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 .
Status of the Claims
Claims 1-5 and 7-21 are pending.
Claims 1, 13, 14, and 20 are amended.
Claim 6 is cancelled.
Response to Amendments
Applicant’s amendments filed 05 September 2025 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claims 1, 13, and 20 is sufficient to overcome the rejection of claims 1-5 and 7-21 under 35 U.S.C. 103 as being unpatentable over Jefferson Chemical Co. Inc. (GB1340977, hereinafter Jefferson) in view of Lindsay et al. (US3896057, hereinafter Lindsay) and/or in further view of Barnes et al. (US20140290953, hereinafter Barnes). Due to the amendment to claims 1, 13, and 20 the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments on pages 7-9 of the remarks filed on 05 September 2025, with respect to the rejections of claims 1-5 and 7-21 under 35 USC 103 have been fully considered and are persuasive. Therefore, the rejections have been withdrawn. The amendment to independent claims 1, 13, and 20 changing “consisting essentially of” to “consisting of” required further search and a new ground(s) of rejection is/are provided below.
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 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 1-5, 7-11, 13-19, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Stapersma et al. (EP0351928, hereinafter Stapersma) in view of Jefferson Chemical Co. Inc. (GB1340977, hereinafter Jefferson) and Lindsay et al. (US3896057, hereinafter Lindsay).
Stapersma teaches the claims 1-4, 7, 13, and 21 limitations of a method of sulfonating a mixture of internal olefins, such as a mixture of C₁₃₋₁₄ vinylidene internal olefins or only C₁₈ vinylidene internal olefins, see Abstract, Pg. 3, Ln. 46-Pg. 5, Ln, 11, having the structure of
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, where R1 and R2 are each independently hydrogen and R3 and R4 are each independently C6 to C24 alkyl, meeting:
The mixture consisting of a plurality of internal vinylidene olefins having the structure in instant application claim 1 and in instant application claim 13;
The olefins are exposed to SO3 in a falling film reactor at a mol ratio of sulphonating agent to internal olefin of 1:1 to 1.25:1 to form sulfonated internal vinylidene olefins, where beta-sultones are readily formed and delta-sultones are formed only to a minor extent, see Abstract, Pg. 3, Ln. 1-Pg. 4, Ln. 40, Table, meeting:
The exposing to a sulfonating reagent, reacting, and delta-sultones in instant application claim 1 and in instant application claim 13;
The sulfonated reagent SO3 in instant application claim 2;
Within the range of molar ratio in instant application claim 3;
The specific reactor in instant application claim 4;
The beta-sultone in instant application claim 7;
The neutralization/hydrolysis is carried out with a water soluble base, such as sodium hydroxide in water, where the neutralization of the reaction product from the falling film reactor is generally carried out with an excess of base as compared to SO3, see Pg. 3, Lns. 10-17, Pg. 4, Lns. 3-11, meeting:
The exposing to a hydroxide base in water in instant application claim 1 and in instant application claim 13; and,
The excess base and water in instant application claim 21.
Stapersma does not teach the specific structure in instant application claims 1 and 13; and,
The limitations of claims 5, 8-11, and 14-18.
Jefferson teaches a method comprising:
Exposing vinylidene olefins prepared by any conventional process, such as dimerization of an alpha olefin and tailoring the feed, to SO3, where all of the vinylidene olefins of Jefferson are internal vinylidene olefins, to form sulfonated internal vinylidene olefins, see Pg. 1, Lns. 33-66, Pg. 2, Lns. 28-123, especially the formula, Pg. 3, lines 1-32 and 66-127, Pgs. 5-8, specifically Examples VIII-X and XV, Tables I-IV,
The internal vinylidene olefins are characterized by the following formula:
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, such as 2-hexeyl-decene-1, where R1 is C7 linear alkyl, R2 is C5 linear alkyl, A1 and A2 are each individually CH2, see Pg. 2, Lns. 28-123, especially the formula, meeting the specific 2-hexeyl-decene-1 structure in instant application claim 1 and in instant application claim 13; and,
The sulfonated internal vinylidene olefins are exposed to an alkali hydroxide, such as sodium hydroxide, for neutralization reaction in an aqueous solution, see Pg. 3, Lns. 4-32 and 87-107.
Jefferson teaches an internal olefin is sulfonated which will produce an internal olefin bearing a terminal sulfonate group, see Pg. 2, Lns. 54-60, Pg. 5, Table I, Examples VIII and IX, meeting wherein at least a portion of the sulfonated reaction product comprises an internal olefin bearing a terminal sulfonate group in instant application claim 5 and in instant application claim 14.
Jefferson teaches the internal vinylidene olefins are prepared as conventional process, such as by dimerizing C6 to C10 alpha olefins, mixtures thereof, and the like through the use of a triethylaluminum activator/catalyst, see Pg. 2, Lns. 61-78, meeting:
Wherein the mixture is prepared by dimerizing an alpha olefin or a second mixture thereof in instant application claim 9;
Wherein the alpha olefin is a C6 to C12 alpha olefin or a third mixture thereof in instant application claim 10; and,
Wherein the alpha olefin is dimerized by exposing the alpha olefin to a dimerization catalyst in instant application claim 11.
Jefferson teaches the sulfonated internal olefin is dissolved in water to create a highly-concentrated aqueous slurry with low viscosity that is easily pumped and poured, see Pg. 2, Lns. 4-24 and Pg. 4, Lns. 1-8, thus aggregates/micelles are not formed, meeting:
Further comprising: an aqueous fluid in which the sulfonated reaction product is dissolved in instant application claim 17; and,
Wherein the sulfonated reaction product is present in the aqueous fluid above a critical micelle concentration in instant application claim 18.
Jefferson teaches reacting an aqueous solution of alkali hydroxide in an excess of about 2 to 10 wt.% of the theoretical quality required in order to sufficiently neutralize the sulfonation product, sulfonic acids, sultones, and the SO3 sulfonating reagent, see Pg. 3, Lns. 9-25.
Lindsay relates to olefin mixtures of internal, component B, and vinylidene olefins, component C, that contain significant percentages of internal olefins and vinylidene olefins in addition to lower proportion of alpha/vinyl olefins, component A, see Col. 3, Lns. 15-38 and Col. 8, Lns. 10-65, composite mixtures or COS with 20 molecular percent alpha, and 80 molecular percent mixtures of internal vinylidene olefins, see Col. 1, Lns. 9-18 and Col. 3, Ln. 64-Col. 4, Ln. 3, are superior in detergency to similar well-known materials obtained from sulfonation of substantially pure straight chain alpha olefins, see Abstract.
Lindsay teaches distillation is used to control the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated, see Col. 6, Ln. 21-Col. 7, Ln. 17, meeting:
Distilling to create a mixture in instant application claim 1; and,
Wherein the first mixture is formed from distilling a second mixture in instant application claim 13.
Lindsay teaches sulfonating olefins with an SO3-N2 feed and NaOH neutralization to obtain a mixture of alkenyl sulfonic acid and hydroxy alkyl sulfonic acid, see Col. 15, Ln. 63-Col. 17, Ln. 7, Example 3, where the other preferred double-bond positional isomers of Type 1, i.e., the beta-gamma, gamma-delta, and delta-epsilon alkene sulfonates can be prepared by the thermal dehydration of hydroxy alkyl sulfonates, see Col. 12, Lns. 23-45, and the sulfurization of mixtures of alpha, internal, and vinylidene olefins leads to the misuse of the phase “consisting essentially of” because it is evident that double bonds in alkene disulfonic acids present in the sulfonation environment are in turn subject to further reaction to produce additional spectra, such as, trisulfonates of both the alkene and hydroxy alkyl varieties as well as similar tetrasulfonates and so forth, it is pointed out that most discussions do not dwell on such details and generally ignore the high order materials normalizing the monosulfonates (Types 1 and 2) to 100 percent frequently even without the bis-sulfonates/disulfonates (Type 3), various isomers result from the sulfonation of vinyl olefins, internal olefins and vinylidene olefins, the various spectra for these different types of olefins are generally similar, particularly in regard to the variety such as the percentages of the individual isomers, and the location of the internal double bonds and hydroxyl groups relative to the locations of the sulfonate group (SO3) linkages as determined by ring stability, and the like, for the ranges of components A, B and C in the raw material feed, see Col. 5, Ln. 40-Col. 6, Ln. 52, meeting:
Wherein at least a portion of the sulfonated reaction product comprises at least one hydroxylated compound bearing a terminal sulfonate group, a dehydration product thereof, or any combination thereof in instant application claim 15; and,
Wherein at least a portion of the sulfonated reaction product comprises a bis-sulfonate compound in instant application claim 8 and claim instant application 16.
Stapersma does not teach the limitations of claim 19.
With regard to the functional limitation pertaining to wherein the sulfonated reaction product has a lower critical micelle concentration in water than does a sulfonated reaction product formed from an internal olefin having a like number of carbon atoms. MPEP 2112.01 II. states “[p]roducts of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. Id.”
Stapersma, Jefferson, and Lindsay teach the sulfonated reaction product composition prepared by the claimed method, which is an identical or a substantially identical sulfonated reaction product composition; therefore, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). As a result, the sulfonated reaction product composition of Stapersma, Jefferson, and Lindsay will inherently possess the functional limitation of a lower critical micelle concentration in water than a sulfonated reaction product formed from an internal olefin having a like number of carbon atoms, meeting the limitations in instant application claim 19.
In addition, ““the discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer.” Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977).” See MPEP 2112 I.
Further, “[t]he normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges”, such as the critical micelle concentrations in water, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). See MPEP 2144.05.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the olefin sulfonating method of Stapersma by distilling the feed mixture to obtain the optimal olefin structure, as taught by Jefferson and Lindsay, of the feed mixture to produce the desired sulfonated compound, as taught by Jefferson and Lindsay, with a reasonable predictability of success for the purpose of controlling the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated to create a superior surfactant detergent rich with branched and internal structures exhibiting synergism, see Lindsay, Col. 1, Lns. 39-60 and Col. 6, Ln. 21-Col. 7, Ln. 17 and Jefferson, Pg. 1, Lns. 28-32.
By applying “routine optimization” and “predictable results” to select the optimal
concentration of internal vinylidene olefins to sulfonate, one of ordinary skill in the art would have been motivated to make these modifications because Jefferson and Lindsay provide a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a surfactant detergent by pursuing the known options within their technical grasp, such as controlling the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated, to create a superior surfactant detergent rich with branched and internal structures exhibiting synergism, see Lindsay, Col. 1, Lns. 39-60 and Col. 6, Ln. 21-Col. 7, Ln. 17, Jefferson, Pg. 1, Lns. 28-32, and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”. See MPEP 2141.
Selection of a known material, such as sulfonating internal vinylidene olefins, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as % internal vinylidene olefins in the feed mixture, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). See MPEP 2144.05.
Claims 12 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Stapersma et al. (EP0351928, hereinafter Stapersma) in view of Jefferson Chemical Co. Inc. (GB1340977, hereinafter Jefferson) and Lindsay et al. (US3896057, hereinafter Lindsay), as applied to claims 1-5, 7-11, 13-19, and 21 in the 35 USC 103 rejection above, in further view of Barnes et al. (US20140290953, hereinafter Barnes).
Stapersma teaches the claim 20 limitations of a method of sulfonating a mixture of internal olefins, such as a mixture of C₁₃₋₁₄ vinylidene internal olefins or only C₁₈ vinylidene internal olefins, see Abstract, Pg. 3, Ln. 46-Pg. 5, Ln, 11, having the structure of
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, where R1 and R2 are each independently hydrogen and R3 and R4 are each independently C6 to C24 alkyl, meeting:
The mixture consisting of a plurality of internal vinylidene olefins having the structure in instant application claim 20;
The olefins are exposed to SO3 in a falling film reactor at a mol ratio of sulphonating agent to internal olefin of 1:1 to 1.25:1 to form sulfonated internal vinylidene olefins, where beta-sultones are readily formed and delta-sultones are formed only to a minor extent, see Abstract, Pg. 3, Ln. 1-Pg. 4, Ln. 40, Table, meeting:
The exposing to a sulfonating reagent, reacting, and delta-sultones in instant application claim 20;
The neutralization/hydrolysis is carried out with a water soluble base, such as sodium hydroxide in water, where the neutralization of the reaction product from the falling film reactor is generally carried out with excess of base as compared to SO3, see Pg. 3, Lns. 10-17, Pg. 4, Lns. 3-11, meeting:
The exposing to a hydroxide base in water in instant application claim 20.
Stapersma does not teach the specific structure in instant application claim 20, distilling to form a second mixture, and dimerizing an alpha olefin in instant application claim 20; and, the metallocene catalysts of instant application claims 12 and 20.
Jefferson teaches a method comprising:
Exposing vinylidene olefins prepared by any conventional process, such as dimerization of an alpha olefin and tailoring the feed, to SO3, where all of the vinylidene olefins of Jefferson are internal vinylidene olefins, to form sulfonated internal vinylidene olefins, see Pg. 1, Lns. 33-66, Pg. 2, Lns. 28-123, especially the formula, Pg. 3, lines 1-32 and 66-127, Pgs. 5-8, specifically Examples VIII-X and XV, Tables I-IV,
The internal vinylidene olefins are characterized by the following formula:
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, such as 2-hexeyl-decene-1, where R1 is C7 linear alkyl, R2 is C5 linear alkyl, A1 and A2 are each individually CH2, see Pg. 2, Lns. 28-123, especially the formula, meeting the specific 2-hexeyl-decene-1 structure in instant application claim 20.
Jefferson teaches the internal vinylidene olefins are prepared as conventional process, such as by dimerizing C6 to C10 alpha olefins, mixtures thereof, and the like through the use of a triethylaluminum activator/catalyst, see Pg. 2, Lns. 61-78, meeting:
Wherein the mixture is prepared by dimerizing an alpha olefin or a third mixture thereof in instant application claim 20.
Lindsay teaches distillation is used to control the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated, see Col. 6, Ln. 54-Col. 7, Ln. 17, meeting distilling a first mixture to create a second mixture in instant application claim 20.
Barnes teaching the dimerization of an alpha olefin with a dimerization metallocene catalyst to create internal vinylidene surfactant olefins, such as 2-hexyl-1-decene, concentrated by distillation to remove unreacted monomer and any trimer or higher oligomers that may have formed, and the internal vinylidene is selected based on the physical properties of the resultant surfactant, see Paras. [0031]-[0038], meeting:
A dimerization catalyst comprising a metallocene in instant application claim 12 and in instant application claim 20; and,
Meeting distilling a first mixture to create a second mixture in instant application claim 20.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
Stapersma to obtain the olefin from the dimerization method with the metallocene catalyst and distillation teaching of Jefferson, Lindsay, and Barnes and to modify the olefin sulfonating method of Stapersma by distilling the feed mixture to obtain the optimal olefin structure of the feed mixture to produce the desired sulfonated compound, as taught by Lindsay, with a reasonable predictability of success for the purpose of producing a single purified internal vinylidene olefin in order to optimize the physical properties of the final sulfonated olefin, see Barnes, Paras. [0033];[0035];[0038], thus controlling the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated to create a superior surfactant detergent rich with branched and internal structures exhibiting synergism, see Lindsay, Col. 1, Lns. 39-60 and Col. 6, Ln. 21-Col. 7, Ln. 17.
By applying “routine optimization” and “predictable results” to select the optimal internal vinylidene olefins to sulfonate, one of ordinary skill in the art would have been motivated to make these modifications because Jefferson, Lindsay, and Barnes provide a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a surfactant detergent pursuing the known options within their technical grasp, such as controlling the physical properties of the final sulfonated olefin by dimerization of an alpha olefin using a metallocene catalyst to produce a single internal vinylidene olefin, see Barnes, Paras. [0033];[0035];[0038], thus controlling the type of olefin, the number of carbon atoms on each type of olefin, and the structure of each type of olefin to be sulfonated to create a superior surfactant detergent rich with branched and internal structures exhibiting synergism, see Lindsay, Col. 1, Lns. 39-60 and Col. 6, Ln. 21-Col. 7, Ln. 17 and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”. See MPEP 2141.
Selection of a known material, such as a metallocene dimerization catalyst, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as % internal vinylidene olefins in the feed mixture, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). See MPEP 2144.05.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/YO/Examiner, Art Unit 1692
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691