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United States Patent Office Patented Mar 2,930,779 United States Patent Office Patented Mar. 29, 1960 2 carbonate is at least one nitrogenous compound selected 2,930,779 from the class consisting of ammonia and primary REACTION PRODUCTS OF A POLYMER OF A amines, the latter having only single bonds between any WNYLENE ESTER AND A NTROGENOUS adjacent carbon atoms of any straight-chain radical COMPOUND which is a component thereof. The present invention is separate and distinct from the invention disclosed and Erhart K. Drechsel, Springdale, Conn, assignor to Amer claimed in the aforementioned patent, as it involves the ican Cyanamid Company, New York, N.Y., a corpo use of a polymer of vinylene carbonate in preparing a ration of Maine different kind of synthetic material. No Drawing. Application May 3, 1954 O It is a primary object of the present invention to Serial No. 429,689 prepare a new class of synthetic materials, more particu larly resinous compositions, which have particular utility 8 Claims. (CI. 260-72) in the plastics and coating arts, e.g., as coating, laminating, adhesive, impregnating, casting and molding compositions This invention relates to the production of new syn 15 as well as in other applications, for instance, in the treat thetic materials and, more particularly, new resinous (or ment of textiles, paper, etc. They also may be used as potentially resinous) compositions which are especially components of plastics and coatings compositions. Other suitable for use in the plastics and coating arts. My new objects of the invention will be apparent to those skilled compositions are obtained by reaction between ingredients in the art as the description of the invention proceeds. comprising (1) a polymer (including both homopolymers 20 The present invention is based on my discovery that and copolymers or interpolymers) of an unsaturated new and valuable materials for use in coating, molding ester, more particularly an unsaturated carbonate, and and other applications can be prepared by effecting re specifically vinylene carbonate containing at least 10 mole action between ingredients comprising (1) a polymer of percent of combined vinylene carbonate) and (2) at least vinylene carbonate containing at least 10 mole percent one nitrogenous compound selected from the class con 25 of combined vinylene carbonate and up to 90 mole per sisting of ammonia, primary amines (including both the cent of a different compound which is copolymerizable primary monoamines and polyamines) and the secondary with vinylene carbonate and which contains a CH=C< amines (including both the secondary monoamines and grouping, and (2) at least one nitrogenous compound se polyamines). The scope of the invention also includes lected from the class consisting of (a) ammonia, (b) aldehyde-reaction products, specifically formaldehyde-re 30 primary amines and (c) secondary amines. Mixtures of action products, of the aforementioned reaction products any two or all three of the nitrogenous compounds of of a polymer of vinylene carbonate and the aforesaid (a), (b) and (c) in any proportions can be used, if de nitrogenous compound, as well as method features. In sired. The polymer of vinylene carbonate may be homo stead of an aldehyde as a reactant, other active carbonyl polymeric vinylene carbonate or it may be a copolymer containing compounds can be used, e.g., a ketone. 35 containing at least 10 mole percent of combined vinylene Illustrative examples of amines that can be used as a carbonate, e.g., one containing from 10 or 15 to 90 or reactant with the aforementioned polymer of vinylene 95 or even as high as 99.9 mole percent of combined carbonate are the alkanol monoamines, e.g., the ethanol ... vinylene carbonate. Advantageously, if a copolymer be monoamines, propanol monoamines, etc., containing at employed, it is one which is a product of polymerization least one hydrogen atom attached to the amino nitrogen 40 of a mixture of copolymerizable ingredients including atom; the hydrocarbon-substituted monoamines contain (a) vinylene carbonate and (b) a different compound . ing at least one hydrogen atom attached to the amino containing a CH2=CC grouping, more particularly a nitrogen atom, e.g., the primary and secondary, saturated single CH2=CC grouping (e.g., vinyl chloride, vinyl and unsaturated aliphatic (including cycloaliphatic) hy idene chloride, styrene, the various methyl-, ethyl- and drocarbon monoamines, the primary and secondary aro 45 other lower alkyl-styrenes, the various chlorostyrenes, matic hydrocarbon monoamines, the primary and second acrylonitrile, methacrylonitrile, acrylamide, methocryl ary, aromatic-substituted aliphatic hydrocarbon mono amide, etc.), the vinylene carbonate of (a) constituting amines, and the aliphatic-substituted aromatic hydrocar at least 50 mole percent, more particularly from 60 to bon monoamines; the polyalkylene polyamines contain 95 mole percent, of the said mixture of copolymerizable ing at least one amine grouping having at least one hy 50 ingredients. drogen atom attached to the amino nitrogen atom; and Vinylene carbonate has the formula others that will be apparent to those skilled in the art from the foregoing general examples and from the more H = H specific examples given hereinafter. Thus, it will be ap parent that there also can be used amines containing one ( C ) or more (e.g., two, three, four, five or higher number) 55 primary amino groups together with one or more (e.g., O two, three, four, five or higher number) secondary amino When ammonia or a primary saturated aliphatic mono groups, with or without hydroxyl or other active or in amine is employed as a reactant with a polymer of vinyl active groups (e.g., tertiary amino groups) attached to ene carbonate the initial reaction which takes place may the chain. Hydrazine and substituted hydrazines contain 60 be illustrated by the following equation, and for purpose . ing at least one hydrogen atom attached to an amino of specific illustration ammonia is shown as the nitro nitrogen atom also can be employed as the amine react genous compound employed: . ant with the polymer of vinylene carbonate. I – H-H- In my copending application Serial No. 400,107, filed 65 - H-E- December 23, 1953, now Patent No. 2,794,013, dated o, o --NH May 28, 1957, I have disclosed compositions compris C ing a reaction product of ingredients comprising vinylene O carbonate (monomeric vinylene carbonate) and am The reaction product of Equation II is capable of monia, or a primary or secondary amine, or a mixture 70 undergoing inter-reaction between molecules thereof to of such nitrogenous compounds. The claims of the afore form higher-molecular-weight polymers. Or, the reaction. s said patent specify that the reactant with the vinylene product of Equation II can be reacted with an active 3,980,779 3. 4. carbonyl-containing compound or compounds, for in the aforementioned vinylene carbonate polymers with stance an aldehyde, a ketone, a mixture of an aldehyde such polyamines may be illustrated by the following and a ketone in any proportions, etc., to form a new class equation where a polyamine represented by the formula of condensation products, more particularly resinous or HN-R-NH2, where R represents an alkylene radical, potentially resinous condensation products. When the 5 is taken as illustrative of the amine reactant: active carbonyl-containing compound is an aldehyde, specifically formaldehyde, the initial reaction between -GH-E- -CE-CH the aldehyde and the reaction product of Equation II O O o b can be illustrated by the following equation: N / -- N / --HN-R-NH-) O C C -C-C- I -CH-CH-b d b Cs-O O ar O --HCHO- EI on. Cs:0 / N NH 7. N --on CEOH. 5 H. H." The N-carbinol, specifically N-methylol, derivative ob O-C-N-R-N--0 tained by the above reaction is capable of further re action to form the corresponding N-methylene deriva -CH-CE9 tives and cross-linked resinous polymers, that is, poly 20 mers in a cured or substantially insoluble, substantially ÖH, J, infusible state. In preparing the reaction product ("vinylene car The choice of the active carbonyl-containing com bamate” polymer) of the vinylene carbonate polymer pound, which is used as a reactant with the reaction with the aforementioned nitrogenous compound (that is, product of the polymer of vinylene carbonate and the 25 ammonia or a primary or secondary amine) the propor aforesaid nitrogenous compound, is dependent largely tions of the reactants can be widely varied depending, upon economic considerations and the particular proper for example, upon the particular starting reactants ei11 ties desired in the finished product. I prefer to use as ployed and the particular conditions of reaction. The the active carbonyl-containing compound an aldehyde, amount of the nitrogenous compound should be sufficient and more particularly formaldehyde or compound en 80 to react with at least one of the vinylene carbonate units gendering formaldehyde, e.g., paraformaldehyde, hexa in the polymer molecule, more particularly from one to methylenetetramine, trioxane, etc. Illustrative examples all of the aforesaid vinylene carbonate units. Ordinarily of other aldehydes that may be employed are acetalde the nitrogenous compound is employed in an amount hyde, propionaldehyde, butyraldehyde, heptaldehyde, such that at least 1%, preferably at least 5% e.g., from octaldehyde, acrolein, methacrolein, crotonaldehyde, 35 10 or 15% up to 100%, of the vinylene carbonate units benzaldehyde, furfural, hydroxyaldehydes (e.g., aldol, are converted into the corresponding carbamate units. glucose, glycollic aldehyde, glyceraldehyde, etc.), mix The temperature of the reaction also can be varied tures thereof, or mixtures of formaldehyde (or compounds considerably depending, for instance, upon the particular engendering formaldehyde) with such aldehydes. Pilus reactants employed, the rapidity of the reaction wanted, trative examples of aldehyde-addition products that may 40 the particular properties desired in the reaction product, be used instead of the aldehydes themselves are the and other influencing factors.
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