Five-membered Heterocyclic Ring Contains At Least One Nitrogen Atom As A Ring Member Patents (Class 528/117)
  • Patent number: 4600763
    Abstract: 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: Grant
    Filed: September 5, 1985
    Date of Patent: July 15, 1986
    Assignee: Ashland Oil, Inc.
    Inventor: Anil Goel
  • Patent number: 4587311
    Abstract: 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: Grant
    Filed: April 20, 1984
    Date of Patent: May 6, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schmid, Helmut Zondler, Michael Fischer, Werner Stauffer
  • Patent number: 4581421
    Abstract: 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: Grant
    Filed: May 6, 1985
    Date of Patent: April 8, 1986
    Assignee: Texaco, Inc.
    Inventors: Harold G. Waddill, George P. Speranza
  • Patent number: 4579916
    Abstract: 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: Grant
    Filed: November 8, 1984
    Date of Patent: April 1, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schmid, Alfred Renner, Werner Stauffer, Michael Fischer
  • Patent number: 4559398
    Abstract: 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: Grant
    Filed: July 31, 1984
    Date of Patent: December 17, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Tesch, Andreas Henne, Manfred Heym, Herbert Stutz
  • Patent number: 4558115
    Abstract: 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: Grant
    Filed: March 11, 1985
    Date of Patent: December 10, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4555532
    Abstract: 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: Grant
    Filed: October 10, 1984
    Date of Patent: November 26, 1985
    Assignee: Hitachi, Ltd.
    Inventors: Isamu Tanaka, Hiroshi Kikuchi, Akira Tomizawa, Hitoshi Oka
  • Patent number: 4555563
    Abstract: 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: Grant
    Filed: December 7, 1984
    Date of Patent: November 26, 1985
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Mary N. White
  • 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: 4537834
    Abstract: 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: Grant
    Filed: April 11, 1984
    Date of Patent: August 27, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
  • Patent number: 4533682
    Abstract: 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: Grant
    Filed: April 29, 1983
    Date of Patent: August 6, 1985
    Assignee: DeSoto, Inc.
    Inventors: Anthony J. Tortorello, Nestor P. Hansen, Kathryn M. Jarocki
  • Patent number: 4529537
    Abstract: 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: Grant
    Filed: July 5, 1984
    Date of Patent: July 16, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Anton Frank
  • Patent number: 4525572
    Abstract: 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: Grant
    Filed: April 16, 1984
    Date of Patent: June 25, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Diethelm, Sheik A. Zahir
  • Patent number: 4514556
    Abstract: 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: Grant
    Filed: March 29, 1984
    Date of Patent: April 30, 1985
    Assignee: Shikoku Chemicals Corporation
    Inventors: Natsuo Sawa, Toshihiro Suzuki, Shinji Okazaki
  • Patent number: 4510272
    Abstract: 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: Grant
    Filed: March 16, 1983
    Date of Patent: April 9, 1985
    Assignee: Avco Corporation
    Inventor: Raymond C. Loszewski
  • Patent number: 4487914
    Abstract: 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: Grant
    Filed: February 16, 1984
    Date of Patent: December 11, 1984
    Assignee: National Research Development Corporation
    Inventor: John M. Barton
  • Patent number: 4480083
    Abstract: 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: Grant
    Filed: March 21, 1983
    Date of Patent: October 30, 1984
    Assignee: DeSoto, Inc.
    Inventors: Anthony J. Tortorello, Nestor P. Hansen
  • Patent number: 4465830
    Abstract: 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: Grant
    Filed: October 3, 1983
    Date of Patent: August 14, 1984
    Assignee: Ajinomoto Company, Incorporated
    Inventors: Koji Takeuchi, Nobuo Ito, Masahiro Abe, Kiyomiki Hirai
  • Patent number: 4459398
    Abstract: 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: Grant
    Filed: May 27, 1983
    Date of Patent: July 10, 1984
    Assignee: General Motors Corporation
    Inventors: Thomas J. Dearlove, Richard P. Atkins
  • Patent number: 4436892
    Abstract: 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: Grant
    Filed: December 6, 1982
    Date of Patent: March 13, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Helmut Zondler, Friedrich Lohse, Roland Moser
  • Patent number: 4435560
    Abstract: 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: Grant
    Filed: September 9, 1981
    Date of Patent: March 6, 1984
    Assignee: Hitachi, Ltd.
    Inventors: Akio Takahashi, Moloyo Wajima, Akio Nishikawa, Hirosada Morishita
  • Patent number: 4431781
    Abstract: 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: Grant
    Filed: October 12, 1982
    Date of Patent: February 14, 1984
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 4427802
    Abstract: 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: Grant
    Filed: July 27, 1981
    Date of Patent: January 24, 1984
    Assignee: Hexcel Corporation
    Inventors: Richard J. Moulton, John D. Neuner
  • Patent number: 4424336
    Abstract: 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: Grant
    Filed: September 16, 1982
    Date of Patent: January 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4420605
    Abstract: 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: Grant
    Filed: August 26, 1982
    Date of Patent: December 13, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Marvin L. Kaufman
  • Patent number: 4417010
    Abstract: 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: Grant
    Filed: February 2, 1983
    Date of Patent: November 22, 1983
    Assignee: Celanese Corporation
    Inventor: David A. Shimp
  • Patent number: 4401777
    Abstract: 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: Grant
    Filed: October 20, 1981
    Date of Patent: August 30, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hikotada Tsuboi, Motoo Kawamata, Masayuki Oba, Nobuhito Koga
  • Patent number: 4400490
    Abstract: 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: Grant
    Filed: January 18, 1982
    Date of Patent: August 23, 1983
    Assignee: The B.F. Goodrich Company
    Inventor: Wei-Yeih W. Yang
  • Patent number: 4393195
    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) 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: Grant
    Filed: August 5, 1980
    Date of Patent: July 12, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi, Satoshi Ayano
  • Patent number: 4392930
    Abstract: 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: Grant
    Filed: June 30, 1982
    Date of Patent: July 12, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Roderick D. Hathaway, Edward Irving, John S. Waterhouse
  • Patent number: 4393188
    Abstract: 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: Grant
    Filed: February 12, 1981
    Date of Patent: July 12, 1983
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Akio Takahashi, Motoyo Wajima, Ritsuro Tada, Hirosada Morishita, Yutaka Mizuno, Shunya Yokozawa, Kenji Tsukanishi
  • Patent number: 4384084
    Abstract: 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: Grant
    Filed: February 10, 1982
    Date of Patent: May 17, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Dieter Trachsler, Roland Moser
  • Patent number: 4383903
    Abstract: 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: Grant
    Filed: April 3, 1981
    Date of Patent: May 17, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Satoshi Ayano, Morio Gaku, Nobuyuki Ikeguchi, Hidenori Kinbara, Yasunari Osaki
  • Patent number: 4383090
    Abstract: 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: Grant
    Filed: September 28, 1981
    Date of Patent: May 10, 1983
    Assignee: Diamond Shamrock Corporation
    Inventors: Allen T. Slocki, Brian J. Carr, John F. Simone
  • Patent number: 4376844
    Abstract: 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: Grant
    Filed: January 20, 1982
    Date of Patent: March 15, 1983
    Assignee: Rohm and Haas Company
    Inventors: William D. Emmons, Wayne E. Feely
  • Patent number: 4374214
    Abstract: 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: Grant
    Filed: March 3, 1981
    Date of Patent: February 15, 1983
    Assignee: General Electric Company
    Inventors: Fred F. Holub, John T. Hoback
  • Patent number: 4370467
    Abstract: 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: Grant
    Filed: July 3, 1980
    Date of Patent: January 25, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4370465
    Abstract: 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: Grant
    Filed: December 14, 1981
    Date of Patent: January 25, 1983
    Assignee: The Dow Chemical Co.
    Inventors: Ross C. Whiteside, Jr., Adolphus V. Gist, George A. Doorakian
  • Patent number: 4369304
    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, (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: Grant
    Filed: August 5, 1980
    Date of Patent: January 18, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Nobuyuki Ikeguchi
  • Patent number: 4369302
    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 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: Grant
    Filed: December 30, 1980
    Date of Patent: January 18, 1983
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Nobuyuki Ikeguchi, Yasunori Osaki
  • Patent number: 4368317
    Abstract: 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: Grant
    Filed: May 11, 1981
    Date of Patent: January 11, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Dieter Trachsler
  • Patent number: 4366302
    Abstract: 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: Grant
    Filed: June 15, 1981
    Date of Patent: December 28, 1982
    Assignee: Lord Corporation
    Inventors: Raj N. Gounder, John T. Geary
  • Patent number: 4360655
    Abstract: 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: Grant
    Filed: June 1, 1981
    Date of Patent: November 23, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4358571
    Abstract: 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: Grant
    Filed: March 10, 1981
    Date of Patent: November 9, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Marvin L. Kaufman, George F. Salathe
  • Patent number: 4355058
    Abstract: 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: Grant
    Filed: August 14, 1978
    Date of Patent: October 19, 1982
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventors: Rainer Gras, Johann Obendorf, Elmar Wolf
  • Patent number: 4350804
    Abstract: 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: Grant
    Filed: November 21, 1980
    Date of Patent: September 21, 1982
    Assignee: PPG Industries, Inc.
    Inventors: John S. Ostrowski, John F. Grunewalder, Nicholas T. Castellucci
  • Patent number: 4350781
    Abstract: 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: Grant
    Filed: July 24, 1981
    Date of Patent: September 21, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Gerhard Grogler, Holger Meyborg
  • 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: 4341693
    Abstract: 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: Grant
    Filed: June 15, 1981
    Date of Patent: July 27, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Lothar Buxbaum
  • Patent number: 4340715
    Abstract: 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: Grant
    Filed: May 26, 1981
    Date of Patent: July 20, 1982
    Assignee: Lord Corporation
    Inventors: Raj N. Gounder, John T. Geary