Two Distinct Phenolic Reactants Or Two Or More Hydroxy Groups Or Phenate Groups Bonded To Nuclear Carbon Atoms Of The Same Benzene Ring Patents (Class 528/155)
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Patent number: 11268000Abstract: An aqueous adhesive composition comprises a thermosetting resin based on: at least one aromatic compound bearing at least two functions, one of these functions being a hydroxymethyl function and the other being an aldehyde function or a hydroxymethyl function, the aromatic compound comprising at least one aromatic ring; and at least aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functions in the meta position relative to one another, the two positions ortho to at least one of the hydroxyl functions being unsubstituted. Such an adhesive composition may especially be used to join elements made of wood; it constitutes an advantageous alternative to the use of a formaldehyde-based phenolic resin adhesive.Type: GrantFiled: April 3, 2017Date of Patent: March 8, 2022Assignee: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELINInventors: David Doisneau, Clement Michoud
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Patent number: 11091580Abstract: A rubber composition comprises at least one resin based on: (A1) at least one aromatic compound resulting from the reaction between a reactant of formula (?): where B represents CHO or CH2OH, (?) and a reactant of formula (?) or and (A2) at least one phenolic compound chosen from: (A21) at least one aromatic polyphenol comprising at least one aromatic ring bearing at least two hydroxyl functional groups in the meta position with respect to one another, the two positions ortho to at least one of the hydroxyl functional groups being unsubstituted; and/or (A22) at least one aromatic monophenol comprising at least one six-membered aromatic ring bearing a single hydroxyl functional group, the two positions ortho to the hydroxyl functional group being unsubstituted or at least one position ortho to and the position para to the hydroxyl functional group being unsubstituted.Type: GrantFiled: July 20, 2017Date of Patent: August 17, 2021Assignee: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELINInventors: David Doisneau, Odile Gavard-Lonchay, Anne-Lise Thuilliez
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Patent number: 9163106Abstract: A straight-chain unsaturated hydrocarbon group having equal to or more than 10 carbon atoms is bonded to at least one or more of meta positions of all of phenol structure units.Type: GrantFiled: May 29, 2013Date of Patent: October 20, 2015Assignee: SUMITOMO BAKELITE CO., LTD.Inventor: Yuji Suzuki
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Publication number: 20150112023Abstract: The invention relates to an in-situ process for preparing an alkylphenol-aldehyde resin. The process comprises the step of providing a raw alkylphenol composition. The raw alkylphenol composition comprises one or more alkylphenol compounds and at least about 1 wt % phenol. Each alkylphenol compound has one or more alkyl substituents. The raw alkylphenol composition is reacted directly, without pre-purification, with one or more aldehydes to form an in-situ alkylphenol-aldehyde resin. The invention also relates to an in-situ alkylphenol-aldehyde resin formed from the in-situ process, and its use in a tackifier composition and rubber composition. The tackifier composition and rubber composition containing the in-situ alkylphenol-aldehyde resin show, inter alia, improved tack performance.Type: ApplicationFiled: October 15, 2014Publication date: April 23, 2015Inventors: Timothy Edward Banach, John Morgan Whitney, Jeffrey M. Hiscock, Todd Scott Makenzie, Gennaro Barbiero
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Publication number: 20140323681Abstract: Disclosed are processes for preparing sol-gel resins from phenolic compounds and aldehydes. The process includes reacting an hydroxylated benzene and a catalyst with an aldehyde to form a liquid storage stable intermediate. The storage stable intermediate may then be stored for a period of time before being utilized in a process to prepare the sol-gel resin, in either monolith or particle form, by subsequently reacting the intermediate with an hydroxylated benzene and a catalyst.Type: ApplicationFiled: April 23, 2014Publication date: October 30, 2014Applicant: Momentive Specialty Chemicals Inc.Inventors: Stephen W. ARBUCKLE, Gabriele BADINI, John HUGGINS, Sanjay GANGAL
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Patent number: 8695752Abstract: Deep-drawn membranes formed of polyester or polycarbonate films, comprising units of Formula (I) and (II), useful for acoustic signal converters as microphones and speakers. The film can be produced by thermoplastic processes or solvent cast processes.Type: GrantFiled: January 28, 2010Date of Patent: April 15, 2014Assignee: tesa SEInventors: Kerstin Metzler, Bernhard Müssig, Frank Virus
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Patent number: 8642714Abstract: The present invention provides a phenol resin having, as a unit in its main-chain skeleton, a structure represented by the following general formula (I), as well as a resin composition using the same. According to the phenol resin of the invention, epoxylation thereof, chemical modification thereof, reaction thereof with an epoxy resin, and the like are facilitated. Phenol resins ranging from low-molecular-weight resins rich in fluidity to high-melting resins can be synthesized, and these phenol resins are industrially useful. When the phenol resin of the present invention is used as a hardening agent for epoxy resin etc., its resin composition can give a cured product of high Tg without deteriorating adhesiveness.Type: GrantFiled: January 24, 2007Date of Patent: February 4, 2014Assignee: Hitachi Chemical Company, Ltd.Inventors: Haruaki Sue, Kuniaki Satou, Osamu Matsuzaka
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Publication number: 20140017612Abstract: Polymeric materials, methods for making the polymeric materials, and photoresist formulations utilizing the polymeric materials are disclosed. In one aspect, a polymeric material is provided including a condensation product of a reaction mixture comprising an aldehyde with a phenolic monomer composition comprising m-cresol, p-cresol, 3,5-dimethyl phenol, and 2,5-dimethyl phenol. The polymeric material may be further contacted with a photoactive compound and a solvent to form a photoresist formulation.Type: ApplicationFiled: July 13, 2012Publication date: January 16, 2014Inventors: Ashok T. Reddy, Joseph E. Wentworth
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Publication number: 20130172451Abstract: A method for preparing a phenol-formaldehyde resin is provided. The method includes extracting a biomass pyrolysis oil to obtain a first phenolic mixture, and polymerizing the first phenolic mixture to form a phenol-formaldehyde resin solution under an aldehyde, an alcohol and an alkaline catalyst. The disclosure also provides a resin material prepared from the phenol-formaldehyde resin. The disclosure further provides a method for preparing a resin molding material.Type: ApplicationFiled: July 25, 2012Publication date: July 4, 2013Inventors: I-Min TSENG, Wen-Chuan HSU, Wen-Jau LEE
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Patent number: 8470930Abstract: The present invention relates to novolak resins prepared with, inter alia, one or more alkylphenols. The invention further relates to compositions comprising the novolak resins, such as vulcanizable rubber compositions, and to products obtained therewith.Type: GrantFiled: September 10, 2008Date of Patent: June 25, 2013Assignee: SI Group, Inc.Inventors: L. Scott Howard, Todd M. Aube, Timothy Edward Banach, James J. Lamb
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Patent number: 8399597Abstract: A resorcinol-modified phenolic resin composition is formed by reacting a basic catalyst, formaldehyde, water and a benzene-ol to form an intermediate composition to which resorcinol is subsequently added to reduce the presence of free formaldehyde. Optionally, an alkanolamine can be combined and reacted with the resorcinol-modified phenolic resin composition to form a resorcinol-alkanolamine-modified phenolic resin composition. The resorcinol-modified phenolic resin and the resorcinol-alkanolamine-modified phenolic resin compositions can be employed to coat abrasive products having a relatively low free formaldehyde content.Type: GrantFiled: September 19, 2008Date of Patent: March 19, 2013Assignees: Saint-Gobain Abrasives, Inc., Saint-Gobain AbrasifsInventors: Abdul Habid Pullichola, Adiseshaiah K. Seshu, Kottotil Mohan Das, Jagmohan Verma, Olivier Pons Y Moll, Philippe Espiard
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Patent number: 8349989Abstract: A method of sealing a semiconductor element which involves applying an epoxy resin composition including an epoxy resin and a phenolic resin obtained by reacting phenol, a biphenyl compound represented by the general formula (3) and benzaldehyde to a semiconductor element and curing the composition to seal the semiconductor element: wherein X in the formula (3) is a halogen, an OH group or an OCH3 group. The molar ratio of the total of the biphenyl compound and benzaldehyde relative to the phenol is from 0.27 to 0.40, and the molar ratio of benzaldehyde/biphenyl compound is from 5/95 to 40/60.Type: GrantFiled: June 2, 2011Date of Patent: January 8, 2013Assignee: Air Water Inc.Inventors: Kiyotaka Murata, Yoshihisa Sone
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Publication number: 20120041146Abstract: The present invention provides methods to functionalize and solubilize WCNT with a phenolic polymer such as a lignin or a PF resin followed by in-situ integration of this functionalized CNT in the presence of formaldehyde and phenol and/or lignin to generate either CNT-reinforced phenol-formaldehyde polymer or CNT-reinforced lignin-phenol-formaldehyde polymer in either liquid or powder form suitable as an adhesive in the manufacture of a lignocellulosic composite material such as OSB and plywood.Type: ApplicationFiled: July 27, 2011Publication date: February 16, 2012Applicants: NATIONAL RESEARCH COUNCIL OF CANADA, FPINNOVATIONSInventors: Yaolin ZHANG, Xiang-Ming WANG, Martin FENG, Gilles BRUNETTE, Fuyong CHENG, Benoit SIMARD
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Patent number: 7994271Abstract: Disclosed is a phenolic resin having flame retardance, fast curing property and low melt viscosity, which is useful for a curing agent for epoxy resin-based semiconductor sealing materials. Also disclosed are a method for producing such a phenolic resin and use of such a phenolic resin. Specifically disclosed is a phenolic resin obtained by reacting a phenol, a bismethylbiphenyl compound and an aromatic aldehyde at such a ratio that the molar ratio of the total of the bismethylbiphenyl compound and the aromatic aldehyde relative to the phenol is 0.10-0.60, and the aromatic aldehyde/the bismethylbiphenyl compound (molar ratio) is from 5/95 to 50/50. Also specifically disclosed is an epoxy resin composition composed of such a phenolic resin and an epoxy resin.Type: GrantFiled: October 16, 2006Date of Patent: August 9, 2011Assignee: Air Water Inc.Inventors: Kiyotaka Murata, Yoshihisa Sone
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Patent number: 7834124Abstract: It is an object of the invention to provide a ketone-modified resorcinol-formalin resin, which has a moderate flowability when transformed into an aqueous solution and has both a reduced content of resorcinol monomer and a reduced content of resorcinol-formalin resin of resorcinol pentanuclear or higher nuclear bodies. The invention relates to a ketone-modified resorcinol-formalin resin, which is produced by a two-step reaction and wherein a peak area corresponding resorcinol monomer is 3 to 9% and a peak area corresponding to resorcinol pentanuclear and higher nuclear bodies is 30 to 55% relative to the total peak area obtained by gel permeation chromatographic analysis of the resorcinol-formalin resin.Type: GrantFiled: January 25, 2006Date of Patent: November 16, 2010Assignee: Hodogaya Chemical Co., Ltd.Inventors: Nobuo Kaifu, Hiroshi Nakaoka, Hisatoshi Koinuma
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Patent number: 7718752Abstract: A process for producing a resorcinol-formalin resin containing no salts, having a moderate flowability when transformed into an aqueous solution, and having a reduced content of resorcinol monomer and a reduced content of resorcinol-formalin resin of resorcinol pentanuclear or higher nuclear bodies, the whole steps including an one-stage reaction and liquid-liquid distribution being conducted in the same reactor, which comprises adding resorcinol, an inorganic salt, and an organic solvent having a solubility parameter of 7.0 to 12.Type: GrantFiled: October 6, 2004Date of Patent: May 18, 2010Assignee: Hodogaya Chemical Co., Ltd.Inventors: Nobuo Kaifu, Hiroshi Nakaoka, Hisatoshi Koinuma
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Publication number: 20090326164Abstract: The invention relates to a hydroxy-aromatic resin, prepared by bringing together and reacting a hydroxy-aromatic compound and glyoxylic acid, The invention further relates to use of the resin in adhesives, laminates, and coatings.Type: ApplicationFiled: June 1, 2007Publication date: December 31, 2009Inventors: Jozef Johannes Catherina Jacobus Boonen, Wilhelmus Hubertus Joseph Boesten, Renier Henricus Maria Kierkels, Mark Martinus Maria Janssen, Rudolfus Antonius Theodorus Maria Van Benthem
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Publication number: 20090203851Abstract: The invention relates to a hydroxy-aromatic resin prepared by bringing together and letting react a hydroxy-aromatic compound of formula (I) and an alkanol hemiacetal compound of formula (II). Formula (I) is: wherein R1, R2, R3, R4 and R5 may be the same or may be different and are H, OH, a C1-C20 alkyl group, or an oligomeric or polymeric system, whereby at least one of the set consisting of R1, R3 and R5 is H. Formula (II) is: wherein R8 is a C1-C12 alkyl group, aryl group, aralkyl group or cycloalkyl group and wherein R12 is H, a C1-C12 alkyl groups aryl group, aralkyl group or cycloalkyl group. The invention further relates to use of the resin in adhesives, laminates, and coatings.Type: ApplicationFiled: June 1, 2007Publication date: August 13, 2009Applicant: DSM IP ASSETS B.V.Inventor: Rudolfus Antonius Theodorus Maria Benthem Van
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Publication number: 20090149624Abstract: A resorcinol-modified phenolic resin composition is formed by reacting a basic catalyst, formaldehyde, water and a benzene-ol to form an intermediate composition to which resorcinol is subsequently added to reduce the presence of free formaldehyde. Optionally, an alkanolamine can be combined and reacted with the resorcinol-modified phenolic resin composition to form a resorcinol-alkanolamine-modified phenolic resin composition. The resorcinol-modified phenolic resin and the resorcinol-alkanolamine-modified phenolic resin compositions can be employed to coat abrasive products having a relatively low free formaldehyde content.Type: ApplicationFiled: September 19, 2008Publication date: June 11, 2009Applicants: Saint-Gobain Abrasives, Inc., Saint-Gobain AbrasifsInventors: Abdul Habid Pullichola, Adiseshaiah K. Seshu, Kottotil Mohan Das, Jagmohan Verma, Olivier Pons Y Moll, Philippe Espiard
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Publication number: 20080293911Abstract: An anhydride and resorcinol latent catalyst system for a phenolic resole resin provides a resin having long pot life and long shelf life, yet cures quickly thereafter.Type: ApplicationFiled: May 21, 2007Publication date: November 27, 2008Applicant: Georgia-Pacific Chemicals LLCInventors: Shahid P. Qureshi, Charles C. Chan
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Patent number: 7425602Abstract: The present invention relates to novolak resins prepared with, inter alia, one or more alkylphenols. The invention further relates to compositions comprising the novolak resins, such as vulcanizable rubber compositions, and to products obtained therewith.Type: GrantFiled: November 19, 2004Date of Patent: September 16, 2008Assignee: SI Group, Inc.Inventors: L. Scott Howard, Todd M. Aube, Timothy Edward Banach, James J. Lamb
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Publication number: 20080112876Abstract: A method of stabilizing a resorcinol-aldehyde resin comprises heating a resorcinol-aldehyde resin in the substantial absence of an acid or base catalyst at a temperature from about 130° C. to about 180° C. for a sufficient amount of time to render the resin stable in an aqueous solution, wherein the resorcinol-aldehyde resin prior to heating is a novolak resin. The stabilized resins have many useful applications. For example, they can be used to make aerogels and xerogels. They also can be used to make dipping solutions to improve the adhesion between rubber and tire cords in a tire, belt, or hose.Type: ApplicationFiled: October 17, 2007Publication date: May 15, 2008Applicant: INDSPEC CHEMICAL CORPORATIONInventor: Theodore Harvey Dailey
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Patent number: 7259221Abstract: A silane-modified phenolic resin is prepared by reacting a phenolic compound (e.g., resorcinol) with an aldehyde to produce a phenolic novolak resin. The phenolic novolak resin is further reacted with at least one silane compound to produce the silane-modified phenolic resin. The reaction is typically carried out in the presence of an acid or base catalyst. The resulting resin has a lower softening point and can be used as a methylene acceptor compound in a vulcanizable rubber composition.Type: GrantFiled: March 18, 2005Date of Patent: August 21, 2007Inventors: Raj B. Durairaj, C. Michael Walkup, Mark A. Lawrence
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Patent number: 7241833Abstract: A process for production of phenolic novolak which comprises the step of conducting heterogeneous reaction of a phenol with 0.40 to 0.93 mol of an aldehyde per mol of the phenol in the presence of at least 25 parts by mass of a phosphoric acid per 100 parts by mass of the phenol. This process can give in high yield phenolic novolak with the contents of monomeric and dimeric phenols and a degree of dispersion controlled.Type: GrantFiled: November 15, 2002Date of Patent: July 10, 2007Assignee: Asahi Organic Chemicals Industry Co.., LTPInventors: Shigeki Inatomi, Noboru Tanoue
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Patent number: 7074861Abstract: A modified resorcinol resin is prepared by reacting a phenolic compound (e.g., resorcinol) with an olefinically unsaturated compound (e.g., styrene) and two types of aldehyde: a formaldehyde and an alkyl aldehyde (e.g., butyraldehyde). The reaction is typically carried out in the presence of an acid catalyst. The resulting resin has a lower softening point and can be used as a methylene acceptor compound in a vulcanizable rubber composition.Type: GrantFiled: February 18, 2003Date of Patent: July 11, 2006Assignee: INDSPEC Chemical CorporationInventors: Raj Durairaj, Mark A. Lawrence
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Patent number: 6939926Abstract: A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 ?m and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.Type: GrantFiled: February 9, 2004Date of Patent: September 6, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6875807Abstract: A silane-modified phenolic resin is prepared by reacting a phenolic compound (e.g., resorcinol) with an aldehyde to produce a phenolic novolak resin. The phenolic novolak resin is further reacted with at least one silane compound to produce the silane-modified phenolic resin. The reaction is typically carried out in the presence of an acid or base catalyst. The resulting resin has a lower softening point and can be used as a methylene acceptor compound in a vulcanizable rubber composition.Type: GrantFiled: May 28, 2003Date of Patent: April 5, 2005Assignee: Indspec Chemical CorporationInventors: Raj B. Durairaj, C. Michael Walkup, Mark A. Lawrence
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Patent number: 6734275Abstract: The present invention relates to a method of gluing wood based materials by providing an adhesive system onto wood based materials followed by curing, the adhesive system comprises a urea based amino resin and a hardener composition, wherein the hardener composition comprises an acid and a phenolic resin. The invention also relates to an adhesive system and a hardener composition as well as wood based products obtained by the method or through the use of the adhesive system.Type: GrantFiled: October 18, 2002Date of Patent: May 11, 2004Assignee: Akzo Nobel N.V.Inventors: Salme Pirhonen, Benyahia Nasli-Bakir, Ingvar Lindh
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Patent number: 6716729Abstract: There is provided a stable single-phase composition of bisphenolic stillbottoms and methods for making such compositions. There is also provided a resole and a novolac composition that includes in the manufacture of the resins the use of a stable solution of bisphenolic stillbottoms. Methods for making the resins are also provided. There is further provided a low molecular weight phenolic resin useful in the manufacture of paper laminates, such that the resin exhibits improved paper saturation and reduced phenol emissions during treating when compared to the prior art. There is also provided a laminate composition that results in a paper laminate that exhibits improved flexibility when compared to the prior art.Type: GrantFiled: March 4, 2002Date of Patent: April 6, 2004Assignee: Borden Chemical, Inc.Inventors: Stephen Wayne Arbuckle, Vinay Malhotra, John George Juras, Jr.
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Patent number: 6657016Abstract: A polyester resin composition comprising 50 equivalents/ton or more of an aromatic ring in the resin and at least one thermosetting resin selected from the group consisting of melamine resin, urea resin, benzoguanamine resin and phenol resin. The aromatic ring in the polyester resin has a phenolic hydroxyl group and at least one of ortho-position and para-position of the aromatic ring to the phenolic hydroxyl group is a hydrogen atom. The resin composition has excellent toughness at ambient temperature and heat resistance.Type: GrantFiled: March 14, 2002Date of Patent: December 2, 2003Assignee: Toyo Boseki Kabushiki KaishaInventor: Takeshi Yatsuka
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Publication number: 20030207195Abstract: Disclosed is an alkali-soluble, film-forming novolak resin mixture containing at least two novolak resins, each novolak resin containing the addition-condensation reaction product of at least one phenolic compound with at least one aldehyde source, wherein the phenolic compound for first novolak resin contains 90-100 mole % of meta-cresol, and the phenolic compound for the second novolak resin contains less than 50 mole % of meta-cresol. Also disclosed is a photosensitive composition, containing an admixture of: a) the above-mentioned novolak resin mixture; b) at least one o-quinone photoactive compound; and c) at least one photoresist solvent.Type: ApplicationFiled: April 11, 2002Publication date: November 6, 2003Inventors: J. Neville Eilbeck, Alberto D. Dioses
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Patent number: 6579963Abstract: Phenol/aldehyde resins particularly phenol/formaldehyde resins are manufactured by replacing a proportion of the phenol content by a mixture of at least two different natural materials having a phenolic content. The resulting resins which can be used in bonding composite materials are at least as effective as the resin using only phenol and more satisfactory environmentally.Type: GrantFiled: June 6, 2001Date of Patent: June 17, 2003Assignee: Enigma N.V.Inventors: Efthalia Vergopoulou-Markessini, Sophia Tsiantzi
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Patent number: 6469109Abstract: An epoxy resin composition is disclosed as containing, as essential components, an epoxy resin, an aryl ester compound obtained from a polyhydric phenol representedd by a formula (4) with a carbonyl compound represented by a general formula (2) and a cure accelerator. When cured, the resulting product has low dielectric constant and a low dielectric loss tangent. A copper-clad laminate formed using the described composition has a low dielectric constant and a low dielectric loss tangent. The copper-clad laminate exhibits excellent adhesiveness characteristics and is suitable for use in multilayer printed wiring boards in high speed operations, particularly in the high frequency region.Type: GrantFiled: June 30, 1997Date of Patent: October 22, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Youichi Ueda, Yasuhiro Endo, Mitsuhiro Shibata, Kaori Yamasaki
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Patent number: 6465599Abstract: A curing or bridging composition is useful for effecting the crosslinking of phenolic resoles and the formation of novolaks. The composition comprises from 1% to 99% by weight of partially or totally sulfonated calixarenes and from 99% to 1% of partially or totally sulfonated linear phenolic oligomers, optionally together with partially or totally sulfonated phenol. To the contrary of conventional catalysts for the crosslinking of resoles and the formation of novolaks, the composition is chemically incorporated into the molecular structure of the final products; especially the sulfonated calixarenes confer new, surprisingly improved properties to phenolic resins and novolaks and sensibly accelerate the condensation reactions.Type: GrantFiled: July 2, 1999Date of Patent: October 15, 2002Assignee: Transdiffusia S.A.Inventors: Roger Lamartine, Philippe Choquard
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Patent number: 6417317Abstract: A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho-ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.Type: GrantFiled: December 13, 1999Date of Patent: July 9, 2002Assignee: Togyo Ohka Kogyo Co., Ltd.Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
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Publication number: 20020010288Abstract: An aryl ester compound composed of a polyhydric phenol in which at least one OH group has been esterified with an organic acid or its derivatives having 1 to 20 carbon atoms, said polyhydric phenol being the condensation product of a phenolic compound represented by the general formula: 1Type: ApplicationFiled: June 30, 1997Publication date: January 24, 2002Inventors: YOUICHI UEDA, YASUHIRO ENDO, MITSUHIRO SHIBATA, KAORI YAMASAKI
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Publication number: 20010024762Abstract: A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 &mgr;m and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.Type: ApplicationFiled: February 28, 2001Publication date: September 27, 2001Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6291600Abstract: In a novel method of homo- or copolymerization of vinyl chloride, a specified coating agent is applied on the surfaces of the portions which will become into contact with the vinyl chloride monomer during the polymerization process. The coating agent is in a form of an aqueous solution of a modified condensation product of phenol and aldehyde, the pH of the solution being adjusted in a range that the product is dissolved at an ambient temperature upon coating of the solution and separates out of the solution upon being heated on the surfaces. The wall surface of the polymerization tank and the like is then coated with a thin film of the coating agent having a uniform thickness and being strongly adhered to the wall surface, thereby providing an excellent effect of preventing adhesion of the product polymer to the wall surface.Type: GrantFiled: April 9, 1993Date of Patent: September 18, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Seiichi Masuko, Ichisaburo Nakamura, Yoshimatsu Naka, Keiichi Fukuda, Akira Yamamoto, Yasuyuki Hatakeyama, Akihiro Yamaguchi, Keizaburo Yamaguchi
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Patent number: 6270899Abstract: An ester compound prepared by esterifying at least one OH group of a polyhydric phenol as a condensation product of a non-substituted or substituted resorcinol and a carbonyl compound with an organic carboxylic acid having 1 to 20 carbon atoms or a derivative thereof, which necessarily contain an organic carboxylic polyacid having 1 to 20 carbon atoms or a derivative thereof. The ester compound can be used as an epoxy resin curing agent affording a cured article having low dielectric constant, low moisture absorption and sufficient heat resistance.Type: GrantFiled: June 6, 1997Date of Patent: August 7, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhiro Endo, Toshiaki Hayashi
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Patent number: 6207789Abstract: The present invention provides a resin containing in the backbone chain a structural unit represented by the following Formula (I) or (II), as a novel phenolic resin having a high Tg, a low moisture absorption, a low molding shrinkage, high adhesive properties and high flow properties. The present invention also provides a resin composition and a molding material each containing the above resin, and an electronic component device having a device element encapsulated with it.Type: GrantFiled: February 23, 2000Date of Patent: March 27, 2001Assignee: Hitachi Chemical Co., Ltd.Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Kazuyoshi Tendo
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Patent number: 6207788Abstract: A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho—ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.Type: GrantFiled: July 24, 1998Date of Patent: March 27, 2001Assignee: Tokyo Ohka Kogya Co., Ltd.Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6165675Abstract: A water insoluble, aqueous alkali soluble novolak resin, process for producing such a novolak resin, a photoresist containing such a novolak resin, and a method for producing a semiconductor device, wherein the resin is isolated by sub surface forced steam distillation.Type: GrantFiled: April 2, 1998Date of Patent: December 26, 2000Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Daniel Aubin
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Patent number: 6159405Abstract: A fire resistant phenolic resole-resorcinol novolac system for a pultrusion process, having a much improved pot life of the two part mixture, lower emissions during processing and a much better surface finish of the pultruded composite when compared to a similar existing system. A method of making a phenolic resole for pultrusion including, but not limited to, the use of modified phenols such as p-phenyl phenol and nonyl phenol.Type: GrantFiled: April 29, 1999Date of Patent: December 12, 2000Assignee: Borden Chemical, Inc.Inventor: John G. Taylor
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Patent number: 6132549Abstract: Discloses compositions of urea dissolved in aqueous, polymerizable phenolic resole resins, wood-product laminated composite products produced with such resins, with or without the urea, and methods for the production of wood-product laminated composites with such resins. The resins contain the alkaline polymerization product of (a) formaldehyde polymerized with phenol and aliphatic hydrocarbylphenol or (b) aliphatic hydrocarbylphenol dissolved in the resin containing the polymerization product of phenol and formaldehyde, wherein the hydrocarbylphenol has from 9 to 17 carbon atoms in the hydrocarbyl group and the quantity of hydrocarbylphenol is from about 0.2% to 5% based on the weight of the aqueous resole resin. Wood-product laminate composites bound with the above resole resin, after curing, exhibit unexpectedly low water absorption, good internal bond strength and reduced thickness swell properties.Type: GrantFiled: September 22, 1998Date of Patent: October 17, 2000Assignee: Borden Chemical, Inc.Inventors: Gregory F. Nieckarz, Fred E. Carlson, William D. Detlefsen
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Patent number: 6045966Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin having consistent molecular weight and superior performance in photoresist composition, by isolating such a novolak resin fraction. A method is also provided for producing photoresist composition from such a fractionated novolak resin and for producing semiconductor devices using such a photoresist composition.Type: GrantFiled: December 15, 1997Date of Patent: April 4, 2000Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Michelle Cook, Ping-Hung Lu
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Patent number: 5985507Abstract: A high thermal alkali-soluble novolak binder resin, comprising the addition-condensation reaction product of a phenolic mixture with at least one aldehyde source, the feedstock of the phenolic mixture for the reaction comprising:(1) about 25 to about 40 weight percent of the phenolic mixture being a monomer selected from meta-cresol 2,5-xylenol or the combination thereof;(2) about 50 to about 70 weight percent of the phenolic mixture being para-cresol; and(3) about 3 to about 20 weight percent of the phenolic mixture being acetamidophenol; all percentages based on the weight of total phenol monomer feedstock.The invention is also directed to a positive working photoresist made from the composition.Type: GrantFiled: February 18, 1998Date of Patent: November 16, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
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Patent number: 5986035Abstract: Provided is a high-molecular weight high-ortho novolak type phenolic resin excellent in handleability, heat resistance characteristics, curability and electric characteristics suitable for various uses and superior in balance of properties. This high-molecular weight high-ortho novolak type phenolic resin is a condensate of a trifunctional phenol compound with an aldehyde compound, is soluble in solvents, has a weight-average molecular weight of 50,000 or more calculated by polystyrene standard, has methylene bonds at ortho-ortho position in respect to phenolic hydroxyl group in an amount of 55% or more based on total methylene bonds, and has an extraction water electric conductivity of 10 .mu.S/cm or less.Type: GrantFiled: April 9, 1998Date of Patent: November 16, 1999Assignee: Sumitomo Bakelite Company LimitedInventors: Masayuki Inagaki, Shoji Tomita
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Patent number: 5976761Abstract: A process for producing a water insoluble, aqueous alkali soluble, film forming novolak resin having low metal ions, made by the fractionation of a phenol formaldehyde condensation product, a process for producing a resin a photoresist composition of superior quality containing such novolak resin, and a method for producing a semiconductor device using such photoresist composition.Type: GrantFiled: March 25, 1998Date of Patent: November 2, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
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Patent number: 5919873Abstract: Disclosed are novel crosslinked polymers derived from methylol phenols and maleic acid species, and methods of synthesizing these macromolecules. Polyesters and chromandicarboxylic groups are the dominant linkages in the structure of general formula: ##STR1## R is H or a spacing group between aromatics, R.sub.1 is an aldehyde substituent, R.sub.2 a spacing group belonging to multihidric alcohols, a maleyl grouping, and n a whole number either 0 or 1.Type: GrantFiled: July 24, 1998Date of Patent: July 6, 1999Assignee: Rio Oeste, S.A.Inventor: Nicholas M. Irving
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Patent number: 5916933Abstract: Proppants comprising a particle coated with a composition comprising bisphenol-aldehyde novolak resin, a bisphenol homopolymer or mixtures including such polymers are disclosed. Foundry sands comprising a particle coated with a composition comprising bisphenol-aldehyde novolak resin, a bisphenol homopolymer or mixtures including such polymers are disclosed. Methods of making and using these proppant particles in subterranean formations or making and using these foundry sands in foundries are also disclosed.Type: GrantFiled: March 4, 1997Date of Patent: June 29, 1999Assignee: Borden Chemical, Inc.Inventors: Calvin K. Johnson, Kwok-tuen Tse