N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and drilling fluids containing N-hydroxyalkylated polyamines are provided, in which the N-hydroxyalkylated polyamine includes Formula (I): ##STR00001##
where R.sup.1 and R.sup.2 are independently a C or CH group; R.sup.3 is an aliphatic hydrocarbyl; R.sup.4 and R.sup.5 are independently acyclic hydrocarbyls, or R.sup.1, R.sup.2, R.sup.4, and R.sup.5 are covalently connected to form a cyclic hydrocarbyl; and R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.

N-hydroxyalkylated polyamines, methods of making N-hydroxyalkylated polyamines, and drilling fluids containing N-hydroxyalkylated polyamines are provided, in which the N-hydroxyalkylated polyamine includes Formula (I): ##STR00001##
where R.sup.1 and R.sup.2 are independently a C or CH group; R.sup.3 is an aliphatic hydrocarbyl; R.sup.4 and R.sup.5 are independently acyclic hydrocarbyls, or R.sup.1, R.sup.2, R.sup.4, and R.sup.5 are covalently connected to form a cyclic hydrocarbyl; and R.sup.6, R.sup.7, R.sup.8, and R.sup.9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.

The present invention relates in part to novel cationic lipids and their use, e.g., in delivering nucleic acids to cells.

In a preferred embodiment, there is provided a process for separating an amine compound or a conjugate acid thereof and a carbamate compound or a conjugate acid thereof from a mixture having the amine compound, the carbamate compound, carbon dioxide and at least one anionic contaminant salt using an anionic exchange column, the process including passing the mixture through the column to obtain a first effluent and passing through the column an extraction fluid to obtain a second effluent, where the extraction fluid most preferably includes carbonic acid.

In a preferred embodiment, there is provided a process for separating an amine compound or a conjugate acid thereof and a carbamate compound or a conjugate acid thereof from a mixture having the amine compound, the carbamate compound, carbon dioxide and at least one anionic contaminant salt using an anionic exchange column, the process including passing the mixture through the column to obtain a first effluent and passing through the column an extraction fluid to obtain a second effluent, where the extraction fluid most preferably includes carbonic acid.

Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepared from racemic or stereochemically pure epoxides. Aminoalcohol lipidoids or salts forms thereof are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these aminoalcohol lipidoid compounds, they are particularly suited for the delivery of polynucleotides. Complexes, micelles, liposomes or particles containing the inventive lipidoids and polynucleotide have been prepared. The inventive lipidoids may also be used in preparing microparticles for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.

Aminoalcohol lipidoids are prepared by reacting an amine with an epoxide-terminated compound are described. Methods of preparing aminoalcohol lipidoids from commercially available starting materials are also provided. Aminoalcohol lipidoids may be prepared from racemic or stereochemically pure epoxides. Aminoalcohol lipidoids or salts forms thereof are preferably biodegradable and biocompatible and may be used in a variety of drug delivery systems. Given the amino moiety of these aminoalcohol lipidoid compounds, they are particularly suited for the delivery of polynucleotides. Complexes, micelles, liposomes or particles containing the inventive lipidoids and polynucleotide have been prepared. The inventive lipidoids may also be used in preparing microparticles for drug delivery. They are particularly useful in delivering labile agents given their ability to buffer the pH of their surroundings.

A process is provided for converting one or more cyclic ethylene ureas into corresponding ethylene amines and carbon dioxide. The process may include contacting water with one or more cyclic alkylene urea compounds comprising one or more cyclic alkylene urea moieties in a reaction vessel at a temperature of 150 to 400 C., optionally in the presence of an amine compound selected from the group of primary amines, cyclic secondary amines and bicyclic tertiary amines. The mole ratio of water to cyclic alkylene urea moieties is in the range of from about 0.1 to about 20. In the reaction, at least a portion of the cyclic alkylene urea moieties are converted to corresponding alkylenediamine moieties and carbon dioxide. The process may further include removing the carbon dioxide from the liquid reaction mixture in a stripping vessel by feeding a stripping fluid to the stripping vessel. Further, the process may include removing a carbon dioxide-containing stripping fluid.

A process is provided for converting one or more cyclic ethylene ureas into corresponding ethylene amines and carbon dioxide. The process may include contacting water with one or more cyclic alkylene urea compounds comprising one or more cyclic alkylene urea moieties in a reaction vessel at a temperature of 150 to 400 C., optionally in the presence of an amine compound selected from the group of primary amines, cyclic secondary amines and bicyclic tertiary amines. The mole ratio of water to cyclic alkylene urea moieties is in the range of from about 0.1 to about 20. In the reaction, at least a portion of the cyclic alkylene urea moieties are converted to corresponding alkylenediamine moieties and carbon dioxide. The process may further include removing the carbon dioxide from the liquid reaction mixture in a stripping vessel by feeding a stripping fluid to the stripping vessel. Further, the process may include removing a carbon dioxide-containing stripping fluid.

An integrated process for manufacturing polyethyleneamine compounds selected from the group of polyethyleneamines and hydroxyethylethyleneamines is provided. The process includes in an adduction step, providing a CO.sub.2 adduct of a starting compound comprising a NHCH.sub.2CH.sub.2NH moiety or a NHCH.sub.2CH.sub.2OH moiety, or HOCH.sub.2CH.sub.2OH, in a reaction step reacting a hydroxy-functional compound selected from the group of ethanolamines and dihydroxyethane with an amine-functional compound, wherein at least part of the total of hydroxy-functional compounds and amine-functional compounds is provided in the form of a CO.sub.2 adduct, to form CO.sub.2 adduct of a product polyethyleneamine compound, in an elimination step converting CO.sub.2 adduct of product polyethyleneamine compound to the corresponding product polyethylene amine compound, wherein a fraction comprising a recycle compound comprising a NHCH.sub.2CH.sub.2NH moiety or a NHCH.sub.2CH.sub.2OH moiety, or HOCH.sub.2CH.sub.2OH, or CO.sub.2 adducts thereof, is provided from the end of the reaction step or the elimination step to the adduction step or to the reaction step, wherein the recycle compound has per molecule on average fewer of the total of NHCH.sub.2CH.sub.2NH moieties and NHCH.sub.2CH.sub.2OH moieties than the product polyethyleneamine compound.