Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3920026 A
Publication typeGrant
Publication dateNov 18, 1975
Filing dateMar 7, 1972
Priority dateMar 7, 1972
Also published asDE2310781A1, DE2310781B2
Publication numberUS 3920026 A, US 3920026A, US-A-3920026, US3920026 A, US3920026A
InventorsGalloway William Dwight, Kallianos Andrew G, Warfield Albert H
Original AssigneeLiggett & Myers Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Tobacco with flavor enhancer
US 3920026 A
Abstract
This disclosure is directed to a tobacco flavor enhancer from the reaction of valine with a sugar, other hydroxycarbonyl compound, or dicarbonyl compound. The reagents are heated in the presence of a solvent, optionally including a catalyst in the form of a flavanoid or hydroxyacid. The reaction mixture can be used directly in tobacco compositions, or can be stripped, and either or both the volatile and nonvolatile portion can be used in tobacco compositions.
Images(4)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

, United States Patent [191 Warfield et a1.

TOBACCO WITH FLAVOR ENHANCER Liggett & Myers Incorporated, Durham, NC.

Filed: Mar. 7, 1972 Appl. No.: 232,526

Assignee:

U.S. Cl 131/17 R; 131/144; 260/209 R lnt. Cl. A24B 03/12; A24B 15/04 Field of Search 260/209 R, 210 R, 21 1 R,

260/21l.5 R; 131/2, 17'R,144

References Cited UNITED STATES PATENTS 6/1955 Ruskins 260/21 1.5 R 11/1956 King 260/21 1.5 R

[ Nov. 18, 1975 2,785.152 3/1957 Jonas 260/21l.5 R 2,805,219 9/1957 Kagan et al..... 260/211 R 3,089,869 5/1963 Mauvernay 260/21 1.5 R 3,304.184 2/1967 Wiseblatt et a1. 131/144 UX 3,722.516 3/1973 Suwa et a1. 131/144 X Primary Examiner-Melvin D. Rein Attorney, Agent, or Firm-Kenyon & Kenyon [57] ABSTRACT This disclosure is directed to a tobacco flavor enhancer from the reaction of valine with a sugar, other hydroxycarbonyl compound, or dicarbonyl compound. The reagents are heated in the presence of a solvent, optionally including a catalyst in the form of a flavanoid or hydroxyacid. The reaction mixture can be used directly in tobacco compositions, or can be stripped, and either or both the volatile and nonvolatile portion can be used in tobacco compositions.

l4 (Jaims, No Drawings 1 TOBACCO WITH F'LAvoR ENHANCER I BACKGROUNDOF THE INVENTION Numerous workers have investigated the reaction between amino acids and carbonyl compounds or sugars. This reaction is known as nonenzymatic browning and has been studied largely because of the ultimate production of brown pigments in foods. An intermediate or side reaction results in the production of volatile materials and certain less volatile'residues which have not been as extensively studied. However, it has been appreciated that these materials produce interesting flavors and aromas.

The production, from amino acids and carbonyl compounds or sugars, of subst ances with desirable flavors and aromas, and the methods of using these substances, have raised several problems. For example, the flavors and aromas produced may not be desirable, or desirable products may be masked by the presence of other products. In addition, desirable products may be destroyed if maintained at elevated temperatures or upon reaction with other components. Furthermore, important differences may exist in the suitability of the final product depending on the particular amino acid used in the procedure.

Japanese Patent No. 9,239/71 discloses the preparation of specific condensates of sugars with amino acids, which are added to tobacco products. As the tobacco is smoked the condensates are thermally decomposed and a fragrance is released.

It is an object of this invention to provide an improved method for the reaction of amino acids and sugars or other carbonyl compounds. A further object is the production of useful substances from the reaction of an amino acid, preferably valine, and a sugar or carbonyl compound, to provide tobacco compositions incorporating such substances. These and other objects are set forth, in great detail in the accompanying detailed specification.

SUMMARY OF THE INVENTION This invention is directed to a tobacco composition cifically it relates to the reaction of an amino acid with a sugar or carbonyl compound at an elevated temperature in the presence of a solvent. The reaction may be carried out with or without the inclusion of a substance acting as a catalyst, which has the effect of enhancing the aroma and flavor of the tobacco to which the mixture is applied. I

The amino acid employed in the process of this invention is primarily valine, but mixtures of amino acids such as those derived by hydrolysis of proteins with a high valine content may also be used. Either optical isomer of valine is suitable in this invention. V

The reagent with which the amino acid is reacted in the process of this invention may be a sugar or other carbonyl compound. Preferred sugars are pentoses such as xylose, and hexoses such as glucose or fructose. Disaccharides such as maltose, or higher polysaccharides such as rafflnose may be used, but reducing sugars are preferred due to the shorter times and lower temperatures necessary for, running the reactions. Other carbonyl compounds which may be used in place of sugars are, for example, hydroxyketones, such asdihy- 2 droxyacetone, or dicarbonyl compounds such as pyruvaldehyde.

The catalyst used-in the method of the invention may be a flavanoid, such as quercetin or rutin, or a hydroxyacid,.such as ascorbic acid.

The solvent used for carrying out the reactions specified according to this invention may be any convenient liquid, such as polyhydroxylic solvents, mineral or vegetable oils, or water. However, polyhydroxylic solvents such as glycerol or propylene glycol are preferred, since their boiling points are in the temperature range useful in the method of the invention, and they are compatible with existing methods of tobacco processing.

In the method of this invention the amino acid and carbonyl compound are added to the solvent, the catalyst added, and the mixture heated to lO0-200C (preferably l20200C) for 0.5 to 5 hours, depending on the combination of materials used. A condenser may be employed, but is not always necessary. The re-;

action is usually complete when bubbling ceases; The molar ratio of amino acid tocarbonyl compound can be from about I 10.5-10, with a ratio of l:4-5 being optimum in most cases. The weight ratio of amino acid to the solvent used may be about 111-200, but ratios 'of' 1110- are preferred. Weight ratios of catalyst to amino acid may be 0-100 percent, but levels of 0.510 percent are preferred.

The preferred reaction temperature for reducing sugars, hydroxycarbonyl compounds or dicarbonyl com-' pounds is l50160. This range of temperatures usually results in reaction times of 45 to 60- minutes. Higher temperatures tend to produce objectionable, burnt aromas, and lower temperatures produce inconveniently long reaction times. In the case of nonreducing sugars, such as sucrose or rafflnose, reaction rates are much lower, and higher temperatures, longer reaction times, or a combination of these must be employed.

The reaction mixtures prepared according to this invention are useful in tobacco as such, or can be further treated by passing the solution slowly through a steamjacketed column under vacuum, trapping the volatile materials in cold traps, and collecting the'solution containing the nonvolatiles separately. This is known as the stripping operation.

The volatile portion of the reaction mixture is useful in improving the fragrance of tobacco and tobacco products, and in reducing throat irritation.

The nonvolatile portion of the reaction mixture is useful especially in poorer tobaccos or those which have been aged for shorter than normal periods of time. The usefulness of this material derives principally from its ability to reduce or mask the green-grassy taste associated with these tobaccos. Another property of the nonvolatile part of the reaction mixtures is the enhancement of desirable flavor notes of the particular tobacco to which it is applied, while suppressing undesirable harsh, or irritating properties.

In most of the reaction mixtures prepared according to this invention, the stripping operation is not absolutely necessary, especially if some of the more volatile materials are allowed to escape during the reaction. Nearly all of the desirable properties produced during smoking tobacco products containing these mixtures are attributable to the nonvolatile portion.

In addition to stripping, the reaction mixture may be improved by extraction with an immiscible solvent,

3 such as ether, methyl isobutyl ketone, or isobutyl acetate. This extraction is usually done after the mixture has been diluted somewhat with water, and may be carried out as either a batch or continuous process.

Much the same effect as extraction can be accom plished by subjecting the total reaction mixture to dialysis, using regenerated cellulose, or other suitable membrane. This process removes all the low molecular weight materials, resulting in an aqueous solution of browning pigments, which may be isolated by evaporating the water. These pigments possess all of the desirable properties of the total reaction mixture when applied to tobacco at appropriate levels. Thus, according to the method of this invention, it is possible to preferentially remove the undesirable intermediates, and add only those materials which are desirable for tobacco products.

The above properties of the reaction mixtures are also applicable in the case of reconstituted tobacco productsv Undesirable taste properties of these tobaccos are often encountered, which are related to the green taste of poor tobaccos, or the papery taste of stem material. The additive has the effect of masking these undesirable tastes, reducing throat irritation and sting, and enhancing natural tobacco taste.

In practice, the unstripped reaction mixture can be applied to tobacco in an amount equivalent to about 0.001 to 2.0 percent, based on the amount of amino acid used at the beginning of the reaction and the 4 The following specific examples serve to illustrate the procedure used in preparing the flavorants and flavor enhancers described in this disclosure.

5 EXAMPLE 1 A mixture of 1 g DL-valine, 7.2 g D-glucose, 100 mg rutin and 100 ml glycerol was heated to 160 for min. An odor of chocolate with burnt sugar and peanut undertones was noticed on cooling.

EXAMPLE II A mixture of 20 g L-valine. 2 g rutin, and 24 g D- glucose was added to 200 ml glycerol and heated to 160 for 1 hour, using a reflux condenser to prevent loss of volatiles. When cooling, the mixture was passed slowly through a stripper which consisted of a steamheated glass coil connected in series to a receiving flask, two liquid air-cooled traps, and a vacuum pump. The volatile materials stripped off in the coil were trapped, and then washed out of the traps with ether. After separating and reextracting the water present in the traps, the combined ether solutions were dried over sodium sulfate, and a total solids determination showed that the volatiles weighed 470 mg.

The nonvolatile portion of the reaction, which included the glycol solvent, had a slightodor of chocolate, and weighed 253 g.

The following additional samples (Table I) serve to illustrate the variations of the invention that produce amount of solvent employed. The exact percentage de- 30 useful flavorants and flavor enhancers.

TABLE 1 Ex. Wt. of Carbonyl Wt. Vol. Reaction No. Valine (g) Cmpd. WLtg) Catalyst (g) Solvent (ml) Conditions Aroma Description 111 1.0 D-Glucose 1.5 Glycerol 7 160l45 min Parched corn with chocolate undertones.

IV 1.0 D-Glucose 1.5 Rutin 1.0 Glycerol 7 160/45 min Chocolate-like, with sharp parched corn notes.

V 1.0 D-Maltose 2.4 Glycerol 10 160l45 min Pleasant, mild-chocolate.

V1 1.0 D-Raffinose 1.2 Glycerol 10 155/80 min Weak chocolate.

Reaction incomplete.

V11 10 D-Sucrose 1.5 Rutin 0.1 Glycerol l0 155l80 min Chocolate, Reaction incomplete.

V111 1.0 D-Fructose 1.5 Glycerol 160l45 min Strong, full flavored,

chocolate; peanut-like note.

IX 1.0 Dihydroxy- 1.54 Glycerol 10 /60 min Fairly good chocolate.

acetone with sour green notes.

K 1.0 Pyruvaldehyde 4.1 Glycerol 10 150/60 min Sweet, pleasant chocolate.

Xl 10.0 D-Glucose 15.0 Rutin 0.1 Propylene 100 /60 min Fruitychocolate.

glycol X11 10.0 D-Glucose 15.0 Rutin 0.1 d-Sorbitol 120g l60l45 min Pungent, acid-like.

Xlll 10.0 D-G|ucose 15.0 Quercetin 0.1 Glycerol 100 160l45 min Fruity-green chocolate.

.XlV 10.0 D-Glucose 15.0 Ascorbic 0 1 Glycerol 100 160/45 min Pleasant green-chocolate.

Acid

30% Aqueous solution.

pends on the effect desired. The material which has been stripped of volatiles is also applied at these levels, but usually somewhat higher than the unstripped material. The volatile portion which collects in the traps during the stripping operation is useful at about 0.001 to 0.05 percent, based on its total solids content, which is determined while in ether solution.

The methods of applying these materials are known to those practiced in the art, but basically consist of spraying or dipping, preferably theformer. One very convenient method is the incorporation of the material into the casing formulation and applying during the customary casing operation. Another method is to mix the material with ethanol or other suitable solvent and to incorporate into the top-dressing, which is then applied in the normal manner.

EXAMPLE XV A mixture of 20 g DL-valine, 157 g D-glucose, 0.20 g rutin and 600 g glycerol was heated to 160 in an open reaction vessel, and maintained at this temperature for 1 hour, with continuous stirring. The mixture, on cooling, was diluted with 500 ml water and extracted with three 200 ml portions of ether. The aqueous-glycerol solution was heated on a steam bath for 2 hours to remove remaining traces of ether. The resulting solution had a specific gravity of 1.213. Dialysis of an aliquot against distilled water, using regenerated cellulose tubing as the semipermeable membrane, showed that 18.6 g of browning pigments were contained in the total solution.

Specific examples ofincorporating the reaction products from the above examples into tobacco products are as follows:

EXAMPLE XVI EXAMPLE XVII The volatile portion from Example II was diluted to 50 ml with 95% ethanol. A 0.1 ml aliquot of this solution was diluted to ml with 50% aqueous alcohol and sprayed onto 100 g of low grade Virginia tobacco. Cigarettes made from this tobacco had an accented Virginia tobacco taste.

EXAMPLE XVIII A solution of 0.05 g of the nonvolatile (stripped) portion from Example II, in 1 ml of 50% aqueous alcohol, was sprayed onto 100 g of low grade Virginia tobacco. Cigarettes made from this tobacco exhibited a reduction of the green-grassy taste noticed in the control cigarettes. The mixture also produced a rounding of the flavor and a much smoother smoke.

EXAMPLE XIX The procedure of Example XVIII was repeated using a low grade Burley tobacco. The cigarettes made from this tobacco displayed a reduction in impact and sharpness when compared to a control, and the desirable burley fragrance was enhanced.

EXAMPLE XX The procedure of Example XVIII was repeated using reconstituted tobacco. The cigarettes prepared from this tobacco, when compared to control cigarettes, had

a reduced oak-leaf taste, and a sweet, spice-like flavor.

EXAMPLE XXI The procedure of Example XX was repeated, except that a solution of 0.1 g of the nonvolatile portion in 1 ml 50% aqueous alcohol was used. Cigarettes prepared from this tobacco exhibited enhanced tobacco taste, along with reduced throat irritation and mouth pepperiness.

EXAMPLE XXII A solution of 0.1 g of the mixture prepared as set forth in Example XI, in 2 ml 50% aqueous alcohol, was sprayed onto I00 g of a cased and cut commercial blend of tobaccos and evaluated as in Example XVI. The smoke from cigarettes thus prepared showed a noticeable reduction in impact and amplitude, and a slight reduction in the oak-leaf taste associated with reconstituted tobacco. The flavor showed less pepperiness and was somewhat sour.

EXAMPLE xxm A solution of 0.1 g of the mixture prepared as set forth in Example XIV, in 2 ml 50% aqueous alcohol, was sprayed onto g of a commercial blend of tobaccos and evaluated as in Example XVI. The cigarettes produced a slightly lower impact and amplitude of flavor than the untreated control, with an increase in sour-green notes.

EXAMPLE XXIV A solution of 12 mg of the pigments isolated as described in Example XV, in 2 ml of a 50% aqueous alcohol solution, was sprayed onto 100 g of unflavored cut tobacco, and cigarettes prepared accordingly. The smoke produced by these cigarettes was described by the flavor panel as having a lesser degree of harshness and irritation than a similarly prepared control, with better balance, and more sweet taste and tobacco fragrance.

This invention has been described in terms of specific embodiments set forth in detail. Alternative embodiments will be apparent to those skilled in the art in view of this disclosure, and accordingly such modifications are to be contemplated within the spirit of the invention as disclosed and claimed herein.

We claim:

1. A tobacco composition comprising tobacco and a minor amount of a flavor enhancer wherein the enhancer is a non-volatile solution of browning pigments made by heating between about l20 200C 21 reaction mixture containing a solvent, valine and a carbonyl compound selected from the group consisting of a sugar, dihydroxy acetone and pyruvaldehyde.

2. The composition of claim 1 wherein the solvent is selected from the group consisting of glycerol and propylene glycol.

3. The composition of claim 1 wherein the reaction mixture contains a catalyst.

4. The composition of claim 3 wherein the catalyst is selected from the group consisting of rutin, quercetin, and ascorbic acid.

5. A tobacco composition comprising tobacco and a minor amount ofa flavor enhancer; said enhancer comprising the browning pigments separated from the reaction product of a mixture heated to between about C and 200C of a solvent, valine and a carbonyl compound selected from the group consisting of sugar, dihydroxy acetone and pyruvaldehyde.

6. The composition of claim 5 wherein the solvent is selected from the group consisting of glycerol and propylene glycol.

7. The composition of claim 5 which further comprises a catalyst.

8. The catalyst of claim 6 selected from the group consisting of rutin, guercitin and ascorbic acid.

9. The composition of claim 1 wherein the sugar is a pentose or hexose.

10. The composition of claim 5 wherein the sugar is a pentose or hexose.

11. The composition of claim 1 wherein the sugar is a reducing sugar.

12. The composition of claim 1 1 wherein the temperature is between about l50C and 160C.

13. The composition of claim 5 wherein the sugar is a reducing sugar.

14. The composition of claim 13 wherein the temperature is between about C and l60C.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2710860 *Oct 10, 1947Jun 14, 1955Physiclogical Chemicals CompanNikethamide adenylate
US2772168 *Nov 28, 1951Nov 27, 1956Colgate Palmolive CoFermentable carbohydrate food products
US2785152 *Apr 13, 1953Mar 12, 1957Nat Dairy Prod CorpAldonyl amides of amino acid esters
US2805219 *Sep 9, 1954Sep 3, 1957Upjohn CoResolution of racemic alpha-hydroxy-beta, beta-dimethyl-gamma-butyrolactone
US3089869 *Mar 30, 1960May 14, 1963Lab D Analyses Et De Rech S ROrganic acid esters of adenosine phosphates
US3304184 *Jun 7, 1966Feb 14, 1967Research CorpBreadstuff flavoring compositions and methods of making them
US3722516 *Feb 9, 1971Mar 27, 1973Ja Monopoly Corp And Tanabe SeSmoking tobacco product and method of making the same
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4286606 *Jun 18, 1979Sep 1, 1981Philip Morris IncorporatedTobacco flavorants
US4306577 *Apr 12, 1979Dec 22, 1981Philip Morris IncorporatedReaction flavors for smoking products
US4537204 *Jan 10, 1983Aug 27, 1985Fabriques De Tabac Reunies S.A.Method of tobacco treatment to produce flavors
US5962662 *Mar 19, 1992Oct 5, 1999R.J. Reynolds Tobacco CompanyMethod for producing a flavorful and aromatic composition for use in smoking articles
US6030462 *Oct 22, 1998Feb 29, 2000R.J. Reynolds Tobacco CompanySmoking article having increased amino acid content
US6325860Feb 15, 2000Dec 4, 2001R. J. Reynolds Tobacco CompanyMethod of providing flavorful and aromatic compounds in absence of reducing sugars
US6428624Jul 19, 2001Aug 6, 2002R. J. Reynolds Tobacco Co.Method of providing flavorful and aromatic compounds
US6440223Feb 15, 2000Aug 27, 2002R. J. Reynolds Tobacco Co.Smoking article containing heat activatable flavorant-generating material
US6499489May 12, 2000Dec 31, 2002R. J. Reynolds Tobacco CompanyTobacco-based cooked casing formulation
US6695924Jul 25, 2000Feb 24, 2004Michael Francis DubeMethod of improving flavor in smoking article
CN102754913A *Jul 31, 2012Oct 31, 2012龙功运Blended additive for atomizing smoke after heating tobacco, using method thereof and tobacco composite thereof
CN104026729A *Jun 25, 2014Sep 10, 2014湖南中烟工业有限责任公司Electronic cigarette liquid with scorch aroma
CN104026729B *Jun 25, 2014Nov 4, 2015湖南中烟工业有限责任公司一种具有焦香香气的电子烟液
DE3722129A1 *Jul 3, 1987Jan 12, 1989Bat Cigarettenfab GmbhProcess for the continuous production of aroma substances, in particular tobacco aroma substances
EP0056073A1 *Sep 18, 1981Jul 21, 1982Fabriques De Tabac Reunies S.A.Process for the preparation of tobacco and tobacco prepared by this process
EP0056268A1 *Jan 9, 1982Jul 21, 1982Fabriques De Tabac Reunies S.A.Process for the preparation of tobacco
Classifications
U.S. Classification131/276, 536/18.7
International ClassificationA24B3/00, A24B3/12, A24B15/30, A23L1/226, A24B15/00
Cooperative ClassificationA24B15/306, A24B15/305
European ClassificationA24B15/30E, A24B15/30E2
Legal Events
DateCodeEventDescription
Mar 18, 1999ASAssignment
Owner name: BANKERS TRUST COMPANY, NEW YORK
Free format text: TERMINATION AND RELEASE OF SECURITY INTEREST;ASSIGNOR:LIGGETT GROUP, INC.;REEL/FRAME:009817/0266
Effective date: 19990301
Mar 18, 1999AS99Other assignments
Free format text: BANKERS TRUST COMPANY FOUR ALBANY STREET NEW YORK, NEW YORK 10006 * LIGGETT GROUP, INC. : 19990301 OTHER CASES: NONE; TERMINATION AND RELEASE OF SECURITY INTEREST
Apr 8, 1992AS06Security interest
Owner name: BANKERS TRUST COMPANY
Effective date: 19920214
Owner name: FIRST UNION NATIONAL BANK OF NORTH CAROLINA
Owner name: LIGGETT GROUP INC.
Apr 8, 1992ASAssignment
Owner name: BANKERS TRUST COMPANY
Owner name: FIRST UNION NATIONAL BANK OF NORTH CAROLINA
Free format text: SECURITY INTEREST;ASSIGNOR:LIGGETT GROUP INC.;REEL/FRAME:006107/0141
Owner name: LIGGETT GROUP INC. F/K/A LIGGETT & MYERS TOBACCO
Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLATERAL AGENT;REEL/FRAME:006107/0151
Effective date: 19920214
Apr 8, 1992AS17Release by secured party
Owner name: LIGGETT GROUP INC. F/K/A LIGGETT & MYERS TOBACCO C
Effective date: 19920214
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT
Jun 12, 1991AS99Other assignments
Free format text: BROOKE GROUP LTD., A DE CORPORATION; UNITED STATES TRUST COMPANY OF NEW YORK * LIGGETT GROUP INC., A DE CORPORATION : 19910610 OTHER CASES: NONE; THIS DOCUMENT IS AMENDING AND RESTATING THE TERMS OF THE LOA
Jun 12, 1991ASAssignment
Owner name: BROOKE GROUP LTD., A DE CORPORATION
Free format text: THIS DOCUMENT IS AMENDING AND RESTATING THE TERMS OF THE LOAN AGREEMENT DATED MARCH 6, 1987.;ASSIGNOR:LIGGETT GROUP INC., A DE CORPORATION;REEL/FRAME:005733/0292
Effective date: 19910610
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK
Nov 13, 1990ASAssignment
Owner name: LIGGETT GROUP INC.
Free format text: CHANGE OF NAME;ASSIGNOR:LIGGETT & MYERS TOBACCO COMPANY;REEL/FRAME:005509/0149
Effective date: 19900726
Jul 5, 1990ASAssignment
Owner name: LIGGETT & MYERS TOBACCO COMPANY, A DE CORP., DELAW
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:LIGGETT GROUP INC., A CORP. OF DE;REEL/FRAME:005371/0796
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, NEW YORK
Free format text: SECURITY INTEREST;ASSIGNOR:LIGGETT & MYERS TOBACCO COMPANY, A CORP. OF DE;REEL/FRAME:005371/0782
Effective date: 19900629
Jul 5, 1990AS06Security interest
Owner name: LIGGETT & MYERS TOBACCO COMPANY, A CORP. OF DE
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK
Effective date: 19900629
Nov 8, 1989AS06Security interest
Owner name: LIGGETT GROUP INC., A DE CORP.
Effective date: 19891027
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK
Nov 8, 1989ASAssignment
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, NEW YORK
Free format text: SECURITY INTEREST;ASSIGNOR:LIGGETT GROUP INC., A DE CORP.;REEL/FRAME:005208/0941
Effective date: 19891027
Mar 30, 1987ASAssignment
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT
Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC., A CORP. OF DE.;REEL/FRAME:004688/0579
Effective date: 19870325
Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC.;REEL/FRAME:004688/0579