JPWO2021048628A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2021048628A5 JPWO2021048628A5 JP2022516133A JP2022516133A JPWO2021048628A5 JP WO2021048628 A5 JPWO2021048628 A5 JP WO2021048628A5 JP 2022516133 A JP2022516133 A JP 2022516133A JP 2022516133 A JP2022516133 A JP 2022516133A JP WO2021048628 A5 JPWO2021048628 A5 JP WO2021048628A5
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- meth
- propan
- monomer
- formula
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 claims 29
- -1 Poly(oxy-1,2-ethanediyl) Polymers 0.000 claims 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 21
- 239000000178 monomer Substances 0.000 claims 18
- 239000000843 powder Substances 0.000 claims 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 9
- 239000000919 ceramic Substances 0.000 claims 6
- 239000002270 dispersing agent Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 5
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- 238000010146 3D printing Methods 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 239000002245 particle Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000004014 plasticizer Substances 0.000 claims 3
- NIAXWFTYAJQENP-UHFFFAOYSA-N 3-ethenyl-2h-1,3-oxazole Chemical compound C=CN1COC=C1 NIAXWFTYAJQENP-UHFFFAOYSA-N 0.000 claims 2
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims 2
- HSPRVWPULGKMRC-UHFFFAOYSA-N 57526-50-8 Chemical compound C12CCCC2C2CC(CO)C1C2 HSPRVWPULGKMRC-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 239000005062 Polybutadiene Substances 0.000 claims 2
- 239000002202 Polyethylene glycol Chemical class 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 229910021389 graphene Inorganic materials 0.000 claims 2
- 229920000592 inorganic polymer Polymers 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims 2
- 150000004767 nitrides Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229920002857 polybutadiene Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 229910021332 silicide Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- VCOKAARWPAHHHY-UHFFFAOYSA-N (1-phenoxy-3-phenylsulfanylpropan-2-yl) prop-2-enoate Chemical compound C=1C=CC=CC=1SCC(OC(=O)C=C)COC1=CC=CC=C1 VCOKAARWPAHHHY-UHFFFAOYSA-N 0.000 claims 1
- RCTZKJGLWRCHMI-UHFFFAOYSA-N (2-ethylphenyl) 2-methylprop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C(C)=C RCTZKJGLWRCHMI-UHFFFAOYSA-N 0.000 claims 1
- HYZJSTPCAKOIHY-UHFFFAOYSA-N (2-ethylphenyl) prop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C=C HYZJSTPCAKOIHY-UHFFFAOYSA-N 0.000 claims 1
- QJVFGKGOBVWBFI-UHFFFAOYSA-N (2-hexylphenyl) 2-methylprop-2-eneperoxoate Chemical compound CCCCCCC1=CC=CC=C1OOC(=O)C(C)=C QJVFGKGOBVWBFI-UHFFFAOYSA-N 0.000 claims 1
- YZKWZGWPAHAZDU-UHFFFAOYSA-N (2-hexylphenyl) prop-2-eneperoxoate Chemical class CCCCCCC1=CC=CC=C1OOC(=O)C=C YZKWZGWPAHAZDU-UHFFFAOYSA-N 0.000 claims 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 1
- AOUAMFARIYTDLK-UHFFFAOYSA-N (4-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1 AOUAMFARIYTDLK-UHFFFAOYSA-N 0.000 claims 1
- ZALFZMYXGFDRIW-UHFFFAOYSA-N (4-methylphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(C)C=C1 ZALFZMYXGFDRIW-UHFFFAOYSA-N 0.000 claims 1
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- QPNYYEXYBPEGLD-UHFFFAOYSA-N 1,3-bis(1,3-benzothiazol-2-ylsulfanyl)propan-2-yl prop-2-enoate Chemical compound C1=CC=C2SC(SCC(CSC=3SC4=CC=CC=C4N=3)OC(=O)C=C)=NC2=C1 QPNYYEXYBPEGLD-UHFFFAOYSA-N 0.000 claims 1
- BWCGUOCSDMXYRG-UHFFFAOYSA-N 1,3-bis(2,4,6-tribromophenoxy)propan-2-yl prop-2-enoate Chemical compound BrC1=CC(Br)=CC(Br)=C1OCC(OC(=O)C=C)COC1=C(Br)C=C(Br)C=C1Br BWCGUOCSDMXYRG-UHFFFAOYSA-N 0.000 claims 1
- IHEKHPVOKFNGJS-UHFFFAOYSA-N 1,3-bis(2-bromophenoxy)propan-2-yl prop-2-enoate Chemical compound BrC1=CC=CC=C1OCC(OC(=O)C=C)COC1=CC=CC=C1Br IHEKHPVOKFNGJS-UHFFFAOYSA-N 0.000 claims 1
- YRZHSSDJIKPZNH-UHFFFAOYSA-N 1,3-bis(2-phenylsulfanylethylsulfanyl)propan-2-yl prop-2-enoate Chemical compound C=1C=CC=CC=1SCCSCC(OC(=O)C=C)CSCCSC1=CC=CC=C1 YRZHSSDJIKPZNH-UHFFFAOYSA-N 0.000 claims 1
- VRRHAQBJOFBLML-UHFFFAOYSA-N 1,3-bis(2-sulfanylidene-3H-1,3-benzothiazol-4-yl)propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(CC1=C2C(=CC=C1)SC(=S)N2)CC3=C4C(=CC=C3)SC(=S)N4 VRRHAQBJOFBLML-UHFFFAOYSA-N 0.000 claims 1
- QGOGKTYXIXZJPH-UHFFFAOYSA-N 1,3-bis(3-bromophenoxy)propan-2-yl prop-2-enoate Chemical compound BrC1=CC=CC(OCC(COC=2C=C(Br)C=CC=2)OC(=O)C=C)=C1 QGOGKTYXIXZJPH-UHFFFAOYSA-N 0.000 claims 1
- XXUMEQVGZIPCJQ-UHFFFAOYSA-N 1,3-bis(4-bromophenoxy)propan-2-yl prop-2-enoate Chemical compound C1=CC(Br)=CC=C1OCC(OC(=O)C=C)COC1=CC=C(Br)C=C1 XXUMEQVGZIPCJQ-UHFFFAOYSA-N 0.000 claims 1
- GEOYSVNNOUCERG-UHFFFAOYSA-N 1,3-bis(phenylsulfanyl)propan-2-yl prop-2-enoate Chemical compound C=1C=CC=CC=1SCC(OC(=O)C=C)CSC1=CC=CC=C1 GEOYSVNNOUCERG-UHFFFAOYSA-N 0.000 claims 1
- WRTGATGOTHMVOB-UHFFFAOYSA-N 1,3-bis[(2,4,6-tribromophenyl)sulfanyl]propan-2-yl prop-2-enoate Chemical compound BrC1=CC(Br)=CC(Br)=C1SCC(OC(=O)C=C)CSC1=C(Br)C=C(Br)C=C1Br WRTGATGOTHMVOB-UHFFFAOYSA-N 0.000 claims 1
- PJWHZDQZFVYBSX-UHFFFAOYSA-N 1,3-bis[(3-bromophenyl)sulfanyl]propan-2-yl prop-2-enoate Chemical compound BrC1=CC=CC(SCC(CSC=2C=C(Br)C=CC=2)OC(=O)C=C)=C1 PJWHZDQZFVYBSX-UHFFFAOYSA-N 0.000 claims 1
- AGLGRYPIZGGWDE-UHFFFAOYSA-N 1,3-bis[(4-bromophenyl)sulfanyl]propan-2-yl prop-2-enoate Chemical compound C1=CC(Br)=CC=C1SCC(OC(=O)C=C)CSC1=CC=C(Br)C=C1 AGLGRYPIZGGWDE-UHFFFAOYSA-N 0.000 claims 1
- AMCFKQHMQZMFQD-UHFFFAOYSA-N 1,3-bis[(4-methylphenyl)sulfanyl]propan-2-yl prop-2-enoate Chemical compound C1=CC(C)=CC=C1SCC(OC(=O)C=C)CSC1=CC=C(C)C=C1 AMCFKQHMQZMFQD-UHFFFAOYSA-N 0.000 claims 1
- GBQPKDQGWLHMIT-UHFFFAOYSA-N 1,3-di(phenothiazin-10-yl)propan-2-yl prop-2-enoate Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC(OC(=O)C=C)CN1C2=CC=CC=C2SC2=CC=CC=C21 GBQPKDQGWLHMIT-UHFFFAOYSA-N 0.000 claims 1
- XUVCISVDXYDUTO-UHFFFAOYSA-N 1,3-diphenoxypropan-2-yl prop-2-enoate Chemical compound C=1C=CC=CC=1OCC(OC(=O)C=C)COC1=CC=CC=C1 XUVCISVDXYDUTO-UHFFFAOYSA-N 0.000 claims 1
- ITKPEKLPFWJSOJ-UHFFFAOYSA-N 2-(2-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1Cl ITKPEKLPFWJSOJ-UHFFFAOYSA-N 0.000 claims 1
- YEQRGDXTQPUPMJ-UHFFFAOYSA-N 2-(2-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1C YEQRGDXTQPUPMJ-UHFFFAOYSA-N 0.000 claims 1
- VAZQKPWSBFZARZ-UHFFFAOYSA-N 2-(2-phenylphenoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1C1=CC=CC=C1 VAZQKPWSBFZARZ-UHFFFAOYSA-N 0.000 claims 1
- CAWQOFMAJKVFII-UHFFFAOYSA-N 2-(3-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(Cl)=C1 CAWQOFMAJKVFII-UHFFFAOYSA-N 0.000 claims 1
- JPTHRABUTMVMHR-UHFFFAOYSA-N 2-(3-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C)=C1 JPTHRABUTMVMHR-UHFFFAOYSA-N 0.000 claims 1
- ACZLUEDVQBUFQM-UHFFFAOYSA-N 2-(3-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C=2C=CC=CC=2)=C1 ACZLUEDVQBUFQM-UHFFFAOYSA-N 0.000 claims 1
- XUXKNMQGQVAAJA-UHFFFAOYSA-N 2-(4-benzylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1CC1=CC=CC=C1 XUXKNMQGQVAAJA-UHFFFAOYSA-N 0.000 claims 1
- XHMBRNYBXTUYJN-UHFFFAOYSA-N 2-(4-bromophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Br)C=C1 XHMBRNYBXTUYJN-UHFFFAOYSA-N 0.000 claims 1
- DANPNQMLVGTTRA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Cl)C=C1 DANPNQMLVGTTRA-UHFFFAOYSA-N 0.000 claims 1
- WRAODFTZIJZVJH-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1CCCCC1 WRAODFTZIJZVJH-UHFFFAOYSA-N 0.000 claims 1
- IOFBPLNRQQDCSU-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl 2-methylprop-2-enoate Chemical compound COC1=CC=C(CCOC(=O)C(C)=C)C=C1 IOFBPLNRQQDCSU-UHFFFAOYSA-N 0.000 claims 1
- HKGJTSSOXHQYDQ-UHFFFAOYSA-N 2-(4-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(C)C=C1 HKGJTSSOXHQYDQ-UHFFFAOYSA-N 0.000 claims 1
- XKTDLXROKPMKQF-UHFFFAOYSA-N 2-(4-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1=CC=CC=C1 XKTDLXROKPMKQF-UHFFFAOYSA-N 0.000 claims 1
- VZHXURTZSGZTOY-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(C)C1=CC=C(CCOC(=O)C(C)=C)C=C1 VZHXURTZSGZTOY-UHFFFAOYSA-N 0.000 claims 1
- WIGVBGZTCYJIIS-UHFFFAOYSA-N 2-(4-propylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(CCOC(=O)C(C)=C)C=C1 WIGVBGZTCYJIIS-UHFFFAOYSA-N 0.000 claims 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- GPMFRNBDJSNABI-UHFFFAOYSA-N [1-(2,4,6-tribromophenoxy)-3-(2,4,6-tribromophenyl)sulfanylpropan-2-yl] prop-2-enoate Chemical compound BrC1=CC(Br)=CC(Br)=C1OCC(OC(=O)C=C)CSC1=C(Br)C=C(Br)C=C1Br GPMFRNBDJSNABI-UHFFFAOYSA-N 0.000 claims 1
- KYDFEUGUOJUMED-UHFFFAOYSA-N [1-(4-bromophenoxy)-3-(4-bromophenyl)sulfanylpropan-2-yl] prop-2-enoate Chemical compound C1=CC(Br)=CC=C1OCC(OC(=O)C=C)CSC1=CC=C(Br)C=C1 KYDFEUGUOJUMED-UHFFFAOYSA-N 0.000 claims 1
- FLAXZCSAJHEAOB-UHFFFAOYSA-N [1-(4-chlorophenoxy)-3-phenylsulfanylpropan-2-yl] prop-2-enoate Chemical compound C1=CC(Cl)=CC=C1OCC(OC(=O)C=C)CSC1=CC=CC=C1 FLAXZCSAJHEAOB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 239000002134 carbon nanofiber Substances 0.000 claims 1
- 239000002041 carbon nanotube Substances 0.000 claims 1
- 229910021393 carbon nanotube Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 229910003460 diamond Inorganic materials 0.000 claims 1
- 239000010432 diamond Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001247 metal acetylides Chemical class 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001400 nonyl 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])[H] 0.000 claims 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- LCDOENXNMQXGFS-UHFFFAOYSA-N phenoxybenzene;prop-2-enoic acid Chemical compound OC(=O)C=C.C=1C=CC=CC=1OC1=CC=CC=C1 LCDOENXNMQXGFS-UHFFFAOYSA-N 0.000 claims 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 1
- 125000005498 phthalate group Chemical class 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052715 tantalum Inorganic materials 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962899182P | 2019-09-12 | 2019-09-12 | |
| US62/899,182 | 2019-09-12 | ||
| PCT/IB2020/000754 WO2021048628A1 (en) | 2019-09-12 | 2020-09-11 | Photo-curable compositions containing high refractive index monomers for use in 3d printing applications |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022548052A JP2022548052A (ja) | 2022-11-16 |
| JP2022548052A5 JP2022548052A5 (https=) | 2023-08-31 |
| JPWO2021048628A5 true JPWO2021048628A5 (https=) | 2023-08-31 |
Family
ID=73013764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022516133A Pending JP2022548052A (ja) | 2019-09-12 | 2020-09-11 | ３ｄプリンティング用途における使用のための高屈折率モノマーを含有する光硬化性組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US12492275B2 (https=) |
| EP (1) | EP4028480A1 (https=) |
| JP (1) | JP2022548052A (https=) |
| KR (1) | KR20220062041A (https=) |
| CN (1) | CN114651049A (https=) |
| IL (1) | IL291203A (https=) |
| TW (1) | TWI842949B (https=) |
| WO (1) | WO2021048628A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220153693A1 (en) * | 2020-11-13 | 2022-05-19 | Facebook Technologies, Llc | Substituted mono- and poly-phenyl-core monomers and polymers thereof for volume bragg gratings |
| CN113077921B (zh) * | 2021-03-23 | 2024-03-19 | 深圳市宁鹏时代科技有限公司 | 生物微流控芯片3d打印电极材料与3d打印电极及其制备方法 |
| CN117280002A (zh) * | 2021-05-07 | 2023-12-22 | 巴斯夫欧洲公司 | 产生用于3d光聚合物喷射的支撑子结构的可辐射固化组合物 |
| CN113968734B (zh) * | 2021-11-15 | 2022-08-16 | 重庆文理学院 | 一种高致密度氧化锆陶瓷材料的制备方法 |
| CN113896528B (zh) * | 2021-11-15 | 2022-07-26 | 重庆文理学院 | 一种dlp-3d打印制备高性能氧化锆陶瓷材料的方法 |
| CN114368972B (zh) * | 2022-01-21 | 2023-02-28 | 中国地质大学（武汉） | 可见光3d打印光固化陶瓷浆料、制备方法及打印方法 |
| CN115385834B (zh) * | 2022-08-15 | 2023-11-03 | 中国科学院理化技术研究所 | 一种高折射率树枝状（甲基）丙烯酸酯类单体及其制备方法和应用 |
| TW202421415A (zh) * | 2022-09-12 | 2024-06-01 | 新加坡國立大學 | 用於積層製造的漿料 |
| CN115572163B (zh) * | 2022-09-27 | 2023-04-25 | 河南驼人医疗器械研究院有限公司 | 一种提高光固化打印精度及力学性能的氧化锆陶瓷浆料及其制备方法 |
| JP2026502083A (ja) * | 2022-12-09 | 2026-01-21 | スリーディー システムズ インコーポレーテッド | 高い弾性率および分散安定性を有する３ｄプリント用のインク |
| KR102920961B1 (ko) * | 2023-06-30 | 2026-02-02 | 국립목포대학교산학협력단 | 디지털 라이트 프로세싱 3d 프린터용 슬러리 조성물 및 이를 이용한 지르코니아 소결체 제조방법 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496682A (en) | 1993-10-15 | 1996-03-05 | W. R. Grace & Co.-Conn. | Three dimensional sintered inorganic structures using photopolymerization |
| US6117612A (en) | 1995-04-24 | 2000-09-12 | Regents Of The University Of Michigan | Stereolithography resin for rapid prototyping of ceramics and metals |
| US6283997B1 (en) | 1998-11-13 | 2001-09-04 | The Trustees Of Princeton University | Controlled architecture ceramic composites by stereolithography |
| US6281319B1 (en) * | 1999-04-12 | 2001-08-28 | Surgidev Corporation | Water plasticized high refractive index polymer for ophthalmic applications |
| FR2835828B1 (fr) | 2002-02-08 | 2006-07-14 | Ct De Transfert De Technologie | Procede et composition pour la fabrication de pieces ceramiques par stereo-lithophotographie et application au domaine dentaire |
| FR2835827B1 (fr) | 2002-02-08 | 2004-04-30 | Ct De Transfert De Technologie | Procede et composition pour fabriquer une piece en matiere ceramique par prototypage rapide et pieces obtenues |
| US6833391B1 (en) * | 2003-05-27 | 2004-12-21 | General Electric Company | Curable (meth)acrylate compositions |
| US7271283B2 (en) | 2003-08-29 | 2007-09-18 | General Electric Company | High refractive index, UV-curable monomers and coating compositions prepared therefrom |
| CN101300527B (zh) * | 2005-10-27 | 2011-11-23 | 亨斯迈先进材料（瑞士）有限公司 | 含有包括环丁二醇的聚酯和均质聚酰胺共混物的透明、多层制品的制备 |
| WO2007048819A1 (en) | 2005-10-27 | 2007-05-03 | Huntsman Advanced Materials (Switzerland) Gmbh | Antimony-free photocurable resin composition and three dimensional article |
| DE102005058121B4 (de) | 2005-11-29 | 2007-11-08 | Siemens Ag | Verfahren zum Herstellen keramischer Bauteile, insbesondere elektrisch isolierender Bauteile |
| JP5723283B2 (ja) | 2009-09-30 | 2015-05-27 | 大日本印刷株式会社 | 金属微粒子分散体、導電性基板の製造方法及び導電性基板 |
| KR101311333B1 (ko) * | 2010-06-18 | 2013-10-14 | 주식회사 블루폴리텍 | 자기복원성 자외선 경화형 수지 및 광학필름용 자기복원성 자외선 경화형 수지 조성물 |
| TWI465534B (zh) * | 2010-12-31 | 2014-12-21 | Eternal Materials Co Ltd | 可光固化之黏著組合物 |
| US20130179215A1 (en) | 2012-01-10 | 2013-07-11 | Bank Of America Corporation | Risk assessment of relationships |
| CN102827500B (zh) | 2012-07-16 | 2015-09-16 | 长兴（中国）投资有限公司 | 一种抗刮且耐磨的组合物及其制备方法和应用 |
| AR100394A1 (es) | 2014-05-02 | 2016-10-05 | Dow Global Technologies Llc | Promotores de adhesión de fosfato |
| CA2971877C (en) * | 2015-02-16 | 2019-10-01 | Alcon Inc. | Wet-pack intraocular lens materials with high refractive index |
| JP6475328B2 (ja) | 2015-06-08 | 2019-02-27 | 富士フイルム株式会社 | ３次元印刷用活性光線硬化型インクジェットインクセット、３次元印刷方法、及び、３次元印刷システム |
| JPWO2018051732A1 (ja) | 2016-09-15 | 2019-06-27 | Jnc株式会社 | インク組成物およびこれを用いた有機電界発光素子 |
| JP7203028B2 (ja) * | 2016-12-29 | 2023-01-12 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性高屈折率インク組成物及びインク組成物から調製された物品 |
| CN107383253A (zh) | 2017-06-12 | 2017-11-24 | 西安交通大学 | 一种用于光固化增材制造的生物陶瓷浆料 |
| KR20190001791A (ko) | 2017-06-28 | 2019-01-07 | 주식회사 케이씨씨 | 광경화성 조성물 및 이를 이용하여 제조된 성형품 |
| KR20190001796A (ko) | 2017-06-28 | 2019-01-07 | 주식회사 케이씨씨 | 광경화성 조성물 및 이를 이용하여 제조된 성형품 |
| WO2019023096A1 (en) * | 2017-07-26 | 2019-01-31 | 3M Innovative Properties Company | HIGH-REFRACTIVE INDEX CURABLE INK COMPOSITIONS AND ARTICLES PREPARED THEREFROM INK COMPOSITIONS |
| EP3658352B1 (en) * | 2017-07-28 | 2023-09-27 | Stratasys Ltd. | Additive manufacturing processes employing a material featuring properties of a soft bodily tissue |
| CN107915485A (zh) | 2017-11-28 | 2018-04-17 | 广东工业大学 | 一种压电陶瓷的制备方法 |
| CN107935591B (zh) | 2017-12-01 | 2021-03-23 | 广东工业大学 | 一种改性锆钛酸铅粉体、其制备方法及压电陶瓷成型坯体 |
| CN108218440B (zh) | 2017-12-29 | 2021-10-22 | 深圳长朗智能科技有限公司 | 光固化树脂基陶瓷复合材料及陶瓷胚体脱脂方法 |
| CN108083818B (zh) | 2017-12-29 | 2021-10-22 | 深圳长朗智能科技有限公司 | 结构增强的光固化树脂基陶瓷复合材料及胚体脱脂方法 |
| CN108249930B (zh) * | 2017-12-29 | 2021-10-22 | 深圳长朗智能科技有限公司 | 提供光洁轮廓的光固化树脂基陶瓷复合材料及胚体脱脂方法 |
-
2020
- 2020-09-11 US US17/641,847 patent/US12492275B2/en active Active
- 2020-09-11 EP EP20796917.1A patent/EP4028480A1/en active Pending
- 2020-09-11 KR KR1020227011594A patent/KR20220062041A/ko not_active Withdrawn
- 2020-09-11 WO PCT/IB2020/000754 patent/WO2021048628A1/en not_active Ceased
- 2020-09-11 JP JP2022516133A patent/JP2022548052A/ja active Pending
- 2020-09-11 CN CN202080077309.4A patent/CN114651049A/zh active Pending
- 2020-09-14 TW TW109131569A patent/TWI842949B/zh active
-
2022
- 2022-03-08 IL IL291203A patent/IL291203A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2021048628A5 (https=) | ||
| JP2022548052A (ja) | ３ｄプリンティング用途における使用のための高屈折率モノマーを含有する光硬化性組成物 | |
| JP2008545834A5 (https=) | ||
| JP2004526816A5 (https=) | ||
| JP2016535139A5 (https=) | ||
| JP2002500251A (ja) | 制御されたラジカル重合によるジチオカーバメートからのブロックポリマーの合成方法 | |
| JP2007504284A5 (https=) | ||
| JP2003525286A5 (https=) | ||
| JP2005530888A5 (https=) | ||
| JP2018123332A5 (https=) | ||
| JP2009256201A5 (https=) | ||
| JPWO2022028462A5 (https=) | ||
| JP5076256B2 (ja) | モノマー組成物、それを用いたポリマーおよび眼用レンズ | |
| JPWO2022130990A5 (https=) | ||
| CN107446081A (zh) | 嵌段共聚物的制备方法 | |
| JP2015067795A5 (https=) | ||
| JP5642626B2 (ja) | セラミック押出成形用セラミック混練組成物 | |
| JP2021529174A5 (https=) | ||
| JP2011522087A (ja) | マトリックス材料中におけるナノ粒子の分散のための高効率な分散剤 | |
| TW200902569A (en) | Living radical polymerization reaction promoter | |
| JP6614998B2 (ja) | 歯科用硬化性組成物 | |
| JP2010085647A5 (https=) | ||
| JP2021532183A5 (https=) | ||
| JP2009168963A5 (https=) | ||
| JP5574963B2 (ja) | 歯科用接着性組成物 |