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 .
Claim Status
Claims 1-15 are pending and currently amended.
Claim Rejections - 35 USC § 112
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.
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.
Claims 2, 3, and 15 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as failing to set forth 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.
Regarding Claim 2:
Claim 1 recites “by an interfacial polymerization reaction…”, while Claim 2, depending on Claim 1, recites “the polymerization step”. While likely understood in context, strict antecedent basis practice here supports an indefiniteness rejection. It is recommended an amendment to use “interfacial polymerization reaction” consistently in the Claim 2.
Regarding Claim 3:
Claim 3 recites “advantageously consisting of a derivative…”. The word “advantageously” is aspirational/optional language carried over from the instant Application’s specification (page 2, line 23), and left in the claim section. The word “advantageously” renders unclear whether the recited “5-(4H)oxazolone” derivative is a required claim element or merely a preferred, non-limiting characterization of Formula (I). MPEP 2173.05(b)(III) clearly defines the terms of degree/approximation without clear standard for measuring scope. As written “advantageously”, one cannot tell if a first reactive molecule falling within Formula (I) is inside or outside of the claim.
It is recommended to amend Claim 3 by deleting “advantageously”, instead using “consisting of…”, for example.
Regarding Claim 15:
Claim 15 recites “A core-membrane capsules” which has grammatical mismatch (“a… capsules”) renders unclear whether Claim 15 is directed to a single capsule or a plurality, and creates ambiguity as to the metes and bounds of the claimed subject matter. It is recommended an amendment to correct this.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 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.
2. Claims 1-6, 10-11 and 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2007/042438 A1 (De Corte et al.), hereafter referred as De Corte, in view of US 4,485,236 (Rasmussen et al.), hereafter referred as Rasmussen.
Regarding Claim 1:
De Corte discloses a method for manufacture of core-membrane capsules by interfacial polymerization comprising:
supplying two immiscible solutions respectively containing reactive molecules capable of reacting together by an interfacial polymerization/polycondensation reaction to form a membrane/shell. “The interfacial polymerization method depends on the reaction of two interfacial polymerizable monomers at the interface of an oil-in-water emulsion. Generally an oil soluble first monomer is dissolved in the disperse phase and a second water-soluble monomer is added to the aqueous phase.” (De Corte, p11, lines 15-18). De Corte further discloses that crosslinked polymer of resulting shell is selected from a list expressly including “polyamides” (De Corte, p11, line 33). And one of the immiscible solutions, intended for forming the core, contains at least one active ingredient – “luminescent pigment” (De Corte, p12, line 4).
One of the immiscible solutions – oil phase, intended to form the core, contains at least one active ingredient (lumincent pigment), which becomes the capsule core.
an interfacial polymerization step in which the solution containing the active ingredient (luminescent pigment) forms dispersed droplets (the core), and the other solution forms a continuous phase (aqueous phase), and the two monomer solutions react at the droplet interface to form the encapsulating shell. (De Corte, p34 line 23 – p35 line 6, Example 1,). “The monomers react by polycondensation reaction at the interface between the dispersed oily droplets and surrounding aqueous medium and forming a polymeric membrane around the oil droplets.” (De Corte, p11, lines 18-20).
De Corte’s exemplified at the end shell-forming monomer chemistries are isocyanate-based (polyurea/polyurethane) “polymeric membranes formed are polyurea and polyurethane's as described in US3429827 and US 4428978.” (De Corte, p11, lines 20+21) or aminoplast (melamine-formaldehyde) (De Corte, p11, lines 23-25), or polyethylene glycol-type. It is also noted that De Corte separately discloses azlactones as one recognized ingredient itself (De Corte, p8, lines 1-5), the “few important representative examples” provided are azlactones depicting a 2-aryl-oxazole-5(4H)-one.
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and “A microencapsulated luminescent pigment according to claim 1 … is selected from the group consisting of … azlactones…” (De Corte, Claim 5, p39, line 22), as well as
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(De Corte, p40, Claim 7, lines 1-4).
The azlactone-based structure functions in De Corte, being not identical to or similar to the ones claimed in the instant Application for shell-forming chemistry, is not disclosed as reacting with an external polyamine to form the capsule’s polyamide shell. De Corte’s disclosure of azlactone-ring-containing structure as a recognized, art-conventional chemical class within the same microencapsulation/pigment field. It is nonetheless probative that a person of ordinary skill reviewing De Corte and noting that De Corte states only few examples are provided, would not regard azlactone chemistry generally as unrelated or foreign to the technology at issue, and would accordingly have looked to the separate, well-developed body of art directed to azlactone ring-opening reactivity for al alternative shell-forming chemistry. That body of art, however, is explicitly exemplified by Rasmussen.
Rasmussen, in the same field of endeavor of azlactone-functional reaction chemistry, discloses azlactone-functional bis- and tris-azlactone monomers (Formula I)
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prepared by reacting alkenyl azlactones with nucleophilic compounds “by a Michael Reaction” (Rasmussen, col. 2 line 63 – col. 3 line 27), and further discloses Formula IV that these azlactone compounds react with primary-amine-functional chain crosslinking/curing agents to form “polyamide resins” (Rasmussen, Abstract) and “When the nucleophilic compound is amine-functional, particularly primary amine-functional, the reaction to produce the polyamides of Formula IV proceeds rapidly” (Rasmussen, col. 8, lines 55-57).
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Rasmussen’s Example 10 discloses formation of an azlactone-functional/bis-azlactone product by reacting “2-ethenyl-4,4-dimethyl-2-oxazolin-5-one” with “poly(oxypropylene diamine)” (Rasmussen, col. 11, lines 1-20).
And Rasmussen further discloses Formula (IV) reacts with primary-amine functional “Nucleophilic group-functional chain-extending or crosslinking agents” (Rasmussen, col. 7, lines 45-46), and expressly including “ethylenediamine, …, 1,6-hexanediamine, …, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine; …, and polyethylene imines” (Rasmussen, col. 7, line 59 – col. 8 line 16), to form polyamide resin system (Rasmussen, Abstract). Rasmussen further discloses that “The electrophilicity of the azlactone group is such that these resins display reactivity which is intermediate between that of epoxies and that of isocyanates. That is, the azlactones are more reactive towards nucleophiles than are epoxy resins, but are much more controllable in their reactivity than are isocyanates and are not so susceptible to contamination by water.” (Rasmussen, col.7, lines 37).
This is a simple substitution of one known reactive wall-forming component (one azlactone) for another known, art-recognized reactive component (bis-azlactone) to obtain a predictable result of an interfacially polymerized polymer wall. MPEP 2143(I)(B) and (G) “Simple Substitution of One Known Element for Another To Obtain Predictable Results” “Some Teaching, Suggestion, or Motivation in the Prior Art That Would Have Led One of Ordinary Skill To Modify the Prior Art Reference or To Combine Prior Art Reference Teachings To Arrive at the Claimed Invention”.
It would have been obvious to a PHOSITA at the effective filing date of the invention to substitute Rasmussen’s azlactone-functional chemicals (i.e., the first reactive reactant having at least two azlactone groups) and polyamine such as diethyleneamine, or other amines stated above, (i.e., the second reactive reactant, having at least two amine groups) for the isocyanate/amine reactive pair or aminoplast reactive pair or azlactone-ring-containing structure used in De Corte’s interfacial-polymerization core-membrane capsule process because both pairs are art-recognized reactive pairs chemistries known to form a crosslinked polyamide-type membrane, and Rasmussen himself expressly discloses that azlactone/polyamine chemistry is “much more controllable in their reactivity than are isocyanates and are not so susceptible to contamination by water.” (Rasmussen, col. 7, lines 35-36). This is a direct motivation from the prior art itself to prefer azlactone chemistry over the isocyanate chemistry, particularly given that isocyanate toxicity concerns are the very problem the instant Application identifies as its reason for seeking an alternative. This is a simple substitution of one known element (an isocyanate/amine reactive or an aminoplast reactive pair) for another known element (an azlactone/amine reactive pair), motivated by an explicit teaching in the prior art, to obtain a predictable result (a crosslinked polyamide membrane around a core containing an active ingredient).
Regarding Claim 2:
De Corte’s preferred embodiment expressly assigns the first reactive reactant being oil-soluble phase as the dispersed phase, as stated above, and the second phase being water-soluble solution to be the continuous phase, also as stated above. This renders Claim 2 obvious for the reasons set forth in the above analysis for the Claim 1.
Regarding Claim 3:
De Corte teaches the rejection of claim 1 above. De Corte doesn’t but Rasmussen discloses in claim 1 (Rasmussen, claim 1, col. 13 line 31- col. 14 line 8):
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“R3 and R4 are independently an alkyl or cycloalkyl group having up to 12 carbon atoms, an aryl or aralkyl group”, which corresponds to the instant Application’s Formula (I)’s “R1 and R2 independently represent a (C1-C10)alkyl group, a (C3-C6)cycloalkyl group, an aryl group, an aryl(C1-C10)alkyl group, or a heterocyclic group.”. Rasmussen further discloses the azlactone ring is a derivative, “particularly with regard to the 5-membered rings, the 2-alkenyl-2-oxazolin-5-ones.” (Rasmussen, col. 4, lines 9-10), which corresponds to the instant Application’s Claim 3 of “a derivative of a 5-(4H)oxazolone”. These substantially overlapping substituent definitions render the claimed Formula (I) obvious as a routine selection among the art-recognized equivalent derivatives for the same base azlactone ring structure.
MPEP 2143(E) “"Obvious To Try" – Choosing From a Finite Number of Identified, Predictable Solutions, With a Reasonable Expectation of Success”. “The rationale to support a conclusion that the claim would have been obvious is that "a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103."KSR, 550 U.S. at 421”.
A PHOSITA would have been motivated to select any one of these derivatives to form the target polymer – polyamide. In fact, Rasmussen teaches both the motivation, i.e., more rapidly (Rasmussen, col. 6, line 39) and more controllable curing process (Rasmussen, col. 7, line 35), and the expectation of success shown by his example (Rasmussen, Example 10, col. 11, lines 1-7) for such a selection.
Therefore it would have been obvious for one of ordinary skill in the art at the effective date of the invention to select any derivative of azlactones taught by Rasmussen with the polyamines of De Corte and to react with polyamine to form the target polymer as the capsule wall as the intended invention.
Regarding Claim 4:
De Corte teaches the rejection of claim 1 above. De Corte doesn’t but Rasmussen discloses azlactone-functional chemicals and its derivatives have at least two azlactone groups, for example, bis-azlactone per Formula (I)
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“R is a mono or polyvalent organic group that has a valence of ‘n’ and is the residue of a nucleophilic group-substituted compound” (Rasmussen, col. 13, lines 30-65), prepared my Michael Addition) (Rasmussen, col. 10, lines 55-64, Table 1).
Selecting Rasmussen’s bis-azlactone as the first reactive reactant in the combined De Corte/Rasmussen method is an obvious choice of experimentation and optimization between the known and art-recognized alternatives of azlactone-functional reactive reactants, each performing its known function with an amine chemical/derivative to form polyamide polymer.
Regarding Claims 5-6:
De Corte teaches the rejection of claim 1 above. De Corte doesn’t but Rasmussen discloses “After 24 hours, IR analysis indicated complete conversion to the bis(azlactone).” (Rasmussen, col. 11, lines 17-18) and “The resultant tris(azlactone) was identified by spectroscopic analysis.” (Rasmussen, col 10, lines 42-43), which corresponds to the instant Application’s Claim 4 “at least two azlactone groups” and Claim 5 “bis-azlactone”.
Rasmussen’s reference Humbert’s teaching “Humbert, et al., U.S. Pat. No. 4,092,298, teach the use of bis(azlactones), wherein the linking group is a hydrocarbon or halo-substituted hydrocarbon group, as novel crosslinking agents for hydroxy-containing polymeric powder coating compositions.” (Rasmussen, col. 1, lines 37-42). And Rasmussen teaches that
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“R is an organic group that has a valence of ‘n’ and is the residue of a nucleophilic group-substituted compound, (HX)nR, in which X is defined above, the residue having a molecular weight up to 20,000, preferably selected from mono- and polyvalent hydrocarbyl (i.e., aliphatic and aryl compounds having 2 to 20 carbon atoms and optionally one to four catenary heteroatoms of oxygen, nitrogen or sulfur” (Rasmussen, Claim 1, col.13 line 64 – col. 14 line 4 & Claim 7 col. 14 line 38-col. 16 line 8), which directly corresponds to the instant Application’s Claim 5 “from 1 to 30 carbon atoms” and the instant Application’s Claim 6 Formula (II) which contains “one or more oxygen or sulfur atoms” is also taught by Rasmussen’s above disclosure.
Rasmussen discloses (Rasmussen, col. 6 line 37 – col. 7. Line 26) bis-azlactone compounds having two terminal azlactone rings connected by a bridging chain that includes heteroatoms contributed by the Michael donor compound used to make them – e.g., “1,2-bis[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)ethylthio]ethane, 1,5-bis[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)ethylthio]3-oxapentane, 1,10-bis[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)ethylthio]4,7-dioxadecane-3, 8-dione, 1,1,1-tris[[2-[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)ethylthio]ethylcarbony loxymethyl]]propane, 1,5-bis[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)-2-methylethylthio]-3-oxapentane, 1,5-bis[2-(4-methyl-4-nonyl-2-oxazolin-5-one-2-yl)-ethylthio]-3-oxapentane, 1,5-bis[2-(4,4-dimethyl-2-oxazolin-5-one-2-yl)ethylthio]-3-thiapentane.” Each of these compounds has an aliphatic hydrocarbon group connected/bridged by one or more sulfur (or oxygen) atoms. Rasmussen thus discloses the bis-azlactone first reactive molecule of Claims 5-6, i.e., anticipates this particular structural feature, such that its incorporation into the combined De Corte/Rasmussen method of Claim 1 is obvious for the reasons given above.
Therefore, Del Corte in view of Rasmussen’s disclosures of these azlactone-functional compounds are not merely suitable alternatives but fully encompass the instant Application claim’s ranges. The Application’s claim of azlactone chemicals lies entirely inside, or substantially overlaps, a range already disclosed in the prior art. MPEP 2144.09 (I) “REJECTION BASED ON CLOSE STRUCTURAL SIMILARITY IS FOUNDED ON THE EXPECTATION THAT COMPOUNDS SIMILAR IN STRUCTURE WILL HAVE SIMILAR PROPERTIES”
Thus the burden is shifted to the instant Applicant to show his range of azlactone chemicals produces a new and unexpected result. Both Rasmussen and the instant Applicant use these chemicals for the same purpose – forming polyamide chemistry – no unexpected results have been disclosed, and a PHOSITA would have had a reasonable expectation of success that any azlactones within the range would work as Rasmussen describes.
Regarding Claim 10:
De Corte itself discloses interfacial polymerization forming the dispersed/continuous phase mixture by an emulsification operation (oil-in-water emulsion). (De Corte, p11, lines 15-16)
Dripping and (shear) emulsification are both well-known, art-recognized techniques for the purpose of generating discrete droplets of a dispersed phase for interfacial-polymerization process of microencapsulation, as evidenced by De Corte’s disclosure forming the dispersed/continuous phases by emulsification operation (oil-in-water emulsion) (De Corte, p10, line 27), as well as by the instant Applications own acknowledgment that dripping is simply an alternative droplet-generation “operation” (page 4, lines 12-15). Substituting a droplet-generation technique known to be interchangeable for the same purpose and in the same interfacial-polymerization process, is a straightforward application of a known technique to improve and optimize a similar process in the same way.
A PHOSITA would have had a reasonable expectation of success because the droplet formation, using dripping or shear emulsification, produces the same physical results regardless of which technique is used.
Regarding Claim 11:
Claim 11, depending from Claim 1, which is rendered obvious by De Corte in view of Rasmussen as set forth above, further requires that the second reactive molecule (the amine-containing molecule) is selected from “molecules of synthetic nature” or “of natural origin”.
Rasmussen expressly discloses suitable nucleophilic amine “nucleophilic group-substituted chain-extending or crosslinking agent” (Rasmussen, col. 3, lines 41-42) for reaction with the azlactone-functional reactive reactants as stated in the section “2. Claim 1” “ethylenediamine, 1,4-butanediamine, benzenediamines, 1,4-cyclohexanediamine, 1,6-hexanediamine (i.e., HMDA), N,N'-bis(3-aminopropyl)piperazine, diethylenetriamine (i.e., DETA), triethylenetetramine, and tetraethylenepentamine; …; polyethylene imines (i.e., PEI)” (Rasmussen, col. 7, line 59 – col. 8 line 16). These are synthetic amines as claimed by the instant Application Claim 11.
It would have been obvious to a PHOSITA at the time of effective filing time of the invention to select a synthetic polyamine disclosed by Rasmussen as the second reactive molecule in the combination of De Corte and Rasmussen. A PHOSITA would have recognized that selecting between synthetic polyamines and natural-origin polyamines represents choosing from routine, well-known classes of amine crosslinkers with a reasonable expectation of success of forming the intended polyamide capsule membrane.
Regarding Claim 13:
Claim 13 depends from Claim 1, which is rendered obvious by De Corte in view of Rasmussen as set forth above, and further recites “… contains a surfactant”.
Surfactant use to stabilize any dispersed-droplets/continuous-phase emulsions is taught in De Corte’s own oil-in-water emulsion process. “To prevent the encapsulated particles of the invention coagulating and subsequently phase separating in the environment in which they are to be used, an entropic stabilizing polymer, such as carboxymethyl cellulose, sodium alginates or starch, can be mixed with the LCST polymeric component prior to encapsulation.” (De Corte, p11, lines 9-13) where “sodium alginates or starch” plays a role of surfactant.
Regarding Claim 14:
Claim 14 depends from Claim 1, which is rendered obvious by De Corte in view of Rasmussen as set forth above, and further recites “… free of isocyanates”.
As stated in the section “Regarding Claim 1”, Rasmussen discloses azlactone-functional bis- and tris-azlactone monomers (Formula I) prepared by reacting alkenyl azlactones with nucleophilic compounds “by a Michael Reaction” (Rasmussen, col. 2 line 63 – col. 3 line 27), and further discloses Formula IV that these azlactone compounds react with primary-amine-functional chain crosslinking/curing agents to form polyamide resins (Rasmussen, col. 3, lines 28), the resulting immiscible solutions are therefore without the use of isocyanate chemistry.
Because the combined teachings of De Corte and Rasmussen render obvious and azlactone/amine reactive pair as a full substitute for an isocyanate-based reactive pair as stated in the section “2. Claim 1”, a substitution independently and expressly motivated by Rasmussen’s own teaching that azlactone chemistry is preferable to isocyanate chemistry, the resulting immiscible solutions of the combined method are necessarily “free of isocyanate”.
It would have been obvious to a person of ordinary skill (PHOSITA) before the effective filing date of the invention to substitute a bis-azlactone reactive chemical molecule of Rasmussen for the polyisocyanate of De Corte’s oil phase, and keeping De Corte’s amine-bearing aqueous phase and its dispersed-droplet/interfacial-reaction combination, automatically yielding to a “free of isocyanate” solution reaction operation.
Regarding Claim 15:
Claim 15 depends from Claim 1, which is rendered obvious as set forth above, further recites “… including a polyamide membrane”.
Claim 15 is a product-by-process claim. A product-by-process claim is rendered obviously as a necessary structural consequence of the obvious method of Claim 1, which forms a polyamide network through azlactone-amine ring-opening Michael Addition. Note that determination of patentability is based on the product itself, and the patentability of a product does not depend on its method of production, in re Thorpe, 777 F.2d 695, 698 (Fed. Cir. 1985), and in re Pilkington, 411 F.2d 1345 (CCPA 1969).
It would have been obvious for one of ordinary skill at the effective date of filing to have combined the teachings of De Corte in view of Rasmussen, independent of the specific process or method, leading to core-membrane capsule comprising a polymer polyamide. As analyzed by the above in the section of “Regarding Claim 1”, a capsule containing a polyamide membrane formed at a droplet interface is accordingly predictable result and structure of the obvious combination already established for Claim 1. Therefore, Claim 15 is rejected as a product-by-process claim.
3. Claims 7-9 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2007/042438 A1 (De Corte et al.), hereafter referred as De Corte, in view of US 4,485,236 (Rasmussen et al.), hereafter referred as Rasmussen, and further in view of US 5,408,002 (Coleman et al.), hereafter referred as Coleman.
Regarding Claim 7:
Claim 7 depends from Claim 4 which ultimately depends from Claim 1 which is rendered obvious by De Corte in view of Rasmussen as set forth above, and further recites here that the “the polyazlactone polymers meet the following criteria: - a molecular weight ranging from 1,000 g/mol to 1,000,000 g/mol, and/or - a number of azlactone groups ranging from 20 to 70.”
De Corte in view of Rasmussen fails to teach the synthesis of azlactone functional homopolymers or polyazlactones such as PVDM claimed in the instant Application which can react with amine derivatives. Polymers of the polyazlactone type, for example homopolymer poly(2-vinyl-4,4-dimethylazlactone) (PVDM), are advantageously preferred by the instant Application. Coleman discloses exactly this class of reactant – a “method of making azlactone-functional homopolymers by bulk homopolymerization” (Coleman, Abstract), and reports several such homopolymers of “Poly(2-vinyl-4,4-dimethylazlactone) (“PVDM”)” with Mn of 34,600 g/mol (Coleman, col. 21, lines 8-9, & Table 10), 15,700 g/mol (Coleman, col. 22 , col. 21, line 55 and Table 12), and 4,000 g/mol (Coleman, col. 23 line 41, and Table 18). Each of these disclosed data falls squarely within the claimed range of molecular weight of 1,000 to 1,000,000 g/mol, therefore Coleman’s teaching meets the claimed range for the “molecular weight” of Claim 7. Because Claim 7 uses “and/or”, satisfaction of either the “molecular weight” or “number of azlactone groups” is sufficient, and Coleman’s disclosure of a molecular weight within the claimed range is therefore by itself sufficient.
The instant Application’s Claim 7 of “molecular weight” lies inside a range already disclosed in the prior art. This gives a prima facie case of obviousness. MPEP 2144.05(I) “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). A PHOSITA combining De Corte’s core-membrane process with Rasmussen’s azlactone reaction chemistry, and further substituting Coleman’s polylactone homopolymer for Rasmussen’s small-molecule bis-azlactone (as claimed in Claim 4), would have done with a reasonable expectation of success, because Coleman expressly teaches that molecular weight of PVDM homopolymer is a controllable, result-effective variable achieved simply by adjusting bulk-homopolymerization conditions (e.g., initiator concentration, reaction conditions like temperature, etc.) (Coleman, col. 7 line 34 – col. 8 line 54). Optimizing this known and result-effective variable (Mn) to arrive at the claimed range would have been routine experimentation and optimization. MPEP 2144.05(II).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of effective filing date of the invention to select a polylactone reactant meeting the molecular weight or azlactone numbers criteria of Claim 7 for the reasons stated above.
Regarding Claim 8:
Claim 8 depends from Claim 7 in turn from Claim 4 and ultimately from Claim 1, and further limits the first reactive molecule to general formula (III), and reciting: “R3 represents an aliphatic, linear or branched, hydrocarbon group comprising from 1 to 30 carbon atoms which can be interrupted by one or more oxygen or sulfur atoms, R1 and R2 independently represent a (C1-C10)alkyl group, a (C3- C6)cycloalkyl group, an aryl group, an aryl(C1-C10)alkyl group, or a heterocyclic group, and n represents an integer from 20 to 70.”
Coleman discloses the identical oxazolinone-moiety group attached to a polymer backbone “"Azlactone" means an oxazolinone moiety of Formula I” (Coleman, col. 2 line 67 – col. 3 line 20):
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in which “R1 and R2 independently can be an alkyl group having 1 to 14 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 5 to 12 ring atoms, an arenyl group having 6 to 26 carbon atoms and 0 to 3 S, N, and nonperoxidic O heteroatoms, or R1 and R2 taken together with the carbon to which they are joined can form a carbocyclic ring… n is an integer 0 or 1” (Coleman, Claim 2, col. 37, lines 33-54, & Claim 6 col. 37 line 66 – col. 38 line 38). Coleman’s disclosed alkyl range (C1-C14) fully subsumes the claimed C1-10 range, and Coleman’s disclosed cycloalkyl range (C3-C14) fully subsumes the claimed C3-C6 range. MPEP 2144.09(I) "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Coleman also discloses that “azlactone-functionality is provided to an azlactone-functional composition by 2-alkenyl azlactone monomers.” (Coleman, col. 6, lines 51-54), and expressly identifies “The preferred 2-alkenyl azlactones include 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one (referred to herein as VDM) and 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one (referred to herein as IDM).” (Coleman, col. 7, lines 6-9). Polymerization of the monomers IDM and VDM, respectively:
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produces exactly the backbone recited in the instant Application Claim 8’s Formula (III), in which R3 is methyl – a (C1) aliphatic hydrocarbon group squarely meeting the claimed “1 to 30 carbon atoms” limitation. And Coleman’s teaching of “Bulk Homopolymerization of Azlactone-Containing Monomers” (Coleman, cols. 7-8) also applies to VDM “2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one” which is also one of preferred azlactones.
While Coleman does report Mn of the homopolymers rather than degree of polymerization, the two parameters are directly related through the repeat-unit of the azlactone monomer (approximately 139 – 153 g/mol for VDM/IDM-type unit). Coleman’s lowest disclosed molecular weight Mn=4,000 g/mol (Coleman, Table 18, col. 23, lines 45-53), corresponds to a degree of polymerization of about 26-29 (4000/153≈26 or 400/139≈29), which falls within the claimed range of 20-70. Coleman’s higher Mn examples like 15,700 g/mol, or 34,600 g/mol (Coleman, Table 12, and Table 16), correspond to “n” values above 70. However, selecting a molecular weight or degree of polymerization within the claimed subrange would have been routine experimentation and optimization of a result-effective variable that Coleman itself identifies as a tunable via its disclosure of “Bulk Homopolymerization of Azlactone-Containing Monomers” (Coleman, col. 7 line 34 – col.8 line 54). MPEP 2144.05(II).
Therefore, it would have been obvious to a PHOSITA to use Coleman’s polylactones homopolymer of Formula (III)-type structure, for example a VDM-derived PVDM, as the first reactive molecule in the De Corte/Rasmussen combination, with a reasonable expectation of success, for the reasons of adjusting and controlling viscosity, wall/film thickness, and crosslinking density, etc., already discussed above.
Regarding Claim 9:
Claim 9 depends from Claim 8 in turn from Claim 7 in turn from Claim 4 and ultimately from Claim 1, and further limits the first reactive molecule to a general Formula (IV), a specific homopolymer in which: R1 = R2 = methyl. The instant Application’s specification states “Such a molecule is also called poly(2-vinyl-4,4-dimethylazlactone) (PVDM).” (spec, page 10, line 21). Coleman’s disclosure is directed to this identical compound. Coleman repeatedly and expressly identifies its homopolymer product as “Poly(2-vinyl-4,4-dimethylazlactone), PVDM” (Coleman, col. 16, lines 23-24), and all examples and its monomer VDM “monomeric 2-ethenyl-4,4-dimethyl-2-oxazoline-5-one, VDM” (Coleman, col. 18, lines 43-44, Examples 9-12). Because the instant Application Claim 9’s Formula (IV) and Coleman’s PVDM are the same compound under the same name, this limitation is rendered obvious because it is taught expressly by Coleman. This gives a strong motivation and reasonable expectation of success for the substitution already established with respect to Claim 8, in turn Claim 7, in turn Claim 4, and finally Claim 1.
Therefore, it would have been obvious for a PHOSITA at the time of effective filing date of the invention to use Coleman’s polylactones homopolymer of Formula (III)-type structure, for example a VDM-derived PVDM as the first reactive reactant in the De Corte/Rasmussen’s combination. Selecting the specific species expressly disclosed and identified as preferred in the prior art such as PVDM provides a prima facie case of obviousness. Furthermore, the structural identity taught by Coleman provides strong motivation and reasonable expectation of success for the substitution, as already discussed with respect to Claim 8, ultimately Claim 1. MPEP 2144.09(I)
Regarding Claim 12:
Claim 12, depending from Claim 11 and ultimately from Claim 1, which is rendered obvious by De Corte in view of Rasmussen as set forth above, further speculates the reactive molecules are selected from specific pairs comprising a first reactive molecule (Formula (II) or Formula (IV)) and a second reactive molecule selected from one of DETA, TREN, HMDA, PEI, chitosan.
The specific pairs recited in the Claim 12 are each obvious combination of a known azlactone functional reactive reactant (Formula (II) bis-azlactone as disclosed by Rasmussen stated above) and Formula (IV) PVDM as stated above by Coleman) with a known polyamine as the second reactive reactant (DETA, HMDA, PEI, etc., as set forth above for Claim 11’s analysis), and natural polyamines like chitosan are conventional, art-recognized primary amine crosslinking agents routinely used in interfacial polymerization (polycondensation), amine-azlactone nucleophilic ring-opening reactions, and commercially available primary-amine crosslinking/curing agents.
It would have been obvious to a PHOSITA to select any of the specific claimed amine crosslinkers (HMDA, DETA, TREN, PEI, or chitosan) to react with the azlactone-functional first reactive molecule in the process of De Corte/Rasmussen combination. The substitution or selection of these specific primary amine crosslinkers relies on an identical ring-opening reaction mechanism yielding predictable polyamide crosslinked structures. Therefore, achieving the claimed pairs represents choosing from a finite number of identified, predictable solutions with a reasonable expectation of success. MPEP 2143 (E); KSR Intl’l Co. v. Teleflex Inc., 550 U. S. 398, 421 (2007).
Other Pertinent Prior Art References
The prior art made of record and not relied upon is considered pertinent to applicant’s disclosure:
“Fabrication of covalently crosslinked and amine-reactive microcapsules by reactive layer-by-layer assembly of azlactone-containing polymer multilayers on sacrificial microparticle templates” by Saurer et al. (Journal of Materials Chemistry, vol. 21, pp 1736-1745, 2011), teaches that any primary-amine-containing molecule for example “branched poly(ethylene imine)” (BPEI) reacts directly with an azlactone-functional polymer PVDMA through residual azlactone functionality.
TW 201544551 A “Thermochromic Color-memory Composition And Thermochromic Color-memory Microcapsule Pigment Encapsulating The Same” (Ono et al.), 2015-02-06, discloses a composition comprising electron-donating and coloring organic compound (azlactone compound) and an electron-accepting compound (an ester compound) with microencapsulation known as an interfacial polymerization method using aromatic polyisocyanate.
JP 2008509237 A “Functionalized Particles” (Torsten Kulke et al.), 2005-07-25, discloses functionalized particles formed by using polyisocyanate derivatives and polyamine leading to a formation of shell and core consisting of a polyurethane or polyurea matrix obtained by interfacial addition polymerization.
CN 108325389 A “An Azlactone Based Polyamide Film And Preparation Method Thereof” (Niu et al.), 2018-01-29, discloses an azlactone-based polyamide film (electrically reverse osmosis membrane) using primary amine and azlactone (oil-phase) by interface polymerization reaction.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant’s disclosure:
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/G.S./
Examiner, Art Unit 1765
/HEIDI R KELLEY/Supervisory Patent Examiner, Art Unit 1765
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