# US 9,040,064 B2 · Low-odor dimethicone copolyol sulfosuccinate surfactant compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,064 B2 - Document ID: US9040064B2 - Status: Granted - Kind: B2 - Application number: 12/454,646 - Filed: 2009-05-21 - Published: 2009-09-17 - Granted: 2015-05-26 - Earliest claimed: 2006-03-10 - Assignees: Rhodia Operations - Applicants: Richard J. Otterson; Kenneth E. Visek - Inventors: Richard J. Otterson; Kenneth E. Visek - Web page: https://patentgrep.com/patent/US9040064B2 ## CPC - A61K 8/899: containing sulfur, e.g. sodium PG-propyldimethicone thiosulfate copolyol - A61Q 19/00: Preparations for care of the skin - C08G 77/392: containing sulfur - C08G 77/46: containing polyether sequences - C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Dimethicone copolyol sulfosuccinate surfactant compounds having low-odor characteriztics are disclosed. The low-odor dimethicone copolyol sulfosuccinate is substantially free from propionaldehyde and acid-releasable precursors of propionaldehyde, thereby substantially eliminating the cosmetically undesirable odor characteriztic of conventional dimethicone copolyol sulfosuccinate surfactants. The low-odor dimethicone copolyol sulfosuccinates are suitable for use as surfactants in household or personal care products and applications. ## Claims ### Claim 1 A low-odor composition that is substantially free from propionaldehyde and acid-releasable precursors of propionaldehyde and suitable for use in cosmetic and personal care applications, the composition comprising a dimethicone copolyol sulfosuccinate produced by the steps of: reacting a dimethicone copolyol with maleic anhydride to form a maleic monoester, the dimethicone copolyol being substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; and sulfonating the maleic monoester with a compound selected from the group consisting of an alkali metal sulfite, an alkaline earth sulfite, ammonium sulfite, an amino sulfite, and a combination of any of the foregoing with an amino alcohol. ### Claim 2 (depends on 1) The composition of claim 1 wherein the dimethicone copolyol has an equivalent weight in the range of about 350 to about 1100 grams per equivalent. ### Claim 3 (depends on 2) The composition of claim 2 wherein the dimethicone copolyol has a calculated HLB value in the range of about 10 to about 17. ### Claim 4 (depends on 1) The composition of claim 1 wherein the composition contains less than 3200 parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde, and is free of objectionable odor sensorially discernible to a human observer compared to that of a counterpart composition containing greater than 3200 parts of parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde. ### Claim 5 (depends on 1) The composition of claim 1 wherein the dimethicone copolyol sulfosuccinate has the formula: wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M+ is an alkali metal cation or ammonium group; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100. ### Claim 6 (depends on 5) The composition of claim 5 wherein R is selected from the group consisting of: —(C2H4O)s—C2H4—; —(C3H6O)t—C3H6—; and —(C2H4O)v—(C3H6O)w—Y—; wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C2H4 or C3H6. ### Claim 7 (depends on 5) The composition of claim 5 wherein the composition contains less than 3200 parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde, and is free of objectionable odor sensorially discernible to a human observer compared to that of a counterpart composition containing greater than 3200 parts of parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde. ### Claim 8 (depends on 1) The composition of claim 1 wherein the dimethicone copolyol sulfosuccinate has the formula: wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M′(+2) is an alkaline earth metal cation; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100. ### Claim 9 (depends on 8) The composition of claim 8 wherein R is selected from the group consisting of: —(C2H4O)s—C2H4—; —(C3H6O)t—C3H6—; and —(C2H4O)v—(C3H6O)w—Y—; wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C2H4 or C3H6. ### Claim 10 (depends on 8) The composition of claim 8 wherein the composition contains less than 3200 parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde, and is free of objectionable odor sensorially discernible to a human observer compared to that of a counterpart composition containing greater than 3200 parts of parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde. ### Claim 11 (depends on 1) The composition of claim 1 wherein the dimethicone copolyol sulfosuccinate has the formula: wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; X+ is an ammonium group derived from an amino alcohol, an amine ethoxylate or an amine propoxylate; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M+ is an alkali metal cation or ammonium group; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100. ### Claim 12 (depends on 11) The composition of claim 11 wherein the ammonium group, X+, is derived from at least one amine selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine and diglycolamine. ### Claim 13 (depends on 11) The composition of claim 11 wherein R is selected from the group consisting of: —(C2H4O)s—C2H4—; —(C3H6O)t—C3H6—; and —(C2H4O)v—(C3H6O)w—Y—; wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C2H4 or C3H6. ### Claim 14 (depends on 11) The composition of claim 11 wherein the composition contains less than 3200 parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde, and is free of objectionable odor sensorially discernible to a human observer compared to that of a counterpart composition containing greater than 3200 parts of parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde. ### Claim 15 (depends on 1) The composition of claim 1 wherein the dimethicone copolyol sulfosuccinate has the formula: wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; X+ is an ammonium group derived from an amino alcohol, an amine ethoxylate or an amine propoxylate; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100. ### Claim 16 (depends on 15) The composition of claim 15 wherein the ammonium group, X+, is derived from at least one amine selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine and diglycolamine. ### Claim 17 (depends on 15) The composition of claim 15 wherein R is selected from the group consisting of: —(C2H4O)s—C2H4—; —(C3H6O)t—C3H6—; and —(C2H4O)v—(C3H6O)w—Y—; wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C2H4 or C3H6. ### Claim 18 (depends on 15) The composition of claim 15 wherein the composition contains less than 3200 parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde, and is free of objectionable odor sensorially discernible to a human observer compared to that of a counterpart composition containing greater than 3200 parts of parts per million of propionaldehyde and acid-releasable precursors of propionaldehyde.