Nitrogen Containing Compound Patents (Class 522/57)
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Patent number: 6713524Abstract: The invention relates to novel reactive polymers of formula wherein the variables are as defined in the claims. The polymers of the invention are useful for the modification of material surfaces and are particularly suitable for providing biomedical articles such as contact lenses with a hydrophilic coating.Type: GrantFiled: March 9, 2001Date of Patent: March 30, 2004Assignee: Novartis AGInventors: Jörg Leukel, Peter Chabrecek, Dieter Lohmann
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Patent number: 6624211Abstract: The present invention provides a dental material that includes a hardenable resin system and a first initiator system capable of hardening the hardenable resin.Type: GrantFiled: May 16, 2001Date of Patent: September 23, 2003Assignee: 3M Innovative Properties CompanyInventors: Naimul Karim, Joel D. Oxman, Ahmed S. Abuelyaman, Babu N. Gaddam
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Patent number: 6569603Abstract: There are disclosed a light-sensitive composition which comprises (A) a polymer having a phenyl group substituted by a vinyl group at a side chain, (B) a photopolymerization initiator and (C) a sensitizer which sensitizes the photo-polymerization initiator, or a light-sensitive composition which comprises (A′) a polymer, the above-mentioned (B) and (C), and (D) a monomer having at least two phenyl groups each of which is substituted by a vinyl group in the molecule of the monomer; and a method of forming a relief image which comprises coating the light-sensitive composition as mentioned above on a support, exposing the composition by exposure or scanning exposure and developing the same to form a relief image on the support.Type: GrantFiled: January 30, 2001Date of Patent: May 27, 2003Assignee: Mitsubishi Paper Mills LimitedInventor: Akira Furukawa
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Patent number: 6548567Abstract: The invention relates to an ionic compound corresponding to the formula [R1X1(Z1)—Q−—X2(Z2)—R2]m Mm+ in which Mm+ is a cation of valency m, each of the groups Xi is S═Z3, S═Z4, P—R3 or P—R4; Q is N, CR5, CCN or CSO2R5, each of the groups Zi is ═O, ═NC≡N, ═C(C≡N)2, ═NS(═Z)2R6 or ═C[S(═Z)2R6]2, each of the groups Ri, is Y, YO—, YS—, Y2N— or F, Y represents a monovalent organic radical or alternatively Y is a repeating unit of a polymeric frame. The compounds are useful for producing ion conducting materials or electrolytes, as catalysts and for doping polymers.Type: GrantFiled: August 17, 2001Date of Patent: April 15, 2003Inventors: Michel Armand, Christophe Michot, Yurii Yagupolskii, Lev Yagupolskii, Andrej Bezdudny, Natalya Kondratenko
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Patent number: 6512020Abstract: Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g.Type: GrantFiled: March 28, 2001Date of Patent: January 28, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Toshikage Asakura, Hitoshi Yamato, Masaki Ohwa, Jean-Luc Birbaum, Kurt Dietliker, Junichi Tanabe
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Publication number: 20020183411Abstract: An optical fiber coating material is provided in the form of an electron beam-curable resin composition comprising a polyurethane having at least two ethylenically unsaturated groups, a reactive diluent, and a compound having both nitrogen and sulfur atoms. The optical fiber coating material is sufficiently EB curable to minimize the dependency of gel fraction and Young's modulus on an EB dose and to comply with the high-speed drawing of optical fiber. The coating material is cured with EB under specific conditions to achieve a sufficient degree of cure and uniform properties without adversely affecting the transmission loss of the optical fiber.Type: ApplicationFiled: April 25, 2002Publication date: December 5, 2002Inventors: Toshio Ohba, Nobuo Kawada, Masaya Ueno, Masatoshi Asano, Shigeru Konishi
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Patent number: 6489374Abstract: The invention relates to &agr;-ammonium alkenes, iminium alkenes and amidinium alkenes in the form of their tetraaryl- or triaryl-alkylborate salts that can be converted photochemically into amines, imines or amidines, and to a process for the preparation thereof. The invention relates also to compositions polymerisable or crosslinkable under basic conditions comprising such &agr;-ammonium alkenes, iminium alkenes or amidinium alkenes in the form of their tetra- or tri-arylalkylborate salts, to a method of carrying out photochemically induced, base-catalysed reactions, and to the use of such compounds as photoinitiators for base-catalysed reactions.Type: GrantFiled: February 16, 2001Date of Patent: December 3, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Gisèle Baudin, Sean Colm Turner, Allan Francis Cunningham
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Patent number: 6458864Abstract: Compounds with chain transfer groups of the formula I, II, III and IV wherein a is 1 or 2; Ar and Ar1 inter alia are phenyl; Ar2 inter alia is phenylene, these groups being unsubstituted or substituted; X is a direct bond, —O—, —S— or —N(R6)—; Y inter alia is hydrogen or C1-C12alkyl; M1 is —NR3R4 or —OH, or M1 is Ar when R1 and R2 are alkoxy, or aryloxy; R1 and R2 independently of one another e.g. are C1-C8alkyl; R3 and R4 for example are C1-C12alkyl, or together are C3-C7alkylene; R5 inter alia is C1-C6alkylene or a direct bond; R6 is for example hydrogen; and Z is a divalent radical, provided that at least one of the radicals Ar, Ar1, Ar2, R1, R2, R3, R4, R5 or Y is substituted by SH groups; are suitable for the thermal preparation of macrophotoinitiators which are polymerized photochemically to give block-copolymers.Type: GrantFiled: November 27, 2000Date of Patent: October 1, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Toshikage Asakura, Masaki Ohwa, Hitoshi Yamato, Asako Ito
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Patent number: 6340716Abstract: The invention relates to an ionic compound corresponding to the formula [R1X1(Z1)—Q−—X2(Z2)—R2]m Mm+ in which Mm+ is a cation of valency m, each of the groups Xi is S═Z3, S═Z4, P—R3 or P—R4; Q is N, CR5, CCN or CSO2R5, each of the groups Zi is ═O, ═NC≡N, ═C(C≡N)2, ═NS(═Z)2R6 or ═C[S(═Z)2R6]2, each of the groups Ri, is Y, YO—, YS—, Y2N— or F, Y represents a monovalent organic radical or alternatively Y is a repeating unit of a polymeric frame. The compounds are useful for producing ion conducting materials or electrolytes, as catalysts and for doping polymers.Type: GrantFiled: March 25, 1999Date of Patent: January 22, 2002Assignee: ACEP Inc.Inventors: Michel Armand, Christophe Michot, Yurii Yagupolskii, Lev Yagupolskii, Andrej Bezdudny, Natalya Kondratenko
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Publication number: 20010037037Abstract: The invention relates to the use of oximesulfonic acid esters of formula I 1Type: ApplicationFiled: January 8, 2001Publication date: November 1, 2001Inventors: Kurt Dietliker, Martin Kunz
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Patent number: 6277897Abstract: The present invention is directed to new, energy-efficient photoinitiators in the form of &agr;-amino enol ether compounds. The present invention is also directed to a method of generating reactive species, which includes exposing one or more photoinitiators to radiation to form one or more reactive species. Also described are methods of polymerizing unsaturated monomers, methods of curing an unsaturated oligomer/monomer mixture, and methods of laminating using the photoinitiators of the present invention.Type: GrantFiled: June 3, 1999Date of Patent: August 21, 2001Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 6242057Abstract: A method of generating reactive species which includes exposing a wavelength specific photoreactor composition to radiation, in which the wavelength specific photoreactor composition comprises one or more wavelength-specific sensitizers associated with one or more reactive species-generating photoinitiators. Also described are methods of polymerizing unsaturated monomers, methods of curing an unsaturated oligomer/monomer mixture, and methods of laminating.Type: GrantFiled: April 29, 1998Date of Patent: June 5, 2001Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John Gavin MacDonald
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Patent number: 6238840Abstract: A photosensitive resin composition comprising (A) a photosensitive resin having one or more carboxyl groups, (B) a special epoxy curing agent, and (C) a photopolymerization initiator is excellent in adhesiveness, heat resistance, resistance to PCT and developability and suitable as a solder resist composition.Type: GrantFiled: November 10, 1998Date of Patent: May 29, 2001Assignee: Hitachi Chemical Company, Ltd.Inventors: Takao Hirayama, Kuniaki Sato, Toshihiko Ito, Toshizumi Yoshino, Hiroaki Hirakura
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Patent number: 6156815Abstract: 1,2-Disulfones are particularly suitable as thermally and photochemically activatable latent acid catalysts for binder systems which contain at least one acid-curable component.Type: GrantFiled: June 10, 1999Date of Patent: December 5, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Ekkehard Bartmann, Jorg Ohngemach
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Patent number: 6150430Abstract: Described is a process for producing an adherent organic polymeric layer on organic polymeric substrates following the steps of (a) treating the surface of the polymeric substrate to provide reactive groups; (b) applying to the treated surface a polymerizable composition of a surface modifying amount of an organofunctional silane, a catalyzing amount of material which generates acid upon exposure to actinic radiation, and a solvating amount of solvent; (c) exposing the coated surface to an adhesion improving amount of actinic radiation; and (d) applying and curing a photochromic or non-photochromic polymer-forming composition on the coated surface. Also described are articles produced by the process.Type: GrantFiled: July 6, 1999Date of Patent: November 21, 2000Assignee: Transitions Optical, Inc.Inventors: Robert W. Walters, Kevin J. Stewart
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Patent number: 6140385Abstract: Novel substituted diaryl ketones, photopolymerization compositions including the compounds, and methods using the same are disclosed. Polymerization of compositions which include the compounds of the invention may be activated by irradiating the composition with ultraviolet light using conventional techniques and radiation sources to give greatly improved cure speeds. The compounds of the invention also show a significantly elevated level of reactivity at a narrow wavelength band, with a peak emission wavelength at or near 308 nm. Because of the increased level of activity, the photoinitiator can be used in considerably lower amounts.Type: GrantFiled: September 30, 1998Date of Patent: October 31, 2000Assignee: First Chemical CorporationInventors: Joseph Stanton Bowers, Jr., Rajamani Nagarajan, Charles Uriah Pittman, Jr., E. Sonny Jonsson
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Patent number: 6124371Abstract: The invention relates to a composition comprising polymerizable material and an anionic photocatalyst. The photocatalyst is a photolabile compound able to liberate a strong base having a pK.sub.a .gtoreq.12. The catalyst can be illustrated by the structural formula Z-A wherein Z is a photolabile group and A is a strong base, for example, a nitrogen containing compound such as, a secondary amine, a guanidine or amidine and Z is covalently bound to A.Type: GrantFiled: August 21, 1998Date of Patent: September 26, 2000Assignee: DSM N.V.Inventors: Dirk A. W. Stanssens, Johan F. G. A. Jansen
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Patent number: 6121340Abstract: The present invention relates to a photodefinable dielectric composition comprising a photoinitiator and a polycyclic addition polymer comprising polycyclic repeating units that contain pendant silyl functionalities containing hydrolyzable substituents. Upon exposure to a radiation source the photoinitiator catalyzes the hydrolysis of the hydrolyzable groups to effect the cure of the polymer and adhesion of the polymer to desired substrates.Type: GrantFiled: November 4, 1997Date of Patent: September 19, 2000Assignee: The B. F. Goodrich CompanyInventors: Robert A. Shick, Saikumar Jayaraman, Edmund Elce, Brian L. Goodall
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Patent number: 6103450Abstract: A photosensitive polymer, a dissolution inhibitor, and a chemically amplified photoresist composition containing the photosensitive polymer and the dissolution inhibitor are provided. The photosensitive polymer is a copolymer polymerized with 5-norbornene-2-methanol derivative monomer having a C.sub.1 to C.sub.20 aliphatic hydrocarbon as a side chain, and a maleic anhydride monomer. The dissolution inhibitor is a tricyclodecane derivative or a sarsasapogenin derivative, each having an acid-labile group as a functional group. The chemically amplified photoresist composition containing the photosensitive polymer and/or dissolution inhibitor has a strong resistance to etching and excellent adherence to underlying layer.Type: GrantFiled: March 26, 1999Date of Patent: August 15, 2000Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 6096483Abstract: The present invention provides a curable composition which comprises (A) a base-generating substance which generates a base when exposed to the action of ultraviolet light, (B) a siloxane polymer which has silicon-hydrogen bonds (Si--H) capable of reacting with hydroxy groups under the effect of the base to form silicon-oxygen bonds (Si--O) and hydrogen molecules (H.sub.2), and (C) an acid substance. This composition is cured by irradiation with ultraviolet light. During this ultraviolet irradiation, a mask is placed between a coating film of the composition and the radiation source, and the uncured portions of the composition are dissolved and removed so that a pattern is formed. The residual portions are then heated to produce a pattern-cured product.Type: GrantFiled: March 31, 1997Date of Patent: August 1, 2000Assignee: Dow Corning Asia, Ltd.Inventors: Brian R. Harkness, Mamoru Tachikawa, Kasumi Takei
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Patent number: 6057078Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: July 23, 1998Date of Patent: May 2, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 6051367Abstract: A photopolymerizable composition which comprises a compound having one or more addition-polymerizable ethylenically unsaturated bonds and a specific oxime ether compound. The photopolymerizable composition has high sensitivity to actinic rays in a wide region, ranging from ultraviolet to visible light, and gives a photosensitive material which has improved film strength in exposed areas.Type: GrantFiled: February 23, 1998Date of Patent: April 18, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Tatsuji Higashi
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Patent number: 5998099Abstract: A process for device fabrication and resist materials that are used in the process are disclosed. The resist material contains a substituted amine-containing component and a polymer. The substituted-amine containing component is either a photoacid generator, or an amine additive to the resist material that also contains a photoacid generator. The resist material contains acid labile groups either pendant to the polymer or to a dissolution inhibitor that is combined with the polymer. The acid labile groups significantly decrease the solubility of the polymer in a solution of aqueous base. A film of the resist material is formed on a substrate and exposed to delineating radiation. The radiation induces a chemical change in the resist material rendering the exposed resist material substantially more soluble in aqueous base solution than the unexposed portion of the resist material.Type: GrantFiled: May 22, 1998Date of Patent: December 7, 1999Assignee: Lucent Technologies Inc.Inventors: Francis Michael Houlihan, Omkaram Nalamasu, Thomas Ingolf Wallow
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Patent number: 5882835Abstract: A chemical amplified positive photoresist composition including a resin having the repeating unit of Formula I and a photoacid generator. The resin ranges, in polystyrene-reduced molecular weight, from about 2,000 to 1,000,000. In Formula I, k and l each represent a mole ratio satisfying the condition of k+l=l. R.sub.1 is a hydrogen atom or a methyl group. R.sub.2 and R.sub.3 are independently either a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R.sub.4 is an acetate group, a t-butoxycarbonyl group, a benzyl group, a trialkylsilyl group or an alkyl group. The photoacid generator which generates an acid by radiation.Type: GrantFiled: September 17, 1997Date of Patent: March 16, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ki-Dae Kim, Sun-Yi Park
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Patent number: 5852067Abstract: A near infrared rays-curing putty composition containing (A) a polymerizable ethylenically unsaturated group-containing resin, (B) a polymerizable ethylenically unsaturated compound and (C) a near infrared rays polymerization initiator, said near infrared rays polymerization initiator (C) being a near infrared rays-absorbing cationic dye and a resin powder consisting of gelation polymer fine particles.Type: GrantFiled: November 15, 1996Date of Patent: December 22, 1998Assignees: Showa Denko K. K., Kansai Paint Co., Ltd.Inventors: Hajime Sukejima, Shinji Tomita, Shuichi Sugita, Kazuhiko Ooga
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Patent number: 5849808Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.Type: GrantFiled: April 19, 1996Date of Patent: December 15, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Hans-Thomas Schacht, Norbert Muenzel
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Patent number: 5837746Abstract: Compounds of the formulaRG--A--INwherein IN is a photoinitiator basic structure A is a spacer group and RG is a functional reactive group can be employed as coreactive photoinitiators for photo-polymerization of systems containing ethylenically unsaturated compounds.Type: GrantFiled: June 23, 1997Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Manfred Kohler, Jorg Ohngemach, Eike Poetsch, Rudolf Eidenschink, Gerhard Greber, Dieter Dorsch, Jurgen Gehlhaus, Konrad Dorfner, Hans Ludwig Hirsch
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Patent number: 5807905Abstract: Compounds of the formula I ##STR1## in which n and o are a number from 0 to 50, m is a number from 1 to 50, u and v are 0 or 1, and at least one of the indices u and v is 1, R.sub.1, R.sub.2, R.sub.2a, R.sub.3 and R.sub.4 independently of one another are, for example, aromatic hydrocarbons, R.sub.5, if n and o are 0, is for example C.sub.1 -C.sub.12 alkyl and, if n and/or o are greater than 0, or if n and o are 0 and at the same time only one index u or v is 1, R.sub.5 may additionally, for example, be an aromatic hydrocarbon, at least one of the radicals R.sub.1, R.sub.2, R.sub.2a, R.sub.3, R.sub.4 and R.sub.5 being an aromatic hydrocarbon radical which is sterically hindered ortho to the boron atom, X is, for example, C.sub.1 -C.sub.20 alkylene, phenylene, biphenylene, etc., and Z is a radical which is able to form positive ions, are suitable as photoinitiators, both the compounds per se and their combination with dyes or other electron acceptors.Type: GrantFiled: November 21, 1996Date of Patent: September 15, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5800964Abstract: Disclosed is a novel and improved photoresist composition which comprises:(A) a film-forming resinous compound which is, in the presence of an acid, subject to a change in the solubility in an alkaline solution; and(B) an acid-generating agent capable of releasing an acid by the exposure to actinic rays which is an oxime sulfonate compound represented by the general formulaNC--CR.sup.1 .dbd.N--O--SO.sub.2 --R.sup.2,in which R.sup.1 and R.sup.2 are, each independently from the other, an unsubstituted or halogen-substituted monovalent aliphatic hydrocarbon group, e.g., alkyl, cycloalkyl, alkenyl and cycloalkenyl groups.Type: GrantFiled: September 24, 1996Date of Patent: September 1, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuru Sato, Kazuyuki Nitta, Hideo Hada, Tatsuya Hashiguchi, Hiroshi Komano, Toshimasa Nakayama
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Patent number: 5723511Abstract: A process for the preparation of branched thermoplastic resins comprising: heating a mixture of a free radical initiator, at least one first free radical reactive monomer, at least one free radical reactive branching agent compound, and at least one stable free radical agent, to produce a linear or unbranched polymer product with a free radical initator fragment at one end and a covalently bonded stable free radical agent at the other end of the polymerized chain of monomers; and irradiating the unbranched polymer product in the presence of a reactive compound selected from the group consisting of a free radical reactive monomer, a branching agent compound, and mixtures thereof to form a branched polymeric product.Type: GrantFiled: June 17, 1996Date of Patent: March 3, 1998Assignee: Xerox CorporationInventors: Peter M. Kazmaier, Barkev Keoshkerian, Karen A. Moffat, Michael K. Georges, Gordon K. Hamer, Richard P. N. Veregin
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Patent number: 5703140Abstract: A photopolymerizable composition is disclosed, comprising at least (i) a compound having an addition-polymerizable ethylenically unsaturated bond, and (ii) an oxime ether compound. The photopolymerizable composition of the present invention shows high sensitivity to active light rays over a wide range of from ultraviolet ray to visible light and at the same time, the photosensitive material using the photopolymerizable composition of the present invention is improved in the storage stability. Further, the development precipitate generated from the developer waste after development of the photosensitive material is restrained.Type: GrantFiled: January 23, 1996Date of Patent: December 30, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Syunichi Kondo
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Patent number: 5693452Abstract: A positive chemically amplified resist composition is disclosed, comprising (a) a compound which generates an acid upon irradiation with active light or radiant ray; (b) a resin insoluble in water but soluble in an aqueous alkali solution; and (c) a low molecular acid-decomposable dissolution inhibitor having a molecular weight of 3,000 or less and containing an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Also disclosed is a positive chemically amplified resist composition comprising the foregoing compound (a) and (d) a resin having an acid-decomposable alkyl ester group represented by formula (I), and which increases its solubility in an alkali developer by the action of an acid, and having a sodium content and a potassium content each of 30 ppb or less. Still further disclosed are methods for producing the compounds (c) and (d).Type: GrantFiled: October 26, 1995Date of Patent: December 2, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Toru Fujimori
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Patent number: 5691395Abstract: Radiation sensitive compositions, processes for using the compositions, and articles of manufacture comprising the compositions. The photoimageable compositions of the invention comprises a radiation sensitive component, a resin binder and a polybutadiene that comprises one or more internal epoxide groups. In preferred aspects, the compositions of the invention further comprise a crosslinking agent such as a melamine or an epoxidized material, or mixtures thereof.Type: GrantFiled: July 12, 1994Date of Patent: November 25, 1997Assignee: Shipley Company Inc.Inventors: Philip D. Knudsen, Charles R. Shipley, Daniel Y. Pai
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Patent number: 5629095Abstract: The present invention relates to radiation curable silicone vinyl ethers and methods for preparing silicone vinyl ethers. More particularly, the present invention relates compositions containing vinyl ether functional silicones and to the preparation and use of silicone vinyl ethers which are curable by addition of photocleavable acids and exposure to ultraviolet or electron beam radiation.Type: GrantFiled: May 18, 1995Date of Patent: May 13, 1997Assignee: Dow Corning CorporationInventors: Valerie J. Bujanowski, Shedric O. Glover, Susan V. Perz, Maris J. Ziemelis, Gary R. Homan, Michael W. Skinner
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Patent number: 5627011Abstract: The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituents;R.sub.0 is either a R.sub.1 --X group or R.sub.2 ;X is an oxygen or a sulfur atom;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, andR.sub.2 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: May 12, 1995Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventors: Norbert Munzel, Reinhard Schulz, Heinz Holzwarth, Stephan Ilg
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Method of making shaped dental articles via photoiniferter polymerization of the dental compositions
Patent number: 5449703Abstract: The present invention provides a novel dental composition and a method of making shaped dental articles therefrom via photoiniferter polymerization. The dental composition comprises acrylic photoiniferter block polymer, a monomer charge comprising free radically polymerizable acrylic monomer, and a filler and optionally includes pigments, sensitizers, medicaments, stabilizers, accelerators, etc. The dental composition is alternately exposed to a source of radiant energy and shaped in a desired manner in order to form a partially cured dental article. The partially cured dental article is then cured by a final exposure to the radiant energy source, providing a final cured article. The resultant reinforced acrylic copolymer system provides a shaped dental article which can be a denture base, a denture liner or a restorative.Type: GrantFiled: June 3, 1994Date of Patent: September 12, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Sumita B. Mitra, Mahfuza B. Ali -
Patent number: 5449588Abstract: A photosensitive resin composition containing 0.5 to 15 parts by weight of a compound generating an acid by light irradiation in 100 parts by weight of a polyamic acid amide having an alkoxysilane having a specified structure at its terminals are provided,which composition has superior resolution properties, a small shrinkage of volume, a superior adhesion onto a substrate, and can prepare a polyimide by baking.Type: GrantFiled: May 27, 1994Date of Patent: September 12, 1995Assignee: Chisso CorporationInventors: Hirotoshi Maeda, Eiji Watanabe, Kouichi Katou, Kouichi Kunimune
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Patent number: 5411995Abstract: Xanthate, dithiocarbamate and dithiophosphate salts of transition metals, together with a coinitiator selected from organic halogen and tertiary amine compounds provide light activated initiator systems for radically polymerizable ethylenically unsaturated compounds such as (meth)acrylate esters.Type: GrantFiled: April 8, 1993Date of Patent: May 2, 1995Assignee: Loctite CorporationInventor: Darchun B. Yang
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Patent number: 5403695Abstract: 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: GrantFiled: April 30, 1992Date of Patent: April 4, 1995Assignee: Kabushiki Kaisha ToshibaInventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Naohiko Oyasato, Yoshihito Kobayashi, Shuzi Hayase
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Patent number: 5376503Abstract: A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.Type: GrantFiled: November 24, 1992Date of Patent: December 27, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Jay D. Audett, Kenneth O. McElrath
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Patent number: 5356947Abstract: The present invention provides controllably curable photoiniferter containing adhesive compositions which are suitable for the mounting of microelectronic devices such as flip chips onto transparent wiring boards, a method of making the adhesive compositions, and a method of using the adhesive compositions in order to bond microelectronic devices to transparent wiring boards by intermittent exposure of the adhesive composition to a radiant energy source. The adhesive compositions can be cured in a stepwise fashion by intermittent controlled exposure to a source of radiation thus providing exactly the amount of cure and hardening desired.Type: GrantFiled: October 29, 1992Date of Patent: October 18, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Mahfuza B. Ali, Jean M. Pujol
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Patent number: 5318999Abstract: The present invention provides a novel dental composition and a method of making shaped dental articles therefrom via photoiniferter polymerization. The dental composition comprises acrylic photoiniferter block polymer, a monomer charge comprising free radically polymerizable acrylic monomer, and a filler and optionally includes pigments, sensitizers, medicaments, stabilizers, accelerators, etc. The dental composition is alternately exposed to a source of radiant energy and shaped in a desired manner in order to form a partially cured dental article. The partially cured dental article is then cured by a final exposure to the radiant energy source, providing a final cured article. The resultant reinforced acrylic copolymer system provides a shaped dental article which can be a denture base, a denture liner or a restorative.Type: GrantFiled: October 8, 1991Date of Patent: June 7, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventors: Sumita B. Mitra, Mahfuza B. Ali
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Patent number: 5314962Abstract: An acrylate is polymerized by the photo-decomposition of ##STR1## to make a polymeric intermediate containing dithiocarbamate groups at both its ends, and a hard polymer-forming monomer is polymerized by the photo-decomposition of this dithiocarbamate group-containing polymeric intermediate to form blocks of a polymer of said hard polymer-forming monomer on both sides of said polymeric intermediate, thereby forming an ABA type block copolymer.Type: GrantFiled: June 29, 1993Date of Patent: May 24, 1994Assignee: Mitsubishi Petrochemical Company LimitedInventors: Takayuki Otsu, Shunichi Himori, Takashi Kiriyama
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Patent number: 5298532Abstract: The invention relates to an accelerated photoiniferter polymerization method which involves the addition of a polymerization accelerating amount of a at least one metal compound accelerator during the photoiniferter polymerization process.Preferably, the metal compound or compounds used are represented by the general formula M.sub.x L.sub.z whereinM is a cation having a valency of z of a metal which is selected from the group consisting of tin, zinc, cobalt, titanium, palladium, and lead;x is an integer of at least 1;L is an anion having a valency of x which is selected from the group consisting of C.sub.1-20 alkyl, --aryl, --OR, ##STR1## NO.sub.3.sup.-, SO.sub.4.sup.-, and PO.sub.4.sup.-3 ; R is selected from the group consisting C.sub.1-20 alkyl and aryl; andz is an integer of at least 1.Most preferably, the metal compound is selected from the group consisting of stannous 2-ethylhexanoate, zinc 2-ethylhexanoate and mixtures thereof.Type: GrantFiled: February 28, 1992Date of Patent: March 29, 1994Assignee: Minnesota Mining and Manufacturing CompanyInventor: Mahfuza B. Ali
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Patent number: 5240972Abstract: The present invention relates to an iniferter compound of the formula I(T).sub.n wherein I represents the free radical initiator portion of the iniferter compound and wherein I comprises a hydroxy-functional polyurethane polymer which comprises: (i) a polyurethane backbone; (ii) a plurality of cross-linkable hydroxy groups pendant from the polyurethane backbone, wherein the polyurethane backbone has a hydroxy equivalent weight of from about 500 to about 10,000; (iii) at least n organic groups X which can be the same or different pendant from the polyurethane backbone wherein each organic group X is also bonded to a T group; T represents the terminator portion of the iniferter; and n is an integer of at least 1; wherein T and X are organic groups selected so that the T--X bond is capable of dissociating upon being subjected to an appropriate energy source of forming a terminator free radical of the formula nT.multidot. and an initiator free radical of the formula I(.multidot.).sub.n .Type: GrantFiled: April 30, 1992Date of Patent: August 31, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ramesh C. Kumar, Takatoshi Ohkubo
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Patent number: 5238782Abstract: A photopolymerizable composition comprises at least one addition polymerizable compound having at least one ethylenically unsaturated bond and at least one photopolymerization initiator represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.4 independently represent hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, hydroxyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted amino group with the proviso that R.sub.1 to R.sub.4 may form a non-metallic ring together with the carbon atoms bonded thereto; R.sub.5 and R.sub.6 each represents hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a heteroaromatic group, an acyl group, cyano group, an alkoxycarbonyl group, carboxyl group or a substituted alkenyl group with the proviso that R.sub.5 and R.sub.Type: GrantFiled: February 26, 1990Date of Patent: August 24, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Mitsuru Koike
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Patent number: 5236967Abstract: An optical molding composition is used for casting and does not cause irritation to the skin or possess a bad smell. This composition comprises1. an actinic radiation-curable, radical-polymerizable organic compound comprising(1) one or more polythiol compounds and(2) one or more polyene compounds each having at least two actinic radiation-reactive carbon-to-carbon double bonds in the molecule, and2. an actinic radiation-sensitive radical polymerization initiator.Type: GrantFiled: February 18, 1992Date of Patent: August 17, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuo Ohkawa, Seiichi Saito
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Patent number: 5230984Abstract: A resin composition comprising (A) a copolymer obtained by copolymerizing (a) acrylic acid and/or methacrylic acid, (b) at least one compound having an unstable group against an acid such as t-amyl acrylate, t-amyl methacrylate, etc. and (c) a copolymerizable monomer such as n-butyl acrylate and (B) a photoacid generator is effective for providing an electro-deposition bath good in water dispersion stability and an electrodeposited film having high sensitivity and high resolution.Type: GrantFiled: November 29, 1991Date of Patent: July 27, 1993Assignee: Hitachi Chemical Company, Ltd.Inventors: Shigeo Tachiki, Masahiko Hiro, Toshihiko Akahori, Takuro Kato
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Patent number: 5200436Abstract: The present invention provides novel siloxane iniferter compounds, block copolymers made therewith, and a method of making the block copolymers. The siloxane iniferter compounds can be represented by the formula ##STR1## wherein T and X are organic groups selected so that the T-X bond is capable of dissociating upon being subjected to an appropriate energy source to form a terminator free radical of the formula T.multidot. and an initiator free radical;R.sub.1, R.sub.2, R.sub.5 and R.sub.6 are monovalent moieties selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and aryl which can be the same or are different;R.sub.3 and R.sub.4 are monovalent moieties which can be the same or different selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.Type: GrantFiled: July 25, 1991Date of Patent: April 6, 1993Assignee: Minnesota Mining and Manufacture CompanyInventors: Ramesh C. Kumar, Milton H. Andrus, Jr., Miecyzslaw H. Mazurek
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Patent number: 5190989Abstract: An AB-type block copolymer represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrocarbon group having 1 to 10 carbon atoms; R.sup.2 represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms; R.sup.3 represents a benzyl group, ##STR2## wherein R.sup.4 represents an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 18 carbon atoms; M represents a group represented by the formula (M.sup.2).sub.m --(M.sup.1).sub.n or (M.sup.1).sub.m --(M.sup.2).sub.n, each of m and n being a natural number of 20 to 5000; is prepared by a process of first polymerizing either a monomer for forming the M.sup.1 block or a monomer for forming the M.sup.2 block in the presence of a sulfur-containing compound having formula (XIII): ##STR3## wherein R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: November 30, 1990Date of Patent: March 2, 1993Assignee: Mitsubishi Petrochemical Company LimitedInventor: Shunichi Himori