Spectral Sensitizer Containing Patents (Class 430/926)
  • Patent number: 5900346
    Abstract: The present invention relates to novel compositions that contain an activator system that comprises a photoactivator, acid generator and chain extender. Methods and articles of manufacture that comprise such compositions are also provided. In a preferred aspect, the compositions are photoimageable.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: May 4, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, Juan C. Scaiano, Gary S. Calabrese
  • Patent number: 5885745
    Abstract: Photoimageable polyquinoline compositions comprise a polyquinoline polymer, a photogenerable acid precursor and optionally a photosensitizer. The composition is prepared by dissolving the polyquinoline polymer, photogenerable acid precursor and photosensitizer in a polar solvent to form a solution, coating the solution onto a substrate and thereafter removing the solvent to form a film. The film is exposed to light through a photo mask and developed by immersion in a selective solvent to yield a photopatterned dielectric film.
    Type: Grant
    Filed: April 28, 1997
    Date of Patent: March 23, 1999
    Assignee: Hitachi Chemical Co., Ltd.
    Inventor: Matthew L. Marrocco, III
  • Patent number: 5866296
    Abstract: A photosensitive resin composition includes a polymer compound having a component of Formula (I) and a sensitizer having a cationic group in the molecule: ##STR1## (wherein X denotes a cationic species, and n is 0, 1 or 2.) The photosensitive resin composition is high in sensitivity, good in storage stability, and easy to produce, and is suitable for use in a screen printing plate, formation of black matrix or phosphor pattern of a color cathode-ray tube, a CCD or LCD color filter, a printing color proof, and various etching resists.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: February 2, 1999
    Assignee: Toyo Gosei Co., Ltd.
    Inventors: Toru Shibuya, Noriaki Tochizawa, Mitsuharu Miyazaki, Hideo Kikuchi
  • Patent number: 5858604
    Abstract: Object: A method for preparing a lithographic printing plate directly from digital image signals with the use of a presensitized lithographic printing plate comprising a support having thereon a photosensitive layer and a light-shielding layer which can be removed imagewise with laser light is provided, wherein the light-shielding layer, which can be industrially produced readily at a moderate price can be removed sufficiently during a process of development without the need of removing a masking layer at an unexposed portion and adverse effect on a photosensitive layer.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: January 12, 1999
    Assignee: Konica Corporation
    Inventors: Katsuyuki Takeda, Sota Kawakami, Katsumi Maejima, Koichi Nakatani, Shinji Matsumoto
  • Patent number: 5837586
    Abstract: Provided are 4-(alkoxyhydroxy)styryl triazine photoinitiator compounds having the formula: ##STR1## wherein n is 3 or 4, as well as photopolymerizable compositions and photographic elements containing such photoinitiator compounds. These photoinitiator compounds improve the reproduction quality of photographic elements such as lithographic printing plates since the photosensitive compositions in which they are incorporated are resistant to surface blooming.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: November 17, 1998
    Assignee: Kodak Polychrome Graphics Company, Ltd.
    Inventor: Paul A. Perron
  • Patent number: 5814431
    Abstract: A photosensitive composition comprising(a) a resin selected from the group consisting of novolak resins and polyvinylphenol resins;(b) an amino compound derivative capable of curing the resin;(c) at least one member selected from the group consisting of cyanine compounds of the following formula (I) and polymethine compounds of the following formula (II), as a compound showing absorption in a near infrared wavelength region: ##STR1## (d) a photosensitive acid-forming agent.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: September 29, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Akihisa Murata, Toshiyuki Urano, Ryuichiro Takasaki
  • Patent number: 5811218
    Abstract: An N-aryl-.alpha.-amino acid (I), which is a novel compound, is effective as a photoinitiator. The photoinitiator composition including this photoinitiator is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation. Further, a photoinitiator composition (A) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and/or an azabenzalcyclohexanone (III), or a photoinitiator composition (B) comprising an N-aryl-.alpha.-amino acid (I) or (I'), a 3-substituted coumarin (II) and a titanocene (IV), or a photoinitiator composition (C) comprising a 3-substituted coumarin (II), a titanocene (IV) and an oxime ester (V), is effective for improving photosensitive properties of photosensitive materials containing poly(amic acid) and an addition polymerizable compound used for pattern formation.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: September 22, 1998
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Makoto Kaji, Yasunori Kojima, Shigeki Katogi, Masataka Nunomura, Hideo Hagiwara, Dai Kawasaki, Mitsumasa Kojima, Hiroshi Suzuki, Hidetaka Satou
  • Patent number: 5780206
    Abstract: A resist composition for deep ultraviolet light comprising (a) one of the following resin components (i)-(iii): (i) a resin which becomes alkali-soluble by eliminating protective groups by the action of an acid, (ii) a combination of an alkali-soluble resin and a dissolution-inhibiting compound, and (iii) a combination of an alkali-soluble resin and a crosslinkable compound, (b) an acid generater, (c) a special anthracene derivative, and (d) a solvent, is suitable for forming a pattern using deep ultraviolet light, KrF excimer laser light, etc., on a highly reflective substrate having level differences due to absorption of undesirable reflected deep ultraviolet light.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: July 14, 1998
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takanori Yasuda, Akiko Katsuyama, Kazuhiro Yamashita
  • Patent number: 5763134
    Abstract: Photochemical acid progenitors in combination with dihydroperimidine squarylium dyes have been found to be particularly effective at generating acid upon irradiation with near-infrared radiation. It has been found that dihydroperimidine squarylium dyes that are particularly useful in this invention have an oxidation potential greater than about 0.5 V relative to SCE as measured in dichloromethane.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: June 9, 1998
    Assignee: Imation Corp
    Inventors: Stanley C. Busman, Richard J. Ellis, Jeanne E. Haubrich, William D. Ramsden, Tran Van Thien, Gregory D. Cuny
  • Patent number: 5738974
    Abstract: A photopolymerizable composition comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, wherein the photopolymerization initiator system comprises:(a) a titanocene compound, and(b) at least one coumarin compound of the following formula (I): ##STR1## wherein (i) each of R.sup.1, R.sup.2 and R.sup.5 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, each of R.sup.3 and R.sup.4 is an alkyl group, provided that at least one of R.sup.3 and R.sup.4 is a C.sub.4-16 alkyl group, or (ii) R.sup.1 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, and at least one set of R.sup.2 and R.sup.3, and R.sup.4 and R.sup.5, is connected to form an alkylene group substituted by a lower alkyl group, provided that when they do not form the connecting group, each of R.sup.2 and R.sup.5 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, and each of R.sup.3 and R.sup.
    Type: Grant
    Filed: August 29, 1995
    Date of Patent: April 14, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Toshiyuki Urano, Akihisa Murata
  • Patent number: 5731123
    Abstract: Provided is a positive image forming composition which comprises (a) a compound generating an acid when exposed to light or heat and (b) a sulfonimide compound represented by the following formula (I):L.sub.1 --(SO.sub.2 --NR.sub.2 --SO.sub.2 --R.sub.1).sub.n (I)wherein n is an integer from 1 to 6; R.sub.1 is an aromatic group or an alkyl group; L.sub.1 is an aromatic group or an alkyl group in the case of n=1, while it is a polyvalent organic linkage group in the case of n=2-6; and R.sub.2 is an alkoxymethyl group, an arylmethyl group, or an alicyclic alkyl group; or a polymer containing in side chains constitutional units represented by the following formula (I'):--L--SO.sub.2 --NR.sup.2 --SO.sub.2 --R.sup.1 (I')wherein R.sup.1 has the same meaning as R.sub.1 in formula (I); L is a polyvalent organic group for connecting the constitutional unit of formula (I') to the polymer skeleton; and R.sup.2 has the same meaning as R.sub.2 in formula (I).
    Type: Grant
    Filed: January 31, 1997
    Date of Patent: March 24, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Kazuya Uenishi
  • Patent number: 5725992
    Abstract: A photosensitive material for the production of color proofing films for multicolor printing, having(A) a transparent, flexible film support,(B) a photopolymerizable layer which contains(B1) a polymeric binder,(B2) a free-radical-polymerizable compound,(B3) a substituted bistrihalomethyl-s-triazine having an absorption maximum in the range from 300 to 380 nm and an absorbance of greater than 11,000 at the absorption maximum, and an absorbance of less than 1400 at 400 nm and above, as photoinitiator, and(B4) a dye or a colored pigment in a primary color of multicolor printing, and(C) a thermoplastic adhesive layer on the photo-sensitive layer.The material is processed by lamination onto an image-receiving material, exposure of the material and peeling apart of film support and image-receiving material, leaving the unexposed layer areas on the image-receiving material together with the adhesive layer. To produce a multicolored image, these steps are repeated with at least one further single-color sheet.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: March 10, 1998
    Assignee: Agfa-Gevaert AG
    Inventors: Stephan J. W. Platzer, Wojciech A. Wilczak, Gerhard Buhr, Dieter Mohr
  • Patent number: 5695910
    Abstract: A resist composition for deep ultraviolet light comprising (a) one of the following resin components (i)-(iii): (i) a resin which becomes alkali-soluble by eliminating protective groups by the action of an acid, (ii) a combination of an alkali-soluble resin and a dissolution-inhibiting compound, and (iii) a combination of an alkali-soluble resin and a crosslinkable compound, (b) an acid generater, (c) a special anthracene derivative, and (d) a solvent, is suitable for forming a pattern using deep ultraviolet light, KrF excimer laser light, etc., on a highly reflective substrate having level differences due to absorption of undesirable reflected deep ultraviolet light.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: December 9, 1997
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electrical Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takanori Yasuda, Akiko Katsuyama, Kazuhiro Yamashita
  • Patent number: 5686220
    Abstract: A photo-curing composition including an image forming material, an ethylenically unsaturated monomer which is curable by polymerization thereof, a polymerization initiator which initiates the polymerization of the monomer, and two or more photosensitizers each of which absorbs a light and thereby causes the polymerization initiator to initiate the polymerization of the monomer, the photosensitizers having different maximum absorption wavelengths, respectively. A photosensitive capsule including a core material including the photo-curing composition, and a shell material within which the core material is encapsulated.
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: November 11, 1997
    Assignee: Brother Kogyo Kabushiki Kaisha
    Inventor: Masashi Tsuda
  • Patent number: 5663037
    Abstract: A radiation-sensitive composition especially adapted to prepare a lithographic printing plate that is sensitive to both ultraviolet and infrared radiation and capable of functioning in either a positive-working or negative-working manner is comprised of (1) a resole resin, (2) a novolac resin, (3) a haloalkyl-substituted s-triazine and (4) an infrared absorber. The solubility of the composition in aqueous alkaline developing solution is both reduced in exposed areas and increased in unexposed areas by the steps of imagewise exposure to activating radiation and heating.
    Type: Grant
    Filed: September 26, 1995
    Date of Patent: September 2, 1997
    Assignee: Eastman Kodak Company
    Inventors: Neil Frederick Haley, Steven Leo Corbiere
  • Patent number: 5609992
    Abstract: A photopolymerizable composition is disclosed, comprising (i) a compound having at least one addition-polymerizable, ethylenically unsaturated bond; (ii) a compound represented by formula (IA) or (IB): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a hydroxyl group, a substituted oxy group, a mercapto group, a substituted thio group, an amino group, a substituted amino group, a substituted carbonyl group, a sulfo group, a sulfonato group, a substituted sulfinyl group, a substituted sulfonyl group, a phosphono group, a substituted phosphono group, a phosphonato group, a substituted phosphonato group, a cyano group or a nitro group or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.9 and R.sup.10, R.sup.10 and R.sup.11 or R.sup.11 and R.sup.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tadahiro Sorori, Yasuo Okamoto, Syunichi Kondo, Hiromichi Kurita
  • Patent number: 5607817
    Abstract: A photopolymerizable composition comprising an addition polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator system, wherein the photopolymerization initiator system comprises:(a) a sensitizer of the formula (I) ##STR1## wherein -A is ##STR2## wherein each of R.sup.1 and R.sup.2 is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, each of R.sup.3 and R.sup.4 is an alkyl group which may have substituents, each of R.sup.5 to R.sup.8 is a hydrogen atom, an alkyl group or an alkoxy group, or R.sup.3 and R.sup.4, R.sup.3 and R.sup.5 and/or R.sup.4 and R.sup.6 bond to each other to form a ring structure, and n is 0, 1 or 2; and each of X.sup.1 and X.sup.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Masaaki Tsuchiyama, Toshiyuki Urano
  • Patent number: 5561029
    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 the following general formula [I]: ##STR1## wherein R.sub.1 is either OR.sub.4 or NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 may or may not be identical with each other, either R.sub.5 or R.sub.6 may represent hydrogen, and wherein R.sub.4 and at least one of R.sub.5 and R.sub.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: October 1, 1996
    Assignee: Polaroid Corporation
    Inventors: Maurice J. Fitzgerald, Frederick R. Kearney, Rong-Chang Liang, William C. Schwarzel, Donna J. Guarrera, John M. Hardin, John C. Warner
  • Patent number: 5466557
    Abstract: A radiation-sensitive composition especially adapted to prepare a lithographic printing plate that is sensitive to both ultraviolet and infrared radiation and capable of functioning in either a positive-working or negative-working manner is comprised of (1) a resole resin, (2) a novolac resin, (3) a latent Bronsted acid, (4) an infrared absorber, and (5) terephthalaldehyde. The solubility of the composition in aqueous alkaline developing solution is both reduced in exposed areas and increased in unexposed areas by the steps of imagewise exposure to activating radiation and heating.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Steven L. Corbiere
  • Patent number: 5455143
    Abstract: Aminoketone-substituted coumarin sensitizers having quaternary amine substituents are described which have very high photosensitivity, and are useful in moderate pH aqueous-developable printing plates. The aminoketone-substituted coumarin sensitizers are described by the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 each represent hydrogen; or at least one of R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together represent an alkylene group having 2 to 4 carbon atoms,R.sub.5 represents an alkyl group having 1 to 6 carbon atoms or H,R.sub.6 represents an alkylene group having 1 to 16 carbon atoms, an oxyalkylene group having form 1 to 16 carbon atoms, or a poly(oxyalkylene) group in which said alkylene group has 2 to 4 carbon atoms and the number of oxygen atoms is a positive integer less than or equal to four,R.sub.7, R.sub.8, and R.sub.9 each independently represent an alkyl group having 1 to 6 carbon atoms, or any two of R.sub.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: October 3, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: M. Zaki Ali
  • Patent number: 5415976
    Abstract: Aminoketone-substituted coumarin sensitizers having tethered tertiary amino groups are described which have extremely good photosensitivity. The sensitizers of the instant invention have the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent an alkyl group having 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 each represent hydrogen; or at least one of R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together represent an alkylene group having 2 to 4 carbon atoms,R.sub.5 represents an alkyl group having 1 to 6 carbon atoms or H,R.sub.6 represents an alkylene group having 1 to 6 carbon atoms, andR.sub.7 and R.sub.8 each independently represent an alkyl group having 1 to 6 carbon atoms, both of R.sub.7 and R.sub.8 taken together represent an alkylene group having 4 to 6 carbon atoms, or R.sub.5 or R.sub.6 taken together with R.sub.7 or R.sub.8 represent a five, six, or seven membered heterocyclic ring group.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: M. Zaki Ali
  • Patent number: 5391465
    Abstract: A method is provided for using selected photoactive compounds in acid hardening photoresists to produce thermally stable, high resolution images with near ultraviolet exposing radiation. These photoactive compounds can be used as photosensitizers for halogen-containing photoacid generators which by themselves do not otherwise generate sufficient acid upon exposure to near ultraviolet radiation to catalyze the crosslinking of acid hardening resins. The photoactive compounds are selected from the group consisting of phenothiazine, derivatives of phenothiazine, and phenoxazine.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: February 21, 1995
    Assignee: Rohm and Haas Company
    Inventor: Wayne E. Feely
  • Patent number: 5372907
    Abstract: A radiation-sensitive composition especially adapted to prepare a lithographic printing plate that is sensitive to both ultraviolet and infrared radiation and capable of functioning in either a positive-working or negative-working manner is comprised of (1) a resole resin, (2) a novolac resin, (3) a latent Bronsted acid and (4) an infrared absorber. The solubility of the composition in aqueous alkaline developing solution is both reduced in exposed areas and increased in unexposed areas by the steps of imagewise exposure to activating radiation and heating.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: December 13, 1994
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Steven L. Corbiere
  • Patent number: 5372908
    Abstract: A photosensitive composition comprises a polysilane having a repeating unit represented by formula (1) and a compound which generates an acid upon exposure to light: ##STR1## wherein each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a substituted or nonsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or nonsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or nonsubstituted aralkyl group having 7 to 22 carbon atoms. This photosensitive composition exhibits a high-sensitivity, and can be formed into a polysilane film pattern having a high-resolution, when it is subjected to exposure to Deep UV light, an EB, an X-ray, or the like, hard baking, and development under appropriate conditions. When an aromatic ring substituted by a hydroxyl group, a substituted or nonsubstituted alkoxyl group, or a substituted or nonsubstituted siloxyl group is introduced in one of side chains R.sup.1 and R.sup.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: December 13, 1994
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuji Hayase, Yoshihiko Nakano, Yukihiro Mikogami
  • Patent number: 5372915
    Abstract: A radiation-sensitive composition especially adapted to prepare a lithographic printing plate that is sensitive to both ultraviolet and infrared radiation and capable of functioning in either a positive-working or negative-working manner is comprised of (1) a resole resin, (2) a novolac resin, (3) a latent Bronsted acid and (4) an infrared absorber. The solubility of the composition in aqueous alkaline developing solution is both reduced in exposed areas and increased in unexposed areas by the steps of imagewise exposure to activating radiation and heating.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: December 13, 1994
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Steven L. Corbiere
  • Patent number: 5354644
    Abstract: A photoresist composition which includes a sensitizing compound, a resin and, as a light absorber, a styryl compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.11 are the same or different and a hydrogen atom, an optionally substituted alkyl, alkenyl or aralkyl group or R.sub.1 and R.sub.2 may form a ring together with the nitrogen atom to which they are bonded, which ring may include at least one hetero atom in addition to said nitrogen atom; R.sub.10 is an optionally substituted alkylene group; R.sub.3 is --OH, --OCOR.sub.5 or --OSi(R.sub.5).sub.3 in which R.sup.5 is an alkyl group; R.sub.12 and R.sub.13 are independently a hydrogen atom, an optionally substituted lower alkyl or alkoxy group, an amide group or a halogen atom; X, Y, W and Z are the same or different and an electron attracting group, and n is a number of 2-15.
    Type: Grant
    Filed: September 1, 1992
    Date of Patent: October 11, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takanori Yamamoto, Shinji Konishi, Ryotaro Hanawa, Akihiro Furuta, Takeshi Hioki, Jun Tomioka
  • Patent number: 5346801
    Abstract: An image forming process of an image forming material comprising a support and provided thereon, a photosensitive layer and a covering layer in that order comprises imagewise exposing the material by laser beam scanning, and peeling the covering film from the exposed material to form an image on the support or on the covering film, wherein said photosensitive layer contains a colorant, an addition-polymerizable or cross-linkable compound and a salt of a cationic dye with a borate anion represented by the following Formula (1):Formula (1) ##STR1##
    Type: Grant
    Filed: March 18, 1993
    Date of Patent: September 13, 1994
    Assignee: Konica Corporation
    Inventors: Hiroshi Watanabe, Tatsuichi Maehashi, Koichi Nakatani, Katsunori Kato, Tawara Komamura
  • Patent number: 5346805
    Abstract: A photopolymerizable composition comprises a polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator, wherein the photopolymerization initiator comprises an onium compound and an acridine derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an unsubstituted or substituted phenyl, alkyl or alkoxy group. The composition has high sensitivity to actinic rays over a wide range of wavelength extending from ultraviolet to visible region and thus can be used for preparing a lithographic printing plate, a resin-letterpress plate, a resist or photomask for making a printed board, a monochromatic and colored sheet for transfer or color-development and a color-developing sheet.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: September 13, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Syunichi Kondo, Akira Umehara
  • Patent number: 5328803
    Abstract: A photopolymerizable composition developable with an alkali aqueous solution which comprises a carboxyl group-containing high polymer binder, a photopolymerizable monomer, a photopolymerization initiator system and a compound of a specific structure is disclosed. The photopolymerizable composition shows a good keeping stability in a state of lamination on a metal board and thus is highly useful in the production of, for example, dry films for print basic boards, photoresists, photomasks, lithograph boards and resin relief boards.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: July 12, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Sadao Fujikura, Masayuki Iwasaki, Yuichi Wakata
  • Patent number: 5320931
    Abstract: A positive working light-sensitive composition comprising (a) a compound capable of generating acids through irradiation of actinic rays or radiant rays, (b) an organic base and (c) an alkali-soluble polymer. The composition is highly sensitive to light in wider wavelength region and highly resistant to aging. It can easily be produced and can hence be easily available.
    Type: Grant
    Filed: July 17, 1991
    Date of Patent: June 14, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Umehara, Syunichi Kondo, Tsuguo Yamaoka
  • Patent number: 5286603
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerisable composition. The composition comprises a polymerisable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodised aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Vickers PLC
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5272042
    Abstract: Disclosed is a positive photoresist. The photoresist has as its polymeric component a substantially water and base insoluble, photolabile polymer. The photoresist further includes a photo acid generator that is capable of forming a strong acid. This photo acid generator may be a sulfonate ester derived from a N-hydroxyamide, or a N-hydroxyimide. Finally, the photoresist composition includes an appropriate photosensitizer.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: December 21, 1993
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, William R. Brunsvold, Burton J. Carpenter, William D. Hinsberg, Joseph LaTorre, Michael G. McMaster, Melvin W. Montgomery, Wayne M. Moreau, Logan L. Simpson, Robert J. Tweig, Gregory M. Wallraff
  • Patent number: 5250384
    Abstract: A novel light-sensitive heat-sensitive composition is disclosed, comprising a photohardenable composition, a dye which discolors upon reacting with a base, and a base precursor. A novel light-sensitive heat-sensitive recording material is also disclosed, comprising a support having provided thereon the above described light-sensitive heat-sensitive composition. In a preferred embodiment, the dye is a spectral sensitizing dye for the photohardenable composition. Furthermore, a novel image formation process is disclosed, comprising the steps of: (a) imagewise exposing the light-sensitive heat-sensitive recording material to light to cure the exposed portions of the recording material; and (b) uniformly heating the imagewise exposed recording material to discolor the dye in the unexposed portions thereof.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: October 5, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Jun Yamaguchi, Sadao Ishige, Takekatsu Sugiyama
  • Patent number: 5236808
    Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photoinitiator system comprises a sensitizer which is a compound of the structure I: ##STR1## wherein R.sub.2 and R.sub.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: August 17, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5217846
    Abstract: This invention relates to photopolymerizable compositions containing initiator systems that absorb in the longer wavelength region of the visible spectrum. Photopolymerizable compositions containing selected photodissociable initiators in combination with photobleachable sensitizers are disclosed.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: June 8, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5212046
    Abstract: A photoacid-generating photoresist composition sensitized with an aromatic, multi-ring, heterocylcic nitrogen containing sensitizer, preferably a ring extended phenothiazine derivative. The use of the sensitizer permits exposure of photoresists to near UV irradiation where such photoresists have heretofore been exposed to deep UV irradiation. The invention is especially useful for acid hardening photoresist systems.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: May 18, 1993
    Assignee: Shipley Company Inc.
    Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
  • Patent number: 5208135
    Abstract: Compounds having a utility as photosensitive dyes in photocurable polymer based imaging systems having a nucleus of general formula (I): ##STR1## wherein: n is 1 or 2,Y is selected from the group consisting of 0 and ##STR2## Z is selected from the group consisting of 0.sup..crclbar. and ##STR3## M.sup..sym. is a cation.
    Type: Grant
    Filed: February 11, 1991
    Date of Patent: May 4, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ranjan C. Patel, Tran V. Thien, David Warner
  • Patent number: 5202221
    Abstract: The present invention relates to a light-sensitive composition comprising (a) a photo-crosslinkable polymer having a maleimido group at a side chain and (b) a sensitizer such as the following compounds: ##STR1## The present invention provides a light-sensitive composition having very high sensitivity; providing excellent images during only a short exposure time; and being sensitive to light of long wave length.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: April 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
  • Patent number: 5200292
    Abstract: A light-sensitive composition is provided comprising (a) an aromatic diazo compound and (b) a cationic dye/borate anion complex.In a preferred embodiment, the cationic dye/anionic borate dye complex is represented by the general formula (I): ##STR1## wherein D.sup.+ represents a cationic dye; and R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, each represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted alicyclic group, or an unsubstituted or substituted heterocyclic group.The aromatic diazo compound can be a nonionic diazo compound.The light-sensitive compound can further comprise a radical-polymerizable unsaturated compound.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: April 6, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiaki Shinozaki, Junichi Fujimori
  • Patent number: 5166041
    Abstract: The present invention relates to a near infrared ray-decolorizable recording material comprising a near infrared ray-absorbing cationic dye-borate anion complex having the formula (I): ##STR1## wherein D.sup.+ represents a cationic dye having absorptions in the near infrared region; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 independently represent an alkyl, aryl, alkaryl, allyl, aralkyl, alkenyl, alkynyl, silyl, alicyclic, or saturated or unsaturated heterocyclic group, substituted alkyl, substituted aryl, substituted alkaryl, substituted allyl, substituted aralkyl, substituted alkenyl, substituted alkynyl, or substituted silyl, with the proviso that at least one of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 represents an alkyl group having 1 to 8 carbon atoms.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: November 24, 1992
    Assignee: Showa Denko K.K.
    Inventors: Katsumi Murofushi, Yoshikazu Hosoda, Yoke Ai Gan, Kunio Kondo
  • Patent number: 5141841
    Abstract: A radiation-sensitive compound has the general formula ##STR1## wherein A represents the ring members required to complete a 5- or 6-membered heterocyclic ring which may optionally be fused to an optionally substituted aromatic nucleus,B represents H, acyl, aroyl, heterocyclyl carbonyl or ##STR2## R represents an optionally substituted alkyl group, E and G, which may be the same or different, each represents H or CH.sub.p X.sub.3-p,J and K, which may be the same or different, each represents an aryl or heterocyclic group, which may optionally include a substituent additional to E or G,X represents Cl or Br, and m,n and p, which may be the same or different, each represents an integer equal to 0, 1 or 2.The compound can be used to form radiation sensitive compositions for the production of radiation sensitive plates in lithographic printing plate manufacture.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Vickers PLC
    Inventor: John R. Wade
  • Patent number: 5130227
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerizable composition. The composition comprises a polymerizable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodized aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: July 14, 1992
    Assignee: Vickers Plc
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5114832
    Abstract: A photopolymerizable mixture is described, which contains a polymeric binder; an acrylate or alkacrylate of a polyhydric alcohol possessing at least one photooxidizable group; a compound or a combination of compounds being capable of initiating the polymerization of the ester under the action of light in the spectral region of 450 nm to 650 nm; and at least one compound which absorbs light in the region below 450 nm or which upon exposure forms a compound absorbing light in said region, whereby the optical density of the exposed mixture in this region is at least 2.0 at a layer thickness of 2 .mu.m. The mixture is useful for the production of masters or intermediate masters for reprographic layers being sensitive to light in the UV region, exposure of the mixture itself being performed with visible light.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: May 19, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Zertani, Dieter Mohr, Klaus Rode, Werner Frass, Klaus Joerg
  • Patent number: 5112721
    Abstract: Combinations of selected photosensitizers produce unexpected increases in the both the photospeed of, and the resolution obtainable from, photopolymerizable compositions. The combinations contain one photosensitizer, known as the sensitizer, and a second photosensitizer, known as the co-sensitizer. The co-sensitizer has an absorbance maximum at a longer wavelength than the sensitizer and is generally present a much lower concentration than the sensitizer.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: May 12, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: August D. Kuchta
  • Patent number: 5102775
    Abstract: A composition for visible light sensitive electrodeposition coating which comprises (A) a photocurable resin having light sensitive groups capable of being crosslinked or polymerized by light irradiation and ionic groups, (B) a sensitizer which is excited by absorption of visible light and has a property to interact with the resin (A), (C) a water-insoluble polymerization initiator, and optionally, (D) at least one specific nitrogen-containing compound; and an image-forming method which comprises (i) coating the surface of a conductor by electrodeposition with the aforesaid composition, (ii) exposing the resulting film by electrodeposition by partially irradiating the film with visible light, and then (iii) contacting the resulting film with a developing solution to remove the unexposed areas.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: April 7, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Motoko Okuhara, Ichiro Yoshihara, Yasuo Doi, Takao Yamamoto, Kenji Seko, Yutaka Yoshikawa, Naozumi Iwasawa
  • Patent number: 5066573
    Abstract: A silver halide color photographic material is described, comprising a support having thereon at least one of a silver halide emulsion layer and other hydrophilic colloid layer, wherein the silver halide emulsion layer or a hydrophilic colloid layer contains at least one compound represented by formula (II): ##STR1## wherein R.sub.2 represents a hydrogen atom or a group that can be substituted, Y.sub.1 represents ##STR2## R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be the same or different, each represents a hydrogen atom or a group that can be substituted; X.sub.1 represents a divalent linking group containing a hetero atom connected to the carbon atom; m is 0 or 1; A represents a bleach accelerating agent moiety represented by ##STR3## wherein R.sub.9, L, X.sub.2 R.sub.10 B, l.sub.1 and L.sub.2 are defined in the specification.The compound represented by formula (II) is a bleach accelerating agent having an active group of adsorptive group.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: November 19, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tetunori Matushita, Morio Yagihara, Kei Sakanoue
  • Patent number: 5064747
    Abstract: A light-sensitive composition comprises a photo-crosslinkable polymer having a photo-dimerizable unsaturated bond and a sensitizer represented by the following general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted allyl group, provided that R.sub.1 and R.sub.2 may form a ring together with the carbon atoms to which they are attached; n represents 0, 1 or 2; and G.sub.1 and G.sub.2 each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted arylcarbonyl group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group or a fluoroalkylsulfonyl group, provided that G.sub.1 and G.sub.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: November 12, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
  • Patent number: 5059512
    Abstract: An ultraviolet light sensitive photoinitiator composition that includes at least one anthracene derivative represented by the formula: ##STR1## wherein X is CH.dbd.CH.sub.2 or --(--CH.sub.2 --)--.sub.n O--(--R) with R being H or ##STR2## wherein each R.sup.I, R.sup.II and R.sup.III individually is selected from the group of alkyl, alkenyl, aryl, ##STR3## wherein each R.sup.IV, R.sup.V and R.sup.VI individually is selected from the group of alkyl, alkenyl and aryl; wherein m is an integer of 0 to 4, p is an integer of 0 to 4; and is n being 1 to 2; and onium salt; and an organic solvent. The composition is used for cationic polymerization of cationic polymerizable materials including in the formation of a pattern of a photoresist. Also certain novel epoxy-functionalized organosilicons are provided that are sensitive to radiation including E-beam radiation and exhibit resistance to oxygen reactive ion etching.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: October 22, 1991
    Assignee: International Business Machines Corporation
    Inventors: Edward D. Babich, Jeffrey D. Gelorme, Michael Hatzakis, Jane M. Shaw, Kevin J. Stewart, David F. Witman
  • Patent number: 5057398
    Abstract: A photopolymerizable composition that contains a polymeric binder, a polymerizable compound and photoinitiator combination comprising an N-heterocyclic compound and a halogen compound corresponding to one of the folowing formulas I and II ##STR1## in which X.sup.1 stands for chlorine or bromine,X.sup.2 and X.sup.3 are identical or different and denote X.sup.1, hydrogen or alkyl groups,Y and Z are identical or different and denote X.sup.1, hydrogen, CN or (A).sub.n --(B).sub.n --D,A is a phenylene group,n is 0 or 1,B is CO or SO.sub.2,D is R, OR, NHR, NH.sub.2, NR.sub.2 or CX.sup.1 X.sup.2 X.sup.3,R is an alkyl, cycloalkyl, aryl or heteroyl radical,W is a five or six-membered heterocyclic ring having from 1 to 3 heteroatoms, which optionally carries substituents and optionally a fused aromatic ring, andm is 1 or 2,is distinguished by an improved light sensitivity.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: October 15, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Dieter Frommeld, Hansjoerg Vollmann
  • Patent number: 5049481
    Abstract: A photopolymerizable composition comprising (i) a polymerizable compound having an addition polymerizable unsaturated bond, (ii) a compound represented by formula (Ia): ##STR1## a compound represented by formula (Ib): ##STR2## or a compound represented by formula (Ic): ##STR3## wherein A represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, an alkyl- or aryl-substituted nitrogen atom, or a dialkyl-substituted carbon atom; Y.sup.1 represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, an acyl group, an alkoxycarbonyl group, or a substituted alkoxycarbonyl group; R.sup.1 and R.sup.2 each represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, or an alkyl group having from 1 to 18 carbon atoms which is substituted with R.sup.3 O--, ##STR4## or a halogen atom (i.e., F, Cl, Br, and I), wherein R.sup.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: September 17, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuo Okamoto, Tadahiro Sorori