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.

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.

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.

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.

The invention relates to a synthesis method for at least one nitrogen compound belonging to the family of partly N-hydroxyethylated tertiary 1,6-hexanediamines with general formula (I) as follows:

##STR00001##

wherein radicals R.sub.1, R.sub.2, R.sub.3 are each selected indiscriminately among a methyl radical and a hydroxyethyl radical, and at least one radical among R.sub.1, R.sub.2, R.sub.3 is a methyl radical,
comprising at least a first reaction between a first halogen atom-free precursor compound and a second halogen atom-free precursor compound.

The first precursor compound comprises a carbon skeleton consisting of a linear sequence of 6 carbon atoms with the 4 central carbon atoms bonded each to 2 hydrogen atoms and the carbon atoms in alpha and omega position not bonded to a halogen atom.

The invention relates to a synthesis method for at least one nitrogen compound belonging to the family of partly N-hydroxyethylated tertiary 1,6-hexanediamines with general formula (I) as follows:

##STR00001##

wherein radicals R.sub.1, R.sub.2, R.sub.3 are each selected indiscriminately among a methyl radical and a hydroxyethyl radical, and at least one radical among R.sub.1, R.sub.2, R.sub.3 is a methyl radical,
comprising at least a first reaction between a first halogen atom-free precursor compound and a second halogen atom-free precursor compound.

The first precursor compound comprises a carbon skeleton consisting of a linear sequence of 6 carbon atoms with the 4 central carbon atoms bonded each to 2 hydrogen atoms and the carbon atoms in alpha and omega position not bonded to a halogen atom.

The invention relates to a synthesis method for at least one nitrogen compound belonging to the family of partly N-hydroxyethylated tertiary 1,6-hexanediamines with general formula (I) as follows:

##STR00001##

wherein radicals R.sub.1, R.sub.2, R.sub.3 are each selected indiscriminately among a methyl radical and a hydroxyethyl radical, and at least one radical among R.sub.1, R.sub.2, R.sub.3 is a methyl radical,
comprising at least a first reaction between a first halogen atom-free precursor compound and a second halogen atom-free precursor compound.

The first precursor compound comprises a carbon skeleton consisting of a linear sequence of 6 carbon atoms with the 4 central carbon atoms bonded each to 2 hydrogen atoms and the carbon atoms in alpha and omega position not bonded to a halogen atom.