JP2018527442A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018527442A5 JP2018527442A5 JP2018511267A JP2018511267A JP2018527442A5 JP 2018527442 A5 JP2018527442 A5 JP 2018527442A5 JP 2018511267 A JP2018511267 A JP 2018511267A JP 2018511267 A JP2018511267 A JP 2018511267A JP 2018527442 A5 JP2018527442 A5 JP 2018527442A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- cyanatophenyl
- phenyl
- weight percent
- optionally
- 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
- 239000004643 cyanate ester Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 42
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 230000000269 nucleophilic effect Effects 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- -1 Cyanatophenyl Chemical group 0.000 claims description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910017052 cobalt Inorganic materials 0.000 claims description 12
- 239000010941 cobalt Substances 0.000 claims description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 12
- 239000003426 co-catalyst Substances 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- YKONYNBAMHVIMF-UHFFFAOYSA-N [2,6-dichloro-4-[2-(3,5-dichloro-4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C(Cl)=C(OC#N)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(OC#N)C(Cl)=C1 YKONYNBAMHVIMF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 239000011133 lead Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 8
- 239000011135 tin Substances 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 8
- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 229930185605 Bisphenol Natural products 0.000 claims description 6
- 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 claims description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- CFTSORNHIUMCGF-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 CFTSORNHIUMCGF-UHFFFAOYSA-N 0.000 claims description 4
- CNRPKWSJHKEVPD-UHFFFAOYSA-N (2,2,2-trifluoro-1-phenylethyl)benzene Chemical group C=1C=CC=CC=1C(C(F)(F)F)C1=CC=CC=C1 CNRPKWSJHKEVPD-UHFFFAOYSA-N 0.000 claims description 4
- PYGFCFSLFFALAX-UHFFFAOYSA-N (2,5-ditert-butyl-4-cyanatophenyl) cyanate Chemical compound CC(C)(C)C1=CC(OC#N)=C(C(C)(C)C)C=C1OC#N PYGFCFSLFFALAX-UHFFFAOYSA-N 0.000 claims description 4
- XWXIRFDZSUBXKO-UHFFFAOYSA-N (2-chloro-4-methylphenyl) cyanate Chemical compound ClC=1C=C(C=CC=1OC#N)C XWXIRFDZSUBXKO-UHFFFAOYSA-N 0.000 claims description 4
- IALZLVVOMYFDGE-UHFFFAOYSA-N (2-chloro-5-cyanatophenyl) cyanate Chemical compound ClC1=CC=C(OC#N)C=C1OC#N IALZLVVOMYFDGE-UHFFFAOYSA-N 0.000 claims description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 4
- NGGIZAWDYJYQBS-UHFFFAOYSA-N (2-tert-butyl-4-cyanatophenyl) cyanate Chemical compound CC(C)(C)C1=CC(OC#N)=CC=C1OC#N NGGIZAWDYJYQBS-UHFFFAOYSA-N 0.000 claims description 4
- UFKLQICEQCIWNE-UHFFFAOYSA-N (3,5-dicyanatophenyl) cyanate Chemical compound N#COC1=CC(OC#N)=CC(OC#N)=C1 UFKLQICEQCIWNE-UHFFFAOYSA-N 0.000 claims description 4
- YDCUTCGACVVRIQ-UHFFFAOYSA-N (3,6-dicyanatonaphthalen-1-yl) cyanate Chemical compound N#COC1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 YDCUTCGACVVRIQ-UHFFFAOYSA-N 0.000 claims description 4
- XSQMOWKODCDFPI-UHFFFAOYSA-N (3-cyanato-2,4-dimethylphenyl) cyanate Chemical compound CC1=CC=C(OC#N)C(C)=C1OC#N XSQMOWKODCDFPI-UHFFFAOYSA-N 0.000 claims description 4
- NZTBWEVKIDDAOM-UHFFFAOYSA-N (4-cyanato-2,3,5,6-tetramethylphenyl) cyanate Chemical compound CC1=C(C)C(OC#N)=C(C)C(C)=C1OC#N NZTBWEVKIDDAOM-UHFFFAOYSA-N 0.000 claims description 4
- GUGZCSAPOLLKNG-UHFFFAOYSA-N (4-cyanatophenyl) cyanate Chemical compound N#COC1=CC=C(OC#N)C=C1 GUGZCSAPOLLKNG-UHFFFAOYSA-N 0.000 claims description 4
- SGACLTVKXIFYLM-UHFFFAOYSA-N (4-phenylphenyl) cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=CC=C1 SGACLTVKXIFYLM-UHFFFAOYSA-N 0.000 claims description 4
- OFIWROJVVHYHLQ-UHFFFAOYSA-N (7-cyanatonaphthalen-2-yl) cyanate Chemical compound C1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 OFIWROJVVHYHLQ-UHFFFAOYSA-N 0.000 claims description 4
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 claims description 4
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical group C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
- CVIAERHUEXHJNW-UHFFFAOYSA-N 2,6-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(CCCCCCCCC)=C1O CVIAERHUEXHJNW-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 claims description 4
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 claims description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 4
- SIQHSJOKAUDDLN-UHFFFAOYSA-N 2-methyl-1-propylimidazole Chemical compound CCCN1C=CN=C1C SIQHSJOKAUDDLN-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 4
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 claims description 4
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 claims description 4
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 claims description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 4
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 claims description 4
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 claims description 4
- NGCFVIRRWORSML-UHFFFAOYSA-N 3-phenylbutan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)C(C)C1=CC=CC=C1 NGCFVIRRWORSML-UHFFFAOYSA-N 0.000 claims description 4
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 4
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 claims description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- MTFQJVVREUTRSO-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=CC=CC=C1)=O.C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)P(C1=CC=CC=C1)=O.C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1 MTFQJVVREUTRSO-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- WXVMBZDFEQHMFC-UHFFFAOYSA-N [2-chloro-4-[(3-chloro-4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound C1=C(OC#N)C(Cl)=CC(CC=2C=C(Cl)C(OC#N)=CC=2)=C1 WXVMBZDFEQHMFC-UHFFFAOYSA-N 0.000 claims description 4
- SUXGZGQKIFLKOR-UHFFFAOYSA-N [4-(2-phenylpropan-2-yl)phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=CC=C1 SUXGZGQKIFLKOR-UHFFFAOYSA-N 0.000 claims description 4
- SPPHTMLVUBCBKQ-UHFFFAOYSA-N [4-(4-cyanatobenzoyl)phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(=O)C1=CC=C(OC#N)C=C1 SPPHTMLVUBCBKQ-UHFFFAOYSA-N 0.000 claims description 4
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 claims description 4
- HEJGXMCFSSDPOA-UHFFFAOYSA-N [4-(4-cyanatophenyl)phenyl] cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=C(OC#N)C=C1 HEJGXMCFSSDPOA-UHFFFAOYSA-N 0.000 claims description 4
- CNUHQZDDTLOZRY-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfanylphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1SC1=CC=C(OC#N)C=C1 CNUHQZDDTLOZRY-UHFFFAOYSA-N 0.000 claims description 4
- BUPOATPDNYBPMR-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfonylphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1S(=O)(=O)C1=CC=C(OC#N)C=C1 BUPOATPDNYBPMR-UHFFFAOYSA-N 0.000 claims description 4
- AWWJTNMLTCVUBS-UHFFFAOYSA-N [4-[1,1-bis(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C=1C=CC(OC#N)=CC=1)(C)C1=CC=C(OC#N)C=C1 AWWJTNMLTCVUBS-UHFFFAOYSA-N 0.000 claims description 4
- PPZSVSGWDQKBIW-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphanyloxyphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OP(OC=1C=CC(OC#N)=CC=1)OC1=CC=C(OC#N)C=C1 PPZSVSGWDQKBIW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003926 acrylamides Chemical class 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 239000004305 biphenyl Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000006229 carbon black Substances 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 4
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 4
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical group C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 claims description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical group CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 239000011342 resin composition Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- HQWHIDZANPSZDF-UHFFFAOYSA-N 2-(2-ethyl-5-methyl-1H-imidazol-4-yl)propanenitrile 2-(2-undecyl-1H-imidazol-5-yl)propanenitrile Chemical compound CCc1nc(C(C)C#N)c(C)[nH]1.CCCCCCCCCCCc1ncc([nH]1)C(C)C#N HQWHIDZANPSZDF-UHFFFAOYSA-N 0.000 claims 2
- NFJVRDFPAUVTIA-UHFFFAOYSA-N 4-[2-(4-cyano-2-phenoxyphenoxy)phenoxy]-3-phenoxybenzonitrile Chemical compound C=1C=CC=CC=1OC1=CC(C#N)=CC=C1OC1=CC=CC=C1OC1=CC=C(C#N)C=C1OC1=CC=CC=C1 NFJVRDFPAUVTIA-UHFFFAOYSA-N 0.000 claims 2
- ZXNSTHWSPVMAEQ-UHFFFAOYSA-N O(C#N)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)OC#N.O(C#N)C1=CC=C(C=C1)CC1=CC=C(C=C1)OC#N Chemical compound O(C#N)C1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)OC#N.O(C#N)C1=CC=C(C=C1)CC1=CC=C(C=C1)OC#N ZXNSTHWSPVMAEQ-UHFFFAOYSA-N 0.000 claims 2
- SIZDMAYTWUINIG-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)C1=CC=C(OC#N)C=C1 SIZDMAYTWUINIG-UHFFFAOYSA-N 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 150000003923 2,5-pyrrolediones Chemical group 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- JDIPZHAYUYYGSN-UHFFFAOYSA-N (4-propylphenyl) cyanate Chemical compound CCCC1=CC=C(OC#N)C=C1 JDIPZHAYUYYGSN-UHFFFAOYSA-N 0.000 description 2
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 2
- ZYQLLWLCRXLFKB-UHFFFAOYSA-N 3-(2-undecyl-1h-imidazol-5-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC(CCC#N)=CN1 ZYQLLWLCRXLFKB-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- AUYQDAWLRQFANO-UHFFFAOYSA-N [4-[(4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1CC1=CC=C(OC#N)C=C1 AUYQDAWLRQFANO-UHFFFAOYSA-N 0.000 description 2
- UHCNCKOCZQCYRV-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1CCC1=CC=C(OC#N)C=C1 UHCNCKOCZQCYRV-UHFFFAOYSA-N 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562214601P | 2015-09-04 | 2015-09-04 | |
| US62/214,601 | 2015-09-04 | ||
| US201562270635P | 2015-12-22 | 2015-12-22 | |
| US62/270,635 | 2015-12-22 | ||
| PCT/US2016/050035 WO2017040883A1 (en) | 2015-09-04 | 2016-09-02 | Cyanate ester dual cure resins for additive manufacturing |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018527442A JP2018527442A (ja) | 2018-09-20 |
| JP2018527442A5 true JP2018527442A5 (cg-RX-API-DMAC7.html) | 2019-10-10 |
| JP7069006B2 JP7069006B2 (ja) | 2022-05-17 |
Family
ID=56940401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018511267A Active JP7069006B2 (ja) | 2015-09-04 | 2016-09-02 | 積層造形用シアネートエステル二重硬化樹脂 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US10471655B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3344676B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP7069006B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN108350145B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2017040883A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018165090A1 (en) | 2017-03-09 | 2018-09-13 | Carbon, Inc. | Tough, high temperature polymers produced by stereolithography |
| US11312066B2 (en) * | 2017-03-27 | 2022-04-26 | Carbon, Inc. | Method of making three-dimensional objects by additive manufacturing |
| CN106947205A (zh) * | 2017-04-19 | 2017-07-14 | 塑成科技（北京）有限责任公司 | 一种立体光固化快速成型的耐高温光敏树脂及其制备方法 |
| US11283189B2 (en) | 2017-05-02 | 2022-03-22 | Rogers Corporation | Connected dielectric resonator antenna array and method of making the same |
| US11616302B2 (en) | 2018-01-15 | 2023-03-28 | Rogers Corporation | Dielectric resonator antenna having first and second dielectric portions |
| WO2019167895A1 (ja) * | 2018-03-01 | 2019-09-06 | コニカミノルタ株式会社 | 樹脂組成物、およびこれを用いた立体造形物の製造方法、ならびに立体造形物 |
| WO2019193961A1 (ja) * | 2018-04-02 | 2019-10-10 | コニカミノルタ株式会社 | 樹脂組成物、およびこれを用いた立体造形物の製造方法、ならびに立体造形物 |
| CN108559263B (zh) * | 2018-05-25 | 2020-11-10 | 黑龙江省科学院石油化学研究院 | 一种耐高温双马树脂复合材料表面膜及其制备方法 |
| CN108976788A (zh) * | 2018-06-05 | 2018-12-11 | 宁波市石生科技有限公司 | 一种耐高温三维制造材料及使用该材料制造三维物的方法 |
| US11945900B2 (en) | 2018-06-29 | 2024-04-02 | 3M Innovative Properties Company | Orthodontic articles prepared using a polycarbonate diol, polymerizable compositions, and methods of making the articles |
| US11407890B2 (en) | 2018-09-10 | 2022-08-09 | Carbon, Inc. | Dual cure additive manufacturing resins for production of flame retardant objects |
| US11552390B2 (en) | 2018-09-11 | 2023-01-10 | Rogers Corporation | Dielectric resonator antenna system |
| US11376799B2 (en) | 2018-09-28 | 2022-07-05 | Stratasys Ltd. | Method for additive manufacturing with partial curing |
| US11235511B2 (en) | 2018-09-28 | 2022-02-01 | Stratasys Ltd. | Three-dimensional inkjet printing of a thermally stable object |
| CN109280361B (zh) * | 2018-09-30 | 2021-02-26 | 嘉兴学院 | 一种热塑性弹性体材料及其制备方法 |
| CN109275983B (zh) * | 2018-09-30 | 2021-03-23 | 嘉兴学院 | 一种高柔性鞋垫及其制备方法 |
| EP3632941B1 (en) | 2018-10-01 | 2023-08-23 | Cubicure GmbH | Resin composition |
| TWI820237B (zh) | 2018-10-18 | 2023-11-01 | 美商羅傑斯公司 | 聚合物結構、其立體光刻製造方法以及包含該聚合物結構之電子裝置 |
| WO2020117489A1 (en) | 2018-12-04 | 2020-06-11 | Rogers Corporation | Dielectric electromagnetic structure and method of making the same |
| WO2020117407A1 (en) | 2018-12-07 | 2020-06-11 | Carbon, Inc. | Methods of surface finishing objects produced by additive manufacturing |
| KR20220016812A (ko) | 2019-05-30 | 2022-02-10 | 로저스코포레이션 | 스테레오리소그래피용 광경화성 조성물, 조성물을 사용한 스테레오리소그래피 방법, 스테레오리소그래피 방법에 의해 형성된 폴리머 성분, 및 폴리머 성분을 포함하는 장치 |
| US11602896B2 (en) * | 2019-08-14 | 2023-03-14 | Mighty Buildings, Inc. | 3D printing of a composite material via sequential dual-curing polymerization |
| CN112480324B (zh) * | 2019-09-11 | 2022-07-19 | 中国科学院福建物质结构研究所 | 一种制备光固化树脂的原料组合物、由其制备的光固化树脂及其应用 |
| CN114616087B (zh) * | 2019-10-17 | 2024-11-01 | 汉高股份有限及两合公司 | 实现具有优异性能的三维部件的增材制造方法 |
| US11619039B2 (en) | 2020-03-05 | 2023-04-04 | Mighty Buildings, Inc. | Three-dimensional printed building components and structures |
| US11482790B2 (en) | 2020-04-08 | 2022-10-25 | Rogers Corporation | Dielectric lens and electromagnetic device with same |
| KR102373393B1 (ko) * | 2020-06-02 | 2022-03-11 | 오스템임플란트 주식회사 | 서지컬 가이드용 광경화성 수지 조성물, 이로부터 제조된 서지컬 가이드 및 그의 제조방법 |
| US11970575B2 (en) | 2020-10-05 | 2024-04-30 | Alliance For Sustainable Energy, Llc | Bioderived recyclable epoxy-anhydride thermosetting polymers and resins |
| CN112280370B (zh) * | 2020-11-19 | 2022-05-17 | 中国科学院兰州化学物理研究所 | 一种3d打印氰酸酯墨水及其制备方法和应用 |
| US12084588B2 (en) | 2020-12-23 | 2024-09-10 | Formlabs, Inc. | Multi-component composition for additive manufacturing |
| EP4029675B1 (en) * | 2021-01-19 | 2024-05-29 | Bostik SA | 3d-printing methods and systems |
| CN113087852B (zh) * | 2021-04-26 | 2022-06-28 | 中国科学院兰州化学物理研究所 | 可4d打印氰酸酯形状记忆聚合物材料及其制备方法和氰酸酯形状记忆聚合物器件及其应用 |
| KR102737318B1 (ko) * | 2021-06-09 | 2024-12-04 | 알타나 뉴 테크놀로지스 게엠베하 | 이중 경화 시아네이트 에스테르 잉크젯 조성물 |
| US11352514B1 (en) | 2021-06-09 | 2022-06-07 | Altana New Technologies Gmbh | Dual-curable inkjet composition |
| US20240392154A1 (en) | 2022-01-18 | 2024-11-28 | Noga 3D Innovations Ltd | Dual-cure epoxy resins for 3d printing of high-performance materials |
| WO2023220523A1 (en) | 2022-05-09 | 2023-11-16 | Carbon, Inc. | Method for direct coloration of resins for additive manufacturing |
| EP4543963A1 (de) | 2022-06-23 | 2025-04-30 | Technische Universität Wien | Cyanatester als monomere in polymerisierbaren zusammensetzungen |
| CN116589883B (zh) * | 2023-06-20 | 2024-01-30 | 中国科学院兰州化学物理研究所 | 一种氰酸酯墨水及其制备方法、氰酸酯形状记忆材料和应用 |
| WO2025080931A1 (en) | 2023-10-12 | 2025-04-17 | Carbon, Inc. | Dual cure resins for mixed modulus materials |
Family Cites Families (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1251023B (de) | 1965-05-26 | 1967-09-28 | Farbenfabriken Bayer Aktienge Seilschaft Leverkusen | Verfahren zur Herstellung von aromatischen Cyansaureestern |
| DE2628417C2 (de) | 1976-06-24 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Härtbare Mischungen |
| JPS5626951A (en) | 1979-08-08 | 1981-03-16 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
| JPS5626950A (en) | 1979-08-08 | 1981-03-16 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
| JPS5626911A (en) | 1979-08-08 | 1981-03-16 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
| US4421822A (en) | 1979-08-20 | 1983-12-20 | Minnesota Mining And Manufacturing Co. | Ultraviolet polymerization of acrylate monomers using oxidizable tin compounds |
| JPS56110760A (en) | 1980-02-06 | 1981-09-02 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
| JPS56141321A (en) | 1980-04-08 | 1981-11-05 | Mitsubishi Gas Chem Co Inc | Photosetting resin composition |
| US4389514A (en) | 1980-09-26 | 1983-06-21 | Congoleum Corporation | Accelerated polymerization of acrylic monomers initiated by dialkyl and diaralkyl peroxide free radical generators in the presence of tin accelerators |
| US4740583A (en) | 1984-05-11 | 1988-04-26 | General Electric Company | Method for converting cyclic polycarbonate oligomer mixtures to linear polycarbonate, and composition resulting therefrom |
| US5236637A (en) | 1984-08-08 | 1993-08-17 | 3D Systems, Inc. | Method of and apparatus for production of three dimensional objects by stereolithography |
| US4600760A (en) | 1984-08-09 | 1986-07-15 | The Dow Chemical Company | Thermosettable resin composition containing alkenyl phenyl cyanate |
| US4604452A (en) | 1985-10-21 | 1986-08-05 | Celanese Corporation | Metal carboxylate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols |
| US4775741A (en) | 1986-07-21 | 1988-10-04 | General Electric Company | Preparation of resin composition from cyclic polycarbonate oligomers from spirobiindane bisphenol |
| US4757132A (en) | 1986-10-20 | 1988-07-12 | General Electric Company | Cyclic polyester oligomer polymerization |
| AU597435B2 (en) | 1986-11-24 | 1990-05-31 | Ciba-Geigy Ag | Low viscosity noncrystalline dicyanate esters and blends with prepolymers of dicyanate esters |
| US4785075A (en) | 1987-07-27 | 1988-11-15 | Interez, Inc. | Metal acetylacetonate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols |
| US4847233A (en) | 1987-07-27 | 1989-07-11 | Hi-Tek Polymers, Inc. | Metal acetylacetonate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols |
| JPH0757532B2 (ja) | 1988-10-19 | 1995-06-21 | 松下電工株式会社 | 三次元形状の形成方法 |
| US5248456A (en) | 1989-06-12 | 1993-09-28 | 3D Systems, Inc. | Method and apparatus for cleaning stereolithographically produced objects |
| US5093385A (en) | 1989-12-21 | 1992-03-03 | Minnesota Mining And Manufacturing Company | Method of accelerating photoiniferter polymerization, polymer produced thereby, and product produced therewith |
| DE4004620C1 (en) | 1990-02-15 | 1991-09-05 | Du Pont De Nemours (Deutschland) Gmbh, 6380 Bad Homburg, De | Photo-structured layer of three=dimensional object prodn. - by using fusible plastisol or organosol contg. unsatd. monomer, photoinitiator and thermally reactive cpd. |
| US5158858A (en) | 1990-07-05 | 1992-10-27 | E. I. Du Pont De Nemours And Company | Solid imaging system using differential tension elastomeric film |
| US5143785A (en) | 1990-08-20 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Cyanate ester adhesives for electronic applications |
| US5122441A (en) | 1990-10-29 | 1992-06-16 | E. I. Du Pont De Nemours And Company | Method for fabricating an integral three-dimensional object from layers of a photoformable composition |
| US5466744A (en) | 1990-11-05 | 1995-11-14 | General Electric Company | Polymerization of macrocyclic poly(alkylene dicarboxylate) oligomers |
| EP0525578A1 (en) | 1991-08-02 | 1993-02-03 | E.I. Du Pont De Nemours And Company | Photopolymer composition for the production of three-dimensional objects |
| EP0579503B1 (en) | 1992-07-17 | 1997-11-05 | Ethicon Inc. | Radiation-curable, urethane-acrylate prepolymers and crosslinked polymers |
| US5264061A (en) | 1992-10-22 | 1993-11-23 | Motorola, Inc. | Method of forming a three-dimensional printed circuit assembly |
| US5679719A (en) | 1993-03-24 | 1997-10-21 | Loctite Corporation | Method of preparing fiber/resin composites |
| US5744557A (en) | 1993-06-16 | 1998-04-28 | Minnesota Mining And Manufacturing Company | Energy-curable cyanate/ethylenically unsaturated compositions |
| EP0643329B2 (de) | 1993-08-26 | 2002-02-06 | Vantico AG | Flüssige strahlungshärtbare Zusammensetzung, insbesondere für die Stereolithographie |
| US5543516A (en) | 1994-05-18 | 1996-08-06 | Edison Polymer Innovation Corporation | Process for preparation of benzoxazine compounds in solventless systems |
| US5705116A (en) * | 1994-06-27 | 1998-01-06 | Sitzmann; Eugene Valentine | Increasing the useful range of cationic photoinitiators in stereolithography |
| IL112140A (en) | 1994-12-25 | 1997-07-13 | Cubital Ltd | Method of forming three dimensional objects |
| US5494981A (en) | 1995-03-03 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Epoxy-cyanate ester compositions that form interpenetrating networks via a Bronsted acid |
| US5707780A (en) | 1995-06-07 | 1998-01-13 | E. I. Du Pont De Nemours And Company | Photohardenable epoxy composition |
| US5498651A (en) | 1995-06-19 | 1996-03-12 | General Electric Company | Method for polymerizing macrocyclic polyester oligomers |
| JP3498439B2 (ja) * | 1995-08-04 | 2004-02-16 | 住友電気工業株式会社 | 硬化性樹脂組成物とそれを用いた成形体およびその製造方法 |
| EP0945755B1 (en) | 1998-03-25 | 2002-06-05 | Agfa-Gevaert | A photosensitive image-forming element containing silver halide cristals internally modified with a metal-halogen-fluorine complex |
| US6154596A (en) * | 1998-03-26 | 2000-11-28 | Hughes Electronics Corporation | Front end preparation procedure for efficient coupling and improved power handling of light into a multi-mode fiber |
| KR100339183B1 (ko) * | 1998-07-13 | 2002-05-31 | 포만 제프리 엘 | 접착제 번짐이 감소된 다이 부착법 |
| US6207786B1 (en) | 1998-11-10 | 2001-03-27 | Edison Polymer Innovation Corporation | Ternary systems of benzoxazine, epoxy, and phenolic resins |
| US6632893B2 (en) | 1999-05-28 | 2003-10-14 | Henkel Loctite Corporation | Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners |
| US6658314B1 (en) | 1999-10-06 | 2003-12-02 | Objet Geometries Ltd. | System and method for three dimensional model printing |
| DE19961926A1 (de) | 1999-12-22 | 2001-07-05 | Basf Coatings Ag | Thermisch mit aktinischer Strahlung härtbare Stoffgemische und ihre Verwendung |
| JP2003522821A (ja) * | 2000-02-08 | 2003-07-29 | バンティコ アクチエンゲゼルシャフト | 特にステレオリソグラフィーのための液状放射線硬化性組成物 |
| US7300619B2 (en) | 2000-03-13 | 2007-11-27 | Objet Geometries Ltd. | Compositions and methods for use in three dimensional model printing |
| US6309797B1 (en) | 2000-04-26 | 2001-10-30 | Spectra Group Limited, Inc. | Selectively colorable polymerizable compositions |
| FR2809741B1 (fr) | 2000-05-31 | 2002-08-16 | Atofina | Materiaux thermodurs a tenue au choc amelioree |
| JP4382978B2 (ja) | 2000-12-04 | 2009-12-16 | 学校法人神奈川大学 | 光硬化性・熱硬化性樹脂組成物 |
| DE10115505B4 (de) | 2001-03-29 | 2007-03-08 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbare wäßrige Dispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10119817A1 (de) | 2001-04-23 | 2002-10-24 | Envision Technologies Gmbh | Vorrichtung und Verfahren für die zerstörungsfreie Trennung ausgehärteter Materialschichten von einer planen Bauebene |
| US6709738B2 (en) | 2001-10-15 | 2004-03-23 | 3M Innovative Properties Company | Coated substrate with energy curable cyanate resin |
| US6620905B1 (en) | 2002-02-23 | 2003-09-16 | National Starch And Chemical Investment Holding Corporation | Curable compositions containing benzoxazine |
| US6861475B2 (en) | 2002-10-16 | 2005-03-01 | Rohm And Haas Company | Smooth, flexible powder coatings |
| CA2789741C (en) | 2003-06-09 | 2014-11-04 | Kaneka Corporation | Process for producing modified epoxy resin |
| KR101474174B1 (ko) | 2004-03-22 | 2014-12-17 | 3디 시스템즈 인코오퍼레이티드 | 광경화성 조성물 |
| US7642316B2 (en) | 2004-10-14 | 2010-01-05 | Dow Global Technologies, Inc. | Rubber modified monovinylidene aromatic polymers and fabricated articles prepared therefrom |
| WO2006045002A2 (en) | 2004-10-19 | 2006-04-27 | Rolls-Royce Corporation | Method and apparatus associated with anisotropic shrink in sintered ceramic items |
| MX2007005599A (es) | 2004-11-10 | 2007-05-23 | Dow Global Technologies Inc | Resinas epoxicas modificadas con copolimero de bloque anfifilico y adhesivos hechos a partir de las mismas. |
| EP1941322B1 (en) * | 2005-10-27 | 2018-05-30 | 3D Systems, Inc. | Antimony-free photocurable resin composition and three dimensional article |
| WO2007056561A2 (en) | 2005-11-09 | 2007-05-18 | Liquidia Technologies, Inc. | Medical device, materials, and methods |
| US8591516B2 (en) | 2006-02-27 | 2013-11-26 | Biomet Manufacturing, Llc | Patient-specific orthopedic instruments |
| US8092465B2 (en) | 2006-06-09 | 2012-01-10 | Biomet Manufacturing Corp. | Patient specific knee alignment guide and associated method |
| US20080103226A1 (en) | 2006-10-31 | 2008-05-01 | Dsm Ip Assets B.V. | Photo-curable resin composition |
| US7892474B2 (en) | 2006-11-15 | 2011-02-22 | Envisiontec Gmbh | Continuous generative process for producing a three-dimensional object |
| US8128393B2 (en) | 2006-12-04 | 2012-03-06 | Liquidia Technologies, Inc. | Methods and materials for fabricating laminate nanomolds and nanoparticles therefrom |
| EP2123711B1 (en) | 2007-02-28 | 2016-12-14 | Kaneka Corporation | Thermosetting resin composition having rubbery polymer particle dispersed therein, and process for production thereof |
| JP4863288B2 (ja) * | 2007-03-20 | 2012-01-25 | Ｊｓｒ株式会社 | 光学的立体造形用光硬化性樹脂組成物及び立体造形物 |
| US20100227941A1 (en) | 2007-03-20 | 2010-09-09 | Dsm Ip Assets B.V. | Stereolithography resin compositions and three-dimensional objects made therefrom |
| EP2145231B1 (en) | 2007-04-03 | 2011-09-14 | Basf Se | Photoactivable nitrogen bases |
| WO2008127925A2 (en) | 2007-04-11 | 2008-10-23 | Dow Global Technologies, Inc. | Structural epoxy resins containing core-shell rubbers |
| EP2344561B1 (en) | 2007-06-20 | 2015-07-29 | Dow Global Technologies LLC | Crash durable epoxy adhesives with very low sensitivity to temperature variations |
| EP2052693B2 (en) | 2007-10-26 | 2021-02-17 | Envisiontec GmbH | Process and freeform fabrication system for producing a three-dimensional object |
| US20100280151A1 (en) | 2009-05-04 | 2010-11-04 | Toray Industries, Inc. | Toughened fiber reinforced polymer composite with core-shell particles |
| EP2493396B1 (en) | 2009-10-29 | 2016-11-23 | Zimmer, Inc. | Patient-specific mill guide |
| KR101995185B1 (ko) | 2009-12-17 | 2019-07-01 | 디에스엠 아이피 어셋츠 비.브이. | 트라이아릴 설포늄 보레이트 양이온 광개시제를 포함하는 적층식 제작을 위한 액체 방사선 경화성 수지 |
| US8632547B2 (en) | 2010-02-26 | 2014-01-21 | Biomet Sports Medicine, Llc | Patient-specific osteotomy devices and methods |
| US9066727B2 (en) | 2010-03-04 | 2015-06-30 | Materialise Nv | Patient-specific computed tomography guides |
| WO2011160008A1 (en) | 2010-06-18 | 2011-12-22 | Howmedica Osteonics Corp. | Patient-specific total hip arthroplasty |
| WO2012033483A1 (en) * | 2010-09-07 | 2012-03-15 | 3M Innovative Properties Company | Curable resin composition and multi-layer laminate manufactured using the same |
| US8801418B2 (en) | 2011-01-31 | 2014-08-12 | Global Filtration Systems | Method and apparatus for making three-dimensional objects from multiple solidifiable materials |
| US9186154B2 (en) | 2011-03-17 | 2015-11-17 | Zimmer, Inc. | Patient-specific instruments for total ankle arthroplasty |
| US8715289B2 (en) | 2011-04-15 | 2014-05-06 | Biomet Manufacturing, Llc | Patient-specific numerically controlled instrument |
| US9066734B2 (en) | 2011-08-31 | 2015-06-30 | Biomet Manufacturing, Llc | Patient-specific sacroiliac guides and associated methods |
| KR20130066527A (ko) | 2011-12-12 | 2013-06-20 | 주식회사 엘지화학 | 연성 금속박 적층판 |
| US9120270B2 (en) | 2012-04-27 | 2015-09-01 | University Of Southern California | Digital mask-image-projection-based additive manufacturing that applies shearing force to detach each added layer |
| US9636873B2 (en) | 2012-05-03 | 2017-05-02 | B9Creations, LLC | Solid image apparatus with improved part separation from the image plate |
| US10271886B2 (en) | 2012-07-23 | 2019-04-30 | Zimmer, Inc. | Patient-specific instrumentation for implant revision surgery |
| WO2014035655A2 (en) | 2012-08-27 | 2014-03-06 | Dow Global Technologies Llc | Accelerated and toughened two part epoxy adhesives |
| RU2605985C2 (ru) | 2012-09-17 | 2017-01-10 | 3М Инновейтив Пропертиз Компани | Порошковые эпоксидные композиции для покрытий, способы и изделия |
| US9060788B2 (en) | 2012-12-11 | 2015-06-23 | Biomet Manufacturing, Llc | Patient-specific acetabular guide for anterior approach |
| EP2757118A1 (en) | 2013-01-17 | 2014-07-23 | Allnex Belgium, S.A. | Radiation curable aqueous compositions with reversible drying. |
| CN105122136B (zh) * | 2013-02-12 | 2020-03-24 | 卡本有限公司 | 三维制造的方法和设备 |
| EP3203318A1 (en) | 2013-02-12 | 2017-08-09 | CARBON3D, Inc. | Continuous liquid interphase printing |
| US9360757B2 (en) * | 2013-08-14 | 2016-06-07 | Carbon3D, Inc. | Continuous liquid interphase printing |
| CN103571211A (zh) | 2013-10-13 | 2014-02-12 | 甘春丽 | 双重固化组合物 |
| JP6433651B2 (ja) | 2013-11-21 | 2018-12-05 | スリーエム イノベイティブ プロパティズ カンパニー | 接着剤、接着剤付部材及び部材間の接続方法 |
| US9654377B2 (en) | 2014-01-30 | 2017-05-16 | Thomson Licensing | Per port ethernet packet processing mode by device type |
| WO2015164234A1 (en) | 2014-04-25 | 2015-10-29 | Carbon3D, Inc. | Continuous three dimensional fabrication from immiscible liquids |
| EP3158398B1 (en) | 2014-06-23 | 2024-09-04 | Carbon, Inc. | Methods of producing polyurethane three-dimensional objects from materials having multiple mechanisms of hardening |
| US9574039B1 (en) | 2014-07-22 | 2017-02-21 | Full Spectrum Laser | Additive use in photopolymer resin for 3D printing to enhance the appearance of printed parts |
| WO2016126779A1 (en) * | 2015-02-05 | 2016-08-11 | Carbon3D, Inc. | Method of additive manufacturing by fabrication through multiple zones |
| US9708440B2 (en) | 2015-06-18 | 2017-07-18 | Novoset, Llc | High temperature three dimensional printing compositions |
-
2016
- 2016-09-02 EP EP16766748.4A patent/EP3344676B1/en active Active
- 2016-09-02 CN CN201680051002.0A patent/CN108350145B/zh active Active
- 2016-09-02 JP JP2018511267A patent/JP7069006B2/ja active Active
- 2016-09-02 US US15/754,086 patent/US10471655B2/en active Active
- 2016-09-02 WO PCT/US2016/050035 patent/WO2017040883A1/en not_active Ceased
-
2019
- 2019-09-20 US US16/576,862 patent/US11090859B2/en active Active
- 2019-09-20 US US16/576,844 patent/US11040483B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018527442A5 (cg-RX-API-DMAC7.html) | ||
| Berger et al. | Halogen bonding in polymer science: from crystal engineering to functional supramolecular polymers and materials | |
| Wan et al. | Learning about novel amine-adduct curing agents for epoxy resins: butyl-glycidylether-modified poly (propyleneimine) dendrimers | |
| JP6710434B2 (ja) | シアン酸エステル化合物、該化合物を含む硬化性樹脂組成物及びその硬化物 | |
| WO2014065422A1 (ja) | ハロゲン化シアンの製造方法、シアン酸エステル化合物及びその製造方法、並びに樹脂組成物 | |
| JP6602016B2 (ja) | シアン酸エステル化合物、該化合物を含む硬化性樹脂組成物及びその硬化物 | |
| TW200829545A (en) | Monomers comprising superacidic groups, and polymers therefrom | |
| TW201237067A (en) | Curable resin composition and cured product thereof | |
| CN103274908B (zh) | 一种含双叔丁基和芴基结构的双酚单体及其制备方法和应用 | |
| Shustova et al. | Sc3N@(C80-I h (7))(CF3) 14 and Sc3N@(C80-I h (7))(CF3) 16. Endohedral Metallofullerene Derivatives with Exohedral Addends on Four and Eight Triple-Hexagon Junctions. Does the Sc3N Cluster Control the Addition Pattern or Vice Versa? | |
| KR20100134018A (ko) | 지방족 탄소 함량이 높은 방향족 디시아네이트 화합물 | |
| Khoshsefat et al. | From tetramerization to oligomerization/polymerization of ethylene by dinuclear pyridyl‐imine Co‐and Ni‐based catalysts | |
| JP2010538134A5 (cg-RX-API-DMAC7.html) | ||
| Liu et al. | Storage stability and curing behavior of epoxy‐dicyandiamide systems with carbonyldiimidazole‐Cu (II) complexes as the accelerator | |
| JP2018168085A (ja) | シアン酸エステル化合物、樹脂組成物、硬化物、構造材料用プリプレグ、封止用材料、繊維強化複合材料及び接着剤 | |
| Omrani et al. | Kinetic modeling of ring-opening polymerization of benzoxazines using MIL-53-Al as a potent catalyst | |
| Hu et al. | Self-curing phthalonitrile resin with disulfide bond as the curing group | |
| Iguchi et al. | Application of Benzoxazine‐Based Dimers, Oligomers, and Polymers as Chelating Agents | |
| JP6325729B1 (ja) | エポキシ樹脂組成物および硬化物 | |
| WO2017196805A1 (en) | Benzothiazoles as latent catalysts for benzoxazine resins | |
| Zhang et al. | Computer-aided screening of Benzoxazines with high thermal stability and good processability | |
| US9481743B2 (en) | Polyelectrolyte polymers, their manufacture and use | |
| JP6667126B2 (ja) | シアン酸エステル化合物、該化合物を含む硬化性樹脂組成物及びその硬化物 | |
| Qin et al. | Synthesis of aromatic amine curing agent containing non-coplanar rigid moieties and its curing kinetics with epoxy resin | |
| Wan et al. | Synthesis and nonisothermal reaction of a novel acrylonitrile-capped poly (propyleneimine) dendrimer with epoxy resin |