ES2583103T3 - Placas de impresión sensibles a IR revelables en prensa que utilizan resinas ligantes que tienen segmentos de óxido de polietileno - Google Patents

Placas de impresión sensibles a IR revelables en prensa que utilizan resinas ligantes que tienen segmentos de óxido de polietileno Download PDF

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ES2583103T3
ES2583103T3 ES03718373.8T ES03718373T ES2583103T3 ES 2583103 T3 ES2583103 T3 ES 2583103T3 ES 03718373 T ES03718373 T ES 03718373T ES 2583103 T3 ES2583103 T3 ES 2583103T3
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polyethylene oxide
sensitive
block
binding agent
press
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Jianbing Huang
Heidi M. Munnelly
Shashikant Saraiya
Socrates Peter Pappas
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Eastman Kodak Co
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Eastman Kodak Co
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41CPROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C1/00Forme preparation
    • B41C1/10Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme
    • B41C1/1008Forme preparation for lithographic printing; Master sheets for transferring a lithographic image to the forme by removal or destruction of lithographic material on the lithographic support, e.g. by laser or spark ablation; by the use of materials rendered soluble or insoluble by heat exposure, e.g. by heat produced from a light to heat transforming system; by on-the-press exposure or on-the-press development, e.g. by the fountain of photolithographic materials
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/36Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using a polymeric layer, which may be particulate and which is deformed or structurally changed with modification of its' properties, e.g. of its' optical hydrophobic-hydrophilic, solubility or permeability properties
    • B41M5/368Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using a polymeric layer, which may be particulate and which is deformed or structurally changed with modification of its' properties, e.g. of its' optical hydrophobic-hydrophilic, solubility or permeability properties involving the creation of a soluble/insoluble or hydrophilic/hydrophobic permeability pattern; Peel development
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/04Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/494Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498Photothermographic systems, e.g. dry silver
    • G03C1/49836Additives
    • G03C1/49863Inert additives, e.g. surfactants, binders
    • 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
    • G03F7/016Diazonium salts or compounds
    • G03F7/021Macromolecular diazonium compounds; Macromolecular additives, e.g. binders
    • G03F7/0212Macromolecular diazonium compounds; Macromolecular additives, e.g. binders characterised by the polymeric binder or the macromolecular additives other than the diazo resins or the polymeric diazonium compounds
    • 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
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41CPROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/04Negative working, i.e. the non-exposed (non-imaged) areas are removed
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41CPROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/08Developable by water or the fountain solution
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41CPROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES
    • B41C2210/00Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation
    • B41C2210/24Preparation or type or constituents of the imaging layers, in relation to lithographic printing forme preparation characterised by a macromolecular compound or binder obtained by reactions involving carbon-to-carbon unsaturated bonds, e.g. acrylics, vinyl polymers
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging 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
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/106Binder containing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging 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
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/114Initiator containing
    • Y10S430/117Free radical
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/145Infrared

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Thermal Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Materials For Photolithography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Graft Or Block Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

Una placa de impresión litográfica de trabajo negativo que comprende (a) un sustrato y (b) aplicada al sustrato una capa de trabajo negativo que comprende una composición polimerizable que comprende (i) un compuesto polimerizable, y (ii) un agente ligante polimérico; en donde el agente ligante polimérico comprende segmentos de óxido de polietileno y se selecciona de por lo menos un copolímero de injerto que comprende un polímero de cadena principal y cadenas laterales de óxido de polietileno, un copolímero en bloque que tiene por lo menos un bloque de óxido de polietileno y por lo menos un bloque de óxido de no polietileno, y una combinación de los mismos; en donde los segmentos de óxido de polietileno de las cadenas laterales de óxido de polietileno o el bloque de óxido de polietileno tienen un peso molecular promedio en número que varía de 500 a 10.000; en donde la composición polimerizable comprende partículas separadas del agente ligante polimérico que se encuentran suspendidas en la composición polimerizable; y en donde la proporción de peso del compuesto polimerizable y el agente ligante polimérico varía de 5:95 a 95:5.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
o
imagen7
en donde cada uno de R7, R8, R9 y R10 es hidrógeno; R3 puede ser H o alquilo; y n es de aproximadamente 12 a
5 aproximadamente 250. El segmento hidrofóbico en W puede ser -R12 -, -O-R12—0-, -R3N-R12 -NR3-, —OOC-R12-O-o -OOC-R12 —O-, en donde cada R12 puede ser en forma independiente un alquileno lineal, ramificado o cíclico de 6 a 120 átomos de carbono, un haloalquileno de 6 a 120 átomos de carbono, un arileno de 6 a 120 átomos de carbono, un alcarileno de 6 a 120 átomos de carbono o un aralquileno de 6 a 120 átomos de carbono; y R3 puede ser H o alquilo.
10 El segmento hidrofílico en Y puede ser H, R15, OH, OR16, COOH, COOR16, O2CR16, un segmento representado por la fórmula:
imagen8
R14
15 en donde cada uno de R7, R8, R9 Y R10 es hidrógeno; R3 puede ser H o alquilo; en donde cada R13, , R15 Y R16 puede ser en forma independiente H o alquilo de 1 a 5 átomos de carbono y n es de aproximadamente 12 a aproximadamente 250. El segmento hidrofóbico en Y puede ser un alquilo lineal, ramificado o cíclico de 6 a 120 átomos de carbono, un haloalquilo de 6 a 120 átomos de carbono, un arilo de 6 a 120 átomos de carbono, un alcarilo de 6 a 120 átomos de carbono, un aralquilo de 6 a 120 átomos de carbono, OR17, COOR17 u O2CR17, en donde R17
20 es un alquilo de 6 a 20 átomos de carbono.
En una realización preferida, el copolímero de injerto comprende unidades de repetición representadas por la fórmula:
imagen9
en donde cada uno de R1 y R2 puede ser en forma independiente H, alquilo, arilo, aralquilo, alcarilo, COOR5, R6CO, 25 halógeno o ciano;
en donde Q puede ser uno de:
8
imagen10
imagen11
El copolímero de injerto que tiene segmentos hidrofóbicos y/o hidrofílicos se pueden preparar por medio de un proceso que comprende los pasos de
(A)
poner en contacto los siguientes componentes para producir un copolímero de injerto polimerizable:
(i)
un compuesto representado por la fórmula:
5 H-W-Y
en donde W se selecciona del grupo que consiste en: un segmento hidrofílico y un segmento hidrofóbico e Y se selecciona del grupo que consiste en: un segmento hidrofílico y un segmento hidrofóbico, con la condición de que cuando W es un segmento hidrofílico, Y se seleccione del grupo que consiste en: un segmento hidrofílico y un segmento hidrofóbico, con la condición adicional de que cuando W es hidrofóbico, Y sea un segmento hidrofílico, y
10 (ii) un monómero polimerizable seleccionado del grupo que consiste en compuestos representado por la fórmula:
imagen12
en donde cada R1 se selecciona en forma independiente del grupo que consiste en H, alquilo, arilo, aralquilo,
15 alcarilo, COOR5, R6CO, halógeno y ciano; R4 se selecciona del grupo que consiste en H, alquilo, halógeno, ciano, nitro, alcoxi, alcoxicarbonilo, acilo y una combinación de los mismos; y X es glicidiloxi o un grupo saliente seleccionado entre el grupo que consiste en: halógeno, alcoxi o ariloxi, para producir un monómero de injerto polimerizable; y
(B) la copolimerización del monómero de injerto polimerizable y uno o más comonómeros a una temperatura y
20 durante un periodo de tiempo suficiente para producir el copolímero de injerto. Cuando sea necesario, la etapa de contacto se lleva a cabo en presencia de un catalizador.
Preferiblemente, el comonómero es uno o más de los siguientes: estireno, estireno sustituido, alfa-metilestireno, éster de acrilato, éster de metacrilato, acrilonitrilo, acrilamida, metacrilamida, haluro de vinilo, éster de vinilo, éter de vinilo y una alfa-olefina.
25 El monómero polimerizable preferido puede ser cualquier monómero que sea capaz de reaccionar con H-W-Y e incluya monómeros polimerizables, tales como, m-isopropenil-α, isocianato de α-dimetilbencilo, cloruro de acriloilo y cloruro de metacriloilo. La reacción se lleva a cabo típicamente en presencia de un catalizador, que es preferiblemente una base, un compuesto de estaño o una mezcla de los mismos. En una reacción que admite un catalizador ácido, se puede utilizar un catalizador ácido tal como un ácido de Lewis o prótico.
30 Preferiblemente, los compuestos representados por la fórmula H-W-Y pueden ser uno o más de los compuestos representado por la fórmula:
11
imagen13
imagen14
imagen15
imagen16
5
10
15
20
poliacrílico, se aplicó la solución descrita en la Tabla 2 para proporcionar un peso de recubrimiento seco de 1,3 g/m2.
Tabla 2. Composición del Ejemplo 5 (formulación en partes en peso)
Componente
Partes en peso
Porcentaje
Producto de reacción de DESMODUR®
2,44
N100 con acrilato de hidroxietilo y triacrilato de pentaeritritol
Copolímero de injerto 1
2,22
Sartomer 3551
0,51
Cloruro de difenilyodonio2
0,29
Ácido anilino-N,N-diacético
0,23
Cetocumarina 934
0,06
Byk 3073
0,02
n-Propanol
75,38
Agua
18,85
1 Sartomer 355 es un monómero acrílico multifuncional disponible a través de Sartomer Co., Inc. 2 Cloruro de difenilyodonio de Aldrich. 3 Byk 307 es un polisiloxano modificado disponible a través de Byk Chemie. 4 Cetocumarina 93 tiene la siguiente estructura:
imagen17
Luego se sobrerrecubrió el recubrimiento resultante de acuerdo con lo descrito en el Ejemplo 3 para proporcionar un peso de recubrimiento seco de 2 g/m2. Se reflejó la placa resultante en un Simulador Solar Oriel de 1000 W modelo #81291 (Oriel Instruments, Stratford, CT) equipada con un filtro de ejecución 530 durante 5 segundos a 4 mW/cm2.
Se procesó la placa en una pileta con agua y una solución de 30% Varn 142W/30% Varn Par, luego se montó directamente en una prensa AB Dick. La placa imprimió más de 500 copias de impresiones de buena calidad.
Ejemplo 6: Síntesis del Copolímero de injerto 2:
Se cargaron agua desionizada (314,8 g) y dodecilsulfato de sodio (2,0 g) en un matraz de 4 bocas de un litro bajo atmósfera de nitrógeno y se calentaron a 70°C. Se añadieron una premezcla de persulfato de amonio (0,65 g) y agua desionizada (20 g) a 70°C en 15 minutos. Se añadieron una premezcla de estireno (79,5 g), el Macrómero 1 (10 g) y ácido acrílico (7,9 g) en 3 horas a 70°C. Una hora y media más tarde, se halló que los % de no volátiles fueron de 22,5% frente a 23% (teórico). Se enfrió la mezcla de reacción a temperatura ambiente con agua. Se añadió una solución de hidróxido de amonio (8 g) a temperatura ambiente para estabilizar el látex.
Ejemplo 7: Preparación de una placa de impresión sensible a IR
Se repitió el Ejemplo 3 excepto que no se aplicó sobrerrecubrimiento y se reemplazó el Copolímero de injerto 1 por el Copolímero de injerto 2 para ilustrar el efecto del número de ácido ligante. La Figura 1 muestra un análisis de escaneo de microscopio electrónico (`SEM’) del recubrimiento resultante. De acuerdo con lo mostrado en la Figura 1, el recubrimiento comprende partículas separadas. El diámetro de las partículas es hasta aproximadamente 60 nm.
16
imagen18
imagen19
imagen20

Claims (1)

  1. imagen1
ES03718373.8T 2002-04-10 2003-04-10 Placas de impresión sensibles a IR revelables en prensa que utilizan resinas ligantes que tienen segmentos de óxido de polietileno Expired - Lifetime ES2583103T3 (es)

Applications Claiming Priority (3)

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US119454 2002-04-10
US10/119,454 US6899994B2 (en) 2001-04-04 2002-04-10 On-press developable IR sensitive printing plates using binder resins having polyethylene oxide segments
PCT/US2003/011358 WO2003087939A2 (en) 2002-04-10 2003-04-10 On-press developable ir sensitive printing plates using binder resins having polyethylene oxide segments

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EP (1) EP1493058B1 (es)
JP (3) JP2005522362A (es)
KR (1) KR100953771B1 (es)
CN (1) CN100495207C (es)
AU (1) AU2003221914B2 (es)
BR (1) BR0309165A (es)
CA (1) CA2479515A1 (es)
ES (1) ES2583103T3 (es)
HK (1) HK1079578A1 (es)
RU (1) RU2300792C2 (es)
WO (1) WO2003087939A2 (es)
ZA (1) ZA200408146B (es)

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BR0309165A (pt) 2005-01-25
KR20040106325A (ko) 2004-12-17
HK1079578A1 (en) 2006-04-07
US20050170286A1 (en) 2005-08-04
CN100495207C (zh) 2009-06-03
CN1650233A (zh) 2005-08-03
EP1493058A2 (en) 2005-01-05
JP2005522362A (ja) 2005-07-28
EP1493058B1 (en) 2016-06-22
US20030064318A1 (en) 2003-04-03
ZA200408146B (en) 2005-11-30
JP2013107399A (ja) 2013-06-06
US7258964B2 (en) 2007-08-21
JP2009234268A (ja) 2009-10-15
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AU2003221914B2 (en) 2008-03-06
RU2300792C2 (ru) 2007-06-10
CA2479515A1 (en) 2003-10-23
WO2003087939A3 (en) 2004-03-04
RU2004132874A (ru) 2005-06-10
US6899994B2 (en) 2005-05-31
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WO2003087939A2 (en) 2003-10-23
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