Patents Examined by John S. Y. Chu
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Patent number: 5547812Abstract: Microbridge formation in chemically amplified negative tone photoresists based on poly(hydroxystyrene) (PHS) is avoided when the PHS is blended together with a co-polymer of PHS and an acrylic polymer such as poly(methyl methacrylate) (PMMA). The blend should include at least 10% by weight of the co-polymer. In operation, hydrogen bonding between the hydroxystyrene sub-units and the methacrylate sub-units decreases the availability of sites for crosslinking, and this reduction in crosslinking sites makes the blend less susceptible to formation of polymer resist microbridges. The invention is practicable with a polymers having a wide range of molecular weights (2000-50000 daltons), and development can be achieved using the industry standard 2.38 wt % trimethylammonium hydroxide (TMAH) developer without any adverse impact on the photoresist.Type: GrantFiled: June 5, 1995Date of Patent: August 20, 1996Assignee: International Business Machines CorporationInventors: James P. Collins, Judy Dorn, James T. Fahey, Leo Linehan, William J. Miller, Wayne Moreau, Erik A. Puttlitz, Randolph Smith, Gary Spinillo
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Patent number: 5547534Abstract: A binary image comprising a plurality of first areas, at which a porous or particulate image-forming substance is adhered to a substrate, and a plurality of second areas, at which the substrate is free from the image-forming substance, is protected by laminating thereto a laminating sheet comprising a barrier layer, a durable layer and a support layer with the barrier layer facing the image, so that the barrier and durable layers adhere to both the first and second areas of the image. The support layer is then displaced away from the image such that the barrier and durable layers remain attached to the image. Both the barrier and durable layers are substantially transparent and the barrier layer comprises a polymeric organic material substantially impervious to the passage of hexane, isopropanol or water.Type: GrantFiled: September 9, 1993Date of Patent: August 20, 1996Assignee: Polaroid CorporationInventors: Robert M. Conforti, Sun-Wook Kim, Being-Kung Yao
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O-quinonediazide sulfonic acid esters of phenolic compounds and their use in forming positive images
Patent number: 5547814Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.Type: GrantFiled: May 26, 1995Date of Patent: August 20, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros -
Patent number: 5543261Abstract: The present invention provides an imaging element comprising on a hydrophilic support a light sensitive layer containing a diazo resin or a diazonium salt characterized in that said light sensitive layer contains pullulan. The obtained imaging element shows an improved storage stability.Type: GrantFiled: June 29, 1994Date of Patent: August 6, 1996Assignee: AGFA-Gevaert, N.V.Inventors: Joan Vermeersch, Guido Hauquier, Dirk Kokkelenberg
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Patent number: 5541033Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a positive photoresist composition and process for forming patterned image. Further the invention is drawn to a positive photoresist composition comprising an alkali-soluble resin and quinone diazide sulfonic acid triesters and diesters characterized by their HPLC peak areas.Type: GrantFiled: February 1, 1995Date of Patent: July 30, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
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Patent number: 5541035Abstract: A method of forming a multicolored image wherein image layers etc. formed on photosensitive transfer sheets are transferred in turn onto an image-receiving sheet and then, its image layer etc. are retransferred onto a permanent supporter. Both of a transferring image layer alone and a transferring image layer and adhesive layer are used properly for photosensitive transfer sheets. The finish quality comes close to original print and the runnability becomes better when making a color proof.Type: GrantFiled: May 18, 1994Date of Patent: July 30, 1996Assignee: Nippon Paper Industries Co., Ltd.Inventors: Hisahiro Omote, Satoshi Kuwabara, Masahide Takano
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Patent number: 5538832Abstract: A developing solution comprising a specific amount of a quaternary ammonium hydroxide represented by the general formula [(R.sup.1).sub.3 N--R].sup.+ .multidot.OH.sup.- (R indicates an alkyl group having 1 to 3 carbon atoms or a hydroxy-substituted alkyl group having 1 to 3 carbon atoms, and R.sup.1 indicates an alkyl group having 1 to 3 carbon atoms) and, if necessary, a quaternary ammonium hydrogen carbonate represented by the general formula [(R.sup.1).sub.3 N--R].sup.+ .multidot.HCO.sub.3.sup.- (R and R.sup.1 are the same as the above) and having a pH in the range of 9 to 13, and a process for producing printed circuit boards using an organic alkali solution, are provided. The developing solution needs no defoaming agent because it causes little foaming. Printed circuit boards produced by using the developing solution have excellent finished accuracy. Therefore, fine circuits of printed circuit networks can be produced with stability.Type: GrantFiled: December 1, 1994Date of Patent: July 23, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tetsuo Aoyama, Takeshi Nagasaka, Toshihiko Kobayashi, Naohito Yoshimura, Takashi Nakata, Youichi Takizawa
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Patent number: 5536619Abstract: The present invention provides a heat mode recording material comprising on a transparent support a recording layer containing a light to heat converting substance, an image forming substance and a binder characterised in that there is present a heat decomposable intermediate layer between said transparent support and said recording layer and said heat decomposable intermediate layer being contiguous to said recording layer. High density images practically free of fog are obtained. The images are suitable for use as masks in contact exposures of lithographic printing plate precursors.Type: GrantFiled: September 30, 1994Date of Patent: July 16, 1996Assignee: AGFA-Gevaert, N.V.Inventor: Yves Verburgh
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Patent number: 5534382Abstract: Disclosed is a positive photoresist composition comprising an alkali-soluble resin and the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonate acid ester of a polyhydroxy compound represented by formula (I): ##STR1## wherein R.sub.1 to R.sub.3 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, or an alkoxy group; and m, n and o each represent an integer of from 1 to 3. The photoresist composition has a high resolving power and a less layer thickness reliance of the resolving power, and a wide development latitude, is reluctant to form a development residue, and further has a very excellent storage stability, and does not deposit the photosensitive material and does not form microgels, i.e., shows no increase in the particles, with the passage of time.Type: GrantFiled: March 27, 1995Date of Patent: July 9, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Kenichiro Sato
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Patent number: 5534381Abstract: 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: GrantFiled: July 6, 1995Date of Patent: July 9, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: M. Zaki Ali, Mahfuza B. Ali
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Patent number: 5534384Abstract: A photosensitive material for the production of color proofing films for multicolor printing, having(A) a transparent, flexible film support of plastic,(B) a photopolymerizable layer which contains(B1) a polymeric binder,(B2) a free-radically polymerizable compound,(B3) a compound which is capable of initiating the polymerization of (B2) on exposure to actinic light, and(B4) a dye or a colored pigment in a primary color of multicolor printing, and(C) a thermoplastic adhesive layer having a layer weight of from about 2 to about 30 g/m.sup.2 on the photo-sensitive layer, wherein the thermoplastic adhesive layer contains from about 0.01 to about 0.5% by weight of a colorless pigment having a mean particle size which corresponds to from 1 to 100% of the layer thickness.Type: GrantFiled: February 19, 1993Date of Patent: July 9, 1996Assignee: Hoechst AktiengesellschaftInventors: Stephan J. W. Platzer, Siegfried Nuernberger, Karin Maerz
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Patent number: 5532105Abstract: A photolithographically viahole-forming photosensitive element is formed of a light-transmitting base material and a photosensitive resin composition laminated as a layer on the light-transmitting base material. The photosensitive resin composition comprises:(a) 100 parts by weight of a mixture comprising:(a-1) 10 to 90 parts by weight of a rubber,(a-2) 5 to 40 parts by weight of a phenol resin, and(a-3) 10 to 80 parts by weight of an epoxy resin;(b) 1 to 10 parts by weight of an epoxy resin photoinitiator; and(c) 1 to 10 parts by weight of an aromatic polyazide compound.Type: GrantFiled: August 9, 1993Date of Patent: July 2, 1996Assignee: Hitachi Chemical Company, Ltd.Inventors: Takashi Yamadera, Kazumasa Takeuchi, Ritsuko Obata, Naoki Fukutomi, Kazuko Suzuki
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Patent number: 5532116Abstract: An aqueous alkaline developing solution comprises an alkali compound, water and an alkylnaphthalene sulfonate having the following formula: ##STR1## in which R represents an alkyl group of 3 to 5 carbon atoms and q is 0 or an integer of 1 to 3, in the amount of 1 to 20 weight %. The aqueous alkaline developing solution further contains an anionic surface active agent of the specific sulfonate compound having a naphthalene ring and a polypolyoxyethylene moiety, in the amount of 0.1 to 10 weight % and an nonionic surface active agent having a polyoxyethylene moiety and an aromatic ring in its structure in the amount of 0.03 to 3 weight %, or contains an anionic surface active agent of the specific sulfonate compound having the specific aralkyl-substituted benzene ring and a polypolyoxyethylene moiety.Type: GrantFiled: February 25, 1994Date of Patent: July 2, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Tamotsu Suzuki, Mikio Totsuka, Chiyomi Niitsu, Fumiaki Shinozaki
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Patent number: 5532107Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and a photosensitive agent, characterized in that the positive resist composition contains, as the photosensitive agent, the quinonediazide sulfonate of at least one of phenolic compounds represented by the following general formulae (I) and (II): ##STR1## wherein R.sub.1 through R.sub.4 mean individually a hydrogen or halogen atom, a hydroxyl group, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.5 denotes a hydrogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or an aryl group with the proviso that the number of hydroxyl groups is 3 or 4; and ##STR2## wherein R.sub.6 through R.sub.9 mean individually a hydrogen or halogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.Type: GrantFiled: April 13, 1994Date of Patent: July 2, 1996Assignee: Nippon Zeon Co., Ltd.Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
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Patent number: 5529879Abstract: This invention relates to a photosensitive sheet having on a substrate one or more resin layers that are peelable from the substrate and heat-fusible, and a colored photosensitive layer in this order, said substrate comprising a biaxially stretched plastic film and having a molecular orientation ratio in the range of from 1.0 to 1.4.The object of this invention is to solve the problem of misregister without decreasing productivity during the formation of plastic film (substrate) or during the production of a photosensitive sheet in a method in which said photosensitive sheet having an image formed thereon and an image receiving sheet for receiving the image are superimposed on each other, and pressed and heated for image transfer.Type: GrantFiled: March 31, 1993Date of Patent: June 25, 1996Assignee: Nippon Paper Industries Co., Ltd.Inventors: Mitsuhide Hoshino, Fukuo Murata, Norio Yabe, Masahide Takano
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Patent number: 5529882Abstract: The present invention provides a positive type photosensitive anionic electrocoating composition having excellent running stability and highly reliable image formability, and a process for pattern formation using said composition. Said composition comprises, as essential components, a resin (A) containing polyethylene glycol or polypropylene glycol chains each having a substituted or unsubstituted phenyl group at the end and a compound (B) containing at least one quinone diazide sulfone unit, and contains carboxyl groups in an amount of 0.2-3 moles per kg (solid content) of the composition.Type: GrantFiled: April 17, 1995Date of Patent: June 25, 1996Assignee: Kansai Paint Co., Ltd.Inventors: Koji Takezoe, Noboru Nakai, Kenji Seko
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Patent number: 5529880Abstract: A photoresist that is a mixture of the esterification product of an o-quinonediazide compound and a novolak resin and a high molecular weight phenol having from 2 to 5 phenolic groups and at least 4 diazo naphthoquinone groups. The extent of esterification of the novolak resin is up to 20 percent of the hydroxyl groups and the degree of esterification of the phenol is at least 50 percent of the phenolic hydroxyl groups. The preferred novolak resins are the aromatic novolak resin that are the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde, each alone or in the presence of a reactive phenol.Type: GrantFiled: March 29, 1995Date of Patent: June 25, 1996Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Peter Trefonas, III
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Patent number: 5529881Abstract: A positive photoresist composition for super fine working is disclosed, which comprises (a) an alkali-soluble resin and (b) as a photosensitive compound the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid ester of a polyhydroxy compound represented by formula (I) or (II), wherein in a high-speed liquid chromatography measured using a ultraviolet ray of 254 nm, the pattern of the diester component and the pattern of the complete ester component of said 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid of the polyhydroxy compound shown by formula (I) or (II) are at least 50% and less than 40%, respectively, of the whole pattern areas; ##STR1## wherein R.sub.1 to R.sub.11, which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group, and R.sub.12 to R.sub.Type: GrantFiled: March 16, 1995Date of Patent: June 25, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Kenichiro Sato, Toshiaki Aoai, Kazuya Uenishi
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Patent number: 5525454Abstract: A photosensitive transfer material is disclosed including a temporary substrate having provided thereon an alkali-soluble thermoplastic resin layer, an intermediate layer, and a photosensitive resin layer in this order, the transfer material having an interlaminar adhesion which is lowest between the thermoplastic resin layer and the temporary substrate, wherein the alkali-soluble thermoplastic resin layer contains (A) an alkali-soluble thermoplastic resin having a weight average molecular weight of from 50,000 to 500,000 and a glass transition temperature of from 0.degree. to 140.degree. C. and (B) an alkali-soluble thermoplastic resin layer having a weight average molecular weight of from 3,000 to 30,000 and a glass transition temperature of from 30.degree. to 170.degree. C. at an (A)/(B) weight ratio of from 5/95 to 95/5. The transfer material can be transferred to a permanent substrate at a high speed without entrapping air bubbles due to unevenness on the permanent substrate.Type: GrantFiled: July 8, 1994Date of Patent: June 11, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Sadao Fujikura, Minoru Wada
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Patent number: 5518864Abstract: Disclosed is a photosensitive resin composition, containing a polyamic acid derivative having a repeating unit represented by general formula (1) given below and a photosensitive agent: ##STR1## where, R.sup.1 represents a tetravalent organic group, R.sup.2 represents a divalent organic group, and R.sup.3 and R.sup.4 represent a monovalent organic group, at least one of R.sup.3 and R.sup.4 being an organic group having at least on hydroxyl group bonded to an aromatic ring. A semiconductor substrate is coated with the photosensitive resin composition, followed by exposing the coated film to light through a patterning mask and subsequently applying a development and a heat treatment so as to form a polyimide film pattern. A baking treatment also be applied immediately after the exposure step. The photosensitive resin composition of the present invention performs the function of a positive or negative photoresist film and the function of a polyimide protective film on a semiconductor substrate.Type: GrantFiled: March 30, 1994Date of Patent: May 21, 1996Assignee: Kabushiki Kaisha ToshibaInventors: Masayuki Oba, Rumiko Hayase, Naoko Kihara, Shuzi Hayase, Yukihiro Mikogami, Yoshihiko Nakano, Naohiko Oyasato, Shigeru Matake, Kei Takano