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 .
DETAILED ACTION
Claims 16-35 of C. Breffa et al., US 18/573,548 (May 30, 2022) are pending. Claims 22-30, 32 and 34-35 are withdrawn from further consideration by the examiner, as being drawn to the non-elected inventions of Groups (II)-(IV). Claims 16-21, 31 and 33 are under examination on the merits and are rejected.
Restriction
Restriction is required under 35 U.S.C. 121 and 372. This application contains the following inventions or groups of inventions which are not so linked as to form a single general inventive concept under PCT Rule 13.1. In accordance with 37 CFR 1.499, applicant is required, in reply to this action, to elect a single invention to which the claims must be restricted.
Group (I) Claims 16-21, 31 and 33 drawn to compound of Formula (I) . . . the compound of Formula (I) has at least 50 wt-% bio-based carbon content, relative to the total mass of carbon in the compound;
Group (II) Claims 22-28, 32 and 34-35 drawn to a compound of Formula (II) . . . the compound of Formula (II) has at least 50 wt-% bio-based carbon content, relative to the total mass of carbon in the compound.
Group (III) Claim 29 drawn to a process for preparing a compound of Formula (I);
Group (IV) Claim 30 drawn to a process for preparing a compound of Formula (II);
Applicant’s Election by Telephone
During a telephone conversation with Natali Richter on June 17, 2026 a provisional election was made without traverse to prosecute the invention of Group (I), 16-21, 31 and 33. Claims 22-30, 32 and 34-35 are withdrawn from further consideration by the examiner, as being drawn to the non-elected inventions of Groups (II)-(IV). 37 CFR 1.142(b). Affirmation of this election must be made by applicant in replying to this Office action.
Lack of Unity of Invention
The groups of inventions listed above do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features for the following reasons.
According to PCT Rule 13.2, unity of invention exists only when there is a shared same or corresponding special technical feature among the claimed inventions. The “Instructions Concerning Unity of Invention” (MPEP, Administrative Instructions Under the PCT, Annex B, Part 1(b)) state, “The expression 'special technical features' is defined in Rule 13.2 as meaning those technical features that define a contribution which each of the inventions, considered as a whole, makes over the prior art.” Thus, unity of invention exists only when the shared same or corresponding technical feature is a contribution over the art. The technical feature that unites the groups is not a contribution over the art.
Unity of Invention Is Lacking among Groups (I)-(IV)
In the instant case, Groups (I) and (III) lack unity of invention because even though the inventions of these groups require the common technical feature of a compound of Formula (I) this common technical feature is not special technical feature because it does not make a contribution over the art as set forth in the § 103 rejection below.
Groups (I) and (II) as well as Groups (I) and (IV) lack unity of invention because the groups do not share the same or corresponding technical feature. That is, Group (I) is directed to the compound of Formula (I), whereas Groups (II) and (IV) are directed to a compound of Formula (II).
Rejoinder
The examiner has required restriction between product or apparatus claims and process claims. Where applicant elects claims directed to the product/apparatus, and all product/apparatus claims are subsequently found allowable, withdrawn process claims that include all the limitations of the allowable product/apparatus claims should be considered for rejoinder. All claims directed to a nonelected process invention must include all the limitations of an allowable product/apparatus claim for that process invention to be rejoined.
In the event of rejoinder, the requirement for restriction between the product/apparatus claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product/apparatus are found allowable, an otherwise proper restriction requirement between product/apparatus claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product/apparatus claim will not be rejoined. See MPEP § 821.04. Additionally, in order for rejoinder to occur, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product/apparatus claims. Failure to do so may result in no rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01.
Claim Interpretation
During examination, a claim must be given its broadest reasonable interpretation consistent with the specification as it would be interpreted by one of ordinary skill in the art. MPEP § 2173.01(I); § 2111.01. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification.
Interpretation of the Claim 16 Term “bio-based carbon content”
Claim 16 requires “Formula (I) has at least 50 wt-% bio-based carbon content”.
16. A compound of Formula (I)
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,
Wherein
Q+ is a cation; and
the compound of Formula (I) has at least 50 wt-% bio-based carbon content, relative to the total mass of carbon in the compound.
The specification teaches that
In preferred embodiments, the bio-based carbon content as used herein is measured according to standard ASTM D6866-12, Method B.
. . .
Hence the term "bio-based carbon content" as used herein (if measured according to standard ASTM D6866-12, Method B) is defined by the equation: Bio-based carbon content= pMC* 0.95 (%)
Specification at page 2, line 10 through page 3, line 7 (emphasis added). Similarly, the art teaches that biobased content is calculated by ASTM D6866 as follows:
pMC = [Symbol font/0x44]14C/10 + 100(%)
biobased content = pMC [Symbol font/0xB4] 0.95%
M. Kunioka, 62 Radioisotopes, 901-925 (2013) (see page 904, col. 2). Where the term pMC (percent of modern carbon) means relative concentration of 14C to the NIST (National Institute of Standards and Technology) oxalic acid radio carbon standard reference material (SRM 4990). Kunioka at page 904, col. 2. %
Fossil fuels (and chemicals produced therefrom, such as ethylene), although derived living organisms, do not contain 14C. see e.g., C. Bettenhausen, Switching to sustainable surfactants, 100 Chem. Eng. News, 22-27 (2022). Presumably, this is because fossil fuels remain buried for millions of years where the 14C has fully radioactively decayed. Similarly, Haverly teaches that radiocarbon analysis distinguishes between biobased carbon and fossil carbon by measuring the ratio of 14C and 12C isotopes in a sample. M. Haverly et al., 237 Fuel, 1108-1111 (2019) (see page 1108, col. 1).
In view of the foregoing, the claim 16 term:
16 . . . has at least 50 wt-% bio-based carbon content, relative to the total mass of carbon in the compound.
is broadly and reasonably interpreted, consistently with the specification, as meaning that 50 percent by weight of the carbon atoms in a sample (in this case a Formula (I) sample) are derived from a modern source (e.g., a non-fossil fuel source) and therefore comprise 14C at levels commensurate with atmospheric carbon dioxide. The preferred specification embodiment cites ASTM D6866-12, Method B (specification at page 2, line 10), where the pMC, as calculated according to the following equation:
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must be greater than 50%. See ASTM Designation: D6866-12 (2021).
Claim Objections
Duplicate Claims
When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m). Applicant is advised that should base claim 1 be found allowable; its duplicate will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. MPEP § 608.01(m).
Dependent claims 20 and 21 are objected to as duplicative of each other. MPEP § 608.01(n)(III). Claims 20 and 21 are directed to the same compound of claim 16, where Q+ is sodium, i.e., sodium isethionate.
Rejections 35 U.S.C. 112(b)
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). A claim is indefinite when it contains words or phrases whose meaning is unclear. MPEP § 2173.05(e) (citing In re Packard, 751 F.3d 1307, 1314, 110 USPQ2d 1785, 1789 (Fed. Cir. 2014)).
Improper Preferences –Claim 19
Claim 19 is rejected under 35 U.S.C. 112(b) as being indefinite for recitation of exemplary claim language “preferably”. MPEP § 2173.05(d).
19. The compound of Formula (I) according to claim 16, wherein Q+ is selected from H+, NH4+, Li+, Na+, K+, 1/2Ca++,1/2 Mg++,1/2 Zn++, 1/3 Al+++, and combinations thereof, preferably wherein Q+ is Na+.
This claim 19 recitation of “preferably”, in this context, improperly provide for preferences and thereby renders confusion over the intended scope of claim 19. See, MPEP § 2173.05(d).
Claim Rejections - 35 USC § 103
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under AIA 35 U.S.C. 103(a) 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.
Claims 16-21 are rejected under 35 U.S.C. 103 as obvious over J. Day et al., US 5,384,421 (1995) in view of A. Morschbacker 49 Journal of Macromolecular Science, Part C: Polymer Reviews, 79-84 (2009) (“Morschbacker”); M. Zhang et al., 52 Industrial and Engineering Chemistry Research, 9505-9514 (2013) (“Zhang”) and T. Pu et al., 9 ACS Catalysis, 10727-10750 (2019) (“Pu”).
Claims 31 and 33 are rejected under 35 U.S.C. 103 as above in further view of T. Farrell et al., US 2002/0039977 (2002) (“Farrell”).
J. Day et al., US 5,384,421 (1995)
Day teaches that the preparation of esters of fatty acids with hydroxyalkylsulfonates, some of which are also known as isethionates and that these compounds are well known as valuable synthetic lime soap dispersants and detergents, wetting agents and materials which are particularly useful in the manufacture of toilet soaps. Day at col. 1, lines 5-12.
Day teaches fatty acid esters of sodium acylisethionate are prepared from sodium isethionate. Day at col. 2, lines 52-53. Day teaches that sodium isethionate (also called sodium hydroxyethane sulfonate) may be made by reacting ethylene oxide and sodium bisulfite. Day at col. 2, lines 59-61. The Examiner summarizes this reaction as follows:
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Day’s sodium isethionate meets the structural limitations of claim 16 Formula (I).
In Example 1, Day teaches a mixture of 9130 lb. sodium isethionate solution 52.4 % purity, total sodium isethionate is thus 4784.1 lb.), 25 lb. zinc oxide and 8250 lb. of coconut fatty acid.
Example 1
A 5000 gallon stainless steel stirred batch reactor equipped with a high performance agitator, a subsurface nitrogen purge line, and vacuum distillation piping with appropriately sized heat exchangers and vacuum receivers was charged with sodium hydroxyethane sulfonic acid solution (9130 pounds, 4150 kilograms) (Hostapon sodium isethionate solution from Hoechst Celanese Corporation, Somerville, N.J.) having 54 per cent solids and 52.4 percent purity (verified by High Pressure Chromatographic Analyses) and having a color rating of Color 5 (based on American Public Health Association (APHA) rating system described at page 199 of the Detergent Analysis Handbook cited above and incorporated by reference in its entirety herein); pulverized French Process zinc oxide (25 pounds, 11.36 kilograms) and coconut fatty acid (8250 pounds, 3750 kilograms).
Day at col. 8, lines 43-61. Thus, Day teaches a formulation comprising 37% sodium isethionate and 63% of further components. Day teaches that heating and processing the above mixture resulted in 24,000 pounds (10,909 kilograms) of a white pumpable fluid containing 36 weight percent sodium cocoylisethionate as the active ingredient. Day at col. 9, lines 43-46.
Note that the instant specification teaches that sodium cocoyl isethionate is a preferred compound of Formula (II). Specification at page 6, lines 25-30. The instant specification further teaches that, in a preferred embodiment, sodium isethionate is used as a precursor for the preparation of sodium lauroyl isethionate or sodium cocoyl isethionate. Specification at page 11, lines 5-10.
Difference between Day and Claim 16
Day does not teach the claim 16 limitation of:
16 . . . has at least 50 wt-% bio-based carbon content, relative to the total mass of carbon in the compound.
See Claim Interpretation above.
A. Morschbacker 49 Journal of Macromolecular Science, Part C: Polymer Reviews, 79-84 (2009) (“Morschbacker”)
Morschbacker teaches that bioethanol is raw material for chemical products. Morschbacker at pages 78-79. Morschbacker teaches that ethanol can be obtained by the fermentation of a sugar source, mainly sugarcane juice and molasses and hydrolyzed starch from corn grains. Morschbacker at page 79.
Morschbacker teaches that ethylene manufacture through ethanol dehydration is a process that has a low investment per ton of product, even in small scales. Morschbacker at page 84.
M. Zhang et al., 52 Industrial and Engineering Chemistry Research, 9505-9514 (2013) (“Zhang”)
Zhang teaches that compared with the process of petroleum to ethylene, ethanol dehydration to ethylene is economically feasible. Zhang at Abstract. Zhang reviews the development process and the current status of traditional ethanol catalytic dehydration to ethylene process, including research work on reaction mechanisms and efficient catalyst. Zhang at page 9505, col. 2. Zhang concludes that in the age of shortage of petroleum resources, biomass ethanol dehydration to ethylene is sure to become a very promising chemical process. Zhang at page 9511, col. 2.
T. Pu et al., 9 ACS Catalysis, 10727-10750 (2019) (“Pu”)
Pu teaches that industrially, ethylene oxide is currently produced by gas-phase selective ethylene oxidation (ethylene epoxidation) that is typically performed in fixed-bed tubular reactors with supported Ag/ Al2O3 catalysts at 230−270 °C and 1−3 MPa. Pu at page 10727, col. 1.
Obviousness Rationale
Claim 16 is obvious for the following reasons. One of ordinary skill informed by Day of the utility of sodium isethionate is motivated to prepare sodium isethionate by reacting ethylene oxide and sodium bisulfite as taught by Day. One of ordinary skill is further motivated to prepare the required ethylene oxide by gas-phase selective ethylene oxidation, which is taught by Pu to be the current industrial process. One of ordinary skill is motivated to prepare the required ethylene from bioethanol because Morschbacker and Zhang each teach that bioethanol is a convenient and advantageous feed stock. One of ordinary skill thereby arrives at sodium isethionate having 100% biobased carbon content. The sodium isethionate prepared as proposed above meets each and every limitation of claims 16-21, which are therefore obvious over the cited art.
The formulations of claims 31 and 33 are obvious as above in further view of T. Farrell et al., US 2002/0039977 (2002) (“Farrell”). Farrell teaches bar compositions comprising anionic surfactant, soap, free fatty acid and source of divalent cation sufficiently soluble to precipitate soluble soaps found in the molten process used to make the bars. Farrell at Abstract. Farrell teaches simple, unsubstituted sodium isethionate is particularly preferred as a mildness improver. Farrell at page 5. [0082]. Farrell teaches the following compositions comprising 3% sodium isethionate, that fall within the claim 31 and 33 ranges.
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Farrell at page 6, [095]. Claims 31 and 33 are obvious because one of ordinary skill is motivated to employ the above proposed sodium isethionate having 100% biobased carbon content in the above soap formulations of Farrell so as to arrive at the formulations of claims 31 and 33.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM.
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
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