Abstract: Water-dilutable resinous products are obtained by reacting(A) a resin having at least one phenolic hydroxyl group and a free position ortho and/or para to a phenolic hydroxyl group, and containing a residue formed by polymerization of a vinyl monomer in the resin or in a precursor thereof,(B) an aldehyde, and(C) sulphurous acid or an organic acid containing a primary or secondary amino group or a mercaptan group and a carboxylic, sulphonic or phosphonic acid group, or a water-soluble salt thereof.Aqueous compositions containing the resinous products and, if required, and aminoplast, a phenoplast or a blocked polyisocyanate, usually together with a minor amount of an organic solvent, are useful in the formation of surface coatings.

Abstract: A curable composition is prepared by reacting (1) an alkenylphenyl cyanate or mixture thereof, (2) an aromatic polycyanate, polycyanamide or mixture thereof and (3) a polymerizable ethylenically unsaturated material or mixture of such materials. Said curable compositions provide polymeric (cured) compositions with improved mechanical strength relative to cured aromatic polycyanates and/or polycyanamides.

Abstract: A transparent moisture-resistant mercaptan composition is made utilizing an amino-titanate catalyst. The composition can be utilized in association with high heat-resistant transparent compositions containing a boroxine compound.

Abstract: A latent curing agent for epoxy resin, characterized in that the latent curing agent is an adduct obtained by reacting (a) a polyfunctional epoxy compound, (b) a compound having at least one OH, NH.sub.2, NH or SH group together with a tertiary amino group in the molecule and (c) a carboxylic acid anhydride is a good curing agent for epoxy resins. The present curing agent is useful in formulating storable, one-package, heat-curable epoxy resin-based compositions.

Abstract: An addition product obtained by reacting (a) a polyfunctional epoxy compound and (b) a compound having at least one functional group of OH group, SH group, COOH group and CONHNH.sub.2 group together with a tertiary amino group in the molecule, and an addition product obtained (a), (b) and (c) an organic compound having two or more active hydrogen atoms in the molecule (excluding a compound having an epoxy group or tertiary amino group) are good curing agents for epxoy resin. The curing agents are useful in formulating novel storable one-package, heat-curable epoxy resin-based compositions.

Abstract: Resin compositions are prepared by reacting an epoxy resin with an amine-substituted aromatic sulfonic acid amide at a temperature up to about 130.degree. C. The resultant product can be cured by heating to a temperature of at least about 150.degree. C. in the presence of suitable curing agents and in some instances in the absence of any curing agent.

Abstract: Curable epoxy resin compositions are described which comprise a mixture of an acid curable epoxy resin and a minor amount of an oxidizing agent capable of reacting with sulfur dioxide to form a catalyst for curing said epoxy resin. The curable epoxy resin composition may contain solid particulate materials. The procedures for curing such epoxy resins as well as methods for forming sand cores and molds also are described. Sand cores and molds produced in accordance with the method of the invention have sufficient strength and hardness after a few seconds of curing for normal foundry applications.

Abstract: The invention provides 2-hydroxypropane sulphonic acid derivatives of general formula ##STR1## wherein n is a number having an average value from 0 to 12, .circle.A denotes saturation or aromatic unsaturation in an associated carbocyclic ring and the or each of the R.sup.1 and R.sup.2 groups are independently selected from hydrogen and C.sub.1-12 alkyl groups provided that each --C(R.sup.1)(R.sup.2)-- group contains not more than 13 carbon atoms; and salts thereof; a process for their preparation and curable compositions containing them.

Abstract: Water-soluble or water-dispersible resinous salts are prepared by `tipping` an epoxy resin with a phenol, then carrying out a Mannich reaction with an aldehyde (usually formaldehyde) and an aminosulfonic or aminophosphonic acid, followed by salt formation on the free acid groups, preferably using an aliphatic amino alcohol, e.g., 2-dimethylaminopropan-1-ol.Such salts may be crosslinked by heating in the presence of an aminoplast, a phenol-formaldehyde resin or a blocked polyisocyanate or, when the salts contain free methylol groups, by heating alone. They can be used for preparing coating compositions.

Abstract: A resinous hardener system comprising the reaction product of diamino diphenylsulfone compounds and diglycidyl ethers of polyhydric phenols. The hardener system can be incorporated into a variety of epoxy resins for use as improved prepreg or laminating resins, as resin molded castings, and the like.

Abstract: Dimercaptodihydroxy alkanes are used as a curing agent for epoxide resins and as ore flotation agents.

Abstract: Aqueous thermosetting coating compositions are disclosed characterized by reduced curing requirements and which produce coatings having superior cured properties. These coatings comprise water containing water miscible organic solvent and the compositions have dispersed therein, based on total resin solids, from 25% to 85% of carboxy-functional organic solvent-soluble copolymer salt with a volatile amine in which the copolymer contains hydroxy groups providing an hydroxyl value in the range of 30 to 300, from 5% to 40% of a water soluble or water dispersible aminoplast or phenoplast curing agent, and from 2% to 35%, of a water dispersible epoxy phosphate ester polymer which is an oxirane-function-free, salt reaction product of (1) a monoester reaction product containing residual epoxy functionality, of (a) a resinous polyepoxide having at least about 1.4 oxirane groups per molecule, and (b) less than 0.

Abstract: Certain water-soluble substituted phenol formaldehyde type copolymers retain their viscosities in high brine environments and are highly useful as surfactant-mobility control agents in oil recovery processes.

Abstract: An epoxy resin substantially represented by the general formula ##STR1## where Ar.sup.1 is a residual group of a dihydric phenol derived from a compound having one or two benzene nuclei, Ar.sup.2 is residual group of a halogen-substituted benzenoid compound having two halogen atoms on its nuclei and represented by the formula --Ar.sup.3 --Y--Ar.sup.4 -- where each of Ar.sup.3 and Ar.sup.4 is a hydrocarbon group having a divalent benzene nucleus and Y is a sulfone group or a carbonyl group, and n is an integer of from 1 to 50.

Abstract: This invention is an aqueous-dispersible oxirane formulation comprising an oxirane and a cross-linking amount of 3-hydroxythiophane and an organic acid having at least 2 acid moieties that have a dissociation constant, pK.sub.a, less than 4.75.

Abstract: An improved process for reacting vicinal epoxides with phenols or thiophenols is described. This process is conducted at essentially anhydrous conditions and temperatures less than 175.degree. C. The resulting resins are generally more linear and less colored than advanced resins produced via prior art processes. Also the phosphonium catalyst remains active to promote subsequent advancement or curing reactions. The catalyst can be deactivated in a separate step to produce a resin of exceptional purity.

Abstract: This invention relates to novel N-cyano amide compositions and adducts thereof of the formula ##STR1## wherein R is a simple organic moiety or a polymeric adduct with the valence of n and n is 2 or 3. The composition, per se, can be used as a curing agent for epoxy resins to form a thermoset material on heating.

Abstract: Water dispersible epoxy-phosphate ester polymer salts are disclosed which exhibit improved stability in coating compositions contining aminoplast or phenoplast resin. These salts are provided by reacting a resinous polyepoxide having at least about 1.4 oxirane groups per molecule with less than 0.9 mol of orthophosphoric acid for each oxirane equivalent in the polyepoxide to form a monoester reaction product containing residual epoxy functionality. The monoester reaction product so-provided is then reacted with at least 1 mol of a volatile amine per equivalent of oxirane functionality in said monoester to provide a water dispersible product lacking oxirane functionality. Ether alcohols, and especially 2-butoxy ethanol, are relied upon to provide dispersions having low viscosity.

Abstract: Resinous salts, prepared by thioalkylation or sulfoalkylation of a phenol obtained by advancement of a polyepoxide, followed by at least partial neutralization, have the general formula ##STR1## where R.sup.- represents a group of formula --S--R.sup.1 --COO.sup.- or a group of formula --SO.sub.3.sup.- ; R.sup.1 represents an aliphatic, aromatic or araliphatic divalent group which may contain a further group --COO.sup.- M.sup.+ ; R.sup.2 represents --H or alkyl; one of R.sup.3 and R.sub.1.sup.3 represents a hydroxyl group and the other represents --H, halogen, alkyl, or alkenyl; each R.sup.4 represents --H, halogen, alkyl, or alkenyl; R.sup.5 represents --H, halogen, alkyl, alkenyl, or a group --CH(R.sup.2)OH, --CH(R.sup.2)OR.sup.8, or --CHR.sup.2 --R.sup.- M.sup.+ ; R.sup.6 represents the residue of a polyepoxide, preferably of average mol. wt. 1000-5000; each of the groups R.sup.7, which may be the same or different, represents --H or a covalent bond linked to the group R.sup.6 ; R.sup.

Abstract: The gel time of curable epoxy resin compositions are controllably reduced by adding to the epoxy resin-curing agent mixture between about 0.1 and about 10% elemental sulfur.

Abstract: Extremely rapid ambient curing of polyepoxide resins and mixtures of polyepoxide resins and polyacrylate esters is achieved by use of a curing system composed of at least one polymercaptan and at least one catalytic co-curing agent which is the condensation product of:(a) aliphatic amine or substituted aliphatic amine containing at least one primary aliphatic amine group where the aliphatic moiety is ethylene or greater with(b) at least one amino acid, its corresponding lactam or other amide forming derivative.Optionally, known Lewis Base catalysts for the epoxy/mercaptan reaction, such as tertiary amines, may also be used.

Abstract: A self curing aqueous solution/dispersion comprising about 50-70 wt. % water, about 25-35 wt. % of a novel N-polymethylene substituted polyoxypropylene polyamine and about 3-9 wt. % of a curable polymer-forming component such as an epoxy-resin is described. The solution is useful for injection into permeable earth formations such as unconsolidated sands to reduce their permeability and consolidate the formation. Novel N-substituted polyamines of the formula [NaO.sub.3 S--R.sub.1 ].sub.m A wherein R.sub.1 is a C.sub.2 to C.sub.6 polymethylene group and A is a polyoxyalkylene polyamine are employed in the solution to render the epoxy-resin component adequately soluble or dispersible in the aqueous solution and to act as the curing agent for the resin.

Abstract: Amphoteric amino sulfonate derivatives of epoxy resins having at least one terminal group of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.20 alkyl or substituted alkyl, and R.sub.4 is C.sub.1 -C.sub.6 alkylene or substituted alkylene, which are reaction products of an epoxy resin having a plurality of terminal groups of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined, with an amino sulfonate of the formula:R.sub.3 --NH--R.sub.4 --SO.sub.3 Mwherein R.sub.3 and R.sub.4 are as defined, and M is a cation.

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: Thermosetting high solids coating compositions which: (i) cure, at least in part, by reaction between an amine-aldehyde compound and hydroxyl functionality on a film-forming component, which hydroxyl functionality is either generated in situ during the cure of the composition or is both generated in situ during cure and is present on the film-forming component prior to curing; (ii) are adapted for low temperature bake applications; and (iii) contain greater than about 55% by weight of nonvolatile solids.

Abstract: Disclosed is a method of imparting water solubility or dispersibility to the reaction product of a polyepoxide and a mercapto-substituted triazole, a mercapto substituted tetrazole or a mixture thereof, by admixture with a base in an amount at least sufficient to water solubilize the azole-functional reaction product.Also disclosed is a method of using the above water solubilized reaction product in an electrodeposition process.

Abstract: The invention is directed to curable compositions comprising an azole-functional resin and a labile metal-ligand complex. The azole-functional resin is the reaction product of a monomeric or polymeric resin and a reactive N-heterocyclic compound containing at least two nuclear nitrogen atoms in a 5-membered ring structure capable of forming stable metal-ligand complexes. Mixtures of azole-functional resins also may be used with the labile-metal ligand complexes in the compositions of the invention.

Abstract: Thermosetting high solids coating compositions which: (i) cure, at least in part, by reaction between an amine-aldehyde compound and hydroxyl functionality on a film-forming component, which hydroxyl functionality is either generated in situ during the cure of the composition or is both generated in situ during cure and is present on the film-forming component prior to curing; (ii) are adapted for low temperature bake applications; and (iii) contain greater than about 55% by weight of nonvolatile solids. The claimed high solids coating compositions, exclusive of pigments, solvents and other nonreactive components, consist essentially of:(A) a film-forming component selected from the group consisting of an epoxy functional copolymer and polyepoxide resin;(B) a latent reactive catalyst comprising the reaction product of (i) a copolymer bearing pendent epoxy functionality, and (ii) a particular sulfonic acid;(C) an amine-aldehyde crosslinking agent; and(D) an optional hydroxy functional additive.

Abstract: Water soluble binders for can lacquers are prepared by reacting an epoxy resin (polyglycidyl ether of polyhydric phenol) with an aliphatic amino carboxylic acid, e.g., (glycine, alanine, glutamic acid), wherein at least 50% of the acid groups have been neutralized with a base (alkali metal hydroxide, tertiary amine or quaternary ammonium hydroxide.

Abstract: A catalyst for forming ambient temperature stable diamino-diphenyl sulfone-epoxy composition comprises the half-salt of a strong aromatic sulfonic acid such as toluene sulfonic acid and an imidazole, preferably an alkylated imidazole such as 2-ethyl-4-methylimidazole. The composition fully cures at moderate temperature to form a humidity resistant resin having a high heat distortion temperature and can be impregnated onto reinforcing fibers such as graphite to form composites.

Abstract: A resinous hardener system comprising the reaction product of diamino diphenylsulfone compounds and diglycidyl ethers of polyhydric phenols. The hardener system can be incorporated into a variety of epoxy resins for use as improved prepreg or laminating resins, as resin molded castings, and the like.

Abstract: Thermosetting compositions comprising: (A) a sulfonic acid ester comprising the reaction product of an epoxy functional polymer bearing hydroxyl functionality, and a sulfonic acid having the formula ##STR1## wherein R is selected from linear or branched alkyl groups and aryl groups; and (B) an amine aldehyde crosslinking agent.During cure of the composition, component (A) breaks down to form not only a reactive sulfonic acid catalyst, but also the hydroxy functional film forming material which crosslinks with the amine aldehyde crosslinking agent.

Abstract: Water-thinnable, heat curable binders for coatings are prepared by reacting a polyglycidyl ether of a polyhydric phenol with neutralized sulphanilic acid in a ratio of from 0.9 to 1.1 aminohydrogen equivalents per epoxy equivalent.

Abstract: Compositions of matter comprising a liquid thiol terminated polysulfide polymer, a liquid epoxy resin and a liquid amine terminated polymer containing from about 1.7 to about 4 amine groups per molecule of the general formula ##STR1## wherein Y is a univalent radical derived by removal of an amine hydrogen from an aliphatic, alicyclic, heterocyclic or aromatic amine containing from 2 to about 20 carbon atoms and at least 2 amino groups and B is a polymeric backbone comprising carbon-carbon linkages are disclosed. Insulated window units fabricated therefrom possess superior mechanical and dewpoint retention properties.

Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst comprising the reaction product of (i) a copolymer bearing pendent epoxy functionality, and (ii) a sulfonic acid having the formula ##STR1## wherein R is selected from linear or branched alkyl groups and aryl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.

Abstract: Antioxidant compositions as described which are the reaction products of a mixture of(a) at least one compound selected from compounds having the formula ##STR1## wherein each Ar is an aromatic group, and R and R.sup.1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R.sup.2 --COOH groups wherein R.sup.2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R.sup.1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, andAr--NH--Ar--O--R.sup.3 (FORMULA II)wherein Ar is as defined above and R.sup.3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R.sup.2 --COOH wherein R.sup.2 is an alkylene or alkenylene group, and(b) at least one polyepoxide having at least 2 epoxy groups per molecule.

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: A prepolymer is comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide in combination with an aromatic and/or a cycloaliphatic epoxy resin providing at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.

Abstract: Thermosetting compositions comprising a film forming component bearing or capable of generating hydroxyl functionality, amine-aldehyde crosslinking agent, and a latent reactive catalyst having the formula: ##STR1## wherein R is selected from alkyl or aryl groups and X is selected from 2-hydroxycycloalkyl and aryl substituted 2-hydroxycycloalkyl groups.Preferred compositions within the scope of the invention include high solids, thermosetting coating compositions suitable for automotive applications.

Abstract: A prepolymer comprised of the reaction product of at least one aliphatic bismaleimide, at least one aromatic amine and at least one aromatic bismaleimide is combined with at least one cycloaliphatic epoxy resin having a melting point less than about 120.degree. F. and at least two functional epoxy groups to provide a low temperature curable composition. The cured products are strongly adherent to a variety of substrates.

Abstract: Novel chain-extended cationic resinous products suitable for use in cationic electrodeposition are disclosed. The products are formed by chain extending polyepoxides with polymercapto compounds and reacting with amines to provide cationic groups.

Abstract: Resinous compositions which are the Michael adducts of primary and/or secondary amines and polymers containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties are disclosed. The compositions are depositable on substrates to form films. The films are amenable to oxidative and aminoplast cures and cure with light color. The compositions are desirable for use in cationic electrodeposition.

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: A cured epoxy resin composition containing high concentrations of liquid polysulfide polymers has improved resistance to thermal cycling and degradation by moisture.

Abstract: A semipermeable membrane composed of a water-insoluble, membrane-forming polymer (hereinafter referred to as "polymer (II)") which is obtained by partially converting the hydroxyl groups of a polymer represented by the following formula (hereinafter referred to as "polymer (I)"): ##STR1## wherein R and R' are halogen, nitro, methyl or ethyl, X stands for a divalent group selected from methylene, ethylene, isopropylidene, ether (--O--), carbonyl (--CO--), sulfide (--S--), sulfoxide (--SO--) and sulfone (--SO.sub.2 --), l and m are integers of from 0 to 4, p is 0 or 1, and n is an integer of from 100 to 1000,to sulfuric acid groups or alkali metal, ammonium or nitrogen-containing basic organic compound salts thereof.

Abstract: Thermosetting liquid coating compositions, based on polymer capable of being crosslinked with nitrogen resin crosslinkers, nitrogen resin crosslinker, and blocked acid catalyst prepared from materials containing at least one oxirane functionality and a sulfonic acid and having a resistivity of at least one megohm are provided. The novel thermosetting coating compositions are particularly useful in electrostatic spraying applications.

Abstract: An improvement in a weldable coating for metallic substrates containing a high molecular weight epoxy or phenoxy resin, an electroconductive pigment such as zinc and a diluent such as a glycol ether wherein the improvement resides in replacing at least about 70 weight percent of said resin with a composition containing a low molecular weight epoxy resin such as the diglycidyl ether of bisphenol A, a phenolic hydroxyl-containing compound such as a phenolic hydroxyl terminated adduct of a diglycidyl ether of a diphenolic compound such as bisphenol A and a catalyst for effecting the reaction between the epoxy resin and the adduct.

Abstract: More rapid curing of polyepoxide resins is achieved by use of a curing system composed of at least one polymercaptan, at least one catalyst which is a poly[(N,N-dimethylamino)alkyl]ether and/or organic non-quaternized salts thereof derived from organic compounds having at least one acidic group and having a pKa greater than about 3.5 and, optionally, organic sulfide, tertiary phosphine or a tertiary amine having no bridged atoms, having no ether oxygen and having at least one tertiary amine group.

Abstract: Reaction of the diphenyl ether with formaldehyde, an alcohol, water and acid catalyst produces a mixture of condensation products that can be cured to useful, thermally stable resins. These condensation products are also useful as functional fluids in capacitors and other electrical devices.

Abstract: Polymeric products comprising the acidified reaction product of an organic polyepoxide and a polyamine containing at least two tertiary amine groups are disclosed. The polyamine and the organic polyepoxide are reacted with one another under conditions to form an internally ionized, quaternary ammonium salt group-containing polymer which has a high molecular weight, but relatively low equivalent weight. The polyamine is formed by reacting an organic polyisocyanate .[.or organic polycarboxylic acid.]. with an active hydrogen-containing tertiary amine. The reaction product is acidified to form the quaternary ammonium salt groups. Preparing the polyamine in this manner gives one wide latitude in determining the final structure of the polyamine. In effect, one can "tailor make" the polyamine by appropriate selection of reactants and exert a great measure of control over the properties of the final polymeric product.