EP3834635B1 - Functional cigarette filter containing natural plant material, cigarette, and method for producing same - Google Patents
Functional cigarette filter containing natural plant material, cigarette, and method for producing same Download PDFInfo
- Publication number
- EP3834635B1 EP3834635B1 EP20851271.5A EP20851271A EP3834635B1 EP 3834635 B1 EP3834635 B1 EP 3834635B1 EP 20851271 A EP20851271 A EP 20851271A EP 3834635 B1 EP3834635 B1 EP 3834635B1
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- EP
- European Patent Office
- Prior art keywords
- natural plant
- cigarette
- filter
- rosemary
- granules
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
- A24D3/10—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent of cellulose or cellulose derivatives
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/061—Use of materials for tobacco smoke filters containing additives entrapped within capsules, sponge-like material or the like, for further release upon smoking
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D1/00—Cigars; Cigarettes
- A24D1/04—Cigars; Cigarettes with mouthpieces or filter-tips
- A24D1/042—Cigars; Cigarettes with mouthpieces or filter-tips with mouthpieces
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/02—Manufacture of tobacco smoke filters
- A24D3/0204—Preliminary operations before the filter rod forming process, e.g. crimping, blooming
- A24D3/0212—Applying additives to filter materials
- A24D3/0225—Applying additives to filter materials with solid additives, e.g. incorporation of a granular product
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/04—Tobacco smoke filters characterised by their shape or structure
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/04—Tobacco smoke filters characterised by their shape or structure
- A24D3/048—Tobacco smoke filters characterised by their shape or structure containing additives
Definitions
- the following description relates to a cigarette filter containing natural plant material that reduces cigarette-derived odor ingredient and intraoral halitosis inducing substance, and a cigarette including the filter and a preparation method thereof.
- the cigarette is one of the most popular preferences, and consumers get a sense of satisfaction using smoking the cigarette.
- research on adding natural plant material to cigarettes is being actively conducted so that consumers may feel the scent of natural plant material that suits their preferences simultaneously with smoking.
- cigarette odors that are left in the smoker's mouth or hands are perceived as negative by neighbors.
- research on cigarettes with less cigarette odor and preparation methods thereof is being actively conducted.
- the effect of reducing the intraoral halitosis ingredient may be identified as the volatile ingredient is delivered into the smoke under the chemical, antibacterial and masking actions of natural plant material-based volatile substances.
- gas molecules fly at a speed of 100 m/s to 1,000 m/s, and they collide with other molecules about at least 20,000 times during travel thereof by 1 mm, thereby to realize the above effect.
- the effect of reducing halitosis inducing ingredients derived from cigarettes may be expected using the chemistry and adsorption actions of non-volatile substances based on the natural plant material. Therefore, there is a need for a study on an optimized method to reduce cigarette-derived odor ingredient and intraoral halitosis inducing substance by applying natural plant material to a cigarette filter.
- CN106617285 A teaches a cigarette filter comprising natural plant based granules and hydroxypropyl methylcellulose (HPMC) in the ratio of 50:1. The ganules are made by granulation. A corresponding teaching as in CN106617285 A is also included in CN103689796 B , CN105167190 B , CN110013806 A , US2009246525 A1 , and US2011277781 A1 .
- a purpose of the present disclosure is to provide a cigarette filter as defined in claim 1 including natural plant based granules composed of a natural plant material and a binder; and a filter portion to accommodate therein the natural plant based granules, in which the binder is hydroxy propyl methyl cellulose (HPMC), and a weight ratio of the natural plant material and the binder is in a range of 95% to 99% : 5% to 1%.
- HPMC hydroxy propyl methyl cellulose
- Another purpose of the present disclosure is to provide a cigarette including the cigarette filter.
- Another purpose of the present disclosure is to provide a preparation method of a cigarette filter as defined in claim 8, the method including inserting a binder into a natural plant material to prepare natural plant based granules; drying and classifying the natural plant based granules; and adding the classified natural plant based granules to a cigarette filter, in which the binder is hydroxy propyl methyl cellulose (HPMC) of a viscosity of 50 cps, in which a weight ratio of the natural plant material and a binder is in a range of 95% to 99% : 5% to 1%.
- HPMC hydroxy propyl methyl cellulose
- a cigarette filter including natural plant based granules composed of a natural plant material and a binder; and a filter portion to accommodate therein the natural plant based granules, in which the binder is hydroxy propyl methyl cellulose (HPMC), and a weight ratio of the natural plant material and the binder is in a range of 95% to 99% : 5% to 1%.
- HPMC hydroxy propyl methyl cellulose
- the natural plant material may include at least one selected from rosemary, pine needle, peppermint, spearmint, coffee, pineapple, chamomile, orange, eucalyptus, thyme, geranium, jasmine, rosemary, lavender, lemongrass, pine needle, clover, sage, taxol, bergamot, basil, thyme, valerian, hyssop, tea tree, myrrh, and juniper.
- a hardness of the natural plant based granule may be in a range of 90.0% to 99.0%.
- a size of the natural plant based granule may be in a range of 0.25 mm to 2.0 mm.
- a moisture content of the natural plant based granule may be in a range of 5% to 12% of a total weight of the natural plant based granules.
- the cigarette filter may be a single filter or a multiple filter.
- the cigarette filter includes a herb oil capsule containing an oil ingredient extracted from the natural plant material.
- a cigarette including the cigarette filter.
- the cigarette may reduce methylmercaptan as a halitosis inducing ingredient.
- the cigarette may reduce a cigarette odor inducing ingredient including ammonia, acrolein, crotonaldehyde, methyl ethyl ketone (MEK), and 1,3-butadiene, acrylonitrile, benzene, and pyridine by 9% to 55%.
- a cigarette odor inducing ingredient including ammonia, acrolein, crotonaldehyde, methyl ethyl ketone (MEK), and 1,3-butadiene, acrylonitrile, benzene, and pyridine by 9% to 55%.
- a preparation method of a cigarette filter including inserting a binder into a natural plant material to prepare natural plant based granules; drying and classifying the natural plant based granules; and adding the classified natural plant based granules to a cigarette filter, in which in the preparing of the natural plant based granules, the binder is hydroxy propyl methyl cellulose (HPMC) of a viscosity of 50 cps, in which a weight ratio of the natural plant material and a binder is in a range of 95% to 99% : 5% to 1%.
- HPMC hydroxy propyl methyl cellulose
- the preparing of the natural plant based granules may include adding 2% of hydroxy propyl methyl cellulose (HPMC) of a viscosity of 50 cps as a binder to 50% ethanol to produce a binder solution, and mixing pulverized natural plant powders and the binder solution with each other to form a mixture and stirring the mixture, and shaping and classifying the mixture.
- HPMC hydroxy propyl methyl cellulose
- the drying of the natural plant based granules may include one of freeze-drying, hot air drying, warm air drying, and fluidized bed drying methods.
- a size of the classified natural plant based granule may be in a range of 0.25 mm to 2.0 mm.
- the adding of the classified natural plant based granules to the cigarette filter may include adding a herb extract to acetate tow using a spraying method or a nozzle based spraying method (TJNS).
- TJNS nozzle based spraying method
- the method of preparing the cigarette filter may further include injecting a herb oil capsule containing an oil ingredient extracted from the natural plant material into the cigarette filter using a capsule injection facility.
- an added amount of the granules may be in a range of 0.5 to 4 mg/mm Tip.
- the cigarette filter including the natural plant based granules absorbs, binds, and neutralizes the cigarette-derived odor ingredient or halitosis inducing ingredient, thus reducing the unique cigarette-derived odor and halitosis derived from a mouth of a cigarette smoker.
- the cigarette filter may further include the herb extract or the herb oil capsule, thereby to enhance the halitosis reduction effect, thus providing a cigarette that minimizes discomfort to non-smokers as well as smokers.
- the natural plant based granules may have a hardness of 90.0% to 99.0% and a moisture content of 5% to 12%. Due to the natural plant based granules having the above characteristics, activated carbon as a second additive applied to a cigarette filter may not be used. When applying the natural plant based granules to the cigarette filter, the filter productivity may be improved.
- the effect of the present disclosure is not limited to the above effect, and may include all effects that may be deduced from the detailed description of the present disclosure or a configuration of the invention described in the claims.
- a cigarette filter to which natural plant based granules are applied in order to reduce the cigarette-derived odor ingredient and intraoral halitosis inducing substance.
- a cigarette filter as defined in claim 1 including natural plant based granules composed of a natural plant material and a binder; and a filter portion to accommodate therein the natural plant based granules, in which the binder is hydroxy propyl methyl cellulose (HPMC), and a weight ratio of the natural plant material and the binder is in a range of 95 to 99% : 5 to 1%.
- HPMC hydroxy propyl methyl cellulose
- the present disclosure aims to provide a cigarette filter having granularized natural plant material added thereto to deliver a fresh and clean flavor evenly from the first sip to the last sip during smoking, and to neutralize and remove bad odors associated with smoking.
- the natural plant material may include at least one selected from rosemary, pine needle, peppermint, spearmint, coffee, pineapple, chamomile, orange, eucalyptus, thyme, geranium, jasmine, rosemary, lavender, lemongrass, pine needle, clover, sage, taxol, bergamot, basil, thyme, valerian, hyssop, tea tree, myrrh, and juniper.
- the present disclosure is not limited thereto.
- the natural plant materials processed in accordance with the present disclosure may be applied alone or in combination with each other as long as the plants are allowed under the Food Additives Act. Plant parts containing the largest amount of natural scent ingredients (for example, leaf, stem, root, fruit, etc.) may be used in a natural state or may be processed in a suitable manner for application to the cigarettes.
- pine needle and rosemary were selected as natural plant materials, and the ingredients and efficacy thereof were analyzed.
- Cigarette-derived halitosis ingredient reduction effect may be realized by chemical neutralization of volatile fragrance ingredients such as terpenes, chemical reactions of fragrance ingredients such as polyphenol, and physical adsorption by granule porous mass and dietary fiber.
- the effect of increasing the expression of natural plant flavor may be implemented via the volatilization of the volatile fragrance ingredients.
- the disclosure is not limited thereto.
- the binder is hydroxy propyl methyl cellulose (HPMC) which may be easily coupled to the natural plant material and allow the size and the hardness of natural plant based granules to be proper.
- HPMC binder with a viscosity of 50 cps is used.
- the content of the binder combined with the natural plant material is 1 to 5%, preferably 2%, so that the weight ratio of the natural plant material and the binder is 98% : 2%.
- extracts of various natural plants may be added thereto to improve the adsorption capacity.
- the alcohol concentration for extracting the extract may be 0 to 100%, preferably 50%.
- inorganic binders selected from silica, silicate and bentonite may be further added thereto in a weight ratio of 1 to 30% based on the natural plant material.
- the natural plant based granules are prepared as wet or dry granules which are added to the filter so that the natural plant scent may be uniformly carried from the beginning to the end during smoking.
- the natural plant based granules are preferably prepared as wet and dry granules, but may include extract, capsule, and mixture types.
- the size of each of the natural plant based granules may be 0.25 to 2.0 mm, preferably, 0.5 to 1.0 mm.
- the size of the prepared natural plant based granules is smaller than 0.25 mm, in the cigarette filter preparation, a scattering (flying) amount of granules increases, thus causing filter contamination.
- the size of natural plant based granules is greater than 2.0 mm, it is difficult to ensure uniformity of the quality of the cigarette filter because a uniform amount of granules may not be added to the cigarette filter.
- the moisture content of the natural plant based granules made under optimal granularization conditions is 5 to 12% of the total weight of the natural plant based granules, preferably 7 to 10%. If the granule has moisture content outside the above range, the granule may be broken, and the broken fine powder may cause filter contamination problems. Therefore, both productivity and quality of the cigarette filter to which the granule is applied may be deteriorated.
- the hardness of the natural plant based granules is preferably 90.0 to 99.0%.
- the weight ratio of the natural plant material and the binder is 98% : 2% and the hydroxy propyl methyl cellulose (HPMC) binder having the viscosity of 50 cps is used
- the hardness of the natural plant based granules may be in a range of 90.0 to 99.0%.
- the granule applied to the cigarette filter is not broken or deformed, and further, a target amount of the granule to be injected into the cigarette filter may be injected.
- the amount of the granule added to the cigarette filter is 3 mg/mm Tip, the maximum scent may be expressed, and the workability efficiency in applying the granule to the filter may be further improved.
- the present disclosure relates to a cigarette filter including a filter portion that accommodates the natural plant based granules therein.
- the natural plant based granules are not added to the cigarette filler portion, but are added to the cigarette filter portion.
- the natural plant scent is deformed via thermal decomposition or synthesis, thereby to induce bad odors (irritating odor, fish odor, burnt odor, spicy odor, sulfur odor, egg odor).
- the natural plant based granules are added only to the cigarette filter portion, and are not added to the cigarette filler portion, such that the original natural plant flavor is delivered to smokers while the natural plant scent is not deformed via thermal decomposition or synthesis.
- the cigarette filter according to the present disclosure is a cigarette filter further including a herb oil capsule containing an oil ingredient extracted from a natural plant material.
- a cigarette filter with increased natural plant fragrance and enhanced fragrance retention may be provided.
- the herb oil capsule may include an extract extracted from pine needle and rosemary based natural plant material.
- Pine needle extract includes pine, eucalyptus, rosemary, menthol, and MCTG as a pine needle natural oil, but is not limited thereto.
- cinnamon based rosemary may include orange, mandarin, cognac, ylang ylang, ling, genranium, menthol, benzyl bentoate, triethyl citrate, PG, and ethanol.
- the spicy based rosemary may include mandarin, ylang ylang, rosemary, lavindin, vitiver, cassia, Jasmine, menthol, benzoate, triethyl citrate, PG, and ethanol.
- the present disclosure is not limited thereto.
- the cigarette filter according to the present disclosure may be a single filter or the multiple filters.
- the cigarette filter according to the present disclosure may be a 27 mm single filter.
- the single filter may cause the problem in which granules are exposed and released to the outside.
- the cigarette filter according to the present disclosure may be a multiple filter.
- the multiple filter system may include a triple complex filter system having the cavity filter portion, a 15 + 12 mm double complex filter system, and a 9 + 18 mm double complex filter system, but is not limited thereto.
- the preferred cigarette filter system according to the present disclosure may be selected based on the added amount of the natural plant based granules and workability at which the granules are applied to the cigarette filler side portion (TE portion) and the mouth side portion (ME portion).
- the preferable examples of the cigarette filter system of the present disclosure may include a cigarette filter of a 9 + 18 mm double complex filter system and a cigarette filter of a 15 + 12 mm double complex filter system, but may not be limited thereto.
- a cigarette filter according to an embodiment of the present disclosure will be described in detail with reference to FIG. 1 to FIG. 4 .
- FIG. 1 to FIG. 4 are cross-sectional views schematically showing a cigarette according to embodiments of the present disclosure, respectively.
- the cigarette according to the present disclosure includes a cigarette filler portion 10 that is burned by fire and a cigarette filter portion 20 that filters cigarette smoke.
- the cigarette filler portion 10 and the cigarette filter portion 20 may be connected to each other by a tipping paper.
- the cigarette filter portion 20 may include a mouth side portion (ME portion) 22, the filler side portion (TE portion) 21, and optionally a cavity portion 23. Further, each of the portions 21, 22 and 23 may include fibrous or filamentary acetate tow.
- FIG. 1 is a schematic cross-sectional view of a cigarette including a cigarette filter of a 9 + 18 mm double complex filter system.
- the cigarette filter of the 9 + 18 mm double complex filter system of the present disclosure may include a filler side portion (TE portion) 21 made by adding natural plant based granules 31 to a fibrous or filamentary acetate tow, and a mouth side portion (ME portion) 22 composed of an acetate tow or a carbon fiber.
- TE portion filler side portion
- ME portion mouth side portion
- the natural plant based granules 31 may be added to the mouth side portion (ME portion) 22.
- the cigarette filter of the 9 + 18 mm double complex filter system of the present disclosure may include a mouth side portion (ME portion, 9 mm) 22 made by adding a herb extract (flavoring liquid) 32 to fibrous or filamentary acetate tow, and a filler side portion (TE portion, 18 mm) 21 made by adding natural plant based granules 31 or herb extract (flavoring liquid) 32 (10 ⁇ l) to the fibrous or filamentary acetate tow.
- the natural plant based granules 31 may be injected on an unfolded acetate tow band in a free falling manner, and then the acetate tow band may be rolled into a rod form.
- the herb extract may be different from the natural plant based granules and may be in a liquid or powder form.
- the herb extract may be a natural extract from a herb plant or a synthetic flavoring liquid.
- the herb extract of the present disclosure may be added using a spraying method or a nozzle based spraying method (TJNS).
- the spraying method may be an acid bath based spraying method.
- the herb oil capsules may be put into the filter using a capsule injection facility.
- the capsule injection facility may be a device disclosed in Korean Patent Application No. 10-2009-0101822 , but is not limited thereto. Various types of devices to inject the capsules into the filter may be used.
- the scheme of adding the herb extract or the herb oil capsule to the cigarette filter portion may be equally applied to a process of preparing another cigarette filter according to the present disclosure as described below.
- FIG. 2 is a schematic view showing a cigarette including a cigarette filter of a triple complex filter system including a cavity filter portion.
- a filler side portion (TE portion) 21 may be made of a fibrous or filamentary acetate tow or carbon fiber.
- a mouth side portion may contain natural plant based granules 31, and may further contain the herb extract (flavoring liquid) 32 in the fibrous or filamentary acetate tow.
- the natural plant based granules 31, each having a size of approximately 0.5 to 1.0 mm may be included in a certain area of the cigarette filter portion 20 in a filled form.
- the acetate tow may not be included therein.
- the filer filled with only the natural plant based granules 31 and free of the acetate tow may be referred to as a cavity filter.
- FIG. 2 includes a cavity portion 23 filled with the natural plant based granules 31.
- FIG. 3 is a cross-sectional view schematically showing a cigarette including a cigarette filter of a 15 + 12 mm double complex filter system (108 ⁇ 24.2 mm, PD 460 mm H 2 0).
- the cigarette filter of the 15 + 12 mm double complex filter system of the present disclosure may include a mouth side portion (ME portion, 15 mm) 22 having the herb extract (flavoring liquid) 32 added thereto, and a filler side portion (TE portion, 12 mm) 21 having the natural plant based granules 31 and the herb extract (flavoring liquid) 32 added thereto.
- the natural plant based granules 31 may be added to the mouth side portion (ME portion) 22.
- FIG. 4 is a schematic cross-sectional view of a cigarette including a cigarette filter of another 15 + 12 mm double complex filter system (108 ⁇ 24.2 mm, PD 460 mm H 2 0).
- a herb oil capsule 33 may be added to the filler side portion (TE portion, 12 mm) of the cigarette filter of the 15 + 12 mm double complex filter system according to the present disclosure.
- the cigarette filter of the 15 + l2 mm double complex filter system according to the present disclosure may include the filler side portion (TE portion, 12 mm) 21 having the herb oil capsule 33 added thereto, and a mouth side portion (ME portion, 15 mm) 22 having the herb extract (flavoring liquid) 32 having added thereto.
- the natural plant based granules 31 may be further added to the mouth side portion (ME portion, 15 mm) 22.
- the present disclosure provides a cigarette including the cigarette filter as described above.
- the cigarette according to the present disclosure may reduce methyl mercaptan as a halitosis inducing ingredient.
- the cigarette according to the present disclosure may reduce a cigarette odor inducing ingredient including ammonia, acrolein, crotonaldehyde, methyl ethyl ketone (MEK), 1,3-butadiene, acrylonitrile, benzene, and pyridine by 9 to 55%.
- a cigarette odor inducing ingredient including ammonia, acrolein, crotonaldehyde, methyl ethyl ketone (MEK), 1,3-butadiene, acrylonitrile, benzene, and pyridine by 9 to 55%.
- Example 24-2 has the highest reducing effect of the halitosis inducing ingredient, that is, methyl mercaptan. Example is not limited thereto. Other Examples and characteristics tests of the cigarettes according to the present disclosure may refer to in detail Examples 24-1 and 24-2 below.
- the cigarette filter according to the present disclosure may be prepared by a following preparation method.
- a preparation method of a cigarette filter including inserting a binder into a natural plant material to prepare natural plant based granules; drying and classifying the natural plant based granules; and adding the classified natural plant based granules to a cigarette filter, in which the binder is hydroxy propyl methyl cellulose (HPMC) of a viscosity of 50 cps, in which a weight ratio of the natural plant material and a binder is in a range of 95 to 99% : 5 to 1%.
- HPMC hydroxy propyl methyl cellulose
- the preparing of the natural plant based granules may include adding and dissolving 2% of hydroxy propyl methyl cellulose (HPMC) of a viscosity of 50 cps as a binder to 50% ethanol to produce a binder solution, and mixing pulverized natural plant powders and the produced binder solution with each other to form a mixture and stirring the mixture, and shaping and classifying the mixture.
- HPMC hydroxy propyl methyl cellulose
- the drying of the natural plant based granules may include one of freeze-drying, hot air drying, warm air drying, and fluidized bed drying.
- the natural plant based granules may be dried for 90 minutes to 300 minutes at a drying temperature of 40 degrees C to 70 degrees C, preferably, at a drying temperature of 45 degrees C for 90 minutes.
- the natural plant based granules with optimal granule physical properties and improved natural fragrance intensity may be obtained.
- a size of the classified natural plant based granule may be in a range of 0.25 to 2.0 mm and more preferably, 0.5 to 1.0 mm.
- a size of the classified natural plant based granule is smaller than 0.25 mm, the scattering (flying) amount of the granules increases during the cigarette filter preparation, thereby causing filter contamination.
- the granule size exceeds 2.0 mm, a uniform amount of the granules may not be injected into the cigarette filter, thereby to make it difficult to ensure uniformity of the cigarette filter quality.
- the natural plant based granules in the cigarette filter may be injected on an unfolded acetate tow band in a free falling manner. Then, the remaining granule is reused and added again thereto.
- the adding of the classified natural plant based granules to the cigarette filter may include further adding a herb extract (flavoring liquid) to acetate tow using an acid bath based spraying method or a nozzle based spraying method (TJNS).
- the method of preparing the cigarette filter may further include injecting a herb oil capsule containing an oil ingredient extracted from the natural plant material into the cigarette filter using a capsule injection facility.
- an added amount of the granules may be in a range of 0.5 to 4 mg/mm Tip.
- the added amount of the granules is smaller than 0.5 mg/mm Tip, the natural scent expression is low.
- the added amount thereof exceeds 4 mg/mm Tip, there may be a problem that the granules may not be added to the cigarette filter.
- LC/MS/MS analysis conditions were as follows: a column was Phenomenex Luna C18[2] 5 ⁇ m, 100A, 150 ⁇ 2.0 mm, a column temperature was 20 degrees C, and a sample injection amount was 10 ⁇ l.
- the filtering was performed using a 0.2 ⁇ m syringe filter, and then LC/MS/MS analysis was performed.
- the LC/MS/MS analysis experiment was based on a scheme in which the retention time of the sample may be significantly changed while slightly and continuously changing the concentration of the organic solvent in a mobile phase.
- the mass was analyzed based on a gradient method which is a useful method for a short separation time of a wide range of a hydrophobic molecular sample having a larger elution time.
- the organic solvent applied to the water-soluble filter (PVDF) in this experiment was 0.1% formic acid dissolved in water (H 2 O).
- the organic solvent applied to the oil-soluble filter (PTFE) was 0.1% formic acid dissolved in methanol (MeOH).
- kaempferol as the index ingredient of the pine needle was identified.
- recommended plants from which the index ingredient of the pine needle is obtained may be sea pine and Siberian pine but may not be limited thereto.
- the result of identifying the standardized quantification of the index ingredient of the pine needle via the LC/MS/MS analysis is shown in FIG. 5 (see FIG. 5 ).
- FIG. 5 shows the standardized quantification of the rosemary's index ingredient via LC/MS/MS analysis (see FIG. 5 ).
- the pine needle granules of Examples 1 to 11 were prepared by adding a binder to the raw material pine needle powers (leaf, stem, and root) and drying the mixture for 10 to 300 hours at 45 degrees C or 65 degrees C temperature condition.
- the weight ratio of the pine needle powder and the binder was 98% : 2%.
- the raw material pine needle (leaves, stems, and roots) was dried at room temperature to about 50 degrees C for 24 to 120 hours, and was pulverized using a grinder (pin crusher), and then classified with a 150 ⁇ m sieve. Powders passing through the 150 ⁇ m sieve were used.
- the binder employed a mixture of 2% hydroxy propyl methyl cellulose (HPMC) having one of viscosity 2, 15, and 50 cps, and 50% ethanol.
- the pine needle granule of Example 6 had the most desirable physical properties and natural fragrance expression effect, and thus was prepared.
- the crushed pine needle powders were put into a flow shear mixer (Germany, Lodige company).
- a binder solution containing a mixture of 2% of hydroxy propyl methyl cellulose (HPMC) of the viscosity of 50 cps and 50% alcohol was added thereto and the mixture was stirred.
- the mixture of the pine needle powder and the binder was shaped and was classified using a sieve of 0.25 to 2.0 mm in diameter, preferably 0.5 to 1.0 mm.
- the classified mixture was subjected to hot air drying at 45 degrees C for 90 minutes.
- the pine needle granules of Example 6 having a size of 0.5 to 1.0 mm was prepared.
- the pine needle granule prepared in Example 6 had physical properties of 98.1% hardness, 98.4% granularity, 0.431 g/cc filling density, and 7.9% moisture.
- the hardness of the pine needle granule prepared in Example 6 under optimal granularization conditions increased by 13.6% compared to that of the granule prepared in Example 1, and the total fragrance ingredient of the pine needle in Example 6 increased by about 60% compared to that of the granule in Example 11.
- Example 6 It was identified that the pine needle granule prepared in Example 6 as a preferred example had minimized moisture change in the cigarette filler and exhibited the greatest natural fragrance expression. However, the Example is not limited thereto.
- the physical properties and natural fragrance expression effect of the pine needle granules of Examples 1 to 5 and Examples 7 to 11 may also refer to Table 1 shown below.
- the rosemary granules of Examples 12 to 22 were prepared.
- the rosemary granule of Example 17 had the most desirable physical properties and natural fragrance expression effect, and thus was prepared.
- the rosemary granule prepared in Example 17 had physical properties of 92.0% hardness, 99.0% granularity, 0.436 g/cc filling density, and 9.9% moisture.
- the hardness of the rosemary granule prepared in Example 17 under optimal granularization conditions increased by 20% compared to that of the granule prepared in Example 12, and the total fragrance ingredient of the rosemary in Example 17 increased by about 100% compared to that of the granule in Example 14.
- Example 17 It was identified that the rosemary granule prepared in Example 17 as a preferred example had minimized moisture change in the cigarette filler and exhibited the greatest natural fragrance expression. However, the Example is not limited thereto.
- the physical properties and natural fragrance expression effect of the rosemary granules of Examples 12 to 16 and Examples 18 to 22 may also refer to Table 2 shown below.
- the natural plant materials applied to the cigarette filters of Examples 23-1 and 23-2 were herb oil capsules of two types based on rosemary and pine needle, herb extract (flavoring liquid) of two types based on rosemary and pine needle, and natural plant based granules of two types based on rosemary and pine needle.
- the natural plant based granules employed the pine needle granule of Example 6 and the rosemary granule of Example 17 which have the highest physical properties and natural scent expression effect of the granule, among the natural plant based granules prepared in Examples 1 to 22, and the cigarette filter containing them was prepared.
- Example 23-1 9 + 18 mm double complex filter preparation
- a cigarette filter of a double complex filter system was prepared which included a filler side portion (TE portion) 21 made by adding the natural plant based granules 31 to fibrous or filamentary acetate tow, and a mouth side portion (ME portion) 22 made of acetate tow or carbon fiber.
- TE portion filler side portion
- ME portion mouth side portion
- a cigarette filter having the natural plant based granules 31 added to the mouth side portion (ME portion) 22 was prepared.
- a cigarette filter of a double complex filter system composed of the mouth side portion (ME portion, 9 mm) 22 made by adding the herb extract (flavoring liquid) 32 to the fibrous or filamentary acetate tow, and a filler side portion (TE portion, 18 mm) 21 made by adding the natural plant based granules 31 and the herb extract (flavoring liquid) 32 (10 ⁇ l) to the fibrous or filamentary acetate tow was prepared (see FIG. 1 ).
- Example 23-2 Preparation of triple complex filter including cavity filter portion
- a cigarette filter of a triple complex filter system composed of the mouth side portion (ME portion) 22 made by adding the herb extract (flavoring liquid) 32 to the fibrous or filamentary acetate tow, a cavity portion 23 having the natural plant based granules 31 added thereto, and a filler side portion (TE portion) 21 made of the acetate tow or carbon fiber was prepared.
- a cigarette filter of a triple complex filter system in which the natural plant based granules 31 were added to the mouth side portion (ME portion) 22 was prepared (see FIG. 2 ).
- Example 23-3 15 + 12 mm double complex filter preparation
- the natural plant based granules employed a mixture at 2 : 8 ratio of the pine needle granule of Example 6 and the rosemary granule of Example 17 which have the highest physical properties and natural scent expression effect, among the natural plant based granules prepared in Examples 1 to 22, and the cigarette filter containing them was prepared as follows.
- a cigarette filter of a double complex filter system (108 ⁇ 24.2 mm, PD 460 mm H 2 O) composed of a mouth side portion (ME portion, 15 mm) 22 having the herb extract (flavoring liquid) 32 added thereto, and a filler side portion (TE portion, 12 mm) 21 having the natural plant based granules 31 and the herb extract (flavoring liquid) 32 added thereto.
- the cigarette filter in which the natural plant based granules 31 were added to the mouth side portion (ME portion) 22 was prepared (see FIG. 3 ).
- a cigarette filter of a double complex filter system (108 ⁇ 24.2 mm, PD 460 mm H 2 O) composed of a filler side portion (TE portion, 12 mm) having the herb oil capsule 33 added thereto, and a mouth side portion (ME portion, 15 mm) filled with fibrous or filamentary acetate tow was prepared.
- a cigarette filter in which the natural plant based granules 31 were further added to the mouth side portion (ME portion, 15 mm) was prepared.
- the herb extract (flavoring liquid) 32 may be added to fibrous or filamentary acetate tow using an acid bath based spraying method or a nozzle based spraying method (TJNS).
- Example 24-1 Preparation of cigarette including cigarette filter prepared in Example 23-1
- a cigarette was prepared by connecting a cigarette filter portion 20 prepared in Example 23-1 (9 + 18 mm double complex filter) and a secondary non-flavored filler portion 10 with each other (see FIG. 1 ).
- Example 24-1 The cigarette prepared in Example 24-1 was identified as having the following characteristics.
- Example 24-1 Using the cigarette prepared in Example 24-1, an experiment was conducted to analyze the carrying of the fragrance ingredient in the smoke based on the pine needle and rosemary.
- SPME fibers to be applied to 0.5 g of each sample of pine needle and rosemary were heated at 80 degrees C and were subjected to extraction for 30 mins. The process of pretreatment of the sample taking 5 minutes for fiber adsorption and 3 minutes for fiber removal proceeded.
- the fiber includes PA (polyacrylate), PDMS (polydimethylsiloxane), CAR (Carboxen)/PDMS, or PDMS/DVB (divinylbenzene), but is not limited thereto. PDMS/DVB (divinylbenzene) was used in this experiment.
- the fiber employed MPS (Multi Purpose Sampler) from GERSTEL and was injected to GC-MS (GC-MS in which 5973 MSD system and 5975C inert XL mass spectrometer from Agilent are connected to each other).
- MPS Multi Purpose Sampler
- GC-MS GC-MS in which 5973 MSD system and 5975C inert XL mass spectrometer from Agilent are connected to each other).
- the analysis of the fragrance ingredient carrying in the smoke based on pine needle and rosemary was conducted via quantitative analysis after pretreatment of samples of pine needle and rosemary.
- the smoking employed 20 cigarettes and a 44 mm filter pad.
- An impinger was connected thereto and the smoke was subjected to extraction alternately for 1 hour with 20 ml methanol (MeOH), and then was subjected to filtration through a 0.45 ⁇ m pore diameter PVDF filter.
- the pretreated sample was quantitatively analyzed via GC/MS, SIM mode analysis method.
- the fragrance carrying ingredient in the smoke of pine needle included borneol, bonyl acetate, 1,8-cineol, delta-cadinene, alpha-cadinene, limonene, and benzaldehyde. It was identified based on a result of the experiment that the fragrance carrying ingredient in the smoke of rosemary included borneol, bonyl acetate, 1,8-cineol, beta-caryophyllene, alpha-humulene, delta-terpineo1, and alpha-terpineol (see FIG. 6 ).
- DB-Wax column (length 30 m, I.D. 0.25 mm, film thickness 0.25 ⁇ m) from Agilent was used for efficient separation of fragrance ingredients from smokes of pine needle and rosemary in the quantitative analysis of fragrance ingredients in the smokes. Further, helium gas as inert gas was used as a carrier gas. A flow rate thereof was 1 ml/min, and the sample was injected into the instrument at an injection temperature of 250 degrees C in a splitless mode.
- a temperature program of GC-MS was set such that the temperature was maintained at 35 degrees C for 10 minutes, then was raised to 100 degrees C at a rate of 2 degrees C/min, and then was raised to 200 degrees C at a rate of 1 degree C/min, and then was raised at a rate of 3 degrees C/min to 230 degrees C, and then was maintained for 10 minutes.
- the separated ingredient enters MS along with the helium gas.
- the ion source was set to 250 degrees C
- the transfer line was set to 240 degrees C
- the quadrupole was set to 150 degrees C.
- the ionization energy was 70 eV, which was commonly used in electron impact (El).
- the cigarette was used to analyze the fragrance ingredients of pine needle and rosemary (see FIG. 7 ). Based on the experimental result, it was identified that some of the ingredients of the pine needle and of rosemary were carried in the smoke as shown in Table 5 below. Therefore, it was identified that the cigarette including the cigarette filter to which the natural plant material pine needle and rosemary based granules were applied had the possibility of expressing natural scent and imparting functionality.
- Example 24-1 Using the cigarette prepared in Example 24-1, an experiment was conducted to identify reducing ability for the methyl mercaptan as a representative halitosis ingredient in the cigarette smoke.
- Pine needle and rosemary based powders, granules, oils, and flavoring liquid, as well as pine needle based fragrance carrying ingredients, that is, alpha-pinene, bonyl acetate, and rosemary based fragrance carrying ingredients, that is, 1,8-cineol, and borneol were added to the cigarette filter.
- pine needle based fragrance carrying ingredients that is, alpha-pinene, bonyl acetate, and rosemary based fragrance carrying ingredients, that is, 1,8-cineol, and borneol were added to the cigarette filter.
- pine needle based fragrance carrying ingredients that is, alpha-pinene, bonyl acetate, and rosemary based fragrance carrying ingredients, that is, 1,8-cineol, and borneol
- a content of methyl mercaptan as used was 1 ppm [1 ⁇ g/ml] 2 ml.
- 10 mg of the sample was extracted with 2 ml of water and was used.
- 2 ml thereof was used.
- 3 ppm (3 ⁇ g/ml) of the sample was extracted with 2 ml of water and was used.
- the analysis experiment of reducing ability for methyl mercaptan included a pretreatment process of the sample, and the analysis process under the headspace sampler condition and the GC/MS-SIM condition.
- 10 mg of pine needle and rosemary based powders and granules sample were put into a 20 ml vial, which was immersed in 2 ml of water for 1 hour.
- 2 ml of 0.2 M potassium phosphate was added thereto and the pH was adjusted to 7.5.
- 2 ml of methyl mercaptan (1 ⁇ g/ml) was added thereto and the vial was sealed, followed by stirring with a Vortex mixer for 5 seconds.
- the GC/MS instrument based analysis conditions were set as follows. Headspace Sampler conditions were set as follows: culture temperature: 42 degrees C, culture duration: 6 minutes, and transfer liner temperature: 100 degrees C.
- the GC/MS-SIM conditions were set as follows: DB-624(60 m, 0.25 mm, 0.25 ⁇ m) column was used; Oven Temp: 35 degrees C for 10 minutes; post run: 250 degrees C for 30 minutes. Injector/Interface Temp was 150 degrees C or 220 degrees C.
- Split 10 1, flow rate 1 ml/min, methyl mercaptan ion (m/z): quantitative ion 47; and qualitative ion 48 and 45.
- Example 24-1 Using the cigarette prepared in Example 24-1, the sedimentation of halitosis ingredient thereof was measured via absorbance analysis. To this end, an experiment was conducted to identify the reducing ability for the halitosis ingredient derived from oral microbes when smoking the cigarette with the filter having the pine needle and rosemary based substances added thereto.
- the experiment for measuring the sedimentation of halitosis ingredients was as follows. Hydrogen sulfide in a volatile sulfur compound as mouth odor ingredient generated when cultivating oral bacteria in saliva was combined with iron in a liquid state such that iron sulfide (FeS) in a form of a black precipitate occurred. Thus, the sedimentation of halitosis ingredient was analyzed. First, whole saliva was incubated for 48 hours at 37 degrees C under anaerobic conditions. Then, 50 ml of oil based test substance or 20 ⁇ l of a single ingredient was added to 0.5 ml cultured saliva. 0.05 g surfactant was added thereto. The salvia was mixed with 0.05 g ferrous sulfate II (FeSO 4 ). The mixture was incubated for 24 hours at 37 degrees C under anaerobic conditions. Thus, absorbance of the culture was measured at 700 nm to determine sedimentation of halitosis ingredients.
- FeS iron sulfide
- Example 24-1 Using the cigarette prepared in Example 24-1, an experiment was conducted to identify reducing ability for stinking and toxic ingredients in cigarette smoke.
- Example 24-1 Using the cigarette prepared in Example 24-1, identification of smoke carrying ingredient among fragrance ingredients, identification of hazardous ingredient in smoke, sense or taste evaluation, function evaluation, safety evaluation, and storage evaluation were performed.
- Example 24-1 An experiment was conducted using the cigarette prepared in Example 24-1 to evaluate the taste or sense improvement of the cigarette and the effect of reducing the halitosis by the natural plant based granules.
- the pine needle granule-applied samples exhibited reduced odor and taste during smoking, and increase in smoothness of throat, increase in freshness in taste after smoking and decrease in unpleasant remaining odor.
- Example 24-2 Preparation of cigarette including cigarette filter prepared in Example 23-3
- a cigarette was prepared by connecting the cigarette filter portion 20 of the double complex filter system (108 ⁇ 24.2 mm, PD 460 mm H 2 O) prepared in Example 23-3 and the secondary non-flavored filler portion 10 to each other (see FIG. 4 ).
- Example 24-2 The physical properties of the cigarette prepared in Example 24-2 were identified.
- Example 24-2 The ingredients in the smoke of the cigarette prepared in Example 24-2 were identified.
- VSCs volatile sulfur compounds
- VSCs volatile sulfur compounds
- smoking causes the concentration of VSCs in the mouth to rise.
- the amount of volatile sulfur compounds carried into the smoke is around 1%, but a threshold thereof is very low and the odor thereof is irritating, that is, is rotten onion and garlic odor.
- Hydrogen sulfide (H 2 S) and methyl mercaptan (MM) were designated as analysis indicators to analyze halitosis inducing substances.
- the halitosis collection group included a total of 30 smokers who consumed Rejong Black cigarettes. Halitosis collection method was as follows: the smoker smoked one cigarette in each product and smoked for 2 minutes at 30 minutes intervals and the halitosis was collected (Tedlar Bag, 3L).
- the halitosis analyzer included a thermal adsorption and desorption system (TD-GC/MS) and PFPD (Pursed Frame Photometric Detector); TD/GC-PFPD conforming to an odor process test standard (notified by the National Institute of Environmental Sciences).
- H 2 S hydrogen sulfide
- methyl mercaptan as the halitosis inducing ingredient was identified to be reduced in a cigarette including the filter having the natural plant material (rosemary and pine needle) added thereto.
- the rosemary extract and rosemary oil capsule were applied thereto, methyl mercaptan decreased by 67.4%, and thus the reduction effect thereof was the highest.
- the pine needle extract and pine needle oil capsule were applied thereto, the methyl mercaptan was reduced by 30.7% (see Table 16).
- Example 242 Based on analysis result of the reduction percentage per tar of stinking and toxic ingredients carried into mainstream smoke of the cigarette prepared in Example 24-2, it was identified that in the cigarettes respectively including respective filters respectively containing rosemary extract and rosemary oil capsule (RE+RC), and pine needle extract and pine needle oil capsule (PE+PC) which reduced the methyl mercaptan as shown in FIG. 16, stinking and toxic ingredients were reduced by 12.4 to 29.2% (see Table 18).
- RE+RC rosemary extract and rosemary oil capsule
- PE+PC pine needle extract and pine needle oil capsule
- Example 24-2 safety evaluation of the cigarette including the filter containing natural plant materials, that is, pine needle and rosemary was conducted.
- Natural plant materials are added to non-burnable parts. Unlike a chemical substance composed of a single substance, a composition of the natural plant material is unclear. There is no use case in a cigarette thereof for the present purpose. Therefore, the evaluation was carried out in accordance with an in-house evaluation criteria for safety evaluation of additives to non-burned parts of tobacco.
- the contribution of the natural plant material to the cigarette smoke ingredient of the cigarette including the filter to which the natural plant material was applied was evaluated via a Purge & Trap analysis method. As a result, toxicity information thereof other than two rosemary ingredients and one pine needle ingredient registered as food additives of the USFDA was insufficient. The toxicity was at a high level (> 5 ppm). The ingredient was not present in the cigarette smoke. It was determined that the contribution thereof to biological activity was required.
- FIG. 10 shows the results of the Ames test of the mainstream smoke solid phase fraction (TPM) and the cell function effect evaluation of the mainstream smoke solid phase fraction (TPM) (see FIG. 10 ).
- Pine needle and rosemary natural plant materials are recognized as food raw materials (KFDA), and are limitedly applied to non-burnable areas of cigarettes. Individual ingredients thereof are present at a low concentration of 5 ppm or lower. The contribution thereof to the biological activity of the cigarette smoke is at a negligible level. Thus, when viewed comprehensively, it was determined that the pine needle and rosemary natural plant materials may be used in the filter at a current usage level.
- Example 24-1 Using the cigarette prepared in Example 24-1, the shelf-life or storage ability of the cigarette product having the filter containing the natural plant materials, that is, the pine needle and rosemary was verified.
- the experiment was conducted for the purpose of determining the life cycle according to the application of the natural plant material based granules to the cigarette products.
- Natural plant material based granules 3 mg/mm Tip were applied to the cigarette filter, and the experimental conditions were divided into dry season and rainy season conditions. In case of the dry season condition, the temperature was set to 15 degrees C and humidity was set to 45% RH. In case of the rainy season condition, the temperature was set to 25 degrees C, and humidity was set to 59% RH.
- the cigarette product of Example 24-1 was prepared. After one month has elapsed, problems in terms of the moisture content of the cigarette product and the change in the shape of the product, and the change of microorganisms therein were not identified. Thus, we verified good storage ability of the cigarette product including the filter to which the natural plant material based granule was applied.
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WO2009118816A1 (ja) | 2008-03-24 | 2009-10-01 | イビデン株式会社 | ハニカム構造体 |
KR101148157B1 (ko) | 2009-10-26 | 2012-05-23 | 주식회사 케이티앤지 | 향캡슐 담배 필터 제조 장치 및 그 제조 방법 |
US20110277781A1 (en) * | 2010-03-26 | 2011-11-17 | Philip Morris Usa Inc. | Methods for improving quality of mainstream smoke and multicomponent filters and smoking articles therefor |
US8327856B2 (en) * | 2010-03-30 | 2012-12-11 | Celanese Acetate Llc | Environmentally degradable cigarette filter |
CN103689796B (zh) * | 2013-12-03 | 2015-04-08 | 红云红河烟草(集团)有限责任公司 | 一种柠檬草多孔颗粒及其在卷烟中的应用 |
UA119657C2 (uk) | 2013-12-20 | 2019-07-25 | Філіп Морріс Продактс С.А. | Курильний виріб, який містить ароматичні гранули, що мають проникний зовнішній шар |
CN104705785B (zh) * | 2015-01-23 | 2019-01-01 | 南通醋酸纤维有限公司 | 一种醋酸纤维素微粒聚集体及其制备方法与应用 |
CN105167190B (zh) * | 2015-06-17 | 2018-10-09 | 湖北中烟工业有限责任公司 | 烟用黄酮香精烟珠及其制备方法 |
CN106617285B (zh) * | 2016-09-27 | 2019-11-08 | 湖北中烟工业有限责任公司 | 一种变色烟用香料珠及其制备方法 |
CN106666825B (zh) * | 2017-02-04 | 2019-10-29 | 云南热丽康生物科技有限公司 | 一种添加紫杉植物颗粒的卷烟滤棒制备方法 |
CN110013806B (zh) * | 2019-04-17 | 2021-10-26 | 云南中烟工业有限责任公司 | 一种石墨烯-植物多孔复合微球及其制备方法与应用 |
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2019
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2020
- 2020-09-23 CN CN202080005368.0A patent/CN113068396A/zh active Pending
- 2020-09-23 WO PCT/KR2020/012807 patent/WO2021080193A1/ko unknown
- 2020-09-23 US US17/275,127 patent/US20230071441A1/en active Pending
- 2020-09-23 EP EP20851271.5A patent/EP3834635B1/en active Active
- 2020-09-23 JP JP2021505705A patent/JP7164097B2/ja active Active
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US20230071441A1 (en) | 2023-03-09 |
JP7164097B2 (ja) | 2022-11-01 |
JP2022510070A (ja) | 2022-01-26 |
WO2021080193A1 (ko) | 2021-04-29 |
EP3834635A1 (en) | 2021-06-16 |
CN113068396A (zh) | 2021-07-02 |
EP3834635A4 (en) | 2021-12-29 |
KR20210049537A (ko) | 2021-05-06 |
KR102288257B1 (ko) | 2021-08-10 |
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