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 . Per amendment dated 2/17/26, claims 15-30 are currently pending in the application.
It is noted that applicant made a provisional election of Group I (claim 15-25) over telephone on 9/8/25, and the response dated 2/17/26 acknowledges this election with traverse. However, because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Claims 26-28 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
It is noted that claim 24 depends on claim 15 and recites the limitation “wherein the at least one protective colloidal agent”, but claim 15 does not recite at least one protective colloidal agent as a component. In order to maintain compact prosecution, examiner is not levying a new ground on rejection under 112(b) for lack of proper antecedent basis for the limitation. However, applicant is alerted to the issue for future reference.
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.
Claims 15-24, 29 are rejected under 35 U.S.C. 103 as being unpatentable over O (US 2004/0132938 A1).
Regarding claims 15-18, 20, 22-24, 29, O teaches storage stable aqueous organic peroxide emulsions comprising an anti-freeze agent, a protective colloid, a plasticizer, and preferably an emulsifier (Ab., [0027], ref. claims 1-8). Recognizing that aqueous organic peroxide emulsions are generally considered safe products because the peroxide is dispersed, forming small droplets in the water phase, O teaches reducing the droplet growth in aqueous organic peroxide by including a specific ester plasticizer in the compositions [0003], [0008].
Disclosed organic peroxides are liquid peroxides [0020], and the disclosed genus includes peroxydicarbonates, with di-sec-butyl peroxydicarbonate being disclosed as a more preferred species of the organic peroxides [0022].
Disclosed small genus of anti-freeze agents includes methanol, ethanol, isopropanol, (ethylene) glycol, propanediol, glycerol and mixtures thereof [0024], i.e., teaches equivalence thereof, and can be used in a usual amount, typically in an amount less than the amount of water [0024].
O teaches conventional emulsifiers, such as non-ionic surfactant as a preferred species [0027].
Disclosed Example 1 is drawn to an aqueous peroxide emulsion comprising water, methanol, a peroxide (50 wt.%), and a hydrolyzed polyvinyl acetate as a protective colloid, with inhibited droplet size growth in the presence of a plasticizer.
Disclosed hydrolyzed polyvinyl acetate protective colloid meets the limitation of an emulsifier of claims 23 and 24. Additionally, noting that emulsifiers are a subset of surfactants, and given than hydrolyzed polyvinyl acetate is a non-ionic species, it also meets the limitation of claim 22.
O is silent on an emulsion comprising di-sec-butyl peroxydicarbonate dispersed as droplets in an aqueous phase, and an antifreeze agent, wherein said emulsion is free of methanol and ethanol, in one single embodiment as claimed.
At the outset, it is noted that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
Given the teaching on suitable peroxides, including di-sec-butyl peroxydicarbonate as a preferred species, and the teaching suitable anti-freeze agents, and the teaching that aqueous organic peroxide emulsions are safe products because the peroxide is dispersed as small droplets in the aqueous phase, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare an aqueous emulsion comprising dispersed di-sec-butyl peroxydicarbonate droplets in the aqueous phase, and including any of the anti-freeze agents, including those that are is free of methanol and ethanol
For instance, a skilled artisan would have found it obvious to substitute the peroxide in Examples 1, 2 or 4 with di-sec-butyl peroxydicarbonate, and to substitute methanol with any of isopropanol, (ethylene) glycol, propanediol and glycerol, based on their art recognized equivalence, absent evidence to the contrary.
It is prima facie obvious to substitute equivalents known for the same purpose, so long as the equivalency is recognized in the prior art. In re Ruff, 256 F.2d 590, 118 USPQ 340 (CCPA 1958). An express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982). See MPEP 2144.06.
With regard to claim 19, Example 4 comprises 2 parts, by wt. PVA, 1 part by wt. of DIDA (plasticizer), tert- peroxydecanoate 98%, and water/methanol (70/30 ratio), to provide for an emulsion with 50 wt.% peroxide. Absent as clear teaching on volume basis in the ratio, Examiner interprets the 70/30 ratio to mean weight ratio. The calculated wt.% of methanol in the aqueous emulsion is 13.8%, and a skilled artisan would have found it obvious to prepare similar emulsions using di-sec-butyl peroxydicarbonate as the peroxide and any of isopropanol, (ethylene) glycol, propanediol and glycerol as the anti-freeze agent in similar amounts.
Regarding claim 21, O prescribes a range of 30-70 wt.% of peroxide in the aqueous peroxide emulsions [0023].
Claims 15-24, 29, 30 are rejected under 35 U.S.C. 103 as being unpatentable over Tartarin et al. (US 2015/0218293 A1).
Tartarin teaches an aqueous emulsion comprising water, one or more organic peroxides in the form of droplets, at least one antifreeze agent, at least one emulsifying agent, and optionally and additive, wherein said emulsifying agent is a colloid agent of polyvinyl acetate, and said emulsion being prepared by dispersing the antifreeze agent, at least one emulsifier and optional one or more additive in water in order to obtain a homogeneous aqueous phase, and then adding the peroxide is added to said aqueous phase and subsequently emulsifying the mixture (Ab., [0013]-0042], [0061], ref. claims).
Disclosed genus of peroxides include di-(sec-butyl) peroxydicarbonate and di-(2-ethyl hexyl) peroxydicarbonate as preferred species [0045]. Additionally, the antifreeze agent may be methanol, ethanol, ethylene glycol, isopropanol, n-propanol, propane-1,2-diol, propane-1,3-diol, glycerol, butan-1-ol, butan-2-ol, butane-1,3-diol, butane-1,4-diol or their mixtures [0048]. That is, Tartarin teaches equivalence of the disclosed peroxydicarbonates and the antifreeze agents.
Disclosed Example 11 is drawn to an aqueous peroxide emulsion comprising di (2-ethyl hexyl)decarbonate (peroxide, 60 wt.%), water (wt. 24.8 wt.%), methanol (antifreeze, 11.2 wt.%), a hydrolyzed polyvinyl acetate protective colloid (1.2 wt.%), and ethoxylated castor oil (non-ionic surfactant, 1 wt.% (read on oxyalkylenated fatty acids/claim 30) [0075]- [0103]. Disclosed hydrolyzed polyvinyl acetate protective colloid meets the limitation of an emulsifier in claims 23 and 24.
Tartarin is silent on an emulsion comprising di-sec-butyl peroxydicarbonate droplets dispersed in an aqueous phase and an antifreeze agent, wherein said emulsion is free of methanol and ethanol, in one single embodiment as claimed.
As stated in paragraph 8 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Given the teaching in Tartarin on suitable peroxides for forming an aqueous emulsion comprising water, peroxide droplets, on suitable anti-freeze agents, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare an aqueous emulsion comprising water, hydrolyzed polyvinyl acetate protective colloid, peroxide droplets dispersed in an aqueous phase, e.g., of di-sec-butyl peroxydicarbonate, and an antifreeze agent, wherein said emulsion is free of methanol and ethanol.
For instance, a skilled artisan would have found it obvious to substitute the di-(2-ethyl hexyl) peroxydicarbonate in Example 11 with di-sec-butyl peroxydicarbonate, and substitute methanol with any of isopropanol, (ethylene) glycol, propanediol and glycerol, based on their art recognized equivalence, absent evidence to the contrary. As stated in paragraph 9 above, it is prima facie obvious to substitute equivalents known for the same purpose, so long as the equivalency is recognized in the prior art and an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. See MPEP 2144.06.
Claims 15-19, 20-22, 25, 29 and 30 are rejected under 35 U.S.C. 103 as being unpatentable over Westmijze et al. (WO 99/42078 A1).
Regarding claims 15-18, 20-22, 25, 29 and 30, Westmijze teaches aqueous peroxide emulsions, optionally containing anti-freeze agents and/or further additives, and a specific emulsifier system comprising a specific copolymer and an ethoxylated fatty alcohol (reads on emulsifier) (Ab.), said emulsion having a emulsified peroxide, that using the specific emulsifier system under high shear mixing conditions as providing for small and stable peroxide droplets size and a narrow size distribution with no phase separation during storage (page 1, lines 5-9, line 25-page 2, line 26, page 7, line 1-18).
The disclosed genus of peroxides includes di-sec-butyldicarbonate (page 3, lines 6-7). Regarding the anti-freeze agents, Westmijze teaches that the amount and type thereof depend on the nature and type of the peroxide used, and may be selected from methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and mixtures thereof in an amount of (page 6, lines 11-31).
Disclosed Examples 8 and 9 are drawn to emulsion comprising 50 wt.% bis (2-ethyl hexyl)peroxydicarbonate, 0.5% w/w Berol 08 (reads on emulsifier) (ethoxylated stearyl alcohol, degree of ethoxylation of 80, HLB-18.5, obtainable from Akzo Nobel), 2.0% w/w Darpal GE 202 (copolymer of the emulsifier system), and the balance being a mixture of anti-freeze agent, wherein the anti-freeze agent of Example 8 is ethylene glycol and that of Example 9 is propylene glycol, both emulsions being acceptable from safety and use point of view (pages 14-15).
Westmijze is silent on an aqueous emulsion comprising water, dispersed di-sec-butyldicarbonate droplets in the aqueous phase, and an anti-freeze agent, wherein said emulsion if free of methanol and ethanol, in one single embodiment as claimed.
As stated in paragraph 8 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Given the generic teaching on aqueous peroxide emulsions including small and stable peroxide droplets size and a narrow size distribution with no phase separation, and suitable peroxides and anti-freeze agents therefor, it would have been obvious to one of ordinary skill in the art, as of the effective filing system, to prepare emulsions comprising water, dispersed di-sec-butyldicarbonate droplets in the aqueous phase, an emulsifier system comprising an ethoxylated fatty alcohol, and any of the disclosed anti-freeze agents, including isopropanol, ethylene glycol, propylene glycol, glycerol or mixtures thereof.
For instance, a skilled artisan would have found it obvious to prepare an aqueous emulsion under high shear mixing as in Examples 8 and 9, by substituting 50 wt.% bis (2-ethyl hexyl)peroxydicarbonate with di-sec-butyldicarbonate, and reasonably expect the aqueous emulsions to have droplets of di-sec-butyldicarbonate dispersed in the aqueous phase, absent evidence to the contrary. As stated in paragraph 9 above, it is prima facie obvious to substitute equivalents known for the same purpose, so long as the equivalency is recognized in the prior art and an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. See MPEP 2144.06.
Regarding claim 19, Westmijze teaches that the amount and type of anti-freeze to be used depends on the nature and amount of peroxide that is being formulated as well as on the type of anti-freeze, or mixture of anti-freezes, that it is convenient to adjust the amount of anti-freeze agent(s) such that the mixture of just the anti-freeze and water that is used to form the emulsion shows a freezing point below the storage temperature necessary for handling the peroxide, that a skilled person will have no difficulties in balancing the ratio of water to anti-freeze agent such that a certain desired freezing temperature is reached, typically the amount of anti-freeze agent in the emulsion being lower than the amount of water (page 6, lines 10-31). Thus, it would have been within the level of ordinary skill in the art to provide emulsions comprising an antifreeze such as isopropanol, ethylene glycol, propylene glycol, glycerol or mixtures thereof within the scope of the claimed invention.
For instance, examiner has calculated the amount of water/antifreeze balance in Examples 8 and 9 to be at 47.5 wt.%. Thus, in Examples 8 and 9, the amount of ethylene glycol or propylene glycol may be less than the amount of water, i.e., less than 23.75 wt.%, a range that overlaps with the claimed range.
Claims 15-25, 29 and 30 are rejected under 35 U.S.C. 103 as being unpatentable over Tang et al. (US 4,515,929, of record).
Regarding claims 15-24, 29, 30, Tang teaches a peroxide dispersion (as an emulsion or suspension) comprising a peroxide, preferably a liquid in a discontinuous phase, such as such as di-sec.butyl peroxydicarbonate or di-2- ethylhexyl peroxydicarbonate, water, and a surfactant or an emulsifying agent (Ab., col. 5, lines 18-23, col. 6, lines 42-53, col. 6-7, bridging paragraph, col. 8, line 60-col. 11, line 29, ref. claims 1, 9, 12).
Disclosed peroxide dispersions may include materials capable of lowering the freezing point of the dispersion (i.e., antifreeze materials), e.g., alkanols having 1-4 carbon atoms or alkane diols having 2-4 carbon atoms, at about 2 to about 20% by weight of the dispersion (col. 11, 30-52).
As surfactants, Tang teaches ethoxylated C₁₂-C₁₈ alcohols (encompass with oxyalkylenated fatty alcohols) and ethoxylated natural fats and oils, such as ethoxylated are lauryl, oleyl, cetyl, stearyl, tridecyl, myristyl, trimethylnonyl, C12 -C15 primary linear and C.sub.11 -C.sub.15 secondary alcohols (i.e. ethoxylated fatty alcohols), glycerol esters are either mono- or diglycerides of fatty acids, such as C12 -C18 fatty acids, mono-, di- or triesters of sorbitan and fatty acids, ethoxylated sorbitan fatty acid esters having 4-20 oxyethylene units per moles of ester etc. (col. line 6-col. 10, line 40). Thus, Tang’s emulsifiers/nonionic surfactants overlap in scope with the emulsifiers/nonionic surfactants of claims 22 and 30.
Disclosed Example 1 is drawn to an aqueous emulsion comprising water, di-2-ethylhexyl peroxydicarbonate (30 wt.%), polyvinyl alcohol (reads on emulsifier/protective colloid), ethoxylated nonyl phenol (reads on nonionic surfactant), and water.
Tang is silent on an emulsion comprising di-sec-butyl peroxydicarbonate droplets dispersed in an aqueous phase and an antifreeze agent, wherein said emulsion is free of methanol and ethanol, in one single embodiment as claimed.
As stated in paragraph 7 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Given the teaching on aqueous emulsion compositions comprising a peroxide, preferably a liquid in a discontinuous phase, suitable peroxides and materials for lowering the freezing point, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare an aqueous emulsion comprising any peroxide, e.g., di-sec.butyl-peroxydicarbonate, water, an emulsifying agent, and an alkanol having 3 or 4 carbon atoms or an alkane diol having 2-4 carbon atoms, and reasonably expect the peroxide liquid to be present as droplets in the aqueous phase, absent evidence to the contrary.
For instance, it would have been obvious for a skilled artisan to prepare an aqueous emulsion as in Example 1, by substituting di-2-ethylhexyl peroxydicarbonate with di-sec-butyl-diperoxycarbonate, based on their art recognized equivalence, an emulsifier, and an alkanol having 3 or 4 carbon atoms or an alkane diol having 2-4 carbon atoms in prescribed amount by the disclosed method, and reasonably expect the di-sec-butyl-diperoxycarbonate to be dispersed as droplets in the aqueous phase.
Alternatively, a skilled artisan would have found it obvious to prepare an aqueous emulsion comprising water, di-sec-butyl-diperoxycarbonate, an emulsifier such as an ethoxylated C₁₂-C₁₈ alcohol or an ethoxylated natural fat or oil, that falls within the scope of claim 30, and an alkanol having 3 or 4 carbon atoms or an alkane diol having 2-4 carbon atoms in prescribed amount, by the method of Example 1, and reasonably expect the peroxide to be dispersed as droplets in the aqueous phase, absent evidence to the contrary.
Regarding claim 25, Tang teaches that the surfactant can be nonionic, cationic or amphoteric, typically nonionic, that combination of two or more surfactants or colloids are commonly used, and that the selection depends on the peroxide and the polymerization in which the emulsion will be used (col. 8, lines 26-42), i.e., the peroxide composition may be free of polyvinyl alcohol and hydrolyzed polyvinyl acetate.
Response to Arguments
In view of the amendment dated 2/17/26, the rejections of record are withdrawn and new grounds of rejections are presented herein above. Applicant’s arguments with regard to Tang et al. (of record and relied herein above) have been duly considered and arguments pertinent to rejections above are addressed.
Referring to the analysis in Tang on instability of aqueous emulsions at storage temperatures of 5°C to +20°C and the addition of diphenyl peroxydicarbonate (DPP) as a stabilizer to slow homolytic decomposition, applicant argues that Tang expressly embraces using methanol, ethanol, and other C1-C4 alcohols-along with certain glycols-as antifreezes at 2-20 wt% for maintaining pumpability and avoiding freeze-related thickening, but nothing in Tang suggests that methanol or ethanol could present a peroxide-specific incompatibility and that the present invention identifies such incompatibility.
Applicant further asserts that the data of record confirms that excluding methanol and ethanol yields unexpected, durable stability, that emulsions containing ethanol (and, by the same mechanism, methanol) rapidly demix and may generate pressure within weeks-or in some cases within hours-because the di-sec-butyl-diperoxycarbonate (DSBP) decomposes, and that in contrast, MeOH/EtOH-free emulsions using propane-1,2-diol remain homogeneous for at least six months, preserving both average and maximum droplet sizes and maintaining top/bottom peroxide concentrations within the claimed homogeneity threshold. Applicant concludes that these outcomes are not incremental improvements, they contradict industry expectations based on Tang's antifreeze guidance and represent an entirely different stability profile.
In response, it is noted that claim 1 is drawn to a peroxide composition, as an emulsion, comprising di-sec-butyl-diperoxycarbonate droplets dispersed in the aqueous phase, said composition comprising at least one emulsifier, at least one antifreeze, and water, and said emulsion being free of methanol and ethanol. For reasons presented in the earlier office action and herein above, Tang teaches the positively recited components of claim 1 and may be free of methanol and ethanol because of the alternative anti-freeze agents taught therein. Tang further teaches di-sec-butyl-diperoxycarbonate as a suitable peroxide, di-sec-butyl-diperoxycarbonate as a preferred species of peroxydicarbonate esters (col. 5, lines 10-23). Additionally, the transitional phrase “comprising” in claim 1 does not necessarily exclude Tang’s stabilizer.
As for the assertion that the data of record confirms that excluding methanol and ethanol yields unexpected, durable stability, the data on record (Tables 1-3) shows that Inv. emulsions of Ex. 7-9 demonstrate superior stability. However, the data on superior stability is also limited to specific compositions of Ex. 7-9 comprising water, di-sec-butyl-diperoxycarbonate (Luperox 225), PVA or Surfaline LG15 (emulsifier) and propane 1,2-diol (antifreeze) in specific amounts. It is not clear why these specific compositions of Ex. 7-9 would be considered reasonably representative of claim 1 that is open ended to the antifreeze and emulsifier or amounts thereof.
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 Satya Sastri at (571) 272 1112. The examiner can be reached Monday-Friday, 9AM-5.30PM (EST). If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Mr. Robert Jones can be reached at (571)-270-7733. The fax phone number for the organization where this application or proceeding is assigned is (571) 273 8300.
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/Satya B Sastri/
Primary Examiner, Art Unit 1762
Prosecution Insights