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 .
THIS ACTION IS MADE FINAL. 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.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-5, 9 and 12-13 are rejected under 35 U.S.C. 103 as being unpatentable over Suzuki et al (US 2010/0216096 A1, which is equivalent to EP 2 163 234 A1).
Suzuki teaches (see [0030]-[0031] and claim 1) a dental filling/restoration kit (equivalent to instant dental adhesive kit of claim 12) containing (A) a filling/restoring material (referred to as “a composite resin” hereinafter) and (B) a pretreatment material (referred to as “a primer” hereinafter): the composite resin (equivalent to instant dental photocurable composition) contains (i) 100 parts by mass of a radical-polymerizable monomer having no acidic group containing 3-30 parts by mass of a water-soluble radical-polymerizable monomer having no acidic group, (ii) a photopolymerization initiator, (iii) 80-2,000 parts by mass of a filler, (iv) a tertiary amine compound, and (v) a basic inorganic material; and the primer (equivalent to instant dental adhesive composition) contains (i) a radical-polymerizable monomer having an acidic group (instant polymerizable monomer (A-1) having an acidic group) and (ii) water.
In its working examples, Suzuki specifically teaches compositions of composite resin (see Tables 6 and 7) and compositions of primer (see Table 8). The primer composition “P10” (equivalent to instant dental adhesive composition) as shown in Table 8 (see also [0157], [0158] and [0186]) contains (i) PM, which is a mixture of 2-methacryloyloxyethyldihydrogen phosphate and bis(2-methacryloyloxyethyl) hydrogen phosphate (both of which teach instant polymerizable monomer (A-1) having an acidic group), (ii) water, (iii) IPA (isopropyl alcohol – instant volatile organic solvent (F)), (iv) BTPO (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide – Suzuki’s acylphosphine oxide-type photopolymerization initiator (see [0060] and [0064]) and (v) DMBE (ethyl p-N,N-dimethylamino benzoate – Suzuki’s tertiary amine compound (see [0090]-[0092], [0096]-[0097] and [0103]) (With respect to the components BTPO and DMBE, Suzuki teaches ([0091]) that by combining a tertiary amine compound (which examples include DMBE that is used in its primer composition P10) as a polymerization promoter with a photopolymerization initiator (which examples include BTPO that is used in its primer composition P10), the effect of the photopolymerization initiator is enhanced). Thus, at the outset, Suzuki’s primer composition “P10” contains instant polymerizable monomer (A) comprising (A-1) polymerizable monomer having an acidic group, instant volatile organic solvent (F) and instant water (G) that are contained in instant dental adhesive composition of claim 1.
With respect to instant photosensitizer (B) comprising an a-diketone compound, as already discussed above, Suzuki’s primer composition “P10” (instant dental adhesive composition) contains BTPO (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide) as its acylphosphine oxide-based photopolymerization initiator. Suzuki’s BTPO does not teach instant photosensitizer (B) comprising an a-diketone compound. However, Suzuki first teaches ([0061]-[0063] and [0075]) the equivalence of an a-keto carbonyl type photopolymerization initiator and an acylphosphine oxide type photopolymerization initiator, such as BTPO used in Suzuki’s primer composition “P10”. Suzuki then teaches ([0063]) that in terms of stability, a-diketones are preferably used as the a-ketone carbonyl type photopolymerization initiator. Based on Suzuki’s such teachings, it would have been obvious to one skilled in the art to use an a-diketone compound as Suzuki’s photopolymerization initiator (instead of BTPO) in its primer composition “P10” with a reasonable expectation of success in achieving stability. Thus, Suzuki teaches instant photosensitizer (B) comprising an a-diketone compound.
With respect to instant photopolymerization accelerator (D) comprising (D-1) aliphatic tertiary amine compound of Formula (I), although the DMBE (ethyl p-N,N-dimethylamino benzoate) used in Suzuki’s primer composition P10 is a tertiary amine compound, it does not meet instant Formula (1) of claim 1. However, Suzuki teaches ([0092] and [0104]) that as its tertiary amine compound, aromatic tertiary amine compounds (such as DMBE) or aliphatic tertiary amine compounds can be used and that these tertiary amine compounds may be used alone or in combination of at least two kinds of compounds. Suzuki further teaches ([0094]) that an aliphatic tertiary amine compound is preferably used for dental purposes in terms of the relatively low volatility and no generation of odor, and among the preferred examples (from the viewpoint of ease of availability and synthesis, chemical stability of the compound and excellent solubility in the polymerizable monomers) for the aliphatic tertiary amine compound, Suzuki teaches N-ethyldiallylamine and N-ethyldibenzylamine. Based on Suzuki’s such teachings, it would have been obvious to one skilled in the art to use an aliphatic tertiary amine compound such as N-ethyldiallylamine or N-ethyldibenzylamine (either instead of or in combination with the ethyl p-N,N-dimethylamino benzoate) as a polymerization promoter for the photopolymerization initiator (such as a-diketone as discussed above) in Suzuki’s primer composition P10 with a reasonable expectation of enhancing the effect of photopolymerization while reducing odor generation. N-ethyldiallylamine has the following structure:
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125
163
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, and N-ethyldibenzylamine has the following structure:
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147
114
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. Thus, Both of these compounds meet instant Formula 1 of claim 1: for the N-ethyldiallylamine, both instant R1 and R2 are aliphatic substituents consisting of 3 carbons having a vinyl group (instant electron-withdrawing group of claim 2) at a-carbon (as required in claim 3) and instant R3 is a substituent consisting of 2 carbons; for the N-ethyldibenzylamine, both instant R1 and R2 are substituents consisting of 7 carbon atoms having an aryl group (instant electron-withdrawing group of claim 2) at a-carbon (as required in claim 4) and instant R3 is a substituent consisting of 2 carbons. Furthermore, in each of the N-ethyldiallylamine and N-ethyldibenzylamine, the a-carbon of N in the formula is not one of the atoms that constitute the electron-withdrawing group. Thus, Suzuki’s N-ethyldiallylamine and N-ethyldibenzylamine both teach instant photopolymerization accelerator (D) of claims 1-4 comprising (D-1) aliphatic tertiary amine compound of Formula (1).
With respect to instant photoacid generator (C), even though Suzuki’s primer composition “P10” does not contain a photoacid generator, Suzuki teaches ([0070]) that when a photoacid generator is combined with a photopolymerization initiator in its dental filing/restoration kit, the polymerization activity can be enhanced more. Since Suzuki’s primer composition “P10” already contains a photopolymerization initiator, it would have been obvious to one skilled in the art to further include a photoacid generator in Suzuki’s primer composition “P10” in order to enhance the polymerization activity. Among the examples for the photoacid generator, Suzuki teaches ([0071] and [0073]) diaryliodonium salt compounds having cations such as diphenyliodonium and anions such as trifluoromethanesulfonate or tetrakis(pentafluorophenyl)borate. It would have been obvious to one skilled in the art to use a photoacid generator, which is a diaryliodonium salt compound having a diphenyliodonium cation (instant aryl iodonium cation of claim 9) and trifluoromethanesulfonate anion or tetrakis(pentafluorophenyl)borate anion (instant anions of claim 9 having (i) organic group in which at least one H is substituted with F and having (ii) S atom or B atom), in Suzuki’s primer composition “P10” with a reasonable expectation of enhancing the polymerization activity as taught by Suzuki. Thus, Suzuki teaches instant photoacid generator (C).
With respect to instant limitation “the one pack type dental adhesive composition comprises, . . . with respect to 100 parts by mass of a total of the (A) polymerizable monomer, the (F) volatile organic solvent and the (G) water in the case of containing the (G) water, . . . , 0.1 to 20 parts by mass of the (A-1) polymerizable monomer having an acidic group, 0.001 to 5 parts by mass of the (B) photosensitizer, 0.1 to 10 parts by mass of the (C) photoacid generator, 1 to 99.9 parts by mass of the (F) volatile organic solvent, and 0.01 to 20 parts by mass of the (D-1) aliphatic tertiary amine compound represented by Formula (1)”, in Suzuki’s primer composition “P10” shown in Table 8, there are 100 parts by mass of polymerizable monomers (50 parts by mass of PM (instant polymerizable monomer (A-1) having acidic group) and 50 parts by mass of HEMA (other polymerizable monomer)), 20 parts by mass of water and 85 parts by mass of isopropyl alcohol (instant volatile organic solvent). This means that per 100 parts by mass of total of the polymerizable monomers, volatile organic solvent and water, there are 24.4 parts by mass of PM (instant polymerizable monomer (A-1) having an acidic group), 41.5 parts by mass of the volatile organic solvent, 0.24 parts by mass of BTPO (Suzuki’s photopolymerization initiator, which is to be replaced with 0.24 parts by mass of a-diketone (instant photosensitizer), as already discussed above) and 0.24 parts by mass of DMBE (aliphatic tertiary amine compound, which is to be replaced with 0.24 parts by mass of N-ethyldiallylamine or N-ethyldibenzylamine (instant aliphatic tertiary amine compound of Formula (1)) as already discussed above), as calculated by the Examiner. Thus, Suzuki’s amounts for the volatile organic solvent (41.5 parts by mass), photosensitizer (0.24 parts by mass) and aliphatic tertiary amine compound of formula (1) (0.24 parts by mass) fall within instant ranges for the volatile organic solvent (1-99.9 parts by mass), photosensitizer (0.001-5 parts by mass) and aliphatic tertiary amine compound of Formula (1) (0.01-20 parts by mass). Although the amount (24.4 parts by mass) of “PM” (instant polymerizable monomer (A-1) having an acidic group) present in Suzuki’s primer composition “P10” falls outside of the claimed range (0.1-20 parts by mass), Suzuki gives a more general teaching ([0124]) that the polymerizable monomer having an acidic group (instant polymerizable monomer (A-1) having an acidic group) is contained in the primer of its dental filling/restoration kit in the amount of 10 parts by mass or more based on 100 parts by mass of the polymerizable monomers contained in the primer. Since there is a total of 205 (i.e., 50 + 50 + 20 + 85) parts by mass of the polymerizable monomers (PM and HEMA), water and organic solvent present in Suzuki’s primer composition “P10”, this first gives 10 parts by mass or more for the polymerizable monomer (“PM”) having an acidic group with respect to 205 parts by mass of the total of the polymerizable monomers, water and organic solvent. This converts to about 4.9 parts by mass or more for the PM (instant polymerizable monomer (A-1) having an acidic group) with respect to 100 parts by mass of a total of the (A) polymerizable monomer, the volatile organic solvent (F) and water (G). The range 4.9 parts by mass or more (as taught by Suzuki) overlaps with instant range of 0.1-20 parts by mass, thus rendering instant range prima facie obvious. In the case “where the [claimed] ranges overlap or lie inside ranges disclosed by the prior art,” a prima facie case of obviousness would exist which may be overcome by a showing of unexpected results, In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). With respect to the newly added limitation “0.1 to 10 parts by mass of the (C) photoacid generator”, as already explained above, even though Suzuki’s primer composition “P10” does not contain a photoacid generator, since Suzuki teaches that when a photoacid generator is combined with a photopolymerization initiator in its dental filing/restoration kit, the polymerization activity can be enhanced more, and Since Suzuki’s primer composition “P10” already contains a photopolymerization initiator, it would have been obvious to one skilled in the art to further include a photoacid generator in Suzuki’s primer composition “P10” in order to enhance the polymerization activity. Suzuki further teaches ([0074]) that the photoacid generator may be used in the amount of 0.001-12 pbw based on 100 pbw of the radical-polymerizable monomer contained in the composite resin. Based on such guideline, instant range (0.1 – 10 parts by mass) for the amount of photoacid generator to be contained in Suzuki’s primer composition “P10” would have been obvious to one skilled in the art before the effective filing date of the claimed invention since it has been held that where the general conditions of a claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. In re Aller, 105 USPQ 233. That is, determining the optimum amount for the photoacid generator to be used together with the photopolymerization initiator in Suzuki’s primer composition “P10” that would give the best polymerization activity would be within the realm of one of ordinary skill in the art. Thus, Suzuki’s teaching renders obvious instant limitation “the one pack type dental adhesive composition comprises, . . . with respect to 100 parts by mass of a total of the (A) polymerizable monomer, the (F) volatile organic solvent and the (G) water in the case of containing the (G) water, . . . , 0.1 to 20 parts by mass of the (A-1) polymerizable monomer having an acidic group, 0.001 to 5 parts by mass of the (B) photosensitizer, 0.1 to 10 parts by mass of the (C) photoacid generator, 1 to 99.9 parts by mass of the (F) volatile organic solvent, and 0.01 to 20 parts by mass of the (D-1) aliphatic tertiary amine compound represented by Formula (1)”.
With respect to instant preamble, “[a] one pack type dental adhesive composition”, Suzuki teaches ([0148]) that although there is no particular limit to the package form of the dental filling/restoration kit, it is more preferred that each item of the kit is packaged in the same container as one paste of a composite resin and one liquid of a primer (i.e., one pack for the composite resin paste (instant dental photocurable composition) and another pack for the primer liquid (instant dental adhesive composition)) for convenience of easy operation. Thus, Suzuki teaches instant one pack type dental adhesive composition.
Thus, Suzuki renders obvious instant claims 1-5, 9 and 13.
With respect to instant claim 12, as discussed above, Suzuki teaches a dental filling/restoration kit (instant dental adhesive kit) containing (A) a filling/restoring material (“a composite resin”) and (B) a pretreatment material (“a primer”). As also discussed above, Suzuki’s composite resin teaches instant dental photocurable composition) and its primer teaches instant dental adhesive composition. As discussed above, in its Tables 6 and 7, Suzuki teaches compositions of composite resin, and among those compositions shown in Tables 6 and 7, Suzuki specifically uses composite resin “CR4” together with its primer composition “P10” (see Example 27 in Table 10). In the composition of the composite resin “CR4” (instant dental photocurable composition) shown in Table 6, for 100 parts by mass of the polymerizable monomers contained in the composition, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BTPO) (instant photosensitizer) is present in the amount of 0.5 parts by mass. Thus, Suzuki renders obvious instant claim 12.
Response to Arguments
Applicant point out that instant claim 1 has been amended to require 0.1 to 10 parts by mass of the (C) photoacid generator (with respect to 100 parts by mass of a total of the (A) polymerizable monomer and the (F) volatile organic solvent or with respect to 100 parts by mass of a total of the (A) polymerizable monomer, the (F) volatile organic solvent and the (G) water in the case of containing the (G) water). Applicant point to [0069] of present specification and argue that by requiring the recited amount of the (C) photoacid generator, instant one pack type dental adhesive composition can suppress the occurrence wherein the polymerization promoting ability is poor and the curing becomes insufficient, and wherein the storage stability decreases. Applicant point to [0173] of the specification and argue that the storage stability of Examples R6 and R7 was reduced due to not containing the (C) photoacid generator (applicant ask the Examiner to also see comparative examples of the specification not containing the (C) photoacid generator). Applicant argue that in contrast to the claimed invention, Suzuki fails to disclose the presently required content of the (C) photoacid generator (relative to 100 parts by mass of a total of the (A) polymerizable monomer and the (F) volatile organic solvent or relative to 100 parts by mass of a total of the (A) polymerizable monomer, the (F) volatile organic solvent and the (G) water in the case of containing the (G) water). Applicant further argue that Suzuki is completely silent with respect to the above-described superior results (and thus fails to recognize the superior results) imparted by the presently required content of the (C) photoacid generator. Applicant argue that Suzuki’s composition P10 (equivalent to instant dental adhesive composition), which is relied upon in the rejection, does not contain a photoacid generator and thus, the storage stability of Suzuki’s composition P10 would be expected to be low in view of Examples R6 and R7 and the comparative examples of the present specification, which do not contain the (C) photoacid generator. Applicant argue that the superior results achieved by the presently claimed invention by requiring 0.1 to 10 parts by mass of the (C) photoacid generator (with respect to 100 parts by mass of a total of the (A) polymerizable monomer and the (F) volatile organic solvent or with respect to 100 parts by mass of a total of the (A) polymerizable monomer, the (F) volatile organic solvent and the (G) water in the case of containing the (G) water) would have been unexpected by one of ordinary skill in the art studying Suzuki’s teachings. Applicant accordingly argue that instant 103 rejection should be withdrawn.
The Examiner disagrees. Examples R6 and R7, to which applicant point to argue unexpected superior results of including instant (C) photoacid generator (in the claimed amount) in instant one pack type dental adhesive composition), are shown in Table 13, and for the following reasons, the data shown in Examples R1-R7 fail to show unexpected results of instant invention of claim 1, which is drawn to an one pack type dental adhesive composition that includes (C) photoacid generator (in the claimed amount):
Each of Examples R1-R7 (in Table 13) shows a dental adhesive kit, which is a combination of a Dental adhesive composition P4 , which does not contain any photoacid generator (see Table 1), and one of Dental curable compositions R1-R7 (see Table 6) in which compositions R1-R5 contain photoacid generators whereas compositions R6 and R7 do not contain any photoacid generator. Since the same Dental adhesive composition P4, which does not contain any (C) photoacid generator, is being used in each of Examples R1-R7 together with one of the Dental curable compositions R1-R7 (where the compositions R1-R5 contain photoacid generators whereas the compositions R6-7 do not contain any photoacid generator), the comparison between Examples R1-R5 vs. Examples R6-R7 in Table 13 is really about comparing dental curable compositions comprising photoacid generators vs. dental curable compositions not comprising any photoacid generator. That is, the comparison is not about comparing dental adhesive compositions comprising photoacid generators vs. dental adhesive compositions not comprising any photoacid generator (since all of Examples R1-R7 are using the same Dental adhesive composition P4, which does not contain any (C) photoacid generator). Therefore, the comparison between Examples R1-R5 vs. Examples R6-7 shown in Table 13 does not support applicant argument that by requiring the recited amount of the (C) photoacid generator in instant dental adhesive composition (of claim 1) one can suppress poor polymerization promoting ability, insufficient curing and decreased storage stability. Even though applicant argue that the storage stability of Examples R6 and R7 was reduced (when compared to Examples R1-R5) due to not containing the (C) photoacid generator (and thus argue that in view of the comparison of Examples R6-R7 to Examples R1-R5, the storage stability of Suzuki’s primer composition P10 (equivalent to instant dental adhesive composition), which does not contain a photoacid generator, would be expected to be low), Compositions R1-R5 (comprising photoacid generators) and Compositions R6-R7 (comprising no photoacid generator) used in Examples R1-R7 are applicant’s dental curable compositions, not dental adhesive compositions. Please note that instant invention of claim 1 is drawn to a dental adhesive composition comprising (C) photoacid generator, not to a dental curable composition comprising (C) photoacid generator. In fact, dental curable composition appears only in instant dependent claim 12 (which is drawn to a dental adhesive kit comprising a dental curable composition and the one pack type dental adhesive composition of claim 1), and the dependent claim 12 (as amended) does not even require (C) photoacid generator in the dental curable composition. Furthermore, although applicant ask the Examiner to also see the comparative examples of the specification not containing the (C) photoacid generator, in order to show unexpected superior results of including (C) photoacid generator (in the claimed amount) in instant dental adhesive composition of instant claim 1, applicant need to make a comparison between (i) instant dental adhesive composition of claim 1 containing all of instantly required components in the claimed amounts vs. (ii) a comparative dental adhesive composition that contains the same components (i.e., components that are the same both in kinds and amounts) except for the absence of the photoacid generator. That is, the only difference between the two dental adhesive compositions should be the presence or absence of the photoacid generator. Only then, one can fairly and directly ascertain the effect of having or not having the photoacid generator (C) (in the claimed amount) in instant dental adhesive composition. No such comparison is presented in present specification - see Tables 1 and 2 which show One Pack Type Dental Adhesive Compositions. Also, since applicant point to [0069] of present specification and argue that by requiring the recited amount (0.1-10 parts by mass) of the (C) photoacid generator, instant one pack type dental adhesive composition can suppress the occurrence wherein the polymerization promoting ability is poor and the curing becomes insufficient and wherein the storage stability decreases, in order to support such argument, applicant need to show the criticality of the claimed range for the amount of photoacid generator used in instant one pack type dental adhesive composition of claim 1. No such showing was made in present specification, either.
Therefore, for the reasons stated above, instant 103 rejection over Suzuki still stands.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIN J. LEE whose telephone number is (571)272-1333. The examiner can normally be reached on M-F 9 am-5:30pm.
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/SIN J LEE/
Primary Examiner, Art Unit 1613
November 3, 2025