CA2326128A1 - Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography - Google Patents

Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography

Info

Publication number
CA2326128A1
CA2326128A1 CA002326128A CA2326128A CA2326128A1 CA 2326128 A1 CA2326128 A1 CA 2326128A1 CA 002326128 A CA002326128 A CA 002326128A CA 2326128 A CA2326128 A CA 2326128A CA 2326128 A1 CA2326128 A1 CA 2326128A1
Authority
CA
Canada
Prior art keywords
polyether polyol
radiation
cationic
stereolithography
reactive
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
CA002326128A
Other languages
French (fr)
Other versions
CA2326128C (en
Inventor
Anastasios Panayiotis Melisaris
Renyi Wang
Thomas Hsing Pang
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
Individual
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 Individual filed Critical Individual
Publication of CA2326128A1 publication Critical patent/CA2326128A1/en
Application granted granted Critical
Publication of CA2326128C publication Critical patent/CA2326128C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0037—Production of three-dimensional images
    • 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
    • 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
    • B33Y70/10—Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C9/00—Stereo-photographic or similar processes
    • G03C9/08—Producing three-dimensional images
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Abstract

The present invention relates to stereolithographic compositions containing an actinic radiation-curable and cationically polymerizable organic substance, a cationic initiator, a radical photoinitiator, and at least one cationic reactive modifier containing at least two reactive groups per molecule or at least one polyether polyol or mixtures thereof. The cationic reactive modifier has at least one chain extension segment with a molecular weight of at least about 100 and not more than about 2,000. The polyether polyol has a molecular weight greater than or equal to about 4,000. The use of the cationically reactive modifiers and polyether polyol modifiers substantially increases the fexibility and toughness of the cured articles without compromising photospeed, accuracy and wetting-recoatability of the compositions.
The present invention further relates to a method of producing a cured product, particularly three-dimensional shaped articles by treating the composition described above with actinic radiation.
CA002326128A 1998-03-30 1999-03-19 Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography Expired - Lifetime CA2326128C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/050,279 1998-03-30
US09/050,279 US6136497A (en) 1998-03-30 1998-03-30 Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography
PCT/EP1999/001844 WO1999050711A1 (en) 1998-03-30 1999-03-19 Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography

Publications (2)

Publication Number Publication Date
CA2326128A1 true CA2326128A1 (en) 1999-10-07
CA2326128C CA2326128C (en) 2008-07-15

Family

ID=21964363

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002326128A Expired - Lifetime CA2326128C (en) 1998-03-30 1999-03-19 Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography

Country Status (15)

Country Link
US (3) US6136497A (en)
EP (1) EP1080392B1 (en)
JP (1) JP4798845B2 (en)
KR (1) KR100653732B1 (en)
CN (1) CN1191498C (en)
AT (1) ATE399335T1 (en)
AU (1) AU3518699A (en)
BR (1) BR9909270A (en)
CA (1) CA2326128C (en)
DE (1) DE69938966D1 (en)
HK (1) HK1032635A1 (en)
IL (1) IL138301A0 (en)
TR (1) TR200002776T2 (en)
TW (1) TWI221850B (en)
WO (1) WO1999050711A1 (en)

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Also Published As

Publication number Publication date
AU3518699A (en) 1999-10-18
EP1080392B1 (en) 2008-06-25
EP1080392A1 (en) 2001-03-07
DE69938966D1 (en) 2008-08-07
KR20010042325A (en) 2001-05-25
TWI221850B (en) 2004-10-11
WO1999050711A1 (en) 1999-10-07
BR9909270A (en) 2000-11-21
US20020177073A1 (en) 2002-11-28
CA2326128C (en) 2008-07-15
HK1032635A1 (en) 2001-07-27
TR200002776T2 (en) 2001-02-21
CN1191498C (en) 2005-03-02
IL138301A0 (en) 2001-10-31
JP2002509982A (en) 2002-04-02
JP4798845B2 (en) 2011-10-19
US6136497A (en) 2000-10-24
ATE399335T1 (en) 2008-07-15
CN1296577A (en) 2001-05-23
KR100653732B1 (en) 2006-12-05
US6413697B1 (en) 2002-07-02

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