CN105111998B - Ultraviolet light curing adhesive - Google Patents
Ultraviolet light curing adhesive Download PDFInfo
- Publication number
- CN105111998B CN105111998B CN201510599894.5A CN201510599894A CN105111998B CN 105111998 B CN105111998 B CN 105111998B CN 201510599894 A CN201510599894 A CN 201510599894A CN 105111998 B CN105111998 B CN 105111998B
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- parts
- acrylate
- adhesive
- urethane acrylate
- ultraviolet light
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 102
- 239000000853 adhesive Substances 0.000 title claims abstract description 100
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000003085 diluting agent Substances 0.000 claims abstract description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 28
- 229920000728 polyester Polymers 0.000 claims abstract description 24
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000006096 absorbing agent Substances 0.000 claims description 13
- -1 acrylic Ester Chemical class 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000004611 light stabiliser Substances 0.000 claims description 9
- 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 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical class CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 claims description 3
- FVWQVDPNRUAXBQ-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)O.C(C)(C)(C)C=1C(=C(C=C(C1)C(C)(C)C)CCC(=O)O)O Chemical compound C(CCCCCCCCCCCCCCCCC)O.C(C)(C)(C)C=1C(=C(C=C(C1)C(C)(C)C)CCC(=O)O)O FVWQVDPNRUAXBQ-UHFFFAOYSA-N 0.000 claims description 3
- BDMNXZALGYQDBL-UHFFFAOYSA-N CC1=C(C(=O)O)C=CC=C1C(=O)O.C(CCCCCCCCC(=O)O)(=O)O Chemical group CC1=C(C(=O)O)C=CC=C1C(=O)O.C(CCCCCCCCC(=O)O)(=O)O BDMNXZALGYQDBL-UHFFFAOYSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 3
- MZRQZJOUYWKDNH-UHFFFAOYSA-N diphenylphosphoryl-(2,3,4-trimethylphenyl)methanone Chemical class CC1=C(C)C(C)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MZRQZJOUYWKDNH-UHFFFAOYSA-N 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 229940116351 sebacate Drugs 0.000 claims description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 3
- DYULYMCXVSRUPB-UHFFFAOYSA-N 1,4-bis(phenylmethoxy)benzene Chemical group C=1C=CC=CC=1COC(C=C1)=CC=C1OCC1=CC=CC=C1 DYULYMCXVSRUPB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- DTTDXHDYTWQDCS-UHFFFAOYSA-N 1-phenylcyclohexan-1-ol Chemical group C=1C=CC=CC=1C1(O)CCCCC1 DTTDXHDYTWQDCS-UHFFFAOYSA-N 0.000 claims 1
- ZCJLOOJRNPHKAV-UHFFFAOYSA-N 3-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CO1 ZCJLOOJRNPHKAV-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 4
- 238000001723 curing Methods 0.000 description 50
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 238000004383 yellowing Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000006750 UV protection Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical class C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- UXMQORVHJMUQFD-UHFFFAOYSA-N Heptanophenone Chemical compound CCCCCCC(=O)C1=CC=CC=C1 UXMQORVHJMUQFD-UHFFFAOYSA-N 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 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
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a kind of ultraviolet light curing adhesive.The ultraviolet light curing adhesive, in parts by weight, including 5~20 parts of polyester acrylate oligomers, 15~35 parts of urethane acrylate, 5~20 parts of epoxy acrylate, 50~120 parts of reactive diluent and 1~3 part of light trigger.Simultaneously comprising three kinds of polyester acrylate oligomers, urethane acrylate and epoxy acrylate unsaturated oligomers in above-mentioned adhesive, this can be effectively improved the adhesion strength and weatherability of adhesive, adhesive is had preferable combination property.The dosage of each component is limited simultaneously and is advantageous to obtain the ultraviolet light curing adhesive for having high bonding strength, good weatherability properties and good coating waste water performance concurrently within the above range.
Description
Technical field
The present invention relates to Photocurable adhesive field, in particular to a kind of ultraviolet light curing adhesive.
Background technology
Ultraviolet light curing adhesive be it is a kind of have solidify rapid, green, bonding force is strong, solidification when without fuel factor and
The adhesive of the features such as wide adaptation range.Its principle is using light trigger under ultraviolet light, triggers unsaturated organic list
Body the chemical reaction such as is polymerize, is grafted, is crosslinked and reaching a kind of adhesive solidified rapidly.Due to hardening time is short, energy
The features such as utilization rate is high, solidification temperature is low, free from environmental pollution is measured, so it receives the extensive concern of people once appearance.
Publication No. CN102898980 patent application provides a kind of ultraviolet curing acrylic ester adhesive, its by
Methyl methacrylate, butyl acrylate, vinylacetate and toluene etc. are made.The adhesive has curing rate fast, viscous
The advantages that intensity is high and shock resistance is good is connect, is widely used to the bonding of the multiple materials such as metal, glass, crystal and stone material,
With preferable economic results in society.But for the adhesive there is also many weak points, such as using toluene as solvent, there is ring in it
The problems such as high, impact resistance difference and light are polluted in border, heat endurance is relatively low.
Grant number provides a kind of Liquid optical clear adhesive for liquid crystal display touch screen for CN102732183 Chinese patent, its
It is made by liquid synthetic rubber, terpene resin, latent curing agent, light trigger with antioxidant etc..The transparent adhesive tape has printing opacity
The advantages that property is good, ductility is good and yellowing resistance is excellent.But there is also to the inorganic ground such as a variety of organic substrates and glass
The problem of adhesive strength deficiency.
Grant number provides a kind of ultraviolet light curing adhesive for CN101701143 Chinese patent, its by polyester-type and
Urethane diacrylate oligomer, isobornyl acrylate isoreactivity free radical monomer, 1- hydroxycyclohexyl phenylketones and silicon
Alkane coupling agent etc. is made.The adhesive is applied to a variety of organic substrates, glass and metal etc., and moderate strength bonding can be achieved.
But the weatherability of material is not referred to, it is not suitable for outdoor application.
In a word, there is the defects of adhesion strength and weatherability can not get both in existing ultraviolet light curing adhesive.On in view of
State the presence of problem, it is necessary to prepare and a kind of have high bond strength and the ultraviolet curing adhesive of good weatherability properties concurrently.
The content of the invention
It is a primary object of the present invention to provide a kind of ultraviolet light curing adhesive, to solve UV-curing in the prior art
Change the problem of adhesive high bond strength and good weatherability properties can not get both.
To achieve these goals, one aspect of the invention provides a kind of ultraviolet light curing adhesive, in parts by weight,
The adhesive includes 5~20 parts of polyester acrylate oligomers, 15~35 parts of urethane acrylate, 5~20 parts of ring
Oxypropylene acid esters, 50~120 parts of reactive diluent and 1~3 part of light trigger.
Further, in parts by weight, adhesive include 8~12 parts polyester acrylate oligomers, 20~30 parts
Urethane acrylate, 8~15 parts of epoxy acrylate, 50~70 parts of reactive diluent and 1.5~3 parts it is light-initiated
Agent.
Further, the weight of reactive diluent and polyester acrylate oligomers, urethane acrylate and epoxy third
The ratio of three kinds of acrylate gross weights of olefin(e) acid ester is 4:6~6:4.
Further, reactive diluent is monofunctional compound；Polyester acrylate oligomers include 1~2 function
Base；Urethane acrylate includes 1~3 functional group；And epoxy acrylate includes 1~3 functional group.
Further, reactive diluent includes isobornyl acrylate, ethoxyethoxyethyl acrylate, tetrahydrochysene furan
Mutter acrylate and 4- hy-droxybutyls.
Further, in parts by weight, reactive diluent includes 5~20 parts of isobornyl acrylate, 5~25 parts of second
Epoxide ethoxyethyl acrylate, 20~40 parts of tetrahydrofuran acrylate and 20~30 parts of 4- acrylic acid hydroxyl fourths
Ester.
Further, urethane acrylate is aliphatic urethane acrylate, preferably single functionality aliphatic poly
Urethane acrylate and/or bifunctionality aliphatic urethane acrylate.
Further, in parts by weight, adhesive is also steady including 0.1~5 part of UV absorbers, 0.1~5 part of light
Determine agent and 0.2~1 part of antioxidant.
Further, in parts by weight, adhesive is also steady including 0.2~1 part of UV absorbers, 0.5~2 part of light
Determine agent and 0.5~1 part of antioxidant.
Further, light trigger is selected from 1- hydroxycyclohexyl phenyl ketones, 2,4,6 (trimethylbenzoyl) diphenyl
Phosphine oxide, 2- hydroxy-2-methyl -1- phenyl -1- acetone and 1,1- (- 4,1- the phenylenes of methylene-two) double [2- hydroxyl -2- first
Base -1- propane ketone] composition group in one or more；
UV absorbers are selected from hydroxyl phenol and triazine, the tert-amyl phenols of 2- (2H- BTA -2- bases) -4,6- two
With 6- methylheptyls 2- { 4- [4,6- bis- (4- xenyls) -1,3,5- triazine -2- bases] -3- hydroxyphenoxies } propionic ester composition
One or more in group；
Light stabilizer is selected from decanedioic acid methyl isophthalic acid, 2,2,6,6- pentamethyl -4- piperidine esters, two [2,2,6,6- tetramethyls -1-
(octyl group epoxide) -4- piperidyls] sebacate and it is poly- [6- [(1,1,3,3- tetramethyl butyls) amino]] -1,3,5- triazine -2,
4- [(2,2,6,6,-tetramethyl-4-piperidyl) imino group] -1,6- oneself two support [(2,2,6,6- tetramethyl -4- piperidyls) imido
Base] } composition group in one or more；
Antioxidant is selected from hydroquinone dibenzyl ether, β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid octadecanol fat
With the one or more in the group of four [β-(3,5- di-tert-butyl-hydroxy phenyls) propionic acid] pentaerythritol esters composition.
The invention provides a kind of ultraviolet light curing adhesive.Apply the technical scheme of the present invention, it is provided by the invention on
State in adhesive while include polyester acrylate oligomers, three kinds of unsaturations of urethane acrylate and epoxy acrylate
Oligomer.The viscosity of polyester acrylate oligomers is low, and preferable with the compatibility of other components so that adhesive has relatively low
Viscosity.Epocryl hydroxyl, ether, ester group isopolarity group, this design feature enable epoxy resin
Enough and adherend produces powerful interaction force, and it has higher photocuring activity, and this is advantageous to improve UV-curing
Change the bonding strength and polymerization of adhesive；Urethane acrylate has preferable pliability, especially low-temperature flexibility,
And its own also has good wearability, ageing resistance and high-tear strength, thus the addition of urethane acrylate is favourable
In combination properties such as the toughness, wearability, ageing resistance for improving ultraviolet curing adhesive.Above-mentioned three kinds of unsaturated oligomers are simultaneously
Use, the adhesion strength and weatherability of adhesive can be effectively improved, make adhesive that there is preferable combination property.In addition, will
The dosage of each component limits within the above range, be advantageous to obtain have concurrently high bonding strength, good weatherability properties and good coating plus
The ultraviolet light curing adhesive of work performance.
Embodiment
It should be noted that in the case where not conflicting, the feature in embodiment and embodiment in the application can phase
Mutually combination.The present invention is described in detail with reference to embodiment.
As described by background technology, the existing adhesion strength that binding agent be present is asked with what weatherability can not get both
Topic.In order to solve this problem, the invention provides a kind of ultraviolet light curing adhesive, and in parts by weight, the adhesive includes 5
~20 parts of polyester acrylate oligomers, 15~35 parts of urethane acrylate, 5~20 parts of epoxy acrylate, 50
~120 parts of reactive diluent and 1~3 part of light trigger.
In above-mentioned adhesive provided by the invention simultaneously include polyester acrylate oligomers, urethane acrylate and
Three kinds of unsaturated oligomers of epoxy acrylate.The viscosity of polyester acrylate oligomers is low, and with the compatibility of other components
Preferably so that adhesive has relatively low viscosity.Epocryl hydroxyl, ether, ester group isopolarity group, this
Design feature enables epoxy resin to produce powerful interaction force with adherend, and there is higher photocuring to live for it
Property, this is advantageous to the bonding strength and polymerization that improve ultraviolet light curing adhesive；Urethane acrylate has preferable
Pliability, especially low-temperature flexibility, and its own also has good wearability, ageing resistance and high-tear strength, thus
Being added with for urethane acrylate is beneficial to improve the combination properties such as the toughness, wearability, ageing resistance of ultraviolet curing adhesive.
Above-mentioned three kinds of unsaturated oligomers use simultaneously, can be effectively improved the adhesion strength and weatherability of adhesive, have adhesive
There is preferable combination property.In addition, the dosage of each component is limited within the above range, be advantageous to obtain that to have high bonding concurrently strong
The ultraviolet light curing adhesive of degree, good weatherability properties and good coating waste water performance.
Ultraviolet light curing adhesive is as long as there is said components, you can has higher bonding strength and well weather-proof concurrently
Property.In a preferred embodiment, in parts by weight, the adhesive include 8~12 parts polyester acrylate oligomers,
20~30 parts of urethane acrylate, 8~15 parts of epoxy acrylate, 50~70 parts of reactive diluent and 1.5~3
The light trigger of part.By the control of the ratios of said components within the above range, be advantageous to further to balance bonding strength, weather-proof
The performance of each side such as property, wearability, to obtain the more excellent ultraviolet light curing adhesive of performance.
In a preferred embodiment, the adhesive include polyester acrylate oligomers, urethane acrylate,
Epoxy acrylate, reactive diluent and light trigger；Wherein the weight of reactive diluent and polyester acrylate oligomers,
The ratio of three kinds of acrylate gross weights of urethane acrylate and epoxy acrylate is 4:6~6:4.By reactive diluent with gathering
The weight ratio of three kinds of acrylate sums of ester acrylate oligomer, urethane acrylate and epoxy acrylate is limited to
Be advantageous to further improve bonding strength, good weatherability properties and the good coating waste water of ultraviolet light curing adhesive in above range
Performance etc. combination property.
In a preferred embodiment, reactive diluent is monofunctional compound；Polyester acrylate oligomers
Include 1~2 functional group；Urethane acrylate includes 1~3 functional group；And epoxy acrylate includes 1~3 official
Can base.The functional group contained of above-mentioned each component is controlled within the above range respectively, is advantageous to that ultra-violet curing bonding will be prepared
The polymerization speed of agent is controlled in the range of more suitably.Matched somebody with somebody simultaneously by appropriate functional group and compare ultraviolet light curing adhesive most
Selection is adjusted in the network structure of whole solidification polymer, and it is comprehensive to make it have more preferable bonding strength, toughness, weatherability etc.
Performance.
It is public that the epoxy acrylate of single functionality includes the 620-100 of Changxing company, 6209 and RAHN of Changxing company
The 4188 of department；The epoxy acrylate of bifunctionality includes CN104NS and the MIWON public affairs of the 6210G of Changxing company, Sartomer
The MIRAMER230 of department；MIRAMER ERP400 of the epoxy acrylate of three-functionality-degree including MIWON companies, Changxing company
The GU1700P of 6261 and Guo Jing chemical companies.
The CN3108NS models of single functionality polyester acrylate oligomers including Sartomer, Changxing company
6314C-55 models and the D100 of ALLEX companies；The polyester acrylate oligomers of bifunctionality include Guo Jing chemical companies
The PS420 of GU8703D, MIWON company and the CN704 of Sartomer.
In above-mentioned ultraviolet light curing adhesive, reactive diluent can select reactive diluent commonly used in the art, as long as
The viscosity of adhesive can be adjusted for it.In a preferred embodiment, above-mentioned reactive diluent include but
It is not limited to isobornyl acrylate, ethoxyethoxyethyl acrylate, tetrahydrofuran acrylate and 4- acrylic acid hydroxyls
One or more in the group of butyl ester composition.Above-mentioned several reactive diluents are except that can reduce the viscous of ultraviolet light curing adhesive
It is outside one's consideration, there is good compatibility also between other several unsaturated oligomers, can further improves the synthesis of adhesive
Performance.Meanwhile itself as photo-curing monomer, also also have preferably tough with good photocuring activity, cured product
Property, it can further improve the toughness of adhesive.
According to the above-mentioned teaching of the present invention, those skilled in the art can select its different activities of specific reactive diluent
Proportionate relationship between diluent.In a preferred embodiment, in parts by weight, reactive diluent includes 5~20 parts
Isobornyl acrylate, 5~25 parts of ethoxyethoxyethyl acrylate, 20~40 parts of tetrahydrofuran acrylate
And 20~30 parts of 4- hy-droxybutyls.The proportionate relationship of each component in above-mentioned reactive diluent is controlled in above range
It is interior, be advantageous to further improve reactive diluent in the comprehensive of viscosity, penetration and the toughness of regulation adhesive etc.
Energy.
In above-mentioned ultraviolet light curing adhesive, those skilled in the art can select the type of urethane acrylate.
In a kind of preferred embodiment, urethane acrylate includes but is not limited to aliphatic urethane acrylate.Aliphatic poly
Urethane acrylate has good anti-yellowing property, adds the color inhibition that the component is advantageous to improve ultraviolet light curing adhesive
Performance.Preferably, it is single functionality aliphatic urethane acrylate and/or bifunctionality aliphatic urethane acrylate.
The aliphatic urethane acrylate of above-mentioned degree of functionality is selected, is advantageous to improve the anti-yellowing property of ultraviolet light curing adhesive,
Ensure that it has good reactivity simultaneously.Specifically, single functionality aliphatic urethane acrylate includes but is not limited to
Double bond chemical industry 5404 and/or RAHN 4188, bifunctionality aliphatic urethane acrylate include but is not limited to state and refined
GU3030Z and/or ALLEX EB8413.During practical application, two kinds in above-mentioned aliphatic urethane acrylate can be selected
Or two or more uses.
In above-mentioned ultraviolet light curing adhesive, those skilled in the art can select to add the type of auxiliary agent.A kind of excellent
In the embodiment of choosing, in parts by weight, adhesive is also stable including 0.1~5 part of UV absorbers, 0.1~5 part of light
Agent and 0.2~1 part of antioxidant.The UV absorbers, light stabilizer and antioxidant for adding aforementioned proportion are favourable
In the uv-resistance, heat-resisting xanthochromia and the fast light xanthochromia that improve ultraviolet light curing adhesive.
In a preferred embodiment, in parts by weight, described adhesive is also inhaled including 0.2~1 part of ultraviolet light
Receive agent, 0.5~2 part of light stabilizer and 0.5~1 part of antioxidant.UV absorbers, the light for adding aforementioned proportion are steady
Determine agent and antioxidant is advantageous to further improve uv-resistance, heat-resisting xanthochromia and the fast light xanthochromia of ultraviolet light curing adhesive
Property.
In above-mentioned ultraviolet light curing adhesive, those skilled in the art can select light trigger, UV absorbers, light
The type of stabilizer and antioxidant.In a preferred embodiment, light trigger includes but is not limited to 1- hydroxyl rings
Hexyl phenyl ketone, 2,4,6 (trimethylbenzoyl) diphenyl phosphine oxides, 2- hydroxy-2-methyl -1- phenyl -1- acetone and
One or more in the group of the 1,1- (- 4,1- phenylenes of methylene-two) double [2- hydroxy-2-methyl -1- propane ketone] compositions；It is purple
Outer light absorber include but is not limited to hydroxyl phenol and triazine, the tert-amyl phenols of 2- (2H- BTA -2- bases) -4,6- two and
The group of 6- methylheptyls 2- { 4- [4,6- bis- (4- xenyls) -1,3,5- triazine -2- bases] -3- hydroxyphenoxies } propionic ester composition
In one or more；Light stabilizer includes but is not limited to decanedioic acid methyl isophthalic acid, 2,2,6,6- pentamethyl -4- piperidine esters, two [2,
2,6,6- tetramethyls -1- (octyl group epoxide) -4- piperidyls] sebacate and poly- { [6- [(1,1,3,3- tetramethyl butyls) ammonia
Base]] -1,3,5- triazines -2,4- [(2,2,6,6,-tetramethyl-4-piperidyl) imino group] -1,6- oneself two support [(2,2,6,6- tetramethyls
Base -4- piperidyls) imino group] composition group in one or more；Antioxidant includes but is not limited to hydroquinones dibenzyl
Ether, β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid octadecanol fat and four [β-(3,5- di-tert-butyl-hydroxy phenyls)
Propionic acid] pentaerythritol ester composition group in one or more.Above-mentioned substance is selected to be advantageous to solidification is anti-as light trigger
The reaction rate answered is controlled in suitable scope；Above-mentioned substance is selected as UV absorbers, light stabilizer and antioxygen
Agent, it is comprehensive to be advantageous to further uv-resistance energy, heat-resisting xanthochromia and fast light xanthochromia of raising ultraviolet light curing adhesive etc.
Performance is closed, so as to improve its weatherability.
The present invention is further illustrated with reference to embodiment.
The raw material and manufacturer used in embodiment 1 to 14 and comparative example 1 is shown in Table 1.
Table 1
The preparation technology of ultraviolet curing adhesive is as follows in the embodiment of the present invention 1 to 14 and comparative example 1：
At normal temperatures and pressures, by reactive diluent, polyester acrylate oligomers, urethane acrylate, propylene oxide
Acid esters is mixed to get the first question response thing；Question response thing and light trigger are mixed to get the second question response thing, second treated anti-
Answer thing to be heated to 50 DEG C, stir simultaneously, transparency liquid is completely dissolved into light trigger；It is optional by being added in the second question response thing
UV absorbers, optional light stabilizer, optional antioxidant, stir 0.5h, static 2h, sampling Detection is qualified, mistake
Required ultraviolet light curing adhesive is made in filter.In manufacturing process, moistureproof lucifuge should be noted.
The component of obtained ultraviolet light curing adhesive is shown in Table 2 and table 3 respectively in embodiment 1 to 14 and comparative example 1.
Table 2
Table 3
The property of obtained ultraviolet light curing adhesive is shown in Table 4 and table 5 respectively in embodiment 1 to 14 and comparative example 1.
Viscosity：By BROOKFIELD DV2T type viscosimeters, at 25 DEG C, the viscosity of above-mentioned ultra-violet curing agent is carried out
Test.
Light transmittance：By HUNTER LAB COLORQUESTXE type sub-ray spectrometers, using projective techniques, to above-mentioned purple
The light transmittance of coated sand intensifier is tested.
Refractive index：By ATAGO NAR-1T type Abbe refractometers, the refractive index of above-mentioned ultra-violet curing agent is tested.
Colourity APHA：By MN VISOCOLOR type visual colorimetric determination instrument, the colourity APHA of above-mentioned ultra-violet curing agent is carried out
Test.
Water content：By PRECISA XM60 type karl Fischer moisture meters, the water content of above-mentioned ultra-violet curing agent is carried out
Test.
Outward appearance：Observe by the naked eye.
Table 4
Table 5
By the following method to the adhesive property of obtained ultraviolet light curing adhesive in embodiment 1 to 14 and comparative example 1
Tested：
Obtained adhesive in embodiment 1 to 14 and comparative example 1 is fitted on plastic basis material, coating 24um thickness glues
Mixture, the test film is reciprocally attached to the polyethylene terephthalate as clung body respectively using 2kg roller × 2 time
(PET), polyvinyl chloride (PVC), makrolon (PC), polystyrene (PS), polymethyl methacrylate (PMMA), on glass.
It is cut into that 25mm is wide, using the material of gained as test film, 180 is determined under 23 DEG C, 50%RH atmosphere after attaching 1 hour
Spend peel strength.Test result is shown in Table 6 and table 7 respectively.
Table 6
Table 7
The weatherability of obtained ultraviolet light curing adhesive in embodiment 1 to 14 and comparative example 1 is entered by the following method
Row test：
The assay method of initial yellowing degree (b*)：Using ColorQUEST XE type visible spectrometers, according to JIS
K7105 determines the initial yellowing degree (b*) of ultraviolet light curing adhesive.
Fast light xanthochromia degree (b* (UV)) assay method：Ultraviolet light curing adhesive is passed through into ultraviolet light in QUV testers
After irradiating 250h and 500h, using ColorQUEST XE type visible spectrometers, initial stage is determined according to JIS K7105
Xanthochromia degree (b* (UV)).
Heat-resisting xanthochromia degree (b* (heat) assay method：Obtained ultraviolet light curing adhesive is under 85 DEG C × 85%RH atmosphere
Place 250 hours and 500 hours, using ColorQUEST XE type visible spectrometers, determined according to JIS K7105
Initial yellowing degree (b* (heat).
Water boiling resistance assay method：By the boiling under the conditions of boiling water (100 DEG C) of obtained ultraviolet light curing adhesive, pass through
Different time tests bonding force situation.
The method of testing of bonding force is as described above.Test result is shown in Table 8 and table 9.
Table 8
Table 9
As can be seen from the above description, adhesive provided by the invention has preferable bonding strength, while also has
There is preferable weather resisteant.
In above-mentioned adhesive provided by the invention simultaneously include polyester acrylate oligomers, urethane acrylate and
Three kinds of unsaturated oligomers of epoxy acrylate.The viscosity of polyester acrylate oligomers is low, and with the compatibility of other components
Preferably so that adhesive has relatively low viscosity.Epocryl hydroxyl, ether, ester group isopolarity group, this
Design feature enables epoxy resin to produce powerful interaction force with adherend, and there is higher photocuring to live for it
Property, this is advantageous to the bonding strength and polymerization that improve ultraviolet light curing adhesive；Urethane acrylate has preferable
Pliability, especially low-temperature flexibility, and its own also has good wearability, ageing resistance and high-tear strength, thus
Being added with for urethane acrylate is beneficial to improve the combination properties such as the toughness, wearability, ageing resistance of ultraviolet curing adhesive.
Above-mentioned three kinds of unsaturated oligomers use simultaneously, can be effectively improved the adhesion strength and weatherability of adhesive, have adhesive
There is preferable combination property.In addition, the dosage of each component is limited within the above range, be advantageous to obtain that to have high bonding concurrently strong
The ultraviolet light curing adhesive of degree, good weatherability properties and good coating waste water performance.
The preferred embodiments of the present invention are the foregoing is only, are not intended to limit the invention, for the skill of this area
For art personnel, the present invention can have various modifications and variations.Within the spirit and principles of the invention, that is made any repaiies
Change, equivalent substitution, improvement etc., should be included in the scope of the protection.
Claims (10)
1. a kind of ultraviolet light curing adhesive, it is characterised in that in parts by weight, described adhesive includes 5~20 parts of polyester
Acrylate oligomer, 15~35 parts of urethane acrylate, 5~20 parts of epoxy acrylate, 50~120 parts of activity
Diluent and 1~3 part of light trigger；The reactive diluent is monofunctional compound；The polyester acrylate is low
Polymers includes 1~2 functional group；The urethane acrylate includes 1~3 functional group；And the epoxy acrylate
Include 1~3 functional group.
2. adhesive according to claim 1, it is characterised in that in parts by weight, described adhesive, including 8~12 parts
The polyester acrylate oligomers, 20~30 parts of the urethane acrylate, 8~15 parts of the epoxy acrylic
Ester, 50~70 parts of the reactive diluent and 1.5~3 parts of the light trigger.
3. adhesive according to claim 2, it is characterised in that the weight of the reactive diluent and the polyester
Acid esters oligomer, the ratio of three kinds of acrylate gross weights of the urethane acrylate and the epoxy acrylate are 4:6~
6:4。
4. adhesive according to claim 1, it is characterised in that the reactive diluent include isobornyl acrylate,
Ethoxyethoxyethyl acrylate, tetrahydrofuran acrylate and 4- hy-droxybutyls.
5. adhesive according to claim 4, it is characterised in that in parts by weight, the reactive diluent includes 5~20
Part the isobornyl acrylate, 5~25 parts of the ethoxyethoxyethyl acrylate, described the four of 20~40 parts
Hydrogen furanacrylate and 20~30 parts of the 4- hy-droxybutyls.
6. adhesive according to claim 1, it is characterised in that the urethane acrylate is aliphatic polyurethane third
Olefin(e) acid ester.
7. adhesive according to claim 6, it is characterised in that the aliphatic urethane acrylate is single functionality
Aliphatic urethane acrylate and/or bifunctionality aliphatic urethane acrylate.
8. the adhesive according to any one of claim 2 to 5, it is characterised in that in parts by weight, described adhesive is also
UV absorbers including 0.1~5 part, 0.1~5 part of light stabilizer and 0.2~1 part of antioxidant.
9. according to the adhesive described in claim 8, it is characterised in that in parts by weight, described adhesive also include 0.2~
1 part of the UV absorbers, 0.5~2 part of the light stabilizer and 0.5~1 part of the antioxidant.
10. according to the adhesive described in claim 8, it is characterised in that the light trigger is selected from 1- hydroxy-cyclohexyl benzene
Base ketone, 2,4,6 (trimethylbenzoyl) diphenyl phosphine oxides, 2- hydroxy-2-methyl -1- phenyl -1- acetone and 1,1- are (sub-
- 4,1- the phenylenes of methyl-two) double [2- hydroxy-2-methyl -1- propane ketone] composition group in one or more；
The UV absorbers are selected from hydroxyl phenol and triazine, the tert-amyl phenols of 2- (2H- BTA -2- bases) -4,6- two
With 6- methylheptyls 2- { 4- [4,6- bis- (4- xenyls) -1,3,5- triazine -2- bases] -3- hydroxyphenoxies } propionic ester composition
One or more in group；
The light stabilizer is selected from decanedioic acid methyl isophthalic acid, 2,2,6,6- pentamethyl -4- piperidine esters, two [2,2,6,6- tetramethyls -1-
(octyl group epoxide) -4- piperidyls] sebacate and it is poly- [6- [(1,1,3,3- tetramethyl butyls) amino]] -1,3,5- triazine -2,
4- [(2,2,6,6,-tetramethyl-4-piperidyl) imino group] -1,6- oneself two support [(2,2,6,6- tetramethyl -4- piperidyls) imido
Base] } composition group in one or more；
The antioxidant is selected from hydroquinone dibenzyl ether, β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid octadecanol fat
With the one or more in the group of four [β-(3,5- di-tert-butyl-hydroxy phenyls) propionic acid] pentaerythritol esters composition.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104263304A (en) * | 2014-10-11 | 2015-01-07 | 瑞洲树脂（东莞）有限公司 | Photocuring filling gel and application method |
-
2015
- 2015-09-18 CN CN201510599894.5A patent/CN105111998B/en active Active
Patent Citations (1)
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