Contains Nitrogen Atom Patents (Class 525/526)
  • Patent number: 5216093
    Abstract: The present invention discloses a low-temperature curing epoxy resin composition including: an epoxy resin main agent to which unsaturated acid ester of polyhydric alcohol is added and which contains epoxy resin having urethane bonds in the molecules thereof; and a curing agent containing an alicyclic amine compound. This epoxy resin composition may be rapidly cured even at a low temperature and presents a good work efficiency. This epoxy resin composition may be prepared as a cured body excellent in resistance to hot water, mechanical strength, impact resistance and the like.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: June 1, 1993
    Assignee: Sumitomo Rubber Industries, Ltd.
    Inventors: Shuichi Hayashi, Tetsuya Kojimoto
  • Patent number: 5214098
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: May 25, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Frans Setiabudi, Urs Gruber
  • Patent number: 5213897
    Abstract: 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: Grant
    Filed: April 3, 1991
    Date of Patent: May 25, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventors: Arthur L. Baron, Ronald E. MacLeay, Jennifer P. Kmiec
  • Patent number: 5212263
    Abstract: A powder coating composition forming a textured finish comprises epoxy resin, methylene disalicylic acid and an imidazole Bisphenol A epoxy resin.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: May 18, 1993
    Assignee: Morton International, Inc.
    Inventor: Dean A. Schreffler
  • Patent number: 5212261
    Abstract: 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: Grant
    Filed: December 17, 1990
    Date of Patent: May 18, 1993
    Assignee: Henkel Research Corporation
    Inventor: Thomas J. Stierman
  • Patent number: 5206274
    Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups is improved by using as the epoxy-based resin a blend of (I) an epoxy-based resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which diol is essentially free of ether oxygen atoms, such as a condensation product of 1,4-butanediol and epichlorohydrin, optionally (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A, (3) a dihydric phenol such as bisphenol A, and optionally (4) a capping agent such as p-nonylphenol and (II) a different cationic epoxy-based resin. Such resin blends can be utilized in cathodic electrodeposition coating systems.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: April 27, 1993
    Assignee: The Dow Chemical Company
    Inventors: Nancy A. Rao, Richard A. Hickner
  • Patent number: 5200494
    Abstract: 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: Grant
    Filed: April 10, 1991
    Date of Patent: April 6, 1993
    Assignee: Fuji Kasei Kogyo Co., Ltd.
    Inventors: Masao Kubota, Ritaro Nagabuchi, Yasuo Chiba
  • Patent number: 5191033
    Abstract: 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: Grant
    Filed: May 11, 1992
    Date of Patent: March 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza, Kathy B. Sellstrom
  • Patent number: 5189119
    Abstract: An article coated with a cationically electrodepositable paint composition comprises (A) a resin having hydroxyl and cationic groups, (B) an epoxy resin having at least 2 epoxy groups, each directly bound to an alicyclic ring, and (C) lead hydroxide and/or lead maleate as curing catalyst(s).
    Type: Grant
    Filed: October 21, 1991
    Date of Patent: February 23, 1993
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5187198
    Abstract: A resin composition for cationically electro-depositable paint comprising (A) a base resin containing a primary hydroxyl group and a cationic group and (B) a crosslinking agent, said crosslinking agent (B) being a product obtained by reacting (B-1) a compound containing in a molecule one hydroxyl group and at least one alicyclic epoxy group with (B-2) a polyisocyanate compound selected from aliphatic, alicyclic and aromatic-aliphatic polyisocyanates such that in principle, a free isocyanate group substantially does not remain.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: February 16, 1993
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5179139
    Abstract: An epoxy resin composition used as a matrix for a fiber-reinforced composite is disclosed, which comprises the following components:(A) a bifunctional epoxy resin;(B) at least one of a trifunctional epoxy resin and a tetrafunctional epoxy resin;(C) a dihydroxybiphenyl compound represented by the following general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and(D) an aromatic amine,wherein said components (A), (B), (C) and (D) are used in amounts satisfying the following conditions:1/0.1.gtoreq.a/b.gtoreq.1/1.210/1.gtoreq.(a+b)/c.gtoreq.1/11/0.8.gtoreq.(a+b-c)/d.gtoreq.1/1.5wherein a represents the molar number of epoxy groups in component (A), b represents the molar number of epoxy groups in component (B), c represents the molar number of phenolic OH groups in component (C) and d represents the molar number of NH groups in component (D).
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: January 12, 1993
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Masahiro Sugimori, Hisashi Tada, Kazuya Goto, Masahiro Saruta
  • Patent number: 5175220
    Abstract: The invention relates to new compounds of the general formulas ##STR1## where R is a divalent, optionally branched aliphatic, cyclic or alicyclic hydrocarbon group having from 2 to 10 carbon atoms; R.sup.1 and R.sup.2 are, independently of one another, hydrogen, or aliphatic or aromatic hydrocarbon groups; R.sup.3 is --COOH, --CN, --COOC.sub.2 H.sub.4 --OH, --CONH--NH.sub.2 or --COOR.sup.4 ; R.sup.4 is an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and n is 2 or 3.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: December 29, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5175219
    Abstract: The invention relates to new compounds of the general formula ##STR1## where R is a divalent, optionally branched aliphatic, cyclic or alicyclic hydrocarbon group having from 2 to 10 carbon atoms; R.sup.1 and R.sup.2 are, independently of one another, hydrogen, or aliphatic or aromatic hydrocarbon groups; R.sup.3 is --COOH, --CN, --COOC.sub.2 H.sub.4 --OH, --CONH--NH.sub.2 or --COOR.sup.4 ; R.sup.4 is an aliphatic hydrocarbon group having from 1 to 4 carbon atoms; and n is 2 or 3.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: December 29, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5171765
    Abstract: 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: Grant
    Filed: May 8, 1991
    Date of Patent: December 15, 1992
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
  • Patent number: 5155182
    Abstract: The invention relates to new imidazolyl derivatives, their use as curing agents in epoxy-resin compositions, and curable epoxy-resin compositions containing them and composed of an epoxy resin and compounds of the general formula ##STR1## where R is the group of the alcohol component used to produce the glycidyl ethers, R.sup.1 and R.sup.2 are, independently of each other, hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5, n is 2 or 3, R.sup.3 is COOH, --CH, --COHN--N.sub.H2, --COOCH.sub.2 --CH.sub.2 --OH or COOR.sup.4, R.sup.4 being an aliphatic hydrocarbon group having from 1 to 4 carbon atoms, and m is equal to the valence of R.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: October 13, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5153239
    Abstract: An epoxy resin powder coating composition having excellent thermal resistance, mechanical strength, hardening speed and storage stability which comprises an epoxy resin mixture comprising a bisphenol type epoxy resin and a polyfunctional epoxy resin having at least three epoxy groups in the molecule; a hardener comprising a mixture of dicyandiamide and a compound represented by formula (I) below, and a filler: ##STR1## wherein, R.sup.1 represents an alkyl group or an aryl group, and preferably represents a phenyl group from the view of storage stability; and R.sup.2 represents a cyanoethyl group, a vinyl group, or a phenyl group.The powder coating composition is suitably used in fixing stator coils or armature coils in motors or generators.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: October 6, 1992
    Assignee: Somar Corporation
    Inventors: Katugi Kitagawa, Akira Shinozuka
  • Patent number: 5151471
    Abstract: 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: Grant
    Filed: October 23, 1990
    Date of Patent: September 29, 1992
    Assignee: Amoco Corporation
    Inventors: Shahid P. Qureshi, Hugh C. Gardner
  • Patent number: 5147906
    Abstract: A cationically electrodepositable resin composition containing as main component primary hydroxyl group-containing cationic resin obtained by reacting epoxy resin (A) having at least three epoxy group-containing functional groups represented by the following structural formula (I) ##STR1## with primary or secondary amine compound (B) containing primary hydroxyl group and optionally, further phenol compound (C) having at least one phenolic hydroxyl group in one molecule, as well as a cationically electrodepositable paint composition containing as main components said cationic resin and curing agent.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: September 15, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5139631
    Abstract: A cationic electrodeposition coating resin composition composed mainly of(A) a resin containing a primary hydroxyl group and a cationic group, and(B) an epoxy resin which is a copolymer comprising recurring units represented by formula (I) ##STR1## and recurring units represented by formula (II) ##STR2## wherein R denotes a C.sub.3 -C.sub.35 alkyl group, the proportion of the recurring units of formula being 1 to 75% by weight.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: August 18, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Mishida, Akira Tominaga
  • Patent number: 5138018
    Abstract: 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: Grant
    Filed: December 3, 1990
    Date of Patent: August 11, 1992
    Assignee: Fuji Kasei Kogyo Co. Ltd.
    Inventors: Kijuro Tashiro, Ritaro Nagabuchi
  • Patent number: 5132341
    Abstract: A process for the production of cationic paint binders which are particularly suitable for formulating pigment pastes for cathodically depositable electrocoating paints is described. The paint binders produced according to the invention are modified epoxy resin-amine adducts which contain organically-chemically bonded titanium. The cured paint films provide excellent corrosion protection on non-pretreated sheet steel even in the absence of lead-containing compounds and/or lead pigments.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: July 21, 1992
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 5132378
    Abstract: Cathodically depositable paint binders based on epoxy resin/amine adducts modified with diamine bridges which carry longer-chained substituents are described. The diamine bridges are the reaction products of diprimary amines and mono- and diepoxy compounds. The modified epoxy resin/amine adducts have low viscosities and low glass transition temperatures in spite of their high molecular weights. The stoved films, even with higher film thickness, have flawless surfaces and excellent mechanical properties.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: July 21, 1992
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Rudolf Schipfer, Gerhard Schmolzer, Gunther Monschein, Gerhard Meglitsch
  • Patent number: 5130407
    Abstract: A modified epoxy resin composition for use in making a printed circuit board comprising: (1) a modified epoxy resin obtained by reacting (a) a low molecular weight epoxy resin having at least two epoxy groups which has the following formula, ##STR1## (b) an N-heterocyclic fatty amino chain-extending agent at least two active hydrogen atoms and represented by the formulas, ##STR2## and (c) at least one catalyst for catalyzing the reaction between components (a) and (b).
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: July 14, 1992
    Assignee: Industrial Technology Research Institute
    Inventors: Tzong-Ming Lee, Ker-Ming Chen
  • Patent number: 5130004
    Abstract: A pigment paste suitable for use in cationic electrodeposition is disclosed. The pigment paste comprises a cationic resinous grinding vehicle derived from an epoxy resin containing both quaternary ammonium and ternary sulfonium salt groups. Also disclosed are cationic electrodeposition paints containing the pigment paste and the use of these paints in the process of cationic electrodeposition. The paste improves the stability of lead-containing cationic electrodeposition paints.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: July 14, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Mark W. Johnson, Gregory J. McCollum
  • Patent number: 5122578
    Abstract: Compatible compositions comprising polyarylene sulfide-polyphenylene ether copolymers are prepared by the reaction of a polyphenylene ether containing epoxy groups, typically an epoxytriazine-capped polyphenylene ether, with a polyarylene sulfide containing epoxide-reactive functional groups, preferably amine groups. It is sometimes advantageous to anneal said compositions or molded articles prepared therefrom.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: June 16, 1992
    Assignee: General Electric Company
    Inventors: Choong Y. Han, Sterling B. Brown, Erik W. Walles, Tohru Takekoshi, Andrew J. Caruso
  • Patent number: 5112926
    Abstract: This invention provides a epoxy resin composition for structual substrate of PCB comprising a triazine-modified bisphenol A epoxy resin reacted with a multi-functional epoxy resin, a brominated epoxy resin, a curing agent and a curing promoter to form a cured product with excellent thermal resistance (Tg is about 170.degree.-220.degree. C. and mostly higher than 180.degree. C.) as well as good drilling properties and good toughness.Besides, it has comparable electrical and physical properties as the commercially available FR-4 printed circuit boards.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: May 12, 1992
    Assignee: Industrial Technology Research Institute
    Inventors: Tzong-Ming Lee, Ker-Ming Chen
  • Patent number: 5112934
    Abstract: 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: Grant
    Filed: November 27, 1989
    Date of Patent: May 12, 1992
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, H. Craig Silvis
  • Patent number: 5102702
    Abstract: Binder mixtures crosslinkable by radiation comprising as component A a product obtained by reaction of an epoxy compound with more than one epoxide group per molecule with at least one carboxylic acid in a molar ratio of epoxide groups to carboxyl groups of 1:0.5-0.9 and subsequent reaction of the reaction product with at least one unsaturated isocyanatocarbamate esters and as component B a product obtained by reaction of an epoxy compound with more than one epoxide group per molecule with at least one olefinic unsaturated carboxylic acid in a molar ratio of epoxide groups to carboxyl groups of 1:>>1 and subsequent reaction of the reaction product with at least one polybasic carboxylic acid or anhydride(s) thereof, components A and B being present in a weight ratio of 3:1 to 1:3 useful for the product of superior photo-resists and protective lacquers.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: April 7, 1992
    Assignee: Rutgerswerke AG
    Inventors: Ulrich Grundke, Klaus-Peter Liebetanz, Achim Hansen, Jurgen Zehrfeld
  • Patent number: 5096984
    Abstract: A cationically electrodepositable paint composition comprises (A) a resin having hydroxyl groups and cationic groups, (B) an epoxy resin having at least two epoxy groups, each directly bound to a (bridged) alicyclic ring, and (C) lead hydroxide and/or lead maleate as curing catalyst(s).
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: March 17, 1992
    Assignee: Kansai Paint Company, Limited
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5089100
    Abstract: Disclosed herein is a method of incorporating amine functionality onto a polyepoxy resin to be used for cathodic electrocoat. This method has the following steps:a) reacting an epoxy resin with an amount of secondary amine so that unreacted epoxy functional groups remain; andb) further reacting the reaction product of a) with a polyamine so that there is a minimum of one equivalent of epoxy for every mole of polyamine. This method results in an electrocoat bath with the desired high pH and a stable dispersion.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: February 18, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: / Tapan K. Debroy, Ding Y. Chung
  • Patent number: 5077355
    Abstract: A powder coating composition is disclosed which includes an epoxy resin which is solid at room temperature, and a curing agent, characterized in that the curing agent includes an adduct obtained by reaction of (a) a polyfunctional epoxy resin, (b) an imidazole compound having a secondary amino group in the imidazole ring thereof and (c) a polyhydric phenol.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: December 31, 1991
    Assignee: Somar Corporation
    Inventors: Rihei Nagase, Akira Yasuda, Masao Kawashima
  • Patent number: 5076900
    Abstract: A low cure cathodic electrodepositable resin is disclosed. The backbone of the resin is a polyepoxide amine adduct having primary or secondary hydroxyl groups which is crosslinked with aminoplast resins and catalyzed by metal catalysts. The resin is capable of curing in a basic environment at a temperature below 150.degree. C. The resin can be salted with an acid and can be dissolved or dispersed in water. The aqueous dispersions can then be formulated into electrocoat primer coatings for metal objects.
    Type: Grant
    Filed: May 31, 1990
    Date of Patent: December 31, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Willem B. van der Linde, Edward Chu
  • Patent number: 5049249
    Abstract: A low temperature cure electrodepositable cathodic resin is disclosed. The resin is the reaction product of a polyepoxide amine adduct and a novel blocked crosslinking agent. The crosslinking agent of our invention is tetramethylxylene diisocyanate blocked with any suitable blocking agent. The resulting resin can be cured at relatively low temperatures (250.degree.-275.degree. F.), which potentially allows the use of the resin with articles containing plastics.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: September 17, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. DebRoy
  • Patent number: 5026789
    Abstract: A curable impact modified epoxy resin mixture suitable for producing high performance composites is composed ofA. an aromatic epoxy compound,B. an amine type curing agent,C. from 10 to 40% by weight of an aromatic thermoplastic oligomer which contains reactive groups, preferably a polyether sulfone, andD. from 0.1 to 10% by weight of a high molecular weight emulsifier, preferably a phenoxy resin, an epoxy resin or a thermoplastic copolymer, which is compatible not only with the epoxy compound A but also with oligomer C.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: June 25, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Weber, Walter Heckmann, Jurgen Mertes, Helmut Tesch, Volker Altstaedt, Wolfgang Eberle, Thomas Folda, Herbert Stutz, Hans-Gert Recker
  • Patent number: 5008137
    Abstract: Multilayer packaging materials and multilayer containers including a barrier material having excellent resistance to gas permeability are provided. The multilayer packaging materials and containers include at least one permeable polymeric material and at least one layer of a barrier material which is a reaction product of: (i) an ungelled amine-functional polymeric resin, which is a reaction product of a polyamine and a polyfunctional material having at least two functional groups reactive with said polyamine, the ungelled polymeric resin further containing an average of greater than two polyamine moieties per molecule within said resin; and (ii) a material selected from the group consisting of a polyepoxide, a polyoxalate or mixtures thereof, the barrier material characterized as containing at least about four percent by weight amine nitrogen and having an oxygen permeability of less than about 3 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: April 16, 1991
    Assignee: PPG Industries, Inc.
    Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
  • Patent number: 5006615
    Abstract: A modified epoxy resin composition for use in making a printed circuit board comprising: (1) a modified epoxy resin obtained by reacting (a) a low molecular weight epoxy resin having at least two epoxy groups which have the following formula, ##STR1## (b) a mono-nucleus chain extending agent containing N-heterocyclic fatty groups and at least two active hydrogen atoms and represented by the formulas, ##STR2## and (c) at least one catalyst for catalyzing the reaction between components (a) and (b).
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: April 9, 1991
    Assignee: Industrial Technology Research Institute
    Inventors: Tzong-Ming Lee, Ker-Ming Chen
  • Patent number: 5006611
    Abstract: Heat-curable compositions of matter which are stable on storage and which contain(a) 10-70 parts by weight of an epoxy resin having a functionality of at least 3,(b) 90-30 parts by weight of an epoxy resin having a functionality of 2-2.5,(c) a diphenol, the amount of the diphenol being so chosen that 0.6-1.2 hydroxyl equivalents of the diphenol (c) are employed per epoxide equivalent of the epoxy resins (a) and (b), and(d) 10-150 parts by weight, relative to 100 parts by weight of the components (a) to (c), of a thermoplastic having phenolic end groups and having a glass transition temperature of at least 150.degree. C. which is compatible with the mixture of the components (a) to (c), are particularly suitable for the production of prepregs for fiber-reinforced composite materials or for the production of adhesive films. The cured shaped articles obtained therefrom are distinguished by a high heat distortion point and excellent mechanical strength properties.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: April 9, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schmid, Sameer H. Eldin
  • Patent number: 4992516
    Abstract: Cathodically depositable paint binders based on epoxy resin/amine adducts modified with diamine bridges which carry longer-chained substituents are described. The diamine bridges are the reaction products of diprimary amines and mono- and diepoxy compounds. The modified epoxy resin/amine adducts have low viscosities and low glass transition temperatures in spite of their high molecular weights. The stoved films, even with higher film thickness, have flawless surfaces and excellent mechanical properties.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: February 12, 1991
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Rudolf Schipfer, Gerhard Schmolzer, Gunther Monschein, Gerhard Meglitsch
  • Patent number: 4990575
    Abstract: Disclosed are novel compositions derived from polyoxyalkylene amines comprising olefin-terminated polyoxyalkylene ureas prepared by reacting polyoxyalkylene amines of the formula: ##STR1## with isopropenyl dimethylbenzyl isocyanate represented by the formula: ##STR2## said composition being represented by the formulas: ##STR3## where R'=H or methyl or ethyl and R" is the nucleus of a trifunctional polyol such as glycerine, trimethylolpropane, etc. and x has a value of 2 to 70.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: February 5, 1991
    Assignee: Texaco Chemical Co.
    Inventors: Jiang-Jen Lin, George P. Speranza
  • Patent number: 4981884
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with an acid, containing(A) a chain-extended, amine-modified epoxy resin obtainable by reacting(a.sub.1) 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(a.sub.2) a diketimine of a diprimary diamine, which diprimary diamine contains no further groups reactive with epoxy groups under mild conditions and(B) an amino-modified epoxy resin obtainable by reactingb.sub.1) an epoxy resin having an average molecular weight M.sub.n of from 800 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(b.sub.2) a secondary amine or a secondary-tertiary diamine, a ketimine of a primary monoamine or a ketimine of a primary/tertiary diamine or a mixture of these (b.sub.2) components, with the proviso that (A) and (B) are different.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: January 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 4973613
    Abstract: Cathodically depositable electrodeposition paints contain binder combinations of cationic film-forming resins with organic titanium compounds which are obtained by reacting tetraalkyl orthotitanates or titanium acetyl acetonates with NH-functional .beta.-hydroxyalkylamine compounds, subsequently reacting with formaldehyde and with removal of the alcohol and/or acetyl acetone formed. The stoved paint films exhibit an excellent anti-corrosion effect on non-pretreated sheet steel.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: November 27, 1990
    Assignee: Vianova Kunstharz A.G.
    Inventor: Willibald Paar
  • Patent number: 4957995
    Abstract: 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: Grant
    Filed: September 5, 1989
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii
  • Patent number: 4950722
    Abstract: The invention relates to an unsaturated-epoxy moiety R--NHCO.sub.2 --E wherein R is unsaturated and free of isocyanate functionality and E has an oxirane ring. The moiety may be dissolved in a liquid epoxy compound. The invention also relates to a mixture obtained by vinyl polymerization of the moiety and an added unsaturated compound in the liquid epoxy compound solution. Epoxy cross-linking then leads to a polymeric reaction product. Vinyl polymerization and epoxy curing can also be simultaneous. A polymeric material is formed by reacting an isocyanate compound having the formula R--NCO with an epoxy compound having the formula E--OH, where R and E are as defined above, to form the moiety R--NHCO.sub.2 --E and polymerizing this moiety, along with an additional unsaturated compound under vinyl polymerization conditions and in the presence of a liquid epoxy compound, to form a copolymer of R--NHCO.sub.2 --E with the additional unsaturated compound.
    Type: Grant
    Filed: January 5, 1989
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 4931496
    Abstract: 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: Grant
    Filed: March 24, 1989
    Date of Patent: June 5, 1990
    Assignee: Amoco Corporation
    Inventors: Shahid P. Qureshi, Hugh C. Gardner, Richard H. Newman-Evans
  • Patent number: 4931157
    Abstract: An ungelled reaction product of a polyepoxide and an active hydrogen-containing material containing at least two active hydrogens per molecule is disclosed. The active hydrogen-containing material being a hydroxyalkyl-substituted urethane in which the hydroxy group is in the beta position to the urethane group. The reaction product is useful as a precursor in making cationic resins for use in cationic electrodeposition.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: June 5, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Joseph T. Valko, Joseph E. Plasynski, Robert D. Miller
  • Patent number: 4927865
    Abstract: Anthraquinones of formula I ##STR1## wherein X is the group --CR.sup.2 R.sup.3 --, where R.sup.2 is H, --CH or C.sub.1 -C.sub.5 -alkyl and R.sup.3 is H or --CN, R.sup.1 is H or C.sub.1 -C.sub.5 -alkyl and R is a direct bond or linear or branched C.sub.1 -C.sub.18 -alkylene which, alone or together with the --CR.sup.2 R.sup.3 -- group, can be interrupted by one or more --O-- when R.sup.2 and/or R.sup.3 are not --CN, and curable compositions comprising (a) an epoxy resin, (b) a hardener if necessary, (c) an anthraquinone of formula I and (d) an amino alcohol. The cured compositions are photosensitive and are suitable for the preparation of coatings and metallic images by electroless metal deposition.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: May 22, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Duthaler, Jurgen Finter, Walter Fischer, Visvanathan Ramanathan
  • Patent number: 4918157
    Abstract: 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: Grant
    Filed: September 28, 1988
    Date of Patent: April 17, 1990
    Assignee: Amoco Corporation
    Inventors: Hugh C. Gardner, Richard H. Newman-Evans
  • Patent number: 4912179
    Abstract: A new thermocurable composition is disclosed which comprises a Bisphenol A-type epoxy resin having a number average molecular weight of 650-1300, 10-40% by weight of the Bisphenol A-type epoxy resin having an epoxy equivalent of 180-195; and a curing agent capable of cross-linking the epoxy resin. The curing agent is preferably a compound 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 attractive group; R is a lower alkyl; and m and n each is an integer of 1-4, or a mixture thereof with a primary amine, a phenolic compound or an acid anhydride.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: March 27, 1990
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Shinkichi Murakami, Osamu Watanebe, Sadahisa Wada, Makoto Miyazaki, Hiroshi Inoue
  • Patent number: 4900848
    Abstract: 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 fiber-reinforced composite material containing as matrix a cured product of said epoxy resin composition and a fiber as reinforcing material.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: February 13, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii, Hiroshi Nakamura
  • Patent number: 4900415
    Abstract: A low temperature cure electrodepositable cathodic resin is disclosed. The resin is the reaction product of a polyepoxide amine adduct and a novel blocked crosslinking agent. The crosslinking agent of our invention is tetramethylxylene diisocyanate blocked with any suitable blocking agent. The resulting resin can be cured at relatively low temperatures (250.degree.-275.degree. F.), which potentially allows the use of the resin with articles containing plastics.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: February 13, 1990
    Assignee: E. I. Du Pont de Nemours & Company
    Inventors: Ding Yu Chung, Tapan K. DebRoy