Abstract: Novel thermosetting resin compositions comprise a mixture of the epoxyalkylether of a 1,6-diaza[4.4]spirodilactam having a hydroxyaryl substituent on each of the spiro ring nitrogen atoms, and at least one diamine compound. The cured compositions obtained by heating the resin compositions to an elevated temperature have relatively high glass transition temperatures and good physical properties.

Abstract: Polythiols prepared by the reaction of hydrogen sulfide or organic dithiols with polyglycidyl substituted amines have been found to be outstanding curing agents for epoxy resins. Epoxy resins cured with these polythiols are characterized by not only improved gel times, but also improved cure rates, better heat resistance and greater resistance to absorption of water.A useful polythiol is the reaction product of N,N,N',N'-tetraglycidyl-m-xylylenediamine with hydrogen sulfide.

Abstract: Anthraquinones of formula I ##STR1## wherein X is the group --CR.sup.2 R.sup.3 --, where R.sup.2 is H, --CH or C.sub.1 -C.sub.5 -alkyl and R.sup.3 is H or --CN, R.sup.1 is H or C.sub.1 -C.sub.5 -alkyl and R is a direct bond or linear or branched C.sub.1 -C.sub.18 -alkylene which, alone or together with the --CR.sup.2 R.sup.3 -- group, can be interrupted by one or more --O-- when R.sup.2 and/or R.sup.3 are not --CN, and curable compositions comprising (a) an epoxy resin, (b) a hardener if necessary, (c) an anthraquinone of formula I and (d) an amino alcohol. The cured compositions are photosensitive and are suitable for the preparation of coatings and metallic images by electroless metal deposition.

Abstract: A tough, durable, high temperature epoxy tooling composition for making cast-to-size forming tools. The composition comprises a bisphenol-A epoxy, a trifunctional aromatic epoxy, an anhydride catalyst, and an imidazole catalyst. The composition may optionally contain a filler system comprising filler particles having different diameters that are interstitially-matched.

Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.

Abstract: The present invention provides an epoxy resin of the formula ##STR1## where A is selected from the group consisting of --C(CH.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, --S--, --SO.sub.2 --, --CH.sub.2 --, --CO--, --O--, and --C.sub.3 H.sub.6 --, and each B.sub.1, B.sub.2, B.sub.3, and B.sub.4 is independently selected from the group consisting of --H, --F, --Cl, --Br, --I, --CH.sub.2 CH.dbd.CH.sub.2, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, and --C.sub.4 H.sub.9.The present invention also provides a curable composition comprising an epoxy resin of the foregoing formula (I) and an effective curing amount of a hardener for an epoxy resin. The moisture sensitivity of the cured castings and/or composites based on the epoxy resins is lower than known epoxy resin castings and/or composites that have comparable thermal stability, modulus, strength, processability, and toughness.

Abstract: A low viscosity epoxy resin, i.e., a low viscosity polyglycidyl derivative, of an aminophenol having at least one alkyl group on its aromatic ring of which viscosity is 15 poises or below as measured at 25.degree. C., a resin composition containing said resin, and a fiber-reinforced composite material containing as matrix a cured product of said epoxy resin composition and a fiber as reinforcing material.

Abstract: A hydrophilic, substantially epoxy-free self-cross-linkable polymer contains hydroxyalkyl carbamate groups and one or more tertiary amine groups. The polymer suitably is made by reacting an epoxy resin having an average epoxy equivalent weight of from about 100 to about 700 with one or more amines having at least one secondary amine group and at least one hydroxyalkyl carbamate group or precursor thereof. A coating composition comprises an aqueous medium containing the polymer and, optionally, a cross-linking catalyst. A low temperature-curable coating is attained by utilization of the polymer with a suitable quaternary or ternary compound catalyst.

Abstract: Novel tetraglycidates have the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl of 1 to 8 carbon atoms, perfluoroalkyl, or cycloalkylidene of 5 to 7 carbon atoms. Epoxy 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: Water-soluble sulfonium salts are converted, without the elimination of odorous volatile by-products, to water-insoluble products useful as binders in coating formulations by heating a water-soluble cyclic sulfonium salt in which the sulfonium sulfur is bonded only to aliphatic carbons.

Abstract: An epoxy resin composition comprising an epoxy resin that is liquid at room temperature and containing on average more than one epoxy group per molecule and a quarternary piperidinium salt as advancement catalyst.When advanced with compounds having two phenolic hydroxyl groups, such compositions give excellent products of low viscosity which are suitable, for example, for use in powder coating compositions.

Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).

Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electrodeposition are prepared from the product obtained by the process.

Abstract: A low viscosity product is obtained when an adduct is prepared by reacting (A) at least one polyglycidyl ether of a compound containing an average of more than one phenolic hydroxy group per molecule and (B) at least one aliphatic monocarboxylic acid containing 7 to 15 carbon atoms per molecule; wherein components (A) and (B) are present in amounts which provide a ratio of carboxylic acid groups per epoxide group of from about 0.01:1 to about 0.2:1.

Abstract: An epoxy resin composition comprising (A) an epoxy resin having three or more epoxy groups per a molecule and (B) a reactive oligomer having in its molecule an aromatic residue connected thereto by --O-- or --S-- linkage and having at the terminal of the molecule a phonolic hydroxyl group.

Abstract: Novel sulfur containing polyarylene polyether oligomers are disclosed. The oligomers are prepared through condensing salts of hydroxy and/or thio aromatic compounds, halobenzenoid compounds bearing two replaceable halogens and metal or ammonium sulfides following by end capping the resultant oligomer intermediate with a salt of a hydroxy and/or thio aromatic compound.

Abstract: Co-advanced epoxy resins prepared by the reaction of polyethers of polyhydric phenols, diglycidyl ethers of di-secondary alcohols and dihydric phenols, said co-advanced resins being heat curable with suitable curing agents to afford cured coating compositions exhibiting a variety of excellent physical properties and performance characteristics.The diglycidyl ethers have the following formula: ##STR1## as defined in the specification.

Abstract: The invention relates to epoxy resins which can be cured at ambient or slightly elevated temperature. The compositions can be used as adhesives and also as structural material. The epoxy resins of the invention retain advantageous characteristics at elevated temperatures, up to about 120.degree. C. The compositions are advantageously supplied as two-pack kits which are contacted with each other when the epoxy resin is to be used. The first component is a mixture of at least two epoxides; the second component is a curing system which contains at least two amines.The components are:A. epoxies:(1) a tetraglycidyl diamino-diaromatic alkane(2) a triglycidyl ether of an amino aromatic alkaneB. amines:(1) a polyalkylene polyamine(2) an amino-terminated or carboxy terminated alkadiene rubber compound.

Abstract: Cyanobisphenols of the formula: ##STR1## and their diglycidyl ethers may form linear thermoplastic polymers with low oxygen permeability and which contain cyano moieties that may subsequently be reacted to form useful active sites on the polymer.

Abstract: Novel 3-ring tetraglycidates having the formula ##STR1## wherein ##STR2## Y=halogen, C.sub.1 -C.sub.4 alkyl; and n=0 to 4, are disclosed.Epoxy 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: Compounds of formula I or II ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, alkyl, cyclohexyl, phenyl, benzyl or tolyl, or are a --CH.sub.2 --CHR.sup.3 --CH.sub.2 --S--CO--R.sup.4 radical, R.sup.3 is hydrogen or methyl, R.sup.4 is alkyl, cyclohexyl, phenyl, benzyl or tolyl, X is alkylene, --S--, --SO--, --SO.sub.2 -- or substituted alkylene, in which R.sup.5 and R.sup.6 are hydrogen or alkyl, and n is an integer from 1 to 10, can be used as latent hardeners for epoxy resins.The compositions containing epoxy resins and these hardeners are particularly suitable for use as single component adhesive formulations. The cured products have good hot water resistance.

Abstract: This invention is directed to the use of particularly defined epoxy-amine compositions as a protective coating on metals which are exposed to a high temperature, corrosive environment. The metal may be that employed in motor vehicle exhaust system components, such as mufflers and tailpipes. The epoxy-amine compositions comprises epoxy resin component, aromatic amine component, optionally, acid component selected from polycarboxylic acid and anhydrides thereof and optionally, polyol component.

Abstract: Solid epoxy resins having low melt viscosity and high softening points are prepared by partially reacting the aliphatic secondary hydroxyl groups with a monoisocyanate to form pendant urethane groups. These resins are particularly useful as binders in preparing high flow-out, non-sintering powder paints.

Abstract: Compounds of formula I or II ##STR1## in which formulae R.sup.1 and R.sup.2 are each independently of the other hydrogen, alkyl, alkenylmethyl, cyclohexyl, phenyl, benzyl or tolyl, or are a --CH.sub.2 --CHR.sup.3 --CH.sub.2 --S--H group, R.sup.3 and R.sup.4 are each independently of the other hydrogen or methyl, X is alkylene, --S--, --SO--, --SO.sub.2 -- or substituted alkylene, R.sup.5 and R.sup.6 are each independently of the other hydrogen or alkyl, R.sup.8 is hydrogen, alkyl, alkenylmethyl or phenyl, and wherein n is an integer from 1 to 10, can be used as hardeners for epoxy resins.The compositions containing epoxy resins and these hardeners are particularly suitable for use as adhesive formulations. The cured products have good moisture resistance.

Abstract: This invention relates to an aqueous, acidic composition useful to deposit a corrosion inhibiting and adhesion promoting coating on a metal substrate and a method for doing same. The composition has a pH of between about 2 and about 6 and comprises water-soluble or water-dispersible metal-chelating o-hydroxybenzylamine compound, wherein the amine moiety contains pendant ethanol or propanol moiety.

Abstract: This invention relates to an aqueous composition useful to deposit a corrosion inhibiting and adhesion promoting coating on a corrodible metal substrate and a method for doing same. The composition has a pH of between about 2 and about 10 and comprises water-soluble or water-dispersible metal-chelating diphenolamine compounds.

Abstract: The invention relates to compounds of the formula I ##STR1## in which A is a group ##STR2## R.sup.1 is hydrogen or methyl R.sup.2 is C.sub.1 -C.sub.6 -alkyl, halogen or phenyl,X is a direct C--C bond, --CH.sub.2 -- or --SO.sub.2 --,m is 0, 1, 2 or 3, n is 0, 1 or 2 andp is 0 or, in the case of X=--CH.sub.2 --, can also be an integer from 1 to 6, with the proviso that the groups --A and --O--A are in the ortho-position relative to one another.The compounds can preferably be used as matrix resins for composite materials.The invention also relates to the allyl glycidyl ether intermediates, from which the compounds of the formula I are as a rule prepared by epoxidation with peracids.

Abstract: The invention relates to water-dispersible binders which are intended for cationic electropaints and are based on reaction products which are formed from modified epoxy resins and primary and/or secondary amines and which can, if desired, also contain crosslinking agents, pigments, flow-control agents and other customary auxiliaries. They contain as reaction products those which have been prepared by reacting(A) low molecular weight epoxy resins which contain epoxy compound aromatic groups and have an epoxide equivalent weight of less than 375 with(B) aliphatic and/or alicyclic polyfunctional alcohols having hydroxyl groups or carboxylic acids having carboxylic groups and both having a molecular weight of less than 350 and addition of the hydroxyl groups and carboxylic groups to the epoxy groups of (A) in such a way that the reaction products of (A) and (B) contain 10-45% of aromatic groups, calculated as the phenylene group, and have terminal epoxy groups.

Abstract: The present invention relates to a new thermoplastic polymer composition having the processing characteristics of a thermosetting polymer along with an improved balance of properties including solvent resistance and improved modulus/glass transition temperature/toughness balance. These new polymer compositions are prepared by reacting certain diphenolic compounds with certain diepoxide compounds to form linear units which are lightly crosslinked through the resulting secondary hydroxyl groups. Also disclosed and claimed are processes for preparing such compositions, cured compositions and end-use applications.

Abstract: Polycyanate esters of polyhydric phenols are cured with a liquid solution of a metal acetylacetonate in an alkylphenol. Such cured compositions are useful in structural composites, transfer molded-encapsulants, filmed structural adhesives and printed wiring boards.

Abstract: An improvement in curable compositions which comprise a polyglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and a halogenated dihydric phenol such as tetrabromobisphenol A, the improvement being employing as the halogenated dihydric phenol one in which the halogen atoms are meta with respect to the hydroxyl groups such as 2,2',6,6'-tetrabromo-3 ,3',5,5'-tetramethyl-4,4'-biphenol. These compositions can be cured by heating in the presence or absence of a 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: Homogeneous thermoset terpolymers which may be used in the preparation of laminates for circuitry boards will comprise a diepoxide of a polyether of a polyphenol, a dicyanate ester of a polyether of a polyphenol and an alkenyl aryl compound. The polymers are prepared by admixing a solution of the diepoxide of a polyether of a polyphenol and an alkenyl aryl compound with a second solution of the dicyanate ester of a polyether of a polyphenol and the alkenyl aryl compound at elevated temperatures. The resulting terpolymer will possess desirable characteristics such as high glass transition temperature and low dielectric constant.

Abstract: High temperature resistant molding materials containing(A) 5-95 mol % of blocks having the structural unit I ##STR1## (B) 5-95 mol % of blocks having the structural unit II ##STR2## (C) 0-80 mol % of blocks having the structural unit III ##STR3## the molecular weight of the blocks being within the range 2000-20,000, where X is --O--, --S--, ##STR4## (only if a or b.noteq.0), ##STR5## (R.sup.7 =R.sup.8 =CH.sub.3 only if a or b.noteq.O) or a chemical bond, R.sup.7 and R.sup.8 are each alkoxy or alkyl of 1-6 carbon atoms, aryl or hydrogen, Q and W are each ##STR6## Z is --O-- or a chemical bond and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each alkyl or alkoxy of 1-6 carbon atoms, aryl, Cl or F and p, q and r are each 0 or 1 and a, b, c, d and e are each 0, 1, 2, 3 or 4.

Abstract: Novel compositions suitable for use in preparing prepregs comprise an epoxy resin and a poly(hydrocarbylthio)aromatic diamine curing agent, preferably a substituted di(alkylthio)-diaminobenzene wherein the alkylthio groups contain 1-10 carbons.

Abstract: Epoxy resins are prepared by (a) adding an alkali metal hydroxide solution to a mixture containing an excess of an epihalohydrin, a phenolic hydroxyl-containing or an aromatic amine-containing compound and an organic solvent which codistills with water and the epihalohydrin, (b) conducting the reaction under reduced pressure while continuously removing water by codistillation, (c) separating the water from the distillate and returning the epihalohydrin and organic solvent to the reaction mixture, (d) drying the reaction mixture, (e) removing insoluble materials by suitable mechanical separation means, (f) washing the resin/epihalohydrin/organic solvent mixture with water so as to substantially remove water soluble materials, (g) drying the epihalohydrin/resin mixture, and (h) recovering the resultant epoxy resin from the resin/epihalohydrin/organic solvent mixture by any suitable means. This process produces an epoxy resin which is low in hydrolyzable halide and total halide.

Abstract: New and improved heat curable compositions are disclosed comprising epoxidic prepolymers and mono- and di-imidazole-carboxamides. The compositions are stable at room temperature, but cure readily at moderate temperatures of substantially less than about 250.degree. F., preferably at about 180.degree. F. to about 200.degree. F. and especially preferably at about 160.degree. F. to about 180.degree. F. The cured neat resins are useful as adhesives and as matrix resins in reinforced composites, with excellent physical properties.

Abstract: Disclosed herein is a low molecular weight epoxy-functional polyurethane and high solids thermosetting coating compositions prepared therewith.

Abstract: A moisture curable composition contains:(a) one or more episulfide compounds having on the average more than one 1,2-epithiopropyl ether group of the formula I ##STR1## per molecule, and (b) one or more aliphatic N,N'-dialkyl-substituted diketimines of the general formula II ##STR2## wherein A is a divalent aliphatic, cycloaliphatic or arylaliphatic group, andR.sup.1 and R.sup.2 are each an alkyl group, or form together with the C-atom, to which they are bonded, a cycloalkyl group or cycloalkenyl group, and(c) at least one component, selected from the group of the setting accelerators as well as commercially available solvents, reactive diluents, plasticizers, thixotropic aids, fillers and pigments.This composition may be used as lacquers, paints and coatings for steel and concrete.There is also described a process for the preparation of 1,2-epithiopropyl ethers.

Abstract: Advanced epoxy resins prepared by the reaction of diglycidyl ethers of di-secondary alcohols and dihydric phenols, said advanced resins being heat curable with suitable curing agents to afford cured coating compositions exhibiting a variety of excellent physical properties and performance characteristics.

Abstract: An epoxy resin curing composition comprising a novel curing agent which is obtained by the amidation with elimination of alcohol between an adduct of a carboxyl-containing acrylonitrile-butadiene copolymer with an epoxidized fatty acid ester and an amide-forming nitrogenous compound. This composition exhibits improved adhesion involving peel strength to plastics, rubbers or flexible vinyl chloride resins and is excellent in mechanical strength and resistance to water and alkali and particularly to acid.

Abstract: A tough, durable, high temperature epoxy tooling composition for making cast-to-size forming tools. The composition comprises a bisphenol-A epoxy, a trifunctional aromatic epoxy, an anhydride catalyst, and an imidazole catalyst. The composition may optionally contain a filler system comprising filler particles having different diameters that are interstitially-matched.

Abstract: Coating compositions which are capable of curing at room temperature comprise (i) a condensation polymer in which the polymer backbone contains at least one grouping of the formula --CO--C(R).dbd.C(R)--CO--, where R is hydrogen, a halogen or an alkyl or aryl group, and (ii) a compound carrying at least three primary amine or thiol groups. The compositions are of particular interest as undercoats in the automobile refinish trade.

Abstract: Halogenated aromatic epoxy resins are disclosed wherein the halogen atoms are in the meta position with respect to a glycidyl ether group attached to an aromatic ring.Advanced epoxy resins are disclosed which result from the reaction of a relatively low molecular weight epoxy resin and a polyhydric phenol wherein at least one of the reactants contains at least one halogen atom which is meta with respect to a glycidyl ether group or a hydroxyl group attached to an aromatic ring. These advanced epoxy resins, when cured with a suitable curing agent, possess an improvement as compared to an advanced epoxy resin containing halogen atoms which are ortho with respect to a glycidyl ether group in at least one of thermal stability, glass transition temperature, relationship of viscosity to molecular weight and resistance to forming hydrolyzed halides in the presence of a refluxing solution of an alkali metal hydroxide.

Abstract: Modified cationic epoxy resins wherein phenols linked through modified urea groups are used to extend the chain of diepoxy resins are described. The modified cationic resins can be formulated as paints which exhibit excellent properties particularly when used for electrodeposition paints.

Abstract: Epoxy resins containing both terminal hydroxyl groups and epoxy or epoxy-derived groups are prepared by advancing a polyepoxide with a polyol and terminating the reaction at a point such that the epoxy resin reaction product contains both epoxy and terminal hydroxyl groups. The controlled conversion resins have improved cure rates. The epoxy groups can be further reacted to form epoxy-derived groups to improve the cure rate even further. The epoxy resins exhibit lower melt and solution viscosities than those exhibited by conventional epoxy resins having the same epoxy equivalent weight, as well as curing quickly when used. The resins are usefully employed at high solids levels in can coating formulations and other epoxy formulations wherein the resin is applied from an organic liquid solution or aqueous dispersion.

Abstract: Mannich condensates are prepared from 2,6-di-t-butylphenol, formaldehyde and a polyoxyalkylene amine. The novel compounds are useful as epoxy accelerators and curing agents.

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: A thermosettable heat-resistant resin composition containing (A) an amino group-terminated imide compound produced by imidating an aromatic diamine with an aromatic tetracarboxylic anhydride at a diamine:anhydride molar ratio of from 1.2:1 to 4:1, and (B) an epoxy resin having at least two epoxy groups, the molar ratio of the amino group of the imide compound to the epoxy group of the epoxy resin being 1:1.6 to 1:2.6.

Abstract: The present invention is directed to polyurethane compositions containing triazine or both triazine and oxazoline or imino carbamate groups which are prepared by reacting:1.(a) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group, or(b) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one oxazoline group, or(c) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one imino carbamate group, or(d) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one other N-heterocyclic group, or(e) a mixture of the above and2. at least one material having more than one isocyanate group per moleculewherein the components are employed in proportions which provide a ratio of isocyanate groups to hydroxy groups of from about 0.05:1.0 to about 10.0:1.0, preferably from about 0.95:1.0 to about 1.5:1.0.

Abstract: Curable thermosetting resin compositions comprising at least one cycloaliphatic epoxy resin having at least two 1,2-epoxy groups per molecule, and certain aromatic diamines having three aromatic rings in the molecule are disclosed. Resin compositions comprised of, for example, bis(2,3-epoxycyclopentyl)ether and 1,3-bis(4-aminophenoxy)benzene exhibit a highly desirable balance of physical and chemical properties which renders such compositions ideally suited for use in the fabrication of wet winding composites. The resin compositions prepared in accordance with the invention have unexpectedly low viscosity, high glass transition temperatures, high tensile properties and unexpectedly low water uptake. Accordingly, the resin compositions find particular application in the preparation of composites by wet winding procedures.