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.
Claim 1 and the claims dependent therefrom 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.
Claim 1 stipulates that the dynamic bonding units of a hydrophobic polymer featuring dynamic bonding units embedded therein are dispersed “periodically” across the backbone. The word “periodically” is not expressly defined in the instant Specification and, therefore, should be considered to take on a textbook/dictionary meaning. A dictionary attaches to this term multiple meanings however one of these, i.e. “at regularly occurring intervals”, seems to be most applicable in the context of the its present usage.
A favored permutation of the instant invention is one where the hydrophobic polymer is a polyurethane/urea derived from a hydrophobic macromer bearing amine- or hydroxyl terminal groups and a diisocyanate. Insofar as there are only these two reactants, the urethane moieties (dynamic bonding units) will occur at regular intervals dictated by the length/degree of polymerization of the macromer and the identity of the polyisocyanate. What is not so clear, though, is if this stated structural requirement of dynamic bonding units appearing periodically implies that chain-extending small molecule diols/diamines, or small molecules that can react with two equivalents of a hydroxyl/amine-bearing compound, may not be employed in the preparation of the polymer insofar as they would ruin the established periodicity of the urethane residues established by the repeated insertion of -macromer/diisocyanate/macromomer/diisocyanate-.
One possible exception would be if the prepolymer comprises a single equivalent of macromer flanked at both ends with the residue of a diisocyanate and is, in turn, reacted with a small molecule diol, as is the case in at least one of the references cited infra. In this instance, all of the dynamic bonding units would still be present in a regularly repeating pattern, if not at regular intervals. In any case, to the extent that one of ordinary skill would not be able to ascertain whether or not a polyurethane prepared in this manner would conform with Applicants’ intended definition of “periodically embedded”, the claims are indefinite.
Claim Interpretation
Applicant defines the invention as an “underwater adhesive” but, to the extent that the only required component is a hydrophobic polymer containing periodically embedded dynamic bonding units, the claims are tantamount to product/polymer claims. Further, the Examiner submits that the “underwater adhesive” is merely an expression of intended use (though it is appreciated that any prior art invention deemed to represent an anticipation/obstacle to patentability must be capable of functioning in the stated capacity).
Section 2112.02 provides direction as to how phrases such as this are to be treated: “If the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. Pitney Bowes, Inc. v. Hewlett-Packard Co., 182 F.3d 1298, 1305, 51 USPQ2d 1161, 1165 (Fed. Cir. 1999). See also Rowe v. Dror, 112 F.3d 473, 478, 42 USPQ2d 1550, 1553 (Fed. Cir. 1997) (“where a patentee defines a structurally complete invention in the claim body and uses the preamble only to state a purpose or intended use for the invention, the preamble is not a claim limitation”); Kropa v. Robie, 187 F.2d at 152, 88 USPQ2d at 480-81 (preamble is not a limitation where claim is directed to a product and the preamble merely recites a property inherent in an old product defined by the remainder of the claim).
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)(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 1-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by the article entitled “Siloxane-Urea Segmented Copolymers” authored by Yilgӧr et al. and published in Polymer Bulletin (1982) 8, 535-542 as evidenced by the article entitled “Silicone-urea Copolymer as a Basis for Self-organized Multiphase Materials” authored by Komarov et al. and published in Polymer (2018) 143, 200-211.
Yilgӧr teaches copolymers derived from α,ω-bis(aminopropyl) polydimethylsiloxane (claim 2) and MDI using macromers of varied number-average molecular weight from 1,000 to 3670 g/mol. The urea groups formed within the polymer anticipate the claimed dynamic bonding units recited in claims 1 and 4.
While the disclosure is not forthcoming as to the presence of a plurality of phases of which one is constituted by the dynamic bonding/urea units, the Examiner submits that this aspect would be inherently satisfied given that the prior art copolymers are, like favored permutations of the claimed copolymers, derived from non-polar, hydrophobic macromers and polyisocyanates that together furnish urea groups at regular intervals capable of engaging in hydrogen bonding interactions (same products/same properties and/or structure at the molecular level), which is one of the dynamic bonding types in claim 3. As confirmation, Applicant is directed to the teachings of Komarov where they describe the modeling of polyureas obtained from the same precursors. Komarov even cites to the aforementioned Yilgӧr disclosure in the first full paragraph in the right column on page 201. See also Figure 1. In the same passage, they state that, through DMA and SAXS studies, the hard segment (includes urea groups) represents a phase separated portion of the polymer. See also the abstract where it is indicated that the hydrogen bonding interactions in which the urea groups participate drives the separation into phases.
As before, while there is no mention of the use of these copolymers as underwater adhesives, they would certainly be capable of being used in this capacity and, anyway, as an indication of intended use, it is accorded little patentable weight.
As for claims 5 and 7, the prior art adhesive contains no covalent crosslinks and, therefore, is not a structural adhesive but, rather, would be pressure sensitive adhesive (PSA)-like. One of ordinary skill, and even the layperson, recognizes pressure sensitive adhesives as reusable.
As for claims 6 and 8, Figure 3 in Komarov visually depicts the hard segment phase dispersed within the polydiorganosiloxane continuous phase consistent with claim 8. This orientation of the phases will allow the prior art adhesive to be applied underwater.
Claims 1-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by the article entitled “Dual Dynamic Bonds Self-healing Polyurethane with Superior Mechanical Properties over a Wide Temperature Range” authored by Zhang et al. and published in European Polymer Journal (2022), 163, 110934.
Applicant is directed to Figure 1 where there is depicted a synthetic scheme for the initial preparation of a polyurethane prepolymer derived from a mixture of polybutadiene diol and isophorone isocyanate. Subsequently the prepolymer is reacted with bis(2-hydroxydisulfide) thereby introducing yet another source of dynamic bonding units. In a final stage, the intermediate is reacted with 2-amino-4-hydroxyl-6-methyl pyrimidine, which constitutes a third source of dynamic bonding units. See also the subject matter under the headings 2.1 Materials and 2.2 Preparation. Whereas the reference does not address the concept of the dynamic bonding units representing a distinct nanophase within the bulk polymer material, the Examiner contends that this aspect is inherently satisfied by the prior art polymer given that urethane- and UPy groups form polar domains featuring substantial hydrogen bonding interactions surrounded by/interspersed within the substantially non-polar, hydrophobic polybutadiene domains consistent with the description in claim 8. This arrangement of the domains will allow the prior art adhesive to be applied underwater.
As for claims 5 and 7, the prior art adhesive contains no covalent crosslinks and, therefore, is not a structural adhesive but, rather, would be pressure sensitive adhesive (PSA)-like. One of ordinary skill, and even the layperson, recognizes pressure sensitive adhesives as reusable.
Claims 1-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Re et al., EP 359272 as .
Re describes the formation of polyurethanes derived from polyoxyperfluoroalkylene polyol, diisocyanate compounds featuring aryl- or cycloaliphatic rings, and short-chain diols or diamines (abstract). See also page 2, lines 51-53 and page 3, lines 3-40 where suitable embodiments of the perfluoropolyether are summarized, page 4, lines 1-11 for suitable short-chain diols/diamines, and page 4, lines 12-19 for exemplary polyisocyanates.
It has been speculated above that the language of claim 1, and in particular “periodically embedded” serves to exclude small molecule, or short-chain diols and diamines, known widely in the art as chain extenders. The Applicant is being compelled via a 35 U.S.C. 112(b) rejection formulated supra to make the record clear as to their intent for this limitation but, even if the Examiner’s supposition proves correct, Re still represents a foundation for rejection because it teaches a prepolymer synthesis
where the perfluoropolyether polyol is preliminarily reacted with a diisocyanate and it is the prepolymer that is being equated with the claimed polymer/adhesive for the purpose of this rejection.
Kamarov, cited above in association with the rejection over Yilgӧr validates the expectation that the prepolymers disclosed by Re would inherently be inherently in possession of the multiphasic behavior with the hard segments comprised of urethane groups constituting a discontinuous phase within a perfluoropolyether continuous phase. Indeed, the left column of page 201, third paragraph beneath the heading 4. Summary and conclusions says that the aggregation of hard (urethane-containing) segments to yield a separate domain is quite usual.
The same rationale given for holding claims 5 to 8 unpatentable in the above rejections applies here as well.
CN 110591051 teaches urethane polymers derived from a combination [0016] of α,ω-bis(aminopropyl) PDMS, 4,4’-diaminodiphenyl disulfide, isophorone diisocyanate, terephthaldehyde, and tris(2-aminoethylamine) as being suitable for underwater adhesive applications [0002]. This reference is not clearly anticipatory of the claimed invention insofar as the intent of “periodically embedded” has yet to be resolved. The Examiner has presumed that this limitation connotes that chain extenders such as terephthaldehyde may not be used. Should Applicants’ response lend to a different interpretation, this document may possibly be regarded as another basis for rejection in a subsequent Office communication.
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 4, 2026
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765