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 .
This office action is in response to the amendment filed 6/24/2025. Claims 1, 3 are amended; claims 2 and 22 are cancelled; and claims 5-7, 12-17 and 19-20 are withdrawn from consideration as being drawn to non-elected invention. Accordingly, claims 1, and 3-21 are currently pending in the application.
Claim Rejections - 35 USC § 103
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.
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, 3, 8-11, 18 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Moravek et al (US 2019/0270892 A1).
Regarding claim 1, Moravek disclose a curable composition (i.e., reads on polymerizable composition in present claim 1) comprising methylene malonate represented by formula:
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(paragraph 0017) which reads on 2-methylene-1,3-dicarbonyl compound in present claim 1. See example 9, wherein the composition comprises diethyl methylene malonate and an ionic liquid (paragraph 0113). The activator can comprise an ionic liquid and examples of ionic liquid include a cation ionically associated with an anion. Examples of cations include C1-C32 tetraalkyl phosphonium cation (i.e., reads on quaternary phosphonium cation in present claim 1), C1-C32 tetraalkylammonium cation (i.e., reads on quaternary ammonium cation in present claim 1) and C1-C32 trialkylsulfonium cations (i.e., reads on tertiary cation in present claim 1). The anions can comprise a sulfonate, hexafluorophosphate and bis(trifluoromethylsulfonyl)imide (paragraph 0034) which read on the anion in present claim 1. Activator can comprise a base that is capable of initiating polymerization (paragraph 0031) which reads on polymerizable composition polymerizes when contacted with a polymerization initiator comprising at least one basic substance in present claim 1.
Moravek et al fail to disclose in a single embodiment as in present claims, an ionic compound which does not substantially react with compound (a).
However, Moravek et al in the general disclosure teach that activator can comprise an ionic liquid and examples of ionic liquid include a cation ionically associated with an anion (paragraph 0034). The activator includes latent precursor form of activator compounds that are capable of conversion from the latent precursor form into active form (paragraph 0030) which reads on ionic compound which does not substantially react with compound “a” in present claim 1. Therefore, in light of the teachings in general disclosure, of Moravek et al, it would have been obvious to one skilled in art prior to the filing of present application to include a latent precursor of the ionic compounds that are capable of conversion from the latent precursor form into active form, to prevent gelation, absent evidence to the contrary. Alternatively, examples of ionic compounds include C1-C32 tetraalkylammonium cation and anion such as hexafluorophosphate (paragraph 0034). Given that ionic liquid species, in Moravek et al, includes tetrabutylammonium hexafluorophosphate (i.e., C4-tetraalkyl ammonium cation) as in example 6, of present invention, one skilled in art prior to the filing of present application would have a reasonable basis to expect the ionic compound, of Movarek et al, to not substantially react with compound (a), absent evidence to the contrary.
Regarding claim 3, see example 9, wherein the curable composition comprises transesterification adduct of diethyl methylene malonate and 1,6-hexanediol (paragraph 0113). The transesterification adduct of methylene malonate and a diol is represented by formula:
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wherein X is a diol such as 1,6-hexanediol (paragraphs 0018-0019). It is noted that transesterification adduct of diethyl methylene malonate and 1,6-hexanediol has a molecular weight of about 370 g/mole.
Regarding claim 8, curable composition can be applied to side range of substrates including electronics (paragraph 0080).
Regarding claim 9, curable composition may be used in sealants and adhesives (paragraph 0008).
Regarding claim 10, once a curable composition is applied to a surface, the curing reaction can proceed to provide a cured composition (paragraph 0007).
Regarding claim 11, it is the Office’s position that it is the intended use of the cured product, of Moravek et al, in a semiconductor device.
Regarding claim 18, curable composition may be used in sealants and adhesives (paragraph 0008). once a curable composition is applied to a surface, the curing reaction can proceed to provide a cured composition (paragraph 0007).
Regarding claim 21, it is the Office’s position that it is the intended use of the cured product, of Moravek et al, in a semiconductor device.
Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Moravek et al (US 2019/0270892 A1) in view of Huang et al (Anionic polymerization of methylene malonate for high-performance coatings; Applied Polymer Materials; vol. 1, pp 657-663, 2019).
The discussion with respect to Moravek et al in paragraph 6 above is incorporated here by reference.
Moraveket al are silent with respect to water and its amount.
However, Moravek et al teach that suitable activators include base that is capable of initiating anionic polymerization of 1,1-diactivated vinyl compound (paragraph 0031). Additionally, Huang et al teach anionic polymerization of methylene malonate (title). DEMM (i.e., diethyl methylene malonate) incorporates two electronegative ester groups that facilitate the imbalance in electron distribution on the molecule. Negative charges tend to transfer and delocalize onto two ester groups, causing electropositivity of the vinyl group. Thus, vinyl group provides a site where anionic functional groups can easily attack to form an active center, enabling the anionic polymerization (page 659, col. 1, first full paragraph). Hydroxide ions in water could initiate DEMM and polymerize at a pH value of 4 or greater without adding any additional initiators. The conversion rate and the degree of polymerization strongly depended on the concentration of OH- in water. The polymerization of DEMM in water synergistically results from both by initiation by OH- and termination by proton. The OH- in water play the role of anionic initiator, while H+ acts as a terminator to stop the polymerization. At acidic conditions, termination plays a more dominant effect, higher pH values are associated with lower levels of H+, so the chain continues to propagate leading to high-MW polyDEMM. Initiation plays the dominant role when pH is higher than 7, thus MW begins to decrease with increasing pH value and OH- concentration. Thus, the polymerization of DEMM can be conducted using environmentally favorable conditions and it is significantly controlled by the pH value (page 659, bridging paragraph col. 1 to col. 2). Therefore, in light of the teachings in Huang et al and given that Moravek et al contemplate the polymerization of its composition by anionic polymerization, it would have been obvious to one skilled in art prior to the filing of present application, to include water, in the polymerizable composition, of Moravek et al, for above mentioned advantages. Additionally, it is the Office’s position that amount of water is a result-effective variable (MPEP 2144.5) since the amount used clearly affects the course of polymerization and the molecular weight of obtained polymer. Hence, the choice of a particular amount of water (such as the amount in present claims) is a matter of routine experimentation and would have been well within the skill level of, and thus obvious to, one of ordinary skill in the art.
Response to Arguments
It is noted that a request is sent to the application processing unit of USPTO to retrieve the foreign priority document. PTO-326 will be updated to reflect the submission of foreign priority document once it is added to the file wrapper.
The rejections under 35 U.S.C. 112(b), 102 and 103 as set forth in paragraphs 6, 9 and 12, of office action mailed 3/24/2025, are withdrawn in view of amendment and/or applicant argument and/or new grounds of rejection set forth in this office action, necessitated by amendment.
Conclusion
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KARUNA P REDDY whose telephone number is (571)272-6566. The examiner can normally be reached 8:30 AM to 5:00 PM M-F.
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/KARUNA P REDDY/Primary Examiner, Art Unit 1764