DETAILED ACTION
Table of Contents
I. Notice of Pre-AIA or AIA Status 3
II. Claim Rejections - 35 USC § 112 3
A. Claims 1-4, 26, and 27 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. 3
III. Claim Rejections - 35 USC § 102 3
A. Claims 1, 3, and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by DiLauro, Anthony M., and Phillips, Scott T., “End-capped poly(4,5- dichlorophthalaldehyde): a stable self-immolative poly(aldehyde) for translating specific inputs into amplified outputs, both in solution and the solid state”, Polymer Chemistry, 2015, 6, pp. 3252-3258 (“DiLauro”). 4
B. Claims 1, 3, and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by the article to Lutz, J. Patrick entitled “Functionalized and Degradable Polyphthalaldehyde Derivatives”, J. Am. Chem. Soc., 2019, 141, pp. 14544-14548 8
IV. Claim Rejections - 35 USC § 103 11
A. Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Lutz in view of “Lists of cooling baths”, Wikipedia (available at https://en.wikipedia.org/wiki/List_of_cooling_baths). 11
B. Claims 1-3, 17, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over US 2019/0315961 (“Moore”). 12
C. Claims 26 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over US 2016/0086829 (“Limary”) in view of DiLauro. 17
V. Response to Arguments 20
VI. Pertinent Prior art 21
Conclusion 22
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I. 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 .
II. 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.
A. Claims 1-4, 26, and 27 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Each of independent claims 1 and 26 recites the limitation “R3” but fails to define what R3 may be. Claims 2-4, 26, and 27 are rejected for including the same indefinite limitation by depending from claim 1 or claim 26.
III. 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 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 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.
(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.
A. Claims 1, 3, and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by DiLauro, Anthony M., and Phillips, Scott T., “End-capped poly(4,5- dichlorophthalaldehyde): a stable self-immolative poly(aldehyde) for translating specific inputs into amplified outputs, both in solution and the solid state”, Polymer Chemistry, 2015, 6, pp. 3252-3258 (“DiLauro”).
Claim 1 reads,
1. (Currently Amended) A method comprising:
[1] depositing a stimulus responsive polymer (SRP) on a substrate,
[2a] wherein the SRP comprises a homopolymer, wherein the homopolymer comprises a structure of Formula (I):
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[2b] or a salt thereof,
[3a] wherein:
[3b] each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo and
[3c] each of R2, R2', and R2" is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl,
[3d] provided that at least one of R1, R2', and R2" is not H;
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-;
[3f] r1 is an integer from 1 to 4; and
[3g] n is from about 3 to about 100,000, and
[4a] wherein the homopolymer comprises
[4b] a molecular weight of from about 250 g/mol to about 1500 kg/mol and
[4c] a ceiling temperature less than about 300°C,
[5] thereby forming a film on a surface of the substrate.
With regard to features [1] and [5] of claim 1, inasmuch as there are no limitations on either the claimed “substrate” or “film”, the substrate may be taken to be, in the case of a solution film, the “glassware” in which the various end-capped poly(4,5-dichlorophthalaldehyde) polymers are synthesized (p. 3257, left col.) and in the case of a solid film, the sample holder in the thermogravimetric analysis instrument, TA Instruments, 2050 TGA (p. 3257, right col., 1st paragraph).
With regard to features [2a]-[4b] of claim 1, DiLauro discloses various end-capped poly(4,5-dichlorophthalaldehyde) polymers, e.g. polymers 9, 10, and 11 (reproduced below) in Fig. 4 on p. 3255:
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Mn = 14 kDaltons = 14 kg/mol
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128
310
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Mn = 30 kDaltons = 30 kg/mol
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126
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Mn = 24 kDaltons = 24 kg/mol
In each of polymers 9, 10, and 11, features [3a]-[3g] and [4b] are met as follows:
[3a] wherein:
[3b] each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo [specifically Cl] and
[3c] each of R2, R2', and R2" is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl,
[3d] provided that at least one of R1, R2', and R2" is not H;
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-;
[3f] r1 is an integer from 1 to 4 [specifically 2]; and
[3g] n is from about 3 to about 100,000 [as shown beneath each polymer above],
[4b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [as shown to the right of each polymer above].
In addition, each polymer is a homopolymers because only one monomer is used. It is well understood that end caps are not considered monomers and therefore do not make the polymer other than a homopolymers and Applicant has not acted as its own lexicographer to change the art-understood meaning of “homopolymer”. In fact, the Instant Application also includes end caps, i.e. “end groups”, but still calls the polymers homopolymers (e.g. ¶¶ 143, 242 of US 2023/0295412, which is the pre-grant publication of the Instant Application).
With regard to feature [4c] of claim 1, the ceiling temperature is below 236 ℃ for each of polymers 10 and 11, because the polymers entirely decompose below 236 ℃, as determined from the thermogravimetric analysis (Fig. 6, p. 3256), which is necessarily higher than the ceiling temperature.
This is all of the limitations of claim 1.
With regard to claim 3,
3. (Original) The method of claim 1, wherein the molecular weight of the homopolymer is a weight-average molecular weight of from about 500 g/mol to 1000 kg/mol.
It is held, absent evidence to the contrary, that, given the number-average molecular weights of polymers 9, 10, and 11, are in the range of 14 to 30 kg/mol, the weight-average molecular weights inherently necessarily falls within the claimed range from about 500 g/mol to 1000 kg/mol. As such, the burden of proof is shifted to Applicant to prove the contrary. (See MPEP 2112(I)-(V).)
Claim 17 reads,
17. (Currently Amended) The method of claim 1, wherein the homopolymer comprises a structure of Formula (Ia):
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or a salt thereof,
wherein:
each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo and
each of R2' and R2" is independently H, optionally substituted alkyl, or optionally substituted aryl,
provided that at least one of R1, R2', and R2" is not H;
r1 is an integer from 1 to 4; and
n is from 4 to 100,000; and
wherein the homopolymer comprises a linear polymer or a cyclic polymer.
Each of the linear homopolymers of DiLauro meet the requirements of claim 17, as explained under claim 1.
B. Claims 1, 3, and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by the article to Lutz, J. Patrick entitled “Functionalized and Degradable Polyphthalaldehyde Derivatives”, J. Am. Chem. Soc., 2019, 141, pp. 14544-14548
With regard to claim 1, Lutz discloses the several substituted polyphthalaldehydes (PPAs) in Table 1 (reproduced below from p. 14545), with the PPAs made from each of M1, M3, M4, and M8 meeting the requirements of Formula (I) and (Ia) of claims 1 and 17, respectively.
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428
380
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Given that the molecular weight of monomer M8, 3,4,5,6-tetrafluorophthalaldehye, is about 220 g/mol, it degree of polymerization, i.e. the claimed “n”, falling within the claimed range.
In addition, it is held, absent evidence to the contrary, that, given the number-average molecular weights of PPA formed from M8 of 16.2 kg/mol, the weight-average molecular weights inherently necessarily falls within the claimed range from about 500 g/mol to 1000 kg/mol, as required by claim 3. As such, the burden of proof is shifted to Applicant to prove the contrary. (See MPEP 2112(I)-(V).)
The experimentally determined ceiling temperatures for the PPAs, i.e. expt. Tc, made from the monomers M1 through M8 are shown in Table 2 (p. 14546) and are all below 300 ℃, as required by claims 1 and 17.
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370
482
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Thus at least the PPAs made from monomer M8 meets all of the requirements of claims 1 and 17. In addition, the PPAs made from monomers M4, 4-hexynylphthalaldehye, having a Tc of -23 ℃ meets the ceiling temperature requirements of claim 4, i.e. “less than about 30 ℃, or lower”.
Finally, inasmuch as there are no limitations on either the claimed “substrate” or “film”, the substrate may be taken to be, the substrate for the PPA M8 film is at least the sample support used in the differential scanning calorimeter used to determine the decomposition temperature (p. 14546, including Fig. 2).
This is all of the limitations of claims 1, 3, and 17.
IV. 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 of this title, 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.
A. Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Lutz in view of “Lists of cooling baths”, Wikipedia (available at https://en.wikipedia.org/wiki/List_of_cooling_baths).
Claim 4 reads,
4. (Original) The method of claim 1, wherein the ceiling temperature is less than about 60°C, less than about 50°C, less than about 40°C, less than about 30°C, or lower.
The prior art of Lutz, as explained above, teaches each of the features of claim 1.
While the PPAs made from monomers M1 and M3 meet the requirements of claimed Formula (I) and the ceiling temperature of “less than about 30°C, or lower” as required by claim 4, Lutz was unsuccessful at making the polymers because the dry ice bath of -78.5 ℃ is higher than the estimated ceiling temperatures, stating in this regard,
Propoxy-substituted M1, butylthio-substituted M2, and hexyl-substituted M3 all possess estimated ceiling temperatures <−78 °C and were therefore not expected to generate polymer under these conditions. Consistent with the predictions, these monomers failed to generate isolable polymers …
(Lutz: p. 14545, right col., 2nd full ¶)
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to make the suggested PPAs from at least monomers M1 and M3 using a temperature sufficiently low, that the polymers could be isolated, because Lutz at least suggests making such PPAs. There is a reasonable expectation of success because solvent/liquid nitrogen baths are well known that have temperatures below the predicted ceiling temperatures of the PPAs made from the monomers M1 (-122 ℃) and M3 (-80 ℃) that allows temperature to be controlled at temperatures of -84 ℃ for ethyl acetate/liquid nitrogen down to -160 ℃ for isopentane/liquid nitrogen. See the “List of cooling baths” which lists 19 different solvent/liquid nitrogen compositions having temperatures in this range.
Finally, Lutz did not give a molecular weight or degree of polymerization for the PPAs made from monomers M1 through M3 because they were not made (supra). However, given the molecular weight of a single molecule of M1, i.e. 4,5,-di-propoxylphalaldehyde is about 205 g/mol and M3, i.e. 4,5-di-n-hexylphalaldehyde is about 318 g/mol. Therefore, even a dimer meets minimum claimed molecular weight requirement.
In addition, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to make a PPA from monomer M1 or M3 having a molecular weight in the range of the other PPAs because these molecular weight are suitable for PPAs, as taught in Lutz. So done, the molecular weight and degree of polymerization would fall within the claimed ranges.
This is all of the limitations of claim 4.
B. Claims 1-3, 17, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over US 2019/0315961 (“Moore”).
With regard to claim 1, Moore discloses,
1. (Currently Amended) A method comprising:
[1] depositing a stimulus responsive polymer (SRP) [i.e. cyclic poly(phthalaldehyde) or cPPA (Fig. 1)] on a substrate [by spin casting (¶¶ 65-67, 83-84, 135)],
[2] wherein the SRP comprises a homopolymer [i.e. cyclic poly(phthalaldehyde) or cPPA (Fig. 1)], wherein the homopolymer comprises a structure of Formula (I):
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[2b] or a salt thereof,
[3a] wherein:
[3b] each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo [infra] and
[3c] each of R2, R2', and R2" is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl [infra],
[3d] provided that at least one of R1, R2', and R2" is not H [infra];
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3- [infra];
[3f] r1 is an integer from 1 to 4 [infra]; and
[3g] n is from about 3 to about 100,000 [infra], and
[4a] wherein the homopolymer comprises
[4b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [e.g. 231 kDa and 266 kDa (¶¶ 92-94)] and
[4c] a ceiling temperature less than about 300°C [e.g. about 140 ℃ to about 187 ℃ (¶ 96), as shown in e.g. Fig. 3; also ¶¶ 70, 73],
[5] thereby forming a film [of cPPA] on a surface of the substrate [whatever substrate on which the cPPA was solvent casted, e.g. a PTFE-lined petri dish (¶¶ 83-86)].
With regard to features [3a]-[3g] and [4b] of claim 1, Moore states that the cyclic poly(phthalaldehyde) can be substitute or unsubstituted:
[0046] The cPPA may have a chemical structure as shown in formula (I), where n can be at least 1. In some aspects, n can be at least 3. In some aspects, n can be any integer ranging from 3 to 400. The cPPA may be substituted or unsubstituted. The number average molecular weight of the cPPA may range from about 10 kDa to about 350 kDa.
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[0047] Suitable substituents include, but are not limited to, halogen, —NO2, alkyl, —OH, —NH2, —CN, haloalkyl, alkoxy, aryl, heteroaryl, heterocyclyl [sic], and the like.
(Moore: ¶¶ 46-47; emphasis added)
Although formula (I) is not shown to have substituents other than H, Moore explicitly states that formula (I) may be substituted with, e.g. halogen, alkyl, alkoxy, and aryl groups (id.). In addition, because carbon can only have 4 bonds, the only locations for substitution in formula (I) of Moore, above, are the same locations designated R1, R2', and R2" in the claimed Formula (I)
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to make at least one of the equivalent locations of R1, R2', and R2" in the claimed Formula (I) on each phthalaldehyde unit in the cyclic poly(phthalaldehyde) formula (I) of Moore above, substituted with a halogen, alkyl, alkoxy, and/or aryl group because Moore explicitly suggests making this substitution.
This is all of the limitations of claim 1.
With regard to claims 2 and 3, Moore further discloses,
2. (Original) The method of claim 1, wherein said depositing comprises
[1] depositing a formulation comprising the SRP [i.e. cPPA], and
[2] wherein the formulation comprises a solvent, a plasticizer, an organic acid having a pKa more than or equal to 1, a photoacid generator, a thermal acid generator, and/or a dye [¶¶ 65, 66, 69, 84].
3. (Original) The method of claim 1, wherein the molecular weight of the homopolymer is a weight-average molecular weight of from about 500 g/mol to 1000 kg/mol [e.g. 231 kDa and 266 kDa (¶¶ 92-94) or 10 kDa to about 350 kDa (¶ 46, supra)].
Claim 17 reads,
17. (Currently Amended) The method of claim 1, wherein the homopolymer comprises a structure of Formula (Ia):
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or a salt thereof,
wherein:
each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo and
each of R2' and R2" is independently H, optionally substituted alkyl, or optionally substituted aryl,
provided that at least one of R1, R2', and R2" is not H;
r1 is an integer from 1 to 4; and
n is from 4 to 100,000; and
wherein the homopolymer comprises a linear polymer or a cyclic polymer.
See the discussion under claim 1, which addresses al of the features of claim 17.
Claim 18 reads,
18. (Currently Amended) The method of claim 1, wherein the homopolymer comprises a structure of Formula (Ib):
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202
264
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or a salt thereof,
wherein:
each of R1, R5, and R6 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo;
each of R2', R2", R3', R3", R4', and R4" is independently H, optionally substituted alkyl, or optionally substituted aryl,
provided that at least one of R1, R2', and R2" is not H;
each of Z1, Z2, Z3, Z4, Z5, and Z6 is independently -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-, in which each of R2 and R3 is, independently, H, optionally substituted alkyl, or optionally substituted aryl;
each of r1, r5, and r6 is, independently, an integer from 1 to 4; and n1 is from 1 to 100.
The cyclic poly(phthalaldehyde) of formula (I) discussed in paragraphs [0046]-[0047] of Moore, above teaches all of the features of claim 18 for the same reasons as explained under claim 1.
With regard to the limitation n1 is 4 to 100 formula (I), Moore states the “n can be any integer ranging from 3 to 400” (¶ 46). In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); MPEP 2144.05(I)). In such a situation, Applicant must show that the particular ranges are critical, generally by showing that the claimed range achieves unexpected results relative to the prior art range. See In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). (See MPEP 2144.05(III)(A); emphasis added.)
This is all of the limitations of claim 18.
C. Claims 26 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over US 2016/0086829 (“Limary”) in view of DiLauro.
Claim 26 reads,
26. (Currently Amended) A structure comprising:
[1] a semiconductor substrate having a top surface and a bottom surface; and
[2a] a layer of a stimulus responsive polymer (SRP) comprising a homopolymer, wherein the homopolymer comprises a structure of Formula (I):
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[2b] or a salt thereof,
[3a] wherein:
[3b] each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo and
[3c] each of R2, R2', and R2" is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl,
[3d] provided that at least one of R1, R2', and R2" is not H;
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-;
[3f] r1 is an integer from 1 to 4; and
[3g] n is from about 3 to about 100,000,
[4] wherein the layer is disposed on the top surface and/or the bottom surface of the semiconductor substrate, and
[5a] wherein the homopolymer comprises
[5b] a molecular weight of from about 250 g/mol to about 1500 kg/mol and
[5c] a ceiling temperature less than about 300°C.
With regard to claim 26, Limary discloses, generally in Fig. 2C,
26. (Currently Amended) A structure comprising:
[1] a semiconductor substrate 212 [¶¶ 1, 3, 4, 10, 46, 55-58; Figs. 2A-2E] having a top surface and a bottom surface; and
[2a] a layer 239 of a stimulus responsive polymer (SRP) comprising a homopolymer [¶ 46: “a solvent 239 including stimuli-responsive sacrificial bracing material may be used to displace the fluid 224 or the optional transition solvent 238 (if used)”],
wherein the homopolymer comprises a structure of Formula (I):
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i.e.
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212
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[¶ 52]
[2b] or a salt thereof,
[3a] wherein:
[3b] each R1 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo [i.e. Cl] and
[3c] each of R2, R2', and R2" is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl,
[3d] provided that at least one of R1, R2', and R2" is not H [i.e. again, Cl];
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-;
[3f] r1 is an integer from 1 to 4 [i.e. 2]; and
[3g] … [not taught] …
[4] wherein the layer 239 is disposed on the top surface and/or the bottom surface of the semiconductor substrate 212, and
[5a]-[5c] … [not taught] …
With regard to features [3g] and [5a]-[5c] of claim 26 and claim 27,
[3g] n is from about 3 to about 100,000,
[5a] wherein the homopolymer comprises
[5b] a molecular weight of from about 250 g/mol to about 1500 kg/mol and
[5c] a ceiling temperature less than about 300°C.
27. (Original) The structure of claim 26, wherein the molecular weight of the homopolymer is of from about 500 g/mol to 1000 kg/mol.
Limary does not give the degree of polymerization (i.e. feature [3g]) or the molecular weight or ceiling temperature of the poly(4,5-dichlorophthalaldehyde) polymer shown in Fig. 5B.
As explained above, DiLauro, like Limary teaches a stimulus responsive polymer having the same monomeric unit structure of 4,5-dichlorophthalaldehyde. As further explained above, DiLauro teaches examples, i.e. polymers 9, 10, and 11, having the n and molecular weight (MW) falling within the ranges claimed in features [3g] and [5b] of claim 26 and claim 27, as well as having the ceiling temperatures of at least polymers 10 and 11 below 235 ℃ (supra) as required by feature [5c] of claim 26.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to use at least the n and molecular weight of the poly(4,5-dichlorophthalaldehyde) polymer of Limary to be in the range taught in DiLauro because Limary is silent as to these values such that one having ordinary skill in the art would use known n and MW suitable for the same compound used in the same capacity as a stimulus responsive polymer that decomposes with heat, such as the n and MW taught in DiLauro. (See MPEP 2143.)
This is all of the limitations of claims 26 and 27.
V. Response to Arguments
Applicant’s amendment to claim 2 overcomes the rejection under 35 USC 112(b).
Applicant’s amendment to claims 1 and 26 overcomes the prior art rejection over Ogihara.
Applicant’s arguments filed 03/31/2026 have been considered but they are not persuasive. Applicant argues that Moore does not disclose claimed Formula (I), as currently amended. Examiner respectfully disagrees for the reasons explained in the rejection. Paragraphs [0046]-[0047] of Moore states that the cyclic poly(phthalaldehyde) of formula (I) can be substituted with halogen, alkyl, alkoxy, and aryl groups.
VI. Pertinent Prior art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Kaitz, Joshua A., et al., “Dynamic Covalent Macrocyclic Poly(phthalaldehyde)s: Scrambling Cyclic Homopolymer Mixtures Produces Multi-Block and Random Cyclic Copolymers”, Macromolecules, 2013, 46, pp. 8121-8128 (“Kaitz”)
Kaitz (p. 8122) discloses 4-bromo and 4-methyl substituted cyclic polyphthalaldehydes (cPPA) homopolymers as well as their molecular weights Mn and Mp in Table 1 that fall within the claimed range of 250 g/mol to 1500 kg/mol:
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364
496
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100
1032
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Ceiling temperatures are not given.
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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERIK KIELIN whose telephone number is (571)272-1693. The examiner can normally be reached Mon-Fri: 10:00 AM-7:00 PM.
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Signed,
/ERIK KIELIN/
Primary Examiner, Art Unit 2814
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