Two Distinct Phenolic Reactants Or Two Or More Hydroxy Groups Or Phenate Groups Bonded To Nuclear Carbon Atoms Of The Same Benzene Ring Patents (Class 528/155)
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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: 4433129Abstract: This invention is directed to hemi-formals having the following formulas: ##STR1## wherein b is 1 to about 5, c is 1 to about 3, d is 0 to about 2, the sum of c and d does not exceed 3 and is equal to or greater than 1 and n has a value equal to or greater than 1. These materials can be used to manufacture phenolic resins and are adaptable to liquid injection molding processes.Type: GrantFiled: January 19, 1982Date of Patent: February 21, 1984Assignee: Union Carbide CorporationInventors: George L. Brode, Sui-Wu Chow
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Patent number: 4430491Abstract: Thermoplastic and thermoset polymeric compositions, having particular utility in the area of molding applications, are obtained by reacting a compound containing a plurality of oxazoline groups with a phenol or a phenolic resin each containing a plurality of aromatic hydroxyl groups.Type: GrantFiled: September 30, 1982Date of Patent: February 7, 1984Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Timothy A. Tufts
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Patent number: 4426484Abstract: The cure of resin compositions comprising a mixture of a resole type phenol aldehyde resin and a novolac type phenol formaldehyde resin is improved by employing resorcinol as all or part of the phenolic component in the novolac type resin. The resin compositions are particularly useful as binders for foundry sand.Type: GrantFiled: October 14, 1981Date of Patent: January 17, 1984Assignee: Sumitomo Durez Company, Ltd.Inventors: Yukio Saeki, Katsuyuki Tanaka
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Patent number: 4425178Abstract: The invention is an improved hardener for use with phenolresorcinol-formaldehyde wood bonding adhesives. The hardener is conveniently made and shipped as a stable dry powdered material. It is then slurried in water at the point of use for convenience with continuously mixed and dispensed liquid-liquid, two part adhesive systems. The hardener comprises paraformaldehyde or alphapolyoxymethylene, fillers, viscosity and/or rheology control agents, and a solid acidic material. The latter ingredient is a critical component used to adjust the pH of an aqueous slurry to the range of 4.0 to 5.5. Oxalic acid is preferred. In this pH range, the formaldehyde polymers are stable and the slurried hardener does not give off significant formaldehyde odor for periods up to several days. Bonding performance is improved because the characteristics of the hardener and resulting adhesive have very little variation over time.Type: GrantFiled: November 16, 1981Date of Patent: January 10, 1984Assignee: Weyerhaeuser CompanyInventor: William C. Grendon
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Patent number: 4424238Abstract: An adhesive having a high adhesive strength and capable of bonding firmly polyester fibrous material with rubber is disclosed, which comprises a mixture of components A and B in a mixing ratio of A/B of 100/5-100/30, said component A being formaldehyde condensate obtained by reacting formaldehyde with one member selected from the following members (1)-(4): (1) a mixture of resorcin with one of m-cresol, m-methoxyphenol, 3,5-xylenol and m-xylene, (2) a mixture of 5-methylresorcin with m-cresol or with m-methoxyphenol, (3) a mixture of m-cresol with p-chlorophenol and (4) m-cresol, and having substantially an average molecular weight of 300-600; and said component B being one member selected from the following members (5)-(7); (5) a formaldehyde condensate obtained by reacting formaldehyde with one of 3,5-xylenol, m-t-butylphenol and a mixture of m-cresol with m-t-butylphenol and having substantially an average molecular weight of 200-500, (6) 4,4'-thio-bis(6-t-butyl-3-methylphenol) and (7) 1,1'-bis(2,4-dihydroType: GrantFiled: April 6, 1982Date of Patent: January 3, 1984Assignee: Bridgestone Tire Company LimitedInventors: Toshihiro Yotsumoto, Kazuo Koyama
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Patent number: 4420571Abstract: Compositions useful as friction particles comprised of tri- and/or tetrafunctional phenol, difunctional phenol, aldehyde, a protective colloid, and a reaction promoting compound. The friction particles are formulated into friction elements. A process for producing the friction particles in particulate form.Type: GrantFiled: July 13, 1982Date of Patent: December 13, 1983Assignee: Union Carbide CorporationInventors: John R. Blickensderfer, Luba A. Pacala
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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: 4412014Abstract: Polyoxyalkylene foam stabilizing surfactants can be prepared by reacting a polyoxyalkylene adduct, a cyclic nitrogenous vinyl monomer and an esterified unsaturated dibasic acid under free radical polymerization conditions in the presence of a free radical initiator, and by subjecting the reaction product obtained to a solvent extraction. The isolated components can be utilized as surfactants in producing cellular foams.Type: GrantFiled: June 29, 1981Date of Patent: October 25, 1983Assignee: The Celotex CorporationInventors: Richard L. Frentzel, Ernest K. Moss
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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
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Patent number: 4404357Abstract: Novel resins are disclosed that are the reaction products of an aldehyde and an aromatic alcohol mixture of naphthol, preferably 1-naphthol, and a phenol. The molar ratio of the naphthol to the phenol in the reaction mixture can vary from about 20 to 1 to 1 to 20. The resins are formed by condensing the aldehyde with the aromatic alcohol mixture in the presence of an acid catalyst where the molar ratio of the aromatic alcohol to aldehyde is less than 1. The resins of the invention are characterized by melt temperature higher than the melt temperatures of conventional novolak resins.Type: GrantFiled: May 3, 1982Date of Patent: September 13, 1983Assignee: Shipley Company Inc.Inventors: Paul Taylor, Michael Gulla
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Patent number: 4404334Abstract: The present invention comprises a new phenolic-aldehyde based resinous, thermosetting polyol and a method for its production. According to the invention, phenol is condensed using acid catalysis, under freely evaporative atmospheric conditions with a molar excess of aldehyde, in the presence of polyhydroxyl component.Type: GrantFiled: November 18, 1982Date of Patent: September 13, 1983Assignee: Georgia-Pacific CorporationInventor: Leopold F. Bornstein
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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: 4396732Abstract: An amine resin soluble in water with the aid of an acid is produced by reacting a dihydric phenolic compound, such as a bisphenol, with a stoichiometric deficiency of preferably aromatic diepoxide, and then reacting the product containing less than -0.3 part of unreacted dihydric phenolic compound per part of reaction product with at least about 3.25 mol of formaldehyde per mol of said reaction product and with monosecondary amine to produce a Mannich base. This Mannich base is then reacted with additional diepoxide in an amount of from 0.5 to 2 epoxy equivalents per epoxy equivalent in the initially used diepoxide.Type: GrantFiled: July 13, 1981Date of Patent: August 2, 1983Assignee: DeSoto, Inc.Inventors: Kazys Sekmakas, Raj Shah
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Patent number: 4393189Abstract: A method of preparing a thermoplastic, water-soluble, phenolic aldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the aldehyde are reacted to less than 100 percent completion in an amount so that the aldehyde to phenolic compound ratio is in the range of about 0.6 to about 1.5 and at an acidic pH and for a period of time equivalent to about 3 hours to about 10 hours when the temperature is in the range of about 55.degree. F. (13.degree. C.) to about 90.degree. F. (32.degree. C.) to produce a resinous mixture. In the second stage the pH of the reaction is adjusted within the range above about 7.0 to about 7.Type: GrantFiled: November 16, 1981Date of Patent: July 12, 1983Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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Patent number: 4379897Abstract: 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 alkaline conditions with formaldehyde or a substance capable of generating formaldehyde.Type: GrantFiled: March 17, 1981Date of Patent: April 12, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Makoto Asano, Yoshimitu Tanabe, Hisamichi Murakami
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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: 4373062Abstract: Phenol-formaldehyde and phenol-resorcinol-formaldehyde resinous aqueous syrups useful as thermosetting binders or adhesives are prepared by reacting, a phenol-formaldehyde resin composition firstly at atmospheric reflux temperature at a substantially neutral pH of 5.8 to 8.5 and a formaldehyde to phenol mol ratio between 1.7 to 2.8 for a period of 20 to 120 minutes; reacting secondly with added formaldehyde, if necessary, and also needed alkali metal hydroxide to produce mol ratios of 2.1 to 2.8 and 0.10 to 0.38, respectively, per mol of phenol, for a period of at least two minutes at reflux to produce a liquid phenol-formaldehyde thermosetting resin. The setting time can be decreased, if desired, by using two portions of syrup, reacting one portion for a greater time-temperature period than the other and combining the two portions.Type: GrantFiled: April 20, 1981Date of Patent: February 8, 1983Inventor: Gordon E. Brown
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Patent number: 4366303Abstract: Particulate resoles are produced by mixing phenol, formaldehyde and amine in an aqueous medium containing a protective colloid. The resoles exhibit improved cure rate and sinter resistance when an alkaline compound is added to the reaction mixture after particulate formation.Type: GrantFiled: December 11, 1981Date of Patent: December 28, 1982Assignee: Union Carbide CorporationInventor: Peter W. Kopf
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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: 4343924Abstract: Disclosed is an improved method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary-amine catalyst. The pot life of the coating composition is substantially increased without deleterious loss of properties of the ultimately cured film wherein the coating composition comprises three components. The first component is a phenol-functional condensation product of (a) a phenol-aldehyde reaction product bearing a plurality of methylol and phenol groups, and (b) a polyol, polycarboxylic acid, or polyepoxide, wherein the condensation product is reacted with a selective transmethylolating agent for substantially transforming residual methylol groups into non-active hydrogen groups. The second component is a multi-isocyanate cross-linking agent and the third component is an organic solvent. The coating composition is applied to a substrate and cured by exposure of the coated substrate to a vaporous tertiary amine catalyst.Type: GrantFiled: September 14, 1981Date of Patent: August 10, 1982Assignee: Ashland Oil, Inc.Inventor: Gary L. Linden
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Patent number: 4340700Abstract: A process for preparing a resin containing phenolic groups, in which an aralkylene ether of formula ROCH.sub.2.Ar. CH.sub.2 OR, wherein Ar represents a phenylene group and R is an alkyl group of 1-4 carbon atoms, is reacted with a phenol containing 1-3 hydroxyl groups and at least 2 hydrogen atoms in the aromatic phenolic nucleus, wherein (1) an ether composition which comprises at least 50 molar % e.g. 50-100% of said ether and the remainder of said composition, if any i.e. up to 50% (such as 0.1-50%) is selected from aromatic compounds each with an Ar nucleus having two substituents selected from CH.sub.3, CH.sub.2 OR, CHO, CH(OR).sub.2, said phenol and (2) an added compound of formula R'CHO or R'CH (OR.sup.2).sub.2, wherein R' is monovalent phenyl group or substituted phenyl group, in which each substituent is an alkyl group of 1-4 carbon atoms or a chlorine atom, and R.sup.Type: GrantFiled: August 19, 1981Date of Patent: July 20, 1982Assignee: Albright & Wilson LimitedInventor: Alfred G. Edwards
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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: 4322300Abstract: A water-base well drilling, workover or completion fluid containing a fluid loss control agent prepared by pre-reacting sulfonated phenol with formaldehyde under alkaline conditions and then reacting the mixture with phenol under controlled conditions is described.Type: GrantFiled: May 27, 1980Date of Patent: March 30, 1982Assignee: Georgia-Pacific CorporationInventor: Howard W. Holmquist
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Patent number: 4314050Abstract: A method of preparing a thermoplastic, long-chain water-soluble, phenolic formaldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the formaldehyde are reacted to less than 100 percent completion in an amount so that the formaldehyde to resorcinol ratio is in the range of about 0.6 to about 2.0 and at an acidic pH and for a period of time equivalent to about 1 hour to about 20 hours when the temperature is in the range of about 30.degree. F.(-31 1.1.degree. C.) to about 122.degree. F. (50.degree. C.) to produce a resinous mixture having a predominant amount of trimer polymer along with minor amounts of dimer and higher oligomer polymers and along with unreacted phenolic compound and aldehyde. In the second stage the pH of the reaction is adjusted within the range above of about 7.0 to about 7.Type: GrantFiled: October 30, 1978Date of Patent: February 2, 1982Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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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: 4308180Abstract: A rubber composition comprising vulcanizable natural or synthetic rubber and a sulfide resin produced by (1) reacting a component (A) with a componet (B), followed by reacting with a component (D), or (2) reacting a component (A) with a component (B), followed by reacting with a component (C) and a component (D) simultaneously or sequentially, and if desired reacting the resulting phenol resin with an acylating agent, the component (A) being a phenol compound of the following formula, and/or an acylated compound thereof, ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom, a hydroxyl, carboxyl, amino, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkenyl or C.sub.7 -C.sub.12 aralkyl group or a phenyl group unsubstituted or substituted with at least one C.sub.1 -C.sub.Type: GrantFiled: March 19, 1980Date of Patent: December 29, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Haruki Okamura, Tetsuo Yamaguchi, Tamaki Ishii
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Patent number: 4277596Abstract: There is provided a molded shaped structure made by molding the reaction product of an organic resin and a modified magnesium silicate obtained by calcining chrysotile asbestos tailings. The new product is characterized by the absence of any fibers.Type: GrantFiled: April 8, 1980Date of Patent: July 7, 1981Assignee: Societe Nationale de l'AmianteInventor: Jean M. Lalancette
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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: 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: 4250031Abstract: A phenolic chelate resin comprising the three-dimensional product obtained by cross-linking a phenolic compound represented by the general formula (I): ##STR1## (wherein M is an alkali metal atom, an ammonium group, or a hydrogen atom, and R.sub.1 and R.sub.2, which may be the same or different, each is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms) with a phenol and an aldehyde. The phenolic chelate resin selectively adsorbs ferric ion and/or cupric ion in an acidic aqueous solution at a pH of 3 and less.Type: GrantFiled: September 18, 1979Date of Patent: February 10, 1981Assignee: Unitika Ltd.Inventors: Hiroyuki Uejima, Masahide Hirai, Masahiro Kazigase
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Patent number: 4246157Abstract: There are provided binder compositions particularly useful in the foundry art which are rapid curing and which comprise (A) a phenolic resin component including at least one resole or novolak resin, solvent comprising a mixture of (1) hydrocarbon solvent and (2) polar organic solvent containing at least sufficient organic phosphate and/or carbonate ester to increase the curing speed and solubility of the phenolic resin component, (B) an isocyanate component having a functionality of two or more and (C) sufficient catalyst to catalyze substantially completely the reaction between components (A) and (B). There is also provided a moldable composition comprising aggregate material, such as foundry sand, and such binder compositions and foundry cores or molds made therefrom and including a process for their manufacture from the moldable compositions by either "cold box" or "no-bake" procedures.Type: GrantFiled: March 7, 1979Date of Patent: January 20, 1981Assignee: Acme Resin CorporationInventor: Robert A. Laitar
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Patent number: 4241201Abstract: Phenolic novolak resins are described which are structurally characterized as having from about 55% to about 90% of the available theoretical paraphenyl linkages in the resin chain bridged to a phenyl group. The resin compositions of this invention provide extended resin stability at relatively low temperatures without significant adverse affect on the cure speed at the molding temperature. The resins are especially suited for use in runnerless injection or cold manifold molding processes, but can also be used in transfer, compression and injection molding processes.Type: GrantFiled: April 13, 1979Date of Patent: December 23, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventor: Myron C. Annis
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Patent number: 4238379Abstract: A primer, particularly for aluminum and aluminum alloys, that is free of alkaline materials and consists essentially of an aqueous solution of a water soluble condensation product of (1) phenol, resorcinol or a mixture of phenol and resorcinol and (2) formaldehyde.Type: GrantFiled: May 29, 1979Date of Patent: December 9, 1980Inventor: Theodore J. Reinhart, Jr.
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Process for the production of white melamine-phenol-aldehyde resins which are resistant to yellowing
Patent number: 4229557Abstract: Resins which are substantially white and resistant to yellowing are obtained by the addition of ammonium or alkali phosphates or ammonium or alkali borates during the production or processing of melamine-phenol-aldehyde resins in an aqueous basic medium, and by subsequently obtaining the resin by dehydration at a temperature of at least 70.degree. C.Type: GrantFiled: August 27, 1979Date of Patent: October 21, 1980Assignee: Ciba-Geigy CorporationInventors: Dieter Feinauer, Ludwig Streinz -
Patent number: 4226962Abstract: A novel metal modified novolak resin is prepared. The metal modified novolak resin is an electron acceptor and is further characterized by its compatability with the surface properties of a paper substrate. The metal modified novolak resin comprises a reaction product of a novolak resin and a metal salt. The novolak resin is a reaction product of a mixture containing a para-substituted phenol selected from the group consisting of paraalkylphenols having alkyl groups of about 1 to about 12 carbon atoms, para-phenylphenol and mixtures thereof, salicylic acid and formaldehyde.The novel metal modified novolak resin is prepared by heating a mixture containing one or more para-substituted phenols, salicylic acid, formaldehyde and an acid catalyst for a period of time sufficient to substantially completely react the phenols, salicylic acid and formaldehyde to form a melted novolak resin. The melted novolak resin is mixed with a zinc salt in an inert atmosphere to form the metal modified novolak resin.Type: GrantFiled: December 11, 1978Date of Patent: October 7, 1980Assignee: The Mead CorporationInventor: John J. Stolfo
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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: 4204020Abstract: A closed cell phenolic-resin foam material comprising phenolic-resin foam forming reactants, a blowing agent, and a surfactant which is the capped reaction product of an alkoxylated amine and a copolymerizable mixture of dialkyl maleate with N-vinyl-2- pyrrolidone or N-vinyl caprolactam.Type: GrantFiled: August 22, 1978Date of Patent: May 20, 1980Assignee: The Celotex CorporationInventors: John H. Beale, Ernest K. Moss
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Patent number: 4194071Abstract: There is disclosed a thermosetting phenolic resin composition, suitable for use in injection molding, which resin composition contains a molding grade phenolic resin and an effective amount of a reactive compound (e.g., para-t-butylphenol) that is capable of reducing the viscosity of molding compositions containing said phenolic resin compositon to a processable viscosity at a temperature at which the period of time within which said molding composition cures to a thermoset state is longer than the period of time that said molding composition is in the runner during a normal injection molding operation. There is also disclosed molding compositions containing said phenolic resin composition, and an injection molding process utilizing the same.Type: GrantFiled: February 11, 1976Date of Patent: March 18, 1980Assignee: Union Carbide CorporationInventor: Marvin E. Sauers
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Patent number: 4175065Abstract: A hardener composition for precondensates or liquid resins containing resorcinol and formaldehyde or resorcinol-phenol and formaldehyde and a method for glueing by using them. The hardener composition contains powdered paraformaldehyde suspended in a suspending agent that includes a precondensate of ketone and formaldehyde, which precondensate preferably contains water as a dilution media.Type: GrantFiled: May 12, 1978Date of Patent: November 20, 1979Assignee: AB CascoInventor: Sven-Erik Andersson
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Patent number: 4173684Abstract: A novel metal modified novolak resin is prepared. The metal modified novolak resin is an electron acceptor and is further characterized by its compatability with the surface properties of a paper substrate. The metal modified novolak resin comprises a reaction product of a novolak resin and a metal salt. The novolak resin is a reaction product of a mixture containing a para-substituted phenol selected from the group consisting of paraalkylphenols having alkyl groups of about 1 to about 12 carbon atoms, paraphenylphenol and mixtures thereof, salicylic acid and formaldehyde.The novel metal modified novolak resin is prepared by heating a mixture containing one or more para-substituted phenols, salicylic acid, formaldehyde and an acid catalyst for a period of time sufficient to substantially completely react the phenols, salicylic acid and formaldehyde to form a melted novolak resin. The melted novolak resin is mixed with a zinc salt in a inert atmosphere to form the metal modified novolak resin.Type: GrantFiled: September 6, 1977Date of Patent: November 6, 1979Assignee: The Mead CorporationInventor: John J. Stolfo
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Patent number: 4173470Abstract: A novolak resin suitable for use as a light-sensitive photoresist or maskant is prepared by reaction of at least one cresol with an aldehyde or reactive ketone and an aromatic hydroxyl compound having an alkyl side chain of from 3-15 carbon atoms. The addition of a conventional photosensitive agent yields a composition evidencing superior characteristics as compared with prior art novolak photoresists and which requires less sensitizer than such prior art resists.Type: GrantFiled: November 9, 1977Date of Patent: November 6, 1979Assignee: Bell Telephone Laboratories, IncorporatedInventors: Susan Fahrenholtz, David T. Long, Raymond C. Pitetti
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Patent number: 4168365Abstract: A flame-retardant phenolic resin which comprises the product obtained on(a) reacting at least one halogenated compound represented by the general formula (I) ##STR1## wherein A is --CH.dbd.CH.sub.2 or --O--CH.sub.2 --CH.dbd.CH.sub.2, X is a chlorine atom or a bromine atom, and n is an integer of 1, 2 or 3, with at least one phenol in the presence of an acidic catalyst; and(b) reacting the resulting reaction product with at least one phosphoric acid ester compound containing a phenolic OH group represented by the general formula (II), (III) or (IV). ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents an unsubstituted or substituted hydrocarbyl group, where R.sub.1 and R.sub.2 may be the same or different, and n is 1, 2 or 3, and at least one aldehyde or a precursor thereof in the presence of an acidic or alkali catalyst; and a process for producing the flame-retardant phenolic resin.Type: GrantFiled: November 30, 1977Date of Patent: September 18, 1979Assignee: Matsushita Electric Works, Ltd.Inventors: Hidekazu Takano, Toshiharu Mikawa, Kazuhiko Nemoto
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Patent number: 4151028Abstract: In the known process of co-use of a catechol-monophenol-formaldehyde condensation product and a "RFL" dip for bonding polyester fibres to the rubber in reinforced rubber articles, the use of the condensation product in the form of an alkanolamine salt instead of the ammonium salt, as hitherto used, leads to certain advantages. In addition to lowering a problem due to the evolution of ammonia fumes, there is on average a slight increase in bond strength and the compositions are more easily cleaned from the processing machinery used.Type: GrantFiled: August 21, 1978Date of Patent: April 24, 1979Assignee: Imperial Chemical Industries LimitedInventor: David C. Eaton
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Patent number: 4147643Abstract: Compositions useful as additives for fuels and lubricants can be made by reacting (A) an aromatic compound having an OH or SH group attached to an aromatic nucleus and an aromatic hydrogen atom (e.g., a substituted phenol wherein the substituent is an alkyl group of at least 50 carbon atoms); (B) an aldehyde or reactive equivalent thereof (e.g., formaldehyde); (C) a non-amino hydrogen, active hydrogen compound (e.g., a phenol, N,N-dimethyl aniline, etc.) and optionally, (D) an aliphatic alkylating agent of at least 12 carbon atoms (e.g., a polyisobutene of about 50 carbon atoms).Type: GrantFiled: June 17, 1976Date of Patent: April 3, 1979Assignee: The Lubrizol CorporationInventors: John F. Pindar, Jerome M. Cohen
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Patent number: 4140842Abstract: A closed cell phenolic-resin foam material comprising phenolic-resin foam forming reactants, a blowing agent, and a surfactant which is the capped reaction product of an alkoxylated amine and a copolymerizable mixture of dialkyl maleate with N-vinyl-2-pyrrolidone or N-vinyl caprolactam.Type: GrantFiled: September 29, 1977Date of Patent: February 20, 1979Assignee: The Celotex CorporationInventors: John H. Beale, Ernest K. Moss