Abstract: A two-part composition curable by contact of respective parts with one another, comprising: a first part comprising a cationically polymerizable material and a first latent curing component; and a second part comprising a cationically polymerizable material and a second latent curing component which is reactive with the first component to form cations which are curingly effective for the resin. A preferred class of cation species comprises carbenium ions derived from reaction of organic halide compounds, as the first component, with silver salts of non-nucleophilic anions, e.g., SbCl.sub.6.sup.-, SbCl.sub.3.sup.-, SbF.sub.6.sup.-, AsF.sub.6.sup.-, SnCl.sub.5.sup.-, PF.sub.6.sup.-, BF.sub.4.sup.-, CF.sub.3 SO.sub.3.sup.- and ClO.sub.4.sup.-, as the second component, The respective parts of the two-part composition may be applied to matable surfaces which then are contacted to effect rapid bonding cure of the composition.

Abstract: Curable mixtures, containing,(a) at least one bisphenol diglycidyl ether based on bisphenol A, hydrogenated bisphenol A or bisphenol F,(b) as a curing catalyst, a colorless or slightly yellow solution of a metal complex compound of the formula I]Me(H.sub.2 O).sub.x (Lm).sub.y ].sup.2+ (A.sup..crclbar.).sub.2 (I),in whichMe is a divalent metal from the group comprising Zn, Cd, Sn, Pb, Ca or Mg,Lm is a saturated cyclic ether having 5 to 7 ring atoms, a linear or cyclic saturated aliphatic ether compound or a mixture of the ether and the ether compound, the ether and the ether compound having a boiling point of at least 60.degree. C., andA is an anion of the formula BF.sub.4.sup..crclbar., PF.sub.6.sup..crclbar., AsF.sub.6.sup..crclbar. or SbF.sub.6 .sup..crclbar.

Abstract: This invention relates to the use of compositions of the formula: ##STR1## wherein n is 2 to 4 and X is --O--, --S-- or ##STR2## wherein R.sub.1 is an aliphatic or aromatic moiety as a curing agent for epoxy resins to form a thermoset material which has a reduced shrinkage.

Abstract: A method is disclosed for deactivating a hydrocarbyl phosphonium salt catalyst of an epoxy resin fusion reaction. The method involves contacting the hydrocarbyl phosphonium salt catalyst with a sulfonic acid, such as p-toluenesulfonic acid or methane sulfonic acid. The method is particularly suited for deactivation of moisture-resistant phosphonium salts such as methylene bis(triphenyl phosphonium halide)s.

Abstract: This invention relates to heat-hardenable epoxide resin mixtures of at least one 1,2-polyepoxide having more than one 1,2-epoxide group per molecule, at least one cyclic carboxylic acid anhydride and at least one ammonium phosphonate or ammonium phosphate as a hardening catalyst, as well as further optional auxiliaries.

Abstract: A curable epoxide composition comprising an epoxide resin, a triaryl phosphite accelerator and a poly(alkylene oxide) polyamine or an amino alkyl piperazine hardener is disclosed.

Abstract: Condensation polymers of high molecular weight, such as polyesters, polyureas, and polyamides, are usually prepared at temperatures of 200.degree. C. or greater. However, by utilizing the catalyst system of the present invention condensation polymers can be synthesized at much lower temperatures. These catalyst systems are comprised of (1) a silicon-phosphorus composition which contains at least one divalent oxygen atom which is bonded directly to a tetravalent silicon atom and a trivalent or pentavalent phosphorus atom; and (2) at least one acid acceptor. For example, P(OSiR.sub.3).sub.3 wherein R can be an aliphatic or aromatic hydrocarbon radical, can be used in conjunction with a basic solvent as a catalyst system. Polymeric agents having pendant diphenylphosphine dichloride groups can also be used in conjunction with an acid acceptor as a catalyst system.

Abstract: An epoxy resin composition containing a cationic curing agent and a cure-retarding amount of a diarylamine. The diarylamine lengthens the pot life of the epoxy-curing agent composition.

Abstract: A process for the rapid formation of thermoset polymers by polymerizing a mixture of a polyepoxide with a polycarboxylic acid containing an alkali or alkaline earth metal cationic complex catalyst is disclosed.

Abstract: A process for reacting an acidic compound or anhydride with an epoxy-containing compound is disclosed. In a preferred embodiment this process comprises reacting a polyepoxide having more than one vic-epoxy group with a phenol in the presence of a methylene bis(triphenylphosphonium)halide catalyst.

Abstract: A heat stable thermoplastic phenolic resin is prepared by (I) reacting (A) the reaction product of (1) at least one epoxy resin having an average of more than one vicinal epoxy group per molecule such as a diglycidyl ether of bisphenol A with (2) one or more polyhydric phenols such as bisphenol A; and optionally (B) one or more polyhydric phenols such as bisphenol A; with (II) a material having only one vicinal epoxy group per molecule such as the glycidyl ether of t-butyl phenol or mixture of such materials; in the presence of an effective quantity of a suitable catalyst such as ethyltriphenylphosphonium acetate.acetic acid complex.

Abstract: A composition is provided comprising an epoxy resin, a cationic curing agent for the epoxy resin and a surfactant. The surfactant improves the reproducibility of cure rates of the cationic curing agent, particularly when the cationic curing agent is used in the form of an aqueous solution.

Abstract: An advanced epoxy resin is prepared by reacting in the presence of a suitable catalyst such as ethyltriphenyl phosphonium acetate.acetic acid complex (A) a mixture containing (1) a polyglycidyl ether of a material containing at least two aliphatic hydroxyl groups per molecule such as a diglycidyl ether of a polyoxypropylene glycol and (2) a dicarboxylic acid such as malonic acid with (B) a dihydric phenol such as bisphenol A. These advanced epoxy resins are useful in the preparation of automobile paints, exterior coatings for beverage cans, coil coatings and adhesives.

Abstract: Relatively high molecular weight epoxy resins cured with conventional curing agents are disclosed wherein the relatively high molecular weight epoxy resin is prepared in the presence of the curing agents. The resultant cured epoxy resin has an improvement in Tg or toughness and the mixture prior to reaction and curing is much easier to apply as a coating or in the preparation of castings, laminates and the like as compared to applications of mixtures of relatively high molecular weight epoxy resins and the curing agents.

Abstract: Polymerizable compositions contain (A) a cationically polymerizable material, such as an epoxide resin, a phenoplast or a cyclic vinyl ether, (B) a hydroxy compound such as styreneallyl alcohol copolymer, and (c) an aromatic iodosyl salt of formula ##STR1## where R.sup.3 and R.sup.4, which may be the same or different, each represent a monovalent aromatic radical having from 4 to 25 carbon atoms, x denotes 1, 2 or 3, and Z.sup.x- denotes an x-valent anion of a protic acid.Suitable salts of formula II include diphenyliodosyl hexafluorophosphate and tetrafluoroborate. The compositions may be photopolymerized or they may be thermally polymerized in the presence, as catalyst for the iodosyl salt, of a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide or an activated .alpha.-hydroxy compound.The compositions may be used as surface coatings and adhesives, and in the preparation of printing plates, printed circuits and reinforced composites.

Abstract: A process for preparing polyepoxides having a wide molecular weight distribution comprises reacting a liquid polyepoxide and polyhydric phenol in a first step, and reacting the resulting intermediate with additional polyhydric phenol and polyepoxide in one or more additional steps.

Abstract: Compounds with a plurality of oxirane functional groups can be cured to a fixture in less than one minute with a catalyst composition of a trityl or tropylium salt of a non-nucleophillic anion and a suitable solvent. Typical catalyst salts include trityl tetrafluoroborate, trityl hexachloroantimonate and tropylium hexafluorophosphate. The catalyst composition may conveniently be extended with liquid polymeric vehicles and acidic fillers.

Abstract: Cationically polymerizable compounds, for example epoxide compounds, can be polymerized photochemically using a catalyst combination consisting of an aromatic iodonium salt and a ketone of the formula I, II or III ##STR1## in which n is 1 or 2 and Ar, X, X', R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1. In this combination, the ketones act as a co-catalyst and drastically accelerate the photopolymerization, although they are not able to initiate a cationic photopolymerization on their own.

Abstract: Heat-curable compositions exhibiting improved thermal pot life are obtained from epoxy compositions comprising (1) a polyepoxide, (2) an aromatic or aliphatic amine and (3) a trihydrocarbyl sulfonium salt.

Abstract: Heat curable epoxy-styrene compositions exhibiting improved processability, low viscosity, long pot life, and fire retardancy which when cured with a special acid anhydride/onium salt epoxy curing blend in combination with a free-radical catalyst, yield cured products exhibiting improved physical properties, such as increased heat deflection temperature, increased flexural strength and increased flexibility.

Abstract: Epoxy resins are prepared by reacting a mixture of (A) a diglycidyl ether of a dihydric aliphatic material, (B) a polyglycidyl ether of a polyhydric phenol having an average of at least about 2.6 glycidyl ether groups per molecule and optionally (C) a diglycidyl ether of a dihydric phenol with a dihydric phenol in the presence of a catalyst.Coating compositions containing the aforementioned epoxy resins have improved chip resistance, chemical resistance or pencil hardness when cured.

Abstract: The increase in hydrolyzable halide content in the preparation of advanced epoxy resins is decreased by conducting the advancement in the presence of an unsaturated organic compound.

Abstract: Described herein are curable molding compositions comprising an epoxide resin, a polyol and particular catalysts. These compositions have good pot life and cure rapidly.

Abstract: The present invention is directed to an improved process for preparing higher molecular weight polyepoxides from lower molecular weight polyepoxides which comprises reacting (1) a lower molecular weight polyepoxide, (2) a polyhydric compound, (3) an etherification catalyst and (4) dimethylol propionic acid.

Abstract: A process for producing an epoxy-type lacquer, which comprises reacting a liquid epoxy resin having about one bisphenol A skeleton on an average in the molecular chain and derived from bisphenol A and an epihalohydrin, with bisphenol A in the presence of a catalyst in an inert organic solvent to prepare a concentrated solution of an epoxy resin having a number average molecular weight of from 2,000 to 10,000, adding an organic solvent to the concentrated solution to dilute it and maintain it at a temperature lower than that at which the catalyst is active, and mixing the resulting diluted solution with a solution of a resin acting as a curing agent for the epoxy resin. The resulting lacquer is especially useful for coating metallic containers.

Abstract: Advanced epoxy resins are prepared which contain triazine groups or both triazine and oxazoline groups. When cured, these resins have higher heat distortion temperatures and/or higher elongation values than advanced epoxy resins which do not contain triazine groups or triazine and oxazoline groups.

Abstract: Microcapsules with liquid fills containing Lewis acid catalysts, catalyst concentrates comprising slurries of the microcapsules in liquid media, and a method for preparing the microcapsules and concentrates. The catalyst concentrates of the present invention are storage stable both alone and when incorporated in a one-part epoxy formulation.

Abstract: Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium trifluoroacetate catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.

Abstract: Compositions that cure when heated comprise(A) an epoxide resin and(B) an effective amount of(i) a diaryliodosyl salt of formula ##STR1## where R.sup.1 and R.sup.2, which may be the same or different, each represents a monovalent aromatic radical of from 4 to 25 carbon atoms, such as a substituted or unsubstituted phenyl group,M represents a metal or metalloid atom, such as phosphorus or boron,X represents a halogen atom, particularly chlorine or fluorine, andn is 4, 5, or 6, and is greater by one than the valency of M or MX.sub.n.sup.- represents pentafluorohydroxoantimonate, and(ii) a catalyst for the diaryliodosyl salt which is a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide, or an .alpha.-hydroxy compound.Typically, the epoxide resin (A) is a bisphenol A diglycidyl ether, the salt (i) is diphenyliodosyl tetrafluoroborate or hexafluorophosphate, and the catalyst (ii) is cupric acetylacetonate or benzpinacol.

Abstract: Improved thermally-curable adhesive compositions for bonding articles of poly(butylene terephthalate) together or to other articles are disclosed. The adhesive compositions comprise at least one epoxidic prepolymer having two or more epoxy groups, an aromatic halonium complex salt thermal initiator dissolved in a compatibilizing non-epoxidic organic liquid, a copper carboxylate salt cocatalyst, a polyhydric alcohol, and optionally, silica filler. The adhesive compositions when heated, cure to form an adhesive bond between articles of poly(butylene terephthalate) which exhibits a vastly improved bond strength over presently available epoxy adhesive materials.

Abstract: An insulating tape for manufacturing an insulating sleeve for electric conductors, impregnated with a heat-hardening epoxy resin-acid anhydride hardener mixture, contains a self-hardening bonding agent-accelerator composition of an epoxy resin as the bonding agent and a quarternary onium salt as the accelerator. To prevent migration of the charge carriers present in the accelerator, the accelerator further has a group which can react with the bonding agent-impregnating resin mixture. This group causes a fixation of the accelerator in the lattice produced during the hardening.

Abstract: Novel advanced epoxy resins are prepared using phosphine or phosphonium salt initiators bearing at least one hydroxyphenyl or thiophenyl groups. These phosphonium salt initiators are novel compositions of matter. The resulting resins contain reduced quantities of extractable phosphorus containing moieties.

Abstract: The advancement method, i.e., the preparation of epoxide resin mixtures by reaction of compounds containing 2 to 4 phenolic hydroxyl groups with a stoichiometric excess of polyepoxide compounds in the presence of a catalyst, comprises adding glycidol as a chain stopper. The products are used in various industrial fields, for example in surface protection.

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: A thermosetting resin composition comprising (A) at least one polyfunctional epoxy compound and (B) at least one polyfunctional nitrile compound and a prepolymer thereof can give a cured product having excellent heat resistance and mechanical properties such as flexibility.

Abstract: Curable compositions of matter comprising an epoxy resin and a curing agent selected from the group consisting of polyvalent metal salts of a phosphorodithioic acid, the acid being derived from the reaction of a phosphorus sulfide with a hydroxyl containing aromatic compound, and products derived from the reaction of the polyvalent metal salt with a mono- or polyamine.

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: Single package, thermosetting epoxy resin-based coating compositions are provided which contain a polyepoxide and a curing agent system therefor which comprises an aromatic urea. At composition curing times and temperatures, the aromatic urea reacts with a portion of the polyepoxide to thereby form in situ a primary or secondary amine which can then function as a coreactive curing agent to complete the cure of the epoxy resin coating.

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: A high heat resistant transparency of epoxy resins cured with adducts of trimethoxyboroxine and benzyl alcohol is disclosed to resist intense heat for these transparencies in their use on military and industrial hardware. This transparency may exist in a composite with other layers of transparent material known to those skilled in the art. The epoxy transparency layer is bound to the other transparent layers, in a variety of configurations, using an interlayer of mercaptan terminated resins. These resins greatly improve resistance to moisture permeability in and about the edges of the entire transparency.

Abstract: A curable resin is composed ofA. an epoxy resin andB. a pyrylium salt as a catalyst, with or withoutC. a metal chelate or metal salt as a co-catalyst.Preferred pyrylium salts are those of the formula ##STR1## Preferred co-catalysts are acetylacetonates, stearates, benzoates, naphthenates, octoates or phthalates of Cu.sup.++, Co.sup.++, Co.sup.+++, Fe.sup.+++ or Al.sup.+++. The resin compositions may be used to produce coatings and moldings.

Abstract: Tetrahydrocarbyl phosphonium bicarbonate salts are employed as catalysts to promote the reaction between (a) vicinal epoxides and (b) carboxylic acids or anhydrides. These catalysts are particularly useful in the preparation of vinyl ester resins.

Abstract: The invention relates to heat curable epoxy resin compositions consisting of an epoxy resin containing, on average, more than one epoxide group per molecule, an aromatic onium salt as catalyst, a copper complex compound as co-catalyst, and a light stabilizer. These compositions are less sensitive to UV irradiation and have a good shelf life at room temperature as well as a good high temperature reactivity.

Abstract: New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4,R denotes an aliphatic, cycloaliphatic, or aromatic group,R.sup.6 denotes H, an alkyl or aralkyl group, or a group --COR.sup.9, --CO--NH--(CO).sub.r --R.sup.10, or --SO.sub.2 --R.sup.11, where r is zero or 1,one, but not both, of R and R.sup.6 denoting an aromatic group,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9, R.sup.10, and R.sup.11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms,t is 1, 2, or 3, andZ.sup.- denotes a t-valent anion of a protic acid.The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat.

Abstract: An improved process for curing a polyepoxide composition with a polycarboxylic acid or polycarboxylic acid anhydride is described wherein the addition of a diphenyliodonium salt accelerator provides for shortened curing reaction times at lower reaction temperatures or at room temperatures if the composition is exposed to a source of ultraviolet radiation.

Abstract: The present invention provides a curable composition comprising (1) at least one epoxy compound containing at least one vicinal-epoxy group and (2) at least one catalyst selected from lithium or Group II metal salts of a non-nucleophilic acid. The present invention further provides an active epoxy curing catalyst composition.

Abstract: Cationically polymerizable compounds, in particular epoxy compounds, can be polymerized by heating in the presence of a catalyst and a co-catalyst. The catalyst employed is a quaternary ammonium salt of an aromatic-heterocyclic compound which contains 1 or 2 N-atoms, and a complex halide anion, e.g. PF.sub.6.sup..crclbar.. The co-catalyst employed is a diaryl ethane derivative, preferably benzpinacol, a silyl oligomer thereof, an organic per compound or a quinone.

Abstract: High temperature-resistant thermobarriers have a filler therein. The filler can be an opaque thermobarrier material, a fabric or cloth such that a laminated thermobarrier is formed, or preformed bubbles of glass, ceramic or plastic such that a syntactic foam thermobarrier is formed. The thermobarrier contains a boroxine compound therein as well as epoxy resins and various phosphorus compounds and/or aromatic alcohols. Generally, the syntactic foam thermobarriers give the best heat protection.

Abstract: Advancement catalysts selected from the group consisting of formylmethylenetriphenylphosphorane and its phosphonium halide salt precursors, e.g., formylmethyltriphenylphosphonium chloride, confer high reactivity and selectivity on epoxy resin advancement reactions. Advanced epoxy resins are useful in the perparation of coatings of high quality.

Abstract: Certain classes of aromatic sulfoxonium salts, such as dimethylphenacylsulfoxonium and acetanilinodimethylsulfoxonium hexafluorophosphates, have little or no effect on prolonged heating with O-glycidyl group-containing epoxides. It has now been found that if a quinone, peroxide, or iodoso aromatic compound is also added, the sulfoxonium salts rapidly bring about the polymerization of such epoxides and curing of such polyepoxides.