Nitrogen-containing Material Contains A Nitrogen Atom Directly Bonded To A Carbon Atom Patents (Class 528/146)
  • Patent number: 10280359
    Abstract: Methods of using a component in a subterranean wellbore include positioning a component including a degradable thermoset polymer material in a wellbore location, obstructing flow with the component, exposing the component to an acidic solution to degrade the selectively degradable thermoset polymer material and to remove the component from the wellbore location, and flowing a fluid through the wellbore location where the component was positioned. Methods of forming a component of a wellbore system include forming at least a portion of the component to comprise a degradable thermoset polymer material. Wellbore systems include at least one component including a selectively degradable thermoset polymer material. The selectively degradable thermoset polymer material may be a polyhexahydrotriazine (“PHT”) material.
    Type: Grant
    Filed: December 27, 2017
    Date of Patent: May 7, 2019
    Assignee: Baker Hughes Incorporated
    Inventors: Anil K. Sadana, Jeffrey R. Potts
  • Patent number: 9040650
    Abstract: A method for preparing a formaldehyde-free phenolic plastic resin, includes a step of preparing a hardener via careful oxidation of a polyol and a step of reacting the hardener with phenolic compounds.
    Type: Grant
    Filed: November 19, 2010
    Date of Patent: May 26, 2015
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE MONTPELLIER
    Inventors: Sylvain Caillol, Bernard Boutevin, Ghislain David, Carine Burguiere
  • Patent number: 8791214
    Abstract: A low dielectric constant, a low dielectric loss tangent, and heat resistance are achieved. An active ester resin that has a resin structure produced by reacting a polyfunctional phenolic compound (a1) with a monofunctional aromatic carboxylic acid or its chloride (a2) and an aromatic dicarboxylic acid or its chloride (a3). The polyfunctional phenolic compound (a1) is represented by structural formula (1) below: (where Ar represents a benzene ring, a naphthalene ring, a benzene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, or a naphthalene ring nuclear-substituted by an alkyl group having 1 to 4 carbon atoms, X represents a methylene group, a divalent cyclic aliphatic hydrocarbon group, a phenylene dimethylene group, or a biphenylene-dimethylene group, and n represents the number of repeating units and the average thereof is in a range of 0.5 to 10).
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: July 29, 2014
    Assignee: DIC Corporation
    Inventors: Kan Takeuchi, Etsuko Suzuki, Kunihiro Morinaga, Kazuo Arita
  • Publication number: 20120277396
    Abstract: A method for preparing a formaldehyde-free phenolic plastic resin, includes a step of preparing a hardener via careful oxidation of a polyol and a step of reacting the hardener with phenolic compounds.
    Type: Application
    Filed: November 19, 2010
    Publication date: November 1, 2012
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), ECOLE NATIONALE SUPERIEURE DE CHIMMIE DE MONTPELLIER, UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES
    Inventors: Sylvain Caillol, Bernard Boutevin, Ghislain David, Carine Burguiere
  • Publication number: 20120271028
    Abstract: Resol beads are disclosed that are prepared in high yield by reaction of a phenol with an aldehyde, with a base as catalyst, a colloidal stabilizer, and optionally a surfactant. The resol beads have a variety of uses, and may be thermally treated and carbonized to obtain activated carbon beads.
    Type: Application
    Filed: July 3, 2012
    Publication date: October 25, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Charles Edwan Sumner, Ramesh Chand Munjal, Ruairi Seosamh O'Meadhra, Chester Wayne Sink, Jerry Steven Fauver, Robert Melvin Schisla, Shriram Bagrodia, Spencer Erich Hochstetler, Tera Jill Hardin
  • Patent number: 8017562
    Abstract: Phosphate esters useful for gelling hydrocarbons in combination with a metal source are disclosed along with methods of preparation of the phosphate esters. Fouling in oil refinery towers has been attributed due to distillation of impurities present in phosphate esters used to gel hydrocarbons for oil well fracturing. The improved method of preparation of the phosphate ester results in a product that substantially reduces or eliminates volatile phosphorus, which is phosphorus impurities that distill up to 250° C., and increases the high temperature viscosity of the hydrocarbon gels formed using the phosphate esters.
    Type: Grant
    Filed: November 5, 2010
    Date of Patent: September 13, 2011
    Assignee: Brine-Add Fluids Ltd.
    Inventors: David P. Horton, Ioan Ghesner
  • Publication number: 20110015341
    Abstract: A phenol-formaldehyde resin, which can be obtained by alkalinically catalyzed condensation of phenol and formaldehyde in the presence of at least one salt of inorganic acids and by neutralization by means of an inorganic or organic acid following the condensation, wherein the production takes place with the addition of at least one compound of the formula R1—(CH2)n—R2, in which R1 and R2, independently of one another, stand for —C(O)R, —COOR, —CN, or —NO2, and R represents H or CH3, and n has the value of 1 or 2. Also disclosed are the production of such resins and their use as binders for mineral-fiber-based insulating products.
    Type: Application
    Filed: January 21, 2008
    Publication date: January 20, 2011
    Applicant: Dynea Oy
    Inventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
  • Publication number: 20080221294
    Abstract: Resol beads are disclosed prepared by reaction of a phenol with an aldehyde, with a base as catalyst, in the presence of a colloidal stabilizer, and optionally a surfactant. The resol beads have a variety of uses, and may be thermally treated and carbonized to obtain activated carbon beads.
    Type: Application
    Filed: April 9, 2008
    Publication date: September 11, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Chester Wayne Sink, Charles Edwan Sumner, Ramesh Chand Munjal, Ruairi Seosamh O'Meadhra, Jerry Steven Fauver, Robert Melvin Schisla, Shriram Bagrodia, Tera Jill Hardin
  • Patent number: 7049387
    Abstract: The cure rate of phenol-aldehyde resins is accelerated by conjoint use of a cyclic carbonate cure accelerant and an amine cure accelerant. The cure rate is accelerated still further by addition of a resorcinol source to resin comprising a cyclic carbonate and an amine cure accelerator. Also, cured resins made in accordance with the method.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: May 23, 2006
    Assignee: Georgia-Pacific Resins, Inc.
    Inventor: Frederick C. Dupre, Jr.
  • Publication number: 20040068083
    Abstract: Phenolic resins and processes of making these phenolic resins that are useful for making binders for mineral wool insulation products are disclosed. The addition of a boron salt early in the process of making these phenolic resins leads to enhanced properties such as a reduction in the amount of tetradimers and an improvement in the stability of both the base resin and the pre-react.
    Type: Application
    Filed: October 7, 2002
    Publication date: April 8, 2004
    Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
  • Patent number: 6541576
    Abstract: A catalyst curing system or hardener for resorcinolic resins, such as resorcinol-formaldehyde or phenol-resorcinol-formaldehyde resins including methylolurea. The methylolurea may be used in combination with oxazolidine in ratios ranging from 5:95 to 95:, by molar basis. The hardener crosslinks the resins which permits reduction or “fuming” of formaldehyde as well as control of gel times of the resulting adhesive. The hardener of the present invention if of particular utility in adhesives for use in the forest products industry.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: April 1, 2003
    Assignee: Borden Chemical, Inc.
    Inventors: Earl K. Phillips, Arthur J. Garwood, William D. Detlefsen
  • Patent number: 6482946
    Abstract: A high char yield polybenzoxazine is formed by mixing (i) a benzoxazine compound, (ii) a furan compound, (iii) a benzoxazine-furan compound or combinations thereof, wherein the mixture has a benzoxazine ring to furan ring ratio from about 0.001 to about 10 and then heating the mixture for a sufficient time to form the polybenzoxazine.
    Type: Grant
    Filed: November 3, 2000
    Date of Patent: November 19, 2002
    Assignee: Dow Global Technologies Inc.
    Inventors: Marvin L. Dettloff, Jerry E. White, Marty J. Null
  • Patent number: 6160079
    Abstract: Arylamines with electron donating groups such as alkyl and alkoxy groups in the meta position on the aromatic ring change the polymerization temperature of the benzoxazine prepared therefrom and offer an opportunity for an additional crosslinking site (the para position on the aromatic amine can couple to a Mannich base generated by the opening of the oxazine ring of the benzoxazine or a methylene bridge generated by a degradation reaction). Naphthenic amines with an alkyl or alkoxy substituent on the 5.sup.th through the 8.sup.th carbon atom on the naphthalene ring can function similarly. The polymers for benzoxazines prepared from at least 10% substituted aromatic or naphthenic amines are useful due to low polymerization temperatures and higher Tg (glass transition temperature).
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: December 12, 2000
    Assignee: Edison Polymer Innovation Corporation
    Inventors: Hatsuo Ishida, Daniel Sanders
  • Patent number: 6005064
    Abstract: A novel thermosetting compound which is speedily curable, generates no by-products during curing and gives cured products having excellent heat resistance and inflammability.A thermosetting compound characterized in containing, per molecule, at least one structural unit represented by the formula (A) and at least one structural unit represented by the formula (B) in a (A)/(B) molar ratio of 1/0.25 to 1/9, said structural units being bonded directly or via at least one organic group with one another; ##STR1## wherein R.sup.1 is a methyl group, a cyclohexyl group, a nonsubstituted phenyl group or a phenyl group substituted with at least one substituent, and each hydrogen atom on the aromatic rings of (A) and (B), except for one of hydrogen atoms on ortho-positions of the hydroxy group in the aromatic ring of (A), may optionally be replaced with a substituent.
    Type: Grant
    Filed: July 6, 1998
    Date of Patent: December 21, 1999
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Yasuyuki Hirai, Teruki Aizawa, Yukio Yoshimura
  • Patent number: 5944938
    Abstract: The invention is a method of gluing wood using a reactive two component thermosetting adhesive such as a phenol-resorcinol-formaldehyde (PRF) condensation product. One component is first coated on one of the members to be bonded. The second component is then spread directly on top of the first in a manner to minimize mixing; e.g., by spraying. When the mating member to be bonded is placed against the adhesive coated first member and pressure is applied the components are mixed. This begins the curing reaction between the components so that a thermosetting adhesive bond is formed. With selected adhesives very rapid curing times are possible. A preferred adhesive has a first component comprising a PRF resin mixed with a methylene group donor hardener such as paraformaldehyde. The second part is also a PRF resin. No hardener is present in the second part. Instead an oxygen and nitrogen containing heterocycle is used as an accelerator. Morpholine is a preferred compound.
    Type: Grant
    Filed: December 17, 1996
    Date of Patent: August 31, 1999
    Assignee: Weyerhaeuser Company
    Inventors: Jack G. Winterowd, Gerald N. MacPherson
  • Patent number: 5907026
    Abstract: Weatherable polycarbonate compositions (formulations or blends) comprise polycarbonate, cycloaliphatic polyester resins, at least one of a benzotriazole, benzophenone, and triazine based UVA, and a catalyst quencher. The incorporation of the cycloaliphatic polyester resin and the benzotriazole, benzophenone, and triazine based UVA exhibits a synergistic effect, thereby resulting in unexpected enhanced protection of the polycarbonate compositions by imparting photostability to the polycarbonate formulations, thereby reducing yellowing or other forms of light induced degradation.
    Type: Grant
    Filed: August 27, 1997
    Date of Patent: May 25, 1999
    Assignee: General Electric Company
    Inventors: Arnold Factor, Randall Lee Carter, Robert Russell Gallucci
  • Patent number: 5886134
    Abstract: 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: Grant
    Filed: October 6, 1997
    Date of Patent: March 23, 1999
    Assignee: National Science Council of Republic of China
    Inventors: Chun-Shan Wang, Haan-Jang Hwang
  • Patent number: 5859169
    Abstract: Urethane-modified novolaks which are prepared by simultaneous reaction of a monohydric or polyhydric phenol (A) with an oxo compound (aldehyde or ketone) (B) and a urethane (C) in the presence of an acidic catalyst (D) at an elevated temperature of 60.degree. to 200.degree. C. and contain no interfering amounts of free starting phenol, and their use as adhesion improvers in rubbers, in particular rubbers containing reinforcing media such as steel cord or textile fibers.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: January 12, 1999
    Assignee: Vianora Resins GmbH
    Inventors: Thomas Burkhart, Siegfried Wallenwein, Gerhard Brindoepke, Gerd Walz
  • Patent number: 5847190
    Abstract: The present invention relates to dendritic, nitrogen-containing organic compounds containing at least 4 planar-chiral or axial-chiral groups, where these planar-chiral or axial-chiral groups are linked as Schiff's bases to the primary amino groups of compounds of the formula (I)(R.sup.1 R.sup.1)N--X--N(R.sup.1 R.sup.1) (I)whereR.sup.1 is (R.sup.2 R.sup.2)N--(CH.sub.2).sub.2 -- or (R.sup.2 R.sup.2)N--(CH.sub.2).sub.3 --,R.sup.2 is hydrogen or (R.sup.3 R.sup.3)N--CH.sub.2).sub.2 -- or (R.sup.3 R.sup.3)N--(CH.sub.2).sub.3 --,R.sup.3 is hydrogen or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.2 -- or (R.sup.4 R.sup.4)N--(CH.sub.2).sub.3 --,R.sup.4 is hydrogen or (R.sup.5 R.sup.5)--N--(CH.sub.2).sub.2 -- or (R.sup.5 R.sup.5)N--(CH.sub.2).sub.3 --,R.sup.5 is hydrogen or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.2 -- or (R.sup.6 R.sup.6)N--(CH.sub.2).sub.3 -- andR.sup.6 is hydrogen,X is an aliphatic and/or aromatic group, which may contain heteroatoms,which are suitable as catalysts for asymmetrical homogeneous catalysis.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
  • Patent number: 5763559
    Abstract: A guanidine-modified phenol-formaldehyde resole resin by reacting formaldehyde and phenol at a formaldehyde to phenol mole ratio above about 1.5:1 in the presence of an effective amount of an alkaline catalyst and in the presence of a catalytic amount of a guanidine salt. The resin is suitable for use in adhesives for high moisture content substrates.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: June 9, 1998
    Assignee: Georgia-Pacific Resins, Inc.
    Inventor: Eric Peter Black
  • Patent number: 5763558
    Abstract: A process for hardening a composition and a hardenable composition, in wh there are used:at least one novolac resin;at least one hardener of the resin, selected from the group consisting of substituted melamines;at least one compound comprising at least one ##STR1## group, this compound being without methylol group and ether group corresponding to methylol, and/or at least one reagent capable of giving such a compound under the conditions of the hardening.The hardening of the resin is caused by the action of heat.
    Type: Grant
    Filed: June 11, 1996
    Date of Patent: June 9, 1998
    Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & Cie
    Inventors: Brigitte Marie Chauvin, Olivier Durel
  • Patent number: 5688893
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: November 18, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • Patent number: 5614349
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: March 25, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • Patent number: 5538761
    Abstract: Emissions of formaldehyde and ammonia from urea-extended alkaline phenol/formaldehyde resole fiberglass binders are sharply reduced by using as a catalyst an emission-reducing effective amount of an acidifying agent which is a hydrolyzable inorganic salt, mineral acid, monomeric carboxylic acid or partial ester of a polycarboxylic acid such that the instantaneous pH of the binder solution is lower than 5.5. Use of the catalysts of the subject process also allow for additional urea-extension without degradation of fiberglass product physical properties. The preferred catalyst is aluminum sulfate in an amount of from 2.0 weight percent to about 4.0 weight percent based on the resin solids.
    Type: Grant
    Filed: June 13, 1995
    Date of Patent: July 23, 1996
    Assignee: Schuller International, Inc.
    Inventor: Thomas J. Taylor
  • 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: 5476750
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions and a substantially consistent molecular weight. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: December 19, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
  • 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: 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: 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: 5093385
    Abstract: The invention relates to an accelerated photoiniferter polymerization method which involves the addition of a polymerization accelerating amount of a at least one metal compound accelerator during the photoiniferter polymerization process.Preferably, the metal compound or compounds used are represented by the general formula M.sub.x L.sub.z whereinM is a cation having a valency of z of a metal which is selected from the group consisting of tin, zinc, cobalt, titanium, palladium, and lead;x is an integer of at least 1;L is an anion having a valency of x which is selected from the group consisting of C.sub.1-20 alkyl, -aryl, --OR, ##STR1## NO.sub.3.sup.--, SO.sub.4.sup..dbd., and PO.sub.4.sup.-3 ; R is selected from the group consisting C.sub.1-20 alkyl and aryl; andz is an integer of at least 1.Most preferably, the metal compound is selected from the group consisting of stannous 2-ethylhexanoate, zinc 2-ethylhexanoate and mixtures thereof.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: March 3, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Mahfuza B. Ali
  • 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: 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: 4942217
    Abstract: A heat-hardenable binder comprising (a) a phenolic resin of a phenolic compound and formaldehyde in a molar ratio of 1:1 to 1:2 and (b) an effective amount of a hardener mixture of hexamethylenetetramine and an acidic latent hardening agent with reduced emission problems and curing rapidly.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 17, 1990
    Assignee: Rutgerswerke AG
    Inventors: Arno Gardziella, Alois Kwasniok
  • Patent number: 4940852
    Abstract: A liquid or viscous curable adhesive composition having a prolonged pot life which is composed of a liquid or viscous curable resin which has, preferably evenly and randomly dispersed therethroughout, a multiplicity of rupturable microcapsules containing a curing agent in an amount sufficient to cure the resin. The microcapsules are rupturable upon the application thereto of external pressure, or other mechanical manipulation. Upon rupture, the curing agent is released into coacting relationship with the curable resin and forms therewith an activated adhesive composition.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: July 10, 1990
    Assignee: Milton P. Chernack
    Inventor: Milton Chernack
  • Patent number: 4904753
    Abstract: Disclosed is a catalyst system which improves the cure time of acid-catalyzable resole resins while providing extended shelf life thereof. Broadly, the present invention includes a method for formulating an acid-catalyzed, non-aqueous resole resin composition and to the composition itself. The catalyst system comprises an acid catalyst and an oxidizing agent in an amount adequate for cure in at least about the same time that occurs by use of at least twice the amount of said acid catalyst alone. The shelf life of the catalyzed resole resin is greater with the inventive catalyst system than with an equivalent resole resin containing only the acid catalyst in twice the amount.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: February 27, 1990
    Assignee: Ashland Oil, Inc.
    Inventors: Golden F. Watts, Warren L. Robbins
  • Patent number: 4870154
    Abstract: A method of producing a novolac phenolic resin having quick-curing properties and good fluidity is disclosed, whereby the novolac resin is prepared by reacting a phenol with an aldehyde using an acidic catalyst and thereafter adding an ammonium halide. The ammonium halide is added in amounts of about 0.05 to 3 wt % of the solid resin, and the conversion of aldehyde is not less than 90% and the water content of the resin is not less than 5%.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: September 26, 1989
    Assignee: Sumitomo Durez Company, Ltd.
    Inventors: Yukio Saeki, Toshiaki Nishimura, Kozuichi Ikeda
  • Patent number: 4851279
    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 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: Grant
    Filed: December 21, 1987
    Date of Patent: July 25, 1989
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4831086
    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 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: Grant
    Filed: October 5, 1987
    Date of Patent: May 16, 1989
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 4808639
    Abstract: A liquid or viscous curable adhesive composition having a prolonged pot life which is composed of a liquid or viscous curable resin which has, preferably evenly and randomly dispersed therethroughout, a multiplicity of rupturable microcapsules containing a curing agent in an amount sufficient to cure the resin. The microcapsules are rupturable upon the application thereto of external pressure, or other mechanical manipulation. Upon rupture, the curing agent is released into coacting relationship with the curable resin and forms therewith an activated adhesive composition.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: February 28, 1989
    Assignee: Production Previews, Inc.
    Inventor: Milton Chernack
  • Patent number: 4656239
    Abstract: The process described herein involves the gradual addition of aqueous formaldehyde, containing 35-60 percent by weight of formaldehyde, to a phenol maintained at a temperature of 60.degree.-100.degree. C., preferably 70.degree.-90.degree. C., and at a reduced pressure of 11-26 inches of mercury in the presence of an alkaline catalyst. The rate of formaldehyde addition is such that the exothermic reaction aids in maintaining the stated temperature range and thereby simultaneously distills approximately all the water added with the formaldehyde and that formed by the condensation so that the volume of the reaction mass is maintained approximately constant. This constant volume allows efficient use of the equipment.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 7, 1987
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Bohumir Lepeska
  • Patent number: 4640971
    Abstract: A resole resin in the form of microspherical particles whose surfaces are partly or entirely covered with a coating of a substantially water-insoluble inorganic salt and which are not larger than 500 .mu.m in size, and a process for producing such resole resin. The resole resin comprises solid particles that are highly heat reactive and can be stored in a stable manner for a prolonged period. The resin particles can be used with good results in all fields of applications (e.g., moldings, laminations and binders) where conventional phenolic resins are used.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: February 3, 1987
    Assignee: Unitika Ltd.
    Inventors: Yoshiaki Echigo, Mutsunori Yamao, Yoshiyuki Suematu, Tadashi Ishikura, Keiichi Asami, Ritsuko Shidei
  • Patent number: 4612254
    Abstract: Novel metal-modified phenolic resins useful in the color developer part of a carbonless copy paper system are disclosed, as well as methods for preparing such resins. The metal-modified phenolic resins are reaction products of an aromatic carboxylic acid and a partial condensation reaction product (an oligomer) of a phenol and an aldehyde. The metal-containing compound is added either to the mixture of phenol and aldehyde in forming the oligomer or to the mixture of aromatic carboxylic acid and the oligomer. The color developer materials of the invention are coated on a paper substrate which forms a part of a pressure sensitive recording paper system. The color developer materials exhibit improved performance over prior art colored developer materials.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: September 16, 1986
    Assignee: Occidental Chemical Corporation
    Inventors: James W. Ginter, Donald H. Thorpe, Victor F. G. Cooke
  • Patent number: 4579876
    Abstract: A polyol comprising an alkoxylated modified resole, said modified resole being formed by the reaction of(i) a phenolic compound and/or mixtures of homologues thereof,(ii) urea and/or melamine,(iii) an organic primary and/or secondary amine group-containing compound, and(iv) an aldehyde.
    Type: Grant
    Filed: January 10, 1985
    Date of Patent: April 1, 1986
    Assignee: Mobay Chemical Corporation
    Inventor: Miltiadis I. Iliopulos
  • Patent number: 4454298
    Abstract: A granular or powdery resin which is a condensation product of a phenol and an aldehyde and optionally a nitrogen-containing compound having at least two active hydrogens, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of said particles having a particle diameter of 0.1 to 150 microns,(B) having such a size that at least 50% by weight thereof can pass through a 100 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 500 ppm, and(D) having a methanol solubility (S) of more than 20% by weight when about 10 g of the resin is heated under reflux in 500 ml of substantially anhydrous methanol.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: June 12, 1984
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4414379
    Abstract: A granular or powdery nitrogen-containing phenol-aldehyde copolymer resin which is a condensation product of a phenol, a nitrogen-containing compound having at least two active hydrogen atoms and an aldehyde, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of said particles having a particle diameter of 0.1 to 100 microns,(B) having such a size that at least 50% by weight thereof can pass through a 150 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm, and(D) having a D.sub.960-1020 /D.sub.1450-1500 ratio of from 0.1 to 2.0 in its infrared absorption spectrum.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: November 8, 1983
    Assignees: Kanebo Ltd., Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4414378
    Abstract: A granular or powdery resin which is a condensation product of a phenol and formaldehyde, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of the particles having a particle diameter of 0.1 to 150 microns,(B) having such a size that at least 50% by weight thereof can pass through a 100 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm,(D) having a D.sub.990-1015 /D.sub.1600 ratio of from 0.2 to 9.0 and a D.sub.890 /D.sub.1600 ratio of from 0.09 to 1.0 in its infrared absorption spectrum measured by a KBr tablet method, wherein D.sub.1600 represents the absorption intensity of an absorption peak at 1600 cm.sup.-1, D.sub.990-1015 represents the highest absorption intensity of absorption peaks at 990 to 1015 cm.sup.-1, and the D.sub.890 represents the absorption intensity of an absorption peak at 890 cm.sup.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: November 8, 1983
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4404358
    Abstract: The invention relates to oil-modified resole varnishes particularly useful for impregnating paper laminates. Specifically, the invention relates to such compositions in which linseed oil or mixtures thereof with tung oil or oiticica oil is used as the modifier for the resole. Laminates prepared using the varnish are characterized by manufacturing economy, enhanced punchability and other salutary properties.
    Type: Grant
    Filed: October 30, 1980
    Date of Patent: September 13, 1983
    Assignee: General Electric Company
    Inventor: Bruce Q. Ballert