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WO2016134972A1 - Mélange de silicone contenant des acrylates pour jet d'encre et distributeur d'impression 3d - Google Patents

Mélange de silicone contenant des acrylates pour jet d'encre et distributeur d'impression 3d Download PDF

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Publication number
WO2016134972A1
WO2016134972A1 PCT/EP2016/052826 EP2016052826W WO2016134972A1 WO 2016134972 A1 WO2016134972 A1 WO 2016134972A1 EP 2016052826 W EP2016052826 W EP 2016052826W WO 2016134972 A1 WO2016134972 A1 WO 2016134972A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
printed
printer
radiation
polysiloxane
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.)
Ceased
Application number
PCT/EP2016/052826
Other languages
English (en)
Inventor
Johan Lub
Rifat Ata Mustafa Hikmet
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.)
Signify Holding BV
Original Assignee
Philips Lighting Holding BV
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 Philips Lighting Holding BV filed Critical Philips Lighting Holding BV
Publication of WO2016134972A1 publication Critical patent/WO2016134972A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE 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
    • B33Y10/00—Processes of additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE 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
    • B33Y70/00—Materials specially adapted for additive manufacturing

Definitions

  • 3D inkjet printing and 3D dispension are additive manufacturing technologies used for modeling, prototyping, and production applications. These technologies work on an "additive" principle by laying down a liquid in the forms of drops or by a continuous flow, respectively, of a polymerizable liquid which is photopolymerized on "the flow”.
  • acrylates By using for example acrylates, polymerization (see scheme below, wherein photo- polymerization of silicone acrylates is shown, in correspondence with the invention) can be fast enough to obtain the 3D structure.
  • the use of these pure acrylates is - however - not desired as they do not show the high stability of silicones.
  • These polymerized siloxanes or polysiloxanes materials consist of an inorganic silicon-oxygen backbone ( •• -Si-O-Si-O-Si- ⁇ - ⁇ ⁇ ) with organic side groups attached to the silicon atoms, which are four-coordinate.
  • R side groups may in principle be different, instead of the formula [(R 2 )SiO] n also the formula [(Rl ,R2)SiO] n (not taking into account the terminal groups), might be applied.
  • R1,R2 does not exclude that different Si backbone elements may comprise the same side groups, but also more than two different types of side groups may be comprised by the silicone.
  • Ri being the polysiloxane
  • R 2 , R 3 , R 4 , R 5 , and Re independently being selected from for instance the group consisting of H, an alkyl, an alkenyl, an alkynyl, an ether, an ester, a polysiloxane, etc., with especially at least one R 2 , R 3 , R4, R 5 , and 5, and even more especially only one, being a polysiloxane.
  • R 2 , R 3 , R4, R5, and 5 will comprise (another) polysiloxane molecule, covalently linked to the RI polysiloxane molecule via the acrylate-based cross-link.
  • C 4 indicates the carbon atom to which OORi, C 3 and C 2 are covalently bound (i.e. in the case of methacrylic acid, the carbon atom to which COOH, CH 3 and CH 2 are covalently bound).
  • substantially any group or groups (including H) may be associated via the acrylate group to the polysiloxanes.
  • R 1 -R6 may differ from application to application.
  • the weight percentage of C 2 +C 3 +Ci + C 4 + 2*0 +6H is evaluated, relative to the total weight of the composition.
  • the thus obtained 3D printed object comprises a printed composition of polymerized siloxanes especially comprising in the range of 0.5-8 wt.%, more especially in the range of 1-5 wt.% acrylate groups, wherein the weight of the acrylate groups is defined as the weight of methacrylic acid.
  • acrylate groups especially refer to the acrylate groups comprised by the acrylate-based cross-links (between the polysiloxanes).
  • the total weight of the composition relates to weight of the (cross-linked and/or cured) polysiloxanes.
  • the composition may further include material not covalently linked to the polysiloxanes. Such material is not included in the total weight of the composition for the purpose of determining the acrylate groups. Examples of such materials may include one or more of a filler material, a preservative, a stabilizer, a pigment, a luminescent material, a catalyst, etc..
  • the composition may further comprise a photo polymerization catalyst, such as irgacure, and the method may further comprise photo polymerizing the printed composition to provide said 3D printed object.
  • a photo polymerization catalyst such as irgacure
  • the method may further comprise photo polymerizing the printed composition to provide said 3D printed object.
  • visible light or other radiation may be used to start and/or speed up the cross-linking.
  • the 3D printer may further comprise a radiation source configured to irradiate with radiation said printed composition, wherein the radiation is selected from the group consisting of UV radiation, visible radiation, and IR radiation, especially at least UV radiation.
  • the composition comprises (meth)acryloxypropyl terminated poly(dimethyl) siloxanes and one or more of (a) poly(dimethylsiloxane-co- methylhydrosiloxanes and vinyl terminated poly(dimethyl siloxanes), and (b)
  • radiation may be applied to cross-link the siloxanes via the acrylate groups, and e.g. heat may be used to (further) cure the composition by poly silo xane curing (as known in the art).
  • the former bonding is herein indicated as “acrylate-based cross-link” and the latter is herein indicated as “siloxanes crosslink”.
  • the method comprises 3D printing said composition to provide said printed composition, wherein during or after or during and after printing the composition downstream from a printer nozzle of the 3D printer is irradiated with radiation and subjected to heat.
  • a 3D printer may especially be applied to execute the herein described method.
  • the invention provides a 3D printer comprising a printer head for printing a composition comprising polymerizable compounds to a receiver item, the 3D printer further optionally comprising (i) a heating unit configured to heat said printed composition, and (ii) a radiation source configured to irradiate with radiation said printed composition, wherein the radiation is selected from the group consisting of UV radiation, visible radiation, and IR radiation, the 3D printer further comprising a control unit configured to control the printer head, the heating unit and the radiation source.
  • the heating unit and the radiation source are different items, i.e. the source of radiation is not especially designed to provide the heat the printed composition.
  • the source of radiation may also be used for this purpose.
  • the radiation source comprises a laser, especially a UV laser.
  • Such source may be used to locally irradiate the printed composition.
  • the term "UV laser” also relates to a source of radiation including a laser and providing UV radiation (e.g. by frequency doubling, etc.).
  • the heating unit may optionally comprise an IR laser.
  • Such laser may be used to locally heat the (just) deposited polymerizable polysiloxane material.
  • the 3D printer may amongst others be configured as inkjet 3D printer or as dispenser 3D printer.
  • the invention provides such a mixture where the photopolymerisable system consist of a mixture of methacryloxypropyl terminated poly(dimethylsiloxane) and a photo initiator.
  • the invention also provides 3-D produced structures using the mixtures.
  • the invention may amongst others be applied in 3D inkjet printers and dispensers to enable 3D printing of transparent or coloured or scattering parts.
  • 3D printed object refers to a three dimensional object obtained via 3D printing (which is an additive manufacturing process).
  • FIGs. 2a-2e schematically depict some aspects of the invention
  • Fig. 1 schematically depicts an embodiment of a 3D printer.
  • Reference 500 indicates this 3D printer.
  • Reference 530 indicates the functional unit configured to 3D print, especially FDM 3D printing; this reference may also indicate the 3D printing stage unit.
  • the printer head for providing 3D printed material such as a FDM 3D printer head is schematically depicted.
  • Reference 501 indicates the printer head.
  • the 3D printer of the present invention may especially include a plurality of printer heads, though other
  • Reference 502 indicates a printer nozzle.
  • the 3D printer of the present invention may especially include a plurality of printer nozzles, though other embodiments are also possible.
  • Reference 320 indicates a filament of printable 3D printable material (such as indicated above). For the sake of clarity, not all features of the 3D printer have been depicted, only those that are of especial relevance for the present invention.
  • the 3D printer 500 is configured to generate a 3D item 100 by depositing on a receiver item 550 a plurality of filaments 320 wherein each filament 20 comprises 3D printable material,.
  • the 3D printer 500 is configured to heat the filament material upstream of the printer nozzle 502. This may e.g.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • Optics & Photonics (AREA)

Abstract

L'invention concerne un procédé de fabrication d'un objet (100) imprimé en 3D comprenant une impression 3D faisant intervenir une imprimante 3D (500), une composition (200) contenant des composés polymérisables (210) pour produire une composition imprimée (201), les composés polymérisables (210) contenant des polysiloxanes (220) contenant des groupes acrylate (225) polymérisables liés de manière covalente audits polysiloxanes (220), et la polymérisation d'au moins une partie du nombre total de groupes acrylate (225) de la composition imprimée (201) pour produire ledit objet (100) imprimé en 3D doté de polysiloxanes polymérisés (230).
PCT/EP2016/052826 2015-02-23 2016-02-10 Mélange de silicone contenant des acrylates pour jet d'encre et distributeur d'impression 3d Ceased WO2016134972A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP15156100 2015-02-23
EP15156100.8 2015-02-23

Publications (1)

Publication Number Publication Date
WO2016134972A1 true WO2016134972A1 (fr) 2016-09-01

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Country Status (1)

Country Link
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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107298860A (zh) * 2016-09-12 2017-10-27 宁波创导三维医疗科技有限公司 一种硅胶3d打印机及其打印方法
WO2018151850A1 (fr) * 2017-02-16 2018-08-23 Arizona Board Of Regents On Behalf Of The University Of Arizona Fabrication additive assistée par laser d'optiques utilisant des matériaux thermiquement durcissables
WO2018234643A1 (fr) 2017-06-22 2018-12-27 Elkem Silicones France Sas Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones
WO2019102695A1 (fr) * 2017-11-22 2019-05-31 マクセルホールディングス株式会社 Composition pour matériau de modèle
WO2020016282A1 (fr) * 2018-07-20 2020-01-23 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Fabrication de corps moulés à partir d'un polymère hybride inorganique-organique à haute résolution par impression 3d, corps moulés à résistances élevées à la flexion et à modules d'élasticité élevés ainsi que leur utilisation à des fins dentaires
WO2020059650A1 (fr) * 2018-09-20 2020-03-26 信越化学工業株式会社 Composition de silicone durcissable par rayonnement uv et son produit durci
WO2020080011A1 (fr) * 2018-10-19 2020-04-23 信越化学工業株式会社 Composition de silicone durcissable aux uv et produit durci associé
CN111417672A (zh) * 2017-09-26 2020-07-14 美国圣戈班性能塑料公司 可光致固化组合物及将其用于进行3d打印的方法
US11104802B2 (en) 2016-09-26 2021-08-31 University Of Washington PDMS resin for stereolithographic 3D-printing of PDMS
CN113811436A (zh) * 2019-05-13 2021-12-17 汉高股份有限及两合公司 可辐射固化且可印刷的聚硅氧烷组合物
EP3981578A1 (fr) * 2020-10-06 2022-04-13 Sumitomo Rubber Industries, Ltd. Composition de polymère pour stéréolithographie
WO2022240955A1 (fr) 2021-05-12 2022-11-17 Elkem Silicones USA Corp. Procédé de production d'un article imprimé tridimensionnel
WO2022240961A1 (fr) 2021-05-12 2022-11-17 Elkem Silicones USA Corp. Procédé de production d'un article imprimé tridimensionnel
US11945935B2 (en) 2019-05-08 2024-04-02 Saint-Gobain Performance Plastics Corporation Hydrophilic polymer compositions
US11944553B2 (en) 2021-01-08 2024-04-02 DePuy Synthes Products, Inc. Expanding spinal fusion cage
EP4344873A1 (fr) 2022-09-27 2024-04-03 Elkem Silicones France SAS Post-traitement d'un article en silicone élastomère imprimé en 3d
US11958240B2 (en) 2019-08-08 2024-04-16 Hewlett-Packard Development Company, L.P. Three-dimensional printing with organosilanes
US11976172B2 (en) 2019-04-16 2024-05-07 Saint-Gobain Performance Plastics Corporation Dual cure compositions

Citations (2)

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WO2003037606A1 (fr) * 2001-10-26 2003-05-08 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. Procede pour creer des corps tridimensionnels ou des surfaces tridimensionnelles par rayonnement laser
WO2014108364A1 (fr) 2013-01-10 2014-07-17 Luxexcel Holding B.V. Procédé d'impression d'un élément optique

Patent Citations (2)

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WO2003037606A1 (fr) * 2001-10-26 2003-05-08 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. Procede pour creer des corps tridimensionnels ou des surfaces tridimensionnelles par rayonnement laser
WO2014108364A1 (fr) 2013-01-10 2014-07-17 Luxexcel Holding B.V. Procédé d'impression d'un élément optique

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JOSEF KUMPFMUELLER ET AL: "Two-photon-induced Microfabrication of Flexible Optical Waveguides", JOURNAL OF LASER MICRO/NANOENGINEERING, vol. 6, no. 3, 1 December 2011 (2011-12-01), pages 195 - 198, XP055129252, DOI: 10.2961/jlmn.2011.03.0004 *

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107298860A (zh) * 2016-09-12 2017-10-27 宁波创导三维医疗科技有限公司 一种硅胶3d打印机及其打印方法
US11104802B2 (en) 2016-09-26 2021-08-31 University Of Washington PDMS resin for stereolithographic 3D-printing of PDMS
WO2018151850A1 (fr) * 2017-02-16 2018-08-23 Arizona Board Of Regents On Behalf Of The University Of Arizona Fabrication additive assistée par laser d'optiques utilisant des matériaux thermiquement durcissables
WO2018234643A1 (fr) 2017-06-22 2018-12-27 Elkem Silicones France Sas Photoamorceurs radicalaires et leurs utilisations dans les compositions silicones
US11629233B2 (en) 2017-06-22 2023-04-18 Elkem Silicones France Sas Free-radical photoinitiators and uses of same in silicone compositions
CN111417672A (zh) * 2017-09-26 2020-07-14 美国圣戈班性能塑料公司 可光致固化组合物及将其用于进行3d打印的方法
US11492504B2 (en) * 2017-09-26 2022-11-08 Saint-Gobain Performance Plastics Corporation Photocurable compositions and methods for 3D printing using them
EP3694907A4 (fr) * 2017-09-26 2021-08-18 Saint-Gobain Performance Plastics Corporation Compositions photodurcissables et procédés d'impression 3d les utilisant
CN111093949A (zh) * 2017-11-22 2020-05-01 麦克赛尔控股株式会社 模型材用组合物
US11597786B2 (en) 2017-11-22 2023-03-07 Maxell, Ltd. Composition for model material
EP3715094A4 (fr) * 2017-11-22 2021-09-08 Maxell Holdings, Ltd. Composition pour matériau de modèle
JP2019093639A (ja) * 2017-11-22 2019-06-20 マクセルホールディングス株式会社 モデル材用組成物
CN111093949B (zh) * 2017-11-22 2022-06-24 麦克赛尔株式会社 模型材用组合物
WO2019102695A1 (fr) * 2017-11-22 2019-05-31 マクセルホールディングス株式会社 Composition pour matériau de modèle
WO2020016282A1 (fr) * 2018-07-20 2020-01-23 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Fabrication de corps moulés à partir d'un polymère hybride inorganique-organique à haute résolution par impression 3d, corps moulés à résistances élevées à la flexion et à modules d'élasticité élevés ainsi que leur utilisation à des fins dentaires
US11618211B2 (en) 2018-07-20 2023-04-04 Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. Production of molded bodies from an inorganic-organic hybrid polymer with high resolution using 3D printing, molded bodies with a high flexural strength and elastic modulus, and the use thereof for dental purposes
WO2020059650A1 (fr) * 2018-09-20 2020-03-26 信越化学工業株式会社 Composition de silicone durcissable par rayonnement uv et son produit durci
US12180320B2 (en) 2018-09-20 2024-12-31 Shin-Etsu Chemical Co., Ltd. Ultraviolet curable silicone composition and cured product thereof
WO2020080011A1 (fr) * 2018-10-19 2020-04-23 信越化学工業株式会社 Composition de silicone durcissable aux uv et produit durci associé
US11976172B2 (en) 2019-04-16 2024-05-07 Saint-Gobain Performance Plastics Corporation Dual cure compositions
US11945935B2 (en) 2019-05-08 2024-04-02 Saint-Gobain Performance Plastics Corporation Hydrophilic polymer compositions
CN113811436A (zh) * 2019-05-13 2021-12-17 汉高股份有限及两合公司 可辐射固化且可印刷的聚硅氧烷组合物
US11958240B2 (en) 2019-08-08 2024-04-16 Hewlett-Packard Development Company, L.P. Three-dimensional printing with organosilanes
US11993010B2 (en) 2019-08-08 2024-05-28 Hewlett-Packard Development Company, L.P. Three-dimensional printing
EP3981578A1 (fr) * 2020-10-06 2022-04-13 Sumitomo Rubber Industries, Ltd. Composition de polymère pour stéréolithographie
US11944553B2 (en) 2021-01-08 2024-04-02 DePuy Synthes Products, Inc. Expanding spinal fusion cage
WO2022240961A1 (fr) 2021-05-12 2022-11-17 Elkem Silicones USA Corp. Procédé de production d'un article imprimé tridimensionnel
WO2022240955A1 (fr) 2021-05-12 2022-11-17 Elkem Silicones USA Corp. Procédé de production d'un article imprimé tridimensionnel
US11964425B2 (en) 2021-05-12 2024-04-23 Elkem Silicones USA Corp. Method for producing a three-dimensional printed article
EP4344873A1 (fr) 2022-09-27 2024-04-03 Elkem Silicones France SAS Post-traitement d'un article en silicone élastomère imprimé en 3d
WO2024068044A1 (fr) 2022-09-27 2024-04-04 Elkem Silicones France Sas Post-traitement d'un article en silicone élastomère imprimé en 3d

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