技术领域technical field
本发明属于烟草和烟用添加剂领域，涉及一种降低卷烟烟气中苯酚含量的方法。The invention belongs to the field of tobacco and tobacco additives, and relates to a method for reducing phenol content in cigarette smoke.
背景技术Background technique
卷烟烟气中的苯酚主要来源为糖类物质热分解及芸香苷和绿原酸等多酚类化合物裂解产生，被列在Hoffman 1990年发表的卷烟烟气中43种有害物的名单中。卷烟烟气中的酚类化合物是一种细胞原浆毒，作用机理是与细胞中的蛋白质发生化学反应，使蛋白质变性，进一步导致细胞失去活性。此外，烟气中的酚类物质中会产生酚醛味、涩味等单调的吃味、气味和药物灼烧感以及令人不愉快、沉闷的吸味，给烟气增加特殊味道，增加香味的复杂性，引起涩味、辣味、余味不干净等，从而影响卷烟制品的口感及抽吸品质。因此，采用合适的手段有效降低或去除卷烟主流烟气中的苯酚，可以提高卷烟制品的安全性。The main source of phenol in cigarette smoke is the pyrolysis of sugars and the cracking of polyphenolic compounds such as rutin and chlorogenic acid. It was listed in the list of 43 harmful substances in cigarette smoke published by Hoffman in 1990. The phenolic compound in cigarette smoke is a kind of cell protoplasm poison. The mechanism of action is to chemically react with the protein in the cell, denature the protein, and further cause the cell to lose its activity. In addition, the phenolic substances in the smoke will produce monotonous tastes such as phenolic and astringent tastes, odors and drug burning sensations, as well as unpleasant and dull smoking tastes, which will add special flavors to the smoke and increase the complexity of the aroma. Sex, causing astringency, spicy taste, unclean aftertaste, etc., thus affecting the taste and smoking quality of cigarette products. Therefore, adopting appropriate means to effectively reduce or remove phenol in mainstream cigarette smoke can improve the safety of cigarette products.
卷烟滤嘴大多数为单一的醋酸纤维一元滤棒，无法较好地吸附卷烟烟气中的苯酚，目前也有在滤棒中添加一些功能性材料来提高吸附的效果，如湖南中烟工业有限责任公司公开了一种在纤维基材内添加β-环糊精-g-乳酸共聚物活性材料颗粒能减少烟气中苯酚10.2％－35.1％的方法(CN102987564A)。该类技术虽然能选择性降低主流烟气中苯酚，但是该材料的制备过程较复杂，二元滤棒复合成本高，实验的重现性和稳定性较差，工业化可能性较小。Most of the cigarette filters are single cellulose acetate filter rods, which cannot absorb phenol in cigarette smoke well. At present, some functional materials are added to the filter rods to improve the adsorption effect, such as Hunan China Tobacco Industry Co., Ltd. The company discloses a method in which adding β-cyclodextrin-g-lactic acid copolymer active material particles into the fiber substrate can reduce phenol in smoke by 10.2%-35.1% (CN102987564A). Although this type of technology can selectively reduce phenol in mainstream smoke, the preparation process of this material is relatively complicated, the cost of binary filter rod compounding is high, the reproducibility and stability of the experiment are poor, and the possibility of industrialization is small.
目前，尚需要看法新的降低烟气中苯酚的工艺，并且为了尽可能保持烟支原有吸味，最好不会显著降低焦油量。At present, a new process for reducing phenol in smoke still needs to be seen, and in order to keep the original taste of cigarettes as much as possible, it is best not to significantly reduce the amount of tar.
发明内容Contents of the invention
本发明人经过深入的研究和创造性的劳动，惊奇地发现，苦瓜皂苷(或者含有苦瓜皂苷的苦瓜提取物)能够有效地降低卷烟烟气中苯酚的含量，焦油量变化不大，并且不改变烟支原有吸味。由此提供了下述发明：After in-depth research and creative work, the inventors have surprisingly found that Momordica saponin (or bitter melon extract containing Momordica saponin) can effectively reduce the content of phenol in cigarette smoke, the amount of tar does not change much, and does not change the smoke content of cigarettes. Branches have a smell. The following inventions are thus provided:
本发明的一个方面涉及一种降低卷烟烟气中苯酚含量的方法，包括向滤棒和/或烟丝中添加苦瓜皂苷或含苦瓜皂苷的苦瓜提取物的步骤。One aspect of the present invention relates to a method for reducing phenol content in cigarette smoke, comprising the step of adding charantia saponin or bitter melon extract containing charantia saponin to a filter rod and/or shredded tobacco.
在本发明的一个实施方案中，所述的方法，其中，苦瓜皂苷或含苦瓜皂苷的苦瓜提取物的添加量按照每支卷烟或者每支滤棒中的苦瓜皂苷的量计算为1－150μg，优选为5－100μg或者10－50μg，更优选为15－30μg，例如15－25μg、15－20μg、20－30μg、20－25μg、15μg、20μg、25μg或30μg。In one embodiment of the present invention, the method, wherein the added amount of Momordica saponin or Momordica charantia saponin-containing extract is 1-150 μg calculated according to the amount of Momordica saponin in each cigarette or filter stick, It is preferably 5-100 μg or 10-50 μg, more preferably 15-30 μg, such as 15-25 μg, 15-20 μg, 20-30 μg, 20-25 μg, 15 μg, 20 μg, 25 μg or 30 μg.
在本发明的一个实施方案中，所述的方法，其中，将滤棒在苦瓜皂苷溶液或者含苦瓜皂苷的苦瓜提取物中浸泡；优选地，将浸泡后的滤棒晾干或者烘干。In one embodiment of the present invention, the method, wherein the filter stick is soaked in the bitter melon saponin solution or the bitter melon extract containing the bitter melon saponin; preferably, the soaked filter stick is air-dried or oven-dried.
在本发明的一个实施方案中，所述的方法，其中，苦瓜皂苷溶液为苦瓜皂苷的醇溶液；优选地，为苦瓜皂苷的乙醇溶液、正丁醇溶液或异戊醇溶液；优选地，所述苦瓜皂苷溶液的浓度为50－100mg/mL。In one embodiment of the present invention, described method, wherein, bitter melon saponin solution is the alcohol solution of bitter melon saponin; Preferably, it is the ethanol solution of bitter melon saponin, n-butanol solution or isoamyl alcohol solution; Preferably, the The concentration of the bitter melon saponin solution is 50-100 mg/mL.
在本发明的一个实施方案中，所述的方法，其中，所述浸泡的时间为至少5秒，优选为10－30秒。In one embodiment of the present invention, the method, wherein the soaking time is at least 5 seconds, preferably 10-30 seconds.
在本发明的一个实施方案中，所述的方法，其中，所述晾干或烘干的温度为25℃－35℃，时间为4－6小时。In one embodiment of the present invention, the method, wherein the drying or drying temperature is 25°C-35°C, and the time is 4-6 hours.
在本发明的一个实施方案中，所述的方法，其中，所述苦瓜皂苷为苦瓜皂苷A。In one embodiment of the present invention, the method, wherein the Momordica saponin is Momordica saponin A.
在本发明的一个实施方案中，所述的方法包括下述步骤：卷烟卷制前，将滤棒在一定浓度的苦瓜皂苷溶液中浸泡后，取出置于通风处中于一定的温度下晾干后使用。所述苦瓜皂苷溶液为浓度为50－100mg/mL苦瓜皂苷醇(优选为乙醇、正丁醇、异戊醇)溶液，所述浸泡时间为10－30秒，所述晾干温度为25℃－35℃，晾干时间为4－6小时。In one embodiment of the present invention, the method includes the following steps: before cigarette rolling, soak the filter stick in a certain concentration of bitter melon saponin solution, take it out and place it in a ventilated place to dry at a certain temperature used later. The bitter melon saponin solution is a solution of bitter melon saponin alcohol (preferably ethanol, n-butanol, isoamyl alcohol) with a concentration of 50-100 mg/mL, the soaking time is 10-30 seconds, and the drying temperature is 25°C- 35 ℃, drying time is 4-6 hours.
本发明的另一方面涉及一种烟草制品，其含有苦瓜皂苷或含苦瓜皂苷的苦瓜提取物；优选地，所述烟草制品为卷烟或者滤棒；优选地，苦瓜皂苷或含苦瓜皂苷的苦瓜提取物的含量按照每支卷烟或者每支滤棒中的苦瓜皂苷的量计算为1－150μg，优选为5－100μg或者10－50μg，更优选为15－30μg，例如15－25μg、15－20μg、20－30μg、20－25μg、15μg、20μg、25μg或30μg；优选地，所述苦瓜皂苷为苦瓜皂苷A。Another aspect of the present invention relates to a tobacco product, which contains Momordica saponin or a bitter melon extract containing Momordica saponin; preferably, the tobacco product is a cigarette or a filter stick; preferably, Momordica saponin or a bitter melon extract containing The content of the substance is 1-150 μg, preferably 5-100 μg or 10-50 μg, more preferably 15-30 μg, such as 15-25 μg, 15-20 μg, calculated according to the amount of bitter melon saponin in each cigarette or each filter stick. 20-30 μg, 20-25 μg, 15 μg, 20 μg, 25 μg or 30 μg; preferably, the Momordica saponin is Momordica saponin A.
本发明的再一方面涉及苦瓜皂苷或含苦瓜皂苷的苦瓜提取物在降低卷烟烟气中苯酚含量中的用途；优选地，所述苦瓜皂苷为苦瓜皂苷A。Another aspect of the present invention relates to the use of Momordica saponin or the extract of Momordica charantia containing Momordica saponin in reducing the phenol content in cigarette smoke; preferably, the saponin of Momordica charantia is Momordica charantia.
本发明的再一方面涉及一种烟用添加剂，其含有苦瓜皂苷或含苦瓜皂苷的苦瓜提取物；可选地，所述烟用添加剂还包含烟用溶剂例如乙醇、正丁醇或异戊醇；优选地，所述苦瓜皂苷为苦瓜皂苷A。Another aspect of the present invention relates to a tobacco additive, which contains Momordica charantia saponin or a bitter melon extract containing Momordica charantia saponin; optionally, the tobacco additive further includes a tobacco solvent such as ethanol, n-butanol or isoamyl alcohol ; Preferably, the Momordica saponin is Momordica saponin A.
本发明中，如果没有特别说明，所述“苦瓜”是指葫芦科苦瓜属植物苦瓜(Momordica charantia L.)的果实。果实中的种子可以去除何种不去除。In the present invention, unless otherwise specified, the "bitter melon" refers to the fruit of Momordica charantia L., a plant of the genus Momordica cucurbitaceae. The seeds in the fruit can be removed or not.
本发明中，术语“苦瓜皂苷”又称为苦瓜皂甙，主要由苦瓜皂甙A和苦瓜皂甙B组成。在本发明一个优选的实施方案中，所述苦瓜皂苷是指苦瓜皂甙A(CAS号81910-41-0)。In the present invention, the term "Mosantia saponin" is also called Momordica saponin, which mainly consists of Momordica saponin A and Momordica saponin B. In a preferred embodiment of the present invention, said Momordica saponin refers to Momordica saponin A (CAS No. 81910-41-0).
发明的有益效果Beneficial Effects of the Invention
本发明能够实现下述技术效果中一种或多种：The present invention can realize one or more in the following technical effect:
(1)苦瓜皂苷能够卷烟主流烟气中苯酚，幅度达到20％以上(例如28％)，进而达到了降低卷烟危害性的目的。(1) Momordica saponin can reduce the phenol in the mainstream smoke of cigarettes by more than 20% (for example, 28%), thereby achieving the purpose of reducing the harmfulness of cigarettes.
(2)添加苦瓜皂苷(或者含有苦瓜皂苷的苦瓜提取物)不改变烟支原有吸味。不拘于理论的限制，可能是由于苦瓜皂苷的空间结构大，对焦油的阻隔小。(2) Adding balsam pear saponin (or balsam pear extract containing balsam pear saponin) does not change the original taste of cigarettes. Without being limited by theory, it may be due to the large spatial structure of Momordica saponin and the small barrier to tar oil.
(3)本领域技术人员知悉，如果焦油量降低的话，烟气劲头下降，吸味改变。本发明人惊奇地发现，本发明在降低苯酚的同时，却对烟气中的焦油量影响不大，有利于保持卷烟的口感和香气。(3) Those skilled in the art know that if the amount of tar is reduced, the strength of the smoke will decrease and the taste will change. The inventor surprisingly found that the present invention has little effect on the amount of tar in smoke while reducing phenol, which is beneficial to maintaining the taste and aroma of cigarettes.
(4)苦瓜皂苷微苦，使滤棒具有独特的生津感，给消费者带来不同的吸食体验。(4) Bitter melon saponins give the filter stick a unique feeling of invigorating body fluids and bring different smoking experiences to consumers.
(5)制作成本低、操作简单、稳定性好，解决了原有技术二元滤棒复合成本高，实验的重现性和稳定性较差，工业化可能性较小等弊端。(5) The production cost is low, the operation is simple, and the stability is good, which solves the disadvantages of the original technology, such as high compounding cost of the binary filter rod, poor reproducibility and stability of the experiment, and low possibility of industrialization.
具体实施方式detailed description
下面将结合实施例对本发明的实施方案进行详细描述，但是本领域技术人员将会理解，下列实施例仅用于说明本发明，而不应视为限定本发明的范围。实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。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产品。Embodiments of the present invention will be described in detail below in conjunction with examples, but those skilled in the art will understand that the following examples are only for illustrating the present invention, and should not be considered as limiting the scope of the present invention. Those who do not indicate the specific conditions in the examples are carried out according to the conventional conditions or the conditions suggested by the manufacturer. The reagents or instruments used were not indicated by the manufacturer, and they were all commercially available conventional products.
下面的实施例中，如果没有特别说明，所用的苦瓜皂苷均为苦瓜皂苷A，购自上海宏顺生物科技有限公司，CAS号81910-41-0。In the following examples, unless otherwise specified, the used Momordica saponin is Momordica saponin A, purchased from Shanghai Hongshun Biotechnology Co., Ltd., CAS No. 81910-41-0.
实施例1：苯酚含量和焦油量的测定(1)Embodiment 1: the mensuration of phenol content and tar amount (1)
牌号1卷烟样品卷制前，将滤棒在50mg/mL苦瓜皂苷乙醇溶液中浸泡30秒后，取出置于通风处中于25℃下晾6小时后使用。与未经处理样品进行卷烟机模拟抽吸，对烟气中苯酚的含量进行检测。Before rolling the brand 1 cigarette sample, soak the filter stick in 50 mg/mL Momordica saponin ethanol solution for 30 seconds, take it out and place it in a ventilated place to dry at 25°C for 6 hours before use. Simulated cigarette smoking with untreated samples was carried out to detect the content of phenol in the smoke.
苯酚的测定按照下面的文献进行：刘芳等，超声萃取－快速HPLC法测定卷烟主流烟气中的苯酚、甲酚和苯二酚，烟草科技，2007年第10期(总第243期)，p31－35。The determination of phenol is carried out according to the following literature: Liu Fang et al., Determination of phenol, cresol and hydroquinone in mainstream cigarette smoke by ultrasonic extraction-fast HPLC method, Tobacco Science and Technology, 2007, No. 10 (Total No. 243), p31-35.
焦油量的测定按照GB/T 19609进行。The determination of the amount of tar is carried out according to GB/T 19609.
实验结果如下面的表1所示。The experimental results are shown in Table 1 below.
表1：选择性降苯酚的效果比较Table 1: Comparison of the effects of selective phenol reduction
结果表明，苦瓜皂苷能够有效地降低烟气中苯酚的含量，降幅达20％以上。焦油量变化不大。The results show that bitter melon saponin can effectively reduce the content of phenol in smoke, and the reduction rate reaches more than 20%. The amount of tar did not change much.
实施例2：苯酚含量和焦油量的测定(2)Embodiment 2: the mensuration of phenol content and tar amount (2)
牌号2卷烟样品卷制前，将滤棒在75mg/mL苦瓜皂苷正丁醇溶液中浸泡20秒后，取出置于通风处中于30℃下晾5小时后使用。与未经处理样品进行卷烟机模拟抽吸，按照与实施例1相同的方法对烟气中苯酚含量和焦油量进行检测。Before rolling the brand 2 cigarette sample, soak the filter stick in 75 mg/mL bitter melon saponin n-butanol solution for 20 seconds, take it out and place it in a ventilated place to dry at 30°C for 5 hours before use. Simulated smoking with a cigarette machine was carried out with the untreated sample, and the phenol content and tar amount in the smoke were detected by the same method as in Example 1.
结果如下面的表2所示。The results are shown in Table 2 below.
表2：选择性降苯酚的效果比较Table 2: Comparison of the effects of selective phenol reduction
结果表明，苦瓜皂苷能够有效地降低烟气中苯酚的含量，降幅达20％以上。焦油量变化不大。The results show that bitter melon saponin can effectively reduce the content of phenol in smoke, and the reduction rate reaches more than 20%. The amount of tar did not change much.
实施例3：苯酚含量和焦油量的测定(3)Embodiment 3: the mensuration of phenol content and tar amount (3)
牌号3卷烟样品卷制前，将滤棒在100mg/mL苦瓜皂苷醇异戊醇溶液中浸泡10秒后，取出置于通风处中于35℃下晾4小时后使用。与未经处理样品进行卷烟机模拟抽吸，按照与实施例1相同的方法对烟气中苯酚含量和焦油量进行检测。Before rolling the brand 3 cigarette sample, soak the filter stick in 100 mg/mL bitter melon saponin alcohol isoamyl alcohol solution for 10 seconds, take it out and place it in a ventilated place to dry at 35°C for 4 hours before use. Simulated smoking with a cigarette machine was carried out with the untreated sample, and the phenol content and tar amount in the smoke were detected by the same method as in Example 1.
结果如下面的表3所示。The results are shown in Table 3 below.
表3：选择性降苯酚的效果比较Table 3: Comparison of the effects of selective phenol reduction
结果表明，苦瓜皂苷能够有效地降低烟气中苯酚的含量，降幅达20％以上。焦油量变化不大。The results show that bitter melon saponin can effectively reduce the content of phenol in smoke, and the reduction rate reaches more than 20%. The amount of tar did not change much.
实施例4：滤棒中苦瓜皂苷添加量的测定Embodiment 4: the mensuration of the addition amount of bitter melon saponin in the filter stick
测定实施例1－3中制得的卷烟样品滤棒中苦瓜皂苷的含量/添加量。测定方法按照如下参考文献进行：石雪萍等，HPLC—ELSD测定苦瓜皂甙的含量，天然产物研究与开发，Nat Prod Res Dev，2006，18：471-473。The content/addition amount of bitter melon saponins in the filter sticks of the cigarette samples prepared in Examples 1-3 was determined. The determination method was carried out according to the following references: Shi Xueping et al., HPLC-ELSD Determination of Momordica saponin content, Natural Product Research and Development, Nat Prod Res Dev, 2006, 18: 471-473.
结果测得实施例1－3中每支滤棒中的苦瓜皂苷含量分别为14.5μg，21.0μg，29.8μg。另外，不拘于理论的限制，由于不同的卷烟原本的苯酚和焦油含量均不相同，以及滤棒打孔、滤嘴通风度等因素的影响，导致在不同的卷烟中，苯酚降低程度不一定与苦瓜皂苷添加量呈正相关。Results The content of Momordica saponin in each filter stick in Examples 1-3 was measured to be 14.5 μg, 21.0 μg, and 29.8 μg, respectively. In addition, without being limited by theory, due to the different original phenol and tar contents of different cigarettes, as well as the influence of factors such as filter rod perforation and filter ventilation, the degree of phenol reduction in different cigarettes is not necessarily the same as that of The addition amount of bitter melon saponin was positively correlated.
实施例5：评吸实验Embodiment 5: Evaluation and suction experiment
1.评吸样品：实施例1－3制备的样品1－3，以及没有添加苦瓜皂苷的空白牌号1－3卷烟。1. Smoking samples: samples 1-3 prepared in Example 1-3, and blank brand 1-3 cigarettes without adding bitter melon saponin.
2.评吸方法：参照YC/T 497-2014卷烟中式卷烟风格感官评价方法进行评析。2. Smoking evaluation method: Refer to YC/T 497-2014 cigarette Chinese cigarette style sensory evaluation method for evaluation and analysis.
3.评吸结果：3. Evaluation results:
总体评价：添加后卷烟与添加前空白卷烟吸味相比均没有明显改变。添加后滤棒稍变硬，但是添加后滤棒略带苦味，生津感更好。Overall evaluation: There is no significant change in the smoking taste of the cigarettes after the addition compared with the blank cigarettes before the addition. After adding, the filter stick becomes slightly harder, but after adding, the filter stick has a slightly bitter taste, and the feeling of saliva is better.
尽管本发明的具体实施方式已经得到详细的描述，本领域技术人员将会理解。根据已经公开的所有教导，可以对那些细节进行各种修改和替换，这些改变均在本发明的保护范围之内。本发明的全部范围由所附权利要求及其任何等同物给出。Although specific embodiments of the present invention have been described in detail, those skilled in the art will understand. Based on all the teachings that have been disclosed, various modifications and substitutions can be made to those details, and these changes are all within the scope of the invention. The full scope of the invention is given by the appended claims and any equivalents thereof.
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| CN (1) | CN106263024A (en) |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106833893A (en)* | 2017-02-27 | 2017-06-13 | 河南中烟工业有限责任公司 | Milk fragrance additive of phenol and its preparation method and application in a kind of reduction cigarette smoke |
| CN113549639A (en)* | 2021-07-21 | 2021-10-26 | 云南中烟工业有限责任公司 | Regulatory gene for reducing content of total protein and smoke phenol in tobacco leaves |
| CN113893613A (en)* | 2021-09-28 | 2022-01-07 | 深圳市真味生物科技有限公司 | Filtering material convenient to replace, filtering device and heating non-combustion appliance |
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| CN1222388A (en)* | 1998-12-15 | 1999-07-14 | 王佐华 | Antidotal agent to eliminate tobacco toxin and its application |
| CN101138435A (en)* | 2007-09-30 | 2008-03-12 | 广西中烟工业公司 | A kind of natural acrylic fiber filter cigarette additive and preparation method thereof |
| CN101214090A (en)* | 2008-01-07 | 2008-07-09 | 红云烟草(集团)有限责任公司 | A kind of composite filter adsorption material and its preparation method and application |
| CN101390658A (en)* | 2008-11-07 | 2009-03-25 | 云南烟草科学研究院 | A composite cigarette filter containing plant saponin extract |
| CN101461514A (en)* | 2009-01-22 | 2009-06-24 | 韩金光 | Bitter melon extract and preparation method thereof |
| CN101803799A (en)* | 2010-04-16 | 2010-08-18 | 大百汇实业集团有限公司 | Gypenoside-contained cigarette and manufacture method thereof |
| CN102763899A (en)* | 2012-07-27 | 2012-11-07 | 红云红河烟草(集团)有限责任公司 | Application of bitter gourd in cigarette |
| CN104522880A (en)* | 2014-12-25 | 2015-04-22 | 鹰潭华宝香精香料有限公司 | Composite plant extract and preparation method thereof |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1222388A (en)* | 1998-12-15 | 1999-07-14 | 王佐华 | Antidotal agent to eliminate tobacco toxin and its application |
| CN101138435A (en)* | 2007-09-30 | 2008-03-12 | 广西中烟工业公司 | A kind of natural acrylic fiber filter cigarette additive and preparation method thereof |
| CN101214090A (en)* | 2008-01-07 | 2008-07-09 | 红云烟草(集团)有限责任公司 | A kind of composite filter adsorption material and its preparation method and application |
| CN101390658A (en)* | 2008-11-07 | 2009-03-25 | 云南烟草科学研究院 | A composite cigarette filter containing plant saponin extract |
| CN101461514A (en)* | 2009-01-22 | 2009-06-24 | 韩金光 | Bitter melon extract and preparation method thereof |
| CN101803799A (en)* | 2010-04-16 | 2010-08-18 | 大百汇实业集团有限公司 | Gypenoside-contained cigarette and manufacture method thereof |
| CN102763899A (en)* | 2012-07-27 | 2012-11-07 | 红云红河烟草(集团)有限责任公司 | Application of bitter gourd in cigarette |
| CN104522880A (en)* | 2014-12-25 | 2015-04-22 | 鹰潭华宝香精香料有限公司 | Composite plant extract and preparation method thereof |
| Title |
|---|
| 陶冶: "人参皂甙在卷烟中的应用", 《湖南文理学院学报（自然科学版）》* |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106833893A (en)* | 2017-02-27 | 2017-06-13 | 河南中烟工业有限责任公司 | Milk fragrance additive of phenol and its preparation method and application in a kind of reduction cigarette smoke |
| CN113549639A (en)* | 2021-07-21 | 2021-10-26 | 云南中烟工业有限责任公司 | Regulatory gene for reducing content of total protein and smoke phenol in tobacco leaves |
| CN113549639B (en)* | 2021-07-21 | 2022-07-29 | 云南中烟工业有限责任公司 | Regulatory gene for reducing contents of total proteins and phenol in flue gas of tobacco leaves |
| CN113893613A (en)* | 2021-09-28 | 2022-01-07 | 深圳市真味生物科技有限公司 | Filtering material convenient to replace, filtering device and heating non-combustion appliance |
| CN113893613B (en)* | 2021-09-28 | 2023-09-12 | 深圳市真味生物科技有限公司 | Filter material convenient to replace, filter device and heating non-combustion appliance |
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | Application publication date:20170104 | |
| RJ01 | Rejection of invention patent application after publication |