DETAILED ACTION
The amendment and RCE filed on 12/19/2025 has been entered and fully considered. Claims 1-2 and 6-18 are pending. Claims 6-11 and 13-18 have been withdrawn from consideration. Claims 1-2 and 12 are considered on merits, of which claim 1 is amended.
Response to Amendment
In response to amendment, the examiner maintains rejection over the 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.
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 12/19/2025 have been fully considered but they are not persuasive.
Applicant argues that Eslinger is directed to alkyd resins and paint coatings and therefore provides no motivation to modify the dendritic calibrant molecules of Grayson. This argument is not persuasive.
1. Grayson Teaches Hydroxyl-Terminated Polyol Cores Amenable to Esterification
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.
2. Eslinger Teaches Esterification of Polyols with Fatty Acids as a Known Chemical Modification
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.
3. Motivation: Applying Known Polyol Esterification Chemistry to Grayson’s Polyol Cores
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.
4. Eslinger Need Not Teach Spectroscopy or CCS Behavior
Applicant argues that Eslinger does not discuss CCS values, m/z behavior, ion mobility, or MS calibration. However, the claims are directed to chemical compositions, not to a particular analytical theory.
A reference need not recognize the same advantage or end use to provide motivation. The Office relies on Eslinger for its teaching of esterifying polyol hydroxyl groups with fatty acids, not for analytical performance metrics.
Discovery of a new property (e.g., CCS behavior) of an otherwise obvious structure does not render the structure non-obvious.
5. Conclusion
Grayson teaches dendritic calibrant molecules synthesized from hydroxyl-terminated polyol cores. Eslinger teaches that polyol hydroxyl groups are routinely esterified with fatty acids, and that fatty acid identity is a selectable variable. A person of ordinary skill in the art would therefore have been motivated to apply Eslinger’s known fatty-acid esterification chemistry to the polyol cores of Grayson to obtain esterified dendritic molecules.
Accordingly, the motivation to combine Grayson and Eslinger is supported by the record, and the rejection under 35 U.S.C. §103 is maintained.
Conclusion
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Lyle Alexander can be reached on 571-272-1254. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/XIAOYUN R XU, Ph.D./Primary Examiner, Art Unit 1797