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 .
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1 – 4, 6 – 8, and 11 – 20 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The species of 2,2-bis(hydroxymethyl)phenylacetic acid and 2,2-bis(hydroxymethyl)tolylacetic acid now set forth in independent Claims 1 and 11 are not supported by the original disclosure. The instant specification does not expressly set forth either specie and the genus of possible compounds encompassed by Formula I is large enough that neither specie would be at once envisaged by the disclosure. As all remaining pending claims ultimately depend on Claim 1 or Claim 11, they incorporate the subject matter thereof and are also therefore rejected under this statute.
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.
Claims 1 – 3, 7, and 8 are rejected under 35 U.S.C. 103 as being unpatentable over CA 2 742 538 to Nefzger et al.
Regarding Claims 1 and 7. Nefzger teaches a polyurethane foam composition comprising:
an isocyanate compound;
a polyester polyol, i.e. an isocyanate-reactive compound;
a blowing agent; and
optionally auxiliary substances and additives (see last two paragraphs of Page 6 and lines 1 – 3 of Page 7).
The polyester polyol is the esterification product of at least one carboxylic anhydride and diethylene glycol (see last paragraph of Page 2). The at least one carboxylic anhydride is preferably aromatic (see second full paragraph of Page 3); in such embodiments, the polyester polyol corresponds to an aromatic polyester polyol based on an aromatic acid component. Diethylene glycol corresponds to an aliphatic diol compound.
The reaction mixture which forms the polyester polyol may also further comprise dimethylolpropionic acid (see fifth full paragraph of Page 5). The Office recognizes that dimethylolpropionic acid, which is alternatively known in the art as 2,2,-bis(hydroxymethyl)propionic acid, does not correspond to one of the instantly claimed species of dialkylol alkanoic acid compounds. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties. In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See also In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990)
In the instant case, one of ordinary skill in the art would have been motivated to make 2,2-bis(hydroxymethyl)butanoic acid in the expectation that this compound has a similar structure and properties to Nefzger’s 2,2,-bis(hydroxymethyl)propionic acid. 2,2-dimethylolpropionic acid corresponds to a homolog of instantly claimed 2,2-bis(hydroxymethyl)butanoic acid, as the compounds differ only by the successive addition of -CH2- in the alkyl chain attached to the central carbon atom of the compound. 2,2-bis(hydroxymethyl)butanoic acid in the instant application and 2,2-bis(hydroxymethyl)propionic acid in Nefzger also have the same utility as higher functional alcohol starters which react with aromatic acid compounds to form polyester polyols. It has been held that compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
Nefzger does not expressly teach that the aromatic polyester polyol is liquid at 25°C and is silent regarding its viscosity in comparison to a corresponding polyol compound made to the same hydroxyl number, aromatic content, and calculated functionality but without the use of component (iii). Consequently, the Office recognizes that all of the claimed effects or physical properties are not positively stated by the reference(s). However, Nefzger, when modified in the manner proposed, teaches a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process. Therefore, the claimed effects and physical properties - i.e. an aromatic polyester polyol that is liquid at 25°C and has a viscosity in comparison to a corresponding polyol compound made to the same hydroxyl number, aromatic content, and calculated functionality but without the use of component (iii) - would implicitly be achieved in a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process. See In Re Spada, 911, F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990) and MPEP 2111.01 (I)(II). If it is applicant’s position that this would not be the case: (1) evidence would need to be provided to support the applicant’s position and (2) it would be the Office’s position that the application contains inadequate disclosure as to how to obtain the claimed properties in a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process.
Regarding Claim 2. Nefzger teaches the polyurethane foam composition of Claim 1 wherein the viscosity of the aromatic polyester polyol ranges from preferably 400 to 3000 mPa∙S (see first full paragraph of Claim 5), i.e. 400 to 3000 centipoise.
Regarding Claim 3. Nefzger teaches the polyurethane foam composition of Claim 1 wherein the acid value of the aromatic polyester polyol ranges from 0.5 to 3.5 mgKOH/g (see fourth full paragraph of Claim 5)
Regarding Claim 8. Nefzger teaches the polyurethane foam composition of Claim 1 wherein the aromatic polyester polyol has an average functionality of 1.9 to 3 (see fourth full paragraph of Page 5). The aromatic polyester polyol is further indicated to have a hydroxyl value in the range of 150 to 320 mgKOH/g (see last full paragraph of Page 4); an acid value of from 0.5 to 3.5 mgKOH/g (see fourth full paragraph of Claim 5); and a viscosity of from preferably 400 to 3000 mPa∙S (see first full paragraph of Claim 5), i.e. 400 to 3000 centipoise.
Claims 4 and 6 are rejected under 35 U.S.C. 103 as being unpatentable over CA 2 742 538 to Nefzger et al., as applied to Claim 1 above, and further in view of US 2016/0053057 to Tabor et al. (hereinafter Tabor).
Regarding Claim 4. Nefzger teaches the polyurethane foam composition of Claim 1 wherein the aromatic polyester polyol compound is made from at least one carboxylic acid anhydride (A) and diethylene glycol (B), in a combined weight of 66 – 95 weight percent. The remainder of the composition, i.e. 5 to 34 weight percent, may comprises component (F) (see paragraph spanning Pages 2 – 3). Component (F) is particularly preferably succinic acid (see second full paragraph of Page 4).
Nefzger does not expressly teach the succinic acid is bio-based. However, Tabor teaches the concept of using bio-based succinic acid in the preparation of polyester polyols [0267]. Nefzger and Tabor are analogous art as they are from the same field of endeavor, namely polyester polyols. Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to provide bio-based succinic acid as the succinic acid component in Nefzger. 5 to 34 weight percent of aromatic polyester polyol would then comprise a bio-based material. The motivation would have been that Tabor teaches the use of bio-renewable materials is desirable in the art as a sustainable replacement for petroleum-based materials [0005].
Regarding Claim 6. Nefzger teaches the polyurethane foam composition of Claim 1 wherein the aromatic polyester polyol compound is made from at least one carboxylic acid anhydride (A) and diethylene glycol (B), in a combined weight of 66 – 95 weight percent (see paragraph spanning Pages 2 – 3).
Nefzger does not expressly teach the diethylene glycol is recycled. However, Tabor teaches the concept of using recycled diethylene glycol in the preparation of polyester polyols [0196]. Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to provide recycled diethylene glycol as the diethylene glycol component in Nefzger. 66 to 95 weight percent of aromatic polyester polyol would then comprise a recycled material. The motivation would have been that Tabor teaches diethylene glycol may be recovered from deicing fluids [0196], thus providing a new use for a waste product and reducing costs associated with production of the aromatic polyester polyol.
Claims 11 – 13 and 16 – 20 are rejected under 35 U.S.C. 103 as being unpatentable over CA 2 742 538 to Nefzger et al.
Regarding Claims 11 and 16. Nefzger teaches a method of forming a polyurethane product comprising reacting, in the presence of a blowing agent, an isocyanate compound; and a polyester polyol, i.e. an isocyanate-reactive compound (see last two paragraphs of Page 6).
The polyester polyol is the esterification product of at least one carboxylic anhydride and diethylene glycol (see last paragraph of Page 2). The at least one carboxylic anhydride is preferably aromatic (see second full paragraph of Page 3); in such embodiments, the polyester polyol corresponds to an aromatic polyester polyol prepared from an aromatic acid compound. Diethylene glycol corresponds to an aliphatic diol compound.
The reaction mixture which forms the polyester polyol may also further comprise dimethylolpropionic acid (see fifth full paragraph of Page 5). The Office recognizes that dimethylolpropionic acid, which is alternatively known in the art as 2,2,-bis(hydroxymethyl)propionic acid, does not correspond to one of the instantly claimed species of dialkylol alkanoic acid compounds. However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties. In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See also In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990)
In the instant case, one of ordinary skill in the art would have been motivated to make 2,2-bis(hydroxymethyl)butanoic acid in the expectation that this compound has a similar structure and properties to Nefzger’s 2,2,-bis(hydroxymethyl)propionic acid. 2,2-dimethylolpropionic acid corresponds to a homolog of instantly claimed 2,2-bis(hydroxymethyl)butanoic acid, as the compounds differ only by the successive addition of -CH2- in the alkyl chain attached to the central carbon atom of the compound. 2,2-bis(hydroxymethyl)butanoic acid in the instant application and 2,2-bis(hydroxymethyl)propionic acid in Nefzger also have the same utility as higher functional alcohol starters which react with aromatic acid compounds to form polyester polyols. It has been held that compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
Nefzger does not expressly teach that the aromatic polyester polyol is liquid at 25°C and is silent regarding its viscosity in comparison to a corresponding polyol compound made to the same hydroxyl number, aromatic content, and calculated functionality but without the use of component (iii). Consequently, the Office recognizes that all of the claimed effects or physical properties are not positively stated by the reference(s). However, Nefzger, when modified in the manner proposed above, teaches a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process. Therefore, the claimed effects and physical properties - i.e. an aromatic polyester polyol that is liquid at 25°C and has a viscosity in comparison to a corresponding polyol compound made to the same hydroxyl number, aromatic content, and calculated functionality but without the use of component (iii) - would implicitly be achieved in a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process. See In Re Spada, 911, F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990) and MPEP 2111.01 (I)(II). If it is applicant’s position that this would not be the case: (1) evidence would need to be provided to support the applicant’s position and (2) it would be the Office’s position that the application contains inadequate disclosure as to how to obtain the claimed properties in a product prepared from all of the claimed ingredients in the claimed amounts by a substantially similar process.
Regarding Claim 12. Nefzger teaches the method of Claim 11 wherein the viscosity of the aromatic polyester polyol ranges from preferably 400 to 3000 mPa∙S (see first full paragraph of Claim 5), i.e. 400 to 3000 centipoise.
Regarding Claim 13. Nefzger teaches the method of Claim 11 wherein the acid value of the aromatic polyester polyol ranges from 0.5 to 3.5 mgKOH/g (see fourth full paragraph of Claim 5)
Regarding Claim 17. Nefzger teaches the method of Claim 11 wherein the aromatic polyester polyol has an average functionality of 1.9 to 3 (see fourth full paragraph of Page 5). The aromatic polyester polyol is further indicated to have a hydroxyl value in the range of 150 to 320 mgKOH/g (see last full paragraph of Page 4); an acid value of from 0.5 to 3.5 mgKOH/g (see fourth full paragraph of Claim 5); and a viscosity of from preferably 400 to 3000 mPa∙S (see first full paragraph of Claim 5), i.e. 400 to 3000 centipoise.
Regarding Claims 18 and 19. Nefzger teaches the method of Claim 12 wherein the aromatic polyester polyol is prepared under esterification reaction conditions including a temperature of 100 to 230°C. Esterification may occur in the presence of an esterification catalyst (see first full paragraph of Page 6).
Nefzger does not provide a general teaching with respect to reaction time period and quantity of esterification catalyst. However, the experimental modification of this prior art in order to ascertain optimum operating conditions fails to render applicants' claims patentable in the absence of unexpected results. In re Aller, 220 F.2d 454, 105, 105 USPQ 233 (CCPA 1955) (MPEP 2144.05) Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to optimize the reaction time period and quantity of esterification catalyst to ensure a complete and efficient reaction of the components of the reactive mixture. A prima facie case of obviousness may be rebutted, however, where the results of the optimizing variable, which is known to be result-effective, are unexpectedly good. In re Boesch and Slaney, 617 F.2d 272, 205, 205 USPQ 215 (CCPA 1980) (MPEP 2144.05)
Regarding Claim 20. Nefzger teaches the method of Claim 12 further comprises applying the reactive mixture as a metal composite of a profiled roof element (see last paragraph of Page 9).
Claims 14 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over CA 2 742 538 to Nefzger et al., as applied to Claim 1 above, and further in view of US 2016/0053057 to Tabor et al. (hereinafter Tabor).
Regarding Claim 14. Nefzger teaches the method of Claim 11 wherein the aromatic polyester polyol compound is made from at least one carboxylic acid anhydride (A) and diethylene glycol (B), in a combined weight of 66 – 95 weight percent. The remainder of the composition, i.e. 5 to 34 weight percent, may comprises component (F) (see paragraph spanning Pages 2 – 3). Component (F) is particularly preferably succinic acid (see second full paragraph of Page 4).
Nefzger does not expressly teach the succinic acid is bio-based. However, Tabor teaches the concept of using bio-based succinic acid in the preparation of polyester polyols [0267]. Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to provide bio-based succinic acid as the succinic acid component in Nefzger. 5 to 34 weight percent of aromatic polyester polyol would then comprise a bio-based material. The motivation would have been that Tabor teaches the use of bio-renewable materials is desirable in the art as a sustainable replacement for petroleum-based materials [0005].
Regarding Claim 15. Nefzger teaches the method of Claim 11 wherein the aromatic polyester polyol compound is made from at least one carboxylic acid anhydride (A) and diethylene glycol (B), in a combined weight of 66 – 95 weight percent (see paragraph spanning Pages 2 – 3).
Nefzger does not expressly teach the diethylene glycol is recycled. However, Tabor teaches the concept of using recycled diethylene glycol in the preparation of polyester polyols [0196]. Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to provide recycled diethylene glycol as the diethylene glycol component in Nefzger. 66 to 95 weight percent of aromatic polyester polyol would then comprise a recycled material. The motivation would have been that Tabor teaches diethylene glycol may be recovered from deicing fluids [0196], thus providing a new use for a waste product and reducing costs associated with production of the aromatic polyester polyol.
Terminal Disclaimer
The terminal disclaimer filed on March 2, 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of any patent granted on U.S. Application No. 18/039,302 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Arguments
Applicant's arguments filed March 2, 2026 have been fully considered. The Office responds as follows:
Claim Objections
The Office agrees that the amendments to the claims are sufficient to overcome the outstanding claim objections. All claim objections have consequently been withdrawn.
Rejection of Claims 1 – 20 under 35 U.S.C. 112
The Office agrees that the amendments to the claims are sufficient to overcome the outstanding rejections under 35 U.S.C. 112(b) and (d). Each of these rejections has consequently been withdrawn.
Rejection of Claims 1 – 3, 5, 7 – 13, and 16 – 20 under 35 U.S.C. 102
Applicant argues that the amendments to independent Claims 1 – 11 set forth dialkylol alkanoic acid compounds which are not taught by the prior art. The Office agrees that Nefzger does not expressly teach any of the compounds presently set forth and therefore does not anticipate the instant claims as amended. The outstanding rejections under 35 U.S.C. 102 are therefore withdrawn. However, it is the Office’s position that Nefzger does render obvious the instant claims as amended, as detailed in the new grounds of rejection under 35 U.S.C. 103 set forth in the present action.
Rejection of Claims 4, 6, 14, and 15 under 35 U.S.C. 103
Applicant argues Tabor fails to cure the deficiencies of Nefzger. However, the Office maintains that Nefzger is suitably relied upon to render obvious the newly present subject matter in the claims for the reasons detailed in the new grounds of rejection under 35 U.S.C. 103.
Double Patenting
The Office agrees that the terminal disclaimer filed on March 2, 2026 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of any patent granted on U.S. Application No. 18/039,302 obviates the outstanding obviousness-type double patenting rejection. The outstanding obviousness-type double patenting rejection has therefore been withdrawn.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 MELISSA RIOJA whose telephone number is (571)270-3305. The examiner can normally be reached Monday - Friday 10:00 am - 6:30 pm EST.
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/MELISSA A RIOJA/Primary Examiner, Art Unit 1764