DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 9, 10, 13, 14, 16-20 and 22 are pending as amended on 6/12/2026. Claims 17-20 and 22 stand withdrawn from consideration.
The rejections set forth below have been modified to reflect that the claims have been amended to no longer recite the presence of water in the reacting step, and, to reflect that the stain resistance property has been amended to require using “a red dye stain.” These modifications to the rejection of record were necessitated by amendment, and therefore, this action is properly made final. Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. 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 Rejections - 35 USC § 103
Claim(s) 9, 10, 13, 14 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Tachibana et al (US 6169161) in view of Zhang et al (US 2017/0183796).
As to claims 9, 10, 13 and 14, Tachibana discloses a process for producing polyamides from caprolactam as the essential ingredient (col 3, lines 55-59). Tachibana discloses that when monocarboxylic acids and/or monoamines are used for end-capping, the terminal group concentration of the polyamide is lower than that of the non-end-capped polyamide (col 7, lines 31-36). Tachibana names acetic acid (col 7, line 43) and cyclohexylamine (col 7, line 67) among examples of carboxylic and amine end-capping compounds, and teaches that the end-capping agent can be added along with the caprolactam in the initial stage of polymerization (col 8, lines 41-45).
Tachibana teaches that depending on the use of the polyamide, the terminal group concentration could be well controlled, and that both terminal amino and terminal carboxyl group concentrations preferably fall between 1.0x10-5 and 15.0x10-5 eq/g (col 8, lines 33-38), which is equivalent to 10-150 mmol/kg (
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); therefore, the ranges of unterminated amine and carboxyl end group concentrations taught by Tachibana overlap the presently claimed ranges of “less than 20 mmol/kg.”
Arriving at the presently claimed method from Tachibana’s disclosure requires choosing to utilize both a monocarboxylic end-capping compound (acetic acid) and a monoamine end-capping compound (cyclohexylamine) from Tachibana’s lists of suitable examples thereof, and, requires selecting a terminal amino group concentration and a terminal carboxyl group concentration from within Tachibana’s disclosed range which falls within the presently claimed range.
Tachibana teaches that terminal amino group concentration is preferred to be higher when dyability of fibers is desired to increase, and preferred to be lower to prevent discoloration or gelling under long-term aging conditions. Tachibana further teaches that it is desirable for both terminal carboxyl and terminal amino group concentration to be lower to prevent breakage in melt-spinning the polyamide (col 8, lines 16-35). Similarly, Zhang discloses polyamides which have dual termination of amino and carboxyl end groups, and which is useful in producing textiles [0006]. Zhang teaches that mono-terminated polyamide-6 may increase in viscosity prior to being extruded from a spinneret, which impacts spinnability and shortens spin pack life of the material. Zhang teaches that the deleterious effects are especially seen in high-speed spinning applications, such as for textiles [0004]. Zhang therefore teaches [0047] dual-terminated polyamide resin produced by adding two separate terminators during the polyamide polymerization. An acidic terminator is used to terminate the NH2 amine end groups, and an amine terminator is used to terminate the -COOH carboxyl end groups of PA-6 resin.
Considering the disclosures of Tachibana and Zhang as discussed above, the person having ordinary skill in the art would have been motivated to include both an amine end-capping compound and a carboxyl end-capping compound when polymerizing caprolactam in order to decrease the concentrations of both amino and carboxyl end groups, thereby achieving a desired degree of dyeability, and a desired degree of stability and breakage prevention when melt spinning. It would have been obvious to the person having ordinary skill in the art, therefore, to have end-capped polyamide with a monoamine and a monocarboxylic acid, as taught by Tachibana, by selecting any appropriate monoamine from those named by Tachibana (including cyclohexylamine) and any appropriate monocarboxylic acid from those named by Tachibana (including acetic acid). Case law has established that it is prima facie obvious to choose from a finite number of identified, predictable solutions with a reasonable expectation of success. KSR Int'l Co. v. Teleflex, Inc., 550 U.S. 398 (2007). MPEP 2143, rationale (E).
Additionally, the person having ordinary skill in the art would have been motivated to decrease the concentration of both unterminated amine and carboxyl groups for applications requiring decreased dyability of fibers, and, in order to prevent breakage during melt-spinning of polyamide. It would have been obvious to the person having ordinary skill in the art, therefore, to have selected any appropriate terminal amino and carboxyl group concentrations within Tachibana’s disclosed range of 10-150 mmol/kg, including concentrations within the presently claimed range of less than 20 mmol/kg (or between 8-20 mmol/kg as in claim 13, or 6-20 mmol/kg as in claim 14), in order to achieve desired properties depending on the use of the polyamide.
As to the presently recited viscosity:
Tachibana teaches that the relative viscosity of the final polyamide in sulfuric acid falls between 2.2 and 6.0, and that if smaller than 2.2, the polyamide does not exhibit the intended mechanical properties, but if larger than 8.0, the melt viscosity is so high that molding is difficult (col 7, lines 22-30). Tachibana fails to disclose the corresponding formic acid viscosity of the polyamide.
Zhang teaches a relative viscosity (RV) as little as 2.4, or a higher RV of 2.7 to 3.0, corresponding to a higher molecular weight and improved dimensional stability [0051]. Zhang’s disclosed RV range falls within the RV range disclosed by Tachibana. Zhang further teaches that the formic acid viscosity (FAV) of the polyamide is 35-65 according to ASTM D-789 [0052]. Given that Tachibana’s disclosed RV range encompasses the RV values taught by Zhang, there is reasonable basis to conclude that the range of RV values taught by Tachibana converts to a range of formic acid viscosity values which similarly encompasses the formic acid viscosity values taught by Zhang. There is reasonable basis to conclude, therefore, that Tachibana’s disclosed range of RV values corresponds to a range of FAV values which encompasses the presently claimed range of 40-90. It would have been obvious to the person having ordinary skill in the art, therefore, to have prepared a polyamide, as suggested by modified Tachibana, by selecting any appropriate RV within Tachibana’s disclosed range of 2.2-6.0 in order to achieve a desired balance between mechanical properties and moldability, including an RV corresponding to a FAV within the presently claimed range.
As to the presently recited spinning speed:
As discussed above, Tachibana teaches that it is desirable for both terminal carboxyl and terminal amino group concentration to be lower to prevent breakage when melt-spinning the polyamide (col 8, lines 16-35). However, Tachibana fails to teach a spinning speed for fiber formation. Zhang teaches that mono-terminated polyamide-6 may increase in viscosity prior to being extruded from a spinneret, which impacts spinnability and shortens spin pack life of the material. Zhang teaches that the deleterious effects are especially seen in high-speed spinning applications, such as for textiles [0004]. Zhang teaches spinning the dual-terminated polyamide “at relatively high speeds,” for example, within a range of 3500-6000 m/min [0065].
Considering Zhang’s disclosure, one having ordinary skill in the art would have recognized that spinning speeds of 3500-6000 m/min were known in the art as effective for providing a desired textile product from molten polyamide. Furthermore, given that modified Tachibana suggests dual-terminated polyamides having even lower amino and carboxylic end group concentrations than disclosed by Zhang, one would have recognized that modified Tachibana suggests polyamides which are even less susceptible to melt viscosity increase than the polyamides disclosed by Zhang. Therefore, one having ordinary skill in the art would have had a reasonable expectation that Zhang’s “high-speed” fiber spinning speeds could be successfully utilized for spinning the polyamide of modified Tachibana without seeing deleterious effects due to increase in viscosity during spinning. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a fiber from polyamide, as suggested by modified Tachibana, by selecting any appropriate spinning speed within a range of 3500-6000 m/min, as disclosed by Zhang, in order to effectively produce a textile from the polyamide. (As to claim 10, it would have been obvious to the person having ordinary skill in the art to have formed a fiber from the polyamide suggested by modified Tachibana by utilizing any high-speed spinning speed within Zhang’s range of 3500-6000 m/min, including a speed within the presently claimed range of 2500-5000 m/min, in order to effectively produce a textile from the polyamide. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.)
As to the presently recited stain resistance:
Tachibana fails to disclose the presently recited ΔE property, which is a measure of red dye stain resistance. However, as evidenced by the instant specification (see [0076]), red dye stain resistance improves as AEG and CEG (particularly AEG) of polyamide decrease. Given that modified Tachibana suggests decreasing the AEG and CEG of polyamide in order to improve melt stability, including to values within the claimed ranges, there is reasonable basis to conclude that modified Tachibana suggests polyamides having improved stain resistance, including red dye stain resistance corresponding to ΔE within the presently claimed range.
As to claim 16, Tachibana teaches a polyamide having an unreacted caprolactam content from 0 to 0.5 wt% and an oligomer content from 0 to 1.25 wt% (col 3, lines 4-8). Zhang similarly teaches an extractable content which is less than 0.6 wt% [0054]. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed polyamide fiber, as suggested by modified Tachibana, by selecting any appropriately low content of extractables (caprolactam, oligomer) within the ranges taught by Tachibana and Zhang, including within the presently claimed range of 1.0 wt% or less, in order to provide a material having a quality suitably high for the applications taught by Tachibana in col 1, lines 14-20.
Response to Arguments
Applicant's arguments filed 6/12/2026 have been fully considered.
Applicant argues (p 7 and p 9) that Tachibana teaches terminators as being optional in nature, and teaches terminating amine or carboxyl end groups, but not both. However, Tachibana discloses: “When monocarboxylic acids and/or monoamines are used for the end-capping, the terminal group concentration of the polyamide is lower than that of the non end-capped polyamide” (emphasis added). In view of the “and/or” in the sentence copied above, the examiner maintains that one having ordinary skill in the art would have envisaged three end-capping embodiments from Tachibana’s disclosure: the use of monocarboxylic acids with no monoamines, the use of monoamines with no monocarboxylic acids, and, the use of both monocarboxylic acids and monoamines. Therefore, Applicant’s argument that Tachibana does not teach terminating both amine and carboxyl end groups is not persuasive.
Applicant argues (p 7, last paragraph and p 10, first paragraph) that in view of the number of possible combinations of carboxylic and amine compounds taught by Tachibana, and the fact that Tachibana contains no examples of dual-terminated polyamide, arriving at the presently claimed combination of acetic acid as the monocarboxylic acid compound and cyclohexylamine as the monoamine compound is undue experimentation against the teachings of Tachibana. However, disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (MPEP 2123). Moreover, the fact that Tachibana discloses numerous types of monocarboxylic compounds and numerous types of monoamine compounds which can be suitably selected for endcapping terminal groups does not render any particular combination of monocarboxylic compound and monoamine compound less obvious. A reference is available for all that it teaches to a person of ordinary skill in the art. Merck & Co., Inc. v. Biocraft Laboratories, Inc. 874 F.2d 804, 807 (Fed. Cir. 1989). Applicant has not established any unexpected or unpredictable result associated with the selection of acetic acid as monocarboxylic compound and cyclohexylamine as monoamine compound.
Applicant argues (p 8 and p 9) that Tachibana’s examples do not support the lower end of the AEG and CEG ranges disclosed by Tachibana, and therefore, the overlap between the prior art range and the claimed range requires selection of values that are not exemplified. However, as discussed above, disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (MPEP 2123). Applicant has not established any unexpected or unpredictable result associate with the claimed ranges of AEG and CEG values, and therefore, a prima facie case of obviousness exists as set forth in the rejection of record.
Applicant argues (p 11) that RV and FAV are measured under different methodologies and solvent systems and are not directly interchangeable, and therefore Zhang’s RV and FAV values would not be assumed to be applicable to Tachibana. However, the rejection of record does not take the position that any polymer species having the RV range taught by Zhang (and Tachibana) would necessarily also have an FAV within Zhang’s disclosed range. Both Tachibana and Zhang disclose polymers having the same backbone structure - polycaprolactam (PA-6). Zhang discloses, and modified Tachibana suggests, PA-6 having dual-termination of both amine and carboxylic end groups. The rejection of record lays out the substantial similarities between the dual-terminated PA-6 suggested by modified Tachibana and the dual-terminated PA-6 taught by Zhang, and concludes that for a dual-terminated PA-6 as suggested by modified Tachibana, the range of RV values taught by Tachibana must correspond to a range of FAV values which encompasses FAV values taught by Zhang (because, the range of RV values taught by Zhang falls within the range of RV values taught by Tachibana). Applicant has not provided any reasoning or evidence which rebuts the finding that the wide range of PA-6 RV values taught by Tachibana corresponds to a range of PA-6 FAV values which at least overlaps the claimed range.
Applicant argues (pp 11-12) that Zhang’s disclosed spinning speeds are tied to its own dual-terminated system which are optimized for high-speed performance, and therefore it cannot be assumed that modified Tachibana’s composition could be spun under the same conditions disclosed in Zhang. However, Applicant’s argument is unpersuasive because it does not appear to consider the discussion set forth in paragraph 27 of the previous action, which finds that because “modified Tachibana suggests dual-terminated polyamides having even lower amino and carboxylic end group concentrations than disclosed by Zhang, one would have recognized that modified Tachibana suggests polyamides which are even less susceptible to melt viscosity increase than the polyamides disclosed by Zhang. Therefore, one having ordinary skill in the art would have had a reasonable expectation that Zhang’s “high-speed” fiber spinning speeds could be successfully utilized for spinning the polyamide of modified Tachibana without seeing deleterious effects due to increase in viscosity during spinning.”
Applicant argues (p 12) that the recited testing method conforms to a specific, standardized testing protocol, the AATCC Test Method 175-08 (i.e., the 2008 version of the AATCC TM175), which defines a performance that must be demonstrated under defined conditions. Applicant has not indicated whether the “red dye stain testing” conditions described for instant example 3 (spec [0072-3]) are the same as the AATCC TM 175-08 test protocol conditions, nor whether the test protocol used to obtain stain resistance values for fibers in Table 6 on page 17 of the instant spec are the same as the conditions defined in [0072-73] for testing pellets, and/or, the same as defined in the standard AATCC TM175-08 test protocol conditions. Regardless, the assertion that the recited property merely defines a capability has been deleted from the rejection of record. The rejection is maintained for reasoning which remains unchanged: as evidenced by the instant specification (see [0076]), stain resistance improves as AEG and CEG (particularly AEG) of polyamide decrease. Given that modified Tachibana suggests decreasing the AEG and CEG of polyamide in order to improve melt stability, including to values within the claimed ranges, there is reasonable basis to conclude that modified Tachibana suggests polyamides having improved stain resistance, including stain resistance corresponding to ΔE within the presently claimed range. Applicant argues (p 13) that the conclusion that the claimed ΔE property would inherently result is not supported by the cited references. However, the rejection of record establishes the obviousness of decreasing the AEG and CEG of Tachibana’s polyamide within Tachibana’s disclosed ranges, and Applicant has not provided any reasoning or evidence which rebuts the finding that stain resistance improves (ΔE decreases) as AEG and CEG decrease, including to ΔE within the claimed range.
Conclusion
Applicant's amendment necessitated the modified 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766
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