KR102478771B1 - 3d 프린팅 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매 - Google Patents

3d 프린팅 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매 Download PDF

Info

Publication number
KR102478771B1
KR102478771B1 KR1020217001421A KR20217001421A KR102478771B1 KR 102478771 B1 KR102478771 B1 KR 102478771B1 KR 1020217001421 A KR1020217001421 A KR 1020217001421A KR 20217001421 A KR20217001421 A KR 20217001421A KR 102478771 B1 KR102478771 B1 KR 102478771B1
Authority
KR
South Korea
Prior art keywords
alkyl
aryl
formula
methyl
hept
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.)
Active
Application number
KR1020217001421A
Other languages
English (en)
Korean (ko)
Other versions
KR20210028196A (ko
Inventor
올레크산드르 부토비이
매튜 엘. 바르쵸크
웨이 장
래리 에프. 로도스
Original Assignee
스미토모 베이클리트 컴퍼니 리미티드
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 스미토모 베이클리트 컴퍼니 리미티드 filed Critical 스미토모 베이클리트 컴퍼니 리미티드
Publication of KR20210028196A publication Critical patent/KR20210028196A/ko
Application granted granted Critical
Publication of KR102478771B1 publication Critical patent/KR102478771B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • 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
    • C08G61/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06Macromolecular 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
    • C08G61/08Macromolecular 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2265Carbenes or carbynes, i.e.(image)
    • B01J31/2278Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE 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
    • B33Y70/00Materials specially adapted for additive manufacturing
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/10Printing inks based on artificial resins
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/821Ruthenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215Sulfur-containing compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0244Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE 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
    • B33Y10/00Processes of 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
    • C08G2261/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325Monomer 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
    • 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
    • C08G2261/00Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40Polymerisation processes
    • C08G2261/41Organometallic coupling reactions
    • C08G2261/418Ring opening metathesis polymerisation [ROMP]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Manufacturing & Machinery (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
KR1020217001421A 2018-06-29 2019-06-28 3d 프린팅 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매 Active KR102478771B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201862691833P 2018-06-29 2018-06-29
US62/691,833 2018-06-29
US201962798047P 2019-01-29 2019-01-29
US62/798,047 2019-01-29
US201962831250P 2019-04-09 2019-04-09
US62/831,250 2019-04-09
PCT/US2019/039712 WO2020006345A1 (en) 2018-06-29 2019-06-28 Polycycloolefin monomers and catalyst activated by compound capable of generating photoacid as 3d printing materials

Publications (2)

Publication Number Publication Date
KR20210028196A KR20210028196A (ko) 2021-03-11
KR102478771B1 true KR102478771B1 (ko) 2022-12-19

Family

ID=67551408

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020217001421A Active KR102478771B1 (ko) 2018-06-29 2019-06-28 3d 프린팅 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매

Country Status (6)

Country Link
US (1) US11230624B2 (https=)
JP (1) JP7456950B2 (https=)
KR (1) KR102478771B1 (https=)
CN (1) CN112335252B (https=)
TW (1) TWI794520B (https=)
WO (1) WO2020006345A1 (https=)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11939410B2 (en) * 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
KR102513170B1 (ko) 2018-12-21 2023-03-24 스미토모 베이클리트 컴퍼니 리미티드 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료
WO2021072206A1 (en) 2019-10-10 2021-04-15 PolySpectra, Inc. Olefin metathesis photopolymers
TWI848199B (zh) * 2020-01-02 2024-07-11 日商住友電木股份有限公司 作為光學材料之保存期限延長的本體聚合型多環烯烴組成物
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
US20230078824A1 (en) * 2020-02-28 2023-03-16 Carbon, Inc. Methods of making a three-dimensional object
US12435163B2 (en) * 2020-04-01 2025-10-07 3M Innovative Properties Company Compositions comprising romp catalyst and dispersant, cartridges, and methods
JP7762668B2 (ja) 2020-06-10 2025-10-30 インクビット, エルエルシー 光開始カチオン開環重合用材料及びその用途
EP4225824A4 (en) * 2020-10-09 2024-10-30 Polyspectra, Inc. ORAL PRODUCTS AND THEIR PRODUCTION PROCESSES
US11718710B2 (en) * 2020-10-14 2023-08-08 The Board Of Trustees Of The University Of Illinois Method of light-promoted frontal ring-opening metathesis polymerization
WO2022167944A1 (en) * 2021-02-02 2022-08-11 Apeiron Synthesis S.A. Long shelf life stable organoruthenium complexes as (pre)catalysts for olefin metathesis
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
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
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
WO2025012183A1 (en) 2023-07-10 2025-01-16 Merck Patent Gmbh Composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020008333A1 (en) 2000-03-13 2002-01-24 Eduardo Napadensky Compositions and methods for use in three dimensional model printing
US20050040564A1 (en) 2003-08-18 2005-02-24 Jones Oliver Systems and methods for using norbornene based curable materials
JP2010260916A (ja) 2009-04-30 2010-11-18 Sumitomo Bakelite Co Ltd 感光性組成物、光導波路、光配線、光電気混載基板、電子機器、および光導波路の形成方法
WO2016063282A1 (en) 2014-10-21 2016-04-28 Stratasys Ltd. Three-dimensional inkjet printing using ring-opening metathesis polymerization

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE902790A (fr) * 1984-07-12 1986-01-02 Sandoz Sa Procede de preparation de xanthones et de thioxanthones.
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
CN100484755C (zh) 2003-06-27 2009-05-06 日本瑞翁株式会社 叠层体及其制造方法
DE102009013710A1 (de) * 2009-03-20 2010-09-23 Merck Patent Gmbh Polymere aus Mischungen mit Vinylether-Monomeren
KR101842735B1 (ko) * 2010-09-02 2018-03-27 메르크 파텐트 게엠베하 전자 디바이스용 게이트 절연체 층
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
EP3186319A4 (en) 2014-07-25 2018-04-18 Kateeva, Inc. Organic thin film ink compositions and methods
TWI659046B (zh) * 2015-05-06 2019-05-11 Sumitomo Bakelite Co., Ltd. 作爲永久介電材料的順丁烯二醯亞胺及環烯烴單體之聚合物
TWI675059B (zh) 2015-09-01 2019-10-21 日商住友電木股份有限公司 作爲光學材料的聚環烯烴聚合物組成物
US10054854B2 (en) * 2015-10-01 2018-08-21 Promerus, Llc Fluorine free photopatternable phenol functional group containing polymer compositions
WO2017068590A1 (en) 2015-10-21 2017-04-27 Stratasys Ltd. Three-dimensional inkjet printing using dicyclopentadiene compounds polymerizable by ring-opening metathesis polymerization
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020008333A1 (en) 2000-03-13 2002-01-24 Eduardo Napadensky Compositions and methods for use in three dimensional model printing
US20050040564A1 (en) 2003-08-18 2005-02-24 Jones Oliver Systems and methods for using norbornene based curable materials
JP2010260916A (ja) 2009-04-30 2010-11-18 Sumitomo Bakelite Co Ltd 感光性組成物、光導波路、光配線、光電気混載基板、電子機器、および光導波路の形成方法
WO2016063282A1 (en) 2014-10-21 2016-04-28 Stratasys Ltd. Three-dimensional inkjet printing using ring-opening metathesis polymerization

Also Published As

Publication number Publication date
CN112335252A (zh) 2021-02-05
JP7456950B2 (ja) 2024-03-27
JP2021529855A (ja) 2021-11-04
KR20210028196A (ko) 2021-03-11
CN112335252B (zh) 2023-07-04
WO2020006345A1 (en) 2020-01-02
US11230624B2 (en) 2022-01-25
US20200002466A1 (en) 2020-01-02
TW202000722A (zh) 2020-01-01
TWI794520B (zh) 2023-03-01

Similar Documents

Publication Publication Date Title
KR102478771B1 (ko) 3d 프린팅 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매
JP7223854B2 (ja) ポリシクロオレフィンモノマー及び架橋剤に由来する高衝撃強度の3d印刷材料
KR102226642B1 (ko) 광학 재료로서의 폴리시클로올레핀 단량체 및 광산발생화합물에 의해 활성화하는 촉매
KR102478775B1 (ko) 저장 수명을 향상한 광학재료로서의 덩이중합성 폴리시클로올레핀 조성물
KR102478768B1 (ko) 3d 프린팅 재료로서의 안정적 덩이중합성 폴리시클로올레핀 조성물 및 그 제조방법
KR20200040779A (ko) 광학재료로서의 폴리시클로올레핀 중합체 및 무기 나노입자 조성물
US11834542B2 (en) Single component mass polymerizable compositions containing polycycloolefin monomers and organoruthenium carbide precatalyst
KR102814148B1 (ko) 광학재료로서의 안정적인 폴리시클로올레핀 중합체 및 무기 나노입자 조성물

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20210115

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20220627

Comment text: Request for Examination of Application

PA0302 Request for accelerated examination

Patent event date: 20220627

Patent event code: PA03022R01D

Comment text: Request for Accelerated Examination

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20221109

N231 Notification of change of applicant
PN2301 Change of applicant

Patent event date: 20221202

Comment text: Notification of Change of Applicant

Patent event code: PN23011R01D

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20221214

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20221215

End annual number: 3

Start annual number: 1

PG1601 Publication of registration