GB913350A - Process for the acylation of organic compounds - Google Patents

Abstract

Organic compounds which contain hydroxy or amino groups (primary or secondary) are acylated with an acyl-urethane containing at least one group of the general formula -CO-NH-CO-XR, wherein X represents oxygen or sulphur and R is a hydrocarbon group which may have an alkoxy or halogen substituent. This acylating agent is useful in bringing about cross-linking in compounds of high molecular weight, such as polyvinyl alcohol, cellulose, a polyglycol, a polyamine or a polyamide. In Example 2, N,N1-adipyl-bis-carbamic acid-isopropyl-ester is heated at 160 DEG C. with neopentyl glycol. The reaction-product, on cooling, is a resinous mass. In Example 3, the 2-amyl ester of N,N1-adipyl-bis-carbamic acid is heated with hexamethylene diamine. The solid product can be drawn out into filaments if the operation is carried out quickly. In Example 4, a solution of cellulose acetate in acetone is mixed with the 2-chlorophenyl ester of N,N1-oxalyl-bis-carbamic acid. The resulting mixture is cast into a film and heated above 130 DEG C. The resultant film is insoluble in acetone. In Example 8, films are obtained by reacting the acrylyl urethane. CH2=CH,CO,NH,CO,O,CH2,CH2,OCH 3 with polyvinyl alcohol. The Specification states that bis-acyl-urethanes may be reacted with the polyamides obtained by condensing an oxalic ester with a mixture of dipropylenetriamine and N-methyl-dipropylenetriamine.ALSO:The invention comprises a process for the acylation of organic compounds, which contain hydroxyl or primary or secondary amino groups, by reacting the given organic compound with a compound which contains at least one group of the general formula -CO-NH-CO-XR wherein X represents oxygen or sulphur, and R represents a hydrocarbon radical, which may have an alkoxy or halogen substituent. Typical examples of specified acylating agents may be prepared by reacting the acid chloride of isobutyric acid, diglycolic acid, isophthalic acid or trimesic acid with methyl carbamate, b -methoxyethyl carbamate, or 2-chlorophenyl carbamate. The acylating agents may also b prepared by reacting an acylisocyanate with an alcohol, mercaptan or phenol. In an example, 4-chlorobenzyl alcohol is heated to 165 DEG C. with N,N1-adipyl-bis-carbamic acid isopropyl ester in the presence of o-dichlorobenzene as solvent. Isopropanol is evolved; and N,N1-adipyl-bis-carbamic acid-4-chlorobenzyl ester crystallizes out on cooling. Mention is made to the S-methyl ester of N,N1-adipyl-bis-carbamic acid. The Specification also relates to the production and modification of synthetic polymers by reacting the acylating agents with neopenyl glycol, hexamethylene diamine, acetyl cellulose and polyvinyl alcohol (see Group IV(a)).