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)
  • Patent number: 9163106
    Abstract: 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: Grant
    Filed: May 29, 2013
    Date of Patent: October 20, 2015
    Assignee: SUMITOMO BAKELITE CO., LTD.
    Inventor: Yuji Suzuki
  • Publication number: 20150112023
    Abstract: 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: Application
    Filed: October 15, 2014
    Publication date: April 23, 2015
    Inventors: Timothy Edward Banach, John Morgan Whitney, Jeffrey M. Hiscock, Todd Scott Makenzie, Gennaro Barbiero
  • Publication number: 20140323681
    Abstract: 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: Application
    Filed: April 23, 2014
    Publication date: October 30, 2014
    Applicant: Momentive Specialty Chemicals Inc.
    Inventors: Stephen W. ARBUCKLE, Gabriele BADINI, John HUGGINS, Sanjay GANGAL
  • Patent number: 8695752
    Abstract: 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: Grant
    Filed: January 28, 2010
    Date of Patent: April 15, 2014
    Assignee: tesa SE
    Inventors: Kerstin Metzler, Bernhard Müssig, Frank Virus
  • Patent number: 8642714
    Abstract: 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: Grant
    Filed: January 24, 2007
    Date of Patent: February 4, 2014
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Kuniaki Satou, Osamu Matsuzaka
  • Publication number: 20140017612
    Abstract: 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: Application
    Filed: July 13, 2012
    Publication date: January 16, 2014
    Inventors: Ashok T. Reddy, Joseph E. Wentworth
  • Publication number: 20130172451
    Abstract: 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: Application
    Filed: July 25, 2012
    Publication date: July 4, 2013
    Inventors: I-Min TSENG, Wen-Chuan HSU, Wen-Jau LEE
  • Patent number: 8470930
    Abstract: 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: Grant
    Filed: September 10, 2008
    Date of Patent: June 25, 2013
    Assignee: SI Group, Inc.
    Inventors: L. Scott Howard, Todd M. Aube, Timothy Edward Banach, James J. Lamb
  • Patent number: 8399597
    Abstract: 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: Grant
    Filed: September 19, 2008
    Date of Patent: March 19, 2013
    Assignees: Saint-Gobain Abrasives, Inc., Saint-Gobain Abrasifs
    Inventors: Abdul Habid Pullichola, Adiseshaiah K. Seshu, Kottotil Mohan Das, Jagmohan Verma, Olivier Pons Y Moll, Philippe Espiard
  • Patent number: 8349989
    Abstract: 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: Grant
    Filed: June 2, 2011
    Date of Patent: January 8, 2013
    Assignee: Air Water Inc.
    Inventors: Kiyotaka Murata, Yoshihisa Sone
  • Publication number: 20120041146
    Abstract: 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: Application
    Filed: July 27, 2011
    Publication date: February 16, 2012
    Applicants: NATIONAL RESEARCH COUNCIL OF CANADA, FPINNOVATIONS
    Inventors: Yaolin ZHANG, Xiang-Ming WANG, Martin FENG, Gilles BRUNETTE, Fuyong CHENG, Benoit SIMARD
  • Patent number: 7994271
    Abstract: 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: Grant
    Filed: October 16, 2006
    Date of Patent: August 9, 2011
    Assignee: Air Water Inc.
    Inventors: Kiyotaka Murata, Yoshihisa Sone
  • Patent number: 7834124
    Abstract: 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: Grant
    Filed: January 25, 2006
    Date of Patent: November 16, 2010
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Nobuo Kaifu, Hiroshi Nakaoka, Hisatoshi Koinuma
  • Patent number: 7718752
    Abstract: 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: Grant
    Filed: October 6, 2004
    Date of Patent: May 18, 2010
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Nobuo Kaifu, Hiroshi Nakaoka, Hisatoshi Koinuma
  • Publication number: 20090326164
    Abstract: 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: Application
    Filed: June 1, 2007
    Publication date: December 31, 2009
    Inventors: Jozef Johannes Catherina Jacobus Boonen, Wilhelmus Hubertus Joseph Boesten, Renier Henricus Maria Kierkels, Mark Martinus Maria Janssen, Rudolfus Antonius Theodorus Maria Van Benthem
  • Publication number: 20090203851
    Abstract: 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: Application
    Filed: June 1, 2007
    Publication date: August 13, 2009
    Applicant: DSM IP ASSETS B.V.
    Inventor: Rudolfus Antonius Theodorus Maria Benthem Van
  • Publication number: 20090149624
    Abstract: 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: Application
    Filed: September 19, 2008
    Publication date: June 11, 2009
    Applicants: Saint-Gobain Abrasives, Inc., Saint-Gobain Abrasifs
    Inventors: Abdul Habid Pullichola, Adiseshaiah K. Seshu, Kottotil Mohan Das, Jagmohan Verma, Olivier Pons Y Moll, Philippe Espiard
  • Publication number: 20080293911
    Abstract: 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: Application
    Filed: May 21, 2007
    Publication date: November 27, 2008
    Applicant: Georgia-Pacific Chemicals LLC
    Inventors: Shahid P. Qureshi, Charles C. Chan
  • Patent number: 7425602
    Abstract: 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: Grant
    Filed: November 19, 2004
    Date of Patent: September 16, 2008
    Assignee: SI Group, Inc.
    Inventors: L. Scott Howard, Todd M. Aube, Timothy Edward Banach, James J. Lamb
  • Publication number: 20080112876
    Abstract: 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: Application
    Filed: October 17, 2007
    Publication date: May 15, 2008
    Applicant: INDSPEC CHEMICAL CORPORATION
    Inventor: Theodore Harvey Dailey
  • Patent number: 7259221
    Abstract: 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: Grant
    Filed: March 18, 2005
    Date of Patent: August 21, 2007
    Inventors: Raj B. Durairaj, C. Michael Walkup, Mark A. Lawrence
  • Patent number: 7241833
    Abstract: 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: Grant
    Filed: November 15, 2002
    Date of Patent: July 10, 2007
    Assignee: Asahi Organic Chemicals Industry Co.., LTP
    Inventors: Shigeki Inatomi, Noboru Tanoue
  • Patent number: 7074861
    Abstract: 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: Grant
    Filed: February 18, 2003
    Date of Patent: July 11, 2006
    Assignee: INDSPEC Chemical Corporation
    Inventors: Raj Durairaj, Mark A. Lawrence
  • Patent number: 6939926
    Abstract: 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: Grant
    Filed: February 9, 2004
    Date of Patent: September 6, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6875807
    Abstract: 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: Grant
    Filed: May 28, 2003
    Date of Patent: April 5, 2005
    Assignee: Indspec Chemical Corporation
    Inventors: Raj B. Durairaj, C. Michael Walkup, Mark A. Lawrence
  • Patent number: 6734275
    Abstract: 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: Grant
    Filed: October 18, 2002
    Date of Patent: May 11, 2004
    Assignee: Akzo Nobel N.V.
    Inventors: Salme Pirhonen, Benyahia Nasli-Bakir, Ingvar Lindh
  • Patent number: 6716729
    Abstract: 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: Grant
    Filed: March 4, 2002
    Date of Patent: April 6, 2004
    Assignee: Borden Chemical, Inc.
    Inventors: Stephen Wayne Arbuckle, Vinay Malhotra, John George Juras, Jr.
  • Patent number: 6657016
    Abstract: 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: Grant
    Filed: March 14, 2002
    Date of Patent: December 2, 2003
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventor: Takeshi Yatsuka
  • Publication number: 20030207195
    Abstract: 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: Application
    Filed: April 11, 2002
    Publication date: November 6, 2003
    Inventors: J. Neville Eilbeck, Alberto D. Dioses
  • Patent number: 6579963
    Abstract: 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: Grant
    Filed: June 6, 2001
    Date of Patent: June 17, 2003
    Assignee: Enigma N.V.
    Inventors: Efthalia Vergopoulou-Markessini, Sophia Tsiantzi
  • Patent number: 6469109
    Abstract: 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: Grant
    Filed: June 30, 1997
    Date of Patent: October 22, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Youichi Ueda, Yasuhiro Endo, Mitsuhiro Shibata, Kaori Yamasaki
  • Patent number: 6465599
    Abstract: 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: Grant
    Filed: July 2, 1999
    Date of Patent: October 15, 2002
    Assignee: Transdiffusia S.A.
    Inventors: Roger Lamartine, Philippe Choquard
  • Patent number: 6417317
    Abstract: 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: Grant
    Filed: December 13, 1999
    Date of Patent: July 9, 2002
    Assignee: Togyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20020010288
    Abstract: 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: 1
    Type: Application
    Filed: June 30, 1997
    Publication date: January 24, 2002
    Inventors: YOUICHI UEDA, YASUHIRO ENDO, MITSUHIRO SHIBATA, KAORI YAMASAKI
  • Publication number: 20010024762
    Abstract: 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: Application
    Filed: February 28, 2001
    Publication date: September 27, 2001
    Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6291600
    Abstract: 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: Grant
    Filed: April 9, 1993
    Date of Patent: September 18, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Seiichi Masuko, Ichisaburo Nakamura, Yoshimatsu Naka, Keiichi Fukuda, Akira Yamamoto, Yasuyuki Hatakeyama, Akihiro Yamaguchi, Keizaburo Yamaguchi
  • Patent number: 6270899
    Abstract: 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: Grant
    Filed: June 6, 1997
    Date of Patent: August 7, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhiro Endo, Toshiaki Hayashi
  • Patent number: 6207789
    Abstract: 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: Grant
    Filed: February 23, 2000
    Date of Patent: March 27, 2001
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Haruaki Sue, Shinsuke Hagiwara, Fumio Furusawa, Seiichi Akagi, Kazuyoshi Tendo
  • Patent number: 6207788
    Abstract: 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: Grant
    Filed: July 24, 1998
    Date of Patent: March 27, 2001
    Assignee: Tokyo Ohka Kogya Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6165675
    Abstract: 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: Grant
    Filed: April 2, 1998
    Date of Patent: December 26, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Daniel Aubin
  • Patent number: 6159405
    Abstract: 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: Grant
    Filed: April 29, 1999
    Date of Patent: December 12, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: John G. Taylor
  • Patent number: 6132549
    Abstract: 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: Grant
    Filed: September 22, 1998
    Date of Patent: October 17, 2000
    Assignee: Borden Chemical, Inc.
    Inventors: Gregory F. Nieckarz, Fred E. Carlson, William D. Detlefsen
  • Patent number: 6045966
    Abstract: 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: Grant
    Filed: December 15, 1997
    Date of Patent: April 4, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Michelle Cook, Ping-Hung Lu
  • Patent number: 5986035
    Abstract: 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: Grant
    Filed: April 9, 1998
    Date of Patent: November 16, 1999
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Masayuki Inagaki, Shoji Tomita
  • Patent number: 5985507
    Abstract: 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: Grant
    Filed: February 18, 1998
    Date of Patent: November 16, 1999
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
  • Patent number: 5976761
    Abstract: 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: Grant
    Filed: March 25, 1998
    Date of Patent: November 2, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dinesh N. Khanna, Sunit S. Dixit
  • Patent number: 5919873
    Abstract: 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: Grant
    Filed: July 24, 1998
    Date of Patent: July 6, 1999
    Assignee: Rio Oeste, S.A.
    Inventor: Nicholas M. Irving
  • Patent number: 5916933
    Abstract: 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: Grant
    Filed: March 4, 1997
    Date of Patent: June 29, 1999
    Assignee: Borden Chemical, Inc.
    Inventors: Calvin K. Johnson, Kwok-tuen Tse
  • Patent number: 5859153
    Abstract: A composition useful as a powder coating comprises an epoxy resin and a novolak compound or resin having a structure obtained from the reaction of a substituted phenol such as cresol and an aldehyde to form a substituted bis(hydroxymethyl) phenol intermediate which is then reacted with a polyhydroxyphenol containing adjacent hydroxyl groups such as catechol to yield a polyhydroxyphenol-endcapped novolak compound or resin.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: January 12, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Alan R. Kirk, Allen L. Griggs
  • Patent number: 5847058
    Abstract: A process for the production of a storage-stable, modified phenol-aldehyde resol resin includes the use of an alkylresorcinol modifier and preferably a readily-available mixture of alkylresorcinols. A binder system includes the modified phenol-aldehyde resin combined with a curing agent that includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The resin and binder system are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: December 8, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk