WO2023241103A1 - Composite nicotine salt, composite nicotine salt formulation and preparation method therefor and use thereof - Google Patents

Abstract

The present application relates to the technical field of electronic cigarettes, and in particular, to a composite nicotine salt, a composite nicotine salt formulation and a preparation method therefor and a use thereof. The composite nicotine salt provided by the present application comprises nicotine, a first organic acid and a second organic acid. The first organic acid is selected from aliphatic organic acids and/or aromatic organic acids, but does not comprise a phenolic acid. The second organic acid is selected from at least one of the following structural compounds a)-c): a) comprising a phenyl group substituted by at least one hydroxyl group, and a carboxyl group directly linked to the phenyl group; b) comprising a phenyl group substituted by at least one hydroxyl group, and a carboxyl group, wherein the carboxyl group is linked to the phenyl group by means of two carbon atoms; and c) comprising a phenyl group substituted by at least one hydroxyl group, and a carboxyl group, wherein the carboxyl group is linked to the phenyl group by means of three carbon atoms and a C6 ring. According to the composite nicotine salt provided by the present application, by adding a specific second organic acid, the consistency of comfort and satisfaction before and after smoking of the existing organic acid nicotine salt-containing electronic cigarettes can be greatly improved.

Description

Compound nicotine salt, complex nicotine salt preparation and preparation method and application thereof

Cross-references to related applications

This application requires the priority of the Chinese patent application submitted to the China Patent Office on June 16, 2022, with the application number 202210687044.0 and the invention name "Compound nicotine salt, compound nicotine salt formulation and preparation method and application thereof", The entire contents of which are incorporated herein by reference.

Technical field

The present invention relates to the technical field of electronic cigarettes, and specifically relates to a compound nicotine salt, a compound nicotine salt formulation and a preparation method and application thereof.

Background technique

E-cigarettes are also known as virtual cigarettes and electronic atomizers. E-cigarettes have a similar appearance and taste to cigarettes, but generally do not contain tar, suspended particles and other harmful ingredients in cigarettes. Nicotine and nicotine salts are the main sources of excitement and satisfaction for smokers smoking traditional cigarettes and e-cigarettes. It has been experimentally verified that nicotine salts of the same concentration, especially nicotine benzoate salt, can improve smoking comfort compared with free nicotine. and the duration of physiological satisfaction. Therefore, currently most e-cigarettes use nicotine salts, especially nicotine benzoate salts as the active ingredient.

However, after investigation, it was found that the current e-cigarettes containing organic acid nicotine salts (including nicotine benzoate) have poor consistency in comfort and satisfaction before and after smoking. After 100 puffs, the intensity and duration of physiological satisfaction decrease significantly. Some organic acid nicotine salt e-cigarette products also show a significant increase in irritation and a decrease in the duration of physiological satisfaction after 100 puffs. . That is to say, the existing organic acid nicotine salt e-cigarette products have the disadvantage that the comfort and satisfaction are significantly different between when you first start smoking and after a period of smoking.

Contents of the invention

The purpose of this application is to overcome the large difference in comfort and satisfaction of existing organic acid nicotine salt e-cigarette products when just starting to smoke and after smoking for a period of time, that is, the comfort and satisfaction are the same before and after smoking. To solve the defect of poor sex, a compound nicotine salt, a compound nicotine salt preparation and a preparation method and application thereof are provided.

In order to achieve the above objects, the present invention adopts the following technical solutions:

A composite nicotine salt, the raw materials forming the composite nicotine salt include nicotine and a first organic acid and a second organic acid; the first organic acid is selected from aliphatic organic acids and/or aromatic organic acids, But does not include phenolic acids;

The second organic acid is selected from at least one of the following structural compounds a)-c),

a) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group directly connected to the phenyl group;

b) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group, and the carboxyl group and the phenyl group are connected through 2 carbon atoms;

c) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group. The carboxyl group and the phenyl group are connected through 3 carbon atoms and 1 C6 ring.

Optionally, the compound of structure c) also includes at least one heteroatom between the three carbon atoms and the C6 ring.

Optionally, the second organic acid is selected from at least one of the following structural compounds:

Wherein R ₁ to R ₁₀ are the same or different, each independently selected from hydrogen, hydroxyl, C1-C10 alkoxy group, Represents a single or double bond.

It can be understood that for -COOH in the following structural formula, it can replace any substituent in R6-R10,

Optionally, the C1-C10 alkoxy group is selected from methoxy group, ethoxy group, and propoxy group.

optional,

The second organic acid is selected from caffeic acid (3,4-dihydroxycinnamic acid), ferulic acid (3-methoxy-4-hydroxycinnamic acid), sinapinic acid (3,5-dimethoxy- 4-hydroxycinnamic acid), p-coumaric acid (4-hydroxycinnamic acid), p-hydroxycinnamic acid (), isoferulic acid (3-hydroxy-4-methoxycinnamic acid), gallic acid (3,4 ,5-trihydroxybenzoic acid), chlorogenic acid ((1S,3R,4R,5R)-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl] At least one of [oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid).

Optionally, the first organic acid is selected from at least one selected from benzoic acid, malic acid, levulinic acid, and myristanoic acid.

Optionally, the second organic acid accounts for 1%-15% of the total mass of the first organic acid and the second organic acid;

The mass ratio of the total mass of the first organic acid and the second organic acid to nicotine (0.6-1.5): 1.

The present application also provides a complex nicotine salt formulation, including the above-mentioned complex nicotine salt.

Optionally, the complex nicotine salt formulation further includes a carrier solvent. Optionally, the carrier solvent includes propylene glycol and/or glycerin. Optionally, the mass ratio of propylene glycol and glycerin is 1: (0.1-10).

Optionally, the complex nicotine salt formulation also includes spices, and optionally, the mass ratio of spices to nicotine is (10-0.1):1.

Optionally, the complex nicotine salt formulation exists in the form of a complex nicotine salt formulation solution, and the mass concentration of nicotine in the complex nicotine salt formulation solution is 1%-50%.

The present application also provides a method for preparing the above-mentioned compound nicotine salt formulation, which includes the following steps:

It is obtained by mixing nicotine, the first organic acid, the second organic acid and the carrier solvent, then heating and stirring.

Optionally, the first organic acid, the second organic acid and the carrier solvent are mixed, stirred at the first heating temperature, cooled, and then nicotine is added and stirred at the second heating temperature to obtain the composite nicotine salt. Concoctions.

Optionally, the first heating temperature is 40-70°C, and the stirring time is 1-10 min;

The second heating temperature is 20-100°C, and the stirring time is 5-180 min.

Optionally, the step of diluting the obtained complex nicotine salt formulation with a carrier solvent is also included.

This application also provides an application of the above-mentioned complex nicotine salt or the above-mentioned complex nicotine salt formulation in an atomization device.

Optionally, the atomization device is an electronic cigarette.

Beneficial effects of this application:

The compound nicotine salt provided in this application is formed from nicotine and a first organic acid and a second organic acid. The first organic acid is a common The organic acid is selected from aliphatic organic acids and/or aromatic organic acids, but does not include phenolic acids; the second organic acid is selected from phenolic acids and has at least one of the structures a)-c). This application adds specific The second organic acid can greatly improve the consistency of comfort and satisfaction before and after smoking in existing organic acid nicotine salt e-cigarettes.

Further, optionally in this application, the second organic acid is selected from caffeic acid, ferulic acid, sinapinic acid, p-coumaric acid, p-hydroxycinnamic acid, isoferulic acid, gallic acid, and chlorogenic acid. of at least one. This application selects the above-mentioned specific second organic acid and cooperates with nicotine and the first organic acid to further improve the consistency of comfort and satisfaction of the organic acid nicotine salt electronic cigarette before and after smoking.

Description of the drawings

In order to more clearly explain the specific embodiments of the present application or the technical solutions in the prior art, the drawings needed to be used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings in the following description The drawings illustrate some embodiments of the present application. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without exerting creative efforts.

Figure 1 is a change curve of the average heart rate data of a tester using the nicotine salt formulation prepared in Example 1;

Figure 2 is a change curve of the average heart rate data of the tester using the nicotine salt formulation prepared in Example 2;

Figure 3 is a change curve of the average heart rate data of a tester using the nicotine salt formulation prepared in Example 3;

Figure 4 is a change curve of the average heart rate data of the tester using the nicotine salt formulation prepared in Example 4;

Figure 5 is a change curve of the average heart rate data of a tester using the nicotine salt formulation prepared in Example 5;

Figure 6 is a change curve of the average heart rate data of the tester using the nicotine salt formulation prepared in Example 6;

Figure 7 is a change curve of the average heart rate data of a tester using the nicotine salt formulation prepared in Example 7;

Figure 8 is a change curve of the average heart rate data of the tester using the nicotine salt formulation prepared in Example 8;

Figure 9 is a change curve of the average heart rate data of a tester using the nicotine salt formulation prepared in Example 9;

Figure 10 is a change curve of the average heart rate data of the tester using the nicotine salt formulation prepared in Example 10;

Figure 11 is a change curve of the average heart rate data of the nicotine salt formulation prepared by the tester using Comparative Example 1;

Figure 12 is a change curve of the average heart rate data of the nicotine salt formulation prepared by the tester using Comparative Example 2;

Figure 13 is a change curve of the average heart rate data of the nicotine salt formulation prepared by the tester using Comparative Example 3;

Figure 14 is a change curve of the average heart rate data of the nicotine salt formulation prepared by the tester using Comparative Example 4;

Figure 15 is a change curve of the average heart rate data of the nicotine salt formulation prepared by the tester using Comparative Example 5;

Figure 16 is a curve showing the change in nicotine content of the nicotine salt formulation prepared in Examples 1-10 with the number of puffs when smoked using a cigarette rod;

Figure 17 is a graph showing the variation curve of nicotine content with the number of puffs of the nicotine salt formulation prepared in Comparative Examples 1-5 when smoked using a cigarette rod.

Detailed ways

The following examples are provided to better understand the present application. They are not limited to the best implementation mode, and do not limit the content and protection scope of the present application. Anyone who is inspired by this application or uses this application will Any product that is identical or similar to the present application by combining it with other features of the prior art falls within the protection scope of the present application.

If no specific experimental steps or conditions are specified in the examples, the procedures can be carried out according to the conventional experimental steps or conditions described in literature in the field. If the manufacturer of the reagents or instruments used is not indicated, they are all conventional reagent products that can be purchased commercially.

Example 1

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g chlorogenic acid into a stoppered flask, add 3g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), and stir at 60°C for 5 minutes until complete Dissolve, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) into the above solution and stir evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 2

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.8g benzoic acid and 0.04g chlorogenic acid into a stoppered flask, add 3.16g mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5), and stir at 60°C for 5 minutes until Completely dissolve, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) Add to the above solution and stir evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 3

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.65g levulinic acid and 0.03g ferulic acid to a stoppered flask, add 3.32g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), and stir at 60°C for 5 minutes. Until completely dissolved, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5 ) was added to the above solution and stirred evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 4

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g caffeic acid into a stoppered flask, add 3.0g mixed solvent of propylene glycol and glycerol (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5), and stir at 60°C for 5 minutes until complete Dissolve, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) into the above solution and stir evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 5

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g gallic acid into a stoppered flask, add 3.0g mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5), and stir at 60°C for 5 minutes until complete Dissolve, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) into the above solution and stir evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 6

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g sinapinic acid into a stoppered flask, add 3.0g mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), and stir at 60°C for 5 minutes until complete Dissolve, cool and add 1g of nicotine slowly Drop into the above solution, stir at 30°C for 30 minutes, cool to room temperature, add 45g of a mixed solvent of propylene glycol and glycerol (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) into the above solution and stir evenly to obtain The compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 7

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g p-coumaric acid into a stoppered flask, add 3.0g mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5), and stir at 60°C for 5 minutes Until completely dissolved, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5 ) was added to the above solution and stirred evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 8

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.95g benzoic acid and 0.05g isoferulic acid into a stoppered flask, add 3.0g mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), and stir at 60°C for 5 minutes Until completely dissolved, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5 ) was added to the above solution and stirred evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 9

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 1.2g tetradecanoic acid and 0.05g isoferulic acid to a stoppered flask, add 2.75g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:6), and heat at 70°C. Stir for 2 minutes until completely dissolved. After cooling, slowly drop 1g of nicotine into the above solution. Stir at 40°C for 60 minutes. After cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5 :6) Add to the above solution and stir evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Example 10

This embodiment provides a method for preparing a compound nicotine salt formulation, which includes the following steps:

Add 0.60g malic acid and 0.05g isoferulic acid into a stoppered flask, add 3.35g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:7), and stir at 60°C for 5 minutes. Until completely dissolved, after cooling, slowly drop 1g of nicotine into the above solution, stir at 30°C for 30 minutes, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:7 ) was added to the above solution and stirred evenly to obtain the compound nicotine salt formulation (the mass fraction of nicotine in the compound nicotine salt formulation is 2%).

Comparative example 1

This comparative example provides a preparation method of nicotine salt formulation, including the following steps:

Add 1.0g benzoic acid to the stoppered flask, add 3.00g of a mixed solvent of propylene glycol and glycerol (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), stir at 60°C for 5 minutes until completely dissolved, and cool down. 1g of nicotine was slowly dropped into the above solution, stirred at 30°C for 30 minutes, and after cooling to room temperature, 45g of a mixed solvent of propylene glycol and glycerol (the mass ratio of propylene glycol and glycerol in the mixed solvent was 5:5) was added to the above solution. Stir evenly to obtain the nicotine salt formulation (the mass fraction of nicotine in the nicotine salt formulation is 2%).

Comparative example 2

This comparative example provides a preparation method of nicotine salt formulation, including the following steps:

Add 0.84g benzoic acid to the stoppered flask, add 3.16g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), stir at 60°C for 5 minutes until completely dissolved, and cool down. 1g of nicotine was slowly dropped into the above solution, stirred at 30°C for 30 minutes, and after cooling to room temperature, 45g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerol in the mixed solvent was 5:5) was added to the above solution. Stir evenly to obtain the nicotine salt formulation (the mass fraction of nicotine in the nicotine salt formulation is 2%).

Comparative example 3

This comparative example provides a preparation method of nicotine salt formulation, including the following steps:

Add 0.68g levulinic acid to the stoppered flask, add 3.32g of a mixed solvent of propylene glycol and glycerin (the mass ratio of propylene glycol and glycerin in the mixed solvent is 5:5), stir at 60°C for 5 minutes until completely dissolved, and cool Slowly drop 1g of nicotine into the above solution, stir for 30 minutes at 30°C, and after cooling to room temperature, add 45g of a mixed solvent of propylene glycol and glycerol (the mass ratio of propylene glycol and glycerol in the mixed solvent is 5:5) into the above solution. and stir evenly to obtain the composite nicotine salt formulation (the mass fraction of nicotine in the nicotine salt formulation is 2%).

Comparative example 4

This comparative example provides a method for preparing a nicotine salt formulation. The difference from Example 9 is that 1.25g of myristanoic acid is added and isoferulic acid is not added.

Comparative example 5

This comparative example provides a method for preparing a nicotine salt formulation. The difference from Example 10 is that 0.65g of malic acid is added and isoferulic acid is not added.

Test example 1

The nicotine salt formulations prepared in the above embodiments and comparative examples were respectively evaluated for the satisfaction consistency effect. The evaluation method includes the following steps:

Five testers are selected. The testers need to quit nicotine 24 hours in advance. The nicotine salt formulation to be tested must be prepared and canned cigarette cartridges 24 hours in advance. The tester started the test at 10 a.m.: the heart rate test started from 0 seconds, and at the same time, he used the RELX5 generation cigarette rod to take 5 puffs (the first 5 puffs) at 0 seconds, with each puff taking 3 seconds and the interval between each puff being 5 seconds. During this period, the tester's heart rate was tested, and the heart rate value was recorded every 5 seconds. The test time was 280 seconds in total; after the tester completed the first 5 puffs of the test, the cigarette cartridge was smoked with a smoking machine for 180 puffs (each puff was 3 seconds, and the interval between each puff was 27s), at 10 a.m. the next day, the subject's heart rate test was started from 0 seconds, and at the same time, the subject was asked to use the RELX5 generation cigarette rod to smoke the cigarette cartridge that had been smoked through the smoking machine yesterday for 180 puffs at 0 seconds. Take 5 puffs (5 puffs after 180 puffs), each puff takes 3 seconds, and the interval between each puff is 5 seconds. During this period, the subject's heart rate is tested, and the heart rate value is recorded every 5 seconds. The test time is 280 seconds in total; the first 5 seconds are obtained The test results of the mouth and 5 mouths after 180 mouths are used as the basis for evaluating the consistency effect of satisfaction before and after. The test results are shown in Figure 1-15.

This application reflects the physiological satisfaction effect of different nicotine formulations by using the average change curve of the tester's heart rate data. From the test results, it can be seen that the satisfaction consistency evaluation effect of the nicotine salt formulation prepared in the embodiment of the application Significantly better than the comparison example.

Test example 2

The nicotine salt formulations prepared in the above examples and comparative examples were added to the same electronic cigarette device, and 10 e-cigarette sensory evaluation expert evaluators conducted a comfort consistency test on the nicotine salt formulations. A sensory quality evaluation form uses a dark scoring method to smoke the nicotine salt formulation. The smoking method is:

The evaluator started the test at 10 a.m.: First, he took 3 puffs (the first 3 puffs) using the RELX5 generation cigarette rod. Each puff took 3 seconds, and the interval between each puff was 5 seconds. When the evaluator finished the first 3 puffs, he took 3 puffs. The cartridge was smoked with a smoking machine for 180 puffs (each puff was 3 seconds, and the interval between each puff was 27 seconds). At 10 a.m. the next day, the evaluator was asked to use the RELX5 generation cigarette rod to smoke the cartridge that had been smoked through the smoking machine yesterday for 180 puffs. , take 3 puffs (3 puffs after 180 puffs), each puff takes 3 seconds, and the interval between each puff is 5 seconds.

Score and evaluate based on the three comfort sensory effect evaluation indicators in Table 1, among which the three sensory effect evaluation indicators include nasal irritation, oral irritation, and throat irritation; and according to the different degrees of impact of each evaluation index on sensory quality Assign different points. Among them, no irritation means that the nasal cavity, oral cavity, and throat are not irritated, and the comfort is the best; mild irritation means that the nasal cavity, oral cavity, and throat are irritated, and the comfort is acceptable; moderate irritation means that the nasal cavity, oral cavity, and throat are irritated, and the comfort is acceptable; moderate irritation means that the nasal cavity, mouth, and throat are irritated, and the comfort is acceptable; Severe irritation means excessive irritation to the nasal cavity, mouth, and throat, which is extremely uncomfortable and completely unacceptable.

The test results are shown in Table 1 (the scoring value is the average scoring value).

Table 1

It can be seen from the test results in Table 1 that the comfort consistency evaluation effect of the nicotine salt formulation prepared in the embodiment of the present application is significantly better than that of the comparative example.

Test example 3

RELX 5th generation cigarette rod was used to test the nicotine smoke release content of Examples 1-10 and Comparative Examples 1-5. The total number of puffs tested was 200 puffs. After every 50 puffs of smoke were collected using a Cambridge filter, the nicotine content was detected. The obtained average value of nicotine smoke content intuitively reflects the release pattern of nicotine smoke, and also verifies the test results of sensory satisfaction. The test results are shown in Figures 16-17. Figures 16-17 also verify the results prepared in the embodiments of the present application. The nicotine salt formulation's satisfaction consistency evaluation effect is significantly better than that of the comparative example.

Obviously, the above-mentioned embodiments are only examples for clear explanation and are not intended to limit the implementation. For the field For those of ordinary skill, other different forms of changes or changes can be made on the basis of the above description. An exhaustive list of all implementations is neither necessary nor possible. The obvious changes or modifications derived therefrom are still within the protection scope of the present invention.

Claims (17)

A composite nicotine salt, characterized in that the raw materials forming the composite nicotine salt include nicotine and a first organic acid and a second organic acid; the first organic acid is selected from aliphatic organic acids and/or aromatic acids group of organic acids, but excluding phenolic acids; The second organic acid is selected from at least one of the following structural compounds a)-c), a) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group directly connected to the phenyl group; b) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group, and the carboxyl group and the phenyl group are connected through 2 carbon atoms; c) Includes a phenyl group substituted by at least one hydroxyl group and a carboxyl group. The carboxyl group and the phenyl group are connected through 3 carbon atoms and 1 C6 ring. The compound nicotine salt according to claim 1, wherein the compound of structure c) further includes at least one heteroatom between the three carbon atoms and the C6 ring. The compound nicotine salt according to claim 1 or 2, characterized in that the second organic acid is selected from at least one of the following structural compounds:
Wherein R ₁ to R ₁₀ are the same or different, each independently selected from hydrogen, hydroxyl, C1-C10 alkoxy group, Represents a single or double bond. The compound nicotine salt according to any one of claims 1 to 3, characterized in that the C1-C10 alkoxy group is selected from the group consisting of methoxy group, ethoxy group and propoxy group. The compound nicotine salt according to any one of claims 1 to 4, characterized in that the second organic acid is selected from the group consisting of caffeic acid, ferulic acid, sinapinic acid, p-coumaric acid, p-hydroxycinnamic acid, and iso-cinnamic acid. At least one of ferulic acid, gallic acid, and chlorogenic acid. The compound nicotine salt according to any one of claims 1 to 5, wherein the first organic acid is selected from at least one selected from the group consisting of benzoic acid, malic acid, levulinic acid, and myristanoic acid. The compound nicotine salt according to any one of claims 1-6, wherein the second organic acid accounts for 1%-15% of the total mass of the first organic acid and the second organic acid; The mass ratio of the total mass of the first organic acid and the second organic acid to nicotine (0.6-1.5): 1. A compound nicotine salt preparation, characterized in that it includes the compound nicotine salt described in any one of claims 1-7. The complex nicotine salt formulation according to claim 8, wherein the complex nicotine salt formulation further includes a carrier solvent. The complex nicotine salt formulation of claim 9, wherein the carrier solvent includes propylene glycol and/or glycerin. The compound nicotine salt formulation according to any one of claims 8 to 10, wherein the compound nicotine salt formulation exists in the form of a compound nicotine salt formulation solution, and the compound nicotine salt formulation The mass concentration of nicotine in the product solution is 1%-50%. The preparation method of the compound nicotine salt formulation according to any one of claims 8-11, characterized in that it includes the following steps: It is obtained by mixing nicotine, the first organic acid, the second organic acid and the carrier solvent, then heating and stirring. The preparation method of the composite nicotine salt formulation according to any one of claims 8 to 11, characterized in that the first organic acid, the second organic acid and the carrier solvent are mixed, stirred at the first heating temperature, and cooled. , then add nicotine and stir at the second heating temperature to obtain the complex nicotine salt formulation. The preparation method according to claim 13, characterized in that the first heating temperature is 40-70°C, and the stirring time is 1-10 min; The second heating temperature is 20-100°C, and the stirring time is 5-180 min. The preparation method according to any one of claims 12 to 14, further comprising the step of diluting the obtained compound nicotine salt formulation with a carrier solvent. Application of the complex nicotine salt according to any one of claims 1 to 7 or the complex nicotine salt formulation according to any one of claims 8 to 11 in an atomization device. The application according to claim 16, characterized in that the atomization device is an electronic cigarette.