KR102513170B1 - 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 - Google Patents

폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 Download PDF

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KR102513170B1
KR102513170B1 KR1020217021144A KR20217021144A KR102513170B1 KR 102513170 B1 KR102513170 B1 KR 102513170B1 KR 1020217021144 A KR1020217021144 A KR 1020217021144A KR 20217021144 A KR20217021144 A KR 20217021144A KR 102513170 B1 KR102513170 B1 KR 102513170B1
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올렉샌더 버토비
웨이 창
리아 랭스돌프
래리 에프. 로데스
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스미토모 베이클리트 컴퍼니 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE 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
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/108—Hydrocarbon resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/13—Morphological aspects
    • C08G2261/135—Cross-linked structures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/144—Side-chains containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/148—Side-chains having aromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/152—Side-groups comprising metal complexes
    • C08G2261/1526—Side-groups comprising metal complexes of Os, Ir, Pt, Ru, Rh or Pd
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/50—Physical properties
    • C08G2261/62—Mechanical aspects
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/70—Post-treatment
    • C08G2261/76—Post-treatment crosslinking

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Polymerization Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
KR1020217021144A 2018-12-21 2019-12-23 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 Active KR102513170B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201862783347P 2018-12-21 2018-12-21
US62/783,347 2018-12-21
US201962830867P 2019-04-08 2019-04-08
US62/830,867 2019-04-08
PCT/US2019/068242 WO2020132665A1 (en) 2018-12-21 2019-12-23 High impact strength 3d printing materials derived from polycycoolefin monomers and crosslinkers

Publications (2)

Publication Number Publication Date
KR20210107033A KR20210107033A (ko) 2021-08-31
KR102513170B1 true KR102513170B1 (ko) 2023-03-24

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US (3) US11142662B2 (https=)
JP (1) JP7223854B2 (https=)
KR (1) KR102513170B1 (https=)
TW (1) TWI801699B (https=)
WO (1) WO2020132665A1 (https=)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102513170B1 (ko) * 2018-12-21 2023-03-24 스미토모 베이클리트 컴퍼니 리미티드 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료
US11286338B2 (en) * 2019-09-18 2022-03-29 Promerus, Llc Two component mass polymerizable compositions containing polycycloolefin monomers and organoruthenium carbide precatalyst
US12435163B2 (en) * 2020-04-01 2025-10-07 3M Innovative Properties Company Compositions comprising romp catalyst and dispersant, cartridges, and methods
KR20230095975A (ko) 2020-10-30 2023-06-29 프로메러스, 엘엘씨 저장수명이 안정적이고 덩이중합이 가능한 개선된 폴리시클로올레핀 조성물
TWI878633B (zh) * 2020-10-30 2025-04-01 日商住友電木股份有限公司 熱特性改良型低損耗膜用聚環烯烴組成物
TWI895585B (zh) 2021-02-02 2025-09-01 日商住友電木股份有限公司 作為光學材料之保存期限長期穩定的光活性本體聚合型多環烯烴組成物
CN116848170A (zh) * 2021-02-02 2023-10-03 普罗米鲁斯有限责任公司 作为光学材料的保存期限长期稳定的光活性本体聚合型多环烯烃组合物
WO2022167944A1 (en) * 2021-02-02 2022-08-11 Apeiron Synthesis S.A. Long shelf life stable organoruthenium complexes as (pre)catalysts for olefin metathesis
US11840586B2 (en) 2021-03-08 2023-12-12 National Technology & Engineering Solutions Of Sandia, Llc Use of latent metathesis polymerization systems for additive manufacturing
KR20240052050A (ko) * 2021-08-31 2024-04-22 메르크 파텐트 게엠베하 조성물
JP2025534788A (ja) * 2022-10-21 2025-10-17 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 組成物
US12586272B2 (en) 2023-06-12 2026-03-24 Ulta Salon, Cosmetics & Fragrance, Inc. Methods and systems for transferring hair characteristics from a reference image to a digital image
US12586157B2 (en) 2023-06-12 2026-03-24 Ulta Salon, Cosmetics & Fragrance, Inc. Methods and systems for modifying hair characteristics in a digital image

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170058145A1 (en) 2015-09-01 2017-03-02 Promerus, Llc Polycycloolefin polymer compositions as optical materials
US20170306171A1 (en) 2014-10-21 2017-10-26 Stratasys Ltd. Three-dimensional inkjet printing using ring-opening metathesis polymerization
US20180194880A1 (en) 2017-01-06 2018-07-12 Promerus, Llc Polycycloolefin polymer compositions as optical materials
US20190039321A1 (en) 2016-02-05 2019-02-07 Stratasys Ltd. Digitally-controlled three-dimensional printing using ring-opening metathesis polymerization

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6838489B2 (en) 2001-03-23 2005-01-04 Cymetech, Llc High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor
AU2003232067A1 (en) * 2002-05-06 2003-11-17 Kerr Corporation Composition curable by metathesis reaction
US7683148B2 (en) * 2003-05-06 2010-03-23 Kerr Corporation Metathesis-curable composition with a reaction control agent
US7875686B2 (en) * 2004-08-18 2011-01-25 Promerus Llc Polycycloolefin polymeric compositions for semiconductor applications
PL400162A1 (pl) 2012-07-27 2014-02-03 Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
KR101572049B1 (ko) * 2012-09-25 2015-11-26 프로메러스, 엘엘씨 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도
JP6258048B2 (ja) * 2014-01-28 2018-01-10 信越化学工業株式会社 有機変性シリコーン樹脂組成物
EP3186319A4 (en) 2014-07-25 2018-04-18 Kateeva, Inc. Organic thin film ink compositions and methods
WO2017068590A1 (en) 2015-10-21 2017-04-27 Stratasys Ltd. Three-dimensional inkjet printing using dicyclopentadiene compounds polymerizable by ring-opening metathesis polymerization
CN108886096B (zh) * 2016-03-22 2022-10-28 普罗米鲁斯有限责任公司 含有双吖丙啶的有机电子组合物和其器件
TWI777027B (zh) * 2018-01-26 2022-09-11 日商住友電木股份有限公司 聚環烯烴單體及由能夠產生光酸作為光學材料的化合物活化之催化劑
TWI794520B (zh) * 2018-06-29 2023-03-01 日商住友電木股份有限公司 作為 3d 列印材料之聚環烯烴單體及由能夠產生光酸之化合物活化之催化劑
KR102513170B1 (ko) * 2018-12-21 2023-03-24 스미토모 베이클리트 컴퍼니 리미티드 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료
US11286338B2 (en) * 2019-09-18 2022-03-29 Promerus, Llc Two component mass polymerizable compositions containing polycycloolefin monomers and organoruthenium carbide precatalyst
TWI834019B (zh) * 2020-01-09 2024-03-01 日商住友電木股份有限公司 作為3d列印材料之穩定本體聚合型多環烯烴組成物及其製備方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170306171A1 (en) 2014-10-21 2017-10-26 Stratasys Ltd. Three-dimensional inkjet printing using ring-opening metathesis polymerization
US20170058145A1 (en) 2015-09-01 2017-03-02 Promerus, Llc Polycycloolefin polymer compositions as optical materials
US20190039321A1 (en) 2016-02-05 2019-02-07 Stratasys Ltd. Digitally-controlled three-dimensional printing using ring-opening metathesis polymerization
US20180194880A1 (en) 2017-01-06 2018-07-12 Promerus, Llc Polycycloolefin polymer compositions as optical materials

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JP2022514616A (ja) 2022-02-14
TW202033682A (zh) 2020-09-16
US20200199391A1 (en) 2020-06-25
JP7223854B2 (ja) 2023-02-16
US20220010157A1 (en) 2022-01-13
US11987716B2 (en) 2024-05-21
US11697744B2 (en) 2023-07-11
US20230295452A1 (en) 2023-09-21
US11142662B2 (en) 2021-10-12
TWI801699B (zh) 2023-05-11
WO2020132665A1 (en) 2020-06-25
KR20210107033A (ko) 2021-08-31

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