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
Claim 1 has been amended to incorporate the limitations of claims 4-6. Claim 8 has been amended to correct a typographical error in the preamble. Support for the correction is found in claim 1. The rejection of claim 8 under 35 U.S.C. 112(b) has been overcome by amendment. Claims 4-6 and 12-14 are canceled. Claims 1-3, 7-11, and 15-20 are pending.
Response to Arguments
Applicant's arguments filed 09/23/2025 have been fully considered but they are not persuasive.
(p. 7) Applicants argue Lin does not disclose, teach, or suggest an overlapping range for 0.5-4 parts of a hydroxylation reagent selected from the group consisting of 1,2,3,4,5-pentitol, 1,2,3,4,5,6-hexanehexol and 2,2-dihydroxymethyl-butanol as recited in claim 1, as the office mistakenly concluded that trimethylolpropane (TMP) is also known as 2,2-dihydroxymethyl-butanol (also known as 2,2-bis(hydroxymethyl)-1-butanol, trimethylolethane, or TME), which is recited in claim 1.
The examiner respectfully disagrees with applicants’ assertion that trimethylolpropane is not also known as 2,2-dihydroxymethyl-butanol. Both names are synonyms for the molecule described by CAS number 77-99-6, as evidenced by Chemeo.
(p. 7-9) Applicants argue a skilled artisan would not have been motivated to modify Lin's hydroxyl-terminated resin composition by adding 1-5% mass% tert-butyl glycidyl carbonate and 0.3-0.5 mass% of an antioxidant from Ying due to the distinct application/purposes of the compositions of Lin and Ying. Applicants argue that the Lin composition provides a texture powder coating with strong layering and good mechanical properties. In contrast, Ying is directed to topcoat powder coatings with good transparency and leveling. Mechanical properties are typically not as important for topcoats, whereas transparency is typically not desired for basecoats (opacity is typically desired for basecoats). The necessary properties for base coats and top coats make them non-substitutable for the other. Stated another way, the problems addressed by Lin and Ying are distinct and, as a result, their compositions and properties of the compositions are distinct.
In response to applicant's argument that Ying is nonanalogous art, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992).
In this case, the examiner maintains that the compositions of Lin and Ying are both directed toward powder coating applications, which is a shared field of endeavor. Furthermore, Lin teaches that good weather resistance is desirable for powder coatings [p. 0023], and Ying et al teaches the use of tert-butyl glycidyl carbonate increases the water resistance of the resin powder coating [p. 0030], therefore Lin and Ying address related problems.
(p. 10) Applicants argue, regarding claim 8, Lin's hydroxyl value of 25~35 mg KOH/g is aimed at balancing texture effects and mechanical properties. The hydroxyl value of Lin has a lower limit of 25 mg KOH/g to ensure the mechanical properties of the coating. However, the present application achieves a breakthrough in reducing the hydroxyl value to 20-30 mg KOH/g through the introduction of glycidyl tertcarbonate and the staged vacuum process, while achieving two major technical and economic effects: (1) reducing the amount of curing agent by 30%, and significantly reducing raw material costs, and (2) a low crosslink density. Lin and Ying have no disclosures, teachings, or suggestions for realizing the features of the present invention. In fact, Lin explicitly excludes the possibility of hydroxyl values of <25 mg KOH/g.
Applicant's arguments do not comply with 37 CFR 1.111(c) because they do not clearly point out the patentable novelty which he or she thinks the claims present in view of the state of the art disclosed by the references cited or the objections made. Further, they do not show how the amendments avoid such references or objections.
Here, applicants argue that Lin excludes the possibility of hydroxyl values <25 mg KOH/g, however, applicants claim the hydroxyl value of the polyester resin product is 20-30 mg KOH/g [claims 2 and 8]. Lin's hydroxyl value of 25-35 mg KOH/g. ]. 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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
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 1-3, 7-11, and 15-20 are rejected under 35 U.S.C. 103 over Lin et al (CN 106832236 A) in further view of Ying et al (CN 104311806 B) as evidenced by Kezios et al (US 2007/0128389 A1).
All references to Lin et al and Ying et al are directed at the English machine translation.
Lin et al teaches a hydroxyl-terminated polyester resin for powder coating obtained by melt polycondensation of the following components by mass fraction:
35-40% diol, including at least neopentyl glycol and further comprising one or both of 2-methylpropanediol and ethylene glycol;
48-70% diacid, comprising 43-52% terephthalic acid, 5-14% isophthalic acid, and 0-4% succinic acid;
1.8-3% triol, comprising 0-3 % trimethylolpropane (2,2-dihydroxymethyl-butanol) and 0-3 % 1,2,6-hexanetriol, reading over the hydroxylation agent of instant claims 1, 6, and 14; and
0.05-0.12% catalyst, selected from monobutyltin oxide or dihydroxybutyltin chloride [p. 0011-0022].
Lin et al teaches the polyester resin has a hydroxyl value of 25 to 35mgKOH/g; an acid value of less than 8 mg KOH/g, a glass transition temperature of 58 to 65°C, and a melt viscosity of 7000 to11000 mPa·s [p. 0006, 0023]. 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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Lin et al teaches the polyester resin used to prepare weather-resistant powder coatings may contain other auxiliary agents [p. 0024], however, Lin et al is silent with respect to the glycidyl tertcarbonate and antioxidant components.
Ying et al teaches a polyester resin for high-leveling transparent powder coatings [p. 0010]. Ying et al teaches the use of 1-5 mass% tert-butyl glycidyl carbonate in the preparation of the polyester resin [p. 0017]. Ying et al teaches the molecular chain structure of the polyester resin changes due to the introduction of tertiary carbonic acid glycidyl ester with a larger tertiary carbon side group, resulting in a disruption of the regularity of the polyester resin molecular chain segment, a reduction of the crystallinity of the polyester resin molecule, and thereby improves the transparency of the transparent powder coating made therefrom, providing a coating film with a relative light transmittance of more than 98% [p. 0030]. Ying et al further teaches the side group of the tert-butyl carbon structure increases the hydrolysis stability of the ester group. The resin coating prepared by using tert-butyl glycidyl carbonate has good water resistance, acid and alkali resistance and weather resistance. Therefore, the powder coating film prepared by it has excellent leveling, high-gloss, fullness, excellent clarity and good comprehensive performance, and can be used in the field of topcoat, such as an automotive topcoat, automotive wheel hub, metal furniture and hard plastic topcoat [p. 0030].
Furthermore, Ying teaches the use of 0.3-0.5 mass % of a hindered phenol antioxidant [p. 0020]. Ying et al teaches after cooling and crushing the polyester resin composition, a colorless or light yellow transparent granular material is obtained [p. 0039]. Hindered phenolic antioxidants are known in the art to provide polyester resins with improved color as understood by a low yellowness index and improved clarity characteristics as understood as a high visible light transmittance, as evidenced by Kezios et al [p. 0100-0101]
Ying et al teaches powder coating films with transparency and excellent clarity can be used as topcoats in the automotive industry and others. Lin et al is interested in the use of powder coating films in the automotive industry (ex. car bumpers) [p. 0004]. In light of this, it would have been obvious to one having ordinary skill in the art at the time the invention was file to prepare the composition of Lin et al with 1-5 mass% tert-butyl glycidyl carbonate and 0.3-0.5 mass % of an antioxidant to improve the transparency and clarity characteristics of the hydroxyl-terminated resin composition.
Lin et al teaches a method of preparation of the hydroxyl-terminated polyester resin in a nitrogen atmosphere [p. 0022, 0027]:
In a 100L reactor, add a proportion of trimethylolpropane and/or neopentyl glycol, heat to 140°C to melt the materials; then add a proportion of terephthalic acid, isophthalic acid, succinic acid and catalyst monobutyltin oxide in sequence, pass nitrogen and continue to heat to react until esterification water begins to form and distill at 175°C;
Heating and heat preservation: then gradually heat to 240°C at a rate of 1-1.5°C/10min, and keep at 240°C until the column top temperature is lower than 70°C. After the material becomes clear and transparent, the sample acid value is 13.5mgKOH/g, and the melt viscosity is 2000 mPa·s (ICI cone and plate viscometer, 200°C);
Polycondensation under reduced pressure: cool to 220°C, vacuuming and polycondensing for 1h, release the vacuum, the acid value reaches 7.2mgKOH/g, and the melt viscosity is 6300mPa·s (ICI cone and plate viscometer, 200°C);
cool to 210°C, vacuuming and polycondensing for 1h, release the vacuum, the acid value reaches 4.8mgKOH/g, and the melt viscosity is 10100 mPa·s (ICI cone and plate viscometer, 200°C)
Discharge: filter, cool, crush and package to obtain low hydroxyl-terminated hydroxyl polyester resin
Regarding claim 8 step (a),
Ying et al, as relied upon for the addition of a glycidyl tertcarbonate component, teaches the glycidyl tertcarbonate component is added in the initial monomer feed, therefore, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to also add the glycidyl tertcarbonate in the initial monomer feed when preparing the composition of Lin et al with glycidyl tertcarbonate for increased transparency [p. 0023].
Regarding claim 8 step (b), Lin et al teaches esterification is continued until 95% of the esterification water is discharged and the acid value reaches 10 to 15 mg KOH/g.
Regarding claim 8 step (c), Lin et al teaches condensation is continued the acid value reaches 3 to 8 mg KOH/g, and the viscosity reaches 7000 to 11000 mPa·s. Lin et al further teaches the hydroxyl-terminated polyester resins preferably have a hydroxyl value of 25-35 mg KOH/g.
Lin et al teaches the trimethylolpropane (hydroxylation reagent) is added in the in the initial monomer feed during the preparation of the hydroxyl-terminated polyester resin [p. 0025]. Applicants claim the hydroxylation agent was added in a second feed, after vacuumizing, presumably to achieve a hydroxyl-terminated polyester resin. As Lin et al also achieves a hydroxyl-terminated polyester resin, and the applicants fail to exemplify any differences in order of addition, the applicants are reminded selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results. See MPEP 2144.04.IV.C.
Furthermore, Ying et al, as relied upon for the addition of an antioxidant component, teaches the antioxidant component is added in the final step of the preparation of the polyester composition, therefore, it would have been obvious to one having ordinary skill in the art at the time the invention was filed to also add the antioxidant in the final step of the preparation of the polyester composition when preparing the composition of Lin et al with glycidyl tertcarbonate for increased degree of clarity [p. 0028].
Regarding instant claim 9, Lin et al teaches polycondensation occurs under vacuum and exemplifies a vacuum degree of -0.09 MPa [p. 0027]. Lin et al does not provide a limitation to the degree of vacuuming during the polycondensation step. Lin et al teaches the first vacuum polycondensation step is complete when the acid value reaches 7.2mgKOH/g, and the melt viscosity is 6300mPa·s (ICI cone and plate viscometer, 200°C). The degree in of vacuum during vacuum polycondensation is a result effective variable as the degree of vacuum dictates the rate in which condensates are removed, and therefore effects the amount of time the polycondensation takes to complete. The determination of the optimum or workable range of vacuum applied is characterized as routine experimentation, as seen in Ying et al, as relied upon for the addition of the glycidyl tertcarbonate component and antioxidant component to a polyester resin composition. Ying et al teaches the polycondensation under vacuum is performed at -0.090 - 0.094 Mpa for 60-80 min [p. 0026-0027]. The teachings of Ying et al support the result effective relationship between degree of vacuum and amount of time the vacuum polycondensation takes to reach completion. Lin et al teaches the first vacuum polycondensation step is complete when the acid value reaches 7.2mgKOH/g, and the melt viscosity is 6300mPa·s. Therefore, it would be obvious to one having ordinary skill in the art to optimize the degree of vacuum in order to achieve the desired acid value and viscosity taught by Lin et al. “[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.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05.II.A.
Regarding claim 16, Lin et al teaches the polycondensation is performed at 240°C. 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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claim 17, Lin et al is silent with respect to the length of the initial esterification step. As Lin et al teaches the esterification step is continued until 95% or more of the theoretical esterification water output is reached [p. 0022]. Although Lin et al is silent with respect to the length of time necessary to complete the polycondensation, the duration of the polycondensation is a result effective variable as the reaction duration dictates the degree of condensation. The determination of the optimum or workable range of reaction duration is characterized as routine experimentation. Lin et al teaches the degree of condensation can be determined by the amount of condensate collected relative to the theoretical amount of condensate. Therefore, it would be obvious to one having ordinary skill in the art to optimize the reaction duration in order to achieve a degree of esterification of 95% or greater. “[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.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05.II.A.
Regarding claim 18, Lin et al teaches the second polycondensation reaction occurs over 60 minutes. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Regarding claim 19, Lin et al does not teach the addition of an hydroxylation agent as a separate step, as discussed above, however the hydroxylation reaction of applicant’s step (c) is a condensation reaction, akin to the condensation reactions of step (a) and step (b). Lin et al teaches that after the esterification has reached 95% and the acid value reaches 10 to 15 mg KOH/g, the reaction is cooled to 220 °C and polycondensation proceeds for 1 hour, wherein the acid value reaches 7.2 mg KOH/g and the melt viscosity is 6300mPa·s [p. 0022, 0027]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Regarding claim 20, Ying et al, as relied upon for the addition of an antioxidant component, teaches the temperature is lowered to 200 °C after vacuum is released, and the antioxidant component F is added and stirred for 15-30 minutes [p. 0027]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to HOLLEY GRACE HESTER whose telephone number is (703)756-5435. The examiner can normally be reached Monday - Friday 9:00AM -5:00PM.
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/HOLLEY GRACE HESTER/ Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/ Supervisory Patent Examiner, Art Unit 1766