Five-membered Heterocyclic Ring Contains At Least One Nitrogen Atom As A Ring Member Patents (Class 528/117)
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Patent number: 4600763Abstract: A process for the production of novel polymers by the interpolymerization of a bicyclic amide acetal, a dicarboxylic acid anhydride and a polyepoxide at a temperature in the range of from 80.degree. C. to about 200.degree. C. and at a pressure in the range of from about ambient to about 50 atmospheres is described.Type: GrantFiled: September 5, 1985Date of Patent: July 15, 1986Assignee: Ashland Oil, Inc.Inventor: Anil Goel
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Patent number: 4587311Abstract: There are described novel imidazolides (N-acylimidazoles) of the formula I ##STR1## wherein R.sub.1 is methyl, ethyl or isopropyl,R.sub.2, R.sub.3 and R.sub.4 independently of one another are each hydrogen, methyl, ethyl or isopropyl, with the proviso that R.sub.2 is hydrogen only when R.sub.1 is isopropyl,R.sub.5, R.sub.6 and R.sub.7 independently of one another are each hydrogen, methyl, ethyl or isopropyl, or phenyl which is unsubstituted or substituted by methyl or ethyl groups, with the proviso that at least one of the symbols R.sub.5, R.sub.6 and R.sub.7 is phenyl which is unsubstituted or substituted according to definition.The imidazolides (I) are suitable as curing agents for polyepoxide compounds.Type: GrantFiled: April 20, 1984Date of Patent: May 6, 1986Assignee: Ciba-Geigy CorporationInventors: Rolf Schmid, Helmut Zondler, Michael Fischer, Werner Stauffer
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Patent number: 4581421Abstract: The reaction product of imidazole and/or its alkyl derivatives and an aldehyde is described. Epoxy resins containing the product are useful in applications such as decorative coatings, encapsulations, adhesives, laminates, potting compounds, etc.Type: GrantFiled: May 6, 1985Date of Patent: April 8, 1986Assignee: Texaco, Inc.Inventors: Harold G. Waddill, George P. Speranza
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Patent number: 4579916Abstract: Heat-curable mixtures, containing (a) an epoxide resin having on average more than one epoxide group in the molecule, (b) an allyl-substituted or methallyl-substituted imide of the formula I ##STR1## in which E is allyl or methallyl, G is hydrogen or methyl, n is 1 or 2, and R is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, benzyl or arylene, and (c) a curing catalyst, have good storage stability and processability and produce moulded materials having high mechanical strength values and good resistance to heat.Type: GrantFiled: November 8, 1984Date of Patent: April 1, 1986Assignee: Ciba-Geigy CorporationInventors: Rolf Schmid, Alfred Renner, Werner Stauffer, Michael Fischer
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Patent number: 4559398Abstract: A curable composition consisting ofA. 100 parts by weight of an epoxy resin,B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, andC. from 0.1 to 5 parts by weight of an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl groupcan be used to produce moldings, coatings, finishes, adhesives and composite fiber materials.Type: GrantFiled: July 31, 1984Date of Patent: December 17, 1985Assignee: BASF AktiengesellschaftInventors: Helmut Tesch, Andreas Henne, Manfred Heym, Herbert Stutz
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Patent number: 4558115Abstract: Compositions comprising a material containing (a) alkenyl phenyl cyanate groups, (b) a material containing epoxide groups and optionally any one or more of (c) an aromatic polycyanate, (d) a polymaleimide or (e) a polymerizable ethylenically unsaturated aromatic material are curable to products having excellent mechanical, thermal and chemical resistant properties.Type: GrantFiled: March 11, 1985Date of Patent: December 10, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4555532Abstract: An epoxy resin composition containing as a latent hardener a diaminotriazine-modified imidazole compound and dicyandiamide is improved in the usable life of an solder resist ink composition and can give a solder resist also excellent in resistance to an electroless plating bath.Type: GrantFiled: October 10, 1984Date of Patent: November 26, 1985Assignee: Hitachi, Ltd.Inventors: Isamu Tanaka, Hiroshi Kikuchi, Akira Tomizawa, Hitoshi Oka
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Patent number: 4555563Abstract: Imide functional polyphenols are prepared by reacting an excess of a phenol with an unsaturated diimide which is prepared by reacting an unsaturated polycycloaliphatic dicarboxylic acid anhydride with a diamine.These materials are useful in the preparation of castings, coatings, laminates and the like.Type: GrantFiled: December 7, 1984Date of Patent: November 26, 1985Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Mary N. White
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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: 4537834Abstract: Metal, preferably divalent copper, cobalt or nickel, phthalocyanine tetraamines are used as curing agents for epoxides. The resulting copolymers have high thermal and chemical resistance and are homogeneous. They are useful as binders for laminates, e.g. graphite cloth laminate.Type: GrantFiled: April 11, 1984Date of Patent: August 27, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
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Patent number: 4533682Abstract: Adducts of imidazolidine compounds, such as the reaction product of ethylene diamine with cyclohexanone, are provided with organic polyepoxides, especially with low molecular weight polyepoxides where the imidazolidine acts as a chain extender, and the adduct is reacted with an acid to protonate at least 50% of the amine groups in the adduct. These protonated adducts can be dispersed in water to form dispersion which cure with various curing agents. Aqueous electrocoating baths can be provided which electrodeposit at the cathode.Type: GrantFiled: April 29, 1983Date of Patent: August 6, 1985Assignee: DeSoto, Inc.Inventors: Anthony J. Tortorello, Nestor P. Hansen, Kathryn M. Jarocki
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Patent number: 4529537Abstract: Liquid epoxy resin hardeners are mixtures of 2-ethyl-4-methylimidazole, ethyldimethylimidazole and/or diethylmethylimidazole isomers which can also contain other alkylimidazoles, and can be produced by distillation of the products obtained in the dehydrogenation of 2-ethyl-4-methylimidazoline.Type: GrantFiled: July 5, 1984Date of Patent: July 16, 1985Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Anton Frank
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Patent number: 4525572Abstract: A mixture consisting of a polymaleimide and a copolymerizable monomer or a prepolymer formed from these two compounds contains, as the polymerization catalyst, an ethane which is substituted by aromatic groups and hydroxyl groups or halogen (cf. formula II), such as benzpinacol. The mixture is stable on storage and heat-curable. It can be cured, while at the same time being shaped to give mouldings, sheet-like structures, laminates, adhesive bonds or foams, for example by casting or compression moulding.Type: GrantFiled: April 16, 1984Date of Patent: June 25, 1985Assignee: Ciba-Geigy CorporationInventors: Hermann Diethelm, Sheik A. Zahir
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Patent number: 4514556Abstract: The disclosure relates to a novel compound 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) represented by the structural formula ##STR1## A method is provided for producing the novel compound subjecting formaldehyde or a methylenizing agent to thermal reaction with 2-ethyl-4-methyl imidazole in the presence of a catalyst; and a method of curing an epoxy compound and a method of accelerating curing the epoxy compound and a method of inhibiting crystallization of 2-ethyl-4-methyl imidazole, respectively by use of the new compound.Type: GrantFiled: March 29, 1984Date of Patent: April 30, 1985Assignee: Shikoku Chemicals CorporationInventors: Natsuo Sawa, Toshihiro Suzuki, Shinji Okazaki
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Patent number: 4510272Abstract: A novel composition is described comprising an admixture of an unsaturated polyimide prepolymer essentially free of terminal amine groups and an epoxy resin having a homopolymerization temperature that is greater than the temperature at which the polyimide polymerizes. These compositions maintain the superior glass transition temperatures and moisture resistance of the polyimide while picking up the desirable handling properties of the epoxy. These compositions have excellent high temperature and moisture resistant properties and excellent storage stability. For instance, carbon composites made with these materials have exhibited 60% shear property retention at 450.degree. F. after being boiled in water for one week. Also described are prepregs comprising the novel composition, methods for curing the novel composition to obtain the superior properties, and articles of manufacture comprising the novel composition.Type: GrantFiled: March 16, 1983Date of Patent: April 9, 1985Assignee: Avco CorporationInventor: Raymond C. Loszewski
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Patent number: 4487914Abstract: A curable composition comprising an epoxy resin or a monoepoxide and a curing agent comprising a metal salt complex of an adduct of an imidazole and a monofunctional epoxy compound.Type: GrantFiled: February 16, 1984Date of Patent: December 11, 1984Assignee: National Research Development CorporationInventor: John M. Barton
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Patent number: 4480083Abstract: Adducts of oxazolidine compounds, such as the reaction product of monoethanol amine with cyclohexanone, are adducted with an organic polyepoxide and the adduct is reacted with an acid to protonate at least 50% of the amine groups in the adduct. These protonated adducts can be dispersed in water to form dispersions which cure with various curing agents. When all the epoxy groups are consumed by reaction with the oxazolidine, aqueous electrocoating baths can be formulated which may contain aminoplast resin or phenoplast curing agents.Type: GrantFiled: March 21, 1983Date of Patent: October 30, 1984Assignee: DeSoto, Inc.Inventors: Anthony J. Tortorello, Nestor P. Hansen
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Patent number: 4465830Abstract: Hydrazides of the formula ##STR1## are good curing agents for epoxy resin, in the formula R.sub.1 and R.sub.2 being each hydrogen atom, C.sub.1 -C.sub.8 alkyl radical or --CH.sub.2 CH.sub.2 SCH.sub.3, R being hydrogen atom or methyl radical. The curing agents are useful in formulating novel storable one-package, heat-curable epoxy resins-based compositions.Type: GrantFiled: October 3, 1983Date of Patent: August 14, 1984Assignee: Ajinomoto Company, IncorporatedInventors: Koji Takeuchi, Nobuo Ito, Masahiro Abe, Kiyomiki Hirai
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Patent number: 4459398Abstract: A one-part epoxy adhesive has been developed that cures rapidly at relatively low elevated temperatures and is based on a diglycidyl ether of bisphenol A (DGEBA), DGBE reacted with glycerol and natural oils, and a unique triple catalyst system of metal imidazole salt, dicyandiamide and a cyclic latent curing agent that liberates diethylenetriamine when heated.Type: GrantFiled: May 27, 1983Date of Patent: July 10, 1984Assignee: General Motors CorporationInventors: Thomas J. Dearlove, Richard P. Atkins
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Patent number: 4436892Abstract: Novel imidazolides (N-acylimidazoles) of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl or phenyl, and R.sub.2 is hydrogen, orR.sub.1 is ethyl, and R.sub.2 is methyl, orR.sub.1 is hydrogen, and R.sub.2 is phenyl or methyl, andR.sub.3 is a group of any one of the formulae II-VI ##STR2## wherein X.sub.1 is hydrogen, chlorine or NO.sub.2, and X.sub.2 is hydrogen or NO.sub.2.The imidazolides are suitable as curing agents for polyepoxide compounds.Type: GrantFiled: December 6, 1982Date of Patent: March 13, 1984Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Friedrich Lohse, Roland Moser
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Patent number: 4435560Abstract: The disclosure is concerned with a maleimide-diamine resin composition which is well soluble to a low boiling point solvent and is excellent in heat resistance. The composition is featured by containing a maleimide-diamine adduct having the general formula: ##STR1## wherein A is a mono-, di-, tri- or tetravalent organic group containing at least two carbon atoms, R.sub.1 through R.sub.6 are hydrogen atom, a lower alkyl group, a lower alkoxy group, chlorine atom, bromine atom, trifluoromethyl group, or trichloromethyl group, and m is an integer of 0-4.Type: GrantFiled: September 9, 1981Date of Patent: March 6, 1984Assignee: Hitachi, Ltd.Inventors: Akio Takahashi, Moloyo Wajima, Akio Nishikawa, Hirosada Morishita
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Patent number: 4431781Abstract: Paint binders and process of producing same water-soluble upon total or partial neutralization with inorganic or organic acids comprising the reaction product of an epoxy compound having at least two 1,2-epoxy groups with secondary oxazolidine amines and saturated or unsaturated carboxylic acids; said binders having a theoretical amine value of at least 35 mg KOH/g. The paint binders are particularly useful in paints formulated for cathodic deposition. Paints formulated with said binders exhibit good applicational characteristics including throwing power, and the cured films have good mechanical and chemical resistance.Type: GrantFiled: October 12, 1982Date of Patent: February 14, 1984Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 4427802Abstract: A curable composition, and composites comprising (A) an epoxy resin and (B) a heterocyclic compound prepared by reacting at least one aromatic or aliphatic polyamine compound having at least two amine groups, which are separated by no more than one carbon atom, with at least one carbonyl-containing compound selected from the group consisting of aldehydes and ketones.Type: GrantFiled: July 27, 1981Date of Patent: January 24, 1984Assignee: Hexcel CorporationInventors: Richard J. Moulton, John D. Neuner
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Patent number: 4424336Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a malenimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.Type: GrantFiled: September 16, 1982Date of Patent: January 3, 1984Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4420605Abstract: This invention provides a coating composition comprising at least one 1,2 epoxy resin, a modified imidazole catalyst, and a polyfunctional phenol or polyfunctional acid or dicyandiamide.Type: GrantFiled: August 26, 1982Date of Patent: December 13, 1983Assignee: Mobil Oil CorporationInventor: Marvin L. Kaufman
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Patent number: 4417010Abstract: A liquid curing agent for polyepoxides having terminal epoxide groups is made from a blend of a normally solid aliphatic polyol and a monoimidazole. Cured compositions made from the curing agent and the polyepoxide are useful in various types of plastics applications.Type: GrantFiled: February 2, 1983Date of Patent: November 22, 1983Assignee: Celanese CorporationInventor: David A. Shimp
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Patent number: 4401777Abstract: Disclosed is a curable resin composition comprising (a) at least one maleimide compound selected from the group consisting of N-(alkenylphenyl)maleimide derivatives, and dimers and polymers thereof and (b) one or more kinds of epoxy resins, each having at least one epoxy group in the unit molecule thereof. The resin composition may contain, besides the above two components, an amino compound as a further component (c). The resin composition may comprise a prepolymer of any two components among the three components (a), (b) and (c) and the remaining component. The resin compositions are useful as molding materials, for the fabrication of laminates, and as varnishes, including insulation varnishes and impregnating varnishes.Type: GrantFiled: October 20, 1981Date of Patent: August 30, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hikotada Tsuboi, Motoo Kawamata, Masayuki Oba, Nobuhito Koga
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Patent number: 4400490Abstract: Nylon compositions are prepared by anionic polymerization of at least 75% of a lactam with up to about 25% of an epoxy component in the presence of a basic catalyst and a promoter that can be used in lactam polymerization wherein, in a preferred embodiment, the epoxy component is a modified epoxy resin containing physical property enhancing constituents. The nylon compositions are prepared by mixing a fraction of a lactam with the epoxy component and the promotor to form liquid mixture A, mixing remaining lactam with the catalyst to form liquid mixture B, mixing liquid mixtures A and B in the ratio ranging from 1/1 to 4/1 to form liquid mixture C, injecting liquid mixture C into a mold maintained at a temperature of about 100.degree. to 200.degree. C. wherein a chemical reaction takes place whereby the liquid is converted to a solidified mass in less than about 2 minutes, and removing the nylon composition in the form of a molded object.Type: GrantFiled: January 18, 1982Date of Patent: August 23, 1983Assignee: The B.F. Goodrich CompanyInventor: Wei-Yeih W. Yang
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Patent number: 4393195Abstract: 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) acrylic epoxy esters, methacrylic epoxy esters, prepolymers of acrylic epoxy esters, prepolymers methacrylic epoxy esters, coprepolymers of acrylic epoxy esters and methacrylic epoxy 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: July 12, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi, Satoshi Ayano
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Patent number: 4392930Abstract: Diacrylates or dimethacrylates, which are compatible with water before exposure to actinic radiation but after such exposure form hard, insoluble, coatings which are resistant to organic solvents and to water, are made by reaction with (meth)acrylic acid, or with a dicarboxylic acid and a hydroxy group-containing (meth)acrylate, of epoxide groups in an advanced diepoxide resin containing groups of formula ##STR1## where R.sup.4 denotes a divalent (cyclo)aliphatic or araliphatic radical,each R.sup.15 denotes an alkyl group or each pair of R.sup.15 denotes a group of formula --CH.sub.2).sub.2 --, --C(R.sup.16 R.sup.17)CO--, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 --.sub.3, or --CO--.sub.2, wherein R.sup.16 and R.sup.17 each represent a hydrogen atom, an alkyl group, or, conjointly, a cycloaliphatic ring, andc is zero or 1.Type: GrantFiled: June 30, 1982Date of Patent: July 12, 1983Assignee: Ciba-Geigy CorporationInventors: Roderick D. Hathaway, Edward Irving, John S. Waterhouse
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Patent number: 4393188Abstract: A process for preparing a thermosetting maleimide type prepolymer which comprises reacting (A) a polyfunctional maleimide compound, (B) a bis-maleimide, (C) a diamine and (D) an epoxy compound. The maleimide 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: February 12, 1981Date of Patent: July 12, 1983Assignee: Hitachi Chemical Company, Ltd.Inventors: Akio Takahashi, Motoyo Wajima, Ritsuro Tada, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
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Patent number: 4384084Abstract: Hardenable mixtures which contain a polyepoxide compound with, on average, more than one epoxide group in the molecule, and a hardener of the formula I ##STR1## The symbol n is an integer from 3 to 5. The methylene carbon atoms can be substituted by one or two methyl or ethyl groups.The hardenable mixtures can be used, for example, in the fields of the protection of surfaces or of adhesives technology.Type: GrantFiled: February 10, 1982Date of Patent: May 17, 1983Assignee: Ciba-Geigy CorporationInventors: Friedrich Lohse, Dieter Trachsler, Roland Moser
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Patent number: 4383903Abstract: A photo-curable resin composition is disclosed comprising (i) 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 the cyanate esters, coprepolymers of the cyanate esters and an amine and mixtures thereof, (b) at least one compound selected from the group consisting of monomers having at least one olefinically double bond prepolymers of the monomers, liquid rubbers having one or more acryloyl or methacryloyl groups and mixtures thereof and optionally (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides, coprepolymers of the maleimides and an amine and mixtures thereof and (ii) a photo polymerization initiator or a photo sensitizer.Type: GrantFiled: April 3, 1981Date of Patent: May 17, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Satoshi Ayano, Morio Gaku, Nobuyuki Ikeguchi, Hidenori Kinbara, Yasunari Osaki
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Patent number: 4383090Abstract: Extremely rapid ambient curing of polyepoxide resins and mixtures of polyepoxide resins and polyacrylate esters is achieved by use of a curing system composed of at least one polymercaptan and at least one catalytic co-curing agent which is the condensation product of:(a) aliphatic amine or substituted aliphatic amine containing at least one primary aliphatic amine group where the aliphatic moiety is ethylene or greater with(b) at least one amino acid, its corresponding lactam or other amide forming derivative.Optionally, known Lewis Base catalysts for the epoxy/mercaptan reaction, such as tertiary amines, may also be used.Type: GrantFiled: September 28, 1981Date of Patent: May 10, 1983Assignee: Diamond Shamrock CorporationInventors: Allen T. Slocki, Brian J. Carr, John F. Simone
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Patent number: 4376844Abstract: Resin-forming polyepoxides are mixed with polyoxazolidinyl compounds or polymers containing pendant oxazolidinyl groups in which the carbon atom in the 2-position of the heterocyclic ring is substituted with saturated hydrocarbon groups, such as dialkyl, or with an alkylene group forming a saturated ring with the carbon atom in the 2-position of the oxazolidinyl ring to form, in the absence of water, a stable composition which can be stored in closed containers for months without undergoing gelation. When such compositions are spread into films and the films exposed to moisture at ambient temperature, e.g., to ambient air having a relative humidity of at least 20% and temperature of about 15.degree. to 25.degree. C., the polymer serves to react with and cure the polyepoxide.Type: GrantFiled: January 20, 1982Date of Patent: March 15, 1983Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Wayne E. Feely
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Patent number: 4374214Abstract: Resins are obtained from blends of epoxide and imide containing or derived compounds, which have good resistance to mechanical deformation at elevated temperatures and good adhesion to inorganic materials such as metals and ceramics. These resins are particularly useful for making composite materials and molded articles.Type: GrantFiled: March 3, 1981Date of Patent: February 15, 1983Assignee: General Electric CompanyInventors: Fred F. Holub, John T. Hoback
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Patent number: 4370467Abstract: A curable resin composition comprising (i) a catalytic composite comprising a peroxide and other catalytic component and (ii) a mixture or a preliminary reaction product of (a) a polyfunctional cyanate ester, prepolymer of the cyanate ester or coprepolymer of the cyanate ester and an amine and (b) a polyfunctional maleimide, prepolymer of the maleimide or coprepolymer of the maleimide and an amine and optionally (c) other component is disclosed. The composition cures rapidly at a low temperature and is preferable from view point of quantity production and workability. The composition is excellent in respect of adhering property, heat-resistance, moisture-resistance and chemical-resistance, and is useful for preparing laminated products, molded products, paint, powder paint, adhesive or varnish.Type: GrantFiled: July 3, 1980Date of Patent: January 25, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi
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Patent number: 4370465Abstract: Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.Type: GrantFiled: December 14, 1981Date of Patent: January 25, 1983Assignee: The Dow Chemical Co.Inventors: Ross C. Whiteside, Jr., Adolphus V. Gist, George A. Doorakian
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Patent number: 4369304Abstract: 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, (b) acrylic esters, methacrylic esters, prepolymers of acrylic esters, prepolymers methacrylic esters, coprepolymers of acrylic esters and methacrylic esters and mixtures thereof, 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: January 18, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Nobuyuki Ikeguchi
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Patent number: 4369302Abstract: 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 polyisocyanate compound selected from the group consisting of polyisocyanates, prepolymers of said polyisocyanates, coprepolymer of said polyisocyanates and an acid anhydride and mixtures thereof and (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymer of said maleimides, coprepolymers of said maleimides and an amine and mixtures thereof is disclosed.Type: GrantFiled: December 30, 1980Date of Patent: January 18, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Nobuyuki Ikeguchi, Yasunori Osaki
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Patent number: 4368317Abstract: A mixture for the preparation of novel cross-linked nitrogen-containing polyadducts, which contains(a) a N-cyanolactam of the formula I or II ##STR1## and (b) a monomeric or oligomeric organic compound having not less than 2 C atoms and not less than 2 hydroxyl groups.The mixture, with or without addition of a monohydroxy compound, can be used as a casting resin or adhesive, or for the production of foams or coatings.The symbols in the formula are all as defined in claim 1.Type: GrantFiled: May 11, 1981Date of Patent: January 11, 1983Assignee: Ciba-Geigy CorporationInventors: Friedrich Lohse, Dieter Trachsler
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Patent number: 4366302Abstract: Imide-anhydrides having the structure ##STR1## wherein 1 and 2 are certain cycloaliphatic or aromatic groups and Z is selected from certain imide-anhydride and other substituents have been found to provide cured epoxy resin systems characterized by high temperature stability and excellent mechanical and physical properties.Type: GrantFiled: June 15, 1981Date of Patent: December 28, 1982Assignee: Lord CorporationInventors: Raj N. Gounder, John T. Geary
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Patent number: 4360655Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a maleimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.Type: GrantFiled: June 1, 1981Date of Patent: November 23, 1982Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4358571Abstract: Imidazole or substituted imidazole is adducted with acrylate ester, an epoxy, or an isocyanate followed by neutralization with lower fatty acid or alkylene or aromatic dicarboxylic acid. The product is a curing agent which is combined with an epoxy resin to form a powder coating.Type: GrantFiled: March 10, 1981Date of Patent: November 9, 1982Assignee: Mobil Oil CorporationInventors: Marvin L. Kaufman, George F. Salathe
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Patent number: 4355058Abstract: Storage stable epoxy resin powder coating compositions are disclosed, which contain a solid epoxy resin and, as hardening agent, a blocked polyisocyanate compound or isocyanate terminated polymer, wherein the blocking agent is an imidazoline compound.Type: GrantFiled: August 14, 1978Date of Patent: October 19, 1982Assignee: Chemische Werke Huels AktiengesellschaftInventors: Rainer Gras, Johann Obendorf, Elmar Wolf
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Patent number: 4350804Abstract: The invention is directed to curable compositions comprising an azole-functional resin and a labile metal-ligand complex. The azole-functional resin is the reaction product of a monomeric or polymeric resin and a reactive N-heterocyclic compound containing at least two nuclear nitrogen atoms in a 5-membered ring structure capable of forming stable metal-ligand complexes. Mixtures of azole-functional resins also may be used with the labile-metal ligand complexes in the compositions of the invention.Type: GrantFiled: November 21, 1980Date of Patent: September 21, 1982Assignee: PPG Industries, Inc.Inventors: John S. Ostrowski, John F. Grunewalder, Nicholas T. Castellucci
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Patent number: 4350781Abstract: A polymer precursor containing an oxazolin-2-one ring is made by reacting (a) an amino-reactive group containing compound having at least two groups capable of entering into an addition or condensation reaction with primary or secondary aromatically-bound amino groups with (b) an aromatic amine having at least one primary or secondary aromatically-bound amino group and at least one condensed oxazolin-2-one ring. The reactants are used in quantities such that for each aromatically bound primary or secondary amino group there are from 0.95 to 5 groups present in the amino-reactive group containing compound which are capable of reacting with the amino group. These polymer precursors may be used to produce high molecular weight polymers useful in the production of solid molded products, adhesives, foam plastics and coatings.Type: GrantFiled: July 24, 1981Date of Patent: September 21, 1982Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Gerhard Grogler, Holger Meyborg
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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: 4341693Abstract: Oligomeric, essentially linear epoxide resins with chlorine-containing and/or bromine-containing benzimidazolone radicals in the oligomer chain are particularly suitable as flameproofing agents for thermosetting and thermoplastic polymers.Type: GrantFiled: June 15, 1981Date of Patent: July 27, 1982Assignee: Ciba-Geigy CorporationInventor: Lothar Buxbaum
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Patent number: 4340715Abstract: Imide-amines having the structure ##STR1## wherein ##STR2## are certain cycloaliphatic or aromatic groups and R and R individually are hydrogen, halogen, an alkyl group having from 1 to 4 carbon atoms, hydroxy, carboxyl, and amine and when taken together represent ##STR3## wherein R.sup.2 is the same as R and R.sup.1, have been found to provide cured epoxy resin systems characterized by high temperature stability and excellent mechanical and physical properties.Type: GrantFiled: May 26, 1981Date of Patent: July 20, 1982Assignee: Lord CorporationInventors: Raj N. Gounder, John T. Geary