US3804628A - Photosensitive compositions comprising a photosensitive polymer and a photochromic compound - Google Patents

Photosensitive compositions comprising a photosensitive polymer and a photochromic compound Download PDF

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Publication number
US3804628A
US3804628A US00265888A US26588872A US3804628A US 3804628 A US3804628 A US 3804628A US 00265888 A US00265888 A US 00265888A US 26588872 A US26588872 A US 26588872A US 3804628 A US3804628 A US 3804628A
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photosensitive
photosensitive composition
set forth
compound
molecular weight
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US00265888A
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C Osada
M Satomura
H Ono
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • 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
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
    • 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

Definitions

  • R represents ahydrogen atom or a methyl group
  • R represents a hydrogen atom, a cyano group or a -COOR group in which R represents a hydrogen atom or an alkyl group havingfrom l to 6 carbon atoms
  • R represents a group, a
  • R represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, an ethyl group, a methoxy group or an ethoxy group
  • R represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, or a halogenated alkyl group
  • R represents a -CH CI-ll group, .a -CH CH- group, or a 34 Claims, 4 Drawing Figures PATENTEDAPR 16 1974 FIG. .I
  • the present invention relates to a photosensitive composition mainly comprising a photosensitive resin having a cinnamoyl group, a B-(2-furyl)acryloyl group or a B-(pyridyUacryloyl group as side chains, an indolinospirobenzopyran derivative which can generate an image coloration immediately upon light exposure, and a sensitizer. More specifically, the present invention relates to a photosensitive composition which shows a strong adhesive property to metals and forms on a metal. surface a photosensitive film or layer which ishardly strippable by rubbing.
  • a polyvinyl cinnamate type photosensitive resin has been widely used as an excellent photosensitive resin but it is poor in its adhesive properties to metals. Accordingly, although such a photosensitive resin is excellent in a system not subjected to abrasion, such as a photoresist, it is unsuitable for a system encountering severe abrasion, such as printing plates.
  • the light exposure and the development of a presensitized lithographic plate are generally carried out as separate operational steps. Therefore, if the latent image formed by the light exposure can be seen, it is quite convenient and such difficulties as double exposure can be prevented. Also, when various kinds of images are printed on a large sheet of photosensitive ma terial, the positions of the images to be printed can be determined readily and at the same time such difficulties as double exposure and blank printing can be prevented if the latent image obtained upon light exposure can be seen.
  • FIG. 1 shows the characteristic curves obtained for a diazo compound and for a indolinobenzospiropyran compound.
  • FIG. 2 shows the wave length region for the light hardening of the photosensitive composition of this invention and the characteristic curve of the spiropyran compound used in this invention.
  • FIG. 3 and 4 are schematic views showing two embodiments of photosensitive materials employing the photosensitive compositions of this invention.
  • Japanese Pat. Publication No. 6413/1969 discloses a diazo compound used as the photosensitive material.
  • the effective energy will be absorbed by the spiropyran compound to suppress the occurence of the photoreaction of the diazo compound since the photosensitive wave length region of the diazo compound almost coincides with the photosensitive wave length region of the spiropyran compound. This results in reducing the sensitivity of the diazo compound. Consequently, the diazo compound.
  • composition containing the spiropyran compound requires a light exposure time of from 2 to 3 times that of the diazo compound composition containing no such spiropyran compound.
  • FIG. 1 of the accompanying drawing the photosensitive wave length region of a diazo compound and the photosensitive spiropyran compound are shown.
  • curve :11 shows the photosensitive wave length region of a general diazo compound
  • curve 12 shows the photosensitive wave length region of a general indolinobenzospiropyran compound.
  • the polyvinyl cinnamate used in Example of Japanese Pat. Publication No. 6413/1969 referred to above has the disadvantage that it is unsuitable for the lithographic printing material as stated in the present invention due to poor printability.
  • a plate is prepared by applying to a support a composition of the photosensitive resin having added thereto a sensitizer and an indolinobenzospiropyran compound.
  • the photosensitive resin used in this invention can be spectrally sensitizedby using a sensitizer, whereby it has a sensitivity at a longer wave than the photosensitive wave length region of the spiropyran compound.
  • the coloring of the spiropyran compound occurs by light of different wave length than that of the light for hardening the. photosensitive resin and thus a visual latent image can be formed without reducing the sensitivity of the photosensitive resin.
  • FIG. 2 of the accompanying drawings the photosensitive wave length region for the light hardening of the photosensitive composition of this invention as curve 21 and the photosensitive wave length region of the spiropyran compound as curve 22 are shown.
  • the shaded portion shows the photosensitive wave length region in which the light hardening reaction occurs without being influenced by the spiropyran compound.
  • the printability of the lithographic printing plate is superior to conventional lithographic printing plates as shown in the following table.
  • Photosensitive Layer 100,000 of this Invention Polyvinyl Cinnamate 20,000 Diazo Compound 40,000
  • the photosensitive resin used in this invention is quite excellent in adhesive properties to metals, printability, and grease receptivity in comparison with a conventional polyvinyl cinnamate as described in Example 5 of Japanese Pat. Publication No. 6413/1969.
  • als can be used at a level of from about 2 to 35 percent by weight, preferably from about to 25 percent by weight, based on the total amount of the polymer.
  • the homopolymers and copolymers of this invention suitably can have molecular weights ranging from 5,000 to 50,000 preferably, from 10,000 to 25,000.
  • sensitizers which can be used in this invention
  • suitable such sensitizers are the aromatic nitro compounds and aromatic keto compounds as 1,2- benzanthraquinon; 2,4,7-trinitro-9-fluorenone; 5- nitroacenaphthene; N-acetyl-4-nitro-l-naphthylamine; N-acetyl-4-nitro-l-naphthylamine; or N-benzoyl-4- nitro-l-naphthylamine and a photosensitive composition sensitized with one of these compounds has the sensitivity toward longer wave length end of the photosensitive wave length region at 450 m p.
  • the amount of the sensitizer to be employed in the photosensitive composition of this invention is generally from 0.5 to percent by weight of the photosensitive resin, preferably from 2 to 7 percent by weight.
  • the spiropyran compound generally is from I to 10 percent by weight, preferably from 2 to 5 percent by weight of the photosensitive resin.
  • the photosensitive compositions of this invention are generally produced by the following manner.
  • the photosensitive high molecular weight compound, the indolinobenzospiropyran compound, and the sensitizer are dissolved in a solvent such as carbon tetrachloride, trichloroethane, dichloroethylene, chlorobenzene, toluene, xylene, ethylene glycol monoethylether acetate, ethylene glycol monomethylether acetate, ethylacetate, butyl acetate, etc, and the solution is applied using conventional techniques onto conventional lithographic plates and dried.
  • a solvent such as carbon tetrachloride, trichloroethane, dichloroethylene, chlorobenzene, toluene, xylene, ethylene glycol monoethylether acetate, ethylene glycol monomethylether acetate, ethylacetate, butyl acetate, etc.
  • a support for example, a metal plate such as an aluminum plate or a copper plate, or a plastic film such as a cellulose acetate or polyethylene terephthalate film can be coated to prepare a photosensitive lithographic material and dried. Suitable coating amounts are from about 0.5 to l,000g/m and for lighographic plates the coating amount generally ranges from about lg to 3g/m
  • the photosensitive composition of this invention may contain a plasticizer such as phthalic acid alkyl diesters having 3 to 12 carbon atoms and other additives such as pigments, dyes, and the like, if desired.
  • the photosensitive composition thus obtained When the photosensitive composition thus obtained is exposed to light such as ultraviolet light, through a photographic negative, the exposed portion is immediately colored and thus the image can be discerned as a visible image.
  • FIG. 3 and FIG. 4 are schematic views showing two embodiments of photosensitive materials employing the photosensitive compositions of this invention.
  • the light curable resin layer 32 containing dispersed therein the light coloring spiropyran compound in an encapsulated state or a molecular state is strongly bonded to a support 31 such as a metal sheet.
  • the light curable resin layer 43 is strongly bonded to the support 41 and also a layer 42 of a high molecular weight compound such as polyvinyl acetate,
  • polyethyl methacrylate, polystyrene, etc, having dispersed therein the light coloring spiropyran compound is strongly bonded to the support.
  • the portion of layer 43 not exposed to light can be readily removed by washing the layer with an organic solvent such as benzene, toluene, xylene, dimethylsulfoxide, N,N-dimethylformamide, 'y-butylolactone, ethylene glycol monoethyl ether acetate, ethylene glycol monoethyl ether acetate, benzyl alcohol, dioxane, tetrahydrofuran, methyl ethyl ketone, acetone, ethyl acetate, etc, after light exposure.
  • an organic solvent such as benzene, toluene, xylene, dimethylsulfoxide, N,N-dimethylformamide, 'y-butylolactone, ethylene glycol monoethyl ether
  • benzopyran were added to the reaction product to provide a photosensitive liquid.
  • the photosensitive liquid was applied to an aluminum sheet for a photosensitive lithographic plate and dried, a coat of a photosensitive composition strongly bonded to the aluminum sheet was formed.
  • the lithographic plate thus formed was placed on an ordinary offset printing machine and printing was conducted using a commercially available ink and wetting water. The results showed that the printing plate was quite excellent in printability, image transfering property, and grease receptivity unaccompanied with the stripping of the layer and thus the employment of the photosensitive resin of this invention was superior to conventional polyvinyl cinnamate.
  • a photosensitive lithographic plate was prepared using the photoconductive composition in the same manner as described in Example 1. By exposing the plate to light through a negative, a visible image was obtained and when printing was conducted using the printing plate and the same procedures as described in Example 1, it was confirmed that the printing plate showed excellent printability unaccompanied by the stripping of the layer.
  • EXAMPLE 3 14 g of glycidyl methacrylate, 16 g of cinnamic acid, and 5 g of triethylamine were dissolved in 240 g of methyl ethyl ketone and after adding to the solution 800 mg of powdered sulfur, the mixture was refluxed for about 10 hours with stirring. After the reaction was,
  • the reaction product was poured in 500 ml of water and 34 g of a faint yellow oily material was obtained.
  • the compound obtained was confirmed to be [By-dicinnamoyloxy-n-propyl methacrylate.
  • 34 g of the monomer thus produced and 2.6 g of methyl methacrylate were dissolved in 100 ml of methyl ethyl ketone and after adding to the solution 340 mg of N,N- azobisisobutyronitrile as the polymerization initiator, the reaction was conducted for about 5 hours at C in a nitrogen atmosphere.
  • the product was added to 200 ml of water and the liquid separated was extracted with ethyl ether.
  • the ether layer formed was separated by decantation, washed with dilute hydrochloric acid and then water, dried over Glaubers salt, and filtered. By distilling away the ether from the ether layer under a reduced pressure, 33 g of a faint yellow oily material was obtained.
  • the oily product was dissolved in 200 g of tetrahydrofuran and after adding 100 mg of N,N'-azobisisobutyronitrile to the solution, the reaction was conducted for about 4 hours in a nitrogen atmosphere. After the reaction was over, the product was added dropwise to n-hexane to obtain a white polymer.
  • EXAMPLE7 14 g of B-cinnamoyloxyethyl methacrylate and 2 g of methyl methacrylate were dissolved in 70 g of methyl ethyl ketone and they were reacted for about 5 hours in a conventional manner. Then, 70 g of methyl ethyl ketone, 800 mg of 5-nitroacenaphthene and 500 mg of l,3,3-trimethyl-6-nitrospiro(indoline-2,2,- benzopyran) were added to the solution to provide a photosensitive liquid. The solution was applied to an aluminum sheet for a photosensitive lithographic plate treated with a zirconium fluoride solution and dried.
  • the printing plate thus prepared was placed on an ordinary offset printing machine and printing was conducted using a commercially available ink and wetting water.
  • the printing plate showed excellent printability and transferring property and printed copies having clear images were obtained.
  • a photosensitive composition comprising (1) an organic solvent soluble photosensitive high molecular weight compound having therein at least one of the units represented by the following general formulae (I) to (V) Ih -CH1C E20 1 CH2 JEEP-OH CH 0CI(
  • 3 CHRa R2 Formula (1) R1 b ...CH
  • R represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, an ethyl group, a methoxy group or an ethoxy group
  • R represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, or a halogenated alkyl group
  • X represents an oxygen atom or a group
  • n represents an integer of from 1 to 4
  • m represents an integer of from 1 to 6, comprising a homopolymer of said units, a copolymer of said units, or a copolymer of said units and units of a monomer copolymerizable therewith
  • (2) a photochromic indolinobenzospiropyran compound and (3) a sensitizer.
  • photosensitive composition as set forth in claim 1, wherein said photosensitive composition sensitized with said sensitizer has a sensitivity toward the longer wave length end of the photosensitive wave length region at a region higher than 430 my, and also has a spectral sensitivity at a longer wave length than the photosensitive wave length region of the photochromic spiropyran compound.
  • photosensitive composition as set forth in claim 1, wherein said photochromic spiropyran compound is sensitive to light having a different wave length from the light to which said sensitized photosensitive compound is sensitive.
  • indolinobenzospiropyran compound is 1,3,3-trimethyl-6'-nitrobis(indoline-2,2'- benzopyran); 1,3,3-trimethyl-6'-nitro-8'- methoxyspiro(indoline-2,2 -benzopyran); 1,3 ,3,5- tetramethyl-6'-nitrospiro(indoline-2,2-benzopyran); l,3,3-trimethyl-5-methoxy-6'-nitrospiro(indoline-2,2'- benzopyran 1,3 ,3-trimethyl5-carbethoxy-6'- nitrospiro(indoline-2,2-benzopyran); l,3,3-trimethyl- 5-chloro-6-nitrospiro(indoline-2,2'-benzopyran); LB- carboxyethyl-3,3-dimethyl-6'-nitrospiro(indoline-2,2'- benzopyran); LB- carboxyethyl
  • a photosensitive element comprising a support having thereon a layer of the photosensitive composition of claim 1.
  • photosensitive composition as set forth in claim 1, whereinsaid photosensitive high molecular weight compoundconsists essentially of a copolymer of said units (I) to (V) as essentially the sole constituents of said copolymer.
  • photosensitive composition as set forth in claim 1, wherein said photosensitive high molecular weight compound comprises a copolymer of at least one of said units'(l) to (V) with units ofa monomer copolymerizable therewith.
  • the photosensitive composition as set forth in claim 12, wherein said monomer copolymerizable therewith is selected from the group consisting of styrene, a-methylstyrene, acrylic acid, methacrylic acid, esters of methanol, ethanol, propanlol, butanol, isobutanol, amyl alcohol, hexyl alcohol, octyl alcohol, lauryl alcohol and stearyl alcohol, acrylic acid, methacrylic acid, acrylamide, acrylonitrile, methacrylonitrile, vinyl chloride, vinyl acetate, B-hydroxycthylrnethacrylatc, N-methylolacrylamide, glycidyl methacrylate, y-chloro-fi-hydroxypropyl methacrylate, glycerol acrylate or glycerol methacrylate. 7
  • said photosensitive high molecular. weight compound comprises a copolymer of at least one of said units represented by the general formulae (1) to (V) and units of a monomer copolymerizable therewith, the monomer copolymerizable therewith being from 2 to 35 percent by weight of the photosensitive high molecular weight compound.
  • the photosensitive composition as set forth in claim 13, wherein the monomer copolymerizable therewith is from 10 to 25 percent by weight of the photosensitive high molecular weight compound.
  • the photosenstiive composition as set forth in claim 1 consisting essentially of components (1), (2) and (3).
  • the photosensitive composition as set forth in claim 25 which is a copolymer of two or more materials of formulae (a) to (0).
  • the photosensitive composition as set forth in claim 25 which is a copolymer of one of materials (a) to 0) and from 10 to 25 percent by weight of another monomer copolymerizable therewith selected from the group consisting of: styrene, a-methylstyrene, acrylic acid, methacrylic acid, esters of methanol, ethanol, propanol, butanol, isobutanol, amyl alcohol, hexyl alcohol, octyl alcohol, lauryl alcohol and stearyl alcohol, acrylic acid, methacrylic acid, acrylamide, acrylonitrile, methacrylonitrile, vinyl chloride, vinyl acetate, B-hydroxyethylmethacrylate, N-methylolacrylamide, glycidyl methacrylate, ychloro-B-hydroxypropyl methacrylate, or glycerol methacrylate, based on the total weight of the polymer.
  • styrene
US00265888A 1971-06-23 1972-06-23 Photosensitive compositions comprising a photosensitive polymer and a photochromic compound Expired - Lifetime US3804628A (en)

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JP46045382A JPS5018401B1 (xx) 1971-06-23 1971-06-23

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CA (1) CA962508A (xx)
DE (1) DE2230936C3 (xx)
FR (1) FR2143173B1 (xx)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909269A (en) * 1972-07-18 1975-09-30 Western Litho Plate & Supply Lithographic plate comprising a light-sensitive polymer
US3923761A (en) * 1972-07-18 1975-12-02 Western Litho Plate & Supply Photopolymers
US3945831A (en) * 1972-12-29 1976-03-23 Fuji Photo Film Co., Ltd. Photosensitive resins containing a thienylacrylic acid ester or amide group
US3947337A (en) * 1973-05-10 1976-03-30 The Upjohn Company α,ω-Diarylpolyene photosensitizers for sulfonylazide polymers
US3964911A (en) * 1972-12-22 1976-06-22 La Cellophane Photographic reproduction processes using diazonium salts and substituted spiro[benzopyrane]
JPS5379528A (en) * 1976-12-23 1978-07-14 Fujitsu Ltd Pattern formation process
US4225661A (en) * 1978-05-10 1980-09-30 The Richardson Company Photoreactive coating compositions and photomechanical plates produced therewith
US4239848A (en) * 1979-02-26 1980-12-16 Eastman Kodak Company Photocrosslinkable carbonyl-containing polymeric composition and element with cobalt complex
US4272607A (en) * 1976-03-30 1981-06-09 Hitachi Chemical Company, Ltd. Photosensitive resin composition
US4537855A (en) * 1982-10-18 1985-08-27 Mitsubishi Chemical Industries Limited Photopolymerizable photosensitive composition
US20040259975A1 (en) * 2003-06-18 2004-12-23 Robillard Jean J. System and method for forming photobleachable ink compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3357831A (en) * 1965-06-21 1967-12-12 Harris Intertype Corp Photopolymer
US3642484A (en) * 1968-10-03 1972-02-15 Agfa Gevaert Nv Unsaturated photochromic indolino-spiropyran monomers and polymers prepared therefrom
US3652285A (en) * 1968-07-01 1972-03-28 Agfa Gevaert Nv Photochromic-photopolymerization compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3357831A (en) * 1965-06-21 1967-12-12 Harris Intertype Corp Photopolymer
US3652285A (en) * 1968-07-01 1972-03-28 Agfa Gevaert Nv Photochromic-photopolymerization compositions
US3642484A (en) * 1968-10-03 1972-02-15 Agfa Gevaert Nv Unsaturated photochromic indolino-spiropyran monomers and polymers prepared therefrom

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909269A (en) * 1972-07-18 1975-09-30 Western Litho Plate & Supply Lithographic plate comprising a light-sensitive polymer
US3923761A (en) * 1972-07-18 1975-12-02 Western Litho Plate & Supply Photopolymers
US3964911A (en) * 1972-12-22 1976-06-22 La Cellophane Photographic reproduction processes using diazonium salts and substituted spiro[benzopyrane]
US3945831A (en) * 1972-12-29 1976-03-23 Fuji Photo Film Co., Ltd. Photosensitive resins containing a thienylacrylic acid ester or amide group
US3947337A (en) * 1973-05-10 1976-03-30 The Upjohn Company α,ω-Diarylpolyene photosensitizers for sulfonylazide polymers
US4272607A (en) * 1976-03-30 1981-06-09 Hitachi Chemical Company, Ltd. Photosensitive resin composition
JPS5379528A (en) * 1976-12-23 1978-07-14 Fujitsu Ltd Pattern formation process
JPS6022346B2 (ja) * 1976-12-23 1985-06-01 富士通株式会社 フオトマスクのパタ−ン修正方法
US4225661A (en) * 1978-05-10 1980-09-30 The Richardson Company Photoreactive coating compositions and photomechanical plates produced therewith
US4239848A (en) * 1979-02-26 1980-12-16 Eastman Kodak Company Photocrosslinkable carbonyl-containing polymeric composition and element with cobalt complex
US4537855A (en) * 1982-10-18 1985-08-27 Mitsubishi Chemical Industries Limited Photopolymerizable photosensitive composition
US20040259975A1 (en) * 2003-06-18 2004-12-23 Robillard Jean J. System and method for forming photobleachable ink compositions

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CA962508A (en) 1975-02-11
DE2230936A1 (de) 1973-02-08
JPS5018401B1 (xx) 1975-06-28
DE2230936B2 (xx) 1979-11-22
FR2143173A1 (xx) 1973-02-02
DE2230936C3 (de) 1980-08-14
FR2143173B1 (xx) 1978-03-03

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