CN106125509A - 用于加成法制造的可led固化的液体树脂组合物 - Google Patents
用于加成法制造的可led固化的液体树脂组合物 Download PDFInfo
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- CN106125509A CN106125509A CN201610479298.8A CN201610479298A CN106125509A CN 106125509 A CN106125509 A CN 106125509A CN 201610479298 A CN201610479298 A CN 201610479298A CN 106125509 A CN106125509 A CN 106125509A
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- Prior art keywords
- phenyl
- sulfonium
- resin composition
- light
- photocurable resin
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 106
- 239000011342 resin composition Substances 0.000 title claims abstract description 82
- 230000008569 process Effects 0.000 title claims abstract description 80
- 239000007788 liquid Substances 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title abstract description 50
- 238000007711 solidification Methods 0.000 title abstract description 27
- 230000008023 solidification Effects 0.000 title abstract description 27
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 31
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 27
- 239000007787 solid Substances 0.000 claims abstract description 18
- 230000000977 initiatory effect Effects 0.000 claims abstract description 17
- -1 4-(4-benzoylphenylsulfanyl) phenyl Chemical group 0.000 claims description 212
- 239000000203 mixture Substances 0.000 claims description 74
- 239000002585 base Substances 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 239000003999 initiator Substances 0.000 claims description 48
- 239000011347 resin Substances 0.000 claims description 45
- 229920005989 resin Polymers 0.000 claims description 45
- 150000001768 cations Chemical class 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- 239000011593 sulfur Substances 0.000 claims description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 35
- 150000003254 radicals Chemical class 0.000 claims description 29
- 230000005855 radiation Effects 0.000 claims description 27
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 26
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 150000003568 thioethers Chemical class 0.000 claims description 14
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 230000035515 penetration Effects 0.000 claims description 8
- RMVRSNDYEFQCLF-UHFFFAOYSA-O phenylsulfanium Chemical compound [SH2+]C1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-O 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
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- 125000003118 aryl group Chemical group 0.000 claims description 6
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- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 4
- ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical compound C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012953 triphenylsulfonium Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
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- 125000001544 thienyl group Chemical group 0.000 claims description 3
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 claims description 2
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 238000012663 cationic photopolymerization Methods 0.000 claims description 2
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- 239000003063 flame retardant Substances 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
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- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- IIISVPHVLPCACA-UHFFFAOYSA-N NCC1=CC=C(C=C1)C1=C(C=CC(=C1)C(C)C)I Chemical compound NCC1=CC=C(C=C1)C1=C(C=CC(=C1)C(C)C)I IIISVPHVLPCACA-UHFFFAOYSA-N 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 238000012690 ionic polymerization Methods 0.000 claims 1
- QQBDOJUNCZSRGA-UHFFFAOYSA-N phenyl-(4-phenylsulfanylphenyl)methanone Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 QQBDOJUNCZSRGA-UHFFFAOYSA-N 0.000 claims 1
- 238000000016 photochemical curing Methods 0.000 abstract description 4
- 238000007792 addition Methods 0.000 description 62
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- 239000003504 photosensitizing agent Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
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- 239000012965 benzophenone Substances 0.000 description 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
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- 150000001450 anions Chemical class 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
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- 239000004593 Epoxy Substances 0.000 description 9
- 150000002118 epoxides Chemical class 0.000 description 9
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
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- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 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 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
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- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 6
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- 229910019142 PO4 Inorganic materials 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 6
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 5
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Abstract
Description
实施例编号 | CPI/RPI | CPC/RPC |
1 | 1.33 | 1.13 |
2 | 0.18 | 3.19 |
3 | 0.25 | 3.19 |
4 | 0.43 | 3.19 |
5 | 0.67 | 3.19 |
6 | 0.67 | 1.37 |
7 | 0.67 | 1.30 |
8 | 0.67 | 1.23 |
9 | 0.67 | 1.33 |
10 | 0.67 | 1.33 |
11 | 0.67 | 1.47 |
12 | 0.67 | 1.55 |
13 | 0.67 | 1.47 |
14 | 0.67 | 1.47 |
15 | 0.25 | 1.48 |
16 | 0.25 | 1.48 |
17 | 0.25 | 1.48 |
18 | 0.25 | 1.48 |
19 | 0.25 | 2.23 |
20 | 0.25 | 2.27 |
21 | 0.25 | 2.23 |
22 | 0.25 | 0.94 |
23 | 0.25 | N/A |
24 | 0.25 | N/A |
25 | 0.25 | N/A |
26 | 0.25 | N/A |
27 | 0.25 | N/A |
28 | 0.25 | 0.54 |
29 | 0.25 | 0.54 |
30 | 0.25 | 0.54 |
实施例编号 | CPI/RPI | CPC/RPC |
31 | 0.82 | 3.56 |
32 | 0.76 | 1.10 |
33 | 0.76 | 1.10 |
34 | 0.82 | 3.56 |
35 | 1.22 | 3.56 |
36 | 1.26 | 1.10 |
37 | 0.50 | 1.87 |
38 | 0.50 | 1.87 |
39 | 0.50 | 1.87 |
40 | 0.50 | 1.87 |
41 | 0.50 | 1.87 |
42 | 0.50 | 1.87 |
43 | 0.50 | 1.87 |
44 | 0.50 | 1.87 |
45 | 0.71 | 6.50 |
46 | 0.71 | 6.50 |
47 | 0.88 | 6.53 |
48 | 4.09 | 6.53 |
49 | 1.02 | 6.53 |
50 | 0.70 | 6.53 |
51 | 0.35 | 6.53 |
52 | 1.29 | 6.53 |
53 | 1.29 | 6.53 |
54 | 1.29 | 6.53 |
55 | 1.29 | 6.53 |
56 | 0.40 | 6.56 |
Claims (11)
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