Phenolic Reactant Contains At Least One Nitrogen, Phosphorus, Or Sulfur Atom Patents (Class 528/99)
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Patent number: 5237021Abstract: A thermosetting resinous composition contains (a) a polyfunctional oxazolidinone compound and (b) a polyamine which react with one another a polyurea polymer upon heating without emitting any emanating by-product. A novel class of polyfunctional oxazolidinone compounds and an improved method for producing the same are also disclosed.Type: GrantFiled: September 4, 1992Date of Patent: August 17, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Toshiyuki Ishii, Hiroyuki Nojiri, Mitsuo Yamada, Ryuzo Mizuguchi
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Patent number: 5235008Abstract: Polymer modified adducts are prepared by (A) reacting (1) an epoxy resin having an average of more than one vicinal epoxide group with (2) a compound containing an average of two or more hydrogen atoms reactive with an epoxide group; and (B) partially vinylizing reacting the product from step (A); and (C) polymerizing the partially vinylized product from step (B) with (3) a polymerizable ethylenically unsaturated monomer; with the proviso that at least one of the components (1), (2) or (3) contain one or more rodlike mesogenic moieties. These adducts are useful as epoxy resin curing agents.Type: GrantFiled: August 3, 1990Date of Patent: August 10, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5235006Abstract: Novel mesogens, epoxy resins and the synthesis thereof as well as coating binders for coating compositions based upon the mesogens and epoxy resins are described.Type: GrantFiled: September 18, 1990Date of Patent: August 10, 1993Assignee: North Dakota State UniversityInventors: Frank N. Jones, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian, Daozhang Wang
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Patent number: 5227452Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: June 29, 1992Date of Patent: July 13, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5218062Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: June 29, 1992Date of Patent: June 8, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5218061Abstract: The present invention relates to a novel polyfunctional epoxy resin having two phenolic glycidyl ether groups, one or more of alcoholic glycidyl ether groups and one or more of alcoholic hydroxyl groups in one molecules. The present invention further provides an epoxy resin composition comprising the epoxy resin. The cured product obtained from the epoxy resin composition according to the present invention is excellent in heat resistance, toughness, adhesion property and water proofness, and it is extremely useful for a wide range of application uses such as molding materials, casting materials, laminate materials, coating materials, adhesives and photoresists.Type: GrantFiled: September 10, 1991Date of Patent: June 8, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshitaka Kajiwara, Shoushi Takahashi, Kenichi Mizoguchi, Sumio Saito
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Patent number: 5218075Abstract: Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having aromatic ether repeating units in their backbones and pendent hydroxyl moieties and pendent amido, N-substituted amido and/or hydroxyalkyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol A with dihydric phenols having pendent amido, N-substituted amido and/or hydroxyalkyl moieties such as 2,2-bis(4-hydroxyphenyl)acetamide and 3,5-dihydroxybenzamide.Type: GrantFiled: February 13, 1992Date of Patent: June 8, 1993Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White, Anthony P. Haag, Shari L. Kram
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Patent number: 5218074Abstract: The invention provides epoxy resins having the following structure: ##STR1## The cross-linked epoxy resins have non-linear optical properties. The group "Z" constitutes a nonlinear optical chromophone having stilbene, azo, azomethine or propargyl moieties as linking units.Type: GrantFiled: September 17, 1991Date of Patent: June 8, 1993Assignees: Siemens Aktiengesellschaft, Siemens AktiengesellschaftInventors: Jens Nordmann, Heinz Hacker
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Patent number: 5214098Abstract: Hardenable mixtures comprising(a) an epoxide resin,(b) a latent epoxide resin hardener which starts to react only at a temperature of at least 80.degree. C. (measured by DSC at a heating rate of 10.degree. C./minute),(c) an amine having at least one amine hydrogen and(d) a thiol having at least one SH group, either the amine (c) having at least two hydrogen atoms bound to one or more nitrogen atoms or the thiol (d) having at least two SH groups, and the difference between the reaction maxima in the DSC diagram at a heating rate of 10.degree. C./minutes being at least 30.degree. C., are suitable for the production of crosslinked products, especially for the production of flexible prepregs having a non-critical B stage and a very good storability.Type: GrantFiled: November 16, 1990Date of Patent: May 25, 1993Assignee: Ciba-Geigy CorporationInventors: Frans Setiabudi, Urs Gruber
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Patent number: 5213897Abstract: Curable compositions which are precursors for cured or partially cured light stabilized epoxy resins which are the product of the reaction of some or all of the epoxy groups of an epoxy resin with an N-(2,2,6,6-tetraalkyl-4-piperidinyl)amic acid hydrazide as well as the cured or partially cured reaction products thereof together with processes for their use and articles of manufacture produced thereby are disclosed.Type: GrantFiled: April 3, 1991Date of Patent: May 25, 1993Assignee: Elf Atochem North America, Inc.Inventors: Arthur L. Baron, Ronald E. MacLeay, Jennifer P. Kmiec
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Patent number: 5212264Abstract: There are disclosed substantially linear polyarylene ether sulfones having a reduced viscosity of having a reduced viscosity of ca. 0.25 to ca. 1.5 dl/g (measured in a 1% solution in DMF at 25.degree. C.) and consisting essentially of 95-99.8% by weight of segments of formula I and of 5-0.2% by weight of segments of formula IIa, formula IIb and/or formula IIc ##STR1## the percentages by weight being based on the entire polymer and the molecular weight (number average) of the segments of formula I being 6000 to ca. 60 000, if the polymer contains solely structural units of formula IIa and/or IIb, and 1000 to ca. 60 000 if the polymer contains more than 0.1% by weight of structural units of formula IIc, and R consists of the recurring structural units of formula Ia and/or of up to 99.8% by weight, based on the total polymer, of recurring structural units of formula Ib ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.10 alkenyl, phenyl or halogen, p is an integer from 0 to 4 Ar.sub.1 and Ar.Type: GrantFiled: March 16, 1992Date of Patent: May 18, 1993Assignee: Ciba-Geigy CorporationInventors: Kurt Hoffmann, Thomas Kainmuller, Rudolf Pfaendner
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Patent number: 5202407Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorus atom per molecule.Type: GrantFiled: January 24, 1992Date of Patent: April 13, 1993Assignee: The Dow Chemical CompanyInventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
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Patent number: 5200475Abstract: A lightly-crosslinked thermosettable formulation comprises (a) a diepoxy resin, (b) an aromatic diamine of the structural formula ##STR1## in which each R is a divalent linking moiety selected from C.sub.1-6 alkylene, --S-- and --O--, and R' is ethyl, (c) an amine or phenolic crosslinking agent, and (d) 2,6-dialkyl aniline. The formulation exhibits relatively long outlife and can be used as the matrix resin in aerospace composites applications.Type: GrantFiled: June 3, 1991Date of Patent: April 6, 1993Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 5191033Abstract: The invention is an epoxy resin composition. Diol initiators are reacted with alkylene oxide and 1 to 5 wt % epoxy resin. The epoxy resin is added internally, along the length of the diol chain to yield a modified polyol of molecular weight 2000 to 5000. The modified polyol is subjected to reductive amination to yield a polyamine. This polyamine is mixed with an epoxy base resin and cured to product epoxy resins demonstrating improved strength and adhesion.Type: GrantFiled: May 11, 1992Date of Patent: March 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza, Kathy B. Sellstrom
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Patent number: 5171765Abstract: This application describes a water dispersible polymeric vehicle comprising epoxy polymers having about 5 to 50 weight percent mesogens or a cross-linkable blend of an amine salt of a mesogenic carboxylic acid, cross-linker resin and an epoxy polymer, the mesogenic acid providing about 5 to 50 weight percent mesogenic groups to the blend.Type: GrantFiled: May 8, 1991Date of Patent: December 15, 1992Assignee: North Dakota State UniversityInventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
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Patent number: 5164472Abstract: Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having backbone repeating units of m-phenylene, p-phenylene, carbonyldiphenylene and/or sulfonyldiphenyl and pendent hydroxyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol A with resorcinol.Type: GrantFiled: January 18, 1990Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, James W. Ringer
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Patent number: 5164464Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5155198Abstract: A primer composition which contains a diluent and a film forming binder wherein the film forming binder contains a siloxane condensation catalyst, an amine hardner, a silane coupling agent and the reaction product of a polydiorganosiloxane having a reactive end group and an epoxy functional phosphate ester compound. The composition is useable as a primer on aluminum substrate.Type: GrantFiled: June 14, 1991Date of Patent: October 13, 1992Assignee: Cape Cod ResearchInventor: Francis L. Keohan
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Patent number: 5151471Abstract: Epoxy resin formulations having improved storage stability comprising epoxys selected from the group consisting of polyglcidyl ethers of polycyclic bridged hydroxy-substituted polyaromatic compounds and N,N,N',N'-tetraglycidyl-bis(4-amino-3-ethylphenyl) methane with from about 6 to about 150 pbw, per hundred parts by weight of the epoxy resin components, of a solid aromatic diamine hardener insoluble in said composition at room temperature in an amount effective to cure said epoxy resin.Type: GrantFiled: October 23, 1990Date of Patent: September 29, 1992Assignee: Amoco CorporationInventors: Shahid P. Qureshi, Hugh C. Gardner
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Patent number: 5149768Abstract: Hydroxy-functional poly(ether sulfonamides) prepared by polymerizing an N,N'-dialkyl or N,N'-diaryldisulfonamide with a diepoxide in the presence of a suitable catalyst exhibit high barrier properties. These are suitable for use in the manufacture of articles such as rigid containers and flexible films exhibiting high barrier to oxygen.Type: GrantFiled: June 21, 1991Date of Patent: September 22, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, Anthony P. Haag, R. Garth Pews
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Patent number: 5143998Abstract: Hydroxy-functional poly(amide-ethers) are fabricated into articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in both dry and moist environments. For example, a polymer prepared by reacting the diglycidyl ether of 4,4'-isopropylidene bisphenol with .alpha.,.alpha.'-bis(4-hydroxybenzamido)-1,3-xylene exhibits especially high barrier.Type: GrantFiled: September 13, 1991Date of Patent: September 1, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Anthony P. Haag, Jerry E. White
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Patent number: 5134218Abstract: Poly(hydroxy amide ethers) which exhibit high barrier properties are prepared by contacting one or more amide-containing bisphenols and an epihalohydrin. These polymers are suitable for use in the manufacture of articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in moist environments.Type: GrantFiled: June 6, 1991Date of Patent: July 28, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White
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Patent number: 5128425Abstract: An epoxy resin composition for use in carbon fiber reinforced plastics which comprises the following components (A), (B), (C), and (D):(A) an epoxy resin of the bisphenol A diglycidyl ether type;(B) at least one compound selected from the group consisting of dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipyldihydrazide, azelayldihydrazide, and isophthalic acid dihydrazide;(C) a compound represented by general formula (I) ##STR1## wherein X.sub.1 and X.sub.Type: GrantFiled: June 19, 1990Date of Patent: July 7, 1992Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Yoshinobu Shiraishi, Hisashi Tada
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Patent number: 5120817Abstract: An epoxy resin composition comprises an vicinal polyepoxide and a Mannich condensation reaction product curing agent. The curing agent is the Mannich condensation reaction product of a phenol, formaldehyde and a polyoxyethylenediamine of the formula:NH.sub.2 (CH.sub.2 CH.sub.2 O).sub.x --CH.sub.2 CH.sub.2 NH.sub.2,and wherein: x ranges from 1 to 3. These epoxy resin compositions are useful in coatings, adhesives, encapsulations and composite matrices.Type: GrantFiled: February 27, 1991Date of Patent: June 9, 1992Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Harold G. Waddill, Jiang-Jen Lin
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Patent number: 5115075Abstract: Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having aromatic ether repeating units in their backbones and pendent hydroxyl moieties and pendent amido, N-substituted amido and/or hydroxyalkyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as diglycidyl ether of bisphenol A with dihydric phenols having pendent amido, N-substituted amido and/or hydroxyalkyl moieties such as 2,2-bis(4-hydroxyphenyl)acetamide and 3,5-dihydroxybenzamide.Type: GrantFiled: May 8, 1990Date of Patent: May 19, 1992Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White, Anthony P. Haag, Shari L. Kram
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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: 5098986Abstract: Normally liquid polyfunctional final Mannich condensates that are useful as curing agents for epoxy resins are prepared by reacting a para C.sub.1 -C.sub.15 alkyl phenol with formaldehyde and a first polyoxyalkylene diamine to form an intermediate Mannich condensate that is reacted, in turn, with formaldehyde and a second polyoxyalkylene diamine to form the final Mannich condensate, the first polyoxyalkylene diamine having the formula: ##STR1## wherein: n represents a positive number having a value of 1 to about 6, andR' independently represents hydrogen or a methyl group, the second polyoxyalkylene diamine having the formula: ##STR2## wherein n and n' represent positive numbers having a value of 1 to about 6,R' independently represents hydrogen or a methyl group, andR"' represents an alkyl group containing 1 to 4 carbon atoms or a cyanoethyl group.Type: GrantFiled: November 19, 1990Date of Patent: March 24, 1992Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Jiang-Jen Lin
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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: 5089588Abstract: Hydroxy-functional poly(amide-ethers) are fabricated into articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in both dry and moist environments. For example, a polymer prepared by reacting the diglycidyl ether of 4,4'-biphenol with N,N'-bis(m-hydroxyphenyl)-adipamide exhibits especially high barrier.Type: GrantFiled: February 26, 1991Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, David J. Brennan, Steven Pikulin
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Patent number: 5087688Abstract: A fibrous composite structure impregnated with a solvent-free, curable epoxy resin matrix and comprising(a) a liquid epoxy resin or a liquid mixture of epoxy resins,(b) a liquid .beta.-hydroxyamine of formula I ##STR1## wherein X is phenyl or the radical R--O--CH.sub.2 --, wherein R is an alkyl group of 4 to 20 carbons or is phenyl or phenyl which is substituted by one or more C.sub.1 -C.sub.4 alkyl groups, a liquid mixture of .beta.-hydroxyamines of formula I or a liquid mixture of one more .beta.-hydroxyamines of formula I and of a primary monomaine different from formula I or of a primary or secondary diamine, and optionally(c) a catalytically curing tertiary amine,is virtually odourless, can be stored for several days at room temperature, and has good processing properties.Type: GrantFiled: June 20, 1990Date of Patent: February 11, 1992Assignee: Ciba-Geigy CorporationInventors: Urs Gruber, Friedrich Stockinger, Elvio Manso
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Patent number: 5077379Abstract: A curable coating composition which comprisesa) a condensation polymer in which the backbone contains activated unsaturated groupings.b) a compound containing at least three blocked primary amino groupsc) a cyclic ketone of formula ##STR1## in which R.sup.1 to R.sup.6 are any non-interfering groups.Type: GrantFiled: September 22, 1989Date of Patent: December 31, 1991Assignee: ICI PLCInventor: Peter D. Palasz
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Patent number: 5075411Abstract: A curable epoxy resin composition comprises (I) an epoxy resin and (II) a curing agent. It may comprise (III) another curing agent. It is preferable for it to comprise 25 to 95 wt.% of (I) and 5 to 45 wt.% of (II).1 an epoxy resin (I) represented by the general formula: ##STR1## wherein Z represents a group selected from among a hydrogen atom, a methyl group and an ethyl group, R represents a group selected from among a hydrogen atom and alkyl groups, and n represents a number of 0 to 1.6, and2 a curing agent comprising a polyamine reaction composition (II) obtained by reacting 1 mol of a phenol (II-1) having at least one unsubstituted reactive site in the aromatic nucleus with at least 1 mol of an aliphatic polyamine (II-2) and at least 1 mol of a carbonyl compound (II-3) having at least one carbonyl group in the molecule.Type: GrantFiled: February 16, 1990Date of Patent: December 24, 1991Assignees: Nissan Motor Co., Tsuchiya Mfg. Co., Ltd., Asahi Denka Kogyo K.K., A.C.R. Co., Ltd.Inventors: Akio Ogawa, Yukio Ohsaki, Takeichiro Takehara, Tadashi Ashida, Seiichiro Hashimoto
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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: 5066735Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 5066764Abstract: This invention relates to ditertiary-butyl substituted bridged di(cyclohexylamines) where the tert-butyl substituent is alpha to the amine group and to polyepoxide formulations incorporating the di(cyclohexylamine). The formula of the diamine is: ##STR1## wherein R is tert-butyl. The di(tertiary butyl)methylene bridged cyclohexylamines have delayed reactivity when incorporated in epoxy resins and they also enhance physical properties in high resilience polyurethane foams.Type: GrantFiled: June 26, 1990Date of Patent: November 19, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Peter A. Lucas, Menas S. Vratsanos
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Patent number: 5057557Abstract: Epoxy resins are modified by reaction with an acidified polytertiary amine-containing compound. These modified epoxy resins when cured result in products having improved properties.Type: GrantFiled: May 11, 1990Date of Patent: October 15, 1991Assignee: The Dow Chemical CompanyInventors: Duane S. Treybig, Pong S. Sheih, John M. McIntyre
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Patent number: 5057556Abstract: A non-gelled amine-epoxide reaction product and acid addition salts thereof where the product is obtained by co-reacting;a) a secondary amine NHR.sup.1 R.sup.2, wherein R.sup.1 and R.sup.2 the same or different are C.sub.2 or C.sub.3 hydroxyalkyl groups,b) a polyepoxide,c) optionally a polyoxyalkylene polyamine,d) a product of the reaction between an epoxide with at least two epoxy groups and which contains less than 40% by weight of aromatic groups, and an amine of formula (1):NR.sup.3 R.sup.4 (CH.sub.2)n NH.sub.2 (1)in which n is from 2 to 6, and where R.sup.3 and R.sup.4, the same or different are methyl or ethyl, and optionally,e) a monoepoxidethe components of product (D) being chosen so that the non-gelled amine epxoide reaction product is a liquid at temperature above -5.degree. C.Type: GrantFiled: October 23, 1989Date of Patent: October 15, 1991Assignee: Imperial Chemical Industries PLCInventor: Richard P. Redman
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Patent number: 5053475Abstract: An epoxy resin composition characterized by comprising, as essential components,(A) a bifunctional epoxy resin,(B) a trifunctional epoxy resin,(C) a phenol compound represented by the following formula ##STR1## (X.sub.1 to X.sub.8 each represent Br, Cl or H and at least four of X.sub.1 to X.sub.8 each represent Br or Cl; R.sub.1 and R.sub.2 each represent H or CH.sub.3), and(D) 4,4'-diaminodiphenyl sulfone or 3,3'-diaminodiphenyl sulfone.Type: GrantFiled: June 22, 1990Date of Patent: October 1, 1991Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hisashi Tada, Akira Agata, Masahiro Saruta, Takashi Murata, Takatoshi Kubo
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Patent number: 5043411Abstract: The present invention generally relates to a thermosettable cyanate ester resin composition which contains a fortifier that is the reaction product of an epoxy and an aromatic reactant selected from an aromatic amine and an aromatic amide. Thermoset cyanate ester resin compositions of the present invention have improved flexural strength and/or flexural modulus. The compositions of the present invention may be used to prepare circuit boards or molded parts.Type: GrantFiled: May 14, 1990Date of Patent: August 27, 1991Assignee: Nova Petrochemicals Inc.Inventors: Kam W. Ho, Adrian Cassola
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Patent number: 5039777Abstract: An aniline-resorcin-formaldehyde copolycondensation product having a particular mol ratio of aniline to resorcin is used in an adhesive composition for well adhering fibrous material to rubber.Type: GrantFiled: January 23, 1991Date of Patent: August 13, 1991Assignee: Bridgestone CorporationInventors: Toshihiro Yotsumoto, Koichi Morita, Takeshi Kinoshita
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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: 5019639Abstract: Advanced epoxy resins are disclosed which can be obtained by reacting liquid or semi-solid aromatic opoxy resins with aliphatic diols, and subsequently reacting the reaction product with mono- or binuclear bisphenols in the presence of a cyclic quaternary ammonium salt.Type: GrantFiled: April 2, 1990Date of Patent: May 28, 1991Assignee: Ciba-Geigy CorporationInventors: Arnold Hofer, Alex Wegmann
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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: 5001213Abstract: Novel thermosetting resin compositions comprise a mixture of the epoxyalkylether of a 1,6-diazo[4.4]spirodilactam having a hydroxyaryl substituent on each of the spiro ring nitrogen atoms, and at least one amine compound. The cured compositions obtained by heating the resin compositions to an elevated temperature have relatively high glass transition temperatures and good physical properties.Type: GrantFiled: February 5, 1990Date of Patent: March 19, 1991Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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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: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4957995Abstract: A low viscosity epoxy resin, i.e., a low viscosity polyglycidyl derivative, of an aminophenol having at least one alkyl group on its aromatic ring of which viscosity is 15 poises or below as measured at 25.degree. C., a resin composition containing said resin, and a fiberreinforced composite material containing as matrix a cured product of said epoxy resin composition and a fiber as reinforcing material.Type: GrantFiled: September 5, 1989Date of Patent: September 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii
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Patent number: 4956440Abstract: Polymeric tertiary arylamine compounds of the phenoxy resin type which find utility especially in electrophotographic imaging.Type: GrantFiled: November 23, 1988Date of Patent: September 11, 1990Assignee: Xerox CorporationInventors: William W. Limburg, Dale S. Renfer, John F. Yanus, Leon A. Teuscher
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Patent number: 4954584Abstract: Thermosetting resin compositions comprise a mixture of a 1-arylcyclobutenecarboxylate ester of a glycidyloxy compound having at least two glycidyloxy substituents and at least one polymerizable monomer having at least two substituents with multiple valence bonds between adjacent atoms. Also claimed are the cured products obtained by heating such compositions.Type: GrantFiled: June 12, 1989Date of Patent: September 4, 1990Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 4954583Abstract: Novel 1-arylcyclobutenecarboxylate esters of glycidyloxy compounds having at least two glycidyloxy substituents are self-curing thermoset resins. The cured products derived by applying heat to the esters are crosslinked insoluble solids having good properties.Type: GrantFiled: June 12, 1989Date of Patent: September 4, 1990Assignee: Shell Oil CompanyInventor: Pen-Chung Wang