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 .
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) in view of Matsushige et al (JP 2007-254307 and its English translation).
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 instant limitation “0.1 to 5 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. As to the amount of the photoacid generator, 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. Furthermore, Matsushige et al, a prior art which teaches (see abstract) a dental adhesive comprising an acidic-group-containing polymerizable monomer, a photoacid generator (such as a diaryl iodonium salt-based compound), an oxidation type photoradical generator (diaryl ketone compound) and an amine compound, teaches (see pg.25 of English translation, 4th paragraph) that the photoacid generator can be used in the amount of 0.1-10 parts by weight based on 100 parts by weight the acidic-group-containing polymerizable monomer. Based on such guidelines given by Suzuki and Matsushige, instant range (0.1 – 5 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 in view of the teaching of Matsushige 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 5 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 in view of Matsushige 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 in view of Matsushige renders obvious instant claim 12.
Response to Arguments
Applicant argue that the claimed one pack type dental adhesive composition can superiorly suppress the occurrence wherein the polymerization promoting ability is poor, the curing becomes insufficient and the storage stability decreases. Applicant argue that evidence in support of their argument can be found in present working examples and point specifically to Examples P7 and P8 as shown in Table 1 of present specification. Applicant point out that the photoacid generator (C) used in Example P7 is an aryl iodonium salt having an organic group and one or more atoms selected from P, B, Al, S and Ga and an aryl iodonium cation (and thus represents instant photoacid generator (C) of claim 1) whereas Example P8 does not include instant photoacid generator. Applicant argue that Examples P7 and P8 are substantially similar to each other and that one skilled in the art would reasonably expect that the difference in results is due to the presence or absence of the claimed photoacid generator (C). Applicant argue that it is clear from the comparison between Examples P7 and P8 that the results of Example P7 are better than that of Example P8 in suppressing the case where the polymerization promoting ability is poor, the curing becomes insufficient and the storage stability decreases: Applicant point to present Table 8 and argue that Example P7 is superior compared to Example P8, revealing superior storage stability achieved when using instant photoacid generator (C). Applicant argue that one skilled in the art studying Suzuki would not expect such effect and argue that Suzuki fails to disclose any examples directed to a one pack type dental adhesive composition containing the claimed photoacid generator (C) in the required amount. The Examiner disagrees. First of all, as already discussed above, 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 filling/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” (containing a photopolymerization initiator) so as to enhance the polymerization activity. As already discussed above, Suzuki teaches instant 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 anion 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). It would be obvious to one skilled in the art to use such photoacid generator in Suzuki’s primer composition “P10” with a reasonable expectation of enhancing the polymerization activity as taught by Suzuki. Secondly, applicant’s argument of superior result of their invention (containing the claimed photoacid generator (C)) is not found to be persuasive: (i) First of all, the comparison between Examples P7 and P8 is not a fair comparison because Example P8 contains DMPT (amine-based accelerator for polymerization) and BHT (a polymerization inhibitor), which are not contained in Example P7; (ii) Secondly, the photoacid generator C1 contained in Example P7 is bis(4-tert-butylphenyl)iodonium nonafluorobutane sulfonate, and such photoacid generator represents the preferred embodiment of dependent claim 9. Thus, the comparison made is not commensurate in scope with the broadest claim. See MPEP 716.02(d); (iii) besides, although applicant argue that the claimed one pack type dental adhesive composition can superiorly suppress the occurrence wherein the polymerization promoting ability is poor, such result would not be anything unexpected because Suzuki already teaches that when a photoacid generator is combined with a photopolymerization initiator the polymerization activity can be enhanced more.
For the reasons stated above, instant 103 rejection over Suzuki et al 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
July 11, 2026
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