Two Or More Nitrogen-containing Reactants Patents (Class 528/120)
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Patent number: 5270406Abstract: Advanced epoxy resin compositions are prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties. Curable compositions containing these advanced epoxy resin compositions are useful in adhesives, coatings, laminates castings and the like.Type: GrantFiled: September 15, 1992Date of Patent: December 14, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
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Patent number: 5266365Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.Type: GrantFiled: February 28, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical CompanyInventors: John J. Kester, H. Craig Silvis
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Patent number: 5266405Abstract: This invention relates to thermosetting compositions for the production of epoxide networks of very high impact strength, to a process for their preparation and to their use as polymer materials, coating compounds, adhesives and materials for electrical insulation.Type: GrantFiled: July 22, 1991Date of Patent: November 30, 1993Assignee: Bayer AktiengesellschaftInventors: Stephan Kirchmeyer, Hanns P. Muller, Alexander Karbach, Joachim Franke
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Patent number: 5266661Abstract: Curable compositions are disclosed which contain (I) an advanced resin composition prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties and (II) a suitable curing agent.Type: GrantFiled: September 15, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
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Patent number: 5212261Abstract: Latent, heat-curable epoxy resin compositions containing metal carboxylate curing systems provide exceptional latency, particularly at elevated temperature, as well as facile curing, high T.sub.g and adhesive strength, and other attractive properties. The metal carboxylates comprise alkali metals and alkaline earth metals, aromatic and aliphatic metal carboxylates. The preferred curing systems comprise synergistic combinations of the metal carboxylates with cure modifiers.Type: GrantFiled: December 17, 1990Date of Patent: May 18, 1993Assignee: Henkel Research CorporationInventor: Thomas J. Stierman
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Patent number: 5200494Abstract: A one-pack type epoxide composition which has excellent storage stability and which can be rapidly cured at relatively low temperature is provided. It comprises as effective components (A) at least one epoxide having more than one, preferably more than 1.5 epoxy groups per a molecule, and (B) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (c) at least one diisocyanate, or (C) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (d) at least one epoxide having one or more epoxy groups in a molecule, and (c) at least on diisocyanate.Type: GrantFiled: April 10, 1991Date of Patent: April 6, 1993Assignee: Fuji Kasei Kogyo Co., Ltd.Inventors: Masao Kubota, Ritaro Nagabuchi, Yasuo Chiba
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Patent number: 5162438Abstract: In an adhesive for printed circuit boards, whose main components are an epoxy resin and a polymer rubber, the improvement wherein the polymer rubber is a hydrogenated conjugated diene polymer rubber having not more than 100 ppm of metal content, not more than 100 ppm of ion content as determined by ion chromatography, and an iodine value of not more than 120, the ratio by weight of the hydrogenated conjugated diene polymer rubber to the epoxy resin in the adhesive being 35-75 weight % to 65-25 weight %.Type: GrantFiled: August 27, 1991Date of Patent: November 10, 1992Assignee: Nippon Zeon Co., Ltd.Inventor: Suguru Tsuji
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Patent number: 5162439Abstract: In an adhesive for printed circuit boards, whose main components are an epoxy resin and a polymer rubber, the improvement wherein the polymer rubber is a hydrogenated conjugated diene polymer rubber having not more than 100 ppm of metal content, not more than 100 ppm of ion content as determined by ion chromatography, and an iodine value of not more than 120.Type: GrantFiled: November 17, 1989Date of Patent: November 10, 1992Assignee: Nippon Zeon Co., Ltd.Inventor: Suguru Tsuji
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Patent number: 5147905Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.Type: GrantFiled: May 1, 1991Date of Patent: September 15, 1992Assignee: The Dow Chemical CompanyInventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
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Patent number: 5140068Abstract: Curable epoxy resins are toughened with statistical monofunctional carboxyl, amine or epoxy terminated reactive polymers and have low viscosities before cure thereby making them useful in a wide range of applications. The cured epoxy resin systems which are modified by the statistical monofunctional reactive polymers have physical properties, such as adhesion and elongation, generally equal to or better than those of cured epoxy resin systems modified with statistical difunctional reactive polymers. A process of preparation for the modified epoxy resin systems of the present invention includes admixing an epoxy resin with a statistical monofunctional carboxyl, amine, or epoxy-terminated reactive polymer in the presence of a curing agent and reaction therewith to form the toughened, cured epoxy resin system.Type: GrantFiled: March 22, 1991Date of Patent: August 18, 1992Assignee: The B. F. Goodrich CompanyInventors: Alan R. Siebert, Robert J. Bertsch
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Patent number: 5138018Abstract: A one-pack type epoxy resin composition which can be easily handled and has excellent curing characteristics is provided by blending at least one epoxy resin having more than one epoxy groups in a molecule with a curing agent obtained by reacting at least one diamine compound, at least one N,N-dialkylaminoalkylamine, at least one epoxy resin having more than one epoxy groups in a molecule, urea, and as an optional component, at least one monoamine compound.Type: GrantFiled: December 3, 1990Date of Patent: August 11, 1992Assignee: Fuji Kasei Kogyo Co. Ltd.Inventors: Kijuro Tashiro, Ritaro Nagabuchi
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Patent number: 5128059Abstract: Blends of diaminoisopropylbenzene (DAIBP) and diaminoethylbenzene (DAEB) are provided for curing epoxy resins. The cured epoxy resins have increased tensile strength and slightly lower glass transition temperatures as compared with resins cured with either diamine alone.Type: GrantFiled: September 13, 1991Date of Patent: July 7, 1992Assignees: First Chemical Corporation, The University of Southern MississippiInventors: Robson F. Storey, Arthur C. Bayer, Sudhakar Dantiki
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Patent number: 5112934Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.Type: GrantFiled: November 27, 1989Date of Patent: May 12, 1992Assignee: The Dow Chemical CompanyInventors: John J. Kester, H. Craig Silvis
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Patent number: 5108575Abstract: Disclosed herein is a cathodic electrodepositable resin containing polyamine enamine. It has been discovered that reacting epoxy resins with polyamine enamine is a viable method of introducing amine functionality to the epoxy resin. The polyamine enamine route results in the desired high pH and stable dispersion in the electrocoat bath.Type: GrantFiled: August 8, 1990Date of Patent: April 28, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Tapan K. Debroy
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Patent number: 5093458Abstract: 4-Methyl-2-morpholinone is an excellent catalytic curing agent for epoxy resins. The compound is also an accelerator when combined with standard epoxy resin curing agents.Type: GrantFiled: December 17, 1990Date of Patent: March 3, 1992Assignee: Texaco Chemical CompanyInventors: Harold G. Waddill, Wei-Yang Su
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Patent number: 5093459Abstract: Solid, fusible bismaleimide resins formed from a mixture of a bismaleimide and an aminophenol still contain from 70 to 90 mol % of unconverted bismaleimide and from 30 to 60 mol % of unconverted aminophenol.Type: GrantFiled: July 9, 1990Date of Patent: March 3, 1992Assignee: BASF AktiengesellschaftInventors: Roland Peter, Philipp Eisenbarth, Lothar Schlemmer
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Patent number: 5091474Abstract: A two component-type curing agent composition is disclosed which comprises a first curing agent which is capable of cross-linking an epoxy resin and which is at least one member selected from primary amines, phenolic compounds and acid anhydrides, and a second curing agent which is at least one compounds represented by the following general formula: ##STR1## wherein X is --CR.sub.1 R.sub.2 --, --CO--, --COO--, --SO.sub.2 --, --SO--, --S--, --O--, --NR.sub.1 --, --SiR.sub.1 R.sub.2 -- or --POR.sub.1 -- where R.sub.1 and R.sub.2 each stands for hydrogen, a lower alkyl or a phenyl; Y and Y' each stands for hydrogen, a lower alkyl or an electron attracting group; R is a lower alkyl; and m and n each is an integer of 1-4.Type: GrantFiled: January 18, 1991Date of Patent: February 25, 1992Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Shinkichi Murakami, Osamu Watanabe, Sadahisa Wada, Makoto Miyazaki, Hiroshi Inoue
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Patent number: 5075379Abstract: The use of a blend of diaminoisopropylbenzene (DAIPB) and an amine terminated butadiene nitrile liquid rubber (ATBN) for curing epoxy resins is provided. The DAIPB/ATBN blend produces a rubber toughened epoxy resin having improved tensile properties.Type: GrantFiled: September 10, 1990Date of Patent: December 24, 1991Assignees: First Chemical Corporation, The University of Southern MississippiInventors: Robson F. Storey, Sudhakar Dantiki, J. Patrick Adams
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Patent number: 5070159Abstract: Addition compounds which are suitable as dispersants for solids in organic media are obtained from polyepoxides based on novolaks having 3 to 11 nuclei and a mixture of aliphatic, aromatic and/or heterocyclic amines.Type: GrantFiled: June 16, 1989Date of Patent: December 3, 1991Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Andreas Sommer, Adolf Kroh, Jurgen Hohn, Otmar Hafner, Wolfgang Rieper
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Patent number: 5049639Abstract: Blends of diaminoisopropylbenzene (DAIPB) and diaminoethylbenzene (DAEB) are provided for curing epoxy resins. The cured epoxy resins have increased tensile strength and slightly lower glass transistion temperatures as compared with resins cured with either diamine alone.Type: GrantFiled: February 23, 1989Date of Patent: September 17, 1991Assignees: First Chemical Corporation, The University of Southern MississippiInventors: Robson F. Storey, Arthur C. Bayer, Sudhakar Dantiki
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Patent number: 5039720Abstract: An aqueous electrophoretic coating material, which can be deposited at the cathode and contains(A) 90 to 50% by weight, based on the total portion of synthetic resin vehicle, of one or several polycondensation, polymerization and/or poly-addition resins, the resin or, in the event that several resins are present, their mixture(a) having a number average molecular weight (Mn) of 700 to 10,000(b) having 1.2.times.10.sup.23 to 21.7.times.10.sup.23 lateral or terminal double bonds per 1,000 g, corresponding to a hydrogenation iodine number of 5 to 90,(c) optionally containing primary and/or secondary hydroxyl groups, corresponding to a hydroxyl number of 0 to 450 mg KOH/g of resin, and(d) tertiary amino groups corresponding to an amine number of 30 to 450 mg KOH/g of resin.Type: GrantFiled: September 30, 1988Date of Patent: August 13, 1991Assignee: Hoechst AktiengesellschaftInventors: Dietrich Saatweber, Georg Hendriux, Gerhard Brindopke, Helmut Plum
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Patent number: 5034434Abstract: Non-gelled amine-epoxide reaction products are obtained by co-reacting a secondary amine, a polyoxyalkylene polyamine, a polyepoxide and a monoepoxide. The products are cross-linkable and are useful in aqueous coating compositions, particularly when applied to a substrate by cathodic electrodeposition.Type: GrantFiled: October 18, 1989Date of Patent: July 23, 1991Assignee: Imperial Chemical Industries PLCInventors: Michael Beresford, Richard P. Redman
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Patent number: 5026743Abstract: Non-gelled amine-epoxide reaction products are obtained by co-reacting a secondary amine, a polyoxyalkylene polyamine, a polyepoxide and optionally a monoepoxide. The products are crosslinkable and are useful in aqueous coating compositions, particularly when applied to a substrate by cathodic electrodeposition.Type: GrantFiled: October 18, 1989Date of Patent: June 25, 1991Assignee: Imperial Chemical Industries PLCInventors: Michael P. Beresford, Richard P. Redman
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Patent number: 5025067Abstract: An epoxy resin comprising an active hydrogen compound having at least three active hydrogen atoms capable of reacting with an epoxy group in its molecule or butadine or isoprene as a main monomer is modified with an oligomer having on average at least 1.5 equivalents of active hydrogen capable of reacting with an epoxy group in its molecule. An epoxy resin modified with a bisphenol and a compound having active hydrogen or acid anhydride groups capable of reacting with an epoxy group is also provided. A toner containing the epoxy resin as a binder is useful in electrostatography.Type: GrantFiled: November 16, 1988Date of Patent: June 18, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yohzoh Yamamoto, Goro Suzuki, Hideo Nakamura, Kiyomi Yasuda
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Patent number: 5025078Abstract: This invention relates to polyepoxide resins cured with an amine composition containing 1-methyl-2,6-cyclohexanediamine. The resulting polyepoxide resins generally are more easily processable and have improved thermal stability, greater elongation and enhanced fracture toughness.Type: GrantFiled: February 2, 1990Date of Patent: June 18, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Peter A. Lucas, Jeremiah P. Casey
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Patent number: 5017674Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ether or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.Type: GrantFiled: June 27, 1990Date of Patent: May 21, 1991Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsuga Hayashi
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Patent number: 5015718Abstract: A thermosetting mixture for use as an adhesive, as well as other applications, that is substantially nonmutagenic. This mixture is based upon a thermosetting resin selected from polyurethane and epoxy resins, using an improved curing agent that does not contain mutagenic components. Specifically, the curing agent is a multi-mixture of substituted alkylanilines produced by an improved process. These alkylanilines are formed by condensation of at least two 2,6-dialkylanilines with a formaldehyde in an acid solution. Upon purification, at least three aromatic diamines are formed that are used for the curing agent with the polyurethane and epoxy resisn. Pot life, green strength and ultimate strength are comparable to adhesives of the prior art that contain mutagenic constituents. Although several dianilines are described, the preferred curing agents are formed using 2,6-diethylaniline (DEA) and 2,6-diisopropylaniline (DIPA), where the mole % of DEA and DIPA is 38-48 and 62-52, respectively.Type: GrantFiled: June 30, 1989Date of Patent: May 14, 1991Assignee: Martin Marietta Energy Systems, Inc.Inventor: George F. Dorsey
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Patent number: 5015673Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.Type: GrantFiled: May 25, 1990Date of Patent: May 14, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
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Patent number: 5015672Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.Type: GrantFiled: May 25, 1990Date of Patent: May 14, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
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Patent number: 4996279Abstract: Dissymmetric new epoxy polymer materials have improved processability because they can be cured at lower temperatures.Type: GrantFiled: October 7, 1988Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4980398Abstract: Disclosed herein is a cathodic electrodepositable resin containing polyamine enamine. It has been discovered that reacting epoxy resins with polyamine enamine is a viable method of introducing amine functionality to the epoxy resin. The polyamine enamine route results in the desired high pH and stable dispersion in the electrocoat bath.Type: GrantFiled: February 23, 1990Date of Patent: December 25, 1990Assignee: E. I. du Pont de Nemours and CompanyInventors: Ding Y. Chung, Tapan K. Debroy
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Patent number: 4956402Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 200 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amimo group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.Type: GrantFiled: June 23, 1988Date of Patent: September 11, 1990Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
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Patent number: 4956411Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ester or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.Type: GrantFiled: January 30, 1989Date of Patent: September 11, 1990Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsugu Hayashi
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Patent number: 4931496Abstract: Fiber-reinforced compositions comprising a structural fiber and a cyanate ester resin formulation having an N-substituted urea compound as a latent cure accelerator provide rapid-curing prepreg with good out-time characteristics. The prepreg may be used to form composite articles with good toughness and excellent retention of properties on extended exposure to moisture at elevated temperatures.Type: GrantFiled: March 24, 1989Date of Patent: June 5, 1990Assignee: Amoco CorporationInventors: Shahid P. Qureshi, Hugh C. Gardner, Richard H. Newman-Evans
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Patent number: 4929650Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki KaishaInventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
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Patent number: 4918157Abstract: Urea compounds having a plurality of substituents selected from hydrogen, substituted hydrocarbyl radicals and unsubstituted hydrocarbyl radicals are good latent cure accelerators for thermosetting cyanate resin formulations. The resulting cyanate resin formulations are useful as coatings, adhesives and as impregnating resins, particularly in applications where extended storage at or near room temperature is desired.Type: GrantFiled: September 28, 1988Date of Patent: April 17, 1990Assignee: Amoco CorporationInventors: Hugh C. Gardner, Richard H. Newman-Evans
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Patent number: 4874833Abstract: A curable epoxy resin composition comprising(a) a low viscosity liquid epoxy resin;(b) an alkyl hindered aromatic primary diamine curing agent having at least two aromatic rings;(c) a trialkylsulfonium salt amine cure accelerator; and(d) a liquid monoaromatic primary amine curing agent;(e) at least one reactive monomer; and(f) a peroxide polymerization initiator.Type: GrantFiled: August 22, 1988Date of Patent: October 17, 1989Assignee: Shell Oil CompanyInventor: Jacqueline A. Kershaw
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Patent number: 4775736Abstract: Epoxy resins having acceptable pot lives, degrees of reactivity, and physical properties are obtained by the use of curing agent compositions which comprise about 99.6-90% by weight of a hindered aromatic diamine, such as diethyltoluenediamine, and about 0.4-10% by weight of an accelerator complex of boron trifluoride and a cycloaliphatic diamine, such as isophoronediamine.Type: GrantFiled: August 26, 1987Date of Patent: October 4, 1988Assignee: Ethyl CorporationInventor: Paul L. Wiggins
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Patent number: 4766196Abstract: A rapid curing epoxy resin composition comprising a mixture of(A) A first component comprising a polyepoxide and(B) A second component comprising a mixture of the novel reaction product of(1) an ammonium salt of a non-nucleophilic acid with(2) the reaction product of(a) a bicyclic amide acetal with(b) an amine, and(3) an amine curing agent, is described.Type: GrantFiled: August 14, 1987Date of Patent: August 23, 1988Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Teresa A. DeLong
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Patent number: 4764579Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.Type: GrantFiled: July 7, 1987Date of Patent: August 16, 1988Assignee: The Oakland CorporationInventor: Richard B. Wallace
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Patent number: 4740568Abstract: A poly(triazolinethione) is prepared by a process comprising the steps:(a) providing a poly(acylthiosemicarbazide),(b) cyclodehydrating the poly(acylthiosemicarbazide) by subjecting it to an elevated temperature in the presence of an aqueous alkaline solution to form a polyanion of a poly(triazolinethione),(c) treating the polyanion of the poly(triazolinethione) with aqueous acid solution to provide the poly(triazolinethione), and(d) isolating the resulting poly(triazolinethione).Type: GrantFiled: September 3, 1986Date of Patent: April 26, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Stephen J. Cato, Jerald K. Rasmussen, Larry R. Krepski, Steven M. Heilmann
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Patent number: 4732961Abstract: A spherical particulate adhesive comprising particles of a partially amine cured epoxy resin as the main component and having an average particle size of 0.3 to 500 .mu.m, in which particles of the epoxy resin contain an at least partially compatible agent homogeneously in the interior thereof. This adhesive is a heat-curable adhesive and has a very high bonding force. After bonding, the adhesive is chemically stable and is especially preferably used for bonding in the field of electronic material, such as liquid crystal display devices, which are apt to be degraded by impurities and for which high-precision bonding is required.Type: GrantFiled: September 18, 1986Date of Patent: March 22, 1988Assignee: Toray Industries, Inc.Inventor: Koichiro Oka
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Patent number: 4714648Abstract: A prepreg obtained by impregnating fibers with an epoxy resin composition by a hot melt method is described, wherein the epoxy resin composition comprises components (A), (B), and (C), wherein(A) is an epoxy resin(B) is a hardening agent composition containing a hydrazide type hardening agent for an epoxy resin, and having a melting point of not higher than 160.degree. C., and (B) further contains at least one compound selected from the group consisting of alcohols and phenols having a melting point of not less than 50.degree. C.,(C) is a urea compound represented by the formula ##STR1## wherein X and Y each represents H, Cl, or OCH.sub.3.Type: GrantFiled: August 1, 1985Date of Patent: December 22, 1987Assignee: Toho Rayon Co., Ltd.Inventor: Yasuhisa Nagata
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Patent number: 4705842Abstract: The present invention provides a process for hardening epoxide resin masses, wherein there is added a solution of dicyandiamide and cyanamide in a weight ratio of from 0 to 10:1 in at least one organic solvent.The present invention also provides a hardener solution for epoxide resin masses, consisting of dicyandiamide and cyanamide in a weight ratio of 0 to 10:1 and at least one organic solvent.Type: GrantFiled: March 21, 1986Date of Patent: November 10, 1987Assignee: SKW Trostberg AktiengesellschaftInventor: Joachim von Seyerl
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Patent number: 4701378Abstract: Adhesion between surfaces of metal, reinforced plastics, glass, friction material or ceramics is effected using an adhesive comprising(a) an epoxide resin(b) a nitrogen-containing latent curing agent for this resin, such as dicyandiamide, isophthalic acid dihydrazide or adipic acid dihydrazide, and(c) as accelerator for the cure, and dispersed as a powder in (a) and (b), a solid solution of a nitrogen base having a boiling point above 130.degree. C. and a phenol-aldehyde resin.Typical nitrogen bases used in (c) include benzyldimethylamine, benzimidazole and 2-methylimidazole. Typical phenolic resins are those prepared from phenol and formaldehyde.Type: GrantFiled: April 2, 1986Date of Patent: October 20, 1987Assignee: Ciba-Geigy CorporationInventors: Madan M. Bagga, Christopher H. Bull
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Patent number: 4686272Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.Type: GrantFiled: July 10, 1985Date of Patent: August 11, 1987Assignee: The Oakland CorporationInventor: Richard B. Wallace
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Patent number: 4683284Abstract: A mixture of an adhesive composition comprising (A) an epoxy resin and an oxime carbamate and (B) an amine hardener containing primary, secondary or tertiary amino or amido-amine groups and its process for curing said adhesive are described.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4670533Abstract: The invention relates to a substantially anhydrous composition containing(a) an epoxy resin,(b) as hardener for the epoxy resin, the product obtained (i) by finely homogenizing (1) dicyandiamide and (2) urea by grinding (1) and (2) together or dissolving (1) and (2) in a common solvent, or (ii) by melting (1) and (2) together or (iii) by partially reacting (1) and (2) in a common solvent, the weight ratio of (1) and (2) being in the range from 4:1 to 1:4, and, optionally,(c) a curing accelerator.The compositions are suitable in particular for the preparation of coatings, preferably as powder coating compositions, and are distinguished by a very good relationship between levelling and reactivity, and the cured coatings have excellent stability to solvents and boiling water as well as excellent mechanical properties.Type: GrantFiled: May 27, 1986Date of Patent: June 2, 1987Assignee: Giba-Geigy CorporationInventor: Horst Lauterbach
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Patent number: 4663398Abstract: Hydroxyaromatic oligomers are prepared by (I) reacting (A) an aromatic hydroxyl-containing material such as bisphenol A with (B) a cyanogen halide such as cyanogen bromide in the presence of a base such as triethylamine and (II) co-oligomerizing the cyanate-containing product from (I) with (C) a polymaleimide such as the reaction product of maleic anhydride with methylenedianiline optionally in the presence of (D) a co-oligomerization catalyst such as cobalt naphthenate. These oligomers are useful in the preparation of epoxy resins.Type: GrantFiled: February 24, 1986Date of Patent: May 5, 1987Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4652492Abstract: A curable composition which contains polyepoxide and amine curing agent free of amide groups and which is of a substantially lower viscosity than the polyepoxide is improved by thickening the amine to a viscosity comparable to that of the polyepoxide. The amine is thickened by either incorporating into the amine curing agent a polyamide in an amount not exceeding 35 percent by weight based on the amount of amine curing agent of a polyamide; or converting a portion of the amine curing agent to polyamide by in situ chain extension to form amide groups wherein the chain extension is carried out in an excess of amine curing agent before the amine curing agent is admixed with the polyepoxide component of the curable composition; or a combination thereof.Type: GrantFiled: April 11, 1985Date of Patent: March 24, 1987Assignee: PPG Industries, Inc.Inventors: Jerome A. Seiner, Raymond F. Schappert