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.

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

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 —NH—CH.sub.2—CH.sub.2—NH— moiety or a —NH—CH.sub.2—CH.sub.2—OH moiety, or HO—CH.sub.2—CH.sub.2—OH, 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 —NH—CH.sub.2—CH.sub.2—NH— moiety or a —NH—CH.sub.2—CH.sub.2—OH moiety, or HO—CH.sub.2—CH.sub.2—OH, 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 —NH—CH.sub.2—CH.sub.2—NH— moieties and —NH—CH.sub.2—CH.sub.2—OH moieties than the product polyethyleneamine compound.

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 —NH—CH.sub.2—CH.sub.2—NH— moiety or a —NH—CH.sub.2—CH.sub.2—OH moiety, or HO—CH.sub.2—CH.sub.2—OH, 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 —NH—CH.sub.2—CH.sub.2—NH— moiety or a —NH—CH.sub.2—CH.sub.2—OH moiety, or HO—CH.sub.2—CH.sub.2—OH, 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 —NH—CH.sub.2—CH.sub.2—NH— moieties and —NH—CH.sub.2—CH.sub.2—OH moieties than the product polyethyleneamine compound.

Methods of making N-hydroxyalkylated polyamines are provided, in which the method includes reacting a polyamine comprising Formula (XXIV): ##STR00001##
with a cyclic oxide to produce the N-hydroxyalkylated polyamine, where R.sup.1 and R.sup.2 are independently a —C or —CH group; R.sup.3 is an aliphatic hydrocarbyl; and R.sup.4 and R.sup.5 are independently acyclic hydrocarbyls, or are covalently connected to form an unsaturated cyclic hydrocarbyl.

Methods of making N-hydroxyalkylated polyamines are provided, in which the method includes reacting a polyamine comprising Formula (XXIV): ##STR00001##
with a cyclic oxide to produce the N-hydroxyalkylated polyamine, where R.sup.1 and R.sup.2 are independently a —C or —CH group; R.sup.3 is an aliphatic hydrocarbyl; and R.sup.4 and R.sup.5 are independently acyclic hydrocarbyls, or are covalently connected to form an unsaturated cyclic hydrocarbyl.

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.

The invention relates to an absorbent solution and to a method using this solution for removing acid compounds contained in a gaseous effluent, comprising water and at least one diamine 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.

The invention relates to an absorbent solution and to a method using this solution for removing acid compounds contained in a gaseous effluent, comprising water and at least one diamine 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.