Hydroxypolyamide gel forming agents

Abstract

Hydroxypolyamides, hydroxypolyamide products, and post-hydroxypolyamides are disclosed as gel forming agents. Hydroxypolyamides and post-hydroxypolyamides are prepared from known methods. Hydroxypolyamide products are produced from a modified polymerization procedure which utilizes strong base for deprotonation of ammonium salts from the esterification of stoichiometrically equivalent polyacid:polyamine salts. The hydroxypolyamide products are capable of gel formation at lower concentrations than hydroxypolyamides and post-hydroxypolyamides from the known methods of preparation, and are therefore superior gel forming agents.

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         8 . A process for making a hydroxypolyamide product comprising a hydroxypolyamide component and a salt component, each component produced in the same polymerization process, the hydroxypolyamide component being derived from at least one organic polyacid and at least one polyamine, wherein at least one organic polyacid and/or one polyamine bears at least one pendant hydroxyl group, the process comprising the steps of:
 a) forming a stoichiometrically molar balanced (1:1) salt from an organic polyacid and polyamine;   b) esterifying the carboxylate portion of one or more organic polyacid:polyamine salts in an alcohol with an acid source and converting the polyamine portion to a polyamine salt of the acid source; and   c) treating the esterified organic polyacid:polyamine salt in a solvent with base, wherein the base is stronger than a tertiary amine, to form a hydroxypolyamide product.   
     
     
         9 . A process in accordance with  claim 8 , wherein said the hydroxypolyamide component is derived from at least one organic polyacid selected from the group consisting of: aliphatic polyacids, carbocyclic polyacids, heterocyclic polyacids, arylalkyl polyacids; said polyacids with at least one substituent selected from group consisting of alkyl, alkenyl, and alkynyl groups, substituted alkyl, alkenyl, and alkynyl groups, aryl groups and/or substituted aryl groups, other groups, atoms other than hydrogen; said polyacids with at least one hetero atom in place of at least one carbon atom; said polyacids substituted with at least one pendant group selected from group consisting of alcohol, ester, ether, ketone, thiol, thioether, nitro, nitrile, and cyano groups. 
     
     
         10 . A process in accordance with  claim 8 , wherein said the hydroxypolyamide component is derived from at least one organic polyacid selected from the group consisting of: tartronic acid; tartaric acids; xylaric acid; arabinaric acids; ribaric acid; lyxaric acids; glucaric acids; mannaric acids; galactaric acid; idaric acids; and citric acid. 
     
     
         11 . A process in accordance with  claim 8 , wherein said the hydroxypolyamide component is derived from at least one polyamine selected from the group consisting of: alkylenepolyamines; alkenylenepolyamines; alkynylenepolyamines; alkylarylpolyamines; alkenylarylpolyamines; alkynylarylpolyamines; carbocyclic polyamines; heterocycylic polyamines; said polyamines substituted with at least one alkyl, alkenyl, and alkynyl groups, substituted alkyl, alkenyl, and alkynyl groups, aryl groups and substituted aryl groups, other groups, atoms other than hydrogen; said polyamines with at least one hetero atom in place of at least one carbon atom; said polyamines substituted with at least one pendant group selected from group consisting of alcohol, ester, ether, ketone, thiol, thioether, nitro, nitrile, cyano, and other common groups. 
     
     
         12 . A process in accordance with  claim 8 , wherein said the hydroxypolyamide component is derived from at least one polyamine selected from the group consisting of: ethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, decamethylenediamine, dodecamethylenediamine, 2-methylpentamethylenediamine, 4′-aza-4′-methylheptamethylenediamine, 3′,6′-dioxaoctamethylenediamine, L-lysine, and tris(2-aminoethyl)amine. 
     
     
         13 . A process in accordance with  claim 8  wherein said alcohol is selected from the group consisting of methanol, ethanol, 2-propanol, 1-propanol, t-butyl alcohol, 1-butanol, and 1-hexanol. 
     
     
         14 . A process in accordance with  claim 8  wherein said acid source is a mineral acid selected from the group consisting of hydrochloric acid, hydrobromic acid, hydrofluoric acid, phosphoric acid, and sulfuric acid. 
     
     
         15 . A process in accordance with  claim 8  wherein said solvent is selected from the group consisting of methanol, ethanol, 2-propanol, 1-propanol, 1-butanol, t-butyl alcohol, sec-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 1-hexanol, 2-hexanol, 3-hexanol, ethylene glycol, glycerol, dimethoxyethane, diglyme, dimethylformamide, acetonitrile, N-methylpyrrolidone, and dimethyl sulfoxide. 
     
     
         16 . A process in accordance with  claim 8  wherein said base stronger than a tertiary amine is a metal alkoxide comprising:
 a) a metal cation selected from the group consisting of sodium, potassium, lithium, calcium, and magnesium; and 
 b) an alkoxide derived from an alcohol selected from the group consisting of methanol, ethanol, 2-propanol, 1-propanol, t-butyl alcohol, 1-butanol, and 1-hexanol. 
 
     
     
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         37 . A method of making a gel comprising the steps of mixing at least one hydroxypolyamide, hydroxypolyamide product, or post-hydroxypolyamide and at least one liquid, wherein the hydroxypolyamide, hydroxypolyamide product, or post-hydroxypolyamide is derived from at least one organic polyacid and at least one polyamine, wherein at least one organic polyacid and/or polyamine bears at least one pendant hydroxyl group.