CN106125509B - 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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- CN106125509B CN106125509B CN201610479298.8A CN201610479298A CN106125509B CN 106125509 B CN106125509 B CN 106125509B CN 201610479298 A CN201610479298 A CN 201610479298A CN 106125509 B CN106125509 B CN 106125509B
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- photocurable resin
- additive fabrication
- phenyl
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- 239000007788 liquid Substances 0.000 title claims abstract description 23
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 26
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 17
- 230000000977 initiatory effect Effects 0.000 claims abstract description 14
- -1 aromatic sulfonium salt Chemical class 0.000 claims description 193
- 239000000203 mixture Substances 0.000 claims description 50
- 239000012952 cationic photoinitiator Substances 0.000 claims description 45
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- 150000003254 radicals Chemical class 0.000 claims description 27
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 22
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 17
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 13
- 239000012949 free radical photoinitiator Substances 0.000 claims description 12
- 230000035515 penetration Effects 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 7
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- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 claims description 6
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- 239000002245 particle Substances 0.000 claims description 5
- QKAIFCSOWIMRJG-UHFFFAOYSA-N (4-methylphenyl)-(4-propan-2-ylphenyl)iodanium Chemical compound C1=CC(C(C)C)=CC=C1[I+]C1=CC=C(C)C=C1 QKAIFCSOWIMRJG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
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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 3
- 239000012953 triphenylsulfonium Substances 0.000 claims description 3
- 239000004609 Impact Modifier Substances 0.000 claims description 2
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- 239000006096 absorbing agent 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
- AENNXXRRACDJAY-UHFFFAOYSA-N bis(2-dodecylphenyl)iodanium Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC AENNXXRRACDJAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011258 core-shell material Substances 0.000 claims description 2
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 claims description 2
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- QNFNZVLBTGUIQY-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenoxy)borinic acid Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F QNFNZVLBTGUIQY-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 36
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- 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 10
- 239000012965 benzophenone Substances 0.000 description 10
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- 125000002091 cationic group Chemical group 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 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 5
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 5
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
- 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 5
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 5
- 150000007964 xanthones Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
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- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 4
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- DIYFBIOUBFTQJU-UHFFFAOYSA-N 1-phenyl-2-sulfanylethanone Chemical class SCC(=O)C1=CC=CC=C1 DIYFBIOUBFTQJU-UHFFFAOYSA-N 0.000 description 3
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 3
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- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl 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])[H] 0.000 description 1
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Classifications
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- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
- B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
- B29C35/08—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
- B29C35/0805—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
- B29C2035/0838—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using laser
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31515—As intermediate layer
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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)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US28762009P | 2009-12-17 | 2009-12-17 | |
US61/287,620 | 2009-12-17 | ||
CN201080057944.2A CN102934026B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的可led固化的液体树脂组合物 |
Related Parent Applications (1)
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CN201080057944.2A Division CN102934026B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的可led固化的液体树脂组合物 |
Publications (2)
Publication Number | Publication Date |
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CN106125509A CN106125509A (zh) | 2016-11-16 |
CN106125509B true CN106125509B (zh) | 2019-12-17 |
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Application Number | Title | Priority Date | Filing Date |
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CN201080057939.1A Active CN102666073B (zh) | 2009-12-17 | 2010-12-16 | 基于基材的加成法制造工艺 |
CN201610479298.8A Active CN106125509B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的可led固化的液体树脂组合物 |
CN201080057944.2A Active CN102934026B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的可led固化的液体树脂组合物 |
CN201080057942.3A Active CN102858738B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的包含三芳基锍硼酸盐阳离子光引发剂的液体可辐射固化树脂 |
Family Applications Before (1)
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CN201080057939.1A Active CN102666073B (zh) | 2009-12-17 | 2010-12-16 | 基于基材的加成法制造工艺 |
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Application Number | Title | Priority Date | Filing Date |
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CN201080057944.2A Active CN102934026B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的可led固化的液体树脂组合物 |
CN201080057942.3A Active CN102858738B (zh) | 2009-12-17 | 2010-12-16 | 用于加成法制造的包含三芳基锍硼酸盐阳离子光引发剂的液体可辐射固化树脂 |
Country Status (7)
Country | Link |
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US (3) | US9034236B2 (zh) |
EP (3) | EP2512779B1 (zh) |
JP (2) | JP5849350B2 (zh) |
KR (4) | KR101821426B1 (zh) |
CN (4) | CN102666073B (zh) |
BR (2) | BR112012014900B1 (zh) |
WO (3) | WO2011084578A1 (zh) |
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