DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 5 July 2023, in the matter of Application No. 18/260,350. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-8 are pending.
Claims 1, 3-5, and 8 have been amended.
No claims have been cancelled.
Thus, claims 1-8 represent all claims currently under consideration.
Priority
Acknowledgment is made of Applicants’ claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in the present application filed 5 July 2023 and in parent Application No. PCT/JP2022/004742 filed on 7 February 2022. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Applicant claims foreign priority to Application No. JP2021-023669, filed on 17 February 2021.
Domestic Priority data as claimed by applicant:
This application is a 371 of PCT/JP2022/004742 (02/07/2022)
Foreign Applications:
JAPAN 2021-023669 (02/17/2021)
Information Disclosure Statement (IDS)
The information disclosure statements submitted on 5 July 2023, 6 November 2024, and 7 November 2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the Examiner.
Specification
The disclosure is objected to because of the following informalities:
In Table 1 (paragraph [0071]), “Transmittancce” should read “Transmittance”.
Appropriate correction is required.
Claim Objections
Claim 6 is objected to because of the following informalities:
In line 1, “…A monomer composition, comprising…” should read “…A monomer composition comprising…”
Claim 7 is objected to because of the following informalities:
In line 3, “…25ºC…” should read “…25 ºC…”
Appropriate correction is required.
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.
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.
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.
Claims 6 and 8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Moser et al. (US 2018/0044448 A1; IDS of 11-07-2024; hereinafter “Moser”).
Regarding claims 6 and 8, Moser teaches novel stress-reducing crosslinking oligomers that have application in dental materials such as restoratives, thin films, hardcoats, composites, adhesives, and other uses subject to stress reduction (Moser; Abstract; paragraph [0004]). The disclosure of Moser further provides a curable composition comprising the addition-fragmentation oligomers (AFOs) and one or more free-radically polymerizable monomers, the addition-fragmentation oligomer providing a reduction in stress of the resultant polymers (Moser; paragraphs [0011] and [0043]; claim 22).
Of particular note, Moser teaches the preparation of AFO-9, a polymerizable group-containing phosphoric acid of the following structure:
PNG
media_image1.png
243
675
media_image1.png
Greyscale
and a composition comprising AFO-9 and urethane dimethacrylate (UDMA) (Moser; paragraphs [0215] and [0317]-[0318]; Table 3). Thus, the teachings of Moser anticipate every limitation of instant claims 6 and 8.
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.
Claims 1 and 3-5 are rejected under 35 U.S.C. 103 as being unpatentable over Craig et al. (US 2008/0306168 A1; IDS of 11-07-2024; hereinafter “Craig”).
Regarding claim 1, Craig teaches polymerizable dental compositions that comprise an ethylenically unsaturated monomer and a phosphorylated monomer (Craig; Title; Abstract; claims 1 and 8-9). Of particular note, Craig teaches the preparation of 6-methacryloxyhexyl phosphate (MHP) from 6-hydroxyhexyl methacrylate and phosphorous pentoxide (Craig; paragraphs [0103]-[0104]). The skilled artisan would recognize 6-hydroxyhexyl methacrylate as a polymerizable group-containing alcohol compound and 6-methacryloxyhexyl phosphate as a polymerizable group-containing phosphoric acid compound, in a manner consistent with the instant claim.
Craig further teaches a composition comprising MHP and diurethane dimethacrylate (UDMA; CAS No. 41137-60-4) (Craig; paragraph [0102]; Table 1; Example 2).
Craig fails to teach a method wherein the polymerizable group-containing alcohol compound reacts with phosphorous pentoxide in the presence of a urethane compound, as recited in instant claim 1. Instead, Craig teaches a composition comprising a polymerizable group-containing phosphoric acid compound (i.e., MHP) and a urethane compound (i.e., UDMA), as detailed above, wherein the urethane compound is added to the monomer composition including a polymerizable group-containing phosphoric acid compound at a later step after the production step of the polymerizable group-containing phosphoric acid compound from the reaction of the polymerizable group-containing alcohol compound with phosphorous pentoxide. However, the difference between the MHP production method of Craig and the monomer composition of Craig with respect to the recited instantly claim method is merely a change in sequence of adding ingredients. MPEP § 2144.04(C) states that “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results”. Although the Applicant demonstrates in the present application an alleged special technical effect of improved composition transparency as measured by spectral transmittance with monomer compositions produced in the presence of a urethane compound as recited in instant claim 1 as compared to monomer compositions prepared in the absence of a urethane compound (Specification; page 18, paragraphs [0071]-[0072], Table 1, Examples 1-19 and Comparative Examples 1-6), the criticality of this method step is unclear because there are no comparative examples showing that the transmittance of a monomer composition comprising a polymerizable group-containing phosphoric acid compound and a urethane compound wherein the urethane compound is added after the method step of producing the polymerizable group-containing phosphoric acid compound (i.e., as taught by Craig) is significantly different than the spectral transmittance of Examples 1-19 in the present application.
Furthermore, the method of Craig synthesizes 6-methacryloxyhexyl phosphate (MHP) from 6-hydroxyhexyl methacrylate and phosphorous pentoxide in methylene chloride solvent, and after the reaction the solvent was removed under vacuum to afford MHP product (Craig; paragraphs [0103]-[0104]). Thus, the skilled artisan would consider substituting the methylene chloride solvent with UDMA such that the intended product MHP is already present with its co-monomer UDMA as indicated in the composition of Craig that comprises MHP and diurethane dimethacrylate (UDMA; CAS No. 41137-60-4) (Craig; paragraph [0102]; Table 1; Example 2), and this substitution would improve the efficiency of the process with a reasonable expectation of success by removing the solvent removal step. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results, as described in MPEP § 2143(I)(B).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Craig by substituting UDMA for the methylene chloride solvent in the method step of producing MHP from 6-hydroxyhexyl methacrylate and phosphorous pentoxide to arrive at the claimed method. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a process with improved efficiency that obviates a solvent removal step and obtains a composition comprising MHP and UDMA in a one-pot process.
Regarding claims 3-4 depending from claim 1, Craig teaches the preparation of 6-methacryloxyhexyl phosphate (MHP) from 6-hydroxyhexyl methacrylate and phosphorous pentoxide, as detailed above (Craig; paragraphs [0103]-[0104]). The skilled artisan would recognize 6-hydroxyhexyl methacrylate as a polymerizable group-containing alcohol compound consisting of a methacryloyl group in a manner consistent with instant claim 3 that is also represented by Formula (B-a) of instant claim 4 when R1B-a is a methyl group, X1B-a is a divalent (i.e., nB-a + 1) organic group having 6 carbon atoms, and nB-a is 1.
Regarding claim 5 depending from claim 1, Craig teaches a composition comprising 6-methacryloxyhexyl phosphate (MHP) and diurethane dimethacrylate (UDMA; CAS No. 41137-60-4), as detailed above (Craig; paragraph [0102]; Table 1; Example 2). In this composition, MHP is present in 8.8% by weight and UDMA is present in 7.5% by weight (Craig; paragraph [0107; Table 1). Since Craig teaches that MHP is synthesized from 6-hydroxyhexyl methacrylate and phosphorous pentoxide, as detailed above (Craig; paragraphs [0103]-[0104]), the skilled artisan would recognize that when performing the method of Craig in a manner consistent with the method of instant claim 1 to arrive at the composition of Craig in a one-pot sequence would require the use of 7.5% by weight of UDMA, phosphorous pentoxide, and about 6.2% by weight of 6-hydroxyhexyl methacrylate (calculated from the relative molecular weight difference of 6-hydroxyhexyl methacrylate and MHP; 186.25/265.22 x 8.8% = 6.2%). In this instance, the addition mass of the urethane compound (7.5%) with respect to a total addition mass of the urethane compound and the polymerizable group-containing alcohol compound (7.5% + 6.2%) is about 55% (i.e., 7.5 / (7.5 + 6.2) x 100%), and this value resides within the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over Craig et al. (US 2008/0306168 A1; IDS of 11-07-2024; hereinafter “Craig”), as evidenced by Polydorou et al. (J. Biomed. Mater. Res. B. Appl. Biomater. 2009, 91B, 1-4; hereinafter “Polydorou”).
Regarding claim 2 depending from claim 1, Craig teaches the use of diurethane dimethacrylate, as detailed above (UDMA; CAS No. 41137-60-4) (Craig; paragraph [0102]; Table 1; Example 2). Based on the UDMA CAS No. disclosed by Craig, the skilled artisan would recognize that UDMA has a molecular weight of 470.56 g/mol and the following structure, as evidenced by Polydorou (Polydorou; page 2, Table I):
PNG
media_image2.png
219
1281
media_image2.png
Greyscale
Thus, the UDMA used in the method of Craig comprises a urethane compound that has a molecular weight per urethane bond of 235.28 (i.e., 470.56 divided by 2 urethane bonds), and this value resides within the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Moser et al. (US 2018/0044448 A1; IDS of 11-07-2024; hereinafter “Moser”) as evidenced by Moore et al. (Oper. Dent. 2008, 33-4, 408-412; hereinafter “Moore”), and further in view of Deguchi et al. (US 6,121,381; hereinafter “Deguchi”) as evidenced by Mayerhöfer et al. (ChemPhysChem 2020, 21, 2029-2046; hereinafter “Mayerhöfer”).
Regarding claim 7 depending from claim 6, the teachings of Moser as detailed above are incorporated herein.
In addition, Moser teaches that the compositions are photopolymerizable, and curing is affected by exposing the composition to a radiation source, preferably a visible light source that emits radiation between 250 nm and 800 nm and photocured at room temperature (Moser; paragraphs [0236]-[0237] and [0306]). Moser further teaches that the curable dental compositions maintain sufficient properties such as depth of cure (DOC), and describes DOCs ranging from 3.07-3.52 mm for monomer compositions comprising 1-3 wt.% of AFO-9 and UDMA (Moser; paragraphs [0154]; Table 4). Finally, Moser teaches that when the addition of AFO exceeds an optimal amount, properties such as depth of cure may be insufficient (Moser; paragraph [0169]). One of ordinary skill in the art would recognize that the depth of cure properties of the compositions of Moser necessitate that the compositions transmit visible light, as evidenced by Moore, who teaches that the depth of cure of visible-light activated resin has been the subject of considerable laboratory research, and this property depends upon the amount of light transmitted through the material (Moore; page 409, Col. 1, paragraph 3 and Table 2).
Moser fails to explicitly teach wherein the monomer composition has a spectral transmission in a range from 400 nm to 800 nm of 40% or more under conditions of 25 ºC and an optical path length of 10 mm.
However, Deguchi teaches urethane (meth)acrylate curable compositions, obtained by reacting an isocyanate compound with a (meth)acrylate compound having a hydroxyl group, that can be applied to dental materials (Deguchi; claim 1; Col. 1, lines 5-19).
Deguchi further teaches that the measurement of transmittance (%) of compositions were made in the range of 380-780 nm with a 3 mm thickness sample size (Deguchi; Col. 10; lines 49-52). Of particular note, Comparative Example 17 of Deguchi describes a curable monomer composition comprising methylmethacrylate (MMA) and UDMA in a 80:20 ratio with a transmittance of 88.9% (Deguchi; Table 7, Comp. Ex. 17), and all of the monomer compositions taught by Deguchi possess transmittances in the range of 87.9%-91.2%, respectively. The spectral range and transmittance values of Deguchi overlap with the ranges recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Finally, the teachings of Deguchi describe a composition cured at room temperature, such that the skilled artisan could reasonably deduce that the transmittance values were obtained at 25 ºC, in a manner consistent with the instant claim (Deguchi; Example 72).
Although Deguchi does not explicitly teach the exact same composition of Moser, the monomer compositions of Deguchi and Moser both comprise UDMA and (meth)acrylate compounds, such that the skilled artisan would recognize that these compositions would possess similar physical properties. MPEP § 2144.09(I) states that “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities.”
Deguchi fails to explicitly teach an optical path length of 10 mm, and instead teaches transmittance measurements performed on samples with a 3 mm thickness (Deguchi; Col. 10; lines 49-52). However, the spectral transmittance of Comp. Ex. 17 of Deguchi (transmittance of 88.9% at 3 mm optical path length) can be converted to the corresponding spectral transmittance with an optical path length of 10 mm by use of the Beer Lambert equation, as evidenced by Mayerhöfer (Mayerhöfer; page 2031, equation (1); page 2034, equation (4)). The Beer-Lambert law states that absorbance (A) is directly proportional to the distance in the medium (d):
A = ε • c • d
where (ε) is the molar absorptivity coefficient, (c) is the concentration, and the relationship between absorbance (A) and transmittance (T, in decimal form) is logarithmic:
A = -log10(T) or T = 10-A
Using these equations, the transmittance of 88.9% at 3 mm optical path length taught by Comp. Ex. 17 of Deguchi can be first converted to absorbance:
A3mm = -log10(0.889) = 0.051
Then, the directly proportional relationship between A and d can be used to calculate the new absorbance (A) for the path length of 10 mm:
A10mm/A3mm = d10mm/d3mm
Therefore, A10mm = A3mm • (10 mm/3 mm) = (0.051) • (10/3) = 0.170
Next, A10mm can be converted back to transmittance and multiplied by 100 to obtain the percent:
T10mm = 10-A10mm = 10-(0.170) = 0.676 •100 = 67.6%
Thus, the transmittance of Comp. Ex. 17 of Deguchi (transmittance of 88.9% at 3 mm optical path length) corresponds to a transmittance of 67.6% at a 10 mm optical path length, and this value resides within the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
The prior art as taught by Moser, Moore, and Deguchi reside in the closely overlapping technical field of polymerizable monomer compositions for use as dental materials, and the evidentiary teachings of Moore and Mayerhöfer relate to the technical field of spectral transmittance. Therefore, this prior art is deemed analogous art, as described in MPEP § 2141.01(a). Furthermore, the cited prior art demonstrates that high spectral transmittance is a well-documented technical feature of polymerizable monomer compositions for use in dental materials, and that monomer compositions similar to that of Moser possess high spectral transmittance, as taught by Deguchi. Overall, these teachings represent motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art references to arrive at the claimed invention, as described in MPEP § 2143(I)(G). Finally, since Moser teaches that the AFO content can be modified to optimize properties such as depth of cure, a technical effect that depends on material transmittance as evidenced by Moore and detailed above, the skilled artisan could further arrive at the claimed invention with a reasonable expectation of success through means of routine experimentation that is non-inventive in nature. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.”
Therefore, it would it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have arrived at the claimed composition based on the teachings of Moser, Moore, Deguchi, and Mayerhöfer through means of routine experimentation that is non-inventive in nature. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a composition for dental materials that possess an optimal depth of cure, as described above.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed composition. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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, Scarlett Goon can be reached on 571-270-5241. 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./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692