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 .
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.
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 15–20, 24, and 28 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Desmaison et al. (U.S. Patent No. 7,074,315; “US’315”) in view of Sunder et al. (U.S. Patent No. 6,765,082; “US’082”), further in view of Schlifke-Poschalko (EP 2,509,576; “EP’576”), and further in view of Olin (U.S. Patent No. 3,879,475; “US’475”).
As to claim 15, US’315 teaches an electrolytic copper plating bath for depositing copper, wherein the copper plating bath comprises at least one polyglycerin compound selected from poly(1,2,3-propanetriol), poly(2,3-epoxy-1-propanol), and derivatives thereof. US’315 further teaches using the copper bath to electrodeposit a copper layer. See US’315, col. 3, lines 5–18. US’315 further teaches that the polyglycerin compounds used in the copper bath may be produced by known methods, and that glycerin, glycidol, or epichlorohydrin may be used to produce the polyglycerin compounds. US’315 teaches that these materials are polymerized under catalysis using alkaline substances, or alternatively in the presence of sulfuric acid or boron trifluoride. See US’315, col. 7, lines 20–37. US’315 also teaches that the polyglycerin compounds may be linear, branched, and/or have cyclic moieties. See US’315, col. 7, lines 50–55.
US’315 does not expressly teach reacting 2,3-epoxy-1-propanol with a nitrogen-containing compound in the presence of a catalyst to synthesize a solution comprising a linear or branched polyhydroxyl, as recited in claim 15.
US’082 teaches a process for preparing highly branched glycidol-based polyols by polymerizing glycidol in the presence of a hydrogen-active starter compound with basic catalysis. See US’082, col. 1, lines 6–10. US’082 teaches adding a dilute solution containing glycidol to a hydrogen-active starter compound in the presence of a basic catalyst, wherein each molecule possesses the initiator, i.e., the hydrogen-active starter compound, as the core unit, and the degree of polymerization is controlled by the monomer/initiator ratio. See US’082, col. 1, lines 28–44.
US’082 further teaches that the hydrogen-active starter compounds may contain hydroxyl, thiol, and/or amino groups and specifically lists nitrogen-containing starter compounds including methylamine, ethylamine, propylamine, butylamine, stearylamine, aniline, benzylamine, ammonia, ethylenediamine, and other diamines. See US’082, col. 2, lines 1–14. US’082 also teaches that the resulting polyols contain the initiator as the core unit. See US’082, col. 3, lines 18–30.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to prepare US’315’s copper-bath polyglycerin/poly(2,3-epoxy-1-propanol) derivative additive using US’082’s known glycidol polymerization method, including a nitrogen-containing starter compound, because US’315 expressly identifies poly(2,3-epoxy-1-propanol) and derivatives thereof as useful copper-bath additives and further indicates that glycidol-based polyglycerins may be prepared by known catalytic polymerization methods. US’082 supplies one such known catalytic polymerization method and teaches that the starter compound becomes the core unit of the resulting highly branched glycidol-based polyol.
A person of ordinary skill would have had a reasonable expectation of success because both references concern glycidol/polyglycerin polyhydroxyl materials, and US’082 specifically teaches controlling the polyol structure by the monomer/initiator ratio.
The step of “diluting the resulting solution” would have been obvious because US’082 teaches use of dilute glycidol solution during polymerization and teaches workup of the alkaline polymer by dissolving it in a suitable solvent, such as methanol, followed by filtration or other purification. See US’082, col. 3, lines 4–17. Diluting a polymeric additive solution to a useful concentration for subsequent handling or incorporation into a copper electroplating bath would have been a routine process step within the level of ordinary skill in the art.
Accordingly, claim 15 is unpatentable over US’315 in view of US’082.
As to claim 16, US’082 teaches that the hydrogen-active starter compound becomes the core unit of the resulting glycidol-based polyol, and that suitable starter compounds include amino-containing compounds, including amines, ammonia, and diamines. See US’082, col. 1, lines 36–40; col. 2, lines 1–14; col. 3, lines 18–30. Accordingly, US’082 teaches or suggests that the nitrogen-containing compound comprises a core containing a nitrogen species. Claim 16 is therefore unpatentable over US’315 in view of US’082.
As to claim 17, EP’576 teaches that a hyperbranched polyether-polyol backbone is obtainable by one-pot ring-opening polymerization initiated by a polyol starter unit using glycidol as an AB2-type monomer to form a hyperbranched polyether-polyol backbone carrying free hydroxyl groups. See EP’576, paragraphs [0015]–[0016]. EP’576 further teaches polyol starter units including N-methyldiethanolamine, N-ethyldiethanolamine, N,N,N′,N′-tetrakis(2-hydroxyethyl)ethylenediamine, and triethanolamine. See EP’576, paragraph [0014]. N-methyldiethanolamine, N-ethyldiethanolamine, and triethanolamine are aminic alcohols within the scope of claim 17.
It would have been obvious to use these known aminic-alcohol starter units in the glycidol polymerization method applied to US’315’s copper-bath additive because EP’576 teaches that such starter units initiate glycidol ring-opening polymerization to form hyperbranched polyether-polyol backbones. Claim 17 is therefore unpatentable over US’315 in view of US’082 and EP’576.
As to claim 18, EP’576 teaches that glycidol ring-opening polymerization may be performed using an effective amount of at least one catalyst and identifies Lewis acids, including BF3, as suitable catalysts. See EP’576, paragraph [0016]. US’475 teaches reacting aliphatic alcohols with glycidol in the presence of a polar, non-reactive, miscible solvent and a basic or acid catalyst. See US’475, col. 1, lines 52–59. US’475 further teaches that suitable Lewis acid catalysts include BF3 and its etherates, and identifies BF3·Et2O as a preferred catalyst, expressly called boron trifluoride etherate or boron trifluoride diethyl ether. See US’475, col. 3, lines 17–30.
It would have been obvious to use boron trifluoride etherate as the BF3 Lewis acid catalyst in the glycidol polymerization reaction because US’475 teaches boron trifluoride etherate as a preferred BF3 etherate catalyst for glycidol-alcohol reactions, and EP’576 teaches BF3 as a suitable catalyst for glycidol ring-opening polymerization. Use of boron trifluoride etherate in a solvent-compatible reagent solution would have been a routine catalyst-delivery choice. Claim 18 is therefore unpatentable over US’315 in view of US’082 and EP’576, and further in view of US’475.
As to claim 19, EP’576 teaches that the amount of glycidol units is selected in the range of about 5 to 12 mol equivalents per mol equivalent of the polyol starter unit, more particularly about 6 to 9 mol equivalents per mol equivalent of the polyol starter unit. See EP’576, paragraph [0010]. This corresponds to a starter:glycidol molar ratio of about 0.083 to about 0.20 for the 5–12 range, and about 0.111 to about 0.167 for the 6–9 range. These ratios fall within claim 19’s recited range of about 0.01 to 0.50. US’475 also teaches a glycidol:alcohol molar ratio of 4:1 to 14:1, preferably 6:1 to 12:1, which corresponds to an alcohol:glycidol ratio of about 0.071 to 0.25, preferably about 0.083 to 0.167. See US’475, col. 3, lines 30–39. Claim 19 is therefore unpatentable over US’315 in view of US’082 and EP’576, and further in view of US’475.
As to claim 20, the claimed molar ratio of 0.01 to 0.20 is met or at least rendered obvious by EP’576’s glycidol:starter ratio of about 5 to 12 mol equivalents of glycidol per mol equivalent of starter, corresponding to a starter:glycidol ratio of about 0.083 to about 0.20, and by US’475’s preferred glycidol:alcohol ratio of 6:1 to 12:1, corresponding to an alcohol:glycidol ratio of about 0.083 to about 0.167. See EP’576, paragraph [0010]; US’475, col. 3, lines 30–39. Claim 20 is therefore unpatentable over US’315 in view of US’082 and EP’576, and further in view of US’475.
As to claim 24, EP’576 teaches aminic-alcohol starter units including N-methyldiethanolamine, N-ethyldiethanolamine, and triethanolamine. See EP’576, paragraph [0014]. Claim 24 recites a Markush group including, among others, triethanolamine, N-methyl diethanolamine, and N-ethyl diethanolamine. Because EP’576 teaches species falling within the claimed Markush group and teaches their use as starter units for glycidol ring-opening polymerization, claim 24 is unpatentable over US’315 in view of US’082 and EP’576.
As to claim 28, US’082 teaches that the polyol may be worked up by neutralization and that the alkaline polymer can first be dissolved in a suitable solvent, such as methanol, followed by subsequent filtration or treatment with adsorbent material, particularly filtration through acidic ion-exchange material. See US’082, col. 3, lines 4–17. US’082’s Example 1 similarly teaches dissolving the reaction mixture in methanol and neutralizing by filtration through an acidic ion-exchange resin. See US’082, col. 3, lines 39–47. Filtering the solution after dilution would have been an obvious workup and purification step for a glycidol-based polyol additive solution. Claim 28 is therefore unpatentable over US’315 in view of US’082.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 15, 16, 18, 21-23, 27, and 28 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The written description requirement is not satisfied because the specification does not reasonably convey to one of ordinary skill in the art that the inventors had possession of the full scope of the claimed method at the time of filing.
Independent claim 15 recites a method of making an additive for use in a copper electroplating solution, wherein the additive comprises a linear or branched polyhydroxyl, the method comprising reacting 2,3-epoxy-1-propanol with a “nitrogen-containing compound” in the presence of “a catalyst” to synthesize a solution comprising the linear or branched polyhydroxyl, and diluting the resulting solution. Claim 16 further recites that the nitrogen-containing compound comprises a core containing a nitrogen species. Claims 18, 27, and 28 depend from claim 15 and do not further limit the nitrogen-containing compound to the disclosed aminic alcohols or ammonium alcohols.
The specification describes reacting aminic alcohols or ammonium alcohols with 2,3-epoxy-1-propanol and states that such polyhydroxyl compounds initiated by a core containing a nitrogen species can increase columnar nanotwinned copper density and help initiate nanotwinned copper more quickly than poly(2,3-epoxy-1-propanol). The specification further lists examples of aminic alcohols and ammonium alcohols and provides Example 7, in which boron trifluoride etherate in methanol is added to a solution of 2,3-epoxy-1-propanol and tri-methyldiethanolamine, followed by reaction, dilution, and filtration.
However, the disclosure of aminic alcohols, ammonium alcohols, and one specific catalyst system does not reasonably describe the full genus of “a nitrogen-containing compound” reacted in the presence of “a catalyst.” The claim language encompasses nitrogen-containing compounds having no aminic alcohol or ammonium alcohol functionality, compounds that would not act as an initiating core for the disclosed polyhydroxyl, and catalyst systems not described in the specification. The specification does not provide representative species, structural features, or common characteristics sufficient to show possession of the full breadth of the claimed nitrogen-containing compound/catalyst combination.
Claims 21-23 are further rejected under 35 U.S.C. § 112(a) because they recite that “the 2,3-epoxy-1-propanol has a molecular weight” within ranges of about 200 to about 20,000 g/mol, about 500 to about 5,000 g/mol, and about 1,000 to about 3,000 g/mol. The specification does not describe 2,3-epoxy-1-propanol as having those molecular-weight ranges. Rather, the specification describes the “linear or branched polyhydroxyl” as having a molecular weight of about 200 to about 20,000 g/mol, more preferably about 500 to about 5,000 g/mol, and most preferably about 1,000 to about 3,000 g/mol. Thus, the claimed molecular-weight limitations are not described as applying to the 2,3-epoxy-1-propanol reactant. The specification therefore fails to demonstrate possession of the subject matter of claims 21-23 as presently written.
Accordingly, claims 15, 16, 18, 21-23, 27, and 28 lack adequate written-description support.
Claims 15, 16, 18, 21-23, 27, and 28 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the enablement requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
The specification does not enable one of ordinary skill in the art to make and use the full scope of the claimed invention without undue experimentation. The claims are broader than the enabling disclosure because claim 15 broadly encompasses reacting 2,3-epoxy-1-propanol with any nitrogen-containing compound in the presence of any catalyst to form a solution comprising a linear or branched polyhydroxyl. Claim 16 further recites a core containing a nitrogen species, but does not identify the structural requirements needed for the nitrogen-containing compound to function as an initiating core. Claims 18, 27, and 28 do not cure this deficiency because they do not limit the nitrogen-containing compound to the disclosed aminic alcohols or ammonium alcohols.
The specification provides limited working guidance. The disclosure identifies aminic alcohols and ammonium alcohols as suitable nitrogen-containing compounds and provides one working synthesis example using boron trifluoride etherate in methanol and tri-methyldiethanolamine. The specification does not provide sufficient guidance for selecting nitrogen-containing compounds outside the disclosed aminic alcohol and ammonium alcohol classes, nor does it provide sufficient guidance for selecting catalyst systems across the full breadth of the claim. The disclosure also does not teach which structural features of a nitrogen-containing compound are required to produce the claimed linear or branched polyhydroxyl additive.
Application of the Wands factors support a conclusion of undue experimentation.
The breadth of the claims is substantial. Claim 15 is not limited to aminic alcohols, ammonium alcohols, quaternized aminic alcohols, or the species listed in the specification. The claim also is not limited to boron trifluoride etherate or any defined class of catalysts. The claim therefore covers a broad and diverse genus of nitrogen-containing compounds and catalyst systems.
The nature of the invention weighs in favor of undue experimentation. The claimed method involves synthesis of a polymeric electroplating additive from 2,3-epoxy-1-propanol and a nitrogen-containing compound. The identity of the nitrogen-containing compound, the catalyst, the molar ratio, reaction temperature, exotherm control, dilution, and filtration can materially affect the resulting polyhydroxyl structure and its suitability as an electroplating additive.
The state of the prior art and predictability of the art also weigh in favor of undue experimentation. Polymerization and ring-opening reactions of epoxy alcohols are sensitive to initiator, catalyst, reaction medium, temperature, and molar ratio. The specification itself indicates that the presence of certain organic electroplating compounds can disrupt the ability of the polyhydroxyl material to produce nanotwinned copper. This supports that the art is not sufficiently predictable to permit the claimed breadth without substantial screening.
The amount of direction or guidance provided in the specification is limited. The specification gives guidance for aminic alcohols and ammonium alcohols, provides specific lists of such compounds, and gives one detailed example using boron trifluoride etherate in methanol. The specification does not provide general rules or structure-function guidance that would allow one of ordinary skill in the art to select any nitrogen-containing compound and any catalyst with a reasonable expectation of producing the claimed additive.
The presence or absence of working examples weighs in favor of undue experimentation. The specification provides only a narrow working example for a nitrogen-containing additive. The number of working examples is not commensurate with the broad genus of nitrogen-containing compounds and catalysts covered by claim 15.
The quantity of experimentation required would be excessive. A person of ordinary skill would need to select and screen numerous nitrogen-containing compounds, catalyst systems, molar ratios, temperatures, reaction times, and dilution/filtration conditions to determine whether the resulting product is a linear or branched polyhydroxyl suitable for use as the claimed additive. Such experimentation would amount to more than routine optimization because the specification does not identify the structural boundaries of the claimed genus.
The relative skill in the art does not cure the deficiency. Although one of ordinary skill in the art of electroplating additive chemistry would have knowledge of polymerization and plating-bath chemistry, the disclosure still does not provide sufficient guidance to enable the full breadth of the claims without undue experimentation.
Claims 21-23 are further not enabled because they recite 2,3-epoxy-1-propanol as having molecular weights of about 200 to about 20,000 g/mol, about 500 to about 5,000 g/mol, and about 1,000 to about 3,000 g/mol. The specification does not teach how to provide or use 2,3-epoxy-1-propanol having such molecular weights. The disclosed molecular-weight ranges apply to the resulting linear or branched polyhydroxyl, not to the 2,3-epoxy-1-propanol reactant. Accordingly, claims 21-23 are not enabled as written.
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.
Claims 19-20, 21-23 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 19 recites “the molar ratio of the amine in the aminic alcohol or the ammonium alcohol to 2,3-epoxy-1-propanol.” Claim 20 recites the same phrase. The phrase is unclear because an ammonium alcohol is not an “amine” in the same sense as an aminic alcohol. It is unclear whether the claimed molar ratio is based on the total amount of aminic alcohol or ammonium alcohol, the amount of nitrogen-containing compound, the amount of amine precursor used to form an ammonium salt, or only free amine functionality. As written, the metes and bounds of the claimed molar ratio cannot be determined with reasonable certainty.
Claims 21-23 recite that “the 2,3-epoxy-1-propanol has a molecular weight” within the stated ranges. This language renders the claims indefinite because 2,3-epoxy-1-propanol is recited in claim 15 as a reactant, while the stated molecular-weight ranges correspond to the disclosed linear or branched polyhydroxyl, not the 2,3-epoxy-1-propanol reactant. It is therefore unclear whether the claims are intended to limit the 2,3-epoxy-1-propanol reactant or the resulting linear or branched polyhydroxyl. The scope of claims 21-23 is not reasonably certain.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached at 572-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691
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