DETAILED ACTION
Request for reconsideration of the application filed on 04/24/2026, is acknowledged. No amendment was made to the claims. Claims 1-2 ad 6-18 are pending in the application. Claims 6-11 and 13-18 have been withdrawn from consideration. Claims 1-2 and 12 are considered on merits.
In response to reconsideration, the examiner maintains rejections over prior art established in the previous Office 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 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.
Claim(s) 1-2 and 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Grayson (US 2015/0132854, IDS) in view of Eslinger et al. (WO 2010/020361).
Regarding claim 1, Grayson discloses a composition comprising at least one calibrant compound or a salt thereof (abstract), or a cationic complex thereof, or an anionic complex thereof (par [0018]),
wherein the at least one calibrant compound or the salt thereof or the cationic complex thereof, or the anionic complex thereof comprises an alcohol or an amine functionalized core and peripheral functionalities (Fig. 1, par [0077][0081]).
Grayson expressly teaches that the dendritic calibrants are synthesized by dendronization of hydroxyl-terminated core molecules, i.e., polyols bearing multiple hydroxyl groups that are chemically modified during synthesis.
Grayson states:
“The synthetic calibrants of the present disclosure are dendritic molecules—dendrimers—synthesized (‘generated’) via ‘dendronization’ of a hydroxyl-terminated core molecule and, optionally, a subsequent ‘deprotection’ step.” (par [0019])
Grayson further defines the core chemistry in terms of polyfunctional alcohols:
“[The dendrimers are synthesized] in parallel, wherein equimolar quantities of core molecules bearing different numbers of alcohol functionalities are mixed together and subjected to at least one round of dendronization.” (par [0020])
Thus, Grayson clearly establishes that the starting materials are polyols with multiple hydroxyl groups, i.e., functional groups that are chemically modifiable by esterification.
Importantly, Grayson does not state that bis-MPA anhydride is the only possible acylating reagent; rather, it exemplifies one implementation of modifying hydroxyl groups.
Grayson does not specifically disclose that wherein the peripheral functionalities are esters prepared by coupling the alcohol functionalities of the cores with a carboxylic acid selected from the group consisting of octanoic (caprylic) acid, nonanoic (pelargonic) acid, decanoic (capric) acid, undecanoic acid, dodecanoic (lauric) acid, tridecanoic acid, tetradecanoic (myristic) acid, pentadecanoic acid, hexadecanoic (palmitic acetic) acid, heptadecanoic (margaric acetic) acid, octadecanoic (stearic acetic) acid, nonadecanoic acid, eicosanoic (arachidic) acid, heneicosanoic acid, docosanoic (behenic) acid, tetracosanoic (lignoceric) acid, hexacosanoic (cerotic) acid, octacosanoic (montanic) acid, and triacosanoic (melissic) acid.
However, Eslinger discloses that wherein the peripheral functionalities are esters prepared by coupling the alcohol functionalities of the cores with a carboxylic acid selected from the group consisting of octanoic (caprylic) acid, nonanoic (pelargonic) acid, decanoic (capric) acid, undecanoic acid, dodecanoic (lauric) acid, tridecanoic acid, tetradecanoic (myristic) acid, pentadecanoic acid, hexadecanoic (palmitic acetic) acid, heptadecanoic (margaric acetic) acid, octadecanoic (stearic acetic) acid, nonadecanoic acid, eicosanoic (arachidic) acid, heneicosanoic acid, docosanoic (behenic) acid, tetracosanoic (lignoceric) acid, hexacosanoic (cerotic) acid, octacosanoic (montanic) acid, and triacosanoic (melissic) acid (page 4, par 1).
Eslinger teaches that “The plurality of fatty acid ester groups of the polyol polyester may comprise one or more fatty acids selected from the group consisting of anteisoarachadic, behenic, bosseopentaenoic acid, calendic, capric, caprylic, catalpic, eicosadienoic, eleostearic, erydiogenic, isomargaric, isomyristic, isostearic, jacaric, lauric, lesquerolic, licanic, linoleic, linolenic, myristic, oleic, palmitic, parinaric, punicic, ricinoleic, rumenic, ricinenic, and stearic acids.” (page 4, par 1).
Eslinger expressly teaches that polyols are esterified with fatty acids, including mixed fatty acids, using routine esterification chemistry.
Eslinger states: “The polyol polyester comprises a polyol residue and a plurality of fatty acid ester groups.” (page 7, lines 23-24).
Eslinger further explains: “The term ‘polyol residue’ as used herein means the core of the polyol molecule after one or more of the polyol hydroxyl groups have been reacted (converted) into an ester group.” (page 3, line 23-24).
And critically, Eslinger teaches that fatty acids are interchangeable design variables: “The fatty acids esterified to the polyol molecule may be mixed fatty acids to produce the desired physical properties.” (page 4, lines 20-21).
Thus, Eslinger provides an explicit teaching that:
polyol hydroxyl groups are esterified, and
fatty acids (including saturated and unsaturated, varied chain length) are routinely selected and substituted.
The motivation to apply Eslinger arises directly from Grayson’s disclosure of hydroxyl-terminated polyol cores and Eslinger’s disclosure of fatty-acid esterification of polyols.
Once Grayson teaches dendritic molecules built on polyol cores with multiple hydroxyl groups, a person of ordinary skill in the art would have recognized that those hydroxyl groups are chemically modifiable by known esterification reactions. Eslinger is reasonably pertinent because it teaches how polyol hydroxyl groups are esterified with fatty acids, including selection and variation of fatty acid substituents.
The motivation is therefore chemical compatibility and predictability, not coatings performance.
Furthermore, the rejection does not rely on Eslinger for a specific fatty acid mixture. Rather, Eslinger evidences that fatty acids are known reagents for esterification of polyol hydroxyl groups. Grayson teaches dendritic calibrant compounds synthesized from hydroxyl-functionalized polyol cores. One of ordinary skill in the art would have recognized that the hydroxyl functionalities disclosed by Grayson are amenable to esterification using known fatty acids, as taught by Eslinger, because esterification of polyol hydroxyl groups with fatty acids was a well-known and predictable chemical modification.
Regarding claim 2, Grayson discloses that wherein the at least one calibrant compound or the salt thereof or the cationic complex thereof, or the anionic complex thereof comprises at least one alcohol functionalized core selected from the groups consisting of:
mono-functional cores selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 3-methyl-1-butanol, 3-methyl-2-butanol, 2-methyl-1-butanol, and 2,2-dimethyl 1-propanol;
di-functional cores selected from the group consisting of ethylene glycol, 1,2-propane dial, 1,3-propane dial, 1,2-butane dial, 1,3-butane dial, 1,4-butane dial, 2,3-butane dial, 1,2-pentane dial, 1,5-pentane dial, 1,2-hexane dial, and 1,6-hexane dial;
tri-functional cores selected from the group consisting of 1,2,4-butane trial, 1,2,6-butane trial, 1, 1, 1-tris-(hydroxymethyl)ethane, and 1, 1, 1-tris(hydroxymethyl)propane;
tetra-functional cores selected from the group consisting of pentaerythritol, erythritol, and threitol;
penta-functional cores selected from the group consisting of xylitol, arabinitol, arabitol, adonitol, and triglycerol;
hexa-functional cores selected from the group consisting of dipentaerythritol, allitol, dulcitol, iditol, talitol, sorbitol, galactitol, and mannitol;
an octa-functional core selected from tripentaerythritol: and
dendrimer-based cores comprising at least one layer of bis-MPA repeating units bonding to any one of the mono-functional core, the difunctional core, the tri-functional core, the tetra-functional core, the pentafunctional core, the hexa-functional core, and the octa-functional core by esterification, and peripheral functionalities (par [0081][0166]).
Regarding claim 12, Grayson discloses that the calibrant composition comprising at least two compounds or salts thereof or cationic complexes thereof, or anionic complexes thereof, wherein the at least two calibrant compounds or the salts thereof comprise the alcohol or amine functionalized cores and the peripheral functionalities (par [0081][0166]).
Response to Arguments
Applicant's arguments filed 04/25/2026 have been fully considered but they are not persuasive.
Applicant's arguments have been fully considered but are not persuasive.
Applicant argues that Eslinger is directed to alkyd resins for paint coating compositions and does not disclose characteristics relating to spectroscopy, chromatography, CCS values, m/z values, gas-phase ion behavior, ion mobility, or mass spectrometry calibration (page 10). However, the rejection does not rely on Eslinger for such teachings. Rather, Eslinger is relied upon for its teaching that polyol hydroxyl groups may be esterified with fatty acids. A reference is not limited to the particular problem it seeks to solve and may be relied upon for all that it reasonably teaches to one of ordinary skill in the art.
Applicant further argues that Eslinger requires fatty acid esters containing conjugated double bonds and therefore teaches away from the use of saturated fatty acids (remark, page 10). This argument is not persuasive. A reference teaches away only when it criticizes, discredits, or otherwise discourages the claimed solution. Eslinger merely describes embodiments in which certain fatty acid esters contain conjugated double bonds. Such disclosure does not criticize, discredit, or discourage the use of saturated fatty acids. At most, Eslinger expresses a preference for particular embodiments useful in alkyd resin applications. A disclosure of preferred embodiments does not constitute a teaching away from alternative embodiments that would otherwise have been recognized by one of ordinary skill in the art.
Applicant argues that Eslinger requires a plurality of fatty acids whereas claim 1 requires a single carboxylic acid (remark, page 11). This argument is not persuasive. Claim 1 recites esterification using "a carboxylic acid selected from the group consisting of ..." and does not expressly require that only one carboxylic acid be present or used. The indefinite article "a" generally means "one or more" absent a clear intent to the contrary. Accordingly, the use of multiple fatty acids in Eslinger does not exclude the use of a carboxylic acid falling within the recited Markush group and therefore does not distinguish the claimed subject matter.
Therefore, the claimed composition encompasses embodiments in which esterification is performed using one or more fatty acids, including embodiments employing multiple fatty acids.
Furthermore, the rejection does not rely on Eslinger for a specific fatty acid mixture. Rather, Eslinger evidences that fatty acids are known reagents for esterification of polyol hydroxyl groups. Grayson teaches dendritic calibrant compounds synthesized from hydroxyl-functionalized polyol cores. One of ordinary skill in the art would have recognized that the hydroxyl functionalities disclosed by Grayson are amenable to esterification using known fatty acids, as taught by Eslinger, because esterification of polyol hydroxyl groups with fatty acids was a well-known and predictable chemical modification.
Applicant's assertion that the rejection is based on hindsight is not persuasive (remark, page 11-12). The motivation to combine arises from the teachings of the references themselves. Grayson teaches hydroxyl-functionalized dendritic cores and esterification chemistry. Eslinger teaches esterification of polyol hydroxyl groups with fatty acids. The combination merely applies a known esterification reagent to a known hydroxyl-functionalized substrate using recognized chemical principles and would have yielded predictable results.
Accordingly, the rejection of claims 1, 2, and 12 under 35 U.S.C. 103 is maintained.
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 XIAOYUN R XU, Ph. D. whose telephone number is (571)270-5560. The examiner can normally be reached M-F 8am-5pm.
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/XIAOYUN R XU, Ph.D./Primary Examiner, Art Unit 1797
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