Hydantoin epoxy

Figure 1. Infrared spectra for a toluene diisocyanate modified hydantoin epoxy/2-ethyl-l,3-hexanediol oligomer showing the OH and NH bands of the oligomer as a function of temperature in uncatalyzed and catalyzed formulations.

The Effect of Alkyl Substituents on the Properties of Cured Hydantoin Epoxy Resins... 

Epoxy resins based on glycidylation of bisphenols, cresol and phenol novolacs, polycarboxylic acids, polyols, amines, and aminophenols have been long known. Epoxidized linear and cyclic olefins have also been used as specialty epoxy resins. More recently, glycidylated heterocycles have been introduced, initially as specialty resins promising improved resistance to weathering. One heterocycle in particular, the hydantoin ring, has become of particular interest as an epoxy substrate (J ). 

In this paper we report on a series of hydantoin resins derived from a somewhat broader choice of aldehydes and ketones, and show how the 5-position substituents interact with several variants of common epoxy curing systems to produce the properties of the final cured systems. 

The simplest class of hydantoin epoxy resins are the 1,3-diglycidylhydantoins of Formula II. They were readily prepared from the 5,5-dialkyl or 5-monoalkylhydantoins and epichlorohydrin. The hydantoins (Formula l) were prepared from ketones or aldehydes via the Bucherer reaction. 

Table I lists typical properties of a baker s dozen of these resins, produced by typical direct preparations, without extensive purification. Overall, the viscosities of these resins were quite low, particularly by comparison to the well known general purpose epoxy resins based on the diglycidyl ether of bisphenol A (DGEBA). The more shielded higher alkylsubstituted hydantoin rings favored lower viscosities. Some anomalies in these viscosities presumably reflected either a tendency of certain resins to crystallize, or the presence of some species of higher molecular weight, formed by reaction of the glycidyl group with a second hydantoin ring.

In some instances a much purer diglycidylhydantoin species has been isolated. Pure Resin Ila, 1,3-diglycidyl-5,5-dimethyl-hydantoin, was a readily crystallizable solid, m. 72-73 C ( ), epoxy content 8.25 eq/kg. The less pure sample described in Table I tended to supercool for a limited time, and could then be handled as a liquid. A distilled grade of Resin Ilb,... 

ROOM TEMPERATURE CURED HYDANTOIN EPOXY RESINS... 

CATSIFF ET AL. Cured Hydantoin Epoxy Resins TABLE V... 

SOLVENT RESISTANCE OF AROMATIC AMINE-CURED HYDANTOIN EPOXY RESIN... 

Hydantoin epoxy resins having glycidyl groups in the 1- and 3-positions and one or two alkyl groups in the 5-position were prepared by the Bucherer reaction, followed by treatment with epichlorohydrin. These resins were crosslinked with hexahydrophthalic anhydride to examine the effect of alkyl substituents on the glass transition temperatures of the cured systems. 

Higher alkyl substituents shielded the hydantoin rings and gave lower glass temperatures. The same shielding effect was observed in the reduced hydrophilicity of higher alkyl-substituted hydantoin epoxy resins cured with triethylenetetramine. 

Hydantoins, thiohydantoins, and their substituted products are particularly useful as catalysts and as stabilizer agents in polymer chemistry and also in the preparation of epoxy resins.356,357 Thus hydantoins 148 are readily hardened, giving suitable polymers for the preparation of molding and lacquers. 

Dantocol . [Lonza] Dimethyl hydantoin glycols intermediates for epoxies, urethane resins, and antistatic lubricants for the textile and plastic industries. 

Bis(2-hydroxyethyl)-5,5-dimethyl-2,4-imidazolidinedione Dantocol DHE DEDM Hydantoin Di-(2-hydroxyethyl)-5,5-dimethyl hydantoin 1,3-Di-(hydroxyethyl)-5,5-dimethylhydantoin Diethylol dimethyl hydantoin EINECS 248 52-5 2,4-lmidazolidinedione, 1,3-bis(2-hydroxyethyl)-5,5-dimethyl-. Resin crasslinker in coatings and polymers intermediate for epoxies, urethane resins, and antistatic lubricants for the textile and plastics industries. Crystals mp = 63° pH 6.5 (5%). Lonzagroup. 

Com (Zea mays) starch Dextrin Diethyl toluene diamine Dilinoleic acid Dimethicone Dimethylaminoethyl acrylate Dimethylaminomethyl phenol Dimethyl hydantoin-formaldehyde polymer Dimethyl terephthalate Dioctyl maleate Dioctyl phosphite Diurethane dimethacrylate Elemi gum Epoxy, bisphenol A Epoxy, bisphenol F... 

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