TW568754B - Aromatized smokable articles - Google Patents

Abstract

Aromatized smokable articles are described which contain, in their wrapper made from in particular paper or tobacco, special glycosides which can be applied in many different and improved ways and, upon smoking of the article, release an aroma component, which aromatizes the side-stream smoke.

Description

568754 V. Description of the Invention (Printed by A7, Consumer Cooperative of Employees of Intellectual Property Bureau, Ministry of Economic Affairs) The present invention relates to smoke-extracting objects which contain special aromatic substances in the aromatized tributary cigarettes of the outer leaf curl, and the present invention relates to a smoke-extracting cigarette When using smoke-extracting objects such as cigarettes, cigars and cigars, the so-called tributary smoke is caused by the continuous burning of tobacco leaves during the pause period of smoking. Tributary smoke is often particularly uncomfortable and disturbing for non-smokers. In order to cope with this problem, many possible solutions have been proposed. Taking conventional cigarettes as an example, the solution includes reducing the amount of tributary smoke or improving the odor by aromatizing tributary smoke. The aromatic substances described in the method described below are preferably applied. To the outer leaves of tobacco products. This kind of application is better than the aromatization treatment of tobacco leaves, because it allows the aromatic substances to be transferred into the tributary tobacco more effectively without affecting the taste of the tobacco. As the volatility of most of the effective aromatic substances has been proven These substances are preferably used in a chemical or physical combination to avoid aroma during storage. Lost and unlit odors of smokeable objects that can be smoked. The combination method is better to be able to be split by thermal decomposition, so the heating process triggers the release of aromatic components during smoking. Thus, US-A-4,804,002 suggests the use of aromatic components. The glycoside treatment can suck out the leaf curl outside the tobacco object, but actually only investigates the glucoside. When the object is burned, the aromatic components are released by the glucoside, which has a positive effect on the odor of tributary smoke, and the mainstream smoke Taste has not been significantly changed. Among the suggested glucosides, mainly ethyl vanillylglucoside (ethylvanillin glucoside) has the desired effect. In this regard, the glucosides of maltitol and menthol only show weak (Please read the notes on the back before filling this page)

• I ^ ^ -------- tr --------- (Please read the precautions on the back before filling out this page) Printed by the Employees' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 568754 A7-—- --- ^ B7 V. Description of the invention (2) A method for producing the outer roll leaves of glucosides that can be sucked out of tobacco products on a large scale does not come from US_A_4,804,002. Instead, only a small amount of test cigarettes were made by applying a glucose-worn ethanol-based solution to the outer leaves using a microliter syringe. In addition, a cigarette is known from US-A-4,941,486, in which the outer rolled leaf is in close contact with the aromatic substance. In particular, ethyl vanillin glucose is used to bind aromatic substances. Impregnation, application of films, use of adhesives for press-fit mixing, electricity / waste, printing, and cigarette adhesive seam adhesives are all possible methods of introducing aromatic shellfish into the outer leaves. However, no details have been provided about the actual procedure, such as the type and concentration of solution used or its technical practices. The example uses only the adhesive press technology. In addition to the methods listed in US 4,941,486 for impregnating tobacco leaf materials with glycosides, the following two methods are used: 1 · Leaf materials other than smokeable articles such as cigarette paper or sheet tobacco It is usually manufactured according to current general papermaking methods. This method often uses a long spray cup for spraying the draconisyl glycoside solution to provide a single-sided spray on paper or on the leaf membrane. Such unilateral application of glycocalyx to the inside or outside of the outer rolled leaf additionally allows for more selective control of pyrolysis. 2. Another type of impregnation is the application of a furanyl glycoside solution in a trace amount directly to a rolled leaf by a cigarette making machine. Such a required device can be supplied, for example, by KAYMICH Company, Sheffield, UK under the name of FAS or MAS, so this method is also called the Carmich method. The applicator uses a row of nozzles to provide a solution using a metering pump. The latter two methods do have the disadvantage that the amount of solvent that can be applied is extremely small. This paper size applies the Zhongguanjia Standard (CNS) A4 specification ⑵G x 297 public love) 568754 A7 B7 V. The invention description printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs (in the method, the further processing of the diaphragm due to the large amount of solvent Causes a high degree of wetting and big 5: Harm. Take the Kelvin method as an example, excessive wet paper contact with tobacco will cause undesired marks on the cigarette. It is known that the Kelvin method can only be applied up to the weight of the cigarette paper 20% aqueous solution. For larger quantities, contamination appears on the finished cigarette. However, in order to achieve the full aromatization of tributary cigarettes using the known glucose solution, that is, the succulents of the cool class, it is usually necessary to use The outer roll leaves weigh up to 1% of glycosides. In order to prevent the aforementioned problems caused by the use of large amounts of solvents, it is necessary to use a solution containing at least 5% by weight of glucose. It is known that the solubility of aromatic substances in water is extremely low and cannot be used for this purpose. . So the solubility of ethyl vanillin malt in 2 (rc is only about 2% by weight. Since this concentration is far from enough, it must be used warm Relatively tested. When using Camesh method to immerse the outer roll leaves, ethyl vanillin maltoside crystallized at the tip of the nozzle, resulting in blockage of the nozzle and interruption of the test. The need to use a warm solution has significant further disadvantages. For example, the appearance of the device is significantly increased, and the storage of the solution is reduced. Therefore, the object of the present invention is to provide a smokeable object, which has an aromatic substance on the outer leaf of the leaf, and aromatizes tributary cigarettes. It is easy to borrow different methods. Manufactured in large quantities and using an aqueous solution with a higher degree of aromatic substances, especially by applying the aromatic substances using a nozzle. The unexpectedness of this project can be achieved by aromatizing smokeable articles according to the present invention. According to the present invention The smokeable tobacco article has an outer roll leaf, which contains at least one aromatic substance that can aromatize tributary cigarettes, and is characterized in that the / aromatic substance is a disaccharide, an oligosaccharide, or a glycoside of a polysaccharide and an aromatic component. This paper scale applies to China National Standard (CNS) A4 Specification (210 X 297 Public Director 568754 A7

Precautions

Please read first. Read on the back 568754 Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

A7 B7 V. Description of the invention (5) The thermogravimetric analysis of ethyl vanillin maltoside which is preferably used for smoking objects according to the present invention, and the sensory properties of the tributary cigarettes of such cigarettes after soaking are described in the examples. . The examples show that the decomposition temperature and sensory evaluation of tributary smoke correspond to the values determined for conventional ethylvanillin maltoside. Therefore, the advantage of the smokeable article according to the present invention is that it can be used for the same aromatized tributary cigarettes. Since the solution performance of disaccharides, oligosaccharides, or polysaccharide glycosides is improved, the range of application methods can be significantly expanded. In particular, the advantageous method of directly applying a glycoside using a nozzle on a cigarette making machine by using the Camille method to manufacture a smokeable article can be selected. The rolled leaves of the article according to the invention include in particular paper or tobacco leaves. Particularly good is composed of paper or flakes on leaves. You can also use multiple leaves, or you can use a combination of paper and tobacco leaves. Natural outer leaves can also be used as the outer layer. It is particularly preferred to use an outer leaf material such as paper containing a substance that reduces the particulate matter of tributary smoke. Cigarette paper provided with special fillers such as hydroxide hydroxide, magnesium oxide or mixtures thereof is preferably used for this purpose. Cigarette paper is usually used in the form of a single layer or a double layer when it is used as the outer rolled leaf. In the case of a single layer, for example, glycosides can be directly applied to paper excellently, and in the case of a double layer, it is applied to an outer layer. In the later-mentioned version, it is preferred to use a paper with reduced tributary smoke as the inner layer and a conventional cigarette paper as the outer layer. The outer leaf of the object according to the present invention is particularly composed of one or two layers of leaves. If a double-layered sheet is used for the leaf ', the outer layer preferably contains sugar 4. So cigarettes and light snow & leaves are usually provided with glycosides. In addition to using the aforementioned impregnation method for paper, made from sheet-shaped terminal leaves (please read the precautions on the back before filling this page) Order ---------

Applicable to this paper standard: Home Standard (CNS) A4 specification ⑵g χNuogong loved 568754 printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs, printed A7 V. Description of the invention (60% of the outer leaf can also be based on the so-called slurry method Manufactured. After grinding, the binder solution is mixed with the grass powder, spread on the heated strip and then dried. In this case, the glycoside can be applied to the binder solution to form a sheet-shaped tobacco leaf impregnated with the glycoside. In general, the smokeable article according to the present invention can be manufactured by providing rolled leaves with glycosides, especially in the form of a film. The glycosides are preferably used in the form of an aqueous solution with a glycoside content of 5% by weight or more. The preferred sugar syrup is to apply (a) the sugar syrup solution to the outside or inside of the outer leaves, (b) use viscose compression, or (0 directly apply the glycoside solution using a nozzle. If sheet tobacco is used As the outer rolled leaf, it can be manufactured according to the papermaking method or the slurry method. In the first case, the application is performed according to the process described in 0) to ((:). In the second case, the glycoside can be added to the cohesion The solution used for the object according to the present invention is provided with a natural outer leaf of Xuesu or Xiaoxue%, for example, the application can be performed by spraying the outer leaf with a glycoside aqueous solution, otherwise the glycoside is dissolved in the viscose and glued to the sticky leaf And the outer leaves. In this case, the increase in water solubility of the glycosides used according to the present invention proves to be excellent. Finally, it is particularly excellent. The glycosides of disaccharides, oligosaccharides, or polysaccharides used in accordance with the present invention can be combined with furanyl Glycosides and special furanosyl glucosides. Furanosyl glycosides release furanosyl alcohol when smoking smoke. Because of its aroma, it can cover non-tobacco aromas such as ethyl vanillin without causing it. Positive effects, such as smoke is less irritating or less fresh. 'Paper size applies Chinese National Standard (CNS) A4 (210 X 297 mm) ^ -------- tr ------ --- ^ Awi. (Please read the precautions on the back before filling out this page) 568754 A7 B7 V. Description of the invention (in the following we will use examples to explain the progress of the invention-details. Examples

Preparation of Ml. Ethyl vanillin maltoside 亳 g (2. 0 mol) ethyl vanillin in 4.4 ml 0.45 mol concentration X hydroxide _ solution in methanol solution was slowly added dropwise to 1 ^ g (2.2 mol) A solution of acetamidine maltose in 9 liters of absolute digas methane. The mixture was stirred at room temperature for 3 hours and then poured into a 20 liter ice-water mixture. 'The combined organic phases were dehydrated over magnesium sulfate. The solvent was removed, and the residue was purified by silica gel using column chromatography (eluent: petroleum / ethyl acetate g 1: 1: 1). Order yield: 341 mg (0.43 mmol, 22%) of ethyl vanillin maltoside protected with ethyl. For deacetylation reaction, 982 mg (1.25 mmol) of protected maltoside was suspended in 15 ml of absolute methanol and mixed with 15 ml of a 1% sodium methoxide solution. After stirring for 10 minutes, the maltoside was completely dissolved and neutralized with Amberlite IR-120 (ΓΓ). The ion exchanger was removed by filtration and the solvent was removed in vacuo. Purification was performed by recrystallization from 95% ethanol. 520 mg (1.06 mmol, 85%) of ethylvanillin maltoside was obtained as a white solid. (4-Methylmethyl-2-ethoxyphenyl) -4-0-a glucose π glucopyranosyl, glucosinolide (ethylvanillin maltoside) ... ^ 33 (^ 3 (490.46 g / Mol)] 2〇 / 578 vomit 2 degrees (c (M, H20)

Melting point: 199 ° C The paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) 568754 A7 ---- B7___ 1. Description of the invention (8) Elemental analysis (please read the precautions on the back before filling This page) Calculated: C 51.43 Η 6.17 Measured: C 50.97 Η 6.22 Mass Spectrum: MALDI-TOF-MS: m / z = 513.2 [M + Na], 529.2 [Μ + Κ] iH-NMR (400 MHz , D, 0) δ = 9.67 (s, 1H, CHO), 7.49 (dd, 1H, aryl H-5), 7.43 (d, 1H, aryl H-3), 7.21 (d, 1H, aryl 6), 5.38 (d, 1H, H-1 '), 5.19 (d, 1 h, hl), 4.08-4.17 (m, 2 H, 0-CH2-CH3), 3.62-3.89 (m, 10 H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-3 ', H-5 ,, H-6 ,, H-6, b), 3.53 (dd, 1H, H-2,), 3.37 (dd-t, 1H, H-4 '), 1.36 (t, 3H, 0-CH2-CH3) ppm.

Ji ， 2 = 7.6; Jr 2, = 4 · 1; J2, 3, = 9.7, J3, 4, = 9 · 7, j4, 5, = 9.7, Jar-3, ar-5—1.5, Jar_5ar_6 = 8.1 , 〇Et = 7.1 Hz 〇13C-NMR (] 00.6 MHz ^ P2P) 5 = 195.11 (CHO) ^ 151.62, 148.36 (2 x C, aryl Cl, aryl C-2), 131.31 (aryl (3 -4), 126.94 (aryl C-5), 115.34 (aryl C-6), 112.99 (aryl C-3), 100.07 (Cl,), 99.78 (Cl), 76.74 (C-5), 76.21 (C-3), 75.24 (C-4), 73.23 (C-2), 73_ll (C-5,), 72.86 (03,), 72.06 (C-2 '), 69.69 (C-4,), 65.68 (0-CH2-CH3), 60.85, 60.80 (2 x C, C-6, C-6 '), 15.37 (0-CH2-CH3) ppm. Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs: Hot weight The analysis below shows a decomposition curve obtained by thermogravimetric measurement (heating rate: minutes) of ethylvanillin maltoside used in the smokeable article according to the present invention.

568754 A7 V. Description of the invention (1G) water condensate and 0.6 g smoke nicotine). As the tobacco blend, a commercially available American compound blend is used. The commonly used cigarette paper (porosity 40 CU) was used as the outer rolled leaf of the cut tobacco. Ethylvanillin maltoside was applied to the paper using an applicator from the Camelot method (Shelfield, UK), while cut tobacco was produced on a cigarette making machine. Different doses were tested, each cigarette containing 0.15 and 0.6 mg glycosides. For this test, a solution of glycosides in warm water (temperature 50. []) was fed at a concentration of 75 g / l to a storage container of glycosides. The container was equipped with a heater to maintain the solution temperature at 40 ° C. The application to the paper is performed by drawing the paper through a metal block provided with a boring hole, that is, a nozzle, before the cut tobacco is formed. The dose was controlled by pump pressure setting, so relative to the weight of cigarette paper (40 mg / cigarette), a 5% weight ratio glycoside solution was applied to the outer roll leaves as a lower dose and 28% weight ratio as a higher dose. The sensory evaluation of tributary smoke from samples printed by the Intellectual Property Office was performed by a group of trained smokers and non-smokers, and compared with similar cigarettes but without aromatic glycosides in the cigarettes. The sample mechanically draws smoke in a room of a known size and with specific equipment (for example, a room with a volume of 20 cubic meters has 5 cigarettes). The fresh smoke was evaluated immediately, and the old smoke was evaluated 6 hours later. The reviewer stated on the Zhang questionnaire how strong the aroma (here, ethyl vanillin) is, and how significant non-pleasant properties, such as dazzling, are associated with cigarettes. The evaluation was performed at a dose of 0.15 mg glycoside / cigarette in accordance with the statistical standard known in sensory tests. The irritant effect of smoke was significantly reduced without identifying the aroma of ethylvanillin itself. At a higher dose of 0.6 mg, this paper is sized for China National Standard (CNS) A4 (210 X 297 public love) 568754 A7

Glycoside / cigarette ’s aroma released during smoking is more obvious (printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs)

The sweet smell, that is, the smell of vanilla, further reduces the irritating effect of smoke. If the evaluation is not carried out immediately, but after 6 hours have elapsed, the smoke in the laboratory is described as stale after the cigarettes are smoked by the cigarettes for comparison of glycosides used in accordance with the present invention. Taste "and musty. The old smoke of cigarettes with ethylvanillin maltoside is obviously less pleasant. Example 4 · Manufacture of g cigarettes with ethyl vanillin maltoside and sensory evaluation of tributary cigarettes for comparison purposes. The cigarettes according to Example 3 were manufactured and evaluated, but contained aromatic substances on the outer leaves of tobacco shreds. f is the conventional ethylvanillin maltose for different doses of 0 μm / cigarette. Because of its poor solubility in water ', a higher dilution is required. This application of sugar is performed by a separate step of spreading on paper and then paper. The evaluation of the resulting cigarettes was performed in the same way by a trained reviewer describing the effect on tributary smoke is the same as that of ethylvanillin maltoside. * Application: Provides universal furanyl glucoside with ethylvanillin maltose Manufacture of mixture cigarettes and sensory evaluation of tributary cigarettes Bite nicotinyl glucoside ((2,5-dimethylmethoxy_digas bitan * yl-D-glucopyranose) is first based on R · r 〇Scher et al. Phytochemicals 43 (1), 155 (1996) Manufactured by the procedure of the reference document. Manufacture of cross-flavored incense paper with a diameter of 7.9 mm and a total length of 84 mm (extra large size). National Standard (CNS) A4. Specifications (210 X 297 public love) ί-I -------- tr --------- (Please read the notes on the back before filling out this page) 14 568754 A7 V. Description of the invention ( Employees of the Intellectual Property Bureau of the Ministry of Economic Affairs print cigarettes and then manufacture them (21 mm monoacetate filter, 63 mm length of tobacco shreds, tobacco weight 750 mg, mixture type: American compound, filter ventilation rate 20%, smoke Information based on ISO specifications at an aspirate value of 8 (^ 118 mg anhydrous condensate and 0.8 6 mg of nicotine). Cigarette paper for general commercial use is used as a shredded tobacco leaf and is provided with a mixture of 0.5 mg ethyl vanillin maltoside and 0-3 mg raninyl glucoside per cigarette. Evaluation of cigarettes It was carried out as described in Example 3. Compared with general commercial cigarettes, tributary smoke obviously felt more pleasant, with less irritation (fresh smoke) and less staleness (old smoke). No non-tobacco odor or taste was determined. Example 6: Production of cigarettes with a mixture of ethylvanillin maltoside and furanyl glucoside and sensory evaluation of tributary smoke. Filter cigarillos with a diameter of 7.9 mm and a total length of 84 mm were manufactured. It consists of leaf tobacco made by the method, which is impregnated with the furanyl glucoside and ethyl vanillin maltose mixture described in Example 5. The application of this aromatic mixture is performed in a rubber press during the manufacturing process of the outer leaves. The evaluation of the obtained Xiaoxuesu Yu was performed as described in Example 3. By using the aromatic mixture to roll out the leaves on the outside, the odor score "Snow% boat air is less than alkaline odor" feels greatly reduced These small cigar smell - like a more obvious than cigarettes grapes its collapse glycosides sticky plant.

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Claims (1)

568754 on (λ / 5 " VI. Patent Application No. 891248G7 Special Patent Application Request for Amendment of Patent Scope "Year Called ^ Day 1.-A smokeable object 'has an outer leaf which contains at least one Aromatic recording and aromatizing tributary cigarettes, where the aromatic substance is a kind of double-squash sugar or polysaccharide and a sugar component of an aromatic component. 2. For the object of the scope of patent application 1, it is characterized by the double-brew, oligosaccharide The sugar or polysaccharide is maltose 'lactose or cellobiose. 3. The item according to the scope of patent application! Or item 2, wherein the aromatic component is vanillin, ethylvanillin, citron, menthol, menthol or maltitol. 4. If the item in the scope of the patent application is applied to the item 'wherein the seeding leaf contains paper or leaves. 5. If the object in the scope of the patent application is the substance of the particulate matter flowing from the smoke. 6. If the scope of the patent application is in the first category The total amount of items relative to the weight of the outer rolled leaf is 0-1 to 5% by weight. 7. The article of the first scope of the patent application, wherein the outer rolled leaf is composed of a layer of paper. Item 1 Paper composition and outer layer contains sugar 9 · If the object of the scope of the patent application item 8 is a filler of particulate matter. 10 · If the object of the scope of patent application item 9 is magnesium oxide or a mixture thereof as a filler. 11 · As the object of the scope of patent application item 1 (Please read the note on the back first? Then write this page} where δ HAI paper contains glycosides that can reduce the presence of the outer roll leaves — where the outer roll leaves are composed of two layers in which the inner layer contains reduce branches There is a hydroxide town, where the outer rolled leaf system consists of a layer of the original _ scale suitable for wealth _ house standard half ㈣) specifications (2 297 to 16-568754) VI. Patent application scope ABCD # Sheet shape on the leaf. 12 · For example, the article in the scope of patent application, wherein the outer leaf is composed of two layers of leaves on the leaf, and the outer layer contains furfurin. 13. The article in the scope of patent application, wherein the outer leaf is composed of one layer The inner layer of sheet tobacco and the outer layer of paper and the outer layer contain glycocalyx. 14. A method of manufacturing a smokeable tobacco article as claimed in any one of the claims 1 to 13, wherein the outer leaf is provided with a glycoside. 15 · such as The method according to item 14 of the patent, wherein the glycoside is used in the form of an aqueous solution, and the glycoside content is greater than or equal to 50 /. By weight ratio. 16. The method according to item 14 or 15 of the application, wherein the glycoside is borrowed The following methods are applied to the outer leaf (a) spraying the glycoside solution to the outside or inside of the outer leaf, (b) using viscose lamination, or (c) directly applying the glycoside solution using a nozzle. The method according to item 14 or 15, wherein the outer rolled leaf is made into a film form by mixing the ground tobacco powder and an aqueous solution of a glycoside-containing binder. 18 · —Aromatically sucking out the rolled leaf outside the tobacco object, the The outer roll leaves contain a disaccharide, sugar collection or polysaccharide and an aromatic glycoside as an aromatic substance. The paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) gutter 17.