DETAILED ACTION
Summary
This is a non-final office action for application 17/928,011. The amendment in the RCE dated 16 March 2026 is acknowledged.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office 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 Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 16 March 2026 has been entered.
Claims 1-4, 8, 11-13 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over TACHIBANA (WO-2018225742-A1).
The TACHIBANA (WO-2018225742-A1) reference is in the IDS dated 3 January 2023. Family member US-20200157255-A1, also in the IDS dated 3 January 2023, is used for translation and paragraph numbers.
Regarding Claim 1, TACHIBANA teaches a vinyl alcohol-based polymer (Abstract) having the following structure ([0057]):
PNG
media_image1.png
293
526
media_image1.png
Greyscale
where a is 50-99.95 mol%, b is 0.05-30 mol%, c is 0-10 mol% and d is 0.001-10 mol% ([0058]). The a-unit satisfies the requirement of a vinyl alcohol unit. TACHIBANA teaches that this structure is formed by copolymerizing a vinyl ester with an unsaturated monomer convertible to a lactone-ring unit, preferably a carboxylic acid derivative having an unsaturated double bond ([0072]-[0073]). TACHIBANA exemplifies methyl acrylate ([0107]). The c-unit in the structure above is a lactone. The 0-10 mol% taught above for the c-unit encompasses the 1-5 mol% recited by the claim. TACHIBANA exemplifies 5 mol% in its synthetic example ([0109]) which satisfies the claim. In the synthetic example, TACHIBANA teaches that its methyl acrylate converts with adjacent alcohol units to form lactone rings ([0072]-[0073]), it does not teach any residual methyl acrylate or acrylic acid units ([0109], structure A above), which suggests that the conversion of methyl acrylate to lactone in the initial synthetic example is 100%. In the inventive examples, TACHIBANA subsequently performs a modification on these lactone units ([0019]) to form the d-units above ([0057]), leaving a percentage of lactone c-units to the sum of c-units and d-units of 80%, 64%, 82%, 96%, 76% and 72% in Examples 1-6 (Table 1). Examples 1 and 3-6 satisfy the requirement that 70-99 mol% of the constituent unit derived from the unsaturated monomer forms a lactone ring structure.
TACHIBANA teaches that the viscosity-average polymerization degree of its vinyl-alcohol-based polymer is 100-5000, more preferably 200-4000 with a polymerization degree of 100 or more resulting in higher mechanical strength and a polymerization degree of 5000 or less allowing for easier industrial production ([0065]). This overlaps the requirement of a polymerization degree of 2000 or more that is recited by the claim. TACHIBANA does not exemplify a polymerization degree over 2000 or more, but it would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention to modify the examples of TACHIBANA and a polymerization degree within the 100-5000 that is taught in its specification and is also 2000 or more as is recited by the claim. It is well settled that where the prior art describes the components of a claimed compound or compositions in concentrations within or overlapping the claimed concentrations a prima facie case of obviousness is established. See In re Harris, 409 F.3d 1339, 1343, 74 USPQ2d 1951, 1953 (Fed. Cir 2005); In re Peterson, 315 F.3d 1325, 1329, 65 USPQ 2d 1379, 1382 (Fed. Cir. 1997); In re Woodruff, 919 F.2d 1575, 1578 16 USPQ2d 1934, 1936-37 (CCPA 1990); In re Malagari, 499 F.2d 1297, 1303, 182 USPQ 549, 553 (CCPA 1974). For more discussion see MPEP 2144.05-I.
Regarding Claim 2, modified TACHIBANA teaches the invention of Claim 1 where TACHIBANA teaches many preferable carboxylic acid derivatives having an unsaturated double bond for its unsaturated monomer including methyl acrylate and methyl methacrylate ([0073]). TACHIBANA exemplifies methyl acrylate ([0107]).
Regarding Claim 3, modified TACHIBANA teaches the invention of Claim 1 where TACHIBANA broadly teaches 50-99.95 mol% vinyl alcohol units and 0.05-30 mol% ([0058]) which corresponds to saponification rates of 50/(30+50) to 99.95/(99.95+0.05), or 62.5-99.95% which overlaps the requirement of 95 mol% or more. TACHIBANA exemplifies a saponification rate of 99% or more ([0109]).
Regarding Claim 4, modified TACHIBANA teaches the invention of Claim 1. The claim duplicates the 2000 lower bound on the polymerization degree and adds a 5000 upper bound. TACHIBANA’s teaching of 100-5000 for the polymerization degree ([0065]) has the same upper bound as what is recited by the claim.
Regarding Claim 8, modified TACHIBANA teaches the invention of Claim 1. The use of the copolymer of Claim 1 as an anti-dehydrating agent for a cement slurry is an intended use. Case law holds that a recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967) and In re Otto, 136 USPQ 458, 459 (CCPA 1963). Since JP’811 teaches the same vinyl alcohol copolymer as the current invention, it is presumed to be suitable for the intended use of an anti-dehydrating agent for a cement slurry.
Regarding Claims 11, modified TACHIBANA teaches the invention of Claim 1 where TACHIBANA teaches that the unsaturated monomer forms the lactone c-units which are then further modified to form the d-units ([0067]). TACHIBANA teaches in the examples a percentage of lactone c-units to the sum of c-units and d-units of 80%, 64%, 82%, 96%, 76% and 72% in Examples 1-6 (Table 1). Examples 1 and 3-6 satisfy the recited requirement that 70 mol% or more and 98 mol% or less of the constituent unit derived from the unsaturated monomer forms a lactone ring structure.
Regarding Claim 12, modified TACHIBANA teaches the invention of Claim 1. TACHIBANA measures its degree of polymerization using a viscosity-average method ([0065], [0109]) so the viscosity of a polyvinyl alcohol copolymer solution is generally considered to be a function of the degree of polymerization of the copolymer. Because TACHIBANA teaches the same copolymer of vinyl acetate, vinyl alcohol and lactone units with the same percentages of each units ([0057]) with the same degree of polymerization ([0065]) and teaches a relatively small amount of other repeating units ([0057]), then one would inherently expect the copolymers taught by TACHIBANA to have the same 4%-aqueous solution viscosity as the polymers in the instant invention and satisfy the requirement that the 4%-aqueous-solution viscosity is within the recited range of 17-130 mPa-s.
Regarding Claim 13, modified TACHIBANA teaches the invention of Claim 1 where the constituent units derived from the unsaturated monomer (A) represent the c-units and d-units above ([0057]-[0058]). TACHIBANA generally teaches c is 0-10 mol% and d is 0.001-10 mol% ([0058]), preferably 0.1-7 mol% for c ([0061]) and 0.3-5 mol% for d ([0062]) which corresponds to a total of 0.001-20 mol%, preferably 0.4-12 mol% which encompasses the 1.5-3 mol% recited by the claim. TACHIBANA exemplifies 5% ([0109], Table 1) which is outside the recited range but it would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention modify the examples of TACHIBANA and use amounts of c-units and d-units that are within the ranges taught in its specification that are also within the range recited by the claim.
Regarding Claim 21, modified TACHIBANA teaches the invention of Claim 1 where TACHIBANA teaches 0-10 wt% of c-units and 0.001-10 wt% of d-units. TACHIBANA teaches that its lactone c-units are formed from an unsaturated monomer (exemplified as methyl acrylate) reacting with adjacent alcohol units to form lactone rings ([0072]-[0073]), and that its d-units are formed from further reacting the lactone unit with an amine compound ([0019]) so both c-units and d-units are ultimately derived from the unsaturated monomer (A). The 0.001-20 wt% of c- and d-units encompasses the 1-2.6 mol% range recited by the claim. TACHIBANA does not exemplify an amount of units derived from its (A) component that is within the recited range, but it would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention to modify the examples of TACHIBANA and form a copolymer with constituent units within the range taught in its specification that are also within the range recited by the claim.
Claims 5 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over TACHIBANA (WO-2018225742-A1) in view of FUJIWARA (JP-H01193306-A).
Regarding Claim 5, modified TACHIBANA teaches the invention of Claim 1 above. TACHIBANA teaches that its vinyl alcohol-based polymer is made into a powder for the purpose of evaluating water solubility ([0102]) but is silent on the size of the powder. FUJIWARA, in an invention of a polyvinyl alcohol obtained by saponification of a polyvinyl ester-based polymer (p. 2, par. 2), teaches the creation of a powder (p. 7, par. 7) which is 16 mesh or less, preferably 60 mesh or less. FUJIWARA teaches that powder that is larger than 16 mesh takes time to dissolve which is not preferable (p. 7, par. 8). Note that mesh is inverse unit where larger mesh corresponds to finer particle sizes. A powder with 16 mesh satisfies the recited requirement of passing through a 7.5 mesh sieve. It would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention to modify the invention of TACHIBANA, if needed, with the teachings of FUJIWARA and create a powder with 16 mesh or less for the purpose of making the powder easier to dissolve.
Regarding Claim 7, modified TACHIBANA teaches the invention of Claim 1. TACHIBANA teaches a method for producing a modified PVA by from a copolymer of vinyl acetate ([0108]). TACHIBANA teaches performing the reaction in methanol, with an added solution of sodium hydroxide in methanol then adding a solution of sodium hydroxide to perform the saponification reaction resulting in precipitation of a particulate saponification product ([0108]). TACHIBANA does not describe that its saponification occurs in a slurry state. FUJIWARA, in an invention of a polyvinyl alcohol obtained by saponification of a polyvinyl ester-based polymer (p. 2, par. 2) in a methanol solution (p. 2, par. 4), teaches that its saponification reaction occurs in a slurry state. FUJIWARA teaches that slurry saponification allows for obtaining PVA with a high degree of polymerization without going through the process of removing water. FUJIWARA also teaches that slurry saponification is known as a method for obtaining finely powdered PVA polymer without the need for pulverization (p. 2, par. 6). It would be obvious to one of ordinary skill in the art to modify the method of TACHIBANA and perform the saponification method in a slurry state for the purpose obtaining a high degree of polymerization without going through the process of removing water and obtaining a finely powdered PVA polymer product.
Claim 14-15 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over TACHIBANA (WO-2018225742-A1) in view of MORAN (US-5850880-A).
Regarding Claim 14, Claim 14 recites an antidehydrating method for a cement slurry using an anti-dehydrating agent which has the same compositional limitations of Claim 8, written in independent form. Modified TACHIBANA teaches the invention of Claim 8 above and the arguments rejecting the limitations of Claim 8 are included here by reference.
TACHIBANA does not teach a method for its use of modified polyvinyl alcohol as a dehydrating agent. MORAN, in an invention of powdered and liquid fluid loss additives for use in cementing (Abstract), MORAN teaches a liquid fluid loss additive which is formed by dissolving the vinyl alcohol/vinyl acetate copolymer in water (Col 5: 8-15) with other additives in a liquid formulation (Table 2) which is then added to the cement mix (Col 5: 8-10, Claim 1) which satisfies the recited method steps of the claim. MORAN exemplifies 88% saponified PVA/PVAc with a MW of 190,000 which calculates to a degree of polymerization of 190000/(0.88*44 + 0.12*86) ≈ 3874 which satisfies Claims 1. The teachings of MORAN that use in cement slurry is a known end use of polyvinyl alcohol. TACHIBANA teaches use of its polyvinyl alcohol copolymer in slurries ([0094]), specifically in cases where solvents which cause its copolymer to swell ([0094]) and TACHIBANA teaches that its copolymer has high water solubility ([0103], Table 1). The combination of its use in slurries and high water solubility suggests that the modified vinyl alcohol copolymers of TACHIBANA would still be useful as the vinyl alcohol copolymers taught by MORAN.
Regarding Claim 15, modified TACHIBANA teaches the invention of Claim 14 where MORAN teaches the use of vinyl alcohol copolymers as an antidehydrating agent. MORAN teaches amounts that vinyl alcohol is the primary component of its liquid fluid loss additive comprising 20-200 parts by weight out of 21.1-500 total parts (Col 5: 10-18) which overlaps the required 50% by mass or more. MORAN exemplifies a liquid fluid loss additive that is 91.56 wt% water, 7.28 wt% PVA copolymer and 1.16 wt% other components which calculates to 7.28/(7.28+1.16) ≈ 86.3 wt% which satisfies the claim.
Regarding Claim 19, modified TACHIBANA teaches the invention of Claim 14 where MORAN teaches the use of vinyl alcohol copolymers as a dehydrating agent. MORAN that its fluid loss additive is contained in 2-20 wt% based on the cement solids in the slurry (Claim 1) where the fluid loss additive contains 1000 parts water, 20-200 parts of vinyl alcohol copolymer and 1.1-150 parts other components (Claim 1; Col 5: 10-18), so the non-water components calculate to 21.1/(1000+21.1) to 350/(1000+350) or 2.1-25.9 wt% of non-water components in the additive. This further calculates to 0.021*0.02 to 0.259*0.2 or 0.04-5.19 wt% which slightly broader than the recited range of 0.1-5 parts per 100 parts. MORAN exemplifies that its fluid loss additive is 91.56 wt% water (Table 2) which leaves 8.44 wt% for the remainder. MORAN teaches in Example test 3, 800 g cement, 53 g preferred liquid additive (Table 3) which itself is 91.56 wt% water (Table 2). This calculates to (8.44/100)*53/800 ≈ 0.56 wt% of the non-water part of the fluid-loss additive which is within the 0.1-5 parts per 100 parts cement that is recited by the claim.
Regarding Claim 20, modified TACHIBANA teaches the invention of Claim 14 where MORAN teaches the use of vinyl alcohol copolymers as a dehydrating agent. MORAN teaches that its fluid loss additive is from 2-20 parts per 100 parts cement (Claim 1) but MORAN teaches examples which add additional water. In slurry tests 3-4, MORAN teaches adding 251 g or 253 g water and 53 g of its fluid additive to 800 g of cement. This calculates to 38.0 and 38.25 parts of added liquid per 100 parts cement which is within the 30-60 parts per 100 that is recited by the claim.
Claim 14-16 and 19-20 is rejected under 35 U.S.C. 103 as being unpatentable over TACHIBANA (WO-2018225742-A1) in view of LUDWIG (US-2576955-A).
Regarding Claim 14, Claim 14 recites an antidehydrating method for a cement slurry using an anti-dehydrating agent which has the same compositional limitations of Claim 8, written in independent form. Modified TACHIBANA teaches the invention of Claim 8 above and the arguments rejecting the limitations of Claim 8 are included here by reference.
TACHIBANA does not teach a method for its use of modified polyvinyl alcohol as a dehydrating agent. LUDWIG, in an invention of a low-water-loss cement slurry (Title, Col 1:4-8) teaches cement slurries with good water retention by adding polyvinyl alcohol to the slurry (Col 2: 21-33). LUDWIG teaches vinyl alcohol copolymers formed from polymerizing vinyl acetate and levels of hydrolysis of between 50-99% (Col 4:20-33). LUDWIG exemplifies adding its polyvinyl alcohol as a dry powder but teaches that it is understood that it could also be added as water solution to the cement slurry (Col. 4:12-19). TACHIBANA teaches use of its polyvinyl alcohol copolymer in slurries ([0094]), specifically in cases where solvents which cause its copolymer to swell ([0094]) and TACHIBANA teaches that its copolymer has high water solubility ([0103], Table 1). The combination of its use in slurries and high water solubility suggests that the modified vinyl alcohol copolymers of TACHIBANA would still be useful as the vinyl alcohol copolymers taught by LUDWIG.
Regarding Claim 15, modified TACHIBANA teaches the invention of Claim 14 where LUDWIG teaches the use of vinyl alcohol copolymers as a low-water-loss additive for cement. LUDWIG teaches other components for other purposes (retarders for delayed stiffening (Col 2: 18-20), foam stabilizers (Col 4: 71-73), but LUDWIG characterizes the vinyl alcohol copolymer as the water retention agent (Col 4: 34-38) so it can be interpreted that the vinyl alcohol copolymer is the water retention agent (i.e. ~100%) which would satisfy the requirement that the vinyl alcohol copolymer is 50% by mass or more.
Regarding Claim 16, modified TACHIBANA teaches the invention of Claim 14 where LUDWIG teaches the use of vinyl alcohol copolymers as a low-water-loss additive for cement. LUDWIG does not teach a dispersant.
Regarding Claim 19, modified TACHIBANA teaches the invention of Claim 14 where LUDWIG teaches the use of vinyl alcohol copolymers as a low-water-loss additive for cement. LUDWIG generally teaches that its vinyl alcohol copolymer is added in amounts of 0.025-5% by weight of the cement (Col 2: 24-26) which slightly encompasses the recited range of 0.1-5 pars per 100 parts cement. LUDWIG teaches a marked decrease in water loss when the vinyl alcohol copolymer is at least 0.1wt% or more (Col 5: 45-48). LUDWIG exemplifies in Examples 4-11, amounts of vinyl alcohol copolymer within the recited range (Table I).
Regarding Claim 20, modified TACHIBANA teaches the invention of Claim 14 where LUDWIG teaches the use of vinyl alcohol copolymers as a low-water-loss additive for cement. LUDWIG does not have a general teaching for the amount of the liquid formulation but LUDWIG exemplifies 60 parts water per 100 parts of Cement (Table I) which is on the endpoint of the 30-60 parts by weight per 100 parts by weight of the cement.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over TACHIBANA (WO-2018225742-A1) in view of LUDWIG (US-2576955-A) as applied to Claim 14 above, and further in view of HAYDON (US-20180230357-A1).
Regarding Claim 17, modified TACHIBANA teaches the invention of Claim 14 above where LUDWIG teaches the use of vinyl alcohol copolymers as a low-water-loss additive for cement. LUDWIG does not teach mixing further a polycarboxylate ether. HAYDON, in an invention of a cement activator composition which can be in a slurry state ([0060]) which can include a vinyl alcohol copolymer ([0092]) teaches that its composition can include an optional dispersant such as a polycarboxylate ether dispersant ([0076]). HAYDON exemplifies Liquiment polycarboxylate ether dispersants from BASF ([0076], [0110]). HAYDON teaches that dispersants help maintain desirable slurry rheology and can influence thickening time ([0076]). It would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention to further modify the invention of TACHIBANA and LUDWIG with the teachings of HAYDON and include a polycarboxylate ether dispersant for the purpose of maintaining a desirable slurry rheology and influencing the thickening time of the cement.
Allowable Subject Matter
Claim 6 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
The closest prior art, TACHIBANA (WO-2018225742-A1), cited in the rejections above, teaches a process for producing its vinyl alcohol copolymer which includes the recited copolymerization and saponification steps, but TACHIBANA teaches a washing step which includes methyl acetate and not a solution of a carboxylic acid in alcohol as is recited by Claim 6. JP’811 (JP-S49087811-A), cited in the previous office action, teaches a washing step using acetic acid, but the presence of an alcohol is only inferred as being present as the methanol byproduct of the saponification step, so JP’811 does not specifically teach a washing step with a solution of carboxylic acid in alcohol as is recited by Claim 6. One would not be motivated to combine the teachings of TACHIBANA and JP’811 to arrive at the claimed process.
Response to Arguments
Applicant's arguments filed 16 March 2026 have been fully considered but they are not persuasive.
The amendment cancels Claim 9. The warning that should Claim 9 be allowable that it would be objected to as being a substantial duplicate of Claim 14 is withdrawn.
Applicant argues that TACHIBANA teaches a synthetic example where 100% of its unsaturated monomer (A) (exemplified by methyl acrylate) are converted to lactone units, which is outside the range of 70-99 mol% that is recited by Claim 1 and Claim 14. In response, TACHIBANA teaches inventive examples where some of the lactone units in the composition of the synthetic example are further reacted with an amine compound to form d-units. These d-units have an acryl unit in the backbone of the chain, so these d-units are derived from the unsaturated monomer (A). TACHIBANA teaches in inventive examples 1 and 3-6 compositions where 3.6-4.8 mol% (Table 1) of the 5 mol% lactone in the composition of the synthetic example remains in the inventive composition. This calculates to a range of 76-96% of the units derived from the unsaturated monomer remaining as lactone units which is within the 70-99% range recited by the claim.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID R FOSS whose telephone number is (571)272-4821. The examiner can normally be reached Monday - Friday 8:00 - 5:00.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, ARRIE L REUTHER can be reached at (571)270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/D.R.F./Examiner, Art Unit 1764
/KREGG T BROOKS/Primary Examiner, Art Unit 1764