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 .
Response to Arguments
In their response dated 7/7/2026 the applicant amended claim 1 to require polycarbodiimide to be capped with a compound of formula 1 having molecular weight of 208 or less.
The office action dated 4/7/2026 when addressing the capping agent for the polycarbodiimide indicated that the capping agent having the same formula as that of applicants has the integer m defining the amount of ethylene oxide units in a range of 2-6 [0075] consequently limiting molecular weight of the capping agent to 208 would not overcome the teachings of Tsukamoto. This is because when number of ethylene oxide repeat units is 4, the molecular weight of the capping agent is exactly 208.
Amendment further results in the 112 issues, because the capping agent of formula 1 is specifically limited to R1 being methyl and integer m being 4. The molecular wight of this compound is exactly 208, consequently term “or less” raises 112 2nd paragraph issue. The term “or less” is not rejected for written description requirement only because it was a language originally included in claim 1, when the molecular weight of the capping agent was 300 or less.
With respect to applicants’ arguments directed to experimental section and specifically Tables A and B:
Table A discloses composition where the polycarbodiimide A has degree of polymerization of 5 exactly, capping agent has molecular weight of exactly 550. Polycarbodiimide B has degree of polymerization of exactly 5 and capping agent has molecular weight of 208 and 252. Ratio of A to B is 60:40.
Table B discloses properties of waterborne polyurethane composition, waterborne polyester composition and waterborne acrylic composition.
Content of A and B is within the claimed range, but not entire range. The properties argued are those of the resin composition and not the crosslinking agent itself. This means that the coating is also cured where the chemical structure of the crosslinking agent will change. Claim 11 is open to any waterborne resin not just those disclosed in Table B.
The examiner further evaluated table 1 which discloses many more examples which disclose following:
Polycarbodiimide A: utilized isocyanate HMDI, degree of polymerization 3, 5, 10 and 15 with preferred degree of 5, capping agents having molecular weight of 550 being preferred, however mw of 385, 400, 900 and 1000 are also disclosed. Content of A 5, 20, 30, 40, 50, 60, 70, 80 and 90 with 40 and 60 being preferred.
Polycarbodiimide B: utilized isocyanate HMDI, TMXHI, IDPI, TDI, XDI, with HMDI being preferred. The degree of polymerization 3, 5, 10, 15, 20 with preferred degree of 5. Content of B is 10, 20, 30, 40, 50, 60, 70, 80 and 95 with 40 and 60 being preferred.
Consequently, Table 1 is viewed as more detailed presenting more examples with respect to the content of A and B. Comparing Table 1 with properties of Table 2 following are examiner’s observations:
Instant claim 1 requires content of compound A to be in a range of 15-60 parts per total content of polycarbodiimides, which would men that compound B would be in a range of 40-85.
Degree of polymerization for both A and B are 3-10. Capping agent A is mostly 550 and capping agent for B is mostly 208,
Examples 1, 2 and 3 component A has degree of polymerization3 , 5 and 10 and content of 40. Component B has degree of polymerization of 5 and content of 60. The properties are given rating A.
Examples 5 and 6 disclose A with polymerization degree of 5, content 40 and B with polymerization degree of 3 and 10 with content of 60. Examples 5 have rating A.
Examples 10-39 have A with degree of polymerization of 5 content varies, A has degree of polymerization 5 and content varies such that both compounds add up to 100. The results are mixed.
Component B has isocyanate component which is HMDI, IPDI and XDI. Component A is only HMDI.
For A being HMDI degree of polymerization at 5 varying content and for B having one of the isocyanates listed above, degree of polymerization at 5 varying contents:
Examples 17, 28-31 with A to B content 40:60 or 40:60 as encompassed by instant claims, the highest rating is B.
The aspect of the experimental data that is unclear is the method in which ratings A-E were determined:
Pot life was determined by change of viscosity and it was measured using viscometer. The rating was reflective of the percentage of change in viscosity.
Glossiness of the cured film measured at 60o with handy gloss meter. It is not clear what the applicants mean when criteria is, for example, glossiness increase by 8 or more with respect to black. What does it mean “by 8”? Why 8?
Solvent resistance was measured by rubbing test piece with absorbent cotton impregnated with 70% by mas ethanol solution. Rubber back and forth 50 times. The solvent resistance is reflective of the whitening properties and remaining area of the coating film. The specification is silent in how exactly the two values were measured, specifically, was the percentage determined using some sort of test equipment or simple eyeball? In the even eyeball is used, the test results are not reliable because they are subjective to human error and approximation. Examiner’s 75% will not necessarily be the 75% determined by the applicants. The final score is an average of two properties with undefined measurement methods.
Interlayer adhesion test is outside of the scope of the instant invention as it is dependent on the properties of two layers, primer layer and overcoat layer in a multilayered article.
In summary, with respect to the crosslinker, instant specification does not disclose any test data which would pertain only to crosslinker.
The only property that is attributed to resin composition is a pot life, however, instant claims encompass many more polymers than what examples entail.
Waterborne film properties are properties of cured layer, here again instant claims encompass any waterborne polymer composition capable of forming a film and utilizing carbodiimide as crosslinker.
With the mixed test results for examples within applicant’s claimed ranges, the provided data is not viewed as unexpected because claimed composition shows good results and not so good.
As this point all the prior art rejections are maintained.
New 112 2nd paragraph rejection is issued.
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 1, 6-17 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.
Instant claim 1 recites compound of formula 1:
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500
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With R1, R2 and m defined in the claim, the molecular weight of the capping agent is 208.
Instant claim 1 was amended to recited capping agent having molecular weight of 208 or less. The capping agent as defined cannot have molecular weight less than 208. While applicants had the support for the term “or less” when the first office action was issued, such support is no longer there, since the only two molecular weights utilized by the applicants are 252 and 208.
Consequently, claim 1 is indefinite, since the compound of formula 1 cannot have molecular weight of less than 208.
All dependent claims inherit the deficiencies of instant claim 1.
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.
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 6-14, 16 and 17 are rejected under 35 U.S.C. 102(a)(1) or 102(a)(2) as being anticipated by Tsukamoto (US 2018/0371237).
With respect to claim 1, Tsukamoto discloses carbodiimide based aqueous resin crosslinking agent composition comprising polycarbodiimide(A) and polycarbodiimide (B).
Polycarbodiimide A is synthesized as per Example 1 by reacting HMDI in presence of carbodiimidization catalyst. Resulting polycarbodiimide has polymerization degree ins a range of 3-15 [0069]. The resulting isocyanate terminated polycarbodiimide is then capped with polyethylene glycol monomethyl ether having molecular weight of 500. Consequently, the polycarbodiimide A of Tsukamoto is the same as polycarbodiimide A of the instant invention. See also examples 2, 3, 6 and 7.
Polycarbodiimide B examples 13 and 14 disclose synthesis where HMDI is polymerized in presence of carbodiimidization catalyst. Resulting polycarbodiimide has polymerization degree of 3-20 [0098]. The polycarbodiimide is then end capped with polyethylene glycol monomethyl ether having degree of polymerization in a range of 2-6 [0075] having formula (a2) which is the same type of compound that capped polycarbodiimide A, but with lower polymerization degree.
While the examples disclose PEG monomethyl ether of claim 1 as amended, as it was disclosed above the number of ethylene glycol units is in a range of 2-6. While exemplified MPEG has a molecular weight of 252 where m is 5, Tsukamoto clearly envisaged MPEG having lower molecular weight by defining the integer between 2 and 6 [0072, 0075]. The examples do show enough specificity where the highest molecular weight of terminal group is 300 and lowest is 90. Consequently, MPEG having 4 repeat units is clearly envisaged to meet amended molecular weight. Furthermore, MPEG with m being 5 and MPEG with m being 4 are viewed as homologs.
Additionally, Tsukamoto discloses polyalkylene glycol monoethers such as that utilized in the examples, can have degree polymerization in a range of 2-6 [0075], where picking m as 4 out of 5 possibilities is not a laundry list. It has been held that a prior art genus containing only 20 compounds and a limited number of variations in the generic chemical formula inherently anticipated a claimed species within the genus because "one skilled in [the] art would... envisage each member" of the genus. In re Petering, 301 F.2d 676, 681, 133 USPQ 275, 280 (CCPA 1962)
Here the generic chemical formula is that of polyethylene glycol monomethyl ether, with difference in one repeat unit.
Consequently, while polyethylene glycol monomethyl ether with m integer being 4 is not exemplified, it is clearly envisaged as evidenced in [0075] of Tsukamoto.
With respect to the content of the polycarbodiimides A and B, Tsukamoto teaches that the content of polycarbodiimide A can be 25-70 which means that the polycarbodiimide B would be in a range of 30-75 [0102].
With respect to claims 6 and 7, the invention of Tsukamoto is a carbodiimide based aqueous resin crosslinking agent, which inherently means that the liquid medium is aqueous [0103, 0105], wherein aqueous medium includes water or mixture of water with organic solvent such as methanol, ethanol and the like [0107, 0111].
With respect to claims 8-10, Tsukamoto discloses use of surfactants which include anionic surfactants as preferred embodiment [0121-0123]. Preferred surfactant is dodecylbenzene sulfonate.
With respect to claims 11-13, waterborne resin includes acrylic resins and urethane resins as preferred embodiment [0126-0127].
With respect to claim 14, the composition of Tsukamoto can be used as a coating which meets the limitation of coating and paint [0131-0132]
With respect to claims 16 and 17, coating formed on a substrate is cured film and substrate is an article comprising the cured film [0131-0132].
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Tsukamoto (US 2018/0371237) in view of Nishioka (WO 2017/115804) wherein US 2020/0283639 is used as translation.
The discussion of Tsukamoto from paragraph 1 of this office action is incorporated her by reference. I summary, Tsukamoto discloses carbodiimide crosslinking composition for aqueous coatings.
Tsukamoto discloses the combination of two carbodiimides which are terminated with polyethylene glycol monomethyl ether and are incorporated into coatings to cure resins such as acrylics or urethanes. Tsukamoto does not explicitly disclose that these coatings can be wet-on wet coatings. Tsukamoto other than listing several possible ways a coating can be applied, is not preoccupied with actual method of applying such coating, leaving one of ordinary skill in the art open to determine how to best apply such coating.
Nishioka discloses an aqueous coating composition and a method with which a coating can be applied. Nishioka is very similar to the Tsukamoto because it is also concerned with aqueous coatings.
The coating of Nishioka is urethane or acrylic coating which comprises blocked isocyanate for storage stability and hydrophilicized carbodiimide compound. The carbodiimide has polymerization degree of 1-10 [0109].
The carbodiimide compound [0103] is end capped with hydrophilic group which is polyalkylene glycol monoalkyl ether [0104], wherein molecular weight is in a range of 200-5000 [0107] with the degree of polymerization of 4-20 [0122]. The polyalkylene glycol monoalkyl ether meets the formula of the instant capping agent [0121], wherein in preferred embodiment R4 is hydrogen and R3 includes methyl group [0112]. Production example 5 also discloses use of HMDI isocyanate and polyethylene glycol monomethyl ether as the starting materials of carbodiimide as it is done in Tsukamoto.
Nishioka most importantly discloses a method in which carbodiimide crosslinking agent containing aqueous coatings can be applied. Specifically, in [0192] a substrate is first coated with first layer then with the second layer without any disclosure of drying. Nishioka discloses that the process disclosed therein is wet-on-wet process [0203]. Additionally, applying more than one layer of the composition renders the final article multilayer.
Nishioka further teaches, that coatings applied as wet-on-wet coatings result in coating that have very good gloss and are smooth.
In the light of the above disclosure, it would have been obvious to one having ordinary skill in the art at the time instant invention was filed to apply the coating of Tsukamoto using any known techniques as a wet-on-wet coating. Applying composition of Tsukamoto that includes carbodiimide crosslinking agents and urethane polymer in an aqueous emulsion would also result in composition that after it is coated via wet-on-wet method and allowed to cure by baking has good smoothness and high gloss.
*Note: While examiner did find art to reject claim 15, it should be noted that claims 15 along with claim 14 are claims reciting intended use for the waterborne resin composition. Intended use does not carry patentable weight and claims only have to be capable of performing intended use.
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 KATARZYNA I KOLB whose telephone number is (571)272-1127. The examiner can normally be reached M-F.
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/KATARZYNA I KOLB/Primary Examiner, Art Unit 1767 July 31, 2026
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