WO2022054912A1 - 樹脂組成物、硬化物及びその製造方法、並びに積層体 - Google Patents
樹脂組成物、硬化物及びその製造方法、並びに積層体 Download PDFInfo
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- WO2022054912A1 WO2022054912A1 PCT/JP2021/033338 JP2021033338W WO2022054912A1 WO 2022054912 A1 WO2022054912 A1 WO 2022054912A1 JP 2021033338 W JP2021033338 W JP 2021033338W WO 2022054912 A1 WO2022054912 A1 WO 2022054912A1
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- URQKFYSBGUPSDD-UHFFFAOYSA-N phenyl(propylsilyl)methanol Chemical class C(CC)[SiH2]C(C1=CC=CC=C1)O URQKFYSBGUPSDD-UHFFFAOYSA-N 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- MIMYMWKOIOSJOA-UHFFFAOYSA-N phenyl-dipropoxy-propylsilane Chemical compound CCCO[Si](CCC)(OCCC)C1=CC=CC=C1 MIMYMWKOIOSJOA-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- KCTGOQZIKPDZNK-UHFFFAOYSA-N tetrapentyl silicate Chemical compound CCCCCO[Si](OCCCCC)(OCCCCC)OCCCCC KCTGOQZIKPDZNK-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- HSDAZXVGQVMFAY-UHFFFAOYSA-N tributyl methyl silicate Chemical compound CCCCO[Si](OC)(OCCCC)OCCCC HSDAZXVGQVMFAY-UHFFFAOYSA-N 0.000 description 1
- PZOOLKGCOFWELU-UHFFFAOYSA-N tributyl propyl silicate Chemical compound CCCCO[Si](OCCC)(OCCCC)OCCCC PZOOLKGCOFWELU-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- CXZMPNCYSOLUEK-UHFFFAOYSA-N triethyl propyl silicate Chemical compound CCCO[Si](OCC)(OCC)OCC CXZMPNCYSOLUEK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WKEXHTMMGBYMTA-UHFFFAOYSA-N trimethyl propyl silicate Chemical compound CCCO[Si](OC)(OC)OC WKEXHTMMGBYMTA-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- PSFMLZCIUDXLPX-UHFFFAOYSA-N tripentoxy(phenyl)silane Chemical compound CCCCCO[Si](OCCCCC)(OCCCCC)C1=CC=CC=C1 PSFMLZCIUDXLPX-UHFFFAOYSA-N 0.000 description 1
- OMBAQAOBNOSBNU-UHFFFAOYSA-N tripentoxy(propyl)silane Chemical compound CCCCCO[Si](CCC)(OCCCCC)OCCCCC OMBAQAOBNOSBNU-UHFFFAOYSA-N 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- C08F290/068—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- 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
- B05D2203/00—Other substrates
- B05D2203/30—Other inorganic substrates, e.g. ceramics, silicon
- B05D2203/35—Glass
-
- 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
- B05D2518/00—Other type of polymers
- B05D2518/10—Silicon-containing polymers
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
Definitions
- the present invention relates to a resin composition, a cured product and a method for producing the same, and a laminate.
- This application is based on Japanese Patent Application No. 2020-15163 filed in Japan on September 11, 2020, and Japanese Patent Application Nos. 2020-198572 and 2020-199028 filed in Japan on November 30, 2020. And the priority is claimed based on Japanese Patent Application No. 2020-199037, and the contents thereof are incorporated herein by reference.
- Polymethylmethacrylate resin, polymethacrylicimide resin, polycarbonate resin, polystyrene resin, acrylonitrile styrene resin and the like are used for members such as various lamp lenses for automobiles, glazing, exteriors, and covers of instruments. Resin molded products made from these resins are lightweight, have excellent impact resistance, and have good transparency. Further, in recent years, with the miniaturization of various parts, transparent glass having excellent durability has been increasingly used for the cover member.
- ADAS advanced driver assistance system
- a sensor device sometimes called a millimeter-wave radar
- radio waves millimeter waves
- LiDAR sensor device
- Patent Document 1 describes a silicone composition containing a tetrafunctional alkoxysilane and a trifunctional alkoxysilane or a partially hydrolyzed condensate thereof, a reactive silicone having a specific structure containing a polydimethylsiloxane structure, an acid or a base catalyst, and the like. Coating compositions containing water have been proposed.
- the coating composition described in Patent Document 1 has a high curing temperature, so that it is not suitable for a resin base material, for example.
- the compatibility between the component contributing to water permeability and other components is poor, and the appearance of the formed coating layer is easily spoiled.
- the durability of the coating layer is insufficient, and the appearance and water-sliding property may be deteriorated by the moisture resistance test.
- the present invention relates to a resin composition capable of forming a cured product having excellent appearance, water-sliding and durability, a cured product having excellent appearance, water-sliding, weather resistance and durability and a method for producing the same, and appearance, water-sliding and weather resistance. It is an object of the present invention to provide a laminate having a cured product layer having excellent durability.
- the total of the ratio of the structural unit based on the silicone macromonomer (X) and the ratio of the structural unit based on the monomer (Y) to the total mass of all the structural units constituting the copolymer (A) is 55.
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R3 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- m represents an integer of 3 to 4 according to M
- r represents an integer of 0 to 3
- r R 2s may be different from each other
- mr is In the case of 2 or more, the (mr) OR 3s may be different from each other.
- R 4 represents a hydrogen atom, an alkyl group, an aryl group or an aralkyl group
- R 5 represents an alkyl group or a phenyl group
- n represents an integer of 2 to 4
- n OR 5s are different from each other.
- n represents an integer of 2 to 4
- n represents an integer of 2 to 4
- n OR 5s are different from each other.
- n represents an integer of 2 to 4
- R4s may be different from each other.
- the proportion of the structural unit based on the silicone macromonomer (X) is 15 to 60% by mass with respect to the total mass of all the structural units constituting the copolymer (A), and the monomer (Y).
- a partially hydrolyzed condensate in which the component (B) is at least one kind of the silane compound and has a weight average molecular weight of 300 to 3000 is further hydrolyzed in the presence of a catalyst.
- a component (B) composed of a silane compound or a partially hydrolyzed condensate thereof.
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R3 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- m represents an integer of 3 to 4 according to M
- r represents an integer of 0 to 3
- r R 2s may be different from each other
- mr is In the case of 2 or more, the (mr) OR 3s may be different from each other.
- a resin composition comprising, a component (B) composed of a silane compound or a partial hydrolysis condensate thereof, and a photopolymerization initiator. -R 1 -M (R 2 ) r (OR 3 ) m-r ...
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R3 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R3 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- a method for producing a cured product wherein a resin composition containing a silane compound or a component (B) containing a partially hydrolyzed condensate thereof is cured by heat treatment or irradiation with active energy rays.
- a resin composition containing a silane compound or a component (B) containing a partially hydrolyzed condensate thereof is cured by heat treatment or irradiation with active energy rays.
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R3 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- m represents an integer of 3 to 4 according to M
- r represents an integer of 0 to 3
- r R 2s may be different from each other
- mr is In the case of 2 or more, the (mr) OR 3s may be different from each other.
- a resin composition capable of forming a cured product having excellent curability and excellent appearance, water-sliding, weathering resistance and durability, a cured product having excellent appearance, water-sliding, weathering resistance and durability, and a method for producing the same.
- a laminate having a cured product layer excellent in appearance, water slipperiness, weather resistance and durability can be provided.
- the resin composition according to one aspect of the present invention is a copolymer (A) containing a polydimethylsiloxane unit and at least one specific silane compound or a portion thereof. It contains a component (B) composed of a hydrolysis condensate.
- the present resin composition may further contain an initiator (C) and a diluent, if necessary.
- the present resin composition may further contain components other than the above, if necessary.
- the copolymer (A) contains a polyalkylsiloxane unit.
- the polyalkylsiloxane unit contains two or more alkylsiloxane units. Examples of the polyalkylsiloxane unit include a linear type, a branched type, and a dendrimer type, and among them, a linear type polyalkylsiloxane unit represented by- ( Si (R18) 2O ) n- may be contained. preferable.
- R 18 represents a hydrocarbon group having 1 to 10 carbon atoms, preferably a hydrocarbon group having 1 to 5 carbon atoms, and more preferably a methyl group.
- n indicates the average degree of polymerization of the polyalkylsiloxane unit.
- the average degree of polymerization of the polyalkylsiloxane unit is preferably 5 to 1000, more preferably 10 to 500, still more preferably 30 to 300, and particularly preferably 50 to 200.
- the average degree of polymerization is at least the above lower limit value, the water-sliding property of the cured product of the present resin composition is more excellent, and when it is at least the above upper limit value, a monomer having a polyalkylsiloxane unit (a silicone macromonomer described later).
- X)) is easily compatible with other monomers, and the copolymer (A) tends to be easily produced.
- the copolymer (A) may contain a polyalkylsiloxane unit in the main chain, in the side chain, or in both the main chain and the side chain. From the viewpoint of water permeability and ease of production of the copolymer (A), it is preferable to include a polydimethylsiloxane unit in at least the side chain.
- the copolymer (A) containing at least the polyalkylsiloxane unit in the side chain is used in consideration of the ease of introducing the polyalkylsiloxane unit and the ease of controlling the performance such as slipperiness.
- a copolymer containing a structural unit based on the silicone macromonomer (X) hereinafter, also referred to as “macromonomer (X)”) (hereinafter, also referred to as “constituent unit (X)”) is preferable.
- the copolymer (A) is a structural unit based on the monomer (Y) having a group represented by the specific formula (1) from the viewpoint of improving the performance such as water-sliding property (hereinafter, “constituent unit (hereinafter,“ structural unit (hereinafter, “constituent unit”). It is also preferable to further include Y) ”.
- the copolymer (A) is a structural unit based on a monomer (Z) other than the macromonomer (X) and the monomer (Y), if necessary, as long as the performance is not impaired (hereinafter, “constituent unit”). (Z) ”) may be further included.
- silicone macromonomer (X) examples include compounds containing a polyalkylsiloxane unit and a polymerizable functional group.
- the polymerizable functional group may be any group containing a polymerizable unsaturated bond such as a polymerizable carbon-carbon double bond, and examples thereof include a (meth) acryloyl group, a vinyl group, and a (meth) acrylamide group. .. Among these, the (meth) acryloyl group is preferable from the viewpoint of easiness of copolymerization with other monomers.
- the polyalkylsiloxane unit and the polymerizable functional group may be bonded via a linking group. Examples of the linking group include a hydrocarbon group such as an alkylene group having 1 to 6 carbon atoms.
- silicone macromonomer (X) having a (meth) acryloyl group examples include a compound represented by the following formula (2).
- CH 2 CR 19 -CO-O-R 20- (Si (R 18 ) 2 O) n -R 21 ...
- R 18 represents a hydrocarbon group having 1 to 10 carbon atoms
- n represents an average degree of polymerization
- R 19 represents a hydrogen atom or a methyl group
- R 20 represents a hydrocarbon group having 1 to 10 carbon atoms.
- R 21 represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or an aryl group.
- n is the same as the preferable range of the average degree of polymerization of the polyalkylsiloxane unit described above.
- R 18 represents a hydrocarbon group having 1 to 10 carbon atoms, a hydrocarbon group having 1 to 5 carbon atoms is preferable, a methyl group is more preferable, R 19 is preferably a methyl group, and R 20 is carbon.
- a hydrocarbon group having 1 to 6 carbon atoms is preferable, a hydrocarbon group having 2 to 4 carbon atoms is more preferable, a hydrocarbon group having 1 to 6 carbon atoms is preferable, and a hydrocarbon group having 1 to 4 carbon atoms is more preferable. preferable.
- the weight average molecular weight of the silicone macromonomer (X) (hereinafter, also referred to as “Mw”) is preferably 500 to 40,000, more preferably 700 to 30,000, further preferably 800 to 20,000, particularly preferably 1,000 to 18,000, and 2000. ⁇ 15000 is the most preferable.
- Mw of the silicone macromonomer (X) is at least the above lower limit value, the smoothness of the cured product of the present resin composition is more excellent, and when it is at least the above upper limit value, the silicone macromonomer (X) is a monomer ( It tends to be easily compatible with Y) and the monomer (Z), and it tends to be easy to produce the copolymer (A).
- Mw of the silicone macromonomer (X) is a standard polystyrene-equivalent value measured by gel permeation chromatography (GPC).
- silicone macromonomer (X) a commercially available product can be used.
- linear silicone macromonomers (X) include JNC's Cyraplane (registered trademark) FM-0711 (number average molecular weight catalog publication value: 1000) and Cyraplane FM-0721 (number average).
- Silaplane FM-0725 number average molecular weight catalog publication value: 10000
- X-22-174ASX number average molecular weight catalog publication value: 900
- -174BX number average molecular weight catalog publication value: 2300
- KF-2012 number average molecular weight catalog publication value: 4600
- X-22-2426 number average molecular weight catalog publication value: 12000
- examples of the dendrimer type silicone macromonomer (X) include HGO-3002 manufactured by Silicon Material Development. As the silicone macromonomer (X), one type may be used alone, or two or more types may be used in combination.
- the monomer (Y) has a group represented by the following formula (1) (hereinafter, also referred to as “group (1)”).
- group (1) When the group (1) is introduced into the copolymer (A) by the monomer (Y), the group (1) in the copolymer (A) and the component (B) react with each other to form a polydimethylsiloxane unit. Can be prevented from bleeding out to the surface of the cured product of the present resin composition, and the durability is improved.
- M represents Al, Fe, In, Ge, Hf, Si, Ti, Sn, Zr, or Ta
- R 1 represents a hydrocarbon group having 1 to 5 carbon atoms
- R 2 represents a hydrocarbon group having 1 to 5 carbon atoms.
- R 3 represents a hydrogen atom , an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an aryl group, or an acyl group.
- M represents an integer of 3 to 4 according to M
- r represents an integer of 0 to 3
- r R2s may be different from each other
- mr is 2.
- the (mr) R3s may be different from each other.
- M is Al (aluminum), Fe (iron), In (indium), Ge (germanium), Hf (hafnium), Si (silicon), Ti (titanium), Sn (tin), Either Zr (zirconium) or Ta (tantal) may be used, but Al, Si, Ti, or Zr is preferable from the viewpoint of reactivity and availability, and Si is particularly preferable because it is inexpensive and easy to use. ..
- Examples of the aryl group of R 2 and R 3 include a phenyl group, a toluyl group, a naphthyl group and the like.
- the alkyl group, alkenyl group, and aryl group of R 2 and R 3 may each have a substituent.
- Examples of the substituent include a halogen atom such as a chlorine atom, a methoxy group, an alkoxy group of an ethoxy group, and the like.
- acyl group of R 3 examples include a (meth) acrylic group, an acetyl group, an acetimideyl group, an aldehyde group, a thioacetyl group, a propionyl group, a benzenesulfonyl group and a benzoyl group.
- OR 3 can be subdivided into an alkoxy group, an alkenyloxy group, an aryloxy group, an acyloxy group, a ketoximate group, and a hydroxy group.
- an alkoxy group, an alkenyloxy group, an acyloxy group, and a hydroxy group are preferable because of their high reactivity, and an alkoxy group such as a methoxy group and an ethoxy group or a hydroxy group is preferable because the hydrolyzability is easy to control and handle. Groups are particularly preferred.
- Examples of the group (1) (also referred to as a hydrolyzable silyl group) when M in the formula (1) is Si include a trimethoxysilyl group, a triethoxysilyl group, a triisopropoxysilyl group and a dimethoxymethylsilyl.
- Group, diethoxymethylsilyl group, diisopropoxymethylsilyl group, tris (2-propenyloxy) silyl group, (chloromethyl) dimethoxysilyl group, (methoxymethyl) dimethoxysilyl group, (methoxymethyl) diethoxysilyl group, (Ethoxymethyl) dimethoxysilyl group is mentioned.
- a trimethoxysilyl group, a triethoxysilyl group, and a dimethoxymethylsilyl group are preferable, and a dimethoxymethylsilyl group is more preferable, from the viewpoint of general purpose, high activity, and good curability.
- a dimethoxymethylsilyl group and a triethoxysilyl group are preferable.
- a (chloromethyl) dimethoxysilyl group and a (methoxymethyl) dimethoxysilyl group are preferable from the viewpoint of exhibiting particularly high curability.
- a trifunctional silyl group such as a trimethoxysilyl group or a triethoxysilyl group is preferable in that the recoverability of the cured product tends to be high.
- Examples of the monomer (Y) include a compound having the above-mentioned group (1) and a polymerizable functional group or a reactive group capable of being added (polymer reaction) to the polymer.
- Examples of the polymerizable functional group include the same as described above, and the same applies to preferred embodiments.
- Examples of the reactive group include a vinyl group, a (meth) acryloyl group, a (meth) acrylamide group, an epoxy group, a cyclic epoxy group, a mercapto group, an amino group, a diamino group, an acid anhydride group, an isocyanate group and the like. ..
- the group (1) and the polymerizable functional group or the reactive group may be bonded via a linking group.
- Examples of the linking group include a hydrocarbon group such as an alkylene group having 1 to 6 carbon atoms.
- Examples of the monomer (Y) include vinyltrimethoxysilane, vinyltriethoxylan, vinyltris ( ⁇ -methoxyethoxy) silane, (meth) acrylic acid (3-trimethoxysilyl) propyl, and (meth) acrylic.
- Vinyl-based silane compounds such as acrylic acid (dimethoxymethylsilyl) methyl, ⁇ -aminopropyltrimethoxylane, N- ⁇ - (aminoethyl) ⁇ -aminopropyltrimethoxysilane, N- ⁇ - (aminoethyl) ⁇ - Amino-based silane compounds such as aminopropylmethyldimethoxysilane and ⁇ -ureidopropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxylane, ⁇
- the monomer (Y) is not limited to these.
- a titanate-based, aluminate-based, or zirconate-based coupling agent having a polymerizable functional group that can be copolymerized with another monomer or a reactive group other than the group (1) that can be added to the polymer may be used. good.
- the monomer (Y) one type may be used alone, or two or more types may be used in combination.
- the silicone macromonomer (X) and the monomer (Y) are copolymerized, the better the copolymerizability of the silicone macromonomer (X) and the monomer (Y), the more the unreacted monomer is reduced. This can be done, and the durability of the cured product of the present resin composition tends to be improved.
- the polymerizable functional group of the silicone macromonomer (X) is a (meth) acryloyl group
- the monomer (Y) is particularly preferably a vinyl-based silane compound having a (meth) acryloyl group.
- the monomer (Z) may be copolymerizable with the silicone macromonomer (X), and for example, the above-mentioned compound having a polymerizable functional group (however, the silicone macromonomer (X) and the monomer (Y)) may be used. ) Is excluded.)
- the monomer (Z) include the following. Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, (meth) acrylic Acid tert-butyl, (meth) acrylate n-pentyl, (meth) acrylate n-hexyl, (meth) acrylate cyclohexyl, (meth) acrylate n-heptyl, (meth) acrylate n-octyl, (meth) ) 2-ethylhexyl acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, phenyl (meth) acrylate, toluyl (
- Styrene-based monomers such as styrene, vinyltoluene, ⁇ -methylstyrene, chlorstyrene, styrenesulfonic acid and salts thereof.
- Maleic anhydride maleic acid, monoalkyl esters and dialkyl esters of maleic acid; monoalkyl esters and dialkyl esters of fumaric acid, fumaric acid.
- Maleimide-based monomers such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide, and cyclohexylmaleimide.
- Nitrile group-containing vinyl-based monomers such as acrylonitrile and methacrylonitrile.
- Amide group-containing vinyl-based monomers such as acrylamide and methacrylamide.
- Vinyl esters such as vinyl acetate, vinyl propionate, vinyl pivalate, vinyl benzoate, and vinyl cinnamic acid.
- Alkenes such as ethylene and propylene. Conjugated diene such as butadiene and isoprene. Vinyl chloride, vinylidene chloride, allyl chloride, allyl alcohol, etc.
- the monomer (Z) one type may be used alone, or two or more types may be used in combination.
- the silicone macromonomer (X) and the monomer (Z) are copolymerized, the better the copolymerizability of the silicone macromonomer (X) and the monomer (Z), the more the unreacted monomer is reduced. This can be done, and the durability of the cured product of the present resin composition tends to be improved.
- the polymerizable functional group of the silicone macromonomer (X) is a (meth) acryloyl group
- the monomer (Z) is derived from the styrene-based monomer and the (meth) acrylic acid-based monomer. At least one of them is preferable, and a (meth) acrylic acid-based monomer is particularly preferable.
- the ratio of the structural unit (X) to the total mass of all the structural units constituting the copolymer (A) is preferably 15 to 60% by mass, more preferably 15 to 50% by mass, still more preferably 20 to 50% by mass. ..
- the ratio of the structural unit (X) is at least the above lower limit value, the smoothness of the cured product becomes better, and when it is at least the above upper limit value, the amount of unpolymerized silicone macromonomer (X) can be reduced. Therefore, the transparency of the cured product tends to be good.
- the ratio of the structural unit (Y) to the total mass of all the structural units constituting the copolymer (A) is preferably 40 to 85% by mass, more preferably 40 to 80% by mass, still more preferably 40 to 75% by mass. ..
- the ratio of the constituent unit (Y) is at least the above lower limit value, the durability of the cured product is better, and when it is at least the above upper limit value, the proportion of the constituent unit (X) can be sufficiently increased, so that the cured product is cured.
- the water-sliding property of an object tends to be good.
- the total of the ratio of the structural unit based on the silicone macromonomer (X) and the ratio of the structural unit based on the monomer (Y) to the total mass of all the structural units constituting the copolymer (A) is 55% by mass.
- the above is preferable, 70% by mass or more is more preferable, 80% by mass or more is further preferable, 90% by mass or more is particularly preferable, and 100% by mass is most preferable.
- the total of the ratios of the structural unit (X) and the structural unit (Y) is at least the above lower limit value, the durability of the cured product and the water-sliding property of the cured product tend to be better.
- the ratio of the structural unit (Z) to the total mass of all the structural units constituting the copolymer (A) is preferably 0 to 45% by mass, more preferably 0 to 40% by mass, still more preferably 0 to 30% by mass. , 0 to 20% by mass is particularly preferable, and 0 to 10% by mass is most preferable.
- the higher the proportion of the structural unit (Z) the better the copolymerizability when producing the copolymer (A) tends to be.
- the ratio of each structural unit is obtained by an analysis method such as infrared spectroscopic analysis by a nuclear magnetic resonance method or a total internal reflection measurement method.
- the Mw of the copolymer (A) is preferably 3000 to 40000, more preferably 5000 to 100,000, and particularly preferably 7000 to 80000. Further, 8000 to 40,000 is more preferable.
- the Mw of the copolymer (A) is equal to or higher than the above lower limit value, the copolymer (A) is firmly immobilized in the cured product, so that the water smoothness and durability tend to be improved, and the above upper limit value. If the following, the compatibility with other components in the present resin composition is improved, so that the appearance of the cured product tends to be improved.
- the Mw of the copolymer (A) is a standard polystyrene-equivalent value measured by gel permeation chromatography (GPC).
- the method for producing the copolymer (A) is not particularly limited, and a known method can be appropriately adopted.
- a copolymer having a structural unit (X) and a structural unit (Y) can be produced by the following method (i) or (ii).
- a monomer mixture containing a silicone macromonomer (X) and, if necessary, a monomer (Z) is polymerized, and the obtained polymer contains a reactive group that can be added to the polymer.
- the ratio of the silicone macromonomer (X) to the total mass of the silicone macromonomer (X), the monomer (Y) and the monomer (Z) is 15 to 60% by mass. Is preferable, 15 to 50% by mass is more preferable, and 20 to 50% by mass is further preferable.
- the ratio of the silicone macromonomer (X) is not less than the above lower limit value, the smoothness of the cured product becomes better, and when it is not more than the above upper limit value, the amount of unpolymerized silicone macromonomer (X) can be reduced. As a result, the transparency of the cured product tends to be good.
- the ratio of the monomer (Y) to the total mass of the silicone macromonomer (X), the monomer (Y), and the monomer (Z) is preferably 40 to 85% by mass, more preferably 40 to 80% by mass. It is preferable, and more preferably 40 to 75% by mass.
- the proportion of the monomer (Y) is at least the above lower limit value, the durability of the cured product becomes better, and when it is at least the above upper limit value, the proportion of the silicone macromonomer (X) can be sufficiently increased. , The water-sliding property of the cured product tends to be good.
- the ratio of the monomer (Z) to the total mass of the silicone macromonomer (X), the monomer (Y), and the monomer (Z) is preferably 0 to 45% by mass, more preferably 0 to 40% by mass. It is preferable, 0 to 30% by mass is more preferable, 0 to 20% by mass is particularly preferable, and 0 to 10% by mass is most preferable.
- the higher the proportion of the monomer (Z) the better the copolymerizability of the monomer mixture tends to be.
- the polymerization method of the monomer mixture is not particularly limited, and known polymerization methods such as solution polymerization method, suspension polymerization, bulk polymerization and emulsion polymerization can be used.
- the polymerization conditions are not particularly limited, but can be, for example, 0.5 to 24 hours at 30 to 180 ° C.
- the monomer mixture is preferably polymerized in the presence of a polymerization initiator.
- a polymerization initiator various known polymerization initiators can be used.
- V-70 2,2-azobis (4-methoxy-2,4-dimethylvaleronitrile)
- V-65 2,2'-azobis (2,4-dimethylvaleronitrile)
- Nichiyu Nichiyu
- Succinic Acid Peroxide Paroyl SA, Nichiyu
- Benzoyl Peroxide Nyper® BW, Nichiyu
- Isobutylyl Peroxide Paroyl IB, Nichiyu
- 2 4-Dichlorobenzoyl peroxide (Nyper CS, manufactured by Nissui), 3,5,5-trimethylhexanoyl peroxide (Paroyl355, manufactured by Nissui), etc.
- Dialkyl peroxides such as 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane (Perhexa® 25B, manufactured by Nichiyu); ⁇ , ⁇ '-bis (manufactured by Nichiyu).
- Neodecanoylperoxy Diisopropylbenzene (Diper (registered trademark) ND, manufactured by Nichiyu), Kumilperoxy Neodecanoate (Parkmill (registered)) Trademarks) ND, manufactured by NOF Corporation), 1,1,3,3-tetramethylbutylperoxyneodecanoate (PeroctaND, manufactured by NOF CORPORATION), 1-cyclohexyl-1-methylethylperoxyneodecanoate (trademark) Percyclo (registered trademark) ND, manufactured by NOF Corporation, t-hexyl peroxyneodecanoate (Perhexyl (registered trademark) ND, manufactured by NOF Corporation), t-butyl peroxyneodecanoate (perbutyl ND, manufactured by NOF) ), T-hexyl peroxypivalate (Perhexyl PV, NOF), t-butyl peroxypivalate (Per
- the polymerization initiator is not particularly limited to these.
- the polymerization initiator one type may be used alone, or two or more types may be used in combination.
- the amount of the polymerization initiator used is, for example, 0.01 to 10 parts by mass with respect to 100 parts by mass of the monomer mixture.
- a silicone macromonomer (X) and a monomer (Z) containing a hydroxyl group are copolymerized, and then an isocyanate group is used.
- examples thereof include a method of addition-reacting a compound containing a compound (1) with a group (1), but the present invention is not particularly limited.
- the component (B) is composed of at least one silane compound represented by the following formula (b) (hereinafter, also referred to as “silane compound (b)”) or a partially hydrolyzed condensate thereof.
- silane compound (b) represented by the following formula (b) (hereinafter, also referred to as “silane compound (b)”) or a partially hydrolyzed condensate thereof.
- R 4 4-n Si (OR 5 ) n ...
- R 4 represents a hydrogen atom, an alkyl group, an aryl group or an aralkyl group
- R 5 represents an alkyl group or a phenyl group
- n represents an integer of 2 to 4
- n OR 5s are different from each other.
- n is 2, ( 4 -n) R4s may be different from each other.
- the alkyl group of R4 may be linear or branched.
- the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 4.
- the aryl group include a phenyl group, a toluyl group, a naphthyl group and the like.
- the aralkyl group include a benzyl group and a phenethyl group.
- the alkyl group of R5 may be linear or branched, and is preferably linear from the viewpoint of hydrolysis rate.
- the number of carbon atoms of the alkyl group is preferably 1 to 5, more preferably 1 or 2, and even more preferably 1 from the viewpoint of the rate of hydrolysis.
- silane compound (b1) The silane compound when n in the formula (b) is 4 (hereinafter, also referred to as “silane compound (b1)”) is represented by the following formula (b1).
- R 6 , R 7 , R 8 and R 9 independently represent an alkyl group or a phenyl group, respectively.
- R6, R7 , R8 and R9 are the same as R5 above.
- silane compound (b2) The silane compound when n in the formula (b) is 3 (hereinafter, also referred to as “silane compound (b2)”) is represented by the following formula (b2).
- R 10 represents a hydrogen atom, an alkyl group, an aryl group or an aralkyl group.
- R 11 , R 12 and R 13 independently represent an alkyl group or a phenyl group, respectively.
- R 10 is the same as R 4 above.
- R 11 , R 12 and R 13 are the same as R 5 above.
- silane compound (b3) The silane compound when n in the formula (b) is 2 (hereinafter, also referred to as “silane compound (b3)”) is represented by the following formula (b3).
- R 14 and R 15 independently represent a hydrogen atom, an alkyl group, an aryl group or an aralkyl group, respectively.
- R 16 and R 17 independently represent an alkyl group or a phenyl group, respectively.
- R 14 and R 15 are the same as R 4 above.
- R 16 and R 17 are the same as R 5 above.
- silane compound (b1) examples include tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetrabutoxysilane, tetrapentyloxysilane, tetraphenyloxysilane, trimethoxymonoethoxysilane, dimethoxydiethoxysilane, and triethoxy.
- silane compound (b2) examples include trimethoxysilane, triethoxysilane, tripropoxysilane, trypentyloxysilane, triphenyloxysilane, dimethoxymonoethoxysilane, diethoxymonomethoxysilane, and dipropoxymonomethoxysilane.
- Dipropoxymonoethoxysilane dipentyloxylmonomethoxysilane, dipentyloxymonoethoxysilane, dipentyloxymonopropoxysilane, diphenyloxylmonomethoxysilane, diphenyloxymonoethoxysilane, diphenyloxymonopropoxysilane, methoxyethoxypropoxysilane, monopropoxydimethoxy Hydrosilane compounds such as silane, monopropoxydiethoxysilane, monobutoxydimethoxysilane, monopentyloxydiethoxysilane, and monophenyloxydiethoxysilane;
- Naftilt Remethoxysilane Naftilt Riethoxysilane, Naftilt Repropoxysilane, Naftilt Lipentyloxysilane, Naftilt Riphenyloxysilane, Naftilmonomethoxydiethoxysilane, Naftylmonomethoxydipropoxysilane, Naftylmonomethoxydipentyloxysilane, Naftilmono Naftylsilane compounds such as methoxydiphenyloxysilane, naphthylmethoxyethoxypropoxysilane, and naphthylmonomethoxymonoethoxymonobutoxysilane;
- silane compound (b3) examples include dimethoxysilane, diethoxysilane, dipropoxysilane, dipentyloxysilane, diphenyloxysilane, methoxyethoxysilane, methoxypropoxysilane, methoxypentyloxysilane, methoxyphenyloxysilane, and ethoxypropoxy.
- Hydrosilane compounds such as silane, ethoxypentyloxysilane, and ethoxyphenyloxysilane;
- Methyldimethoxysilane Methylmethoxyethoxysilane, Methyldiethoxysilane, Methylmethoxypropoxysilane, Methylmethoxypentyloxysilane, Methylethoxypropoxysilane, Methyldipropoxysilane, Methyldipentyloxysilane, Methyldiphenyloxysilane, Methylmethoxyphenyloxysilane Methylhydrosilane compounds such as;
- Hydroxyphenyldimethoxysilane hydroxyphenylmethoxyethoxysilane, hydroxyphenyldiethoxysilane, hydroxyphenylmethoxypropoxysilane, hydroxyphenylmethoxypentyloxysilane, hydroxyphenylethoxypropoxysilane, hydroxyphenyldipropoxysilane, hydroxyphenyldipentyloxysilane, hydroxyphenyl Hydroxyphenylhydrosilane compounds such as diphenyloxysilane and hydroxyphenylmethoxyphenyloxysilane;
- Hydroxybenzyldimethoxysilane hydroxybenzylmethoxyethoxysilane, hydroxybenzyldiethoxysilane, hydroxybenzylmethoxypropoxysilane, hydroxybenzylmethoxypentyloxysilane, hydroxybenzylethoxypropoxysilane, hydroxybenzyldipropoxysilane, hydroxybenzyldipentyloxysilane, hydroxybenzyl Hydroxybenzylhydrosilane compounds such as diphenyloxysilane and hydroxybenzylmethoxyphenyloxysilane;
- Dimethylsilane compounds such as dimethyldimethoxysilane, dimethylmethoxyethoxysilane, dimethylmethoxypropoxysilane, dimethyldiethoxysilane, dimethyldipentyloxysilane, dimethyldiphenyloxysilane, dimethylethoxypropoxysilane, dimethyldipropoxysilane;
- Diethylsilane compounds such as diethyldimethoxysilane, diethylmethoxyethoxysilane, diethylmethoxypropoxysilane, diethyldiethoxysilane, diethyldipentyloxysilane, diethyldiphenyloxysilane, diethylethoxypropoxysilane, diethyldipropoxysilane;
- Dipropoxy such as dipropyldimethoxysilane, dipropylmethoxyethoxysilane, dipropylmethoxypropoxysilane, dipropyldiethoxysilane, dipropyldipentyloxysilane, dipropyldiphenyloxysilane, dipropylethoxypropoxysilane, dipropyldipropoxysilane Silane compound;
- Dibutylsilane compounds such as dibutyldimethoxysilane, dibutylmethoxyethoxysilane, dibutylmethoxypropoxysilane, dibutyldiethoxysilane, dibutyldipentyloxysilane, dibutyldiphenyloxysilane, dibutylethoxypropoxysilane, dibutyldipropoxysilane;
- Diphenylsilane compounds such as diphenyldimethoxysilane, diphenylmethoxyethoxysilane, diphenylmethoxypropoxysilane, diphenyldiethoxysilane, diphenyldipentyloxysilane, diphenyldiphenyloxysilane, diphenylethoxypropoxysilane, diphenyldipropoxysilane; Di (Hydroxyphenyl) Dimethoxysilane, Di (Hydroxyphenyl) methoxyethoxysilane, Di (Hydroxyphenyl) methoxypropoxysilane, Di (Hydroxyphenyl) Diethoxysilane, Di (Hydroxyphenyl) Dipentyloxysilane, Di (Hydroxyphenyl) Diphenyl Di (hydroxyphenyl) silane compounds such as oxysilane, di (hydroxyphenyl) ethoxypropoxy
- Dinaphthyl such as dinaphthyldimethoxysilane, dinaphthylmethoxyethoxysilane, dinaphthylmethoxypropoxysilane, dinaphthyldiethoxysilane, dinaphthyldipentyloxysilane, dinaphthyldiphenyloxysilane, dinaphthylethoxypropoxysilane, dinaphthyldipropoxysilane Silane compound;
- Dibenzyl such as dibenzyldimethoxysilane, dibenzylmethoxyethoxysilane, dibenzylmethoxypropoxysilane, dibenzyldiethoxysilane, dibenzyldipentyloxysilane, dibenzyldiphenyloxysilane, dibenzylethoxypropoxysilane, dibenzyldipropoxysilane Silane compound;
- Methylethyl such as methylethyldimethoxysilane, methylethylmethoxyethoxysilane, methylethylmethoxypropoxysilane, methylethyldiethoxysilane, methylethyldipentyloxysilane, methylethyldiphenyloxysilane, methylethylethoxypropoxysilane, methylethyldipropoxysilane Silane compound;
- Methylpropyl such as Methylpropyldimethoxysilane, Methylpropylmethoxyethoxysilane, Methylpropylmethoxypropoxysilane, Methylpropyldiethoxysilane, Methylpropyldipentyloxysilane, Methylpropyldiphenyloxysilane, Methylpropylethoxypropoxysilane, Methylpropyldipropoxysilane Silane compound;
- Methylbutyl such as methylbutyldimethoxysilane, methylbutylmethoxyethoxysilane, methylbutylmethoxypropoxysilane, methylbutyldiethoxysilane, methylbutyldipentyloxysilane, methylbutyldiphenyloxysilane, methylbutylethoxypropoxysilane, methylbutyldipropoxysilane, etc.
- Silane compound Silane compound
- Methyl (phenyl) dimethoxysilane Methyl (phenyl) methoxyethoxysilane, Methyl (phenyl) methoxypropoxysilane, Methyl (phenyl) diethoxysilane, Methyl (phenyl) dipentyloxysilane, Methyl (phenyl) diphenyloxysilane, Methyl (phenyl) ) Methyl (phenyl) silane compounds such as ethoxypropoxysilane and methyl (phenyl) dipropoxysilane;
- Methyl (hydroxyphenyl) silane compounds such as oxysilane, methyl (hydroxyphenyl) ethoxypropoxysilane, methyl (hydroxyphenyl) dipropoxysilane;
- Methyl (naphthyl) dimethoxysilane Methyl (naphthyl) methoxyethoxysilane, Methyl (naphthyl) methoxypropoxysilane, Methyl (naphthyl) diethoxysilane, Methyl (naphthyl) dipentyloxysilane, Methyl (naphthyl) diphenyloxysilane, Methyl (naphthyl) ) Methyl (naphthyl) silane compounds such as ethoxypropoxysilane, methyl (naphthyl) dipropoxysilane;
- Methyl (benzyl) dimethoxysilane methyl (benzyl) methoxyethoxysilane, methyl (benzyl) methoxypropoxysilane, methyl (benzyl) diethoxysilane, methyl (benzyl) dipentyloxysilane, methyl (benzyl) diphenyloxysilane, methyl (benzyl) ) Methyl (benzyl) silane compounds such as ethoxypropoxysilane, methyl (benzyl) dipropoxysilane;
- Methyl (hydroxybenzyl) silane compounds such as oxysilane, methyl (hydroxybenzyl) ethoxypropoxysilane, methyl (hydroxybenzyl) dipropoxysilane;
- Ethylpropyl such as ethylpropyldimethoxysilane, ethylpropylmethoxyethoxysilane, ethylpropylmethoxypropoxysilane, ethylpropyldiethoxysilane, ethylpropyldipentyloxysilane, ethylpropyldiphenyloxysilane, ethylpropylethoxypropoxysilane, ethylpropyldipropoxysilane Silane compound;
- Ethylbutyl such as ethylbutyldimethoxysilane, ethylbutylmethoxyethoxysilane, ethylbutylmethoxypropoxysilane, ethylbutyldiethoxysilane, ethylbutyldipentyloxysilane, ethylbutyldiphenyloxysilane, ethylbutylethoxypropoxysilane, ethylbutyldipropoxysilane Silane compound;
- Ethyl (hydroxyphenyl) silane compounds such as oxysilane, ethyl (hydroxyphenyl) ethoxypropoxysilane, ethyl (hydroxyphenyl) dipropoxysilane;
- Ethyl (hydroxybenzyl) silane compounds such as oxysilane, ethyl (hydroxybenzyl) ethoxypropoxysilane, ethyl (hydroxybenzyl) dipropoxysilane;
- Propylbutyl such as propylbutyldimethoxysilane, propylbutylmethoxyethoxysilane, propylbutylmethoxypropoxysilane, propylbutyldiethoxysilane, propylbutyldipentyloxysilane, propylbutyldiphenyloxysilane, propylbutylethoxypropoxysilane, propylbutyldipropoxysilane Silane compound;
- a propyl (hydroxyphenyl) silane compound such as oxysilane, propyl (hydroxyphenyl) ethoxypropoxysilane, propyl (hydroxyphenyl) dipropoxysilane;
- propyl (hydroxybenzyl) silane compounds such as oxysilane, propyl (hydroxybenzyl) ethoxypropoxysilane, and propyl (hydroxybenzyl) dipropoxysilane.
- silane compound (b) one type may be used alone or two or more types may be used in combination.
- the partially hydrolyzed condensate of at least one silane compound (b) is obtained by hydrolyzing and condensing the silane compound (b) or a mixture of two or more thereof by a known method.
- a predetermined amount of water and, if necessary, an organic solvent are added to the monomer of tetramethoxysilane, and the reaction is usually carried out at about room temperature to 100 ° C. while distilling off by-produced alcohol in the presence of a catalyst.
- hydrolysis and condensation of tetramethoxysilane proceed to produce a liquid tetramethoxysilane partial hydrolysis condensate (average degree of polymerization is usually about 2 to 8, most of which is 3 to 7).
- the liquid tetramethoxysilane partial hydrolysis condensate is represented by, for example, CH 3 O- (Si (OCH 3 ) 2 -O) s -CH 3 .
- s is a number of 2 to 8 representing the average degree of polymerization.
- the degree of hydrolysis can be appropriately adjusted depending on the amount of water used.
- the liquid tetramethoxysilane partial hydrolysis condensate obtained as described above may be further hydrolyzed and condensed.
- the method of further hydrolyzing and condensing the liquid tetramethoxysilane partial hydrolysis condensate is the same as the method of using the primary reaction product described later as the secondary reaction product.
- a partially hydrolyzed condensate can be obtained in the same manner.
- a mixture of two or more kinds of silane compounds (b) may be used as a partially hydrolyzed condensate.
- the catalyst examples include inorganic acids such as hydrochloric acid, acetic acid, nitrate, formic acid, sulfuric acid and phosphoric acid, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, paratoluenesulfonic acid, benzoic acid, phthalic acid and maleic acid.
- Alkaline catalysts such as potassium hydroxide, sodium hydroxide, calcium hydroxide, ammonia, organic metals, metal alkoxides, eg organic tin compounds such as dibutyltin dilaurylate, dibutyltin dioctate, dibutyltin diacetate, aluminum tris (acetylacetate).
- metal chelate compounds such as (acetylacetonate) and zirconium bis (isopropoxy) bis (acetylacetonate), and boron compounds such as borate butoxide and borate.
- an organic acid or a metal chelate compound is particularly preferable, and maleic acid or a metal acetylacetonate is particularly preferable for the production of a secondary reaction product.
- the amount of the acid catalyst used is not particularly limited as long as it can exhibit the function as a catalyst, but is usually about 0.001 to 10 parts by mass with respect to 100 parts by mass of the silane compound (b). It is selected from the range, preferably 0.003 to 5 parts by mass.
- the component (B) is a silane compound (b1) in which R 6 , R 7 , R 8 and R 9 in the formula (b1) are alkyl groups, that is, tetraalkoxysilane or a partial hydrolysis condensation thereof. It is preferably contained, more preferably it contains a partially hydrolyzed condensate of tetraalkoxysilane, and particularly preferably it contains a partially hydrolyzed condensate of tetramethoxysilane.
- the Mw of the component (B) is preferably 500 or more, more preferably 600 or more, from the viewpoint of the appearance of the cured product.
- the upper limit of Mw of the component (B) is, for example, 10,000.
- the Mw of the component (B) is a standard polystyrene-equivalent value measured by gel permeation chromatography (GPC).
- the component (B) is a partially hydrolyzed condensate of at least one silane compound (b) from the viewpoint of reactivity, and is a partially hydrolyzed condensate having an Mw of 300 to 3000 (hereinafter, “primary reactant”). (Also also referred to as)) is preferably hydrolyzed and condensed in the presence of a catalyst (hereinafter, also referred to as “secondary reactant”).
- a catalyst hereinafter, also referred to as “secondary reactant”.
- silanol groups Si—OH
- the silanol group has higher reactivity than Si-OR 5 , the curability is improved.
- the condensation reaction is promoted, the molecular weight becomes large and cracks are suppressed, so that the appearance can be improved.
- the Mw of the primary reaction product is 300 or more, the appearance of the cured product tends to be good, and when it is 3000 or less, the reactivity tends to be good.
- the Mw of the primary reaction product is preferably 400 to 2000, more preferably 500 to 1000.
- the silane compound (b) forming the primary reaction product the silane compound (b1) is preferable, the tetraalkoxysilane is more preferable, and the tetramethoxysilane is further preferable, from the viewpoint of the hardness of the cured product.
- the primary reaction product is obtained by subjecting the silane compound (b) or a mixture of two or more thereof to a hydrolysis condensation reaction.
- primary reactants can also be used, for example, MS51, MS53, MS57, MS56S manufactured by Mitsubishi Chemical, ethyl silicate 40 manufactured by Corcote, ethyl silicate 48, methyl silicate 51, methyl silicate 53A, EMS-. 485 and the like can be mentioned.
- a method of further hydrolyzing and condensing the primary reaction product in the presence of a catalyst to obtain a secondary reaction product there is a method of adding water, a catalyst and a solvent to the primary reaction product and stirring at 25 ° C. for 1 day or more. .. Further, the progress of the reaction can be promoted by heating the primary reaction product, and in that case, for example, a method of stirring at 30 ° C. to 100 ° C. for 1 hour or more can be used.
- the Mw of the secondary reaction product is preferably 400 to 50,000, more preferably 600 to 30,000, further preferably 800 to 10,000, and even more preferably 900 to 5,000, based on the empirical temperature and reaction time in the study by the present inventors. Is particularly preferable, and 1000 to 2000 is most preferable.
- the reaction of the secondary reaction product proceeds over time, it is difficult to specify its structure and characteristics (for example, size such as radius, hydroxyl value, etc.) in addition to Mw by a general analytical method. ..
- Mw can be measured, the reactivity of the present resin composition and the appearance of the cured product are different between the case where the primary reaction product is used as the component (B) and the case where the secondary reaction product is used. That is, there are circumstances (impossible / impractical circumstances) in which it is impossible or approximately impractical to directly identify the secondary reactant by its structure or properties.
- the secondary reaction product is "a partially hydrolyzed condensate of at least one silane compound (b) having a Mw of 300 to 3000, which is further hydrolyzed and condensed in the presence of a catalyst. It is more appropriate to specify.
- ⁇ Initiator (C)> When the present resin composition contains the initiator (C), the hydrolysis-condensation reaction of the component (B) and the group (1) is facilitated, and the curability of the present resin composition is improved.
- the initiator (C) include a photopolymerization initiator, a thermal polymerization initiator, a metal catalyst, an acid catalyst and the like.
- Examples of the photopolymerization initiator include a photoradical polymerization initiator, a photoacid generator, and a photobase generator.
- Examples of the thermal polymerization initiator include a thermal radical polymerization initiator, a thermal acid generator, and a thermal base generator.
- Examples of the metal catalyst or acid catalyst include catalysts similar to those used for obtaining a partially hydrolyzed condensate of the silane compound (b). Any one of these may be used alone or two or more thereof may be used in combination.
- the photopolymerization initiator is preferable as the initiator (C).
- the present resin composition contains a photopolymerization initiator
- curing of the present resin composition can be promoted by irradiation with active energy rays such as ultraviolet rays. If the resin composition is applied to a resin base material and then cured by heat, the resin base material may be deformed by heat, but if it is cured by active energy rays, the resin base material is deformed by heat. It can be applied to a resin base material having low heat resistance. Further, in general, curing by active energy rays is expected to improve productivity because the curing time is shorter than other curing methods such as thermal curing and moisture curing.
- the photopolymerization initiator As the photopolymerization initiator, the hydrolysis-condensation reaction of the component (B) and the group (1) can be started, and the present resin composition can be efficiently cured. Therefore, the photoradical polymerization initiator and the photoacid generation At least one selected from the group consisting of agents and photobase generators is preferred, at least one selected from the group consisting of photoacid generators and photobase generators is more preferred, and photoacid generators are even more preferred.
- photoradical polymerization initiator Typical examples of the photoradical polymerization initiator (hereinafter, also simply referred to as “photoinitiator”) are diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and benzyldimethylketal.
- Typical examples of photoacid generators include sulfonium salts such as triarylsulfonium hexafluorophosphate (eg, p-phenylthiophenyldiphenylsulfonium hexafluorophosphate) and triarylsulfonium hexafluoroantimonate (particularly triaryl).
- sulfonium salts such as triarylsulfonium hexafluorophosphate (eg, p-phenylthiophenyldiphenylsulfonium hexafluorophosphate) and triarylsulfonium hexafluoroantimonate (particularly triaryl).
- Sulfonium salt diaryliodonium hexafluorophosphate, diaryliodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, iodonium [4- (4-methylphenyl-2-methylpropyl) phenyl] hexafluoro Examples thereof include iodonium salts such as sulfonate.
- the photoacid generator is not limited to the exemplified compounds. One type of photoacid generator may be used alone, or two or more types may be used in combination.
- Typical examples of photobase generators are N-cyclohexylcarbamate 1- (anthraquinone-2-yl) ethyl, N, N-diethylcarbamate 9-anthrylmethyl, piperidine-1-carboxylic acid 9-an.
- the present resin composition contains a diluent
- the coating workability when the present resin composition is applied to the substrate the smoothness and uniformity of the formed coating film and its cured film, and the basis of the cured film. Adhesion to the material is improved.
- the diluent include water, an organic solvent and the like, and an organic solvent is preferable.
- the component (B) is a hydrolyzed condensate of the silane compound (b)
- the diluent may contain water compounded for hydrolyzing and condensing the silane compound (b).
- organic solvent examples include alcohol-based solvents, glycol-based solvents, hydrocarbon-based solvents, ester-based solvents, ketone-based solvents, ether-based solvents and the like.
- Examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, nbutanol, isobutanol, octanol, n-propyl alcohol, acetylacetone alcohol and the like.
- Glycol-based solvents include ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol mono n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene.
- glycol monoethyl ether examples thereof include glycol monoethyl ether, propylene glycol monobutyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate.
- hydrocarbon solvent examples include benzene, kerosene, toluene, xylene and the like.
- ester solvent examples include methyl acetate, ethyl acetate, butyl acetate, methyl acetoacetate, ethyl acetoacetate and the like.
- ketone solvent examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone and the like.
- ether solvent examples include ethyl ether, butyl ether, methyl cellosolve, ethyl cellosolve, dioxane, furan, tetrahydrofuran and the like.
- the organic solvent may be used alone or in combination of two or more.
- an alcohol solvent is preferable, and methanol, ethanol, isopropanol, or n-propanol is preferable because it is easy to handle, has good storage stability in a liquid, and has excellent characteristics of the obtained cured product. More preferred.
- ⁇ Other ingredients examples include polymers other than the copolymer (A), ultraviolet absorbers, light stabilizers, silane coupling agents, inorganic fine particles, antioxidants, anti-yellowing agents, brewing agents, pigments, and the like. Examples thereof include leveling agents, antifoaming agents, thickening agents, antisettling agents, antistatic agents and antifogging agents.
- the content of the copolymer (A) is preferably 1 to 95% by mass, more preferably 10 to 90% by mass, and further 20 to 85% by mass, based on 100% by mass of the total non-volatile components in the resin composition. Preferably, 25 to 85% by mass is particularly preferable, and 30 to 70% by mass is most preferable.
- the non-volatile component represents a component excluding the organic solvent.
- the content of the component (B) is preferably 1 to 90% by mass, more preferably 5 to 80% by mass, still more preferably 10 to 75% by mass, based on 100% by mass of the total non-volatile components in the resin composition. 20 to 70% by mass is particularly preferable, and 30 to 65% by mass is most preferable.
- the content of the component (B) is at least the above lower limit value, the strength of the cured product is more excellent, and when it is at least the above upper limit value, the appearance of the cured product is more excellent.
- the content of the initiator (C) is preferably 0.01 to 10% by mass, more preferably 0.05 to 9% by mass, and 0.1 to 0.1 to 100% by mass, based on 100% by mass of the total non-volatile components in the resin composition. 8% by mass is more preferable, 0.2 to 5% by mass is particularly preferable, and 0.2 to 3% by mass is most preferable.
- the content of the initiator (C) is at least the above lower limit value, the curability (reactivity) of the present resin composition and the productivity of the cured product are more excellent, and when it is at least the above upper limit value, the cured product is slippery. It is more water-based.
- the concentration of the non-volatile component in the present resin composition may be any concentration suitable for the coating method and is not particularly limited.
- the lower the concentration of the non-volatile component the better the smoothness and uniformity of the formed coating film and its cured film (cured product layer), and the better the adhesion between the substrate and the cured film, and the concentration of the non-volatile component.
- the higher the value the better the sagging suppressing effect when the present resin composition is applied to the substrate.
- the concentration of the non-volatile component with respect to the entire resin composition is not particularly limited, but is preferably 80% by mass or less, more preferably 0.1 to 60% by mass, still more preferably 1 to 40% by mass, and particularly preferably 1 to 30% by mass. %, Most preferably in the range of 1 to 20% by mass. By using it in the above range, a resin composition having excellent coatability can be obtained.
- the sliding angle of 20 ⁇ L of water at 23 ° C. on the surface of a cured film (initial cured film) formed by spray-coating the resin composition on a substrate and curing it is preferably 60 ° or less, preferably 50. ° or less is more preferable, 40 ° or less is further preferable, 30 ° or less is particularly preferable, and 20 ° or less is most preferable.
- the sliding angle is measured while changing the tilt angle by 1 °. Details are as described in Examples described later. Conventionally, the sliding angle is often measured while continuously changing the inclination angle. The sliding angle measured while changing the tilt angle by 1 ° tends to be larger than the sliding angle measured while continuously changing the tilt angle.
- the sliding angle can be adjusted by adjusting the content and type of the polyalkylsiloxane unit in the resin composition. Specifically, the content of the copolymer (A) is increased, the proportion of the silicone macromonomer (X) to be copolymerized in the copolymer (A) is increased, or the silicone macromonomer (X) is longer. Choosing one containing a chain polyalkylsiloxane unit tends to reduce the water sliding angle of the initial cured film.
- the sliding angle after the durability test is particularly important in a wide range of application development, and a lower one is preferable, and a smaller change from the initial stage is preferable.
- the surface of the cured film is 23 ° C.
- the sliding angle of 20 ⁇ L of water is preferably 60 ° or less, more preferably 50 ° or less, further preferably 40 ° or less, particularly preferably 30 ° or less, and most preferably 20 ° or less.
- the amount of change in the water sliding angle of the cured film after the durability test from the initial water sliding angle is as follows. 40 ° or less is preferable, 30 ° or less is more preferable, 20 ° or less is further preferable, and 15 ° or less is most preferable. There is no particular lower limit, but it is preferably 0 °. Within this range, the same level of performance as in the initial stage can be exhibited over a long period of time, and product design becomes easier.
- the sliding angle after the weather resistance test is particularly important in a wide range of application development, and a lower one is preferable, and a smaller change from the initial stage is preferable.
- a cured film is formed as described above, and the conditions are 12 minutes of rainfall in 60 minutes, irradiation intensity 180 W / m 2 (300 to 400 nm), black panel temperature 63 ° C, tank temperature 50 ° C, and tank humidity 50%.
- the sliding angle of 20 ⁇ L of water at 23 ° C. on the surface of the cured film (cured film after the durability test) after the weather resistance test for 500 hours is preferably 60 ° or less, more preferably 50 ° or less. It is preferable, more preferably 40 ° or less, particularly preferably 30 ° or less, and most preferably 20 ° or less.
- There is no particular limitation on the lower limit of the sliding angle of water for example, 1 ° or more.
- the amount of change in the water sliding angle of the cured film after the weather resistance test from the initial water sliding angle is as follows. 40 ° or less is preferable, 30 ° or less is more preferable, 20 ° or less is further preferable, and 15 ° or less is most preferable. There is no particular lower limit, but it is preferably 0 °. Within this range, the same level of performance as in the initial stage can be exhibited over a long period of time, and product design becomes easier.
- the present resin composition can be produced by mixing a copolymer (A), a component (B), an initiator (C) if necessary, a diluent, and other components.
- the diluent contains water
- the water may be added at the time of preparing the hydrolyzed condensate of the silane compound (b), may be added at the time of producing the present resin composition, and the water of the silane compound (b) may be added. It may be blended both at the time of preparing the decomposition condensate and at the time of producing the present resin composition.
- the present resin composition described above contains the copolymer (A), the component (B), and the initiator (C), a cured product having excellent appearance, water slipperiness, weather resistance, and durability is formed. can.
- This resin composition is used for sensing members such as surface materials of members through which electromagnetic waves of sensing members (millimeter wave radar, LiDAR, etc.) pass; various lamp lenses for automobiles (lighting equipment for vehicles) and hard coating agents for resin glazing. It can be used for road signs, traffic signals, camera lenses, 5G-related members, antennas, solar panels, window glass, resin glass, automobile glass, and the like.
- the use of the present resin composition is preferably a sensing member.
- the surface material of the emblem or front grill located on the front side of the millimeter wave radar or LiDAR in a vehicle is composed of a cured product of this resin composition, even if raindrops or snow adhere to the outermost surface of the emblem or the like, it is easy. It can prevent the electromagnetic waves of millimeter-wave radar and LiDAR from being attenuated or scattered by raindrops or snow.
- the cured product according to one aspect of the present invention (hereinafter, also referred to as “this cured product”) is a cured product of the present resin composition.
- the present cured product is obtained by curing the present resin composition.
- the curing method include a method of irradiating the resin composition with active energy rays, a method of curing by heating, a method of curing by utilizing the moisture in the air, and the like, from the viewpoint of the temperature applied to the substrate and productivity. Therefore, a method of irradiating the present resin composition with active energy rays is preferable.
- Examples of the active energy ray include ultraviolet rays and electron beams.
- Ultraviolet rays are preferable because they can be easily used and have excellent polymerizable properties.
- a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, a UV-LED, a low-pressure mercury lamp, a xenon excimer lamp, or the like can be used as a light source. From the viewpoint of productivity, it is preferable to use a light source that exhibits maximum irradiation intensity at a wavelength of 150 to 420 nm.
- the integrated irradiation amount of ultraviolet rays is preferably 50 to 3000 mJ / cm 2 , more preferably 100 to 2000 mJ / cm 2 .
- the active energy ray may be irradiated in an air atmosphere or in an inert gas atmosphere such as nitrogen or argon.
- the time for irradiating the active energy rays is preferably in the range of 1 minute or less, more preferably 30 seconds or less, and further preferably 15 seconds or less in relation to the appearance and intensity of the cured product. There is no particular lower limit, but it is, for example, 0.1 seconds.
- the method of curing by irradiating with active energy rays can be cured in a shorter time than the method of thermosetting, and is therefore a preferable form in consideration of productivity and cost.
- the present resin composition may be heat-treated in order to remove the diluent before irradiating the present resin composition with active energy rays.
- This heat treatment can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the resin composition may be heat-treated after being irradiated with active energy rays.
- This heat treatment can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the cured product obtained by heat treatment after curing by irradiation with active energy rays tends to have excellent hardness and durability because the condensation reaction rate is higher than that without heat treatment.
- the sliding angle of water at 23 ° C. and 20 ⁇ L on the surface of the cured product (initial cured product) formed as described above is preferably as low as possible, preferably 60 ° or less, more preferably 50 ° or less, and more preferably 40 °. The following is more preferable, 30 ° or less is particularly preferable, and 20 ° or less is most preferable. There is no particular limitation on the lower limit of the sliding angle of water, and it is 0 ° or more. If the sliding angle of water is not more than the above upper limit, raindrops and snow adhering to the surface can easily slide down.
- the sliding angle of water after the durability test is particularly important in a wide range of application development, and a lower one is preferable, and a smaller change from the initial stage is preferable.
- the surface of the cured product (cured product after the durability test) is 23 ° C.
- the sliding angle of 20 ⁇ L of water is preferably 60 ° or less, more preferably 50 ° or less, further preferably 40 ° or less, particularly preferably 30 ° or less, and most preferably 20 ° or less.
- the amount of change in the water slide angle of the cured product after the durability test from the initial water slide angle is as follows. 40 ° or less is preferable, 30 ° or less is more preferable, 20 ° or less is further preferable, and 15 ° or less is most preferable. There is no particular lower limit, but it is preferably ⁇ 40 °. Within this range, the same level of performance as in the initial stage can be exhibited over a long period of time, and product design becomes easier.
- the cured product described above is a cured product of a resin composition containing the copolymer (A) and the component (B), and is therefore excellent in productivity, appearance, water permeability and durability.
- This cured product is used for sensing members such as the surface material of members through which electromagnetic waves of sensing members (millimeter wave radar, LiDAR, etc.) pass; various automobile lamp lenses (vehicle lamps), hard coats for resin glazing, road signs, etc. , Traffic traffic lights, camera lenses, 5G-related members, antennas, solar panels, window glass, resin glass, automobile glass, and the like.
- sensing members such as the surface material of members through which electromagnetic waves of sensing members (millimeter wave radar, LiDAR, etc.) pass; various automobile lamp lenses (vehicle lamps), hard coats for resin glazing, road signs, etc. , Traffic traffic lights, camera lenses, 5G-related members, antennas, solar panels, window glass, resin glass, automobile glass, and the like.
- the sensing member is the most suitable application for the cured product.
- a curable composition containing a copolymer (A) and a component (B) composed of at least one silane compound (b) or a partially hydrolyzed condensate thereof is coated on a substrate. It can be manufactured by working and curing (cured product forming step). After the cured product forming step, the formed cured product and the substrate may be peeled off, if necessary.
- the curable composition contains the copolymer (A) and the component (B).
- the curable composition typically comprises a diluent.
- the curable composition preferably contains the initiator (C).
- the curable composition may contain other components other than the above, if necessary.
- the copolymer (A), initiator (C), and other components are as described above.
- the component (B) comprises at least one silane compound (b) or a partially hydrolyzed condensate thereof.
- the silane compound (b) is as described above.
- the partially hydrolyzed condensate of at least one silane compound (b) is obtained by hydrolyzing and condensing the silane compound (b) or a mixture of two or more thereof by a known method.
- a predetermined amount of water and, if necessary, an organic solvent are added to the monomer of tetramethoxysilane, and the reaction is usually carried out at about room temperature to 100 ° C. while distilling off by-produced alcohol in the presence of a catalyst.
- hydrolysis and condensation of tetramethoxysilane proceed to produce a liquid tetramethoxysilane partial hydrolysis condensate (average degree of polymerization is usually about 2 to 8, most of which is 3 to 7).
- the liquid tetramethoxysilane partial hydrolysis condensate is represented by, for example, CH 3 O- (Si (OCH 3 ) 2 -O) s -CH 3 .
- s is a number of 2 to 8 representing the average degree of polymerization.
- the degree of hydrolysis can be appropriately adjusted depending on the amount of water used.
- the liquid tetramethoxysilane partial hydrolysis condensate obtained as described above may be further hydrolyzed and condensed.
- the method of further hydrolyzing and condensing the liquid tetramethoxysilane partial hydrolysis condensate is the same as the method of using the primary reaction product described later as the secondary reaction product.
- a partially hydrolyzed condensate can be obtained in the same manner.
- a mixture of two or more kinds of silane compounds (b) may be used as a partially hydrolyzed condensate.
- the catalyst examples include inorganic acids such as hydrochloric acid, acetic acid, nitrate, formic acid, sulfuric acid and phosphoric acid, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, paratoluenesulfonic acid, benzoic acid, phthalic acid and maleic acid.
- Alkaline catalysts such as potassium hydroxide, sodium hydroxide, calcium hydroxide, ammonia, organic metals, metal alkoxides, eg organic tin compounds such as dibutyltin dilaurylate, dibutyltin dioctate, dibutyltin diacetate, aluminum tris (acetylacetate).
- metal chelate compounds such as (acetylacetonate) and zirconium bis (isopropoxy) bis (acetylacetonate)
- boron compounds such as borate butoxide and borate.
- the amount of the acid catalyst used is not particularly limited as long as it can exhibit the function as a catalyst, but is usually about 0.001 to 10 parts by mass with respect to 100 parts by mass of the silane compound (b). It is selected from the range, preferably 0.003 to 5 parts by mass.
- the component (B) is a silane compound (b1) in which R 6 , R 7 , R 8 and R 9 in the formula (b1) are alkyl groups, that is, tetraalkoxysilane or a partial hydrolysis thereof, from the viewpoint of the hardness of the cured product. It is preferably a decomposition condensate, more preferably a partial hydrolysis condensate of tetraalkoxysilane, and particularly preferably a partial hydrolysis condensate of tetramethoxysilane, from the viewpoint of the sliding angle of water.
- the Mw of the component (B) is preferably 500 or more, more preferably 600 or more, from the viewpoint of appearance.
- the upper limit of Mw of the component (B) is, for example, 10,000.
- the Mw of the component (B) is a standard polystyrene-equivalent value measured by gel permeation chromatography (GPC).
- the component (B) is a partially hydrolyzed condensate of at least one silane compound (b) and has a Mw of 300 to 3000 (hereinafter, "primary reactant”). (Also referred to as)) is preferably hydrolyzed and condensed in the presence of a catalyst (hereinafter, also referred to as “secondary reactant”).
- a catalyst hereinafter, also referred to as “secondary reactant”.
- silanol group Si—OH
- Si-OR 5 Since the silanol group has higher reactivity than Si-OR 5 , the curability is improved. In addition, since the condensation reaction is promoted, the molecular weight becomes large and cracks are suppressed, so that the appearance can be improved.
- the Mw of the primary reaction product is 300 or more, the appearance of the cured product tends to be good, and when it is 3000 or less, the reactivity tends to be good.
- the Mw of the primary reaction product is preferably 400 to 2000, more preferably 500 to 1000.
- the silane compound (b) forming the primary reaction product the silane compound (b1) is preferable, tetraalkoxysilane is more preferable, and tetramethoxysilane is further preferable, from the viewpoint of the hardness of the cured layer.
- the primary reaction product is obtained by subjecting the silane compound (b) or a mixture of two or more thereof to a hydrolysis condensation reaction.
- primary reactants can also be used, for example, MS51, MS53, MS57, MS56S manufactured by Mitsubishi Chemical, ethyl silicate 40 manufactured by Corcote, ethyl silicate 48, methyl silicate 51, methyl silicate 53A, EMS-. 485 and the like can be mentioned.
- Examples of the method for hydrolyzing and condensing the primary reaction product in the presence of a catalyst include a method in which water, a catalyst and a solvent are added to the primary reaction product and the mixture is stirred at 25 ° C. for 1 day or longer. Further, the progress of the reaction can be promoted by heating the primary reaction product, and in that case, for example, a method of stirring at 30 ° C. to 100 ° C.
- the Mw of the secondary reaction product is preferably 400 to 50,000, more preferably 600 to 30,000, further preferably 800 to 10,000, and even more preferably 900 to 5,000, based on the empirical temperature and reaction time in the study by the present inventors. Is particularly preferable, and 1000 to 2000 is most preferable.
- the reaction of the secondary reaction product proceeds over time, it is difficult to specify its structure and characteristics (for example, size such as radius, hydroxyl value, etc.) in addition to Mw by a general analytical method. ..
- Mw can be measured, the reactivity of the curable composition and the appearance of the cured product differ between the case where the primary reaction product is used as the component (B) and the case where the secondary reaction product is used. That is, there are circumstances (impossible / impractical circumstances) in which it is impossible or approximately impractical to directly identify the secondary reactant by its structure or properties.
- the secondary reaction product is "a partially hydrolyzed condensate of at least one silane compound (b) having a Mw of 300 to 3000, which was hydrolyzed and condensed in the presence of a catalyst. It is more appropriate to specify.
- the coating workability when applying the curable composition, the smoothness and uniformity of the cured product formed, and the adhesion between the substrate and the cured product are improved. improves.
- the diluent include water, an organic solvent and the like, and an organic solvent is preferable.
- the organic solvent include alcohol-based solvents, glycol-based solvents, hydrocarbon-based solvents, ester-based solvents, ketone-based solvents, ether-based solvents and the like.
- Examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, nbutanol, isobutanol, octanol, n-propyl alcohol, acetylacetone alcohol and the like.
- Glycol-based solvents include ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol mono n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene.
- glycol monoethyl ether examples thereof include glycol monoethyl ether, propylene glycol monobutyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate.
- hydrocarbon solvent examples include benzene, kerosene, toluene, xylene and the like.
- ester solvent examples include methyl acetate, ethyl acetate, butyl acetate, methyl acetoacetate, ethyl acetoacetate and the like.
- ketone solvent examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone and the like.
- ether solvent examples include ethyl ether, butyl ether, methyl cellosolve, ethyl cellosolve, dioxane, furan, tetrahydrofuran and the like.
- the organic solvent may be used alone or in combination of two or more.
- the diluent an alcohol solvent is preferable, and methanol, ethanol, isopropanol or n-propanol is more preferable because it is easy to handle, has good storage stability in a liquid, and has excellent characteristics of the obtained cured product. preferable.
- the diluent may contain water compounded for hydrolyzing and condensing the silane compound (b).
- the content of the copolymer (A) is preferably 1 to 95% by mass, more preferably 10 to 90% by mass, and 20 to 20 to 100% by mass with respect to 100% by mass of the non-volatile component in the curable composition. 85% by mass is more preferable, 25 to 85% by mass is particularly preferable, and 30 to 65% by mass is most preferable.
- the content of the copolymer (A) is at least the above lower limit value, the water-sliding property and appearance of the cured product are more excellent, and when it is at least the above upper limit value, the appearance and strength of the cured product are more excellent.
- the content of the component (B) is preferably 1 to 90% by mass, more preferably 5 to 80% by mass, still more preferably 10 to 75% by mass, and 18% by mass with respect to 100% by mass of the non-volatile component in the curable composition. ⁇ 70% by mass is particularly preferable, and 30 to 65% by mass is most preferable.
- the content of the component (B) is at least the above lower limit value, the durability and strength of the cured product are more excellent, and when it is at least the above upper limit value, the appearance of the cured product is more excellent.
- the content of the initiator (C) is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less, based on 100% by mass of the non-volatile component in the curable composition.
- the lower limit is not particularly limited, but in the case of a cured product cured by irradiation with active energy rays, 0.01% by mass or more is preferable, 0.05% by mass or more is more preferable, and 0.2% by mass or more is further preferable. preferable.
- the concentration of the non-volatile component with respect to the entire curable composition is not particularly limited, but is preferably 80% by mass or less, more preferably 0.1 to 60% by mass, still more preferably 1 to 40% by mass, and particularly preferably 1 to 30%. It is in the range of% by mass, most preferably 1 to 20% by mass. By using it in the above range, a composition having excellent coatability can be obtained.
- the non-volatile component represents a component excluding the diluent.
- the content of other components is not particularly limited, but can be, for example, about 0 to 30% by mass with respect to 100% by mass of the non-volatile component in the curable composition.
- the curable composition can be prepared by mixing the copolymer (A), the component (B), and if necessary, the diluent, the initiator (C), and other components.
- the diluent contains water
- the water may be added during the preparation of the hydrolyzed condensate of the silane compound (b), may be added during the production of the curable composition, and the water of the silane compound (b) may be added. It may be blended both at the time of preparing the decomposition condensate and at the time of producing the present composition.
- ⁇ Curing product formation process> Known methods such as brush coating, gravure coater method, die coater method, bar coater method, spray coating method, flow coating method, dip coating method, spin coating method and curtain coating method are used as coating methods for the curable composition. Can be used.
- Examples of the curing method include a method of irradiating the curable composition with active energy rays, a method of curing by heating, a method of curing by utilizing the humidity in the air, and the like.
- a method of irradiating the curable composition with active energy rays may be preferable.
- the heating method When the curable composition is cured by heating, examples of the heating method include irradiation with a near-infrared lamp, circulation of warm air, and the like. As the heating conditions, heating at 60 ° C. to 200 ° C. for 10 minutes to 3 hours is preferable, and heating at 80 ° C. to 150 ° C. for 30 minutes to 2 hours is more preferable.
- the curable composition may be heated in an air atmosphere or in an atmosphere of an inert gas such as nitrogen or argon.
- the active energy rays include ultraviolet rays and electron beams.
- Ultraviolet rays are preferable from the viewpoint of ease of introduction of equipment and cost.
- a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, a UV-LED, a low-pressure mercury lamp, a xenon excimer lamp, or the like can be used as a light source. From the viewpoint of productivity, it is preferable to use a light source that exhibits maximum irradiation intensity at a wavelength of 150 to 420 nm.
- the integrated irradiation amount of ultraviolet rays is preferably 50 to 3000 mJ / cm 2 , more preferably 100 to 2000 mJ / cm 2 .
- the active energy rays may be irradiated in an air atmosphere or in an atmosphere of an inert gas such as nitrogen or argon.
- the curable composition contains a diluent
- the curable composition is used to remove the diluent after coating the curable composition and before irradiating the curable composition with active energy rays for drying.
- the object may be heat-treated. This heat treatment can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the cured product obtained by irradiating the cured product with active energy rays after the heat treatment does not easily leave a diluent inside the cured product, so that the long-term adhesion outdoors is improved as compared with the product without the heat treatment. Tend to do.
- the surface temperature of the substrate (hereinafter referred to as heating temperature) is preferably 40 to 90 ° C, more preferably 50 to 70 ° C, and dried.
- the time is preferably 60 to 180 seconds, more preferably 90 to 150 seconds.
- the curable composition may be heat-treated after being irradiated with active energy rays.
- This heat treatment can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the cured product obtained by heat treatment after curing by irradiation with active energy rays tends to have excellent hardness and durability because the condensation reaction rate is higher than that without heat treatment.
- the contact angle of 1 ⁇ L distilled water at 23 ° C. (hereinafter, also referred to as “water contact angle”) on the surface of the initial cured layer is preferably 70 ° or higher, more preferably 80 ° or higher, and further preferably 90 ° or higher. It is preferable, 95 ° or more is particularly preferable, and 100 ° or more is most preferable. When the contact angle is at least the above lower limit value, the antifouling property is more excellent.
- the upper limit is not particularly limited, but is preferably 150 °.
- the contact angle of water can be adjusted by the content of the copolymer (A), the content of the silicone macromonomer (X) in the copolymer (A), and the like. Specifically, when the content of the copolymer (A) is increased or the content of the silicone macromonomer (X) in the copolymer (A) is increased, the contact angle tends to increase.
- the thickness of the cured product formed on the substrate is preferably 10 nm to 4 ⁇ m, more preferably 20 nm to 3 ⁇ m.
- the thickness of the cured product is at least the above lower limit value, the water-sliding property and scratch resistance of the cured product are more excellent, and when it is at least the above upper limit value, cracks are less likely to occur in the cured product.
- the cured product described above contains the copolymer (A) and the component (B), it is excellent in water-sliding property, appearance and durability.
- the cured product is used for sensing members such as members through which electromagnetic waves of sensing members (millimeter wave radar, LiDAR, etc.) pass; various automobile lamp lenses (vehicle lamps), resin glazing, road signs, traffic signals, camera lenses, etc. It can be used for 5G-related members, antennas, solar panels, window glass, resin glass, automobile glass and the like.
- sensing member application is preferable as the application of the cured product.
- the laminate according to one aspect of the present invention (hereinafter, also referred to as “the present laminate”) has a base material and a layer made of a cured product (hereinafter, also referred to as a “cured product layer”).
- the cured product layer is preferably located on the outermost surface layer of the present laminated body.
- a primer layer may be provided between the base material and the cured product layer.
- the laminate When a resin base material is used as the base material, the laminate preferably contains at least one selected from the group consisting of an ultraviolet absorber and a light stabilizer.
- the laminate contains an ultraviolet absorber and a light stabilizer, deterioration of the laminate itself and the member underlying the laminate due to ultraviolet rays and the like is suppressed, and weather resistance and durability are improved.
- the UV absorber and the light stabilizer will be described in detail later.
- the ultraviolet absorber and the light stabilizer may be contained in any layer of the laminate.
- the ultraviolet absorber and the light stabilizer are contained in the base material or the primer layer, and the laminated body. Considering the ease of designing the whole, it is more preferable to be contained in the primer layer.
- the base material or the primer layer contains a light stabilizer
- the primer layer contains a light stabilizer. Since the light stabilizer can capture radicals generated by light, it can improve resistance to light (particularly ultraviolet rays). In particular, it is preferable that an ultraviolet absorber is contained together with the light stabilizer.
- the content of the ultraviolet absorber or light stabilizer cannot be unequivocally determined because it depends on the layer used in the laminate and the film thickness of the layer.
- the content of each of the ultraviolet absorber and the light stabilizer is usually 10% by mass or less, preferably 0.01, based on the total mass of the base material. It is in the range of ⁇ 5% by mass, more preferably 0.1 to 3% by mass.
- the content of each of the UV absorber and the light stabilizer is preferably 30% by mass or less, more preferably 0.01 with respect to the total mass of the primer layer.
- It is in the range of about 20% by mass, more preferably 0.1 to 15% by mass, and particularly preferably 0.3 to 15% by mass. By using it in the above range, it is possible to improve the weather resistance of the base material and the member while maintaining other characteristics, and it is possible to prevent deterioration.
- base material glass base material; metal base material such as zinc-plated steel plate, zinc alloy-plated steel plate, stainless steel plate, tin-plated steel plate; polymethyl methacrylate resin, polycarbonate resin, polyester resin, polystyrene resin, ABS resin, AS resin Examples thereof include resin base materials such as polyamide resin, polyarylate resin, polyurethane resin, polyvinyl resin, triacetyl cellulose, polymethacrylicimide resin and polyallyl diglycol carbonate resin.
- the resin constituting the resin base material is glass, polycarbonate resin, polyester resin, triacetyl cellulose, polyurethane resin or polyvinyl resin from the viewpoint of transparency and mechanical strength.
- the resin substrate is added with an ultraviolet absorber, a light stabilizer, a plasticizer, an antistatic agent, a flame retardant, a reinforcing material, a filler, a colorant, a lubricant, a foaming agent, an easy lubricant, a curing catalyst, etc. It may contain an agent. If necessary, a primer layer may be present on the substrate for improving adhesion, etc., and an adhesive layer, an antifogging layer, etc. may be present on the side opposite to the side where the cured product layer of the substrate is present. It is also possible to have a functional layer such as an antireflection layer. Further, the heater may be mounted on the side opposite to the outermost surface of the laminated body or inside.
- the primer layer contributes to the adhesion between the base material and the cured layer and the improvement of the coatability when laminating the cured layer.
- the primer layer typically contains a resin component.
- the primer layer preferably contains at least one selected from the group consisting of an ultraviolet absorber and a light stabilizer. If necessary, the primer layer may contain additives other than the ultraviolet absorber and the light stabilizer as long as the effects of the present invention are not impaired.
- the resin component examples include acrylic resin, polyester resin, urethane resin, vinyl resin and the like. Among these, acrylic resin or urethane resin is particularly preferable from the viewpoint of improving adhesion. These resin components may be used alone or in combination of two or more. Further, the resin component may be a non-curable resin or a compound derived from a curable compound (monomer, oligomer, etc.). Examples of the compound derived from the curable compound include a cured product of the curable compound. The compound derived from the curable compound is preferable from the viewpoint of further improving the adhesion to the cured layer and improving the durability of the cured layer.
- a primer layer containing a compound derived from a curable compound is formed by containing a curable compound in the primer forming the primer layer, applying the primer on the substrate, and curing the curable compound on the substrate. ..
- the primer layer has excellent adhesion to the substrate and improves the adhesion between the substrate and the cured layer, as compared with the case where the resin component is only a non-curable resin.
- the durability of the cured layer is compared with the case where a non-curable compound is used. Tends to be excellent.
- the curable compound examples include an active energy ray-curable compound and a thermosetting compound, and an active energy ray-curable compound is preferable. If the primer is applied to the resin base material and then cured by heat, the resin base material may be deformed by heat, but if it is cured by active energy rays, the deformation of the resin base material by heat can be suppressed. It can also be applied to resin substrates with low heat resistance. Further, in general, curing by active energy rays is expected to improve productivity because the curing time is shorter than other curing methods such as heat curing and moisture curing.
- the active energy ray-curable compound a conventionally known active energy ray-curable compound can be used, and examples thereof include compounds having a radically polymerizable group such as a (meth) acryloyl group.
- the compound having a radically polymerizable group various conventionally known compounds can be used, and examples thereof include (meth) acrylate and other monomers copolymerizable with (meth) acrylate.
- the compounds having a radically polymerizable group include a monofunctional compound having one radically polymerizable group, a bifunctional compound having two radically polymerizable groups, and a trifunctional or more polyfunctional compound having three or more radically polymerizable groups. Examples include functional compounds. Among these, it is preferable to contain a polyfunctional compound in order to form a primer layer having an increased degree of curing in order to improve the adhesion to the cured layer.
- polyfunctional compound examples include polyfunctional (meth) acrylates.
- the polyfunctional (meth) acrylate is not particularly limited, but for example, pentaerythritol triacrylate, dipentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, and trimethylolpropane.
- Polyester (meth) acrylates such as polyester oligomers having an acryloyl group (specifically, M8030, M7100, etc. manufactured by Toa Synthetic); isocyanurates of isophorone diisocyanate (IPDI), polytetramethylene glycol (PTMG) and hydroxyethyl.
- Polyfunctional urethane (meth) acrylates such as acrylate (HEA) reactants, pentaerythritol triacrylate reactants to hexamethylene diisocyanate (HDI) and PTMG reactants; oligoesters and pentaerythritol triacrylates using polycarbonate diols.
- Polyester (meth) acrylate having a carbonate bond such as a reactant
- Polyurethane (meth) acrylate such as a reactant of diisocyanate and a trifunctional or higher polyol and a reaction product of a hydroxyl group-containing (meth) acrylate
- Examples thereof include triethoxy (meth) acrylates having an isocyanurate ring; these alkylene oxide modified products; and these polycaprolactone modified products.
- pentaerythritol triacrylate pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, trimethylolpropane triacrylate, and trimethylolpropane tetraacrylate.
- Acrylate, dipentaerythritol triacrylate; these alkylene oxide modified products; these caprolactone modified products are preferably contained.
- the (meth) acrylate may be used alone or in combination of two or more.
- Examples of the monofunctional compound include monofunctional (meth) acrylate and (meth) acrylic acid.
- the monofunctional (meth) acrylate is not particularly limited, but is, for example, methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, and stearyl (meth).
- Alkyl (meth) acrylates such as acrylates, cyclohexyl (meth) acrylates and isobornyl (meth) acrylates, hydroxyalkyl (meth) acrylates such as hydroxyethyl (meth) acrylates, hydroxypropyl (meth) acrylates and hydroxybutyl (meth) acrylates.
- Amino group-containing (meth) acrylates such as aromatic (meth) acrylates, diaminoethyl (meth) acrylates, diethylaminoethyl (meth) acrylates, methoxyethylene glycol (meth) acrylates, phenoxypolyethylene grease (meth) acrylates, and phenylphenols.
- ethylene oxide-modified (meth) acrylate such as ethylene oxide-modified (meth) acrylate, glycidyl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate.
- the bifunctional polyfunctional (meth) acrylate is not particularly limited, but for example, 1,4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and 1,6-hexanediol di.
- Modified products; Examples thereof include these polycaprolactone modified products.
- thermosetting compound a conventionally known thermosetting compound can be used.
- various polyols and various polyisocyanates are used in combination.
- polystyrene resin examples include conventionally known ones, and examples thereof include polymers such as polycarbonate polyol, polyester polyol, acrylic polyol, polyurethane polyol, polyolefin polyol, polyether polyol, and polyvinyl alcohol, and terminals such as dendrimer and hyperbranched polymer.
- Polymers with a dendritic branched structure that are hydroxyl groups ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol , 1,5-Pentanediol, 1,6-hexanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol , 1,10-decanediol, neopentaneglycol, 3-methyl-1,5-pentanediol, 3,3-dimethylolheptan, trimethylolethane, trimethylolpropane, glycerol, polycaprolactone triol, erythritol, pentaerythr
- a polymer type or a polyol having a branched structure is preferable because the cross-linking density is high and the curability and durability are excellent. Among them, a highly branched structure is formed and the cross-linking density is effectively high. Dendrimers and hyperbranched polymers are more preferred from the standpoint of being able to be made and improving durability. These polyols may be used alone or in combination of two or more.
- polyisocyanate examples include those conventionally known, and examples thereof include aromatic diisocyanates such as tolylene diisocyanate, xylylene diisocyanate, methylene diphenyl diisocyanate, phenylenedi isocyanate, naphthalenedi isocyanate, and trizine diisocyanate, ⁇ , ⁇ , ⁇ ', and ⁇ .
- aromatic diisocyanates such as tolylene diisocyanate, xylylene diisocyanate, methylene diphenyl diisocyanate, phenylenedi isocyanate, naphthalenedi isocyanate, and trizine diisocyanate, ⁇ , ⁇ , ⁇ ', and ⁇ .
- '-Aliphatic diisocyanate having an aromatic ring such as tetramethylxylylene diisocyanate, methylene diisocyanate, propylene diisocyanate, lysine diisocyanate, trimethylhexamethylene diisocyanate, aliphatic diisocyanate such as hexamethylene diisocyanate, cyclohexanediisocyanate, methylcyclohexanediisocyanate, isophorone diisocyanate, Examples thereof include alicyclic diisocyanates such as dicyclohexammethane diisocyanate and isopropyridene dicyclohexyldiisocyanate.
- trifunctional or higher polyisocyanates such as a burette body, a trimethylolpropane adduct body, an isocyanurate body, and an allophanate body synthesized using these bifunctional polyisocyanates as starting materials can also be mentioned. These may be used alone or in combination of two or more.
- a trifunctional or higher functional polyisocyanate it is preferable to contain a trifunctional or higher functional polyisocyanate, and it is more preferable to contain an isocyanurate form, because the crosslink density is high and the curability and durability are excellent.
- an aromatic ring structure or an alicyclic structure are preferable, and from the viewpoint of being less likely to turn yellow, those having an aliphatic structure or an alicyclic structure are preferable.
- the content of the resin component is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, and may be 100% by mass with respect to the total mass of the primer layer. ..
- UV absorber examples include an organic ultraviolet absorber and an inorganic ultraviolet absorber. From the viewpoint of transparency, an organic ultraviolet absorber is preferable.
- the organic ultraviolet absorber is not particularly limited, and is, for example, a hydroxyphenyltriazine ultraviolet absorber, a benzotriazole ultraviolet absorber, a cyclic imino ester ultraviolet absorber, a benzophenone ultraviolet absorber, and a salicylate ester ultraviolet absorber. , Cyanoacrylate-based ultraviolet absorbers and the like.
- hydroxyphenyltriazine-based UV absorbers are more preferable, and hydroxyphenyltriazine-based UV absorbers are even more preferable, from the viewpoint of weather resistance and durability.
- These ultraviolet absorbers may be used alone or in combination of two or more. Furthermore, it is also possible to use those in which these compounds are incorporated into a polymer.
- the hydroxyphenyltriazine-based ultraviolet absorber is not limited to the following, but is, for example, 2- [4-([2-hydroxy-3-dodecyloxypropyl] oxy) -2-hydroxyphenyl] -4, 6-bis (2,4-dimethylphenyl) -1,3,5-triazine and 2- [4-([2-hydroxy-3-tridecyloxypropyl] oxy) -2-hydroxyphenyl] -4,6 -Bis (2,4-dimethylphenyl) -1,3,5-triazine (Tinuvin (registered trademark) (registered trademark) 400 manufactured by BASF), 2- [4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine-2-yl] -5- [3- (dodecyloxy) -2-hydroxypropoxy] phenol), 2- (2,4-dihydroxyphenyl) -4,6-bis- ( Reaction product of 2,4-
- the benzotriazole-based ultraviolet absorber is not limited to the following, but is, for example, 2- [2'-hydroxy-5'-(methacryloxymethyl) phenyl] -2H-benzotriazole, 2- [2'. -Hydroxy-5'-(methacryloyloxyethyl) phenyl] -2H-benzotriazole, 2- [2'-hydroxy-5'-(methacryloyloxypropyl) phenyl] -2H-benzotriazole, 2- [2'-hydroxy -5'-(methacryloyloxyhexyl) phenyl] -2H-benzotriazole, 2- [2'-hydroxy-3'-tert-butyl-5'-(methacryloxyethyl) phenyl] -2H-benzotriazole, 2- [2'-Hydroxy-5'-tert-butyl-3'-(methacryloyloxyethyl) phenyl
- the cyclic iminoester-based ultraviolet absorber is not limited to the following, but is, for example, 2-methyl-3,1-benzoxazine-4-one, 2-butyl-3,1-benzoxazine-4-one.
- benzophenone-based ultraviolet absorber (benzophenone-based compound) and oxybenzophenone-based ultraviolet absorber (oxybenzophenone-based compound) include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, and 2-hydroxy-4-.
- Methoxybenzophenone-5-sulfonic acid anhydrous and trihydrate
- 2-hydroxy-4-octyloxybenzophenone 4-dodecyloxy-2-hydroxybenzophenone
- 4-benzyloxy-2-hydroxybenzophenone 2,2'- Dihydroxy-4-methoxybenzophenone (trade name "KEMISORB111”, manufactured by Chemipro Kasei Co., Ltd.), 2,2', 4,4'-tetrahydroxybenzophenone (trade name "SEESORB106", manufactured by Cipro Kasei Co., Ltd.), 2,2 '-Dihydroxy-4,4-dimethoxybenzophenone and the like can be mentioned.
- salicylic acid ester-based ultraviolet absorber examples include phenyl-2-acryloyloxybenzoate, phenyl-2-acryloxy-3-methylbenzoate, and phenyl-2-acryloyloxy-4.
- cyanoacrylate-based ultraviolet absorber examples include alkyl-2-cyanoacrylate, cycloalkyl-2-cyanoacrylate, alkoxyalkyl-2-cyanoacrylate, alkenyl-2-cyanoacrylate, and alkynyl-2. -Cyanoacrylate and the like can be mentioned.
- the light stabilizer is not particularly limited, and examples thereof include an amine-based light stabilizer, a phenol-based light stabilizer, a phosphorus-based light stabilizer, and a thioether-based light stabilizer.
- an amine-based light stabilizer, Phenolic light stabilizers and phosphorus light stabilizers are preferable, and amine light stabilizers are more preferable in consideration of less yellowing and the like.
- These light stabilizers may be used alone or in combination of two or more. It is also possible to use a polymer incorporating these compounds.
- amine-based light stabilizer examples include a polymer of dimethyl succinate and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol (Tinuvin (registered trademark) 622, manufactured by BASF), Kohaku. Polymers of dimethyl acid and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol and N, N', N'', N''-tetrakis- (4,6-bis- (4,6-bis-) One-to-one with butyl- (N-methyl-2,2,6,6-tetramethylpiperidine-4-yl) amino) -triazine-2-yl) -4,7-diazadecan-1,10-diamine Reaction product (Tinuvin® 119, manufactured by BASF), dibutylamine 1,3-triazine N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl-1,6) -Hexamethylenediamine and N- (2,2,6,6-
- phenolic photostabilizer examples include 2,6-di-tertiary butyl-4-methylphenol, 4-hydroxymethyl-2,6-di-tertiary butylphenol, and 2,6-di-third.
- Grade Butyl-4-ethylphenol Butylated hydroxyanisole, n-octadecyl-3- (4-hydroxy-3,5-di-tertiary butylphenyl) propionate, distearyl- (4-hydroxy-3-methyl-) 5-Primary Butyl) benzylmalonate, tocopherol, 2,2'-methylenebis (4-methyl-6-tertiary butylphenol), 2,2'-methylenebis (4-ethyl-6-tertiary butylphenol) , 4,4'-methylenebis (2,6-di-tertiary butylphenol), 4,4'-butylidenebis (6-tertiary butyl-m-cresol), 4,4'-thiobis (6-third)
- Examples of the phosphorus-based photostabilizer include trisnonylphenyl phosphite, tris (2,4-di-tertiary butylphenyl) phosphite, and tris [2-tertiary butyl-4- (3-third).
- Phenylphosphite Tridecylphosphite, Octyldiphenylphosphite, Di (decyl) monophenylphosphite, Di (tridecyl) pentaerythritol diphosphite, Distealyl pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol diphosphite, bis (2,4-di-tertiary butylphenyl) pentaerythritol diphosphite, bis (2,6-di-third) Butyl-4-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tri-tertiary butylphenyl) pentaerythritol diphosphite, tetra
- thioether-based light stabilizer examples include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl, and distearyl; ⁇ -alkyl mercaptopropionic acid of a polyol such as tetrakis [methylene (3-dodecylthio) propionate] methane. Examples include ester compounds.
- additives include, for example, leveling agents, silane coupling agents, defoaming agents, thickeners, antistatic agents, infrared absorbers, foaming agents, inorganic fine particles, organic fine particles, dyes, pigments, antioxidants, etc. Examples thereof include anti-yellowing agents, brewing agents, anti-foaming agents, anti-settling agents, and adhesion-imparting agents.
- the Martens hardness of the primer layer at 23 ° C. is preferably 50 to 300 N / mm 2 , more preferably 100 to 250 N / mm 2, and even more preferably 150 to 200 N / mm 2 .
- the Martens hardness is at least the above lower limit value, the adhesion with the upper layer is improved, and when it is at least the above upper limit value, the adhesion with the lower layer tends to be improved.
- the method for measuring the Martens hardness is as described in Examples described later.
- the Martens hardness of the primer layer can be adjusted by the type of resin component constituting the primer layer, the crosslink density, and the like.
- the contact angle of 1 ⁇ L of distilled water at 23 ° C. on the surface of the primer layer is preferably 100 ° or less, more preferably 95 ° or less, still more preferably 90 ° or less.
- the lower limit of the contact angle of water is not particularly limited, but is preferably 1 ° or more. The method for measuring the contact angle of water is as described in Examples described later.
- the contact angle of water can be adjusted by the amount of the leveling agent added, the content of the raw material having a hydrophilic group (hydroxyl group, amino group, sulfonyl group, carboxyl group, salts thereof, etc.) and the like. Specifically, if the amount of the leveling agent added is reduced, the leveling agent is changed to a leveling agent having a low surface tension lowering ability, or the content of the raw material having a hydrophilic group is increased, the contact angle of water tends to be reduced.
- the thickness of the primer layer is preferably 0.01 to 30 ⁇ m, more preferably 0.5 to 20 ⁇ m, still more preferably 1 to 20 ⁇ m.
- the thickness of the primer layer is at least the above lower limit value, the adhesion between the substrate and the cured layer is more excellent, and when it is at least the above upper limit value, the appearance tends to be better.
- a primer layer is formed on a substrate (primer layer forming step), and a copolymer (A) and at least one silane compound (b) or a portion thereof are formed on the primer layer. It can be produced by applying a curable composition containing a component (B) composed of a hydrolyzed condensate and curing the composition to form a cured layer (cured layer forming step).
- Primer layer forming process examples include a method in which a primer containing a resin component and a diluent is applied onto a substrate and the diluent is removed by drying.
- the primer preferably contains at least one selected from the group consisting of UV absorbers and light stabilizers. If necessary, the primer may contain additives other than the ultraviolet absorber and the light stabilizer as long as the effects of the present invention are not impaired.
- the resin component, ultraviolet absorber, light stabilizer, and other additives are as described above.
- Examples of the diluent include water, an organic solvent and the like.
- Examples of the organic solvent include alcohol-based solvents, glycol-based solvents, hydrocarbon-based solvents, ester-based solvents, ketone-based solvents, ether-based solvents and the like.
- Examples of the alcohol solvent include methanol, ethanol, isopropyl alcohol, nbutanol, isobutanol, octanol, n-propyl alcohol, acetylacetone alcohol and the like.
- Glycol-based solvents include ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol mono n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene.
- examples thereof include glycol monoethyl ether, propylene glycol monobutyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate.
- hydrocarbon solvent examples include benzene, kerosene, toluene, xylene and the like.
- ester solvent examples include methyl acetate, ethyl acetate, butyl acetate, methyl acetoacetate, ethyl acetoacetate and the like.
- ketone solvent examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone and the like.
- ether solvent examples include ethyl ether, butyl ether, methyl cellosolve, ethyl cellosolve, dioxane, furan, tetrahydrofuran and the like.
- the organic solvent may be used alone or in combination of two or more.
- the content of the resin component is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, even if it is 100% by mass, based on 100% by mass of the non-volatile component of the primer. good.
- the content of the ultraviolet absorber varies depending on the type of the ultraviolet absorber, but is preferably 30% by mass or less, more preferably 0.01 to 20% by mass, and further preferably 0 with respect to 100% by mass of the non-volatile component of the primer. It is in the range of 1 to 15% by mass, particularly preferably 0.3 to 15% by mass.
- the content of the light stabilizer varies depending on the type of the light stabilizer, but is preferably 30% by mass or less, more preferably 0.01 to 20% by mass, and further preferably 0 with respect to 100% by mass of the non-volatile component of the primer. It is in the range of 1 to 15% by mass, particularly preferably 0.3 to 15% by mass.
- the concentration of the non-volatile component with respect to the entire primer is not particularly limited, but is preferably in the range of 80% by mass or less, more preferably 0.1 to 70% by mass, still more preferably 10 to 70%, and particularly preferably 20 to 60%. be. By using it in the above range, a curable composition having excellent coatability can be obtained.
- Primers can be prepared by mixing resin components, diluents, UV absorbers, light stabilizers, and other additives as needed.
- the coating method known methods such as brush coating, gravure coater method, die coater method, bar coater method, spray coating method, flow coating method, dip coating method, spin coating method and curtain coating method can be used. ..
- the curing method include the same methods as described above, and a method of irradiating the curable composition with active energy rays is preferable.
- the curable composition contains a diluent
- for drying to remove the diluent after coating the substrate with the curable composition and before irradiating the curable composition with active energy rays. It may be heat-treated.
- the heat treatment for drying can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the cured product layer obtained by irradiating the cured product layer with active energy rays after the heat treatment has a long-term outdoor adhesion as compared with the one without the heat treatment because the diluent is less likely to remain inside the cured product layer.
- the drying conditions are preferably 40 to 90 ° C., more preferably 50 to 70 ° C., and preferably 60 to 180 seconds, preferably 90 to 150 seconds as the drying time from the viewpoint of the appearance and adhesion of the cured product layer. Is more preferable.
- the curable composition may be heat-treated after being irradiated with active energy rays.
- This heat treatment can be performed by irradiation with a near-infrared lamp, circulation of warm air, or the like.
- the cured product layer obtained by heat treatment after curing by irradiation with active energy rays tends to have excellent hardness and durability because the condensation reaction rate is higher than that without heat treatment.
- the sliding angle of water at 23 ° C. and 20 ⁇ L on the surface of the cured product layer (initial cured product layer) formed as described above is preferably as low as possible, preferably 60 ° or less, more preferably 50 ° or less. 40 ° or less is more preferable, 30 ° or less is particularly preferable, and 20 ° or less is most preferable.
- the lower limit of the sliding angle of water There is no particular limitation on the lower limit of the sliding angle of water, and it is 0 ° or more. If the sliding angle of water is not more than the above upper limit, raindrops and snow adhering to the surface can easily slide down.
- the sliding angle of water after the durability test is particularly important in a wide range of application development, and a lower one is preferable, and a smaller change from the initial stage is preferable.
- the surface of the cured product layer (cured product layer after the durability test) after the cured product layer is formed as described above and a durability test is performed at 50 ° C. and 99% RH or higher for 96 hours.
- the sliding angle of 20 ⁇ L of water at 23 ° C. is preferably 60 ° or less, more preferably 50 ° or less, further preferably 40 ° or less, particularly preferably 30 ° or less, and most preferably 20 ° or less.
- There is no particular limitation on the lower limit of the sliding angle of water for example, 1 ° or more.
- the amount of change in the water slide angle of the cured product layer after the durability test from the water slide angle of the initial cured product layer is preferably 40 ° or less, more preferably 30 ° or less, further preferably 20 ° or less, and most preferably 15 ° or less. There is no particular lower limit, but it is preferably 0 °. Within this range, the same level of performance as in the initial stage can be exhibited over a long period of time, and product design becomes easier.
- the cured product layer is composed of a cured product of the resin composition containing the copolymer (A) and the component (B), it is excellent in appearance, water permeability and durability.
- This laminated body is used for sensing members such as members through which electromagnetic waves of sensing members (millimeter wave radar, LiDAR, etc.) pass; various automobile lamp lenses (vehicle lamps), resin glazing, road signs, traffic signals, camera lenses, etc. It can be used for 5G-related members, antennas, solar panels, window glass, resin glass, automobile glass and the like. Among the above, the sensing member is most suitable for the use of the laminated body.
- ⁇ Appearance> The appearance of the evaluation sample was visually evaluated.
- the judgment criteria are as follows. (criterion) A: A transparent and smooth coating film is formed without any abnormalities such as whitening, cracks and blisters. B: There are slight abnormalities such as whitening, cracks, and blisters. C: Abnormalities such as whitening, cracks, and blisters are observed.
- ⁇ Water smoothness> With respect to the cured film surface of the evaluation sample, the sliding angle of water at 23 ° C. and 20 ⁇ L was measured by tilting the substrate by the intermittent tilting method, and the slipperiness was evaluated. Specifically, a contact angle meter (DM-500, manufactured by Kyowa Interface Science) was used on the cured film surface of the evaluation sample horizontally placed on the sample fixing table in an environment of 23 ° C. and 50% RH. After dropping a droplet of 20 ⁇ L of distilled water, the evaluation sample was intermittently tilted by 1 °, and the tilt angle when the droplet started to slide was taken as the slide angle.
- the criteria for determining water smoothness are as follows.
- the primer layer to be used for measuring the Martens hardness was prepared under the following conditions. (Method of making test pieces) Base material: Polycarbonate plate (PC, 3 mm thick), Coating: Spray coating, Dry film thickness: 13 ⁇ m, Curing conditions: High-pressure mercury lamp 2000 mJ / cm 2 when the primer is active energy ray curable, 120 ° C x 30 minutes when the primer is thermosetting. The Martens hardness value changes depending on the type and film thickness of the base material.
- ⁇ Contact angle> The contact angle of water was measured by the sessile drop method. Specifically, in an environment of 23 ° C. and 50% RH, a contact angle meter (DM-500, Kyowa) was placed on the surface of the cured layer (or the surface of the primer layer before forming the cured layer) of the evaluation sample placed horizontally. 1 ⁇ L of distilled water was added dropwise using (manufactured by Kyowa Interface Science), and the contact angle (static contact angle) was measured 5 seconds after the addition.
- DM-500 DM-500, Kyowa
- the adhesiveness of the cured layer was evaluated by peeling the cellophane tape. Specifically, in an environment of 23 ° C. and 50% RH, cellophane tape was crimped to the surface of the cured layer of the evaluation sample with a finger, quickly peeled off in the direction of 45 ° diagonally toward you, and the area of the cured layer that was visually peeled off (the area of the cured layer was visually removed. The peeling area) was confirmed, and the adhesiveness was evaluated.
- the evaluation criteria for adhesion are as follows. A: No peeling. B: Peeling is observed, but the peeling area is less than 50% of the crimping area of the cellophane tape. C: The peeled area is 50% or more of the crimping area of the cellophane tape.
- ⁇ Durability> For the cured film of the evaluation sample, a wetness tester (device name: wetness tester, model CT-3H, manufactured by Suga Test Instruments Co., Ltd.) was used, and the temperature inside the tank was 50 ° C. and the humidity inside the tank was 99% RH or more. A 96-hour durability test was carried out under the conditions. After the durability test, the above-mentioned appearance and water-sliding property were evaluated.
- ⁇ Weather resistance> For the weather resistance test, a weather resistance tester (device name: Super Xenon Weather Meter, model SX75, manufactured by Suga Test Instruments Co., Ltd.) was used for 12 minutes of rainfall in 60 minutes and an irradiation intensity of 180 W / m 2 (300). A weather resistance test was carried out for 500 hours under the conditions of ( ⁇ 400 nm), a black panel temperature of 63 ° C., a tank temperature of 50 ° C., and a tank humidity of 50%. The evaluation sample was arranged so that the laminated cured film surface and the light source side of the weathering resistance tester were perpendicular to each other.
- KBM-5103 "KBM-5103" manufactured by Shin-Etsu Chemical Co., Ltd. (3-acryloxypropyltrimethoxysilane, 100% non-volatile component).
- FM-0721 "Silaplane FM-0721” manufactured by JNC Corporation (polydimethylsiloxane having a methacryloyl group at one end, Mw4200, 100% non-volatile component).
- FM-0711 "Silaplane FM-0711” manufactured by JNC Corporation (polydimethylsiloxane having a methacryloyl group at one end, Mw900, 100% non-volatile component).
- the structures of FM-0721 and FM-0711 are as follows.
- CH 2 C (CH 3 ) -COO-C 3 H 6- (Si (CH 3 ) 2 O) n- (CH 2 ) 3 CH 3
- Copolymer (E-2): The copolymer (FM-0721: KBM-5) obtained in Synthesis Example 6 described later. 103 20:30 (mass ratio), Mw53300).
- Component (B-1) Alkoxysilane hydrolyzed condensate (Mw1000) obtained in Synthesis Example 7 described later.
- Component (B-2) Alkoxysilane hydrolyzed condensate (Mw1600) obtained in Synthesis Example 8 described later.
- MS51 "MS51” manufactured by Mitsubishi Chemical Corporation (tetramethoxysilane partial hydrolysis condensate, Mw 800 to 1100, 100% non-volatile component).
- Photoacid generator "CPI-200K” manufactured by San-Apro (p-phenylthiophenyldiphenylsulfonium hexafluorophosphate, 50% non-volatile component).
- IPA 2-propanol.
- PGM Propylene glucol monomethyl ether.
- Perocta O “Perocta O” manufactured by NOF CORPORATION (2-ethylhexaneperoxyate 1,1,3,3-tetramethylbutyl).
- copolymers (A-1) to (A-4) correspond to the copolymer (A), and the copolymers (E-1) and (E-2) are copolymers. This is a comparative product that does not fall under (A).
- the product obtained was a polymer having a non-volatile component of 30% and a weight average molecular weight (Mw) of 16200.
- the product obtained was a polymer having a non-volatile component of 30% and a weight average molecular weight (Mw) of 19,800.
- the flask was set in an oil bath, stirring was started under a nitrogen atmosphere, and the temperature was raised until the internal temperature reached 85 ° C. Thirty minutes after the internal temperature reached 85 ° C., the monomer mixture was added dropwise from the dropping funnel over 2 hours and held for 1 hour, then 0.21 g of Perocta O was added, and 1 hour later, further Per Octa O was added. 0.21 g was added, the reaction was carried out for 5 hours, and then the mixture was cooled.
- the product obtained was a polymer having a non-volatile component of 30% and a weight average molecular weight (Mw) of 15500.
- the monomer mixture was added dropwise from the dropping funnel over 2 hours and held for 1 hour, then 0.20 g of Perocta O was added, and 1 hour later, the Per Octa O was further added. 0.20 g was added, the reaction was carried out for 5 hours, and then the mixture was cooled.
- the product obtained was a polymer having a non-volatile content of 30% and a weight average molecular weight (Mw) of 23400.
- Example 1 ⁇ Preparation of resin composition> 3.5 parts of the copolymer (A-1), 4.2 parts of the component (B-1), 10 parts of the IPA, 10 parts of the PGM, and the photoacid generator CPI-200K (Sun Appro). A resin composition was prepared by mixing with 0.04 part of (manufactured by).
- the obtained resin composition was applied to the surface of a polycarbonate resin plate (PC plate) having a thickness of 3 mm (manufactured by Mitsubishi Engineering Plastics Co., Ltd., trade name: "IUPILON ML-300"), and the thickness after drying was 0.7 ⁇ m.
- the coating film was dried (solvent volatilized) by heating for 120 seconds in a hot air dryer preheated to 60 ° C.
- the dried coating film was subjected to 1000 mJ / cm 2 (integrated irradiation amount at a wavelength of 340 to 380 nm) using a high-pressure mercury lamp (USX5-0902, manufactured by Igraphic) in an air atmosphere.
- the coating film was cured by irradiating with ultraviolet rays (measured using (manufactured by ORC Manufacturing Co., Ltd.)) to obtain an evaluation sample in which a cured film of a resin composition was laminated on a PC plate.
- Examples 2 to 7, Comparative Examples 1 to 5, Reference Example 1 The composition was prepared in the same manner as in Example 1 except that the types and amounts (parts) of the components to be blended in the composition were as shown in Tables 1 and 2, and evaluation samples were prepared. The evaluation results of the composition and the evaluation sample are shown in Tables 1 and 2. However, in Comparative Example 5, the compatibility of the composition in the liquid state was low and it could not be molded as a cured film, so that the evaluation sample was not prepared and evaluated.
- Example 8 to 10 The composition was prepared in the same manner as in Example 1 except that the types and amounts (parts) of the components to be blended in the composition were as shown in Table 1. Using this composition, an evaluation sample was prepared in the same manner as in Example 1 except that the base material was changed from a PC plate to a glass plate having a thickness of 5 mm. The evaluation results of the composition and the evaluation sample are shown in Table 1.
- ⁇ Preparation of primer> In a resin obtained by mixing 22 parts of a caprolactone modified product of dipentaerythritol hexaacrylate (DPHA) (“DPCA-20” manufactured by Nippon Kayaku Co., Ltd.) and 16 parts of urethane acrylate, 0.9 part of benzophenone as a photopolymerization initiator was added. After adding 3 parts of tinubin 400 (manufactured by BASF) as an ultraviolet absorber and 0.15 parts of tinubin 123 (manufactured by BASF) as a light stabilizer, propylene glycol monomethyl ether is used to make the non-volatile component 32% by mass.
- DPHA dipentaerythritol hexaacrylate
- an active energy ray-curable primer (1) Diluted to prepare an active energy ray-curable primer (1).
- the urethane acrylate was prepared as follows. In a flask equipped with a dropping funnel with a heat retaining function, a reflux condenser, a stirring blade and a temperature sensor, 530 g (2 mol) of dicyclohexylmethane diisocyanate and 300 ppm of din-butyl tin dilaurate were charged and heated to 40 ° C. Then, 800 g (weight average molecular weight 800) of polycarbonate diol (trade name: Kuraray polyol C-770, manufactured by Kuraray Co., Ltd.) as a polyol compound was added dropwise over 4 hours. After stirring at 40 ° C.
- polycarbonate diol trade name: Kuraray polyol C-770, manufactured by Kuraray Co., Ltd.
- the product obtained was a polymer having a non-volatile component of 75% and a molecular weight of 1500.
- the above primer (1) was spray-coated on a 3 mm-thick polycarbonate resin plate (PC plate) (manufactured by Mitsubishi Engineering Plastics, trade name: "IUPILON ML-300") and then preheated to 70 ° C.
- the coating film was dried (solvent volatilized) by heating in a hot air dryer for 90 seconds.
- the dried coating film was measured in an air atmosphere using a high-pressure mercury lamp at 2000 mJ / cm 2 (integrated irradiation dose at a wavelength of 340 to 380 nm was measured using an ultraviolet photometer UV-351 (manufactured by ORC Manufacturing Co., Ltd.).
- the curable composition is spray-coated on the primer layer so that the thickness after drying is 700 nm, and then heated in a hot air dryer preheated to 60 ° C. for 120 seconds to form a coating film. It was dried (the solvent was volatilized).
- the dried coating film was subjected to 1000 mJ / cm 2 (integrated irradiation amount at a wavelength of 340 to 380 nm) using a high-pressure mercury lamp (USX5-0902, manufactured by Igraphic) in an air atmosphere, with an ultraviolet photometer UV-351.
- the coating film was cured by irradiating with ultraviolet rays (measured using (manufactured by ORC Manufacturing Co., Ltd.)). As a result, a laminated body in which a primer layer and a cured layer were sequentially laminated on a PC plate was obtained.
- Examples 12, 13, 16 and Comparative Examples 6 to 9 The composition was prepared in the same manner as in Example 11 except that the types and amounts (parts) of the components to be blended in the composition were as shown in Tables 3 and 4, and evaluation samples were prepared. The evaluation results of the composition and the evaluation sample are shown in Tables 3 and 4.
- Example 14 100 parts of Basonol (registered trademark) HPE1170B (manufactured by BASF) as a polyol, 30 parts of Kuraray polyol C-1090 (manufactured by Kuraray), 159 parts of Duranate MHG-80B as an isocyanate (manufactured by Asahi Kasei Co., Ltd.), MEK as inorganic fine particles.
- Basonol registered trademark
- HPE1170B manufactured by BASF
- Kuraray polyol C-1090 manufactured by Kuraray
- Duranate MHG-80B as an isocyanate
- MEK as inorganic fine particles.
- thermosetting primer (2) (manufactured by Nissan Chemical Co., Ltd.) 70 parts, Chinubin 405 (manufactured by BASF) as an ultraviolet absorber 30 parts, Chinubin 152 (manufactured by BASF) as a light stabilizer 0.5 parts, as a curing acceleration catalyst 0.05 parts of dibutyltin dilaurate (DBTDL) was uniformly mixed, and further diluted with cyclohexanone and MIBK so that the concentration of the non-volatile component was about 32% to prepare a thermosetting primer (2). ..
- DBTDL dibutyltin dilaurate
- the primer (2) When forming the primer layer, the primer (2) was spray-coated so that the thickness of the coating film after curing was 10 ⁇ m, and the cured film (primer layer) was formed by heat-treating at 120 ° C. for 30 minutes. Prepared an evaluation sample in the same manner as in Example 11. The evaluation results are shown in Table 3.
- Example 15 16 parts of BR-83 (manufactured by Mitsubishi Chemical Co., Ltd.) as a non-curable acrylic resin, 2.2 parts of tinubin PS (manufactured by BASF) as an ultraviolet absorber, and 1 part of tinubin 123 (manufactured by BASF) as a light stabilizer. .8 parts were diluted with PGM and methyl ethyl ketone (MEK) so that the concentration of the non-volatile component was 16%, and mixed uniformly to prepare the primer (3). When forming the primer layer, the primer (3) is spray-coated so that the thickness of the coating film after drying becomes 10 ⁇ m, and heat-treated at 90 ° C. for 30 minutes to form a non-curable coating film (primer layer). An evaluation sample was prepared in the same manner as in Example 11 except that the above was formed. The evaluation results are shown in Table 3.
- Example 17 When a 100 ⁇ m-thick polycarbonate film (PC film, FE-2000 manufactured by Mitsubishi Engineering Plastics) was used instead of the PC plate to form the primer layer and the cured layer, the primer (1) and the above-mentioned primer (1) were applied on the above-mentioned PC film.
- An evaluation sample was prepared in the same manner as in Example 11 except that the resin composition described in Example 12 was coated with a bar coater so that the thickness after drying was 10 ⁇ m and 700 nm, respectively. The evaluation results are shown in Table 3.
- Example 18 When a polyethylene terephthalate film (PET film, Mitsubishi Chemical Diafoil T600E50 W07) having a thickness of 50 ⁇ m was used instead of the PC plate to form the primer layer and the cured layer, the primer (1) and the above-mentioned primer (1) were applied on the PET film.
- An evaluation sample was prepared in the same manner as in Example 11 except that the resin composition described in Example 12 was coated with a bar coater so that the thickness after drying was 10 ⁇ m and 700 nm, respectively. The evaluation results are shown in Table 3.
- a curable composition was prepared by mixing 3.5 parts of the copolymer (A-1), 4.2 parts of the component (B-1), 10 parts of IPA, and 10 parts of PGM. ..
- a curable composition is spray-coated on a glass plate having a thickness of 5 mm so that the thickness after curing is 0.7 ⁇ m, and the glass plate is cured by heating in a hot air dryer at 150 ° C. for 1 hour. An evaluation sample in which a cured film was laminated was obtained.
- Example 20 and 21 Comparative Examples 10 to 13
- a curable composition was prepared and an evaluation sample was prepared in the same manner as in Example 19 except that the types and amounts (parts) of the components to be blended in the curable composition were as shown in Table 5.
- the evaluation results of the evaluation sample are shown in Table 5.
- Comparative Example 13 a cured film could not be formed, so evaluation was not performed.
- Example 22 A curable composition was prepared in the same manner as in Example 1 except that the types and amounts (parts) of the components to be blended in the curable composition were as shown in Table 5.
- the obtained curable composition was spray-coated on a glass plate having a thickness of 5 mm so as to have a thickness of 0.7 ⁇ m after curing, and then 120 in a hot air dryer preheated to 60 ° C.
- the coating film was dried (solvent volatilized) by heating for seconds.
- the dried coating film was subjected to 1000 mJ / cm 2 (integrated irradiation amount at a wavelength of 340 to 380 nm) using a high-pressure mercury lamp (USX5-0902, manufactured by Igraphic) in an air atmosphere, with an ultraviolet photometer UV-351.
- the coating film was cured by irradiating with ultraviolet rays (measured using (manufactured by ORC Manufacturing Co., Ltd.)) to obtain a laminated body in which a cured film was laminated on a glass plate.
- the evaluation results of the evaluation sample are shown in Table 5.
- each component is the amount including volatile matter.
- An “x” in the evaluation of "water-sliding” means that the droplets did not move on the surface of the cured film even when the inclination angle was changed to 90 °, and the sliding angle could not be measured.
- “-” Means that the surface of the cured film was hydrophilic, so that droplets were not formed and the sliding angle could not be measured.
- N / A means that the measurement could not be performed due to the influence of the surface condition of the coating film and the like.
- the cured products of the compositions of Examples 1 to 10 were excellent in appearance and water smoothness both in the initial stage and after the durability test.
- the composition of Comparative Example 1 did not contain a copolymer that imparts water-sliding property, and the surface of the cured film was hydrophilic, so that it was impossible to determine the water-sliding property as shown in Table 2.
- the composition of Comparative Example 2 did not contain the component (B), the appearance of the cured film was low as shown in Table 2. In addition, the hardness of the cured film was low.
- Comparative Example 3 used a copolymer containing no polydimethylsiloxane unit, which is a component that imparts water smoothness, the water smoothness was low as shown in Table 2.
- Comparative Example 4 used a copolymer having a low content of polydimethylsiloxane unit, which is a component that imparts water smoothness, the water smoothness was low as shown in Table 2.
- Comparative Example 5 was added as a monomer without copolymerizing the constituent components of the copolymer (A-1), the compatibility in the liquid state was low, and as shown in Table 2, it was cured. It could not be molded as a film.
- the laminates of Examples 11 to 18 were excellent in adhesion between the base material and the cured layer, appearance of the cured layer, water slipperiness, hardness and hardness. Further, in Examples 11 to 14 and 16 to 18, the appearance and water permeability of the cured layer after the durability test were also good, and the durability was excellent. On the other hand, since the laminated body of Comparative Example 6 did not have the component (B), the appearance was low as shown in Table 4. In addition, the curability was also poor, the strength of the coating film was poor, and the film did not function as a cured film. Since the laminate of Comparative Example 7 did not have the copolymer (A), it was inferior in water-sliding property as shown in Table 4.
- the cured films of Examples 19 to 22 were excellent in appearance and water smoothness at the initial stage and after the weather resistance test.
- the cured film of Comparative Example 10 did not contain a copolymer that imparts water-sliding property, and the surface of the cured film was hydrophilic, so that it was impossible to determine the water-sliding property as shown in Table 5.
- the cured film of Comparative Example 11 did not contain the component (B), the appearance was low as shown in Table 5.
- the curability was also poor, the strength of the coating film was poor, and the film did not function as a cured film.
- Comparative Example 12 As the cured film of Comparative Example 12 used a copolymer containing no polyalkylsiloxane unit which is a component for imparting water smoothness, the water smoothness was low as shown in Table 5. In Comparative Example 13, since the constituent components of the copolymer (A-1) were added to the curable composition as a monomer without copolymerization, the compatibility in the liquid state was low as shown in Table 5. , Can not be molded as a cured film.
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Abstract
Description
本願は、2020年9月11日に、日本に出願された特願2020-153163号、並びに2020年11月30日に、日本に出願された特願2020-198572号、特願2020-199028号及び特願2020-199037号に基づき優先権を主張し、その内容をここに援用する。
また、近年では、各種部品の小型化に伴い、耐久性に優れる透過性ガラスがカバー部材に用いられることも増えてきた。
上記センサー装置は、意匠性との両立から、車輌前面のエンブレムやフロントグリルの裏側に配置されることが多い。しかし、電磁波は雨滴や雪による減衰や散乱を受けやすく、電磁波が通過するエンブレムやフロントグリル等の最表面に雨滴や雪が付着すると、対象物との距離の測量に支障をきたす問題がある。そこで、エンブレムやフロントグリルの表面部材には水滴を容易に滑落させることができる滑水性という機能が求められる。
[1] ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)とを含み、
前記共重合体(A)を構成する全構成単位の合計質量に対し、前記シリコーンマクロモノマー(X)に基づく構成単位の割合と前記単量体(Y)に基づく構成単位の割合の合計が55質量%以上である、樹脂組成物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
[2] 前記成分(B)が、少なくとも1種の下記式(b)で表されるシラン化合物又はその部分加水分解縮合物からなる、[1]に記載の樹脂組成物。
R4 4-nSi(OR5)n ・・・(b)
ただし、R4は水素原子、アルキル基、アリール基又はアラルキル基を表し、R5はアルキル基又はフェニル基を表し、nは2~4の整数を表し、n個のOR5は互いに異なっていてもよく、nが2の場合、(4-n)個のR4は互いに異なっていてもよい。
[3] 前記シリコーンマクロモノマー(X)の重量平均分子量が500~40000である、[1]又は[2]に記載の樹脂組成物。
[4] 前記共重合体(A)を構成する全構成単位の合計質量に対し、前記シリコーンマクロモノマー(X)に基づく構成単位の割合が15~60質量%であり、前記単量体(Y)に基づく構成単位の割合が40~85質量%である、[1]~[3]のいずれかに記載の樹脂組成物。
[5] 前記共重合体(A)の重量平均分子量が3000~400000である、[1]~[4]のいずれかに記載の樹脂組成物。
[6] 前記成分(B)の重量平均分子量が500以上である、[1]~[5]のいずれかに記載の樹脂組成物。
[7] 前記成分(B)がテトラアルコキシシランの部分加水分解縮合物である、[1]~[6]のいずれかに記載の樹脂組成物。
[8] 前記成分(B)が、少なくとも1種の前記シラン化合物の部分加水分解縮合物であって重量平均分子量が300~3000である部分加水分解縮合物を、さらに触媒の存在下に加水分解縮合反応させた二次反応物である、[1]~[7]のいずれかに記載の樹脂組成物。
[9] さらに開始剤(C)を含む、[1]~[8]のいずれかに記載の樹脂組成物。
[10] 前記開始剤(C)が光重合開始剤である、[9]に記載の樹脂組成物。
[11] 前記開始剤(C)が、光酸発生剤及び光塩基発生剤からなる群から選ばれる少なくとも1種を含む、[9]又は[10]に記載の樹脂組成物。
[12] センシング部材用途に用いられる、[1]~[11]のいずれかに記載の樹脂組成物。
[13] [1]~[12]のいずれかに記載の樹脂組成物の硬化物。
[14] ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)を含み、
槽内温度50℃、槽内湿度99%RH以上の条件にて96時間の耐久性試験を実施した後に、傾斜角を1°ずつ断続的に変化させる断続傾斜により基材を傾けて測定される23℃、20μLの蒸留水の滑落角が60°以下である表面を有する、硬化物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
[15] 基材と、[14]に記載の硬化物からなる層を有する積層体。
[16] 基材の上に設けられたプライマー層と、前記プライマー層の上に設けられた[14]に記載の硬化物からなる層とを有する積層体。
[17] ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)と、光重合開始剤とを含む、樹脂組成物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
[18] ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)と、光重合開始剤とを含む、硬化物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
[19] ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物を含む成分(B)とを含む樹脂組成物を、加熱処理又は活性エネルギー線照射により硬化させる、硬化物の製造方法。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
なお、本明細書において「~」という表現を用いる場合、その前後の数値又は物性値を含む表現として用いるものとする。また、本発明において、「(メタ)アクリル」という表現を用いた場合、「アクリル」と「メタクリル」の一方又は両方を意味するものとする。「(メタ)アクリレート」、「(メタ)アクリロイル」等についても同様である。
本発明の一態様に係る樹脂組成物(以下、「本樹脂組成物」とも記す。)は、ポリジメチルシロキサンユニットを含む共重合体(A)と、少なくとも1種の特定のシラン化合物又はその部分加水分解縮合物からなる成分(B)とを含む。
本樹脂組成物は、必要に応じて、開始剤(C)及び希釈剤をさらに含んでいてもよい。
本樹脂組成物は、必要に応じて、上記以外の他の成分をさらに含んでいてもよい。
共重合体(A)は、ポリアルキルシロキサンユニットを含む。ポリアルキルシロキサンユニットを含む共重合体(A)を含むことで、本樹脂組成物の硬化物が滑水性を示す。
ポリアルキルシロキサンユニットは、2以上のアルキルシロキサン単位を含む。ポリアルキルシロキサンユニットとしては、例えば直鎖型、分岐型、デンドリマー型があり、その中でも-(Si(R18)2O)n-で表される直鎖型のポリアルキルシロキサンユニットを含むことが好ましい。R18は炭素数1~10の炭化水素基を表し、炭素数1~5の炭化水素基が好ましく、メチル基がより好ましい。nはポリアルキルシロキサンユニットの平均重合度を示す。
ポリアルキルシロキサンユニットの平均重合度は、5~1000が好ましく、10~500がより好ましく、30~300がさらに好ましく、50~200が特に好ましい。平均重合度が上記下限値以上であれば、本樹脂組成物の硬化物の滑水性がより優れ、上記上限値以下であれば、ポリアルキルシロキサンユニットを有する単量体(後述するシリコーンマクロモノマー(X))が他の単量体と相溶しやすく、共重合体(A)を製造しやすい傾向がある。
共重合体(A)は、滑水性等の性能を向上させるという観点から、特定の式(1)で表される基を有する単量体(Y)に基づく構成単位(以下、「構成単位(Y)」とも記す。)をさらに含むことが好ましい。
共重合体(A)は、必要に応じて、性能を損なわない範囲で、マクロモノマー(X)及び単量体(Y)以外の単量体(Z)に基づく構成単位(以下、「構成単位(Z)」とも記す。)をさらに含んでいてもよい。
シリコーンマクロモノマー(X)としては、ポリアルキルシロキサンユニットと、重合性官能基とを含む化合物が挙げられる。
重合性官能基としては、重合性炭素-炭素二重結合等の重合性不飽和結合を含む基であればよく、例えば、(メタ)アクリロイル基、ビニル基、(メタ)アクリルアミド基等が挙げられる。これらの中でも、他の単量体との共重合のしやすさの観点から、(メタ)アクリロイル基が好ましい。
ポリアルキルシロキサンユニットと重合性官能基とは、連結基を介して結合していてもよい。連結基としては、例えば、炭素数1~6のアルキレン基等の炭化水素基が挙げられる。
CH2=CR19-CO-O-R20-(Si(R18)2O)n-R21 ・・・(2)
ただし、R18は炭素数1~10の炭化水素基を表し、nは平均重合度を表し、R19は水素原子又はメチル基を表し、R20は炭素数1~10の炭化水素基を表し、R21は水素原子、炭素数1~10の炭化水素基、又はアリール基を表す。
nの好ましい範囲は、前記したポリアルキルシロキサンユニットの平均重合度の好ましい範囲と同様である。
これらの中でも特に、R18は炭素数1~10の炭化水素基を表し、炭素数1~5の炭化水素基が好ましく、メチル基がより好ましく、R19はメチル基が好ましく、R20は炭素数1~6の炭化水素基が好ましく、炭素数2~4の炭化水素基がより好ましく、R21は炭素数1~6の炭化水素基が好ましく、炭素数1~4の炭化水素基がより好ましい。
シリコーンマクロモノマー(X)のMwは、ゲルパーミエーションクロマトグラフィ(GPC)により測定される標準ポリスチレン換算の値である。
シリコーンマクロモノマー(X)は、1種を単独で使用してもよいし2種以上を併用してもよい。
単量体(Y)は、下記式(1)で表される基(以下、「基(1)」とも記す。)を有する。単量体(Y)によって共重合体(A)に基(1)が導入されると、共重合体(A)中の基(1)と成分(B)とが反応し、ポリジメチルシロキサンユニットが本樹脂組成物の硬化物表面にブリードアウトすることを抑制でき、耐久性が向上する。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のR3は互いに異なっていてもよい。
R2及びR3のアルキル基、アルケニル基、アリール基はそれぞれ置換基を有していてもよい。置換基としては、例えば塩素原子等のハロゲン原子、メトキシ基、エトキシ基のアルコキシ基等が挙げられる。
R3のアシル基としては、例えば(メタ)アクリル基、アセチル基、アセトイミドイル基、アルデヒド基、チオアセチル基、プロピオニル基、ベンゼンスルホニル基、ベンゾイル基等が挙げられる。
上記のうち、汎用で活性が高く良好な硬化性が得られる点からは、トリメトキシシリル基、トリエトキシシリル基、ジメトキシメチルシリル基が好ましく、ジメトキシメチルシリル基がより好ましい。貯蔵安定性の点からは、ジメトキシメチルシリル基、トリエトキシシリル基が好ましい。特に高い硬化性を示す点からは、(クロロメチル)ジメトキシシリル基、(メトキシメチル)ジメトキシシリル基が好ましい。硬化物の復元性が高くなる傾向にある点では、トリメトキシシリル基、トリエトキシシリル基等の3官能性シリル基が好ましい。
重合性官能基としては、前記と同様のものが挙げられ、好ましい態様も同様である。
反応性基としては、例えば、ビニル基、(メタ)アクリロイル基、(メタ)アクリルアミド基、エポキシ基、環状エポキシ基、メルカプト基、アミノ基、ジアミノ基、酸無水物基、イソシアネート基等が挙げられる。
基(1)と重合性官能基又は反応性基とは、連結基を介して結合していてもよい。連結基としては、例えば、炭素数1~6のアルキレン基等の炭化水素基が挙げられる。
ただし、単量体(Y)はこれらに限定されるものではない。例えば、他の単量体と共重合できる重合性官能基又は重合体に対し付加できる基(1)以外の反応性基を有するチタネート系、アルミネート系又はジルコネート系のカップリング剤を用いてもよい。
単量体(Y)は、1種を単独で使用してもよいし2種以上を併用してもよい。
単量体(Z)としては、シリコーンマクロモノマー(X)と共重合可能であればよく、例えば、前記した重合性官能基を有する化合物(ただし、シリコーンマクロモノマー(X)及び単量体(Y)を除く。)が挙げられる。
(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸n-プロピル、(メタ)アクリル酸イソプロピル、(メタ)アクリル酸n-ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸tert-ブチル、(メタ)アクリル酸n-ペンチル、(メタ)アクリル酸n-ヘキシル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n-ヘプチル、(メタ)アクリル酸n-オクチル、(メタ)アクリル酸2-エチルヘキシル、(メタ)アクリル酸ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸フェニル、(メタ)アクリル酸トルイル、(メタ)アクリル酸ベンジル、(メタ)アクリル酸2-メトキシエチル、(メタ)アクリル酸3-メトキシブチル、(メタ)アクリル酸2-ヒドロキシエチル、(メタ)アクリル酸2-ヒドロキシプロピル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸グリシジル、(メタ)アクリル酸2-アミノエチル、(メタ)アクリル酸のエチレンオキサイド付加物、(メタ)アクリル酸トリフルオロメチルメチル、(メタ)アクリル酸2-トリフルオロメチルエチル、(メタ)アクリル酸2-パーフルオロエチルエチル、(メタ)アクリル酸2-パーフルオロエチル-2-パーフルオロブチルエチル、(メタ)アクリル酸パーフルオロエチル、(メタ)アクリル酸トリフルオロメチル、(メタ)アクリル酸ビス(トリフルオロメチル)メチル、(メタ)アクリル酸2-トリフルオロメチル-2-パーフルオロエチルエチル、(メタ)アクリル酸2-パーフルオロヘキシルエチル、(メタ)アクリル酸2-パーフルオロデシルエチル、(メタ)アクリル酸2-パーフルオロヘキサデシルエチル等の(メタ)アクリル酸系単量体。
(メタ)アクリルアミド、N-メチル(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N-エチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-n-プロピル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、N-ジメチルアミノエチル(メタ)アクリルアミド、N-ジメチルアミノプロピル(メタ)アクリルアミド、ジアセトン(メタ)アクリルアミド、N-(メタ)アクリロイルピペリジン、(メタ)アクロイルモルホリン等の(メタ)アクリルアミド系単量体。
無水マレイン酸、マレイン酸、マレイン酸のモノアルキルエステル及びジアルキルエステル;フマル酸、フマル酸のモノアルキルエステル及びジアルキルエステル。
マレイミド、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、ヘキシルマレイミド、オクチルマレイミド、ドデシルマレイミド、ステアリルマレイミド、フェニルマレイミド、シクロヘキシルマレイミド等のマレイミド系単量体。
アクリロニトリル、メタクリロニトリル等のニトリル基含有ビニル系単量体。
アクリルアミド、メタクリルアミド等のアミド基含有ビニル系単量体。
酢酸ビニル、プロピオン酸ビニル、ピバリン酸ビニル、安息香酸ビニル、桂皮酸ビニル等のビニルエステル類。
エチレン、プロピレン等のアルケン類。
ブタジエン、イソプレン等の共役ジエン類。
塩化ビニル、塩化ビニリデン、塩化アリル、アリルアルコール等。
単量体(Z)は、1種を単独で使用してもよいし2種以上を併用してもよい。
共重合体(A)を構成する全構成単位の合計質量に対する構成単位(X)の割合は、15~60質量%が好ましく、15~50質量%がより好ましく、20~50質量%がさらに好ましい。構成単位(X)の割合が上記下限値以上であれば、硬化物の滑水性がより良好になり、上記上限値以下であれば、未重合のシリコーンマクロモノマー(X)を少なくすることができるので、硬化物の透明性が良好になる傾向がある。
各構成単位の割合は、核磁気共鳴法や全反射測定法による赤外分光分析等の分析手法により求められる。
共重合体(A)のMwは、3000~400000が好ましく、5000~100000がより好ましく、7000~80000が特に好ましい。さらに8000~40000がより好ましい。共重合体(A)のMwが上記下限値以上であれば、共重合体(A)が硬化物内に強固に固定化されるので滑水性及び耐久性が向上する傾向があり、上記上限値以下であれば、本樹脂組成物において他の成分との相溶性が向上するので硬化物の外観が向上する傾向がある。
共重合体(A)のMwは、ゲルパーミエーションクロマトグラフィー(GPC)により測定される標準ポリスチレン換算の値である。
共重合体(A)の製造方法としては、特に限定されず、公知の方法を適宜採用できる。
例えば、構成単位(X)と構成単位(Y)とを有する共重合体は、以下の(i)又は(ii)の方法により製造できる。
(i)シリコーンマクロモノマー(X)、重合性官能基を含む単量体(Y)及び必要に応じて単量体(Z)を含む単量体混合物を重合する方法。
(ii)シリコーンマクロモノマー(X)及び必要に応じて単量体(Z)を含む単量体混合物を重合し、得られた重合体と、前記重合体に対し付加可能な反応性基を含む単量体(Y)とを反応させる方法。
特に滑水性を重視する用途においては、ケイ素原子を含有する化合物の含有割合をできる限り高くすることが好ましいため、構成単位(Z)を含有しないことが好ましい。
重合条件は、特に限定されないが、例えば30~180℃で0.5~24時間とすることができる。
重合開始剤としては、公知の各種の重合開始剤を用いることができる。例えば、2,2-アゾビス(4-メトキシ-2,4-ジメチルバレロニトリル)(V-70、富士フィルム和光純薬製)、2,2’-アゾビス(2,4-ジメチルバレロニトリル)(V-65、富士フィルム和光純薬製)2,2’-アゾビスイソブチロニトリル(V-60、富士フィルム和光純薬製)、2,2’-アゾビス(2-メチルブチロニトリル)(V-59、富士フィルム和光純薬製)等のアゾニトリル化合物;オクタノイルパーオキシド(パーロイル(登録商標)O、日油製)、ラウロイルパーオキシド(パーロイルL、日油製)、ステアロイルパーオキシド(パーロイルS、日油製)、スクシニックアシッドパーオキシド(パーロイルSA、日油製)、ベンゾイルパーオキサイド(ナイパー(登録商標)BW、日油製)、イソブチリルパーオキサイド(パーロイルIB、日油製)、2,4-ジクロロベンゾイルパーオキシド(ナイパーCS、日油製)、3,5,5-トリメチルヘキサノイルパーオキシド(パーロイル355、日油製)等のジアシルパーオキサイド;ジ-n-プロピルパーオキシジカーボネート(パーロイルNPP-50M、日油製)、ジイソプロピルパーオキシジカーボネート(パーロイルIPP-50、日油製)、ビス(4-t-ブチルシクロヘキシル)パーオキシジカーボネート(パーロイルTCP、日油製)、ジ-2-エトキシエチルパーオキシジカーボネート(パーロイルEEP、日油製)、ジ-2-エトキシヘキシルパーオキシジカーボネート(パーロイルOPP、日油製)、ジ-2-メトキシブチルパーオキシジカーボネート(パーロイルMBP、日油製)、ジ(3-メチル-3-メトキシブチル)パーオキシジカーボネート(パーロイルSOP、日油製)等のパーオキシジカーボネート;t-ブチルヒドロパーオキサイド(パーブチル(登録商標)H-69、日油製)、1,1,3,3-テトラメチルブチルヒドロパーオキサイド(パーオクタ(登録商標)H、日油製)、等のヒドロパーオキサイド;ジ-t-ブチルパーオキサイド(パーブチルD、日油製)、2,5-ジメチル-2,5-ビス(t-ブチルパーオキシ)ヘキサン(パーヘキサ(登録商標)25B、日油製)等のジアルキルパーオキサイド;α,α’-ビス(ネオデカノイルパーオキシ)ジイソプロピルベンゼン(ダイパー(登録商標)ND、日油製)、クミルパーオキシネオデカノエート(パークミル(登録商標)ND、日油製)、1,1,3,3-テトラメチルブチルパーオキシネオデカノエート(パーオクタND、日油製)、1-シクロヘキシル-1-メチルエチルパーオキシネオデカノエート(パーシクロ(登録商標)ND、日油製)、t-ヘキシルパーオキシネオデカノエート(パーヘキシル(登録商標)ND、日油製)、t-ブチルパーオキシネオデカノエート(パーブチルND、日油製)、t-ヘキシルパーオキシピバレート(パーヘキシルPV、日油製)、t-ブチルパーオキシピバレート(パーブチルPV、日油製)、1,1,3,3-テトラメチルブチルパーオキシ-2-エチルヘキサノエート(パーオクタO、日油製)2,5-ジメチル-2,5-ビス(2-エチルヘキサノイルパーオキシ)ヘキサン(パーヘキサ250、日油製)、1-シクロヘキシル-1-メチルエチルパーオキシ-2-エチルヘキサノエート(パーシクロO、日油製)、t-ヘキシルパーオキシ2-エチルヘキサノエート(パーヘキシルO、日油製)、t-ブチルパーオキシ2-エチルヘキサノエート(パーブチルO、日油製)、t-ブチルパーオキシイソブチレート(パーブチルIB、日油製)、t-ヘキシルパーオキシイソプロピルモノカーボネート(パーヘキシルI、日油製)、t-ブチルパーオキシマレイックアシッド(パーブチルMA、日油製)等のパーオキシエステル等の有機過酸化物が挙げられる。ただし、重合開始剤は特にこれらに限定されるものではない。
重合開始剤は、1種を単独で使用してもよいし2種以上を併用してもよい。
重合開始剤の使用量は、単量体混合物100質量部に対し、例えば0.01~10質量部である。
成分(B)は、少なくとも1種の下記式(b)で表されるシラン化合物(以下、「シラン化合物(b)」とも記す。)又はその部分加水分解縮合物からなる。
R4 4-nSi(OR5)n ・・・(b)
ただし、R4は水素原子、アルキル基、アリール基又はアラルキル基を表し、R5はアルキル基又はフェニル基を表し、nは2~4の整数を表し、n個のOR5は互いに異なっていてもよく、nが2の場合、(4-n)個のR4は互いに異なっていてもよい。
アリール基としては、フェニル基、トルイル基、ナフチル基等が挙げられる。
アラルキル基としては、ベンジル基、フェネチル基等が挙げられる。
Si(OR6)a(OR7)b(OR8)c(OR9)d ・・・(b1)
ただし、R6、R7、R8及びR9はそれぞれ独立に、アルキル基又はフェニル基を表す。a、b、c及びdは、0≦a≦4、0≦b≦4、0≦c≦4、0≦d≦4であって、且つa+b+c+d=4の条件を満たす整数である。
R6、R7、R8及びR9は上記R5と同様である。
R10Si(OR11)e(OR12)f(OR13)g ・・・(b2)
ただし、R10は水素原子、アルキル基、アリール基又はアラルキル基を表す。R11、R12及びR13はそれぞれ独立に、アルキル基又はフェニル基を表す。e、f、及びgは、0≦e≦3、0≦f≦3、0≦g≦3であって、且つe+f+g=3の条件を満たす整数である。
R10は上記R4と同様である。R11、R12及びR13は上記R5と同様である。
R14R15Si(OR16)h(OR17)i ・・・(b3)
ただし、R14及びR15はそれぞれ独立に水素原子、アルキル基、アリール基又はアラルキル基を表す。R16及びR17はそれぞれ独立にアルキル基又はフェニル基を表す。h及びiは、0≦h≦2、0≦i≦2であって、且つh+i=2の条件を満たす整数である。
R14及びR15は上記R4と同様である。R16及びR17は上記R5と同様である。
エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリプロポキシシラン、エチルトリペンチルオキシシラン、エチルトリフェニルオキシシラン、エチルモノメトキシジエトキシシラン、エチルモノメトキシジプロポキシシラン、エチルモノメトキシジペンチルオキシシラン、エチルモノメトキシジフェニルオキシシラン、エチルメトキシエトキシプロポキシシラン、及びエチルモノメトキシモノエトキシモノブトキシシラン等のエチルシラン化合物;
ブチルジメトキシシラン、ブチルメトキシエトキシシラン、ブチルジエトキシシラン、ブチルメトキシプロポキシシラン、ブチルメトキシペンチルオキシシラン、ブチルエトキシプロポキシシラン、ブチルジプロポキシシラン、ブチルジペンチルオキシシラン、ブチルジフェニルオキシシラン、ブチルメトキシフェニルオキシシラン等のブチルヒドロシラン化合物;
ジ(ヒドロキシフェニル)ジメトキシシラン、ジ(ヒドロキシフェニル)メトキシエトキシシラン、ジ(ヒドロキシフェニル)メトキシプロポキシシラン、ジ(ヒドロキシフェニル)ジエトキシシラン、ジ(ヒドロキシフェニル)ジペンチルオキシシラン、ジ(ヒドロキシフェニル)ジフェニルオキシシラン、ジ(ヒドロキシフェニル)エトキシプロポキシシラン、ジ(ヒドロキシフェニル)ジプロポキシシラン等のジ(ヒドロキシフェニル)シラン化合物;
シラン化合物(b)は、1種を単独で使用してもよく2種以上を併用してもよい。
例えば、テトラメトキシシランのモノマーに所定量の水及び必要に応じて有機溶剤を加え、触媒の存在下に、副生するアルコールを留去しながら通常、室温程度~100℃で反応させる。これにより、テトラメトキシシランの加水分解及び縮合が進行して、液状のテトラメトキシシラン部分加水分解縮合物(平均重合度は通常2~8程度、大部分は3~7)が生成する。液状のテトラメトキシシラン部分加水分解縮合物は、例えば、CH3O-(Si(OCH3)2-O)s-CH3で表される。sは平均重合度を表す2~8の数である。加水分解の程度は、使用する水の量により適宜調節することができる。
上記のようにして得られた液状のテトラメトキシシラン部分加水分解縮合物をさらに加水分解縮合反応させてもよい。液状のテトラメトキシシラン部分加水分解縮合物をさらに加水分解縮合反応させる方法は、後述する一次反応物を二次反応物とする方法と同様である。
テトラメトキシシラン以外のシラン化合物(b)の場合も同様にして部分加水分解縮合物とすることができる。2種以上のシラン化合物(b)の混合物を部分加水分解縮合物としてもよい。
酸触媒の使用量は、触媒としての機能を発揮し得る量であれば特に制限されるものではないが、通常、シラン化合物(b)100質量部に対し、0.001~10質量部程度の範囲から選択され、好ましくは0.003~5質量部である。
成分(B)のMwは、ゲルパーミエーションクロマトグラフィ(GPC)により測定される標準ポリスチレン換算の値である。
成分(B)として二次反応物を用いることで、本樹脂組成物の硬化性、硬化物の外観を高めることができる。その理由は明らかではないが、以下のことが考えられる。二次反応物においては、加水分解が促進されているため、一次反応物に比べ、シラノール基(Si-OH)が多量に存在する。シラノール基はSi-OR5に比べて反応性が高いので、硬化性が向上する。また、縮合反応が促進されるので分子量が大きくなりクラックを抑制するため外観を向上することができる。
一次反応物を形成するシラン化合物(b)としては、硬化物の硬度の観点から、シラン化合物(b1)が好ましく、テトラアルコキシシランであることがより好ましく、テトラメトキシシランであることがさらに好ましい。
一次反応物は、前記したように、シラン化合物(b)又はその2種以上の混合物を加水分解縮合反応させることにより得られる。
なお、一次反応物は市販のものを使用することもでき、例えば三菱ケミカル製のMS51、MS53、MS57、MS56S、コルコート製のエチルシリケート40、エチルシリケート48、メチルシリケート51、メチルシリケート53A、EMS-485等が挙げられる。
一次反応物を触媒の存在下にさらに加水分解縮合反応させて二次反応物とさせる方法としては、一次反応物に水、触媒及び溶剤を添加し25℃で1日以上撹拌する方法が挙げられる。さらに一次反応物を加熱することで反応の進行を促進することができ、その場合は例えば30℃~100℃で1時間以上撹拌する方法もとることができる。
本樹脂組成物が開始剤(C)を含むことで、成分(B)及び基(1)の加水分解縮合反応が進みやすくなり、本樹脂組成物の硬化性が向上する。
開始剤(C)としては、光重合開始剤、熱重合開始剤、金属触媒、酸触媒等が挙げられる。
熱重合開始剤としては、例えば熱ラジカル重合開始剤、熱酸発生剤、熱塩基発生剤が挙げられる。
金属触媒又は酸触媒としては、シラン化合物(b)の部分加水分解縮合物を得る際に用いられる触媒と同様のものが挙げられる。これらはいずれか1種を単独で用いてもよく2種以上を併用してもよい。
本樹脂組成物が希釈剤を含むと、本樹脂組成物を基材に塗工する際の塗工作業性、形成される塗膜及びその硬化膜の平滑性及び均一性、並びに硬化膜の基材に対する密着性が向上する。
希釈剤としては、水、有機溶剤等が挙げられ、有機溶剤が好ましい。
成分(B)がシラン化合物(b)の加水分解縮合物である場合、希釈剤は、シラン化合物(b)を加水分解縮合反応させるために配合された水を含んでいてもよい。
グリコール系溶剤としては、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノn-プロピルエーテル、エチレングリコールモノn-ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート等が挙げられる。
エステル系溶剤としては、酢酸メチル、酢酸エチル、酢酸ブチル、アセト酢酸メチル、アセト酢酸エチル等が挙げられる。
ケトン系溶剤としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、アセチルアセトン等が挙げられる。
エーテル系溶剤としては、エチルエーテル、ブチルエーテル、メチルセロソルブ、エチルセロソルブ、ジオキサン、フラン、テトラヒドロフラン等が挙げられる。
有機溶剤は1種単独で用いてもよく2種以上を併用してもよい。
他の成分としては、例えば、共重合体(A)以外の重合体、紫外線吸収剤、光安定剤、シランカップリング剤、無機微粒子、酸化防止剤、黄変防止剤、ブルーイング剤、顔料、レベリング剤、消泡剤、増粘剤、沈降防止剤、帯電防止剤及び防曇剤等が挙げられる。
共重合体(A)の含有量は、樹脂組成物中の不揮発成分の合計100質量%に対し、1~95質量%が好ましく、10~90質量%がより好ましく、20~85質量%がさらに好ましく、25~85質量%が特に好ましく、30~70質量%が最も好ましい。共重合体(A)の含有量が上記下限値以上であれば、硬化物の滑水性、外観がより優れ、上記上限値以下であれば、硬化物の外観、強度がより優れる。
なお、不揮発成分とは、有機溶剤を除く分を表す。
上記のようにして硬化膜を形成し、50℃、99%RH以上の条件にて96時間の耐久性試験を実施した後の前記硬化膜(耐久性試験後の硬化膜)の表面の23℃、20μLの水の滑落角は、60°以下が好ましく、50°以下がより好ましく、40°以下がさらに好ましく、30°以下が特に好ましく、20°以下が最も好ましい。水の滑落角の下限に関しては特に制限はなく、例えば1°以上である。
上記のようにして硬化膜を形成し、60分中12分の降雨、照射強度180W/m2(300~400nm)、ブラックパネル温度63℃、槽内温度50℃、槽内湿度50%の条件にて500時間の耐候性試験を実施した後の前記硬化膜(耐久性試験後の硬化膜)の表面の23℃、20μLの水の滑落角は、60°以下が好ましく、50°以下がより好ましく、40°以下がさらに好ましく、30°以下が特に好ましく、20°以下が最も好ましい。水の滑落角の下限に関しては特に制限はなく、例えば1°以上である。
本樹脂組成物は、共重合体(A)、成分(B)、必要に応じて開始剤(C)、希釈剤、他の成分を混合することにより製造できる。
希釈剤が水を含む場合、水は、シラン化合物(b)の加水分解縮合物の調製時に配合されてもよく、本樹脂組成物の製造時に配合されてもよく、シラン化合物(b)の加水分解縮合物の調製時及び本樹脂組成物の製造時の両方で配合されてもよい。
本樹脂組成物の用途としては、上記の中でも、センシング部材用途が好適である。例えば、車両においてミリ波レーダーやLiDARの前面側に位置するエンブレムやフロントグリルの表面材を本樹脂組成物の硬化物で構成した場合、エンブレム等の最表面に雨滴や雪が付着しても容易に滑落し、ミリ波レーダーやLiDARの電磁波が雨滴や雪により減衰や散乱を受けることを抑制できる。
本発明の一態様に係る硬化物(以下、「本硬化物」とも記す。)は、本樹脂組成物の硬化物である。
硬化方法としては、本樹脂組成物に活性エネルギー線を照射する方法、加熱により硬化する方法、空気中の湿気を利用して硬化する方法等が挙げられ、基材にかかる温度と生産性の観点から、本樹脂組成物に活性エネルギー線を照射する方法が好ましい。
紫外線照射によって本樹脂組成物を硬化する場合、光源としては、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、UV-LED、低圧水銀灯、キセノンエキシマランプ等を用いることができる。生産性の観点から、波長150~420nmに最大照射強度を示す光源を用いることが好ましい。また、紫外線の積算照射量は、50~3000mJ/cm2が好ましく、100~2000mJ/cm2がより好ましい。
上記のようにして硬化物を形成し、50℃、99%RH以上の条件にて96時間の耐久性試験を実施した後の前記硬化物(耐久性試験後の硬化物)の表面の23℃、20μLの水の滑落角は、60°以下が好ましく、50°以下がより好ましく、40°以下がさらに好ましく、30°以下が特に好ましく、20°以下が最も好ましい。水の滑落角の下限に関しては特に制限はなく、例えば1°以上である。
上記硬化物は、例えば、共重合体(A)と、少なくとも1種のシラン化合物(b)又はその部分加水分解縮合物からなる成分(B)とを含む硬化性組成物を基材上に塗工し、硬化させる(硬化物形成工程)ことで製造できる。
硬化物形成工程の後、必要に応じて、形成された硬化物と基材とを剥離してもよい。
硬化性組成物は、共重合体(A)と成分(B)とを含む。
硬化性組成物は、典型的には、希釈剤を含む。
硬化性組成物は、開始剤(C)を含むことが好ましい。
硬化性組成物は、必要に応じて、上記以外の他の成分を含んでいてもよい。
共重合体(A)、開始剤(C)、他の成分はそれぞれ前記したとおりである。
成分(B)は、少なくとも1種のシラン化合物(b)又はその部分加水分解縮合物からなる。シラン化合物(b)は前記したとおりである。
例えば、テトラメトキシシランのモノマーに所定量の水及び必要に応じて有機溶剤を加え、触媒の存在下に、副生するアルコールを留去しながら通常、室温程度~100℃で反応させる。これにより、テトラメトキシシランの加水分解及び縮合が進行して、液状のテトラメトキシシラン部分加水分解縮合物(平均重合度は通常2~8程度、大部分は3~7)が生成する。液状のテトラメトキシシラン部分加水分解縮合物は、例えば、CH3O-(Si(OCH3)2-O)s-CH3で表される。sは平均重合度を表す2~8の数である。加水分解の程度は、使用する水の量により適宜調節することができる。
上記のようにして得られた液状のテトラメトキシシラン部分加水分解縮合物をさらに加水分解縮合反応させてもよい。液状のテトラメトキシシラン部分加水分解縮合物をさらに加水分解縮合反応させる方法は、後述する一次反応物を二次反応物とする方法と同様である。
テトラメトキシシラン以外のシラン化合物(b)の場合も同様にして部分加水分解縮合物とすることができる。2種以上のシラン化合物(b)の混合物を部分加水分解縮合物としてもよい。
ビス(イソプロポキシ)ビス(アセチルアセトネート)等の金属キレート化合物、ホウ酸ブトキシド、ホウ酸等のホウ素化合物等が挙げられる。
酸触媒の使用量は、触媒としての機能を発揮し得る量であれば特に制限されるものではないが、通常、シラン化合物(b)100質量部に対し、0.001~10質量部程度の範囲から選択され、好ましくは0.003~5質量部である。
成分(B)のMwは、ゲルパーミエーションクロマトグラフィ(GPC)により測定される標準ポリスチレン換算の値である。
成分(B)として二次反応物を用いることで、硬化性組成物の保存安定性を充分に維持しつつ、硬化性組成物の硬化性、外観を優れたものとすることができる。その理由は明らかではないが、以下のことが考えられる。二次反応物においては、加水分解が促進されているため、一次反応物に比べ、シラノール基(Si-OH)が多量かつ安定に存在することができる。シラノール基はSi-OR5に比べて反応性が高いので、硬化性が向上する。また、縮合反応が促進されるので分子量が大きくなりクラックを抑制するため外観を向上することができる。
一次反応物を形成するシラン化合物(b)としては、硬化層の硬度の観点から、シラン化合物(b1)が好ましく、テトラアルコキシシランがより好ましく、テトラメトキシシランがさらに好ましい。
一次反応物は、前記したように、シラン化合物(b)又はその2種以上の混合物を加水分解縮合反応させることにより得られる。
なお、一次反応物は市販のものを使用することもでき、例えば三菱ケミカル製のMS51、MS53、MS57、MS56S、コルコート製のエチルシリケート40、エチルシリケート48、メチルシリケート51、メチルシリケート53A、EMS-485等が挙げられる。
一次反応物を触媒の存在下に加水分解縮合反応させる方法としては、一次反応物に水、触媒及び溶剤を添加し25℃で1日以上撹拌する方法が挙げられる。さらに一次反応物を加熱することで反応の進行を促進することができ、その場合は例えば30℃~100℃で1時間以上撹拌する方法も取ることができる。
二次反応物のMwは、本発明者らの検討のなかでの経験的な温度や反応時間から、400~50000が好ましく、600~30000がより好ましく、800~10000がさらに好ましく、900~5000が特に好ましく、1000~2000が最も好ましい。
硬化性組成物が希釈剤を含むと、硬化性組成物を塗工する際の塗工作業性、形成される硬化物の平滑性及び均一性、基材と硬化物との間の密着性が向上する。
希釈剤としては、水、有機溶剤等が挙げられ、有機溶剤が好ましい。
有機溶剤としては、アルコール系溶剤、グリコール系溶剤、炭化水素系溶剤、エステル系溶剤、ケトン系溶剤、エーテル系溶剤等が挙げられる。
グリコール系溶剤としては、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノn-プロピルエーテル、エチレングリコールモノn-ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート等が挙げられる。
エステル系溶剤としては、酢酸メチル、酢酸エチル、酢酸ブチル、アセト酢酸メチル、アセト酢酸エチル等が挙げられる。
ケトン系溶剤としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、アセチルアセトン等が挙げられる。
エーテル系溶剤としては、エチルエーテル、ブチルエーテル、メチルセロソルブ、エチルセロソルブ、ジオキサン、フラン、テトラヒドロフラン等が挙げられる。
有機溶剤は1種単独で用いてもよく2種以上を併用してもよい。
成分(B)がシラン化合物(b)の加水分解縮合物である場合、希釈剤は、シラン化合物(b)を加水分解縮合反応させるために配合された水を含んでいてもよい。
なお、不揮発成分とは、希釈剤を除く成分を表す。
希釈剤が水を含む場合、水は、シラン化合物(b)の加水分解縮合物の調製時に配合されてもよく、硬化性組成物の製造時に配合されてもよく、シラン化合物(b)の加水分解縮合物の調製時及び本組成物の製造時の両方で配合されてもよい。
硬化性組成物の塗工方法としては、ハケ塗り、グラビアコーター法、ダイコーター法、バーコーター法、スプレーコート法、フローコート法、ディップコート法、スピンコート法及びカーテンコート法等の公知の方法を用いることができる。
紫外線照射によって硬化性組成物を硬化する場合、光源としては、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、UV-LED、低圧水銀灯、キセノンエキシマランプ等を用いることができる。生産性の観点から、波長150~420nmに最大照射強度を示す光源を用いることが好ましい。また、紫外線の積算照射量は、50~3000mJ/cm2が好ましく、100~2000mJ/cm2がより好ましい。
活性エネルギー線は、空気雰囲気中で照射してもよいし、窒素、アルゴン等の不活性ガス雰囲気中で照射してもよい。
本発明の一態様に係る積層体(以下、「本積層体」とも記す。)は、基材と、硬化物からなる層(以下、「硬化物層」とも記す。)と、を有する。
硬化物層は、本積層体の最表層に位置することが好ましい。
基材と硬化物層との間にプライマー層を有していてもよい。
紫外線吸収剤や光安定剤は、積層体のどの層に含まれてもかまわない。しかしながら、部材保護の観点、積層体の硬化層の硬化のしやすさや滑水性の性能保持の観点から、紫外線吸収剤や光安定剤は、基材又はプライマー層に含まれることが好ましく、積層体全体の設計のしやすさを考慮すると、プライマー層に含まれることがより好ましい。
積層体においては、特に基材又はプライマー層に光安定剤が含まれることが好ましく、積層体全体の設計のしやすさを考慮すると、プライマー層に光安定剤が含まれることがより好ましい。光安定剤は、光で生成するラジカルを捕捉できるので、光(特に紫外線)に対する耐性を向上させることができる。特に、光安定剤とともに紫外線吸収剤が含まれることが好ましい。
基材としては、ガラス基材;亜鉛メッキ鋼板、亜鉛合金メッキ鋼板、ステンレス鋼板、錫メッキ鋼板等の金属基材;ポリメタクリル酸メチル樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリスチレン樹脂、ABS樹脂、AS樹脂、ポリアミド樹脂、ポリアリレート樹脂、ポリウレタン樹脂、ポリビニル樹脂、トリアセチルセルロース、ポリメタクリルイミド樹脂及びポリアリルジグリコールカーボネート樹脂等の樹脂基材が挙げられる。樹脂基材を構成する樹脂としては、積層体を各種の部材に使用することを考えると、透明性や機械強度の観点から、ガラス、ポリカーボネート樹脂、ポリエステル樹脂、トリアセチルセルロース、ポリウレタン樹脂又はポリビニル樹脂が好ましく、ポリカーボネート樹脂又はポリエステル樹脂が好ましい。樹脂基材は、樹脂の他に、紫外線吸収剤、光安定剤、可塑剤、帯電防止剤、難燃剤、補強材、充填剤、着色剤、滑剤、発泡剤、易滑剤、硬化触媒等の添加剤を含んでいてもよい。
必要に応じて、基材上に密着性の向上等のためにプライマー層が存在していてもよいし、基材の硬化物層が存在する側とは反対側に粘着層、防曇層、反射防止層等の機能層を有することも可能である。また、積層体の最表面とは反対側または内部にヒーターを搭載してもよい。
プライマー層は、基材と硬化層との間の密着性、硬化層を積層する際の塗工性の向上に寄与する。検討を続ける中で、従来、樹脂基材を用いる場合に、硬化層の成分との違いが大きいため、密着性(基材と硬化層との付着性)が悪くなりやすいことが判明した。そのため、基材として樹脂基材を使用する場合には基材との密着性、及び硬化層との密着性の双方を達成するために基材と硬化層との中間にプライマー層を設けることにより当該密着性の課題を解決できることを見出した。
プライマー層は、典型的には、樹脂成分を含む。
プライマー層は、紫外線吸収剤及び光安定剤からなる群から選ばれる少なくとも1種を含むことが好ましい。
プライマー層は、必要に応じて、本発明の効果を損なわない範囲で、紫外線吸収剤及び光安定剤以外の他の添加剤を含んでいてもよい。
樹脂成分としては、例えばアクリル樹脂、ポリエステル樹脂、ウレタン樹脂、ビニル樹脂等が挙げられる。これらの中でも特に密着性を向上させるという観点から、アクリル樹脂又はウレタン樹脂が好ましい。これらの樹脂成分は1種単独で用いてもよく2種以上を併用してもよい。また、樹脂成分としては、非硬化性の樹脂でもよいし、硬化性化合物(モノマー、オリゴマー等)由来の化合物でもよい。硬化性化合物由来の化合物としては、硬化性化合物の硬化物が挙げられる。
硬化性化合物由来の化合物は、硬化層との密着性のさらなる向上、硬化層の耐久性の向上の観点から好ましい。プライマー層を形成するプライマーに硬化性化合物を含有させ、プライマーを基材上に塗布し、基材上で硬化性化合物を硬化させることで、硬化性化合物由来の化合物を含むプライマー層が形成される。かかるプライマー層は、樹脂成分が非硬化性の樹脂のみである場合に比べて、基材への付着性に優れ、基材と硬化層との間の密着性が向上する。また、プライマー層に硬化性化合物を用いることで、非硬化性化合物を用いる場合に比べて、硬化層の耐久性(耐久性試験後の外観、基材との間の密着性、滑水性等)に優れる傾向がある。
硬化性化合物としては、活性エネルギー線硬化性化合物や熱硬化性化合物が挙げられ、活性エネルギー線硬化性化合物が好ましい。プライマーを樹脂基材に塗工した後、熱により硬化させると、樹脂基材が熱により変形するおそれがあるが、活性エネルギー線により硬化させれば、樹脂基材の熱による変形を抑えられるので、耐熱性の低い樹脂基材にも適用できる。また、一般的に活性エネルギー線による硬化は熱硬化や湿気硬化等の他の硬化方法と比べて硬化時間が短く生産性の向上が期待できる。
ラジカル重合性基を有する化合物としては、従来公知の各種の化合物を使用することができ、例えば(メタ)アクリレート、(メタ)アクリレートと共重合可能な他のモノマー等が挙げられる。また、ラジカル重合性基を有する化合物としては、ラジカル重合性基を1つ有する単官能化合物、ラジカル重合性基を2つ有する2官能化合物、ラジカル重合性基を3つ以上有する3官能以上の多官能化合物が挙げられる。これらの中でも、硬化層との密着性を向上させるために硬化度を高めたプライマー層とするために、多官能化合物を含むことが好ましい。
多官能(メタ)アクリレートとしては、特に限定されるものではないが、例えばペンタエリスリトールトリアクリレート、ジペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、トリメチロールプロパントリアクリレート、ネオペンチルグリコール変性トリメチロールプロパンジ(メタ)アクリレート等のトリメチロールプロパン由来の骨格を有する(メタ)アクリレート、ジトリメチロールプロパンテトラアクリレート、ビス(2-アクリロイルオキシエチル)-2-ヒドロキシエチルイソシアヌレート等のイソシアヌレート骨格を有する(メタ)アクリレート;無水コハク酸へのペンタエリスリトールトリアクリレート付加物、無水コハク酸へのジペンタエリスリトールペンタアクリレート付加物等の多官能アクリレート;側鎖又は側鎖と末端にアクリロイル基を有するポリエステルオリゴマー(具体的には、東亞合成製のM8030、M7100等)等のポリエステル(メタ)アクリレート;イソホロンジイソシアネート(IPDI)のイソシアヌレート体、ポリテトラメチレングリコール(PTMG)及びヒドロキシエチルアクリレート(HEA)の反応物、ヘキサメチレンジイソシアネート(HDI)とPTMG反応物へのペンタエリスリトールトリアクリレートの反応物等の多官能ウレタン(メタ)アクリレート;ポリカーボネートジオールを用いたオリゴエステルとペンタエリスリトールトリアクリレートの反応物等のカーボネート結合を有するポリエステル(メタ)アクリレート;ジイソシアネートと3官能以上のポリオールの反応物と、水酸基含有(メ
タ)アクリレートの反応物等のポリウレタン(メタ)アクリレート;トリエトキシイソシアヌル酸トリアクリレート等のイソシアヌレート環を有するトリエトキシ(メタ)アクリレート;これらのアルキレンオキサイド変性物;これらのポリカプロラクトン変性物等が挙げられる。
これらの中でも、粘度及び硬化性、並びに硬化膜の硬度の観点から、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、トリメチロールプロパントリアクリレート、ジトリメチロールプロパンテトラアクリレート、ジペンタエリスリトールトリアクリレート;これらのアルキレンオキサイド変性体;これらのカプロラクトン変性体を含むことが好ましい。
(メタ)アクリレートは1種のみで用いてもよいし、2種以上を組み合わせて用いてもよい。
これらのポリオールは単独で用いても、複数種併用してもよい。
紫外線吸収剤としては、例えば有機系紫外線吸収剤と無機系紫外線吸収剤が挙げられる。透明性の観点からは有機系紫外線吸収剤が好ましい。
有機系紫外線吸収剤としては、特に限定されないが、例えば、ヒドロキシフェニルトリアジン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、環状イミノエステル系紫外線吸収剤、ベンゾフェノン系紫外線吸収剤、サリチル酸エステル系紫外線吸収剤、シアノアクリレート系紫外線吸収剤等が挙げられる。これらの中でも、耐候性、耐久性の観点からはヒドロキシフェニルトリアジン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、環状イミノエステル系紫外線吸収剤がより好ましく、ヒドロキシフェニルトリアジン系紫外線吸収剤がさらに好ましい。これらの紫外線吸収剤は1種単独で用いてもよく2種類以上併用して用いてもよい。さらに、これらの化合物をポリマーに組み入れたものを使用することも可能である。
光安定剤としては、特に限定されないが、例えば、アミン系光安定剤、フェノール系光安定剤、リン系光安定剤、チオエーテル系光安定剤等が挙げられ、これらの中でもアミン系光安定剤、フェノール系光安定剤、リン系光安定剤が好ましく、特に黄変性が少ないこと等を考慮するとアミン系光安定剤がより好ましい。これら光安定剤は、1種単独で用いてもよく2種類以上併用して用いることも可能である。また、これらの化合物をポリマーに組み入れたものを使用することも可能である。
ル)-pクレゾール]、1,3,5-トリス(4-第3級ブチル-3-ヒドロキシ-2,6-ジメチルベンジル)イソシアヌル酸、1,3,5-トリス(3,5-ジ-第3級ブチル-4-ヒドロキシベンジル)イソシアヌル酸、トリエチレングリコール-ビス[3-(3-第3級ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオネート]、2,2’-オキサミドビス[エチル3-(3,5-ジ-第3級ブチル-4-ヒドロキシフェニル)プロピオネート]、6-(4-ヒドロキシ-3,5-ジ-第3級ブチルアニリノ)-2,4-ジオクチルチオ-1,3,5-トリアジン、ビス[2-第3級ブチル-4-メチル-6-(2-ヒドロキシ-3-第3級ブチル-5-メチルベンジル)フェニル]テレフタレート、3,9-ビス{2-[3-(3-第3級ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニルオキシ]-1,1-ジメチルエチル}-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン、3,9-ビス{2-[3-(3,5-ジ-第3級ブチル-4-ヒドロキシフェニル)プロピオニルオキシ]-1,1-ジメチルエチル}-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン等が挙げられる。
他の添加剤としては、例えば、レベリング剤、シランカップリング剤、消泡剤、増粘剤、帯電防止剤、赤外線吸収剤、発泡剤、無機微粒子、有機微粒子、染料、顔料、酸化防止剤、黄変防止剤、ブルーイング剤、防曇剤、沈降防止剤、密着性付与剤等が挙げられる。
マルテンス硬度の測定方法は、後述する実施例に記載のとおりである。
プライマー層のマルテンス硬度は、プライマー層を構成する樹脂成分の種類、架橋密度等により調整できる。
水の接触角の測定方法は、後述する実施例に記載のとおりである。
水の接触角は、レベリング剤の添加量、親水性基(水酸基、アミノ基、スルホニル基、カルボキシル基、及びそれらの塩等)をもつ原料の含有量等により調整できる。具体的には、レベリング剤の添加量を減らす、表面張力低下能の低いレベリング剤に変更する、又は親水性基を持つ原料の含有量を増やすと、水の接触角が小さくなる傾向がある。
本積層体は、例えば、基材の上にプライマー層を形成し(プライマー層形成工程)、プライマー層の上に、共重合体(A)と、少なくとも1種のシラン化合物(b)又はその部分加水分解縮合物からなる成分(B)とを含む硬化性組成物を塗工し、硬化させて硬化層を形成する(硬化層形成工程)ことにより製造できる。
プライマー層を形成する方法としては、例えば、樹脂成分及び希釈剤を含むプライマーを、基材のうえに塗工し、乾燥によって希釈剤を除去する方法が挙げられる。
プライマーは、紫外線吸収剤及び光安定剤からなる群から選ばれる少なくとも1種を含むことが好ましい。
プライマーは、必要に応じて、本発明の効果を損なわない範囲で、紫外線吸収剤及び光安定剤以外の他の添加剤を含んでいてもよい。
樹脂成分、紫外線吸収剤、光安定剤、他の添加剤はそれぞれ前記したとおりである。
有機溶剤としては、アルコール系溶剤、グリコール系溶剤、炭化水素系溶剤、エステル系溶剤、ケトン系溶剤、エーテル系溶剤等が挙げられる。アルコール系溶剤としては、メタノール、エタノール、イソプロピルアルコール、nブタノール、イソブタノール、オクタノール、n-プロピルアルコール、アセチルアセトンアルコール等が挙げられる。グリコール系溶剤としては、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノn-プロピルエーテル、エチレングリコールモノn-ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート等が挙げられる。炭化水素系溶剤としては、ベンゼン、ケロシン、トルエン、キシレン等が挙げられる。エステル系溶剤としては、酢酸メチル、酢酸エチル、酢酸ブチル、アセト酢酸メチル、アセト酢酸エチル等が挙げられる。ケトン系溶剤としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、アセチルアセトン等が挙げられる。エーテル系溶剤としては、エチルエーテル、ブチルエーテル、メチルセロソルブ、エチルセロソルブ、ジオキサン、フラン、テトラヒドロフラン等が挙げられる。有機溶剤は1種単独で用いてもよく2種以上を併用してもよい。
硬化方法としては、前記と同様の方法が挙げられ、硬化性組成物に活性エネルギー線を照射する方法が好ましい。
上記のようにして硬化物層を形成し、50℃、99%RH以上の条件にて96時間の耐久性試験を実施した後の前記硬化物層(耐久性試験後の硬化物層)の表面の23℃、20μLの水の滑落角は、60°以下が好ましく、50°以下がより好ましく、40°以下がさらに好ましく、30°以下が特に好ましく、20°以下が最も好ましい。水の滑落角の下限に関しては特に制限はなく、例えば1°以上である。
耐久性試験後の硬化物層の水の滑落角の初期の硬化物層の水の滑落角からの変化量(耐久性試験後の硬化物層の水の滑落角-初期の硬化物層の水の滑落角)としては、40°以下が好ましく、30°以下がより好ましく、20°以下がさらに好ましく、15°以下が最も好ましい。下限は特にないが、好ましくは0°である。当該範囲とすることで、長期間において初期と同程度の性能を発現させることができ、商品設計がしやすいものとなる。
<Mwの測定>
本実施例において製造した共重合体及びシラン化合物の部分加水分解縮合物のMwは、ゲルパーミエーションクロマトグラフィー(GPC)により以下の条件で測定した。
機器:Waters製「e2695」、
カラム:東ソー製「TSKgel Super H3000+H4000+H6000」、
検出器:示差屈折率検出器(RI検出器/内蔵)、
溶媒:テトラヒドロフラン、
温度:40℃、
流速:0.5mL/分、
注入量:10μL、
濃度:0.2質量%、
校正試料:単分散ポリスチレン、
校正法:ポリスチレン換算。
評価サンプルの外観は、目視により評価した。判定基準は次のとおりである。
(判定基準)
A:白化・クラック・ふくれ等の異常が見られず透明で平滑な塗膜が形成されている。
B:白化・クラック・ふくれ等の異常がわずか見られる。
C:白化・クラック・ふくれ等の異常がみられる。
評価サンプルの硬化膜面について、23℃、55%RHの雰囲気下、評価者の利き手の親指の爪で強く3往復させた。硬化膜の傷付き度合いを、目視にて以下の基準で評価した。
A:外観変化なし。
B:傷がつく。
C:塗膜がはがれる。
評価サンプルの硬化膜面について、滑落法で断続傾斜により基材を傾けることで23℃、20μLの水の滑落角を測定し、滑水性を評価した。具体的には、23℃、50%RHの環境下で、サンプル固定台の上に水平に配置した評価サンプルの硬化膜面に、接触角計(DM-500、協和界面科学製)を用いて、20μLの蒸留水の液滴を滴下した後、評価サンプルを1°ずつ断続的に傾けていき、液滴が滑り出したときの傾斜角を滑落角とした。滑水性の判定基準は次の通りである。
(判定基準)
A:滑落角が1°より大きく40°以下。
B:滑落角が41°より大きく60°以下。
C:傾斜角が60°を超える、又は90°でも水滴が滑落しない。
フィッシャー・インストルメンツ製、FISCHERSCOPE(登録商標)HM2000を用いて、以下の試験条件で、23℃におけるプライマー層のマルテンス硬度を測定した。
(試験条件)
圧子:ビッカース圧子
荷重の増加パラメーター:dSQRT(F)/dt=一定
最大荷重:1mN
荷重アプリケーション時間=20秒
クリープ=0秒
荷重の減少パラメーター:dSQRT(F)/dt=一定
(試験片の作製方法)
基材:ポリカーボネート板(PC,3mm厚)、
塗工:スプレー塗工、
乾燥膜厚:13μm、
硬化条件:プライマーが活性エネルギー線硬化性の場合は、高圧水銀灯2000mJ/cm2、プライマーが熱硬化性の場合は、120℃×30分。
なお、基材の種類や膜厚によってマルテンス硬度の値は変化する。
液滴法により水の接触角を測定した。具体的には、23℃、50%RHの環境下で、水平に配置した評価サンプルの硬化層表面(又は硬化層を形成する前のプライマー層表面)に、接触角計(DM-500、協和界面科学製)を用いて、1μLの蒸留水を滴下し、滴下から5秒後に接触角(静的接触角)を測定した。
セロハンテープ剥離により硬化層の付着性(プライマー層と硬化層との間の密着性)を評価した。具体的には23℃50%RHの環境下で評価サンプルの硬化層表面にセロハンテープを指で圧着し、素早く手前斜め45°の方向に引きはがし、目視にて、剥がれた硬化層の面積(剥離面積)を確認し、付着性を評価した。付着性の評価基準は以下のとおりである。
A:剥がれなし。
B:剥がれが見られるがセロハンテープの圧着面積に対して剥離面積が50%未満。
C:セロハンテープの圧着面積に対して剥離面積が50%以上。
評価サンプルの硬化膜に対し、湿潤試験機(装置名:湿潤試験機、型式 CT-3H、スガ試験機(株)製)を用いて、槽内温度50℃、槽内湿度99%RH以上の条件にて96時間の耐久性試験を実施した。
耐久性試験後に、上記の外観及び滑水性の評価を行った。
耐候性試験は、耐候性試験機(装置名:スーパーキセノンウェザーメーター、型式 SX75型、スガ試験機(株)製)を用いて、60分中12分の降雨、照射強度180W/m2(300~400nm)、ブラックパネル温度63℃、槽内温度50℃、槽内湿度50%の条件にて500時間の耐候性試験を実施した。なお、評価サンプルは、積層した硬化膜面と耐候性試験機の光源側が垂直となるように配置した。
以下において使用される略号の意味は以下のとおりである。
KBM-5103:信越化学工業製「KBM-5103」(3-アクリロキシプロピルトリメトキシシラン、不揮発成分100%)。
FM-0721:JNC株式会社製「サイラプレーンFM-0721」(片末端にメタクリロイル基を有するポリジメチルシロキサン、Mw4200、不揮発成分100%)。
FM-0711:JNC株式会社製「サイラプレーンFM-0711」(片末端にメタクリロイル基を有するポリジメチルシロキサン、Mw900、不揮発成分100%)。
FM-0721及びFM-0711の構造は以下のとおりである。
CH2=C(CH3)-COO-C3H6-(Si(CH3)2O)n-(CH2)3CH3
共重合体(A-2):後述する合成例2で得た共重合体(FM-0721:KBM5103=50:50(質量比)、Mw19800)。
共重合体(A-3):後述する合成例3で得た共重合体(FM-0711:KBM5103=30:70(質量比)、Mw15500)。
共重合体(A-4):後述する合成例4で得た共重合体(FM-0711:KBM5103=30:40(質量比)、Mw43000)。
共重合体(E-1):後述する合成例5で得た共重合体(FM-0721:KBM-5
103=0:100(質量比)、Mw23400)。
共重合体(E-2):後述する合成例6で得た共重合体(FM-0721:KBM-5
103=20:30(質量比)、Mw53300)。
成分(B-2):後述する合成例8で得たアルコキシシラン加水分解縮合物(Mw1600)。
MS51:三菱ケミカル社製「MS51」(テトラメトキシシラン部分加水分解縮合物、Mw800~1100、不揮発成分100%)。
IPA:2-プロパノール。
PGM:プロピレングルコールモノメチルエーテル。
パーオクタO:日油株式会社製「パーオクタO」(2-エチルヘキサンペルオキシ酸1,1,3,3-テトラメチルブチル)。
実施例及び比較例で使用した共重合体及びシラン化合物の部分加水分解縮合物の調製方法について説明する。なお、共重合体(A-1)~(A-4)は、共重合体(A)に該当するものであり、共重合体(E-1)、(E-2)は、共重合体(A)に該当しない比較品である。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の73.0g、FM-0721の41.7g、PGMの264.9g、パーオクタOの0.52gを投入した。また、滴下ロートへ、KBM-5103の73.0g、FM-0721の20.9g、PGMの225.3g、パーオクタOの0.52gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.21gを投入し、この1時間後にさらにパーオクタOの0.21gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発成分30%、重量平均分子量(Mw)16200の重合体であった。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の50.0g、FM-0721の60.0g、PGMの254.0g、パーオクタOの0.50gを投入した。また、滴下ロートへ、KBM-5103の50.0g、FM-0721の40.0g、PGMの216.0g、パーオクタOの0.50gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.20gを投入し、この1時間後にさらにパーオクタOの0.20gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発成分30%、重量平均分子量(Mw)19800の重合体であった。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の73.0g、FM-0711の41.7g、PGMの264.9g、パーオクタOの0.52gを投入した。また、滴下ロートへ、KBM-5103の73.0g、FM-0711の20.9g、PGMの225.3g、パーオクタOの0.52gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.21gを投入し、この1時間後にさらにパーオクタOの0.21gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発成分30%、重量平均分子量(Mw)15500の重合体であった。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の41.7g、FM-0721の41.7g、nーブチルメタクリラートの20.9g、2ーヒドロキシエチルメタクリラートの10.4g、PGMの267.7g、パーオクタOの0.52gを投入した。また、滴下ロートへ、KBM-5103の41.7g、FM-0721の20.9g、nーブチルメタクリラートの20.9g、2ーヒドロキシエチルメタクリラートの10.4g、PGMの222.2g、パーオクタOの0.52gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.21gを投入し、この1時間後にさらにパーオクタOの0.21gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発成分30%、重量平均分子量(Mw)43000の重合体であった。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の110.0g、PGMの254.0g、パーオクタOの0.50gを投入した。また、滴下ロートへ、KBM-5103の90.0g、PGMの216.0g、パーオクタOの0.50gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.20gを投入し、この1時間後にさらにパーオクタOの0.20gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発分30%、重量平均分子量(Mw)23400の重合体であった。
撹拌機、滴下ロート、冷却コンデンサー、温度計を備えた1000mLの5つ口セパラブルフラスコに、KBM-5103の31.3g、FM-0721の12.5g、nーブチルメタクリラートの41.7g、2ーヒドロキシエチルメタクリラートの10.4g、PGMの225.1g、パーオクタOの0.52gを投入した。また、滴下ロートへ、KBM-5103の31.3g、FM-0721の29.2g、nーブチルメタクリラートの41.7g、2ーヒドロキシエチルメタクリラートの10.4g、PGMの264.8g、パーオクタOの0.52gを投入した。次いで、オイルバス中にフラスコをセットし、窒素雰囲気下にて撹拌を開始し、内温が85℃になるまで昇温した。内温が85℃になってから30分後に滴下ロートより単量体混合物を2時間かけて滴下し1時間保持した後、パーオクタOの0.21gを投入し、この1時間後にさらにパーオクタOの0.21gを投入し、5時間反応を行った後に冷却した。得られた生成物は不揮発成分30%、重量平均分子量(Mw)53300の重合体であった。
MS51の308gに対し、メタノール624g、水65g及びアセチルアセトンアルミニウム(III)3gを配合し、室温で3日撹拌することで、無色透明で均一液状の成分(B-1)の溶液(成分(B-1)のSiO2換算の濃度:16wt%)を得た。
MS51の308gに対し、メタノール624g、水65g及びアセチルアセトンアルミニウム(III)3gを配合し、室温で7日撹拌することで、無色透明で均一液状の成分(B-2)の溶液(成分(B-2)のSiO2換算の濃度:16wt%)を得た。
<樹脂組成物の調製>
共重合体(A-1)の3.5部と、成分(B-1)の4.2部と、IPAの10部と、PGMの10部と、光酸発生剤CPI-200K(サンアプロ社製)の0.04部とを混合して樹脂組成物を調製した。
得られた樹脂組成物を、厚さ3mmのポリカーボネート樹脂板(PC板)(三菱エンジニアリングプラスチックス社製、商品名:「IUPILON ML-300」)の表面に、乾燥後の厚さが0.7μmとなるようにスプレー塗工した後、予め60℃に加熱した熱風乾燥機中で120秒間加熱して塗膜を乾燥(溶剤を揮発)させた。次いで、乾燥後の塗膜に対し、空気雰囲気中で、高圧水銀灯(アイグラフィック製、USX5-0902)を用いて1000mJ/cm2(波長340~380nmにおける積算照射量を、紫外線光量計UV-351(オーク製作所製)を用いて測定)の紫外線を照射して塗膜を硬化させ、PC板上に樹脂組成物の硬化膜が積層された評価サンプルを得た。
得られた樹脂組成物について硬化性を評価した。また、得られた評価サンプルについて、初期(耐久性試験前)の外観及び滑水性、耐久性試験後の外観及び滑水性を評価した。結果を表1に示した。
組成物に配合する成分の種類と配合量(部)を表1及び表2に示すようにした以外は実施例1と同様にして、組成物を調製し、評価サンプルを作製した。組成物及び評価サンプルの評価結果を表1及び表2に示した。ただし、比較例5は、組成物の液状態での相溶性が低位であり、硬化膜として成形できなかったため、評価サンプルの作製及び評価は行わなかった。
組成物に配合する成分の種類と配合量(部)を表1に示すようにした以外は実施例1と同様にして、組成物を調製した。この組成物を用い、基材をPC板から厚さ5mmのガラス板に変更した以外は実施例1と同様にして、評価サンプルを作製した。組成物及び評価サンプルの評価結果を表1に示した。
評価サンプルの作製において、組成物をスプレー塗工した後、紫外線を照射せず、予め150℃に加熱した熱風乾燥機中で10秒間加熱して硬化させた以外は参考例1と同様にして、組成物を調製し、評価サンプルを作製した。組成物及び評価サンプルの評価結果を表2に示した。
<硬化性組成物の調製>
共重合体(A-1)の溶液の3.5部と、成分(B-1)の溶液の4.2部と、IPAの10部と、PGMの10部と、光酸発生剤CPI-200Kを0.04部とを混合して硬化性組成物を調製した。
ジペンタエリスリトールヘキサアクリレート(DPHA)のカプロラクトン変性体(日本化薬社製「DPCA-20」)22部及びウレタンアクリレート16部を混合した樹脂中に、光重合開始剤としてベンゾフェノンを0.9部、紫外線吸収剤としてチヌビン400(BASF社製)を3部、光安定剤としてチヌビン123(BASF社製)を0.15部添加した後、プロピレングリコールモノメチルエーテルで不揮発成分が32質量%になるように希釈し、活性エネルギー線硬化性のプライマー(1)を調製した。
なお、ウレタンアクリレートは以下のようにして調製した。
保温機能付き滴下ロート、還流冷却器、撹拌羽根及び温度センサーを装備したフラスコ中に、ジシクロヘキシルメタンジイソシアネート530g(2mol)、ジラウリン酸ジn-ブチル錫300ppmを仕込み、40℃に加温した。その後、ポリオール化合物としてポリカーボネートジオール(商品名:クラレポリオールC-770、クラレ(株)製)800g(重量平均分子量800)650g(1mol)を4時間かけて滴下した。40℃にて2時間撹拌した後、1時間かけて70℃まで昇温させた。その後、2-ヒドロキシエチルアクリレート(HEA)232g(2mol)を2時間かけて滴下し、さらに2時間撹拌し、ウレタンアクリレートを得た。得られた生成物は不揮発成分75%、分子量1500の重合体であった。
厚さ3mmのポリカーボネート樹脂板(PC板)(三菱エンジニアリングプラスチックス社製、商品名:「IUPILON ML-300」)の上に、上記プライマー(1)をスプレー塗工後、予め70℃に加熱した熱風乾燥機中で90秒間加熱して塗膜を乾燥(溶剤を揮発)させた。次いで、乾燥後の塗膜に対し、空気雰囲気中で、高圧水銀灯を用いて2000mJ/cm2(波長340~380nmにおける積算照射量を、紫外線光量計UV-351(オーク製作所製)を用いて測定)の紫外線を照射して塗膜を硬化させ、厚さ13μmのプライマー層を形成した。
次いで、プライマー層の上に上記硬化性組成物を、乾燥後の厚さが700nmとなるようにスプレー塗工した後、予め60℃に加熱した熱風乾燥機中で120秒間加熱して塗膜を乾燥(溶剤を揮発)させた。次いで、乾燥後の塗膜に対し、空気雰囲気中で、高圧水銀灯(アイグラフィック製、USX5-0902)を用いて1000mJ/cm2(波長340~380nmにおける積算照射量を、紫外線光量計UV-351(オーク製作所製)を用いて測定)の紫外線を照射して塗膜を硬化させた。これにより、PC板上にプライマー層及び硬化層が順次積層された積層体を得た。
得られた評価サンプルについて、初期(耐久性試験前)の外観、付着性、接触角、滑落角、耐久性試験後の外観、付着性、接触角及び滑落角を評価した。結果を表3に示した。
組成物に配合する成分の種類と配合量(部)を表3及び表4に示すようにした以外は実施例11と同様にして、組成物を調製し、評価サンプルを作製した。組成物及び評価サンプルの評価結果を表3及び表4に示した。
ポリオールとしてBasonol(登録商標)HPE1170B(BASF社製)を100部、クラレポリオールC-1090(クラレ社製)を30部、イソシアネートとしてデュラネートMHG-80Bを159部(旭化成社製)、無機微粒子としてMEK-ST-40(日産化学社製)を70部、紫外線吸収剤としてチヌビン405(BASF社製)を30部、光安定剤としてチヌビン152(BASF社製)を0.5部、硬化促進触媒としてジブチル錫ジラウレート(DBTDL)を0.05部、を均一に混合し、さらにシクロヘキサノンとMIBKを用い、不揮発成分濃度が約32%となるように希釈して熱硬化性のプライマー(2)を調製した。
プライマー層を形成する際、硬化後の塗膜の厚さが10μmになるようにプライマー(2)をスプレー塗装し、120℃で30分間加熱処理することにより硬化膜(プライマー層)を形成した以外は実施例11と同様にして評価サンプルを作製した。評価結果を表3に示した。
非硬化性のアクリル樹脂としてBR-83(三菱ケミカル社製)の16部、紫外線吸収剤としてチヌビンPS(BASF社製)の2.2部、光安定剤としてチヌビン123(BASF社製)の1.8部をPGM及びメチルエチルケトン(MEK)を用いて不揮発成分濃度が16%となるように希釈し、均一に混合してプライマー(3)を調製した。
プライマー層を形成する際、乾燥後の塗膜の厚さが10μmになるようにプライマー(3)をスプレー塗装し、90℃で30分間加熱処理することにより非硬化性の塗膜(プライマー層)を形成した以外は実施例11と同様にして評価サンプルを作製した。評価結果を表3に示した。
PC板の代わりに厚さ100μmのポリカーボネートフィルム(PCフィルム,三菱エンジニアリングプラスチックス製FE-2000)を用い、プライマー層及び硬化層を形成する際、上記PCフィルムの上に上記プライマー(1)及び実施例12に記載の樹脂組成物を、バーコーターを用いて乾燥後の厚さがそれぞれ10μm及び700nmとなるよう塗工した以外は実施例11と同様にして評価サンプルを作製した。評価結果を表3に示した。
PC板の代わりに厚さ50μmのポリエチレンテレフタレートフィルム(PETフィルム,三菱ケミカル製ダイアホイルT600E50 W07)を用い、プライマー層及び硬化層を形成する際、上記PETフィルムの上に上記プライマー(1)及び実施例12に記載の樹脂組成物を、バーコーターを用いて乾燥後の厚さがそれぞれ10μm及び700nmとなるよう塗工した以外は実施例11と同様にして評価サンプルを作製した。評価結果を表3に示した。
<硬化性組成物の調製>
共重合体(A-1)の3.5部と、成分(B-1)の4.2部と、IPAの10部と、PGMの10部とを混合して硬化性組成物を調製した。
厚さ5mmのガラス板の上に、硬化後の厚さが0.7μmとなるように硬化性組成物をスプレー塗装し、150℃の熱風乾燥機中で1時間加熱して硬化させ、ガラス板上に硬化膜が積層された評価サンプルを得た。
得られた評価サンプルについて、初期(耐候性試験前)の外観及び滑水性、耐候性試験後の外観及び滑水性を評価した。結果を表5に示した。
硬化性組成物に配合する成分の種類と配合量(部)を表5に示すようにした以外は実施例19と同様にして、硬化性組成物を調製し、評価サンプルを作製した。評価サンプルの評価結果を表5に示した。ただし、比較例13では硬化膜を形成できなかったため、評価を行わなかった。
硬化性組成物に配合する成分の種類と配合量(部)を表5に示すようにした以外は実施例1と同様にして、硬化性組成物を調製した。
得られた硬化性組成物を、厚さ5mmのガラス板の上に、硬化後の厚さが0.7μmとなるようにスプレー塗工した後、予め60℃に加熱した熱風乾燥機中で120秒間加熱して塗膜を乾燥(溶剤を揮発)させた。次いで、乾燥後の塗膜に対し、空気雰囲気中で、高圧水銀灯(アイグラフィック製、USX5-0902)を用いて1000mJ/cm2(波長340~380nmにおける積算照射量を、紫外線光量計UV-351(オーク製作所製)を用いて測定)の紫外線を照射して塗膜を硬化させ、ガラス板上に硬化膜が積層された積層体を得た。評価サンプルの評価結果を表5に示した。
一方、比較例1の組成物は、滑水性を付与する共重合体を含まず、硬化膜表面が親水性であるため、表2に示すように、滑水性の判定が不可能であった。
比較例2の組成物は、成分(B)を含まないため、表2に示すように、硬化膜の外観が低位であった。また、硬化膜の硬度が低位であった。
比較例3の組成物は、滑水性を付与する成分であるポリジメチルシロキサンユニットを含まない共重合体を用いたため、表2に示すように、滑水性が低位であった。
比較例4の組成物は、滑水性を付与する成分であるポリジメチルシロキサンユニットの含量が少ない共重合体を用いたため、表2に示すように、滑水性が低位であった。
比較例5の組成物は、共重合体(A-1)の構成成分を共重合せずにモノマーのまま添加したため、液状態での相溶性が低位であり、表2に示すように、硬化膜として成形できなかった。
一方、比較例6の積層体は、成分(B)を有さないため、表4に示すように、外観が低位であった。また、硬化性も劣っており、塗膜強度が悪く、硬化膜としての機能を有しないものであった。
比較例7の積層体は、共重合体(A)を有さないため、表4に示すように、滑水性に劣っていた。
比較例8の積層体は、滑水性を付与する成分であるポリジメチルシロキサンユニットを含まない共重合体を用いたため、表4に示すように、滑水性が低位であった。
比較例9の積層体は、滑水性を付与する成分であるポリジメチルシロキサンユニットの含量が少ない共重合体を用いたため、表4に示すように、滑水性及び外観が低位であった。
一方、比較例10の硬化膜は、滑水性を付与する共重合体を含まず、硬化膜表面が親水性であるため、表5に示すように、滑水性の判定が不可能であった。
比較例11の硬化膜は、成分(B)を含まないため、表5に示すように、外観が低位であった。また、硬化性も劣っており、塗膜強度が悪く、硬化膜としての機能を有しないものであった。
比較例12の硬化膜は、滑水性を付与する成分であるポリアルキルシロキサンユニットを含まない共重合体を用いたため、表5に示すように、滑水性が低位であった。
比較例13では、共重合体(A-1)の構成成分を共重合せずにモノマーのまま硬化性組成物に添加したため、表5に示すように、液状態での相溶性が低位であり、硬化膜として成形できなかった。
Claims (19)
- ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)とを含み、
前記共重合体(A)を構成する全構成単位の合計質量に対し、前記シリコーンマクロモノマー(X)に基づく構成単位の割合と前記単量体(Y)に基づく構成単位の割合の合計が55質量%以上である、樹脂組成物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。 - 前記成分(B)が、少なくとも1種の下記式(b)で表されるシラン化合物又はその部分加水分解縮合物からなる、請求項1に記載の樹脂組成物。
R4 4-nSi(OR5)n ・・・(b)
ただし、R4は水素原子、アルキル基、アリール基又はアラルキル基を表し、R5はアルキル基又はフェニル基を表し、nは2~4の整数を表し、n個のOR5は互いに異なっていてもよく、nが2の場合、(4-n)個のR4は互いに異なっていてもよい。 - 前記シリコーンマクロモノマー(X)の重量平均分子量が500~40000である、請求項1又は2に記載の樹脂組成物。
- 前記共重合体(A)を構成する全構成単位の合計質量に対し、前記シリコーンマクロモノマー(X)に基づく構成単位の割合が15~60質量%であり、前記単量体(Y)に基づく構成単位の割合が40~85質量%である、請求項1~3のいずれか一項に記載の樹脂組成物。
- 前記共重合体(A)の重量平均分子量が3000~400000である、請求項1~4のいずれか一項に記載の樹脂組成物。
- 前記成分(B)の重量平均分子量が500以上である、請求項1~5のいずれか一項に記載の樹脂組成物。
- 前記成分(B)がテトラアルコキシシランの部分加水分解縮合物である、請求項1~6のいずれか一項に記載の樹脂組成物。
- 前記成分(B)が、少なくとも1種の前記シラン化合物の部分加水分解縮合物であって重量平均分子量が300~3000である部分加水分解縮合物を、さらに触媒の存在下に加水分解縮合反応させた二次反応物である、請求項1~7のいずれか一項に記載の樹脂組成物。
- さらに開始剤(C)を含む、請求項1~8のいずれか一項に記載の樹脂組成物。
- 前記開始剤(C)が光重合開始剤である、請求項9に記載の樹脂組成物。
- 前記開始剤(C)が、光酸発生剤及び光塩基発生剤からなる群から選ばれる少なくとも1種を含む、請求項9又は10に記載の樹脂組成物。
- センシング部材用途に用いられる、請求項1~11のいずれか一項に記載の樹脂組成物。
- 請求項1~12のいずれか一項に記載の樹脂組成物の硬化物。
- ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)を含み、
槽内温度50℃、槽内湿度99%RH以上の条件にて96時間の耐久性試験を実施した後に、傾斜角を1°ずつ断続的に変化させる断続傾斜により基材を傾けて測定される23℃、20μLの蒸留水の滑落角が60°以下である表面を有する、硬化物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。 - 基材と、請求項14に記載の硬化物からなる層を有する積層体。
- 基材の上に設けられたプライマー層と、前記プライマー層の上に設けられた請求項14に記載の硬化物からなる層とを有する積層体。
- ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)と、光重合開始剤とを含む、樹脂組成物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。 - ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物からなる成分(B)と、光重合開始剤とを含む、硬化物。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。 - ポリアルキルシロキサンユニットを含むシリコーンマクロモノマー(X)に基づく構成単位及び下記式(1)で表される基を有する単量体(Y)に基づく構成単位を含む共重合体(A)と、シラン化合物又はその部分加水分解縮合物を含む成分(B)とを含む樹脂組成物を、加熱処理又は活性エネルギー線照射により硬化させる、硬化物の製造方法。
-R1-M(R2)r(OR3)m-r ・・・(1)
ただし、MはAl、Fe、In、Ge、Hf、Si、Ti、Sn、Zr、又はTaを表し、R1は炭素数1~5の炭化水素基を表し、R2は炭素数1~5のアルキル基、炭素数2~5のアルケニル基、又はアリール基を表し、R3は水素原子、炭素数1~5のアルキル基、炭素数2~5のアルケニル基、アリール基、又はアシル基を表し、mはMに応じた3~4の整数を表し、rは0~3の整数を表し、rが2以上の場合、r個のR2は互いに異なっていてもよく、m-rが2以上の場合、(m-r)個のOR3は互いに異なっていてもよい。
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