From Fused Or Bridged Ring Containing Monomer Patents (Class 526/280)
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Patent number: 11943997Abstract: Provided are: a highly durable polymer having a high hole-injection/transport capacity; and a composition for an organic electroluminescent element, which contains the polymer.Type: GrantFiled: September 16, 2020Date of Patent: March 26, 2024Assignee: Mitsubishi Chemical CorporationInventors: Yanjun Li, Tomokazu Umemoto, Hideki Gorohmaru, Koichiro Iida, Kouji Adachi
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Patent number: 11932726Abstract: The instant disclosure provides (among other things) improved methods of preparing fluorenyl-based polymeric reagents, methods of recovering and purifying such polymeric reagents, methods of reducing unwanted impurities in a fluorenyl-based polymeric reagent, fluorenyl-based polymeric reagents prepared by the methods described herein, and conjugates prepared by reaction with fluorenyl-based polymeric reagents prepared by the methods described herein.Type: GrantFiled: October 11, 2019Date of Patent: March 19, 2024Assignee: Nektar TherapeuticsInventors: Sean M. Culbertson, Samuel P. McManus, Antoni Kozlowski, Venkata Ravidnranadh Somu
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Patent number: 11639405Abstract: Embodiments in accordance with the present invention encompass compositions encompassing a procatalyst, a photoacid generator, a photosensitizer and one or more monomers which undergo vinyl addition polymerization when said composition is exposed to suitable UV irradiation and heated to a temperature from 50° C. to 100° C. to form a substantially transparent film. The monomers employed therein have a range of refractive index from 1.4 to 1.6 and thus these compositions can be tailored to form transparent films of varied refractive indices. Accordingly, compositions of this invention are useful in various opto-electronic applications, including as coatings, encapsulants, fillers, leveling agents, among others.Type: GrantFiled: May 29, 2020Date of Patent: May 2, 2023Assignee: PROMERUS, LLCInventor: Oleksandr Burtovyy
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Patent number: 11586111Abstract: A resist composition including a compound (D0) represented by general formula (d0) and a resin component (A1) has a structural unit (a0) in which a compound represented by general formula (a0-1) has a polymerizable group within the W1 portion converted into a main chain (in formula (d0), Rd01 represents a fluorine atom or a fluorinated alkyl group; In formula (a0-1), W1 represents a polymerizable group-containing group; Ct represents a tertiary carbon atom, and the ?-position of Ct is a carbon atom which constitutes a carbon-carbon unsaturated bond; R11 represents an aromatic hydrocarbon group; or a chain hydrocarbon group; R12 and R13 each independently represents a chain hydrocarbon group, or R12 and R13 are mutually bonded to form a cyclic group).Type: GrantFiled: December 2, 2019Date of Patent: February 21, 2023Assignee: TOKYO OHKA KOGYO CO., LTD.Inventors: Yasuhiro Yoshii, Masahito Yahagi, Yoichi Hori, Takahiro Kojima
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Patent number: 10273327Abstract: The present disclosure is directed to methods of making a polymer, including exposing a reaction mixture including a strained cyclic unsaturated monomer and an organic initiator to a stimulus to provide an activated organic initiator, whereby the activated organic initiator is effective to polymerize the strained cyclic unsaturated monomer via a 4-membered carbocyclic intermediate to provide a polymer having constitutional units derived from the strained cyclic unsaturated monomer.Type: GrantFiled: September 3, 2015Date of Patent: April 30, 2019Assignee: University of WashingtonInventors: Andrew J. Boydston, Kelli Ogawa, Adam E. Goetz, Damian Dunford, Laura Marie Murphy Pascual
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Patent number: 10263220Abstract: The manufacturing method for QLED display of the present invention uses the white QD layer to replace the organic light-emitting layer of the WOLED structure in the WOLED process, and adds the UV photoinitiator to the white QD layer. The QDs between the sub-pixels are irreversibly quenched by UV irradiation with mask to form fine QD pattern so as to eliminate the mutual influence between adjacent sub-pixels and effectively reduce the distance between two sub-pixels, increase the aperture ratio, and improve the color gamut and contrast of the display to enhance the color expression capability of the display. The manufacturing method is simple, and saves cost and process. Compared with the conventional TFT-LCD display, the QLED display of the present invention is not required to fabricate a liquid crystal cell separately, thinner and lighter, and has a longer lifetime and higher luminous efficiency than a conventional WOLED display.Type: GrantFiled: December 19, 2016Date of Patent: April 16, 2019Assignee: SHENZHEN CHINA STAR OPTOELECTRONICS TECHNOLOGY CO., LTD.Inventor: Guohe Liu
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Patent number: 10078261Abstract: Disclosed herein is a graft block copolymer comprising a first block polymer; the first block polymer comprising a backbone polymer and a first graft polymer; where the first graft polymer comprises a surface energy reducing moiety that comprises a halocarbon moiety, a silicon containing moiety, or a combination of a halocarbon moiety and a silicon containing moiety; a second block polymer; the second block polymer being covalently bonded to the first block; wherein the second block comprises the backbone polymer and a second graft polymer; where the second graft polymer comprises a functional group that is operative to undergo acid-catalyzed deprotection causing a change of solubility of the graft block copolymer in a developer solvent.Type: GrantFiled: September 6, 2013Date of Patent: September 18, 2018Assignees: ROHM AND HAAS ELECTRONIC MATERIALS LLC, THE TEXAS A&M UNIVERSITY SYSTEMInventors: Sangho Cho, Guorong Sun, Karen L. Wooley, James W. Thackeray, Peter Trefonas, III
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Patent number: 10030105Abstract: The invention relates to low molecular mass products and to the use thereof as reversible or permanent low-temperature crosslinkers in Diels-Alder reactions.Type: GrantFiled: June 29, 2012Date of Patent: July 24, 2018Assignee: Evonik Degussa GmbHInventors: Friedrich Georg Schmidt, Stefan Hilf, Emmanouil Spyrou, Jiawen Zhou, Nathalie Guimard, Christopher Barner-Kowollik, Kim Klaus Oehlenschlaeger, Andre Hennig
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Patent number: 9459376Abstract: An optical polymer satisfying an expression: (?A??B)/?B×100<60, where, ?A is the melt viscosity of the optical polymer measured at a temperature of 290° C. and a shear rate of 200 (l/s), and ?B is the melt viscosity of the optical polymer measured at a temperature of 290° C. and a shear rate of 2000 (l/s).Type: GrantFiled: December 17, 2013Date of Patent: October 4, 2016Assignee: ZEON CORPORATIONInventors: Ayumi Sato, Yosuke Harauchi, Hiroya Nishioka, Takashi Houkawa, Kenji Umeda, Takuya Komatsubara
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Patent number: 9279023Abstract: Process for polymerizing ethylene in a reactor system containing one or more reactors in series, having a characteristic such that the average polymerization productivity [kgPE/kgcata] per unit ethylene per hour a1 during operation at any first residence time r1 is less than 1.7 (a2r2?a1r1)/(r2?r1), where a2 is the average polymerization productivity [kgPE/kgcata] per unit ethylene per hour during operation at any second residence time r2 where r2>r1, a2 and r2 being measured either in the same reactor in the case of a single reactor polymerization, or in a reactor subsequent to the reactor in which a1 and r1 are measured in the case where the polymerization takes place in more than one reactor. The specific yield of the reactor system is greater than 0.3 tonnes/m3. Operating the system under the above conditions results in improved productivity/unit ethylene.Type: GrantFiled: June 21, 2012Date of Patent: March 8, 2016Assignee: INEOS EUROPE AGInventors: Daniel Marissal, Benoit Koch, Christophe Moineau
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Publication number: 20150147698Abstract: A negative resist composition comprising a polymer comprising recurring units (a) of formula (1) and having a Mw of 1,000-500,000 as base resin is provided. R1 is H or methyl, X is a single bond or —C(?O)—O—R4—, R2 is a single bond or C1-C4 alkylene, R3 is C2-C8 alkylene, R4 is a single bond or C1-C4 alkylene, and 0<a?1.0. The composition exhibits a high resolution due to controlled acid diffusion and forms a resist film which is unsusceptible to swell in the developer and hence to pattern collapse.Type: ApplicationFiled: November 25, 2014Publication date: May 28, 2015Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Masayoshi Sagehashi
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Publication number: 20150147697Abstract: A resist composition comprising a polymer comprising recurring units (a) of formula (1) and having a Mw of 1,000-500,000 as base resin is provided. R1 is H or methyl, X is a single bond or —C(?O)—O—R5—, R2 is a single bond or C1-C4 alkylene, R3 is C2-C8 alkylene, R4 is an acid labile group, R5 is a single bond or C1-C4 alkylene, and 0<a?1.0. The composition is of dual-tone type in that an intermediate dose region of resist film is dissolved in a developer, but unexposed and over-exposed regions of resist film are insoluble.Type: ApplicationFiled: November 25, 2014Publication date: May 28, 2015Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masayoshi Sagehashi
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Patent number: 9017918Abstract: A polymer is obtained from a hydroxyphenyl methacrylate monomer having an acid labile group substituted thereon. A positive resist composition comprising the polymer as a base resin has a very high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good profile and minimal line edge roughness of a pattern after exposure, a retarded acid diffusion rate, and good etching resistance.Type: GrantFiled: June 1, 2011Date of Patent: April 28, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Seiichiro Tachibana, Koji Hasegawa
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Publication number: 20150064626Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl and/or phenolic hydroxyl group substituted with an acid labile group and recurring units of tert-butyl or tert-amyl-substituted hydroxyphenyl methacrylate and having a weight average molecular weight of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.Type: ApplicationFiled: July 14, 2014Publication date: March 5, 2015Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Koji Hasegawa
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Publication number: 20150062518Abstract: A liquid crystal display device includes a substrate; a liquid crystal layer containing a liquid crystal material; and a first layer formed on the substrate, the first layer being configured to control the alignment of liquid crystal molecules, the first layer being placed between the substrate and the liquid crystal layer, and being formed by polymerization of two or more kinds of radical polymerizable monomers in the liquid crystal layer.Type: ApplicationFiled: April 24, 2013Publication date: March 5, 2015Inventors: Masanobu Mizusaki, Satoshi Enomoto
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Publication number: 20150057422Abstract: There are provided a radically polymerizable composition that has a low viscosity suitable for use in coating and that forms a cured product having a high refractive index, a cured product formed by curing the composition, and plastic lens formed by curing the composition. The radically polymerizable composition includes, as essential components, phenylbenzyl acrylate (A); and bis[(meth)acryloylmethyl]biphenyl (B) or biphenyl compound (C) having a molecular structure in which biphenyl structures are bonded to each other through a methylene.Type: ApplicationFiled: March 12, 2012Publication date: February 26, 2015Applicant: DIC CORPORATIONInventors: Akihiro Kondo, Atsuhisa Miyawaki, Nobuo Kobayashi, Naoya Ikushima, Kazuaki Hatsusaka
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Publication number: 20150030983Abstract: A resist top coat composition includes a polymer including a base resin having a repeating unit p of styrene having a 1,1,1,3,3,3-hexafluoro-2-propanol group and a repeating unit q of acenaphthylene having chemical formula 1. R is hydrogen, hydroxyl. R1 is hydrogen, hydroxyl, linear or branched C1-C10-alkyl, cycloalkyl, acyloxy, alkoxycarbonyl, carboxyl, —OC(?O)R2. R2 is linear or branched C1-C10-alkyl, cycloalkyl or fluorinated alkyl. m is 1 or 2. p and q are positive numbers satisfying the expressions 0<p<1.0 and 0<q<1.0, and 0<p+q?1.0.Type: ApplicationFiled: July 28, 2014Publication date: January 29, 2015Inventors: Jun HATAKEYAMA, Hyun-Woo KIM
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Publication number: 20150014894Abstract: Provided is a curable composition for imprints having good patternability and dry etching resistance. Disclosed is a curable composition for imprints comprising a polymerizable monomer (Ax) having a substituent having an aromatic group and having a molecular weight of 100 or more, and a photopolymerization initiator.Type: ApplicationFiled: October 2, 2014Publication date: January 15, 2015Applicant: FUJIFILM CORPORATIONInventors: Kunihiko KODAMA, Kyouhei SAKITA, Hiroyuki YONEZAWA
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Publication number: 20150018445Abstract: A curable resin composition comprising a (meth)acrylate monomer having an aromatic ring, a non-conjugated vinylidene group-containing compound represented by the general formula below, and a thermal or a photo-radical polymerization initiator makes it possible to produce a cured product with minimized occurrence of burring during molding and high product yield after molding. The cured product has good heat coloration resistance and low Abbe's number. R11, R12, R15, and R16 represent a substituent and A represents an atomic group necessary for forming a cyclic structure.Type: ApplicationFiled: September 26, 2014Publication date: January 15, 2015Applicant: FUJIFILM CORPORATIONInventors: Yuusuke IIZUKA, Tatsuhiko OBAYASHI, Naoyuki MOROOKA, Takayasu NAGAI, Ayumi SOMEYA
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Patent number: 8871884Abstract: The inventions disclosed, described, and/or claimed herein relate to copolymers comprising copolymers comprising electron accepting A subunits that comprise thiazolothiazole, benzobisthiazole, or benzobisoxazoles rings, and electron donating subunits that comprise certain heterocyclic groups. The copolymers are useful for manufacturing organic electronic devices, including transistors and solar cells. The invention also relates to certain synthetic precursors of the copolymers. Methods for making the copolymers and the derivative electronic devices are also described.Type: GrantFiled: October 26, 2010Date of Patent: October 28, 2014Assignee: University of WashingtonInventors: Samson A. Jenekhe, Selvam Subramaniyan, Eilaf Ahmed, Hao Xin, Felix Sunjoo Kim
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Patent number: 8853345Abstract: Provided is a copolymer. The copolymer, when incorporated into a resist composition, can provide a satisfactory resist pattern with high sensitivity, high resolution, high etching resistance and a reduced amount of outgas.Type: GrantFiled: December 20, 2011Date of Patent: October 7, 2014Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Jung-Hoon Oh, Joon Hee Han, Tae Gon Kim, Hyun Sang Joo
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Patent number: 8846833Abstract: The invention relates to a process for preparing pressure-sensitive adhesives (PSAs) which have high molar masses in combination with a narrow molar mass distribution, and also to PSAs, especially polyacrylate-based PSAs, prepared accordingly. It has been found that, surprisingly, polymers with high molar masses and a narrow molar mass distribution, more particularly polyacrylates with high molar masses and a narrow molar mass distribution, can be prepared outstandingly in particular by means of RAFT processes in the presence of a diradical initiator which undergoes thermal cyclization to form a diradical, these polymers being suitable for use as high-shear-strength PSAs.Type: GrantFiled: December 19, 2012Date of Patent: September 30, 2014Assignee: TESA SEInventor: Alexander Prenzel
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Patent number: 8808960Abstract: A compound represented by the formula (I): wherein R1 represents a hydrogen atom etc., R2 and R3 each independently represent a hydrogen atom etc., R4 represents a C1-C8 divalent hydrocarbon group, R5 represents a single bond etc., and R6 represents an unsubstituted or substituted C6-C20 aromatic hydrocarbon group, a polymer comprising a structural unit derived from the compound represented by the formula (I) and a chemically amplified positive resist composition comprising the polymer, at least one acid generator and at least one solvent.Type: GrantFiled: March 8, 2010Date of Patent: August 19, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Akita, Isao Yoshida, Kazuhiko Hashimoto
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Patent number: 8808966Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.Type: GrantFiled: July 25, 2012Date of Patent: August 19, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa
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Patent number: 8802798Abstract: A photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: wherein R1, R2, R3 and R5 are each a hydrogen atom or a methyl group; R4 is an acid-labile group or one of a specified subset of alicyclic hydrocarbon groups, alicyclic hydrocarbon groups, or hydrocarbon groups; R6 is a hydrogen atom or one of a specified subset of hydrocarbon groups or alicyclic hydrocarbon groups; x, y and z are optional values which meet x+y+z=1, 0<x?1, 0?y<1 and 0?z<1. Also disclosed is a resin having a (meth)acrylate unit of an alicyclic lactone structure represented by the formula (3): wherein R8 is a hydrogen atom or a methyl group, and R9 is one of a specified subset of hydrocarbon groups.Type: GrantFiled: August 29, 2008Date of Patent: August 12, 2014Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Publication number: 20140212810Abstract: A polymer comprising recurring units (a) of styrene having an HFA group and an ester group adjacent thereto and recurring units (b) having a hydroxyl group is used as base resin to formulate a negative resist composition. The negative resist composition has a high dissolution contrast in alkaline developer, high sensitivity, high resolution, good pattern profile after exposure, and a suppressed acid diffusion rate.Type: ApplicationFiled: December 23, 2013Publication date: July 31, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Koji Hasegawa, Daisuke Domon
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Patent number: 8785105Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.Type: GrantFiled: November 9, 2011Date of Patent: July 22, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 8778235Abstract: A colorant multimer includes, as a partial structure of a colorant moiety, a dipyrromethene metal complex compound or tautomer thereof obtained from: (i) a dipyrromethene compound represented by the following Formula (M); and (ii) a metal or a metal compound: wherein in Formula (M), R4, R5, R6, R7, R8, R9, and R10 each independently represent a hydrogen atom or a monovalent substituent.Type: GrantFiled: September 28, 2010Date of Patent: July 15, 2014Assignee: FUJIFILM CorporationInventors: Junichi Ito, Masaru Yoshikawa, Yuki Mizukawa, Kenta Ushijima, Shinichi Kanna, Haruki Inabe, Yoshihiko Fujie, Akiyoshi Goto, Yushi Kaneko, Hiroaki Idei
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Patent number: 8765893Abstract: Embodiments of the present disclosure encompass vinyl addition and ROMP polymers having at least one type of repeating unit that encompasses a comprise N+(CH3)3OH? moiety. Other embodiments in accordance with the disclosure include alkali anion-exchange membranes (AAEMs) made from one of such polymers, anion fuel cells (AFCs) that encompass such AAEMs and components of such AFCs, other than the AAEM, that encompass one of such polymers.Type: GrantFiled: December 13, 2010Date of Patent: July 1, 2014Assignee: Promerus, LLCInventors: Andrew Bell, Edmund Elce, Keitaro Seto
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Patent number: 8765894Abstract: Embodiments of the present disclosure encompass vinyl addition and ROMP polymers having at least one type of repeating unit that encompasses a comprise N+(CH3)3OH? moiety. Other embodiments in accordance with the disclosure include alkali anion-exchange membranes (AAEMs) made from one of such polymers, anion fuel cells (AFCs) that encompass such AAEMs and components of such AFCs, other than the AAEM, that encompass one of such polymers.Type: GrantFiled: June 10, 2011Date of Patent: July 1, 2014Assignee: Promerus, LLCInventors: Andrew Bell, Edmund Elce, Keitaro Seto
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Patent number: 8765895Abstract: The invention relates to a polymer composition that includes a branched alkene which is cationically polymerizable as well as a glass-forming comonomer and/or a vinyl comonomer containing benzocyclobutene as the pendant group. The structure of the polymer composition can take various forms: linear random copolymer, linear block copolymer, star random copolymer, star block copolymer, and other hyperbranched polymers. The copolymer composition can undergoes crosslinking at elevated temperatures (preferably above 180° C.).Type: GrantFiled: June 25, 2008Date of Patent: July 1, 2014Assignee: Innolene LLCInventors: Yonghua Zhou, Leonard Pinchuk
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Patent number: 8754179Abstract: The present discovery uses monomers which contain reversible photo-crosslinkable groups in addition to primary polymerizable groups. The mechanical properties of these materials and the reversibility of the photo-activated shape memory effect demonstrate the effectiveness of using photo-irradiation to effect change in modulus and shape memory effect. In the preferred embodiment the reaction mixture includes a photo-reactive monomer comprising a photo reactive group and a polymerizable group; a second monomer, which is more preferably a mixture of monomers, which are acrylate based; a multi-functional crosslinking agent, preferably 1,6 hexanediol diacrylate (HDODA); an initiator, preferably a free radical initiator; and a fifth, optional, component which is a modifying polymer. The mixture of the second monomer, crosslinking agent, and initiator comprise the base polymer matrix into which the photo-reactive monomer is incorporated.Type: GrantFiled: October 6, 2005Date of Patent: June 17, 2014Assignee: Cornerstone Research Group, Inc.Inventors: Tat Hung Tong, Emily Snyder
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Patent number: 8722828Abstract: A process (1) for producing a cycloolefin resin film comprising the steps of: the step (I) of mixing a cycloolefin monomer and a metathesis polymerization catalyst to prepare a polymerizable composition (A); the step (II) of coating or impregnating the supporting body with the polymerizable composition (A) at once after the step (I), and the step (III) of polymerizing the polymerizable composition (A) by polymerization; and a process (2) for producing a cycloolefin polymer sheet or film with the thickness of 1 mm or less comprising polymerizing a reactive solution containing a ruthenium complex catalyst, having a hetero atom-containing carbene compound as a ligand, and a cycloolefin monomer by ring-opening metathesis bulk polymerization, wherein the polymerization of the cycloolefin monomer is completed by heating the reactive solution to 100° C. or higher at the heating rate of 20° C./min or more.Type: GrantFiled: February 2, 2004Date of Patent: May 13, 2014Assignee: Zeon CorporationInventor: Tomoo Sugawara
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Patent number: 8685510Abstract: A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of main-chain carbon-carbon double bonds of a ring-open polymer obtained by ring-opening polymerization of 2-norbornene. The hydrogenated norbornene ring-open polymer has a weight average molecular weight determined by gel permeation chromatography (GPC) of 50,000 to 200,000, a molecular weight distribution of 1.5 to 10.0, and a melting point of 110 to 145° C. A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of carbon-carbon double bonds of a ring-open polymer obtained by ring-opening copolymerization of 2-norbornene and a substituent-containing norbornene monomer, wherein the proportion of a repeating unit (A) derived from the 2-norbornene with respect to all repeating units is 90 to 99 wt % and the proportion of a repeating unit (B) derived from the substituent-containing norbornene monomer with respect to all repeating units is 1 to 10 wt %. A resin composition and a molding material.Type: GrantFiled: December 23, 2011Date of Patent: April 1, 2014Assignee: Zeon CorporationInventors: Haruhiko Takahashi, Teiji Kohara
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Patent number: 8647730Abstract: A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of main-chain carbon-carbon double bonds of a ring-open polymer obtained by ring-opening polymerization of 2-norbornene. The hydrogenated norbornene ring-open polymer has a weight average molecular weight determined by gel permeation chromatography (GPC) of 50,000 to 200,000, a molecular weight distribution of 1.5 to 10.0, and a melting point of 110 to 145° C. A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of carbon-carbon double bonds of a ring-open polymer obtained by ring-opening copolymerization of 2-norbornene and a substituent-containing norbornene monomer, wherein the proportion of a repeating unit (A) derived from the 2-norbornene with respect to all repeating units is 90 to 99 wt % and the proportion of a repeating unit (B) derived from the substituent-containing norbornene monomer with respect to all repeating units is 1 to 10 wt %. A resin composition and a molding material.Type: GrantFiled: December 23, 2011Date of Patent: February 11, 2014Assignee: Zeon CorporationInventors: Nobuhiro Kudo, Koichi Ikeda
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Patent number: 8648160Abstract: The present invention provides an optical semiconductor sealing material comprising a radically polymerized polymer of a methacrylate ester having an alicyclic hydrocarbon group containing 7 or more carbon atoms, e.g. an adamantyl group, a norbornyl group, or a dicyclopentanyl group; and an optical semiconductor sealing material comprising a radically polymerized polymer of 50 to 97 mass % of the methacrylate ester and 3 to 50 mass % of acrylate ester having a hydroxyl group. The optical semiconductor sealing material of the present invention is highly transparent and stable to UV light and thus does not undergo yellowing. In addition, the material exhibits excellent compatibility between heat resistance and refractive index, does not undergo deformation or cracking during heating processes such as reflow soldering, and shows high processability.Type: GrantFiled: August 16, 2012Date of Patent: February 11, 2014Assignee: Idemitsu Kosan Co., Ltd.Inventors: Tomoaki Takebe, Tsuyoshi Ota, Yutaka Obata, Hiroyuki Higuchi
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Publication number: 20130331501Abstract: Embodiments of the present disclosure illustrate systems and methods for the separation of carbon nanotubes (CNTs) in solution and continuously fabrication of functionalized carbon nanotubes (CNTs). In certain embodiments, the CNTs are isolated by sonication and chemical modification of the CNTs using functionalization reactions, including thermo-initiated or sono-initiated free radical polymerization and esterification. Beneficially, sonication facilitates mechanical separation of the CNTs, while the chemical modification of the CNTs results in more favorable interactions between the CNTs and their surrounding media which enables the separated CNTs to remain isolated. Embodiments of the isolated CNTs may also be employed into coating systems.Type: ApplicationFiled: August 14, 2013Publication date: December 12, 2013Applicant: Cal Poly CorporationInventors: Phillip J. Costanzo, Keith Vorst, Greg William Curtzwiler
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Patent number: 8598288Abstract: A catalyst for a polymerization of norbornene monomers includes a transition metal complex represented by a formula (1). A method for producing a norbornene copolymer includes copolymerizing first norbornene monomers corresponding to a first monomer unit represented by a formula (2) and second norbornene monomers corresponding to a second monomer unit represented by a formula (3) in a presence of the catalyst. The transition metal complex is preferably (?-allyl) {2-[N-(2,6-diisopropylphenyl) iminomethyl]phenolate}palladium, (?-allyl) {2-[N-(2,6-diisopropylphenyl)iminomethyl]-4-fluorophenolate}palladium, (?-allyl)[2-(N-phenyliminomethyl) phenolate]palladium or (?-allyl){2-[N-(2,6-diisopropylphenyl) iminomethyl]-6-methylphenolate}palladium.Type: GrantFiled: October 30, 2012Date of Patent: December 3, 2013Assignee: Showa Denko K.K.Inventors: Satoshi Fujibe, Nobuyuki Kibino, Tsuneo Tajima
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Patent number: 8598286Abstract: The present invention is directed to a polymer comprising repeat units derived from 1,3-butadiene and a substituted butadiene of formula I or II wherein R is hydrogen, an alkyl group, aryl group, or a fused cyclic group; and wherein at least 95 percent by weight of the repeat units have a cis-1, 4 microstructure. The invention is further directed to a rubber composition and pneumatic tire comprising the polymer, and a method for making the polymer using a neodymium catalyst system.Type: GrantFiled: November 5, 2012Date of Patent: December 3, 2013Assignee: The Goodyear Tire & Rubber CompanyInventors: Margaret McGuigan Flook, Stephan Rodewald
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Patent number: 8592618Abstract: The present invention relates to a kind of novel carbene ligands and ruthenium catalysts, which is highly active and selective for ROMP and RCM reactions, respectively. It discloses the significant electronic and steric effect of different substituted carbene ligands on the catalytic activity and stability of corresponding carbene ruthenium complexes; some of novel ruthenium complexes in the invention can be broadly used as catalysts highly effectively and selective for ROMP and RCM reactions. The invention also relates to preparation of new ruthenium catalysts and the uses in metathesis. Moreover, the invention also provides effective methods of making various functional polymers by ROMP reaction in the presence of new ruthenium catalysts.Type: GrantFiled: January 8, 2010Date of Patent: November 26, 2013Assignee: Zannan Scitech Co., Ltd.Inventor: Zheng-Yun James Zhan
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Patent number: 8586160Abstract: A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of main-chain carbon-carbon double bonds of a ring-open polymer obtained by ring-opening polymerization of 2-norbornene. The hydrogenated norbornene ring-open polymer has a weight average molecular weight determined by gel permeation chromatography (GPC) of 50,000 to 200,000, a molecular weight distribution of 1.5 to 10.0, and a melting point of 110 to 145° C. A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of carbon-carbon double bonds of a ring-open polymer obtained by ring-opening copolymerization of 2-norbornene and a substituent-containing norbornene monomer, wherein the proportion of a repeating unit (A) derived from the 2-norbornene with respect to all repeating units is 90 to 99 wt % and the proportion of a repeating unit (B) derived from the substituent-containing norbornene monomer with respect to all repeating units is 1 to 10 wt %. A resin composition and a molding material.Type: GrantFiled: December 23, 2011Date of Patent: November 19, 2013Assignee: Zeon CorporationInventor: Koichi Ikeda
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Patent number: 8569427Abstract: Methods of forming polymer material from rosin-derived material are provided. For example, a plurality of functionalized resin acids having a polymerizable functional group via controlled living polymerization can be polymerized into the polymeric material such that each polymer defines a functional end group and the polymeric material has a polydispersity index of about 1 to about 1.5. The resulting polymers are also described.Type: GrantFiled: October 8, 2010Date of Patent: October 29, 2013Assignee: University of South CarolinaInventor: Chuanbing Tang
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Publication number: 20130237630Abstract: A heat-resistant cured product is efficiently produced by obtaining a semi-cured product where a curable resin composition containing a (meth)acrylate monomer, a non-conjugated vinylidene group-containing compound and a thermal radical-polymerization initiator is processed by at least one of photoirradiation and heating to give a semi-cured product having a complex viscosity of from 105 to 108 mPa·s at 25° C. and at a frequency of 10 Hz; and putting the semi-cured product in a forming die for pressure formation therein, and heating it therein for thermal polymerization to give a cured product.Type: ApplicationFiled: April 24, 2013Publication date: September 12, 2013Applicant: FUJIFILM CorporationInventors: Naoyuki MOROOKA, Rie OKUTSU, Tatsuhiko OBAYASHI, Hiroaki MOCHIZUKI
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Patent number: 8530134Abstract: Disclosed is a process for producing a photoresist polymeric compound. The process includes the steps of polymerizing a monomer mixture containing at least one monomer selected from a monomer (a) containing a group capable of leaving with an acid to allow the polymeric compound to be soluble in an alkali, a monomer (b) having a lactone skeleton, and a monomer (c) having a hydroxyl-containing alicyclic skeleton, to give a polymer; passing a solution containing the polymer through a filter including a porous membrane having an anion-exchange group to give a polymer solution; and thereafter passing the polymer solution through a filter including a porous membrane having a cation-exchange group. The polymer solution before passing through the filter including a porous membrane having a cation-exchange group preferably has a content of metals of 1000 ppb by weight or less per the weight of the polymer.Type: GrantFiled: May 18, 2010Date of Patent: September 10, 2013Assignee: Daicel Chemical Industries, Ltd.Inventor: Tadashi Teranishi
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Patent number: 8500807Abstract: The invention relates to an intraocular lens comprising at least one pharmaceutically-acceptable photochromic polymer that enables all or part of the intraocular lens to change colour reversibly when exposed to light.Type: GrantFiled: January 6, 2006Date of Patent: August 6, 2013Assignee: Carl Zeiss Meditec SASInventors: Pascal Bernard, Marc Dolatkhani, Anne Pagnoux, Christophe Hupin
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Patent number: 8487055Abstract: There is provided a polymer made from a monomer having Formula I: where: R and Y are independently selected from the group consisting of H, D, alkyl, fluoroalkyl, aryl, fluoroaryl, alkoxy, aryloxy, NR?2, R?, R? is a crosslinkable group; R? is independently selected from the group consisting of H, alkyl, fluoroalkyl, aryl, fluoroaryl, and R?; X is a leaving group; Z is C, Si, or N; Q is (ZR?n)b; a is an integer from 0 to 5; b is an integer from 0 to 20; c is an integer from 0 to 4; q is an integer from 0 to 7; and n is an integer from 1 to 2.Type: GrantFiled: December 5, 2011Date of Patent: July 16, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Nora Sabina Radu, Gene M. Rossi, Eric Maurice Smith, Yulong Shen, Weiying Gao, Reid John Chesterfield, Jeffrey A. Merlo, Daniel David Lecloux, Frederick P. Gentry
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Patent number: 8481166Abstract: A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of main-chain carbon-carbon double bonds of a ring-open polymer obtained by ring-opening polymerization of 2-norbornene. The hydrogenated norbornene ring-open polymer has a weight average molecular weight determined by gel permeation chromatography (GPC) of 50,000 to 200,000, a molecular weight distribution of 1.5 to 10.0, and a melting point of 110 to 145° C. A hydrogenated norbornene ring-open polymer obtained by hydrogenating 80% or more of carbon-carbon double bonds of a ring-open polymer obtained by ring-opening copolymerization of 2-norbornene and a substituent-containing norbornene monomer, wherein the proportion of a repeating unit (A) derived from the 2-norbornene with respect to all repeating units is 90 to 99 wt % and the proportion of a repeating unit (B) derived from the substituent-containing norbornene monomer with respect to all repeating units is 1 to 10 wt %. A resin composition and a molding material.Type: GrantFiled: December 23, 2011Date of Patent: July 9, 2013Assignee: Zeon CorporationInventors: Haruhiko Takahashi, Teiji Kohara, Nobuhiro Kudo, Koichi Ikeda, Tokudai Ogawa, Takeshi Hirata
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Patent number: 8470946Abstract: Carbon nanotube (CNT) yarns and sheets having enhanced mechanical strength using infused and bonded nano-resins. A CNT yarn or sheet is surface-activated to produce open bonds in the CNT walls prior to resin infusion. The CNT yarn or sheet is infused with a low viscosity nano-resin that penetrates spaces between individual CNTs and is cured to cross-link and chemically bond to the CNT walls, either directly or through a functional molecule, to bond the individual CNTs or ropes to each other. The nano-resin can comprise dicyclopentadiene having an uncured viscosity near that of water. The cross-linking process involves ring-opening metathesis polymerization and catalysis of the nano-resin in combination with a functionalizing material such as norbornene, to enhance bonding between the carbon and nano-resin. The process increases load capability, tensile strength, and elastic modulus of the yarns and sheets, for use as a structural component in composite materials.Type: GrantFiled: August 20, 2012Date of Patent: June 25, 2013Assignee: The Regents of the University of CaliforniaInventor: Lawrence E. Carlson
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Patent number: 8470510Abstract: A polymer for lithographic purposes has at least a repeating structural unit represented by following General Formula (I). In Formula (I), R1, R3, R4, and R6 each independently represent hydrogen atom, a halogen atom, cyano group, an alkyl group, or a haloalkyl group; R2 and R5 each independently represent hydrogen atom, cyano group, etc.; X1 and X2 each independently represent single bond, or a substituted or unsubstituted bivalent alkylene, alkenylene, or cycloalkylene group, etc.; X3 and X4 each independently represent single bond or —CO—; R7, R8, R9, and R10 each independently represent hydrogen atom, an alkyl group, or a cycloalkyl group. The polymer for lithographic purposes shows good balance between line edge roughness (LER) and etching resistance and allows very fine and uniform patterning.Type: GrantFiled: June 1, 2009Date of Patent: June 25, 2013Assignee: Daicel Chemical Industries, Ltd.Inventors: Arimichi Okumura, Keizo Inoue, Kazuki Okamoto
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Patent number: 8431325Abstract: A compound of the present invention is represented by the formula (A); wherein R1 represents a hydrogen atom or a C1 to C6 alkyl group; Z1 represents a single bond, —CO—O—* or —CO—O—(CH2)k—CO—O—*; Z2 represents a single bond, *—O—CO—, *—CO—O—, *—O—(CH2)k—CO—, *—CO—(CH2)k—O—, *—O—(CH2)k—CO—O—, *—O—CO—(CH2)k—O— or *—O—CO—(CH2)k—O—CO—; k represents an integer of 1 to 6; * represents a binding position to W; W represents a C4 to C36 (n+1) valent alicyclic hydrocarbon group or a C6 to C18 (n+1) valent aromatic hydrocarbon group, one or more hydrogen atoms contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be replaced by a halogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a C2 to C4 acyl group or —OR10; R10 represents a hydrogen atom or a group represented by the formula (R2-2); R2 represents a hydrogen atom, a group represented by the formula (R2-1) or (R2-2); n represents an integer of 1 to 3; R4, R5 and R6 independently represent a C1 to C12 hydrocarbon groupType: GrantFiled: September 1, 2010Date of Patent: April 30, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiko Hashimoto, Koji Ichikawa