CN108350145B - 用于增材制造的氰酸酯双重固化树脂 - Google Patents

用于增材制造的氰酸酯双重固化树脂 Download PDF

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CN108350145B
CN108350145B CN201680051002.0A CN201680051002A CN108350145B CN 108350145 B CN108350145 B CN 108350145B CN 201680051002 A CN201680051002 A CN 201680051002A CN 108350145 B CN108350145 B CN 108350145B
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cyanatophenyl
phenyl
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CN108350145A (zh
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M.S.梅尼奥
J.P.罗兰
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Carbon Inc
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Carbon Inc
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065Preparatory processes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/20Apparatus for additive manufacturing; Details thereof or accessories therefor
    • B29C64/264Arrangements for irradiation
    • B29C64/277Arrangements for irradiation using multiple radiation means, e.g. micromirrors or multiple light-emitting diodes [LED]
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/02Thermal after-treatment
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/04After-treatment of articles without altering their shape; Apparatus therefor by wave energy or particle radiation, e.g. for curing or vulcanising preformed articles
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y10/00Processes of additive manufacturing
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00Materials specially adapted for additive manufacturing
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065Preparatory processes
    • C08G73/0655Preparatory processes from polycyanurates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065Preparatory processes
    • C08G73/0655Preparatory processes from polycyanurates
    • C08G73/0661Preparatory processes from polycyanurates characterised by the catalyst used
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C08L61/14Modified phenol-aldehyde condensates
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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    • B29C35/00Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
    • B29C35/08Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • B29C2035/0833Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using actinic light
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
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    • B29C35/08Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • B29C2035/0855Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using microwave
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/02Thermal after-treatment
    • B29C2071/022Annealing
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C35/00Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
    • B29C35/02Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
    • B29C35/08Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
    • B29C35/0805Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2039/00Use of polymers with unsaturated aliphatic radicals and with a nitrogen or a heterocyclic ring containing nitrogen in a side chain or derivatives thereof as moulding material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2079/00Use of polymers having nitrogen, with or without oxygen or carbon only, in the main chain, not provided for in groups B29K2061/00 - B29K2077/00, as moulding material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00Materials specially adapted for additive manufacturing
    • B33Y70/10Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials

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  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • Optics & Photonics (AREA)
  • Toxicology (AREA)
  • Thermal Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Polymerisation Methods In General (AREA)
  • General Chemical & Material Sciences (AREA)
CN201680051002.0A 2015-09-04 2016-09-02 用于增材制造的氰酸酯双重固化树脂 Active CN108350145B (zh)

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US201562214601P 2015-09-04 2015-09-04
US62/214601 2015-09-04
US201562270635P 2015-12-22 2015-12-22
US62/270635 2015-12-22
PCT/US2016/050035 WO2017040883A1 (en) 2015-09-04 2016-09-02 Cyanate ester dual cure resins for additive manufacturing

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CN108350145A CN108350145A (zh) 2018-07-31
CN108350145B true CN108350145B (zh) 2021-06-22

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EP (1) EP3344676B1 (enExample)
JP (1) JP7069006B2 (enExample)
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WO (1) WO2017040883A1 (enExample)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
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
WO2018182974A1 (en) * 2017-03-27 2018-10-04 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
JP7163956B2 (ja) * 2018-04-02 2022-11-01 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
CN112384188A (zh) 2018-06-29 2021-02-19 3M创新有限公司 使用聚碳酸酯二醇制备的正畸制品、可聚合组合物以及制备制品的方法
WO2020055682A1 (en) 2018-09-10 2020-03-19 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
JP7491910B2 (ja) * 2018-09-28 2024-05-28 ストラタシス リミテッド 熱的に安定な物体の三次元インクジェット印刷
IL281855B (en) 2018-09-28 2022-07-01 Stratasys Ltd Additive manufacturing process with partial fusion
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
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
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
US11637377B2 (en) 2018-12-04 2023-04-25 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
JP7520051B2 (ja) 2019-05-30 2024-07-22 ロジャーズ・コーポレイション ステレオリソグラフィ用光硬化性組成物、その組成物を使用するステレオリソグラフィ法、そのステレオリソグラフィ法によって形成されたポリマーコンポーネント、及びそのポリマーコンポーネントを含むデバイス
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
EP4045291A4 (en) * 2019-10-17 2023-11-15 Henkel AG & Co. KGaA METHOD FOR PRODUCING THREE-DIMENSIONAL PARTS WITH SUPERIOR PROPERTIES
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
US11352514B1 (en) 2021-06-09 2022-06-07 Altana New Technologies Gmbh Dual-curable inkjet composition
ES2946436T3 (es) * 2021-06-09 2023-07-18 Altana New Tech Gmbh Composición para inyección de tinta de éster de cianato de curado dual
WO2023139578A1 (en) 2022-01-18 2023-07-27 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
WO2023247374A1 (de) 2022-06-23 2023-12-28 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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0945744A2 (en) * 1998-03-26 1999-09-29 Hughes Electronics Corporation Front end preparation procedure for coupling of light into a multi-mode fiber
CN103080252A (zh) * 2010-09-07 2013-05-01 3M创新有限公司 可固化树脂组合物和使用它制造的多层层合物
WO2015200173A1 (en) * 2014-06-23 2015-12-30 Carbon3D, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening

Family Cites Families (102)

* Cited by examiner, † Cited by third party
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
US4757132A (en) 1986-10-20 1988-07-12 General Electric Company Cyclic polyester oligomer polymerization
US4775741A (en) 1986-07-21 1988-10-04 General Electric Company Preparation of resin composition from cyclic polycarbonate oligomers from spirobiindane bisphenol
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
DE69315003T2 (de) 1992-07-17 1998-03-12 Ethicon Inc Strahlenhärtbare Urethan-Acrylatprepolymere und vernetzte Polymere
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
DE59407524D1 (de) 1993-08-26 1999-02-04 Ciba Geigy 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
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
WO2001059524A1 (en) * 2000-02-08 2001-08-16 Vantico Ag Liquid, radiation-curable composition, especially for stereolithography
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
EP1632533B1 (en) 2003-06-09 2013-04-10 Kaneka Corporation Process for producing modified epoxy resin
CN100581792C (zh) 2004-03-22 2010-01-20 亨斯迈先进材料(瑞士)有限公司 可光致固化组合物
US7642316B2 (en) 2004-10-14 2010-01-05 Dow Global Technologies, Inc. Rubber modified monovinylidene aromatic polymers and fabricated articles prepared therefrom
EP1810206B1 (en) 2004-10-19 2014-07-09 Rolls-Royce Corporation Method associated with anisotropic shrink in sintered ceramic items
WO2006052726A1 (en) 2004-11-10 2006-05-18 Dow Global Technologies, Inc. Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom
CA2626327C (en) * 2005-10-27 2014-12-16 Huntsman Advanced Materials (Switzerland) Gmbh Antimony-free photocurable resin composition and three dimensional article
US20070178133A1 (en) 2005-11-09 2007-08-02 Liquidia Technologies, Inc. Medical device, materials, and methods
US8092465B2 (en) 2006-06-09 2012-01-10 Biomet Manufacturing Corp. Patient specific knee alignment guide and associated method
US8591516B2 (en) 2006-02-27 2013-11-26 Biomet Manufacturing, Llc Patient-specific orthopedic instruments
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
US20100227941A1 (en) 2007-03-20 2010-09-09 Dsm Ip Assets B.V. Stereolithography resin compositions and three-dimensional objects made therefrom
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
ATE524765T1 (de) 2007-04-03 2011-09-15 Basf Se Fotoaktivierbare stickstoffbasen
US8088245B2 (en) 2007-04-11 2012-01-03 Dow Global Technologies Llc Structural epoxy resins containing core-shell rubbers
CN101679579B (zh) 2007-06-20 2012-05-30 陶氏环球技术公司 对温度变化的敏感性非常低的耐碰撞环氧粘合剂
DK2052693T4 (da) 2007-10-26 2021-03-15 Envisiontec Gmbh Proces og fri-formfabrikationssystem til at fremstille en tredimensionel genstand
US20100280151A1 (en) 2009-05-04 2010-11-04 Toray Industries, Inc. Toughened fiber reinforced polymer composite with core-shell particles
US9839434B2 (en) 2009-10-29 2017-12-12 Zimmer, Inc. Patient-specific mill guide
WO2011075555A1 (en) 2009-12-17 2011-06-23 Dsm Ip Assets, B.V. Led curable liquid resin compositions for additive fabrication
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
WO2012106256A1 (en) 2011-01-31 2012-08-09 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
CN104011163A (zh) 2011-12-12 2014-08-27 株式会社Lg化学 用于制造电路板的氰酸酯树脂组合物以及含有其的柔性覆金属层压制品
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
WO2014015432A1 (en) 2012-07-23 2014-01-30 Orthosoft Inc. Patient-specific instrumentation for implant revision surgery
BR112014032019A2 (pt) 2012-08-27 2017-06-27 Dow Global Technologies Llc adesivo, método para fazer um adesivo de epóxi e kit
EP2895564A2 (en) 2012-09-17 2015-07-22 3M Innovative Properties Company Powder coating epoxy compositions, methods, and articles
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.
EP2956821B8 (en) * 2013-02-12 2018-06-27 Carbon, Inc. Method and apparatus for three-dimensional fabrication
CA2898106A1 (en) 2013-02-12 2014-08-21 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
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
EP3253558B1 (en) * 2015-02-05 2020-04-08 Carbon, 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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0945744A2 (en) * 1998-03-26 1999-09-29 Hughes Electronics Corporation Front end preparation procedure for coupling of light into a multi-mode fiber
CN103080252A (zh) * 2010-09-07 2013-05-01 3M创新有限公司 可固化树脂组合物和使用它制造的多层层合物
WO2015200173A1 (en) * 2014-06-23 2015-12-30 Carbon3D, Inc. Methods of producing three-dimensional objects from materials having multiple mechanisms of hardening

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