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 .
DETAILED ACTION
Claims 1-10 are pending in the application. Claims 1-10 are rejected.
Priority
3. The instant application 18/474,204, filed on September 25th 2023 claims priority under 35 U.S.C. 119(a)-(d), to TW112128259, filed on July 28th, 2023. Although the certified copies have been filed, only an English translation of the abstract is provided.
Receipt is acknowledged of a certified copy of foreign application; however, the present application does not properly claim priority to the submitted foreign application. If this copy is being filed to obtain priority to the foreign filing date under 35 U.S.C. 119(a)-(d) or (f), 365(a) or (b), or 386(a), applicant must also file a claim for such priority as required by 35 U.S.C. 119(b) or 365(b), and 37 CFR 1.55. If the application was filed before September 16, 2012, the priority claim must be made in either the oath or declaration or in an application data sheet; if the application was filed on or after September 16, 2012, the claim for foreign priority must be presented in an application data sheet.
If the application being examined is an original application filed under 35 U.S.C. 111(a) (other than a design application), the claim for priority must be presented during the pendency of the application, and within the later of four months from the actual filing date of the application or sixteen months from the filing date of the prior foreign application. See 37 CFR 1.55(d)(1). If the application being examined is a national stage application under 35 U.S.C. 371, the claim for priority must be made within the time limit set forth in the PCT and Regulations under the PCT. See 37 CFR 1.55(d)(2). Any claim for priority under 35 U.S.C. 119(a)-(d) or (f), 365(a) or (b), or 386(a) not presented within the time period set forth in 37 CFR 1.55 is considered to have been waived. If a claim for foreign priority is presented after the time period set forth in 37 CFR 1.55, the claim may be accepted if the claim properly identifies the prior foreign application and is accompanied by a grantable petition under 37 CFR 1.55(e) to accept an unintentionally delayed claim for priority and the applicable petition fee under 37 CFR 1.17(m)(1) or (m)(2).
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 10/10/2024, 10/22/2024 and 03/28/2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
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 the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
7. Claims 1, 2, 4-6, 8, and 10 are rejected under 35 U.S.C 103 as being unpatentable over Yin et al. (Continuous heterogeneous isomerization of 3/4-methyltetrahydrophthalic anhydride (3/4-MTHPA) with acid- and base-modified γ-Al2O3 catalysts, New J. Chem., 2023,47, pp. 1256-1267) herein referred as Yin.
As to claim 1, Yin teaches a method for isomerizing methyltetrahydrophthalic anhydride, comprising: providing a liquid reactant which includes 3-methyltetrahydrophthalic anhydride and 4-methyltetrahydrophthalic anhydride (Page 1256, Abstract; isomerization of 3/4-methyl-tetrahydro phthalic anhydride; Page 1258, paragraph 2, 2.3. Catalytic activity measurements: 3-MTHPA was used as the reactant for the isomerization reaction in the reaction system).
Yin further teaches under a condition that nitrogen gas is injected (Page 1258, paragraph 1, 2.3. Catalytic activity measurements: the air in the reactor was replaced with N2, about 3–4 times),
adding an alkaline catalyst into the liquid reactant for an isomerization reaction, so as to obtain an isomerization product (Page 1256, Abstract, A series of acid–base-loaded γ-Al2O3 catalysts was applied as the catalysts for the isomerization of 3/4-methyl-tetrahydro phthalic anhydride);
wherein, based on a total weight of the isomerization product (Page 1266, 6. Conclusions; the conversion rate of the basic isomerism reached 80%);
an amount of a methyltetrahydrophthalic anhydride dimer (Page 1256, Abstract-activity loss was 4.6%-6.6%)
Yin does not explicitly teach that the total weight of the isomerization product is 100 wt.% or that an amount of a methyltetrahydrophthalic anhydride dimer is lower than 1.6 wt.%. It should be noted that there is no evidence that this dimer impurity is formed during an isomerization reaction.
Applicants are reminded that the office does not have the facilities and resources to provide the factual evidence needed in order to establish that the product of the prior art does not possess the same material, structural and functional characteristics of the claimed product. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed product is different from those taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the series of acid–base-loaded γ-Al2O3 catalysts as the alkaline catalysts for the isomerization of 3/4-methyl-tetrahydro phthalic anhydride with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification for the benefit of obtaining an isomerization product by isomerizing methyltetrahydrophthalic anhydride with minimal dimer formation.
As to claim 2, Yin teaches the method of claim, wherein the liquid reactant is carried out for the isomerization reaction at a temperature ranging from 140°C to 160°C (Page 1266, paragraph 3, 5.6 Design of the 3/4-MTHPA isomerization reaction process; the reaction was carried out at 150-165 °C). Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have optimized Yin’s suitable reaction temperature within the claimed range in order to carry out an isomerization reaction with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification for the benefit of obtaining maximum amount of the isomerization product by isomerizing methyltetrahydrophthalic anhydride.
As to claim 4, Yin teaches the method of claim 1, wherein the nitrogen gas is injected into the liquid reactant (Page 1258, Paragraph 1, 2.3 Catalytic activity measurements-the air in the reactor was replaced with N2, about 3–4 times) before adding the alkaline catalyst (Page 1256, Abstract-K, Na or the like) into the liquid reactant for the isomerization reaction (Page 1258, 2.3 and 5.6-As depicted in Fig. 18, after the reactor was installed, the air in the reactor was replaced with N2. The reactor was connected to a tubular fixed-bed reactor. The first section of the pipeline introduced the basic catalyst in the tube).
Regarding claim limitation, “so as to remove oxygen gas and water vapor present in the liquid reactant”, because prior art teaches all the steps of the reaction; Yin teaches a method for isomerizing methyltetrahydrophthalic anhydride, comprising: providing a liquid reactant which includes 3-methyltetrahydrophthalic anhydride and 4-methyltetrahydrophthalic anhydride; then adding the nitrogen gas and then adding an alkaline catalyst, it would necessarily remove the oxygen gas and the water vapor present in the liquid reactant. The burden is on applicant to show that it does not. A recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Applicants are reminded that the office does not have the facilities and resources to provide the factual evidence needed in order to establish that the product of the prior art does not possess the same material, structural and functional characteristics of the claimed product. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed product is different from those taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
As to claim 5, Yin teaches the method of claim 4, wherein the nitrogen gas is injected into the liquid reactant in a form of bubbles (Page 1258, paragraph 1, 2.3 Catalytic activity measurements-the air in the reactor was replaced with N2, about 3–4 times; 2.4 Catalyst characterization-nitrogen gas injected into a liquid reactant where the nitrogen was used as the adsorption medium).
Regarding claim limitation, “so as to remove oxygen gas and water vapor present in the liquid reactant”, because prior art teaches all the steps of the reaction; Yin teaches a method for isomerizing methyltetrahydrophthalic anhydride, comprising: providing a liquid reactant which includes 3-methyltetrahydrophthalic anhydride and 4-methyltetrahydrophthalic anhydride; then adding the nitrogen gas and then adding an alkaline catalyst, it would necessarily remove the oxygen gas and the water vapor present in the liquid reactant. The burden is on applicant to show that it does not. A recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Applicants are reminded that the office does not have the facilities and resources to provide the factual evidence needed in order to establish that the product of the prior art does not possess the same material, structural and functional characteristics of the claimed product. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed product is different from those taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
As to claim 6, Yin teaches the method of claim 1, wherein the liquid reactant is carried out for the isomerization reaction in a reactor (Page 1256, Abstract, fixed-bed reactor; Page 1258, paragraph 1, 2.3 Catalytic activity measurements-20 mL of MTHPA was placed in a high-temperature and high-pressure reactor), and the nitrogen gas is injected into the reactor (Page 1258, paragraph 1, 2.3 Catalytic activity measurements-the air in the reactor was replaced with N2, about 3–4 times).
Regarding claim limitation, “so as to remove oxygen gas and water vapor present in the liquid reactant”, because prior art teaches all the steps of the reaction; Yin teaches a method for isomerizing methyltetrahydrophthalic anhydride, comprising: providing a liquid reactant which includes 3-methyltetrahydrophthalic anhydride and 4-methyltetrahydrophthalic anhydride; then adding the nitrogen gas and then adding an alkaline catalyst, it would necessarily remove the oxygen gas and the water vapor present in the liquid reactant. The burden is on applicant to show that it does not. A recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Applicants are reminded that the office does not have the facilities and resources to provide the factual evidence needed in order to establish that the product of the prior art does not possess the same material, structural and functional characteristics of the claimed product. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed product is different from those taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
As to claim 8, Yin teaches the method according to claim 1.
Yin further teaches that based on a total weight of the liquid reactant being 100 phr, an amount of the alkaline catalyst ranges from 0.5 phr to 1.5 phr (Page 1262, paragraph 4, 5.1.3 Basic isomerization of 3-MTHPA and Figure 13. Catalytic activity of catalysts for 3-MTHPA under different conditions.). Although “phr” isn’t explicitly stated, the Google translation of instant priority application states that “the amount of the alkaline catalyst added is 0.5 to 1.5 parts by weight based on the total weight of the liquid reactant being 100 parts by weight.” That is to say, phr is equivalent to Yin’s part per 100. Yin teaches the effect of the catalyst amount on the isomerization reaction; when the amounts of catalyst were 0.5, 1,2,3, and 4%, the conversion rate of 3% was the best (Page 1262, paragraph 4, 5.1.3 Basic isomerization of 3-MTHPA and Figure 13. Catalytic activity of catalysts for 3-MTHPA under different conditions.)
As to claim 10, Yin teaches a method according to claim 1, wherein a weight ratio of 3-methyltetrahydrophthalic anhydride to 4-methyltetrahydrophthalic anhydride in the liquid reactant ranges from 7:3 to 3:7. (Page 1265, Paragraph 4, 5.5 Product performance of MTHPA; isomerization of 3/4-MTHPA with the optimal mixing ratio of 3:4 = 1.5:1; a ratio that falls within the claimed range in the liquid reactant).
8. Claim 3 is rejected under 35 U.S.C 103 as being unpatentable over Yin et al. (Continuous heterogeneous isomerization of 3/4-methyltetrahydrophthalic anhydride (3/4-MTHPA) with acid- and base-modified γ-Al2O3 catalysts, New J. Chem., 2023,47, pp. 1256-1267) in view of Tani et al. (Process for Production of Methyltetrahydrophthalic Anhydride (USPN 5,237,074)) herein referred as Tani.
As to claim 3, Yin teaches the method of claim 1, wherein the liquid reactant is carried out for the isomerization reaction under a condition that nitrogen gas is continuingly injected (Page 1258, Paragraph 1, 2.3. Catalytic activity measurements: the air in the reactor was replaced with N2, about 3–4 times),
Yin does not explicitly teach wherein a volume flow rate of the nitrogen gas ranges from 0.4 L/hour to 0.8 L/hour.
Tani teaches wherein a volume flow rate of the nitrogen gas ranges from 0.4 L/hour to 0.8 L/hour (col 7, lines 54-56; nitrogen gas was passed at a rate of 10 ml/min throughout the reaction period which is equal to 0.6L/hour according to the following calculation:
10ml/min * 1L/1000 ml + 0.01 L/min
0.01 L/min * 60 min/hour = 0.6 L/hour).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have optimized Yin’s teachings with Tani’s volume flow rate of the nitrogen gas within 0.4 L/hour to 0.8 L/hour range in order to carry out an isomerization reaction with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification for the benefit of obtaining maximum amount of the isomerization product by isomerizing methyltetrahydrophthalic anhydride. Using such a method would make it possible to obtain a high yield of product while suppressing the formation of gels.
9. Claims 7 and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Yin et al. as applied to claim(s) 1-6 above, and further in view of Ariga et al. (Process for stereoisomerization of cis-3-methyl-Δ4 -tetrahydro-cis,cis-phthalic anhydride (USPN4198340A)) herein referred as Ariga.
As to claim 7, Yin teaches the method according to claim 1.
Yin does not explicitly teach a weight ratio of trans-3-methyltetrahydrophthalic anhydride to cis-3-methyltetrahydrophthalic anhydride in the isomerization product ranges from 4:1 to 5:1.
Ariga teaches the weight ratios (Abstract: A mixture of said compounds (1) and (2) in a ratio by weight of 7:3 to 2:8 obtained by the isomerization reaction; said compounds: (1) cis-3-methyl- DELTA 4-tetrahydro-cis, cis-phthalic anhydride and (2) trans-3-methyl- DELTA 4-tetrahydro-cis, cis-phthalic anhydride).
It would have been obvious to a person having ordinary skill in the art before the effective filing date to replace the isomerization product within the teachings of Yin with Ariga’s isomerization product of trans-3-methyltetrahydrophthalic anhydride to cis-3-methyltetrahydrophthalic anhydride in in order to expect reasonable success in achieving their optimum weight ratios. Using Ariga’s weight ratio example, one of ordinary skill in the art would have been motivated to make this modification for the benefit of obtaining maximum weight ratios of the isomerization product by isomerizing methyltetrahydrophthalic anhydride making it more suitable for commercial-scale production.
In addition, with respect to the weight ratio being in a range from 4:1 to 5:1, Ariga discloses the general conditions for this ratio.
"[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." MPEP 2144.05(II)
Applicants are reminded that the office does not have the facilities and resources to provide the factual evidence needed in order to establish that the product of the prior art does not possess the same material, structural and functional characteristics of the claimed product. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed product is different from those taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
As to claim 9, Yin teaches the method according to claim 1.
However, Yin does not disclose wherein a weight ratio of trans-3-methyltetrahydrophthalic anhydride to cis-3-methyltetrahydrophthalic anhydride in the liquid reactant ranges from 1:4 to 1:7.
Ariga teaches wherein a weight ratio of trans-3-methyltetrahydrophthalic anhydride to cis-3-methyltetrahydrophthalic anhydride in the liquid reactant ranges from 1:4 to 1:7 (col 2, lines 42-47-stopping the reaction when a mixture of cis and trans tetrahydro in a weight ratio reaches 7:3 to 2:8 where 2:8 is within the range of 1:4).
It would have been obvious to a person having ordinary skill in the art before the effective filing date to modify Yin’s liquid reactant with Ariga’s at the stated ratio. One of ordinary skill in the art would have been motivated to make this modification for the benefit of obtaining immediate and assured effect as compared with other techniques and also provides more freedom from the drawback that isomerization reaction further proceeds upon heat involved in distilling the resulting mixture for purification.
Conclusion
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/SAHAR INAM/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622