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 Election/Restrictions
Applicant's timely election with traverse of Group I, claims 1-12 and 15, in the reply filed 05/22/2026 is acknowledged.
The traversal is on the ground(s) that the prior art Shirasaka (JP 2013076089 A) fails to disclose a crosslinker ''which comprises at least one acid-functional group derived from phosphoric acid and at least one radically (co)polymerizable reactive group," as recited in Claim 1, component (b) (p. 2, last para). Applicant also argues that the Office maps "isocyanuric acid-modified bifunctional (meth)acrylate" to the claimed "ethylenically unsaturated acidic compound" of component (a)(ii); however, isocyanuric acid-modified bifunctional (meth)acrylates are crosslinking monomers bearing isocyanurate ring structures; these are not ethylenically unsaturated acidic compounds in the sense of the claims (p. 3, 2nd para). Applicant also argues that Claim 1 further requires that the ethylenically unsaturated acidic compound (a)(ii) "does not comprise an acid-functional group derived from phosphoric acid," a negative limitation that the Office has not addressed with respect to Shirasaka (p. 3, 2nd para).
In response, Applicant's arguments are not persuasive.
Shirasaka teaches an adhesive composition comprising a radical polymerizing compound and a nitroxide compound ([0009]). Shirasaka teaches that the radical polymerizing compound preferably contains a (meth)acryloyl group ([0034]), and the radical polymerizing compound can comprise an isocyanuric acid-modified bifunctional (meth)acrylate ([0035]).
The “Isocyanuric Acid Information” as an evidentiary reference shows that isocyanuric acid has pH of 4.5 (p. 2, § 2.2 Physical-Chemical Properties). Thus, isocyanuric acid is an acid. Thus, the isocyanuric acid-modified bifunctional (meth)acrylate in Shirasaka reads on the claimed ethylenically unsaturated acidic compound, and reads on the claimed ethylenically unsaturated acidic compound not comprising an acid-functional group derived from phosphoric acid.
Shirasaka also teaches that the adhesive composition comprises an adhesive aid ([0064]), and the adhesive aid can be a phosphate ester derivative represented by the general formula (F):
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wherein R18 represents a hydrogen atom or methyl group, “n” represents an integer of 1 to 10, and “m” represents an integer of 1 or 2 ([0067]-[0068]), which reads on the claimed crosslinker comprising at least one acid-functional group derived from phosphoric acid and at least one radically (co)polymerizable reactive group.
Thereby the restriction requirement is still deemed proper and is therefore made FINAL.
Clams 1-15 are currently pending. Claims 13 and 14 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected inventions, there being no allowable generic or linking claim.
Therefore, claims 1-12 and 15 are currently under examination.
Claim Objections
Claim 8 is objected to because of the following informalities:
Claim 8 recites “a thermally conductive particles”. Applicant is suggested to revise it as “a thermally conductive particle” for clarity.
Appropriate correction is required.
Claim Rejections - 35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claim 15 is rejected under 35 U.S.C. 101 because the claimed invention is directed to non-statutory subject matter. The claim(s) does/do not fall within at least one of the four categories of patent eligible subject matter because it is a “use” claim. See MPEP 2173.05(q).
Appropriate correction is required.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 15 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 15 merely recites a "use" of the claimed composition and is indefinite for not reciting any active, positive steps delimited how this use is actually practiced. See MPEP 2173.05(q).
Appropriate correction is required.
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, 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.
1. Claims 1-5, 7-10, 12, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Shirasaka (JP 2013076089 A, hereinafter Shirasaka) as evidenced by “Isocyanuric Acid Information” (“Isocyanuric Acid: Review of Toxicological Literature”, from National Institute of Environmental Health Sciences, 1997, hereinafter “Isocyanuric Acid Information”).
Regarding claims 1 and 2, Shirasaka teaches an adhesive composition comprising a radical polymerizing compound and a nitroxide compound ([0009]). Shirasaka also teaches that the adhesive composition can be cured ([0010]). Thus, the adhesive composition of Shirasaka reads on the claimed curable precursor.
Shirasaka teaches that the radical polymerizing compound preferably contains a (meth)acryloyl group ([0034]), and the radical polymerizing compound can comprise an isocyanuric acid-modified bifunctional (meth)acrylate ([0035]).
The “Isocyanuric Acid Information” as an evidentiary reference shows that isocyanuric acid has pH of 4.5 (p. 2, § 2.2 Physical-Chemical Properties). Thus, isocyanuric acid is an acid. Thus, the isocyanuric acid-modified bifunctional (meth)acrylate in Shirasaka reads on the claimed ethylenically unsaturated acidic compound, and reads on the claimed ethylenically unsaturated acidic compound not comprising an acid-functional group derived from phosphoric acid.
Shirasaka also teaches that the adhesive composition comprises a flow-enhancing agent, wherein the flow-enhancing agent is a monofunctional (meth)acrylate, and the flow-enhancing agent can comprise 2-ethylhexyl (meth)acrylate ([0071]). Shirasaka also teaches that the flow-enhancing agent improves fluidity of the adhesive composition during connection ([0071]). Thus, the 2-ethylhexyl (meth)acrylate in Shirasaka reads on the claimed C1-C32 (meth)acrylic acid ester monomers, and reads on the claimed C1-C32 (meth)acrylic acid ester monomers not comprising functional groups other than the (meth)acrylic acid ester groups.
Thus, the combination of the radical polymerizing compound which contains a (meth)acryloyl group and the flow-enhancing agent which is a monofunctional (meth)acrylate as taught by Shirasaka reads on the claimed radically (co)polymerizable (meth)acrylate-based component.
Shirasaka further teaches that the adhesive composition comprises an adhesive aid ([0064]), and the adhesive aid can be a phosphate ester derivative represented by the general formula (F):
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wherein R18 represents a hydrogen atom or methyl group, “n” represents an integer of 1 to 10, and “m” represents an integer of 1 or 2 ([0067]-[0068]), which reads on the claimed crosslinker comprising at least one acid-functional group derived from phosphoric acid and at least one radically (co)polymerizable reactive group.
Shirasaka further teaches that the adhesive aid is added to improve adhesion and handling properties of the adhesive composition ([0064]).
Shirasaka does not teach a single embodiment with all the claimed elements together.
However, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to make an adhesive composition comprising a nitroxide compound and a radical polymerizing compound including an isocyanuric acid-modified bifunctional (meth)acrylate, and further comprising a flow-enhancing agent including 2-ethylhexyl (meth)acrylate, and an adhesive aid including a phosphate ester derivative represented by the general formula (F) as taught by Shirasaka, in order to improve the fluidity, adhesion and handling properties of the adhesive composition with a reasonable expectation of success, because the adhesive composition of Shirasaka comprises a radical polymerizing compound and a nitroxide compound, and can further comprise a flow-enhancing agent and an adhesive aid, the flow-enhancing agent improves fluidity of the adhesive composition during connection, the adhesive aid improves adhesion and handling properties of the adhesive composition as recognized by Shirasaka. Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art.
Regarding claim 3, Shirasaka teaches that the radical polymerizing compound preferably contains a (meth)acryloyl group ([0034]), and the radical polymerizing compound can comprise an isocyanuric acid-modified bifunctional (meth)acrylate ([0035]).
The “Isocyanuric Acid Information” as an evidentiary reference shows that isocyanuric acid has pH of 4.5 (p. 2, § 2.2 Physical-Chemical Properties). Thus, isocyanuric acid is an acid. Thus, the isocyanuric acid-modified bifunctional (meth)acrylate in Shirasaka reads on the claimed ethylenically unsaturated acidic compound comprising monomers having ethylenic unsaturation and acid functionality.
Regarding claim 4, Shirasaka teaches ([0045]) that the nitroxide compound can be the compound represented by the formula (1):
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which reads on the claimed nitroxide being 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO).
Regarding claim 5, Shirasaka teaches ([0045]) that the nitroxide compound can be the compound represented by the formula (2):
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which reads on the claimed nitroxide being 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPOL).
Regarding claim 7, Shirasaka teaches that the adhesive composition comprises a flow-enhancing agent, wherein the flow-enhancing agent is a monofunctional (meth)acrylate, and examples of the flow-enhancing agent include 2-ethylhexyl (meth)acrylate and 2-hydroxyethyl (meth)acrylate ([0071]). Shirasaka also teaches that the flow-enhancing agent can comprise two or more compounds ([0071]).
Thus, the flow-enhancing agent of Shirasaka can comprise 2-ethylhexyl (meth)acrylate and 2-hydroxyethyl (meth)acrylate. The 2-hydroxyethyl (meth)acrylate is copolymerizable with 2-ethylhexyl (meth)acrylate (the claimed C1-C32 (meth)acrylic acid ester monomers) and isocyanuric acid-modified bifunctional (meth)acrylate (the claimed ethylenically unsaturated acidic compound). Thus, the 2-hydroxyethyl (meth)acrylate in Shirasaka reads on the claimed ethylenically unsaturated monomers having a functional group and which are copolymerizable with the C1-C32 (meth)acrylic acid ester monomers (i) and the ethylenically unsaturated acidic compound (ii) of the radically (co)polymerizable (meth)acrylate-based component (a).
Regarding claim 8, Shirasaka teaches that the adhesive composition further comprises conductive particles ([0060]), wherein the conductive particles can include copper particles ([0061]), which reads on the claimed thermally conductive particle.
Regarding claim 9, Shirasaka teaches that the adhesive composition comprises a basic compound ([0009]), which reads on the claimed base.
Regarding claim 10, Shirasaka teaches that the adhesive composition comprises a basic compound ([0009]), wherein the basic compound can contain amino groups ([0052]), and the basic compound can be represented by the general formula (B):
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wherein R2, R3, and R4 can independently represent an alkyl group with a carbon number of 1 to 20 ([0053]-[0054]), which reads on the claimed base being a tertiary amine.
Regarding claim 12, Shirasaka teaches that the adhesive composition comprises a radical polymerization initiator ([0009]).
Regarding claim 15, the limitation “for adhesive applications and/or for thermal management applications in the automotive industry” is an intended use and does not add structural difference, thus the intended use is extended little patentable weight. See MPEP § 2112.02.
Shirasaka teaches that the adhesive composition is used for adhesive applications ([0016]).
2. Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Shirasaka (JP 2013076089 A, hereinafter Shirasaka) as evidenced by “Isocyanuric Acid Information” (“Isocyanuric Acid: Review of Toxicological Literature”, from National Institute of Environmental Health Sciences, 1997, hereinafter “Isocyanuric Acid Information”) as applied to claims 1-5, 7-10, 12, and 15 above, and further in view of Plenderleith (WO 2021/176023 A1, see US 2024/0199770 A1, hereinafter Plenderleith).
The disclosure of Shirasaka as evidenced by “Isocyanuric Acid Information” is relied upon as set forth above.
Regarding claim 6, Shirasaka teaches that the adhesive composition comprises a radical polymerizing compound ([0009]), wherein the radical polymerizing compound contains a (meth)acryloyl group ([0034]), and examples of the radical polymerizing compound include isocyanuric acid-modified bifunctional (meth)acrylate and polyether (meth)acrylate oligomer ([0035]). Shirasaka also teaches that the radical polymerizing compound can be used in combination with two or more compounds ([0035]).
Thus, the radical polymerizing compound of Shirasaka can comprise isocyanuric acid-modified bifunctional (meth)acrylate and polyether (meth)acrylate oligomer. The polyether (meth)acrylate oligomer contains a radically (co)polymerizable reactive group.
Shirasaka also teaches that the molecular weight can be determined by measuring it by gel permeation chromatography (GPC) analysis ([0032]).
Shirasaka does not teach that the polyether (meth)acrylate oligomer has a number average molecular weight of at least 2000 g/mol.
However, Plenderleith teaches a curable composition comprising (a) an ethylenically unsaturated compound (claim 1), wherein the ethylenically unsaturated compound can comprise a (meth)acrylate-functionalized oligomer (claim 2), and the (meth)acrylate-functionalized oligomer can be a (meth)acrylate-functionalized polyether oligomer (also called as “polyether (meth)acrylate oligomer”) (claim 8, [0082]).
Plenderleith also teaches that the (meth)acrylate-functionalized oligomer can have a number average molecular weight of from 1,000 to 5,000 g/mol (claim 7, [0081]), which overlaps with the claimed range of “at least 2000 g/mol”.
Plenderleith also teaches that the curable composition is used in an adhesive application ([0001], [0285]-[0286]).
Therefore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to provide the polyether (meth)acrylate oligomer having a number average molecular weight of from 1,000 to 5,000 g/mol as taught by Plenderleith as the polyether (meth)acrylate oligomer in Shirasaka, in order to make an adhesive composition for adhesive applications with a reasonable expectation of success, because the polyether (meth)acrylate oligomer having a number average molecular weight of from 1,000 to 5,000 g/mol is used as an ethylenically unsaturated compound in the curable composition of Plenderleith, and the curable composition of Plenderleith is used in an adhesive application as recognized by Plenderleith.
Furthermore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to expect that the polyether (meth)acrylate oligomer of Plenderleith would have a number average molecular weight of from 1,000 to 5,000 g/mol as measured by gel permeation chromatography (GPC) with a reasonable expectation of success, because the number average molecular weight is a property of the polyether (meth)acrylate oligomer; no matter what kind of method is used to measure the number average molecular weight of the polyether (meth)acrylate oligomer of Plenderleith, it will not change the fact that the polyether (meth)acrylate oligomer of Plenderleith has a number average molecular weight of from 1,000 to 5,000 g/mol as recognized by Plenderleith. Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art.
3. Claims 1, 11, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Serizawa (WO 2022/210703 A1, hereinafter Serizawa).
Regarding claims 1, 11, and 12, Serizawa teaches an adhesive composition comprising a polymerizable monomer having a carbon-carbon double bond, and a polymerization initiator ([0015], claim 1), wherein the polymerization initiator is a radical polymerization initiator ([0038]). Serizawa also teaches that the adhesive composition is cured to form a cured product ([0015], claim 1). Thus, the adhesive composition of Serizawa reads on the claimed curable precursor.
Serizawa teaches that the polymerizable monomer has a (meth)acryloyl group ([0019]); the polymerizable monomer comprises a highly polar monomer which is a polymerizable monomer having a polar functional group and a carbon-carbon double bond ([0019]), wherein the highly polar monomer can comprise a (meth)acrylic acid, and a compound having a phosphate group and a (meth)acryloyl group such as phosphate ester of 2-hydroxyethylmethacrylate ([0022], [0075]; Example 1, Table 2).
Thus, the (meth)acrylic acid in Serizawa reads on the claimed ethylenically unsaturated acidic compound, and reads on the claimed ethylenically unsaturated acidic compound not comprising an acid-functional group derived from phosphoric acid. The compound having a phosphate group and a (meth)acryloyl group such as phosphate ester of 2-hydroxyethylmethacrylate in Serizawa reads on the claimed crosslinker comprising at least one acid-functional group derived from phosphoric acid and at least one radically (co)polymerizable reactive group.
Serizawa also teaches that the polymerizable monomer comprises a monofunctional monomer ([0019], [0023]), wherein the monofunctional monomer can comprise methyl (meth)acrylate ([0026]). Thus, the methyl (meth)acrylate in Serizawa reads on the claimed C1-C32 (meth)acrylic acid ester monomers not comprising functional groups other than the (meth)acrylic acid ester groups.
Serizawa also teaches that the adhesive composition further comprises a stable radical type compound ([0045], claim 16), wherein the stable radical type compound is a nitroxide compound ([0046], claim 17). Serizawa teaches that the stable radical type compound improves the storage stability of the adhesive composition ([0045]).
Serizawa further teaches that the adhesive composition preferably comprises a reducing agent, wherein the reducing agent is preferably a transition metal salt such as cobalt naphthenate ([0040]). The transition metal salt such as cobalt naphthenate in Serizawa is not a base.
Serizawa further teaches that other components are optional, the adhesive composition is not required to contain other components ([0044]). Thus, the adhesive composition of Serizawa can contain no base compound.
Serizawa also teaches that the reducing agent reacts with the polymerization initiator to generate radicals; when the polymerization initiator and the reducing agent are used in combination, curability can be further enhanced ([0040]).
Serizawa does not teach a single embodiment with all the claimed elements together.
However, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to make an adhesive composition comprising a radical polymerization initiator, and a polymerizable monomer comprising a monofunctional monomer including methyl (meth)acrylate, and a highly polar monomer including (meth)acrylic acid, and a compound having a phosphate group and a (meth)acryloyl group such as phosphate ester of 2-hydroxyethylmethacrylate, further comprising a stable radical type compound that is a nitroxide compound, and a reducing agent that is a transition metal salt such as cobalt naphthenate as taught by Serizawa, in order to improve the storage stability and curability of the adhesive composition with a reasonable expectation of success, because the nitroxide compound as a stable radical type compound improves the storage stability of the adhesive composition, by using the polymerization initiator and the reducing agent such as cobalt naphthenate in combination, the curability of the adhesive composition is improved as recognized by Serizawa. Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JIAJIA JANIE CAI whose telephone number is 571-270-0951. The examiner can normally be reached Monday-Friday 8:30 am - 5:00 pm.
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/JIAJIA JANIE CAI/Examiner, Art Unit 1761
/MATTHEW R DIAZ/Primary Examiner, Art Unit 1761
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