WO2024087160A1 - 复合烟碱盐、复合烟碱盐调配物及其制备方法和应用 - Google Patents

复合烟碱盐、复合烟碱盐调配物及其制备方法和应用 Download PDF

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WO2024087160A1
WO2024087160A1 PCT/CN2022/128217 CN2022128217W WO2024087160A1 WO 2024087160 A1 WO2024087160 A1 WO 2024087160A1 CN 2022128217 W CN2022128217 W CN 2022128217W WO 2024087160 A1 WO2024087160 A1 WO 2024087160A1
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nicotine salt
composite
nicotine
salt formulation
composite nicotine
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PCT/CN2022/128217
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English (en)
French (fr)
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宁静
廖晓祥
周勇
杜振兴
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思摩尔国际控股有限公司
深圳麦克韦尔科技有限公司
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Priority to PCT/CN2022/128217 priority Critical patent/WO2024087160A1/zh
Publication of WO2024087160A1 publication Critical patent/WO2024087160A1/zh

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    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/16Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24FSMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F47/00Smokers' requisites not otherwise provided for

Definitions

  • 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 and application thereof.
  • Electronic cigarettes also known as virtual cigarettes and electronic atomizers, have a similar appearance and taste to cigarettes, but generally do not contain tar, suspended particulates and other harmful ingredients in cigarettes.
  • nicotine salts are the most important addiction-relieving ingredients of all tobacco products.
  • process and quality research of nicotine salt formulations has always been a hot research area.
  • the purpose of the present application is to overcome the defect that the nicotine salt of the existing electronic cigarette will form smoke stains on the surface of the electronic cigarette heating element after long-term smoking, which will cause smoking odor and reduce the sensory experience, and further provide a composite nicotine salt, a composite nicotine salt formulation and its preparation method and application.
  • a composite nicotine salt wherein the raw materials for forming the composite nicotine salt include nicotine, an organic acid and an additive, wherein the additive has the structure shown below:
  • R 1 -R 3 are each independently selected from hydrogen and hydroxyl, and at least two substituents among R 1 -R 3 are hydroxyl;
  • R 4 -R 7 are each independently selected from hydrogen and hydroxyl, and at least two substituents among R 4 -R 7 are hydroxyl;
  • R 1 , R 3 , R 5 and R 6 are hydroxyl groups
  • R 2 and R 7 are hydrogen
  • R 4 is hydrogen or hydroxyl.
  • R 1 , R 3 , R 4 , R 5 and R 6 are hydroxyl groups, and R 2 and R 7 are hydrogen groups.
  • R 1 , R 3 , R 5 , and R 6 are hydroxyl groups
  • R 2 , R 4 , and R 7 are hydrogen groups.
  • the stereo configuration of the carbon chiral center at * is independently R configuration or S configuration.
  • the additive is selected from at least one of catechin, epicatechin, gallocatechin and epigallocatechin.
  • the organic acid is selected from aliphatic organic acids and/or aromatic organic acids.
  • the aliphatic organic acid is selected from C1-C10 aliphatic organic carboxylic acid; the aromatic organic acid is selected from C6-C14 aliphatic organic carboxylic acid; optionally, the aliphatic organic acid is selected from C1-C5 aliphatic organic carboxylic acid; the aromatic organic acid is selected from C6-C8 aliphatic organic carboxylic acid, optionally, the C1-C5 aliphatic organic carboxylic acid contains 1-2 carboxyl groups, and the C6-C8 aliphatic organic carboxylic acid contains 1-2 carboxyl groups.
  • the organic acid is selected from at least one of benzoic acid, malic acid, levulinic acid and lactic acid.
  • the mass ratio of the additive to nicotine is (0.01-5):100;
  • the ratio of the molar amount of the organic acid calculated as carboxylate to the molar amount of nicotine is (0.5-2):1.
  • the present application also provides a composite nicotine salt formulation, comprising the composite nicotine salt described above.
  • the composite nicotine salt formulation further includes a carrier solvent.
  • the carrier solvent is selected from C1-C10 fatty alcohols, wherein the fatty alcohols contain 1-3 hydroxyl groups.
  • the carrier solvent is selected from C1-C5 fatty alcohols, wherein the fatty alcohols contain 1-3 hydroxyl groups.
  • the carrier solvent includes propylene glycol (PG) and/or vegetable glycerol (VG).
  • PG propylene glycol
  • VG vegetable glycerol
  • the present application does not specifically limit the ratio of the two.
  • the volume ratio of propylene glycol and vegetable glycerol is (0.1-10): (0.1-10).
  • the composite nicotine salt formulation is in the form of a composite nicotine salt formulation solution, and the mass concentration of nicotine in the composite nicotine salt formulation solution is 1%-70%.
  • the present application also provides a method for preparing the composite nicotine salt formulation, comprising the following steps:
  • the nicotine, organic acid, additive and carrier solvent are mixed and then heated and stirred to obtain the product.
  • the organic acid, additives and carrier solvent are mixed, heated and stirred, cooled, and then nicotine is added and stirred continuously to obtain the composite nicotine salt formulation.
  • the heating temperature is 40-70° C.
  • the heating stirring time is 1-10 min;
  • the present application does not specifically limit the method for adding nicotine.
  • nicotine can be added by dripping.
  • the present application also provides a use of the above-mentioned composite nicotine salt or the above-mentioned composite nicotine salt formulation in an atomization device.
  • the atomization device is an electronic cigarette.
  • the atomization core of the electronic cigarette is a ceramic atomization core.
  • the composite nicotine salt provided by the present application comprises raw materials including nicotine, organic acid and additives of specific structure. It has been found through research that nicotine is prone to degradation due to the molecular structure characteristics of nicotine itself, and the degradation products mainly include mysamine, cotinine, nicotine diene, etc., which will form soot on the surface of the electronic cigarette heating element. When the soot accumulates to a certain extent, it will cause smoking odor and reduce the sensory experience.
  • the present application adds additives of specific structure to the nicotine salt and combines it with nicotine to effectively slow down the degradation of nicotine, reduce the degree of soot formation, and improve the problem of smoking odor and reduced sensory experience caused by soot.
  • the composite nicotine salt provided by the present application is selected from at least one of catechin, epicatechin, gallocatechin, and epigallocatechin.
  • the present application adds the above additive to the nicotine salt and combines it with nicotine to effectively slow down the degradation of nicotine, reduce the degree of soot formation, and improve the problem of smoking odor and decreased sensory experience caused by soot.
  • FIG. 1 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Example 1 of the present application;
  • FIG2 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Example 5 of the present application;
  • FIG3 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Example 9 of the present application;
  • FIG4 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Example 13 of the present application;
  • FIG5 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Comparative Example 1 of the present application;
  • FIG6 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Comparative Example 2 of the present application;
  • FIG. 7 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Comparative Example 3 of the present application;
  • FIG8 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Comparative Example 4 of the present application;
  • FIG. 9 is a picture of the soot on the heating element after smoking the nicotine salt formulation obtained in Comparative Example 5 of the present application.
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This embodiment provides a method for preparing a composite nicotine salt formulation, comprising the following steps:
  • This comparative example provides a method for preparing a nicotine salt formulation, comprising the following steps:
  • This comparative example provides a method for preparing a nicotine salt formulation, comprising the following steps:
  • This comparative example provides a method for preparing a nicotine salt formulation, comprising the following steps:
  • This comparative example provides a method for preparing a nicotine salt formulation, comprising the following steps:
  • This comparative example provides a method for preparing a nicotine salt formulation, comprising the following steps:
  • the nicotine salt formulations prepared in the above-mentioned Examples 1, 5, 9, 13 and Comparative Examples 1-5 were smoked 200 times (smoked for 3 seconds and then stopped for 8 seconds) on the RELX 5th generation ceramic core to compare the accumulation of soot on the heating element.
  • the results are shown in Figures 1-9.
  • the soot accumulation of the nicotine salt formulation after adding the additives of the present application is significantly lighter than that of the comparative examples without the additives.
  • the use of the specific additives of the present application can significantly improve the accumulation of soot compared with other additives.
  • the nicotine salt formulations prepared in each embodiment and comparative example were placed in brown bottles and placed at room temperature for 2 weeks, 4 weeks, 8 weeks, and 16 weeks. Then, a small amount of nicotine salt formulation samples prepared in the above embodiments and comparative examples were taken at the start time, 2 weeks, 4 weeks, 8 weeks, and 16 weeks, and the content of the trace impurity mysamine therein was detected by GCMS method. The detailed results are shown in Table 1.
  • Table 1 shows that the longer the storage time, the higher the myosamine content in the nicotine salt formulation.
  • the increase in myosamine content in the nicotine formulation with the additive of the present application is significantly smaller than that in the nicotine formulation without the additive of the present application.
  • the specific additive of the present application can effectively inhibit the degradation of nicotine into myosamine and reduce the degree of soot formation.
  • Each embodiment and comparative example was placed in a brown bottle and placed at room temperature for 2 weeks, 4 weeks, 8 weeks, and 16 weeks. Then, a small amount of the nicotine salt formulation prepared in the above embodiments and comparative examples was taken at the start time, 2 weeks, 4 weeks, 8 weeks, and 16 weeks, respectively, and it was prepared into an atomized liquid with a nicotine content of 2% with PG and VG (PG/VG volume ratio of 7:3), and added to the same electronic cigarette device.
  • PG and VG PG/VG volume ratio of 7:3
  • Table 2 The evaluation results are shown in Table 2.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Toxicology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

本申请涉及电子烟技术领域,具体涉及一种复合烟碱盐、复合烟碱盐调配物及其制备方法和应用。本申请提供的复合烟碱盐,形成所述复合烟碱盐的原料包括烟碱、有机酸以及添加剂,所述添加剂具有如下所示的结构:。本申请提供的复合烟碱盐可有效减缓烟碱降解,降低烟垢生成程度,改善由于烟垢所造成的抽吸异味,感官体验下降的问题。

Description

复合烟碱盐、复合烟碱盐调配物及其制备方法和应用 技术领域
本申请涉及电子烟技术领域,具体涉及一种复合烟碱盐、复合烟碱盐调配物及其制备方法和应用。
背景技术
电子烟又名虚拟香烟、电子雾化器,电子烟具有与香烟相似的外观和味道,但一般不含香烟中的焦油、悬浮微粒等其他有害成分。目前电子烟大多采用烟碱盐作为有效成分。烟碱及烟碱盐调配物是所有烟草制品最重要的解瘾成分,近年来随着新型烟草电子烟的兴起,关于烟碱盐调配物的工艺和质量研究一直属于热点研究领域。
目前烟碱盐已普遍应用于电子烟油中,但仍存在一些问题,其中一个主要问题是含有烟碱盐的电子烟在经过长时间抽吸后会在电子烟发热体表面形成烟垢,而烟垢量累积到一定程度会造成抽吸异味,感官体验下降并提高了安全风险。因此如何降低烟垢的产生一直是电子烟烟碱盐研究的重点关注方向。
发明内容
本申请的目的在于克服现有电子烟烟碱盐在经过长时间抽吸后会在电子烟发热体表面形成烟垢,进而会造成抽吸异味,感官体验下降的缺陷,进而提供一种复合烟碱盐、复合烟碱盐调配物及其制备方法和应用。
为达到上述目的,本申请采用如下技术方案:
一种复合烟碱盐,形成所述复合烟碱盐的原料包括烟碱、有机酸以及添加剂,所述添加剂具有如下所示的结构:
Figure PCTCN2022128217-appb-000001
其中,
R 1-R 3各自独立的选自氢、羟基,且R 1-R 3中至少有两个取代基为羟基;
R 4-R 7各自独立的选自氢、羟基,且R 4-R 7中至少有两个取代基为羟基;
*表示碳手性中心。
可选的,R 1、R 3、R 5、R 6为羟基,R 2、R 7为氢,R 4为氢或羟基。
可选的,R 1、R 3、R 4、R 5、R 6为羟基,R 2、R 7为氢。
可选的,R 1、R 3、R 5、R 6为羟基,R 2、R 4、R 7为氢。
可选的,*处碳手性中心的立体构型各自独立的为R构型或S构型。
可选的,所述添加剂选自儿茶素、表儿茶素、没食子儿茶素、表没食子儿茶素中的至少一种。
可选的,所述有机酸选自脂肪族有机酸和/或芳香族有机酸。
可选的,所述脂肪族有机酸选自C1-C10脂肪族有机羧酸;所述芳香族有机酸选自C6-C14脂肪族有机羧酸;可选的,所述脂肪族有机酸选自C1-C5脂肪族有机羧酸;所述芳香族有机酸选自C6-C8脂肪族有机羧酸,可选的,所述C1-C5脂肪族有机羧酸中含有1-2个羧基,所述C6-C8脂肪族有机羧酸中含有1-2个羧基。
可选的,所述有机酸选自苯甲酸、苹果酸、乙酰丙酸、乳酸中的至少一种。
可选的,所述添加剂与烟碱的质量比为(0.01-5):100;
以羧酸根计的有机酸的摩尔用量与烟碱的摩尔用量之比为(0.5-2):1。
本申请还提供一种复合烟碱盐调配物,包括上述所述的复合烟碱盐。
可选的,所述复合烟碱盐调配物还包括载体溶剂。
可选的,所述载体溶剂选自C1-C10脂肪醇,所述脂肪醇中含有1-3个羟基,可选的,所述载体溶剂选自C1-C5脂肪醇,所述脂肪醇中含有1-3个羟基,可选的,所述载体溶剂包括丙二醇(PG)和/或蔬菜甘油(VG)。当载体溶剂为丙二醇和蔬菜甘油时,本申请不对二者的配比做具体限定,可选的,丙二醇和蔬菜甘油的体积比为(0.1-10):(0.1-10)。
可选的,所述复合烟碱盐调配物以复合烟碱盐调配物溶液的形式存在,所述复合烟碱盐调配物溶液中烟碱的质量浓度为1%-70%。
本申请还提供一种上述所述复合烟碱盐调配物的制备方法,包括如下步骤:
将烟碱、有机酸、添加剂和载体溶剂混合后加热搅拌即得。
可选的,将有机酸、添加剂和载体溶剂混合后进行加热搅拌,冷却,然后加入烟碱继续搅拌,得到所述复合烟碱盐调配物。
可选的,所述加热温度为40-70℃,加热搅拌时间为1-10min;
冷却温度至0-30℃,继续搅拌时间为5-1200min。
本申请不对烟碱的加入方式做具体限定,可选的,烟碱可采用滴加的方式加入。
本申请还提供一种上述所述的复合烟碱盐或上述所述的复合烟碱盐调配物在雾化装置中的应用。
可选的,所述雾化装置为电子烟。
可选的,所述电子烟的雾化芯为陶瓷雾化芯。
本申请的有益效果:
1、本申请提供的复合烟碱盐,形成所述复合烟碱盐的原料包括烟碱、有机酸以及特定结构的添加剂,经研究发现,由于烟碱本身分子结构特点易发生降解,降解产物主要包括麦斯明,可替宁,二烯烟碱等,其会在电子烟发热体表面形成烟垢,而烟垢量累积到一定程度会造成抽吸异味,感官体验下降,本申请通过在烟碱盐中加入特定结构的添加剂,利用其与烟碱进行结合,可有效减缓烟碱降解,降低烟垢生成程度,改善由于烟垢所造成的抽吸异味,感官体验下降的问题。
2、本申请提供的复合烟碱盐,进一步的,所述添加剂选自儿茶素、表儿茶素、没食子儿茶素、表没食子儿茶素中的至少一种。本申请通过在烟碱盐中加入上述添加剂,利用其与烟碱进行结合,可有效减缓烟碱降解,降低烟垢生成程度,改善由于烟垢所造成的抽吸异味,感官体验下降的问题。
附图说明
为了更清楚地说明本申请具体实施方式或现有技术中的技术方案,下面将对具体实施方式或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图是本申请的一些实施方式,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1是采用本申请实施例1获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图2是采用本申请实施例5获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图3是采用本申请实施例9获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图4是采用本申请实施例13获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图5是采用本申请对比例1获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图6是采用本申请对比例2获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图7是采用本申请对比例3获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图8是采用本申请对比例4获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片;
图9是采用本申请对比例5获得的烟碱盐调配物进行抽吸后发热体上的烟垢图片。
具体实施方式
提供下述实施例是为了更好地进一步理解本申请,并不局限于所述最佳实施方式,不对本申请的内容和保护范围构成限制,任何人在本申请的启示下或是将本申请与其他现有技术的特征进行组合而得出的任何与本申请相同或相近似的产品,均落在本申请的保护范围之内。
实施例中未注明具体实验步骤或条件者,按照本领域内的文献所描述的常规实验步骤的操作或条件即可进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规试剂产品。
实施例1
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.99g苯甲酸,0.02g表儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例2
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.99g苯甲酸,0.02g儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比4:7),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例3
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.99g苯甲酸,0.01g没食子儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比1:1),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例4
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.99g苯甲酸,0.01g表没食子儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比6:4),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例5
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.85g乙酰丙酸,0.01g儿茶素添加至具塞烧瓶中,加入3.13g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例6
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.85g乙酰丙酸,0.01g表儿茶素添加至具塞烧瓶中,加入3.13g PG和VG混合溶剂(PG和VG体积比4:6),然后在60℃下搅拌3min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌30min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例7
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.85g乙酰丙酸,0.01g没食子儿茶素添加至具塞烧瓶中,加入3.13g PG和VG混合溶剂(PG和VG体积比4:6),然后在40℃下搅拌10min直至完全溶解,冷却至10℃后将1g烟碱缓慢滴入上述溶液中,在10℃下将混合物搅拌100min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例8
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.85g乙酰丙酸,0.01g表没食子儿茶素添加至具塞烧瓶中,加入3.13g PG和VG混合溶剂(PG和VG体积比4:6),然后在70℃下搅拌1min直至完全溶解,冷却至5℃后将1g烟碱缓慢滴入上述溶液中,在5℃下将混合物搅拌1000min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例9
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.65g乳酸,0.01g儿茶素添加至具塞烧瓶中,加入3.36g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例10
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.65g乳酸,0.01g表儿茶素添加至具塞烧瓶中,加入3.36g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例11
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.65g乳酸,0.01g没食子儿茶素添加至具塞烧瓶中,加入3.36g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例12
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.65g乳酸,0.01g表没食子儿茶素添加至具塞烧瓶中,加入3.36g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例13
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.55g苹果酸,0.01g儿茶素添加至具塞烧瓶中,加入3.44g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例14
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.55g苹果酸,0.01g表儿茶素添加至具塞烧瓶中,加入3.44g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例15
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.55g苹果酸,0.01g没食子儿茶素添加至具塞烧瓶中,加入3.44g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例16
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.55g苹果酸,0.01g表没食子儿茶素添加至具塞烧瓶中,加入3.44g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例17
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将0.57g苯甲酸,0.05g表儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
实施例18
本实施例提供一种复合烟碱盐调配物的制备方法,包括如下步骤:
将1.46g苯甲酸,0.0001g表儿茶素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述复合烟碱盐调配物。
对比例1
本对比例提供一种烟碱盐调配物的制备方法,包括如下步骤:
将1g苯甲酸添加至具塞烧瓶中,加入3.00g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述烟碱盐调配物。
对比例2
本对比例提供一种烟碱盐调配物的制备方法,包括如下步骤:
将0.86g乙酰丙酸添加至具塞烧瓶中,加入3.13g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述烟碱盐调配物。
对比例3
本对比例提供一种烟碱盐调配物的制备方法,包括如下步骤:
将0.66g乳酸添加至具塞烧瓶中,加入3.36g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述烟碱盐调配物。
对比例4
本对比例提供一种烟碱盐调配物的制备方法,包括如下步骤:
将0.56g苹果酸添加至具塞烧瓶中,加入3.44g PG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述烟碱盐调配物。
对比例5
本对比例提供一种烟碱盐调配物的制备方法,包括如下步骤:
将0.99g苯甲酸,0.02g花青素添加至具塞烧瓶中,加入3.0gPG和VG混合溶剂(PG和VG体积比4:6),然后在50℃下搅拌5min直至完全溶解,冷却至20℃后将1g烟碱缓慢滴入上述溶液中,在20℃下将混合物搅拌15min,冷却至室温后密封储存即得所述烟碱盐调配物。
测试项目1
分别将上述实施例1,实施例5,实施例9,实施例13以及对比例1-5制备获得的烟碱盐调配物在悦刻5代陶瓷芯上机抽200口(抽3s然后停8s)后对比发热体上烟垢 积聚情况,结果见图1-9。由图1-4和图5-9显示,添加本申请添加剂后烟碱盐调配物烟垢积聚情况明显轻于未添加添加剂的各对比例。由图1和图9显示,采用本申请特定添加剂相比于其它添加剂,可明显改善垢积聚情况。
测试项目2
将各实施例和对比例制备得到的烟碱盐调配物分别装于棕色瓶中放置于室温环境下2周,4周,8周,16周。然后分别于开始时间,2周,4周,8周,16周时取少许上述实施例和对比例中制备的烟碱盐调配物样品,采用GCMS法检测其中微量杂质麦斯明含量,详细结果见表1。
表1
Figure PCTCN2022128217-appb-000002
表1显示,放置时间越长,烟碱盐调配物中麦斯明含量有不同程度上升,其中添加本申请添加剂的烟碱调配物麦斯明含量上升幅度明显小于未添加本申请添加剂的各烟碱调配物,本申请特定的添加剂可有效抑制烟碱降解为麦斯明,同时降低烟垢生成程度。
测试项目3
将各实施例和对比例分别装于棕色瓶中放置于室温环境下2周,4周,8周,16周。然后分别于开始时间,2周,4周,8周,16周时取少许上述实施例和对比例中制备的烟碱盐调配物,将其用PG和VG(PG/VG体积比为7:3)配制成烟碱含量2%的雾化液,添加到相同的电子烟装置中,由20名电子烟感官评价专家评价员对雾化液进行异味效果评价,每人一份感官质量评价表,采用暗评的评分方式,对烟碱雾化液进行抽吸,抽吸方法为:共抽吸3口,每口抽吸时间3s,抽吸间隔时间为5s。
依据异味感官效果评价指标进行打分评价。其中10分表示无异味,即所有评价员均感受不到异味,整体感官舒适愉悦,烟碱雾化液能被所有评价员接受;7-9表示较轻度异味,即个别评价专家(1-5名)感受到有轻微异味,烟碱雾化液能被大部分评价员接受;4-6表示轻度异味,即半数评价员能感受到异味,添加风味后可以掩盖;1-3表示中度异味,即大部分评价员都能感觉到异味,添加风味后仍不能掩盖,评价结果见表2。
表2
Figure PCTCN2022128217-appb-000003
Figure PCTCN2022128217-appb-000004
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本申请创造的保护范围之中。

Claims (20)

  1. 一种复合烟碱盐,其特征在于,形成所述复合烟碱盐的原料包括烟碱、有机酸以及添加剂,所述添加剂具有如下所示的结构:
    Figure PCTCN2022128217-appb-100001
    其中,
    R 1-R 3各自独立的选自氢、羟基,且R 1-R 3中至少有两个取代基为羟基;
    R 4-R 7各自独立的选自氢、羟基,且R 4-R 7中至少有两个取代基为羟基;
    *表示碳手性中心。
  2. 根据权利要求1所述的复合烟碱盐,其特征在于,R 1、R 3、R 5、R 6为羟基,R 2、R 7为氢,R 4为氢或羟基。
  3. 根据权利要求1或2所述的复合烟碱盐,其特征在于,R 1、R 3、R 4、R 5、R 6为羟基,R 2、R 7为氢。
  4. 根据权利要求1或2所述的复合烟碱盐,其特征在于,R 1、R 3、R 5、R 6为羟基,R 2、R 4、R 7为氢。
  5. 根据权利要求1-4任一项所述的复合烟碱盐,其特征在于,*处碳手性中心的立体构型各自独立的为R构型或S构型。
  6. 根据权利要求1-5任一项所述的复合烟碱盐,其特征在于,所述添加剂选自儿茶素、表儿茶素、没食子儿茶素、表没食子儿茶素中的至少一种。
  7. 根据权利要求1-6任一项所述的复合烟碱盐,其特征在于,所述有机酸选自脂肪族有机酸和/或芳香族有机酸。
  8. 根据权利要求7所述的复合烟碱盐,其特征在于,所述脂肪族有机酸选自C1-C10脂肪族有机羧酸;所述芳香族有机酸选自C6-C14脂肪族有机羧酸;可选的,所述脂肪族有机酸选自C1-C5脂肪族有机羧酸;所述芳香族有机酸选自C6-C8脂肪族有机羧酸,可选的,所述C1-C5脂肪族有机羧酸中含有1-2个羧基,所述C6-C8脂肪族有机羧酸中 含有1-2个羧基。
  9. 根据权利要求1-8任一项所述的复合烟碱盐,其特征在于,所述有机酸选自苯甲酸、苹果酸、乙酰丙酸、乳酸中的至少一种。
  10. 根据权利要求1-9任一项所述的复合烟碱盐,其特征在于,所述添加剂与烟碱的质量比为(0.01-5):100;
    以羧酸根计的有机酸的摩尔用量与烟碱的摩尔用量之比为(0.5-2):1。
  11. 一种复合烟碱盐调配物,其特征在于,包括权利要求1-10任一项所述的复合烟碱盐。
  12. 根据权利要求11所述的复合烟碱盐调配物,其特征在于,所述复合烟碱盐调配物还包括载体溶剂。
  13. 根据权利要求12所述的复合烟碱盐调配物,其特征在于,所述载体溶剂选自C1-C10脂肪醇,所述脂肪醇中含有1-3个羟基,可选的,所述载体溶剂选自C1-C5脂肪醇,所述脂肪醇中含有1-3个羟基,可选的,所述载体溶剂包括丙二醇和/或蔬菜甘油。
  14. 根据权利要求11-13任一项所述的复合烟碱盐调配物,其特征在于,所述复合烟碱盐调配物以复合烟碱盐调配物溶液的形式存在,所述复合烟碱盐调配物溶液中烟碱的质量浓度为1%-70%。
  15. 权利要求11-14任一项所述复合烟碱盐调配物的制备方法,其特征在于,包括如下步骤:
    将烟碱、有机酸、添加剂和载体溶剂混合后加热搅拌即得。
  16. 根据权利要求15所述复合烟碱盐调配物的制备方法,其特征在于,将有机酸、添加剂和载体溶剂混合后进行加热搅拌,冷却,然后加入烟碱继续搅拌,得到所述复合烟碱盐调配物。
  17. 根据权利要求16所述的制备方法,其特征在于,所述加热温度为40-70℃,加热搅拌时间为1-10min;
    冷却温度至0-30℃,继续搅拌时间为5-1200min。
  18. 权利要求1-10任一项所述的复合烟碱盐或权利要求11-14任一项所述的复合烟碱盐调配物在雾化装置中的应用。
  19. 根据权利要求18所述的应用,其特征在于,所述雾化装置为电子烟。
  20. 根据权利要求19所述的应用,其特征在于,所述电子烟的雾化芯为陶瓷雾化芯。
PCT/CN2022/128217 2022-10-28 2022-10-28 复合烟碱盐、复合烟碱盐调配物及其制备方法和应用 WO2024087160A1 (zh)

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