Material Contains A Carboxylic Acid, Anhydride Thereof, Ester Thereof, Or Salt Thereof Patents (Class 528/144)
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Patent number: 9453098Abstract: 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: GrantFiled: April 23, 2014Date of Patent: September 27, 2016Assignee: HEXION INC.Inventors: Stephen W. Arbuckle, Gabriele Badini, John Huggins, Sanjay Gangal
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Patent number: 9353208Abstract: 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: GrantFiled: April 23, 2014Date of Patent: May 31, 2016Assignee: HEXION INC.Inventors: Stephen W. Arbuckle, Gabriele Badini, John Huggins, Sanjay Gangal
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Publication number: 20140323680Abstract: 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: 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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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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Patent number: 8586698Abstract: 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: GrantFiled: June 3, 2009Date of Patent: November 19, 2013Assignee: Hitachi Chemical Company, Ltd.Inventors: Hiroyuki Kawata, Sadao Takashou, Tetsurou Saikawa
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Patent number: 8227050Abstract: 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: GrantFiled: October 12, 2006Date of Patent: July 24, 2012Assignee: E I du Pont de Nemours and CompanyInventor: James William O'Neil
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Publication number: 20110217554Abstract: 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: ApplicationFiled: May 13, 2011Publication date: September 8, 2011Applicant: Asahi Organic Chemicals Industry Co., Ltd.Inventors: Keiichi MORI, Tomohiro TAKAMA
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Publication number: 20110086974Abstract: 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: ApplicationFiled: June 3, 2009Publication date: April 14, 2011Inventors: Hiroyuki Kawata, Sadao Takeshou, Tetsurou Saikawa
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Publication number: 20110015341Abstract: 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: ApplicationFiled: January 21, 2008Publication date: January 20, 2011Applicant: Dynea OyInventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
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Patent number: 7642333Abstract: 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: GrantFiled: May 21, 2007Date of Patent: January 5, 2010Assignee: Georgia-Pacific Chemicals LLCInventors: Shahid P. Qureshi, Charles C. Chan
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Patent number: 7589164Abstract: 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: GrantFiled: December 6, 2006Date of Patent: September 15, 2009Inventors: Raj B. Durairaj, Mark A. Lawrence
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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: 7345132Abstract: 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: GrantFiled: January 19, 2005Date of Patent: March 18, 2008Assignee: Chang Chun Plastics Co. LtdInventors: Noriaki Saito, Ichishi Aizu, Nobuyuki Nakajima, Masahiro Fujiwara, Koji Yano
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Patent number: 7321020Abstract: 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: GrantFiled: July 10, 2003Date of Patent: January 22, 2008Assignee: Bakelite AGInventor: Josef Suren
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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: 7196156Abstract: 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: GrantFiled: December 12, 2003Date of Patent: March 27, 2007Assignee: Indspec Chemical CorporationInventors: Raj B. Durairaj, Mark A. Lawrence
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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: 6936680Abstract: 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: GrantFiled: December 4, 2001Date of Patent: August 30, 2005Assignee: Chang Chun Plastics Co., Ltd.Inventors: Noriaki Saito, Ichishi Aizu, Nobuyuki Nakajima, Masahiro Fujiwara, Koji Yano
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Publication number: 20040210029Abstract: 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: ApplicationFiled: September 3, 2003Publication date: October 21, 2004Inventor: Thomas Fontana
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Patent number: 6774168Abstract: 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: GrantFiled: November 21, 2001Date of Patent: August 10, 2004Assignee: PPG Industries Ohio, Inc.Inventors: Robert E. Jennings, David N. Walters
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Patent number: 6730769Abstract: (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: GrantFiled: May 1, 2002Date of Patent: May 4, 2004Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akira Katano, Mitsuo Hagihara, Ken Miyagi, Toshiaki Tachi
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Patent number: 6713591Abstract: 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: GrantFiled: March 5, 2002Date of Patent: March 30, 2004Assignee: Nippon Steel Chemicals Co., Ltd.Inventors: Toshihide Senzaki, Takahiro Imamura
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Patent number: 6646095Abstract: 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: GrantFiled: January 16, 2002Date of Patent: November 11, 2003Assignee: National Starch and Chemical Investment Holding CorporationInventors: Kelly J. Seheult, Shane M. Carter, Lawrence J. Scotchie
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Patent number: 6642345Abstract: 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: GrantFiled: January 2, 2002Date of Patent: November 4, 2003Assignee: Mitsui Chemicals, Inc.Inventors: Teruo Yuasa, Hiroaki Narisawa, Masahiro Kaneko
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Patent number: 6608161Abstract: 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: GrantFiled: March 3, 2000Date of Patent: August 19, 2003Assignee: Resolution Performance Products LLCInventors: Larry Steven Corley, Anthony Michael Pigneri
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Publication number: 20020128423Abstract: 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: ApplicationFiled: January 2, 2002Publication date: September 12, 2002Inventors: Teruo Yuasa, Hiroaki Narisawa, Masahiro Kaneko
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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: 6214964Abstract: 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: GrantFiled: February 18, 2000Date of Patent: April 10, 2001Inventor: Barry William Ryan
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Patent number: 6150492Abstract: 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: GrantFiled: February 4, 1994Date of Patent: November 21, 2000Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
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Patent number: 6121412Abstract: 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: GrantFiled: October 14, 1999Date of Patent: September 19, 2000Assignee: Clariant Finance (BVI) LimitedInventors: Stanley F. Wanat, M. Dalil Rahman, John J. Kokoszka, Balaji Narasimhan
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Patent number: 6100364Abstract: 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: GrantFiled: May 4, 1999Date of Patent: August 8, 2000Assignee: U.S. Polymers, Inc.Inventors: Robert J. Gaal, Jr., Roger W. Heitland
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Patent number: 6090533Abstract: 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: GrantFiled: November 6, 1998Date of Patent: July 18, 2000Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Ping-Hung Lu
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Patent number: 6046252Abstract: 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: GrantFiled: February 25, 1997Date of Patent: April 4, 2000Assignee: Borden Chemical, Inc.Inventor: Arthur H. Gerber
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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: 5939511Abstract: 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: GrantFiled: April 8, 1998Date of Patent: August 17, 1999Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Suzanne M. Coley
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Patent number: 5928836Abstract: 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: GrantFiled: September 29, 1997Date of Patent: July 27, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Stanley F. Wanat, Michelle M. Cook, Douglas S. McKenzie, Sunit S. Dixit
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Patent number: 5910559Abstract: 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: GrantFiled: December 18, 1996Date of Patent: June 8, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Ping-Hung Lu, Michelle Cook
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Patent number: 5859153Abstract: 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: GrantFiled: June 21, 1996Date of Patent: January 12, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Kirk, Allen L. Griggs
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Patent number: 5719228Abstract: 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: GrantFiled: January 6, 1995Date of Patent: February 17, 1998Assignees: Schuller International, Inc., QO Chemicals Inc.Inventors: Thomas John Taylor, William Henry Kielmeyer, Carl A. Rude
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Patent number: 5686506Abstract: 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: GrantFiled: April 4, 1995Date of Patent: November 11, 1997Assignee: Borden Chemical, Inc.Inventor: Arthur Harry Gerber
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Patent number: 5663246Abstract: 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: GrantFiled: October 26, 1994Date of Patent: September 2, 1997Assignee: Lord CorporationInventors: Esther Spaltenstein, Ernest B. Troughton, Jr.
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Patent number: 5591810Abstract: 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: GrantFiled: April 11, 1995Date of Patent: January 7, 1997Assignee: Hoechst AktiengesselschaftInventors: Wolfgang Hesse, Klaus Rauhut
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Patent number: 5580949Abstract: 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: GrantFiled: June 2, 1995Date of Patent: December 3, 1996Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5571886Abstract: 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: GrantFiled: March 21, 1994Date of Patent: November 5, 1996Assignee: Shipley Company, Inc.Inventor: Anthony Zampini
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Patent number: 5567743Abstract: 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: GrantFiled: May 12, 1995Date of Patent: October 22, 1996Assignee: Asland Inc.Inventors: Andrew D. Busby, Philip Vernon
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Patent number: 5567797Abstract: 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: GrantFiled: February 27, 1995Date of Patent: October 22, 1996Assignee: A. Schulman, Inc.Inventors: Hubert Christ, Wolfgang Schneider
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Patent number: 5534612Abstract: 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: GrantFiled: May 19, 1993Date of Patent: July 9, 1996Assignee: Schuller International, Inc.Inventors: Thomas J. Taylor, William H. Kielmeyer
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Patent number: 5470924Abstract: 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 rType: GrantFiled: November 24, 1993Date of Patent: November 28, 1995Inventor: Barry W. Ryan
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Patent number: 5395915Abstract: 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 molecType: GrantFiled: August 12, 1993Date of Patent: March 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shigeru Iimuro, Satoru Ito, Tomoko Takashima, Takashi Kitamura
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Patent number: 5359024Abstract: 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: GrantFiled: August 17, 1993Date of Patent: October 25, 1994Assignee: DSM N.V.Inventors: Renier H. M. Kierkels, van Kempen Carolien H. M., Henricus A. C. Baur