WO2013013598A1 - Adhesive composition - Google Patents
Adhesive composition Download PDFInfo
- Publication number
- WO2013013598A1 WO2013013598A1 PCT/CN2012/078934 CN2012078934W WO2013013598A1 WO 2013013598 A1 WO2013013598 A1 WO 2013013598A1 CN 2012078934 W CN2012078934 W CN 2012078934W WO 2013013598 A1 WO2013013598 A1 WO 2013013598A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- weight
- percent
- adhesive composition
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 89
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 89
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 80
- 239000000178 monomer Substances 0.000 claims abstract description 50
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 239000003063 flame retardant Substances 0.000 claims abstract description 6
- 239000002562 thickening agent Substances 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000000996 additive effect Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- -1 2-ethylhexyl Chemical group 0.000 claims description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 238000010030 laminating Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Chemical group 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- QGZHYFIQDSBZCB-UHFFFAOYSA-N (2-ethylphenyl)-(2,4,6-trimethylbenzoyl)phosphinic acid Chemical compound CCC1=CC=CC=C1P(O)(=O)C(=O)C1=C(C)C=C(C)C=C1C QGZHYFIQDSBZCB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-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
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 2
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 claims description 2
- MZRQZJOUYWKDNH-UHFFFAOYSA-N diphenylphosphoryl-(2,3,4-trimethylphenyl)methanone Chemical compound 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical group CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 17
- 238000012360 testing method Methods 0.000 description 40
- 230000032683 aging Effects 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000001029 thermal curing Methods 0.000 description 10
- 238000003848 UV Light-Curing Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 238000009472 formulation Methods 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
Definitions
- Photo initiator 4-2 1.0 percent by weight
- Photoinitiator 4-2 1.0 percent by weight
- the percents of each component are percents by weight based on the total weight of the adhesive composition.
- the comparative adhesive composition 3 is formulated according to the following composition and the method of example 1.
- Component 1 Urethane oligomer carrying 60 0 percent by weight (meth)acryloyloxy group 1-1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The present invention relates to an adhesive composition, which comprises, based on the total weight of the adhesive composition: (1) from 38.0 to 75.0 percent by weight of a urethane oligomer carrying (meth)acryloyloxy group; (2) from 0.1 to 10.0 percent by weight of a multifunctional (meth)acrylate monomer; (3) from 15.0 to 60.0 percent by weight of a monofunctional (meth)acrylate monomer; (4) from 0.5 to 5.0 percent by weight of a photoinitiator; (5) from 0.1 to 5.0 percent by weight of a silane coupling agent; and (6) from 0 to 5.0 percent by weight of an additive, which is selected from one or more of the group consisting of a tackifier, a thickening agent, a flame retardant, a leveling agent and a thermal initiator. The cured adhesive composition has a high transparency and a high bonding strength, and the adhesive composition can be used for bonding various substrates in display devices.
Description
Adhesive composition
Field of the Invention
The present invention relates to an adhesive composition, which can be used for bonding various substrates in display devices.
Background Art
With the development of display devices, such as touch panels, new adhesives that can be used in those display devices are highly demanded. The adhesives should fulfill different requirements, e.g. the adhesive should be easily applied, easily cured, and should have a good transparency and good adhesion. Currently, the adhesives used for touch panels mostly are adhesive tapes. However, the optical transparency of adhesive tapes is not good. Thus, liquid adhesives for touch panels are developed to replace the adhesive tapes.
US 2010/0003425 Al discloses a method of producing an image display device, comprising the step of forming a cured resin layer by interposing a photo-curable resin composition between an image display unit and a light-transmitting protection member, wherein the resin composition contains a polymer selected from the group consisting of a polyurethane acrylate, a polyisoprene acrylate, and a terpene resin etc.
WO 2010/111316 A2 discloses an optical assembly having a display panel and methods of making and disassembling the same. WO 2010/111316 A2 uses an adhesive layer to bond a display panel and a substantially transparent substrate, wherein the adhesive layer comprises the reaction product of a multifunctional urethane (meth)acrylate oligomer and a reactive diluent comprising a monofunctional (meth)acrylate monomer, and an oil.
The adhesives disclosed in the above-mentioned prior art references have common defects, for example, the bonding effects between uneven surfaces of substrates are unsatisfying, the transparency is not high or the bonding strength is not strong enough.
Consequently, it is necessary to develop an adhesive composition, which has a high transparency and a high bonding strength after being cured, wherein the adhesion does not fail or bubbles do not occur in the adhesive composition even under severe conditions, such as in the large temperature range of -40 to 70°C and under high humidity conditions, and thus the performances of the adhesive and the final product are improved.
Summary of the Invention
The present invention provides an adhesive composition, which can be cured by UV irradiation, and the cured adhesive has a very high bonding strength, a very high flexibility and a very high elongation at break, and the parts adhered with the adhesive have excellent performance of preventing the occurrence of cracks under aging conditions.
The adhesive composition of the present invention comprises, based on the total weight of the adhesive composition:
(1) from 38.0 to 75.0 percent by weight of a urethane oligomer carrying (meth)acryloyloxy group;
(2) from 0.1 to 10.0 percent by weight of a multifunctional (meth)acrylate monomer;
(3) from 15.0 to 60.0 percent by weight of a mono functional (meth)acrylate monomer;
(4) from 0.5 to 5.0 percent by weight of a photoinitiator;
(5) from 0.1 to 5.0 percent by weight of a silane coupling agent; and
(6) optional an additive selected from one or more of the group consisting of a tackifier, a thickening agent, a flame retardant, a leveling agent and a thermal initiator.
In another aspect the present invention relates to the cured product of the adhesive of the present invention and to display devices which comprise said cured product.
In further aspects the present invention relates to the use of the adhesive of the present invention for bonding or laminating parts in display devices and to the use of said adhesive for assembling transparent parts.
Detailed Description of the Invention
All technical terms and scientific terms used herein have the same meanings as those commonly understood by those skilled in the art, unless indicated otherwise. In case that the meanings understood by those skilled in the art conflict with the meanings defined herein, the meanings defined herein shall be used as the criterion.
All percentages, parts, proportions and the like mentioned herein are based on weight.
When an amount, a concentration or other values or parameters is/are expressed in form of a range, a preferable range, or a preferable upper limit value and a preferable lower limit value, it should be understood as that any ranges obtained by combining any upper limit or preferable value with any lower limit or preferable value are specifically disclosed, without considering whether the obtained ranges are clearly mentioned in the context. The numerical ranges mentioned herein are meant to include both end values of the ranges and also all integers or fractions included in the ranges, unless indicated otherwise.
Each component of the adhesive composition of the invention will be described as
follows.
Urethane oligomer carrying (meth)acryloyloxy group
The urethane oligomer carrying (meth)acryloyloxy group is a urethane oligomer carrying one or more (meth)acryloyloxy group(s).
The term "(meth)acryloyloxy", as used herein, refers to both acryloyloxy and methacryloyloxy.
The average functionality of the urethane oligomer carrying (meth)acryloyloxy group is < 2. The term "average functionality", as used herein, means the average number of the (meth)acryloyloxy group(s) per molecule of the oligomer.
The urethane oligomer carrying (meth)acryloyloxy group preferably has a glass transition temperature (Tg) of from -80 °C to 0°C , more preferably from -60 °C to 0 °C .
The urethane oligomer carrying (meth)acryloyloxy group preferably has a Brookfield viscosity of from 1000 mPa-s to 190000 mPa-s at 25 °C , more preferably from 2000 mPa s to 150000 mPa s.
The amount of the urethane oligomer carrying (meth)acryloyloxy group in the adhesive composition of the present invention is from 38.0 to 75.0 percent by weight, preferably, from 40.0 to 65.0 percent by weight.
(Meth)acrylate monomer
The (meth)acrylate monomer includes monofunctional (meth)acrylate monomers and multifunctional (meth)acrylate monomers.
The term "(meth)acrylate", as used herein, refers to both acrylate and methacrylate.
The monofunctional (meth)acrylate monomer can be selected from monofunctional alkyl (meth)acrylates, monofunctional alkenyl (meth)acrylates, and monofunctional heterocyclo (meth)acrylates, wherein said alkyl is an alkyl group having from 1 to 20 carbon atoms, which may have one or more substituents; said alkenyl is an alkenyl group having from 2 to 20 carbon atoms, which may have one or more substituents; and said heterocyclo is a heterocyclic group having from 2 to 20 carbon atoms and having a heteroatom selected from nitrogen and oxygen, which may have one or more substituents; said one or more substituents may be selected from an alkyl group having from 1 to 20 carbon atoms, an alkyloxy group having from 1 to 20 carbon atoms, an aryloxy group having from 6 to 20 carbon atoms, a cyclalkyloxy group having from 3 to 20 carbon atoms, and hydroxyl.
The multifunctional (meth)acrylate monomer can be selected from multifunctional alkyl (meth)acrylates, multifunctional alkenyl (meth)acrylates, and multifunctional heterocyclo (meth)acrylates, wherein said alkyl is an alkyl group having from 1 to 20 carbon atoms, which may have one or more substituents; said alkenyl is an alkenyl group having from 2 to 20 carbon atoms, which may have one or more substituents; and said heterocyclo is a heterocyclic group having from 2 to 20 carbon atoms and having a heteroatom selected from nitrogen and oxygen, which may have one or more substituents; said one or more substituents may be selected from an alkyl group having from 1 to 20 carbon atoms, an alkyloxy group having from 1 to 20 carbon atoms, an aryloxy group having from 6 to 20 carbon atoms, a cycloalkyloxy group having from 3 to 20 carbon atoms, and hydroxyl.
Representative examples of the (meth)acrylate monomer include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-(2-ethoxyethoxy) ethyl acrylate, tetrahydrofurfury (meth)acrylate, lauryl acrylate, isooctyl acrylate, isodecyl acrylate, 2-phenoxyethyl acrylate, 2-ethylhexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentadienyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, caprolactone acrylate, morpholine (meth)acrylate, hexanediol di(meth)acrylate, ethyleneglycol dimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate and combinations thereof.
In the adhesive composition of the present invention, the monofunctional (meth)acrylate monomer or the multifunctional (meth)acrylate monomer can be used alone, or used in any combination thereof.
The amount of the monofunctional (meth)acrylate monomer in the adhesive composition of the present invention is from 15.0 to 60.0 percent by weight, preferably, from 20.0 to 45.0 percent by weight, and the amount of the multifunctional (meth)acrylate monomer is from 0.1 to 10.0 percent by weight, preferably, from 2.0 to 8.0 percent by weight.
Photoinitiator
There is no special limitation on the photoinitiators in the present invention. The photoinitiators generally used are benzil ketals, hydroxy ketones, amino ketones and acyl phosphine peroxides. Suitable photoinitiators include but are not limited to 2,2-dimethoxy-l,2-diphenylethan-l-one, trimethylbenzoyl diphenylphosphine oxide, 1 -hydroxycyclohexyl benzophenone, 2-methyl- 1 - [4-(methylthio)phenyl] -2 -morpholinopropan- 1 -one, ethyl-2,4,6-trimethylbenzoylphenylphosphinate, 2-hydroxyl-2-methyl- 1 -phenyl- 1 -propanone, diphenyl(2,4,6-trimethylbenzoyl)- phosphine oxide and combinations thereof. In the examples of the present invention, the photoinitiators of hydroxy ketones and acyl phosphine oxides are used as the photoinitiators. One or more initiators can be used in the adhesive of the present invention.
The amount of the photoinitiator in the adhesive composition of the present invention is from 0.5 to 5.0 percent by weight, preferably from 2.0 to 4.0 percent by weight.
Silane coupling agent
The silane coupling agent is a liquid silane having an organic group, wherein more than one alkoxy group is bonded to the silicon atom at one end of the molecule. The silane coupling agent can react with the surface of inorganic materials. The silane coupling agent further comprises a reactive group at the other end of the molecule which can chemically interact with a resin, e.g., a vinyl resin, an epoxy resin etc. The silane coupling agent can be obtained by the catalyzed addition of HS1CI3 to unsaturated alkenes with reactive groups in the presence of chloroplatinic acid followed by alcoho lysis.
The amount of the silane coupling agent in the adhesive composition of the present invention is from 0.1 to 5.0 percent by weight, preferably, from 2.0 to 4.0 percent by weight.
Optional additives
Optional additives in the adhesive of the present invention are selected from one or more of the group consisting of a tackifier, a thickening agent, a flame retardant, a leveling agent and a thermal initiator.
Tackifiers can enhance the initial bonding force produced between an adhesive and a surface of a material to be bonded, and improve the bonding force. Tackifiers can be resins, such as rosin resins, terpene resins such as Rosin731D (from Hercules Chemical Company, Inc.), phenol-formaldehyde resins, rubbers, such as polybutadiene, polyisoprene, fatty alcohols, e.g., poiyether poiyois.
Thickening agents can improve the viscosity of an adhesive system, adjust the rheologic behavior, and thicken the adhesive system. Thickening agent may be selected from fumed silica, rubber, cellulose etc.
Flame retardants can keep an adhesive from igniting or slow down the spread of flame and restrain smoke effectively. Flame retardants can be halogen-free phosphates such as dimethyl methylphosphonate (e.g., Fyrol DMMP from MultiChem Inc.), poiyether polyol phosphite, triphetiyl phosphate, cyclic phosphate.
Leveling agents help to achieve a flat, smooth and even state when a liquid is coated on a substrate. Leveling agenst can be polyacrylates, alkyl polysiloxanes, for example, BYK378 (from BYK (TONGLING) CO. LTD.).
Thermal initiators (organic peroxides) can achieve thermally-initiated curing. Organic peroxides can be peroxy(di)carbonates such as di(2-ethylhexyl) peroxydicarbonate,
diacyl peroxides such as dilauroyl peroxide, dialkyl peroxides such as 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, l-di(tert-butylperoxy)-3,3,5- trimethylhexa-ne, peroxyesters such as tert-butyl peroxybenzoate. In the adhesive of the present invention one or more peroxide thermal initiators can be used. In the present invention, ester peroxides and alkyl peroxides are adopted to achieve thermal curing.
The adhesive composition of the present invention can be used for bonding or laminating various substrates such as various parts in display devices, particularly for assembling transparent parts, or bonding or laminating transparent substrates, and bonding or laminating transparent substrate and opaque substrate. For example, the tra sparent substrate is glass or a transparent plastic substrate etc, and the opaque substrate is a metal, opaque plastic, ceramic, stone, leather or a wood substrate. Most preferably, the adhesive of the invention is used for laminating glass substrates or for bonding two glass substrates,
Examples
The present invention will be described in details in the following by way of examples. However, the protection scope of the present invention is not limited to these examples.
Materials used in the examples
Urethane oligomer carrying (meth)acryloyloxy group 1-1 :
Genomer 4188/EHA (from Rahn AG), average functionality: 1, Brookfield viscosity at 25°C: 100000 to 140000mPa-s, Tg= -17°C ;
Urethane oligomer carrying (meth)acryloyloxy group 1-2:
CN 9021 (from Sartomer Company, Inc.), average functionality: 2, Brookfield viscosity at 25°C: 32000 mPa-s, Tg = -54°C;
Multifunctional acrylate monomer 2:
Pe iaerythritol tetraaery!ate (multifunctional) (from Sartomer Company, Inc.)
Mono functional acrylate monomer 3-1 :
Hydroxypropyl methacrylate (from Sigma- Aldrich Co. LLC)
Mono functional acrylate monomer 3-2:
2-(2-ethoxyethoxy) ethyl acrylate (from Sartomer Company, Inc.) Photoinitiator 4-1 :
2-hydroxyl-2-methyl-l -phenyl- 1-propanone (from BASF company, Inc.) Photoinitiator 4-2:
Diphenyl(2,4,6-trimethylbenzoyl)-phosphine oxide (from BASF company, Inc.)
Silane coupling agent 5 :
Z-6011 (from Dow Corning Corporation);
Thermal initiator 6:
l,l-di(tert-butylperoxy)-3,3,5-trimethylhexane (from J&K Scientific Ltd.).
Other compounds used in the examples are all chemical pure agents that are commercially available.
Test Methods and conditions:
♦ Test of UV curing: The adhesive composition between glass and PC is irradiated by UV light source with an irradiation power of lOOmW/cm and a wavelength of 200nm to 400nm at room temperature.
♦ Test of thermal curing: Away from the light, the adhesive composition between glass and PC is thermally cured in an oven (80°C, lhr).
♦ Test of thermal impact: The adhesive is placed on glass/PMMA, and is subjected to thermal impact at high temperature and low temperature of -40~70°C for lhr respectively by a conventional thermal impact device, and the cycling time is 240 hrs.
♦ Test of aging under high humidity: high humidity conditions (60°C&90%RH, 240hrs, glass/PMMA)
♦ Test of measuring the bonding strength: The test aims at charactering the bonding strength imparted by the sufficiently cured adhesive to two substrates . The cured thickness is generally controlled to be ΙΟΟμιη according to practical requirements. The substrates can be glass plates, polyester plates, or acrylic plates. The measurement device can be a universal tensile testing machine. The bonding strength measurement is conducted to the cued sample by pulling the two plates apart in the directions perpendicular to the surfaces by using a universal tensile testing machine. The strength (unit: MPa) is calculated by dividing the force needed to pull the two plates apart by the contact area of the two plates. In the present invention, after the adhesive composition between a glass plate and a PMMA plate cured by irradiating UV light having a UVA magnitude of lOOmW/cm for 30 s, the bonding strength of the adhesive composition is measured.
♦ Test of transparency: The transparency of the cured adhesive is measured by a UV spectrophotometer. The cured thickness of the adhesive is controlled to be ΙΟΟμιη by two glass plates. The test method is in accordance with ASTM D 1003-2007. After the adhesive composition between a glass plate and a glass plate is cured by irradiating UV light having a UVA magnitude of lOOmW/cm for 30 s, the transparency of the adhesive composition is measured.
♦ Test of elongation at break: The test method is in accordance with ASTM D638, and the moving speed of clamps is 50mm/min.
Example 1
The adhesive composition 1 is formulated according to the following composition and method.
Component 1 Urethane oligomer carrying 65.0 percent by weight
(meth)acryloyloxy group 1-2
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 15.0 percent by weight
Mono functional acrylate monomer 3-2 15.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 5 Silane coupling agent 5 1.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
Formulation method
Each of the above components (lOOg in total) are weighted into a plastic barrel having a capacity of 150g, and dispersed at a high speed of from 2000 to 2400 rpm for 4 minutes using a SpeedMixer™ mixer from FlackTech Inc. Thereby, the adhesive composition 1 is obtained.
The obtained adhesive composition 1 was cured within 30 s in the test of UV curing, and can not be cured in the test of thermal curing. No bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength :>1.0MPa, transparency: >92%, elongation at break: 300%.
Example 2
The adhesive composition 2 is formulated according to the following composition and the formulation method of example 1.
Component 1 Urethane oligomer carrying 60.0 percent by weight
(meth)acryloyloxy group 1-1
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 17.0 percent by weight mono functional acrylate monomer 3-2 16.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 5 Silane coupling agent 5 1.0 percent by weight
Component 6 Thermal initiator 6 2.0 percent by weight
The percents of each component are percents by weight based on the total weight of
the adhesive composition.
The obtained adhesive composition 2 was cured within 30 s in the test of UV curing, and can be cured in the test of thermal curing. No bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength: >1.0MPa, transparency: >92%, elongation at break: 800%.
Example 3
The adhesive composition 3 is formulated according to the following composition and the formulation method of example 1.
Component 1 Urethane oligomer carrying 60.0 percent by weight
(meth)acryloyloxy group 1-1
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 17.0 percent by weight
Mono functional acrylate monomer 3-2 18.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photo initiator 4-2 1.0 percent by weight
Component 5 Silane coupling agent 5 1.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
The obtained adhesive composition 3 was cured within 30 s in the test of UV curing, and can not be cured in the test of thermal curing. No bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength: >1.0MPa, transparency: >92%, elongation at break: 800%.
Example 4
The adhesive composition 4 is formulated according to the following composition and the formulation method of example 1.
Component 1 Urethane oligomer carrying 50.0 percent by weight
(meth)acryloyloxy group 1-1
Component 2 Multifunctional acrylate monomer 2 2.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 24.0 percent by weight mono functional acrylate monomer 3-2 20.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 5 Silane coupling agent 5 1.0 percent by weight
The percents of each component are percents by weight based on the total weight of
the adhesive composition.
The obtained adhesive composition 4 was cured within 30 s in the test of UV curing, and can not be cured in the test of thermal curing. No bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength: >0.8MPa, transparency: >92%, elongation at break: 400%.
Example 5
The adhesive composition 5 is formulated according to the following composition and the formulation method of example 1.
Component 1 Urethane oligomer carrying 50.0 percent by weight
(meth)acryloyloxy group 1-1
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 22.0 percent by weight
Mono functional acrylate monomer 3-2 21.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 5 Silane coupling agent 5 1.0 percent by weight
Component 6 Thermal initiator 6 2.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
The obtained adhesive composition 5 was cured within 30 s in the test of UV curing, and can be cured in the test of thermal curing. No bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength: >1.2MPa, transparency: >92%, elongation at break: 800%.
Comparative example 1
The comparative adhesive composition 1 is formulated according to the following composition and the method of example 1.
Component 1 Urethane oligomer carrying 35.0 percent by weight
(meth)acryloylxy group 1-1
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 35.0 percent by weight
Mono functional acrylate monomer 3-2 24.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 6 Thermal initiator 6 2.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
The obtained comparative adhesive composition 1 was cured within 30 s in the test of UV curing, and can be cured in the test of thermal curing. Bubbles occurred in the test of thermal impact, and no cracks occurred in the test of aging under high humidity. The bonding strength: >1.0MPa, transparency: >92%, elongation at break: 70%.
The results show that when component 1-1 is 35.0 percent by weight, partial failure may occur due to aging, and elongation at break decreased to 70 percent remarkably.
Comparative example 2
The comparative adhesive composition 2 is formulated according to the following composition and the method of example 1.
Component 1 Urethane oligomer carrying 60.0 percent by weight
(meth)acryloyloxy group 1-1
Component 2 Multifunctional acrylate monomer 2 1.0 percent by weight
Component 3 Mono functional acrylate monomer 3-1 17.0 percent by weight
Mono functional acrylate monomer 3-2 17.0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1.0 percent by weight
Component 6 Thermal initiator 6 2.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
The obtained comparative adhesive composition 2 was cured within 30 s in the test of UV curing, and can be cured in the test of thermal curing. Bubbles occurred in the test of thermal impact, and cracks occurred slightly in the test of aging under high humidity. The bonding strength: >0.8MPa, transparency: >92%, elongation at break: 800%.
The results show that when none silane coupling agent was added, failure may occur due to aging.
Comparative example 3
The comparative adhesive composition 3 is formulated according to the following composition and the method of example 1.
Component 1 Urethane oligomer carrying 60 0 percent by weight (meth)acryloyloxy group 1-1
Component 3 Mono functional acrylate monomer 3-1 18 0 percent by weight
Mono functional acrylate monomer 3-2 16 0 percent by weight
Component 4 Photoinitiator 4-1 2.0 percent by weight
Photoinitiator 4-2 1 0 percent by weight
Component 5 Silane coupling agent 5 1 0 percent by weight Component 6 Thermal initiator 6 2.0 percent by weight
The percents of each component are percents by weight based on the total weight of the adhesive composition.
The obtained comparative adhesive composition 3 was cured within 30 s in the test of UV curing, and can be cured in the test of thermal curing. Bubbles occurred in the test of thermal impact, and cracks occurred slightly in the test of aging under high humidity. The bonding strength: >1.0MPa, transparency: >92%, elongation at break:
800%.
Claims
1. An adhesive composition comprising, based on the total weight of the adhesive composition:
(1) from 38.0 to 75.0 percent by weight of a urethane oligomer carrying (meth)acryloyloxy group;
(2) from 0.1 to 10.0 percent by weight of a multifunctional (meth)acrylate monomer;
(3) from 15.0 to 60.0 percent by weight of a monofunctional (meth)acrylate monomer;
(4) from 0.5 to 5.0 percent by weight of a photoinitiator;
(5) from 0.1 to 5.0 percent by weight of a silane coupling agent; and
(6) from 0 to 5.0 percent by weight of an additive, which is selected from one or more of the group consisting of a tackifier, a thickening agent, a flame retardant, a leveling agent and a thermal initiator.
2. The adhesive composition according to claim 1, wherein the urethane oligomer carrying (meth)acryloyloxy group has an average functionality of the (meth)acryloyloxy group of no more than 2.
3. The adhesive composition according to claim 1, wherein urethane oligomer carrying (meth)acryloyloxy group has a Tg of from -80°C to 0°C, preferably, from -60°C to 0°C, and the urethane oligomer carrying (meth)acryloyloxy group has a Brookfield viscosity at 25°C of from 1000 mPa-s to 190000 mPa-s, preferably, from 2000 mPa-s to 150000 mPa-s.
4. The adhesive composition according to claim 1, wherein the amount of the urethane oligomer carrying (meth)acryloyloxy group is from 40.0 to 65.0 percent by weight.
5. The adhesive composition according to claim 1, wherein the monofunctional (meth)acrylate monomer is selected from monofunctional alkyl (meth)acrylates, monofunctional alkenyl (meth)acrylates, and monofunctional heterocyclo (meth)acrylates,
wherein said alkyl is an alkyl group having from 1 to 20 carbon atoms, which may have one or more substituents; said alkenyl is an alkenyl group having from 2 to 20 carbon atoms, which may have one or more substituents; and said heterocyclo is a heterocyclic group having from 2 to 20 carbon atoms and having a heteroatom selected from nitrogen and oxygen, which may have one or more substituents; said one or more substituents may be selected from an alkyl group having from 1 to 20 carbon atoms, an alkyloxy group having from 1 to 20 carbon atoms, an aryloxy group having from 6 to 20 carbon atoms, a cycloalkyloxy group having from 3 to 20 carbon atoms, and hydroxyl.
6. The adhesive composition according to claim 1, wherein the monofunctional (meth)acrylate monomer is selected from methyl (meth)acrylate, ethyl (meth)acrylate, butyl (methyl)acrylate, 2-(2-ethoxyethoxy) ethyl acrylate, tetrahydrofurfury (meth)acrylate, lauryl acrylate, isooctyl acrylate, isodecyl acrylate, 2-phenoxyethyl acrylate, 2-ethylhexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentadienyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, caprolactone acrylate, morpholine (meth)acrylate and combinations thereof.
7. The adhesive composition according to claim 1, wherein the multifunctional (me th) acrylate monomer is selected from multifunctional alkyl (meth)acrylates, multifunctional alkenyl (meth)acrylates, and multifunctional heterocyclo (meth)acrylates,
wherein said alkyl is an alkyl group having from 1 to 20 carbon atoms, which may have one or more substituents; said alkenyl is an alkenyl group having from 2 to 20 carbon atoms, which may have one or more substituents; and said heterocyclo is a heterocyclic group having from 2 to 20 carbon atoms and having a heteroatom selected from nitrogen and oxygen, which may have one or more substituents; said one or more substituents may be selected from an alkyl group having from 1 to 20 carbon atoms, an alkyloxy group having from 1 to 20 carbon atoms, an aryloxy group having from 6 to 20 carbon atoms, a cycloalkyloxy group having from 3 to 20 carbon atoms, and hydroxyl.
8. The adhesive composition according to claim 1, wherein the multifunctional (meth)acrylate monomer is selected from hexanediol di(meth)acrylate, ethyleneglycol dimethacrylate, trimethylolpropane triacrylate, perstaer thr toi tetraacrylate and combinations thereof.
9. The adhesive composition according to claim 1, wherein the amount of the monofunctional (me th) acrylate monomer is from 20.0 to 45.0 percent by weight, and the amount of the multifunctional (meth) acrylate monomer is from 2.0 to 8.0 percent by weight.
10. The adhesive composition according to claim 1, wherein the photoinitiator is selected from 2,2-dimethoxy-l,2-diphenylethan-l-one,
trimethylbenzoyl diphenylphosphine oxide, 1-hydroxycyclohexyl benzophenone,
2-methyl-l-[4-(methylthio)phenyl]-2-morpholinopropan-l-one,
ethyl-2,4,6-trimethylbenzoylphenylphosphinate,
2-hydroxyl-2-methyl-l -phenyl- 1-propanone, diphenyl(2,4,6-trimethylbenzoyl)- phosphine oxide and combinations thereof, and the amount of the photo initiator is from 2.0 to 4.0 percent by weight.
11. A cured product of the adhesive of any one of claims 1 to 10.
12. The cured product of claim 11, wherein the product is obtained by exposing the adhesive of any one of claims 1 to 10 to UV radiation.
13. A display device comprising the cured product of claim 11 or 12.
14. Use of an adhesive of any one of claims 1 to 10 for bonding or laminating parts in display devices.
15. Use of an adhesive of any one of claims 1 to 10 for assembling transparent parts.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201280036183.1A CN104271697B (en) | 2011-07-25 | 2012-07-20 | Adhesive composition |
| JP2014521925A JP6095069B2 (en) | 2011-07-25 | 2012-07-20 | Adhesive composition |
| KR1020147002069A KR102038160B1 (en) | 2011-07-25 | 2012-07-20 | Adhesive composition |
| EP12818089.0A EP2736998A4 (en) | 2011-07-25 | 2012-07-20 | Adhesive composition |
| US14/162,301 US20140142210A1 (en) | 2011-07-25 | 2014-01-23 | Adhesive composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110211101.XA CN102898958B (en) | 2011-07-25 | 2011-07-25 | A kind of adhesive composition |
| CN201110211101.X | 2011-07-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/162,301 Continuation US20140142210A1 (en) | 2011-07-25 | 2014-01-23 | Adhesive composition |
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| Publication Number | Publication Date |
|---|---|
| WO2013013598A1 true WO2013013598A1 (en) | 2013-01-31 |
Family
ID=47571455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2012/078934 WO2013013598A1 (en) | 2011-07-25 | 2012-07-20 | Adhesive composition |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20140142210A1 (en) |
| EP (1) | EP2736998A4 (en) |
| JP (1) | JP6095069B2 (en) |
| KR (1) | KR102038160B1 (en) |
| CN (2) | CN102898958B (en) |
| TW (1) | TWI553081B (en) |
| WO (1) | WO2013013598A1 (en) |
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| EP2742108A1 (en) * | 2011-08-12 | 2014-06-18 | Henkel (China) Co. Ltd. | Optical transparent dual cure adhesives composition |
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| US10717907B2 (en) | 2014-11-18 | 2020-07-21 | Henkel Ag & Co. Kgaa | Photo-curable adhesive composition, preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI553081B (en) | 2016-10-11 |
| US20140142210A1 (en) | 2014-05-22 |
| KR20140058513A (en) | 2014-05-14 |
| CN104271697A (en) | 2015-01-07 |
| CN102898958B (en) | 2016-11-02 |
| JP2014523472A (en) | 2014-09-11 |
| JP6095069B2 (en) | 2017-03-15 |
| EP2736998A1 (en) | 2014-06-04 |
| EP2736998A4 (en) | 2015-09-16 |
| CN104271697B (en) | 2017-08-01 |
| KR102038160B1 (en) | 2019-10-29 |
| TW201305303A (en) | 2013-02-01 |
| CN102898958A (en) | 2013-01-30 |
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