Material Contains An Alcohol, Inorganic Alcoholate, Or Ether Patents (Class 528/142)
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Patent number: 9951256Abstract: Epoxy adhesive compositions contain a heat-activatable catalyst. The heat-activatable catalyst includes a tertiary amine catalyst and a novolac resin that has a weight average molecular weight of at least 3000. One-component epoxy adhesive formulations that contain the heat-activatable catalyst have unexpectedly good storage stability.Type: GrantFiled: March 3, 2015Date of Patent: April 24, 2018Assignee: Dow Global Technologies LLCInventors: Ming Ming, Shaoguang Feng, Yan Fei Liu, Robert D J Froese, Andreas Lutz, Glenn G. Eagle, Gary L. Jialanella, Eric E. Cole, Michael R. Golden
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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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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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Patent number: 7834126Abstract: The invention relates to amide-containing polymers of the general formula (I) A-X—CO—(CH2)2—NR1—R2—[Y—R3—Y—R4)a—B??(I) and also their salts with carboxylic acids, phosphoric esters and sulphonic acids. The invention further relates to processes for preparing the amide-containing polymers and to their use as rheology control agents.Type: GrantFiled: October 10, 2006Date of Patent: November 16, 2010Assignee: BYK-Chemie GmbHInventors: Karlheinz Haubennestel, Stefan Moessmer, Ulrich Orth, Daniela Betcke
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Patent number: 7683155Abstract: A phenolic novolak having the contents of a monomeric phenol and a dimeric phenol and a degree of dispersion controlled can be obtained in high yield by a process for production of a phenolic novolak having a step of conducting a heterogeneous reaction of a phenol and an aldehyde in the presence of a phosphoric acid and an unreactive oxygen-containing organic solvent as a reaction cosolvent.Type: GrantFiled: August 29, 2003Date of Patent: March 23, 2010Assignee: Asahi Organic Chemicals Industry Col., Ltd.Inventors: Shigeki Inatomi, Noboru Tanoue, Motoji Yokoyama, Hirofumi Shinohara, Satoshi Takehara
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Patent number: 7669720Abstract: Membranes comprising functional polyarylether having structural units of formula I are useful for hemodialysis and hemofiltration: wherein X is selected from Br, NR4R5, OOCR6, OR7, NR4CONR5R6, NR4COOR5R6 and combinations thereof; R1, R2 and R3 are independently at each occurrence CH2X, H, halo, cyano, nitro, a C1-C12aliphatic radical, a C3-C12cycloaliphatic radical, a C3-C12aromatic radical or a combination thereof; R4 and R5 are independently H, a C1-10 aliphatic radical, a C3-C12cycloaliphatic radical, a C3-C12 aromatic radical, or a combination thereof; R6 is H, a C2-10 aliphatic radical, a C3-C12 cycloaliphatic radical, a C3-C12 aromatic radical or a combination thereof; R7 is OCH2CH2(OCH2CH2)nOH or OOCCH2(OCH2CH2)nCH3; Z is a direct bond, O, S, SO, SO2, CO, phenylphospinyl oxide, alkenyl, alkynyl, a C1-C12aliphatic radical, a C3-C12cycloaliphatic radical, a C3-C12 aromatic radical or a combination thereof; a, b, and c are independently 1 or 2; and m, n and p are independently 0 or 1.Type: GrantFiled: December 15, 2006Date of Patent: March 2, 2010Assignee: General Electric CompanyInventors: Yanshi Zhang, Daniel Steiger, Joseph Anthony Suriano, Gary William Yeager
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Patent number: 7662902Abstract: A phenolic resin having not more than 5 wt% of free bisphenol and a molecular weight distribution Mw/Mn of not more than 2.0 is prepared by reacting a bisphenol and aldehyde in the presence of an alkaline catalyst at a temperature of from 0° C. to 100° C., neutralizing with an acid, adding an acid to adjust the pH to from 0 to 6, heating to a temperature of from 50° C. to 200° C, and vacuuming to recover the phenolic resin.Type: GrantFiled: November 9, 2006Date of Patent: February 16, 2010Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen Yuan Hwang, An Pang Tu, Chun Hsiung Kao, Fang Shian Su
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Patent number: 6984710Abstract: An alkoxylated alkylphenol-formaldehyde-diamine polymer prepared by alkoxylating an alkylphenol-formaldehyde-diamine polymer and use of the alkoxylated alkylphenol-formaldehyde-diamine polymer to resolve water-in-oil emulsions, especially emulsions of water in crude oil.Type: GrantFiled: October 13, 2003Date of Patent: January 10, 2006Assignee: Nalco Energy Services, L.P.Inventor: George Richard Meyer
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Patent number: 6699958Abstract: The present invention is directed to compositions and a process leading to colorless or light colored aqueous phicinol-formaldelhyde resoles. Unlike previous technologies, these compositions lead to clear storage stable fast curing, high molecular weight resins. These materials are also capable of producing composite wood panels with superior water absorption and thickness swell test results when soaked in water. The invention essentially consists of an aqueous copolymer of phenol, formaldehyde, and a phenolic carboxylate (e.g. salicylic acid). Methylol phenols are formed under alkaline conditions in the presence of metal chelating agents. These are then condensed into a polymer under alkaline, neutral or acidic conditions. The finished aqueous polymer solution is then acidified to the desired pH using a benzoic acid or a phelnol-carboxylic acid.Type: GrantFiled: February 13, 2003Date of Patent: March 2, 2004Assignee: Borden Chemical, Inc.Inventor: William D. Detlefsen
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Patent number: 6620901Abstract: A high-carbon-yield resole by reacting formaldehyde and excess phenol to an endpoint and then cross-linking with HMTA. Similar high-carbon-yield resoles result with addition of DBE-2, furfuryl alchol and furfural.Type: GrantFiled: December 14, 2001Date of Patent: September 16, 2003Assignee: Borden Chemical, Inc.Inventor: Jimmy Pingao Chen
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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: 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: 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: 5886134Abstract: The invention relates to a Bismaleimide-Triazine resin (BT resin ) and production method thereof and in particular, a series of novel BT resin prepared by reacting a novel bismaleimide with various aromatic cyanate esters. By combining said novel bismaleimide monomer with various proportions of cyanate esters having different structures, BT resins having various processing temperature conditions can be formulated, which, after polymerizing and crosslinking, can provide materials with various thermal stability, dielectric constants, and mechanical properties for various applications.Type: GrantFiled: October 6, 1997Date of Patent: March 23, 1999Assignee: National Science Council of Republic of ChinaInventors: Chun-Shan Wang, Haan-Jang Hwang
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Patent number: 5847058Abstract: 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: GrantFiled: April 5, 1996Date of Patent: December 8, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5834581Abstract: A process for making polyimide-polyamic ester copolymer composition comprisingreacting at least one diamine, a pyromellitic diacid diester compound; at least one other tetracarboxylic diacid diester compound and a selected phosphoramide in the presence of a base catalyst to form a polyimide-polyamic acid ester copolymer.Type: GrantFiled: April 15, 1997Date of Patent: November 10, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ahmad Naiini, Steve L. C. Hsu, William D. Weber, Andrew J. Blakeney
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Patent number: 5756599Abstract: A process for producing a phenol-aldehyde (e.g., cresol-aldehyde) resin that is modified with a dihydroxybenzene compound. The resin may form a binder system when combined with a curing agent which includes an additional source of an aldehyde. The resin and adhesive are useful in the production of wood composite articles by a steam injection process.Type: GrantFiled: July 7, 1997Date of Patent: May 26, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5650478Abstract: A liquid binding agent comprised of a phenolic resin, thinning agents and a curing agent, characterized in that the phenolic resin is produced by condensation catalyzed under alkaline conditions of a phenol and formaldehyde in a molar ratio of phenolic compound to formaldehyde in the range of 1:0.05 to 1.Type: GrantFiled: June 26, 1995Date of Patent: July 22, 1997Assignee: Bakelite AGInventors: Achim Hansen, Michael Konig, Stephan Schroter, Josef Suren
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Patent number: 5637658Abstract: A process for the production of a modified phenol-aldehyde resin which may form a binder system when combined with a curing agent which includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The inventive phenol-aldehyde resin may be modified with compounds from one of the following classes: (1) dihydroxybenzenes, (2) arninophenols, and (3) phenylenediamines. The resin and adhesive are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).Type: GrantFiled: May 23, 1995Date of Patent: June 10, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5594098Abstract: 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: July 11, 1994Date of Patent: January 14, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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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: 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: 5512641Abstract: What is disclosed an aromatic oligoimine having a recurring unit composed of an aromatic dialdehyde having a phenolic hydroxyl group and an aromatic diamine and a number-average degree of polymerization of 2 to 20 and a process for preparing the same, and an aromatic polyimine made by thermally dehydrating the aromatic oligoimine and a process for preparing the same.Type: GrantFiled: March 24, 1995Date of Patent: April 30, 1996Assignee: Arakawa Kagaku Kogyo Kabushiki KaishaInventor: Yoichiro Ezaki
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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: 5264500Abstract: A thermosetting resin designated a "APT" resin is produced by a two-step procedure in which a substituted aromatic compound, preferably diphenyl ether is reacted with formaldehyde to produce an oligomeric backbone, followed by further reaction with a phenol to provide pendant phenolic groups. Finally, the resulting polymer is cyanated with a cyanogen halide.Type: GrantFiled: July 30, 1991Date of Patent: November 23, 1993Assignee: Allied-Signal Inc.Inventors: George D. Green, William B. Bedwell, Raymond J. Swedo
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Patent number: 5264535Abstract: A resin is prepared by the reaction of a phenol, an aldehyde and an aliphatic hydroxy compound containing two or more hydroxy groups per molecule in the presence of a divalent metal ion catalyst. These resins react with polyisocyanates to form polyurethanes that are useful binders for foundry cores and molds.Type: GrantFiled: November 16, 1992Date of Patent: November 23, 1993Assignee: Acme Resin Corp.Inventors: Michael M. Geoffrey, Robert A. Laitar
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Patent number: 5242957Abstract: A binder composition for producing articles of bonded particulate material such as foundry molds or cores comprises an alkaline aqueous solution of a resol phenol-aldehyde resin, an oxyanion which can form a stable complex with the resin, and a phenyl ethylene glycol ether. The binder composition has an alkali to phenol molar ratio of from 1.5:1 to 2.5:1 and the amount of alkali present in the solution is sufficient to substantially prevent stable complex formation between the resin and the oxyanion. Bonded articles are produced by passing carbon dioxide gas through articles formed from a mixture of particulate material and the binder composition so as to produce stable complex formation and curing of the resin.Type: GrantFiled: February 13, 1992Date of Patent: September 7, 1993Assignee: Foseco International LimitedInventors: Garry Smith, Martin Bradley
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Patent number: 5212266Abstract: A catalyst component useful in propylene polymerization in combination with a dialkyl aluminum halide cocatalyst comprises the product of reaction of TiCl.sub.3 which is substantially free of extraneous halide with a selected electron donor compound which is dissolved in a liquid hydrocarbon solvent in which the TiCl.sub.3 is dispersed. The electron donor compound is selected from certain organic acid esters, hindered phenolic compounds and silyl esters.The catalyst of the invention provides increased activity, molecular weight control, increased isotacticity of propylene polymer products and prevents catalyst feed line pluggage, among other advantages.Type: GrantFiled: March 30, 1992Date of Patent: May 18, 1993Assignee: Quantum Chemical CorporationInventors: Charles K. Buehler, Cindy S. Senger, Kenneth W. Johnson
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Patent number: 5189079Abstract: A resin is prepared by the reaction of a phenol, an aldehyde and an aliphatic hydroxy compound containing two or more hydroxy groups per molecule in the presence of a divalent metal ion catalyst. These resins react with polyisocyanates to form polyurethanes that are useful binders for foundry cores and molds.Type: GrantFiled: June 12, 1991Date of Patent: February 23, 1993Assignee: Acme Resin Corp.Inventors: Michael M. Geoffrey, Robert A. Laitar
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Patent number: 5182357Abstract: One hundred percent thermosetting phenol/formaldehyde (P/F) resin and method of preparation thereof are disclosed. The resin comprises a molar ratio of F/P of about 1.2-1.7, has a softening point of about 80.degree. C. and cures at temperature of about 140.degree.-160.degree. C. The method comprises heating the reactants in a solvent-less system in the presence of an ortho directing catalyst while monitoring the amount of free formaldehyde present in the reaction system.Type: GrantFiled: October 22, 1991Date of Patent: January 26, 1993Assignee: DAP, Inc.Inventor: Gary L. Linden
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Patent number: 5155164Abstract: Products of the condensation of phenolmonosulfonic acids, dihydroxydiphenyl sulfones, urea and formaldehyde can be obtained by(A) preparing a homogeneous reaction mixture in sulfuric acid from the phenolmonosulfonic acid and dihydroxydiphenyl sulfone in the molar ratio of from 3:1 to 10:1, with the proviso that the water content of the mixture is not more than 10% of the total weight of the components, and the mixture contains from 0.3 to 1.5 moles of sulfuric acid per mole of dihydroxydiphenyl sulfone, at from 100.degree. to 180.degree. C.,(B) subsequently, at from 40.degree. to 90.degree. C., carrying out a precondensation with 1 to 2 moles of formaldehyde and 0.5 to 1.5 moles of urea per mole of phenol units present in aqueous medium,(C) partially neutralizing the reaction mixture,(D) adding to the partially neutralized reaction mixture 0 to 0.5 mole of phenol per mole of phenol units present and then 0.1 to 0.8 mole of formaldehyde per mole of phenol units then present,(E) further condensing at from 40.Type: GrantFiled: May 8, 1991Date of Patent: October 13, 1992Assignee: BASF AktiengesellschaftInventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
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Patent number: 5151496Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: December 18, 1991Date of Patent: September 29, 1992Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
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Patent number: 5109078Abstract: The present invention is a cyanato group containing phenolic resin of the formula: ##STR1## wherein n is 0 or an integer of one or more, and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The advancement over the art is that the resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 1 minute, preferably greater than 2 minutes, more preferably greater than 10 minutes, and most preferably greater than 20 minutes at 155.degree. C. Alternately, the improved resin of the present invention can be characterized as having a thermal stability indicated by thermal decomposition temperature of at least 400.degree. C. and preferably of at least 450.degree. C. as measured by Thermal Gravimetric Analysis (TGA).Type: GrantFiled: April 1, 1991Date of Patent: April 28, 1992Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 5043412Abstract: A raw batch composition for use in making a shaped article such as a foundry shape or refractory article is disclosed. The composition comprises a mixture of an aggregate material; a phenol formaldehyde novolak resin; a phenol formaldehyde resole resin; and an ester functional curing agent. A shaped article prepared from the composition and processes for making a refractory body or foundry article are also disclosed.Type: GrantFiled: September 1, 1989Date of Patent: August 27, 1991Assignee: Borden, Inc.Inventors: Pitchaiya Chandramouli, Raja Iyer, Calvin Johnson
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Patent number: 5021474Abstract: Moulding compositions comprising(a) a melamine/formaldehyde resin, a melamine/phenol/formaldehyde resin or a mixture of said resins,(b) organic and/or inorganic fillers,(c) a lubricant, and(d) 0.1 to 2% by weight, based on the total composition, of 3-chloro-1,2-propanediol as latent hardener,are suitable for the production of mouldings by injection moulding. The latent hardener employed permits extremely short cycle times coupled with long residence times at the cylinder temperature of the injection moulding machine. The moulding compositions are distinguished at the same time by very good flow properties.Type: GrantFiled: February 26, 1990Date of Patent: June 4, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Gunther, Hermann O. Wirth, Wilhelm Endlich
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Patent number: 5004788Abstract: The present invention is a cyanato group containing phenolic resin of the formula: ##STR1## wherein n is 0 or an integer of one or more, and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The advancement over the art is that the resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 1 minute, preferably greater than 2 minutes, more preferably greater than 10 minutes, and most preferably greater than 20 minutes at 155.degree. C. Alternately, the improved resin of the present invention can be characterized as having a thermal stability indicated by thermal decomposition temperature of at least 400.degree. C. and preferably of at least 450.degree. C. as measured by Thermal Gravimetric Analysis (TGA).Type: GrantFiled: March 1, 1989Date of Patent: April 2, 1991Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 4988780Abstract: The present invention is flame resistant article and related method, made of phenolic triazine resin derived from a cyanato group containing phenolic resin of the formula: ##STR1## wherein: n is a positive whole number greater than or equal to 1;q and r are the same or different at each occurrence and are whole numbers from 0 to 3, with the proviso that the sum of q and r at each occurrence is equal to 3;Z is --CN, or hydrogen and --CN;o and p are the same or different at each occurrence and are whole numbers from 0 to 4 with the proviso that the sum of o and p at each occurrence is equal to 4;--X-- is a divalent organic radical; andR.sub.3 is the same or different at each occurrence and is a substituent other than hydrogen which is unreactive under conditions necessary to completely cure the copolymer.Type: GrantFiled: August 15, 1988Date of Patent: January 29, 1991Assignee: Allied-SignalInventors: Sajal Das, Dusan C. Prevorsek, Raj Sharma, Bruce DeBona
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Patent number: 4987198Abstract: There is provided thermosetting resin compositions suitable for injection molding compounds having an apparent curing rate of 0.7 and 0.008 cm/sec respectively at 170.degree. C. and 110.degree. C. by a disk cure tester and an apparent activation energy of at least 26 Kcal/mol, by the addition of fluidity modifiers selected from ether compounds having methylene ether type structure, ester compounds having methylene groups connected with carbonyl ether groups and alcohol compounds having methylene groups connected with hydroxyl groups, to phenolic resin, hexamethylenetetramine, fillers and additives.Type: GrantFiled: October 24, 1988Date of Patent: January 22, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tsukuru Izukawa, Shuhei Ikado, Toshiyuki Enomoto
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Patent number: 4978727Abstract: The present invention is a cyanato group containing phenolic resin, and method to prepare the resin. The resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 1 minute, preferably greater than 2 minutes, more preferably greater than 10 minutes. The resin has substantially no smoke generation during gel time measurement at 155.degree. C.Type: GrantFiled: April 12, 1988Date of Patent: December 18, 1990Assignee: Allied-SignalInventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 4977231Abstract: Carbamate curing agents for phenol-aldehyde resins provide a delayed curing period for product assembly. Thereafter, the resin cures quickly even at low temperatures.Type: GrantFiled: April 13, 1989Date of Patent: December 11, 1990Assignee: Georgia-Pacific CorporationInventors: Ted M. McVay, Gene F. Baxter
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Patent number: 4970276Abstract: Phenolic cyanate/phenolic triazine copolymers and cured resins prepared therefrom.Type: GrantFiled: May 26, 1989Date of Patent: November 13, 1990Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 4961795Abstract: A composition and a process for bonding lignocellulosic material under heat and pressure is disclosed. According to the process, a curing agent is combined with a binder which is an alkaline phenol-formaldehyde resin. In one aspect the combination is by injection into a line carrying the binder to application apparatus, followed by in-line mixing of the curing agent and binder and application of the mixture to the lignocellulosic material. The lignocellulosic material is then compressed and the binder cured. The curing agent may be an ester, a lactone or an organic carbonate. The effect of the curing agent may be moderated with an aliphatic mono or polyhydric alcohol.Type: GrantFiled: January 27, 1988Date of Patent: October 9, 1990Assignee: Borden, Inc.Inventors: William D. Detlefsen, Earl K. Phillips, Richard V. Norton
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Patent number: 4925887Abstract: Moulding compositions comprising(a) a melamine/formaldehyde resin, a melamine/phenol/formaldehyde resin or a mixture of said resins,(b) organic and/or inorganic fillters,(c) a lubricant, and(d) 0.1 to 2% by weight, based on on the total composition, of 3-chloro-1,2-propanediol as latent hardener,are suitable for the production of mouldings by injection moulding. The latent hardener employed permits extremely short cycle times coupled with long residence times at the cylinder temperature of the injection moulding machine. The moulding compositions are distinguished at the same time by very good flow properties.Type: GrantFiled: April 7, 1989Date of Patent: May 15, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Gunther, Hermann O. Wirth, Wilhelm Endlich
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Patent number: 4876324Abstract: Orthocresol or a mixture of orthocresol and paracresol and an aldehyde compound or a derivative thereof are subjected to polycondensation in a solvent selected from an aliphatic alcohol having 3 to 12 carbon atoms, a glycol ether having 3 to 6 carbon atoms, benzyl alcohol and an aliphatic carboxylic acid having 2 to 6 carbon atoms, in the presence of an acid catalyst, to obtain linear and high molecular weight orthocresol-novolak resins or orthocresol/paracresol random copolymerized novolak resins which have a high softening point of 145.degree. C. or higher and a high number average molecular weight of 1500 or more and which are highly soluble in alcohols and ketones and are highly compatible with resins.Type: GrantFiled: May 13, 1987Date of Patent: October 24, 1989Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Yoshitomo Nakano, Masumi Kada
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Patent number: 4857624Abstract: Improved phenolic-modified rosin ester resins are disclosed. The phenolic-modified rosin ester resins comprise the reaction product of substantially unsaturated rosins with a dienophile, a phenolic compound and a formaldehyde-containing compound, which product is then esterified. The resulting composition is useful in vehicles for publication gravure printing inks, as well as in the printing inks themselves. Printing inks fabricated in accordance with the invention employing these improved phenolic-modified rosin ester resins provide prints of superior quality.Type: GrantFiled: May 27, 1988Date of Patent: August 15, 1989Assignee: BASF CorporationInventors: Douglas S. DeBlasi, John P. Walsh
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Patent number: 4851279Abstract: The present invention is a fiber comprising cyanato group containing phenolic resin comprising repeating units of the formula: ##STR1## wherein p is 0 or an integer of one or more, q is 0 or an integer of 1 or more, X is a radical selected from the group consisting of: --CH.sub.2 --, --CO--, --SO.sub.2 --, ##STR2## and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The fiber of the present invention can be made a phenolic triazine derived from the cyanato group containing phenolic resin.Type: GrantFiled: December 21, 1987Date of Patent: July 25, 1989Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 4831086Abstract: The present invention is a cyanato group containing phenolic resin of the formula: ##STR1## wherein n is 0 or an integer of one or more, and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The advancement over the art is that the resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 1 minute, preferably greater than 2 minutes, more preferably greater than 10 minutes, and most preferably greater than 20 minutes at 155.degree. C. Alternately, the improved phenolic triazine resin of the present invention can be characterized as having a thermal stability indicated by thermal decomposition temperature of at least 400.degree. C. and preferably of at least 450.degree. C. as measured by Thermal Gravimetric Analysis (TGA).Type: GrantFiled: October 5, 1987Date of Patent: May 16, 1989Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 4698401Abstract: A polyfunctional reaction product having functional phenolic OH groups is made available by reacting a phenol and an alkoxylated amino-aldehyde condensation product in the presence of a solvent and of an acid catalyst. This method makes it possible to prepare a polyfunctional phenolic reaction product which is soluble in organic solvents at a low ratio of phenolic OH groups to alkoxy groups without gelling. The reaction product is particularly useful as a curing agent for epoxy resins.Type: GrantFiled: September 9, 1985Date of Patent: October 6, 1987Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Raymond Koenig
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Patent number: 4675375Abstract: Essentially phenol-free phenol resol ethers which are bonded via o,o'-methylene ether groups are prepared by a process in whichA. where the process is carried out beginning with the methylolation in an aqueous medium, the methylolation is carried out in the presence of 0.5-10% by weight, based on the phenol employed, of Me.sup.++ ions, the latter are then removed as a sparingly soluble salt, the water present as a solvent in the reaction mixture is removed at 30.degree.-80.degree. C. in the presence or absence of one or more monohydric, dihydric or trihydric alcohols and an entraining agent, and the water of reaction formed during the etherification is separated off at 45.degree.-120.degree. C., andB. where the process is carried out beginning with the methylolation in a non-polar organic solvent, the methylolation is carried out in the presence of 0.1-0.3% by weight, based on the phenol employed, of Me.sup.++ ions, the etherification is effected at 95.degree.-120.degree. C.Type: GrantFiled: June 13, 1985Date of Patent: June 23, 1987Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Juergen Nieberle
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Patent number: 4657950Abstract: Refractory shaped articles are prepared by heating refractory mixes comprised of refractory particles and an alkoxy modified phenolic resole resin having at least one alkoxy methylene group for every 20 phenolic hydroxyl groups.Type: GrantFiled: October 12, 1984Date of Patent: April 14, 1987Assignee: Acme Resin CorporationInventors: Raja Iyer, Rasik C. Shah, Robert A. Laitar