CN110234506B - Method for producing laminate and photocurable resin composition - Google Patents
Method for producing laminate and photocurable resin composition Download PDFInfo
- Publication number
- CN110234506B CN110234506B CN201880010675.0A CN201880010675A CN110234506B CN 110234506 B CN110234506 B CN 110234506B CN 201880010675 A CN201880010675 A CN 201880010675A CN 110234506 B CN110234506 B CN 110234506B
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- CN
- China
- Prior art keywords
- resin composition
- acrylate
- heating
- meth
- laminate according
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 227
- 238000004519 manufacturing process Methods 0.000 title claims description 27
- 238000010438 heat treatment Methods 0.000 claims abstract description 76
- 239000000178 monomer Substances 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 238000000576 coating method Methods 0.000 claims abstract description 25
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- 230000001678 irradiating effect Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 18
- -1 isostearyl Chemical group 0.000 claims description 18
- 239000004014 plasticizer Substances 0.000 claims description 18
- 239000004925 Acrylic resin Substances 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 7
- 239000010419 fine particle Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 4
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 claims description 3
- OVJHMJJVXOJMBB-UHFFFAOYSA-N 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)N(CCOC(=O)C=C)C(=O)C21 OVJHMJJVXOJMBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N ortho-phenyl-phenol Natural products OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 3
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000004306 orthophenyl phenol Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 22
- 239000000945 filler Substances 0.000 abstract description 18
- 239000000203 mixture Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000011521 glass Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000011049 filling Methods 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 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 5
- 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 5
- 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 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920001195 polyisoprene Polymers 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
- C03C27/06—Joining glass to glass by processes other than fusing
- C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/12—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by mechanical means
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B2037/1253—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2310/00—Treatment by energy or chemical effects
- B32B2310/08—Treatment by energy or chemical effects by wave energy or particle radiation
- B32B2310/0806—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation
- B32B2310/0831—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation using UV radiation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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- 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
- C09J2433/00—Presence of (meth)acrylic polymer
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/133308—Support structures for LCD panels, e.g. frames or bezels
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/28—Adhesive materials or arrangements
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Geochemistry & Mineralogy (AREA)
- General Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mechanical Engineering (AREA)
- Theoretical Computer Science (AREA)
- Plasma & Fusion (AREA)
- Wood Science & Technology (AREA)
- Laminated Bodies (AREA)
- Liquid Crystal (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Joining Of Glass To Other Materials (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Even when resin compositions having the same composition are used as the bank material and the filler, the high viscosity of the bank material and the low viscosity of the filler can be compatible with each other, and the adhesion between the members can be improved. The preparation method comprises the following steps: a step (A) of forming a coating region (7) of a 2 nd resin composition (8) on the surface of a 1 st member by using a 1 st resin composition; a step (B) of applying a 2 nd resin composition 8 to the application region 7; a step (C) of bonding the 1 st member and the 2 nd member via the 2 nd resin composition to fill the coating region 7 with the 2 nd resin composition 8; and a step (D) of irradiating the 2 nd resin composition 8 with light to form a cured resin layer 1. The step (C) includes heating the 2 nd resin composition 8. The 2 nd resin composition 8 contains a monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes. The residual heating amount of the 2 nd resin composition 8 after heating at 80 ℃ for 3 hours was 95.0% or more.
Description
Technical Field
The present technology relates to a method for producing a laminate and a photocurable resin composition. The present application claims priority based on japanese patent application No. 2017-037614, filed in the japanese country on 28/2/2017, which is incorporated herein by reference.
Background
Conventionally, a technique of bonding members to each other with a photocurable resin composition and fixing them with a light-transmitting resin layer has been known. For example, patent document 1 describes a method in which a photocurable resin composition is disposed between an image display member and a light-transmissive member to form a resin composition layer, and light is irradiated on the resin composition layer to form a cured resin layer. Here, it is desirable that the adhesion between the light-transmissive member and the image display member in the image display device is good.
In addition, from the viewpoint of suppressing bleeding of the photocurable resin composition from a coated body (a light-transmitting member or an image display member), a so-called dam and fill process (dam and fill process) is sometimes employed. In the bank filling method, for example, a coating region of a 2 nd resin composition (filling material) is formed on the surface of the image display member using a 1 st resin composition (bank material). Next, a 2 nd resin composition is applied to the formed application region, and the image display member and the light-transmitting member are bonded via the 2 nd resin composition. Then, the 2 nd resin composition is irradiated with light to form a cured resin layer.
In the dam filling method, the dam material is preferably high in viscosity from the viewpoint of preventing dripping. On the other hand, the filler is preferably low in viscosity from the viewpoint of preventing air bubbles and attaching them in a short tact time. Here, in order to make the visibility of the boundary portion between the bank material and the filler good, that is, to make the boundary line between the bank material and the filler inconspicuous, the resin compositions of the same components may be used as the bank material and the filler. However, if resin compositions having the same components are used as the bank material and the filler, there is a fear that the high viscosity of the bank material and the low viscosity of the filler are sacrificed.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2014-222350.
Disclosure of Invention
Problems to be solved by the invention
The present technology has been made in view of the above-described conventional circumstances, and provides: a method for producing a laminate, which can achieve both high viscosity of a bank material and low viscosity of a filler and good adhesion between members, even when resin compositions having the same components are used as the bank material and the filler, and a photocurable resin composition.
Means for solving the problems
The method for producing a laminate according to the present technology comprises: a step (A) of forming a coating region of a 2 nd photocurable resin composition on the surface of a 1 st member using a 1 st resin composition, a step (B) of coating the 2 nd resin composition on the coating region, a step (C) of bonding the 1 st member and the 2 nd member via the 2 nd resin composition to fill the coating region with the 2 nd resin composition, and a step (D) of forming a cured resin layer by irradiating the 2 nd resin composition with light; the step (C) includes heating the 2 nd resin composition; the 2 nd resin composition contains a monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes; the residual heating amount of the 2 nd resin composition after heating at 80 ℃ for 3 hours is 95.0% or more.
The photocurable resin composition according to the present technology contains: a residual amount after heating at 60 ℃ for 30 minutes is 95.0% or more of a monofunctional monomer, (meth) acrylate resin, photopolymerization initiator, and plasticizer, and a residual amount after heating at 80 ℃ for 3 hours is 95.0% or more.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present technology, even when resin compositions having the same components are used as the 1 st resin composition (bank material) and the 2 nd resin composition (filler), the high viscosity of the bank material and the low viscosity of the filler can be both satisfied, and the adhesion between the members can be made good.
Drawings
Fig. 1 is a cross-sectional view showing an example of an image display device.
FIG. 2 is a front view showing an example of an image display part, and FIG. 2B is a sectional view A-A' shown in FIG. 2A.
FIG. 3A is a front view for explaining an example of a method for forming a coated region of a 2 nd resin composition on a surface of an image display member using a 1 st resin composition, and FIG. 3B is a sectional view A-A' shown in FIG. 3A.
FIG. 4 is a sectional view for explaining an example of a method for forming a coated region of a 2 nd resin composition on a surface of an image display member using the 1 st resin composition.
FIG. 5A is a front view for explaining an example of a method of applying the 2 nd resin composition, and FIG. 5B is a sectional view A-A' shown in FIG. 5A.
FIG. 6A is a front view showing an example of a method for bonding an image display member and a light-transmitting member via a 2 nd resin composition, and FIG. 6B is a sectional view taken along line A-A' shown in FIG. 6A.
FIG. 7 is a sectional view for explaining an example of a method of forming a cured resin layer by irradiating a 2 nd resin composition with light.
FIG. 8 is a view for explaining a method of measuring a residual amount of a monofunctional monomer after heating.
FIG. 9 is a view for explaining a method of measuring a residual heating amount of a photocurable resin composition.
FIG. 10 is a perspective view for explaining a measuring method of an adhesion strength test.
Fig. 11 is a sectional view of a-a' in fig. 10.
FIG. 12 is a perspective view for explaining a measuring method of an adhesion strength test.
Fig. 13 is a sectional view a-a' of fig. 12.
FIG. 14 is a perspective view for explaining a measuring method of an adhesion strength test.
Detailed Description
[ method for producing laminate ]
The method for producing a laminate according to the present embodiment includes the following steps (a) to (D), and the step (C) includes heating the 2 nd resin composition. In addition, as described in detail below, the 2 nd resin composition used in the present production method contains a monofunctional monomer whose heating residual amount after heating at 60 ℃ for 30 minutes is 95.0% or more, and whose heating residual amount after heating at 80 ℃ for 3 hours is 95.0% or more.
Step (A): a1 st resin composition is used to form a coating region of a 2 nd photocurable resin composition on the surface of a 1 st member.
A step (B): the 2 nd resin composition is coated on the coating area.
Step (C): the 1 st member and the 2 nd member are bonded via the 2 nd resin composition, so that the 2 nd resin composition fills the coating region.
A step (D): the 2 nd resin composition is irradiated with light to form a cured resin layer.
According to the present production method, the viscosity of the 2 nd resin composition can be reduced by heating the 2 nd resin composition in the step (C). Therefore, even when resin compositions having the same components are used as the 1 st resin composition and the 2 nd resin composition, the high viscosity of the 1 st resin composition and the low viscosity of the 2 nd resin composition can be compatible with each other. In addition, in the present production method, by using the 2 nd resin composition having a residual heating amount of 95.0% or more after heating at 80 ℃ for 3 hours, volatilization of components in the 2 nd resin composition can be suppressed when the 2 nd resin composition is heated, and thus the adhesion between the 1 st member and the 2 nd member can be made good.
The residual heating amount of the 2 nd resin composition used in the present production method after heating at 80 ℃ for 3 hours is 95.0% or more, preferably 97.0% or more, more preferably 98.0% or more, and still more preferably 99.0% or more. Since the heating residual amount is larger, volatilization of components in the 2 nd resin composition can be more effectively suppressed when the 2 nd resin composition is heated. In addition, the upper limit value of the heating residual amount of the 2 nd resin composition is not particularly limited. Here, the residual heating amount of the 2 nd resin composition is a value obtained by measuring the mass of 10mg of the resin composition before and after heating at 80 ℃ for 3 hours using a calorimeter measuring apparatus (apparatus name: Q50, manufactured by TA Instruments). Details of the 2 nd resin composition are described below.
The details of each step will be described below with reference to the drawings. In the present production method, for example, as shown in fig. 1, an image display member 2 (1 st member) and an image display device 5 (laminate) in which a light-transmitting member 3 (2 nd member) having a light-shielding layer 4 formed on the peripheral edge portion thereof are laminated via a cured resin layer 1 are obtained.
The cured resin layer 1 is formed from the following 1 st resin composition 6 and 2 nd resin composition 8. The refractive index of the cured resin layer 1 is preferably substantially the same as the refractive index of the image display member 2 and the translucent member 3, and is preferably 1.45 or more and 1.55 or less, for example. This improves the brightness and contrast of the image light from the image display unit 2, and improves the visibility. In addition, the transmittance of the cured resin layer 1 is preferably over 90%. This makes it possible to improve the visibility of the image formed on the image display member 2. The thickness of the cured resin layer 1 is preferably 50 to 200 μm, for example.
The image display unit 2 may be, for example, a liquid crystal display panel or a touch panel. Here, the touch panel refers to an image display/input panel combining a display element such as a liquid crystal display panel and a position input device such as a touch panel.
The light-transmitting member 3 may be any member having light-transmitting properties so that an image formed on the image display member 2 can be visually recognized. Examples of the material include a plate-like material or a sheet-like material such as glass, acrylic resin, polyethylene terephthalate, polyethylene naphthalate, and polycarbonate. These materials may be subjected to hard coat (hardcoat) treatment, antireflection treatment, or the like on at least one side. Physical properties such as the thickness and the elastic modulus of the light-transmitting member 3 can be determined as appropriate depending on the purpose of use.
The light shielding layer 4 is provided to improve the contrast of an image, and may be formed by applying a coating material colored black or the like by, for example, a screen printing method, drying, and curing. The thickness of the light-shielding layer 4 is usually 5 to 100 μm.
[ Process (A) ]
In the step (a), for example, as shown in fig. 2 and 3, the 1 st resin composition 6 is used to form the coating region 7 of the 2 nd resin composition 8 on the surface of the image display member 2. For example, as shown in fig. 3 and 4, the application region 7 is a region surrounded by a frame-shaped liquid stopper (liquid stopper め, bank) 11 formed of the 1 st resin composition 6 in the display region of the image display member 2.
The 1 st resin composition 6 is a material for preventing the 2 nd resin composition 8 applied to the application region 7 in the step (B) from dripping. The 1 st resin composition 6 may be a thermosetting resin composition, a photocurable (e.g., ultraviolet-curable) resin composition, or the like, for example. When the 1 st resin composition 6 is a photocurable resin composition, in the step (a), for example, as shown in fig. 4, the 1 st resin composition 6 is irradiated with ultraviolet rays 10 from an ultraviolet irradiator 9 to cure the 1 st resin composition 6, thereby forming a liquid stop portion 11, whereby the application region 7 can be defined.
From the viewpoint of preventing dripping, the 1 st resin composition 6 is preferably high in viscosity. For example, the viscosity of the 1 st resin composition 6 at 25 ℃ is preferably 10000 to 50000 mPas.
The coating method of the 1 st resin composition 6 may be any of various coating methods, and examples thereof include a method using a dispenser, a method using an applicator, and a method using a spray. Particularly, from the viewpoint of suppressing dripping, a method using a dispenser is preferable. The coating thickness of the 1 st resin composition 6 may be, for example, equal to or less than the thickness of the 2 nd resin composition 8 coated in the coating region 7 in the step (B) of the present production method.
[ Process (B) ]
In the step (B), for example, as shown in fig. 5, the 2 nd resin composition 8 is applied to the application region 7. As the coating method of the 2 nd resin composition 8, various coating methods can be adopted, and for example, the coating method of the 1 st resin composition 6 can be mentioned. The amount of the 2 nd resin composition 8 to be applied is preferably such an amount that the application region 7 can be filled when the bonding in the step (C) is performed, for example.
The 2 nd resin composition 8 is preferably such that, when cured in the step (D), a boundary line with the liquid stopper 11 formed of the 1 st resin composition 6 is not visually apparent. Therefore, the 2 nd resin composition 8 preferably contains substantially the same components as the 1 st resin composition 6. The same component means that at least the 1 st resin composition 6 and the 2 nd resin composition 8 have the same optical characteristics, for example, the light transmittance and the refractive index are substantially the same. In the case where the optical characteristics of the 1 st resin composition 6 and the 2 nd resin composition 8 are substantially the same, for example, even if the viscosities of the 1 st resin composition 6 and the 2 nd resin composition 8 are different, they are considered to be contained in the same component.
In addition, from the viewpoint of preventing air bubbles and bonding in a short takt time, the 2 nd resin composition 8 is preferably low in viscosity when bonding in the step (C) is performed. For example, the viscosity of the 2 nd resin composition 8 at the temperature at the time of bonding is preferably 3000 mPas or less, and more preferably 1000 to 3000 mPas.
In the present production method, the viscosity of the 2 nd resin composition 8 can be adjusted to a low viscosity (for example, 3000mPa · s or less) by heating (warming) the 2 nd resin composition 8 in the following step (C). Therefore, even when the same components of the resin compositions are used as the 1 st resin composition 6 and the 2 nd resin composition 8, the high viscosity of the 1 st resin composition 6 and the low viscosity of the 2 nd resin composition 8 can be compatible with each other.
In the present production method, by using the 2 nd resin composition 8 having a residual heating amount of 95.0% or more after heating at 80 ℃ for 3 hours, volatilization of components (for example, monofunctional monomers described below) in the 2 nd resin composition 8 can be suppressed when the 2 nd resin composition 8 is heated in the following step (C). Therefore, the adhesiveness between the light-transmissive member 3 and the image display member 2 can be made good.
[ Process (C) ]
In the step (C), for example, as shown in fig. 6, the image display member 2 and the light-transmitting member 3 are bonded via the 2 nd resin composition 8, and the 2 nd resin composition 8 is filled in the coating region 7. The bonding of the image display member 2 and the translucent member 3 can be performed using a known bonding device, for example.
In addition, as described above, the step (C) includes heating the 2 nd resin composition 8. By heating the 2 nd resin composition 8, the 2 nd resin composition 8 is filled in the coating region 7 in a visbroken state. This prevents bubbles in the 2 nd resin composition 8, and allows the bonding with a short tact time. The heating conditions are preferably set so that the viscosity of the 2 nd resin composition 8 is adjusted to a low viscosity (for example, 3000 mPas or less). For example, considering the influence of heat on the image display member 2 or the light-transmissive member 3, the heating temperature is preferably 80 ℃ or lower, and more preferably 60 to 80 ℃. The heating time may be, for example, about 30 minutes to 3 hours. The timing of heating may be performed before the image display member 2 and the light-transmissive member 3 are bonded, during bonding, or after bonding. Examples of the heating method include a method using a heater for heating.
[ Process (D) ]
In the step (D), as shown in fig. 7, for example, ultraviolet rays 10 are irradiated from an ultraviolet irradiator 9 to the 2 nd resin composition 8 to form a cured resin layer 1 (see fig. 1). The light irradiation in the step (D) is preferably performed after the heat of the 2 nd resin composition 8 heated in the step (C) is released.
Here, when the 2 nd resin composition 8 is substantially the same component as the 1 st resin composition 6, the 2 nd resin composition 8 after light irradiation is integrated with the liquid stopper portion 11 to form a single cured resin layer 1 having optically the same properties. This makes it possible to improve the visibility of the boundary between the liquid stopper 11 and the cured 2 nd resin composition 8.
As described above, according to the present production method, by heating the 2 nd resin composition 8 in the step (C), the viscosity of the 2 nd resin composition 8 is reduced. Therefore, even when the same components of the resin compositions are used as the 1 st resin composition 6 and the 2 nd resin composition 8, the high viscosity of the 1 st resin composition 6 and the low viscosity of the 2 nd resin composition 8 can be compatible with each other. In the present production method, as the 2 nd resin composition 8, a photocurable resin composition containing a monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes and having a residual heating amount of 95.0% or more after heating at 80 ℃ for 3 hours is used. This suppresses volatilization of the components in the 2 nd resin composition 8 when the 2 nd resin composition 8 is heated, and makes it possible to improve the adhesion between the light-transmissive member 3 and the image display member 2.
In the above production method, the 1 st resin composition 6 and the 2 nd resin composition 8 are applied to the surface of the image display member 2, but the method is not limited thereto. For example, the 1 st resin composition 6 and the 2 nd resin composition 8 may be applied to the surface of the light-transmissive member 3. In the above-described manufacturing method, the light-transmitting member 3 having the light-shielding layer 4 formed thereon is used, but the present invention is not limited to this example. For example, a light-transmitting member in which a light-shielding layer is not formed may be used.
In the step (a), the liquid stop portion 11 is formed by curing the photocurable resin composition 6 by light irradiation, but the method is not limited thereto. For example, in the step (a), the thermosetting 1 st resin composition 6 can be used, and the 1 st resin composition 6 is heated and cured to form the liquid stop portion 11. In addition, in the case where the viscosity of the 1 st resin composition 6 is sufficiently high to prevent dripping of the 2 nd resin composition 8, the 1 st resin composition 6 may not be cured by heat or light.
[ Photocurable resin composition ]
The photocurable resin composition according to the present embodiment includes: a residual amount after heating at 60 ℃ for 30 minutes is 95.0% or more of a monofunctional monomer, (meth) acrylate resin, photopolymerization initiator, and plasticizer, and a residual amount after heating at 80 ℃ for 3 hours is 95.0% or more. Here, the (meth) acrylate includes both methacrylate and acrylate. A photocurable resin composition is preferably used as the 1 st resin composition 6 and the 2 nd resin composition 8.
[ monofunctional monomer ]
The heating residual amount of the monofunctional monomer after heating at 60 ℃ for 30 minutes is preferably 95.0% or more, more preferably 97.0% or more, still more preferably 98.0% or more, and particularly preferably 99.50% or more.
Here, the residual amount of the monofunctional monomer upon heating is a value obtained by measuring the mass of 10mg of the monofunctional monomer before and after heating at 60 ℃ for 30 minutes using a calorimeter measurement apparatus (apparatus name: Q50, manufactured by TA Instruments).
When the photocurable resin composition contains the monofunctional monomer, volatilization of the monofunctional monomer can be more effectively suppressed when the 2 nd resin composition is heated in the step (C). Therefore, the adhesiveness between the light-transmissive member 3 and the image display member 2 can be further improved.
Specifically, the monofunctional monomer is preferably a monofunctional (meth) acrylate, and is preferably at least 1 of the compound represented by the formula (a) and the compound represented by the formula (B), for example.
[ chemical formula 1]
In the formula (A), R1Represents a hydrogen atom or a methyl group. R2Represents an alkylene group having 2 or 3 carbon atoms. R3The term "hydrocarbyl" refers to both aliphatic and aromatic hydrocarbyl groups. At R3When the alkyl group is an aliphatic hydrocarbon group, the alkyl group preferably has 5 to 10 carbon atoms. In addition, in R3When the aromatic hydrocarbon group is used, the aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably has 6 to 8 carbon atomsAnd (4) a base. In addition, in R3In the case of aromatic hydrocarbon radicals, R3May have a substituent. Examples of the substituent include a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, and the like. n represents an integer of 1 to 15, preferably an integer of 1 to 10.
In the formula (B), R4Represents a hydrogen atom or a methyl group. R5The number of carbon atoms of (A) is 11 to 20, preferably 15 to 20. R5The alkyl group may be any of a linear, branched or cyclic alkyl group, preferably a linear or branched alkyl group, and more preferably a branched alkyl group.
Specific examples of the monofunctional monomer include isostearyl (meth) acrylate, nonylphenol EO-modified (meth) acrylate, nonylphenol PO-modified (meth) acrylate, EO-modified 2-ethylhexyl (meth) acrylate, phenol EO-modified (meth) acrylate, o-phenylphenol EO-modified acrylate, p-cumylphenol EO-modified acrylate, N-acryloyloxyethylhexahydrophthalimide, 2-hydroxy-3-phenoxypropyl acrylate, and the like.
The content of the monofunctional monomer in the photocurable resin composition is preferably 5 to 60 mass%, more preferably 5 to 40 mass%, and still more preferably 10 to 30 mass%. The monofunctional monomer may be used alone in 1 kind, or may be used in combination in 2 or more kinds. In the case of using 2 or more kinds of monofunctional monomers in combination, the content thereof preferably satisfies the above content range.
[ (meth) acrylate resin ]
The (meth) acrylate resin is, for example, a photocurable (meth) acrylate resin, and may be a polymer or an oligomer. The (meth) acrylate resin is preferably at least 1 kind of a urethane (meth) acrylate oligomer, a polyisoprene (meth) acrylate oligomer, a polybutadiene (meth) acrylate oligomer, and a polyether (meth) acrylate oligomer, for example. Specific examples of the (meth) acrylate resin include UC-203 (manufactured by KURARAY Co., Ltd.), UV3700B (manufactured by Nippon synthetic chemical Co., Ltd.).
The content of the (meth) acrylate resin in the photocurable resin composition is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, even more preferably 10 to 60% by mass, and particularly preferably 30 to 50% by mass. The (meth) acrylate resin may be used alone in 1 kind, or 2 or more kinds may be used in combination. When 2 or more (meth) acrylate resins are used in combination, the content preferably satisfies the above content range.
[ photopolymerization initiator ]
The photopolymerization initiator is preferably a photo radical polymerization initiator, and more preferably contains at least 1 of an alkylphenone-based photopolymerization initiator and an acylphosphine oxide-based photopolymerization initiator. As the alkylphenone-based photopolymerization initiator, 1-hydroxycyclohexyl phenyl ketone (Irgacure 184, manufactured by BASF Co., Ltd.), 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) benzyl ] phenyl } -2-methyl-1-propan-1-one (Irgacure 127, manufactured by BASF Co., Ltd.) and the like can be used. As the acylphosphine oxide-based photopolymerization initiator, 2,4, 6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO, manufactured by BASF) or the like can be used. Furthermore, benzophenone, acetophenone, or the like can be used as a photopolymerization initiator.
In the photocurable resin composition, the content of the photopolymerization initiator is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, based on 100 parts by mass of the total of the monofunctional monomer and the (meth) acrylate resin. By setting the range as described above, the occurrence of insufficient curing at the time of light irradiation can be more effectively prevented, and the increase in outgas due to cracking can be more effectively prevented. The photopolymerization initiator may be used alone in 1 kind, or 2 or more kinds may be used in combination. When 2 or more kinds of photopolymerization initiators are used in combination, the total amount thereof preferably satisfies the above range.
[ plasticizer ]
The plasticizer is a substance which does not undergo photocuring by light irradiation, but imparts flexibility to a cured resin layer after photocuring. For example, polyisoprene plasticizers, polyether plasticizers, polybutadiene plasticizers, phthalate plasticizers, adipate plasticizers, and the like can be used. Specific examples of the polyisoprene-based plasticizer include LIR-30, LIR-50 (manufactured by KURARAAY Co., Ltd.), EPOL (manufactured by KANGISHENKO CO., Ltd.), and the like. Specific examples of the polyether plasticizer include P-3000 (manufactured by ADEKA). Specific examples of the polybutadiene-based plasticizer include HLBH-P2000, HLBH-P3000, LBH-P2000, LBHP3000, LBH-P5000 (as described above, manufactured by Cray Valley Co., Ltd.).
The content of the plasticizer in the photocurable resin composition is preferably 5 to 70% by mass, more preferably 10 to 70% by mass, and still more preferably 15 to 50% by mass. The plasticizer may be used alone in 1 kind, or may be used in combination of 2 or more kinds. When 2 or more kinds of plasticizers are used in combination, the total amount thereof preferably satisfies the above range.
[ other Components ]
The photocurable resin composition may further contain other components than the above-described components within a range not to impair the effects of the present technology. Examples thereof include inorganic fine particles and thickening agents.
The photocurable resin composition may contain inorganic fine particles in order to adjust the refractive index of at least one of the 1 st resin composition 6 and the 2 nd resin composition 8. As the inorganic fine particles, for example, silica particles whose surfaces are modified with alkylsilyl groups can be used. As the alkylsilyl group, a monoalkylsilyl group, a dialkylsilyl group or a trialkylsilyl group can be used. Examples of the shape of the inorganic fine particles include spherical, elliptical, flat, rod-like, and fibrous shapes. The average particle diameter of the inorganic fine particles is preferably, for example, 1 to 1000nm in consideration of dispersibility in the photocurable resin composition. The inorganic fine particles have a specific surface area (BET adsorption method) of, for example, 50 to 400m2And about/g.
The tackifier imparts flexibility to the cured resin layer formed from the photocurable resin composition, and further improves the initial adhesion strength (so-called tack) of the cured resin layer. Examples of the tackifier include terpene resins such as terpene resins, terpene phenol resins, and hydrogenated terpene resins, rosin resins such as natural rosin, polymerized rosin, rosin ester, and hydrogenated rosin, and petroleum resins such as polybutadiene and polyisoprene.
The light-curable resin composition preferably has a transmittance of more than 90%. This makes it possible to improve the visibility of the image formed on the image display member 2 when the cured resin layer 1 is formed.
The refractive index of the photocurable resin composition is preferably substantially equal to the refractive index of the image display member 2 or the light-transmitting member 3, and is preferably 1.45 or more and 1.55 or less, for example. This improves the brightness and contrast of the image light from the image display unit 2, thereby improving visibility.
The photocurable resin composition can be prepared by uniformly mixing the above components according to a known mixing method.
Examples
Examples of the present technology are explained below.
[ (meth) acrylate resin ]
UC-203: isoprene oligomer, manufactured by KURARAAY corporation
UV 3700B: urethane acrylate oligomer, manufactured by Nippon synthetic chemical Co.
[ monofunctional monomer ]
And (3) ISTA: isostearyl acrylate, manufactured by Osaka organic chemical industries, Ltd
M-111: nonylphenol EO-modified acrylate manufactured by Toyo Synthesis Ltd
M-113: nonylphenol EO-modified acrylate manufactured by Toyo Synthesis Ltd
M-117: nonylphenol PO-modified acrylate available from Toyo Synthesis Ltd
M-120: EO-MODIFIED 2-ETHYL ACRYLATE PRODUCED BY TOYOBA SYNTHESIS CO
M-101A: phenol EO-modified acrylate manufactured by Toyata Ltd
M-102: phenol EO-modified acrylate manufactured by Toyata Ltd
M-106: o-phenylphenol EO-modified acrylate manufactured by Toyo Synthesis Ltd
M-110: p-cumylphenol EO-modified acrylate manufactured by Toyata Ltd
M-140: N-Acryloxyethylhexahydrophthalimide manufactured by Toyata Synthesis Ltd
M-5700: acrylic acid 2-hydroxy-3-phenoxypropyl ester, manufactured by Toyama Synthesis Ltd
IBXA: isobornyl acrylate, manufactured by Osaka organic chemical industries, Ltd
HPA: hydroxypropyl acrylate, manufactured by Osaka organic chemical industries, Inc
[ plasticizer ]
LIR-30: isoprene Polymer, manufactured by KURARAAY corporation
P-3000: polyether polyol, manufactured by ADEKA Inc
[ polymerization initiator ]
Irg 184: 1-Hydroxycyclohexylphenylketone, manufactured by BASF
[ residual amount of monofunctional monomer upon heating ]
The residual heating amount (%) of each monofunctional monomer was determined by using a calorimeter (apparatus name: Q50, manufactured by TA Instruments). Specifically, as shown in FIG. 8, 10mg of the monofunctional monomer 13 was placed in the container 12, and the mass of the monofunctional monomer 13 was measured before and after heating at 60 ℃ for 30 minutes.
[ preparation of Photocurable resin composition ]
The respective components were uniformly mixed at the blending amounts (parts by mass) shown in table 1 to prepare a photocurable resin composition.
[ viscosity of Photocurable resin composition ]
The viscosity of the photocurable resin composition at 25 ℃ or 80 ℃ was measured by a rheometer (RS600, manufactured by HAAKE, Inc., cone angle C35/2 ℃).
[ refractive index of Photocurable resin composition ]
The refractive index after heating each photocurable resin composition at 80 ℃ for 3 hours and the refractive index before heating were measured using an Abbe refractometer (sodium D line (585nm), 25 ℃).
[ residual heating amount of photocurable resin composition ]
The residual heating amount (%) of each photocurable resin composition was determined using a calorimeter (device name: Q50, manufactured by TA Instruments). Specifically, as shown in fig. 9, 10mg of the photocurable resin composition 15 was placed in the container 14, and the mass of the photocurable resin composition 15 was measured before and after heating at 80 ℃ for 3 hours.
[ adhesive Strength without heating the Photocurable resin composition ]
As shown in FIGS. 10 and 11, a photocurable resin composition was dropped onto the center of a 1.1mm thick glass plate 16, and the 1.1mm thick glass plate 17 was placed so as to perpendicularly intersect with a 0.15mm spacer 19. Thus, a glass bonded body 20 having a resin composition layer 18 of 6mm in diameter and 0.15mm in thickness formed between the glass plates 16 and 17 was obtained.
As shown in FIGS. 12 and 13, the ultraviolet irradiator 9 was used so that the cumulative light amount became 5000mJ/cm2In the embodiment (1), the resin composition layer 18 is cured by irradiating the glass plate 17 with ultraviolet rays 10 to obtain a cured resin layer 21.
As shown in fig. 14, the glass plates 16 and 17 of the glass joined body 20 were fixed by jigs 22A and 22B, and pressed in at a speed of 5 mm/min in the vertical direction from the jig 22B side, and the adhesion state was evaluated according to the following criteria. A load tester (JSV-1000, Japan Instrument System Co., Ltd.) was used for measuring the adhesive strength. The adhesion strength was calculated by measuring the stress required until the glass plates 16 and 17 were separated at 25 ℃ and dividing the stress by the unit area of the cured resin layer 21.
[ adhesive Strength when Photocurable resin composition was heated ]
The measurement of the adhesive strength was carried out in the same manner as in the case where the photocurable resin composition was not heated, except that the composition heated at 80 ℃ for 3 hours was used as the photocurable resin composition dropped on the glass plate 16.
[ transmittance ]
The transmittance of the cured resin layer 21 in the glass joined body 20 in the visible light region was measured using an ultraviolet-visible spectrophotometer (UV-2450, manufactured by Shimadzu corporation). In practice, the transmittance of the cured resin layer 21 is preferably 90% or more.
[ Table 1]
The viscosity of the photocurable resin compositions of the examples was reduced by heating. Therefore, in the dam filling method, even when resin compositions having the same composition are used as the dam material (the 1 st resin composition) and the filler (the 2 nd resin composition), the high viscosity of the dam material and the low viscosity of the filler can be compatible with each other.
The photocurable resin compositions of the examples contained a monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes, and a residual heating amount of 95.0% or more after heating at 80 ℃ for 3 hours. Therefore, it was found that the adhesive strength was good even when the curable resin composition was heated in advance. Thus, for example, in the dam filling method, when the filler is heated, volatilization of components in the filler can be suppressed, and the adhesion between the members can be improved.
On the other hand, in comparative examples 1 and 2 using a resin composition having a residual heating amount after heating at 80 ℃ for 3 hours of less than 95.0%, it was found that the adhesive strength was not good when the resin composition was heated in advance. Therefore, for example, in the dam filling method, when the filler is heated, volatilization of components in the filler cannot be suppressed, and it is difficult to improve adhesion between the members. In comparative examples 3 and 4, it is clear that the adhesive strength is poor because a resin composition containing no monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes is used as the resin composition.
Description of the symbols
1 cured resin layer, 2 image display member, 3 light transmitting member, 4 light shielding layer, 5 image display device, 61 st resin composition, 7 2 nd resin composition coating region, 8 nd 2 nd resin composition, 9 ultraviolet irradiator, 10 ultraviolet, 11 liquid stopping part (cofferdam), 12 container, 13 monofunctional monomer, 14 container, 15 photocurable resin composition, 16 glass plate, 17 glass plate, 18 resin composition layer, 19 gasket, 20 glass conjugant, 21 cured resin layer, 22A, 22B clamp.
Claims (14)
1. A method of making a laminate, the method having:
a step A of forming a coating region of a 2 nd photocurable resin composition on the surface of the 1 st member using the 1 st resin composition,
a step B of applying the 2 nd resin composition to the application region,
a step C of bonding the 1 st member and the 2 nd member via the 2 nd resin composition to fill the coating region with the 2 nd resin composition, and
a step D of forming a cured resin layer by irradiating the 2 nd resin composition with light; wherein,
the step C comprises heating the 2 nd resin composition,
the 2 nd resin composition contains a monofunctional monomer having a residual heating amount of 95.0% or more after heating at 60 ℃ for 30 minutes,
the residual heating amount of the above-mentioned 2 nd resin composition after heating at 80 ℃ for 3 hours is 95.0% or more.
2. The method of producing a laminate according to claim 1, wherein in the step C, the 2 nd resin composition is filled in the coating region in a visbroken state by the heating.
3. The laminate production method according to claim 1, wherein the 2 nd resin composition further contains a (meth) acrylate resin, a photopolymerization initiator and a plasticizer.
4. The laminate production method according to claim 1, wherein the monofunctional monomer is at least 1 of a compound represented by formula (a) and a compound represented by formula (B):
[ chemical formula 1]
In the formula (A), R1Represents a hydrogen atom or a methyl group, R2Represents an alkylene group having 2 or 3 carbon atoms, R3Represents a hydrocarbon group, n represents an integer of 1 to 15; in the formula (B), R4Represents a hydrogen atom or a methyl group, R5Represents an alkyl group having 11 to 20 carbon atoms.
5. The method of producing a laminate according to claim 1, wherein the monofunctional monomer is at least 1 selected from the group consisting of isostearyl (meth) acrylate, nonylphenol EO-modified (meth) acrylate, nonylphenol PO-modified (meth) acrylate, EO-modified 2-ethylhexyl (meth) acrylate, phenol EO-modified (meth) acrylate, orthophenylphenol EO-modified acrylate, p-cumylphenol EO-modified acrylate, N-acryloyloxyethylhexahydrophthalimide, and 2-hydroxy-3-phenoxypropyl acrylate.
6. The method for producing a laminate according to claim 1, wherein the monofunctional monomer is contained in an amount of 5 to 60% by mass in the 2 nd resin composition.
7. The method of manufacturing a laminate according to claim 3, wherein,
in the above-mentioned resin composition of the 2 nd aspect,
the content of the monofunctional monomer is 5 to 60% by mass,
the content of the (meth) acrylate resin is 10 to 60% by mass,
the content of the plasticizer is 10 to 70% by mass.
8. The method of producing a laminate according to claim 1, wherein in the step C, the 2 nd resin composition is heated at 60 to 80 ℃.
9. The method of producing a laminate according to claim 1, wherein the residual heating amount of the 2 nd resin composition is 97.0% or more.
10. The method of manufacturing a laminate according to claim 1,
in the step B, the 2 nd resin composition having a viscosity of 10000 to 50000 mPas at 25 ℃ is applied,
in the step C, the coated region is filled with the heated second resin composition in a state where the viscosity of the second resin composition is 3000mPa · s or less.
11. The method of manufacturing a laminate according to claim 1, wherein the step B comprises heating the 2 nd resin composition.
12. The method of producing a laminate according to claim 1, wherein at least one of the 1 st resin composition and the 2 nd resin composition contains inorganic fine particles.
13. The method of producing a laminate according to claim 1, wherein the 1 st resin composition and the 2 nd resin composition are the same component.
14. The method for producing a laminate according to any one of claims 1 to 13, wherein,
the 1 st member or the 2 nd member is an image display member,
the laminate is an image display device.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110418562.8A CN113372823B (en) | 2017-02-28 | 2018-01-12 | Method for producing laminate and photocurable resin composition |
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| JP2017-037614 | 2017-02-28 | ||
| JP2017037614A JP6938168B2 (en) | 2017-02-28 | 2017-02-28 | Method for producing a laminate and a photocurable resin composition |
| PCT/JP2018/000578 WO2018159110A1 (en) | 2017-02-28 | 2018-01-12 | Manufacturing method for laminated body, and photocurable resin composition |
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| CN202110418562.8A Division CN113372823B (en) | 2017-02-28 | 2018-01-12 | Method for producing laminate and photocurable resin composition |
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| JP (3) | JP6938168B2 (en) |
| KR (3) | KR102318425B1 (en) |
| CN (2) | CN113372823B (en) |
| DE (1) | DE112018001039T5 (en) |
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| JP7274966B2 (en) | 2019-07-29 | 2023-05-17 | デクセリアルズ株式会社 | Optical device manufacturing method |
| WO2023026956A1 (en) * | 2021-08-26 | 2023-03-02 | デクセリアルズ株式会社 | Photocurable material and image display device |
| KR20230093749A (en) * | 2021-12-20 | 2023-06-27 | 주식회사 동진쎄미켐 | Adhesive composition with excellent adhesion and reliability |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR102692688B1 (en) | 2024-08-08 |
| KR20210130272A (en) | 2021-10-29 |
| CN110234506A (en) | 2019-09-13 |
| JP6938168B2 (en) | 2021-09-22 |
| DE112018001039T5 (en) | 2019-11-28 |
| JP2022000508A (en) | 2022-01-04 |
| KR102318425B1 (en) | 2021-10-28 |
| JP2018140601A (en) | 2018-09-13 |
| KR20190072606A (en) | 2019-06-25 |
| CN113372823A (en) | 2021-09-10 |
| WO2018159110A1 (en) | 2018-09-07 |
| KR20240034266A (en) | 2024-03-13 |
| JP2023086991A (en) | 2023-06-22 |
| TW201834848A (en) | 2018-10-01 |
| CN113372823B (en) | 2023-05-26 |
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