DETAILED ACTION
Table of Contents
I. Notice of Pre-AIA or AIA Status 3
II. Continued Examination Under 37 CFR 1.114 3
III. Claim Rejections - 35 USC § 103 3
A. Claims 1-4, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over US 2018/0155483 (“Kohl”) in view of 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 26 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over US 2016/0086829 (“Limary”) in view of Kohl and DiLauro. 11
IV. Response to Arguments 14
Conclusion 15
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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. Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant’s submission filed on 07/09/2026 has been entered.
III. 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 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 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. Claims 1-4, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over US 2018/0155483 (“Kohl”) in view of 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', R2", and R3 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-, provided that one of Z1 and Z2 is not -O-;
[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.
At the outset, the Instant Application (at ¶¶ 157-161 or equally ¶¶ 234-237 in US 2023/0295412, which is the pre-grant publication of the Instant Application) explicitly states that the SRPs disclosed in Kohl can be used in the instant invention, specifically replicating Formulas I and II of Kohl (Kohl: ¶¶ 101-102), reproduced below, as Formulas XIV and XV in the Instant Application.
With regard to claim 1, Kohl discloses,
1. (Currently Amended) A method comprising:
[1] depositing a stimulus responsive polymer (SRP) on a substrate [PWB, Package Exterior in Fig. 2, glass substrates in Fig. 17; ¶¶ 158, 163, 221],
[2a] wherein the SRP comprises a homopolymer [because the repeating unit is as shown in Formula I of Kohl, below, as stated in Kohl at ¶ 101], wherein the homopolymer comprises a structure of Formula (I):
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[i.e. Formula I
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168
288
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(¶ 101)]
[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', R2", and R3 is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl,
[3d] … [not taught] …
[3e] each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-, provided that one of Z1 and Z2 is not -O- [i.e. Z1 is -O- and Z2 is -CR2R3O-, one of R2 and R3 is H and the other is any of the indicated options listed in feature [3c] (Kohl: ¶ 101)];
[3f] r1 is an integer from 1 to 4; and
[3g] n is from about 3 to about 100,000 [i.e. 1 to 100,000 (Kohl: ¶ 101)], and
[4a] wherein the homopolymer [supra] comprises
[4b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [e.g. 17.4 kDa/mol to 103 kDa/mol (Kohl: Table 1, p. 19)] and
[4c] a ceiling temperature less than about 300°C [¶ 111, ¶ 186: “The temperatures were well below the ceiling temperature of PHA polymer [i.e. -40 ℃ as shown in Table 1 at p. 19] …”],
[5] thereby forming a film on a surface of the substrate [as shown in Figs. 2 and 17].
With regard to feature [1] of claim 1, Kohl states,
[0163] Also disclosed herein are various multilayered compositions or devices. In one example, a composition/device can comprise a plurality of layers wherein one layer comprises a copolymer as disclosed herein with a photo or thermocatalyst and the other layer comprise a substrate, e.g., metal, metal alloy, metal oxide, or graphitic oxide, or a non-degradable polymer.
(Kohl: ¶ 163; emphasis added)
With regard to features [3d] and [3f] of claim 1,
[3d] provided that at least one of R1, R2', and R2" is not H;
[3f] r1 is an integer from 1 to 4; and
Kohl does not teach feature [3d] of claim 1.
DiLauro, however, teaches that R1 is the halo group, -Cl, and r1 is 2, as follows. With regard to claim 1 DiLauro lacks only the limitation that “one of Z1 and Z2 is not -O-”, as follows:
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 (DiLauro: 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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164
302
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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
296
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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).
Finally, DiLauro teaches that including the chloro substituents stabilizes the polymer versus their absence (DiLauro: section entitled “Results and Discussion”).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to include the two, electron-withdrawing chloro substituents at the 4 and 5 positions of the phthalaldehyde in Formula I of Kohl, in order to improve the stability of the polymer as taught in DiLauro. As such, DiLauro may be seen as an improvement to Kohl in this aspect. (See MPEP 2143.)
The ceiling temperature would still be at least below room temperature, as evidenced by DiLauro which states that “[t]he increase in stability for PC12PA versus PPA does not prevent end-capped PC12PA from depolymerizing completely and continuously from end to end when exposed to a specific applied signal at room temperature” (DiLauro: p. 3255 section entitled, “Selective depolymerization of PC12PA”).
This is all of the limitations of claim 1.
With regard to claims 2-4, Kohl alone or modified according to DiLauro, as explained above, further discloses,
2. (Previously Presented) The method of claim 1, wherein said depositing comprises
[1] depositing a formulation comprising the SRP, and
[2] wherein the formulation comprises at least one of a solvent [Kohl: ¶¶ 153, 180, 225-226]], a plasticizer, an organic acid having a pKa more than or equal to 1, a photoacid generator [Kohl: ¶¶ 21, 22, 180, ], a thermal acid generator, and a dye [¶¶ 153, 225-226].
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 [supra].
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 [supra].
With regard to claim 18, Kohl modified according to DiLauro, as explained above, further discloses,
18. (Currently Amended) The method of claim 1,
[1] wherein the homopolymer comprises a structure of Formula (Ib):
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202
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[i.e. Formula II
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198
244
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(¶ 102)]
…
wherein:
[2a] each of R1, R5, and R6 is independently H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo [i.e. two of each of R1, R5, and R6 are -Cl, and two are H, as taught by DiLauro (supra)]
[2b] each of R2', R2", R3', R3", R4', and R4" is independently H, optionally substituted alkyl, or optionally substituted aryl [supra],
[2c] provided that at least one of R1, R2', and R2" is not H [i.e. -Cl, as taught by DiLauro (supra)];
[2d] 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 [supra],
[2e] provided that one of Z1 and Z2 is not -O- [i.e. Z2 is -CR2R3O-]
[2f] each of r1, r5, and r6 is, independently, an integer from 1 to 4 [each of r1, r5, and r6 is 2, as explained under feature [2a] ]; and
[2g] n1 is from 1 to 100 [i.e. 1-100,000 (¶ 102)].
With regard to feature [2g] of claim 18, the claimed range of 1 to 100 falls inside the range disclosed in Kohl of 1 to 100,000.
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.)
Here, there is no evidence of unexpected results given that there is no data or even one actual example compound/polymer of any of the claimed or disclosed formulas in the Instant Application.
For the same reasons as explained under claim 1, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to include the two, electron-withdrawing chloro substituents at the 4 and 5 positions of the phthalaldehyde in Formula II of Kohl, in order to improve the stability of the polymer as taught in DiLauro. As such, DiLauro may be seen as an improvement to Kohl in this aspect. (See MPEP 2143.)
B. Claims 26 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over US 2016/0086829 (“Limary”) in view of Kohl and 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', R2", and R3 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-, provided that one of Z1 and Z2 is not -O-;
[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 feature [3e] of claim 26, Limary does not disclose that the SRP does not have one of Z1 and Z2 not being -O-. With regard to features [3g] and [5a]-[5c], 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 (features [5a]-[5c]).
The monomer of the SRP of Limary is identical to that in DiLauro is very similar to that in Kohl and, as explained above in rejecting claim 1, the SRP of Kohl/DiLauro meets all of the limitations required of the SRP in claim 26 including the degree of polymerization, molecular weight, and ceiling temperature.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to use the SRP of Kohl/DiLauro as the SRP in Limary because it would be the substitution of one known SRP with a similar SRP suitable for the same purpose of functioning as a temporary coating that decomposes with an appropriate stimulus or trigger, as taught in each of Kohl and DiLauro. (See MPEP 2143.)
This is all of the limitations of claims 26 and 27.
IV. Response to Arguments
Applicant’s arguments filed 07/09/2026 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Conclusion
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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