Abstract: Novel 3-ring tetraglycidates having the formula ##STR1## wherein X=O, S, ##STR2## --CH.sub.2 --, C.dbd.O; Y=halogen, C.sub.1 -C.sub.4 alkyl; and p0 n=0 to 4, are disclosedEpoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.

Abstract: Aromatic amines and their alkyl, amide, imide or amide-imide substituted derivatives in the presence of catalytic quantities of phenols, cresols, xylenols, bisphenols, and their like cause epoxide resins to thermoset at ambient temperatures. The resulting crosslinked polymers are useful for two component solution systems which provide corrosion and temperature resistant clear coatings or paints, and can also be used as solventless, liquid, two component systems for casting clear, pigmented or filled parts.

Abstract: A curable epoxy resin mixture containing an adduct of an epoxy resin with a bifunctional phenol or a bifunctional aromatic carboxylic acid of the formula ##STR1## where A=SO.sub.2 or CO, Ar is ##STR2## and X is OH or COOH, and an aromatic amine as a curing agent.

Abstract: Hydroxyaromatic oligomers are prepared by (I) reacting (A) an aromatic hydroxyl-containing material such as bisphenol A with (B) a cyanogen halide such as cyanogen bromide in the presence of a base such as triethylamine and (II) co-oligomerizing the cyanate-containing product from (I) with (C) a polymaleimide such as the reaction product of maleic anhydride with methylenedianiline optionally in the presence of (D) a co-oligomerization catalyst such as cobalt naphthenate. These oligomers are useful in the preparation of epoxy resins.

Abstract: Vinyl ester resins are prepared by reacting a polyepoxide of a co-oligomerization product of a mixed cyanate of a polyphenol and a polymaleimide with a monounsaturated monocarboxylic acid.

Abstract: This application discloses a synthetic resin based on alcohol-modified polyepoxides. The synthetic resin can be prepared by reacting a diepoxide, or a mixture of diepoxides, having an epoxide equivalent weight of less than about 500, with compounds with a hydroxyl group, which is reactive towards epoxide groups, in a molar ratio from about 2:1 to about 7:6 at temperatures from about 100.degree. C. to about 180.degree. C. in an organic solvent free of hydroxyl groups. The synthetic resin has terminal epoxide groups and a mean molecular weight from about 400 to about 5000.

Abstract: Imide functional polyphenols are prepared by reacting an excess of a phenol with an unsaturated diimide which is prepared by reacting an unsaturated polycycloaliphatic dicarboxylic acid anhydride with a diamine.These materials are useful in the preparation of castings, coatings, laminates and the like.

Abstract: Heat-curable compositions are described, comprising(a) an epoxide resin and(b) an effective amount of a urea of formulaAr--NHCON(R.sup.3)R.sup.4whereAr represents an aromatic group linked through an aromatic carbon atom to the indicated nitrogen atom and which is substituted by an amido group, andR.sup.3 and R.sup.4 each represent an aliphatic, cycloaliphatic, or araliphatic hydrocarbyl group, optionally substituted by a halogen atom or a hydroxyl group, or R.sup.3 may further represent a hydrogen atom, or R.sup.3 nd R.sup.4, together with the indicated nitrogen atom, may represent a heterocyclic ring of 3 to 5 carbon atoms which may also have one oxygen atom in the ring.Such amidoarylureas may be used alone with the epoxide resin, or in combination with an accelerator for the heat-curing reaction, selected from dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines, imidazoles, and carboxylic acid-tertiary amine salts.

Abstract: New and improved heat curable compositions are disclosed comprising epoxidic resin(s) and aromatic ether-sulfone polyamines, alone or in combination with other diamine curing agents and/or curing catalysts alone, or in further combination with reinforcements, e.g., graphite fibers and, optionally modified with second resins. The cured neat resins and fiber resin matrix compositions exhibit high toughness, compression strength and short beam shear strength under dry, wet and hot/wet conditions.

Abstract: Multifunctional epoxy resins are prepared by reacting (1) a polyglycidyl ether of a polyhydroxyl-containing material said glycidyl ether having an average of at least 0.

Abstract: The invention discloses a polyfunctional imide-containing phenolic imide which is the reaction product of a polyanhydride having at least three anhydride groups and aromatic compound having a single aromatic primary amine group. A varnish is prepared by the addition of an epoxy crosslinking agent to the imide. Fibrous substrates can be impregnated with the varnish and partially cured to prepare prepregs, and stacks of prepregs can then be heated and pressed to prepare laminates or printed circuit boards.

Abstract: Novel phosphorus-containing polyglycidyl ethers capable of forming a cured epoxy resin having a high flame retardancy and excellent in heat resistance characteristics such as heat deterioration resistance, glass transition temperature, thermal deformation temperature and the like; a process for producing said phosphorus-containing polyglycidyl ethers; phosphorus-containing polyphenol compounds used in production of said phosphorus-containing polyglycidyl ethers; and a process for producing said phosphorus-containing polyphenol compounds.

Abstract: A bisorthodinitrile monomer having the formula: ##STR1## and an epoxy monomer having the formula:R--O--A--O--Rare mixed with or without an amine curing agent and heated to a temperature ufficient to induce polymerization. The resulting epoxy-phthalonitrile copolymer has improved properties relative to the epoxy polymers including higher thermal and oxidative stability, higher glass transition temperature, better shelf life, lower water absorptivity, and better electrical properties. The properties of the epoxy-phthalonitrile copolymer can be varied by varying the epoxy:phthalonitrile ratio.

Abstract: A process for preparing a phosphate ester which contains at least one terminal epoxide moiety, the process comprising contacting under reaction conditions, optionally in the presence of water, at least one phosphoric acid ester with an amount of an epoxide having an epoxy equivalent greater than one. The product compositions can be cured by standard epoxide curing agents to provide protective coatings having intumescent properties.

Abstract: Thermosettable compositions are prepared which contain (A) from about 0.1 to 100 percent by weight of an esterified aromatic cyanate; (B) from zero to about 99.9 percent by weight of an aromatic polycyanate, an aromatic polycyanamide or mixture thereof and (C) from zero to about 99.9 percent by weight of an epoxy resin.

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: This invention is directed to hydroxyl terminated azomethines formed by reacting aromatic hydroxyl aldehydes or ketone compounds with diamines. These azomethines may be reacted with epoxy resin to produce polymeric material having high glass transition temperatures.

Abstract: The invention relates to water-dispersible binders for cationic electro-dip paints with a base of modified epoxy resins. The binders are produced by reaction of(A) epoxy resins having a molecular weight of at least 350 with(B) elasticized polyphenols having a molecular weight of over 350 with addition to the epoxide groups and further reaction of the reaction product of (A) and (B) with(C) primary and/or secondary amines or ammonium salts to obtain the required water-dispersibility.

Abstract: This invention is directed to hydroxyl terminated azomethines formed by reacting aromatic dialdehydes or aromatic diketones with hdyroxyl-amino compounds. These azomethines may be reacted with epoxy resin to produce polymeric material having high glass transition temperatures.

Abstract: 100 percent solids epoxy, nitrile coating compositions comprising:(a) epoxy resins, and(b) epoxy-nitrile monomers which are useful for protective coatings.The invention further includes a process for producing the 100 percent solids epoxy nitrile coating compositions comprising:(1) forming a mixture of the epoxy resins with the epoxy nitrile monomers and curing agents,(2) applying the mixture to a substrate to form a coating, and(3) curing the coating so that in situ copolymerization of the epoxy resin and epoxy-nitrile monomer results in a multifunctional epoxy nitrile coating system.

Abstract: Curable compositions are disclosed which comprise a polyglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and a halogenated dihydric phenol such as tetrabromobisphenol A. These compositions can be cured by heating in the presence or absence of catalyst for reacting epoxy groups with phenolic hydroxyl groups such as 2-methyl imidazole. These compositions are particularly useful in the preparation of electrical laminates.

Abstract: Heat-curable mixtures, containing (a) an epoxide resin having on average more than one epoxide group in the molecule, (b) an allyl-substituted or methallyl-substituted imide of the formula I ##STR1## in which E is allyl or methallyl, G is hydrogen or methyl, n is 1 or 2, and R is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, benzyl or arylene, and (c) a curing catalyst, have good storage stability and processability and produce moulded materials having high mechanical strength values and good resistance to heat.

Abstract: Diurethane diureas of the formula ##STR1## wherein each R is a radical derived from a diisocyanate and having at most 20 C atoms, R' is a radical derived from a diol and having a molecular weight of at most 1500, and the radicals R" are each methyl or ethyl, or both radicals R" bound to the same N atom form together with the N atom the piperidino, morpholino or pyrrolidino radical, are valuable curing agents for epoxide resins, and are also suitable as accelerators for the hot-curing of epoxide resins with dicyandiamide, cyanoacetyl compounds and polycarboxylic acid anhydrides.

Abstract: Triglycidyl compounds of the formula I ##STR1## and epoxy resin mixtures containing a triglycidyl compound of the formula I and a tetraglycidyl compound of the formula II ##STR2## in which formulae each of R and R' independently is a hydrogen atom, C.sub.1 -C.sub.6 alkyl, phenyl, cyclohexyl or cyclopentyl, and each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently is a hydrogen atom, a halogen atom, or C.sub.1 -C.sub.6 alkyl.Thses compounds are valuable epoxy resins which are also suitable for the preparation of B-stage resins.

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: 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: 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 thermosettable compositions comprising a mixed cyanate of a polyphenol containing a copolymer of an ethylenically unsaturated compound and an alkenylphenyl cyanate are disclosed. These compositions are also useful in the preparation of novel epoxy resin 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: Aromatic N-glycidylamines are prepared by treatment of an amine having at least one, and preferably two or more aromatic amino hydrogen atoms, with epichlorohydrin in the presence, as catalyst, of a di- or higher-valent metal salt of nitric or perchloric acid, or of a carboxylic or sulphonic acid substituted by fluorine, chlorine or bromine on the carbon atom alpha to the carboxylic or sulphonic acid group, and dehydrochlorinating the product. The presence of the metal salt gives a product having a higher glycidyl content and a lower viscosity than does the same reaction in the absence of such a salt.Suitable aromatic amines include aniline, phenylene diamines, phenylene diamines substituted on the aromatic ring and bis(4-aminophenyl)methane. The metal salt may be of, for example, magnesium, calcium, zinc, manganese, nickel, iron, lanthanum, vanadium, ytterbium or uranium.

Abstract: A resinous hardener system comprising the reaction product of diethyl toluene diamine and an epoxide having a functionality of at least two, the hardener being capable of incorporation into a variety of epoxy and urethane resins.

Abstract: A method of making an epoxy prepolymer curing agent is disclosed. The method comprises the steps of reacting a mixture of piperidine and an epoxy resin so as to form an epoxy prepolymer adduct. The adduct is mixed with 2-ethyl-4-methylimidazole thereby forming the curing agent composition.

Abstract: Compounds containing (a) a fluoroaliphaticsulfonamido moiety, and (b) a moiety containing (1) at least two oxirane groups, (2) at least two non-terminal N-.beta.-hydroxyalkylene groups, or (3) at least one oxirane group and at least one non-terminal N-.beta.-hydroxyalkylene group. The compound is capable of being cured with a curing agent to give a cured product having excellent water resistance and oil resistance.

Abstract: 1. An epoxy resin composition is described, comprising(1) a mixture of epoxides of Components (A), (B) and (C)Component (A):20 to 60 wt % of an epoxy compound having a spiroacetal ring represented by the formula: ##STR1## Component (B): 10 to 50 wt % of a brominated epoxy resinComponent (C):10 to 50 wt % of an epoxy resin selected from the group consisting of diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, novolac type epoxy resins and N,N,O-triglycidyl-aminophenol type epoxy resins, and(2) a hardening agent.

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: A polyglycidyl derivative of an aromatic diamine, aminophenol, or polyphenol and a diglycidyl ether of a bisphenol are reacted with a bisphenol, in the presence of a catalyst at elevated temperature, to yield a reaction product wherein each glycidyl group is effectively endcapped with a moiety containing a free hydroxyl group. The ratio of equivalents of polyglycidyl compound to diglycidyl compound is 1 to 4 to 1 to 1, and of bisphenol to total glycidyl compounds is 1.8 to 1 to 2.4 to 1. Said product is useful for curing solid epoxy resins. The epoxy resins cured by said product have a dense crosslinked network resulting in concomitant superior coating properties especially chemical resistance while maintaining good flexibility.

Abstract: A novel composition is described comprising an admixture of an unsaturated polyimide prepolymer essentially free of terminal amine groups and an epoxy resin having a homopolymerization temperature that is greater than the temperature at which the polyimide polymerizes. These compositions maintain the superior glass transition temperatures and moisture resistance of the polyimide while picking up the desirable handling properties of the epoxy. These compositions have excellent high temperature and moisture resistant properties and excellent storage stability. For instance, carbon composites made with these materials have exhibited 60% shear property retention at 450.degree. F. after being boiled in water for one week. Also described are prepregs comprising the novel composition, methods for curing the novel composition to obtain the superior properties, and articles of manufacture comprising the novel composition.

Abstract: Epoxide resins are cured by heating with a hydroxyphenylurea of formula ##STR1## where R.sup.2 denotes --NH.sub.2, --NO.sub.2, --Cl, --Br, or alkyl, p denotes zero, x and y each denote zero or 1, and the sum of x+y is 1. Such hydroxyphenylureas may be used alone, as accelerators for heat-curing with other agents such as dicyandiamide, melamine, and carboxylic acid hydrazides, or may be used as the primary curing agent with promoters such as dicyandiamide, melamine, and carboxylic hydrazides.

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: Epoxy coatings containing polyoxyalkyleneamines provide improved adhesion when applied to minimally cleaned, corroded metal surfaces.

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: The process and polyoxyalkylene compound prepared by reacting a dihydroxydiphenylsulfone with at least one alkylene oxide in the presence of a catalyst.

Abstract: Epoxy resins are prepared by reacting an excess of an epihalohydrin with a phenolic hydroxyl-containing compound in the presence of the incremental addition of a basic catalyst while removing water by codistilling with a solvent and epihalohydrin.

Abstract: Epoxy phosphate-carboxyl copolymers substantially free of epoxy functionality and aqueous coatings containing the same are disclosed. These copolymers are formed by copolymerizing monoethylenically unsaturated monomers, including carboxyl-functional monomer, in an organic solvent solution containing an epoxy-functional epoxy phosphate, there being at least 5% of carboxyl-functional monomer and at least 10% of total monomers present in the copolymer. The copolymer is converted into a water soluble salt with volatile amine and phenoplast resins are preferably used to provide at least part of the curing agent.

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: Epoxy resins containing triazine groups are prepared by (I) reacting (A) a material having at least one aromatic hydroxyl group per molecule such as bisphenol A with (B) a cyanogen halide such as cyanogen bromide in the presence of (C) a base and recovering a mixture of cyanate-containing products and unreacted (A) materials; (II) trimerizing the product recovered in (I) in the presence of a trimerization catalyst such as cobalt naphthenate and (III) epoxidizing the product from step II by reaction with an epihalohydrin such as epichlorohydrin, dehydrohalogenation of the resultant product with a basic acting material such as sodium hydroxide and recovering the resultant epoxy resin containing triazine groups.

Abstract: Epoxy resin compositions are disclosed which are the reaction products resulting from reacting (A) the reaction product of a cyanuric halide and at least one dihydric or polyhydric phenol with (B) at least one dihydric or polyhydric phenol and (C) at least one epoxy resin having an average of more than one epoxy group per molecule. These epoxy resin compositions are suitable for use as electrical laminates, structural laminates, coatings, castings, electrical encapsulation and the like.

Abstract: Phosphorus-containing epoxy resins are prepared by reacting an epoxy resin with a polyhydric phenolic compound and a phosphoramide.

Abstract: New compositions of matter are disclosed which comprise (1) a cyanate-containing polymer or mixture thereof and optionally (2) a polycyanate or mixture thereof and/or (3) an epoxy resin. These compositions are thermosettable upon heating in the presence of suitable curing agents or catalysts.

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.