CA3204539A1 - Silicone urethane (meth)acrylates and their use in 3d printing resins and coating compositions - Google Patents

Silicone urethane (meth)acrylates and their use in 3d printing resins and coating compositions Download PDF

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Publication number
CA3204539A1
CA3204539A1 CA3204539A CA3204539A CA3204539A1 CA 3204539 A1 CA3204539 A1 CA 3204539A1 CA 3204539 A CA3204539 A CA 3204539A CA 3204539 A CA3204539 A CA 3204539A CA 3204539 A1 CA3204539 A1 CA 3204539A1
Authority
CA
Canada
Prior art keywords
meth
group
acrylate
independently selected
urethane
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.)
Pending
Application number
CA3204539A
Other languages
English (en)
French (fr)
Inventor
Sadik Amajjahe
Alejandro Jose Benitez Lizardo
David Bleger
Kim Buhning
Maik DIMMERLING
Christian Eger
Frauke Henning
Susann PREUSS
Benjamin Willy
Odo Wunnicke
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.)
Evonik Operations GmbH
Original Assignee
Evonik Operations GmbH
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 Evonik Operations GmbH filed Critical Evonik Operations GmbH
Publication of CA3204539A1 publication Critical patent/CA3204539A1/en
Pending legal-status Critical Current

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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/61—Polysiloxanes
    • 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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • 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
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • 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
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—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
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124—Processes 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
CA3204539A 2021-01-15 2022-01-13 Silicone urethane (meth)acrylates and their use in 3d printing resins and coating compositions Pending CA3204539A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP21151764.4 2021-01-15
EP21151764 2021-01-15
PCT/EP2022/050594 WO2022152775A1 (en) 2021-01-15 2022-01-13 Silicone urethane (meth)acrylates and their use in 3d printing resins and coating compositions

Publications (1)

Publication Number Publication Date
CA3204539A1 true CA3204539A1 (en) 2022-07-21

Family

ID=74184569

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3204539A Pending CA3204539A1 (en) 2021-01-15 2022-01-13 Silicone urethane (meth)acrylates and their use in 3d printing resins and coating compositions

Country Status (7)

Country Link
US (1) US20240101752A1 (https=)
EP (1) EP4277942A1 (https=)
JP (1) JP2024504654A (https=)
KR (1) KR20230129525A (https=)
CN (1) CN116724067A (https=)
CA (1) CA3204539A1 (https=)
WO (1) WO2022152775A1 (https=)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025219995A1 (en) * 2024-04-18 2025-10-23 My Polymers LTD. Photocurable optically clear adhesive formulations
CN118724572B (zh) * 2024-09-03 2024-11-12 中国航发北京航空材料研究院 基于光固化3d打印的硅基陶瓷型芯及其制备方法

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3213058A (en) 1960-12-19 1965-10-19 American Cyanamid Co Polymers reacted with benzotriazole uv absorbers
DE3820294C1 (https=) 1988-06-15 1989-10-05 Th. Goldschmidt Ag, 4300 Essen, De
JP3079117B2 (ja) * 1992-06-18 2000-08-21 ダイセル・ユーシービー株式会社 活性エネルギー線硬化性樹脂組成物
KR100338136B1 (ko) 1998-03-03 2002-05-24 울프 크라스텐센, 스트라쎄 로텐베르그 오르가노폴리실록산 및 오르가노폴리실록산의 제조방법
US6380285B1 (en) 2000-02-01 2002-04-30 Ciba Specialty Chemicals Corporation Bloom-resistant benzotriazole UV absorbers and compositions stabilized therewith
GB2361005B (en) 2000-04-04 2002-08-14 Ciba Sc Holding Ag Synergistic mixtures of uv-absorbers in polyolefins
JP4447310B2 (ja) * 2003-12-26 2010-04-07 三菱化学株式会社 エンボス付き離型紙及びその製造方法
RU2414471C2 (ru) 2005-02-02 2011-03-20 Циба Спешиалти Кемикэлз Холдинг Инк. Бензотриазоловые поглотители уф-лучей со смещенным в длинноволновую область спектром поглощения и их применение
JP2008019402A (ja) * 2006-07-14 2008-01-31 Jsr Corp 硬化性樹脂組成物及び反射防止膜
DE102009028862A1 (de) 2008-12-22 2010-07-01 Evonik Degussa Gmbh Monomerarme 1 : 1 Monoaddukte aus reaktiven olefinischen Verbindungen und Diisocyanaten unter Verwendung einbaubarer Inhibitoren
DE102009002301A1 (de) 2009-04-09 2010-10-14 Evonik Degussa Gmbh Verfahren zur Herstellung von monomerarmen 1:1 Addukten aus Hydroxyalkyl(meth)acrylaten und Diisocyanaten
JP2010265403A (ja) * 2009-05-15 2010-11-25 Hitachi Kasei Polymer Co Ltd 活性エネルギー線硬化性剥離剤組成物及びそれを用いた塗膜形成方法、剥離ライナー
KR101464055B1 (ko) * 2009-12-18 2014-11-20 주고꾸 도료 가부시키가이샤 금속 가교형 오르가노폴리실록산 티오 블록 비닐 공중합체 및 그 금속 가교형 공중합체를 함유하는 방오도료 조성물
EP2875934B1 (de) 2013-11-22 2017-04-05 Technische Universität Wien Vorrichtung zum Verarbeiten von photopolymerisierbarem Material zum schichtweisen Aufbau eines Formkörpers
AT515138B1 (de) 2013-11-22 2016-05-15 Univ Wien Tech Vorrichtung zum Verarbeiten von photopolymerisierbarem Material zum schichtweisen Aufbau eines Formkörpers
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CA2970970C (en) 2014-12-18 2023-01-10 Evonik Degussa Gmbh Radiation-curable coating compounds consisting of a plurality of components, and the use of same in release-coated substrates
JP6519946B2 (ja) * 2015-05-21 2019-05-29 荒川化学工業株式会社 紫外線硬化型コーティング剤組成物及びその硬化膜
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Also Published As

Publication number Publication date
US20240101752A1 (en) 2024-03-28
WO2022152775A1 (en) 2022-07-21
CN116724067A (zh) 2023-09-08
KR20230129525A (ko) 2023-09-08
EP4277942A1 (en) 2023-11-22
JP2024504654A (ja) 2024-02-01

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