DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on February 20, 2026 has been entered.
Status of the Claims
Claims 16-34 are pending and are subject to this Office Action. Claims 16, 30, and 34 are amended. Claims 1-15 are cancelled.
Response to Amendments
The amendments to the claims filed on February 20, 2026 are acknowledged.
Response to Arguments
Applicant's arguments, see pgs 7-14, filed February 20, 2026, with respect to the rejection(s) of claims 16-34 under 35 U.S.C. 103 have been fully considered but they are not persuasive.
On pg. 10, Applicant argues that Sensabaugh does not disclose a composition comprising between about 5 percent by weight and about 20 percent by weight of water. On pg. 11, Applicant argues that Karles does not disclose a method wherein the heating step is carried out for at least 90 minutes under a flow of an inert gas, or a composition having a first ratio by weight of (β-ionone + β-damascenone) to (phenol) of greater than 0.25; and a second ratio by weight of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) of greater than 5 x 10-4. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). As applied to Claim 30 on the Final Rejection dated 10/23/2025, Sensabaugh has been combined with Karles to yield a composition comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition.
Specifically, Karles teaches a nicotine composition ([0003]-[0004], [0054]), comprising: an extract of tobacco volatiles obtained by heating a natural tobacco material ([0003]-[0004]; In the process of the invention, tobacco is heated such that tobacco volatiles evolve from the tobacco. The volatiles are collected and combined with a pre-vapor formulation); and
a non-aqueous solvent ([00049]-[0050], Propylene glycol and glycerin are non-aqueous solvents),
wherein the nicotine composition further comprises between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent ([0049]-[0050], The pre-vapor formulation may comprise one or more vapor formers (glycerin, propylene glycol, non-aqueous solvents) at 40%-90% by weight)
between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition ([0051], The pre-vapor formulation comprises water at 5%-40% by weight).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to configure the nicotine composition of Sensabaugh for use as a pre-vapor formulation in an electronic cigarette as taught by Karles because Sensabaugh and Karles are directed to nicotine compositions, and Karles demonstrates that a nicotine composition comprising volatiles from natural tobacco heated between 100 degrees Celsius and 160 degrees Celsius is suitable for use as a pre-vapor formulation in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054]).
Further, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide the nicotine composition taught by Sensabaugh further comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition because Karles demonstrates that the composition may be used in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054] as applied above), and Karles demonstrates that including the non-aqueous solvent and water within the claimed ranges is preferable for a pre-vapor formulation (Karles, [0049]-[0051]).
On pg. 11-13, Applicant argues that the teaching of Karles is incompatible with the teaching of Sensabaugh because Karles discloses a pre-vapor formulation comprising 5-40% water by weight Karles, [0051]), while Sensabaugh states that the process comprises reducing a moisture content of a tobacco starting material to an amount lower than 4% by weight. Examiner does not find the argument persuasive because Karles states that an extract comprising evolved volatiles from a tobacco material can be combined with water and another solvent to yield a pre vapor formulation (Karles, [0027]-[0028]). While Sensabaugh states that moisture reduction is preferable during the extraction process, Sensabaugh does not explicitly state that the extract cannot be combined with water to form a pre vapor formulation. As the combination argued on the final rejection only requires the addition of water and the adjustment of the non-aqueous solvent and water amounts, the proposed modification of Sensabaugh in view of Karles does not require changing the process of Sensabaugh. Therefore, obvious to one of ordinary skill in the art would have been motivated by the disclosures of Karles to provide the nicotine composition taught by Sensabaugh further comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition because Karles demonstrates that a nicotine composition comprising volatiles from natural tobacco heated between 100 degrees Celsius and 160 degrees Celsius is suitable for use as a pre-vapor formulation in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054]) and Karles demonstrates that including the non-aqueous solvent and water within the claimed ranges is preferable for a pre-vapor formulation (Karles, [0049]-[0051]). As such, the arguments are found unpersuasive.
The following is a modified rejection based on amendments made to the claims.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 16-31, and 34 are rejected under 35 U.S.C. 103 as being unpatentable over Sensabaugh (US 5,235,992 A, cited on the IDS dated 3/1/2022) in view of Karles (US 2017/0245543 A1), as evidenced by Pontes (US 2020/0187551 A1), Fernando (US 2015/0359264 A1), Besso (US 2017/0273351 A1), White-841 (US 6,591,841 B1), and White-404 (US 6,048,404 A).
Regarding Claim 16, Sensabaugh, directed to tobacco extracts and nicotine compositions (col 2, ln 28-37, The invention is directed to flavor substances extracted from tobacco; and col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition), teaches a nicotine composition (col 2, ln 28-37, The invention is directed to extracted tobacco flavor substances; and col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition), comprising:
an extract of tobacco volatiles collected from a gas stream obtained by heating a natural tobacco material at a temperature of from 125°C to 140°C for at least 90 minutes under flow of an inert gas (col 2, ln 54-61, col 3, ln 32-39, col 4, ln 4-66; In the process of the invention, tobacco is heated at two different temperatures differing by 50° C under the flow of an inert carrier gas such that tobacco volatiles evolve from the tobacco. The first extraction temperature may preferably be between 100° C and 225° C. Volatiles evolved from tobacco may be collected by bubbling the carrier gas comprising the volatiles though a liquid sorbent. The volatiles are collected to form an extract of tobacco flavor substances; and col 8, ln 7-46, Example 6 shows that the tobacco is held at the first extraction temperature for 3.5 hours, then raised to the second extraction temperature for 3 hours);
water (col 4, ln 13-21; The tobacco starting material may undergo a moisture reduction process to a value less than about 4%. Residual water may remain in the extract); and
a non-aqueous solvent (col 4, ln 4-10, Volatiles evolved from tobacco may be collected by bubbling the carrier gas comprising the volatiles though a liquid sorbent such as propylene glycol; and col 5, ln 50-59, the flavor substances yielded from the bubbling step may be retained in the liquid sorbent, and incorporated into a smoking article),
wherein the natural tobacco material is not subjected to any treatment adapted to alter the pH of the natural tobacco (col 4, ln 13 – col 6, ln 19 describe the process of the invention in detail. Sensabaugh does not mention altering the pH of the natural tobacco),
a content of nicotine is at least 0.2 percent by weight based on the weight of the nicotine composition (col 13, ln 14-35, Examples 11 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition. The nicotine comprises an extract from flue cured tobacco at 1.00g, Turkish at 1.00g, Latakia at 1.00g, Burley at 1.00g, nicotine at 0.60g, and malic acid at 0.20g. Based on these masses, the content of nicotine is 12.5% by weight of-nicotine based on the weight of the nicotine composition);
prepared by a method comprising the steps of: preparing a natural tobacco starting material (col 4, ln 13-34; Natural tobacco is prepared for the process by reducing its moisture content without removing volatile flavor components);
heating the tobacco starting material under flow of an inert gas at an extraction temperature of between 125 degrees Celsius and 140 degrees Celsius for at least 90 minutes to distill volatile compounds from the tobacco starting material (col 4, ln 35-66; The tobacco is then heated at two different toasting (extraction) temperatures differing by 50° C to distill volatile flavor substances (compounds) from the tobacco starting material. The first extraction temperature may preferably be between 100° C and 225° C; and col 8, ln 7-46, Example 6 shows that the tobacco is held at the first extraction temperature for 3.5 hours, then raised to the second extraction temperature for 3 hours; and col 3, ln 32-39, Sensabaugh further states that extraction may be performed a temperature range of 100° C to 350° C. Therefore, the first heating temperature may be 100° C, and the second heating temperature may by 150° C, for example. An inert carrier gas flows during the heating process such that the volatile gases are removed from the heating chamber);
collecting the volatile compounds released from the tobacco starting material during the heating under flow of the inert gas (col 3, ln 32-39, col 4, ln 60-66; An inert carrier gas flows during the heating (extraction) process such that the volatile gases are collected and removed from the heating chamber);
forming a liquid tobacco extract comprising the collected volatile compounds (col 5, ln 33-59, The flavor substances (collected volatiles compounds) are separately collected by passing the flowing gas stream sequentially through 1) a moderate temperature trap, 2) a cold temperature trap, and 3) a filter capable of collecting submicron sized aerosol particles. One or both of the moderate or cold temperature trap may comprise a liquid sorbent such as propylene glycol, and the gas stream may be bubbled through the liquid sorbent to collect the volatile compounds. The liquid sorbent comprising the volatile compounds is the liquid tobacco extract); and
forming the nicotine composition from the liquid tobacco extract (col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances (liquid tobacco extract) may be combined with nicotine to form a nicotine composition)
wherein the natural tobacco starting material is not subjected to any treatment adapted to alter the pH of the natural tobacco (col 4, ln 13 – col 6, ln 19 describe the process of the invention in detail. Sensabaugh does not mention altering the pH of the natural tobacco),
but does not teach the composition comprising: i) between about 80 percent by weight and about 95 percent by weight of the non-aqueous solvent and between about 5 percent by weight and about 20 percent by weight of water based upon the weight of the nicotine composition, ii) a first ratio by weight of (β-ionone + β-damascenone) to (phenol) of greater than 0.25; and a second ratio by weight of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) of greater than 5 x 10-4.
With respect to i), Karles, directed to nicotine compositions ([0001]-[0004], [0054], The pre-vapor formulation comprises nicotine), teaches a nicotine composition ([0003]-[0004], [0054], The invention is directed to a pre-vapor formulation. Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight), comprising:
an extract of tobacco volatiles obtained by heating a natural tobacco material ([0003]-[0004]; In the process of the invention, tobacco is heated such that tobacco volatiles evolve from the tobacco. The volatiles are collected and combined with a pre-vapor formulation); and
a non-aqueous solvent ([00049]-[0050], Propylene glycol and glycerin are non-aqueous solvents),
a content of nicotine is at least 0.2 percent by weight based on the weight of the nicotine composition ([0054], Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight);
prepared by a method comprising the steps of: preparing a natural tobacco starting material ([0004], [0032]-[0033], Fig. 2; Natural tobacco is mixed with at least one additive at step 75);
heating the tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius to distill volatile compounds from the tobacco starting material ([0004], [0032]-[0034], Fig. 2; At step 100, the tobacco starting material is heated to at temperature between 50° C to 250° C to distill volatile compounds from the tobacco starting material);
collecting the volatile compounds released from the tobacco starting material during the heating ([0004], [0046]; At step 200, the volatile compounds released from the tobacco starting material during the heating are collected);
forming a liquid tobacco extract comprising the collected volatile compounds ([0004], [0047]-[0051]; At step 300, the method also includes collecting 200 volatiles from the heated tobacco material and combining 300 the volatiles with a pre-vapor formulation immediately after the collecting step 200. The pre-vapor formulation includes liquid components such as propylene glycol, glycerin, and/or water); and
forming the nicotine composition from the liquid tobacco extract ([0004], [0047]-[0051]; The composition resulting from combining the volatiles with the pre-vapor formulation is the nicotine composition)
wherein the natural tobacco starting material is not subjected to any treatment adapted to alter the pH of the natural tobacco ([0005], [0009], The pH of the natural tobacco may optionally be altered; however, there must necessarily be embodiments of the invention which do not alter the pH of the natural tobacco),
wherein the nicotine composition is suitable for use as a pre-vapor formulation in an electronic cigarette ([0026]),
wherein the nicotine composition further comprises between about 80 percent by weight and about 95 percent by weight of the non-aqueous solvent ([0049]-[0050], The pre-vapor formulation may comprise one or more vapor formers (glycerin, propylene glycol, non-aqueous solvents) at 40%-90% by weight) and
between about 5 percent by weight and about 20 percent by weight of water, based on the weight of the nicotine composition ([0051], The pre-vapor formulation comprises water at 5%-40% by weight.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to configure the nicotine composition of Sensabaugh for use as a pre-vapor formulation in an electronic cigarette as taught by Karles because Sensabaugh and Karles are directed to nicotine compositions, and Karles demonstrates that a nicotine composition comprising volatiles from natural tobacco heated between 100 degrees Celsius and 160 degrees Celsius is suitable for use as a pre-vapor formulation in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054]).
Further, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide the nicotine composition taught by Sensabaugh further comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition because Karles demonstrates that the composition may be used in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054] as applied above), and Karles demonstrates that including the non-aqueous solvent and water within the claimed ranges is preferable for a pre-vapor formulation (Karles, [0049]-[0051]).
With respect to ii), Pontes, directed to tobacco extracts ([0001]), demonstrates that β-ionone, β-damascenone, furaneol, and substituted pyrazines are volatiles which can evolve from heating a tobacco material ([0074]).
Fernando, directed to nicotine compositions ([0001]), demonstrates that phenol is a volatile which can evolve from heating a tobacco material ([0013]).
Besso, directed to tobacco extracts ([0001]), demonstrates that substituted pyrazines are volatiles which can evolve from heating a tobacco material ([0023]-[0024]).
It would have been obvious to one of ordinary skill in the art to provide the composition taught by Sensabaugh comprising phenol and 2,3-diethyl-5-methylpyrazine because β-ionone, β-damascenone, furaneol, phenol, and various substituted pyrazines are volatiles which can evolve from heating a tobacco material (Pontes, [0074]; and Fernando, [0013]; and Besso, [0023]-[0024]). Therefore, one of ordinary skill would reasonably expect a nicotine composition prepared by the method taught by Sensabaugh to comprise β-ionone, β-damascenone, furaneol, phenol, and 2,3-diethyl-5-methylpyrazine. Further, because Sensabaugh teaches the nicotine composition prepared by the method claimed in Claim 34, and the Applicant discloses that the method results in an equivalent nicotine composition as claim 1, one of ordinary skill would reasonably expect the nicotine composition of the prior art to have a first ratio by weight of (β-ionone + β-damascenone) to (phenol) of greater than 0.25, and a second ratio by weight of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) of greater than 5 x 10-4 as claimed, absent evidence to the contrary.
The ranges for the nicotine amount, non-aqueous solvent amount, and the water amount disclosed by the prior art overlap the claimed ranges, and therefore the claimed ranges are considered prima facie obvious. See MPEP § 2144.05.I.
Regarding Claim 17-21, Because Sensabaugh in view of Karles teaches the nicotine composition prepared by the method claimed in Claim 34, the Applicant discloses that the method results in an equivalent nicotine composition as claim 1 having overlapping ratios, and the specification discloses that the method results in the claimed ratios, one of ordinary skill would reasonably expect the nicotine composition of the prior art to provide the first ratio by weight greater than 0.5, 1, 1.5, 2, and between 2 and 10, absent evidence to the contrary, since the composition of the prior art is equivalent to the claimed composition.
Regarding Claim 22, Because Sensabaugh in view of Karles teaches the nicotine composition prepared by the method claimed in Claim 34, the Applicant discloses that the method results in an equivalent nicotine composition as claim 1 having overlapping ratios, and the specification discloses that the method results in the claimed ratios, one of ordinary skill would reasonably expect the nicotine composition of the prior art to provide the second ratio by weight between 8 x 10-4 and 9 x 10-3, absent evidence to the contrary, since the composition of the prior art is equivalent to the claimed composition.
Regarding Claim 23, Sensabaugh in view of Karles teaches the nicotine composition according to claim 16, but does not teach the composition wherein the nicotine composition comprises between 0.4 percent by weight and 3.6 percent by weight nicotine based on the weight of the nicotine composition.
The precise percent by weight nicotine based on the weight of the nicotine composition would have been considered a result effective variable by one of ordinary skill in the art before the effective filing date of the invention because the flavor, harshness, taste, and mouth feel of the nicotine composition is a variable which can be modified by the amount of the nicotine (Sensabaugh, col 14, ln 15-55). As such, without showing unexpected results, the claimed nicotine amount cannot be considered critical. Accordingly, one of ordinary skill in the art before the effective filing date of the invention would have optimized the nicotine amount by routine experimentation to obtain the desired flavor, harshness, taste, and mouth feel, since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. The discovery of an optimum value of a known result effective variable, without producing any new or unexpected results, is within the ambit of a person of ordinary skill in the art (see MPEP § 2144.05, II).
Regarding Claim 24, Sensabaugh in view of Karles does not teach the nicotine composition according to claim 16 further comprising a third ratio by weight of (β-ionone + β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N- nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)), wherein the third ratio by weight is greater than 1.5.
Pontes, directed to tobacco extracts ([0001]), demonstrates that β-ionone and β-damascenone are volatiles which can evolve from heating a tobacco material ([0074]),
demonstrates that β-ionone and β-damascenone are volatile compounds of interest which responsible for a characteristic taste or flavour ([0034]-[0037], [0074]-[0075], [0087]),
and demonstrates that tobacco specific nitrosamines are undesirable for a tobacco extract (0076]).
Fernando, directed to nicotine compositions ([0001]), demonstrates that 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R, S)-N-nitrosoanatabine, (R, S)-N-nitrosoanabasine, and N-nitrosonornicotine are volatiles which can evolve from heating a tobacco material ([0013]), and are potentially harmful constituents to a smoker ([0012]-[0013]).
White-841, directed to tobacco extraction (col 2, ln 32-67), demonstrates that 2-furanmethanol is a volatile which can evolve from heating a tobacco material (col 8, ln 31-67, Table 1, Row 17 (2-furanmethanol)).
It would have been obvious to one of ordinary skill in the art to provide the composition taught by Sensabaugh comprising β-ionone, β-damascenone, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R, S)-N-nitrosoanatabine, (R, S)-N- nitrosoanabasine, N-nitrosonornicotine, and 2-furanmethanol because said compounds are volatiles which can be extracted from tobacco material (Pontes, [0074]; and Fernando, [0013]; and White-841, col 8, ln 31-67, Table 1, Row 17 (2-furanmethanol)). Because Sensabaugh teaches the nicotine composition prepared by the method claimed in Claim 34, the Applicant discloses that the method results in an equivalent nicotine composition as claim 1 having overlapping ratios, and the specification discloses that the method results in the claimed ratios, one of ordinary skill would reasonably expect the nicotine composition of the prior art to have a third ratio by weight of (β-ionone + β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N- nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)) greater than 1.5, absent evidence to the contrary, since the composition of the prior art is equivalent to the claimed composition. Additionally, one would have been motivated to maximize the value of the third ratio to a value above 1.5 because β-ionone and β-damascenone are volatile compounds of interest for a tobacco extract because they contribute to the tobacco flavor (Pontes, [0034]-[0037], [0074]-[0075], [0087]; β-ionone are β-damascenone are listed as volatile compounds of interest extracted from the tobacco material and provided in the tobacco extract). Further, tobacco specific nitrosamines such as 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R, S)-N-nitrosoanatabine, (R, S)-N- nitrosoanabasine, and N-nitrosonornicotine are known in the art to be potentially harmful constituents (Fernando, [0013]), and further tobacco specific nitrosamines are undesirable for a tobacco extract (Pontes, [0076).
Regarding Claim 25, Sensabaugh in view of Karles teaches the nicotine composition according to claim 16. Sensabaugh further teaches the composition wherein the extract of tobacco volatiles is derived from Burley tobacco and Bright tobacco (col 3, ln 25-31, The extract can be derived from Burley, Flue-Cured, and/or Turkish tobacco. Flue-Cured and Turkish (Oriental) tobacco are forms of Bright tobacco; see instant specification pg 33, ln ln 33-34).
Regarding Claim 26, Sensabaugh in view of Karles teaches the nicotine composition according to claim 25. Sensabaugh further teaches the composition wherein the Bright tobacco is one or more of Oriental tobacco and flue-cured tobacco (col 3, ln 25-31, The extract can be derived from Burley, Flue-Cured, and/or Turkish (Oriental) tobacco).
Regarding Claim 27, Sensabaugh in view of Karles teaches the nicotine composition according to claim 25. Sensabaugh further teaches the composition wherein the non-aqueous solvent is glycerine, propylene glycol, triacetin, 1,3-propanediol, or a mixture thereof (col 4, ln 4-10, Volatiles evolved from tobacco may be collected by bubbling the carrier gas comprising the volatiles though a liquid sorbent such as propylene glycol; and col 5, ln 50-59, the flavor substances yielded from the bubbling step may be retained in the liquid sorbent, and incorporated into a smoking article).
Regarding Claim 28, Sensabaugh in view of Karles does not explicitly teach the nicotine composition according to claim 16 further comprising one or more of acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenylethanol, eugenol, and sotolone.
White-404, directed to tobacco extraction (col 2, ln 29-67), demonstrates that acetic acid is a volatile which can evolve from heating a tobacco material (col 7, ln 51-67).
It would have been obvious to one of ordinary skill in the art to provide the composition taught by Sensabaugh comprising acetic acid because acetic acid is a volatile which can be extracted from tobacco material (White-404, col 7, ln 51-67). Because Sensabaugh teaches the nicotine composition prepared by the method claimed in Claim 34, the Applicant discloses that the method results in an equivalent nicotine composition as claim 1 having overlapping ratios, and the specification discloses that the method results in the claimed ratios, one of ordinary skill would reasonably expect the nicotine composition of the prior art to include acetic acid.
Regarding Claim 29, Sensabaugh in view of Karles does not explicitly teach the nicotine composition according to claim 16 wherein the nicotine composition comprises at least 300 micrograms of acetic acid per gram of the nicotine composition.
White-404, directed to tobacco extraction (col 2, ln 29-67), demonstrates that acetic acid is a volatile which can evolve from heating a tobacco material (col 7, ln 51-67), and Flue-cured tobacco and Oriental tobacco are known to release large amounts of acetic acid (White-404, col 7, ln 51-61, Figs. 1-3; Flue-cured and Turkish tobacco release large amounts of acetic acid. Turkish tobacco is commonly referred to as Oriental tobacco).
It would have been obvious to one of ordinary skill in the art to provide the composition taught by Sensabaugh in view of Karles comprising acetic acid because acetic acid is a volatile which can be extracted from tobacco material (White-404, col 7, ln 51-67). Because Sensabaugh teaches the nicotine composition prepared by the method claimed in Claim 34, and the specification discloses that the method results in the claimed ratios, one of ordinary skill would reasonably expect the nicotine composition of the prior art to include acetic acid. Additionally, Flue-cured tobacco and Oriental Tobacco are known to release large amounts of acetic acid (White-404, col 7, ln 51-61, Figs. 1-3; Flue-cured and Turkish tobacco release large amounts of acetic acid. Turkish tobacco is commonly referred to as Oriental tobacco), and Sensabaugh lists Flue-cured tobacco and Oriental tobacco as preferred tobacco starting material to form the nicotine composition (Sensabaugh, col 3, ln 25-31, The extract can be derived from Burley, Flue-Cured, and/or Turkish (Oriental) tobacco). Therefore, the amount of acetic acid released from the tobacco material can be optimized via the selection of the type of tobacco used as the starting material in order to achieve a desired flavor profile.
Regarding Claim 30, Sensabaugh in view of Karles teaches the nicotine composition according to claim 27. Sensabaugh further teaches the composition wherein the content of the non-aqueous solvent is between about 80 percent by weight and about 90 percent by weight ([0049]-[0050], The pre-vapor formulation may comprise one or more vapor formers (glycerin, propylene glycol, non-aqueous solvents) at 40%-90% by weight) and
the content of the water is between about 10 percent by weight and about 15 percent by weight, based on the weight of the nicotine composition ([0051], The pre-vapor formulation comprises water at 5%-40% by weight).
The ranges for the non-aqueous solvent amount and the water amount disclosed by the prior art overlap the claimed ranges, and therefore the claimed ranges are considered prima facie obvious. See MPEP § 2144.05.I.
Regarding Claim 31, Sensabaugh in view of Karles teaches the nicotine composition according to claim 25. Sensabaugh further teaches the composition wherein the nicotine composition is a liquid nicotine composition (col 4, ln 4-10, Volatiles evolved from tobacco may be collected by bubbling the carrier gas comprising the volatiles though a liquid sorbent such as propylene glycol; and col 5, ln 50-59, the flavor substances yielded from the bubbling step may be retained in the liquid sorbent, and incorporated into a smoking article; and col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition. Therefore, the nicotine composition is provided in liquid form).
Regarding Claim 34, Sensabaugh, directed to tobacco extracts and nicotine compositions (col 2, ln 28-37, The invention is directed to flavor substances extracted from tobacco; and col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition), teaches a nicotine composition (col 2, ln 28-37, The invention is directed to extracted tobacco flavor substances; and col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition), comprising:
an extract of tobacco volatiles obtained by heating a natural tobacco material under flow of an inert gas (col 2, ln 54-61, col 3, ln 32-39, col 4, ln 13-63; In the process of the invention, tobacco is heated at an elevated temperature under the flow of an inert carrier gas such that tobacco volatiles evolve from the tobacco. The volatiles are collected and condensed to form an extract of tobacco flavor substances); and
a non-aqueous solvent (col 4, ln 4-10, Volatiles evolved from tobacco may be collected by bubbling the carrier gas comprising the volatiles though a liquid sorbent such as propylene glycol; and col 5, ln 50-59, the flavor substances yielded from the bubbling step may be retained in the liquid sorbent, and incorporated into a smoking article),
water (col 4, ln 13-21; The tobacco starting material may undergo a moisture reduction process to a value less than about 4%. Residual water may remain in the extract), and
nicotine (col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances may be combined with nicotine to form a nicotine composition),
wherein the nicotine composition is obtained by a method comprising: preparing a natural tobacco starting material (col 4, ln 13-34; Natural tobacco is prepared for the process by reducing its moisture content without removing volatile flavor components);
heating the tobacco starting material under flow of an inert gas at an extraction temperature of between 125 degrees Celsius and 140 degrees Celsius for at least 90 minutes to distill volatile compounds from the tobacco starting material to obtain a distillate gas stream (col 4, ln 35-66; The tobacco is then heated at two different toasting (extraction) temperatures differing by 50° C to distill volatile flavor substances (compounds) from the tobacco starting material. The first extraction temperature may preferably be between 100° C and 225° C; and col 8, ln 7-46, Example 6 shows that the tobacco is held at the first extraction temperature for 3.5 hours, then raised to the second extraction temperature for 3 hours; and col 3, ln 32-39, Sensabaugh further states that extraction may be performed a temperature range of 100° C to 350° C. Therefore, the first heating temperature may be 100° C, and the second heating temperature may by 150° C, for example. An inert carrier gas flows during the heating process such that the volatile gases are removed from the heating chamber. The volatile gases are the distillate gas stream);
collecting the volatile compounds released from the tobacco starting material during the heating under flow of the inert gas from the distillate gas stream (col 3, ln 32-39, col 4, ln 60-66, col 5, ln 33-59; An inert carrier gas flows during the heating (extraction) process such that the volatile gases (distillate gas stream) are collected and removed from the heating chamber. The flavor substances (volatile compounds) are separately collected by passing the flowing gas stream sequentially through 1) a moderate temperature trap, 2) a cold temperature trap, and 3) a filter capable of collecting submicron sized aerosol particles.);
forming a liquid tobacco extract comprising the collected volatile compounds (col 5, ln 33-59, The flavor substances (collected volatile compounds) are separately collected by passing the flowing gas stream sequentially through 1) a moderate temperature trap, 2) a cold temperature trap, and 3) a filter capable of collecting submicron sized aerosol particles. One or both of the moderate or cold temperature trap may comprise a liquid sorbent such as propylene glycol, and the gas stream may be bubbled through the liquid sorbent to collect the volatile compounds. The liquid sorbent comprising the volatile compounds is the liquid tobacco extract); and
forming the nicotine composition from the liquid tobacco extract (col 13, ln 14 – col 14, ln 21, Examples 11 and 14 demonstrate that the extracted tobacco flavor substances (liquid tobacco extract) may be combined with nicotine to form a nicotine composition)
wherein the natural tobacco starting material is not subjected to any treatment adapted to alter the pH of the natural tobacco (col 4, ln 13 – col 6, ln 19 describe the process of the invention in detail. Sensabaugh does not mention altering the pH of the natural tobacco),
but does not teach the composition comprising i) between about 80 percent by weight and about 95 percent by weight of the non-aqueous solvent and between about 5 percent by weight and about 20 percent by weight of water based upon the weight of the nicotine composition, ii) wherein the nicotine composition has a first ratio by weight of (β-ionone + β-damascenone) to (phenol) of greater than 0.25; and a second ratio by weight of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) of greater than 5 x 10-4.
With respect to i), Karles, directed to nicotine compositions ([0001]-[0004], [0054], The pre-vapor formulation comprises nicotine), teaches a nicotine composition ([0003]-[0004], [0054], The invention is directed to a pre-vapor formulation. Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight), comprising:
an extract of tobacco volatiles obtained by heating a natural tobacco material ([0003]-[0004]; In the process of the invention, tobacco is heated such that tobacco volatiles evolve from the tobacco. The volatiles are collected and combined with a pre-vapor formulation); and
a non-aqueous solvent ([00049]-[0050], Propylene glycol and glycerin are non-aqueous solvents),
a content of nicotine is at least 0.2 percent by weight based on the weight of the nicotine composition ([0054], Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight);
prepared by a method comprising the steps of: preparing a natural tobacco starting material ([0004], [0032]-[0033], Fig. 2; Natural tobacco is mixed with at least one additive at step 75);
heating the tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius to distill volatile compounds from the tobacco starting material ([0004], [0032]-[0034], Fig. 2; At step 100, the tobacco starting material is heated to at temperature between 50° C to 250° C to distill volatile compounds from the tobacco starting material);
collecting the volatile compounds released from the tobacco starting material during the heating ([0004], [0046]; At step 200, the volatile compounds released from the tobacco starting material during the heating are collected);
forming a liquid tobacco extract comprising the collected volatile compounds ([0004], [0047]-[0051]; At step 300, the method also includes collecting 200 volatiles from the heated tobacco material and combining 300 the volatiles with a pre-vapor formulation immediately after the collecting step 200. The pre-vapor formulation includes liquid components such as propylene glycol, glycerin, and/or water); and
forming the nicotine composition from the liquid tobacco extract ([0004], [0047]-[0051]; The composition resulting from combining the volatiles with the pre-vapor formulation is the nicotine composition)
wherein the natural tobacco starting material is not subjected to any treatment adapted to alter the pH of the natural tobacco ([0005], [0009], The pH of the natural tobacco may optionally be altered; however, there must necessarily be embodiments of the invention which do not alter the pH of the natural tobacco),
wherein the nicotine composition is suitable for use as a pre-vapor formulation in an electronic cigarette ([0026]),
wherein the nicotine composition further comprises between about 80 percent by weight and about 95 percent by weight of the non-aqueous solvent ([0049]-[0050], The pre-vapor formulation may comprise one or more vapor formers (glycerin, propylene glycol, non-aqueous solvents) at 40%-90% by weight) and
between about 5 percent by weight and about 20 percent by weight of water, based on the weight of the nicotine composition ([0051], The pre-vapor formulation comprises water at 5%-40% by weight).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to configure the nicotine composition of Sensabaugh for use as a pre-vapor formulation in an electronic cigarette as taught by Karles because Sensabaugh and Karles are directed to nicotine compositions, and Karles demonstrates that a nicotine composition comprising volatiles from natural tobacco heated between 100 degrees Celsius and 160 degrees Celsius is suitable for use as a pre-vapor formulation in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054]).
Further, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide the nicotine composition taught by Sensabaugh further comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition because Karles demonstrates that the composition may be used in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054] as applied above), and Karles demonstrates that including the non-aqueous solvent and water within the claimed ranges is preferable for a pre-vapor formulation (Karles, [0049]-[0051]).
With respect to ii), Pontes, directed to tobacco extracts ([0001]), demonstrates that β-ionone, β-damascenone, furaneol, and substituted pyrazines are volatiles which can evolve from heating a tobacco material ([0074]).
Fernando, directed to nicotine compositions ([0001]), demonstrates that phenol is a volatile which can evolve from heating a tobacco material ([0013]).
Besso, directed to tobacco extracts ([0001]), demonstrates that substituted pyrazines are volatiles which can evolve from heating a tobacco material ([0023]-[0024]).
It would have been obvious to one of ordinary skill in the art to provide the composition taught by Sensabaugh comprising phenol and 2,3-diethyl-5-methylpyrazine because β-ionone, β-damascenone, furaneol, phenol, and various substituted pyrazines are volatiles which can evolve from heating a tobacco material (Pontes, [0074]; and Fernando, [0013]; and Besso, [0023]-[0024]). Therefore, one of ordinary skill would reasonably expect a nicotine composition prepared by the method taught by Sensabaugh to comprise β-ionone, β-damascenone, furaneol, phenol, and 2,3-diethyl-5-methylpyrazine. Further, because Sensabaugh teaches the nicotine composition prepared by the method claimed in Claim 34, and the Applicant discloses that the method results in an equivalent nicotine composition as claim 1 having the claimed ratios, which the Applicant has disclosed results in an equivalent nicotine composition as claim 1, one of ordinary skill would reasonably expect the nicotine composition of the prior art to have a first ratio by weight of (β-ionone + β-damascenone) to (phenol) of greater than 0.25, and a second ratio by weight of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) of greater than 5 x 10-4 as claimed, absent evidence to the contrary.
The ranges for the nicotine amount, the non-aqueous solvent amount, the extraction temperature, and the extraction time disclosed by the prior art overlap the claimed ranges, and therefore the claimed ranges are considered prima facie obvious. See MPEP § 2144.05.I.
Claims 32-33 are rejected under 35 U.S.C. 103 as being unpatentable over Sensabaugh (US 5,235,992 A, cited on the IDS dated 3/1/2022) in view of Karles (US 2017/0245543 A1) as applied to Claim 16, and further in view of Dayioglu (US 2019/0200679 A1).
Regarding Claims 32-33, Sensabaugh in view of Karles does not teach the nicotine composition according to claim 16 wherein the nicotine composition is a gel nicotine composition. Sensabaugh in view of Karles does not teach a cartridge comprising the nicotine composition of claim 16.
Karles, directed to nicotine compositions ([0001]-[0004], [0054], The pre-vapor formulation comprises nicotine), teaches a nicotine composition ([0003]-[0004], [0054], The invention is directed to a pre-vapor formulation. Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight), comprising:
an extract of tobacco volatiles obtained by heating a natural tobacco material ([0003]-[0004]; In the process of the invention, tobacco is heated such that tobacco volatiles evolve from the tobacco. The volatiles are collected and combined with a pre-vapor formulation); and
a non-aqueous solvent ([00049]-[0050], Propylene glycol and glycerin are non-aqueous solvents),
a content of nicotine is at least 0.2 percent by weight based on the weight of the nicotine composition ([0054], Nicotine is included in the pre-vaporization formulation in an amount ranging from about 2% by weight to about 6% by weight);
prepared by a method comprising the steps of: preparing a natural tobacco starting material ([0004], [0032]-[0033], Fig. 2; Natural tobacco is mixed with at least one additive at step 75);
heating the tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius to distill volatile compounds from the tobacco starting material ([0004], [0032]-[0034], Fig. 2; At step 100, the tobacco starting material is heated to at temperature between 50° C to 250° C to distill volatile compounds from the tobacco starting material);
collecting the volatile compounds released from the tobacco starting material during the heating ([0004], [0046]; At step 200, the volatile compounds released from the tobacco starting material during the heating are collected);
forming a liquid tobacco extract comprising the collected volatile compounds ([0004], [0047]-[0051]; At step 300, the method also includes collecting 200 volatiles from the heated tobacco material and combining 300 the volatiles with a pre-vapor formulation immediately after the collecting step 200. The pre-vapor formulation includes liquid components such as propylene glycol, glycerin, and/or water); and
forming the nicotine composition from the liquid tobacco extract ([0004], [0047]-[0051]; The composition resulting from combining the volatiles with the pre-vapor formulation is the nicotine composition)
wherein the natural tobacco starting material is not subjected to any treatment adapted to alter the pH of the natural tobacco ([0005], [0009], The pH of the natural tobacco may optionally be altered; however, there must necessarily be embodiments of the invention which do not alter the pH of the natural tobacco),
wherein the nicotine composition is a gel nicotine composition ([0028]),
wherein the nicotine composition is suitable for use as a pre-vapor formulation in an electronic cigarette ([0026]).
Dayioglu, directed to nicotine compositions ([0008], The cartridge comprises a nicotine composition), teaches a cartridge comprising a nicotine composition ([0008], The cartridge comprises a nicotine composition),
wherein the nicotine composition is a gel nicotine composition ([0044], [0106]),
wherein the composition is less likely to leak from an electronic cigarette if it is provided as a gel composition instead of a liquid composition ([0044]).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to configure the nicotine composition of Sensabaugh for use as a pre-vapor formulation in an electronic cigarette as taught by Karles because Sensabaugh and Karles are directed to nicotine compositions, and Karles demonstrates that a nicotine composition comprising volatiles from natural tobacco heated between 100 degrees Celsius and 160 degrees Celsius is suitable for use as a pre-vapor formulation in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054]).
Further, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide the nicotine composition as a gel because Sensabaugh, Karles, and Dayioglu are directed to nicotine compositions, Karles demonstrates that the composition may be used in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054] as applied above), and Dayioglu demonstrates that if the composition is a gel, the composition is less likely to leak from an electronic cigarette than a liquid composition (Dayioglu, [0044]).
Further, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide a cartridge comprising the nicotine composition of claim 16 because Sensabaugh, Karles, and Dayioglu are both directed to nicotine compositions, Karles demonstrates that the composition may be used in an electronic cigarette (Karles, [0032]-[0034], [0046]-[0051], [0054] as applied above), and Dayioglu demonstrates that an electronic cigarette can comprise a cartridge comprising a nicotine composition ([0002], [0005], [0102], [0110]; It is reasonably understood that the aerosol generating device having control electronics coupled to a heating element for heating an e-liquid is an electronic cigarette).
Conclusion
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/J.M.M./
Examiner, Art Unit 1755/PHILIP Y LOUIE/Supervisory Patent Examiner, Art Unit 1755