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Publication numberUS3109436 A
Publication typeGrant
Publication dateNov 5, 1963
Filing dateNov 2, 1961
Priority dateNov 2, 1961
Publication numberUS 3109436 A, US 3109436A, US-A-3109436, US3109436 A, US3109436A
InventorsAbraham Bavley, Resnik Frank E
Original AssigneeAbraham Bavley, Resnik Frank E
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Tobacco products
US 3109436 A
Abstract  available in
Images(6)
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Claims  available in
Description  (OCR text may contain errors)

United States Patent 3,109,436 TOBACCO PRODUCTS Abraham Bavley, 9817 Oldfield Drive, Bon Air 35, Va.,

and Frank E. Resnik, 10024 Hobby Hill Road, Richmond, Va. No Drawing. Filed Nov. 2, 1961, Ser. No. 149,540 18 Claims. (Cl. 131-17) This invention relates to tobacco products and more particularly relates to tobacco compositions which will release a controlled amount of nicotine upon pyrolysis.

It has long been known in the tobacco industry that it is desirable to maintain the nicotine content of tobacco products at a uniform level, in order to provide a satisfying smoke. However, it is difficult to accomplish this result, since the nicotine content of tobacco varies widely, depending on the type of tobacco and the conditions under which the tobacco is grown.

Among the factors alfecting the nicotine content of any variety of tobacco are the conditions which exist during the growth of the tobacco, for example, the moisture conditions, the type of soil, the fertilizers that are employed, the number of tobacco plants per acre and the care which is given to the plants during their growth. The nicotine content also varies Widely, depending on the variety of tobacco. Many of the newer varieties of tobacco plants yield tobacco which is low in nicotine. Furthermore, methods of preparing tobacco products frequently remove some or all of the nicotine that is naturally present in the tobacco. In addition, modern technology has made it possible to utilize portions of the tobacco plant other than the leaves for smoking and some of these portions, such as the petioles, are low in nicotine content.

Maintaining the nicotine content at a suificiently high level to provide the desired physiological activity, taste, and odor which this material imparts to the smoke, without raising the nicotine content to an undesirably high level, can thus be seen to be a significant problem in the tobacco art.

The addition of nicotine to tobacco in such a way that it remains inert and stable in the tobacco product and yet is released in a controlled amount into the smoke aerosol when the tobacco is pyrolyzed is a result which is greatly desired.

Previous efforts to adjust the amount of nicotine in tobacco have not been successful. It has not been feasible to add nicotine per se to tobacco products. Since it can be absorbed through intact skin, nicotine is diflicult and hazardous to handle in processing operations. In addition, free nicotine is unstable material and has been found to decompose readily at room conditions. Thus, if nicotine were simply added as the free material to tobacco, it would be likely to decompose during storage of the tobacco product, thereby resulting in the formation of undesirable decomposition products and resulting in a decrease in nicotine. Even though the nicotine content of tobacco products could, by the addition of nicotine under conditions involving considerable effort, be made initially uniform, the decomposition attending storage of the product would not provide a smoke containing a uniform amount of nicotine.

The present invention provides a solution to this longstanding problem and results in accurate control of the amount of nicotine which is released in tobacco smoke. By employing the methods and compositions of the pres- 3,199,436 Patented Nov. 5, 1963 Ice ent invention, it is possible to eliminate the hazards of handling nicotine and to incorporate exact amounts of nicotine in a tobacco composition which will remain constant over extended periods of time and which will ultimately yield a smoke containing a controlled amount of nicotine.

The present invention comprises incorporating into a tobacco product a material which can be characterized as a nicotine-cation ion exchange resin (referred to hereinafter for convenience as a nicotine-cation exchange resin). The resulting composition is inert and stable and can be employed in a cigarette filler, in pipe tobaccos, in cigars or in other tobacco products. The nicotine-cation exchange resin will not decompose under ordinary storage conditions and does not impart undesirable odors to the tobacco. However, when the tobacco is smoked, nicotine is released from the nicotine-cation exchange resin and goes into the smoke. The amount of nicotine which is desired in the smoke can be adjusted within desired limits by the proper control of the amount of nicotine-cation exchange resin which is initially incorporated in the tobacco.

The nicotine-cation exchange resin, which will hereinafter also be referred to as the nicotine-resin, can be prepared by contacting a cation exchange resin with nicotine under either continuous or batch conditions. When the contacting is done in the batch state, the reactants are agitated in a reaction flask with a volume of resin, which can, for example, comprise from 20 to 30% by weight of the reactant. The amount of materials the temperature and the time of operation will depend upon the reactants involved. The mixture is agitated by shaking or stirring. The use of a fine mesh resin will minimize any physical deterioration of the resin which might be caused by a stirrer. Particles in the range of -200 mesh are preferred. At the end of the reaction period, the solution can be decanted and the suspended resin recovered by filtration. The resin can then be rinsed and air-dried and it is then ready for use. The solvent is preferably water, although the other inert liquids in which the nicotine is soluble can also be employed.

Continuous operation in a column can be effected by placing pretreated resin in a column of suitable size and passing the reactants through the column continuously.

Preferably, the contacting is conducted under continuous conditions. This can be done by packing a column with the ion exchange resin in particulate form, for example bead form, and passing an aqueous solution of nicotine through the column. The technique employed can be the same as is used in chromatographic columns. As in the the case of the batch contacting, other inert liquids may be employed in place of water.

In either the batch or continuous method, after the desired amount of nicotine has been taken up by the resin, the resin can be removed from the contacting vessel directly employed in accordance with the present invention.

The exact amount of nicotine which is incorporated in the resin can be determined by methods Well known in the art. For example the method set forth by R. B. Grifiith in Tobacco Science, volume 1 (1957), on pages -137 may be employed. Another method is that described in the Official and Tentative Methods of Analysis of the Association of Official Agricultural Chemists, Fourth Edition, 1935.

The proportion of nicotine in the resin is not critical,

* I a lit-11+ lLNJ 71+ [ND Resin Nicotine Nicotine-resin The above equation represents the reaction when the cation exchange resin is in the hydrogen ion form, as will be described below. A similar reaction could occur with a cation exchange reaction in which the hydrogen ion were replaced with another ion such as sodium ion, potassium ion or other ions. However, the hydrogen ion type is preferred, because it is more easily replaced by nicotine and more readily takes up the nicotine upon contact.

Cation exchange resins which may be employed in accordance with the present invention may be strong cation type resins, intermediate cation type resins or weak cation type resins and can, for example, be any of the commercially available cation exchange resins.

Satisfactory strong cation exchange resins include the sulfonic acid types, such as resins formed by cross-linking polystyrene with divinylbenzene and sulfonating the crosslinked product. Such resins are illustrated by the structural formula:

There are numerous commercial cation exchange resins of this type, including Amberlite IR 112H+, Amberlite IR 120-H (both are manufactured by Rohm and Haas Co.), Dowex 50 W-X8 (manufactured by the Dow Chemical Co.) and the like.

Satisfactory intermediate cation exchange resins include phosphonic acid types, such as resins formed by crosslinking polystyrene with divinylbenzene and reacting the cross-linked product with phosphonic acid to incorporate a phosphonic acid difunctional group on the styrenedivinylbenzene lattice. Such resins are illustrated by the structural formula:

i oan, ioam Illustrative of a commercially available resin of this type is Bio-Rex 63 (manufactured by Bio-Rad Laboratories).

Satisfactory weak cation exchange resins include carboxylic acid types, such as resins formed by copolymerizing methacrylic acid with a cross-linking agent, for

example divinylbenzene. Such resins are illustrated by the structural formula:

Illustrative of a commercially available resin of this type is Amberlite CG SO-type l (manufactured by Rohm and Haas Co.) which is described as a synthetic weakly acidic cation exchange resin; carboxylic acid type; hydrogen form.

Another type of Weak cation exchange resin comprehends resins having an -OH group as the ion functional group and formed by reacting polyhydric phenols with formaldehyde. Such resins are illustrated by the structural formula:

Such resins may be further modified by the addition of one or more additional functional groups. For example, the above phenol-formaldehyde resin may be sulfonated to introduce sulfonic groups, giving a resin having both SO3H and OH groups, as illustrated in the structural formula:

SOsl-I SOaH Other variations of cationic exchange resins may also be employed. For example, suitable resins include carbonaceous cation exchange resins of the sulfonated coaltype, in either the hydrogen or sodium condition, i.e. in which the ion, which is replaced by the nicotine is either hydrogen or sodium. Such resins are commercially obtainable as, for example Zeo-Karb resins. Another type of resin which is suitable is the Zeolite type, either natural or synthetic. These resins are hydrated alkalialuminum silicates.

The nicotine-resin can be applied to tobacco in many different ways. For example, it can be used directly as it is taken from the reaction vessel after its preparation, or it can first be ground to form smaller particles. The resin particle size can vary widely. The nicotineresin particles can be admixed with a sticker, such as a corn syrup solution, honey, molasses or other similar material, and can then be sprayed on, admixed with or otherwise applied to the tobacco.

The nicotine-resin can be employed with tobacco prod nets of all kinds, including cigarette filler, cigar filler, pipe tobacco and the like.

The amount of nicotine-resin that is added to the tobacco will vary depending upon the nicotine content originally present in the tobacco and upon the nicotine content desired in the tobacco. Generally, the nicotine content of the tobacco is brought to a level whereby there are 0.13.0 mg. of nicotine in the smoke per cigarette.

One method of determining how much of a particular nicotine resin to add to a particular tobacco is to analyze the smoke for nicotine, which can be done by conventional methods, such as is described in the Journal of the Association of Ofiicial Agricultural Chemists (vol. 42) (Nov. 2, 1959) on pages 424-429. In accordance with this method an aqueous solution of smoke particulate phase is steam distilled under appropriate conditions; this is followed by spectrophotometric examination of the resulting distillate in the ultraviolet spectral region.

The directions for the details ofthis procedure include the following:

Collect the smoke particulate phase from successive cigarettes, using a standard robot smoking procedure ml. puii volume taken over a 2 second interval, once per minute) upon a glass wool plug or an equivalent collection medium suitable for the separation of 0.1a particles and larger from a gas particulate phase mixture. Strip the nicotine alkaloids from the collection medium with four 10 ml. portions of 0.05 N HCl. Combine the separate eluates and dilute to exactly ml. with 0.05 N HCl. Transfer a 10 ml. aliquot of this solution to the port of the distillation unit. Distill approximately 100 ml., and discard. Make the sample in the unit alkaline by adding a size 00 capsule of NaCl and a size 00 capsule of NaOH, in that order. Repeat the distillation and collect a second 100 ml. portion, as follows: distill approximately 98 ml. into a 100 ml. volumetric 6 flask to which 5 ml. 3 N H 80 has previously been added. Dilute the distillate exactly to mark with distilled water, mix well, and examine spectrophotometrically between 230 and 300 m Correct the absorbance of the unknown solution at approximately 260 m by a baseline selected on the basis of the curve. Draw a line from the lowest point on both sides of the maximum absorbance. The difference between the baseline and peak at the wavelength of the peak is taken as the absorbance of the sample. Compare this corrected absorbance to the absorbance of the standard nicotine solution corrected in the same manner, and calculate the nicotine content of the sample directly from this comparison,

' using standard spectrophotometric technique.

Mg. nicotine alkaloid= (A/A) X (mg. known per ml. dilution factor/ no. cigarettes in sample); where A is corrected absorbance of unkown, and A is corrected absorbance of known. The nicotine-resin content for the tobacco can then be adjusted to bring the nicotine in the smoke to within the range which is desired.

The following examples are illustrative:

Example I Twenty-five grams of synthetic weakly acidic cation exchange resin of the carboxylic acid type, hydrogen form, having the trade name Amberlite CG50, type 1 (Rohm and Haas Co.) was placed in a 250 ml. beaker. Twenty milliliters of nicotine and ml. of distilled water were added to the beaker containing the resin. The resulting slurry was added to a 1-inch diameter chromatographic column, which was 36 inches long, and the slurry was eluted. Since it contained a large quantity of nicotine, the first 50 ml. of eluate was collected in a beaker and added to the column. The column was washed until the eluate was free of nicotine. This was determined by a spot test (a Konig reaction as described in I. Prakt. Chem. N.F. 69, pages 1-39 and -137 (1904). The nicotineresin, when removed from the column and dried, was ready for use as an additive to tobacco.

Example I] Nicotine was incorporated into a weak cation exchange resin of the type, and in the manner, described in Example 1.

Regular cigarette filler was divided into two portions. One portion was then set aside as a control and a second portion was employed to prepare experimental cigarettes, with the nicotine content increased by the addition of the nicotine-resin. The nicotine-resin was slurried in a Waring Blender with an aqueous solution of corn syrup to give it the proper consistency for spraying and was then sprayed on the second portion of filler. The control portion was sprayed with an aqueous solution of corn syrup alone. A standard nicotine analysis showed that the nicotine content of the experimental cigarette was approximately double that of the control. In the case of the control, the nicotine content was about 14 milligrams per cigarette, whereas in the cigarette containing the nicotineresin compound, the nicotine content was about 27 milligrams per cigarette.

The experimental cigarettes were smoked on a standard constant volume smoking machine. The pufis were of two-second duration and had a volume of 35 ml. The

cigarettes were smoked to a 25 mm. length and the smoke was collected on a Cambridge-type filter pad which trapped paritcles greater than 0.1 micron in size. All of the nicotine was trapped on this pad. The pads were removed. The nicotine alkaloids were stripped from the pads with four 10 ml. portions of 0.05 N HCl. The separate eluates were combined and diluted to exactly 50 ml. with 0.05 and HCl. A 10 ml. aliquot of this solution was transferred to a distillation unit. Approximately 100 ml. were distilled and discarded. The sample remaining in the distillation unit was made alkaline by adding a size 00 capsule of NaCl and a size 00 capsule of NaOH, in

that order. The distillation was repeated and a second 100 ml. pontion was collected as follows:

Approximately 98 ml. was diluted into a 100 ml. volumetric fiaskto which ml. 3 N H 80 has previously o to tine present in the tobacco filler prior to the addition of the resin was 14 mg./cigt., or 1.27%.

Cigarettes were also prepared using nicotine incorporated in Bio-Rex 63 resin (manufactured by Bio-Rad been added. The distillate was diluted exactly to mark 5 Laboratories), a phosphonic acid cation exchange resin with distilled water, mixed and was examined in' a Cary containing a phosphonic 'acid d ifunotional group on a spectrophotometer for its nicotine content. Analysis of styrene-divinylbenzene lattice. This material was used the smoke from these cigarettes showed that the nicotine in the acid form and had a particle size of 20-50 mesh. content of the smoke from the experimental cigarettes was This resin was used in Examples VT and VII. The figures increased 0.4 mg./cigt., or approximately 33% over that for these examples were obtained in a similar manner of the control. The smoke data obtained are given below: as in the case of Examples I-V.

In the table, after certain examples, the figures are I given for a control in which the identical filler was employed, without the addition of nicotine-resin. cigt.) The details and results of Examples 'III, IV, V, VI and VII are presented in the following table. Ranges of addition of resin to tobacco filler and the resulting int? crease in the nicotine content of the smoke due to the incorporation of the nicotine-resin can be seen from the table. It can be seen from the table that the nicotine Average 1. 6 content of the smoke has been increased in a range of from 0.1 to 0.8 mg. er cigarette over the controls.

Nicotine in Nicotine eigt. filler Theoretical Actual amt. Total nico- Nicotinein Total amt. increase in Cigt. typo prior to the amt. of resin of resin tine content filler from of nicotine the smoke addition of added, added, of cigt. filler, resin, in smoke, due to the resin, mg./cigt; mg./clgt. mglcigt. mg./cigt. mglcigt. resin, mglcigt. mg./cigt.

Example III l4. 0 5O 47. 6 27. 0 13. 0 1. 6 0. 4 Control 14. O 0 0 14. O 0 1. 2 0

1 NOTE-same control for Examples IV and V.

Examples 111, IV, V, VI and VII We claim: V Cigarettes were prepared using nicotine incorporated mliaccqwmwsmon coniprlimg tobacco and a n1cot1ne-cat1on 1on exchange resin an an amount sufinto Dowex SOW-XS resin, a strong cation exchange resin f rcient to release mcoune upon pyrolysls or said tobacco. of the sulfomc acid type. This resin was used 1n Ex- 12 A t b t b d m 1e IV They Were prepared to give a theoretical yield O Composl Ion P o acco a a P r L nicotine-cation 1on exchange resin 1n an amount sufiiclent of 10 mg. of resin per cigarete (22.8% of the treated to release nicotine upon pyrolysis of said-tobacco of the resin was nlcotme). The theoretical amount of nlcotine sulphonic acid type l liifilt iitiEli!it?!aofififlliitfitliiid tfii A a m ones Ondin to 10 5 m of the resin The nicotine-cation ion exchange resin in an amount sufiicient 1g p g y to release nicotine upon pyrolysis of said tobacco of the amount of mcotme present in the tobacco filler pr1or to phosphonic acid type f g of the ri was 1% p 4. A tobacco composition comprising tobacco and a h i g li g ig E zl g nicotine-cation ion exchange resin in an amount sufiicient m 0 m er a S q Ion exc to release nicotine'upon pyrolysis of said tobacco of the resln of the sulfonic acid type. Thls resin was used 1n carboxylioacid type i Y g g g Win-e prepilreii to i g 5. A tobacco composition comprising tobacco and a mum Y O 0 resm Per Plgaette (3J3 of nicotine-cation'ion exchange resin in an amount sufficient h resm was n1ct1ne)- The theoretical amount of 1 to release nicotine upon pyrolysis of said tobacco of the tine would have been 7.1 mg./c1gt. Chemical analysis of h nol f r ld h d type. the tobacco filler showed that the actual nicotine content 6 A tobacco composition comprising (tobacco and a W 1118/ cofrespondlng 0f the nicotine-cation ion exchange resin in an amount suf- The of nlcotlne Present 111 the tobafico finer P ficient to release nicotine upon pyrolysis of said tobacco to the add1t1on of the resln was 18.5 mg./c1gt., or 1.67%. 5 of h lfon t d coal typg clgafettes also P p 115mg nicotine iIICOTPO- 7. A process for incorporating a controlled amount of rated 1n emberhte CG-SQ, type 1 (IR-50) a weakly nicotine in tobacco comprising incorporating in the toacidic cation exchange resin of the carboxyhc type, hybacco a nicotine-cation ion exchange resin in an amount drogen form. Thls resin was used in Example III. Cigasuflicient to release nicotine upon pyrolysis of said torettes were prepared to g1ve a theoretlcal yield of 50 mg. bacco. of Tesln P clgal'ette 111% resin as t 8. A process for incorporating a controlled amount of The theoretical amount of nicotme would have been 13.6 nicotine in tobacco comprising incorporating in the tomg/Clgtchenilcal'amflyses 0f the tobacco fi fir h w d bacco a nicotine-cation ion exchange resin in an amount that the actual nlcotine content was 13.0 mg./cigt. corresuificient to release nicotine upon pyrolysis of said tosponding to 47.6 mg. of the resin. The amount of nice bacco, of the sulfonic acid type.

9. A process for incorporating a controlled amount of nicotine in tobacco comprising incorporating in the tobacco a nicotine-cation ion exchange resin in an amount suflicient to release nicotine upon pyrolysis of said tobacco, of the phosphonic acid type.

10. A process for incorporating a controlled amount of nicotine in tobacco comprising incorporating in the tobacco a nicotine-cation ion exchange resin in an amount sufiicient to release nicotine upon pyrolysis of said tobacco, of the carboxylic acid type.

11. A process for incorporating a controlled amount of nicotine in tobacco comprising incorporating in the tobacco a nicotine-cation ion exchange resin in an amount sufficient to release nicotine upon pyrolysis of said tobacco, of the phenol-formaldehyde type.

12. A process for incorporating a controlled amount of nicotine in tobacco comprising incorporating in the tobacco a nicotine-cation ion exchange resin in an amount sufiicient to release nicotine upon pyrolysis of said tobacco; of the sulfonated coal-type.

13. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount sufficient to release nicotine upon pyrolysis of said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking.

14. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount sufficient to release nicotine upon pyrolysis of said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking, said cation ion exchange resin being of the sulfonic acid type.

15. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount sufiicient to release nicotine upon pyrolysis of 10 said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking, said cation ion exchange resin being of the phosphonic acid type.

16. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount sufiicient to release nicotine upon pyrolysis of said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking, said cation ion exchange resin being of the carboxylic acid type.

17. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount suificient to release nicotine upon pyrolysis of said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking, said cation ion exchange resin being of the sulfonated coaltype.

18. A tobacco composition comprising smoking tobacco and a nicotine-cation ion exchange resin in an amount sufficient to release nicotine upon pyrolysis of said tobacco which, upon smoking of the tobacco, releases nicotine into the smoke resulting from the smoking, said cation ion exchange resin being of the phenol-formaldehyde type.

References Cited in the file of this patent UNITED STATES PATENTS 2,739,598 Eirich Mar. 27, 1956 2,815,760 Schreus et al. Dec. 10, 1957 FOREIGN PATENTS 501,402 Belgium Mar. 15, 1951 497,708 Great Britain Dec. 19, 1938 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3.109.436 November 5 1963 Abraham Bavley et al.

It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

In the grant lines I and 2, for "Abraham Bavley of Bon Air Virginia, and Frank E. Resnik of Richmond Virginia read Abraham Bavley of Bon Air Virginia. and Frank E. Resnik, of Richmond, Virginia, assignors to Philip Morris Incorporated, of New York, N. Y. Y a corporation of Virginia, line 11, for "Abraham Bavley and Frank E. Resnik their heirs" read Philip Morris Incorporated its successors in the heading to the printed specification lines 3 to 5 for "Abraham Bavley 9817 Oldfield Drive. Bon Air 35 Va. and Frank E. Resnik, 10024 Hobby Hill Road Richmond Va." read Abraham Bavley Bon Air, Va. and Frank E. Resnik, Richmond Va. assignors to Philip Morris Incorporated New York N. Y. q a corporation of Virginia column 3, lines 11 to 18. the left-hand portion of the formula should appear as shown below instead of as in the patent:

Signed and sealed this 12th day of May 1964.

(SEAL) Attest:

ERNEST W. SWIDER EDWARD J. BRENNER Attesting Officer Commissioner of Patents

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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3280823 *Oct 1, 1963Oct 25, 1966Philip Morris IncAdditive-releasing filter for releasing additives into tobacco smoke
US3422819 *Mar 30, 1966Jan 21, 1969Imp Tobacco Co LtdCigarettes and paper therefor
US3847326 *Mar 18, 1971Nov 12, 1974Ici LtdTobacco composition
US3901248 *Aug 15, 1974Aug 26, 1975Leo AbChewable smoking substitute composition
US3924642 *Nov 15, 1972Dec 9, 1975Haarmann & Reimer GmbhTobacco and tobacco substitute material including metal chelate compounds
US4676259 *Mar 21, 1985Jun 30, 1987Advanced Tobacco Products Inc.Nicotine enhanced smoking device
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US4836224 *Dec 24, 1987Jun 6, 1989R. J. Reynolds Tobacco CompanyCigarette
US4917120 *Feb 7, 1989Apr 17, 1990Advanced Tobacco Products, Inc.Nicotine impact modification
US4920990 *Nov 23, 1988May 1, 1990R. J. Reynolds Tobacco CompanyCigarette
US20070137097 *Dec 16, 2005Jun 21, 2007Michio IkuraProduction of biodiesel from triglycerides via a thermal route
US20070144060 *Dec 14, 2006Jun 28, 2007Michio IkuraProduction of biodiesel from triglycerides via a thermal route
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Classifications
U.S. Classification131/352
International ClassificationA24B15/42, A24B15/00, A24B15/38
Cooperative ClassificationA24B15/38, A24B15/42
European ClassificationA24B15/42, A24B15/38