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 1, 4, 6-8, 20, 23-26, 28, 30-36, 39 and 40 are pending as amended on 8/17/2026. Claims 20, 23-24, 26, 28, 30-36 and 39 stand withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species or invention, there being no allowable generic or linking claim.
The new grounds of rejection below were necessitated by Applicant’s amendment to claim 1 which adds limitations to claim 1, and by Applicant’s amendment to add new claim 40. 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Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn.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) 1, 4, 6-8 and 40 is/are rejected under 35 U.S.C. 103 as being unpatentable over Podgorski et al (Mixed mechanisms of bond exchange in covalent adaptable networks: monitoring the contribution of reversible exchange and reversible addition in thiol–succinic anhydride dynamic networks, Polym. Chem., 2020, 11, 5365; publication date 31 March 2020) in view of Fong et al (US 2017/0291357).
Podgorski discloses covalent adaptable networks (CANs) which combine attributes of thermoplasticity such as pliability and processability with thermosets thermomechanical and dimensional stability (p 5365, left column). Podgorski discloses that thiol-anhydride-based CANs exhibit an extraordinary reversibility of the thioester-anhydride linkage (p 5366, right column), and provides a study of the properties of thiol-succinic anhydride photopolymer CANs (conclusion, p 5375). Podgorski teaches that a thiol-thioester exchange contributes to the overall exchange dynamics (p 5375, conclusion). Podgorski discloses photopolymer networks formed from allyl succinic anhydride (ASA) as the anhydride reactant, and pentaerythritol tetrakis (3-mercaptopropionate) (PETMP) as the thiol reactant (p 5367, lower right). Podgorski shows that the CANs are formed via ASA and tetrathiol ring-opening reactions coupled with thiol-ene polymerization (Scheme 1, p 5366).
The tetrathiol, PETMP, has a structure according to instant formula (I) wherein n is 4, and is the sixth structure in the group recited in instant claim 6 (See Scheme 1, p 5366, top right). ASA is the monomer recited in instant claim 7. Podgorski discloses molar ratios of ASA:thiol of 2:1 and 2:1.5 (p 5367), both of which fall within the range recited in instant claim 4. Podgorski further teaches including DMAP (a nucleophilic catalyst) in an amount of 5 mol% (see fig 6 on p 5373, (c) and (d)), which falls within the range recited in “i)” of claim 8, and teaches including DMPA (a radical photoinitiator, see p 5366 lower left) in an amount of 0.2 wt% (see p 5367, upper left), which falls within the range recited in claim 40.
Podgorski teaches that the CANs are envisioned to enable new and previously unattainable applications in 3D printing fields (p 5365, right). However, Podgorski fails to teach including a radical inhibitor, and fails to teach a viscosity as presently recited.
Fong discloses inks for use with 3D printing systems [0002] which comprises a thiol monomer component and an ethylenically unsaturated monomer component, which react with one another in a thiol-ene reaction [0007]. Among suitable thiol monomers, Fong discloses PETMP [0030] (i.e., the same tetrathiol taught by Podgorski). Fong teaches that a “single ink” (wherein the thiol and ene monomers are combined prior to printing) may be used if conditions disfavoring premature reaction of the ink components, such as by including a polymerization inhibitor, are present [0011,12].
Fong teaches that any polymerization inhibitor may be used, and that it can retard, decrease, or prevent polymerization from occurring for some period of time. Fong names MEHQ (which is a radical inhibitor as presently recited) as a suitable polymerization inhibitor [0053], and further teaches that BHT (another type of radical inhibitor) can be used [0054]. Fong teaches that an inhibitor is present in an ink in an amount ranging from 0.01 to 2 wt% [0055]. Considering Fong’s disclosure, it would have been obvious to the person having ordinary skill in the art to have combined any appropriate amount (within Fong’s range of 0.01 to 2 wt%) of Fong’s radical polymerization inhibitor (such as MEHQ or BHT) with a composition comprising ASA and PETMP, as taught by Podgorki, in order to prevent premature polymerization of the components such that the composition can be used as a single ink for 3D printing, including an amount within the presently claimed range of 0.005 to 0.5 wt%.
Podgorski further fails to teach a viscosity as presently recited.
Fong teaches that a “monomeric” monomer has a viscosity of 500 cP or less, while an oligomeric monomer has a viscosity of 1000 cP or more [0035]. Modified Podgorski teaches a monomeric composition having the same monomeric components as claimed and described in the instant specification. Considering that compositions which comprise substantially the same components must have substantially the same viscosity, there is reasonable basis to conclude that modified Podgorski suggests a monomeric composition which has substantially the same viscosity as the instant compositions, i.e., within the presently claimed range.
Alternatively, Fong teaches that an ink, when non-cured, has a viscosity profile consistent with the requirements and parameters of one or more 3D printing systems, and teaches a dynamic viscosity ranging from 8.0 cP to 14.0 cP (equivalent to 8.0 to 14.0 mPa.s) at a jetting temperature [0071]. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed Podgorki’s composition having a viscosity (as measured at any appropriate shear rate, including 200 s-1) within Fong’s disclosed range in order to meet the requirements and parameters of 3D printing systems.
Claim(s) 1, 4, 6-8, 25 and 40 is/are rejected under 35 U.S.C. 103 as being unpatentable over Podgorski et al (Mixed mechanisms of bond exchange in covalent adaptable networks: monitoring the contribution of reversible exchange and reversible addition in thiol–succinic anhydride dynamic networks, Polym. Chem., 2020, 11, 5365; publication date 31 March 2020) in view of Fong et al (US 2017/0291357), and further in view of Bowman et al (WO 2018/039331).
The rejection over Podgorski in view of Fong above is incorporated by reference.
As to the elected species:
Podgorski fails to teach other thiol monomers which can be used to form the CANs, and therefore modified Podgorski fails to teach utilizing TMPTMP instead of PETMP.
Like Podgorski, Bowman teaches thioester-containing CANs (p 1) which react via thiol-thioester exchange (p 14, lines 6-11), and which are suitable for use in 3D printing applications (p 46, line 2). Bowman discloses CANs formed from a composition which comprises a thioester monomer comprising alkene end groups (see example monomers on pp 32-33, as well as examples wherein the thioester compound is TEDAE, which has the following structure (see p 52):
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. Bowman further discloses several suitable multifunctional thiol monomers (p 34), including PETMP (a tetrathiol) and TMPTMP (a trithiol). See p 34, lines 8-10).
Bowman teaches that network structures are readily adjustable by simple changes to monomer structures, and therefore material properties are precisely tunable. Bowman provides examples comparing the properties of network structures, wherein various polythiol monomers are polymerized with TEDAE. The examples show that the functionality of the thiol monomer affects polymer properties. Bowman teaches that trithiol TMPTMP, tetrathiol PETMP and hexathiol di-PETMP are structurally similar, and that they generate networks with small increases in Tg and rubbery moduli (example 16, pp 77-78, and Table 3 on p 78). Bowman teaches that altering one of the two reactive components in the network enables the design of thiol-ene polymers for a range of particular material applications (p 78, lines 10-11).
Considering Bowman’s disclosure, when forming CANs from a polythiol as a reactive component, the person having ordinary skill in the art would have been motivated to change the functionality of the thiol monomer (such as by substituting TMPTMP for PETMP) in order to tune properties such as Tg and rubbery modulus as required for a particular material application. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a composition for preparing a CAN from ASA and a thiol, as suggested by modified Podgorski, by substituting the tetrathiol taught by Podgorski (PETMP) for a structurally similar trithiol (TMPTMP), as taught by Bowman, in order to tune the properties of the CAN ultimately obtained from modified Podgorski’s composition.
As to claim 25, Podgorski fails to teach including a filler. However, Bowman teaches that filler-reinforced composites are commonly employed with photopolymers in order to obtain enhanced mechanical properties, and exemplifies utilizing silica as a filler (example 19, p 79). It would have been obvious to the person having ordinary skill in the art, therefore, to have included silica in a composition as suggested by modified Podgorski (i.e., a composition of ASA and TMPTMP) in order to provide a composite having enhanced mechanical properties.
Response to Arguments
Applicant's arguments filed 8/17/2026 have been fully considered.
Regarding the priority claim, Applicant argues (pp 10-11) that the provisional application identifies the same invention and elected chemistry under examination, citing disclosures of ASA and TMPTMP in the provisional application. However, as set forth in detail in the discussion in paragraphs 9-11 of the previous action, the scope of the instant claims is not commensurate in scope with the description and claims provided in the provisional application. For at least the reason that none of the instant claims are limited to a composition which is described in the provisional application (e.g., a composition comprising ASA and TMPTMP as monomers), there is no claim which has complied with the conditions for receiving the benefit of the earlier filing date under 35 USC 119(e).
Applicant’s arguments (pp 11-13) that the rejections under 35 USC 112, 102 and 103 have been overcome by amendment are persuasive. However, the claims are not presently in condition for allowance in view of the new rejections set forth above.
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.
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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