Material Contains A Group Ia Metal Atom (li, Na, K, Rb, Cs, Fr) Patents (Class 528/147)
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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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Patent number: 8742056Abstract: Disclosed is a solid resol-type phenolic resin having: methylol groups and dimethylene ether bonds, as functional groups bound to phenolic nuclei; a content of methylol group, per 1 mol of the phenolic nuclei, of 0.8 mol or more and 1.3 mol or less; a content of dimethylene ether bond, per 1 mol of the phenolic nuclei, of 0.1 mol or less; a weight-average molecular weight of a tetrahydrofuran-soluble fraction, measured by gel permeation chromatography (GPC), of 800 or larger and 4,000 or smaller; and a content of mononuclear phenolic compound of 10% by weight or less.Type: GrantFiled: March 14, 2011Date of Patent: June 3, 2014Assignee: Sumitomo Bakelite Co., Ltd.Inventors: Yuji Suzuki, Kazuya Kitagawa
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Patent number: 8487025Abstract: The present invention relates to an aromatic branched polycarbonate, produced via melt transesterification of a bisphenol with a diaryl carbonate in the presence of a branching agent, wherein the aromatic branched polycarbonate comprises branching point structures and structures of formula (D) wherein X is a single bond, C1- to C6-alkylene, C2- to C5-alkylidene or C5- to C6-cycloalkylidene, optionally substituted by C1- to C6-alkyl; wherein the amount of D in the aromatic branched polycarbonate is in the range of from 5 to 450 mg per kg of the aromatic branched polycarbonate; and wherein the ratio of the total branching point structures to the total structures of the formula D in the aromatic branched polycarbonate is in the range of from 8 to 200.Type: GrantFiled: April 7, 2011Date of Patent: July 16, 2013Assignee: Bayer Material Science AGInventors: Stephan Konrad, Helmut-Werner Heuer, Karl-Heinz Köhler, Christian Münnich, Rolf Wehrmann
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Publication number: 20120263522Abstract: A dowel coated with a heat-activated, B-staged formaldehyde-based resin and a related method of using the resin-coated dowel for joining separate components together.Type: ApplicationFiled: March 23, 2012Publication date: October 18, 2012Applicant: GEORGIA-PACIFIC CHEMICALS LLCInventors: Robert A. Breyer, Bobby L. Williamson, Steven O. Clausen, Daniel Tingley
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Patent number: 7662902Abstract: A phenolic resin having not more than 5 wt% of free bisphenol and a molecular weight distribution Mw/Mn of not more than 2.0 is prepared by reacting a bisphenol and aldehyde in the presence of an alkaline catalyst at a temperature of from 0° C. to 100° C., neutralizing with an acid, adding an acid to adjust the pH to from 0 to 6, heating to a temperature of from 50° C. to 200° C, and vacuuming to recover the phenolic resin.Type: GrantFiled: November 9, 2006Date of Patent: February 16, 2010Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen Yuan Hwang, An Pang Tu, Chun Hsiung Kao, Fang Shian Su
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Patent number: 6432254Abstract: A method for making a consolidated wood product comprising coating wood components with a B-stageable, phenol-formaldehyde resole resin; heating the coated wood components to about 80 to 140° C. for a time sufficient to advance the resin to a B-stage; forming a mat or stack of the wood components coated with the B-stage resin; exposing the mat or stack of coated wood components to a saturated or superheated steam atmosphere in a hot press; and compressing the layup to form the consolidated wood product. The phenol-formaldehyde resole resin used in the method has a number average molecular weight of between about 200 and 600, has a F:P mole ratio of about 1.3:1 to 2.0:1, and has been modified with 0 to about 5.5 wt % of caustic based on resin solids.Type: GrantFiled: November 26, 1997Date of Patent: August 13, 2002Assignee: Georgia-Pacific Resins Inc.Inventors: Eric P. Black, Michael E. Hittmeier, W. Hayes Ingram, R. Scott Johnson
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Patent number: 6307009Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.Type: GrantFiled: December 29, 1999Date of Patent: October 23, 2001Assignee: Owens Corning Fiberglas Technology, Inc.Inventor: Jianjun Li
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Publication number: 20010029291Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.Type: ApplicationFiled: December 29, 1999Publication date: October 11, 2001Inventor: JIANJUN LI
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Patent number: 6291600Abstract: In a novel method of homo- or copolymerization of vinyl chloride, a specified coating agent is applied on the surfaces of the portions which will become into contact with the vinyl chloride monomer during the polymerization process. The coating agent is in a form of an aqueous solution of a modified condensation product of phenol and aldehyde, the pH of the solution being adjusted in a range that the product is dissolved at an ambient temperature upon coating of the solution and separates out of the solution upon being heated on the surfaces. The wall surface of the polymerization tank and the like is then coated with a thin film of the coating agent having a uniform thickness and being strongly adhered to the wall surface, thereby providing an excellent effect of preventing adhesion of the product polymer to the wall surface.Type: GrantFiled: April 9, 1993Date of Patent: September 18, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Seiichi Masuko, Ichisaburo Nakamura, Yoshimatsu Naka, Keiichi Fukuda, Akira Yamamoto, Yasuyuki Hatakeyama, Akihiro Yamaguchi, Keizaburo Yamaguchi
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Patent number: 6245882Abstract: Method for the manufacture of a phenolic resin emulsion and/or dispersion, wherein an aldehyde, a phenolic compound and an alkaline catalyst are allowed to react at a temperature of 40-100° C. until a desired degree of condensation is achieved, and the pH of the resin is adjusted to a value below 9 using an acid in the presence of a surface active agent or a mixture thereof at a temperature below 100° C. and a phenolic resin emulsion and/or dispersion is obtained providing a colorless or light-colored glue line or surface when cured.Type: GrantFiled: September 1, 1999Date of Patent: June 12, 2001Assignee: Neste Chemicals OyInventors: Leena Matilainen, Guomin Bian, Claude Ostiguy, Rick Cheng, Matti Satuli, Kari Leskinen, Kwok Tang
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Patent number: 6232427Abstract: Methods of making halogenated aromatic esters are described. Polymer compositions including halogenated aromatic esters are also described. In one embodiment, the method includes contacting a tetrabromophthalate, an alcohol and barium acetate.Type: GrantFiled: December 22, 1999Date of Patent: May 15, 2001Assignee: Teknor Apex CompanyInventors: John A. Buono, Maryellen Cobb, Tao T. Tao
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Patent number: 6214964Abstract: A process for forming a phenol formaldehyde resin, the process comprising the steps of: (i) reacting phenol with an excess of a formaldehyde material in the presence of an acid or base catalyst until water separates from the reactants as an immiscible layer; (ii) adding a mixture comprising an excess of polyhydric alcohol and an aromatic dicarboxylic or tricarboxylic acid, salt or anhydride thereof to the phenol and formaldehyde reaction mixture followed by addition of an alpha hydroxy acid; (iii) adding a non-aqueous solvent, wherein at least some of said water is removed either before addition of the mixture preparated in step (ii) or after addition of the alpha hydroxy acid; (iv) preparing a solution comprising a Lewis acid, a polyhydric alcohol, an alpha hydroxy acid, a non-aqueous solvent, an aromatic sulphonic acid and sulphuric or hydrochloric acid; (v) adding the solution formed in step (iv) to the mixture formed in step (ii) and allowing the mixture to cure.Type: GrantFiled: February 18, 2000Date of Patent: April 10, 2001Inventor: Barry William Ryan
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Patent number: 6046252Abstract: A binder composition of a phenolic novolac resin and a (lower) alkoxylated triazine-formaldehyde resin curing agent is disclosed. The triazine resins have sufficient carbon atoms in the alkoxy groups so as to provide a curing agent having a water solubility of less than 15%. The binder cures at high temperatures so as to provide improved flow and prolonged workability to the composition. The compositions are useful in refractory applications having a need for high temperature curing agents such as for maintenance and repair within refractory vessels by gunning/spraying, manufacture of electrodes by the Soderberg method, and for use in blast furnace tap holes.Type: GrantFiled: February 25, 1997Date of Patent: April 4, 2000Assignee: Borden Chemical, Inc.Inventor: Arthur H. Gerber
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Patent number: 5847058Abstract: A process for the production of a storage-stable, modified phenol-aldehyde resol resin includes the use of an alkylresorcinol modifier and preferably a readily-available mixture of alkylresorcinols. A binder system includes the modified phenol-aldehyde resin combined with a curing agent that includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The resin and binder system are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).Type: GrantFiled: April 5, 1996Date of Patent: December 8, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5756599Abstract: A process for producing a phenol-aldehyde (e.g., cresol-aldehyde) resin that is modified with a dihydroxybenzene compound. The resin may form a binder system when combined with a curing agent which includes an additional source of an aldehyde. The resin and adhesive are useful in the production of wood composite articles by a steam injection process.Type: GrantFiled: July 7, 1997Date of Patent: May 26, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5686506Abstract: A binder solution of a phenolic novolak resin in solvent, preferably furfuryl alcohol containing at least one chemical agent such as amines containing one to five, preferably two to four, nitrogen atoms, glycerine or mixtures thereof. Preferably, the binder solution contains about 0.2 to about 1.5 weight percent water. The binder solution is for binding refractory objects, preferably those containing doloma (calcined dolomite) aggregate. Methods of mixing these ingredients and using the mixture are also disclosed. Bricks made from the doloma aggregate mixed with the binder solution show good ambient temperature green strength and enhanced modulus of rupture after curing and coking.Type: GrantFiled: April 4, 1995Date of Patent: November 11, 1997Assignee: Borden Chemical, Inc.Inventor: Arthur Harry Gerber
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Patent number: 5684114Abstract: A two-part adhesive is provided wherein the first part comprises a stable aqueous alkaline monohydroxylic phenolic resole resin solution containing a methylene donor such as oxazolidine or a methylolurea and the second part comprises a stable resorcinolic resin precondensate having a shortage of formaldehyde and optionally containing a catalyst such as an ester functional compound for the resole resin. The resin in each part exhibits viscosity stability of an unmodified resin until mixed with the other part wherein the methylene donor, of the first part catalyzes the resorcinolic resin of the second part and the catalyst, when used, of the second part catalyzes the monohydroxylic phenolic resole resin of the first part. The adhesive finds utility in the production of structural lignocellulosic panels.Type: GrantFiled: June 7, 1995Date of Patent: November 4, 1997Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
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Patent number: 5684115Abstract: A processes for producing a (co)polycarbonate having a low terminal hydroxyl group concentration and being excellent in heat resistance and hue, which comprises melt-polycondensing a dihydroxy compound with a carbonic diester in the presence of a catalyst for transesterification selected from the group consisting of a nitrogen-containing basic compound, an alkali metal borate and an alkaline earth metal borate and in the presence of a specific ester compound.Type: GrantFiled: June 1, 1995Date of Patent: November 4, 1997Assignee: Daicel Chemical Industries, Ltd.Inventors: Tatsuya Kanno, Yutaka Hukuda, Yasuhiro Oshino
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Patent number: 5681916Abstract: Urea-modified, highly reactive phenolic resins useful as center-layer bonding agents in the manufacture of particleboard are provided by condensing phenol and formaldehyde until shortly before gelation takes place such that, after addition of urea, relatively low-alkaline, urea-modified phenolic resins are obtained which my optionally be stored and to which, shortly before processing them into glues for center-layer particles, alkali is added in sufficient quantities to ensure rapid cross-linking of the phenolic resin.Type: GrantFiled: June 29, 1995Date of Patent: October 28, 1997Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Adolf Buschfeld, Matthias Lattekamp, Manfred Gramse, Hans-Jurgen Krezmin
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Patent number: 5637658Abstract: A process for the production of a modified phenol-aldehyde resin which may form a binder system when combined with a curing agent which includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The inventive phenol-aldehyde resin may be modified with compounds from one of the following classes: (1) dihydroxybenzenes, (2) arninophenols, and (3) phenylenediamines. The resin and adhesive are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).Type: GrantFiled: May 23, 1995Date of Patent: June 10, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5629083Abstract: A process for the production of modified phenol-aldehyde resins includes the use of a modifier selected from melamine, urea, and other suitable nonvolatile organic compounds. The phenolic component of the resins preferably includes a difunctional phenolic compound. The inventive resins resist precuring and are particularly useful in blowline blending procedures.Type: GrantFiled: June 7, 1995Date of Patent: May 13, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5623032Abstract: 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: GrantFiled: June 23, 1995Date of Patent: April 22, 1997Assignee: Angus Chemical CompanyInventor: Gaoming Wu
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Patent number: 5594098Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions, utilizing treated ion exchange resins. A method is also provided for producing photoresist composition having a very low level of metal ions from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: July 11, 1994Date of Patent: January 14, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5580949Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions, utilizing treated ion exchange resins. A method is also provided for producing photoresist composition having a very low level of metal ions from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: June 2, 1995Date of Patent: December 3, 1996Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5470924Abstract: A process for forming a phenol formaldehyde resin including the steps of: (i) forming a first additive including a glycol and an aromatic dicaborxylic acid; (ii) adding said first additive as well as an alpha hydroxy acid to a first resin component comprising resin precursors including phenol, formaldehyde, an acid catalyst or a base catalyst after said precursors have reacted for 40-55 minutes and/or when water has separated from said precursors; (iii) isolating or storing said first resin component which is maintained in a non cured state by the addition of said first additive; (iv) forming a second additive including zinc chloride, an alpha hydroxy acid, para toluene sulphonic acid, sulphuric or hydrochloric acid and a non aqueous solvent; (v) adding said second additive to a second resin component which includes resin precursors phenol, formaldehyde, methanol and an aliphatic dicarboxylic acid after said precursors have reacted for 20-30 minutes; (vi) combining said first resin component and said second rType: GrantFiled: November 24, 1993Date of Patent: November 28, 1995Inventor: Barry W. Ryan
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Patent number: 5451657Abstract: An aqueous phenol-formaldehyde resin solution with formaldehyde-phenol mol ratio in the range of 1.8 to 2.8, polymerization catalyst of 3% to 9% by weight, measured as NaOH equivalent, with less than 1% by weight potassium hydroxide, and about 0.1% to about 0.75% by weight potassium carbonate added after the catalytically-activated polymerization reaction has subsided while the resin is both soluble and fusible ("A" resol stage). Adhesive binders exhibit tolerance for variables in veneer moisture content from 0% to around 25% and in production timing from delivery of the veneer for assembly to curing of around 10 minutes to about 2 hours without significant degradation of bonding quality.Type: GrantFiled: June 13, 1994Date of Patent: September 19, 1995Assignee: Neste Resins CorporationInventor: Norman A. Chappelie
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Patent number: 5359024Abstract: The invention relates to a process for the preparation of a phenol-formaldehyde resin by causing phenol and formaldehyde to condense under the influence of a basic catalyst, the catalyst being an aqueous solution containing alkali metal ions, carbonate ions, ions of carboxylic acids and one or more ions chosen from the group comprising transition metal ions and borates.Type: GrantFiled: August 17, 1993Date of Patent: October 25, 1994Assignee: DSM N.V.Inventors: Renier H. M. Kierkels, van Kempen Carolien H. M., Henricus A. C. Baur
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Patent number: 5342880Abstract: An aqueous phenol-formaldehyde resin solution with formaldehyde-phenol mol ratio in the range of 1.8 to 2.8, polymerization catalyst of 3% to 9% by weight, measured as NaOH equivalent, with less than 1% by weight potassium hydroxide, and about 0.1% to about 0.75% by weight potassium carbonate added after the catalytically-activated polymerization reaction has subsided while the resin is both soluble and fusible ("A" resol stage). Adhesive binders exhibit tolerance for variables in veneer moisture content from 0% to around 25% and in production timing from delivery of the veneer for assembly to curing of around 10 minutes to about 2 hours without significant degradation of bonding quality.Type: GrantFiled: March 20, 1992Date of Patent: August 30, 1994Assignee: Neste Resins CorporationInventor: Norman A. Chappelie
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Patent number: 5260406Abstract: A stain-resist agent for polyamide fibers, its preparation and use are disclosed. The stain-resist agent is the condensation product of bis-hydroxyphenylsulfone with 0.5 to 1.0 mole of formaldehyde, per mole of bis-hydroxyphenylsulfone, and 0.15 to 1.5 moles of mercaptoacetic acid or mercaptosuccinic acid per mole of bis-hydroxyphenylsulfone and ammonium hydroxide or an alkali metal hydroxide in an amount sufficient to neutralize the mercapto acid plus an excess of about 0.2 to 0.6 mole of hydroxide per mole of bis-hydroxyphenylsulfone. Generally the reaction is carried out at 110.degree. to 180.degree. C. for 1 to 48 hours, with 130.degree. to 160.degree. C. for 3 to 24 hours being preferred. The product is applied to the polyamide fibers from an aqueous bath to provide a coating of 0.5 to 5.0 wt % stain-resist agent. The stain-resist is applied in the presence of a magnesium salt.Type: GrantFiled: April 14, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Engelbert Pechhold
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Patent number: 5254664Abstract: A reaction of the compound (A) having at least two 2-oxazoline groups with the compound (B) having at least two functional groups of one or a plural kind selected from the group consisting of an aromatic hydroxyl group, an amino group and a thiol group proceeds in a short period of time to produce a cured resin with superior mechanical strength, heat resistance and adhesion properties.Type: GrantFiled: December 31, 1991Date of Patent: October 19, 1993Assignee: Nippon Shokubai Co., Ltd.Inventors: Subhash C. Narang, Asutosh Nigam, Apparao Satyam, Susanna C. Ventura, Yoshihiro Arita
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Patent number: 5182357Abstract: One hundred percent thermosetting phenol/formaldehyde (P/F) resin and method of preparation thereof are disclosed. The resin comprises a molar ratio of F/P of about 1.2-1.7, has a softening point of about 80.degree. C. and cures at temperature of about 140.degree.-160.degree. C. The method comprises heating the reactants in a solvent-less system in the presence of an ortho directing catalyst while monitoring the amount of free formaldehyde present in the reaction system.Type: GrantFiled: October 22, 1991Date of Patent: January 26, 1993Assignee: DAP, Inc.Inventor: Gary L. Linden
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Patent number: 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: 5079332Abstract: A phenol-formaldehyde resole resin solution useful in adhesives for preparing wood laminates from a plurality of wood veneers, prepared by reacting at least an equal molar amount of formaldehyde with phenol in the presence of sodium hydroxide and a water-soluble potassium salt selected from the group consisting of potassium chloride, potassium sulfate and mixtures thereof.Type: GrantFiled: April 17, 1989Date of Patent: January 7, 1992Assignee: Georgia-Pacific Resins, Inc.Inventor: Charles Whittemore
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Patent number: 5074946Abstract: It has now been found that when there is a partial or complete replacement of the sodium hydroxide that is used to make a sodium phenolate resole resin by a molar equivalent of potassium hydroxide, a far faster curing resin is obtained. Such potassium-modified phenolic resins exhibit significant improvement in cure speed without loss of flowability. To the contrary, these resins act as though they were lower molecular weight condensation products. Reduced application rates are possible. The combination of faster cure and lower application rates has allowed such resins to be used as effective adhesives for plywood, for example, with veneer and interior plies having a higher moisture content than was previously possible. Generally, resins according to the invention may contain from about 1% to about 14%, and preferably from about 1% to about 7% by weight, of potassium hydroxide, or more.Type: GrantFiled: July 18, 1988Date of Patent: December 24, 1991Assignee: Borden, Inc.Inventor: Nick K. Daisy
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Patent number: 5071940Abstract: A curing agent mixture for curing alkaline phenol/formaldehyde resins containsA) a pulverulent or fibrous filler andB) a carbonic ester.Type: GrantFiled: February 8, 1990Date of Patent: December 10, 1991Assignee: BASF AktiengesellschaftInventors: Dieter Dormeyer, Winfried Kochersperger, Franz Wolf, Eberhard Pfuetze
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Patent number: 5057591Abstract: The invention is a solution of highly advanced phenolic resin with improved inherent foamability that is made from the reaction of phenol, aldehyde, water and alkali the improved foamability being brought about by the incorporation of up to 1.0% by weight, anhydrous basis, lime (calcium hydroxide) into the early stages of the reaction mix. In another embodiment, the invention is a plywood glue composition comprising a solution of lime-containing highly advanced phenolic resin, dried animal blood and preferably an aldehyde glue viscosity-lowering agent.Type: GrantFiled: August 25, 1988Date of Patent: October 15, 1991Assignee: Borden, Inc.Inventors: William D. Detlefsen, Lewis D. Creel, Lee R. Johnson
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Patent number: 5043412Abstract: A raw batch composition for use in making a shaped article such as a foundry shape or refractory article is disclosed. The composition comprises a mixture of an aggregate material; a phenol formaldehyde novolak resin; a phenol formaldehyde resole resin; and an ester functional curing agent. A shaped article prepared from the composition and processes for making a refractory body or foundry article are also disclosed.Type: GrantFiled: September 1, 1989Date of Patent: August 27, 1991Assignee: Borden, Inc.Inventors: Pitchaiya Chandramouli, Raja Iyer, Calvin Johnson
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Patent number: 4857207Abstract: A process for the purification of phenol-containing waters, in particular waste waters from phenolic resin production, where the term "phenol" is taken to mean all steam-volatile benzene derivatives according to DIN 38,409 H 16, by reaction of the phenol with formaldehyde in an alkaline environment at 50.degree. to 100.degree. C. to form those phenolformaldehyde condensates which, by subsequent acidification of the waste water, precipitate in filterable, granular and no longer sticky form and can be separated.Type: GrantFiled: April 8, 1988Date of Patent: August 15, 1989Assignee: Hoechst AGInventors: Ulrich Hars, Rolf Staiger, Karl Westphal
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Patent number: 4848443Abstract: Foundry molds and cores are prepared by using as a binder a phenolic resin in solution in aqueous sodium hydroxide and using an ester to cure the binder. The ester may be incorporated in the mixture prior to shaping, or the ester in gaseous form may be passed through the shaped mixture.Type: GrantFiled: July 27, 1987Date of Patent: July 18, 1989Assignee: Hepworth Minerals and Chemicals, LimitedInventors: Geoffrey W. Westwood, Raymond A. Higgins
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Patent number: 4841002Abstract: Compositions have melting points below 100.degree. C. which are useful in the formation of resins by reaction with polyphenolic compounds consisting of a mixture of more than two compounds having the formula ##STR1## wherein A represents a cyclic or acyclic aliphatic or substituted cyclic or acyclic aliphatic moiety having from 1 to 20 carbon atoms or an aromatic mono- or multi-nuclear or aliphatic substituted aryl residue having from 6 to 20 carbon atoms,R independently represents H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.6 H.sub.5,R.sup.1 independently represents H or CH.sub.3,R.sup.2 independently represents H or CH.sub.3, andx represents an integer from 0 to 2are described.Type: GrantFiled: November 8, 1988Date of Patent: June 20, 1989Assignee: Ashland Oil, IncInventors: Billy M. Culbertson, Omar Tiba
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Patent number: 4839446Abstract: A polymerizable thermosetting composition which is a flowable liquid at moderate temperatures which comprises a mixture of:(A) from about 75% to about 95% by weight of a mixture of:(1) from about 80% to about 20% by weight of a bisoxazoline and(2) from about 20% to about 80% by weight of a polyphenolic compound and(B) from about 5% to about 25% by weight of at least one member selected from the group consisting of a monooxazoline and a monooxazine,a method for forming thermoset products therefrom and the novel thermoset products resulting from said method are described.Type: GrantFiled: August 8, 1988Date of Patent: June 13, 1989Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba
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Patent number: 4785073Abstract: A series of melamine-phenol-formaldehyde resoles for pressure-free to low pressure, low/medium temperture conversion into moulded product. The molar ratio of melamine:phenol is the range 1:4.7 to 1:0.29; for each mole of melamine there are 1.5 to 3 moles of formaldehyde; and for each mole of phenol there are 1.2 to 2 moles of formaldehyde. The resin compositions may contain fillers/reinforcing fibers, glycols and water curing is at or near neutal pH and may be accelerated by the use of boric oxide or acid and also by microwave heating. Moulded products have good heat-and fire-resistance, and good smoke emission properties, and are non-toxic.Type: GrantFiled: April 11, 1985Date of Patent: November 15, 1988Assignee: Polymer Tectonics LimitedInventors: Robert Farkas, Lothar M. Hohmann
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Patent number: 4758478Abstract: It has now been found that when there is a partial or complete replacement of the sodium hydroxide that is used to make a sodium phenolate resole resin by a molar equivalent of potassium hydroxide, a far faster curing resin is obtained. Such potassium-modified phenoli resins exhibit significant improvement in cure speed without loss of flowability. To the contrary, these resins act as though they were lower molecular weight condensation products. Reduced application rates are possible. The combination of faster cure and lower application rates has allowed such resins to be used as effective adhesives for plywood, for example, with veneer and interior plies having a higher moisture content than was previously possible. Generally, resins according to the invention may contain from about 1% to about 15%, and preferably from about 1% to about 7% by weight, of potassium hydroxide, or more.Type: GrantFiled: September 30, 1986Date of Patent: July 19, 1988Inventors: Nick K. Daisy, Dale L. Leeper
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Patent number: 4661412Abstract: A fast-curing, melamine-modified phenolic laminating resin is described comprising the co-condensation product of aldehyde, phenol and melamine in a water-soluble organic solvent. The modified laminating resin exhibits sufficiently high penetration and curing characteristics for use in a low pressure, continuous laminating process.Type: GrantFiled: June 5, 1986Date of Patent: April 28, 1987Assignee: Georgia-Pacific Resins, Inc.Inventors: Leopold F. Bornstein, deceased, Gary P. Fillingame
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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: 4613662Abstract: A process comprising copolymerizing an oxazoline with a bis-or poly-phenolic compound in the presence of a catalyst which is a cationic complex of an alkali or an alkaline earth metal at a temperature in the range of from about 100.degree. to 200.degree. C. is described.Type: GrantFiled: August 7, 1985Date of Patent: September 23, 1986Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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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: 4611020Abstract: A fast-curing, melamine-modified phenolic laminating resin is described comprising the co-condensation product of aldehyde, phenol and melamine in a water-soluble organic solvent. The modified laminating resin exhibits sufficiently high penetration and curing characteristics for use in a low pressure, continuous laminating process.Type: GrantFiled: January 11, 1985Date of Patent: September 9, 1986Assignee: Georgia-Pacific Resins, Inc.Inventors: Leopold F. Bornstein, deceased, Gary P. Fillingame
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Patent number: 4608408Abstract: A phenol-resorcinol-formaldehyde resin and a method for making the same. In this method phenol and formaldehyde at an initial pH of 8.5 to 9.2 are reacted in the presence of a sodium sulfite catalyst. The reaction mixture is heated and refluxed until it has a viscosity of u-v on the Gardner bubble test. Additional resorcinol is added to the mixture and refluxing is continued until it has a viscosity of 30 to 100 Garner sections. The reaction mixture is diluted with a water miscible solvent to obtain a resin solution having a solids content of about 40 to 60 percent by weight and a viscosity of 2.0 to 3.5 poise. An alkali metal carbonate material in the amount of 4 to 8 percent by weight of the resin is added to make adhesives including this resin fast curing. Fumed silica is also added to the resin solution by means of high shear apparatus to make the solution thixotropic.Type: GrantFiled: April 24, 1985Date of Patent: August 26, 1986Assignee: Koppers Company, Inc.Inventors: Richard T. Hood, Raymond L. Bender
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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