An emulsified reactive epoxy polymer composition which is readily dispersed in water and is particularly suited for use in a coating composition which may be cured at ambient temperatures. The emulsifiable epoxy composition incorporates a hydrophilic polyoxyalkylene segment.

The invention relates to reactive epoxy polymer compositions emulsified in
 water comprising a polymeric epoxy emulsion and an emulsified reactive
 polymer curing composition. In another aspect, the invention relates to a
 process for preparing such water emulsified reactive polymer compositions.
 In yet another aspect, the invention relates to cured coatings resulting
 from further reaction of the water emulsified reactive polymer
 compositions on a suitable substrate.
 Two-part epoxy resin based coating systems generally comprise a curable
 epoxy resin and a curing agent for the epoxy resin, and are commonly
 dispersed or dissolved in a solvent, primarily an organic solvent, to
 prepare coating compositions, for example paints and floor sealants. The
 use of such organic solvent-based coating compositions is discouraged on
 environmental grounds. On the other hand, such cured epoxy resin based
 coatings provide hard and abrasion resistant coatings which are resistant
 to, among others, hydrocarbons and aqueous media.
 Water-based resin systems consisting of an epoxy resin and a curing agent
 dissolved or emulsified in water have been developed, and create less
 environmental and health concerns. The development of such systems is
 reviewed by Chou (Polymers Paint Colour Journal, Vol. 184,1994, pp
 413-417). Water-based resin systems are described in U.S. Pat. No.
 4,289,826, in GB-A-1,533,825, and in GB-A-1,380,108. Known two part
 water-based epoxy resin emulsion coating compositions have significant
 disadvantages as described by Chou. In particular, the deficiencies of
 amidoamine adducts or modified polyamines which disperse liquid epoxy
 resin at the point of application is clearly described: these curing
 agents are normally made water dispersible by salt formation with volatile
 organic acids. These acids often create odor, flash rusting and water
 sensitivity problems. The problems of flash rusting and corrosion are
 dealt with in detail by M. A. Jackson, "Guidelines to Formulation of
 Waterborne Epoxy Primers", Polymers Paint Colour Journal, October 1990,
 Vol. 180, No 4270, pp 608-621 and by H. Leidheiser, Jr., "Mechanism of
 Corrosion Inhibition with Special Attention to Inhibitors in Organic
 Coatings", Journal of Coatings Technology, October 1988, pp 97-106.
 In general, it is difficult to develop stable emulsions which have high
 solids content and low viscosity, and therefore good flowability.
 Furthermore, many of the known systems display poor coating properties, as
 they do not readily coalesce without solvents when coated on a substrate,
 resulting in cured coatings with poor mechanical flexibility and adhesion,
 high porosity and excessively high film formation temperature for ambient
 cure applications. Such systems have a limited balance between hydrophobic
 and hydrophilic properties, resulting in limited flexibility in the
 formulation of coatings. Such systems may also suffer from the inability
 to effectively incorporate pigments into the coating composition.
 Therefore, pigments are often blended with the curing agent by means of
 grinding or agitation.
 U.S. Pat. No. 5,118,729 describes improved aqueous epoxy dispersions
 obtained by grafting an emulsifier containing polyoxyethylene residues by
 reaction on to a terminal epoxy reactive group of the epoxy molecule prior
 to dispersion.
 U.S. Pat. No. 5,344,856 describes an emulsifiable epoxy resin composition
 which forms a water stable emulsion comprising the reaction product of a
 polyepoxide type compound with nominally difunctional C.sub.12-36 fatty
 acids, dispersed by means of the addition of a surfactant wherein the
 surfactant comprises an alkyl aryloxy poly (propyleneoxy) poly
 (ethyleneoxy) ethanol or a C.sub.12-36 hydrocarbyloxy poly (propyleneoxy)
 poly (ethyleneoxy) ethanol wherein the hydrocarbyloxy moiety is the
 residue of a C.sub.12-36 fatty alcohol or C.sub.12-36 fatty acid: standard
 chain terminating agents may be employed.
 U.S. Pat. No. 3,297,519 describes epoxy resins which are self-dispersible
 in water without further dispersing aids in a concentration up to 10
 percent by weight: the resins described are selected glycidyl ethers based
 on bisphenol-A containing tailored blocks of polyoxyethylene bridging the
 two bisphenol-A residues in the molecule. These products are used as
 components of paper finishes.
 U.S. Pat. No. 5,319,004 describes water dispersible hardeners for epoxy
 resins produced from the reaction of specific polyamidoamides with
 specific polyamines and specific adducts of polyepoxy compounds with
 polyalkylene polyether polyols.
 WO-A-9501387 describes the preparation of self-dispersible curable epoxy
 compositions prepared by the reaction of an epoxy resin with a polyhydric
 phenol and an amine-epoxy adduct: the amine-epoxy adduct is a reaction
 product of an aliphatic polyepoxide and a polyoxyalkyleneamine. The
 products described are asserted to require a catalyst to promote the
 amine-epoxy adduct reaction with the polyhydric phenol and epoxy resin,
 and the dispersion of the self dispersible, curable epoxy resin is stated
 to require high shear in specially designed equipment. Specific reaction
 sequencing is stated to be necessary in order to avoid post-addition of
 the amine-epoxy adduct to the epoxy resin, with such addition leading to
 unstable aqueous dispersions.
 DE-A-4405148 describes water dispersible epoxy compositions derived from
 the reaction of aromatic epoxy resins, bisphenol-A and polyglycidyl ether
 polyepoxides, which resins may be cured with conventional amine curing
 agents for aqueous systems. Dispersion of the water-dispersible epoxy
 compositions are stated to require high shear.
 JP-A-H6-179801 describes water-based curable epoxy resin compositions
 prepared from an epoxy resin, a self-emulsifiable active organic amine
 curing agent and water. Ease of dispersion is obtained by choice of the
 curing agent. The application of the technology described two epoxy resins
 with an epoxy equivalent weight of less than 200 is asserted: good
 leveling and film forming properties are asserted.
 EP-A-EP 0617726 describes a water miscible or soluble amine-terminated
 resin useful as a curing agent for water-dispersible epoxy resins which
 amine-terminated resin is the reaction product of: 1) a polyamine
 component comprising one or more hydrophilic amine-terminated polyalkylene
 glycols, and, optionally, one or more hydrophobic polyamines; 2) a
 polyepoxide derived from a polyalkylene glycol or cycloalkylene glycol,
 and optionally hydrophobic polyglycidyl ethers, and, optionally, an amine
 extender having two active amine hydrogen atoms, and reaction products
 therefrom; 3) optionally a reactive diluent; and 4) optionally a catalyst
 for the reaction of an amine with an epoxy resin.
 Despite the improvements made to date, the formation of stable aqueous
 dispersions of emulsified reactive polymer compositions derived from epoxy
 resins with an epoxy equivalent weight greater than 350 and aqueous
 dispersed or dispersible curing agents is generally difficult. Dispersions
 of such compositions containing no solvent, exhibit a viscosity higher
 than optimal. In particular, two-component pre-dispersed compositions are
 desired which cure at low ambient temperature to provide final coatings
 with good mechanical properties.
 It is desirable to provide emulsified reactive epoxy polymer compositions
 which can be produced in presently employed industrial reactors. It is
 also desirable that such reactive epoxy polymer compositions should be
 stable without the addition of acid or a significant quantity of organic
 solvent, in order to optimize final coating properties. It is further
 desirable that such reactive epoxy polymer compositions should also accept
 and disperse the commonly used hydrophobic curing agents, which may be
 required in certain applications to allow economically attractive low
 ambient temperature curing while still providing final coatings with
 excellent mechanical properties.
 The present invention provides a reactive polymer emulsion preparable by:
 (i) reacting at least one polyepoxide (II) with at least one
 polyoxyalkylene glycol diglycidyl ether (III), optionally a polyhydroxy
 hydrocarbon (IX), and optionally an advancement catalyst(XI), to produce a
 first reaction product,
 (ii) reacting the first reaction product with a polyoxyalkylenediamine and
 optionally at least one further amine (V), to produce a second reaction
 product (VIII),
 (iii) emulsifying the second reaction product (VIII) in water to provide an
 aqueous polymeric epoxy emulsion (VII) and
 (iv) dispersing or dissolving a curing agent (XII) in the aqueous polymeric
 epoxy emulsion (VII) of the reaction product (VIII) to provide an
 emulsified reactive polymer composition (I), wherein the organic solvent
 content, if any, of the of the composition (I) is not more than 1.5
 percent.
 The said at least one further amine preferably includes a monofunctional
 amine, a polyamine, or a mixture of two or more thereof.
 The invention also provides a process for preparing a reactive polymer
 emulsion (I) comprising:
 (i) reacting at least one polyepoxide (II) with at least one
 polyoxyalkylene glycol diglycidyl ether (III), optionally a polyhydroxy
 hydrocarbon (IX), and optionally an advancement catalyst (XI), to produce
 a first reaction product,
 (ii) reacting the first reaction product with a polyoxyalkylenediamine and
 optionally at least one further amine (V), to produce a second reaction
 product (VII),
 (iii) emulsifying the second reaction product (VII) in water to provide an
 aqueous polymeric epoxy emulsion (VII) and
 (iv) dispersing or dissolving a curing agent (XII) in the polymeric epoxy
 emulsion (VII) to provide an emulsified-reactive polymer composition (I),
 wherein the organic solvent content, if any, of the composition (I) is not
 more than 1.5 percent.
 In a further aspect, the invention provides a coating composition
 comprising the cured product derived by curing the emulsified reactive
 epoxy polymer composition (I).
 The emulsified reactive polymer composition (I) demonstrates good
 stability, wettability and viscosity characteristics. Furthermore, the
 coatings prepared from the emulsified reactive epoxy polymer composition
 (I) demonstrate good adhesion coalescence, flexibility, resiliency and
 toughness.
 The term "emulsion" is used herein to indicate a stable mixture, wherein in
 the polymeric epoxy emulsion (VII) or the dispersion of curing agent (XII)
 the continuous phase is water and the dispersed phase is the emulsified
 reactive epoxy polymer composition or the curing agent (XII). The term
 "emulsifiable" as used herein describes matter which is capable of forming
 a stable oil in water emulsion. The term "emulsified" as used herein
 indicates matter present in the dispersed phase. The term "stable
 emulsion" as used herein refers to an emulsion in which the dispersed
 components do not settle to the bottom and form a solid cake at ambient
 temperature for a period of six months at 23.degree. C. The term "stable
 emulsion" as used herein does not exclude compositions in which some
 settling of particles with time to form a soft deposit which is easily
 redispersible by agitation occurs. This six months emulsion stability at
 23.degree. C. may be simulated in a test where emulsion stability over a
 four week period at 40.degree. C. is observed.
 The term "reactive polymer" is used herein to indicate a polymeric species
 capable of further chemical reaction by virtue of reactive functional
 groups present within the polymer backbone, pendant to the polymer chain
 or terminal to the polymer chain.
 The term "polyepoxide" as used herein indicates a compound which contains,
 on average, more than one epoxy moiety per molecule. Also included are
 partially advanced epoxy resins, that is, the reaction product of a
 polyepoxide and a polyhydroxy hydrocarbon compound wherein the reaction
 product has an average of more than one unreacted epoxide unit per
 molecule. Polyepoxides (polyglycidyl ethers of a polyhydroxy hydrocarbon)
 may be prepared by reacting an epihalohydrin with a polyhydroxy
 hydrocarbon or a halogenated polyhydroxy hydrocarbon. Such preparation is
 well known in the art. See Kirk-Othmer Encyclopedia of Chemical Technology
 3rd Ed. Vol. 9 pp. 267-289.
 The epihalohydrins correspond to Formula 1 wherein:
 ##STR1##
 Y is a halogen, preferably chloro or bromo, and most preferably chloro;
 and R is hydrogen or C.sub.1-14 alkyl, and more preferably methyl.
 Polyhydroxy hydrocarbon means herein a compound with a hydrocarbon backbone
 and on average more than one primary or secondary hydroxy moiety,
 preferably the average hydroxy moieties per hydrocarbon molecule is two or
 more. Halogenated polyhydroxy hydrocarbon means herein a polyhydroxy
 hydrocarbon which is substituted with one or more halogens. The hydroxyl
 moieties may be bound to aromatic aliphatic or cycloaliphatic moieties.
 Among preferred classes of polyhydroxy hydrocarbons and halogenated
 polyhydroxy hydrocarbons are the bisphenols; halogenated bisphenols;
 hydrogenated bisphenols; and novolac resins, that is, the reaction product
 of phenols and simple aldehydes, preferably formaldehyde. The reaction
 product of phenol and an aldehyde, preferably formaldehyde, is a
 well-known product, as is the process for its production. Such a product
 is commonly referred to as a novolac resin.
 Preferred polyhydroxy compounds (IX) useful in this invention pond to
 Formula 2
 ##STR2##
 wherein:
 A is an aryl moiety; aryl moiety substituted with an alkyl or halo moiety;
 a polyaryl moiety wherein the aryl moieties are connected by direct bonds,
 alkylene, haloalkylene, cycloalkylene, carbonyl, sulfonyl, sulfinyl,
 oxygen, or sulfur, such poly aryl moieties being optionally substituted
 with one or more alkyl or halo moieties; or the oligomeric reaction
 product of an aldehyde and phenol;
 and u is greater than 1. Preferably u is from greater than 1 to 10, even
 more preferably from greater than 1 to 3, and most preferably, from 1.9 to
 2.1.
 More preferred polyhydroxy hydrocarbons and halogenated polyhydroxy
 hydrocarbons include those corresponding to Formulas 3 to 6:
 ##STR3##
 wherein R.sup.1 is separately in each occurrence C.sub.1-10 alkylene,
 C.sub.1-10 haloalkylene, C.sub.4-10 cycloalkylene, carbonyl, sulfonyl,
 sulfinyl, oxygen, sulfur, a direct bond or a moiety corresponding to
 Formula 7
 ##STR4##
 R.sup.2 is separately in each occurrence C.sub.1-3 alkyl or a halogen;
 R.sup.3 is separately in each occurrence C.sub.1-10 alkylene or C.sub.5-50
 cycloalkylene;
 Q is separately in each occurrence a tetravalent C.sub.1-10 hydrocarbyl
 moiety;
 Q is separately in each occurrence hydrogen, cyano, or a C.sub.1-14 alkyl
 group;
 a is in each occurrence 0 or 1;
 m is independently in each occurrence from 0 to 4;
 m' is separately in each occurrence from 0 to 3; s is from 0 to 4; and
 t is from 1 to 5.
 Even more preferable polyhydroxy hydrocarbons are those represented by
 Formulas 3 and 4 and 5.
 R.sup.1 is preferably C.sub.1-3 alkylene, C.sub.1-3 haloalkylene, carbonyl,
 sulfur, or a direct bond; more preferably a direct bond, propylene, or
 fluorinated propylene (--C(CF.sub.3).sub.2 --); and most preferably
 propylene. R.sup.2 is preferably methyl, bromo or chloro; and most
 preferably methyl or bromo. R.sup.3 is preferably C.sub.1-3 alkylene or a
 polycyclic moiety corresponding to Formula 8
 ##STR5##
 wherein:
 t is from 1 to 5 inclusively, preferably from 1 to 3, and most preferably
 1. Preferably, m' is from 0 to 2. Preferably, m is from 0 to 2.
 Preferably, s is from 0 to 8; and more preferably from 0 to 4.
 Among preferred polyhydroxy hydrocarbons are the dihydroxy phenols.
 Preferable dihydroxy phenols include those which contain substituents that
 are non-reactive with the phenolic groups. Illustrative of such phenols
 are 2,2-bis(3,5-dibromo-4-hydroxyphenyl) propane; 2,2-bis(4-hydroxyphenyl)
 propane; 2,2-bis(3,5-dichloro-4-hydroxyphenyl) propane;
 bis(4-hydroxyphenyl) methane; 1,1-bis(4-hydroxyphenyl)-1-phenylethane;
 1,1'-bis(2,6-dibromo-3,5-dimethyl-4 hydroxyphenyl) propane;
 bis(4-hydroxyphenyl) sulfone; bis(4-hydroxyphenyl) sulfide; resorcinol and
 hydroquinone. The preferred dihydroxy phenolic compounds are
 2,2-bis(4-hydroxyphenyl) propane (bisphenol A), 2,2 bis(4-hydroxyphenyl)
 methane (bisphenol F) and 2,2-bis(4-hydroxy-3,5-dibromophenyl) propane.
 Cycloalkylene as used herein refers to monocyclic and polycyclic
 hydrocarbon moieties. As used herein haloalkyl refers to a compound with a
 carbon chain and one or more of the hydrogens replaced with a halogen.
 Haloalkyl also means compounds wherein all of the hydrogen atoms have been
 replaced by halogen atoms. Alkylene as used herein refers to a divalent
 alkyl moiety.
 The polyepoxides useful in the invention preferably correspond to Formula 9
 ##STR6##
 wherein A, u and R are previously defined.
 Preferably the polyepoxides are chosen such that the reaction product
 (VIII) is not significantly crosslinked. Such highly crosslinked reaction
 products form gels and do not form good coatings. Some branching may be
 present as long as the reaction product does not form a gel.
 The polyepoxides more preferably correspond to one of Formulas 10 to 13
 ##STR7##
 wherein R, R.sup.1, R.sup.2, R.sup.3, a, m, m', s and t are as defined
 previously; r is from 0 to 40. Preferably, r is from 0 to 10, and most
 preferably 1 to 5. Preferably, s is from 0 to 8; and most preferably 0 to
 4. The symbols, a, m, m', r, s, and t may represent an average number, as
 the compounds to which they refer are generally found as a mixture of
 compounds with a distribution of the units to which they refer.
 If a polyepoxide corresponding to Formula 12 is used in the preparation of
 reaction product (VIII), then s should be chosen such that the reaction
 product is not crosslinked to a stage that gel formation occurs.
 Preferably, s is from 0 to 3.
 Polyoxyalkylene glycol diglycidyl ether (Ill) as used herein refers to a
 compound or a mixture of compounds which contains, on average, more than
 one epoxy moiety per molecule, and which may be prepared by reacting an
 epihalohydrin corresponding to Formula (1) with one or more polyhydroxy
 compounds or halogenated polyhydroxy compounds corresponding to Formula
 (14)
 ##STR8##
 where R.sup.4 is separately in each occurrence hydrogen, methyl,
 halomethyl, or ethyl, with a proviso that if one R.sup.4 on an alkoxy unit
 is ethyl the other must be hydrogen;
 and q is from 1 to 400. Preferably, q is from 20 to 350, more preferably
 from 40 to 300. The symbol q represents an average number, as the
 compounds to which it refers are generally found as a mixture of compounds
 with a distribution of units to which q refers.
 The polyoxyalkylene glycol diglycidyl ethers (Ill) correspond to Formula 15
 ##STR9##
 wherein R, R.sup.4 and q are as defined previously.
 In reaction product (VII) the polyepoxide (II) used preferably corresponds
 to Formulas 10, 11, or 12, and the polyoxyalkylene glycol diglycidyl ether
 (III) corresponds to the Formula 15. In another preferred embodiment, the
 polyepoxide (II) used in reaction product (VIII) is from 85 to 99.5
 percent by weight of polyepoxides corresponding to Formulas 10, 11, and
 12, and 0 to 15 percent by weight of the polyoxyalkylene glycol diglycidyl
 ether (III) corresponding to Formula 15. In a more preferred embodiment 85
 to 99.5 percent of the polyepoxide used in reaction product (VIII)
 corresponds to Formula 10 and 0.5 to 15 percent of the polyoxyalkylene
 glycol diglycidyl ethers (III) corresponds to Formula 15.
 The amine composition (V) is present in sufficient quantity such that in
 combination with the polyoxyalkylene glycol diglycidyl ether (III) the
 polymeric epoxy reaction product (I) has sufficient hydrophilic-lipophilic
 balance that the polymeric epoxy reaction product (I) is water
 dispersible. Hydrophilic (poly)amines or hydrophobic (poly)amines may be
 present in the amine composition. The polyoxyalkylene diamine (V) is a
 polyalkylene glycol terminated with primary or secondary amine moieties.
 The polyalkylene glycol chains useful herein can comprise units derived
 from C.sub.2-8 oxides, or C.sub.2-8 glycol ethylene oxide, propylene
 oxide, butylene oxide, ethylene glycol, propylene glycol, butylene glycol,
 a butane diol (such as 1,4-butane diol), tetrahydrofuran, a propane diol
 (such as 1,2- or 1,3-propane diol) or a mixture thereof. Preferably the
 polyoxyalkylene glycol chain is comprised of units derived from ethylene
 oxide, propylene oxide, a mixture of ethylene oxide and propylene oxide,
 or tetrahydrofuran and more preferably of units derived from ethylene
 oxide or a mixture of units derived from ethylene oxide and propylene
 oxide. In those embodiments where the polyoxyalkylene glycol chain
 contains a mixture of units from different alkylene oxides, the
 arrangement of the different alkylene oxide units may be random or in
 blocks of the same alkylene oxide. The polyoxyalkylene diamine require
 sufficient alkylene oxide derived units so that polyoxyalkylene diamine
 and hydrophilic polyepoxides present render the final amine-terminated
 resin water soluble or miscible. Preferably, the polyoxyalkylene diamine
 has an average molecular weight of from 200 to 4000, and more preferably
 of from 300 to 3000, most preferably. Preferably the polyoxyalkylene
 diamine useful in the invention correspond to the Formula 16
 ##STR10##
 wherein:
 R.sup.10 is independently in each occurrence hydrogen, methyl or ethyl;
 R.sup.11 is independently in each occurrence a C.sub.1-10 straight- or
 branched-chain alkylene, C.sub.1-10 straight- or branched-chain
 alkenylene, or a C.sub.5-12 divalent cycloaliphatic moiety;
 R.sup.13 is independently in each occurrence a C.sub.1-10 straight- or
 branched-chain alkyl moiety or hydrogen;
 Z is independently in each occurrence oxygen or
 ##STR11##
 X is independently in each occurrence a straight- or branched-chain
 C.sub.1-6 alkyl moiety;
 c is independently in each occurrence 1 or greater;
 b is independently in each occurrence 2 or 3;
 f is independently in each occurrence from 2 to 4; and
 h is independently in each occurrence 0 or 1;
 with the proviso that for each
 ##STR12##
 unit if f is 2 and one R.sup.10 is ethyl, then the other R.sup.10 must be
 hydrogen, and if f is 3 or 4, R.sup.10 is hydrogen.
 Preferably Z is oxygen. Preferably X is a C.sub.2-4 alkylene moiety.
 Preferably R.sup.10 is hydrogen or methyl and more preferably hydrogen.
 Preferably R.sup.11 is a C.sub.1-10 straight- or branched-chain alkylene
 moiety and more preferably a C.sub.2-4 alkylene moiety. Preferably c is
 from 2 to 6 and more preferably from 2.6 to 3. Preferably b is 2.
 Preferably h is 0.
 Such polyoxyalkylene diamines are well known in the art. Examples of
 preferred polyoxyalkylene diamines are the polyamines available from
 Texaco Chemicals Company (Houston, Tex., USA) under the trade name
 JEFFAMINE, for example, JEFFAMINE D 400, JEFFAMINE D 2000.
 The additional amines which may optionally or alternatively be present
 include amines containing at least one primary or secondary amine moiety
 which are capable of reacting with an epoxy resin; preferably such
 compounds are sterically hindered. The term "sterically hindered" in
 reference to a polyamine means that the amine group is located on a
 secondary or tertiary carbon which is in a sterically hindered position.
 Preferably such polyamines correspond to Formulas 17 or 18
 ##STR13##
 wherein R.sup.13 is previously defined, R.sup.12 is independently in each
 occurrence cyclohexyl, substituted cyclohexyl, or a C.sub.1-50
 hydrocarbylene moiety, which may be substituted with a non-interfering
 substituent and which may contain one or more secondary amines, ether,
 amine or thioether moieties in the backbone. R.sup.12 is preferably
 cyclohexyl, or a C.sub.2-8 hydrocarbylene moiety, optionally containing
 amide or secondary amino moieties in the backbone. R.sup.13 is preferably
 hydrogen or a C.sub.1-4 straight- or branched-chain alkylene moiety. In
 Formula 16, R.sup.13 is most preferably hydrogen. In Formula 18, R.sup.14
 is preferably a C.sub.1-25 linear, branched, alicyclic or polyalicyclic
 moiety. Examples of preferred amines include t-octylamine,
 N,N'-di-tertiarybutyl ethylene diamine and 2,6-dimethylcyclohexylamine.
 These polyamines are included in the composition in sufficient amounts to
 enhance the final mechanical properties of the coatings prepared upon
 cure. If too much of certain polyamines are used the final resin may not
 be sufficiently emulsifiable in water.
 Polymeric epoxy emulsion (VII) as used herein refers to a dispersion of
 epoxy-terminated molecules as particles in water in the size range
 typified as an emulsion prepared as described in this invention. In
 general, it is preferable to produce resin emulsions with small droplet
 diameters of a median value of about 1.5 micrometers. Usually a
 distribution of droplet diameters is obtained for the polymeric epoxy
 emulsion particles of from 0.8 to 7.0 micrometers. Some settlement may
 occur on prolonged standing or when the emulsions are highly dilute: this
 settlement is easily reversible by thorough stirring at low shear, for
 example, hand stirring is sufficient for up to 20 liters.
 The polyhydroxy hydrocarbon (IX) means herein a compound with a hydrocarbon
 backbone and on average more than one primary or secondary hydroxy moiety,
 preferably two or more. Halogenated polyhydroxy hydrocarbon means herein a
 polyhydroxy hydrocarbon which is substituted with one or more halogens.
 The hydroxyl moieties may be bound to aromatic aliphatic or cycloaliphatic
 moieties. Among preferred classes of polyhydroxy hydrocarbons and
 halogenated polyhydroxy hydrocarbons are the bisphenols; halogenated
 bisphenols; hydrogenated bisphenols; novolac resins, that is, the reaction
 product of phenols and simple aldehydes, preferably formaldehyde; and
 polyalkylene glycols. The reaction product of phenol and an aldehyde,
 preferably formaldehyde, is a well-known product, as is the process for
 its production. Such a product is commonly referred to as a novolac resin.
 Optionally, the emulsifiable composition comprising reaction product (VII)
 may further comprise an organic solvent (X), present in sufficient amounts
 to stabilize the epoxy emulsion in water. Optionally, such solvent is
 present in amounts of up to 10 weight parts, more preferably 0 to 5
 weight, and most preferably from 0 to 1.5 weight parts of solvent per 100
 weight parts of reaction product (VII). Preferred solvents include glycols
 based on alkylene glycols, and ethers thereof, alkyl or
 hydroxyalkyl-substituted benzenes, lower alkanols, .gamma.-butyrolactone,
 .gamma.-caprolactone and n-methyl pyrrolidone. The preferred alkylene
 glycols are those based on ethylene, propylene, and butylene oxide. The
 glycol ethers are alkyl ethers of such glycols. Preferred glycols are
 those based on propylene oxide and butylene oxide, with preferred glycol
 ethers being C.sub.1-4 alkyl ethers of propylene and butylene glycols. The
 most preferred glycol ethers are the C.sub.1-4 alkyl ethers of propylene
 glycol. Examples of the preferred solvents are methyl ether of propylene
 glycol, benzyl alcohol, isopropyl alcohol, butyrolactone,
 .gamma.-caprolactone, n-methyl pyrrolidone, and xylene.
 Catalysts (XI) which may be employed to facilitate the preparation of
 reaction product (VIII) of the polyepoxide compound with the one or more
 polyhydroxy hydrocarbons are those known to those skilled in the art for
 the reaction of epoxy moieties with active hydrogen containing compounds.
 Examples of useful catalysts include zinc carboxylate, organozinc chelate
 compound, trialkyl aluminum, quaternary phosphonium and ammonium salts,
 tertiary amines and imidazole compounds. The catalyst is generally
 employed in an amount of from 0.01 to 2; preferably 0.02 to 1, most
 preferably 0.02 to 0.1, weight percent based on the combined weight of the
 polyepoxide compound (II) and the optional polyhydroxy hydrocarbons (IX)
 used.
 Preferable curing agents (XII) which may be used in this invention are
 those which are soluble or dispersible in the polymeric epoxy emulsion
 reaction product (VII) and which contain more than 2 active hydrogen atoms
 per molecule. Included as curing agents (XII) are diamines and polyamines
 or adducts of such polyamines with epoxy resin, such as for example a
 reaction product of an excess of equivalents of isophorone diamine with a
 diglycidyl ether of bisphenol A wherein such reaction product preferably
 has an amine equivalent weight of 115; modified polyamides and
 amidoamines, and arylic anhydrides. Preferred are the polyamines. Also
 useful as curing agents are aminoalkylated interpolymers of vinyl
 carboxylic acids, and salts thereof, as described in U.S. Pat. No.
 4,227,621 and the self-dispersing curing agents described in the copending
 application GB 9604297.3 filed Feb. 29, 1996. Preferred curing agents
 include aliphatic polyamines, polyglycoldiamines, polyoxypropylene
 diamines, polyoxypropylene-triamines, amidoamines, imidazolines, reactive
 polyamides, polycyclic polyamines, ketimines, arylaliphatic)polyamines
 (that is, xylylene-diamine), cycloaliphatic amines (that is,
 isophoronediamine or diamino-cyclohexane) methane diamine,
 3,3-dimethyl-4,4-diaminodicyclohexyl-methane, heterocyclic amines
 (aminoethyl piperazine), aromatic polyamines, (methylene dianiline),
 diamino diphenyl sulfone, mannich base, phenalkamines and
 N,N',N"-tris(6-aminohexyl) melamine. Example of more preferred curing
 agents include modified polyamide curing agents like Casamid.TM. 360
 (Anchor Chemicals Ltd., Manchester, United Kingdom), or Epilink.TM. DP 660
 (Akzo, Deventer, The Netherlands) which is an amine-epoxy adduct. Other
 useful hardeners may be of the Mannich base class which are reaction
 products between nonyl phenol, formaldehyde and a polyamine for example,
 xylylenediamine. Such a product is sold by Akzo under the trade name
 Epilink.TM. DP 500.
 The epoxy resin composition of this invention is contacted with sufficient
 curing agents to cure the resin. Preferably the ratio of (epoxy glycidyl
 ether) equivalents to equivalents of curing agent is from 0.5:1 and 2:1;
 more preferably 0.6:1.4 to 1.4:0.6; even more preferably 0.8:1.2 to
 1.2:0.8 and most preferably 0.9:1.1 to 1.1:0.9.
 The emulsions of this invention may include pigments, dyes, stabilizers,
 plasticizers and other conventional additives. Preferably the formulation
 dispersion or emulsion in water has a solids level of from 40 to 80
 percent, and most preferably from 50 to 70.
 When used to form a coating, the emulsified reactive polymer compositions
 of this invention are contacted with a substrate. Water and any cosolvents
 used are then evaporated off to leave a coating. The coating will cure at
 ambient conditions in several days. Elevated temperatures may be used to
 speed up the cure of the coating composition. Such curing conditions are
 well known to those skilled in the art. The coating composition may be
 contacted with the substrate by any means known in the art including
 spraying, pouring or roller-coating the formulation.
 Insofar as epoxy advancement reactions are carried out in order to produce
 an advanced polyepoxide, procedures for performing such reactions well
 known in the art are used: see "The Handbook of Epoxy Resins", H. Lee and
 K.
 Neville (1967), McGraw Hill, New York and U.S. Pat. Nos. 2,633,458;
 3,477,990; 3,821,243; 3,907,719; 3,975,397; and 4,071,477. Common
 catalysts for epoxy advancement reactions, and common chain regulators and
 chain terminators well known in the art may be employed.
 In producing coating formulations, the use of pigments, slip additives,
 fillers, dispersing aids, defoamers, leveling agents, air release agents
 and other additives commonly applied in the industry have been applied.
 Epoxy Emulsion Quality
 The quality of an applied and cured emulsified two-component epoxy binder
 system depends greatly on the quality of the emulsion, particularly on the
 droplet size and distribution. Emulsion quality particularly influences
 the film formation, drying time, water resistance, gloss, pigment binding
 capacity, yield, flexibility, adhesion and hardness.
 Compared with conventional solvent systems, water dispersed resins tend to
 foam more when they are produced and when they are applied. This
 undesirable build-up of foam may result from the impact of mechanical
 energy during emulsification procedures particularly when the process is
 not run under vacuum. Foam can lead to blemishes in appearance such as
 pitting, bubbles, and fish-eyes. The non-ionic emulsifiers in the
 experimental epoxy resins were selected also for their ability to furnish
 low foam emulsions. However, additives such as BYK 023 (Byk Chemie, Wesel,
 Germany) antifoaming agent, may be added to the epoxy-terminated species
 before they are emulsified. Defoamer should be added in a concentration of
 0.04 to 0.5 percent.
 Flocculation or aggregation of resin droplets can cause uneven and matted
 surfaces. The droplet size of the emulsion has a variable influence on
 different properties of the film.
 Properties like gloss, water-resistance, stability and pigment-binding,
 seem to suffer with increased droplet particle size while drying time,
 hold-out and brush ability improves with increased droplet particle size.
 Clearly a balance of properties is sought.
 In general it is preferable to produce resin emulsions with small droplet
 diameters of a medium value of about 1.5 micrometers. Usually a
 distribution of droplet diameter is obtained for the experimental epoxy
 resins of 0.8 and 7 micrometers. However, some settlement might occur upon
 prolonged standing and when the emulsions are highly diluted. Therefore
 thorough stirring of the emulsion is necessary before taking fractional
 amounts out of the container to avoid inconsistencies due to concentration
 differences.
 In one embodiment, this invention provides, as an aqueous dispersion, a
 blend of an aqueous epoxy-terminated polymeric amino-epoxy adduct emulsion
 (VII) and a curing agent (XII), the aqueous epoxy-terminated polymeric
 amino-epoxy adduct (VII) comprising the reaction product of from 30 to 90
 parts by weight, preferably 50 to 85 parts by weight, more preferably 60
 to 80 parts by weight of one or more aromatic polyepoxides (II) of average
 molecular weight greater than 300, from 2 to 50 parts by weight,
 preferably 5 to 30 parts by weight, most preferably 10 to 20 parts by
 weight of a polyoxypropylene diglycidyl ether (III) having an average
 molecular weight of 250 to 12,000 and from 2 to 50 parts by weight,
 preferably from 5 to 30 parts by weight, most preferably from 10 to 20
 parts by weight of an compound (V), the aqueous epoxy-terminated polymeric
 amino-epoxy adduct (VII) having an epoxy equivalent weight (EEW) based on
 solids of from 178 to 1000, preferably from 250 to 750, most preferably
 from 400 to 650. The aqueous epoxy-terminated polymeric amino-epoxy adduct
 emulsion is blended with a curing agent, the curing agent (XII) being
 present as an aqueous solution or dispersion, or the curing agent being
 dispersible in the aqueous epoxy-terminated polymeric amino-epoxy adduct
 emulsion, to produce an aqueous emulsified reactive polymer composition
 (I).
 In a further embodiment, the aromatic polyepoxides and polyoxypropylene
 diglycidyl ethers may be (co)-advanced with each other or with a
 polyhydric phenol or with an alcohol by standard means known to those
 skilled in the art to provide higher molecular weight epoxy-terminated
 species prior to reaction with the amine compound.
 A further embodiment is a process by which the aqueous emulsified reactive
 polymer composition is prepared. In this process, the polyepoxides and
 amines are mixed in the liquid phase at a temperature of between
 70.degree. C. and 135.degree. C., more preferably between 80.degree. C.
 and 130.degree. C., most preferably between 85.degree. C. and 125.degree.
 C. The reaction of the polyepoxides with the amines takes place at a
 temperature of between 80.degree. C. and 200.degree. C., more preferably
 between 80.degree. C. and 180.degree. C., and most preferably between
 80.degree. C. and 160.degree. C. The emulsification of the resulting
 product in water takes place at a temperature between 50 and 110.degree.
 C., more preferably between 50.degree. C. and 100.degree. C., most
 preferably between 50.degree. C. and 90.degree. C. To produce an aqueous
 epoxy-terminated polymeric amino-epoxy adduct emulsion, the aqueous
 epoxy-terminated polymeric amino-epoxy adduct emulsion and the curing
 agent is mixed at ambient temperature under conditions of low shear
 agitation. Generally, hand agitation or mixing in conventional equipment
 used in the art at less than 100 rpm (revolutions per minute) is
 sufficient to emulsify the amino-epoxy adduct and curing agent in water.
 Higher agitation speeds may be used, but are not required.
 Further embodiments are cured coatings derived from the ambient cure of the
 aqueous emulsified reactive polymer compositions. The stable
 epoxy-terminated emulsion as described above provides a stable emulsified
 reactive polymer composition, which, upon cure at a temperature between
 5.degree. C. and 35.degree. C., preferably between 10.degree. C. and
 30.degree. C., for a period of between 5 and 75 hours, preferably between
 10 and 50 hours, at a relative humidity of between 10 and 100 percent,
 preferably of between 25 and 60 percent, provides a glossy cured film
 exhibiting good cure properties, good Pendulum Hardness resistance and
 good chemical resistance.
 Clear coating formulations and pigmented formulated formulations were
 produced using methods common in the industry and well known to those
 skilled in the art.
 The test methods used in evaluating cure characteristics and coating
 properties are also common in the industry and well known to those skilled
 in the art. The specific test methods used are now referred to or
 described.
 Further embodiments are cured coatings derived from the ambient cure of the
 aqueous emulsified reactive polymer compositions. The stable
 epoxy-terminated emulsion as described above provides a stable emulsified
 reactive polymer composition, which, upon cure at a temperature between
 5.degree. C. and 35.degree. C., preferably between 10.degree. C. and
 30.degree. C., for a period of between 5 and 75 hours, preferably between
 10 and 50 hours, at a relative humidity of between 10 and 100 percent,
 preferably of between 25 and 60 percent, provides a glossy cured film
 exhibiting good cure properties, good Pendulum Hardness resistance and
 good chemical resistance.
 Clear coating formulations and pigmented formulated formulations were
 produced using methods common in the industry and well known to those
 skilled in the art.
 The test methods used in evaluating cure characteristics and coating
 properties are also common in the industry and well known to those skilled
 in the art. The specific test methods used are now referred to or
 described.
 Pigmented Formulations
 For the pigmented coating studies described in this invention a variety of
 paint was produced.
 First the curing agent and pigments were mixed at 2500 rpm in a Dispermat
 FT (VMA Getzmann, Reichshof, Germany) for 5 minutes. To the pigment paste,
 glass beads of 2 mm diameter had been added so that the pigment paste to
 glass bead weight ratio was 1:1. Then milling was carried out under water
 cooling for 25 minutes at 2500 rpm. After the milling water and defoamer
 had been added to the mill base, the pigmented mixture was allowed to be
 stirred for another 5 minutes at 1000 rpm. Grindometer readings were taken
 from the pigment paste both after milling, and also on the following day
 in order to reconfirm the values. In some cases air bubbles contained in
 the paste prevented an immediate measurement. The average particle size of
 the pigment paste was ca. 10 micrometers.
 Coating Application
 Coatings were either drawn down with an Erichsen applicator (Erichsen,
 Hemer-Sundwig, Germany) or air-sprayed to a predetermined film thickness
 of 50 to 60 micrometers in a one-coat application for physical tests
 (curing rate, and gloss, flexibility,). All chemical resistance tests were
 conducted on one coat applications of ca. 90 micrometers dry film
 thickness.
 Substrates
 Three substrates were employed in the testing.
 1. Sand blasted cold-rolled steel with a 40 micrometer peak to valley
 profile for salt-spray resistance. This was conducted on two-coat
 applications. Buildup on each coat was approximately 50 to 60 micrometer
 thickness and 1 day was allowed between coats for curing at ambient
 conditions.
 2. Bonder steel 26-60-.degree. C. (190 mm.times.105 mm.times.0.75 mm) for
 physical tests.
 3. Glass plates to follow gloss and transparency during pot life and film
 formation.
 Curing Conditions Used for the Studies
 Test panels were allowed to cure at ambient conditions (23.degree. C./45 to
 55 percent RH) on the following schedule prior to testing:
 1. Physical properties--7 days
 2. Resistance properties--three weeks (minimum) exceptions to these
 conditions and schedules are obvious and noted in the data tables.
 3. Cure under adverse conditions examines curing characteristics at
 10.degree. C. and at very high humidity of ca. 80 percent RH (relative
 humidity). In this case panels are examined after removal from the test
 environment to determine any lasting adverse effects like flash rusting.
 Physical Tests
 Through Film Drying Time (TFDT)
 Through film drying time is a measure of the various stages and rates of
 film formation in the drying or curing of organic coatings for the purpose
 of comparing types of coatings or ingredient changes, or both. The
 procedure followed is, in principle, covered by ASTM D1640-83, however
 here an Erichsen drying time recorder (Model 509, Erichsen, Hemer-Sundwig,
 Germany) is used. This is a recorder which pulls a needle with a constant
 speed over a glass bar on which a coating has been drawn.
 Methyl Ethyl Ketone (MEK) Resistance/Double Rubs
 This test monitors the resistance of a coating against MEK in the initial
 phase of cure as a function of the time elapsed after application.
 Coatings are prepared on steel and after the coating is tack-free, the dry
 film thickness of the system to be tested and a reference system is
 determined. The dry film thickness should differ by not more than 10
 percent. The actual test is then performed as follows: the flat end of a
 500 g hammer is covered with a piece of cotton-wool. The cotton-wool is
 soaked with MEK and a hammer is brought to one side of the panel. The
 hammer is moved forth-and-back over the whole coating, being one double
 rub. Care has to be taken not to put any additional pressure on the
 hammer. After every 20 double rubs the cotton-wool is re-soaked with MEK.
 The procedure is repeated until the coating is rubbed off to such an
 extent that the panel becomes visible or other defects occur. This test is
 repeated daily until the application withstands 100 double rubs without
 visible effect. The difference in MEK double rub development gives an
 indication of the rate at which cross-linking is achieved.
 Gloss
 Readings are made using a gloss meter (Type L, Dr. Lange, Berlin, Germany)
 and measured at 20.degree., 60.degree.and 80.degree.angles of reflection.
 Pendulum Hardness Development
 This test method uses a pendulum damping tester as a measure of the rate of
 cure by means of hardness development of organic coatings that have been
 applied to acceptable plane rigid surfaces. The test follows the proposal
 by ASTM D4366-84 method B: "Hardness of organic coatings by pendulum
 (Persoz) damping test".
 Sudden Impact Resistance
 Impact tests were conducted using a Gardner Heavy Duty Variable Impact
 Tester. Reverse (substrate between the impacter and the test coating) and
 direct (impacter applied to coating) impact tests were conducted. Results
 are reported as the force (Joules) necessary to cause failure (cracking)
 of the film; therefore, the higher the reading--the more flexible the
 film.
 Film Thickness
 This test is performed following the guide-lines by ASTM DI 186-81;
 "Non-destructive measurement of dry film thickness of non-magnetic
 coatings applied to ferrous base" (11).
 Adhesion
 The cross-cut test is a simple empirical test to determine the adhesion of
 a one or more coat system on its substrate as well as the intercoat
 adhesion. This test was performed in accordance with ASTM D3359-83:
 "Measuring adhesion by tape test", method B. This method covers a
 procedure for assessing the adhesion of coating films to metallic
 substrates by applying and removing tape over cuts made in the film. In
 the examples described in this report TESAK 4124 tape is used.
 Resistance Against Slow Deformation/Erichsen Indentation
 This empirical test gives an indication about the resistance of a coating
 system against cracking and/or loss of adhesion due to deformation of the
 substrate. The test is performed in accordance with DIN/ISO 1520 of
 February 1982: "Tiefungspruefung".
 Chemical Resistance
 This test gives a quick indication about the chemical resistance and is to
 be used on a relative basis only.
 A piece of cotton-wool of approximately 1 cm diameter is saturated with the
 chemical against which the coating has to be tested. The chemicals for
 this purpose were:
 Deionized water, ethanol, xylene, toluene, gasoline, aqueous sodium
 hydroxide solution (10 percent by weight.), aqueous acetic acid solution
 (10 percent by weight.), aqueous hydrochloric acid solution (10 percent by
 weight.) and aqueous sulfuric acid solution (10 percent by weight.). The
 cotton-wool is covered with a glass lid of 50 mm diameter and a height of
 30 mm which is sealed with silicon grease to the coating. Hourly or daily
 the appearance of the coating is judged by means of determining the degree
 of blistering, and discoloration. The test is performed for one week. The
 results of blistering and visual surface test like color changes or
 softening have been monitored and rated on a scale of 0 (poorest) to 10
 (best).
 Salt Spray
 Tests were conducted in a salt-fog cabinet saturated with a fog from a 5
 percent salt solution. Test temperature was 55.degree. C. The panel was
 inscribed with the Greek letter lambda through to the substrate. Panels
 were examined after 500, 750 and 1000 hours exposure. Failure to protect
 the substrate is indicated by severe blistering or creepage from the
 scribe in excess of 6 mm.
 Humidity Resistance
 Tests were conducted in a 40.degree. C. and 100 percent humidity cabinet.
 Examinations occurred after 550, 750 and 1000 hours exposure. Failure to
 protect the substrate, was indicated by blistering.
 The following examples are included for illustrative purposes and are not
 intended to limit the scope of claims herein. All parts and percentages
 stated herein are by weight, unless otherwise indicated.

EXAMPLE 1
 A one liter, five-neck round-bottom glass reactor equipped with a nitrogen
 inlet, water cooled condenser and metal anchor design agitator driven by
 an electric motor was used. A 250 mL dropping funnel was employed.
 Temperature control was provided by a thermocouple, heating mantle and
 temperature controller.
 Diglycidyl ether of Bisphenol-A having an epoxy equivalent weight (EEW) of
 180 (A, 360 g) and a polyoxyalkylene diglycidyl ether having an epoxy
 equivalent weight of 5450 and an ethylene oxide/propylene oxide mole ratio
 of 5:1 (B, 60 g) were charged into the reactor and heated within 30
 minutes to 100.degree. C. under a nitrogen blanket. Agitation was applied
 after B was molten, and 2,6-dimethyl cyclohexylamine (C, 80 g) added under
 agitation. The reaction mixture was heated to 120.degree. C. whereupon an
 exothermic reaction ensued which peaked at ca. 160.degree. C. The reaction
 mixture was allowed to react for two hours. The resultant epoxy resin was
 a non-tacky semi solid, exhibiting good solubility in acetone. The resin
 was cooled to 100.degree. C., and water (500 g) added continuously over 90
 minutes while maintaining a temperature of 85.degree. C. to 95.degree. C.
 during addition of the first 250 mL and 70.degree. C. to 75.degree. C.
 during addition of the second 250 mL of water. The resulting emulsion was
 kept at 60.degree. C. for a further two hours, cooled to below 30.degree.
 C. and bottled. The epoxy emulsion had a solids content of 50 percent, a
 viscosity of ca. 7,500 mPa.s at 23.degree. C. and an EEW of ca. 1250.
 Poly(methylenecyclohexanamine) in benzyl alcohol with an amino hydrogen
 equivalent weight (AHEW) of 108 (Ancamine 2280, Anchor Chemicals UK, 8.4
 g) was emulsified into the epoxy emulsion prepared above (100 g) by hand
 stirring. Water (15 mL) was then added for dilution. Films were cast from
 this blend on Bonder 26 60 0 C. steel panels using a 200 micrometer draw
 down bar. The coatings became tack free after one hour, and withstood 100
 MEK double rubs after 24 hours cure at 23.degree. C., and 200 MEK double
 rubs after 7 days cure at 23.degree. C. A drop of water placed on this
 coating after 7 hours did not attack or dissolve the film: the adhesion of
 the coating was excellent. After 7 days cure at room temperature, the
 coating formed developed an impact of 17 Joules and an Erichsen
 indentation value of 9.
 EXAMPLE 2
 A reaction sequence, reactants and equipment similar to those used in
 Example 1 were employed. Diglycidyl ether of bisphenol-A having an epoxy
 equivalent weight (EEW) of 180 (A, 387 g) and a polyoxyalkylene diglycidyl
 ether having an epoxy equivalent weight of 5450 and an ethylene
 oxide/propylene oxide mole ratio of 5:1 (B, 63 g) were charged into the
 reactor and heated within 30 minutes to 100.degree. C. under a nitrogen
 blanket. Agitation was applied after B was molten, and tert-octylamine (C,
 80 g) added under agitation. The reaction mixture was heated to
 120.degree. C., whereupon an exothermic reaction ensued which peaked at
 ca. 145.degree. C. The reaction mixture was allowed to react for two
 hours. The resin was cooled to 70.degree. C., and water (470 g) added over
 one hour while maintaining a temperature of 50.degree. C. to 70.degree. C.
 The resulting emulsion had a solids content of 52.5 percent, a viscosity
 of 10,000 to 15,000 mPa.s at 23.degree. C. and an EEW of ca. 1075.
 This advanced epoxy emulsion was pigmented as shown in Table I and cured
 with a 1:1 by weight blend of the relatively hydrophobic curing agents
 polyamidoamide Versamid 140 (AHEW 125, Cray Valley, Newport, Wales, United
 Kingdom) and polyoxypropylenediamine with a molecular weight of 400
 (Jeffamine 400, Texaco Chemicals Company). The pigmented systems described
 in Table I were further diluted with water, and sprayed on Bonder 26 60 0C
 panels. The paint formulations dried within 30 minutes at 23.degree. C.:
 after 7 days cure at 23.degree. C. the coated panels withstood more than
 200 MEK double rubs and had excellent condensed water resistance (7 days
 exposure to condensed humidity at 55.degree. C.).
 TABLE I
 Pigmented Water Emulsified Reactive Epoxy Polymer Comparisons
 PAINT PAINT
 I* 2**
 PROCEDURE/INGREDIENTS Weight Weight
 Mix under Agitation
 Epoxy Emulsion (EEW 1075, Non-Volatile Content 49.78 41.82
 52,5%) - Example 2
 Water, demineralized. 10.23 16.10
 Iron oxide red (Bayferrox 130M/Bayer AG, -- .81
 Leverkusen, Germany)
 Pigment mixture of Fe.sub.2 O.sub.3 and Mn.sub.2 O.sub.3 (Bayferrox 1.14
 --
 303T/Bayer AG)
 Iron oxide yellow (Bayferrox 920/Bayer AG) -- .81
 Titanium dioxide (Finntitan RR2/Kemira, 3.73 11.53
 Pori, Finland)
 Talcum - contains magnesite MgCO.sub.3 (Talcum 1.82 --
 AT Extra/Norwegian Talc Deutschland GmbH, Bad
 Soeden-Salmuenster, Germany)
 Calcium carbonate (Durcal 10/OMYA GmbH, 17.54 --
 Koeln, Germany)
 Muscovite-mica (Micro Mica W 1/Norwegian Talc, 9.37 --
 Deutschland GmbH)
 Precipitated barium sulfate (Blanc Fix N/Sabed, -- 11.53
 Massa, Italy)
 Zinc phosphate (Sicor ZNP/S/BASF AG, -- 11.53
 Ludwigshafen, Germany)
 Emulsion of hydrophobic non-volatile, emulsifiers 0.60 .59
 and anti-foaming polysiloxane
 (BYK 203/Byk-Chemie GmbH, Wesel, Germany)
 Disperse on a horizontal pearl mill under
 cooling (&lt;40.degree. C.) to &lt;10 .mu.m
 Add under agitation
 Polyaminoamide (Versamid 140/Cray Valley) 5 4.40
 Polyoxypropylene diamine (Ancamine 480/Anchor .79
 Chemical)
 Catalyst blend at AHEW ca. 124 (Ancamine K 54/
 Anchor Chemical)
 Leveling agent (BYK S 715/Byk-Chemie --
 GmbH) 81
 Polyether modified methylalkyl- --
 polysiloxane-copolymer (BYK A 525/ 81
 Byk-Chemie GmbH)
 TOTAL AMOUNT 00.00 1 100.00
 *Paint I = grey paint
 **Paint 2 = rose red paint
 EXAMPLE 3
 Following the method of Example 1, diglycidyl ether of Bisphenol-A having
 an epoxy equivalent weight (EEW) of 180 (A, 141.6 g), bisphenol-A (B, 44.5
 g), a polyoxyalkylene diglycidyl ether having an epoxy equivalent weight
 of 5450 and an ethylene oxide/propylene oxide mole ratio of 5:1 (C, 64.7
 g), p-tert-butyl phenol (D, 7.6 g) and methoxypropanol (E, 4.2 g) were
 charged into the reactor and heated within 30 minutes to 80.degree. C.
 under a nitrogen blanket. Agitation was applied, the mixture was heated to
 90.degree. C., and ethyltriphenylphosphonium acid acetate 70 percent
 active in methanol (F, 0.4 g) was added under agitation. The mixture was
 heated to 115.degree. C. whereupon an exothermic reaction ensued which
 peaked at ca. 140.degree. C. The reaction mixture was then further heated
 at 145.degree. C. for 2 hours to yield an advanced epoxy resin with an
 epoxy equivalent weight of 760.
 This resin was cooled to 90.degree. C. and the polyoxypropylenediamine with
 a molecular weight of 400 (Jeffamine D400, G, 163.6 g) and isophorone
 diamine (H, 67.4 g) added under agitation. All heating was switched off,
 and the reaction contents cooled to about 70.degree. C. before an
 exothermic reaction took place which peaked out at 86.degree. C. The
 reaction mixture was heated slowly to 120.degree. C. over 45 minutes,
 maintained at this temperature for 1.5 hours and cooled to 99.degree. C.
 over 15 minutes. Water (404.0 g) was continuously added over 35 minutes
 with agitation while maintaining a temperature of at least 65.degree. C.,
 and the resulting emulsion stirred at 60.degree. C. for 30 minutes before
 cooling to below 30.degree. C. and bottling.
 The resulting emulsion had a solids content of 55 percent, a viscosity of
 ca. 5,000 mPa.s at 23.degree. C., an amino hydrogen equivalent weight
 (AHEW) of ca. 315 and a pH of 11.4.
 EXAMPLE 4
 Poly (methylenecyclohexamine) (Ancamine X2280/Anchor Chemical, 85 g) was
 intimately mixed at room temperature with dispersing aid Disperbyk 182
 (Byk Chemie, 10.5 g) and tris-2,4,6-dimethylaminomethylphenol (Ancamine
 K54/Anchor Chemicals, 4.5 g).
 EXAMPLE 5
 A reaction sequence, reactants and equipment similar to those used in
 Example 1 were employed. Diglycidyl ether of bisphenol-A having an epoxy
 equivalent weight (EEW) of 180 (A, 235 g), a polyglycidyl ether of a
 bisphenol-F with a functionality of 2.2 and an EEW of 168 (B, 100 g), a
 polyoxyalkylene diglycidyl ether having an epoxy equivalent weight of 5450
 and an ethylene oxide/propylene oxide mole ratio of 5:1 (C, 60 g) and
 bisphenol-A (D, 42.5 g) were charged into the reactor and heated within 30
 minutes to 80.degree. C. under a nitrogen blanket. Agitation was applied,
 the mixture was heated to 90.degree. C., and ethyltriphenylphosphonium
 acid acetate 70 percent active in methanol (E, 0.6 g) was added under
 agitation. The mixture was heated to 115.degree. C. whereupon an
 exothermic reaction ensued which peaked at ca. 165.degree. C. The reaction
 mixture was then further heated at 145.degree. C. for 1.5 hours to yield
 an advanced epoxy resin with an epoxy equivalent weight of 288. This resin
 was cooled to 100.degree. C. and a polyoxypropylenediamine with a
 molecular weight of 2000 (Jeffamine D 2000, F, 62.5 g) added under
 agitation. The reaction mixture was allowed to react at between 92 and
 95.degree. C. for one hour.
 Water (500.0 g) was continuously added over one hour with agitation while
 maintaining a temperature of at least 70.degree. C., and the resulting
 emulsion stirred at 60.degree. C. for one hour before cooling to below
 30.degree. C. and bottling.
 The resulting emulsion (Example 5) had a solids content of 50 percent, a
 viscosity of 2,000 to 8,000 mPa.s at 23.degree. C. and an EEW of ca. 718
 (based on emulsion).
 Formulations to produce clear coats containing the epoxy resin emulsion
 prepared as described above separately with the three hardeners (Example
 5.1) a polyamino epoxy adduct solution in water at 70 percent solids and
 AHEW 200 as solution (Anquamine 401/Anchor Chemical), (Example 5.2) the
 amine curing agent the preparation of which was described in Example 3 and
 (Example 5.3) the amine curing agent the preparation of which is described
 in Example 4, are described in Table II as Systems 1 to 3 respectively,
 and the clear coat properties obtained by curing these systems at
 23.degree. C. are described in Table III. Pigmented paint formulations
 based on the resin and hardener components described in this Example 5 are
 described in Tables IV, V and VI and a comparison of general properties of
 the paints produced from these formulations by curing separately at
 23.degree. C. and at 10.degree. C. are shown in Table VII. Corrosion
 resistance properties for the paints produced from these formulations by
 curing at 23.degree. C. are shown in Table XIII.
 TABLE II
 Clear Coat Formulations
 INGREDIENTS IN SYSTEM SYSTEM SYSTEM
 TS BY WEIGHT 1 2 3
 Mix under agitation for 15 minutes
 Epoxy Emulsion - Example 5 721.7 618.1 716.0
 Curing Agent 5 (1) 198.8 -- --
 Curing Agent 5 (2) -- 267.7 --
 Curing Agent 5 (3) -- -- 142.0
 Tris-2,4,6-dimethylaminophenol -- 13.9 --
 (Catalyst Ancamine K54/
 Anchor Chemicals)
 Dilute with demineralized water 79.5 100.3 142.0
 Viscosity at 23.degree. C. [mPa.s] ca. 3000 ca. 4500 ca. 2500
 Application solids, % 50.0 50.0 50.0
 Amine-H to epoxy equivalent 1:1 1:1 1:0.9
 wt. ratio
 TABLE III
 Clear Coat Performance Properties
 SYSTEM SYSTEM SYSTEM
 FEATURE 1 2 3
 I) Wet varnish
 Per cent benzyl alcohol at zero zero ca. 7
 application viscosity
 Pot life [h] max. 3 1.5 max. 2.5
 Through film drying time .about.6 .about.8 .about.6
 (TFDT) [h]
 II) Dry film (on Bonder 26-60-0C)
 Film Thickness [.mu.m] 43 57 45
 Persoz hardness [s]
 1 d RT cure 40 60 90
 7 d RT cure 90 159 236
 Film appearance Hazy Sl. Hazy High
 clarity
 Cross-hatch adhesion 100 100 100
 [% remain]
 7 d RT cure
 Erichsen indentation [mm] &gt;10 9 9
 7 d RT cure
 Resistance to water-spotting poor good excellent
 1 d RT cure
 Resistance to MEK rubs &gt;100 100 &gt;150
 1 d RT cure
 TABLE IV
 Paint Formulation 1
 PROCEDURE/INGREDIENTS WEIGHT
 Mix under agitation
 Aqueous Comparative Example 5 312.70
 Finntitan RR2 (Titanium dioxide iron Kemira) 101.72
 Sicor ZNP/S (Zinc phosphate from BASF) 101.72
 Blanc fix N (barium sulfate from Solvay SA, B-1050 101.72
 Brussels, Belgium)
 Bayferrox 130M (Iron oxide, red from Bayer AG) 7.13
 Bayferrox 920 (Iron oxide, yellow from Bayer AG) 7.13
 Demineralized water 86.36
 Byk 023 (Defoamer from Byk Chemie GmbH) 4.81
 Disperse on a horizontal pearl mill under cooling
 (&lt;40.degree. C.) to &lt;10 .mu.m
 Add under agitation a pre-solution containing:
 Epoxy Curing Agent for Example 5 (1) 87.57
 Demineralized Water 189.13
 Add demineralized water for required application viscosity 1000.00
 Parameters
 Solids content: 53.7
 Pigment/binder ratio: 1:0.7 (solids)
 Pigment Volume Concentration (PVC) 30.0%
 TABLE V
 Paint Formulation 2
 PROCEDURE/INGREDIENTS WEIGHT
 Mix under agitation
 Curing Agent from Example 5 (2) 124.77
 Catalyst Ancamine K54 (Anchor Chemicals Ltd.) 8.76
 Finntitan RR2 (Titanium dioxide) 112.77
 Sicor ZNP/S (Zinc phosphate) 112.77
 Blanc fix N (Barium sulphate) 112.77
 Bayferrox 130M (Iron oxide, red) 7.90
 Bayferrox 920 (Iron oxide, yellow) 7.90
 Demineralized water 65.32
 Byk 033 (Defoamer) 2.22
 Disperse on a horizontal pearl mill under cooling
 (&lt;40.degree. C.) to &lt;10 .mu.m
 Add under agitation
 Aqueous Epoxy comparative for Example 5 287.92
 Demineralized Water 156.90
 Add demineralized water for required application viscosity 1000.00
 Parameters
 Solids content: 57.6
 Pigment/binder ratio: 1:0.7 (solids)
 PVC 30%
 TABLE VI
 Paint Formulation 3
 PROCEDURE/INGREDIENTS WEIGHT
 Mix under agitation
 Aqueous Epoxy comparative from Example 5 443.66
 Finntitan RR2 (Titanium dioxide) 76.01
 Sicor ZNP/S (Zinc phosphate) 76.01
 Blanc fix N (Barium sulphate) 76.01
 Bayferrox 130M (Iron oxide, red) 5.32
 Bayferrox 920 (Iron oxide, yellow) 5.32
 Demineralized water 31.14
 Byk 023 (Defoamer) 4.65
 Disperse on a horizontal pearl mill under cooling
 (&lt;40.degree. C.) to &lt;10 .mu.m
 Add under agitation
 Curing Agent from Example 5.3 88.98
 Then add demineralized water 192.90
 Add demin. water for required application viscosity 1000.00
 Parameters
 Solids content: 55.0
 Pigment/binder ratio: 1:1.3
 PVC 20%
 TABLE VII
 GENERAL PROPERTIES PAINT 1 PAINT 2 PAINT 3
 Water-borne Paints 1, 2 and 3 - Comparison of
 General Properties (Cure at 23.degree. C.)
 Contains epoxy hardener 5.1 5.2 5.3
 Pigment volume concentration of 30 30 20
 point [%]
 Coating thickness [.mu.m] ca. 55 ca. 55 ca. 55
 Drying time, tack-free [h] 1.8 2.5 2.8
 Gloss 20.degree./60.degree./80.degree. 1/2/33 1/6/27 9/50/86
 MEK resistance [DR] 1. day cure &gt;100 80 &gt;100
 Pendulum hardness 133 137 198
 according to Persoz [s]
 Cross-cut adhesion tape test 100 100 100
 remain [%]
 Erichsen indentation [mm]
 7. day cure 5.5 3.5 5.0
 14. day cure 3.3 3.4 4.5
 Water-borne Paints 1 , 2 and 3 - Comparison of General Properties
 (Cure at 10.degree. C./80% RH)
 Contains epoxy hardener 5.1 5.2 5.3
 PVC of paint [%] 30 30 20
 Coating thickness [.mu.m] ca. 55 ca. 55 ca. 55
 Gloss 20.degree./60.degree./80.degree. 1/3/36 3/22/50 14/62/91
 MEK resistance [DR] 7 days cure &gt;100 &gt;100 &gt;100
 Pendulum hardness according to 68 76 111
 Persoz [s]
 Cross cut adhesion tape test 100 100 100
 remain [%]
 Erichsen indentation [mm] 6.1 3.9 8.7
 TABLE VIII
 Corrosion Resistance Paint 1, 2 and 3
 PROPERTIES PAINT 1 PAINT 2 PAINT 3
 Humidity ASTMD 4885-86A 0 5 7
 7 days constant at 55.degree. C. blisters
 [10 = best]
 Adhesion after 24 h recovery at 0 99 99
 23.degree. C./50% RH tape, remain [%]
 Salt spray - ASTM (B-117-730* [H] 350 500 1000
 Scripe creep [mm] ca.2 0 0
 Scripe blisters [10 = best] 4 4 9
 Surface blisters [10 = best] 4 4 9
 Surface corrosion none none none
 *Determine on 40 .mu.m Sand Blasted Steel with peak to valley ratio of
 maximum 40 .mu.m, with 50 .mu.m first coat and 60 .mu.m second coat
 EXAMPLE 6
 A reaction sequence, reactants and equipment similar to those used in
 Example 1 were employed. A polyglycidyl ether of a phenolic novolac with a
 functionality of 3.6 and an EEW of 178 (A, 390 g), and a polyoxyalkylene
 diglycidyl ether having an epoxy equivalent weight of 5450 and an ethylene
 oxide/propylene oxide mole ratio of 5:1 (B, 60 g) were charged into the
 reactor and heated to 90.degree. C. under a nitrogen blanket. Agitation
 was applied, the mixture was heated at 90.degree. C. for a further 15
 minutes and a polyoxypropylenediamine with a molecular weight of 2000
 (Jeffamine 2000, C, 50.0 g) added under agitation. The temperature dropped
 to 84.degree. C. and the mixture became turbid. The reaction mixture
 underwent an exothermic reaction to yield a clear solution at 90.degree.
 C. The mixture was heated to 100.degree. C. and maintained at this
 temperature for 15 minutes before water (250.0 g) was continuously added
 over 30 minutes with agitation while maintaining a temperature of
 85.degree. C. to 95.degree. C. The mixture was maintained at 90.degree. C.
 for 15 minutes before water (118.0 g) was continuously added over 15
 minutes with agitation while maintaining a temperature of 70.degree. C. to
 80.degree. C. The mixture was cooled to 50.degree. C. and maintained at
 this temperature for 90 minutes before cooling to below 30.degree. C. and
 bottling.
 The resulting emulsion had a solids content of 57.5 percent, a viscosity of
 2,500 mPa.s at 23.degree. C. and an EEW of ca. 415.
 A water-emulsified reactive polymer composition was produced by dispersing
 the amine curing agent, the preparation of which is described in Example 4
 (13 g) with the epoxy-functional emulsion prepared as described above (42
 g).
 Wet coatings were cast on glass plates, and on Bonder steel panels 26 60 0
 C. at 200 micrometer wet thickness. The through film drying time of the
 film was ca. 2 hours, when cured at 23.degree. C. Water, acid and solvent
 resistance of the cured coatings was much better than that normally
 obtained from water emulsified reactive polymer compositions derived from
 water-dispersed epoxy resins and amine curing agents. Specifically, these
 films exhibited faster cure time of ca. 3 hours than the ca. 12 hours of
 typical water dispersed bisphenol-A type liquid epoxy resin systems: these
 films described in Example 8 also had a solvent resistance some two to
 three times better and a water spotting resistance some four times better
 than typical water-dispersed bisphenol-A type liquid epoxy resin systems.
 EXAMPLE 7
 A diglycidyl ether of bisphenol-A having an epoxy equivalent weight (EEW)
 of 510 (A, 174 g), a diglycidyl ether of bisphenol-A having an epoxy
 equivalent weight (EEW) of 182 (B, 126 g), and a polyoxypropylene
 diglycidyl ether with EEW 328 (D.E.R..TM. 732, trademark of The Dow
 Chemical Company, C, 300 g) were mixed into a 1 litre vessel, held in an
 oven at 80.degree. C. for one hour and thoroughly mixed until a clear,
 homogeneous mixture was formed.
 EXAMPLE 8
 A reaction sequence and equipment similar to those used in Example 1 were
 employed. A polyoxyalkylene diglycidyl ether having an epoxy equivalent
 weight of 5450 and an ethylene oxide/propylene oxide mole ratio of 5:1 (A,
 71.5 g) and isophoronediamine (B, 187 g) were added to the reactor and
 heated over a period of 20 minutes to 75.degree. C. Agitation was started
 and the mixture heated to 90.degree. C. and maintained at this temperature
 for 15 minutes. The polyepoxide blend produced in Example 7 (291.5 g) was
 added at a temperature of 90 to 95.degree. C. over a period of 40 minutes,
 and the mixture maintained at 90.degree. C. for a further 90 minutes. The
 contents were cooled to 80.degree. C. and water (450 g) added over 45
 minutes with agitation while maintaining the temperature of the mixture
 above 50.degree. C. After water addition was complete, the resultant
 emulsion was stirred for a further one hour while maintaining the
 temperature between 45.degree. C. and 50.degree. C., before cooling to
 30.degree. C. and bottling. The polymeric aqueous dispersed curing agent
 exhibited an AHEW of 285 to 315.
 EXAMPLE 9
 A reaction sequence and equipment similar to those used in Example 1 were
 employed. A polyoxyalkylene diglycidyl ether having an epoxy equivalent
 weight of 5450 and an ethylene oxide/propylene oxide mole ratio of 5:1 (A,
 65 g) and N,N'-di-tert-butylethylenediamine (B, 84 g) were charged into
 the reactor and heated to 75.degree. C. under a nitrogen blanket.
 Agitation was applied, the mixture was heated at 135.degree. C. over 30
 minutes and maintained at this temperature for an additional 15 minutes. A
 polyoxypropylene diglycidyl ether with an EEW of 328 (D.E.R..TM. 732, C,
 35 g) and a diglycidyl ether of bisphenol-A having an epoxy equivalent
 weight (EEW) of 180 (D, 316 g) were added under agitation and the
 temperature raised to 145.degree. C. and maintained at this temperature
 for 2 hours. The mixture was then cooled to 90.degree. C. before water
 (500.0 g) was continuously added over a period of 45 to 60 minutes with
 agitation while maintaining a temperature of at least 50.degree. C. The
 mixture was maintained at 50.degree. C. for an additional 30 minutes
 before cooling to below 30.degree. C. and bottling.
 The resulting emulsion had a solids content of 50 percent, a viscosity of
 500 to 1000 mpa.s at 23.degree. C. and an EEW of ca. 1000 to 1200. The
 emulsion was blended in a stoichiometric ratio of 1:1 with the polymeric
 epoxy-amino adduct emulsion the preparation of which is described in
 Example 8 and cured at temperatures of 10.degree. C. and higher to yield
 coatings exhibiting a Persoz hardness of 90 and an adhesion of 100 percent
 after 24 hours cure at 23.degree. C., and an Erichsen indentation of 6 and
 a resistance to over 100 MEK double rubs after 7 days cure at 23.degree.
 C. A rapid through film drying time is a feature of the systems prepared
 from the epoxy emulsion described in Example 9.
 COMATIVE EXAMPLE 10
 Polyethylene glycol with an average molecular weight (Mw) of 3000
 (technical grade, 150 g) and a bisphenol-A based polyglycidyl ether with
 an epoxy equivalent weight of 185 (18.5 g) were heated to 100.degree. C.
 and diluted under agitation with boron trifluoride etherate (0.9 g)
 diluted to 5 weight percent with dioxane. The mixture was heated to
 130.degree. C., and maintained at this temperature until the ensuing
 reaction had ceased, as witnessed by an increase in the epoxy equivalent
 weight. The epoxy equivalent weight of the product A was ca. 360,000. A
 bisphenol-A based polyglycidyl ether with an epoxy equivalent weight of
 183 (325 g), bisphenol-A (98 g), the adduct A (27 g) and
 triphenylphosphine (750 mg) were mixed in a two-liter three-necked flask
 equipped with a thermometer, an agitator, a reflux condenser and a
 dropping funnel and heated at between 150.degree. C. to 160.degree. C.
 until an epoxy equivalent weight of 490 to 500 was obtained. The mixture
 was cooled and diluted with benzyl alcohol (27 g) and methoxypropanol (60
 g). The temperature was reduced to below 100.degree. C. and water (105 g )
 was added continuously over a period of 5 to 30 minutes while maintaining
 an agitator speed of 800 rpm and allowing the temperature to fall to
 between 70.degree. C. and 60.degree. C. An aqueous dispersion was obtained
 which was further diluted with water (173 g). The dispersion had a solids
 content of 55.7 percent and a viscosity of 11,700 mPa.s. A
 water-emulsified reactive epoxy polymer composition can be prepared from
 this dispersion by the addition, under agitation, of any common amine
 hardener suited for curing aqueous systems.
 COMATIVE EXAMPLE 11
 Isophorone diamine (26 g) was added to a three-necked glass flask equipped
 with a thermometer, an agitator and a condenser, and the contents were
 thoroughly agitated while maintaining a temperature of between 40.degree.
 C. to 50.degree. C. A polyglycidyl ether, having an epoxy equivalent
 weight of 1980 obtained from one mole of propylene oxide/ethylene oxide
 random polymer type polyether polyol PR-3009 (Asahi Denka Kogyo K. K.)
 having a molecular weight of 3,000 and an ethylene oxide content of 85
 percent by weight and 2.2 moles of epichlorohydrin, (13 g) and the
 hydrophobic epoxy compound EP-4901(EEW 182, Asahi Denka Kogyo K. K., 12 g)
 were added slowly while checking heat generation. The reaction was allowed
 to take place over two hours at 90.degree. C., and water (13 g) was added
 to obtain the self-emulsifying activated curing agent (X). Adeka resin
 EP-4200 (Asahi Denka Kogyo K. K., EEW 190, 10 g) the self-emulsifying
 activated curing agent X (7 g) and water (10 g) were mixed and cured. The
 film performance was tested to give the following results. Film condition
 after 24 hours was "good," `pencil hardness was "H,"` water resistance
 after 7 days of soaking was "good" and adhesion (mortar board checkerboard
 test) was 100/100.
 COMATIVE EXAMPLE 12
 Preparation of Amine-epoxide Adduct (66 Percent Capped)
 Into a one-liter reaction flask equipped with a stirrer, heating mantle,
 nitrogen line, cooling condenser, and thermometer was charged 485 grams
 (0.4 equivalents) Jeffamine 2000 (Texaco Chemical Company, Houston, Tex.)
 and 142.2 grams (0.61 equivalents) of polyepoxide of propoxylated (5PO)
 pentaerythritol (Henkel Corporation, Ambler, Pa.). The reaction mixture
 was heated slowly to 125.degree. C. to 130.degree. C. with stirring and
 held at this temperature for about 2.5 hours. The reaction mixture was
 then cooled to 70.degree. C. and analyzed for epoxide and amine content.
 The product amine polyepoxide adduct had 0.4 meq/gm of total amine and
 0.33 meq/gm of epoxide which indicated that about 66 percent of the
 initial free epoxide groups had been reacted with the amine.
 Preparation of Self-Dispersing Resin
 Into a 250 mL reaction flask equipped with heating mantle, nitrogen line,
 cooling condenser, thermometer and stirring means, was charged 66.4 grams
 (0.348 equivalents) of the diglycidyl ether of bis-phenol A, and 19.6
 grams (0.172 equivalents) of bis-phenol A. The reactants were heated to
 95.degree. C. and then 12.0 grams (0.004 equivalents) of the amine-epoxide
 adduct prepared above was added with 0.15 grams triphenyl phosphine. The
 reaction mixture was heated slowly to 150.degree. C. with stirring
 whereupon an exothermic reaction was observed, cooling was immediately
 applied to maintain the reaction temperature between 150.degree. C. and
 160.degree. C. After the exothermic reaction subsides, the reaction
 mixture was maintained at 160.degree. C. for an additional hour followed
 by a 15 minute period at 190.degree. C. The reaction mixture was then
 cooled to 160.degree. C. and 14 grams of propyl Cellosolve.TM. (trademark
 of Union Carbide Corporation) was added which immediately began refluxing.
 The reaction mixture was cooled to 100.degree. C. and analyzed. The
 resultant self-dispersing resin, present at 87.5 percent solids in propyl
 Cellosolve.TM., has 0.07 meq/gm total amine and an epoxide equivalent
 weight of 552 based on resin solids.
 Preparation of Water-Borne Dispersion
 Into a 500 mL reaction flask equipped with a stirrer, heating mantle,
 nitrogen line, cooling condenser and thermometer was charged 112 grams of
 the self-dispersing resin (SDR) prepared as above. The resin was heated to
 100.degree. C. whereupon 16.5 grams of water were added gradually with
 stirring over a thirty minute period while the temperature dropped to
 about 55.degree. C. Then an additional 48 grams of water was added as the
 temperature was brought to 70.degree. C. over twenty minutes. At
 70.degree. C., there was added 2 grams of water followed by stirring for
 twenty minutes and then 3 grams of water was added. The resulting water in
 oil dispersion was stirred for 45 minutes while it cooled to 45.degree.
 C., and thereafter was in the form of an oil in water dispersion. After
 the inversion was completed, 2.0 grams of C.sub.5-10 alcohol mono-glycidyl
 ether from CVC Specialty Chemicals Corp. was added as a reactive diluent.
 Then 36.3 grams of water was added at 50.degree. C. over a one hour
 period. The resulting water-borne dispersion contained 56 percent resin
 solids in water/propyl Cellosolve.TM. (82/18) solvent.
 Preparation of Coating Composition
 Into a 25 mL plastic cup was charged 12.4 gm (56 percent solids) of the
 water-borne dispersion prepared as above followed by an equal equivalent
 amount (2 gm) of epoxy curing agent available as 8290 by HiTech (a
 modified diethylene triamine with a hydrogen equivalent weight of 163).
 Sufficient water is then added to bring the mixture to a spreadable
 consistency. The epoxy dispersion/curing agent blend is aged for 10
 minutes then a film casting was produced by drawing the blend down on a
 pre-sanded TRU COLD cold rolled steel panel (3.times.6.times.0.32 inches)
 using a #34 wire wound steel rod. The film was tack-free after 45 minutes.
 The physical properties of the coating composition which were rated "PASS"
 were measured after the film had air-dried at room temperature for 28
 days.