Polymeric Mixture Patents (Class 430/176)
  • Patent number: 5691101
    Abstract: Disclosed are a safe slurry photosensitive composition superior in image formation capabilities such as resolution and sensitivity and containing no harmful compound, and a safe water-soluble photosensitive composition capable of being dissolved in water without using any organic solvent while maintaining a sufficient sensitivity as a resist and containing no harmful substance. The slurry photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, at least one type of a resin with acid-crosslinkability or acid-decomposability, and a powder. Various devices can be manufactured by forming a layer of this photosensitive composition on a substrate, exposing the layer to light in accordance with a desired pattern, and heating the layer. The water-soluble photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, and an acetal resin.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: November 25, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Naomi Shida, Takuya Naito, Koji Asakawa, Akinori Hongu, Makoto Nakase, Hirokazu Niki
  • Patent number: 5688627
    Abstract: A water soluble diazonium salt composition made by the condensation of diazoaryl amines and aldehydes and precipitated to form a polymeric anionic species having both ZnCl.sub.4.sup.= and HSO.sub.4.sup.- moieties. These composition are blended with suitable binders, colorants and other optional components to produce light sensitive coating compositions. When applied to aluminum substrates, these light sensitive coating compositions form lithographic printing plates that are especially stable under high humidity conditions. Such plates may be developed by either water alone or by water which contains surfactants and/or a small amount of an organic solvent.
    Type: Grant
    Filed: July 2, 1996
    Date of Patent: November 18, 1997
    Assignee: Precision Lithograining Corp.
    Inventor: Albert S. Deutsch
  • Patent number: 5688628
    Abstract: A resist composition comprising in admixture (A) a compound which forms an acid upon exposure to active rays, (B) a polymer which has at least one structural unit with a group unstable to an acid and cleaves at this group in the presence of the acid derived from the compound (A) to turn alkali-soluble, and (C) a phenolic compound, and a process for forming a resist pattern using this resist composition are provided.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: November 18, 1997
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Nobunori Abe, Hideyuki Tanaka, Akira Oikawa, Shuichi Miyata
  • Patent number: 5672463
    Abstract: A polyfunctional vinyl ether compound represented by formula (I): ##STR1## wherein n, which is an average repeating number, represents a number of from 0 to 20; R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, or a cycloalkyl group; Q each independently represents --OH or a group represented by the formula --OROCH.dbd.CH.sub.2, wherein R represents an alkylene group having from 1 to 12 carbon atoms, the molar ratio of (--OH)/(--OROCH.dbd.CH.sub.2) being from 10/90 to 90/10; and A each independently represents a divalent hydrocarbon group having from 1 to 30 carbon atoms.
    Type: Grant
    Filed: October 20, 1995
    Date of Patent: September 30, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeo Hozumi, Shinichiro Kitayama, Hiroya Nakagawa
  • Patent number: 5667930
    Abstract: A photopolymerization photoresist composition having a binder resin, a multifunctional compound, a photopolymerization initiator, a sensitizer and other additives. The photopolymerization initiator has one or more 4,6-bis(chloromethyl)-s-triazine compound containing a diazophenyl group. The initiator acts as a chromophore and is represented by the following general formula I: ##STR1## wherein the position at which the diazo group bonds to phenyl group may be changed. R is an aliphatic radical or an unsubstituted- or substituted aromatic radical and n is an integer of 0 to 2.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: September 16, 1997
    Assignee: Cheil Synthetics Incorporation
    Inventors: Bo Sung Kim, Soon Sik Kim, Dae Woo Ihm
  • Patent number: 5663031
    Abstract: The present invention provides an imaging element comprising on a support in the order given a coated composition of at least two hydrophilic layers being in water permeable contact with each other and each containing a hydrophilic (co)polymer or (co)polymer mixture and having been hardened with a hydrolyzed tetraalkyl orthosilicate and a light sensitive layer containing a diazo resin or a diazonium salt characterized in that the ratio by weight in the top layer of said package of said hydrophilic (co)polymer or (co)polymer mixture versus said hydrolyzed tetraalkyl orthosilicate (expressed as silicon dioxide) is at least 1.1 and the ratio by weight in an underlying layer of said package of said hydrophilic (co)polymer or (co)polymer mixture versus said hydrolyzed tetraalkyl orthosilicate (expressed as silicon dioxide) is not higher than 0.9.
    Type: Grant
    Filed: January 29, 1996
    Date of Patent: September 2, 1997
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Guido Hauquier, Joan Vermeersch, Eric Verschueren, Dirk Kokkelenberg, Willem Cortens
  • Patent number: 5658706
    Abstract: A resist composition for forming a pattern, which comprises (a) a compound represented by the following formula (1) and satisfying the following inequalities, ##STR1## wherein R.sup.1 is hydrogen atom or methyl group, R.sup.2 is a monovalent organic group, m is 0 or a positive integer, n is a positive integer, and m and n satisfying a condition of 0.03.ltoreq.n/(m+n).ltoreq.1, (b) a compound capable of generating an acid when irradiated with light, and (c) a nitrogen-containing compound, wherein a weight-average molecular weight, Mw and a number-average molecular weight, Mn satisfy the following inequality, 4,000.ltoreq.Mw.ltoreq.50,000, 1.10.ltoreq.Mw/Mn.ltoreq.2.50 (Mw and Mn respectively represent value converted in styrene).
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: August 19, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Hirokazu Niki, Hiromitsu Wakabayashi, Rumiko Hayase, Naohiko Oyasato, Yasunobu Onishi, Kazuo Sato, Kenji Chiba, Takao Hayashi
  • Patent number: 5654121
    Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I) ,R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: August 5, 1997
    Assignee: Agfa-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5650261
    Abstract: A positive-acting photoresist composition which produces crosslinked images and processes for using the photoresist composition are disclosed. The photoresist composition is prepared from a mixture containing a film forming, polymer-containing, acid hardening resin system, an acid or acid generating material (preferably in the form of a thermal acid generator) for crosslinking the acid hardening resin system, and a photobase generating compound. The photoresist composition is applied as a film onto a substrate surface and selectively imagewise exposed through a photomask to actinic radiation. The actinic radiation causes the photobase generator to produce a base in the imagewise exposed portions of the photoresist film. The photochemically generated base neutralizes the acid in the imagewise exposed areas of the photoresist film.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: July 22, 1997
    Assignee: Rohm and Haas Company
    Inventor: Mark Robert Winkle
  • Patent number: 5645975
    Abstract: The invention resides in a photosensitive composition for screen printing. Preferably, the composition of the invention comprises a polymer comprising a vinylpyridine monomer or polymer having a pyridinium salt character and a photoreactable constituent. The resulting stencil, once dried, exposed, cured, and subjected to alkaline treatment obtains enhanced solvent/water resistance but can be reclaimed using an acidic wash. In use, the stencil provides a screen/stencil assembly or blockout utility of high structural integrity through repeated use and screen printing images of high resolution and quality.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 8, 1997
    Assignee: The Chromaline Corporation
    Inventors: Alexander S. Gybin, Kyle K. Johnson, Toshifumi Komatsu, Lawrence C. Vaniseghem
  • Patent number: 5639586
    Abstract: The present invention provides a lithographic base comprising on a hydrophobic support a packet of subbing layers contiguous to a hydrophilic layer containing a hydrophilic (co)polymer or (co)polymer mixture and being hardened with a hydrolysed tetraalkyl orthosilicate crosslinking agent characterized in that said packet of subbing layers contains as undermost layer a layer comprising, a polymer latex having hydrophilic functionality and as uppermost layer a layer comprising a hydrophilic binder and silica in a weight ratio of the hydrophilic binder to silica of less than 1.
    Type: Grant
    Filed: August 14, 1995
    Date of Patent: June 17, 1997
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Guido Hauquier, Willem Cortens, Paul Coppens, Joan Vermeersch, Erik Mostaert, Eric Verschueren
  • Patent number: 5637435
    Abstract: A negative-type photosensitive lithographic printing plate having a photosensitive layer comprising upper and lower layers, each layer containing a photosensitive diazo resin, on a support having a hydrophilic surface. The concentration of the diazo resin in the upper layer is not more than 1/3 of the concentration of the diazo resin in the lower layer, the thickness of the upper layer is not less than three times the thickness of the lower layer, and the upper layer contains an oleophilic non-photosensitive resin with a weight average molecular weight ranging from 10,000 to 150,000. The lithographic printing plate has a very short exposure time, may be used with projection exposure systems and allows for the use of known developers and automated developer systems.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: June 10, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventor: Shigeki Shimizu
  • Patent number: 5635284
    Abstract: Monochrome and polychrome color proofs, for the graphic arts industry, having an image carrier containing two layers A and B to control optical dot growth are described. Layer A contains at least one polyolefin and, in a preferred embodiment, a light-reflecting white pigment. Layer B contains at least one binder, at least one light-reflecting white pigment at between 50% and 90% by weight relative to Layer B, and at least one light-absorbing pigment. A process and a means for preparing such monochrome and polychrome color proofs are described.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: June 3, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Bernhard Metzger, Ursula A. Kraska, Mario Grossa
  • Patent number: 5633112
    Abstract: A photosensitive resin composition comprising (a) a polymer having carboxyl groups (b) a photoacid generator which generates an acid when irradiated with light, and (c) an aliphatic amine is capable of development with ease by use of a wide variety of aqueous solvents.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: May 27, 1997
    Assignees: Hitachi, Ltd., Hitachi Chemical Company, Ltd.
    Inventors: Takao Miwa, Yoshiaki Okabe, Mina Ishida, Akio Takahashi, Shunichi Numata
  • Patent number: 5629135
    Abstract: Positive-tone and negative-tone chemically amplified resist compositions comprising: (a-1) a blocked resin, (a-2) a combination of an alkali-soluble resin and a dissolution controlling agents, or (a-3) a combination of an alkali-soluble resin and a crosslinking agent, (b) a photoacid generator, and (c) specific kinds of solvents. The both positive-tone and negative-tone resist compositions exhibits superior sensitivity, high resolution capability, and excellent storage stability, and can be excellently applied especially to large sized substrates by spincoating for producing excellently shaped patterns by irradiation. The compositions can be used with advantage as a chemically amplified resist for the manufacture of semiconductor devices or integrated circuits (ICs).
    Type: Grant
    Filed: January 29, 1996
    Date of Patent: May 13, 1997
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Eiichi Kobayashi, Makoto Murata, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5618868
    Abstract: The present invention is concerned with a novel azo compound represented by formula (1), (2) or (3), a water-soluble dye comprising this azo compound, and a polarizing film containing this azo compound. The obtained polarizing film has high hydrothermoresistance and a high polarization degree and is excellent in optical characteristics: ##STR1## wherein each of R.sub.1, R.sub.3 and R.sub.12 is independently a hydrogen atom, halogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.2, R.sub.4, R.sub.8 and R.sub.9 is independently a hydrogen atom, hydroxyl group, alkyl group having 1 or 2 carbon atoms, alkoxy group having 1 or 2 carbon atoms, or acetylamino group; R.sub.5 is a hydroxyl group or amino group at the o-position or p-position to the azo group; each of R.sub.6 and R.sub.10 is a hydrogen atom, carboxyl group, or alkoxy group having 1 or 2 carbon atoms; each of R.sub.7 and R.sub.
    Type: Grant
    Filed: April 6, 1994
    Date of Patent: April 8, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsutami Misawa, Akira Ogiso, Rihoko Imai, Hisato Itoh
  • Patent number: 5589315
    Abstract: A photosensitive composition containing a polyfunctional aromatic diazo compound having at least two groups of Formula (uD) in the molecule, and a photosensitive composition using the same. The diazo compound can be handled under visible light free from ultraviolet, is highly photosensitive, has good shelf life, and lithographic printing plates and screen printing plates formed with the same: ##STR1## wherein G.sup.1 is a substituent derived from alcoholic hydroxyl group; R.sup.1 and R.sup.2 are hydrogen, or alkyl or alkyloxy of 1 to 8 carbon atoms;R.sup.3 is alkyl or substituted alkyl of 1 to 8 carbon atoms, aralkyl or substituted aralkyl of 7 to 14 carbon atoms, or --CH.sub.2 CHG.sup.2 --CH.sub.2 --;X.sup.- is an anion based on protonic acid from which a proton is removed.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: December 31, 1996
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Noriaki Tochizawa, Yasuo Kuniyoshi, Masaharu Watanabe, Katsuyo Tokuda, Ichiro Hozumi
  • Patent number: 5580702
    Abstract: Disclosed herein is a resist for forming patterns, which is greatly sensitive to ultraviolet rays an ionizing radiation, and which can therefore form a high-resolution resist pattern if exposed to ultra violet rays or an unionizing radiation. Hence, the resist is useful in a method of manufacturing semicon ductor devices having high integration densities. The resist comprises tert-butoxycarbonyl methoxypolyhydroxy styrene and an o-quinonediazide compound.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: December 3, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Noahiko Oyasato, Yoshihito Kobayashi, Shuzi Nayase
  • Patent number: 5576136
    Abstract: According to the present invention the storage stability of a diazo based imaging element can be improved by controlling the amount of free water in the imaging element. Thus the present invention provides an imaging element comprising on a support a hydrophilic layer containing a hydrophilic (co)polymer or (co)polymer mixture and having been hardened with a hydrolyzed tetraalkyl orthosilicate and a light sensitive layer containing a diazo resin or a diazonium salt characterized in that the total amount of free water in said imaging element satisfies the following formula (I):FW (g/m.sup.2).ltoreq.0.0043 * WS (g/m.sup.2)+0.46 (g/m.sup.2) (I)wherein FW represents the amount of free water and WS represents the weight of the support of the imaging element.
    Type: Grant
    Filed: June 29, 1994
    Date of Patent: November 19, 1996
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Joan Vermeersch, Eric Verschueren, Guido Hauquier
  • Patent number: 5567568
    Abstract: A photosensitive composition comprising (A) an ethylenically unsaturated addition-polymerizable compound, (B) an aqueous alkali-soluble or swelling polymer which is capable of forming a film, (C) a photopolymerization initiator, (D) a negative-working diazo resin, and (E) a component which is soluble in a photosensitive solution, but floats on a surface of a photosensitive layer and is capable of forming an oxygen-intercepting layer during coating and drying is described. A photosensitive lithographic printing plate comprising a support coated with the above-described photosensitive composition and a matting layer provided thereon, wherein the surface of the matting layer has a micro pattern comprising (i) a portion which is coated with a composition comprising a copolymer containing at least one monomer unit having a sulfonic acid group and (ii) a portion which is uncoated with the composition is also descried.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: October 22, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Akira Nishioka
  • Patent number: 5556733
    Abstract: A thermal development diazo copying material is composed of a support, a diazo layer which contains a diazo compound, and a coupler layer which contains a coupling component, an alkali-soluble resin and a thermofusible material, which are overlaid on the support.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: September 17, 1996
    Assignee: Ricoh Company, Ltd.
    Inventors: Shigeru Kusakata, Masanori Rimoto
  • Patent number: 5554465
    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: May 23, 1995
    Date of Patent: September 10, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5552260
    Abstract: Acid-sensitive polymers and imageable articles employing them are disclosed. In particular, photosensitive compositions are disclosed comprising: (a) a photoinitiator which generates an acid upon exposure to radiation; and (b) a polymer having acid labile groups pendant from the polymer backbone, said acid labile pendant groups comprising at least one each of A and B wherein A has the formula --T-(C.dbd.O)OCR.sup.1 R.sup.2 OR.sup.3, and B has the formula --T-(C.dbd.O)OR.sup.4 Si(R.sup.5).sub.3, wherein R.sup.1 and R.sup.2 each represent H or an alkyl group with the proviso that at least one of R.sup.1 and R.sup.2 must be hydrogen; R.sup.3 represents an alkyl group; or any two of R.sup.1, R.sup.2, and R.sup.3 may together form a ring group having from 3 to 36 carbon atoms; R.sup.5 represents an alkyl group, aryl group, an alkoxy group, an aryloxy group, an acyloxy group, or a trialkylsiloxy group; and R.sup.4 and T represents a divalent linking group wherein T is bonded to the polymer backbone and R.sup.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: September 3, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dennis E. Vogel, Leonard J. Stulc
  • Patent number: 5547808
    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: September 9, 1994
    Date of Patent: August 20, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5543260
    Abstract: A diazo heat-sensitive recording material containing a support having provided thereon a recording layer containing a diazo compound, a coupler, and an organic base, wherein the diazo compound is a compound represented by formula (I): ##STR1## wherein R.sub.1 represents --C(Z.sub.1)(Z.sub.2)--CH.sub.2 --A, --CH.sub.2 --C(Z.sub.1)(Z.sub.2)--A or --{C(Z.sub.1)(Z.sub.2)}.sub.m --A,wherein Z.sub.1 represents an alkyl group, an aralkyl group or an aryl group; Z.sub.2 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group; A represents a halogen atom, an acyl group, a cyano group, or a group containing at least one oxygen, nitrogen, phosphorus or sulfur atom through which A is bonded to --CH.sub.2 -- or Z.sub.2 ; and m represents an integer of 1 to 5;R.sub.2 and R.sub.3, which may be the same or different, each represent an alkyl group, an aralkyl group or an aryl group; R.sub.1 and R.sub.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: August 6, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiichi Tateishi, Sadao Ishige, Hiroshi Kamikawa
  • Patent number: 5536616
    Abstract: A photoresist is provided. The photoresist comprises a polymer, a photoactive agent, and a crosslinking agent. The crosslinking agent comprises a water soluble sugar. The present invention also provides a method of making microelectronic structures.
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: July 16, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Sze-Ming Lee
  • Patent number: 5534381
    Abstract: This invention is an acetal polymer having the following repeating units: ##STR1## where R is an alkyl group of 1 to 10 carbon atoms;Ar.sub.1 is an aromatic group substituted with an aliphatic group containing 3 to 20 carbon atoms or an alkoxy group having 3 to 20 carbon atoms;Ar.sub.2 is a non-substituted aromatic group;A.sub.1 is an acid group;n.sub.1, n.sub.2, n.sub.3, n.sub.4, n.sub.5 represent the molar percents of the respective repeating units and n.sub.1 is 0-20 mole %, preferably 2-10 mole %; n.sub.2 is 2-20 mole %, preferably 5 to 15 mole %; n.sub.3 is 15-85 mole %, preferably 20 to 65 mole %; n.sub.4 is 0 to 40 mole %, preferably 0 to 20 mole %; and n.sub.5 is 5-40 mole %, preferably 20 to 35 mole %. These polymers may be used in photosensitive compositions and lithographic printing plates.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: July 9, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: M. Zaki Ali, Mahfuza B. Ali
  • Patent number: 5529886
    Abstract: The invention relates to monomers of the formulae R.sup.1 -SO.sub.2 -N(CO-OR.sup.2)-R3-O-CO-CR.sup.4 =CH.sub.2 and R.sup.1 -N(CO-OR.sup.2) -SO.sub.2 -R.sup.3 -O-CO-CR.sup.4 =CH.sub.2, in which R.sup.1 is a (C.sub.1 -C.sub.20)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical, individual methylene groups in the radicals containing alkyl being optionally replaced by heteroatoms, R.sup.2 is a (C.sub.3 -C.sub.11)alkyl, C.sub.3 -C.sub.11) alkenyl or (C.sub.7 -C.sub.11)aralkyl radical, R.sup.3 is an unsubstituted or substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical and R.sup.4 is a hydrogen atom or a methyl group. It further relates to polymers having at least 5 mol % of units with pendent groups of the formula(e) -R.sup.3 -N(CO-OR.sup.2)-SO.sub.2 -R.sup.1 (I) and/or -R.sup.3 -SO.sub.2 -N(CO-OR.sup.2)-R.sup.
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: June 25, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5527655
    Abstract: Radiation-sensitive polymeric adducts of (1) a sulfonated polyester resin having a plurality of sulfonate groups, (2) a diazonium resin having a plurality of diazonium groups, and (3) a salt of quaternary ammonium or quaternary phosphonium. This invention also provides a radiation-sensitive article comprising a substrate bearing a coating containing a radiation-sensitive adduct.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: June 18, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: James A. Bonham, Leonard J. Stulc, Richard J. Kuo, Kimberly R. Kukla
  • Patent number: 5527659
    Abstract: There is described a chemical amplification resist composition which comprises squarylium compounds represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent substituted or unsubstituted aminophenyl, 9-julodidyl, Y.dbd.CH-- (wherein Y represents substituted or unsubstituted heterocyclic group containing nitrogen, or a group: ##STR2## (wherein Z.sup.1 and Z.sup.2 are the same or different and represent substituted or unsubstituted phenyl), photochemical acid generator and binders.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: June 18, 1996
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tsuguo Yamaoka, Kenichi Koseki, Mitsuharu Obara, Ikuo Shimizu, Yukiyoshi Ito
  • Patent number: 5506089
    Abstract: A universal method to make photosensitive polymers from poly(vinyl alcohol) and poly(vinyl pyridine) is disclosed which generally does not require final purification and can produce photosensitive polymers which are of similar photosensity whether prepared with a poly(vinyl alcohol) or poly(vinyl pyridine) backbone. These polymers comprise a heterocyclic, light-sensitive pendant group including a moiety having the formula: ##STR1## wherein Z.sup.1 denotes the atoms necessary to form a substituted or unsubstituted aromatic heterocyclic ring; Z.sup.2 denotes the atoms necessary to form a substituted or unsubstituted aromatic or aromatic heterocyclic ring; R is hydrogen or a substituted or unsubstituted alkyl group; M is a divalent organic moiety; Y is a residue from a grafting group that is capable of grafting the pendant group onto a polymeric backbone.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: April 9, 1996
    Assignee: The Chromaline Corporation
    Inventors: Alexander S. Gybin, Lawrence C. Van Iseghem
  • Patent number: 5496678
    Abstract: A photosensitive composition which comprises, as essential components:(A) a polymer having carboxyl group(s) and hydroxyphenyl group(s), or (A') a polymer having carboxyl group(s) and (A") a polymer having hydroxyphenyl group(s),(B) a compound having at least two vinyl ether groups in the molecule, and(C) a compound which generates an acid when irradiated with an actinic ray, and which is useful as a positive type photoresist having high resolution and excellent formability of fine image pattern, a material for printing, etc.; and a process for pattern formation using said composition.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: March 5, 1996
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Genji Imai, Naozumi Iwasawa, Tsuguo Yamaoka
  • Patent number: 5482816
    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: June 21, 1994
    Date of Patent: January 9, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5478690
    Abstract: Disclosed is an alkali developable photosensitive resin composition useful for an offset printing plate, which has excellent developability and provides long life of a developer. The photosensitive resin composition comprising:(a) an alkali-soluble type binder resin,(b) a photosensitive substance, and(c) a dye;said binder resin (a) having an ampho-ionic group represented by the formula: ##STR1## [wherein R.sup.1 is H or a C.sub.1-10 alkyl group which optionally has a substituent or a functional group in a chain, R is a substituted or non-substituted C.sub.1-20 alkylene or phenylene group, and A is --COO or --SO.sub.3 ]and/or an ampho-ionic group represented by the formula: ##STR2## [wherein each R.sup.2 is the same or different and respectively indicates a C.sub.1-10 alkyl group which optionally has a substituent or a functional group in a chain, and R and A are as defined above] in a molecule and containing a resin having total acid value of 5 to 150.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: December 26, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Yoshifumi Ichinose, Seiji Arimatsu
  • Patent number: 5476751
    Abstract: The invention relates to compounds of formula I ##STR1## wherein A is a radical of formula ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 --C.sub.4 alkyl, C.sub.1 C.sub.4 alkoxy, halogen or a radical of formula ##STR3## wherein X is --O--, --CH.sub.2 --, --C(CH.sub.3).sub.2 -- or --SO.sub.2 --, and R.sub.3 and R.sub.4 are each independently of the other hydrogen, C.sub.1 --C.sub.4 alkyl or phenyl, as well as compositions comprising these compounds.The compositions are particularly suitable for making integrated circuits.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: December 19, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Alfred Steinmann
  • Patent number: 5464686
    Abstract: A PS plate requiring no dampening water comprises a substrate provided thereon with, in order, a light-sensitive resin layer and a silicone rubber layer, wherein the light-sensitive resin layer is formed from a light-sensitive composition which comprises the following components:(i) at least one monomer represented by the following general formula (I): ##STR1## (wherein R.sup.1 represents, for instance, H or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a to f each independently represents an integer; R.sup.2 and R.sup.3 each independently represents H or a methyl group); (ii) a photopolymerization initiator; and (iii) a polymeric compound having film-forming ability. The hardening properties of the silicone rubber layer is greatly improved and thus there can be obtained a PS plate exhibiting high sensitivity and hence lithographic printing plates having good printing durability.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: November 7, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tatsuji Higashi, Noboru Yasuda
  • Patent number: 5462833
    Abstract: The present invention provides a lithographic base comprising on a hydrophobic support a subbing layer and a hydrophilic layer containing a hydrophilic (co)polymer or (co)polymer mixture and being hardened with a hydrolyzed tetraalkyl orthosilicate crosslinking agent characterized in that said subbing layer contains a hydrophilic binder and silica, the surface area of the silica being at least 300 m.sup.2 per gram.
    Type: Grant
    Filed: March 9, 1994
    Date of Patent: October 31, 1995
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Guido Hauquier, Willem Cortens, Paul Coppens, Joan Vermeersch, Erik Mostaert, Eric Verschueren
  • Patent number: 5462834
    Abstract: Photographic images may be produced on a backing such as paper and polyester sheets, from photographic negatives which encompass line rendering, design comps, copy, complex color separation or the like with water-based varnishes and pigments, the resulting images closely resembling, if not exactly, the same image in its commercially printed form. Thus all aspects of color proofs produced by this invention provide greatly improved predictability as to the appearance of the final printed job, with a further improvement of cost savings over conventional techniques of preparing color proofs. Also, said proofing method can be used to provide a "transfer" so that one may transfer the colored image or images to a more suitable or required backing.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: October 31, 1995
    Inventors: Edward L. Weller, Jr., Edward J. Renkor, Edward L. Weller, III
  • Patent number: 5459011
    Abstract: A photosensitive composition including a water-soluble aromatic diazo compound having at least two diazo groups and lactic acid, hydroxyacetic acid or, a mixture thereof in an amount of at least one third by weight of the diazo compound. The photosensitive composition is in the form of a liquid or paste, is thus easy to handle, is suitable for use in the production of photosensitive printing plates, and has good storage stability.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: October 17, 1995
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Kieko Harada, Katsuyo Tokuda
  • Patent number: 5459010
    Abstract: A photosensitive composition comprising a photosensitive material and a polymer, wherein the polymer comprises from 2 to 50 mol % of hydroxyalkyl (meth)acrylate units, of which the main component is units of a hydroxyalkyl (meth)acrylate of the following formula (I): ##STR1## wherein R.sub.1 is a hydrogen atom or a methyl group, and n is an integer of from 3 to 10.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: October 17, 1995
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shigeki Shimizu, Youichiro Tsuji
  • Patent number: 5457003
    Abstract: A resist material comprises a polysiloxane obtained by hydrolysis and condensation with dehydration of one or more alkoxysilanes having an oxirane ring, or of a mixture of the alkoxysilane(s) having an oxirane ring and one or more alkoxysilanes having no oxirane ring, and an acid generator. The resist material may contain one or more of a spectral sensitizer, an organic polymer having a hydroxyl group or an epoxy compound. Resist patterns are formed by coating an organic polymer on a substrate and then the resist material on the film of the organic polymer to form a two layer resist having a bottom layer of the organic polymer and top layer of the resist material, prebaking, imagewise exposing high radiation, postbaking, and developing the resist with alkaline solutions to remove an unexposed portion of the top layer, and dry etching the bottom layer using the relic of the resist material as a mask. the temperature of the post baking is preferably lower than that of the prebaking.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: October 10, 1995
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Akinobu Tanaka, Hiroshi Ban, Jiro Nakamura, Takao Kimura, Yoshio Kawai
  • Patent number: 5445912
    Abstract: The present invention provides a lithographic base comprising on a hydrophobic support a subbing layer contiguous to a hydrophilic layer containing a hydrophilic (co)polymer or (co)polymer mixture and being hardened with a hydrolyzed tetraalkyl orthosilicate crosslinking agent characterized in that said subbing layer contains a hydrophilic binder and silica and is applied at a solids content of more than 200 mg per m.sup.2 but less than 750 mg per m.sup.2.
    Type: Grant
    Filed: March 9, 1994
    Date of Patent: August 29, 1995
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Guido Hauquier, Willem Cortens, Paul Coppens, Joan Vermeersch, Erik Mostaert, Eric Verschueren
  • Patent number: 5443937
    Abstract: A precolored, water-developable, photosensitive elements comprising:(A) a support;(B) a colorant-containing layer consisting essentially of(1) a colorant, and(2) a polyvinyl alcohol binder, said binder being about 87-100% hydrolyzed and being of sufficiently high molecular weight to be film-forming; and(C) a photosensitive layer consisting essentially of:(3) a photosensitive, water-soluble, polymeric diazo resin; and(4) a polyvinyl alcohol binder, said binder being about 87-100% hydrolyzed and being of sufficiently high molecular weight to be film-forming; and(D) an adhesive layer;wherein said colorant-containing layer (B) and said photosensitive layer (C) may be combined into a single layer colorant-containing, photosensitive coating (E) which must be in contact with the adhesive layer (D) or alternatively, said colorant-containing layer (B) and said photosensitive layer (C) may be in separate but contiguous layers provided that either layer (B) or (C) must be in contact with the adhesive layer (D), and prov
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: August 22, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Gregory A. Bodager, Robert W. Peiffer
  • Patent number: 5441837
    Abstract: An imaging member comprised of an optional supporting substrate, a photogenerator layer, and a charge transport layer, and wherein the photogenerator layer is comprised of acetoxymetal phthalocyanine pigments as essentially represented by the formula ##STR1## where R is acetyl, haloacetyl, or mixtures thereof; R' is alkyl, alkoxy, cyano, halogen, or mixtures thereof; M is a metal selected from the group consisting of aluminum, gallium, silicon, germanium and indium; x is 1 or 2; and y is 0, 1 or 2.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: August 15, 1995
    Assignee: Xerox Corporation
    Inventors: Beng S. Ong, Cheng-Kuo Hsiao
  • Patent number: 5427887
    Abstract: Disclosed is a light-sensitive composition which comprises(A) a diazo resin and(B) an alkali-soluble and swellable polymer compound, said polymer compound being a vinyl copolymer containing, as a constitutional unit, 0.1 to 10 mole % of a structure derived from an ester of acrylic acid or methacrylic acid having an alkyl group with 8 or more carbon atoms.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: June 27, 1995
    Assignees: Konica Corporation, Mitsubishi Kasei Corporation
    Inventors: Satoshi Konuma, Toshiyuki Matsumura, Akihisa Murata, Shigeo Tsuji
  • Patent number: 5424165
    Abstract: A light-sensitive composition comprises a diazo resin, a polymeric binder and a low molecular weight organic compound having at least 3 carboxyl groups and free of other functional groups containing elements other than hydrogen and carbon atoms. The composition may further comprise a compound carrying at least one phosphorus atom-containing oxoacid residue and a compound carrying at least one sulfonic acid residue. The light-sensitive composition can easily be developed with an aqueous alkaline developer, can provide a lithographic printing plate having good printing durability and has excellent storage stability. Therefore, the developability and resistance to background contamination thereof are not deteriorated even after storing under high temperature and humidity conditions over a long time period.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: June 13, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiyuki Sekiya
  • Patent number: 5424166
    Abstract: A negative-working radiation-sensitive mixture which comprisesa) a compound, which forms a strong acid on irradiation, of the general formula ##STR1## in which R.sup.1 is a radical R.sup.2 --SO.sub.2 -- or R.sup.3 --C(O)-- andR.sup.2 and R.sup.3 independently of one another are an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound containing at least two reactive groups which can be crosslinked by an acid andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions, is described.The radiation-sensitive mixture according to the invention is distinguished by a high sensitivity over a wide spectral range. It likewise exhibits a high heat stability and forms no corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: June 13, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Winfried Meier
  • Patent number: 5415971
    Abstract: A photosensitive mask laminate having a photoimageable, pressure sensitive adhesive layer and a photoimageable masking layer is disclosed. The laminate also includes a support layer, and it can include a removable carrier layer and a release layer. The laminate can be imaged by selective exposure to light or other radiation, and developing the laminate produces a mask having void and mask areas. The mask can then be used to protect selected portions of a target surface during a sandblast decorative process.
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: May 16, 1995
    Assignee: The Chromaline Corporation
    Inventors: Ron Couture, Todd R. Murphy, Toshifumi Komatsu
  • Patent number: 5403694
    Abstract: The present invention provides an imaging element comprising on a support in the order given, a hydrophilic layer containing a hydrophilic (co)polymer or (co)polymer mixture and being hardened with a hydrolyzed tetraalkyl orthosilicate crosslinking agent and a light sensitive layer containing a diazo resin or a diazonium salt characterized in that an intermediate hydrophilic layer containing an organic compound having one or more cationic groups is provided between said hydrophilic layer and said light-sensitive layer. There is further provided a method for making such an imaging element and a method for making a lithographic printing plate therewith.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: April 4, 1995
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Joan Vermeersch, Dirk Kokkelenberg, Guido Hauquier
  • Patent number: 5397675
    Abstract: The present invention provides a photosensitive resin composition for lithographic printing, which is developable with an alkali developer and exhibits excellent resolusion and excellent print durability. The photosensitive resin composition comprises (a) an alkali-swellable or alkali-soluble binder resin and (b) an oil-soluble diazo resin, wherein the binder resin has an acid value of 5 to 150 and has in molecules a group represented by ##STR1## wherein R.sup.1 represents a phenyl group which may have a substitution, R.sup.2 and R.sup.3, the same or different, represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.4 represents an alkylene group of which a backbone may be interrupted with an oxygen atom, a cycloalkylene group or a combination thereof, and may have thereon an alkyl group, a hydroxyl group, an oxo (.dbd.O) group or a combination thereof, and a and b independently shows 0 or 1.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 14, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Seuji Arimatsu, Katsuji Konishi, Yoshifumi Ichinose, Takakazu Hase