US 12,403,076 B2
Compositions comprising odorless 1,2-pentanediol
Ravikumar Pillai, Mahwah, NJ (US); Jürgen Siewert, Rollshausen (DE); Yonahha Sander, Höxter (DE); Gorsten Stephan, Holzminden (DE); Christian Wolter, Ottenstein (DE); and Oliver Lenz, Uslar (DE)
Assigned to SYMRISE AG, (DE)
Appl. No. 17/277,805
Filed by SYMRISE AG, Holzminden (DE)
PCT Filed Oct. 30, 2018, PCT No. PCT/EP2018/079729
§ 371(c)(1), (2) Date Mar. 19, 2021,
PCT Pub. No. WO2020/055761, PCT Pub. Date Mar. 26, 2020.
Claims priority of provisional application 62/733,744, filed on Sep. 20, 2018.
Prior Publication US 2022/0054378 A1, Feb. 24, 2022
Int. Cl. A61K 8/34 (2006.01); A61K 47/10 (2017.01); A61Q 5/02 (2006.01); A61Q 5/12 (2006.01); A61Q 19/00 (2006.01); A61Q 19/10 (2006.01); C11D 3/20 (2006.01)
CPC A61K 8/345 (2013.01) [A61K 47/10 (2013.01); A61Q 5/02 (2013.01); A61Q 5/12 (2013.01); A61Q 19/00 (2013.01); A61Q 19/10 (2013.01); C11D 3/2044 (2013.01)] 9 Claims
 
1. A composition comprising an 1,2-pentanediol amount, wherein said 1,2-pentanediol amount is obtained from a process comprising the following steps:
(a) providing at least one starting material selected from furfuryl alcohol and furfural;
(b) reacting at least one of said starting materials with hydrogen in the presence of a heterogeneous catalyst to form 1,2-pentanediol, wherein said heterogeneous catalyst comprises:
one or more metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium in metallic form and/or
one or more compounds of metals selected from the group consisting of platinum, rhodium, ruthenium, nickel, palladium and iridium; and
one or more support materials selected from the group consisting of activated carbon, aluminum oxide, silicon dioxide, and silicon carbide; and
(c) removing the 1,2-pentanediol thus obtained from the reaction mixture to produce said 1,2-pentanediol amount;
wherein said composition is formulated as a composition pH selected from the group consisting of skin care compositions, hair care compositions, personal care compositions, sun care compositions, oral care compositions, heavy duty powder detergents, heavy duty liquid detergents, light duty powder detergents, light duty liquid detergents, fabric softeners, manual dish wash agents and all-purpose cleaners;
wherein said 1,2-pentanediol contains less than 10 ppm of butyric acid or butyric acid ester impurities that develop into malodors when incorporated into a formulation comprising an alkaline pH value; and wherein said composition has improved odor stability over time when compared to an otherwise identical composition that comprises 1,2-pentanediol obtained from a different process.