CN106715477B - 光固化性树脂组合物 - Google Patents
光固化性树脂组合物 Download PDFInfo
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- CN106715477B CN106715477B CN201580052506.XA CN201580052506A CN106715477B CN 106715477 B CN106715477 B CN 106715477B CN 201580052506 A CN201580052506 A CN 201580052506A CN 106715477 B CN106715477 B CN 106715477B
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- ingredient
- methyl
- resin composition
- photocurable resin
- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 53
- 239000004615 ingredient Substances 0.000 claims abstract description 114
- -1 Tertiary amine compound Chemical class 0.000 claims abstract description 73
- 239000000463 material Substances 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 36
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 29
- 230000003287 optical effect Effects 0.000 claims abstract description 20
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 150000003512 tertiary amines Chemical group 0.000 claims abstract description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 10
- 238000005266 casting Methods 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005410 aryl sulfonium group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 229940043237 diethanolamine Drugs 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- OZICRFXCUVKDRG-UHFFFAOYSA-N 2-[2-hydroxyethyl(propyl)amino]ethanol Chemical compound CCCN(CCO)CCO OZICRFXCUVKDRG-UHFFFAOYSA-N 0.000 claims description 2
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 229940031098 ethanolamine Drugs 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical class CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 2
- MLNKXLRYCLKJSS-RMKNXTFCSA-N (2e)-2-hydroxyimino-1-phenylethanone Chemical compound O\N=C\C(=O)C1=CC=CC=C1 MLNKXLRYCLKJSS-RMKNXTFCSA-N 0.000 claims 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical group OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical class CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 20
- 150000001450 anions Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000011161 development Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 5
- 150000004055 1,2-benzoquinones Chemical class 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 description 3
- NHIAEZJOVSXCRX-UHFFFAOYSA-N C(CCC)S(=O)(=O)O.[F] Chemical compound C(CCC)S(=O)(=O)O.[F] NHIAEZJOVSXCRX-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical class CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 2
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 2
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 125000004386 diacrylate group Chemical group 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
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- 238000000034 method Methods 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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- 150000003141 primary amines Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical class OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- MLBKSHGVUSEVEQ-UHFFFAOYSA-N 1-benzyl-9,10-dimethoxy-3-nitroanthracene-2-sulfonic acid Chemical class [N+](=O)([O-])C=1C(=C(C2=C(C3=CC=CC=C3C(=C2C1)OC)OC)CC1=CC=CC=C1)S(=O)(=O)O MLBKSHGVUSEVEQ-UHFFFAOYSA-N 0.000 description 1
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- IXHBSOXJLNEOPY-UHFFFAOYSA-N 2'-anilino-6'-(n-ethyl-4-methylanilino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C=C(C2(C3=CC=CC=C3C(=O)O2)C2=CC(NC=3C=CC=CC=3)=C(C)C=C2O2)C2=CC=1N(CC)C1=CC=C(C)C=C1 IXHBSOXJLNEOPY-UHFFFAOYSA-N 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
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
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- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
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Abstract
本发明的目的在于提供具有优良的厚膜固化性、并且固化物具有高隐蔽性、进而具有优良的贮藏稳定性的光固化性树脂组合物。本发明为一种光固化性树脂组合物,其含有(A)~(E)成分,(A)成分:无色染料,(B)成分:光致产酸剂,(C)成分:自由基聚合性化合物(不包括具有叔胺骨架的(甲基)丙烯酸酯),(D)成分:光自由基聚合引发剂,(E)成分:叔胺化合物。
Description
技术领域
本发明涉及具有优良的膜厚固化性以及固化物的高隐蔽性、另外具有优良的贮藏稳定性的光固化性树脂组合物。
背景技术
以往,隐蔽性高的光固化性树脂组合物,多用于面向挠性电路板的被覆材料(参考日本特开2013-194156号公报)、试制模型的复制品用铸造材料(参考日本特开平11-060962号公报)、凸状透镜的黑色条纹(参考日本特开2013-082924号公报)、电子设备等的组装用胶粘剂(参考日本特开2014-025021号公报)等。作为对光固化性树脂组合物赋予隐蔽性的代表方法,可以列举出配合作为颜料的碳黑,但在得到隐蔽性的反面,紫外线等活性能量射线的大部分被碳黑吸收,因此颜料的浓度过高时,具有发生固化性不良的问题。
出于这样的背景,在日本特开平11-060962号公报中公开了通过铸造用感光性树脂组合物,固化物为黑色,并且具有优良的厚膜固化性,所述铸造用感光性树脂组合物含有:光自由基聚合引发剂、具有通过酸进行着色的特征的无色染料、光致产酸剂、烯属不饱和化合物。其利用了“通过光照射产生的自由基种”比“通过光照射产生的酸”的产生速度快。即,在利用酸发生黑化前,使光透射至深部而使其固化。
发明内容
然而,为了适用于铸造用树脂,要求优良的厚膜固化性,但日本特开平11-060962号公报中公开的铸造用感光性树脂组合物中,厚膜固化性不充分。
本发明人等鉴于上述课题进行了深入的研究。其结果,完成了涉及光固化性树脂组合物的本发明。以下说明本发明的主旨。本发明的一个实施方式为一种光固化性树脂组合物,其含有(A)~(E)成分,
(A)成分:无色染料、
(B)成分:光致产酸剂、
(C)成分:自由基聚合性化合物(不包括具有叔胺骨架的(甲基)丙烯酸酯)、
(D)成分:光自由基聚合引发剂、
(E)成分:叔胺化合物。
具体实施方式
本发明的一个实施方式为一种光固化性树脂组合物,其含有(A)~(E)成分,
(A)成分:无色染料、
(B)成分:光致产酸剂、
(C)成分:自由基聚合性化合物(不包括具有叔胺骨架的(甲基)丙烯酸酯)、
(D)成分:光自由基聚合引发剂、
(E)成分:叔胺化合物。
通过这样的构成,能够得到具有优良的厚膜固化性、并且固化物具有高隐蔽性的光固化性树脂组合物。另外,上述光固化性树脂可以具有优良的贮藏稳定性。
以下,对本发明的实施方式进行说明。需要说明的是,本发明不仅限于以下的实施方式。
本说明书中,表示范围的“X~Y”是指“X以上且Y以下”,“重量”和“质量”、“重量%”和“质量%”以及“重量份”和“质量份”作为同义词处理。另外,只要没有特别说明,则操作以及物性等的测定是在室温(20~25℃)/相对湿度40~50%的条件下进行测定。需要说明的是,“(甲基)丙烯酸酯”是指“丙烯酸酯”或“甲基丙烯酸酯”。
<(A)成分>
作为本发明的(A)成分的无色染料是通过与酸的接触而发色的化合物,可以对固化物赋予隐蔽性。另外,无色染料可以根据种类发色成黑色、蓝色、绿色、红色等,但从隐蔽性优良的观点出发优选为得到黑色的发色的无色染料。
(A)成分中,作为得到黑色的发色的无色染料,没有特别限定,但例如可以列举出:3-二丁基氨基-6-甲基-7-苯胺基荧烷、3-二丙基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-苯胺基荧烷、3-二甲基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-二甲代苯胺基荧烷、3-(4-二乙基氨基-2-乙氧基苯基)-3-(1-乙基-2-甲基吲哚-3-基)-4-氮杂苯酞等。这些可以使用1种,也可以混合使用二种以上。这些中,从固化物的隐蔽性以及光固化性树脂组合物的厚膜固化性的观点出发,优选为3-二丁基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-苯胺基荧烷。
作为本发明的(A)成分的市售品,没有特别限定,但可以列举出:S-205、BLACK305、ETAC、BLACK100、NIR BLACK78(山田化学工业株式会社制)、ODB、ODB-2、ODB-4、ODB-250、Black-XV(山本化成株式会社制)等。
关于本发明的(A)成分的优选配合量,相对于后述(C)成分100质量份为0.01~20质量份的范围,优选为0.05~10质量份,更优选为0.5~5质量份。(A)成分为0.01质量份以上时,固化物可以具有高隐蔽性。另外,(A)成分为20质量份以下时,光固化性树脂组合物可以具有优良的厚膜固化性。
<(B)成分>
作为本发明的(B)成分的光致产酸剂,是通过活性能量射线的照射产生路易斯酸和布朗斯台德酸等酸的化合物。利用通过上述(B)成分产生的酸能够使作为上述(A)成分的无色染料发色。另外,从能够同时实现隐蔽性以及光固化性树脂组合物的厚膜固化性的观点出发,优选为在365nm以上的波长区域具有吸收的光致产酸剂。另外,作为上述(B)成分,可以大致分为鎓盐系光致产酸剂和非离子性光致产酸剂。
作为本发明中能够使用的鎓盐,没有特别限定,但例如可以列举出:具有六氟锑酸盐阴离子、四氟硼酸盐阴离子、六氟磷酸盐阴离子、由[PR6]-(其中,R各自独立地为氟原子或碳原子数1~12的氟化烷基,至少1个R为碳原子数1~12的氟化烷基)表示的阴离子、由[BR4]-(其中,R各自独立地为氟原子或碳原子数1~12的氟化烷基,至少1个R为碳原子数1~12的氟化烷基)表示的阴离子、由[SbR6]-(其中,R各自独立地为氟原子或碳原子数1~12的氟化烷基,至少1个R为碳原子数1~12的氟化烷基)表示的阴离子、六氯锑酸盐阴离子、三氟甲烷磺酸离子、或氟磺酸离子等平衡阴离子的芳基碘鎓盐、芳基锍盐或芳基重氮鎓盐等。这些可以使用1种,也可以混合使用二种以上。这些中,从固化物的隐蔽性以及光固化性树脂组合物的厚膜固化性的观点出发,优选为具有六氟锑酸盐阴离子、四氟硼酸盐阴离子、六氟磷酸盐阴离子、由[PR6]-表示的阴离子、由[BR4]-表示的阴离子、由[SbR6]-表示的阴离子中的任一种平衡阴离子的芳基锍盐,从对于环境的负荷少的观点出发,更优选为具有四氟硼酸盐阴离子、六氟磷酸盐阴离子、由[PR6]-表示的阴离子、或由[BR4]-表示的阴离子中的任一种平衡阴离子的芳基锍盐,具体而言,可以列举出三芳基锍-六氟磷酸盐等。
作为上述鎓盐系光致产酸剂的市售品,例如,可以列举出:IRGACURE250、IRGACURE270(BASF公司制)、WPI-113、WPI-116、WPI-169、WPI-170、WPI-124、WPAG-638、WPAG-469、WPAG-370、WPAG-367、WPAG-336(和光纯药工业株式会社制)、B2380、B2381、C1390、D2238、D2248、D2253、I0591、T1608、T1609、T2041、T2042(东京化成工业株式会社制)、AT-6992、At-6976(ACETO公司制)、CPI-100、CPI-100P、CPI101A、CPI-200K、CPI-210S(SANAPRO株式会社制)、SP-056、SP-066、SP-130、SP-140、SP-150、SP-170、SP-171、SP-172(ADEKA株式会社制)、CD-1010、CD-1011、CD-1012(Sartomer公司制)、San-Aid SI-60、SI-80、SI-100、SI-60L、SI-80L、SI-100L、SI-L145、SI-L150、SI-L160、SI-L110、SI-L147(三新化学工业株式会社制)、PI2074(Rhodia Japan制)等,但没有特别限定。
作为上述非离子性光致产酸剂,例如,可以列举出:苯酰甲基砜型光致产酸剂、邻硝基苄基酯型光致产酸剂、亚氨基磺酸盐型光致产酸剂、N-羟基酰亚胺的磺酸酯型光致产酸剂等,但不限定于此。这些可以使用1种,也可以混合使用二种以上。作为非离子性光致产酸剂的具体化合物,可以列举出:磺酰基重氮甲烷、肟磺酸酯、酰亚胺磺酸酯、2-硝基苄基磺酸酯、二砜、焦棓酚磺酸酯、对硝基苄基-9,10-二甲氧基蒽-2-磺酸酯、N-磺酰基-苯基磺酰胺、三氟甲烷磺酸-1,8-萘二甲基酰亚胺、九氟丁烷磺酸-1,8-萘二甲基酰亚胺、全氟辛烷磺酸-1、8-萘二甲基酰亚胺、五氟苯磺酸-1,8-萘二甲基酰亚胺、九氟丁烷磺酸-1,3,6-三氧-3,6-二氢-1H-11-硫-氮杂环戊蒽-2-基酯、九氟丁烷磺酸-8-异丙基-1,3,6-三氧-3,6-二氢-1H-11-硫-2-氮杂环戊蒽-2-基酯、1,2-萘醌-2-二叠氮基-5-磺酰氯、1,2-萘醌-2-二叠氮基-4-磺酰氯、1,2-苯醌-2-二叠氮基-4-磺酰氯、1,2-萘醌-2-二叠氮基-5-磺酸钠、1,2-萘醌-2-二叠氮基-4-磺酸钠、1,2-苯醌-2-二叠氮基-4-磺酸钠、1,2-萘醌-2-二叠氮基-5-磺酸钾、1,2-萘醌-2-二叠氮基-4-磺酸钾、1,2-苯醌-2-二叠氮基-4-磺酸钾、1,2-萘醌-2-二叠氮基-5-磺酸甲酯、1,2-苯醌-2-二叠氮基-4-磺酸甲酯等。
作为上述非离子性光致产酸剂的市售品,可以列举出:WPAG-145、WPAG-149、WPAG-170、WPAG-199(和光纯药工业株式会社制)、D2963、F0362、M1209、M1245(东京化成工业株式会社制)、SP-082、SP-103、SP-601、SP-606(ADEKA株式会社制)、SIN-11(株式会社三宝化学研究所制)、NT-1TF(SANAPRO株式会社制)等。
关于本发明的(B)成分的优选配合量,相对于后述(C)成分100质量份为0.01~20质量份的范围,更优选为0.01~10质量份,进一步优选为0.3~10质量份。上述(B)成分为0.01质量份以上时,使作为(A)成分的无色染料发色的效果增大,因此固化物可以具有高隐蔽性。另外,(B)成分为20质量份以下时,固化物可以具有充分的耐热性。另外,从发色性的观点出发,相对于(A)成分1质量份,(B)成分优选为0.1~20质量份。
<(C)成分>
作为本发明的(C)成分的自由基聚合性化合物,可以使用通常用于胶粘剂以及涂料等的具有烯属不饱和基团的化合物,具体而言,可以列举出含有(甲基)丙烯酰基的化合物等。作为上述(C)成分,例如,可以使用单官能性、二官能性、三官能性以及多官能性的单体以及低聚物等。这些可以单独使用,或者也可以作为二种以上的混合物使用。其中,从光固化性以及固化物的物性优良的观点出发,上述(C)成分优选包含低聚物和单体、即包含低聚物和单官能性、二官能性、三官能性以及多官能性的单体中的至少一种。需要说明的是,本发明中具有叔胺骨架的(甲基)丙烯酸酯可以视作后述的(E)成分。
作为上述单官能性单体,例如,可以列举出:丙烯酸、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸叔丁酯、甲基丙烯酸异丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸异癸酯、丁氧基二乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、2-甲基丙烯酰氧基乙基琥珀酸酯、2-甲基丙烯酰氧基乙基六氢邻苯二甲酸、(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸四氢糠酯、己内酯改性(甲基)丙烯酸四氢糠酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸二环戊酯、(甲基)丙烯酸二环戊烯酯、二环戊烯基氧基(甲基)丙烯酸酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基四乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸壬基苯氧基乙酯、(甲基)丙烯酸丁氧基乙酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸4-羟基丁酯、(甲基)丙烯酸甘油酯、(甲基)丙烯酸三氟乙酯、甲基丙烯酰氧基氧基乙基酸式磷酸酯、2-羟基乙基甲基丙烯酸磷酸酯、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-丙烯酰氧基丙基三甲氧基硅烷等。从与本发明的(A)成分以及(B)成分的相溶性以及固化性优良的观点出发,优选为(甲基)丙烯酸环己酯、(甲基)丙烯酸二环戊酯、(甲基)丙烯酸二环戊烯酯、二环戊烯基氧基(甲基)丙烯酸酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸4-羟基丁酯等。
作为上述二官能性单体,例如,可以列举出:乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、四乙二醇二甲基丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、硬脂酸改性季戊四醇二(甲基)丙烯酸酯、二环戊烯基二丙烯酸酯、二(甲基)丙烯酰基异氰脲酸酯、环氧烷烃改性双酚二(甲基)丙烯酸酯、二羟甲基-三环癸烷二丙烯酸酯等。
作为上述三官能性单体,例如可以列举出:三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三(丙烯酰氧基乙基)异氰脲酸酯等。
作为上述多官能性单体,例如,可以列举出:二(三羟甲基丙烷)四(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇单羟基五(甲基)丙烯酸酯、烷基改性二季戊四醇五丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、异氰脲酸EO改性二及三丙烯酸酯等。
这些单官能性、二官能性、三官能性以及多官能性单体可以单独使用,或者可以作为二种以上的混合物使用。
作为上述低聚物,例如,可以列举出:聚丁二烯骨架的氨基甲酸酯(甲基)丙烯酸酯、氢化聚丁二烯骨架的氨基甲酸酯(甲基)丙烯酸酯、聚碳酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯、聚醚骨架的氨基甲酸酯(甲基)丙烯酸酯、聚酯骨架的氨基甲酸酯(甲基)丙烯酸酯、蓖麻油骨架的氨基甲酸酯(甲基)丙烯酸酯、异戊二烯系(甲基)丙烯酸酯、氢化异戊二烯系(甲基)丙烯酸酯、环氧(甲基)丙烯酸酯、含有(甲基)丙烯酰基的丙烯酸聚合物等。
<(D)成分>
作为用于本发明的(D)成分的光自由基聚合引发剂,只要是通过照射活性能量射线而发生自由基的化合物,则没有限定。另外,从能够同时实现固化物的隐蔽性以及光固化性树脂组合物的厚膜固化性的观点出发,优选为在365nm以上的波长区域具有吸收的光自由基聚合引发剂。另外,作为(D)成分,例如,可以列举出:苯乙酮系光自由基聚合引发剂、苯偶姻系光自由基聚合引发剂、二苯甲酮系光自由基聚合引发剂、噻吨酮系光自由基聚合引发剂、酰基氧化膦系光自由基聚合引发剂、二茂钛系光自由基聚合引发剂等,其中,从光固化性树脂组合物的厚膜固化性以及固化物的隐蔽性优良的观点出发,优选包含苯乙酮系光自由基聚合引发剂以及酰基氧化膦系光自由基聚合引发剂中的至少一种。另外,这些可以单独使用,也可以并用二种以上。
作为上述苯乙酮系光自由基聚合引发剂,例如,可以列举出:二乙氧基苯乙酮、2-羟基-2-甲基-1-苯基-丙烷-1-酮、苄基二甲基缩酮、4-(2-羟基乙氧基)苯基-(2-羟基-2-丙基)酮、1-羟基-环己基-苯基-酮、2-甲基-2-吗啉基(4-硫甲基苯基)丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-吗啉基苯基)丁酮、2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙酮低聚物等,但不限于此。作为上述苯乙酮系光自由基聚合引发剂的市售品,可以列举出:IRGACURE 184、DAROCUR 1173、IRGACURE 2959、IRGACURE 127(BASF公司制)、ESACURE KIP-150(Lamberti s.p.a.公司制)等。
作为上述酰基氧化膦系光自由基聚合引发剂,例如,可以列举出:双(2,4,6-三甲基苯甲酰基)-苯基-氧化膦、2,4,6-三甲基苯甲酰基-二苯基-氧化膦等,但不限于此。作为上述酰基氧化膦系光自由基聚合引发剂的市售品,可以列举出:LUCIRIN TPO、IRGACURE819、IRGACURE819DW(BASF公司制)等。
关于本发明的(D)成分的配合量,相对于(C)成分100质量份,优选为0.1~15质量份,更优选为1~10质量份。上述(D)成分为0.1质量份以上时,能够提高由活性能量射线引起的光固化性树脂组合物的厚膜固化性,为15质量份以下时,能够提高光固化性树脂组合物的保存稳定性。
<(E)成分>
作为本发明的(E)成分的叔胺化合物,通过与本发明的(A)~(D)成分组合,能够提供同时实现优良的贮藏稳定性以及厚膜固化性的光固化性树脂组合物。上述(E)成分从光固化性树脂组合物的贮藏稳定性的观点出发,优选为不包含伯或仲氨基、仅具有叔氨基的化合物。另外,通过上述(E)成分提高光固化性树脂组合物的厚膜固化性的理由还不明确,但推测是由于,通过(E)成分能够使利用酸的无色染料的发色延迟,在膜形成时可以使光透射至深部。另外,通过(E)成分提高光固化性树脂组合物的贮藏稳定性的理由还不明确,但可以认为,如果为伯或仲胺化合物,则在与(C)成分之间发生迈克尔加成反应,因此光固化性树脂组合物的贮藏稳定性变差。需要说明的是,如果为本发明的(E)成分,则与(C)成分不会发生迈克尔加成反应,因此光固化性树脂组合物的贮藏稳定性提高。但是,本发明的技术范围不限于上述推论。
作为上述(E)成分,没有特别限定,例如,可以列举出:N-苯基二乙醇胺、N-甲基二乙醇胺、对甲基苯基二乙醇胺、N-乙基二乙醇胺、N-丙基二乙醇胺、N-丁基二乙醇胺、三乙醇胺、三丁醇胺、三异丙醇胺、N-甲基二乙醇胺或N-甲基二甲醇胺等取代基中的至少一种为碳原子数1~8的直链状或支链状的羟烷基的叔胺化合物;三甲基胺、三乙基胺、三丁基胺、N,N-二甲基-对甲苯胺、N,N-二甲基-苯胺、N,N-(二甲基氨基)乙基-甲基丙烯酸酯、N,N-二甲基氨基苯乙酮、N,N-二甲基氨基二苯甲酮、N,N-二乙基氨基-二苯甲酮、N-甲基哌啶、N-乙基哌啶、N,N-二甲基苄基胺、N,N-二甲基环己基胺、丙烯酰吗啉、吗啉基乙基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二乙基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基丙基(甲基)丙烯酸酯等。这些可以使用1种,也可以混合使用二种以上。这些中,由于光固化性树脂组合物的贮藏稳定性优良,固化物的隐蔽性以及光固化性树脂组合物的厚膜固化性优良,(E)成分优选为:上述取代基中的至少一种为碳原子数1~8的直链状或支链状的羟烷基的叔胺化合物;选自丙烯酰吗啉、吗啉基乙基(甲基)丙烯酸酯、二甲基氨基乙基(甲基)丙烯酸酯、二乙基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯以及N,N-二甲基氨基丙基(甲基)丙烯酸酯中的至少一种。另外,除了上述观点之外,从能够减少后述的(E)成分相对于(C)成分的配合量的观点出发,(E)成分更优选包含取代基中的至少一种为碳原子数1~8的直链状或支链状的羟烷基的叔胺化合物至少一种。
关于本发明的(E)成分的配合量,相对于(C)成分100质量份,优选为0.01~200质量份,更优选为0.05~150质量份,特别优选为0.1~100质量份。(E)成分的配合量为0.01质量份以上时,能够提高由活性能量射线引起的光固化性树脂组合物的厚膜固化性,为200质量份以下时,能够提高固化物的隐蔽性。另外,作为(E)成分,包含取代基中的至少一种为碳原子数1~8的直链状或支链状的羟烷基的叔胺化合物至少一种的情况下,可以减少(E)成分相对于(C)成分的配合量,相对于(C)成分100质量份,为0.01~20质量份,优选为0.05~15质量份,更优选为0.1~10质量份。
另外,关于(E)成分以及(B)成分的配合量,从能够同时实现高隐蔽性和厚膜固化性的观点出发,相对于(C)成分100质量份,优选含有上述(E)成分0.01~100质量份、以及(B)成分0.01~10质量份。
针对本发明,在不损害本发明的目的的范围内,可以使用苯乙烯系共聚合物等各种弹性体、聚硫醇化合物、敏化剂、填充材料、保存稳定剂、抗氧化剂、光稳定剂、保存稳定剂、重金属钝化剂、密合赋予剂、增塑剂、消泡剂、颜料、防锈剂、匀化剂、分散剂、流变调节剂、阻燃剂、以及表面活性剂等添加剂。
针对本发明,为了提高光固化性,可以添加聚硫醇化合物。作为聚硫醇化合物,可以列举出:三羟甲基丙烷三(3-巯基丙酸酯)、季戊四醇四(3-巯基丙酸酯)、三羟甲基丙烷三(3-巯基丁酸酯)、三羟甲基乙烷三(3-巯基丁酸酯)、乙二醇双(3-巯基乙醇酸酯)、丁烷二醇双(3-巯基乙醇酸酯)、三羟甲基丙烷三(3-巯基乙醇酸酯)、季戊四醇四(3-巯基乙醇酸酯)、三-[(3-巯基丙酰氧基)-乙基]-异氰脲酸酯、季戊四醇四(3-巯基丙酸酯)、四乙二醇双(3-巯基丙酸酯)、二季戊四醇六(3-巯基丙酸酯)、季戊四醇四(3-巯基丁酸酯)、1,4-双(3-巯基丁酰氧基)丁烷、1,3,5-三(3-巯基丁氧乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮等。
针对本发明,为了提高光固化性,可以添加敏化剂。作为敏化剂,例如,可以列举出:蒽、芘、苝、呫吨酮、噻吨酮、曙红、酮香豆素、香豆素、异苯并呋喃等。
针对本发明,为了改良固化物的弹性模量、流动性等,可以添加不损害光固化性树脂组合物的厚膜固化性以及贮藏稳定性的程度的填充材料。具体而言,可以列举出有机质粉体、无机质粉体、金属质粉体等。
作为上述无机质粉体的填充材料,可以列举出:玻璃、煅制二氧化硅、氧化铝、云母、陶瓷、硅酮橡胶粉体、碳酸钙、氮化铝、碳粉、高岭土、干燥粘土矿物、干燥硅藻土等。关于无机质粉体的配合量,相对于(A)成分100质量份,优选为0.1~100质量份。为0.1质量份以上时,得到固化物的弹性模量、流动性等的改良效果,为100质量份以下时,光固化性树脂组合物的流动性优良,作业性提高。
上述煅制二氧化硅可以为了提高光固化性树脂组合物的粘度调节或固化物的机械强度而配合。优选使用用二甲基硅烷、三甲基硅烷、烷基硅烷、甲基丙烯酰氧基硅烷、有机氯硅烷、聚二甲基硅氧烷、六甲基二甲硅基胺等进行表面处理后的煅制二氧化硅。作为煅制二氧化硅的市售品,例如,可以列举出:Aerosil(注册商标)R972、R972V、R972CF、R974、R976、R976S、R9200、RX50、NAX50,NX90、RX200、RX300、R812、R812S、R8200、RY50、NY50、RY200S、RY200、RY300、R104、R106、R202、R805、R816、T805、R711、RM50、R7200(日本Aerosil株式会社制)等。
作为上述有机质粉体的填充材料,例如,可以列举出:聚乙烯、聚丙烯、尼龙、交联丙烯酸、交联聚苯乙烯、聚酯、聚乙烯醇、聚乙烯醇缩丁醛、聚碳酸酯等。关于有机质粉体的配合量,相对于(A)成分100质量份,优选为0.1~100质量份。为0.1质量份以上时,得到固化物的弹性模量、流动性等的改良效果,为100质量份以下时,光固化性树脂组合物的流动性优良,作业性提高。
本发明中,可以添加保存稳定剂。作为上述保存稳定剂,可以添加苯醌、对苯二酚、对苯二酚单甲基醚等自由基吸收剂、乙二胺四乙酸或其2-钠盐、草酸、乙酰丙酮、邻氨基苯酚等的金属螯合剂等。
针对本发明,可以添加抗氧化剂。作为上述抗氧化剂,例如,可以列举出:β-萘醌、2-甲氧基-1,4-萘醌、甲基对苯二酚、对苯二酚、对苯二酚单甲基醚、单-叔丁基对苯二酚、2,5-二-叔丁基对苯二酚、对苯醌、2,5-二苯基-对苯醌、2,5-二-叔丁基-对苯醌等醌系化合物;吩噻嗪、2,2-亚甲基-双(4-甲基-6-叔丁基苯酚)、邻苯二酚、叔丁基邻苯二酚、2-丁基-4-羟基茴香醚、2,6-二-叔丁基-对甲酚、2-叔丁基-6-(3-叔丁基-2-羟基-5-甲基苄基)-4-甲基苯基丙烯酸酯、2-[1-(2-羟基-3,5-二-叔戊基苯基)乙基]-4,6-二-叔戊基苯基丙烯酸酯、4,4'-亚丁基双(6-叔丁基-3-甲基苯酚)、4,4'-硫代双(6-叔丁基-3-甲基苯酚)、3,9-双[2-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基]-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5,5]十一烷、季戊四醇四[3-(3,5-二-叔丁基-4-羟基苯基)丙酸酯]、硫代二亚乙基双[3-(3,5-二-叔丁基-4-羟基苯基)丙酸酯]、十八烷基-3-(3,5-二-叔丁基-4-羟基苯基)丙酸酯、N,N'-己烷-1,6-二基双[3-(3,5-二-叔丁基-4-羟基苯基)丙酰胺]、苯丙酸、3,5-双(1,1-二甲基乙基)-4-羟基、C7~C9侧链烷酯、2,4-二甲基-6-(1-甲基十五烷基)苯酚、二乙基[[3,5-双(1,1-二甲基乙基)-4-羟基苯基]甲基]膦酸酯、3,3',3”,5,5',5”-六-叔丁基-a,a',a”-(均三甲苯-2,4,6-甲苯基)三-对甲酚、二乙基双[[3,5-双(1,1-二甲基乙基)-4-羟基苯基]甲基]膦酸钙、4,6-双(辛基硫甲基)-邻甲酚、亚乙基双(氧亚乙基)双[3-(5-叔丁基-4-羟基-间甲苯基)丙酸酯]、六亚甲基双[3-(3,5-二-叔丁基-4-羟基苯基)丙酸酯、1,3,5-三(3,5-二-叔丁基-4-羟基苄基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、1,3,5-三[(4-叔丁基-3-羟基-2,6-二甲苯基)甲基]-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、N-苯基苯胺与2,4,6-三甲基戊烯的反应产物、2,6-二-叔丁基-4-(4,6-双(辛基硫代)-1,3,5-三嗪-2-基氨基)苯酚、苦味酸等酚系化合物;三(2,4-二-叔丁基苯基)亚磷酸酯、三[2-[[2,4,8,10-四-叔丁基二苯并[d,f][1,3,2]二氧杂膦-6-基]氧基]乙基]胺、双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯、双[2,4-双(1,1-二甲基乙基)-6-甲基苯基]乙基酯亚磷酸、四(2,4-二-叔丁基苯基)[1,1-双苯基]-4,4'-二基双亚磷酸酯、6-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙氧基]-2,4,8,10-四-叔丁基二苯并[d,f][1,3,2]二氧杂膦等磷系化合物;3,3'-硫代二丙酸二月桂基酯、3,3'-硫代二丙酸二肉豆蔻基酯、3,3'-硫代二丙酸二硬脂基酯、季戊四醇四(3-月桂基硫代丙酸酯)、内酯系化合物;维生素E系化合物等。其中,优选为酚系化合物。
针对本发明,可以添加密合赋予剂。作为上述密合赋予剂,可以列举出:γ-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三氯硅烷、乙烯基三乙氧基硅烷、乙烯基-三(β-甲氧基乙氧基)硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷、γ-脲基丙基三乙氧基硅烷等。关于密合赋予剂的配合量,相对于(C)成分100质量份,优选为0.05~30质量份,更优选为0.2~10质量份。
本发明的光固化性树脂组合物可以通过公知的方法制造。可以通过例如配合规定量的(A)~(E)成分,使用混合机等混合装置,在10~70℃的温度下混合0.1~5小时来制造。
通过照射紫外线、可见光等光使本发明的光固化性树脂组合物固化时的光源,没有特别限定,例如,可以列举出:低压水银灯、中压水银灯、高压水银灯、超高压水银灯、黑光灯、微波激发水银灯、金属卤化物灯、钠灯、卤素灯、氙灯、LED、荧光灯、太阳光、电子射线照射装置等。关于光照射的照射量,从固化物的特性的观点出发,优选为10kJ/m2以上,更优选为20kJ/m2以上。关于上述光照射的照射量的上限,从生产率的观点出发,优选为1000kJ/m2以下。
本发明的光固化性树脂组合物,通过作为(A)成分的无色染料与酸接触而发色,将上述光固化性树脂组合物固化而得到的固化物可以发色成黑色、蓝色、绿色、红色等。上述固化物从隐蔽性优良的观点出发,优选为黑色。
作为适用于本发明的光固化性树脂组合物的用途,可以列举出:铸造用树脂、密封剂、密封材料、灌封剂、胶粘剂、被覆材料、内衬材料、油墨等。其中,作为上述用途,本发明的光固化性树脂组合物由于贮藏稳定性优良,具有固化物的高隐蔽性和优良的厚膜固化性,因此优选为铸造用树脂、密封剂、灌封剂、胶粘剂或被覆材料用途。需要说明的是,在这样的用途中使用时,本发明的光固化性树脂组合物优选在25℃下为液状。
作为本发明的光固化性树脂组合物的特别优选的用途,可以列举出:面向挠性电路板的被覆材料、铸造用树脂、透镜的黑条、图像显示装置、光学构件、CMOS传感器、框体与透镜等的组装用胶粘剂等。
实施例
以下,列举实施例,进一步对本发明详细地进行说明,但本发明不受这些实施例的限定。
<光固化性树脂组合物的制备>
以表1所示的质量份采集各成分,在常温(25℃)下用行星式混合机混合60分钟,制备光固化性树脂组合物。需要说明的是,详细的制备量依据表1,数值全部用质量份表示。
<(A)成分>
a1:3-二丁基氨基-6-甲基-7-苯胺基荧烷(ODB-2、山本化成株式会社制)
a2:3-二乙基氨基-6-甲基-7-苯胺基荧烷(ODB、山本化成株式会社制)
<(A)成分的比较成分>
a'1:碳黑(SRB黑T-04、御国色素株式会社制)
<(B)成分>
b1:三芳基锍-六氟磷酸盐(CPI-100P、SANAPRO株式会社制)
<(C)成分>
c1:氨基甲酸酯(甲基)丙烯酸酯(UV-3000B、日本合成化学工业株式会社制)
c2:异氰脲酸EO改性二以及三丙烯酸酯(M-313、东亚合成社制)
c3:二羟甲基-三环癸烷二丙烯酸酯(DCPA、共荣社化学株式会社制)
c4:丙烯酸异冰片酯(Light Acrylate IBX-A、共荣社化学株式会社制)
<(D)成分>
d1:2-羟基-2-甲基-1-苯基-丙烷-1-酮(DAROCUR1173、BASF公司制)
d2:2,4,6-三甲基苯甲酰基-二苯基-氧化膦(LUCIRIN TPO、BASF公司制)
<(E)成分>
e1:丙烯酰基吗啉(ACMO、KJ chemicals株式会社制)
e2:三异丙醇胺(东京化成工业株式会社制)
e3:三乙醇胺(东京化成工业株式会社制)
e4:N-苯基二乙醇胺(东京化成工业株式会社制)
<(E)成分的比较成分>
e'1:N-羟甲基丙烯酰胺
e'2:甲基丙烯酰胺
e'3:1,3-双氨基甲基环己烷(1,3-BAC、三菱气体化学株式会社制)
e'4:3,3'-二乙基-4,4'-二氨基二苯基甲烷(KAYAHARD A-A、日本化药株式会社制)
e'5:聚氧丙二胺(ジェファーミンD-230)
e'6:间二甲苯二胺(MXDA、三菱瓦斯化学株式会社制)。
实施例以及比较例中使用的试验方法如下。
<固化物的外观确认>
将光固化性树脂组合物以厚度达到0.5mm的方式制作表面平滑的试验片,使用LED照射机(波长365nm),在100mW/cm2×120秒的条件下进行紫外线照射,得到固化物。目视观察其固化物的外观,将其结果总结示于表1。
<隐蔽性的评价>
将光固化性树脂组合物以厚度达到0.5mm的方式制作表面平滑的试验片,使用LED照射机(波长365nm),在100mW/cm2×120秒的条件下进行紫外线照射,得到固化物。在标有黑点的纸上,放置所得到的固化物,目视观察黑点,基于下述基准进行评价。将其结果总结示于表1。
[评价基准]
○:黑点的轮廓不清晰,隐蔽性能够观察的情况
×:黑点的轮廓清晰时,被观察的情况。
<厚膜固化性的评价>
将光固化性树脂组合物装入深度5mm的金属筒中,使用LED照射机(波长365nm),在100mW/cm2×120秒的条件下进行紫外线照射,使其光固化,得到固化物。另外,通过用溶剂除去未固化部分,用卡尺测定固化部分,计算出厚膜固化性。将其结果总结示于表1。
需要说明的是,为了适用于铸造用树脂,优选为1mm以上的厚膜固化性。
<贮藏稳定性的评价>
将固化性树脂组合物5g在25℃室内装入遮光容器中,密闭保存1个月,然后,基于下述基准,目视进行评价。将其结果总结示于表1。
[评价基准]
○:液状的状态,贮藏稳定性良好
×:观察到凝胶化。
[表1]
根据表1可知,实施例1~7为含有(E)成分的叔胺化合物的光固化性树脂组合物,具有优良的膜厚固化性,并且固化物具有高隐蔽性,另外具有优良的贮藏稳定性。
另外可知,比较例1为不含有本发明的(E)成分的光固化性树脂组合物,与实施例1~7比较,厚膜固化性变差。另外,比较例2以及3为含有不是本发明的(E)成分的e'1、e'2成分的光固化性树脂组合物,但无法在本发明的(C)成分中溶解。另外,比较例4~7为含有不是本发明的(E)成分的伯或仲胺化合物的e'3~6中的任一个的光固化性树脂组合物,但在制造组合物时观察到凝胶化,因此具有贮藏稳定性变差的结果。另外,比较例8为含有不是本发明的(A)成分的碳黑的光固化性树脂组合物,由于碳黑吸收紫外线,因此具有光固化性树脂组合物的厚膜固化性显著差的结果。
<固化物的透过率测定>
将实施例1~7的各固化性树脂组合物以厚度达到150μm的方式制作表面平滑的试验片,在100mW/cm2×120秒的条件下进行紫外线照射,得到固化物。用分光光度计UV-2450(岛津制作所制)测定该固化物的透过率(表1中没有记载)。实施例1~7的各固化性树脂组合物的固化物的评价结果全部是550nm的波长的透过率为3%以下,观察到优良的隐蔽性。
产业上的利用可能性
本发明的光固化性树脂组合物的贮藏稳定性优良,具有高隐蔽性和厚膜固化性,因此适合用于各种胶粘用途。具体而言,作为被覆材料、铸造用树脂、密封剂、密封材料、灌封剂、胶粘剂、被覆材料、内衬材料、胶粘剂、油墨等极其有效,能够适用于广泛的领域。
需要说明的是,本发明的应用不限于上述的实施方式,可以在不脱离本发明的主旨的范围内适当变更。
本申请基于在2014年9月29日申请的日本专利申请号2014-197803号,参照其公开内容,作为整体被引入。
Claims (8)
1.一种光固化性树脂组合物,其含有(A)~(E)成分,
(A)成分:无色染料、
(B)成分:光致产酸剂、
(C)成分:自由基聚合性化合物,其中,不包括具有叔胺骨架的(甲基)丙烯酸酯、
(D)成分:光自由基聚合引发剂、
(E)成分:叔胺化合物,
相对于所述(C)成分100质量份,含有所述(E)成分0.01~200质量份;
所述(A)成分为选自3-二丁基氨基-6-甲基-7-苯胺基荧烷、3-二丙基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-苯胺基荧烷、3-二甲基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-二甲代苯胺基荧烷和3-(4-二乙基氨基-2-乙氧基苯基)-3-(1-乙基-2-甲基吲哚-3-基)-4-氮杂苯酞中的至少一种;
所述(E)成分为选自N-苯基二乙醇胺、N-甲基二乙醇胺、对甲基苯基二乙醇胺、N-乙基二乙醇胺、N-丙基二乙醇胺、N-丁基二乙醇胺、三乙醇胺、三丁醇胺、三异丙醇胺、N-甲基-二乙醇胺、N-甲基-二甲醇胺、三甲基胺、三乙基胺、三丁基胺、N,N-二甲基-对甲苯胺、N,N-二甲基-苯胺、N,N-(二甲基氨基)乙基-甲基丙烯酸酯、N,N-二甲基氨基苯乙酮、N,N-二甲基氨基二苯甲酮、N,N-二乙基氨基二苯甲酮、N-甲基哌啶、N-乙基哌啶、N,N-二甲基苄胺、N,N-二甲基环己胺、丙烯酰吗啉、吗啉基乙基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二乙基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基丙基(甲基)丙烯酸酯中的至少一种。
2.根据权利要求1所述的光固化性树脂组合物,其中,
相对于所述(C)成分100质量份,含有所述(E)成分0.01~100质量份、以及(B)成分0.01~10质量份。
3.根据权利要求1所述的光固化性树脂组合物,其中,
所述(C)成分包含低聚物和单体。
4.根据权利要求1所述的光固化性树脂组合物,其中,
所述(D)成分包含苯乙酮系光自由基聚合引发剂以及酰基氧化膦系光自由基聚合引发剂中的至少一种。
5.根据权利要求1所述的光固化性树脂组合物,其中,
所述(B)成分为鎓盐系光致产酸剂。
6.根据权利要求1所述的光固化性树脂组合物,其中,
所述(B)成分为芳基锍盐。
7.根据权利要求1所述的光固化性树脂组合物,其特征在于,
固化物为黑色。
8.根据权利要求1~7中任一项所述的光固化性树脂组合物,
其为铸造用树脂、密封剂、灌封剂、胶粘剂或被覆材料用光固化性树脂组合物。
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