DETAILED ACTION
Table of Contents
I. Notice of Pre-AIA or AIA Status 3
II. Election/Restrictions 3
III. Information Disclosure Statement 3
IV. Claim Rejections - 35 USC § 112 3
A. Claim 2 is 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
V. Claim Rejections - 35 USC § 102 4
A. Claims 1-4, 16, and 17 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by US 2019/0315961 (“Moore”). 5
B. Claims 1-3, 26, and 27 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 2015/0221500 (“Ogihara”). 8
VI. Claim Rejections - 35 USC § 103 10
A. Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Moore. 10
VII. Pertinent Prior Art 11
Conclusion 12
[The rest of this page is intentionally left blank.]
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. Election/Restrictions
Applicant’s election without traverse of invention group I and species group defined by formula I(Ia, Ib), claims 1-4, 16-18, 26, and 27, in the reply filed on 10/30/2025 is acknowledged.
The claims drawn to the non-elected species may be entitled to rejoinder under the conditions explained in the Requirement for Election/Restriction at page 8.
III. Information Disclosure Statement
The foreign references cited in the IDSs filed on 04/21/2023 and 01/09/2025 have been considered to the extent that they have been provided in the English language. (See MPEP 609.04(a)(III) and 37 CFR 1.98(a)(3).)
IV. 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. Claim 2 is 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.
Claim 2 recites the limitation “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.” As such the claim may be reads as (1) only the dye being optional with each of the preceding listed components being required, or as (2) one or more of any of the listed components is required.
For the purposes of examination, the claim will be read as broadly as allowed by the claim language, i.e. that one or more of any of the listed components is required.
V. 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 1-4, 16, and 17 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by US 2019/0315961 (“Moore”).
With regard to claim 1, Moore discloses,
1. (Original) 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)], and
[3a] wherein the homopolymer comprises
[3b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [e.g. 231 kDa and 266 kDa (¶¶ 92-94)] and
[3c] 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],
[4] 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)].
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)].
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 [¶ 4].
Claims 16-17 read,
16. (Currently Amended) The method of claim 1, wherein the homopolymer comprises a structure of one of formulas (I)-(XIII):
PNG
media_image1.png
170
144
media_image1.png
Greyscale
or a salt thereof,
wherein:
each R is, independently, H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo;
each of R2, R2', R2", and R3 is, independently, H, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted aryl;
each of R4, R4', and R4" is, independently, H, optionally substituted alkyl, optionally substituted aminoalkyl, optionally substituted heteroalkyl, or R4', and R4", taken together with the nitrogen atom to which each are attached, form a heterocyclyl group, as defined herein;
Ar is optionally substituted aryl, optionally substituted alkyl, or optionally substituted aralkyl;
each of L1 and L2 is, independently, a covalent bond, optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted arylene, or optionally substituted cycloalkylene;
each of Z1 and Z2 is, independently, -O-, -S-, -CR2R3O-, -OCR2R3O-, -OCR2R3-, -CR2R3S-, -SCR2R3S-, or -SCR2R3-;
r1 is an integer from 1 to 4; and
n is from about 3 to about 100,000; and
wherein the homopolymer comprises a linear polymer or a cyclic polymer.
17. (Original) The method of claim 1, wherein the homopolymer comprises a structure of formula (Ia):
PNG
media_image2.png
164
150
media_image2.png
Greyscale
or a salt thereof,
wherein:
each R1 is, independently, H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted aryl, or halo;
each of R2' and R2" is, independently, H, optionally substituted alkyl, or optionally substituted aryl;
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.
Moore discloses cyclic cPPA formula (I) (reproduced below from page 3 of Moore).
PNG
media_image3.png
180
244
media_image3.png
Greyscale
Here, each of R1, R5, and R6 is H, each of R2', R2", R3', R3", R4', and R4" is H, each of Z1, Z2, Z3, Z4, Z5, and Z6 is -O-, each of r1, r5, and r6 is 1.
With regard to the limitations, n = 3 to 100,000 or n = 4 to 100,000 formula (I), Moore states,
[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.
(Moore: ¶ 46; emphasis added)
Given the molecular weight of a monomer of poly(phthalaldehyde) is about 134 Da, the examples of Mn of 231 kDa and 266 kDa, given n ≈ 1724 and 1985, respectively, which fall within the claimed range for n.
This is all of the features of claims 16 and 17.
B. Claims 1-3, 26, and 27 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 2015/0221500 (“Ogihara”).
With regard to claim 1, Ogihara discloses, generally in Fig. 1,
1. (Original) A method comprising:
[1] depositing a stimulus responsive polymer (SRP) 4 [i.e. “heat-decomposable polymer 4” (title, abstract, ¶ 108)] on a substrate 1 [i.e. “semiconductor substrate 1” (¶ 108)],
[2] wherein the SRP 4 comprises a homopolymer [¶¶ 44-68], and
[3a] wherein the homopolymer comprises
[3b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [¶ 67] and
[3c] a ceiling temperature less than about 300°C [¶¶ 28, 111, 118, 126, 128, 131, 134],
[4] thereby forming a film 4 on a surface of the substrate 1.
With regard to claims 2 and 3, Ogihara further discloses,
2. (Original) The method of claim 1, wherein said depositing comprises
[1] depositing a formulation comprising the SRP, and
[2] wherein the formulation comprises a solvent [¶¶ 93-95], a plasticizer, an organic acid having a pKa more than or equal to 1, a photoacid generator, a thermal acid generator [¶¶ 89-91], and/or a dye.
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 [¶ 67].
With regard to claims 26 and 27, Ogihara further discloses,
26. (Original) A structure comprising:
[1] a semiconductor substrate 1 having a top surface and a bottom surface [¶ 108]; and
[2] a layer of a stimulus responsive polymer (SRP) 4 [¶ 108] comprising a homopolymer [¶¶ 44-68],
[3] wherein the layer 4 is disposed on the top surface and/or the bottom surface of the semiconductor substrate 1 [as shown in Fig. 1], and
[4a] wherein the homopolymer 4 comprises
[4b] a molecular weight of from about 250 g/mol to about 1500 kg/mol [¶ 67] and
[4c] a ceiling temperature less than about 300°C [¶¶ 28, 111, 118, 126, 128, 131, 134].
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 [¶ 67].
VI. 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 18 is rejected under 35 U.S.C. 103 as being unpatentable over Moore.
Claim 18 reads,
18. (Original) The method of claim 1, wherein the homopolymer comprises a structure of formula (Ib):
PNG
media_image4.png
202
264
media_image4.png
Greyscale
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;
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.
Each of the limitations of claim 18 except for the last, i.e. “n1 is from 1 to 100”, has been addressed above with formula (I) of Moore. As noted above, 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.)
VII. Pertinent Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
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, is cited for disclosing the ceiling temperature of the SRP, poly(4,5- dichlorophthalaldehyde) (e.g. at Fig. 6 on p. 3256), which is the same SRP used in US 2016/0086829 (“Limary”), a prior art reference cited in the IDS filed 04/21/2023 (Limary: Fig. 5B).
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Wael Fahmy can be reached on 571-272-1705. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
Signed,
/ERIK KIELIN/
Primary Examiner, Art Unit 2814