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 .
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 6, 11-12, and 15-18 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 6 recites “carbon” as one of the options for the R6 group. It is unclear what this is supposed to represent since the carbon would have to have additional substituents. The examiner recommends that “carbon” be amended to “methyl”.
In claims 11-12 it is unclear what the recited concentration is relative to. The examiner recommends that the claim be amended to specifically recite that the concentration is relative to the water-in-oil emulsion.
Claim 15 and its dependent claims recite a method “where the demulsifying compounds of claims 1, 5, and 6 are used alone or in combination”. However, claims 5 and 6 recite compounds which are a subset of those recited in claim 1, so it is not clear whether a compound meeting the limitations of claim 5 or 6 would also be considered a compound of claim 1. The examiner recommends that the claim be amended to recite that the method utilize a combination of demulsifier compounds (noting that “demulsifier compound” rather than “demulsifying compound” is consistent with the language used in claim 1).
In claim 16 it is unclear whether “including” means that the organic solvent is a mixture of all the recited solvents, or whether just one of the solvents is required. Applicant should clarify the claim by replacing “including” with either “comprising a mixture of” or “comprising at least one of”. For the purposes of examination, any of the recited solvent types are considered to meet the claim limitation.
In claim 18 “the demulsifying compounds are used at concentrations as low as 25 ppm” is indefinite since it is unclear whether applicant intends to recite a concentration range for the demulsifier compounds or whether applicant is requiring that compounds to be used in a concentration . If applicant intends to recite a concentration range, the examiner recommends that “are used at concentrations as low as 25 ppm” be amended to recite “are present in a concentration of at least 25 ppm, based on the total amount of the water-in-oil emulsion”
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 7 and 15 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 7 recites methyl as an option for the R6 group. However, claim 6, from which claim 7 depends, requires the R6 group to have 2 to 13 carbon atoms when it is an alkyl group. Applicant could overcome the rejection by amending “carbon” in claim 6 to “methyl”, as recommended in paragraph 3 above.
Claim 15 recites a method “where the demulsifying compounds of claims 1, 5, and 6 are used alone or in combination”. This fails to further limit the parent claims since “alone or in combination” covers all the possibilities. As stated in paragraph 3 above, the examiner recommends that the claim be amended to require a combination of demulsifier compounds.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 1-8 are rejected under 35 U.S.C. 102(a) as being anticipated by Sun (U.S. PG Pub. No. 2016/0348213).
In paragraph 35 Sun discloses tri-n-octyl quaternary ammonium naphthenic acid. The tri-n-octyl quaternary ammonium cation meets the limitations of the cation of claims 1-2 and 6 for the case where the R5 group is a methyl group and R1, R2, and R3 are octyl groups. Sun further discloses in paragraph 24 and formula (4) that naphthenic acid has a structure meeting the limitations of the anion of claims 1, 3-4, and 8 for the case where the R4 group has 12 to 15 carbon atoms and an aliphatic ring, namely a cyclopentane ring. The naphthenic acid of Sun further meets the limitations of the anion of claims 6-7, since the R5 group of the Sun, corresponding to the R6 group of the claim, can be a hydrogen or a methyl, and the value of p, corresponding to the value of n in the claim, is 6 to 8, within the claimed range. While Sun exemplifies a naphthenic acid formula containing a cyclopentane ring, naphthenic acid is a mixture cycloaliphatic ring-containing acids, including some cyclohexane ring-containing acids, leading to anions meeting the limitations of claim 5. Compounds containing formula (3) of Sun as the anion also meet the limitations of claims 1-3 for the case where R4 has 15 carbon atoms and comprises an aromatic ring. Claims 1-8 are therefore anticipated by Sun.
Claims 1-2 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ogihara (U.S. PG Pub. No. 2004/0219372).
In paragraph 51, Ogihara discloses numerous methyltrialkylammonium carboxylates, including octanoates and decanoates meeting the limitations of claims 1-2 for the case where R5 is a methyl group, R1, R2, and R3 are various alkyl groups, and R4 is linear alkyl having 7 or 9 carbon atoms. Claims 1-2 are therefore anticipated by Ogihara.
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 1-4 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang (CN 101050185 A).
An English-language machine translation of Zhang, which is attached, has been used in setting forth rejection, and the paragraph numbers referred to herein are those of the translation.
In paragraph 8 Zhang discloses ionic liquids using cycloalkanoic acid compounds as anions and quaternary ammonium bases as cations. In paragraph 9 Zhang discloses that the cycloalkanoic acids can be cycloheptylcarboxylic acid, 1-methyl-1-cyclohexanecarboxylic acid or 4-pentylcyclohexanecarboxylic acid, as well as various salicylic acid derivatives, which will all form anions in claims 1-3, and where the anions derived from the cyclohexanecarboxylic acid derivatives meet the limitations of the anion of claim 4. Zhang also discloses that trioctylmethylammonium hydroxide, which will lead to an ionic liquid having a trioctylmethylammonium cation, meeting the limitations of the cation of claim 1 where the R5 group is a methyl group and R1, R2, and R3 are octyl groups.
Zhang does not disclose specific ionic liquids meeting the limitations of claims 1-4. However, it would have been obvious to one of ordinary skill in the art to prepare the ionic liquids of Zhang to have the formulas recited in claims 1-4 since Zhang discloses that the ionic liquids can be derived from trioctylmethylammonium hydroxide and the cycloalkanoic acids discussed above.
Claims 1, 9-13, and 15-18 are rejected under 35 U.S.C. 103 as being unpatentable over Weers (U.S. PG Pub. No. 2020/0017776).
In paragraph 2 Weers discloses the use of ionic liquids as demulsifiers, and in paragraphs 44-45 discloses that preferred ionic liquids include those with a quaternary ammonium cation (R1R2R3R4N+) and a carboxylate anion. In paragraph 48 Weers discloses that the ammonium cation can be dicocodimethyl ammonium, ditallowdimethyl ammonium, or tributylmethyl ammonium, all of which meet the limitations of the cation of the compound of claim 1 where R5 is methyl. In paragraph 64 Weers discloses that the citrate can be oleate, linoleate, or stearate, meeting the limitations of the anion of claim 1 for the case where R4 has 17 carbon atoms.
In paragraph 80 Weers discloses using the ionic liquid to demulsify a water-in-oil emulsion, meeting the limitations of claim 9, as well as claim 15 for the case where the compound of claim 1 is used. In paragraph 87 Weers discloses that the ionic liquid is added in an amount of 1 to 5000 ppm of a fluid, encompassing the ranges recited in claims 11-12 and 18. In paragraph 77 Weers discloses that the ionic liquid can be contacted with a hydrocarbon-containing stream at a temperature of about 20° to 150° C, encompassing the range recited in claim 10. In paragraph 77 Weers discloses that the ionic liquids are particularly effective in disrupting emulsions in bitumen which can be formed by the addition of water to a hydrocarbon fluid during secondary oil recovery, meeting the limitations of the hot water bitumen process of claim 13. In paragraph 34 Weers discloses that the ionic liquids can be dissolved in water, various alcohols and hydrocarbons, and naphtha, as recited in claims 16-17.
The differences between Weers and the currently presented claims are:
i) Weers does not disclose a specific ionic liquid compound meeting the limitations of claim 1.
ii) Weers does not specifically disclose a water/alcohol solvent mixture. This relates to claim 17 only.
With respect to i), it would have been obvious to one of ordinary skill in the art to prepare the ionic liquids of Weers to have the formula recited in claim 1 since Weers, as discussed above, discloses that preferred cations and anions include quaternary ammonium cations and carboxylate anions meeting the limitations of claim 1.
With respect to ii), Weers discloses in paragraph 34 that suitable solvents include water and alcohols, and that alcohols are suitable as co-solvents. Case law holds that “It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art.” In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980) (citations omitted). It therefore would have been obvious to one of ordinary skill in the art to use a water/alcohol mixture as the solvent for the ionic liquid of Weers, meeting the limitations of claim 17.
In light of the above, claims 1, 9-13, and 15-18 are rendered obvious by Weers.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Farnand (U.S. Pat. No. 4,888,108) in view of Weers.
From column 8 line 45 through column 9 line 26, as well as Table 1, Farnand discloses a hot water bitumen process. The (S.B-D) solution obtained as the supernatant comprises 1.1% water, within the range recited in claim 14, and also about 3.3% water relative to the total amount of bitumen and water, also within the range recited in claim 14. Farnand indicates in the cited portion of Example 3 that emulsified water may be present and the use of a suitable demulsifier may include the settling rate of the solids in the material. Farnand does not disclose a specific suitable demulsifier.
The discussion of Weers in paragraph 15 above is incorporated here by reference. Weers discloses an ionic liquid meeting the limitations of the claimed demulsifier compound and useful in demulsifying emulsions formed from bitumen and water. The use of the ionic liquid demulsifier of Weers to demulsify the bitumen-containing composition of Farnand meets the limitations of claim 14.
It would have been obvious to one of ordinary skill in the art to use the ionic liquid demulsifier of Weers to demulsify the bitumen-containing composition of Farnand, since Weers teaches that the ionic liquids are useful in demulsifying emulsions formed from bitumen and water.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAMES C GOLOBOY whose telephone number is (571)272-2476. The examiner can normally be reached M-F, usually about 10:00-6:30.
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/JAMES C GOLOBOY/ Primary Examiner, Art Unit 1771
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