CN112335252B - 作为3d打印材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂 - Google Patents

作为3d打印材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂 Download PDF

Info

Publication number
CN112335252B
CN112335252B CN201980043710.3A CN201980043710A CN112335252B CN 112335252 B CN112335252 B CN 112335252B CN 201980043710 A CN201980043710 A CN 201980043710A CN 112335252 B CN112335252 B CN 112335252B
Authority
CN
China
Prior art keywords
group
alkyl
branched
linear
methyl
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
CN201980043710.3A
Other languages
English (en)
Chinese (zh)
Other versions
CN112335252A (zh
Inventor
O·布尔托维
M·L·巴尔考克
张伟
L·F·罗德
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Bakelite Co Ltd
Original Assignee
Sumitomo Bakelite Co Ltd
Promerus LLC
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 Sumitomo Bakelite Co Ltd, Promerus LLC filed Critical Sumitomo Bakelite Co Ltd
Publication of CN112335252A publication Critical patent/CN112335252A/zh
Application granted granted Critical
Publication of CN112335252B publication Critical patent/CN112335252B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • 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
    • B33Y10/00—Processes of additive manufacturing
    • 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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • 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
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring 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)
CN201980043710.3A 2018-06-29 2019-06-28 作为3d打印材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂 Active CN112335252B (zh)

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
CN112335252A CN112335252A (zh) 2021-02-05
CN112335252B true CN112335252B (zh) 2023-07-04

Family

ID=67551408

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201980043710.3A Active CN112335252B (zh) 2018-06-29 2019-06-28 作为3d打印材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂

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
JP5332883B2 (ja) * 2009-04-30 2013-11-06 住友ベークライト株式会社 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
TW201708285A (zh) * 2015-05-06 2017-03-01 普羅梅勒斯有限公司 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
TW201731883A (zh) * 2015-10-01 2017-09-16 普羅梅勒斯有限公司 無氟可光圖案化之含酚官能基之聚合物組成物

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.
US6569373B2 (en) * 2000-03-13 2003-05-27 Object Geometries Ltd. Compositions and methods for use in three dimensional model printing
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
US20050040564A1 (en) * 2003-08-18 2005-02-24 Jones Oliver Systems and methods for using norbornene based curable materials
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
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
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
JP5332883B2 (ja) * 2009-04-30 2013-11-06 住友ベークライト株式会社 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
TW201708285A (zh) * 2015-05-06 2017-03-01 普羅梅勒斯有限公司 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
TW201731883A (zh) * 2015-10-01 2017-09-16 普羅梅勒斯有限公司 無氟可光圖案化之含酚官能基之聚合物組成物

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
WO2020006345A1 (en) 2020-01-02
KR102478771B1 (ko) 2022-12-19
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
CN112335252B (zh) 作为3d打印材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂
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
CN111656792B (zh) 作为光学材料的聚环烯烃单体及由能够产生光酸的化合物活化的催化剂
TWI848199B (zh) 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
US11286338B2 (en) Two component mass polymerizable compositions containing polycycloolefin monomers and organoruthenium carbide precatalyst
TWI834019B (zh) 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
US11834542B2 (en) Single component mass polymerizable compositions containing polycycloolefin monomers and organoruthenium carbide precatalyst
CN114901712A (zh) 作为光学材料的Pd（AcAc）2L催化多环烯烃组合物的UV活性衍生物
CN114144450A (zh) 作为光学材料的稳定的聚环烯烃聚合物及无机纳米组合物
CN116457380A (zh) 储存寿命稳定且可本体聚合的改良型多环烯烃组合物

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
TA01 Transfer of patent application right
TA01 Transfer of patent application right

Effective date of registration: 20230608

Address after: Tokyo, Japan

Applicant after: SUMITOMO BAKELITE Co.,Ltd.

Address before: Ohio, USA

Applicant before: PROMERUS, LLC

GR01 Patent grant
GR01 Patent grant