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 .
Response to Amendment
All outstanding rejections, except for those maintained below, are withdrawn in light of the applicant’s amendment filed on 8/25/2026
The new grounds of rejection set forth below are necessitated by applicant's amendment filed on 8/25/2026. In particular, claim 1 has been amended to include additional limitations that alter the scope of claim 1. Thus, the following action is properly made final.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action.
Claim Interpretation
Regarding claim 1, the amended limitation reciting “wherein the dental material contains no radically polymerizable monomers” is interpreted in light of the specification to mean a dental composition which contains no residual radically polymerizable monomers after curing rather than containing no radically polymerizable monomers whatsoever, which would stand in contradiction to the copolymer of claim 1 which is a combination of such monomers. This is based on instant specification page 2, line 32, where it says, “A disadvantage of known dental adhesives is that they usually have a more or less large residual monomer content after curing”.
Regarding claims 1, 4 and 5, both claims are directed toward dental compositions which comprise copolymers that are “obtainable” by the claimed process. Additionally, claim 7 is directed toward a dental material in which the mixture of copolymers AP and BP is obtainable by a process. These are product-by-process claims. MPEP 2113 says, “E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). Therefore, the claims are interpreted as directed to the products produced by the processes rather than the processes themselves.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over Sorenson (US 20190350677 A1) in view of Moszner (US 20170020791 A1) and further in view of Seib (US 4085264 A) and Wolter (US 20080187499 A1)
Regarding claims 1, 9 and 10, Sorenson discloses dental materials comprising adhesives which may comprise a copolymer formed from one or more monomers, and teaches the following suitable monomers:
MG: Methyl methacrylate (MMA) and butyl methacrylate (BMA);
MF: 2-hydroxyethyl methacrylate (HEMA);
MH: 10-methacryloyloxydecyl dihydrogen phosphate (MDP); and optionally,
MCS: Methacrylic acid.
(paragraphs [0019-0020]).
However, Sorenson does not teach a copolymer formed by reacting a copolymer with a radically polymerizable monomer MP in a polymer-analogous reaction which is neutralized with a base, nor does it teach a dental material containing no (residual) radically polymerizable monomers.
Moszner discloses dental compositions comprising oligomers which can be formed by copolymerizing monomers such as HEMA to improve solubility in water and alcohols, n-butyl methacrylate to improve solubility in acetone or ethyl acetate (paragraph [0024]), and strongly acidic monomers that preferably contain phosphonic acid monomers (paragraph [0015]). Moszner further teaches that polymerizable side groups can be inserted [into the copolymer] via a polymer-analogous reaction of HEMA with 2-isocyanatoethyl methacrylate (IEMA) (paragraph [0031]). However, Moszner does not teach acidic copolymers that are neutralized with a base, nor dental material containing no (residual) radically polymerizable monomers.
Seib discloses (meth)acrylic copolymers comprising monomers that contain acid groups that are neutralized after copolymerization using bases such as NaOH, KOH and triethylamine "to the extent of 50-80%" for the sake of optimum film formation (column 2, lines 53-62; claim 5). Seib is analogous to the instant application in that it pertains to copolymers formed from (meth)acrylic monomers. However, Seib does not disclose dental material containing no (residual) radically polymerizable monomers.
Wolter discloses dental composite compositions and teaches that residual monomers (which include radically polymerizable monomers) can cause an allergic reaction in the patient, so dental materials that are "free of monomers", meaning they contain no residual unreacted monomers after curing, are desirable (paragraphs [0002-0003]).
A person having ordinary skill in the art as of the effective filing date of the instant application would have found it obvious to apply the teachings from Moszner, Seib, and Wolter to the dental material of Sorenson as a combination of prior art elements using methods known in the art and the results would have been predictable.
Regarding claim 2, Moszner, as described above, teaches that HEMA and n-butyl acrylate are a result-effective variable in the solubility of the copolymer in various solvents. Although Moszner is silent on what amounts of these monomers would be appropriate to attain a given solubility property, it is well-established that the optimization of result-effective variables only requires ordinary skill in the art (see MPEP 2144.05, II). Therefore, a person having ordinary skill in the art would, through routine experimentation using methods known in the art, optimize the amounts of the monomers of the copolymer and would be expected to arrive at the respective amounts in the claimed ranges.
Regarding claim 3, Moszner discloses copolymerization of the monomers before reacting with IEMA occurring in an ethanol/water mixture (1/1; vol./vol.). Ethanol is an organic solvent. This mixture was then dialyzed in pure ethanol (paragraphs [0087-0088]). The claimed steps (IV) and (V) are optional.
Regarding claims 4 and 5, Moszner teaches dental compositions comprising at least one radically polymerizable oligomer (copolymer), which one would consider to be different in construction. In view of the references above, one of ordinary skill would find it obvious to produce copolymers that differ in that MG is methyl methacrylate in one and n-butyl methacrylate in another, thus producing different monomers analogous to AP and BP as claimed.
Regarding claim 6, the addition of monomer MCS would be obvious since Sorenson discloses methyl methacrylate as a comonomer, additionally, since monomer MCS is optional in all preceding claims on which claim 6 is dependent and claim 6 does not necessitate the presence of MCS, it is taken as inheriting the optionality from the preceding claims. Further, since Moszner teaches that monomers analogous to MG and MF are result-effective variables on copolymer solubility, a person having ordinary skill in the art would, through routine experimentation using methods known in the art, optimize the amounts of the monomers of the copolymer and would be expected to arrive at the respective amounts in the claimed ranges.
Regarding claim 7, since the copolymers analogous to AP and BP would be obvious to one of ordinary skill to produce and include in a dental composition as described above, and that the producing of these two monomers would necessitate separate solutions, their combination in a dental material would constitute as a “mixture” of the copolymers.
Regarding claim 8, Mosner describes the process of reacting the OH groups of the HEMA monomer in the terpolymer with IEMA which results in a copolymer comprising 61 mol.% HEMA monomer units and 30 mol.% IEMA monomer units. Since isocyanate groups react with the OH groups at a 1:1 ratio and HEMA has a single OH group and IEMA has a single isocyanate group, this would mean that 49% of the OH groups in the HEMA monomer units have reacted with the IEMA.
Regarding claim 11, as described above, Seib teaches that the acidic monomer is neutralized "to the extent of 50-80%", this is taken to mean that the amount of base added is such that it would neutralize 50-80 mol.% of the strongly acidic monomer MH.
Regarding claim 12, Moszner teaches that the oligomers (copolymers) have an average molecular weight particularly preferably between 10,000 and 100,000 g/mol (paragraph [0015]). The claimed range for the average molecular weight of the copolymers AP and BP in the composition is rendered prima facie obvious in view of the range disclosed in Moszner, which overlap with the claimed range. See MPEP 2144.05(I).
Regarding claim 13, Moszner discloses a dental composition that comprises particularly preferably 2-20 wt.% of the polymer (copolymer) and 0-70 wt.% of a solvent, preferably water (paragraphs [0060] and [0066]). The claimed ranges for the monomers in the composition are rendered prima facie obvious in view of the ranges disclosed in Moszner, which overlap with the claimed range. See MPEP 2144.05(I).
Regarding claims 14 and 15, Sorenson discloses dental materials comprising adhesives for intraoral and as an adhesive for dental restorations in non-therapeutic use (paragraphs [0008-0009] and [0042]).
Response to Arguments
Regarding the applicant’s remarks filed on 8/25/2026, the examiner responds as follows:
In the remarks section II. Moszner:
1. Applicant argues that Moszner does not teach the neutralization of the copolymer's acid groups, but that the composition of Moszner contains free acid groups.
The examiner agrees and notes that since claim 1 and 5 which claim a dental material comprising a copolymer which is "obtainable" by a process, these qualifies as product-by-process claims. This means that the product (being the copolymer) is the object of the claim and that an equivalent product found in the art as described in the claim is sufficient to read on the product, regardless of whether the claimed process is found in the art. The protected structure labeled as "step b terpolymer" in section 4 of the Office Action filed on (5/27/2026) contains a phosphonic acid group that is functionally neutralized via protection with methyl groups, however the examiner agrees that this is not equivalent to the Applicant's copolymer AP as neutralized with a base.
2. The applicant further argues that the examiner's interpretation of Moszner describing the phosphonic acid groups as "released" is not akin to neutralization.
The examiner agrees with the applicant and notes that the applicant’s further argument and supporting evidence clarifies what was disclosed in Moszner regarding how the phosphonic acid group of the terpolymer is "released".
3. Applicant argues that Moszner does not teach the copolymer AP of the instant amended claims but rather teaches away since the final terpolymer of Moszner contains free acid groups that are not neutralized.
The examiner agrees with regard to the applicant’s assessment of the final terpolymer of Moszner as containing free acid groups, however the examiner respectfully disagrees with the applicant’s assertion that Moszner definitively teaches away from neutralizing the terpolymer. There is no such teaching in Moszner that would exclude the possibility of any particular degree of neutralization of the terpolymer.
In the remarks section III. Shaof
1. The applicant argues that the application of Moszner in view of Shoaf to claim 11 is incorrect since the McKenna reaction as described by the applicant is not a neutralization reaction that uses methanol as a base. This is the reaction in Moszner where methanol is used when "releasing" the phosphonic acid group as in paragraph [0032] of Moszner.
The examiner agrees with the applicant.
In the remarks section IV. Pizzi
1. The applicant argues that Moszner in view of Pizzi does not render claim 12 obvious because Pizzi does not disclose any concrete adhesives.
The examiner respectfully disagrees with the applicant that Pizzi would be required to teach specific adhesives for a proper rejection to be made. The rejection was made as an application of a teaching from Pizzi to the composition of Moszner, which is an expression of KSR rational D as described in MPEP 2143.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Pocket Dentistry (Dental Polymers) discloses that the average molecular weight of dental polymers is a result-effective variable on the materials properties such as rigidity and brittleness.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KOLTON JONES whose telephone number is (571)272-9802. The examiner can normally be reached Generally Monday-Friday 8:00 am - 5:00 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph Del Sole can be reached at (517)272-1130. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KOLTON JONES/Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763
