With Nitrogen-containing Reactant Patents (Class 528/162)
  • Patent number: 5756599
    Abstract: 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: Grant
    Filed: July 7, 1997
    Date of Patent: May 26, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5756592
    Abstract: A continuous process for the production of a phenolic-based cyanate ester resin is provided and includes the steps of: feeding a phenolic organic compound, a trialkylamine and a cyanogen halide into a continuous, plug-flow type reactor; causing the reactants to flow through and react in the reactor over a period of time defined as a residence time; continuously reacting the phenolic organic compound, the triallckylamine and the cyanogen halide in the reactor; and maintaining a temperature in the reactor of between about -75.degree. C. to about 0.degree. C. The reactor has a length which is equal to or greater than ten times its internal diameter. The mol equivalent concentration of the cyanogen halide is greater than the mol equivalent concentration of the trialkylamine, and the mol equivalent of the trialkylamine is greater than the mol equivalent of the phenolic organic compound.
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: May 26, 1998
    Assignee: AlliedSignal, Inc.
    Inventors: William B. Bedwell, Raymond J. Swedo, Bruce T. DeBona, George D. Green
  • Patent number: 5721332
    Abstract: A phenolic resin obtained by reacting a phenol with an aromatic aldehyde and a xylylene compound represented by the formulaROH.sub.2 C(C.sub.6 H.sub.4)CH.sub.2 ORwhere R is hydrogen, an alkyl group having a carbon atom number of 1-4, or an acyl group having a carbon atom number of 2-4 in the presence of acid catalyst, with the sum of aromatic aldehydes and xylylene compounds to phenols molar ratio being 0.1-0.95, and the xylylene compounds to aromatic aldehydes molar ratio being 0.1-1.4.The phenolic resin thus obtained is useful as an industrial material by virtue of its excellent moisture resisting property, alkali resistance and fair thermosetting property. Having low moisture absorption ratio and high glass transition temperature, this phenolic resin is also suitable used as hardener for semiconductor encapsulating epoxy resin which has excellent package crack resistance after solder dipping and high reliability.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: February 24, 1998
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Haruyuki Kano, Yoshihisa Sone, Kouichi Yoshimura, Hiroichi Kouyama
  • Patent number: 5672674
    Abstract: Polyamide-containing fibre materials can be given an anti-stain finish by treating them with a sulpho-containing aromatic formaldehyde condensation product in combination with polyacrylic acid, the treatment with the two components being carried out in any desired order or simultaneously.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Walz, Udo Winfried Hendricks, Hans-Albert Ehlert
  • Patent number: 5659002
    Abstract: The invention is a process for preparing alkylated tannin Mannich polymers by reacting a tannin Mannich condensation polymer, prepared from a condensed tannin, and amine, and formaldehyde, with an alkylating agent at a pH between 5 and 14. Optionally, the alkylated tannin Mannich polymer may be reacted further with formaldehyde to increase its viscosity.The invention further comprises a method of removing color form waste water utilizing the alkylated tannin Mannich polymer produced by the above process.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: August 19, 1997
    Assignee: Nalco Chemical Company
    Inventors: Peter E. Reed, Martha R. Finck
  • Patent number: 5646219
    Abstract: 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) aminophenols, and (3) phenylenediamines. The resin and adhesive are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5639396
    Abstract: A process for producing an oil soluble interpolymer polymer of 1,2-alkylenediamine such as N-ethyl ethylenediamine, aldehyde-provider such as formaldehyde, and ortho-unsubstituted hydroxyaromatics such as 4-polyalkylene phenol is disclosed. The decyclized Mannich Base monomer units provide a higher viscosity material which is suitably substituted with a long chain hydrocarbyl para substituent such as polyisobutylene or ethylene/alpha-olefin polymer. Various ortho-substituted hydroxyaromatics such as o-cresol may be used to control the degree of polymerization. The polymers are useful as dispersants or other lubricant additives.
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: June 17, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Warren A. Thaler, Stephen Zushma, Antonio Gutierrez
  • Patent number: 5637658
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: June 10, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5623032
    Abstract: A process for preparing ashless and low-ash phenolic resole resins having no amine odor, and a process for preparing storage-stable mixtures or premix solutions of phenol-formaldehyde resin and urea or unrea-formaldehyde resins. These processes react phenol and formaldehyde in the presence of an effective catalytic amount of a low-volatile and strongly basic tertiary amino alcohol either alone or in combination with an inorganic base.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: April 22, 1997
    Assignee: Angus Chemical Company
    Inventor: Gaoming Wu
  • Patent number: 5608029
    Abstract: A process for producing an oil soluble interpolymer polymer of 1,2-alkylenediamine such as N-ethyl ethylenediamine, aldehyde-provider such as formaldehyde, and ortho-unsubstituted hydroxyaromatics such as 4-polyalkylene phenol is disclosed. The decyclized Mannich Base monomer units provide a higher viscosity material which is suitably substituted with a long chain hydrocarbyl para substituent such as polyisobutylene or ethylene/alpha-olefin polymer. Various ortho-substituted hydroxyaromatics such as o-cresol may be used to control the degree of polymerization. The polymers are useful as dispersants or other lubricant additives.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: March 4, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Warren A. Thaler, Stephen Zushma, Antonio Gutierrez
  • Patent number: 5589553
    Abstract: A resin suitable for use as a photoresist that is the esterification product of an o-quinonediazide compound and an aromatic novolak resin. The aromatic novolak resin may be the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde. The aromatic resin may be chain extended by further reaction with an additional aldehyde. The resin has a maximum of 20 percent of its phenolic hydroxyl groups esterified with the o-quinonediazide sulfonate compound.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: December 31, 1996
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Peter Trefonas, III
  • 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: 5512641
    Abstract: 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: Grant
    Filed: March 24, 1995
    Date of Patent: April 30, 1996
    Assignee: Arakawa Kagaku Kogyo Kabushiki Kaisha
    Inventor: Yoichiro Ezaki
  • Patent number: 5505998
    Abstract: Described is an acidic glass fiber binding composition comprising an aqueous soluble phenol formaldehyde resin having low free formaldehyde, an effective amount of a formaldehyde scavenger, and an effective amount of a strong aqueous soluble acid, wherein the composition has an acidic pH and the solids content ranges from about 1 to about 30% by weight of the total composition. Also described is a method of binding glass fibers such as newly formed warm glass fibers at junctions of the fibers by applying the composition as described above to the fibers and then drying the composition. Also described are B-staged and C-staged glass fiber compositions having a alkylamine content less than 5 ppm.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: April 9, 1996
    Assignee: Schuller International, Inc.
    Inventors: Dale J. Mathews, Philip F. Miele, Edmund G. Dornfeld
  • Patent number: 5492998
    Abstract: Novel polymers of general formula: ##STR1## wherein R is an alkyl or aryl group that contains an active hydrogen atom (as determined by the Zerewitinoff test); A is a spacing group having at least one carbon atom; B is a spacing group having at least two carbon atoms; and R and R' are alkyl or aryl groups. The polymer is synthesized via the Mannich pathway, involving formation of an imine intermediate.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: February 20, 1996
    Assignees: Lifesource International, Ltd., Jojani Inc.
    Inventor: Nicholas M. Irving
  • Patent number: 5426161
    Abstract: 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: Grant
    Filed: May 2, 1994
    Date of Patent: June 20, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 5422221
    Abstract: In a resist composition, a novolak resin including at least one recurring unit of the formula (1): ##STR1## wherein n is an integer of 1 to 4 and m is an integer of 0 to 3, having a weight average molecular weight of 1,000 to 10,000 calculated as polystyrene, and having the hydrogen atom of a hydroxyl group therein replaced by a 1,2-naphthoquinonediazidosulfonyl group in a proportion of 0.03 to 0.27 mol per hydrogen atom serves as an alkali-soluble resin and a photosensitive agent. The composition is uniform in that the photosensitive agent is uniformly incorporated in the novolak resin, and thus forms a uniform resist film. It is a useful positive resist having improved sensitivity, resolution, heat resistance, and film retentivity.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: June 6, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Satoshi Okazaki, Mitsuo Umemura, Hiroshi Kanbara, Jun Hatakeyama, Tetsuya Inukai, Kazuhiro Nishikawa
  • Patent number: 5358748
    Abstract: Described is an acidic glass fiber binding composition comprising an aqueous soluble phenol formaldehyde resin having low free formaldehyde, an effective amount of a formaldehyde scavenger, and an effective amount of a strong aqueous soluble acid, wherein the composition has an acidic pH and the solids content ranges from about 1 to about 30% by weight of the total composition. Also described is a method of binding glass fibers such as newly formed warm glass fibers at junctions of the fibers by applying the composition as described above to the fibers and then drying the composition. Also described are B-staged and C-staged glass fiber compositions having a alkylamine content less than 5 ppm.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: October 25, 1994
    Assignee: Schuller International, Inc.
    Inventors: Dale J. Mathews, Philip F. Miele, Edmund G. Dornfeld
  • Patent number: 5342916
    Abstract: Condensation polymers of sulfonated phenols, urea, other organic nitrogen-bases and formaldehyde, obtainable by(A) sulfonation of phenols with from 1.0 to 1.5 moles of sulfuric acid per mole of phenol and(B) condensation of these sulfonation products with(a) from 0.5 to 1.8 moles of urea per mole of phenol,(b) from 0.001 to 0.5 moles of at least one other organic nitrogen-base per mole of phenol, and(c) from 1.0 to 3.0 moles of formaldehyde per mole of phenol.The condensation polymers are suitable for use as tanning agents in the leather and skin-producing industry and as spraying aids for redispersible polymer powders.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: August 30, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Weiser, Wolfgang Reuther, Karl Stork, Ortwin Schaffer, Gernot Franzmann, Thomas Schwerzel, Maximilian Angel, Joachim Pakusch, Brigitte Wegner
  • Patent number: 5340903
    Abstract: The invention concerns a phenolic resin.The resin is a liquid, contains phenol-formaldehyde, formaldehyde-urea and phenol-formaldehyde-amine condensates, and has a free formaldehyde content of less than 3%, this proportion being expressed as a percentage of the total fluid weight, and a dilutability rate in water which equals or surpasses 1,000%. Furthermore, the resin is stable when heated. Application to less-polluting sizing compositions for mineral fibers; and use of the fibers thus sized for the manufacture of insulating products and soilless cultivation substrates.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: August 23, 1994
    Assignee: Isover Saint-Gobain
    Inventors: M. Serge Tetart, M. David Segal
  • Patent number: 5310855
    Abstract: The aromatic formaldehyde condensation products, which are substantially colorless and water-soluble and contain sulphonate and/or carboxylate groups, are obtainable by adding agents which have a reducing action during and/or after the condensation reaction, and are suitable for the treatment of textiles and leather.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: May 10, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Walz, Udo Hendricks, Hans-Albert Ehlert, Fritz Lesszinsky
  • Patent number: 5302687
    Abstract: A process for preparing a polymeric composition comprising reacting a mixture of at least one phenolic compound and at least one oxazoline compound in the presence of a catalytic amount of at least one ammonium salt and a tetracarbyl phosphonium salt, and optionally also in the presence of an alkyl halide is described.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: April 12, 1994
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba, Gilbert M. Gynn
  • Patent number: 5300593
    Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: April 5, 1994
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5270434
    Abstract: The invention concerns a phenolic resin.The resin is a liquid, contains phenol-formaldehyde, formaldehyde-urea and phenol-formaldehyde-amine condensates, and has a free formaldehyde content of less than 3%, this proportion being expressed as a percentage of the total fluid weight, and a dilutability rate in water which equals or surpasses 1,000%. Furthermore, the resin is stable when heated. Application to less-polluting sizing compositions for mineral fibers; and use of the fibers thus sized for the manufacture of insulating products and soilless cultivation substrates.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: December 14, 1993
    Assignee: Isover Saint-Gobain
    Inventors: M. Serge Tetart, M. David Segal
  • Patent number: 5264500
    Abstract: 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: Grant
    Filed: July 30, 1991
    Date of Patent: November 23, 1993
    Assignee: Allied-Signal Inc.
    Inventors: George D. Green, William B. Bedwell, Raymond J. Swedo
  • Patent number: 5256325
    Abstract: An oil soluble dispersant additive useful in oleaginous compositions selected from fuels and lubricating oils comprising the reaction products of:(i) at least one intermediate adduct comprised of the reaction products of(a) at least one polyanhydride, and(b) at least one member selected from the group consisting of polyamines, polyols, and amino alcohols; and(ii) at least one member selected from the group consisting of(a) at least one long chain hydrocarbyl substituted C.sub.4 -C.sub.10 dicarboxylic acid producing material;(b) at least one long chain hydrocarbyl substituted hydroxy aromatic material and at least one aldehyde; or(c) at least one aldehyde and at least one reaction product of a hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid or anhydride and an amine substituted hydroxy aromatic compound.Also disclosed are oleaginous compositions, particularly lubricating oil compositions, containing these oil soluble dispersants.
    Type: Grant
    Filed: February 2, 1993
    Date of Patent: October 26, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob Emert, Robert D. Lundberg, Antonio Gutierrez
  • Patent number: 5233012
    Abstract: Novel condensates comprising bisphenols and aromatic aminosulfonic acids, in particular, novel 4-aminobenzenesulfonic acid-2,2-bis (hydroxyphenyl)propaneformaldehyde condensates, and methods for their production are disclosed. The novel condensates are useful as a dispersant for disperse dyes, an additive for carbonaceous fine powder-water slurries and as a water reducing agent for cement.
    Type: Grant
    Filed: June 8, 1992
    Date of Patent: August 3, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Masanobu Kawamura, Shinji Hamada, Takashi Date, Toshihiro Sugiwaki, Nobuhiro Hanada
  • Patent number: 5194331
    Abstract: 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 O 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: Grant
    Filed: September 16, 1991
    Date of Patent: March 16, 1993
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 5155164
    Abstract: 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: Grant
    Filed: May 8, 1991
    Date of Patent: October 13, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
  • Patent number: 5136011
    Abstract: The present invention features a highly oriented, triazine superstructural network, whose structural alignment is magnetically induced in the liquid crystalline phase during the curing process of its liquid crystalline cyanate ester precursor. High mechanical strength cross-linked network structures are prepared from a new class of liquid crystalline dicyanate compounds. Optionally ring substituted di-(4-hydroxyphenyl)-terephthalate is synthesized as a precursor in the preparation of highly structured triazine networks. The orientation of the triazine networks has been accomplished by magnetically aligning the liquid crystalline phase of the precursor during the curing reaction.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: August 4, 1992
    Assignees: Cornell Research Foundation, International Business Machines Corporation
    Inventors: George G. Barclay, Christopher K. Ober, Konstantinos I. Papathomas, David W. Wang
  • Patent number: 5130385
    Abstract: The present invention is a cyanato group containing phenolic resin, and to phenolic triazine resins derived therefrom. The cyanato group containing phenolic resin of the present invention can be completely cured to form a phenolic triazine resin having a glass transition temperature equal to or greater than 250.degree. C.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: July 14, 1992
    Assignee: Allied-Signal Inc.
    Inventor: Sajal Das
  • Patent number: 5126412
    Abstract: The present invention is a cyanato group containing phenolic resin, and to phenolic triazine resins derived therefrom. The resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 3 minutes and by a shelf life equal to or greater than 3 days.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: June 30, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 5124414
    Abstract: Phenolic cyanate/phenolic triazine copolymers and cured resins prepared therefrom.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: June 23, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Das Sajal, Dusan C. Prevorsek
  • Patent number: 5120817
    Abstract: An epoxy resin composition comprises an vicinal polyepoxide and a Mannich condensation reaction product curing agent. The curing agent is the Mannich condensation reaction product of a phenol, formaldehyde and a polyoxyethylenediamine of the formula:NH.sub.2 (CH.sub.2 CH.sub.2 O).sub.x --CH.sub.2 CH.sub.2 NH.sub.2,and wherein: x ranges from 1 to 3. These epoxy resin compositions are useful in coatings, adhesives, encapsulations and composite matrices.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: June 9, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Harold G. Waddill, Jiang-Jen Lin
  • Patent number: 5120815
    Abstract: An improved process for preparing Mannich polyols is disclosed. The process involves capping a Mannich condensate of a phenolic compound or an amino-substituted s-triazine with a small quantity of an alkylene oxide in the absence of an alkylene oxide polymerization catalyst, prior to heating the condensate to elevated temperatures at which polycondensates are formed. The capped Mannich condensate is then alkoxylated to form the desired polyol.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: June 9, 1992
    Assignee: The Dow Chemical Company
    Inventors: John E. Marugg, Michael A. P. Gansow, Johan A. Thoen
  • Patent number: 5109078
    Abstract: 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: Grant
    Filed: April 1, 1991
    Date of Patent: April 28, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 5101001
    Abstract: This invention relates to no-bake foundry binders and a no-bake process for preparing foundry shapes which utilizes polyurethane-forming foundry binders. The binders are unique because the isocyanate component preferably contains no solvent and the weight ratio of the phenolic resin component to isocyanate component is atypical. It has been found that the use of these binders in a no-bake process produces foundry shapes with improved tensile strengths.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: March 31, 1992
    Assignee: Ashland Oil, Inc.
    Inventors: Colleen M. Henry, Richard L. Smith
  • Patent number: 5098986
    Abstract: Normally liquid polyfunctional final Mannich condensates that are useful as curing agents for epoxy resins are prepared by reacting a para C.sub.1 -C.sub.15 alkyl phenol with formaldehyde and a first polyoxyalkylene diamine to form an intermediate Mannich condensate that is reacted, in turn, with formaldehyde and a second polyoxyalkylene diamine to form the final Mannich condensate, the first polyoxyalkylene diamine having the formula: ##STR1## wherein: n represents a positive number having a value of 1 to about 6, andR' independently represents hydrogen or a methyl group, the second polyoxyalkylene diamine having the formula: ##STR2## wherein n and n' represent positive numbers having a value of 1 to about 6,R' independently represents hydrogen or a methyl group, andR"' represents an alkyl group containing 1 to 4 carbon atoms or a cyanoethyl group.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: March 24, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Jiang-Jen Lin
  • Patent number: 5082920
    Abstract: Improvements in the thermal stability of bis(isoimide) resins are achieved by the addition of small amounts of trihydroxyaromatic or polyhydroxyaromatic compounds to the partially polymerized bis(isoimide) resin composition.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: January 21, 1992
    Inventor: John D. Harper
  • Patent number: 5047160
    Abstract: An oil soluble dispersant additive useful in oleaginous compositions selected from fuels and lubricating oils comprising the reaction products of:(i) at least one intermediate adduct comprised of the reaction products of(a) at least one polyanhydride, and(b) at least one member selected from the group consisting of polyamines, polyols, and amino alcohols; and(ii) at least one member selected from the group consisting of(a) at least one long chain hydrocarbyl substituted C.sub.4 -C.sub.10 dicarboxylic acid producing material;(b) at least one long chain hydrocarbyl substituted hydroxy aromatic material and at least one aldehyde; or(c) at least one aldehyde and at least one reaction product of a hydrocarbyl substituted C.sub.3 -C.sub.10 monocarboxylic or C.sub.4 -C.sub.10 dicarboxylic acid or anhydride and an amine substituted hydroxy aromatic compound.Also disclosed are oleaginous compositions, particularly lubricating oil compositions, containing these oil soluble dispersants.
    Type: Grant
    Filed: December 29, 1988
    Date of Patent: September 10, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob Emert, Robert D. Lundberg, Antonio Gutierrez
  • Patent number: 5043365
    Abstract: A granular molding material with a binder comprising a phenol novolac and a polyisocyanate which hardens upon addition of amine catalysts wherein the molar ratio of phenol to formaldehyde in the novolac is 1:0.25 to 1:0.5 and has the formula ##STR1## wherein R, R' and R" are individually selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, hydroxy, cycloalkyl of 3 to 12 carbon atoms and an anellated ring and X is an integer from 0 to 4 or >4 with the percent molar distribution based on X is as follows:______________________________________ when X = 0: 20-55% X = 1: 15-30% X = 2: 10-30% X = 3: 0-50% X .gtoreq. 4: 0-2.5% ______________________________________for the production of improved foundry cores and molds.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: August 27, 1991
    Assignee: Rutgerswerke AG
    Inventors: Arno Gardziella, Alois Kwasniok, Peter Adolphs, Ralf Wetzig
  • Patent number: 5043412
    Abstract: 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: Grant
    Filed: September 1, 1989
    Date of Patent: August 27, 1991
    Assignee: Borden, Inc.
    Inventors: Pitchaiya Chandramouli, Raja Iyer, Calvin Johnson
  • Patent number: 5004788
    Abstract: 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: Grant
    Filed: March 1, 1989
    Date of Patent: April 2, 1991
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4988780
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: January 29, 1991
    Assignee: Allied-Signal
    Inventors: Sajal Das, Dusan C. Prevorsek, Raj Sharma, Bruce DeBona
  • Patent number: 4978727
    Abstract: 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: Grant
    Filed: April 12, 1988
    Date of Patent: December 18, 1990
    Assignee: Allied-Signal
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4977231
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: December 11, 1990
    Assignee: Georgia-Pacific Corporation
    Inventors: Ted M. McVay, Gene F. Baxter
  • Patent number: 4973649
    Abstract: Novel thermosetting imido prepolymers having low melt viscosity, well adapted for the production, e.g., of preimpregnated shaped articles, are copolymerizates of at least one N,N'-bismaleimide; at least one hindered diprimary diamine, e.g., 4,4'-diamino-3,3',5,5'-tetraalkyl-diphenyl-methane or 1,3-diamino- or 1,4-diaminotrialkylbenzene; at least one comonomeric heterocycle, e.g., a vinylpyridine, N-vinyl-2-pyrrolidone, allyl isocyanurate, vinyltetrahydrofuran, and/or an imidazole compound; and at least one comonomeric (meth)acrylate.
    Type: Grant
    Filed: March 3, 1989
    Date of Patent: November 27, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventor: Yves Camberlin
  • Patent number: 4970276
    Abstract: Phenolic cyanate/phenolic triazine copolymers and cured resins prepared therefrom.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: November 13, 1990
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4944812
    Abstract: A vegetable tannin is condensed with formaldehyde and an amine to provide an acid soluble product which is useful in a metal treatment solution to enhance corrosion resistance and paint adhesion characteristics of a metal surface.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: July 31, 1990
    Assignee: Henkel Corporation
    Inventors: Andreas Lindert, Stephen M. Wolpert
  • Patent number: 4904516
    Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: February 27, 1990
    Inventor: Albert W. Creamer