JP2018528107A5 - - Google Patents
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- JP2018528107A5 JP2018528107A5 JP2018512552A JP2018512552A JP2018528107A5 JP 2018528107 A5 JP2018528107 A5 JP 2018528107A5 JP 2018512552 A JP2018512552 A JP 2018512552A JP 2018512552 A JP2018512552 A JP 2018512552A JP 2018528107 A5 JP2018528107 A5 JP 2018528107A5
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- weight percent
- temperature
- optionally
- resin
- 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.)
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- 238000000034 method Methods 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 239000003822 epoxy resin Substances 0.000 claims description 21
- 229920000647 polyepoxide Polymers 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 7
- 150000003573 thiols Chemical class 0.000 claims description 7
- 229920001567 vinyl ester resin Polymers 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-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
- -1 alicyclic amine Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000004711 α-olefin Substances 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 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 3
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000004845 glycidylamine epoxy resin Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 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 3
- 239000004843 novolac epoxy resin Substances 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003440 styrenes Chemical class 0.000 claims description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000004848 polyfunctional curative Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562215944P | 2015-09-09 | 2015-09-09 | |
| US62/215,944 | 2015-09-09 | ||
| US201562270637P | 2015-12-22 | 2015-12-22 | |
| US62/270,637 | 2015-12-22 | ||
| US201662369409P | 2016-08-01 | 2016-08-01 | |
| US62/369,409 | 2016-08-01 | ||
| PCT/US2016/050043 WO2017044381A1 (en) | 2015-09-09 | 2016-09-02 | Epoxy dual cure resins for additive manufacturing |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018528107A JP2018528107A (ja) | 2018-09-27 |
| JP2018528107A5 true JP2018528107A5 (enExample) | 2019-10-10 |
| JP6845226B2 JP6845226B2 (ja) | 2021-03-17 |
Family
ID=56940402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018512552A Active JP6845226B2 (ja) | 2015-09-09 | 2016-09-02 | 積層造形用エポキシ二重硬化樹脂 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US10975193B2 (enExample) |
| EP (1) | EP3347399B1 (enExample) |
| JP (1) | JP6845226B2 (enExample) |
| CN (1) | CN108291011B (enExample) |
| WO (1) | WO2017044381A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5986698B1 (ja) | 2015-01-22 | 2016-09-06 | 積水化学工業株式会社 | インクジェット用接着剤、半導体装置の製造方法及び電子部品 |
| US10350823B2 (en) | 2015-12-22 | 2019-07-16 | Carbon, Inc. | Dual precursor resin systems for additive manufacturing with dual cure resins |
| EP3609970A4 (en) * | 2017-04-14 | 2020-11-25 | Polynt Composites USA, Inc. | ADHESIVE COMPOSITION AND PROCESS FOR COATING OBJECTS |
| US11883842B2 (en) | 2017-04-14 | 2024-01-30 | Polynt Composites USA, Inc. | Adhesive compositions and methods for coating objects |
| JP6894015B2 (ja) | 2017-06-21 | 2021-06-23 | カーボン，インコーポレイテッド | 積層造形の方法 |
| EP3705263B1 (en) * | 2017-08-15 | 2024-12-04 | Sumitomo Rubber Industries Ltd. | Rubber composition for shaping three-dimensional laminate |
| CN115179545B (zh) | 2017-12-29 | 2024-12-24 | 斯特拉塔西斯公司 | 用于加成制造的组合物和制品及其使用方法 |
| FR3079517B1 (fr) * | 2018-03-28 | 2021-01-01 | Ecole Centrale Marseille | Procede pour la realisation d’un objet tridimensionnel par un processus de photo-polymerisation multi-photonique et dispositif associe |
| JP7173137B2 (ja) * | 2018-05-23 | 2022-11-16 | コニカミノルタ株式会社 | 立体造形用重合性組成物、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 |
| 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 |
| US11149108B1 (en) | 2018-06-26 | 2021-10-19 | National Technology & Engineering Solutions Of Sandia, Llc | Self-assembly assisted additive manufacturing of thermosets |
| WO2020001835A1 (en) * | 2018-06-26 | 2020-01-02 | Arkema France | Curable compositions based on multistage polymers |
| CN108976777A (zh) * | 2018-07-04 | 2018-12-11 | 宁波市石生科技有限公司 | 一种用于光固化3d打印的柔性材料及其应用 |
| US11292186B2 (en) | 2018-08-01 | 2022-04-05 | Carbon, Inc. | Production of low density products by additive manufacturing |
| US12022642B2 (en) | 2018-08-21 | 2024-06-25 | Laird Technologies, Inc. | Patterned electromagnetic interference (EMI) mitigation materials including carbon nanotubes |
| EP4350442A3 (en) * | 2018-08-21 | 2024-07-03 | Laird Technologies, Inc. | Patterned materials and films and systems and methods for making the same |
| DE102018121067A1 (de) * | 2018-08-29 | 2020-03-05 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Härtbare Zweikomponentenmasse |
| US11407890B2 (en) | 2018-09-10 | 2022-08-09 | Carbon, Inc. | Dual cure additive manufacturing resins for production of flame retardant objects |
| US11426898B2 (en) * | 2018-12-28 | 2022-08-30 | Konica Minolta Business Solutions U.S.A., Inc. | Process for fabrication of fiber composites using dual-cure free-form 3D-printed tailored fiber placement preform |
| JP2020152832A (ja) * | 2019-03-20 | 2020-09-24 | 株式会社リコー | インクジェット用活性エネルギー線硬化型組成物、及び立体物の造形方法 |
| WO2020191690A1 (en) * | 2019-03-28 | 2020-10-01 | Henkel Ag & Co. Kgaa | Photo-curable compositions for additive manufacturing |
| EP3946946A4 (en) * | 2019-03-28 | 2022-08-31 | Henkel AG & Co. KGaA | LIGHT-CURING COMPOSITIONS FOR ADDITIONAL MANUFACTURING |
| DE102019110245A1 (de) * | 2019-04-18 | 2020-10-22 | Comprise Tec Gmbh | Werkstoff, Werkstoffkomposition, Werkstoffherstellungsverfahren und Fertigungsverfahren |
| EP3738771B1 (en) * | 2019-05-13 | 2023-08-16 | Henkel AG & Co. KGaA | Dual cure epoxy formulations for 3d printing applications |
| CN110372997A (zh) * | 2019-07-09 | 2019-10-25 | 捷安特（昆山）有限公司 | 用于制备碳纤维预浸布的环氧树脂组合物及其制备方法 |
| US12360294B2 (en) * | 2019-09-03 | 2025-07-15 | National Research Council Of Canada | 3D printed graded refractive index device |
| JP7776427B2 (ja) * | 2020-02-18 | 2025-11-26 | ローワン・ユニバーシティ | 逐次硬化相互侵入ポリマーによる付加製造高ガラス転移温度材料の網目構造強靭化 |
| WO2021173785A1 (en) * | 2020-02-28 | 2021-09-02 | Carbon, Inc. | One part moisture curable resins for additive manufacturing |
| EP3909748A1 (en) * | 2020-05-12 | 2021-11-17 | TIGER Coatings GmbH & Co. KG | Thermosetting material for use in additive manufacturing |
| CN112057750B (zh) * | 2020-08-06 | 2023-04-07 | 恒新增材制造研究中心(佛山)有限公司 | 一种用于放疗的组织补偿物及其制备方法 |
| WO2022066565A1 (en) * | 2020-09-25 | 2022-03-31 | Carbon, Inc. | Epoxy dual cure resin for the production of moisture-resistant articles by additive manufacturing |
| EP4466142A1 (en) | 2022-01-18 | 2024-11-27 | Noga 3D Innovations Ltd | Dual-cure epoxy resins for 3d printing of high-performance materials |
| WO2023195442A1 (ja) * | 2022-04-04 | 2023-10-12 | 幸士 生田 | 光硬化性組成物、硬化体及び硬化体の製造方法 |
| WO2023220523A1 (en) | 2022-05-09 | 2023-11-16 | Carbon, Inc. | Method for direct coloration of resins for additive manufacturing |
| DE102023120631A1 (de) | 2023-08-03 | 2025-02-06 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Verfahren zum Fügen, Vergießen oder Beschichten von Substraten und härtbare Masse dafür |
| WO2025080931A1 (en) | 2023-10-12 | 2025-04-17 | Carbon, Inc. | Dual cure resins for mixed modulus materials |
| CN118165195B (zh) * | 2024-05-14 | 2024-08-02 | 北京极溯光学科技有限公司 | 双重固化树脂、3d打印方法和3d打印制品 |
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2016
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- 2016-09-02 WO PCT/US2016/050043 patent/WO2017044381A1/en not_active Ceased
- 2016-09-02 EP EP16766749.2A patent/EP3347399B1/en active Active
- 2016-09-02 US US15/754,681 patent/US10975193B2/en active Active
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2021
- 2021-03-04 US US17/192,768 patent/US11814472B2/en active Active
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