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United States Patent Office May 28, 1957 United States Patent Office May2,794,013 28, 1957 2 resinous compositions, which have particular utility in the plastics and coatings arts, e.g., as coating, laminating, 2,794,013 adhesive, impregnating, casting and molding compositions REACTION PRODUCTS OF VINYLENE CARBON as well as in other applications, for instance, in the treat 5 ment of textiles, paper, etc. They also may be used as ATE AND AM MONIA OR PRIMARY AMENE components of plastics and coatings compositions. Other Erhart K. Drechsei, Springdale, Conn., assignor to Amer objects of the invention will be apparent to those skilled icaia (Cyanaanid Company, New York, N. Y., a corpo in the art as the description of the invention proceeds. ration of Maigae The present invention is based on my discovery that new No Drawing. Application December 23, i953, and valuable materials for use in coating, molding and Serial No. 400,07 other applications can be prepared by effecting reaction between ingredients comprising vinylene carbonate and 12 Claims. (C. 260-77.5) at least one nitrogenous compound selected from the class consisting of (1) ammonia, (2) primary amines and This invention relates to the production of new syn 15 (3) secondary amines. Mixtures of any two or all three thetic materials and, more particularly, new resinous (or of the nitrogenous compounds of (1), (2) and (3) in any potentially resinous) compositions which are especially proportions can be used, if desired. When ammonia or suitable for use in the plastics and coating arts, and which a primary saturated aliphatic monoamine is employed as are obtained by reaction between an unsaturated ester, a reactant with vinylene carbonate the initial reaction specifically a vinylene ester, and a particular kind of 20 which takes place may be illustrated by the following nitrogenous compound. Still more particularly the in equation and for purpose of specific illustration ammonia vention is concerned with compositions comprising the is shown as the nitrogenous compound employed: product of reaction of ingredients comprising vinylene II carbonate and at least one nitrogenous compound select ed from the class consisting of ammonia, primary amines 25 H = H O O. --Nils --> (including both the primary monoamines and polyamines) N / and the secondary amines (including both the secondary C monoamines and polyamines). The scope of the inven O tion also includes method features. BIO H O O O Illustrative examples of amines that can be used as a 30 N | reactant with vinylene carbonate are the alkanol mono C-C-O-C-NE, mid C-C-O-C-NBI amines, e. g., the ethanol monoamines, propanol mono H amines, etc., containing at least one hydrogen atom at enol form tached to the amino nitrogen atom; the hydrocarbon-sub The reaction product of Equation II is capable of under stituted monoamines containing at least one hydrogen 3 5 atom attached to the amino nitrogen atom, e.g., the pri going interreaction between molecules thereof as illus mary and secondary, saturated aliphatic (including cyclo trated by Equation III below: - aliphatic) hydrocarbon monoamines, the primary and sec III O ondary aromatic hydrocarbon monoamines, the primary and secondary, aromatic-substituted aliphatic hydrocar 40 2. 2-CH-O-(-NH, -d bon monoamines, and the aliphatic-substituted aromatic E. O OH O. hydrocarbon monoamines; the polyalkylene polyamines. containing at least one amine grouping having at least (-CH-O--N-(-CH-O- -NH one hydrogen atom attached to the amino nitrogen atom; E. L. H. H. J. and others that will be apparent to those skilled in the For the reasons indicated in the foregoing equations it is art from the foregoing general examples and from the difficult to isolate a pure monomeric substance directly. more specific examples given hereinafter. Thus, it will As has been mentioned hereinbefore, vinylene car be apparent that there also can be used amines contain bonate also reacts with secondary amines. Taking a di ing one or more (e. g., two, three, four, five or higher 30 alkyl amine as illustrative of the secondary amine, the number) primary amino groups together with one or more initial reaction may be illustrated by the following equa (e.g., two, three, four, five or higher number) secondary tion: amino groups, with or without hydroxyl or other active or inactive groups (e.g., tertiary amino groups) attached IV to the chain. Hydrazine and substituted hydrazines con IC=eCB alkyl O O alkyl taining at least one hydrogen atom attached to an amino () / I | M. nitrogen atom also can be employed as the amine reactant o / -- HN -ms o–CH-O-C-N with vinylene carbonate. alkyl E. alkyl Vinylene carbonate, which is a cyclic carbonate of an O enediol, has the following formula: The complete reaction between the secondary amine and I HC-eCE the vinylene carbonate may not be as simple as Equation () ) IV might imply, since products other than the pure alde hyde generally are obtained. It is possible that the alde Nc^ hyde, which initially forms, reacts preferentially with ad O ditional amine reactant. Pure vinylene carbonate is a colorless liquid, M. P. 22 C. In addition to ammonia and the monoamines indicated and B. P. 162° C. at 735 mm. It can be prepared, for in the foregoing equations, vinylene carbonate also re example, by the dehydrochlorination of monochloroethyl acts with polyamines containing at least one hydrogen ene carbonate as described by Newman et al. in J. A. C. S., atom attached to an amino nitrogen atom. The reac vol. 75, pp. 1263-4 (March 5, 1953). tion of vinylene carbonate with such polyamines may be It is a primary object of the present invention to pre illustrated by the following equation wherein a polyamine pare a new class of synthetic materials, more particularly represented by the formula H2N-R-NH2, where R rep 2,794,018 resents an alkylene radical, is taken as illustrative of the various liquid alcohol-ethers, for example, ethylene glycol amine reactant: monomethyl ether, ethylene glycol monoethyl ether, di ethylene glycol monomethyl ether, diethylene glycol mono w ethyl ether, etc.; as well as numerous others that will be H-H 5 apparent to those skilled in the art. An excess of the 2 O () -- HN-R-NH -- amine reactant over stoichiometrical proportions may Y/ . constitute the medium in which the reaction is effected. The inert or active liquid medium or additive, if em ployed, can be used in any suitable amount ranging, for O 10 instance, from 0.1 to 40 or 50 times that of the weight (-oil-o--NE-R-NH-C-O-CH-5 - condensates of the primary reactants (vinylene carbonate and amine H^ Yi in reactive proportions). Good results have been ob tained when the liquid reaction medium was employed The type of reaction indicated in Equation V represents in an amount such that the primary reactants constituted an unique case whereby an unsaturated monomer (fully 15 from about 20% to about 30 or 35% by weight of the capable of addition or free radical polymerization) under- reaction mass. At the end of the reaction period, the goes polymerization in a condensation sense or fashion, inert or unreacted liquid medium is then removed from without attendant elimination of some simple molecule, the reaction mass by any suitable means, for example by e.g., water, ammonia, sodium chloride, etc. distillation, decantation, etc., or the solid reaction product As indicated hereinbefore, vinylene carbonate also 20 can be separated from the liquid component of the reac reacts with primary and secondary aromatic amines. With tion mass by filtration, centrifuging, etc. such amines an additional possibility for condensation pre- In order that those skilled in the art better may under sents itself in that the intermediate aldehyde may react stand how the present invention can be carried into effect, with the reactive nuclear hydrogen. Taking aniline as the following examples are given by way of illustration illustrative of the aromatic amine reactant, the reaction 25 and not by way of limitation. All parts and percentages may be illustrated by the following equation: are by weight. W HC=CH O () N/ ) +H:N-{ X - / (-CH-O-(-NH mme C B O O YC-C--O-C-N -cro-sn-(D-TorloTL (-oil-o--NH-O. -) cross-linked polymers The initial reaction products of this invention are gen- Example 1 erally soluble in water, or in other solvents, but become insoluble upon further advancement of polymerization, 40 that is, become substantially cured. Many of the Syn- Parts olar thetic compositions of this invention, as initially pre- Ratioi pared, are thermosetting (or potentially thermosetting) via 86.0 in nature and can be cured under heat in the form of Aqueous ammonia (approx. 29% NH3).---- 58.6 1. films or moldings without the aid of a curing catalyst. The proportions of the reactants can be widely varied 45 depending, for example, upon the particular starting react The aqueous ammonia is added to the vinylene car ants employed and the conditions of the reaction. In bonate at room temperature (25 C.). The reaction is general, approximately equal molar proportions are en extremely vigorous, the temperature rapidly rising to 45° ployed when ammonia or a primary or secondary mono C. The reaction mass is maintained below 50° C. by amine is the nitrogenous compound employed. With 50 external cooling. The lemon color which develops almost both the primary and secondary monoamines and the immediately persists throughout the reaction and is not polyamines the proportions of the amine are such that at extracted by either benzene or hexane. The viscous, oily least one primary or secondary amine group is present reaction product that is obtained may be used as a com therein for each mole of vinylene carbonate employed.
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