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 .
DETAILED ACTION
Claims 1-15 of W. Knott, et al., US 18/447,527 (08/10/2023) are pending. Claims 10-12 are withdrawn. Claims 1-9 and 13-15 are under examination on merits and are rejected.
Specification
The abstract of the disclosure is objected to because exceeds 150 word. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Priority
Acknowledgment is made of applicant's claim for foreign priority based on an application filed in EP on 08/12/2022. It is noted, however, that applicant has not filed a certified copy of the EP22190104.4 application as required by 37 CFR 1.55
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I (claims 1-9 and 13-15), with traverse, in the reply filed on 02/17/2026. Claims 10-12 drawn to non-elected Group (II)-(III) are withdrawn from consideration pursuant to 37 CFR 1.142(b).
Applicant’s Restriction Traversal
Applicant first traverses the Restriction between Group I and Group II on the ground that:
there is no evidence of record to show that the claimed products could be made as the Office has alleged. If, in fact, the claimed product can be made by a reaction of an alcohol with a hydrosiloxane in the presence of a palladium or platinum catalyst, the Office has failed to show that the alleged process is materially different from the claimed process.
This argument is not persuasive because as discussed in the previous office action that Rathore teaches that alkoxysiloxanes can be prepared through a reaction of reaction of an alcohol with a hydrosiloxane in the presence of a palladium or platinum catalyst. See J. S. Rathore, et al, WO2014099497A2 (2014)(“Rathore”) at Abstract . Given the Rathore method using a palladium or platinum as a catalyst rather the claimed alkali metal alkoxide, the Rathore method is materially different from the claimed process.
Applicant then argues the Restriction between Group I and Group III on the ground that Examiner does not provide evidence to show the processes claimed by Group I and Group III are materially different. This argument is not persuasive because the Group I is directed to a process for producing alkoxysiloxanes by thermal reaction of at least one siloxane parent structure with at least one alkali metal alkoxide and at least one alcohol , while the Group III is directed to a process for producing SiOC-bonded polyether siloxanes, by transesterification of the alkoxysiloxanes formed with the process according to Group (I) with polyetherols in the presence of a zinc acetylacetonate as catalyst. As mentioned in the previous Office action that the claimed processes have a materially different design and do not overlap in scope, therefore, they are distinct.
Applicant further argues the Restriction between Group II and Group III on the ground that Examiner does not establish the claimed product can be use different process. This argument is not persuasive, as mentioned in the previous Office action that Rathore teaches that alkoxysiloxanes can be used for making thin-inorganic films. See J. S. Rathore, et al, WO2014099497A2 (2014)(“Rathore”) at page 4, line 1-2. Given forming a thin-film has a different subject matter as the claimed for forming a SiOC-bonded polyether siloxanes, therefore, Inventions II and III are distinct.
Overall, the Restriction Requirement mailed on 12/16/2025 is proper and is made as Final.
Claim Rejections - 35 USC § 112(b)
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Claims 1-9 and 13-15 are rejected under 35 U.S.C. 112(b) as indefinite. The independent claim 1 recites the limitation of
Wherein the at least one siloxane parent structure is selected from the group consisting of hexamethylcyclotrisiloxane (D3), octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), mixtures of cyclic branched siloxanes of a D/T type, silicone oils, polydimethylsiloxanediols and α,ω-divinyl siloxanes.
The specification does not provide definition for the claimed “silicone oils”, Examiner conducted keyword searching with Google and do not find a clear structure definition for “silicone oils” in prior arts.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 9 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 9 is depending on claim 1 which limits the claimed at least one siloxane parent structure as
selected from the group consisting of hexamethylcyclotrisiloxane (D3), octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), mixtures of cyclic branched siloxanes of a D/T type, silicone oils, polydimethylsiloxanediols and α,ω-divinyl siloxanes.
None of these cited alternative comprise α,ω-dimethoxypolydimethylsiloxane or α,ω- diethoxypolydimethylsiloxane as further limited by claim 9, therefore, claim 9 cannot further limit the subject matter of claim 1, rather it extends the scope of claim 1.
Claim Rejections - 35 USC § 102
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-4, 8 and 13-14 are rejected under 35 U.S.C. 102 (a)(1)(a)(2) as being anticipated by M. Prasse, US20210171716A1 (2021)(“Prasse”)
Prasse teaches a method for producing branched organopolysiloxanes, comprising:
a first step, wherein, at least one alkoxysilane is equilibrated with at least one polydiorganosiloxane in the presence of a basic catalyst, optionally mixed with alcohol, and
a second step, wherein, the equilibrate obtained in the first step is hydrolyzed and condensed with water and optionally other organosilicon compounds in the presence of an acidic catalyst and optionally alcohol.
Prasse at page 1, [0006].
Prasse teaches working example of his method, such as Example 2 as follows:
EXAMPLE 2
[0184] In a 21 glass flask equipped with reflux condenser, dropping funnel and KPG stirrer, 260 g of methyltrimethoxysilane, 576 g of phenyltriethoxysilane, 72g of dihydroxy-terminated polydimethylsiloxane having a viscosity of 80 mPas and 1.0 g (4.6 mmol) of sodium methoxide solution (25% in methanol) are stirred at 100° C. for one hour, then acidified with 2.4 g of hydrochloric acid (20%), 95 g of water are added over the course of 15 minutes and the mixture is stirred at reflux for one hour.
[0185] The condensed, HCl-acidic end product thus obtained is neutralized with a sodium methoxide solution (25% in methanol) and subsequently filtered.
[0186] Subsequently, to the alcoholic end product solution is added 200 g of a solid phenyl resin, commercially available from WACKER Chemie AG under the name SILRES® 604, the mixture distilled and a liquid and clear end product is obtained which is defined by viscosity, alkoxy radical content and molecular weight distribution as follows:
[0187] Molecular composition by 29Si-NMR:
[0188] Me2SiO2/2: 14.4 mol %
[0189] Me2Si(OEt)O1/2: 1.4 mol %
[0190] MeSi(OEt)2O1/2: 0.8 mol %,
[0191] MeSi(OEt)O2/2: 14.3 mol %,
[0192] MeSiO3/2+PhSiO1/2: 24.2 mol %,
[0193] PhSi(OEt)O2/2: 31.0 mol %,
[0194] PhSiO3/2: 13.9 mol %,
. . . .
Prasse at page 6-7, [0184]-[0205], Example 2, emphasis added.
The Prasse process comprises:
(i).mixing a mixture comprising dihydroxy-terminated polydimethylsiloxane, sodium methoxide and methanol at 100° C. for one hour; wherein, no water is removed from the reaction mixture, and the reaction mixture does not comprise solvents which form an azeotrope with water and without the use of further dehydrating agents;
(ii).neutralizing the reaction mixture by addition of hydrochloric acid that is a Bronsted acid;
(iii).distillation of the alkoxysiloxane products Me2Si(OEt)O1/2, MeSi(OEt)2O1/2, MeSi(OEt)O2/2, PhSi(OEt)O2/2.
which meets each and every limitation of claim 1, therefore, claim 1 is anticipated.
Claims 2 and 14 are anticipated because sodium methoxide (NaOMe) is used in the Prasse process.
Claim 3 is anticipate because methanol used in the Prasse process is a linear alkanol having one carbon atom.
Claim 4 is anticipated because the step 1 of the Prasse process is conducted at 100° C. for one hour.
Claim 8 is anticipated because the at least one solvent in step b of claim 1 is an optional.
Claim 13 is anticipated because there is a step of filtration of solid after neutralization in the Prasse process.
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.
Claims 5-7, 9 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over M. Prasse, US20210171716A1 (2021)(“Prasse”) as applied above for the rejection of claim 1.
M. Prasse, US20210171716A1 (2021)(“Prasse”)
As mentioned above that Prasse teaches a method for producing branched organopolysiloxanes, comprising:
a first step, wherein, at least one alkoxysilane is equilibrated with at least one polydiorganosiloxane in the presence of a basic catalyst, optionally mixed with alcohol, and
a second step, wherein, the equilibrate obtained in the first step is hydrolyzed and condensed with water and optionally other organosilicon compounds in the presence of an acidic catalyst and optionally alcohol.
Prasse at page 1, [0006].
Regarding the polydiorganosiloxane, Prasse teaches that:
[0033] The polydiorganosiloxanes used in accordance with the invention are preferably linear or cyclic siloxanes consisting of units of the formula
Rc(OR2)dSiO4-c-d/2 (III),
Where,
R has the definition specified above,
R2 may be the same or different and is a hydrogen atom or a hydrocarbon radical having 1 to 4 carbon atoms,
c is equal to 2 or 3 and
d is equal to 0 or 1,
with the proviso that the sum of c+d≤3 and c has the value 2 in at least 50%, preferably in at least 70%, particularly preferably in at least 90%, of all units of the formula (I).
Prasse at page 2, left col. [0033].
Regarding the amount of the basic catalyst and alcohol, Prasse teaches that:
In the process according to the invention, preference is given to using basic catalysts in amounts from 50 to 5,000 ppm by weight, particularly preferably 100 to 2,500 ppm by weight, based in each case on the total weight of silanes of the formula (II) and organopolysiloxanes composed of units of the formula (III).
. . . .
[0049] In the first step of the process according to the invention, alcohol is preferably used in amounts from 0 to 20% by weight, based in each case on the total weight of silanes of the formula (II) and organopolysiloxanes composed of units of the formula (III). If alcohol is used in the first process step, it is preferably used as the solvent for the basic catalyst and/or an impurity in the silanes used.
Prasse at page 2,right col. [0046] and [0049], emphasis added. Thus, Prasse teaches that both the amount basic catalysts and the amount of alcohol are factors that can be optimized.
Regarding the acidic catalyst, Prasse teaches that:
[0059] Examples of acidic catalysts used in accordance with the invention are inorganic acids such as hydrochloric acid, hydrofluoric acid, sulfuric acid, nitric acid, perchloric acid or phosphoric acid, sulfonic acids such as trifluoromethanesulfonic acid, fluorosulfonic acid or methylsulfonic acid, phosphoric acids such as vinylphosphonic acid or n-octylphosphonic acid, organic acids such as trifluoroacetic acid, formic acid, oxalic acid or n-octanoic acid . . . .
Prasse at page 3, [0059], emphasis added.
As detail discussed in the 102 rejection above that Prasse teaches working example 2 that meets each and every limitation of claim 1.
Difference between Prasse example 2 and Claims 5-7, 9 and 15
The Prasse example 2 process differs claims 5-6 in that the concentrations of sodium methoxide and methanol in the Prasse example 2 process does not meet the claimed concentrations.
The Prasse example 2 process differs claims 7 and 15 in that 20% HCl used in the Prasse example 2 process is not anhydrous acid or the anhydrous acids listed in claim 15.
The Prasse example 2 process differs claim 9 in that the dihydroxy-terminated polydimethylsiloxane used in the Prasse example 2 process is a α,ω-hydroxylpolydimethylsiloxane rather the claimed α,ω-dimethoxypolydimethylsiloxane.
Claims 5-7 and 15 are Obvious
Claims 5-6 are obvious because one ordinary skill seeking branched organopolysiloxanes is motivated to optimize the Prasse example 2 process by adjusting concentration of sodium methoxide and/or methanol into the claimed ranges because Prasse teaches that both the amount basic catalysts (such as sodium methoxide) and the amount of alcohol (such as methanol) for his method are factors that needs to be optimized. Generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such range is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). Herein, neither prior art nor the specification provides evidence to show the claimed concentrations of the alkali metal alkoxide and/or the at least one alcohol is critical, rather the specification discloses that:
It is preferable when the at least one alkali metal alkoxide is employed in total amounts of 1% to 10% by mass, preferably of 2% to 7% by mass, particularly preferably of 3% to 6% by mass, based on the total amount of the at least one siloxane parent structure.
Specification at page 8, line 1-5.
It is preferable when the at least one alcohol is employed in total amounts of 10% to 200% by mass, preferably of 20% to 100% by mass, particularly preferably in amounts of 30% to 80% by mass, based on the total mass of the at least one siloxane parent structure.
Specification at page 8, line 13-15.
Claims 7 and 15 are obvious because one ordinary skill seeking branched organopolysiloxanes is also motivated to optimize the Prasse example 2 process by replacing of 20% HCl with anhydrous perchloric acid because Prasse teaches that perchloric acid can be used as an acid to neutralize the basic catalyst.
Claim 9 is also obvious because one ordinary skill seeking branched organopolysiloxanes is also motivated to modify the Prasse example 2 process by replacing of the α,ω-hydroxylpolydimethylsiloxane (one species of the polydiorganosiloxanes formula III) with α,ω-dimethoxypolydimethylsiloxane(another species of the polydiorganosiloxanes formula III) because Prasse teaches that hydroxy groups in the polydiorganosiloxanes formula III can be replaced by C1-C4 alkoxyl group. Prasse at page 2, left col. [0033].
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
Claims 1-4, 7 and 13-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2, 5, 10-11, 19 and 23 of co-pending Application No. 18/447,540 (published as US20240052132A1) in the claim set filed on 08/10/2023. This is a provisional nonstatutory double patenting rejection.
Regarding claims 1 and 13, the conflicting claim 1 claims:
A process for producing one or more alkoxysiloxanes by a thermal reaction of at least one waste silicone with at least one alkali metal alkoxide and at least one alcohol,
wherein the process comprises:
(a) reacting the at least one waste silicone by mixing with at least one alcohol and at least one alkali metal alkoxide with heating but without removing any potentially occurring water from the reaction mixture, and
(b) neutralizing the reaction mixture resulting from the reacting by neutralization with at least one Brønsted acid, and optionally with an addition of at least one solvent, and separating by filtration the solid constituents, and
(c) subsequently isolating the alkoxysilane(s) by thermal separation of volatile compounds.
The conflicting claim 2 further claims:
The process according claim 1,
wherein in the reacting at least one additional siloxane is selected from the group consisting of hexamethylcyclotrisiloxane (D3), octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), dodecamethylcyclohexasiloxane (D6), mixtures of cyclic branched siloxanes of the D/T type, silicone oils, polydimethylsiloxane diols and α,ω-divinylsiloxanes is added.
The conflicting claim 2 meets each and every limitation of claims 1 and 13, therefore, claims 1 and 13 are anticipated.
Regarding claims 2 and 14, the conflicting claim 19 claims:
The process according to claim 1,
wherein the at least one alkali metal alkoxide conforms to the general formula [M+] [OR−],
wherein
M is selected from the group of alkali metals Na or K, and
R represents a linear, branched or cyclic alkyl radical having 1 to 10 carbon atoms.
Thus, the combination of the conflicting claims 2 and 19 meets each and every limitations of claims 2 and 14, therefore, claims 2 and 14 are obvious.
Regarding claim 3, the conflicting claim 5 claims:
The process according to claim 1,
wherein the at least one alcohol employed in the reacting is selected from the group consisting of linear, branched and cyclic C1 to C10 alkanols, and an isomer relevant thereof to the selected group is included.
Thus, the combination of the conflicting claims 2 and 5 meets each and every limitations of claim 3, therefore, claim 3 is obvious.
Regarding claim 4, the conflicting claims 10-11 claims:
10.The process according to claim 1,
wherein the thermal reaction of the at least one waste silicone in the reacting is undertaken at temperatures between 50° C. and 200° C.
11, The process according to claim 1,
wherein the thermal reaction of the at least one waste silicone in the reacting is performed over a period of 1 to 12 hours.
Thus, the combination of the conflicting claims 2 and 10-11 meets each and every limitations of claim 4, therefore, claim 4 is obvious.
Regarding claims 7 and 15, the conflicting claim 23 claims:
The process according to claim 1,
wherein the at least one Brønsted acid added in the neutralizing is anhydrous mineral acid and/or anhydrous organic acid, selected from the group of anhydrous sulfuric acid, anhydrous perchloric acid and/or anhydrous acetic acid.
Thus, the combination of the conflicting claims 2 and 23 meets each and every limitations of claims 7 and 15, therefore, claims 7 and 15 are obvious.
Terminal Disclaimer
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. (FP 7.96) Hass et al (US 20250136625A1) teaches a method for preparing organic silicon compounds through reacting at least one alkoxy alkyl silane of the formula (Ia) and/or a cyclic siloxane of the formula (Ib) with at least one alkoxy alkanol of the formula (II). The reaction occurs in the presence of at least one acid or at least one base, optionally in a solvent, at a temperature of 0 to 200°C.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692