Imidazoline I This compound was prepared by reacting. The reactants were previously agitated throughout the reaction and two moles of water were lost. The product was a mixture of imidazolines having the following predominant structure:. The reaction conditions were the same as those used in preparing'imidaz-oline I.
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The product was a mixture of 'imidazolines in which the. The reaction was carried out under the same conditions used in preparing Empol is dimerized linoleic acid sold comimidazoline I. The product comprised a mixture of 'imidazolines in which the following structure predominated:. It was then heatedv in an open vessel. Initially, the viscosity. The reaction product was a. The effects of such heating periods are set forth in Table III. In the first batch, the epoxide had an oxirane oxy-. Each batch was heated for onehour at C.
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The reaction products were identical in themselves but had a lower viscosity than the prodnets of Example 3. In the first batch, parts of :imidazoline were mixed with parts of epoxy, and in the second batch 10 parts, of imidazolineq were admixed with parts of epoxy. The batches are designated 5a and 5b? A series of compositionswere madeiupin which the re- 1 action productsof Examples 1 to 5 were variously incorporated with polyvinyl chloride.
They are compared with formulations'in which such reaction products were not used The formulations and the results are set forth in the following tables:. A represents the unheated mixture. Imidazoline III. Color Light brown Dark brown Odor Mild Acrid Very slight oily Slight odor of octyl alcohol. Appearance Smooth, trans- Blistered, Smooth, clear. Smooth, clear.
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Soluble in cyclohexanone N No es. Adhesion to steel Good Percent extraction in luene 9n 1 In formulation B, the imidazoline and epoxide were not pre-reacted but were present as a physical mixture. Analysis of the data in Table II shows that formulation A is superior in such properties as odor, solubility, adheparts of. The effect of cure time andtemperaturc on adhesion and degree of crosslinking is straightforward. The longer the reaction is permitted to continue the more tightly bound the plasticizer becomes and the whole network is crosslinked to a greater-extent.
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The following represents a variety of formulations in which a mixture of Geon a coplymer consisting of vinylidene chloride s ion, making it ideal for use as a flowed-in, heat curable,. The compositions and results are tabulated as follows:.
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Viscosity at room temperature, centipoises , Viscosity at roomternperature after one year,-. The very low extraction values for r Flexlbfllty S formulation A are probably attributable to other factors Adhesion f j connected with the specific grade of epoxidized soybean gfi i o eoreimous lacquer mi oil vused rather than its oxirane content taken alone. A eslon to Pheno 1c lacquer Xce Color Red-brown. The results in Table V show that both the higher-and The properties, especially the viscosity stability, make lower ratios of epoxy to imidazoline II yield a plastisol' thls malenal all excellent adheslve Sealing Compound whose adhesion and oil resistance is greatly improved fiowed'm gaskets on enameled metal contamers- Insolu overaconventional plastisol based on the epoxyplasticizer a g: cyclohexanone indicates cured or crosslinked and polyvinyl chloride alone.
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Moreover, the higher p y EXAMPLE 7 1m1dazol1ne material givesvirtually no loss in In this example, 5 formulations were prepared, teach u consisting of 5 parts of imidazoline II and 10 parts of adheslve and Teslstant gasketmg matenal C an ;epoxystearate -lower ester. The; formulations are tainers. It also utility in the preparation of pri n identified by the parentheticalletter which'precedes the plates when oil-based inks are used.
Each then added to 20 pf of The resultlng p imid-azoline-ester mixture. Properties of the stable at room temperature. Viscosity stability at C Excellent ellent ent Fair Good. Cured minutes at 0. Percent extraction in toluene 20 Adhesion to epoxy lacquer Good Adhesion to oleoresinous lacquer Fair Adhesion to phenolic lacquer Good Adhesion to tin plate Po0r l Insolubility in cyclohexanone indicates cured or erosslinked polymer. It is also compared with a composition containing the same copolymer compounded with separate additions of a conventional plasticizer and an imidazoline in lieu of an imidazoline-epoxy compound reaction product.
The resulting solution was split into two equal portions of 50 grams each, designated as A and B, with each portion containing grams of copolymer. Into port-ion A, there were then separately added 1 gram of imidazoline IV and 3 grams of dioctyl phthalate. Both portions were then baked at C.
It is noted that in the absence of the epoxy compoundimidazoline reaction product in the composition, portion A blackened and degraded by the time it became insoluble crosslinked. On the other hand, portion B, which contained the reaction product, provided a safety factor of about 3 minutes between crosslinking and degradation. The same results are obtainable with extrusion grade resins. The properties of portion B render it useful as a protective coating for contact with organic solvents or corrosive environments.
Example 9 shows the use of a product obtained by reacting an imidazoline and an epoxide known commercially as Bpoxide The propenties of this composition were as follows:. Color Reddish tan.
Effect of cyclohexanone Some swelling. Adhesion to aluminum Excellent. Shore A hardness It is apparent that the described reaction product pro motes very rapid crosslinking without appreciable degradation and affords excellent adhesive p-ropenties While exhibiting viscosity stalbility at room temperature.
The resulting reaction product was a clear, viscous fluid which was stable at room temperature. Oxiron is a product of Food Machinery and Chemicals Company and is identified as epoxidized poly'butadiene. Properties of this composition were as follows:. Polyvinyl chloride is not readily dissolved by most organic solvents and is blended to various plasticizers with difficulty. The copolymer with vinyl acetate, for example, is much more compatible with plasticizer than straight polyvinyl chloride.
The proportions of the components in the final compositions may be varied over wide limits, depending upon the type of processing to be used, for example, extrusion, molding, calendering and the properties desired. In ad-' dition, various other materials may be added, such as colors and fillers. The ox irane oxygen content of the epoxidized ester is generally between about 3 and 7. A curable composition comprising 1 a polymeric.
Where R is a member selected from theclass consisting of hydrogemand an alkyl radical containingl to 6 carbon atoms, and n has one of the values O to 5. A polymer obtained by curing the composition of claim 1 by heating at atemperature'between. A curable composition according to claim 1 wherein the epoxy compound is selected from.
A composition according to claim 3 wherein the epoxy compound is an epoxystearate lower ester. A polymer: obtained by heating the composition of claim 3 for 1 to 10 minutes at C. Isaacs, Brookline, Mass. The most desirable imidazolines for this purpose preferably contain free primary amino groups and are represented by the following structure: In the above, R may be 1 An alkyl chain of 1 to 36 carbon atoms derived from a carboxylic acid; or 2 The group and homologues thereof where n is a number-from Otto 5, and R may be hydrogen or a hydrocarbon group such as methyl, ethyl, propyl, butyl, etc, and R?