Abstract: Resinous materials are produced in the substantial absence of a solvent by feeding to an extruder operated at a temperature sufficient to cause a reaction between the reactants (A) at least one material having an average of more than one vicinal epoxy group per molecule, (B) at least one material having an average of more than one group reactive with component (A) such as hydroxyl, thiol, carboxyl, isocyanate, thioisocyanate or secondary amine groups or a combination of such groups per molecule or a material having only one primary amine group per molecule, (C) at least one catalyst for promoting a reaction between components (A) and (B) if a catalyst is required to effect the reaction between components (A) and (B), and (D) optionally one or more chain terminators and thereafter recovering a resinous material resulting from the reaction between components (A) and (B) from said extruder.This process is useful in preparing advanced epoxy resins and phenoxy thermoplastic resins.

Abstract: The present invention relates to a water-dispersible self-hardenable resin composition, and particularly to a self-hardenable resin composition, which has a low-temperature hardenability and is adapted for the cationic electrodeposition painting wherein a material to be painted is used as a cathode.The present invention provides a self-hardenable resin composition consisting essentially of a Michael type addition reaction product consisting of 65-95% by weight (in solid base) of a polyamine resin having amino groups and/or imino groups and 35-5% by weight of an ethylenically unsaturated compound having an amine-imido group.

Abstract: There is disclosed herein an amide-containing hydroxyethyl carbamate and a coating composition comprising same. The preparation thereof entails the reaction of an amidoamine and a cyclic organic carbonate.

Abstract: Heat-curable compositions exhibiting improved room temperature pot life and reduced viscosity are obtained from composition comprising (1) a polyepoxide, (2) an aromatic or aliphatic amine, (3) a trihydrocarbyl sulfonium salt, (4) an unsaturated monomer and (5) a free radical curing agent.

Abstract: Heat-curable compositions exhibiting improved room temperature pot life and reduced viscosity are obtained from composition comprising (1) a polyepoxide, (2) an aromatic or aliphatic amine, (3) a trihydrocarbyl sulfonium salt, (4) at least one unsaturated aromatic monomer, (5) an unsaturated co-monomer and (6) a free radical curing agent.

Abstract: A synthetic resin which carries basic nitrogen groups and can be diluted with water as a result of protonation with an acid can be obtained by reacting an epoxy resin, having a mean molecular weight M.sub.n of from 300 to 6,000 and containing on average from 1.5 to 3.0 epoxide groups per molecule, with a diketimine of a primary diamine and, if appropriate, a secondary amine, which may additionally contain a tertiary amino group, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.These resins are useful as binders for coating agents, in particular for the cathodic electrocoating of electrically conductive substrates.

Abstract: Oligomeric vinyl esters are prepared by reacting (A) an epoxy resin prepared by co-oligomerizing (1) a mixed cyanate of a polyphenol and (2) an aromatic polyamine with (B) a monounsaturated monocarboxylic acid.These vinyl ester resins are (oligomeric vinyl ester and copolymerizable monomer blend) useful in the preparation of laminates, composites, castings, coatings and the like.

Abstract: Novel hydroxyaromatic oligomers are prepared by the co-oligomerization reaction of a mixed cyanate of a polyphenol with an aromatic polyamine. These oligomers are useful in preparing epoxy resins therefrom.

Abstract: Solventless polymeric compositions suitable for coatings and moldings are formed by the addition reaction product of a first component comprising mono, di or polyamines, or an adduct of mono, di or polyamines with mono, di or polyfunctional acrylates and/or epoxides and a second component comprising mono, di or polyacrylates or mixtures with mono, di or polyepoxides.

Abstract: A quaternary ammonium group-containing material which is obtained from reacting a polyepoxide with an amine containing at least one acyclic group of about 8 to 30 carbon atoms and optionally an amine containing an alkylarylpoly ether moiety is disclosed. The resins are useful as pigment grinding vehicles and in the formulation of pigment paste, particularly pigment paste with high pigment loadings. When formulated into cationic electrodepositable compositions, the pigment grinding vehicles provide for cured electrodeposited coatings of excellent corrosion resistance, particularly over untreated and oily steel.

Abstract: Cationic heat-hardenable binders comprising polymers containing amine groups and a crosslinking component which is film-forming with the amine group containing polymer through transesterification at elevated temperatures are described. The binders which are water-dilutable upon protonization of the amine groups comprise(a) 60 to 95% by weight of a polymer having a hydroxyl value of from 40 to 450 mg KOH/g and an amine value of from 20 to 150 mg KOH/g, water-soluble or water-dilutable upon protonation of the basic groups, and(b) 5 to 40% by weight of a cross-linking component of the general formula ##STR1## n having a value of from 1 through 5, R.sub.1 being the moiety of a monoalcohol having from 1 to 8 C-atoms or of a polyol or of a polyamine or of a polyepoxy compound or of a polyisocyanate remaining after reaction with one or more carboxylic acid groups, andR.sub.2 being a straight chain or branched alkyl radical with from 1 to 8 C-atoms.

Abstract: The method of hardening a glycidyl compound with a polyether urethane urea amino hardener is disclosed, said hardener being prepared by reacting (1) a blocked prepolymer prepared by reacting a phenolic compound with the reaction product of a polyether polyol with an excess of polyisocyanate, with (2) a polyfunctional amino compound.

Abstract: The invention sets forth novel telechelic (terminally functional) prepolymers which may be reacted to form curable epoxides. On account of the incorporation of saturated elastomer chains into the prepolymers improved epoxides arise having increased moisture resistance and less brittleness than conventional epoxides. These prepolymers may be straight chain or three-armed star, emanating from a common phenyl ring nucleus. Molecular weights of the prepolymers range from about 700 to 50,000 (linear) and from about 1000 to about 75,000 (three-arm star). The epoxides are useful as coatings, in adhesives, as additives, and the like.

Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a malenimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.

Abstract: Curable compositions comprising an epoxide resin and an aliphatic amine curing agent are rendered less viscous, and their rate of cure is accelerated, by the addition of an ester of the formula ##STR1## wherein n represents an integer of from 1 to 6,R represents the residue of a mono- or polyhydric alcohol or phenol after removal of n hydroxy groups, andR.sup.1, R.sup.2, and R.sup.3 may be the same or different and each represents a hydrogen or halogen atom or an alkyl group, or one or two of R.sup.1, R.sup.2, and R.sup.3 may alternatively represent an acyloxy group.Typical such esters of formula I include diphenyl carbonate, bis(phenoxycarbonyloxy) polybutadiene, and tris(phenoxycarbonyloxy) poly(oxypropylene). The compositions may be cured at room temperature and are particularly suitable for use as coatings and castings.

Abstract: The invention relates to polyglycidyl ethers and provides such compounds based on diphenylol C.sub.7 to C.sub.13 alkanes, and their preparation from the appropriate diphenylol alkanes. The polyglycidyl ethers may be cured with known epoxy resin curing agents and may be used as base materials for the preparation of anionic or cationic aqueous thermosetting paint binders.The polyglycidyl ethers exhibit good compatibility with aliphatic hydrocarbon solvents.

Abstract: A curable thermosetting resin, especially suitable for RIM applications, comprising a blend of(a) 100 parts by weight of a polyepoxide, particularly a normally liquid polyepoxide and more particularly a glycidyl polyether of a polyhydric phenol,(b) from about 10 to about 200 parts by weight of at least one ethylenically unsaturated monomer, especially an aromatic monomer, and preferably styrene,(c) a curing amount of an aliphatic or cycloaliphatic polyfunctional amine or a polyamide, and(d) an effective amount of an amine-compatible free-radical initiator.

Abstract: A self-curing modified epoxy resin composition produced by irradiating with electron beams a mixture of an epoxy resin, a quaternary salt of .alpha.,.beta.-unsaturated carboxylic acid ester having one quaternized amine nitrogen in the ester group, and optionally a monomer having one ethylenically unsaturated bond in the molecule, as well as an aqueous dispersion of such resin composition is herein disclosed.

Abstract: Tertiary nitrogen-containing chain-extended epoxy resins, capable of forming stable aqueous emulsions, may be produced by chain-extending an epoxy resin using a tertiary nitrogen containing ether or ester polyol for example, particularly, polycaprolactone which has been polymerization initiated by a tertiary amine polyol such as N-methyl diethanolamine. The corresponding amine salt is formed by treatment with an acid for example acetic acid and the resulting cationic polymer may be dispersed in water to form a cationic emulsion capable of being coated onto a substrate by electrodeposition. The chain extended resins, by virtue by their content of free epoxy groups are also usable for cross-linking and other uses.

Abstract: An amine resin soluble in water with the aid of an acid is produced by reacting a dihydric phenolic compound, such as a bisphenol, with a stoichiometric deficiency of preferably aromatic diepoxide, and then reacting the product containing less than -0.3 part of unreacted dihydric phenolic compound per part of reaction product with at least about 3.25 mol of formaldehyde per mol of said reaction product and with monosecondary amine to produce a Mannich base. This Mannich base is then reacted with additional diepoxide in an amount of from 0.5 to 2 epoxy equivalents per epoxy equivalent in the initially used diepoxide.

Abstract: The process according to the invention is performed by reaction of epoxide resins with primary and/or secondary polyamines with simultaneous quaternizing by means of aromatic and aliphatic polysulfonic esters, halogen-free organic phosphoric esters, or organic compounds which contain at least 1 chlorine or bromine atom, and which are free from -COOH groups and corresponding salt groups. The crosslinked plastics thus obtained are distinguished by an improved electrical conductivity.

Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a maleimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.

Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.

Abstract: Diglycidyl ethers are prepared from a mixture of isomers of 1,1-bis(hydroxyphenyl)heptane. The diglycidyl ethers have low viscosity and good compatibility with aliphatic hydrocarbon solvents; they can be cured with the usual curing agents for epoxy resins, e.g., polyamines, and can be used in solventless coating compositions.

Abstract: A polyspirolactone polymer particularly suitable for protective surface coatings comprises a spirolactone structure in the polymer structure adapted to be cross-linked with a primary or secondary amine compound to produce a thermoset protective coating.

Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.

Abstract: Novel compositions of matter comprising the reaction product of beta-diketones and epoxy resins blended with monomeric or polymeric phosphonium salts are hereby provided. The beta-diketones useful herein are those which enolize in amounts that render them sufficiently acidic and reactable with epoxy groups of the resin. The novel reaction products can be dispersed in water to form pretreatment agents and they can be formulated with curing agents to form coating compositions. Ferrous metals treated with the compositions of this invention exhibit excellent corrosion resistance properties.

Abstract: Novel compositions of matter comprising a water-dispersible reaction product of beta-diketones and epoxy material are hereby provided. The beta-diketones useful herein are those which enolize in amounts that render them sufficiently acidic and reactable with epoxy groups of the resin. The novel reaction products can be dispersed in water and they can be formulated optionally with curing agents. Ferrous metals treated with the compositions of this invention exhibit excellent corrosion-resistant properties.

Abstract: High molecular linear, thermoplastic, epoxide-amine-adducts containing the structural segment ##STR1## are prepared by a solvent-free reaction of equivalent amounts at 20 to 200.degree. C. of N,N'-bis(aralkyl) diamines (for example, N,N'-dibenzyl-ethylenediamine, N,N'-dibenzyl-p-xylylenediamine, N,N'-dibenzyl-4,4'-diamino-diphenylmethane, N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8) with diepoxides (for example, 2,2-bis(4-glycidyloxyphenyl)propane). The polyadducts are soluble and may be processed by thermoplastic methods. The polyaddition process may be conducted for the forming of shaped objects in a form-shaping vessel, for the production of coatings directly upon the surface to be coated and also in the presence of inserted materials and has, due to these characteristics, the nature of a casting system.

Abstract: Polymer polyol dispersions are prepared by reacting polyepoxides with epoxide resin hardeners in the presence of polyester and polyoxyalkylene polyether polyols.

Abstract: A process for preparing a flame-retardant antistatic polymer additive useful for incorporation into the melt prior to extruding fibers or other polymers or for dispersing on fibers. Improved flame-retardant properties are obtained by including with said flame-retardant additive an effective flame-retardant proportion of a compound from group Vb of the periodic table.

Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a maleimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.

Abstract: An epoxy resin composition which comprises (1) an epoxy resin having at least two epoxy groups per molecule and (2) an amine having at least one perfluoroalkyl group and at least one primary and/or secondary amino groups per molecule can be readily cured to afford a cured product, which shows excellent water resistance, oil resistance and stainproof property.

Abstract: The present invention deals with unique substituted ammonium compounds for use in cationic electrodeposition processes.

Abstract: Primary diamines of the formula ##STR1## wherein R is a straight chain saturated hydrocarbon of 2 to 4 carbons, a disubstituted benzene ring, or disubstituted dibenzo methane for use as a curing agent for epoxy resins. These curing agents can be used to form epoxy resin mixtures useful in filament winding and pre-impregnated fiber molding and in formulating film adhesives, powder coatings and molding powders. The epoxy mixtures form for such uses as room temperature non-reacting, intermediate stable state which has a latent cross-linking capability.

Abstract: Flame-retardant antistatic polymer additives are provided which inhibit the buildup of electrostatic charges upon the addition of such compositions to synthetic polymeric fibers, i.e., polyamide fibers, and at the same time do not contribute to the flammability characteristics of such polymeric fibers. The flame-retardant antistatic polymer compositions are useful in combinations with fibers such as polyamide, polyester, polyurea, polyurethane, polysulfonamide, polyolefin and polyacrylic fibers. The antistatic effect is obtained by the process of coating the fibers or dispersing in or on the fibers up to about 12 percent by weight of a polymer composition which is the reaction product of:(a) a polyoxyalkylene compound or polyester thereof and(b) at least one reactant selected from the group consisting of (1) a diol, (2) a polyester and (3) an aliphatic or aromatic diacid or derivative of (3), wherein at least one said reactant is halogenated.

Abstract: Novel carboxylic acid metal salt/amine complexes of the formula(A.sup..crclbar.).sub.2 Me.sup.2+ .multidot.NH.sub.2 --R.sub.1 --NH.sub.2in which A is the anion of cyanoacetic acid, pyrrolidonecarboxylic acid, maleimidylcarboxylic acid, succinylimidylcarboxylic acid, benzenesulphonic acid or toluenesulphonic acid or of a methanephosphonic acid monoester or benzenephosphonic acid monoester, Me.sup.2+ is a divalent metal cation and R.sub.1 is a long-chain polyoxyalkylene radical, are obtained by reacting 1 mol of a carboxylic acid metal salt of the formula(A.sup..crclbar.).sub.2 Me.sup.2+with 1 mol of a diamine of the formulaH.sub.2 N--R.sub.1 --NH.sub.2in a polar organic solvent and in the temperature range of 25.degree. to 200.degree. C. to give the complex compounds of the formula.The novel complex compounds are valuable curing agents for epoxide resins and in mixtures with epoxide resins have an advantageous storage stability.

Abstract: Curable mixtures of polyepoxide compounds which contain an amine curing agent have longer curing times, and thus, in particular, good workability when used as adhesives, when N,N-dimethylethylenediamine derivatives or N,N-dimethyl-1,3-propylenediamine derivatives are used as the curing agents. The mechanical properties are also frequently improved.

Abstract: Curable resinous compositions containing primary and/or secondary amine groups which are non-volatile under curing conditions and containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties which are reacted with a primary and/or secondary amine which are volatile under curing conditions are disclosed. The compositions are depositable on a substrate to form films.

Abstract: Heavy reaction product after separation as by distillation of light reaction product or diadduct from a reaction mixture obtained by reaction of olefinically unsaturated nitriles with monoolefinic hydrocarbons containing an allylic hydrogen atom is hydrogenated to produce a polyamine mixture. The mixture thus produced is useful as an epoxy resin hardener yielding cured resins exhibiting low water absorption.

Abstract: The reaction product of an epoxide and a polyalkylenepolyamine is prepared in bead form by dispersing a blend of the epoxide and polyalkylenepolyamine in a concentrated aqueous solution of an alkali metal hydroxide and then curing the dispersed blend. For example, dispersing a blend of triethylenetetramine and diglycidyl ether of bisphenol A in an agitated aqueous solution of 50 weight percent NaOH and curing the dispersed blend produces normally solid beads which are useful as a weak base ion exchange resin.

Abstract: The cured reaction product of a polyalkylenepolyamine and a polyepoxide is useful as a weak base ion exchange resin. For example, the reaction of triethylenetetramine and diglycidyl ether of bisphenol A forms a weak base resin having an excellent total weak base capacity.

Abstract: Curable compositions are prepared comprising an epoxide compound or a mixture of epoxide compounds having an average of at least two epoxide groups per molecule, and as a curing agent, a cyanamide of an organic primary amine or a mixture of cyanamides of organic primary amines having an average of more than one cyanamide moiety per molecule. Such compositions are useful in molding, casting, laminating and coating applications.

Abstract: Weldable coatings containing, an electro-conductive pigment such as zinc, an epoxy resin binder and solvent are improved by employing as the epoxy resin binder, the reaction product of a relatively low molecular weight epoxy resin such as the diglycidyl ether of bisphenol A and an amine compound having two amine hydrogen atoms such as ethanolamine.

Abstract: Novel resinous binders useful for coating articles by cathodic electrodeposition are described. These binders contain tertiary amino groups and are derived from glycidyl esters of alpha-branched monocarboxylic acids containing from 6 to 20 carbon atoms in the acid group.

Abstract: A method of cationic electrodeposition on an electroconductive substrate is disclosed. The method of the invention employs as the electrocoating vehicle an aqueous dispersion of a quaternary ammonium carbonate-containing resin. Electrodeposition of the resin is accomplished without generating harmful acid from the counter ion. The carbonate counter ion is continuously evolved from the electrodeposition bath at the anode as carbon dioxide.The quaternary ammonium carbonate-containing polymers are also useful as feed resins for controlling the pH of aqueous dispersions of acidified cationic resins used in electrodeposition. Upon electrodeposition, these resins generate acid which can build up to undesirable levels in the electrodeposition bath. The quaternary ammonium carbonate-containing polymers are relatively basic and when fed into the bath react with the acid to form the corresponding quaternary ammonium salt of the acid releasing carbon dioxide.

Abstract: Epoxy resins, particularly those of the polyglycidyl ether of a polyhydric phenol type, are cured by incorporating therein a polyoxyalkylenepolyamine usually with an accelerator such as a combination of piperazine and an alkanolamine. Rapidity of curing is further improved by substituting from about 50 wt% to 100 wt% of the dithiocarbamate salt of the polyoxyalkylenepolymine for the polyoxyalkylenepolyamine. The epoxy resin products are useful in protective coatings, adhesives, seamless and terrazzo flooring, castings, laminates, and in grouting, potting, encapsulating, caulking and sealing compositions.

Abstract: Low-temperature curing epoxy compositions are described comprising (1) a saturated epoxy resin, (2) a curing amount of certain aliphatic amines and (3) an organic solvent selected from the group consisting of alcohols, glycols, and glycol ethers.

Abstract: Epoxide materials suitable for use in flexible adhesives are prepared by reacting a diene, such as butadiene or isoprene, with an electron donor, typically an alkali metal, in the presence of a polyepoxide normally in a molar ratio diene:polyepoxide of less than 3:1. The polyepoxide is typically a conventional epoxy resin such as DGBA. The product normally separates into two phases, the upper of which comprises epoxy-terminated diene oligomers with degrees of polymerization of about 6 to 14. This separation may be avoided by incorporating a minor proportion of acrylonitrile into the product by addition to either the original diene or the anionic living polymer immediately before hydrolysis. The products may be cured with conventional epoxide curing agents to give an internally flexibilized adhesive having useful combinations of tensile and shear strengths.

Abstract: To accelerate the curing of epoxide resins by aromatic, heterocyclic, or cycloaliphatic polyamines there are employed salts of trifluoromethanesulfonic acid.