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 Objections
Claims 4 and 10 are objected to because of the following informalities:
compound is misspelled in the final line of Claim 4; and
in Claim 10, “and” after the last species listed on page 16 should be deleted, as several species are listed thereafter.
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 2 – 4, 8 – 10, 14, and 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 because:
There is a lack of antecedent basis for “the” compound obtainable by reacting the isophorone diisocyanate and the at least one isocyanate-reactive compound having at least one tertiary amino group set forth in Claim 2. It is then unclear which is of the “at least one” compound(s) obtainable by reacting the isophorone diisocyanate and the at least one isocyanate-reactive compound having at least one tertiary amino group are being referred to by the aforementioned phrase. The claims also do not previously set forth the at least one compound is obtainable by reacting in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents. For the purposes of further examination, Claim 2 will be interpreted as set forth said at least one compound is obtainable by reacting the isophorone diisocyanate and the at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents.
Claim 3 sets forth the composition of Claim 1 comprising “a” compound. As written, it is unclear if the compound recited in Claim 3 is an additional compound or refers to the at least one compound set forth in independent Claim 1. For the purposes of examination, the latter interpretation has been used.
Similarly, Claims 3 and 4 sets forth the composition of Claim 1 comprising “a” diluent. As written, it is unclear if the compound recited in Claim 3 is an additional diluent or refer to the diluent set forth in independent Claim 1. For the purposes of examination, the latter interpretation has been used.
There is a lack of antecedent basis for “the” compound set forth in Claim 4. Independent Claim 1 now sets forth at least one isocyanate-reactive compound having at least one tertiary amino group in two separate instances. It is then unclear which of the at least one compounds initially recited in Claim 1 is being referred to in the aforementioned dependent claim(s). For the purposes of further examination, “the” compound will be interpreted as referring to the at least one compound.
There is a lack of antecedent basis for “the” at least one isocyanate-reactive compound having at least one tertiary amino group set forth in Claims 8 and 10. Independent Claim 1 now sets forth at least one isocyanate-reactive compound having at least one tertiary amino group in two separate instances. It is then unclear which is being referred to in the aforementioned dependent claims. For the purposes of further examination, “the” at least one isocyanate-reactive compound having at least one tertiary amino group set forth in the dependent claims will be interpreted as referring to either the at least one isocyanate-reactive compound having at least one tertiary amino group which is reacted with isophorone diisocyanate or the at least one isocyanate-reactive compound having at least one tertiary amino group of the diluent.
There is a lack of antecedent basis for “the” isocyanate-reactive compound set forth in Claim 9. It is unclear if this phrase refers to either of the at least one isocyanate-reactive compounds having at least one tertiary amino group set forth in Claim 1. For the purposes of further examination, “the” isocyanate-reactive compound will be interpreted as referring to either the at least one isocyanate-reactive compound having at least one tertiary amino group which is reacted with isophorone diisocyanate or the at least one isocyanate-reactive compound having at least one tertiary amino group of the diluent.
There is lack of antecedent basis for “the” at least one compound obtainable by reacting the at least one isocyanate compound and the at least one isocyanate-reactive compound having at least one tertiary amino group optionally in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents in Claim 14. There is further a lack of antecedent basis for “the” compound in Claim 14. For the purposes of further examination, each phrase will be interpreted as referring to the at least one compound which is obtainable by reacting isophorone diisocyanate and at least one isocyanate-reactive compound having at least one tertiary amino group.
There is lack of antecedent basis for “the” compound(s) and “the” diluent(s) in Claim 16. The metes and bounds of the claim are also unclear, as the claim sets forth two different ranges of amounts for the diluent(s). It is further noted that a diluent is now required by independent Claim 1 and therefore the amount thereof in the composition must be greater than zero. For the purposes of further examination, Claim 16 will be interpreted as setting forth 10 to 99.991 wt% at least one compound which is obtainable by reacting isophorone diisocyanate and at least one isocyanate-reactive compound having at least one tertiary amino group and greater than 0 to 89.991 wt% of said diluent.
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 – 4, 8 – 12, 14 – 16, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2020/011343 to Karapetyan et al. (hereinafter Karapetyan) in view of GB 908,649 to Perry et al. (hereinafter Perry).
Regarding Claims 1, 4, and 15. Karapetyan teaches a composition comprising a catalysts including a tertiary compound of Formula (I) [0029] – [0030]. The tertiary amine compound is formed by reacting an isocyanate with a bicyclic tertiary aminoalcohol ([0037] and [0061]), wherein the hydroxyl group of the bicyclic tertiary aminoalcohol corresponds to an isocyanate-reactive group. Karapetyan further teaches its tertiary amine compound is an amino carbamate [0012], i.e. it has at least one carbamate group.
In Example 2, 26.59 mmol of isophorone diisocyanate, having two diisocyanate groups, is provided as the isocyanate; and 26.62 mmol RZETA® and 26.85 mmol of 2-[2-(dimethylamino)ethoxy]ethanol are reacted therewith [0094]. Each of these compounds corresponds to an isocyanate-reactive compound having at least one tertiary amino group. Using the aforementioned values, a molar excess of isocyanate-reactive compound can be calculated to be provided. [0178] of the PG-PUB of the instant application discloses that, when a molar excess of isocyanate-reactive compound is provided, this excess corresponds to a diluent of the composition. The molar excess of isocyanate-reactive compounds provided in Example 2 thus corresponds to a diluent comprising one isocyanate-reactive compound having at least one tertiary amino group.
Karapetyan teaches organometallic catalysts may also be provided in the composition [0070] – [0072] but not specifically a Cu(II) salt. However, Perry teaches the concept of providing Cu(II) salts, e.g. cupric acetate, as catalysts in polyurethane compositions (Page 1, Lines 9 – 13 and 51 – 73), most advantageously in conjunction with tertiary amines (Page 4, Lines 20 – 28). Karapetyan and Perry are analogous art as they are from the same field of endeavor, namely polyurethane foams. 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 a Cu(II) salt, e.g. cupric acetate, as the organometallic catalyst in Karapetyan. The motivation would have been that Perry teaches the use of such a catalyst leads to the preparation of foamed polyurethanes with superior mechanical properties, such as tear strength, resistance to compression, and resilience (Page 3, Lines 80 – 85).
Regarding Claim 2. Karapetyan teaches the composition of Claim 1. As Karapetyan teaches its tertiary amine compound is formed by reacting an isocyanate with a cyclic tertiary aminoalcohol [0037], it would be reasonably expected that this compound may be obtainable by reacting such compounds in the presence of at least one Cu(II) salt.
Regarding Claim 3. Karapetyan teaches the composition of Claim 1. Karapetyan does not expressly teach the at least one compound formed in Example 2 is further prepared with at least one isocyanate-reactive compound which does not have a tertiary amino group. However, in the disclosure, Karapetyan teaches its tertiary amine compound may be formed by reacting an isocyanate with a cyclic tertiary aminoalcohol and an additional alcohol/isocyanate-reactive compound which is not required to have a tertiary amino group [0061]. 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 use an additional alcohol/isocyanate-reactive compound in conjunction with the cyclic tertiary aminoalcohol in Example 1 of Karapetyan. The motivation would have been that it is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose. In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980) (MPEP 2144.06) In light of In re Kerkhoven, combining an additional alcohol/isocyanate-reactive compound and cyclic tertiary aminoalcohol would have been obvious given their known and shared intended use as isocyanate-reactive precursor for the preparation of the tertiary amine compound catalyst in Karapetyan.
This proposed modification of Karapetyan results in a compound formed by reacting the same compounds as in the instant claims. It would then be reasonably expected that this compound may be obtained by reacting the aforementioned precursors in the presence of at least one Cu(II) salt.
Regarding Claims 8 and 9. Karapetyan teaches the composition of Claim 1 wherein the isocyanate-reactive compounds having at least one tertiary amino group provided in Example 2 correspond to both the compound reacted with isophorone diisocyanate and the diluent. These compounds are RZETA® and 2-[2-(dimethylamino)ethoxy]ethanol [0094], which are each isocyanate-reactive compounds which are alcohols having at least one tertiary amino group. 2-[2-(dimethylamino)ethoxy]ethanol is, more specifically, an aliphatic alcohol having one hydroxyl group, one tertiary amino group, and one ether group.
Regarding Claim 10. Karapetyan teaches the composition of Claim 1 wherein the at least one isocyanate-reactive compound having at least one tertiary amino group which is reacted with isophorone diisocyanate and the at least one isocyanate-reactive compound having at least one tertiary amino group of the diluent corresponds to RZETA® [0094], which corresponds to the last structure depicted on page 12 of the claim set filed November 14, 2025.
Regarding Claims 11 and 12. Karapetyan teaches the composition of Claim 1 wherein isophorone diisocyanate, RZETA® and 2-[2-(dimethylamino)ethoxy]ethanol are provided in Example 2 [0094]. The compound may therefore reasonably considered to be the reaction product of isophorone diisocyanate and 2-[2-(dimethylamino)ethoxy]ethanol [0094] and correspond to one or more of the last four structures depicted in instant Claim 12.
Regarding Claim 14. Karapetyan teaches the composition of Claim 1. As Karapetyan teaches its tertiary amine carbamate is further combined with an isocyanate [0069] – [0070], it would be reasonably expected that the carbamate function will react with isocyanate to form an allophanate function as shown in [0167] of the PG-PUB of the instant application.
Regarding Claim 16. Karapetyan teaches the composition of Claim 1. In Example 2, 26.59 mmol of isophorone diisocyanate, having two diisocyanate groups, is provided as the isocyanate; and 26.62 mmol RZETA® and 26.85 mmol of 2-[2-(dimethylamino)ethoxy]ethanol are reacted therewith [0094]. Each of these compounds corresponds to an isocyanate-reactive compound having at least one tertiary amino group. Using the aforementioned values, a slight molar excess of isocyanate-reactive compound can be calculated to be provided. [0178] of the PG-PUB of the instant application discloses that, when a molar excess of isocyanate-reactive compound is provided, this excess corresponds to a diluent of the composition. The slight molar excess of isocyanate-reactive compounds provided in Example 2 thus corresponds to a diluent comprising one isocyanate-reactive compound having at least one tertiary amino group in an amount of slightly greater than 0 weight percent, with the remainder (less than 100 weight percent) corresponding to the compound obtained by reacting isophorone diioscyanate with the isocyanate-reactive tertiary amine compounds.
Regarding Claim 18. Karapetyan teaches the composition of Claim 1 may further comprise additional catalysts for producing polyurethane foams [0072].
Claims 19 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2020/011343 to Karapetyan et al. (hereinafter Karapetyan) in view of GB 908,649 to Perry et al. (hereinafter Perry), as applied to Claim 1 above, and further in view of US 6,423,756 to Ghobary et al. (hereinafter Ghobary).
Regarding Claims 19 and 20. Karapetyan teaches the composition of Claim 1 but does not expressly teach it further comprise a carboxylic acid. However, Ghobary teaches the concept of combining a tertiary amine catalyst with a carboxylic acid such as salicylic acid (Column 7, Lines 8 – 25). Karapetyan and Perry are analogous art as they are from the same field of endeavor, namely tertiary amine catalysts for polyurethane foams. 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 combine a carboxylic acid, such as salicylic acid, with the tertiary amine catalyst of Karapetyan. The motivation would have been that doing so may convert the tertiary amine catalyst to a delayed action catalyst, which Ghobary describes as catalysts which avoid the curing problems often associated with conventional catalysts (Column 2, Lines 52 – Column 3, Line 5; and Column 5, Lines 28 – 32).
Response to Arguments
Applicant's arguments filed November 14, 2025 have been carefully considered. The Office responds as follows:
A) The Office agrees that all outstanding objections to the claims and rejections under 35 U.S.C. 112(b), except where expressly noted above. The amendments to the claims also have resulted in a new claim objection and several new rejections under 35 U.S.C. 112(b) which are also set forth above.
B) With respect to the rejection under 35 U.S.C. 103 in view of Karapetyan and Perry, applicant argues that the fact that Perry employs copper (II) compounds as catalysts does not give a teaching or suggestion to employ such compounds with those of Karapetyan. However, specific motivation for providing copper(II) compounds in polyurethane foams, e.g. the polyurethane foams of Karapetyan, is expressly taught by Perry and cited in the outstanding and present Office actions. Namely, Perry
teaches the use of such catalysts leads to the preparation of foamed polyurethanes with
superior mechanical properties, such as tear strength, resistance to compression, and
resilience (Page 3, Lines 80 – 85).
C) Applicant additionally argues there is no teaching or suggestion in Karapetyan or Perry to employ an excess of isocyanate-reactive compound having at least one tertiary amino group as a diluent. The Office respectfully disagrees.
In Example 2 of Karapetyan, 26.59 mmol of isophorone diisocyanate, having two diisocyanate groups, is provided as the isocyanate; and 26.62 mmol RZETA® and 26.85 mmol of 2-[2-(dimethylamino)ethoxy]ethanol are reacted therewith [0094]. Each of these compounds corresponds to an isocyanate-reactive compound having at least one tertiary amino group. Using the aforementioned values, a molar excess of isocyanate-reactive compound can be calculated to be provided. [0178] of the PG-PUB of the instant application discloses that, when a molar excess of isocyanate-reactive compound is provided, this excess corresponds to a diluent of the composition. The molar excess of isocyanate-reactive compounds provided in Example 2 of Karapetyan thus corresponds to a diluent comprising one isocyanate-reactive compound having at least one tertiary amino group.
D) Applicant’s arguments with respect to the rejection under 35 U.S.C. 103 in view of primary reference Ghobary are hereby moot, as this rejection has been withdrawn in light of the amendments to the instant claims. Ghobary is now only relied upon only as a secondary reference for its teachings with respect to the combination of carboxylic acids with tertiary amine catalyst compositions.
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
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/MELISSA A RIOJA/Primary Examiner, Art Unit 1764