DETAILED ACTION
Status of Application
This action follows a reply filed on 03/27/2026. Per the reply, claims 1 and 20 have been amended and claim 6 has been cancelled. No new claims have been added. Accordingly, claims 1-5 and 7-20 remain pending and under examination herein.
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 .
Withdrawn Objection(s)/Rejection(s)
Any objection or rejection set forth in the previous Office action, but not explicitly repeated herein, is hereby withdrawn.
Common Ownership Notice
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 Rejections – 35 U.S.C. 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 1-5, 7-12, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Crowther (US 3853960), alone, or as evidenced by Pentaerythritol Product Specification (hereinafter, ‘Product Specification’).
Regarding Claims 1-4, 8 and 16-18, reference to Crowther relates to pentaerythritol tetracarbamate and a method for its manufacture by transesterification of pentaerythritol with a lower alkyl carbamate (col.1, lines 8-11) as well as to use of the product as an intermediate in the formation of methylol derivatives (corresponding to claimed “carbamate-functional material”) for the treatment of cellulosic fabrics, production of coatings or resins (col. 5, lines 13-16). Specific disclosure is provided in Examples 1, 3 and 4 to preparing pentaerythritol tetracarbamate by reacting prescribed amounts of pentaerythritol (corresponding to claimed "compound having at least one hydroxy group is … polyols having 2 to 160 carbon atoms …") with ethyl carbamate (Ex. 1), butyl carbamate (Ex. 3) and beta-methoxyethyl carbamate (Ex. 4), the reaction in each case being performed in the presence of the same catalyst, viz., dibutyl tin oxide (corresponding to claimed "tin containing catalyst" (of claim 1) and "dialkyl tin oxides" (of claim 8)). Crowther further states that in other cases, "propyl, isobutyl and methyl carbamates in amounts of about 8 mols per mol of pentaerythritol were used instead of ethyl carbamate with good results" (col. 2, line 66 to col. 3, line 2).
Crowther does not directly disclose reacting the compound having at least one hydroxy group with an alkyl carbamate of general formula (I) in which R1 is an organic residue bearing at least one tertiary carbon atom, such as aliphatic tertiary C4 to C12 alkyl residues [for claim 2] or tert-butyl [for claim 4] or aliphatic tertiary C4 to C10 alkyl residues [for claim 16] or aliphatic tertiary C4 to C6 alkyl residues [for claim 17] or aliphatic tertiary C4 residues [for claim 18].
Nevertheless, as noted, Crowther describes use of butyl carbamate and isobutyl carbamate as the lower alkyl carbamate reactant with pentaerythritol. Given their close structural relationship as position isomers sharing a common utility as reactant in preparing carbamate-functional material, an artisan of ordinary skill would have reasonably expected tert-butyl carbamate to possess similar properties to the disclosed isobutyl- and butyl carbamate compounds, including similar reactivity with pentaerythritol in the transesterification of Crowther. The expectation of equivalent performance would have provided the requisite motivation for one of ordinary skill in the art to modify the method of Crowther by substituting isobutyl- or butyl-carbamate by the corresponding tert-butyl ester. Indeed, structural relationships, particularly when coupled with a common utility, may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds, see MPEP § 2144.08II(c). Thus, the subject matter of claims 1-4, 8 and 16-18 would have been prima facie obvious to a person having ordinary skill in the art at the time of the invention.
Regarding Claims 5 and 19-20, Crowther renders obvious the method according to claim 1 as discussed above. Further, while Crowther does not directly disclose average OH-functionality of the
pentaerythritol reagent, it is well-known in the art that pentaerythritol has a hydroxy value of 1625-
1650 mgKOH/g and a molecular weight (MW) of 136.15 g/mol as evidenced by Product Specification.
Based on such properties, one may calculate the average OH-functionality of this reagent as follows:
equivalent weight, EW = 56100/hydroxy value; average functionality, f = MW/EW. Hence, for the
minimum hydroxy value of 1625 mgKOH/g, EW = 34.5 (56100/1625) and f = 3.95 (136.15/34.5); and for
the maximum hydroxy value of 1650 mgKOH/g, EW = 34 (56100/1650) and f = 4.00 (136.15/34). Thus,
Crowther's pentaerythritol reagent is considered to intrinsically possess an average OH-functionality
within the claimed range for each of said claims.
Regarding Claim 7, Crowther renders obvious the method according to claim 1 as discussed above. Crowther further teaches to employ the carbamate ester in a proportion relative to the pentaerythritol in the molecular excess of that required to form the tetracarbamate, i.e., "at least 4 mols of the carbamate ester per mol of pentaerythritol" (col. 4, lines 7-11). In light of this teaching, it is considered that the claimed subject matter as a whole would have been obvious to one having ordinary skill in the art prior to the effective filing date of the claimed invention, since it has been held that choosing the overlapping portion, of the range taught in the prior art ("at least 4 mols .") and the range claimed by the applicant (molar ratio of 1.5 to 5"), has been held to establish a prima facie case of obviousness, see In re Woodruff, 16 USPQ2d 1936 (claimed invention rendered obvious by prior art reference whose disclosed range ("about 1-5% carbon monoxide") abutted the claimed range ("more than 5% to about 25%" carbon monoxide), In re Geisler, 43 USPQ2d at 1365 (acknowledging that claimed invention rendered prima facie obvious by prior art reference whose disclosed range (50-100 Angstroms) overlapped the claimed range (100-600 Angstroms)) and MPEP § 2144.05.
Regarding Claim 9, Crowther renders obvious the method according to claim 1 as discussed above. Crowther further expresses preference for adding a catalyst to the reaction mixture to promote the transesterification and teaches the advantageous use of between 0.1 and 1 percent and especially 0.2 to 0.5 %, based upon the combined of pentaerythritol and carbamate ester (col. 4, lines 15-20). The disclosed ranges for amount of added catalyst are fully embraced by the claimed range of 0.01 to 1 wt.%, and dibutyl tin oxide is the only catalyst used in all preparation examples of Crowther. Thus, it would have been obvious to one having ordinary skill in the art prior to the date of effective filing to undertake the method of Crowther using a tin-containing catalyst in an amount within the claimed range for this parameter.
Regarding Claim 10, Crowther renders obvious the method according to claim 1 as discussed above. Crowther further discloses that temperatures between 135° and 170°C are advantageously employed in carrying out the transesterification reaction (col. 4, lines 52-59). The disclosed range substantially overlaps the claimed range for reaction temperature, and it has consistently been held that even a slight overlap in ranges establishes a prima facie case of obviousness, as discussed above with respect to claim 7. See MPEP § 2144.05.
Regarding Claim 11, Crowther renders obvious the method according to claim 1 as discussed above. Further, Crowther's description of the product of the disclosed preparation as "the tetracarbamate of pentaerythritol" (col. 1, lines 58-59) indicates that four of the five hydroxy groups of pentaerthyritol are replaced by carbamate groups in the product, affording an 80% replacement rate, which falls well within the claimed range of "at least 75% of the hydroxy groups are replaced with carbamate groups."
Regarding Claim 12, Crowther renders obvious the method according to claim 1 as discussed above; further, the aforementioned methylol derivatives of pentaerythritol tetracarbamate as obtained from the intermediate formed by reacting tert-butyl carbamate with pentaerythritol as per the modified method of Crowther are seen to qualify as “carbamate-functional material” as claimed.
Claims 12-15 are rejected under 35 U.S.C. 103 as being unpatentable over Jadhav (US 2015/0321998 A1).
Regarding Claim 12, the claim is drawn to a carbamate-functional material prepared by the
method according to claim 1. Reference to Jadhav is directed to carbamate-functional material
prepared by reacting a carbamate compound with a hydroxy-functional compound using zirconium
acetylacetonate as catalyst, wherein the hydroxy-functional compound may have one or a plurality of
hydroxyl groups (¶ [0005]). Transcarbamation of C36 Dimer diol and of acrylic polymers using methyl
carbamate is specifically described (¶¶ [0069]-[0071] (Examples 1-3)). While methyl carbamate differs
from claimed formula (I) due to lack of an organic residue bearing at least one tertiary carbon atom,
Jadhav mentions as examples of suitable carbamate compounds: methyl carbamate, ethyl carbamate, n-propyl carbamate, isopropyl carbamate, n-butyl carbamate, isobutyl carbamate, tert-butyl carbamate, n-
hexyl carbamate, 2-ethylhexyl carbamate, cyclohexyl carbamate, phenyl carbamate, hydroxypropyl
carbamate, hydroxyethyl carbamate, and combinations of these (¶ [0010]; see also claim 3). Among
the listed compounds, at least tert-butyl and 2-ethylhexyl carbamates are compounds with
an organic residue bearing a tertiary carbon atom in compliance with claimed formula (I), and which are
considered as viable equivalents to methyl carbamate for the purposes of Jadhav. It would have been
obvious to one of ordinary skill in the art to substitute methyl carbamate by tert-butyl or
2-ethylhexyl carbamate in the disclosed transcarbamation procedure, as these carbamates are all
considered to be equivalents known for the same purpose. Simple substitution of one known material
for another to obtain predictable results, provides the rationale for a prima facie case of obviousness.
See MPEP § 2143. Further, although the carbamate-functional material of Jadhav is prepared in
presence of a catalyst different to that used in the instant method (i.e., Zr acetylacetonate vs. tin-
containing catalyst), there is no record evidence of any patentably distinguishing feature(s) between the
carbamate-functional material as obtained using the Jadhav catalyst and that obtained by the method
according to claim 1 herein. In this regard, note that a difference in preparation, to be of patentable
significance, must result in a substantially different product than that obtained by the prior art process.
See MPEP § 2113.
Regarding Claims 13-14, Jadhav renders obvious at least one carbamate-functional material
according to claim 12 as discussed above. Jadhav further teaches the utility of such material in coating
compositions, including a clearcoat or tinted clearcoat composition as claimed (¶¶ [0048], [0054]-
[0056]).
Regarding Claim 15, Jadhav renders obvious the coating composition according to claim 13 as
discussed above. Jadhav further teaches a method of coating a substrate, comprising applying said coating composition at least partly to the substrate and curing said applied coating composition (¶¶ [0058], [0062]-[0064]).
Response to Argument
Applicant's arguments filed 03/27/2026 have been fully considered but they are not persuasive.
With respect to Crowther, Applicant’s argument is essentially two-fold: (i) that Crowther does not disclose or suggest further reacting its final carbamate compound with an additional compound having at least one hydroxy group in the presence of a tin-containing catalyst to form a different carbamate-functional material; and (ii) that Crowther’s carbamates, including isobutyl carbamate, do not necessarily include a tertiary carbon atom (Reply at 6).
As to point (i), it is firstly noted that Crowther does in fact disclose further reacting its final carbamate compound with an additional compound having at least one hydroxy group, in particular as an intermediate in the formation of methylol derivatives of pentaerythritol tetracarbamate, which Crowther describes as “new products of commercial importance, particularly for use in finishing fabrics comprising cellulosic fibers” (col. 5, lines 14-21). Furthermore, present claim 1 only requires a tin-containing catalyst be present in the recited reaction of at least one alkyl carbamate compound of general formula (I) and at least one compound having at least one hydroxy group. There is no positive limitation that the same catalyst must be present or used in forming a different carbamate-functional material in some unspecified subsequent reaction. In fact, claim 1 is silent as to reaction conditions whereby the reaction product of the recited reaction is further reacted to form a different carbamate-functional material.
As to point (ii): even if Crowther’s named carbamates do not necessarily include a tertiary carbon atom, the fact remains that both the butyl carbamate and the isobutyl carbamate (used in Crowther’s Example 3) are closely related as position isomers to tert-butyl carbamate and they all share a common utility as reactants in preparing carbamate-functional material. The expectation of equivalent performance based on this close structural relationship would have provided the requisite motivation for one of ordinary skill in the art to modify the method of Crowther by substituting isobutyl- or butyl-carbamate by the corresponding tert-butyl ester.
Further at to point (ii), it is noted that the comparative data of record involves only a comparison of embodiments of the claimed invention wherein the alkyl carbamate compound is tert-butyl carbamate, with three comparative embodiments, all of which employ methyl carbamate (see Spec., Comparative Examples 1-3 on pp. 30-31). However, it is well settled that evidence of unexpected results must relate to the closest prior art, In re DeBlauwe, 222 USPQ 191, 196 (Fed. Cir. 1984). Thus, the critical comparison should involve use of the butyl and isobutyl carbamates of Crowther under otherwise identical reaction conditions. There being no comparative data comparing the method of the present invention with the closest embodiments of Crowther, Applicant's assertion of unexpected results/improvements in the use of a combination of tert-butyl carbamate and a tin-based catalyst (Reply at 8) is not probative of patentability.
With respect to Jadhav, Applicant argues only that Jadhav is directed to the use of zirconium acetylacetonate as a catalyst and expressly seeks to avoid tin-based catalysts, citing paragraphs [0006] and [0045] (Reply at 7).
This argument lacks persuasiveness because, as pointed out above and in the previous Office action, present claim 12 is drawn to a carbamate-functional material claimed as a product, in product-by-process format, which requires a lesser burden of proof on the part of the examiner with regard to the process aspects of preparing the product. Where, as here, the examiner meets this lesser burden of proof, it is in fact applicants’ burden to show that the polymer product is actually different. “The Patent Office bears a lesser burden of proof in making out a case of prima facie obviousness for product-by-process claims because of their peculiar nature” than when a product is claimed in conventional fashion. In re Fessmann, 180 USPQ 324, 326 (CCPA 1974). Similarly, claims 13-14 are drawn to coating compositions comprising the carbamate-functional material according to claim 12, and claim 15 is drawn to a method of coating a substrate using the coating composition according to claim 13. To the extent that Jadhav seeks to avoid tin-based catalysts, the test data of record do not purport to demonstrate criticality in the use of a tin-based catalyst versus the zirconium acetylacetonate catalyst of Jadhav. That is, the specification examples fail to show that carbamate-functional material prepared according to the claimed method differs materially from the carbamate-functional material obtained using the Jadhav catalyst. Examiner therefore finds that the evidence of record is insufficient to rebut the prima facie case based on Jadhav.
Conclusion
Claims 1-5 and 7-20 stand rejected. No claims are in condition for allowance at this time.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/06-04-26
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