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 .
Election/Restrictions
Claims 113-118 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 23 April 2025.
Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i).
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 99-101,103-104,107,110, and 112 is/are rejected under 35 U.S.C. 103 as being unpatentable over Rao et al. (US 2020/0317917).
Regarding Claim 99, Rao et al. (US’917) teach a composition comprising: a thiol-functional prepolymer [0006,0042,0046]; a polyalkenyl [0006]; a crosslinker comprising a polyepoxide [0046,0551,0631,0686]; and a free radical polymerization initiator [0080,0083,0243,0292,0627,0006]. US’917 fails to teach the recited thiol functionality. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the thiol functional cross linker with the recited level of functionality to achieve a desirable crosslink density.
Regarding Claim 100, US’917 teaches 45-70 wt. % of thiol-terminated sulfur-containing (i.e. thioether, also sulfide) prepolymer [0090,0092,0046,0732]; 1-10 wt. % polyalkenyl [0551,0732]; 1 wt % to 3 wt %, or from 1.5 wt % to 2.5 wt % of a free radical polymerization initiator (organoborane complex, [0624,0626,0732]). US’917 fails to teach 0.01-15 wt% of crosslinker. US’917 teaches an organoborane-amine complex [0630], including polyamine [0631], and a cross-linking density of 0-2% [0388-0389]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 by providing crosslinker in a concentration within the recited range through routine optimization, because US’917 both teaches the claimed crosslinker and suggests the degree of desirable crosslinking density. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 101, US’917 teaches that the thiol-functional prepolymer comprises a thiol-functional sulfur-containing prepolymer (i.e. thioether, also sulfide) [0044,0046,0090,0092].
Regarding Claim 103, US’917 teaches that the composition can include polyamine or polyepoxide as curing agents/crosslinking agents [0040,0044,0046,0686,0630-0631,0679] without teaching a specific ratio of the combination. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 by using both polyamine and polyepoxide as curing/ crosslinking linking agents, since US’917 teaches that each performs this function. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 104 teaches that the free radical polymerization initiator comprises an organic peroxide or an actinic radiation (e.g. ultraviolet light)-activated free radical photoinitiator [0050,0081,0243,0646].
Regarding Claim 107, US’917 teaches triethylamine and diethylenetriamine [0243,0635].
Regarding Claim 110, US’917 teaches that the composition can include a polyepoxide crosslinker and a tertiary amine base (e.g. triethylamine and diethylenetriamine [0044,0243,0635,0686].
Regarding Claim 112, US’917 teaches that the thiol-functional prepolymer can comprise a thiol-functional polythioether [0090] and that the polyalkenyl can comprise a bis(alkenyl)ether [0367].
Claim(s) 105-106,108, and 111 is/are rejected under 35 U.S.C. 103 as being unpatentable over Rao et al. (US 2020/0317917) in view of Liu et al. (WO 2018/227149).
Regarding Claim 105, US’917 fails to teach a transition metal. WO’149 is analogous art, which teaches a composition comprising: a thiol-functional prepolymer; a polyalkenyl [0006]; a crosslinker comprising a polyamine, a polyepoxide, or a combination thereof [0046,0551,0631,0686]; and a free radical polymerization initiator [0080,0083,0243,0292,0627,0006]. In addition, it teaches that the composition comprises a transition metal (e.g. cobalt, copper, manganese, iron, vanadium) complex (Abstract; [0496]) to improve a depth of sealing with the composition [0002,0024]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 with a transition metal complex, because WO’149 suggests that a transition metal complex in the composition of US’917 improves a cure depth of sealant compositions.
Regarding Claim 106, WO’149 teaches that the composition comprises from 0.01 wt% to 3 wt% of the transition metal complex, wherein wt% is based on the total weight of the composition [0504]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 with a transition metal complex, because WO’149 suggests that the recited concentration range of a transition metal complex in the composition of US’917 improves a cure depth of sealant compositions. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 108, US’917 fails to teach the recited range of concentration. WO’149 teaches that the composition comprises from 0.01 wt% to 2 wt% of the tertiary amine base to reduce tack free time [0515], wherein wt% is based on the total weight of the composition (Claim 14). It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 with a tertiary amine base in the recited concentration, because WO’149 suggests this concentration to reduce tack time. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 111, US’917 fails to teach the recited concentration of tertiary amine base. WO’149 teaches a polyepoxide crosslinker [0590] and 0.01 to 2 wt % of tertiary amine base [0515,0519-0520] to reduce tack free time [0515], wherein wt% is based on the total weight of the composition (Claim 14). It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 with a tertiary amine base in the recited concentration, because WO’149 suggests this concentration to reduce tack time. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Claim(s) 99-101, 103-108, and 110-112 are is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (WO 2018/227149).
Regarding Claim 99, Liu et al. (WO’149) teaches a composition comprising: a thiol-functional prepolymer [0006]; a polyalkenyl [0156]; a crosslinker comprising a polyamine [0070] or a polyepoxide [0590]; and a free radical polymerization initiator (Abstract; [0104]). WO’149 fails to teach the recited level of thiol functionality. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the thiol functional cross linker with the recited level of functionality to achieve a desirable crosslink density.
Regarding Claim 100, WO’149 teaches 46-54 wt. % of thiol-terminated sulfur-containing (i.e. thioether, also sulfide) prepolymer [0110]; 1-10 wt. % polyalkenyl [0424]; 0.01-2 wt% of a free radical polymerization initiator [0649]. WO’149 fails to teach 0.01-15 wt% of crosslinker. WO’149 teaches polyamine curing agent/ crosslinker and a cross-linking density of 0-2% [0518, 0062,0068-0070]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of WO’149 by providing crosslinker in a concentration within the recited range through routine optimization, because WO’149 both teaches the claimed crosslinker and suggests the degree of desirable crosslinking density. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 101, WO’149 teaches a thio-functional sulfur-containing prepolymer (e.g. thioether, also sulfide) [0068,0086,0108].
Regarding Claim 103, WO’149 teaches that the composition can include polyamine or polyepoxide as curing agents/crosslinking agents [0062,0068-0070,0590] without teaching a specific ratio of the combination. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of WO’149 by using both polyamine and polyepoxide as curing/ crosslinking linking agents, since WO’149 teaches that each performs this function. Also, generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical.
Regarding Claim 104, WO’149 teaches that the free radical polymerization initiator comprises an organic peroxide free radical polymerization initiator, also an actinic radiation-activated (ultraviolet light) free radical photoinitiator (Abstract; Fig. 1; [0103-0105]).
Regarding Claim 105, WO’149 teaches that the composition comprises a transition metal (e.g. cobalt, copper, manganese, iron, vanadium) complex (Abstract; [0496]).
Regarding Claim 106, WO’149 teaches that the composition comprises from 0.01 wt% to 3 wt% of the transition metal complex, wherein wt% is based on the total weight of the composition [0504].
Regarding Claim 107, WO’149 teaches that the composition comprises a tertiary amine base [0515,0519-0520].
Regarding Claim 108, WO’149 teaches that the composition comprises from 0.01 wt% to 2 wt% of the tertiary amine base, wherein wt% is based on the total weight of the composition (Claim 14).
Regarding Claim 110, WO’149 teaches that the composition can include a polyepoxide crosslinker and a tertiary amine base (Claim 14; [0590,0515,0519,0802]).
Regarding Claim 111, WO’149 teaches a polyepoxide crosslinker [0590] and 0.01 to 2 wt % of tertiary amine base [0515,0519-0520].
Regarding Claim 112, WO’149 teaches that the thiol-functional prepolymer comprises a thiol-functional polythioether [0068,0086,0108]; and the polyalkenyl comprises a bis(alkenyl) ether [0156,0422].
Claim(s) 102 is/are rejected under 35 U.S.C. 103 as being unpatentable over Rao et al. (US 2020/0317917) in view of Cui et al. (US 2020/0283663).
Regarding Claim 102, US’917 teaches that the polyalkenyl can comprise a bis(alkenyl)ether [0555] and that the curing agent can be polyepoxide (see rejection of Claim 99 above) or polyamine, which can comprise a cycloaliphatic polyamine (e.g. isophorone diamine) [0631]. US’917 fails to explicitly teach a combination of polyepoxide and polyamine. However, it would have been obvious to mix the two compounds, each having the same function as crosslinker (“curing” includes “crosslinking” in US’917 [0040,0044]), to provide the same function as a mixture. US’917 fails to teach a difunctional polyepoxide. Cui et al. (US’663) is analogous art in the field of an analogous compositions, including a combination of thiol-functional prepolymer, polyalkenyl, polyepoxide crosslinker/curing agent, and free radical polymerization initiator [0038,0470,0529,0218]. Additionally, US’663 teaches a difunctional polyepoxide curing agent [0737]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of US’917 with a combination of cycloaliphatic polyamine and difunctional polyepoxide, because US’917 teaches curing agents, including cycloaliphatic polyamines and polyepoxides, while US’663 provides more detail about polyepoxide curing agents and suggests in particular difunctional polyepoxides for an analogous composition.
Claim(s) 102 is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (WO 2018/227149) in view of Cui et al. (US 2020/0283663).
Regarding Claim 102, WO’149 teaches that the polyalkenyl can comprise a bis(alkenyl)ether [0555] and that the curing agent can be polyepoxide (see rejection of Claim 99 above) or a polyamine, and that the polyamine can comprise a cycloaliphatic polyamine [0437,0518]. US’917 fails to explicitly teach a combination of polyepoxide and polyamine. However, it would have been obvious to mix the two compounds, each having the same function as crosslinker (“curing” includes “crosslinking” in US’917 [0040,0044]), to provide the same function as a mixture. WO’149 fails to teach a difunctional polyepoxide. US’663 is analogous art in the field of an analogous compositions, including a combination of thiol-functional prepolymer, polyalkenyl, polyepoxide crosslinker/curing agent, and free radical polymerization initiator [0038,0470,0529,0218]. Additionally, US’663 teaches a difunctional polyepoxide curing agent [0737]. It would have been obvious to a person of ordinary skill in the art at the time of invention to modify the composition of WO’149 with a combination of cycloaliphatic polyamine and difunctional polyepoxide, because WO’149 teaches curing agents, including cycloaliphatic polyamines and polyepoxides, while US’663 provides more detail about polyepoxide curing agents and suggests in particular difunctional polyepoxides for analogous compositions.
Response to Arguments
Applicant's arguments filed 23 June 2026 with respect to the rejections of Claims 99-108 and 110-112 under 35 USC 102 and 103 have been fully considered but they are not persuasive.
In response to Applicant’s argument concerning average thiol-reactive functionality (Remarks, pp. 5-8), this argument was answered in the previous Office Action at p. 6. A crosslinker functions by cross-links forming between functional groups of the crosslinker and reactive groups of another species -- this is how crosslinks form. US’917 suggests polyepoxide curing agents as a component along with thiol-terminated polythioether prepolymer [0686]. Additionally, it incorporates US Pat. No. 8,993,691, which further explains the relationship of functional groups of crosslinkers to functional groups of polymers with which the functional groups of crosslinkers are reactive. Moreover, Rao suggests a crosslinker density of 0 to 2.0% with a thiol-terminated prepolymer [0388], which would have suggested a crosslinker with a sufficient number of functional groups to provide a desirable cross-linking for a given intended use. Thus, Applicant’s arguments are not persuasive.
Similarly, Liu (WO’149) (Remarks, pp. 8-9) teaches a thiol-terminated prepolymer and a cross-linking density from 0% to 2% [0366] and also suggests a polyepoxide curing agent [0590], also incorporating US Pat. No. 8,993,691, if the relationship of crosslinker functionality to polymer group functionality is in doubt.
In response to Applicant’s argument concerning Claim 102 and the obviousness of selecting a difunctional polyepoxide among polyepoxides taught in [0737] (Remarks, p. , it is not clear what Applicant means by “Cui’s broader list of polyepoxide curing agent options.” Cui describes a polyepoxide curing agent that “can include a combination of difunctional polyepoxides, trifunctional polyepoxides, small molecule polyepoxides, and epoxy-terminated prepolymers. Therefore, without the benefit of further explanation of what Applicant considers Cui’s “broader list” it is not clear whether Applicant means that Cui teaches curing agents other than the combination taught in [0737] or whether he is mistakenly characterizing the combination of components as a list of separate curing agents. Because Applicant cites only paragraph [0737] for the proposition that there is a broader list, the argument seems be interpreting the combination of components of a curing agent as a list of crosslinkers. At any rate, starting with art teaching an aliphatic diamine crosslinker for a curable/ crosslinkable polymer (Rao) and a multi-component polyepoxide crosslinker, including difunctional polyepoxide (Cui), for the same or analogous curable/crosslinkable polymer, it would have been obvious to combine them as components of a crosslinker for the curable/ crosslinkable polymer with the expectation of crosslinking the curable/crosslinkable polymer for an intended use (not required of the composition). Moreover, Cui et al. provides further evidence of the effect of polyfunctionalization on cross-linking density [0047].
Conclusion
No claim is allowed.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Anderson (US 8,993,691) (polyepoxide curing agents/ crosslinkers) for thiol-functional polymers)
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 ALEXANDER M WEDDLE whose telephone number is (571)270-5346. The examiner can normally be reached 9:30-6:30.
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ALEXANDER M WEDDLE
Examiner
Art Unit 1712
/ALEXANDER M WEDDLE/Primary Examiner, Art Unit 1712
