Material Contains A Carboxylic Acid, Anhydride Thereof, Ester Thereof, Or Salt Thereof Patents (Class 528/144)
  • Patent number: 9453098
    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: Grant
    Filed: April 23, 2014
    Date of Patent: September 27, 2016
    Assignee: HEXION INC.
    Inventors: Stephen W. Arbuckle, Gabriele Badini, John Huggins, Sanjay Gangal
  • Patent number: 9353208
    Abstract: Sol-gel resins can be prepared using one or two-step processes to produce small granules or pellets of resin that are easy to handle. The methods include agitating phenolic compounds and aldehydes in the presence of a catalyst and a solvent. The reactants are brought together over a period of time to avoid an undesirable buildup of heat within the reaction mass. Condensation of the material continues under agitation sufficient to knead the material as it gels. During this gelation, the material begins to form into smaller parts until particles, the shape of granules, are produced. The condensation continues to the degree that the material is no longer capable of sintering during packaging and storage. The material thus made can be easily discharged, packaged, portioned, and further processed.
    Type: Grant
    Filed: April 23, 2014
    Date of Patent: May 31, 2016
    Assignee: HEXION INC.
    Inventors: Stephen W. Arbuckle, Gabriele Badini, John Huggins, Sanjay Gangal
  • Publication number: 20140323680
    Abstract: Sol-gel resins can be prepared using one or two-step processes to produce small granules or pellets of resin that are easy to handle. The methods include agitating phenolic compounds and aldehydes in the presence of a catalyst and a solvent. The reactants are brought together over a period of time to avoid an undesirable buildup of heat within the reaction mass. Condensation of the material continues under agitation sufficient to knead the material as it gels. During this gelation, the material begins to form into smaller parts until particles, the shape of granules, are produced. The condensation continues to the degree that the material is no longer capable of sintering during packaging and storage. The material thus made can be easily discharged, packaged, portioned, and further processed.
    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
  • 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
  • Patent number: 8586698
    Abstract: The present invention relates to a production process for a phenols novolac resin obtained by reacting phenols with formaldehydes, wherein they are reacted in the presence of a metal compound used as a catalyst for the reaction described above, and a chelating agent is further added in order to deactivate a catalytic action of the metal compound and a resin-coated sand prepared by using the above phenols novolac resin. It is possible to provide a process for producing a phenols novolac resin having an ortho rate of 30 to 60%, suitably 40 to 55% at a good yield (70% or more) and a resin-coated sand having a high curing property prepared by using the above phenols novolac resin.
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: November 19, 2013
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Hiroyuki Kawata, Sadao Takashou, Tetsurou Saikawa
  • Patent number: 8227050
    Abstract: The present invention is directed to a UV curable coating composition, which includes one or more monomers, one or more multifunctional oligomers, one or more pigments, one or more photoinitiators, and volatile organic solvent. The coating composition can be used as a primer in repairing and refinishing automobiles. The coating composition provides short drying times and a cured coating that does not need to be wiped. A method of applying the coating composition is also provided.
    Type: Grant
    Filed: October 12, 2006
    Date of Patent: July 24, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventor: James William O'Neil
  • Publication number: 20110217554
    Abstract: A phenolic resin for shell molding is provided which generates less tar during casting and has low thermal expansion properties and high flexibility. Further, a process for producing the phenolic resin, RCS obtained by using the phenolic resin, and a shell mold obtained by using such RCS are provided. A phenolic resin having advantageous characteristics is obtained by reacting phenols and naphthols with aldehydes in the presence of at least one of divalent metal salt and oxalic acid which acts as catalyst.
    Type: Application
    Filed: May 13, 2011
    Publication date: September 8, 2011
    Applicant: Asahi Organic Chemicals Industry Co., Ltd.
    Inventors: Keiichi MORI, Tomohiro TAKAMA
  • Publication number: 20110086974
    Abstract: The present invention relates to a production process for a phenols novolac resin obtained by reacting phenols with formaldehydes, wherein they are reacted in the presence of a metal compound used as a catalyst for the reaction described above, and a chelating agent is further added in order to deactivate a catalytic action of the metal compound and a resin-coated sand prepared by using the above phenols novolac resin. It is possible to provide a process for producing a phenols novolac resin having an ortho rate of 30 to 60%, suitably 40 to 55% at a good yield (70% or more) and a resin-coated sand having a high curing property prepared by using the above phenols novolac resin.
    Type: Application
    Filed: June 3, 2009
    Publication date: April 14, 2011
    Inventors: Hiroyuki Kawata, Sadao Takeshou, Tetsurou Saikawa
  • Publication number: 20110015341
    Abstract: A phenol-formaldehyde resin, which can be obtained by alkalinically catalyzed condensation of phenol and formaldehyde in the presence of at least one salt of inorganic acids and by neutralization by means of an inorganic or organic acid following the condensation, wherein the production takes place with the addition of at least one compound of the formula R1—(CH2)n—R2, in which R1 and R2, independently of one another, stand for —C(O)R, —COOR, —CN, or —NO2, and R represents H or CH3, and n has the value of 1 or 2. Also disclosed are the production of such resins and their use as binders for mineral-fiber-based insulating products.
    Type: Application
    Filed: January 21, 2008
    Publication date: January 20, 2011
    Applicant: Dynea Oy
    Inventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
  • Patent number: 7642333
    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: Grant
    Filed: May 21, 2007
    Date of Patent: January 5, 2010
    Assignee: Georgia-Pacific Chemicals LLC
    Inventors: Shahid P. Qureshi, Charles C. Chan
  • Patent number: 7589164
    Abstract: A flexibilized resorcinolic novolak resin is prepared by reacting a phenolic compound, such as resorcinol, with an unsaturated dihydroxy, an unsaturated aldehyde, an aliphatic dialdehyde, or a mixture thereof. An aldehyde (different from the unsaturated aldehyde and the aliphatic dialdehyde) is either simultaneously or subsequently added to the reaction mixture. The flexibilized resorcinolic novolak resin can be used in an adhesive composition for enhancing the adhesion between tire cords and rubber for tire applications.
    Type: Grant
    Filed: December 6, 2006
    Date of Patent: September 15, 2009
    Inventors: Raj B. Durairaj, Mark A. Lawrence
  • 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: 7345132
    Abstract: Provided an industrially excellent method of producing a phenol novolak resin having an ortho ratio of 30% or more by: (1) a method of reacting a phenol and an aldehyde using an oxalic acid catalyst at 110 to 160° C. under pressure; or (2) a method of reacting a phenol and an aldehyde under pressure while removing the heat of reaction by a condenser with controlling a pressure so that water or an organic solvent present in the reaction system is refluxed.
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: March 18, 2008
    Assignee: Chang Chun Plastics Co. Ltd
    Inventors: Noriaki Saito, Ichishi Aizu, Nobuyuki Nakajima, Masahiro Fujiwara, Koji Yano
  • Patent number: 7321020
    Abstract: The invention relates to the polycondensation products produced by reaction of bisphenol residues from bisphenol production with an aldehyde in an acidic medium useful for the production of refractory molded bodies, of unmolded substances used in the refractory industry and, together with coating powder residues, as binding agents or binding agent components for the production of molded nonwoven fabric parts.
    Type: Grant
    Filed: July 10, 2003
    Date of Patent: January 22, 2008
    Assignee: Bakelite AG
    Inventor: Josef Suren
  • 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: 7196156
    Abstract: A flexibilized resorcinolic novolak resin is prepared by reacting a phenolic compound, such as resorcinol, with an unsaturated dihydroxy, an unsaturated aldehyde, an aliphatic dialdehyde, or a mixture thereof. An aldehyde (different from the unsaturated aldehyde and the aliphatic dialdehyde) is either simultaneously or subsequently added to the reaction mixture. The flexibilized resorcinolic novolak resin can be used in an adhesive composition for enhancing the adhesion between tire cords and rubber for tire applications.
    Type: Grant
    Filed: December 12, 2003
    Date of Patent: March 27, 2007
    Assignee: Indspec Chemical Corporation
    Inventors: Raj B. Durairaj, Mark A. Lawrence
  • 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: 6936680
    Abstract: Provided an industrially excellent method of producing a phenol novolak resin having an ortho ratio of 30% or more by: (1) a method of reacting a phenol and an aldehyde using an oxalic acid catalyst at 110 to 160° C. under pressure; or (2) a method of reacting a phenol and an aldehyde under pressure while removing the heat of reaction by a condenser with controlling a pressure so that water or an organic solvent present in the reaction system is refluxed.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: August 30, 2005
    Assignee: Chang Chun Plastics Co., Ltd.
    Inventors: Noriaki Saito, Ichishi Aizu, Nobuyuki Nakajima, Masahiro Fujiwara, Koji Yano
  • Publication number: 20040210029
    Abstract: Rosin modified phenolic resins are prepared by reacting together resin acid, fatty acid, tri- or higher-functional phenolic compound and aldehyde. The fatty acid may be Monomer (derived from the fatty acid dimerization process). The reaction mixture may optionally include &agr;,&bgr;-olefinically unsaturated carbonyl compounds and/or polyol. The resin may be dissolved in a solvent to form a varnish. The resin may be used as a component of printing inks, e.g., inks for lithographic or gravure printing.
    Type: Application
    Filed: September 3, 2003
    Publication date: October 21, 2004
    Inventor: Thomas Fontana
  • Patent number: 6774168
    Abstract: A coating composition comprising a phenolic resin, an alkoxy silane, and an acid. The coating composition of the present invention promotes adhesion between a multiple layer coating composition and a substrate and between the respective layers of the multiple layer coating composition.
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: August 10, 2004
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert E. Jennings, David N. Walters
  • Patent number: 6730769
    Abstract: (i) As a primary reaction, m-cresol is allowed to react with propionaldehyde in the presence of an acid catalyst and thereby yields a polymer having a weight average molecular weight Mw of 200 to 500 and a molecular weight distribution Mw/Mn of 1.7 or less, and (ii) as a secondary reaction, the polymer is allowed to react with 3,4-xylenol and formaldehyde and thereby yields a novolak resin having an Mw of 1000 to 20000. By adding a specific photosensitizer, the novolak resin yields a positive photoresist composition.
    Type: Grant
    Filed: May 1, 2002
    Date of Patent: May 4, 2004
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akira Katano, Mitsuo Hagihara, Ken Miyagi, Toshiaki Tachi
  • Patent number: 6713591
    Abstract: This invention relates to an aromatic oligomer represented by the following formula (1): (A—F)n—A   (1) wherein A is a unit comprising (a) 30-90 wt % of a bicyclic or tricyclic aromatic compound and (b) 10-70 wt % of a phenol, F is methylene or a mixture of methylene and —CH2OCH2— and n is a number of 1-100. The aromatic oligomer is obtained by and reaction of a polycyclic aromatic compound such as naphthalene and benzothiophene, a phenol and formaldehyde compound in the presence of an acid catalyst. The aromatic oligomer is odorless and useful for various applications. In particular, when incorporated in rubber or resin, the aromatic oligomer can perform execellently as a tackifier in a wide temperature range or perform excellently as a vibration damping agent.
    Type: Grant
    Filed: March 5, 2002
    Date of Patent: March 30, 2004
    Assignee: Nippon Steel Chemicals Co., Ltd.
    Inventors: Toshihide Senzaki, Takahiro Imamura
  • Patent number: 6646095
    Abstract: A process for the manufacture of copolymers of formaldehyde and diphenyl oxide and a carboxylic acid uses and acid with a pKa in the range of 1.2 to 3 as the catalyst.
    Type: Grant
    Filed: January 16, 2002
    Date of Patent: November 11, 2003
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Kelly J. Seheult, Shane M. Carter, Lawrence J. Scotchie
  • Patent number: 6642345
    Abstract: Preparation process for a novolak aralkyl resin having excellent heat resistance and curing property by reacting 0.4 to 0.8 mol of an aralkyl compound based on one mol of the low molecular weight novolak containing 90% by weight or more of bi-nuclear novolak in the presence of an acidic catalyst, the process comprising at first melting the low molecular weight novolak, heating it up to a reaction temperature, then adding 0.001 to 0.05% by weight of the acidic catalyst to the total amount of the low molecular weight novolak and the aralkyl compound, then continuously adding the aralkyl compound for reaction, neutralizing the residual acidic catalyst after the completion of the reaction, a novolak aralkyl resin obtained by the preparation process and a novolak aralkyl resin composition containing said resin.
    Type: Grant
    Filed: January 2, 2002
    Date of Patent: November 4, 2003
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Teruo Yuasa, Hiroaki Narisawa, Masahiro Kaneko
  • Patent number: 6608161
    Abstract: The present invention provides a process for producing phenol-dicarbonyl condensates high in fluorescence by reacting a phenolic compound with a 1,2-dicarbonyl compound in the presence of a catalyst selected from one or more carboxylic acid(s) or one or more carboxylic acid precursor(s). The present invention further provides phenol-dicarbonyl condensates, epoxy resins, epoxy resin systems and laminates prepared using these phenol-dicarbonyl condensates.
    Type: Grant
    Filed: March 3, 2000
    Date of Patent: August 19, 2003
    Assignee: Resolution Performance Products LLC
    Inventors: Larry Steven Corley, Anthony Michael Pigneri
  • Publication number: 20020128423
    Abstract: Preparation process for a novolak aralkyl resin having excellent heat resistance and curing property by reacting 0.4 to 0.8 mol of an aralkyl compound based on one mol of the low molecular weight novolak containing 90% by weight or more of bi-nuclear novolak in the presence of an acidic catalyst, the process comprising at first melting the low molecular weight novolak, heating it up to a reaction temperature, then adding 0.001 to 0.05% by weight of the acidic catalyst to the total amount of the low molecular weight novolak and the aralkyl compound, then continuously adding the aralkyl compound for reaction, neutralizing the residual acidic catalyst after the completion of the reaction, a novolak aralkyl resin obtained by the preparation process and a novolak aralkyl resin composition containing said resin.
    Type: Application
    Filed: January 2, 2002
    Publication date: September 12, 2002
    Inventors: Teruo Yuasa, Hiroaki Narisawa, Masahiro Kaneko
  • 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: 6214964
    Abstract: A process for forming a phenol formaldehyde resin, the process comprising the steps of: (i) reacting phenol with an excess of a formaldehyde material in the presence of an acid or base catalyst until water separates from the reactants as an immiscible layer; (ii) adding a mixture comprising an excess of polyhydric alcohol and an aromatic dicarboxylic or tricarboxylic acid, salt or anhydride thereof to the phenol and formaldehyde reaction mixture followed by addition of an alpha hydroxy acid; (iii) adding a non-aqueous solvent, wherein at least some of said water is removed either before addition of the mixture preparated in step (ii) or after addition of the alpha hydroxy acid; (iv) preparing a solution comprising a Lewis acid, a polyhydric alcohol, an alpha hydroxy acid, a non-aqueous solvent, an aromatic sulphonic acid and sulphuric or hydrochloric acid; (v) adding the solution formed in step (iv) to the mixture formed in step (ii) and allowing the mixture to cure.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: April 10, 2001
    Inventor: Barry William Ryan
  • Patent number: 6150492
    Abstract: A two-part adhesive is provided wherein the first part comprises a stable aqueous alkaline monohydroxylic phenolic resole resin solution containing a methylene donor such as oxazolidine or a methylolurea and the second part comprises a stable resorcinolic resin precondensate having a shortage of formaldehyde and optionally containing a catalyst such as an ester functional compound for the resole resin. The resin in each part exhibits viscosity stability of an unmodified resin until mixed with the other part wherein the methylene donor, of the first part catalyzes the resorcinolic resin of the second part and the catalyst, when used, of the second part catalyzes the monohydroxylic phenolic resole resin of the first part. The adhesive finds utility in the production of structural lignocellulosic panels.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: November 21, 2000
    Assignee: Borden Chemical, Inc.
    Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
  • Patent number: 6121412
    Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin, by:a) condensing formaldehyde with one or more phenolic compounds, and thereby producing a novolak resin;b) adding a photoresist solvent, and optionally a water-soluble organic polar solvent;c) feeding the mixture into a liquid/liquid centrifuge and feeding a C.sub.5 -C.sub.8 alkane, water or aromatic hydrocarbon solvent into the liquid/liquid centrifuge at a ratio of optional water-soluble organic polar solvent and photoresist solvent to C.sub.5 -C.sub.8 alkane, water or aromatic solvent, of from 5:1 to 0.5:1;d) rotating the liquid/liquid centrifuge containing the mixture at a speed of at least 500 rpm and thereby separating the mixture into two phases, collecting the two phases;e) optionally separating the lighter phase (L) into two second phases;f) removing residual C.sub.5 -C.sub.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: September 19, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, M. Dalil Rahman, John J. Kokoszka, Balaji Narasimhan
  • Patent number: 6100364
    Abstract: A water-reducible binder for coatings comprises the reaction products of a) a phenolic resin comprising the reaction product of bisphenol A, t-butyl phenol and formaldehyde; b) an alkylene carbonate alkoxylating agent; c) a diol selected form the group consisting of 1,4-cyclohexanedimethanol, 3,5,5-trimethylpentane diol and neopentyl glycol; and d) trimellitic anhydride. Methods for preparing such a water-reducible binder and coating systems comprising such a binder are also disclosed.
    Type: Grant
    Filed: May 4, 1999
    Date of Patent: August 8, 2000
    Assignee: U.S. Polymers, Inc.
    Inventors: Robert J. Gaal, Jr., Roger W. Heitland
  • Patent number: 6090533
    Abstract: The present invention provides a method for producing a water insoluble, aqueous alkali soluble novolak resins having consistent molecular weight and superior performance in photoresist composition, by isolating such novolak resin without high temperature distillation. A method is also provided for producing photoresist composition from such a novolak resin and for producing semiconductor devices using such a photoresist composition.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: July 18, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Ping-Hung Lu
  • Patent number: 6046252
    Abstract: A binder composition of a phenolic novolac resin and a (lower) alkoxylated triazine-formaldehyde resin curing agent is disclosed. The triazine resins have sufficient carbon atoms in the alkoxy groups so as to provide a curing agent having a water solubility of less than 15%. The binder cures at high temperatures so as to provide improved flow and prolonged workability to the composition. The compositions are useful in refractory applications having a need for high temperature curing agents such as for maintenance and repair within refractory vessels by gunning/spraying, manufacture of electrodes by the Soderberg method, and for use in blast furnace tap holes.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: April 4, 2000
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur H. Gerber
  • 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: 5939511
    Abstract: The invention is directed to purification of phenolic resins and to a process for preparing an organic photoresist coating composition. The process comprises reacting one or more phenols to form a crude phenolic resin. The crude phenolic resin formed is then separated from its reaction mixture and dissolved in an aqueous insoluble organic solvent in an organic solvent that is a solvent for the photoresist coating composition. The solution so formed is then mixed with an aqueous phase to extract water soluble impurities from the resin solution into the aqueous phase. Finally, the purified resin solution is further diluted with additional photoresist solvent.
    Type: Grant
    Filed: April 8, 1998
    Date of Patent: August 17, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Suzanne M. Coley
  • Patent number: 5928836
    Abstract: The present invention provides a method for producing a film forming, fractionated novolak resin copolymer exhibiting fast photospeed and superior performance in a photoresist composition. A method is also provided for producing photoresist composition from such a fractionated novolak resin copolymer and for producing semiconductor devices using such a photoresist composition.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: July 27, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Stanley F. Wanat, Michelle M. Cook, Douglas S. McKenzie, Sunit S. Dixit
  • Patent number: 5910559
    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 novolak resin fractions without high temperature distillation. 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 18, 1996
    Date of Patent: June 8, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Ping-Hung Lu, Michelle Cook
  • 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: 5719228
    Abstract: The present invention relates to a glass fiber binding composition having an effective binding amount of an aqueous compatible furan resin mixed with sufficient water to result in a binding composition having from 0.5 to 80% nonvolatile. The aqueous compatible furan resin is the reaction product of a source of ammonia and a first reaction product, the first reaction product being derived from the reaction of an acidic furan resin, a source of reactable formaldehyde, and a formaldehyde scavenger. The invention further pertains to a process of binding glass fibers at junctions of the fibers comprising the steps of providing glass fibers, applying an effect binding amount of the binding composition of the invention to the glass fibers such that the binder is present at a portion of the junctions, and curing the resin at the junctions of the glass fibers.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: February 17, 1998
    Assignees: Schuller International, Inc., QO Chemicals Inc.
    Inventors: Thomas John Taylor, William Henry Kielmeyer, Carl A. Rude
  • Patent number: 5686506
    Abstract: A binder solution of a phenolic novolak resin in solvent, preferably furfuryl alcohol containing at least one chemical agent such as amines containing one to five, preferably two to four, nitrogen atoms, glycerine or mixtures thereof. Preferably, the binder solution contains about 0.2 to about 1.5 weight percent water. The binder solution is for binding refractory objects, preferably those containing doloma (calcined dolomite) aggregate. Methods of mixing these ingredients and using the mixture are also disclosed. Bricks made from the doloma aggregate mixed with the binder solution show good ambient temperature green strength and enhanced modulus of rupture after curing and coking.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: November 11, 1997
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur Harry Gerber
  • Patent number: 5663246
    Abstract: Cyclic acetal derivative of a resole includes the reaction product of an ortho resole compound with a carbonyl compound or a carbonyl compound derivative. The cyclic acetal derivatives of phenolic resole compounds exhibit enhanced storage stability and can be readily activated at elevated temperatures to prepare phenolic based adhesives and coatings.
    Type: Grant
    Filed: October 26, 1994
    Date of Patent: September 2, 1997
    Assignee: Lord Corporation
    Inventors: Esther Spaltenstein, Ernest B. Troughton, Jr.
  • Patent number: 5591810
    Abstract: Curable furan resins modified with phenolic resins for use as binders for cements and coating compositions having improved thermal stability, processes for their preparation and their use.Preparation of curable furan resins modified with phenolic resins based on condensation products of alkylidenepolyphenols of the novolak type with furfuryl alcohol or mixtures thereof with other reactive furan derivatives, furthermore curable solutions thereof in reactive organic solvents, processes for their preparation and their use as binders having improved thermal stability for preparing self-curing, chemically resistant and high-temperature-resistant cements and coating compositions.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: January 7, 1997
    Assignee: Hoechst Aktiengesselschaft
    Inventors: Wolfgang Hesse, Klaus Rauhut
  • Patent number: 5580949
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions, utilizing treated ion exchange resins. A method is also provided for producing photoresist composition having a very low level of metal ions from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: December 3, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Dana L. Durham
  • Patent number: 5571886
    Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: November 5, 1996
    Assignee: Shipley Company, Inc.
    Inventor: Anthony Zampini
  • Patent number: 5567743
    Abstract: This invention relates to a process for reclaiming ester-cured phenolic resin bonded sand. The process comprises contacting attrition reclaimed sand with a compound which converts potassium compounds to a form having a melting point of least 550.degree. C., and then thermally treating the sand at a temperature below that which the resulting potassium compound fuses.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: October 22, 1996
    Assignee: Asland Inc.
    Inventors: Andrew D. Busby, Philip Vernon
  • Patent number: 5567797
    Abstract: The object of the present invention is a polyamide composition containing, in reference to the polyamide composition 0.1 to 1 wt. % terephthaldialdehyde and/or its acetals of C.sub.1 --C.sub.4 alcohols and optionally 3 to 30 wt. % melamine and/or melamine cyanurate as well as a process for the production of the polyamide, a process to increase the shock resistance, notched impact resistance and viscosity of flameproof, halogen-free polyamides, and a process to increase the mass of such polyamides.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: October 22, 1996
    Assignee: A. Schulman, Inc.
    Inventors: Hubert Christ, Wolfgang Schneider
  • Patent number: 5534612
    Abstract: The present invention relates to a glass fiber binding composition having an effective binding amount of an aqueous compatible furan resin mixed with sufficient water to result in a binding composition having from 0.5 to 80% nonvolatile. The aqueous compatible furan resin is the reaction product of a source of ammonia and a first reaction product, the first reaction product being derived from the reaction of an acidic furan resin, a source of reactable formaldehyde, and a formaldehyde scavenger. The invention further pertains to a process of binding glass fibers at junctions of the fibers comprising the steps of providing glass fibers, applying an effect binding amount of the binding composition of the invention to the glass fibers such that the binder is present at a portion of the junctions, and curing the resin at the junctions of the glass fibers.
    Type: Grant
    Filed: May 19, 1993
    Date of Patent: July 9, 1996
    Assignee: Schuller International, Inc.
    Inventors: Thomas J. Taylor, William H. Kielmeyer
  • Patent number: 5470924
    Abstract: A process for forming a phenol formaldehyde resin including the steps of: (i) forming a first additive including a glycol and an aromatic dicaborxylic acid; (ii) adding said first additive as well as an alpha hydroxy acid to a first resin component comprising resin precursors including phenol, formaldehyde, an acid catalyst or a base catalyst after said precursors have reacted for 40-55 minutes and/or when water has separated from said precursors; (iii) isolating or storing said first resin component which is maintained in a non cured state by the addition of said first additive; (iv) forming a second additive including zinc chloride, an alpha hydroxy acid, para toluene sulphonic acid, sulphuric or hydrochloric acid and a non aqueous solvent; (v) adding said second additive to a second resin component which includes resin precursors phenol, formaldehyde, methanol and an aliphatic dicarboxylic acid after said precursors have reacted for 20-30 minutes; (vi) combining said first resin component and said second r
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: November 28, 1995
    Inventor: Barry W. Ryan
  • Patent number: 5395915
    Abstract: Herein disclosed is a method for simultaneously preparing a highly pure bisphenol F and/or a bisphenol F for general use and a novolak phenol resin and/or a high molecular weight novolak phenol resin comprising the steps of:(1) a preparation step comprising reacting phenol with formaldehyde in the presence of an acid catalyst and removing the acid catalyst, water and the unreacted phenol from the resulting reaction product to give a crude bisphenol F;(2) a distillation step comprising distilling a part of the crude bisphenol F to give a highly pure bisphenol F, as a distillate, having a binuclear moiety-content of not less than 95% by weight and a novolak phenol resin, as a still-bottom product, having a binuclear moiety-content of not more than 15% by area;(3) a step for mixing the highly pure bisphenol F with the remaining crude bisphenol F to give a bisphenol F for general use; and(4) a step for polymerizing the novolak phenol resin with formaldehyde in the presence of an acid catalyst to give a high molec
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Satoru Ito, Tomoko Takashima, Takashi Kitamura
  • Patent number: 5359024
    Abstract: The invention relates to a process for the preparation of a phenol-formaldehyde resin by causing phenol and formaldehyde to condense under the influence of a basic catalyst, the catalyst being an aqueous solution containing alkali metal ions, carbonate ions, ions of carboxylic acids and one or more ions chosen from the group comprising transition metal ions and borates.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: October 25, 1994
    Assignee: DSM N.V.
    Inventors: Renier H. M. Kierkels, van Kempen Carolien H. M., Henricus A. C. Baur