# US 2014/0194646 A1 · Alkyl Lactyllactates and Processes of Making the Same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0194646 A1 - Document ID: US20140194646A1 - Status: Published application - Kind: A1 - Application number: 14/146,662 - Filed: 2014-01-02 - Published: 2014-07-10 - Earliest claimed: 2006-07-06 - Assignees: Stepan Company - Applicants: Stepan Company - Inventors: David R. Allen; Anatoliy A. Dameshek; Branko Sajic; Irene Shapiro; Xue Min Dong; Christopher D. Smith; Jacqueline M. Pytel; Jeremy Weitgenant - Web page: https://patentgrep.com/patent/US20140194646A1 ## CPC - C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds - A61K 8/37: Esters of carboxylic acids - A61Q 5/02: Preparations for cleaning the hair - A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00) - A61Q 19/10: Washing or bathing preparations - C07C 67/03: by reacting an ester group with a hydroxy group - C07C 69/68: Lactic acid esters - C07B 2200/07: Optical isomers - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 - C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F) ## Abstract Provided are alkyl lactyllactate compositions that can be prepared from (1) lactide or alternatively lactic acid, and (2) a hydroxyl containing compound such as an alcohol, preferably a fatty alcohol or an alkoxylated alcohol, with (3) an acid catalyst. Preferably, the fatty alcohol contains from about 6 to 18 carbon atoms, such as lauryl alcohol. The alkyl lactyllactates can be used as surfactants, emulsifiers, skin feel agents, film formers, thickeners, rheological modifiers, etc., for personal care and other application areas. Compositions containing at least one alkyl lactyllactate are also provided. The compositions can further contain at least one surfactant. ## Claims ### Claim 1 A process for making an alkyl lactyllactate comprising the steps of: providing a mixture comprising lactide, at least one hydroxyl containing compound, and at least one acid catalyst, wherein the lactide and the at least one hydroxyl containing compound are present in equivalent molar amounts and wherein no solvent is added to the mixture; and reacting the lactide and the at least one hydroxyl containing compound at a temperature within the range of from about 15° C. to about 150° C. ### Claim 2 (depends on 1) The process of claim 1, wherein the temperature is within the range of from about 20° C. to about 70° C. ### Claim 3 (depends on 1) The process claim 1, wherein the at least one acid catalyst is H2SO4, HCl, p-toluenesulfonic acid, an ionomer of sulfonated tetrafluoroethylene copolymer, or a mixture thereof. ### Claim 4 (depends on 1) The process of claim 1, wherein the lactide is L-lactide, meso-lactide, racemic lactide, or a mixture thereof. ### Claim 5 (depends on 1) The process of claim 1, wherein the lactide is a mixture of L-lactide and meso-lactide. ### Claim 6 (depends on 5) The process of claim 5, wherein the mixture comprises from about 15% to about 70% of L-lactide and from about 85% to about 30% of meso-lactide, based on the total weight of the mixture. ### Claim 7 (depends on 1) The process of claim 1, wherein the at least one hydroxyl containing compound comprises at least one primary hydroxyl group. ### Claim 8 (depends on 7) The process of claim 7, wherein the at least one hydroxyl containing compound is substantially free of secondary and tertiary hydroxyl groups. ### Claim 9 (depends on 1) The process of claim 1, wherein the at least one hydroxyl containing compound is a fatty alcohol having from about 6 to about 18 carbon atoms. ### Claim 10 (depends on 9) The process of claim 9, wherein the fatty alcohol is lauryl alcohol. ### Claim 11 (depends on 1) The process of claim 1, wherein the at least one hydroxyl containing compound is alkoxylated. ### Claim 12 (canceled) ### Claim 13 (depends on 1) The process of claim 1, further comprising the step of: forming a clear, homogeneous liquid. ### Claim 14 (depends on 1) The process of claim 1, wherein the process provides a yield of at least about 95%. ### Claim 15 (depends on 1) The product produced by the process of claim 1. ### Claim 16 (depends on 15) The product of claim 15 wherein the product comprises at least about 90% or greater of at least one alkyl lactyllactate, based on the total weight of the product. ### Claim 17 (depends on 16) The product of claim 16, wherein the at least one alkyl lactyllactate comprises at least one L-alkyl lactyllactate. ### Claim 18 (depends on 17) The product of claim 17, wherein the at least one alkyl lactyllactate is substantially free of other stereoisomers of the alkyl lactyllactate. ### Claim 19 (depends on 16) The product of claim 16, wherein the at least one alkyl lactyllactate comprises at least one L,D/D,L-racemic alkyl lactyllactate. ### Claim 20 (depends on 16) The product of claim 16, wherein the at least one alkyl lactyllactate comprises at least one L-alkyl lactyllactate and at least one L,D/D,L-racemic alkyl lactyllactate. ### Claim 21 (depends on 15) The product of claim 15 comprises less than about 5% of at least one alkyl lactate and less than about 5% of the at least one hydroxyl containing compound, based on the total weight of the product. ### Claim at position 22 22-49. (canceled) ### Claim 50 (depends on 1) The method of claim 1, wherein the at least one hydroxyl containing compound is an alcohol.