Abstract: A one-component reactive resin system which is stable in storage but nevertheless can readily be cured completely comprises a mixture of commercially available epoxy resins and phosphorus-containing glycidyl esters, in particular phosphonic acid diglycidyl esters, as well as cationic photoinitiators. The low-viscosity reactive resin systems cannot be cured purely by means of heat and can be processed at high temperatures and in particular can have a high filler content. The reactive resin systems, which are stable to storage even after UV activation, can be cured to flame-resistant molded materials under moderate conditions.

Abstract: Novel polymers of general formula: ##STR1## wherein R is an alkyl or aryl group that contains an active hydrogen atom (as determined by the Zerewitinoff test); A is a spacing group having at least one carbon atom; B is a spacing group having at least two carbon atoms; and R and R' are alkyl or aryl groups. The polymer is synthesized via the Mannich pathway, involving formation of an imine intermediate.

Abstract: An epoxy resin system comprising a) at least one nitrogen containing epoxy compound having at least two epoxy groups, b) at least one phosphorus compound with at least one epoxy group, c) at least one metallic complex compound as curing agent and d) optionally filler and additive substances free of halogenated compounds and having a low degree of inflammability.

Abstract: An acid anhydride-containing one package epoxy resin composition consisting indispensably of (1) an epoxy resin having two or more epoxy groups in one molecule, (2) an acid anhydride, (3) at least one of (a) a liquid latent curing accelerator, (b) a latent curing accelerator soluble in an epoxy resin having two or more epoxy groups in one molecule and (c) a latent curing accelerator soluble in an acid anhydride, and (4) a dispersible latent curing accelerator, wherein the ratio of (1) to (2) is from 0.8 to 1.2, defined as the number of acid anhydride equivalents/the number of epoxy equivalents, and the amounts of (3) and (4) each are from 0.1 to 10 parts by weight to 100 parts by weight of the epoxy resin. The composition has excellent infiltrability, storage stability and reactivity.

Abstract: The present invention provides a process for preparing an epoxy phosphate ester resin, which comprises (1) reacting an epoxy resin having an average of greater than one vicinal epoxy group with a phosphoric acid source material to obtain an epoxy phosphate ester; and (2) further reacting the obtained epoxy phosphate ester with a phosphoric acid source material. The present invention provides epoxy phosphate ester resins obtained by the above process, which exhibit good water-solubility. The coating compositions containing such epoxy phosphate ester resin show good coating properties such as good corrosion resistance, chemical resistance, heat resistance and flexibility.

Abstract: The invention provides epoxy resin compounds for manufacturing prepregs and composite materials, which can be obtained inexpensively and have good processibility, and provide--without having to add flameproofing agents--virtually inflammable molded materials with a high glass transition temperature. The epoxy resin compounds contain the following constituents:(A) an aromatic and/or heterocyclic polyepoxide resin that is free of phosphorous, optionally in a mixture with an aliphatic epoxy resin;(B) an epoxy-group-containing phosphorous compound and(C) an aromatic polyamine as a curing agent.

Abstract: Compositions containing an aryl phosphite and water to hydrolyze the aryl phosphite provide controlled and extended work time when used as hardening agents for the ambient temperature hardening of phenolic resins and for rapid hardening of such resins at modestly elevated temperatures. Pre-solvolysis with small quantities of water, alkanols of 1 to 4 carbon atoms or alkylene glycols of 2 to 4 carbon atoms improve compatibility of trisubstituted phosphites with the resin. Pre-hydrolysis of the phosphites as well as addition of furfuryl alcohol or alkylene glycols of 2 to 4 carbon atoms accelerate the hardening (curing) of the resin. Various compounds such as: carboxylic acid amides, urea, dicyandiamide, N-methylolated amides, N-alkyl 2-pyrrolidinones having 1 to 4 carbon atoms in the alkyl group, those having an internal epoxide group, alkanols, and Schiff bases retard the ambient temperature hardening of the resin with the aryl phosphite hardening agents.

Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.

Abstract: The present invention is directed to epoxy-based polymeric nonlinear optical materials in which a nonlinear optical active moiety or functionality forms the crosslink between polymer chains and a process for making the nonlinear optical (NLO) epoxy polymer including heating an epoxy resin and a curing agent such as a bi- or tri-functional aromatic amine containing an electron-withdrawing group, for example, diamino diphenylsulfone and poling the mixture under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical moieties in the polymer. The polymers have enhanced stability over polymers in which only one end of an NLO active moiety is attached to the polymer chain.

Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.

Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.

Abstract: A halogen free casting resin suitable for covering electron devices with a fire retardant material contains an acidic ester of an hydroxy-functional phosphor compound and an organic anhydride. A stable mixture can be generated from the acidic ester and the hardener component of the casting resin, and further used for the hardening of epoxides resins. The acidic ester is chemically integrated in the epoxide resin matrix in a stable mixture, thereby improving the long term fire-retardancy of the casting resin molding compound without increasing the volatility of the mixture.

Abstract: Compositions are prepared by the reaction of (A) an advanced composition resulting from reacting (1) at least one of (a) at least one epoxidized triglyceride of a fatty acid, or (b) at least one epoxidized fatty acid having an average of more than one unsaturated group per molecule or (c) at least one diepoxyalkane, or (d) any combination of any two or more of (a), (b) or (c), or (e) a combination of any one or more of (a), (b) or (c) and (f) a diglycidyl ether of a dihydric phenol; with (2) a dihydric phenol; (B) optionally a monohydric phenol; (C) a phosphorus-containing compound; and (D) optionally a base. These compositions can be cured with curing agents which react with aliphatic hydroxyl groups.

Abstract: A two component-type curing agent composition is disclosed which comprises a first curing agent which is capable of cross-linking an epoxy resin and which is at least one member selected from primary amines, phenolic compounds and acid anhydrides, and a second curing agent which is at least one compounds represented by the following general formula: ##STR1## wherein X is --CR.sub.1 R.sub.2 --, --CO--, --COO--, --SO.sub.2 --, --SO--, --S--, --O--, --NR.sub.1 --, --SiR.sub.1 R.sub.2 -- or --POR.sub.1 -- where R.sub.1 and R.sub.2 each stands for hydrogen, a lower alkyl or a phenyl; Y and Y' each stands for hydrogen, a lower alkyl or an electron attracting group; R is a lower alkyl; and m and n each is an integer of 1-4.

Abstract: An electrical encapsulation composition containing an epoxy resin, a phenolic curing agent and a tris(dialkoxyphenyl)phosphine high cured glass transition temperature and good crack resistance.

Abstract: This invention relates to the use of phosphorus-containing compounds, specifically cyclic organophosphorus compounds, as carbodiimidization catalysts in the preparation of open-celled flexible polyurethane foam for the purpose of controlling foam density and providing softer foams. foams that are softer and of lower density can be prepared with significantly reduced quantities of blowing agents in comparison to foams prepared in the absence of such phosphorus-containing compounds. Additionally, use of such catalysts provides for a reduced reaction exotherm during the preparation of the foam thereby minimizing foam discoloration or scorching. Preferred phosphorus-containing compounds are the 1-alkyl-1-oxophospholenes, especially 1-methyl-1-oxophospholene.

Abstract: Epoxy resins can be cured or crosslinked with trihydrocarbyl phosphine oxide compounds having epoxy-reactive (active hydrogen) substituents either alone or in combination with amine-terminated polyarylene ethers (e.g., amine-terminated polysulfone oligomers or high polymers.

Abstract: Nonaqueous organic solvent solutions of phosphate esters of epoxy resins. Coating compositions containing these compositions have improved thermal properties as compared to like compositions which are dispersed in water.

Abstract: Thermosetting epoxy resin compositions having improved flame retardancy having combined therewith an effective amount of a dihydroxymethyl phosphine oxide having the general formula ##STR1## wherein R represents an alkyl group having from 1 to about 8 carbon atoms or --R'OH where R' represents an alkylene group having from 2 to about 8 carbon atoms, are disclosed.

Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.

Abstract: Cationic resins based on epoxy resins which are modified through the introduction of phosphoric acid segments and the process of producing the resins are described. The reaction of the phosphoric acid is carried out in a multiple-step process whereby, in a first step, the diester is formed through reaction of ortho-phosphoric acid with 2 moles of a monoepoxy compound or through reaction of a polyphosphoric acid with n-1 moles of a monoalcohol and subsequent reaction with n+1 moles of a monoepoxy compound. The remaining acid group is reacted with a di- or polyepoxy resin. The products obtained can still contain unreacted epoxy groups. The protonable groups are introduced via the epoxy groups and/or via the hydroxy groups present or set free by opening of the oxirane ring. The binders can be combined with hardening components or may be formulated as self-crosslinking binders. The binders have excellent resistance to corrosion when stoved as electrodeposited coatings.

Abstract: Epoxy resins can be cured or crosslinked with triphenyl phosphine oxide compounds having epoxy-reactive (active hydrogen) substituents either alone or in combination with amine-terminated polyarylene ethers (e.g., amine-terminated polysulfone oligomers or high polymers.

Abstract: A method of producing organo-phophorus polymers is disclosed. The polymers will exhibit zero shrinkage and even expansion, will be useful in high voltage, high temperature electrical applications and will exhibit mechanical strength and flame retardant properties.

Abstract: Epoxy resins can be cured by the use of a curing agent formed by the reaction of phosphorus pentoxide with a trialkyl phosphate or phosphonate.

Abstract: The present invention relates to hardenable mixtures containing:(i) a polyglycidyl ether or ester based on an aliphatic, cycloaliphatic or aromatic alcohol or a corresponding carboxylic acid and(ii) a hardener obtainable by reaction of:(A) a mixture of 2-4 mol of a monohydric, aliphatic alcohol and 1 mol of phosphorus pentoxide in an inert organic solvent, or of 2 mol of a dialkyl phosphate or of 2 mol of phosphoric acid, if appropriate in combination with 1-2 mol of a monohydric, aliphatic alcohol, with(B) 0.5-1.5 mol of a diglycidyl ether based on a cycloaliphatic or aromatic diol,with the proviso that the said diglycidyl ether used for the preparation of the hardener has an average molecular weight (number-average) of not more than 2,500 and the said hardener is essentially free from 1,2-epoxide groups.The hardenably mixtures are suitable in particular for the production of coatings.

Abstract: Fluorinated polymers having epoxy resin structure, containing at least 10% by weight, preferably 20% by weight, of fluorine, prepared starting from epichlorohydrin and from one or more diols, at least one of which is a perfluoroalkylene diol, and by using conventional cross-linking agents for epoxy resins, such as anhydrides of dicarboxylic acids, di- or tri-isocyanates, polyfunctional amines.

Abstract: An anodic electrodeposition composition containing a water-soluble or water-dispersible modified epoxy resin derived from an epoxy resin having two epoxide groups and at least one alcoholic hydroxy group at the terminals and the middle of the resin backbone, respectively. The modified epoxy resin has at least one polymeric side chain block bound to said alcoholic hydroxy group and at least one acid group derived from said terminal epoxide group.

Abstract: The paint composition for under coating of the present invention comprises 60 to 90% by weight of an epoxy polyol resin optionally together with a hardener therefor and 10 to 40% by weight of silica particles. Said epoxy polyol resin is obtained by reacting an optionally substituted glycidyl-etherified product of an alkylene oxide adduct of a dihydric phenol with a phosphorus acid having at least one P--OH bond, an ester or a salt thereof to thereby give a precondensate, reacting said precondensate with a dihydric phenol to give an epoxy resin of a high molecular weight, and further reacting said epoxy resin with a compound having an amino group capable of reacting with an epoxy group. Said silica particles comprise a primary particle having an average particle size of 1 to 10 m.mu., a surface area of 270 m.sup.2 /g or above and a concentration of silanol groups on the particle surface of 0.25 mM/100 m.sup.2 or above.

Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.

Abstract: Modified advanced epoxy resins are prepared by reacting (A) an advanced epoxy resin prepared by reacting (1) an epoxy resin having at least one aromatic ring, an average of more than one, but not more than about 2 vicinal epoxy groups per molecule and which contains at least one oxyalkylene or substituted oxyalkylene group per molecule; with (2) a dihydric phenol; with (B) a phosphorus-containing compound.

Abstract: A non-water dispersible, oxirane-defunctionalized, etherified, phosphoric acid ester of an epoxy resin is useful in enhancing the adhesion of aqueous thermosetting coating compositions useful as a varnish or white coating for drawn and ironed aluminum containers. The epoxy resin ester is prepared by reacting(a) an epoxy resin having an epoxy equivalent weight of at least about 190;(b) orthophosphoric acid in an amount of 0.2 to 0.45 equivalents per equivalent of epoxy resin;(c) at least about 0.65 equivalents, per equivalent of epoxy resin, of a reactive hydroxyl-functional compound having at least one hydroxyl group reactive with an oxirane group of said epoxy resin, said hydroxyl-functional compound being a solvent for said epoxy resin and for the non water-dispersible, defunctionalized, etherified, phsophoric acid epoxy resin ester reaction product; and(d) water in an amount of 0-20% of the weight of the orthophosphoric acid.

Abstract: The invention relates to powdered lacquers based on a mixture of epoxide compounds and optionally polyesters as well as salts of primary C.sub.4-18 aliphatic and cycloaliphatic-diamines with phosphoric acid and/or sulphuric acid as a hardener, as well as other additives and a method for the manufacture of flat finish coatings.

Abstract: Composition comprising an epoxy resin, an adduct of a tetra-substituted titanate and a di-substituted hydrogen phosphite, a neutral ester of a phosphorous acid, and a curing agent for the epoxy resin.The composition is particularly useful as an adhesive for bonding structures made of sheet molding compound to like structures, to steel, and to other substrates commonly used in the automotive area.

Abstract: The invention relates to a water-dilutable binder for cationic electrocoating finishes. For the preparation of the binders(A) a di-epoxide compound with an epoxide equivalent weight below 2,000 is reacted with(B) a phenol- or thiol-containing compound which reacts monofunctionally with epoxide groups, and with(C) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or phosphine/acid mixture or a mixture of these compounds, as well as, if desired, with(D) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.The components A and B are used in a molar ratio of from 10:1 to 1:1, preferably from 4:1 to 1.5:1 and the reaction of the component A with the component B is carried out at 100.degree. to 190.degree. C., if desired in the presence of a catalyst.

Abstract: A process for the preparation of a thermoset polymer having good adhesive properties comprising reacting a compound containing a plurality of oxazoline groups with an alkenyl phosphonic acid at a temperature of from about room temperature to about 300.degree. C. is described.

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: A coating composition comprising the reaction product obtained by reacting an epoxy resin with a polynuclear polyhydroxy phenol having adjacent hydroxy groups, polyol esters of polyhydroxy phenolic carboxylic acids having adjacent hydroxy groups or a phosphorus compound.

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: Aminophenoxycyclotriphosphazenes such as hexakis(4-aminophenoxy)cyclotriphosphazene and tris(4-aminophenoxy)-tris phenoxyclyclotriphosphazene are used as curing agents for epoxy resins. These 1,2-epoxy resins are selected from di- or polyepoxide-containing organic moieties of the formula (CH.sub.2 --CHO--CH.sub.2).sub.m --W--R--W--(CH.sub.2 CH--CH.sub.2 O).sub.m where R is diphenyldimethylmethane, diphenylmethane, bis(dibromophenyl)dimethylmethane, or ##STR1## W is a nitrogen or oxygen atom; and m is 1 when W is oxygen and 2 when W is nitrogen. The resins are cured thermally in stages at between about 110.degree. to 135.degree. C. for between about 1 and 10 min, then at between about 175.degree. to 185.degree. C. for between about 0.5 to 10 hr and post-cured at between about 215.degree. and 235.degree. C. for between abut 0.1 and 2 hr. These resins are useful for making fire-resistant elevated temperature stable composites, laminates (e.g.

Abstract: Disclosed are thermosettable compositions comprising (A) an epoxy resin such as the diglycidyl ether of bisphenol A; (B) boron trifluoride complexed with a primary, secondary or tertiary amine such as monoethanolamine and (C) at least one cyclic or acyclic phosphazene having at least one pendant ##STR1## group wherein Z is an alkyl or an aryl group such as hexa(n-propylamino)cyclotriphosphazene.When cured, these compositions have an increased glass transition temperature (Tg) value as compared to a similar composition without the phosphazene compound.These compositions are useful in potting compositions, wet lay-up and pre-impregnated laminate, adhesive, molding, coating, casting, encapsulation, filament winding and transfer molding applications.

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: This invention is directed to organophosphorus compounds useful as epoxy curing agents and adhesion promoters.

Abstract: A process of producing a water dispersible epoxy phosphate-solvent mixture is disclosed which comprises heating the solvent with orthophosphoric acid to reaction temperature together with additional water so that the total amount of water is sufficient to hydrolyze at least about 50% of the oxirane functionality in the polyepoxide which is used, slowly adding a resinous polyepoxide to this heated mixture so that reaction with phosphoric acid and hydrolysis of the oxirane groups will occur simultaneously to minimize the concentration of oxirane functionality in the reaction mixture as the reaction proceeds, thus minimizing epoxy-epoxy reactions which tend to increase the molecular weight of the epoxy phosphate which is formed, and then adding volatile amine to destroy any remaining oxirane functionality and to neutralize the epoxy phosphate to provide a water dispersible epoxy phosphate-solvent mixture.

Abstract: Compounds having the general formula 1 ##STR1## wherein X and Y are functional groups, preferably amino groups, are polymerized with, for example, polyfunctional epoxides to provide heat and fire resistant polymers useful for making flame and fire resistant polymer structures such as for aircraft secondary structures. The groups R in 1 are preferably alkyl and lower halo (e.g., chloro) alkyl.

Abstract: Primary or secondary amino substituted hindered phosphites of the formula ##STR1## are prepared by reaction of the appropriate phosphorus and phenol compounds, said hindered phosphites being useful as stabilizers of organic polymers and lubricating oils.

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

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: Aqueous coating composition, useful on metal substrates which are deep drawn after being coated, e.g., bottle caps, are made from (A) a blend of an aqueous solution of the reaction product of a glycidyl polyether of a dihydric phenol, a polyethylene glycol and phosphoric acid, (B) an aqueous dispersion of a glycidyl polyether of a dihydric phenol and, optionally, (C) an alkoxymethylmelamine.