US 12,440,435 B2
Solubilization of poorly soluble cooling substances
Jenny Weissbrodt, Holzminden (DE); Michael Backes, Holzminden (DE); Rita Lages, Bodenwerder (DE); and Olga Pauli, Holzminden (DE)
Assigned to SYMRISE AG, Holzminden (DE)
Appl. No. 17/257,898
Filed by SYMRISE AG, Holzminden (DE)
PCT Filed Jul. 6, 2018, PCT No. PCT/EP2018/068365
§ 371(c)(1), (2) Date Jan. 5, 2021,
PCT Pub. No. WO2020/007484, PCT Pub. Date Jan. 9, 2020.
Prior Publication US 2021/0267864 A1, Sep. 2, 2021
Int. Cl. A61K 8/42 (2006.01); A61K 8/11 (2006.01); A61K 8/37 (2006.01); A61Q 11/00 (2006.01); B01J 13/04 (2006.01)
CPC A61K 8/42 (2013.01) [A61K 8/11 (2013.01); A61K 8/37 (2013.01); A61K 8/375 (2013.01); A61Q 11/00 (2013.01); B01J 13/043 (2013.01)] 20 Claims
 
1. Cooling particles comprising:
(I) 5 to 40% by weight, based on a total weight of the cooling particles, of a cooling composition, the cooling composition comprising:
(A) 80 to 99% by weight, based on a total weight of the cooling composition, of a solvent component consisting of:
(i) 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate and/or (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate;
(ii) optionally, N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide; and
(iv) optionally, 0.5 to 8% by weight, based on a total weight of the solvent component, of medium-chain triglycerides; and
(B) 0.5 to 12% by weight, based on a total weight of the cooling composition, of a cooling agent that is (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide,
wherein the cooling agent (B) is dissolved in the solvent component (A) at room temperature; and
(II) a matrix material that encapsulates the cooling composition (I),
wherein the particles have an average particle diameter D50 of 10 to 2000 μm as determined by laser light diffraction according to ISO ISO13320:2009-10.