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EP1231849A2 - Article aromatise a fumer - Google Patents

Article aromatise a fumer

Info

Publication number
EP1231849A2
EP1231849A2 EP00987279A EP00987279A EP1231849A2 EP 1231849 A2 EP1231849 A2 EP 1231849A2 EP 00987279 A EP00987279 A EP 00987279A EP 00987279 A EP00987279 A EP 00987279A EP 1231849 A2 EP1231849 A2 EP 1231849A2
Authority
EP
European Patent Office
Prior art keywords
glycoside
article according
paper
tobacco
smoke
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.)
Granted
Application number
EP00987279A
Other languages
German (de)
English (en)
Other versions
EP1231849B1 (fr
Inventor
Thomas Pienemann
Gunther Peters
Hans Noe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Reemtsma Cigarettenfabriken GmbH
Original Assignee
Reemtsma Cigarettenfabriken GmbH
HF and PhF Reemtsma GmbH and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Reemtsma Cigarettenfabriken GmbH, HF and PhF Reemtsma GmbH and Co filed Critical Reemtsma Cigarettenfabriken GmbH
Publication of EP1231849A2 publication Critical patent/EP1231849A2/fr
Application granted granted Critical
Publication of EP1231849B1 publication Critical patent/EP1231849B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A24B15/282—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by indirect addition of the chemical substances, e.g. in the wrapper, in the case
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
    • 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
    • A24D1/02—Cigars; Cigarettes with special covers

Definitions

  • the present invention relates to smokable articles which contain special aroma substances in their wrapping in order to aromatize the by-pass smoke, as well as a wrapping for smokable articles.
  • US Pat. No. 4,804,002 proposes treating the wrapper of a smokable article with glycosides of an aroma component, only glucosides being specifically examined.
  • the aroma component is released from the glucoside and can thereby have a positive effect on the smell of the bypass smoke without the taste of the mainstream smoke being changed appreciably.
  • the ethylvanillyl- ⁇ -D-glucopyranoside ethylvanillin glucoside
  • a method which can also be used on a production scale for applying the glucosides to the casing of a smokable product is, however, not apparent from US Pat. No. 4,804,002. Rather, only small quantities of test cigarettes are produced by applying an ethanolic solution of the glucosides to the casing with the aid of a microliter syringe.
  • a cigarette is also known from US Pat. No. 4,941,486, the wrapper of which is in close contact with a bound flavoring agent.
  • Ethylvanillin glucoside is used primarily as a bound flavoring agent.
  • Impregnation, application of a film, introduction via a size press, electrostatic deposition, printing and incorporation into the seam glue of the cigarette are mentioned as possible methods for applying flavor to the wrapper.
  • there is no information about made the concrete procedure when loading e.g. type and concentration of the solutions used or their technical implementation. Only the size press technology is used in the exemplary embodiments.
  • Wrapping materials for smokable articles are usually manufactured using common paper-making processes. Such methods often provide for one-sided spraying of the paper or tobacco fleece with the aid of a spray bar, which could be used to apply a solution of the glycoside.
  • the possible one-sided application of the glycoside either on the inside or outside of the casing could also enable more targeted control of the pyrolytic decomposition.
  • a very flexible way of impregnation could also be to apply a solution of the glycoside in the form of traces to the wrapping directly on the cigarette machine.
  • a device required for this is e.g. offered by the company KAYMICH, Sheffield, UK, under the designation FAS or MAS, which is why this process is referred to below as the KAYMICH process.
  • the device works with a series of nozzles, which are supplied with the solution by a dosing pump.
  • glucosides i.e. Glycosides of a simple sugar
  • amounts of 1% glucoside, based on the weight of the coating are required.
  • a total of solutions with a content of at least 5% by weight of glucoside must be used.
  • the water solubility of the known flavorings is too low for this.
  • the solubility of ethylvanillin glucoside at 20 ° C is only about 2% by weight. Since this is far from sufficient, a warm solution would have to be used.
  • the ethyl vanillin glucoside crystallized at the nozzle tips, which led to blockage of the nozzles and thus to the test being stopped.
  • the need to use warm solutions also has considerable further disadvantages, such as significantly increased equipment expenditure and reduced storage life of the solutions.
  • the invention is therefore based on the object to provide smokable articles with flavorings in their wrapping for aromatizing the sidestream smoke, which can be obtained in a simple manner by means of various processes in large quantities and using aqueous solutions with an increased concentration of flavoring material, and in particular also by application of the aroma substance can be produced by means of nozzles.
  • This object is surprisingly achieved by the flavored and smokable articles according to the invention.
  • the smokable articles according to the invention have a casing which contains at least one aroma substance for aromatizing the side-stream smoke, and are characterized in that the aroma substance is a glycoside of a two- or multiple sugar and an aroma component.
  • the invention also relates to the wrapper for smokable articles, which is characterized by a glycoside content of a double or multiple sugar and an aroma component as an aroma substance.
  • Maltose, lactose or cellobiose is preferably used as the double or multiple sugar and thus the sugar component of the glycoside.
  • All flavoring compounds which can be linked to the double or multiple sugar via a glycosidic linkage can be used as the flavor component of the glycoside.
  • Preferred aroma components are vanillin, ethylvanillin, eugenol, menthol or maltol.
  • the amount of all glycosides present in the casing is 0.1 to 5% by weight, based on the weight of the casing.
  • the special glycosides present in the smokable articles according to the invention allow, due to their special sugar component, simple application by means of different processes and thus mass production of the articles according to the invention. They can be used in the form of highly concentrated aqueous solutions for impregnating the wrapper of the smokable article. It is particularly advantageous that, when applied by means of nozzles, in contrast to the known glycosides, the nozzles are not clogged.
  • glycoside used according to the invention such as ethylvanillin maltoside
  • the tendency to crystallize is significantly reduced in comparison to ethylvanillin glucoside, which means that even more concentrated solutions can be used and the impregnation of the coating is thus made even easier.
  • the smokable articles according to the invention preferably contain tobacco as the smokable material. They are therefore particularly in the form of cigars, cigarillos and cigarettes.
  • the smokable articles according to the invention therefore offer the advantage, with the same aromatization of the sidestream smoke, that because of the improved solution behavior of the glycosides of two or multiple sugars used, the spectrum of the exposure methods available could be expanded significantly.
  • the wrapping of the articles according to the invention has in particular paper or tobacco. It is particularly advantageously made of paper or film tobacco.
  • the wrapping can also be multi-layered, whereby combinations of paper and tobacco can also be used.
  • a natural cover sheet can also be used as the outer layer.
  • wrapping materials such as e.g. of papers that contain substances to reduce the particle mass of the sidestream smoke.
  • special fillers e.g. cigarette papers provided with magnesium oxide, magnesium hydroxide or a mixture thereof.
  • cigarette paper when using cigarette paper as wrapping, it is used in one or two layers.
  • the glycoside is advantageously applied directly to the paper in the case of a single-layer form and to the outer layer in the case of a two-layer form. In the latter embodiment, it is preferred to use the sidestream-reducing paper for the inner layer and conventional cigarette paper for the outer layer.
  • the wrapping of the article according to the invention can in particular also consist of one or two layers of film tobacco. If two-layer film tobacco is used, it is preferred that the outer layer contain the glycoside. Accordingly, in the case of cigars and cigarillos, the cover sheet is usually provided with the glycoside.
  • wrappings made of film tobacco can also be produced using the so-called slurry process.
  • ground tobacco dust is mixed with an aqueous solution of binders, scraped onto a heated belt and then dried.
  • the glycoside can be added to the aqueous binder solution, which results in impregnated film tobacco.
  • the smokable articles according to the invention can be produced by providing the coating, in particular in sheet form, with the glycoside.
  • the glycoside is preferably used in the form of an aqueous solution which contains the glycoside in an amount of greater than or equal to 5% by weight.
  • glycoside is preferred by the glycoside.
  • film tobacco is used as the wrapper, it can be produced either by the paper or by the slurry process.
  • the application takes place according to the procedures already mentioned above under (a) to (c).
  • the glycoside can be added to the aqueous binder solution.
  • the articles according to the invention are cigars or cigarillos provided with a natural cover sheet
  • they can be applied either by spraying the cover sheet with an aqueous solution of the glycoside or by dissolving the glycoside in the adhesive for the gluing between the surrounding and Cover sheet used glue.
  • the increased water solubility of the glycosides used according to the invention proves to be advantageous.
  • furaneyl glycosides release furaneol when they smoke, which due to its aroma is able to mask the aroma which is sometimes perceived as tobacco-foreign, for example ethyl vanillin, without reducing its positive effects, such as less irritating or stale smoke.
  • the figure below shows the decomposition curve of the ethyl vanillin maltoside used in smokable articles according to the invention, obtained with the aid of thermography (heating rate: 5 ° C./min).
  • Fig. 1 Thermogravimetry of ethylvanillin maltoside m / m 0 [%]
  • thermolytic cleavage of the glycosidic bond with the release of ethyl vanillin results in a theoretical mass loss of 34%.
  • a loss of mass of 31% in a temperature range of 160-260 ° C could be determined using the experimentally determined curve.
  • Example 3 Production and sensory evaluation of the sidestream smoke of a cigarette with ethylvanillinmaltoside
  • Filter cigarettes were used on a conventional cigarette machine in KS format (25 mm monoacetate filter with a 59 mm long tobacco rod, tobacco weight 630 mg, filter ventilation 40%, smoke data according to the ISO standard with a draft of 7.5 are 6 mg dry condensate and 0 , 6 mg smoke nicotine).
  • KS format 25 mm monoacetate filter with a 59 mm long tobacco rod, tobacco weight 630 mg, filter ventilation 40%, smoke data according to the ISO standard with a draft of 7.5 are 6 mg dry condensate and 0 , 6 mg smoke nicotine).
  • a commercially available American blend mixture was used as the tobacco mixture.
  • Commercially available cigarette paper (porosity 40 CU) was used to wrap the tobacco rod.
  • the ethylvanillin maltoside was applied to the paper using an application device from Kaymich, Sheffield, UK, during the manufacture of the tobacco rod on the cigarette machine.
  • Different doses of 0.15 and 0.6 mg glycoside per cigarette were tested.
  • a solution of the glycoside in warm water (temperature of 50 ° C) with a concentration of 75 g / 1 was added to the storage container of the device, which is equipped with a heater to keep the solution temperature at 40 ° C.
  • the application to the paper was carried out shortly before the formation of the strand, in that the paper was drilled with holes, i.e. with a metal block provided with nozzles.
  • the control of the dosing quantity was adjusted via the pump pressure in such a way that based on the weight of the cigarette paper (40 mg / cigarette) 5% by weight for the low dosage and 28% by weight of the glycoside solution on the wrapper for the high dosage were applied.
  • the sensory evaluation of the sidestream smoke of the test samples was carried out by a trained panel of smokers and non-smokers in comparison to similar cigarettes without flavoring glycoside in the cigarette paper.
  • the test samples were machine-smoked in a room of known size and defined equipment (eg 5 cigarettes in one Room with a volume of 20 m).
  • the evaluation was made immediately on the fresh smoke and also after 6 hours on the aged smoke.
  • the subjects had to indicate on a scaled questionnaire, among other things, how intense the smell of the aroma (here ethyl vanillin) and how strong the unpleasant properties associated with cigarette smoke, such as burning eyes, are perceptible.
  • the evaluation was carried out according to the statistical methods customary for sensory tests.
  • Example 4 Production and sensory evaluation of the sidestream smoke of a cigarette with ethylvanillin glucoside
  • cigarettes were produced and evaluated in accordance with Example 3, but which contained the conventional ethylvanin glucoside in different dosages of 0.1 and 0.4 mg / cigarette as a flavoring on the wrapping of the tobacco rod. Due to its poorer solubility in water and the higher dilution required, this glycoside was applied in a separate operation by brushing on the substance and then drying the paper.
  • Example 5 Production and sensory evaluation of the secondary flow smoke of cigarettes with a mixture of ethyl vanillin maltoside and furaneyl glucoside
  • Furaneyl glucoside ((2,5-dimethyl-4-oxo-dihydrofuran-3-yl) -ß-D-glucopyranoside) was first used according to a literature specification by R. R ⁇ SCHER et al. , in Phytochemistry 43 (1), 155 (1996).
  • filter cigarettes with a diameter of 7.9 mm and a total length of 84 mm were produced (21 mm monoacetate filter, 63 mm strand length, tobacco weight 750 mg, mixture type: American blend, filter ventilation 20%, smoke data according to ISO -Normal with a train count of 8.0: 11.8 mg dry condensate and 0.86 mg smoke nicotine).
  • a commercial cigarette paper was used as the strand wrapper, which was provided with a mixture of 0.15 mg of ethyl vanillin maltoside and 0.3 mg of furaneyl glucoside per cigarette.
  • Example 3 The cigarettes were evaluated as described in Example 3. The sidestream smoke was described as significantly more pleasant with a reduced irritating effect (fresh smoke) and less stale (aged smoke) compared to a commercially available comparison cigarette. No smell or taste unrelated to tobacco was found.
  • Example 6 Production and sensory evaluation of the sidestream smoke of cigarillos with a mixture of ethyl vanillin maltoside and furaneyl glucoside
  • Filter cigarillos with a diameter of 7.9 mm and an overall length of 84 mm were produced.
  • the cover sheet consisted of film tobacco produced by a paper process, which was impregnated with the mixture of ethyl vanillin maltoside and furaneyl glucoside mentioned in Example 5. This aroma mixture was applied during the production of the cover sheet in the size press.

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paper (AREA)
EP00987279A 1999-11-23 2000-11-22 Article aromatise a fumer Expired - Lifetime EP1231849B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19957486A DE19957486C2 (de) 1999-11-23 1999-11-23 Aromatisierte rauchbare Artikel
DE19957486 1999-11-23
PCT/EP2000/011610 WO2001037684A2 (fr) 1999-11-23 2000-11-22 Article aromatise a fumer

Publications (2)

Publication Number Publication Date
EP1231849A2 true EP1231849A2 (fr) 2002-08-21
EP1231849B1 EP1231849B1 (fr) 2005-06-08

Family

ID=7930781

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00987279A Expired - Lifetime EP1231849B1 (fr) 1999-11-23 2000-11-22 Article aromatise a fumer

Country Status (9)

Country Link
EP (1) EP1231849B1 (fr)
JP (1) JP2003530827A (fr)
AT (1) ATE297136T1 (fr)
AU (1) AU2358701A (fr)
DE (2) DE19957486C2 (fr)
ES (1) ES2240224T3 (fr)
HK (1) HK1048419B (fr)
TW (1) TW568754B (fr)
WO (1) WO2001037684A2 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014102070A1 (fr) * 2012-12-28 2014-07-03 Philip Morris Products S.A. Précurseurs d'arôme
WO2016156209A1 (fr) 2015-03-27 2016-10-06 Philip Morris Products S.A. Article de génération d'aérosol comportant un agent aromatique et une partie d'enveloppe de bout amovible
US20220240567A1 (en) * 2019-06-13 2022-08-04 Jt International S.A. Cigarillo or Cigar
CN110464043B (zh) * 2019-07-09 2022-01-11 河南中烟工业有限责任公司 用于加热不燃烧卷烟的清香香精及烟草薄片和不燃烧卷烟
KR102267982B1 (ko) * 2020-07-09 2021-06-21 주식회사 케이티앤지 바닐라 흡연물질 래퍼 및 이를 포함하는 흡연물품
WO2023001904A1 (fr) * 2021-07-20 2023-01-26 Jt International S.A. Matériau vaporisable destiné à être utilisé dans un dispositif de génération d'aérosol
KR102693877B1 (ko) 2021-09-23 2024-08-08 주식회사 케이티앤지 아로마 판상엽을 포함하는 흡연물품
KR102761267B1 (ko) 2021-12-28 2025-01-31 주식회사 케이티앤지 발삼계 향이 첨가된 흡연물질 래퍼 및 이를 포함하는 흡연물품

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Publication number Priority date Publication date Assignee Title
US3332428A (en) * 1964-10-01 1967-07-25 Liggett & Myers Tobacco Co Tobacco incorporating carbonate esters of flavorants
US4941486A (en) * 1986-02-10 1990-07-17 Dube Michael F Cigarette having sidestream aroma
GB8704196D0 (en) * 1987-02-23 1987-04-01 British American Tobacco Co Tobacco reconstitution
US4804002A (en) * 1987-05-29 1989-02-14 P. H. Glatfelter Company Tobacco product containing side stream smoke flavorant
DE3738491A1 (de) * 1987-11-12 1989-05-24 Efka Werke Kiehn Gmbh Fritz Umhuellung fuer eine formstabile tabakportion
US5137578A (en) * 1991-02-26 1992-08-11 Philip Morris Incorporated Smoking compositions containing a flavorant-release saccharide additive
ES2074330T3 (es) * 1991-10-05 1995-09-01 Quest Int Esteres de disacaridos del acido 3-metilpentanoico.
DE4244467C2 (de) * 1992-12-24 1996-11-14 Reemtsma H F & Ph Cigarette

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0137684A2 *

Also Published As

Publication number Publication date
HK1048419B (zh) 2005-09-23
JP2003530827A (ja) 2003-10-21
DE50010531D1 (de) 2005-07-14
TW568754B (en) 2004-01-01
AU2358701A (en) 2001-06-04
HK1048419A1 (en) 2003-04-04
EP1231849B1 (fr) 2005-06-08
DE19957486C2 (de) 2003-06-18
ES2240224T3 (es) 2005-10-16
DE19957486A1 (de) 2001-06-13
WO2001037684A2 (fr) 2001-05-31
ATE297136T1 (de) 2005-06-15
WO2001037684A3 (fr) 2001-11-22

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