# US 5,349,011 A · Polyamide ester rheological additive, a solution containing the additive and thickened compositions containing the additive > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,349,011 A - Document ID: US5349011A - Status: Granted - Kind: A - Application number: 08/099,400 - Filed: 1993-07-30 - Granted: 1994-09-20 - Earliest claimed: 1991-08-16 - Assignees: Rheox, Inc. - Inventors: William W. Reichert; Murray C. Cooperman - Web page: https://patentgrep.com/patent/US5349011A ## CPC - C08G 69/44: Polyester-amides - C08G 69/28: Preparatory processes - C08G 69/34: using polymerised unsaturated fatty acids - C09D 7/43: Thickening agents - C08L 77/12: Polyester-amides - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A polyamide (or oligomeric amide) ester rheological additive especially for organic solvent-based compositions comprises the reaction product of a defined polycarboxylic acid, a diamine, an alkoxylated polyol and a capping agent. The additive exhibits excellent efficiency and ease of dispersibility and is especially effective when first predispersed in an organic solvent. Organic solvent-based compositions which may be thickened by using the rheological additive are aliphatic, aromatic, and some moderately polar solvent-based compositions. ## Claims ### Claim 1 A rheological additive comprising the reaction product of: a) polycarboxylic acid having at least 5 carbon atoms per acid group b) a first active hydrogen compound having the formula X.sub.m --R--Y.sub.n, wherein R represents a group containing from 2 to 12 carbon atoms, X and Y are groups independently selected from primary amino, secondary amino and hydroxyl, m and n are at least 1 and the sum of (m+n) is at least 2 and at least 90% of the X and Y groups participating in the reaction being primary amino, secondary amino and a mixture thereof; c) a second active hydrogen compound containing two active hydrogen functionalities wherein the hydrogen compound is represented by one of the following formulas: H--(OCH.sub.2 CH.sub.2).sub.n --OH wherein n=8-50 or ##STR4## wherein q+r=2-50, R.sub.1 is a long chain alkyl group C.sub.12 -C.sub.22, s is zero or one, and R is one of hydrogen, methyl and ethyl; and (d) capping agent. ### Claim 2 (depends on 1) The rheological additive according to claim 1, wherein the second active hydrogen compound is a polyether moiety with at least two active hydrogen groups. ### Claim 3 (depends on 1) The rheological additive according to claim 1, wherein the second hydrogen compound has at least one of an active amine or hydroxyl moiety at each termini of a polyether chain. ### Claim 4 (depends on 1) The rheological additive according to claim 1, wherein the polycarboxylic acid is selected from the group consisting of oligomers of fatty acids substantially comprised of dimerized fatty acid, sebacic acid, poly (butadiene) dioic acids, dodecane dicarboxylic acid and mixtures thereof. ### Claim 5 (depends on 1) The rheological additive according to claim 1, wherein at least 50% of the x+y groups in the first active hydrogen compound participating in the reaction are one of primary amino, secondary amino and a mixture thereof. ### Claim 6 (depends on 1) The rheological additive according to claim 1, wherein the first active hydrogen compound having the formula X.sub.m --R--Y.sub.n is selected from the group consisting of polyamines including 1,2-diaminoethane, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, 1,8-diaminooctance, 1,12-diaminododecane, 3,3-diaminopropyl-N-methyl-amino, N-alkyl-1,3-diaminopropanes where the alkyl group is a long carbon chain such as coco or tallow alkyl, soya alkyl, hydrogenated tallow alkyl, oleyl, stearyl and mixtures thereof, and amino alcohols, including ethanolamine, 6-aminohexanol, aminoethylethanolamine and mixtures thereof. ### Claim 7 (depends on 1) The rheological additive according to claim 1, wherein the reaction product is a reaction product of oligomer of fatty acid having a carbon chain of from 15 to 18 carbon atoms, diamine having from 6 to 12 carbon atoms, an ethoxylated C.sub.12 -C.sub.18 alkyl amine having 2 to 10 ethoxylated units, and monocarboxylic acid having from 8 to 22 carbon atoms as the capping agent. ### Claim 8 (depends on 1) The rheological additive according to claim 1, wherein, to form the reaction product, the amount of the first active hydrogen compound reacted is from about 0.75 to about 1.175 moles per mole of the reacted polycarboxylic acid, the amount of the second active hydrogen compound is from about 0.25 to about 0.50 mole per mole of the reacted polycarboxylic acid, and the amount of the capping agent is from about 0.3 to about 2.0 moles per mole of the reacted polycarboxylic acid. ### Claim 9 A pre-dispersed mixture of a rheological additive in an organic solvent, said rheological additive comprising the reaction product of: a) polycarboxylic acid having at least 5 carbon atoms per acid group; b) a first active hydrogen compound having the formula X.sub.m --R--Y.sub.n, wherein R represents a group containing from 2 to 12 carbon atoms, X and Y are groups independently selected from primary amino, secondary amino and hydroxyl, m and n are at least 1 and the sum of (m+n) is at least 2 and at least 90% of the X and Y groups participating in the reaction being primary amino, secondary amino and a mixture thereof; c) a second active hydrogen compound containing two active hydrogen functionalities wherein the hydrogen compound is represented by one of the following formulas: H--(OCH.sub.2 CH.sub.2).sub.n --OH wherein n=8-50 or; ##STR5## wherein q+r=2-50, R.sub.1 is a long chain alkyl group C.sub.12 -C.sub.22, is zero or one, and R is one of hydrogen, methyl and ethyl, and d) capping agent. ### Claim 10 (depends on 9) The pre-dispersed mixture according to claim 9, wherein the reaction product is a reaction product of oligomer of fatty acid having a carbon chain of from 16 to 18 carbon atoms, diamine having from 6 to 12 carbon atoms, an ethoxylated C.sub.12 -C.sub.18 alkyl amine having 2 to 10 ethoxylated units, and monocarboxylic acid having from 8 to 22 carbon atoms as the capping agent. ### Claim 11 A thickened organic composition containing the rheological additive in an amount sufficient to prevent formation of large agglomerates as may develop during storage, said rheological additive comprising the reaction product of: a) polycarboxylic acid having at least 5 carbon atoms per acid group b) a first active hydrogen compound having the formula X.sub.m --R--Y.sub.a, wherein R represents a group containing from 2 to 12 carbon atoms, X and Y are groups independently selected from primary amino, secondary amino and hydroxyl, m and n are at least 1 and the sum of (m+n) is at least 2; c) a second active hydrogen compound containing two active hydrogen functionalities wherein the hydrogen compound is represented by one of the following formulas: H--(OCH.sub.2 CH.sub.2).sub.n OH wherein n=8-50 or ##STR6## wherein q+r=2-50, R.sub.2 is a long chain alkyl group C.sub.12 -C.sub.22, s is zero or one, and R is one of hydrogen, methyl and ethyl, and (d) capping agent. ### Claim 12 (depends on 1) The thickened organic composition according to claim 1, wherein the reaction product is a reaction product of oligomer of fatty acid having a carbon chain of from 16 to 18 carbon atoms, diamine having from 6 to 12 carbon atoms, and ethoxylated C.sub.12 -C.sub.18 alkyl amine having 2 to 10 ethoxylated units, and monocarboxylic acid having from 8 to 22 carbon atoms as the capping agent. ### Claim 13 (depends on 1) The rheological additive according to claim 1, wherein the active hydrogen compound has no more than 12 carbon atoms and the alkoxylated active hydrogen compound has greater than 12 carbon atoms. ### Claim 14 (depends on 1) The rheological additive according to claim 1, wherein less than 90% of the X and Y groups participating in the reaction being primary amino, secondary amino and a mixture thereof.