US3327715A - Tobacco smoke filter - Google Patents

Description

June 27, 1967 J. 1 AZORLOSA 3,327,715

TOBACCO SMOKE FILTER Filed Oct. 2, 1964 am o 96 P?) 4 3 Fig l.

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Julian L. Azorioso INVENTOR BY y / ATTORNEYS United States Patent 3,327,715 TOBACCO SMOKE FILTER Julian L. Azorlosa, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware Filed Oct. 2, 1964, Ser. No. 401,025 8 Claims. (Cl. 131-101) The present invention relates, in general, to minimizing certain undesirable effects obtained from the combustion of tobacco and, in particular, to improved tobacco products.

With the discovery that certain residues from tobacco smoking were physiologically objectionable to the human body and produced or were directly responsible for lung cancers, many attempts have been made to remove such residues during processing of the tobacco or to remove the same during the tobacco combustion process. The latter attempt has probably received the most attention since it is more economical and simpler to execute. The general public is probably more familiar with the end product of the latter treatment under the popular term filter cigarettes. The term filter cigarette is generally applied to those products which have at one end thereof a filtering material containing an adsorbent capable of adsorbing tars and irritants, through which the smoke is passed prior to inhalation by the smoker thereof. The filter, of course, should not substantially interfere with the pleasurable act of smoking from the standpoint of flavor and, physically, should not deter the passage of air through the filter while simultaneously removing tars and irritants from tobacco smoke.

Accordingly, it is an object of this invention to provide an improved filtering material for removing tars and irritants from tobacco smoke.

Another object of this invention resides in the provision of an improved filtering medium for filter cigarettes which is capable of adsorbing tars and irritants yet does not interfere with the passage of air through the filter or substantially detract from the flavor of the smoke to the user thereof.

Other objects, features and advantages of the invention will become further apparent hereinafter from the more detailed description of the invention which follows.

In accordance with the aforesaid objects of the invention methods and products have been devised comprising a tobacco product and as a filtering medium therefor 21 filter comprising essentially insoluble polymers of N- vinyl-alpha-pyrrolidones.

As used herein the terms insoluble polymers of N- vinyl-alpha-pyrrolidones and insoluble polyvinyl pyrrolidone are intended to include products which are insolu ble in water, strong mineral acids, caustic solutions and common organic solvents, and to distinguish such products from the soluble polymeric materials based on N- vinyl-alpha-pyrrolidone known in the art as represented by US. Patents Nos. 2,265,450, and 2,335,454. Such insoluble polymers of the type referred to above can be produced in accordance with the teachings of F. Grosser, as set forth in US. Patent 2,938,017, patented May 24, 1960.

The insoluble polymers of vinyl lactams are preferably employed in the form of a filter element for removing the tars and gums from tobacco smoke in cigarettes, pipes or cigars.

The single sheet of drawings illustrates various preferred embodiments of such filter elements. In the drawings FIGURES 1 and 2 illustrate filter-tip cigarettes; while FIGURE 3 illustrates a holder for cigarettes or cigar; and FIGURE 4 illustrates a pipe.

As illustrated in FIGURE 1, a cigarette designated as 1 may be provided with a cylindrical filter element comprising a cylindrical wall, 2, filled with granules of insoluble polyvinyl pyrrolidone 3; and held in place by cotton or other fibrous packing 4. Another form of cigarette is illustrated in FIGURE 2 wherein 11 designates a cigarette; while 12 designates the cylindrical wall of a filter element filled with a mixture of fibers 13 of cotton, cellulose acetate or other fibrous material and granules of insoluble polyvinyl pyrrolidone 14.

It is also possible to employ separate disposable filter elements particularly when using a cigarette or cigar holder. As shown in FIGURE 3 a cigarette or cigar 21 may be held in metal or plastic hollow holder 22, in the central opening of which there is placed a tube of paper, plastic, metal foil or the like 23 which is filled with granules 24 of insoluble polyvinyl pyrrolidone retained therein by plugs 25 of cotton or other suitable fibrous material.

Such disposable filters can also be employed in pipes by providing an enlarged chamber in the end of the pipe stem 31 as illustrated in FIGURE 4, in which there is placed a removable cylindrical element 32 of paper, metal foil, plastic or the like which is filled with granules 33 of insoluble polyvinyl pyrrolidone held in place therein by plugs 35 of suitable fibrous material.

While I particularly prefer the insoluble polymers N-vinyl-alpha-pyrrolidone, insoluble polymers of other N-vinyl lactams, can be used to obtain similar results.

Preferred N-vinyl lactams which find immediate and practical utility in the practice of the present invention are those characterized by the formula:

(OHRM CH=CH2 wherein R represents a member of the group consisting of hydrogen and alkyl groups containing from 1 to 4 carbon atoms and n represents a whole positive integer of from 2 through 4.

While the insoluble polymers of polyvinyl pyrrolidone and its hemologues which are illustrated by the above formula are particularly preferred, a number of other lactams can readily be vinylated in the manner described in US. Patent 2,317,084 and the insoluble polymers thereof may be employed in practicing the above invention. Broadly, the N-vinyllactams WhOSE insoluble polymers may be employed in practicing the present invention, may be illustrated by the following general formula:

wherein R and R represent hydrogen, alkyl or aryl and n and n represent an integer from 0 to 5 inclusive but only one of the n and n values may be 0. Y represents O *S 2 2-pyrrolidone, 4-acryl-2-pyrrolidone, -ethyl-2-pyrrolidone, 3-methyl-2-pyrrolidone, 4-methyl-2-pyr-rolidone, 5- methyl-Z-pyrrolidone, 3,3,5-trimethyl-2-pyrrolidone; 2- pi-peridone, 5,5-diethyl-2-piperidone, 5,6-di-methyl-2-pi-peridone, 4-ethyl-2-piperidone, 6-ethyl-2-piperid-one, 6-ethyl- B-methyI-Z-piperidone, 3-methyl-2-piperidone, 4-methyl-2- piperidone, S-methyl-Z-piperidone, 6-methyl-2-piperidone; 2-caprolactam, 3,6-dimethyl-2-caprolactam, 4,6-dimethyl- 2-caprolactam, 4,7-dimethyl-2-caprolactam, 7,7-diethyl-2- caprolactam, S-ethyl-Z-caprolactam, 5-ethyl-2caprolactam, 6-ethyl-2-caprolactam, 7-ethyl-2-caprolactam, 4- ethyl-6-methyl-2-caprolactam, 6-ethyl-4-methyl-2-caprolactam, 3-methyl-2-caprolactam, 4-methyl-2-caprolactam, 5-methyl-2-caprolactam, 6-methyl-2-caprolactam; 2-oxazinidinone (e.g. U.S.P. 2,905,669 and U.S.P. 3,097,087), 5-ethyl-2-oxazinidinone, 5-pl1enyl-2-oxazinidinone, 4,5dimethyl 2 -oxazinidinone, 5,5-dimethyl-Z-oxazinidinone, 2,S-diphenyl-Z-oxazinidinone, 2-phenyl-4-oxothiazolidone, 2,2-diphenyl-4oxathiazolidone, 2,2 dimethyl-4-oxothiazolidone; 2-oxazolidinone (deriv. in U.S.P. 2,905,690 and U.S.P. 2,891,058), 5-methyl-2-oxazolidinone, 4-methyl-2- oxazolidinone, 5-ethyl-2-oxazolidinone, 4,5-dimethyl-2- oxazolidinone, 2-phenyl-2-oxazolidinone, 5-butyl-2-oxazolidinone, 5-propyl-=2-oxazolidinone, 4,5-diethyl-2-oxazolidinone; 3-morpholinone disclosed in U.S.P. 2,987,509 e.g. 5-methyl-3-morpholinone, 5-ethyl-3-morpholinone) and the E-1353 products namely 3,5-dirnethyl-3anorpholinone) and the 2 alkyl and 6-alkyl derivatives; 2-piperazinone (e.g. JACS 62, 1202 (1940), the 3,3-dimethyl-2- ketopiperazine, 3-methyl-2-ketopiperazine; 4-thiazolidone (e.g. JACS, 76, 578 (1954), 2-methyl-4-thiazolidinone; 2-phenyl-4-thiazolidinone; 2-phenyl-4-thiazolidinone dioxide; Z-thiazolidone (J. Chem. Soc., 1949, 2367); 3-thiamorpholinone; 2-pyrimidone (e.g. .T. Chem.'Soc. 1959, 525); Z-imidazolidones (e.g. Ann., 232, 1222 (1885), N,N-ethylenethioureas (e.g. J. Biol. Chem, 163, 761 (1946); tetrahydro-ZH, 1,3)-oxazin-3-ones (e.g. U.S.P. 2,940,971), and the like.

The aforesaid insoluble polymers of the above-men tioned N-vinyl lactams can be readily prepared by heating the same at elevated temperatures in the presence of a catalyst such as alkali metals, alkaline earth metals as well as the oxides, hydroxides and alkoxides of these metals.

Another group of catalysts which have been found effective in producing insoluble polymers of N-vinyl lactarns include the hydrides and borohydrides of the alkali metals. Representative alkali metal hydrides and borohydrides which have been tested and found efiective include sodium borohydride, potassium borohydride and sodium hydride. Other alkali metal hydrides and borohydrides which can also be employed include lithium hydride, lithium borohydride, cesium hydride, cesium borohydride, rubidium hydride and rubidium borohydride. If desired, mixtures of alkali metal hydrides and/or alkali metal borohydrides can be employed as catalysts for the polymerization.

Similar results can be obtained by applying a small amount of insoluble polyvinyl pyrrolidone to tobacco, preferably in the tobacco portion used in the filter end of the cigarette or cigar, either in the leaf at any stage of its processing before or after it is ground or cut.

The following examples will serve to illustrate the practice of the invention.

Example 1 A one and one-half inch length of ten millimeter diameter glass tubing was loosely packed to a height of one-half inch with powdered cellulose acetate, a conventional cigarette filter material. Small adsorbent cotton plugs were used to retain the material in the tube. A Phillip Morris cigarette was then smoked as completely as possible through the filter. The filter material, i.e. cellulose acetate, was then removed and dissolved in a 1:4 combination of ethanol and ethylene dichloride. The res-ulting solution was then measured for light absorption at 400 millimicrons on a Hardy Spectrophotometer. The absorption readings are indicative of the test materials efiiciency for trapping tars and other irritants in the tobacco smoke. The free drawing properties of the filter for the life of the cigarette were also noted.

Example 2 The same procedure as set forth in Example 1 was em ployed except that a water soluble polyvinyl pyrrolidone, having a Fi'kentscher K value of 30, of -200 mesh, was employed to prepare the filter.

Example 3 The same procedure as set forth in Example 1 was employed except that a 50:50 mixture of the filter materials of Examples 1 and 2 was employed to prepare the filter.

Example 4 The same procedure as set forth in Example 1 was employed except that an insoluble polyvinyl pyrrolidone of 100-200 mesh produced as described in Example 1 of U.S. Patent 2,938,017 was employed to prepare the filter.

The data and results obtained are summarized in the following Table 1:

TABLE 1 Example Absorption at 400 m Remarks 1 0.83 Free drawing filter.

0.28 Filter clogged after few putts. 0. 8 o. 0.96 Free drawing filter.

Equal parts by weight of cellulose acetate fibers of 5 denier per filament and powdered insoluble polyvinyl pyrrolidone of 100-200 mesh and produced as described in Example 1, U.S. Patent 2,938,017, were intimately mixed by rolling in a one'half filled jar for several hours. They were then made up into cigarettes on a cigarette making machine and cut into plugs having a length of These filter plugs were attached to the end of regular cigarettes (non-filter) by an outer wrapping of pressure sensitive adhesive tape. Similar filter plugs were made up of the same cellulose acetate fibers unmixed with the insoluble polyvinylpyrrolidone. These plugs were also attached as filters to the same type cigarettes in the similar manner. Both cigarettes were smoked to within about A" of the filter and it was noted that the smoke from those cigarettes having a filter containing the insoluble polyvinylpyrrolidone was much milder than that from the cigarette having only a cellulose acetate filter.

Example 6 In a manner similar to that described in Example 5, equal parts by weight of cigarette tobacco and powdered 100-200 mesh) insoluble polyvinylpyrrolidone, produced in the manner described in Example 1 of U.S. Patent 2,938,017, were mixed and made-up into filter plugs which were attached to non-filter cigarettes by an outer wrapping of pressure sensitive adhesive tape. Similar plugs were also made-up of the same cigarette tobacco and attached to cigarettes from the same batch. Both types of cigarettes were smoked and it was noted that the smoke from the cigarettes in which the filter contained insoluble polyvinylpyrrolidone Was much milder than that from the other cigarettes.

'The amount of insoluble polyvinyl pyrrolidone employed to effect the desired decrease in irritational properties of the tobacco or the smoke therefrom should be a minimum amount because of the relatively high cost of insoluble polyvinyl pyrrolidone. Such amount may vary with various types of tobacco and With the method in which the insoluble polyvinyl pyrrolidone is incorporated in the tobacco. The optimum amount can, however, be determined by preliminary tests.

While the invention has been described with particularity regarding certain preferred embodiments thereof, it is obvious that various modifications and equivalents Will occur to those skilled in the art. Thus, it is intended, by the appended claims to cover such modifications and equivalents insofar as the state of the art permits.

What is claimed is:

1. A cigarette comprising a tobacco element and a filter element comprising an insoluble polymeric N-vinyl lactam.

2. A cigarette comprising a tobacco element and a filter element comprising an insoluble polymeric N-vinyl pyrrolidone.

3. A cigar comprising a tobacco element and a filter element comprising an insoluble polymeric N-vinyl lactam.

4. A cigar comprising a tobacco element and a filter element comprising an insoluble polymeric N-Vinyl pyrrolidone.

5. A smoke-filter for tobacco smoke comprising a holder for the article producing said smoke, said holder containing an insoluble polymeric N-vinyl lactam.

6. A smoke-filter for tobacco smoke comprising a holder for the article producing said smoke, said holder containing an insoluble polymeric N-vinyl pyrrolidone.

7. A filter element for use in smoking devices comprising an insoluble polymeric N-vinyl lactam.

8. A filter element for use in smoking devices comprising an insoluble polymeric N-vinyl pyrrolidone.

References Cited UNITED STATES PATENTS 2,770,241 11/ 1956 Winkler 1. 131208 2,792,006 5/1957 Marek 131-410 3,217,719 11/1965 Spears et al. 131208 SAMUEL KOREN, Primary Examiner. D. J. DONOHUE, Assistant Examiner.

Claims (1)

1. 7. A FILTER ELEMENT FOR USE IN SMOKING DEVICES COMPRISING AN INSOLUBLE POLYMERIC N-VINYL LACTAM.

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