And Monomeric Processing Ingredient Patents (Class 430/196)
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Patent number: 5219700Abstract: A photosensitive composition comprising (a) a 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound, (b) alkali-soluble resin, (c) a halomethyloxadiazole compound which releases halogen free radicals by irradiation with actinic rays and (a) a dye which interacts withthe decomposition product of said halomethyloxydiazole compound and discolors or develops color. The composition exhibits excellent development latitude, light safety, visible-on-exposure characteristic and printing resistance.Type: GrantFiled: March 24, 1992Date of Patent: June 15, 1993Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
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Patent number: 5206110Abstract: A negative-working, radiation-sensitive composition comprising an admixture in a solvent of:(a) at least one cyclized rubber polymer,(b) at least one photoactive compound, and(c) an effective contrast enhancing amount of at least one rubber-soluble azo dye containing a reactive acrylate or methacrylate group of formula (I): ##STR1## wherein Q is a reactive group of the structure ##STR2## wherein Y is either H or CH.sub.3 ; wherein R.sub.1 is either H, CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 CH.sub.2 CN, CH CH.sub.2 OH or Q;wherein R.sub.2 is either H, CH.sub.3, OCH.sub.3, or NHCOCH.sub.3 ;wherein R.sub.3 is either H, OCH.sub.3 or OC.sub.2 H.sub.5 ; andwherein X is selected from the group consisting of an unsubstituted or a substituted benzene, thiazole, thiophene, benzothiazole, benzoisothiazole, thiadiazole, and pyrazole moiety having, if substituted, 1-3 substituent groups selected from cyano, nitro, acetyl, and halogen groups; the amount of said cyclized rubber being about 90% to 99.Type: GrantFiled: February 4, 1991Date of Patent: April 27, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Stephen F. Marcotte, Jr., John Griffiths
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Patent number: 5190845Abstract: A photosensitive resin composition comprising:(a) a polymer dyeable with an anionic dye(b) an azide photosensitive compound, and(c) a compound having at least two acryloyl and/or methacryloyl groups in the same molecule thereof, and a color filter obtained by using the resin composition.Type: GrantFiled: May 8, 1989Date of Patent: March 2, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Matsuo Hashimoto, Nobuyuki Futamura, Sumio Yoda, Yoshifumi Saiki
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Patent number: 5130224Abstract: A positive-working photoresist composition is disclosed comprising an alkali-soluble resin and a 1,2-naphthoquinonediazido group-containing compound, and further contains at least one light absorber selected from the group consisting of the azo compounds represented by the following formulae (I), (II), (III), (IV), (V) and (VI) in a proportion of from about 0.1 to about 10% by weight based on the total solid content of the photoresist composition, and is useful for forming a fine pattern of excellent quality even on a substrate with unevenness or high reflectivity: ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group; and X represents a sulfur atom or an oxygen atom; ##STR2## wherein R.sub.2 represents a hydroxyl group or a di(lower alkyl)amino group; R.sub.3 and R.sub.4 each represents a hydrogen atom or a carboxyl group, provided that at least one of R.sub.3 and R.sub.4 represents a carboxyl group; and R.sub.Type: GrantFiled: February 28, 1990Date of Patent: July 14, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Tadayoshi Kokubo
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Patent number: 5066567Abstract: A positive-working photosensitive composition is disclosed that comprises a photosensitive compound which is either of the o-quinone diazide type or comprises a photolytic acid donor in combination with a compound containing a C-O-C group, a binder which is soluble or swellable in an aqueous-alkaline solution and a dye of the general formula I ##STR1## The photosensitive composition of the present invention has a higher photosensitivity than comparable compositions containing other dyes.Type: GrantFiled: March 28, 1990Date of Patent: November 19, 1991Assignee: Hoechst AktiengesellschaftInventors: Hans-Joachim Merrem, Gerhard Buhr, Ruediger Lenz
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Patent number: 5049477Abstract: A radiation responsive composition containing a compound represented by the following formula (I) and a photoreducing agent capable of forming a redox couple together with said compound for many uses, e.g., image formation, etching, plating, etc.: ##STR1## wherein N represents a nitrogen atom; X represents an oxygen atom (--O--), a sulfur atom (--S--), or a nitrogen-containing group of formula, ##STR2## R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents a mere bond, a substituted or unsubstituted alkyl, aryl, heterocyclic, acyl, aralkyl, alkenyl, alkynyl or carbamoyl group, or a sulfonyl group into which a substituted or unsubstituted alkyl or aryl group has been introduced, provided that at least one of the substituents R.sup.1 to R.sup.3 be a substituted or unsubstituted aryl or heterocyclic group and that two or more of R.sup.1, R.sup.2 and R.sup.3, or of R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: April 14, 1989Date of Patent: September 17, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Koki Nakamura, Masayoshi Tsuboi, Keizo Koya
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Patent number: 5041570Abstract: A photosensitive agent comprising an aromatic diazide compound represented by Formula (I) ##STR1## wherein X denotes ##STR2## Y denotes --CH.dbd.CH--, ##STR3## R.sub.1 is --CH.sub.2 CH.sub.2 --, R.sub.2 --CH.sub.2 CH.sub.3, R.sub.3 is hydrogen, m is 1, and n is 1,R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are individually hydrogen, alkyl, substituted alkyl, aryl, or two of R.sub.6 to R.sub.9 form alkylene groups, provided that R.sub.6 to R.sub.9 are not all hydrogen simultaneouslyand use of the photosensitive agent in a photosensitive composition and in a method forming forming an image.Type: GrantFiled: July 31, 1989Date of Patent: August 20, 1991Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Noriaki Tochizawa, Hideo Kikuchi
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Patent number: 4954418Abstract: A photoresist film containing a phosphate of a formalin condensate of diazodiphenylamine, 2.5-bis(4'-azide-2'-sulphobenzilidene) cyclopentanone Na, polyvinylalcohol, and polyvinylpyrrolidone is formed on the inner surface of a faceplate. The photoresist film is hardened by light exposure using a point or linear light source, which is essentially a circular light source, via a shadow mask having a large number of apertures. A light absorbing film is formed on this photoresist film. Then the hardened photoresist film and the light absorbing film on top of it are removed using a peeling agent.Type: GrantFiled: May 31, 1989Date of Patent: September 4, 1990Assignee: Kabushiki Kaisha ToshibaInventor: Norio Koike
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Patent number: 4927732Abstract: A positive-working photosensitive composition is disclosed that comprises a photosensitive compound which is either of the o-quinone diazide type or comprises a photolytic acid donor in combination with a compound containing a C--O--C group, a binder which is soluble or swellable in an aqueous-alkaline solution and a dye of the general formula I ##STR1## The photosensitive composition of the present invention has a higher photosensitivity than comparable compositions containing other dyes.Type: GrantFiled: October 20, 1988Date of Patent: May 22, 1990Assignee: Hoechst AktiengesellschaftInventors: Hans-Joachim Merrem, Gerhard Buhr, Ruediger Lenz
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Patent number: 4910119Abstract: New polymers comprising repeat units represented by the formula ##STR1## where R is a hydrogen or a halogen atom, a cyanide group or an alkyl group,R1, R2 and R3 are identical or different, and each denotes a hydrogen or a halogen atom, an alkyl group, an alkoxy group or an alkoxycarbonyl group,R4 is a hydrogen atom or a divalent radical,A denotes the atoms required for completing a mononuclear or dinuclear aromatic ring system andm is 2 or 3,are used as binders in positive-working, radiation-sensitive recording materials.Type: GrantFiled: September 15, 1988Date of Patent: March 20, 1990Assignee: Hoechst AktiengesellschaftInventors: Arnold Schneller, Juergen Sander
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Patent number: 4877714Abstract: A photosensitive resin composition which comprises as an essential component a resin emulsion comprising resin particles, which do not make coalescence to form a continuous film when the resin emulsion is applied on a substrate and dried, obtained by subjecting a polymerizable composition comprising at least one polymerizable vinyl monomer and at least one of a photo-reactive compound and a photo-initiator dissolved therein to emulsion polymerization.Type: GrantFiled: August 25, 1988Date of Patent: October 31, 1989Assignee: Nippon Paint CompanyInventors: Tahahiro Tsunoda, Tsuguo Yamaoka, Seiji Arimatsu
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Patent number: 4859562Abstract: A photosensitive mixture that contains a photosensitive compound, for example, a photoinitiator or a diazo compound, and a reaction product of a polymer containing active hydrogen with an olefinically unsaturated compound represented by the formula ##STR1## wherein X and Y are the same or different and denote oxygen or sulfur,R.sub.1 is an olefinically unsaturated aliphatic radical containing 2 to 8 carbon atoms andR.sub.2 is a saturated aliphatic radical containing 1 to 8 carbon atoms or an aryl radical containing 6 to 10 carbon atoms,is suitable for producing photoresists and printing plates.Type: GrantFiled: May 8, 1987Date of Patent: August 22, 1989Assignee: Hoechst AktiengesellschaftInventors: Georg Pawlowski, Hans-Jerg Kleiner, Thomas Gerdau
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Patent number: 4840869Abstract: Light sensitive compositions are disclosed which comprise 2-halomethyl-1,3,4,-oxadiazole compounds having a heterocyclic radical in the fifth position containing at least one element selected from the group consisting of oxygen, nitrogen, sulphur, and selenium directly or through a vinyl radical.Type: GrantFiled: August 10, 1987Date of Patent: June 20, 1989Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Noriyasu Kita, Kiyoshi Goto
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Patent number: 4839254Abstract: A photosensitive mixture contains a photosensitive compound and a polymeric binder which s a reaction product of a compound represented by the formula ##STR1## wherein X and Y are the same or different, and each denotes oxygen or sulfur,R.sub.1 and R.sub.2 are the same or different, and each denotes an unsubstituted or substituted alkyl, cycloalkyl or alkoxy radical containing from 1 to 6 carbon atoms; an unsubstituted or substituted aryl or aryloxy radical containing from 6 to 10 carbon atoms; or, together with the phosphorus atom, a 5- or 6-membered heterocyclic ring which is unsubstituted or substituted or which carries a fused benzene ring,with a polymer containing active hydrogen. The novel binders used in the mixture can be easily prepared and yield photosensitive layers of good developability and developer resistance.Type: GrantFiled: May 8, 1987Date of Patent: June 13, 1989Assignee: Hoechst AktiengesellschaftInventors: Georg Pawlowski, Hans-Jerg Kleiner
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Patent number: 4822719Abstract: A radiation-sensitive mixture which contains(A) a polymer comprised of repeat units represented by the formula ##STR1## where R is a hydrogen or a halogen atom, a cyanide group or an alkyl group of 1-4 carbon atoms,R.sup.1, R.sup.2 are identical or different, and eachand R.sup.3 denotes a hydrogen or a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an acyl group, an aryloxy group, an aroyl group or aralkyl group,R.sup.4 is a hydrogen atom or a divalent organic group which is linked to another unit represented by formula (I),X denotes an oxygen atom or one of the groups NR.sup.8, OCH.sub.2 CHOHCH.sub.2 OCO, OCH.sub.2 CH.sub.2 O and OCH.sub.2 CH.sub.2 OCO, where R.sup.Type: GrantFiled: August 13, 1986Date of Patent: April 18, 1989Assignee: Hoechst AktiengesellschaftInventors: Arnold Schneller, Ralf Schulze, Ju Sander, Kurt Erbes
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Patent number: 4797348Abstract: A dually photosensitive composition useful as a photoresist in the manufacture of ICs and the like electronic devices, which is positively photosensitive by exposure to ultraviolet in a relatively small dose but negatively photosensitive by exposure to ultraviolet in a substantially larger dose than above or by exposure to far ultraviolet light, is obtained by admixing a positive-type photoresist material comprising a novolac resin and an o-naphthoquinone diazide compound with a bisazide compound such as 4,4'-diazidodiphenyl sulfide. The inventive photosensitive composition provides a possibility of developing an ingenious technique for patterning of a photoresist layer on the substrate such as a checkboard-like patterned layer by use of a photomask of a line-and-space pattern.Type: GrantFiled: February 17, 1988Date of Patent: January 10, 1989Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoichi Nakamura, Shirushi Yamamoto, Takashi Komine, Akira Yokota, Hisashi Nakane
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Patent number: 4792516Abstract: A photosensitive composition comprising (a) a photosensitive component such as an aromatic diazo compound or an aromatic azide, (b) a polymer and (c) a quaternary alkylammonium salt wherein each straight- or branched-chain alkyl group has 1 to 7 carbon atoms is suitable for producing a positive type or negative type photresist excellent in contrast and sensitivity in the microlithography of semiconductor elements.Type: GrantFiled: January 5, 1987Date of Patent: December 20, 1988Assignee: Hitachi Chemical CompanyInventors: Minoru Toriumi, Hiroshi Shiraishi, Ryotaro Irie, Shigeru Koibuchi
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Patent number: 4783391Abstract: A radiation-sensitive composition is described, which is comprised of (1) a polymer containing repeating units of the formula: ##STR1## wherein R.sup.1 is a trivalent or tetravalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.2 is a divalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.3 is hydrogen or an ammonium ion, n is 1 or 2, and COOR.sup.3 is located in an ortho or peri position with respect to the amide linkage, (2) an organic compound having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) an aromatic monoazide compound [III] having no substituent or having a neutral or acidic substituent. This composition has a highly improved radiation sensitivity and the sensitive wavelength region of this composition is very broad. This composition can give a highly heat-resistant relief pattern with a good edge sharpness.Type: GrantFiled: November 25, 1986Date of Patent: November 8, 1988Assignee: Toray Industries, Inc.Inventors: Gentaro Ohbayashi, Susumu Umemoto, Hiroo Hiramoto
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Patent number: 4772534Abstract: A light-sensitive composition containing a novel light-sensitive s-triazine compound represented by the formula (I) as a free radical-generating agent is disclosed. The s-triazine compound responds radiation in the range of the near ultraviolet to visible light, shows high sensitivity for photolysis and, therefore, the compositon has high light-sensitivity.Type: GrantFiled: September 5, 1986Date of Patent: September 20, 1988Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Hirokazu Kondo, Yoshimasa Aotani
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Patent number: 4762767Abstract: New aminoazobenzene derivatives of the general formula I ##STR1## in which R and R' independently of one another denote hydrogen, alkyl with up to 4 C atoms or halogen,X denotes hydrogen or O--Y andY denotes alkyl or acyl with in each case up to 4 C atoms or optionally substituted aryl with up to 10 C atoms,are outstandingly suitable as radiation-absorbing substances in negatively operating photoresist compositions.Type: GrantFiled: April 30, 1986Date of Patent: August 9, 1988Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Gunther Haas, Karl H. Neisius
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Patent number: 4711603Abstract: A concrete slab which has settled is stabilized and may even be lifted by forcing a pier through the slab and into the underlying soil and then attaching the pier at its upper end to the slab. To this end a vertical hole is drilled through the slab as is a smaller oblique hole, with the latter intersecting and passing through the former. Then a jacking unit is attached to the upper surface of the slab around the vertical hole. The jacking unit forces a succession pier sections through the vertical hole and into the underlying soil, with these sections being fitted together end-to-end to form a pier. In time significant resistance is encountered, and at this point, while the jacking unit exerts a downwardly directed force on the pier and an upwardly directed counterforce on the slab, a hole is drilled through the portion of the pier that is within the slab, this being done by using the oblique hole in the slab as a guide for the drill bit.Type: GrantFiled: February 25, 1985Date of Patent: December 8, 1987Assignee: Magnum Piering, Inc.Inventors: Dondeville M. Rippe, Jr., David T. Scaturro
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Patent number: 4707430Abstract: Disclosed herein is an optical recording medium which includes a recording layer composed of (a) an organometallic complex having an absorption maximum in the wavelength range of 600-1200 nm, (b) a resinous binder and (c) a sensitizer capable of generating radicals upon exposure to ultraviolet rays. The recording of information on the recording layer is effected with ease by exposure to ultraviolet rays. The reproduction of recorded information is effected by a laser beam having an oscillatory wavelength in the visible or near infrared wavelength range.Type: GrantFiled: February 26, 1986Date of Patent: November 17, 1987Inventors: Hiroshi Ozawa, Yoichi Hosono, Sumio Hirose, Katsuyoshi Sasagawa, Masao Imai
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Patent number: 4702992Abstract: The undercoating composition of the invention, useful for providing an undercoating layer for a top coat of a photosensitive resist layer on a substrate surface, comprises, as a principal ingredient thereof, a condensation product obtained by the condensation reaction between a hydroxy-substituted diphenylamine and a melamine compound substituted on the nitrogen atoms with methylol groups and/or alkoxymethyl groups. The undercoating obtained of the composition is highly resistant against the attack by the overcoating solution applied thereon so that the fidelity of the pattern reproduction by the photolithographic technique is greatly improved by virtue of the absence of any disorder at the interface between the undercoating and top coat layers. The advantage is further increased when the undercoating composition further comprises a photoextinctive agent, e.g. a dye, having absorptivity in the wave length region where the photosensitive resist of the top coat has sensitivity.Type: GrantFiled: March 6, 1985Date of Patent: October 27, 1987Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Wataru Ishii, Shozo Miyazawa, Shinji Tsuchiya, Hisashi Nakane, Akira Yokota
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Patent number: 4701399Abstract: A photosensitive composition containing a 2-halomethyl-5-substituted-1,3,4-oxadiazole compound represented by the following general formula (I): ##STR1## wherein A represents a substituted or unsubstituted aromatic residue; X represents a hydrogen atom, a cyano group, an alkyl group or an aryl group; Y represents a chlorine atom or a bromine atom; and n represents an integer of 1 to 3.The free radical generating agent represented by the general formula (I) has a photosensitive wavelength range from near ultraviolet range to visible range, high photo-decomposition sensitivity and good compatibility with other components present in the photosensitive composition.The photosensitive composition is suitable for use in light-sensitive printing plates or photo-resists.Type: GrantFiled: February 25, 1985Date of Patent: October 20, 1987Assignee: Fuji Photo Film Co., Ltd.Inventors: Teruo Nagano, Tadao Toyama, Akira Nagashima
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Patent number: 4701300Abstract: Photoresist formulations for forming relief structures from highly heat-resistant polyimide polymers, containing in an organic solvent in essence at least(a) one polyamide ester prepolymer carrying photopolymerizable radicals(b) a radiation-reactive copolymerizable unsaturated compound(c) a photosensitizer(d) a photoinitiator(e) a leuco dye, exhibit enhanced photosensitivity if they contain as the photoinitiator a compound of the type of the N-azidosulphonylarylmaleimides and as leuco dye a compound of the type of the triarylmethanes.Type: GrantFiled: January 15, 1986Date of Patent: October 20, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Hans J. Merrem, Rudolf Klug, Thomas Herold
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Patent number: 4698291Abstract: 4'-Azidobenzal-2-methoxyacetophenone is an excellent photosensitive compound and can give a photosensitive composition together with an alkaline-aqueous-solution-soluble polymer which can be insolubilized in an alkaline aqueous solution by photochemical curing with 4'-azidobenzal-2-methoxyacetophenone, and if necessary together with an organic solvent, said composition showing a very small change in viscosity with the lapse of long time.Type: GrantFiled: July 17, 1986Date of Patent: October 6, 1987Assignees: Hitachi Chemical Co., Ltd., Hitachi, Ltd.Inventors: Shigeru Koibuchi, Asao Isobe, Daisuke Makino
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Patent number: 4656116Abstract: Polyimides of aromatic tetracarboxylic acid derivatives and aromatic diamines where both ortho-positions relative to a phenylene radical bonded to an imide group of the polymer are substituted by alkyl groups can be radiation-crosslinked with organic chromophoric polyazides. Solutions of said polyimides and polyazides in organic solvents can be used as radiation-sensitive coating compositions for, for example, preparing insulating and protective films and in particular for producing printed circuits and integrated circuits.Type: GrantFiled: October 4, 1984Date of Patent: April 7, 1987Assignee: Ciba-Geigy CorporationInventors: Ottmar Rohde, Josef Pfeifer
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Patent number: 4654292Abstract: A photoresist composition comprising a conjugated diene polymer or its cyclized product, a photocuring agent soluble in an organic solvent and a pyrazole compound having a skeleton represented by the following formula. ##STR1## Also provided is a method of forming a photoresist pattern using the aforesaid composition.Type: GrantFiled: September 17, 1985Date of Patent: March 31, 1987Assignees: Nippon Zeon Co., Ltd., Fujitsu LimitedInventors: Masayuki Oie, Satoshi Ogawa, Sadao Sugimoto, Masahiro Yamazaki, Katsuhiro Fujino
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Patent number: 4640885Abstract: The present invention discloses a method of photolytically developing a colored image on a cellulosic material. In this method, the material is contacted with a nitrogen containing polymer in solution and a mono-sulfonyl azide compound in solution. The sample is thereafter exposed to a UV-containing light source for an amount of time sufficient to develop a color thereon.Type: GrantFiled: June 28, 1985Date of Patent: February 3, 1987Assignee: Armstrong World Industries, Inc.Inventors: Ronald S. Lenox, Anne L. Schwartz, Charles E. Hoyle
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Patent number: 4608333Abstract: A radiation-sensitive composition is described, which is comprised of (1) a polymer containing repeating units of the formula: ##STR1## wherein R.sup.1 is a trivalent or tetravalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.2 is a divalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.3 is hydrogen or an ammonium ion, n is 1 or 2, and COOR.sup.3 is located in an ortho or peri position with respect to the amide linkage, (2) an organic compound having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) an aromatic secondary or tertiary amine compound which is chemically inactive to actinic radiation. This composition has an improved photo-sensitivity or radiation sensitivity and can give highly heat-resistant relief patterns with a good edge sharpness and good mechanical and chemical properties as well as good insulating properties.Type: GrantFiled: February 10, 1984Date of Patent: August 26, 1986Assignee: Toray Industries, Inc.Inventors: Gentaro Ohbayashi, Susumu Umemoto, Hiroo Hiramoto
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Patent number: 4598036Abstract: A print-out composition containing a leuco dye and a photooxidizing agent is described, said print-out composition containing at least one carbazomethane compound represented by formula (I) as the leuco dye ##STR1## wherein Y represents an amino group-substituted phenyl group represented by formula (Ia) ##STR2## or an indolyl group represented by formula (Ib) ##STR3## wherein X.sub.1 and X.sub.2 each represents a hydrogen atom, an unsubstituted alkyl group, or an alkyl group substituted by a halogen atom, a hydroxy group, a cyano group, or a lower alkoxy group, said alkyl group having up to 12 carbon atoms, a cycloalkyl group, a phenyl group, a benzyl group, or a phenyl or benzyl group substituted by a halogen atom, a lower alkyl group, or a lower alkoxy group, or said X.sub.1 and X.sub.2 together may form a 5-membered or 6-membered heterocyclic group together with the nitrogen atom bonded thereto; X.sub.Type: GrantFiled: September 10, 1984Date of Patent: July 1, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Sadao Ishige
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Patent number: 4596755Abstract: A photoresist composition, comprising, a water-soluble azide compound and a water-soluble polymer in combination with a water-soluble silane compound having at least two alkoxysilane groups.Type: GrantFiled: January 14, 1985Date of Patent: June 24, 1986Assignee: Kabushiki Kaisha ToshibaInventors: Norio Koike, Hatsuo Tsukagoshi
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Patent number: 4587197Abstract: A photosensitive polymer composition comprising (A) a poly(amic acid), (B) a compound or a mixture of compounds which can form a compound having two or more amino groups in the molecule, and (C) at least one compound having a boiling point of 150.degree. C. or higher at atmospheric pressure and selected from the group consisting of ##STR1## wherein R.sup.a, R.sup.b, R.sup.c, m and n are as defined in the specification, has good properties and does not produce cracks on a pattern at the time of development obtained from said composition.Type: GrantFiled: February 8, 1984Date of Patent: May 6, 1986Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.Inventors: Mithumasa Kojima, Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono
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Patent number: 4578341Abstract: A relief image-forming composition having an acidic pH comprises a photosensitive component and an indicator capable of existing in two states differing in actinic opacity dependent upon pH. A relief image is formed by (1) exposing to light selected areas of a layer of the composition, the indicator being in its state of lower actinic opacity, (2) removing layer material from the exposed areas or from the unexposed areas and (3) shifting the pH in the remaining layer material to a value at which the indicator exists in its state of higher actinic opacity. The resultant image can then be used as an intermediate original in diazotype copying processes.Type: GrantFiled: August 3, 1984Date of Patent: March 25, 1986Assignee: Sensitisers (Research) Ltd.Inventors: Peter B. Readings, Nandor Mihalik, Robin Taylor
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Patent number: 4565767Abstract: A light-sensitive polymer composition comprising a poly(amic acid), a special bisazide compound and an amine compound can give a film which has high sensitivity and in which portions exposed to light are not easily released by a developing solution at the time of development.Type: GrantFiled: April 24, 1984Date of Patent: January 21, 1986Assignees: Hitachi, Ltd, Hitachi Chemical Company, Ltd.Inventors: Fumio Kataoka, Fusaji Shoji, Isao Obara, Issei Takemoto, Hitoshi Yokono, Tokio Isogai, Mitsumasa Kojima
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Patent number: 4526854Abstract: A method for forming a pattern of a non-light-emitting black material on the inner surface of a faceplate of a color cathode ray tube is provided, which comprises the steps of forming a photoresist layer of a photoresist containing a water-soluble bisazidocompound, a water-soluble diazocompound, and a water-soluble polymeric material, on an inner surface of a faceplate of a color cathode ray tube, selectively exposing parts of the photoresist layer using a shadow mask so as to photocure the exposed parts, developing the photoresist layer to remove unexposed parts of the photoresist layer, thereby forming dots of the photoresist, forming a film of a non-light-emitting black material on the inner surface of the faceplate including the dots, and removing the dots and the non-light-emitting black material on the dots so as to form holes in the film of the non-light-emitting black material.Type: GrantFiled: February 18, 1983Date of Patent: July 2, 1985Assignee: Tokyo Shibaura Denki Kabushiki KaishaInventors: Shingo Watanabe, Takeo Itou
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Patent number: 4504567Abstract: The invention provides a light-sensitive lithographic printing plate containing a light-sensitive composition which has a different degree of solubility in an exposed area of said printing plate than in an unexposed area of said printing plate when said printing plate is developed in a developing solution. This printing plate is produced by a process which comprises coating on a support a solution prepared by dissolving a light-sensitive composition containing a light-sensitive material and at least one fluorinated surfactant having Formula (I) in a quantity of between 0.005% by weight and 0.05% by weight based on the weight of said composition, in at least one solvent having (A) a solubility parameter of at least 8(cal/cm.sup.3)1/2, and (B) a boiling point within the range of from 100.degree. to 200.degree. C. Said Formula (I) is Rf-A-Y, wherein Rf is a partially or completely fluorinated hydrophobic alkyl moiety, A is a single bind or bivalent moiety and Y is a hydrophilic moiety.Type: GrantFiled: August 9, 1984Date of Patent: March 12, 1985Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Takeshi Yamamoto, Kiyoshi Goto
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Patent number: 4501806Abstract: A method for forming a pattern of a non-light-emitting black material on the inner surface of a faceplate of a color cathode ray tube is provided, which comprises the steps of:forming a photoresist layer of a photoresist containing a water-soluble bisazidocompound, a water-soluble diazocompound, and a water-soluble polymeric material, on an inner surface of a faceplate of a color cathode ray tube;selectively exposing parts of the photoresist layer using a shadow mask so as to photocure the exposed parts;developing the photoresist layer to remove unexposed parts of the photoresist layer, thereby forming dots of the photoresist;forming a film of a non-light-emitting black material on the inner surface of the faceplate including the dots; andremoving the dots and the non-light-emitting black material on the dots so as to form holes in the film of the non-light-emitting black material.Type: GrantFiled: September 1, 1982Date of Patent: February 26, 1985Assignee: Tokyo Shibaura Denki Kabushiki KaishaInventors: Shingo Watanabe, Takeo Itou
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Patent number: 4500629Abstract: Images are prepared by a process in which a layer, supported on a substrate, of a liquid composition comprising(a) an anaerobically polymerizable material and(b) a photopolymerizable material is maintained in a substantially oxygen-free environment such that the composition solidifies. It is then exposed imagewise to actinic radiation and treated with a developer to remove parts of the layer which have not been struck by the radiation.The anaerobically polymerizable and photopolymerizable materials may be a mixture of two or more materials having these different functions, such as an acrylate ester with an azido compound, or the two functions may be combined in a single molecule. The products are suitable for use in producing printing plates and printed circuits.Type: GrantFiled: July 25, 1983Date of Patent: February 19, 1985Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Terence J. Smith
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Patent number: 4491629Abstract: Photoresist compositions based upon a water-soluble polymer are disclosed together with a water-soluble bisazide compound as a cross-linker, a water-soluble adhesion-improving diazo compound are characterized in that a water-soluble silane compound is included. The compositions are photosensitive, particularly to ultraviolet rays, and adhere well to the substrates to which they are applied. The compositions of the invention are used as photoresists.Type: GrantFiled: February 18, 1983Date of Patent: January 1, 1985Assignee: Tokyo Shibaura Denki Kabushiki KaishaInventors: Norio Koike, Takeo Ito, Shingo Watanabe, Kunihiro Ikari
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Patent number: 4451550Abstract: Novel, coatable, highly long-chain branched, ungelled, most preferably endblocked, non-linear phenoxy resins of random structure devoid of regularly recurring units, with the average distance between the branch sites thereof being essentially of the same order of magnitude as the average branch length, such resins advantageously comprising the copolymerization product of:(i) at least one dihydric phenol, e.g., sulfonyl diphenol;(ii) an epoxy comonomer having two epoxy functional groups, e.g., resorcinol diglycidyl ether;(iii) a branching agent comprising an epoxy or phenolic compound having a functionality greater than 2, and preferably at least 3, wherein the amount of branching agent is sufficient to provide at least 10 mole percent branch sites in the polymer resin, and, most preferably;(iv) a monofunctional phenol or epoxide as an endblocker compound.The branched phenoxy resins are well adapted as matrices for enhanced film speed vesicular films.Type: GrantFiled: July 29, 1982Date of Patent: May 29, 1984Assignee: James River Graphics, Inc.Inventors: Everett W. Bennett, Ahmad Arfaei
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Patent number: 4391894Abstract: A method for preparing a substantially uniformily dyed photosensitive composition useful in the reprographic arts, and compositions useful therefor. A water soluble basic dye is reacted with an organic acid, or an ammonium or alkali metal salt thereof which is preferably monofunctional and the reaction product is substantially uniformly dissolved in a photosensitive diazo composition to impart the desired dye color thereto. The resultant dye colored photosensitive composition may then be coated upon a suitable support, for example, a film or metal sheet, to provide a photosensitized product useful in the reprographic arts, which possesses substantially uniform color characteristics and extended shelf life.Type: GrantFiled: August 28, 1981Date of Patent: July 5, 1983Assignee: Polychrome CorporationInventors: Ken-ichi Shimazu, Albert Deutsch
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Patent number: 4383903Abstract: A photo-curable resin composition is disclosed comprising (i) a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of the cyanate esters, coprepolymers of the cyanate esters and an amine and mixtures thereof, (b) at least one compound selected from the group consisting of monomers having at least one olefinically double bond prepolymers of the monomers, liquid rubbers having one or more acryloyl or methacryloyl groups and mixtures thereof and optionally (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides, coprepolymers of the maleimides and an amine and mixtures thereof and (ii) a photo polymerization initiator or a photo sensitizer.Type: GrantFiled: April 3, 1981Date of Patent: May 17, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Satoshi Ayano, Morio Gaku, Nobuyuki Ikeguchi, Hidenori Kinbara, Yasunari Osaki
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Patent number: 4363866Abstract: Process for forming a vesicular image utilizing a vesicular recording material having an imaging layer which includes a defined sulphone and/or sulphonamide additive in an amount of 1 to 100% by weight based upon the weight of a polymeric component of the plastics vehicle. The additive provides improved image density and a back-appearing image.Type: GrantFiled: April 14, 1981Date of Patent: December 14, 1982Assignee: Bedford LimitedInventors: Stuart C. Rennison, Ronald J. Stacey
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Patent number: 4356247Abstract: A light-sensitive composition particularly suitable for making light-sensitive lithographic printing plates is described composed of a mixture of a sensitizer and a photo-crosslinkable polymer, or a mixture of a sensitizer, a compound including a light-sensitive azido group and a polymer reactive with a decomposate of azido groups to be formed upon exposure to light, and a sensitizer represented by the formula (I) ##STR1## wherein A represents a non-metallic atomic group necessary for forming a heterocyclic ring containing nitrogen; R.sub.1 represents an alkyl group or a substituted alkyl group; R.sub.2 represents hydrogen, an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group; and Y and Z each represents an oxygen atom or a sulfur atom.Type: GrantFiled: October 27, 1980Date of Patent: October 26, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshimasa Aotani, Teruo Kojima, Eiji Nakakita
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Patent number: 4352878Abstract: When a low molecular weight dihydric or trihydric alcohol is added to a photoresist composition comprising a water-soluble polymer substance and a diazide photo-crosslinking agent, the fluidity of the composition is improved and the drying speed is moderately retarded and it enables the formation of a photoresist layer having a uniform film thickness and uniform drying degree. The said alcohol is exemplified by ethylene glycol, glycerol, etc. and is preferably added in an amount of 5-300 parts by weight per 100 parts by weight of the water-soluble polymer substance.Type: GrantFiled: October 6, 1980Date of Patent: October 5, 1982Assignee: Hitachi, Ltd.Inventors: Kiyoshi Miura, Naomitsu Watanabe, Yoshifumi Tomita
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Patent number: 4349619Abstract: By adding a compound represented by the following general formulas: ##STR1## to a conventional photoresist composition comprising a cyclized product of conjugated diene polymer or copolymer and a photo-crosslinking agent soluble in an organic solvent, an image having a high degree of resolution and only a small number of pinholes can be obtained even when a base board having a surface of a high reflectance is used.Type: GrantFiled: September 10, 1980Date of Patent: September 14, 1982Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoichi Kamoshida, Toshiaki Yoshihara, Yoshiyuki Harita, Kunihiro Harada
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Patent number: 4332874Abstract: Disclosed are a photosensitive composition comprising a copolymer comprising acrylamide, diacetone-acrylamide and a sulfonated vinyl monomer, such as sodium p-styrenesulfonate, and a water-soluble aromatic bisazide compound, and a pattern-forming method using this photosensitive composition.This photosensitive composition has a reciprocity law failure, and when this photosensitive composition is used, the development after light exposure is completed in a short time.Type: GrantFiled: October 24, 1980Date of Patent: June 1, 1982Assignee: Hitachi, Ltd.Inventors: Nobuaki Hayashi, Motoo Akagi, Kiyoshi Miura, Yoshiyuki Odaka
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Patent number: 4306014Abstract: A photo-sensitive and heat-sensitive composition consisting essentially of a leuco-pigment; a hydrogen donator; a photo-reductant which, when exposed to a visible light, produces a reducing agent by the action of said hydrogen donator coexisting therewith; a photooxidant which, when exposed to an ultraviolet ray, causes said leuco-pigment coexisting therewith to generate color and simultaneously, when reacted with said reducing agent, is deprived of its own oxidizing ability; and a cobalt complex which reacts with the reducing agent in amplifying manner to thereby suppress the reaction of a color-forming system, and a recording element using the same.Type: GrantFiled: March 31, 1980Date of Patent: December 15, 1981Assignee: Ricoh Co., Ltd.Inventors: Makoto Kunikane, Akiyoshi Yasumori, Kiyoshi Taniguchi, Tetu Yamamuro
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Patent number: 4287289Abstract: A novel photoresist composition is proposed which is very advantageously employed in the photoetching process for the manufacture of various kinds of electronic devices such as transistors, ICs, LSIs and the like. The photoresist composition of the invention comprises a cyclized rubber as the base component and a specified azobenzene compound as a photoextinction agent for preventing halation in the exposure of the photoresist films to ultraviolet light. The advantages of the inventive photoresist composition over the conventional ones are obtained in the remarkable stability of the halation preventing effect even after a prebaking treatment of the photoresist films at an elevated temperature to remove the solvent from the photoresist films applied on to the substrate surfaces owing to the unexpectedly small sublimation of the azobenzene compound contained in the photoresist films.Type: GrantFiled: June 19, 1979Date of Patent: September 1, 1981Assignee: Tokyo Ohka Kogyo Kabushiki KaishaInventor: Takayuki Sato