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 .
Election/Restrictions
Claims 19-20 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 30 June 2026.
The arguments pertaining to the election of species were convincing and the election of species restriction has been withdrawn. Claims 1-18 will be examined.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1–7 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Umemoto, US 2003/0148188 (“Umemoto”).
Umemoto discloses a genus of silylamines and expressly identifies individual N,N-bis(trimethylsilyl)-substituted amines. Paragraph [0088] identifies, inter alia, N,N-bis(trimethylsilyl)methylamine, ethylamine, propylamine, isopropylamine, butylamine, cyclopentylamine, cyclohexylamine, and N,N-bis(trimethylsilyl)aniline. Umemoto further states that the silylamines are commercially available or readily prepared according to techniques known in the art. See Umemoto ¶ [0088].
Claim 1 is anticipated by Umemoto because N,N-bis(trimethylsilyl)methylamine falls within the claimed precursor formula. In that expressly disclosed compound, R¹ is methyl, an alkyl, and R²–R⁷ are methyl because nitrogen is bonded to two trimethylsilyl groups. Methyl is within the alternatives expressly permitted for each of R¹–R⁷ by claim 1. Umemoto ¶ [0088].
Claim 2 is anticipated because Umemoto expressly identifies N,N-bis(trimethylsilyl)methylamine, ethylamine, propylamine, isopropylamine, butylamine, and additional N-alkyl species, each having R¹ equal to an alkyl group. Umemoto ¶ [0088].
Claim 3 is anticipated because the expressly disclosed methyl, ethyl, propyl, and butyl N,N-bis(trimethylsilyl)amines provide species wherein R¹ is a linear C1–C4 alkyl. Umemoto ¶ [0088]. Claim 4 is anticipated because Umemoto expressly discloses N,N-bis(trimethylsilyl)isopropylamine. Isopropyl is a branched C3 alkyl falling within the recited branched C3–C4 alkyl limitation. Umemoto ¶ [0088].
Claim 5 is anticipated because Umemoto expressly discloses N,N-bis(trimethylsilyl)cyclopentylamine and N,N-bis(trimethylsilyl)cyclohexylamine. Each provides a precursor wherein R¹ is cycloalkyl. Umemoto ¶ [0088].
Claim 6 is anticipated for the same reason. Cyclopentyl and cyclohexyl are C5 and C6 cycloalkyl groups, respectively, and therefore fall expressly within the claimed C3–C6 cycloalkyl genus. Umemoto ¶ [0088].
Claim 7 is anticipated because Umemoto expressly identifies N,N-bis(trimethylsilyl)aniline. The nitrogen substituent in that compound is phenyl, which satisfies R¹ = aryl. Umemoto ¶ [0088].
Claim 9 is anticipated because the N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-cyclopentyl, N-cyclohexyl, and N-phenyl substituents expressly disclosed by Umemoto do not comprise silicon. Accordingly, the disclosed species relied upon above also satisfy the additional limitation that R¹ does not comprise silicon. Umemoto ¶ [0088].
The fact that Umemoto employs the disclosed silylamines for a different ultimate purpose does not distinguish claims 1–7 or 9 because those claims are directed to the compounds themselves and do not require a particular end use.
Claim 8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bou-Moreno, (“Bou-Moreno”).
Claim 8 requires the precursor of claim 1 wherein R¹ is benzyl. Bou-Moreno expressly prepares and identifies N,N-bis(trimethylsilyl)benzylamine. Specifically, Bou-Moreno reports reacting N-trimethylsilylbenzylamine with n-butyllithium and trimethylchlorosilane to obtain N,N-bis(trimethylsilyl)benzylamine in 60% yield and provides ^1H and ^13C NMR characterization of the resulting compound. See Bou-Moreno, pp. 196–197, lines 8270–8277.
In the expressly disclosed compound, R¹ is benzyl and R²–R⁷ are methyl. Accordingly, every structural limitation of claims 1 and 8 is expressly met.
Claim 10 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Gundersen (“Gundersen”).
Claim 10 recites that the precursor comprises at least one of a series of specifically depicted compounds. The first depicted species includes N-methylbis(dimethylsilyl)amine.
Gundersen expressly identifies and structurally characterizes bis(dimethylsilyl)methylamine, NMe(SiHMe₂)₂, in the gas phase. The reference reports the molecular structure and bond parameters of that compound. See Gundersen, Abstract, p. 191. NMe(SiHMe₂)₂ corresponds to the specifically depicted N-methylbis(dimethylsilyl)amine species of claim 10. Because claim 10 is written in the alternative as comprising “at least one of” the depicted compounds, disclosure of one of the recited species anticipates the claim.
Claims 11–16 and 18 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by JPH08-134078A, published May 28, 1996 (“JP ’078”).
JP ’078 teaches reacting an amino compound of formula R–NH₂ with trimethylchlorosilane in the presence of a tertiary amine and Lewis-acid catalyst to form an N,N-bis(trimethylsilyl)amine. JP ’078 ¶¶ [0005]–[0006]. The reference defines R to include alkyl, alkenyl, alkynyl, aralkyl, and pyridylalkyl groups and specifically identifies methyl, ethyl, propyl, n-butyl, allyl, propargyl, benzyl, and phenethyl, among others. See ¶ [0007].
Claim 11 is anticipated because JP ’078 expressly teaches obtaining a primary amine and trimethylchlorosilane and reacting those materials to form an N,N-bis(trimethylsilyl)amine. See ¶¶ [0005]–[0007]. Example 1 specifically charges trimethylchlorosilane and adds allylamine to form N,N-bis(trimethylsilyl)allylamine. See ¶ [0016].
For the product of Example 1, R¹ is allyl, an alkenyl group, and R²–R⁷ are methyl. Thus, each substituent falls within the alternatives expressly recited in claim 11.
Claim 12 is anticipated because JP ’078 expressly defines its starting amino compound as R–NH₂. Paragraph [0007] identifies, among others, methyl, ethyl, propyl, n-butyl, allyl, propargyl, benzyl, and phenethyl groups for R. Example 1 specifically employs allylamine. JP ’078 ¶¶ [0006]–[0007], [0016].
Claim 13 is anticipated because JP ’078 expressly employs trimethylchlorosilane. Trimethylchlorosilane has the formula R²R³R⁴Si–X₁ wherein X₁ is Cl and R², R³, and R⁴ are each methyl, satisfying the formula of claim 13. See ¶¶ [0005]–[0006] and Example 1, ¶ [0016].
Claim 14 is anticipated because the same trimethylchlorosilane satisfies R⁵R⁶R⁷Si–X₂ wherein X₂ is Cl and R⁵, R⁶, and R⁷ are each methyl. Claim 14 does not require the silylhalide satisfying its formula to be chemically different from the silylhalide of claim 13.
Claims 15 and 16 are interpreted for purposes of prior-art examination consistently with the specification's apparent intended use of the ratio terminology, while the separate §112(b) rejection is maintained. The specification characterizes “at least 1:1” as encompassing ratios extending from 1:1 through 1:10.
Claim 15 is anticipated because JP ’078 teaches using two moles of trimethylchlorosilane per mole of amino compound and states that this 2:1 silylhalide-to-amine stoichiometry is economically preferable. JP ’078 ¶ [0009]. Example 1 uses 10 mmol allylamine and 22 mmol trimethylchlorosilane, corresponding to an amine:silylhalide ratio of approximately 1:2.2. JP ’078 ¶ [0016]. This falls within claim 15 under the interpretation indicated by Applicant's specification.
Claim 16 is likewise anticipated because JP ’078 expressly teaches two molar equivalents of trimethylchlorosilane per mole of amino compound. See ¶ [0009]. Example 1 employs approximately 2.2 equivalents of trimethylchlorosilane per equivalent of allylamine. See ¶ [0016]. Thus, the reference expressly meets the disclosed intended scope of the “at least 1:2” limitation.
Claim 18 is anticipated because JP ’078 teaches that the same amine/silylhalide reaction may be conducted in an aprotic solvent and expressly identifies hexane among suitable solvents. See ¶ [0013]. Claim 18 expressly recites n-hexane as one of the permitted solvents.
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 1-9 and 11-18 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.
Independent claim 1 is directed to a genus of disilylamine precursor compounds wherein R¹ may be alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl, and each of R²–R⁷ independently may be hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl. Thus, the claim permits independent variation at seven substituent positions over multiple broad structural classes.
Claims 2–8 limit only R¹. Claims 2–4 respectively require R¹ to be alkyl, linear C1–C4 alkyl, or branched C3–C4 alkyl; claims 5–8 respectively require R¹ to be cycloalkyl, C3–C6 cycloalkyl, aryl, or benzyl. Claim 9 requires that R¹ not comprise silicon. These limitations narrow the substituent attached to nitrogen but leave each of R²–R⁷ independently selectable from the broad classes recited in claim 1. Accordingly, claims 2–9 continue to encompass a substantial number of structurally different disilylamine compounds.
Independent claim 11 similarly encompasses formation of a precursor having the same broadly variable R¹–R⁷ substituent pattern. Claim 12 specifies the primary amine starting material; claims 13 and 14 specify broad first and second silylhalide structures; claims 15 and 16 recite molar ratios; claim 17 recites sequential formation through a monosilylated intermediate; and claim 18 specifies solvents. None of these dependent limitations materially limits the breadth of the final R¹–R⁷ precursor genus.
The specification provides the generic precursor formula and expressly identifies the same R¹–R⁷ substituent alternatives recited in the claims. The specification further teaches obtaining an amine and at least one silylhalide and contacting those materials to form the precursor, and provides corresponding generic amine and silylhalide structures. The disclosure also provides a sequential first- and second-silylation route and identifies the claimed monosilylated intermediate. Suitable solvents and broad reaction conditions are likewise disclosed.
The working examples, however, occupy a considerably narrower portion of the claimed genus. The examples prepare bis(dimethylsilyl)cyclohexylamine, bis(dimethylsilyl)(tert-butyl)amine, bis(dimethylsilyl)(isopropyl)amine, and N-ethylbis(dimethylsilyl)amine. Thus, although the examples provide representative variation at R¹, they principally employ the same dimethylsilyl substitution pattern and do not demonstrate preparation across the broad independent variation permitted at R²–R⁷.
The question is not whether the disclosure enables the particular exemplified compounds. Rather, the question is whether the disclosure enables a person of ordinary skill to make the full scope of claims 1–9 and 11–18 without undue experimentation.
The Wands factors are considered as follows.
(1) Breadth of the claims. This factor weighs against enablement. Claim 1 permits R¹ to be selected from six broad substituent classes and permits each of R²–R⁷ independently to be hydrogen or one of those broad substituent classes. The resulting genus is substantially broader than the particular dimethylsilyl compounds demonstrated in the working examples. Claims 2–9 narrow R¹ but leave the six silicon substituent positions broadly variable. Claim 11 carries essentially the same chemical breadth into the method claims.
(2) Nature of the invention. The claimed invention concerns preparation of substituted disilylamine compounds by silylation of amines. Whether a particular disilylamine is formed, remains sufficiently stable, can be isolated, and can be purified depends upon the structures of the selected amine and silylhalide reactants. The claims are not confined to the specific dimethylsilyl reactants shown to operate in the examples.
(3) State of the prior art. This factor weighs in Applicant's favor to a degree. Amine silylation and disilylamine chemistry were known, and a person of ordinary skill would have been familiar with conventional silylation reactions, bases, solvents, purification, and characterization techniques. The existence of known silylation chemistry, however, does not establish that the disclosed procedures are generally applicable without significant experimentation to every combination encompassed by the independently variable R¹–R⁷ definitions.
(4) Level of ordinary skill in the art. This factor weighs in Applicant's favor. A person of ordinary skill would be expected to have substantial training and experience in synthetic organosilicon chemistry and would understand conventional methods for conducting and optimizing amine-silylation reactions.
(5) Predictability of the art. This factor weighs against enablement of the full claimed scope. The disclosure does not establish a predictable correlation showing that replacement of the exemplified methyl substituents on silicon with the full range of claimed alkenyl, alkynyl, cycloalkyl, aryl, benzyl, hydrogen, and alkyl substituents will result in successful precursor formation using the disclosed procedures. Nor does the disclosure establish that the effects of simultaneous changes at multiple R²–R⁷ positions can be predicted from the exemplified dimethylsilyl compounds.
(6) Amount of direction or guidance provided. This factor weighs partly in Applicant's favor. The specification provides generic reactant formulas, stoichiometric guidance, solvents, temperature ranges, and both direct and sequential synthetic routes. For example, the disclosure expressly teaches contacting an amine with one or more silylhalides and, in some embodiments, forming an intermediate with a first silylhalide followed by reaction with a second silylhalide. However, the specification does not identify which portions of the broad R²–R⁷ genus are expected to react successfully under the disclosed conditions, what substitutions require materially different conditions, or what structural limits govern successful formation and isolation of the claimed compounds.
(7) Existence of working examples. This factor weighs in Applicant's favor as to the particular exemplified compounds. Four working syntheses are provided. However, those examples occupy a relatively narrow structural portion of the claimed genus and principally demonstrate variation of R¹ while retaining closely related dimethylsilyl substituents. A few working examples do not, by themselves, enable a substantially broader genus unless the disclosure provides a general principle permitting the skilled artisan reasonably to extrapolate those examples throughout the scope claimed. MPEP § 2164.02 expressly recognizes that the examiner must explain why extrapolation across the entire scope would not reasonably be expected. (USPTO)
(8) Quantity of experimentation required. This factor weighs against enablement. To practice the claims throughout their scope, the skilled artisan would have to select among numerous structurally different amines and silylhalides, determine whether each reaction produces the intended mono- or bis-silylated material, determine suitable stoichiometry, solvent, base, temperature and reaction sequence, determine product stability and isolability, and characterize the resulting compound. Because the specification does not disclose a general structure-reactivity relationship establishing which R²–R⁷ combinations will function according to the disclosed procedures, this experimentation would amount to more than merely following a disclosed routine across the full scope claimed.
Considered together, the Wands factors establish a reasonable basis for concluding that the scope of enablement is not commensurate with the scope of claims 1–9 and 11–18. The rejection is not based merely on the numerical breadth of the genus or the limited number of working examples. Rather, the rejection is based on the combination of the extensive independent structural variation permitted by the claims, the concentration of the actual examples in a narrow dimethylsilyl portion of that genus, the absence of a disclosed principle permitting reliable extrapolation to the remaining R²–R⁷ combinations, and the amount of compound-by-compound experimentation that would be required to determine whether the claimed subject matter can be made throughout its scope.
The disclosure is considered enabling at least for the specifically demonstrated dimethylsilyl precursor compounds and closely related subject matter for which the disclosed synthetic conditions provide adequate guidance.
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 15-16 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 recites that “a molar ratio of the amine compound to the at least one silylhalide compound is at least 1:1.” Claim 16 similarly recites that “a molar ratio of the amine compound to the at least one silylhalide compound is at least 1:2.”
It is unclear what range is established by the term “at least” when applied to the recited amine:silylhalide ratios.
When expressed mathematically as an amine:silylhalide ratio, “at least 1:1” would ordinarily indicate that the quotient of amine to silylhalide is equal to or greater than 1. Under that interpretation, 2:1 would satisfy the limitation while 1:2 would not.
The specification, however, states that the molar ratio of amine compound to silylhalide compound is “at least 1:1” and thereafter describes that ratio as ranging from 1:1 to 1:10, including 1:2, 1:3, 1:4, and progressively larger amounts of silylhalide relative to amine. The disclosure therefore appears to use “at least” to refer to the amount of silylhalide relative to a fixed amount of amine rather than to the numerical value of the expressly stated amine:silylhalide ratio.
Claim 16 presents the same ambiguity. It is unclear whether “at least 1:2” encompasses all numerical amine:silylhalide ratios equal to or greater than 0.5, including 1:1 and 2:1, or whether Applicant intends the limitation to require at least two moles of silylhalide for each mole of amine, such as 1:2, 1:3, 1:4, and so forth.
Accordingly, the metes and bounds of claims 15 and 16 cannot be determined with reasonable certainty.
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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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691
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