JP2016000766A - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
- Publication number
- JP2016000766A JP2016000766A JP2014120356A JP2014120356A JP2016000766A JP 2016000766 A JP2016000766 A JP 2016000766A JP 2014120356 A JP2014120356 A JP 2014120356A JP 2014120356 A JP2014120356 A JP 2014120356A JP 2016000766 A JP2016000766 A JP 2016000766A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- component
- acrylate
- photocurable composition
- acrylic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 53
- 239000000178 monomer Substances 0.000 claims abstract description 37
- -1 acryl Chemical group 0.000 claims abstract description 24
- 239000000853 adhesive Substances 0.000 claims abstract description 20
- 230000001070 adhesive effect Effects 0.000 claims abstract description 20
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical group C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000009477 glass transition Effects 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 51
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 10
- 239000004734 Polyphenylene sulfide Substances 0.000 abstract description 5
- 229920000069 polyphenylene sulfide Polymers 0.000 abstract description 5
- 229920006351 engineering plastic Polymers 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000945 filler Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IAXXETNIOYFMLW-GYSYKLTISA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C(=C)C)C[C@@H]1C2(C)C IAXXETNIOYFMLW-GYSYKLTISA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 101000720524 Gordonia sp. (strain TY-5) Acetone monooxygenase (methyl acetate-forming) Proteins 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 1
- ZRIPJJWYODJTLH-UHFFFAOYSA-N (4-benzylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 ZRIPJJWYODJTLH-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- HDMHXSCNTJQYOS-UHFFFAOYSA-N 1-(4-prop-2-enylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(CC=C)C=C1 HDMHXSCNTJQYOS-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- LEUJIOLEGDAICX-UHFFFAOYSA-N 3-chloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(Cl)C=C3OC2=C1 LEUJIOLEGDAICX-UHFFFAOYSA-N 0.000 description 1
- KMSYDDGPKBBSNA-UHFFFAOYSA-N 3-ethyl-1-phenylpentan-1-one Chemical compound CCC(CC)CC(=O)C1=CC=CC=C1 KMSYDDGPKBBSNA-UHFFFAOYSA-N 0.000 description 1
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 1
- DLGLWFGFEQRRCP-UHFFFAOYSA-N 6-chloro-1-nonylxanthen-9-one Chemical compound O1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2CCCCCCCCC DLGLWFGFEQRRCP-UHFFFAOYSA-N 0.000 description 1
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-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
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000002904 solvent 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
- 230000035882 stress Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
(A)成分:(メタ)アクリル基を有する(メタ)アクリルモノマー重合体
(B)成分:アクリロイルモルホリン
(C)成分:ジシクロペンタニル(メタ)アクリレート
(D)成分:光開始剤
組成物を調製するために下記成分を準備した。
(A)成分:(メタ)アクリル基を有する(メタ)アクリルモノマー重合体
・両末端にアクリル基を有するポリアクリルモノマー重合体(RC200C 株式会社カネカ製)
(A’)成分:(A)成分以外の(メタ)アクリル基を有する化合物
・ポリブタジエンの両末端にウレタン結合を介してアクリル基を有する樹脂(TE−2000 日本曹達株式会社製)
・エステルタイプの2官能アクリルオリゴマー(UV−3000B 日本合成化学工業株式会社製)
(B)成分:アクリロイルモルホリン
・アクリロイルモルホリン(ACMO 興人フィルム&ケミカルズ株式会社製)
(C)成分:ジシクロペンタニル(メタ)アクリレート
・ジシクロペンタニルアクリレ−ト(FA−513AS 日立化成株式会社製)
(C)成分以外の(メタ)アクリレート
脂環式炭化水素基を有する単官能(メタ)アクリルモノマー
・イソボルニルメタクリレート(ライトエステルIB−X 共栄社化学株式会社製)
芳香族構造を有する単官能(メタ)アクリルモノマー
・フェノキシエチルアクリレート(V#192 大阪有機化学工業株式会社製)
炭素数10以下のアルキル基を有する単官能(メタ)アクリレート
・イソノニルアクリレート(INAA 大阪有機化学工業株式会社製)
その他の(メタ)アクリレート
・イソステアリルアクリレート(S−1800A 新中村化学工業株式会社製)
・ジメチロールトリシクロデカンジアクリレート(ライトアクリレートDPM−A 共栄社化学株式会社製)
(D)成分:光開始剤
・2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン(DAROCUR1173 BASF社製)
添加剤
・2−ヒドロキシエチルメタクリレートアシッドホスフェート(JPA−514 城北化学工業株式会社製)
充填剤
・シリカ粉(FUSELEX E−1 株式会社龍森製)
ポリフェニレンサルファイド(PPS)製の基材上に、外径7.6mm/内径3.0mmの厚さ0.5mmの金属製ワッシャー(単位:N)を置く。内径を組成物で満たすため、組成物を10mg滴下する。積算光量30kJ/m2で紫外線照射して組成物を光硬化させてテストピースを作成する。室温に戻った後、デジタルフォースゲージのヘッドを50mm/minでスライドさせて、ワッシャー側面から剪断方向にワッシャーをはじいて、「強度(N)」を測定する。内径から換算して「接着力(MPa)」とする。好ましくは4MPa以上であり、より好ましくは6MPa以上である。
前記の接着力測定におけるテストピース作成方法と同様にテストピースを作成する。初期の接着力を測定し、これを「初期接着力」とする。その後、別のテストピースを60℃×95%RHの雰囲気下で、テストピースを144時間放置する。耐湿試験終了後にテストピースを取り出し、テストピースの温度が室温になった後、「接着力(MPa)」を測定した。また、初期の剪断強度からの変化を「変化率(%)」とする。「変化率」は−40〜0%であることが好ましく、さらに好ましくは−30〜0%であり、最も好ましくは−25〜0%である。
組成物の厚さを1mmに設定し、積算光量30kJ/m2を紫外線照射してシート状の硬化物を作成する。幅10mmに打ち抜き、テストピースを作製する。DMA装置に取り付けて−40〜200℃の温度範囲で測定を行う。−20℃における貯蔵弾性率、損失弾性率の極大値(ガラス転移温度)を確認し、それぞれ「E’(×108Pa)」、「E”(℃)」、と表す。耐湿試験において、熱膨張に対する追従と共に吸湿を抑制するためには、E’としては貯蔵弾性率が10.0×108Pa未満であることが好ましい。また、E”としては80℃以上であることが好ましく、100℃以上にあることがさらに好ましい。
Claims (6)
- (A)〜(D)成分を含み、(A)成分100質量部に対して、(B)成分、(C)成分および(C)成分以外の(メタ)アクリルモノマーの合計が50〜200質量部である光硬化性組成物。
(A)成分:(メタ)アクリル基を有する(メタ)アクリルモノマー重合体
(B)成分:アクリロイルモルホリン
(C)成分:ジシクロペンタニル(メタ)アクリレート
(D)成分:光開始剤 - (C)成分以外の脂環式炭化水素基を有する単官能(メタ)アクリルモノマーと、芳香族構造を有する単官能(メタ)アクリルモノマーおよび/または炭素数10以下のアルキル基を有する単官能(メタ)アクリレートを含む請求項1に記載の光硬化性組成物。
- イソボルニル(メタ)アクリレートと、フェノキシエチル(メタ)アクリレートおよび/またはイソノニル(メタ)アクリレートを含む請求項2に記載の光硬化性組成物。
- 硬化物のガラス転移温度が100℃以上である請求項1〜3のいずれか記載の光硬化性組成物。
- 光ピックアップに用いられる請求項1〜4のいずれかに記載の光硬化性組成物。
- 請求項1〜5のいずれかに記載のフォトディテクターの組み立て、レーザーダイオードの組み立てまたはアクチュエーターの固定に用いられる接着剤。
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WO2016181742A1 (ja) * | 2015-05-14 | 2016-11-17 | 株式会社カネカ | ラジカル硬化性組成物およびその硬化物 |
JP2017186439A (ja) * | 2016-04-05 | 2017-10-12 | 株式会社スリーボンド | ラジカル硬化性樹脂組成物、モータ用接着剤組成物 |
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JP2008150502A (ja) * | 2006-12-18 | 2008-07-03 | Kaneka Corp | 硬化性組成物およびその硬化物 |
JP2014162852A (ja) * | 2013-02-25 | 2014-09-08 | Hitachi Chemical Co Ltd | 光硬化型樹脂組成物及びそれを用いた貼り合せシート |
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JPS61133201A (ja) | 1984-11-30 | 1986-06-20 | Sunstar Giken Kk | 室温硬化性弾性組成物 |
JP3605848B2 (ja) * | 1994-05-17 | 2004-12-22 | Jsr株式会社 | 液状硬化性粘・接着剤組成物 |
JP3751753B2 (ja) | 1998-07-23 | 2006-03-01 | 株式会社カネカ | 末端にアルケニル基を有する重合体の製造方法及び該重合体を用いた硬化性組成物 |
JP2001271055A (ja) | 2000-03-27 | 2001-10-02 | Kanegafuchi Chem Ind Co Ltd | シーリング材組成物 |
JP4499260B2 (ja) | 2000-08-25 | 2010-07-07 | 株式会社カネカ | ビニル系重合体の精製方法 |
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JPWO2016181742A1 (ja) * | 2015-05-14 | 2018-03-01 | 株式会社カネカ | ラジカル硬化性組成物およびその硬化物 |
JP2017186439A (ja) * | 2016-04-05 | 2017-10-12 | 株式会社スリーボンド | ラジカル硬化性樹脂組成物、モータ用接着剤組成物 |
JP2020007449A (ja) * | 2018-07-06 | 2020-01-16 | 株式会社コバヤシ | 光硬化性組成物 |
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