CA2189459A1 - Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates - Google Patents

Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates

Info

Publication number
CA2189459A1
CA2189459A1 CA002189459A CA2189459A CA2189459A1 CA 2189459 A1 CA2189459 A1 CA 2189459A1 CA 002189459 A CA002189459 A CA 002189459A CA 2189459 A CA2189459 A CA 2189459A CA 2189459 A1 CA2189459 A1 CA 2189459A1
Authority
CA
Canada
Prior art keywords
substituted
group
triazine
phenyl
unsubstituted alkyl
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
CA002189459A
Other languages
French (fr)
Other versions
CA2189459C (en
Inventor
Maurice J. Fitzgerald
Donna J. Guarrera
John M. Hardin
Frederick R. Kearney
Rong-Chang Liang
William C. Schwarzel
John C. Warner
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.)
LATRAN TECHNOLOGIES LLC
Original Assignee
Maurice J. Fitzgerald
Donna J. Guarrera
John M. Hardin
Frederick R. Kearney
Rong-Chang Liang
William C. Schwarzel
John C. Warner
Polaroid Corporation
Pgi Graphics Imaging Llc
Latran Technologies 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 Maurice J. Fitzgerald, Donna J. Guarrera, John M. Hardin, Frederick R. Kearney, Rong-Chang Liang, William C. Schwarzel, John C. Warner, Polaroid Corporation, Pgi Graphics Imaging Llc, Latran Technologies Llc filed Critical Maurice J. Fitzgerald
Publication of CA2189459A1 publication Critical patent/CA2189459A1/en
Application granted granted Critical
Publication of CA2189459C publication Critical patent/CA2189459C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • G03F7/0295—Photolytic halogen compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/12—Nitrogen compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/12—Nitrogen compound containing
    • Y10S430/121—Nitrogen in heterocyclic ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/127—Spectral sensitizer containing

Abstract

The present invention sets forth the incorporation of a substituted 2-phenyl-4,6-bis (trichloromethyl)-1,3,5-triazine in photoresists of lithographic printing plates for the purpose of promoting their shelf-life, room light stability, and developability. The present invention provides a photocurable composition comprising at least a photopolymerizable ethylenically unsaturated monomer having at least one terminal ethylenic group and capable of forming a polymer upon exposure to actinic radiation; and an s-triazine capable of initiating free radical polymerization of the photopolymerizable ethylenically unsaturated monomer and being represented by general formula (I), wherein R1 is either OR4 or NR5R6, wherein R5 and R6 may or may not be identical with each other, either R5 or R6 may represent hydrogen, and wherein R4 and at least one of R5 and R6 represent a ballast group capable of preventing the substantial volatilization of the s-triazine from the photoresist composition, the ballast group being a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, the substituted or unsubstituted alkyl group having at least 4 carbon atoms, the substituted or unsubstituted aryl group having at least 6 carbon atoms; R2 and R3 may or may not be identical with each other and each represents hydrogen, halogen, phenyl, a substituted or unsubstituted alkyl group, or an alkoxyl group; X and Y may or may not be identical with each other and each represent chlorine or bromine;
and m and n may or may not be identical with each other and are each an integer of 0, 1, or 2. Desirable compositions will further comprise at least one photooxidizable leuco triarylmethane dye.
CA002189459A 1995-04-28 1996-04-19 Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates Expired - Fee Related CA2189459C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/430,461 US5561029A (en) 1995-04-28 1995-04-28 Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates
US08/430,461 1995-04-28
PCT/US1996/005517 WO1996034315A1 (en) 1995-04-28 1996-04-19 Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates

Publications (2)

Publication Number Publication Date
CA2189459A1 true CA2189459A1 (en) 1996-10-31
CA2189459C CA2189459C (en) 2006-10-17

Family

ID=23707654

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002189459A Expired - Fee Related CA2189459C (en) 1995-04-28 1996-04-19 Low-volatility, substituted 2-phenyl-4,6-bis (halomethyl)-1,3,5-triazine for lithographic printing plates

Country Status (6)

Country Link
US (1) US5561029A (en)
EP (1) EP0767932B1 (en)
JP (1) JP2968342B2 (en)
CA (1) CA2189459C (en)
DE (1) DE69609136T2 (en)
WO (1) WO1996034315A1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2034274A1 (en) * 1990-02-07 1991-08-08 James A. Bonham Polymers containing halomethyl-1,3,5-triazine moieties
US5506090A (en) * 1994-09-23 1996-04-09 Minnesota Mining And Manufacturing Company Process for making shoot and run printing plates
US5925497A (en) * 1995-04-27 1999-07-20 Minnesota Mining And Manufacturing Company Negative-acting no-process printing plates
US7285422B1 (en) 1997-01-23 2007-10-23 Sequenom, Inc. Systems and methods for preparing and analyzing low volume analyte array elements
US6014929A (en) * 1998-03-09 2000-01-18 Teng; Gary Ganghui Lithographic printing plates having a thin releasable interlayer overlying a rough substrate
DE10022786B4 (en) 1999-05-12 2008-04-10 Kodak Graphic Communications Gmbh On the printing machine developable printing plate
KR100649342B1 (en) 2000-10-30 2006-11-27 시쿼넘, 인코포레이티드 Method and apparatus for delivery of submicroliter volumes onto a substrate
US6495310B2 (en) 2000-10-30 2002-12-17 Gary Ganghui Teng Lithographic plate having conformal overcoat and photosensitive layer on a rough substrate
US6723493B2 (en) 2001-06-04 2004-04-20 Gary Ganghui Teng Negative lithographic printing plate comprising a specific compound in the photosensitive layer
US20090180931A1 (en) 2007-09-17 2009-07-16 Sequenom, Inc. Integrated robotic sample transfer device
CN103376657B (en) * 2013-07-15 2016-12-28 京东方科技集团股份有限公司 Light resistance composition and preparation method thereof, color membrane substrates and display device

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US4189323A (en) * 1977-04-25 1980-02-19 Hoechst Aktiengesellschaft Radiation-sensitive copying composition
JPS6053300B2 (en) * 1978-08-29 1985-11-25 富士写真フイルム株式会社 Photosensitive resin composition
US4330590A (en) * 1980-02-14 1982-05-18 Minnesota Mining And Manufacturing Company Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-2-triazine
US4391687A (en) * 1980-02-14 1983-07-05 Minnesota Mining And Manufacturing Company Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-1-triazine
DE3337024A1 (en) * 1983-10-12 1985-04-25 Hoechst Ag, 6230 Frankfurt LIGHT SENSITIVE COMPOUNDS HAVING TRICHLORMETHYL GROUPS, METHOD FOR THE PRODUCTION THEREOF AND LIGHT SENSITIVE MIXTURE CONTAINING THESE COMPOUNDS
US4851319A (en) * 1985-02-28 1989-07-25 Hoechst Celanese Corporation Radiation polymerizable composition, photographic element, and method of making element with diazonium salt, and monofunctional and polyfunctional acrylic monomers
US4895788A (en) * 1985-08-02 1990-01-23 Hoechst Celanese Corporation Water developable lithographic composition
US4758497A (en) * 1985-08-22 1988-07-19 Polychrome Corporation Photosensitive naphthoquinone diazide sulfonyl ester compounds for the fabrication of lithographic plates and photosensitive sheet construction with the compounds
JPH0766185B2 (en) * 1985-09-09 1995-07-19 富士写真フイルム株式会社 Photosensitive composition
DE3606155A1 (en) * 1986-02-26 1987-08-27 Basf Ag PHOTOPOLYMERIZABLE MIXTURE, THIS CONTAINING LIGHT-SENSITIVE RECORDING ELEMENT, AND METHOD FOR PRODUCING A FLAT PRINT MOLD BY THIS LIGHT-SENSITIVE RECORDING ELEMENT
JPS62212643A (en) * 1986-03-14 1987-09-18 Fuji Photo Film Co Ltd Photopolymerizable composition
US4837128A (en) * 1986-08-08 1989-06-06 Fuji Photo Film Co., Ltd. Light-sensitive composition
JPS6358440A (en) * 1986-08-29 1988-03-14 Fuji Photo Film Co Ltd Photosensitive composition
GB8627059D0 (en) * 1986-11-12 1986-12-10 Cookson Group Plc Substituted trialine derivatives
DE3717933A1 (en) * 1987-05-27 1988-12-08 Hoechst Ag PHOTOPOLYMERIZABLE MIXTURE, THESE RECORDING MATERIAL, AND METHOD FOR PRODUCING HIGH-TEMPERATURE-RESISTANT RELIEF STRUCTURES
GB8719730D0 (en) * 1987-08-20 1987-09-30 Vickers Plc Radiation sensitive compounds
DE3807381A1 (en) * 1988-03-07 1989-09-21 Hoechst Ag HETEROCYCLIC COMPOUNDS CONTAINING 4,6-BIS-TRICHLOROMETHYL-S-TRIAZIN-2-YL-GROUPS, PROCESS FOR THE PREPARATION THEREOF AND LIGHT-SENSITIVE MIXTURE CONTAINING THIS COMPOUND
US5216158A (en) * 1988-03-07 1993-06-01 Hoechst Aktiengesellschaft Oxadiazole compounds containing 4,6-bis-trichloromethyl-S-triazin-2-yl groups, process for their preparation
DE3807378A1 (en) * 1988-03-07 1989-09-21 Hoechst Ag BY 4,6-BIS-TRICHLOROMETHYL-S-TRIAZIN-2-YL-GROUPS SUBSTITUTED AROMATIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN LIGHT-SENSITIVE MIXTURES
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US4985562A (en) * 1988-09-07 1991-01-15 Minnesota Mining And Manufacturing Company Halomethyl-1,3,5-triazines containing an amine-containing moiety
US5116977A (en) * 1988-09-07 1992-05-26 Minnesota Mining And Manufacturing Company Halomethyl-1,3,5-triazines containing an amine-containing moiety
JP2736933B2 (en) * 1990-04-05 1998-04-08 富士写真フイルム株式会社 Photosensitive lithographic printing plate
JPH0480758A (en) * 1990-07-23 1992-03-13 Fuji Photo Film Co Ltd Photosensitive composition
EP0503674B1 (en) * 1991-03-15 1998-06-24 Fuji Photo Film Co., Ltd. Light-sensitive bistrihalomethyl-s-triazine compound and photopolymerizable composition containing same
DE4120173A1 (en) * 1991-06-19 1992-12-24 Hoechst Ag POSITIVELY WORKING RADIATION-SENSITIVE MIXTURE AND PRODUCTION OF RADIATION-SENSITIVE RECORDING MATERIAL THEREFOR
US5298361A (en) * 1991-08-30 1994-03-29 Minnesota Mining And Manufacturing Company Light-sensitive article containing migration-resistant halomethyl-1,3,5-triazine photoinitiator
JPH05341522A (en) * 1992-06-09 1993-12-24 Fuji Photo Film Co Ltd Negative type photoresist composition

Also Published As

Publication number Publication date
JP2968342B2 (en) 1999-10-25
CA2189459C (en) 2006-10-17
US5561029A (en) 1996-10-01
DE69609136T2 (en) 2001-03-22
DE69609136D1 (en) 2000-08-10
WO1996034315A1 (en) 1996-10-31
JPH09505634A (en) 1997-06-03
EP0767932A1 (en) 1997-04-16
EP0767932B1 (en) 2000-07-05

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