Material Contains A Carboxylic Acid, Anhydride Thereof, Ester Thereof, Or Salt Thereof Patents (Class 528/144)
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Patent number: 5344909Abstract: A latent catalyzed phenolic resin composition is provided containing a thermosetting phenolic resole resin and a latent catalyst consisting essentially of a primary or secondary amine salt of a strong acid.Type: GrantFiled: June 3, 1993Date of Patent: September 6, 1994Assignee: Georgia-Pacific Resins, Inc.Inventors: David A. Hutchings, Ted M. McVay, Richard F. Pennock
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Patent number: 5334692Abstract: New, highly branched polyphosphonates which have a greatly improved flame retardant action compared with known polyphosphonates which are suitable as additives for plastics. In addition the new polyphosphonates may be incorporated in plastics as stabilizers with excellent migration properties.Type: GrantFiled: November 24, 1993Date of Patent: August 2, 1994Assignee: Bayer AktiengesellschaftInventors: Bernhard Hess, Wolfgang Schulz-Schlitte, Jurgen Kirsch, Dieter Freitag, Uwe Arndt, Hans-Georg Gehrke, Klaus Zander
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Patent number: 5319063Abstract: A phenolic resin can be obtained by a condensation reaction between a specific trifunctional aromatic compound and a phenolic compound. This resin can be reacted with a curing agent such as a hexamine to give cured articles having excellent heat resistance, electrical properties, wear resistance and chemical resistance, and the phenolic resin is also much more excellent in curing reactivity as compared with conventional techniques.Type: GrantFiled: January 15, 1993Date of Patent: June 7, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shinji Ando, Yukio Fukui, Shigeru Iimuro
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Patent number: 5243015Abstract: A latent catalyzed phenolic resin composition is provided containing a thermosetting phenolic resole resin and a latent catalyst consisting essentially of a primary or secondary amine salt of a strong acid.Type: GrantFiled: June 25, 1992Date of Patent: September 7, 1993Assignee: Georgia-Pacific Resins, Inc.Inventors: David A. Hutchings, Ted M. McVay, Richard F. Pennock
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Patent number: 5216111Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.Type: GrantFiled: October 22, 1990Date of Patent: June 1, 1993Assignee: Shipley Company Inc.Inventor: Anthony Zampini
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Patent number: 5216112Abstract: A phenolic resin can be obtained by a condensation reaction between a specific trifunctional aromatic compound and a phenolic compound. This resin can be reacted with a curing agent such as a hexamine to give cured articles having excellent heat resistance, electrical properties, wear resistance and chemical resistance, and the phenolic resin is also much more excellent in curing reactivity as compared with conventional techniques.Type: GrantFiled: August 15, 1991Date of Patent: June 1, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shinji Ando, Yukio Fukui, Shigeru Iimuro
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Patent number: 5206333Abstract: A copolycondensation of a phenol, a naphthol and formaldehyde proceeds smoothly in the presence of an acid and a metallic element selected from the group consisting of transition metallic elements and metallic elements of Group IIa, Group IIIa, Group IVa, Group Va and Group VIa of the Periodic Table, and a naphthol-modified phenolic resin which has a large molecular weight and does not gel is obtained.Type: GrantFiled: May 7, 1992Date of Patent: April 27, 1993Assignee: Hitachi Chemical Company, Ltd.Inventors: Haruaki Sue, Ken Nanaumi, Takuji Itou, Ken Madarame, Shinsuke Hagiwara
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Patent number: 5182357Abstract: One hundred percent thermosetting phenol/formaldehyde (P/F) resin and method of preparation thereof are disclosed. The resin comprises a molar ratio of F/P of about 1.2-1.7, has a softening point of about 80.degree. C. and cures at temperature of about 140.degree.-160.degree. C. The method comprises heating the reactants in a solvent-less system in the presence of an ortho directing catalyst while monitoring the amount of free formaldehyde present in the reaction system.Type: GrantFiled: October 22, 1991Date of Patent: January 26, 1993Assignee: DAP, Inc.Inventor: Gary L. Linden
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Patent number: 5155164Abstract: Products of the condensation of phenolmonosulfonic acids, dihydroxydiphenyl sulfones, urea and formaldehyde can be obtained by(A) preparing a homogeneous reaction mixture in sulfuric acid from the phenolmonosulfonic acid and dihydroxydiphenyl sulfone in the molar ratio of from 3:1 to 10:1, with the proviso that the water content of the mixture is not more than 10% of the total weight of the components, and the mixture contains from 0.3 to 1.5 moles of sulfuric acid per mole of dihydroxydiphenyl sulfone, at from 100.degree. to 180.degree. C.,(B) subsequently, at from 40.degree. to 90.degree. C., carrying out a precondensation with 1 to 2 moles of formaldehyde and 0.5 to 1.5 moles of urea per mole of phenol units present in aqueous medium,(C) partially neutralizing the reaction mixture,(D) adding to the partially neutralized reaction mixture 0 to 0.5 mole of phenol per mole of phenol units present and then 0.1 to 0.8 mole of formaldehyde per mole of phenol units then present,(E) further condensing at from 40.Type: GrantFiled: May 8, 1991Date of Patent: October 13, 1992Assignee: BASF AktiengesellschaftInventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
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Patent number: 5151496Abstract: The 2-functional component of substituted phenol-aldehyde novolac resins is reduced. Epoxy novolac resins prepared from the novolac resin containing reduced quantities of 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: December 18, 1991Date of Patent: September 29, 1992Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
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Patent number: 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: 5021522Abstract: An improved vulcanizable rubber composition of the type comprising (I) a rubber component selected from natural rubber, synthetic rubber or combinations thereof, and (II) a methylene donor compound which generates formaldehyde upon heating, and (III) a phenolic novolak resin type methylene acceptor compound is disclosed. The improvement comprises having at least ten mole percent of the phenolic groups of the phenolic novolak resin aralkylated with one or more compounds selected from the group consisting of styrene, alpha methyl styrene, beta methyl styrene, p-methyl styrene, alpha chloro styrene and vinyl naphthalenes.Type: GrantFiled: February 21, 1990Date of Patent: June 4, 1991Assignee: Indspec Chemical CorporationInventors: Bojayan Durairaj, Alex Peterson, Jr., Robert M. Lamars, Richard T. Hood
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Patent number: 4961795Abstract: A composition and a process for bonding lignocellulosic material under heat and pressure is disclosed. According to the process, a curing agent is combined with a binder which is an alkaline phenol-formaldehyde resin. In one aspect the combination is by injection into a line carrying the binder to application apparatus, followed by in-line mixing of the curing agent and binder and application of the mixture to the lignocellulosic material. The lignocellulosic material is then compressed and the binder cured. The curing agent may be an ester, a lactone or an organic carbonate. The effect of the curing agent may be moderated with an aliphatic mono or polyhydric alcohol.Type: GrantFiled: January 27, 1988Date of Patent: October 9, 1990Assignee: Borden, Inc.Inventors: William D. Detlefsen, Earl K. Phillips, Richard V. Norton
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Patent number: 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: 4939229Abstract: A method for preparing branched novolak polymers possessing excellent lithographic performance is provided. The method involves the acid catalyzed reaction of a phenol with a tris- or tetrakis(dialkylaminoalkyl)phenol followed by purification of the reaction product. The branched novolaks are soluble in aqueous base and organic solvent solutions and are particularly useful as the polymeric component of either positive acting or negative acting photoresist compositions.Type: GrantFiled: May 12, 1989Date of Patent: July 3, 1990Assignee: Rohm and Haas CompanyInventor: Leonard E. Bogan, Jr.
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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: 4876324Abstract: Orthocresol or a mixture of orthocresol and paracresol and an aldehyde compound or a derivative thereof are subjected to polycondensation in a solvent selected from an aliphatic alcohol having 3 to 12 carbon atoms, a glycol ether having 3 to 6 carbon atoms, benzyl alcohol and an aliphatic carboxylic acid having 2 to 6 carbon atoms, in the presence of an acid catalyst, to obtain linear and high molecular weight orthocresol-novolak resins or orthocresol/paracresol random copolymerized novolak resins which have a high softening point of 145.degree. C. or higher and a high number average molecular weight of 1500 or more and which are highly soluble in alcohols and ketones and are highly compatible with resins.Type: GrantFiled: May 13, 1987Date of Patent: October 24, 1989Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Yoshitomo Nakano, Masumi Kada
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Patent number: 4839457Abstract: A developing composition and a sheet for a pressure-sensitive copy paper comprising a phenolic resin as a main component which is obtained by condensating with formaldehyde using a p-substituted phenol with a 2,4-di-substituted and/or 2,6-di-substituted phenol, and zinc oxide which may be added thereto, as occasion demands.Type: GrantFiled: March 18, 1988Date of Patent: June 13, 1989Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kazuhide Hayama, Yukio Saitoh
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Patent number: 4745172Abstract: Phenolic resins obtained by condensation from alkylphenol, aldehyde, polyamine and polyether in a molar ratio of 1:0.7 to 1.3:0.005 to 0.2:0.001 to 0.3 are suitable as tackifiers for rubber mixtures.Type: GrantFiled: August 13, 1986Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Thomas Scholl, Reinhard Preuss, Manfred Abele, Hermann Fries, Theo Kempermann
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Patent number: 4698401Abstract: A polyfunctional reaction product having functional phenolic OH groups is made available by reacting a phenol and an alkoxylated amino-aldehyde condensation product in the presence of a solvent and of an acid catalyst. This method makes it possible to prepare a polyfunctional phenolic reaction product which is soluble in organic solvents at a low ratio of phenolic OH groups to alkoxy groups without gelling. The reaction product is particularly useful as a curing agent for epoxy resins.Type: GrantFiled: September 9, 1985Date of Patent: October 6, 1987Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Raymond Koenig
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Patent number: 4675375Abstract: Essentially phenol-free phenol resol ethers which are bonded via o,o'-methylene ether groups are prepared by a process in whichA. where the process is carried out beginning with the methylolation in an aqueous medium, the methylolation is carried out in the presence of 0.5-10% by weight, based on the phenol employed, of Me.sup.++ ions, the latter are then removed as a sparingly soluble salt, the water present as a solvent in the reaction mixture is removed at 30.degree.-80.degree. C. in the presence or absence of one or more monohydric, dihydric or trihydric alcohols and an entraining agent, and the water of reaction formed during the etherification is separated off at 45.degree.-120.degree. C., andB. where the process is carried out beginning with the methylolation in a non-polar organic solvent, the methylolation is carried out in the presence of 0.1-0.3% by weight, based on the phenol employed, of Me.sup.++ ions, the etherification is effected at 95.degree.-120.degree. C.Type: GrantFiled: June 13, 1985Date of Patent: June 23, 1987Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Juergen Nieberle
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Patent number: 4649188Abstract: The 2-functional content of phenol-aldehyde novolac resins is reduced by water extraction. Epoxy novolac resins prepared from the novolac resin containing less 2-functional product exhibit increased Tg values when cured.Type: GrantFiled: January 13, 1986Date of Patent: March 10, 1987Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Avis L. McCrary, Fermin M. Cortez
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Patent number: 4623686Abstract: The invention relates to novel compositions for coating purposes comprising(A) polyvinyl plastisols,(B) surface modified, finely divided, stabilized polyisocyanates with retarded reactivity, in which 0.1 to 25 equivalents-% of the isocyanate groups of the unstabilized polyisocyanate have been deactivated on the surface, preferably by a reaction with polyamines, hydrazine, alkylhydrazines, polyhydrazide compounds and/or selected amidine and/or guanidine compounds; and(C) plasticizers and/or lightly branched, relatively high molecular weight polyhydroxyl compounds having melting points below 60.degree. C. and compatible with PVC plastisol.The invention also relates to the use of these storage stable but heat curable mixtures as primers for PVC coatings on plastics, foils, textile sheet products or filaments and as primer coats for flocking.Type: GrantFiled: January 24, 1985Date of Patent: November 18, 1986Assignee: Bayer AktiengesellschaftInventors: Helmut Hurnik, Gerhard Grogler, Heinrich Hess, Richard Kopp
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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: 4480055Abstract: Amino-resin products, which include aminoplast foams, can be modified by reacting an aminoplast precondensate, which contains an excess of formaldehyde or to which supplemental formaldehyde or another lower monoaldehyde or dialdehyde has been added before processing, with a hardening agent or with a solution of hardening agent, surfactant, and foamer in the presence of an additive that consists of one or more mononuclear or binuclear phenols, phenolic ethers, or acenaphthene derivatives with the overall formulas ##STR1## in which X is H, OH, SO.sub.3 H, Cl, CH.sub.3, or C.sub.2 H.sub.5 andR is H or an alkyl radical, with 1 to 9 carbon atoms, at a pH between about 1 and 2, mixed if necessary with aromatic sulphonic acids, at a pH between about 1 and 2. The modified products can be employed wherever free formaldehyde is undesirable.Type: GrantFiled: February 26, 1982Date of Patent: October 30, 1984Assignee: Schaum-Chemie Wilhelm Bauer G.m.b.H. & Co. KGInventor: Heinz Baumann
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Patent number: 4403076Abstract: A fast curing shell molding composition having the tensile strength of a conventional novolac resin when cured contains a fast curing novolac resin comprising a methylene chained polyphenylol wherein a major portion of the methylene linkages are coupled to adjacent phenylol groups at the o-o' and p-p' position, wherein at least about 19% of the methylene linkages are coupled to adjacent phenylol groups at the o-o' portions, and wherein at least about 3% of the total number of methylene linkages are coupled to adjacent phenylol groups at the p-p' positions. The shell molding composition is produced from the fast curing novolac resin by uniformly coating refractory granules with the fast curing resin. The fast curing novolac resin can be prepared by blending a conventional novolac resin with a novolac resin having a large proportion of methylene linkages coupled to adjacent phenylol groups at the o-o' position.Type: GrantFiled: March 5, 1982Date of Patent: September 6, 1983Assignee: Pacific Resins & Chemicals, Inc.Inventor: Roderick A. McDonald
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Patent number: 4400492Abstract: Disclosed is a color-developer for pressure-sensitive recording sheets, comprising a co-condensate of a reaction intermediate of a p-substituted phenol and a trifunctional or higher phenol, or a polyvalent metal salt of said co-condensate, said reaction intermediate being obtained by the reaction of said p-substituted phenol under acidic conditions with formaldehyde or a substance capable of generating formaldehyde.Type: GrantFiled: March 24, 1981Date of Patent: August 23, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Makoto Asano, Saburo Kawashima, Yoshimitu Tanabe, Hisamichi Murakami
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Patent number: 4395535Abstract: A process for the manufacture of condensation products of phenols and isobutyraldehyde by reacting the phenols and isobutyraldehyde at elevated temperature in a mole ratio of 0.5:1 to 1.5:1 in the presence of acid or compounds hydrolyzable to acids as catalysts, subsequent neutralization and removal of the resultant reaction water by distillation wherein the reaction products obtained in this manner are also subjected to a water-vapor distillation.Type: GrantFiled: October 6, 1981Date of Patent: July 26, 1983Assignee: BASF AktiengesellschaftInventors: Juergen Nieberle, Karl-Clemens Peters, Wolfgang Reuther, Heinz-Hilmar Bankowsky
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Patent number: 4378453Abstract: An adhesive consisting comprising an alkoxyphenol derivative/resorcin derivative/formaldehyde cocondensate has a high adhesive strength and can bond firmly polyester fibrous material with rubber.Type: GrantFiled: April 6, 1982Date of Patent: March 29, 1983Assignee: Bridgestone Tire Co., Ltd.Inventors: Toshihiro Yotsumoto, Kazuo Koyama
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Patent number: 4376854Abstract: A process for preparing a resorcinol copolymer, comprising at least one specific phenol with formaldehyde at a certain mole ratio to obtain a resol-type precondensate containing 1 to 30% of residual unreacted formaldehyde and then adding said resol-type precondensate to a mixture of an acid catalyst and at least one resorcinol to effect co-condensation. The obtained copolymer is useful for an adhesive for polyester fiber and rubber.Type: GrantFiled: April 5, 1982Date of Patent: March 15, 1983Assignee: Hodogaya Chemical Co., Ltd.Inventors: Toyohiko Yamaguchi, Koichi Kashima, Nobuo Kaifu
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Patent number: 4374962Abstract: An adhesive comprising a cocondensate of formaldehyde with m-alkylphenol or its derivative and alkylresorcin is excellent in the adhesion, heat resistance and flexibility and can bond firmly polyester fibrous material with rubber.Type: GrantFiled: April 6, 1982Date of Patent: February 22, 1983Assignee: Bridgestone Tire Company LimitedInventors: Toshihiro Yotsumoto, Kazuo Koyama
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Patent number: 4362853Abstract: Carboxylate salts, prepared by a Mannich reaction and useful in the preparation of water-borne coatings, have the general formula ##STR1## where R.sup.1 represents an aliphatic, aromatic, or araliphatic divalent group which may contain a further --COO.sup.- M.sup.+ ; R.sup.2 represents --H, --CH(R.sup.3)N(R.sup.10)R.sup.1 COO.sup.- M.sup.+, or alkyl which may be substituted by --COO.sup.- M.sup.+, --CH(R.sup.3)OH, or --CH(R.sup.3)OR.sup.8, R.sup.1 and R.sup.2 containing together not more than one --COO.sup.- M.sup.+ ; R.sup.3 represents --H or alkyl; each R.sup.4 represents --H, halogen, alkyl, or alkenyl; R.sup.5 represents --H, halogen, alkyl, alkenyl, or a group --CH(R.sup.3)OH, --CH(R.sup.3)OR.sup.8, or --CHR.sup.3 --NR.sup.2 --R.sup.1 --COO.sup.- M.sup.+ ; either R.sup.6 represents --H and R.sup.7 represents the residue of a polyepoxide, preferably of average mol. wt. 1000-5000, or R.sup.6 represents a covalent bond linked to the group R.sup.7, and R.sup.Type: GrantFiled: October 13, 1981Date of Patent: December 7, 1982Assignee: Ciba-Geigy CorporationInventor: Christopher G. Demmer
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Patent number: 4350800Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.Type: GrantFiled: September 14, 1981Date of Patent: September 21, 1982Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
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Patent number: 4345061Abstract: This invention relates to cellular plastic compositions of condensation products of phenol-urea and formaldehyde useful for thermal and acoustical insulation and methods for their preparation in which the phenol is present in amounts of about 1 to about 20 percent by weight wherein the condensation product prior to foaming and setting as a rigid cellular plastic has a viscosity at room temperature of approximately 30 to 36 seconds, No. 1 Zahn cup, and a pH maintained in the range of about 6 to 8.Type: GrantFiled: December 15, 1980Date of Patent: August 17, 1982Assignee: C.P. Chemical Co., Inc.Inventor: Walter Hasselman, Jr.
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Patent number: 4337334Abstract: A process for producing a phenolic resin comprising condensing a phenol component and an aldehyde component, characterized in that the phenol component comprises (high-molecular-weight phenolic compounds which are left after bisphenol A-containing by-products formed in the production of bisphenol A by condensing acetone and phenol in the presence of an acid catalyst are treated at a high temperature of at least 150.degree. C. in the presence of an alkaline catalyst to remove low-boiling components therefrom.Type: GrantFiled: February 10, 1981Date of Patent: June 29, 1982Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Yoshiro Shimizu, Toshio Itakura, Mitsuhiro Iwasa, Kunio Hanauye
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Patent number: 4336366Abstract: Cationically polymerizable compounds, for example cyclic ethers, can be thermally polymerised if an aromatic iodonium salt of the formula I[(Ar.sup.1)(Ar.sup.2)I].sup.+ [MX.sub.n ].sup.- (I)in which Ar.sup.1 Ar.sup.2, M, X and n are as defined in claim 1, is used as the catalyst and an agent which forms free radicals on heating and has the formula III or IV ##STR1## in which R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.8 and m are as defined in claim 1, for example a benzpinacol silyl ether, is used as the co-catalyst. The process is of particular importance for heat-curing epoxide resins as a one-component system.Type: GrantFiled: February 20, 1981Date of Patent: June 22, 1982Assignee: Ciba-Geigy CorporationInventors: Godwin Berner, Rudolf Kirchmayr
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Patent number: 4318840Abstract: Binders for foundry core sand and other binder applications are produced from the tars resulting from production of bisphenol A.Type: GrantFiled: December 17, 1980Date of Patent: March 9, 1982Assignee: The Quaker Oats CompanyInventors: James E. Doyle, Russell B. Lembke
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Patent number: 4309527Abstract: Flame retardant polymer resins formed by an acid condensation reaction from a mixture of resorcinol and furfural with a molar excess of the aldehyde. In one particular embodiment the resin is formed of a mixture of two prepolymer solutions with at least a boric acid catalyst, one or both of the prepolymer solutions being an acid-condensation reaction product of resorcinol and furfural with excess aldehyde functionality, or one of the prepolymers being a mix of substantially unreacted resorcinol and furfural with a slight molar excess of aldehyde.Type: GrantFiled: February 9, 1981Date of Patent: January 5, 1982Assignee: Fiber Materials, Inc.Inventors: Lawrence E. McAllister, Herbert Dietrich
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Patent number: 4299947Abstract: A high-ortho phenolic novolac resin having excellent curability, heat stability and flowability can be produced safely at low cost by a process which comprises reacting a phenol and an aldehyde at a temperature of more than 100.degree. C. with (A) a catalyst effective for the addition reaction selected from the salts of divalent metals in combination with (B) a catalyst effective for the condensation reaction, or comprises reacting a phenol and an aldehyde under reflux in the presence of the catalyst (A), adding an acid to adjust the pH to 1-5, removing water under reduced pressure and then subjecting the product to reaction at a temperature of more than 100.degree. C. This process enables the addition reaction and the condensation reaction to proceed with a good balance, can solve problems arising in the prior process such as gelation, low yield and the like, and can produce a high-ortho type phenolic novolac resin safely at low cost. Accordingly, this process is quite advantageous in industry.Type: GrantFiled: June 11, 1980Date of Patent: November 10, 1981Assignee: Sumitomo Bakelite Company LimitedInventors: Motoyuki Nanjo, Tsutomu Watanabe, Shigeru Koshibe, Keiji Azuma
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Patent number: 4297473Abstract: Disclosed herein is a novel high-ortho phenolic novolac resin having excellent quick-curing property and thermal stability for use as phenolic resin molding material and perfectly free of divalent metal salt which is detrimental to the electrical properties of the molding material. This resin can be obtained by condensing a phenol and an aldehyde in an aldehyde/phenol molar ratio ranging from 0.6 to 1.0 and at a reaction temperature of more than 100.degree. C. at which the selectivity for condensation at the para-position is lowered (that is, the probability of the condensation at the ortho-position increases), with a weakly acidic catalyst having a specified dissociation constant (pKa value). The high-ortho phenolic novolac resin (having the specific molecular weight and ortho/para linkage ratio) obtained from said reaction is very useful for industrial applications as a phenolic injection molding material or epoxy/phenolic low-pressure encapsulation molding material with excellent electrical properties.Type: GrantFiled: May 9, 1980Date of Patent: October 27, 1981Assignee: Sumitomo Bakelite Company LimitedInventors: Shigeru Koshibe, Motoyuki Nanjo
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Patent number: 4281098Abstract: Phenol/aldehyde condensation reactions are short-stopped by the addition of an aqueous solution of a salt of a weak acid and a metal of Groups III to VIII of the Periodic Table.Type: GrantFiled: October 24, 1979Date of Patent: July 28, 1981Assignee: BP Chemicals LimitedInventor: Bryan H. McCormick
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Patent number: 4275170Abstract: Flame retardant polymer resins formed by an acid condensation reaction from a mixture of resorcinol and furfural with a molar excess of the aldehyde. In one particular embodiment the resin is formed of a mixture of two prepolymer solutions with at least a boric acid catalyst, one or both of the prepolymer solutions being an acid-condensation reaction product of resorcinol and furfural with excess aldehyde functionality, or one of the prepolymers being a mix of substantially unreacted resorcinol and furfural with a slight molar excess of aldehyde.Type: GrantFiled: September 7, 1979Date of Patent: June 23, 1981Assignee: Fiber Materials, Inc.Inventors: Lawrence E. McAllister, Herbert Dietrich
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Patent number: 4269949Abstract: A finished resin comprising a highly condensed phenol formaldehyde resole resin which has green groups formed by a low condensation phenol formaldehyde resin, the finished resin being modified by addition of a weak acid and a non-cellulosic protective colloid to improve reactivity and flow properties thereof.Type: GrantFiled: June 27, 1979Date of Patent: May 26, 1981Assignee: Borden, Inc.Inventors: Charles H. Hickson, Pitchaiya Chandramouli
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Patent number: 4268657Abstract: Improved friction elements suited for use for example in an automotive or similar brake or in a clutch are provided by employing therein as a binder the reaction product of phenol, formaldehyde, and monoalkylphenol having from 4 to about 20 carbon atoms in the alkyl group. The mole ratio range of phenol:alkylphenol:formaldehyde is about 2:1-5:1-7 and the number of moles of phenol and alkylphenol combined exceeds the number of moles of formaldehyde. An improved method of making friction elements is also provided which uses such binder.Type: GrantFiled: December 10, 1979Date of Patent: May 19, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Anthony P. Manzara
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Patent number: 4259473Abstract: Self-curing or curable materials are obtained from the distillation residues of coal hydrogenation by condensing a residue of this type having a softening point of 30.degree. to 54.degree. C. in a first stage with a mono- or dihydroxybenzene and/or a methylhydroxybenzene and/or an ethylene substituted benzene. These reactants are used at a ratio of residue to benzene derivative between 1:1 and 2:1 and the reaction is carried out in the presence of acid at a pH of 1 to 2 and at a temperature of 90.degree. to 100.degree. C. In a second stage the thus obtained reaction product is then further reacted at about the same temperature with an aldehyde. As a result a novolak-type resin is obtained. The invention permits the making of inexpensive self-curing or curable materials with properties similar to those of phenolic acids. Besides, the invention also provides an outlet for the high boiling residue of the extractive coal hydrogenation which otherwise had little use.Type: GrantFiled: January 15, 1980Date of Patent: March 31, 1981Assignee: Bergwerksverband GmbHInventors: Ingo Romey, Menachem El-Roy
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Patent number: 4259464Abstract: Cyclic phenol-aldehyde resins, for example cyclic tetramers; derivatives thereof; processes by which they are prepared; and uses thereof.Type: GrantFiled: May 13, 1976Date of Patent: March 31, 1981Assignee: Petrolite CorporationInventors: Rudolf S. Buriks, Allen R. Fauke, John H. Munch
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Patent number: 4239881Abstract: This invention relates to cellular plastic compositions of condensation products of phenol-urea and formaldehyde useful for thermal and acoustical insulation and methods for their preparation in which the phenol is present in amounts of about 1 to about 20 percent by weight wherein the condensation product prior to foaming and setting as a rigid cellular plastic has a viscosity at room temperature of approximately 30 to 36 seconds, No. 1 Zahn cup, and a pH maintained in the range of about 6 to 8.Type: GrantFiled: December 27, 1978Date of Patent: December 16, 1980Assignee: C.P. Chemical Company, Inc.Inventor: Walter Hasselman, Jr.
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Patent number: 4235989Abstract: Thermosetting water-immiscible phenol-formaldehyde resins in which a large proportion of the linkages between the benzene rings are benzyl ether linkages located ortho to the phenolic hydroxyl groups are produced by reaction of at least one mole of formaldehyde with 1 mole of phenol in an aqueous reaction medium in the presence of a metal carboxylate catalyst, such as, zinc acetate. Methods of control of the exothermic addition of formaldehyde to phenol are described.Type: GrantFiled: December 22, 1978Date of Patent: November 25, 1980Assignee: Cor Tech Research Ltd.Inventors: Sim Y. Leong, Pitchaiya Chandramouli, Ramesh C. Vasishth
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Patent number: 4221873Abstract: A method for producing a phenol foam plastic, consisting in that polycondensation of phenols with formaldehyde is conducted with simultaneous foaming and curing in the presence of a foaming agent and an acid or alkaline catalyst. Used as the phenols are pyrocatechol, hydroquinone, resorcinol, 5-methyl resorcinol, shale alkyl resorcinols, shale total phenols, or various combinations of said phenols. The method is simple and permits obtaining a foam plastic with improved physico-mechanical properties.Type: GrantFiled: April 17, 1978Date of Patent: September 9, 1980Inventors: Leonid V. Volodko, Mikhail A. Ksenofontov, Ljudmila E. Ostrovskaya, Galina G. Dzivitskaya, Igor D. Goretsky, Vasily M. Khoruzhy, Nikolai M. Denisjuk, Anatoly Y. Volokh, Oleg N. Pogorelsky
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Patent number: 4219634Abstract: Water-immiscible thermosetting phenol-formaldehyde resins in which a large proportion of the linkages between the benzene rings are benzyl ether linkages located ortho to the phenolic hydroxyl groups are produced by reaction of at least 1 mole of formaldehyde with 1 mole of phenol in an aqueous reaction medium in the presence of a metal carboxylate catalyst, such as, zinc acetate, in two stages, in which, in the first stage exothermic addition of formaldehyde to phenol occurs and, in the second stage, methylol phenol is polymerized to form the resin. Methods for control of the rate of polymerization, methods of separation of product resin from aqueous phase, methods of molecular weight distribution control, a semi-continuous operation and an alternative polymerization procedure are described.Type: GrantFiled: June 20, 1979Date of Patent: August 26, 1980Assignee: Cor Tech Research Ltd.Inventor: Ramesh C. Vasishth