# US 2019/0167553 A1 · Mixtures containing (e)-3-benzo[1,3]dioxol-5-yl-n,n-diphenyl-2-propenamide

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- Number: US 2019/0167553 A1
- Document ID: US20190167553A1
- Status: Published application
- Kind: A1
- Application number: 16/324,166
- Filed: 2016-08-09
- Published: 2019-06-06
- Earliest claimed: 2016-08-09
- Assignees: Symrise AG
- Applicants: Symrise AG
- Inventors: Benoit JOIN; Michael BACKES; Arnold MACHINEK; Ulrike SIMCHEN; Jenny WEISSBRODT; Jens FAHLE
- Web page: https://patentgrep.com/patent/US20190167553A1

## CPC

- A61K 8/42: Amides
- A23G 1/32: characterised by the composition {containing organic or inorganic compounds}
- A23G 4/06: characterised by the composition {containing organic or inorganic compounds}
- A61K 8/34: Alcohols
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/37: Esters of carboxylic acids
- A61K 8/4973: {with oxygen as the only hetero atom}
- A61K 8/922: {of vegetable origin}
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/004: {Aftersun preparations}
- A61Q 19/10: Washing or bathing preparations
- A61K 2800/244: Endothermic; Cooling; Cooling sensation
- A61K 2800/805: Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
- A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00)
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- 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)
- A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

Mixtures comprising a selected cooling active ingredient (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide and at least one other substance which acts as a solvent for (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide, wherein the substance is selected form the group consisting of benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, propylene glycol, further cooling active ingredients or mixtures thereof.

## Claims

### Claim 1

A mixture comprising:
a) (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide, and
b) a solvent selected from benzyl alcohol, 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, propylene glycol, and mixtures thereof.

### Claim 2 (depends on 1)

The mixture according to claim 1, wherein the solvent is benzyl alcohol, 2-phenyl ethanol or benzyl benzoate.

### Claim 3 (depends on 1)

The mixture according to claim 1, wherein the solvent is a binary system comprising two solvents selected from benzyl alcohol, 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, and propylene glycol.

### Claim 4 (depends on 3)

The mixture according to claim 3, wherein the solvent is a mixture of benzyl alcohol and a solvent selected from 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, and propylene glycol.

### Claim 5 (depends on 1)

The mixture according to claim 1, wherein the solvent is a ternary system comprising three solvents selected from benzyl alcohol, 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, and propylene glycol.

### Claim 6 (depends on 5)

The mixture according to claim 5, wherein the solvent is a ternary system comprising three solvents selected from benzyl alcohol and a solvent selected from 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, and propylene glycol.

### Claim 7 (depends on 1)

The mixture according to claim 1, wherein the solvent is a quaternary system comprising four solvents selected from benzyl alcohol, 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, and propylene glycol.

### Claim 8 (depends on 3)

The mixture according to claim 3, wherein the solvent is selected from one of the following binary combinations of solvents:
Benzyl alcohol and 2-phenyl ethanol,
Benzyl alcohol and benzyl benzoate,
Benzyl alcohol and diethyl succinate,
Benzyl alcohol and triethyl citrate,
Benzyl alcohol and triacetin,
Benzyl alcohol and ethanol,
Benzyl alcohol and peppermint oil,
Benzyl alcohol and anethol,
Benzyl alcohol and optamint,
Benzyl alcohol and propylene glycol,
Benzyl alcohol and menthol,
Benzyl alcohol and menthyl lactate,
Benzyl alcohol and menthol propylene glycol carbonate,
Benzyl alcohol and menthol ethylene glycol carbonate,
Benzyl alcohol and menthone glyceryl acetal,
Benzyl alcohol and menthane carboxylic acid esters and -amides,
2-phenyl ethanol and menthol propylene glycol carbonate,
Diethyl succinate and 2-phenyl ethanol,
Triacetin and benzyl benzoate,
Triethyl citrate and triacetin,
2-phenyl ethanol and peppermint oil,
2-phenyl ethanol and optamint,
Anethol and triacetin,
Peppermint oil and menthyl lactate,
Triacetin and menthone glyceryl acetal,
Optamint and menthyl lactate, and
Triethyl citrate and menthol ethylene glycol carbonate.

### Claim 9 (depends on 5)

The mixture according to claim 5, wherein the solvent is selected from one of the following ternary combinations of solvents:
Benzyl alcohol with:
2-phenyl ethanol and benzyl benzoate,
2-phenyl ethanol and diethyl succinate,
Triethyl citrate and triacetin,
Triacetin and ethanol,
Triacetin and peppermint oil,
Menthol ethylene glycol carbonate and anethol,
2-phenyl ethanol and optamint,
Optamint and propylene glycol,
Diethyl succinate and menthol,
Triacetin and menthyl lactate,
Anethol and menthol propylene glycol carbonate,
Triacetin and menthol ethylene glycol carbonate,
2-phenyl ethanol and menthone glyceryl acetal,
2-phenyl ethanol and menthane carboxylic acid esters and -amides,
2-phenyl ethanol and menthol propylene glycol carbonate,
Triacetin and benzyl benzoate,
2-phenyl ethanol and peppermint oil,
Anethol and triacetin,
Peppermint oil and menthyl lactate,
Triacetin and menthone glyceryl acetal,
Optamint and menthyl lactate,
Triethyl citrate and menthol ethylene glycol carbonate,
Benzyl benzoate and menthol ethylene glycol carbonate,
2-phenyl ethanol and triethyl citrate,
Triethyl citrate and diethyl succinate,
Peppermint oil and menthyl lactate,
Ethanol and menthyl lactate, or
Triethyl citrate and triacetin, and menthyl lactate,
Triacetin, 2-phenyl ethanol and peppermint oil,
2-phenyl ethanol, optamint and peppermint oil,
2-phenyl ethanol, triacetin and optamint,
Anethol, benzyl alcohol and triacetin,
2-phenyl ethanol and benzyl benzoate,
2-phenyl ethanol and diethyl succinate,
Triethyl citrate, triacetin and peppermint oil,
Optamint, triacetin and ethanol,
Triacetin, menthol ethylene glycol carbonate and anethol
2-phenyl ethanol, optamint and propylene glycol,
Diethyl succinate, triacetin and menthol,
Triacetin, benzyl benzoate and menthyl lactate,
Anethol, menthol propylene glycol carbonate and menthol ethylene glycol carbonate,
Triacetin, 2-phenyl ethanol and menthone glyceryl acetal,
Peppermint oil, 2-phenyl ethanol and menthane carboxylic acid esters and -amides,
Triacetin, 2-phenyl ethanol and menthol propylene glycol carbonate,
Menthyl lactate, 2-phenyl ethanol and peppermint oil,
Anethol, triacetin and menthone glyceryl acetal,
Optamint, benzyl benzoate and menthyl lactate, and
Benzyl benzoate, triethyl citrate and menthol ethylene glycol carbonate.

### Claim 10 (depends on 1)

The mixture according to claim 1, wherein component a) is present in the mixture in an amount of 2 wt.-% to 20 wt.-% and component b) is present in the mixture in an amount of 98 wt.-% to 80 wt.-%, related to the total mixture, provided that components a) and b) add up to 100 wt.-%.

### Claim 11 (depends on 1)

The mixture according to claim 1, wherein the mixture is stable up to 100° C.

### Claim 12 (depends on 1)

The mixture according to claim 1, wherein the (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide is present in the mixture in a stably dissolved form at 23° C.

### Claim 13 (depends on 1)

Particles obtained by subjecting the mixture according to claim 1 to a spray drying method or spray granuling method.

### Claim 14 (depends on 13)

A semi-finished product comprising the particles according to claim 13.

### Claim 15

(canceled)

### Claim 16

A method for dissolving (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide comprising: combining (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide with a solvent selected from benzyl alcohol, 2-phenyl ethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethol, optamint, propylene glycol, and mixtures thereof; and dissolving the (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide.

### Claim 17 (depends on 16)

The method of claim 16, wherein the (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide is dissolved at room temperature.

### Claim 18 (depends on 16)

The method of claim 16, wherein the (E)-3-benzo[1,3]dioxol-5-yl-N,N-diphenyl-2-propenamide is dissolved at 23° C.