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, 22-26, 28, 30-36 and 39 are pending as submitted on 4/29/2026.
Election/Restrictions
Applicant’s election without traverse of Group I, and species wherein the composition comprises TMPTMP (trimethylpropane tris(3-mercaptopropionate)) as the monomer of formula (I) and ASA (allyl succinic anhydride) as the monomer of formula (II), and comprises no third compound in the reply filed on 4/29/2026 is acknowledged.
Claims 20, 22-24, 26, 28, 30-36 and 39 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species or invention, there being no allowable generic or linking claim.
Information Disclosure Statement
The information disclosure statement filed 3/4/2024 fails to comply with 37 CFR 1.98(a)(2), which requires a legible copy of each non-patent literature publication or that portion which caused it to be listed. It has been placed in the application file, but the references which have been struck through have not been considered because no copy of the publication (or portion of the publication which caused it to be listed) has been provided.
Priority
Applicant’s claim for the benefit of prior-filed provisional application 63/127908 under 35 U.S.C. 119(e) is acknowledged. Applicant has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. 119(e) as follows:
The later-filed application must be an application for a patent for an invention which is also disclosed in the prior application (the parent or original nonprovisional application or provisional application). The disclosure of the invention in the parent application and in the later-filed application must be sufficient to comply with the requirements of 35 U.S.C. 112(a) or the first paragraph of pre-AIA 35 U.S.C. 112, except for the best mode requirement. See Transco Products, Inc. v. Performance Contracting, Inc., 38 F.3d 551, 32 USPQ2d 1077 (Fed. Cir. 1994).
The disclosure of the prior-filed application, Application No. 63/127908, fails to provide adequate support or enablement in the manner provided by 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph for one or more claims of this application.
Instant claim 1 recites a composition comprising a first monomer of formula (I) and a second monomer of Formula (II). The examiner is unable to find any disclosure of Formula (I) in the prior filed application. Claim 1 of ‘908 recites “a first monomer comprising at least one thiol group,” but does not limit the structure of the monomer to having an “A” group, or to having 2-6 thiol (SH) groups, as required by instant claim 1. Therefore, the broad recitation of a first monomer in claim 1 of ‘908 does not adequately support the recitation of a monomer of formula (I) as recited in instant claim 1. Claim 6 further limits the first monomer to a species selected from a particular group, however, several polythiol compounds recited in claim 6 (e.g., at least the aromatic species) are not described in the claims or specification of ‘908.
For at least these reasons, claims 1, 4, 6-8 and 25 are not commensurate in scope with the limited support provided in the specification of the provisional application. The present claims therefore describe subject matter that was not presented in the provisional application in such a way as to reasonably convey to one skilled in the relevant art that the inventor(s), at the time the provisional application was filed, had possession of the claimed invention. The claimed subject matter is therefore not considered to be disclosed in the provisional application in the manner provided by 35 USC 112(a), and therefore the claim for priority to the provisional application does not comply with 35 USC 119(e). Therefore, the presently claimed invention can only rely on the filing date of the instant application, which is 12/17/2021.
In the interest of compact prosecution, the following additional differences in scope have been identified between the claims of the instant application and the disclosure in the provisional application:
The instant claims are drawn to a composition comprising a thiol monomer and a second monomer which is either an allyl anhydride or thioester-containing diallyl compound. In contrast, the claims of the provisional application are drawn to a method which includes a step of providing a thiol-ene polymer, wherein the thiol-ene polymer is a reaction product of a thiol monomer and a monomer comprising an anhydride and alkene group. There is no description in the provisional application of a composition of monomers, as recited in the instant claims.
The following monomers recited in instant claim 1 are not described anywhere in the provisional application:
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The following general structure recited in instant claim 1 is not described in the provisional application:
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. The provisional application contains a presentation titled “Background on polymer degradation” which describes species of “thioester-diene” encompassed by the formula, however, there is no disclosure of the generic formula containing X1 and X2 groups, and, the presentation does not describe forming a composition as presently recited.
The range recited in instant claim 4 does not appear to be described in the provisional application.
The ranges recited in claim 8 do not appear to be described in the provisional application. Additionally as to “v)” of claim 8, the provisional application appears to describe viscosities of thiol-ene resins (see Table 1 on p 9), but the examiner is unable to find any description of a viscosity of a composition as presently recited.
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.
Claim 8 is 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.
Claim 8 further limits the composition of claim 1 by requiring at least one of i) through v) to apply to the composition, which indicates that, e.g., claim 8 could be met by satisfying condition (ii) even if none of the other conditions (i), (iii), (iv) or (v) are met.
However, condition (ii) recites an amount of a “second” catalyst. There is no recitation of a “first” catalyst within condition (ii). Therefore, it is not clear whether claim 8 would be met if only a radical initiator or photoinitiator (“second catalyst”) were present with no nucleophilic catalyst (“first catalyst”). That is, it is not clear whether the condition (ii) or condition (iv), which each require a “second catalyst,” could be satisfied if condition (i) is not also satisfied.
Additionally, condition (iv) appears to refer to the second catalyst previously recited in (ii) and the inhibitor previously recited in (iii). However, it is not clear whether the previously recited weight percentages in (ii) and (iii) for each of the referred to components must also be satisfied (i.e., in addition to the recited weight ratio) in order for (iv) to be satisfied. It is therefore unclear whether it is possible to meet claim 8 by satisfying only condition (iv) without also satisfying the preceding conditions (i) through (iii).
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1, 4 and 6-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by 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).
Note: this is a rejection of embodiments encompassed by generic claims; it is not a rejection of the elected species.
As to claims 1, 4 and 6-8, Podgorski discloses thiol-succinic anhydride adducts (abstract), and teaches mixing anhydride and thiol reactants (p 5367, top left). Prior to completion of the reaction to form the adducts thereof, the mixture of reactants is a composition as presently recited. Podgorski discloses allyl succinic anhydride (ASA) as the anhydride reactant, and pentaerythritol tetrakis (3-mercaptopropionate) (PETMP) as the thiol reactant (p 5367, lower right). 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:PETMP of 2:1 and 2:1.5 (p 5367), both of which fall within the range recited in instant claim 4. Podgorski further teaches 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.
Claim(s) 1, 4, 6, 8 and 25 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bowman et al (WO 2018/039331).
Note: this is a rejection of embodiments encompassed by generic claims; it is not a rejection of the elected species.
As to claims 1 and 6, Bowman discloses a composition comprising a multifunctional thioester compound and a multifunctional thiol monomer (see claim 1 on p 82). Bowman discloses an example wherein the thioester compound is TEDAE and the thiol monomer is TMPTMP (see p 78, Table 3).
TEDAE has the following structure (see p 52):
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, which has a structure according to (ii) of instant formula (II), wherein X1 and X2 are both -CH2- and q1 and q2 are both 1.
TMPTMP has a structure according to the fifth species recited in instant claim 6.
Bowman discloses polymerization of thiol monomers (including TMPTMP) with stoichiometric amounts of TEDAE (p 77, lines 25-29), which corresponds to a molar ratio within the range recited in claim 4.
As to claim 8, Bowman exemplifies a composition of TEDAE and PETMP (another thiol encompassed by the instant claims, having a structure according to the sixth compound recited in instant claim 6), wherein nucleophilic catalyst is added in an amount of 3.00 mol% (p 70, example 6) which falls within the range recited in “i)” of claim 8.
As to claim 25, Bowman exemplifies PETMP-TEDAE loaded with silica (example 19, p 79), which corresponds to a filler as presently recited.
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.
Claim(s) 1, 4, 6-8 and 25 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 Bowman et al (WO 2018/039331).
This is a rejection of the elected species wherein the first monomer is TMPTMP and the second monomer is ASA.
As to claims 1, 6 and 7, 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 ASA as the anhydride and PETMP as the thiol (p 5367), and teaches mixing anhydride and thiol reactants (p 5367, top left). Prior to completion of the reaction to form the adducts thereof, the mixture of reactants is a composition as presently recited.
Podgorski fails to teach other thiol monomers which can be used to form the CANs, and therefore 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). 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 taught by 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 Podgorski’s composition.
As to claims 4 and 8, 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. Bowman also discloses polymerization of thiol monomers (including TMPTMP) with stoichiometric amounts of TEDAE (p 77, lines 25-29), which corresponds to a molar ratio within the range recited in claim 4. Podgorski further teaches 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. Bowman similarly exemplifies a composition of TEDAE and PETMP wherein nucleophilic catalyst is added in an amount of 3.00 mol% (p 70, example 6) which falls within the range recited in “i)” of claim 8.
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.
Conclusion
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766
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