Ground tobacco composition

Information

  • Patent Grant
  • 11766067
  • Patent Number
    11,766,067
  • Date Filed
    Wednesday, May 9, 2018
    6 years ago
  • Date Issued
    Tuesday, September 26, 2023
    8 months ago
Abstract
Embodiments described herein include a ground tobacco composition, wherein at least 90% by weight of the tobacco in the composition has a particle size in the range of about 200 μm to about 5 mm.
Description
PRIORITY CLAIM

The present application is a National Phase entry of PCT Application No. PCT/EP2018/062116, filed May 9, 2018, which claims priority from GB Patent Application No. 1707758.7, filed May 15, 2017, which is hereby fully incorporated herein by reference.


TECHNICAL FIELD

The present invention relates to a ground tobacco composition which is particularly useful in the preparation of a tobacco extract, and methods of making the ground tobacco composition. The invention also provides a tobacco extract formed from the ground tobacco composition, cartridges containing the tobacco extract for use in a smoking article, and smoking articles comprising the tobacco extract.


BACKGROUND

Tobacco material is heated in smoking articles for the purpose of releasing substances contained in the material and delivering these as an aerosol.


Smoking articles such as cigarettes, cigars and the like burn tobacco during use to create tobacco smoke. Attempts have been made to provide alternatives to these articles that burn tobacco by creating products that release compounds without burning. Examples of such products are heating devices which release compounds by heating, but not burning, material. The material may be, for example, tobacco or other non-tobacco products, which may or may not contain nicotine.


Electronic cigarettes or “e-cigarettes” are another product that has been formulated as an alternative to combustible products. These devices contain a volatilizable solution which generates an inhalable aerosol on heating. These solutions may contain components of tobacco. It is therefore useful to be able to selectively extract tobacco components.


SUMMARY

According to a first aspect of the present invention, there is provided a ground tobacco composition, wherein at least 90% by weight of the tobacco in the composition has a particle size in the range of about 200 μm to about 5 mm.


When extracting components from tobacco, the particle size of the tobacco determines the distance that the tobacco components must diffuse within the tobacco leaf matrix in order to be extracted. Reduction of diffusional resistance by breaking tobacco leaf into small particles increases the rate of leaching of tobacco constituents out of the tobacco. Furthermore, this increases the tobacco surface area thereby increasing contact between the tobacco and extraction solvent.


The inventors have also found that through using a finely ground tobacco, the distribution of tobacco components through the ground tobacco is more consistent and any resulting extract composition has improved consistency, as compared to tobacco extracts obtained from ground tobacco with a larger particle sizes.


On the other hand, extraction solvents flow through a bed of ground tobacco during the extraction process. The separation between particles is greater for larger particles, allowing improved solvent flow and consequently more efficient extraction. Moreover, a narrow particle size distribution improves solvent flow; a wider range of particle sizes can result in a tobacco bed in which small tobacco particles fill spaces between larger particles thereby blocking solvent flow.


Further, very fine particles are more likely to be carried in a solvent flow during extraction, contaminating the tobacco extract and/or soiling the extraction equipment.


Balancing these various considerations, the inventors have optimized the particle size and particle size distribution for ground tobacco which is to be subjected to one or more extraction processes.


In some cases, at least 90% by weight of the tobacco in the composition has a particle size in the range of about 355 μm to about 3.5 mm.


The inventors have found that the concentration of benzo[a]pyrene and the concentration of metals is higher in tobacco particles having a size of less than 355 μm than in particles having a size of 355 μm or more. As a result of removing tobacco particles having a size of less than 355 μm, the extract obtained by extraction from this ground tobacco composition, depending on the extraction solvent, typically contains less metal and/or benzo[a]pyrene than tobacco extracts obtained from previously known ground tobacco compositions.


In some cases, at least 95% by weight of the tobacco in the composition has a particle size in the specified range, suitably at least 97% by weight.


According to a second aspect of the invention, there is provided a method of preparing a ground tobacco composition as described herein, the method comprising;


(a) grinding tobacco; (b) removing tobacco particles that are larger than the particle size range using a first sieve; and (c) removing tobacco particles that are smaller than the particle size range using a second sieve.


According to a third aspect of the invention, there is provided a tobacco extract obtainable by extracting tobacco components from the ground tobacco composition described herein.


A fourth aspect of the invention provides a method of preparing a tobacco extract, the method comprising contacting a solvent with the ground tobacco composition described herein. In some cases, the method of preparing a tobacco extract comprises (a) grinding tobacco; (b) removing tobacco particles that are larger than the particle size range using a first sieve; (c) removing tobacco particles that are smaller than the particle size range using a second sieve; and (d) contacting the ground tobacco with an extraction solvent.


A fifth aspect of the invention provide a cartridge configured for use in a smoking article, the cartridge containing a tobacco extract according to the third aspect of the invention. A further aspect of the invention provides a smoking article containing a tobacco extract according to the third aspect of the invention or a cartridge according to the fifth aspect of the invention.


Further features and advantages of the invention will become apparent from the following description of preferred embodiments of the invention, given by way of example only.







DETAILED DESCRIPTION

The invention provides a ground tobacco composition, wherein at least 90% by weight of the tobacco in the composition has a particle size in the range of about 200 μm 5 to about 5 mm. In some cases, at least 90% by weight of the tobacco in the composition as a particle size that exceeds about 250 μm, 300 μm, 330 μm or 355 μm. In some cases, at least 90% by weight of the tobacco in the composition has a particle size that is less than about 4.5 mm, 4 mm or 3.5 mm. For instance, in some cases at least 90% by weight of the tobacco in the composition has a particle size in the range of about 300 μm to about 4 mm, suitably from about 355 μm to about 3.5 mm.


As used herein, reference to a lower particle size limit means that the tobacco particles will not pass through a sieve with a mesh size of that lower limit. For instance, restriction of the particle size to be greater than 200 μm means that the particles are retained on a sieve with a 200 μm mesh. Similarly, restriction of the particle size to be greater than 355 μm means that the particles are retained on a sieve with a 355 μm mesh.


As used herein, reference to an upper particle size limit means that the tobacco particles will pass through a sieve with a mesh size of that upper limit. For instance, restriction of the particle size to be less than 5 mm means that the particles are not retained on a sieve with a 5 mm mesh (i.e. they pass through a 5 mm mesh sieve). Similarly, restriction of the particle size to be less than 3.5 mm means that the particles are not retained on a sieve with a 3.5 mm mesh (i.e. they pass through a 3.5 mm mesh sieve).


In some cases at least 95% by weight of the tobacco in the composition has a particle size in the specified range, and suitably at least 97%, 98%, 99% or 99.5% by weight of the tobacco in the composition has a particle size in the specified range. In some cases, substantially all of the tobacco in the composition has a particle size in the specified range. In some cases, 100% by weight of the tobacco in the composition has a particle size in the specified range.


The ground tobacco composition is particularly suitable for use in the preparation of a tobacco extract. Any suitable extraction solvent may be used. In some cases, the extraction solvent may be an aerosol generating agent, so that the tobacco components are dissolved and retained in the aerosol generating agent. A tobacco extract formed using an aerosol generating agent as a solvent can be incorporated directly into an electronic cigarette or the like (or a cartridge configured for use with an electronic cigarette). In other cases, the extraction solvent may be, for example, a supercritical fluid, such as supercritical carbon dioxide. Where the extraction solvent is not an aerosol generating agent, the method of preparing a tobacco extract according to the invention may include a solvent switch in which the dissolved tobacco components are transferred from the extraction solvent to an aerosol generating agent. As used herein, an “aerosol generating agent” is an agent that promotes the generation of an aerosol on heating. An aerosol generating agent may promote the generation of an aerosol by promoting an initial vaporization and/or the condensation of a gas to an inhalable solid and/or liquid aerosol.


In general, suitable aerosol generating agents include, but are not limited to: a polyol such as sorbitol, glycerol, and glycols like propylene glycol or triethylene glycol; a non-polyol such as monohydric alcohols, high boiling point hydrocarbons, acids such as lactic acid, glycerol derivatives, esters such as diacetin, triacetin, triethylene glycol diacetate, triethyl citrate or myristates including ethyl myristate and isopropyl myristate and aliphatic carboxylic acid esters such as methyl stearate, dimethyl dodecanedioate and dimethyl tetradecanedioate. In some cases, the aerosol generating agent comprises one or more of glycerol, propylene glycol, triacetin and isopropyl myristate, suitably glycerol and/or propylene glycol.


EXAMPLE

The tobacco moisture content should be in the range of 0-30% by weight, ideally 12-16% by weight. Tobacco was fed into a ball mill type grinder, Urschel Comitrol 3600 with a 3 mm round cutting head.


The particles were then sieved to select particles of the desired size. The ground tobacco was then separated using two sieves; a first, upper sieve with a 3.5 mm mesh size and a second, lower sieve with a 0.355 mm mesh size.

    • Tobacco particles retained on the top sieve can be retained and returned to the grinder later.
    • Tobacco particles retained on the lower sieve were retained as the sample for extraction.
    • Tobacco particles passing through both sieves were discarded. The equipment used for sieving is a Russell Finex 17300 sieve.


Comparison of the starting tobacco material (pre-grinding) with the tobacco particles of sample for extraction shows there is no loss of nicotine or water during the processing steps. Further, the metal content of the starting tobacco material and the tobacco particles of Sample A is the comparable; there is not metal leaching from the processing apparatus into the tobacco.


Moreover, samples taken from different parts of a tobacco leaf were determined to have significant variations in the relative concentrations of various tobacco components. The ground tobacco of the sample for extraction was found to have reduced variation in the concentration of these components as compared to the tobacco leaf.


Chemical and Physical Analysis


Various tests were completed using Virginia tobacco and, separately, Burley Tobacco. The tests were completed following grinding and the various size bands were selected using appropriate sieves. The data are shown below.


a) Chemical Composition.


It can be seen from Tables 1 and 2 below that the concentration of benzo[a]pyrene and toxic heavy metals is highest in tobacco extracts obtained using tobacco particles that are smaller than 355 μm.











TABLE 1







Benzo[a]pyrene


Leaf Type
Particle size
in extract (ng/g)

















Virginia
200-355 μm
116



355-710 μm
100



 710-1400 μm
89.8



>1400 μm
90.8



All sizes
93.4


Burley
200-355 μm
5.26



355-710 μm
4.06



 710-1400 μm
3.79



>1400 μm
3.79



All sizes
4.02


















TABLE 2









Concentration in extract (ng/g)















Leaf Type
Particle size
Cd
Pb
Cr
Ni
As
Se
Hg



















Virginia
200-355
μm
962
870
1932
951
350
52.4
22.3



355-710
μm
786
238
402
369
70.4
41.7
18.6



710-1400
μm
788
262
329
345
58.7
42.1
17.8



>1400
μm
723
255
441
402
60
38
15.3
















All sizes
747
244
411
373
80.4
42.6
16.1
















Burley
200-355
μm
196
673
4001
1993
158
23.2
16.2



355-710
μm
220
156
646
868
38.4
32.4
16.9



710-1400
μm
198
159
542
799
37.8
29.2
14.8



>1400
μm
219
206
602
897
37.0
32.3
14.1
















All sizes
206
269
1104
1018
73
32.5
15.4










It can be seen from Table 3 below that the nicotine and moisture content was approximately equal for tobacco extracts obtained from all particle sizes.














TABLE 3







Leaf Type
Particle size
Nicotine (mg/mL)
Water (wt %)









Virginia
200-355 μm
27.6
12.1




355-800 μm
31.0
13.2




 800-2000 μm
31.6
13.6




>2000 μm
32.9
14.0




All sizes
33.3
13.7



Burley
125-355 μm
26.8
10.0




355-710 μm
31.4
12.2




 710-1400 μm
31.7
12.7




>1400 μm
30.2
12.9




All sizes
31.9
12.3










Tobacco extracts were formed by contacting tobacco particles with a 50:50 (w/w) mixture of glycerol and propylene glycol at 100° C. for 15 minutes. (The weight ratio of tobacco to solvent was 1:9). The nicotine concentration in the extracts was approximately the same for all particle size ranges used. The tobacco particle size does not affect the extract nicotine concentration.


b) Size Distribution


The particle size distribution following grinding was measured. The various size bands were selected using appropriate sieves.














Leaf Type
Particle size
Wt %

















Virginia
<200 μm
1.3



200-355 μm
1.4



355-710 μm
10



 710-1400 μm
29.5



>1400 μm
57.8



All sizes
100


Burley
<200 μm
1.4



200-355 μm
1.8



355-710 μm
17.4



 710-1400 μm
42.3



>1400 μm
37.1



All sizes
100









It can be seen that 2.7wt % of the Virginia tobacco and 3.2wt % of the Burley tobacco had a particle size of less than 355 μm.


The various embodiments described herein are presented only to assist in understanding and teaching the claimed features. These embodiments are provided as a representative sample of embodiments only, and are not exhaustive and/or exclusive. It is to be understood that advantages, embodiments, examples, functions, features, structures, and/or other aspects described herein are not to be considered limitations on the scope of the invention as defined by the claims or limitations on equivalents to the claims, and that other embodiments may be utilized and modifications may be made without departing from the scope of the claimed invention. Various embodiments of the invention may suitably comprise, consist of, or consist essentially of, appropriate combinations of the disclosed elements, components, features, parts, steps, means, etc., other than those specifically described herein. In addition, this disclosure may include other inventions not presently claimed, but which may be claimed in future.

Claims
  • 1. A method of preparing a tobacco extract from a ground tobacco composition, wherein at least 90% by weight of the tobacco in the composition has a particle size in the range of about 200 μm to about 5 mm, and wherein the ground tobacco composition is contacted with an extraction solvent comprising an aerosol generating agent selected from the group consisting of glycerol, propylene glycol, triacetin and isopropyl myristate.
  • 2. The method of claim 1, wherein at least 90% by weight of the tobacco in the composition has a particle size in the range of about 355 μm to about 3.5 mm.
  • 3. The method of claim 1, wherein at least 95% by weight of the tobacco has a particle size in the range of about 200 μm to about 5 mm.
  • 4. The method of claim 1, the method comprising the steps of: (a) grinding tobacco;(b) removing tobacco particles that are larger than the particle size range using a first sieve; and(c) removing tobacco particles that are smaller than the particle size range using a second sieve.
  • 5. The method of claim 1, wherein at least 97% by weight of the tobacco has a particle size in the range of about 200 μm to about 5 mm.
Priority Claims (1)
Number Date Country Kind
1707758 May 2017 GB national
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2018/062116 5/9/2018 WO
Publishing Document Publishing Date Country Kind
WO2018/210675 11/22/2018 WO A
US Referenced Citations (57)
Number Name Date Kind
RE12994 Gloystein Jul 1909 E
3880172 Anderson et al. Apr 1975 A
4153063 Roselius et al. May 1979 A
4506682 Mueller Mar 1985 A
4561452 Gaehrs Dec 1985 A
4727889 Niven et al. Mar 1988 A
4756318 Clearman et al. Jul 1988 A
5018540 Grubbs et al. May 1991 A
5025812 Fagg et al. Jun 1991 A
5073267 Adda et al. Dec 1991 A
5119835 Heemann et al. Jun 1992 A
5318050 Gonzalez-Parra et al. Jun 1994 A
5435325 Clapp et al. Jul 1995 A
5497792 Prasad et al. Mar 1996 A
5617881 Kossmehl et al. Apr 1997 A
7726320 Robinson et al. Jun 2010 B2
8479747 OConnell Jul 2013 B2
8887737 Howell et al. Nov 2014 B2
9554595 Buchberger Jan 2017 B2
10123560 Rasouli Nov 2018 B2
10375996 Aoun et al. Aug 2019 B2
10426199 Turner et al. Oct 2019 B2
11511056 Hepworth et al. Nov 2022 B2
11612702 Bowen et al. Mar 2023 B2
20040025891 McAdam et al. Feb 2004 A1
20060196517 Gedevanishvili Sep 2006 A1
20070023058 Howell et al. Feb 2007 A1
20070137663 Taylor et al. Jun 2007 A1
20070193595 Haruki et al. Aug 2007 A1
20080257367 Paterno et al. Oct 2008 A1
20090032036 Uematsu et al. Feb 2009 A1
20110159160 Jonsson et al. Jun 2011 A1
20110259353 Coleman et al. Oct 2011 A1
20120006341 Schmekel et al. Jan 2012 A1
20120125354 Byrd et al. May 2012 A1
20120145170 OConnell Jun 2012 A1
20120152265 Dube et al. Jun 2012 A1
20120167901 Onno Jul 2012 A1
20120199145 Byrd et al. Aug 2012 A1
20120318287 Andersen Dec 2012 A1
20130008457 Zheng et al. Jan 2013 A1
20130160777 Murphy Jun 2013 A1
20130239981 Liu et al. Sep 2013 A1
20130255702 Griffith et al. Oct 2013 A1
20140096780 Gerardi Apr 2014 A1
20140190500 Duan et al. Jul 2014 A1
20140238396 Buchberger Aug 2014 A1
20140261483 Hopps Sep 2014 A1
20150027453 Tessmann Jan 2015 A1
20150150305 Shenkal Jun 2015 A1
20150374035 Sanchez et al. Dec 2015 A1
20160081395 Thorens et al. Mar 2016 A1
20160100626 Ishida Apr 2016 A1
20160106144 Muehlbauer Apr 2016 A1
20160205992 Bell et al. Jul 2016 A1
20190320718 Yilmaz et al. Oct 2019 A1
20210106051 Han et al. Apr 2021 A1
Foreign Referenced Citations (219)
Number Date Country
1440699 Sep 2003 CN
1440699 Sep 2003 CN
1459256 Dec 2003 CN
1459256 Dec 2003 CN
1899142 Jan 2007 CN
1899142 Jan 2007 CN
101247739 Aug 2008 CN
101247739 Aug 2008 CN
101338248 Jan 2009 CN
101338248 Jan 2009 CN
101830941 Sep 2010 CN
101830941 Sep 2010 CN
102106602 Jun 2011 CN
102106602 Jun 2011 CN
102199490 Sep 2011 CN
102199490 Sep 2011 CN
102326859 Jan 2012 CN
102326859 Jan 2012 CN
102488318 Jun 2012 CN
102488318 Jun 2012 CN
102640985 Aug 2012 CN
102640985 Aug 2012 CN
102894469 Jan 2013 CN
102894469 Jan 2013 CN
102994228 Mar 2013 CN
102994228 Mar 2013 CN
103060094 Apr 2013 CN
103060094 Apr 2013 CN
103230094 Aug 2013 CN
103230094 Aug 2013 CN
103235066 Aug 2013 CN
103242960 Aug 2013 CN
103242960 Aug 2013 CN
103462206 Dec 2013 CN
103462206 Dec 2013 CN
103468403 Dec 2013 CN
103468403 Dec 2013 CN
103484245 Jan 2014 CN
103484245 Jan 2014 CN
103720030 Apr 2014 CN
103720030 Apr 2014 CN
103783651 May 2014 CN
103783651 May 2014 CN
103783660 May 2014 CN
103783660 May 2014 CN
103235066 Jun 2014 CN
103881817 Jun 2014 CN
103881817 Jun 2014 CN
104489912 Apr 2015 CN
104489912 Apr 2015 CN
105641970 Jun 2016 CN
554139 Jul 1932 DE
554139 Jul 1932 DE
0280817 Sep 1988 EP
0280817 Sep 1988 EP
0323699 Jul 1989 EP
0323699 Jul 1989 EP
0338831 Oct 1989 EP
0338831 Oct 1989 EP
0434333 Jun 1991 EP
0434333 Jun 1991 EP
0443761 Aug 1991 EP
0443761 Aug 1991 EP
0822247 Feb 1998 EP
0822247 Feb 1998 EP
0845220 Jun 1998 EP
0941140 Nov 2002 EP
0941140 Nov 2002 EP
0845220 Sep 2003 EP
1355708 Oct 2003 EP
1355708 Oct 2003 EP
1267650 Dec 2005 EP
1267650 Dec 2005 EP
1815899 Aug 2007 EP
1815899 Aug 2007 EP
1915064 Apr 2008 EP
1915064 Apr 2008 EP
1980163 Oct 2008 EP
1980163 Oct 2008 EP
2303425 Apr 2011 EP
2303425 Apr 2011 EP
2544560 Jan 2013 EP
2544560 Jan 2013 EP
2560509 Feb 2013 EP
2560509 Feb 2013 EP
2008534 Jul 2013 EP
2008534 Jul 2013 EP
2640204 Sep 2013 EP
2640204 Sep 2013 EP
2523568 Dec 2013 EP
2523568 Dec 2013 EP
2727477 May 2014 EP
2727477 May 2014 EP
1951074 Jul 2014 EP
1951074 Jul 2014 EP
2769631 Aug 2014 EP
2769631 Aug 2014 EP
1915064 Apr 2017 EP
1357645 Jun 1974 GB
2173985 Oct 1986 GB
2173985 Oct 1986 GB
2515883 Jan 2015 GB
2515883 Jan 2015 GB
S519838 Jan 1976 JP
S519838 Jan 1976 JP
S62176504 Aug 1987 JP
S62176504 Aug 1987 JP
S63229102 Sep 1988 JP
S63229102 Sep 1988 JP
H0249572 Feb 1990 JP
H0249572 Feb 1990 JP
H03127975 May 1991 JP
H03127975 May 1991 JP
H069986 Jan 1994 JP
H069986 Jan 1994 JP
H0698746 Apr 1994 JP
H0698746 Apr 1994 JP
H07227502 Aug 1995 JP
H07227502 Aug 1995 JP
H0819389 Jan 1996 JP
H0819389 Jan 1996 JP
H0823952 Jan 1996 JP
H0823952 Jan 1996 JP
H0910502 Jan 1997 JP
H0910502 Jan 1997 JP
3014704 Feb 2000 JP
3014704 Feb 2000 JP
3223058 Oct 2001 JP
3223058 Oct 2001 JP
2001276603 Oct 2001 JP
2001276603 Oct 2001 JP
3325028 Sep 2002 JP
3325028 Sep 2002 JP
2005532821 Nov 2005 JP
2005532821 Nov 2005 JP
2007136404 Jun 2007 JP
2007136404 Jun 2007 JP
2008055255 Mar 2008 JP
2008055255 Mar 2008 JP
2009502160 Jan 2009 JP
2009502160 Jan 2009 JP
2014530633 Nov 2014 JP
2014530633 Nov 2014 JP
2017511703 Apr 2017 JP
2017511703 Apr 2017 JP
20170040787 Apr 2017 KR
20170040787 Apr 2017 KR
20170046938 May 2017 KR
20170046938 May 2017 KR
2250717 Apr 2005 RU
2250717 Apr 2005 RU
2250718 Apr 2005 RU
2250718 Apr 2005 RU
2250724 Apr 2005 RU
2250724 Apr 2005 RU
2250734 Apr 2005 RU
2250734 Apr 2005 RU
2250739 Apr 2005 RU
2250739 Apr 2005 RU
9808584 Mar 1998 WO
WO-9808584 Mar 1998 WO
0165954 Sep 2001 WO
WO-0165954 Sep 2001 WO
0226343 Apr 2002 WO
WO-0226343 Apr 2002 WO
2004008888 Jan 2004 WO
WO-2004008888 Jan 2004 WO
2007052159 May 2007 WO
2007053096 May 2007 WO
2007053097 May 2007 WO
2007053098 May 2007 WO
WO-2007052159 May 2007 WO
WO-2007053096 May 2007 WO
WO-2007053097 May 2007 WO
WO-2007053098 May 2007 WO
2008026446 Mar 2008 WO
WO-2008026446 Mar 2008 WO
2009019514 Feb 2009 WO
WO-2009019514 Feb 2009 WO
2009156763 Dec 2009 WO
WO-2009156763 Dec 2009 WO
2011088171 Jul 2011 WO
WO-2011088171 Jul 2011 WO
2011110843 Sep 2011 WO
2011133633 Oct 2011 WO
WO-2011133633 Oct 2011 WO
2012068375 May 2012 WO
2012174677 Dec 2012 WO
WO-2012174677 Dec 2012 WO
2013060827 May 2013 WO
WO-2013060827 May 2013 WO
2013142483 Sep 2013 WO
WO-2013142483 Sep 2013 WO
2013187402 Dec 2013 WO
WO 2013187402 Dec 2013 WO
2014058837 Apr 2014 WO
WO-2014058837 Apr 2014 WO
2014094337 Jun 2014 WO
WO-2014094337 Jun 2014 WO
2015107552 Jul 2015 WO
WO-2015107552 Jul 2015 WO
2015177177 Nov 2015 WO
WO-2015177177 Nov 2015 WO
2016005709 Jan 2016 WO
WO-2016005709 Jan 2016 WO
2016024083 Feb 2016 WO
WO-2016024083 Feb 2016 WO
2016062777 Apr 2016 WO
WO-2016062777 Apr 2016 WO
2016135331 Sep 2016 WO
2016184977 Nov 2016 WO
WO-2016184977 Nov 2016 WO
2018210675 Nov 2018 WO
2018210676 Nov 2018 WO
2018210677 Nov 2018 WO
2018210678 Nov 2018 WO
2018210679 Nov 2018 WO
2018210680 Nov 2018 WO
2018210681 Nov 2018 WO
Non-Patent Literature Citations (50)
Entry
Boiling Points and Structures of Hydrocarbons, Virtual Chembook , Elmhurst College, 2003, [online], retrieved from the Internet, [retrieved Apr. 27, 2022], <URL: chemistry.elmhurst.edu/vchembook/501hcboilingpts.html>. (Year: 2003).
International Search Report and Written Opinion for Application No. PCT/EP2018/062121, dated Jul. 30, 2018, 14 pages.
Marcolli C., et al., “Water Activity in Polyol/Water Systems: New UNIFAC Parameterization,” Atmospheric Chemistry and Physics, Copernicus GMBH, Germany, Retrieved from the Internet: URL: http://www.atmos-chemphys.net/5/1545/2005/acp-5-1545-2005.pdf, [retrieved on Nov. 26, 2014], vol. 5 (6), Jun. 1, 2005, pp. 1545-1555.
Office Action for Japanese Application No. 2019-562889, dated Dec. 8, 2020, 6 pages.
Office Action dated Feb. 2, 2021 for Japanese Application No. 2019-562273, 12 pages.
International Search Report and Written Opinion, Application No. PCT/EP2018/062116, dated Aug. 20, 2018, 22 pages.
“Anonymous: “iFUSE—The Heat not Burn Hybrid—Heat Not Burn,” Jan. 4, 2017 (Jan. 4, 2017), XP055493889. Retrieved from the Internet: URL: https://heatnotburn.co.uk/ifuse-heat-not-burnhybrid/ [retrieved on Jul. 19, 2018]”, pp. 1-15.
“Anonymous: “Where Does the Nicotine Used in Electronic Cigarettes Come From?,” Quora—Aug. 23, 2015 (Aug. 23, 2015), XP055494026”, Retrieved from the Internet: URL: https://www.quora.com/Where-does-the-nicotine-used-in-electronic-cigarettes-come-from, [retrieved on Jul. 19, 2018], 2 pages.
“Application and File History for U.S. Appl. No. 16/614,111, filed Nov. 15, 2019, Inventor Marina Sintyureva.”
“Application and File History for U.S. Appl. No. 16/614,119, filed Nov. 15, 2019, Inventor Helena Digard.”
“Application and File History for U.S. Appl. No. 16/614,267, filed Nov. 15, 2019, Inventor Helena Digard et al.”
“Application and File History for U.S. Appl. No. 16/614,269, filed Nov. 15, 2019, Inventor Helena Digard et al.”
“Application and File History for U.S. Appl. No. 16/614,270, filed Nov. 15, 2019, Inventor Geoff Foss-Smith et al.”
“Application and File History for U.S. Appl. No. 16/614,274, filed Nov. 15, 2019, Inventor Marina Sintyureva.”
“Application and File History for U.S. Appl. No. 16/614,276, filed Nov. 15, 2019, Inventor Marina Sintyureva et al.”
“Boiling Points and Structures of Hydrocarbons”, 2003, [online], Virtual Chembook, Elmhurst College, Retrieved from, http://chemistry.elmhurst.edu/vchembook/501 hcboilingpts.html, on Apr. 27, 2022, 1 page.
“Definition of Through”, Merriam-Webster Dictionary, https://www.merriam-webster.com/dictionary/through, 2022, 9 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062116, dated Nov. 28, 2019”, 8 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062117, dated Nov. 28, 2019”, 8 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062119, dated Nov. 28, 2019”, 8 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062120, dated Nov. 28, 2019”, 9 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062121, dated Nov. 28, 2019”, 8 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062122, dated Nov. 28, 2019”, 9 pages.
“International Preliminary Report on Patentability for Application No. PCT/EP2018/062123, dated Nov. 28, 2019”, 10 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062116, dated Aug. 20, 2018”, 22 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062117, dated Jul. 31, 2018”, 14 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062119, dated Jul. 30, 2018”, 10 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062120, dated Jul. 30, 2018”, 15 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062122, dated Jul. 31, 2018”, 15 pages.
“International Search Report and Written Opinion for Application No. PCT/EP2018/062123, dated Nov. 28, 2018”, 19 pages.
“International Search Report and Written Opinion received for PCT Patent Application No. PCT/EP2018/062121, dated Jul. 30, 2018”, 11 pages.
“Marcolli C., et al., “Water Activity in Polyol/Water Systems: New UNIFAC Parameterization,” Atmospheric Chemistry and Physics, Copernicus GmbH, Germany”, Retrieved from the Internet: URL: http://www.atmos-chemphys.neU5/1545/2005/acp-5-1545-2005.pdf, [retrieved on Nov. 26, 2014], vol. 5 (6), Jun. 1, 2005, pp. 1545-1555.
“Munters., “Sieve Trays,” 2022, Retrieved from the Internet: https://www.munters.com/en/munters/products/mass-transfer/sieve-trays/”, 4 pages.
“Notice of Reasons for Refusal for Japanese Application No. 2019-562269, dated Mar. 2, 2021”, 12 pages.
“Office Action for Canadian Application No. 3,062,987, dated Oct. 7, 2022”, 4 pages.
“Office Action for Japanese Application No. 2019-562270, dated Dec. 8, 2020”, 6 pages.
“Office Action for Japanese Application No. 2019-562289, dated Dec. 8, 2020”, 6 pages.
“Office Action for Japanese Application No. 2019-562304, dated Dec. 1, 2020”, 6 pages.
“Office Action for Japanese Application No. 2019-562384, dated Dec. 1, 2020”, 5 pages.
“Office Action for Korean Application No. 10-2019-7033531, dated Aug. 24, 2021”, 12 pages.
“Office Action for Korean Application No. 10-2019-7033532 dated Feb. 7, 2021”, 9 pages.
“Office Action for Korean Application No. 10-2019-7033534, dated Aug. 24, 2021”, 13 pages.
“Office Action for Korean Application No. 10-2019-7033535, dated Aug. 24, 2021”, 12 pages.
“Office Action for Korean Application No. 10-2019-7033533, dated Aug. 24, 2021”, 12 pages.
“Office Action dated Feb. 2, 2021 for Japanese Application No. 2019-562273”, 24 pages.
“Office Action dated Apr. 24, 2020 for Russian Application No. 2019136484”, 18 pages.
“Office Action dated Dec. 8, 2020 for Japanese Application No. 2019-562289”, 6 pages.
“Search Report for Japanese Application No. 2019-562269, dated Feb. 17, 2021”, 20 pages.
“Tray Column & Tray Types”, Plant operations: Trays Types, 2016, Retrieved from the Internet: http://www.separationprocesses.com/Operations/POT_Chp02a.htm, 2 pages.
“Search Report received for Chinese Patent Application No. 201880032692.4, dated Jun. 25, 2021”, 1 page (English Translation Only).
Related Publications (1)
Number Date Country
20200146334 A1 May 2020 US