Nitrogen-containing Reactant Is A Heterocyclic Ring Compound Containing At Least One Nitrogen Atom As A Ring Member Or Is Nitrogen-containing Aromatic Compound Patents (Class 528/163)
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Patent number: 5322915Abstract: A condensation polymer, obtainable by condensation of a mixture containing, as chief components,(A) from 90 to 99.9% molar of a mixture substantially consisting of(a) from 30 to 99% molar of melamine and(b) from 1 to 70% molar of a substituted melamine of the general formula I ##STR1## in which X, X', and X" are selected from the group consisting of --NH.sub.2, --NHR, and --NRR', and only one or two of X, X', and X" denote(s) --NH.sub.2, and R and R' are selected from the group consisting of hydroxy-C.sub.2 -C.sub.10 -alkyl, hydroxy-C.sub.2 -C.sub.4 -alkyl-(oxa-C.sub.2 -C.sub.4 -alkyl).sub.n, where n is an integer from 1 to 5, and amino-C.sub.2 -C.sub.12 -alkyl, or mixtures of melamines I, and(B) from 0.1 to 10% molar, based on (A) and (B), of unsubstituted phenols or phenols substituted by radicals selected from the group consisting of C.sub.1 -C.sub.9 -alkyl and hydroxy, or of C.sub.1 -C.sub.Type: GrantFiled: July 8, 1992Date of Patent: June 21, 1994Assignee: BASF AktiengesellschaftInventors: Juergen Weiser, Wolfgang Reuther, Rolf Fikentscher, Wolfgang Fath, Heinz Berbner, Hans D. Zettler, Heinz Voelker
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Patent number: 5302687Abstract: A process for preparing a polymeric composition comprising reacting a mixture of at least one phenolic compound and at least one oxazoline compound in the presence of a catalytic amount of at least one ammonium salt and a tetracarbyl phosphonium salt, and optionally also in the presence of an alkyl halide is described.Type: GrantFiled: March 29, 1993Date of Patent: April 12, 1994Assignee: Ashland Oil, Inc.Inventors: Billy M. Culbertson, Omar Tiba, Gilbert M. Gynn
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Patent number: 5296584Abstract: The invention relates to a composition consisting of a melamine solid suspended or dispersed in a resole resin. The method of the invention favors the intermolecular condensation polymerization reaction between phenol and melamine, rather than homopolymerization between phenol molecules or between melamine molecules. This invention reduces formaldehyde emissions by favoring a reaction whose by-product is water rather than formaldehyde. The compositions are useful for bonding glass fiber mats used for thermal and acoustical insulation.Type: GrantFiled: July 22, 1993Date of Patent: March 22, 1994Assignee: Borden, Inc.Inventor: Wayne R. Walisser
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Patent number: 5260405Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.Type: GrantFiled: October 26, 1992Date of Patent: November 9, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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Patent number: 5254639Abstract: A binding agent for molded bodies and molding compositions produced by prereacting a mixture of 5 to 60% by weight of lignin or a lignin fraction produced by the Organosolv process and 40 to 95% by weight of a phenol novolac resin and subjecting the latter to high shear forces in a kneader or extruder and optionally mixing the same with a curing agent useful in molding compositions and high temperature-stable molded products such as refractory products, friction coatings, textile fleeces and carbon or graphite materials.Type: GrantFiled: October 26, 1992Date of Patent: October 19, 1993Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
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Patent number: 5233012Abstract: Novel condensates comprising bisphenols and aromatic aminosulfonic acids, in particular, novel 4-aminobenzenesulfonic acid-2,2-bis (hydroxyphenyl)propaneformaldehyde condensates, and methods for their production are disclosed. The novel condensates are useful as a dispersant for disperse dyes, an additive for carbonaceous fine powder-water slurries and as a water reducing agent for cement.Type: GrantFiled: June 8, 1992Date of Patent: August 3, 1993Assignee: Sanyo-Kokusaku Pulp Co., Ltd.Inventors: Masanobu Kawamura, Shinji Hamada, Takashi Date, Toshihiro Sugiwaki, Nobuhiro Hanada
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Patent number: 5233001Abstract: A composition comprising a 1,2-dialkylidenecyclobutane such as 1,2-dimethylenecyclobutane, a diallyl compound and a polyimide such as a bismaleimide can be thermally cured to a tough copolymer having a high glass transition temperature.Type: GrantFiled: May 28, 1992Date of Patent: August 3, 1993Assignee: Shell Oil CompanyInventors: Larry S. Corley, Kent M. Hutton, Jr.
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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: 5176780Abstract: An adhesive having a content of a thermically curable oxazene resin which contains at least one 1-oxa-3-aza tetraline group in the molecule, optionally in combination with at least one curable epoxy compound, is used for bonding polyimide films to films of the same kind or to other substrates, particularly metal foils. Such bondings are highly heat-resistant and have an excellent peeling resistance. Therefore, they are suitable for the manufacture of printed circuit boards having high thermal stability and peeling resistance.Type: GrantFiled: May 20, 1991Date of Patent: January 5, 1993Assignee: Gurit-Essex AGInventors: Herbert Schreiber, Wolfgang Saur
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Patent number: 4973649Abstract: Novel thermosetting imido prepolymers having low melt viscosity, well adapted for the production, e.g., of preimpregnated shaped articles, are copolymerizates of at least one N,N'-bismaleimide; at least one hindered diprimary diamine, e.g., 4,4'-diamino-3,3',5,5'-tetraalkyl-diphenyl-methane or 1,3-diamino- or 1,4-diaminotrialkylbenzene; at least one comonomeric heterocycle, e.g., a vinylpyridine, N-vinyl-2-pyrrolidone, allyl isocyanurate, vinyltetrahydrofuran, and/or an imidazole compound; and at least one comonomeric (meth)acrylate.Type: GrantFiled: March 3, 1989Date of Patent: November 27, 1990Assignee: Rhone-Poulenc ChimieInventor: Yves Camberlin
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Patent number: 4960826Abstract: The titled compositions are useful binding adhesives, especially, for example, with engineered glass fiber-containing products, and the like. In the A-stage, the compositions are typically exceptionally water soluble and low temperature storage stable. Such compositions can be prepared initially by a procedure in which a resole or the like is copolymerized with free melamine(s) and is conditioned to include acidic stage conditioning. For example, phenol per se, formaldehyde and sodium hydroxide followed by melamine per se and aqueous sulfamic acid solution, with subsequent neutralization, can yield the exceptionally water soluble low temperature storage stable A-stage composition. The C-stage composition is non-punking and can be structurally hard and sound.Type: GrantFiled: February 19, 1988Date of Patent: October 2, 1990Assignee: Borden, Inc.Inventor: Wayne R. Walisser
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Patent number: 4904516Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.Type: GrantFiled: January 12, 1988Date of Patent: February 27, 1990Inventor: Albert W. Creamer
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Patent number: 4902770Abstract: The undercoating composition of the invention, useful for providing an undercoating layer for a top coat of a photosensitive resist layer on a substrate surface, comprises, as a principal ingredient thereof, a condensation product obtained by the condensation reaction between a hydroxy-substituted diphenylamine and a melamine compound substituted on the nitrogen atoms with methylol groups and/or alkoxymethyl groups. The undercoating obtained of the composition is highly resistant against the attack by the overcoating solution applied thereon so that the fidelity of the pattern reproduction by the photolithographic technique is greatly improved by virtue of the absence of any disorder at the interface between the undercoating and top coat layers. The advantage is further increased when the undercoating composition further comprises a photoextinctive agent, e.g. a dye, having absorptivity in the wave length region where the photosensitive resist of the top coat has sensitivity.Type: GrantFiled: May 20, 1987Date of Patent: February 20, 1990Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Wataru Ishii, Shozo Miyazawa, Shinji Tsuchiya, Hisashi Nakane, Akira Yokota
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Patent number: 4843143Abstract: An improved process for increasing the rate of the copolymerization of mixtures of polyphenolic compounds having more than two phenolic hydroxyl groups per molecule and bis-oxazolines comprising carrying out the copolymerization in the presence of a catalytic amount of a halohydrocarbon at a temperature in the range of from about 130.degree. C. to 150.degree. C. is described.Type: GrantFiled: April 18, 1988Date of Patent: June 27, 1989Assignee: Ashland Oil, Inc.Inventors: Billy M. Culberton, Omar Tiba
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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: 4806267Abstract: Compositions having 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 2as described.Type: GrantFiled: January 15, 1988Date of Patent: February 21, 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: 4774282Abstract: Novel curable resin compositions are disclosed containing an aromatic cyanate ester and an allyl ether of a bisphenol as a modifier. These compositions provide improved prepregs and composites. Additional modifiers including epoxy resins and bismaleimides may be included.Type: GrantFiled: November 20, 1986Date of Patent: September 27, 1988Assignee: Amoco CorporationInventor: Shahid P. Qureshi
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Patent number: 4748230Abstract: A process for the copolymerization of bis-2-oxazolines and polyphenolic compounds at greatly improved rates comprising carrying out the copolymerization in the presence of from about 0.5 to about 5% by weight of a phosphine catalyst is described.Type: GrantFiled: March 27, 1987Date of Patent: May 31, 1988Assignee: Ashland Oil, Inc.Inventors: Omar Tiba, Billy M. Culbertson, Marvin L. Deviney, Anil B. Goel
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Patent number: 4731430Abstract: Phenol resins which are modified with compounds possessing amide and/or imide groups and are based on phenol resol ethers bonded via o,o'-methylene ether groups, and a process for their preparation.The novel modified phenol resol ethers are useful for the preparation of coating systems, in particular as crosslinking agents for cathodic electrocoating binders, and for the preparation of adhesives and rubber assistants.Type: GrantFiled: July 9, 1986Date of Patent: March 15, 1988Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Juergen Nieberle
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Patent number: 4699970Abstract: The process for preparing a polymeric composition at improved rate comprising reacting an oxazoline compound and a phenolic compound in the presence of a catalytic amount of a phosphorous acid ester is described.Type: GrantFiled: June 30, 1986Date of Patent: October 13, 1987Assignee: Ashland Oil, Inc.Inventors: Omar Tiba, Billy M. Culbertson
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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: 4680375Abstract: Tricarbocyanine polymeric dyes have formulae I and II: ##STR1## where Y can be ##STR2## --S--, --Se-- or --O--, A can be ##STR3## in which R.sup.19 can be alkyl or --Cl, and p can be 0 or 1, R.sup.6 and R.sup.7 independently can be alkyl of (C.sub.1 -C.sub.30), preferably (C.sub.1 -C.sub.18),R.sup.4 and R.sup.5 independently can be --H, C.sub.6 H.sub.5 SO.sub.2 --, or CF.sub.3 SO.sub.2 --,Z can be --SO.sub.2 --, --CH.sub.2).sub.m, or vinylene,W can be I.sup.-, Br.sup.-, Cl.sup.-, ClO.sub.4.sup.-, PECHS.sup.- (polyethylcyclohexylsulfonate), F.sub.3 CSO.sub.3.sup.- (trifluoromethanesulfonate), or other commonly used dye anions,m is an integer of 1 to 20, andn is an integer of 5 to 10,000.Type: GrantFiled: March 11, 1985Date of Patent: July 14, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Mohamed A. Elmasry
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Patent number: 4675371Abstract: A process for the preparation of a thermoset polymer having good adhesive properties comprising reacting a compound containing a plurality of oxazoline groups with an alkenyl phosphonic acid at a temperature of from about room temperature to about 300.degree. C. is described.Type: GrantFiled: May 2, 1986Date of Patent: June 23, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4666997Abstract: Heat-curable mixtures comprising(a) 10-90% by weight of at least one compound of formula I ##STR1## (b) 90-10% by weight of at least one compound of formula II ##STR2## and, based on the sum of (a)+(b), (c) 0-30% by weight of at least one compound which is able to react with component (b),in which formulae above n, m, R, R', R.sub.1, R.sub.2 and R.sub.3 are as defined in claim 1, are suitable for the preparation of moulded articles such as prepregs and composites, coatings and bonds.Type: GrantFiled: September 9, 1985Date of Patent: May 19, 1987Assignee: Ciba-Geigy CorporationInventors: Alfred Renner, Sameer H. Eldin
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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: 4652620Abstract: The disclosure is directed to thermoset resinous compositions having utility in the area of surface coating and molding applications, the latter including the preparation of high performance composites and the use in reaction injection molding processes. The contemplated compositions are obtained by polymerizing a reaction mixture comprising a polyfunctional 2-oxazoline compound, a compound or oligomer containing a plurality of aromatic hydroxyl groups and a polyfunctional epoxide.Type: GrantFiled: October 4, 1985Date of Patent: March 24, 1987Assignee: Ashland Oil, Inc.Inventors: Timothy A. Tufts, Billy M. Culbertson
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Patent number: 4642264Abstract: The object of the present invention are new thermoset resins having quickened curing, a process for their preparation, and their applications. The resins according to the invention consist, at least in part, of the products resulting from the polycondensation of one or more pyridine derivatives containing at least two methyl groups in the 2, 4 or 6 positions, with one or more aromatic dialdehydes, and the addition of one or more additives consisting of phenol compounds. These resins are used to the fabrication of composite materials.Type: GrantFiled: August 23, 1984Date of Patent: February 10, 1987Assignees: Societe Nationale des Poudres et Explosifs, Office National d'Etudes et de Recherches AerospatialesInventors: Marcel Ropars, Bertrand Bloch
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Patent number: 4639505Abstract: The process for preparing novel polymers containing ether-amide groups by reaction of a bis- or poly-bicyclic amide acetal with a bis-phenolic or poly-phenolic material at a temperature of from about 80.degree. C. to 200.degree. C. is described.Type: GrantFiled: August 7, 1985Date of Patent: January 27, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4632966Abstract: A thermosetting resin composition comprising an N,N'-bismaleimide compound and an allylated phenol novolak resin having partially or wholly allyl-etherified phenolic hydroxyl groups and substantially no nucleous-substituted allyl group.Type: GrantFiled: October 10, 1985Date of Patent: December 30, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Shuichi Kanagawa, Hisao Takagishi, Teruho Adachi, Kunimasa Kamio
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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: 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: 4588760Abstract: Method and composition for modifying moisture retention of hair and thus improving its settability which comprises applying to hair an aqueous solution containing a heximinium salt and a resorcinol under conditions promoting in situ polymerization.Type: GrantFiled: August 9, 1985Date of Patent: May 13, 1986Assignee: Clairol IncorporatedInventors: Janusz Jachowicz, Leszek J. Wolfram
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Patent number: 4555544Abstract: In a process for hardening phenol-formaldehyde resol resins, comprising conducting the hardening of the resins with an acidic solution of water and/or an organic solvent having dissolved therein an aromatic sulphonic acid and/or concentrated sulphuric acid, the improvement comprising the hardening in the presence of aniline added to the phenolic resin beforehand in a quantity of between about 0.5 and 2% relative to the weight of the phenolic resin whereby the pot life is extended and the cure time is satisfactory, the resultant products being especially useful as prepegs.Type: GrantFiled: December 28, 1984Date of Patent: November 26, 1985Assignee: Societe Chimique des Charbonnages CDF Chimie, S.A.Inventors: Nicolas Meyer, Michel Cousin
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Patent number: 4546168Abstract: A thermosetting resin composition comprising (A) at least one dicyanamide compound and (B) at least one polyvalent imide having one or more unsaturated bonds and, if necessary (C) at least one polymerizable compound of epoxy compounds, phenolic compounds and triallyl isocyanurate compounds, and a prepolymer thereof obtained by subjecting the composition to a preliminary reaction with heating to the B stage can give a cured product having excellent heat resistance of class C and flexibility.Type: GrantFiled: August 9, 1984Date of Patent: October 8, 1985Assignee: Hitachi, Ltd.Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
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Patent number: 4500690Abstract: Heat resistant thermosetting prepolymers are prepared by reacting one or more methylated pyridines or pyrazines with one or more aromatic dialdehydes, and isopropenyl phenols. The prepolymers can be further reacted with bismaleimides to make prepolymers with lower cure temperatures and faster cure rates. The total number of methyl groups on the pyridine or pyrazine can vary from 2 to 4. The prepolymers are cured to produce heat resistant polymers and laminates with conventional fibers such as carbon fibers.Type: GrantFiled: May 11, 1984Date of Patent: February 19, 1985Assignee: The Dow Chemical CompanyInventor: Randy J. LaTulip
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Patent number: 4500691Abstract: Phenol-novolaks containing amino groups of formulas VI and VII ##STR1## wherein R.sup.1 is halogen, nitro, alkyl, alkoxy or phenyl, R.sup.2 is hydrogen, alkyl, cycloalkyl, phenyl or furfuryl, R.sup.3 is hydrogen or alkyl, R.sup.4 and R.sup.5 independently are alkyl, halogen, nitro or cyano, and x is 1 to 8, are obtained by reacting the corresponding phenol-novolak with an aldehyde or ketone of formula II ##STR2## and with a substituted aniline of formula III or IV ##STR3## in a molar ratio of 1 mol of phenol-novolak to 2 mols of compound of formula II and to 2 mols of compound of formula III or IV in an acid medium at a pH value of 0.5 to 3.0. The phenol-novolaks containing amino groups are useful curing agents for epoxy resins and are also suitable as starting compounds for the preparation of epoxy resins.Type: GrantFiled: January 6, 1984Date of Patent: February 19, 1985Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Theobald Haug
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Patent number: 4491654Abstract: A water-insoluble curing agent for epoxy resins, made by mixing a major amount by weight of a water-insoluble propylene diamine chosen from the group consisting of the C.sub.8 to C.sub.20 fatty propylene diamines and the C.sub.12 to C.sub.15 ether propylene diamines with a minor amount by weight of a water-soluble polyamine suitable for rapid cure of epoxy resins, mixing the resulting mixture with a water-insoluble substituted phenol to give a water-insoluble reaction product, and then reacting said reaction product with formaldehyde. A novel cured epoxy resin is produced by reacting the agent with an uncured epoxy resin, and the reaction can be done in a wet environment or even under water.Type: GrantFiled: July 11, 1984Date of Patent: January 1, 1985Inventor: Lowell O. Cummings
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Patent number: 4469859Abstract: A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) polyfunctional cyanate ester, prepolymer of the cyanate ester, or coprepolymer of the cyanate ester and an amine, and (b) cyclopentadiene or polycyclopentadiene and a curable resin composition comprising a mixture or a preliminary reaction product of above component (a), above component (b) and (c), a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine are disclosed. Cured resin having excellent impact-resistance, adhesive power, heat-resistance and chemical-resistance can be prepared from the compositions.Type: GrantFiled: July 10, 1980Date of Patent: September 4, 1984Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi
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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: 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: 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: 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: 4376849Abstract: A polyadduct/polycondensate which is water-dilutable when protonated with an acid, and which contains basic nitrogen groups, the groups being of the general formula (I) ##STR1## and/or of the general formula (II) ##STR2## as well as of the formula (III) ##STR3## where R.sup.1 and R.sup.2 are hydrogen or methyl, R.sup.3 and R.sup.4 are hydrogen, alkyl or a radical bonded to a phenol or phenolether, R.sup.5 and R.sup.6 are alkyl, hydroxyalkyl or alkoxyalkyl or are linked to one another to form a 5-membered or 6-membered ring, R.sup.7 is a polydienyl radical, n.sup.1 = from 0.5 to 3 and n.sup.2 = from 0.05 to 1.0, and its method of preparation.The polyadduct/polycondensate can be used, for example, as a surface-coating binder for the cathodic electrocoating of metal articles.Type: GrantFiled: July 9, 1981Date of Patent: March 15, 1983Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Eberhard Schupp
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Patent number: 4373086Abstract: A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of said cyanate esters, coprepolymers of said cyanate esters and an amine and mixtures thereof, (b) at least one compound having two or more acrylic ester groups represented by the formula ##STR1## wherein R.sup.1 is organic group comprising as member constituting a main chain or ring C and optionally O and/or N and optionally as a pendant hydroxy and/or halogen, when R.sup.1 contains aromatic group, R.sup.1 has 6-35 carbon atoms, and when R.sup.1 contains no benzene ring, R.sup.1 has 1-15 carbon atoms, X is hydrogen or methyl, n is integer of 2, 3, 4, 5 or 6 and valency of R.sup.1 is the same as n, and optionally (c) at least one compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides or coprepolymers of the maleimides and an amine is disclosed.Type: GrantFiled: February 3, 1981Date of Patent: February 8, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Nobuyuki Ikeguchi
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Patent number: 4371689Abstract: A curable resin composition comprising a mixture and/or a preliminary reaction product of (a) polyfunctional cyanate ester, prepolymer of the cyanate ester, or coprepolymer of the cyanate ester and an amine, and (b) alkenyl acrylic esters, alkenyl methacrylic esters, prepolymers of alkenyl acrylic esters, prepolymers alkenyl methacrylic esters, coprepolymers of alkenyl acrylic esters and alkenyl methacrylic esters and mixtures thereof, and a curable resin composition comprising a mixture or a preliminary reaction product of above component (a), above component (b) and (c) a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine are disclosed. Cured resin having excellent impact-resistance, adhesive power, heat-resistance and chemical-resistance can be prepared from the compositions.Type: GrantFiled: August 5, 1980Date of Patent: February 1, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi
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Patent number: 4346206Abstract: A process for preparing a thermosetting imide type prepolymer which comprises heating a bis-imide (A) and a diamine (B) in the presence of an organic solvent with a boiling point of 70.degree. to 170.degree. C. and heating the reaction mixture together with an epoxy compound (C). The imide type prepolymer prepared according to the process of the present invention has rapid curability and excellent solubility in low boiling point solvents such as acetone, methyl ethyl ketone and methyl cellosolve, which are available at low cost. Accordingly, the prepolymer is advantageously used especially for the production of laminated boards having good heat resisting properties, low moisture absorption and good adhesion to various substrates such as a copper foil.Type: GrantFiled: August 11, 1980Date of Patent: August 24, 1982Assignee: Hitachi Chemical Company, Ltd.Inventors: Akio Takahashi, Yutaka Itoh, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
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Patent number: 4343925Abstract: Coating compositions capable of liquid application to substrates consist essentially of a curable film forming polyol-containing component and an organic reactive diluent. The reactive diluent is an organic compound containing a primary or secondary hydroxyl group and further characterized by having a retained solids value of greater than about 80 percent, a hydroxyl equivalent weight of from about 180 to about 800, and a liquid viscosity of less than about 10 poise at 60.degree. C. The coating compositions can be formulated to contain little or no volatile organic solvent and/or water.Type: GrantFiled: December 7, 1979Date of Patent: August 10, 1982Assignee: PPG Industries, Inc.Inventors: Wen-Hsuan Chang, James B. O'Dwyer, John R. Peffer
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Patent number: 4319016Abstract: An ultraviolet-absorbing amino compound; a paint containing the aforesaid ultraviolet-absorbing amino compound; and a coated article having on its surface a coated film containing the aforesaid ultraviolet-absorbing amino compound are provided. The ultraviolet-absorbing amino compound is produced by reacting (a) a compound having a light absorption maximum within a wavelength region of 300 to 400 m.mu. and containing a mono-, di- or tetra-hydroxyphenyl group, (b) at least one compound containing a amino group and (c) formaldehyde, in the presence of at least one alcohol. The ultraviolet-absorbing amino compound of this invention is used in resin products which undergo photodegradation by ultraviolet light, for example, paints or molded articles of resins, and is especially effective for use in thermosetting synthetic resin paints.Type: GrantFiled: September 21, 1979Date of Patent: March 9, 1982Assignees: Kabushiki Kaisha Toyota Chuo Kenkyusho, Toyota Jidosha Kogyo Kabushiki Kaisha, Mitsui Toatsu Chemicals IncorporatedInventors: Moriji Kurobe, Ryusuke Tsuji, Eiichi Imao, Takayuki Masuyama, Eizi Nagata, Kazunori Kamada