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 .
Specification
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the specification.
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.
Claims 1-17 are rejected under 35 U.S.C. 103 as being unpatentable over Nelson (US 20240093118-appears on the PTO-892).
Nelson teaches a lubricating composition comprising decarboxylated rosin acid (DCR) that may be unhydrogenated or hydrogenated (HDCR) (see abstract; para 0007-0008).
The DCR is a rosin-derived composition obtained by decarboxylating a rosin acid, or by dimerizing and decarboxylating a rosin acid and separating/removing the dimerized species. The DCR is in the form of a liquid. Hydrogenated DCR refers to DCR that has undergone hydrogenation for the reduction of C═C double bonds and obtain hydrogenated compounds (see para 0029).
DCR is produced by the decomposition of rosin acids at high temperatures, e.g., 220-300° C. The rosin acid can be fully decarboxylated forming DCR. The rosin acid can be partially decarboxylated, forming DCR, which is a mixture of molecules, some of which contain monocarboxylic acids having a general molecular formula, e.g., C20H30O2. The DCR comprises one or more C═C groups, 40-100 wt. % of tricyclic species having 18-20 carbon atoms, 0-30 wt. % of components with <19 carbon atoms, and 40-100 wt. % of components with a molecular formula in the range from C19H20 to C19H34, based on the total weight of the DCR. The sum of tricyclic species as aromatic and cycloaliphatic in the DCR is >50 wt. %, or >55 wt. %, or >60 wt. %, or >74 wt. %, or >90 wt. %, or up to 100 wt. %, of total weight of the DCR. Aromatic DCR is defined as DCR species having a MW of 252-256, with MW of 254 as having a reactive double bond, and cycloaliphatic DCR is defined as DCR species having a MW of 260 or 262 (see para 0030-0031).
The DCR has a C19 (MW 248-262) content of >50 wt. %, or >60 wt. %, or >70 wt. %, or >80 wt. %. The amount of cycloaliphatic DCR (MW 260 and 262) is >15 wt. %, based on the total weight of the DCR. The total amount of tricyclic species having reactive double bond (C═C group) is <5 wt. % of total weight of the DCR. Reactive C═C group is defined as DCR species having a MW of 254 or 258. The DCR has C19 species with MWs of 254, 250, and 248 in an amount of <5 wt.; and has a C13 species with MWs of 174 and 180 in an amount of 5-20 wt. % (see para 0032-0035).
After hydrogenation, the amount of tricyclic species having 18-20 carbon atoms in the HDCR goes up to at least 70 wt. based on total weight of the HDCR. After hydrogenation, the HDCR contains C19 species with a MW of 262 in an amount of 25-100 wt.
After hydrogenation, the HDCR contains C19 species with a MW of 260 in an amount of 0-5 wt. %; and contains C19 species with a MW of 256 in an amount of 0-40 wt. %, or 5-35 wt. % (see para 0036-0038).
After hydrogenation, the HDCR contains C19 species with a MW of 252 in an amount of 0-5 wt. % (see para 0040).
After hydrogenation, the HDCR contains C13 species with a MW of 180 in an amount of 0-25 wt. % (see para 0041).
After hydrogenation, the HDCR contains C13 species with a MW of 174 in an amount of 0-5 wt. (see para 0042).
The HDCR comprises at least 5 to 100 isomers of a species having a molecular formula of C19H34 and a MW of 262 g/mol.
After hydrogenation, the HDCR comprises C═C double bonds in amounts of <40% (see para 0045).
After hydrogenation, the HDCR comprises an average Double Bond Equivalent in an amount of 0.1-2 (see para 0046).
DCR is characterized as having an oxygen content 0-2%, or 0-1% (see para 0048).
The HDCR has an acid value of <1 mg KOH/g, as measured using ASTM D1240-14 (2018) or ASTM D465 (see para 0050).
The HDCR has a sulfur content of 0.001-10 ppm, measured according to ASTM D5453 (see para 0063).
The hydrogenated decarboxylated rosin acid has at least one of: a C19 species with a MW of 262 in an amount of 25-100 wt. %; a C19 species with a MW of 260 in an amount of 0-5 wt. %; a C19 species with a MW of 256 in an amount of 0-40 wt. %; a C19 species with a MW of 252 in an amount of 0-5 wt. %; a C13 species with a MW of 180 in an amount of 0-20 wt. %; and a C13 species with a MW of 174 in an amount of 0-5 wt. % (see claim 8). Nelson meets the limitations of the claims other than the differences that are set forth below.
Nelson does not specifically teach that the hydrogenated decarboxylated rosin acid composition has an oxygen content of <0.5 %. However, no unobviousness is seen in this difference because Nelson teaches that the unhydrogenated decarboxylated rosin acid composition has an oxygen content 0-2%, which would suggest that the hydrogenated DRC would meet the claim limitation of an oxygen content of <0.5 %.
Nelson does not specifically teach the oxidative stability was measured in terms of T onset of >168 C and T max of >183 C. However, no unobviousness is seen in this difference because Nelson performs an oxidation stability test which would be measured at the claimed onset and max temperatures.
Claims 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Nelson (US 20240093118) in view of Read (US 2,221,953-appears on the PTO-1449).
Nelson has been discussed above. Nelson teaches the hydrogenated decarboxylated rosin acid composition. However, Nelson does not teach the method of preparing the composition. Read teaches this difference.
Read teaches decarboxylating rosin acids as, for example, abietic acid, pimaric acid, and the like, followed by the hydrogenation of decarboxylated products to produce a fully saturated product having a boiling point above 300° C (see page 1, col. 2, lines 31-36).
The hydrogenation is conducted in a manner whereby hydrogen is added to a liquid decarboxylated product to substantially saturate the molecule. The hydrogenation is conducted in the presence of a suitable catalyst which is preferably a metal selected from group VIII of the periodic table. The pressure employed is in the range from 1500 to 6000 pounds per square inch and the temperature range from 140-250 C. The hydrogenation process may be one-stage or may be conducted in several stages (see page 1, lines 52-60; page 2, lines 1-12).
It would have been obvious to one of ordinary skill in the art to have prepared the hydrogenated decarboxylated rosin acid composition of Nelson by the method set forth in Read because Read teaches that hydrogenated decarboxylated rosin acid compositions prepared by his method are entirely stable, have high boiling points, will not distill out of oil when in service and will not adversely affect the flash characteristics of oil, which would be a properties desired by Nelson.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CEPHIA D TOOMER whose telephone number is (571)272-1126. The examiner can normally be reached Monday-Friday.
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/CEPHIA D TOOMER/Primary Examiner, Art Unit 1771 18887144/20260803
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