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 .
Status of Claims
Claims 1 – 15 are pending.
Claims 1 – 15 are rejected.
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.
Claims 1- 6 are rejected under 35 U.S.C. 112(b), as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claims 1- 6 are indefinite because the number average molecular weight quoted in instantly claimed 6 appears to be determined by end-group analysis, (see pp. 10, ln 17 – 20 of Applicant’s specification), whereas the polydispersity factor (Mw/Mn) is determined by conventional gel permeation chromatography (GPC) means (see pp. 9, para. 2 of Applicant’s specification).
Claim Rejections - 35 USC § 102/103
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 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.
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.
Claim(s) 1 – 3 and 6 are rejected under 35 U.S.C. 102(a)(1) & (a)(2) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Sunkara et al. (US 6,977,291).
Sunkara describes a method for manufacturing polytrimethylene ether glycol, wherein 1,3-propanediol is subjected to a polycondensation reaction using a polycondensation catalyst at 150 to 210°C and at a pressure less than 50 mmHg (50 torr), such that the content of a cyclic ether is less than 1 wt.%, and further purifying the polytrimethylene ether glycol to a polydispersity of 1.5 to 2.1 (claims 1, 5-7, 13, 25, 32).
Regarding claims 1 and 2, Sunkara discloses polytrimethylene ether glycol with a polydispersity of 1.5 to 2.1. (col. 3, ln 34 - 37; col. 4, ln 49 – 50). The polydispersity (Mw/Mn) was measured by GPC. (col. 8, ln 50- 51).
Regarding claims 1 and 3, Sunkara discloses that polytrimethylene ether glycol has a content cyclic ether oligomers of less than 1%. (col. 3, ln 48 – 50; col. 4, ln 47 – 48).
Regarding claim 6, Sunkara discloses that polytrimethylene ether glycol has number average molecular weight of greater than 1, 500, preferably has a number average molecular weight of from 1,650 to 4,000. (col. 4, ln 46 & ln 52 – 53; Table 2).
Claim Rejections - 35 USC § 102/103
Claim(s) 1 – 6 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Chung et al. (US 2020/0277437 = WO2019/066310).
Chung discloses a polytrimethylene ether glycol having a molecular weight distribution (Mw/Mn) of 1.8 to 2.1, wherein a content of oligomers having a number average molecular weight of 400 or less is 0.5 wt.% or less (claim 1) and wherein a content of 1,3-propanediol is 100 ppm (0.01 wt.%) or less (claim 2). Further disclosing that the cyclic oligomer content is preferably 0.1 wt.% or less [0014]. Also, discloses that the number average molecular weight of said polytrimethylene ether glycol is 400 to 4,000 [0017].
Regarding claims 1 and 2, Chung discloses the polytrimethylene ether glycol has a polydispersity of 1.8 to 2.1 and cyclic oligomer content of 0.1 wt% or less. (pp. 1, [0010] & pp. 2, [0014]).
Regarding claims 1, 3 and 4, Chung discloses that the polytrimethylene ether glycol has cyclic oligomer content of 0.1 wt% or less and a content of oligomers having a number average molecular weight of 400 or less. (pp. 2, [0014]).
Regarding claim 5, , Chung discloses that the polytrimethylene ether glycol has a content of 1,3-propanediol of 100 ppmw or less (converts to 0.01% or less). (pp. 2, [0015]).
Regarding claim 6, Chung discloses that the polytrimethylene ether glycol has number average molecular weight of 400 to 4,000. (pp. 2,[0017]).
Claim Rejections - 35 USC § 103
Claim(s) 7 - 10 are rejected under 35 U.S.C. 103 as being unpatentable over Sunkara et al. (US 6,977,291) in view of Doral et al. (US 5,282,929).
The rejected claims cover, inter alia, a method for preparing the polytrimethylene ether glycol according to claims 1, comprising steps of: polymerizing 1,3-propanediol to prepare a product comprising polytrimethylene ether glycol (step 1); and evaporating the product under conditions of a temperature of 100 to 250°C, and a pressure of 100.0 to 1.0 torr, to remove cyclic oligomer (step 2).
Dependent claims 8 – 10 further limit the temperature and pressure of step 2, the evaporating step.
However, Sunkara discloses a process for the manufacture of polytrimethylene ether comprising the steps of: (a) providing (1) 1,3-propanediol reactant selected from the group consisting of 1,3-propanediol and/or oligomers or prepolymers of 1,3-propanediol having a degree of polymerization of 2-9 and mixtures thereof, and (2) a polycondensation catalyst; and (b) polycondensing the 1,3-propanediol reactant to form a polytrimethylene ether glycol at less than one atmosphere pressure, and the product of the process. In addition, the polytrimethylene glycol has a number average molecular weight greater than 1,500, an APHA color of less than 120, an unsaturation of less than 20 meq/kg, and a content of cyclic ether oligomers of less than 2%. (Abstract). According to Sunkara, the polyether glycol prepared by the process of their invention can be purified. (col. 7, ln 59 – 58).
The difference between Sunkara and the instantly claimed invention is as follows: evaporating the product under conditions of a temperature of 100 to 250°C, and a pressure of 100.0 to 1.0 torr, to remove cyclic oligomer (step 2).
However, Dorai discloses polyether glycols, especially poly(tetramethylene ether) glycol (PTMEG) having a narrow molecular weight distribution of about 1.90 to 2.07, are made by a process wherein the low molecular weight fraction in unit operations using at least one short-path distillation evaporator. In these units, PTMEG is subjected to temperatures in the range of 150-190°C with the hold-up time varying between 10-200 seconds. The required vacuum to force the separation of the low molecular weight PTMEG varies between 0.001 mm and 1.0 mbar. PTMEG residue from the distillation unit is also characterized by its low water content and low concentration of oligomeric cyclic ethers. (Abstract). The type of short path distillation apparatus depicted in the drawings enable the use of very low pressures. In a single stage short path distillation the apparatus evaporative pressures of 0.001 to 1.0 mbar (0.00075 torr to 0.75 torr).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention to modify the process of Sunkara and purify the polytrimethylene ether prepared by their process with apparatus as disclosed in Doral based on the similarity of glycols of Sunkara and Doral. Motivation can be found a desire to produce a is more desirable product, for example because it is stronger, cheaper, cleaner, faster, lighter, smaller, more durable, or more efficient. Because the desire to enhance commercial opportunities by improving a product or process is universal-and even common-sensical, we have held that there exists in these situations a motivation to combine prior art references even absent any hint of suggestion in the references themselves. (DyStar Textilfarben GmbH & Co. Deutschland KG v. C.H. Patrick Co., 464 F.3d 1356, 1366, 1368; 80 USPQ2d 1641, 1649, 1651 (Fed. Cir. 2006)).
Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Claim Rejections - 35 USC § 103
Claim(s) 11 – 15 are rejected under 35 U.S.C. 103 as being unpatentable over Chung et al. (US 2020/0277437 = WO2019/066310).
The Examiner combined the rejection for claims 11 - 15 because the prior art of Chung is applicable to all claim sets, and the invention of claims 11 - 15 are not patentability unobvious from each other.
The rejected claims cover, inter alia, a method for preparing the polytrimethylene ether glycol according to claim 2, 3, 4, 5 or 6, comprising steps of: polymerizing 1,3-propanediol to prepare a product comprising polytrimethylene ether glycol (step 1); and evaporating the product under conditions of a temperature of 100 to 250°C, and a pressure of 100.0 to 1.0 torr, to remove cyclic oligomer (step 2).
Chung also discloses a method of preparing said polytrimethylene ether glycol, the method comprising the steps of preparing a product comprising polytrimethylene ether glycol by polymerizing 1,3-propanediol (Step 1) and preparing purified polytrimethylene ether glycol by distilling the product under conditions of a temperature of 160°C. to 220°C. and a pressure of 0.001 torr to 2.0 torr (Step 2) (claims 5-6). Also, Chung discloses that the number average molecular weight of said polytrimethylene ether glycol is 400 to 4,000 [0017].
According to Chung, a method of purifying polytrimethylene ether glycol without exposing polytrimethylene ether glycol to a high temperature for a long period of time by applying a distillation process as described below. Further, through this method, various by-products and low molecular weight oligomers may be removed, and as a result, the purified polytrimethylene ether glycol may have a narrow molecular weight distribution, thereby reducing the molecular weight variation. (pp. 1, [0013]). The distillation is preferably performed by thin film evaporation. (pp. 2, [0032]). Preferably, the temperature is 160° C. or higher, or 170° C. or higher, and 240° C. or lower, 230° C. or lower, or 220° C. or lower. (pp. 3, [0035]). Preferably, the pressure is 0.005 torr or higher, or 0.01 torr or higher, and 1.5 torr or lower, 1.0 torr or lower, 0.9 torr or lower, 0.8 torr or lower, 0.7 torr or lower, 0.6 torr or lower, 0.5 torr or lower, 0.4 torr or lower, 0.3 torr or lower, 0.2 torr or lower, or 0.1 torr or lower. (pp. 3, [0036]).
The difference between Chung and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Chung teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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