DE1692938A1 - Process for influencing the taste properties of tobacco smoke - Google Patents

Process for influencing the taste properties of tobacco smoke

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Publication number
DE1692938A1
DE1692938A1 DE19661692938 DE1692938A DE1692938A1 DE 1692938 A1 DE1692938 A1 DE 1692938A1 DE 19661692938 DE19661692938 DE 19661692938 DE 1692938 A DE1692938 A DE 1692938A DE 1692938 A1 DE1692938 A1 DE 1692938A1
Authority
DE
Germany
Prior art keywords
tobacco
substances
added
methoxy
vinylbenzene
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.)
Pending
Application number
DE19661692938
Other languages
German (de)
Inventor
Auf Nichtnennung Antrag
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.)
HF and PhF Reemtsma GmbH and Co
Original Assignee
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 HF and PhF Reemtsma GmbH and Co filed Critical HF and PhF Reemtsma GmbH and Co
Publication of DE1692938A1 publication Critical patent/DE1692938A1/en
Pending legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18Treatment of tobacco products or tobacco substitutes
    • A24B15/28Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances

Description

H.F, & Ph.P. Reemtsma.Hamburg-Großflottbek,Parkstr.51H.F, & Ph.P. Reemtsma, Hamburg-Großflottbek, Parkstrasse 51

"Verfahren zur Beeinflussung der geschmacklichen Eigenschaften"Process for influencing the taste properties

des Tabakrauch.es"of tobacco smoke.es "

Die Erfindung betrifft ein Verfahren zur Beeinflussung der gegeschmacklichen Eigenschaften des Tabakrauches,welohea es ermöglicht, innerhalb weiter Grenzen die Geschmacksnote insbesondere einer Zigarettentabakmischung,gegebenenfalls auch einer Kunsttabakfolie oder einer neutralen selbst bei ihrem Verglimmen keine geschmacklich negativ wirksamen Komponenten entwickelnden Tragsubstanz zu beeinflussen.The invention relates to a method for influencing the palatable Properties of tobacco smoke, which makes it possible within wide limits the flavor note in particular of a cigarette tobacco mixture, possibly also one Artificial tobacco foil or a neutral film, even when it fades, does not develop any components that have a negative effect on the taste To influence supporting substance.

Es ist bereite vorgeschlagen worden(deutsche Patentschrift 1 131 580), Kunsttabakfasern dadurch herzustellen,daß eine vorgegebene Tabakmischung einer Sxtraktionsbehandlung-unter aufeinanderfolgender Extraktion der wasserlöslichen und Jer Alkohollöslichen Aromastoffe, unterzogen wird,durch welche sämtliche Aromastoffe gewonnen verden,aus diesen Stoffen einen Trockenextrakt herzustellen und diesen Extrakt einem aus Zellulose-oder Tylosematerial bestehenden Trägerstoff zuzumischen,worauf die Mischung zu Pasern vom Querschnitt der Naturfaser versponnen wird.It has already been proposed (German patent specification 1 131 580), Manufacture synthetic tobacco fibers in that a predetermined tobacco mixture an extraction treatment-under successive Extraction of water-soluble and alcohol-soluble flavorings, is subjected, through which all flavorings are obtained from to produce a dry extract of these substances and an extract made of cellulose or tylose material To mix in the carrier material, whereupon the mixture is made into strips of cross-section the natural fiber is spun.

Dieses bekannte Verfahren dient zu dem Zwecke,einen Kunsttabak herzustellen,welcher frei von den holzigen bzw.ZellulosebestandteilenThis known method is used for the purpose of producing an artificial tobacco, which free from the woody or cellulose components

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Neue Unterlagen (Art T% 1 Abs. 2 Nr. I Satz 3 de· Änderung»»*, v. 4.9.New documents (Art T% 1 Paragraph 2 No. I Sentence 3 de · Amendment »» *, v. 4.9.

des Tabaks ist,und nicht der planmäßigen Beeinflussung der Geschmackseigenschaften eines gegebenen Tabaks oder einer Tabakmischung.of tobacco is, and not the systematic manipulation of Taste characteristics of a given tobacco or tobacco blend.

Diese letztere Aufgabe liegt andererseits einem bekannten Verfahren(amerikanische Patentschrift 3147485) zugrunde,nach welchem einer Tabakmischung oder dem Material,aus welchem ein Zigarettenfilter besteht,bzw.dem Zigarettenpapier bestimmte organische Verbindungen zugesetzt werden sollen,um dadurch die unvermeidlichen auf Differenzen in der Beschaffenheit der Mischungskomponenten beruhenden Unterschiede einer gegebenen in der Zigarette enthaltenen Tabakmischung zu überblenden.On the other hand, this latter object is based on a known method (American patent specification 3147485) which a tobacco blend or the material from which a Cigarette filter exists or the cigarette paper determined Organic compounds should be added to avoid the inevitable differences in the nature of the Mixture components based differences of a given tobacco mixture contained in the cigarette to blend.

Gemäß der Erfindung wird erstmalig der Zusatz von aus Tabak isolierten Substanzen zur geschmacklichen Beeinflussung von Tabakmischungen vorgeschlagen,um die an sich vorhandene Wirkung der für das Aroma der Zigarette in erster Linie bestimmenden Mischungskomponenten und damit entweder das natürlicheAccording to the invention, for the first time, the addition of from tobacco isolated substances for influencing the taste of tobacco blends are proposed in order to reduce the existing effect which primarily determines the aroma of the cigarette Mixture components and thus either the natural one

Gesamtaroma der Zigarette bei gleichbleibendem Anteil dieser Mischungskomponenten zu verbessern,oder unter Umständen den Mengenanteil von teuren Komponenten der Tabakmischung herabzusetzen, ohne daß das durch diese Zusatzstoffe aufgefüllteTotal aroma of the cigarette with the same proportion of it To improve mixture components or, under certain circumstances, reduce the amount of expensive components in the tobacco mixture, without that being replenished by these additives

Aroma des Rauches nachteilig beeinflußt wird.Flavor of the smoke is adversely affected.

Die Aromastoffe,welche gemäß der Erfindung zugesetzt werden können,werden durch Untersuchung der betreffenden Tabakwasserdampfdestillate ermittelt.Sie können aus diesen Destillaten isoliert werden.Es ist aber auch möglich,diese Stoffe,nachdem ihre chemische Bestimmung durch Untersuchung der TabakwasserdampfDestillate erfolgt ist,synthetisch herzustellen,ohne daß dann also für ihre Gewinnung von ifaturtabak ausgegangen werden muß.The flavoring substances which are added according to the invention can be determined by examining the tobacco steam distillates in question They can be isolated from these distillates, but it is also possible to use these substances after their chemical determination by examining the tobacco water vapor distillates has taken place to produce synthetically, without then starting out from ifatur tobacco for their production got to.

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Biese Stoffe werden in jeweils zweckentsprechenden Mengen,die innerhalb verhältnismäßig weiter Grenzen schwanken können,und je nach ihrer Zusammensetzung 5-500 Teile auf 1 Million(ppm) betragen können,zugesetzt.These substances are used in appropriate amounts may fluctuate within relatively wide limits, and depending on their composition 5-500 parts to 1 million (ppm) can be added.

Als eine erste Gruppe von den Toraussetzungen des neuen Verfahrens entsprechenden,teilweise also solche neuen Stoffen, deren Vorhandensein im Tabak und deren Wirkung auf das Aroma des Tabakrauchs festgestellt wurden,seien die VinyTbenzole,die in der 3.4.-Stellung durch Hydroxygruppen,Methoxygruppen und die Methylendloxygruppen disubstituiert sind,sowie die,deren Vinylgruppe zu der entsprechenden sekundären Alkoholgruppe hydratisiert worden sind,insbesondere die folgenden Verbindungen zu nennen:As a first group of the goal suspensions of the new procedure corresponding, in some cases such new substances, their presence in tobacco and their effect on the aroma of tobacco smoke were found to be the VinyTbenzenes, the in the 3.4.-position by hydroxyl groups, methoxy groups and the methylenedoxy groups are disubstituted, as well as those whose Vinyl group have been hydrated to the corresponding secondary alcohol group, particularly the following compounds to call:

1. 1-Hydro3cy-2-methoxy-4-vinylbenzol1. 1-Hydro3cy-2-methoxy-4-vinylbenzene

2. 1-Hydroxy-2-methoxy-5-viny!benzol2. 1-Hydroxy-2-methoxy-5-vinyl benzene

3. 1.2.-Dimethoxy-4-Vinylbenzol3. 1.2.-Dimethoxy-4-vinylbenzene

4. 1.2.-Methylen-dioxy-4-viny!benzol4. 1.2.-Methylen-dioxy-4-vinylbenzene

5. 4-Hydroxy-5-methoxy-a-phenaethylalkohol5. 4-Hydroxy-5-methoxy-a-phenaethyl alcohol

Diese Stoffe werden dem Tabak für sich oder in Mischung in anteiligen Mengen von zwischen 5 und 500 ppm,vorzugsweise 10 bis 100 ppm zugesetzt.These substances are used alone or in a mixture in the tobacco proportional amounts of between 5 and 500 ppm, preferably 10 to 100 ppm, are added.

Eine zweite aus dem Wasserdampfdestillat .Isolierbare Gruppe Ton Substanzen,die das Aroma des Tabakrauches mitbestimmen, umfaßt die folgenden Verbindungen:A second group that can be isolated from the steam distillate Clay substances that determine the aroma of tobacco smoke, includes the following compounds:

1. 4 2·.6·.6'-Trimethylcyelonexanon-(4f)-yliden-(1r)-buten-(2) sowie der entsprechende Alkohol1. 4 2 · .6 · .6'-Trimethylcyelonexanone- (4 f ) -ylidene- (1 r ) -butene- (2) and the corresponding alcohol

2. 4 2·.6·.6·-Trimethylcyclohexen-C2«)-on-(4*)-yl-(1')-buten-(2) sowie der entsprechende Alkohol2. 4 2 · .6 · .6 · -Trimethylcyclohexene-C2 «) - on- (4 *) - yl- (1 ') - buten- (2) as well as the corresponding alcohol

209812/1263209812/1263

3. 4 2·.6'.6·-Trimethylcyclohexen-(2·)-on-(4')-yliden-(1·)-buten-(2) sowie der entsprechende Alkohol3. 4 2 · .6'.6 · -Trimethylcyclohexen- (2 ·) -one- (4 ') -yliden- (1 ·) -butene- (2) as well as the corresponding alcohol

4. 4 2'.6l.6l-Trimethylcyclohexen-(2')-on-(4l)-yliden-(11)-butan sowie der entsprechende Alkohol4. 4 2'.6 l .6 l -Trimethylcyclohexen- (2 ') -one- (4 l ) -ylidene- (1 1 ) -butane and the corresponding alcohol

5. 4 2».6·.6f-Trimethylcyclohexanon-(4')-yl-(1')-buten-(2) sowie der entsprechende Alkohol5. 4 2 ».6 · .6 f -trimethylcyclohexanon- (4 ') - yl- (1') - butene (2) and the corresponding alcohol

6. 4 2l.6'.6'-Trimethylcyclohexen-(2l)-on-(4t)-yl-(1l)-"butan sowie der entsprechende Alkohol6. 4 2 l .6'.6'-Trimethylcyclohexen- (2 l ) -one- (4 t ) -yl- (1 l ) - "butane and the corresponding alcohol

7. 4 2·.6'.6'-Trimethylcyclohexanon-(4')-yliden-(1')-butan sowie der entsprechende Alkohol7. 4 2 · .6'.6'-trimethylcyclohexanon- (4 ') - ylidene- (1') - butane as well as the corresponding alcohol

a. 4 2i.6l.6l-Trimethylhexen-(2l)-on-(4f)-yl-(11)-butanol-(2) a. 4 2 i .6 l .6 l -Trimethylhexen- (2 l ) -one- (4 f ) -yl- (1 1 ) -butanol- (2)

9. 4 2'.6'.6l-Trimethylcyclohexen-(2l)-on-(4l)-yl-(1l) -butanol-(2)9. 4 2'.6'.6 l -Trimethylcyclohexen- (2 l ) -one- (4 l ) -yl- (1 l ) -butanol- (2)

IO; 4 2l.6l.6l-Trimethylcyclohexen-(2'7-on-(4t)-yl-(1')-"buten-IO; 4 2 l .6 l .6 l -Trimethylcyclohexen- (2'7-one- (4 t ) -yl- (1 ') - "buten-

11. 4 2t.6l.6t-Irimethylcyclohexen-(2l)-on-(4l)-yliden-(11)-butanon-(3). 11. 4 2 t .6 l .6 t -Irimethylcyclohexen- (2 l ) -one- (4 l ) -ylidene- (1 1 ) -butanone- (3).

12. 4 2·.6·.6'-Trimethylcyclohexanon-(4')-yl-(1')-butanon-(3) und deren Di- und Tetrahydroderivate.12. 4 2 · .6 · .6'-Trimethylcyclohexanon- (4 ') - yl- (1') - butanone- (3) and their di- and tetrahydro derivatives.

Diese Stoffgruppe ist bereits in kleineren Mengen von Größenordnungsmäßig 2 bis 120 ppm,die dem Tabak zugesetzt werden,im Sinne der Zielsetzung des neuen Verfahrens wirksam.This group of substances is already present in smaller amounts of the order of 2 to 120 ppm, which are added to the tobacco Effective in terms of the objective of the new procedure.

m * βm * β

• *• *

Die Isolierung dieser Stoffe aus den Wasserdampfdestillaten erfolgt nach den hierfür üblichen Methoden der organischen Chemie.These substances are isolated from the steam distillates using the organic methods customary for this purpose Chemistry.

Durch die Erfindung werden neue Möglichkeiten sowohl für die Beeinflussung der geschmacklichen Eigenschaften des Ta~bakrauch.es wie gegebenenfalls auch in wirtschaftlicher Hinsicht für dieThe invention opens up new possibilities for influencing the taste properties of the tobacco smoke as if necessary also in economic terms for the

Terbilligung von teuren Mischungskomponenten und Erzeugung derDiscounting of expensive mixture components and production of the

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sonst auf diese zurückgehenden Nuancen der geschmacklichen Eigenschaften durch die erfindungsgemäß zuzusetzenden tabakeigenen Stoffe eröffnet.otherwise due to these nuances of the taste properties due to the tobacco inherent to be added according to the invention Fabrics opened.

Patentansprüche: Patent claims :

- 6 209812/1263 - 6 209812/1263

Claims (6)

Patentansprüche:Patent claims: 1. Verfahren zur Beeinflussung der geschmacklichen Eigenschaften des Tabakrauches von Zigaretten durch Zusatz von aromatisierenden Substanzen zu der Tabakmischung, dadurch gekennzeichnet ,daß dem Tabak bestimmte aromatisierende,tabak4igene Stoffe zugesetzt werden.1. Process for influencing the taste properties the tobacco smoke from cigarettes by adding flavoring substances to the tobacco mixture, characterized in that the Certain flavoring substances inherent in tobacco are added to tobacco will. 2. Verfahren nach Anspruch 1,dadurch gekennzeichnet ,daß durch die zugesetzten aromatisierenden Stoffe eine oder mehrere Komponenten der Tabakmischung, die die gleichen Aromastoffe entwickeln, ganz oder teilweise ersetzt werden.2. The method according to claim 1, characterized in that the added flavoring Substances one or more components of the tobacco mixture that develop the same flavoring substances, in whole or in part be replaced. 3.Verfahren nach Anspruch 1 und 2,d adurch gekennzeichnet ,daß als aromatieierende Stoffe Vinylbenzole, die in der 3.4-Stellung durch Hydroxygruppen,Methoxygruppen und die Methylendioxygruppen disubstituiert sind,zugesetzt werden.3. The method according to claim 1 and 2, characterized by d that as aromatizing substances vinylbenzenes, those in the 3,4-position by hydroxyl groups, methoxy groups and the methylenedioxy groups are disubstituted will. 4. Verfahren nach Anspruch ?,d adurch gekennzeich η e t,daß als aromatisierende Stoffe einer odor mehrere der folgenden Stoffe4. The method according to claim?, D adurch marked η e t that as flavoring substances one odor several of the following substances 1. I-Hydroxy^-Methoxy^-Vinylbenzol1. I-Hydroxy ^ -Methoxy ^ -Vinylbenzene 2. 1-Hydroxy-2-Methoxy-5-VinyTbenzol/2. 1-Hydroxy-2-Methoxy-5-VinyTbenzene / 3. 1.2-Dimethoxy-4-Vinylbenzol3. 1,2-dimethoxy-4-vinylbenzene 4. 1.2-Methylen-Dioxy-4~Vinylbenzol4. 1,2-methylene-dioxy-4-vinylbenzene 5. 4-Hydroxy-5-Methoxy- -Phenäthyl-Alkohol5. 4-Hydroxy-5-methoxy-phenethyl alcohol zugesetzt werden.can be added. 5. Verfahren nach Anspruch 1 bis 4, dadurch gekennzeichne t,daß die zugesetzten Stoffe durch Isolierung aus dem Tabakwasserdampfdestillat hergestellt werden.5. The method according to claim 1 to 4, characterized t that the added substances are produced by isolation from the tobacco steam distillate. 209812/1263 Neue, Unterlagen (Art ? 11 Abi. 2 Nr. 1 s«tz 3 m' h^j^bi 19. \w\ 209812/1263 New, documents (Art ? 11 Abi. 2 No. 1 s «tz 3 m 'h ^ j ^ bi 1 9. \ w \ 6. Verfahren nach Anspruch 1 bis 5»d adurcb. gekennzeichne t,daß die Zusatzstoffe synthetisch hergestellt werden.6. The method according to claim 1 to 5 »d adurcb. marked t that the additives are produced synthetically. 209812/1263209812/1263
DE19661692938 1966-03-05 1966-03-05 Process for influencing the taste properties of tobacco smoke Pending DE1692938A1 (en)

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BE (1) BE694958A (en)
CH (1) CH491610A (en)
DE (1) DE1692938A1 (en)
GB (2) GB1175441A (en)
LU (1) LU53121A1 (en)
NL (1) NL6703164A (en)
NO (1) NO118357B (en)
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US3047433A (en) * 1961-10-19 1962-07-31 Philip Morris Inc Use of diels-alder adducts as tobacco additives
GB989703A (en) * 1963-04-29 1965-04-22 British American Tobacco Co Improvements relating to the processing of smoking tobacco
US3174485A (en) * 1963-05-23 1965-03-23 Brown & Williamson Tobacco Organoleptically improved tobacco product
US3298378A (en) * 1964-01-30 1967-01-17 Kimberly Clark Co Method of making a tobacco product

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US7462727B2 (en) 2003-07-25 2008-12-09 Basf Aktiengesellschaft Multimetal oxide containing silver, vanadium and a promoter metal and use thereof

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CH491610A (en) 1970-06-15
GB1175441A (en) 1969-12-23
NL6703164A (en) 1967-09-06
BE694958A (en) 1967-08-14
SE343465B (en) 1972-03-13
LU53121A1 (en) 1967-05-03
US3476118A (en) 1969-11-04
GB1175442A (en) 1969-12-23
NO118357B (en) 1969-12-15

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