Abstract: Anaerobically-curing compositions are described comprising (A) a polymerizable monomer; (B) a halogen-containing compound as a first initiator component; (C) an amine, organic sulfimide or perfluoroalkyl sulfonanilide as a second initiator component; and (D) an inhibitor of free-radical polymerization. These compositions are particularly suitable as adhesives and may be formulated as thread-locking adhesives or may be modified by the addition of various modifying polymers to obtain desired properties such as increased viscosities or pressure-sensitive properties.

Abstract: An epoxy resin composition comprising (a) an epoxy resin, (b) a lactone obtained by decarboxylation condensation reaction of a saturated alicyclic 1,2-dicarboxylic acid anhydride, and if necessary (c) a curing agent for the epoxy resin and (d) a curing accelerator gives a cured article showing almost no or very slight curing shrinkage.

Abstract: A self-curing epoxy resin composition is, herein, disclosed produced by irradiating with an electron beam a mixture of 85 to 97 wt % of an epoxy resin and 3 to 15 wt % of a quaternary alkyl ammonium salt of .alpha.,.beta.-unsaturated carboxylic acid or a neutralized product of an .alpha.,.beta.-unsaturated carboxylic acid and a tertiary amine.

Abstract: An O-epoxyalklyated tetrakis (hydroxyphenyl) alkane resin or the esterified reaction product of about one equivalent thereof with less than one equivalent of an ethylentically unsaturated organic acid can be combined with an aqueous alkali- and radiation sensitive, negative acting substance which when coated on a substrate forms a radiation sensitive negative working element.

Abstract: Provides new and improved water-reducible coating compositions and methods of making them. Three preferred processes are disclosed. These differ in the manner of incorporating and chemical nature of an extender polymer.Broadly, the process of the invention is one for forming an aqueous dispersion of a fluent resinous composition ofa. a mixture in an organic solvent of(i) an ionizable graft polymer of an epoxy resin and an addition polymerized resin, the addition polymerized resin being bonded to aliphatic backbone carbon atoms of the epoxy resin by carbon-to-carbon bonds, and(ii) an extender resin;b. an aqueous vehicle, andc. an ionizing agent;the ionization present from said combined components being sufficient to establish the components as a dispersion in the aqueous vehicle, and then addition polymerizing a quantity of addition polymerizable monomer, under addition polymerizing conditions, in said aqueous dispersion, the aqueous dispersion serving as a vehicle therefor.

Abstract: The compositions disclosed herein comprise a mixture of:(1) An unsaturated polyester resin; such as the polymeric ester of maleic acid or anhydride and a glycol such as ethylene glycol; and(2) The reaction product of a polyepoxy compound, such as the diglycidyl ether of bisphenol-A, and an unsaturated monocarboxylic acid, such as acrylic or methacrylic acid, in which reaction product there remains unreacted at the time of mixing with said polyester resin at least 5 percent of the original epoxy groups of said polyepoxy compound.This mixture when molded or cured gives improvement with respect to thermal and humid aging as compared to similar compositions in which the epoxy groups of said reaction product are substantially all reacted prior to mixture with said unsaturated polyester resin. The flexural strength, in particular, of the compositions are better retained on aging without adverse effect on other properties.

Abstract: The product and process is directed to polymerizing second stage ethylenically unsaturated monomers within an aqueous dispersion of a preformed epoxy based resinous material comprising a mixture of graft epoxy polymer containing grafted addition polymer grafted to the epoxy backbone, ungrafted epoxy polymer, and ungrafted addition polymer uniformly dispersed in water wherein the second stage monomers are polymerized in the presence of at least 0.1% of benzoin derivative reducing agent based on monomer weight in combination with a peroxide polymerization initiator.

Abstract: Radiation curable monomers useful in coating compositions are prepared by reacting part of the epoxy groups of a polyepoxide resin with acrylic or methacrylic acid followed by esterifying the remaining epoxy groups with phosphoric acid.

Abstract: Sulfonium-stabilized, water-compatible, radiation-curable vinyl ester resins are prepared by the process of reacting an epoxy resin having on the average at least one vicinal epoxy group with a mercaptan and with an unsaturated monocarboxylic acid to form vinyl ester resins containing sulfide moieties which are then reacted with a protonic acid and an alkylene oxide.Compounds so prepared can be diluted with water and used as coatings.

Abstract: A polymerizable mixture for adhesive bonding is disclosed. The polymerizable mixture comprises a polymerizable acrylic-based material, a polymerizable epoxide-based material and a bifunctional molecular material reactable with said acrylic-based material and said epoxide-based material.

Abstract: Described herein are curable liquid homogeneous mixtures used for the rapid production of fiber-reinforced thermoset resin articles which comprise:(a) a vinyl ester of the following formula: ##STR1## wherein the R's are independently hydrogen or methyl, R.sub.1 is the residue of a cycloaliphatic or aromatic diol and n has an average value of from 1 to about 5.(b) a second crosslinkable oligomer containing two or more unsaturated groups selected from acrylates, methacrylates and fumarate diesters; and(c) a monoethylenically unsaturated monomer, wherein the ratio of (a) to (b) is greater than about 0.3.

Abstract: This invention is directed to thermosettable ethylenically unsaturated epoxy ester resin compositions having improved storage stability and to a method for improving the storage stability of such compositions by adding an anaerobically effective polymerization inhibitor to the resin composition. The resin composition comprises the reaction product of a bisphenol-base epoxy resin, a novolac-base epoxy resin, or a mixture thereof with an ethylenically unsaturated monocarboxylic acid dissolved in a polymerizable monomer containing a >C.dbd.CH.sub.2 group. The polymerization inhibitors of this invention are 4-chloro-2-nitrophenol, 2,4-dichloro-6-nitrophenol, or mixtures thereof.

Abstract: There is provided a coating composition (B) consisting essentially of:a composition (A) anda photopolymerization initiating effective amount of a photoinitiator,said composition (A) containing:(i) 80 to 90% by weight of at least one polyfunctional monomer having three or more (meth)acryloyloxy radicals per molecule,(ii) 5 to 10% by weight of at least one acrylic monomer having two or less functional groups and(iii) 5 to 10% by weight of a phenol novolak epoxy (meth)acrylate oligomer of the formula: ##STR1## where, X.dbd.H, CH.sub.3,X.dbd.H, CH.sub.3, Br andn=0-8with the proportion of oligomer wherein n of 4.ltoreq.n.ltoreq.8 is more than 20 wt % with respect to the total amount of the novolak epoxy (meth)acrylate.

Abstract: Epoxy ester copolymer dispersible in water with the aid of an amine, which may be ammonia, is provided by esterifying a polyepoxide having a 1,2-epoxy equivalency in excess of 1.0 and a molecular weight of from 350 to 8000 with at least 0.5% of the weight of the copolymer of a monoester of a saturated monohydric alcohol with a monoethylenically unsaturated dicarboxylic acid which resists homopolymerization. This polyepoxide ester is copolymerized with from 15% to 70% of monoethylenic monomers, based on the weight of the copolymer, these monoethylenic monomers including carboxyl functional monomer providing an acid number of from 20-150 in the copolymer.

Abstract: Provides new and improved water-reducible coating compositions and methods of making them. Three preferred processes are disclosed. These differ in the manner of incorporating and chemical nature of an extender polymer.Broadly, the process of the invention is one for forming an aqueous dispersion of a fluent resinous composition ofa. a mixture in an organic solvent of(i) an ionizable graft polymer of an epoxy resin and an addition polymerized resin, the addition polymerized resin being bonded to aliphatic backbone carbon atoms of the epoxy resin by carbon-to-carbon bonds, and(ii) an extender resin;b. an aqueous vehicle, andc. an ionizing agent;the ionization present from said combined components being sufficient to establish the components as a dispersion in the aqueous vehicle, and then addition polymerizing a quantity of addition polymerizable monomer, under addition polymerizing conditions, in said aqueous dispersion, the aqueous dispersion serving as a vehicle therefor.

Abstract: A process for preparing thermoset polymer spheres by polymerizing a thermosettable polymer such as a vinyl ester resin or an unsaturated polyester resin in water containing a suspending agent in the presence of a catalyst and an accelerator is improved by employing an organic suspending agent as the suspending agent.

Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.

Abstract: A resin composition for aqueous paint is produced by exposing to electron beams a mixture comprising 50 to 95 wt % of an epoxy resin, 1 to 23 wt % of an ethylenically unsaturated monomer having a carboxyl group and 4 to 44 wt % of a monomer having one ethylenically unsaturated bond in the molecule. The resin composition provides a coating having good coating surface, adhesion strength, solvent resistance, water resistance and processability.

Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there is a double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.

Abstract: Water-borne thermoplastic polyhydroxyether resins are prepared by grafting carboxyl-containing vinyl monomers onto phenoxy resins with a free radical initiator and then converting the graft copolymer to an ionomer suitable for use as protective coatings for metals.

Abstract: This invention relates to a heat curable composition comprising(a) a liquid, ethylenically unsaturated monomer, oligomer or prepolymer of the formula: ##STR1## wherein R is H or CH.sub.3, R.sub.1 is an organic moiety and n is at least 2,(b) an epoxy resin containing at least two ##STR2## groups, and (c) a thermal initiator member of the group consisting of(1) a substituted or unsubstituted diaryliodonium salt in combination with a free radical initiator,(2) a BF.sub.3 adduct,(3) a BF.sub.3 adduct in combination with a free radical initiator, and(4) dicyandiamide in combination with a free radical initiator.The system is stable at ordinary temperatures, but on heating the thermal initiator catalyzes the curing of the acrylate and the epoxy resin.

Abstract: A process for preparing a cathodic electrodepositable coating composition which comprises, in sequence,(i) epoxidizing a high-molecular-weight compound containing a carbon-carbon double bond and having a molecular weight of 500 to 10,000 and an iodine value of 100 to 500 to form an epoxidized high-molecular-weight compound containing 0.5 to 12% by weight of oxirane oxygen,(ii) reacting a part of the epoxy groups of the epoxidized high-molecular-weight compound with a basic amine compound of the general formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrocarbon group having 1 to 10 carbon atoms which may be partly replaced by a hydroxyl group, and R.sub.1 and R.sub.2 together may form a cyclic structure,(iii) reacting a part or the whole of the remaining epoxy groups with an .alpha.,.beta.-unsaturated monocarboxylic acid of the general formula ##STR2## wherein R.sub.3 and R.sub.

Abstract: A photosetting composition comprises an unsaturated acid-modified bisphenol type epoxy compound having an acryloyl radical; an oligoester diacrylate compound having a molecular weight of 420 or more; a photopolymerizable acrylate type monomeric compound having a molecular weight of 100 to 400; a bisphenol type epoxy resin having a softening point of 50.degree. C. to 150.degree. C. or a saturated acid-modified bisphenol type epoxy resin having a softening point of 50.degree. C. to 150.degree. C.; and a photopolymerization initiator, said composition having a proper viscosity and an excellent photocuring reaction rate and being able to form a photocured resinous film or article having a satisfactory Dupont impact strength, impact bending strength, and bonding property to metallic materials.

Abstract: A family of polyfunctional surface-active comonomers which act to improve the adhesion between a resin or composite material and solid surfaces capable of binding polyvalent cations is described. These polyfunctional surface-active comonomers, or "PolySACs", are preferably the reaction product of an epoxy acrylate or methacrylate and an aminobenzoate. The adhesion of the resin or composite material to certain solid surfaces is also improved by the preparatory treatment of these surfaces with a monobasic acid of intermediate strength followed by treatment with a mordant.In its most preferred form the invention is employed in reconstructive dental work to improve the adhesion between a resin or composite material and dentin. The dentin is cleansed with isotonic formic acid, treated with an isotonic ferric chloride mordant and then treated with a PolySAC which is the reaction product of an oligomeric diglycidyl ether, acrylic acid and lithium ortho-aminobenzoate. The resin or composite material is then applied.

Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## Where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ--C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make cross-linkable blends with unsaturated resins or monomers and to make laminates.

Abstract: Water-borne thermoplastic polyhydroxyether resins are prepared by grafting carboxyl-containing vinyl monomers onto phenoxy resins with a free radical initiator and then converting the graft copolymer to an ionomer suitable for use as coatings or adhesives.

Abstract: Curable compositions which cure into bubble-free articles include as a resinous component, a vinyl ester resin, a ketone peroxide as a catalyst and as a promoter (a) a complex of equivalent amounts of a cobalt salt and an aldimine chelating agent which is the reaction product of equivalent amounts of salicylaldehyde and a polyamine or (b) cobalt naphthenate and about an equivalent amount of aldimine chelating agent which is the reaction product of salicylaldehyde and a polyamine or (c) a combination of (a) and (b).

Abstract: Curable vinyl ester resin compositions, that can be B-staged with magnesium oxide, comprise a vinyl ester resin having no free carboxyl groups, a reactive diluent, and a thickening agent which is the reaction product of a polyethylene glycol having a molecular weight greater than 2,000 and an anhydride of a polycarboxylic acid with the thickening agent having more than two carboxyl groups per molecule.

Abstract: An improved adhesive composition formed by combining two parts. One part includes one or more polymerizable materials comprising one or more acrylate or methacrylate groups per molecule and a source of free radicals comprising an organic peroxide, hydroperoxide, perester or peracid. The other part includes an activator which is a specifically defined organic material which can cooperate with the source of free radicals to initiate addition polymerization of the polymerizable materials.

Abstract: Non-gelled compositions containing hydroxy ester copolymer having carboxyl groups and substantially free of oxirane groups are disclosed which are the esterification reaction product of(a) acidic addition copolymer; and(b) a polyepoxide which has been partially defunctionalized by reaction with carboxyl containing polybutadiene polymer. The resulting composition is neutralized with amine, is self-emulsifiable in water and is useful for coatings.

Abstract: Novel sulfonium-stabilized, radiation-curable, water-compatible, water-in-oil emulsions and a method of preparation are described. As an example, one such emulsion was prepared by reacting the diglycidyl ether of a polypropylene glycol with essentially a stoichiometric equivalent of acrylic acid, about 0.3 equivalent of bis(2-hydroxyethyl)-sulfide and 1.5 equivalents of H.sub.2 O.

Abstract: The stability to phase separate solutions of unsaturated polyesters, vinyl ester resins or mixtures thereof and an elastomeric additive is improved by the use of a compatibilizing agent which is the ester of a carboxyl terminated diene polymer and a polyoxyalkylene.

Abstract: Nitric acid, alone or in combination with phenothiazine, increases the storage life of vinyl ester resins or unsaturated polyesters without adversely suppressing the exotherm or affecting their curability.

Abstract: Binders water-dilutable upon neutralization with inorganic and/or organic acids comprising the reaction product of (A) resins having at least 2 1,2-epoxy groups per molecule and an epoxy equivalent of at least 160; and (B) a semiester of a dicarboxylic acid and an N-2-hydroxyalkyloxazolidine, and a process for the formation of the binders, is described. The binders have sufficient basic groups for neutralization with acids to provide water dilutability, as well as the functional groups required for crosslinking of the binders. The binders upon stoving provide films with good resistance characteristics and have reduced losses.

Abstract: Cycloalphatic acrylate compositions and methods of making them are disclosed. The compositions are mixtures containing dicyclopentadiene (meth) acrylate and (meth) acrylates such as the mono and di (meth) acrylates of tri, and tetracyclopentadiene and a mixture of the copolymers of (meth) acrylic acid with adducts of cyclopentadiene with isoprene and/or piperylene and a mixture of poly (meth) acrylates having the repeating unit ##STR1## where R.sup.1 is hydrogen or ##STR2## R.sup.2 is CH.sub.2 .dbd.CZ-C(O)--O-- Z is H, or methyln is 0, 1 or 2 andm is 0 or 1 and when m is 0 there isa double bond present.The compositions are useful to make crosslinkable blends with unsaturated resins or monomers and to make laminates.

Abstract: The invention comprises a polymerizable liquid mixture of (a) a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of about 1.5 to less than about 4, m is equal to the free valence of R less the average value of n, R is the hydroxyl-free residue of an organic polyol which contained from 2 to 4, inclusive, hydroxyl groups, OH, in formula (I) (b) maleic anhydride, (c) an epoxide containing two or more 1,2-epoxide radicals, (d) an ethylenically unsaturated monomer which forms a liquid homogeneous mixture with the half ester, maleic anhydride and epoxide, and (e) a basic compound.

Abstract: A vinyl ester resin composition having excellent physical, mechanical and handling properties is provided which comprises: a vinyl ester resin made by condensing an epoxy resin and an ethylenically unsaturated monocarboxylic acid; and a thixotropy imparting amount of a thixotropy imparting material selected from at least one condensation product of a sugar alcohol with an aromatic aldehyde.

Abstract: Monoesters of fumaric acid and dicyclopentadienyl alcohol halogenated with one or two atoms of a halogen are compounds useful as reactive diluents for polyesters or vinyl ester resins.

Abstract: A strand prepreg which comprises (i) a resin composition comprising 100 parts by weight of thermosetting resin having a softening point of 60.degree. C. or less and about 5 to 60 parts by weight of epoxy resin having a number average molecular weight of 5,000 or more and (ii) about 20 to 80% by volume strands of carbon fibers, glass fibers, aromatic polyamide fibers and the like, wherein the strands are impregnated with the resin composition.

Abstract: Water-borne reaction products of (a) carboxylfunctional polymers; (b) modified polyepoxides; and (c) tertiary amines are useful as film-forming components of coating compositions which can be spray-, flow-, dip-, roller-, or electro-coated. The coating compositions are useful as such or can be crosslinked with crosslinking agents such as a nitrogen resin and, when coated on metal and paper substrates, they provide coatings of improved properties, including a high degree of flexibility during machining and stamping of the coated articles, corrosion resistance, gloss, hydrolytic stability, and nonadulterating of foods and beverages in contact therewith.

Abstract: The present invention provides an improved process for reducing the premature gelation during esterification of epoxy compounds containing tertiary, allylic or benzylic hydrogens (e.g., saturated epoxy resins) with ethylenically unsaturated monocarboxylic acids (e.g., acrylic acid) wherein the epoxy compound in pre-reacted with a trialkylphosphite (e.g., triethylphosphite) prior to the esterification.

Abstract: The present invention provides an improved process for reducing the premature gelation during esterification of epoxy compounds containing tertiary, allylic or benzylic hydrogens, e.g., saturated epoxy resins, with ethylenically unsaturated monocarboxylic acids, e.g., acylic acid, which comprises prereacting the said epoxy compound with a hydroxylamine compound prior to the esterification step.

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

Abstract: A cis-trans fluoropolyol acrylate prepared by reacting acrylic acid anhyde with a fluoropolyol having the structural formula: ##STR1## where R is selected from the group consisting of --C(CF.sub.3).sub.2 C.sub.6 H.sub.4 C(CF.sub.3).sub.2 -- and --C(CF.sub.3).sub.2 CH.sub.2 CH.dbd.CH(CF.sub.3).sub.2 C--, R' is selected from the group consisting of --H and --CF.sub.2).sub.x F, x is 1 to 8 and n is any integer from 1 to 15, and the crosslinked thermosetting polymer prepared therefrom. The fluoropolyacrylate is useful in fabricating castings, coatings or adhesives.

Abstract: A resin composition is disclosed. The composition comprises an organic resin, a halogenated flame retardant incorporated within the organic resin, and a synergistic smoke suppressive filler of calcium carbonate and alumina trihydrate.

Abstract: The invention is concerned with novel autoxidizable compositions comprising an unsaturated acid ester of a glycol monodicyclopentenyl ether, a condensation or vinyl addition polymer, a siccative and a volatile stabilizer, which compositions are uniquely adapted to be formulated with high solids and practical viscosity ranges for coating and/or impregnating purposes.

Abstract: The method of fabrication of a laminate formed by at least two transparent sheets consists in forming a stack of sheets after coating the sheet interfaces with a polymerizable adhesive, in subjecting the stack to an overpressure below or equal to 2 bar, in maintaining at the same time a temperature T below the maximum temperature of stability of the adhesive for a sufficient period of time to obtain prepolymerization of the adhesive, then in maintaining the stack temperature below or equal to the temperature T for a period of less than sixteen hours.

Abstract: Air-drying unsaturated coating compositions are obtained by reacting at least 60% of the epoxide groups of a polyepoxid with more than one epoxid group per molecule(a) with 0.01 to 0.5 NH-equivalents, based on one epoxide group of ammonia, an aliphatic or cycloaliphatic primary or secondary amine and subsequently(b) with 0.99 to 0.5 carboxyl equivalents, based on one epoxide group of acrylic or methacrylic acid.The reaction products may be mixed with solvents and/or copolymerizable monomers and are preferably hardened in the presence of known photoinitiators with the aid of energy radiation.Their particular advantages are their stability in the dark and that they also harden very quickly in the presence of atmospheric oxygen.Preferred substrates are paper and cardboards.

Abstract: Thermosetting resin compositions containing vinyl ester resins having terminal unsaturation, vinyl aromatic monomers, and dicyclopentadiene alkenoate concentrates are useful to make fibrous reinforcement laminates. The use of the dicyclopentadiene alkenoate concentrate accelerates the rate at which hardness develops during room temperature cure.

Abstract: Vinyl ester resins with improved impact resistance and other benefits and advantages may be obtained by a process modification wherein up to 20 percent of the unsaturated monocarboxylic acid, which is reacted with a polyepoxide, is replaced by an equivalent amount of a liquid carboxy terminated polydiene rubber capable of reacting with epoxy groups to form a chemically bound molecule. .Iadd.