 ℃ under the condition of 85% relative humidity according to the GB/T5170-2016 standard, and testing the bonding strength and comparing the bonding strength with the bonding strength measured at the normal temperature.
Table 1 table of performance test data
Results and analysis:
as can be seen from the data in the table, compared with comparative example 1, the adhesive strength and the curing shrinkage rate of the invention of the example 1-5 are 1000h, and the invention has better adhesive strength, heat resistance and moisture resistance and lower curing shrinkage rate, and the addition of the star polyurethane acrylate prepolymer of the polycarbonate has the advantages of keeping the adhesive force to PC, improving the heat resistance and moisture resistance of the glue and reducing the shrinkage rate in the curing process.
Therefore, the self-made polyurethane acrylate prepolymer ester is added into the colloid, so that the adhesive has high cohesive force, high temperature resistance and moisture resistance, and low curing shrinkage rate, and the example 1 is optimal, and can be widely applied to the field of lens adhesion.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Conclusion: the scheme discloses a UV polyurethane acrylate adhesive, wherein a polycarbonate modified polyurethane acrylate prepolymer is introduced into the adhesive. Therefore, the bonding strength of the adhesive and the PC substrate is improved, the heat resistance and moisture resistance are improved, and the curing shrinkage rate is reduced. The adhesive prepared by the scheme has better bonding strength, heat resistance, moisture resistance and curing shrinkage than the adhesive prepared by the resin CN9001S resin commonly used in the market
The foregoing is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Any person skilled in the art will make any equivalent substitution or modification to the technical solution and technical content disclosed in the invention without departing from the scope of the technical solution of the invention, and the technical solution of the invention is not departing from the scope of the invention.
Claims (9)
1. The ultraviolet light curing polyurethane acrylate adhesive for the lenses is characterized by comprising polyurethane acrylate prepolymer, acrylate, silica filler, ultraviolet light catalyst and silane coupling agent;
wherein the polyurethane acrylate prepolymer comprises aliphatic isocyanate and polycarbonate diol.
2. The ultraviolet light curable urethane acrylate adhesive for lenses according to claim 1, wherein said polycarbonate diol is a polycarbonate diol having a copolymerized C5/C6 molecular mass of 2000, a polycarbonate diol having a copolymerized C5/C6 molecular mass of 1000, a polycarbonate diol having a homo-C6 molecular mass of 2000 or a polycarbonate diol having a homo-C6 molecular mass of 1000.
3. The uv curable urethane acrylate adhesive for lenses according to claim 1, wherein said aliphatic isocyanate is one or a combination of more of hexamethylene diisocyanate, isophorone diisocyanate and dicyclohexylmethane diisocyanate.
4. The uv curable urethane acrylate adhesive for lenses according to claim 1, wherein said urethane acrylate prepolymer further comprises hydroxy acrylate which is a mixture of one or more of hydroxy ethyl acrylate, pentaerythritol triacrylate, hydroxy propyl acrylate, hydroxy ethyl methacrylate and hydroxy propyl methacrylate;
the polyurethane acrylate prepolymer is monofunctional aliphatic polycarbonate polyurethane acrylate and accounts for 37% of the total mass of the adhesive.
5. The ultraviolet light curable urethane acrylate adhesive for lenses according to claim 1, wherein the acrylate is one or more of norbornene acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2-phenoxyethyl acrylate, lauric acid acrylate, stearic acid acrylate, isodecyl acrylate, propoxylated neopentyl glycol diacrylate and cyclodecane dimethanol diacrylate.
6. The ultraviolet light curable urethane acrylate adhesive for lenses according to claim 1, wherein said ultraviolet light catalyst is one or two of 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-4-methylthiophenyl butanone, 2-morpholino-1-propanone, 2-hydroxy-2-methyl-1-4-2-hydroxyethoxy) phenyl-1-propanone, 2-hydroxy-2-methyl-1-propanone, 2-hydroxy-4-2-hydroxyethoxy) -2-methylpropenyl propanone, benzildimethyl ether, 2,4, 6-trimethylbenzoyl diphenyl phosphorus, 2-phenylbenzyl 2-dimethylamine-1-4-morpholinobenzoyl) butanone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide, benzophenone and 2-isopropylthioxanthone.
7. The ultraviolet light curing polyurethane acrylate adhesive for lenses according to claim 1, wherein the silane coupling agent is one or two of amino functional silane such as aminopropyl triethoxysilane, gamma-aminopropyl methyldiethoxysilane, gamma-aminopropyl triethoxysilane, gamma-aminopropyl trimethoxysilane or gamma-glycidyloxypropyl trimethoxysilane.
8. The ultraviolet light curing polyurethane acrylate adhesive for lenses according to claim 1, wherein the addition amount of the polyurethane acrylate prepolymer is 30-45% by weight of the adhesive; the addition amount of the acrylic ester accounts for 30-45 wt% of the mass fraction of the adhesive; the addition amount of the silicon dioxide filler accounts for 15-30wt% of the mass fraction of the adhesive; the addition amount of the ultraviolet light catalyst accounts for 1-3 wt% of the mass fraction of the adhesive.
9. A method for preparing the ultraviolet light curing polyurethane acrylate adhesive for lenses, which is characterized by comprising the following steps of:
step 1: preparation of polyurethane acrylate prepolymer:
step 1.1: vacuum dewatering polycarbonate diol at 100-110 deg.c until no bubble is produced;
step 1.2: adding 1-3 parts by mass of aliphatic isocyanate into 5-10 parts by mass of polycarbonate diol, and reacting for 1-3 hours at a constant temperature of 30-60 ℃ under the protection of nitrogen atmosphere;
step 1.3: after the reaction is completed, adding 1 to 2 parts by mass of hydroxyl acrylate and 0.1 to 0.3 part by mass of tin catalyst, and carrying out constant temperature reaction for 1 to 4 hours at the temperature of between 30 and 60 ℃ under the protection of nitrogen atmosphere to obtain the polyurethane acrylate prepolymer.
Step 2: the ultraviolet light curing polyurethane acrylate adhesive is prepared by using 30-50 parts by mass of polyurethane acrylate prepolymer prepared in the step 1, 20-40 parts by mass of acrylate, 10-20 parts by mass of silica filler, 1-5 parts by mass of ultraviolet light catalyst and 1-3 parts by mass of silane coupling agent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111117553A (en) * | 2019-12-31 | 2020-05-08 | 东莞市德聚胶接技术有限公司 | UV (ultraviolet) photocuring and low-temperature thermosetting dual-curing adhesive and preparation method thereof |
| WO2022151949A1 (en) * | 2021-01-13 | 2022-07-21 | 浙江佑谦特种材料有限公司 | Aqueous polyurethane acrylate emulsion and application thereof |
| CN115386329A (en) * | 2022-10-11 | 2022-11-25 | 东莞市德聚胶接技术有限公司 | UV moisture dual-curing adhesive for electronic components |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111117553A (en) * | 2019-12-31 | 2020-05-08 | 东莞市德聚胶接技术有限公司 | UV (ultraviolet) photocuring and low-temperature thermosetting dual-curing adhesive and preparation method thereof |
| WO2022151949A1 (en) * | 2021-01-13 | 2022-07-21 | 浙江佑谦特种材料有限公司 | Aqueous polyurethane acrylate emulsion and application thereof |
| CN115386329A (en) * | 2022-10-11 | 2022-11-25 | 东莞市德聚胶接技术有限公司 | UV moisture dual-curing adhesive for electronic components |
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