Solubilization of poorly soluble cooling substances

Patent metadata

Field	Value
Publication number	US-12440435-B2
Application number	US-201817257898-A
Country	US
Kind code	B2
Filing date	Jul 6, 2018
Priority date	Jul 6, 2018
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

The present invention relates to a cooling composition for producing cooling particles comprising a solvent component and dissolved therein (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide. The present invention further relates to cooling particles comprising a cooling composition according to the invention, oral preparations comprising cooling particles, new uses of cooling particles, a process for the production of cooling particles as well as the use of a solvent component for dissolving cooling agents.

First claim

The invention claimed is:

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.

2. The cooling particles of claim 1 , wherein the matrix material comprises starch; starch derivatives; cellulose; cellulose derivatives; polysaccharides other than cellulose, cellulose derivatives, starch, and starch derivatives; natural fats; natural waxes; proteins; or a combination thereof.

3. The cooling particles of claim 1 , wherein the cooling particles are produced by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, or a coating process.

4. The cooling particles of claim 1 , wherein the N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide is present in the solvent component (A).

5. The cooling particles of claim 4 , wherein the N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide is (1R,2S,5R)-N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide.

6. The cooling particles of claim 1 , wherein the medium-chain triglycerides are present in the solvent component (A).

7. The cooling particles of claim 1 , wherein the 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate is present in the solvent component (A) as 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate.

8. The cooling particles of claim 1 , wherein the (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate is present in the solvent component (A) as [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] (2S)-2-hydroxypropanoate.

9. The cooling particles of claim 1 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 comprising:
(i) 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate and/or 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate;
(ii) (1R,2S,5R)-N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide; and
(iii) optionally, 0.5 to 8% by weight, based on a total weight of the solvent component, of medium-chain triglycerides; and

(B) 1.5 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) of (I) (A),
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.

10. The cooling particles of claim 9 , wherein the medium-chain triglycerides are present in solvent component (A).

11. The cooling particles of claim 10 , wherein the medium-chain triglycerides are present in an amount of 4 to 7.5% by weight, based on the total weight of the solvent component (A).

12. Cooling particles comprising:
(I) 10 to 30% 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 comprising:
(i) 2 to 20% by weight, based on a total weight of the solvent component, of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate;
(ii) 55 to 75% by weight, based on the total weight of the solvent component, of (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate; and
(iii) 15 to 35% by weight, based on the total weight of the solvent component, of N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide; and

(B) 1 to 10% by weight, based on the 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; and

(II) a matrix material that encapsulates the cooling composition (I),
wherein the cooling agent (B) is dissolved in the solvent component (A) at room temperature, and
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.

13. The cooling particles of claim 12 , wherein the solvent component (A) further comprises 0.5 to 8% by weight, based on the total weight of the solvent component (A), of medium-chain triglycerides.

14. The cooling particles of claim 13 , wherein the medium-chain triglycerides are present in an amount of 4 to 7.5% by weight, based on the total weight of the solvent component (A).

15. The cooling particles of claim 12 , wherein the solvent component (A) comprises:
(i) 4 to 15% by weight, based on a total weight of the solvent component, of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate;
(ii) 60 to 70% by weight, based on a total weight of the solvent component, of (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate; and
(iii) 20 to 30% by weight, based on a total weight of the solvent component, of N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide.

16. The cooling particles of claim 15 , wherein the solvent component (A) further comprises 0.5 to 8% by weight, based on the total weight of the solvent component (A), of medium-chain triglycerides.

17. The cooling particles of claim 12 , wherein the solvent component (A) comprises:
(i) 6.44 to 11.8% by weight, based on a total weight of the solvent component, of 2-hydroxypropyl (2-isopropyl-5-methyl-cyclohexyl) carbonate;
(ii) 63 to 67% by weight, based on a total weight of the solvent component, of (2-isopropyl-5-methyl-cyclohexyl) 2-hydroxypropanoate; and
(iii) 23 to 27% by weight, based on a total weight of the solvent component, of N-ethyl-2-isopropyl-5-methyl-cyclohexanecarboxamide.

18. The cooling particles of claim 17 , wherein the solvent component (A) further comprises 0.5 to 8% by weight, based on the total weight of the solvent component (A), of medium-chain triglycerides.

19. Cooling particles comprising:
(I) 10 to 30% 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 comprising:
(i) 4 to 15% by weight, based on a total weight of the solvent component, of 2-hydroxypropyl [(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl] carbonate;
(ii) 60 to 70% by weight, based on the total weight of the solvent component, of [(1R,2S,5R)-2-isopropyl-5-

Assignees

• Symrise Ag

Inventors

• Weissbrodt Jenny
• Backes Michael
• Lages Rita
• Pauli Olga

Classifications

• B01J13/043

  Drying and spraying · CPC title

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title

• A61K8/11

  Encapsulated compositions · CPC title