JPWO2020016343A5 - - Google Patents
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- JPWO2020016343A5 JPWO2020016343A5 JP2021525371A JP2021525371A JPWO2020016343A5 JP WO2020016343 A5 JPWO2020016343 A5 JP WO2020016343A5 JP 2021525371 A JP2021525371 A JP 2021525371A JP 2021525371 A JP2021525371 A JP 2021525371A JP WO2020016343 A5 JPWO2020016343 A5 JP WO2020016343A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- compound
- item
- 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
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- 239000011342 resin composition Substances 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 33
- 238000007639 printing Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002516 radical scavenger Substances 0.000 claims description 25
- 239000003381 stabilizer Substances 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- -1 propargyl ester Chemical class 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 19
- 150000001345 alkine derivatives Chemical group 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 12
- 239000008139 complexing agent Substances 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 150000003573 thiols Chemical group 0.000 claims description 12
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 11
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005981 pentynyl group Chemical group 0.000 claims description 3
- PVSPTVQNQJFQMP-UHFFFAOYSA-N 1-but-1-ynoxybut-1-yne Chemical compound CCC#COC#CCC PVSPTVQNQJFQMP-UHFFFAOYSA-N 0.000 claims description 2
- LQEOZLPKLZRKTH-UHFFFAOYSA-N 1-pent-1-ynoxypent-1-yne Chemical compound CCCC#COC#CCCC LQEOZLPKLZRKTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 claims description 2
- IXIVHXOMIAKVTE-UHFFFAOYSA-N C(N)(OC#CCCC)=O Chemical compound C(N)(OC#CCCC)=O IXIVHXOMIAKVTE-UHFFFAOYSA-N 0.000 claims description 2
- FIJUUBBOPDVOQZ-UHFFFAOYSA-N CCCC#COC(O)=O Chemical compound CCCC#COC(O)=O FIJUUBBOPDVOQZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011256 inorganic filler Substances 0.000 claims description 2
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 2
- 239000012766 organic filler Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 238000011417 postcuring Methods 0.000 claims description 2
- QVCOXWYMPCBIMH-UHFFFAOYSA-N prop-2-ynyl carbamate Chemical compound NC(=O)OCC#C QVCOXWYMPCBIMH-UHFFFAOYSA-N 0.000 claims description 2
- KTZUEEIBRDOPPX-UHFFFAOYSA-N prop-2-ynyl hydrogen carbonate Chemical compound OC(=O)OCC#C KTZUEEIBRDOPPX-UHFFFAOYSA-N 0.000 claims description 2
- 239000006254 rheological additive Substances 0.000 claims description 2
- 239000012748 slip agent Substances 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 238000010146 3D printing Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000316 bone substitute Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1811896.8A GB2575793A (en) | 2018-07-20 | 2018-07-20 | Resin composition suitable for printing and printing methods |
| GB1811896.8 | 2018-07-20 | ||
| PCT/EP2019/069338 WO2020016343A2 (en) | 2018-07-20 | 2019-07-18 | Resin composition suitable for printing and printing methods |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021532251A JP2021532251A (ja) | 2021-11-25 |
| JPWO2020016343A5 true JPWO2020016343A5 (https=) | 2022-07-25 |
| JP2021532251A5 JP2021532251A5 (https=) | 2022-07-25 |
| JP7440185B2 JP7440185B2 (ja) | 2024-02-28 |
Family
ID=63364393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021525371A Active JP7440185B2 (ja) | 2018-07-20 | 2019-07-18 | 印刷に好適な樹脂組成物および印刷方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US12024580B2 (https=) |
| EP (1) | EP3823810A2 (https=) |
| JP (1) | JP7440185B2 (https=) |
| KR (1) | KR102808043B1 (https=) |
| CN (1) | CN112672873B (https=) |
| AU (1) | AU2019304036B2 (https=) |
| CA (1) | CA3107051A1 (https=) |
| GB (1) | GB2575793A (https=) |
| IL (1) | IL280318B2 (https=) |
| WO (1) | WO2020016343A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3747925A1 (en) * | 2019-06-07 | 2020-12-09 | Henkel AG & Co. KGaA | Radiation-curable composition by anionic polymerization |
| WO2021025686A1 (en) * | 2019-08-06 | 2021-02-11 | Hewlett-Packard Development Company, L.P. | Three-dimensional printing with adhesion promoters |
| JP2022551930A (ja) * | 2019-10-09 | 2022-12-14 | ポリ－メッド インコーポレイテッド | 硬化性ポリマー組成物 |
| WO2022235756A1 (en) * | 2021-05-05 | 2022-11-10 | Trilliant Surgical Llc | Antioxidant polymeric biomaterial for tissue engineering and methods of using same |
| EP4403595A4 (en) * | 2021-09-15 | 2025-08-20 | Namics Corp | RESIN COMPOSITION FOR JET DIFFUSION, ADHESIVE FOR ELECTRONIC COMPONENT, CORRESPONDING CURED PRODUCTS, AND ELECTRONIC COMPONENT |
| KR102447942B1 (ko) * | 2022-04-25 | 2022-09-27 | 주식회사 동우씨제이 | 다이캐스팅 제품에 대한 분체도장 방법 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725228A (en) * | 1971-06-25 | 1973-04-03 | Grace W R & Co | High energy curable liquid polyene polythiol polymer composition |
| JPS556428B2 (https=) * | 1973-05-04 | 1980-02-16 | ||
| DE3837569A1 (de) | 1988-11-04 | 1990-05-10 | Espe Stiftung | Mit sichtbarem licht aushaertbare dentalmassen |
| AU637662B2 (en) * | 1989-12-28 | 1993-06-03 | Hoya Corporation | Polythiol compound, and optical material and product produced therefrom |
| JPH1060114A (ja) * | 1996-05-28 | 1998-03-03 | Loctite Ireland Ltd | 鉄化合物を用いるポリチオールおよびポリエンの貯蔵−安定性の１パーツ系空気活性化される配合組成物 |
| US6045607A (en) | 1999-03-30 | 2000-04-04 | Xerox Corporation | Ink compositions |
| RU2346010C2 (ru) | 2002-12-20 | 2009-02-10 | Эксонмобил Кемикэл Пейтентс Инк. | Способы полимеризации |
| US7425062B2 (en) | 2003-11-12 | 2008-09-16 | E.I. Du Pont De Nemours And Company | Inkjet ink, ink set and method of printing |
| DE602006013855D1 (de) | 2006-12-21 | 2010-06-02 | Agfa Graphics Nv | Tintenstrahldruckverfahren und Tintensätze |
| DE102008013213B3 (de) | 2008-03-07 | 2010-02-18 | Areva Np Gmbh | Verfahren zur katalytischen Rekombination von in einem Gasstrom mitgeführtem Wasserstoff mit Sauerstoff sowie Rekombinationssystem zur Durchführung des Verfahrens |
| EP2278938A4 (en) * | 2008-04-22 | 2013-12-11 | Univ Colorado Regents | THIOL-VINYL AND THIOL-YN SYSTEMS FOR MOLECULE POLYMERS |
| US20100311861A1 (en) * | 2009-06-03 | 2010-12-09 | 3M Innovative Properties Company | Thiol-yne shape memory polymer |
| JP5954789B2 (ja) * | 2009-08-10 | 2016-07-20 | ユーシーエル ビジネス パブリック リミテッド カンパニー | 機能的分子の可逆的共有結合 |
| US20140038826A1 (en) | 2011-01-28 | 2014-02-06 | The Regents Of The University Of Colorado, A Body Corporate | Covalently cross linked hydrogels and methods of making and using same |
| WO2012126695A1 (en) * | 2011-03-23 | 2012-09-27 | Huntsman Advanced Materials (Switzerland) Gmbh | Stable curable thiol-ene composition |
| IN2014DN02047A (https=) * | 2011-10-03 | 2015-05-15 | Synthes Gmbh | |
| EP2604663B1 (en) | 2011-12-16 | 2017-08-09 | Agfa Graphics N.V. | Curable liquids and inkjet inks for food packaging applications |
| TWI593755B (zh) | 2012-10-18 | 2017-08-01 | Mitsubishi Gas Chemical Co | Polymerizable composition and hardened | cured material |
| US20150299412A1 (en) * | 2012-11-02 | 2015-10-22 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Thiol Acrylate Nanocomposite Foams |
| US10144840B2 (en) * | 2013-03-13 | 2018-12-04 | Poly6 Technologies | One-pot, high-performance recycling of polymer waste using renewable polymer synthesis |
| CN105143300B (zh) * | 2013-03-29 | 2017-11-24 | 三井化学株式会社 | 光学材料用聚合性组合物、光学材料及光学材料的制造方法 |
| JP6223127B2 (ja) | 2013-10-30 | 2017-11-01 | 田畑 泰彦 | 歯科用接着性組成物およびキット |
| WO2015067478A1 (de) | 2013-11-05 | 2015-05-14 | Construction Research & Technology Gmbh | Neue bindemittelsysteme |
| WO2015084753A1 (en) | 2013-12-03 | 2015-06-11 | Ocv Interllectual Capital, Llc | Uv-curable glass fiber sizing compositions |
| GB201406683D0 (en) * | 2014-04-14 | 2014-05-28 | Montanuniversitat Leoben | Resin composition suitable for printing and printing method utilizing the same |
| WO2015164524A1 (en) * | 2014-04-22 | 2015-10-29 | Ariste Medical, Inc. | Methods and processes for application of drug delivery polymeric coatings |
| RU2017131285A (ru) * | 2015-02-09 | 2019-03-11 | Мозеик Байосайенсиз, Инк. | Биоразлагаемые тиол-ен-полимеры и способы их получения |
| TWI694125B (zh) | 2015-06-05 | 2020-05-21 | 日商三菱瓦斯化學股份有限公司 | 硬化性組成物及使用其之光學用接著劑 |
| GB201518033D0 (en) * | 2015-10-12 | 2015-11-25 | Montanuniversität Leoben | Printable ester based resin compositions and printing method utilizing the same |
| EP3156463B1 (en) * | 2015-10-13 | 2019-12-18 | Agfa Nv | Uv curable inkjet inks |
| WO2017154428A1 (ja) | 2016-03-07 | 2017-09-14 | 昭和電工株式会社 | 活性エネルギー線硬化性組成物及びその硬化物 |
| JP6782304B2 (ja) * | 2016-04-07 | 2020-11-11 | スリーディー システムズ インコーポレーテッド | ３ｄプリント用のチオール−エンインク |
| ES2957886T3 (es) | 2016-06-20 | 2024-01-29 | Dentsply Sirona Inc | Sistemas y métodos de materiales de fabricación tridimensional para producir productos dentales estratificados |
| BR112019004816A2 (pt) * | 2016-09-12 | 2019-09-03 | Poly6 Tech Inc | método de reciclagem de alto desempenho, de um vaso, para resíduo de polímero usando síntese de polímero renovável |
| EP3797128B1 (en) * | 2018-05-22 | 2023-10-18 | 3M Innovative Properties Company | Process of processing a radiation-curable thiolen based composition with additive-manufacturing technology |
-
2018
- 2018-07-20 GB GB1811896.8A patent/GB2575793A/en not_active Withdrawn
-
2019
- 2019-07-18 WO PCT/EP2019/069338 patent/WO2020016343A2/en not_active Ceased
- 2019-07-18 US US17/260,960 patent/US12024580B2/en active Active
- 2019-07-18 AU AU2019304036A patent/AU2019304036B2/en active Active
- 2019-07-18 EP EP19742350.2A patent/EP3823810A2/en active Pending
- 2019-07-18 CN CN201980058778.9A patent/CN112672873B/zh active Active
- 2019-07-18 CA CA3107051A patent/CA3107051A1/en active Pending
- 2019-07-18 KR KR1020217004557A patent/KR102808043B1/ko active Active
- 2019-07-18 JP JP2021525371A patent/JP7440185B2/ja active Active
- 2019-07-18 IL IL280318A patent/IL280318B2/en unknown
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