JP4877468B2 - Photocurable moisture-proof coating agent composition - Google Patents
Photocurable moisture-proof coating agent composition Download PDFInfo
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- JP4877468B2 JP4877468B2 JP2005240759A JP2005240759A JP4877468B2 JP 4877468 B2 JP4877468 B2 JP 4877468B2 JP 2005240759 A JP2005240759 A JP 2005240759A JP 2005240759 A JP2005240759 A JP 2005240759A JP 4877468 B2 JP4877468 B2 JP 4877468B2
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- acrylate
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- proof coating
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- 239000000203 mixture Substances 0.000 title claims description 20
- 239000011248 coating agent Substances 0.000 title claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 47
- -1 isostearyl Chemical group 0.000 claims description 26
- 239000000843 powder Substances 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 4
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 claims description 2
- 150000008062 acetophenones Chemical class 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 2
- BXCOOPLIKAAONJ-UHFFFAOYSA-N di(propan-2-yl)diazene Chemical compound CC(C)N=NC(C)C BXCOOPLIKAAONJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- YYWLHHUMIIIZDH-UHFFFAOYSA-N s-benzoylsulfanyl benzenecarbothioate Chemical compound C=1C=CC=CC=1C(=O)SSC(=O)C1=CC=CC=C1 YYWLHHUMIIIZDH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 claims 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000463 material Substances 0.000 description 19
- 239000004698 Polyethylene Substances 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 2
- 239000005042 ethylene-ethyl acrylate Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 2
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- QLZJUIZVJLSNDD-UHFFFAOYSA-N 2-(2-methylidenebutanoyloxy)ethyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OCCOC(=O)C(=C)CC QLZJUIZVJLSNDD-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Paints Or Removers (AREA)
Description
本発明は、光硬化性の防湿コート剤組成物に関するものであり、特にコーティングされる被着体が難接着材質であっても密着性、接着性がよく湿分を透過させず、かつ、難接着材質だけでなく金属等にも密着性、接着性が良い防湿コート剤組成物に関するものである。 The present invention relates to a photocurable moisture-proof coating agent composition, and in particular, even if an adherend to be coated is a difficult-to-adhere material, it has good adhesion and adhesiveness, does not transmit moisture, and is difficult. The present invention relates to a moisture-proof coating composition having good adhesion and adhesion to not only adhesive materials but also metals.
有機ＥＬ素子や、電池など内部に湿分（水分）が透過するとその性能が低下するものが数多く存在する。それらは湿分を透過させないように有機樹脂などでコートティングすることが提案されている。そのコート剤として、アクリル樹脂、シリコーン樹脂、エポキシ樹脂等が使用されている。その中でも（メタ）アクリレートを主成分とした光硬化性（メタ）アクリレート樹脂は施工が容易であり有用である。 There are many organic EL elements, batteries, and the like whose performance deteriorates when moisture (moisture) permeates inside. It has been proposed that they are coated with an organic resin or the like so as not to allow moisture to permeate. As the coating agent, acrylic resin, silicone resin, epoxy resin and the like are used. Among them, a photocurable (meth) acrylate resin mainly composed of (meth) acrylate is easy to construct and useful.
光硬化性を有する（メタ）アクリレート樹脂は、その多種の構造より柔軟な硬化物から高硬度を有する硬化物を有するものまで、さまざまな性能を有し、現在産業的利用価値の非常に高い物質であり、様々な組成物が提案され、商品としても多種販売されている。しかしながら、（メタ）アクリレート樹脂は難接着物といわれるシリコーンゴムやポリオレフィン系の難接着材質に対して密着性、接着性が悪い。 Photo-curing (meth) acrylate resins have a variety of performances, ranging from flexible cured products to those having a high hardness from various types of structures, and are currently highly industrially useful. Therefore, various compositions have been proposed and various products are sold. However, the (meth) acrylate resin has poor adhesion and adhesion to silicone rubber and polyolefin-based difficult-to-bond materials, which are called difficult-to-bond materials.
従来、（メタ）アクリレート樹脂を難接着材質に密着、接着する際は、予め、被着体である難接着材質の被着面にコロナ放電やプラズマなどの熱的、電気的処理を施して祖面化し接触表面積を増加させたり、投錨効果を付与させる方法や、難接着材質の被着面に強酸などの化学的処理で被着体表面に極性基を付与させるという方法が提案されている。また、難接着材質の表面を物理的、化学的に改質するのではなく、特許文献１〜２に開示されているようにプライマーをあらかじめ塗布することにより難接着材質への密着性、接着性を向上させる方法も開示されている。
しかしながら、上述の方法は接着工程に先立って予め表面処理工程やプライマー塗布工程が必要であり作業が繁雑である。さらに、電気的処理を施すにあたっては、大型で高価な設備が必要であり、コストが大きくかかるという問題があった。また化学処理により極性基を付与するにあたっては処理時間が長くなる、安全性が低い、廃液の処理などの問題があった。 However, the above-described method requires a surface treatment step and a primer coating step in advance of the bonding step, and the work is complicated. Furthermore, in performing the electrical treatment, there is a problem that a large and expensive facility is required, and the cost is high. In addition, when a polar group is added by chemical treatment, there are problems such as a long treatment time, low safety, and waste liquid treatment.
（メタ）アクリレート樹脂以外にも防湿コート剤としてエポキシ樹脂やシリコーン樹脂が使用されているが、どれも、難接着物質への密着性、接着性が悪いものであった。密着性、接着性が悪いと接着界面からの湿気を遮断することができずに防湿性に対する信頼性が低い。よって、難接着材質への防湿性能は不十分なものであった。また、密着性、接着性の不足だけでなく、樹脂そのものの透湿性により、被コーティング物質に湿分が透過してしまうという問題もある。従来の組成物では湿分の透過性が高く、防湿コート剤として用いることは不十分なものであった。 In addition to the (meth) acrylate resin, an epoxy resin or a silicone resin is used as a moisture-proof coating agent, but all have poor adhesion and adhesion to difficult-to-adhere substances. If the adhesion and adhesion are poor, moisture from the adhesion interface cannot be blocked and the reliability with respect to moisture resistance is low. Therefore, the moisture-proof performance to a difficult-to-adhere material was insufficient. In addition to the lack of adhesion and adhesion, there is also a problem that moisture permeates the material to be coated due to the moisture permeability of the resin itself. Conventional compositions have high moisture permeability and are insufficient for use as moisture-proof coating agents.
一方、光硬化性樹脂組成物で熱可塑性エラストマーを含有するものはすでに公知である。たとえば、特許文献３、４には（メタ）アクリレートに熱可塑性エラストマーと光開始剤を添加する接着剤または充填用組成物が開示されている。特許文献３は可撓性を持たせることを主の目的としており、難接着物質へ密着性を向上させるという課題は述べられていない。また、特許文献４はＩＣカードなどの貼合せおよびＩＣチップの充填に適した組成物であり、ＩＣカードの基材の材質としてポリエステル系樹脂が例示されている。しかし、シリコーン樹脂やポリエチレン樹脂などの難接着材質に対して、密着性、接着性は満足できるものではなかった。
本発明は上記課題を解決するために鋭意検討したものであり、被コーティング部材を表面処理などの煩雑な工程を必要とせず優れた密着性、接着性を示し、優れた防湿性能を示すコート剤組成物を提供することを目的とするものである。 The present invention has been intensively studied in order to solve the above-mentioned problems. A coating agent that exhibits excellent adhesion and adhesiveness without requiring a complicated process such as surface treatment of a member to be coated and exhibits excellent moisture-proof performance. The object is to provide a composition.
すなわち、本発明は（ａ）無水マレイン酸変性のＳＥＢＳ共重合体、（ｂ）ＳＩＢＳ共重合体及び無水マレイン酸変性されていないＳＥＢＳ共重合体からなる群から１以上選択される熱可塑性エラストマー、（ｃ）炭素数１８〜２５の鎖状脂肪族単官能（メタ）アクリレート、（ｄ）光開始剤、（ｅ）充填材を含む光硬化性防湿コート剤組成物において、前記（ａ）成分と（ｂ）成分の配合比が（ａ）：（ｂ）＝１：３〜３：１であり、
且つ、前記（ｃ）成分がｎ−ステアリル（メタ）アクリレート、イソステアリル（メタ）アクリレート、ｎ−オクタデシル（メタ）アクリレート、イソオクタデシル（メタ）アクリレート、ノナデカシル（メタ）アクリレート、イソノナデシル（メタ）アクリレート、エイコシル（メタ）アクリレート、ペンタコシル（メタ）アクリレート及び３−オクチルデシル−１−（メタ）アクリレートからなる群から１以上選択され、且つ、前記（ｅ）成分がポリスチレン粉，シリカ粉、アルミナ粉、ガラス粉、タルク粉、炭酸カルシウム粉、クレー及びマイカからなる群から１以上選択されることを特徴とする光硬化性防湿コート剤組成物である。
That is, the present invention comprises (a) a maleic anhydride-modified SEBS copolymer, (b) one or more thermoplastic elastomers selected from the group consisting of a SIBS copolymer and a maleic anhydride-unmodified SEBS copolymer , (C) A photocurable moisture-proof coating agent composition comprising a chain aliphatic monofunctional (meth) acrylate having 18 to 25 carbon atoms, (d) a photoinitiator, and (e) a filler. (B) The compounding ratio of the components is (a) :( b) = 1: 3 to 3: 1,
And said (c) component is n-stearyl (meth) acrylate, isostearyl (meth) acrylate, n-octadecyl (meth) acrylate, isooctadecyl (meth) acrylate, nonadecacil (meth) acrylate, isononadecyl (meth) acrylate, One or more selected from the group consisting of eicosyl (meth) acrylate, pentacosyl (meth) acrylate and 3-octyldecyl-1- (meth) acrylate, and the component (e) is polystyrene powder, silica powder, alumina powder, glass One or more selected from the group consisting of powder, talc powder, calcium carbonate powder, clay and mica .
以下、本発明を具体的に詳述する。本発明に用いられる（ａ）成分は無水マレイン酸変性のＳＥＢＳ共重合体である。（ａ）成分はスチレン−エチレン−ブチレン−スチレン共重合体の構造において、中間ブロックのＥＢを無水マレイン酸で変性したトリブロックコポリマーである。このような成分はクレイトンＦＧ １９０１Ｘ、クレイトンＦＧ１９２４Ｘ（シェル化学社製）として市販されている。 Hereinafter, the present invention will be described in detail. The component (a) used in the present invention is a maleic anhydride-modified SEBS copolymer. Component (a) is a triblock copolymer obtained by modifying EB of the intermediate block with maleic anhydride in the structure of a styrene-ethylene-butylene-styrene copolymer. Such components are commercially available as Clayton FG 1901X and Clayton FG1924X (manufactured by Shell Chemical Co., Ltd.).
本発明の（ｂ）成分は熱可塑性エラストマーである。本成分は以下のものが例示される。スチレン−ブタジエンブロック共重合体（ＳＢ）、スチレン−エチレン／プロピレンブロック共重合体（ＳＥＰ）、スチレン−エチレン／ブチレンブロック共重合体（ＳＥＢ）、スチレン−ブタジエン−スチレンブロック共重合体（ＳＢＳ）、スチレン−イソプレン−スチレンブロック共重合体（ＳＩＳ）、スチレン−エチレン／ブチレン−スチレンブロック共重合体（ＳＥＢＳ）、スチレンーエチレン／プロピレン−スチレンブロック共重合体（ＳＥＰＳ）、エチレン−酢酸ビニルブロック共重合体（ＥＶＡ）、エチレン−エチルアクリレートブロック共重合体（ＥＥＡ）等があげられる。この中で特に好ましい例としては、ＳＥＢＳ、ＳＩＢＳがあげられる。これらの熱可塑性エラストマーは単独で使用することはもちろん、複合して使用することもできる。無水マレイン酸変性スチレン−エチレン／ブチレン−スチレンブロック共重合体（ＳＥＢＳ）も分類的には（ｂ）成分に分類されるが、（ｂ）成分からは除外される。すなわち、（ａ）成分の無水マレイン酸変性ＳＥＢＳ共重合体と（ａ）成分でない熱可塑性エラストマーが共存しなければならない。 The component (b) of the present invention is a thermoplastic elastomer. This component is exemplified as follows. Styrene-butadiene block copolymer (SB), styrene-ethylene / propylene block copolymer (SEP), styrene-ethylene / butylene block copolymer (SEB), styrene-butadiene-styrene block copolymer (SBS), Styrene-isoprene-styrene block copolymer (SIS), styrene-ethylene / butylene-styrene block copolymer (SEBS), styrene-ethylene / propylene-styrene block copolymer (SEPS), ethylene-vinyl acetate block copolymer Examples thereof include a combination (EVA) and an ethylene-ethyl acrylate block copolymer (EEA). Among these, SEBS and SIBS are particularly preferable examples. These thermoplastic elastomers can be used alone or in combination. Maleic anhydride-modified styrene-ethylene / butylene-styrene block copolymer (SEBS) is also classified as component (b), but is excluded from component (b). That is, the maleic anhydride-modified SEBS copolymer as the component (a) and the thermoplastic elastomer that is not the component (a) must coexist.
（ｂ）成分の添加量は（ａ）成分との成分比で（ａ）：（ｂ）＝１：３〜３：１程度である。 The amount of component (b) added is about (a) :( b) = 1: 3 to 3: 1 in terms of the component ratio to component (a).
本発明の（ｃ）成分は炭素数１８〜２５の鎖状脂肪族単官能（メタ）アクリレートである。（ｃ）成分は、炭素数が１８〜２５の鎖状脂肪族にアクリロイル基またはメタクリロイル基を１つ含有するものであり、炭素数はあまり大きいと組成物の粘度が高くなり、反応性が低下するので、炭素数は２５までが使用できる。炭素数が１７以下だと難接着材質に対する接着性が低くなり、防湿コート剤としての信頼性が低下する。また、鎖状脂肪族部分はすべて直鎖でなくても側鎖を有する構造でもよい。このような成分としてｎ−ステアリル（メタ）アクリレート、イソステアリル（メタ）アクリレート、ｎ−オクタデシル（メタ）アクリレート、イソオクタデシル（メタ）アクリレート、ノナデカシル（メタ）アクリレート、イソノナデシル（メタ）アクリレート、エイコシル（メタ）アクリレート、ペンタコシル（メタ）アクリレート、３−オクチルデシル−１−（メタ）アクリレート等が例示される。 The component (c) of the present invention is a chain aliphatic monofunctional (meth) acrylate having 18 to 25 carbon atoms. The component (c) contains one acryloyl group or methacryloyl group in a chain aliphatic group having 18 to 25 carbon atoms. If the carbon number is too large, the viscosity of the composition increases and the reactivity decreases. Therefore, up to 25 carbon atoms can be used. When the number of carbon atoms is 17 or less, the adhesiveness to difficult-to-adhere materials is lowered, and the reliability as a moisture-proof coating agent is lowered. Further, the chain-like aliphatic moiety may not be all linear but may have a structure having a side chain. As such components, n-stearyl (meth) acrylate, isostearyl (meth) acrylate, n-octadecyl (meth) acrylate, isooctadecyl (meth) acrylate, nonadecyl (meth) acrylate, isononadecyl (meth) acrylate, eicosyl (meta) ) Acrylate, pentacosyl (meth) acrylate, 3-octyldecyl-1- (meth) acrylate and the like.
本発明における（ｃ）成分の添加量は（ａ）成分と（ｂ）成分の合計量で、（ｃ）成分：（ａ）＋（ｂ）成分＝４０：６０〜９５：５の範囲が好ましい。 The added amount of the component (c) in the present invention is the total amount of the component (a) and the component (b), and the range of (c) component: (a) + (b) component = 40: 60 to 95: 5 is preferable. .
さらに、本発明の希釈剤として本発明の目的を損なわない範囲で（メタ）アクリルモノマーを用いることもできる。具体的な例として２−エチルヘキシル（メタ）アクリレート、オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、ラウリル（メタ）アクリレート、デシル（メタ）アクリレート、ドデシル（メタ）アクリレート、ステアリル（メタ）アクリレート、ヘキサデシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、テトラヒドロフルフリル（メタ）アクリレート、フノキシエチル（メタ）アクリレート、イソアミル（メタ）アクリレート、エトキシジエチレングリコール（メタ）アクリレート、メトキシトリエチレングリコール（メタ）アクリレート等があげられる。 Furthermore, a (meth) acryl monomer can also be used as a diluent of the present invention as long as the object of the present invention is not impaired. Specific examples include 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, stearyl (meth) acrylate, hexadecyl (Meth) acrylate, isobornyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxyethyl (meth) acrylate, isoamyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, etc. .
本発明の（ｄ）成分の光開始剤は、特に限定されず、公知のものでよい。例えば、２，２−ジメトキシ−２−フェニルアセトフェノン、２，２−ジエトキシアセトフェノン、塩素化アセトフェノン、２−メチル−１−（４−メチルチオフェニル）−２−モルホリノ−プロパン−１−オン等のアセトフェノン類、ベンゾフェノン類、ベンジル、メチルオルソベンゾイルベンゾエート、ベンゾインアルキルエーテル等のベンゾイン類、α，α’−アゾビスイソブチロニトリル、２，２’−アゾビスプロパン、ヒドラゾン等のアゾ化合物、 ベンゾイルパーオキサイド、ジターシャリーブチルパーオキサイド等の有機パーオキサイド類、ジフェニルジサルファイド、ジベンジルジサルファイド、ジベンゾイルジサルファイド等のジフェニルジサルファイド類等が挙げられる。また、イルガキュアー１８４（チバガイギー製、１−ヒドロキシシクロヘキシルフェニルケトン）等の市販の光開始剤も使用できる。またこれらの光開始剤は単独で使用することはもちろん、複合して使用することもできる。（ｄ）成分の添加量は（ａ）（ｂ）（ｃ）成分の合計量１００重量部に対して０．０１〜１０重量部の範囲であり、さらには０．１〜５重量部であることが好ましい。 The photoinitiator of the component (d) of the present invention is not particularly limited and may be a known one. For example, acetophenone such as 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, chlorinated acetophenone, 2-methyl-1- (4-methylthiophenyl) -2-morpholino-propan-1-one Benzoins, benzophenones, benzoins such as benzyl, methyl orthobenzoylbenzoate, benzoin alkyl ether, azo compounds such as α, α'-azobisisobutyronitrile, 2,2'-azobispropane, hydrazone, benzoyl peroxide And organic peroxides such as ditertiary butyl peroxide, and diphenyl disulfides such as diphenyl disulfide, dibenzyl disulfide, and dibenzoyl disulfide. Commercially available photoinitiators such as Irgacure 184 (manufactured by Ciba Geigy, 1-hydroxycyclohexyl phenyl ketone) can also be used. These photoinitiators can be used alone or in combination. The amount of component (d) added is in the range of 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, relative to 100 parts by weight of the total amount of components (a), (b) and (c). It is preferable.
本発明（ｅ）成分は充填剤であり、以下にあげられる成分である。ポリスチレン粉，シリカ粉、アルミナ粉、ガラス粉、タルク粉、炭酸カルシウム粉、クレー、マイカがあげられるが、これらの充填剤は単独で使用することはもちろん、複合して使用することもできる。この中で特に好ましい例としては、シリカ粉、ガラス粉があげられる。（ｅ）成分の添加量は（ａ）（ｂ）（ｃ）成分の合計量１００重量部に対して０．１〜７０重量部であり、好ましくは５〜５０重量部である。 The component (e) of the present invention is a filler and includes the following components. Polystyrene powder, silica powder, alumina powder, glass powder, talc powder, calcium carbonate powder, clay, and mica can be used. These fillers can be used alone or in combination. Among these, silica powder and glass powder are particularly preferable examples. Component (e) is added in an amount of 0.1 to 70 parts by weight, preferably 5 to 50 parts by weight, based on 100 parts by weight of the total amount of components (a), (b) and (c).
また、本発明の組成物に、本発明の目的を損なわない範囲で各種添加剤を添加しても良い。例えばフェノール系やリン系，チオール系等の酸化防止剤，さらに、本発明の組成物には防黴剤、難燃剤、可塑剤、チクソ性付与剤、接着付与剤、硬化促進剤、顔料などを添加することができる。 Moreover, you may add various additives to the composition of this invention in the range which does not impair the objective of this invention. For example, phenol-based, phosphorus-based, thiol-based antioxidants, and the composition of the present invention further includes an antifungal agent, a flame retardant, a plasticizer, a thixotropic agent, an adhesion-imparting agent, a curing accelerator, a pigment, and the like. Can be added.
本発明の光硬化性の防湿コート剤組成物は難接着材質に対して優れた密着性、接着性を示し、さらに防湿性に優れるものである。特にシリコーンゴム、ＥＰＤＭゴム、軟質塩化ビニル、ポリプロピレン（ＰＰ）、ポリエチレン（ＰＥ）、ポリアセタール、ポリエチレンテレフタレート（ＰＥＴ）、ポリブチレンテレフタレート（ＰＢＴ）、ポリプロピレンサルファイト（ＰＰＳ）、ポリスチレン（ＰＳ）、ポリイミド（ＰＩ）などの難接着材質に対して優れた密着性、接着性が発現する。また、難接着物質だけでなく、金属に対しても優れた密着性、接着性を発現する。よって、ＥＬ素子や電池のパッキンなどの防湿を必要とする箇所の防湿コート剤として有用である。 The photocurable moisture-proof coating agent composition of the present invention exhibits excellent adhesion and adhesion to difficult-to-adhere materials, and further has excellent moisture resistance. Silicone rubber, EPDM rubber, soft vinyl chloride, polypropylene (PP), polyethylene (PE), polyacetal, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene sulfite (PPS), polystyrene (PS), polyimide ( Excellent adhesion and adhesion to difficult-to-bond materials such as PI). In addition, it exhibits excellent adhesion and adhesion not only to difficult-to-adhere substances but also to metals. Therefore, it is useful as a moisture-proof coating agent in places requiring moisture-proof such as EL elements and battery packing.
以下、実施例により本発明を具体的に詳述するが、本発明はこれら実施例によって権利範囲が制限されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely in detail, this invention does not restrict | limit the right range by these Examples.
表１の記載の通りコート剤組成物を配合した。ただし、表中、光開始剤は２−ヒドロキシ−２−メチル−１−フェニル−プロパン−１−オンを使用した。 A coating composition was blended as described in Table 1. However, in the table, 2-hydroxy-2-methyl-1-phenyl-propan-1-one was used as the photoinitiator.
これら各組成物を用いて難接着性材料と金属の接着強度を測定した。試験は次のようにして行った。縦１５ｃｍ、横２．５ｃｍ、厚み２．０ｍｍのポリエチレン（ＰＥ）試験片と縦１５ｃｍ、横２．５ｃｍ、厚み１．６ｍｍのＳＵＳ４０３を使用し、この試験片に接着剤を塗布し、接着層が縦１．０ｃｍ，横２．５ｃｍになるように試験片を貼り合わせ、ＰＥ側から照射量３０００ｍＪ／ｃｍ２の紫外線を照射して組成物を硬化させ、試験片を接着した。接着された試験片を引っ張り試験機（ＯＲＩＥＮＴＥＣ）を用いて引張せん断接着強さ試験を行い、ＰＥとＳＵＳ４３０に対する接着性の結果を表１に示した。 Using each of these compositions, the adhesive strength between the hardly adhesive material and the metal was measured. The test was conducted as follows. A polyethylene (PE) test piece having a length of 15 cm, a width of 2.5 cm, and a thickness of 2.0 mm and SUS403 having a length of 15 cm, a width of 2.5 cm, and a thickness of 1.6 mm were used. The test pieces were bonded so that the length was 1.0 cm and the width was 2.5 cm, and the composition was cured by irradiating ultraviolet rays with an irradiation amount of 3000 mJ / cm 2 from the PE side, and the test pieces were adhered. The bonded specimen was subjected to a tensile shear bond strength test using a tensile tester (ORIENTEC), and the results of adhesion to PE and SUS430 are shown in Table 1.
また、ＪＩＳ−Ｚ−０２０８に従い、カップ法を用いて４０℃９５％の環境下で各組成物の透湿性試験を行いた。その結果を表１に示した。 Moreover, according to JIS-Z-0208, the moisture permeability test of each composition was done in 40 degreeC95% environment using the cup method. The results are shown in Table 1.
本発明の光硬化性防湿コート剤組成物は湿気を遮断すべき物質、すなわち、ＥＬ素子、電池、電子部品などに利用可能である。
The photocurable moisture-proof coating agent composition of the present invention can be used for substances that should block moisture, that is, EL elements, batteries, electronic components, and the like.
Claims (3)
前記（ａ）成分と（ｂ）成分の配合比が（ａ）：（ｂ）＝１：３〜３：１であり、
且つ、前記（ｃ）成分がｎ−ステアリル（メタ）アクリレート、イソステアリル（メタ）アクリレート、ｎ−オクタデシル（メタ）アクリレート、イソオクタデシル（メタ）アクリレート、ノナデカシル（メタ）アクリレート、イソノナデシル（メタ）アクリレート、エイコシル（メタ）アクリレート、ペンタコシル（メタ）アクリレート及び３−オクチルデシル−１−（メタ）アクリレートからなる群から１以上選択され、
且つ、前記（ｅ）成分がポリスチレン粉，シリカ粉、アルミナ粉、ガラス粉、タルク粉、炭酸カルシウム粉、クレー及びマイカからなる群から１以上選択されることを特徴とする光硬化性防湿コート剤組成物。 (A) a maleic anhydride modified SEBS copolymer, (b) one or more thermoplastic elastomers selected from the group consisting of a SIBS copolymer and a maleic anhydride unmodified SEBS copolymer , (c) carbon number In a photocurable moisture-proof coating composition comprising 18 to 25 chain aliphatic monofunctional (meth) acrylate, (d) a photoinitiator, and (e) a filler ,
The blending ratio of the component (a) and the component (b) is (a) :( b) = 1: 3 to 3: 1,
And said (c) component is n-stearyl (meth) acrylate, isostearyl (meth) acrylate, n-octadecyl (meth) acrylate, isooctadecyl (meth) acrylate, nonadecacil (meth) acrylate, isononadecyl (meth) acrylate, One or more selected from the group consisting of eicosyl (meth) acrylate, pentacosyl (meth) acrylate and 3-octyldecyl-1- (meth) acrylate,
The component (e) is selected from the group consisting of polystyrene powder, silica powder, alumina powder, glass powder, talc powder, calcium carbonate powder, clay and mica. Composition.
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