Nitrogen-containing Material Contains A Nitrogen Atom Directly Bonded To A Carbon Atom Patents (Class 528/146)
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Patent number: 10280359Abstract: 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: GrantFiled: December 27, 2017Date of Patent: May 7, 2019Assignee: Baker Hughes IncorporatedInventors: Anil K. Sadana, Jeffrey R. Potts
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Patent number: 9040650Abstract: 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: GrantFiled: November 19, 2010Date of Patent: May 26, 2015Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES, ECOLE NATIONALE SUPERIEURE DE CHIMIE DE MONTPELLIERInventors: Sylvain Caillol, Bernard Boutevin, Ghislain David, Carine Burguiere
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Patent number: 8791214Abstract: 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: GrantFiled: May 25, 2012Date of Patent: July 29, 2014Assignee: DIC CorporationInventors: Kan Takeuchi, Etsuko Suzuki, Kunihiro Morinaga, Kazuo Arita
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Publication number: 20120277396Abstract: 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: ApplicationFiled: November 19, 2010Publication date: November 1, 2012Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), ECOLE NATIONALE SUPERIEURE DE CHIMMIE DE MONTPELLIER, UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUESInventors: Sylvain Caillol, Bernard Boutevin, Ghislain David, Carine Burguiere
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Publication number: 20120271028Abstract: 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: ApplicationFiled: July 3, 2012Publication date: October 25, 2012Applicant: EASTMAN CHEMICAL COMPANYInventors: 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
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Patent number: 8017562Abstract: 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: GrantFiled: November 5, 2010Date of Patent: September 13, 2011Assignee: Brine-Add Fluids Ltd.Inventors: David P. Horton, Ioan Ghesner
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Publication number: 20110015341Abstract: A phenol-formaldehyde resin, which can be obtained by alkalinically catalyzed condensation of phenol and formaldehyde in the presence of at least one salt of inorganic acids and by neutralization by means of an inorganic or organic acid following the condensation, wherein the production takes place with the addition of at least one compound of the formula R1—(CH2)n—R2, in which R1 and R2, independently of one another, stand for —C(O)R, —COOR, —CN, or —NO2, and R represents H or CH3, and n has the value of 1 or 2. Also disclosed are the production of such resins and their use as binders for mineral-fiber-based insulating products.Type: ApplicationFiled: January 21, 2008Publication date: January 20, 2011Applicant: Dynea OyInventors: Stefan Kowatsch, Karl Loidolt, Christoph Prock
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Publication number: 20080221294Abstract: 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: ApplicationFiled: April 9, 2008Publication date: September 11, 2008Applicant: EASTMAN CHEMICAL COMPANYInventors: Chester Wayne Sink, Charles Edwan Sumner, Ramesh Chand Munjal, Ruairi Seosamh O'Meadhra, Jerry Steven Fauver, Robert Melvin Schisla, Shriram Bagrodia, Tera Jill Hardin
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Patent number: 7049387Abstract: 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: GrantFiled: October 16, 2001Date of Patent: May 23, 2006Assignee: Georgia-Pacific Resins, Inc.Inventor: Frederick C. Dupre, Jr.
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Publication number: 20040068083Abstract: 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: ApplicationFiled: October 7, 2002Publication date: April 8, 2004Inventors: Kwok Tang, Ruben A. Santos, Bohumila Zapletal
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Patent number: 6541576Abstract: 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: GrantFiled: August 11, 1998Date of Patent: April 1, 2003Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, Arthur J. Garwood, William D. Detlefsen
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Patent number: 6482946Abstract: 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: GrantFiled: November 3, 2000Date of Patent: November 19, 2002Assignee: Dow Global Technologies Inc.Inventors: Marvin L. Dettloff, Jerry E. White, Marty J. Null
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Patent number: 6160079Abstract: 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: GrantFiled: April 14, 1999Date of Patent: December 12, 2000Assignee: Edison Polymer Innovation CorporationInventors: Hatsuo Ishida, Daniel Sanders
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Patent number: 6005064Abstract: 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: GrantFiled: July 6, 1998Date of Patent: December 21, 1999Assignee: Hitachi Chemical Company, Ltd.Inventors: Yasuyuki Hirai, Teruki Aizawa, Yukio Yoshimura
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Patent number: 5944938Abstract: 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: GrantFiled: December 17, 1996Date of Patent: August 31, 1999Assignee: Weyerhaeuser CompanyInventors: Jack G. Winterowd, Gerald N. MacPherson
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Patent number: 5907026Abstract: 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: GrantFiled: August 27, 1997Date of Patent: May 25, 1999Assignee: General Electric CompanyInventors: Arnold Factor, Randall Lee Carter, Robert Russell Gallucci
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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: 5859169Abstract: 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: GrantFiled: September 8, 1997Date of Patent: January 12, 1999Assignee: Vianora Resins GmbHInventors: Thomas Burkhart, Siegfried Wallenwein, Gerhard Brindoepke, Gerd Walz
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Patent number: 5847190Abstract: 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: GrantFiled: May 20, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Wolfgang Paulus, Fritz Vogtle, Jorg Issberner
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Patent number: 5763559Abstract: 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: GrantFiled: January 21, 1997Date of Patent: June 9, 1998Assignee: Georgia-Pacific Resins, Inc.Inventor: Eric Peter Black
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Patent number: 5763558Abstract: 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: GrantFiled: June 11, 1996Date of Patent: June 9, 1998Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & CieInventors: Brigitte Marie Chauvin, Olivier Durel
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Patent number: 5688893Abstract: 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: GrantFiled: December 20, 1996Date of Patent: November 18, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
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Patent number: 5614349Abstract: 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: GrantFiled: December 29, 1992Date of Patent: March 25, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
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Patent number: 5538761Abstract: 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: GrantFiled: June 13, 1995Date of Patent: July 23, 1996Assignee: Schuller International, Inc.Inventor: Thomas J. Taylor
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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: 5476750Abstract: 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: GrantFiled: December 29, 1992Date of Patent: December 19, 1995Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
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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: 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: 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: 5093385Abstract: 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: GrantFiled: December 21, 1989Date of Patent: March 3, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventor: Mahfuza B. Ali
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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: 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: 4942217Abstract: 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: GrantFiled: October 26, 1988Date of Patent: July 17, 1990Assignee: Rutgerswerke AGInventors: Arno Gardziella, Alois Kwasniok
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Patent number: 4940852Abstract: 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: GrantFiled: November 14, 1988Date of Patent: July 10, 1990Assignee: Milton P. ChernackInventor: Milton Chernack
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Patent number: 4904753Abstract: 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: GrantFiled: March 23, 1988Date of Patent: February 27, 1990Assignee: Ashland Oil, Inc.Inventors: Golden F. Watts, Warren L. Robbins
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Patent number: 4870154Abstract: 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: GrantFiled: November 20, 1987Date of Patent: September 26, 1989Assignee: Sumitomo Durez Company, Ltd.Inventors: Yukio Saeki, Toshiaki Nishimura, Kozuichi Ikeda
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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: 4808639Abstract: 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: GrantFiled: July 22, 1987Date of Patent: February 28, 1989Assignee: Production Previews, Inc.Inventor: Milton Chernack
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Patent number: 4656239Abstract: 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: GrantFiled: March 27, 1986Date of Patent: April 7, 1987Assignee: Plastics Engineering CompanyInventors: Phillip A. Waitkus, Bohumir Lepeska
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Patent number: 4640971Abstract: 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: GrantFiled: July 17, 1985Date of Patent: February 3, 1987Assignee: Unitika Ltd.Inventors: Yoshiaki Echigo, Mutsunori Yamao, Yoshiyuki Suematu, Tadashi Ishikura, Keiichi Asami, Ritsuko Shidei
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Patent number: 4612254Abstract: 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: GrantFiled: March 7, 1985Date of Patent: September 16, 1986Assignee: Occidental Chemical CorporationInventors: James W. Ginter, Donald H. Thorpe, Victor F. G. Cooke
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Patent number: 4579876Abstract: 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: GrantFiled: January 10, 1985Date of Patent: April 1, 1986Assignee: Mobay Chemical CorporationInventor: Miltiadis I. Iliopulos
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Patent number: 4454298Abstract: 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: GrantFiled: December 23, 1982Date of Patent: June 12, 1984Assignee: Kanebo Ltd.Inventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4414379Abstract: 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: GrantFiled: June 16, 1982Date of Patent: November 8, 1983Assignees: Kanebo Ltd., Mitsubishi Chemical Industries LimitedInventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4414378Abstract: 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: GrantFiled: April 15, 1982Date of Patent: November 8, 1983Assignee: Mitsubishi Chemical Industries LimitedInventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4404358Abstract: 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: GrantFiled: October 30, 1980Date of Patent: September 13, 1983Assignee: General Electric CompanyInventor: Bruce Q. Ballert