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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 14 objected to because of the following informalities: the claim should read "obtained by the process of claim 1."
Claim 13 is objected to because there is an extra “e” in dieethoxypolydimethylsiloxane, it should read diethoxypolydimethylsiloxane.
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.
Claims 1-16 are 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.
Regarding claims 1 and 12, the phrase "preferably" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claims 2-16 are also rejected under 112b due to their dependency on claim 1.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 17 and 18 recite the broad recitation silicic esters, and the claims also recite tetraalkoxysiloxanes which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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.
Claims 1-3, 9, 11, 14-15, 17-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Martin et al, US3878263A.
Regarding claims 1, 3, 11, 14 and 19, Martin teaches a process for producing acrylate functional polysiloxane polymers which also have alkoxy groups, abstract. Martin specifically teaches the process in example 1, Col. 7 lines 45-58, where hexamethylcyclotrisiloxane is reacted with methacrylatopropyltrimethoxysilane in benzene and ethylene glycol dimethylether in the presence of n-butyl lithium catalyst. Although Martin uses the n-butyl lithium in the examples, lithium alkoxides are also listed as suitable catalysts, with lithium methoxide shown in the reaction formula, Col. 5 line 55 and reaction 2, therefore the skilled artisan would immediately envisage utilizing a lithium alkoxide such as lithium methoxide in the process, which anticipates the metal alkoxide of claims 1, 3, and 19.
The reaction is heated to reflux, no alcohol is added and no water is removed, this step reads on the claimed step a, where the siloxane parent structure is D3. The catalyst is then neutralized with acetic acid, Col. 7 line 54, and the product is filtered, which reads on step b and claim 11. The solvent is then removed by heating to 130°C, Col. 7 line 55, which reads on step c. The resulting product is shown in Col. 8 lines 1-10, where it has a methoxy terminal group and a methoxy pendant group on the siloxane backbone. Martin further teaches in example 4 that D4 is also used to create an acrylate and methoxy functional polysiloxane, Col. 8 lines 55-61. These siloxanes read on the alkoxysiloxane because applicant states on page 1 line 8 of the instant specification that an alkoxysiloxane is a siloxane with one or more alkoxy groups, which also reads on claim 14.
Regarding claim 2, Martin uses benzene as the solvent in the examples 1-5, Col. 7-8, which does not form an azeotrope with water.
Regarding claim 9, Martin teaches in example 1 that the catalyst is 0.2 parts and the D3 is 111 parts, Col. 7 lines 45-46. This calculates to 0.18 wt.% and 99.82 wt.%, Using the molecular weight of lithium methoxide 37.975 g/mol and the molecular weight of D3 of 222.462 g/mol, the moles are 0.00474 mol and 0.44871 mol respectively. Therefore the lithium methoxide is 1.06 mol% based on the amount of D3, which falls within the claimed range.
Regarding claim 15, Martin teaches the polymers are used as reactive intermediates in the formation of various coating compositions, Col. 7 lines 34-38, which reads on the claimed polymerization-active mass.
Regarding claims 17 and 18, Martin does not teach adding silicic esters or tetraalkoxysiloxanes to the reaction. Martin does not add any solvents that form an azeotrope with water.
Claims 14-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Knott et al US20190040205A1.
Regarding claim 14, this is a product by process claim, the patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985).
Knott teaches an alkoxysiloxane of formula (I) ¶[0055], which has terminal alkoxy groups, and Knott specifically teaches an α,ω-diethoxypolydimethylsiloxane used in example 1, ¶[0087], which is the same alkoxysiloxane that applicant makes in example 2 of the instant specification. Knott is silent as to the manufacturing process for the alkoxysiloxane, but because the product is the same, it reads on the claim.
Regarding claims 15-16, Knott teaches a process for producing an SiOC bonded polyether siloxane by transesterifying an alkoxysiloxane with a polyetherol in the presence of zinc acetylacetonate catalyst, abstract and ¶¶[0015, 0087-0088], which reads on claim 16. Furthermore, this polymerization reads on the polymerization-active mass of claim 15. Knott also teaches the finished product is used as an additive in coating systems, ¶¶[0032, 0034], which reads on the polymerization-active mass of claim 15.
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.
Claims 8 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Martin et al, US3878263A.
Regarding claim 8, Martin teaches the process according to claim 1 as explained above. Martin further teaches the reaction is heated to reflux in the examples, but is silent as to the exact temperature. In the broader disclosure, Martin teaches that the reaction is carried out at temperatures ranging from 25°C to about 150°C, Col. 6 lines 64-67, which overlaps with the claimed range. Therefore it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be prima facie obvious. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).
Regarding claim 12, Martin teaches the process according to claim 1 as explained above. Martin adds the reactants with the benzene solvent at the beginning of the reaction and is silent to the addition of solvent with the neutralizing step b, but does not teach away from adding solvent in the neutralizing step. Additionally, Martin teaches alkane and alkylaromatic solvents such as hexane and toluene are suitable for use, Col. 7 lines 25-28. The selection of any order of performing process steps has been held to be prima facie obvious. Therefore it would have been obvious to one having ordinary skill in the art at the time the invention was made to have added the alkane or alkylaromatic solvent during step b. See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) which states that selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.
Claims 1-15, 17-19 are rejected under 35 U.S.C. 103 as being unpatentable over Ostrozynski et al, US3477988A.
Regarding claims 1, 3-4, 6, 11, 14, 19, Ostrozynski teaches a method for preparing organopolysiloxanes by siloxane rearrangement comprising reacting organosiloxane compounds with a base catalyst and a phosphorous promoter, abstract and Col. 6 lines 58-65. In particular it is taught in example 6, Col.14 lines 33-48, a polydimethylsiloxane with terminal ethoxy groups (alkoxysiloxane) is produced from the heated reaction of octamethylcyclotetrasiloxane (D4), dimethyldiethoxysilane, phosphorous promoter, and potassium silanolate catalyst in toluene; this alkoxysiloxane also reads on claim 14. The D4 reads on the claimed siloxane parent structure. It is also taught that various other basic catalysts may be used in the siloxane rearrangements, such as sodium and potassium methoxides and ethoxides, Col. 11 lines 1-4, which reads on step (a) of claim 1 and reads on claims 3, 4, 6, and 19. It is prima facie obvious to substitute one material for another to obtain predictable results when the materials provide the same use and function, in this case as a polymerization catalyst.
Furthermore, when using an alkali metal base catalyst, it is taught that thermally stable siloxane products cannot be produced unless the base is catalyst is chemically neutralized, Col. 3 line 66. Ostrozynski exemplifies neutralizing with acetic acid in example 15, Col. 19 line 47, which reads on the acid of claim 1 step (b) and claim 11. Additionally, there is no alcohol added nor is any water removed in example 6 where the alkoxysiloxane is produced.
Regarding step (c) of claim 1, in example 6 the solutions are heated for 24 hours at 70°C before cooling, Col. 14 line 44, although it is not specified with this example that the product is isolated and volatile are removed, Ostrozynski teaches isolating the product of example 14, Col. 18 lines 72-76 to Col. 19 lines 1-2, the reaction is neutralized with acetic acid, the crude product is washed with water, and then sparged with nitrogen for one hour at 150°C, which isolates the product and would remove any volatiles in the mixture.
It would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the potassium silanolate catalyst with sodium or potassium methoxide or ethoxide, neutralizing with acetic acid, and furthermore isolating the product by washing followed by sparging with nitrogen at 150°C to remove the volatiles with the motivation of obtaining the predictable result of the alkoxy functional polydimethylsiloxane because it is a simple substitution of catalysts and isolating the product as disclosed by Ostrozynski.
Regarding claim 2, Ostrozynski exemplifies toluene in example 6, but also lists other solvents such as xylene and benzene as examples of solvents, Col. 11 line 64, which do not form azeotropes with water.
Regarding claims 5 and 10, Ostrozynski teaches the siloxane rearrangement reactions can be carried out in the presence of silica, Col. 4 lines 65-67, Col. 10 lines 58-65. The pyrogenic silica, Cab-O-Sil MS-5 is exemplified in example 18, Col. 20 lines 55-72. The silica is added with the cyclic dimethylsiloxanes and base catalyst, which is part of the claimed step (a). The pyrogenic silica is pulverulent and it is recommended that 0.1-20 wt.% of filler based on the organopolysiloxane be used, Col. 10 line 73. Considering example 6, which uses D4 with a molecular weight of 296.62 g/mol, used at 73.5 parts, this is 0.248 mol, the amount of pyrogenic silica that can be added is 0.1-20% of 73.5, which is 0.0735-14.7 parts. Silica has a molecular weight of 68 g/mol, converting the parts to moles becomes 0.00108-0.216 mol, which is 0.436-87.24 mol% based on the amount of D4, which encompasses the claimed range. Therefore it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be prima facie obvious. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).
Regarding claim 7, Ostrozynski teaches that solvents can be employed for convenience, but are not necessary and are even not desired in certain instances, such as if the finished product is to be used in a grease, furthermore the phosphorous promoter acts as a solvent, Col. 11 lines 55-61, which means the reaction does not require solvent and can be performed solventlessly.
Regarding claim 8, Ostrozynski teaches the siloxane rearrangements occur within a temperature range of 100-200°C or as low as 25°C, Col. 4 lines 1-5, which encompasses the claimed range. Therefore it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be prima facie obvious. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).
Regarding claim 9, Ostrozynski teaches in example 6 the amount of D4 used is 73.5 parts, with a molecular weight of 296.62 g/mol, this is 0.248 mol. The catalyst is 0.25 parts, which if using sodium methoxide with a molecular weight of 54.02 g/mol, this comes out to 0.00463 mol, which is 1.87 mol% based on the amount of D4. Similarly if potassium methoxide is used instead, it has a molecular weight of 70.13 g/mol, so the amount would be 0.00356 mol, which is 1.44 mol% based on the amount of D4; both of which fall within the claimed range.
Regarding claim 12, Ostrozynski teaches that if solvent is desired, solvents such as toluene and hexane may be used, Col. 11 lines 64-65. Furthermore, in example 6 the solvent is added with the catalyst, Col.14 lines 33-48, but the selection of any order of performing process steps has been held to be prima facie obvious. Therefore it would have been obvious to one having ordinary skill in the art at the time the invention was made to have added the solvent during step (b). See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) which states that selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.
Regarding claims 13 and 15, Ostrozynski teaches the product made in example 6 is ethoxy end capped dimethylpolysiloxane, Col. 14 lines 35-36, which reads on the α,ω-diethoxypolydimethylsiloxane. Furthermore, it is disclosed any alkoxy silane can be present to provide alkoxy end groups, Col. 2 lines 9-11, therefore it would be obvious that the similar product, α,ω-dimethoxypolydimethylsiloxane can also be made by the same process. Additionally, the product made in example 6, α,ω-diethoxypolydimethylsiloxane, reads on the claimed polymerization active mass, because it has reactive groups ready for polymerization and applicant does not require other ingredients with the polymerization active mass. On page 11 lines 4-8 of the instant specification, it states that other ingredients such as catalysts, crosslinkers, and fillers are all optional with the alkoxysiloxane, therefore the product alone reads on the claimed polymerization active mass.
Regarding claims 17-18, Ostrozynski does not teach adding silicic esters or tetraalkoxysiloxanes to the reaction. And further lists other solvents suitable for the reaction such as xylene and benzene, Col. 11 line 64, which do not form an azeotrope with water.
Conclusion
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/V.L.S./Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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