DETAILED ACTION
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 .
Response to Amendment
Examiner acknowledges the amendments to claims 4, 7-9, and 12. No new matter has been introduced.
Response to Arguments
Applicant's arguments filed 08/29/2025 have been fully considered but they are not persuasive. Regarding the argument of unexpected results with respect to claims 1-22, Examiner would like to point out prior art reference Ichikawa et al. ‘566 teaches photoresist compositions with the salt formula of (I-Pa) [007] gives good line edge roughness [0047] wherein the cation is an organic cation such as an iodonium [0022] and carboxylate anions exemplified in [0021]. Further, Komuro et al. ‘376 teaches the anion of the salt according to any one of [1] to [5] may be a carboxylic acid anion [0030] and further exemplified in [0250]. Therefore, it would have been obvious at the time of filing to have combined the carboxylate anion of Ichikawa et al. ‘566 with the iodonium cation of Komuro et al. ‘376 to result in a resist pattern with satisfactory CD uniformity (CDU) (Komuro et al. ‘376 [0941]) and good line edge roughness (Ichikawa et al. ‘566 [0047]). Furthermore, the argument regarding unexpected results with respect to claims 1-22 is insufficient to overcome the rejections as set forth in the previous Office action because the showing is not commensurate in scope with the claimed invention.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 7-10, and 14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 6-9, and 11 of copending Application No. 18/051,050 (reference application: US 20230152693 A1).
Although the claims at issue are not identical, they are not patentably distinct from each other because the cation structure of the claimed carboxylate is similar as claimed in claim 1 of both applications and the anion structure of the claimed carboxylate copending Application No. 18/051,050 claims in claim 1 a carboxylate represented by formula (I):
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wherein R4, R5, R7 and R8 each independently represent a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, each of the hydrocarbon group may have a substituent, and a —CH2— included in each of the haloalkyl group and the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—, A1 and A2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms, each of the hydrocarbon group may have a substituent, and —CH2— included in each of the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other, m5 represents an integer of 0 to 5, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other, m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other, in which 1≤m1+m7≤5, 0≤m2+m8≤5, X0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO2—, Rbb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, X10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**, Ph represents a phenylene group which may have a substituent, Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, * represents a bonding site to carbon atoms to which Rbb1 is bonded, ** represents a bonding site to L10, and L10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH2— included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO2— or —CO—. Further, instant claims 7-10 and 14 are similarly claimed to claims 6-9 and 11 of copending Application No. 18/051,050, respectively.
The cation of the carboxylate of both the instant application and copending Application No. 18/051,050 are very similar and therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected a compound with similar structure as it would function similarly in producing a resist with satisfactory pattern collapse margin (PCM) as disclosed by the reference [0271] because chemical compounds having very close structural similarities and similar utilities has been held to be a prima facie case of obviousness. See MPEP 2144.09(I) and In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-6 and 13-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6, 12-20 and 22 of copending Application No. 18/187,103 (reference application: US 20230305395 A1) and in further view of Ichikawa et al. (US 20110014566 A1).
Although the claims at issue are not identical, they are not patentably distinct from each other because the cation structure of the claimed carboxylate is the same as claimed in claim 1 of both applications and the anion structure of the claimed carboxylate copending Application No. 18/187,103 claims in claim 1 a carboxylate represented by formula (I):
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wherein R1 and R2 each represent a hydroxy group, etc.; R4, R5, R7 and R8 each represent a halogen atom, etc.; R10 represents an acid-labile group; A1 and A2 each represent a hydrocarbon group; m1 represents an integer of 1 to 5, m2 and m8 represent an integer of 0 to 5, m4, m5 and m7 represents an integer of 0 to 4, 1≤m1+m7≤5, 0≤m2+m8≤5. Further, instant claims 2-6 and 13-22 are similarly claimed to claims 2-6, 12-20, and 22 of copending Application No. 18/187,103, respectively. However, copending Application No. 18/187,103 fails to claim the carboxylic acid anion of the instant application (claim 1).
Ichikawa et al. teaches a salt represented by the formula (I-Pa):
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wherein XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by –O– or –CO–, YPa represents a polymerizable group, and ZPa+ represents an organic cation [0013] (claim 1).
It would have been obvious to one of ordinary skill in the art at the time to have combined the cation of copending Application No. 18/187,103 with the anion of Ichikawa et al. because when used in a photoresist composition it “provides a photoresist pattern having good resolution, good LER and good focus margin” [0238]. See MPEP § 2143, rationales (A). See also KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007).
This is a provisional nonstatutory double patenting rejection.
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 (i.e., changing from AIA to pre-AIA ) 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, 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-20 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (US 20210371376 A1) in view of Ichikawa et al. (US 20110014566 A1).
Komuro et al. teaches a salt [0012] for use as an acid generator in a resist composition [0032] represented by formula (I):
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wherein R1 and R2 each independently represent a hydroxy group, —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10; L1 represents an alkanediyl group having 1 to 6 carbon atoms; R4, R5, R7 and R8 each independently represent a halogen atom, an alkyl fluoride group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—; R10 represents an acid-labile group; X1 and X2 each independently represent an oxygen atom or a sulfur atom; m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other; m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other; m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other; m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other; m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other; m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other; in which 1≤m1+m7≤5, 0≤m2+m8≤5; and AI− represents an organic anion [0013-0025]. The cation of the salt is exemplified as (I-c-1) to (I-c-54) (pgs. 11-18) with some examples including:
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or
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or
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or
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(claim 1, 6, 13, and 15) . The resist composition comprising of the acid generator salt further comprises of a resin having an acid-labile group [0033] (claims 14 and 16) wherein the resin having an acid-labile group includes at least one of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):
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and
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wherein La1 and La2 each independently represent —O— or *—O—(CH2)k1—CO—O—, k1 represents an integer of 1 to 7, and * represents a bond to —CO—; Ra4 and Ra5 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom; Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups; m1 represents an integer of 0 to 14; n1 represents an integer of 0 to 10; and n1′ represents an integer of 0 to 3 [0033-0039] (claim 17-19) and further includes an acid-labile group represented by formula (a2-A):
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wherein Aa50 represents a single bond or *—Xa51-(Aa52-Xa52)nb— and * represents a bond to carbon atoms to which —Ra50 is bonded; Aa52 represents an alkanediyl group having 1 to 6 carbon atoms; Xa51 and Xa52 each independently represent —O—, —CO—O— or —O—CO—; nb represents 0 or 1; and mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of Ra51 may be the same or different from each other [0042-0046] (claim 20). Further, the resist composition as explained above further comprises a method for producing a resist pattern, which comprises of: (1) a step of applying the resist composition according to any one of [12] to [14] on a substrate, (2) a step of drying the applied resist composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of developing the heated composition layer [0046-0051] (claim 22). However, Komuro et al. fails to teach the anion of the instant formula (I) of claim 1.
Ichikawa et al. teaches a salt represented by the formula (I-Pa):
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wherein XPa represents a single bond or a C1-C4 alkylene group, RPa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by –O– or –CO–, YPa represents a polymerizable group, and ZPa+ represents an organic cation [0013] (claim 1). Exemplified anions include:
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,
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,
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,
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, and
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[0021] (claims 2-4, 7-12).
It would have been obvious to one of ordinary skill in the art at the time to have combined the salt of Komuro et al. with the anion of Ichikawa et al. because when used in a photoresist composition it “provides a photoresist pattern having good resolution, good LER and good focus margin” [0238]. See MPEP § 2143, rationales (A). See also KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007).
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (US 20210371376 A1) in view of Ichikawa et al. (US 20110014566 A1) as applied to claims 1 and 15 above, herein referred to as Ichikawa 1, and further in view of Ichikawa et al. (US 20100230136 A1), herein referred to as Ichikawa 2.
Komuro et al. in view of Ichikawa 1 teach the salt for use as an acid generator in a resist composition, as applied to claims 1 and 15 and explained above, however, fail to teach instant claim 21 wherein the resist composition further comprises of a salt represented by formula (B1):
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(wherein the variables are defined in claim 21).
Ichikawa 2 teaches a method for producing a resist pattern having excellent shape comprising of a resist film composition comprising of a photoacid generator (A) represented by a formula (I):
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wherein Q1 and Q2, respectively and independently, represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms; X1 represents a single bond or –[CH2]k–, a methylene group contained in the –[CH2]k– may be substituted by an oxygen atom and/or a carbonyl group, a hydrogen atom contained in the –[CH2]k– may be substituted by a straight or branched aliphatic hydrocarbon group having 1 to 4 carbon atoms; k represents an integer of 1 to 17; Y1 represents an alicyclic hydrocarbon group having 4 to 36 carbon atoms, which may have a substituent; Z+ represents an organic cation [0092].
It would have been obvious to one of ordinary skill in the art at the time to have combined the resist composition of Komuro et al. in view of Ichikawa 1 to include the salt of Ichikawa 2 in the resist composition because the use of “compounds represented by a formula (I)…are preferable because a photoacid generator that imparts a chemical amplification resist composition showing excellent resolution and pattern shape is obtained” [0136]. See MPEP § 2143, rationales (A). See also KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Thackeray et al. (US 8932797 B2) teaches photoacid generators (PAGs) that are salts of onium cations, such as diphenyliodonium cations, for use in photoresist compositions of which a preferred formula is formula (III):
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wherein X is I or S and each R3 is independently a single bond to an adjacent phenyl group, hydroxy, nitrile, halogen, C1-10 alkyl, C1-10 fluoroalkyl, C1-10 alkoxy, C1-10 fluoroalkoxy, C6-20 aryl, C6-20 fluoroaryl, C6-20 aryloxy, C6-20 fluoroaryloxy, C1-20 alkylene, or C1-20 alkoxylene group; p is 2 or 3, wherein when X is I, p is 2, and where X is S, p is 2 or 3; and q is independently an integer from 0 to 5, and s and t are independently an integer from 0 to 4. It will be further appreciated that in formula (III), where X is S and p is 2, at least one [R3] is an C1-20 alkylene or C1-20 alkoxylene group connecting an aryl group to X (column 4, lines 25-35). An exemplary PAG cation (column 9) includes:
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. Thackeray et al. teaches a majority of the claim limitations regarding formula (I) of independent instant claim 1, however, fails to teach R1 and R2 as being represented by a hydroxy group, *-O-R0,*-O-CO-O-R1or*-O-L'0-CO-O-R10, and * represents a bonding site to the benzene ring, L10 represents an alkanediyl group having 1 to 6 carbon atoms, R10 represents an acid-labile group. Similarly, Thackeray et al. teaches another exemplary cationic structure:
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wherein R'' is independently H, OH, halogen, C1-20 alkyl, C1-20 fluoroalkyl, C1-20 alkoxy, C1-20 fluoroalkoxy, C3-20 cycloalkyl, C3-20 fluorocycloalkyl, C6-20 aryl, C7-20 alkyl-aryl, or a combination comprising at least one of the foregoing (column 15, lines 26-30). Once more, though the structure is similar to that of formula (I) of independent instant claim 1, Thackeray et al. fails to teach A1 and A2 to be a hydrocarbon group having 2 to 20 carbon atoms wherein the hydrocarbon group may have a substituent, and -CH2- included in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-.
Fujiwara et al. (US 20220127225 A1) teaches an onium salt serving as an acid diffusion inhibitor in a chemically amplified resist composition to for a pattern with minimal defects and excellent lithography performance factors such as CDU, LWR, and DOF (abstract). Examples of the cation in the onium salt include:
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and
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(pg. 31, [0062]) wherein the structures fail to teach the claim limitations of instant claim 1 because A1 and A2 do not contain at least 2 carbon atoms and R1 fails to be represented by a hydroxy group, *-O-R0,*-O-CO-O-R1or*-O-L'0-CO-O-R10, and * represents a bonding site to the benzene ring, L10 represents an alkanediyl group having 1 to 6 carbon atoms, R10 represents an acid-labile group.
THIS ACTION IS MADE FINAL. 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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Christine Curiac whose telephone number is (703)756-1375. The examiner can normally be reached M-F 9:00-6:00 ET.
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, Mark Huff can be reached at (571) 272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CHRISTINE CURIAC/ Examiner, Art Unit 1737
/MARK F. HUFF/ Supervisory Patent Examiner, Art Unit 1737