Polymeric Mixture Patents (Class 430/176)
  • Patent number: 5393637
    Abstract: Disclosed is a photosensitive composition used for offset printing, which provides an offset printing plate with excellent durability and developability. The photosensitive composition comprises:(I) a film-forming binder resin,(II) a photosensitive substance, and(III) a microgel having a particle size of 0.01 to2.0 .mu. prepared by emulsion polymerization using a polymeric emulsifier having an Sp value of 9 to 16.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: February 28, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Yoshifumi Ichinose, Seiji Arimatsu, Katsuji Konishi, Takakazu Hase
  • Patent number: 5389491
    Abstract: A negative working resist composition comprising (a) an alkali-soluble resin, (b) an aromatic compound having at least two groups of the formula: --OCH.sub.2 OR.sup.1 wherein R.sup.1 is alkyl or aralkyl, (c) a photoacid generator, and (d) a solvent, can form fine patterns with high resolution when exposed to deep UV, KrF excimer laser light, etc. due to high light transmittance and high sensitivity.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: February 14, 1995
    Assignees: Matsushita Electric Industrial Co., Ltd., Wako Pure Chemical Industries, Ltd.
    Inventors: Yoshiyuki Tani, Masayuki Endo, Fumiyoshi Urano, Takanori Yasuda
  • Patent number: 5382495
    Abstract: It has surprisingly been found that a protective coating composition for diazo-containing materials can be prepared from a cellulose ester, a hydroxylated resin, a crosslinking agent, microcrystalline silica and an acid catalyst. The coating compositions of the invention provide improved protection for diazo-containing materials from physical and chemical damage. The protective coating compositions of the invention are particularly effective for protecting the diazo-containing materials from chemical attack from solvents. The invention further relates to photographic elements and phototools provided with the protective coating composition and a method for providing the coating composition.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: January 17, 1995
    Assignee: Rexham Graphics, Inc.
    Inventors: Thomas C. Niziolek, George Hodgins, Marie B. Ray
  • Patent number: 5378585
    Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.
    Type: Grant
    Filed: October 13, 1993
    Date of Patent: January 3, 1995
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • 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: 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: 5370965
    Abstract: A positive-working light-sensitive composition comprises a diazonium salt represented by the following general formula (I) and an alkali-soluble polymer: ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group having 3 to 18 carbon atoms; R.sup.2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted phenoxy group or a halogen atom; A represents an organic group; X.sup.-- represents a counterion or an anion; n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 3, provided that the sum of n and m is equal to 4. The positive-working light-sensitive composition has high sensitivity and can ensure the formation of clear images.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: December 6, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shunichi Kondo, Mitsumasa Tsuchiya, Sadao Ishige, Takekatsu Sugiyama, Toshifumi Inno, Yoshimasa Aotani
  • Patent number: 5368976
    Abstract: The present invention provides a pigment dispersed color-filter composition containing a binder polymer such as an alkali-soluble block copolymer; a radiation-sensitive compound; and a pigment. The pigment-dispersed color-filter composition which further contains an organic medium, or an organic medium and a carboxylic acid is also provided.
    Type: Grant
    Filed: March 24, 1993
    Date of Patent: November 29, 1994
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yusuke Tajima, Nobuo Bessho, Fumitake Takinishi, Yasuaki Yokoyama, Hideaki Masuko
  • Patent number: 5364738
    Abstract: A positive-working light-sensitive composition whose solubility in a developer is increased by irradiation of light, which comprises:(a) a vinyl ether compound having at least one group represented by the following formula (A); ##STR1## wherein R.sup.3 represents a linear or branched alkylene group having 1 to 10 carbon atoms and n represents an integer of 0 or 1;(b) a compound capable of being decomposed by irradiation of an actinic light ray or a radiant ray and releasing an acid; and(c) an alkali-soluble polymer, the light-sensitive composition having high sensitivity to light and permitting the use of light of a wide wavelength range.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: November 15, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shunichi Kondo, Akira Umehara, Yoshimasa Aotani, Tsuguo Yamaoka
  • Patent number: 5362607
    Abstract: A method for preparing a positive photoresist substrate composite is provided which can be used in the presence or absence of atmospheric moisture. There is used a major amount of a commercially available resin, such as a novolak, a dissolution inhibitor with thermally labile t-butyl ether or ester groups, and an aryl onium salt.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: November 8, 1994
    Assignee: MicroSi, Inc.
    Inventors: James V. Crivello, Michael J. O'Brien, Julia L. Lee
  • Patent number: 5350660
    Abstract: A resist material comprising (a) a polymer having a monomer unit having a special functional group, a monomer unit having a phenolic hydroxyl group, and if necessary a third monomer unit, (b) a photoacid generator, and (c) a solvent can provide a resist film excellent in heat resistance and adhesiveness to a substrate when exposed to light with 300 nm or less such as deep UV light, KrF excimer laser light, etc., and is suitable for forming ultrafine patterns.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: September 27, 1994
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono
  • Patent number: 5348834
    Abstract: This invention relates to water developable, negative working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process. The invention provides both overlay and transfer type proofing sheets which have good fingerprint resistance.
    Type: Grant
    Filed: February 2, 1993
    Date of Patent: September 20, 1994
    Assignee: Hoechst Celanese Corporation
    Inventor: Stanley F. Wanat
  • Patent number: 5346806
    Abstract: Ligomeric sulfonic acid derivatives having repeating units of the formula I ##STR1## in which R.sup.1 is an alkyl, haloalkyl or aryl radical,R.sup.2 is a hydrogen atom, an alkyl, alkenyl or aryl radical or the group (R.sup.1 --SO.sub.2 --O--).sub.n X--,R.sup.3 is a cycloalkylenedialkyl, cycloalkenylenedialkyl, arylenedialkyl, heteroarylenedialkyl group, alkylene, alkenylene, alkynylene, cycloalkylene or arylene group,X is an alkylene, cycloalkylene or arylene group Y is O, S, CO, CO--O, SO.sub.2, SO.sub.2 --O, NR.sup.4, CO--NH, O--CO--NR.sup.5, NH--CO--NR.sup.5 or NR.sup.5 --CO--O,Z is O, CO--NR.sup.6, O--CO--NR.sup.6 or NH--CO--NR.sup.6,R.sup.4 is an acyl radical,R.sup.5 is a hydrogen atom or an alkyl-, cycloalkyl, alkenyl, alkynyl or aryl radical,R.sup.6 is an alkyl, cycloalkyl, alkenyl, alkynyl or aryl radical,k is 0, 1, 2, 3 or 4,m is an integer greater than 1 andn is 1, 2 or 3,generate sulfonic acids under irradiation and are cleavable by the latter.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: September 13, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Charlotte Eckes
  • Patent number: 5346804
    Abstract: A radiation-sensitive mixture which contains compounds of the formula I which generate under irradiation sulfonic acids and are cleavable by the latter ##STR1## in which R.sup.1 is an unsubstituted or substituted alkyl, fluorinated alkyl, perfluoroalkyl or aryl radical,R.sup.2 is a hydrogen atom, an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical, (R.sup.1 --SO.sub.2 --O--).sub.n X--, or R.sub.3 O--,R.sup.3 and R.sup.4 are identical or different and are unsubstituted or substituted alkyl, cycloalkylalkyl, cycloalkenylalkyl or aralkyl radicals, in which 1 to 3 aliphatic CH.sub.2 or CH groups are optionally replaced by one or more of NR.sup.5, O, S, CO, CO--O, CO--NH, O--CO--NH, CO--NH--CO, NH--CO--NH, SO.sub.2, SO.sub.2 --O or SO.sub.2 --NH, or unsubstituted or substituted alkenyl, alkynyl, cycloalkyl or cycloalkenyl radicals, or R.sup.3 and R.sup.4 are mutually linked to form an unsubstituted or substituted heterocyclic ring,R.sup.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: September 13, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Geog Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Charlotte Eckes
  • Patent number: 5344739
    Abstract: A photosensitive diazo resin-containing photosensitive resin composition for lithographic printing comprising a sensitizing dye having an anion group in a molecule as a counter ion of a diazonium group.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: September 6, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Osamu Nanba, Edward Lam
  • Patent number: 5342727
    Abstract: A copolymer of (a) an unsubstituted 4-hydroxystyrene monomer and (b) a substituted 4-hydroxystyrene monomer of the formula ##STR1## wherein A, B, C, and D are independently H or C.sub.1 to C.sub.4 alkyl and wherein at least one of B and D is C.sub.1 to C.sub.4 alkyl; and wherein said copolymer has a molecular weight of from about 800 to about 100,000; and wherein the mol ratio of monomer (a) to monomer (b) ranges from about 3:1 to about 1:3.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: August 30, 1994
    Assignees: Hoechst Celanese Corp., IBM Corp.
    Inventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
  • Patent number: 5340685
    Abstract: A light-sensitive composition comprises a light-sensitive diazo resin, a polymer binder and a fluorine atom-containing surfactant, wherein the polymer binder is a polyurethane resin having acidic hydrogen atom-containing substituents and comprising structural units derived from a diol represented by the following general formula (I); and the fluorine atom-containing surfactant is a copolymer of (i) an acrylate or methacrylate having a fluoroaliphatic group which has a carbon atom number of 3 to 20 and a fluorine atom content of not less than 30% by weight and in which at least three terminal carbon atoms are completely fluorinated, with (ii) poly(oxyalkylene) acrylate or poly(oxyalkylene)methacrylate, the copolymer containing the fluoroaliphatic group-containing acrylate or methacrylate units in an amount ranging from 35 to 50% by weight on the basis of the weight of the copolymer and the copolymer having has a molecular weight ranging from 20,000 to 100,000:HO--(CH.sub.2 CH.sub.2 O).sub.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiyuki Sekiya
  • Patent number: 5340699
    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: August 23, 1994
    Assignee: Eastman Kodak Company
    Inventors: Neil F. Haley, Steven L. Corbiere
  • Patent number: 5338640
    Abstract: A novel siloxane polymer having at least 1 mol % of a structural unit derived from a cyclic heat addition product between a diene compound of formula (I) or (II) and an olefin or acetylene compound of formula (III), (IV) or (V): ##STR1## and a positive working light-sensitive composition comprising the siloxane polymer.
    Type: Grant
    Filed: August 28, 1992
    Date of Patent: August 16, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuyoshi Mizutani
  • Patent number: 5332648
    Abstract: A photosensitive composition comprising: an acid-decomposable compound having at least one substituent which is decomposed by an acid, forming a product which reacts with alkali solution and forms --COO.sup.- or --SO.sub.3.sup.- ; and a compound which generates an acid when exposed to a chemical radiation. If necessary, the composition further comprises an alkali-soluble polymer. The acid-decomposable compound is one which is represented by the following formula (1), and the alkali-soluble polymer has a softening point of 150.degree. C. or more and an average molecular weight of 3000 to 8000. When used as photoresist, the composition can form a fine resist pattern. ##STR1## where R.sub.1 and R.sub.2 are either the same or different, each of which represents at least one selected from the group consisting of hydrogen, halogen atom, cyano group, nitro group, silyl group, and monovalent organic group; X represents >C.dbd.O or --SO.sub.2 --; Y represents a divalent organic group; R.sub.1 and R.sub.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: July 26, 1994
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naoko Kihara, Fumihiko Yuasa, Tohru Ushirogouchi, Tsukasa Tada, Osamu Sasaki, Takuya Naito, Satoshi Saito
  • Patent number: 5332650
    Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5 which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: July 26, 1994
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5328797
    Abstract: The present invention relates to a process for producing a negative-working photosensitive lithographic printing form, in which a negative-working photosensitive mixture which is dissolved in a solvent mixture and which contains a negative-working photosensitive compound and a polymeric binder which is insoluble in water but soluble in aqueous alkaline solution is applied to a base and the layer obtained is subsequently dried, which process comprises using a mixture of more than 2% by weight of at least one monoether of diethylene glycol with one or more organic solvent(s) having a boiling point below 200.degree. C. as the solvent mixture.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: July 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rudolf Neubauer, Roman Keiper, Siegfried Nuernberger, Sabine Pilger
  • Patent number: 5320928
    Abstract: A photosensitive composition comprising a sensitizing amount of light-sensitive diazonium compound and a polyurethane resin binder in an amount sufficient to improve physical property of the composition, wherein said polyurethane resin has at least one group selected from a phosphonic acid group, a phosphoric acid group and ester groups thereof in an amount sufficient to improve adhesion to a support. The photosensitive composition of the present invention provides an excellent adhesion to a support, an excellent developability with an aqueous alkali developer, and a high printing durability.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: June 14, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 5316892
    Abstract: A negative-working lithographic printing plate having a radiation-sensitive layer comprising a diazo resin, an acid-substituted ternary acetal polymer and an unsaturated polyester is developed with an aqueous developing composition comprising an organic solvent, an anionic surface active agent, sodium oxalate, sodium nitrate or an alkali metal tetraborate an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid and sufficient alkaline buffering system to provide an alkaline pH. The method effectively avoids problems of blinding and background sensitivity which are of critical concern in the printing art.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: May 31, 1994
    Assignee: Eastman Kodak Company
    Inventors: John E. Walls, Gary R. Miller, Raymond W. Ryan, Jr.
  • Patent number: 5310618
    Abstract: A light-sensitive composition comprising either an alkali-soluble resin or radical-polymerizable, unsaturated compound, and a diazonium compound represented by general formula (I) or (II):(S).sub.1 --(L.sup.1).sub.m --(D).sub.n (I)--(L.sup.2 (S)).sub.o --(L.sup.3 (D)).sub.P -- (II)wherein D is a diazonium salt group, S is a light absorbing group, L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and D, provided that S and D are not conjugated by L.sup.1, L.sup.2 and L.sup.3 ; l, m, n, o and p are integers.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: May 10, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kouichi Kawamura
  • Patent number: 5308735
    Abstract: Disclosed is a photosensitive diazo resin for lithographic printing represented by the formula: ##STR1## wherein X.sup.- is a counter anion, Y is a divalent bonding group selected from the group consisting of --NH--, --S-- and --O--, R.sub.1, R.sub.2 and R.sub.3 are groups which are independently selected from the group consisting of hydrogen, an alkyl group and an alkoxy group, R.sub.4 and R.sub.5 are groups which are independently selected from the group consisting of hydrogen, an alkyl group and a phenyl group, 1 and m are integers which satisfy the relation:1+m=2 to 100, 1/m=30 to 99/1 to 70and A is a quaternary ammonium salt-containing group represented by the formula: ##STR2## (wherein B is a straight or branched divalent C.sub.1-10 alkyl group which bonds to an aromatic ring by a group selected from the group consisting of --CH.sub.2 --, --CO--, --O--, --S-- and --N--, and R.sub.6, R.sub.7 and R.sub.8 are groups which are independently selected from the group consisting of hydrogen and a C.sub.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: May 3, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Edward Lam, Osamu Nanba
  • Patent number: 5302487
    Abstract: The invention describes a solvent mixture for photohardenable compositions, which includes(a) a first component having(i) a first constituent of(aa) a polar solvent of the formula R-OH, wherein R is a H or alkyl, or(aa') a monoalkylether or an alkylether ester of a glycol and constituent of(ii) a second an organic solvent having a boiling point in the range of from about 60.degree. to 160.degree. C. and comprising an aliphatic ketone, an alkanoic acid alkylester, a hydroxyalkanoic acid alkylester or a cyclic ether,in quantitative proportions selected to form a homogeneous mixture, andb) from about 0.1 to 8% by weight, relative to the total solvent mixture, of another solvent, the boiling point of which is higher than each individual boiling point of the constituents of the first component (a). The solvent mixture is used to obtain coating solutions layers which have a higher photosensitivity than corresponding layers prepared without the addition of component (b).
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: April 12, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Reinhold Arneth, Eberhard Hehl, Werner Frass, Guenter Jung
  • Patent number: 5300397
    Abstract: A light-sensitive composition comprising a diazonium compound and a polymer binder wherein the polymer binder comprises structural units represented by the following formula (I); ##STR1## wherein X represents a single bond, an ester bond or an amide bond; and Y represents a polymer group comprising structural units represented by the following formula (II); ##STR2## where Z represents ##STR3## R.sup.1 and R.sup.3 represent hydrogen atom or methyl group; R.sup.2 and R represent a single bond or a divalent bridging group; and R.sup.5 and R.sup.6 represent hydrogen atom or optionally substituted hydrocarbon group having 1 to 15 carbon atoms; and R.sup.7 represents an optionally substituted hydrocarbon group having 1 to 15 carbon atoms. The present light-sensitive composition exhibits extremely enhanced sensitivity and hence gives sufficient image formation with a short light exposure time.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: April 5, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Keitaro Aoshima
  • Patent number: 5279917
    Abstract: A light-sensitive composition comprises a light-sensitive compound, an alkali soluble resin and a fluorine-containing surfactant. The surfactant is a copolymer of a (poyoxyalkylene)acrylate or (polyoxyalkylene)methacrylate with an acrylate or methacrylate having a fluorine-containing aliphatic group. The copolymer has a weight average molecular weight of 1000 to 6000 and contains the acrylate or methacrylate in an amount of 10 to 25% by weight. The fluorine-containing aliphatic group has 6 to 20 carbon atoms and 30% or more by weight of fluorine atoms.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: January 18, 1994
    Assignee: Konica Corporation
    Inventors: Yutaka Adachi, Hideyuki Nakai, Takeshi Tanaka
  • Patent number: 5278022
    Abstract: A polymeric compound is derived from a polyhydric material and has pendant sulphonate groups of the general formula ##STR1## where X is an aliphatic, aromatic, carbocylic or heterocyclic group; Y is hydrogen, halogen or an alkyl, aryl, alkoxy, aryloxy or aralkyl group, CO.sub. --Z.sup.+, CO.sub.2 R or SO.sub.3 -Z.sup.+ ; Z.sup.+ is a cationic counter ion and R is hydrogen, alkyl, alkylene, aryl or aralkyl group.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: January 11, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John R. Wade, Robert A. W. Johnstone
  • Patent number: 5278030
    Abstract: A developer liquid for image-wise exposed radiation sensitive compositions comprises ethyl hexyl sulphate, a surfactant, and alkaline material such that the pH is al least 12 and preferably at least 13.5. The developer liquid may additionally include a water soluble carboxylic acid salt such as sodium octanoate and the sodium salt of ethylene diamine tetra acetic acid. Such developer liquids can be formulated for use with both positive-working and negative-working compositions.
    Type: Grant
    Filed: November 6, 1990
    Date of Patent: January 11, 1994
    Assignee: Du Pont-Howson Limited
    Inventors: Michael Ingham, Paul A. Styan
  • Patent number: 5275907
    Abstract: Photosensitive compositions, useful in lithographic printing plates which can be developed with aqueous developing solutions, comprise a diazo resin, an acid-substituted ternary acetal polymer, and a copolyester of an unsaturated dicarboxylic acid and an oxyalkylene ether of an alkylidene diphenol. The acid-substituted ternary acetal polymers are comprised of recurring units which include three six-membered cyclic acetal groups, one of which is unsubstituted or substituted with an alkyl or hydroxyalkyl group, another of which is substituted with an aromatic or heterocyclic moiety, and a third of which is substituted with an acid group, an acid-substituted alkyl group or an acid-substituted aryl group.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: January 4, 1994
    Assignee: Eastman Kodak Company
    Inventor: John E. Walls
  • Patent number: 5272035
    Abstract: A light-sensitive composition comprising (a) a diazonium compound, (b) a polyurethane resin having a substituent group with an acidic hydrogen atom, and (c) a compound of the following general formula: ##STR1## wherein X is a single bond, --O--, --CH.sub.2 --, or --CH.sub.2 O--; Y is an alkyl group, a hydroxy group, an alkoxy group, a nitro group or a halogen atom; n is an interger of from 0 to 5; R is a hydrogen atom, an alkyl group, a phenyl group or a substituted phenyl group; and wherein, when n.gtoreq.2, Y may be the same or different.Also disclosed is a photosensitive lithographic printing plate having a support and a light-sensitive layer deposited thereon. The light-sensitive layer comprises the above novel light-sensitive composition.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: December 21, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiyuki Sekiya
  • Patent number: 5264318
    Abstract: A positive type photosensitive composition developable with water or warm water alone of water-soluble photocrosslinking agent, water-soluble resin and synthetic resin emulsion and further a coloring agent, if necessary.
    Type: Grant
    Filed: January 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Norio Yabe, Kuniaki Monden, Hisashi Mino
  • Patent number: 5262270
    Abstract: Photosensitive compositions, useful in lithographic printing plates which can be developed with aqueous developing solutions, comprise a diazo resin and a binary acetal polymer which functions as a polymeric binder. The binary acetal polymers are comprised of recurring units which include two six-membered cyclic acetal groups, one of which is unsubstituted or substituted with an alkyl or hydroxyalkyl group and the other of which is substituted with an aromatic or heterocyclic moiety.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: November 16, 1993
    Assignee: Eastman Kodak Company
    Inventor: John E. Walls
  • Patent number: 5260161
    Abstract: Disclosed is a photosensitive composition comprising a diazo resin and a polymeric compound containing a structural unit represented by the following formula (I) in the molecule: ##STR1## wherein J represents a divalent linking group and n is 0 or 1. Disclosed is also a photosensitive lithographic printing using the photosensitive composition.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: November 9, 1993
    Assignees: Konica Corporation, Mitsubishi Kasei Corporation
    Inventors: Toshiyuki Matsumura, Shinichi Matsubara, Masafumi Uehara, Shinichi Bunya, Eriko Katahashi
  • Patent number: 5254429
    Abstract: The present invention provides photopolymerizable coating compositions comprising (a) a photosensitive compound selected from the group consisting of photoinitiators and negative-working photosensitive substances which are present in an amount effective to render the compositions sensitive to radiant energy, and (b) an ethylenically unsaturated, urethane-containing, self-crosslinkable grafted cellulose ester polymer; imaging elements for use in offset printing processes prepared therefrom; and processes employing said imaging elements.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: October 19, 1993
    Assignee: Anocoil
    Inventors: Robert F. Gracia, Shek C. Hong, William J. Ryan
  • Patent number: 5254431
    Abstract: A radiation sensitive material suitable for the production of radiation sensitive plates for lithographic printing plate manufacture comprises a polymer having appendent azide-substituted aromatic ester groups and sulphonyl urethane groups. The radiation sensitive compound is produced by a process in which some hydroxyl and/or epoxide groups of a polymer are reacted with an azide substituted carboxylic acid or ester forming derivative thereof, and some hydroxyl groups are reacted with a sulphonyl isocyanate.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: October 19, 1993
    Assignee: Vickers plc
    Inventors: Terence Etherington, Victor Kolodziejczyk
  • Patent number: 5250393
    Abstract: A method for preparinq a lithographic printing plate comprising the steps of imagewise exposing, to light, a negative-working presensitized plate for use in making a lithographic printing plate which comprises a substrate provided thereon with a light-sensitive layer comprising an aromatic diazonium compound having at least one member selected from the group consisting of carboxyl groups, phenolic hydroxyl groups, sulfonic acid residues, sulfinic acid residues and phosphorus atom-containing oxyacid residues and developing the imagewise exposed presensitized plate with a developer which comprises an aqueous solution of an alkali metal or ammonium silicate having a ratio: [SiO.sub.2 ]/[M], wherein [SiO.sub.2 ] and [M] represent the molar concentrations of SiO.sub.2 and the alkali metal or ammonia in the developer respectively, ranging from 0.15 to 0.75 and an SiO.sub.2 content ranging from 1.0 to 4.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: October 5, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanori Imai, deceased, Keiji Akiyama, Tadao Toyama, Akinobu Koike
  • Patent number: 5242779
    Abstract: A photosensitive mixture is disclosed that contains a photocurable compound, for example, a diazonium salt polycondensation product, or a photocurable combination of compounds, for example, a photopolymerizable mixture, and a polymeric binder, which binder is a graft copolymer with a polyurethane graft backbone onto which chains containing vinyl alcohol units and vinyl acetal units derived from hydroxyaldehydes are grafted. The mixture is suitable for use in the production of printing plates and photoresists, can be developed with purely aqueous solutions, and gives printing plates distinguished by high resistance to mechanical and chemical attacks.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: September 7, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Waltraud Mueller-Hess, Dieter Mohr, Matthias Kroggel
  • Patent number: 5240807
    Abstract: A water soluble built-on mask layer is provided on a photoresist composition disposed on a substrate. The photoresist comprises an o-quinone diazide and a novolak or paravinyl phenol resin. The built-on mask layer comprises a water soluble, photobleachable diazonium salt, a coupler for the diazonium salt and an acidic, polymeric, film forming resin such as polystyrene sulfonic acid.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: August 31, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Sangya Jain, Salvatore Emmi, Thomas S. Phillips
  • Patent number: 5240808
    Abstract: A light-sensitive composition which comprises at least one polymeric compound having both photocross-linkable groups and functional groups carrying P--OH bonds. The light-sensitive composition can effectively be employed for making lithographic printing plates, IC circuits and photomasks. The light-sensitive composition shows excellent practically acceptable developability with either of an aqueous alkali developer and an aqueous alkaline solution containing or free of organic substances such as organic solvents and/or surfacants. Moreover, when it is used to form PS plates, the resulting lithographic printing plates never cause background contamination and can provide a large number of good printed matters. The composition makes it possible to develop negative working PS plates with developers for positive working PS plates. Therefore, when both positive and negative working PS plates are processed, the use of the composition can save various troubles.
    Type: Grant
    Filed: January 8, 1992
    Date of Patent: August 31, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keitaro Aoshima, Masanori Imai
  • Patent number: 5238772
    Abstract: A photopolymerizable mixture is disclosed which contains:a) a graft copolymer having a polyurethane as the graft backbone, onto chains containing vinyl alcohol units and vinyl acetal units are grafted,b) a free-radically polymerizable compound possessing at least one terminal ethylenically unsaturated group and having a boiling point of more than 100.degree. C. at normal pressure, andc) a compound or a combination of compounds which under the action of actinic light is capable of initiating the polymerization of compound b).The mixture is suitable for use in the production of printing plates and photoresists. It is distinguished by high photospeed and can be developed with aqueous solutions. It yields printing plates producing large print runs.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: August 24, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Waltraud Mueller-Hess, Dieter Mohr, Karl-Josef Rauterkus, Matthias Kroggel
  • Patent number: 5229244
    Abstract: The present invention concerns a phototackifiable composition useful as a coating on a substrate consisting of an optically clear blend of two or more polymers and a photosensitive compound that forms a strong acid on exposure to actinic radiation. The invention also relates to a process for coating such a composition on a support and toning the image-wise exposed composition on the support.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: July 20, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Walter R. Hertler, Howard E. Simmons, III
  • Patent number: 5219711
    Abstract: Excellent resolution and sensitivity in the patterning of resists utilized in device and mask manufacture is obtained with a specific composition. In particular this composition involves polymers having recurring pendant acid labile .alpha.-alkoxyalkyl carboxylic acid ester and/or hydroxyaromatic ether moieties in the presence of an acid generator comprising a novel diazonium salt.
    Type: Grant
    Filed: May 18, 1992
    Date of Patent: June 15, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert G. Anderson, Walter R. Hertler, Robert C. Wheland, Yuan Yu G. Chen
  • Patent number: 5219699
    Abstract: Photosensitive compositions, useful in lithographic printing plates which can be developed with aqueous developing solutions, comprise a diazo resin and an acid-substituted ternary acetal polymer which functions as a polymeric binder. The acid-substituted ternary acetal polymers are comprised of recurring units which include three six-membered cyclic acetal groups, one of which is unsubstituted or substituted with an alkyl or hydroxyalkyl group, another of which is substituted with an aromatic or heterocyclic moiety, and a third of which is substituted with an acid group, an acid-substituted alkyl group or an acid-substituted aryl group.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: June 15, 1993
    Assignee: Eastman Kodak Company
    Inventors: John E. Walls, Larry D. LeBoeuf
  • Patent number: 5213941
    Abstract: This invention provides an improved negative-working or positive-working, single sheet color proofing method which can accurately reproduce images by using colored, photosensitive layers on substrates which are then overcoated with partially developable adhesive layers. The final construction is useful in predicting the image quality from a lithographic printing process. The partial removal of the adhesive layers cleans out any background stain which may remain from the incomplete removal of the photosensitive layer.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: May 25, 1993
    Assignee: Hoechst Celanese Corporation
    Inventor: Stephan J. W. Platzer
  • Patent number: 5212041
    Abstract: This invention relates to water developable, negative working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process. The invention provides both overlay and transfer type proofing sheets which have good fingerprint resistance.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: May 18, 1993
    Assignee: Hoechst Celanese Corporation
    Inventor: Stanley F. Wanat
  • Patent number: 5210003
    Abstract: Non-polymeric compounds which contain at least one aromatic ring system carrying one or more one or more tetrahydropyranyloxy substituents of formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl, cycloalkyl, aryl, alkoxy or aryloxy,R.sub.2 is hydrogen, alkyl, cycloalkyl or aryl,R.sub.3 is a saturated or unsaturated hydrocarbon radical,R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, alkyl, alkoxy or aryloxy, andX is a direct single bond or a methylene or ethylene bridge.These compounds are especially suitable for the preparation of photoresist compositions which can be used both for the production of positive as well as negative images. The photoresists are preferably used for deep-UV microlithography.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: May 11, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schadeli
  • 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