CA2028537A1 - Methode pour regler la sensibilite au rayonnement des composes photopolymerisables - Google Patents

Methode pour regler la sensibilite au rayonnement des composes photopolymerisables

Info

Publication number
CA2028537A1
CA2028537A1 CA2028537A CA2028537A CA2028537A1 CA 2028537 A1 CA2028537 A1 CA 2028537A1 CA 2028537 A CA2028537 A CA 2028537A CA 2028537 A CA2028537 A CA 2028537A CA 2028537 A1 CA2028537 A1 CA 2028537A1
Authority
CA
Canada
Prior art keywords
radiation
sensitivity
adjusting
photopolymerizable compositions
photoinitiators
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.)
Granted
Application number
CA2028537A
Other languages
English (en)
Other versions
CA2028537C (fr
Inventor
Manfred Hofmann
Bernd Klingert
Max Hunziker
Rolf Wiesendanger
Adrian Schulthess
Paul Bernhard
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.)
Huntsman Advanced Materials Switzerland GmbH
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of CA2028537A1 publication Critical patent/CA2028537A1/fr
Application granted granted Critical
Publication of CA2028537C publication Critical patent/CA2028537C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031Organic compounds not covered by group G03F7/029
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive 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
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive 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
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124Processes 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
    • B29C64/129Processes 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 characterised by the energy source therefor, e.g. by global irradiation combined with a mask
    • B29C64/135Processes 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 characterised by the energy source therefor, e.g. by global irradiation combined with a mask the energy source being concentrated, e.g. scanning lasers or focused light sources
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE 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
    • B33Y10/00Processes of additive manufacturing
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE 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
    • B33Y70/00Materials specially adapted for additive manufacturing
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0037Production of three-dimensional images
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Polymerisation Methods In General (AREA)
  • Polymerization Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
CA002028537A 1989-10-27 1990-10-25 Methode pour regler la sensibilite au rayonnement des composes photopolymerisables Expired - Fee Related CA2028537C (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3901/89-0 1989-10-27
CH390189 1989-10-27

Publications (2)

Publication Number Publication Date
CA2028537A1 true CA2028537A1 (fr) 1991-04-28
CA2028537C CA2028537C (fr) 2000-01-25

Family

ID=4265938

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002028537A Expired - Fee Related CA2028537C (fr) 1989-10-27 1990-10-25 Methode pour regler la sensibilite au rayonnement des composes photopolymerisables

Country Status (7)

Country Link
US (2) US5573889A (fr)
EP (1) EP0425440B1 (fr)
JP (1) JP3099126B2 (fr)
KR (1) KR0155169B1 (fr)
CA (1) CA2028537C (fr)
DE (1) DE59007720D1 (fr)
HK (1) HK1004762A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5418112A (en) * 1993-11-10 1995-05-23 W. R. Grace & Co.-Conn. Photosensitive compositions useful in three-dimensional part-building and having improved photospeed

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487086B2 (fr) * 1990-11-22 2008-08-13 Canon Kabushiki Kaisha Méthode pour fabriquer un hologramme de phase épais utilisant un milieu d'enregistrement photosensible
JP2873126B2 (ja) * 1991-04-17 1999-03-24 日本ペイント株式会社 体積ホログラム記録用感光性組成物
JPH0586149A (ja) * 1991-09-30 1993-04-06 I C I Japan Kk 光立体成形用樹脂組成物並びに立体成形体の形成方法
TW311923B (fr) * 1992-01-27 1997-08-01 Ciba Sc Holding Ag
JPH05287008A (ja) * 1992-04-08 1993-11-02 Tokuyama Soda Co Ltd 光重合性組成物及びその重合方法
DE4424101A1 (de) * 1994-07-08 1996-01-11 Basf Lacke & Farben Strahlenhärtbare Lacke und deren Verwendung zur Herstellung matter Lackfilme
JP3478630B2 (ja) * 1995-02-09 2003-12-15 富士写真フイルム株式会社 光重合性組成物
USRE37962E1 (en) * 1995-02-28 2003-01-07 Fuji Photo Film Co., Ltd. Photopolymerizable composition containing a sensitizing dye and a titanocene compound
US5700849A (en) * 1996-02-23 1997-12-23 Fuji Photo Film Co., Ltd. Photopolymerizable composition containing a sensitizing dye and a titanocene compound
GB9504995D0 (en) * 1995-03-11 1995-04-26 Zeneca Ltd Compositions
US5731363A (en) * 1995-03-20 1998-03-24 Fuji Photo Film Co., Ltd. Photopolymerizable composition containing sensitizing dye and titanocene compound
US5707780A (en) * 1995-06-07 1998-01-13 E. I. Du Pont De Nemours And Company Photohardenable epoxy composition
JP3651713B2 (ja) * 1996-02-29 2005-05-25 富士写真フイルム株式会社 光重合性組成物
EP0897558B1 (fr) 1996-05-09 2000-09-27 Dsm N.V. Composition de resine photosensible destinee au prototypage rapide et procede de production d'objets tridimensionnels
DE69716260D1 (de) * 1996-05-20 2002-11-14 Albemarle Corp Photoaktive verbindungen verwendbar mit enger wellenlänge band ultraviolet (uv) härtende systeme
US6479706B1 (en) 1997-02-04 2002-11-12 Albemarle Corporation Aminobenzophenones and photopolymerizable compositions including the same
US6473220B1 (en) 1998-01-22 2002-10-29 Trivium Technologies, Inc. Film having transmissive and reflective properties
US6043294A (en) * 1998-01-29 2000-03-28 Gate Technologies International, Inc. Method of and apparatus for optically enhancing chemical reactions
US6149856A (en) * 1998-11-13 2000-11-21 Anvik Corporation Ultraviolet-based, large-area scanning system for photothermal processing of composite structures
CA2388046A1 (fr) 1999-11-05 2001-05-17 Z Corporation Systemes de produit et procedes pour impression tridimensionnelle
US6579664B2 (en) * 2001-03-30 2003-06-17 Napp Systems, Inc. High performance, photoimageable resin compositions and printing plates prepared therefrom
JP3938684B2 (ja) * 2001-12-11 2007-06-27 株式会社豊田中央研究所 自己形成光導波路材料組成物
US7345824B2 (en) 2002-03-26 2008-03-18 Trivium Technologies, Inc. Light collimating device
US7595934B2 (en) 2002-03-26 2009-09-29 Brilliant Film Llc Integrated sub-assembly having a light collimating or transflecting device
WO2004104677A2 (fr) * 2003-05-20 2004-12-02 Trivium Technologies, Inc. Dispositifs a utiliser dans des afficheurs passifs
JP4360242B2 (ja) * 2004-03-24 2009-11-11 Jsr株式会社 ネガ型感放射線性樹脂組成物
WO2006107759A2 (fr) * 2005-04-01 2006-10-12 3 Birds, Inc. Resines de stereolithographie et procedes associes
WO2008073297A2 (fr) 2006-12-08 2008-06-19 Z Corporation Système de matériaux d'impression tridimensionnelle et procédé utilisant un durcissement au peroxyde
WO2008086033A1 (fr) 2007-01-10 2008-07-17 Z Corporation Système de matériau d'impression tridimensionnel avec une couleur, une performance de l'article et une facilité d'utilisation améliorées
US7968626B2 (en) 2007-02-22 2011-06-28 Z Corporation Three dimensional printing material system and method using plasticizer-assisted sintering
WO2009108896A1 (fr) 2008-02-27 2009-09-03 Brilliant Film, Llc Concentrateurs pour systèmes de génération d’énergie solaire
US11865785B2 (en) * 2010-08-20 2024-01-09 H. David Dean Continuous digital light processing additive manufacturing of implants
US9688023B2 (en) * 2010-08-20 2017-06-27 H. David Dean Continuous digital light processing additive manufacturing of implants
JP6543974B2 (ja) * 2015-03-16 2019-07-17 東洋インキScホールディングス株式会社 光学的立体造形用活性エネルギー線重合性樹脂組成物、及び立体造形物
US10668708B2 (en) * 2016-09-27 2020-06-02 Lawrence Livermore National Security, Llc Optically enhanced patternable photosensitivity via oxygen excitation
US11117316B2 (en) * 2016-11-04 2021-09-14 Carbon, Inc. Continuous liquid interface production with upconversion photopolymerization
EP3585301B1 (fr) 2017-02-22 2024-05-01 Inter-Med, Inc. Dispositif de chauffage et de distribution de materiel dentaire
JP6943950B2 (ja) * 2017-03-29 2021-10-06 三井化学株式会社 光硬化性組成物、義歯床及び有床義歯
US11904031B2 (en) 2017-11-22 2024-02-20 3M Innovative Properties Company Orthodontic articles comprising polymerized composition comprising at least two free-radical initiators
EP3813763A1 (fr) 2018-06-29 2021-05-05 3M Innovative Properties Company Articles orthodontiques comprenant une composition polymérisable par polymérisation radicalaire et durcie, offrant une résistance améliorée dans un environnement aqueux
CN114249995B (zh) 2020-09-23 2022-12-13 上海飞凯材料科技股份有限公司 一种紫外固化涂料组合物及其应用

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3661576A (en) * 1970-02-09 1972-05-09 Brady Co W H Photopolymerizable compositions and articles
US3903322A (en) * 1974-03-07 1975-09-02 Continental Can Co Photopolymerizable ethylenically unsaturated compounds photoinitiated with benzoyl derivatives of diphenyl sulfide and an organic amine compound
BR7700555A (pt) * 1976-02-02 1977-10-04 Eastman Kodak Co Composicao fotossensivel e respectivo elemento fotografic
US4147552A (en) * 1976-05-21 1979-04-03 Eastman Kodak Company Light-sensitive compositions with 3-substituted coumarin compounds as spectral sensitizers
US4100141A (en) * 1976-07-02 1978-07-11 Loctite (Ireland) Limited Stabilized adhesive and curing compositions
DE2931737A1 (de) * 1979-08-04 1981-02-26 Basf Ag Verfahren zur herstellung von formkoerpern aus ungesaettigten polyesterharzen
JPS57148740A (en) * 1981-03-10 1982-09-14 Toyobo Co Ltd Image duplicating material
US4535052A (en) * 1983-05-02 1985-08-13 E. I. Du Pont De Nemours And Company Constrained n-alkylamino aryl ketones as sensitizers for photopolymer compositions
US4590145A (en) * 1985-06-28 1986-05-20 Daicel Chemical Industries, Ltd. Photopolymerization initiator comprised of thioxanthones and oxime esters
EP0210637B1 (fr) * 1985-07-31 1991-09-11 E.I. Du Pont De Nemours And Company Composition optique de couchage
AU599400B2 (en) * 1986-08-01 1990-07-19 Ciba-Geigy Ag Titanocenes and their use
US4985472A (en) * 1987-05-01 1991-01-15 Mitsubishi Rayon Company, Ltd. Actinic ray curable composition for casting polymerization and casting polymerization molded products
GB8714864D0 (en) * 1987-06-25 1987-07-29 Ciba Geigy Ag Photopolymerizable composition ii
GB8715435D0 (en) * 1987-07-01 1987-08-05 Ciba Geigy Ag Forming images
US4845011A (en) * 1987-10-23 1989-07-04 Hoechst Celanese Corporation Visible light photoinitiation compositions
DE3743455A1 (de) * 1987-12-22 1989-07-06 Hoechst Ag Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial
US4942001A (en) * 1988-03-02 1990-07-17 Inc. DeSoto Method of forming a three-dimensional object by stereolithography and composition therefore
US4945032A (en) * 1988-03-31 1990-07-31 Desoto, Inc. Stereolithography using repeated exposures to increase strength and reduce distortion
US5182056A (en) * 1988-04-18 1993-01-26 3D Systems, Inc. Stereolithography method and apparatus employing various penetration depths
US5059359A (en) * 1988-04-18 1991-10-22 3 D Systems, Inc. Methods and apparatus for production of three-dimensional objects by stereolithography
US5076974A (en) * 1988-04-18 1991-12-31 3 D Systems, Inc. Methods of curing partially polymerized parts
US5219896A (en) * 1989-09-06 1993-06-15 Stamicarbon, B.V. Primary coatings for optical glass fibers including poly(carbonate-urethane) acrylates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5418112A (en) * 1993-11-10 1995-05-23 W. R. Grace & Co.-Conn. Photosensitive compositions useful in three-dimensional part-building and having improved photospeed

Also Published As

Publication number Publication date
EP0425440B1 (fr) 1994-11-17
KR0155169B1 (ko) 1998-12-01
DE59007720D1 (de) 1994-12-22
JPH03160001A (ja) 1991-07-10
US5573889A (en) 1996-11-12
US5645973A (en) 1997-07-08
EP0425440A1 (fr) 1991-05-02
KR910007967A (ko) 1991-05-30
JP3099126B2 (ja) 2000-10-16
CA2028537C (fr) 2000-01-25
HK1004762A1 (en) 1998-12-04

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Legal Events

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Effective date: 20031027