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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 1/20/2026; 2/13/2026 and 3/12/2026 has been entered. Claims 3 and 29 are amended; claims 6-7, 9-10, 17, 19, 21-24 and 28 are cancelled; claims 16, 18, 20 are withdrawn from consideration as being drawn to non-elected invention; and claims 30-31 are added. Accordingly, claims 1-5, 8, 11-16, 18, 20, 25-27 and 29-31 are currently pending in the application.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 1-5, 8, 11-15, 25 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over unpatentable over Harufuji et al (JP 2000-273402 A) in view of Maeso et al (US 2018/0215973 A1).
It is noted that JP 2000-273402 A is in Japanese. A copy of the machine translation into English is provided with Office action mailed 11/25/2024. All line/paragraph citations in the body of rejection below are to the English translation unless explicitly stated.
Regarding claims 1 and 27, Harufuji et al disclose, in example 6, a composition comprising TB1741 (i.e., ethyl α-cyanoacrylate and reads on cyanoacrylate component in present claim 1), EPEG (i.e., ethyl phthalyl ethyl glycolate and is a plasticizer), (EtCP) CpFe (i.e., ethyl ferrocene and reads on metallocene component in present claim 1) and Irg1700 (i.e., Irgacure 1700; see Table 1 and paragraph 0038). It is noted that Irgacure1700 is a mixture of bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one (see paragraph 0031 of present application) and reads on the at least one photoinitiator in present claims 1 and 27. Plasticizing agents are included in amounts of 10 to 70 wt% (claim 2) which overlaps with the amount of plasticizer in present claim 1.
Harufuji et al are silent with respect to the claimed species of plasticizer.
However, Harufuji et al in the general disclosure teach that examples of plasticizers include alkyl and alkenyl esters (paragraph 0013). Additionally, Maseo et al in the same filed of endeavor teach cyanoacrylate compositions (abstract) which may further comprise a plasticizing agent (paragraph 0127) such as dimethyl adipate (paragraph 0128). It is noted that dimethyl adipate is represented by formula
PNG
media_image1.png
200
400
media_image1.png
Greyscale
(i.e., reads on plasticizer in present claim 1). Case law holds that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Maseo et al, case law and given that Harufuji et al contemplate including in its composition plasticizers such as alkyl and alkenyl esters, it would have been obvious to one skilled in art prior to the filing of present application to include the plasticizers, of Maseo et al, in the cyanoacrylate compositions, of Harufuji et al, absent evidence to the contrary.
Regarding claims 2, 3, 4, and 5, examples of plasticizers, in Harufuji et al, include alkyl and alkenyl esters such as dialkyl malonate and dialkyl succinate (paragraph 0013) which reads on alkylene compound having a plurality of alkyl esters in present claim 2, alkylene compound having 4 carbon atoms in present claim 3, alkylene compound having a straight chain in present claim 4, and alkylene compound have 2 substituents in present claim 5.
Regarding claim 8, Harufuji et al teach that plasticizer is present in amounts of 10 to 70% (paragraph 0014) which reads on amount of plasticizer in present claim 8.
Regarding claims 11, 12, 13 and 15, Harufuji et al teach that additives such as heat stabilizers (i.e., reads on the stabilizer in present claim 11), photocuring accelerators (i.e., reads on accelerator component in present claim 13), radical polymerization inhibitor (i.e., reads on free radical inhibitor in present claim 12) and tougheners may be added (paragraph 0028) which reads on the toughener in present claim 15. Additionally, Maseo et al teach including acid stabilizer (paragraph 0051) which reads on the acidic stabilizer in present claim 12.
Regarding claim 14, Maseo et al teach that compositions may include accelerating agents such as crown ethers (paragraphs 0119-0120).
Regarding claim 25, Harufuji et al teach that metallocene is represented by formula: wherein M represents a transitional metal of group VIII, and “a” represents an integer of 0 to 5. Examples of the metal include iron (paragraphs 0017-0020). When n = 0, and M = Fe, it reads on ferrocene in present claim 25.
Claim 26 is rejected under 35 U.S.C. 103 as being unpatentable over Harufuji et al (JP 2000-273402 A) in view of Maeso et al (US 2018/0215973 A1) and Loth et al (US 2008/0287574 A1).
The discussion with respect to Harufuji et al in view of Maeso et al in paragraph 8 above is incorporated here by reference.
Harufuji et al and Maeso et al are silent with respect to species of the photoinitiator.
However, Loth et al in the same field of endeavor teach curable compositions suitable as adhesives (abstract). A suitable adhesive contains at least one cyanoacrylate monomer component such as ethyl cyanoacrylate (paragraph 0028). At least one photoinitiator is included in the composition. It is preferred that upon irradiation with light having a wavelength of 215 to 480 nm, it is capable of initiating a radical polymerization of olefinically unsaturated double bonds. Examples of photoinitiators include Darocur® 4265 and Darocur® TPO (paragraphs 0225-0227). It is noted that Darocur® 4265 is 2,4,6-trimethylbenzoylphenyl phosphine oxide (i.e., reads on photoinitiator in present claim 26). Case law holds that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Loth et al and case law, it would have been obvious to one skilled in art prior to the filing of present application to include the photoinitiator, of Loth et al, such as 2,4,6-trimethylbenzoylphenyl phosphine oxide in the composition, of Harufuji et al in view of Maeso et al, absent evidence to the contrary.
Claim 29 is rejected under 35 U.S.C. 103 as being unpatentable over Harufuji et al (JP 2000-273402 A) in view of Maeso et al (US 2018/0215973 A1) and Loth et al (US 2008/0287574 A1).
Harufuji et al disclose, in example 6, a composition comprising TB1741 (i.e., ethyl α-cyanoacrylate and reads on ethyl cyanoacrylate in present claim 29), EPEG (i.e., ethyl phthalyl ethyl glycolate and is a plasticizer), (EtCP) CpFe (i.e., ethyl ferrocene) and 0.2 parts by weight of Irg1700 (i.e., Irgacure 1700; see Table 1 and paragraph 0038). Plasticizing agents are included in amounts of 10 to 70 wt% (claim 2) which overlaps with the amount of plasticizer in present claim 29. The metallocene is represented by formula: wherein M represents a transitional metal of group VIII, and “a” represents an integer of 0 to 5. Examples of the metal include iron (paragraphs 0017-0020). When n = 0, and M = Fe, it reads on ferrocene in present claim 29. Metallocene is included in amounts of 100 to about 10000 ppm (paragraph 0022) which is equivalent to 0.01 to 1% by weight (i.e., reads on the amount of ferrocene in present claim 29).
Harufuji et al are silent with respect to the claimed species of plasticizer; and species of photoinitiator.
However, regarding species of plasticizer, Harufuji et al in the general disclosure teach that examples of plasticizers include alkyl and alkenyl esters (paragraph 0013). Additionally, Maseo et al in the same filed of endeavor teach cyanoacrylate compositions (abstract) which may further comprise a plasticizing agent (paragraph 0127) such as dimethyl adipate (paragraph 0128). It is noted that dimethyl adipate is represented by formula
PNG
media_image1.png
200
400
media_image1.png
Greyscale
(i.e., reads on plasticizer dimethyl adipate in present claim 29). Case law holds that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Maseo et al, case law and given that Harufuji et al contemplate including in its composition plasticizers such as alkyl and alkenyl esters, it would have been obvious to one skilled in art prior to the filing of present application to include the plasticizers, of Maseo et al, in the cyanoacrylate compositions, of Harufuji et al, absent evidence to the contrary.
Regarding species of photoinitiator, Loth et al in the same field of endeavor teach curable compositions suitable as adhesives (abstract). A suitable adhesive contains at least one cyanoacrylate monomer component such as ethyl cyanoacrylate (paragraph 0028). At least one photoinitiator is included in the composition. It is preferred that upon irradiation with light having a wavelength of 215 to 480 nm, it is capable of initiating a radical polymerization of olefinically unsaturated double bonds. Examples of photoinitiators include Darocur® 4265 and Darocur® TPO (paragraphs 0225-0227). It is noted that Darocur® 4265 is 2,4,6-trimethylbenzoylphenyl phosphine oxide (i.e., reads on photoinitiator in present claim 26). Case law holds that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Loth et al and case law, it would have been obvious to one skilled in art prior to the filing of present application to include the photoinitiator, of Loth et al, such as 2,4,6-trimethylbenzoylphenyl phosphine oxide in the composition, of Harufuji et al in view of Maeso et al, absent evidence to the contrary
Claims 1-5, 8, 11, 13, 15, 25, 27 and 30 are rejected under 35 U.S.C. 103 as being unpatentable over unpatentable over Harufuji et al (JP 2000-273402 A) in view of Greff et al (US 6,191,202 B1).
It is noted that JP 2000-273402 A is in Japanese. A copy of the machine translation into English is provided with Office action mailed 11/25/2024. All line/paragraph citations in the body of rejection below are to the English translation unless explicitly stated.
Regarding claims 1, 27 and 30, Harufuji et al disclose, in example 6, a composition comprising TB1741 (i.e., ethyl α-cyanoacrylate and reads on cyanoacrylate component in present claim 1), EPEG (i.e., ethyl phthalyl ethyl glycolate and is a plasticizer), (EtCP) CpFe (i.e., ethyl ferrocene and reads on metallocene component in present claim 1) and Irg1700 (i.e., Irgacure 1700; see Table 1 and paragraph 0038). It is noted that Irgacure1700 is a mixture of bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one (see paragraph 0031 of present application) and reads on the at least one photoinitiator in present claims 1 and 27. Plasticizing agents are included in amounts of 10 to 70 wt% (claim 2) which overlaps with the amount of plasticizer in present claim 1.
Harufuji et al are silent with respect to the claimed species of plasticizer.
However, Greff et al in the same field of endeavor teach alkyl cyanoacrylate compositions comprising at least one biocompatible plasticizer preferably acyl trialkyl citrate (abstract). The term “biocompatible plasticizer” refers to any material which is soluble or dispersible in alkyl cyanoacrylate which increases the flexibility of resulting polymer and specific examples include acetyl tri-n-butyl citrate (col. 4, lines 30-39) which is a homolog of acetyl triethyl citrate in present clams 1 and 30. Case law holds that structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093-95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers); In re Wilder, 563 F.2d 457, 460, 195 USPQ 426, 429 (CCPA 1977) (adjacent homologs and structural isomers). Therefore, in light of the teachings in Greff et al and case law, it would have been obvious to one skilled in art prior to the filing of present application to include a homolog of the plasticizer, of Greff et al, in the cyanoacrylate compositions, of Harufuji et al, for above mentioned advantages.
Regarding claims 2, 3, 4, and 5, examples of plasticizers, in Harufuji et al, include alkyl and alkenyl esters such as dialkyl malonate and dialkyl succinate (paragraph 0013) which reads on alkylene compound having a plurality of alkyl esters in present claim 2, alkylene compound having 4 carbon atoms in present claim 3, alkylene compound having a straight chain in present claim 4, and alkylene compound have 2 substituents in present claim 5.
Regarding claim 8, Harufuji et al teach that plasticizer is present in amounts of 10 to 70% (paragraph 0014) which reads on amount of plasticizer in present claim 8.
Regarding claims 11, 13 and 15, Harufuji et al teach that additives such as heat stabilizers (i.e., reads on the stabilizer in present claim 11), photocuring accelerators (i.e., reads on accelerator component in present claim 13) and tougheners may be added (paragraph 0028) which reads on the toughener in present claim 15.
Regarding claim 25, Harufuji et al teach that metallocene is represented by formula: wherein M represents a transitional metal of group VIII, and “a” represents an integer of 0 to 5. Examples of the metal include iron (paragraphs 0017-0020). When n = 0, and M = Fe, it reads on ferrocene in present claim 25.
Claims 1-5, 8, 11, 13, 15, 25, 27 and 31 are rejected under 35 U.S.C. 103 as being unpatentable over unpatentable over Harufuji et al (JP 2000-273402 A) in view of Bocqué et al (Journal of Polymer Science, Part A: Polymer Chemistry; vol. 54; pages 11-33; Year: 2016).
It is noted that JP 2000-273402 A is in Japanese. A copy of the machine translation into English is provided with Office action mailed 11/25/2024. All line/paragraph citations in the body of rejection below are to the English translation unless explicitly stated.
Regarding claims 1, 27 and 31, Harufuji et al disclose, in example 6, a composition comprising TB1741 (i.e., ethyl α-cyanoacrylate and reads on cyanoacrylate component in present claim 1), EPEG (i.e., ethyl phthalyl ethyl glycolate and is a plasticizer), (EtCP) CpFe (i.e., ethyl ferrocene and reads on metallocene component in present claim 1) and Irg1700 (i.e., Irgacure 1700; see Table 1 and paragraph 0038). It is noted that Irgacure1700 is a mixture of bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one (see paragraph 0031 of present application) and reads on the at least one photoinitiator in present claims 1 and 27. Plasticizing agents are included in amounts of 10 to 70 wt% (claim 2) which overlaps with the amount of plasticizer in present claim 1.
Harufuji et al are silent with respect to the claimed species of plasticizer.
However, Bocqué et al teach that common plasticizers are suspected to produce bio-accumulation in the environment. With the growing interest for plasticizers with low migration levels and low toxicity as an alternative to phthalates, researchers are paying attention to biobased plasticizers made from citrates (introduction). The primary role of plasticizers is to enhance flexibility and processability of polymers (page 13, col. 1; first full paragraph). Examples of citrate based plasticizers include
PNG
media_image2.png
62
116
media_image2.png
Greyscale
(see Figure 5; page 21) which reads on triethyl O-citrate in present claims 1 and 31. Case law holds that selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Bocqué et al and case law, it would have been obvious to one skilled in art prior to the filing of present application to include the citrate based plasticizer such as triethyl O-citrate, of Bocqué et al, in the composition, of Harufuji et al, for above mentioned advantages.
Regarding claims 2, 3, 4, and 5, examples of plasticizers, in Harufuji et al, include alkyl and alkenyl esters such as dialkyl malonate and dialkyl succinate (paragraph 0013) which reads on alkylene compound having a plurality of alkyl esters in present claim 2, alkylene compound having 4 carbon atoms in present claim 3, alkylene compound having a straight chain in present claim 4, and alkylene compound have 2 substituents in present claim 5.
Regarding claim 8, Harufuji et al teach that plasticizer is present in amounts of 10 to 70% (paragraph 0014) which reads on amount of plasticizer in present claim 8.
Regarding claims 11, 13 and 15, Harufuji et al teach that additives such as heat stabilizers (i.e., reads on the stabilizer in present claim 11), photocuring accelerators (i.e., reads on accelerator component in present claim 13) and tougheners may be added (paragraph 0028) which reads on the toughener in present claim 15.
Regarding claim 25, Harufuji et al teach that metallocene is represented by formula: wherein M represents a transitional metal of group VIII, and “a” represents an integer of 0 to 5. Examples of the metal include iron (paragraphs 0017-0020). When n = 0, and M = Fe, it reads on ferrocene in present claim 25.
Response to Arguments
The rejections under 35 U.S.C. 112 and 103 as set forth in paragraphs 4 and 9-11, of Office action mailed 11/12/2025, are withdrawn in view of amendment and/or applicant arguments and/or new grounds of rejection set forth in this Office action, necessitated by amendment.
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 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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KARUNA P REDDY whose telephone number is (571)272-6566. The examiner can normally be reached 8:30 AM to 5:00 PM M-F.
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, Arrie (Lanee) Reuther can be reached at 571-270-7026. 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.
/KARUNA P REDDY/Primary Examiner, Art Unit 1764
Prosecution Insights