IP Library Granted Patent US 9,215,895
Granted Patent B2
US 9,215,895 · App. 14/512,311 · Granted Dec 22, 2015

Nicotine salt formulations for aerosol devices and methods thereof

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Quick Facts
Patent No.
US 9,215,895
App. No.
14/512,311
Granted
Dec 22, 2015
Kind
B2
Abstract

A nicotine salt liquid formulation for generating an inhalable aerosol in an electronic cigarette comprising nicotine salt that forms about 0.5% to about 20% nicotine is provided.

Claims (44)

1. A method of delivering nicotine to a user comprising deploying an electronic cigarette comprising a nicotine formulation that comprises nicotine, an acid, wherein the acid comprises pyruvic acid, salicylic acid, sorbic acid, lauric acid, levulinic acid, or benzoic acid, and a biologically acceptable liquid carrier, wherein:

a. the nicotine formulation has a pH between 2.1-6.7;

b. the nicotine concentration is from about 2% (w/w) to about 6% (w/w);

c. operation of the electronic cigarette comprises heating at least a portion of the nicotine formulation to generate an inhalable aerosol comprising particle sizes from about 0.1 microns to about 5 microns; and

d. inhalation of the inhalable aerosol into the user's lungs over a period of about 5 minutes at a rate of about one inhalation per 30 seconds results in a nicotine plasma Tmax from about 3 min to about 8 min.

2. The method of claim 1 , wherein the nicotine plasma Tmax is from about 3 min to about 7 min, from about 3 min to about 6 min, from about 3 min to about 5 min, from about 3 min to about 4 min, from about 4 min to about 8 min, from about 4 min to about 7 min, from about 4 min to about 6 min, from about 4 min to about 5 min, from about 5 min to about 8 min, from about 5 min to about 7 min, from about 5 min to about 6 min, from about 6 min to about 8 min, from about 6 min to about 7 min, from about 7 min to about 8 min, less than about 8 min, less than about 7 min, less than about 6 min, less than about 5 min, less than about 4 min, about 8 min, about 7 min, about 6 min, about 5 min, about 4 min, or about 3 min.

3. The method of claim 1 , wherein the Tmax is determined based on at least three independent data sets.

4. The method of claim 1 , wherein the Tmax is a range of at least three independent data sets.

5. The method of claim 1 , wherein the Tmax is an average±a standard deviation of at least three independent data sets.

6. The method of claim 1 , wherein the nicotine formulation comprises a nicotine salt comprising nicotine and an acid.

7. The method of claim 6 , wherein nicotine formulation comprises monoprotonated nicotine.

8. The method of claim 1 , wherein the acid does not decompose at room temperature and does not decompose at the operating temperature of the electronic cigarette.

9. The method of claim 1 , wherein the acid comprises one carboxylic acid functional group.

10. The method of claim 1 , wherein the acid comprises benzoic acid.

11. The method of claim 1 , wherein the nicotine concentration is about 5% (w/w).

12. A method of delivering nicotine to a user comprising deploying an electronic cigarette comprising a nicotine formulation that comprises nicotine, an acid, wherein the acid comprises pyruvic acid, salicylic acid, sorbic acid, lauric acid, levulinic acid, or benzoic acid and a biologically acceptable liquid carrier, wherein:

a. the nicotine formulation has a pH between 2.1-6.7

b. operation of the electronic cigarette comprises heating at least a portion of the nicotine formulation to generate an inhalable aerosol comprising particle sizes from about 0.1 microns to about 5 microns;

c. inhalation of the inhalable aerosol into the user's lungs over a period of about 5 minutes at a rate of about one inhalation per 30 seconds results in a nicotine plasma Tmax from about 3 min to about 8 min;

d. the nicotine concentration is from about 2% (w/w) to about 6% (w/w);

e. the nicotine formulation comprises monoprotonated nicotine; and

f. the acid does not decompose at room temperature and does not decompose at the operating temperature of the electronic cigarette.

13. The method of claim 12 , wherein the acid comprises benzoic acid.

14. The method of claim 13 , wherein the nicotine concentration is about 5% (w/w).

15. A method of delivering nicotine to a user comprising deploying an electronic cigarette comprising a nicotine formulation comprising nicotine and benzoic acid in a biologically acceptable liquid carrier, wherein:

a. the nicotine formulation has a pH between 2.1-6.7;

b. the nicotine concentration is from about 2% (w/w) to about 6% (w/w);

c. operation of the electronic cigarette comprises heating at least a portion of the nicotine formulation to generate an inhalable aerosol comprising particle sizes from about 0.1 microns to about 5 microns; and

d. inhalation of the inhalable aerosol into the user's lungs over a period of about 5 minutes at a rate of about one inhalation per 30 seconds results in a nicotine plasma Tmax from about 5 min to about 8 min.

16. A cartridge for use with an electronic cigarette comprising a fluid compartment configured to be in fluid communication with a heating element, the fluid compartment comprising a nicotine formulation that comprises nicotine and an acid, wherein the acid comprises pyruvic acid, salicylic acid, sorbic acid, lauric acid, levulinic acid, or benzoic acid, and a biologically acceptable liquid carrier, wherein:

a. the nicotine formulation has a pH between 2.1-6.7

b. the nicotine concentration is from about 2% (w/w) to about 6% (w/w);

c. operation of the electronic cigarette comprises heating at least a portion of the nicotine formulation to generate an inhalable aerosol comprising particle sizes from about 0.1 microns to about 5 microns; and wherein

d. inhalation of the inhalable aerosol into the user's lungs over a period of about 5 minutes at a rate of about one inhalation per 30 seconds results in a nicotine plasma Tmax from about 3 min to about 8 min.

17. The cartridge of claim 16 , wherein the nicotine plasma Tmax is from about 3 min to about 7 min, from about 3 min to about 6 min, from about 3 min to about 5 min, from about 3 min to about 4 min, from about 4 min to about 8 min, from about 4 min to about 7 min, from about 4 min to about 6 min, from about 4 min to about 5 min, from about 5 min to about 8 min, from about 5 min to about 7 min, from about 5 min to about 6 min, from about 6 min to about 8 min, from about 6 min to about 7 min, from about 7 min to about 8 min, less than about 8 min, less than about 7 min, less than about 6 min, less than about 5 min, less than about 4 min, about 8 min, about 7 min, about 6 min, about 5 min, about 4 min, or about 3 min.

18. The cartridge of claim 16 , wherein the Tmax is determined based on at least three independent data sets.

19. The cartridge of claim 16 , wherein the Tmax is a range of at least three independent data sets.

20. The cartridge of claim 16 , wherein the Tmax is an average±a standard deviation of at least three independent data sets.

21. The cartridge of claim 16 , wherein the nicotine formulation comprises a nicotine salt comprising nicotine and an acid.

22. The cartridge of claim 21 , wherein nicotine formulation comprises monoprotonated nicotine.

23. The cartridge of claim 21 , wherein the acid does not decompose at room temperature and does not decompose at the operating temperature of the electronic cigarette.

24. The cartridge of claim 21 , wherein the acid comprises one carboxylic acid functional group.

25. The cartridge of claim 16 , wherein the acid comprises benzoic acid.

26. The cartridge of claim 16 , wherein the nicotine concentration is about 5% (w/w).

Assignments (16)
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2024
From: ALTER DOMUS (US) LLC
To: JUUL LABS, INC.; VMR PRODUCTS LLC; ENVENIO INC.
Reel/Frame 069185/0228 →
SECURITY INTEREST Recorded Jul 11, 2023
From: JUUL LABS, INC.; VMR PRODUCTS LLC; ENVENIO INC.
To: ALTER DOMUS (US) LLC
Reel/Frame 064252/0225 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 062114 FRAME: 0196. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Dec 23, 2022
From: JUUL LABS, INC.
To: JLI NATIONAL SETTLEMENT TRUST
Reel/Frame 062214/0142 →
SECURITY INTEREST Recorded Dec 10, 2022
From: JUUL LABS, INC.
To: JLI NATIONAL SETTLEMENT TRUST
Reel/Frame 062114/0195 →
RELEASE OF SECURITY INTEREST Recorded Oct 1, 2022
From: CORTLAND CAPITAL MARKET SERVICES LLC
To: JUUL LABS, INC.
Reel/Frame 061587/0947 →
SECURITY INTEREST Recorded Sep 30, 2022
From: JUUL LABS, INC.
To: ALTER DOMUS (US) LLC
Reel/Frame 061578/0865 →
RELEASE OF SECURITY INTEREST Recorded Jun 28, 2022
From: MUFG UNION BANK, N.A.
To: JUUL LABS, INC.
Reel/Frame 060446/0261 →
SECURITY INTEREST Recorded Aug 2, 2019
From: JUUL LABS, INC.
To: CORTLAND CAPITAL MARKET SERVICES LLC
Reel/Frame 049948/0881 →
PATENT SECURITY AGREEMENT Recorded Apr 26, 2019
From: JUUL LABS, INC.
To: MUFG UNION BANK, N.A.
Reel/Frame 049013/0519 →
TERMINATION OF PATENT SECURITY AGREEMENT Recorded Apr 26, 2019
From: MUFG UNION BANK, N.A
To: JUUL LABS, INC.
Reel/Frame 049013/0397 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR EXECUTION DATE PREVIOUSLY RECORDED AT REEL: 043544 FRAME: 0004. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Aug 6, 2018
From: PAX LABS, INC.
To: JUUL LABS, INC.
Reel/Frame 046732/0847 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2018
From: JUUL LABS, INC
To: MUFG UNION BANK, N.A.
Reel/Frame 045832/0328 →
CHANGE OF NAME Recorded Aug 14, 2017
From: PAX LABS, INC.
To: JUUL LABS, INC.
Reel/Frame 043544/0004 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2015
From: BOWEN, ADAM; XING, CHENYUE
To: PAX LABS, INC.
Reel/Frame 036349/0652 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 3, 2015
From: PLOOM, INC.
To: PAX LABS, INC.
Reel/Frame 035121/0328 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2014
From: BOWEN, ADAM; XING, CHENYUE
To: PLOOM, INC.
Reel/Frame 033933/0489 →