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)
  • Patent number: 5322915
    Abstract: 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: Grant
    Filed: July 8, 1992
    Date of Patent: June 21, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Weiser, Wolfgang Reuther, Rolf Fikentscher, Wolfgang Fath, Heinz Berbner, Hans D. Zettler, Heinz Voelker
  • Patent number: 5302687
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: April 12, 1994
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba, Gilbert M. Gynn
  • Patent number: 5296584
    Abstract: 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: Grant
    Filed: July 22, 1993
    Date of Patent: March 22, 1994
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 5260405
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: November 9, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5254639
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: October 19, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5233012
    Abstract: 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: Grant
    Filed: June 8, 1992
    Date of Patent: August 3, 1993
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Masanobu Kawamura, Shinji Hamada, Takashi Date, Toshihiro Sugiwaki, Nobuhiro Hanada
  • Patent number: 5233001
    Abstract: 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: Grant
    Filed: May 28, 1992
    Date of Patent: August 3, 1993
    Assignee: Shell Oil Company
    Inventors: Larry S. Corley, Kent M. Hutton, Jr.
  • Patent number: 5206333
    Abstract: 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: Grant
    Filed: May 7, 1992
    Date of Patent: April 27, 1993
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Haruaki Sue, Ken Nanaumi, Takuji Itou, Ken Madarame, Shinsuke Hagiwara
  • Patent number: 5176780
    Abstract: 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: Grant
    Filed: May 20, 1991
    Date of Patent: January 5, 1993
    Assignee: Gurit-Essex AG
    Inventors: Herbert Schreiber, Wolfgang Saur
  • Patent number: 4973649
    Abstract: 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: Grant
    Filed: March 3, 1989
    Date of Patent: November 27, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventor: Yves Camberlin
  • Patent number: 4960826
    Abstract: 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: Grant
    Filed: February 19, 1988
    Date of Patent: October 2, 1990
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 4904516
    Abstract: 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: Grant
    Filed: January 12, 1988
    Date of Patent: February 27, 1990
    Inventor: Albert W. Creamer
  • Patent number: 4902770
    Abstract: 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: Grant
    Filed: May 20, 1987
    Date of Patent: February 20, 1990
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Wataru Ishii, Shozo Miyazawa, Shinji Tsuchiya, Hisashi Nakane, Akira Yokota
  • Patent number: 4843143
    Abstract: 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: Grant
    Filed: April 18, 1988
    Date of Patent: June 27, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culberton, Omar Tiba
  • Patent number: 4841002
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: June 20, 1989
    Assignee: Ashland Oil, Inc
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4839446
    Abstract: 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: Grant
    Filed: August 8, 1988
    Date of Patent: June 13, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4806267
    Abstract: 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: Grant
    Filed: January 15, 1988
    Date of Patent: February 21, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Omar Tiba
  • Patent number: 4785073
    Abstract: 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: Grant
    Filed: April 11, 1985
    Date of Patent: November 15, 1988
    Assignee: Polymer Tectonics Limited
    Inventors: Robert Farkas, Lothar M. Hohmann
  • Patent number: 4774282
    Abstract: 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: Grant
    Filed: November 20, 1986
    Date of Patent: September 27, 1988
    Assignee: Amoco Corporation
    Inventor: Shahid P. Qureshi
  • Patent number: 4748230
    Abstract: 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: Grant
    Filed: March 27, 1987
    Date of Patent: May 31, 1988
    Assignee: Ashland Oil, Inc.
    Inventors: Omar Tiba, Billy M. Culbertson, Marvin L. Deviney, Anil B. Goel
  • Patent number: 4731430
    Abstract: 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: Grant
    Filed: July 9, 1986
    Date of Patent: March 15, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Juergen Nieberle
  • Patent number: 4699970
    Abstract: 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: Grant
    Filed: June 30, 1986
    Date of Patent: October 13, 1987
    Assignee: Ashland Oil, Inc.
    Inventors: Omar Tiba, Billy M. Culbertson
  • Patent number: 4698401
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: October 6, 1987
    Assignee: The Dow Chemical Company
    Inventors: Dieter H. Klein, Raymond Koenig
  • Patent number: 4680375
    Abstract: 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: Grant
    Filed: March 11, 1985
    Date of Patent: July 14, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Mohamed A. Elmasry
  • Patent number: 4675371
    Abstract: 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: Grant
    Filed: May 2, 1986
    Date of Patent: June 23, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4666997
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: May 19, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Renner, Sameer H. Eldin
  • Patent number: 4661412
    Abstract: 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: Grant
    Filed: June 5, 1986
    Date of Patent: April 28, 1987
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Leopold F. Bornstein, deceased, Gary P. Fillingame
  • Patent number: 4652620
    Abstract: 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: Grant
    Filed: October 4, 1985
    Date of Patent: March 24, 1987
    Assignee: Ashland Oil, Inc.
    Inventors: Timothy A. Tufts, Billy M. Culbertson
  • Patent number: 4642264
    Abstract: 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: Grant
    Filed: August 23, 1984
    Date of Patent: February 10, 1987
    Assignees: Societe Nationale des Poudres et Explosifs, Office National d'Etudes et de Recherches Aerospatiales
    Inventors: Marcel Ropars, Bertrand Bloch
  • Patent number: 4639505
    Abstract: 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: Grant
    Filed: August 7, 1985
    Date of Patent: January 27, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4632966
    Abstract: 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: Grant
    Filed: October 10, 1985
    Date of Patent: December 30, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shuichi Kanagawa, Hisao Takagishi, Teruho Adachi, Kunimasa Kamio
  • Patent number: 4613662
    Abstract: 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: Grant
    Filed: August 7, 1985
    Date of Patent: September 23, 1986
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4611020
    Abstract: 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: Grant
    Filed: January 11, 1985
    Date of Patent: September 9, 1986
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Leopold F. Bornstein, deceased, Gary P. Fillingame
  • Patent number: 4588760
    Abstract: 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: Grant
    Filed: August 9, 1985
    Date of Patent: May 13, 1986
    Assignee: Clairol Incorporated
    Inventors: Janusz Jachowicz, Leszek J. Wolfram
  • Patent number: 4555544
    Abstract: 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: Grant
    Filed: December 28, 1984
    Date of Patent: November 26, 1985
    Assignee: Societe Chimique des Charbonnages CDF Chimie, S.A.
    Inventors: Nicolas Meyer, Michel Cousin
  • Patent number: 4546168
    Abstract: 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: Grant
    Filed: August 9, 1984
    Date of Patent: October 8, 1985
    Assignee: Hitachi, Ltd.
    Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
  • Patent number: 4500690
    Abstract: 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: Grant
    Filed: May 11, 1984
    Date of Patent: February 19, 1985
    Assignee: The Dow Chemical Company
    Inventor: Randy J. LaTulip
  • Patent number: 4500691
    Abstract: 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: Grant
    Filed: January 6, 1984
    Date of Patent: February 19, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Stockinger, Theobald Haug
  • Patent number: 4491654
    Abstract: 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: Grant
    Filed: July 11, 1984
    Date of Patent: January 1, 1985
    Inventor: Lowell O. Cummings
  • Patent number: 4469859
    Abstract: 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: Grant
    Filed: July 10, 1980
    Date of Patent: September 4, 1984
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4454298
    Abstract: 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: Grant
    Filed: December 23, 1982
    Date of Patent: June 12, 1984
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4430491
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: February 7, 1984
    Assignee: Ashland Oil, Inc.
    Inventors: Billy M. Culbertson, Timothy A. Tufts
  • Patent number: 4414379
    Abstract: 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: Grant
    Filed: June 16, 1982
    Date of Patent: November 8, 1983
    Assignees: Kanebo Ltd., Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4404357
    Abstract: 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: Grant
    Filed: May 3, 1982
    Date of Patent: September 13, 1983
    Assignee: Shipley Company Inc.
    Inventors: Paul Taylor, Michael Gulla
  • Patent number: 4376849
    Abstract: 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: Grant
    Filed: July 9, 1981
    Date of Patent: March 15, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Eberhard Schupp
  • Patent number: 4373086
    Abstract: 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: Grant
    Filed: February 3, 1981
    Date of Patent: February 8, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Nobuyuki Ikeguchi
  • Patent number: 4371689
    Abstract: 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: Grant
    Filed: August 5, 1980
    Date of Patent: February 1, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4346206
    Abstract: 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: Grant
    Filed: August 11, 1980
    Date of Patent: August 24, 1982
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akio Takahashi, Yutaka Itoh, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
  • Patent number: 4343925
    Abstract: 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: Grant
    Filed: December 7, 1979
    Date of Patent: August 10, 1982
    Assignee: PPG Industries, Inc.
    Inventors: Wen-Hsuan Chang, James B. O'Dwyer, John R. Peffer
  • Patent number: 4319016
    Abstract: 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: Grant
    Filed: September 21, 1979
    Date of Patent: March 9, 1982
    Assignees: Kabushiki Kaisha Toyota Chuo Kenkyusho, Toyota Jidosha Kogyo Kabushiki Kaisha, Mitsui Toatsu Chemicals Incorporated
    Inventors: Moriji Kurobe, Ryusuke Tsuji, Eiichi Imao, Takayuki Masuyama, Eizi Nagata, Kazunori Kamada