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 .
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 2 and 4 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 2 recites the broad recitation that “n” (defines the number of triads in the claimed resin) as up to 1000, and the claim also recites “n” being no more than 200 or 100, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
As for claim 4, the Examiner is unsure of Applicants’ intent when they say that the unsaturated polymer is a “mixture of” isotactic and syndiotactic 1,2-polybutadiene. Is the intent of the claim to disclose an actual mixture of polymers that are wholly isotactic and wholly syndiotactic, or does Applicant intend mean that that there is a single polymer with isotactic segments and syndiotactic segments?
Claim 4 is also indefinite because the molecular weight is not specified as one of a number-average molecular weight, a weight average molecular weight, or even possibly a viscosity average molecular weight.
Claim Interpretation
Claim 1 says of the claimed benzocyclobutene resin that is “has a” formula conforming with a subsequent structural representation. Based on the language employed, this certainly appears to constitute nothing more than a partial representation. Whereas the Examiner had initially had questions as to whether or not Applicant was suggesting with their structural representation that the polymer backbone was comprised entirely of units derived from 1,2-butadiene addition, it has since been surmised that the structure given is indeed not supposed to be extrapolated to the full structure of the resin. This construal is based on the fact that Applicant utilizes in their first couple of exemplifications of the invention a commercial polybutadiene (Nippon B-3000) that, according to its product data sheet has 10% 1,4-trans addition microstructure.
Claim Rejections - 35 USC § 102
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)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-9 and 11 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Chang et al., WO 2023/216980. Applicant is directed to Example 1 of this disclosure where an essentially identical synthetic production of a resin anticipatory of that claimed is summarized. See paragraph [0155] where 5.4 g Nippon B-3000, the same commercial butadiene used in a couple of Applicants’ own examples, is reacted with 9.1 g of benzocyclobutadiene such that their weight ratio is 0.59:1 consistent with the range of claim 5. An attached product catalog for Nippon polybutadiene products indicates that the number average molecular weight of B-3000 starting material is 3,200 g/mol. Given that the molecular weight of a single equivalent of butadiene is 54.09, there will be 3200/54.090 ≈ 59 repeat units, or about 20 triads and, therefore, the polymer conforms with the value of “n”.
The polymer is prepared in the presence of palladium acetate, tris(methylphenyl)phosphine, triethylamine, which fulfills the role of the “acid binding agent required by claims 3 and 7, with DMF (claim 8) as a solvent in a N2 environment. The reaction is carried out over a duration of 30 hours at 150° C thus satisfying claim 9.
As for claim 6, the molecular weight of bromobenzocyclobutene (Br-BCB) is 183.05 and thus there are added 9.1/183.05 = 0.05 mol of this compound. Example 1 indicates that 0.00015 mol of palladium acetate is used. From the formula
0.00015/0.05(x/100)
and isolating for x, it is determined that the percentage of catalyst used relative to halogenated benzocyclobutene is 0.3 mol%. The amount of tris(methylphenyl)phosphine is 4 times the amount of catalyst.
As for claim 4, the art is not forthcoming as to the tacticity of the suitable polybutadienes but, to the extent that it utilizes as a base polymer to be modified with bromobenzocyclobutene the same commercial product as is used in some of Applicants’ examples, it is reasonable to presume that the limitations of claim 4 are inherently satisfied.
Claims 1-3, 4-9, and 11 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Luo et al., U.S. Patent Application Publication No. 2024/0228765.
Applicant is directed to Example 1 of this disclosure where an essentially identical synthetic production of a resin anticipatory of that claimed is summarized. See paragraph [0155] where 100 g Nippon B-2000 is reacted with 169.44 g of benzocyclobutadiene such that their weight ratio is 0.59:1 consistent with the range of claim 5. An attached product catalog for Nippon polybutadiene products indicates that the number average molecular weight of B-2000 starting material is 2,100 g/mol. Given that the molecular weight of a single equivalent of butadiene is 54.09, there will be 2100/54.090 ≈ 39 repeat units, or about 13 triads and, therefore, the polymer conforms with the value of “n”.
The polymer is prepared in the presence of palladium acetate, tris(methylphenyl)phosphine, triethylamine, which fulfills the role of the “acid binding agent required by claims 3 and 7, with acetonitrile (claim 8) as a solvent in a N2 environment. The reaction is carried out over a duration of 24 hours at 85° C thus satisfying claim 9.
As for claim 6, the molecular weight of bromobenzocyclobutene (Br-BCB) is 183.05 and thus there are added 169.44/183.05 = 0.93 mol of this compound. Example 1 indicates that 7.48/224.15 = 0.033 mol of palladium acetate is used. From the formula
0.033/0.93(x/100)
and isolating for x, it is determined that the percentage of catalyst used relative to halogenated benzocyclobutene is 3.6 mol%. The amount of tris(methylphenyl)phosphine is 2.2 times the amount of catalyst.
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
Allowable Subject Matter
Claim 10 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 workup that follows benzocyclobutene modification of polybutadiene summarized in [0156-0158] includes all of the same operations as in claim 10 except for the acid wash and column chromatography. Whereas the former would be conceived of immediately by one of ordinary skill to neutralize residual triethylamine, it was not clear from the prior art why one of ordinary skill would have been motivated to utilize column chromatography in place of one or more steps of the process defined by WO ‘980. (U.S. ‘765 discloses a workup that resembles even less that which is claimed but it does contemplate passing the reaction mixture through a column of neutral alumina but this teaching doesn’t explain why a practitioner of the WO ’980 invention would have utilized this purification step in lieu of one or more of those already taught.)
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MARC S ZIMMER whose telephone number is (571)272-1096. The examiner can normally be reached M-F 8:30-5:00.
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March 7, 2026
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765